Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520621004492/eb5068sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb50680minUVsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068140minUVsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068270minUVsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068530minUVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068660minUVsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068790minUVsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068920minUVsup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb50681050minUVsup9.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb50681290minUVsup10.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb50681950minUVsup11.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb50680minUV_01GPasup12.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb50680minUV_075GPasup13.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb506810hUV_075GPasup14.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb506844hUV_075GPasup15.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb506844hUV_01MPasup16.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb50680minUV_1GPasup17.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068140minUV_1GPasup18.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068270minUV_1GPasup19.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068400minUV_1GPasup20.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068580minUV_1GPasup21.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068760minUV_1GPasup22.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb5068940minUV_1GPasup23.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb50681120minUV_1GPasup24.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb50681300minUV_1GPasup25.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520621004492/eb50681_5gpa_144huvsup26.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520621004492/eb5068sup27.cml |
CCDC references: 2040773; 2040774; 2040775; 2040776; 2040777; 2040778; 2040779; 2040780; 2040781; 2040782; 2040783; 2040784; 2040785; 2040786; 2040787
Data collection: CrysAlis PRO (Agilent Technologies, 2014) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa; Bruker APEX2 for 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa; Diamond Light Source, beamline I-19 for 1_5gpa_144huv. Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa, 1_5gpa_144huv; Bruker SAINT for 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa. Data reduction: CrysAlis PRO (Rigaku OD, 2015) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa, 1_5gpa_144huv; Bruker SAINT for 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa. Program(s) used to solve structure: SHELXT 2014/5 (Sheldrick, 2014) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa, 1_5gpa_144huv; SHELXS2013/1 (Sheldrick, 2008) for 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa. Program(s) used to refine structure: SHELXL 2014/7 (Sheldrick, 2015) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa; SHELXL (Sheldrick, 2015) for 1_5gpa_144huv. Molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa; Olex2 (Dolomanov et al., 2009) for 1_5gpa_144huv. Software used to prepare material for publication: SHELXL 2014/7 (Sheldrick, 2015) for 0minUV, 140minUV, 270minUV, 530minUV, 660minUV, 790minUV, 920minUV, 1050minUV, 1290minUV, 1950minUV, 0minUV_01GPa, 0minUV_075GPa, 10hUV_075GPa, 44hUV_075GPa, 44hUV_01MPa, 0minUV_1GPa, 140minUV_1GPa, 270minUV_1GPa, 400minUV_1GPa, 580minUV_1GPa, 760minUV_1GPa, 940minUV_1GPa, 1120minUV_1GPa, 1300minUV_1GPa; Olex2 (Dolomanov et al., 2009) for 1_5gpa_144huv.
C8H12N+·C23H27O3− | Dx = 1.123 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 4608 reflections |
a = 6.2484 (3) Å | θ = 1.6–22.2° |
b = 13.7976 (5) Å | µ = 0.07 mm−1 |
c = 32.4874 (12) Å | T = 299 K |
V = 2800.8 (2) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.12 × 0.10 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 5414 independent reflections |
Radiation source: fine-focus sealed tube | 3235 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −17→14 |
Tmin = 0.921, Tmax = 1.000 | l = −40→39 |
25399 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.062 | H-atom parameters constrained |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0489P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
5414 reflections | Δρmax = 0.12 e Å−3 |
324 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.8 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.0310 (6) | 0.2437 (2) | 0.62912 (9) | 0.0820 (11) | |
O2 | 0.6173 (4) | 0.63153 (17) | 0.51657 (8) | 0.0518 (7) | |
O3 | 0.3168 (5) | 0.6207 (2) | 0.55225 (8) | 0.0634 (8) | |
N1 | 0.0337 (5) | 0.6701 (2) | 0.49106 (8) | 0.0439 (8) | |
H1A | 0.1341 | 0.6488 | 0.5083 | 0.053* | |
H1B | −0.0948 | 0.6531 | 0.5004 | 0.053* | |
H1C | 0.0411 | 0.7344 | 0.4892 | 0.053* | |
C1 | 0.8135 (6) | 0.2762 (3) | 0.68701 (10) | 0.0402 (9) | |
C2 | 0.8888 (6) | 0.3406 (3) | 0.71687 (12) | 0.0461 (10) | |
C3 | 0.8311 (7) | 0.3242 (3) | 0.75783 (12) | 0.0495 (10) | |
H3 | 0.8794 | 0.3669 | 0.7779 | 0.059* | |
C4 | 0.7050 (6) | 0.2470 (3) | 0.76942 (11) | 0.0475 (10) | |
C5 | 0.6316 (6) | 0.1855 (3) | 0.73881 (11) | 0.0472 (10) | |
H5 | 0.5441 | 0.1338 | 0.7462 | 0.057* | |
C6 | 0.6834 (6) | 0.1981 (2) | 0.69771 (11) | 0.0409 (9) | |
C7 | 0.8843 (7) | 0.2910 (3) | 0.64286 (11) | 0.0468 (10) | |
C8 | 0.7773 (6) | 0.3659 (2) | 0.61708 (10) | 0.0377 (9) | |
C9 | 0.8780 (7) | 0.3976 (3) | 0.58169 (11) | 0.0489 (10) | |
H9 | 1.0067 | 0.3696 | 0.5736 | 0.059* | |
C10 | 0.7894 (7) | 0.4702 (3) | 0.55835 (11) | 0.0509 (11) | |
H10 | 0.8602 | 0.4916 | 0.5349 | 0.061* | |
C11 | 0.5965 (6) | 0.5120 (2) | 0.56925 (11) | 0.0389 (9) | |
C12 | 0.4919 (7) | 0.4779 (3) | 0.60349 (12) | 0.0542 (11) | |
H12 | 0.3590 | 0.5032 | 0.6106 | 0.065* | |
C13 | 0.5829 (7) | 0.4061 (3) | 0.62750 (12) | 0.0551 (11) | |
H13 | 0.5120 | 0.3847 | 0.6510 | 0.066* | |
C14 | 0.5027 (7) | 0.5943 (3) | 0.54432 (12) | 0.0454 (10) | |
C15 | 1.0303 (7) | 0.4257 (3) | 0.70584 (12) | 0.0570 (12) | |
H15 | 1.0504 | 0.4252 | 0.6759 | 0.068* | |
C16 | 1.2499 (7) | 0.4164 (3) | 0.72572 (14) | 0.0713 (13) | |
H16A | 1.3103 | 0.3544 | 0.7190 | 0.107* | |
H16B | 1.2360 | 0.4219 | 0.7551 | 0.107* | |
H16C | 1.3417 | 0.4669 | 0.7157 | 0.107* | |
C17 | 0.9255 (8) | 0.5224 (3) | 0.71743 (18) | 0.0974 (18) | |
H17A | 0.9084 | 0.5257 | 0.7468 | 0.146* | |
H17B | 0.7879 | 0.5271 | 0.7044 | 0.146* | |
H17C | 1.0146 | 0.5749 | 0.7084 | 0.146* | |
C18 | 0.6424 (8) | 0.2263 (4) | 0.81398 (12) | 0.0659 (13) | |
H18 | 0.6455 | 0.1555 | 0.8165 | 0.079* | |
C19 | 0.7978 (9) | 0.2619 (4) | 0.84530 (14) | 0.103 (2) | |
H19A | 0.8030 | 0.3314 | 0.8445 | 0.155* | |
H19B | 0.9372 | 0.2361 | 0.8394 | 0.155* | |
H19C | 0.7533 | 0.2410 | 0.8722 | 0.155* | |
C20 | 0.4171 (9) | 0.2539 (5) | 0.82246 (16) | 0.108 (2) | |
H20A | 0.3270 | 0.2306 | 0.8007 | 0.162* | |
H20B | 0.4062 | 0.3232 | 0.8241 | 0.162* | |
H20C | 0.3724 | 0.2259 | 0.8481 | 0.162* | |
C21 | 0.6044 (7) | 0.1270 (3) | 0.66513 (12) | 0.0558 (12) | |
H21 | 0.5881 | 0.1632 | 0.6394 | 0.067* | |
C22 | 0.7685 (9) | 0.0474 (3) | 0.65759 (15) | 0.0792 (15) | |
H22A | 0.7881 | 0.0105 | 0.6824 | 0.119* | |
H22B | 0.9023 | 0.0760 | 0.6496 | 0.119* | |
H22C | 0.7187 | 0.0055 | 0.6360 | 0.119* | |
C23 | 0.3890 (8) | 0.0825 (4) | 0.67528 (14) | 0.0815 (15) | |
H23A | 0.2879 | 0.1330 | 0.6812 | 0.122* | |
H23B | 0.4031 | 0.0410 | 0.6989 | 0.122* | |
H23C | 0.3394 | 0.0453 | 0.6522 | 0.122* | |
C24 | 0.2781 (8) | 0.6620 (3) | 0.43207 (13) | 0.0658 (13) | |
H24A | 0.3923 | 0.6441 | 0.4503 | 0.099* | |
H24B | 0.2736 | 0.7313 | 0.4294 | 0.099* | |
H24C | 0.3019 | 0.6334 | 0.4055 | 0.099* | |
C25 | 0.0684 (7) | 0.6263 (3) | 0.44928 (11) | 0.0497 (11) | |
H25 | −0.0456 | 0.6504 | 0.4312 | 0.060* | |
C26 | 0.0456 (7) | 0.5176 (3) | 0.45174 (11) | 0.0496 (11) | |
C27 | −0.1409 (8) | 0.4731 (3) | 0.43944 (13) | 0.0693 (13) | |
H27 | −0.2546 | 0.5107 | 0.4301 | 0.083* | |
C28 | −0.1618 (11) | 0.3731 (4) | 0.44078 (17) | 0.0918 (19) | |
H28 | −0.2884 | 0.3442 | 0.4322 | 0.110* | |
C29 | 0.0010 (15) | 0.3178 (4) | 0.45456 (18) | 0.101 (2) | |
H29 | −0.0142 | 0.2508 | 0.4556 | 0.121* | |
C30 | 0.1882 (12) | 0.3598 (4) | 0.46706 (16) | 0.0931 (18) | |
H30 | 0.3005 | 0.3214 | 0.4764 | 0.112* | |
C31 | 0.2104 (8) | 0.4601 (3) | 0.46584 (13) | 0.0683 (13) | |
H31 | 0.3375 | 0.4885 | 0.4746 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.100 (3) | 0.084 (2) | 0.061 (2) | 0.051 (2) | 0.0339 (19) | 0.0261 (17) |
O2 | 0.0509 (17) | 0.0491 (15) | 0.0555 (16) | 0.0022 (14) | 0.0013 (15) | 0.0209 (13) |
O3 | 0.0474 (19) | 0.086 (2) | 0.0564 (18) | 0.0215 (17) | 0.0051 (16) | 0.0227 (15) |
N1 | 0.045 (2) | 0.0415 (17) | 0.0453 (19) | 0.0014 (15) | −0.0010 (16) | 0.0094 (15) |
C1 | 0.046 (2) | 0.039 (2) | 0.036 (2) | 0.0121 (19) | 0.003 (2) | 0.0074 (18) |
C2 | 0.051 (3) | 0.042 (2) | 0.045 (2) | 0.002 (2) | 0.002 (2) | 0.0060 (19) |
C3 | 0.056 (3) | 0.052 (2) | 0.041 (2) | 0.000 (2) | 0.002 (2) | −0.0038 (19) |
C4 | 0.049 (3) | 0.057 (3) | 0.037 (2) | 0.005 (2) | 0.004 (2) | 0.005 (2) |
C5 | 0.053 (3) | 0.047 (2) | 0.042 (2) | −0.001 (2) | 0.001 (2) | 0.0119 (19) |
C6 | 0.046 (2) | 0.040 (2) | 0.037 (2) | 0.005 (2) | −0.003 (2) | 0.0095 (17) |
C7 | 0.057 (3) | 0.040 (2) | 0.043 (2) | 0.006 (2) | 0.006 (2) | 0.0064 (18) |
C8 | 0.044 (2) | 0.036 (2) | 0.032 (2) | 0.0041 (18) | 0.0029 (18) | 0.0038 (16) |
C9 | 0.050 (3) | 0.051 (2) | 0.046 (2) | 0.013 (2) | 0.015 (2) | 0.0113 (19) |
C10 | 0.053 (3) | 0.055 (2) | 0.045 (2) | 0.008 (2) | 0.012 (2) | 0.021 (2) |
C11 | 0.040 (2) | 0.039 (2) | 0.038 (2) | 0.0002 (19) | −0.0048 (19) | 0.0063 (17) |
C12 | 0.045 (3) | 0.065 (3) | 0.053 (2) | 0.009 (2) | 0.014 (2) | 0.018 (2) |
C13 | 0.056 (3) | 0.064 (3) | 0.045 (2) | 0.010 (2) | 0.014 (2) | 0.022 (2) |
C14 | 0.047 (3) | 0.047 (2) | 0.042 (2) | 0.001 (2) | −0.006 (2) | 0.005 (2) |
C15 | 0.064 (3) | 0.054 (3) | 0.054 (3) | −0.009 (2) | 0.002 (2) | 0.004 (2) |
C16 | 0.064 (3) | 0.074 (3) | 0.075 (3) | −0.002 (3) | 0.010 (3) | −0.001 (3) |
C17 | 0.074 (3) | 0.049 (3) | 0.169 (6) | −0.001 (3) | 0.011 (4) | 0.009 (3) |
C18 | 0.068 (3) | 0.089 (3) | 0.041 (3) | 0.002 (3) | 0.012 (3) | 0.000 (2) |
C19 | 0.100 (4) | 0.168 (6) | 0.042 (3) | −0.014 (4) | 0.000 (3) | 0.000 (3) |
C20 | 0.091 (5) | 0.163 (6) | 0.070 (4) | 0.004 (4) | 0.033 (3) | −0.001 (4) |
C21 | 0.071 (3) | 0.052 (2) | 0.044 (2) | −0.004 (3) | −0.010 (2) | 0.002 (2) |
C22 | 0.099 (4) | 0.063 (3) | 0.075 (3) | 0.008 (3) | −0.004 (3) | −0.019 (3) |
C23 | 0.077 (4) | 0.087 (3) | 0.081 (3) | −0.024 (3) | −0.012 (3) | −0.001 (3) |
C24 | 0.080 (4) | 0.068 (3) | 0.049 (2) | −0.010 (3) | 0.018 (2) | −0.001 (2) |
C25 | 0.055 (3) | 0.054 (2) | 0.039 (2) | −0.001 (2) | −0.007 (2) | 0.0066 (19) |
C26 | 0.059 (3) | 0.055 (3) | 0.035 (2) | −0.002 (2) | 0.001 (2) | −0.0023 (19) |
C27 | 0.071 (4) | 0.080 (3) | 0.057 (3) | −0.017 (3) | 0.007 (3) | −0.014 (3) |
C28 | 0.112 (5) | 0.085 (4) | 0.079 (4) | −0.042 (4) | 0.025 (4) | −0.028 (3) |
C29 | 0.158 (7) | 0.060 (4) | 0.084 (4) | −0.022 (5) | 0.040 (5) | −0.009 (3) |
C30 | 0.130 (6) | 0.063 (4) | 0.086 (4) | 0.016 (4) | 0.019 (4) | 0.003 (3) |
C31 | 0.076 (4) | 0.057 (3) | 0.072 (3) | −0.002 (3) | −0.001 (3) | 0.000 (2) |
O1—C7 | 1.210 (4) | C17—H17B | 0.9600 |
O2—C14 | 1.261 (4) | C17—H17C | 0.9600 |
O3—C14 | 1.244 (5) | C18—C20 | 1.484 (7) |
N1—C25 | 1.502 (4) | C18—C19 | 1.489 (6) |
N1—H1A | 0.8900 | C18—H18 | 0.9800 |
N1—H1B | 0.8900 | C19—H19A | 0.9600 |
N1—H1C | 0.8900 | C19—H19B | 0.9600 |
C1—C6 | 1.395 (5) | C19—H19C | 0.9600 |
C1—C2 | 1.396 (5) | C20—H20A | 0.9600 |
C1—C7 | 1.514 (5) | C20—H20B | 0.9600 |
C2—C3 | 1.397 (5) | C20—H20C | 0.9600 |
C2—C15 | 1.514 (5) | C21—C23 | 1.516 (6) |
C3—C4 | 1.378 (5) | C21—C22 | 1.522 (6) |
C3—H3 | 0.9300 | C21—H21 | 0.9800 |
C4—C5 | 1.385 (5) | C22—H22A | 0.9600 |
C4—C18 | 1.526 (5) | C22—H22B | 0.9600 |
C5—C6 | 1.385 (5) | C22—H22C | 0.9600 |
C5—H5 | 0.9300 | C23—H23A | 0.9600 |
C6—C21 | 1.524 (5) | C23—H23B | 0.9600 |
C7—C8 | 1.489 (5) | C23—H23C | 0.9600 |
C8—C13 | 1.378 (5) | C24—C25 | 1.507 (6) |
C8—C9 | 1.382 (5) | C24—H24A | 0.9600 |
C9—C10 | 1.373 (5) | C24—H24B | 0.9600 |
C9—H9 | 0.9300 | C24—H24C | 0.9600 |
C10—C11 | 1.382 (5) | C25—C26 | 1.510 (5) |
C10—H10 | 0.9300 | C25—H25 | 0.9800 |
C11—C12 | 1.373 (5) | C26—C27 | 1.377 (6) |
C11—C14 | 1.513 (5) | C26—C31 | 1.378 (6) |
C12—C13 | 1.383 (5) | C27—C28 | 1.386 (7) |
C12—H12 | 0.9300 | C27—H27 | 0.9300 |
C13—H13 | 0.9300 | C28—C29 | 1.348 (9) |
C15—C16 | 1.522 (6) | C28—H28 | 0.9300 |
C15—C17 | 1.532 (6) | C29—C30 | 1.368 (8) |
C15—H15 | 0.9800 | C29—H29 | 0.9300 |
C16—H16A | 0.9600 | C30—C31 | 1.391 (7) |
C16—H16B | 0.9600 | C30—H30 | 0.9300 |
C16—H16C | 0.9600 | C31—H31 | 0.9300 |
C17—H17A | 0.9600 | ||
C25—N1—H1A | 109.5 | C20—C18—C19 | 114.0 (4) |
C25—N1—H1B | 109.5 | C20—C18—C4 | 111.8 (4) |
H1A—N1—H1B | 109.5 | C19—C18—C4 | 114.8 (4) |
C25—N1—H1C | 109.5 | C20—C18—H18 | 105.0 |
H1A—N1—H1C | 109.5 | C19—C18—H18 | 105.0 |
H1B—N1—H1C | 109.5 | C4—C18—H18 | 105.0 |
C6—C1—C2 | 121.0 (3) | C18—C19—H19A | 109.5 |
C6—C1—C7 | 120.7 (3) | C18—C19—H19B | 109.5 |
C2—C1—C7 | 118.3 (3) | H19A—C19—H19B | 109.5 |
C1—C2—C3 | 118.2 (3) | C18—C19—H19C | 109.5 |
C1—C2—C15 | 121.7 (3) | H19A—C19—H19C | 109.5 |
C3—C2—C15 | 120.1 (4) | H19B—C19—H19C | 109.5 |
C4—C3—C2 | 122.2 (4) | C18—C20—H20A | 109.5 |
C4—C3—H3 | 118.9 | C18—C20—H20B | 109.5 |
C2—C3—H3 | 118.9 | H20A—C20—H20B | 109.5 |
C3—C4—C5 | 117.8 (3) | C18—C20—H20C | 109.5 |
C3—C4—C18 | 123.4 (4) | H20A—C20—H20C | 109.5 |
C5—C4—C18 | 118.8 (4) | H20B—C20—H20C | 109.5 |
C4—C5—C6 | 122.6 (4) | C23—C21—C22 | 109.9 (4) |
C4—C5—H5 | 118.7 | C23—C21—C6 | 113.4 (4) |
C6—C5—H5 | 118.7 | C22—C21—C6 | 110.9 (3) |
C5—C6—C1 | 118.2 (3) | C23—C21—H21 | 107.4 |
C5—C6—C21 | 120.9 (3) | C22—C21—H21 | 107.4 |
C1—C6—C21 | 120.8 (3) | C6—C21—H21 | 107.4 |
O1—C7—C8 | 120.4 (3) | C21—C22—H22A | 109.5 |
O1—C7—C1 | 119.9 (3) | C21—C22—H22B | 109.5 |
C8—C7—C1 | 119.7 (3) | H22A—C22—H22B | 109.5 |
C13—C8—C9 | 118.6 (3) | C21—C22—H22C | 109.5 |
C13—C8—C7 | 122.5 (3) | H22A—C22—H22C | 109.5 |
C9—C8—C7 | 118.9 (3) | H22B—C22—H22C | 109.5 |
C10—C9—C8 | 120.5 (4) | C21—C23—H23A | 109.5 |
C10—C9—H9 | 119.8 | C21—C23—H23B | 109.5 |
C8—C9—H9 | 119.8 | H23A—C23—H23B | 109.5 |
C9—C10—C11 | 121.0 (3) | C21—C23—H23C | 109.5 |
C9—C10—H10 | 119.5 | H23A—C23—H23C | 109.5 |
C11—C10—H10 | 119.5 | H23B—C23—H23C | 109.5 |
C12—C11—C10 | 118.6 (3) | C25—C24—H24A | 109.5 |
C12—C11—C14 | 120.4 (4) | C25—C24—H24B | 109.5 |
C10—C11—C14 | 120.9 (3) | H24A—C24—H24B | 109.5 |
C11—C12—C13 | 120.5 (4) | C25—C24—H24C | 109.5 |
C11—C12—H12 | 119.8 | H24A—C24—H24C | 109.5 |
C13—C12—H12 | 119.8 | H24B—C24—H24C | 109.5 |
C8—C13—C12 | 120.8 (4) | N1—C25—C24 | 109.2 (3) |
C8—C13—H13 | 119.6 | N1—C25—C26 | 109.8 (3) |
C12—C13—H13 | 119.6 | C24—C25—C26 | 115.2 (4) |
O3—C14—O2 | 124.0 (4) | N1—C25—H25 | 107.4 |
O3—C14—C11 | 118.1 (4) | C24—C25—H25 | 107.4 |
O2—C14—C11 | 117.9 (4) | C26—C25—H25 | 107.4 |
C2—C15—C16 | 111.1 (3) | C27—C26—C31 | 118.2 (4) |
C2—C15—C17 | 111.6 (4) | C27—C26—C25 | 120.5 (4) |
C16—C15—C17 | 110.8 (4) | C31—C26—C25 | 121.3 (4) |
C2—C15—H15 | 107.7 | C26—C27—C28 | 120.9 (5) |
C16—C15—H15 | 107.7 | C26—C27—H27 | 119.5 |
C17—C15—H15 | 107.7 | C28—C27—H27 | 119.5 |
C15—C16—H16A | 109.5 | C29—C28—C27 | 120.2 (6) |
C15—C16—H16B | 109.5 | C29—C28—H28 | 119.9 |
H16A—C16—H16B | 109.5 | C27—C28—H28 | 119.9 |
C15—C16—H16C | 109.5 | C28—C29—C30 | 120.2 (6) |
H16A—C16—H16C | 109.5 | C28—C29—H29 | 119.9 |
H16B—C16—H16C | 109.5 | C30—C29—H29 | 119.9 |
C15—C17—H17A | 109.5 | C29—C30—C31 | 119.9 (6) |
C15—C17—H17B | 109.5 | C29—C30—H30 | 120.0 |
H17A—C17—H17B | 109.5 | C31—C30—H30 | 120.0 |
C15—C17—H17C | 109.5 | C26—C31—C30 | 120.5 (5) |
H17A—C17—H17C | 109.5 | C26—C31—H31 | 119.8 |
H17B—C17—H17C | 109.5 | C30—C31—H31 | 119.8 |
C31H39NO3 | Dx = 1.123 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3644 reflections |
a = 6.2711 (3) Å | θ = 1.6–21.1° |
b = 13.7242 (7) Å | µ = 0.07 mm−1 |
c = 32.5405 (13) Å | T = 299 K |
V = 2800.6 (2) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.12 × 0.10 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 5416 independent reflections |
Radiation source: fine-focus sealed tube | 2804 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.078 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −14→16 |
Tmin = 0.882, Tmax = 1.000 | l = −39→40 |
25271 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0392P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
5416 reflections | Δρmax = 0.13 e Å−3 |
411 parameters | Δρmin = −0.15 e Å−3 |
300 restraints | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.8 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 1.0366 (10) | 0.2455 (4) | 0.63034 (15) | 0.087 (2) | 0.882 (7) |
O2 | 0.6209 (5) | 0.6313 (2) | 0.51675 (10) | 0.0590 (9) | 0.882 (7) |
O3 | 0.3198 (6) | 0.6195 (3) | 0.55168 (9) | 0.0712 (10) | 0.882 (7) |
C1 | 0.8156 (14) | 0.2773 (6) | 0.6880 (2) | 0.049 (2) | 0.882 (7) |
C2 | 0.8830 (19) | 0.3425 (7) | 0.7181 (3) | 0.057 (2) | 0.882 (7) |
C3 | 0.8223 (17) | 0.3265 (8) | 0.7587 (3) | 0.060 (3) | 0.882 (7) |
H3 | 0.8685 | 0.3697 | 0.7788 | 0.072* | 0.882 (7) |
C4 | 0.6963 (17) | 0.2491 (8) | 0.7699 (2) | 0.056 (3) | 0.882 (7) |
C5 | 0.629 (2) | 0.1865 (9) | 0.7393 (2) | 0.056 (2) | 0.882 (7) |
H5 | 0.5431 | 0.1339 | 0.7463 | 0.067* | 0.882 (7) |
C6 | 0.6859 (15) | 0.1989 (6) | 0.6984 (2) | 0.048 (2) | 0.882 (7) |
C7 | 0.8878 (14) | 0.2922 (6) | 0.6441 (2) | 0.063 (2) | 0.882 (7) |
C8 | 0.7793 (13) | 0.3662 (5) | 0.6180 (2) | 0.049 (2) | 0.882 (7) |
C9 | 0.8772 (10) | 0.3958 (4) | 0.58193 (19) | 0.0530 (16) | 0.882 (7) |
H9 | 1.0029 | 0.3660 | 0.5735 | 0.064* | 0.882 (7) |
C10 | 0.7896 (10) | 0.4688 (4) | 0.55864 (18) | 0.0534 (16) | 0.882 (7) |
H10 | 0.8594 | 0.4895 | 0.5350 | 0.064* | 0.882 (7) |
C11 | 0.6000 (11) | 0.5119 (4) | 0.56974 (17) | 0.047 (2) | 0.882 (7) |
C12 | 0.4961 (12) | 0.4805 (5) | 0.6050 (2) | 0.055 (2) | 0.882 (7) |
H12 | 0.3646 | 0.5068 | 0.6122 | 0.066* | 0.882 (7) |
C13 | 0.5898 (12) | 0.4098 (5) | 0.6293 (2) | 0.058 (2) | 0.882 (7) |
H13 | 0.5240 | 0.3914 | 0.6537 | 0.070* | 0.882 (7) |
C14 | 0.5063 (9) | 0.5945 (3) | 0.54446 (14) | 0.0510 (12) | 0.882 (7) |
C15 | 1.0217 (16) | 0.4284 (7) | 0.7071 (4) | 0.067 (3) | 0.882 (7) |
H15 | 1.0354 | 0.4293 | 0.6771 | 0.080* | 0.882 (7) |
C16 | 1.2454 (16) | 0.4171 (8) | 0.7248 (4) | 0.077 (3) | 0.882 (7) |
H16A | 1.3301 | 0.4726 | 0.7173 | 0.116* | 0.882 (7) |
H16B | 1.2371 | 0.4126 | 0.7542 | 0.116* | 0.882 (7) |
H16C | 1.3099 | 0.3591 | 0.7140 | 0.116* | 0.882 (7) |
C17 | 0.9233 (17) | 0.5251 (6) | 0.7199 (3) | 0.098 (3) | 0.882 (7) |
H17A | 1.0169 | 0.5774 | 0.7123 | 0.147* | 0.882 (7) |
H17B | 0.7884 | 0.5333 | 0.7064 | 0.147* | 0.882 (7) |
H17C | 0.9025 | 0.5256 | 0.7491 | 0.147* | 0.882 (7) |
C18 | 0.6349 (17) | 0.2282 (8) | 0.8144 (2) | 0.080 (3) | 0.882 (7) |
H18 | 0.6422 | 0.1571 | 0.8167 | 0.096* | 0.882 (7) |
C19 | 0.7880 (13) | 0.2640 (6) | 0.8460 (2) | 0.101 (3) | 0.882 (7) |
H19A | 0.9303 | 0.2459 | 0.8383 | 0.152* | 0.882 (7) |
H19B | 0.7783 | 0.3337 | 0.8479 | 0.152* | 0.882 (7) |
H19C | 0.7540 | 0.2355 | 0.8721 | 0.152* | 0.882 (7) |
C20 | 0.4083 (12) | 0.2516 (6) | 0.8229 (2) | 0.099 (3) | 0.882 (7) |
H20A | 0.3206 | 0.2261 | 0.8012 | 0.149* | 0.882 (7) |
H20B | 0.3666 | 0.2229 | 0.8486 | 0.149* | 0.882 (7) |
H20C | 0.3909 | 0.3210 | 0.8244 | 0.149* | 0.882 (7) |
C21 | 0.6085 (12) | 0.1281 (5) | 0.66565 (19) | 0.067 (2) | 0.882 (7) |
H21 | 0.5917 | 0.1651 | 0.6401 | 0.080* | 0.882 (7) |
C22 | 0.7733 (12) | 0.0497 (5) | 0.65774 (19) | 0.091 (3) | 0.882 (7) |
H22A | 0.7215 | 0.0059 | 0.6370 | 0.136* | 0.882 (7) |
H22B | 0.9035 | 0.0793 | 0.6485 | 0.136* | 0.882 (7) |
H22C | 0.7995 | 0.0143 | 0.6827 | 0.136* | 0.882 (7) |
C23 | 0.3921 (12) | 0.0815 (5) | 0.6755 (2) | 0.094 (3) | 0.882 (7) |
H23A | 0.2887 | 0.1317 | 0.6804 | 0.140* | 0.882 (7) |
H23B | 0.3470 | 0.0423 | 0.6526 | 0.140* | 0.882 (7) |
H23C | 0.4053 | 0.0413 | 0.6995 | 0.140* | 0.882 (7) |
O1D | 1.094 (6) | 0.286 (3) | 0.6418 (13) | 0.080 (12)* | 0.118 (7) |
O2D | 0.6209 (5) | 0.6313 (2) | 0.51675 (10) | 0.0590 (9) | 0.118 (7) |
O3D | 0.3198 (6) | 0.6195 (3) | 0.55168 (9) | 0.0712 (10) | 0.118 (7) |
C1D | 0.803 (10) | 0.289 (4) | 0.6902 (12) | 0.049 (14)* | 0.118 (7) |
C2D | 0.910 (13) | 0.344 (5) | 0.7192 (15) | 0.047 (14)* | 0.118 (7) |
C3D | 0.866 (12) | 0.321 (5) | 0.7605 (15) | 0.040 (13)* | 0.118 (7) |
H3D | 0.9282 | 0.3576 | 0.7813 | 0.049* | 0.118 (7) |
C4D | 0.728 (11) | 0.242 (5) | 0.7706 (13) | 0.043 (13)* | 0.118 (7) |
C5D | 0.618 (16) | 0.193 (7) | 0.7397 (13) | 0.060 (14)* | 0.118 (7) |
H5D | 0.5176 | 0.1459 | 0.7464 | 0.072* | 0.118 (7) |
C6D | 0.660 (12) | 0.215 (5) | 0.6992 (13) | 0.049 (14)* | 0.118 (7) |
C7D | 0.866 (7) | 0.282 (3) | 0.6436 (12) | 0.061 (14)* | 0.118 (7) |
C8D | 0.776 (7) | 0.370 (3) | 0.6204 (11) | 0.051 (14)* | 0.118 (7) |
C9D | 0.905 (7) | 0.424 (2) | 0.5942 (10) | 0.054 (13)* | 0.118 (7) |
H9D | 1.0504 | 0.4106 | 0.5933 | 0.065* | 0.118 (7) |
C10D | 0.823 (6) | 0.497 (2) | 0.5693 (10) | 0.061 (13)* | 0.118 (7) |
H10D | 0.9121 | 0.5318 | 0.5520 | 0.073* | 0.118 (7) |
C11D | 0.603 (6) | 0.5174 (15) | 0.5704 (7) | 0.048 (14)* | 0.118 (7) |
C12D | 0.479 (7) | 0.463 (3) | 0.5968 (12) | 0.050 (13)* | 0.118 (7) |
H12D | 0.3330 | 0.4754 | 0.5980 | 0.060* | 0.118 (7) |
C13D | 0.560 (7) | 0.390 (3) | 0.6216 (15) | 0.040 (13)* | 0.118 (7) |
H13D | 0.4711 | 0.3549 | 0.6390 | 0.049* | 0.118 (7) |
C14D | 0.5063 (9) | 0.5945 (3) | 0.54446 (14) | 0.0510 (12) | 0.118 (7) |
C15D | 1.058 (11) | 0.426 (4) | 0.708 (2) | 0.055 (14)* | 0.118 (7) |
H15D | 1.1137 | 0.4094 | 0.6810 | 0.066* | 0.118 (7) |
C16D | 1.248 (12) | 0.431 (6) | 0.736 (3) | 0.07 (2)* | 0.118 (7) |
H16D | 1.3372 | 0.4843 | 0.7274 | 0.099* | 0.118 (7) |
H16E | 1.2031 | 0.4399 | 0.7635 | 0.099* | 0.118 (7) |
H16F | 1.3273 | 0.3710 | 0.7334 | 0.099* | 0.118 (7) |
C17D | 0.937 (15) | 0.523 (5) | 0.702 (2) | 0.09 (2)* | 0.118 (7) |
H17D | 0.8172 | 0.5123 | 0.6842 | 0.142* | 0.118 (7) |
H17E | 0.8866 | 0.5460 | 0.7283 | 0.142* | 0.118 (7) |
H17F | 1.0306 | 0.5702 | 0.6902 | 0.142* | 0.118 (7) |
C18D | 0.654 (10) | 0.219 (5) | 0.8157 (13) | 0.064 (14)* | 0.118 (7) |
H18D | 0.5753 | 0.1573 | 0.8154 | 0.076* | 0.118 (7) |
C19D | 0.834 (10) | 0.210 (5) | 0.8464 (18) | 0.099 (14)* | 0.118 (7) |
H19D | 0.9273 | 0.1580 | 0.8383 | 0.149* | 0.118 (7) |
H19E | 0.9123 | 0.2699 | 0.8474 | 0.149* | 0.118 (7) |
H19F | 0.7762 | 0.1961 | 0.8731 | 0.149* | 0.118 (7) |
C20D | 0.498 (10) | 0.301 (4) | 0.8271 (18) | 0.12 (2)* | 0.118 (7) |
H20D | 0.3869 | 0.3047 | 0.8069 | 0.173* | 0.118 (7) |
H20E | 0.4374 | 0.2884 | 0.8536 | 0.173* | 0.118 (7) |
H20F | 0.5736 | 0.3622 | 0.8279 | 0.173* | 0.118 (7) |
C21D | 0.587 (8) | 0.160 (4) | 0.6602 (14) | 0.081 (14)* | 0.118 (7) |
H21D | 0.4634 | 0.1941 | 0.6489 | 0.097* | 0.118 (7) |
C22D | 0.778 (7) | 0.181 (3) | 0.6324 (12) | 0.107 (17)* | 0.118 (7) |
H22D | 0.8874 | 0.1321 | 0.6362 | 0.128* | 0.118 (7) |
H22E | 0.7341 | 0.1804 | 0.6038 | 0.128* | 0.118 (7) |
C23D | 0.523 (12) | 0.056 (4) | 0.668 (2) | 0.14 (2)* | 0.118 (7) |
H23D | 0.4011 | 0.0551 | 0.6857 | 0.213* | 0.118 (7) |
H23E | 0.4867 | 0.0259 | 0.6422 | 0.213* | 0.118 (7) |
H23F | 0.6387 | 0.0219 | 0.6804 | 0.213* | 0.118 (7) |
N1 | 0.0361 (5) | 0.6693 (2) | 0.49147 (9) | 0.0489 (10) | |
H1A | 0.1369 | 0.6477 | 0.5084 | 0.059* | |
H1B | −0.0915 | 0.6528 | 0.5012 | 0.059* | |
H1C | 0.0447 | 0.7339 | 0.4895 | 0.059* | |
C24 | 0.2792 (9) | 0.6599 (4) | 0.43248 (15) | 0.0773 (17) | |
H24A | 0.3917 | 0.6437 | 0.4513 | 0.116* | |
H24B | 0.2744 | 0.7292 | 0.4288 | 0.116* | |
H24C | 0.3053 | 0.6289 | 0.4065 | 0.116* | |
C25 | 0.0671 (8) | 0.6247 (3) | 0.44975 (13) | 0.0563 (13) | |
H25 | −0.0462 | 0.6494 | 0.4318 | 0.068* | |
C26 | 0.0433 (9) | 0.5164 (4) | 0.45214 (14) | 0.0577 (14) | |
C27 | −0.1433 (10) | 0.4726 (4) | 0.43978 (15) | 0.0780 (17) | |
H27 | −0.2555 | 0.5110 | 0.4305 | 0.094* | |
C28 | −0.1667 (14) | 0.3726 (6) | 0.4410 (2) | 0.109 (3) | |
H28 | −0.2936 | 0.3440 | 0.4324 | 0.130* | |
C29 | −0.0051 (18) | 0.3166 (6) | 0.4546 (2) | 0.122 (3) | |
H29 | −0.0214 | 0.2493 | 0.4553 | 0.146* | |
C30 | 0.1813 (15) | 0.3570 (5) | 0.4672 (2) | 0.109 (2) | |
H30 | 0.2923 | 0.3177 | 0.4763 | 0.130* | |
C31 | 0.2052 (11) | 0.4583 (4) | 0.46630 (16) | 0.0831 (18) | |
H31 | 0.3317 | 0.4863 | 0.4754 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.104 (4) | 0.085 (4) | 0.071 (3) | 0.049 (4) | 0.036 (3) | 0.025 (3) |
O2 | 0.057 (2) | 0.060 (2) | 0.0600 (19) | 0.0005 (18) | 0.0036 (18) | 0.0233 (17) |
O3 | 0.055 (2) | 0.100 (3) | 0.059 (2) | 0.023 (2) | 0.003 (2) | 0.0250 (19) |
C1 | 0.056 (4) | 0.044 (4) | 0.047 (4) | 0.016 (3) | 0.002 (3) | 0.013 (3) |
C2 | 0.061 (5) | 0.049 (4) | 0.059 (4) | 0.005 (3) | 0.004 (4) | 0.012 (3) |
C3 | 0.064 (7) | 0.058 (4) | 0.057 (4) | 0.001 (5) | −0.004 (4) | −0.002 (3) |
C4 | 0.056 (5) | 0.065 (5) | 0.046 (4) | 0.008 (4) | 0.005 (3) | 0.010 (3) |
C5 | 0.062 (4) | 0.055 (4) | 0.051 (4) | 0.000 (4) | 0.000 (3) | 0.013 (3) |
C6 | 0.051 (4) | 0.045 (4) | 0.047 (4) | 0.009 (4) | −0.007 (3) | 0.010 (3) |
C7 | 0.075 (5) | 0.057 (4) | 0.056 (4) | 0.005 (4) | 0.005 (4) | 0.011 (3) |
C8 | 0.059 (4) | 0.048 (4) | 0.039 (3) | 0.007 (3) | 0.006 (3) | 0.010 (3) |
C9 | 0.054 (4) | 0.054 (4) | 0.051 (4) | 0.009 (3) | 0.011 (3) | 0.003 (3) |
C10 | 0.060 (4) | 0.056 (4) | 0.045 (3) | 0.007 (3) | 0.005 (3) | 0.013 (3) |
C11 | 0.050 (4) | 0.045 (3) | 0.045 (3) | 0.004 (3) | −0.005 (3) | 0.009 (2) |
C12 | 0.052 (4) | 0.067 (4) | 0.046 (4) | 0.005 (3) | 0.008 (3) | 0.014 (4) |
C13 | 0.061 (5) | 0.072 (5) | 0.043 (4) | 0.007 (4) | 0.010 (4) | 0.020 (4) |
C14 | 0.054 (3) | 0.055 (3) | 0.044 (3) | 0.002 (3) | −0.007 (3) | 0.005 (2) |
C15 | 0.068 (6) | 0.068 (5) | 0.065 (4) | −0.006 (4) | −0.005 (4) | 0.008 (3) |
C16 | 0.074 (5) | 0.084 (6) | 0.074 (8) | −0.003 (4) | 0.007 (5) | −0.008 (5) |
C17 | 0.076 (5) | 0.059 (4) | 0.159 (10) | −0.003 (4) | 0.010 (7) | 0.005 (6) |
C18 | 0.082 (6) | 0.105 (6) | 0.052 (4) | 0.010 (5) | 0.011 (4) | −0.005 (4) |
C19 | 0.103 (6) | 0.150 (8) | 0.051 (4) | 0.005 (6) | −0.002 (4) | −0.002 (5) |
C20 | 0.091 (6) | 0.138 (7) | 0.070 (5) | −0.014 (6) | 0.033 (4) | −0.009 (4) |
C21 | 0.092 (6) | 0.057 (4) | 0.050 (4) | −0.008 (4) | −0.014 (4) | 0.008 (3) |
C22 | 0.126 (7) | 0.080 (5) | 0.067 (4) | 0.017 (5) | −0.001 (4) | −0.022 (4) |
C23 | 0.095 (6) | 0.101 (5) | 0.084 (5) | −0.034 (5) | −0.016 (5) | −0.003 (4) |
O2D | 0.057 (2) | 0.060 (2) | 0.0600 (19) | 0.0005 (18) | 0.0036 (18) | 0.0233 (17) |
O3D | 0.055 (2) | 0.100 (3) | 0.059 (2) | 0.023 (2) | 0.003 (2) | 0.0250 (19) |
C14D | 0.054 (3) | 0.055 (3) | 0.044 (3) | 0.002 (3) | −0.007 (3) | 0.005 (2) |
N1 | 0.049 (2) | 0.053 (2) | 0.045 (2) | 0.0009 (18) | 0.000 (2) | 0.0095 (18) |
C24 | 0.097 (5) | 0.086 (4) | 0.050 (3) | −0.006 (3) | 0.020 (3) | −0.002 (3) |
C25 | 0.059 (4) | 0.070 (3) | 0.040 (3) | 0.002 (3) | −0.008 (3) | 0.006 (3) |
C26 | 0.069 (4) | 0.064 (3) | 0.040 (3) | −0.001 (3) | 0.000 (3) | −0.005 (3) |
C27 | 0.080 (5) | 0.089 (5) | 0.065 (4) | −0.011 (4) | 0.002 (3) | −0.014 (3) |
C28 | 0.128 (7) | 0.101 (6) | 0.097 (5) | −0.042 (5) | 0.028 (5) | −0.034 (5) |
C29 | 0.180 (11) | 0.075 (6) | 0.112 (6) | −0.028 (6) | 0.043 (7) | −0.011 (5) |
C30 | 0.145 (8) | 0.075 (5) | 0.106 (5) | 0.016 (5) | 0.007 (5) | 0.002 (4) |
C31 | 0.092 (5) | 0.074 (4) | 0.083 (4) | −0.001 (4) | −0.007 (4) | −0.003 (3) |
O1—C7 | 1.218 (7) | C4D—C18D | 1.57 (2) |
O2—C14 | 1.259 (5) | C5D—C6D | 1.38 (2) |
O3—C14 | 1.241 (5) | C5D—H5D | 0.9300 |
C1—C2 | 1.391 (8) | C6D—C21D | 1.55 (2) |
C1—C6 | 1.391 (7) | C7D—C22D | 1.53 (2) |
C1—C7 | 1.513 (7) | C7D—C8D | 1.53 (2) |
C2—C3 | 1.392 (7) | C8D—C13D | 1.38 (2) |
C2—C15 | 1.508 (8) | C8D—C9D | 1.39 (2) |
C3—C4 | 1.375 (7) | C9D—C10D | 1.39 (2) |
C3—H3 | 0.9300 | C9D—H9D | 0.9300 |
C4—C5 | 1.382 (8) | C10D—C11D | 1.41 (2) |
C4—C18 | 1.526 (8) | C10D—H10D | 0.9300 |
C5—C6 | 1.387 (7) | C11D—C12D | 1.38 (2) |
C5—H5 | 0.9300 | C11D—C14D | 1.48 (2) |
C6—C21 | 1.521 (7) | C12D—C13D | 1.38 (2) |
C7—C8 | 1.489 (7) | C12D—H12D | 0.9300 |
C8—C13 | 1.381 (7) | C13D—H13D | 0.9300 |
C8—C9 | 1.386 (7) | C15D—C16D | 1.49 (3) |
C9—C10 | 1.371 (6) | C15D—C17D | 1.54 (3) |
C9—H9 | 0.9300 | C15D—H15D | 0.9800 |
C10—C11 | 1.376 (7) | C16D—H16D | 0.9600 |
C10—H10 | 0.9300 | C16D—H16E | 0.9600 |
C11—C12 | 1.387 (7) | C16D—H16F | 0.9600 |
C11—C14 | 1.519 (7) | C17D—H17D | 0.9600 |
C12—C13 | 1.383 (7) | C17D—H17E | 0.9600 |
C12—H12 | 0.9300 | C17D—H17F | 0.9600 |
C13—H13 | 0.9300 | C18D—C19D | 1.51 (3) |
C15—C17 | 1.523 (9) | C18D—C20D | 1.54 (3) |
C15—C16 | 1.524 (9) | C18D—H18D | 0.9800 |
C15—H15 | 0.9800 | C19D—H19D | 0.9600 |
C16—H16A | 0.9600 | C19D—H19E | 0.9600 |
C16—H16B | 0.9600 | C19D—H19F | 0.9600 |
C16—H16C | 0.9600 | C20D—H20D | 0.9600 |
C17—H17A | 0.9600 | C20D—H20E | 0.9600 |
C17—H17B | 0.9600 | C20D—H20F | 0.9600 |
C17—H17C | 0.9600 | C21D—C23D | 1.50 (3) |
C18—C20 | 1.483 (10) | C21D—C22D | 1.53 (3) |
C18—C19 | 1.489 (10) | C21D—H21D | 0.9800 |
C18—H18 | 0.9800 | C22D—H22D | 0.9700 |
C19—H19A | 0.9600 | C22D—H22E | 0.9700 |
C19—H19B | 0.9600 | C23D—H23D | 0.9600 |
C19—H19C | 0.9600 | C23D—H23E | 0.9600 |
C20—H20A | 0.9600 | C23D—H23F | 0.9600 |
C20—H20B | 0.9600 | N1—C25 | 1.502 (5) |
C20—H20C | 0.9600 | N1—H1A | 0.8900 |
C21—C22 | 1.513 (9) | N1—H1B | 0.8900 |
C21—C23 | 1.534 (9) | N1—H1C | 0.8900 |
C21—H21 | 0.9800 | C24—C25 | 1.523 (7) |
C22—H22A | 0.9600 | C24—H24A | 0.9600 |
C22—H22B | 0.9600 | C24—H24B | 0.9600 |
C22—H22C | 0.9600 | C24—H24C | 0.9600 |
C23—H23A | 0.9600 | C25—C26 | 1.495 (6) |
C23—H23B | 0.9600 | C25—H25 | 0.9800 |
C23—H23C | 0.9600 | C26—C31 | 1.371 (7) |
O1D—C7D | 1.43 (2) | C26—C27 | 1.375 (7) |
O2D—C14D | 1.259 (5) | C27—C28 | 1.381 (8) |
O3D—C14D | 1.241 (5) | C27—H27 | 0.9300 |
C1D—C2D | 1.38 (2) | C28—C29 | 1.347 (10) |
C1D—C6D | 1.39 (2) | C28—H28 | 0.9300 |
C1D—C7D | 1.57 (2) | C29—C30 | 1.357 (10) |
C2D—C3D | 1.41 (2) | C29—H29 | 0.9300 |
C2D—C15D | 1.51 (2) | C30—C31 | 1.397 (8) |
C3D—C4D | 1.42 (2) | C30—H30 | 0.9300 |
C3D—H3D | 0.9300 | C31—H31 | 0.9300 |
C4D—C5D | 1.39 (2) | ||
C2—C1—C6 | 120.4 (5) | C22D—C7D—C8D | 118 (3) |
C2—C1—C7 | 119.1 (6) | O1D—C7D—C1D | 107 (3) |
C6—C1—C7 | 120.5 (6) | C22D—C7D—C1D | 101 (2) |
C1—C2—C3 | 118.8 (6) | C8D—C7D—C1D | 110 (3) |
C1—C2—C15 | 120.7 (7) | C13D—C8D—C9D | 119 (3) |
C3—C2—C15 | 120.4 (7) | C13D—C8D—C7D | 120 (3) |
C4—C3—C2 | 122.2 (7) | C9D—C8D—C7D | 121 (3) |
C4—C3—H3 | 118.9 | C8D—C9D—C10D | 122 (3) |
C2—C3—H3 | 118.9 | C8D—C9D—H9D | 119.1 |
C3—C4—C5 | 117.6 (6) | C10D—C9D—H9D | 119.1 |
C3—C4—C18 | 122.9 (7) | C9D—C10D—C11D | 120 (3) |
C5—C4—C18 | 119.5 (7) | C9D—C10D—H10D | 120.1 |
C4—C5—C6 | 122.6 (6) | C11D—C10D—H10D | 120.1 |
C4—C5—H5 | 118.7 | C12D—C11D—C10D | 117 (2) |
C6—C5—H5 | 118.7 | C12D—C11D—C14D | 121 (2) |
C5—C6—C1 | 118.5 (6) | C10D—C11D—C14D | 122 (2) |
C5—C6—C21 | 120.8 (6) | C11D—C12D—C13D | 123 (3) |
C1—C6—C21 | 120.8 (5) | C11D—C12D—H12D | 118.4 |
O1—C7—C8 | 119.9 (6) | C13D—C12D—H12D | 118.4 |
O1—C7—C1 | 120.4 (6) | C12D—C13D—C8D | 119 (3) |
C8—C7—C1 | 119.7 (6) | C12D—C13D—H13D | 120.3 |
C13—C8—C9 | 118.6 (5) | C8D—C13D—H13D | 120.3 |
C13—C8—C7 | 122.5 (6) | O3D—C14D—O2D | 124.2 (4) |
C9—C8—C7 | 118.8 (6) | O3D—C14D—C11D | 118.3 (15) |
C10—C9—C8 | 120.3 (5) | O2D—C14D—C11D | 117.5 (15) |
C10—C9—H9 | 119.8 | C16D—C15D—C2D | 113 (4) |
C8—C9—H9 | 119.8 | C16D—C15D—C17D | 116 (4) |
C9—C10—C11 | 121.0 (5) | C2D—C15D—C17D | 112 (4) |
C9—C10—H10 | 119.5 | C16D—C15D—H15D | 105.1 |
C11—C10—H10 | 119.5 | C2D—C15D—H15D | 105.1 |
C10—C11—C12 | 119.3 (5) | C17D—C15D—H15D | 105.1 |
C10—C11—C14 | 120.9 (5) | C15D—C16D—H16D | 109.5 |
C12—C11—C14 | 119.8 (6) | C15D—C16D—H16E | 109.5 |
C13—C12—C11 | 119.4 (6) | H16D—C16D—H16E | 109.5 |
C13—C12—H12 | 120.3 | C15D—C16D—H16F | 109.5 |
C11—C12—H12 | 120.3 | H16D—C16D—H16F | 109.5 |
C8—C13—C12 | 121.2 (6) | H16E—C16D—H16F | 109.5 |
C8—C13—H13 | 119.4 | C15D—C17D—H17D | 109.5 |
C12—C13—H13 | 119.4 | C15D—C17D—H17E | 109.5 |
O3—C14—O2 | 124.2 (4) | H17D—C17D—H17E | 109.5 |
O3—C14—C11 | 118.0 (5) | C15D—C17D—H17F | 109.5 |
O2—C14—C11 | 117.8 (5) | H17D—C17D—H17F | 109.5 |
C2—C15—C17 | 112.5 (7) | H17E—C17D—H17F | 109.5 |
C2—C15—C16 | 111.2 (6) | C19D—C18D—C20D | 112 (4) |
C17—C15—C16 | 110.9 (7) | C19D—C18D—C4D | 115 (3) |
C2—C15—H15 | 107.3 | C20D—C18D—C4D | 105 (3) |
C17—C15—H15 | 107.3 | C19D—C18D—H18D | 108.3 |
C16—C15—H15 | 107.3 | C20D—C18D—H18D | 108.3 |
C15—C16—H16A | 109.5 | C4D—C18D—H18D | 108.3 |
C15—C16—H16B | 109.5 | C18D—C19D—H19D | 109.5 |
H16A—C16—H16B | 109.5 | C18D—C19D—H19E | 109.5 |
C15—C16—H16C | 109.5 | H19D—C19D—H19E | 109.5 |
H16A—C16—H16C | 109.5 | C18D—C19D—H19F | 109.5 |
H16B—C16—H16C | 109.5 | H19D—C19D—H19F | 109.5 |
C15—C17—H17A | 109.5 | H19E—C19D—H19F | 109.5 |
C15—C17—H17B | 109.5 | C18D—C20D—H20D | 109.5 |
H17A—C17—H17B | 109.5 | C18D—C20D—H20E | 109.5 |
C15—C17—H17C | 109.5 | H20D—C20D—H20E | 109.5 |
H17A—C17—H17C | 109.5 | C18D—C20D—H20F | 109.5 |
H17B—C17—H17C | 109.5 | H20D—C20D—H20F | 109.5 |
C20—C18—C19 | 114.7 (7) | H20E—C20D—H20F | 109.5 |
C20—C18—C4 | 112.2 (7) | C23D—C21D—C22D | 120 (4) |
C19—C18—C4 | 115.5 (7) | C23D—C21D—C6D | 114 (3) |
C20—C18—H18 | 104.3 | C22D—C21D—C6D | 99 (2) |
C19—C18—H18 | 104.3 | C23D—C21D—H21D | 107.8 |
C4—C18—H18 | 104.3 | C22D—C21D—H21D | 107.8 |
C18—C19—H19A | 109.5 | C6D—C21D—H21D | 107.8 |
C18—C19—H19B | 109.5 | C7D—C22D—C21D | 108 (2) |
H19A—C19—H19B | 109.5 | C7D—C22D—H22D | 110.0 |
C18—C19—H19C | 109.5 | C21D—C22D—H22D | 110.0 |
H19A—C19—H19C | 109.5 | C7D—C22D—H22E | 110.0 |
H19B—C19—H19C | 109.5 | C21D—C22D—H22E | 110.0 |
C18—C20—H20A | 109.5 | H22D—C22D—H22E | 108.4 |
C18—C20—H20B | 109.5 | C21D—C23D—H23D | 109.5 |
H20A—C20—H20B | 109.5 | C21D—C23D—H23E | 109.5 |
C18—C20—H20C | 109.5 | H23D—C23D—H23E | 109.5 |
H20A—C20—H20C | 109.5 | C21D—C23D—H23F | 109.5 |
H20B—C20—H20C | 109.5 | H23D—C23D—H23F | 109.5 |
C22—C21—C6 | 110.8 (6) | H23E—C23D—H23F | 109.5 |
C22—C21—C23 | 110.1 (6) | C25—N1—H1A | 109.5 |
C6—C21—C23 | 113.7 (6) | C25—N1—H1B | 109.5 |
C22—C21—H21 | 107.3 | H1A—N1—H1B | 109.5 |
C6—C21—H21 | 107.3 | C25—N1—H1C | 109.5 |
C23—C21—H21 | 107.3 | H1A—N1—H1C | 109.5 |
C21—C22—H22A | 109.5 | H1B—N1—H1C | 109.5 |
C21—C22—H22B | 109.5 | C25—C24—H24A | 109.5 |
H22A—C22—H22B | 109.5 | C25—C24—H24B | 109.5 |
C21—C22—H22C | 109.5 | H24A—C24—H24B | 109.5 |
H22A—C22—H22C | 109.5 | C25—C24—H24C | 109.5 |
H22B—C22—H22C | 109.5 | H24A—C24—H24C | 109.5 |
C21—C23—H23A | 109.5 | H24B—C24—H24C | 109.5 |
C21—C23—H23B | 109.5 | C26—C25—N1 | 110.2 (4) |
H23A—C23—H23B | 109.5 | C26—C25—C24 | 114.9 (4) |
C21—C23—H23C | 109.5 | N1—C25—C24 | 108.5 (4) |
H23A—C23—H23C | 109.5 | C26—C25—H25 | 107.7 |
H23B—C23—H23C | 109.5 | N1—C25—H25 | 107.7 |
C2D—C1D—C6D | 125 (3) | C24—C25—H25 | 107.7 |
C2D—C1D—C7D | 125 (3) | C31—C26—C27 | 118.3 (5) |
C6D—C1D—C7D | 108 (2) | C31—C26—C25 | 121.5 (5) |
C1D—C2D—C3D | 116 (3) | C27—C26—C25 | 120.3 (5) |
C1D—C2D—C15D | 123 (3) | C26—C27—C28 | 121.1 (7) |
C3D—C2D—C15D | 121 (3) | C26—C27—H27 | 119.4 |
C2D—C3D—C4D | 120 (3) | C28—C27—H27 | 119.4 |
C2D—C3D—H3D | 119.8 | C29—C28—C27 | 119.8 (8) |
C4D—C3D—H3D | 119.8 | C29—C28—H28 | 120.1 |
C5D—C4D—C3D | 120 (3) | C27—C28—H28 | 120.1 |
C5D—C4D—C18D | 116 (3) | C28—C29—C30 | 120.9 (8) |
C3D—C4D—C18D | 123 (3) | C28—C29—H29 | 119.5 |
C6D—C5D—C4D | 120 (3) | C30—C29—H29 | 119.5 |
C6D—C5D—H5D | 120.2 | C29—C30—C31 | 119.5 (8) |
C4D—C5D—H5D | 120.2 | C29—C30—H30 | 120.2 |
C5D—C6D—C1D | 119 (3) | C31—C30—H30 | 120.2 |
C5D—C6D—C21D | 129 (3) | C26—C31—C30 | 120.4 (7) |
C1D—C6D—C21D | 112 (2) | C26—C31—H31 | 119.8 |
O1D—C7D—C22D | 113 (3) | C30—C31—H31 | 119.8 |
O1D—C7D—C8D | 108 (3) |
C31H39NO3 | Dx = 1.121 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 2672 reflections |
a = 6.2975 (5) Å | θ = 1.6–19.9° |
b = 13.6726 (12) Å | µ = 0.07 mm−1 |
c = 32.5998 (19) Å | T = 299 K |
V = 2806.9 (4) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.12 × 0.10 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 5431 independent reflections |
Radiation source: fine-focus sealed tube | 2313 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.104 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −16→14 |
Tmin = 0.783, Tmax = 1.000 | l = −39→40 |
25077 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.077 | H-atom parameters constrained |
wR(F2) = 0.171 | w = 1/[σ2(Fo2) + (0.0388P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
5431 reflections | Δρmax = 0.14 e Å−3 |
505 parameters | Δρmin = −0.14 e Å−3 |
571 restraints | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.9 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 1.0391 (18) | 0.2455 (7) | 0.6316 (3) | 0.089 (3) | 0.721 (4) |
O2 | 0.6264 (7) | 0.6312 (3) | 0.51689 (13) | 0.0704 (13) | 0.721 (4) |
O3 | 0.3267 (8) | 0.6187 (4) | 0.55118 (13) | 0.0830 (15) | 0.721 (4) |
C1 | 0.817 (3) | 0.2771 (10) | 0.6886 (4) | 0.059 (4) | 0.721 (4) |
C2 | 0.883 (4) | 0.3431 (13) | 0.7188 (5) | 0.067 (4) | 0.721 (4) |
C3 | 0.821 (4) | 0.3291 (16) | 0.7595 (5) | 0.069 (4) | 0.721 (4) |
H3 | 0.8676 | 0.3724 | 0.7795 | 0.083* | 0.721 (4) |
C4 | 0.692 (4) | 0.2526 (16) | 0.7705 (4) | 0.062 (4) | 0.721 (4) |
C5 | 0.627 (5) | 0.1879 (19) | 0.7401 (4) | 0.070 (4) | 0.721 (4) |
H5 | 0.5410 | 0.1353 | 0.7471 | 0.084* | 0.721 (4) |
C6 | 0.688 (4) | 0.1999 (12) | 0.6992 (4) | 0.062 (4) | 0.721 (4) |
C7 | 0.893 (2) | 0.2940 (9) | 0.6457 (4) | 0.066 (4) | 0.721 (4) |
C8 | 0.785 (2) | 0.3672 (10) | 0.6188 (4) | 0.052 (4) | 0.721 (4) |
C9 | 0.881 (2) | 0.3932 (8) | 0.5820 (4) | 0.060 (3) | 0.721 (4) |
H9 | 1.0043 | 0.3619 | 0.5735 | 0.072* | 0.721 (4) |
C10 | 0.7923 (19) | 0.4654 (8) | 0.5583 (3) | 0.058 (3) | 0.721 (4) |
H10 | 0.8605 | 0.4842 | 0.5342 | 0.070* | 0.721 (4) |
C11 | 0.608 (2) | 0.5100 (10) | 0.5689 (4) | 0.049 (3) | 0.721 (4) |
C12 | 0.503 (2) | 0.4796 (11) | 0.6049 (4) | 0.061 (4) | 0.721 (4) |
H12 | 0.3714 | 0.5058 | 0.6119 | 0.073* | 0.721 (4) |
C13 | 0.598 (2) | 0.4106 (8) | 0.6298 (4) | 0.057 (4) | 0.721 (4) |
H13 | 0.5332 | 0.3932 | 0.6544 | 0.069* | 0.721 (4) |
C14 | 0.5131 (13) | 0.5941 (5) | 0.54453 (19) | 0.0617 (18) | 0.721 (4) |
C15 | 1.020 (3) | 0.4314 (11) | 0.7089 (7) | 0.078 (4) | 0.721 (4) |
H15 | 1.0294 | 0.4354 | 0.6789 | 0.093* | 0.721 (4) |
C16 | 1.245 (3) | 0.4183 (19) | 0.7247 (7) | 0.085 (6) | 0.721 (4) |
H16A | 1.3014 | 0.3573 | 0.7149 | 0.127* | 0.721 (4) |
H16B | 1.3324 | 0.4711 | 0.7150 | 0.127* | 0.721 (4) |
H16C | 1.2442 | 0.4182 | 0.7541 | 0.127* | 0.721 (4) |
C17 | 0.925 (3) | 0.5269 (10) | 0.7236 (5) | 0.099 (5) | 0.721 (4) |
H17A | 1.0180 | 0.5800 | 0.7165 | 0.149* | 0.721 (4) |
H17B | 0.7894 | 0.5367 | 0.7108 | 0.149* | 0.721 (4) |
H17C | 0.9072 | 0.5247 | 0.7528 | 0.149* | 0.721 (4) |
C18 | 0.634 (3) | 0.2298 (16) | 0.8151 (4) | 0.092 (5) | 0.721 (4) |
H18 | 0.6460 | 0.1585 | 0.8170 | 0.111* | 0.721 (4) |
C19 | 0.783 (2) | 0.2664 (13) | 0.8464 (4) | 0.101 (5) | 0.721 (4) |
H19A | 0.9258 | 0.2508 | 0.8384 | 0.152* | 0.721 (4) |
H19B | 0.7684 | 0.3360 | 0.8490 | 0.152* | 0.721 (4) |
H19C | 0.7524 | 0.2360 | 0.8723 | 0.152* | 0.721 (4) |
C20 | 0.405 (2) | 0.2493 (16) | 0.8240 (4) | 0.094 (5) | 0.721 (4) |
H20A | 0.3193 | 0.2233 | 0.8022 | 0.142* | 0.721 (4) |
H20B | 0.3663 | 0.2186 | 0.8494 | 0.142* | 0.721 (4) |
H20C | 0.3823 | 0.3186 | 0.8260 | 0.142* | 0.721 (4) |
C21 | 0.611 (2) | 0.1297 (10) | 0.6663 (4) | 0.076 (4) | 0.721 (4) |
H21 | 0.5920 | 0.1677 | 0.6411 | 0.091* | 0.721 (4) |
C22 | 0.775 (2) | 0.0522 (11) | 0.6575 (5) | 0.097 (5) | 0.721 (4) |
H22A | 0.7223 | 0.0088 | 0.6367 | 0.145* | 0.721 (4) |
H22B | 0.9034 | 0.0825 | 0.6482 | 0.145* | 0.721 (4) |
H22C | 0.8031 | 0.0157 | 0.6821 | 0.145* | 0.721 (4) |
C23 | 0.393 (2) | 0.0810 (10) | 0.6764 (4) | 0.103 (5) | 0.721 (4) |
H23A | 0.2897 | 0.1308 | 0.6820 | 0.154* | 0.721 (4) |
H23B | 0.3474 | 0.0424 | 0.6535 | 0.154* | 0.721 (4) |
H23C | 0.4084 | 0.0397 | 0.7001 | 0.154* | 0.721 (4) |
O1D | 1.090 (6) | 0.278 (3) | 0.6392 (15) | 0.081 (11)* | 0.201 (4) |
O2D | 0.6264 (7) | 0.6312 (3) | 0.51689 (13) | 0.0704 (13) | 0.201 (4) |
O3D | 0.3267 (8) | 0.6187 (4) | 0.55118 (13) | 0.0830 (15) | 0.201 (4) |
C1D | 0.799 (9) | 0.287 (3) | 0.6895 (11) | 0.063 (12)* | 0.201 (4) |
C2D | 0.897 (12) | 0.344 (4) | 0.7186 (14) | 0.063 (12)* | 0.201 (4) |
C3D | 0.852 (12) | 0.323 (5) | 0.7599 (14) | 0.065 (12)* | 0.201 (4) |
H3D | 0.9105 | 0.3617 | 0.7805 | 0.078* | 0.201 (4) |
C4D | 0.718 (10) | 0.243 (5) | 0.7706 (12) | 0.050 (11)* | 0.201 (4) |
C5D | 0.615 (15) | 0.191 (6) | 0.7397 (12) | 0.073 (12)* | 0.201 (4) |
H5D | 0.5177 | 0.1424 | 0.7464 | 0.087* | 0.201 (4) |
C6D | 0.659 (11) | 0.212 (4) | 0.6992 (12) | 0.065 (12)* | 0.201 (4) |
C7D | 0.863 (6) | 0.277 (2) | 0.6434 (11) | 0.071 (12)* | 0.201 (4) |
C8D | 0.767 (7) | 0.361 (3) | 0.6182 (13) | 0.054 (11)* | 0.201 (4) |
C9D | 0.892 (7) | 0.412 (3) | 0.5906 (13) | 0.056 (11)* | 0.201 (4) |
H9D | 1.0326 | 0.3928 | 0.5872 | 0.067* | 0.201 (4) |
C10D | 0.816 (6) | 0.490 (3) | 0.5679 (12) | 0.056 (11)* | 0.201 (4) |
H10D | 0.9054 | 0.5224 | 0.5497 | 0.067* | 0.201 (4) |
C11D | 0.605 (7) | 0.520 (3) | 0.5726 (13) | 0.054 (11)* | 0.201 (4) |
C12D | 0.481 (8) | 0.468 (3) | 0.6005 (14) | 0.063 (12)* | 0.201 (4) |
H12D | 0.3406 | 0.4863 | 0.6041 | 0.075* | 0.201 (4) |
C13D | 0.559 (6) | 0.390 (3) | 0.6231 (13) | 0.044 (11)* | 0.201 (4) |
H13D | 0.4705 | 0.3568 | 0.6414 | 0.053* | 0.201 (4) |
C14D | 0.5131 (13) | 0.5941 (5) | 0.54453 (19) | 0.0617 (18) | 0.201 (4) |
C15D | 1.051 (9) | 0.425 (4) | 0.708 (2) | 0.070 (11)* | 0.201 (4) |
H15D | 1.1014 | 0.4108 | 0.6800 | 0.084* | 0.201 (4) |
C16D | 1.242 (12) | 0.422 (7) | 0.735 (3) | 0.09 (2)* | 0.201 (4) |
H16D | 1.3366 | 0.4745 | 0.7273 | 0.140* | 0.201 (4) |
H16E | 1.1992 | 0.4306 | 0.7629 | 0.140* | 0.201 (4) |
H16F | 1.3134 | 0.3608 | 0.7317 | 0.140* | 0.201 (4) |
C17D | 0.935 (12) | 0.524 (4) | 0.706 (2) | 0.081 (18)* | 0.201 (4) |
H17D | 0.8153 | 0.5183 | 0.6877 | 0.121* | 0.201 (4) |
H17E | 0.8881 | 0.5418 | 0.7326 | 0.121* | 0.201 (4) |
H17F | 1.0309 | 0.5726 | 0.6954 | 0.121* | 0.201 (4) |
C18D | 0.648 (8) | 0.220 (5) | 0.8160 (12) | 0.082 (11)* | 0.201 (4) |
H18D | 0.5815 | 0.1552 | 0.8160 | 0.099* | 0.201 (4) |
C19D | 0.826 (8) | 0.218 (3) | 0.8469 (15) | 0.097 (13)* | 0.201 (4) |
H19D | 0.9295 | 0.1702 | 0.8389 | 0.145* | 0.201 (4) |
H19E | 0.8925 | 0.2815 | 0.8480 | 0.145* | 0.201 (4) |
H19F | 0.7707 | 0.2022 | 0.8735 | 0.145* | 0.201 (4) |
C20D | 0.474 (8) | 0.296 (4) | 0.8263 (16) | 0.122 (19)* | 0.201 (4) |
H20D | 0.3652 | 0.2934 | 0.8057 | 0.184* | 0.201 (4) |
H20E | 0.4134 | 0.2804 | 0.8526 | 0.184* | 0.201 (4) |
H20F | 0.5353 | 0.3598 | 0.8271 | 0.184* | 0.201 (4) |
C21D | 0.585 (7) | 0.156 (3) | 0.6603 (12) | 0.097 (12)* | 0.201 (4) |
H21D | 0.4603 | 0.1884 | 0.6486 | 0.116* | 0.201 (4) |
C22D | 0.779 (6) | 0.175 (2) | 0.6334 (10) | 0.106 (13)* | 0.201 (4) |
H22D | 0.8873 | 0.1268 | 0.6386 | 0.127* | 0.201 (4) |
H22E | 0.7392 | 0.1719 | 0.6046 | 0.127* | 0.201 (4) |
C23D | 0.531 (10) | 0.051 (3) | 0.6700 (18) | 0.15 (2)* | 0.201 (4) |
H23D | 0.4071 | 0.0484 | 0.6871 | 0.224* | 0.201 (4) |
H23E | 0.5045 | 0.0158 | 0.6450 | 0.224* | 0.201 (4) |
H23F | 0.6483 | 0.0208 | 0.6842 | 0.224* | 0.201 (4) |
O1P | 1.115 (9) | 0.303 (5) | 0.650 (2) | 0.083 (13)* | 0.078 (4) |
O2P | 0.6264 (7) | 0.6312 (3) | 0.51689 (13) | 0.0704 (13) | 0.078 (4) |
O3P | 0.3267 (8) | 0.6187 (4) | 0.55118 (13) | 0.0830 (15) | 0.078 (4) |
C1P | 0.803 (14) | 0.293 (5) | 0.6970 (16) | 0.061 (13)* | 0.078 (4) |
C2P | 0.846 (17) | 0.350 (6) | 0.7311 (16) | 0.065 (14)* | 0.078 (4) |
C3P | 0.779 (18) | 0.321 (7) | 0.7697 (17) | 0.064 (13)* | 0.078 (4) |
H3P | 0.8091 | 0.3590 | 0.7926 | 0.077* | 0.078 (4) |
C4P | 0.67 (2) | 0.235 (7) | 0.774 (2) | 0.047 (13)* | 0.078 (4) |
C5P | 0.62 (3) | 0.176 (8) | 0.740 (2) | 0.070 (13)* | 0.078 (4) |
H5P | 0.5476 | 0.1183 | 0.7429 | 0.084* | 0.078 (4) |
C6P | 0.70 (2) | 0.205 (7) | 0.702 (2) | 0.064 (13)* | 0.078 (4) |
C7P | 0.938 (8) | 0.350 (3) | 0.6675 (12) | 0.064 (13)* | 0.078 (4) |
C8P | 0.834 (7) | 0.413 (2) | 0.6345 (11) | 0.045 (12)* | 0.078 (4) |
C9P | 0.943 (7) | 0.448 (3) | 0.6006 (13) | 0.060 (13)* | 0.078 (4) |
H9P | 1.0855 | 0.4319 | 0.5974 | 0.072* | 0.078 (4) |
C10P | 0.842 (7) | 0.506 (3) | 0.5713 (13) | 0.059 (13)* | 0.078 (4) |
H10P | 0.9179 | 0.5284 | 0.5487 | 0.071* | 0.078 (4) |
C11P | 0.629 (6) | 0.5307 (12) | 0.5758 (9) | 0.054 (13)* | 0.078 (4) |
C12P | 0.519 (8) | 0.497 (3) | 0.6097 (13) | 0.059 (13)* | 0.078 (4) |
H12P | 0.3761 | 0.5127 | 0.6131 | 0.071* | 0.078 (4) |
C13P | 0.620 (8) | 0.439 (4) | 0.6388 (14) | 0.044 (14)* | 0.078 (4) |
H13P | 0.5446 | 0.4164 | 0.6614 | 0.053* | 0.078 (4) |
C14P | 0.5131 (13) | 0.5941 (5) | 0.54453 (19) | 0.0617 (18) | 0.078 (4) |
C15P | 0.982 (12) | 0.421 (4) | 0.7078 (15) | 0.075 (13)* | 0.078 (4) |
C16P | 1.217 (13) | 0.428 (11) | 0.717 (4) | 0.09 (3)* | 0.078 (4) |
H16G | 1.2809 | 0.4769 | 0.6997 | 0.128* | 0.078 (4) |
H16H | 1.2368 | 0.4466 | 0.7453 | 0.128* | 0.078 (4) |
H16I | 1.2832 | 0.3662 | 0.7121 | 0.128* | 0.078 (4) |
C17P | 0.88 (2) | 0.523 (4) | 0.704 (4) | 0.09 (3)* | 0.078 (4) |
H17G | 0.9791 | 0.5645 | 0.6884 | 0.129* | 0.078 (4) |
H17H | 0.7515 | 0.5182 | 0.6892 | 0.129* | 0.078 (4) |
H17I | 0.8609 | 0.5502 | 0.7303 | 0.129* | 0.078 (4) |
C18P | 0.568 (15) | 0.207 (7) | 0.815 (2) | 0.088 (14)* | 0.078 (4) |
H18P | 0.5541 | 0.1360 | 0.8176 | 0.106* | 0.078 (4) |
C19P | 0.699 (18) | 0.248 (12) | 0.850 (3) | 0.099 (15)* | 0.078 (4) |
H19G | 0.6344 | 0.2297 | 0.8760 | 0.149* | 0.078 (4) |
H19H | 0.8400 | 0.2214 | 0.8491 | 0.149* | 0.078 (4) |
H19I | 0.7050 | 0.3177 | 0.8484 | 0.149* | 0.078 (4) |
C20P | 0.349 (15) | 0.255 (14) | 0.813 (4) | 0.08 (2)* | 0.078 (4) |
H20G | 0.2731 | 0.2415 | 0.8379 | 0.113* | 0.078 (4) |
H20H | 0.3652 | 0.3240 | 0.8096 | 0.113* | 0.078 (4) |
H20I | 0.2724 | 0.2283 | 0.7901 | 0.113* | 0.078 (4) |
C21P | 0.679 (15) | 0.140 (6) | 0.664 (2) | 0.083 (14)* | 0.078 (4) |
H21P | 0.6948 | 0.1837 | 0.6405 | 0.100* | 0.078 (4) |
C22P | 0.863 (17) | 0.068 (11) | 0.661 (5) | 0.10 (3)* | 0.078 (4) |
H22F | 0.8462 | 0.0286 | 0.6371 | 0.147* | 0.078 (4) |
H22G | 0.9940 | 0.1035 | 0.6597 | 0.147* | 0.078 (4) |
H22H | 0.8634 | 0.0270 | 0.6851 | 0.147* | 0.078 (4) |
C23P | 0.463 (15) | 0.093 (9) | 0.659 (4) | 0.11 (3)* | 0.078 (4) |
H23G | 0.4627 | 0.0526 | 0.6351 | 0.168* | 0.078 (4) |
H23H | 0.4339 | 0.0529 | 0.6829 | 0.168* | 0.078 (4) |
H23I | 0.3568 | 0.1425 | 0.6569 | 0.168* | 0.078 (4) |
N1 | 0.0407 (8) | 0.6681 (3) | 0.49166 (13) | 0.0588 (14) | |
H1A | 0.1439 | 0.6476 | 0.5082 | 0.071* | |
H1B | −0.0844 | 0.6499 | 0.5018 | 0.071* | |
H1C | 0.0453 | 0.7330 | 0.4897 | 0.071* | |
C24 | 0.2820 (12) | 0.6581 (5) | 0.4326 (2) | 0.090 (2) | |
H24A | 0.3940 | 0.6412 | 0.4513 | 0.135* | |
H24B | 0.2790 | 0.7277 | 0.4289 | 0.135* | |
H24C | 0.3067 | 0.6268 | 0.4067 | 0.135* | |
C25 | 0.0698 (11) | 0.6239 (5) | 0.45005 (18) | 0.0667 (19) | |
H25 | −0.0428 | 0.6494 | 0.4323 | 0.080* | |
C26 | 0.0434 (13) | 0.5159 (6) | 0.45254 (19) | 0.068 (2) | |
C27 | −0.1423 (15) | 0.4729 (7) | 0.4402 (2) | 0.092 (3) | |
H27 | −0.2530 | 0.5122 | 0.4310 | 0.111* | |
C28 | −0.170 (2) | 0.3712 (9) | 0.4409 (3) | 0.125 (4) | |
H28 | −0.2967 | 0.3430 | 0.4322 | 0.150* | |
C29 | −0.008 (3) | 0.3147 (9) | 0.4547 (4) | 0.147 (6) | |
H29 | −0.0244 | 0.2471 | 0.4551 | 0.176* | |
C30 | 0.176 (2) | 0.3542 (8) | 0.4678 (3) | 0.133 (4) | |
H30 | 0.2837 | 0.3140 | 0.4775 | 0.160* | |
C31 | 0.2042 (15) | 0.4560 (6) | 0.4668 (2) | 0.095 (3) | |
H31 | 0.3314 | 0.4832 | 0.4757 | 0.114* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.111 (7) | 0.083 (7) | 0.075 (6) | 0.041 (6) | 0.037 (6) | 0.022 (5) |
O2 | 0.073 (3) | 0.075 (3) | 0.063 (3) | 0.001 (3) | 0.006 (3) | 0.025 (2) |
O3 | 0.071 (4) | 0.114 (4) | 0.064 (3) | 0.028 (3) | 0.002 (3) | 0.028 (3) |
C1 | 0.068 (7) | 0.052 (6) | 0.058 (6) | 0.019 (6) | 0.001 (6) | 0.016 (5) |
C2 | 0.073 (9) | 0.055 (6) | 0.072 (7) | 0.009 (6) | 0.008 (6) | 0.020 (6) |
C3 | 0.067 (10) | 0.069 (7) | 0.071 (7) | −0.004 (7) | −0.011 (6) | −0.007 (6) |
C4 | 0.055 (9) | 0.071 (9) | 0.061 (7) | 0.009 (7) | 0.007 (6) | 0.012 (6) |
C5 | 0.074 (8) | 0.074 (7) | 0.063 (6) | −0.010 (7) | −0.005 (6) | 0.021 (5) |
C6 | 0.078 (9) | 0.057 (7) | 0.053 (6) | 0.005 (7) | −0.014 (6) | 0.020 (5) |
C7 | 0.088 (9) | 0.056 (6) | 0.055 (6) | 0.004 (7) | 0.001 (6) | 0.009 (5) |
C8 | 0.061 (7) | 0.050 (6) | 0.047 (6) | 0.004 (5) | 0.002 (5) | 0.010 (4) |
C9 | 0.071 (7) | 0.053 (6) | 0.057 (7) | 0.016 (6) | 0.012 (6) | 0.003 (6) |
C10 | 0.064 (7) | 0.059 (7) | 0.051 (6) | 0.006 (6) | 0.008 (5) | 0.002 (6) |
C11 | 0.056 (7) | 0.053 (6) | 0.038 (5) | −0.002 (5) | 0.000 (5) | 0.001 (5) |
C12 | 0.048 (6) | 0.075 (7) | 0.059 (7) | 0.005 (6) | 0.006 (6) | 0.011 (6) |
C13 | 0.066 (8) | 0.066 (8) | 0.040 (6) | −0.011 (7) | 0.004 (6) | 0.004 (6) |
C14 | 0.078 (5) | 0.062 (4) | 0.046 (4) | 0.015 (4) | −0.014 (4) | 0.005 (3) |
C15 | 0.073 (10) | 0.080 (8) | 0.079 (7) | 0.003 (7) | −0.011 (7) | 0.003 (6) |
C16 | 0.088 (10) | 0.088 (10) | 0.079 (14) | −0.003 (7) | 0.010 (9) | −0.001 (9) |
C17 | 0.088 (10) | 0.074 (8) | 0.136 (15) | −0.014 (7) | 0.008 (12) | 0.008 (9) |
C18 | 0.087 (9) | 0.128 (11) | 0.061 (7) | −0.001 (8) | 0.018 (7) | −0.012 (6) |
C19 | 0.106 (11) | 0.135 (12) | 0.063 (7) | −0.001 (10) | 0.000 (7) | −0.002 (8) |
C20 | 0.096 (11) | 0.119 (11) | 0.069 (9) | −0.020 (11) | 0.018 (8) | −0.005 (9) |
C21 | 0.103 (10) | 0.078 (8) | 0.048 (6) | −0.009 (8) | −0.020 (6) | 0.006 (6) |
C22 | 0.125 (12) | 0.099 (9) | 0.067 (7) | 0.024 (11) | −0.009 (9) | −0.016 (6) |
C23 | 0.112 (11) | 0.116 (9) | 0.080 (8) | −0.045 (10) | −0.010 (8) | 0.000 (7) |
O2D | 0.073 (3) | 0.075 (3) | 0.063 (3) | 0.001 (3) | 0.006 (3) | 0.025 (2) |
O3D | 0.071 (4) | 0.114 (4) | 0.064 (3) | 0.028 (3) | 0.002 (3) | 0.028 (3) |
C14D | 0.078 (5) | 0.062 (4) | 0.046 (4) | 0.015 (4) | −0.014 (4) | 0.005 (3) |
O2P | 0.073 (3) | 0.075 (3) | 0.063 (3) | 0.001 (3) | 0.006 (3) | 0.025 (2) |
O3P | 0.071 (4) | 0.114 (4) | 0.064 (3) | 0.028 (3) | 0.002 (3) | 0.028 (3) |
C14P | 0.078 (5) | 0.062 (4) | 0.046 (4) | 0.015 (4) | −0.014 (4) | 0.005 (3) |
N1 | 0.064 (4) | 0.065 (3) | 0.047 (3) | 0.002 (3) | −0.001 (3) | 0.010 (3) |
C24 | 0.106 (7) | 0.107 (6) | 0.057 (4) | −0.012 (5) | 0.023 (5) | 0.001 (4) |
C25 | 0.075 (5) | 0.081 (5) | 0.045 (4) | 0.002 (4) | −0.010 (4) | 0.003 (4) |
C26 | 0.078 (6) | 0.080 (5) | 0.047 (4) | −0.002 (5) | 0.004 (4) | −0.005 (4) |
C27 | 0.098 (7) | 0.106 (7) | 0.073 (5) | −0.011 (6) | 0.008 (5) | −0.018 (5) |
C28 | 0.143 (11) | 0.123 (10) | 0.109 (8) | −0.039 (8) | 0.027 (8) | −0.034 (7) |
C29 | 0.215 (18) | 0.097 (9) | 0.128 (10) | −0.031 (10) | 0.042 (11) | −0.024 (7) |
C30 | 0.187 (13) | 0.087 (8) | 0.125 (9) | 0.013 (8) | 0.007 (9) | 0.003 (6) |
C31 | 0.108 (8) | 0.084 (6) | 0.092 (6) | 0.000 (6) | −0.010 (6) | −0.007 (5) |
O1—C7 | 1.223 (12) | C18D—C20D | 1.54 (3) |
O2—C14 | 1.256 (7) | C18D—H18D | 0.9800 |
O3—C14 | 1.241 (8) | C19D—H19D | 0.9600 |
C1—C6 | 1.376 (12) | C19D—H19E | 0.9600 |
C1—C2 | 1.397 (12) | C19D—H19F | 0.9600 |
C1—C7 | 1.497 (12) | C20D—H20D | 0.9600 |
C2—C3 | 1.398 (13) | C20D—H20E | 0.9600 |
C2—C15 | 1.518 (13) | C20D—H20F | 0.9600 |
C3—C4 | 1.369 (12) | C21D—C23D | 1.51 (3) |
C3—H3 | 0.9300 | C21D—C22D | 1.53 (3) |
C4—C5 | 1.391 (14) | C21D—H21D | 0.9800 |
C4—C18 | 1.534 (13) | C22D—H22D | 0.9700 |
C5—C6 | 1.396 (12) | C22D—H22E | 0.9700 |
C5—H5 | 0.9300 | C23D—H23D | 0.9600 |
C6—C21 | 1.519 (12) | C23D—H23E | 0.9600 |
C7—C8 | 1.494 (11) | C23D—H23F | 0.9600 |
C8—C13 | 1.367 (12) | O1P—C7P | 1.40 (2) |
C8—C9 | 1.391 (11) | O2P—C14P | 1.256 (7) |
C9—C10 | 1.372 (10) | O3P—C14P | 1.241 (8) |
C9—H9 | 0.9300 | C1P—C2P | 1.39 (3) |
C10—C11 | 1.355 (12) | C1P—C6P | 1.39 (2) |
C10—H10 | 0.9300 | C1P—C7P | 1.50 (2) |
C11—C12 | 1.412 (11) | C2P—C3P | 1.39 (2) |
C11—C14 | 1.520 (10) | C2P—C15P | 1.50 (2) |
C12—C13 | 1.380 (11) | C3P—C4P | 1.38 (3) |
C12—H12 | 0.9300 | C3P—H3P | 0.9300 |
C13—H13 | 0.9300 | C4P—C5P | 1.40 (3) |
C15—C17 | 1.516 (15) | C4P—C18P | 1.52 (3) |
C15—C16 | 1.518 (14) | C5P—C6P | 1.39 (3) |
C15—H15 | 0.9800 | C5P—H5P | 0.9300 |
C16—H16A | 0.9600 | C6P—C21P | 1.51 (3) |
C16—H16B | 0.9600 | C7P—C8P | 1.53 (2) |
C16—H16C | 0.9600 | C7P—C15P | 1.66 (2) |
C17—H17A | 0.9600 | C8P—C9P | 1.38 (2) |
C17—H17B | 0.9600 | C8P—C13P | 1.39 (3) |
C17—H17C | 0.9600 | C9P—C10P | 1.40 (2) |
C18—C19 | 1.476 (15) | C9P—H9P | 0.9300 |
C18—C20 | 1.492 (15) | C10P—C11P | 1.39 (3) |
C18—H18 | 0.9800 | C10P—H10P | 0.9300 |
C19—H19A | 0.9600 | C11P—C12P | 1.39 (3) |
C19—H19B | 0.9600 | C11P—C14P | 1.52 (2) |
C19—H19C | 0.9600 | C12P—C13P | 1.39 (3) |
C20—H20A | 0.9600 | C12P—H12P | 0.9300 |
C20—H20B | 0.9600 | C13P—H13P | 0.9300 |
C20—H20C | 0.9600 | C15P—C16P | 1.51 (3) |
C21—C22 | 1.507 (14) | C15P—C17P | 1.53 (3) |
C21—C23 | 1.560 (14) | C16P—H16G | 0.9600 |
C21—H21 | 0.9800 | C16P—H16H | 0.9600 |
C22—H22A | 0.9600 | C16P—H16I | 0.9600 |
C22—H22B | 0.9600 | C17P—H17G | 0.9600 |
C22—H22C | 0.9600 | C17P—H17H | 0.9600 |
C23—H23A | 0.9600 | C17P—H17I | 0.9600 |
C23—H23B | 0.9600 | C18P—C20P | 1.52 (3) |
C23—H23C | 0.9600 | C18P—C19P | 1.52 (3) |
O1D—C7D | 1.44 (2) | C18P—H18P | 0.9800 |
O2D—C14D | 1.256 (7) | C19P—H19G | 0.9600 |
O3D—C14D | 1.241 (8) | C19P—H19H | 0.9600 |
C1D—C2D | 1.37 (2) | C19P—H19I | 0.9600 |
C1D—C6D | 1.39 (2) | C20P—H20G | 0.9600 |
C1D—C7D | 1.56 (2) | C20P—H20H | 0.9600 |
C2D—C3D | 1.41 (2) | C20P—H20I | 0.9600 |
C2D—C15D | 1.51 (2) | C21P—C23P | 1.51 (3) |
C3D—C4D | 1.42 (2) | C21P—C22P | 1.52 (3) |
C3D—H3D | 0.9300 | C21P—H21P | 0.9800 |
C4D—C5D | 1.40 (2) | C22P—H22F | 0.9600 |
C4D—C18D | 1.58 (2) | C22P—H22G | 0.9600 |
C5D—C6D | 1.38 (2) | C22P—H22H | 0.9600 |
C5D—H5D | 0.9300 | C23P—H23G | 0.9600 |
C6D—C21D | 1.55 (2) | C23P—H23H | 0.9600 |
C7D—C22D | 1.52 (2) | C23P—H23I | 0.9600 |
C7D—C8D | 1.53 (2) | N1—C25 | 1.496 (7) |
C8D—C13D | 1.38 (2) | N1—H1A | 0.8900 |
C8D—C9D | 1.38 (2) | N1—H1B | 0.8900 |
C9D—C10D | 1.38 (2) | N1—H1C | 0.8900 |
C9D—H9D | 0.9300 | C24—C25 | 1.525 (9) |
C10D—C11D | 1.40 (2) | C24—H24A | 0.9600 |
C10D—H10D | 0.9300 | C24—H24B | 0.9600 |
C11D—C12D | 1.39 (2) | C24—H24C | 0.9600 |
C11D—C14D | 1.48 (2) | C25—C26 | 1.489 (9) |
C12D—C13D | 1.39 (2) | C25—H25 | 0.9800 |
C12D—H12D | 0.9300 | C26—C27 | 1.370 (10) |
C13D—H13D | 0.9300 | C26—C31 | 1.382 (10) |
C15D—C16D | 1.49 (3) | C27—C28 | 1.402 (11) |
C15D—C17D | 1.54 (3) | C27—H27 | 0.9300 |
C15D—H15D | 0.9800 | C28—C29 | 1.355 (15) |
C16D—H16D | 0.9600 | C28—H28 | 0.9300 |
C16D—H16E | 0.9600 | C29—C30 | 1.347 (14) |
C16D—H16F | 0.9600 | C29—H29 | 0.9300 |
C17D—H17D | 0.9600 | C30—C31 | 1.404 (11) |
C17D—H17E | 0.9600 | C30—H30 | 0.9300 |
C17D—H17F | 0.9600 | C31—H31 | 0.9300 |
C18D—C19D | 1.51 (3) | ||
C6—C1—C2 | 119.6 (10) | C18D—C19D—H19D | 109.5 |
C6—C1—C7 | 122.7 (10) | C18D—C19D—H19E | 109.5 |
C2—C1—C7 | 117.6 (11) | H19D—C19D—H19E | 109.5 |
C1—C2—C3 | 119.7 (11) | C18D—C19D—H19F | 109.5 |
C1—C2—C15 | 122.2 (12) | H19D—C19D—H19F | 109.5 |
C3—C2—C15 | 118.1 (12) | H19E—C19D—H19F | 109.5 |
C4—C3—C2 | 121.3 (11) | C18D—C20D—H20D | 109.5 |
C4—C3—H3 | 119.4 | C18D—C20D—H20E | 109.5 |
C2—C3—H3 | 119.4 | H20D—C20D—H20E | 109.5 |
C3—C4—C5 | 118.3 (11) | C18D—C20D—H20F | 109.5 |
C3—C4—C18 | 123.0 (13) | H20D—C20D—H20F | 109.5 |
C5—C4—C18 | 118.4 (12) | H20E—C20D—H20F | 109.5 |
C4—C5—C6 | 121.6 (11) | C23D—C21D—C22D | 118 (4) |
C4—C5—H5 | 119.2 | C23D—C21D—C6D | 111 (3) |
C6—C5—H5 | 119.2 | C22D—C21D—C6D | 98 (2) |
C1—C6—C5 | 119.5 (11) | C23D—C21D—H21D | 109.6 |
C1—C6—C21 | 119.8 (10) | C22D—C21D—H21D | 109.6 |
C5—C6—C21 | 120.7 (11) | C6D—C21D—H21D | 109.6 |
O1—C7—C8 | 119.1 (10) | C7D—C22D—C21D | 108 (2) |
O1—C7—C1 | 120.4 (10) | C7D—C22D—H22D | 110.0 |
C8—C7—C1 | 120.4 (11) | C21D—C22D—H22D | 110.0 |
C13—C8—C9 | 119.3 (9) | C7D—C22D—H22E | 110.0 |
C13—C8—C7 | 122.1 (10) | C21D—C22D—H22E | 110.0 |
C9—C8—C7 | 118.6 (10) | H22D—C22D—H22E | 108.4 |
C10—C9—C8 | 119.6 (10) | C21D—C23D—H23D | 109.5 |
C10—C9—H9 | 120.2 | C21D—C23D—H23E | 109.5 |
C8—C9—H9 | 120.2 | H23D—C23D—H23E | 109.5 |
C11—C10—C9 | 121.8 (9) | C21D—C23D—H23F | 109.5 |
C11—C10—H10 | 119.1 | H23D—C23D—H23F | 109.5 |
C9—C10—H10 | 119.1 | H23E—C23D—H23F | 109.5 |
C10—C11—C12 | 118.9 (9) | C2P—C1P—C6P | 120 (3) |
C10—C11—C14 | 122.9 (9) | C2P—C1P—C7P | 96 (2) |
C12—C11—C14 | 118.1 (10) | C6P—C1P—C7P | 143 (3) |
C13—C12—C11 | 119.1 (11) | C1P—C2P—C3P | 120 (3) |
C13—C12—H12 | 120.5 | C1P—C2P—C15P | 94 (2) |
C11—C12—H12 | 120.5 | C3P—C2P—C15P | 145 (4) |
C8—C13—C12 | 121.1 (10) | C4P—C3P—C2P | 120 (3) |
C8—C13—H13 | 119.4 | C4P—C3P—H3P | 120.1 |
C12—C13—H13 | 119.4 | C2P—C3P—H3P | 120.1 |
O3—C14—O2 | 123.6 (6) | C3P—C4P—C5P | 120 (3) |
O3—C14—C11 | 119.1 (8) | C3P—C4P—C18P | 121 (3) |
O2—C14—C11 | 117.1 (8) | C5P—C4P—C18P | 119 (3) |
C17—C15—C2 | 113.1 (13) | C6P—C5P—C4P | 120 (3) |
C17—C15—C16 | 111.3 (13) | C6P—C5P—H5P | 120.0 |
C2—C15—C16 | 111.4 (12) | C4P—C5P—H5P | 120.0 |
C17—C15—H15 | 106.9 | C5P—C6P—C1P | 120 (3) |
C2—C15—H15 | 106.9 | C5P—C6P—C21P | 123 (3) |
C16—C15—H15 | 106.9 | C1P—C6P—C21P | 117 (3) |
C15—C16—H16A | 109.5 | O1P—C7P—C1P | 118 (3) |
C15—C16—H16B | 109.5 | O1P—C7P—C8P | 109 (3) |
H16A—C16—H16B | 109.5 | C1P—C7P—C8P | 120 (3) |
C15—C16—H16C | 109.5 | O1P—C7P—C15P | 117 (3) |
H16A—C16—H16C | 109.5 | C1P—C7P—C15P | 84 (2) |
H16B—C16—H16C | 109.5 | C8P—C7P—C15P | 107 (2) |
C15—C17—H17A | 109.5 | C9P—C8P—C13P | 118 (3) |
C15—C17—H17B | 109.5 | C9P—C8P—C7P | 123 (3) |
H17A—C17—H17B | 109.5 | C13P—C8P—C7P | 119 (3) |
C15—C17—H17C | 109.5 | C8P—C9P—C10P | 121 (3) |
H17A—C17—H17C | 109.5 | C8P—C9P—H9P | 119.5 |
H17B—C17—H17C | 109.5 | C10P—C9P—H9P | 119.5 |
C19—C18—C20 | 114.9 (12) | C11P—C10P—C9P | 120 (3) |
C19—C18—C4 | 115.7 (13) | C11P—C10P—H10P | 119.8 |
C20—C18—C4 | 112.3 (12) | C9P—C10P—H10P | 119.8 |
C19—C18—H18 | 104.0 | C10P—C11P—C12P | 119 (3) |
C20—C18—H18 | 104.0 | C10P—C11P—C14P | 122 (3) |
C4—C18—H18 | 104.0 | C12P—C11P—C14P | 119 (3) |
C18—C19—H19A | 109.5 | C11P—C12P—C13P | 120 (3) |
C18—C19—H19B | 109.5 | C11P—C12P—H12P | 119.9 |
H19A—C19—H19B | 109.5 | C13P—C12P—H12P | 119.9 |
C18—C19—H19C | 109.5 | C12P—C13P—C8P | 121 (3) |
H19A—C19—H19C | 109.5 | C12P—C13P—H13P | 119.4 |
H19B—C19—H19C | 109.5 | C8P—C13P—H13P | 119.4 |
C18—C20—H20A | 109.5 | O3P—C14P—O2P | 123.6 (6) |
C18—C20—H20B | 109.5 | O3P—C14P—C11P | 119.5 (18) |
H20A—C20—H20B | 109.5 | O2P—C14P—C11P | 115.8 (18) |
C18—C20—H20C | 109.5 | C2P—C15P—C16P | 120 (4) |
H20A—C20—H20C | 109.5 | C2P—C15P—C17P | 114 (4) |
H20B—C20—H20C | 109.5 | C16P—C15P—C17P | 111 (3) |
C22—C21—C6 | 111.0 (12) | C2P—C15P—C7P | 86 (2) |
C22—C21—C23 | 110.0 (10) | C16P—C15P—C7P | 111 (4) |
C6—C21—C23 | 113.8 (10) | C17P—C15P—C7P | 114 (4) |
C22—C21—H21 | 107.3 | C15P—C16P—H16G | 109.5 |
C6—C21—H21 | 107.3 | C15P—C16P—H16H | 109.5 |
C23—C21—H21 | 107.3 | H16G—C16P—H16H | 109.5 |
C21—C22—H22A | 109.5 | C15P—C16P—H16I | 109.5 |
C21—C22—H22B | 109.5 | H16G—C16P—H16I | 109.5 |
H22A—C22—H22B | 109.5 | H16H—C16P—H16I | 109.5 |
C21—C22—H22C | 109.5 | C15P—C17P—H17G | 109.5 |
H22A—C22—H22C | 109.5 | C15P—C17P—H17H | 109.5 |
H22B—C22—H22C | 109.5 | H17G—C17P—H17H | 109.5 |
C21—C23—H23A | 109.5 | C15P—C17P—H17I | 109.5 |
C21—C23—H23B | 109.5 | H17G—C17P—H17I | 109.5 |
H23A—C23—H23B | 109.5 | H17H—C17P—H17I | 109.5 |
C21—C23—H23C | 109.5 | C4P—C18P—C20P | 103 (4) |
H23A—C23—H23C | 109.5 | C4P—C18P—C19P | 111 (4) |
H23B—C23—H23C | 109.5 | C20P—C18P—C19P | 112 (4) |
C2D—C1D—C6D | 123 (3) | C4P—C18P—H18P | 110.4 |
C2D—C1D—C7D | 127 (3) | C20P—C18P—H18P | 110.4 |
C6D—C1D—C7D | 109 (2) | C19P—C18P—H18P | 110.4 |
C1D—C2D—C3D | 117 (3) | C18P—C19P—H19G | 109.5 |
C1D—C2D—C15D | 123 (3) | C18P—C19P—H19H | 109.5 |
C3D—C2D—C15D | 120 (3) | H19G—C19P—H19H | 109.5 |
C2D—C3D—C4D | 121 (3) | C18P—C19P—H19I | 109.5 |
C2D—C3D—H3D | 119.6 | H19G—C19P—H19I | 109.5 |
C4D—C3D—H3D | 119.6 | H19H—C19P—H19I | 109.5 |
C5D—C4D—C3D | 119 (3) | C18P—C20P—H20G | 109.5 |
C5D—C4D—C18D | 116 (3) | C18P—C20P—H20H | 109.5 |
C3D—C4D—C18D | 123 (3) | H20G—C20P—H20H | 109.5 |
C6D—C5D—C4D | 120 (3) | C18P—C20P—H20I | 109.5 |
C6D—C5D—H5D | 120.2 | H20G—C20P—H20I | 109.5 |
C4D—C5D—H5D | 120.2 | H20H—C20P—H20I | 109.5 |
C5D—C6D—C1D | 120 (3) | C6P—C21P—C23P | 113 (4) |
C5D—C6D—C21D | 128 (3) | C6P—C21P—C22P | 112 (4) |
C1D—C6D—C21D | 112 (2) | C23P—C21P—C22P | 114 (4) |
O1D—C7D—C22D | 109 (3) | C6P—C21P—H21P | 105.7 |
O1D—C7D—C8D | 110 (3) | C23P—C21P—H21P | 105.7 |
C22D—C7D—C8D | 115 (3) | C22P—C21P—H21P | 105.7 |
O1D—C7D—C1D | 110 (3) | C21P—C22P—H22F | 109.5 |
C22D—C7D—C1D | 101 (2) | C21P—C22P—H22G | 109.5 |
C8D—C7D—C1D | 110 (3) | H22F—C22P—H22G | 109.5 |
C13D—C8D—C9D | 118 (2) | C21P—C22P—H22H | 109.5 |
C13D—C8D—C7D | 122 (3) | H22F—C22P—H22H | 109.5 |
C9D—C8D—C7D | 120 (3) | H22G—C22P—H22H | 109.5 |
C10D—C9D—C8D | 123 (3) | C21P—C23P—H23G | 109.5 |
C10D—C9D—H9D | 118.7 | C21P—C23P—H23H | 109.5 |
C8D—C9D—H9D | 118.7 | H23G—C23P—H23H | 109.5 |
C9D—C10D—C11D | 120 (3) | C21P—C23P—H23I | 109.5 |
C9D—C10D—H10D | 120.2 | H23G—C23P—H23I | 109.5 |
C11D—C10D—H10D | 120.2 | H23H—C23P—H23I | 109.5 |
C12D—C11D—C10D | 117 (2) | C25—N1—H1A | 109.5 |
