Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700428X/bt2256sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680700428X/bt2256Isup2.hkl |
CCDC reference: 618046
Data collection: RAPID-AUTO (Rigaku, 2000); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.
C21H27NO | F(000) = 672 |
Mr = 309.44 | Dx = 1.114 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2697 (13) Å | Cell parameters from 10713 reflections |
b = 16.168 (3) Å | θ = 2.6–25.0° |
c = 18.260 (4) Å | µ = 0.07 mm−1 |
β = 94.60 (3)° | T = 293 K |
V = 1845.0 (6) Å3 | Block, colourless |
Z = 4 | 0.50 × 0.45 × 0.12 mm |
Rigaku R-AXIS RAPID image-plate diffractometer | 3389 independent reflections |
Radiation source: fine-focus sealed tube | 2089 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 10.00 pixels mm-1 | θmax = 25.0°, θmin = 2.6° |
Ω scans | h = −7→7 |
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995) | k = −19→19 |
Tmin = 0.967, Tmax = 0.992 | l = −21→21 |
10713 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: geom or difmap |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.027P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.001 |
3389 reflections | Δρmax = 0.16 e Å−3 |
424 parameters | Δρmin = −0.13 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.074 (2) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4567 (3) | 0.9951 (2) | 0.90945 (11) | 0.0538 (6) | |
HO1 | 0.481 (6) | 1.055 (3) | 0.9099 (19) | 0.097 (14)* | |
O2 | 0.5526 (3) | 0.4558 (2) | 0.55357 (13) | 0.0549 (6) | |
HO2 | 0.559 (6) | 0.421 (2) | 0.515 (2) | 0.098 (16)* | |
N1 | 0.6059 (5) | 1.15110 (18) | 0.87459 (14) | 0.0621 (8) | |
N2 | 0.6158 (4) | 0.32346 (18) | 0.46635 (13) | 0.0563 (7) | |
C1 | 0.6550 (6) | 1.1077 (2) | 0.80766 (17) | 0.0635 (10) | |
H1A | 0.7009 | 1.1481 | 0.7729 | 0.076* | |
H1B | 0.5249 | 1.0823 | 0.7859 | 0.076* | |
C2 | 0.8257 (5) | 1.0418 (2) | 0.81882 (14) | 0.0552 (9) | |
H2 | 0.9710 | 1.0623 | 0.8140 | 0.066* | |
C3 | 0.8165 (5) | 0.96729 (19) | 0.87137 (14) | 0.0496 (8) | |
H3 | 0.9603 | 0.9509 | 0.8911 | 0.060* | |
C4 | 0.6514 (5) | 0.9497 (2) | 0.92625 (15) | 0.0454 (8) | |
C5 | 0.7349 (5) | 0.97082 (18) | 1.00602 (15) | 0.0484 (8) | |
C6 | 0.9350 (6) | 1.0016 (2) | 1.02677 (18) | 0.0659 (10) | |
H6 | 1.0308 | 1.0114 | 0.9914 | 0.079* | |
C7 | 0.9949 (7) | 1.0183 (2) | 1.0998 (2) | 0.0812 (13) | |
H7 | 1.1294 | 1.0405 | 1.1129 | 0.097* | |
C8 | 0.8591 (8) | 1.0026 (2) | 1.1529 (2) | 0.0803 (12) | |
H8 | 0.9018 | 1.0132 | 1.2020 | 0.096* | |
