Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001523/fl2092sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001523/fl2092Isup2.hkl |
CCDC reference: 636633
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.047
- wR factor = 0.150
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT412_ALERT_2_B Short Intra XH3 .. XHn H12B .. H13A .. 1.79 Ang.
Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 15.09 Cell volume su given = 12.00 PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.00 Sigma PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.31 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.96 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT391_ALERT_3_C Deviating Methyl C28 H-C-H Bond Angle ...... 101.00 Deg. PLAT391_ALERT_3_C Deviating Methyl C28 H-C-H Bond Angle ...... 118.00 Deg. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 44.10 Deg. C13B -N2 -C13A 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C14H22N2O | F(000) = 1024 |
Mr = 234.34 | Dx = 1.094 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 12697 reflections |
a = 12.9590 (3) Å | θ = 4.0–68.2° |
b = 13.8003 (3) Å | µ = 0.54 mm−1 |
c = 18.8288 (5) Å | T = 173 K |
β = 122.340 (3)° | Elongated prism, colourless |
V = 2845.00 (12) Å3 | 0.65 × 0.2 × 0.2 mm |
Z = 8 |
Oxford Excalibur PX Ultra CCD area-detector diffractometer | 5218 independent reflections |
Radiation source: fine-focus sealed tube | 3547 reflections with I > 2σ(I) |
Oxford Enhance ULTRA assembly monochromator | Rint = 0.052 |
Detector resolution: 8.1241 pixels mm-1 | θmax = 68.2°, θmin = 4.0° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2006) | k = −16→16 |
Tmin = 0.763, Tmax = 0.897 | l = −22→19 |
34455 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0974P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
5218 reflections | Δρmax = 0.29 e Å−3 |
433 parameters | Δρmin = −0.24 e Å−3 |
6 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0015 (5) |
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 | Occ. (<1) | |
C1 | 0.15671 (15) | 0.26110 (12) | 0.54100 (9) | 0.0456 (4) | |
C2 | 0.10636 (16) | 0.35046 (12) | 0.50453 (10) | 0.0499 (4) | |
C3 | 0.1864 (2) | 0.43133 (15) | 0.50737 (14) | 0.0644 (5) | |
H3A | 0.249 (2) | 0.4552 (19) | 0.5693 (16) | 0.097* | |
H3B | 0.139 (2) | 0.488 (2) | 0.4739 (16) | 0.097* | |
H3C | 0.233 (2) | 0.4109 (19) | 0.4835 (16) | 0.097* | |
C4 | −0.01866 (17) | 0.36272 (15) | 0.46631 (10) | 0.0565 (5) | |
H4 | −0.0564 (19) | 0.4283 (15) | 0.4411 (13) | 0.068* | |
C5 | −0.09076 (19) | 0.28902 (16) | 0.46509 (11) | 0.0623 (5) | |
H5 | −0.176 (2) | 0.3027 (16) | 0.4401 (14) | 0.075* | |
C6 | −0.03930 (19) | 0.20077 (17) | 0.50129 (12) | 0.0631 (5) | |
H6 | −0.087 (2) | 0.1522 (17) | 0.5007 (13) | 0.076* | |
C7 | 0.08543 (17) | 0.18487 (13) | 0.53983 (11) | 0.0538 (4) | |
C8 | 0.1418 (2) | 0.08855 (17) | 0.57887 (17) | 0.0738 (6) | |
H8A | 0.208 (3) | 0.104 (2) | 0.6339 (19) | 0.111* | |