C12D—C11D—C14D | 122 (3) | C25—N1—H1B | 109.5 |
C10D—C11D—C14D | 120 (3) | H1A—N1—H1B | 109.5 |
C13D—C12D—C11D | 123 (3) | C25—N1—H1C | 109.5 |
C13D—C12D—H12D | 118.5 | H1A—N1—H1C | 109.5 |
C11D—C12D—H12D | 118.5 | H1B—N1—H1C | 109.5 |
C8D—C13D—C12D | 120 (3) | C25—C24—H24A | 109.5 |
C8D—C13D—H13D | 120.2 | C25—C24—H24B | 109.5 |
C12D—C13D—H13D | 120.2 | H24A—C24—H24B | 109.5 |
O3D—C14D—O2D | 123.6 (6) | C25—C24—H24C | 109.5 |
O3D—C14D—C11D | 116.6 (17) | H24A—C24—H24C | 109.5 |
O2D—C14D—C11D | 119.8 (17) | H24B—C24—H24C | 109.5 |
C16D—C15D—C2D | 111 (4) | C26—C25—N1 | 109.7 (5) |
C16D—C15D—C17D | 115 (4) | C26—C25—C24 | 114.9 (6) |
C2D—C15D—C17D | 111 (4) | N1—C25—C24 | 108.8 (5) |
C16D—C15D—H15D | 106.4 | C26—C25—H25 | 107.7 |
C2D—C15D—H15D | 106.4 | N1—C25—H25 | 107.7 |
C17D—C15D—H15D | 106.4 | C24—C25—H25 | 107.7 |
C15D—C16D—H16D | 109.5 | C27—C26—C31 | 118.1 (7) |
C15D—C16D—H16E | 109.5 | C27—C26—C25 | 120.3 (8) |
H16D—C16D—H16E | 109.5 | C31—C26—C25 | 121.6 (7) |
C15D—C16D—H16F | 109.5 | C26—C27—C28 | 121.8 (10) |
H16D—C16D—H16F | 109.5 | C26—C27—H27 | 119.1 |
H16E—C16D—H16F | 109.5 | C28—C27—H27 | 119.1 |
C15D—C17D—H17D | 109.5 | C29—C28—C27 | 118.5 (12) |
C15D—C17D—H17E | 109.5 | C29—C28—H28 | 120.8 |
H17D—C17D—H17E | 109.5 | C27—C28—H28 | 120.8 |
C15D—C17D—H17F | 109.5 | C30—C29—C28 | 121.6 (13) |
H17D—C17D—H17F | 109.5 | C30—C29—H29 | 119.2 |
H17E—C17D—H17F | 109.5 | C28—C29—H29 | 119.2 |
C19D—C18D—C20D | 113 (3) | C29—C30—C31 | 120.0 (12) |
C19D—C18D—C4D | 115 (3) | C29—C30—H30 | 120.0 |
C20D—C18D—C4D | 106 (3) | C31—C30—H30 | 120.0 |
C19D—C18D—H18D | 107.6 | C26—C31—C30 | 120.1 (10) |
C20D—C18D—H18D | 107.6 | C26—C31—H31 | 120.0 |
C4D—C18D—H18D | 107.6 | C30—C31—H31 | 120.0 |
C31H39NO3 | Dx = 1.121 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 2260 reflections |
a = 6.3387 (5) Å | θ = 1.6–18.1° |
b = 13.5668 (10) Å | µ = 0.07 mm−1 |
c = 32.6429 (16) Å | T = 299 K |
V = 2807.2 (3) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.12 × 0.10 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 5429 independent reflections |
Radiation source: fine-focus sealed tube | 1938 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.130 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −14→16 |
Tmin = 0.836, Tmax = 1.000 | l = −40→39 |
24938 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.086 | H-atom parameters constrained |
wR(F2) = 0.189 | w = 1/[σ2(Fo2) + (0.0262P)2 + 1.0565P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
5429 reflections | Δρmax = 0.13 e Å−3 |
484 parameters | Δρmin = −0.17 e Å−3 |
565 restraints | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −1.1 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.0508 (10) | 0.6678 (4) | 0.49214 (16) | 0.0657 (19) | |
H1A | 0.0626 | 0.7330 | 0.4901 | 0.079* | |
H1B | 0.1507 | 0.6449 | 0.5087 | 0.079* | |
H1C | −0.0755 | 0.6526 | 0.5023 | 0.079* | |
C24 | 0.2878 (14) | 0.6540 (6) | 0.4332 (3) | 0.093 (3)* | |
H24A | 0.2875 | 0.7240 | 0.4288 | 0.139* | |
H24B | 0.3122 | 0.6210 | 0.4076 | 0.139* | |
H24C | 0.3975 | 0.6371 | 0.4522 | 0.139* | |
C25 | 0.0753 (14) | 0.6222 (6) | 0.4505 (2) | 0.074 (2)* | |
H25 | −0.0354 | 0.6490 | 0.4327 | 0.089* | |
C26 | 0.0449 (19) | 0.5142 (8) | 0.4531 (3) | 0.079 (3) | |
C27 | −0.139 (2) | 0.4716 (9) | 0.4400 (3) | 0.104 (3) | |
H27 | −0.2459 | 0.5117 | 0.4300 | 0.125* | |
C28 | −0.170 (3) | 0.3683 (12) | 0.4411 (4) | 0.145 (6) | |
H28 | −0.2973 | 0.3403 | 0.4329 | 0.173* | |
C29 | −0.006 (4) | 0.3110 (14) | 0.4547 (6) | 0.170 (9) | |
H29 | −0.0201 | 0.2428 | 0.4543 | 0.204* | |
C30 | 0.176 (4) | 0.3512 (12) | 0.4688 (5) | 0.169 (7) | |
H30 | 0.2827 | 0.3110 | 0.4791 | 0.203* | |
C31 | 0.203 (2) | 0.4532 (9) | 0.4678 (3) | 0.110 (4) | |
H31 | 0.3287 | 0.4806 | 0.4771 | 0.132* | |
O1 | 1.050 (3) | 0.2471 (13) | 0.6341 (6) | 0.097 (6) | 0.560 (4) |
O2 | 0.6403 (10) | 0.6315 (4) | 0.51753 (16) | 0.0784 (17) | 0.560 (4) |
O3 | 0.3375 (11) | 0.6177 (5) | 0.55054 (17) | 0.091 (2) | 0.560 (4) |
C1 | 0.817 (4) | 0.2792 (17) | 0.6903 (6) | 0.064 (6) | 0.560 (4) |
C2 | 0.865 (5) | 0.3438 (17) | 0.7221 (7) | 0.071 (6) | 0.560 (4) |
C3 | 0.809 (5) | 0.325 (2) | 0.7624 (7) | 0.075 (6) | 0.560 (4) |
H3 | 0.8485 | 0.3678 | 0.7832 | 0.090* | 0.560 (4) |
C4 | 0.691 (5) | 0.2413 (17) | 0.7711 (5) | 0.059 (5) | 0.560 (4) |
C5 | 0.620 (5) | 0.1836 (18) | 0.7396 (6) | 0.064 (6) | 0.560 (4) |
H5 | 0.5288 | 0.1317 | 0.7453 | 0.076* | 0.560 (4) |
C6 | 0.683 (5) | 0.2007 (18) | 0.6993 (6) | 0.066 (6) | 0.560 (4) |
C7 | 0.901 (4) | 0.2936 (16) | 0.6477 (6) | 0.082 (6) | 0.560 (4) |
C8 | 0.798 (3) | 0.3706 (16) | 0.6212 (6) | 0.053 (6) | 0.560 (4) |
C9 | 0.908 (3) | 0.4047 (12) | 0.5876 (5) | 0.057 (5) | 0.560 (4) |
H9 | 1.0415 | 0.3805 | 0.5810 | 0.068* | 0.560 (4) |
C10 | 0.811 (3) | 0.4769 (14) | 0.5641 (6) | 0.061 (6) | 0.560 (4) |
H10 | 0.8872 | 0.5028 | 0.5423 | 0.074* | 0.560 (4) |
C11 | 0.6143 (17) | 0.5124 (7) | 0.5705 (3) | 0.057 (3)* | 0.560 (4) |
C12 | 0.498 (3) | 0.4691 (14) | 0.6025 (5) | 0.063 (5) | 0.560 (4) |
H12 | 0.3584 | 0.4874 | 0.6069 | 0.076* | 0.560 (4) |
C13 | 0.592 (4) | 0.3989 (18) | 0.6275 (6) | 0.069 (6) | 0.560 (4) |
H13 | 0.5152 | 0.3707 | 0.6488 | 0.083* | 0.560 (4) |
C14 | 0.5230 (16) | 0.5931 (6) | 0.5445 (2) | 0.068 (2) | 0.560 (4) |
C15 | 1.007 (4) | 0.4320 (16) | 0.7137 (8) | 0.084 (6) | 0.560 (4) |
H15 | 1.0145 | 0.4369 | 0.6838 | 0.101* | 0.560 (4) |
C16 | 1.229 (4) | 0.415 (3) | 0.7272 (16) | 0.097 (9) | 0.560 (4) |
H16A | 1.2761 | 0.3523 | 0.7174 | 0.146* | 0.560 (4) |
H16B | 1.3174 | 0.4662 | 0.7163 | 0.146* | 0.560 (4) |
H16C | 1.2350 | 0.4164 | 0.7566 | 0.146* | 0.560 (4) |
C17 | 0.919 (5) | 0.5297 (17) | 0.7277 (8) | 0.109 (8) | 0.560 (4) |
H17A | 0.7761 | 0.5363 | 0.7181 | 0.164* | 0.560 (4) |
H17B | 0.9205 | 0.5325 | 0.7571 | 0.164* | 0.560 (4) |
H17C | 1.0029 | 0.5823 | 0.7168 | 0.164* | 0.560 (4) |
C18 | 0.615 (4) | 0.2174 (18) | 0.8155 (6) | 0.084 (6) | 0.560 (4) |
H18 | 0.6259 | 0.1460 | 0.8197 | 0.101* | 0.560 (4) |
C19 | 0.755 (4) | 0.269 (2) | 0.8475 (6) | 0.121 (9) | 0.560 (4) |
H19A | 0.8988 | 0.2491 | 0.8438 | 0.181* | 0.560 (4) |
H19B | 0.7436 | 0.3390 | 0.8443 | 0.181* | 0.560 (4) |
H19C | 0.7089 | 0.2507 | 0.8745 | 0.181* | 0.560 (4) |
C20 | 0.385 (4) | 0.248 (3) | 0.8208 (8) | 0.112 (9) | 0.560 (4) |
H20A | 0.3004 | 0.2148 | 0.8005 | 0.168* | 0.560 (4) |
H20B | 0.3377 | 0.2293 | 0.8476 | 0.168* | 0.560 (4) |
H20C | 0.3724 | 0.3176 | 0.8174 | 0.168* | 0.560 (4) |
C21 | 0.610 (4) | 0.1339 (16) | 0.6650 (7) | 0.091 (6) | 0.560 (4) |
H21 | 0.5907 | 0.1725 | 0.6399 | 0.110* | 0.560 (4) |
C22 | 0.778 (3) | 0.0547 (16) | 0.6580 (6) | 0.105 (7) | 0.560 (4) |
H22A | 0.7335 | 0.0117 | 0.6363 | 0.157* | 0.560 (4) |
H22B | 0.9089 | 0.0854 | 0.6506 | 0.157* | 0.560 (4) |
H22C | 0.7966 | 0.0171 | 0.6826 | 0.157* | 0.560 (4) |
C23 | 0.394 (3) | 0.0806 (16) | 0.6767 (6) | 0.114 (7) | 0.560 (4) |
H23A | 0.3505 | 0.0386 | 0.6546 | 0.171* | 0.560 (4) |
H23B | 0.4140 | 0.0417 | 0.7010 | 0.171* | 0.560 (4) |
H23C | 0.2871 | 0.1293 | 0.6817 | 0.171* | 0.560 (4) |
O1D | 1.092 (5) | 0.279 (3) | 0.6422 (15) | 0.086 (15)* | 0.299 (4) |
O2D | 0.6403 (10) | 0.6315 (4) | 0.51753 (16) | 0.0784 (17) | 0.299 (4) |
O3D | 0.3375 (11) | 0.6177 (5) | 0.55054 (17) | 0.091 (2) | 0.299 (4) |
C1D | 0.808 (8) | 0.287 (3) | 0.6916 (10) | 0.069 (10)* | 0.299 (4) |
C2D | 0.908 (7) | 0.348 (3) | 0.7192 (11) | 0.070 (10)* | 0.299 (4) |
C3D | 0.854 (7) | 0.339 (3) | 0.7605 (11) | 0.075 (10)* | 0.299 (4) |
H3D | 0.9240 | 0.3770 | 0.7798 | 0.090* | 0.299 (4) |
C4D | 0.693 (7) | 0.273 (3) | 0.7737 (9) | 0.065 (10)* | 0.299 (4) |
C5D | 0.608 (8) | 0.209 (3) | 0.7443 (10) | 0.070 (11)* | 0.299 (4) |
H5D | 0.5114 | 0.1619 | 0.7525 | 0.084* | 0.299 (4) |
C6D | 0.664 (9) | 0.215 (3) | 0.7031 (10) | 0.063 (10)* | 0.299 (4) |
C7D | 0.866 (5) | 0.277 (2) | 0.6455 (9) | 0.079 (10)* | 0.299 (4) |
C8D | 0.765 (7) | 0.357 (3) | 0.6187 (11) | 0.049 (10)* | 0.299 (4) |
C9D | 0.862 (6) | 0.379 (2) | 0.5817 (10) | 0.064 (10)* | 0.299 (4) |
H9D | 0.9770 | 0.3422 | 0.5728 | 0.077* | 0.299 (4) |
C10D | 0.785 (5) | 0.456 (3) | 0.5581 (11) | 0.058 (10)* | 0.299 (4) |
H10D | 0.8501 | 0.4701 | 0.5332 | 0.070* | 0.299 (4) |
C11D | 0.6143 (17) | 0.5124 (7) | 0.5705 (3) | 0.057 (3)* | 0.299 (4) |
C12D | 0.522 (6) | 0.491 (3) | 0.6086 (9) | 0.053 (10)* | 0.299 (4) |
H12D | 0.4081 | 0.5279 | 0.6179 | 0.064* | 0.299 (4) |
C13D | 0.602 (7) | 0.415 (3) | 0.6321 (13) | 0.064 (11)* | 0.299 (4) |
H13D | 0.5424 | 0.4024 | 0.6577 | 0.077* | 0.299 (4) |
C14D | 0.5230 (16) | 0.5931 (6) | 0.5445 (2) | 0.068 (2) | 0.299 (4) |
C15D | 1.057 (7) | 0.429 (3) | 0.7058 (15) | 0.081 (10)* | 0.299 (4) |
H15D | 1.0924 | 0.4200 | 0.6768 | 0.097* | 0.299 (4) |
C16D | 1.254 (9) | 0.429 (5) | 0.730 (3) | 0.091 (17)* | 0.299 (4) |
H16D | 1.3447 | 0.4815 | 0.7212 | 0.136* | 0.299 (4) |
H16E | 1.2205 | 0.4390 | 0.7588 | 0.136* | 0.299 (4) |
H16F | 1.3252 | 0.3672 | 0.7271 | 0.136* | 0.299 (4) |
C17D | 0.932 (11) | 0.527 (3) | 0.7108 (17) | 0.078 (15)* | 0.299 (4) |
H17D | 0.8063 | 0.5243 | 0.6945 | 0.118* | 0.299 (4) |
H17E | 0.8953 | 0.5359 | 0.7391 | 0.118* | 0.299 (4) |
H17F | 1.0183 | 0.5811 | 0.7019 | 0.118* | 0.299 (4) |
C18D | 0.643 (6) | 0.249 (4) | 0.8194 (10) | 0.093 (11)* | 0.299 (4) |
H18D | 0.6338 | 0.1783 | 0.8145 | 0.112* | 0.299 (4) |
C19D | 0.811 (8) | 0.238 (4) | 0.8509 (15) | 0.108 (18)* | 0.299 (4) |
H19D | 0.9462 | 0.2341 | 0.8377 | 0.163* | 0.299 (4) |
H19E | 0.8089 | 0.2939 | 0.8690 | 0.163* | 0.299 (4) |
H19F | 0.7865 | 0.1790 | 0.8664 | 0.163* | 0.299 (4) |
C20D | 0.413 (6) | 0.258 (6) | 0.8318 (15) | 0.089 (15)* | 0.299 (4) |
H20D | 0.3273 | 0.2645 | 0.8077 | 0.133* | 0.299 (4) |
H20E | 0.3718 | 0.1993 | 0.8464 | 0.133* | 0.299 (4) |
H20F | 0.3943 | 0.3142 | 0.8490 | 0.133* | 0.299 (4) |
C21D | 0.602 (7) | 0.155 (3) | 0.6648 (12) | 0.108 (11)* | 0.299 (4) |
H21D | 0.4797 | 0.1891 | 0.6530 | 0.129* | 0.299 (4) |
C22D | 0.784 (5) | 0.1739 (19) | 0.6352 (9) | 0.104 (11)* | 0.299 (4) |
H22D | 0.8943 | 0.1251 | 0.6390 | 0.125* | 0.299 (4) |
H22E | 0.7357 | 0.1711 | 0.6071 | 0.125* | 0.299 (4) |
C23D | 0.535 (7) | 0.049 (3) | 0.6703 (13) | 0.125 (12)* | 0.299 (4) |
H23D | 0.4202 | 0.0460 | 0.6894 | 0.188* | 0.299 (4) |
H23E | 0.4911 | 0.0227 | 0.6444 | 0.188* | 0.299 (4) |
H23F | 0.6519 | 0.0115 | 0.6806 | 0.188* | 0.299 (4) |
O1P | 1.125 (7) | 0.302 (3) | 0.6514 (14) | 0.068 (15)* | 0.141 (4) |
O2P | 0.6403 (10) | 0.6315 (4) | 0.51753 (16) | 0.0784 (17) | 0.141 (4) |
O3P | 0.3375 (11) | 0.6177 (5) | 0.55054 (17) | 0.091 (2) | 0.141 (4) |
C1P | 0.838 (9) | 0.294 (4) | 0.7007 (13) | 0.061 (13)* | 0.141 (4) |
C2P | 0.877 (12) | 0.356 (4) | 0.7332 (13) | 0.066 (13)* | 0.141 (4) |
C3P | 0.797 (16) | 0.333 (6) | 0.7719 (15) | 0.075 (12)* | 0.141 (4) |
H3P | 0.8260 | 0.3719 | 0.7946 | 0.090* | 0.141 (4) |
C4P | 0.674 (15) | 0.248 (6) | 0.7752 (16) | 0.063 (13)* | 0.141 (4) |
C5P | 0.650 (17) | 0.182 (6) | 0.7431 (17) | 0.061 (13)* | 0.141 (4) |
H5P | 0.5869 | 0.1210 | 0.7474 | 0.074* | 0.141 (4) |
C6P | 0.724 (9) | 0.208 (4) | 0.7047 (15) | 0.068 (13)* | 0.141 (4) |
C7P | 0.954 (6) | 0.352 (3) | 0.6688 (10) | 0.082 (12)* | 0.141 (4) |
C8P | 0.843 (6) | 0.414 (2) | 0.6367 (9) | 0.051 (12)* | 0.141 (4) |
C9P | 0.955 (6) | 0.453 (3) | 0.6043 (12) | 0.061 (9)* | 0.141 (4) |
H9P | 1.0975 | 0.4383 | 0.6018 | 0.073* | 0.141 (4) |
C10P | 0.861 (6) | 0.515 (3) | 0.5751 (13) | 0.056 (9)* | 0.141 (4) |
H10P | 0.9432 | 0.5414 | 0.5542 | 0.067* | 0.141 (4) |
C11P | 0.647 (6) | 0.536 (3) | 0.5769 (11) | 0.050 (15)* | 0.141 (4) |
C12P | 0.531 (7) | 0.493 (5) | 0.6088 (17) | 0.056 (9)* | 0.141 (4) |
H12P | 0.3863 | 0.5046 | 0.6106 | 0.067* | 0.141 (4) |
C13P | 0.627 (7) | 0.433 (4) | 0.6378 (15) | 0.061 (9)* | 0.141 (4) |
H13P | 0.5453 | 0.4049 | 0.6584 | 0.073* | 0.141 (4) |
C14P | 0.5230 (16) | 0.5931 (6) | 0.5445 (2) | 0.068 (2) | 0.141 (4) |
C15P | 1.008 (9) | 0.426 (3) | 0.7081 (13) | 0.084 (13)* | 0.141 (4) |
C16P | 1.244 (10) | 0.436 (7) | 0.712 (2) | 0.12 (2)* | 0.141 (4) |
H16G | 1.2950 | 0.4842 | 0.6933 | 0.176* | 0.141 (4) |
H16H | 1.2784 | 0.4560 | 0.7398 | 0.176* | 0.141 (4) |
H16I | 1.3101 | 0.3735 | 0.7067 | 0.176* | 0.141 (4) |
C17P | 0.909 (17) | 0.527 (4) | 0.703 (3) | 0.11 (2)* | 0.141 (4) |
H17G | 0.9993 | 0.5684 | 0.6869 | 0.158* | 0.141 (4) |
H17H | 0.7742 | 0.5210 | 0.6899 | 0.158* | 0.141 (4) |
H17I | 0.8894 | 0.5568 | 0.7297 | 0.158* | 0.141 (4) |
C18P | 0.585 (11) | 0.222 (5) | 0.8171 (16) | 0.086 (13)* | 0.141 (4) |
H18P | 0.4969 | 0.1627 | 0.8157 | 0.103* | 0.141 (4) |
C19P | 0.767 (14) | 0.209 (7) | 0.847 (3) | 0.11 (2)* | 0.141 (4) |
H19G | 0.7126 | 0.1918 | 0.8736 | 0.172* | 0.141 (4) |
H19H | 0.8582 | 0.1568 | 0.8376 | 0.172* | 0.141 (4) |
H19I | 0.8461 | 0.2689 | 0.8489 | 0.172* | 0.141 (4) |
C20P | 0.455 (11) | 0.313 (5) | 0.828 (2) | 0.085 (19)* | 0.141 (4) |
H20G | 0.3908 | 0.3043 | 0.8543 | 0.128* | 0.141 (4) |
H20H | 0.5452 | 0.3700 | 0.8286 | 0.128* | 0.141 (4) |
H20I | 0.3470 | 0.3227 | 0.8077 | 0.128* | 0.141 (4) |
C21P | 0.700 (10) | 0.148 (4) | 0.6659 (17) | 0.092 (13)* | 0.141 (4) |
H21P | 0.7073 | 0.1945 | 0.6429 | 0.111* | 0.141 (4) |
C22P | 0.887 (10) | 0.079 (6) | 0.662 (3) | 0.11 (2)* | 0.141 (4) |
H22F | 0.8731 | 0.0405 | 0.6374 | 0.166* | 0.141 (4) |
H22G | 1.0153 | 0.1161 | 0.6610 | 0.166* | 0.141 (4) |
H22H | 0.8905 | 0.0353 | 0.6853 | 0.166* | 0.141 (4) |
C23P | 0.488 (10) | 0.096 (7) | 0.663 (3) | 0.123 (15)* | 0.141 (4) |
H23G | 0.4801 | 0.0592 | 0.6384 | 0.184* | 0.141 (4) |
H23H | 0.4736 | 0.0520 | 0.6863 | 0.184* | 0.141 (4) |
H23I | 0.3766 | 0.1440 | 0.6641 | 0.184* | 0.141 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.071 (5) | 0.082 (4) | 0.044 (4) | 0.007 (4) | −0.001 (4) | 0.008 (3) |
C26 | 0.089 (8) | 0.103 (8) | 0.045 (5) | −0.003 (8) | 0.001 (5) | −0.009 (5) |
C27 | 0.105 (11) | 0.123 (10) | 0.085 (8) | −0.009 (8) | 0.008 (7) | −0.023 (7) |
C28 | 0.171 (17) | 0.139 (14) | 0.124 (11) | −0.051 (13) | 0.036 (11) | −0.041 (10) |
C29 | 0.26 (3) | 0.112 (14) | 0.141 (15) | −0.019 (15) | 0.032 (17) | −0.013 (11) |
C30 | 0.26 (2) | 0.108 (14) | 0.137 (13) | 0.028 (13) | −0.004 (14) | −0.008 (10) |
C31 | 0.140 (12) | 0.092 (9) | 0.099 (8) | −0.001 (8) | −0.010 (8) | −0.007 (7) |
O1 | 0.117 (13) | 0.083 (13) | 0.091 (11) | 0.039 (11) | 0.046 (10) | 0.017 (10) |
O2 | 0.081 (4) | 0.087 (4) | 0.068 (3) | −0.004 (4) | 0.010 (3) | 0.029 (3) |
O3 | 0.072 (4) | 0.135 (5) | 0.066 (4) | 0.031 (4) | 0.000 (4) | 0.029 (4) |
C1 | 0.067 (11) | 0.062 (10) | 0.062 (10) | 0.016 (9) | −0.004 (9) | 0.016 (9) |
C2 | 0.069 (13) | 0.059 (10) | 0.085 (12) | 0.000 (9) | 0.006 (11) | 0.016 (10) |
C3 | 0.073 (13) | 0.066 (11) | 0.087 (12) | −0.011 (10) | −0.017 (11) | −0.010 (10) |
C4 | 0.069 (11) | 0.053 (11) | 0.054 (9) | 0.005 (10) | 0.003 (8) | 0.008 (9) |
C5 | 0.087 (13) | 0.050 (11) | 0.054 (9) | 0.000 (11) | −0.006 (9) | 0.005 (8) |
C6 | 0.081 (13) | 0.055 (10) | 0.061 (10) | 0.016 (10) | −0.006 (9) | 0.010 (8) |
C7 | 0.099 (14) | 0.081 (12) | 0.067 (11) | 0.000 (11) | 0.006 (10) | 0.017 (10) |
C8 | 0.048 (10) | 0.051 (10) | 0.062 (10) | −0.008 (9) | −0.006 (9) | 0.004 (8) |
C9 | 0.055 (10) | 0.045 (9) | 0.071 (10) | −0.011 (9) | 0.009 (9) | 0.007 (9) |
C10 | 0.081 (12) | 0.053 (11) | 0.050 (9) | −0.011 (10) | −0.003 (9) | 0.008 (9) |
C12 | 0.054 (10) | 0.070 (11) | 0.065 (10) | −0.005 (10) | 0.005 (9) | 0.000 (10) |
C13 | 0.083 (12) | 0.083 (12) | 0.040 (9) | −0.004 (11) | 0.006 (9) | 0.012 (9) |
C14 | 0.100 (7) | 0.061 (5) | 0.042 (5) | 0.011 (5) | −0.009 (5) | 0.006 (4) |
C15 | 0.061 (12) | 0.101 (12) | 0.090 (13) | 0.008 (11) | −0.004 (11) | 0.024 (10) |
C16 | 0.105 (18) | 0.098 (17) | 0.088 (18) | −0.034 (13) | 0.015 (15) | −0.015 (15) |
C17 | 0.104 (16) | 0.093 (14) | 0.13 (2) | −0.021 (12) | 0.009 (18) | 0.007 (15) |
C18 | 0.092 (13) | 0.086 (12) | 0.075 (10) | −0.002 (11) | −0.009 (10) | −0.023 (9) |
C19 | 0.14 (2) | 0.16 (2) | 0.064 (12) | 0.030 (18) | −0.034 (14) | 0.003 (14) |
C20 | 0.133 (19) | 0.13 (2) | 0.069 (14) | −0.003 (17) | 0.028 (14) | −0.036 (14) |
C21 | 0.113 (14) | 0.081 (12) | 0.080 (10) | −0.035 (12) | −0.016 (11) | −0.013 (10) |
C22 | 0.123 (18) | 0.122 (16) | 0.070 (11) | 0.011 (15) | −0.016 (13) | −0.029 (11) |
C23 | 0.113 (15) | 0.127 (13) | 0.101 (12) | −0.029 (13) | −0.007 (12) | 0.012 (11) |
O2D | 0.081 (4) | 0.087 (4) | 0.068 (3) | −0.004 (4) | 0.010 (3) | 0.029 (3) |
O3D | 0.072 (4) | 0.135 (5) | 0.066 (4) | 0.031 (4) | 0.000 (4) | 0.029 (4) |
C14D | 0.100 (7) | 0.061 (5) | 0.042 (5) | 0.011 (5) | −0.009 (5) | 0.006 (4) |
O2P | 0.081 (4) | 0.087 (4) | 0.068 (3) | −0.004 (4) | 0.010 (3) | 0.029 (3) |
O3P | 0.072 (4) | 0.135 (5) | 0.066 (4) | 0.031 (4) | 0.000 (4) | 0.029 (4) |
C14P | 0.100 (7) | 0.061 (5) | 0.042 (5) | 0.011 (5) | −0.009 (5) | 0.006 (4) |
N1—C25 | 1.502 (9) | C8D—C13D | 1.37 (2) |
N1—H1A | 0.8900 | C8D—C9D | 1.39 (2) |
N1—H1B | 0.8900 | C9D—C10D | 1.39 (2) |
N1—H1C | 0.8900 | C9D—H9D | 0.9300 |
C24—C25 | 1.523 (11) | C10D—C11D | 1.39 (2) |
C24—H24A | 0.9600 | C10D—H10D | 0.9300 |
C24—H24B | 0.9600 | C11D—C12D | 1.40 (2) |
C24—H24C | 0.9600 | C11D—C14D | 1.501 (10) |
C25—C26 | 1.480 (12) | C12D—C13D | 1.38 (2) |
C25—H25 | 0.9800 | C12D—H12D | 0.9300 |
C26—C27 | 1.368 (14) | C13D—H13D | 0.9300 |
C26—C31 | 1.386 (14) | C15D—C16D | 1.49 (3) |
C27—C28 | 1.416 (15) | C15D—C17D | 1.55 (3) |
C27—H27 | 0.9300 | C15D—H15D | 0.9800 |
C28—C29 | 1.37 (2) | C16D—H16D | 0.9600 |
C28—H28 | 0.9300 | C16D—H16E | 0.9600 |
C29—C30 | 1.36 (2) | C16D—H16F | 0.9600 |
C29—H29 | 0.9300 | C17D—H17D | 0.9600 |
C30—C31 | 1.394 (16) | C17D—H17E | 0.9600 |
C30—H30 | 0.9300 | C17D—H17F | 0.9600 |
C31—H31 | 0.9300 | C18D—C19D | 1.49 (2) |
O1—C7 | 1.221 (17) | C18D—C20D | 1.52 (2) |
O2—C14 | 1.265 (8) | C18D—H18D | 0.9800 |
O3—C14 | 1.238 (9) | C19D—H19D | 0.9600 |
C1—C6 | 1.391 (17) | C19D—H19E | 0.9600 |
C1—C2 | 1.393 (17) | C19D—H19F | 0.9600 |
C1—C7 | 1.503 (17) | C20D—H20D | 0.9600 |
C2—C3 | 1.388 (17) | C20D—H20E | 0.9600 |
C2—C15 | 1.521 (18) | C20D—H20F | 0.9600 |
C3—C4 | 1.387 (18) | C21D—C23D | 1.51 (3) |
C3—H3 | 0.9300 | C21D—C22D | 1.53 (2) |
C4—C5 | 1.368 (18) | C21D—H21D | 0.9800 |
C4—C18 | 1.560 (17) | C22D—H22D | 0.9700 |
C5—C6 | 1.396 (16) | C22D—H22E | 0.9700 |
C5—H5 | 0.9300 | C23D—H23D | 0.9600 |
C6—C21 | 1.513 (17) | C23D—H23E | 0.9600 |
C7—C8 | 1.504 (16) | C23D—H23F | 0.9600 |
C8—C13 | 1.378 (18) | O1P—C7P | 1.40 (2) |
C8—C9 | 1.380 (16) | O2P—C14P | 1.265 (8) |
C9—C10 | 1.388 (15) | O3P—C14P | 1.238 (9) |
C9—H9 | 0.9300 | C1P—C2P | 1.38 (2) |
C10—C11 | 1.354 (16) | C1P—C6P | 1.38 (2) |
C10—H10 | 0.9300 | C1P—C7P | 1.50 (2) |
C11—C12 | 1.408 (15) | C2P—C3P | 1.39 (2) |
C11—C14 | 1.501 (10) | C2P—C15P | 1.50 (2) |
C12—C13 | 1.390 (16) | C3P—C4P | 1.39 (3) |
C12—H12 | 0.9300 | C3P—H3P | 0.9300 |
C13—H13 | 0.9300 | C4P—C5P | 1.39 (2) |
C15—C16 | 1.488 (19) | C4P—C18P | 1.52 (2) |
C15—C17 | 1.510 (19) | C5P—C6P | 1.38 (2) |
C15—H15 | 0.9800 | C5P—H5P | 0.9300 |
C16—H16A | 0.9600 | C6P—C21P | 1.51 (2) |
C16—H16B | 0.9600 | C7P—C8P | 1.52 (2) |
C16—H16C | 0.9600 | C7P—C15P | 1.67 (2) |
C17—H17A | 0.9600 | C8P—C9P | 1.38 (2) |
C17—H17B | 0.9600 | C8P—C13P | 1.39 (2) |
C17—H17C | 0.9600 | C9P—C10P | 1.40 (2) |
C18—C20 | 1.53 (2) | C9P—H9P | 0.9300 |
C18—C19 | 1.54 (2) | C10P—C11P | 1.39 (2) |
C18—H18 | 0.9800 | C10P—H10P | 0.9300 |
C19—H19A | 0.9600 | C11P—C12P | 1.40 (2) |
C19—H19B | 0.9600 | C11P—C14P | 1.53 (2) |
C19—H19C | 0.9600 | C12P—C13P | 1.39 (2) |
C20—H20A | 0.9600 | C12P—H12P | 0.9300 |
C20—H20B | 0.9600 | C13P—H13P | 0.9300 |
C20—H20C | 0.9600 | C15P—C16P | 1.51 (3) |
C21—C22 | 1.53 (2) | C15P—C17P | 1.53 (3) |
C21—C23 | 1.596 (19) | C16P—H16G | 0.9600 |
C21—H21 | 0.9800 | C16P—H16H | 0.9600 |
C22—H22A | 0.9600 | C16P—H16I | 0.9600 |
C22—H22B | 0.9600 | C17P—H17G | 0.9600 |
C22—H22C | 0.9600 | C17P—H17H | 0.9600 |
C23—H23A | 0.9600 | C17P—H17I | 0.9600 |
C23—H23B | 0.9600 | C18P—C19P | 1.52 (3) |
C23—H23C | 0.9600 | C18P—C20P | 1.53 (3) |
O1D—C7D | 1.44 (2) | C18P—H18P | 0.9800 |
O2D—C14D | 1.265 (8) | C19P—H19G | 0.9600 |
O3D—C14D | 1.238 (9) | C19P—H19H | 0.9600 |
C1D—C2D | 1.37 (2) | C19P—H19I | 0.9600 |
C1D—C6D | 1.40 (2) | C20P—H20G | 0.9600 |
C1D—C7D | 1.56 (2) | C20P—H20H | 0.9600 |
C2D—C3D | 1.40 (2) | C20P—H20I | 0.9600 |
C2D—C15D | 1.52 (2) | C21P—C22P | 1.52 (3) |
C3D—C4D | 1.42 (2) | C21P—C23P | 1.52 (3) |
C3D—H3D | 0.9300 | C21P—H21P | 0.9800 |
C4D—C5D | 1.40 (2) | C22P—H22F | 0.9600 |
C4D—C18D | 1.56 (2) | C22P—H22G | 0.9600 |
C5D—C6D | 1.39 (2) | C22P—H22H | 0.9600 |
C5D—H5D | 0.9300 | C23P—H23G | 0.9600 |
C6D—C21D | 1.54 (2) | C23P—H23H | 0.9600 |
C7D—C22D | 1.53 (2) | C23P—H23I | 0.9600 |
C7D—C8D | 1.54 (2) | ||
C25—N1—H1A | 109.5 | C10D—C11D—C12D | 118 (2) |
C25—N1—H1B | 109.5 | C10D—C11D—C14D | 122.7 (15) |
H1A—N1—H1B | 109.5 | C12D—C11D—C14D | 119.3 (16) |
C25—N1—H1C | 109.5 | C13D—C12D—C11D | 120 (3) |
H1A—N1—H1C | 109.5 | C13D—C12D—H12D | 120.2 |
H1B—N1—H1C | 109.5 | C11D—C12D—H12D | 120.2 |
C25—C24—H24A | 109.5 | C8D—C13D—C12D | 122 (3) |
C25—C24—H24B | 109.5 | C8D—C13D—H13D | 119.1 |
H24A—C24—H24B | 109.5 | C12D—C13D—H13D | 119.1 |
C25—C24—H24C | 109.5 | O3D—C14D—O2D | 123.9 (8) |
H24A—C24—H24C | 109.5 | O3D—C14D—C11D | 118.3 (8) |
H24B—C24—H24C | 109.5 | O2D—C14D—C11D | 117.8 (8) |
C26—C25—N1 | 109.9 (7) | C16D—C15D—C2D | 112 (3) |
C26—C25—C24 | 114.6 (8) | C16D—C15D—C17D | 112 (3) |
N1—C25—C24 | 108.1 (7) | C2D—C15D—C17D | 106 (3) |
C26—C25—H25 | 108.0 | C16D—C15D—H15D | 109.1 |
N1—C25—H25 | 108.0 | C2D—C15D—H15D | 109.1 |
C24—C25—H25 | 108.0 | C17D—C15D—H15D | 109.1 |
C27—C26—C31 | 118.1 (10) | C15D—C16D—H16D | 109.5 |
C27—C26—C25 | 120.7 (11) | C15D—C16D—H16E | 109.5 |
C31—C26—C25 | 121.2 (10) | H16D—C16D—H16E | 109.5 |
C26—C27—C28 | 122.0 (13) | C15D—C16D—H16F | 109.5 |
C26—C27—H27 | 119.0 | H16D—C16D—H16F | 109.5 |
C28—C27—H27 | 119.0 | H16E—C16D—H16F | 109.5 |
C29—C28—C27 | 117.5 (18) | C15D—C17D—H17D | 109.5 |
C29—C28—H28 | 121.3 | C15D—C17D—H17E | 109.5 |
C27—C28—H28 | 121.3 | H17D—C17D—H17E | 109.5 |
C30—C29—C28 | 122 (2) | C15D—C17D—H17F | 109.5 |
C30—C29—H29 | 119.1 | H17D—C17D—H17F | 109.5 |
C28—C29—H29 | 119.1 | H17E—C17D—H17F | 109.5 |
C29—C30—C31 | 119.6 (19) | C19D—C18D—C20D | 121 (3) |
C29—C30—H30 | 120.2 | C19D—C18D—C4D | 123 (3) |
C31—C30—H30 | 120.2 | C20D—C18D—C4D | 116 (3) |
C26—C31—C30 | 120.9 (14) | C19D—C18D—H18D | 93.2 |
C26—C31—H31 | 119.6 | C20D—C18D—H18D | 93.2 |
C30—C31—H31 | 119.6 | C4D—C18D—H18D | 93.2 |
C6—C1—C2 | 117.4 (14) | C18D—C19D—H19D | 109.5 |
C6—C1—C7 | 120.7 (16) | C18D—C19D—H19E | 109.5 |
C2—C1—C7 | 121.9 (17) | H19D—C19D—H19E | 109.5 |
C3—C2—C1 | 122.1 (15) | C18D—C19D—H19F | 109.5 |
C3—C2—C15 | 118.0 (17) | H19D—C19D—H19F | 109.5 |
C1—C2—C15 | 119.5 (17) | H19E—C19D—H19F | 109.5 |
C4—C3—C2 | 119.1 (16) | C18D—C20D—H20D | 109.5 |
C4—C3—H3 | 120.5 | C18D—C20D—H20E | 109.5 |
C2—C3—H3 | 120.5 | H20D—C20D—H20E | 109.5 |
C5—C4—C3 | 119.3 (15) | C18D—C20D—H20F | 109.5 |
C5—C4—C18 | 118.5 (15) | H20D—C20D—H20F | 109.5 |
C3—C4—C18 | 121.8 (16) | H20E—C20D—H20F | 109.5 |
C4—C5—C6 | 121.4 (16) | C23D—C21D—C22D | 116 (3) |
C4—C5—H5 | 119.3 | C23D—C21D—C6D | 118 (3) |
C6—C5—H5 | 119.3 | C22D—C21D—C6D | 103 (2) |
C1—C6—C5 | 119.9 (15) | C23D—C21D—H21D | 105.8 |
C1—C6—C21 | 119.3 (15) | C22D—C21D—H21D | 105.8 |
C5—C6—C21 | 120.8 (16) | C6D—C21D—H21D | 105.8 |
O1—C7—C1 | 123.0 (17) | C7D—C22D—C21D | 106 (2) |
O1—C7—C8 | 119.0 (16) | C7D—C22D—H22D | 110.6 |
C1—C7—C8 | 118.0 (17) | C21D—C22D—H22D | 110.6 |
C13—C8—C9 | 120.5 (15) | C7D—C22D—H22E | 110.6 |
C13—C8—C7 | 121.1 (16) | C21D—C22D—H22E | 110.6 |
C9—C8—C7 | 118.1 (15) | H22D—C22D—H22E | 108.7 |
C8—C9—C10 | 116.8 (15) | C21D—C23D—H23D | 109.5 |
C8—C9—H9 | 121.6 | C21D—C23D—H23E | 109.5 |
C10—C9—H9 | 121.6 | H23D—C23D—H23E | 109.5 |
C11—C10—C9 | 125.2 (15) | C21D—C23D—H23F | 109.5 |
C11—C10—H10 | 117.4 | H23D—C23D—H23F | 109.5 |
C9—C10—H10 | 117.4 | H23E—C23D—H23F | 109.5 |
C10—C11—C12 | 116.6 (12) | C2P—C1P—C6P | 123 (3) |
C10—C11—C14 | 121.9 (11) | C2P—C1P—C7P | 97 (2) |
C12—C11—C14 | 121.4 (11) | C6P—C1P—C7P | 140 (3) |
C13—C12—C11 | 119.8 (16) | C1P—C2P—C3P | 119 (3) |
C13—C12—H12 | 120.1 | C1P—C2P—C15P | 94 (2) |
C11—C12—H12 | 120.1 | C3P—C2P—C15P | 147 (3) |
C8—C13—C12 | 120.6 (17) | C4P—C3P—C2P | 118 (3) |
C8—C13—H13 | 119.7 | C4P—C3P—H3P | 121.2 |
C12—C13—H13 | 119.7 | C2P—C3P—H3P | 121.2 |
O3—C14—O2 | 123.9 (8) | C3P—C4P—C5P | 122 (3) |
O3—C14—C11 | 118.3 (8) | C3P—C4P—C18P | 118 (3) |
O2—C14—C11 | 117.8 (8) | C5P—C4P—C18P | 119 (3) |
C16—C15—C17 | 113 (2) | C6P—C5P—C4P | 119 (3) |
C16—C15—C2 | 112.5 (19) | C6P—C5P—H5P | 120.6 |
C17—C15—C2 | 114.6 (18) | C4P—C5P—H5P | 120.6 |
C16—C15—H15 | 105.1 | C1P—C6P—C5P | 118 (3) |
C17—C15—H15 | 105.1 | C1P—C6P—C21P | 115 (3) |
C2—C15—H15 | 105.1 | C5P—C6P—C21P | 126 (3) |
C15—C16—H16A | 109.5 | O1P—C7P—C1P | 114 (3) |
C15—C16—H16B | 109.5 | O1P—C7P—C8P | 110 (2) |
H16A—C16—H16B | 109.5 | C1P—C7P—C8P | 123 (3) |
C15—C16—H16C | 109.5 | O1P—C7P—C15P | 116 (3) |
H16A—C16—H16C | 109.5 | C1P—C7P—C15P | 83.1 (19) |
H16B—C16—H16C | 109.5 | C8P—C7P—C15P | 107 (2) |
C15—C17—H17A | 109.5 | C9P—C8P—C13P | 117 (2) |
C15—C17—H17B | 109.5 | C9P—C8P—C7P | 120 (3) |
H17A—C17—H17B | 109.5 | C13P—C8P—C7P | 123 (3) |
C15—C17—H17C | 109.5 | C8P—C9P—C10P | 122 (3) |
H17A—C17—H17C | 109.5 | C8P—C9P—H9P | 118.9 |
H17B—C17—H17C | 109.5 | C10P—C9P—H9P | 118.9 |
C20—C18—C19 | 110.6 (19) | C11P—C10P—C9P | 121 (3) |
C20—C18—C4 | 110.1 (18) | C11P—C10P—H10P | 119.7 |
C19—C18—C4 | 111.1 (16) | C9P—C10P—H10P | 119.7 |
C20—C18—H18 | 108.3 | C10P—C11P—C12P | 117 (2) |
C19—C18—H18 | 108.3 | C10P—C11P—C14P | 125 (3) |
C4—C18—H18 | 108.3 | C12P—C11P—C14P | 117 (3) |
C18—C19—H19A | 109.5 | C13P—C12P—C11P | 121 (3) |
C18—C19—H19B | 109.5 | C13P—C12P—H12P | 119.4 |
H19A—C19—H19B | 109.5 | C11P—C12P—H12P | 119.4 |
C18—C19—H19C | 109.5 | C12P—C13P—C8P | 122 (3) |
H19A—C19—H19C | 109.5 | C12P—C13P—H13P | 119.2 |
H19B—C19—H19C | 109.5 | C8P—C13P—H13P | 119.2 |
C18—C20—H20A | 109.5 | O3P—C14P—O2P | 123.9 (8) |
C18—C20—H20B | 109.5 | O3P—C14P—C11P | 121.0 (16) |
H20A—C20—H20B | 109.5 | O2P—C14P—C11P | 112.9 (16) |
C18—C20—H20C | 109.5 | C2P—C15P—C16P | 124 (4) |
H20A—C20—H20C | 109.5 | C2P—C15P—C17P | 113 (3) |
H20B—C20—H20C | 109.5 | C16P—C15P—C17P | 110 (3) |
C6—C21—C22 | 108.6 (19) | C2P—C15P—C7P | 85.9 (19) |
C6—C21—C23 | 110.9 (16) | C16P—C15P—C7P | 109 (3) |
C22—C21—C23 | 108.3 (16) | C17P—C15P—C7P | 112 (3) |
C6—C21—H21 | 109.7 | C15P—C16P—H16G | 109.5 |
C22—C21—H21 | 109.7 | C15P—C16P—H16H | 109.5 |
C23—C21—H21 | 109.7 | H16G—C16P—H16H | 109.5 |
C21—C22—H22A | 109.5 | C15P—C16P—H16I | 109.5 |
C21—C22—H22B | 109.5 | H16G—C16P—H16I | 109.5 |
H22A—C22—H22B | 109.5 | H16H—C16P—H16I | 109.5 |
C21—C22—H22C | 109.5 | C15P—C17P—H17G | 109.5 |
H22A—C22—H22C | 109.5 | C15P—C17P—H17H | 109.5 |
H22B—C22—H22C | 109.5 | H17G—C17P—H17H | 109.5 |
C21—C23—H23A | 109.5 | C15P—C17P—H17I | 109.5 |
C21—C23—H23B | 109.5 | H17G—C17P—H17I | 109.5 |
H23A—C23—H23B | 109.5 | H17H—C17P—H17I | 109.5 |
C21—C23—H23C | 109.5 | C4P—C18P—C19P | 109 (4) |
H23A—C23—H23C | 109.5 | C4P—C18P—C20P | 102 (3) |
H23B—C23—H23C | 109.5 | C19P—C18P—C20P | 111 (4) |
C2D—C1D—C6D | 123 (2) | C4P—C18P—H18P | 111.4 |
C2D—C1D—C7D | 126 (2) | C19P—C18P—H18P | 111.4 |
C6D—C1D—C7D | 110.4 (19) | C20P—C18P—H18P | 111.4 |
C1D—C2D—C3D | 118 (2) | C18P—C19P—H19G | 109.5 |
C1D—C2D—C15D | 122 (3) | C18P—C19P—H19H | 109.5 |
C3D—C2D—C15D | 120 (3) | H19G—C19P—H19H | 109.5 |
C2D—C3D—C4D | 122 (3) | C18P—C19P—H19I | 109.5 |
C2D—C3D—H3D | 119.2 | H19G—C19P—H19I | 109.5 |
C4D—C3D—H3D | 119.2 | H19H—C19P—H19I | 109.5 |
C5D—C4D—C3D | 117 (2) | C18P—C20P—H20G | 109.5 |
C5D—C4D—C18D | 117 (3) | C18P—C20P—H20H | 109.5 |
C3D—C4D—C18D | 124 (3) | H20G—C20P—H20H | 109.5 |
C6D—C5D—C4D | 122 (3) | C18P—C20P—H20I | 109.5 |
C6D—C5D—H5D | 118.9 | H20G—C20P—H20I | 109.5 |
C4D—C5D—H5D | 118.9 | H20H—C20P—H20I | 109.5 |
C5D—C6D—C1D | 118 (2) | C6P—C21P—C22P | 109 (3) |
C5D—C6D—C21D | 134 (2) | C6P—C21P—C23P | 112 (4) |
C1D—C6D—C21D | 109 (2) | C22P—C21P—C23P | 113 (4) |
O1D—C7D—C22D | 110 (2) | C6P—C21P—H21P | 107.3 |
O1D—C7D—C8D | 111 (3) | C22P—C21P—H21P | 107.3 |
C22D—C7D—C8D | 112 (3) | C23P—C21P—H21P | 107.3 |
O1D—C7D—C1D | 108 (3) | C21P—C22P—H22F | 109.5 |
C22D—C7D—C1D | 102.5 (19) | C21P—C22P—H22G | 109.5 |
C8D—C7D—C1D | 113 (3) | H22F—C22P—H22G | 109.5 |
C13D—C8D—C9D | 119 (2) | C21P—C22P—H22H | 109.5 |
C13D—C8D—C7D | 123 (2) | H22F—C22P—H22H | 109.5 |
C9D—C8D—C7D | 118 (2) | H22G—C22P—H22H | 109.5 |
C8D—C9D—C10D | 119 (3) | C21P—C23P—H23G | 109.5 |
C8D—C9D—H9D | 120.3 | C21P—C23P—H23H | 109.5 |
C10D—C9D—H9D | 120.3 | H23G—C23P—H23H | 109.5 |
C11D—C10D—C9D | 122 (3) | C21P—C23P—H23I | 109.5 |
C11D—C10D—H10D | 119.1 | H23G—C23P—H23I | 109.5 |
C9D—C10D—H10D | 119.1 | H23H—C23P—H23I | 109.5 |
C31H39NO3 | Dx = 1.118 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 2213 reflections |
a = 6.3595 (5) Å | θ = 1.6–18.8° |
b = 13.5442 (11) Å | µ = 0.07 mm−1 |
c = 32.6718 (16) Å | T = 299 K |
V = 2814.2 (3) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.12 × 0.10 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 5439 independent reflections |
Radiation source: fine-focus sealed tube | 2046 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.124 |
ω scans | θmax = 26.0°, θmin = 1.6° |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | h = −7→7 |
Tmin = 0.812, Tmax = 1.000 | k = −14→16 |
25010 measured reflections | l = −40→40 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.096 | H-atom parameters constrained |
wR(F2) = 0.195 | w = 1/[σ2(Fo2) + (0.0334P)2 + 0.5481P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
5439 reflections | Δρmax = 0.12 e Å−3 |
498 parameters | Δρmin = −0.12 e Å−3 |
583 restraints | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −1.0 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 1.044 (4) | 0.2419 (17) | 0.6336 (9) | 0.079 (7) | 0.399 (4) |
O2 | 0.6471 (10) | 0.6317 (4) | 0.51770 (16) | 0.0813 (17) | 0.399 (4) |
O3 | 0.3432 (11) | 0.6162 (5) | 0.55003 (16) | 0.094 (2) | 0.399 (4) |
C1 | 0.818 (5) | 0.279 (2) | 0.6904 (6) | 0.051 (9)* | 0.399 (4) |
C2 | 0.863 (5) | 0.3448 (19) | 0.7221 (7) | 0.067 (9)* | 0.399 (4) |
C3 | 0.795 (5) | 0.327 (2) | 0.7624 (8) | 0.069 (8)* | 0.399 (4) |
H3 | 0.8216 | 0.3733 | 0.7829 | 0.083* | 0.399 (4) |
C4 | 0.688 (5) | 0.2391 (19) | 0.7713 (6) | 0.048 (7)* | 0.399 (4) |
C5 | 0.631 (5) | 0.1791 (18) | 0.7389 (6) | 0.054 (7)* | 0.399 (4) |
H5 | 0.5466 | 0.1243 | 0.7439 | 0.065* | 0.399 (4) |
C6 | 0.697 (5) | 0.1982 (18) | 0.6988 (6) | 0.063 (9)* | 0.399 (4) |
C7 | 0.910 (4) | 0.2946 (17) | 0.6481 (6) | 0.069 (8)* | 0.399 (4) |
C8 | 0.806 (4) | 0.3713 (14) | 0.6221 (6) | 0.053 (8)* | 0.399 (4) |
C9 | 0.920 (4) | 0.4060 (16) | 0.5898 (6) | 0.050 (7)* | 0.399 (4) |
H9 | 1.0548 | 0.3825 | 0.5845 | 0.060* | 0.399 (4) |
C10 | 0.829 (4) | 0.4772 (19) | 0.5651 (8) | 0.060 (8)* | 0.399 (4) |
H10 | 0.9065 | 0.5016 | 0.5432 | 0.072* | 0.399 (4) |
C11 | 0.631 (5) | 0.514 (2) | 0.5711 (9) | 0.056 (10)* | 0.399 (4) |
C12 | 0.520 (6) | 0.475 (3) | 0.6045 (12) | 0.058 (10)* | 0.399 (4) |
H12 | 0.3836 | 0.4957 | 0.6096 | 0.070* | 0.399 (4) |
C13 | 0.611 (5) | 0.405 (2) | 0.6298 (9) | 0.060 (9)* | 0.399 (4) |
H13 | 0.5364 | 0.3818 | 0.6523 | 0.072* | 0.399 (4) |
C14 | 0.5291 (15) | 0.5937 (6) | 0.5448 (2) | 0.070 (2) | 0.399 (4) |
C15 | 1.013 (4) | 0.4317 (18) | 0.7148 (10) | 0.074 (9)* | 0.399 (4) |
H15 | 1.0186 | 0.4416 | 0.6851 | 0.089* | 0.399 (4) |
C16 | 1.233 (5) | 0.413 (4) | 0.729 (2) | 0.087 (17)* | 0.399 (4) |
H16A | 1.2827 | 0.3524 | 0.7165 | 0.130* | 0.399 (4) |
H16B | 1.3215 | 0.4664 | 0.7200 | 0.130* | 0.399 (4) |
H16C | 1.2364 | 0.4073 | 0.7578 | 0.130* | 0.399 (4) |
C17 | 0.926 (5) | 0.527 (2) | 0.7330 (10) | 0.113 (11)* | 0.399 (4) |
H17A | 0.7841 | 0.5368 | 0.7236 | 0.169* | 0.399 (4) |
H17B | 0.9264 | 0.5224 | 0.7623 | 0.169* | 0.399 (4) |
H17C | 1.0114 | 0.5815 | 0.7245 | 0.169* | 0.399 (4) |
C18 | 0.638 (4) | 0.214 (2) | 0.8168 (6) | 0.073 (8)* | 0.399 (4) |
H18 | 0.6515 | 0.1417 | 0.8192 | 0.088* | 0.399 (4) |
C19 | 0.786 (4) | 0.257 (2) | 0.8481 (7) | 0.064 (7)* | 0.399 (4) |
H19A | 0.9283 | 0.2414 | 0.8408 | 0.096* | 0.399 (4) |
H19B | 0.7687 | 0.3274 | 0.8489 | 0.096* | 0.399 (4) |
H19C | 0.7548 | 0.2299 | 0.8746 | 0.096* | 0.399 (4) |
C20 | 0.419 (5) | 0.237 (3) | 0.8274 (13) | 0.108 (14)* | 0.399 (4) |
H20A | 0.3267 | 0.2087 | 0.8073 | 0.162* | 0.399 (4) |
H20B | 0.3867 | 0.2095 | 0.8538 | 0.162* | 0.399 (4) |
H20C | 0.4005 | 0.3070 | 0.8281 | 0.162* | 0.399 (4) |
C21 | 0.631 (4) | 0.1283 (17) | 0.6655 (7) | 0.069 (8)* | 0.399 (4) |
H21 | 0.6181 | 0.1654 | 0.6399 | 0.083* | 0.399 (4) |
C22 | 0.793 (4) | 0.0474 (18) | 0.6596 (8) | 0.091 (9)* | 0.399 (4) |
H22A | 0.7476 | 0.0037 | 0.6382 | 0.137* | 0.399 (4) |
H22B | 0.9256 | 0.0763 | 0.6523 | 0.137* | 0.399 (4) |
H22C | 0.8085 | 0.0109 | 0.6846 | 0.137* | 0.399 (4) |
C23 | 0.419 (4) | 0.076 (2) | 0.6745 (11) | 0.087 (10)* | 0.399 (4) |
H23A | 0.3847 | 0.0327 | 0.6523 | 0.130* | 0.399 (4) |
H23B | 0.4297 | 0.0391 | 0.6994 | 0.130* | 0.399 (4) |
H23C | 0.3099 | 0.1250 | 0.6773 | 0.130* | 0.399 (4) |
O1D | 1.093 (4) | 0.273 (3) | 0.6402 (12) | 0.069 (9) | 0.312 (4) |
O2D | 0.6471 (10) | 0.6317 (4) | 0.51770 (16) | 0.0813 (17) | 0.312 (4) |
O3D | 0.3432 (11) | 0.6162 (5) | 0.55003 (16) | 0.094 (2) | 0.312 (4) |
C1D | 0.800 (6) | 0.282 (2) | 0.6904 (8) | 0.059 (12)* | 0.312 (4) |
C2D | 0.898 (5) | 0.344 (2) | 0.7176 (8) | 0.056 (9)* | 0.312 (4) |
C3D | 0.847 (5) | 0.331 (2) | 0.7592 (8) | 0.064 (9)* | 0.312 (4) |
H3D | 0.9148 | 0.3703 | 0.7787 | 0.077* | 0.312 (4) |
C4D | 0.696 (7) | 0.261 (3) | 0.7724 (8) | 0.069 (11)* | 0.312 (4) |
C5D | 0.605 (9) | 0.198 (4) | 0.7430 (8) | 0.062 (10)* | 0.312 (4) |
H5D | 0.5083 | 0.1508 | 0.7509 | 0.075* | 0.312 (4) |
C6D | 0.661 (8) | 0.208 (3) | 0.7022 (8) | 0.054 (10)* | 0.312 (4) |
C7D | 0.865 (4) | 0.2739 (17) | 0.6441 (7) | 0.073 (10)* | 0.312 (4) |
C8D | 0.767 (4) | 0.3568 (16) | 0.6185 (7) | 0.050 (9)* | 0.312 (4) |
C9D | 0.866 (6) | 0.387 (3) | 0.5827 (10) | 0.061 (9)* | 0.312 (4) |
H9D | 0.9878 | 0.3542 | 0.5744 | 0.074* | 0.312 (4) |
C10D | 0.790 (6) | 0.462 (3) | 0.5594 (11) | 0.063 (10)* | 0.312 (4) |
H10D | 0.8642 | 0.4823 | 0.5364 | 0.075* | 0.312 (4) |
C11D | 0.602 (5) | 0.509 (3) | 0.5693 (11) | 0.052 (10)* | 0.312 (4) |
C12D | 0.494 (7) | 0.472 (4) | 0.6026 (15) | 0.069 (11)* | 0.312 (4) |
H12D | 0.3633 | 0.4988 | 0.6092 | 0.083* | 0.312 (4) |
C13D | 0.574 (5) | 0.397 (3) | 0.6261 (11) | 0.061 (10)* | 0.312 (4) |
H13D | 0.4940 | 0.3721 | 0.6478 | 0.073* | 0.312 (4) |
C14D | 0.5291 (15) | 0.5937 (6) | 0.5448 (2) | 0.070 (2) | 0.312 (4) |
C15D | 1.042 (5) | 0.427 (2) | 0.7041 (11) | 0.070 (10)* | 0.312 (4) |
H15D | 1.0709 | 0.4168 | 0.6749 | 0.084* | 0.312 (4) |
C16D | 1.247 (7) | 0.419 (5) | 0.726 (3) | 0.075 (19)* | 0.312 (4) |
H16D | 1.3374 | 0.4717 | 0.7172 | 0.112* | 0.312 (4) |
H16E | 1.2234 | 0.4239 | 0.7548 | 0.112* | 0.312 (4) |
H16F | 1.3108 | 0.3568 | 0.7196 | 0.112* | 0.312 (4) |
C17D | 0.936 (7) | 0.528 (2) | 0.7084 (12) | 0.070 (12)* | 0.312 (4) |
H17D | 0.8051 | 0.5274 | 0.6936 | 0.105* | 0.312 (4) |
H17E | 0.9091 | 0.5410 | 0.7367 | 0.105* | 0.312 (4) |
H17F | 1.0260 | 0.5779 | 0.6974 | 0.105* | 0.312 (4) |
C18D | 0.621 (6) | 0.238 (4) | 0.8167 (8) | 0.091 (12)* | 0.312 (4) |
H18D | 0.5913 | 0.1688 | 0.8107 | 0.109* | 0.312 (4) |
C19D | 0.767 (6) | 0.214 (2) | 0.8503 (9) | 0.092 (12)* | 0.312 (4) |
H19D | 0.9040 | 0.2009 | 0.8392 | 0.137* | 0.312 (4) |
H19E | 0.7755 | 0.2695 | 0.8687 | 0.137* | 0.312 (4) |
H19F | 0.7167 | 0.1575 | 0.8647 | 0.137* | 0.312 (4) |
C20D | 0.399 (6) | 0.262 (4) | 0.8257 (16) | 0.080 (14)* | 0.312 (4) |
H20D | 0.3258 | 0.2758 | 0.8006 | 0.121* | 0.312 (4) |
H20E | 0.3337 | 0.2071 | 0.8392 | 0.121* | 0.312 (4) |
H20F | 0.3925 | 0.3191 | 0.8432 | 0.121* | 0.312 (4) |
C21D | 0.595 (6) | 0.150 (3) | 0.6642 (10) | 0.086 (11)* | 0.312 (4) |
H21D | 0.4721 | 0.1829 | 0.6524 | 0.104* | 0.312 (4) |
C22D | 0.785 (4) | 0.1715 (17) | 0.6358 (8) | 0.095 (9)* | 0.312 (4) |
H22D | 0.8959 | 0.1238 | 0.6408 | 0.114* | 0.312 (4) |
H22E | 0.7422 | 0.1659 | 0.6074 | 0.114* | 0.312 (4) |
C23D | 0.543 (6) | 0.044 (2) | 0.6696 (10) | 0.110 (12)* | 0.312 (4) |
H23D | 0.5042 | 0.0160 | 0.6437 | 0.165* | 0.312 (4) |
H23E | 0.6625 | 0.0095 | 0.6804 | 0.165* | 0.312 (4) |
H23F | 0.4270 | 0.0378 | 0.6884 | 0.165* | 0.312 (4) |
O1P | 1.113 (7) | 0.306 (3) | 0.6514 (16) | 0.075 (10) | 0.169 (4) |
O2P | 0.6471 (10) | 0.6317 (4) | 0.51770 (16) | 0.0813 (17) | 0.169 (4) |
O3P | 0.3432 (11) | 0.6162 (5) | 0.55003 (16) | 0.094 (2) | 0.169 (4) |
C1P | 0.807 (7) | 0.293 (3) | 0.7006 (10) | 0.053 (12)* | 0.169 (4) |
C2P | 0.874 (7) | 0.346 (3) | 0.7350 (10) | 0.062 (12)* | 0.169 (4) |
C3P | 0.795 (8) | 0.323 (4) | 0.7737 (11) | 0.063 (13)* | 0.169 (4) |
H3P | 0.8416 | 0.3564 | 0.7969 | 0.075* | 0.169 (4) |
C4P | 0.645 (8) | 0.250 (4) | 0.7764 (11) | 0.066 (14)* | 0.169 (4) |
C5P | 0.585 (13) | 0.193 (6) | 0.7434 (12) | 0.060 (13)* | 0.169 (4) |
H5P | 0.4929 | 0.1399 | 0.7468 | 0.072* | 0.169 (4) |
C6P | 0.664 (11) | 0.216 (4) | 0.7047 (12) | 0.056 (13)* | 0.169 (4) |
C7P | 0.938 (5) | 0.352 (2) | 0.6700 (8) | 0.059 (10)* | 0.169 (4) |
C8P | 0.828 (5) | 0.406 (3) | 0.6351 (10) | 0.054 (10)* | 0.169 (4) |
C9P | 0.945 (5) | 0.451 (3) | 0.6048 (10) | 0.065 (11)* | 0.169 (4) |
H9P | 1.0900 | 0.4410 | 0.6040 | 0.078* | 0.169 (4) |
C10P | 0.851 (6) | 0.511 (3) | 0.5752 (11) | 0.069 (12)* | 0.169 (4) |
H10P | 0.9321 | 0.5369 | 0.5543 | 0.082* | 0.169 (4) |
C11P | 0.639 (6) | 0.531 (3) | 0.5767 (10) | 0.065 (14)* | 0.169 (4) |
C12P | 0.520 (7) | 0.492 (5) | 0.6087 (16) | 0.063 (13)* | 0.169 (4) |
H12P | 0.3778 | 0.5075 | 0.6111 | 0.076* | 0.169 (4) |
C13P | 0.616 (6) | 0.430 (4) | 0.6370 (15) | 0.056 (12)* | 0.169 (4) |
H13P | 0.5349 | 0.4042 | 0.6581 | 0.067* | 0.169 (4) |
C14P | 0.5291 (15) | 0.5937 (6) | 0.5448 (2) | 0.070 (2) | 0.169 (4) |
C15P | 0.989 (6) | 0.422 (3) | 0.7097 (11) | 0.071 (14)* | 0.169 (4) |
C16P | 1.224 (7) | 0.438 (5) | 0.7127 (18) | 0.10 (2)* | 0.169 (4) |
H16G | 1.2657 | 0.4891 | 0.6942 | 0.154* | 0.169 (4) |
H16H | 1.2600 | 0.4563 | 0.7402 | 0.154* | 0.169 (4) |
H16I | 1.2954 | 0.3776 | 0.7057 | 0.154* | 0.169 (4) |
C17P | 0.884 (10) | 0.523 (3) | 0.713 (2) | 0.061 (19)* | 0.169 (4) |
H17G | 0.9604 | 0.5701 | 0.6968 | 0.092* | 0.169 (4) |
H17H | 0.7419 | 0.5190 | 0.7036 | 0.092* | 0.169 (4) |
H17I | 0.8850 | 0.5442 | 0.7412 | 0.092* | 0.169 (4) |
C18P | 0.555 (7) | 0.219 (4) | 0.8176 (11) | 0.074 (13)* | 0.169 (4) |
H18P | 0.5577 | 0.1473 | 0.8212 | 0.089* | 0.169 (4) |
C19P | 0.681 (8) | 0.271 (5) | 0.8508 (14) | 0.087 (18)* | 0.169 (4) |
H19G | 0.8216 | 0.2452 | 0.8512 | 0.130* | 0.169 (4) |
H19H | 0.6858 | 0.3407 | 0.8451 | 0.130* | 0.169 (4) |
H19I | 0.6157 | 0.2605 | 0.8769 | 0.130* | 0.169 (4) |
C20P | 0.331 (6) | 0.258 (5) | 0.8157 (16) | 0.065 (16)* | 0.169 (4) |
H20G | 0.2553 | 0.2237 | 0.7946 | 0.097* | 0.169 (4) |
H20H | 0.2629 | 0.2470 | 0.8416 | 0.097* | 0.169 (4) |
H20I | 0.3330 | 0.3273 | 0.8098 | 0.097* | 0.169 (4) |
C21P | 0.581 (8) | 0.154 (4) | 0.6698 (15) | 0.080 (14)* | 0.169 (4) |
H21P | 0.5461 | 0.1983 | 0.6471 | 0.096* | 0.169 (4) |
C22P | 0.755 (9) | 0.084 (4) | 0.6548 (17) | 0.077 (17)* | 0.169 (4) |
H22F | 0.7026 | 0.0444 | 0.6327 | 0.115* | 0.169 (4) |
H22G | 0.8732 | 0.1220 | 0.6455 | 0.115* | 0.169 (4) |
H22H | 0.7984 | 0.0418 | 0.6769 | 0.115* | 0.169 (4) |
C23P | 0.384 (9) | 0.095 (5) | 0.680 (3) | 0.11 (3)* | 0.169 (4) |
H23G | 0.3404 | 0.0574 | 0.6571 | 0.158* | 0.169 (4) |
H23H | 0.4133 | 0.0515 | 0.7028 | 0.158* | 0.169 (4) |
H23I | 0.2735 | 0.1399 | 0.6881 | 0.158* | 0.169 (4) |
O1Z | 1.110 (8) | 0.281 (6) | 0.652 (2) | 0.073 (11)* | 0.121 (4) |
O2Z | 0.6471 (10) | 0.6317 (4) | 0.51770 (16) | 0.0813 (17) | 0.121 (4) |
O3Z | 0.3432 (11) | 0.6162 (5) | 0.55003 (16) | 0.094 (2) | 0.121 (4) |
C1Z | 0.876 (7) | 0.303 (3) | 0.6989 (11) | 0.048 (13)* | 0.121 (4) |
C2Z | 0.914 (6) | 0.370 (3) | 0.7300 (12) | 0.061 (14)* | 0.121 (4) |
C3Z | 0.836 (7) | 0.359 (3) | 0.7692 (13) | 0.079 (15)* | 0.121 (4) |
H3Z | 0.8604 | 0.4061 | 0.7893 | 0.095* | 0.121 (4) |
C4Z | 0.721 (8) | 0.275 (4) | 0.7776 (11) | 0.059 (14)* | 0.121 (4) |
C5Z | 0.672 (9) | 0.209 (4) | 0.7464 (11) | 0.061 (14)* | 0.121 (4) |
H5Z | 0.5826 | 0.1561 | 0.7520 | 0.074* | 0.121 (4) |
C6Z | 0.753 (8) | 0.220 (3) | 0.7067 (11) | 0.055 (13)* | 0.121 (4) |
C7Z | 0.887 (8) | 0.288 (3) | 0.6529 (11) | 0.074 (15)* | 0.121 (4) |
C8Z | 0.792 (10) | 0.365 (4) | 0.6237 (15) | 0.054 (15)* | 0.121 (4) |
C9Z | 0.884 (14) | 0.384 (7) | 0.586 (2) | 0.060 (15)* | 0.121 (4) |
H9Z | 1.0046 | 0.3498 | 0.5779 | 0.072* | 0.121 (4) |
C10Z | 0.796 (14) | 0.453 (6) | 0.560 (2) | 0.066 (15)* | 0.121 (4) |
H10Z | 0.8494 | 0.4608 | 0.5333 | 0.079* | 0.121 (4) |
C11Z | 0.630 (6) | 0.5113 (18) | 0.5723 (12) | 0.057 (15)* | 0.121 (4) |
C12Z | 0.542 (10) | 0.496 (5) | 0.6110 (16) | 0.061 (14)* | 0.121 (4) |
H12Z | 0.4274 | 0.5337 | 0.6195 | 0.073* | 0.121 (4) |
C13Z | 0.629 (11) | 0.425 (6) | 0.6367 (18) | 0.058 (14)* | 0.121 (4) |
H13Z | 0.5758 | 0.4177 | 0.6630 | 0.069* | 0.121 (4) |
C14Z | 0.5291 (15) | 0.5937 (6) | 0.5448 (2) | 0.070 (2) | 0.121 (4) |
C15Z | 1.045 (8) | 0.458 (3) | 0.7199 (19) | 0.069 (14)* | 0.121 (4) |
H15Z | 1.0766 | 0.4512 | 0.6907 | 0.083* | 0.121 (4) |
C16Z | 1.253 (7) | 0.453 (5) | 0.740 (2) | 0.11 (3)* | 0.121 (4) |
H16J | 1.3128 | 0.3892 | 0.7361 | 0.164* | 0.121 (4) |
H16K | 1.3441 | 0.5027 | 0.7288 | 0.164* | 0.121 (4) |
H16L | 1.2359 | 0.4653 | 0.7690 | 0.164* | 0.121 (4) |
C17Z | 0.925 (11) | 0.552 (4) | 0.723 (3) | 0.07 (2)* | 0.121 (4) |
H17J | 0.7943 | 0.5453 | 0.7082 | 0.105* | 0.121 (4) |
H17K | 0.8975 | 0.5672 | 0.7508 | 0.105* | 0.121 (4) |
H17L | 1.0057 | 0.6045 | 0.7106 | 0.105* | 0.121 (4) |
C18Z | 0.628 (9) | 0.267 (4) | 0.8200 (12) | 0.082 (15)* | 0.121 (4) |
H18Z | 0.6132 | 0.1967 | 0.8273 | 0.098* | 0.121 (4) |
C19Z | 0.808 (10) | 0.311 (6) | 0.8440 (17) | 0.09 (2)* | 0.121 (4) |
H19J | 0.7733 | 0.3120 | 0.8726 | 0.138* | 0.121 (4) |
H19K | 0.9327 | 0.2730 | 0.8398 | 0.138* | 0.121 (4) |
H19L | 0.8316 | 0.3779 | 0.8348 | 0.138* | 0.121 (4) |
C20Z | 0.422 (10) | 0.319 (6) | 0.828 (2) | 0.11 (2)* | 0.121 (4) |
H20J | 0.3800 | 0.3081 | 0.8561 | 0.166* | 0.121 (4) |
H20K | 0.4397 | 0.3889 | 0.8237 | 0.166* | 0.121 (4) |
H20L | 0.3155 | 0.2944 | 0.8101 | 0.166* | 0.121 (4) |
C21Z | 0.765 (7) | 0.183 (3) | 0.6633 (11) | 0.085 (14)* | 0.121 (4) |
C22Z | 0.908 (10) | 0.093 (3) | 0.6622 (18) | 0.082 (19)* | 0.121 (4) |
H22I | 0.9169 | 0.0686 | 0.6347 | 0.123* | 0.121 (4) |
H22J | 1.0456 | 0.1109 | 0.6717 | 0.123* | 0.121 (4) |
H22K | 0.8509 | 0.0425 | 0.6796 | 0.123* | 0.121 (4) |
C23Z | 0.565 (10) | 0.171 (5) | 0.638 (2) | 0.15 (3)* | 0.121 (4) |
H23J | 0.6007 | 0.1473 | 0.6113 | 0.221* | 0.121 (4) |
H23K | 0.4733 | 0.1251 | 0.6514 | 0.221* | 0.121 (4) |
H23L | 0.4959 | 0.2340 | 0.6357 | 0.221* | 0.121 (4) |
N1 | 0.0554 (10) | 0.6670 (4) | 0.49226 (16) | 0.0682 (19) | |
H1A | 0.1547 | 0.6434 | 0.5088 | 0.082* | |
H1B | −0.0707 | 0.6521 | 0.5023 | 0.082* | |
H1C | 0.0682 | 0.7323 | 0.4904 | 0.082* | |
C24 | 0.2920 (15) | 0.6528 (7) | 0.4332 (2) | 0.102 (3) | |
H24A | 0.4004 | 0.6372 | 0.4526 | 0.152* | |
H24B | 0.2914 | 0.7226 | 0.4281 | 0.152* | |
H24C | 0.3183 | 0.6182 | 0.4080 | 0.152* | |
C25 | 0.0792 (14) | 0.6215 (7) | 0.4503 (2) | 0.074 (3) | |
H25 | −0.0311 | 0.6482 | 0.4325 | 0.089* | |
C26 | 0.050 (2) | 0.5132 (8) | 0.4532 (3) | 0.083 (3) | |
C27 | −0.137 (2) | 0.4721 (10) | 0.4401 (3) | 0.114 (4) | |
H27 | −0.2436 | 0.5132 | 0.4305 | 0.137* | |
C28 | −0.169 (3) | 0.3705 (14) | 0.4409 (4) | 0.148 (6) | |
H28 | −0.2955 | 0.3434 | 0.4319 | 0.178* | |
C29 | −0.013 (4) | 0.3122 (14) | 0.4550 (6) | 0.171 (8) | |
H29 | −0.0350 | 0.2443 | 0.4554 | 0.205* | |
C30 | 0.173 (4) | 0.3476 (12) | 0.4685 (5) | 0.172 (7) | |
H30 | 0.2776 | 0.3053 | 0.4777 | 0.206* | |
C31 | 0.202 (2) | 0.4506 (10) | 0.4681 (3) | 0.120 (4) | |
H31 | 0.3269 | 0.4768 | 0.4782 | 0.145* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.095 (13) | 0.063 (14) | 0.080 (12) | 0.028 (11) | 0.026 (11) | 0.015 (11) |
O2 | 0.083 (4) | 0.090 (4) | 0.071 (3) | −0.001 (4) | 0.010 (3) | 0.030 (3) |
O3 | 0.076 (4) | 0.140 (5) | 0.066 (4) | 0.023 (4) | −0.007 (4) | 0.034 (4) |
C14 | 0.084 (6) | 0.076 (5) | 0.051 (5) | 0.000 (5) | −0.021 (5) | 0.008 (4) |
O1D | 0.071 (13) | 0.062 (18) | 0.074 (15) | 0.011 (13) | 0.011 (13) | −0.007 (14) |
O2D | 0.083 (4) | 0.090 (4) | 0.071 (3) | −0.001 (4) | 0.010 (3) | 0.030 (3) |
O3D | 0.076 (4) | 0.140 (5) | 0.066 (4) | 0.023 (4) | −0.007 (4) | 0.034 (4) |
C14D | 0.084 (6) | 0.076 (5) | 0.051 (5) | 0.000 (5) | −0.021 (5) | 0.008 (4) |
O1P | 0.077 (15) | 0.073 (18) | 0.074 (17) | 0.012 (15) | 0.018 (14) | 0.008 (15) |
O2P | 0.083 (4) | 0.090 (4) | 0.071 (3) | −0.001 (4) | 0.010 (3) | 0.030 (3) |
O3P | 0.076 (4) | 0.140 (5) | 0.066 (4) | 0.023 (4) | −0.007 (4) | 0.034 (4) |
C14P | 0.084 (6) | 0.076 (5) | 0.051 (5) | 0.000 (5) | −0.021 (5) | 0.008 (4) |
O2Z | 0.083 (4) | 0.090 (4) | 0.071 (3) | −0.001 (4) | 0.010 (3) | 0.030 (3) |
O3Z | 0.076 (4) | 0.140 (5) | 0.066 (4) | 0.023 (4) | −0.007 (4) | 0.034 (4) |
C14Z | 0.084 (6) | 0.076 (5) | 0.051 (5) | 0.000 (5) | −0.021 (5) | 0.008 (4) |
N1 | 0.073 (5) | 0.081 (4) | 0.051 (4) | 0.006 (4) | −0.002 (4) | 0.016 (3) |
C24 | 0.109 (9) | 0.127 (8) | 0.068 (6) | −0.005 (7) | 0.031 (6) | −0.002 (6) |
C25 | 0.071 (7) | 0.105 (8) | 0.046 (5) | −0.002 (6) | −0.011 (5) | 0.008 (5) |
C26 | 0.106 (9) | 0.093 (8) | 0.050 (5) | −0.007 (8) | 0.006 (6) | −0.006 (6) |
C27 | 0.130 (13) | 0.116 (11) | 0.095 (8) | −0.004 (9) | 0.024 (8) | −0.014 (7) |
C28 | 0.155 (16) | 0.156 (17) | 0.133 (12) | −0.036 (13) | 0.042 (11) | −0.035 (12) |
C29 | 0.24 (3) | 0.116 (15) | 0.159 (16) | −0.037 (16) | 0.036 (17) | −0.017 (11) |
C30 | 0.24 (2) | 0.103 (14) | 0.171 (14) | 0.033 (13) | −0.016 (14) | 0.007 (10) |
C31 | 0.165 (13) | 0.105 (10) | 0.091 (8) | 0.010 (10) | −0.027 (8) | −0.006 (7) |
O1—C7 | 1.21 (2) | C4P—C18P | 1.52 (2) |
O2—C14 | 1.269 (9) | C5P—C6P | 1.40 (2) |
O3—C14 | 1.232 (9) | C5P—H5P | 0.9300 |
C1—C6 | 1.370 (19) | C6P—C21P | 1.51 (2) |
C1—C2 | 1.39 (2) | C7P—C8P | 1.53 (2) |
C1—C7 | 1.516 (19) | C7P—C15P | 1.64 (2) |
C2—C3 | 1.40 (2) | C8P—C9P | 1.38 (2) |
C2—C15 | 1.53 (2) | C8P—C13P | 1.39 (2) |
C3—C4 | 1.41 (2) | C9P—C10P | 1.40 (2) |
C3—H3 | 0.9300 | C9P—H9P | 0.9300 |
C4—C5 | 1.38 (2) | C10P—C11P | 1.38 (2) |
C4—C18 | 1.559 (19) | C10P—H10P | 0.9300 |
C5—C6 | 1.400 (19) | C11P—C12P | 1.40 (2) |
C5—H5 | 0.9300 | C11P—C14P | 1.51 (2) |
C6—C21 | 1.50 (2) | C12P—C13P | 1.39 (2) |
C7—C8 | 1.496 (18) | C12P—H12P | 0.9300 |
C8—C13 | 1.35 (2) | C13P—H13P | 0.9300 |
C8—C9 | 1.364 (18) | C15P—C16P | 1.51 (3) |
C9—C10 | 1.386 (18) | C15P—C17P | 1.53 (2) |
C9—H9 | 0.9300 | C16P—H16G | 0.9600 |
C10—C11 | 1.36 (2) | C16P—H16H | 0.9600 |
C10—H10 | 0.9300 | C16P—H16I | 0.9600 |
C11—C12 | 1.40 (2) | C17P—H17G | 0.9600 |
C11—C14 | 1.527 (17) | C17P—H17H | 0.9600 |
C12—C13 | 1.38 (2) | C17P—H17I | 0.9600 |
C12—H12 | 0.9300 | C18P—C20P | 1.52 (3) |
C13—H13 | 0.9300 | C18P—C19P | 1.52 (3) |
C15—C16 | 1.49 (2) | C18P—H18P | 0.9800 |
C15—C17 | 1.52 (2) | C19P—H19G | 0.9600 |
C15—H15 | 0.9800 | C19P—H19H | 0.9600 |
C16—H16A | 0.9600 | C19P—H19I | 0.9600 |
C16—H16B | 0.9600 | C20P—H20G | 0.9600 |
C16—H16C | 0.9600 | C20P—H20H | 0.9600 |
C17—H17A | 0.9600 | C20P—H20I | 0.9600 |
C17—H17B | 0.9600 | C21P—C23P | 1.53 (3) |
C17—H17C | 0.9600 | C21P—C22P | 1.53 (3) |
C18—C20 | 1.47 (2) | C21P—H21P | 0.9800 |
C18—C19 | 1.51 (2) | C22P—H22F | 0.9600 |
C18—H18 | 0.9800 | C22P—H22G | 0.9600 |
C19—H19A | 0.9600 | C22P—H22H | 0.9600 |
C19—H19B | 0.9600 | C23P—H23G | 0.9600 |
C19—H19C | 0.9600 | C23P—H23H | 0.9600 |
C20—H20A | 0.9600 | C23P—H23I | 0.9600 |
C20—H20B | 0.9600 | O1Z—C7Z | 1.42 (3) |
C20—H20C | 0.9600 | O2Z—C14Z | 1.269 (9) |
C21—C22 | 1.52 (2) | O3Z—C14Z | 1.232 (9) |
C21—C23 | 1.55 (2) | C1Z—C2Z | 1.38 (2) |
C21—H21 | 0.9800 | C1Z—C6Z | 1.40 (2) |
C22—H22A | 0.9600 | C1Z—C7Z | 1.52 (2) |
C22—H22B | 0.9600 | C2Z—C3Z | 1.38 (2) |
C22—H22C | 0.9600 | C2Z—C15Z | 1.50 (2) |
C23—H23A | 0.9600 | C3Z—C4Z | 1.38 (3) |
C23—H23B | 0.9600 | C3Z—H3Z | 0.9300 |
C23—H23C | 0.9600 | C4Z—C5Z | 1.39 (2) |
O1D—C7D | 1.46 (2) | C4Z—C18Z | 1.51 (2) |
O2D—C14D | 1.269 (9) | C5Z—C6Z | 1.40 (2) |
O3D—C14D | 1.232 (9) | C5Z—H5Z | 0.9300 |
C1D—C2D | 1.37 (2) | C6Z—C21Z | 1.51 (2) |
C1D—C6D | 1.39 (2) | C7Z—C8Z | 1.54 (2) |
C1D—C7D | 1.57 (2) | C7Z—C21Z | 1.65 (2) |
C2D—C3D | 1.41 (2) | C8Z—C13Z | 1.39 (3) |
C2D—C15D | 1.52 (2) | C8Z—C9Z | 1.39 (2) |
C3D—C4D | 1.42 (2) | C9Z—C10Z | 1.39 (3) |
C3D—H3D | 0.9300 | C9Z—H9Z | 0.9300 |
C4D—C5D | 1.40 (2) | C10Z—C11Z | 1.38 (2) |
C4D—C18D | 1.55 (2) | C10Z—H10Z | 0.9300 |
C5D—C6D | 1.39 (2) | C11Z—C12Z | 1.40 (2) |
C5D—H5D | 0.9300 | C11Z—C14Z | 1.57 (2) |
C6D—C21D | 1.53 (2) | C12Z—C13Z | 1.39 (3) |
C7D—C22D | 1.50 (2) | C12Z—H12Z | 0.9300 |
C7D—C8D | 1.53 (2) | C13Z—H13Z | 0.9300 |
C8D—C13D | 1.36 (2) | C15Z—C16Z | 1.48 (3) |
C8D—C9D | 1.39 (2) | C15Z—C17Z | 1.48 (3) |
C9D—C10D | 1.36 (2) | C15Z—H15Z | 0.9800 |
C9D—H9D | 0.9300 | C16Z—H16J | 0.9600 |
C10D—C11D | 1.39 (2) | C16Z—H16K | 0.9600 |
C10D—H10D | 0.9300 | C16Z—H16L | 0.9600 |
C11D—C12D | 1.38 (2) | C17Z—H17J | 0.9600 |
C11D—C14D | 1.470 (18) | C17Z—H17K | 0.9600 |
C12D—C13D | 1.38 (2) | C17Z—H17L | 0.9600 |
C12D—H12D | 0.9300 | C18Z—C20Z | 1.51 (3) |
C13D—H13D | 0.9300 | C18Z—C19Z | 1.52 (3) |
C15D—C16D | 1.48 (2) | C18Z—H18Z | 0.9800 |
C15D—C17D | 1.53 (2) | C19Z—H19J | 0.9600 |
C15D—H15D | 0.9800 | C19Z—H19K | 0.9600 |
C16D—H16D | 0.9600 | C19Z—H19L | 0.9600 |
C16D—H16E | 0.9600 | C20Z—H20J | 0.9600 |
C16D—H16F | 0.9600 | C20Z—H20K | 0.9600 |
C17D—H17D | 0.9600 | C20Z—H20L | 0.9600 |
C17D—H17E | 0.9600 | C21Z—C23Z | 1.52 (2) |
C17D—H17F | 0.9600 | C21Z—C22Z | 1.53 (3) |
C18D—C19D | 1.47 (2) | C22Z—H22I | 0.9600 |
C18D—C20D | 1.48 (2) | C22Z—H22J | 0.9600 |
C18D—H18D | 0.9800 | C22Z—H22K | 0.9600 |
C19D—H19D | 0.9600 | C23Z—H23J | 0.9600 |
C19D—H19E | 0.9600 | C23Z—H23K | 0.9600 |
C19D—H19F | 0.9600 | C23Z—H23L | 0.9600 |
C20D—H20D | 0.9600 | N1—C25 | 1.510 (9) |
C20D—H20E | 0.9600 | N1—H1A | 0.8900 |
C20D—H20F | 0.9600 | N1—H1B | 0.8900 |
C21D—C23D | 1.49 (2) | N1—H1C | 0.8900 |
C21D—C22D | 1.55 (2) | C24—C25 | 1.525 (11) |
C21D—H21D | 0.9800 | C24—H24A | 0.9600 |
C22D—H22D | 0.9700 | C24—H24B | 0.9600 |
C22D—H22E | 0.9700 | C24—H24C | 0.9600 |
C23D—H23D | 0.9600 | C25—C26 | 1.482 (12) |
C23D—H23E | 0.9600 | C25—H25 | 0.9800 |
C23D—H23F | 0.9600 | C26—C31 | 1.374 (14) |
O1P—C7P | 1.41 (2) | C26—C27 | 1.384 (15) |
O2P—C14P | 1.269 (9) | C27—C28 | 1.392 (16) |
O3P—C14P | 1.232 (9) | C27—H27 | 0.9300 |
C1P—C6P | 1.39 (2) | C28—C29 | 1.35 (2) |
C1P—C2P | 1.40 (2) | C28—H28 | 0.9300 |
C1P—C7P | 1.52 (2) | C29—C30 | 1.35 (2) |
C2P—C3P | 1.40 (2) | C29—H29 | 0.9300 |
C2P—C15P | 1.51 (2) | C30—C31 | 1.408 (16) |
C3P—C4P | 1.38 (2) | C30—H30 | 0.9300 |
C3P—H3P | 0.9300 | C31—H31 | 0.9300 |
C4P—C5P | 1.38 (2) | ||
C6—C1—C2 | 118.5 (17) | C1P—C7P—C8P | 119 (2) |
C6—C1—C7 | 120.6 (19) | O1P—C7P—C15P | 116 (3) |
C2—C1—C7 | 120.8 (19) | C1P—C7P—C15P | 83.6 (17) |
C1—C2—C3 | 121.8 (19) | C8P—C7P—C15P | 113 (2) |
C1—C2—C15 | 120 (2) | C9P—C8P—C13P | 117 (2) |
C3—C2—C15 | 117.8 (19) | C9P—C8P—C7P | 120 (2) |
C2—C3—C4 | 119 (2) | C13P—C8P—C7P | 122 (2) |
C2—C3—H3 | 120.5 | C8P—C9P—C10P | 121 (3) |
C4—C3—H3 | 120.5 | C8P—C9P—H9P | 119.5 |
C5—C4—C3 | 117.9 (18) | C10P—C9P—H9P | 119.5 |
C5—C4—C18 | 123.1 (18) | C11P—C10P—C9P | 121 (3) |
C3—C4—C18 | 119.0 (18) | C11P—C10P—H10P | 119.5 |
C4—C5—C6 | 122.0 (19) | C9P—C10P—H10P | 119.5 |
C4—C5—H5 | 119.0 | C10P—C11P—C12P | 119 (2) |
C6—C5—H5 | 119.0 | C10P—C11P—C14P | 123 (3) |
C1—C6—C5 | 120.1 (18) | C12P—C11P—C14P | 119 (3) |
C1—C6—C21 | 121.2 (18) | C13P—C12P—C11P | 119 (3) |
C5—C6—C21 | 118.6 (18) | C13P—C12P—H12P | 120.4 |
O1—C7—C8 | 120 (2) | C11P—C12P—H12P | 120.4 |
O1—C7—C1 | 123 (2) | C12P—C13P—C8P | 123 (3) |
C8—C7—C1 | 116.2 (19) | C12P—C13P—H13P | 118.7 |
C13—C8—C9 | 121.0 (18) | C8P—C13P—H13P | 118.7 |
C13—C8—C7 | 122.6 (19) | O3P—C14P—O2P | 124.3 (7) |
C9—C8—C7 | 116.3 (18) | O3P—C14P—C11P | 119.0 (16) |
C8—C9—C10 | 117.9 (19) | O2P—C14P—C11P | 115.7 (16) |
C8—C9—H9 | 121.1 | C2P—C15P—C16P | 123 (3) |
C10—C9—H9 | 121.1 | C2P—C15P—C17P | 111 (3) |
C11—C10—C9 | 124 (2) | C16P—C15P—C17P | 107 (3) |
C11—C10—H10 | 118.1 | C2P—C15P—C7P | 86.6 (18) |
C9—C10—H10 | 118.1 | C16P—C15P—C7P | 109 (3) |
C10—C11—C12 | 115.9 (18) | C17P—C15P—C7P | 120 (3) |
C10—C11—C14 | 124.6 (19) | C15P—C16P—H16G | 109.5 |
C12—C11—C14 | 119.5 (19) | C15P—C16P—H16H | 109.5 |
C13—C12—C11 | 121 (2) | H16G—C16P—H16H | 109.5 |
C13—C12—H12 | 119.5 | C15P—C16P—H16I | 109.5 |
C11—C12—H12 | 119.5 | H16G—C16P—H16I | 109.5 |
C8—C13—C12 | 120 (2) | H16H—C16P—H16I | 109.5 |
C8—C13—H13 | 119.8 | C15P—C17P—H17G | 109.5 |
C12—C13—H13 | 119.8 | C15P—C17P—H17H | 109.5 |
O3—C14—O2 | 124.3 (7) | H17G—C17P—H17H | 109.5 |
O3—C14—C11 | 120.3 (13) | C15P—C17P—H17I | 109.5 |
O2—C14—C11 | 115.4 (13) | H17G—C17P—H17I | 109.5 |
C16—C15—C17 | 112 (3) | H17H—C17P—H17I | 109.5 |
C16—C15—C2 | 114 (2) | C20P—C18P—C19P | 111 (3) |
C17—C15—C2 | 111 (2) | C20P—C18P—C4P | 103 (3) |
C16—C15—H15 | 106.5 | C19P—C18P—C4P | 108 (3) |
C17—C15—H15 | 106.5 | C20P—C18P—H18P | 111.4 |
C2—C15—H15 | 106.5 | C19P—C18P—H18P | 111.4 |
C15—C16—H16A | 109.5 | C4P—C18P—H18P | 111.4 |
C15—C16—H16B | 109.5 | C18P—C19P—H19G | 109.5 |
H16A—C16—H16B | 109.5 | C18P—C19P—H19H | 109.5 |
C15—C16—H16C | 109.5 | H19G—C19P—H19H | 109.5 |
H16A—C16—H16C | 109.5 | C18P—C19P—H19I | 109.5 |
H16B—C16—H16C | 109.5 | H19G—C19P—H19I | 109.5 |
C15—C17—H17A | 109.5 | H19H—C19P—H19I | 109.5 |
C15—C17—H17B | 109.5 | C18P—C20P—H20G | 109.5 |
H17A—C17—H17B | 109.5 | C18P—C20P—H20H | 109.5 |
C15—C17—H17C | 109.5 | H20G—C20P—H20H | 109.5 |
H17A—C17—H17C | 109.5 | C18P—C20P—H20I | 109.5 |
H17B—C17—H17C | 109.5 | H20G—C20P—H20I | 109.5 |
C20—C18—C19 | 110 (2) | H20H—C20P—H20I | 109.5 |
C20—C18—C4 | 112 (2) | C6P—C21P—C23P | 114 (3) |
C19—C18—C4 | 115.6 (19) | C6P—C21P—C22P | 110 (3) |
C20—C18—H18 | 106.1 | C23P—C21P—C22P | 110 (3) |
C19—C18—H18 | 106.1 | C6P—C21P—H21P | 107.7 |
C4—C18—H18 | 106.1 | C23P—C21P—H21P | 107.7 |
C18—C19—H19A | 109.5 | C22P—C21P—H21P | 107.7 |
C18—C19—H19B | 109.5 | C21P—C22P—H22F | 109.5 |
H19A—C19—H19B | 109.5 | C21P—C22P—H22G | 109.5 |
C18—C19—H19C | 109.5 | H22F—C22P—H22G | 109.5 |
H19A—C19—H19C | 109.5 | C21P—C22P—H22H | 109.5 |
H19B—C19—H19C | 109.5 | H22F—C22P—H22H | 109.5 |
C18—C20—H20A | 109.5 | H22G—C22P—H22H | 109.5 |
C18—C20—H20B | 109.5 | C21P—C23P—H23G | 109.5 |
H20A—C20—H20B | 109.5 | C21P—C23P—H23H | 109.5 |
C18—C20—H20C | 109.5 | H23G—C23P—H23H | 109.5 |
H20A—C20—H20C | 109.5 | C21P—C23P—H23I | 109.5 |
H20B—C20—H20C | 109.5 | H23G—C23P—H23I | 109.5 |
C6—C21—C22 | 111 (2) | H23H—C23P—H23I | 109.5 |
C6—C21—C23 | 113 (2) | C2Z—C1Z—C6Z | 119 (2) |
C22—C21—C23 | 106.7 (19) | C2Z—C1Z—C7Z | 144 (3) |
C6—C21—H21 | 108.6 | C6Z—C1Z—C7Z | 95 (2) |
C22—C21—H21 | 108.6 | C1Z—C2Z—C3Z | 123 (3) |
C23—C21—H21 | 108.6 | C1Z—C2Z—C15Z | 117 (3) |
C21—C22—H22A | 109.5 | C3Z—C2Z—C15Z | 120 (3) |
C21—C22—H22B | 109.5 | C4Z—C3Z—C2Z | 118 (3) |
H22A—C22—H22B | 109.5 | C4Z—C3Z—H3Z | 121.2 |
C21—C22—H22C | 109.5 | C2Z—C3Z—H3Z | 121.2 |
H22A—C22—H22C | 109.5 | C3Z—C4Z—C5Z | 120 (3) |
H22B—C22—H22C | 109.5 | C3Z—C4Z—C18Z | 117 (3) |
C21—C23—H23A | 109.5 | C5Z—C4Z—C18Z | 122 (3) |
C21—C23—H23B | 109.5 | C4Z—C5Z—C6Z | 121 (3) |
H23A—C23—H23B | 109.5 | C4Z—C5Z—H5Z | 119.3 |
C21—C23—H23C | 109.5 | C6Z—C5Z—H5Z | 119.3 |
H23A—C23—H23C | 109.5 | C1Z—C6Z—C5Z | 118 (3) |
H23B—C23—H23C | 109.5 | C1Z—C6Z—C21Z | 94 (2) |
C2D—C1D—C6D | 123 (2) | C5Z—C6Z—C21Z | 148 (3) |
C2D—C1D—C7D | 123 (2) | O1Z—C7Z—C1Z | 95 (3) |
C6D—C1D—C7D | 112.6 (18) | O1Z—C7Z—C8Z | 115 (3) |
C1D—C2D—C3D | 117 (2) | C1Z—C7Z—C8Z | 120 (3) |
C1D—C2D—C15D | 123 (2) | O1Z—C7Z—C21Z | 115 (3) |
C3D—C2D—C15D | 121 (2) | C1Z—C7Z—C21Z | 83.9 (18) |
C2D—C3D—C4D | 122 (2) | C8Z—C7Z—C21Z | 122 (3) |
C2D—C3D—H3D | 119.1 | C13Z—C8Z—C9Z | 119 (3) |
C4D—C3D—H3D | 119.1 | C13Z—C8Z—C7Z | 120 (3) |
C5D—C4D—C3D | 118 (2) | C9Z—C8Z—C7Z | 121 (3) |
C5D—C4D—C18D | 113 (2) | C10Z—C9Z—C8Z | 120 (3) |
C3D—C4D—C18D | 128 (2) | C10Z—C9Z—H9Z | 120.0 |
C6D—C5D—C4D | 120 (2) | C8Z—C9Z—H9Z | 120.0 |
C6D—C5D—H5D | 120.1 | C11Z—C10Z—C9Z | 121 (3) |
C4D—C5D—H5D | 120.1 | C11Z—C10Z—H10Z | 119.7 |
C5D—C6D—C1D | 120 (2) | C9Z—C10Z—H10Z | 119.7 |
C5D—C6D—C21D | 131 (2) | C10Z—C11Z—C12Z | 120 (3) |
C1D—C6D—C21D | 108.5 (18) | C10Z—C11Z—C14Z | 123 (3) |
O1D—C7D—C22D | 108 (2) | C12Z—C11Z—C14Z | 117 (3) |
O1D—C7D—C8D | 111 (2) | C13Z—C12Z—C11Z | 119 (3) |
C22D—C7D—C8D | 116.1 (18) | C13Z—C12Z—H12Z | 120.5 |
O1D—C7D—C1D | 110 (2) | C11Z—C12Z—H12Z | 120.5 |
C22D—C7D—C1D | 98.7 (17) | C8Z—C13Z—C12Z | 121 (3) |
C8D—C7D—C1D | 112 (2) | C8Z—C13Z—H13Z | 119.3 |
C13D—C8D—C9D | 117 (2) | C12Z—C13Z—H13Z | 119.3 |
C13D—C8D—C7D | 124 (2) | O3Z—C14Z—O2Z | 124.3 (7) |
C9D—C8D—C7D | 119 (2) | O3Z—C14Z—C11Z | 119.3 (17) |
C10D—C9D—C8D | 122 (2) | O2Z—C14Z—C11Z | 116.4 (17) |
C10D—C9D—H9D | 119.2 | C16Z—C15Z—C17Z | 118 (4) |
C8D—C9D—H9D | 119.2 | C16Z—C15Z—C2Z | 111 (3) |
C9D—C10D—C11D | 121 (2) | C17Z—C15Z—C2Z | 113 (3) |
C9D—C10D—H10D | 119.3 | C16Z—C15Z—H15Z | 104.5 |
C11D—C10D—H10D | 119.3 | C17Z—C15Z—H15Z | 104.5 |
C12D—C11D—C10D | 116 (2) | C2Z—C15Z—H15Z | 104.5 |
C12D—C11D—C14D | 124 (2) | C15Z—C16Z—H16J | 109.5 |
C10D—C11D—C14D | 120 (2) | C15Z—C16Z—H16K | 109.5 |
C13D—C12D—C11D | 122 (3) | H16J—C16Z—H16K | 109.5 |
C13D—C12D—H12D | 119.1 | C15Z—C16Z—H16L | 109.5 |
C11D—C12D—H12D | 119.1 | H16J—C16Z—H16L | 109.5 |
C8D—C13D—C12D | 122 (3) | H16K—C16Z—H16L | 109.5 |
C8D—C13D—H13D | 119.2 | C15Z—C17Z—H17J | 109.5 |
C12D—C13D—H13D | 119.2 | C15Z—C17Z—H17K | 109.5 |
O3D—C14D—O2D | 124.3 (7) | H17J—C17Z—H17K | 109.5 |
O3D—C14D—C11D | 114.8 (14) | C15Z—C17Z—H17L | 109.5 |
O2D—C14D—C11D | 120.5 (14) | H17J—C17Z—H17L | 109.5 |
C16D—C15D—C2D | 110 (3) | H17K—C17Z—H17L | 109.5 |
C16D—C15D—C17D | 114 (3) | C4Z—C18Z—C20Z | 118 (3) |
C2D—C15D—C17D | 111 (2) | C4Z—C18Z—C19Z | 98 (3) |
C16D—C15D—H15D | 107.1 | C20Z—C18Z—C19Z | 112 (4) |
C2D—C15D—H15D | 107.1 | C4Z—C18Z—H18Z | 109.4 |
C17D—C15D—H15D | 107.1 | C20Z—C18Z—H18Z | 109.4 |
C15D—C16D—H16D | 109.5 | C19Z—C18Z—H18Z | 109.4 |
C15D—C16D—H16E | 109.5 | C18Z—C19Z—H19J | 109.5 |
H16D—C16D—H16E | 109.5 | C18Z—C19Z—H19K | 109.5 |
C15D—C16D—H16F | 109.5 | H19J—C19Z—H19K | 109.5 |
H16D—C16D—H16F | 109.5 | C18Z—C19Z—H19L | 109.5 |
H16E—C16D—H16F | 109.5 | H19J—C19Z—H19L | 109.5 |
C15D—C17D—H17D | 109.5 | H19K—C19Z—H19L | 109.5 |
C15D—C17D—H17E | 109.5 | C18Z—C20Z—H20J | 109.5 |
H17D—C17D—H17E | 109.5 | C18Z—C20Z—H20K | 109.5 |
C15D—C17D—H17F | 109.5 | H20J—C20Z—H20K | 109.5 |
H17D—C17D—H17F | 109.5 | C18Z—C20Z—H20L | 109.5 |
H17E—C17D—H17F | 109.5 | H20J—C20Z—H20L | 109.5 |
C19D—C18D—C20D | 120 (3) | H20K—C20Z—H20L | 109.5 |
C19D—C18D—C4D | 123 (3) | C6Z—C21Z—C23Z | 120 (4) |
C20D—C18D—C4D | 116 (3) | C6Z—C21Z—C22Z | 109 (3) |
C19D—C18D—H18D | 93.6 | C23Z—C21Z—C22Z | 114 (3) |
C20D—C18D—H18D | 93.6 | C6Z—C21Z—C7Z | 86.2 (19) |
C4D—C18D—H18D | 93.6 | C23Z—C21Z—C7Z | 112 (3) |
C18D—C19D—H19D | 109.5 | C22Z—C21Z—C7Z | 114 (3) |
C18D—C19D—H19E | 109.5 | C21Z—C22Z—H22I | 109.5 |
H19D—C19D—H19E | 109.5 | C21Z—C22Z—H22J | 109.5 |
C18D—C19D—H19F | 109.5 | H22I—C22Z—H22J | 109.5 |
H19D—C19D—H19F | 109.5 | C21Z—C22Z—H22K | 109.5 |
H19E—C19D—H19F | 109.5 | H22I—C22Z—H22K | 109.5 |
C18D—C20D—H20D | 109.5 | H22J—C22Z—H22K | 109.5 |
C18D—C20D—H20E | 109.5 | C21Z—C23Z—H23J | 109.5 |
H20D—C20D—H20E | 109.5 | C21Z—C23Z—H23K | 109.5 |
C18D—C20D—H20F | 109.5 | H23J—C23Z—H23K | 109.5 |
H20D—C20D—H20F | 109.5 | C21Z—C23Z—H23L | 109.5 |
H20E—C20D—H20F | 109.5 | H23J—C23Z—H23L | 109.5 |
C23D—C21D—C6D | 118 (3) | H23K—C23Z—H23L | 109.5 |
C23D—C21D—C22D | 115 (3) | C25—N1—H1A | 109.5 |
C6D—C21D—C22D | 100.3 (19) | C25—N1—H1B | 109.5 |
C23D—C21D—H21D | 107.7 | H1A—N1—H1B | 109.5 |
C6D—C21D—H21D | 107.7 | C25—N1—H1C | 109.5 |
C22D—C21D—H21D | 107.7 | H1A—N1—H1C | 109.5 |
C7D—C22D—C21D | 109.0 (18) | H1B—N1—H1C | 109.5 |
C7D—C22D—H22D | 109.9 | C25—C24—H24A | 109.5 |
C21D—C22D—H22D | 109.9 | C25—C24—H24B | 109.5 |
C7D—C22D—H22E | 109.9 | H24A—C24—H24B | 109.5 |
C21D—C22D—H22E | 109.9 | C25—C24—H24C | 109.5 |
H22D—C22D—H22E | 108.3 | H24A—C24—H24C | 109.5 |
C21D—C23D—H23D | 109.5 | H24B—C24—H24C | 109.5 |
C21D—C23D—H23E | 109.5 | C26—C25—N1 | 109.5 (6) |
H23D—C23D—H23E | 109.5 | C26—C25—C24 | 114.1 (9) |
C21D—C23D—H23F | 109.5 | N1—C25—C24 | 108.0 (7) |
H23D—C23D—H23F | 109.5 | C26—C25—H25 | 108.4 |
H23E—C23D—H23F | 109.5 | N1—C25—H25 | 108.4 |
C6P—C1P—C2P | 120 (2) | C24—C25—H25 | 108.4 |
C6P—C1P—C7P | 144 (3) | C31—C26—C27 | 117.9 (11) |
C2P—C1P—C7P | 95.6 (19) | C31—C26—C25 | 123.1 (12) |
C3P—C2P—C1P | 120 (2) | C27—C26—C25 | 119.0 (12) |
C3P—C2P—C15P | 145 (3) | C26—C27—C28 | 121.2 (14) |
C1P—C2P—C15P | 93 (2) | C26—C27—H27 | 119.4 |
C4P—C3P—C2P | 118 (3) | C28—C27—H27 | 119.4 |
C4P—C3P—H3P | 121.1 | C29—C28—C27 | 118.5 (19) |
C2P—C3P—H3P | 121.1 | C29—C28—H28 | 120.7 |
C5P—C4P—C3P | 123 (3) | C27—C28—H28 | 120.7 |
C5P—C4P—C18P | 116 (3) | C28—C29—C30 | 123 (2) |
C3P—C4P—C18P | 121 (3) | C28—C29—H29 | 118.4 |
C4P—C5P—C6P | 119 (3) | C30—C29—H29 | 118.4 |
C4P—C5P—H5P | 120.6 | C29—C30—C31 | 117.8 (18) |
C6P—C5P—H5P | 120.6 | C29—C30—H30 | 121.1 |