C9 | 0.6600 (8) | 0.9712 (2) | 1.13356 (18) | 0.0746 (11) | |
H9 | 0.5664 | 0.9607 | 1.1694 | 0.089* | |
C10 | 0.5980 (6) | 0.9551 (2) | 1.06044 (17) | 0.0608 (9) | |
H10 | 0.4627 | 0.9336 | 1.0476 | 0.073* | |
C11 | 0.5993 (5) | 0.85797 (19) | 0.92379 (15) | 0.0446 (8) | |
C12 | 0.3978 (6) | 0.8279 (2) | 0.90163 (17) | 0.0621 (9) | |
H12 | 0.2883 | 0.8648 | 0.8876 | 0.075* | |
C13 | 0.3566 (7) | 0.7438 (3) | 0.9000 (2) | 0.0742 (11) | |
H13 | 0.2198 | 0.7248 | 0.8852 | 0.089* | |
C14 | 0.5159 (8) | 0.6884 (2) | 0.9198 (2) | 0.0783 (13) | |
H14 | 0.4877 | 0.6319 | 0.9185 | 0.094* | |
C15 | 0.7172 (8) | 0.7166 (2) | 0.94171 (19) | 0.0735 (12) | |
H15 | 0.8257 | 0.6792 | 0.9557 | 0.088* | |
C16 | 0.7587 (6) | 0.8005 (2) | 0.94301 (16) | 0.0576 (9) | |
H16 | 0.8964 | 0.8189 | 0.9571 | 0.069* | |
C17 | 0.7876 (5) | 0.9540 (2) | 0.78896 (15) | 0.0509 (8) | |
C18 | 0.5734 (5) | 0.9311 (2) | 0.75188 (16) | 0.0690 (11) | |
H18A | 0.4626 | 0.9586 | 0.7758 | 0.103* | |
H18B | 0.5538 | 0.8723 | 0.7548 | 0.103* | |
H18C | 0.5669 | 0.9476 | 0.7012 | 0.103* | |
C19 | 0.9706 (6) | 0.9121 (2) | 0.75433 (17) | 0.0736 (11) | |
H19A | 1.1037 | 0.9279 | 0.7802 | 0.110* | |
H19B | 0.9702 | 0.9285 | 0.7038 | 0.110* | |
H19C | 0.9538 | 0.8531 | 0.7571 | 0.110* | |
C20 | 0.7942 (7) | 1.1954 (3) | 0.9070 (2) | 0.0894 (13) | |
H20A | 0.7590 | 1.2230 | 0.9510 | 0.134* | |
H20B | 0.8389 | 1.2355 | 0.8726 | 0.134* | |
H20C | 0.9082 | 1.1568 | 0.9187 | 0.134* | |
C21 | 0.4286 (7) | 1.2093 (2) | 0.8572 (2) | 0.0914 (13) | |
H21A | 0.3066 | 1.1797 | 0.8356 | 0.137* | |
H21B | 0.4717 | 1.2502 | 0.8233 | 0.137* | |
H21C | 0.3919 | 1.2359 | 0.9015 | 0.137* | |
C22 | 0.6997 (6) | 0.2854 (2) | 0.53611 (17) | 0.0652 (10) | |
H22A | 0.7317 | 0.2278 | 0.5271 | 0.078* | |
H22B | 0.5885 | 0.2869 | 0.5701 | 0.078* | |
C23 | 0.8972 (5) | 0.32602 (19) | 0.57201 (15) | 0.0517 (8) | |
H23 | 1.0298 | 0.2993 | 0.5595 | 0.062* | |
C24 | 0.9255 (5) | 0.41844 (18) | 0.58918 (15) | 0.0478 (8) | |
H24 | 1.0736 | 0.4364 | 0.5857 | 0.057* | |
C25 | 0.7665 (5) | 0.48670 (18) | 0.56599 (15) | 0.0445 (8) | |
C26 | 0.7655 (5) | 0.55076 (19) | 0.62732 (15) | 0.0473 (8) | |
C27 | 0.9439 (6) | 0.5995 (2) | 0.64531 (17) | 0.0579 (9) | |
H27 | 1.0637 | 0.5941 | 0.6187 | 0.070* | |
C28 | 0.9467 (7) | 0.6563 (2) | 0.70243 (19) | 0.0689 (11) | |
H28 | 1.0685 | 0.6880 | 0.7141 | 0.083* | |
C29 | 0.7714 (8) | 0.6661 (2) | 0.74170 (19) | 0.0735 (11) | |
H29 | 0.7737 | 0.7040 | 0.7801 | 0.088* | |
C30 | 0.5910 (7) | 0.6190 (3) | 0.7237 (2) | 0.0769 (11) | |