H8B | 0.080 (3) | 0.044 (2) | 0.5824 (17) | 0.111* | |
H8C | 0.164 (3) | 0.050 (2) | 0.5439 (18) | 0.111* | |
N1 | 0.28542 (13) | 0.24867 (10) | 0.58133 (8) | 0.0475 (3) | |
H1N | 0.3324 (19) | 0.2760 (14) | 0.6283 (13) | 0.057* | |
C9 | 0.33741 (15) | 0.20074 (12) | 0.54664 (9) | 0.0456 (4) | |
O1 | 0.27929 (12) | 0.15840 (10) | 0.47863 (7) | 0.0626 (4) | |
C10 | 0.47476 (17) | 0.20231 (16) | 0.59600 (11) | 0.0543 (4) | |
H10A | 0.5049 (19) | 0.1354 (16) | 0.6056 (12) | 0.065* | |
H10B | 0.502 (2) | 0.2338 (14) | 0.5624 (13) | 0.065* | |
N2 | 0.52983 (13) | 0.25150 (10) | 0.67615 (8) | 0.0515 (4) | |
C11 | 0.6027 (3) | 0.3329 (2) | 0.6818 (2) | 0.1123 (11) | |
H11A | 0.5592 | 0.3692 | 0.6282 | 0.135* | |
H11B | 0.6806 | 0.3092 | 0.6902 | 0.135* | |
C12 | 0.6296 (4) | 0.3999 (3) | 0.7527 (3) | 0.1510 (17) | |
H12A | 0.6687 | 0.4589 | 0.7492 | 0.226* | |
H12B | 0.6845 | 0.3676 | 0.8065 | 0.226* | |
H12C | 0.5532 | 0.4169 | 0.7487 | 0.226* | |
C13A | 0.6300 (4) | 0.1952 (3) | 0.7466 (2) | 0.0666 (15) | 0.512 (7) |
H13A | 0.6821 | 0.2385 | 0.7948 | 0.080* | 0.512 (7) |
H13B | 0.6814 | 0.1646 | 0.7286 | 0.080* | 0.512 (7) |
C14A | 0.5729 (9) | 0.1186 (5) | 0.7720 (4) | 0.107 (3) | 0.512 (7) |
H14A | 0.6372 | 0.0823 | 0.8202 | 0.161* | 0.512 (7) |
H14B | 0.5248 | 0.0742 | 0.7248 | 0.161* | 0.512 (7) |
H14C | 0.5195 | 0.1494 | 0.7874 | 0.161* | 0.512 (7) |
C13B | 0.5404 (4) | 0.1832 (3) | 0.7401 (2) | 0.0608 (15) | 0.488 (7) |
H13C | 0.4627 | 0.1473 | 0.7166 | 0.073* | 0.488 (7) |
H13D | 0.5540 | 0.2203 | 0.7894 | 0.073* | 0.488 (7) |
C14B | 0.6424 (5) | 0.1124 (5) | 0.7681 (3) | 0.087 (2) | 0.488 (7) |
H14D | 0.6455 | 0.0687 | 0.8102 | 0.131* | 0.488 (7) |
H14E | 0.7200 | 0.1475 | 0.7928 | 0.131* | 0.488 (7) |
H14F | 0.6287 | 0.0746 | 0.7197 | 0.131* | 0.488 (7) |
C15 | 0.41740 (15) | 0.23171 (12) | 0.38461 (9) | 0.0450 (4) | |
C16 | 0.53186 (16) | 0.18730 (13) | 0.42800 (10) | 0.0500 (4) | |
C17 | 0.5440 (2) | 0.08044 (16) | 0.42437 (14) | 0.0667 (5) | |
H17A | 0.518 (2) | 0.0584 (19) | 0.3647 (18) | 0.100* | |
H17B | 0.622 (3) | 0.057 (2) | 0.4606 (18) | 0.100* | |
H17C | 0.493 (3) | 0.043 (2) | 0.4381 (17) | 0.100* | |
C18 | 0.63408 (19) | 0.24638 (16) | 0.47592 (12) | 0.0620 (5) | |
H18 | 0.710 (2) | 0.2162 (16) | 0.5054 (14) | 0.074* | |
C19 | 0.6225 (2) | 0.34411 (17) | 0.48077 (14) | 0.0710 (6) | |
H19 | 0.690 (2) | 0.3808 (18) | 0.5093 (15) | 0.085* | |
C20 | 0.5087 (2) | 0.38660 (16) | 0.43738 (14) | 0.0721 (6) | |
H20 | 0.504 (2) | 0.4551 (19) | 0.4432 (15) | 0.087* | |
C21 | 0.40342 (18) | 0.33134 (13) | 0.38851 (11) | 0.0569 (5) | |
C22 | 0.2787 (2) | 0.3761 (2) | 0.34170 (17) | 0.0798 (6) | |
H22A | 0.215 (3) | 0.343 (2) | 0.3521 (19) | 0.120* | |
H22B | 0.283 (3) | 0.447 (3) | 0.3518 (18) | 0.120* | |
H22C | 0.247 (3) | 0.366 (2) | 0.285 (2) | 0.120* | |
N3 | 0.31060 (13) | 0.17385 (10) | 0.33790 (8) | 0.0475 (3) | |
H3N | 0.2676 (18) | 0.1613 (14) | 0.3609 (12) | 0.057* | |
C23 | 0.27214 (16) | 0.13607 (12) | 0.26209 (9) | 0.0482 (4) | |