C1P—C6P—C5P | 120 (3) | C31—C30—H30 | 121.1 |
C1P—C6P—C21P | 125 (3) | C26—C31—C30 | 121.3 (14) |
C5P—C6P—C21P | 115 (3) | C26—C31—H31 | 119.3 |
O1P—C7P—C1P | 119 (3) | C30—C31—H31 | 119.3 |
O1P—C7P—C8P | 105 (2) |
C31H39NO3 | Dx = 1.119 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 2131 reflections |
a = 6.3663 (6) Å | θ = 1.6–18.2° |
b = 13.5168 (12) Å | µ = 0.07 mm−1 |
c = 32.6694 (18) Å | T = 299 K |
V = 2811.3 (4) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.12 × 0.10 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 5436 independent reflections |
Radiation source: fine-focus sealed tube | 1956 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.128 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −16→14 |
Tmin = 0.856, Tmax = 1.000 | l = −40→40 |
24990 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.090 | H-atom parameters constrained |
wR(F2) = 0.211 | w = 1/[σ2(Fo2) + (0.0448P)2 + 0.5247P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
5436 reflections | Δρmax = 0.13 e Å−3 |
469 parameters | Δρmin = −0.15 e Å−3 |
554 restraints | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.6 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 1.044 (4) | 0.2420 (16) | 0.6339 (8) | 0.078 (7) | 0.381 (4) |
O2 | 0.6498 (10) | 0.6314 (4) | 0.51784 (16) | 0.0842 (18) | 0.381 (4) |
O3 | 0.3469 (11) | 0.6160 (5) | 0.54992 (16) | 0.094 (2) | 0.381 (4) |
C1 | 0.822 (6) | 0.279 (2) | 0.6917 (7) | 0.060 (10)* | 0.381 (4) |
C2 | 0.862 (5) | 0.346 (2) | 0.7232 (8) | 0.068 (9)* | 0.381 (4) |
C3 | 0.798 (5) | 0.326 (2) | 0.7633 (8) | 0.067 (8)* | 0.381 (4) |
H3 | 0.8305 | 0.3688 | 0.7845 | 0.080* | 0.381 (4) |
C4 | 0.683 (4) | 0.2390 (19) | 0.7711 (6) | 0.049 (7)* | 0.381 (4) |
C5 | 0.632 (5) | 0.1776 (18) | 0.7388 (6) | 0.059 (8)* | 0.381 (4) |
H5 | 0.5535 | 0.1208 | 0.7437 | 0.071* | 0.381 (4) |
C6 | 0.695 (5) | 0.1989 (19) | 0.6986 (7) | 0.057 (8)* | 0.381 (4) |
C7 | 0.913 (4) | 0.2956 (18) | 0.6493 (7) | 0.077 (8)* | 0.381 (4) |
C8 | 0.808 (4) | 0.3710 (14) | 0.6225 (6) | 0.053 (8)* | 0.381 (4) |
C9 | 0.924 (3) | 0.4099 (14) | 0.5912 (6) | 0.047 (6)* | 0.381 (4) |
H9 | 1.0621 | 0.3903 | 0.5869 | 0.056* | 0.381 (4) |
C10 | 0.829 (4) | 0.4793 (16) | 0.5661 (7) | 0.051 (7)* | 0.381 (4) |
H10 | 0.9071 | 0.5046 | 0.5444 | 0.061* | 0.381 (4) |
C11 | 0.631 (4) | 0.512 (2) | 0.5713 (8) | 0.058 (10)* | 0.381 (4) |
C12 | 0.509 (5) | 0.468 (2) | 0.6021 (8) | 0.060 (8)* | 0.381 (4) |
H12 | 0.3685 | 0.4841 | 0.6054 | 0.071* | 0.381 (4) |
C13 | 0.604 (5) | 0.398 (2) | 0.6277 (9) | 0.064 (9)* | 0.381 (4) |
H13 | 0.5262 | 0.3688 | 0.6486 | 0.077* | 0.381 (4) |
C14 | 0.5333 (16) | 0.5928 (6) | 0.5445 (2) | 0.072 (2) | 0.381 (4) |
C15 | 1.016 (5) | 0.4321 (18) | 0.7150 (11) | 0.076 (9)* | 0.381 (4) |
H15 | 1.0227 | 0.4410 | 0.6853 | 0.091* | 0.381 (4) |
C16 | 1.235 (5) | 0.407 (3) | 0.7292 (18) | 0.107 (18)* | 0.381 (4) |
H16A | 1.2786 | 0.3457 | 0.7168 | 0.161* | 0.381 (4) |
H16B | 1.3299 | 0.4586 | 0.7213 | 0.161* | 0.381 (4) |
H16C | 1.2359 | 0.3998 | 0.7584 | 0.161* | 0.381 (4) |
C17 | 0.932 (5) | 0.5274 (19) | 0.7328 (9) | 0.089 (8)* | 0.381 (4) |
H17A | 0.7927 | 0.5391 | 0.7226 | 0.134* | 0.381 (4) |
H17B | 0.9278 | 0.5224 | 0.7621 | 0.134* | 0.381 (4) |
H17C | 1.0217 | 0.5813 | 0.7250 | 0.134* | 0.381 (4) |
C18 | 0.623 (5) | 0.215 (3) | 0.8166 (7) | 0.082 (6)* | 0.381 (4) |
H18 | 0.6400 | 0.1438 | 0.8203 | 0.099* | 0.381 (4) |
C19 | 0.758 (5) | 0.265 (2) | 0.8485 (7) | 0.066 (8)* | 0.381 (4) |
H19A | 0.9027 | 0.2500 | 0.8434 | 0.099* | 0.381 (4) |
H19B | 0.7377 | 0.3356 | 0.8470 | 0.099* | 0.381 (4) |
H19C | 0.7188 | 0.2421 | 0.8752 | 0.099* | 0.381 (4) |
C20 | 0.397 (5) | 0.238 (3) | 0.8236 (13) | 0.103 (11)* | 0.381 (4) |
H20A | 0.3133 | 0.2054 | 0.8031 | 0.155* | 0.381 (4) |
H20B | 0.3559 | 0.2145 | 0.8502 | 0.155* | 0.381 (4) |
H20C | 0.3748 | 0.3080 | 0.8220 | 0.155* | 0.381 (4) |
C21 | 0.632 (4) | 0.1291 (18) | 0.6653 (8) | 0.079 (9)* | 0.381 (4) |
H21 | 0.6186 | 0.1661 | 0.6396 | 0.094* | 0.381 (4) |
C22 | 0.793 (4) | 0.0474 (19) | 0.6594 (9) | 0.093 (10)* | 0.381 (4) |
H22A | 0.7473 | 0.0042 | 0.6378 | 0.140* | 0.381 (4) |
H22B | 0.9259 | 0.0760 | 0.6523 | 0.140* | 0.381 (4) |
H22C | 0.8065 | 0.0105 | 0.6843 | 0.140* | 0.381 (4) |
C23 | 0.420 (4) | 0.076 (2) | 0.6746 (11) | 0.085 (9)* | 0.381 (4) |
H23A | 0.3863 | 0.0322 | 0.6524 | 0.128* | 0.381 (4) |
H23B | 0.4331 | 0.0389 | 0.6995 | 0.128* | 0.381 (4) |
H23C | 0.3112 | 0.1245 | 0.6775 | 0.128* | 0.381 (4) |
O1D | 1.092 (4) | 0.275 (3) | 0.6412 (10) | 0.068 (8) | 0.325 (4) |
O2D | 0.6498 (10) | 0.6314 (4) | 0.51784 (16) | 0.0842 (18) | 0.325 (4) |
O3D | 0.3469 (11) | 0.6160 (5) | 0.54992 (16) | 0.094 (2) | 0.325 (4) |
C1D | 0.802 (6) | 0.280 (3) | 0.6910 (7) | 0.061 (11)* | 0.325 (4) |
C2D | 0.899 (5) | 0.342 (2) | 0.7178 (8) | 0.060 (9)* | 0.325 (4) |
C3D | 0.850 (5) | 0.331 (2) | 0.7594 (8) | 0.069 (9)* | 0.325 (4) |
H3D | 0.9157 | 0.3721 | 0.7783 | 0.083* | 0.325 (4) |
C4D | 0.703 (5) | 0.260 (3) | 0.7738 (8) | 0.068 (10)* | 0.325 (4) |
C5D | 0.609 (7) | 0.198 (3) | 0.7441 (8) | 0.060 (10)* | 0.325 (4) |
H5D | 0.5097 | 0.1513 | 0.7521 | 0.072* | 0.325 (4) |
C6D | 0.664 (7) | 0.206 (3) | 0.7029 (8) | 0.060 (10)* | 0.325 (4) |
C7D | 0.862 (4) | 0.2736 (17) | 0.6446 (7) | 0.072 (9)* | 0.325 (4) |
C8D | 0.769 (4) | 0.3565 (18) | 0.6186 (7) | 0.053 (8)* | 0.325 (4) |
C9D | 0.872 (5) | 0.385 (2) | 0.5827 (8) | 0.060 (8)* | 0.325 (4) |
H9D | 0.9945 | 0.3536 | 0.5746 | 0.072* | 0.325 (4) |
C10D | 0.791 (5) | 0.461 (2) | 0.5596 (9) | 0.061 (9)* | 0.325 (4) |
H10D | 0.8611 | 0.4794 | 0.5359 | 0.073* | 0.325 (4) |
C11D | 0.610 (4) | 0.5107 (19) | 0.5702 (9) | 0.057 (11)* | 0.325 (4) |
C12D | 0.506 (6) | 0.483 (3) | 0.6059 (10) | 0.069 (11)* | 0.325 (4) |
H12D | 0.3835 | 0.5143 | 0.6140 | 0.082* | 0.325 (4) |
C13D | 0.590 (5) | 0.406 (3) | 0.6290 (11) | 0.064 (11)* | 0.325 (4) |
H13D | 0.5204 | 0.3873 | 0.6528 | 0.077* | 0.325 (4) |
C14D | 0.5333 (16) | 0.5928 (6) | 0.5445 (2) | 0.072 (2) | 0.325 (4) |
C15D | 1.041 (4) | 0.426 (2) | 0.7049 (11) | 0.075 (10)* | 0.325 (4) |
H15D | 1.0737 | 0.4141 | 0.6760 | 0.091* | 0.325 (4) |
C16D | 1.245 (5) | 0.424 (4) | 0.7266 (17) | 0.059 (12)* | 0.325 (4) |
H16D | 1.3298 | 0.4782 | 0.7175 | 0.089* | 0.325 (4) |
H16E | 1.2208 | 0.4295 | 0.7556 | 0.089* | 0.325 (4) |
H16F | 1.3154 | 0.3627 | 0.7209 | 0.089* | 0.325 (4) |
C17D | 0.931 (6) | 0.526 (2) | 0.7068 (12) | 0.085 (10)* | 0.325 (4) |
H17D | 0.8003 | 0.5225 | 0.6922 | 0.128* | 0.325 (4) |
H17E | 0.9043 | 0.5432 | 0.7348 | 0.128* | 0.325 (4) |
H17F | 1.0189 | 0.5755 | 0.6945 | 0.128* | 0.325 (4) |
C18D | 0.640 (5) | 0.232 (3) | 0.8183 (8) | 0.085 (7)* | 0.325 (4) |
H18D | 0.6137 | 0.1615 | 0.8133 | 0.102* | 0.325 (4) |
C19D | 0.805 (5) | 0.219 (3) | 0.8498 (8) | 0.091 (9)* | 0.325 (4) |
H19D | 0.9355 | 0.2022 | 0.8367 | 0.137* | 0.325 (4) |
H19E | 0.8222 | 0.2795 | 0.8648 | 0.137* | 0.325 (4) |
H19F | 0.7656 | 0.1669 | 0.8682 | 0.137* | 0.325 (4) |
C20D | 0.422 (5) | 0.258 (4) | 0.8305 (13) | 0.094 (11)* | 0.325 (4) |
H20D | 0.3354 | 0.2638 | 0.8065 | 0.141* | 0.325 (4) |
H20E | 0.3660 | 0.2080 | 0.8481 | 0.141* | 0.325 (4) |
H20F | 0.4226 | 0.3205 | 0.8447 | 0.141* | 0.325 (4) |
C21D | 0.602 (6) | 0.148 (2) | 0.6648 (10) | 0.083 (11)* | 0.325 (4) |
H21D | 0.4789 | 0.1824 | 0.6535 | 0.099* | 0.325 (4) |
C22D | 0.785 (4) | 0.1705 (16) | 0.6352 (7) | 0.089 (9)* | 0.325 (4) |
H22D | 0.8968 | 0.1229 | 0.6390 | 0.107* | 0.325 (4) |
H22E | 0.7365 | 0.1666 | 0.6071 | 0.107* | 0.325 (4) |
C23D | 0.539 (6) | 0.0440 (19) | 0.6696 (9) | 0.104 (11)* | 0.325 (4) |
H23D | 0.5041 | 0.0169 | 0.6433 | 0.157* | 0.325 (4) |
H23E | 0.6530 | 0.0071 | 0.6813 | 0.157* | 0.325 (4) |
H23F | 0.4188 | 0.0400 | 0.6873 | 0.157* | 0.325 (4) |
O1P | 1.123 (6) | 0.308 (3) | 0.6532 (14) | 0.075 (10)* | 0.162 (4) |
O2P | 0.6498 (10) | 0.6314 (4) | 0.51784 (16) | 0.0842 (18) | 0.162 (4) |
O3P | 0.3469 (11) | 0.6160 (5) | 0.54992 (16) | 0.094 (2) | 0.162 (4) |
C1P | 0.806 (7) | 0.294 (3) | 0.7011 (10) | 0.059 (12)* | 0.162 (4) |
C2P | 0.875 (7) | 0.346 (3) | 0.7361 (10) | 0.057 (12)* | 0.162 (4) |
C3P | 0.793 (8) | 0.323 (4) | 0.7747 (11) | 0.066 (13)* | 0.162 (4) |
H3P | 0.8362 | 0.3573 | 0.7979 | 0.080* | 0.162 (4) |
C4P | 0.646 (8) | 0.248 (4) | 0.7777 (11) | 0.075 (14)* | 0.162 (4) |
C5P | 0.574 (10) | 0.198 (5) | 0.7436 (11) | 0.062 (13)* | 0.162 (4) |
H5P | 0.4700 | 0.1497 | 0.7464 | 0.074* | 0.162 (4) |
C6P | 0.656 (10) | 0.219 (4) | 0.7052 (12) | 0.058 (13)* | 0.162 (4) |
C7P | 0.941 (5) | 0.3505 (19) | 0.6710 (8) | 0.053 (10)* | 0.162 (4) |
C8P | 0.839 (5) | 0.4131 (16) | 0.6378 (7) | 0.049 (10)* | 0.162 (4) |
C9P | 0.954 (5) | 0.458 (2) | 0.6074 (9) | 0.071 (11)* | 0.162 (4) |
H9P | 1.0989 | 0.4487 | 0.6072 | 0.086* | 0.162 (4) |
C10P | 0.863 (5) | 0.516 (2) | 0.5768 (10) | 0.065 (12)* | 0.162 (4) |
H10P | 0.9473 | 0.5445 | 0.5568 | 0.078* | 0.162 (4) |
C11P | 0.649 (5) | 0.5312 (11) | 0.5761 (7) | 0.067 (14)* | 0.162 (4) |
C12P | 0.526 (7) | 0.487 (3) | 0.6068 (10) | 0.066 (14)* | 0.162 (4) |
H12P | 0.3811 | 0.4961 | 0.6071 | 0.079* | 0.162 (4) |
C13P | 0.624 (6) | 0.430 (3) | 0.6363 (11) | 0.052 (12)* | 0.162 (4) |
H13P | 0.5401 | 0.4016 | 0.6565 | 0.062* | 0.162 (4) |
C14P | 0.5333 (16) | 0.5928 (6) | 0.5445 (2) | 0.072 (2) | 0.162 (4) |
C15P | 0.992 (7) | 0.422 (3) | 0.7111 (11) | 0.076 (14)* | 0.162 (4) |
C16P | 1.228 (7) | 0.434 (5) | 0.7136 (18) | 0.090 (18)* | 0.162 (4) |
H16G | 1.2712 | 0.4859 | 0.6953 | 0.135* | 0.162 (4) |
H16H | 1.2671 | 0.4509 | 0.7411 | 0.135* | 0.162 (4) |
H16I | 1.2954 | 0.3733 | 0.7058 | 0.135* | 0.162 (4) |
C17P | 0.895 (12) | 0.524 (3) | 0.715 (2) | 0.073 (13)* | 0.162 (4) |
H17G | 0.9733 | 0.5697 | 0.6984 | 0.110* | 0.162 (4) |
H17H | 0.7521 | 0.5214 | 0.7051 | 0.110* | 0.162 (4) |
H17I | 0.8965 | 0.5443 | 0.7428 | 0.110* | 0.162 (4) |
C18P | 0.549 (7) | 0.213 (4) | 0.8177 (11) | 0.082 (8)* | 0.162 (4) |
H18P | 0.5319 | 0.1411 | 0.8168 | 0.098* | 0.162 (4) |
C19P | 0.686 (9) | 0.240 (6) | 0.8531 (14) | 0.089 (14)* | 0.162 (4) |
H19G | 0.6231 | 0.2175 | 0.8781 | 0.134* | 0.162 (4) |
H19H | 0.8214 | 0.2093 | 0.8499 | 0.134* | 0.162 (4) |
H19I | 0.7034 | 0.3106 | 0.8541 | 0.134* | 0.162 (4) |
C20P | 0.333 (7) | 0.262 (5) | 0.8157 (18) | 0.070 (13)* | 0.162 (4) |
H20G | 0.2598 | 0.2389 | 0.7919 | 0.106* | 0.162 (4) |
H20H | 0.2543 | 0.2448 | 0.8398 | 0.106* | 0.162 (4) |
H20I | 0.3494 | 0.3323 | 0.8143 | 0.106* | 0.162 (4) |
C21P | 0.573 (8) | 0.154 (4) | 0.6712 (15) | 0.078 (14)* | 0.162 (4) |
H21P | 0.5364 | 0.1977 | 0.6483 | 0.093* | 0.162 (4) |
C22P | 0.749 (9) | 0.086 (4) | 0.6564 (18) | 0.076 (16)* | 0.162 (4) |
H22F | 0.6970 | 0.0443 | 0.6348 | 0.115* | 0.162 (4) |
H22G | 0.8643 | 0.1247 | 0.6464 | 0.115* | 0.162 (4) |
H22H | 0.7960 | 0.0452 | 0.6787 | 0.115* | 0.162 (4) |
C23P | 0.380 (9) | 0.093 (6) | 0.681 (3) | 0.12 (3)* | 0.162 (4) |
H23G | 0.3398 | 0.0545 | 0.6579 | 0.185* | 0.162 (4) |
H23H | 0.4105 | 0.0495 | 0.7038 | 0.185* | 0.162 (4) |
H23I | 0.2662 | 0.1362 | 0.6888 | 0.185* | 0.162 (4) |
O1Z | 1.112 (7) | 0.278 (6) | 0.651 (2) | 0.069 (11)* | 0.132 (4) |
O2Z | 0.6498 (10) | 0.6314 (4) | 0.51784 (16) | 0.0842 (18) | 0.132 (4) |
O3Z | 0.3469 (11) | 0.6160 (5) | 0.54992 (16) | 0.094 (2) | 0.132 (4) |
C6Z | 0.753 (7) | 0.220 (2) | 0.7065 (9) | 0.050 (12)* | 0.132 (4) |
C1Z | 0.875 (6) | 0.303 (2) | 0.6988 (8) | 0.055 (13)* | 0.132 (4) |
C2Z | 0.907 (7) | 0.372 (2) | 0.7296 (10) | 0.067 (14)* | 0.132 (4) |
C3Z | 0.819 (7) | 0.358 (3) | 0.7681 (9) | 0.077 (14)* | 0.132 (4) |
H3Z | 0.8422 | 0.4052 | 0.7892 | 0.092* | 0.132 (4) |
C4Z | 0.698 (6) | 0.275 (3) | 0.7758 (8) | 0.066 (14)* | 0.132 (4) |
C5Z | 0.665 (7) | 0.205 (3) | 0.7450 (10) | 0.059 (14)* | 0.132 (4) |
H5Z | 0.5814 | 0.1484 | 0.7502 | 0.071* | 0.132 (4) |
C7Z | 0.889 (7) | 0.287 (2) | 0.6529 (10) | 0.076 (15)* | 0.132 (4) |
C8Z | 0.801 (8) | 0.367 (3) | 0.6240 (12) | 0.053 (15)* | 0.132 (4) |
C9Z | 0.888 (10) | 0.383 (5) | 0.5855 (16) | 0.063 (14)* | 0.132 (4) |
H9Z | 1.0044 | 0.3446 | 0.5767 | 0.075* | 0.132 (4) |
C10Z | 0.804 (9) | 0.454 (4) | 0.5597 (13) | 0.066 (14)* | 0.132 (4) |
H10Z | 0.8637 | 0.4654 | 0.5334 | 0.079* | 0.132 (4) |
C11Z | 0.634 (5) | 0.5107 (15) | 0.5725 (10) | 0.059 (15)* | 0.132 (4) |
C12Z | 0.546 (7) | 0.496 (3) | 0.6109 (12) | 0.064 (14)* | 0.132 (4) |
H12Z | 0.4296 | 0.5339 | 0.6197 | 0.077* | 0.132 (4) |
C13Z | 0.630 (8) | 0.423 (4) | 0.6367 (11) | 0.057 (13)* | 0.132 (4) |
H13Z | 0.5703 | 0.4130 | 0.6630 | 0.069* | 0.132 (4) |
C14Z | 0.5333 (16) | 0.5928 (6) | 0.5445 (2) | 0.072 (2) | 0.132 (4) |
C15Z | 1.032 (8) | 0.462 (3) | 0.7198 (19) | 0.075 (14)* | 0.132 (4) |
H15Z | 1.0605 | 0.4559 | 0.6904 | 0.090* | 0.132 (4) |
C16Z | 1.239 (7) | 0.452 (5) | 0.739 (2) | 0.11 (3)* | 0.132 (4) |
H16J | 1.2946 | 0.3870 | 0.7338 | 0.162* | 0.132 (4) |
H16K | 1.3329 | 0.5008 | 0.7283 | 0.162* | 0.132 (4) |
H16L | 1.2259 | 0.4609 | 0.7683 | 0.162* | 0.132 (4) |
C17Z | 0.912 (11) | 0.555 (3) | 0.723 (3) | 0.083 (15)* | 0.132 (4) |
H17J | 0.7811 | 0.5484 | 0.7091 | 0.124* | 0.132 (4) |
H17K | 0.8848 | 0.5681 | 0.7519 | 0.124* | 0.132 (4) |
H17L | 0.9919 | 0.6080 | 0.7119 | 0.124* | 0.132 (4) |
C18Z | 0.611 (8) | 0.266 (4) | 0.8183 (11) | 0.080 (9)* | 0.132 (4) |
H18Z | 0.6005 | 0.1959 | 0.8252 | 0.096* | 0.132 (4) |
C19Z | 0.789 (9) | 0.311 (6) | 0.8431 (17) | 0.097 (14)* | 0.132 (4) |
H19J | 0.7525 | 0.3098 | 0.8716 | 0.145* | 0.132 (4) |
H19K | 0.9145 | 0.2725 | 0.8390 | 0.145* | 0.132 (4) |
H19L | 0.8129 | 0.3776 | 0.8345 | 0.145* | 0.132 (4) |
C20Z | 0.403 (9) | 0.315 (6) | 0.829 (2) | 0.102 (15)* | 0.132 (4) |
H20J | 0.3698 | 0.3027 | 0.8570 | 0.153* | 0.132 (4) |
H20K | 0.4132 | 0.3850 | 0.8242 | 0.153* | 0.132 (4) |
H20L | 0.2942 | 0.2881 | 0.8117 | 0.153* | 0.132 (4) |
C21Z | 0.762 (7) | 0.184 (2) | 0.6626 (10) | 0.079 (13)* | 0.132 (4) |
C22Z | 0.898 (9) | 0.091 (3) | 0.6614 (17) | 0.078 (17)* | 0.132 (4) |
H22I | 0.9057 | 0.0670 | 0.6338 | 0.118* | 0.132 (4) |
H22J | 1.0364 | 0.1067 | 0.6710 | 0.118* | 0.132 (4) |
H22K | 0.8371 | 0.0412 | 0.6787 | 0.118* | 0.132 (4) |
C23Z | 0.560 (8) | 0.172 (5) | 0.6381 (19) | 0.12 (2)* | 0.132 (4) |
H23J | 0.5935 | 0.1489 | 0.6111 | 0.183* | 0.132 (4) |
H23K | 0.4699 | 0.1254 | 0.6514 | 0.183* | 0.132 (4) |
H23L | 0.4905 | 0.2350 | 0.6362 | 0.183* | 0.132 (4) |
N1 | 0.0572 (10) | 0.6672 (4) | 0.49239 (16) | 0.0679 (19) | |
H1A | 0.1557 | 0.6438 | 0.5091 | 0.082* | |
H1B | −0.0692 | 0.6524 | 0.5023 | 0.082* | |
H1C | 0.0700 | 0.7326 | 0.4904 | 0.082* | |
C24 | 0.2954 (16) | 0.6520 (7) | 0.4331 (2) | 0.104 (3) | |
H24A | 0.4041 | 0.6353 | 0.4523 | 0.157* | |
H24B | 0.2961 | 0.7221 | 0.4285 | 0.157* | |
H24C | 0.3197 | 0.6181 | 0.4078 | 0.157* | |
C25 | 0.0826 (14) | 0.6211 (6) | 0.4505 (2) | 0.074 (2) | |
H25 | −0.0267 | 0.6485 | 0.4327 | 0.089* | |
C26 | 0.048 (2) | 0.5121 (8) | 0.4534 (3) | 0.081 (3) | |
C27 | −0.136 (2) | 0.4713 (10) | 0.4398 (3) | 0.109 (3) | |
H27 | −0.2409 | 0.5123 | 0.4295 | 0.131* | |
C28 | −0.169 (3) | 0.3692 (13) | 0.4410 (4) | 0.150 (6) | |
H28 | −0.2960 | 0.3422 | 0.4327 | 0.180* | |
C29 | −0.011 (4) | 0.3101 (14) | 0.4544 (6) | 0.183 (10) | |
H29 | −0.0274 | 0.2418 | 0.4534 | 0.219* | |
C30 | 0.171 (4) | 0.3487 (13) | 0.4693 (5) | 0.181 (7) | |
H30 | 0.2740 | 0.3074 | 0.4800 | 0.218* | |
C31 | 0.202 (2) | 0.4503 (10) | 0.4683 (3) | 0.127 (4) | |
H31 | 0.3274 | 0.4769 | 0.4777 | 0.153* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.092 (12) | 0.067 (13) | 0.074 (11) | 0.026 (10) | 0.024 (10) | 0.007 (10) |
O2 | 0.081 (4) | 0.098 (4) | 0.074 (3) | −0.004 (4) | 0.013 (3) | 0.033 (3) |
O3 | 0.080 (4) | 0.134 (5) | 0.067 (4) | 0.023 (4) | −0.006 (4) | 0.037 (4) |
C14 | 0.085 (6) | 0.071 (5) | 0.058 (5) | 0.003 (5) | −0.015 (5) | −0.001 (4) |
O1D | 0.073 (12) | 0.062 (14) | 0.068 (14) | −0.002 (12) | 0.006 (11) | −0.011 (12) |
O2D | 0.081 (4) | 0.098 (4) | 0.074 (3) | −0.004 (4) | 0.013 (3) | 0.033 (3) |
O3D | 0.080 (4) | 0.134 (5) | 0.067 (4) | 0.023 (4) | −0.006 (4) | 0.037 (4) |
C14D | 0.085 (6) | 0.071 (5) | 0.058 (5) | 0.003 (5) | −0.015 (5) | −0.001 (4) |
O2P | 0.081 (4) | 0.098 (4) | 0.074 (3) | −0.004 (4) | 0.013 (3) | 0.033 (3) |
O3P | 0.080 (4) | 0.134 (5) | 0.067 (4) | 0.023 (4) | −0.006 (4) | 0.037 (4) |
C14P | 0.085 (6) | 0.071 (5) | 0.058 (5) | 0.003 (5) | −0.015 (5) | −0.001 (4) |
O2Z | 0.081 (4) | 0.098 (4) | 0.074 (3) | −0.004 (4) | 0.013 (3) | 0.033 (3) |
O3Z | 0.080 (4) | 0.134 (5) | 0.067 (4) | 0.023 (4) | −0.006 (4) | 0.037 (4) |
C14Z | 0.085 (6) | 0.071 (5) | 0.058 (5) | 0.003 (5) | −0.015 (5) | −0.001 (4) |
N1 | 0.073 (5) | 0.085 (4) | 0.045 (4) | 0.004 (4) | −0.002 (4) | 0.014 (3) |
C24 | 0.114 (9) | 0.138 (8) | 0.062 (5) | −0.004 (7) | 0.029 (6) | 0.002 (6) |
C25 | 0.078 (7) | 0.094 (7) | 0.050 (5) | 0.001 (6) | −0.011 (5) | 0.011 (5) |
C26 | 0.102 (9) | 0.093 (8) | 0.047 (5) | −0.004 (8) | −0.003 (6) | −0.004 (5) |
C27 | 0.114 (11) | 0.126 (11) | 0.089 (8) | −0.004 (9) | 0.015 (7) | −0.023 (7) |
C28 | 0.168 (17) | 0.133 (14) | 0.150 (13) | −0.046 (12) | 0.031 (12) | −0.039 (11) |
C29 | 0.30 (3) | 0.103 (13) | 0.149 (15) | −0.019 (16) | 0.033 (18) | −0.025 (11) |
C30 | 0.28 (2) | 0.113 (15) | 0.154 (14) | 0.029 (14) | −0.028 (15) | 0.002 (10) |
C31 | 0.172 (14) | 0.101 (10) | 0.109 (9) | 0.008 (10) | −0.025 (9) | −0.003 (7) |
O1—C7 | 1.22 (2) | C4P—C18P | 1.52 (2) |
O2—C14 | 1.258 (9) | C5P—C6P | 1.39 (2) |
O3—C14 | 1.240 (9) | C5P—H5P | 0.9300 |
C1—C6 | 1.373 (19) | C6P—C21P | 1.51 (2) |
C1—C2 | 1.40 (2) | C7P—C8P | 1.52 (2) |
C1—C7 | 1.515 (19) | C7P—C15P | 1.66 (2) |
C2—C3 | 1.40 (2) | C8P—C9P | 1.37 (2) |
C2—C15 | 1.54 (2) | C8P—C13P | 1.39 (2) |
C3—C4 | 1.40 (2) | C9P—C10P | 1.40 (2) |
C3—H3 | 0.9300 | C9P—H9P | 0.9300 |
C4—C5 | 1.38 (2) | C10P—C11P | 1.38 (2) |
C4—C18 | 1.57 (2) | C10P—H10P | 0.9300 |
C5—C6 | 1.402 (19) | C11P—C12P | 1.40 (2) |
C5—H5 | 0.9300 | C11P—C14P | 1.52 (2) |
C6—C21 | 1.50 (2) | C12P—C13P | 1.38 (2) |
C7—C8 | 1.500 (19) | C12P—H12P | 0.9300 |
C8—C13 | 1.36 (2) | C13P—H13P | 0.9300 |
C8—C9 | 1.365 (18) | C15P—C16P | 1.51 (3) |
C9—C10 | 1.384 (18) | C15P—C17P | 1.52 (2) |
C9—H9 | 0.9300 | C16P—H16G | 0.9600 |
C10—C11 | 1.35 (2) | C16P—H16H | 0.9600 |
C10—H10 | 0.9300 | C16P—H16I | 0.9600 |
C11—C12 | 1.41 (2) | C17P—H17G | 0.9600 |
C11—C14 | 1.527 (18) | C17P—H17H | 0.9600 |
C12—C13 | 1.40 (2) | C17P—H17I | 0.9600 |
C12—H12 | 0.9300 | C18P—C19P | 1.50 (3) |
C13—H13 | 0.9300 | C18P—C20P | 1.52 (3) |
C15—C16 | 1.51 (2) | C18P—H18P | 0.9800 |
C15—C17 | 1.51 (2) | C19P—H19G | 0.9600 |
C15—H15 | 0.9800 | C19P—H19H | 0.9600 |
C16—H16A | 0.9600 | C19P—H19I | 0.9600 |
C16—H16B | 0.9600 | C20P—H20G | 0.9600 |
C16—H16C | 0.9600 | C20P—H20H | 0.9600 |
C17—H17A | 0.9600 | C20P—H20I | 0.9600 |
C17—H17B | 0.9600 | C21P—C23P | 1.52 (3) |
C17—H17C | 0.9600 | C21P—C22P | 1.53 (3) |
C18—C20 | 1.49 (2) | C21P—H21P | 0.9800 |
C18—C19 | 1.51 (2) | C22P—H22F | 0.9600 |
C18—H18 | 0.9800 | C22P—H22G | 0.9600 |
C19—H19A | 0.9600 | C22P—H22H | 0.9600 |
C19—H19B | 0.9600 | C23P—H23G | 0.9600 |
C19—H19C | 0.9600 | C23P—H23H | 0.9600 |
C20—H20A | 0.9600 | C23P—H23I | 0.9600 |
C20—H20B | 0.9600 | O1Z—C7Z | 1.42 (3) |
C20—H20C | 0.9600 | O2Z—C14Z | 1.258 (9) |
C21—C22 | 1.52 (2) | O3Z—C14Z | 1.240 (9) |
C21—C23 | 1.56 (2) | C6Z—C5Z | 1.3894 |
C21—H21 | 0.9800 | C6Z—C1Z | 1.3922 |
C22—H22A | 0.9600 | C6Z—C21Z | 1.51 (2) |
C22—H22B | 0.9600 | C1Z—C2Z | 1.3890 |
C22—H22C | 0.9600 | C1Z—C7Z | 1.52 (2) |
C23—H23A | 0.9600 | C2Z—C3Z | 1.3895 |
C23—H23B | 0.9600 | C2Z—C15Z | 1.48 (2) |
C23—H23C | 0.9600 | C3Z—C4Z | 1.3886 |
O1D—C7D | 1.47 (2) | C3Z—H3Z | 0.9503 |
O2D—C14D | 1.258 (9) | C4Z—C5Z | 1.3900 |
O3D—C14D | 1.240 (9) | C4Z—C18Z | 1.50 (2) |
C1D—C2D | 1.36 (2) | C5Z—H5Z | 0.9508 |
C1D—C6D | 1.38 (2) | C7Z—C8Z | 1.55 (2) |
C1D—C7D | 1.57 (2) | C7Z—C21Z | 1.65 (2) |
C2D—C3D | 1.40 (2) | C8Z—C13Z | 1.3906 |
C2D—C15D | 1.51 (2) | C8Z—C9Z | 1.3919 |
C3D—C4D | 1.42 (2) | C9Z—C10Z | 1.3876 |
C3D—H3D | 0.9300 | C9Z—H9Z | 0.9485 |
C4D—C5D | 1.41 (2) | C10Z—C11Z | 1.3920 |
C4D—C18D | 1.56 (2) | C10Z—H10Z | 0.9501 |
C5D—C6D | 1.39 (2) | C11Z—C12Z | 1.3870 |
C5D—H5D | 0.9300 | C11Z—C14Z | 1.573 (19) |
C6D—C21D | 1.52 (2) | C12Z—C13Z | 1.3947 |
C7D—C22D | 1.51 (2) | C12Z—H12Z | 0.9481 |
C7D—C8D | 1.52 (2) | C13Z—H13Z | 0.9480 |
C8D—C13D | 1.36 (2) | C15Z—C16Z | 1.47 (3) |
C8D—C9D | 1.40 (2) | C15Z—C17Z | 1.47 (3) |
C9D—C10D | 1.37 (2) | C15Z—H15Z | 0.9800 |
C9D—H9D | 0.9300 | C16Z—H16J | 0.9600 |
C10D—C11D | 1.38 (2) | C16Z—H16K | 0.9600 |
C10D—H10D | 0.9300 | C16Z—H16L | 0.9600 |
C11D—C12D | 1.39 (2) | C17Z—H17J | 0.9600 |
C11D—C14D | 1.475 (18) | C17Z—H17K | 0.9600 |
C12D—C13D | 1.39 (2) | C17Z—H17L | 0.9600 |
C12D—H12D | 0.9300 | C18Z—C20Z | 1.52 (3) |
C13D—H13D | 0.9300 | C18Z—C19Z | 1.52 (3) |
C15D—C16D | 1.48 (2) | C18Z—H18Z | 0.9800 |
C15D—C17D | 1.53 (2) | C19Z—H19J | 0.9600 |
C15D—H15D | 0.9800 | C19Z—H19K | 0.9600 |
C16D—H16D | 0.9600 | C19Z—H19L | 0.9600 |
C16D—H16E | 0.9600 | C20Z—H20J | 0.9600 |
C16D—H16F | 0.9600 | C20Z—H20K | 0.9600 |
C17D—H17D | 0.9600 | C20Z—H20L | 0.9600 |
C17D—H17E | 0.9600 | C21Z—C23Z | 1.52 (2) |
C17D—H17F | 0.9600 | C21Z—C22Z | 1.52 (2) |
C18D—C19D | 1.48 (2) | C22Z—H22I | 0.9600 |
C18D—C20D | 1.49 (2) | C22Z—H22J | 0.9600 |
C18D—H18D | 0.9800 | C22Z—H22K | 0.9600 |
C19D—H19D | 0.9600 | C23Z—H23J | 0.9600 |
C19D—H19E | 0.9600 | C23Z—H23K | 0.9600 |
C19D—H19F | 0.9600 | C23Z—H23L | 0.9600 |
C20D—H20D | 0.9600 | N1—C25 | 1.513 (9) |
C20D—H20E | 0.9600 | N1—H1A | 0.8900 |
C20D—H20F | 0.9600 | N1—H1B | 0.8900 |
C21D—C23D | 1.47 (2) | N1—H1C | 0.8900 |
C21D—C22D | 1.54 (2) | C24—C25 | 1.527 (11) |
C21D—H21D | 0.9800 | C24—H24A | 0.9600 |
C22D—H22D | 0.9700 | C24—H24B | 0.9600 |
C22D—H22E | 0.9700 | C24—H24C | 0.9600 |
C23D—H23D | 0.9600 | C25—C26 | 1.493 (12) |
C23D—H23E | 0.9600 | C25—H25 | 0.9800 |
C23D—H23F | 0.9600 | C26—C27 | 1.369 (14) |
O1P—C7P | 1.42 (2) | C26—C31 | 1.375 (14) |
O2P—C14P | 1.258 (9) | C27—C28 | 1.396 (15) |
O3P—C14P | 1.240 (9) | C27—H27 | 0.9300 |
C1P—C6P | 1.40 (2) | C28—C29 | 1.36 (2) |
C1P—C2P | 1.41 (2) | C28—H28 | 0.9300 |
C1P—C7P | 1.51 (2) | C29—C30 | 1.36 (2) |
C2P—C3P | 1.40 (2) | C29—H29 | 0.9300 |
C2P—C15P | 1.51 (2) | C30—C31 | 1.387 (17) |
C3P—C4P | 1.38 (2) | C30—H30 | 0.9300 |
C3P—H3P | 0.9300 | C31—H31 | 0.9300 |
C4P—C5P | 1.38 (2) | ||
C6—C1—C2 | 119.9 (18) | C1P—C7P—C8P | 120 (2) |
C6—C1—C7 | 119.3 (19) | O1P—C7P—C15P | 113 (3) |
C2—C1—C7 | 120.8 (19) | C1P—C7P—C15P | 83.6 (17) |
C1—C2—C3 | 120.6 (19) | C8P—C7P—C15P | 109.0 (17) |
C1—C2—C15 | 118 (2) | C9P—C8P—C13P | 115 (2) |
C3—C2—C15 | 120 (2) | C9P—C8P—C7P | 122 (2) |
C2—C3—C4 | 119 (2) | C13P—C8P—C7P | 123 (2) |
C2—C3—H3 | 120.3 | C8P—C9P—C10P | 123 (3) |
C4—C3—H3 | 120.3 | C8P—C9P—H9P | 118.6 |
C5—C4—C3 | 118.8 (18) | C10P—C9P—H9P | 118.6 |
C5—C4—C18 | 123.1 (19) | C11P—C10P—C9P | 120 (3) |
C3—C4—C18 | 118.1 (19) | C11P—C10P—H10P | 119.8 |
C4—C5—C6 | 121.7 (19) | C9P—C10P—H10P | 119.8 |
C4—C5—H5 | 119.2 | C10P—C11P—C12P | 119 (2) |
C6—C5—H5 | 119.2 | C10P—C11P—C14P | 125 (2) |
C1—C6—C5 | 119.1 (18) | C12P—C11P—C14P | 117 (2) |
C1—C6—C21 | 122.5 (18) | C13P—C12P—C11P | 119 (3) |
C5—C6—C21 | 118.3 (18) | C13P—C12P—H12P | 120.6 |
O1—C7—C8 | 117.9 (19) | C11P—C12P—H12P | 120.6 |
O1—C7—C1 | 124 (2) | C12P—C13P—C8P | 124 (3) |
C8—C7—C1 | 118 (2) | C12P—C13P—H13P | 118.0 |
C13—C8—C9 | 120.4 (18) | C8P—C13P—H13P | 118.0 |
C13—C8—C7 | 122.1 (19) | O3P—C14P—O2P | 123.9 (7) |
C9—C8—C7 | 117.4 (18) | O3P—C14P—C11P | 120.5 (16) |
C8—C9—C10 | 118.1 (18) | O2P—C14P—C11P | 114.4 (16) |
C8—C9—H9 | 120.9 | C2P—C15P—C16P | 123 (3) |
C10—C9—H9 | 120.9 | C2P—C15P—C17P | 112 (3) |
C11—C10—C9 | 123.7 (19) | C16P—C15P—C17P | 107 (3) |
C11—C10—H10 | 118.1 | C2P—C15P—C7P | 86.3 (18) |
C9—C10—H10 | 118.1 | C16P—C15P—C7P | 108 (3) |
C10—C11—C12 | 117.6 (17) | C17P—C15P—C7P | 120 (3) |
C10—C11—C14 | 122.9 (18) | C15P—C16P—H16G | 109.5 |
C12—C11—C14 | 119.5 (18) | C15P—C16P—H16H | 109.5 |
C13—C12—C11 | 119 (2) | H16G—C16P—H16H | 109.5 |
C13—C12—H12 | 120.7 | C15P—C16P—H16I | 109.5 |
C11—C12—H12 | 120.7 | H16G—C16P—H16I | 109.5 |
C8—C13—C12 | 121 (2) | H16H—C16P—H16I | 109.5 |
C8—C13—H13 | 119.4 | C15P—C17P—H17G | 109.5 |
C12—C13—H13 | 119.4 | C15P—C17P—H17H | 109.5 |
O3—C14—O2 | 123.9 (7) | H17G—C17P—H17H | 109.5 |
O3—C14—C11 | 119.2 (13) | C15P—C17P—H17I | 109.5 |
O2—C14—C11 | 116.9 (13) | H17G—C17P—H17I | 109.5 |
C16—C15—C17 | 114 (3) | H17H—C17P—H17I | 109.5 |
C16—C15—C2 | 111 (2) | C19P—C18P—C4P | 110 (3) |
C17—C15—C2 | 110 (2) | C19P—C18P—C20P | 117 (4) |
C16—C15—H15 | 107.0 | C4P—C18P—C20P | 101 (3) |
C17—C15—H15 | 107.0 | C19P—C18P—H18P | 109.2 |
C2—C15—H15 | 107.0 | C4P—C18P—H18P | 109.2 |
C15—C16—H16A | 109.5 | C20P—C18P—H18P | 109.2 |
C15—C16—H16B | 109.5 | C18P—C19P—H19G | 109.5 |
H16A—C16—H16B | 109.5 | C18P—C19P—H19H | 109.5 |
C15—C16—H16C | 109.5 | H19G—C19P—H19H | 109.5 |
H16A—C16—H16C | 109.5 | C18P—C19P—H19I | 109.5 |
H16B—C16—H16C | 109.5 | H19G—C19P—H19I | 109.5 |
C15—C17—H17A | 109.5 | H19H—C19P—H19I | 109.5 |
C15—C17—H17B | 109.5 | C18P—C20P—H20G | 109.5 |
H17A—C17—H17B | 109.5 | C18P—C20P—H20H | 109.5 |
C15—C17—H17C | 109.5 | H20G—C20P—H20H | 109.5 |
H17A—C17—H17C | 109.5 | C18P—C20P—H20I | 109.5 |
H17B—C17—H17C | 109.5 | H20G—C20P—H20I | 109.5 |
C20—C18—C19 | 111 (3) | H20H—C20P—H20I | 109.5 |
C20—C18—C4 | 110 (2) | C6P—C21P—C23P | 116 (3) |
C19—C18—C4 | 115 (2) | C6P—C21P—C22P | 109 (3) |
C20—C18—H18 | 106.9 | C23P—C21P—C22P | 109 (3) |
C19—C18—H18 | 106.9 | C6P—C21P—H21P | 107.3 |
C4—C18—H18 | 106.9 | C23P—C21P—H21P | 107.3 |
C18—C19—H19A | 109.5 | C22P—C21P—H21P | 107.3 |
C18—C19—H19B | 109.5 | C21P—C22P—H22F | 109.5 |
H19A—C19—H19B | 109.5 | C21P—C22P—H22G | 109.5 |
C18—C19—H19C | 109.5 | H22F—C22P—H22G | 109.5 |
H19A—C19—H19C | 109.5 | C21P—C22P—H22H | 109.5 |
H19B—C19—H19C | 109.5 | H22F—C22P—H22H | 109.5 |
C18—C20—H20A | 109.5 | H22G—C22P—H22H | 109.5 |
C18—C20—H20B | 109.5 | C21P—C23P—H23G | 109.5 |
H20A—C20—H20B | 109.5 | C21P—C23P—H23H | 109.5 |
C18—C20—H20C | 109.5 | H23G—C23P—H23H | 109.5 |
H20A—C20—H20C | 109.5 | C21P—C23P—H23I | 109.5 |
H20B—C20—H20C | 109.5 | H23G—C23P—H23I | 109.5 |
C6—C21—C22 | 112 (2) | H23H—C23P—H23I | 109.5 |
C6—C21—C23 | 112 (2) | C5Z—C6Z—C1Z | 120.0 |
C22—C21—C23 | 106 (2) | C5Z—C6Z—C21Z | 145.8 (18) |
C6—C21—H21 | 108.9 | C1Z—C6Z—C21Z | 93.9 (17) |
C22—C21—H21 | 108.9 | C2Z—C1Z—C6Z | 119.8 |
C23—C21—H21 | 108.9 | C2Z—C1Z—C7Z | 143.4 (17) |
C21—C22—H22A | 109.5 | C6Z—C1Z—C7Z | 95.5 (17) |
C21—C22—H22B | 109.5 | C1Z—C2Z—C3Z | 120.20 (7) |
H22A—C22—H22B | 109.5 | C1Z—C2Z—C15Z | 118 (2) |
C21—C22—H22C | 109.5 | C3Z—C2Z—C15Z | 122 (2) |
H22A—C22—H22C | 109.5 | C4Z—C3Z—C2Z | 119.9 |
H22B—C22—H22C | 109.5 | C4Z—C3Z—H3Z | 120.0 |
C21—C23—H23A | 109.5 | C2Z—C3Z—H3Z | 120.0 |
C21—C23—H23B | 109.5 | C3Z—C4Z—C5Z | 120.0 |
H23A—C23—H23B | 109.5 | C3Z—C4Z—C18Z | 116 (2) |
C21—C23—H23C | 109.5 | C5Z—C4Z—C18Z | 124 (2) |
H23A—C23—H23C | 109.5 | C6Z—C5Z—C4Z | 120.05 (7) |
H23B—C23—H23C | 109.5 | C6Z—C5Z—H5Z | 120.0 |
C2D—C1D—C6D | 123 (2) | C4Z—C5Z—H5Z | 120.0 |
C2D—C1D—C7D | 123 (2) | O1Z—C7Z—C1Z | 97 (3) |
C6D—C1D—C7D | 112.9 (17) | O1Z—C7Z—C8Z | 113 (3) |
C1D—C2D—C3D | 117 (2) | C1Z—C7Z—C8Z | 119 (3) |
C1D—C2D—C15D | 124 (2) | O1Z—C7Z—C21Z | 115 (3) |
C3D—C2D—C15D | 119 (2) | C1Z—C7Z—C21Z | 84.3 (17) |
C2D—C3D—C4D | 122 (2) | C8Z—C7Z—C21Z | 122 (2) |
C2D—C3D—H3D | 118.8 | C13Z—C8Z—C9Z | 120.1 |
C4D—C3D—H3D | 118.8 | C13Z—C8Z—C7Z | 119 (2) |
C5D—C4D—C3D | 117 (2) | C9Z—C8Z—C7Z | 121 (2) |
C5D—C4D—C18D | 113 (2) | C10Z—C9Z—C8Z | 120.0 |
C3D—C4D—C18D | 130 (2) | C10Z—C9Z—H9Z | 119.8 |
C6D—C5D—C4D | 120 (2) | C8Z—C9Z—H9Z | 120.2 |
C6D—C5D—H5D | 119.8 | C9Z—C10Z—C11Z | 119.9 |
C4D—C5D—H5D | 119.8 | C9Z—C10Z—H10Z | 120.4 |
C1D—C6D—C5D | 119 (2) | C11Z—C10Z—H10Z | 119.8 |
C1D—C6D—C21D | 107.7 (17) | C12Z—C11Z—C10Z | 120.4 |
C5D—C6D—C21D | 133 (2) | C12Z—C11Z—C14Z | 118 (2) |
O1D—C7D—C22D | 109 (2) | C10Z—C11Z—C14Z | 122 (2) |
O1D—C7D—C8D | 110 (2) | C11Z—C12Z—C13Z | 119.8 |
C22D—C7D—C8D | 116 (2) | C11Z—C12Z—H12Z | 120.5 |
O1D—C7D—C1D | 108 (2) | C13Z—C12Z—H12Z | 119.7 |
C22D—C7D—C1D | 99.6 (16) | C8Z—C13Z—C12Z | 119.9 |
C8D—C7D—C1D | 114 (2) | C8Z—C13Z—H13Z | 120.1 |
C13D—C8D—C9D | 117.5 (19) | C12Z—C13Z—H13Z | 120.0 |
C13D—C8D—C7D | 123 (2) | O3Z—C14Z—O2Z | 123.9 (7) |
C9D—C8D—C7D | 119.4 (19) | O3Z—C14Z—C11Z | 118.9 (16) |
C10D—C9D—C8D | 120 (2) | O2Z—C14Z—C11Z | 117.2 (16) |
C10D—C9D—H9D | 120.2 | C16Z—C15Z—C17Z | 120 (4) |
C8D—C9D—H9D | 120.2 | C16Z—C15Z—C2Z | 108 (3) |
C9D—C10D—C11D | 123 (2) | C17Z—C15Z—C2Z | 114 (3) |
C9D—C10D—H10D | 118.6 | C16Z—C15Z—H15Z | 104.2 |
C11D—C10D—H10D | 118.6 | C17Z—C15Z—H15Z | 104.2 |
C10D—C11D—C12D | 118 (2) | C2Z—C15Z—H15Z | 104.2 |
C10D—C11D—C14D | 120 (2) | C15Z—C16Z—H16J | 109.5 |
C12D—C11D—C14D | 122 (2) | C15Z—C16Z—H16K | 109.5 |
C13D—C12D—C11D | 118 (3) | H16J—C16Z—H16K | 109.5 |
C13D—C12D—H12D | 120.8 | C15Z—C16Z—H16L | 109.5 |
C11D—C12D—H12D | 120.8 | H16J—C16Z—H16L | 109.5 |
C8D—C13D—C12D | 124 (3) | H16K—C16Z—H16L | 109.5 |
C8D—C13D—H13D | 118.2 | C15Z—C17Z—H17J | 109.5 |
C12D—C13D—H13D | 118.2 | C15Z—C17Z—H17K | 109.5 |
O3D—C14D—O2D | 123.9 (7) | H17J—C17Z—H17K | 109.5 |
O3D—C14D—C11D | 115.3 (13) | C15Z—C17Z—H17L | 109.5 |
O2D—C14D—C11D | 120.7 (13) | H17J—C17Z—H17L | 109.5 |
C16D—C15D—C2D | 112 (2) | H17K—C17Z—H17L | 109.5 |
C16D—C15D—C17D | 114 (3) | C4Z—C18Z—C20Z | 120 (3) |
C2D—C15D—C17D | 112 (2) | C4Z—C18Z—C19Z | 101 (3) |
C16D—C15D—H15D | 106.0 | C20Z—C18Z—C19Z | 111 (3) |
C2D—C15D—H15D | 106.0 | C4Z—C18Z—H18Z | 108.1 |
C17D—C15D—H15D | 106.0 | C20Z—C18Z—H18Z | 108.1 |
C15D—C16D—H16D | 109.5 | C19Z—C18Z—H18Z | 108.1 |
C15D—C16D—H16E | 109.5 | C18Z—C19Z—H19J | 109.5 |
H16D—C16D—H16E | 109.5 | C18Z—C19Z—H19K | 109.5 |
C15D—C16D—H16F | 109.5 | H19J—C19Z—H19K | 109.5 |
H16D—C16D—H16F | 109.5 | C18Z—C19Z—H19L | 109.5 |
H16E—C16D—H16F | 109.5 | H19J—C19Z—H19L | 109.5 |
C15D—C17D—H17D | 109.5 | H19K—C19Z—H19L | 109.5 |
C15D—C17D—H17E | 109.5 | C18Z—C20Z—H20J | 109.5 |
H17D—C17D—H17E | 109.5 | C18Z—C20Z—H20K | 109.5 |
C15D—C17D—H17F | 109.5 | H20J—C20Z—H20K | 109.5 |
H17D—C17D—H17F | 109.5 | C18Z—C20Z—H20L | 109.5 |
H17E—C17D—H17F | 109.5 | H20J—C20Z—H20L | 109.5 |
C19D—C18D—C20D | 120 (2) | H20K—C20Z—H20L | 109.5 |
C19D—C18D—C4D | 119 (2) | C6Z—C21Z—C23Z | 120 (3) |
C20D—C18D—C4D | 116 (3) | C6Z—C21Z—C22Z | 108 (3) |
C19D—C18D—H18D | 96.9 | C23Z—C21Z—C22Z | 112 (3) |
C20D—C18D—H18D | 96.9 | C6Z—C21Z—C7Z | 85.9 (17) |
C4D—C18D—H18D | 96.9 | C23Z—C21Z—C7Z | 114 (3) |
C18D—C19D—H19D | 109.5 | C22Z—C21Z—C7Z | 114 (3) |
C18D—C19D—H19E | 109.5 | C21Z—C22Z—H22I | 109.5 |
H19D—C19D—H19E | 109.5 | C21Z—C22Z—H22J | 109.5 |
C18D—C19D—H19F | 109.5 | H22I—C22Z—H22J | 109.5 |
H19D—C19D—H19F | 109.5 | C21Z—C22Z—H22K | 109.5 |
H19E—C19D—H19F | 109.5 | H22I—C22Z—H22K | 109.5 |
C18D—C20D—H20D | 109.5 | H22J—C22Z—H22K | 109.5 |
C18D—C20D—H20E | 109.5 | C21Z—C23Z—H23J | 109.5 |
H20D—C20D—H20E | 109.5 | C21Z—C23Z—H23K | 109.5 |
C18D—C20D—H20F | 109.5 | H23J—C23Z—H23K | 109.5 |
H20D—C20D—H20F | 109.5 | C21Z—C23Z—H23L | 109.5 |
H20E—C20D—H20F | 109.5 | H23J—C23Z—H23L | 109.5 |
C23D—C21D—C6D | 119 (3) | H23K—C23Z—H23L | 109.5 |
C23D—C21D—C22D | 117 (3) | C25—N1—H1A | 109.5 |
C6D—C21D—C22D | 102.5 (19) | C25—N1—H1B | 109.5 |
C23D—C21D—H21D | 105.9 | H1A—N1—H1B | 109.5 |
C6D—C21D—H21D | 105.9 | C25—N1—H1C | 109.5 |
C22D—C21D—H21D | 105.9 | H1A—N1—H1C | 109.5 |
C7D—C22D—C21D | 107.3 (17) | H1B—N1—H1C | 109.5 |
C7D—C22D—H22D | 110.2 | C25—C24—H24A | 109.5 |
C21D—C22D—H22D | 110.2 | C25—C24—H24B | 109.5 |
C7D—C22D—H22E | 110.2 | H24A—C24—H24B | 109.5 |
C21D—C22D—H22E | 110.2 | C25—C24—H24C | 109.5 |
H22D—C22D—H22E | 108.5 | H24A—C24—H24C | 109.5 |
C21D—C23D—H23D | 109.5 | H24B—C24—H24C | 109.5 |
C21D—C23D—H23E | 109.5 | C26—C25—N1 | 109.4 (6) |
H23D—C23D—H23E | 109.5 | C26—C25—C24 | 115.2 (8) |
C21D—C23D—H23F | 109.5 | N1—C25—C24 | 108.5 (7) |
H23D—C23D—H23F | 109.5 | C26—C25—H25 | 107.8 |
H23E—C23D—H23F | 109.5 | N1—C25—H25 | 107.8 |
C6P—C1P—C2P | 120 (2) | C24—C25—H25 | 107.8 |
C6P—C1P—C7P | 144 (3) | C27—C26—C31 | 118.6 (10) |
C2P—C1P—C7P | 95.8 (19) | C27—C26—C25 | 120.2 (11) |
C3P—C2P—C1P | 120 (2) | C31—C26—C25 | 121.2 (11) |
C3P—C2P—C15P | 145 (3) | C26—C27—C28 | 121.1 (13) |
C1P—C2P—C15P | 93 (2) | C26—C27—H27 | 119.5 |
C4P—C3P—C2P | 119 (3) | C28—C27—H27 | 119.5 |
C4P—C3P—H3P | 120.7 | C29—C28—C27 | 118.8 (18) |
C2P—C3P—H3P | 120.7 | C29—C28—H28 | 120.6 |
C3P—C4P—C5P | 122 (3) | C27—C28—H28 | 120.6 |
C3P—C4P—C18P | 124 (3) | C28—C29—C30 | 121 (2) |
C5P—C4P—C18P | 114 (3) | C28—C29—H29 | 119.3 |
C4P—C5P—C6P | 120 (3) | C30—C29—H29 | 119.3 |
C4P—C5P—H5P | 120.1 | C29—C30—C31 | 119 (2) |
C6P—C5P—H5P | 120.1 | C29—C30—H30 | 120.3 |
C5P—C6P—C1P | 120 (3) | C31—C30—H30 | 120.3 |
C5P—C6P—C21P | 114 (3) | C26—C31—C30 | 120.7 (15) |
C1P—C6P—C21P | 126 (3) | C26—C31—H31 | 119.7 |
O1P—C7P—C1P | 122 (3) | C30—C31—H31 | 119.7 |
O1P—C7P—C8P | 106 (2) |
C31H39NO3 | Dx = 1.121 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 2080 reflections |
a = 6.3696 (5) Å | θ = 1.6–18.8° |
b = 13.4941 (10) Å | µ = 0.07 mm−1 |
c = 32.6553 (15) Å | T = 299 K |
V = 2806.8 (3) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.12 × 0.10 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 5426 independent reflections |
Radiation source: fine-focus sealed tube | 1914 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.135 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −14→16 |
Tmin = 0.843, Tmax = 1.000 | l = −40→40 |
25014 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.094 | H-atom parameters constrained |
wR(F2) = 0.182 | w = 1/[σ2(Fo2) + (0.0212P)2 + 1.2062P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
5426 reflections | Δρmax = 0.13 e Å−3 |
476 parameters | Δρmin = −0.15 e Å−3 |
557 restraints | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 1.2 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 1.043 (5) | 0.243 (2) | 0.6356 (12) | 0.079 (8) | 0.329 (4) |
O2 | 0.6520 (10) | 0.6320 (4) | 0.51798 (16) | 0.0819 (18) | 0.329 (4) |
O3 | 0.3506 (11) | 0.6158 (5) | 0.54976 (17) | 0.096 (2) | 0.329 (4) |
C1 | 0.813 (8) | 0.284 (3) | 0.6915 (8) | 0.065 (11)* | 0.329 (4) |
C2 | 0.853 (6) | 0.348 (2) | 0.7237 (9) | 0.062 (10)* | 0.329 (4) |
C3 | 0.796 (6) | 0.325 (3) | 0.7640 (9) | 0.076 (10)* | 0.329 (4) |
H3 | 0.8315 | 0.3675 | 0.7852 | 0.091* | 0.329 (4) |
C4 | 0.686 (5) | 0.238 (2) | 0.7722 (7) | 0.054 (9)* | 0.329 (4) |
C5 | 0.637 (6) | 0.178 (2) | 0.7393 (7) | 0.062 (9)* | 0.329 (4) |
H5 | 0.5605 | 0.1201 | 0.7441 | 0.075* | 0.329 (4) |
C6 | 0.696 (6) | 0.200 (2) | 0.6993 (8) | 0.062 (10)* | 0.329 (4) |
C7 | 0.904 (5) | 0.295 (2) | 0.6488 (8) | 0.072 (9)* | 0.329 (4) |
C8 | 0.801 (5) | 0.368 (2) | 0.6208 (8) | 0.051 (10)* | 0.329 (4) |
C9 | 0.923 (4) | 0.4083 (18) | 0.5905 (7) | 0.047 (7)* | 0.329 (4) |
H9 | 1.0613 | 0.3885 | 0.5864 | 0.057* | 0.329 (4) |
C10 | 0.830 (5) | 0.4798 (19) | 0.5666 (9) | 0.055 (8)* | 0.329 (4) |
H10 | 0.9085 | 0.5070 | 0.5454 | 0.066* | 0.329 (4) |
C11 | 0.631 (5) | 0.513 (2) | 0.5717 (9) | 0.059 (11)* | 0.329 (4) |
C12 | 0.509 (6) | 0.467 (2) | 0.6016 (9) | 0.060 (9)* | 0.329 (4) |
H12 | 0.3689 | 0.4849 | 0.6049 | 0.072* | 0.329 (4) |
C13 | 0.597 (6) | 0.394 (2) | 0.6264 (10) | 0.063 (10)* | 0.329 (4) |
H13 | 0.5175 | 0.3642 | 0.6467 | 0.076* | 0.329 (4) |
C14 | 0.5366 (16) | 0.5933 (6) | 0.5449 (2) | 0.071 (2) | 0.329 (4) |
C15 | 1.010 (5) | 0.434 (2) | 0.7170 (12) | 0.079 (10)* | 0.329 (4) |
H15 | 1.0164 | 0.4449 | 0.6874 | 0.094* | 0.329 (4) |
C16 | 1.230 (5) | 0.406 (4) | 0.730 (2) | 0.11 (2)* | 0.329 (4) |
H16A | 1.2699 | 0.3453 | 0.7171 | 0.164* | 0.329 (4) |
H16B | 1.3250 | 0.4579 | 0.7221 | 0.164* | 0.329 (4) |
H16C | 1.2337 | 0.3983 | 0.7592 | 0.164* | 0.329 (4) |
C17 | 0.932 (6) | 0.529 (2) | 0.7358 (11) | 0.114 (13)* | 0.329 (4) |
H17A | 0.7923 | 0.5419 | 0.7263 | 0.172* | 0.329 (4) |
H17B | 0.9317 | 0.5227 | 0.7651 | 0.172* | 0.329 (4) |
H17C | 1.0230 | 0.5823 | 0.7279 | 0.172* | 0.329 (4) |
C18 | 0.635 (5) | 0.210 (3) | 0.8175 (7) | 0.077 (10)* | 0.329 (4) |
H18 | 0.6512 | 0.1376 | 0.8200 | 0.092* | 0.329 (4) |
C19 | 0.782 (6) | 0.257 (3) | 0.8484 (9) | 0.072 (11)* | 0.329 (4) |
H19A | 0.9249 | 0.2408 | 0.8414 | 0.108* | 0.329 (4) |
H19B | 0.7644 | 0.3274 | 0.8480 | 0.108* | 0.329 (4) |
H19C | 0.7517 | 0.2320 | 0.8753 | 0.108* | 0.329 (4) |
C20 | 0.414 (6) | 0.233 (4) | 0.8275 (16) | 0.115 (17)* | 0.329 (4) |
H20A | 0.3237 | 0.2022 | 0.8076 | 0.172* | 0.329 (4) |
H20B | 0.3815 | 0.2078 | 0.8542 | 0.172* | 0.329 (4) |
H20C | 0.3941 | 0.3032 | 0.8270 | 0.172* | 0.329 (4) |
C21 | 0.649 (5) | 0.129 (2) | 0.6646 (9) | 0.074 (10)* | 0.329 (4) |
H21 | 0.6329 | 0.1661 | 0.6390 | 0.089* | 0.329 (4) |
C22 | 0.825 (5) | 0.055 (2) | 0.6603 (13) | 0.109 (13)* | 0.329 (4) |
H22A | 0.7944 | 0.0103 | 0.6382 | 0.164* | 0.329 (4) |
H22B | 0.9537 | 0.0894 | 0.6547 | 0.164* | 0.329 (4) |
H22C | 0.8392 | 0.0182 | 0.6853 | 0.164* | 0.329 (4) |
C23 | 0.439 (5) | 0.073 (2) | 0.6746 (12) | 0.082 (11)* | 0.329 (4) |
H23A | 0.3270 | 0.1200 | 0.6773 | 0.123* | 0.329 (4) |
H23B | 0.4072 | 0.0275 | 0.6528 | 0.123* | 0.329 (4) |
H23C | 0.4549 | 0.0369 | 0.6998 | 0.123* | 0.329 (4) |
O1D | 1.096 (4) | 0.271 (3) | 0.6401 (12) | 0.075 (9) | 0.338 (4) |
O2D | 0.6520 (10) | 0.6320 (4) | 0.51798 (16) | 0.0819 (18) | 0.338 (4) |
O3D | 0.3506 (11) | 0.6158 (5) | 0.54976 (17) | 0.096 (2) | 0.338 (4) |
C1D | 0.807 (7) | 0.279 (3) | 0.6910 (7) | 0.062 (10)* | 0.338 (4) |
C2D | 0.897 (5) | 0.342 (2) | 0.7183 (7) | 0.055 (8)* | 0.338 (4) |
C3D | 0.843 (5) | 0.333 (2) | 0.7596 (8) | 0.066 (8)* | 0.338 (4) |
H3D | 0.9074 | 0.3739 | 0.7787 | 0.079* | 0.338 (4) |
C4D | 0.692 (6) | 0.262 (3) | 0.7730 (8) | 0.070 (10)* | 0.338 (4) |
C5D | 0.601 (7) | 0.200 (3) | 0.7435 (8) | 0.061 (10)* | 0.338 (4) |
H5D | 0.5012 | 0.1534 | 0.7513 | 0.074* | 0.338 (4) |
C6D | 0.662 (8) | 0.208 (3) | 0.7027 (8) | 0.059 (10)* | 0.338 (4) |
C7D | 0.869 (4) | 0.2717 (18) | 0.6448 (7) | 0.079 (10)* | 0.338 (4) |
C8D | 0.775 (5) | 0.358 (2) | 0.6202 (9) | 0.061 (10)* | 0.338 (4) |
C9D | 0.878 (5) | 0.385 (2) | 0.5842 (8) | 0.061 (9)* | 0.338 (4) |
H9D | 1.0027 | 0.3542 | 0.5767 | 0.073* | 0.338 (4) |
C10D | 0.794 (4) | 0.459 (2) | 0.5602 (9) | 0.059 (9)* | 0.338 (4) |
H10D | 0.8642 | 0.4760 | 0.5363 | 0.071* | 0.338 (4) |
C11D | 0.610 (4) | 0.5079 (18) | 0.5695 (9) | 0.061 (10)* | 0.338 (4) |
C12D | 0.510 (6) | 0.479 (3) | 0.6056 (10) | 0.069 (11)* | 0.338 (4) |
H12D | 0.3859 | 0.5100 | 0.6133 | 0.083* | 0.338 (4) |
C13D | 0.594 (6) | 0.405 (3) | 0.6303 (11) | 0.060 (10)* | 0.338 (4) |
H13D | 0.5243 | 0.3872 | 0.6542 | 0.073* | 0.338 (4) |
C14D | 0.5366 (16) | 0.5933 (6) | 0.5449 (2) | 0.071 (2) | 0.338 (4) |
C15D | 1.036 (5) | 0.429 (2) | 0.7057 (11) | 0.080 (10)* | 0.338 (4) |
H15D | 1.0603 | 0.4253 | 0.6761 | 0.096* | 0.338 (4) |
C16D | 1.239 (4) | 0.425 (3) | 0.7269 (17) | 0.058 (11)* | 0.338 (4) |
H16D | 1.3238 | 0.4797 | 0.7186 | 0.087* | 0.338 (4) |
H16E | 1.2161 | 0.4274 | 0.7560 | 0.087* | 0.338 (4) |
H16F | 1.3090 | 0.3638 | 0.7201 | 0.087* | 0.338 (4) |
C17D | 0.919 (5) | 0.5273 (19) | 0.7157 (12) | 0.055 (9)* | 0.338 (4) |
H17D | 0.7869 | 0.5287 | 0.7016 | 0.082* | 0.338 (4) |
H17E | 0.8949 | 0.5314 | 0.7447 | 0.082* | 0.338 (4) |
H17F | 1.0032 | 0.5825 | 0.7071 | 0.082* | 0.338 (4) |
C18D | 0.625 (6) | 0.240 (3) | 0.8178 (8) | 0.094 (11)* | 0.338 (4) |
H18D | 0.5977 | 0.1701 | 0.8118 | 0.113* | 0.338 (4) |
C19D | 0.776 (6) | 0.216 (2) | 0.8508 (9) | 0.102 (13)* | 0.338 (4) |
H19D | 0.9124 | 0.2049 | 0.8392 | 0.153* | 0.338 (4) |
H19E | 0.7824 | 0.2698 | 0.8699 | 0.153* | 0.338 (4) |
H19F | 0.7304 | 0.1570 | 0.8648 | 0.153* | 0.338 (4) |
C20D | 0.402 (6) | 0.260 (4) | 0.8279 (15) | 0.096 (16)* | 0.338 (4) |
H20D | 0.3261 | 0.2746 | 0.8032 | 0.144* | 0.338 (4) |
H20E | 0.3418 | 0.2032 | 0.8409 | 0.144* | 0.338 (4) |
H20F | 0.3938 | 0.3161 | 0.8460 | 0.144* | 0.338 (4) |
C21D | 0.597 (6) | 0.151 (2) | 0.6644 (9) | 0.078 (10)* | 0.338 (4) |
H21D | 0.4741 | 0.1845 | 0.6529 | 0.094* | 0.338 (4) |
C22D | 0.783 (4) | 0.1704 (16) | 0.6351 (7) | 0.080 (8)* | 0.338 (4) |
H22D | 0.8903 | 0.1205 | 0.6388 | 0.096* | 0.338 (4) |
H22E | 0.7352 | 0.1680 | 0.6069 | 0.096* | 0.338 (4) |
C23D | 0.539 (6) | 0.044 (2) | 0.6699 (10) | 0.126 (14)* | 0.338 (4) |
H23D | 0.5007 | 0.0164 | 0.6438 | 0.189* | 0.338 (4) |
H23E | 0.6558 | 0.0087 | 0.6810 | 0.189* | 0.338 (4) |
H23F | 0.4215 | 0.0395 | 0.6883 | 0.189* | 0.338 (4) |
O1P | 1.114 (7) | 0.301 (3) | 0.6508 (16) | 0.078 (9) | 0.204 (4) |
O2P | 0.6520 (10) | 0.6320 (4) | 0.51798 (16) | 0.0819 (18) | 0.204 (4) |
O3P | 0.3506 (11) | 0.6158 (5) | 0.54976 (17) | 0.096 (2) | 0.204 (4) |
C1P | 0.804 (7) | 0.291 (3) | 0.7004 (10) | 0.054 (11)* | 0.204 (4) |
C2P | 0.868 (7) | 0.348 (3) | 0.7344 (10) | 0.060 (12)* | 0.204 (4) |
C3P | 0.787 (8) | 0.325 (4) | 0.7732 (11) | 0.073 (12)* | 0.204 (4) |
H3P | 0.8258 | 0.3606 | 0.7963 | 0.088* | 0.204 (4) |
C4P | 0.648 (7) | 0.246 (4) | 0.7758 (10) | 0.064 (12)* | 0.204 (4) |
C5P | 0.581 (10) | 0.190 (5) | 0.7428 (11) | 0.057 (13)* | 0.204 (4) |
H5P | 0.4857 | 0.1387 | 0.7462 | 0.068* | 0.204 (4) |
C6P | 0.662 (10) | 0.213 (4) | 0.7042 (11) | 0.057 (13)* | 0.204 (4) |
C7P | 0.939 (5) | 0.3451 (18) | 0.6697 (7) | 0.069 (10)* | 0.204 (4) |
C8P | 0.838 (5) | 0.4082 (17) | 0.6362 (7) | 0.056 (9)* | 0.204 (4) |
C9P | 0.955 (5) | 0.450 (2) | 0.6055 (8) | 0.072 (11)* | 0.204 (4) |
H9P | 1.0992 | 0.4380 | 0.6046 | 0.086* | 0.204 (4) |
C10P | 0.862 (5) | 0.509 (2) | 0.5755 (9) | 0.072 (12)* | 0.204 (4) |
H10P | 0.9453 | 0.5359 | 0.5548 | 0.086* | 0.204 (4) |
C11P | 0.650 (5) | 0.5292 (12) | 0.5761 (7) | 0.059 (12)* | 0.204 (4) |
C12P | 0.529 (6) | 0.488 (3) | 0.6077 (10) | 0.062 (12)* | 0.204 (4) |
H12P | 0.3860 | 0.5011 | 0.6090 | 0.075* | 0.204 (4) |
C13P | 0.624 (5) | 0.429 (3) | 0.6370 (10) | 0.058 (11)* | 0.204 (4) |
H13P | 0.5426 | 0.4020 | 0.6578 | 0.069* | 0.204 (4) |
C14P | 0.5366 (16) | 0.5933 (6) | 0.5449 (2) | 0.071 (2) | 0.204 (4) |
C15P | 0.995 (6) | 0.419 (2) | 0.7091 (10) | 0.072 (13)* | 0.204 (4) |
C16P | 1.230 (6) | 0.429 (5) | 0.7125 (16) | 0.11 (2)* | 0.204 (4) |
H16G | 1.2785 | 0.4788 | 0.6936 | 0.163* | 0.204 (4) |
H16H | 1.2666 | 0.4486 | 0.7399 | 0.163* | 0.204 (4) |
H16I | 1.2958 | 0.3670 | 0.7062 | 0.163* | 0.204 (4) |
C17P | 0.913 (10) | 0.524 (3) | 0.7024 (17) | 0.12 (2)* | 0.204 (4) |
H17G | 1.0105 | 0.5607 | 0.6857 | 0.177* | 0.204 (4) |
H17H | 0.7790 | 0.5219 | 0.6889 | 0.177* | 0.204 (4) |
H17I | 0.8979 | 0.5570 | 0.7284 | 0.177* | 0.204 (4) |
C18P | 0.558 (6) | 0.215 (4) | 0.8171 (10) | 0.078 (12)* | 0.204 (4) |
H18P | 0.5581 | 0.1432 | 0.8203 | 0.094* | 0.204 (4) |
C19P | 0.684 (7) | 0.266 (4) | 0.8511 (13) | 0.081 (16)* | 0.204 (4) |
H19G | 0.8234 | 0.2392 | 0.8517 | 0.122* | 0.204 (4) |
H19H | 0.6894 | 0.3357 | 0.8461 | 0.122* | 0.204 (4) |
H19I | 0.6164 | 0.2538 | 0.8770 | 0.122* | 0.204 (4) |
C20P | 0.336 (5) | 0.257 (4) | 0.8159 (14) | 0.065 (14)* | 0.204 (4) |
H20G | 0.2655 | 0.2412 | 0.8410 | 0.097* | 0.204 (4) |
H20H | 0.3418 | 0.3274 | 0.8125 | 0.097* | 0.204 (4) |
H20I | 0.2615 | 0.2279 | 0.7933 | 0.097* | 0.204 (4) |
C21P | 0.576 (7) | 0.149 (3) | 0.6701 (13) | 0.070 (12)* | 0.204 (4) |
H21P | 0.5544 | 0.1908 | 0.6459 | 0.084* | 0.204 (4) |
C22P | 0.731 (8) | 0.066 (4) | 0.6584 (17) | 0.088 (15)* | 0.204 (4) |
H22F | 0.6719 | 0.0266 | 0.6368 | 0.132* | 0.204 (4) |
H22G | 0.8606 | 0.0947 | 0.6494 | 0.132* | 0.204 (4) |
H22H | 0.7567 | 0.0248 | 0.6819 | 0.132* | 0.204 (4) |
C23P | 0.367 (7) | 0.097 (4) | 0.6801 (18) | 0.107 (19)* | 0.204 (4) |
H23G | 0.3238 | 0.0580 | 0.6570 | 0.161* | 0.204 (4) |
H23H | 0.3853 | 0.0551 | 0.7035 | 0.161* | 0.204 (4) |
H23I | 0.2620 | 0.1462 | 0.6859 | 0.161* | 0.204 (4) |
O1Z | 1.117 (7) | 0.281 (6) | 0.653 (2) | 0.077 (11)* | 0.128 (4) |
O2Z | 0.6520 (10) | 0.6320 (4) | 0.51798 (16) | 0.0819 (18) | 0.128 (4) |
O3Z | 0.3506 (11) | 0.6158 (5) | 0.54976 (17) | 0.096 (2) | 0.128 (4) |
C6Z | 0.761 (7) | 0.219 (3) | 0.7070 (9) | 0.051 (13)* | 0.128 (4) |
C1Z | 0.881 (6) | 0.303 (3) | 0.6993 (9) | 0.053 (13)* | 0.128 (4) |
C2Z | 0.916 (7) | 0.372 (3) | 0.7302 (11) | 0.069 (14)* | 0.128 (4) |
C3Z | 0.831 (7) | 0.357 (3) | 0.7689 (10) | 0.080 (14)* | 0.128 (4) |
H3Z | 0.8554 | 0.4036 | 0.7901 | 0.096* | 0.128 (4) |
C4Z | 0.712 (6) | 0.273 (3) | 0.7767 (9) | 0.067 (14)* | 0.128 (4) |
C5Z | 0.676 (7) | 0.204 (3) | 0.7458 (10) | 0.061 (14)* | 0.128 (4) |
H5Z | 0.5941 | 0.1469 | 0.7511 | 0.073* | 0.128 (4) |
C7Z | 0.895 (7) | 0.289 (3) | 0.6533 (10) | 0.077 (15)* | 0.128 (4) |
C8Z | 0.809 (8) | 0.370 (3) | 0.6245 (13) | 0.051 (14)* | 0.128 (4) |
C9Z | 0.899 (10) | 0.386 (5) | 0.5862 (17) | 0.059 (14)* | 0.128 (4) |
H9Z | 1.0168 | 0.3483 | 0.5778 | 0.070* | 0.128 (4) |
C10Z | 0.814 (10) | 0.456 (5) | 0.5601 (14) | 0.064 (15)* | 0.128 (4) |
H10Z | 0.8748 | 0.4678 | 0.5340 | 0.077* | 0.128 (4) |
C11Z | 0.640 (5) | 0.5115 (16) | 0.5725 (10) | 0.056 (14)* | 0.128 (4) |
C12Z | 0.551 (7) | 0.496 (3) | 0.6106 (13) | 0.055 (13)* | 0.128 (4) |
H12Z | 0.4326 | 0.5333 | 0.6191 | 0.066* | 0.128 (4) |
C13Z | 0.635 (8) | 0.425 (4) | 0.6367 (12) | 0.058 (14)* | 0.128 (4) |
H13Z | 0.5746 | 0.4138 | 0.6629 | 0.070* | 0.128 (4) |
C14Z | 0.5366 (16) | 0.5933 (6) | 0.5449 (2) | 0.071 (2) | 0.128 (4) |
C15Z | 1.042 (8) | 0.461 (3) | 0.719 (2) | 0.078 (14)* | 0.128 (4) |
H15Z | 1.0703 | 0.4551 | 0.6901 | 0.094* | 0.128 (4) |
C16Z | 1.249 (8) | 0.452 (5) | 0.739 (2) | 0.11 (3)* | 0.128 (4) |
H16J | 1.3064 | 0.3877 | 0.7337 | 0.165* | 0.128 (4) |
H16K | 1.3413 | 0.5022 | 0.7292 | 0.165* | 0.128 (4) |
H16L | 1.2327 | 0.4596 | 0.7685 | 0.165* | 0.128 (4) |
C17Z | 0.919 (12) | 0.553 (4) | 0.724 (3) | 0.10 (3)* | 0.128 (4) |
H17J | 0.7892 | 0.5467 | 0.7088 | 0.147* | 0.128 (4) |
H17K | 0.8889 | 0.5653 | 0.7520 | 0.147* | 0.128 (4) |
H17L | 0.9975 | 0.6079 | 0.7126 | 0.147* | 0.128 (4) |
C18Z | 0.624 (9) | 0.261 (5) | 0.8194 (12) | 0.087 (15)* | 0.128 (4) |
H18Z | 0.6096 | 0.1906 | 0.8262 | 0.105* | 0.128 (4) |
C19Z | 0.800 (11) | 0.307 (6) | 0.8445 (17) | 0.10 (2)* | 0.128 (4) |
H19J | 0.7640 | 0.3048 | 0.8730 | 0.147* | 0.128 (4) |
H19K | 0.9277 | 0.2714 | 0.8399 | 0.147* | 0.128 (4) |
H19L | 0.8183 | 0.3751 | 0.8363 | 0.147* | 0.128 (4) |
C20Z | 0.420 (9) | 0.316 (6) | 0.829 (2) | 0.10 (2)* | 0.128 (4) |
H20J | 0.3787 | 0.3032 | 0.8564 | 0.145* | 0.128 (4) |
H20K | 0.4408 | 0.3857 | 0.8248 | 0.145* | 0.128 (4) |
H20L | 0.3119 | 0.2931 | 0.8104 | 0.145* | 0.128 (4) |
C21Z | 0.765 (7) | 0.186 (3) | 0.6629 (10) | 0.077 (14)* | 0.128 (4) |
C22Z | 0.903 (10) | 0.095 (4) | 0.659 (2) | 0.10 (2)* | 0.128 (4) |
H22I | 0.9061 | 0.0730 | 0.6312 | 0.154* | 0.128 (4) |
H22J | 1.0427 | 0.1103 | 0.6681 | 0.154* | 0.128 (4) |
H22K | 0.8469 | 0.0426 | 0.6761 | 0.154* | 0.128 (4) |
C23Z | 0.562 (9) | 0.174 (5) | 0.639 (2) | 0.14 (3)* | 0.128 (4) |
H23J | 0.5931 | 0.1525 | 0.6117 | 0.206* | 0.128 (4) |
H23K | 0.4742 | 0.1265 | 0.6523 | 0.206* | 0.128 (4) |
H23L | 0.4911 | 0.2370 | 0.6379 | 0.206* | 0.128 (4) |
N1 | 0.0595 (9) | 0.6667 (4) | 0.49226 (17) | 0.0657 (19) | |
H1A | 0.1617 | 0.6456 | 0.5087 | 0.079* | |
H1B | −0.0643 | 0.6492 | 0.5026 | 0.079* | |
H1C | 0.0657 | 0.7324 | 0.4901 | 0.079* | |
C24 | 0.2976 (16) | 0.6512 (7) | 0.4330 (2) | 0.105 (4) | |
H24A | 0.4066 | 0.6330 | 0.4518 | 0.158* | |
H24B | 0.2997 | 0.7216 | 0.4288 | 0.158* | |
H24C | 0.3201 | 0.6181 | 0.4073 | 0.158* | |
C25 | 0.0856 (15) | 0.6207 (7) | 0.4504 (2) | 0.078 (3) | |
H25 | −0.0237 | 0.6480 | 0.4325 | 0.094* | |
C26 | 0.051 (2) | 0.5115 (9) | 0.4535 (3) | 0.087 (3) | |
C27 | −0.136 (2) | 0.4715 (11) | 0.4395 (3) | 0.112 (4) | |
H27 | −0.2408 | 0.5127 | 0.4294 | 0.134* | |
C28 | −0.167 (3) | 0.3686 (14) | 0.4408 (5) | 0.155 (6) | |
H28 | −0.2919 | 0.3414 | 0.4313 | 0.186* | |
C29 | −0.014 (4) | 0.3090 (15) | 0.4558 (6) | 0.187 (11) | |
H29 | −0.0366 | 0.2410 | 0.4573 | 0.225* | |
C30 | 0.174 (4) | 0.3480 (14) | 0.4690 (5) | 0.179 (8) | |
H30 | 0.2811 | 0.3066 | 0.4781 | 0.215* | |
C31 | 0.202 (2) | 0.4499 (11) | 0.4684 (3) | 0.127 (5) | |
H31 | 0.3262 | 0.4767 | 0.4784 | 0.152* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.086 (15) | 0.070 (15) | 0.082 (12) | 0.024 (13) | 0.019 (12) | 0.011 (12) |
O2 | 0.078 (4) | 0.095 (4) | 0.072 (4) | 0.004 (4) | 0.009 (3) | 0.031 (3) |
O3 | 0.076 (5) | 0.145 (6) | 0.068 (4) | 0.024 (5) | −0.006 (4) | 0.031 (4) |
C14 | 0.097 (7) | 0.072 (5) | 0.044 (5) | −0.004 (6) | −0.011 (6) | 0.008 (4) |
O1D | 0.076 (13) | 0.073 (18) | 0.075 (14) | 0.002 (13) | 0.015 (13) | 0.012 (14) |
O2D | 0.078 (4) | 0.095 (4) | 0.072 (4) | 0.004 (4) | 0.009 (3) | 0.031 (3) |
O3D | 0.076 (5) | 0.145 (6) | 0.068 (4) | 0.024 (5) | −0.006 (4) | 0.031 (4) |
C14D | 0.097 (7) | 0.072 (5) | 0.044 (5) | −0.004 (6) | −0.011 (6) | 0.008 (4) |
O1P | 0.076 (15) | 0.078 (18) | 0.079 (16) | 0.006 (14) | 0.020 (14) | 0.014 (14) |
O2P | 0.078 (4) | 0.095 (4) | 0.072 (4) | 0.004 (4) | 0.009 (3) | 0.031 (3) |
O3P | 0.076 (5) | 0.145 (6) | 0.068 (4) | 0.024 (5) | −0.006 (4) | 0.031 (4) |
C14P | 0.097 (7) | 0.072 (5) | 0.044 (5) | −0.004 (6) | −0.011 (6) | 0.008 (4) |
O2Z | 0.078 (4) | 0.095 (4) | 0.072 (4) | 0.004 (4) | 0.009 (3) | 0.031 (3) |
O3Z | 0.076 (5) | 0.145 (6) | 0.068 (4) | 0.024 (5) | −0.006 (4) | 0.031 (4) |
C14Z | 0.097 (7) | 0.072 (5) | 0.044 (5) | −0.004 (6) | −0.011 (6) | 0.008 (4) |
N1 | 0.064 (5) | 0.080 (4) | 0.053 (4) | 0.010 (4) | 0.001 (4) | 0.014 (4) |
C24 | 0.108 (9) | 0.142 (9) | 0.066 (6) | 0.000 (8) | 0.031 (6) | 0.006 (6) |
C25 | 0.084 (8) | 0.098 (8) | 0.053 (6) | 0.011 (6) | −0.013 (5) | 0.006 (5) |
C26 | 0.110 (10) | 0.105 (9) | 0.046 (6) | 0.004 (9) | −0.005 (6) | −0.010 (6) |
C27 | 0.124 (12) | 0.126 (12) | 0.085 (8) | 0.000 (10) | 0.020 (8) | −0.018 (7) |
C28 | 0.186 (19) | 0.138 (15) | 0.141 (13) | −0.049 (14) | 0.030 (13) | −0.027 (12) |
C29 | 0.29 (4) | 0.112 (15) | 0.155 (18) | −0.027 (18) | 0.06 (2) | −0.006 (12) |
C30 | 0.25 (3) | 0.108 (15) | 0.177 (15) | 0.032 (14) | −0.011 (16) | 0.001 (11) |
C31 | 0.170 (15) | 0.106 (10) | 0.105 (9) | 0.009 (11) | −0.024 (9) | −0.006 (8) |
O1—C7 | 1.21 (2) | C4P—C18P | 1.52 (2) |
O2—C14 | 1.259 (9) | C5P—C6P | 1.40 (2) |
O3—C14 | 1.233 (10) | C5P—H5P | 0.9300 |
C1—C2 | 1.38 (2) | C6P—C21P | 1.51 (2) |
C1—C6 | 1.39 (2) | C7P—C8P | 1.53 (2) |
C1—C7 | 1.52 (2) | C7P—C15P | 1.66 (2) |
C2—C3 | 1.40 (2) | C8P—C9P | 1.37 (2) |
C2—C15 | 1.54 (2) | C8P—C13P | 1.39 (2) |
C3—C4 | 1.39 (2) | C9P—C10P | 1.40 (2) |
C3—H3 | 0.9300 | C9P—H9P | 0.9300 |
C4—C5 | 1.38 (2) | C10P—C11P | 1.38 (2) |
C4—C18 | 1.56 (2) | C10P—H10P | 0.9300 |
C5—C6 | 1.39 (2) | C11P—C12P | 1.40 (2) |
C5—H5 | 0.9300 | C11P—C14P | 1.52 (2) |
C6—C21 | 1.51 (2) | C12P—C13P | 1.39 (2) |
C7—C8 | 1.50 (2) | C12P—H12P | 0.9300 |
C8—C13 | 1.36 (2) | C13P—H13P | 0.9300 |
C8—C9 | 1.37 (2) | C15P—C16P | 1.51 (2) |
C9—C10 | 1.38 (2) | C15P—C17P | 1.53 (2) |
C9—H9 | 0.9300 | C16P—H16G | 0.9600 |
C10—C11 | 1.35 (2) | C16P—H16H | 0.9600 |
C10—H10 | 0.9300 | C16P—H16I | 0.9600 |
C11—C12 | 1.39 (2) | C17P—H17G | 0.9600 |
C11—C14 | 1.515 (19) | C17P—H17H | 0.9600 |
C12—C13 | 1.39 (2) | C17P—H17I | 0.9600 |
C12—H12 | 0.9300 | C18P—C20P | 1.52 (3) |
C13—H13 | 0.9300 | C18P—C19P | 1.53 (3) |
C15—C16 | 1.50 (2) | C18P—H18P | 0.9800 |
C15—C17 | 1.51 (2) | C19P—H19G | 0.9600 |
C15—H15 | 0.9800 | C19P—H19H | 0.9600 |
C16—H16A | 0.9600 | C19P—H19I | 0.9600 |
C16—H16B | 0.9600 | C20P—H20G | 0.9600 |
C16—H16C | 0.9600 | C20P—H20H | 0.9600 |
C17—H17A | 0.9600 | C20P—H20I | 0.9600 |
C17—H17B | 0.9600 | C21P—C23P | 1.54 (3) |
C17—H17C | 0.9600 | C21P—C22P | 1.54 (3) |
C18—C20 | 1.47 (2) | C21P—H21P | 0.9800 |
C18—C19 | 1.52 (2) | C22P—H22F | 0.9600 |
C18—H18 | 0.9800 | C22P—H22G | 0.9600 |
C19—H19A | 0.9600 | C22P—H22H | 0.9600 |
C19—H19B | 0.9600 | C23P—H23G | 0.9600 |
C19—H19C | 0.9600 | C23P—H23H | 0.9600 |
C20—H20A | 0.9600 | C23P—H23I | 0.9600 |
C20—H20B | 0.9600 | O1Z—C7Z | 1.42 (3) |
C20—H20C | 0.9600 | O2Z—C14Z | 1.259 (9) |
C21—C22 | 1.51 (2) | O3Z—C14Z | 1.233 (10) |
C21—C23 | 1.57 (2) | C6Z—C5Z | 1.3889 |
C21—H21 | 0.9800 | C6Z—C1Z | 1.3908 |
C22—H22A | 0.9600 | C6Z—C21Z | 1.51 (2) |
C22—H22B | 0.9600 | C1Z—C2Z | 1.3877 |
C22—H22C | 0.9600 | C1Z—C7Z | 1.52 (2) |
C23—H23A | 0.9600 | C2Z—C3Z | 1.3891 |
C23—H23B | 0.9600 | C2Z—C15Z | 1.49 (2) |
C23—H23C | 0.9600 | C3Z—C4Z | 1.3873 |
O1D—C7D | 1.45 (2) | C3Z—H3Z | 0.9495 |
O2D—C14D | 1.259 (9) | C4Z—C5Z | 1.3887 |
O3D—C14D | 1.233 (10) | C4Z—C18Z | 1.51 (2) |
C1D—C2D | 1.36 (2) | C5Z—H5Z | 0.9499 |
C1D—C6D | 1.38 (2) | C7Z—C8Z | 1.54 (2) |
C1D—C7D | 1.56 (2) | C7Z—C21Z | 1.65 (2) |
C2D—C3D | 1.40 (2) | C8Z—C13Z | 1.3903 |
C2D—C15D | 1.53 (2) | C8Z—C9Z | 1.3916 |
C3D—C4D | 1.42 (2) | C9Z—C10Z | 1.3863 |
C3D—H3D | 0.9300 | C9Z—H9Z | 0.9482 |
C4D—C5D | 1.40 (2) | C10Z—C11Z | 1.3916 |
C4D—C18D | 1.55 (2) | C10Z—H10Z | 0.9500 |
C5D—C6D | 1.39 (2) | C11Z—C12Z | 1.3864 |
C5D—H5D | 0.9300 | C11Z—C14Z | 1.571 (19) |
C6D—C21D | 1.53 (2) | C12Z—C13Z | 1.3935 |
C7D—C22D | 1.51 (2) | C12Z—H12Z | 0.9479 |
C7D—C8D | 1.54 (2) | C13Z—H13Z | 0.9477 |
C8D—C13D | 1.36 (2) | C15Z—C17Z | 1.47 (3) |
C8D—C9D | 1.39 (2) | C15Z—C16Z | 1.48 (3) |
C9D—C10D | 1.373 (19) | C15Z—H15Z | 0.9800 |
C9D—H9D | 0.9300 | C16Z—H16J | 0.9600 |
C10D—C11D | 1.38 (2) | C16Z—H16K | 0.9600 |
C10D—H10D | 0.9300 | C16Z—H16L | 0.9600 |
C11D—C12D | 1.39 (2) | C17Z—H17J | 0.9600 |
C11D—C14D | 1.481 (18) | C17Z—H17K | 0.9600 |
C12D—C13D | 1.39 (2) | C17Z—H17L | 0.9600 |
C12D—H12D | 0.9300 | C18Z—C19Z | 1.52 (3) |
C13D—H13D | 0.9300 | C18Z—C20Z | 1.53 (3) |
C15D—C16D | 1.47 (2) | C18Z—H18Z | 0.9800 |
C15D—C17D | 1.56 (2) | C19Z—H19J | 0.9600 |
C15D—H15D | 0.9800 | C19Z—H19K | 0.9600 |
C16D—H16D | 0.9600 | C19Z—H19L | 0.9600 |
C16D—H16E | 0.9600 | C20Z—H20J | 0.9600 |
C16D—H16F | 0.9600 | C20Z—H20K | 0.9600 |
C17D—H17D | 0.9600 | C20Z—H20L | 0.9600 |
C17D—H17E | 0.9600 | C21Z—C22Z | 1.51 (2) |
C17D—H17F | 0.9600 | C21Z—C23Z | 1.52 (2) |
C18D—C19D | 1.48 (2) | C22Z—H22I | 0.9600 |
C18D—C20D | 1.49 (2) | C22Z—H22J | 0.9600 |
C18D—H18D | 0.9800 | C22Z—H22K | 0.9600 |
C19D—H19D | 0.9600 | C23Z—H23J | 0.9600 |
C19D—H19E | 0.9600 | C23Z—H23K | 0.9600 |
C19D—H19F | 0.9600 | C23Z—H23L | 0.9600 |
C20D—H20D | 0.9600 | N1—C25 | 1.511 (9) |
C20D—H20E | 0.9600 | N1—H1A | 0.8900 |
C20D—H20F | 0.9600 | N1—H1B | 0.8900 |
C21D—C23D | 1.49 (2) | N1—H1C | 0.8900 |
C21D—C22D | 1.54 (2) | C24—C25 | 1.522 (11) |
C21D—H21D | 0.9800 | C24—H24A | 0.9600 |
C22D—H22D | 0.9700 | C24—H24B | 0.9600 |
C22D—H22E | 0.9700 | C24—H24C | 0.9600 |
C23D—H23D | 0.9600 | C25—C26 | 1.494 (12) |
C23D—H23E | 0.9600 | C25—H25 | 0.9800 |
C23D—H23F | 0.9600 | C26—C31 | 1.361 (15) |
O1P—C7P | 1.40 (2) | C26—C27 | 1.384 (15) |
O2P—C14P | 1.259 (9) | C27—C28 | 1.403 (16) |
O3P—C14P | 1.233 (10) | C27—H27 | 0.9300 |
C1P—C6P | 1.39 (2) | C28—C29 | 1.35 (2) |
C1P—C2P | 1.40 (2) | C28—H28 | 0.9300 |
C1P—C7P | 1.51 (2) | C29—C30 | 1.38 (2) |
C2P—C3P | 1.40 (2) | C29—H29 | 0.9300 |
C2P—C15P | 1.50 (2) | C30—C31 | 1.385 (17) |
C3P—C4P | 1.38 (2) | C30—H30 | 0.9300 |
C3P—H3P | 0.9300 | C31—H31 | 0.9300 |
C4P—C5P | 1.38 (2) | ||
C2—C1—C6 | 118.1 (19) | C1P—C7P—C8P | 120 (2) |
C2—C1—C7 | 125 (2) | O1P—C7P—C15P | 115 (3) |
C6—C1—C7 | 117 (2) | C1P—C7P—C15P | 84.0 (16) |
C1—C2—C3 | 122 (2) | C8P—C7P—C15P | 108.1 (17) |
C1—C2—C15 | 119 (2) | C9P—C8P—C13P | 118 (2) |
C3—C2—C15 | 118 (2) | C9P—C8P—C7P | 121 (2) |
C4—C3—C2 | 120 (2) | C13P—C8P—C7P | 121 (2) |
C4—C3—H3 | 120.0 | C8P—C9P—C10P | 121 (3) |
C2—C3—H3 | 120.0 | C8P—C9P—H9P | 119.5 |
C5—C4—C3 | 117 (2) | C10P—C9P—H9P | 119.5 |
C5—C4—C18 | 123 (2) | C11P—C10P—C9P | 121 (3) |
C3—C4—C18 | 120 (2) | C11P—C10P—H10P | 119.4 |
C4—C5—C6 | 123 (2) | C9P—C10P—H10P | 119.4 |
C4—C5—H5 | 118.5 | C10P—C11P—C12P | 118 (2) |
C6—C5—H5 | 118.5 | C10P—C11P—C14P | 125 (2) |
C1—C6—C5 | 120 (2) | C12P—C11P—C14P | 117 (2) |
C1—C6—C21 | 119 (2) | C13P—C12P—C11P | 120 (3) |
C5—C6—C21 | 121 (2) | C13P—C12P—H12P | 120.2 |
O1—C7—C8 | 119 (2) | C11P—C12P—H12P | 120.2 |
O1—C7—C1 | 124 (3) | C8P—C13P—C12P | 122 (3) |
C8—C7—C1 | 117 (2) | C8P—C13P—H13P | 119.0 |
C13—C8—C9 | 122 (2) | C12P—C13P—H13P | 119.0 |
C13—C8—C7 | 121 (2) | O3P—C14P—O2P | 123.3 (8) |
C9—C8—C7 | 117 (2) | O3P—C14P—C11P | 120.7 (15) |
C8—C9—C10 | 116 (2) | O2P—C14P—C11P | 115.2 (15) |
C8—C9—H9 | 121.8 | C2P—C15P—C16P | 123 (3) |
C10—C9—H9 | 121.8 | C2P—C15P—C17P | 119 (3) |
C11—C10—C9 | 125 (2) | C16P—C15P—C17P | 105 (3) |
C11—C10—H10 | 117.7 | C2P—C15P—C7P | 85.8 (17) |
C9—C10—H10 | 117.7 | C16P—C15P—C7P | 109 (3) |
C10—C11—C12 | 117.3 (19) | C17P—C15P—C7P | 112 (3) |
C10—C11—C14 | 122 (2) | C15P—C16P—H16G | 109.5 |
C12—C11—C14 | 120 (2) | C15P—C16P—H16H | 109.5 |
C13—C12—C11 | 120 (2) | H16G—C16P—H16H | 109.5 |
C13—C12—H12 | 120.1 | C15P—C16P—H16I | 109.5 |
C11—C12—H12 | 120.1 | H16G—C16P—H16I | 109.5 |
C8—C13—C12 | 120 (2) | H16H—C16P—H16I | 109.5 |
C8—C13—H13 | 120.2 | C15P—C17P—H17G | 109.5 |
C12—C13—H13 | 120.2 | C15P—C17P—H17H | 109.5 |
O3—C14—O2 | 123.3 (8) | H17G—C17P—H17H | 109.5 |
O3—C14—C11 | 118.8 (14) | C15P—C17P—H17I | 109.5 |
O2—C14—C11 | 117.9 (14) | H17G—C17P—H17I | 109.5 |
C16—C15—C17 | 114 (3) | H17H—C17P—H17I | 109.5 |
C16—C15—C2 | 112 (3) | C20P—C18P—C4P | 103 (3) |
C17—C15—C2 | 112 (2) | C20P—C18P—C19P | 110 (3) |
C16—C15—H15 | 106.3 | C4P—C18P—C19P | 109 (3) |
C17—C15—H15 | 106.3 | C20P—C18P—H18P | 111.4 |
C2—C15—H15 | 106.3 | C4P—C18P—H18P | 111.4 |
C15—C16—H16A | 109.5 | C19P—C18P—H18P | 111.4 |
C15—C16—H16B | 109.5 | C18P—C19P—H19G | 109.5 |
H16A—C16—H16B | 109.5 | C18P—C19P—H19H | 109.5 |
C15—C16—H16C | 109.5 | H19G—C19P—H19H | 109.5 |
H16A—C16—H16C | 109.5 | C18P—C19P—H19I | 109.5 |
H16B—C16—H16C | 109.5 | H19G—C19P—H19I | 109.5 |
C15—C17—H17A | 109.5 | H19H—C19P—H19I | 109.5 |
C15—C17—H17B | 109.5 | C18P—C20P—H20G | 109.5 |
H17A—C17—H17B | 109.5 | C18P—C20P—H20H | 109.5 |
C15—C17—H17C | 109.5 | H20G—C20P—H20H | 109.5 |
H17A—C17—H17C | 109.5 | C18P—C20P—H20I | 109.5 |
H17B—C17—H17C | 109.5 | H20G—C20P—H20I | 109.5 |
C20—C18—C19 | 111 (3) | H20H—C20P—H20I | 109.5 |
C20—C18—C4 | 111 (2) | C6P—C21P—C23P | 115 (3) |
C19—C18—C4 | 113 (2) | C6P—C21P—C22P | 112 (3) |
C20—C18—H18 | 107.1 | C23P—C21P—C22P | 106 (3) |
C19—C18—H18 | 107.1 | C6P—C21P—H21P | 108.1 |
C4—C18—H18 | 107.1 | C23P—C21P—H21P | 108.1 |
C18—C19—H19A | 109.5 | C22P—C21P—H21P | 108.1 |
C18—C19—H19B | 109.5 | C21P—C22P—H22F | 109.5 |
H19A—C19—H19B | 109.5 | C21P—C22P—H22G | 109.5 |
C18—C19—H19C | 109.5 | H22F—C22P—H22G | 109.5 |
H19A—C19—H19C | 109.5 | C21P—C22P—H22H | 109.5 |
H19B—C19—H19C | 109.5 | H22F—C22P—H22H | 109.5 |
C18—C20—H20A | 109.5 | H22G—C22P—H22H | 109.5 |
C18—C20—H20B | 109.5 | C21P—C23P—H23G | 109.5 |
H20A—C20—H20B | 109.5 | C21P—C23P—H23H | 109.5 |
C18—C20—H20C | 109.5 | H23G—C23P—H23H | 109.5 |
H20A—C20—H20C | 109.5 | C21P—C23P—H23I | 109.5 |
H20B—C20—H20C | 109.5 | H23G—C23P—H23I | 109.5 |
C22—C21—C6 | 110 (2) | H23H—C23P—H23I | 109.5 |
C22—C21—C23 | 110 (2) | C5Z—C6Z—C1Z | 120.0 |
C6—C21—C23 | 108 (2) | C5Z—C6Z—C21Z | 146.2 (18) |
C22—C21—H21 | 109.7 | C1Z—C6Z—C21Z | 93.4 (18) |
C6—C21—H21 | 109.7 | C2Z—C1Z—C6Z | 119.8 |
C23—C21—H21 | 109.7 | C2Z—C1Z—C7Z | 143.0 (18) |
C21—C22—H22A | 109.5 | C6Z—C1Z—C7Z | 96.1 (18) |
C21—C22—H22B | 109.5 | C1Z—C2Z—C3Z | 120.22 (8) |
H22A—C22—H22B | 109.5 | C1Z—C2Z—C15Z | 117 (2) |
C21—C22—H22C | 109.5 | C3Z—C2Z—C15Z | 123 (2) |
H22A—C22—H22C | 109.5 | C4Z—C3Z—C2Z | 120.0 |
H22B—C22—H22C | 109.5 | C4Z—C3Z—H3Z | 120.0 |
C21—C23—H23A | 109.5 | C2Z—C3Z—H3Z | 120.1 |
C21—C23—H23B | 109.5 | C3Z—C4Z—C5Z | 120.0 |
H23A—C23—H23B | 109.5 | C3Z—C4Z—C18Z | 117 (2) |
C21—C23—H23C | 109.5 | C5Z—C4Z—C18Z | 123 (2) |
H23A—C23—H23C | 109.5 | C4Z—C5Z—C6Z | 120.07 (8) |
H23B—C23—H23C | 109.5 | C4Z—C5Z—H5Z | 119.9 |
C2D—C1D—C6D | 122.1 (19) | C6Z—C5Z—H5Z | 120.0 |
C2D—C1D—C7D | 125 (2) | O1Z—C7Z—C1Z | 94 (3) |
C6D—C1D—C7D | 113.2 (17) | O1Z—C7Z—C8Z | 114 (3) |
C1D—C2D—C3D | 118 (2) | C1Z—C7Z—C8Z | 119 (3) |
C1D—C2D—C15D | 123 (2) | O1Z—C7Z—C21Z | 116 (3) |
C3D—C2D—C15D | 118 (2) | C1Z—C7Z—C21Z | 83.9 (17) |
C2D—C3D—C4D | 122 (2) | C8Z—C7Z—C21Z | 123 (3) |
C2D—C3D—H3D | 119.2 | C13Z—C8Z—C9Z | 120.1 |
C4D—C3D—H3D | 119.2 | C13Z—C8Z—C7Z | 119 (2) |
C5D—C4D—C3D | 118 (2) | C9Z—C8Z—C7Z | 121 (2) |
C5D—C4D—C18D | 115 (2) | C10Z—C9Z—C8Z | 120.0 |
C3D—C4D—C18D | 127 (2) | C10Z—C9Z—H9Z | 119.8 |
C6D—C5D—C4D | 120 (2) | C8Z—C9Z—H9Z | 120.2 |
C6D—C5D—H5D | 120.2 | C9Z—C10Z—C11Z | 119.8 |
C4D—C5D—H5D | 120.2 | C9Z—C10Z—H10Z | 120.3 |
C1D—C6D—C5D | 120 (2) | C11Z—C10Z—H10Z | 119.8 |
C1D—C6D—C21D | 107.7 (17) | C12Z—C11Z—C10Z | 120.4 |
C5D—C6D—C21D | 132 (2) | C12Z—C11Z—C14Z | 117 (2) |
O1D—C7D—C22D | 110 (2) | C10Z—C11Z—C14Z | 123 (2) |
O1D—C7D—C8D | 110 (2) | C11Z—C12Z—C13Z | 119.7 |
C22D—C7D—C8D | 116 (2) | C11Z—C12Z—H12Z | 120.5 |
O1D—C7D—C1D | 111 (2) | C13Z—C12Z—H12Z | 119.7 |
C22D—C7D—C1D | 99.5 (16) | C8Z—C13Z—C12Z | 119.9 |
C8D—C7D—C1D | 111 (2) | C8Z—C13Z—H13Z | 120.1 |
C13D—C8D—C9D | 119 (2) | C12Z—C13Z—H13Z | 120.0 |
C13D—C8D—C7D | 124 (2) | O3Z—C14Z—O2Z | 123.3 (8) |
C9D—C8D—C7D | 117 (2) | O3Z—C14Z—C11Z | 120.2 (16) |
C10D—C9D—C8D | 119 (2) | O2Z—C14Z—C11Z | 116.5 (16) |
C10D—C9D—H9D | 120.5 | C17Z—C15Z—C16Z | 121 (4) |
C8D—C9D—H9D | 120.5 | C17Z—C15Z—C2Z | 112 (3) |
C9D—C10D—C11D | 124 (2) | C16Z—C15Z—C2Z | 108 (3) |
C9D—C10D—H10D | 118.2 | C17Z—C15Z—H15Z | 105.0 |
C11D—C10D—H10D | 118.2 | C16Z—C15Z—H15Z | 105.0 |
C10D—C11D—C12D | 116 (2) | C2Z—C15Z—H15Z | 105.0 |
C10D—C11D—C14D | 122 (2) | C15Z—C16Z—H16J | 109.5 |