H30 | 0.4705 | 0.6258 | 0.7497 | 0.092* | |
C31 | 0.5882 (6) | 0.5619 (2) | 0.66747 (18) | 0.0639 (10) | |
H31 | 0.4659 | 0.5305 | 0.6562 | 0.077* | |
C32 | 0.8254 (5) | 0.52993 (18) | 0.49466 (16) | 0.0463 (8) | |
C33 | 1.0225 (6) | 0.5258 (2) | 0.46656 (18) | 0.0657 (10) | |
H33 | 1.1318 | 0.4952 | 0.4911 | 0.079* | |
C34 | 1.0599 (7) | 0.5669 (2) | 0.4016 (2) | 0.0775 (11) | |
H34 | 1.1945 | 0.5640 | 0.3837 | 0.093* | |
C35 | 0.9025 (9) | 0.6109 (2) | 0.3643 (2) | 0.0819 (12) | |
H35 | 0.9271 | 0.6365 | 0.3201 | 0.098* | |
C36 | 0.7087 (8) | 0.6173 (3) | 0.3919 (2) | 0.0832 (12) | |
H36 | 0.6015 | 0.6490 | 0.3675 | 0.100* | |
C37 | 0.6699 (6) | 0.5769 (2) | 0.45641 (19) | 0.0672 (10) | |
H37 | 0.5357 | 0.5815 | 0.4744 | 0.081* | |
C38 | 0.9078 (5) | 0.35643 (19) | 0.65091 (17) | 0.0507 (8) | |
C39 | 1.1132 (6) | 0.3378 (2) | 0.69741 (19) | 0.0777 (11) | |
H39A | 1.2316 | 0.3399 | 0.6672 | 0.116* | |
H39B | 1.1045 | 0.2836 | 0.7185 | 0.116* | |
H39C | 1.1336 | 0.3781 | 0.7360 | 0.116* | |
C40 | 0.7142 (6) | 0.3532 (2) | 0.69333 (18) | 0.0746 (11) | |
H40A | 0.7318 | 0.3105 | 0.7299 | 0.112* | |
H40B | 0.5905 | 0.3414 | 0.6606 | 0.112* | |
H40C | 0.6958 | 0.4055 | 0.7169 | 0.112* | |
C41 | 0.4150 (6) | 0.2827 (3) | 0.43890 (19) | 0.0861 (13) | |
H41A | 0.3139 | 0.2858 | 0.4756 | 0.129* | |
H41B | 0.4429 | 0.2258 | 0.4282 | 0.129* | |
H41C | 0.3573 | 0.3100 | 0.3950 | 0.129* | |
C42 | 0.7733 (6) | 0.3204 (3) | 0.41183 (18) | 0.0894 (13) | |
H42A | 0.7149 | 0.3459 | 0.3671 | 0.134* | |
H42B | 0.8086 | 0.2639 | 0.4024 | 0.134* | |
H42C | 0.9000 | 0.3496 | 0.4301 | 0.134* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0441 (15) | 0.0572 (16) | 0.0609 (14) | 0.0073 (12) | 0.0087 (11) | 0.0137 (12) |
O2 | 0.0414 (15) | 0.0559 (14) | 0.0673 (15) | −0.0030 (12) | 0.0043 (11) | −0.0010 (13) |
N1 | 0.074 (2) | 0.0601 (18) | 0.0533 (17) | 0.0034 (17) | 0.0127 (16) | 0.0062 (15) |
N2 | 0.0567 (19) | 0.0626 (18) | 0.0491 (15) | −0.0036 (16) | 0.0016 (14) | 0.0005 (15) |
C1 | 0.080 (3) | 0.056 (2) | 0.055 (2) | 0.010 (2) | 0.0128 (19) | 0.0132 (18) |
C2 | 0.052 (2) | 0.067 (2) | 0.0475 (18) | −0.0064 (19) | 0.0055 (16) | 0.0105 (18) |
C3 | 0.0388 (19) | 0.062 (2) | 0.0487 (17) | 0.0012 (17) | 0.0071 (14) | 0.0104 (17) |
C4 | 0.038 (2) | 0.0494 (18) | 0.0488 (18) | 0.0008 (17) | 0.0044 (15) | 0.0077 (16) |
C5 | 0.060 (2) | 0.0406 (18) | 0.0450 (17) | −0.0001 (17) | 0.0051 (16) | 0.0051 (16) |
C6 | 0.073 (3) | 0.070 (2) | 0.054 (2) | −0.015 (2) | −0.0005 (18) | 0.0041 (18) |
C7 | 0.103 (3) | 0.074 (3) | 0.063 (2) | −0.030 (3) | −0.013 (2) | 0.004 (2) |
C8 | 0.123 (4) | 0.063 (2) | 0.052 (2) | −0.010 (3) | −0.007 (3) | −0.0036 (19) |
C9 | 0.112 (4) | 0.064 (2) | 0.050 (2) | −0.001 (3) | 0.015 (2) | 0.001 (2) |
C10 | 0.071 (3) | 0.062 (2) | 0.0504 (19) | 0.002 (2) | 0.0104 (18) | −0.0005 (18) |
C11 | 0.045 (2) | 0.050 (2) | 0.0389 (16) | 0.0017 (18) | 0.0066 (15) | 0.0007 (16) |
C12 | 0.056 (3) | 0.068 (3) | 0.062 (2) | −0.007 (2) | 0.0055 (19) | 0.006 (2) |
C13 | 0.073 (3) | 0.075 (3) | 0.077 (3) | −0.021 (3) | 0.015 (2) | −0.006 (2) |
C14 | 0.116 (4) | 0.054 (2) | 0.068 (3) | −0.014 (3) | 0.028 (3) | −0.012 (2) |
C15 | 0.101 (4) | 0.049 (2) | 0.071 (3) | 0.010 (3) | 0.010 (2) | −0.006 (2) |
C16 | 0.063 (3) | 0.053 (2) | 0.057 (2) | 0.006 (2) | 0.0021 (18) | −0.0016 (17) |
C17 | 0.046 (2) | 0.064 (2) | 0.0439 (17) | −0.0024 (19) | 0.0092 (15) | 0.0009 (17) |
C18 | 0.065 (3) | 0.092 (3) | 0.0494 (18) | −0.008 (2) | 0.0006 (17) | −0.0035 (19) |
C19 | 0.069 (3) | 0.090 (3) | 0.065 (2) | 0.013 (2) | 0.023 (2) | 0.004 (2) |
C20 | 0.111 (4) | 0.078 (3) | 0.080 (3) | −0.014 (3) | 0.015 (3) | −0.014 (2) |
C21 | 0.119 (4) | 0.075 (3) | 0.083 (3) | 0.036 (3) | 0.030 (2) | 0.018 (2) |
C22 | 0.087 (3) | 0.049 (2) | 0.057 (2) | −0.009 (2) | −0.0048 (19) | −0.0002 (18) |
C23 | 0.053 (2) | 0.048 (2) | 0.0535 (19) | 0.0044 (18) | 0.0021 (16) | −0.0003 (16) |
C24 | 0.036 (2) | 0.052 (2) | 0.0557 (19) | 0.0012 (17) | 0.0053 (16) | 0.0060 (17) |
C25 | 0.035 (2) | 0.0447 (18) | 0.0537 (19) | 0.0005 (16) | 0.0030 (15) | −0.0008 (16) |
C26 | 0.050 (2) | 0.0462 (19) | 0.0465 (17) | 0.0053 (18) | 0.0081 (16) | 0.0062 (15) |
C27 | 0.060 (2) | 0.062 (2) | 0.052 (2) | −0.006 (2) | 0.0089 (18) | 0.0011 (18) |
C28 | 0.084 (3) | 0.066 (2) | 0.056 (2) | −0.009 (2) | 0.000 (2) | 0.000 (2) |
C29 | 0.116 (4) | 0.055 (2) | 0.052 (2) | 0.007 (3) | 0.018 (2) | −0.0008 (18) |
C30 | 0.088 (3) | 0.074 (3) | 0.072 (3) | 0.015 (3) | 0.030 (2) | −0.003 (2) |
C31 | 0.060 (3) | 0.061 (2) | 0.072 (2) | 0.003 (2) | 0.015 (2) | −0.005 (2) |
C32 | 0.048 (2) | 0.0415 (18) | 0.0499 (18) | 0.0016 (17) | 0.0042 (17) | −0.0002 (16) |
C33 | 0.062 (3) | 0.070 (3) | 0.067 (2) | 0.002 (2) | 0.013 (2) | 0.011 (2) |
C34 | 0.087 (3) | 0.077 (3) | 0.073 (2) | −0.012 (3) | 0.032 (2) | 0.007 (2) |
C35 | 0.129 (4) | 0.062 (2) | 0.057 (2) | 0.003 (3) | 0.019 (3) | 0.008 (2) |
C36 | 0.110 (4) | 0.084 (3) | 0.056 (2) | 0.024 (3) | 0.008 (2) | 0.010 (2) |