C12D—C11D—C14D | 122 (2) | C15Z—C16Z—H16K | 109.5 |
C13D—C12D—C11D | 121 (3) | H16J—C16Z—H16K | 109.5 |
C13D—C12D—H12D | 119.4 | C15Z—C16Z—H16L | 109.5 |
C11D—C12D—H12D | 119.4 | H16J—C16Z—H16L | 109.5 |
C8D—C13D—C12D | 121 (3) | H16K—C16Z—H16L | 109.5 |
C8D—C13D—H13D | 119.4 | C15Z—C17Z—H17J | 109.5 |
C12D—C13D—H13D | 119.4 | C15Z—C17Z—H17K | 109.5 |
O3D—C14D—O2D | 123.3 (8) | H17J—C17Z—H17K | 109.5 |
O3D—C14D—C11D | 115.1 (14) | C15Z—C17Z—H17L | 109.5 |
O2D—C14D—C11D | 121.2 (14) | H17J—C17Z—H17L | 109.5 |
C16D—C15D—C2D | 111 (2) | H17K—C17Z—H17L | 109.5 |
C16D—C15D—C17D | 111 (2) | C4Z—C18Z—C19Z | 100 (3) |
C2D—C15D—C17D | 109 (2) | C4Z—C18Z—C20Z | 116 (3) |
C16D—C15D—H15D | 108.9 | C19Z—C18Z—C20Z | 109 (4) |
C2D—C15D—H15D | 108.9 | C4Z—C18Z—H18Z | 110.3 |
C17D—C15D—H15D | 108.9 | C19Z—C18Z—H18Z | 110.3 |
C15D—C16D—H16D | 109.5 | C20Z—C18Z—H18Z | 110.3 |
C15D—C16D—H16E | 109.5 | C18Z—C19Z—H19J | 109.5 |
H16D—C16D—H16E | 109.5 | C18Z—C19Z—H19K | 109.5 |
C15D—C16D—H16F | 109.5 | H19J—C19Z—H19K | 109.5 |
H16D—C16D—H16F | 109.5 | C18Z—C19Z—H19L | 109.5 |
H16E—C16D—H16F | 109.5 | H19J—C19Z—H19L | 109.5 |
C15D—C17D—H17D | 109.5 | H19K—C19Z—H19L | 109.5 |
C15D—C17D—H17E | 109.5 | C18Z—C20Z—H20J | 109.5 |
H17D—C17D—H17E | 109.5 | C18Z—C20Z—H20K | 109.5 |
C15D—C17D—H17F | 109.5 | H20J—C20Z—H20K | 109.5 |
H17D—C17D—H17F | 109.5 | C18Z—C20Z—H20L | 109.5 |
H17E—C17D—H17F | 109.5 | H20J—C20Z—H20L | 109.5 |
C19D—C18D—C20D | 120 (3) | H20K—C20Z—H20L | 109.5 |
C19D—C18D—C4D | 123 (2) | C6Z—C21Z—C22Z | 109 (3) |
C20D—C18D—C4D | 116 (2) | C6Z—C21Z—C23Z | 120 (3) |
C19D—C18D—H18D | 92.8 | C22Z—C21Z—C23Z | 112 (3) |
C20D—C18D—H18D | 92.8 | C6Z—C21Z—C7Z | 86.4 (17) |
C4D—C18D—H18D | 92.8 | C22Z—C21Z—C7Z | 112 (3) |
C18D—C19D—H19D | 109.5 | C23Z—C21Z—C7Z | 114 (3) |
C18D—C19D—H19E | 109.5 | C21Z—C22Z—H22I | 109.5 |
H19D—C19D—H19E | 109.5 | C21Z—C22Z—H22J | 109.5 |
C18D—C19D—H19F | 109.5 | H22I—C22Z—H22J | 109.5 |
H19D—C19D—H19F | 109.5 | C21Z—C22Z—H22K | 109.5 |
H19E—C19D—H19F | 109.5 | H22I—C22Z—H22K | 109.5 |
C18D—C20D—H20D | 109.5 | H22J—C22Z—H22K | 109.5 |
C18D—C20D—H20E | 109.5 | C21Z—C23Z—H23J | 109.5 |
H20D—C20D—H20E | 109.5 | C21Z—C23Z—H23K | 109.5 |
C18D—C20D—H20F | 109.5 | H23J—C23Z—H23K | 109.5 |
H20D—C20D—H20F | 109.5 | C21Z—C23Z—H23L | 109.5 |
H20E—C20D—H20F | 109.5 | H23J—C23Z—H23L | 109.5 |
C23D—C21D—C6D | 117 (3) | H23K—C23Z—H23L | 109.5 |
C23D—C21D—C22D | 115 (3) | C25—N1—H1A | 109.5 |
C6D—C21D—C22D | 102.2 (19) | C25—N1—H1B | 109.5 |
C23D—C21D—H21D | 107.1 | H1A—N1—H1B | 109.5 |
C6D—C21D—H21D | 107.1 | C25—N1—H1C | 109.5 |
C22D—C21D—H21D | 107.1 | H1A—N1—H1C | 109.5 |
C7D—C22D—C21D | 107.9 (17) | H1B—N1—H1C | 109.5 |
C7D—C22D—H22D | 110.1 | C25—C24—H24A | 109.5 |
C21D—C22D—H22D | 110.1 | C25—C24—H24B | 109.5 |
C7D—C22D—H22E | 110.1 | H24A—C24—H24B | 109.5 |
C21D—C22D—H22E | 110.1 | C25—C24—H24C | 109.5 |
H22D—C22D—H22E | 108.4 | H24A—C24—H24C | 109.5 |
C21D—C23D—H23D | 109.5 | H24B—C24—H24C | 109.5 |
C21D—C23D—H23E | 109.5 | C26—C25—N1 | 109.1 (7) |
H23D—C23D—H23E | 109.5 | C26—C25—C24 | 115.0 (9) |
C21D—C23D—H23F | 109.5 | N1—C25—C24 | 109.0 (7) |
H23D—C23D—H23F | 109.5 | C26—C25—H25 | 107.8 |
H23E—C23D—H23F | 109.5 | N1—C25—H25 | 107.8 |
C6P—C1P—C2P | 122 (2) | C24—C25—H25 | 107.8 |
C6P—C1P—C7P | 142 (2) | C31—C26—C27 | 119.2 (12) |
C2P—C1P—C7P | 95.6 (19) | C31—C26—C25 | 121.5 (13) |
C3P—C2P—C1P | 119 (2) | C27—C26—C25 | 119.3 (13) |
C3P—C2P—C15P | 147 (3) | C26—C27—C28 | 119.8 (14) |
C1P—C2P—C15P | 93.9 (19) | C26—C27—H27 | 120.1 |
C4P—C3P—C2P | 117 (3) | C28—C27—H27 | 120.1 |
C4P—C3P—H3P | 121.3 | C29—C28—C27 | 120 (2) |
C2P—C3P—H3P | 121.3 | C29—C28—H28 | 120.1 |
C5P—C4P—C3P | 125 (3) | C27—C28—H28 | 120.1 |
C5P—C4P—C18P | 115 (3) | C28—C29—C30 | 121 (2) |
C3P—C4P—C18P | 120 (3) | C28—C29—H29 | 119.6 |
C4P—C5P—C6P | 118 (3) | C30—C29—H29 | 119.6 |
C4P—C5P—H5P | 121.0 | C29—C30—C31 | 119 (2) |
C6P—C5P—H5P | 121.0 | C29—C30—H30 | 120.5 |
C1P—C6P—C5P | 119 (2) | C31—C30—H30 | 120.5 |
C1P—C6P—C21P | 127 (3) | C26—C31—C30 | 121.3 (16) |
C5P—C6P—C21P | 114 (2) | C26—C31—H31 | 119.3 |
O1P—C7P—C1P | 123 (3) | C30—C31—H31 | 119.3 |
O1P—C7P—C8P | 105 (2) |
C31H39NO3 | Dx = 1.118 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 1976 reflections |
a = 6.3861 (5) Å | θ = 1.6–18.8° |
b = 13.4799 (10) Å | µ = 0.07 mm−1 |
c = 32.6933 (17) Å | T = 299 K |
V = 2814.4 (3) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.12 × 0.10 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 5437 independent reflections |
Radiation source: fine-focus sealed tube | 1797 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.143 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −14→16 |
Tmin = 0.861, Tmax = 1.000 | l = −40→40 |
25037 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.090 | H-atom parameters constrained |
wR(F2) = 0.210 | w = 1/[σ2(Fo2) + (0.0377P)2 + 0.5056P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
5437 reflections | Δρmax = 0.14 e Å−3 |
426 parameters | Δρmin = −0.16 e Å−3 |
511 restraints | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −1.2 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 1.046 (5) | 0.242 (2) | 0.6362 (13) | 0.083 (8) | 0.305 (4) |
O2 | 0.6554 (10) | 0.6319 (4) | 0.51810 (16) | 0.0869 (19) | 0.305 (4) |
O3 | 0.3544 (11) | 0.6162 (5) | 0.54967 (17) | 0.099 (2) | 0.305 (4) |
C6 | 0.696 (5) | 0.1990 (19) | 0.6995 (6) | 0.064 (10)* | 0.305 (4) |
C1 | 0.822 (6) | 0.282 (2) | 0.6932 (6) | 0.064 (11)* | 0.305 (4) |
C2 | 0.881 (6) | 0.343 (2) | 0.7257 (8) | 0.070 (11)* | 0.305 (4) |
C3 | 0.811 (6) | 0.318 (2) | 0.7649 (6) | 0.078 (10)* | 0.305 (4) |
H3 | 0.8480 | 0.3589 | 0.7867 | 0.094* | 0.305 (4) |
C4 | 0.688 (5) | 0.236 (2) | 0.7722 (5) | 0.053 (8)* | 0.305 (4) |
C5 | 0.631 (5) | 0.1784 (17) | 0.7391 (6) | 0.067 (10)* | 0.305 (4) |
H5 | 0.5456 | 0.1235 | 0.7435 | 0.080* | 0.305 (4) |
C7 | 0.904 (4) | 0.2922 (19) | 0.6498 (7) | 0.091 (11)* | 0.305 (4) |
C8 | 0.804 (4) | 0.3673 (19) | 0.6227 (8) | 0.063 (11)* | 0.305 (4) |
C9 | 0.924 (3) | 0.4103 (15) | 0.5924 (7) | 0.048 (7)* | 0.305 (4) |
H9 | 1.0615 | 0.3896 | 0.5885 | 0.057* | 0.305 (4) |
C10 | 0.842 (4) | 0.4835 (13) | 0.5680 (5) | 0.058 (8)* | 0.305 (4) |
H10 | 0.9258 | 0.5125 | 0.5480 | 0.069* | 0.305 (4) |
C11 | 0.637 (4) | 0.5145 (10) | 0.5726 (5) | 0.062 (11)* | 0.305 (4) |
C12 | 0.515 (4) | 0.469 (2) | 0.6016 (9) | 0.067 (11)* | 0.305 (4) |
H12 | 0.3749 | 0.4870 | 0.6043 | 0.081* | 0.305 (4) |
C13 | 0.598 (4) | 0.397 (3) | 0.6268 (10) | 0.066 (11)* | 0.305 (4) |
H13 | 0.5145 | 0.3677 | 0.6468 | 0.079* | 0.305 (4) |
C14 | 0.5391 (16) | 0.5922 (6) | 0.5448 (2) | 0.071 (2) | 0.305 (4) |
C15 | 1.007 (5) | 0.435 (2) | 0.7160 (12) | 0.066 (10)* | 0.305 (4) |
H15 | 1.0047 | 0.4381 | 0.6860 | 0.079* | 0.305 (4) |
C16 | 1.234 (5) | 0.430 (4) | 0.726 (2) | 0.071 (15)* | 0.305 (4) |
H16A | 1.2901 | 0.3680 | 0.7167 | 0.107* | 0.305 (4) |
H16B | 1.3059 | 0.4836 | 0.7122 | 0.107* | 0.305 (4) |
H16C | 1.2530 | 0.4364 | 0.7548 | 0.107* | 0.305 (4) |
C17 | 0.902 (7) | 0.530 (2) | 0.7287 (13) | 0.084 (13)* | 0.305 (4) |
H17A | 0.7561 | 0.5268 | 0.7213 | 0.126* | 0.305 (4) |
H17B | 0.9139 | 0.5375 | 0.7578 | 0.126* | 0.305 (4) |
H17C | 0.9668 | 0.5847 | 0.7152 | 0.126* | 0.305 (4) |
C18 | 0.628 (5) | 0.209 (3) | 0.8176 (7) | 0.073 (10)* | 0.305 (4) |
H18 | 0.6462 | 0.1369 | 0.8203 | 0.087* | 0.305 (4) |
C19 | 0.771 (7) | 0.257 (4) | 0.8490 (10) | 0.066 (11)* | 0.305 (4) |
H19A | 0.9139 | 0.2426 | 0.8424 | 0.098* | 0.305 (4) |
H19B | 0.7498 | 0.3278 | 0.8486 | 0.098* | 0.305 (4) |
H19C | 0.7387 | 0.2321 | 0.8757 | 0.098* | 0.305 (4) |
C20 | 0.407 (6) | 0.230 (4) | 0.8269 (17) | 0.124 (19)* | 0.305 (4) |
H20A | 0.3188 | 0.1989 | 0.8069 | 0.186* | 0.305 (4) |
H20B | 0.3730 | 0.2047 | 0.8536 | 0.186* | 0.305 (4) |
H20C | 0.3841 | 0.3004 | 0.8264 | 0.186* | 0.305 (4) |
C21 | 0.647 (5) | 0.130 (2) | 0.6643 (9) | 0.073 (10)* | 0.305 (4) |
H21 | 0.6336 | 0.1673 | 0.6388 | 0.087* | 0.305 (4) |
C22 | 0.815 (6) | 0.051 (2) | 0.6599 (12) | 0.095 (13)* | 0.305 (4) |
H22A | 0.7804 | 0.0077 | 0.6374 | 0.142* | 0.305 (4) |
H22B | 0.9478 | 0.0816 | 0.6548 | 0.142* | 0.305 (4) |
H22C | 0.8228 | 0.0122 | 0.6846 | 0.142* | 0.305 (4) |
C23 | 0.435 (5) | 0.076 (3) | 0.6748 (13) | 0.084 (11)* | 0.305 (4) |
H23A | 0.3994 | 0.0314 | 0.6531 | 0.126* | 0.305 (4) |
H23B | 0.4504 | 0.0399 | 0.6999 | 0.126* | 0.305 (4) |
H23C | 0.3266 | 0.1249 | 0.6778 | 0.126* | 0.305 (4) |
O1D | 1.098 (4) | 0.271 (2) | 0.6404 (11) | 0.074 (9) | 0.356 (4) |
O2D | 0.6554 (10) | 0.6319 (4) | 0.51810 (16) | 0.0869 (19) | 0.356 (4) |
O3D | 0.3544 (11) | 0.6162 (5) | 0.54967 (17) | 0.099 (2) | 0.356 (4) |
C1D | 0.810 (5) | 0.280 (2) | 0.6910 (6) | 0.067 (10)* | 0.356 (4) |
C2D | 0.885 (5) | 0.3469 (19) | 0.7181 (7) | 0.061 (8)* | 0.356 (4) |
C3D | 0.839 (5) | 0.337 (2) | 0.7596 (7) | 0.066 (8)* | 0.356 (4) |
H3D | 0.9015 | 0.3793 | 0.7784 | 0.079* | 0.356 (4) |
C4D | 0.698 (5) | 0.263 (2) | 0.7734 (7) | 0.075 (9)* | 0.356 (4) |
C5D | 0.612 (6) | 0.200 (2) | 0.7439 (7) | 0.069 (9)* | 0.356 (4) |
H5D | 0.5180 | 0.1510 | 0.7520 | 0.083* | 0.356 (4) |
C6D | 0.665 (6) | 0.208 (2) | 0.7028 (7) | 0.067 (10)* | 0.356 (4) |
C7D | 0.871 (4) | 0.2723 (16) | 0.6448 (6) | 0.077 (8)* | 0.356 (4) |
C9D | 0.886 (5) | 0.386 (2) | 0.5836 (8) | 0.071 (8)* | 0.356 (4) |
H9D | 1.0109 | 0.3556 | 0.5759 | 0.085* | 0.356 (4) |
C8D | 0.782 (4) | 0.3576 (18) | 0.6189 (8) | 0.060 (9)* | 0.356 (4) |
C13D | 0.600 (5) | 0.403 (3) | 0.6287 (11) | 0.063 (10)* | 0.356 (4) |
H13D | 0.5311 | 0.3837 | 0.6525 | 0.076* | 0.356 (4) |
C12D | 0.511 (4) | 0.477 (3) | 0.6055 (10) | 0.066 (10)* | 0.356 (4) |
H12D | 0.3851 | 0.5060 | 0.6133 | 0.079* | 0.356 (4) |
C11D | 0.614 (4) | 0.5079 (14) | 0.5694 (7) | 0.057 (9)* | 0.356 (4) |
C10D | 0.799 (4) | 0.460 (2) | 0.5602 (7) | 0.055 (7)* | 0.356 (4) |
H10D | 0.8692 | 0.4793 | 0.5366 | 0.066* | 0.356 (4) |
C14D | 0.5391 (16) | 0.5922 (6) | 0.5448 (2) | 0.071 (2) | 0.356 (4) |
C15D | 1.043 (4) | 0.4270 (19) | 0.7059 (10) | 0.077 (9)* | 0.356 (4) |
H15D | 1.0703 | 0.4216 | 0.6764 | 0.093* | 0.356 (4) |
C16D | 1.241 (5) | 0.407 (3) | 0.7282 (16) | 0.094 (15)* | 0.356 (4) |
H16D | 1.3431 | 0.4562 | 0.7211 | 0.141* | 0.356 (4) |
H16E | 1.2151 | 0.4091 | 0.7571 | 0.141* | 0.356 (4) |
H16F | 1.2923 | 0.3424 | 0.7209 | 0.141* | 0.356 (4) |
C17D | 0.941 (7) | 0.528 (2) | 0.7144 (15) | 0.087 (13)* | 0.356 (4) |
H17D | 0.8144 | 0.5339 | 0.6986 | 0.131* | 0.356 (4) |
H17E | 0.9075 | 0.5331 | 0.7430 | 0.131* | 0.356 (4) |
H17F | 1.0355 | 0.5802 | 0.7069 | 0.131* | 0.356 (4) |
C18D | 0.626 (5) | 0.240 (3) | 0.8175 (7) | 0.101 (11)* | 0.356 (4) |
H18D | 0.6017 | 0.1698 | 0.8117 | 0.121* | 0.356 (4) |
C19D | 0.777 (6) | 0.219 (2) | 0.8508 (8) | 0.095 (13)* | 0.356 (4) |
H19D | 0.9135 | 0.2085 | 0.8394 | 0.142* | 0.356 (4) |
H19E | 0.7811 | 0.2740 | 0.8694 | 0.142* | 0.356 (4) |
H19F | 0.7337 | 0.1604 | 0.8653 | 0.142* | 0.356 (4) |
C20D | 0.404 (5) | 0.259 (4) | 0.8272 (13) | 0.087 (13)* | 0.356 (4) |
H20D | 0.3276 | 0.2713 | 0.8024 | 0.131* | 0.356 (4) |
H20E | 0.3455 | 0.2020 | 0.8407 | 0.131* | 0.356 (4) |
H20F | 0.3929 | 0.3156 | 0.8449 | 0.131* | 0.356 (4) |
C21D | 0.599 (5) | 0.151 (2) | 0.6647 (9) | 0.083 (10)* | 0.356 (4) |
H21D | 0.4774 | 0.1854 | 0.6532 | 0.099* | 0.356 (4) |
C22D | 0.786 (4) | 0.1709 (15) | 0.6356 (7) | 0.089 (8)* | 0.356 (4) |
H22D | 0.8941 | 0.1213 | 0.6397 | 0.107* | 0.356 (4) |
H22E | 0.7402 | 0.1676 | 0.6074 | 0.107* | 0.356 (4) |
C23D | 0.538 (6) | 0.0449 (19) | 0.6698 (10) | 0.122 (13)* | 0.356 (4) |
H23D | 0.4995 | 0.0176 | 0.6437 | 0.184* | 0.356 (4) |
H23E | 0.6532 | 0.0082 | 0.6809 | 0.184* | 0.356 (4) |
H23F | 0.4203 | 0.0405 | 0.6881 | 0.184* | 0.356 (4) |
O1P | 1.111 (7) | 0.304 (3) | 0.6505 (16) | 0.076 (9) | 0.193 (4) |
O2P | 0.6554 (10) | 0.6319 (4) | 0.51810 (16) | 0.0869 (19) | 0.193 (4) |
O3P | 0.3544 (11) | 0.6162 (5) | 0.54967 (17) | 0.099 (2) | 0.193 (4) |
C6P | 0.662 (6) | 0.212 (2) | 0.7040 (9) | 0.065 (13)* | 0.193 (4) |
C1P | 0.799 (6) | 0.291 (2) | 0.6993 (8) | 0.058 (12)* | 0.193 (4) |
C2P | 0.853 (7) | 0.349 (3) | 0.7329 (9) | 0.072 (12)* | 0.193 (4) |
C3P | 0.769 (6) | 0.328 (3) | 0.7712 (8) | 0.064 (11)* | 0.193 (4) |
H3P | 0.8065 | 0.3674 | 0.7941 | 0.077* | 0.193 (4) |
C4P | 0.634 (6) | 0.248 (3) | 0.7759 (8) | 0.080 (12)* | 0.193 (4) |
C5P | 0.579 (6) | 0.190 (3) | 0.7424 (10) | 0.068 (13)* | 0.193 (4) |
H5P | 0.4859 | 0.1362 | 0.7456 | 0.082* | 0.193 (4) |
C7P | 0.938 (4) | 0.3479 (19) | 0.6698 (7) | 0.068 (10)* | 0.193 (4) |
C8P | 0.831 (4) | 0.4092 (15) | 0.6363 (6) | 0.047 (9)* | 0.193 (4) |
C9P | 0.954 (3) | 0.451 (2) | 0.6056 (8) | 0.070 (11)* | 0.193 (4) |
H9P | 1.1002 | 0.4381 | 0.6051 | 0.083* | 0.193 (4) |
C10P | 0.863 (4) | 0.5099 (19) | 0.5758 (7) | 0.068 (11)* | 0.193 (4) |
H10P | 0.9472 | 0.5381 | 0.5549 | 0.082* | 0.193 (4) |
C11P | 0.649 (5) | 0.5281 (15) | 0.5766 (7) | 0.066 (12)* | 0.193 (4) |
C12P | 0.525 (4) | 0.487 (3) | 0.6071 (10) | 0.063 (13)* | 0.193 (4) |
H12P | 0.3790 | 0.4991 | 0.6077 | 0.076* | 0.193 (4) |
C13P | 0.616 (4) | 0.427 (3) | 0.6370 (8) | 0.062 (12)* | 0.193 (4) |
H13P | 0.5320 | 0.3991 | 0.6579 | 0.075* | 0.193 (4) |
C14P | 0.5391 (16) | 0.5922 (6) | 0.5448 (2) | 0.071 (2) | 0.193 (4) |
C15P | 0.987 (6) | 0.421 (2) | 0.7095 (10) | 0.071 (13)* | 0.193 (4) |
C16P | 1.221 (7) | 0.433 (6) | 0.715 (2) | 0.12 (2)* | 0.193 (4) |
H16G | 1.2710 | 0.4828 | 0.6964 | 0.177* | 0.193 (4) |
H16H | 1.2510 | 0.4515 | 0.7424 | 0.177* | 0.193 (4) |
H16I | 1.2886 | 0.3707 | 0.7087 | 0.177* | 0.193 (4) |
C17P | 0.894 (11) | 0.526 (3) | 0.706 (2) | 0.085 (19)* | 0.193 (4) |
H17G | 0.9887 | 0.5670 | 0.6903 | 0.128* | 0.193 (4) |
H17H | 0.7623 | 0.5221 | 0.6915 | 0.128* | 0.193 (4) |
H17I | 0.8737 | 0.5534 | 0.7323 | 0.128* | 0.193 (4) |
C18P | 0.559 (7) | 0.215 (4) | 0.8177 (10) | 0.087 (13)* | 0.193 (4) |
H18P | 0.5577 | 0.1422 | 0.8197 | 0.105* | 0.193 (4) |
C19P | 0.686 (8) | 0.260 (6) | 0.8520 (14) | 0.11 (2)* | 0.193 (4) |
H19G | 0.6341 | 0.2373 | 0.8778 | 0.158* | 0.193 (4) |
H19H | 0.8303 | 0.2415 | 0.8491 | 0.158* | 0.193 (4) |
H19I | 0.6747 | 0.3314 | 0.8508 | 0.158* | 0.193 (4) |
C20P | 0.336 (6) | 0.256 (5) | 0.8166 (16) | 0.082 (17)* | 0.193 (4) |
H20G | 0.2596 | 0.2261 | 0.7946 | 0.124* | 0.193 (4) |
H20H | 0.2669 | 0.2426 | 0.8420 | 0.124* | 0.193 (4) |
H20I | 0.3412 | 0.3269 | 0.8124 | 0.124* | 0.193 (4) |
C21P | 0.578 (7) | 0.147 (3) | 0.6699 (13) | 0.071 (13)* | 0.193 (4) |
H21P | 0.5511 | 0.1894 | 0.6460 | 0.086* | 0.193 (4) |
C22P | 0.735 (8) | 0.067 (4) | 0.6576 (17) | 0.079 (15)* | 0.193 (4) |
H22F | 0.6775 | 0.0270 | 0.6360 | 0.119* | 0.193 (4) |
H22G | 0.8626 | 0.0972 | 0.6484 | 0.119* | 0.193 (4) |
H22H | 0.7649 | 0.0252 | 0.6808 | 0.119* | 0.193 (4) |
C23P | 0.373 (8) | 0.093 (5) | 0.681 (2) | 0.13 (2)* | 0.193 (4) |
H23G | 0.3283 | 0.0539 | 0.6582 | 0.194* | 0.193 (4) |
H23H | 0.3968 | 0.0514 | 0.7043 | 0.194* | 0.193 (4) |
H23I | 0.2672 | 0.1414 | 0.6875 | 0.194* | 0.193 (4) |
O1Z | 1.108 (6) | 0.283 (5) | 0.6555 (17) | 0.077 (10)* | 0.146 (4) |
O2Z | 0.6554 (10) | 0.6319 (4) | 0.51810 (16) | 0.0869 (19) | 0.146 (4) |
O3Z | 0.3544 (11) | 0.6162 (5) | 0.54967 (17) | 0.099 (2) | 0.146 (4) |
C6Z | 0.749 (7) | 0.220 (2) | 0.7082 (8) | 0.049 (11)* | 0.146 (4) |
C1Z | 0.866 (6) | 0.306 (2) | 0.7023 (8) | 0.056 (12)* | 0.146 (4) |
C2Z | 0.896 (7) | 0.371 (2) | 0.7346 (9) | 0.071 (13)* | 0.146 (4) |
C3Z | 0.811 (7) | 0.351 (3) | 0.7728 (8) | 0.081 (14)* | 0.146 (4) |
H3Z | 0.8322 | 0.3953 | 0.7949 | 0.097* | 0.146 (4) |
C4Z | 0.695 (6) | 0.265 (3) | 0.7787 (8) | 0.074 (14)* | 0.146 (4) |
C5Z | 0.664 (7) | 0.199 (3) | 0.7464 (9) | 0.067 (13)* | 0.146 (4) |
H5Z | 0.5845 | 0.1405 | 0.7504 | 0.080* | 0.146 (4) |
C7Z | 0.887 (6) | 0.292 (2) | 0.6565 (9) | 0.092 (14)* | 0.146 (4) |
C8Z | 0.800 (7) | 0.372 (3) | 0.6273 (11) | 0.057 (13)* | 0.146 (4) |
C9Z | 0.892 (9) | 0.385 (4) | 0.5890 (15) | 0.067 (14)* | 0.146 (4) |
H9Z | 1.0089 | 0.3456 | 0.5813 | 0.080* | 0.146 (4) |
C10Z | 0.812 (8) | 0.454 (4) | 0.5619 (12) | 0.060 (14)* | 0.146 (4) |
H10Z | 0.8737 | 0.4630 | 0.5357 | 0.072* | 0.146 (4) |
C11Z | 0.640 (5) | 0.5117 (15) | 0.5731 (9) | 0.061 (14)* | 0.146 (4) |
C12Z | 0.548 (6) | 0.500 (3) | 0.6113 (11) | 0.058 (13)* | 0.146 (4) |
H12Z | 0.4314 | 0.5389 | 0.6190 | 0.069* | 0.146 (4) |
C13Z | 0.628 (7) | 0.430 (3) | 0.6385 (10) | 0.065 (13)* | 0.146 (4) |
H13Z | 0.5665 | 0.4215 | 0.6646 | 0.078* | 0.146 (4) |
C14Z | 0.5391 (16) | 0.5922 (6) | 0.5448 (2) | 0.071 (2) | 0.146 (4) |
C15Z | 1.033 (8) | 0.460 (3) | 0.7279 (16) | 0.072 (13)* | 0.146 (4) |
H15Z | 1.0463 | 0.4671 | 0.6982 | 0.086* | 0.146 (4) |
C16Z | 1.243 (7) | 0.428 (5) | 0.743 (2) | 0.13 (3)* | 0.146 (4) |
H16J | 1.2788 | 0.3655 | 0.7313 | 0.194* | 0.146 (4) |
H16K | 1.3451 | 0.4771 | 0.7353 | 0.194* | 0.146 (4) |
H16L | 1.2391 | 0.4228 | 0.7723 | 0.194* | 0.146 (4) |
C17Z | 0.955 (11) | 0.555 (3) | 0.743 (2) | 0.12 (2)* | 0.146 (4) |
H17J | 0.8198 | 0.5683 | 0.7317 | 0.185* | 0.146 (4) |
H17K | 0.9446 | 0.5525 | 0.7725 | 0.185* | 0.146 (4) |
H17L | 1.0506 | 0.6068 | 0.7355 | 0.185* | 0.146 (4) |
C18Z | 0.610 (9) | 0.253 (4) | 0.8214 (11) | 0.098 (15)* | 0.146 (4) |
H18Z | 0.5902 | 0.1835 | 0.8293 | 0.118* | 0.146 (4) |
C19Z | 0.792 (10) | 0.303 (5) | 0.8442 (16) | 0.09 (2)* | 0.146 (4) |
H19J | 0.7642 | 0.3025 | 0.8731 | 0.141* | 0.146 (4) |
H19K | 0.9192 | 0.2673 | 0.8388 | 0.141* | 0.146 (4) |
H19L | 0.8065 | 0.3702 | 0.8350 | 0.141* | 0.146 (4) |
C20Z | 0.415 (9) | 0.317 (6) | 0.830 (2) | 0.12 (2)* | 0.146 (4) |
H20J | 0.3679 | 0.3062 | 0.8572 | 0.183* | 0.146 (4) |
H20K | 0.4489 | 0.3855 | 0.8259 | 0.183* | 0.146 (4) |
H20L | 0.3055 | 0.2983 | 0.8109 | 0.183* | 0.146 (4) |
C21Z | 0.766 (6) | 0.186 (2) | 0.6641 (10) | 0.086 (13)* | 0.146 (4) |
C22Z | 0.908 (8) | 0.096 (3) | 0.6633 (15) | 0.068 (16)* | 0.146 (4) |
H22I | 0.9218 | 0.0722 | 0.6357 | 0.103* | 0.146 (4) |
H22J | 1.0439 | 0.1137 | 0.6737 | 0.103* | 0.146 (4) |
H22K | 0.8498 | 0.0442 | 0.6801 | 0.103* | 0.146 (4) |
C23Z | 0.571 (9) | 0.171 (5) | 0.6382 (19) | 0.15 (3)* | 0.146 (4) |
H23J | 0.6103 | 0.1498 | 0.6114 | 0.220* | 0.146 (4) |
H23K | 0.4821 | 0.1224 | 0.6507 | 0.220* | 0.146 (4) |
H23L | 0.4963 | 0.2332 | 0.6363 | 0.220* | 0.146 (4) |
N1 | 0.0635 (10) | 0.6667 (4) | 0.49218 (17) | 0.072 (2) | |
H1A | 0.1650 | 0.6448 | 0.5085 | 0.086* | |
H1B | −0.0604 | 0.6504 | 0.5027 | 0.086* | |
H1C | 0.0722 | 0.7324 | 0.4899 | 0.086* | |
C24 | 0.2982 (17) | 0.6504 (7) | 0.4331 (3) | 0.112 (4) | |
H24A | 0.4064 | 0.6359 | 0.4525 | 0.168* | |
H24B | 0.2979 | 0.7202 | 0.4272 | 0.168* | |
H24C | 0.3235 | 0.6140 | 0.4083 | 0.168* | |
C25 | 0.0862 (15) | 0.6204 (7) | 0.4507 (2) | 0.080 (3) | |
H25 | −0.0229 | 0.6481 | 0.4330 | 0.096* | |
C26 | 0.052 (2) | 0.5106 (9) | 0.4533 (3) | 0.089 (3) | |
C27 | −0.137 (3) | 0.4718 (12) | 0.4402 (3) | 0.118 (4) | |
H27 | −0.2434 | 0.5136 | 0.4311 | 0.141* | |
C28 | −0.167 (3) | 0.3681 (16) | 0.4406 (5) | 0.156 (7) | |
H28 | −0.2905 | 0.3402 | 0.4308 | 0.187* | |
C29 | −0.013 (5) | 0.3101 (17) | 0.4558 (7) | 0.199 (12) | |
H29 | −0.0343 | 0.2420 | 0.4569 | 0.239* | |
C30 | 0.172 (4) | 0.3467 (16) | 0.4694 (5) | 0.183 (8) | |
H30 | 0.2774 | 0.3049 | 0.4790 | 0.220* | |
C31 | 0.199 (3) | 0.4492 (12) | 0.4686 (3) | 0.136 (5) | |
H31 | 0.3220 | 0.4762 | 0.4790 | 0.164* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.084 (15) | 0.076 (16) | 0.089 (13) | 0.019 (13) | 0.019 (13) | 0.013 (13) |
O2 | 0.087 (5) | 0.098 (4) | 0.075 (4) | −0.001 (4) | 0.010 (3) | 0.036 (3) |
O3 | 0.082 (5) | 0.145 (6) | 0.069 (4) | 0.034 (5) | 0.001 (4) | 0.030 (4) |
C14 | 0.093 (7) | 0.071 (5) | 0.048 (5) | 0.003 (5) | −0.018 (5) | 0.009 (4) |
O1D | 0.069 (12) | 0.073 (17) | 0.080 (14) | 0.004 (13) | 0.017 (12) | 0.005 (13) |
O2D | 0.087 (5) | 0.098 (4) | 0.075 (4) | −0.001 (4) | 0.010 (3) | 0.036 (3) |
O3D | 0.082 (5) | 0.145 (6) | 0.069 (4) | 0.034 (5) | 0.001 (4) | 0.030 (4) |
C14D | 0.093 (7) | 0.071 (5) | 0.048 (5) | 0.003 (5) | −0.018 (5) | 0.009 (4) |
O1P | 0.069 (14) | 0.080 (18) | 0.079 (16) | 0.010 (15) | 0.017 (14) | 0.017 (14) |
O2P | 0.087 (5) | 0.098 (4) | 0.075 (4) | −0.001 (4) | 0.010 (3) | 0.036 (3) |
O3P | 0.082 (5) | 0.145 (6) | 0.069 (4) | 0.034 (5) | 0.001 (4) | 0.030 (4) |
C14P | 0.093 (7) | 0.071 (5) | 0.048 (5) | 0.003 (5) | −0.018 (5) | 0.009 (4) |
O2Z | 0.087 (5) | 0.098 (4) | 0.075 (4) | −0.001 (4) | 0.010 (3) | 0.036 (3) |
O3Z | 0.082 (5) | 0.145 (6) | 0.069 (4) | 0.034 (5) | 0.001 (4) | 0.030 (4) |
C14Z | 0.093 (7) | 0.071 (5) | 0.048 (5) | 0.003 (5) | −0.018 (5) | 0.009 (4) |
N1 | 0.070 (5) | 0.092 (5) | 0.052 (4) | 0.007 (4) | 0.000 (4) | 0.016 (4) |
C24 | 0.123 (10) | 0.145 (9) | 0.068 (6) | 0.003 (9) | 0.030 (7) | 0.005 (6) |
C25 | 0.086 (8) | 0.103 (8) | 0.051 (6) | 0.008 (6) | −0.014 (5) | 0.005 (5) |
C26 | 0.109 (10) | 0.099 (9) | 0.058 (6) | 0.006 (9) | 0.001 (7) | 0.001 (6) |
C27 | 0.114 (12) | 0.135 (13) | 0.104 (9) | −0.001 (10) | 0.024 (8) | −0.019 (8) |
C28 | 0.171 (19) | 0.165 (18) | 0.131 (13) | −0.068 (15) | 0.032 (12) | −0.044 (12) |
C29 | 0.29 (4) | 0.129 (17) | 0.17 (2) | −0.03 (2) | 0.04 (2) | −0.001 (13) |
C30 | 0.24 (3) | 0.132 (18) | 0.178 (16) | 0.032 (15) | −0.020 (16) | 0.017 (12) |
C31 | 0.201 (17) | 0.103 (10) | 0.105 (9) | 0.006 (11) | −0.031 (10) | 0.002 (8) |
O1—C7 | 1.21 (2) | C3P—H3P | 0.9506 |
O2—C14 | 1.265 (9) | C4P—C5P | 1.3902 |
O3—C14 | 1.233 (9) | C4P—C18P | 1.52 (2) |
C6—C5 | 1.3848 | C5P—H5P | 0.9502 |
C6—C1 | 1.3949 | C7P—C8P | 1.53 (2) |
C6—C21 | 1.51 (2) | C7P—C15P | 1.66 (2) |
C1—C2 | 1.3963 | C8P—C13P | 1.3902 |
C1—C7 | 1.52 (2) | C8P—C9P | 1.3908 |
C2—C3 | 1.3968 | C9P—C10P | 1.3882 |
C2—C15 | 1.51 (2) | C9P—H9P | 0.9497 |
C3—C4 | 1.3776 | C10P—C11P | 1.3908 |
C3—H3 | 0.9300 | C10P—H10P | 0.9502 |
C4—C5 | 1.3849 | C11P—C12P | 1.3878 |
C4—C18 | 1.577 (19) | C11P—C14P | 1.522 (15) |
C5—H5 | 0.9300 | C12P—C13P | 1.3906 |
C7—C8 | 1.490 (19) | C12P—H12P | 0.9500 |
C8—C13 | 1.3777 | C13P—H13P | 0.9501 |
C8—C9 | 1.3818 | C15P—C16P | 1.51 (2) |
C9—C10 | 1.3730 | C15P—C17P | 1.54 (2) |
C9—H9 | 0.9300 | C16P—H16G | 0.9600 |
C10—C11 | 1.3822 | C16P—H16H | 0.9600 |
C10—H10 | 0.9300 | C16P—H16I | 0.9600 |
C11—C12 | 1.3734 | C17P—H17G | 0.9600 |
C11—C14 | 1.521 (15) | C17P—H17H | 0.9600 |
C12—C13 | 1.3828 | C17P—H17I | 0.9600 |
C12—H12 | 0.9300 | C18P—C19P | 1.51 (3) |
C13—H13 | 0.9300 | C18P—C20P | 1.53 (3) |
C15—C16 | 1.49 (2) | C18P—H18P | 0.9800 |
C15—C17 | 1.50 (2) | C19P—H19G | 0.9600 |
C15—H15 | 0.9800 | C19P—H19H | 0.9600 |
C16—H16A | 0.9600 | C19P—H19I | 0.9600 |
C16—H16B | 0.9600 | C20P—H20G | 0.9600 |
C16—H16C | 0.9600 | C20P—H20H | 0.9600 |
C17—H17A | 0.9600 | C20P—H20I | 0.9600 |
C17—H17B | 0.9600 | C21P—C22P | 1.54 (3) |
C17—H17C | 0.9600 | C21P—C23P | 1.54 (3) |
C18—C20 | 1.47 (2) | C21P—H21P | 0.9800 |
C18—C19 | 1.52 (2) | C22P—H22F | 0.9600 |
C18—H18 | 0.9800 | C22P—H22G | 0.9600 |
C19—H19A | 0.9600 | C22P—H22H | 0.9600 |
C19—H19B | 0.9600 | C23P—H23G | 0.9600 |
C19—H19C | 0.9600 | C23P—H23H | 0.9600 |
C20—H20A | 0.9600 | C23P—H23I | 0.9600 |
C20—H20B | 0.9600 | O1Z—C7Z | 1.42 (2) |
C20—H20C | 0.9600 | O2Z—C14Z | 1.265 (9) |
C21—C22 | 1.52 (2) | O3Z—C14Z | 1.233 (9) |
C21—C23 | 1.57 (2) | C6Z—C5Z | 1.3894 |
C21—H21 | 0.9800 | C6Z—C1Z | 1.3921 |
C22—H22A | 0.9600 | C6Z—C21Z | 1.51 (2) |
C22—H22B | 0.9600 | C1Z—C2Z | 1.3891 |
C22—H22C | 0.9600 | C1Z—C7Z | 1.52 (2) |
C23—H23A | 0.9600 | C2Z—C3Z | 1.3894 |
C23—H23B | 0.9600 | C2Z—C15Z | 1.49 (2) |
C23—H23C | 0.9600 | C3Z—C4Z | 1.3886 |
O1D—C7D | 1.46 (2) | C3Z—H3Z | 0.9504 |
O2D—C14D | 1.265 (9) | C4Z—C5Z | 1.3901 |
O3D—C14D | 1.233 (9) | C4Z—C18Z | 1.51 (2) |
C1D—C2D | 1.351 (19) | C5Z—H5Z | 0.9508 |
C1D—C6D | 1.403 (19) | C7Z—C8Z | 1.54 (2) |
C1D—C7D | 1.56 (2) | C7Z—C21Z | 1.65 (2) |
C2D—C3D | 1.39 (2) | C8Z—C13Z | 1.3906 |
C2D—C15D | 1.53 (2) | C8Z—C9Z | 1.3920 |
C3D—C4D | 1.41 (2) | C9Z—C10Z | 1.3876 |
C3D—H3D | 0.9300 | C9Z—H9Z | 0.9485 |
C4D—C5D | 1.40 (2) | C10Z—C11Z | 1.3920 |
C4D—C18D | 1.55 (2) | C10Z—H10Z | 0.9502 |
C5D—C6D | 1.389 (18) | C11Z—C12Z | 1.3869 |
C5D—H5D | 0.9300 | C11Z—C14Z | 1.565 (18) |
C6D—C21D | 1.52 (2) | C12Z—C13Z | 1.3948 |
C7D—C22D | 1.50 (2) | C12Z—H12Z | 0.9481 |
C7D—C8D | 1.539 (19) | C13Z—H13Z | 0.9480 |
C9D—C10D | 1.377 (18) | C15Z—C17Z | 1.47 (3) |
C9D—C8D | 1.387 (19) | C15Z—C16Z | 1.49 (3) |
C9D—H9D | 0.9300 | C15Z—H15Z | 0.9800 |
C8D—C13D | 1.354 (19) | C16Z—H16J | 0.9600 |
C13D—C12D | 1.373 (18) | C16Z—H16K | 0.9600 |
C13D—H13D | 0.9300 | C16Z—H16L | 0.9600 |
C12D—C11D | 1.411 (19) | C17Z—H17J | 0.9600 |
C12D—H12D | 0.9300 | C17Z—H17K | 0.9600 |
C11D—C10D | 1.379 (19) | C17Z—H17L | 0.9600 |
C11D—C14D | 1.472 (17) | C18Z—C20Z | 1.54 (3) |
C10D—H10D | 0.9300 | C18Z—C19Z | 1.54 (3) |
C15D—C16D | 1.48 (2) | C18Z—H18Z | 0.9800 |
C15D—C17D | 1.54 (2) | C19Z—H19J | 0.9600 |
C15D—H15D | 0.9800 | C19Z—H19K | 0.9600 |
C16D—H16D | 0.9600 | C19Z—H19L | 0.9600 |
C16D—H16E | 0.9600 | C20Z—H20J | 0.9600 |
C16D—H16F | 0.9600 | C20Z—H20K | 0.9600 |
C17D—H17D | 0.9600 | C20Z—H20L | 0.9600 |
C17D—H17E | 0.9600 | C21Z—C23Z | 1.52 (2) |
C17D—H17F | 0.9600 | C21Z—C22Z | 1.52 (2) |
C18D—C20D | 1.48 (2) | C22Z—H22I | 0.9600 |
C18D—C19D | 1.48 (2) | C22Z—H22J | 0.9600 |
C18D—H18D | 0.9800 | C22Z—H22K | 0.9600 |
C19D—H19D | 0.9600 | C23Z—H23J | 0.9600 |
C19D—H19E | 0.9600 | C23Z—H23K | 0.9600 |
C19D—H19F | 0.9600 | C23Z—H23L | 0.9600 |
C20D—H20D | 0.9600 | N1—C25 | 1.499 (9) |
C20D—H20E | 0.9600 | N1—H1A | 0.8900 |
C20D—H20F | 0.9600 | N1—H1B | 0.8900 |
C21D—C23D | 1.49 (2) | N1—H1C | 0.8900 |
C21D—C22D | 1.55 (2) | C24—C25 | 1.526 (12) |
C21D—H21D | 0.9800 | C24—H24A | 0.9600 |
C22D—H22D | 0.9700 | C24—H24B | 0.9600 |
C22D—H22E | 0.9700 | C24—H24C | 0.9600 |
C23D—H23D | 0.9600 | C25—C26 | 1.499 (13) |
C23D—H23E | 0.9600 | C25—H25 | 0.9800 |
C23D—H23F | 0.9600 | C26—C31 | 1.346 (15) |
O1P—C7P | 1.41 (2) | C26—C27 | 1.387 (16) |
O2P—C14P | 1.265 (9) | C27—C28 | 1.410 (17) |
O3P—C14P | 1.233 (9) | C27—H27 | 0.9300 |
C6P—C1P | 1.3892 | C28—C29 | 1.35 (2) |
C6P—C5P | 1.3911 | C28—H28 | 0.9300 |
C6P—C21P | 1.52 (2) | C29—C30 | 1.35 (2) |
C1P—C2P | 1.3907 | C29—H29 | 0.9300 |
C1P—C7P | 1.52 (2) | C30—C31 | 1.393 (18) |
C2P—C3P | 1.3909 | C30—H30 | 0.9300 |
C2P—C15P | 1.50 (2) | C31—H31 | 0.9300 |
C3P—C4P | 1.3861 | ||
C5—C6—C1 | 118.2 | C1P—C7P—C8P | 118 (2) |
C5—C6—C21 | 121.6 (15) | O1P—C7P—C15P | 117 (3) |
C1—C6—C21 | 119.9 (15) | C1P—C7P—C15P | 85.0 (16) |
C6—C1—C2 | 121.0 | C8P—C7P—C15P | 108.9 (18) |
C6—C1—C7 | 114.4 (14) | C13P—C8P—C9P | 119.9 |
C2—C1—C7 | 124.4 (15) | C13P—C8P—C7P | 121.4 (17) |
C1—C2—C3 | 118.19 (6) | C9P—C8P—C7P | 118.6 (17) |
C1—C2—C15 | 117.8 (18) | C10P—C9P—C8P | 120.0 |
C3—C2—C15 | 123.9 (18) | C10P—C9P—H9P | 120.1 |
C4—C3—C2 | 122.2 | C8P—C9P—H9P | 119.9 |
C4—C3—H3 | 118.9 | C9P—C10P—C11P | 120.1 |
C2—C3—H3 | 118.9 | C9P—C10P—H10P | 119.9 |
C3—C4—C5 | 117.8 | C11P—C10P—H10P | 120.0 |
C3—C4—C18 | 119.5 (16) | C12P—C11P—C10P | 120.0 |
C5—C4—C18 | 122.6 (16) | C12P—C11P—C14P | 117.3 (19) |
C6—C5—C4 | 122.59 (5) | C10P—C11P—C14P | 122.7 (19) |
C6—C5—H5 | 118.7 | C11P—C12P—C13P | 120.0 |
C4—C5—H5 | 118.7 | C11P—C12P—H12P | 120.1 |
O1—C7—C8 | 119 (2) | C13P—C12P—H12P | 119.9 |
O1—C7—C1 | 123 (3) | C8P—C13P—C12P | 120.0 |
C8—C7—C1 | 118 (2) | C8P—C13P—H13P | 120.0 |
C13—C8—C9 | 118.6 | C12P—C13P—H13P | 120.0 |
C13—C8—C7 | 123.3 (16) | O3P—C14P—O2P | 122.6 (7) |
C9—C8—C7 | 118.1 (16) | O3P—C14P—C11P | 120.0 (14) |
C10—C9—C8 | 120.5 | O2P—C14P—C11P | 116.2 (14) |
C10—C9—H9 | 119.8 | C2P—C15P—C16P | 125 (3) |
C8—C9—H9 | 119.8 | C2P—C15P—C17P | 114 (3) |
C9—C10—C11 | 121.0 | C16P—C15P—C17P | 107 (3) |
C9—C10—H10 | 119.5 | C2P—C15P—C7P | 84.7 (16) |
C11—C10—H10 | 119.5 | C16P—C15P—C7P | 110 (3) |
C12—C11—C10 | 118.6 | C17P—C15P—C7P | 114 (3) |
C12—C11—C14 | 119.0 (16) | C15P—C16P—H16G | 109.5 |
C10—C11—C14 | 122.2 (16) | C15P—C16P—H16H | 109.5 |
C11—C12—C13 | 120.5 | H16G—C16P—H16H | 109.5 |
C11—C12—H12 | 119.8 | C15P—C16P—H16I | 109.5 |
C13—C12—H12 | 119.8 | H16G—C16P—H16I | 109.5 |
C8—C13—C12 | 120.8 | H16H—C16P—H16I | 109.5 |
C8—C13—H13 | 119.6 | C15P—C17P—H17G | 109.5 |
C12—C13—H13 | 119.6 | C15P—C17P—H17H | 109.5 |
O3—C14—O2 | 122.6 (7) | H17G—C17P—H17H | 109.5 |
O3—C14—C11 | 119.8 (13) | C15P—C17P—H17I | 109.5 |
O2—C14—C11 | 117.5 (13) | H17G—C17P—H17I | 109.5 |
C16—C15—C17 | 115 (3) | H17H—C17P—H17I | 109.5 |
C16—C15—C2 | 116 (3) | C19P—C18P—C4P | 112 (3) |
C17—C15—C2 | 113 (2) | C19P—C18P—C20P | 112 (3) |
C16—C15—H15 | 103.6 | C4P—C18P—C20P | 99 (3) |
C17—C15—H15 | 103.6 | C19P—C18P—H18P | 111.1 |
C2—C15—H15 | 103.6 | C4P—C18P—H18P | 111.1 |
C15—C16—H16A | 109.5 | C20P—C18P—H18P | 111.1 |
C15—C16—H16B | 109.5 | C18P—C19P—H19G | 109.5 |
H16A—C16—H16B | 109.5 | C18P—C19P—H19H | 109.5 |
C15—C16—H16C | 109.5 | H19G—C19P—H19H | 109.5 |
H16A—C16—H16C | 109.5 | C18P—C19P—H19I | 109.5 |
H16B—C16—H16C | 109.5 | H19G—C19P—H19I | 109.5 |
C15—C17—H17A | 109.5 | H19H—C19P—H19I | 109.5 |
C15—C17—H17B | 109.5 | C18P—C20P—H20G | 109.5 |
H17A—C17—H17B | 109.5 | C18P—C20P—H20H | 109.5 |
C15—C17—H17C | 109.5 | H20G—C20P—H20H | 109.5 |
H17A—C17—H17C | 109.5 | C18P—C20P—H20I | 109.5 |
H17B—C17—H17C | 109.5 | H20G—C20P—H20I | 109.5 |
C20—C18—C19 | 111 (3) | H20H—C20P—H20I | 109.5 |
C20—C18—C4 | 112 (3) | C6P—C21P—C22P | 111 (3) |
C19—C18—C4 | 113 (2) | C6P—C21P—C23P | 114 (3) |
C20—C18—H18 | 106.9 | C22P—C21P—C23P | 107 (3) |
C19—C18—H18 | 106.9 | C6P—C21P—H21P | 108.3 |
C4—C18—H18 | 106.9 | C22P—C21P—H21P | 108.3 |
C18—C19—H19A | 109.5 | C23P—C21P—H21P | 108.3 |
C18—C19—H19B | 109.5 | C21P—C22P—H22F | 109.5 |
H19A—C19—H19B | 109.5 | C21P—C22P—H22G | 109.5 |
C18—C19—H19C | 109.5 | H22F—C22P—H22G | 109.5 |
H19A—C19—H19C | 109.5 | C21P—C22P—H22H | 109.5 |
H19B—C19—H19C | 109.5 | H22F—C22P—H22H | 109.5 |
C18—C20—H20A | 109.5 | H22G—C22P—H22H | 109.5 |
C18—C20—H20B | 109.5 | C21P—C23P—H23G | 109.5 |
H20A—C20—H20B | 109.5 | C21P—C23P—H23H | 109.5 |
C18—C20—H20C | 109.5 | H23G—C23P—H23H | 109.5 |
H20A—C20—H20C | 109.5 | C21P—C23P—H23I | 109.5 |
H20B—C20—H20C | 109.5 | H23G—C23P—H23I | 109.5 |
C6—C21—C22 | 111 (2) | H23H—C23P—H23I | 109.5 |
C6—C21—C23 | 107 (2) | C5Z—C6Z—C1Z | 120.0 |
C22—C21—C23 | 108 (2) | C5Z—C6Z—C21Z | 145.1 (17) |
C6—C21—H21 | 110.2 | C1Z—C6Z—C21Z | 94.9 (17) |
C22—C21—H21 | 110.2 | C2Z—C1Z—C6Z | 119.8 |
C23—C21—H21 | 110.2 | C2Z—C1Z—C7Z | 144.9 (17) |
C21—C22—H22A | 109.5 | C6Z—C1Z—C7Z | 94.6 (17) |
C21—C22—H22B | 109.5 | C1Z—C2Z—C3Z | 120.20 (7) |
H22A—C22—H22B | 109.5 | C1Z—C2Z—C15Z | 118 (2) |
C21—C22—H22C | 109.5 | C3Z—C2Z—C15Z | 121 (2) |
H22A—C22—H22C | 109.5 | C4Z—C3Z—C2Z | 119.9 |
H22B—C22—H22C | 109.5 | C4Z—C3Z—H3Z | 120.0 |
C21—C23—H23A | 109.5 | C2Z—C3Z—H3Z | 120.0 |
C21—C23—H23B | 109.5 | C3Z—C4Z—C5Z | 120.0 |
H23A—C23—H23B | 109.5 | C3Z—C4Z—C18Z | 114 (2) |
C21—C23—H23C | 109.5 | C5Z—C4Z—C18Z | 126 (2) |
H23A—C23—H23C | 109.5 | C6Z—C5Z—C4Z | 120.05 (7) |
H23B—C23—H23C | 109.5 | C6Z—C5Z—H5Z | 120.0 |
C2D—C1D—C6D | 121.3 (17) | C4Z—C5Z—H5Z | 120.0 |
C2D—C1D—C7D | 126.2 (18) | O1Z—C7Z—C1Z | 97 (3) |
C6D—C1D—C7D | 112.5 (16) | O1Z—C7Z—C8Z | 114 (3) |
C1D—C2D—C3D | 119.9 (17) | C1Z—C7Z—C8Z | 120 (3) |
C1D—C2D—C15D | 122 (2) | O1Z—C7Z—C21Z | 113 (3) |
C3D—C2D—C15D | 117.5 (19) | C1Z—C7Z—C21Z | 85.2 (16) |
C2D—C3D—C4D | 120.9 (18) | C8Z—C7Z—C21Z | 123 (2) |
C2D—C3D—H3D | 119.5 | C13Z—C8Z—C9Z | 120.1 |
C4D—C3D—H3D | 119.5 | C13Z—C8Z—C7Z | 121 (2) |
C5D—C4D—C3D | 117.2 (17) | C9Z—C8Z—C7Z | 119 (2) |
C5D—C4D—C18D | 114 (2) | C10Z—C9Z—C8Z | 120.0 |
C3D—C4D—C18D | 129 (2) | C10Z—C9Z—H9Z | 119.8 |
C6D—C5D—C4D | 121.7 (19) | C8Z—C9Z—H9Z | 120.2 |
C6D—C5D—H5D | 119.2 | C9Z—C10Z—C11Z | 119.9 |
C4D—C5D—H5D | 119.2 | C9Z—C10Z—H10Z | 120.4 |
C5D—C6D—C1D | 118.6 (17) | C11Z—C10Z—H10Z | 119.8 |
C5D—C6D—C21D | 133.4 (19) | C12Z—C11Z—C10Z | 120.4 |
C1D—C6D—C21D | 108.1 (16) | C12Z—C11Z—C14Z | 116 (2) |
O1D—C7D—C22D | 109.2 (19) | C10Z—C11Z—C14Z | 124 (2) |
O1D—C7D—C8D | 109.0 (19) | C11Z—C12Z—C13Z | 119.8 |
C22D—C7D—C8D | 116 (2) | C11Z—C12Z—H12Z | 120.5 |
O1D—C7D—C1D | 110 (2) | C13Z—C12Z—H12Z | 119.7 |
C22D—C7D—C1D | 99.6 (15) | C8Z—C13Z—C12Z | 119.9 |
C8D—C7D—C1D | 113 (2) | C8Z—C13Z—H13Z | 120.1 |
C10D—C9D—C8D | 117.8 (18) | C12Z—C13Z—H13Z | 120.0 |
C10D—C9D—H9D | 121.1 | O3Z—C14Z—O2Z | 122.6 (7) |
C8D—C9D—H9D | 121.1 | O3Z—C14Z—C11Z | 119.9 (15) |
C13D—C8D—C9D | 119.1 (16) | O2Z—C14Z—C11Z | 117.4 (15) |
C13D—C8D—C7D | 121.9 (19) | C17Z—C15Z—C16Z | 116 (4) |
C9D—C8D—C7D | 119.0 (18) | C17Z—C15Z—C2Z | 117 (3) |
C8D—C13D—C12D | 123.4 (19) | C16Z—C15Z—C2Z | 104 (2) |
C8D—C13D—H13D | 118.3 | C17Z—C15Z—H15Z | 106.2 |
C12D—C13D—H13D | 118.3 | C16Z—C15Z—H15Z | 106.2 |
C13D—C12D—C11D | 119.0 (18) | C2Z—C15Z—H15Z | 106.2 |
C13D—C12D—H12D | 120.5 | C15Z—C16Z—H16J | 109.5 |
C11D—C12D—H12D | 120.5 | C15Z—C16Z—H16K | 109.5 |
C10D—C11D—C12D | 116.3 (16) | H16J—C16Z—H16K | 109.5 |
C10D—C11D—C14D | 121.2 (18) | C15Z—C16Z—H16L | 109.5 |
C12D—C11D—C14D | 122.3 (18) | H16J—C16Z—H16L | 109.5 |
C9D—C10D—C11D | 124.5 (18) | H16K—C16Z—H16L | 109.5 |
C9D—C10D—H10D | 117.8 | C15Z—C17Z—H17J | 109.5 |
C11D—C10D—H10D | 117.8 | C15Z—C17Z—H17K | 109.5 |
O3D—C14D—O2D | 122.6 (7) | H17J—C17Z—H17K | 109.5 |
O3D—C14D—C11D | 116.2 (13) | C15Z—C17Z—H17L | 109.5 |
O2D—C14D—C11D | 120.9 (12) | H17J—C17Z—H17L | 109.5 |
C16D—C15D—C2D | 108 (2) | H17K—C17Z—H17L | 109.5 |
C16D—C15D—C17D | 116 (3) | C4Z—C18Z—C20Z | 113 (3) |
C2D—C15D—C17D | 107 (2) | C4Z—C18Z—C19Z | 97 (3) |
C16D—C15D—H15D | 108.6 | C20Z—C18Z—C19Z | 107 (3) |
C2D—C15D—H15D | 108.6 | C4Z—C18Z—H18Z | 112.8 |
C17D—C15D—H15D | 108.6 | C20Z—C18Z—H18Z | 112.8 |
C15D—C16D—H16D | 109.5 | C19Z—C18Z—H18Z | 112.8 |
C15D—C16D—H16E | 109.5 | C18Z—C19Z—H19J | 109.5 |
H16D—C16D—H16E | 109.5 | C18Z—C19Z—H19K | 109.5 |
C15D—C16D—H16F | 109.5 | H19J—C19Z—H19K | 109.5 |
H16D—C16D—H16F | 109.5 | C18Z—C19Z—H19L | 109.5 |
H16E—C16D—H16F | 109.5 | H19J—C19Z—H19L | 109.5 |
C15D—C17D—H17D | 109.5 | H19K—C19Z—H19L | 109.5 |
C15D—C17D—H17E | 109.5 | C18Z—C20Z—H20J | 109.5 |
H17D—C17D—H17E | 109.5 | C18Z—C20Z—H20K | 109.5 |
C15D—C17D—H17F | 109.5 | H20J—C20Z—H20K | 109.5 |
H17D—C17D—H17F | 109.5 | C18Z—C20Z—H20L | 109.5 |
H17E—C17D—H17F | 109.5 | H20J—C20Z—H20L | 109.5 |
C20D—C18D—C19D | 120 (2) | H20K—C20Z—H20L | 109.5 |
C20D—C18D—C4D | 117 (2) | C6Z—C21Z—C23Z | 121 (3) |
C19D—C18D—C4D | 122 (2) | C6Z—C21Z—C22Z | 107 (3) |
C20D—C18D—H18D | 93.3 | C23Z—C21Z—C22Z | 112 (3) |
C19D—C18D—H18D | 93.3 | C6Z—C21Z—C7Z | 85.0 (17) |
C4D—C18D—H18D | 93.3 | C23Z—C21Z—C7Z | 114 (3) |
C18D—C19D—H19D | 109.5 | C22Z—C21Z—C7Z | 114 (3) |
C18D—C19D—H19E | 109.5 | C21Z—C22Z—H22I | 109.5 |
H19D—C19D—H19E | 109.5 | C21Z—C22Z—H22J | 109.5 |
C18D—C19D—H19F | 109.5 | H22I—C22Z—H22J | 109.5 |
H19D—C19D—H19F | 109.5 | C21Z—C22Z—H22K | 109.5 |
H19E—C19D—H19F | 109.5 | H22I—C22Z—H22K | 109.5 |
C18D—C20D—H20D | 109.5 | H22J—C22Z—H22K | 109.5 |
C18D—C20D—H20E | 109.5 | C21Z—C23Z—H23J | 109.5 |
H20D—C20D—H20E | 109.5 | C21Z—C23Z—H23K | 109.5 |
C18D—C20D—H20F | 109.5 | H23J—C23Z—H23K | 109.5 |
H20D—C20D—H20F | 109.5 | C21Z—C23Z—H23L | 109.5 |
H20E—C20D—H20F | 109.5 | H23J—C23Z—H23L | 109.5 |
C23D—C21D—C6D | 118 (2) | H23K—C23Z—H23L | 109.5 |
C23D—C21D—C22D | 116 (3) | C25—N1—H1A | 109.5 |
C6D—C21D—C22D | 101.5 (18) | C25—N1—H1B | 109.5 |
C23D—C21D—H21D | 107.0 | H1A—N1—H1B | 109.5 |
C6D—C21D—H21D | 107.0 | C25—N1—H1C | 109.5 |
C22D—C21D—H21D | 107.0 | H1A—N1—H1C | 109.5 |
C7D—C22D—C21D | 108.4 (16) | H1B—N1—H1C | 109.5 |
C7D—C22D—H22D | 110.0 | C25—C24—H24A | 109.5 |
C21D—C22D—H22D | 110.0 | C25—C24—H24B | 109.5 |
C7D—C22D—H22E | 110.0 | H24A—C24—H24B | 109.5 |
C21D—C22D—H22E | 110.0 | C25—C24—H24C | 109.5 |
H22D—C22D—H22E | 108.4 | H24A—C24—H24C | 109.5 |
C21D—C23D—H23D | 109.5 | H24B—C24—H24C | 109.5 |
C21D—C23D—H23E | 109.5 | C26—C25—N1 | 110.3 (7) |
H23D—C23D—H23E | 109.5 | C26—C25—C24 | 114.3 (9) |
C21D—C23D—H23F | 109.5 | N1—C25—C24 | 108.5 (7) |
H23D—C23D—H23F | 109.5 | C26—C25—H25 | 107.8 |
H23E—C23D—H23F | 109.5 | N1—C25—H25 | 107.8 |
C1P—C6P—C5P | 120.0 | C24—C25—H25 | 107.8 |
C1P—C6P—C21P | 126 (2) | C31—C26—C27 | 119.4 (12) |
C5P—C6P—C21P | 114 (2) | C31—C26—C25 | 121.8 (13) |
C6P—C1P—C2P | 120.0 | C27—C26—C25 | 118.8 (13) |
C6P—C1P—C7P | 145.6 (17) | C26—C27—C28 | 119.3 (15) |
C2P—C1P—C7P | 94.3 (17) | C26—C27—H27 | 120.4 |
C1P—C2P—C3P | 119.91 (7) | C28—C27—H27 | 120.4 |
C1P—C2P—C15P | 95.7 (17) | C29—C28—C27 | 118 (2) |
C3P—C2P—C15P | 144.3 (17) | C29—C28—H28 | 120.8 |
C4P—C3P—C2P | 120.1 | C27—C28—H28 | 120.8 |
C4P—C3P—H3P | 120.1 | C28—C29—C30 | 123 (3) |
C2P—C3P—H3P | 119.8 | C28—C29—H29 | 118.4 |
C3P—C4P—C5P | 120.1 | C30—C29—H29 | 118.4 |
C3P—C4P—C18P | 122 (2) | C29—C30—C31 | 117 (2) |
C5P—C4P—C18P | 118 (2) | C29—C30—H30 | 121.3 |
C4P—C5P—C6P | 119.92 (6) | C31—C30—H30 | 121.3 |
C4P—C5P—H5P | 120.1 | C26—C31—C30 | 122.2 (16) |
C6P—C5P—H5P | 120.0 | C26—C31—H31 | 118.9 |
O1P—C7P—C1P | 122 (3) | C30—C31—H31 | 118.9 |
O1P—C7P—C8P | 105 (2) |
C31H39NO3 | Dx = 1.120 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 1909 reflections |
a = 6.392 (1) Å | θ = 1.6–18.2° |
b = 13.4462 (18) Å | µ = 0.07 mm−1 |
c = 32.676 (3) Å | T = 299 K |
V = 2808.4 (6) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.12 × 0.10 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 5427 independent reflections |
Radiation source: fine-focus sealed tube | 1825 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.138 |
ω scans | θmax = 26.0°, θmin = 1.6° |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | h = −7→7 |
Tmin = 0.878, Tmax = 1.000 | k = −14→16 |
25062 measured reflections | l = −40→40 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.091 | H-atom parameters constrained |
wR(F2) = 0.219 | w = 1/[σ2(Fo2) + (0.0453P)2 + 0.3835P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
5427 reflections | Δρmax = 0.14 e Å−3 |
450 parameters | Δρmin = −0.16 e Å−3 |
537 restraints | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 2.6 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 1.052 (6) | 0.241 (3) | 0.6361 (14) | 0.079 (9) | 0.264 (4) |
O2 | 0.6597 (10) | 0.6317 (4) | 0.51834 (17) | 0.0885 (19) | 0.264 (4) |
O3 | 0.3579 (11) | 0.6152 (5) | 0.54952 (17) | 0.098 (2) | 0.264 (4) |
C1 | 0.836 (8) | 0.282 (3) | 0.6944 (9) | 0.065 (12)* | 0.264 (4) |
C6 | 0.703 (7) | 0.202 (3) | 0.6996 (9) | 0.071 (11)* | 0.264 (4) |
C5 | 0.626 (8) | 0.183 (3) | 0.7388 (9) | 0.077 (12)* | 0.264 (4) |
H5 | 0.5453 | 0.1266 | 0.7431 | 0.092* | 0.264 (4) |
C4 | 0.666 (6) | 0.245 (3) | 0.7714 (8) | 0.065 (11)* | 0.264 (4) |
C3 | 0.789 (7) | 0.328 (3) | 0.7652 (11) | 0.077 (11)* | 0.264 (4) |
H3 | 0.8160 | 0.3715 | 0.7868 | 0.092* | 0.264 (4) |
C2 | 0.875 (8) | 0.348 (3) | 0.7267 (10) | 0.074 (12)* | 0.264 (4) |
C7 | 0.919 (5) | 0.293 (2) | 0.6511 (9) | 0.079 (11)* | 0.264 (4) |
C8 | 0.822 (5) | 0.373 (2) | 0.6252 (9) | 0.058 (10)* | 0.264 (4) |
C13 | 0.623 (6) | 0.408 (3) | 0.6308 (11) | 0.056 (11)* | 0.264 (4) |
H13 | 0.5464 | 0.3827 | 0.6528 | 0.067* | 0.264 (4) |
C9 | 0.932 (5) | 0.410 (2) | 0.5930 (9) | 0.054 (9)* | 0.264 (4) |
H9 | 1.0676 | 0.3888 | 0.5882 | 0.065* | 0.264 (4) |
C10 | 0.842 (5) | 0.480 (2) | 0.5672 (10) | 0.072 (11)* | 0.264 (4) |
H10 | 0.9201 | 0.5044 | 0.5454 | 0.087* | 0.264 (4) |
C11 | 0.642 (5) | 0.5152 (12) | 0.5726 (8) | 0.065 (12)* | 0.264 (4) |
C12 | 0.529 (6) | 0.478 (2) | 0.6057 (10) | 0.069 (12)* | 0.264 (4) |
H12 | 0.3929 | 0.4989 | 0.6107 | 0.083* | 0.264 (4) |
C14 | 0.5418 (16) | 0.5921 (6) | 0.5448 (2) | 0.073 (2) | 0.264 (4) |
C15 | 1.011 (6) | 0.438 (2) | 0.7203 (14) | 0.078 (11)* | 0.264 (4) |
H15 | 0.9939 | 0.4517 | 0.6910 | 0.094* | 0.264 (4) |
C16 | 1.242 (6) | 0.424 (5) | 0.724 (2) | 0.064 (16)* | 0.264 (4) |
H16A | 1.2812 | 0.3619 | 0.7114 | 0.095* | 0.264 (4) |
H16B | 1.3142 | 0.4774 | 0.7110 | 0.095* | 0.264 (4) |
H16C | 1.2802 | 0.4216 | 0.7526 | 0.095* | 0.264 (4) |
C17 | 0.936 (7) | 0.533 (3) | 0.7395 (13) | 0.104 (14)* | 0.264 (4) |
H17A | 0.7868 | 0.5387 | 0.7361 | 0.156* | 0.264 (4) |
H17B | 0.9688 | 0.5331 | 0.7682 | 0.156* | 0.264 (4) |
H17C | 1.0027 | 0.5889 | 0.7266 | 0.156* | 0.264 (4) |
C18 | 0.576 (5) | 0.233 (4) | 0.8145 (9) | 0.099 (12)* | 0.264 (4) |
H18 | 0.5679 | 0.1605 | 0.8169 | 0.119* | 0.264 (4) |
C19 | 0.699 (5) | 0.259 (3) | 0.8509 (9) | 0.067 (11)* | 0.264 (4) |
H19A | 0.8418 | 0.2383 | 0.8470 | 0.100* | 0.264 (4) |
H19B | 0.6949 | 0.3296 | 0.8551 | 0.100* | 0.264 (4) |
H19C | 0.6425 | 0.2258 | 0.8744 | 0.100* | 0.264 (4) |
C20 | 0.349 (4) | 0.261 (3) | 0.8166 (10) | 0.059 (10)* | 0.264 (4) |
H20A | 0.2804 | 0.2416 | 0.7917 | 0.089* | 0.264 (4) |
H20B | 0.2841 | 0.2280 | 0.8393 | 0.089* | 0.264 (4) |
H20C | 0.3365 | 0.3318 | 0.8200 | 0.089* | 0.264 (4) |
C21 | 0.648 (6) | 0.133 (2) | 0.6643 (11) | 0.079 (12)* | 0.264 (4) |
H21 | 0.6352 | 0.1713 | 0.6388 | 0.095* | 0.264 (4) |
C22 | 0.816 (7) | 0.053 (3) | 0.6601 (15) | 0.098 (15)* | 0.264 (4) |
H22A | 0.7820 | 0.0102 | 0.6377 | 0.148* | 0.264 (4) |
H22B | 0.9491 | 0.0845 | 0.6549 | 0.148* | 0.264 (4) |
H22C | 0.8241 | 0.0155 | 0.6849 | 0.148* | 0.264 (4) |
C23 | 0.439 (6) | 0.077 (4) | 0.6738 (17) | 0.088 (15)* | 0.264 (4) |
H23A | 0.4046 | 0.0339 | 0.6514 | 0.131* | 0.264 (4) |
H23B | 0.4553 | 0.0385 | 0.6983 | 0.131* | 0.264 (4) |
H23C | 0.3283 | 0.1246 | 0.6776 | 0.131* | 0.264 (4) |
O1D | 1.097 (3) | 0.271 (2) | 0.6419 (9) | 0.078 (9) | 0.400 (4) |
O2D | 0.6597 (10) | 0.6317 (4) | 0.51834 (17) | 0.0885 (19) | 0.400 (4) |
O3D | 0.3579 (11) | 0.6152 (5) | 0.54952 (17) | 0.098 (2) | 0.400 (4) |
C1D | 0.803 (5) | 0.2802 (19) | 0.6916 (6) | 0.068 (9)* | 0.400 (4) |
C2D | 0.887 (5) | 0.3438 (18) | 0.7196 (7) | 0.067 (8)* | 0.400 (4) |
C3D | 0.840 (4) | 0.331 (2) | 0.7614 (7) | 0.080 (8)* | 0.400 (4) |
H3D | 0.9044 | 0.3718 | 0.7807 | 0.097* | 0.400 (4) |
C4D | 0.697 (4) | 0.257 (2) | 0.7747 (7) | 0.077 (9)* | 0.400 (4) |
C5D | 0.609 (6) | 0.197 (2) | 0.7440 (7) | 0.074 (9)* | 0.400 (4) |
H5D | 0.5112 | 0.1484 | 0.7513 | 0.089* | 0.400 (4) |
C6D | 0.663 (6) | 0.207 (2) | 0.7033 (7) | 0.074 (9)* | 0.400 (4) |
C7D | 0.870 (3) | 0.2715 (15) | 0.6455 (6) | 0.081 (8)* | 0.400 (4) |
C9D | 0.896 (4) | 0.3909 (18) | 0.5857 (7) | 0.066 (8)* | 0.400 (4) |
H9D | 1.0276 | 0.3646 | 0.5798 | 0.079* | 0.400 (4) |
C8D | 0.780 (3) | 0.3549 (14) | 0.6184 (6) | 0.057 (7)* | 0.400 (4) |
C13D | 0.590 (4) | 0.3947 (18) | 0.6269 (8) | 0.072 (8)* | 0.400 (4) |
H13D | 0.5132 | 0.3702 | 0.6488 | 0.087* | 0.400 (4) |
C12D | 0.507 (4) | 0.4717 (18) | 0.6032 (7) | 0.071 (9)* | 0.400 (4) |
H12D | 0.3768 | 0.4982 | 0.6094 | 0.085* | 0.400 (4) |
C11D | 0.622 (3) | 0.5087 (10) | 0.5702 (5) | 0.055 (8)* | 0.400 (4) |
C10D | 0.814 (4) | 0.4663 (17) | 0.5622 (7) | 0.063 (8)* | 0.400 (4) |
H10D | 0.8912 | 0.4896 | 0.5401 | 0.076* | 0.400 (4) |
C14D | 0.5418 (16) | 0.5921 (6) | 0.5448 (2) | 0.073 (2) | 0.400 (4) |
C15D | 1.040 (4) | 0.4245 (16) | 0.7072 (8) | 0.075 (8)* | 0.400 (4) |
H15D | 1.0686 | 0.4188 | 0.6778 | 0.090* | 0.400 (4) |
C16D | 1.241 (4) | 0.409 (3) | 0.7303 (14) | 0.116 (17)* | 0.400 (4) |
H16D | 1.3397 | 0.4590 | 0.7229 | 0.174* | 0.400 (4) |
H16E | 1.2135 | 0.4121 | 0.7592 | 0.174* | 0.400 (4) |
H16F | 1.2966 | 0.3442 | 0.7237 | 0.174* | 0.400 (4) |
C17D | 0.934 (5) | 0.5261 (16) | 0.7157 (10) | 0.072 (9)* | 0.400 (4) |
H17D | 0.8080 | 0.5310 | 0.6999 | 0.107* | 0.400 (4) |
H17E | 0.9018 | 0.5313 | 0.7443 | 0.107* | 0.400 (4) |
H17F | 1.0279 | 0.5788 | 0.7081 | 0.107* | 0.400 (4) |
C18D | 0.643 (4) | 0.219 (3) | 0.8195 (7) | 0.094 (9)* | 0.400 (4) |
H18D | 0.6602 | 0.1465 | 0.8180 | 0.112* | 0.400 (4) |
C19D | 0.800 (4) | 0.251 (2) | 0.8505 (7) | 0.081 (8)* | 0.400 (4) |
H19D | 0.9386 | 0.2385 | 0.8403 | 0.121* | 0.400 (4) |
H19E | 0.7845 | 0.3212 | 0.8556 | 0.121* | 0.400 (4) |
H19F | 0.7793 | 0.2152 | 0.8755 | 0.121* | 0.400 (4) |
C20D | 0.413 (4) | 0.233 (3) | 0.8301 (12) | 0.106 (13)* | 0.400 (4) |
H20D | 0.3281 | 0.2094 | 0.8079 | 0.159* | 0.400 (4) |
H20E | 0.3804 | 0.1963 | 0.8545 | 0.159* | 0.400 (4) |
H20F | 0.3856 | 0.3023 | 0.8346 | 0.159* | 0.400 (4) |
C21D | 0.601 (5) | 0.148 (2) | 0.6652 (8) | 0.085 (10)* | 0.400 (4) |
H21D | 0.4775 | 0.1810 | 0.6536 | 0.103* | 0.400 (4) |
C22D | 0.786 (3) | 0.1701 (14) | 0.6361 (6) | 0.093 (7)* | 0.400 (4) |
H22D | 0.8946 | 0.1207 | 0.6397 | 0.111* | 0.400 (4) |
H22E | 0.7387 | 0.1675 | 0.6079 | 0.111* | 0.400 (4) |
C23D | 0.546 (5) | 0.0418 (17) | 0.6708 (8) | 0.122 (11)* | 0.400 (4) |
H23D | 0.5101 | 0.0132 | 0.6448 | 0.183* | 0.400 (4) |
H23E | 0.6635 | 0.0070 | 0.6822 | 0.183* | 0.400 (4) |
H23F | 0.4288 | 0.0365 | 0.6891 | 0.183* | 0.400 (4) |
O1P | 1.113 (6) | 0.303 (3) | 0.6526 (15) | 0.075 (9) | 0.199 (4) |
O2P | 0.6597 (10) | 0.6317 (4) | 0.51834 (17) | 0.0885 (19) | 0.199 (4) |
O3P | 0.3579 (11) | 0.6152 (5) | 0.54952 (17) | 0.098 (2) | 0.199 (4) |
C6P | 0.665 (6) | 0.212 (3) | 0.7049 (9) | 0.069 (13)* | 0.199 (4) |
C1P | 0.796 (6) | 0.293 (2) | 0.7003 (7) | 0.059 (12)* | 0.199 (4) |
C2P | 0.858 (7) | 0.348 (3) | 0.7343 (9) | 0.061 (11)* | 0.199 (4) |
C3P | 0.787 (7) | 0.321 (3) | 0.7730 (8) | 0.074 (12)* | 0.199 (4) |
H3P | 0.8291 | 0.3584 | 0.7963 | 0.089* | 0.199 (4) |
C4P | 0.656 (6) | 0.239 (3) | 0.7777 (8) | 0.077 (13)* | 0.199 (4) |
C5P | 0.595 (7) | 0.185 (3) | 0.7436 (10) | 0.079 (13)* | 0.199 (4) |
H5P | 0.5049 | 0.1290 | 0.7468 | 0.095* | 0.199 (4) |
C7P | 0.936 (4) | 0.3476 (18) | 0.6704 (7) | 0.054 (9)* | 0.199 (4) |
C8P | 0.832 (4) | 0.4084 (15) | 0.6363 (6) | 0.051 (9)* | 0.199 (4) |
C9P | 0.956 (3) | 0.4520 (19) | 0.6063 (8) | 0.074 (11)* | 0.199 (4) |
H9P | 1.1023 | 0.4411 | 0.6062 | 0.089* | 0.199 (4) |
C10P | 0.864 (4) | 0.5114 (18) | 0.5765 (7) | 0.070 (10)* | 0.199 (4) |
H10P | 0.9491 | 0.5412 | 0.5559 | 0.084* | 0.199 (4) |
C11P | 0.649 (5) | 0.5274 (15) | 0.5766 (7) | 0.075 (12)* | 0.199 (4) |
C12P | 0.526 (4) | 0.484 (2) | 0.6065 (10) | 0.069 (13)* | 0.199 (4) |
H12P | 0.3789 | 0.4947 | 0.6067 | 0.083* | 0.199 (4) |
C13P | 0.617 (4) | 0.424 (2) | 0.6365 (8) | 0.061 (12)* | 0.199 (4) |
H13P | 0.5321 | 0.3946 | 0.6570 | 0.073* | 0.199 (4) |
C14P | 0.5418 (16) | 0.5921 (6) | 0.5448 (2) | 0.073 (2) | 0.199 (4) |
C15P | 0.983 (6) | 0.421 (2) | 0.7097 (9) | 0.068 (12)* | 0.199 (4) |
C16P | 1.215 (6) | 0.433 (5) | 0.718 (2) | 0.09 (2)* | 0.199 (4) |
H16G | 1.2711 | 0.4826 | 0.6996 | 0.138* | 0.199 (4) |
H16H | 1.2362 | 0.4536 | 0.7456 | 0.138* | 0.199 (4) |
H16I | 1.2841 | 0.3709 | 0.7131 | 0.138* | 0.199 (4) |
C17P | 0.891 (10) | 0.525 (3) | 0.7037 (18) | 0.11 (2)* | 0.199 (4) |
H17G | 0.9859 | 0.5646 | 0.6876 | 0.166* | 0.199 (4) |
H17H | 0.7595 | 0.5201 | 0.6898 | 0.166* | 0.199 (4) |
H17I | 0.8711 | 0.5562 | 0.7299 | 0.166* | 0.199 (4) |
C18P | 0.581 (7) | 0.206 (3) | 0.8196 (10) | 0.086 (13)* | 0.199 (4) |
H18P | 0.5020 | 0.1442 | 0.8185 | 0.103* | 0.199 (4) |
C19P | 0.761 (7) | 0.201 (3) | 0.8496 (12) | 0.070 (13)* | 0.199 (4) |
H19G | 0.7091 | 0.1801 | 0.8758 | 0.105* | 0.199 (4) |
H19H | 0.8624 | 0.1542 | 0.8399 | 0.105* | 0.199 (4) |
H19I | 0.8241 | 0.2655 | 0.8521 | 0.105* | 0.199 (4) |
C20P | 0.440 (8) | 0.297 (4) | 0.8289 (17) | 0.116 (19)* | 0.199 (4) |
H20G | 0.3272 | 0.2986 | 0.8095 | 0.175* | 0.199 (4) |
H20H | 0.3842 | 0.2906 | 0.8560 | 0.175* | 0.199 (4) |
H20I | 0.5206 | 0.3566 | 0.8268 | 0.175* | 0.199 (4) |
C21P | 0.583 (7) | 0.148 (3) | 0.6702 (14) | 0.079 (13)* | 0.199 (4) |
H21P | 0.5529 | 0.1919 | 0.6471 | 0.095* | 0.199 (4) |
C22P | 0.752 (9) | 0.074 (4) | 0.6565 (19) | 0.100 (17)* | 0.199 (4) |
H22F | 0.6993 | 0.0336 | 0.6345 | 0.149* | 0.199 (4) |
H22G | 0.8734 | 0.1097 | 0.6473 | 0.149* | 0.199 (4) |
H22H | 0.7903 | 0.0318 | 0.6791 | 0.149* | 0.199 (4) |
C23P | 0.385 (7) | 0.088 (4) | 0.679 (2) | 0.088 (19)* | 0.199 (4) |
H23G | 0.3468 | 0.0503 | 0.6552 | 0.131* | 0.199 (4) |
H23H | 0.4104 | 0.0431 | 0.7014 | 0.131* | 0.199 (4) |
H23I | 0.2730 | 0.1322 | 0.6861 | 0.131* | 0.199 (4) |
O1Z | 1.110 (7) | 0.283 (6) | 0.655 (2) | 0.075 (10)* | 0.137 (4) |
O2Z | 0.6597 (10) | 0.6317 (4) | 0.51834 (17) | 0.0885 (19) | 0.137 (4) |
O3Z | 0.3579 (11) | 0.6152 (5) | 0.54952 (17) | 0.098 (2) | 0.137 (4) |
C6Z | 0.754 (8) | 0.219 (3) | 0.7084 (9) | 0.060 (13)* | 0.137 (4) |
C1Z | 0.871 (7) | 0.304 (3) | 0.7013 (9) | 0.060 (13)* | 0.137 (4) |
C2Z | 0.902 (7) | 0.373 (3) | 0.7326 (10) | 0.073 (13)* | 0.137 (4) |
C3Z | 0.818 (7) | 0.355 (3) | 0.7712 (10) | 0.084 (14)* | 0.137 (4) |
H3Z | 0.8393 | 0.4017 | 0.7926 | 0.100* | 0.137 (4) |
C4Z | 0.702 (7) | 0.269 (3) | 0.7783 (9) | 0.078 (14)* | 0.137 (4) |
C5Z | 0.670 (7) | 0.201 (3) | 0.7470 (10) | 0.072 (14)* | 0.137 (4) |
H5Z | 0.5906 | 0.1427 | 0.7519 | 0.087* | 0.137 (4) |
C7Z | 0.888 (7) | 0.288 (2) | 0.6554 (10) | 0.083 (14)* | 0.137 (4) |
C8Z | 0.796 (7) | 0.367 (3) | 0.6258 (11) | 0.054 (14)* | 0.137 (4) |
C9Z | 0.876 (7) | 0.376 (3) | 0.5864 (13) | 0.070 (14)* | 0.137 (4) |
H9Z | 0.9852 | 0.3336 | 0.5773 | 0.084* | 0.137 (4) |
C10Z | 0.796 (7) | 0.448 (3) | 0.5601 (10) | 0.064 (14)* | 0.137 (4) |
H10Z | 0.8504 | 0.4548 | 0.5332 | 0.077* | 0.137 (4) |
C11Z | 0.636 (4) | 0.5102 (15) | 0.5733 (9) | 0.063 (14)* | 0.137 (4) |
C12Z | 0.556 (6) | 0.501 (3) | 0.6126 (11) | 0.063 (13)* | 0.137 (4) |
H12Z | 0.4468 | 0.5435 | 0.6217 | 0.076* | 0.137 (4) |
C13Z | 0.636 (7) | 0.429 (3) | 0.6389 (10) | 0.064 (13)* | 0.137 (4) |
H13Z | 0.5816 | 0.4223 | 0.6658 | 0.077* | 0.137 (4) |
C14Z | 0.5418 (16) | 0.5921 (6) | 0.5448 (2) | 0.073 (2) | 0.137 (4) |
C15Z | 1.020 (8) | 0.464 (3) | 0.7222 (19) | 0.080 (14)* | 0.137 (4) |
H15Z | 1.0476 | 0.4586 | 0.6927 | 0.096* | 0.137 (4) |
C16Z | 1.227 (7) | 0.456 (5) | 0.742 (2) | 0.11 (2)* | 0.137 (4) |
H16J | 1.2873 | 0.3926 | 0.7354 | 0.166* | 0.137 (4) |
H16K | 1.3167 | 0.5079 | 0.7313 | 0.166* | 0.137 (4) |
H16L | 1.2128 | 0.4631 | 0.7707 | 0.166* | 0.137 (4) |
C17Z | 0.891 (10) | 0.554 (3) | 0.726 (2) | 0.08 (2)* | 0.137 (4) |
H17J | 0.7620 | 0.5453 | 0.7117 | 0.120* | 0.137 (4) |
H17K | 0.8610 | 0.5654 | 0.7548 | 0.120* | 0.137 (4) |
H17L | 0.9648 | 0.6102 | 0.7154 | 0.120* | 0.137 (4) |
C18Z | 0.613 (10) | 0.252 (5) | 0.8202 (13) | 0.088 (15)* | 0.137 (4) |
H18Z | 0.6577 | 0.1850 | 0.8282 | 0.105* | 0.137 (4) |
C19Z | 0.750 (11) | 0.322 (6) | 0.8437 (17) | 0.12 (2)* | 0.137 (4) |
H19J | 0.7123 | 0.3205 | 0.8721 | 0.178* | 0.137 (4) |
H19K | 0.8934 | 0.3033 | 0.8405 | 0.178* | 0.137 (4) |
H19L | 0.7305 | 0.3887 | 0.8334 | 0.178* | 0.137 (4) |
C20Z | 0.383 (11) | 0.259 (10) | 0.831 (3) | 0.10 (3)* | 0.137 (4) |
H20J | 0.3051 | 0.2120 | 0.8150 | 0.143* | 0.137 (4) |
H20K | 0.3643 | 0.2443 | 0.8596 | 0.143* | 0.137 (4) |
H20L | 0.3331 | 0.3249 | 0.8255 | 0.143* | 0.137 (4) |
C21Z | 0.767 (7) | 0.183 (3) | 0.6647 (10) | 0.091 (14)* | 0.137 (4) |
C22Z | 0.906 (9) | 0.091 (3) | 0.6633 (18) | 0.087 (19)* | 0.137 (4) |
H22I | 0.9151 | 0.0673 | 0.6356 | 0.131* | 0.137 (4) |
H22J | 1.0432 | 0.1076 | 0.6730 | 0.131* | 0.137 (4) |
H22K | 0.8472 | 0.0399 | 0.6803 | 0.131* | 0.137 (4) |
C23Z | 0.570 (9) | 0.169 (5) | 0.639 (2) | 0.15 (3)* | 0.137 (4) |
H23J | 0.6069 | 0.1458 | 0.6124 | 0.221* | 0.137 (4) |
H23K | 0.4797 | 0.1213 | 0.6521 | 0.221* | 0.137 (4) |
H23L | 0.4977 | 0.2315 | 0.6369 | 0.221* | 0.137 (4) |
N1 | 0.0664 (9) | 0.6673 (4) | 0.49238 (17) | 0.070 (2) | |
H1A | 0.1673 | 0.6448 | 0.5087 | 0.084* | |
H1B | −0.0577 | 0.6521 | 0.5030 | 0.084* | |
H1C | 0.0775 | 0.7330 | 0.4900 | 0.084* | |
C24 | 0.3019 (16) | 0.6494 (7) | 0.4333 (3) | 0.111 (4) | |
H24A | 0.4094 | 0.6319 | 0.4525 | 0.167* | |
H24B | 0.3049 | 0.7199 | 0.4286 | 0.167* | |
H24C | 0.3255 | 0.6151 | 0.4080 | 0.167* | |
C25 | 0.0869 (15) | 0.6197 (7) | 0.4507 (2) | 0.079 (3) | |
H25 | −0.0216 | 0.6475 | 0.4329 | 0.094* | |
C26 | 0.054 (2) | 0.5098 (9) | 0.4535 (3) | 0.095 (3) | |
C27 | −0.136 (2) | 0.4703 (11) | 0.4397 (3) | 0.116 (4) | |
H27 | −0.2407 | 0.5121 | 0.4300 | 0.139* | |
C28 | −0.166 (3) | 0.3671 (15) | 0.4407 (5) | 0.159 (6) | |
H28 | −0.2907 | 0.3389 | 0.4317 | 0.191* | |
C29 | −0.009 (5) | 0.3094 (17) | 0.4552 (7) | 0.205 (13) | |
H29 | −0.0262 | 0.2407 | 0.4547 | 0.246* | |
C30 | 0.171 (4) | 0.3460 (16) | 0.4703 (6) | 0.195 (9) | |
H30 | 0.2720 | 0.3043 | 0.4815 | 0.234* | |
C31 | 0.201 (2) | 0.4485 (11) | 0.4686 (3) | 0.133 (5) | |
H31 | 0.3258 | 0.4752 | 0.4782 | 0.160* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.083 (15) | 0.072 (17) | 0.082 (14) | 0.011 (14) | 0.018 (13) | 0.012 (13) |
O2 | 0.080 (4) | 0.107 (4) | 0.079 (4) | 0.005 (4) | 0.011 (3) | 0.034 (4) |
O3 | 0.076 (4) | 0.146 (5) | 0.070 (4) | 0.029 (5) | 0.007 (4) | 0.031 (4) |
C14 | 0.099 (7) | 0.072 (5) | 0.049 (5) | 0.012 (5) | −0.005 (6) | 0.004 (4) |
O1D | 0.073 (11) | 0.075 (17) | 0.085 (14) | 0.010 (13) | 0.020 (11) | −0.001 (13) |
O2D | 0.080 (4) | 0.107 (4) | 0.079 (4) | 0.005 (4) | 0.011 (3) | 0.034 (4) |
O3D | 0.076 (4) | 0.146 (5) | 0.070 (4) | 0.029 (5) | 0.007 (4) | 0.031 (4) |
C14D | 0.099 (7) | 0.072 (5) | 0.049 (5) | 0.012 (5) | −0.005 (6) | 0.004 (4) |
O1P | 0.073 (14) | 0.076 (18) | 0.075 (16) | 0.007 (14) | 0.019 (14) | 0.011 (14) |
O2P | 0.080 (4) | 0.107 (4) | 0.079 (4) | 0.005 (4) | 0.011 (3) | 0.034 (4) |
O3P | 0.076 (4) | 0.146 (5) | 0.070 (4) | 0.029 (5) | 0.007 (4) | 0.031 (4) |
C14P | 0.099 (7) | 0.072 (5) | 0.049 (5) | 0.012 (5) | −0.005 (6) | 0.004 (4) |
O2Z | 0.080 (4) | 0.107 (4) | 0.079 (4) | 0.005 (4) | 0.011 (3) | 0.034 (4) |
O3Z | 0.076 (4) | 0.146 (5) | 0.070 (4) | 0.029 (5) | 0.007 (4) | 0.031 (4) |
C14Z | 0.099 (7) | 0.072 (5) | 0.049 (5) | 0.012 (5) | −0.005 (6) | 0.004 (4) |
N1 | 0.061 (5) | 0.094 (5) | 0.056 (4) | 0.005 (4) | 0.003 (4) | 0.012 (4) |
C24 | 0.116 (9) | 0.141 (9) | 0.077 (6) | −0.006 (8) | 0.025 (6) | 0.005 (6) |
C25 | 0.076 (7) | 0.102 (8) | 0.058 (6) | 0.017 (6) | −0.014 (5) | 0.006 (5) |
C26 | 0.120 (11) | 0.112 (10) | 0.053 (6) | 0.011 (10) | −0.003 (7) | −0.005 (6) |
C27 | 0.108 (11) | 0.138 (12) | 0.101 (9) | −0.007 (9) | 0.018 (8) | −0.011 (8) |
C28 | 0.174 (18) | 0.143 (16) | 0.160 (15) | −0.062 (14) | 0.030 (13) | −0.037 (12) |
C29 | 0.34 (4) | 0.122 (17) | 0.157 (18) | −0.02 (2) | 0.03 (2) | −0.015 (13) |
C30 | 0.29 (3) | 0.134 (19) | 0.161 (16) | 0.052 (17) | −0.034 (16) | 0.008 (12) |
C31 | 0.176 (15) | 0.105 (10) | 0.118 (10) | 0.016 (11) | −0.033 (10) | 0.005 (8) |
O1—C7 | 1.21 (2) | C3P—H3P | 0.9506 |
O2—C14 | 1.266 (9) | C4P—C5P | 1.3902 |
O3—C14 | 1.225 (9) | C4P—C18P | 1.52 (2) |
C1—C6 | 1.39 (2) | C5P—H5P | 0.9502 |
C1—C2 | 1.40 (2) | C7P—C8P | 1.533 (19) |
C1—C7 | 1.52 (2) | C7P—C15P | 1.65 (2) |
C6—C5 | 1.39 (2) | C8P—C13P | 1.3902 |
C6—C21 | 1.52 (2) | C8P—C9P | 1.3909 |
C5—C4 | 1.38 (2) | C9P—C10P | 1.3882 |
C5—H5 | 0.9300 | C9P—H9P | 0.9497 |
C4—C3 | 1.38 (2) | C10P—C11P | 1.3908 |
C4—C18 | 1.53 (2) | C10P—H10P | 0.9502 |
C3—C2 | 1.40 (2) | C11P—C12P | 1.3877 |
C3—H3 | 0.9300 | C11P—C14P | 1.519 (15) |
C2—C15 | 1.51 (2) | C12P—C13P | 1.3906 |
C7—C8 | 1.50 (2) | C12P—H12P | 0.9499 |
C8—C9 | 1.36 (2) | C13P—H13P | 0.9501 |
C8—C13 | 1.37 (2) | C15P—C16P | 1.51 (2) |
C13—C12 | 1.39 (2) | C15P—C17P | 1.53 (2) |
C13—H13 | 0.9300 | C16P—H16G | 0.9600 |
C9—C10 | 1.39 (2) | C16P—H16H | 0.9600 |
C9—H9 | 0.9300 | C16P—H16I | 0.9600 |
C10—C11 | 1.37 (2) | C17P—H17G | 0.9600 |
C10—H10 | 0.9300 | C17P—H17H | 0.9600 |
C11—C12 | 1.39 (2) | C17P—H17I | 0.9600 |
C11—C14 | 1.52 (2) | C18P—C19P | 1.51 (3) |
C12—H12 | 0.9300 | C18P—C20P | 1.54 (3) |
C15—C16 | 1.50 (2) | C18P—H18P | 0.9800 |
C15—C17 | 1.50 (2) | C19P—H19G | 0.9600 |
C15—H15 | 0.9800 | C19P—H19H | 0.9600 |
C16—H16A | 0.9600 | C19P—H19I | 0.9600 |
C16—H16B | 0.9600 | C20P—H20G | 0.9600 |
C16—H16C | 0.9600 | C20P—H20H | 0.9600 |
C17—H17A | 0.9600 | C20P—H20I | 0.9600 |
C17—H17B | 0.9600 | C21P—C23P | 1.53 (3) |
C17—H17C | 0.9600 | C21P—C22P | 1.54 (3) |
C18—C19 | 1.47 (2) | C21P—H21P | 0.9800 |
C18—C20 | 1.50 (2) | C22P—H22F | 0.9600 |
C18—H18 | 0.9800 | C22P—H22G | 0.9600 |
C19—H19A | 0.9600 | C22P—H22H | 0.9600 |
C19—H19B | 0.9600 | C23P—H23G | 0.9600 |
C19—H19C | 0.9600 | C23P—H23H | 0.9600 |
C20—H20A | 0.9600 | C23P—H23I | 0.9600 |
C20—H20B | 0.9600 | O1Z—C7Z | 1.42 (3) |
C20—H20C | 0.9600 | O2Z—C14Z | 1.266 (9) |
C21—C22 | 1.53 (3) | O3Z—C14Z | 1.225 (9) |
C21—C23 | 1.57 (2) | C6Z—C5Z | 1.3894 |
C21—H21 | 0.9800 | C6Z—C1Z | 1.3922 |
C22—H22A | 0.9600 | C6Z—C21Z | 1.51 (2) |
C22—H22B | 0.9600 | C1Z—C2Z | 1.3891 |
C22—H22C | 0.9600 | C1Z—C7Z | 1.52 (2) |
C23—H23A | 0.9600 | C2Z—C3Z | 1.3894 |
C23—H23B | 0.9600 | C2Z—C15Z | 1.49 (2) |
C23—H23C | 0.9600 | C3Z—C4Z | 1.3887 |
O1D—C7D | 1.46 (2) | C3Z—H3Z | 0.9503 |
O2D—C14D | 1.266 (9) | C4Z—C5Z | 1.3901 |
O3D—C14D | 1.225 (9) | C4Z—C18Z | 1.50 (2) |
C1D—C2D | 1.362 (19) | C5Z—H5Z | 0.9508 |
C1D—C6D | 1.379 (19) | C7Z—C8Z | 1.55 (2) |
C1D—C7D | 1.569 (19) | C7Z—C21Z | 1.64 (2) |
C2D—C3D | 1.41 (2) | C8Z—C13Z | 1.3906 |
C2D—C15D | 1.52 (2) | C8Z—C9Z | 1.3919 |
C3D—C4D | 1.42 (2) | C9Z—C10Z | 1.3876 |
C3D—H3D | 0.9300 | C9Z—H9Z | 0.9484 |
C4D—C5D | 1.41 (2) | C10Z—C11Z | 1.3919 |
C4D—C18D | 1.59 (2) | C10Z—H10Z | 0.9502 |
C5D—C6D | 1.384 (19) | C11Z—C12Z | 1.3870 |
C5D—H5D | 0.9300 | C11Z—C14Z | 1.564 (18) |
C6D—C21D | 1.53 (2) | C12Z—C13Z | 1.3948 |
C7D—C22D | 1.50 (2) | C12Z—H12Z | 0.9481 |
C7D—C8D | 1.541 (18) | C13Z—H13Z | 0.9480 |
C9D—C10D | 1.376 (18) | C15Z—C17Z | 1.47 (3) |
C9D—C8D | 1.387 (18) | C15Z—C16Z | 1.47 (3) |
C9D—H9D | 0.9300 | C15Z—H15Z | 0.9800 |
C8D—C13D | 1.358 (19) | C16Z—H16J | 0.9600 |
C13D—C12D | 1.396 (19) | C16Z—H16K | 0.9600 |
C13D—H13D | 0.9300 | C16Z—H16L | 0.9600 |
C12D—C11D | 1.396 (19) | C17Z—H17J | 0.9600 |
C12D—H12D | 0.9300 | C17Z—H17K | 0.9600 |
C11D—C10D | 1.377 (19) | C17Z—H17L | 0.9600 |
C11D—C14D | 1.486 (16) | C18Z—C19Z | 1.50 (3) |
C10D—H10D | 0.9300 | C18Z—C20Z | 1.52 (3) |
C15D—C16D | 1.50 (2) | C18Z—H18Z | 0.9800 |
C15D—C17D | 1.55 (2) | C19Z—H19J | 0.9600 |
C15D—H15D | 0.9800 | C19Z—H19K | 0.9600 |
C16D—H16D | 0.9600 | C19Z—H19L | 0.9600 |
C16D—H16E | 0.9600 | C20Z—H20J | 0.9600 |
C16D—H16F | 0.9600 | C20Z—H20K | 0.9600 |
C17D—H17D | 0.9600 | C20Z—H20L | 0.9600 |
C17D—H17E | 0.9600 | C21Z—C22Z | 1.52 (2) |
C17D—H17F | 0.9600 | C21Z—C23Z | 1.52 (2) |
C18D—C19D | 1.49 (2) | C22Z—H22I | 0.9600 |
C18D—C20D | 1.52 (2) | C22Z—H22J | 0.9600 |
C18D—H18D | 0.9800 | C22Z—H22K | 0.9600 |
C19D—H19D | 0.9600 | C23Z—H23J | 0.9600 |
C19D—H19E | 0.9600 | C23Z—H23K | 0.9600 |
C19D—H19F | 0.9600 | C23Z—H23L | 0.9600 |
C20D—H20D | 0.9600 | N1—C25 | 1.510 (9) |
C20D—H20E | 0.9600 | N1—H1A | 0.8900 |
C20D—H20F | 0.9600 | N1—H1B | 0.8900 |
C21D—C23D | 1.48 (2) | N1—H1C | 0.8900 |
C21D—C22D | 1.55 (2) | C24—C25 | 1.540 (12) |
C21D—H21D | 0.9800 | C24—H24A | 0.9600 |
C22D—H22D | 0.9700 | C24—H24B | 0.9600 |
C22D—H22E | 0.9700 | C24—H24C | 0.9600 |
C23D—H23D | 0.9600 | C25—C26 | 1.495 (13) |
C23D—H23E | 0.9600 | C25—H25 | 0.9800 |
C23D—H23F | 0.9600 | C26—C31 | 1.344 (15) |
O1P—C7P | 1.41 (2) | C26—C27 | 1.399 (15) |
O2P—C14P | 1.266 (9) | C27—C28 | 1.402 (17) |
O3P—C14P | 1.225 (9) | C27—H27 | 0.9300 |
C6P—C1P | 1.3892 | C28—C29 | 1.36 (2) |
C6P—C5P | 1.3911 | C28—H28 | 0.9300 |
C6P—C21P | 1.51 (2) | C29—C30 | 1.34 (2) |
C1P—C2P | 1.3907 | C29—H29 | 0.9300 |
C1P—C7P | 1.51 (2) | C30—C31 | 1.393 (19) |
C2P—C3P | 1.3909 | C30—H30 | 0.9300 |
C2P—C15P | 1.50 (2) | C31—H31 | 0.9300 |
C3P—C4P | 1.3861 | ||
C6—C1—C2 | 121 (2) | C1P—C7P—C8P | 118 (2) |
C6—C1—C7 | 114 (2) | O1P—C7P—C15P | 116 (3) |
C2—C1—C7 | 125 (2) | C1P—C7P—C15P | 84.1 (15) |
C1—C6—C5 | 118 (2) | C8P—C7P—C15P | 108.9 (17) |
C1—C6—C21 | 121 (2) | C13P—C8P—C9P | 119.9 |
C5—C6—C21 | 121 (2) | C13P—C8P—C7P | 120.6 (17) |
C4—C5—C6 | 123 (3) | C9P—C8P—C7P | 119.4 (17) |
C4—C5—H5 | 118.7 | C10P—C9P—C8P | 120.0 |
C6—C5—H5 | 118.7 | C10P—C9P—H9P | 120.1 |
C5—C4—C3 | 119 (2) | C8P—C9P—H9P | 119.9 |
C5—C4—C18 | 125 (3) | C9P—C10P—C11P | 120.1 |
C3—C4—C18 | 116 (2) | C9P—C10P—H10P | 119.9 |
C4—C3—C2 | 120 (3) | C11P—C10P—H10P | 120.0 |
C4—C3—H3 | 119.8 | C12P—C11P—C10P | 120.0 |
C2—C3—H3 | 119.8 | C12P—C11P—C14P | 117.7 (18) |
C1—C2—C3 | 120 (2) | C10P—C11P—C14P | 122.3 (18) |
C1—C2—C15 | 120 (2) | C11P—C12P—C13P | 120.0 |
C3—C2—C15 | 120 (2) | C11P—C12P—H12P | 120.1 |
O1—C7—C8 | 119 (3) | C13P—C12P—H12P | 119.9 |
O1—C7—C1 | 124 (3) | C8P—C13P—C12P | 120.0 |
C8—C7—C1 | 117 (2) | C8P—C13P—H13P | 120.0 |
C9—C8—C13 | 117 (2) | C12P—C13P—H13P | 120.0 |
C9—C8—C7 | 119 (2) | O3P—C14P—O2P | 123.4 (7) |
C13—C8—C7 | 123 (2) | O3P—C14P—C11P | 119.6 (14) |
C8—C13—C12 | 124 (3) | O2P—C14P—C11P | 116.0 (14) |
C8—C13—H13 | 118.2 | C2P—C15P—C16P | 120 (3) |
C12—C13—H13 | 118.2 | C2P—C15P—C17P | 118 (3) |
C8—C9—C10 | 121 (3) | C16P—C15P—C17P | 108 (3) |
C8—C9—H9 | 119.7 | C2P—C15P—C7P | 85.6 (16) |
C10—C9—H9 | 119.7 | C16P—C15P—C7P | 112 (3) |
C11—C10—C9 | 123 (3) | C17P—C15P—C7P | 112 (3) |
C11—C10—H10 | 118.7 | C15P—C16P—H16G | 109.5 |
C9—C10—H10 | 118.7 | C15P—C16P—H16H | 109.5 |
C10—C11—C12 | 117 (2) | H16G—C16P—H16H | 109.5 |
C10—C11—C14 | 123 (2) | C15P—C16P—H16I | 109.5 |
C12—C11—C14 | 119 (2) | H16G—C16P—H16I | 109.5 |
C13—C12—C11 | 119 (3) | H16H—C16P—H16I | 109.5 |
C13—C12—H12 | 120.6 | C15P—C17P—H17G | 109.5 |
C11—C12—H12 | 120.6 | C15P—C17P—H17H | 109.5 |
O3—C14—O2 | 123.4 (7) | H17G—C17P—H17H | 109.5 |
O3—C14—C11 | 120.1 (16) | C15P—C17P—H17I | 109.5 |
O2—C14—C11 | 116.4 (16) | H17G—C17P—H17I | 109.5 |
C16—C15—C17 | 113 (3) | H17H—C17P—H17I | 109.5 |
C16—C15—C2 | 117 (3) | C19P—C18P—C4P | 111 (3) |
C17—C15—C2 | 116 (3) | C19P—C18P—C20P | 111 (3) |
C16—C15—H15 | 102.5 | C4P—C18P—C20P | 98 (3) |
C17—C15—H15 | 102.5 | C19P—C18P—H18P | 112.1 |
C2—C15—H15 | 102.5 | C4P—C18P—H18P | 112.1 |
C15—C16—H16A | 109.5 | C20P—C18P—H18P | 112.1 |