C37 | 0.074 (3) | 0.070 (2) | 0.058 (2) | 0.012 (2) | 0.010 (2) | 0.001 (2) |
C38 | 0.048 (2) | 0.053 (2) | 0.0508 (18) | 0.0012 (18) | 0.0020 (17) | 0.0034 (17) |
C39 | 0.076 (3) | 0.069 (2) | 0.082 (2) | 0.012 (2) | −0.025 (2) | −0.002 (2) |
C40 | 0.080 (3) | 0.083 (3) | 0.062 (2) | −0.008 (2) | 0.009 (2) | 0.014 (2) |
C41 | 0.088 (3) | 0.101 (3) | 0.067 (2) | −0.023 (3) | −0.007 (2) | −0.006 (2) |
C42 | 0.086 (3) | 0.126 (4) | 0.058 (2) | 0.016 (3) | 0.018 (2) | −0.002 (2) |
O1—C4 | 1.436 (4) | C20—H20B | 0.9600 |
O1—HO1 | 0.98 (4) | C20—H20C | 0.9600 |
O2—C25 | 1.432 (4) | C21—H21A | 0.9600 |
O2—HO2 | 0.90 (4) | C21—H21B | 0.9600 |
N1—C1 | 1.463 (4) | C21—H21C | 0.9600 |
N1—C20 | 1.466 (4) | C22—C23 | 1.505 (4) |
N1—C21 | 1.471 (4) | C22—H22A | 0.9700 |
N2—C42 | 1.458 (4) | C22—H22B | 0.9700 |
N2—C41 | 1.473 (4) | C23—C38 | 1.519 (4) |
N2—C22 | 1.473 (4) | C23—C24 | 1.534 (4) |
C1—C2 | 1.513 (4) | C23—H23 | 0.9800 |
C1—H1A | 0.9700 | C24—C38 | 1.519 (4) |
C1—H1B | 0.9700 | C24—C25 | 1.524 (4) |
C2—C17 | 1.532 (4) | C24—H24 | 0.9800 |
C2—C3 | 1.544 (4) | C25—C26 | 1.526 (4) |
C2—H2 | 0.9800 | C25—C32 | 1.549 (4) |
C3—C17 | 1.516 (4) | C26—C27 | 1.386 (4) |
C3—C4 | 1.524 (4) | C26—C31 | 1.392 (4) |
C3—H3 | 0.9800 | C27—C28 | 1.389 (5) |
C4—C11 | 1.518 (4) | C27—H27 | 0.9300 |
C4—C5 | 1.546 (4) | C28—C29 | 1.368 (5) |
C5—C6 | 1.374 (4) | C28—H28 | 0.9300 |
C5—C10 | 1.388 (4) | C29—C30 | 1.382 (5) |
C6—C7 | 1.383 (4) | C29—H29 | 0.9300 |
C6—H6 | 0.9300 | C30—C31 | 1.379 (5) |
C7—C8 | 1.365 (5) | C30—H30 | 0.9300 |
C7—H7 | 0.9300 | C31—H31 | 0.9300 |
C8—C9 | 1.368 (5) | C32—C33 | 1.377 (4) |
C8—H8 | 0.9300 | C32—C37 | 1.380 (4) |
C9—C10 | 1.385 (4) | C33—C34 | 1.397 (5) |
C9—H9 | 0.9300 | C33—H33 | 0.9300 |
C10—H10 | 0.9300 | C34—C35 | 1.355 (5) |
C11—C12 | 1.383 (4) | C34—H34 | 0.9300 |
C11—C16 | 1.389 (4) | C35—C36 | 1.357 (5) |
C12—C13 | 1.384 (5) | C35—H35 | 0.9300 |
C12—H12 | 0.9300 | C36—C37 | 1.385 (5) |
C13—C14 | 1.368 (5) | C36—H36 | 0.9300 |
C13—H13 | 0.9300 | C37—H37 | 0.9300 |
C14—C15 | 1.371 (5) | C38—C40 | 1.492 (4) |
C14—H14 | 0.9300 | C38—C39 | 1.515 (4) |
C15—C16 | 1.382 (5) | C39—H39A | 0.9600 |
C15—H15 | 0.9300 | C39—H39B | 0.9600 |
C16—H16 | 0.9300 | C39—H39C | 0.9600 |
C17—C18 | 1.501 (4) | C40—H40A | 0.9600 |
C17—C19 | 1.514 (4) | C40—H40B | 0.9600 |
C18—H18A | 0.9600 | C40—H40C | 0.9600 |
C18—H18B | 0.9600 | C41—H41A | 0.9600 |
C18—H18C | 0.9600 | C41—H41B | 0.9600 |
C19—H19A | 0.9600 | C41—H41C | 0.9600 |
C19—H19B | 0.9600 | C42—H42A | 0.9600 |
C19—H19C | 0.9600 | C42—H42B | 0.9600 |
C20—H20A | 0.9600 | C42—H42C | 0.9600 |
C4—O1—HO1 | 112 (2) | H21A—C21—H21B | 109.5 |
C25—O2—HO2 | 104 (3) | N1—C21—H21C | 109.5 |
C1—N1—C20 | 110.8 (3) | H21A—C21—H21C | 109.5 |
C1—N1—C21 | 109.4 (3) | H21B—C21—H21C | 109.5 |
C20—N1—C21 | 110.2 (3) | N2—C22—C23 | 114.8 (3) |
C42—N2—C41 | 111.1 (3) | N2—C22—H22A | 108.6 |
C42—N2—C22 | 111.3 (3) | C23—C22—H22A | 108.6 |
C41—N2—C22 | 110.1 (3) | N2—C22—H22B | 108.6 |
N1—C1—C2 | 114.8 (3) | C23—C22—H22B | 108.6 |
N1—C1—H1A | 108.6 | H22A—C22—H22B | 107.6 |
C2—C1—H1A | 108.6 | C22—C23—C38 | 121.8 (3) |
N1—C1—H1B | 108.6 | C22—C23—C24 | 126.2 (3) |
C2—C1—H1B | 108.6 | C38—C23—C24 | 59.69 (19) |
H1A—C1—H1B | 107.5 | C22—C23—H23 | 113.0 |
C1—C2—C17 | 121.1 (3) | C38—C23—H23 | 113.0 |
C1—C2—C3 | 124.9 (3) | C24—C23—H23 | 113.0 |
C17—C2—C3 | 59.09 (19) | C38—C24—C25 | 126.8 (3) |
C1—C2—H2 | 113.7 | C38—C24—C23 | 59.65 (19) |
C17—C2—H2 | 113.7 | C25—C24—C23 | 125.9 (3) |
C3—C2—H2 | 113.7 | C38—C24—H24 | 111.7 |
C17—C3—C4 | 126.3 (3) | C25—C24—H24 | 111.7 |
C17—C3—C2 | 60.05 (19) | C23—C24—H24 | 111.7 |
C4—C3—C2 | 128.0 (3) | O2—C25—C24 | 112.0 (3) |
C17—C3—H3 | 111.1 | O2—C25—C26 | 107.1 (3) |
C4—C3—H3 | 111.1 | C24—C25—C26 | 109.2 (2) |
C2—C3—H3 | 111.1 | O2—C25—C32 | 107.9 (2) |
O1—C4—C11 | 108.4 (3) | C24—C25—C32 | 111.5 (2) |
O1—C4—C3 | 112.0 (2) | C26—C25—C32 | 109.0 (2) |
C11—C4—C3 | 108.6 (3) | C27—C26—C31 | 117.7 (3) |
O1—C4—C5 | 107.8 (2) | C27—C26—C25 | 120.6 (3) |
C11—C4—C5 | 107.4 (2) | C31—C26—C25 | 121.7 (3) |
C3—C4—C5 | 112.4 (3) | C26—C27—C28 | 121.0 (3) |
C6—C5—C10 | 118.2 (3) | C26—C27—H27 | 119.5 |
C6—C5—C4 | 124.9 (3) | C28—C27—H27 | 119.5 |
C10—C5—C4 | 116.9 (3) | C29—C28—C27 | 120.5 (4) |
C5—C6—C7 | 120.5 (3) | C29—C28—H28 | 119.7 |
C5—C6—H6 | 119.7 | C27—C28—H28 | 119.7 |
C7—C6—H6 | 119.7 | C28—C29—C30 | 119.2 (3) |
C8—C7—C6 | 120.9 (4) | C28—C29—H29 | 120.4 |
C8—C7—H7 | 119.6 | C30—C29—H29 | 120.4 |
C6—C7—H7 | 119.6 | C31—C30—C29 | 120.5 (4) |
C7—C8—C9 | 119.6 (3) | C31—C30—H30 | 119.8 |
C7—C8—H8 | 120.2 | C29—C30—H30 | 119.8 |
C9—C8—H8 | 120.2 | C30—C31—C26 | 121.1 (4) |
C8—C9—C10 | 119.9 (4) | C30—C31—H31 | 119.5 |
C8—C9—H9 | 120.0 | C26—C31—H31 | 119.5 |
C10—C9—H9 | 120.0 | C33—C32—C37 | 117.2 (3) |
C9—C10—C5 | 120.9 (4) | C33—C32—C25 | 124.9 (3) |
C9—C10—H10 | 119.5 | C37—C32—C25 | 117.9 (3) |
C5—C10—H10 | 119.5 | C32—C33—C34 | 120.7 (4) |
C12—C11—C16 | 117.4 (3) | C32—C33—H33 | 119.7 |
C12—C11—C4 | 122.7 (3) | C34—C33—H33 | 119.7 |
C16—C11—C4 | 119.8 (3) | C35—C34—C33 | 120.8 (4) |