C15—C16—H16B | 109.5 | C18P—C19P—H19G | 109.5 |
H16A—C16—H16B | 109.5 | C18P—C19P—H19H | 109.5 |
C15—C16—H16C | 109.5 | H19G—C19P—H19H | 109.5 |
H16A—C16—H16C | 109.5 | C18P—C19P—H19I | 109.5 |
H16B—C16—H16C | 109.5 | H19G—C19P—H19I | 109.5 |
C15—C17—H17A | 109.5 | H19H—C19P—H19I | 109.5 |
C15—C17—H17B | 109.5 | C18P—C20P—H20G | 109.5 |
H17A—C17—H17B | 109.5 | C18P—C20P—H20H | 109.5 |
C15—C17—H17C | 109.5 | H20G—C20P—H20H | 109.5 |
H17A—C17—H17C | 109.5 | C18P—C20P—H20I | 109.5 |
H17B—C17—H17C | 109.5 | H20G—C20P—H20I | 109.5 |
C19—C18—C20 | 115 (3) | H20H—C20P—H20I | 109.5 |
C19—C18—C4 | 121 (3) | C6P—C21P—C23P | 116 (3) |
C20—C18—C4 | 112 (2) | C6P—C21P—C22P | 110 (3) |
C19—C18—H18 | 101.5 | C23P—C21P—C22P | 107 (3) |
C20—C18—H18 | 101.5 | C6P—C21P—H21P | 107.6 |
C4—C18—H18 | 101.5 | C23P—C21P—H21P | 107.6 |
C18—C19—H19A | 109.5 | C22P—C21P—H21P | 107.7 |
C18—C19—H19B | 109.5 | C21P—C22P—H22F | 109.5 |
H19A—C19—H19B | 109.5 | C21P—C22P—H22G | 109.5 |
C18—C19—H19C | 109.5 | H22F—C22P—H22G | 109.5 |
H19A—C19—H19C | 109.5 | C21P—C22P—H22H | 109.5 |
H19B—C19—H19C | 109.5 | H22F—C22P—H22H | 109.5 |
C18—C20—H20A | 109.5 | H22G—C22P—H22H | 109.5 |
C18—C20—H20B | 109.5 | C21P—C23P—H23G | 109.5 |
H20A—C20—H20B | 109.5 | C21P—C23P—H23H | 109.5 |
C18—C20—H20C | 109.5 | H23G—C23P—H23H | 109.5 |
H20A—C20—H20C | 109.5 | C21P—C23P—H23I | 109.5 |
H20B—C20—H20C | 109.5 | H23G—C23P—H23I | 109.5 |
C6—C21—C22 | 109 (3) | H23H—C23P—H23I | 109.5 |
C6—C21—C23 | 110 (3) | C5Z—C6Z—C1Z | 120.0 |
C22—C21—C23 | 106 (3) | C5Z—C6Z—C21Z | 145.4 (18) |
C6—C21—H21 | 110.4 | C1Z—C6Z—C21Z | 94.5 (17) |
C22—C21—H21 | 110.4 | C2Z—C1Z—C6Z | 119.8 |
C23—C21—H21 | 110.4 | C2Z—C1Z—C7Z | 144.5 (17) |
C21—C22—H22A | 109.5 | C6Z—C1Z—C7Z | 94.8 (17) |
C21—C22—H22B | 109.5 | C1Z—C2Z—C3Z | 120.20 (8) |
H22A—C22—H22B | 109.5 | C1Z—C2Z—C15Z | 117 (2) |
C21—C22—H22C | 109.5 | C3Z—C2Z—C15Z | 123 (2) |
H22A—C22—H22C | 109.5 | C4Z—C3Z—C2Z | 119.9 |
H22B—C22—H22C | 109.5 | C4Z—C3Z—H3Z | 120.0 |
C21—C23—H23A | 109.5 | C2Z—C3Z—H3Z | 120.0 |
C21—C23—H23B | 109.5 | C3Z—C4Z—C5Z | 120.0 |
H23A—C23—H23B | 109.5 | C3Z—C4Z—C18Z | 119 (2) |
C21—C23—H23C | 109.5 | C5Z—C4Z—C18Z | 121 (2) |
H23A—C23—H23C | 109.5 | C6Z—C5Z—C4Z | 120.06 (7) |
H23B—C23—H23C | 109.5 | C6Z—C5Z—H5Z | 120.0 |
C2D—C1D—C6D | 120.9 (17) | C4Z—C5Z—H5Z | 120.0 |
C2D—C1D—C7D | 125.7 (18) | O1Z—C7Z—C1Z | 95 (3) |
C6D—C1D—C7D | 113.0 (16) | O1Z—C7Z—C8Z | 114 (3) |
C1D—C2D—C3D | 119.5 (18) | C1Z—C7Z—C8Z | 119 (3) |
C1D—C2D—C15D | 121.6 (19) | O1Z—C7Z—C21Z | 115 (3) |
C3D—C2D—C15D | 118.8 (19) | C1Z—C7Z—C21Z | 84.7 (17) |
C2D—C3D—C4D | 121.1 (19) | C8Z—C7Z—C21Z | 122 (2) |
C2D—C3D—H3D | 119.5 | C13Z—C8Z—C9Z | 120.1 |
C4D—C3D—H3D | 119.5 | C13Z—C8Z—C7Z | 120 (2) |
C5D—C4D—C3D | 116.5 (18) | C9Z—C8Z—C7Z | 120 (2) |
C5D—C4D—C18D | 112.5 (19) | C10Z—C9Z—C8Z | 120.0 |
C3D—C4D—C18D | 130 (2) | C10Z—C9Z—H9Z | 119.8 |
C6D—C5D—C4D | 122 (2) | C8Z—C9Z—H9Z | 120.2 |
C6D—C5D—H5D | 119.2 | C9Z—C10Z—C11Z | 119.9 |
C4D—C5D—H5D | 119.2 | C9Z—C10Z—H10Z | 120.4 |
C1D—C6D—C5D | 120.3 (18) | C11Z—C10Z—H10Z | 119.8 |
C1D—C6D—C21D | 108.2 (16) | C12Z—C11Z—C10Z | 120.4 |
C5D—C6D—C21D | 131.5 (19) | C12Z—C11Z—C14Z | 118 (2) |
O1D—C7D—C22D | 109.8 (18) | C10Z—C11Z—C14Z | 122 (2) |
O1D—C7D—C8D | 109.0 (18) | C11Z—C12Z—C13Z | 119.8 |
C22D—C7D—C8D | 114.2 (18) | C11Z—C12Z—H12Z | 120.5 |
O1D—C7D—C1D | 110.5 (19) | C13Z—C12Z—H12Z | 119.8 |
C22D—C7D—C1D | 99.6 (14) | C8Z—C13Z—C12Z | 119.9 |
C8D—C7D—C1D | 113.4 (18) | C8Z—C13Z—H13Z | 120.1 |
C10D—C9D—C8D | 118.8 (19) | C12Z—C13Z—H13Z | 120.0 |
C10D—C9D—H9D | 120.6 | O3Z—C14Z—O2Z | 123.4 (7) |
C8D—C9D—H9D | 120.6 | O3Z—C14Z—C11Z | 118.3 (14) |
C13D—C8D—C9D | 120.0 (17) | O2Z—C14Z—C11Z | 118.3 (14) |
C13D—C8D—C7D | 120.1 (17) | C17Z—C15Z—C16Z | 122 (4) |
C9D—C8D—C7D | 119.9 (17) | C17Z—C15Z—C2Z | 112 (3) |
C8D—C13D—C12D | 121 (2) | C16Z—C15Z—C2Z | 107 (3) |
C8D—C13D—H13D | 119.4 | C17Z—C15Z—H15Z | 104.8 |
C12D—C13D—H13D | 119.4 | C16Z—C15Z—H15Z | 104.8 |
C13D—C12D—C11D | 120 (2) | C2Z—C15Z—H15Z | 104.8 |
C13D—C12D—H12D | 120.2 | C15Z—C16Z—H16J | 109.5 |
C11D—C12D—H12D | 120.2 | C15Z—C16Z—H16K | 109.5 |
C10D—C11D—C12D | 117.8 (17) | H16J—C16Z—H16K | 109.5 |
C10D—C11D—C14D | 121.0 (17) | C15Z—C16Z—H16L | 109.5 |
C12D—C11D—C14D | 121.2 (17) | H16J—C16Z—H16L | 109.5 |
C9D—C10D—C11D | 123 (2) | H16K—C16Z—H16L | 109.5 |
C9D—C10D—H10D | 118.6 | C15Z—C17Z—H17J | 109.5 |
C11D—C10D—H10D | 118.6 | C15Z—C17Z—H17K | 109.5 |
O3D—C14D—O2D | 123.4 (7) | H17J—C17Z—H17K | 109.5 |
O3D—C14D—C11D | 117.0 (12) | C15Z—C17Z—H17L | 109.5 |
O2D—C14D—C11D | 119.5 (12) | H17J—C17Z—H17L | 109.5 |
C16D—C15D—C2D | 108 (2) | H17K—C17Z—H17L | 109.5 |
C16D—C15D—C17D | 114 (2) | C19Z—C18Z—C4Z | 98 (3) |
C2D—C15D—C17D | 107 (2) | C19Z—C18Z—C20Z | 114 (4) |
C16D—C15D—H15D | 108.9 | C4Z—C18Z—C20Z | 125 (4) |
C2D—C15D—H15D | 108.9 | C19Z—C18Z—H18Z | 106.0 |
C17D—C15D—H15D | 108.9 | C4Z—C18Z—H18Z | 106.0 |
C15D—C16D—H16D | 109.5 | C20Z—C18Z—H18Z | 106.0 |
C15D—C16D—H16E | 109.5 | C18Z—C19Z—H19J | 109.5 |
H16D—C16D—H16E | 109.5 | C18Z—C19Z—H19K | 109.5 |
C15D—C16D—H16F | 109.5 | H19J—C19Z—H19K | 109.5 |
H16D—C16D—H16F | 109.5 | C18Z—C19Z—H19L | 109.5 |
H16E—C16D—H16F | 109.5 | H19J—C19Z—H19L | 109.5 |
C15D—C17D—H17D | 109.5 | H19K—C19Z—H19L | 109.5 |
C15D—C17D—H17E | 109.5 | C18Z—C20Z—H20J | 109.5 |
H17D—C17D—H17E | 109.5 | C18Z—C20Z—H20K | 109.5 |
C15D—C17D—H17F | 109.5 | H20J—C20Z—H20K | 109.5 |
H17D—C17D—H17F | 109.5 | C18Z—C20Z—H20L | 109.5 |
H17E—C17D—H17F | 109.5 | H20J—C20Z—H20L | 109.5 |
C19D—C18D—C20D | 117 (2) | H20K—C20Z—H20L | 109.5 |
C19D—C18D—C4D | 112.5 (19) | C6Z—C21Z—C22Z | 109 (3) |
C20D—C18D—C4D | 112 (2) | C6Z—C21Z—C23Z | 121 (3) |
C19D—C18D—H18D | 104.3 | C22Z—C21Z—C23Z | 112 (3) |
C20D—C18D—H18D | 104.3 | C6Z—C21Z—C7Z | 85.6 (17) |
C4D—C18D—H18D | 104.3 | C22Z—C21Z—C7Z | 115 (3) |
C18D—C19D—H19D | 109.5 | C23Z—C21Z—C7Z | 113 (3) |
C18D—C19D—H19E | 109.5 | C21Z—C22Z—H22I | 109.5 |
H19D—C19D—H19E | 109.5 | C21Z—C22Z—H22J | 109.5 |
C18D—C19D—H19F | 109.5 | H22I—C22Z—H22J | 109.5 |
H19D—C19D—H19F | 109.5 | C21Z—C22Z—H22K | 109.5 |
H19E—C19D—H19F | 109.5 | H22I—C22Z—H22K | 109.5 |
C18D—C20D—H20D | 109.5 | H22J—C22Z—H22K | 109.5 |
C18D—C20D—H20E | 109.5 | C21Z—C23Z—H23J | 109.5 |
H20D—C20D—H20E | 109.5 | C21Z—C23Z—H23K | 109.5 |
C18D—C20D—H20F | 109.5 | H23J—C23Z—H23K | 109.5 |
H20D—C20D—H20F | 109.5 | C21Z—C23Z—H23L | 109.5 |
H20E—C20D—H20F | 109.5 | H23J—C23Z—H23L | 109.5 |
C23D—C21D—C6D | 118 (2) | H23K—C23Z—H23L | 109.5 |
C23D—C21D—C22D | 116 (2) | C25—N1—H1A | 109.5 |
C6D—C21D—C22D | 101.7 (17) | C25—N1—H1B | 109.5 |
C23D—C21D—H21D | 106.9 | H1A—N1—H1B | 109.5 |
C6D—C21D—H21D | 106.9 | C25—N1—H1C | 109.5 |
C22D—C21D—H21D | 106.9 | H1A—N1—H1C | 109.5 |
C7D—C22D—C21D | 108.7 (16) | H1B—N1—H1C | 109.5 |
C7D—C22D—H22D | 109.9 | C25—C24—H24A | 109.5 |
C21D—C22D—H22D | 109.9 | C25—C24—H24B | 109.5 |
C7D—C22D—H22E | 109.9 | H24A—C24—H24B | 109.5 |
C21D—C22D—H22E | 109.9 | C25—C24—H24C | 109.5 |
H22D—C22D—H22E | 108.3 | H24A—C24—H24C | 109.5 |
C21D—C23D—H23D | 109.5 | H24B—C24—H24C | 109.5 |
C21D—C23D—H23E | 109.5 | C26—C25—N1 | 110.6 (7) |
H23D—C23D—H23E | 109.5 | C26—C25—C24 | 113.9 (9) |
C21D—C23D—H23F | 109.5 | N1—C25—C24 | 107.5 (7) |
H23D—C23D—H23F | 109.5 | C26—C25—H25 | 108.2 |
H23E—C23D—H23F | 109.5 | N1—C25—H25 | 108.2 |
C1P—C6P—C5P | 120.0 | C24—C25—H25 | 108.2 |
C1P—C6P—C21P | 125 (2) | C31—C26—C27 | 119.5 (12) |
C5P—C6P—C21P | 115 (2) | C31—C26—C25 | 122.0 (13) |
C6P—C1P—C2P | 120.0 | C27—C26—C25 | 118.5 (12) |
C6P—C1P—C7P | 144.1 (17) | C26—C27—C28 | 119.2 (14) |
C2P—C1P—C7P | 95.4 (16) | C26—C27—H27 | 120.4 |
C1P—C2P—C3P | 119.90 (7) | C28—C27—H27 | 120.4 |
C1P—C2P—C15P | 94.0 (17) | C29—C28—C27 | 118 (2) |
C3P—C2P—C15P | 146.0 (17) | C29—C28—H28 | 120.9 |
C4P—C3P—C2P | 120.1 | C27—C28—H28 | 120.9 |
C4P—C3P—H3P | 120.1 | C30—C29—C28 | 124 (3) |
C2P—C3P—H3P | 119.8 | C30—C29—H29 | 118.2 |
C3P—C4P—C5P | 120.1 | C28—C29—H29 | 118.2 |
C3P—C4P—C18P | 121 (2) | C29—C30—C31 | 118 (2) |
C5P—C4P—C18P | 119 (2) | C29—C30—H30 | 121.1 |
C4P—C5P—C6P | 119.92 (7) | C31—C30—H30 | 121.1 |
C4P—C5P—H5P | 120.1 | C26—C31—C30 | 121.7 (17) |
C6P—C5P—H5P | 120.0 | C26—C31—H31 | 119.1 |
O1P—C7P—C1P | 122 (3) | C30—C31—H31 | 119.1 |
O1P—C7P—C8P | 106 (2) |
C31H39NO3 | Dx = 1.126 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 1033 reflections |
a = 6.401 (2) Å | θ = 1.6–16.7° |
b = 13.422 (4) Å | µ = 0.07 mm−1 |
c = 32.510 (9) Å | T = 299 K |
V = 2793.1 (14) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.12 × 0.10 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 5392 independent reflections |
Radiation source: fine-focus sealed tube | 1731 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.138 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −14→16 |
Tmin = 0.413, Tmax = 1.000 | l = −40→40 |
24981 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.092 | H-atom parameters constrained |
wR(F2) = 0.247 | w = 1/[σ2(Fo2) + (0.0665P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
5392 reflections | Δρmax = 0.14 e Å−3 |
402 parameters | Δρmin = −0.15 e Å−3 |
494 restraints | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −1.0 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 1.062 (7) | 0.243 (4) | 0.6402 (18) | 0.084 (10) | 0.209 (4) |
O2 | 0.6682 (10) | 0.6314 (4) | 0.51864 (18) | 0.094 (2) | 0.209 (4) |
O3 | 0.3655 (11) | 0.6146 (5) | 0.54890 (18) | 0.102 (2) | 0.209 (4) |
C6 | 0.697 (7) | 0.197 (2) | 0.6997 (8) | 0.068 (11)* | 0.209 (4) |
C1 | 0.826 (7) | 0.280 (3) | 0.6946 (8) | 0.070 (13)* | 0.209 (4) |
C2 | 0.864 (7) | 0.345 (3) | 0.7271 (9) | 0.074 (12)* | 0.209 (4) |
C3 | 0.771 (6) | 0.325 (3) | 0.7649 (8) | 0.066 (10)* | 0.209 (4) |
H3 | 0.7944 | 0.3686 | 0.7867 | 0.079* | 0.209 (4) |
C4 | 0.645 (6) | 0.244 (3) | 0.7710 (7) | 0.063 (10)* | 0.209 (4) |
C5 | 0.609 (6) | 0.182 (2) | 0.7379 (9) | 0.079 (12)* | 0.209 (4) |
H5 | 0.5227 | 0.1269 | 0.7415 | 0.095* | 0.209 (4) |
C7 | 0.916 (5) | 0.294 (2) | 0.6521 (8) | 0.081 (12)* | 0.209 (4) |
C8 | 0.820 (5) | 0.3699 (17) | 0.6245 (7) | 0.059 (11)* | 0.209 (4) |
C9 | 0.940 (4) | 0.412 (2) | 0.5940 (9) | 0.041 (9)* | 0.209 (4) |
H9 | 1.0777 | 0.3931 | 0.5908 | 0.049* | 0.209 (4) |
C10 | 0.857 (5) | 0.483 (2) | 0.5682 (9) | 0.071 (12)* | 0.209 (4) |
H10 | 0.9400 | 0.5114 | 0.5481 | 0.085* | 0.209 (4) |
C11 | 0.652 (5) | 0.511 (3) | 0.5717 (12) | 0.064 (13)* | 0.209 (4) |
C12 | 0.531 (5) | 0.466 (4) | 0.6010 (15) | 0.071 (13)* | 0.209 (4) |
H12 | 0.3906 | 0.4826 | 0.6030 | 0.085* | 0.209 (4) |
C13 | 0.615 (5) | 0.397 (3) | 0.6275 (12) | 0.068 (12)* | 0.209 (4) |
H13 | 0.5318 | 0.3682 | 0.6476 | 0.082* | 0.209 (4) |
C14 | 0.5514 (16) | 0.5918 (6) | 0.5446 (3) | 0.078 (2) | 0.209 (4) |
C15 | 1.028 (6) | 0.428 (3) | 0.7224 (15) | 0.081 (12)* | 0.209 (4) |
H15 | 1.0429 | 0.4429 | 0.6930 | 0.098* | 0.209 (4) |
C16 | 1.239 (7) | 0.391 (4) | 0.738 (2) | 0.13 (2)* | 0.209 (4) |
H16A | 1.2773 | 0.3312 | 0.7242 | 0.194* | 0.209 (4) |
H16B | 1.3437 | 0.4413 | 0.7336 | 0.194* | 0.209 (4) |
H16C | 1.2295 | 0.3782 | 0.7673 | 0.194* | 0.209 (4) |
C17 | 0.960 (7) | 0.523 (3) | 0.7438 (15) | 0.094 (14)* | 0.209 (4) |
H17A | 0.8271 | 0.5442 | 0.7330 | 0.141* | 0.209 (4) |
H17B | 0.9474 | 0.5114 | 0.7728 | 0.141* | 0.209 (4) |
H17C | 1.0617 | 0.5745 | 0.7390 | 0.141* | 0.209 (4) |
C18 | 0.555 (6) | 0.221 (4) | 0.8140 (9) | 0.100 (13)* | 0.209 (4) |
H18 | 0.5359 | 0.1490 | 0.8155 | 0.119* | 0.209 (4) |
C19 | 0.694 (7) | 0.249 (4) | 0.8491 (11) | 0.067 (13)* | 0.209 (4) |
H19A | 0.8283 | 0.2183 | 0.8457 | 0.101* | 0.209 (4) |
H19B | 0.7114 | 0.3204 | 0.8497 | 0.101* | 0.209 (4) |
H19C | 0.6329 | 0.2275 | 0.8745 | 0.101* | 0.209 (4) |
C20 | 0.340 (6) | 0.267 (4) | 0.8168 (13) | 0.068 (14)* | 0.209 (4) |
H20A | 0.2583 | 0.2465 | 0.7936 | 0.102* | 0.209 (4) |
H20B | 0.2736 | 0.2453 | 0.8417 | 0.102* | 0.209 (4) |
H20C | 0.3521 | 0.3383 | 0.8170 | 0.102* | 0.209 (4) |
C21 | 0.643 (7) | 0.129 (3) | 0.6643 (12) | 0.084 (13)* | 0.209 (4) |
H21 | 0.6275 | 0.1661 | 0.6385 | 0.100* | 0.209 (4) |
C22 | 0.814 (8) | 0.049 (4) | 0.6610 (17) | 0.099 (17)* | 0.209 (4) |
H22A | 0.7818 | 0.0052 | 0.6387 | 0.148* | 0.209 (4) |
H22B | 0.9461 | 0.0809 | 0.6561 | 0.148* | 0.209 (4) |
H22C | 0.8201 | 0.0122 | 0.6862 | 0.148* | 0.209 (4) |
C23 | 0.440 (7) | 0.069 (4) | 0.675 (2) | 0.076 (15)* | 0.209 (4) |
H23A | 0.4055 | 0.0259 | 0.6528 | 0.114* | 0.209 (4) |
H23B | 0.4639 | 0.0307 | 0.6996 | 0.114* | 0.209 (4) |
H23C | 0.3275 | 0.1151 | 0.6799 | 0.114* | 0.209 (4) |
O1D | 1.099 (3) | 0.269 (2) | 0.6419 (10) | 0.081 (8) | 0.394 (4) |
O2D | 0.6682 (10) | 0.6314 (4) | 0.51864 (18) | 0.094 (2) | 0.394 (4) |
O3D | 0.3655 (11) | 0.6146 (5) | 0.54890 (18) | 0.102 (2) | 0.394 (4) |
C6D | 0.658 (4) | 0.2093 (14) | 0.7035 (5) | 0.070 (8)* | 0.394 (4) |
C1D | 0.807 (3) | 0.2794 (14) | 0.6921 (4) | 0.071 (8)* | 0.394 (4) |
C2D | 0.890 (3) | 0.3452 (13) | 0.7199 (5) | 0.072 (7)* | 0.394 (4) |
C3D | 0.834 (3) | 0.3351 (15) | 0.7614 (5) | 0.082 (7)* | 0.394 (4) |
H3D | 0.8927 | 0.3788 | 0.7811 | 0.098* | 0.394 (4) |
C4D | 0.690 (3) | 0.2612 (16) | 0.7747 (4) | 0.085 (9)* | 0.394 (4) |
C5D | 0.601 (3) | 0.2013 (14) | 0.7444 (6) | 0.068 (7)* | 0.394 (4) |
H5D | 0.4997 | 0.1536 | 0.7520 | 0.081* | 0.394 (4) |
C7D | 0.874 (3) | 0.2713 (14) | 0.6463 (6) | 0.083 (8)* | 0.394 (4) |
C8D | 0.783 (3) | 0.3558 (11) | 0.6206 (5) | 0.068 (8)* | 0.394 (4) |
C9D | 0.897 (3) | 0.3904 (15) | 0.5876 (6) | 0.070 (8)* | 0.394 (4) |
H9D | 1.0290 | 0.3618 | 0.5821 | 0.085* | 0.394 (4) |
C10D | 0.824 (3) | 0.4656 (17) | 0.5626 (6) | 0.072 (8)* | 0.394 (4) |
H10D | 0.9052 | 0.4878 | 0.5399 | 0.087* | 0.394 (4) |
C11D | 0.630 (3) | 0.5094 (17) | 0.5707 (7) | 0.067 (9)* | 0.394 (4) |
C12D | 0.516 (3) | 0.472 (2) | 0.6034 (9) | 0.069 (9)* | 0.394 (4) |
H12D | 0.3817 | 0.4986 | 0.6086 | 0.083* | 0.394 (4) |
C13D | 0.593 (3) | 0.3985 (19) | 0.6286 (7) | 0.079 (9)* | 0.394 (4) |
H13D | 0.5145 | 0.3772 | 0.6517 | 0.095* | 0.394 (4) |
C14D | 0.5514 (16) | 0.5918 (6) | 0.5446 (3) | 0.078 (2) | 0.394 (4) |
C15D | 1.037 (4) | 0.4274 (18) | 0.7071 (9) | 0.089 (9)* | 0.394 (4) |
H15D | 1.0536 | 0.4234 | 0.6772 | 0.107* | 0.394 (4) |
C16D | 1.245 (4) | 0.421 (3) | 0.7257 (12) | 0.070 (10)* | 0.394 (4) |
H16D | 1.3299 | 0.4749 | 0.7162 | 0.105* | 0.394 (4) |
H16E | 1.2333 | 0.4235 | 0.7551 | 0.105* | 0.394 (4) |
H16F | 1.3093 | 0.3586 | 0.7178 | 0.105* | 0.394 (4) |
C17D | 0.929 (6) | 0.5280 (18) | 0.7170 (11) | 0.076 (10)* | 0.394 (4) |
H17D | 0.7932 | 0.5296 | 0.7044 | 0.114* | 0.394 (4) |
H17E | 0.9142 | 0.5349 | 0.7463 | 0.114* | 0.394 (4) |
H17F | 1.0121 | 0.5817 | 0.7065 | 0.114* | 0.394 (4) |
C18D | 0.627 (5) | 0.237 (3) | 0.8195 (7) | 0.117 (10)* | 0.394 (4) |
H18D | 0.6491 | 0.1650 | 0.8173 | 0.141* | 0.394 (4) |
C19D | 0.777 (6) | 0.252 (3) | 0.8538 (8) | 0.101 (11)* | 0.394 (4) |
H19D | 0.9166 | 0.2552 | 0.8430 | 0.152* | 0.394 (4) |
H19E | 0.7455 | 0.3139 | 0.8676 | 0.152* | 0.394 (4) |
H19F | 0.7661 | 0.1982 | 0.8729 | 0.152* | 0.394 (4) |
C20D | 0.399 (5) | 0.230 (3) | 0.8291 (12) | 0.119 (15)* | 0.394 (4) |
H20D | 0.3219 | 0.2206 | 0.8041 | 0.178* | 0.394 (4) |
H20E | 0.3748 | 0.1755 | 0.8474 | 0.178* | 0.394 (4) |
H20F | 0.3542 | 0.2911 | 0.8420 | 0.178* | 0.394 (4) |
C21D | 0.603 (5) | 0.149 (2) | 0.6653 (8) | 0.091 (10)* | 0.394 (4) |
H21D | 0.4761 | 0.1791 | 0.6536 | 0.109* | 0.394 (4) |
C22D | 0.784 (3) | 0.1734 (14) | 0.6354 (6) | 0.082 (7)* | 0.394 (4) |
H22D | 0.8910 | 0.1223 | 0.6373 | 0.098* | 0.394 (4) |
H22E | 0.7328 | 0.1749 | 0.6073 | 0.098* | 0.394 (4) |
C23D | 0.562 (5) | 0.0415 (17) | 0.6701 (8) | 0.119 (10)* | 0.394 (4) |
H23D | 0.5293 | 0.0132 | 0.6437 | 0.178* | 0.394 (4) |
H23E | 0.6834 | 0.0095 | 0.6812 | 0.178* | 0.394 (4) |
H23F | 0.4458 | 0.0319 | 0.6884 | 0.178* | 0.394 (4) |
O1P | 1.122 (6) | 0.304 (3) | 0.6524 (14) | 0.082 (9) | 0.233 (4) |
O2P | 0.6682 (10) | 0.6314 (4) | 0.51864 (18) | 0.094 (2) | 0.233 (4) |
O3P | 0.3655 (11) | 0.6146 (5) | 0.54890 (18) | 0.102 (2) | 0.233 (4) |
C6P | 0.676 (5) | 0.214 (2) | 0.7053 (8) | 0.072 (12)* | 0.233 (4) |
C1P | 0.807 (5) | 0.295 (2) | 0.7009 (6) | 0.065 (10)* | 0.233 (4) |
C2P | 0.873 (5) | 0.347 (2) | 0.7353 (8) | 0.059 (9)* | 0.233 (4) |
C3P | 0.807 (5) | 0.318 (2) | 0.7741 (7) | 0.083 (11)* | 0.233 (4) |
H3P | 0.8527 | 0.3538 | 0.7976 | 0.100* | 0.233 (4) |
C4P | 0.677 (5) | 0.237 (2) | 0.7786 (7) | 0.071 (11)* | 0.233 (4) |
C5P | 0.610 (5) | 0.184 (2) | 0.7442 (9) | 0.081 (12)* | 0.233 (4) |
H5P | 0.5203 | 0.1290 | 0.7472 | 0.097* | 0.233 (4) |
C7P | 0.946 (4) | 0.3482 (16) | 0.6705 (6) | 0.057 (8)* | 0.233 (4) |
C8P | 0.836 (4) | 0.4077 (13) | 0.6366 (5) | 0.050 (8)* | 0.233 (4) |
C9P | 0.958 (3) | 0.4502 (17) | 0.6060 (7) | 0.082 (10)* | 0.233 (4) |
H9P | 1.1029 | 0.4380 | 0.6054 | 0.098* | 0.233 (4) |
C10P | 0.867 (4) | 0.5103 (17) | 0.5764 (6) | 0.072 (10)* | 0.233 (4) |
H10P | 0.9501 | 0.5393 | 0.5555 | 0.086* | 0.233 (4) |
C11P | 0.654 (4) | 0.5281 (14) | 0.5773 (6) | 0.075 (11)* | 0.233 (4) |
C12P | 0.533 (3) | 0.486 (2) | 0.6078 (8) | 0.067 (12)* | 0.233 (4) |
H12P | 0.3878 | 0.4978 | 0.6085 | 0.081* | 0.233 (4) |
C13P | 0.624 (4) | 0.426 (2) | 0.6375 (7) | 0.060 (10)* | 0.233 (4) |
H13P | 0.5406 | 0.3965 | 0.6583 | 0.072* | 0.233 (4) |
C14P | 0.5514 (16) | 0.5918 (6) | 0.5446 (3) | 0.078 (2) | 0.233 (4) |
C15P | 0.995 (5) | 0.421 (2) | 0.7106 (9) | 0.065 (11)* | 0.233 (4) |
C16P | 1.228 (6) | 0.432 (4) | 0.7166 (17) | 0.089 (19)* | 0.233 (4) |
H16G | 1.2802 | 0.4824 | 0.6984 | 0.134* | 0.233 (4) |
H16H | 1.2556 | 0.4508 | 0.7446 | 0.134* | 0.233 (4) |
H16I | 1.2952 | 0.3697 | 0.7108 | 0.134* | 0.233 (4) |
C17P | 0.910 (10) | 0.526 (2) | 0.7056 (17) | 0.11 (2)* | 0.233 (4) |
H17G | 1.0052 | 0.5645 | 0.6891 | 0.167* | 0.233 (4) |
H17H | 0.7763 | 0.5238 | 0.6924 | 0.167* | 0.233 (4) |
H17I | 0.8966 | 0.5567 | 0.7322 | 0.167* | 0.233 (4) |
C18P | 0.604 (6) | 0.202 (3) | 0.8207 (9) | 0.084 (11)* | 0.233 (4) |
H18P | 0.5336 | 0.1368 | 0.8205 | 0.101* | 0.233 (4) |
C19P | 0.788 (8) | 0.208 (4) | 0.8500 (13) | 0.113 (17)* | 0.233 (4) |
H19G | 0.7453 | 0.1858 | 0.8769 | 0.170* | 0.233 (4) |
H19H | 0.8985 | 0.1656 | 0.8402 | 0.170* | 0.233 (4) |
H19I | 0.8364 | 0.2752 | 0.8515 | 0.170* | 0.233 (4) |
C20P | 0.456 (8) | 0.291 (4) | 0.8305 (16) | 0.14 (2)* | 0.233 (4) |
H20G | 0.3378 | 0.2887 | 0.8123 | 0.217* | 0.233 (4) |
H20H | 0.4092 | 0.2860 | 0.8584 | 0.217* | 0.233 (4) |
H20I | 0.5303 | 0.3521 | 0.8266 | 0.217* | 0.233 (4) |
C21P | 0.593 (6) | 0.152 (3) | 0.6700 (12) | 0.084 (12)* | 0.233 (4) |
H21P | 0.5575 | 0.1968 | 0.6473 | 0.100* | 0.233 (4) |
C22P | 0.768 (8) | 0.082 (4) | 0.6554 (16) | 0.114 (16)* | 0.233 (4) |
H22F | 0.7187 | 0.0421 | 0.6330 | 0.171* | 0.233 (4) |
H22G | 0.8856 | 0.1210 | 0.6465 | 0.171* | 0.233 (4) |
H22H | 0.8100 | 0.0395 | 0.6777 | 0.171* | 0.233 (4) |
C23P | 0.401 (7) | 0.088 (4) | 0.680 (2) | 0.116 (19)* | 0.233 (4) |
H23G | 0.3608 | 0.0518 | 0.6555 | 0.173* | 0.233 (4) |
H23H | 0.4342 | 0.0421 | 0.7013 | 0.173* | 0.233 (4) |
H23I | 0.2884 | 0.1304 | 0.6882 | 0.173* | 0.233 (4) |
O1Z | 1.107 (6) | 0.283 (5) | 0.6572 (17) | 0.083 (10)* | 0.164 (4) |
O2Z | 0.6682 (10) | 0.6314 (4) | 0.51864 (18) | 0.094 (2) | 0.164 (4) |
O3Z | 0.3655 (11) | 0.6146 (5) | 0.54890 (18) | 0.102 (2) | 0.164 (4) |
C6Z | 0.754 (6) | 0.217 (2) | 0.7086 (8) | 0.055 (10)* | 0.164 (4) |
C1Z | 0.861 (6) | 0.305 (2) | 0.7019 (7) | 0.061 (11)* | 0.164 (4) |
C2Z | 0.888 (6) | 0.372 (2) | 0.7339 (9) | 0.078 (12)* | 0.164 (4) |
C3Z | 0.809 (6) | 0.351 (2) | 0.7726 (8) | 0.084 (13)* | 0.164 (4) |
H3Z | 0.8283 | 0.3969 | 0.7944 | 0.101* | 0.164 (4) |
C4Z | 0.703 (6) | 0.263 (3) | 0.7793 (8) | 0.080 (13)* | 0.164 (4) |
C5Z | 0.676 (5) | 0.196 (2) | 0.7474 (9) | 0.077 (12)* | 0.164 (4) |
H5Z | 0.6029 | 0.1351 | 0.7520 | 0.093* | 0.164 (4) |
C7Z | 0.885 (6) | 0.287 (2) | 0.6561 (9) | 0.082 (13)* | 0.164 (4) |
C8Z | 0.799 (6) | 0.366 (2) | 0.6264 (10) | 0.064 (13)* | 0.164 (4) |
C9Z | 0.883 (7) | 0.376 (3) | 0.5873 (11) | 0.071 (13)* | 0.164 (4) |
H9Z | 0.9930 | 0.3345 | 0.5787 | 0.085* | 0.164 (4) |
C10Z | 0.805 (6) | 0.448 (3) | 0.5608 (9) | 0.057 (12)* | 0.164 (4) |
H10Z | 0.8622 | 0.4556 | 0.5341 | 0.069* | 0.164 (4) |
C11Z | 0.643 (4) | 0.5094 (14) | 0.5735 (8) | 0.070 (14)* | 0.164 (4) |
C12Z | 0.559 (5) | 0.499 (2) | 0.6124 (10) | 0.066 (12)* | 0.164 (4) |
H12Z | 0.4491 | 0.5410 | 0.6211 | 0.079* | 0.164 (4) |
C13Z | 0.637 (6) | 0.427 (3) | 0.6390 (9) | 0.065 (13)* | 0.164 (4) |
H13Z | 0.5799 | 0.4198 | 0.6657 | 0.078* | 0.164 (4) |
C14Z | 0.5514 (16) | 0.5918 (6) | 0.5446 (3) | 0.078 (2) | 0.164 (4) |
C15Z | 1.006 (7) | 0.464 (3) | 0.7228 (15) | 0.078 (13)* | 0.164 (4) |
H15Z | 1.0228 | 0.4620 | 0.6928 | 0.094* | 0.164 (4) |
C16Z | 1.218 (6) | 0.448 (4) | 0.7399 (19) | 0.10 (2)* | 0.164 (4) |
H16J | 1.2701 | 0.3845 | 0.7309 | 0.143* | 0.164 (4) |
H16K | 1.3101 | 0.4997 | 0.7304 | 0.143* | 0.164 (4) |
H16L | 1.2121 | 0.4493 | 0.7694 | 0.143* | 0.164 (4) |
C17Z | 0.888 (8) | 0.555 (3) | 0.7312 (18) | 0.074 (16)* | 0.164 (4) |
H17J | 0.7549 | 0.5514 | 0.7175 | 0.110* | 0.164 (4) |
H17K | 0.8659 | 0.5612 | 0.7603 | 0.110* | 0.164 (4) |
H17L | 0.9638 | 0.6116 | 0.7213 | 0.110* | 0.164 (4) |
C18Z | 0.616 (9) | 0.238 (4) | 0.8211 (11) | 0.110 (14)* | 0.164 (4) |
H18Z | 0.6510 | 0.1690 | 0.8288 | 0.132* | 0.164 (4) |
C19Z | 0.748 (10) | 0.311 (5) | 0.8454 (15) | 0.12 (2)* | 0.164 (4) |
H19J | 0.7135 | 0.3068 | 0.8741 | 0.174* | 0.164 (4) |
H19K | 0.8931 | 0.2964 | 0.8416 | 0.174* | 0.164 (4) |
H19L | 0.7201 | 0.3778 | 0.8358 | 0.174* | 0.164 (4) |
C20Z | 0.385 (8) | 0.259 (7) | 0.830 (2) | 0.07 (2)* | 0.164 (4) |
H20J | 0.3531 | 0.2392 | 0.8579 | 0.107* | 0.164 (4) |
H20K | 0.3588 | 0.3292 | 0.8272 | 0.107* | 0.164 (4) |
H20L | 0.2988 | 0.2226 | 0.8114 | 0.107* | 0.164 (4) |
C21Z | 0.764 (6) | 0.181 (2) | 0.6646 (9) | 0.092 (13)* | 0.164 (4) |
C22Z | 0.913 (8) | 0.093 (3) | 0.6626 (16) | 0.101 (18)* | 0.164 (4) |
H22I | 0.9209 | 0.0691 | 0.6348 | 0.152* | 0.164 (4) |
H22J | 1.0487 | 0.1134 | 0.6717 | 0.152* | 0.164 (4) |
H22K | 0.8619 | 0.0407 | 0.6801 | 0.152* | 0.164 (4) |
C23Z | 0.567 (7) | 0.167 (4) | 0.6392 (17) | 0.12 (2)* | 0.164 (4) |
H23J | 0.6043 | 0.1437 | 0.6122 | 0.184* | 0.164 (4) |
H23K | 0.4787 | 0.1186 | 0.6523 | 0.184* | 0.164 (4) |
H23L | 0.4949 | 0.2292 | 0.6370 | 0.184* | 0.164 (4) |
N1 | 0.0735 (10) | 0.6664 (5) | 0.49207 (18) | 0.075 (2) | |
H1A | 0.1778 | 0.6458 | 0.5080 | 0.090* | |
H1B | −0.0479 | 0.6494 | 0.5034 | 0.090* | |
H1C | 0.0795 | 0.7324 | 0.4894 | 0.090* | |
C24 | 0.3064 (16) | 0.6478 (8) | 0.4332 (3) | 0.114 (4) | |
H24A | 0.4130 | 0.6303 | 0.4527 | 0.171* | |
H24B | 0.3101 | 0.7183 | 0.4283 | 0.171* | |
H24C | 0.3303 | 0.6129 | 0.4079 | 0.171* | |
C25 | 0.0920 (15) | 0.6188 (8) | 0.4505 (3) | 0.084 (3) | |
H25 | −0.0157 | 0.6473 | 0.4326 | 0.101* | |
C26 | 0.055 (2) | 0.5087 (9) | 0.4535 (3) | 0.094 (3) | |
C27 | −0.132 (2) | 0.4714 (12) | 0.4399 (4) | 0.123 (4) | |
H27 | −0.2352 | 0.5147 | 0.4305 | 0.148* | |
C28 | −0.169 (3) | 0.3688 (17) | 0.4400 (5) | 0.174 (7) | |
H28 | −0.2924 | 0.3427 | 0.4296 | 0.208* | |
C29 | −0.022 (5) | 0.309 (2) | 0.4555 (8) | 0.221 (14) | |
H29 | −0.0488 | 0.2413 | 0.4564 | 0.265* | |
C30 | 0.163 (4) | 0.3410 (16) | 0.4699 (6) | 0.190 (8) | |
H30 | 0.2624 | 0.2967 | 0.4798 | 0.228* | |
C31 | 0.200 (3) | 0.4460 (12) | 0.4694 (4) | 0.148 (5) | |
H31 | 0.3236 | 0.4713 | 0.4800 | 0.177* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.079 (15) | 0.086 (17) | 0.085 (14) | 0.016 (15) | 0.020 (14) | 0.014 (14) |
O2 | 0.084 (4) | 0.116 (5) | 0.083 (4) | 0.005 (4) | 0.019 (4) | 0.038 (4) |
O3 | 0.078 (4) | 0.153 (5) | 0.074 (4) | 0.027 (5) | −0.002 (4) | 0.035 (4) |
C14 | 0.089 (6) | 0.090 (6) | 0.055 (5) | 0.003 (6) | −0.013 (6) | 0.008 (4) |
O1D | 0.071 (11) | 0.089 (16) | 0.082 (12) | 0.015 (13) | 0.017 (11) | 0.008 (12) |
O2D | 0.084 (4) | 0.116 (5) | 0.083 (4) | 0.005 (4) | 0.019 (4) | 0.038 (4) |
O3D | 0.078 (4) | 0.153 (5) | 0.074 (4) | 0.027 (5) | −0.002 (4) | 0.035 (4) |
C14D | 0.089 (6) | 0.090 (6) | 0.055 (5) | 0.003 (6) | −0.013 (6) | 0.008 (4) |
O1P | 0.075 (13) | 0.088 (17) | 0.083 (16) | 0.008 (14) | 0.019 (13) | 0.023 (14) |
O2P | 0.084 (4) | 0.116 (5) | 0.083 (4) | 0.005 (4) | 0.019 (4) | 0.038 (4) |
O3P | 0.078 (4) | 0.153 (5) | 0.074 (4) | 0.027 (5) | −0.002 (4) | 0.035 (4) |
C14P | 0.089 (6) | 0.090 (6) | 0.055 (5) | 0.003 (6) | −0.013 (6) | 0.008 (4) |
O2Z | 0.084 (4) | 0.116 (5) | 0.083 (4) | 0.005 (4) | 0.019 (4) | 0.038 (4) |
O3Z | 0.078 (4) | 0.153 (5) | 0.074 (4) | 0.027 (5) | −0.002 (4) | 0.035 (4) |
C14Z | 0.089 (6) | 0.090 (6) | 0.055 (5) | 0.003 (6) | −0.013 (6) | 0.008 (4) |
N1 | 0.058 (4) | 0.098 (5) | 0.069 (5) | 0.005 (4) | 0.003 (4) | 0.011 (4) |
C24 | 0.114 (9) | 0.151 (9) | 0.076 (6) | 0.004 (8) | 0.033 (6) | 0.006 (6) |
C25 | 0.082 (7) | 0.115 (8) | 0.056 (6) | 0.018 (6) | 0.000 (5) | 0.006 (5) |
C26 | 0.119 (11) | 0.104 (9) | 0.058 (6) | 0.009 (9) | −0.005 (7) | −0.004 (6) |
C27 | 0.106 (11) | 0.153 (13) | 0.111 (9) | −0.013 (10) | 0.022 (9) | −0.018 (8) |
C28 | 0.18 (2) | 0.18 (2) | 0.153 (15) | −0.078 (16) | 0.030 (14) | −0.042 (14) |
C29 | 0.32 (5) | 0.16 (2) | 0.19 (2) | −0.04 (2) | 0.03 (3) | 0.012 (15) |
C30 | 0.26 (3) | 0.134 (18) | 0.175 (17) | 0.048 (17) | 0.012 (17) | 0.023 (12) |
C31 | 0.195 (16) | 0.118 (11) | 0.130 (11) | −0.001 (12) | −0.042 (11) | 0.008 (8) |
O1—C7 | 1.22 (2) | C3P—H3P | 0.9480 |
O2—C14 | 1.247 (9) | C4P—C5P | 1.3866 |
O3—C14 | 1.237 (10) | C4P—C18P | 1.52 (2) |
C6—C5 | 1.3806 | C5P—H5P | 0.9466 |
C6—C1 | 1.3900 | C7P—C8P | 1.535 (18) |
C6—C21 | 1.51 (2) | C7P—C15P | 1.66 (2) |
C1—C2 | 1.3932 | C8P—C13P | 1.3809 |
C1—C7 | 1.51 (2) | C8P—C9P | 1.3857 |
C2—C3 | 1.3925 | C9P—C10P | 1.3840 |
C2—C15 | 1.54 (2) | C9P—H9P | 0.9434 |
C3—C4 | 1.3727 | C10P—C11P | 1.3816 |
C3—H3 | 0.9279 | C10P—H10P | 0.9467 |
C4—C5 | 1.3817 | C11P—C12P | 1.3826 |
C4—C18 | 1.54 (2) | C11P—C14P | 1.514 (14) |
C5—H5 | 0.9267 | C12P—C13P | 1.3864 |
C7—C8 | 1.49 (2) | C12P—H12P | 0.9436 |
C8—C13 | 1.3688 | C13P—H13P | 0.9466 |
C8—C9 | 1.3767 | C15P—C16P | 1.51 (2) |
C9—C10 | 1.3691 | C15P—C17P | 1.52 (2) |
C9—H9 | 0.9241 | C16P—H16G | 0.9600 |
C10—C11 | 1.3733 | C16P—H16H | 0.9600 |
C10—H10 | 0.9265 | C16P—H16I | 0.9600 |
C11—C12 | 1.3682 | C17P—H17G | 0.9600 |
C11—C14 | 1.535 (17) | C17P—H17H | 0.9600 |
C12—C13 | 1.3789 | C17P—H17I | 0.9600 |
C12—H12 | 0.9239 | C18P—C19P | 1.52 (3) |
C13—H13 | 0.9265 | C18P—C20P | 1.55 (3) |
C15—C17 | 1.52 (3) | C18P—H18P | 0.9800 |
C15—C16 | 1.53 (3) | C19P—H19G | 0.9600 |
C15—H15 | 0.9800 | C19P—H19H | 0.9600 |
C16—H16A | 0.9600 | C19P—H19I | 0.9600 |
C16—H16B | 0.9600 | C20P—H20G | 0.9600 |
C16—H16C | 0.9600 | C20P—H20H | 0.9600 |
C17—H17A | 0.9600 | C20P—H20I | 0.9600 |
C17—H17B | 0.9600 | C21P—C23P | 1.53 (3) |
C17—H17C | 0.9600 | C21P—C22P | 1.54 (3) |
C18—C19 | 1.50 (3) | C21P—H21P | 0.9800 |
C18—C20 | 1.51 (3) | C22P—H22F | 0.9600 |
C18—H18 | 0.9800 | C22P—H22G | 0.9600 |
C19—H19A | 0.9600 | C22P—H22H | 0.9600 |
C19—H19B | 0.9600 | C23P—H23G | 0.9600 |
C19—H19C | 0.9600 | C23P—H23H | 0.9600 |
C20—H20A | 0.9600 | C23P—H23I | 0.9600 |
C20—H20B | 0.9600 | O1Z—C7Z | 1.42 (2) |
C20—H20C | 0.9600 | O2Z—C14Z | 1.247 (9) |
C21—C22 | 1.53 (3) | O3Z—C14Z | 1.237 (10) |
C21—C23 | 1.57 (2) | C6Z—C5Z | 1.3853 |
C21—H21 | 0.9800 | C6Z—C1Z | 1.3878 |
C22—H22A | 0.9600 | C6Z—C21Z | 1.51 (2) |
C22—H22B | 0.9600 | C1Z—C2Z | 1.3860 |
C22—H22C | 0.9600 | C1Z—C7Z | 1.52 (2) |
C23—H23A | 0.9600 | C2Z—C3Z | 1.3852 |
C23—H23B | 0.9600 | C2Z—C15Z | 1.49 (2) |
C23—H23C | 0.9600 | C3Z—C4Z | 1.3843 |
O1D—C7D | 1.45 (2) | C3Z—H3Z | 0.9483 |
O2D—C14D | 1.247 (9) | C4Z—C5Z | 1.3870 |
O3D—C14D | 1.237 (10) | C4Z—C18Z | 1.51 (2) |
C6D—C5D | 1.3795 | C5Z—H5Z | 0.9478 |
C6D—C1D | 1.3916 | C7Z—C8Z | 1.54 (2) |
C6D—C21D | 1.521 (19) | C7Z—C21Z | 1.64 (2) |
C1D—C2D | 1.3719 | C8Z—C13Z | 1.3840 |
C1D—C7D | 1.552 (17) | C8Z—C9Z | 1.3877 |
C2D—C3D | 1.4015 | C9Z—C10Z | 1.3838 |
C2D—C15D | 1.506 (19) | C9Z—H9Z | 0.9440 |
C3D—C4D | 1.4202 | C10Z—C11Z | 1.3854 |
C3D—H3D | 0.9477 | C10Z—H10Z | 0.9472 |
C4D—C5D | 1.3935 | C11Z—C12Z | 1.3826 |
C4D—C18D | 1.546 (19) | C11Z—C14Z | 1.566 (17) |
C5D—H5D | 0.9459 | C12Z—C13Z | 1.3910 |
C7D—C22D | 1.478 (19) | C12Z—H12Z | 0.9436 |
C7D—C8D | 1.525 (17) | C13Z—H13Z | 0.9451 |
C8D—C13D | 1.3687 | C15Z—C17Z | 1.46 (3) |
C8D—C9D | 1.3785 | C15Z—C16Z | 1.48 (3) |
C9D—C10D | 1.3774 | C15Z—H15Z | 0.9800 |
C9D—H9D | 0.9442 | C16Z—H16J | 0.9600 |
C10D—C11D | 1.4032 | C16Z—H16K | 0.9600 |
C10D—H10D | 0.9477 | C16Z—H16L | 0.9600 |
C11D—C12D | 1.3789 | C17Z—H17J | 0.9600 |
C11D—C14D | 1.481 (13) | C17Z—H17K | 0.9600 |
C12D—C13D | 1.3795 | C17Z—H17L | 0.9600 |
C12D—H12D | 0.9446 | C18Z—C19Z | 1.52 (3) |
C13D—H13D | 0.9472 | C18Z—C20Z | 1.53 (3) |
C15D—C16D | 1.47 (2) | C18Z—H18Z | 0.9800 |
C15D—C17D | 1.55 (2) | C19Z—H19J | 0.9600 |
C15D—H15D | 0.9800 | C19Z—H19K | 0.9600 |
C16D—H16D | 0.9600 | C19Z—H19L | 0.9600 |
C16D—H16E | 0.9600 | C20Z—H20J | 0.9600 |
C16D—H16F | 0.9600 | C20Z—H20K | 0.9600 |
C17D—H17D | 0.9600 | C20Z—H20L | 0.9600 |
C17D—H17E | 0.9600 | C21Z—C22Z | 1.51 (2) |
C17D—H17F | 0.9600 | C21Z—C23Z | 1.52 (2) |
C18D—C19D | 1.49 (2) | C22Z—H22I | 0.9600 |
C18D—C20D | 1.49 (2) | C22Z—H22J | 0.9600 |
C18D—H18D | 0.9800 | C22Z—H22K | 0.9600 |
C19D—H19D | 0.9600 | C23Z—H23J | 0.9600 |
C19D—H19E | 0.9600 | C23Z—H23K | 0.9600 |
C19D—H19F | 0.9600 | C23Z—H23L | 0.9600 |
C20D—H20D | 0.9600 | N1—C25 | 1.500 (10) |
C20D—H20E | 0.9600 | N1—H1A | 0.8900 |
C20D—H20F | 0.9600 | N1—H1B | 0.8900 |
C21D—C23D | 1.48 (2) | N1—H1C | 0.8900 |
C21D—C22D | 1.55 (2) | C24—C25 | 1.533 (12) |
C21D—H21D | 0.9800 | C24—H24A | 0.9600 |
C22D—H22D | 0.9700 | C24—H24B | 0.9600 |
C22D—H22E | 0.9700 | C24—H24C | 0.9600 |
C23D—H23D | 0.9600 | C25—C26 | 1.500 (13) |
C23D—H23E | 0.9600 | C25—H25 | 0.9800 |
C23D—H23F | 0.9600 | C26—C31 | 1.353 (16) |
O1P—C7P | 1.40 (2) | C26—C27 | 1.373 (16) |
O2P—C14P | 1.247 (9) | C27—C28 | 1.397 (19) |
O3P—C14P | 1.237 (10) | C27—H27 | 0.9300 |
C6P—C1P | 1.3840 | C28—C29 | 1.33 (3) |
C6P—C5P | 1.3871 | C28—H28 | 0.9300 |
C6P—C21P | 1.51 (2) | C29—C30 | 1.34 (3) |
C1P—C2P | 1.3870 | C29—H29 | 0.9300 |
C1P—C7P | 1.511 (19) | C30—C31 | 1.43 (2) |
C2P—C3P | 1.3870 | C30—H30 | 0.9300 |
C2P—C15P | 1.50 (2) | C31—H31 | 0.9300 |
C3P—C4P | 1.3809 | ||
C5—C6—C1 | 118.2 | C1P—C7P—C8P | 116.5 (19) |
C5—C6—C21 | 119.8 (19) | O1P—C7P—C15P | 116 (3) |
C1—C6—C21 | 122.0 (19) | C1P—C7P—C15P | 83.0 (14) |
C6—C1—C2 | 121.0 | C8P—C7P—C15P | 110.1 (16) |
C6—C1—C7 | 115.7 (17) | C13P—C8P—C9P | 119.8 |
C2—C1—C7 | 123.3 (17) | C13P—C8P—C7P | 121.8 (15) |
C3—C2—C1 | 118.24 (7) | C9P—C8P—C7P | 118.2 (15) |
C3—C2—C15 | 121 (2) | C10P—C9P—C8P | 120.2 |
C1—C2—C15 | 120 (2) | C10P—C9P—H9P | 120.0 |
C4—C3—C2 | 122.2 | C8P—C9P—H9P | 119.8 |
C4—C3—H3 | 118.9 | C11P—C10P—C9P | 120.0 |
C2—C3—H3 | 118.9 | C11P—C10P—H10P | 119.8 |
C3—C4—C5 | 117.8 | C9P—C10P—H10P | 120.1 |
C3—C4—C18 | 120 (2) | C10P—C11P—C12P | 119.8 |
C5—C4—C18 | 122 (2) | C10P—C11P—C14P | 120.8 (16) |
C6—C5—C4 | 122.64 (6) | C12P—C11P—C14P | 119.4 (16) |
C6—C5—H5 | 118.6 | C11P—C12P—C13P | 120.2 |
C4—C5—H5 | 118.7 | C11P—C12P—H12P | 120.0 |
O1—C7—C8 | 120 (3) | C13P—C12P—H12P | 119.8 |
O1—C7—C1 | 121 (3) | C8P—C13P—C12P | 119.9 |
C8—C7—C1 | 119 (2) | C8P—C13P—H13P | 119.8 |
C13—C8—C9 | 118.4 | C12P—C13P—H13P | 120.2 |
C13—C8—C7 | 122.3 (19) | O3P—C14P—O2P | 123.2 (7) |
C9—C8—C7 | 119.3 (19) | O3P—C14P—C11P | 118.7 (13) |
C10—C9—C8 | 120.7 | O2P—C14P—C11P | 117.1 (13) |
C10—C9—H9 | 119.7 | C2P—C15P—C16P | 121 (3) |
C8—C9—H9 | 119.6 | C2P—C15P—C17P | 119 (3) |
C9—C10—C11 | 120.9 | C16P—C15P—C17P | 106 (3) |
C9—C10—H10 | 119.7 | C2P—C15P—C7P | 86.2 (15) |
C11—C10—H10 | 119.4 | C16P—C15P—C7P | 110 (2) |
C12—C11—C10 | 118.5 | C17P—C15P—C7P | 113 (3) |
C12—C11—C14 | 118 (2) | C15P—C16P—H16G | 109.5 |
C10—C11—C14 | 123.4 (19) | C15P—C16P—H16H | 109.5 |
C11—C12—C13 | 120.7 | H16G—C16P—H16H | 109.5 |
C11—C12—H12 | 119.6 | C15P—C16P—H16I | 109.5 |
C13—C12—H12 | 119.7 | H16G—C16P—H16I | 109.5 |
C8—C13—C12 | 120.8 | H16H—C16P—H16I | 109.5 |
C8—C13—H13 | 119.4 | C15P—C17P—H17G | 109.5 |
C12—C13—H13 | 119.8 | C15P—C17P—H17H | 109.5 |
O3—C14—O2 | 123.2 (7) | H17G—C17P—H17H | 109.5 |
O3—C14—C11 | 120.8 (15) | C15P—C17P—H17I | 109.5 |
O2—C14—C11 | 116.0 (15) | H17G—C17P—H17I | 109.5 |
C17—C15—C16 | 112 (3) | H17H—C17P—H17I | 109.5 |
C17—C15—C2 | 112 (3) | C19P—C18P—C4P | 108 (3) |
C16—C15—C2 | 110 (3) | C19P—C18P—C20P | 108 (3) |
C17—C15—H15 | 107.9 | C4P—C18P—C20P | 98 (2) |
C16—C15—H15 | 107.9 | C19P—C18P—H18P | 114.0 |
C2—C15—H15 | 107.9 | C4P—C18P—H18P | 114.0 |
C15—C16—H16A | 109.5 | C20P—C18P—H18P | 114.0 |
C15—C16—H16B | 109.5 | C18P—C19P—H19G | 109.5 |
H16A—C16—H16B | 109.5 | C18P—C19P—H19H | 109.5 |
C15—C16—H16C | 109.5 | H19G—C19P—H19H | 109.5 |
H16A—C16—H16C | 109.5 | C18P—C19P—H19I | 109.5 |
H16B—C16—H16C | 109.5 | H19G—C19P—H19I | 109.5 |
C15—C17—H17A | 109.5 | H19H—C19P—H19I | 109.5 |
C15—C17—H17B | 109.5 | C18P—C20P—H20G | 109.5 |
H17A—C17—H17B | 109.5 | C18P—C20P—H20H | 109.5 |
C15—C17—H17C | 109.5 | H20G—C20P—H20H | 109.5 |
H17A—C17—H17C | 109.5 | C18P—C20P—H20I | 109.5 |
H17B—C17—H17C | 109.5 | H20G—C20P—H20I | 109.5 |
C19—C18—C20 | 113 (3) | H20H—C20P—H20I | 109.5 |
C19—C18—C4 | 115 (3) | C6P—C21P—C23P | 116 (3) |
C20—C18—C4 | 108 (3) | C6P—C21P—C22P | 108 (3) |
C19—C18—H18 | 106.6 | C23P—C21P—C22P | 108 (3) |
C20—C18—H18 | 106.6 | C6P—C21P—H21P | 108.2 |
C4—C18—H18 | 106.6 | C23P—C21P—H21P | 108.2 |
C18—C19—H19A | 109.5 | C22P—C21P—H21P | 108.2 |
C18—C19—H19B | 109.5 | C21P—C22P—H22F | 109.5 |
H19A—C19—H19B | 109.5 | C21P—C22P—H22G | 109.5 |
C18—C19—H19C | 109.5 | H22F—C22P—H22G | 109.5 |
H19A—C19—H19C | 109.5 | C21P—C22P—H22H | 109.5 |
H19B—C19—H19C | 109.5 | H22F—C22P—H22H | 109.5 |
C18—C20—H20A | 109.5 | H22G—C22P—H22H | 109.5 |
C18—C20—H20B | 109.5 | C21P—C23P—H23G | 109.5 |
H20A—C20—H20B | 109.5 | C21P—C23P—H23H | 109.5 |
C18—C20—H20C | 109.5 | H23G—C23P—H23H | 109.5 |
H20A—C20—H20C | 109.5 | C21P—C23P—H23I | 109.5 |
H20B—C20—H20C | 109.5 | H23G—C23P—H23I | 109.5 |
C6—C21—C22 | 108 (3) | H23H—C23P—H23I | 109.5 |
C6—C21—C23 | 109 (3) | C5Z—C6Z—C1Z | 119.9 |
C22—C21—C23 | 104 (3) | C5Z—C6Z—C21Z | 144.1 (16) |
C6—C21—H21 | 111.5 | C1Z—C6Z—C21Z | 95.8 (16) |
C22—C21—H21 | 111.5 | C2Z—C1Z—C6Z | 119.8 |
C23—C21—H21 | 111.5 | C2Z—C1Z—C7Z | 146.1 (16) |
C21—C22—H22A | 109.5 | C6Z—C1Z—C7Z | 93.8 (16) |
C21—C22—H22B | 109.5 | C3Z—C2Z—C1Z | 120.23 (6) |
H22A—C22—H22B | 109.5 | C3Z—C2Z—C15Z | 125 (2) |
C21—C22—H22C | 109.5 | C1Z—C2Z—C15Z | 115 (2) |
H22A—C22—H22C | 109.5 | C4Z—C3Z—C2Z | 119.9 |
H22B—C22—H22C | 109.5 | C4Z—C3Z—H3Z | 120.0 |
C21—C23—H23A | 109.5 | C2Z—C3Z—H3Z | 120.1 |
C21—C23—H23B | 109.5 | C3Z—C4Z—C5Z | 120.0 |
H23A—C23—H23B | 109.5 | C3Z—C4Z—C18Z | 121 (2) |
C21—C23—H23C | 109.5 | C5Z—C4Z—C18Z | 119 (2) |
H23A—C23—H23C | 109.5 | C6Z—C5Z—C4Z | 120.09 (6) |
H23B—C23—H23C | 109.5 | C6Z—C5Z—H5Z | 119.9 |
C5D—C6D—C1D | 119.3 | C4Z—C5Z—H5Z | 120.0 |
C5D—C6D—C21D | 133.2 (12) | O1Z—C7Z—C1Z | 95 (3) |
C1D—C6D—C21D | 107.3 (12) | O1Z—C7Z—C8Z | 114 (3) |
C2D—C1D—C6D | 121.7 | C1Z—C7Z—C8Z | 118 (2) |
C2D—C1D—C7D | 124.7 (12) | O1Z—C7Z—C21Z | 116 (3) |
C6D—C1D—C7D | 113.5 (11) | C1Z—C7Z—C21Z | 85.9 (16) |
C1D—C2D—C3D | 118.1 | C8Z—C7Z—C21Z | 122 (2) |
C1D—C2D—C15D | 122.1 (15) | C13Z—C8Z—C9Z | 120.0 |
C3D—C2D—C15D | 119.9 (15) | C13Z—C8Z—C7Z | 120 (2) |
C2D—C3D—C4D | 122.0 | C9Z—C8Z—C7Z | 120 (2) |
C2D—C3D—H3D | 119.1 | C10Z—C9Z—C8Z | 120.1 |
C4D—C3D—H3D | 118.9 | C10Z—C9Z—H9Z | 119.8 |
C5D—C4D—C3D | 116.7 | C8Z—C9Z—H9Z | 120.1 |
C5D—C4D—C18D | 116.1 (16) | C9Z—C10Z—C11Z | 119.8 |
C3D—C4D—C18D | 127.2 (16) | C9Z—C10Z—H10Z | 120.5 |
C6D—C5D—C4D | 122.0 | C11Z—C10Z—H10Z | 119.7 |
C6D—C5D—H5D | 119.1 | C12Z—C11Z—C10Z | 120.3 |
C4D—C5D—H5D | 119.0 | C12Z—C11Z—C14Z | 118.1 (19) |
O1D—C7D—C22D | 110.2 (18) | C10Z—C11Z—C14Z | 121.6 (19) |
O1D—C7D—C8D | 109.8 (17) | C11Z—C12Z—C13Z | 119.9 |
C22D—C7D—C8D | 112.4 (14) | C11Z—C12Z—H12Z | 120.4 |
O1D—C7D—C1D | 111.8 (18) | C13Z—C12Z—H12Z | 119.7 |
C22D—C7D—C1D | 100.8 (14) | C8Z—C13Z—C12Z | 119.9 |
C8D—C7D—C1D | 111.6 (15) | C8Z—C13Z—H13Z | 120.0 |
C13D—C8D—C9D | 118.6 | C12Z—C13Z—H13Z | 120.2 |
C13D—C8D—C7D | 123.0 (13) | O3Z—C14Z—O2Z | 123.2 (7) |
C9D—C8D—C7D | 118.4 (13) | O3Z—C14Z—C11Z | 118.0 (14) |
C10D—C9D—C8D | 121.8 | O2Z—C14Z—C11Z | 118.8 (13) |
C10D—C9D—H9D | 119.2 | C17Z—C15Z—C16Z | 122 (4) |
C8D—C9D—H9D | 119.0 | C17Z—C15Z—C2Z | 112 (2) |
C9D—C10D—C11D | 119.8 | C16Z—C15Z—C2Z | 105 (2) |
C9D—C10D—H10D | 120.3 | C17Z—C15Z—H15Z | 105.6 |
C11D—C10D—H10D | 119.9 | C16Z—C15Z—H15Z | 105.6 |
C12D—C11D—C10D | 117.5 | C2Z—C15Z—H15Z | 105.6 |
C12D—C11D—C14D | 122.1 (13) | C15Z—C16Z—H16J | 109.5 |
C10D—C11D—C14D | 120.4 (13) | C15Z—C16Z—H16K | 109.5 |
C11D—C12D—C13D | 122.0 | H16J—C16Z—H16K | 109.5 |
C11D—C12D—H12D | 119.0 | C15Z—C16Z—H16L | 109.5 |
C13D—C12D—H12D | 119.0 | H16J—C16Z—H16L | 109.5 |
C8D—C13D—C12D | 120.3 | H16K—C16Z—H16L | 109.5 |
C8D—C13D—H13D | 119.7 | C15Z—C17Z—H17J | 109.5 |
C12D—C13D—H13D | 120.0 | C15Z—C17Z—H17K | 109.5 |
O3D—C14D—O2D | 123.2 (7) | H17J—C17Z—H17K | 109.5 |
O3D—C14D—C11D | 116.5 (12) | C15Z—C17Z—H17L | 109.5 |
O2D—C14D—C11D | 120.2 (12) | H17J—C17Z—H17L | 109.5 |
C16D—C15D—C2D | 114.0 (19) | H17K—C17Z—H17L | 109.5 |
C16D—C15D—C17D | 112 (2) | C4Z—C18Z—C19Z | 97 (3) |
C2D—C15D—C17D | 107.7 (18) | C4Z—C18Z—C20Z | 119 (3) |
C16D—C15D—H15D | 107.7 | C19Z—C18Z—C20Z | 108 (3) |
C2D—C15D—H15D | 107.7 | C4Z—C18Z—H18Z | 110.6 |
C17D—C15D—H15D | 107.7 | C19Z—C18Z—H18Z | 110.6 |
C15D—C16D—H16D | 109.5 | C20Z—C18Z—H18Z | 110.6 |
C15D—C16D—H16E | 109.5 | C18Z—C19Z—H19J | 109.5 |
H16D—C16D—H16E | 109.5 | C18Z—C19Z—H19K | 109.5 |
C15D—C16D—H16F | 109.5 | H19J—C19Z—H19K | 109.5 |
H16D—C16D—H16F | 109.5 | C18Z—C19Z—H19L | 109.5 |
H16E—C16D—H16F | 109.5 | H19J—C19Z—H19L | 109.5 |
C15D—C17D—H17D | 109.5 | H19K—C19Z—H19L | 109.5 |
C15D—C17D—H17E | 109.5 | C18Z—C20Z—H20J | 109.5 |
H17D—C17D—H17E | 109.5 | C18Z—C20Z—H20K | 109.5 |
C15D—C17D—H17F | 109.5 | H20J—C20Z—H20K | 109.5 |
H17D—C17D—H17F | 109.5 | C18Z—C20Z—H20L | 109.5 |
H17E—C17D—H17F | 109.5 | H20J—C20Z—H20L | 109.5 |
C19D—C18D—C20D | 119 (2) | H20K—C20Z—H20L | 109.5 |
C19D—C18D—C4D | 121 (2) | C6Z—C21Z—C22Z | 108 (3) |
C20D—C18D—C4D | 118 (2) | C6Z—C21Z—C23Z | 121 (3) |
C19D—C18D—H18D | 95.7 | C22Z—C21Z—C23Z | 114 (3) |
C20D—C18D—H18D | 95.7 | C6Z—C21Z—C7Z | 84.4 (16) |
C4D—C18D—H18D | 95.7 | C22Z—C21Z—C7Z | 112 (3) |
C18D—C19D—H19D | 109.5 | C23Z—C21Z—C7Z | 114 (3) |
C18D—C19D—H19E | 109.5 | C21Z—C22Z—H22I | 109.5 |
H19D—C19D—H19E | 109.5 | C21Z—C22Z—H22J | 109.5 |
C18D—C19D—H19F | 109.5 | H22I—C22Z—H22J | 109.5 |
H19D—C19D—H19F | 109.5 | C21Z—C22Z—H22K | 109.5 |
H19E—C19D—H19F | 109.5 | H22I—C22Z—H22K | 109.5 |
C18D—C20D—H20D | 109.5 | H22J—C22Z—H22K | 109.5 |
C18D—C20D—H20E | 109.5 | C21Z—C23Z—H23J | 109.5 |
H20D—C20D—H20E | 109.5 | C21Z—C23Z—H23K | 109.5 |
C18D—C20D—H20F | 109.5 | H23J—C23Z—H23K | 109.5 |
H20D—C20D—H20F | 109.5 | C21Z—C23Z—H23L | 109.5 |
H20E—C20D—H20F | 109.5 | H23J—C23Z—H23L | 109.5 |
C23D—C21D—C6D | 118 (2) | H23K—C23Z—H23L | 109.5 |
C23D—C21D—C22D | 114 (2) | C25—N1—H1A | 109.5 |
C6D—C21D—C22D | 103.3 (16) | C25—N1—H1B | 109.5 |
C23D—C21D—H21D | 107.0 | H1A—N1—H1B | 109.5 |
C6D—C21D—H21D | 107.0 | C25—N1—H1C | 109.5 |
C22D—C21D—H21D | 107.0 | H1A—N1—H1C | 109.5 |
C7D—C22D—C21D | 108.9 (15) | H1B—N1—H1C | 109.5 |
C7D—C22D—H22D | 109.9 | C25—C24—H24A | 109.5 |
C21D—C22D—H22D | 109.9 | C25—C24—H24B | 109.5 |
C7D—C22D—H22E | 109.9 | H24A—C24—H24B | 109.5 |
C21D—C22D—H22E | 109.9 | C25—C24—H24C | 109.5 |
H22D—C22D—H22E | 108.3 | H24A—C24—H24C | 109.5 |
C21D—C23D—H23D | 109.5 | H24B—C24—H24C | 109.5 |
C21D—C23D—H23E | 109.5 | C26—C25—N1 | 110.4 (7) |
H23D—C23D—H23E | 109.5 | C26—C25—C24 | 114.5 (9) |
C21D—C23D—H23F | 109.5 | N1—C25—C24 | 107.0 (8) |
H23D—C23D—H23F | 109.5 | C26—C25—H25 | 108.3 |
H23E—C23D—H23F | 109.5 | N1—C25—H25 | 108.3 |
C1P—C6P—C5P | 120.0 | C24—C25—H25 | 108.3 |
C1P—C6P—C21P | 124.4 (19) | C31—C26—C27 | 119.5 (12) |
C5P—C6P—C21P | 115.6 (19) | C31—C26—C25 | 122.1 (13) |
C6P—C1P—C2P | 120.0 | C27—C26—C25 | 118.4 (13) |
C6P—C1P—C7P | 143.2 (16) | C26—C27—C28 | 120.3 (15) |
C2P—C1P—C7P | 96.1 (15) | C26—C27—H27 | 119.8 |
C3P—C2P—C1P | 119.97 (6) | C28—C27—H27 | 119.8 |
C3P—C2P—C15P | 146.5 (16) | C29—C28—C27 | 118 (2) |
C1P—C2P—C15P | 93.5 (16) | C29—C28—H28 | 120.9 |
C4P—C3P—C2P | 120.0 | C27—C28—H28 | 120.9 |
C4P—C3P—H3P | 120.1 | C28—C29—C30 | 124 (3) |
C2P—C3P—H3P | 119.8 | C28—C29—H29 | 117.8 |
C3P—C4P—C5P | 120.1 | C30—C29—H29 | 117.8 |
C3P—C4P—C18P | 121.6 (19) | C29—C30—C31 | 117 (3) |
C5P—C4P—C18P | 118.4 (19) | C29—C30—H30 | 121.5 |
C4P—C5P—C6P | 119.99 (6) | C31—C30—H30 | 121.5 |
C4P—C5P—H5P | 120.0 | C26—C31—C30 | 120.4 (16) |
C6P—C5P—H5P | 120.0 | C26—C31—H31 | 119.8 |
O1P—C7P—C1P | 123 (2) | C30—C31—H31 | 119.8 |
O1P—C7P—C8P | 107 (2) |
C31H39NO3 | Dx = 1.141 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 900 reflections |
a = 6.1975 (8) Å | θ = 5.6–18.6° |
b = 13.744 (3) Å | µ = 0.07 mm−1 |
c = 32.378 (17) Å | T = 299 K |
V = 2757.9 (16) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.10 × 0.08 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 2184 independent reflections |
Radiation source: fine-focus sealed tube | 1034 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.109 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 24.6°, θmin = 5.7° |
φ– and ω scans | h = −7→7 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −11→15 |
Tmin = 0.343, Tmax = 1.000 | l = −21→18 |
5657 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.085 | w = 1/[σ2(Fo2) + (0.0255P)2 + 1.251P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.150 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.15 e Å−3 |
2184 reflections | Δρmin = −0.12 e Å−3 |
254 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
36 restraints | Absolute structure parameter: −1.4 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.0381 (15) | 0.7615 (7) | 0.3714 (5) | 0.092 (7) | |
O2 | 0.6129 (13) | 0.3695 (6) | 0.4832 (5) | 0.080 (6) | |
O3 | 0.3123 (13) | 0.3799 (6) | 0.4464 (4) | 0.076 (6) | |
C1 | 0.814 (2) | 0.7291 (11) | 0.3138 (10) | 0.047 (9) | |
C2 | 0.679 (2) | 0.8071 (11) | 0.3023 (10) | 0.048 (10) | |
C3 | 0.633 (2) | 0.8181 (11) | 0.2618 (12) | 0.056 (10) | |
H3 | 0.5449 | 0.8702 | 0.2546 | 0.067* | |
C4 | 0.707 (2) | 0.7570 (11) | 0.2291 (9) | 0.057 (8) | |
C5 | 0.840 (2) | 0.6787 (10) | 0.2406 (9) | 0.052 (9) | |
H5 | 0.8915 | 0.6360 | 0.2206 | 0.062* | |
C6 | 0.895 (2) | 0.6651 (11) | 0.2823 (10) | 0.047 (9) | |
C7 | 0.889 (3) | 0.7137 (10) | 0.3554 (10) | 0.074 (12) | |
C8 | 0.7789 (17) | 0.6386 (8) | 0.3841 (7) | 0.043 (3)* | |
C9 | 0.5776 (18) | 0.5985 (9) | 0.3715 (6) | 0.063 (4)* | |
H9 | 0.5072 | 0.6210 | 0.3480 | 0.076* | |
C10 | 0.4899 (18) | 0.5246 (9) | 0.3956 (7) | 0.060 (4)* | |
H10 | 0.3578 | 0.4978 | 0.3881 | 0.072* | |
C11 | 0.5947 (18) | 0.4900 (9) | 0.4305 (7) | 0.050 (4)* | |
C12 | 0.7921 (18) | 0.5322 (9) | 0.4413 (7) | 0.068 (4)* | |
H12 | 0.8649 | 0.5104 | 0.4646 | 0.082* | |
C13 | 0.881 (2) | 0.6062 (9) | 0.4177 (6) | 0.057 (4)* | |
H13 | 1.0122 | 0.6334 | 0.4253 | 0.069* | |
C14 | 0.499 (3) | 0.4078 (9) | 0.4567 (8) | 0.066 (9) | |
C15 | 1.0418 (17) | 0.5779 (9) | 0.2929 (7) | 0.081 (11) | |
H15 | 1.0630 | 0.5777 | 0.3229 | 0.097* | |
C16 | 1.2596 (17) | 0.5872 (9) | 0.2732 (7) | 0.079 (10) | |
H16A | 1.3199 | 0.6497 | 0.2796 | 0.118* | |
H16B | 1.2455 | 0.5808 | 0.2438 | 0.118* | |
H16C | 1.3529 | 0.5370 | 0.2834 | 0.118* | |
C17 | 0.925 (2) | 0.4818 (9) | 0.2812 (7) | 0.106 (11) | |
H17A | 0.9272 | 0.4739 | 0.2517 | 0.160* | |
H17B | 0.7787 | 0.4841 | 0.2907 | 0.160* | |
H17C | 0.9982 | 0.4279 | 0.2939 | 0.160* | |
C18 | 0.642 (3) | 0.7791 (11) | 0.1856 (11) | 0.076 (6)* | |
H18 | 0.6464 | 0.8502 | 0.1835 | 0.091* | |
C19 | 0.4132 (19) | 0.7514 (12) | 0.1733 (9) | 0.124 (12) | |
H19A | 0.3650 | 0.7933 | 0.1514 | 0.186* | |
H19B | 0.3192 | 0.7584 | 0.1967 | 0.186* | |
H19C | 0.4111 | 0.6851 | 0.1640 | 0.186* | |
C20 | 0.795 (2) | 0.7427 (13) | 0.1526 (10) | 0.122 (15) | |
H20A | 0.7812 | 0.6735 | 0.1499 | 0.184* | |
H20B | 0.9409 | 0.7585 | 0.1602 | 0.184* | |
H20C | 0.7615 | 0.7732 | 0.1267 | 0.184* | |
C21 | 0.602 (2) | 0.8790 (10) | 0.3335 (7) | 0.068 (10) | |
H21 | 0.5847 | 0.8431 | 0.3594 | 0.082* | |
C22 | 0.776 (2) | 0.9586 (10) | 0.3416 (10) | 0.098 (12) | |
H22A | 0.7897 | 0.9991 | 0.3176 | 0.148* | |
H22B | 0.9119 | 0.9280 | 0.3474 | 0.148* | |
H22C | 0.7332 | 0.9976 | 0.3648 | 0.148* | |
C23 | 0.3839 (18) | 0.9262 (10) | 0.3243 (10) | 0.096 (10) | |
H23A | 0.2747 | 0.8768 | 0.3227 | 0.145* | |
H23B | 0.3916 | 0.9602 | 0.2984 | 0.145* | |
H23C | 0.3485 | 0.9712 | 0.3459 | 0.145* | |
N1 | 0.0364 (13) | 0.3303 (7) | 0.5092 (6) | 0.067 (8) | |
H1A | 0.0292 | 0.2659 | 0.5116 | 0.080* | |
H1B | 0.1445 | 0.3461 | 0.4924 | 0.080* | |
H1C | −0.0870 | 0.3528 | 0.4989 | 0.080* | |
C24 | 0.2877 (18) | 0.3373 (8) | 0.5666 (8) | 0.095 (10) | |
H24A | 0.4019 | 0.3637 | 0.5500 | 0.142* | |
H24B | 0.2893 | 0.2676 | 0.5648 | 0.142* | |
H24C | 0.3079 | 0.3566 | 0.5949 | 0.142* | |
C25 | 0.0751 (19) | 0.3750 (10) | 0.5514 (8) | 0.052 (4)* | |
H25 | −0.0373 | 0.3507 | 0.5700 | 0.062* | |
C26 | 0.0535 (17) | 0.4829 (9) | 0.5492 (7) | 0.057 (4)* | |
C27 | −0.138 (2) | 0.5270 (10) | 0.5596 (7) | 0.085 (5)* | |
H27 | −0.2546 | 0.4890 | 0.5679 | 0.102* | |
C28 | −0.160 (2) | 0.6307 (11) | 0.5578 (8) | 0.096 (5)* | |
H28 | −0.2863 | 0.6617 | 0.5663 | 0.115* | |
C29 | 0.010 (2) | 0.6813 (10) | 0.5433 (7) | 0.087 (5)* | |
H29 | −0.0087 | 0.7480 | 0.5400 | 0.105* | |
C30 | 0.204 (2) | 0.6443 (11) | 0.5332 (8) | 0.097 (6)* | |
H30 | 0.3195 | 0.6830 | 0.5252 | 0.116* | |
C31 | 0.2180 (19) | 0.5399 (10) | 0.5359 (7) | 0.071 (5)* | |
H31 | 0.3464 | 0.5101 | 0.5281 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.102 (7) | 0.080 (8) | 0.09 (2) | −0.046 (6) | −0.044 (9) | 0.021 (7) |
O2 | 0.053 (5) | 0.040 (7) | 0.15 (2) | 0.005 (4) | 0.006 (8) | 0.024 (7) |
O3 | 0.055 (5) | 0.087 (7) | 0.09 (2) | −0.028 (5) | −0.006 (7) | 0.021 (7) |
C1 | 0.048 (9) | 0.053 (12) | 0.04 (3) | −0.005 (8) | −0.001 (13) | −0.004 (12) |
C2 | 0.056 (9) | 0.042 (11) | 0.05 (3) | 0.003 (7) | −0.009 (14) | 0.012 (12) |
C3 | 0.059 (9) | 0.038 (10) | 0.07 (3) | 0.011 (7) | 0.002 (13) | 0.018 (13) |
C4 | 0.060 (8) | 0.054 (12) | 0.06 (3) | −0.013 (8) | −0.005 (14) | −0.006 (12) |
C5 | 0.058 (8) | 0.043 (10) | 0.05 (3) | −0.006 (7) | −0.003 (13) | −0.004 (11) |
C6 | 0.075 (10) | 0.049 (11) | 0.02 (3) | −0.016 (8) | −0.003 (14) | 0.003 (12) |
C7 | 0.056 (10) | 0.039 (11) | 0.13 (4) | 0.012 (7) | −0.030 (15) | 0.006 (12) |
C14 | 0.077 (10) | 0.026 (10) | 0.09 (3) | 0.006 (8) | 0.020 (13) | 0.006 (10) |
C15 | 0.056 (7) | 0.038 (10) | 0.15 (4) | 0.011 (7) | −0.009 (11) | 0.022 (10) |
C16 | 0.074 (8) | 0.072 (12) | 0.09 (4) | 0.010 (7) | −0.004 (12) | −0.003 (11) |
C17 | 0.094 (9) | 0.036 (10) | 0.19 (4) | 0.001 (8) | −0.012 (13) | 0.004 (10) |
C19 | 0.070 (9) | 0.153 (18) | 0.15 (4) | −0.029 (10) | −0.009 (15) | 0.010 (14) |
C20 | 0.102 (12) | 0.148 (18) | 0.12 (6) | 0.022 (12) | −0.008 (16) | −0.014 (15) |
C21 | 0.077 (9) | 0.044 (11) | 0.08 (3) | 0.003 (8) | −0.012 (12) | 0.004 (10) |
C22 | 0.095 (9) | 0.081 (13) | 0.12 (4) | −0.010 (9) | 0.016 (13) | −0.037 (13) |
C23 | 0.080 (9) | 0.081 (13) | 0.13 (4) | 0.022 (9) | −0.011 (13) | 0.012 (11) |
N1 | 0.060 (6) | 0.036 (7) | 0.11 (3) | −0.001 (5) | 0.003 (9) | 0.012 (8) |
C24 | 0.081 (8) | 0.054 (10) | 0.15 (3) | 0.011 (7) | −0.029 (13) | 0.011 (10) |
O1—C7 | 1.245 (19) | C18—H18 | 0.9800 |
O2—C14 | 1.23 (2) | C19—H19A | 0.9600 |
O3—C14 | 1.265 (17) | C19—H19B | 0.9600 |
C1—C2 | 1.41 (2) | C19—H19C | 0.9600 |
C1—C6 | 1.44 (3) | C20—H20A | 0.9600 |
C1—C7 | 1.44 (3) | C20—H20B | 0.9600 |
C2—C3 | 1.35 (4) | C20—H20C | 0.9600 |
C2—C21 | 1.49 (3) | C21—C23 | 1.529 (16) |
C3—C4 | 1.43 (4) | C21—C22 | 1.558 (16) |
C3—H3 | 0.9300 | C21—H21 | 0.9800 |
C4—C5 | 1.41 (2) | C22—H22A | 0.9600 |
C4—C18 | 1.50 (4) | C22—H22B | 0.9600 |
C5—C6 | 1.41 (3) | C22—H22C | 0.9600 |
C5—H5 | 0.9300 | C23—H23A | 0.9600 |
C6—C15 | 1.54 (2) | C23—H23B | 0.9600 |
C7—C8 | 1.55 (3) | C23—H23C | 0.9600 |
C8—C13 | 1.33 (2) | N1—C25 | 1.52 (2) |
C8—C9 | 1.424 (17) | N1—H1A | 0.8900 |
C9—C10 | 1.391 (19) | N1—H1B | 0.8900 |
C9—H9 | 0.9300 | N1—H1C | 0.8900 |
C10—C11 | 1.39 (2) | C24—C25 | 1.499 (16) |
C10—H10 | 0.9300 | C24—H24A | 0.9600 |
C11—C12 | 1.399 (15) | C24—H24B | 0.9600 |
C11—C14 | 1.53 (2) | C24—H24C | 0.9600 |
C12—C13 | 1.38 (2) | C25—C26 | 1.491 (16) |
C12—H12 | 0.9300 | C25—H25 | 0.9800 |
C13—H13 | 0.9300 | C26—C31 | 1.356 (16) |
C15—C16 | 1.499 (18) | C26—C27 | 1.376 (15) |
C15—C17 | 1.553 (16) | C27—C28 | 1.434 (16) |
C15—H15 | 0.9800 | C27—H27 | 0.9300 |
C16—H16A | 0.9600 | C28—C29 | 1.347 (19) |
C16—H16B | 0.9600 | C28—H28 | 0.9300 |
C16—H16C | 0.9600 | C29—C30 | 1.347 (17) |
C17—H17A | 0.9600 | C29—H29 | 0.9300 |
C17—H17B | 0.9600 | C30—C31 | 1.440 (16) |
C17—H17C | 0.9600 | C30—H30 | 0.9300 |
C18—C20 | 1.52 (3) | C31—H31 | 0.9300 |
C18—C19 | 1.52 (2) | ||
C2—C1—C6 | 119 (3) | C18—C19—H19A | 109.5 |
C2—C1—C7 | 123 (2) | C18—C19—H19B | 109.5 |
C6—C1—C7 | 117.5 (19) | H19A—C19—H19B | 109.5 |
C3—C2—C1 | 118 (3) | C18—C19—H19C | 109.5 |
C3—C2—C21 | 121.0 (18) | H19A—C19—H19C | 109.5 |
C1—C2—C21 | 121 (3) | H19B—C19—H19C | 109.5 |
C2—C3—C4 | 126 (2) | C18—C20—H20A | 109.5 |
C2—C3—H3 | 117.1 | C18—C20—H20B | 109.5 |
C4—C3—H3 | 117.1 | H20A—C20—H20B | 109.5 |
C5—C4—C3 | 116 (3) | C18—C20—H20C | 109.5 |
C5—C4—C18 | 124 (2) | H20A—C20—H20C | 109.5 |
C3—C4—C18 | 119.4 (19) | H20B—C20—H20C | 109.5 |
C4—C5—C6 | 120 (2) | C2—C21—C23 | 115.6 (18) |
C4—C5—H5 | 120.0 | C2—C21—C22 | 110.9 (14) |
C6—C5—H5 | 120.0 | C23—C21—C22 | 110.3 (11) |
C5—C6—C1 | 121 (2) | C2—C21—H21 | 106.5 |
C5—C6—C15 | 117 (2) | C23—C21—H21 | 106.5 |
C1—C6—C15 | 121 (3) | C22—C21—H21 | 106.5 |
O1—C7—C1 | 123 (2) | C21—C22—H22A | 109.5 |
O1—C7—C8 | 115 (3) | C21—C22—H22B | 109.5 |
C1—C7—C8 | 121.2 (16) | H22A—C22—H22B | 109.5 |
C13—C8—C9 | 121.3 (15) | C21—C22—H22C | 109.5 |
C13—C8—C7 | 120.3 (14) | H22A—C22—H22C | 109.5 |
C9—C8—C7 | 118.1 (19) | H22B—C22—H22C | 109.5 |
C10—C9—C8 | 117.6 (17) | C21—C23—H23A | 109.5 |
C10—C9—H9 | 121.2 | C21—C23—H23B | 109.5 |
C8—C9—H9 | 121.2 | H23A—C23—H23B | 109.5 |
C11—C10—C9 | 121.6 (13) | C21—C23—H23C | 109.5 |
C11—C10—H10 | 119.2 | H23A—C23—H23C | 109.5 |
C9—C10—H10 | 119.2 | H23B—C23—H23C | 109.5 |
C10—C11—C12 | 118.1 (16) | C25—N1—H1A | 109.5 |
C10—C11—C14 | 121.6 (13) | C25—N1—H1B | 109.5 |
C12—C11—C14 | 120.3 (18) | H1A—N1—H1B | 109.5 |
C13—C12—C11 | 120.9 (19) | C25—N1—H1C | 109.5 |
C13—C12—H12 | 119.5 | H1A—N1—H1C | 109.5 |
C11—C12—H12 | 119.5 | H1B—N1—H1C | 109.5 |
C8—C13—C12 | 120.5 (14) | C25—C24—H24A | 109.5 |
C8—C13—H13 | 119.8 | C25—C24—H24B | 109.5 |
C12—C13—H13 | 119.8 | H24A—C24—H24B | 109.5 |
O2—C14—O3 | 125.5 (15) | C25—C24—H24C | 109.5 |
O2—C14—C11 | 118.8 (14) | H24A—C24—H24C | 109.5 |
O3—C14—C11 | 115.5 (18) | H24B—C24—H24C | 109.5 |
C16—C15—C6 | 111.7 (13) | C26—C25—C24 | 116.0 (10) |
C16—C15—C17 | 112.7 (14) | C26—C25—N1 | 110.2 (17) |
C6—C15—C17 | 109.5 (11) | C24—C25—N1 | 107.2 (13) |
C16—C15—H15 | 107.6 | C26—C25—H25 | 107.7 |
C6—C15—H15 | 107.6 | C24—C25—H25 | 107.7 |
C17—C15—H15 | 107.6 | N1—C25—H25 | 107.7 |
C15—C16—H16A | 109.5 | C31—C26—C27 | 118.3 (13) |
C15—C16—H16B | 109.5 | C31—C26—C25 | 121.5 (11) |
H16A—C16—H16B | 109.5 | C27—C26—C25 | 120.2 (12) |
C15—C16—H16C | 109.5 | C26—C27—C28 | 120.7 (15) |
H16A—C16—H16C | 109.5 | C26—C27—H27 | 119.7 |
H16B—C16—H16C | 109.5 | C28—C27—H27 | 119.7 |
C15—C17—H17A | 109.5 | C29—C28—C27 | 116.9 (15) |
C15—C17—H17B | 109.5 | C29—C28—H28 | 121.5 |
H17A—C17—H17B | 109.5 | C27—C28—H28 | 121.5 |
C15—C17—H17C | 109.5 | C28—C29—C30 | 126.1 (15) |
H17A—C17—H17C | 109.5 | C28—C29—H29 | 117.0 |
H17B—C17—H17C | 109.5 | C30—C29—H29 | 117.0 |
C4—C18—C20 | 115.2 (17) | C29—C30—C31 | 114.6 (14) |
C4—C18—C19 | 117 (2) | C29—C30—H30 | 122.7 |
C20—C18—C19 | 109 (2) | C31—C30—H30 | 122.7 |
C4—C18—H18 | 105.1 | C26—C31—C30 | 123.3 (13) |
C20—C18—H18 | 105.1 | C26—C31—H31 | 118.4 |
C19—C18—H18 | 105.1 | C30—C31—H31 | 118.4 |
C31H39NO3 | Dx = 1.238 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.70932 Å |
Orthorhombic, P212121 | Cell parameters from 2405 reflections |
a = 5.9706 (10) Å | θ = 2.4–23.7° |
b = 13.368 (4) Å | µ = 0.08 mm−1 |
c = 31.832 (8) Å | T = 299 K |
V = 2540.7 (11) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.18 × 0.14 mm |
F(000) = 1024 |
Bruker APEX-II CCD diffractometer | Rint = 0.125 |
φ– and ω scans | θmax = 25.0°, θmin = 1.7° |
13548 measured reflections | h = −7→7 |
2324 independent reflections | k = −12→12 |
1279 reflections with I > 2σ(I) | l = −31→31 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.067 | w = 1/[σ2(Fo2) + (0.0772P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.165 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.16 e Å−3 |
2324 reflections | Δρmin = −0.15 e Å−3 |
294 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
0 restraints | Absolute structure parameter: 1.2 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.0504 (13) | 0.2264 (6) | 0.6293 (2) | 0.070 (3) | |
O3 | 0.3045 (11) | 0.6173 (6) | 0.5556 (2) | 0.058 (2) | |
O2 | 0.6120 (11) | 0.6260 (5) | 0.5170 (2) | 0.047 (2) | |
C1 | 0.8206 (16) | 0.2585 (9) | 0.6886 (3) | 0.037 (3) | |
C2 | 0.9036 (14) | 0.3231 (8) | 0.7191 (4) | 0.036 (3) | |
C3 | 0.8433 (15) | 0.3078 (8) | 0.7606 (4) | 0.041 (3) | |
H3 | 0.8998 | 0.3509 | 0.7809 | 0.049* | |
C4 | 0.7036 (15) | 0.2315 (9) | 0.7731 (3) | 0.039 (3) | |
C5 | 0.6222 (14) | 0.1688 (8) | 0.7411 (3) | 0.035 (3) | |
H5 | 0.5271 | 0.1165 | 0.7485 | 0.042* | |
C6 | 0.6772 (15) | 0.1811 (8) | 0.6991 (4) | 0.036 (3) | |
C7 | 0.8952 (17) | 0.2726 (9) | 0.6440 (4) | 0.041 (3) | |
C8 | 0.7852 (14) | 0.3498 (8) | 0.6175 (3) | 0.035 (3)* | |
C9 | 0.8946 (15) | 0.3863 (8) | 0.5827 (3) | 0.039 (3)* | |
H9 | 1.0329 | 0.3600 | 0.5751 | 0.046* | |
C10 | 0.8002 (15) | 0.4618 (8) | 0.5591 (3) | 0.043 (3)* | |
H10 | 0.8748 | 0.4851 | 0.5354 | 0.051* | |
C11 | 0.5938 (14) | 0.5039 (7) | 0.5703 (3) | 0.033 (2)* | |
C12 | 0.4837 (15) | 0.4651 (8) | 0.6047 (3) | 0.040 (3)* | |
H12 | 0.3446 | 0.4905 | 0.6124 | 0.048* | |
C13 | 0.5788 (15) | 0.3884 (8) | 0.6281 (3) | 0.047 (3)* | |
H13 | 0.5024 | 0.3628 | 0.6512 | 0.057* | |
C14 | 0.4986 (18) | 0.5892 (9) | 0.5464 (3) | 0.041 (3) | |
C15 | 1.0523 (15) | 0.4091 (8) | 0.7064 (3) | 0.042 (3) | |
H15 | 1.0815 | 0.4035 | 0.6762 | 0.051* | |
C16 | 1.2788 (14) | 0.4050 (9) | 0.7294 (3) | 0.053 (3) | |
H16A | 1.3376 | 0.3383 | 0.7281 | 0.080* | |
H16B | 1.2583 | 0.4239 | 0.7583 | 0.080* | |
H16C | 1.3819 | 0.4504 | 0.7163 | 0.080* | |
C17 | 0.9363 (18) | 0.5088 (9) | 0.7142 (4) | 0.072 (4) | |
H17A | 0.9213 | 0.5196 | 0.7439 | 0.108* | |
H17B | 0.7906 | 0.5080 | 0.7015 | 0.108* | |
H17C | 1.0239 | 0.5618 | 0.7022 | 0.108* | |
C18 | 0.6388 (17) | 0.2105 (10) | 0.8184 (4) | 0.055 (3) | |
H18 | 0.6513 | 0.1378 | 0.8215 | 0.066* | |
C19 | 0.7932 (17) | 0.2533 (9) | 0.8512 (4) | 0.069 (4) | |
H19A | 0.7776 | 0.3248 | 0.8518 | 0.103* | |
H19B | 0.9451 | 0.2362 | 0.8444 | 0.103* | |
H19C | 0.7552 | 0.2263 | 0.8782 | 0.103* | |
C20 | 0.3991 (17) | 0.2334 (10) | 0.8265 (4) | 0.083 (5) | |
H20A | 0.3546 | 0.2039 | 0.8527 | 0.124* | |
H20B | 0.3091 | 0.2065 | 0.8042 | 0.124* | |
H20C | 0.3789 | 0.3046 | 0.8279 | 0.124* | |
C21 | 0.5905 (16) | 0.1083 (8) | 0.6663 (3) | 0.042 (3) | |
H21 | 0.5639 | 0.1472 | 0.6407 | 0.050* | |
C22 | 0.7669 (18) | 0.0298 (9) | 0.6555 (4) | 0.063 (3) | |
H22A | 0.7993 | −0.0097 | 0.6799 | 0.095* | |
H22B | 0.9011 | 0.0625 | 0.6461 | 0.095* | |
H22C | 0.7112 | −0.0127 | 0.6335 | 0.095* | |
C23 | 0.3696 (15) | 0.0596 (9) | 0.6778 (4) | 0.064 (4) | |
H23A | 0.2684 | 0.1095 | 0.6883 | 0.096* | |
H23B | 0.3944 | 0.0100 | 0.6991 | 0.096* | |
H23C | 0.3062 | 0.0285 | 0.6534 | 0.096* | |
N1 | 0.0383 (13) | 0.6720 (6) | 0.4902 (3) | 0.042 (2) | |
H1A | 0.1410 | 0.6507 | 0.5084 | 0.051* | |
H1B | −0.0969 | 0.6529 | 0.4988 | 0.051* | |
H1C | 0.0432 | 0.7384 | 0.4886 | 0.051* | |
C24 | 0.3050 (15) | 0.6681 (8) | 0.4309 (4) | 0.052 (3) | |
H24A | 0.4236 | 0.6510 | 0.4500 | 0.077* | |
H24B | 0.2958 | 0.7396 | 0.4284 | 0.077* | |
H24C | 0.3348 | 0.6393 | 0.4039 | 0.077* | |
C25 | 0.0849 (16) | 0.6279 (10) | 0.4477 (3) | 0.044 (3) | |
H25 | −0.0332 | 0.6516 | 0.4288 | 0.053* | |
C26 | 0.0631 (17) | 0.5163 (9) | 0.4502 (3) | 0.041 (3) | |
C27 | −0.1340 (16) | 0.4684 (10) | 0.4401 (3) | 0.048 (3) | |
H27 | −0.2561 | 0.5062 | 0.4314 | 0.058* | |
C28 | −0.154 (2) | 0.3681 (13) | 0.4425 (4) | 0.068 (4) | |
H28 | −0.2886 | 0.3379 | 0.4347 | 0.081* | |
C29 | 0.022 (3) | 0.3094 (10) | 0.4564 (4) | 0.065 (4) | |
H29 | 0.0077 | 0.2403 | 0.4580 | 0.078* | |
C30 | 0.218 (2) | 0.3556 (12) | 0.4679 (4) | 0.066 (4) | |
H30 | 0.3385 | 0.3177 | 0.4775 | 0.079* | |
C31 | 0.2369 (19) | 0.4591 (11) | 0.4652 (3) | 0.052 (3) | |
H31 | 0.3689 | 0.4901 | 0.4736 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.082 (5) | 0.066 (8) | 0.062 (7) | 0.043 (6) | 0.027 (5) | 0.024 (4) |
O3 | 0.050 (4) | 0.055 (7) | 0.068 (7) | 0.023 (4) | 0.007 (4) | 0.016 (4) |
O2 | 0.056 (4) | 0.036 (7) | 0.048 (6) | −0.004 (4) | 0.007 (4) | 0.017 (3) |
C1 | 0.045 (6) | 0.028 (12) | 0.037 (10) | 0.007 (6) | 0.009 (6) | 0.011 (5) |
C2 | 0.039 (6) | 0.023 (11) | 0.048 (11) | 0.006 (6) | 0.004 (6) | 0.005 (5) |
C3 | 0.040 (6) | 0.044 (12) | 0.039 (11) | −0.004 (6) | −0.004 (6) | −0.003 (5) |
C4 | 0.041 (6) | 0.042 (12) | 0.032 (11) | 0.004 (6) | −0.005 (6) | −0.003 (5) |
C5 | 0.034 (5) | 0.032 (12) | 0.038 (11) | −0.005 (5) | 0.003 (5) | 0.007 (5) |
C6 | 0.041 (6) | 0.029 (11) | 0.037 (11) | 0.000 (6) | 0.003 (6) | 0.008 (4) |
C7 | 0.047 (6) | 0.020 (10) | 0.057 (11) | 0.000 (6) | −0.004 (6) | 0.005 (5) |
C14 | 0.055 (7) | 0.033 (11) | 0.033 (9) | 0.001 (7) | −0.016 (6) | 0.003 (5) |
C15 | 0.043 (6) | 0.037 (10) | 0.047 (9) | −0.005 (6) | 0.004 (5) | −0.002 (5) |
C16 | 0.046 (6) | 0.055 (12) | 0.058 (11) | 0.001 (6) | −0.003 (6) | 0.002 (5) |
C17 | 0.048 (6) | 0.049 (14) | 0.119 (14) | −0.007 (7) | 0.006 (7) | 0.013 (6) |
C18 | 0.063 (7) | 0.072 (12) | 0.030 (11) | −0.002 (7) | 0.010 (6) | 0.003 (5) |
C19 | 0.062 (7) | 0.102 (14) | 0.042 (11) | −0.017 (8) | −0.009 (7) | −0.004 (6) |
C20 | 0.058 (8) | 0.107 (16) | 0.082 (14) | −0.014 (8) | 0.016 (7) | −0.009 (7) |
C21 | 0.064 (7) | 0.048 (11) | 0.013 (9) | −0.002 (7) | −0.004 (6) | −0.005 (4) |
C22 | 0.079 (7) | 0.049 (11) | 0.063 (11) | 0.007 (7) | 0.005 (7) | −0.020 (5) |
C23 | 0.057 (7) | 0.053 (12) | 0.081 (12) | −0.021 (7) | −0.017 (7) | 0.003 (5) |
N1 | 0.039 (4) | 0.030 (8) | 0.058 (9) | 0.004 (4) | −0.005 (4) | 0.002 (4) |
C24 | 0.062 (7) | 0.036 (10) | 0.057 (10) | −0.008 (6) | 0.015 (6) | 0.002 (5) |
C25 | 0.056 (7) | 0.046 (12) | 0.030 (10) | 0.009 (7) | −0.008 (6) | 0.000 (5) |
C26 | 0.050 (7) | 0.055 (12) | 0.019 (9) | −0.008 (8) | 0.002 (6) | 0.000 (4) |
C27 | 0.050 (7) | 0.059 (12) | 0.036 (11) | −0.017 (7) | 0.004 (6) | −0.001 (5) |
C28 | 0.079 (9) | 0.065 (15) | 0.060 (12) | −0.025 (10) | 0.013 (7) | −0.017 (6) |
C29 | 0.107 (11) | 0.040 (13) | 0.049 (11) | −0.015 (10) | 0.032 (8) | −0.012 (6) |
C30 | 0.071 (9) | 0.056 (15) | 0.072 (13) | 0.005 (9) | 0.009 (7) | 0.007 (6) |
C31 | 0.058 (7) | 0.049 (13) | 0.049 (12) | −0.006 (8) | 0.002 (6) | 0.002 (5) |
O1—C7 | 1.208 (12) | C18—H18 | 0.9800 |
O3—C14 | 1.253 (12) | C19—H19A | 0.9600 |
O2—C14 | 1.254 (11) | C19—H19B | 0.9600 |
C1—C6 | 1.385 (14) | C19—H19C | 0.9600 |
C1—C2 | 1.390 (15) | C20—H20A | 0.9600 |
C1—C7 | 1.499 (14) | C20—H20B | 0.9600 |
C2—C3 | 1.386 (13) | C20—H20C | 0.9600 |
C2—C15 | 1.507 (14) | C21—C23 | 1.515 (13) |
C3—C4 | 1.376 (14) | C21—C22 | 1.526 (13) |
C3—H3 | 0.9300 | C21—H21 | 0.9800 |
C4—C5 | 1.406 (14) | C22—H22A | 0.9600 |
C4—C18 | 1.518 (15) | C22—H22B | 0.9600 |
C5—C6 | 1.386 (13) | C22—H22C | 0.9600 |
C5—H5 | 0.9300 | C23—H23A | 0.9600 |
C6—C21 | 1.517 (14) | C23—H23B | 0.9600 |
C7—C8 | 1.485 (15) | C23—H23C | 0.9600 |
C8—C9 | 1.374 (12) | N1—C25 | 1.503 (13) |
C8—C13 | 1.379 (13) | N1—H1A | 0.8900 |
C9—C10 | 1.379 (13) | N1—H1B | 0.8900 |
C9—H9 | 0.9300 | N1—H1C | 0.8900 |
C10—C11 | 1.401 (11) | C24—C25 | 1.516 (13) |
C10—H10 | 0.9300 | C24—H24A | 0.9600 |
C11—C12 | 1.380 (12) | C24—H24B | 0.9600 |
C11—C14 | 1.484 (13) | C24—H24C | 0.9600 |
C12—C13 | 1.388 (13) | C25—C26 | 1.500 (14) |
C12—H12 | 0.9300 | C25—H25 | 0.9800 |
C13—H13 | 0.9300 | C26—C31 | 1.374 (13) |
C15—C17 | 1.522 (14) | C26—C27 | 1.378 (13) |
C15—C16 | 1.539 (12) | C27—C28 | 1.349 (15) |
C15—H15 | 0.9800 | C27—H27 | 0.9300 |
C16—H16A | 0.9600 | C28—C29 | 1.386 (17) |
C16—H16B | 0.9600 | C28—H28 | 0.9300 |
C16—H16C | 0.9600 | C29—C30 | 1.375 (16) |
C17—H17A | 0.9600 | C29—H29 | 0.9300 |
C17—H17B | 0.9600 | C30—C31 | 1.390 (15) |
C17—H17C | 0.9600 | C30—H30 | 0.9300 |
C18—C20 | 1.486 (13) | C31—H31 | 0.9300 |
C18—C19 | 1.506 (14) | ||
C6—C1—C2 | 121.0 (11) | C18—C19—H19A | 109.5 |
C6—C1—C7 | 120.5 (9) | C18—C19—H19B | 109.5 |
C2—C1—C7 | 118.5 (11) | H19A—C19—H19B | 109.5 |
C3—C2—C1 | 118.8 (11) | C18—C19—H19C | 109.5 |
C3—C2—C15 | 121.3 (9) | H19A—C19—H19C | 109.5 |
C1—C2—C15 | 119.8 (11) | H19B—C19—H19C | 109.5 |
C4—C3—C2 | 122.9 (10) | C18—C20—H20A | 109.5 |
C4—C3—H3 | 118.6 | C18—C20—H20B | 109.5 |
C2—C3—H3 | 118.6 | H20A—C20—H20B | 109.5 |
C3—C4—C5 | 116.2 (11) | C18—C20—H20C | 109.5 |