C11—C12—C13 | 121.1 (4) | C35—C34—H34 | 119.6 |
C11—C12—H12 | 119.5 | C33—C34—H34 | 119.6 |
C13—C12—H12 | 119.5 | C34—C35—C36 | 119.4 (4) |
C14—C13—C12 | 120.4 (4) | C34—C35—H35 | 120.3 |
C14—C13—H13 | 119.8 | C36—C35—H35 | 120.3 |
C12—C13—H13 | 119.8 | C35—C36—C37 | 120.3 (4) |
C13—C14—C15 | 119.7 (4) | C35—C36—H36 | 119.9 |
C13—C14—H14 | 120.2 | C37—C36—H36 | 119.9 |
C15—C14—H14 | 120.2 | C32—C37—C36 | 121.6 (4) |
C14—C15—C16 | 120.0 (4) | C32—C37—H37 | 119.2 |
C14—C15—H15 | 120.0 | C36—C37—H37 | 119.2 |
C16—C15—H15 | 120.0 | C40—C38—C39 | 113.1 (3) |
C15—C16—C11 | 121.5 (4) | C40—C38—C23 | 120.4 (3) |
C15—C16—H16 | 119.3 | C39—C38—C23 | 116.0 (3) |
C11—C16—H16 | 119.3 | C40—C38—C24 | 121.3 (3) |
C18—C17—C19 | 112.4 (3) | C39—C38—C24 | 116.0 (3) |
C18—C17—C3 | 120.9 (3) | C23—C38—C24 | 60.66 (19) |
C19—C17—C3 | 116.3 (3) | C38—C39—H39A | 109.5 |
C18—C17—C2 | 119.9 (3) | C38—C39—H39B | 109.5 |
C19—C17—C2 | 117.5 (3) | H39A—C39—H39B | 109.5 |
C3—C17—C2 | 60.86 (19) | C38—C39—H39C | 109.5 |
C17—C18—H18A | 109.5 | H39A—C39—H39C | 109.5 |
C17—C18—H18B | 109.5 | H39B—C39—H39C | 109.5 |
H18A—C18—H18B | 109.5 | C38—C40—H40A | 109.5 |
C17—C18—H18C | 109.5 | C38—C40—H40B | 109.5 |
H18A—C18—H18C | 109.5 | H40A—C40—H40B | 109.5 |
H18B—C18—H18C | 109.5 | C38—C40—H40C | 109.5 |
C17—C19—H19A | 109.5 | H40A—C40—H40C | 109.5 |
C17—C19—H19B | 109.5 | H40B—C40—H40C | 109.5 |
H19A—C19—H19B | 109.5 | N2—C41—H41A | 109.5 |
C17—C19—H19C | 109.5 | N2—C41—H41B | 109.5 |
H19A—C19—H19C | 109.5 | H41A—C41—H41B | 109.5 |
H19B—C19—H19C | 109.5 | N2—C41—H41C | 109.5 |
N1—C20—H20A | 109.5 | H41A—C41—H41C | 109.5 |
N1—C20—H20B | 109.5 | H41B—C41—H41C | 109.5 |
H20A—C20—H20B | 109.5 | N2—C42—H42A | 109.5 |
N1—C20—H20C | 109.5 | N2—C42—H42B | 109.5 |
H20A—C20—H20C | 109.5 | H42A—C42—H42B | 109.5 |
H20B—C20—H20C | 109.5 | N2—C42—H42C | 109.5 |
N1—C21—H21A | 109.5 | H42A—C42—H42C | 109.5 |
N1—C21—H21B | 109.5 | H42B—C42—H42C | 109.5 |
C20—N1—C1—C2 | 62.1 (4) | C42—N2—C22—C23 | 60.4 (4) |
C21—N1—C1—C2 | −176.2 (3) | C41—N2—C22—C23 | −176.0 (3) |
N1—C1—C2—C17 | 128.8 (3) | N2—C22—C23—C38 | 125.7 (3) |
N1—C1—C2—C3 | 56.9 (4) | N2—C22—C23—C24 | 52.1 (4) |
C1—C2—C3—C17 | 108.4 (3) | C22—C23—C24—C38 | 109.1 (3) |
C1—C2—C3—C4 | −6.3 (5) | C22—C23—C24—C25 | −6.6 (5) |
C17—C2—C3—C4 | −114.7 (3) | C38—C23—C24—C25 | −115.7 (3) |
C17—C3—C4—O1 | −58.2 (4) | C38—C24—C25—O2 | −51.7 (4) |
C2—C3—C4—O1 | 19.6 (4) | C23—C24—C25—O2 | 24.6 (4) |
C17—C3—C4—C11 | 61.5 (4) | C38—C24—C25—C26 | 66.8 (4) |