C3—C4—C18 | 124.5 (10) | H20A—C20—H20C | 109.5 |
C5—C4—C18 | 119.3 (11) | H20B—C20—H20C | 109.5 |
C6—C5—C4 | 123.1 (11) | C23—C21—C6 | 113.9 (9) |
C6—C5—H5 | 118.5 | C23—C21—C22 | 111.1 (10) |
C4—C5—H5 | 118.5 | C6—C21—C22 | 111.2 (8) |
C1—C6—C5 | 118.0 (10) | C23—C21—H21 | 106.7 |
C1—C6—C21 | 121.5 (11) | C6—C21—H21 | 106.7 |
C5—C6—C21 | 120.4 (10) | C22—C21—H21 | 106.7 |
O1—C7—C8 | 118.4 (11) | C21—C22—H22A | 109.5 |
O1—C7—C1 | 121.9 (10) | C21—C22—H22B | 109.5 |
C8—C7—C1 | 119.6 (10) | H22A—C22—H22B | 109.5 |
C9—C8—C13 | 119.3 (10) | C21—C22—H22C | 109.5 |
C9—C8—C7 | 119.6 (8) | H22A—C22—H22C | 109.5 |
C13—C8—C7 | 121.1 (10) | H22B—C22—H22C | 109.5 |
C8—C9—C10 | 120.3 (9) | C21—C23—H23A | 109.5 |
C8—C9—H9 | 119.8 | C21—C23—H23B | 109.5 |
C10—C9—H9 | 119.8 | H23A—C23—H23B | 109.5 |
C9—C10—C11 | 121.0 (10) | C21—C23—H23C | 109.5 |
C9—C10—H10 | 119.5 | H23A—C23—H23C | 109.5 |
C11—C10—H10 | 119.5 | H23B—C23—H23C | 109.5 |
C12—C11—C10 | 118.0 (9) | C25—N1—H1A | 109.5 |
C12—C11—C14 | 120.9 (9) | C25—N1—H1B | 109.5 |
C10—C11—C14 | 121.0 (10) | H1A—N1—H1B | 109.5 |
C11—C12—C13 | 120.6 (9) | C25—N1—H1C | 109.5 |
C11—C12—H12 | 119.7 | H1A—N1—H1C | 109.5 |
C13—C12—H12 | 119.7 | H1B—N1—H1C | 109.5 |
C8—C13—C12 | 120.7 (10) | C25—C24—H24A | 109.5 |
C8—C13—H13 | 119.6 | C25—C24—H24B | 109.5 |
C12—C13—H13 | 119.6 | H24A—C24—H24B | 109.5 |
O3—C14—O2 | 123.8 (10) | C25—C24—H24C | 109.5 |
O3—C14—C11 | 117.6 (10) | H24A—C24—H24C | 109.5 |
O2—C14—C11 | 118.5 (9) | H24B—C24—H24C | 109.5 |
C2—C15—C17 | 110.9 (8) | C26—C25—N1 | 109.0 (8) |
C2—C15—C16 | 111.3 (8) | C26—C25—C24 | 116.6 (9) |
C17—C15—C16 | 110.7 (9) | N1—C25—C24 | 109.7 (9) |
C2—C15—H15 | 107.9 | C26—C25—H25 | 107.0 |
C17—C15—H15 | 107.9 | N1—C25—H25 | 107.0 |
C16—C15—H15 | 107.9 | C24—C25—H25 | 107.0 |
C15—C16—H16A | 109.5 | C31—C26—C27 | 117.9 (12) |
C15—C16—H16B | 109.5 | C31—C26—C25 | 120.5 (10) |
H16A—C16—H16B | 109.5 | C27—C26—C25 | 121.6 (11) |
C15—C16—H16C | 109.5 | C28—C27—C26 | 121.8 (12) |
H16A—C16—H16C | 109.5 | C28—C27—H27 | 119.1 |
H16B—C16—H16C | 109.5 | C26—C27—H27 | 119.1 |
C15—C17—H17A | 109.5 | C27—C28—C29 | 120.8 (12) |
C15—C17—H17B | 109.5 | C27—C28—H28 | 119.6 |
H17A—C17—H17B | 109.5 | C29—C28—H28 | 119.6 |
C15—C17—H17C | 109.5 | C30—C29—C28 | 118.6 (13) |
H17A—C17—H17C | 109.5 | C30—C29—H29 | 120.7 |
H17B—C17—H17C | 109.5 | C28—C29—H29 | 120.7 |
C20—C18—C19 | 113.0 (10) | C29—C30—C31 | 119.9 (13) |
C20—C18—C4 | 111.9 (10) | C29—C30—H30 | 120.1 |
C19—C18—C4 | 115.6 (9) | C31—C30—H30 | 120.1 |
C20—C18—H18 | 105.1 | C26—C31—C30 | 121.0 (11) |
C19—C18—H18 | 105.1 | C26—C31—H31 | 119.5 |
C4—C18—H18 | 105.1 | C30—C31—H31 | 119.5 |
C31H39NO3 | Dx = 1.238 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.70932 Å |
Orthorhombic, P212121 | Cell parameters from 2531 reflections |
a = 5.9793 (10) Å | θ = 2.4–23.8° |
b = 13.334 (4) Å | µ = 0.08 mm−1 |
c = 31.884 (8) Å | T = 299 K |
V = 2542.0 (11) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.18 × 0.14 mm |
F(000) = 1024 |
Bruker APEX-II CCD diffractometer | Rint = 0.132 |
φ– and ω scans | θmax = 25.4°, θmin = 1.7° |
13624 measured reflections | h = −7→7 |
2378 independent reflections | k = −13→12 |
1201 reflections with I > 2σ(I) | l = −31→31 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.069 | w = 1/[σ2(Fo2) + (0.0914P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.189 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.17 e Å−3 |
2378 reflections | Δρmin = −0.19 e Å−3 |
278 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
74 restraints | Absolute structure parameter: −0.9 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O2 | 0.3867 (11) | 0.6251 (6) | 0.4830 (2) | 0.053 (2) | |
O3 | 0.6941 (13) | 0.6172 (6) | 0.4450 (3) | 0.068 (2) | |
N1 | 0.9607 (14) | 0.6719 (7) | 0.5097 (3) | 0.048 (3) | |
H1A | 0.9639 | 0.7384 | 0.5122 | 0.058* | |
H1B | 0.8527 | 0.6544 | 0.4919 | 0.058* | |
H1C | 1.0917 | 0.6503 | 0.5000 | 0.058* | |
C1 | 0.1780 (16) | 0.2605 (9) | 0.3109 (3) | 0.042 (3)* | |
C2 | 0.0987 (15) | 0.3230 (9) | 0.2798 (3) | 0.043 (3)* | |
C3 | 0.1591 (15) | 0.3072 (8) | 0.2386 (4) | 0.047 (3)* | |
H3 | 0.1021 | 0.3497 | 0.2181 | 0.056* | |
C4 | 0.2993 (15) | 0.2317 (9) | 0.2269 (3) | 0.043 (3)* | |
C5 | 0.3816 (14) | 0.1679 (8) | 0.2585 (3) | 0.041 (3)* | |
H5 | 0.4760 | 0.1152 | 0.2513 | 0.049* | |
C6 | 0.3248 (15) | 0.1820 (8) | 0.3002 (3) | 0.038 (3)* | |
C8 | 0.2118 (16) | 0.3497 (8) | 0.3820 (3) | 0.042 (3)* | |
C9 | 0.1047 (17) | 0.3868 (8) | 0.4162 (3) | 0.045 (3)* | |
H9 | −0.0344 | 0.3609 | 0.4234 | 0.054* | |
C10 | 0.1968 (17) | 0.4620 (9) | 0.4404 (3) | 0.051 (3)* | |
H10 | 0.1215 | 0.4849 | 0.4641 | 0.061* | |
C11 | 0.4032 (16) | 0.5036 (8) | 0.4294 (3) | 0.041 (3)* | |
C12 | 0.5145 (17) | 0.4637 (8) | 0.3952 (3) | 0.044 (3)* | |
H12 | 0.6570 | 0.4867 | 0.3886 | 0.053* | |
C13 | 0.4178 (16) | 0.3911 (9) | 0.3711 (3) | 0.051 (3)* | |
H13 | 0.4904 | 0.3690 | 0.3470 | 0.062* | |
C14 | 0.498 (2) | 0.5878 (9) | 0.4539 (4) | 0.041 (3) | |
C15 | −0.0501 (17) | 0.4111 (8) | 0.2922 (3) | 0.047 (3) | |
H15 | −0.0767 | 0.4060 | 0.3225 | 0.057* | |
C16 | −0.2773 (15) | 0.4039 (9) | 0.2706 (3) | 0.056 (3) | |
H16A | −0.3434 | 0.3398 | 0.2766 | 0.084* | |
H16B | −0.3734 | 0.4562 | 0.2808 | 0.084* | |
H16C | −0.2581 | 0.4110 | 0.2408 | 0.084* | |
C17 | 0.0656 (19) | 0.5091 (9) | 0.2846 (4) | 0.073 (4) | |
H17A | −0.0312 | 0.5632 | 0.2926 | 0.109* | |
H17B | 0.2005 | 0.5119 | 0.3009 | 0.109* | |
H17C | 0.1018 | 0.5150 | 0.2554 | 0.109* | |
C18 | 0.3640 (18) | 0.2084 (10) | 0.1812 (4) | 0.061 (4) | |
H18 | 0.3547 | 0.1354 | 0.1785 | 0.073* | |
C19 | 0.2069 (19) | 0.2501 (10) | 0.1488 (4) | 0.077 (4) | |
H19A | 0.0565 | 0.2304 | 0.1554 | 0.115* | |
H19B | 0.2171 | 0.3219 | 0.1486 | 0.115* | |
H19C | 0.2467 | 0.2244 | 0.1216 | 0.115* | |
C20 | 0.6052 (18) | 0.2345 (12) | 0.1740 (4) | 0.090 (5) | |
H20A | 0.6949 | 0.2055 | 0.1959 | 0.135* | |
H20B | 0.6523 | 0.2085 | 0.1474 | 0.135* | |
H20C | 0.6227 | 0.3060 | 0.1743 | 0.135* | |
C24 | 0.6962 (17) | 0.6666 (8) | 0.5685 (4) | 0.058 (3) | |
H24A | 0.7002 | 0.7385 | 0.5686 | 0.087* | |
H24B | 0.5752 | 0.6439 | 0.5511 | 0.087* | |
H24C | 0.6743 | 0.6427 | 0.5966 | 0.087* | |
C25 | 0.9166 (18) | 0.6260 (11) | 0.5515 (4) | 0.056 (4) | |
H25 | 1.0346 | 0.6499 | 0.5703 | 0.067* | |
C26 | 0.939 (2) | 0.5150 (10) | 0.5492 (3) | 0.045 (3) | |
C27 | 0.763 (2) | 0.4569 (12) | 0.5347 (4) | 0.062 (4) | |
H27 | 0.6289 | 0.4870 | 0.5267 | 0.074* | |
C28 | 0.787 (3) | 0.3547 (13) | 0.5323 (4) | 0.076 (4) | |
H28 | 0.6684 | 0.3155 | 0.5227 | 0.092* | |
C29 | 0.984 (3) | 0.3100 (11) | 0.5439 (5) | 0.076 (4) | |
H29 | 0.9970 | 0.2407 | 0.5422 | 0.091* | |
C30 | 1.157 (2) | 0.3644 (14) | 0.5577 (4) | 0.072 (4) | |
H30 | 1.2904 | 0.3333 | 0.5655 | 0.087* | |
C31 | 1.1351 (18) | 0.4671 (12) | 0.5602 (4) | 0.058 (4) | |
H31 | 1.2556 | 0.5052 | 0.5695 | 0.070* | |
O1 | −0.0561 (17) | 0.2284 (8) | 0.3694 (3) | 0.079 (4) | 0.931 (14) |
C7 | 0.102 (2) | 0.2744 (10) | 0.3553 (3) | 0.047 (3) | 0.931 (14) |
C21 | 0.4059 (19) | 0.1084 (10) | 0.3338 (4) | 0.050 (4) | 0.931 (14) |
H21 | 0.4328 | 0.1476 | 0.3593 | 0.060* | 0.931 (14) |
C22 | 0.229 (2) | 0.0306 (10) | 0.3445 (4) | 0.074 (4) | 0.931 (14) |
H22A | 0.0916 | 0.0638 | 0.3516 | 0.110* | 0.931 (14) |
H22B | 0.2052 | −0.0124 | 0.3208 | 0.110* | 0.931 (14) |
H22C | 0.2785 | −0.0087 | 0.3680 | 0.110* | 0.931 (14) |
C23 | 0.6255 (19) | 0.0578 (10) | 0.3225 (4) | 0.068 (4) | 0.931 (14) |
H23A | 0.7350 | 0.1080 | 0.3158 | 0.102* | 0.931 (14) |
H23B | 0.6767 | 0.0187 | 0.3458 | 0.102* | 0.931 (14) |
H23C | 0.6034 | 0.0149 | 0.2987 | 0.102* | 0.931 (14) |
O1D | −0.120 (8) | 0.259 (8) | 0.364 (3) | 0.076 (17)* | 0.069 (14) |
C7D | 0.119 (8) | 0.258 (3) | 0.3585 (8) | 0.051 (16)* | 0.069 (14) |
C21D | 0.413 (15) | 0.132 (6) | 0.3406 (12) | 0.052 (16)* | 0.069 (14) |
H21D | 0.5498 | 0.1673 | 0.3489 | 0.063* | 0.069 (14) |
C22D | 0.229 (17) | 0.160 (4) | 0.3720 (18) | 0.06 (3)* | 0.069 (14) |
H22D | 0.1183 | 0.1072 | 0.3731 | 0.076* | 0.069 (14) |
H22E | 0.2935 | 0.1678 | 0.3997 | 0.076* | 0.069 (14) |
C23D | 0.47 (3) | 0.023 (7) | 0.336 (3) | 0.08 (3)* | 0.069 (14) |
H23E | 0.5834 | 0.0146 | 0.3157 | 0.117* | 0.069 (14) |
H23D | 0.5157 | −0.0033 | 0.3626 | 0.117* | 0.069 (14) |
H23F | 0.3357 | −0.0128 | 0.3271 | 0.117* | 0.069 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.058 (4) | 0.048 (7) | 0.052 (7) | 0.004 (4) | 0.003 (4) | −0.024 (4) |
O3 | 0.054 (4) | 0.070 (8) | 0.081 (8) | −0.027 (5) | 0.009 (5) | −0.014 (4) |
N1 | 0.047 (5) | 0.038 (9) | 0.059 (9) | −0.011 (5) | −0.005 (5) | −0.003 (4) |
C14 | 0.062 (7) | 0.017 (10) | 0.046 (10) | 0.006 (7) | −0.016 (7) | −0.008 (5) |
C15 | 0.055 (7) | 0.033 (10) | 0.055 (10) | 0.011 (7) | 0.009 (6) | 0.000 (5) |
C16 | 0.052 (6) | 0.047 (12) | 0.069 (11) | 0.001 (6) | 0.003 (7) | 0.002 (5) |
C17 | 0.058 (6) | 0.029 (13) | 0.132 (14) | −0.006 (7) | 0.008 (7) | −0.013 (6) |
C18 | 0.064 (8) | 0.068 (12) | 0.050 (12) | −0.007 (7) | 0.009 (7) | −0.003 (6) |
C19 | 0.074 (8) | 0.115 (15) | 0.042 (11) | 0.021 (9) | −0.001 (8) | 0.001 (6) |
C20 | 0.069 (9) | 0.147 (18) | 0.054 (13) | 0.019 (9) | 0.023 (7) | 0.009 (7) |
C24 | 0.074 (8) | 0.048 (11) | 0.053 (11) | 0.008 (7) | 0.021 (7) | −0.002 (5) |
C25 | 0.063 (8) | 0.091 (15) | 0.014 (11) | −0.009 (8) | −0.007 (6) | 0.000 (6) |
C26 | 0.065 (8) | 0.052 (12) | 0.018 (10) | 0.003 (8) | 0.010 (6) | 0.001 (5) |
C27 | 0.070 (9) | 0.047 (14) | 0.068 (14) | 0.000 (9) | −0.005 (8) | 0.002 (6) |
C28 | 0.085 (11) | 0.039 (16) | 0.105 (16) | −0.016 (10) | 0.000 (9) | −0.001 (7) |
C29 | 0.111 (12) | 0.037 (13) | 0.080 (13) | 0.010 (11) | 0.036 (10) | 0.011 (7) |
C30 | 0.075 (10) | 0.070 (17) | 0.072 (14) | 0.032 (11) | 0.009 (8) | 0.020 (7) |
C31 | 0.045 (8) | 0.078 (15) | 0.052 (13) | 0.023 (8) | 0.008 (6) | 0.007 (6) |
O1 | 0.087 (6) | 0.076 (10) | 0.075 (9) | −0.041 (7) | 0.033 (6) | −0.030 (5) |
C7 | 0.057 (7) | 0.034 (11) | 0.050 (11) | −0.002 (7) | −0.001 (7) | −0.005 (5) |
C21 | 0.061 (8) | 0.063 (12) | 0.025 (10) | 0.013 (8) | −0.005 (6) | −0.001 (5) |
C22 | 0.102 (10) | 0.059 (13) | 0.059 (12) | −0.017 (9) | −0.002 (8) | 0.016 (6) |
C23 | 0.069 (9) | 0.067 (13) | 0.068 (13) | 0.011 (8) | −0.017 (8) | 0.002 (6) |
O2—C14 | 1.245 (11) | C18—H18 | 0.9800 |
O3—C14 | 1.269 (12) | C19—H19A | 0.9600 |
N1—C25 | 1.489 (14) | C19—H19B | 0.9600 |
N1—H1A | 0.8900 | C19—H19C | 0.9600 |
N1—H1B | 0.8900 | C20—H20A | 0.9600 |
N1—H1C | 0.8900 | C20—H20B | 0.9600 |
C1—C2 | 1.377 (14) | C20—H20C | 0.9600 |
C1—C6 | 1.408 (13) | C24—C25 | 1.525 (14) |
C1—C7 | 1.498 (13) | C24—H24A | 0.9600 |
C1—C7D | 1.56 (2) | C24—H24B | 0.9600 |
C2—C3 | 1.380 (13) | C24—H24C | 0.9600 |
C2—C15 | 1.526 (14) | C25—C26 | 1.488 (15) |
C3—C4 | 1.363 (13) | C25—H25 | 0.9800 |
C3—H3 | 0.9300 | C26—C31 | 1.381 (15) |
C4—C5 | 1.409 (14) | C26—C27 | 1.388 (15) |
C4—C18 | 1.538 (15) | C27—C28 | 1.372 (17) |
C5—C6 | 1.384 (13) | C27—H27 | 0.9300 |
C5—H5 | 0.9300 | C28—C29 | 1.371 (18) |
C6—C21 | 1.531 (13) | C28—H28 | 0.9300 |
C6—C21D | 1.54 (3) | C29—C30 | 1.342 (18) |
C8—C9 | 1.356 (12) | C29—H29 | 0.9300 |
C8—C13 | 1.394 (13) | C30—C31 | 1.379 (16) |
C8—C7 | 1.471 (14) | C30—H30 | 0.9300 |
C8—C7D | 1.54 (2) | C31—H31 | 0.9300 |
C9—C10 | 1.381 (14) | O1—C7 | 1.215 (12) |
C9—H9 | 0.9300 | C21—C23 | 1.519 (14) |
C10—C11 | 1.398 (12) | C21—C22 | 1.520 (14) |
C10—H10 | 0.9300 | C21—H21 | 0.9800 |
C11—C12 | 1.384 (13) | C22—H22A | 0.9600 |
C11—C14 | 1.481 (14) | C22—H22B | 0.9600 |
C12—C13 | 1.364 (14) | C22—H22C | 0.9600 |
C12—H12 | 0.9300 | C23—H23A | 0.9600 |
C13—H13 | 0.9300 | C23—H23B | 0.9600 |
C15—C17 | 1.498 (15) | C23—H23C | 0.9600 |
C15—C16 | 1.527 (13) | O1D—C7D | 1.44 (3) |
C15—H15 | 0.9800 | C7D—C22D | 1.53 (3) |
C16—H16A | 0.9600 | C21D—C23D | 1.50 (3) |
C16—H16B | 0.9600 | C21D—C22D | 1.53 (3) |
C16—H16C | 0.9600 | C21D—H21D | 0.9800 |
C17—H17A | 0.9600 | C22D—H22D | 0.9700 |
C17—H17B | 0.9600 | C22D—H22E | 0.9700 |
C17—H17C | 0.9600 | C23D—H23E | 0.9600 |
C18—C20 | 1.501 (14) | C23D—H23D | 0.9600 |
C18—C19 | 1.503 (15) | C23D—H23F | 0.9600 |
C25—N1—H1A | 109.5 | C18—C20—H20A | 109.5 |
C25—N1—H1B | 109.5 | C18—C20—H20B | 109.5 |
H1A—N1—H1B | 109.5 | H20A—C20—H20B | 109.5 |
C25—N1—H1C | 109.5 | C18—C20—H20C | 109.5 |
H1A—N1—H1C | 109.5 | H20A—C20—H20C | 109.5 |
H1B—N1—H1C | 109.5 | H20B—C20—H20C | 109.5 |
C2—C1—C6 | 119.4 (10) | C25—C24—H24A | 109.5 |
C2—C1—C7 | 120.0 (11) | C25—C24—H24B | 109.5 |
C6—C1—C7 | 120.5 (9) | H24A—C24—H24B | 109.5 |
C2—C1—C7D | 129 (2) | C25—C24—H24C | 109.5 |
C6—C1—C7D | 111 (2) | H24A—C24—H24C | 109.5 |
C1—C2—C3 | 120.2 (11) | H24B—C24—H24C | 109.5 |
C1—C2—C15 | 118.7 (10) | C26—C25—N1 | 110.5 (9) |
C3—C2—C15 | 121.1 (9) | C26—C25—C24 | 116.5 (10) |
C4—C3—C2 | 122.3 (10) | N1—C25—C24 | 109.0 (10) |
C4—C3—H3 | 118.8 | C26—C25—H25 | 106.7 |
C2—C3—H3 | 118.8 | N1—C25—H25 | 106.7 |
C3—C4—C5 | 117.7 (11) | C24—C25—H25 | 106.7 |
C3—C4—C18 | 124.3 (10) | C31—C26—C27 | 118.1 (13) |
C5—C4—C18 | 118.0 (10) | C31—C26—C25 | 121.6 (12) |
C6—C5—C4 | 121.4 (11) | C27—C26—C25 | 120.2 (12) |
C6—C5—H5 | 119.3 | C28—C27—C26 | 119.6 (13) |
C4—C5—H5 | 119.3 | C28—C27—H27 | 120.2 |
C5—C6—C1 | 119.0 (8) | C26—C27—H27 | 120.2 |
C5—C6—C21 | 120.5 (10) | C29—C28—C27 | 120.4 (14) |
C1—C6—C21 | 120.3 (10) | C29—C28—H28 | 119.8 |
C5—C6—C21D | 131 (2) | C27—C28—H28 | 119.8 |
C1—C6—C21D | 109 (2) | C30—C29—C28 | 121.3 (15) |
C9—C8—C13 | 118.2 (10) | C30—C29—H29 | 119.3 |
C9—C8—C7 | 120.3 (9) | C28—C29—H29 | 119.3 |
C13—C8—C7 | 121.2 (11) | C29—C30—C31 | 118.7 (13) |
C9—C8—C7D | 120.7 (16) | C29—C30—H30 | 120.7 |
C13—C8—C7D | 120.8 (17) | C31—C30—H30 | 120.6 |
C8—C9—C10 | 121.7 (10) | C30—C31—C26 | 121.8 (13) |
C8—C9—H9 | 119.1 | C30—C31—H31 | 119.1 |
C10—C9—H9 | 119.1 | C26—C31—H31 | 119.1 |
C9—C10—C11 | 120.0 (11) | O1—C7—C8 | 118.5 (11) |
C9—C10—H10 | 120.0 | O1—C7—C1 | 121.5 (10) |
C11—C10—H10 | 120.0 | C8—C7—C1 | 119.9 (10) |
C12—C11—C10 | 118.0 (10) | C23—C21—C22 | 110.6 (11) |
C12—C11—C14 | 121.6 (9) | C23—C21—C6 | 113.1 (10) |
C10—C11—C14 | 120.4 (10) | C22—C21—C6 | 112.0 (9) |
C13—C12—C11 | 120.8 (9) | C23—C21—H21 | 106.9 |
C13—C12—H12 | 119.6 | C22—C21—H21 | 106.9 |
C11—C12—H12 | 119.6 | C6—C21—H21 | 106.9 |
C12—C13—C8 | 121.0 (11) | C21—C22—H22A | 109.5 |
C12—C13—H13 | 119.5 | C21—C22—H22B | 109.5 |
C8—C13—H13 | 119.5 | H22A—C22—H22B | 109.5 |
O2—C14—O3 | 122.6 (10) | C21—C22—H22C | 109.5 |
O2—C14—C11 | 119.5 (10) | H22A—C22—H22C | 109.5 |
O3—C14—C11 | 118.0 (10) | H22B—C22—H22C | 109.5 |
C17—C15—C2 | 111.1 (8) | C21—C23—H23A | 109.5 |
C17—C15—C16 | 113.1 (9) | C21—C23—H23B | 109.5 |
C2—C15—C16 | 110.7 (9) | H23A—C23—H23B | 109.5 |
C17—C15—H15 | 107.2 | C21—C23—H23C | 109.5 |
C2—C15—H15 | 107.2 | H23A—C23—H23C | 109.5 |
C16—C15—H15 | 107.2 | H23B—C23—H23C | 109.5 |
C15—C16—H16A | 109.5 | O1D—C7D—C22D | 114 (4) |
C15—C16—H16B | 109.5 | O1D—C7D—C8 | 107 (3) |
H16A—C16—H16B | 109.5 | C22D—C7D—C8 | 113 (3) |
C15—C16—H16C | 109.5 | O1D—C7D—C1 | 110 (4) |
H16A—C16—H16C | 109.5 | C22D—C7D—C1 | 101 (3) |
H16B—C16—H16C | 109.5 | C8—C7D—C1 | 112.2 (19) |
C15—C17—H17A | 109.5 | C23D—C21D—C22D | 117 (5) |
C15—C17—H17B | 109.5 | C23D—C21D—C6 | 114 (4) |
H17A—C17—H17B | 109.5 | C22D—C21D—C6 | 101 (3) |
C15—C17—H17C | 109.5 | C23D—C21D—H21D | 107.9 |
H17A—C17—H17C | 109.5 | C22D—C21D—H21D | 107.9 |
H17B—C17—H17C | 109.5 | C6—C21D—H21D | 107.9 |
C20—C18—C19 | 114.2 (11) | C7D—C22D—C21D | 110 (3) |
C20—C18—C4 | 109.8 (10) | C7D—C22D—H22D | 109.8 |
C19—C18—C4 | 114.8 (10) | C21D—C22D—H22D | 109.8 |
C20—C18—H18 | 105.7 | C7D—C22D—H22E | 109.8 |
C19—C18—H18 | 105.7 | C21D—C22D—H22E | 109.8 |
C4—C18—H18 | 105.7 | H22D—C22D—H22E | 108.2 |
C18—C19—H19A | 109.5 | C21D—C23D—H23E | 109.5 |
C18—C19—H19B | 109.5 | C21D—C23D—H23D | 109.5 |
H19A—C19—H19B | 109.5 | H23E—C23D—H23D | 109.5 |
C18—C19—H19C | 109.5 | C21D—C23D—H23F | 109.5 |
H19A—C19—H19C | 109.5 | H23E—C23D—H23F | 109.5 |
H19B—C19—H19C | 109.5 | H23D—C23D—H23F | 109.5 |
C31H39NO3 | Dx = 1.237 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.70932 Å |
Orthorhombic, P212121 | Cell parameters from 1825 reflections |
a = 5.9907 (12) Å | θ = 2.4–24.8° |
b = 13.301 (5) Å | µ = 0.08 mm−1 |
c = 31.928 (9) Å | T = 299 K |
V = 2544.1 (13) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.18 × 0.14 mm |
F(000) = 1024 |
Bruker APEX-II CCD diffractometer | Rint = 0.182 |
φ– and ω scans | θmax = 25.0°, θmin = 1.7° |
15004 measured reflections | h = −7→7 |
2311 independent reflections | k = −12→12 |
1039 reflections with I > 2σ(I) | l = −31→31 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.079 | w = 1/[σ2(Fo2) + (0.0919P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.203 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 0.14 e Å−3 |
2311 reflections | Δρmin = −0.15 e Å−3 |
259 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
225 restraints | Absolute structure parameter: −2.8 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O2 | 0.3828 (14) | 0.6251 (7) | 0.4829 (3) | 0.068 (3) | |
O3 | 0.6937 (16) | 0.6163 (7) | 0.4452 (3) | 0.076 (3) | |
C1 | 0.1806 (17) | 0.2604 (9) | 0.3102 (4) | 0.0502 (14)* | |
C2 | 0.0991 (17) | 0.3242 (10) | 0.2787 (4) | 0.0502 (14)* | |
C3 | 0.1630 (16) | 0.3079 (9) | 0.2375 (4) | 0.0502 (14)* | |
H3 | 0.1072 | 0.3498 | 0.2167 | 0.060* | |
C4 | 0.3045 (17) | 0.2325 (10) | 0.2266 (4) | 0.0502 (14)* | |
C5 | 0.3820 (16) | 0.1694 (10) | 0.2587 (4) | 0.0502 (14)* | |
H5 | 0.4749 | 0.1160 | 0.2517 | 0.060* | |
C6 | 0.3253 (18) | 0.1835 (9) | 0.3005 (4) | 0.0502 (14)* | |
C14 | 0.498 (2) | 0.5866 (11) | 0.4542 (4) | 0.052 (4) | |
C18 | 0.3671 (19) | 0.2074 (11) | 0.1819 (4) | 0.072 (4)* | |
H18 | 0.3572 | 0.1340 | 0.1799 | 0.087* | |
C19 | 0.6088 (19) | 0.2326 (12) | 0.1733 (4) | 0.086 (5)* | |
H19A | 0.7005 | 0.2056 | 0.1952 | 0.129* | |
H19B | 0.6527 | 0.2038 | 0.1470 | 0.129* | |
H19C | 0.6267 | 0.3042 | 0.1722 | 0.129* | |
C20 | 0.212 (2) | 0.2473 (11) | 0.1486 (5) | 0.097 (5)* | |
H20A | 0.0609 | 0.2295 | 0.1555 | 0.145* | |
H20B | 0.2248 | 0.3192 | 0.1472 | 0.145* | |
H20C | 0.2509 | 0.2187 | 0.1220 | 0.145* | |
C26 | 0.940 (2) | 0.5155 (11) | 0.5497 (4) | 0.059 (4)* | |
N1 | 0.9601 (15) | 0.6715 (7) | 0.5092 (3) | 0.057 (3) | |
H1A | 0.8506 | 0.6534 | 0.4920 | 0.068* | |
H1B | 1.0898 | 0.6490 | 0.4994 | 0.068* | |
H1C | 0.9646 | 0.7383 | 0.5111 | 0.068* | |
C24 | 0.6970 (18) | 0.6664 (10) | 0.5690 (4) | 0.077 (4)* | |
H24A | 0.6717 | 0.6379 | 0.5963 | 0.115* | |
H24B | 0.7019 | 0.7383 | 0.5712 | 0.115* | |
H24C | 0.5779 | 0.6470 | 0.5506 | 0.115* | |
C25 | 0.919 (2) | 0.6278 (12) | 0.5517 (4) | 0.066 (4)* | |
H25 | 1.0371 | 0.6524 | 0.5702 | 0.079* | |
C27 | 1.139 (2) | 0.4687 (11) | 0.5595 (4) | 0.070 (4)* | |
H27 | 1.2617 | 0.5070 | 0.5675 | 0.084* | |
C28 | 1.156 (2) | 0.3657 (12) | 0.5576 (5) | 0.085 (5)* | |
H28 | 1.2891 | 0.3354 | 0.5659 | 0.102* | |
C29 | 0.993 (2) | 0.3091 (13) | 0.5444 (5) | 0.090 (5)* | |
H29 | 1.0115 | 0.2398 | 0.5435 | 0.107* | |
C30 | 0.795 (2) | 0.3501 (12) | 0.5321 (5) | 0.088 (5)* | |
H30 | 0.6803 | 0.3095 | 0.5224 | 0.106* | |
C31 | 0.768 (2) | 0.4569 (11) | 0.5343 (4) | 0.070 (4)* | |
H31 | 0.6352 | 0.4866 | 0.5255 | 0.083* | |
O1 | −0.054 (3) | 0.2269 (12) | 0.3690 (5) | 0.074 (5) | 0.745 (4) |
C7 | 0.104 (3) | 0.2733 (14) | 0.3552 (5) | 0.061 (6)* | 0.745 (4) |
C8 | 0.2140 (19) | 0.3494 (9) | 0.3820 (4) | 0.041 (3)* | 0.745 (4) |
C9 | 0.105 (2) | 0.3856 (11) | 0.4161 (4) | 0.049 (4)* | 0.745 (4) |
H9 | −0.0342 | 0.3594 | 0.4233 | 0.058* | 0.745 (4) |
C10 | 0.198 (2) | 0.4604 (11) | 0.4400 (4) | 0.054 (4)* | 0.745 (4) |
H10 | 0.1241 | 0.4823 | 0.4640 | 0.065* | 0.745 (4) |
C11 | 0.398 (2) | 0.5035 (11) | 0.4290 (4) | 0.049 (4)* | 0.745 (4) |
C12 | 0.514 (2) | 0.4629 (11) | 0.3958 (4) | 0.053 (4)* | 0.745 (4) |
H12 | 0.6574 | 0.4854 | 0.3898 | 0.063* | 0.745 (4) |
C13 | 0.418 (2) | 0.3894 (11) | 0.3715 (4) | 0.052 (4)* | 0.745 (4) |
H13 | 0.4924 | 0.3664 | 0.3478 | 0.062* | 0.745 (4) |
C15 | −0.047 (2) | 0.4137 (11) | 0.2906 (4) | 0.056 (4) | 0.745 (4) |
H15 | −0.0710 | 0.4096 | 0.3209 | 0.067* | 0.745 (4) |
C16 | −0.2744 (19) | 0.4058 (11) | 0.2702 (4) | 0.057 (4) | 0.745 (4) |
H16A | −0.3389 | 0.3415 | 0.2766 | 0.085* | 0.745 (4) |
H16B | −0.3695 | 0.4582 | 0.2807 | 0.085* | 0.745 (4) |
H16C | −0.2592 | 0.4128 | 0.2404 | 0.085* | 0.745 (4) |
C17 | 0.068 (2) | 0.5109 (11) | 0.2827 (5) | 0.073 (5) | 0.745 (4) |
H17A | 0.2105 | 0.5109 | 0.2964 | 0.110* | 0.745 (4) |
H17B | 0.0888 | 0.5196 | 0.2531 | 0.110* | 0.745 (4) |
H17C | −0.0215 | 0.5650 | 0.2934 | 0.110* | 0.745 (4) |
C21 | 0.399 (3) | 0.1082 (12) | 0.3330 (5) | 0.056 (5) | 0.745 (4) |
H21 | 0.4259 | 0.1472 | 0.3586 | 0.067* | 0.745 (4) |
C22 | 0.220 (3) | 0.0320 (13) | 0.3443 (5) | 0.086 (6) | 0.745 (4) |
H22A | 0.2774 | −0.0136 | 0.3650 | 0.129* | 0.745 (4) |
H22B | 0.0922 | 0.0664 | 0.3554 | 0.129* | 0.745 (4) |
H22C | 0.1779 | −0.0050 | 0.3198 | 0.129* | 0.745 (4) |
C23 | 0.619 (2) | 0.0567 (14) | 0.3232 (5) | 0.075 (6) | 0.745 (4) |
H23A | 0.6541 | 0.0102 | 0.3452 | 0.113* | 0.745 (4) |
H23B | 0.6061 | 0.0211 | 0.2972 | 0.113* | 0.745 (4) |
H23C | 0.7348 | 0.1061 | 0.3211 | 0.113* | 0.745 (4) |
O1D | −0.124 (5) | 0.263 (4) | 0.3578 (17) | 0.057 (19)* | 0.176 (4) |
C7D | 0.117 (6) | 0.260 (2) | 0.3576 (8) | 0.07 (2)* | 0.176 (4) |
C8D | 0.2140 (19) | 0.3494 (9) | 0.3820 (4) | 0.041 (3)* | 0.176 (4) |
C9D | 0.105 (2) | 0.3856 (11) | 0.4161 (4) | 0.049 (4)* | 0.176 (4) |
H9D | −0.0342 | 0.3594 | 0.4233 | 0.058* | 0.176 (4) |
C10D | 0.198 (2) | 0.4604 (11) | 0.4400 (4) | 0.054 (4)* | 0.176 (4) |
H10D | 0.1241 | 0.4823 | 0.4640 | 0.065* | 0.176 (4) |
C11D | 0.398 (2) | 0.5035 (11) | 0.4290 (4) | 0.049 (4)* | 0.176 (4) |
C12D | 0.514 (2) | 0.4629 (11) | 0.3958 (4) | 0.053 (4)* | 0.176 (4) |
H12D | 0.6574 | 0.4854 | 0.3898 | 0.063* | 0.176 (4) |
C13D | 0.418 (2) | 0.3894 (11) | 0.3715 (4) | 0.052 (4)* | 0.176 (4) |
H13D | 0.4924 | 0.3664 | 0.3478 | 0.062* | 0.176 (4) |
C15D | −0.047 (2) | 0.4137 (11) | 0.2906 (4) | 0.056 (4) | 0.176 (4) |
H15D | −0.0710 | 0.4096 | 0.3209 | 0.067* | 0.176 (4) |
C16D | −0.2744 (19) | 0.4058 (11) | 0.2702 (4) | 0.057 (4) | 0.176 (4) |
H16D | −0.3389 | 0.3415 | 0.2766 | 0.085* | 0.176 (4) |
H16E | −0.3695 | 0.4582 | 0.2807 | 0.085* | 0.176 (4) |
H16F | −0.2592 | 0.4128 | 0.2404 | 0.085* | 0.176 (4) |
C17D | 0.068 (2) | 0.5109 (11) | 0.2827 (5) | 0.073 (5) | 0.176 (4) |
H17D | 0.2105 | 0.5109 | 0.2964 | 0.110* | 0.176 (4) |
H17E | 0.0888 | 0.5196 | 0.2531 | 0.110* | 0.176 (4) |
H17F | −0.0215 | 0.5650 | 0.2934 | 0.110* | 0.176 (4) |
C21D | 0.418 (9) | 0.135 (4) | 0.3402 (10) | 0.060 (11)* | 0.176 (4) |
H21D | 0.5520 | 0.1713 | 0.3491 | 0.073* | 0.176 (4) |
C22D | 0.225 (9) | 0.160 (3) | 0.3699 (14) | 0.078 (18)* | 0.176 (4) |
H22D | 0.1148 | 0.1069 | 0.3690 | 0.094* | 0.176 (4) |
H22E | 0.2812 | 0.1647 | 0.3984 | 0.094* | 0.176 (4) |
C23D | 0.478 (14) | 0.027 (4) | 0.333 (2) | 0.09 (2)* | 0.176 (4) |
H23D | 0.5353 | −0.0018 | 0.3582 | 0.130* | 0.176 (4) |
H23E | 0.3469 | −0.0094 | 0.3243 | 0.130* | 0.176 (4) |
H23F | 0.5888 | 0.0228 | 0.3112 | 0.130* | 0.176 (4) |
O1P | −0.082 (16) | 0.256 (7) | 0.371 (2) | 0.08 (3)* | 0.079 (4) |
C7P | 0.038 (7) | 0.314 (3) | 0.3428 (8) | 0.07 (2)* | 0.079 (4) |
C8P | 0.163 (9) | 0.391 (5) | 0.3699 (15) | 0.023 (18)* | 0.079 (4) |
C9P | 0.050 (9) | 0.425 (6) | 0.4051 (19) | 0.030 (18)* | 0.079 (4) |
H9P | −0.0965 | 0.4055 | 0.4104 | 0.036* | 0.079 (4) |
C10P | 0.162 (9) | 0.489 (5) | 0.4320 (18) | 0.038 (19)* | 0.079 (4) |
H10P | 0.0911 | 0.5126 | 0.4559 | 0.046* | 0.079 (4) |
C11P | 0.381 (7) | 0.517 (2) | 0.4237 (11) | 0.049 (19)* | 0.079 (4) |
C12P | 0.493 (10) | 0.483 (5) | 0.3884 (18) | 0.046 (19)* | 0.079 (4) |
H12P | 0.6390 | 0.5026 | 0.3831 | 0.055* | 0.079 (4) |
C13P | 0.381 (11) | 0.419 (6) | 0.361 (2) | 0.048 (19)* | 0.079 (4) |
H13P | 0.4512 | 0.3948 | 0.3369 | 0.058* | 0.079 (4) |
C15P | −0.076 (8) | 0.378 (5) | 0.3045 (12) | 0.058 (12)* | 0.079 (4) |
C16P | −0.318 (8) | 0.356 (11) | 0.295 (3) | 0.08 (2)* | 0.079 (4) |
H16G | −0.4107 | 0.3945 | 0.3135 | 0.117* | 0.079 (4) |
H16H | −0.3495 | 0.3739 | 0.2665 | 0.117* | 0.079 (4) |
H16I | −0.3466 | 0.2856 | 0.2991 | 0.117* | 0.079 (4) |
C17P | −0.03 (2) | 0.491 (4) | 0.305 (3) | 0.07 (2)* | 0.079 (4) |
H17G | 0.1267 | 0.5017 | 0.3114 | 0.107* | 0.079 (4) |
H17H | −0.0638 | 0.5193 | 0.2785 | 0.107* | 0.079 (4) |
H17I | −0.1182 | 0.5219 | 0.3265 | 0.107* | 0.079 (4) |
C21P | 0.399 (3) | 0.1082 (12) | 0.3330 (5) | 0.056 (5) | 0.079 (4) |
H21P | 0.4259 | 0.1472 | 0.3586 | 0.067* | 0.079 (4) |
C22P | 0.220 (3) | 0.0320 (13) | 0.3443 (5) | 0.086 (6) | 0.079 (4) |
H22F | 0.2774 | −0.0136 | 0.3650 | 0.129* | 0.079 (4) |
H22G | 0.0922 | 0.0664 | 0.3554 | 0.129* | 0.079 (4) |
H22H | 0.1779 | −0.0050 | 0.3198 | 0.129* | 0.079 (4) |
C23P | 0.619 (2) | 0.0567 (14) | 0.3232 (5) | 0.075 (6) | 0.079 (4) |
H23G | 0.6541 | 0.0102 | 0.3452 | 0.113* | 0.079 (4) |
H23H | 0.6061 | 0.0211 | 0.2972 | 0.113* | 0.079 (4) |
H23I | 0.7348 | 0.1061 | 0.3211 | 0.113* | 0.079 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.074 (6) | 0.056 (9) | 0.075 (9) | 0.007 (5) | 0.007 (5) | −0.028 (5) |
O3 | 0.072 (5) | 0.069 (9) | 0.086 (9) | −0.035 (6) | 0.005 (6) | −0.014 (5) |
C14 | 0.071 (9) | 0.029 (13) | 0.056 (13) | 0.011 (9) | −0.022 (9) | −0.004 (7) |
N1 | 0.060 (6) | 0.037 (10) | 0.073 (10) | −0.014 (6) | −0.006 (6) | 0.002 (5) |
O1 | 0.105 (10) | 0.059 (13) | 0.059 (11) | −0.017 (10) | 0.017 (9) | −0.024 (7) |
C15 | 0.072 (8) | 0.043 (11) | 0.053 (10) | 0.005 (8) | −0.001 (7) | 0.002 (6) |
C16 | 0.065 (8) | 0.041 (13) | 0.065 (12) | −0.005 (8) | 0.007 (8) | 0.006 (6) |
C17 | 0.056 (8) | 0.041 (14) | 0.123 (15) | 0.005 (8) | 0.014 (9) | −0.016 (8) |
C21 | 0.078 (10) | 0.052 (12) | 0.036 (10) | 0.020 (9) | −0.004 (8) | 0.003 (7) |
C22 | 0.109 (13) | 0.056 (15) | 0.093 (15) | −0.008 (12) | −0.009 (11) | 0.038 (9) |
C23 | 0.094 (12) | 0.078 (15) | 0.055 (14) | 0.027 (11) | −0.010 (10) | 0.009 (8) |
C15D | 0.072 (8) | 0.043 (11) | 0.053 (10) | 0.005 (8) | −0.001 (7) | 0.002 (6) |
C16D | 0.065 (8) | 0.041 (13) | 0.065 (12) | −0.005 (8) | 0.007 (8) | 0.006 (6) |
C17D | 0.056 (8) | 0.041 (14) | 0.123 (15) | 0.005 (8) | 0.014 (9) | −0.016 (8) |
C21P | 0.078 (10) | 0.052 (12) | 0.036 (10) | 0.020 (9) | −0.004 (8) | 0.003 (7) |
C22P | 0.109 (13) | 0.056 (15) | 0.093 (15) | −0.008 (12) | −0.009 (11) | 0.038 (9) |
C23P | 0.094 (12) | 0.078 (15) | 0.055 (14) | 0.027 (11) | −0.010 (10) | 0.009 (8) |
O2—C14 | 1.257 (14) | C8—C13 | 1.376 (15) |
O3—C14 | 1.268 (14) | C9—C10 | 1.372 (16) |
C1—C6 | 1.376 (14) | C10—C11 | 1.375 (15) |
C1—C2 | 1.401 (15) | C11—C12 | 1.379 (16) |
C1—C7 | 1.517 (16) | C12—C13 | 1.373 (17) |
C1—C7P | 1.53 (2) | C15—C17 | 1.485 (18) |
C1—C7D | 1.56 (2) | C15—C16 | 1.515 (16) |
C2—C3 | 1.389 (14) | C21—C23 | 1.515 (17) |
C2—C15P | 1.51 (2) | C21—C22 | 1.520 (17) |
C2—C15 | 1.525 (17) | O1D—C7D | 1.44 (3) |
C2—C15D | 1.525 (17) | C7D—C22D | 1.53 (3) |
C3—C4 | 1.358 (14) | C7D—C8D | 1.54 (2) |
C4—C5 | 1.404 (15) | C8D—C9D | 1.360 (14) |
C4—C18 | 1.513 (16) | C8D—C13D | 1.376 (15) |
C5—C6 | 1.392 (14) | C9D—C10D | 1.372 (16) |
C6—C21P | 1.508 (16) | C10D—C11D | 1.375 (15) |
C6—C21 | 1.508 (16) | C11D—C12D | 1.379 (16) |
C6—C21D | 1.53 (2) | C12D—C13D | 1.373 (17) |
C14—C11D | 1.493 (18) | C15D—C17D | 1.485 (18) |
C14—C11 | 1.493 (18) | C15D—C16D | 1.515 (16) |
C14—C11P | 1.52 (2) | C21D—C23D | 1.50 (3) |
C18—C20 | 1.509 (16) | C21D—C22D | 1.53 (3) |
C18—C19 | 1.511 (15) | O1P—C7P | 1.39 (3) |
C26—C27 | 1.381 (15) | C7P—C8P | 1.54 (2) |
C26—C31 | 1.382 (15) | C7P—C15P | 1.64 (3) |
C26—C25 | 1.501 (17) | C8P—C13P | 1.38 (3) |
N1—C25 | 1.495 (15) | C8P—C9P | 1.39 (3) |
C24—C25 | 1.529 (15) | C9P—C10P | 1.38 (3) |
C27—C28 | 1.375 (16) | C10P—C11P | 1.39 (3) |
C28—C29 | 1.304 (17) | C11P—C12P | 1.39 (3) |
C29—C30 | 1.361 (17) | C12P—C13P | 1.40 (3) |
C30—C31 | 1.432 (18) | C15P—C16P | 1.51 (3) |
O1—C7 | 1.214 (15) | C15P—C17P | 1.53 (3) |
C7—C8 | 1.480 (17) | C21P—C23P | 1.515 (17) |
C8—C9 | 1.360 (14) | C21P—C22P | 1.520 (17) |
C6—C1—C2 | 120.6 (11) | C12—C11—C14 | 120.1 (12) |
C6—C1—C7 | 119.1 (11) | C13—C12—C11 | 120.2 (12) |
C2—C1—C7 | 120.3 (12) | C12—C13—C8 | 120.6 (12) |
C6—C1—C7P | 148.6 (17) | C17—C15—C16 | 113.8 (12) |
C2—C1—C7P | 90.7 (15) | C17—C15—C2 | 111.9 (11) |
C6—C1—C7D | 111.5 (16) | C16—C15—C2 | 110.8 (11) |
C2—C1—C7D | 127.8 (17) | C6—C21—C23 | 114.5 (13) |
C3—C2—C1 | 119.2 (12) | C6—C21—C22 | 113.5 (11) |
C3—C2—C15P | 141.4 (18) | C23—C21—C22 | 111.0 (14) |
C1—C2—C15P | 97.8 (16) | O1D—C7D—C22D | 116 (3) |
C3—C2—C15 | 121.0 (10) | O1D—C7D—C8D | 111 (3) |
C1—C2—C15 | 119.6 (11) | C22D—C7D—C8D | 112 (3) |
C3—C2—C15D | 121.0 (10) | O1D—C7D—C1 | 104 (3) |
C1—C2—C15D | 119.6 (11) | C22D—C7D—C1 | 99 (2) |
C4—C3—C2 | 122.1 (12) | C8D—C7D—C1 | 113.3 (19) |
C3—C4—C5 | 117.4 (12) | C9D—C8D—C13D | 119.1 (11) |
C3—C4—C18 | 124.0 (11) | C9D—C8D—C7D | 119.9 (14) |
C5—C4—C18 | 118.3 (12) | C13D—C8D—C7D | 120.8 (15) |
C6—C5—C4 | 122.7 (12) | C8D—C9D—C10D | 120.4 (11) |
C1—C6—C5 | 118.0 (10) | C9D—C10D—C11D | 121.0 (13) |
C1—C6—C21P | 121.7 (12) | C10D—C11D—C12D | 118.2 (13) |
C5—C6—C21P | 119.9 (12) | C10D—C11D—C14 | 121.5 (14) |
C1—C6—C21 | 121.7 (12) | C12D—C11D—C14 | 120.1 (12) |
C5—C6—C21 | 119.9 (12) | C13D—C12D—C11D | 120.2 (12) |
C1—C6—C21D | 111.1 (17) | C12D—C13D—C8D | 120.6 (12) |
C5—C6—C21D | 130.5 (17) | C17D—C15D—C16D | 113.8 (12) |
O2—C14—O3 | 123.1 (12) | C17D—C15D—C2 | 111.9 (11) |
O2—C14—C11D | 118.2 (13) | C16D—C15D—C2 | 110.8 (11) |
O3—C14—C11D | 118.7 (13) | C23D—C21D—C6 | 111 (4) |
O2—C14—C11 | 118.2 (13) | C23D—C21D—C22D | 119 (4) |
O3—C14—C11 | 118.7 (13) | C6—C21D—C22D | 98 (2) |
O2—C14—C11P | 118 (2) | C7D—C22D—C21D | 111 (3) |
O3—C14—C11P | 118 (2) | O1P—C7P—C1 | 118 (4) |
C20—C18—C19 | 112.6 (12) | O1P—C7P—C8P | 105 (3) |
C20—C18—C4 | 115.7 (11) | C1—C7P—C8P | 115 (3) |
C19—C18—C4 | 111.1 (11) | O1P—C7P—C15P | 124 (4) |
C27—C26—C31 | 118.1 (14) | C1—C7P—C15P | 87.9 (15) |
C27—C26—C25 | 120.8 (13) | C8P—C7P—C15P | 106 (3) |
C31—C26—C25 | 120.8 (11) | C13P—C8P—C9P | 123 (3) |
N1—C25—C26 | 109.6 (10) | C13P—C8P—C7P | 121 (3) |
N1—C25—C24 | 110.0 (11) | C9P—C8P—C7P | 116 (3) |
C26—C25—C24 | 115.0 (11) | C10P—C9P—C8P | 118 (3) |
C28—C27—C26 | 120.3 (14) | C9P—C10P—C11P | 121 (3) |
C29—C28—C27 | 122.1 (15) | C12P—C11P—C10P | 121 (3) |
C28—C29—C30 | 121.0 (17) | C12P—C11P—C14 | 120 (3) |
C29—C30—C31 | 119.0 (15) | C10P—C11P—C14 | 119 (3) |
C26—C31—C30 | 119.3 (13) | C11P—C12P—C13P | 119 (3) |
O1—C7—C8 | 118.9 (15) | C8P—C13P—C12P | 119 (3) |
O1—C7—C1 | 121.5 (14) | C16P—C15P—C2 | 118 (4) |
C8—C7—C1 | 119.4 (13) | C16P—C15P—C17P | 112 (3) |
C9—C8—C13 | 119.1 (11) | C2—C15P—C17P | 110 (4) |
C9—C8—C7 | 119.4 (11) | C16P—C15P—C7P | 117 (4) |
C13—C8—C7 | 121.3 (13) | C2—C15P—C7P | 82.9 (15) |
C8—C9—C10 | 120.4 (11) | C17P—C15P—C7P | 115 (4) |
C9—C10—C11 | 121.0 (13) | C6—C21P—C23P | 114.5 (13) |
C10—C11—C12 | 118.2 (13) | C6—C21P—C22P | 113.5 (11) |
C10—C11—C14 | 121.5 (14) | C23P—C21P—C22P | 111.0 (14) |
C31H39NO3 | Dx = 1.112 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 6751 reflections |
a = 6.2884 (3) Å | θ = 1.9–23.1° |
b = 13.7572 (5) Å | µ = 0.07 mm−1 |
c = 32.7030 (13) Å | T = 299 K |
V = 2829.2 (2) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.18 × 0.14 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 5496 independent reflections |
Radiation source: fine-focus sealed tube | 4027 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −7→6 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −16→16 |
Tmin = 0.995, Tmax = 1.000 | l = −38→39 |
25524 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + (0.0463P)2 + 0.3002P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.114 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.11 e Å−3 |
5496 reflections | Δρmin = −0.13 e Å−3 |
505 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
560 restraints | Absolute structure parameter: 2.0 (6) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 1.0340 (11) | 0.2438 (4) | 0.63069 (18) | 0.0815 (18) | 0.740 (4) |
O2 | 0.6228 (3) | 0.63113 (15) | 0.51713 (7) | 0.0599 (6) | 0.740 (4) |
O3 | 0.3222 (4) | 0.61925 (18) | 0.55187 (7) | 0.0703 (7) | 0.740 (4) |
C1 | 0.8160 (18) | 0.2758 (7) | 0.6882 (2) | 0.043 (2) | 0.740 (4) |
C2 | 0.886 (2) | 0.3407 (9) | 0.7181 (3) | 0.049 (3) | 0.740 (4) |
C3 | 0.826 (3) | 0.3252 (12) | 0.7589 (4) | 0.053 (3) | 0.740 (4) |
H3 | 0.8760 | 0.3676 | 0.7788 | 0.064* | 0.740 (4) |
C4 | 0.696 (3) | 0.2500 (12) | 0.7704 (3) | 0.054 (3) | 0.740 (4) |
C5 | 0.624 (3) | 0.1886 (11) | 0.7396 (3) | 0.053 (3) | 0.740 (4) |
H5 | 0.5316 | 0.1387 | 0.7466 | 0.064* | 0.740 (4) |
C6 | 0.684 (3) | 0.1976 (9) | 0.6984 (3) | 0.048 (3) | 0.740 (4) |
C7 | 0.8893 (13) | 0.2920 (5) | 0.6447 (2) | 0.0490 (18) | 0.740 (4) |
C8 | 0.7790 (12) | 0.3667 (5) | 0.6195 (2) | 0.042 (2) | 0.740 (4) |
C9 | 0.8710 (12) | 0.3944 (6) | 0.5826 (2) | 0.053 (2) | 0.740 (4) |
H9 | 0.9944 | 0.3631 | 0.5741 | 0.064* | 0.740 (4) |
C10 | 0.7867 (13) | 0.4661 (5) | 0.5582 (3) | 0.0510 (19) | 0.740 (4) |
H10 | 0.8548 | 0.4842 | 0.5342 | 0.061* | 0.740 (4) |
C11 | 0.6017 (14) | 0.5105 (6) | 0.5698 (3) | 0.042 (3) | 0.740 (4) |
C12 | 0.4974 (13) | 0.4797 (6) | 0.6050 (2) | 0.052 (2) | 0.740 (4) |
H12 | 0.3671 | 0.5067 | 0.6122 | 0.063* | 0.740 (4) |
C13 | 0.5885 (9) | 0.4085 (5) | 0.62934 (19) | 0.0476 (17) | 0.740 (4) |
H13 | 0.5185 | 0.3887 | 0.6530 | 0.057* | 0.740 (4) |
C14 | 0.5081 (5) | 0.5932 (2) | 0.54472 (9) | 0.0488 (7) | 0.740 (4) |
C15 | 1.0251 (19) | 0.4284 (8) | 0.7076 (5) | 0.060 (3) | 0.740 (4) |
H15 | 1.0372 | 0.4318 | 0.6778 | 0.072* | 0.740 (4) |
C16 | 1.2494 (15) | 0.4172 (8) | 0.7252 (3) | 0.066 (2) | 0.740 (4) |
H16A | 1.3329 | 0.4731 | 0.7181 | 0.099* | 0.740 (4) |
H16B | 1.2415 | 0.4114 | 0.7544 | 0.099* | 0.740 (4) |
H16C | 1.3146 | 0.3599 | 0.7140 | 0.099* | 0.740 (4) |
C17 | 0.9222 (17) | 0.5240 (6) | 0.7226 (4) | 0.086 (3) | 0.740 (4) |
H17A | 1.0125 | 0.5778 | 0.7156 | 0.129* | 0.740 (4) |
H17B | 0.7861 | 0.5322 | 0.7098 | 0.129* | 0.740 (4) |
H17C | 0.9042 | 0.5215 | 0.7517 | 0.129* | 0.740 (4) |
C18 | 0.6363 (17) | 0.2290 (10) | 0.8147 (3) | 0.069 (2) | 0.740 (4) |
H18 | 0.6471 | 0.1581 | 0.8168 | 0.083* | 0.740 (4) |
C19 | 0.7875 (13) | 0.2648 (10) | 0.8466 (2) | 0.092 (3) | 0.740 (4) |
H19A | 0.9305 | 0.2493 | 0.8387 | 0.137* | 0.740 (4) |
H19B | 0.7733 | 0.3340 | 0.8494 | 0.137* | 0.740 (4) |
H19C | 0.7556 | 0.2343 | 0.8723 | 0.137* | 0.740 (4) |
C20 | 0.4076 (10) | 0.2489 (8) | 0.8235 (2) | 0.085 (2) | 0.740 (4) |
H20A | 0.3216 | 0.2238 | 0.8017 | 0.128* | 0.740 (4) |
H20B | 0.3682 | 0.2180 | 0.8487 | 0.128* | 0.740 (4) |
H20C | 0.3859 | 0.3178 | 0.8258 | 0.128* | 0.740 (4) |
C21 | 0.6113 (17) | 0.1268 (7) | 0.6657 (2) | 0.065 (3) | 0.740 (4) |
H21 | 0.5914 | 0.1643 | 0.6405 | 0.078* | 0.740 (4) |
C22 | 0.7803 (13) | 0.0504 (5) | 0.6569 (2) | 0.083 (2) | 0.740 (4) |
H22A | 0.7299 | 0.0068 | 0.6362 | 0.124* | 0.740 (4) |
H22B | 0.9079 | 0.0817 | 0.6477 | 0.124* | 0.740 (4) |
H22C | 0.8098 | 0.0145 | 0.6815 | 0.124* | 0.740 (4) |
C23 | 0.3986 (11) | 0.0784 (5) | 0.6755 (2) | 0.077 (2) | 0.740 (4) |
H23A | 0.3610 | 0.0347 | 0.6538 | 0.115* | 0.740 (4) |
H23B | 0.4107 | 0.0429 | 0.7006 | 0.115* | 0.740 (4) |
H23C | 0.2906 | 0.1273 | 0.6782 | 0.115* | 0.740 (4) |
O1D | 1.088 (4) | 0.2710 (19) | 0.6371 (9) | 0.055 (6)* | 0.184 (4) |
O2D | 0.6228 (3) | 0.63113 (15) | 0.51713 (7) | 0.0599 (6) | 0.184 (4) |
O3D | 0.3222 (4) | 0.61925 (18) | 0.55187 (7) | 0.0703 (7) | 0.184 (4) |
C1D | 0.810 (8) | 0.286 (3) | 0.6888 (9) | 0.049 (11)* | 0.184 (4) |
C2D | 0.892 (10) | 0.346 (4) | 0.7188 (12) | 0.047 (11)* | 0.184 (4) |
C3D | 0.843 (10) | 0.323 (4) | 0.7599 (13) | 0.047 (11)* | 0.184 (4) |
H3D | 0.8933 | 0.3640 | 0.7805 | 0.056* | 0.184 (4) |
C4D | 0.720 (8) | 0.241 (4) | 0.7708 (10) | 0.032 (8)* | 0.184 (4) |
C5D | 0.647 (11) | 0.181 (4) | 0.7398 (10) | 0.043 (9)* | 0.184 (4) |
H5D | 0.5794 | 0.1224 | 0.7460 | 0.052* | 0.184 (4) |
C6D | 0.677 (11) | 0.208 (4) | 0.6995 (10) | 0.051 (11)* | 0.184 (4) |
C7D | 0.862 (5) | 0.277 (2) | 0.6423 (9) | 0.063 (10)* | 0.184 (4) |
C8D | 0.787 (4) | 0.3581 (19) | 0.6138 (9) | 0.034 (8)* | 0.184 (4) |
C9D | 0.919 (4) | 0.4048 (18) | 0.5854 (8) | 0.026 (6)* | 0.184 (4) |
H9D | 1.0601 | 0.3866 | 0.5813 | 0.031* | 0.184 (4) |
C10D | 0.822 (4) | 0.482 (2) | 0.5637 (10) | 0.032 (7)* | 0.184 (4) |
H10D | 0.9051 | 0.5142 | 0.5446 | 0.039* | 0.184 (4) |
C11D | 0.610 (5) | 0.513 (2) | 0.5684 (10) | 0.043 (11)* | 0.184 (4) |
C12D | 0.491 (5) | 0.4623 (19) | 0.5972 (8) | 0.046 (9)* | 0.184 (4) |
H12D | 0.3503 | 0.4797 | 0.6017 | 0.055* | 0.184 (4) |
C13D | 0.579 (4) | 0.3865 (18) | 0.6194 (8) | 0.048 (8)* | 0.184 (4) |
H13D | 0.4952 | 0.3540 | 0.6385 | 0.058* | 0.184 (4) |
C14D | 0.5081 (5) | 0.5932 (2) | 0.54472 (9) | 0.0488 (7) | 0.184 (4) |
C15D | 1.047 (7) | 0.427 (3) | 0.7099 (17) | 0.049 (10)* | 0.184 (4) |
H15D | 1.0955 | 0.4155 | 0.6819 | 0.059* | 0.184 (4) |
C16D | 1.243 (7) | 0.421 (4) | 0.7359 (13) | 0.063 (9)* | 0.184 (4) |
H16D | 1.3357 | 0.4743 | 0.7290 | 0.094* | 0.184 (4) |
H16E | 1.2038 | 0.4258 | 0.7642 | 0.094* | 0.184 (4) |
H16F | 1.3144 | 0.3609 | 0.7310 | 0.094* | 0.184 (4) |
C17D | 0.937 (9) | 0.527 (3) | 0.7094 (17) | 0.080 (13)* | 0.184 (4) |
H17D | 0.8134 | 0.5240 | 0.6922 | 0.120* | 0.184 (4) |
H17E | 0.8951 | 0.5441 | 0.7367 | 0.120* | 0.184 (4) |
H17F | 1.0338 | 0.5747 | 0.6990 | 0.120* | 0.184 (4) |
C18D | 0.644 (6) | 0.214 (3) | 0.8152 (11) | 0.055 (6)* | 0.184 (4) |
H18D | 0.5911 | 0.1469 | 0.8155 | 0.066* | 0.184 (4) |
C19D | 0.825 (6) | 0.224 (3) | 0.8457 (11) | 0.097 (11)* | 0.184 (4) |
H19D | 0.9382 | 0.1809 | 0.8384 | 0.145* | 0.184 (4) |
H19E | 0.8760 | 0.2899 | 0.8455 | 0.145* | 0.184 (4) |
H19F | 0.7741 | 0.2084 | 0.8726 | 0.145* | 0.184 (4) |
C20D | 0.465 (5) | 0.284 (3) | 0.8277 (11) | 0.104 (10)* | 0.184 (4) |
H20D | 0.3493 | 0.2787 | 0.8087 | 0.157* | 0.184 (4) |
H20E | 0.4161 | 0.2681 | 0.8547 | 0.157* | 0.184 (4) |
H20F | 0.5180 | 0.3496 | 0.8275 | 0.157* | 0.184 (4) |
C21D | 0.602 (6) | 0.148 (2) | 0.6624 (9) | 0.068 (10)* | 0.184 (4) |
H21D | 0.4717 | 0.1790 | 0.6526 | 0.082* | 0.184 (4) |
C22D | 0.777 (3) | 0.1761 (14) | 0.6325 (6) | 0.080 (6)* | 0.184 (4) |
H22D | 0.7205 | 0.1753 | 0.6049 | 0.096* | 0.184 (4) |
H22E | 0.8914 | 0.1292 | 0.6340 | 0.096* | 0.184 (4) |
C23D | 0.547 (7) | 0.0450 (19) | 0.6712 (9) | 0.109 (10)* | 0.184 (4) |
H23D | 0.4332 | 0.0428 | 0.6908 | 0.164* | 0.184 (4) |
H23E | 0.5021 | 0.0137 | 0.6463 | 0.164* | 0.184 (4) |
H23F | 0.6689 | 0.0120 | 0.6820 | 0.164* | 0.184 (4) |
O1P | 1.113 (5) | 0.299 (2) | 0.6508 (11) | 0.063 (9)* | 0.076 (3) |
O2P | 0.6228 (3) | 0.63113 (15) | 0.51713 (7) | 0.0599 (6) | 0.076 (3) |
O3P | 0.3222 (4) | 0.61925 (18) | 0.55187 (7) | 0.0703 (7) | 0.076 (3) |
C1P | 0.779 (8) | 0.284 (3) | 0.6949 (11) | 0.044 (12)* | 0.076 (3) |
C2P | 0.835 (7) | 0.342 (3) | 0.7280 (12) | 0.039 (11)* | 0.076 (3) |
C3P | 0.765 (8) | 0.314 (4) | 0.7661 (12) | 0.055 (12)* | 0.076 (3) |
H3P | 0.7958 | 0.3528 | 0.7885 | 0.066* | 0.076 (3) |
C4P | 0.651 (8) | 0.230 (4) | 0.7724 (12) | 0.025 (10)* | 0.076 (3) |
C5P | 0.581 (11) | 0.174 (4) | 0.7397 (13) | 0.033 (11)* | 0.076 (3) |
H5P | 0.4895 | 0.1215 | 0.7433 | 0.040* | 0.076 (3) |
C6P | 0.655 (13) | 0.201 (4) | 0.7010 (14) | 0.044 (13)* | 0.076 (3) |
C7P | 0.925 (4) | 0.339 (2) | 0.6666 (8) | 0.063 (10)* | 0.076 (3) |
C8P | 0.814 (5) | 0.4040 (17) | 0.6350 (8) | 0.047 (9)* | 0.076 (3) |
C9P | 0.919 (5) | 0.442 (2) | 0.6020 (9) | 0.052 (9)* | 0.076 (3) |
H9P | 1.0618 | 0.4278 | 0.5983 | 0.062* | 0.076 (3) |
C10P | 0.818 (5) | 0.5020 (19) | 0.5737 (10) | 0.050 (10)* | 0.076 (3) |
H10P | 0.8956 | 0.5258 | 0.5518 | 0.060* | 0.076 (3) |
C11P | 0.607 (6) | 0.5273 (11) | 0.5770 (8) | 0.048 (12)* | 0.076 (3) |
C12P | 0.499 (7) | 0.490 (3) | 0.6104 (11) | 0.051 (13)* | 0.076 (3) |
H12P | 0.3555 | 0.5045 | 0.6139 | 0.062* | 0.076 (3) |
C13P | 0.600 (5) | 0.429 (3) | 0.6389 (12) | 0.050 (12)* | 0.076 (3) |
H13P | 0.5230 | 0.4057 | 0.6610 | 0.060* | 0.076 (3) |
C14P | 0.5081 (5) | 0.5932 (2) | 0.54472 (9) | 0.0488 (7) | 0.076 (3) |
C15P | 0.983 (7) | 0.409 (3) | 0.7069 (11) | 0.054 (12)* | 0.076 (3) |
C16P | 1.220 (7) | 0.401 (6) | 0.715 (2) | 0.078 (13)* | 0.076 (3) |
H16G | 1.2941 | 0.4488 | 0.6989 | 0.116* | 0.076 (3) |
H16H | 1.2479 | 0.4115 | 0.7433 | 0.116* | 0.076 (3) |
H16I | 1.2685 | 0.3372 | 0.7072 | 0.116* | 0.076 (3) |
C17P | 0.923 (15) | 0.515 (3) | 0.701 (3) | 0.10 (2)* | 0.076 (3) |
H17G | 1.0350 | 0.5483 | 0.6867 | 0.150* | 0.076 (3) |
H17H | 0.7941 | 0.5193 | 0.6851 | 0.150* | 0.076 (3) |
H17I | 0.9005 | 0.5452 | 0.7270 | 0.150* | 0.076 (3) |
C18P | 0.563 (8) | 0.207 (4) | 0.8150 (12) | 0.060 (7)* | 0.076 (3) |
H18P | 0.5514 | 0.1364 | 0.8187 | 0.072* | 0.076 (3) |
C19P | 0.717 (11) | 0.249 (8) | 0.846 (2) | 0.100 (14)* | 0.076 (3) |
H19G | 0.8515 | 0.2162 | 0.8445 | 0.149* | 0.076 (3) |
H19H | 0.7376 | 0.3172 | 0.8411 | 0.149* | 0.076 (3) |
H19I | 0.6600 | 0.2408 | 0.8734 | 0.149* | 0.076 (3) |
C20P | 0.345 (9) | 0.253 (8) | 0.815 (2) | 0.086 (13)* | 0.076 (3) |
H20G | 0.2586 | 0.2218 | 0.7942 | 0.129* | 0.076 (3) |
H20H | 0.2794 | 0.2443 | 0.8410 | 0.129* | 0.076 (3) |
H20I | 0.3570 | 0.3207 | 0.8087 | 0.129* | 0.076 (3) |
C21P | 0.583 (12) | 0.136 (5) | 0.6664 (18) | 0.063 (13)* | 0.076 (3) |
H21P | 0.6059 | 0.1680 | 0.6401 | 0.076* | 0.076 (3) |
C22P | 0.712 (13) | 0.041 (5) | 0.668 (3) | 0.09 (2)* | 0.076 (3) |
H22F | 0.6680 | −0.0011 | 0.6463 | 0.133* | 0.076 (3) |
H22G | 0.8607 | 0.0557 | 0.6652 | 0.133* | 0.076 (3) |
H22H | 0.6884 | 0.0096 | 0.6939 | 0.133* | 0.076 (3) |
C23P | 0.349 (11) | 0.107 (7) | 0.671 (3) | 0.12 (3)* | 0.076 (3) |
H23G | 0.3083 | 0.0655 | 0.6488 | 0.173* | 0.076 (3) |
H23H | 0.3292 | 0.0732 | 0.6964 | 0.173* | 0.076 (3) |
H23I | 0.2624 | 0.1645 | 0.6708 | 0.173* | 0.076 (3) |
N1 | 0.0382 (4) | 0.66931 (17) | 0.49138 (7) | 0.0480 (6) | |
H1A | 0.1377 | 0.6473 | 0.5084 | 0.058* | |
H1B | −0.0897 | 0.6532 | 0.5009 | 0.058* | |
H1C | 0.0478 | 0.7337 | 0.4895 | 0.058* | |
C24 | 0.2811 (6) | 0.6596 (3) | 0.43250 (11) | 0.0765 (11) | |
H24A | 0.3946 | 0.6395 | 0.4502 | 0.115* | |
H24B | 0.2801 | 0.7292 | 0.4305 | 0.115* | |
H24C | 0.3019 | 0.6320 | 0.4058 | 0.115* | |
C25 | 0.0699 (5) | 0.6249 (2) | 0.44984 (9) | 0.0573 (9) | |
H25 | −0.0428 | 0.6498 | 0.4320 | 0.069* | |
C26 | 0.0442 (6) | 0.5159 (3) | 0.45217 (9) | 0.0592 (9) | |
C27 | −0.1422 (7) | 0.4721 (3) | 0.43977 (11) | 0.0784 (11) | |
H27 | −0.2541 | 0.5104 | 0.4305 | 0.094* | |
C28 | −0.1653 (10) | 0.3718 (4) | 0.44096 (15) | 0.1092 (18) | |
H28 | −0.2922 | 0.3436 | 0.4325 | 0.131* | |
C29 | −0.0032 (14) | 0.3147 (4) | 0.45440 (17) | 0.120 (2) | |
H29 | −0.0182 | 0.2474 | 0.4546 | 0.144* | |
C30 | 0.1810 (12) | 0.3563 (4) | 0.46759 (15) | 0.1155 (17) | |
H30 | 0.2902 | 0.3172 | 0.4775 | 0.139* | |
C31 | 0.2073 (7) | 0.4567 (3) | 0.46639 (12) | 0.0825 (12) | |
H31 | 0.3344 | 0.4843 | 0.4751 | 0.099* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.100 (4) | 0.074 (4) | 0.071 (3) | 0.043 (4) | 0.030 (3) | 0.023 (3) |
O2 | 0.0587 (13) | 0.0590 (13) | 0.0620 (14) | 0.0031 (12) | 0.0025 (11) | 0.0263 (11) |
O3 | 0.0548 (14) | 0.0958 (18) | 0.0603 (14) | 0.0213 (13) | 0.0022 (11) | 0.0255 (13) |
C1 | 0.049 (4) | 0.036 (3) | 0.044 (4) | 0.016 (3) | 0.003 (2) | 0.011 (2) |
C2 | 0.050 (4) | 0.043 (4) | 0.055 (4) | 0.005 (3) | 0.010 (3) | 0.013 (2) |
C3 | 0.053 (5) | 0.055 (4) | 0.052 (4) | 0.002 (3) | −0.003 (3) | −0.008 (2) |
C4 | 0.048 (6) | 0.060 (6) | 0.053 (4) | 0.002 (5) | 0.006 (3) | 0.008 (3) |
C5 | 0.051 (6) | 0.051 (5) | 0.057 (4) | −0.006 (4) | −0.002 (3) | 0.016 (2) |
C6 | 0.059 (4) | 0.043 (4) | 0.041 (4) | 0.007 (3) | −0.005 (2) | 0.011 (2) |
C7 | 0.060 (4) | 0.043 (3) | 0.043 (3) | 0.009 (3) | 0.004 (2) | 0.007 (2) |
C8 | 0.058 (4) | 0.040 (3) | 0.026 (3) | 0.005 (2) | 0.004 (2) | 0.000 (2) |
C9 | 0.042 (4) | 0.059 (4) | 0.059 (4) | 0.009 (3) | 0.007 (3) | 0.009 (3) |
C10 | 0.057 (4) | 0.051 (4) | 0.045 (4) | −0.003 (3) | 0.006 (3) | 0.011 (3) |
C11 | 0.047 (4) | 0.043 (4) | 0.036 (3) | −0.002 (2) | −0.005 (2) | 0.0076 (18) |
C12 | 0.049 (4) | 0.067 (4) | 0.041 (4) | 0.012 (3) | 0.009 (3) | 0.012 (4) |
C13 | 0.062 (4) | 0.055 (4) | 0.026 (3) | 0.008 (3) | 0.011 (2) | 0.006 (3) |
C14 | 0.0512 (19) | 0.0512 (18) | 0.0440 (18) | −0.0017 (16) | −0.0051 (15) | 0.0074 (14) |
C15 | 0.062 (5) | 0.053 (4) | 0.065 (5) | −0.011 (3) | −0.003 (3) | 0.004 (2) |
C16 | 0.066 (4) | 0.076 (5) | 0.056 (7) | −0.010 (3) | 0.008 (4) | −0.010 (4) |
C17 | 0.067 (4) | 0.041 (3) | 0.151 (10) | −0.004 (3) | 0.016 (6) | 0.014 (5) |
C18 | 0.068 (4) | 0.089 (6) | 0.051 (3) | 0.006 (4) | 0.011 (3) | 0.003 (3) |
C19 | 0.087 (6) | 0.146 (9) | 0.042 (3) | 0.007 (6) | 0.003 (3) | 0.000 (4) |
C20 | 0.069 (5) | 0.116 (6) | 0.070 (5) | −0.011 (5) | 0.024 (4) | −0.010 (4) |
C21 | 0.095 (5) | 0.058 (4) | 0.043 (3) | −0.015 (4) | −0.018 (3) | 0.013 (3) |
C22 | 0.120 (6) | 0.067 (4) | 0.062 (4) | 0.013 (4) | 0.004 (4) | −0.023 (3) |
C23 | 0.082 (5) | 0.075 (4) | 0.074 (4) | −0.022 (4) | −0.021 (3) | 0.007 (3) |
O2D | 0.0587 (13) | 0.0590 (13) | 0.0620 (14) | 0.0031 (12) | 0.0025 (11) | 0.0263 (11) |
O3D | 0.0548 (14) | 0.0958 (18) | 0.0603 (14) | 0.0213 (13) | 0.0022 (11) | 0.0255 (13) |
C14D | 0.0512 (19) | 0.0512 (18) | 0.0440 (18) | −0.0017 (16) | −0.0051 (15) | 0.0074 (14) |
O2P | 0.0587 (13) | 0.0590 (13) | 0.0620 (14) | 0.0031 (12) | 0.0025 (11) | 0.0263 (11) |
O3P | 0.0548 (14) | 0.0958 (18) | 0.0603 (14) | 0.0213 (13) | 0.0022 (11) | 0.0255 (13) |
C14P | 0.0512 (19) | 0.0512 (18) | 0.0440 (18) | −0.0017 (16) | −0.0051 (15) | 0.0074 (14) |
N1 | 0.0450 (14) | 0.0505 (14) | 0.0486 (16) | 0.0030 (12) | −0.0007 (12) | 0.0113 (12) |
C24 | 0.091 (3) | 0.084 (3) | 0.054 (2) | −0.007 (2) | 0.022 (2) | 0.0034 (19) |
C25 | 0.063 (2) | 0.067 (2) | 0.0412 (19) | −0.0001 (18) | −0.0079 (15) | 0.0087 (15) |
C26 | 0.069 (2) | 0.068 (2) | 0.0410 (18) | −0.004 (2) | 0.0005 (16) | −0.0031 (16) |
C27 | 0.078 (3) | 0.093 (3) | 0.064 (2) | −0.015 (2) | 0.006 (2) | −0.013 (2) |
C28 | 0.121 (4) | 0.104 (4) | 0.103 (4) | −0.049 (4) | 0.031 (3) | −0.040 (3) |
C29 | 0.183 (7) | 0.071 (3) | 0.106 (4) | −0.019 (4) | 0.038 (4) | −0.013 (3) |
C30 | 0.160 (5) | 0.072 (3) | 0.115 (4) | 0.021 (4) | 0.004 (4) | 0.000 (3) |
C31 | 0.098 (3) | 0.067 (3) | 0.083 (3) | 0.001 (2) | −0.008 (2) | −0.002 (2) |
O1—C7 | 1.214 (7) | C18D—C20D | 1.54 (3) |
O2—C14 | 1.267 (3) | C18D—H18D | 0.9800 |
O3—C14 | 1.245 (4) | C19D—H19D | 0.9600 |
C1—C2 | 1.397 (8) | C19D—H19E | 0.9600 |
C1—C6 | 1.399 (8) | C19D—H19F | 0.9600 |
C1—C7 | 1.512 (8) | C20D—H20D | 0.9600 |
C2—C3 | 1.402 (9) | C20D—H20E | 0.9600 |
C2—C15 | 1.527 (9) | C20D—H20F | 0.9600 |
C3—C4 | 1.371 (9) | C21D—C23D | 1.49 (2) |
C3—H3 | 0.9300 | C21D—C22D | 1.52 (2) |
C4—C5 | 1.391 (9) | C21D—H21D | 0.9800 |
C4—C18 | 1.525 (9) | C22D—H22D | 0.9700 |
C5—C6 | 1.403 (9) | C22D—H22E | 0.9700 |
C5—H5 | 0.9300 | C23D—H23D | 0.9600 |
C6—C21 | 1.518 (8) | C23D—H23E | 0.9600 |
C7—C8 | 1.489 (7) | C23D—H23F | 0.9600 |
C8—C13 | 1.367 (8) | O1P—C7P | 1.40 (2) |
C8—C9 | 1.391 (8) | O2P—C14P | 1.267 (3) |
C9—C10 | 1.374 (7) | O3P—C14P | 1.245 (4) |
C9—H9 | 0.9300 | C1P—C6P | 1.39 (2) |
C10—C11 | 1.368 (8) | C1P—C2P | 1.40 (3) |
C10—H10 | 0.9300 | C1P—C7P | 1.51 (2) |
C11—C12 | 1.391 (8) | C2P—C3P | 1.38 (2) |
C11—C14 | 1.521 (7) | C2P—C15P | 1.48 (2) |
C12—C13 | 1.386 (7) | C3P—C4P | 1.37 (2) |
C12—H12 | 0.9300 | C3P—H3P | 0.9300 |
C13—H13 | 0.9300 | C4P—C5P | 1.39 (3) |
C15—C16 | 1.531 (10) | C4P—C18P | 1.53 (2) |
C15—C17 | 1.546 (11) | C5P—C6P | 1.40 (3) |
C15—H15 | 0.9800 | C5P—H5P | 0.9300 |
C16—H16A | 0.9600 | C6P—C21P | 1.52 (3) |
C16—H16B | 0.9600 | C7P—C8P | 1.54 (2) |
C16—H16C | 0.9600 | C7P—C15P | 1.67 (2) |
C17—H17A | 0.9600 | C8P—C9P | 1.37 (2) |
C17—H17B | 0.9600 | C8P—C13P | 1.39 (2) |
C17—H17C | 0.9600 | C9P—C10P | 1.39 (2) |
C18—C20 | 1.492 (10) | C9P—H9P | 0.9300 |
C18—C19 | 1.496 (10) | C10P—C11P | 1.38 (2) |
C18—H18 | 0.9800 | C10P—H10P | 0.9300 |
C19—H19A | 0.9600 | C11P—C12P | 1.39 (3) |
C19—H19B | 0.9600 | C11P—C14P | 1.52 (2) |
C19—H19C | 0.9600 | C12P—C13P | 1.40 (3) |
C20—H20A | 0.9600 | C12P—H12P | 0.9300 |
C20—H20B | 0.9600 | C13P—H13P | 0.9300 |
C20—H20C | 0.9600 | C15P—C16P | 1.52 (3) |
C21—C22 | 1.522 (11) | C15P—C17P | 1.52 (3) |
C21—C23 | 1.528 (10) | C16P—H16G | 0.9600 |
C21—H21 | 0.9800 | C16P—H16H | 0.9600 |
C22—H22A | 0.9600 | C16P—H16I | 0.9600 |
C22—H22B | 0.9600 | C17P—H17G | 0.9600 |
C22—H22C | 0.9600 | C17P—H17H | 0.9600 |
C23—H23A | 0.9600 | C17P—H17I | 0.9600 |
C23—H23B | 0.9600 | C18P—C20P | 1.51 (3) |
C23—H23C | 0.9600 | C18P—C19P | 1.53 (3) |
O1D—C7D | 1.44 (2) | C18P—H18P | 0.9800 |
O2D—C14D | 1.267 (3) | C19P—H19G | 0.9600 |
O3D—C14D | 1.245 (4) | C19P—H19H | 0.9600 |
C1D—C2D | 1.38 (2) | C19P—H19I | 0.9600 |
C1D—C6D | 1.40 (2) | C20P—H20G | 0.9600 |
C1D—C7D | 1.56 (2) | C20P—H20H | 0.9600 |
C2D—C3D | 1.41 (2) | C20P—H20I | 0.9600 |
C2D—C15D | 1.51 (2) | C21P—C22P | 1.53 (3) |
C3D—C4D | 1.42 (2) | C21P—C23P | 1.53 (3) |
C3D—H3D | 0.9300 | C21P—H21P | 0.9800 |
C4D—C5D | 1.39 (2) | C22P—H22F | 0.9600 |
C4D—C18D | 1.57 (2) | C22P—H22G | 0.9600 |
C5D—C6D | 1.38 (2) | C22P—H22H | 0.9600 |
C5D—H5D | 0.9300 | C23P—H23G | 0.9600 |
C6D—C21D | 1.54 (2) | C23P—H23H | 0.9600 |
C7D—C22D | 1.52 (2) | C23P—H23I | 0.9600 |
C7D—C8D | 1.53 (2) | N1—C25 | 1.503 (4) |
C8D—C13D | 1.38 (2) | N1—H1A | 0.8900 |
C8D—C9D | 1.40 (2) | N1—H1B | 0.8900 |
C9D—C10D | 1.41 (2) | N1—H1C | 0.8900 |
C9D—H9D | 0.9300 | C24—C25 | 1.521 (5) |
C10D—C11D | 1.41 (2) | C24—H24A | 0.9600 |
C10D—H10D | 0.9300 | C24—H24B | 0.9600 |
C11D—C12D | 1.39 (2) | C24—H24C | 0.9600 |
C11D—C14D | 1.49 (2) | C25—C26 | 1.510 (5) |
C12D—C13D | 1.38 (2) | C25—H25 | 0.9800 |
C12D—H12D | 0.9300 | C26—C27 | 1.378 (5) |
C13D—H13D | 0.9300 | C26—C31 | 1.390 (5) |
C15D—C16D | 1.50 (3) | C27—C28 | 1.388 (6) |
C15D—C17D | 1.54 (3) | C27—H27 | 0.9300 |
C15D—H15D | 0.9800 | C28—C29 | 1.360 (8) |
C16D—H16D | 0.9600 | C28—H28 | 0.9300 |
C16D—H16E | 0.9600 | C29—C30 | 1.362 (8) |
C16D—H16F | 0.9600 | C29—H29 | 0.9300 |
C17D—H17D | 0.9600 | C30—C31 | 1.392 (6) |
C17D—H17E | 0.9600 | C30—H30 | 0.9300 |
C17D—H17F | 0.9600 | C31—H31 | 0.9300 |
C18D—C19D | 1.52 (3) | ||
C2—C1—C6 | 120.8 (7) | C18D—C19D—H19D | 109.5 |
C2—C1—C7 | 118.0 (7) | C18D—C19D—H19E | 109.5 |
C6—C1—C7 | 121.3 (7) | H19D—C19D—H19E | 109.5 |
C1—C2—C3 | 118.9 (8) | C18D—C19D—H19F | 109.5 |
C1—C2—C15 | 121.9 (8) | H19D—C19D—H19F | 109.5 |
C3—C2—C15 | 119.2 (9) | H19E—C19D—H19F | 109.5 |
C4—C3—C2 | 122.5 (9) | C18D—C20D—H20D | 109.5 |
C4—C3—H3 | 118.7 | C18D—C20D—H20E | 109.5 |
C2—C3—H3 | 118.7 | H20D—C20D—H20E | 109.5 |
C3—C4—C5 | 116.9 (8) | C18D—C20D—H20F | 109.5 |
C3—C4—C18 | 123.5 (10) | H20D—C20D—H20F | 109.5 |
C5—C4—C18 | 119.6 (9) | H20E—C20D—H20F | 109.5 |
C4—C5—C6 | 123.7 (9) | C23D—C21D—C22D | 122 (3) |
C4—C5—H5 | 118.1 | C23D—C21D—C6D | 116 (3) |
C6—C5—H5 | 118.1 | C22D—C21D—C6D | 99 (2) |
C1—C6—C5 | 117.1 (8) | C23D—C21D—H21D | 106.4 |
C1—C6—C21 | 120.2 (7) | C22D—C21D—H21D | 106.4 |
C5—C6—C21 | 122.6 (8) | C6D—C21D—H21D | 106.4 |
O1—C7—C8 | 121.2 (6) | C21D—C22D—C7D | 110.5 (18) |
O1—C7—C1 | 120.1 (6) | C21D—C22D—H22D | 109.5 |
C8—C7—C1 | 118.7 (6) | C7D—C22D—H22D | 109.5 |
C13—C8—C9 | 117.0 (6) | C21D—C22D—H22E | 109.5 |
C13—C8—C7 | 124.6 (6) | C7D—C22D—H22E | 109.5 |
C9—C8—C7 | 118.3 (6) | H22D—C22D—H22E | 108.1 |
C10—C9—C8 | 122.6 (7) | C21D—C23D—H23D | 109.5 |
C10—C9—H9 | 118.7 | C21D—C23D—H23E | 109.5 |
C8—C9—H9 | 118.7 | H23D—C23D—H23E | 109.5 |
C11—C10—C9 | 119.3 (6) | C21D—C23D—H23F | 109.5 |
C11—C10—H10 | 120.4 | H23D—C23D—H23F | 109.5 |
C9—C10—H10 | 120.4 | H23E—C23D—H23F | 109.5 |
C10—C11—C12 | 119.6 (6) | C6P—C1P—C2P | 120 (2) |
C10—C11—C14 | 121.0 (6) | C6P—C1P—C7P | 147 (3) |
C12—C11—C14 | 119.5 (7) | C2P—C1P—C7P | 92 (2) |
C13—C12—C11 | 119.7 (6) | C3P—C2P—C1P | 117 (3) |
C13—C12—H12 | 120.1 | C3P—C2P—C15P | 143 (3) |
C11—C12—H12 | 120.1 | C1P—C2P—C15P | 99 (2) |
C8—C13—C12 | 121.6 (6) | C4P—C3P—C2P | 123 (3) |
C8—C13—H13 | 119.2 | C4P—C3P—H3P | 118.6 |
C12—C13—H13 | 119.2 | C2P—C3P—H3P | 118.6 |
O3—C14—O2 | 123.3 (3) | C3P—C4P—C5P | 121 (3) |
O3—C14—C11 | 118.5 (4) | C3P—C4P—C18P | 120 (3) |
O2—C14—C11 | 118.2 (4) | C5P—C4P—C18P | 118 (3) |
C2—C15—C16 | 111.3 (9) | C4P—C5P—C6P | 116 (3) |
C2—C15—C17 | 111.2 (9) | C4P—C5P—H5P | 122.0 |
C16—C15—C17 | 110.6 (9) | C6P—C5P—H5P | 122.0 |
C2—C15—H15 | 107.9 | C1P—C6P—C5P | 122 (3) |
C16—C15—H15 | 107.9 | C1P—C6P—C21P | 123 (3) |
C17—C15—H15 | 107.9 | C5P—C6P—C21P | 114 (3) |
C15—C16—H16A | 109.5 | O1P—C7P—C1P | 123 (3) |
C15—C16—H16B | 109.5 | O1P—C7P—C8P | 111 (2) |
H16A—C16—H16B | 109.5 | C1P—C7P—C8P | 115 (3) |
C15—C16—H16C | 109.5 | O1P—C7P—C15P | 109 (2) |
H16A—C16—H16C | 109.5 | C1P—C7P—C15P | 86.4 (18) |
H16B—C16—H16C | 109.5 | C8P—C7P—C15P | 106.7 (18) |
C15—C17—H17A | 109.5 | C9P—C8P—C13P | 116 (2) |
C15—C17—H17B | 109.5 | C9P—C8P—C7P | 122 (2) |
H17A—C17—H17B | 109.5 | C13P—C8P—C7P | 122 (2) |
C15—C17—H17C | 109.5 | C8P—C9P—C10P | 122 (3) |
H17A—C17—H17C | 109.5 | C8P—C9P—H9P | 119.0 |
H17B—C17—H17C | 109.5 | C10P—C9P—H9P | 119.0 |
C20—C18—C19 | 114.7 (7) | C11P—C10P—C9P | 123 (3) |
C20—C18—C4 | 112.8 (8) | C11P—C10P—H10P | 118.7 |
C19—C18—C4 | 116.3 (8) | C9P—C10P—H10P | 118.7 |
C20—C18—H18 | 103.7 | C10P—C11P—C12P | 116 (2) |
C19—C18—H18 | 103.7 | C10P—C11P—C14P | 119 (2) |
C4—C18—H18 | 103.7 | C12P—C11P—C14P | 125 (3) |
C18—C19—H19A | 109.5 | C11P—C12P—C13P | 121 (3) |
C18—C19—H19B | 109.5 | C11P—C12P—H12P | 119.3 |
H19A—C19—H19B | 109.5 | C13P—C12P—H12P | 119.3 |
C18—C19—H19C | 109.5 | C8P—C13P—C12P | 122 (3) |
H19A—C19—H19C | 109.5 | C8P—C13P—H13P | 119.1 |
H19B—C19—H19C | 109.5 | C12P—C13P—H13P | 119.1 |
C18—C20—H20A | 109.5 | O3P—C14P—O2P | 123.3 (3) |
C18—C20—H20B | 109.5 | O3P—C14P—C11P | 115.0 (15) |
H20A—C20—H20B | 109.5 | O2P—C14P—C11P | 120.5 (15) |
C18—C20—H20C | 109.5 | C2P—C15P—C16P | 120 (3) |
H20A—C20—H20C | 109.5 | C2P—C15P—C17P | 120 (4) |
H20B—C20—H20C | 109.5 | C16P—C15P—C17P | 110 (3) |
C6—C21—C22 | 111.4 (9) | C2P—C15P—C7P | 82.8 (18) |
C6—C21—C23 | 113.3 (8) | C16P—C15P—C7P | 108 (3) |
C22—C21—C23 | 110.5 (6) | C17P—C15P—C7P | 114 (3) |
C6—C21—H21 | 107.1 | C15P—C16P—H16G | 109.5 |
C22—C21—H21 | 107.1 | C15P—C16P—H16H | 109.5 |
C23—C21—H21 | 107.1 | H16G—C16P—H16H | 109.5 |
C21—C22—H22A | 109.5 | C15P—C16P—H16I | 109.5 |
C21—C22—H22B | 109.5 | H16G—C16P—H16I | 109.5 |
H22A—C22—H22B | 109.5 | H16H—C16P—H16I | 109.5 |
C21—C22—H22C | 109.5 | C15P—C17P—H17G | 109.5 |
H22A—C22—H22C | 109.5 | C15P—C17P—H17H | 109.5 |
H22B—C22—H22C | 109.5 | H17G—C17P—H17H | 109.5 |
C21—C23—H23A | 109.5 | C15P—C17P—H17I | 109.5 |
C21—C23—H23B | 109.5 | H17G—C17P—H17I | 109.5 |
H23A—C23—H23B | 109.5 | H17H—C17P—H17I | 109.5 |
C21—C23—H23C | 109.5 | C20P—C18P—C19P | 115 (4) |
H23A—C23—H23C | 109.5 | C20P—C18P—C4P | 104 (3) |
H23B—C23—H23C | 109.5 | C19P—C18P—C4P | 108 (3) |
C2D—C1D—C6D | 120 (2) | C20P—C18P—H18P | 110.1 |
C2D—C1D—C7D | 131 (2) | C19P—C18P—H18P | 110.1 |
C6D—C1D—C7D | 108 (2) | C4P—C18P—H18P | 110.1 |
C1D—C2D—C3D | 118 (3) | C18P—C19P—H19G | 109.5 |
C1D—C2D—C15D | 123 (3) | C18P—C19P—H19H | 109.5 |
C3D—C2D—C15D | 119 (3) | H19G—C19P—H19H | 109.5 |
C2D—C3D—C4D | 122 (3) | C18P—C19P—H19I | 109.5 |
C2D—C3D—H3D | 119.0 | H19G—C19P—H19I | 109.5 |
C4D—C3D—H3D | 119.0 | H19H—C19P—H19I | 109.5 |
C5D—C4D—C3D | 118 (3) | C18P—C20P—H20G | 109.5 |
C5D—C4D—C18D | 116 (3) | C18P—C20P—H20H | 109.5 |
C3D—C4D—C18D | 126 (3) | H20G—C20P—H20H | 109.5 |
C6D—C5D—C4D | 119 (3) | C18P—C20P—H20I | 109.5 |
C6D—C5D—H5D | 120.4 | H20G—C20P—H20I | 109.5 |
C4D—C5D—H5D | 120.4 | H20H—C20P—H20I | 109.5 |
C5D—C6D—C1D | 122 (3) | C6P—C21P—C22P | 109 (4) |
C5D—C6D—C21D | 124 (2) | C6P—C21P—C23P | 111 (4) |
C1D—C6D—C21D | 113 (2) | C22P—C21P—C23P | 107 (4) |
O1D—C7D—C22D | 106 (2) | C6P—C21P—H21P | 110.0 |
O1D—C7D—C8D | 106 (2) | C22P—C21P—H21P | 110.0 |
C22D—C7D—C8D | 115 (2) | C23P—C21P—H21P | 110.0 |
O1D—C7D—C1D | 109 (3) | C21P—C22P—H22F | 109.5 |
C22D—C7D—C1D | 101.5 (18) | C21P—C22P—H22G | 109.5 |
C8D—C7D—C1D | 118 (3) | H22F—C22P—H22G | 109.5 |
C13D—C8D—C9D | 121 (2) | C21P—C22P—H22H | 109.5 |
C13D—C8D—C7D | 115 (2) | H22F—C22P—H22H | 109.5 |
C9D—C8D—C7D | 124 (2) | H22G—C22P—H22H | 109.5 |
C8D—C9D—C10D | 115 (2) | C21P—C23P—H23G | 109.5 |
C8D—C9D—H9D | 122.6 | C21P—C23P—H23H | 109.5 |
C10D—C9D—H9D | 122.6 | H23G—C23P—H23H | 109.5 |
C11D—C10D—C9D | 126 (2) | C21P—C23P—H23I | 109.5 |
C11D—C10D—H10D | 117.1 | H23G—C23P—H23I | 109.5 |
C9D—C10D—H10D | 117.1 | H23H—C23P—H23I | 109.5 |
C12D—C11D—C10D | 115 (2) | C25—N1—H1A | 109.5 |
C12D—C11D—C14D | 119 (2) | C25—N1—H1B | 109.5 |
C10D—C11D—C14D | 125 (2) | H1A—N1—H1B | 109.5 |
C13D—C12D—C11D | 121 (3) | C25—N1—H1C | 109.5 |
C13D—C12D—H12D | 119.3 | H1A—N1—H1C | 109.5 |
C11D—C12D—H12D | 119.3 | H1B—N1—H1C | 109.5 |
C8D—C13D—C12D | 121 (2) | C25—C24—H24A | 109.5 |
C8D—C13D—H13D | 119.3 | C25—C24—H24B | 109.5 |
C12D—C13D—H13D | 119.3 | H24A—C24—H24B | 109.5 |
O3D—C14D—O2D | 123.3 (3) | C25—C24—H24C | 109.5 |
O3D—C14D—C11D | 121.2 (13) | H24A—C24—H24C | 109.5 |
O2D—C14D—C11D | 115.4 (13) | H24B—C24—H24C | 109.5 |
C16D—C15D—C2D | 113 (3) | N1—C25—C26 | 110.1 (2) |
C16D—C15D—C17D | 115 (3) | N1—C25—C24 | 109.0 (3) |
C2D—C15D—C17D | 112 (3) | C26—C25—C24 | 115.1 (3) |
C16D—C15D—H15D | 105.5 | N1—C25—H25 | 107.4 |
C2D—C15D—H15D | 105.5 | C26—C25—H25 | 107.4 |
C17D—C15D—H15D | 105.5 | C24—C25—H25 | 107.4 |
C15D—C16D—H16D | 109.5 | C27—C26—C31 | 118.0 (4) |
C15D—C16D—H16E | 109.5 | C27—C26—C25 | 120.7 (3) |
H16D—C16D—H16E | 109.5 | C31—C26—C25 | 121.3 (3) |
C15D—C16D—H16F | 109.5 | C26—C27—C28 | 121.0 (5) |
H16D—C16D—H16F | 109.5 | C26—C27—H27 | 119.5 |
H16E—C16D—H16F | 109.5 | C28—C27—H27 | 119.5 |
C15D—C17D—H17D | 109.5 | C29—C28—C27 | 120.4 (5) |
C15D—C17D—H17E | 109.5 | C29—C28—H28 | 119.8 |
H17D—C17D—H17E | 109.5 | C27—C28—H28 | 119.8 |
C15D—C17D—H17F | 109.5 | C28—C29—C30 | 119.8 (5) |
H17D—C17D—H17F | 109.5 | C28—C29—H29 | 120.1 |
H17E—C17D—H17F | 109.5 | C30—C29—H29 | 120.1 |
C19D—C18D—C20D | 108 (3) | C29—C30—C31 | 120.6 (5) |
C19D—C18D—C4D | 111 (3) | C29—C30—H30 | 119.7 |
C20D—C18D—C4D | 109 (3) | C31—C30—H30 | 119.7 |
C19D—C18D—H18D | 109.6 | C26—C31—C30 | 120.2 (5) |
C20D—C18D—H18D | 109.6 | C26—C31—H31 | 119.9 |
C4D—C18D—H18D | 109.6 | C30—C31—H31 | 119.9 |
C31H39NO3 | Dx = 1.250 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 1031 reflections |
a = 5.9414 (8) Å | θ = 5.6–21.7° |
b = 13.381 (3) Å | µ = 0.08 mm−1 |
c = 31.662 (18) Å | T = 299 K |
V = 2517.2 (16) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.10 × 0.08 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 2091 independent reflections |
Radiation source: fine-focus sealed tube | 1073 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.090 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 24.6°, θmin = 5.6° |
φ– and ω scans | h = −6→6 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −11→15 |
Tmin = 0.334, Tmax = 1.000 | l = −19→22 |
5484 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.068 | w = 1/[σ2(Fo2) + (0.0585P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.164 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.16 e Å−3 |
2091 reflections | Δρmin = −0.19 e Å−3 |
264 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
0 restraints | Absolute structure parameter: 1.6 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.0568 (13) | 0.2206 (6) | 0.6295 (4) | 0.083 (5) | |
O2 | 0.6131 (11) | 0.6246 (6) | 0.5177 (4) | 0.055 (5) | |
O3 | 0.3025 (11) | 0.6156 (6) | 0.5557 (4) | 0.069 (5) | |
N1 | 0.0415 (13) | 0.6715 (7) | 0.4901 (6) | 0.054 (7) | |
H1A | 0.1554 | 0.6577 | 0.5074 | 0.065* | |
H1B | −0.0846 | 0.6449 | 0.5003 | 0.065* | |
H1C | 0.0255 | 0.7375 | 0.4880 | 0.065* | |
C1 | 0.8226 (17) | 0.2537 (9) | 0.6880 (7) | 0.043 (3)* | |
C2 | 0.9051 (16) | 0.3186 (8) | 0.7206 (6) | 0.044 (3)* | |
C3 | 0.8454 (15) | 0.3033 (8) | 0.7613 (7) | 0.049 (4)* | |
H3 | 0.9019 | 0.3459 | 0.7819 | 0.059* | |
C4 | 0.7033 (18) | 0.2268 (9) | 0.7732 (7) | 0.049 (4)* | |
C5 | 0.6178 (15) | 0.1643 (8) | 0.7414 (6) | 0.042 (3)* | |
H5 | 0.5181 | 0.1138 | 0.7490 | 0.050* | |
C6 | 0.6745 (16) | 0.1744 (8) | 0.6998 (7) | 0.042 (3)* | |
C7 | 0.900 (2) | 0.2662 (9) | 0.6435 (8) | 0.069 (9) | |
C8 | 0.7878 (15) | 0.3448 (8) | 0.6163 (6) | 0.040 (3)* | |
C9 | 0.8961 (17) | 0.3826 (8) | 0.5832 (5) | 0.046 (3)* | |
H9 | 1.0368 | 0.3575 | 0.5759 | 0.055* | |
C10 | 0.8020 (15) | 0.4588 (8) | 0.5596 (6) | 0.052 (3)* | |
H10 | 0.8766 | 0.4829 | 0.5358 | 0.063* | |
C11 | 0.5966 (16) | 0.4992 (8) | 0.5713 (6) | 0.048 (3)* | |
C12 | 0.4828 (16) | 0.4611 (8) | 0.6057 (6) | 0.047 (3)* | |
H12 | 0.3430 | 0.4869 | 0.6132 | 0.057* | |
C13 | 0.5769 (16) | 0.3841 (8) | 0.6294 (5) | 0.053 (3)* | |
H13 | 0.5038 | 0.3591 | 0.6531 | 0.064* | |
C14 | 0.4959 (19) | 0.5854 (9) | 0.5459 (7) | 0.054 (8) | |
C15 | 1.0590 (14) | 0.4053 (7) | 0.7077 (6) | 0.067 (8) | |
H15 | 1.0866 | 0.3989 | 0.6773 | 0.080* | |
C16 | 1.2839 (15) | 0.4023 (9) | 0.7293 (7) | 0.059 (7) | |
H16A | 1.3493 | 0.3372 | 0.7258 | 0.089* | |
H16B | 1.2651 | 0.4163 | 0.7588 | 0.089* | |
H16C | 1.3812 | 0.4515 | 0.7169 | 0.089* | |
C17 | 0.936 (2) | 0.5046 (8) | 0.7146 (6) | 0.071 (8) | |
H17A | 0.9217 | 0.5171 | 0.7444 | 0.107* | |
H17B | 0.7889 | 0.5011 | 0.7021 | 0.107* | |