C2—C3—C4—C11 | 139.3 (3) | C23—C24—C25—C26 | 143.0 (3) |
C17—C3—C4—C5 | −179.8 (3) | C38—C24—C25—C32 | −172.7 (3) |
C2—C3—C4—C5 | −102.0 (3) | C23—C24—C25—C32 | −96.4 (3) |
O1—C4—C5—C6 | −124.3 (3) | O2—C25—C26—C27 | −171.6 (3) |
C11—C4—C5—C6 | 119.1 (3) | C24—C25—C26—C27 | 66.9 (3) |
C3—C4—C5—C6 | −0.3 (4) | C32—C25—C26—C27 | −55.1 (4) |
O1—C4—C5—C10 | 57.5 (4) | O2—C25—C26—C31 | 9.0 (4) |
C11—C4—C5—C10 | −59.2 (4) | C24—C25—C26—C31 | −112.5 (3) |
C3—C4—C5—C10 | −178.5 (3) | C32—C25—C26—C31 | 125.5 (3) |
C10—C5—C6—C7 | −1.6 (5) | C31—C26—C27—C28 | 1.2 (5) |
C4—C5—C6—C7 | −179.8 (3) | C25—C26—C27—C28 | −178.2 (3) |
C5—C6—C7—C8 | 1.7 (5) | C26—C27—C28—C29 | −0.8 (5) |
C6—C7—C8—C9 | −1.1 (6) | C27—C28—C29—C30 | −0.3 (5) |
C7—C8—C9—C10 | 0.4 (6) | C28—C29—C30—C31 | 0.9 (5) |
C8—C9—C10—C5 | −0.3 (6) | C29—C30—C31—C26 | −0.4 (5) |
C6—C5—C10—C9 | 0.9 (5) | C27—C26—C31—C30 | −0.7 (5) |
C4—C5—C10—C9 | 179.2 (3) | C25—C26—C31—C30 | 178.7 (3) |
O1—C4—C11—C12 | 5.6 (4) | O2—C25—C32—C33 | −140.8 (3) |
C3—C4—C11—C12 | −116.3 (3) | C24—C25—C32—C33 | −17.5 (4) |
C5—C4—C11—C12 | 121.9 (3) | C26—C25—C32—C33 | 103.1 (3) |
O1—C4—C11—C16 | −175.6 (2) | O2—C25—C32—C37 | 39.8 (4) |
C3—C4—C11—C16 | 62.5 (4) | C24—C25—C32—C37 | 163.1 (3) |
C5—C4—C11—C16 | −59.3 (4) | C26—C25—C32—C37 | −76.3 (3) |
C16—C11—C12—C13 | 1.1 (5) | C37—C32—C33—C34 | −0.7 (5) |
C4—C11—C12—C13 | 179.9 (3) | C25—C32—C33—C34 | 179.9 (3) |
C11—C12—C13—C14 | −0.5 (5) | C32—C33—C34—C35 | −0.8 (6) |
C12—C13—C14—C15 | 0.2 (6) | C33—C34—C35—C36 | 2.3 (6) |
C13—C14—C15—C16 | −0.5 (6) | C34—C35—C36—C37 | −2.2 (6) |
C14—C15—C16—C11 | 1.2 (5) | C33—C32—C37—C36 | 0.8 (5) |
C12—C11—C16—C15 | −1.4 (5) | C25—C32—C37—C36 | −179.7 (3) |
C4—C11—C16—C15 | 179.7 (3) | C35—C36—C37—C32 | 0.6 (6) |
C4—C3—C17—C18 | 7.9 (5) | C22—C23—C38—C40 | −5.2 (5) |
C2—C3—C17—C18 | −109.3 (4) | C24—C23—C38—C40 | 111.2 (3) |
C4—C3—C17—C19 | −134.4 (3) | C22—C23—C38—C39 | 137.1 (3) |
C2—C3—C17—C19 | 108.3 (3) | C24—C23—C38—C39 | −106.6 (3) |
C4—C3—C17—C2 | 117.3 (4) | C22—C23—C38—C24 | −116.3 (3) |
C1—C2—C17—C18 | −3.7 (4) | C25—C24—C38—C40 | 4.5 (5) |
C3—C2—C17—C18 | 111.0 (3) | C23—C24—C38—C40 | −109.7 (3) |
C1—C2—C17—C19 | 138.9 (3) | C25—C24—C38—C39 | −139.2 (3) |
C3—C2—C17—C19 | −106.4 (3) | C23—C24—C38—C39 | 106.6 (3) |
C1—C2—C17—C3 | −114.7 (3) | C25—C24—C38—C23 | 114.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—HO1···N1 | 0.98 (4) | 1.88 (4) | 2.782 (4) | 152 (3) |
O2—HO2···N2 | 0.90 (4) | 1.86 (4) | 2.716 (4) | 157 (3) |