H17C | 1.0199 | 0.5577 | 0.7017 | 0.107* | |
C18 | 0.6375 (19) | 0.2073 (10) | 0.8187 (8) | 0.071 (8) | |
H18 | 0.6542 | 0.1349 | 0.8222 | 0.085* | |
C19 | 0.7912 (18) | 0.2526 (10) | 0.8525 (7) | 0.070 (8) | |
H19A | 0.7617 | 0.3229 | 0.8549 | 0.104* | |
H19B | 0.9457 | 0.2425 | 0.8447 | 0.104* | |
H19C | 0.7627 | 0.2208 | 0.8792 | 0.104* | |
C20 | 0.3938 (17) | 0.2273 (11) | 0.8281 (9) | 0.100 (9) | |
H20A | 0.3524 | 0.1941 | 0.8539 | 0.149* | |
H20B | 0.3026 | 0.2027 | 0.8054 | 0.149* | |
H20C | 0.3708 | 0.2980 | 0.8312 | 0.149* | |
C21 | 0.5820 (16) | 0.1039 (8) | 0.6665 (6) | 0.050 (6) | |
H21 | 0.5543 | 0.1428 | 0.6408 | 0.060* | |
C22 | 0.760 (2) | 0.0241 (9) | 0.6562 (7) | 0.070 (8) | |
H22A | 0.7951 | −0.0132 | 0.6812 | 0.104* | |
H22B | 0.8940 | 0.0560 | 0.6458 | 0.104* | |
H22C | 0.7024 | −0.0204 | 0.6350 | 0.104* | |
C23 | 0.3647 (17) | 0.0525 (9) | 0.6786 (8) | 0.070 (8) | |
H23A | 0.2567 | 0.1016 | 0.6874 | 0.105* | |
H23B | 0.3925 | 0.0067 | 0.7013 | 0.105* | |
H23C | 0.3070 | 0.0165 | 0.6547 | 0.105* | |
C24 | 0.3130 (16) | 0.6686 (9) | 0.4299 (8) | 0.076 (8) | |
H24A | 0.4330 | 0.6480 | 0.4482 | 0.113* | |
H24B | 0.3068 | 0.7402 | 0.4290 | 0.113* | |
H24C | 0.3394 | 0.6431 | 0.4020 | 0.113* | |
C25 | 0.0897 (18) | 0.6278 (11) | 0.4465 (7) | 0.046 (8) | |
H25 | −0.0292 | 0.6510 | 0.4275 | 0.056* | |
C26 | 0.0690 (18) | 0.5160 (9) | 0.4499 (6) | 0.062 (8) | |
C27 | −0.1310 (17) | 0.4689 (11) | 0.4405 (7) | 0.080 (9) | |
H27 | −0.2537 | 0.5064 | 0.4314 | 0.096* | |
C28 | −0.151 (2) | 0.3659 (13) | 0.4443 (7) | 0.091 (10) | |
H28 | −0.2861 | 0.3351 | 0.4376 | 0.109* | |
C29 | 0.027 (3) | 0.3091 (11) | 0.4580 (7) | 0.073 (8) | |
H29 | 0.0115 | 0.2402 | 0.4603 | 0.088* | |
C30 | 0.223 (2) | 0.3531 (12) | 0.4680 (7) | 0.070 (8) | |
H30 | 0.3435 | 0.3146 | 0.4774 | 0.085* | |
C31 | 0.2455 (18) | 0.4556 (12) | 0.4644 (7) | 0.062 (8) | |
H31 | 0.3814 | 0.4853 | 0.4719 | 0.074* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.084 (5) | 0.088 (8) | 0.076 (18) | 0.048 (5) | 0.028 (7) | 0.029 (6) |
O2 | 0.051 (4) | 0.051 (6) | 0.064 (16) | −0.002 (4) | −0.007 (6) | 0.009 (6) |
O3 | 0.055 (4) | 0.075 (6) | 0.077 (16) | 0.023 (4) | 0.004 (6) | 0.014 (6) |
N1 | 0.040 (5) | 0.048 (8) | 0.07 (3) | 0.002 (4) | 0.000 (8) | 0.014 (8) |
C7 | 0.053 (7) | 0.052 (10) | 0.10 (3) | −0.001 (7) | −0.001 (11) | 0.016 (9) |
C14 | 0.043 (6) | 0.039 (9) | 0.08 (3) | −0.002 (6) | −0.004 (9) | 0.006 (8) |
C15 | 0.039 (5) | 0.035 (8) | 0.13 (3) | −0.001 (5) | 0.003 (8) | −0.010 (8) |
C16 | 0.059 (6) | 0.052 (9) | 0.07 (2) | 0.002 (5) | −0.005 (9) | −0.002 (8) |
C17 | 0.059 (6) | 0.056 (10) | 0.10 (3) | 0.001 (6) | 0.021 (9) | 0.003 (9) |
C18 | 0.051 (7) | 0.069 (11) | 0.09 (3) | 0.006 (6) | −0.001 (11) | −0.010 (10) |
C19 | 0.068 (7) | 0.096 (12) | 0.04 (3) | −0.002 (7) | −0.012 (11) | 0.009 (10) |
C20 | 0.057 (7) | 0.114 (14) | 0.13 (3) | 0.000 (7) | 0.007 (11) | −0.004 (11) |
C21 | 0.052 (6) | 0.049 (9) | 0.05 (2) | −0.006 (6) | −0.002 (9) | −0.007 (7) |
C22 | 0.077 (7) | 0.053 (11) | 0.08 (3) | −0.006 (6) | 0.003 (10) | −0.014 (9) |
C23 | 0.069 (7) | 0.057 (10) | 0.08 (3) | −0.023 (6) | −0.011 (10) | 0.004 (9) |
C24 | 0.067 (7) | 0.060 (10) | 0.10 (3) | −0.015 (6) | 0.017 (10) | −0.002 (9) |
C25 | 0.047 (6) | 0.074 (13) | 0.02 (3) | −0.007 (6) | 0.002 (9) | 0.010 (10) |
C26 | 0.057 (7) | 0.045 (10) | 0.09 (3) | −0.004 (6) | 0.016 (9) | 0.003 (8) |
C27 | 0.053 (7) | 0.066 (12) | 0.12 (3) | −0.011 (7) | 0.009 (9) | −0.016 (11) |
C28 | 0.080 (9) | 0.072 (13) | 0.12 (3) | −0.034 (9) | 0.030 (12) | −0.020 (12) |
C29 | 0.105 (11) | 0.064 (11) | 0.05 (3) | −0.008 (10) | 0.028 (11) | −0.012 (9) |
C30 | 0.086 (9) | 0.052 (13) | 0.07 (3) | −0.001 (8) | 0.010 (10) | −0.001 (9) |
C31 | 0.055 (7) | 0.076 (13) | 0.06 (3) | −0.006 (7) | −0.003 (9) | −0.002 (9) |
O1—C7 | 1.198 (16) | C17—H17B | 0.9600 |
O2—C14 | 1.247 (18) | C17—H17C | 0.9600 |
O3—C14 | 1.257 (13) | C18—C20 | 1.502 (16) |
N1—C25 | 1.53 (2) | C18—C19 | 1.53 (2) |
N1—H1A | 0.8900 | C18—H18 | 0.9800 |
N1—H1B | 0.8900 | C19—H19A | 0.9600 |
N1—H1C | 0.8900 | C19—H19B | 0.9600 |
C1—C6 | 1.429 (17) | C19—H19C | 0.9600 |
C1—C2 | 1.43 (2) | C20—H20A | 0.9600 |
C1—C7 | 1.49 (3) | C20—H20B | 0.9600 |
C2—C3 | 1.35 (2) | C20—H20C | 0.9600 |
C2—C15 | 1.531 (15) | C21—C23 | 1.512 (15) |
C3—C4 | 1.381 (16) | C21—C22 | 1.539 (14) |
C3—H3 | 0.9300 | C21—H21 | 0.9800 |
C4—C5 | 1.40 (2) | C22—H22A | 0.9600 |
C4—C18 | 1.51 (3) | C22—H22B | 0.9600 |
C5—C6 | 1.37 (2) | C22—H22C | 0.9600 |
C5—H5 | 0.9300 | C23—H23A | 0.9600 |
C6—C21 | 1.52 (2) | C23—H23B | 0.9600 |
C7—C8 | 1.51 (2) | C23—H23C | 0.9600 |
C8—C9 | 1.328 (19) | C24—C25 | 1.528 (16) |
C8—C13 | 1.421 (15) | C24—H24A | 0.9600 |
C9—C10 | 1.384 (17) | C24—H24B | 0.9600 |
C9—H9 | 0.9300 | C24—H24C | 0.9600 |
C10—C11 | 1.385 (14) | C25—C26 | 1.506 (17) |
C10—H10 | 0.9300 | C25—H25 | 0.9800 |
C11—C12 | 1.38 (2) | C26—C27 | 1.378 (16) |
C11—C14 | 1.528 (19) | C26—C31 | 1.401 (15) |
C12—C13 | 1.389 (17) | C27—C28 | 1.388 (17) |
C12—H12 | 0.9300 | C27—H27 | 0.9300 |
C13—H13 | 0.9300 | C28—C29 | 1.37 (2) |
C15—C16 | 1.500 (16) | C28—H28 | 0.9300 |
C15—C17 | 1.532 (13) | C29—C30 | 1.343 (18) |
C15—H15 | 0.9800 | C29—H29 | 0.9300 |
C16—H16A | 0.9600 | C30—C31 | 1.383 (16) |
C16—H16B | 0.9600 | C30—H30 | 0.9300 |
C16—H16C | 0.9600 | C31—H31 | 0.9300 |
C17—H17A | 0.9600 | ||
C25—N1—H1A | 109.5 | C20—C18—C4 | 114.0 (18) |
C25—N1—H1B | 109.5 | C20—C18—C19 | 111.4 (17) |
H1A—N1—H1B | 109.5 | C4—C18—C19 | 116.2 (13) |
C25—N1—H1C | 109.5 | C20—C18—H18 | 104.6 |
H1A—N1—H1C | 109.5 | C4—C18—H18 | 104.6 |
H1B—N1—H1C | 109.5 | C19—C18—H18 | 104.6 |
C6—C1—C2 | 118.2 (18) | C18—C19—H19A | 109.5 |
C6—C1—C7 | 121.3 (15) | C18—C19—H19B | 109.5 |
C2—C1—C7 | 120.4 (13) | H19A—C19—H19B | 109.5 |
C3—C2—C1 | 120.2 (13) | C18—C19—H19C | 109.5 |
C3—C2—C15 | 121.6 (14) | H19A—C19—H19C | 109.5 |
C1—C2—C15 | 118.1 (16) | H19B—C19—H19C | 109.5 |
C2—C3—C4 | 122.3 (16) | C18—C20—H20A | 109.5 |
C2—C3—H3 | 118.8 | C18—C20—H20B | 109.5 |
C4—C3—H3 | 118.8 | H20A—C20—H20B | 109.5 |
C3—C4—C5 | 117.8 (19) | C18—C20—H20C | 109.5 |
C3—C4—C18 | 123.1 (16) | H20A—C20—H20C | 109.5 |
C5—C4—C18 | 119.1 (13) | H20B—C20—H20C | 109.5 |
C6—C5—C4 | 122.9 (14) | C23—C21—C6 | 114.6 (15) |
C6—C5—H5 | 118.6 | C23—C21—C22 | 109.0 (9) |
C4—C5—H5 | 118.6 | C6—C21—C22 | 109.3 (11) |
C5—C6—C1 | 118.5 (15) | C23—C21—H21 | 107.9 |
C5—C6—C21 | 121.3 (12) | C6—C21—H21 | 107.9 |
C1—C6—C21 | 120.2 (18) | C22—C21—H21 | 107.9 |
O1—C7—C1 | 122.2 (14) | C21—C22—H22A | 109.5 |
O1—C7—C8 | 119 (2) | C21—C22—H22B | 109.5 |
C1—C7—C8 | 118.6 (14) | H22A—C22—H22B | 109.5 |
C9—C8—C13 | 121.1 (13) | C21—C22—H22C | 109.5 |
C9—C8—C7 | 119.9 (11) | H22A—C22—H22C | 109.5 |
C13—C8—C7 | 118.7 (16) | H22B—C22—H22C | 109.5 |
C8—C9—C10 | 120.7 (11) | C21—C23—H23A | 109.5 |
C8—C9—H9 | 119.6 | C21—C23—H23B | 109.5 |
C10—C9—H9 | 119.6 | H23A—C23—H23B | 109.5 |
C9—C10—C11 | 119.9 (15) | C21—C23—H23C | 109.5 |
C9—C10—H10 | 120.0 | H23A—C23—H23C | 109.5 |
C11—C10—H10 | 120.0 | H23B—C23—H23C | 109.5 |
C12—C11—C10 | 119.9 (13) | C25—C24—H24A | 109.5 |
C12—C11—C14 | 120.2 (11) | C25—C24—H24B | 109.5 |
C10—C11—C14 | 119.9 (15) | H24A—C24—H24B | 109.5 |
C11—C12—C13 | 120.1 (10) | C25—C24—H24C | 109.5 |
C11—C12—H12 | 119.9 | H24A—C24—H24C | 109.5 |
C13—C12—H12 | 119.9 | H24B—C24—H24C | 109.5 |
C12—C13—C8 | 118.2 (14) | C26—C25—N1 | 107.5 (15) |
C12—C13—H13 | 120.9 | C26—C25—C24 | 116.8 (11) |
C8—C13—H13 | 120.9 | N1—C25—C24 | 109.8 (13) |
O2—C14—O3 | 123.5 (13) | C26—C25—H25 | 107.5 |
O2—C14—C11 | 118.3 (10) | N1—C25—H25 | 107.5 |
O3—C14—C11 | 118.1 (15) | C24—C25—H25 | 107.5 |
C16—C15—C2 | 113.0 (12) | C27—C26—C31 | 116.9 (12) |
C16—C15—C17 | 112.5 (10) | C27—C26—C25 | 120.6 (12) |
C2—C15—C17 | 109.5 (9) | C31—C26—C25 | 122.4 (11) |
C16—C15—H15 | 107.1 | C26—C27—C28 | 120.5 (13) |
C2—C15—H15 | 107.1 | C26—C27—H27 | 119.8 |
C17—C15—H15 | 107.1 | C28—C27—H27 | 119.8 |
C15—C16—H16A | 109.5 | C29—C28—C27 | 120.9 (13) |
C15—C16—H16B | 109.5 | C29—C28—H28 | 119.5 |
H16A—C16—H16B | 109.5 | C27—C28—H28 | 119.5 |
C15—C16—H16C | 109.5 | C30—C29—C28 | 120.0 (14) |
H16A—C16—H16C | 109.5 | C30—C29—H29 | 120.0 |
H16B—C16—H16C | 109.5 | C28—C29—H29 | 120.0 |
C15—C17—H17A | 109.5 | C29—C30—C31 | 119.9 (13) |
C15—C17—H17B | 109.5 | C29—C30—H30 | 120.0 |
H17A—C17—H17B | 109.5 | C31—C30—H30 | 120.0 |
C15—C17—H17C | 109.5 | C30—C31—C26 | 121.8 (12) |
H17A—C17—H17C | 109.5 | C30—C31—H31 | 119.1 |
H17B—C17—H17C | 109.5 | C26—C31—H31 | 119.1 |
C31H39NO3 | Dx = 1.247 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 957 reflections |
a = 5.9654 (10) Å | θ = 5.6–22.5° |
b = 13.321 (4) Å | µ = 0.08 mm−1 |
c = 31.75 (2) Å | T = 299 K |
V = 2523.0 (18) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.10 × 0.08 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 2098 independent reflections |
Radiation source: fine-focus sealed tube | 1029 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.095 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 24.7°, θmin = 5.6° |
φ– and ω scans | h = −6→6 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −11→15 |
Tmin = 0.379, Tmax = 1.000 | l = −19→22 |
5503 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.075 | w = 1/[σ2(Fo2) + (0.0464P)2 + 0.6534P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.160 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.17 e Å−3 |
2098 reflections | Δρmin = −0.15 e Å−3 |
248 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
86 restraints | Absolute structure parameter: 0.6 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O2 | 0.3851 (12) | 0.6241 (6) | 0.4833 (4) | 0.060 (5) | |
O3 | 0.6953 (13) | 0.6142 (6) | 0.4448 (4) | 0.078 (5) | |
N1 | 0.9576 (13) | 0.6708 (7) | 0.5102 (6) | 0.056 (7) | |
H1A | 0.9602 | 0.7374 | 0.5121 | 0.068* | |
H1B | 0.8497 | 0.6522 | 0.4925 | 0.068* | |
H1C | 1.0892 | 0.6490 | 0.5007 | 0.068* | |
C1 | 0.1769 (16) | 0.2562 (8) | 0.3091 (5) | 0.046 (4)* | |
C2 | 0.0937 (16) | 0.3196 (8) | 0.2787 (6) | 0.042 (3)* | |
C3 | 0.1570 (15) | 0.3039 (8) | 0.2381 (6) | 0.047 (3)* | |
H3 | 0.1023 | 0.3472 | 0.2176 | 0.056* | |
C4 | 0.2989 (19) | 0.2268 (9) | 0.2256 (7) | 0.049 (4)* | |
C5 | 0.3819 (15) | 0.1653 (8) | 0.2582 (6) | 0.040 (3)* | |
H5 | 0.4814 | 0.1144 | 0.2510 | 0.048* | |
C6 | 0.3256 (16) | 0.1758 (8) | 0.3000 (6) | 0.041 (3)* | |
C8 | 0.2084 (16) | 0.3475 (8) | 0.3812 (6) | 0.048 (3)* | |
C9 | 0.1002 (18) | 0.3835 (8) | 0.4165 (5) | 0.052 (3)* | |
H9 | −0.0366 | 0.3561 | 0.4246 | 0.062* | |
C10 | 0.1945 (16) | 0.4598 (8) | 0.4399 (6) | 0.053 (3)* | |
H10 | 0.1207 | 0.4845 | 0.4635 | 0.064* | |
C11 | 0.4016 (17) | 0.5000 (8) | 0.4279 (6) | 0.048 (3)* | |
C12 | 0.5132 (17) | 0.4616 (8) | 0.3935 (6) | 0.051 (4)* | |
H12 | 0.6526 | 0.4875 | 0.3862 | 0.062* | |
C13 | 0.4211 (16) | 0.3855 (8) | 0.3700 (5) | 0.054 (3)* | |
H13 | 0.4979 | 0.3594 | 0.3470 | 0.064* | |
C14 | 0.502 (2) | 0.5857 (9) | 0.4549 (7) | 0.056 (7) | |
C15 | −0.0554 (15) | 0.4074 (8) | 0.2920 (6) | 0.065 (8) | |
H15 | −0.0815 | 0.4014 | 0.3224 | 0.078* | |
C16 | −0.2815 (14) | 0.4026 (8) | 0.2703 (6) | 0.054 (6) | |
H16A | −0.3502 | 0.3388 | 0.2759 | 0.081* | |
H16B | −0.3759 | 0.4553 | 0.2808 | 0.081* | |
H16C | −0.2617 | 0.4106 | 0.2405 | 0.081* | |
C17 | 0.0623 (17) | 0.5070 (8) | 0.2843 (6) | 0.077 (8) | |
H17A | 0.2044 | 0.5071 | 0.2985 | 0.116* | |
H17B | 0.0855 | 0.5161 | 0.2546 | 0.116* | |
H17C | −0.0287 | 0.5608 | 0.2950 | 0.116* | |
C18 | 0.3680 (19) | 0.2055 (10) | 0.1820 (8) | 0.068 (8) | |
H18 | 0.3549 | 0.1325 | 0.1792 | 0.081* | |
C19 | 0.2133 (19) | 0.2488 (11) | 0.1468 (7) | 0.076 (8) | |
H19A | 0.2724 | 0.2309 | 0.1197 | 0.115* | |
H19B | 0.0652 | 0.2216 | 0.1498 | 0.115* | |
H19C | 0.2072 | 0.3206 | 0.1492 | 0.115* | |
C20 | 0.6126 (17) | 0.2278 (10) | 0.1730 (7) | 0.091 (8) | |
H20A | 0.6454 | 0.2122 | 0.1441 | 0.136* | |
H20B | 0.6419 | 0.2976 | 0.1781 | 0.136* | |
H20C | 0.7054 | 0.1877 | 0.1911 | 0.136* | |
C24 | 0.6889 (16) | 0.6674 (9) | 0.5695 (6) | 0.072 (7) | |
H24A | 0.6968 | 0.7393 | 0.5706 | 0.108* | |
H24B | 0.5714 | 0.6475 | 0.5506 | 0.108* | |
H24C | 0.6579 | 0.6416 | 0.5972 | 0.108* | |
C25 | 0.9121 (19) | 0.6255 (11) | 0.5540 (8) | 0.054 (8) | |
H25 | 1.0298 | 0.6489 | 0.5731 | 0.065* | |
C26 | 0.9327 (16) | 0.5144 (9) | 0.5502 (6) | 0.054 (3)* | |
C27 | 0.7592 (17) | 0.4567 (10) | 0.5358 (6) | 0.064 (4)* | |
H27 | 0.6257 | 0.4868 | 0.5275 | 0.077* | |
C28 | 0.7822 (19) | 0.3524 (10) | 0.5337 (7) | 0.076 (5)* | |
H28 | 0.6601 | 0.3132 | 0.5258 | 0.091* | |
C29 | 0.978 (2) | 0.3084 (11) | 0.5427 (7) | 0.085 (5)* | |
H29 | 0.9953 | 0.2393 | 0.5398 | 0.102* | |
C30 | 1.151 (2) | 0.3660 (10) | 0.5563 (7) | 0.081 (4)* | |
H30 | 1.2853 | 0.3354 | 0.5638 | 0.097* | |
C31 | 1.1319 (18) | 0.4695 (9) | 0.5592 (7) | 0.068 (4)* | |
H31 | 1.2546 | 0.5081 | 0.5673 | 0.082* | |
O1 | −0.0640 (19) | 0.2233 (9) | 0.3686 (5) | 0.087 (6) | 0.909 (17) |
C7 | 0.099 (2) | 0.2680 (10) | 0.3550 (6) | 0.071 (7) | 0.909 (17) |
C21 | 0.4095 (17) | 0.1044 (10) | 0.3342 (6) | 0.052 (5) | 0.909 (17) |
H21 | 0.4371 | 0.1437 | 0.3598 | 0.062* | 0.909 (17) |
C22 | 0.230 (2) | 0.0242 (10) | 0.3445 (7) | 0.079 (8) | 0.909 (17) |
H22A | 0.2856 | −0.0199 | 0.3660 | 0.118* | 0.909 (17) |
H22B | 0.0960 | 0.0566 | 0.3542 | 0.118* | 0.909 (17) |
H22C | 0.1972 | −0.0139 | 0.3196 | 0.118* | 0.909 (17) |
C23 | 0.629 (2) | 0.0513 (10) | 0.3220 (8) | 0.087 (9) | 0.909 (17) |
H23A | 0.6742 | 0.0075 | 0.3445 | 0.130* | 0.909 (17) |
H23B | 0.6055 | 0.0128 | 0.2969 | 0.130* | 0.909 (17) |
H23C | 0.7434 | 0.1005 | 0.3171 | 0.130* | 0.909 (17) |
O1D | −0.130 (7) | 0.261 (7) | 0.360 (3) | 0.085 (18)* | 0.091 (17) |
C7D | 0.111 (7) | 0.257 (3) | 0.3571 (9) | 0.070 (17)* | 0.091 (17) |
C21D | 0.426 (12) | 0.141 (7) | 0.3420 (12) | 0.052 (17)* | 0.091 (17) |
H21D | 0.5399 | 0.1908 | 0.3499 | 0.063* | 0.091 (17) |
C22D | 0.223 (13) | 0.160 (4) | 0.3705 (18) | 0.060 (15)* | 0.091 (17) |
H22D | 0.1180 | 0.1043 | 0.3679 | 0.072* | 0.091 (17) |
H22E | 0.2708 | 0.1640 | 0.3996 | 0.072* | 0.091 (17) |
C23D | 0.54 (2) | 0.042 (9) | 0.342 (3) | 0.09 (2)* | 0.091 (17) |
H23E | 0.6625 | 0.0433 | 0.3222 | 0.136* | 0.091 (17) |
H23D | 0.5944 | 0.0268 | 0.3694 | 0.136* | 0.091 (17) |
H23F | 0.4345 | −0.0090 | 0.3332 | 0.136* | 0.091 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.053 (4) | 0.055 (6) | 0.072 (17) | 0.006 (4) | −0.002 (6) | −0.012 (6) |
O3 | 0.060 (4) | 0.077 (7) | 0.097 (16) | −0.024 (5) | 0.008 (7) | −0.018 (7) |
N1 | 0.046 (5) | 0.043 (8) | 0.08 (3) | 0.003 (5) | −0.007 (8) | −0.014 (8) |
C14 | 0.058 (8) | 0.036 (10) | 0.08 (3) | 0.001 (6) | −0.007 (10) | −0.008 (8) |
C15 | 0.054 (6) | 0.028 (9) | 0.11 (3) | 0.002 (6) | −0.002 (9) | 0.001 (8) |
C16 | 0.053 (6) | 0.054 (9) | 0.06 (2) | 0.002 (5) | −0.005 (9) | 0.005 (8) |
C17 | 0.059 (6) | 0.047 (10) | 0.13 (3) | −0.004 (6) | 0.003 (9) | −0.005 (9) |
C18 | 0.055 (8) | 0.067 (11) | 0.08 (3) | −0.003 (6) | 0.013 (11) | 0.019 (10) |
C19 | 0.080 (8) | 0.118 (13) | 0.03 (3) | −0.002 (9) | −0.002 (11) | 0.001 (10) |
C20 | 0.060 (8) | 0.110 (13) | 0.10 (3) | −0.010 (7) | −0.003 (10) | 0.002 (10) |
C24 | 0.071 (7) | 0.059 (10) | 0.09 (3) | 0.004 (6) | 0.021 (10) | −0.004 (8) |
C25 | 0.057 (7) | 0.087 (14) | 0.02 (3) | 0.003 (7) | 0.001 (10) | −0.012 (11) |
O1 | 0.099 (7) | 0.084 (9) | 0.077 (17) | −0.046 (7) | 0.022 (9) | −0.036 (8) |
C7 | 0.054 (7) | 0.064 (11) | 0.09 (2) | −0.006 (7) | 0.011 (11) | −0.011 (10) |
C21 | 0.057 (7) | 0.036 (9) | 0.063 (16) | 0.010 (7) | −0.013 (9) | 0.003 (8) |
C22 | 0.082 (9) | 0.069 (12) | 0.08 (3) | −0.008 (8) | 0.007 (12) | 0.009 (10) |
C23 | 0.071 (9) | 0.046 (11) | 0.14 (3) | 0.034 (8) | 0.014 (12) | 0.005 (10) |
O2—C14 | 1.250 (18) | C18—H18 | 0.9800 |
O3—C14 | 1.255 (14) | C19—H19A | 0.9600 |
N1—C25 | 1.54 (3) | C19—H19B | 0.9600 |
N1—H1A | 0.8900 | C19—H19C | 0.9600 |
N1—H1B | 0.8900 | C20—H20A | 0.9600 |
N1—H1C | 0.8900 | C20—H20B | 0.9600 |
C1—C2 | 1.375 (17) | C20—H20C | 0.9600 |
C1—C6 | 1.420 (14) | C24—C25 | 1.526 (16) |
C1—C7 | 1.536 (18) | C24—H24A | 0.9600 |
C1—C7D | 1.57 (3) | C24—H24B | 0.9600 |
C2—C3 | 1.36 (2) | C24—H24C | 0.9600 |
C2—C15 | 1.528 (15) | C25—C26 | 1.490 (18) |
C3—C4 | 1.388 (15) | C25—H25 | 0.9800 |
C3—H3 | 0.9300 | C26—C31 | 1.361 (15) |
C4—C5 | 1.41 (2) | C26—C27 | 1.367 (15) |
C4—C18 | 1.47 (3) | C27—C28 | 1.397 (14) |
C5—C6 | 1.37 (2) | C27—H27 | 0.9300 |
C5—H5 | 0.9300 | C28—C29 | 1.340 (15) |
C6—C21 | 1.528 (16) | C28—H28 | 0.9300 |
C6—C21D | 1.53 (3) | C29—C30 | 1.355 (17) |
C8—C9 | 1.380 (19) | C29—H29 | 0.9300 |
C8—C13 | 1.411 (15) | C30—C31 | 1.387 (15) |
C8—C7 | 1.496 (16) | C30—H30 | 0.9300 |
C8—C7D | 1.54 (2) | C31—H31 | 0.9300 |
C9—C10 | 1.379 (16) | O1—C7 | 1.221 (13) |
C9—H9 | 0.9300 | C21—C23 | 1.536 (14) |
C10—C11 | 1.399 (14) | C21—C22 | 1.547 (15) |
C10—H10 | 0.9300 | C21—H21 | 0.9800 |
C11—C12 | 1.38 (2) | C22—H22A | 0.9600 |
C11—C14 | 1.548 (19) | C22—H22B | 0.9600 |
C12—C13 | 1.374 (16) | C22—H22C | 0.9600 |
C12—H12 | 0.9300 | C23—H23A | 0.9600 |
C13—H13 | 0.9300 | C23—H23B | 0.9600 |
C15—C16 | 1.515 (15) | C23—H23C | 0.9600 |
C15—C17 | 1.521 (13) | O1D—C7D | 1.44 (3) |
C15—H15 | 0.9800 | C7D—C22D | 1.53 (3) |
C16—H16A | 0.9600 | C21D—C23D | 1.49 (3) |
C16—H16B | 0.9600 | C21D—C22D | 1.53 (3) |
C16—H16C | 0.9600 | C21D—H21D | 0.9800 |
C17—H17A | 0.9600 | C22D—H22D | 0.9700 |
C17—H17B | 0.9600 | C22D—H22E | 0.9700 |
C17—H17C | 0.9600 | C23D—H23E | 0.9600 |
C18—C20 | 1.516 (15) | C23D—H23D | 0.9600 |
C18—C19 | 1.56 (2) | C23D—H23F | 0.9600 |
C25—N1—H1A | 109.5 | C18—C20—H20A | 109.5 |
C25—N1—H1B | 109.5 | C18—C20—H20B | 109.5 |
H1A—N1—H1B | 109.5 | H20A—C20—H20B | 109.5 |
C25—N1—H1C | 109.5 | C18—C20—H20C | 109.5 |
H1A—N1—H1C | 109.5 | H20A—C20—H20C | 109.5 |
H1B—N1—H1C | 109.5 | H20B—C20—H20C | 109.5 |
C2—C1—C6 | 123.1 (15) | C25—C24—H24A | 109.5 |
C2—C1—C7 | 119.5 (12) | C25—C24—H24B | 109.5 |
C6—C1—C7 | 117.3 (12) | H24A—C24—H24B | 109.5 |
C2—C1—C7D | 126 (2) | C25—C24—H24C | 109.5 |
C6—C1—C7D | 111 (2) | H24A—C24—H24C | 109.5 |
C3—C2—C1 | 118.0 (12) | H24B—C24—H24C | 109.5 |
C3—C2—C15 | 122.8 (13) | C26—C25—C24 | 117.5 (11) |
C1—C2—C15 | 119.1 (15) | C26—C25—N1 | 107.6 (16) |
C2—C3—C4 | 123.7 (16) | C24—C25—N1 | 107.6 (13) |
C2—C3—H3 | 118.2 | C26—C25—H25 | 107.9 |
C4—C3—H3 | 118.2 | C24—C25—H25 | 107.9 |
C3—C4—C5 | 115.7 (19) | N1—C25—H25 | 107.9 |
C3—C4—C18 | 125.6 (16) | C31—C26—C27 | 119.0 (12) |
C5—C4—C18 | 118.7 (13) | C31—C26—C25 | 119.4 (11) |
C6—C5—C4 | 124.3 (13) | C27—C26—C25 | 121.5 (11) |
C6—C5—H5 | 117.9 | C26—C27—C28 | 120.1 (12) |
C4—C5—H5 | 117.9 | C26—C27—H27 | 120.0 |
C5—C6—C1 | 115.2 (12) | C28—C27—H27 | 120.0 |
C5—C6—C21 | 122.9 (12) | C29—C28—C27 | 120.7 (13) |
C1—C6—C21 | 121.9 (15) | C29—C28—H28 | 119.6 |
C5—C6—C21D | 135 (2) | C27—C28—H28 | 119.6 |
C1—C6—C21D | 107 (2) | C28—C29—C30 | 119.0 (14) |
C9—C8—C13 | 120.0 (13) | C28—C29—H29 | 120.5 |
C9—C8—C7 | 119.6 (10) | C30—C29—H29 | 120.5 |
C13—C8—C7 | 120.3 (14) | C29—C30—C31 | 121.5 (13) |
C9—C8—C7D | 119.9 (15) | C29—C30—H30 | 119.3 |
C13—C8—C7D | 119.6 (18) | C31—C30—H30 | 119.3 |
C10—C9—C8 | 120.2 (11) | C26—C31—C30 | 119.6 (13) |
C10—C9—H9 | 119.9 | C26—C31—H31 | 120.2 |
C8—C9—H9 | 119.9 | C30—C31—H31 | 120.2 |
C9—C10—C11 | 119.8 (15) | O1—C7—C8 | 119.7 (15) |
C9—C10—H10 | 120.1 | O1—C7—C1 | 121.7 (13) |
C11—C10—H10 | 120.1 | C8—C7—C1 | 118.0 (12) |
C12—C11—C10 | 120.0 (13) | C6—C21—C23 | 112.7 (14) |
C12—C11—C14 | 121.6 (11) | C6—C21—C22 | 110.7 (11) |
C10—C11—C14 | 118.3 (15) | C23—C21—C22 | 108.9 (11) |
C13—C12—C11 | 120.8 (11) | C6—C21—H21 | 108.1 |
C13—C12—H12 | 119.6 | C23—C21—H21 | 108.1 |
C11—C12—H12 | 119.6 | C22—C21—H21 | 108.1 |
C12—C13—C8 | 119.2 (14) | C21—C22—H22A | 109.5 |
C12—C13—H13 | 120.4 | C21—C22—H22B | 109.5 |
C8—C13—H13 | 120.4 | H22A—C22—H22B | 109.5 |
O2—C14—O3 | 125.0 (13) | C21—C22—H22C | 109.5 |
O2—C14—C11 | 119.0 (11) | H22A—C22—H22C | 109.5 |
O3—C14—C11 | 116.0 (15) | H22B—C22—H22C | 109.5 |
C16—C15—C17 | 112.0 (10) | C21—C23—H23A | 109.5 |
C16—C15—C2 | 111.1 (11) | C21—C23—H23B | 109.5 |
C17—C15—C2 | 110.8 (9) | H23A—C23—H23B | 109.5 |
C16—C15—H15 | 107.6 | C21—C23—H23C | 109.5 |
C17—C15—H15 | 107.6 | H23A—C23—H23C | 109.5 |
C2—C15—H15 | 107.6 | H23B—C23—H23C | 109.5 |
C15—C16—H16A | 109.5 | O1D—C7D—C22D | 116 (4) |
C15—C16—H16B | 109.5 | O1D—C7D—C8 | 109 (3) |
H16A—C16—H16B | 109.5 | C22D—C7D—C8 | 111 (3) |
C15—C16—H16C | 109.5 | O1D—C7D—C1 | 109 (4) |
H16A—C16—H16C | 109.5 | C22D—C7D—C1 | 99 (3) |
H16B—C16—H16C | 109.5 | C8—C7D—C1 | 113 (2) |
C15—C17—H17A | 109.5 | C23D—C21D—C22D | 120 (5) |
C15—C17—H17B | 109.5 | C23D—C21D—C6 | 116 (5) |
H17A—C17—H17B | 109.5 | C22D—C21D—C6 | 99 (3) |
C15—C17—H17C | 109.5 | C23D—C21D—H21D | 106.8 |
H17A—C17—H17C | 109.5 | C22D—C21D—H21D | 106.8 |
H17B—C17—H17C | 109.5 | C6—C21D—H21D | 106.8 |
C4—C18—C20 | 114.1 (17) | C7D—C22D—C21D | 109 (3) |
C4—C18—C19 | 115.9 (12) | C7D—C22D—H22D | 110.0 |
C20—C18—C19 | 111.2 (16) | C21D—C22D—H22D | 110.0 |
C4—C18—H18 | 104.7 | C7D—C22D—H22E | 110.0 |
C20—C18—H18 | 104.7 | C21D—C22D—H22E | 110.0 |
C19—C18—H18 | 104.7 | H22D—C22D—H22E | 108.3 |
C18—C19—H19A | 109.5 | C21D—C23D—H23E | 109.5 |
C18—C19—H19B | 109.5 | C21D—C23D—H23D | 109.5 |
H19A—C19—H19B | 109.5 | H23E—C23D—H23D | 109.5 |
C18—C19—H19C | 109.5 | C21D—C23D—H23F | 109.5 |
H19A—C19—H19C | 109.5 | H23E—C23D—H23F | 109.5 |
H19B—C19—H19C | 109.5 | H23D—C23D—H23F | 109.5 |
C31H39NO3 | Dx = 1.245 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 806 reflections |
a = 5.9717 (12) Å | θ = 5.6–21.7° |
b = 13.299 (5) Å | µ = 0.08 mm−1 |
c = 31.81 (3) Å | T = 299 K |
V = 2526 (3) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.10 × 0.08 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 1901 independent reflections |
Radiation source: fine-focus sealed tube | 778 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.100 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 24.7°, θmin = 5.6° |
φ– and ω scans | h = −6→6 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −11→14 |
Tmin = 0.272, Tmax = 1.000 | l = −20→22 |
4915 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.088 | w = 1/[σ2(Fo2) + (0.0814P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.247 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.15 e Å−3 |
1901 reflections | Δρmin = −0.16 e Å−3 |
192 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
65 restraints | Absolute structure parameter: 0.8 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O2 | 0.3842 (15) | 0.6234 (8) | 0.4827 (5) | 0.072 (6) | |
O3 | 0.6931 (16) | 0.6128 (8) | 0.4443 (6) | 0.094 (7) | |
N1 | 0.9553 (17) | 0.6719 (9) | 0.5106 (7) | 0.076 (9) | |
H1A | 0.9766 | 0.7377 | 0.5137 | 0.091* | |
H1B | 0.8381 | 0.6614 | 0.4939 | 0.091* | |
H1C | 1.0768 | 0.6443 | 0.4992 | 0.091* | |
C1 | 0.179 (2) | 0.2566 (11) | 0.3094 (7) | 0.057 (4)* | |
C2 | 0.097 (2) | 0.3181 (10) | 0.2784 (8) | 0.053 (4)* | |
C3 | 0.160 (2) | 0.3028 (11) | 0.2367 (8) | 0.058 (3)* | |
H3 | 0.1041 | 0.3462 | 0.2164 | 0.069* | |
C4 | 0.304 (2) | 0.2254 (11) | 0.2239 (9) | 0.062 (4)* | |
C5 | 0.380 (2) | 0.1675 (11) | 0.2594 (8) | 0.058 (3)* | |
H5 | 0.4816 | 0.1167 | 0.2530 | 0.069* | |
C6 | 0.327 (2) | 0.1755 (11) | 0.3002 (7) | 0.064 (5)* | |
C8 | 0.207 (2) | 0.3482 (12) | 0.3810 (8) | 0.065 (2)* | |
C9 | 0.100 (2) | 0.3833 (11) | 0.4163 (7) | 0.065 (2)* | |
H9 | −0.0356 | 0.3551 | 0.4245 | 0.078* | |
C10 | 0.192 (2) | 0.4595 (11) | 0.4395 (8) | 0.065 (2)* | |
H10 | 0.1170 | 0.4848 | 0.4628 | 0.078* | |
C11 | 0.400 (2) | 0.4989 (11) | 0.4281 (8) | 0.065 (2)* | |
C12 | 0.513 (2) | 0.4604 (12) | 0.3937 (8) | 0.065 (2)* | |
H12 | 0.6547 | 0.4847 | 0.3870 | 0.078* | |
C13 | 0.418 (2) | 0.3864 (12) | 0.3691 (7) | 0.065 (2)* | |
H13 | 0.4909 | 0.3624 | 0.3453 | 0.078* | |
C14 | 0.500 (3) | 0.5840 (13) | 0.4558 (9) | 0.065 (5)* | |
C15 | −0.055 (2) | 0.4064 (10) | 0.2910 (8) | 0.079 (10) | |
H15 | −0.0796 | 0.4009 | 0.3213 | 0.095* | |
C16 | −0.2818 (19) | 0.4024 (12) | 0.2705 (8) | 0.069 (5)* | |
H16A | −0.3494 | 0.3381 | 0.2759 | 0.104* | |
H16B | −0.3749 | 0.4546 | 0.2818 | 0.104* | |
H16C | −0.2659 | 0.4118 | 0.2407 | 0.104* | |
C17 | 0.060 (2) | 0.5057 (11) | 0.2836 (8) | 0.074 (5)* | |
H17A | 0.2035 | 0.5054 | 0.2971 | 0.111* | |
H17B | 0.0788 | 0.5160 | 0.2539 | 0.111* | |
H17C | −0.0301 | 0.5589 | 0.2950 | 0.111* | |
C18 | 0.368 (2) | 0.2043 (13) | 0.1814 (9) | 0.075 (5)* | |
H18 | 0.3550 | 0.1311 | 0.1786 | 0.090* | |
C19 | 0.213 (2) | 0.2478 (15) | 0.1465 (9) | 0.102 (7)* | |
H19A | 0.2706 | 0.2294 | 0.1194 | 0.153* | |
H19B | 0.0646 | 0.2212 | 0.1497 | 0.153* | |
H19C | 0.2084 | 0.3198 | 0.1488 | 0.153* | |
C20 | 0.613 (2) | 0.2277 (13) | 0.1721 (9) | 0.096 (6)* | |
H20A | 0.6458 | 0.2121 | 0.1433 | 0.143* | |
H20B | 0.6415 | 0.2978 | 0.1771 | 0.143* | |
H20C | 0.7073 | 0.1880 | 0.1902 | 0.143* | |
C24 | 0.687 (2) | 0.6678 (12) | 0.5689 (8) | 0.083 (6)* | |
H24A | 0.6943 | 0.7399 | 0.5688 | 0.125* | |
H24B | 0.5689 | 0.6458 | 0.5506 | 0.125* | |
H24C | 0.6590 | 0.6445 | 0.5969 | 0.125* | |
C25 | 0.911 (3) | 0.6247 (16) | 0.5533 (11) | 0.086 (6)* | |
H25 | 1.0278 | 0.6494 | 0.5724 | 0.103* | |
C26 | 0.936 (2) | 0.5121 (11) | 0.5510 (9) | 0.070 (5)* | |
C27 | 0.760 (2) | 0.4537 (14) | 0.5353 (9) | 0.082 (6)* | |
H27 | 0.6287 | 0.4835 | 0.5256 | 0.099* | |
C28 | 0.786 (2) | 0.3501 (14) | 0.5346 (9) | 0.080 (6)* | |
H28 | 0.6652 | 0.3098 | 0.5274 | 0.097* | |
C29 | 0.983 (3) | 0.3067 (15) | 0.5442 (9) | 0.095 (6)* | |
H29 | 0.9997 | 0.2372 | 0.5424 | 0.114* | |
C30 | 1.154 (3) | 0.3637 (15) | 0.5561 (10) | 0.097 (6)* | |
H30 | 1.2909 | 0.3330 | 0.5620 | 0.117* | |
C31 | 1.137 (2) | 0.4677 (13) | 0.5603 (9) | 0.083 (6)* | |
H31 | 1.2584 | 0.5060 | 0.5691 | 0.099* | |
O1 | −0.066 (3) | 0.2249 (13) | 0.3681 (7) | 0.103 (8) | 0.87 (2) |
C7 | 0.098 (3) | 0.2700 (15) | 0.3545 (7) | 0.083 (9) | 0.87 (2) |
C21 | 0.408 (2) | 0.1038 (15) | 0.3343 (8) | 0.070 (7) | 0.87 (2) |
H21 | 0.4369 | 0.1440 | 0.3595 | 0.083* | 0.87 (2) |
C22 | 0.230 (3) | 0.0275 (15) | 0.3456 (10) | 0.099 (8)* | 0.87 (2) |
H22A | 0.2862 | −0.0164 | 0.3671 | 0.148* | 0.87 (2) |
H22B | 0.0992 | 0.0617 | 0.3557 | 0.148* | 0.87 (2) |
H22C | 0.1921 | −0.0112 | 0.3211 | 0.148* | 0.87 (2) |
C23 | 0.626 (3) | 0.0507 (15) | 0.3227 (10) | 0.085 (8)* | 0.87 (2) |
H23A | 0.7371 | 0.0999 | 0.3156 | 0.127* | 0.87 (2) |
H23B | 0.6766 | 0.0115 | 0.3461 | 0.127* | 0.87 (2) |
H23C | 0.6005 | 0.0074 | 0.2990 | 0.127* | 0.87 (2) |
O1D | −0.134 (7) | 0.262 (7) | 0.359 (3) | 0.098 (18)* | 0.13 (2) |
C7D | 0.108 (7) | 0.258 (3) | 0.3570 (9) | 0.082 (17)* | 0.13 (2) |
C21D | 0.411 (13) | 0.134 (6) | 0.3424 (12) | 0.075 (17)* | 0.13 (2) |
H21D | 0.5324 | 0.1786 | 0.3513 | 0.090* | 0.13 (2) |
C22D | 0.212 (13) | 0.158 (4) | 0.3708 (19) | 0.082 (16)* | 0.13 (2) |
H22D | 0.1009 | 0.1053 | 0.3690 | 0.098* | 0.13 (2) |
H22E | 0.2611 | 0.1633 | 0.3998 | 0.098* | 0.13 (2) |
C23D | 0.51 (2) | 0.031 (6) | 0.341 (3) | 0.09 (3)* | 0.13 (2) |
H23E | 0.6311 | 0.0293 | 0.3218 | 0.133* | 0.13 (2) |
H23D | 0.5606 | 0.0129 | 0.3688 | 0.133* | 0.13 (2) |
H23F | 0.3956 | −0.0162 | 0.3324 | 0.133* | 0.13 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.067 (6) | 0.069 (9) | 0.08 (2) | −0.002 (5) | −0.004 (8) | −0.016 (7) |
O3 | 0.079 (6) | 0.092 (10) | 0.11 (2) | −0.027 (6) | 0.008 (9) | −0.005 (9) |
N1 | 0.054 (6) | 0.050 (10) | 0.12 (3) | −0.005 (6) | −0.023 (10) | −0.010 (9) |
C15 | 0.065 (7) | 0.033 (11) | 0.14 (4) | −0.013 (7) | −0.017 (11) | 0.000 (10) |
O1 | 0.108 (9) | 0.106 (13) | 0.09 (2) | −0.042 (10) | 0.031 (12) | −0.041 (11) |
C7 | 0.066 (10) | 0.098 (15) | 0.08 (3) | −0.005 (11) | 0.005 (14) | −0.026 (14) |
C21 | 0.064 (9) | 0.063 (12) | 0.081 (19) | −0.001 (9) | −0.015 (11) | 0.021 (11) |
O2—C14 | 1.22 (2) | C18—H18 | 0.9800 |
O3—C14 | 1.267 (18) | C19—H19A | 0.9600 |
N1—C25 | 1.52 (3) | C19—H19B | 0.9600 |
N1—H1A | 0.8900 | C19—H19C | 0.9600 |
N1—H1B | 0.8900 | C20—H20A | 0.9600 |
N1—H1C | 0.8900 | C20—H20B | 0.9600 |
C1—C2 | 1.37 (2) | C20—H20C | 0.9600 |
C1—C6 | 1.425 (19) | C24—C25 | 1.54 (2) |
C1—C7 | 1.53 (2) | C24—H24A | 0.9600 |
C1—C7D | 1.57 (2) | C24—H24B | 0.9600 |
C2—C3 | 1.39 (3) | C24—H24C | 0.9600 |
C2—C15 | 1.534 (19) | C25—C26 | 1.51 (2) |
C3—C4 | 1.40 (2) | C25—H25 | 0.9800 |
C3—H3 | 0.9300 | C26—C31 | 1.37 (2) |
C4—C18 | 1.43 (3) | C26—C27 | 1.40 (2) |
C4—C5 | 1.44 (3) | C27—C28 | 1.387 (19) |
C5—C6 | 1.34 (3) | C27—H27 | 0.9300 |
C5—H5 | 0.9300 | C28—C29 | 1.35 (2) |
C6—C21 | 1.521 (19) | C28—H28 | 0.9300 |
C6—C21D | 1.53 (3) | C29—C30 | 1.33 (2) |
C8—C9 | 1.37 (2) | C29—H29 | 0.9300 |
C8—C13 | 1.41 (2) | C30—C31 | 1.39 (2) |
C8—C7 | 1.486 (19) | C30—H30 | 0.9300 |
C8—C7D | 1.54 (2) | C31—H31 | 0.9300 |
C9—C10 | 1.37 (2) | O1—C7 | 1.227 (17) |
C9—H9 | 0.9300 | C21—C22 | 1.510 (18) |
C10—C11 | 1.397 (18) | C21—C23 | 1.527 (19) |
C10—H10 | 0.9300 | C21—H21 | 0.9800 |
C11—C12 | 1.38 (3) | C22—H22A | 0.9600 |
C11—C14 | 1.55 (3) | C22—H22B | 0.9600 |
C12—C13 | 1.38 (2) | C22—H22C | 0.9600 |
C12—H12 | 0.9300 | C23—H23A | 0.9600 |
C13—H13 | 0.9300 | C23—H23B | 0.9600 |
C15—C16 | 1.50 (2) | C23—H23C | 0.9600 |
C15—C17 | 1.505 (18) | O1D—C7D | 1.45 (3) |
C15—H15 | 0.9800 | C7D—C22D | 1.53 (3) |
C16—H16A | 0.9600 | C21D—C23D | 1.49 (3) |
C16—H16B | 0.9600 | C21D—C22D | 1.53 (3) |
C16—H16C | 0.9600 | C21D—H21D | 0.9800 |
C17—H17A | 0.9600 | C22D—H22D | 0.9700 |
C17—H17B | 0.9600 | C22D—H22E | 0.9700 |
C17—H17C | 0.9600 | C23D—H23E | 0.9600 |
C18—C20 | 1.53 (2) | C23D—H23D | 0.9600 |
C18—C19 | 1.56 (3) | C23D—H23F | 0.9600 |
C25—N1—H1A | 109.5 | C18—C20—H20A | 109.5 |
C25—N1—H1B | 109.5 | C18—C20—H20B | 109.5 |
H1A—N1—H1B | 109.5 | H20A—C20—H20B | 109.5 |
C25—N1—H1C | 109.5 | C18—C20—H20C | 109.5 |
H1A—N1—H1C | 109.5 | H20A—C20—H20C | 109.5 |
H1B—N1—H1C | 109.5 | H20B—C20—H20C | 109.5 |
C2—C1—C6 | 121.8 (18) | C25—C24—H24A | 109.5 |
C2—C1—C7 | 119.5 (15) | C25—C24—H24B | 109.5 |
C6—C1—C7 | 118.5 (16) | H24A—C24—H24B | 109.5 |
C2—C1—C7D | 126 (2) | C25—C24—H24C | 109.5 |
C6—C1—C7D | 112 (2) | H24A—C24—H24C | 109.5 |
C1—C2—C3 | 119.9 (16) | H24B—C24—H24C | 109.5 |
C1—C2—C15 | 118.8 (19) | C26—C25—N1 | 111 (2) |
C3—C2—C15 | 121.3 (17) | C26—C25—C24 | 118.1 (15) |
C2—C3—C4 | 123 (2) | N1—C25—C24 | 106.5 (17) |
C2—C3—H3 | 118.3 | C26—C25—H25 | 107.0 |
C4—C3—H3 | 118.3 | N1—C25—H25 | 107.0 |
C3—C4—C18 | 126 (2) | C24—C25—H25 | 107.0 |
C3—C4—C5 | 111 (2) | C31—C26—C27 | 119.8 (16) |
C18—C4—C5 | 123.4 (16) | C31—C26—C25 | 120.3 (16) |
C6—C5—C4 | 130.0 (18) | C27—C26—C25 | 119.6 (16) |
C6—C5—H5 | 115.0 | C28—C27—C26 | 118.0 (16) |
C4—C5—H5 | 115.0 | C28—C27—H27 | 121.0 |
C5—C6—C1 | 113.8 (16) | C26—C27—H27 | 121.0 |
C5—C6—C21 | 124.4 (17) | C29—C28—C27 | 121.6 (17) |
C1—C6—C21 | 121.7 (19) | C29—C28—H28 | 119.2 |
C5—C6—C21D | 138 (2) | C27—C28—H28 | 119.2 |
C1—C6—C21D | 107 (2) | C30—C29—C28 | 119.4 (19) |
C9—C8—C13 | 120.7 (16) | C30—C29—H29 | 120.3 |
C9—C8—C7 | 119.8 (13) | C28—C29—H29 | 120.3 |
C13—C8—C7 | 119.4 (18) | C29—C30—C31 | 122.4 (19) |
C9—C8—C7D | 119.5 (17) | C29—C30—H30 | 118.8 |
C13—C8—C7D | 119 (2) | C31—C30—H30 | 118.8 |
C10—C9—C8 | 120.4 (14) | C26—C31—C30 | 118.3 (17) |
C10—C9—H9 | 119.8 | C26—C31—H31 | 120.9 |
C8—C9—H9 | 119.8 | C30—C31—H31 | 120.9 |
C9—C10—C11 | 119.7 (19) | O1—C7—C8 | 119.5 (18) |
C9—C10—H10 | 120.2 | O1—C7—C1 | 121.7 (16) |
C11—C10—H10 | 120.2 | C8—C7—C1 | 118.4 (15) |
C12—C11—C10 | 119.9 (17) | C22—C21—C6 | 111.6 (15) |
C12—C11—C14 | 122.2 (14) | C22—C21—C23 | 110.2 (16) |
C10—C11—C14 | 118 (2) | C6—C21—C23 | 112.8 (18) |
C13—C12—C11 | 120.9 (14) | C22—C21—H21 | 107.3 |
C13—C12—H12 | 119.6 | C6—C21—H21 | 107.3 |
C11—C12—H12 | 119.6 | C23—C21—H21 | 107.3 |
C12—C13—C8 | 118.2 (19) | C21—C22—H22A | 109.5 |
C12—C13—H13 | 120.9 | C21—C22—H22B | 109.5 |
C8—C13—H13 | 120.9 | H22A—C22—H22B | 109.5 |
O2—C14—O3 | 126.1 (19) | C21—C22—H22C | 109.5 |
O2—C14—C11 | 119.6 (14) | H22A—C22—H22C | 109.5 |
O3—C14—C11 | 114 (2) | H22B—C22—H22C | 109.5 |
C16—C15—C17 | 111.9 (14) | C21—C23—H23A | 109.5 |
C16—C15—C2 | 113.0 (14) | C21—C23—H23B | 109.5 |
C17—C15—C2 | 111.3 (11) | H23A—C23—H23B | 109.5 |
C16—C15—H15 | 106.7 | C21—C23—H23C | 109.5 |
C17—C15—H15 | 106.7 | H23A—C23—H23C | 109.5 |
C2—C15—H15 | 106.7 | H23B—C23—H23C | 109.5 |
C15—C16—H16A | 109.5 | O1D—C7D—C22D | 115 (4) |
C15—C16—H16B | 109.5 | O1D—C7D—C8 | 109 (3) |
H16A—C16—H16B | 109.5 | C22D—C7D—C8 | 112 (3) |
C15—C16—H16C | 109.5 | O1D—C7D—C1 | 108 (3) |
H16A—C16—H16C | 109.5 | C22D—C7D—C1 | 99 (3) |
H16B—C16—H16C | 109.5 | C8—C7D—C1 | 113 (2) |
C15—C17—H17A | 109.5 | C23D—C21D—C22D | 121 (5) |
C15—C17—H17B | 109.5 | C23D—C21D—C6 | 116 (4) |
H17A—C17—H17B | 109.5 | C22D—C21D—C6 | 101 (3) |
C15—C17—H17C | 109.5 | C23D—C21D—H21D | 106.0 |
H17A—C17—H17C | 109.5 | C22D—C21D—H21D | 106.0 |
H17B—C17—H17C | 109.5 | C6—C21D—H21D | 106.0 |
C4—C18—C20 | 113 (2) | C7D—C22D—C21D | 109 (3) |
C4—C18—C19 | 116.3 (15) | C7D—C22D—H22D | 109.8 |
C20—C18—C19 | 111 (2) | C21D—C22D—H22D | 109.8 |
C4—C18—H18 | 105.0 | C7D—C22D—H22E | 109.8 |
C20—C18—H18 | 105.0 | C21D—C22D—H22E | 109.8 |
C19—C18—H18 | 105.0 | H22D—C22D—H22E | 108.3 |
C18—C19—H19A | 109.5 | C21D—C23D—H23E | 109.5 |
C18—C19—H19B | 109.5 | C21D—C23D—H23D | 109.5 |
H19A—C19—H19B | 109.5 | H23E—C23D—H23D | 109.5 |
C18—C19—H19C | 109.5 | C21D—C23D—H23F | 109.5 |
H19A—C19—H19C | 109.5 | H23E—C23D—H23F | 109.5 |
H19B—C19—H19C | 109.5 | H23D—C23D—H23F | 109.5 |
C31H39NO3 | Dx = 1.244 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 822 reflections |
a = 5.9814 (12) Å | θ = 5.6–23.4° |
b = 13.288 (5) Å | µ = 0.08 mm−1 |
c = 31.81 (3) Å | T = 299 K |
V = 2528 (3) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.10 × 0.08 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 1913 independent reflections |
Radiation source: fine-focus sealed tube | 843 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.099 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 24.7°, θmin = 5.6° |
φ– and ω scans | h = −6→6 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −11→14 |
Tmin = 0.244, Tmax = 1.000 | l = −20→22 |
4926 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.084 | w = 1/[σ2(Fo2) + (0.0394P)2 + 2.360P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.182 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.18 e Å−3 |
1913 reflections | Δρmin = −0.14 e Å−3 |
193 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
65 restraints | Absolute structure parameter: 4.1 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O2 | 0.3819 (14) | 0.6228 (6) | 0.4827 (4) | 0.063 (5) | |
O3 | 0.6909 (15) | 0.6124 (8) | 0.4445 (5) | 0.087 (6) | |
N1 | 0.9551 (15) | 0.6714 (7) | 0.5106 (6) | 0.066 (7) | |
H1A | 0.9665 | 0.7377 | 0.5139 | 0.080* | |
H1B | 0.8420 | 0.6576 | 0.4933 | 0.080* | |
H1C | 1.0816 | 0.6475 | 0.4998 | 0.080* | |
C1 | 0.1794 (19) | 0.2577 (9) | 0.3089 (6) | 0.049 (4)* | |
C2 | 0.0951 (19) | 0.3205 (9) | 0.2787 (7) | 0.048 (4)* | |
C3 | 0.1597 (18) | 0.3039 (9) | 0.2374 (7) | 0.047 (4)* | |
H3 | 0.1026 | 0.3464 | 0.2168 | 0.056* | |
C4 | 0.3049 (19) | 0.2275 (10) | 0.2249 (7) | 0.051 (4)* | |
C5 | 0.3838 (18) | 0.1652 (9) | 0.2584 (7) | 0.045 (4)* | |
H5 | 0.4803 | 0.1128 | 0.2516 | 0.054* | |
C6 | 0.327 (2) | 0.1772 (10) | 0.3002 (7) | 0.053 (4)* | |
C8 | 0.206 (2) | 0.3486 (10) | 0.3805 (7) | 0.0576 (19)* | |
C9 | 0.097 (2) | 0.3840 (10) | 0.4164 (6) | 0.0576 (19)* | |
H9 | −0.0380 | 0.3557 | 0.4246 | 0.069* | |
C10 | 0.190 (2) | 0.4608 (9) | 0.4398 (7) | 0.0576 (19)* | |
H10 | 0.1150 | 0.4868 | 0.4629 | 0.069* | |
C11 | 0.399 (2) | 0.4991 (10) | 0.4282 (7) | 0.0576 (19)* | |
C12 | 0.511 (2) | 0.4614 (10) | 0.3935 (7) | 0.0576 (19)* | |
H12 | 0.6510 | 0.4865 | 0.3866 | 0.069* | |
C13 | 0.417 (2) | 0.3873 (10) | 0.3691 (6) | 0.0576 (19)* | |
H13 | 0.4909 | 0.3632 | 0.3455 | 0.069* | |
C14 | 0.498 (3) | 0.5848 (12) | 0.4551 (8) | 0.058 (5)* | |
C15 | −0.0540 (19) | 0.4075 (9) | 0.2910 (7) | 0.061 (8) | |
H15 | −0.0807 | 0.4012 | 0.3213 | 0.074* | |
C16 | −0.2796 (17) | 0.4027 (10) | 0.2700 (7) | 0.060 (4)* | |
H16A | −0.3458 | 0.3380 | 0.2751 | 0.090* | |
H16B | −0.3745 | 0.4543 | 0.2813 | 0.090* | |
H16C | −0.2622 | 0.4126 | 0.2403 | 0.090* | |
C17 | 0.061 (2) | 0.5076 (9) | 0.2844 (7) | 0.066 (5)* | |
H17A | 0.2035 | 0.5070 | 0.2983 | 0.100* | |
H17B | 0.0825 | 0.5188 | 0.2549 | 0.100* | |
H17C | −0.0298 | 0.5605 | 0.2959 | 0.100* | |
C18 | 0.368 (2) | 0.2015 (12) | 0.1814 (8) | 0.071 (5)* | |
H18 | 0.3562 | 0.1281 | 0.1790 | 0.085* | |
C19 | 0.215 (2) | 0.2464 (13) | 0.1466 (9) | 0.103 (7)* | |
H19A | 0.2687 | 0.2256 | 0.1195 | 0.155* | |
H19B | 0.0649 | 0.2230 | 0.1505 | 0.155* | |
H19C | 0.2181 | 0.3186 | 0.1483 | 0.155* | |
C20 | 0.615 (2) | 0.2287 (11) | 0.1731 (8) | 0.085 (5)* | |
H20A | 0.6531 | 0.2114 | 0.1447 | 0.127* | |
H20B | 0.6359 | 0.2996 | 0.1773 | 0.127* | |
H20C | 0.7084 | 0.1920 | 0.1922 | 0.127* | |
C24 | 0.6908 (19) | 0.6669 (10) | 0.5687 (7) | 0.075 (5)* | |
H24A | 0.7008 | 0.7390 | 0.5692 | 0.112* | |
H24B | 0.5718 | 0.6469 | 0.5503 | 0.112* | |
H24C | 0.6613 | 0.6425 | 0.5966 | 0.112* | |
C25 | 0.913 (2) | 0.6226 (13) | 0.5528 (9) | 0.074 (5)* | |
H25 | 1.0308 | 0.6457 | 0.5719 | 0.089* | |
C26 | 0.932 (2) | 0.5136 (10) | 0.5497 (7) | 0.061 (4)* | |
C27 | 0.759 (2) | 0.4538 (11) | 0.5352 (8) | 0.066 (5)* | |
H27 | 0.6257 | 0.4830 | 0.5265 | 0.079* | |
C28 | 0.786 (2) | 0.3501 (12) | 0.5338 (8) | 0.079 (5)* | |
H28 | 0.6661 | 0.3098 | 0.5259 | 0.095* | |
C29 | 0.986 (3) | 0.3061 (13) | 0.5438 (8) | 0.092 (6)* | |
H29 | 1.0036 | 0.2368 | 0.5415 | 0.110* | |
C30 | 1.157 (3) | 0.3645 (13) | 0.5570 (8) | 0.090 (6)* | |
H30 | 1.2923 | 0.3348 | 0.5641 | 0.107* | |
C31 | 1.134 (2) | 0.4689 (12) | 0.5601 (8) | 0.076 (5)* | |
H31 | 1.2529 | 0.5081 | 0.5692 | 0.091* | |
O1 | −0.068 (3) | 0.2251 (11) | 0.3676 (6) | 0.091 (7) | 0.842 (19) |
C7 | 0.095 (3) | 0.2704 (14) | 0.3541 (7) | 0.072 (8) | 0.842 (19) |
C21 | 0.407 (3) | 0.1055 (13) | 0.3341 (7) | 0.062 (6) | 0.842 (19) |
H21 | 0.4318 | 0.1451 | 0.3597 | 0.074* | 0.842 (19) |
C22 | 0.225 (3) | 0.0277 (14) | 0.3440 (10) | 0.103 (9)* | 0.842 (19) |
H22A | 0.2769 | −0.0172 | 0.3655 | 0.155* | 0.842 (19) |
H22B | 0.0925 | 0.0617 | 0.3537 | 0.155* | 0.842 (19) |
H22C | 0.1904 | −0.0100 | 0.3191 | 0.155* | 0.842 (19) |
C23 | 0.624 (3) | 0.0511 (12) | 0.3240 (8) | 0.072 (7)* | 0.842 (19) |
H23A | 0.6624 | 0.0074 | 0.3469 | 0.108* | 0.842 (19) |
H23B | 0.6047 | 0.0120 | 0.2989 | 0.108* | 0.842 (19) |
H23C | 0.7407 | 0.0995 | 0.3198 | 0.108* | 0.842 (19) |
O1D | −0.129 (6) | 0.263 (6) | 0.359 (2) | 0.095 (18)* | 0.158 (19) |
C7D | 0.112 (7) | 0.257 (2) | 0.3568 (9) | 0.074 (16)* | 0.158 (19) |
C21D | 0.409 (11) | 0.129 (5) | 0.3410 (12) | 0.064 (16)* | 0.158 (19) |
H21D | 0.5408 | 0.1667 | 0.3505 | 0.077* | 0.158 (19) |
C22D | 0.215 (11) | 0.157 (3) | 0.3699 (17) | 0.072 (15)* | 0.158 (19) |
H22D | 0.1017 | 0.1044 | 0.3687 | 0.086* | 0.158 (19) |
H22E | 0.2677 | 0.1612 | 0.3987 | 0.086* | 0.158 (19) |
C23D | 0.480 (16) | 0.021 (5) | 0.335 (3) | 0.09 (3)* | 0.158 (19) |
H23D | 0.6037 | 0.0179 | 0.3163 | 0.128* | 0.158 (19) |
H23E | 0.5234 | −0.0064 | 0.3621 | 0.128* | 0.158 (19) |
H23F | 0.3570 | −0.0171 | 0.3243 | 0.128* | 0.158 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.061 (5) | 0.059 (7) | 0.069 (18) | 0.011 (5) | −0.003 (7) | −0.012 (6) |
O3 | 0.071 (6) | 0.090 (9) | 0.10 (2) | −0.026 (6) | 0.015 (8) | −0.014 (8) |
N1 | 0.052 (6) | 0.035 (8) | 0.11 (3) | 0.000 (5) | −0.020 (9) | −0.010 (8) |
C15 | 0.063 (7) | 0.037 (10) | 0.08 (3) | −0.009 (7) | −0.022 (11) | −0.002 (9) |
O1 | 0.107 (10) | 0.089 (12) | 0.08 (2) | −0.044 (10) | 0.037 (11) | −0.036 (10) |
C7 | 0.066 (11) | 0.085 (14) | 0.06 (2) | −0.008 (11) | 0.001 (14) | −0.011 (13) |
C21 | 0.066 (9) | 0.053 (12) | 0.066 (18) | −0.004 (9) | −0.001 (11) | −0.003 (10) |
O2—C14 | 1.23 (2) | C18—H18 | 0.9800 |
O3—C14 | 1.255 (16) | C19—H19A | 0.9600 |
N1—C25 | 1.51 (3) | C19—H19B | 0.9600 |
N1—H1A | 0.8900 | C19—H19C | 0.9600 |
N1—H1B | 0.8900 | C20—H20A | 0.9600 |
N1—H1C | 0.8900 | C20—H20B | 0.9600 |
C1—C2 | 1.37 (2) | C20—H20C | 0.9600 |
C1—C6 | 1.415 (17) | C24—C25 | 1.539 (19) |
C1—C7 | 1.531 (19) | C24—H24A | 0.9600 |
C1—C7D | 1.57 (2) | C24—H24B | 0.9600 |
C2—C3 | 1.38 (2) | C24—H24C | 0.9600 |
C2—C15 | 1.513 (17) | C25—C26 | 1.457 (19) |
C3—C4 | 1.395 (16) | C25—H25 | 0.9800 |
C3—H3 | 0.9300 | C26—C27 | 1.382 (18) |
C4—C5 | 1.43 (2) | C26—C31 | 1.384 (19) |
C4—C18 | 1.48 (3) | C27—C28 | 1.388 (16) |
C5—C6 | 1.38 (2) | C27—H27 | 0.9300 |
C5—H5 | 0.9300 | C28—C29 | 1.367 (18) |
C6—C21 | 1.516 (19) | C28—H28 | 0.9300 |
C6—C21D | 1.53 (3) | C29—C30 | 1.35 (2) |
C8—C9 | 1.40 (2) | C29—H29 | 0.9300 |
C8—C13 | 1.407 (18) | C30—C31 | 1.397 (17) |
C8—C7 | 1.494 (18) | C30—H30 | 0.9300 |
C8—C7D | 1.54 (2) | C31—H31 | 0.9300 |
C9—C10 | 1.378 (18) | O1—C7 | 1.223 (16) |
C9—H9 | 0.9300 | C21—C23 | 1.520 (17) |
C10—C11 | 1.400 (17) | C21—C22 | 1.534 (18) |
C10—H10 | 0.9300 | C21—H21 | 0.9800 |
C11—C12 | 1.38 (2) | C22—H22A | 0.9600 |
C11—C14 | 1.54 (2) | C22—H22B | 0.9600 |
C12—C13 | 1.37 (2) | C22—H22C | 0.9600 |
C12—H12 | 0.9300 | C23—H23A | 0.9600 |
C13—H13 | 0.9300 | C23—H23B | 0.9600 |
C15—C16 | 1.507 (17) | C23—H23C | 0.9600 |
C15—C17 | 1.511 (16) | O1D—C7D | 1.45 (3) |
C15—H15 | 0.9800 | C7D—C22D | 1.53 (3) |
C16—H16A | 0.9600 | C21D—C23D | 1.50 (3) |
C16—H16B | 0.9600 | C21D—C22D | 1.53 (3) |
C16—H16C | 0.9600 | C21D—H21D | 0.9800 |
C17—H17A | 0.9600 | C22D—H22D | 0.9700 |
C17—H17B | 0.9600 | C22D—H22E | 0.9700 |
C17—H17C | 0.9600 | C23D—H23D | 0.9600 |
C18—C20 | 1.543 (17) | C23D—H23E | 0.9600 |
C18—C19 | 1.55 (3) | C23D—H23F | 0.9600 |
C25—N1—H1A | 109.5 | C18—C20—H20A | 109.5 |
C25—N1—H1B | 109.5 | C18—C20—H20B | 109.5 |
H1A—N1—H1B | 109.5 | H20A—C20—H20B | 109.5 |
C25—N1—H1C | 109.5 | C18—C20—H20C | 109.5 |
H1A—N1—H1C | 109.5 | H20A—C20—H20C | 109.5 |
H1B—N1—H1C | 109.5 | H20B—C20—H20C | 109.5 |
C2—C1—C6 | 123.5 (17) | C25—C24—H24A | 109.5 |
C2—C1—C7 | 118.1 (14) | C25—C24—H24B | 109.5 |
C6—C1—C7 | 118.2 (14) | H24A—C24—H24B | 109.5 |
C2—C1—C7D | 126.2 (19) | C25—C24—H24C | 109.5 |
C6—C1—C7D | 110.1 (19) | H24A—C24—H24C | 109.5 |
C1—C2—C3 | 117.8 (14) | H24B—C24—H24C | 109.5 |
C1—C2—C15 | 120.0 (18) | C26—C25—N1 | 110.6 (19) |
C3—C2—C15 | 122.2 (15) | C26—C25—C24 | 118.1 (13) |
C2—C3—C4 | 124.1 (17) | N1—C25—C24 | 105.8 (14) |
C2—C3—H3 | 117.9 | C26—C25—H25 | 107.3 |
C4—C3—H3 | 117.9 | N1—C25—H25 | 107.3 |
C3—C4—C5 | 114 (2) | C24—C25—H25 | 107.3 |
C3—C4—C18 | 126.7 (18) | C27—C26—C31 | 119.0 (14) |
C5—C4—C18 | 118.7 (14) | C27—C26—C25 | 122.4 (14) |
C6—C5—C4 | 124.8 (15) | C31—C26—C25 | 118.6 (14) |
C6—C5—H5 | 117.6 | C26—C27—C28 | 119.6 (14) |
C4—C5—H5 | 117.6 | C26—C27—H27 | 120.2 |
C5—C6—C1 | 115.4 (14) | C28—C27—H27 | 120.2 |
C5—C6—C21 | 122.4 (15) | C29—C28—C27 | 121.2 (15) |
C1—C6—C21 | 122.1 (18) | C29—C28—H28 | 119.4 |
C5—C6—C21D | 133.6 (19) | C27—C28—H28 | 119.4 |
C1—C6—C21D | 111 (2) | C30—C29—C28 | 119.2 (16) |
C9—C8—C13 | 120.3 (15) | C30—C29—H29 | 120.4 |
C9—C8—C7 | 119.2 (12) | C28—C29—H29 | 120.4 |
C13—C8—C7 | 120.5 (16) | C29—C30—C31 | 121.2 (16) |
C9—C8—C7D | 119.8 (16) | C29—C30—H30 | 119.4 |
C13—C8—C7D | 119.3 (19) | C31—C30—H30 | 119.4 |
C10—C9—C8 | 120.1 (13) | C26—C31—C30 | 119.7 (16) |
C10—C9—H9 | 120.0 | C26—C31—H31 | 120.2 |
C8—C9—H9 | 120.0 | C30—C31—H31 | 120.2 |
C9—C10—C11 | 119.2 (17) | O1—C7—C8 | 119.9 (17) |
C9—C10—H10 | 120.4 | O1—C7—C1 | 122.6 (15) |
C11—C10—H10 | 120.4 | C8—C7—C1 | 117.3 (14) |
C12—C11—C10 | 120.6 (16) | C6—C21—C23 | 114.6 (17) |
C12—C11—C14 | 121.8 (14) | C6—C21—C22 | 110.3 (15) |
C10—C11—C14 | 117.7 (18) | C23—C21—C22 | 109.2 (14) |
C13—C12—C11 | 120.9 (13) | C6—C21—H21 | 107.5 |
C13—C12—H12 | 119.5 | C23—C21—H21 | 107.5 |
C11—C12—H12 | 119.5 | C22—C21—H21 | 107.5 |
C12—C13—C8 | 118.8 (17) | C21—C22—H22A | 109.5 |
C12—C13—H13 | 120.6 | C21—C22—H22B | 109.5 |
C8—C13—H13 | 120.6 | H22A—C22—H22B | 109.5 |
O2—C14—O3 | 126.3 (17) | C21—C22—H22C | 109.5 |
O2—C14—C11 | 118.9 (13) | H22A—C22—H22C | 109.5 |
O3—C14—C11 | 114.7 (19) | H22B—C22—H22C | 109.5 |
C16—C15—C17 | 112.5 (12) | C21—C23—H23A | 109.5 |
C16—C15—C2 | 112.3 (12) | C21—C23—H23B | 109.5 |
C17—C15—C2 | 111.6 (10) | H23A—C23—H23B | 109.5 |
C16—C15—H15 | 106.6 | C21—C23—H23C | 109.5 |
C17—C15—H15 | 106.6 | H23A—C23—H23C | 109.5 |
C2—C15—H15 | 106.6 | H23B—C23—H23C | 109.5 |
C15—C16—H16A | 109.5 | O1D—C7D—C22D | 116 (3) |
C15—C16—H16B | 109.5 | O1D—C7D—C8 | 107 (3) |
H16A—C16—H16B | 109.5 | C22D—C7D—C8 | 114 (3) |
C15—C16—H16C | 109.5 | O1D—C7D—C1 | 107 (3) |
H16A—C16—H16C | 109.5 | C22D—C7D—C1 | 100 (3) |
H16B—C16—H16C | 109.5 | C8—C7D—C1 | 112 (2) |
C15—C17—H17A | 109.5 | C23D—C21D—C22D | 121 (5) |
C15—C17—H17B | 109.5 | C23D—C21D—C6 | 113 (4) |
H17A—C17—H17B | 109.5 | C22D—C21D—C6 | 99 (3) |
C15—C17—H17C | 109.5 | C23D—C21D—H21D | 107.6 |
H17A—C17—H17C | 109.5 | C22D—C21D—H21D | 107.6 |
H17B—C17—H17C | 109.5 | C6—C21D—H21D | 107.6 |
C4—C18—C20 | 110.3 (16) | C7D—C22D—C21D | 111 (3) |
C4—C18—C19 | 115.4 (14) | C7D—C22D—H22D | 109.5 |
C20—C18—C19 | 110.6 (17) | C21D—C22D—H22D | 109.5 |
C4—C18—H18 | 106.7 | C7D—C22D—H22E | 109.5 |
C20—C18—H18 | 106.7 | C21D—C22D—H22E | 109.5 |
C19—C18—H18 | 106.7 | H22D—C22D—H22E | 108.1 |
C18—C19—H19A | 109.5 | C21D—C23D—H23D | 109.5 |
C18—C19—H19B | 109.5 | C21D—C23D—H23E | 109.5 |
H19A—C19—H19B | 109.5 | H23D—C23D—H23E | 109.5 |
C18—C19—H19C | 109.5 | C21D—C23D—H23F | 109.5 |
H19A—C19—H19C | 109.5 | H23D—C23D—H23F | 109.5 |
H19B—C19—H19C | 109.5 | H23E—C23D—H23F | 109.5 |
C31H39NO3 | Dx = 1.242 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 1102 reflections |
a = 5.9850 (11) Å | θ = 5.6–23.4° |
b = 13.301 (4) Å | µ = 0.08 mm−1 |
c = 31.82 (3) Å | T = 299 K |
V = 2533 (3) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.10 × 0.08 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 2240 independent reflections |
Radiation source: fine-focus sealed tube | 931 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.111 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 24.5°, θmin = 5.6° |
φ– and ω scans | h = −6→6 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −11→14 |
Tmin = 0.256, Tmax = 1.000 | l = −20→22 |
7190 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.087 | w = 1/[σ2(Fo2) + (0.0668P)2 + 2.3251P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.234 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.17 e Å−3 |
2240 reflections | Δρmin = −0.15 e Å−3 |
233 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
80 restraints | Absolute structure parameter: 2.7 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O2 | 0.3821 (15) | 0.6236 (7) | 0.4825 (5) | 0.078 (5) | |
O3 | 0.6913 (17) | 0.6135 (8) | 0.4448 (5) | 0.095 (6) | |
N1 | 0.9558 (17) | 0.6702 (7) | 0.5101 (6) | 0.076 (7) | |
H1A | 0.9474 | 0.7370 | 0.5114 | 0.091* | |
H1B | 0.8533 | 0.6473 | 0.4922 | 0.091* | |
H1C | 1.0911 | 0.6523 | 0.5012 | 0.091* | |
C1 | 0.175 (2) | 0.2573 (11) | 0.3084 (7) | 0.075 (5)* | |
C2 | 0.097 (2) | 0.3214 (10) | 0.2774 (7) | 0.059 (4)* | |
C3 | 0.162 (2) | 0.3039 (9) | 0.2372 (8) | 0.063 (4)* | |
H3 | 0.1062 | 0.3465 | 0.2165 | 0.076* | |
C4 | 0.307 (2) | 0.2259 (10) | 0.2243 (9) | 0.062 (5)* | |
C5 | 0.384 (2) | 0.1660 (10) | 0.2586 (7) | 0.059 (4)* | |
H5 | 0.4846 | 0.1149 | 0.2522 | 0.071* | |
C6 | 0.326 (2) | 0.1757 (10) | 0.2993 (7) | 0.061 (4)* | |
C8 | 0.204 (2) | 0.3473 (10) | 0.3801 (7) | 0.062 (4)* | |
C9 | 0.098 (3) | 0.3836 (10) | 0.4156 (7) | 0.072 (5)* | |
H9 | −0.0388 | 0.3561 | 0.4236 | 0.087* | |
C10 | 0.191 (2) | 0.4602 (9) | 0.4397 (7) | 0.067 (4)* | |
H10 | 0.1161 | 0.4846 | 0.4632 | 0.080* | |
C11 | 0.395 (2) | 0.4996 (9) | 0.4282 (8) | 0.065 (4)* | |
C12 | 0.512 (2) | 0.4632 (10) | 0.3943 (8) | 0.070 (5)* | |
H12 | 0.6526 | 0.4885 | 0.3878 | 0.084* | |
C13 | 0.416 (2) | 0.3872 (10) | 0.3697 (7) | 0.074 (5)* | |
H13 | 0.4915 | 0.3630 | 0.3463 | 0.089* | |
C14 | 0.499 (3) | 0.5845 (12) | 0.4544 (8) | 0.066 (5)* | |
C15 | −0.054 (2) | 0.4078 (9) | 0.2913 (8) | 0.085 (10) | |
H15 | −0.0780 | 0.4009 | 0.3217 | 0.101* | |
C16 | −0.278 (2) | 0.4030 (10) | 0.2707 (7) | 0.070 (8) | |
H16A | −0.3683 | 0.4582 | 0.2802 | 0.104* | |
H16B | −0.2601 | 0.4069 | 0.2408 | 0.104* | |
H16C | −0.3499 | 0.3408 | 0.2779 | 0.104* | |
C17 | 0.065 (2) | 0.5091 (9) | 0.2838 (8) | 0.091 (9) | |
H17A | 0.2075 | 0.5086 | 0.2976 | 0.136* | |
H17B | 0.0862 | 0.5190 | 0.2542 | 0.136* | |
H17C | −0.0246 | 0.5628 | 0.2949 | 0.136* | |
C18 | 0.370 (3) | 0.2031 (12) | 0.1802 (9) | 0.067 (8) | |
H18 | 0.3574 | 0.1299 | 0.1775 | 0.080* | |
C19 | 0.216 (3) | 0.2474 (14) | 0.1458 (9) | 0.096 (11) | |
H19A | 0.2705 | 0.2283 | 0.1186 | 0.144* | |
H19B | 0.0667 | 0.2219 | 0.1494 | 0.144* | |
H19C | 0.2138 | 0.3193 | 0.1480 | 0.144* | |
C20 | 0.616 (2) | 0.2278 (13) | 0.1717 (9) | 0.110 (11) | |
H20A | 0.6518 | 0.2122 | 0.1430 | 0.165* | |
H20B | 0.6422 | 0.2980 | 0.1768 | 0.165* | |
H20C | 0.7092 | 0.1886 | 0.1901 | 0.165* | |
C24 | 0.692 (2) | 0.6668 (10) | 0.5699 (8) | 0.090 (5)* | |
H24A | 0.6997 | 0.7388 | 0.5715 | 0.135* | |
H24B | 0.5741 | 0.6476 | 0.5510 | 0.135* | |
H24C | 0.6615 | 0.6401 | 0.5974 | 0.135* | |
C25 | 0.914 (3) | 0.6254 (12) | 0.5539 (9) | 0.086 (5)* | |
H25 | 1.0323 | 0.6486 | 0.5728 | 0.103* | |
C26 | 0.933 (2) | 0.5134 (10) | 0.5494 (8) | 0.072 (5)* | |
C27 | 0.762 (2) | 0.4537 (11) | 0.5349 (8) | 0.080 (5)* | |
H27 | 0.6279 | 0.4829 | 0.5264 | 0.096* | |
C28 | 0.788 (3) | 0.3497 (13) | 0.5330 (9) | 0.095 (6)* | |
H28 | 0.6692 | 0.3091 | 0.5246 | 0.114* | |
C29 | 0.986 (3) | 0.3081 (13) | 0.5435 (8) | 0.098 (6)* | |
H29 | 1.0041 | 0.2389 | 0.5414 | 0.118* | |
C30 | 1.157 (3) | 0.3641 (13) | 0.5567 (9) | 0.105 (6)* | |
H30 | 1.2916 | 0.3339 | 0.5638 | 0.126* | |
C31 | 1.133 (3) | 0.4675 (12) | 0.5599 (9) | 0.093 (6)* | |
H31 | 1.2522 | 0.5063 | 0.5691 | 0.111* | |
O1 | −0.069 (3) | 0.2256 (12) | 0.3677 (6) | 0.088 (7) | 0.81 (2) |
C7 | 0.097 (3) | 0.2687 (15) | 0.3538 (7) | 0.090 (8) | 0.81 (2) |
C21 | 0.406 (3) | 0.1050 (15) | 0.3344 (8) | 0.074 (7) | 0.81 (2) |
H21 | 0.4337 | 0.1448 | 0.3598 | 0.088* | 0.81 (2) |
C22 | 0.223 (3) | 0.0273 (15) | 0.3440 (10) | 0.103 (10) | 0.81 (2) |
H22A | 0.0878 | 0.0614 | 0.3517 | 0.155* | 0.81 (2) |
H22B | 0.1972 | −0.0133 | 0.3196 | 0.155* | 0.81 (2) |
H22C | 0.2706 | −0.0148 | 0.3668 | 0.155* | 0.81 (2) |
C23 | 0.621 (3) | 0.0501 (14) | 0.3223 (10) | 0.097 (11) | 0.81 (2) |
H23A | 0.7358 | 0.0985 | 0.3162 | 0.145* | 0.81 (2) |
H23B | 0.6680 | 0.0080 | 0.3451 | 0.145* | 0.81 (2) |
H23C | 0.5945 | 0.0095 | 0.2978 | 0.145* | 0.81 (2) |
O1D | −0.140 (6) | 0.268 (4) | 0.355 (2) | 0.077 (16)* | 0.19 (2) |
C7D | 0.101 (6) | 0.259 (2) | 0.3557 (9) | 0.090 (16)* | 0.19 (2) |
C21D | 0.402 (10) | 0.132 (5) | 0.3417 (12) | 0.075 (16)* | 0.19 (2) |
H21D | 0.5236 | 0.1754 | 0.3519 | 0.090* | 0.19 (2) |
C22D | 0.197 (10) | 0.157 (3) | 0.3683 (17) | 0.084 (14)* | 0.19 (2) |
H22D | 0.2378 | 0.1581 | 0.3978 | 0.101* | 0.19 (2) |
H22E | 0.0842 | 0.1055 | 0.3643 | 0.101* | 0.19 (2) |
C23D | 0.494 (16) | 0.028 (5) | 0.338 (3) | 0.11 (2)* | 0.19 (2) |
H23D | 0.6220 | 0.0287 | 0.3204 | 0.162* | 0.19 (2) |
H23E | 0.5360 | 0.0051 | 0.3659 | 0.162* | 0.19 (2) |
H23F | 0.3816 | −0.0154 | 0.3270 | 0.162* | 0.19 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.068 (6) | 0.075 (7) | 0.091 (19) | 0.002 (5) | 0.001 (8) | −0.010 (7) |
O3 | 0.079 (6) | 0.102 (8) | 0.10 (2) | −0.030 (6) | 0.016 (9) | −0.016 (8) |
N1 | 0.061 (6) | 0.057 (8) | 0.11 (3) | 0.002 (6) | −0.014 (10) | −0.011 (8) |
C15 | 0.053 (8) | 0.055 (10) | 0.14 (3) | 0.005 (8) | −0.017 (12) | −0.005 (10) |
C16 | 0.068 (9) | 0.074 (11) | 0.07 (3) | 0.010 (7) | −0.008 (12) | 0.010 (10) |
C17 | 0.060 (8) | 0.066 (11) | 0.15 (3) | −0.007 (8) | −0.001 (12) | −0.008 (11) |
C18 | 0.078 (11) | 0.085 (13) | 0.04 (3) | −0.018 (9) | 0.023 (14) | 0.007 (10) |
C19 | 0.104 (13) | 0.141 (17) | 0.04 (4) | 0.007 (12) | −0.020 (17) | 0.018 (13) |
C20 | 0.082 (11) | 0.126 (17) | 0.12 (4) | −0.021 (11) | 0.017 (15) | 0.027 (13) |
O1 | 0.108 (10) | 0.092 (12) | 0.065 (19) | −0.035 (10) | 0.017 (12) | −0.036 (10) |
C7 | 0.081 (12) | 0.086 (14) | 0.10 (3) | −0.024 (12) | −0.019 (16) | −0.012 (14) |
C21 | 0.081 (11) | 0.066 (12) | 0.073 (18) | 0.011 (10) | −0.017 (13) | 0.007 (11) |
C22 | 0.116 (16) | 0.088 (15) | 0.11 (3) | −0.022 (12) | −0.019 (18) | 0.033 (14) |
C23 | 0.087 (14) | 0.075 (14) | 0.13 (3) | 0.042 (12) | 0.024 (18) | 0.012 (13) |
O2—C14 | 1.25 (2) | C11—C14 | 1.54 (2) |
O3—C14 | 1.250 (18) | C12—C13 | 1.40 (2) |
N1—C25 | 1.54 (3) | C15—C16 | 1.49 (2) |
C1—C2 | 1.38 (2) | C15—C17 | 1.544 (17) |
C1—C6 | 1.439 (18) | C18—C20 | 1.54 (2) |
C1—C7 | 1.53 (2) | C18—C19 | 1.55 (3) |
C1—C7D | 1.57 (2) | C24—C25 | 1.52 (2) |
C2—C3 | 1.36 (3) | C25—C26 | 1.50 (2) |
C2—C15 | 1.529 (19) | C26—C27 | 1.377 (19) |
C3—C4 | 1.414 (19) | C26—C31 | 1.38 (2) |
C4—C5 | 1.43 (3) | C27—C28 | 1.393 (18) |
C4—C18 | 1.48 (3) | C28—C29 | 1.35 (2) |
C5—C6 | 1.35 (2) | C29—C30 | 1.33 (2) |
C6—C21 | 1.54 (2) | C30—C31 | 1.386 (18) |
C6—C21D | 1.54 (3) | O1—C7 | 1.231 (17) |
C8—C9 | 1.39 (2) | C21—C23 | 1.531 (19) |
C8—C13 | 1.412 (19) | C21—C22 | 1.534 (19) |
C8—C7 | 1.482 (18) | O1D—C7D | 1.45 (3) |
C8—C7D | 1.53 (2) | C7D—C22D | 1.53 (3) |
C9—C10 | 1.39 (2) | C21D—C23D | 1.49 (3) |
C10—C11 | 1.380 (18) | C21D—C22D | 1.53 (3) |
C11—C12 | 1.38 (3) | ||
C2—C1—C6 | 122.3 (18) | C16—C15—C2 | 111.9 (14) |
C2—C1—C7 | 120.6 (16) | C16—C15—C17 | 112.6 (13) |
C6—C1—C7 | 117.1 (16) | C2—C15—C17 | 109.6 (11) |
C2—C1—C7D | 125.2 (19) | C4—C18—C20 | 111.5 (19) |
C6—C1—C7D | 112.4 (19) | C4—C18—C19 | 116.1 (17) |
C3—C2—C1 | 117.9 (15) | C20—C18—C19 | 111.5 (18) |
C3—C2—C15 | 124.8 (17) | C26—C25—C24 | 117.2 (14) |
C1—C2—C15 | 117.3 (18) | C26—C25—N1 | 106.6 (18) |
C2—C3—C4 | 125 (2) | C24—C25—N1 | 107.8 (16) |
C3—C4—C5 | 113 (2) | C27—C26—C31 | 118.0 (14) |
C3—C4—C18 | 125.5 (19) | C27—C26—C25 | 123.1 (14) |
C5—C4—C18 | 121.8 (16) | C31—C26—C25 | 118.8 (15) |
C6—C5—C4 | 126.7 (17) | C26—C27—C28 | 120.3 (15) |
C5—C6—C1 | 115.3 (15) | C29—C28—C27 | 119.5 (17) |
C5—C6—C21 | 124.0 (15) | C30—C29—C28 | 121.5 (18) |
C1—C6—C21 | 120.7 (18) | C29—C30—C31 | 119.9 (18) |
C5—C6—C21D | 137 (2) | C26—C31—C30 | 120.7 (17) |
C1—C6—C21D | 107 (2) | O1—C7—C8 | 118.2 (18) |
C9—C8—C13 | 118.2 (15) | O1—C7—C1 | 122.8 (16) |
C9—C8—C7 | 120.6 (14) | C8—C7—C1 | 118.2 (15) |
C13—C8—C7 | 121.2 (17) | C23—C21—C22 | 109.2 (16) |
C9—C8—C7D | 119.7 (16) | C23—C21—C6 | 111.7 (18) |
C13—C8—C7D | 121.9 (19) | C22—C21—C6 | 109.6 (16) |
C8—C9—C10 | 121.4 (14) | O1D—C7D—C22D | 117 (3) |
C11—C10—C9 | 119.2 (18) | O1D—C7D—C8 | 110 (3) |
C12—C11—C10 | 121.7 (16) | C22D—C7D—C8 | 113 (3) |
C12—C11—C14 | 118.6 (14) | O1D—C7D—C1 | 105 (3) |
C10—C11—C14 | 119.7 (19) | C22D—C7D—C1 | 98 (3) |
C11—C12—C13 | 118.9 (14) | C8—C7D—C1 | 113 (2) |
C12—C13—C8 | 120.6 (18) | C23D—C21D—C22D | 122 (5) |
O2—C14—O3 | 124.3 (18) | C23D—C21D—C6 | 113 (4) |
O2—C14—C11 | 117.8 (15) | C22D—C21D—C6 | 100 (3) |
O3—C14—C11 | 118 (2) | C21D—C22D—C7D | 110 (3) |
C31H39NO3 | Dx = 1.242 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 836 reflections |
a = 5.9831 (15) Å | θ = 5.6–23.4° |
b = 13.294 (4) Å | µ = 0.08 mm−1 |
c = 31.84 (3) Å | T = 299 K |
V = 2533 (3) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.10 × 0.08 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 2210 independent reflections |
Radiation source: fine-focus sealed tube | 808 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.118 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 24.7°, θmin = 5.6° |
φ– and ω scans | h = −6→6 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −11→15 |
Tmin = 0.171, Tmax = 1.000 | l = −20→22 |
6242 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.086 | w = 1/[σ2(Fo2) + (0.1115P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.262 | (Δ/σ)max < 0.001 |
S = 0.99 | Δρmax = 0.16 e Å−3 |
2210 reflections | Δρmin = −0.15 e Å−3 |
198 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
65 restraints | Absolute structure parameter: −1.4 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O2 | 0.3823 (16) | 0.6240 (7) | 0.4826 (5) | 0.082 (5) | |
O3 | 0.6898 (18) | 0.6130 (7) | 0.4451 (5) | 0.096 (6) | |
N1 | 0.9559 (17) | 0.6703 (7) | 0.5092 (6) | 0.084 (8) | |
H1A | 0.9652 | 0.7370 | 0.5109 | 0.101* | |
H1B | 0.8438 | 0.6536 | 0.4922 | 0.101* | |
H1C | 1.0833 | 0.6458 | 0.4990 | 0.101* | |
C1 | 0.176 (2) | 0.2581 (10) | 0.3083 (7) | 0.068 (5)* | |
C2 | 0.097 (2) | 0.3220 (10) | 0.2780 (7) | 0.060 (4)* | |
C3 | 0.163 (2) | 0.3048 (10) | 0.2373 (8) | 0.066 (5)* | |
H3 | 0.1072 | 0.3472 | 0.2166 | 0.079* | |
C4 | 0.308 (2) | 0.2279 (10) | 0.2249 (8) | 0.067 (5)* | |
C5 | 0.385 (2) | 0.1664 (9) | 0.2583 (7) | 0.059 (4)* | |
H5 | 0.4827 | 0.1145 | 0.2515 | 0.071* | |
C6 | 0.327 (2) | 0.1769 (9) | 0.2996 (7) | 0.059 (4)* | |
C8 | 0.205 (2) | 0.3470 (10) | 0.3805 (7) | 0.062 (4)* | |
C9 | 0.098 (3) | 0.3848 (10) | 0.4151 (7) | 0.075 (5)* | |
H9 | −0.0400 | 0.3584 | 0.4228 | 0.090* | |
C10 | 0.190 (2) | 0.4608 (10) | 0.4388 (7) | 0.075 (5)* | |
H10 | 0.1137 | 0.4860 | 0.4620 | 0.090* | |
C11 | 0.396 (3) | 0.4993 (10) | 0.4277 (8) | 0.070 (5)* | |
C12 | 0.511 (3) | 0.4626 (10) | 0.3943 (8) | 0.074 (5)* | |
H12 | 0.6523 | 0.4873 | 0.3878 | 0.089* | |
C13 | 0.413 (2) | 0.3860 (10) | 0.3693 (7) | 0.075 (5)* | |
H13 | 0.4869 | 0.3620 | 0.3457 | 0.090* | |
C14 | 0.498 (3) | 0.5836 (12) | 0.4550 (8) | 0.069 (5)* | |
C15 | −0.052 (2) | 0.4080 (10) | 0.2904 (8) | 0.083 (10) | |
H15 | −0.0765 | 0.4011 | 0.3207 | 0.100* | |
C16 | −0.277 (2) | 0.4033 (10) | 0.2707 (7) | 0.071 (5)* | |
H16A | −0.3642 | 0.4600 | 0.2797 | 0.106* | |
H16B | −0.2618 | 0.4049 | 0.2407 | 0.106* | |
H16C | −0.3503 | 0.3422 | 0.2789 | 0.106* | |
C17 | 0.065 (3) | 0.5097 (9) | 0.2842 (8) | 0.086 (5)* | |
H17A | 0.2092 | 0.5080 | 0.2976 | 0.130* | |
H17B | 0.0840 | 0.5225 | 0.2548 | 0.130* | |
H17C | −0.0236 | 0.5621 | 0.2965 | 0.130* | |
C18 | 0.372 (3) | 0.2031 (12) | 0.1819 (9) | 0.083 (5)* | |
H18 | 0.3605 | 0.1298 | 0.1796 | 0.100* | |
C19 | 0.219 (3) | 0.2462 (13) | 0.1470 (9) | 0.125 (8)* | |
H19A | 0.2746 | 0.2258 | 0.1200 | 0.188* | |
H19B | 0.0698 | 0.2213 | 0.1507 | 0.188* | |
H19C | 0.2182 | 0.3183 | 0.1487 | 0.188* | |
C20 | 0.617 (3) | 0.2294 (12) | 0.1724 (9) | 0.108 (7)* | |
H20A | 0.6511 | 0.2119 | 0.1438 | 0.161* | |
H20B | 0.6400 | 0.3002 | 0.1764 | 0.161* | |
H20C | 0.7131 | 0.1925 | 0.1910 | 0.161* | |
C24 | 0.691 (2) | 0.6654 (10) | 0.5692 (8) | 0.093 (6)* | |
H24A | 0.6958 | 0.7375 | 0.5707 | 0.140* | |
H24B | 0.5739 | 0.6453 | 0.5503 | 0.140* | |
H24C | 0.6618 | 0.6384 | 0.5966 | 0.140* | |
C25 | 0.913 (3) | 0.6261 (12) | 0.5533 (9) | 0.088 (6)* | |
H25 | 1.0311 | 0.6499 | 0.5722 | 0.105* | |
C26 | 0.933 (2) | 0.5138 (10) | 0.5490 (8) | 0.076 (5)* | |
C27 | 0.762 (2) | 0.4525 (12) | 0.5340 (8) | 0.085 (6)* | |
H27 | 0.6293 | 0.4813 | 0.5246 | 0.102* | |
C28 | 0.789 (3) | 0.3487 (13) | 0.5330 (9) | 0.096 (6)* | |
H28 | 0.6699 | 0.3078 | 0.5250 | 0.115* | |
C29 | 0.987 (3) | 0.3072 (13) | 0.5436 (8) | 0.101 (6)* | |
H29 | 1.0039 | 0.2378 | 0.5422 | 0.121* | |
C30 | 1.158 (3) | 0.3641 (12) | 0.5559 (9) | 0.102 (6)* | |
H30 | 1.2947 | 0.3344 | 0.5625 | 0.122* | |
C31 | 1.133 (3) | 0.4676 (11) | 0.5590 (9) | 0.093 (6)* | |
H31 | 1.2525 | 0.5066 | 0.5680 | 0.112* | |
O1 | −0.066 (3) | 0.2244 (13) | 0.3673 (7) | 0.092 (8) | 0.77 (2) |
C7 | 0.096 (4) | 0.2690 (16) | 0.3539 (7) | 0.097 (9) | 0.77 (2) |
C21 | 0.405 (3) | 0.1057 (15) | 0.3340 (8) | 0.073 (7) | 0.77 (2) |
H21 | 0.4257 | 0.1457 | 0.3595 | 0.087* | 0.77 (2) |
C22 | 0.224 (4) | 0.0280 (15) | 0.3432 (11) | 0.108 (9)* | 0.77 (2) |
H22A | 0.0853 | 0.0618 | 0.3487 | 0.162* | 0.77 (2) |
H22B | 0.2067 | −0.0156 | 0.3194 | 0.162* | 0.77 (2) |
H22C | 0.2661 | −0.0110 | 0.3673 | 0.162* | 0.77 (2) |
C23 | 0.624 (3) | 0.0523 (15) | 0.3253 (9) | 0.083 (8)* | 0.77 (2) |
H23A | 0.6604 | 0.0092 | 0.3485 | 0.124* | 0.77 (2) |
H23B | 0.6103 | 0.0128 | 0.3002 | 0.124* | 0.77 (2) |
H23C | 0.7408 | 0.1012 | 0.3216 | 0.124* | 0.77 (2) |
O1D | −0.138 (5) | 0.264 (4) | 0.3565 (19) | 0.076 (15)* | 0.23 (2) |
C7D | 0.104 (6) | 0.258 (2) | 0.3560 (9) | 0.094 (15)* | 0.23 (2) |
C21D | 0.398 (10) | 0.128 (4) | 0.3410 (11) | 0.075 (15)* | 0.23 (2) |
H21D | 0.5252 | 0.1671 | 0.3515 | 0.090* | 0.23 (2) |
C22D | 0.199 (9) | 0.155 (3) | 0.3685 (16) | 0.083 (14)* | 0.23 (2) |
H22D | 0.2453 | 0.1573 | 0.3977 | 0.099* | 0.23 (2) |
H22E | 0.0840 | 0.1045 | 0.3656 | 0.099* | 0.23 (2) |
C23D | 0.482 (13) | 0.023 (4) | 0.335 (2) | 0.09 (2)* | 0.23 (2) |
H23D | 0.6081 | 0.0231 | 0.3167 | 0.141* | 0.23 (2) |
H23E | 0.5250 | −0.0045 | 0.3620 | 0.141* | 0.23 (2) |
H23F | 0.3650 | −0.0180 | 0.3234 | 0.141* | 0.23 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.077 (7) | 0.084 (8) | 0.084 (19) | 0.002 (6) | 0.002 (9) | −0.012 (7) |
O3 | 0.083 (7) | 0.110 (9) | 0.09 (2) | −0.028 (7) | 0.016 (9) | −0.016 (8) |
N1 | 0.061 (7) | 0.059 (8) | 0.13 (3) | −0.007 (6) | −0.010 (10) | −0.013 (8) |
C15 | 0.056 (8) | 0.072 (11) | 0.12 (3) | −0.003 (8) | −0.016 (12) | −0.007 (10) |
O1 | 0.119 (12) | 0.095 (13) | 0.063 (19) | −0.040 (11) | 0.026 (13) | −0.027 (10) |
C7 | 0.092 (15) | 0.103 (15) | 0.10 (3) | −0.023 (14) | 0.005 (18) | −0.006 (15) |
C21 | 0.078 (11) | 0.064 (12) | 0.075 (18) | 0.009 (10) | −0.005 (13) | −0.010 (10) |
O2—C14 | 1.24 (2) | C11—C14 | 1.54 (3) |
O3—C14 | 1.254 (19) | C12—C13 | 1.42 (2) |
N1—C25 | 1.54 (3) | C15—C16 | 1.487 (19) |
C1—C2 | 1.37 (2) | C15—C17 | 1.536 (17) |
C1—C6 | 1.433 (18) | C18—C20 | 1.54 (2) |
C1—C7 | 1.54 (2) | C18—C19 | 1.55 (3) |
C1—C7D | 1.58 (2) | C24—C25 | 1.52 (2) |
C2—C3 | 1.37 (3) | C25—C26 | 1.51 (2) |
C2—C15 | 1.503 (18) | C26—C31 | 1.38 (2) |
C3—C4 | 1.399 (18) | C26—C27 | 1.39 (2) |
C4—C5 | 1.42 (2) | C27—C28 | 1.390 (18) |
C4—C18 | 1.46 (3) | C28—C29 | 1.35 (2) |
C5—C6 | 1.37 (2) | C29—C30 | 1.33 (2) |
C6—C21 | 1.52 (2) | C30—C31 | 1.388 (18) |
C6—C21D | 1.53 (2) | O1—C7 | 1.213 (17) |
C8—C9 | 1.37 (2) | C21—C23 | 1.516 (19) |
C8—C13 | 1.397 (19) | C21—C22 | 1.52 (2) |
C8—C7 | 1.490 (19) | O1D—C7D | 1.45 (3) |
C8—C7D | 1.54 (2) | C7D—C22D | 1.53 (3) |
C9—C10 | 1.375 (19) | C21D—C23D | 1.49 (3) |
C10—C11 | 1.382 (19) | C21D—C22D | 1.52 (3) |
C11—C12 | 1.36 (3) | ||
C2—C1—C6 | 123.2 (18) | C16—C15—C2 | 113.3 (14) |
C2—C1—C7 | 119.9 (16) | C16—C15—C17 | 113.4 (13) |
C6—C1—C7 | 116.8 (16) | C2—C15—C17 | 111.4 (11) |
C2—C1—C7D | 125.7 (18) | C4—C18—C20 | 112.4 (19) |
C6—C1—C7D | 110.9 (18) | C4—C18—C19 | 115.9 (16) |
C1—C2—C3 | 117.5 (15) | C20—C18—C19 | 109.7 (19) |
C1—C2—C15 | 119.5 (18) | C26—C25—C24 | 116.3 (14) |
C3—C2—C15 | 123.0 (16) | C26—C25—N1 | 106.3 (18) |
C2—C3—C4 | 124.5 (19) | C24—C25—N1 | 108.6 (16) |
C3—C4—C5 | 114 (2) | C31—C26—C27 | 117.1 (15) |
C3—C4—C18 | 126.3 (19) | C31—C26—C25 | 119.4 (16) |
C5—C4—C18 | 119.3 (15) | C27—C26—C25 | 123.4 (14) |
C6—C5—C4 | 125.4 (16) | C28—C27—C26 | 120.2 (16) |
C5—C6—C1 | 115.0 (14) | C29—C28—C27 | 120.0 (17) |
C5—C6—C21 | 123.4 (15) | C30—C29—C28 | 121.2 (18) |
C1—C6—C21 | 121.5 (18) | C29—C30—C31 | 119.9 (18) |
C5—C6—C21D | 135.5 (18) | C26—C31—C30 | 121.4 (18) |
C1—C6—C21D | 109.3 (19) | O1—C7—C8 | 119.1 (19) |
C9—C8—C13 | 119.0 (15) | O1—C7—C1 | 122.5 (17) |
C9—C8—C7 | 120.7 (14) | C8—C7—C1 | 117.9 (16) |
C13—C8—C7 | 120.2 (17) | C23—C21—C6 | 115.2 (19) |
C9—C8—C7D | 120.5 (16) | C23—C21—C22 | 109.5 (15) |
C13—C8—C7D | 120.3 (18) | C6—C21—C22 | 109.9 (17) |
C8—C9—C10 | 121.6 (14) | O1D—C7D—C22D | 115 (3) |
C9—C10—C11 | 119.3 (19) | O1D—C7D—C8 | 110 (3) |
C12—C11—C10 | 121.3 (17) | C22D—C7D—C8 | 114 (3) |
C12—C11—C14 | 120.1 (15) | O1D—C7D—C1 | 107 (3) |
C10—C11—C14 | 119 (2) | C22D—C7D—C1 | 99 (2) |
C11—C12—C13 | 119.2 (15) | C8—C7D—C1 | 112 (2) |
C8—C13—C12 | 119.5 (18) | C23D—C21D—C22D | 124 (4) |
O2—C14—O3 | 123.7 (18) | C23D—C21D—C6 | 113 (4) |
O2—C14—C11 | 119.6 (16) | C22D—C21D—C6 | 100 (3) |
O3—C14—C11 | 116 (2) | C21D—C22D—C7D | 111 (3) |
C31H39NO3 | Dx = 1.243 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 926 reflections |
a = 5.9808 (13) Å | θ = 5.6–21.7° |
b = 13.293 (4) Å | µ = 0.08 mm−1 |
c = 31.84 (3) Å | T = 299 K |
V = 2531 (3) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.10 × 0.08 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 2248 independent reflections |
Radiation source: fine-focus sealed tube | 852 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.144 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 24.7°, θmin = 5.6° |
φ– and ω scans | h = −6→6 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −11→15 |
Tmin = 0.337, Tmax = 1.000 | l = −20→23 |
7206 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.085 | w = 1/[σ2(Fo2) + (0.0916P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.236 | (Δ/σ)max = 0.001 |
S = 0.99 | Δρmax = 0.16 e Å−3 |
2248 reflections | Δρmin = −0.15 e Å−3 |
200 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
154 restraints | Absolute structure parameter: −2.4 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O2 | 0.3799 (14) | 0.6235 (6) | 0.4828 (4) | 0.078 (5) | |
O3 | 0.6898 (15) | 0.6126 (7) | 0.4450 (5) | 0.098 (6) | |
C1 | 0.1780 (19) | 0.2568 (9) | 0.3082 (5) | 0.0582 (18)* | |
C2 | 0.1001 (19) | 0.3211 (9) | 0.2775 (6) | 0.0582 (18)* | |
C3 | 0.1636 (19) | 0.3056 (9) | 0.2360 (7) | 0.0582 (18)* | |
H3 | 0.1091 | 0.3484 | 0.2154 | 0.070* | |
C4 | 0.3067 (19) | 0.2276 (9) | 0.2246 (7) | 0.0582 (18)* | |
C5 | 0.3877 (18) | 0.1657 (9) | 0.2580 (6) | 0.0582 (18)* | |
H5 | 0.4876 | 0.1145 | 0.2513 | 0.070* | |
C6 | 0.328 (2) | 0.1768 (9) | 0.2984 (6) | 0.0582 (18)* | |
C14 | 0.498 (3) | 0.5852 (11) | 0.4543 (7) | 0.070 (5)* | |
C18 | 0.372 (2) | 0.2038 (10) | 0.1818 (8) | 0.075 (5)* | |
H18 | 0.3604 | 0.1304 | 0.1795 | 0.091* | |
C19 | 0.619 (2) | 0.2286 (11) | 0.1729 (8) | 0.107 (6)* | |
H19A | 0.6540 | 0.2117 | 0.1443 | 0.161* | |
H19B | 0.6442 | 0.2991 | 0.1773 | 0.161* | |
H19C | 0.7126 | 0.1905 | 0.1915 | 0.161* | |
C20 | 0.218 (2) | 0.2456 (12) | 0.1471 (8) | 0.118 (7)* | |
H20A | 0.2748 | 0.2260 | 0.1201 | 0.177* | |
H20B | 0.0700 | 0.2192 | 0.1507 | 0.177* | |
H20C | 0.2140 | 0.3177 | 0.1489 | 0.177* | |
C26 | 0.9382 (8) | 0.5130 (4) | 0.5487 (3) | 0.070 (4)* | |
N1 | 0.9529 (13) | 0.6722 (4) | 0.5093 (4) | 0.077 (6) | |
H1A | 0.8485 | 0.6506 | 0.4915 | 0.092* | |
H1B | 1.0873 | 0.6546 | 0.4998 | 0.092* | |
H1C | 0.9454 | 0.7389 | 0.5114 | 0.092* | |
C24 | 0.6956 (15) | 0.6627 (5) | 0.5691 (4) | 0.087 (5)* | |
H24A | 0.5767 | 0.6447 | 0.5503 | 0.130* | |
H24B | 0.7005 | 0.7345 | 0.5722 | 0.130* | |
H24C | 0.6696 | 0.6324 | 0.5961 | 0.130* | |
C25 | 0.9150 (10) | 0.6259 (4) | 0.5517 (3) | 0.088 (5)* | |
H25 | 1.0336 | 0.6502 | 0.5703 | 0.106* | |
C27 | 1.1324 (10) | 0.4663 (5) | 0.5613 (4) | 0.089 (5)* | |
H27 | 1.2510 | 0.5050 | 0.5711 | 0.107* | |
C28 | 1.1537 (13) | 0.3626 (5) | 0.5595 (4) | 0.101 (5)* | |
H28 | 1.2855 | 0.3321 | 0.5684 | 0.121* | |
C29 | 0.9837 (15) | 0.3056 (4) | 0.5451 (4) | 0.105 (6)* | |
H29 | 0.9992 | 0.2361 | 0.5438 | 0.126* | |
C30 | 0.7889 (14) | 0.3498 (4) | 0.5323 (4) | 0.095 (5)* | |
H30 | 0.6716 | 0.3103 | 0.5225 | 0.114* | |
C31 | 0.7661 (9) | 0.4538 (4) | 0.5339 (4) | 0.084 (5)* | |
H31 | 0.6339 | 0.4837 | 0.5249 | 0.101* | |
O1 | −0.062 (3) | 0.2221 (12) | 0.3676 (7) | 0.080 (7) | 0.675 (4) |
C7 | 0.097 (3) | 0.2686 (15) | 0.3535 (7) | 0.075 (8)* | 0.675 (4) |
C8 | 0.204 (2) | 0.3460 (10) | 0.3801 (6) | 0.055 (4)* | 0.675 (4) |
C9 | 0.096 (2) | 0.3806 (10) | 0.4164 (6) | 0.062 (5)* | 0.675 (4) |
H9 | −0.0383 | 0.3518 | 0.4250 | 0.074* | 0.675 (4) |
C10 | 0.190 (2) | 0.4574 (10) | 0.4390 (7) | 0.064 (5)* | 0.675 (4) |
H10 | 0.1137 | 0.4829 | 0.4621 | 0.076* | 0.675 (4) |
C11 | 0.395 (2) | 0.4981 (11) | 0.4283 (8) | 0.058 (5)* | 0.675 (4) |
C12 | 0.510 (2) | 0.4611 (11) | 0.3951 (8) | 0.063 (5)* | 0.675 (4) |
H12 | 0.6514 | 0.4860 | 0.3887 | 0.075* | 0.675 (4) |
C13 | 0.415 (2) | 0.3852 (10) | 0.3706 (7) | 0.067 (5)* | 0.675 (4) |
H13 | 0.4928 | 0.3604 | 0.3476 | 0.081* | 0.675 (4) |
C15 | −0.053 (2) | 0.4098 (9) | 0.2899 (7) | 0.068 (5) | 0.675 (4) |
H15 | −0.0801 | 0.4043 | 0.3202 | 0.082* | 0.675 (4) |
C16 | −0.279 (2) | 0.4033 (10) | 0.2685 (8) | 0.065 (5)* | 0.675 (4) |
H16A | −0.3452 | 0.3389 | 0.2742 | 0.098* | 0.675 (4) |
H16B | −0.3748 | 0.4555 | 0.2791 | 0.098* | 0.675 (4) |
H16C | −0.2603 | 0.4115 | 0.2388 | 0.098* | 0.675 (4) |
C17 | 0.064 (3) | 0.5108 (10) | 0.2824 (9) | 0.075 (5)* | 0.675 (4) |
H17A | 0.2053 | 0.5111 | 0.2965 | 0.113* | 0.675 (4) |
H17B | 0.0866 | 0.5203 | 0.2528 | 0.113* | 0.675 (4) |
H17C | −0.0279 | 0.5643 | 0.2931 | 0.113* | 0.675 (4) |
C21 | 0.405 (3) | 0.1061 (14) | 0.3334 (7) | 0.073 (6) | 0.675 (4) |
H21 | 0.4277 | 0.1468 | 0.3587 | 0.087* | 0.675 (4) |
C22 | 0.222 (3) | 0.0284 (15) | 0.3434 (11) | 0.120 (8)* | 0.675 (4) |
H22A | 0.0836 | 0.0626 | 0.3491 | 0.179* | 0.675 (4) |
H22B | 0.2024 | −0.0157 | 0.3198 | 0.179* | 0.675 (4) |
H22C | 0.2651 | −0.0102 | 0.3676 | 0.179* | 0.675 (4) |
C23 | 0.621 (3) | 0.0509 (13) | 0.3245 (9) | 0.080 (7)* | 0.675 (4) |
H23A | 0.6566 | 0.0082 | 0.3479 | 0.120* | 0.675 (4) |
H23B | 0.6035 | 0.0106 | 0.2997 | 0.120* | 0.675 (4) |
H23C | 0.7387 | 0.0987 | 0.3203 | 0.120* | 0.675 (4) |
O1D | −0.137 (5) | 0.264 (4) | 0.3545 (18) | 0.079 (19)* | 0.230 (4) |
C7D | 0.106 (6) | 0.257 (2) | 0.3557 (8) | 0.076 (18)* | 0.230 (4) |
C8D | 0.204 (2) | 0.3460 (10) | 0.3801 (6) | 0.055 (4)* | 0.230 (4) |
C9D | 0.096 (2) | 0.3806 (10) | 0.4164 (6) | 0.062 (5)* | 0.230 (4) |
H9D | −0.0383 | 0.3518 | 0.4250 | 0.074* | 0.230 (4) |
C10D | 0.190 (2) | 0.4574 (10) | 0.4390 (7) | 0.064 (5)* | 0.230 (4) |
H10D | 0.1137 | 0.4829 | 0.4621 | 0.076* | 0.230 (4) |
C11D | 0.395 (2) | 0.4981 (11) | 0.4283 (8) | 0.058 (5)* | 0.230 (4) |
C12D | 0.510 (2) | 0.4611 (11) | 0.3951 (8) | 0.063 (5)* | 0.230 (4) |
H12D | 0.6514 | 0.4860 | 0.3887 | 0.075* | 0.230 (4) |
C13D | 0.415 (2) | 0.3852 (10) | 0.3706 (7) | 0.067 (5)* | 0.230 (4) |
H13D | 0.4928 | 0.3604 | 0.3476 | 0.081* | 0.230 (4) |
C15D | −0.053 (2) | 0.4098 (9) | 0.2899 (7) | 0.068 (5) | 0.230 (4) |
H15D | −0.0801 | 0.4043 | 0.3202 | 0.082* | 0.230 (4) |
C16D | −0.279 (2) | 0.4033 (10) | 0.2685 (8) | 0.065 (5)* | 0.230 (4) |
H16D | −0.3452 | 0.3389 | 0.2742 | 0.098* | 0.230 (4) |
H16E | −0.3748 | 0.4555 | 0.2791 | 0.098* | 0.230 (4) |
H16F | −0.2603 | 0.4115 | 0.2388 | 0.098* | 0.230 (4) |
C17D | 0.064 (3) | 0.5108 (10) | 0.2824 (9) | 0.075 (5)* | 0.230 (4) |
H17D | 0.2053 | 0.5111 | 0.2965 | 0.113* | 0.230 (4) |
H17E | 0.0866 | 0.5203 | 0.2528 | 0.113* | 0.230 (4) |
H17F | −0.0279 | 0.5643 | 0.2931 | 0.113* | 0.230 (4) |
C21D | 0.402 (9) | 0.128 (4) | 0.3397 (10) | 0.076 (11)* | 0.230 (4) |
H21D | 0.5289 | 0.1676 | 0.3498 | 0.091* | 0.230 (4) |
C22D | 0.206 (8) | 0.155 (3) | 0.3679 (15) | 0.10 (2)* | 0.230 (4) |
H22D | 0.2554 | 0.1573 | 0.3969 | 0.122* | 0.230 (4) |
H22E | 0.0915 | 0.1034 | 0.3657 | 0.122* | 0.230 (4) |
C23D | 0.486 (12) | 0.023 (4) | 0.334 (2) | 0.10 (2)* | 0.230 (4) |
H23D | 0.6098 | 0.0229 | 0.3153 | 0.149* | 0.230 (4) |
H23E | 0.5328 | −0.0028 | 0.3612 | 0.149* | 0.230 (4) |
H23F | 0.3682 | −0.0186 | 0.3234 | 0.149* | 0.230 (4) |
O1P | −0.110 (14) | 0.258 (7) | 0.365 (2) | 0.09 (3)* | 0.096 (4) |
C7P | 0.044 (7) | 0.312 (3) | 0.3410 (11) | 0.07 (2)* | 0.096 (4) |
C8P | 0.164 (7) | 0.384 (2) | 0.3709 (11) | 0.056 (19)* | 0.096 (4) |
C9P | 0.056 (7) | 0.422 (5) | 0.4038 (17) | 0.069 (19)* | 0.096 (4) |
H9P | −0.0914 | 0.4027 | 0.4089 | 0.082* | 0.096 (4) |
C10P | 0.160 (9) | 0.489 (7) | 0.430 (2) | 0.049 (19)* | 0.096 (4) |
H10P | 0.0846 | 0.5137 | 0.4539 | 0.059* | 0.096 (4) |
C11P | 0.376 (9) | 0.521 (7) | 0.422 (2) | 0.061 (19)* | 0.096 (4) |
C12P | 0.489 (9) | 0.483 (7) | 0.388 (2) | 0.055 (19)* | 0.096 (4) |
H12P | 0.6359 | 0.5025 | 0.3826 | 0.067* | 0.096 (4) |
C13P | 0.385 (9) | 0.414 (6) | 0.3612 (17) | 0.067 (19)* | 0.096 (4) |
H13P | 0.4587 | 0.3892 | 0.3377 | 0.081* | 0.096 (4) |
C15P | −0.047 (8) | 0.388 (4) | 0.3036 (14) | 0.071 (12)* | 0.096 (4) |
C16P | −0.296 (8) | 0.383 (8) | 0.297 (3) | 0.09 (3)* | 0.096 (4) |
H16G | −0.3683 | 0.4293 | 0.3156 | 0.135* | 0.096 (4) |
H16H | −0.3293 | 0.4010 | 0.2683 | 0.135* | 0.096 (4) |
H16I | −0.3478 | 0.3161 | 0.3023 | 0.135* | 0.096 (4) |
C17P | 0.043 (17) | 0.495 (3) | 0.306 (3) | 0.05 (3)* | 0.096 (4) |
H17G | −0.0561 | 0.5349 | 0.3234 | 0.076* | 0.096 (4) |
H17H | 0.1889 | 0.4944 | 0.3189 | 0.076* | 0.096 (4) |
H17I | 0.0516 | 0.5236 | 0.2788 | 0.076* | 0.096 (4) |
C21P | 0.405 (3) | 0.1061 (14) | 0.3334 (7) | 0.073 (6) | 0.096 (4) |
H21P | 0.4277 | 0.1468 | 0.3587 | 0.087* | 0.096 (4) |
C22P | 0.222 (3) | 0.0284 (15) | 0.3434 (11) | 0.120 (8)* | 0.096 (4) |
H22F | 0.0836 | 0.0626 | 0.3491 | 0.179* | 0.096 (4) |
H22G | 0.2024 | −0.0157 | 0.3198 | 0.179* | 0.096 (4) |
H22H | 0.2651 | −0.0102 | 0.3676 | 0.179* | 0.096 (4) |
C23P | 0.621 (3) | 0.0509 (13) | 0.3245 (9) | 0.080 (7)* | 0.096 (4) |
H23G | 0.6566 | 0.0082 | 0.3479 | 0.120* | 0.096 (4) |
H23H | 0.6035 | 0.0106 | 0.2997 | 0.120* | 0.096 (4) |
H23I | 0.7387 | 0.0987 | 0.3203 | 0.120* | 0.096 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.077 (6) | 0.073 (7) | 0.084 (17) | 0.001 (5) | 0.010 (8) | −0.019 (6) |
O3 | 0.075 (6) | 0.105 (8) | 0.11 (2) | −0.029 (6) | 0.011 (8) | −0.025 (8) |
N1 | 0.078 (7) | 0.054 (7) | 0.10 (2) | 0.001 (5) | −0.009 (9) | −0.005 (7) |
O1 | 0.104 (12) | 0.084 (13) | 0.05 (2) | −0.031 (11) | 0.028 (13) | −0.020 (11) |
C15 | 0.074 (8) | 0.047 (8) | 0.085 (15) | 0.002 (7) | −0.010 (10) | 0.004 (8) |
C21 | 0.080 (10) | 0.065 (11) | 0.072 (15) | 0.013 (9) | 0.001 (11) | 0.003 (10) |
C15D | 0.074 (8) | 0.047 (8) | 0.085 (15) | 0.002 (7) | −0.010 (10) | 0.004 (8) |
C21P | 0.080 (10) | 0.065 (11) | 0.072 (15) | 0.013 (9) | 0.001 (11) | 0.003 (10) |
O2—C14 | 1.26 (2) | C8—C9 | 1.40 (2) |
O3—C14 | 1.239 (16) | C9—C10 | 1.369 (18) |
C1—C2 | 1.380 (18) | C10—C11 | 1.386 (18) |
C1—C6 | 1.427 (15) | C11—C12 | 1.35 (3) |
C1—C7P | 1.50 (2) | C12—C13 | 1.40 (2) |
C1—C7 | 1.53 (2) | C15—C16 | 1.515 (19) |
C1—C7D | 1.57 (2) | C15—C17 | 1.533 (17) |
C2—C3 | 1.39 (2) | C21—C23 | 1.512 (18) |
C2—C15P | 1.50 (2) | C21—C22 | 1.54 (2) |
C2—C15 | 1.545 (18) | O1D—C7D | 1.45 (3) |
C2—C15D | 1.545 (18) | C7D—C22D | 1.53 (3) |
C3—C4 | 1.393 (15) | C7D—C8D | 1.54 (2) |
C4—C5 | 1.43 (2) | C8D—C13D | 1.394 (18) |
C4—C18 | 1.45 (3) | C8D—C9D | 1.40 (2) |
C5—C6 | 1.34 (2) | C9D—C10D | 1.369 (18) |
C6—C21P | 1.526 (19) | C10D—C11D | 1.386 (18) |
C6—C21 | 1.526 (19) | C11D—C12D | 1.35 (3) |
C6—C21D | 1.53 (2) | C12D—C13D | 1.40 (2) |
C14—C11P | 1.52 (2) | C15D—C16D | 1.515 (19) |
C14—C11 | 1.55 (2) | C15D—C17D | 1.533 (17) |
C14—C11D | 1.55 (2) | C21D—C23D | 1.49 (3) |
C18—C20 | 1.54 (2) | C21D—C22D | 1.52 (3) |
C18—C19 | 1.541 (18) | O1P—C7P | 1.40 (3) |
C26—C27 | 1.3764 | C7P—C8P | 1.53 (2) |
C26—C31 | 1.3785 | C7P—C15P | 1.65 (3) |
C26—C25 | 1.5097 | C8P—C9P | 1.3282 |
N1—C25 | 1.5013 | C8P—C13P | 1.4209 |
C24—C25 | 1.5071 | C9P—C10P | 1.3841 |
C27—C28 | 1.3864 | C10P—C11P | 1.3855 |
C28—C29 | 1.3481 | C11P—C12P | 1.3815 |
C29—C30 | 1.3674 | C12P—C13P | 1.3894 |
C30—C31 | 1.3911 | C15P—C16P | 1.51 (3) |
O1—C7 | 1.220 (17) | C15P—C17P | 1.53 (3) |
C7—C8 | 1.479 (18) | C21P—C23P | 1.512 (18) |
C8—C13 | 1.394 (18) | C21P—C22P | 1.54 (2) |
C2—C1—C6 | 121.4 (15) | C10—C11—C14 | 120.8 (19) |
C2—C1—C7P | 90.7 (19) | C11—C12—C13 | 119.4 (14) |
C6—C1—C7P | 148 (2) | C8—C13—C12 | 121.2 (18) |
C2—C1—C7 | 119.9 (14) | C16—C15—C17 | 112.7 (13) |
C6—C1—C7 | 118.7 (14) | C16—C15—C2 | 111.8 (13) |
C2—C1—C7D | 126.1 (17) | C17—C15—C2 | 110.9 (11) |
C6—C1—C7D | 112.4 (17) | C23—C21—C6 | 114.7 (18) |
C1—C2—C3 | 119.3 (13) | C23—C21—C22 | 108.7 (14) |
C1—C2—C15P | 100 (2) | C6—C21—C22 | 110.7 (16) |
C3—C2—C15P | 141 (2) | O1D—C7D—C22D | 117 (3) |
C1—C2—C15 | 119.4 (16) | O1D—C7D—C8D | 110 (3) |
C3—C2—C15 | 121.3 (14) | C22D—C7D—C8D | 114 (3) |
C1—C2—C15D | 119.4 (16) | O1D—C7D—C1 | 104 (3) |
C3—C2—C15D | 121.3 (14) | C22D—C7D—C1 | 98 (2) |
C2—C3—C4 | 121.9 (17) | C8D—C7D—C1 | 112.3 (19) |
C3—C4—C5 | 116.2 (19) | C13D—C8D—C9D | 118.2 (15) |
C3—C4—C18 | 124.9 (17) | C13D—C8D—C7D | 121.8 (18) |
C5—C4—C18 | 118.8 (14) | C9D—C8D—C7D | 119.4 (15) |
C6—C5—C4 | 124.1 (14) | C10D—C9D—C8D | 119.1 (13) |
C5—C6—C1 | 117.2 (13) | C9D—C10D—C11D | 121.8 (17) |
C5—C6—C21P | 123.5 (14) | C12D—C11D—C10D | 120.0 (16) |
C1—C6—C21P | 119.2 (16) | C12D—C11D—C14 | 119.2 (14) |
C5—C6—C21 | 123.5 (14) | C10D—C11D—C14 | 120.8 (19) |
C1—C6—C21 | 119.2 (16) | C11D—C12D—C13D | 119.4 (14) |
C5—C6—C21D | 134.5 (17) | C8D—C13D—C12D | 121.2 (18) |
C1—C6—C21D | 108.0 (18) | C16D—C15D—C17D | 112.7 (13) |
O3—C14—O2 | 125.0 (16) | C16D—C15D—C2 | 111.8 (13) |
O3—C14—C11P | 117 (2) | C17D—C15D—C2 | 110.9 (11) |
O2—C14—C11P | 116 (2) | C23D—C21D—C22D | 123 (4) |
O3—C14—C11 | 117.3 (18) | C23D—C21D—C6 | 113 (4) |
O2—C14—C11 | 117.7 (15) | C22D—C21D—C6 | 101 (3) |
O3—C14—C11D | 117.3 (18) | C21D—C22D—C7D | 111 (3) |
O2—C14—C11D | 117.7 (15) | O1P—C7P—C1 | 119 (4) |
C4—C18—C20 | 115.7 (14) | O1P—C7P—C8P | 107 (3) |
C4—C18—C19 | 112.5 (17) | C1—C7P—C8P | 119 (2) |
C20—C18—C19 | 111.3 (17) | O1P—C7P—C15P | 120 (4) |
C27—C26—C31 | 118.2 | C1—C7P—C15P | 88.3 (18) |
C27—C26—C25 | 120.5 | C8P—C7P—C15P | 103 (2) |
C31—C26—C25 | 121.3 | C9P—C8P—C13P | 121.1 |
N1—C25—C24 | 109.3 | C9P—C8P—C7P | 120 (2) |
N1—C25—C26 | 109.8 | C13P—C8P—C7P | 119 (2) |
C24—C25—C26 | 115.2 | C8P—C9P—C10P | 120.75 (8) |
C26—C27—C28 | 120.9 | C9P—C10P—C11P | 119.9 |
C29—C28—C27 | 120.2 | C12P—C11P—C10P | 119.88 (6) |
C28—C29—C30 | 120.2 | C12P—C11P—C14 | 120 (3) |
C29—C30—C31 | 119.9 | C10P—C11P—C14 | 119 (3) |
C26—C31—C30 | 120.5 | C11P—C12P—C13P | 120.14 (9) |
O1—C7—C8 | 118.8 (19) | C12P—C13P—C8P | 118.2 |
O1—C7—C1 | 122.7 (17) | C2—C15P—C16P | 118 (4) |
C8—C7—C1 | 118.2 (15) | C2—C15P—C17P | 112 (4) |
C13—C8—C9 | 118.2 (15) | C16P—C15P—C17P | 113 (3) |
C13—C8—C7 | 121.9 (17) | C2—C15P—C7P | 81.2 (18) |
C9—C8—C7 | 119.9 (13) | C16P—C15P—C7P | 114 (4) |
C10—C9—C8 | 119.1 (13) | C17P—C15P—C7P | 114 (4) |
C9—C10—C11 | 121.8 (17) | C23P—C21P—C6 | 114.7 (18) |
C12—C11—C10 | 120.0 (16) | C23P—C21P—C22P | 108.7 (14) |
C12—C11—C14 | 119.2 (14) | C6—C21P—C22P | 110.7 (16) |
C31H39NO3 | Dx = 1.245 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 601 reflections |
a = 5.9870 (15) Å | θ = 5.7–21.7° |
b = 13.257 (5) Å | µ = 0.08 mm−1 |
c = 31.84 (3) Å | T = 299 K |
V = 2527 (3) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.10 × 0.08 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 2199 independent reflections |
Radiation source: fine-focus sealed tube | 741 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.142 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 24.7°, θmin = 5.6° |
φ– and ω scans | h = −6→6 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −14→11 |
Tmin = 0.352, Tmax = 1.000 | l = −20→23 |
5410 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.100 | w = 1/[σ2(Fo2) + (0.1008P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.280 | (Δ/σ)max < 0.001 |
S = 0.99 | Δρmax = 0.16 e Å−3 |
2199 reflections | Δρmin = −0.16 e Å−3 |
177 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
154 restraints | Absolute structure parameter: 0.2 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C26 | 0.9387 (10) | 0.5134 (5) | 0.5485 (4) | 0.088 (6)* | |
N1 | 0.9532 (15) | 0.6731 (5) | 0.5090 (4) | 0.076 (4)* | |
H1A | 0.8494 | 0.6514 | 0.4912 | 0.092* | |
H1B | 1.0878 | 0.6556 | 0.4996 | 0.092* | |
H1C | 0.9452 | 0.7400 | 0.5111 | 0.092* | |
C24 | 0.6948 (18) | 0.6632 (6) | 0.5686 (5) | 0.096 (6)* | |
H24A | 0.5766 | 0.6450 | 0.5497 | 0.144* | |
H24B | 0.6991 | 0.7353 | 0.5717 | 0.144* | |
H24C | 0.6684 | 0.6327 | 0.5956 | 0.144* | |
C25 | 0.9147 (12) | 0.6266 (5) | 0.5514 (4) | 0.097 (6)* | |
H25 | 1.0325 | 0.6511 | 0.5701 | 0.117* | |
C27 | 1.1327 (13) | 0.4669 (6) | 0.5612 (5) | 0.099 (6)* | |
H27 | 1.2507 | 0.5058 | 0.5711 | 0.119* | |
C28 | 1.1547 (16) | 0.3629 (6) | 0.5594 (5) | 0.107 (7)* | |
H28 | 1.2864 | 0.3325 | 0.5684 | 0.129* | |
C29 | 0.9857 (19) | 0.3056 (5) | 0.5448 (5) | 0.112 (7)* | |
H29 | 1.0017 | 0.2358 | 0.5436 | 0.134* | |
C30 | 0.7910 (17) | 0.3496 (5) | 0.5318 (5) | 0.107 (7)* | |
H30 | 0.6744 | 0.3098 | 0.5220 | 0.129* | |
C31 | 0.7676 (11) | 0.4539 (5) | 0.5335 (4) | 0.092 (6)* | |
H31 | 0.6355 | 0.4837 | 0.5244 | 0.111* | |
C1 | 0.177 (2) | 0.2577 (10) | 0.3085 (6) | 0.064 (2)* | |
O2 | 0.3776 (18) | 0.6236 (8) | 0.4834 (5) | 0.086 (6) | |
C2 | 0.104 (2) | 0.3206 (11) | 0.2764 (7) | 0.064 (2)* | |
O3 | 0.689 (2) | 0.6127 (8) | 0.4459 (5) | 0.109 (7) | |
C3 | 0.165 (2) | 0.3060 (10) | 0.2342 (8) | 0.064 (2)* | |
H3 | 0.1079 | 0.3474 | 0.2131 | 0.077* | |
C4 | 0.313 (2) | 0.2282 (11) | 0.2246 (9) | 0.064 (2)* | |
C5 | 0.387 (2) | 0.1663 (11) | 0.2580 (7) | 0.064 (2)* | |
H5 | 0.4834 | 0.1137 | 0.2515 | 0.077* | |
C6 | 0.327 (2) | 0.1776 (10) | 0.2992 (6) | 0.064 (2)* | |
C14 | 0.495 (3) | 0.5849 (13) | 0.4546 (8) | 0.076 (6)* | |
C18 | 0.370 (3) | 0.2022 (13) | 0.1814 (9) | 0.087 (6)* | |
H18 | 0.3577 | 0.1286 | 0.1792 | 0.104* | |
C19 | 0.616 (3) | 0.2291 (13) | 0.1724 (9) | 0.110 (7)* | |
H19A | 0.6521 | 0.2117 | 0.1440 | 0.165* | |
H19B | 0.6384 | 0.3001 | 0.1766 | 0.165* | |
H19C | 0.7112 | 0.1921 | 0.1912 | 0.165* | |
C20 | 0.220 (3) | 0.2460 (15) | 0.1475 (10) | 0.134 (9)* | |
H20A | 0.2716 | 0.2244 | 0.1204 | 0.201* | |
H20B | 0.0694 | 0.2230 | 0.1517 | 0.201* | |
H20C | 0.2238 | 0.3183 | 0.1489 | 0.201* | |
O1 | −0.060 (4) | 0.2216 (16) | 0.3673 (8) | 0.084 (9) | 0.633 (4) |
C7 | 0.100 (4) | 0.2691 (19) | 0.3537 (7) | 0.090 (10)* | 0.633 (4) |
C8 | 0.2035 (18) | 0.3460 (8) | 0.3813 (4) | 0.054 (5)* | 0.633 (4) |
C9 | 0.0955 (15) | 0.3816 (8) | 0.4146 (5) | 0.073 (3)* | 0.633 (4) |
H9 | −0.0452 | 0.3565 | 0.4212 | 0.087* | 0.633 (4) |
C10 | 0.190 (2) | 0.4558 (9) | 0.4395 (4) | 0.073 (3)* | 0.633 (4) |
H10 | 0.1153 | 0.4783 | 0.4634 | 0.087* | 0.633 (4) |
C11 | 0.395 (2) | 0.4964 (9) | 0.4289 (5) | 0.068 (6)* | 0.633 (4) |
C12 | 0.5090 (16) | 0.4605 (9) | 0.3942 (5) | 0.073 (3)* | 0.633 (4) |
H12 | 0.6488 | 0.4864 | 0.3875 | 0.087* | 0.633 (4) |
C13 | 0.4146 (19) | 0.3857 (9) | 0.3693 (4) | 0.073 (3)* | 0.633 (4) |
H13 | 0.4876 | 0.3622 | 0.3455 | 0.087* | 0.633 (4) |
C15 | −0.054 (3) | 0.4104 (12) | 0.2900 (9) | 0.079 (6) | 0.633 (4) |
H15 | −0.0784 | 0.4057 | 0.3203 | 0.095* | 0.633 (4) |
C16 | −0.281 (3) | 0.4031 (13) | 0.2679 (9) | 0.073 (6)* | 0.633 (4) |
H16A | −0.3488 | 0.3394 | 0.2744 | 0.109* | 0.633 (4) |
H16B | −0.3756 | 0.4568 | 0.2774 | 0.109* | 0.633 (4) |
H16C | −0.2600 | 0.4084 | 0.2381 | 0.109* | 0.633 (4) |
C17 | 0.064 (3) | 0.5106 (12) | 0.2808 (10) | 0.079 (7)* | 0.633 (4) |
H17A | 0.2050 | 0.5123 | 0.2951 | 0.119* | 0.633 (4) |
H17B | 0.0879 | 0.5170 | 0.2511 | 0.119* | 0.633 (4) |
H17C | −0.0277 | 0.5654 | 0.2904 | 0.119* | 0.633 (4) |
C21 | 0.403 (4) | 0.1060 (16) | 0.3338 (9) | 0.081 (7) | 0.633 (4) |
H21 | 0.4263 | 0.1467 | 0.3592 | 0.097* | 0.633 (4) |
C22 | 0.221 (4) | 0.0286 (17) | 0.3440 (12) | 0.109 (9)* | 0.633 (4) |
H22A | 0.0832 | 0.0630 | 0.3498 | 0.164* | 0.633 (4) |
H22B | 0.2006 | −0.0156 | 0.3204 | 0.164* | 0.633 (4) |
H22C | 0.2645 | −0.0102 | 0.3681 | 0.164* | 0.633 (4) |
C23 | 0.622 (4) | 0.0524 (16) | 0.3245 (11) | 0.095 (9)* | 0.633 (4) |
H23A | 0.6589 | 0.0089 | 0.3476 | 0.142* | 0.633 (4) |
H23B | 0.6060 | 0.0130 | 0.2994 | 0.142* | 0.633 (4) |
H23C | 0.7379 | 0.1014 | 0.3208 | 0.142* | 0.633 (4) |
O1D | −0.132 (6) | 0.259 (4) | 0.358 (2) | 0.08 (2)* | 0.253 (4) |
C7D | 0.110 (6) | 0.256 (2) | 0.3561 (9) | 0.084 (18)* | 0.253 (4) |
C8D | 0.2035 (18) | 0.3460 (8) | 0.3813 (4) | 0.054 (5)* | 0.253 (4) |
C9D | 0.0955 (15) | 0.3816 (8) | 0.4146 (5) | 0.073 (3)* | 0.253 (4) |
H9D | −0.0452 | 0.3565 | 0.4212 | 0.087* | 0.253 (4) |
C10D | 0.190 (2) | 0.4558 (9) | 0.4395 (4) | 0.073 (3)* | 0.253 (4) |
H10D | 0.1153 | 0.4783 | 0.4634 | 0.087* | 0.253 (4) |
C11D | 0.395 (2) | 0.4964 (9) | 0.4289 (5) | 0.068 (6)* | 0.253 (4) |
C12D | 0.5090 (16) | 0.4605 (9) | 0.3942 (5) | 0.073 (3)* | 0.253 (4) |
H12D | 0.6488 | 0.4864 | 0.3875 | 0.087* | 0.253 (4) |
C13D | 0.4146 (19) | 0.3857 (9) | 0.3693 (4) | 0.073 (3)* | 0.253 (4) |
H13D | 0.4876 | 0.3622 | 0.3455 | 0.087* | 0.253 (4) |
C15D | −0.054 (3) | 0.4104 (12) | 0.2900 (9) | 0.079 (6) | 0.253 (4) |
H15D | −0.0784 | 0.4057 | 0.3203 | 0.095* | 0.253 (4) |
C16D | −0.281 (3) | 0.4031 (13) | 0.2679 (9) | 0.073 (6)* | 0.253 (4) |
H16D | −0.3488 | 0.3394 | 0.2744 | 0.109* | 0.253 (4) |
H16E | −0.3756 | 0.4568 | 0.2774 | 0.109* | 0.253 (4) |
H16F | −0.2600 | 0.4084 | 0.2381 | 0.109* | 0.253 (4) |
C17D | 0.064 (3) | 0.5106 (12) | 0.2808 (10) | 0.079 (7)* | 0.253 (4) |
H17D | 0.2050 | 0.5123 | 0.2951 | 0.119* | 0.253 (4) |
H17E | 0.0879 | 0.5170 | 0.2511 | 0.119* | 0.253 (4) |
H17F | −0.0277 | 0.5654 | 0.2904 | 0.119* | 0.253 (4) |
C21D | 0.401 (10) | 0.126 (4) | 0.3398 (11) | 0.084 (11)* | 0.253 (4) |
H21D | 0.5309 | 0.1647 | 0.3496 | 0.101* | 0.253 (4) |
C22D | 0.212 (9) | 0.155 (3) | 0.3693 (15) | 0.11 (2)* | 0.253 (4) |
H22D | 0.2683 | 0.1596 | 0.3978 | 0.127* | 0.253 (4) |
H22E | 0.0978 | 0.1028 | 0.3687 | 0.127* | 0.253 (4) |
C23D | 0.481 (12) | 0.021 (4) | 0.334 (2) | 0.10 (2)* | 0.253 (4) |
H23D | 0.6011 | 0.0202 | 0.3142 | 0.145* | 0.253 (4) |
H23E | 0.5334 | −0.0047 | 0.3606 | 0.145* | 0.253 (4) |
H23F | 0.3608 | −0.0202 | 0.3241 | 0.145* | 0.253 (4) |
O1P | −0.126 (12) | 0.266 (7) | 0.363 (2) | 0.09 (3)* | 0.114 (4) |
C7P | 0.039 (6) | 0.315 (3) | 0.3399 (11) | 0.08 (2)* | 0.114 (4) |
C8P | 0.155 (8) | 0.387 (2) | 0.3708 (11) | 0.060 (19)* | 0.114 (4) |
C9P | 0.050 (7) | 0.425 (4) | 0.4039 (15) | 0.070 (10)* | 0.114 (4) |
H9P | −0.0984 | 0.4077 | 0.4088 | 0.084* | 0.114 (4) |
C10P | 0.159 (8) | 0.489 (6) | 0.4314 (19) | 0.070 (10)* | 0.114 (4) |
H10P | 0.0860 | 0.5127 | 0.4551 | 0.084* | 0.114 (4) |
C11P | 0.378 (9) | 0.517 (7) | 0.423 (2) | 0.071 (19)* | 0.114 (4) |
C12P | 0.489 (8) | 0.479 (6) | 0.389 (2) | 0.070 (10)* | 0.114 (4) |
H12P | 0.6370 | 0.4963 | 0.3841 | 0.084* | 0.114 (4) |
C13P | 0.380 (8) | 0.414 (5) | 0.3615 (15) | 0.070 (10)* | 0.114 (4) |
H13P | 0.4512 | 0.3890 | 0.3378 | 0.084* | 0.114 (4) |
C15P | −0.037 (8) | 0.392 (3) | 0.3015 (14) | 0.079 (12)* | 0.114 (4) |
C16P | −0.284 (9) | 0.398 (8) | 0.294 (3) | 0.07 (3)* | 0.114 (4) |
H16G | −0.3484 | 0.4474 | 0.3126 | 0.100* | 0.114 (4) |
H16H | −0.3118 | 0.4177 | 0.2654 | 0.100* | 0.114 (4) |
H16I | −0.3510 | 0.3336 | 0.2992 | 0.100* | 0.114 (4) |
C17P | 0.067 (17) | 0.497 (3) | 0.304 (3) | 0.07 (3)* | 0.114 (4) |
H17G | −0.0277 | 0.5404 | 0.3202 | 0.101* | 0.114 (4) |
H17H | 0.2112 | 0.4926 | 0.3171 | 0.101* | 0.114 (4) |
H17I | 0.0833 | 0.5240 | 0.2761 | 0.101* | 0.114 (4) |
C21P | 0.403 (4) | 0.1060 (16) | 0.3338 (9) | 0.081 (7) | 0.114 (4) |
H21P | 0.4263 | 0.1467 | 0.3592 | 0.097* | 0.114 (4) |
C22P | 0.221 (4) | 0.0286 (17) | 0.3440 (12) | 0.109 (9)* | 0.114 (4) |
H22F | 0.0832 | 0.0630 | 0.3498 | 0.164* | 0.114 (4) |
H22G | 0.2006 | −0.0156 | 0.3204 | 0.164* | 0.114 (4) |
H22H | 0.2645 | −0.0102 | 0.3681 | 0.164* | 0.114 (4) |
C23P | 0.622 (4) | 0.0524 (16) | 0.3245 (11) | 0.095 (9)* | 0.114 (4) |
H23G | 0.6589 | 0.0089 | 0.3476 | 0.142* | 0.114 (4) |
H23H | 0.6060 | 0.0130 | 0.2994 | 0.142* | 0.114 (4) |
H23I | 0.7379 | 0.1014 | 0.3208 | 0.142* | 0.114 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.087 (8) | 0.081 (9) | 0.09 (2) | −0.001 (6) | 0.005 (10) | −0.012 (7) |
O3 | 0.092 (8) | 0.110 (10) | 0.13 (2) | −0.024 (8) | −0.001 (10) | −0.022 (9) |
O1 | 0.125 (16) | 0.095 (17) | 0.03 (2) | −0.020 (15) | 0.032 (16) | −0.026 (13) |
C15 | 0.076 (10) | 0.068 (10) | 0.093 (16) | 0.009 (9) | −0.009 (11) | 0.003 (10) |
C21 | 0.093 (12) | 0.073 (12) | 0.075 (16) | 0.020 (11) | 0.011 (13) | 0.011 (11) |
C15D | 0.076 (10) | 0.068 (10) | 0.093 (16) | 0.009 (9) | −0.009 (11) | 0.003 (10) |
C21P | 0.093 (12) | 0.073 (12) | 0.075 (16) | 0.020 (11) | 0.011 (13) | 0.011 (11) |
C26—C27 | 1.3765 | C8—C13 | 1.4209 |
C26—C31 | 1.3784 | C9—C10 | 1.3841 |
C26—C25 | 1.5095 | C10—C11 | 1.3855 |
N1—C25 | 1.5014 | C11—C12 | 1.3815 |
C24—C25 | 1.5074 | C12—C13 | 1.3894 |
C27—C28 | 1.3861 | C15—C17 | 1.53 (2) |
C28—C29 | 1.3484 | C15—C16 | 1.53 (2) |
C29—C30 | 1.3675 | C21—C23 | 1.52 (2) |
C30—C31 | 1.3909 | C21—C22 | 1.53 (2) |
C1—C2 | 1.39 (2) | O1D—C7D | 1.45 (3) |
C1—C6 | 1.422 (17) | C7D—C22D | 1.53 (3) |
C1—C7P | 1.50 (2) | C7D—C8D | 1.54 (2) |
C1—C7 | 1.52 (2) | C8D—C9D | 1.3283 |
C1—C7D | 1.57 (2) | C8D—C13D | 1.4209 |
O2—C14 | 1.26 (2) | C9D—C10D | 1.3841 |
C2—C3 | 1.41 (3) | C10D—C11D | 1.3855 |
C2—C15P | 1.50 (2) | C11D—C12D | 1.3815 |
C2—C15 | 1.58 (2) | C12D—C13D | 1.3894 |
C2—C15D | 1.58 (2) | C15D—C17D | 1.53 (2) |
O3—C14 | 1.250 (19) | C15D—C16D | 1.53 (2) |
C3—C4 | 1.395 (18) | C21D—C23D | 1.49 (3) |
C4—C5 | 1.41 (3) | C21D—C22D | 1.52 (3) |
C4—C18 | 1.46 (3) | O1P—C7P | 1.40 (3) |
C5—C6 | 1.37 (3) | C7P—C8P | 1.53 (2) |
C6—C21P | 1.53 (2) | C7P—C15P | 1.66 (2) |
C6—C21 | 1.53 (2) | C8P—C9P | 1.3283 |
C6—C21D | 1.53 (2) | C8P—C13P | 1.4209 |
C14—C11P | 1.51 (2) | C9P—C10P | 1.3841 |
C14—C11 | 1.55 (2) | C10P—C11P | 1.3855 |
C14—C11D | 1.55 (2) | C11P—C12P | 1.3815 |
C18—C20 | 1.52 (3) | C12P—C13P | 1.3894 |
C18—C19 | 1.54 (2) | C15P—C16P | 1.50 (3) |
O1—C7 | 1.226 (19) | C15P—C17P | 1.53 (3) |
C7—C8 | 1.482 (19) | C21P—C23P | 1.52 (2) |
C8—C9 | 1.3283 | C21P—C22P | 1.53 (2) |
C27—C26—C31 | 118.2 | C10—C11—C14 | 120.4 (13) |
C27—C26—C25 | 120.5 | C11—C12—C13 | 120.1 |
C31—C26—C25 | 121.3 | C12—C13—C8 | 118.2 |
N1—C25—C24 | 109.2 | C17—C15—C16 | 112.0 (17) |
N1—C25—C26 | 109.8 | C17—C15—C2 | 109.1 (14) |
C24—C25—C26 | 115.2 | C16—C15—C2 | 110.9 (16) |
C26—C27—C28 | 120.9 | C23—C21—C6 | 114 (2) |
C29—C28—C27 | 120.2 | C23—C21—C22 | 109.9 (16) |
C28—C29—C30 | 120.2 | C6—C21—C22 | 110.9 (19) |
C29—C30—C31 | 119.9 | O1D—C7D—C22D | 114 (3) |
C26—C31—C30 | 120.5 | O1D—C7D—C8D | 108 (3) |
C2—C1—C6 | 119.5 (16) | C22D—C7D—C8D | 113 (3) |
C2—C1—C7P | 90.6 (19) | O1D—C7D—C1 | 107 (3) |
C6—C1—C7P | 150 (2) | C22D—C7D—C1 | 100 (2) |
C2—C1—C7 | 122.8 (16) | C8D—C7D—C1 | 113.5 (19) |
C6—C1—C7 | 117.7 (17) | C9D—C8D—C13D | 121.1 |
C2—C1—C7D | 129.8 (19) | C9D—C8D—C7D | 120.9 (13) |
C6—C1—C7D | 110.6 (18) | C13D—C8D—C7D | 117.9 (13) |
C1—C2—C3 | 122.6 (16) | C8D—C9D—C10D | 120.7 |
C1—C2—C15P | 99 (2) | C9D—C10D—C11D | 119.9 |
C3—C2—C15P | 138 (2) | C12D—C11D—C10D | 119.9 |
C1—C2—C15 | 116.1 (18) | C12D—C11D—C14 | 119.6 (13) |
C3—C2—C15 | 121.4 (17) | C10D—C11D—C14 | 120.4 (13) |
C1—C2—C15D | 116.1 (18) | C11D—C12D—C13D | 120.1 |
C3—C2—C15D | 121.4 (17) | C12D—C13D—C8D | 118.2 |
C4—C3—C2 | 118 (2) | C17D—C15D—C16D | 112.0 (17) |
C3—C4—C5 | 118 (2) | C17D—C15D—C2 | 109.1 (14) |
C3—C4—C18 | 122 (2) | C16D—C15D—C2 | 110.9 (16) |
C5—C4—C18 | 120.1 (17) | C23D—C21D—C22D | 123 (4) |
C6—C5—C4 | 125.2 (18) | C23D—C21D—C6 | 114 (4) |
C5—C6—C1 | 116.6 (15) | C22D—C21D—C6 | 101 (3) |
C5—C6—C21P | 123.2 (16) | C21D—C22D—C7D | 110 (3) |
C1—C6—C21P | 120.1 (18) | O1P—C7P—C1 | 120 (4) |
C5—C6—C21 | 123.2 (16) | O1P—C7P—C8P | 106 (3) |
C1—C6—C21 | 120.1 (18) | C1—C7P—C8P | 119 (2) |
C5—C6—C21D | 133.5 (19) | O1P—C7P—C15P | 119 (4) |
C1—C6—C21D | 109.7 (19) | C1—C7P—C15P | 88.4 (18) |
O3—C14—O2 | 124.0 (19) | C8P—C7P—C15P | 103 (2) |
O3—C14—C11P | 117 (3) | C9P—C8P—C13P | 121.1 |
O2—C14—C11P | 117 (2) | C9P—C8P—C7P | 122 (2) |
O3—C14—C11 | 118 (2) | C13P—C8P—C7P | 117 (2) |
O2—C14—C11 | 118.5 (17) | C8P—C9P—C10P | 120.75 (8) |
O3—C14—C11D | 118 (2) | C9P—C10P—C11P | 119.9 |
O2—C14—C11D | 118.5 (17) | C12P—C11P—C10P | 119.88 (5) |
C4—C18—C20 | 116.3 (18) | C12P—C11P—C14 | 121 (3) |
C4—C18—C19 | 110 (2) | C10P—C11P—C14 | 119 (3) |
C20—C18—C19 | 110 (2) | C11P—C12P—C13P | 120.14 (8) |
O1—C7—C8 | 118 (2) | C12P—C13P—C8P | 118.2 |
O1—C7—C1 | 121.4 (19) | C2—C15P—C16P | 120 (4) |
C8—C7—C1 | 120.1 (16) | C2—C15P—C17P | 112 (4) |
C9—C8—C13 | 121.1 | C16P—C15P—C17P | 111 (3) |
C9—C8—C7 | 120.8 (12) | C2—C15P—C7P | 81.4 (18) |
C13—C8—C7 | 117.9 (12) | C16P—C15P—C7P | 115 (4) |
C8—C9—C10 | 120.7 | C17P—C15P—C7P | 114 (4) |
C9—C10—C11 | 119.9 | C23P—C21P—C6 | 114 (2) |
C12—C11—C10 | 119.9 | C23P—C21P—C22P | 109.9 (16) |
C12—C11—C14 | 119.6 (13) | C6—C21P—C22P | 110.9 (19) |
C31H39NO3 | Dx = 1.244 Mg m−3 |
Mr = 473.63 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 453 reflections |
a = 5.997 (2) Å | θ = 5.7–22.7° |
b = 13.267 (7) Å | µ = 0.08 mm−1 |
c = 31.79 (5) Å | T = 299 K |
V = 2529 (4) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.10 × 0.08 mm |
F(000) = 1024 |
KM4 with Eos CCD diffractometer | 2189 independent reflections |
Radiation source: fine-focus sealed tube | 653 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.186 |
Detector resolution: 15.9718 pixels mm-1 | θmax = 24.5°, θmin = 5.6° |
φ– and ω scans | h = −6→6 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −14→11 |
Tmin = 0.324, Tmax = 1.000 | l = −22→20 |
5382 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.099 | w = 1/[σ2(Fo2) + (0.0778P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.284 | (Δ/σ)max < 0.001 |
S = 0.97 | Δρmax = 0.13 e Å−3 |
2189 reflections | Δρmin = −0.13 e Å−3 |
164 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
154 restraints | Absolute structure parameter: −6.7 (10) |
Primary atom site location: isomorphous structure methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O2 | 0.3784 (19) | 0.6239 (9) | 0.4829 (6) | 0.102 (7) | |
O3 | 0.687 (2) | 0.6141 (9) | 0.4456 (6) | 0.120 (8) | |
C6 | 0.3263 (18) | 0.1785 (7) | 0.2991 (4) | 0.069 (5)* | |
C1 | 0.1776 (18) | 0.2580 (8) | 0.3074 (4) | 0.075 (3)* | |
C2 | 0.0986 (14) | 0.3213 (6) | 0.2758 (5) | 0.075 (3)* | |
C3 | 0.1683 (17) | 0.3033 (7) | 0.2348 (4) | 0.075 (3)* | |
H3 | 0.1141 | 0.3443 | 0.2134 | 0.090* | |
C4 | 0.3133 (18) | 0.2276 (8) | 0.2247 (4) | 0.075 (3)* | |
C5 | 0.3912 (13) | 0.1657 (6) | 0.2574 (5) | 0.075 (3)* | |
H5 | 0.4902 | 0.1140 | 0.2509 | 0.090* | |
C14 | 0.499 (4) | 0.5840 (14) | 0.4550 (9) | 0.088 (7)* | |
C18 | 0.371 (3) | 0.2031 (14) | 0.1800 (9) | 0.095 (6)* | |
H18 | 0.3586 | 0.1296 | 0.1776 | 0.115* | |
C19 | 0.617 (3) | 0.2280 (14) | 0.1723 (9) | 0.128 (8)* | |
H19A | 0.6547 | 0.2124 | 0.1437 | 0.192* | |
H19B | 0.6419 | 0.2984 | 0.1774 | 0.192* | |
H19C | 0.7083 | 0.1889 | 0.1909 | 0.192* | |
C20 | 0.218 (3) | 0.2463 (15) | 0.1468 (10) | 0.132 (8)* | |
H20A | 0.2687 | 0.2263 | 0.1195 | 0.197* | |
H20B | 0.0690 | 0.2215 | 0.1512 | 0.197* | |
H20C | 0.2177 | 0.3185 | 0.1488 | 0.197* | |
C26 | 0.9376 (10) | 0.5132 (5) | 0.5487 (4) | 0.088 (6)* | |
N1 | 0.9533 (16) | 0.6725 (6) | 0.5090 (5) | 0.098 (5)* | |
H1A | 0.8500 | 0.6507 | 0.4911 | 0.118* | |
H1B | 1.0878 | 0.6549 | 0.4998 | 0.118* | |
H1C | 0.9454 | 0.7393 | 0.5111 | 0.118* | |
C24 | 0.6941 (19) | 0.6632 (7) | 0.5686 (5) | 0.104 (7)* | |
H24A | 0.5765 | 0.6449 | 0.5496 | 0.156* | |
H24B | 0.6986 | 0.7351 | 0.5716 | 0.156* | |
H24C | 0.6672 | 0.6329 | 0.5956 | 0.156* | |
C25 | 0.9139 (13) | 0.6263 (5) | 0.5515 (4) | 0.114 (7)* | |
H25 | 1.0313 | 0.6510 | 0.5703 | 0.137* | |
C27 | 1.1310 (13) | 0.4667 (6) | 0.5617 (5) | 0.107 (7)* | |
H27 | 1.2488 | 0.5056 | 0.5716 | 0.128* | |
C28 | 1.1527 (17) | 0.3628 (7) | 0.5601 (6) | 0.120 (7)* | |
H28 | 1.2840 | 0.3325 | 0.5691 | 0.143* | |
C29 | 0.984 (2) | 0.3055 (5) | 0.5453 (6) | 0.121 (8)* | |
H29 | 0.9999 | 0.2358 | 0.5442 | 0.145* | |
C30 | 0.7901 (18) | 0.3495 (5) | 0.5322 (6) | 0.114 (7)* | |
H30 | 0.6738 | 0.3097 | 0.5223 | 0.137* | |
C31 | 0.7669 (12) | 0.4537 (5) | 0.5337 (5) | 0.106 (7)* | |
H31 | 0.6353 | 0.4835 | 0.5245 | 0.127* | |
O1 | −0.058 (4) | 0.2222 (17) | 0.3674 (9) | 0.102 (11) | 0.595 (4) |
C7 | 0.099 (5) | 0.271 (2) | 0.3529 (7) | 0.113 (12)* | 0.595 (4) |
C8 | 0.206 (2) | 0.3452 (8) | 0.3817 (5) | 0.067 (6)* | 0.595 (4) |
C9 | 0.0969 (17) | 0.3811 (9) | 0.4148 (5) | 0.085 (4)* | 0.595 (4) |
H9 | −0.0426 | 0.3552 | 0.4216 | 0.102* | 0.595 (4) |
C10 | 0.188 (2) | 0.4568 (11) | 0.4394 (4) | 0.085 (4)* | 0.595 (4) |
H10 | 0.1133 | 0.4795 | 0.4631 | 0.102* | 0.595 (4) |
C11 | 0.392 (3) | 0.4985 (12) | 0.4284 (6) | 0.083 (7)* | 0.595 (4) |
C12 | 0.507 (2) | 0.4622 (12) | 0.3939 (6) | 0.085 (4)* | 0.595 (4) |
H12 | 0.6453 | 0.4890 | 0.3870 | 0.102* | 0.595 (4) |
C13 | 0.415 (2) | 0.3860 (11) | 0.3694 (4) | 0.085 (4)* | 0.595 (4) |
H13 | 0.4888 | 0.3622 | 0.3457 | 0.102* | 0.595 (4) |
C15 | −0.051 (3) | 0.4115 (12) | 0.2897 (9) | 0.084 (7) | 0.595 (4) |
H15 | −0.0756 | 0.4065 | 0.3200 | 0.101* | 0.595 (4) |
C16 | −0.276 (3) | 0.4035 (14) | 0.2676 (11) | 0.088 (5)* | 0.595 (4) |
H16A | −0.3438 | 0.3399 | 0.2743 | 0.132* | 0.595 (4) |
H16B | −0.3713 | 0.4572 | 0.2769 | 0.132* | 0.595 (4) |
H16C | −0.2552 | 0.4083 | 0.2377 | 0.132* | 0.595 (4) |
C17 | 0.069 (3) | 0.5110 (13) | 0.2807 (11) | 0.088 (5)* | 0.595 (4) |
H17A | 0.2096 | 0.5119 | 0.2953 | 0.132* | 0.595 (4) |
H17B | 0.0951 | 0.5173 | 0.2510 | 0.132* | 0.595 (4) |
H17C | −0.0210 | 0.5662 | 0.2902 | 0.132* | 0.595 (4) |
C21 | 0.401 (4) | 0.1067 (19) | 0.3335 (9) | 0.097 (7) | 0.595 (4) |
H21 | 0.4222 | 0.1459 | 0.3593 | 0.117* | 0.595 (4) |
C22 | 0.222 (4) | 0.0273 (18) | 0.3420 (12) | 0.108 (8)* | 0.595 (4) |
H22A | 0.2726 | −0.0173 | 0.3638 | 0.161* | 0.595 (4) |
H22B | 0.0872 | 0.0599 | 0.3507 | 0.161* | 0.595 (4) |
H22C | 0.1952 | −0.0105 | 0.3168 | 0.161* | 0.595 (4) |
C23 | 0.620 (4) | 0.0531 (18) | 0.3236 (12) | 0.108 (8)* | 0.595 (4) |
H23A | 0.6578 | 0.0090 | 0.3464 | 0.161* | 0.595 (4) |
H23B | 0.6030 | 0.0145 | 0.2983 | 0.161* | 0.595 (4) |
H23C | 0.7357 | 0.1021 | 0.3199 | 0.161* | 0.595 (4) |
O1D | −0.134 (6) | 0.265 (4) | 0.3577 (19) | 0.11 (2)* | 0.285 (4) |
C7D | 0.109 (6) | 0.258 (2) | 0.3552 (8) | 0.109 (18)* | 0.285 (4) |
C8D | 0.206 (2) | 0.3452 (8) | 0.3817 (5) | 0.067 (6)* | 0.285 (4) |
C9D | 0.0969 (17) | 0.3811 (9) | 0.4148 (5) | 0.085 (4)* | 0.285 (4) |
H9D | −0.0426 | 0.3552 | 0.4216 | 0.102* | 0.285 (4) |
C10D | 0.188 (2) | 0.4568 (11) | 0.4394 (4) | 0.085 (4)* | 0.285 (4) |
H10D | 0.1133 | 0.4795 | 0.4631 | 0.102* | 0.285 (4) |
C11D | 0.392 (3) | 0.4985 (12) | 0.4284 (6) | 0.083 (7)* | 0.285 (4) |
C12D | 0.507 (2) | 0.4622 (12) | 0.3939 (6) | 0.085 (4)* | 0.285 (4) |
H12D | 0.6453 | 0.4890 | 0.3870 | 0.102* | 0.285 (4) |
C13D | 0.415 (2) | 0.3860 (11) | 0.3694 (4) | 0.085 (4)* | 0.285 (4) |
H13D | 0.4888 | 0.3622 | 0.3457 | 0.102* | 0.285 (4) |
C15D | −0.051 (3) | 0.4115 (12) | 0.2897 (9) | 0.084 (7) | 0.285 (4) |
H15D | −0.0756 | 0.4065 | 0.3200 | 0.101* | 0.285 (4) |
C16D | −0.276 (3) | 0.4035 (14) | 0.2676 (11) | 0.088 (5)* | 0.285 (4) |
H16D | −0.3438 | 0.3399 | 0.2743 | 0.132* | 0.285 (4) |
H16E | −0.3713 | 0.4572 | 0.2769 | 0.132* | 0.285 (4) |
H16F | −0.2552 | 0.4083 | 0.2377 | 0.132* | 0.285 (4) |
C17D | 0.069 (3) | 0.5110 (13) | 0.2807 (11) | 0.088 (5)* | 0.285 (4) |
H17D | 0.2096 | 0.5119 | 0.2953 | 0.132* | 0.285 (4) |
H17E | 0.0951 | 0.5173 | 0.2510 | 0.132* | 0.285 (4) |
H17F | −0.0210 | 0.5662 | 0.2902 | 0.132* | 0.285 (4) |
C21D | 0.394 (9) | 0.126 (4) | 0.3397 (11) | 0.098 (11)* | 0.285 (4) |
H21D | 0.5172 | 0.1663 | 0.3507 | 0.118* | 0.285 (4) |
C22D | 0.197 (10) | 0.153 (3) | 0.3672 (16) | 0.16 (3)* | 0.285 (4) |
H22D | 0.2418 | 0.1532 | 0.3965 | 0.188* | 0.285 (4) |
H22E | 0.0792 | 0.1037 | 0.3637 | 0.188* | 0.285 (4) |
C23D | 0.493 (12) | 0.025 (4) | 0.332 (2) | 0.12 (2)* | 0.285 (4) |
H23D | 0.6163 | 0.0303 | 0.3134 | 0.174* | 0.285 (4) |
H23E | 0.5435 | −0.0027 | 0.3588 | 0.174* | 0.285 (4) |
H23F | 0.3822 | −0.0194 | 0.3206 | 0.174* | 0.285 (4) |
O1P | −0.110 (13) | 0.258 (6) | 0.365 (2) | 0.11 (3)* | 0.121 (4) |
C7P | 0.042 (6) | 0.313 (3) | 0.3402 (11) | 0.11 (2)* | 0.121 (4) |
C8P | 0.159 (8) | 0.385 (2) | 0.3710 (11) | 0.075 (19)* | 0.121 (4) |
C9P | 0.055 (8) | 0.420 (4) | 0.4048 (15) | 0.082 (10)* | 0.121 (4) |
H9P | −0.0935 | 0.4037 | 0.4095 | 0.098* | 0.121 (4) |
C10P | 0.165 (10) | 0.482 (7) | 0.4331 (19) | 0.082 (10)* | 0.121 (4) |
H10P | 0.0930 | 0.5042 | 0.4572 | 0.098* | 0.121 (4) |
C11P | 0.384 (11) | 0.510 (8) | 0.425 (2) | 0.079 (19)* | 0.121 (4) |
C12P | 0.494 (10) | 0.474 (7) | 0.390 (2) | 0.082 (10)* | 0.121 (4) |
H12P | 0.6418 | 0.4916 | 0.3856 | 0.098* | 0.121 (4) |
C13P | 0.383 (9) | 0.412 (5) | 0.3620 (16) | 0.082 (10)* | 0.121 (4) |
H13P | 0.4538 | 0.3887 | 0.3379 | 0.098* | 0.121 (4) |
C15P | −0.048 (8) | 0.387 (4) | 0.3022 (13) | 0.085 (13)* | 0.121 (4) |
C16P | −0.295 (8) | 0.384 (8) | 0.294 (3) | 0.11 (3)* | 0.121 (4) |
H16G | −0.3702 | 0.4290 | 0.3127 | 0.166* | 0.121 (4) |
H16H | −0.3232 | 0.4038 | 0.2653 | 0.166* | 0.121 (4) |
H16I | −0.3490 | 0.3165 | 0.2981 | 0.166* | 0.121 (4) |
C17P | 0.036 (17) | 0.495 (3) | 0.306 (3) | 0.05 (3)* | 0.121 (4) |
H17G | −0.0657 | 0.5331 | 0.3234 | 0.082* | 0.121 (4) |
H17H | 0.1806 | 0.4950 | 0.3190 | 0.082* | 0.121 (4) |
H17I | 0.0444 | 0.5252 | 0.2788 | 0.082* | 0.121 (4) |
C21P | 0.401 (4) | 0.1067 (19) | 0.3335 (9) | 0.097 (7) | 0.121 (4) |
H21P | 0.4222 | 0.1459 | 0.3593 | 0.117* | 0.121 (4) |
C22P | 0.222 (4) | 0.0273 (18) | 0.3420 (12) | 0.108 (8)* | 0.121 (4) |
H22F | 0.2726 | −0.0173 | 0.3638 | 0.161* | 0.121 (4) |
H22G | 0.0872 | 0.0599 | 0.3507 | 0.161* | 0.121 (4) |
H22H | 0.1952 | −0.0105 | 0.3168 | 0.161* | 0.121 (4) |
C23P | 0.620 (4) | 0.0531 (18) | 0.3236 (12) | 0.108 (8)* | 0.121 (4) |
H23G | 0.6578 | 0.0090 | 0.3464 | 0.161* | 0.121 (4) |
H23H | 0.6030 | 0.0145 | 0.2983 | 0.161* | 0.121 (4) |
H23I | 0.7357 | 0.1021 | 0.3199 | 0.161* | 0.121 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.096 (8) | 0.088 (10) | 0.12 (2) | 0.001 (7) | 0.021 (11) | −0.020 (8) |
O3 | 0.092 (8) | 0.137 (12) | 0.13 (3) | −0.028 (8) | 0.019 (11) | −0.004 (10) |
O1 | 0.140 (18) | 0.084 (17) | 0.08 (3) | −0.007 (16) | 0.030 (18) | −0.021 (15) |
C15 | 0.101 (11) | 0.063 (10) | 0.088 (16) | 0.006 (9) | −0.014 (12) | −0.010 (10) |
C21 | 0.097 (12) | 0.098 (13) | 0.098 (16) | 0.032 (12) | 0.021 (13) | 0.012 (12) |
C15D | 0.101 (11) | 0.063 (10) | 0.088 (16) | 0.006 (9) | −0.014 (12) | −0.010 (10) |
C21P | 0.097 (12) | 0.098 (13) | 0.098 (16) | 0.032 (12) | 0.021 (13) | 0.012 (12) |
O2—C14 | 1.26 (3) | C8—C13 | 1.4209 |
O3—C14 | 1.23 (2) | C9—C10 | 1.3841 |
C6—C5 | 1.3947 | C10—C11 | 1.3855 |
C6—C1 | 1.4060 | C11—C12 | 1.3814 |
C6—C21P | 1.517 (19) | C12—C13 | 1.3894 |
C6—C21 | 1.517 (19) | C15—C16 | 1.53 (3) |
C6—C21D | 1.52 (2) | C15—C17 | 1.53 (2) |
C1—C2 | 1.3900 | C21—C23 | 1.52 (2) |
C1—C7P | 1.51 (2) | C21—C22 | 1.53 (2) |
C1—C7 | 1.53 (2) | O1D—C7D | 1.46 (2) |
C1—C7D | 1.58 (2) | C7D—C22D | 1.53 (3) |
C2—C3 | 1.3901 | C7D—C8D | 1.55 (2) |
C2—C15P | 1.50 (2) | C8D—C9D | 1.3283 |
C2—C15 | 1.558 (19) | C8D—C13D | 1.4209 |
C2—C15D | 1.558 (19) | C9D—C10D | 1.3841 |
C3—C4 | 1.3667 | C10D—C11D | 1.3855 |
C4—C5 | 1.4051 | C11D—C12D | 1.3814 |
C4—C18 | 1.50 (3) | C12D—C13D | 1.3894 |
C14—C11P | 1.52 (2) | C15D—C16D | 1.53 (3) |
C14—C11 | 1.55 (2) | C15D—C17D | 1.53 (2) |
C14—C11D | 1.55 (2) | C21D—C23D | 1.49 (3) |
C18—C20 | 1.51 (3) | C21D—C22D | 1.52 (3) |
C18—C19 | 1.53 (2) | O1P—C7P | 1.40 (2) |
C26—C27 | 1.3765 | C7P—C8P | 1.53 (2) |
C26—C31 | 1.3784 | C7P—C15P | 1.65 (2) |
C26—C25 | 1.5095 | C8P—C9P | 1.3283 |
N1—C25 | 1.5015 | C8P—C13P | 1.4208 |
C24—C25 | 1.5074 | C9P—C10P | 1.3842 |
C27—C28 | 1.3862 | C10P—C11P | 1.3855 |
C28—C29 | 1.3487 | C11P—C12P | 1.3816 |
C29—C30 | 1.3677 | C12P—C13P | 1.3894 |
C30—C31 | 1.3909 | C15P—C16P | 1.50 (3) |
O1—C7 | 1.24 (2) | C15P—C17P | 1.52 (3) |
C7—C8 | 1.490 (19) | C21P—C23P | 1.52 (2) |
C8—C9 | 1.3283 | C21P—C22P | 1.53 (2) |
C5—C6—C1 | 116.5 | C10—C11—C14 | 121.4 (15) |
C5—C6—C21P | 121.8 (13) | C11—C12—C13 | 120.1 |
C1—C6—C21P | 121.7 (12) | C12—C13—C8 | 118.2 |
C5—C6—C21 | 121.8 (13) | C16—C15—C17 | 113.1 (18) |
C1—C6—C21 | 121.7 (12) | C16—C15—C2 | 109.1 (16) |
C5—C6—C21D | 132.5 (16) | C17—C15—C2 | 109.8 (14) |
C1—C6—C21D | 110.9 (16) | C6—C21—C23 | 113 (2) |
C2—C1—C6 | 122.4 | C6—C21—C22 | 111 (2) |
C2—C1—C7P | 91.3 (17) | C23—C21—C22 | 108.5 (18) |
C6—C1—C7P | 146.3 (17) | O1D—C7D—C22D | 113 (3) |
C2—C1—C7 | 120.6 (15) | O1D—C7D—C8D | 107 (3) |
C6—C1—C7 | 116.9 (15) | C22D—C7D—C8D | 114 (3) |
C2—C1—C7D | 127.3 (16) | O1D—C7D—C1 | 108 (3) |
C6—C1—C7D | 110.2 (16) | C22D—C7D—C1 | 99 (2) |
C1—C2—C3 | 118.0 | C8D—C7D—C1 | 115.2 (19) |
C1—C2—C15P | 98.6 (18) | C9D—C8D—C13D | 121.1 |
C3—C2—C15P | 143.4 (18) | C9D—C8D—C7D | 121.0 (14) |
C1—C2—C15 | 117.2 (14) | C13D—C8D—C7D | 117.9 (13) |
C3—C2—C15 | 124.7 (14) | C8D—C9D—C10D | 120.7 |
C1—C2—C15D | 117.2 (14) | C9D—C10D—C11D | 119.9 |
C3—C2—C15D | 124.7 (14) | C12D—C11D—C10D | 119.9 |
C4—C3—C2 | 122.6 | C12D—C11D—C14 | 118.7 (16) |
C3—C4—C5 | 117.8 | C10D—C11D—C14 | 121.4 (15) |
C3—C4—C18 | 122.1 (13) | C11D—C12D—C13D | 120.1 |
C5—C4—C18 | 119.8 (13) | C12D—C13D—C8D | 118.2 |
C6—C5—C4 | 122.7 | C16D—C15D—C17D | 113.1 (18) |
O3—C14—O2 | 124 (2) | C16D—C15D—C2 | 109.1 (16) |
O3—C14—C11P | 118 (3) | C17D—C15D—C2 | 109.8 (14) |
O2—C14—C11P | 116 (2) | C23D—C21D—C22D | 128 (4) |
O3—C14—C11 | 119 (2) | C23D—C21D—C6 | 113 (3) |
O2—C14—C11 | 116.8 (19) | C22D—C21D—C6 | 100 (3) |
O3—C14—C11D | 119 (2) | C21D—C22D—C7D | 110 (3) |
O2—C14—C11D | 116.8 (19) | O1P—C7P—C1 | 119 (4) |
C4—C18—C20 | 116.0 (17) | O1P—C7P—C8P | 105 (3) |
C4—C18—C19 | 109.2 (19) | C1—C7P—C8P | 120 (2) |
C20—C18—C19 | 113 (2) | O1P—C7P—C15P | 120 (4) |
C27—C26—C31 | 118.2 | C1—C7P—C15P | 87.6 (17) |
C27—C26—C25 | 120.5 | C8P—C7P—C15P | 104 (2) |
C31—C26—C25 | 121.3 | C9P—C8P—C13P | 121.06 (5) |
N1—C25—C24 | 109.2 | C9P—C8P—C7P | 121 (2) |
N1—C25—C26 | 109.8 | C13P—C8P—C7P | 117 (2) |
C24—C25—C26 | 115.2 | C8P—C9P—C10P | 120.75 (10) |
C26—C27—C28 | 120.9 | C9P—C10P—C11P | 119.9 |
C29—C28—C27 | 120.2 | C12P—C11P—C10P | 119.88 (5) |
C28—C29—C30 | 120.2 | C12P—C11P—C14 | 120 (3) |
C29—C30—C31 | 119.9 | C10P—C11P—C14 | 120 (3) |
C26—C31—C30 | 120.5 | C11P—C12P—C13P | 120.14 (11) |
O1—C7—C8 | 116 (2) | C12P—C13P—C8P | 118.2 |
O1—C7—C1 | 122 (2) | C2—C15P—C16P | 118 (4) |
C8—C7—C1 | 121.6 (17) | C2—C15P—C17P | 114 (4) |
C9—C8—C13 | 121.1 | C16P—C15P—C17P | 112 (3) |
C9—C8—C7 | 120.9 (13) | C2—C15P—C7P | 82.5 (17) |
C13—C8—C7 | 117.5 (12) | C16P—C15P—C7P | 116 (4) |
C8—C9—C10 | 120.7 | C17P—C15P—C7P | 113 (3) |
C9—C10—C11 | 119.9 | C6—C21P—C23P | 113 (2) |
C12—C11—C10 | 119.9 | C6—C21P—C22P | 111 (2) |
C12—C11—C14 | 118.7 (16) | C23P—C21P—C22P | 108.5 (18) |
C23H26.67O3·C8H12N | Dx = 1.243 Mg m−3 |
Mr = 473.63 | Synchrotron radiation, λ = 0.6889 Å |
Orthorhombic, P212121 | Cell parameters from 2230 reflections |
a = 5.9560 (5) Å | θ = 3.0–25.8° |
b = 13.3207 (11) Å | µ = 0.07 mm−1 |
c = 31.89 (3) Å | T = 295 K |
V = 2530 (2) Å3 | Block, colourless |
Z = 4 | 0.18 × 0.10 × 0.08 mm |
F(000) = 1024 |
Dectris-CrysAlisPro-abstract goniometer imported dectris images diffractometer | 1824 independent reflections |
Radiation source: synchrotron | 1070 reflections with I > 2σ(I) |
Synchrotron monochromator | Rint = 0.060 |
Detector resolution: 5.8140 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω and φ scans | h = −7→7 |
Absorption correction: multi-scan Scale3 AbsPack (Rigaku OD, 2015) | k = −16→16 |
Tmin = 0.600, Tmax = 1.000 | l = −10→11 |
8166 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.079 | w = 1/[σ2(Fo2) + (0.1888P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.256 | (Δ/σ)max = 0.002 |
S = 0.98 | Δρmax = 0.14 e Å−3 |
1824 reflections | Δρmin = −0.16 e Å−3 |
263 parameters | Absolute structure: The absolute configuration was assigned to agree with that of its precursor (S)-(-)-1-phenylethaneamine at the chiral centre C25. |
356 restraints | Absolute structure parameter: 1.1 (10) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O2 | 0.3828 (12) | 0.6234 (5) | 0.4826 (6) | 0.085 (13) | |
O3 | 0.6870 (13) | 0.6146 (6) | 0.4455 (7) | 0.133 (15) | |
C6 | 0.3211 (11) | 0.1811 (4) | 0.2994 (4) | 0.073 (8) | |
C1 | 0.1764 (11) | 0.2613 (5) | 0.3087 (4) | 0.071 (8) | |
C2 | 0.0984 (9) | 0.3271 (3) | 0.2780 (4) | 0.069 (8) | |
C3 | 0.1649 (10) | 0.3108 (4) | 0.2367 (4) | 0.072 (8) | |
H3 | 0.1113 | 0.3536 | 0.2158 | 0.086* | |
C4 | 0.3059 (12) | 0.2345 (5) | 0.2255 (4) | 0.073 (8) | |
C5 | 0.3831 (9) | 0.1701 (3) | 0.2573 (4) | 0.069 (8) | |
H5 | 0.4794 | 0.1180 | 0.2501 | 0.083* | |
C14 | 0.4974 (19) | 0.5864 (8) | 0.4544 (9) | 0.090 (3)* | |
C18 | 0.377 (2) | 0.2073 (9) | 0.1843 (11) | 0.103 (4)* | |
H18 | 0.3610 | 0.1343 | 0.1819 | 0.123* | |
C19 | 0.626 (2) | 0.2335 (9) | 0.1741 (11) | 0.115 (4)* | |
H19A | 0.6603 | 0.2129 | 0.1460 | 0.172* | |
H19B | 0.6480 | 0.3046 | 0.1767 | 0.172* | |
H19C | 0.7229 | 0.1990 | 0.1934 | 0.172* | |
C20 | 0.231 (3) | 0.2520 (11) | 0.1526 (16) | 0.149 (6)* | |
H20A | 0.2822 | 0.2326 | 0.1252 | 0.224* | |
H20B | 0.0801 | 0.2291 | 0.1567 | 0.224* | |
H20C | 0.2360 | 0.3238 | 0.1551 | 0.224* | |
C26 | 0.9435 (8) | 0.5141 (3) | 0.5492 (4) | 0.097 (3)* | |
N1 | 0.9570 (12) | 0.6719 (4) | 0.5084 (4) | 0.079 (14) | |
H1A | 0.8528 | 0.6494 | 0.4908 | 0.095* | |
H1B | 1.0910 | 0.6540 | 0.4990 | 0.095* | |
H1C | 0.9490 | 0.7388 | 0.5100 | 0.095* | |
C24 | 0.7006 (15) | 0.6647 (5) | 0.5685 (5) | 0.134 (5)* | |
H24A | 0.5821 | 0.6456 | 0.5498 | 0.201* | |
H24B | 0.7051 | 0.7367 | 0.5710 | 0.201* | |
H24C | 0.6751 | 0.6354 | 0.5957 | 0.201* | |
C25 | 0.9196 (10) | 0.6272 (3) | 0.5512 (4) | 0.112 (4)* | |
H25 | 1.0379 | 0.6526 | 0.5697 | 0.134* | |
C27 | 1.1376 (10) | 0.4682 (4) | 0.5621 (5) | 0.118 (4)* | |
H27 | 1.2556 | 0.5074 | 0.5716 | 0.141* | |
C28 | 1.1594 (12) | 0.3641 (4) | 0.5611 (6) | 0.142 (5)* | |
H28 | 1.2911 | 0.3342 | 0.5701 | 0.171* | |
C29 | 0.9903 (14) | 0.3062 (3) | 0.5470 (6) | 0.135 (5)* | |
H29 | 1.0062 | 0.2365 | 0.5463 | 0.162* | |
C30 | 0.7956 (13) | 0.3497 (3) | 0.5339 (6) | 0.124 (4)* | |
H30 | 0.6788 | 0.3095 | 0.5244 | 0.148* | |
C31 | 0.7722 (9) | 0.4540 (4) | 0.5348 (5) | 0.101 (4)* | |
H31 | 0.6401 | 0.4833 | 0.5256 | 0.121* | |
O1 | −0.087 (3) | 0.2362 (14) | 0.3636 (11) | 0.145 (13) | 0.666 (4) |
C7 | 0.088 (3) | 0.2759 (13) | 0.3534 (7) | 0.084 (8) | 0.666 (4) |
C8 | 0.2072 (13) | 0.3479 (6) | 0.3813 (5) | 0.070 (6) | 0.666 (4) |
C9 | 0.0998 (11) | 0.3821 (6) | 0.4150 (5) | 0.088 (6) | 0.666 (4) |
H9 | −0.0397 | 0.3562 | 0.4217 | 0.106* | 0.666 (4) |
C10 | 0.1935 (14) | 0.4560 (6) | 0.4402 (4) | 0.085 (6) | 0.666 (4) |
H10 | 0.1196 | 0.4776 | 0.4642 | 0.102* | 0.666 (4) |
C11 | 0.3973 (14) | 0.4978 (6) | 0.4294 (5) | 0.074 (6) | 0.666 (4) |
C12 | 0.5101 (11) | 0.4633 (7) | 0.3943 (5) | 0.085 (6) | 0.666 (4) |
H12 | 0.6488 | 0.4901 | 0.3875 | 0.102* | 0.666 (4) |
C13 | 0.4165 (14) | 0.3888 (7) | 0.3692 (5) | 0.090 (6) | 0.666 (4) |
H13 | 0.4890 | 0.3662 | 0.3451 | 0.107* | 0.666 (4) |
C15 | −0.0534 (16) | 0.4145 (6) | 0.2898 (8) | 0.081 (6) | 0.666 (4) |
H15 | −0.0728 | 0.4115 | 0.3203 | 0.097* | 0.666 (4) |
C16 | −0.2812 (15) | 0.4079 (8) | 0.2712 (10) | 0.075 (10) | 0.666 (4) |
H16A | −0.3682 | 0.4649 | 0.2798 | 0.112* | 0.666 (4) |
H16B | −0.2697 | 0.4069 | 0.2412 | 0.112* | 0.666 (4) |
H16C | −0.3531 | 0.3475 | 0.2807 | 0.112* | 0.666 (4) |
C17 | 0.0673 (15) | 0.5145 (7) | 0.2802 (10) | 0.085 (10) | 0.666 (4) |
H17A | 0.2132 | 0.5142 | 0.2930 | 0.128* | 0.666 (4) |
H17B | 0.0829 | 0.5223 | 0.2504 | 0.128* | 0.666 (4) |
H17C | −0.0192 | 0.5693 | 0.2913 | 0.128* | 0.666 (4) |
C21 | 0.399 (3) | 0.1088 (11) | 0.3330 (8) | 0.090 (6) | 0.666 (4) |
H21 | 0.4225 | 0.1488 | 0.3584 | 0.108* | 0.666 (4) |
C22 | 0.217 (3) | 0.0297 (11) | 0.3438 (15) | 0.134 (11) | 0.666 (4) |
H22A | 0.2727 | −0.0145 | 0.3652 | 0.200* | 0.666 (4) |
H22B | 0.0845 | 0.0632 | 0.3538 | 0.200* | 0.666 (4) |
H22C | 0.1809 | −0.0084 | 0.3192 | 0.200* | 0.666 (4) |
C23 | 0.618 (3) | 0.0535 (11) | 0.3247 (11) | 0.103 (11) | 0.666 (4) |
H23A | 0.6506 | 0.0100 | 0.3480 | 0.155* | 0.666 (4) |
H23B | 0.6038 | 0.0142 | 0.2996 | 0.155* | 0.666 (4) |
H23C | 0.7374 | 0.1012 | 0.3214 | 0.155* | 0.666 (4) |
O1D | −0.135 (6) | 0.266 (4) | 0.357 (2) | 0.16 (2)* | 0.260 (4) |
C7D | 0.108 (6) | 0.259 (2) | 0.3564 (8) | 0.070 (11)* | 0.260 (4) |
C8D | 0.2072 (13) | 0.3479 (6) | 0.3813 (5) | 0.070 (6) | 0.260 (4) |
C9D | 0.0998 (11) | 0.3821 (6) | 0.4150 (5) | 0.088 (6) | 0.260 (4) |
H9D | −0.0404 | 0.3561 | 0.4217 | 0.106* | 0.260 (4) |
C10D | 0.1935 (14) | 0.4560 (6) | 0.4402 (4) | 0.085 (6) | 0.260 (4) |
H10D | 0.1191 | 0.4773 | 0.4643 | 0.102* | 0.260 (4) |
C11D | 0.3973 (14) | 0.4978 (6) | 0.4294 (5) | 0.074 (6) | 0.260 (4) |
C12D | 0.5101 (11) | 0.4633 (7) | 0.3943 (5) | 0.085 (6) | 0.260 (4) |
H12D | 0.6494 | 0.4901 | 0.3875 | 0.102* | 0.260 (4) |
C13D | 0.4165 (14) | 0.3888 (7) | 0.3692 (5) | 0.090 (6) | 0.260 (4) |
H13D | 0.4895 | 0.3665 | 0.3451 | 0.107* | 0.260 (4) |
C15D | −0.0534 (16) | 0.4145 (6) | 0.2898 (8) | 0.081 (6) | 0.260 (4) |
H15D | −0.0728 | 0.4115 | 0.3203 | 0.097* | 0.260 (4) |
C16D | −0.2812 (15) | 0.4079 (8) | 0.2712 (10) | 0.075 (10) | 0.260 (4) |
H16D | −0.3682 | 0.4649 | 0.2798 | 0.112* | 0.260 (4) |
H16E | −0.2697 | 0.4069 | 0.2412 | 0.112* | 0.260 (4) |
H16F | −0.3531 | 0.3475 | 0.2807 | 0.112* | 0.260 (4) |
C17D | 0.0673 (15) | 0.5145 (7) | 0.2802 (10) | 0.085 (10) | 0.260 (4) |
H17D | 0.2132 | 0.5142 | 0.2930 | 0.128* | 0.260 (4) |
H17E | 0.0829 | 0.5223 | 0.2504 | 0.128* | 0.260 (4) |
H17F | −0.0192 | 0.5693 | 0.2913 | 0.128* | 0.260 (4) |
C21D | 0.391 (7) | 0.128 (3) | 0.3399 (10) | 0.085 (10)* | 0.260 (4) |
H21D | 0.5134 | 0.1691 | 0.3513 | 0.101* | 0.260 (4) |
C22D | 0.186 (7) | 0.152 (2) | 0.3672 (16) | 0.120 (14)* | 0.260 (4) |
H22D | 0.0666 | 0.1047 | 0.3618 | 0.144* | 0.260 (4) |
H22E | 0.2260 | 0.1485 | 0.3967 | 0.144* | 0.260 (4) |
C23D | 0.484 (10) | 0.026 (3) | 0.337 (3) | 0.132 (18)* | 0.260 (4) |
H23D | 0.5213 | 0.0015 | 0.3641 | 0.198* | 0.260 (4) |
H23E | 0.3753 | −0.0178 | 0.3240 | 0.198* | 0.260 (4) |
H23F | 0.6175 | 0.0271 | 0.3196 | 0.198* | 0.260 (4) |
O1P | −0.099 (15) | 0.253 (7) | 0.368 (2) | 0.15 (3)* | 0.075 (4) |
C7P | 0.037 (6) | 0.311 (3) | 0.3424 (11) | 0.080 (16)* | 0.075 (4) |
C8P | 0.165 (8) | 0.383 (2) | 0.3716 (11) | 0.060 (13)* | 0.075 (4) |
C9P | 0.047 (7) | 0.438 (6) | 0.399 (3) | 0.085 (7)* | 0.075 (4) |
H9P | −0.1074 | 0.4324 | 0.3990 | 0.102* | 0.075 (4) |
C10P | 0.153 (8) | 0.503 (6) | 0.426 (2) | 0.085 (7)* | 0.075 (4) |
H10P | 0.0693 | 0.5387 | 0.4458 | 0.102* | 0.075 (4) |
C11P | 0.382 (7) | 0.5136 (19) | 0.4248 (10) | 0.071 (13)* | 0.075 (4) |
C12P | 0.507 (7) | 0.457 (7) | 0.397 (3) | 0.085 (7)* | 0.075 (4) |
H12P | 0.6611 | 0.4634 | 0.3961 | 0.102* | 0.075 (4) |
C13P | 0.401 (9) | 0.392 (7) | 0.369 (3) | 0.085 (7)* | 0.075 (4) |
H13P | 0.4821 | 0.3550 | 0.3494 | 0.102* | 0.075 (4) |
C15P | −0.062 (7) | 0.384 (4) | 0.3053 (14) | 0.083 (13)* | 0.075 (4) |
C16P | −0.311 (7) | 0.375 (8) | 0.299 (4) | 0.08 (2)* | 0.075 (4) |
H16G | −0.3886 | 0.4164 | 0.3187 | 0.122* | 0.075 (4) |
H16H | −0.3483 | 0.3970 | 0.2708 | 0.122* | 0.075 (4) |
H16I | −0.3560 | 0.3065 | 0.3022 | 0.122* | 0.075 (4) |
C17P | 0.008 (18) | 0.494 (3) | 0.310 (4) | 0.09 (2)* | 0.075 (4) |
H17G | −0.0978 | 0.5283 | 0.3277 | 0.131* | 0.075 (4) |
H17H | 0.1547 | 0.4976 | 0.3224 | 0.131* | 0.075 (4) |
H17I | 0.0110 | 0.5255 | 0.2829 | 0.131* | 0.075 (4) |
C21P | 0.399 (3) | 0.1088 (11) | 0.3330 (8) | 0.090 (6) | 0.075 (4) |
H21P | 0.4225 | 0.1488 | 0.3584 | 0.108* | 0.075 (4) |
C22P | 0.217 (3) | 0.0297 (11) | 0.3438 (15) | 0.134 (11) | 0.075 (4) |
H22F | 0.2727 | −0.0145 | 0.3652 | 0.200* | 0.075 (4) |
H22G | 0.0845 | 0.0632 | 0.3538 | 0.200* | 0.075 (4) |
H22H | 0.1809 | −0.0084 | 0.3192 | 0.200* | 0.075 (4) |
C23P | 0.618 (3) | 0.0535 (11) | 0.3247 (11) | 0.103 (11) | 0.075 (4) |
H23G | 0.6506 | 0.0100 | 0.3480 | 0.155* | 0.075 (4) |
H23H | 0.6038 | 0.0142 | 0.2996 | 0.155* | 0.075 (4) |
H23I | 0.7374 | 0.1012 | 0.3214 | 0.155* | 0.075 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.101 (5) | 0.101 (4) | 0.05 (4) | 0.009 (4) | 0.000 (8) | −0.037 (7) |
O3 | 0.107 (5) | 0.133 (6) | 0.16 (5) | −0.029 (4) | 0.000 (9) | −0.034 (10) |
C6 | 0.081 (5) | 0.071 (4) | 0.07 (3) | −0.009 (4) | −0.012 (9) | −0.008 (7) |
C1 | 0.068 (4) | 0.073 (4) | 0.07 (3) | −0.007 (4) | −0.006 (8) | −0.009 (8) |
C2 | 0.070 (5) | 0.066 (4) | 0.07 (3) | 0.002 (3) | −0.011 (8) | −0.007 (8) |
C3 | 0.071 (4) | 0.076 (4) | 0.07 (3) | −0.007 (4) | −0.007 (8) | −0.005 (8) |
C4 | 0.073 (4) | 0.079 (5) | 0.07 (3) | 0.000 (4) | −0.012 (8) | −0.005 (8) |
C5 | 0.073 (4) | 0.072 (4) | 0.06 (3) | 0.001 (4) | −0.012 (8) | 0.002 (8) |
N1 | 0.100 (5) | 0.089 (5) | 0.05 (4) | 0.007 (4) | −0.009 (9) | −0.020 (8) |
O1 | 0.158 (11) | 0.125 (11) | 0.15 (4) | −0.078 (10) | 0.107 (17) | −0.072 (16) |
C7 | 0.078 (9) | 0.095 (10) | 0.08 (2) | −0.018 (9) | −0.002 (13) | 0.002 (14) |
C8 | 0.081 (5) | 0.073 (5) | 0.056 (18) | 0.003 (5) | 0.002 (9) | 0.011 (8) |
C9 | 0.087 (6) | 0.078 (5) | 0.100 (17) | −0.011 (5) | 0.000 (10) | −0.006 (9) |
C10 | 0.090 (6) | 0.091 (5) | 0.074 (17) | −0.003 (5) | −0.012 (9) | −0.001 (10) |
C11 | 0.079 (5) | 0.080 (5) | 0.063 (18) | 0.005 (5) | −0.009 (9) | 0.000 (8) |
C12 | 0.073 (5) | 0.104 (6) | 0.079 (17) | −0.010 (5) | 0.005 (10) | 0.005 (10) |
C13 | 0.088 (6) | 0.095 (6) | 0.086 (17) | −0.006 (5) | 0.014 (10) | −0.005 (10) |
C15 | 0.079 (5) | 0.067 (4) | 0.096 (18) | 0.001 (4) | 0.003 (9) | 0.005 (8) |
C16 | 0.068 (5) | 0.099 (6) | 0.06 (3) | −0.009 (4) | 0.007 (9) | 0.006 (11) |
C17 | 0.069 (5) | 0.083 (5) | 0.10 (3) | 0.000 (4) | 0.019 (9) | −0.021 (9) |
C21 | 0.116 (9) | 0.075 (7) | 0.077 (18) | 0.031 (7) | −0.001 (12) | −0.020 (10) |
C22 | 0.171 (14) | 0.099 (8) | 0.13 (3) | −0.014 (10) | 0.02 (2) | 0.027 (16) |
C23 | 0.101 (10) | 0.095 (7) | 0.11 (3) | 0.024 (7) | −0.047 (14) | −0.020 (14) |
C8D | 0.081 (5) | 0.073 (5) | 0.056 (18) | 0.003 (5) | 0.002 (9) | 0.011 (8) |
C9D | 0.087 (6) | 0.078 (5) | 0.100 (17) | −0.011 (5) | 0.000 (10) | −0.006 (9) |
C10D | 0.090 (6) | 0.091 (5) | 0.074 (17) | −0.003 (5) | −0.012 (9) | −0.001 (10) |
C11D | 0.079 (5) | 0.080 (5) | 0.063 (18) | 0.005 (5) | −0.009 (9) | 0.000 (8) |
C12D | 0.073 (5) | 0.104 (6) | 0.079 (17) | −0.010 (5) | 0.005 (10) | 0.005 (10) |
C13D | 0.088 (6) | 0.095 (6) | 0.086 (17) | −0.006 (5) | 0.014 (10) | −0.005 (10) |
C15D | 0.079 (5) | 0.067 (4) | 0.096 (18) | 0.001 (4) | 0.003 (9) | 0.005 (8) |
C16D | 0.068 (5) | 0.099 (6) | 0.06 (3) | −0.009 (4) | 0.007 (9) | 0.006 (11) |
C17D | 0.069 (5) | 0.083 (5) | 0.10 (3) | 0.000 (4) | 0.019 (9) | −0.021 (9) |
C21P | 0.116 (9) | 0.075 (7) | 0.077 (18) | 0.031 (7) | −0.001 (12) | −0.020 (10) |
C22P | 0.171 (14) | 0.099 (8) | 0.13 (3) | −0.014 (10) | 0.02 (2) | 0.027 (16) |
C23P | 0.101 (10) | 0.095 (7) | 0.11 (3) | 0.024 (7) | −0.047 (14) | −0.020 (14) |
O2—C14 | 1.23 (3) | C8—C13 | 1.4147 |
O3—C14 | 1.223 (16) | C9—C10 | 1.3885 |
C6—C1 | 1.4049 | C10—C11 | 1.3792 |
C6—C5 | 1.3986 | C11—C12 | 1.3841 |
C6—C21 | 1.513 (19) | C12—C13 | 1.3922 |
C6—C21D | 1.53 (2) | C15—C16 | 1.48 (2) |
C6—C21P | 1.513 (19) | C15—C17 | 1.545 (15) |
C1—C2 | 1.3943 | C21—C22 | 1.55 (2) |
C1—C7 | 1.53 (2) | C21—C23 | 1.521 (18) |
C1—C7D | 1.58 (2) | O1D—C7D | 1.45 (3) |
C1—C7P | 1.51 (2) | C7D—C8D | 1.55 (2) |
C2—C3 | 1.3923 | C7D—C22D | 1.53 (3) |
C2—C15 | 1.521 (12) | C8D—C9D | 1.3297 |
C2—C15D | 1.521 (12) | C8D—C13D | 1.4147 |
C2—C15P | 1.50 (2) | C9D—C10D | 1.3885 |
C3—C4 | 1.3661 | C10D—C11D | 1.3792 |
C4—C5 | 1.4075 | C11D—C12D | 1.3841 |
C4—C18 | 1.43 (3) | C12D—C13D | 1.3922 |
C14—C11 | 1.54 (2) | C15D—C16D | 1.48 (2) |
C14—C11D | 1.54 (2) | C15D—C17D | 1.545 (15) |
C14—C11P | 1.52 (2) | C21D—C22D | 1.54 (3) |
C18—C19 | 1.56 (2) | C21D—C23D | 1.48 (3) |
C18—C20 | 1.46 (4) | O1P—C7P | 1.39 (3) |
C26—C25 | 1.5154 | C7P—C8P | 1.54 (2) |
C26—C27 | 1.3713 | C7P—C15P | 1.65 (3) |
C26—C31 | 1.3757 | C8P—C9P | 1.3285 |
N1—C25 | 1.5058 | C8P—C13P | 1.4129 |
C24—C25 | 1.5008 | C9P—C10P | 1.3858 |
C27—C28 | 1.3925 | C10P—C11P | 1.3774 |
C28—C29 | 1.3453 | C11P—C12P | 1.3842 |
C29—C30 | 1.3623 | C12P—C13P | 1.3904 |
C30—C31 | 1.3962 | C15P—C16P | 1.51 (3) |
O1—C7 | 1.212 (17) | C15P—C17P | 1.53 (3) |
C7—C8 | 1.489 (17) | C21P—C22P | 1.55 (2) |
C8—C9 | 1.3297 | C21P—C23P | 1.521 (18) |
C1—C6—C21 | 121.5 (10) | C12—C11—C14 | 119.0 (11) |
C1—C6—C21D | 109.9 (14) | C11—C12—C13 | 120.6 |
C1—C6—C21P | 121.5 (10) | C12—C13—C8 | 118.0 |
C5—C6—C1 | 116.4 | C2—C15—C17 | 109.6 (10) |
C5—C6—C21 | 122.1 (10) | C16—C15—C2 | 113.6 (13) |
C5—C6—C21D | 133.6 (13) | C16—C15—C17 | 113.5 (14) |
C5—C6—C21P | 122.1 (10) | C6—C21—C22 | 112.1 (18) |
C6—C1—C7 | 120.3 (9) | C6—C21—C23 | 116.7 (19) |
C6—C1—C7D | 110.1 (13) | C23—C21—C22 | 108.0 (12) |
C6—C1—C7P | 145.0 (19) | O1D—C7D—C1 | 105 (3) |
C2—C1—C6 | 122.3 | O1D—C7D—C8D | 109 (3) |
C2—C1—C7 | 117.4 (9) | O1D—C7D—C22D | 111 (3) |
C2—C1—C7D | 127.5 (13) | C8D—C7D—C1 | 112.3 (17) |
C2—C1—C7P | 92.5 (19) | C22D—C7D—C1 | 99 (2) |
C1—C2—C15 | 120.3 (11) | C22D—C7D—C8D | 119 (3) |
C1—C2—C15D | 120.3 (11) | C9D—C8D—C7D | 119.7 (12) |
C1—C2—C15P | 97.0 (19) | C9D—C8D—C13D | 120.9 |
C3—C2—C1 | 118.2 | C13D—C8D—C7D | 119.4 (12) |
C3—C2—C15 | 121.5 (11) | C8D—C9D—C10D | 121.2 |
C3—C2—C15D | 121.5 (11) | C11D—C10D—C9D | 119.7 |
C3—C2—C15P | 144.1 (18) | C10D—C11D—C14 | 121.3 (10) |
C4—C3—C2 | 122.6 | C10D—C11D—C12D | 119.7 |
C3—C4—C5 | 117.7 | C12D—C11D—C14 | 119.0 (11) |
C3—C4—C18 | 127.7 (10) | C11D—C12D—C13D | 120.6 |
C5—C4—C18 | 114.4 (10) | C12D—C13D—C8D | 118.0 |
C6—C5—C4 | 122.8 | C2—C15D—C17D | 109.6 (10) |
O2—C14—C11 | 117.9 (10) | C16D—C15D—C2 | 113.6 (13) |
O2—C14—C11D | 117.9 (10) | C16D—C15D—C17D | 113.5 (14) |
O2—C14—C11P | 117 (2) | C6—C21D—C22D | 100 (3) |
O3—C14—O2 | 123.9 (16) | C23D—C21D—C6 | 118 (4) |
O3—C14—C11 | 118.1 (19) | C23D—C21D—C22D | 122 (4) |
O3—C14—C11D | 118.1 (19) | C7D—C22D—C21D | 108 (3) |
O3—C14—C11P | 118 (2) | C1—C7P—C8P | 115 (2) |
C4—C18—C19 | 115 (2) | C1—C7P—C15P | 86.7 (19) |
C4—C18—C20 | 111.1 (17) | O1P—C7P—C1 | 120 (4) |
C20—C18—C19 | 109 (2) | O1P—C7P—C8P | 106 (3) |
C27—C26—C25 | 120.6 | O1P—C7P—C15P | 123 (4) |
C27—C26—C31 | 117.8 | C8P—C7P—C15P | 103.8 (18) |
C31—C26—C25 | 121.6 | C9P—C8P—C7P | 118 (3) |
N1—C25—C26 | 109.8 | C9P—C8P—C13P | 121.0 |
C24—C25—C26 | 115.4 | C13P—C8P—C7P | 121 (3) |
C24—C25—N1 | 109.2 | C8P—C9P—C10P | 121.16 (8) |
C26—C27—C28 | 121.0 | C11P—C10P—C9P | 119.7 |
C29—C28—C27 | 120.6 | C10P—C11P—C14 | 120 (3) |
C28—C29—C30 | 119.7 | C10P—C11P—C12P | 119.7 |
C29—C30—C31 | 120.1 | C12P—C11P—C14 | 121 (3) |
C26—C31—C30 | 120.8 | C11P—C12P—C13P | 120.60 (9) |
O1—C7—C1 | 119.3 (18) | C12P—C13P—C8P | 117.9 |
O1—C7—C8 | 122.0 (19) | C2—C15P—C7P | 83.6 (18) |
C8—C7—C1 | 118.3 (11) | C2—C15P—C16P | 120 (4) |
C9—C8—C7 | 118.3 (9) | C2—C15P—C17P | 112 (4) |
C9—C8—C13 | 120.9 | C16P—C15P—C7P | 114 (4) |
C13—C8—C7 | 120.3 (9) | C16P—C15P—C17P | 111 (3) |
C8—C9—C10 | 121.2 | C17P—C15P—C7P | 114 (4) |
C11—C10—C9 | 119.7 | C6—C21P—C22P | 112.1 (18) |
C10—C11—C14 | 121.3 (10) | C6—C21P—C23P | 116.7 (19) |
C10—C11—C12 | 119.7 | C23P—C21P—C22P | 108.0 (12) |
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