O2 | 0.32684 (12) | 0.14519 (10) | 0.22571 (7) | 0.0617 (4) | |
C24 | 0.15472 (19) | 0.07774 (16) | 0.22338 (11) | 0.0603 (5) | |
H24A | 0.110 (2) | 0.0974 (15) | 0.1637 (14) | 0.072* | |
H24B | 0.1781 (19) | 0.0103 (17) | 0.2257 (13) | 0.072* | |
N4 | 0.08903 (13) | 0.08973 (11) | 0.26510 (8) | 0.0561 (4) | |
C25 | 0.0375 (2) | −0.00111 (18) | 0.27340 (14) | 0.0752 (6) | |
H25A | 0.003 (2) | −0.0423 (18) | 0.2210 (16) | 0.090* | |
H25B | −0.032 (2) | 0.0187 (18) | 0.2828 (15) | 0.090* | |
C26 | 0.1318 (3) | −0.0596 (2) | 0.34719 (17) | 0.0943 (9) | |
H26A | 0.161 (3) | −0.020 (3) | 0.398 (2) | 0.141* | |
H26B | 0.101 (3) | −0.122 (3) | 0.358 (2) | 0.141* | |
H26C | 0.205 (3) | −0.074 (2) | 0.339 (2) | 0.141* | |
C27 | 0.0012 (2) | 0.1701 (2) | 0.23025 (14) | 0.0779 (6) | |
H27A | −0.072 (2) | 0.1473 (18) | 0.1716 (17) | 0.094* | |
H27B | 0.044 (2) | 0.2244 (19) | 0.2136 (16) | 0.094* | |
C28 | −0.0307 (3) | 0.2088 (3) | 0.2911 (2) | 0.0973 (8) | |
H28A | −0.092 (4) | 0.267 (3) | 0.262 (2) | 0.146* | |
H28B | −0.087 (4) | 0.158 (3) | 0.296 (2) | 0.146* | |
H28C | 0.052 (4) | 0.229 (3) | 0.347 (2) | 0.146* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0438 (9) | 0.0542 (9) | 0.0381 (7) | −0.0009 (7) | 0.0214 (7) | −0.0029 (7) |
C2 | 0.0544 (10) | 0.0546 (10) | 0.0414 (8) | 0.0003 (8) | 0.0261 (8) | −0.0029 (7) |
C3 | 0.0713 (14) | 0.0555 (11) | 0.0691 (12) | −0.0055 (10) | 0.0394 (11) | 0.0005 (9) |
C4 | 0.0557 (11) | 0.0637 (11) | 0.0457 (9) | 0.0076 (9) | 0.0241 (8) | 0.0027 (8) |
C5 | 0.0478 (11) | 0.0838 (14) | 0.0517 (10) | 0.0044 (10) | 0.0241 (9) | 0.0018 (9) |
C6 | 0.0532 (12) | 0.0750 (13) | 0.0641 (11) | −0.0103 (10) | 0.0332 (9) | −0.0004 (10) |
C7 | 0.0533 (11) | 0.0581 (10) | 0.0518 (9) | −0.0020 (8) | 0.0293 (8) | 0.0010 (8) |
C8 | 0.0744 (15) | 0.0604 (13) | 0.0903 (15) | −0.0004 (11) | 0.0467 (12) | 0.0130 (12) |
N1 | 0.0437 (8) | 0.0578 (8) | 0.0388 (6) | −0.0030 (6) | 0.0207 (6) | −0.0096 (6) |
C9 | 0.0491 (9) | 0.0515 (9) | 0.0374 (7) | −0.0033 (7) | 0.0239 (7) | −0.0043 (7) |
O1 | 0.0562 (8) | 0.0858 (9) | 0.0469 (6) | −0.0128 (6) | 0.0283 (6) | −0.0220 (6) |
C10 | 0.0509 (10) | 0.0668 (12) | 0.0475 (9) | −0.0021 (9) | 0.0279 (8) | −0.0107 (8) |
N2 | 0.0505 (9) | 0.0533 (8) | 0.0406 (7) | −0.0013 (6) | 0.0177 (6) | −0.0056 (6) |
C11 | 0.126 (2) | 0.112 (2) | 0.144 (3) | −0.0615 (19) | 0.102 (2) | −0.0683 (19) |
C12 | 0.210 (4) | 0.119 (2) | 0.194 (4) | −0.096 (3) | 0.155 (3) | −0.100 (3) |
C13A | 0.067 (3) | 0.060 (3) | 0.050 (2) | 0.007 (2) | 0.0160 (19) | 0.0060 (17) |
C14A | 0.196 (9) | 0.063 (4) | 0.097 (4) | −0.001 (5) | 0.102 (6) | 0.007 (3) |
C13B | 0.056 (3) | 0.071 (3) | 0.048 (2) | 0.000 (2) | 0.0227 (19) | −0.005 (2) |
C14B | 0.078 (4) | 0.080 (4) | 0.054 (3) | 0.022 (3) | 0.003 (2) | −0.008 (3) |
C15 | 0.0444 (9) | 0.0511 (9) | 0.0409 (8) | −0.0049 (7) | 0.0238 (7) | −0.0012 (7) |
C16 | 0.0475 (10) | 0.0601 (10) | 0.0443 (8) | −0.0018 (8) | 0.0258 (7) | 0.0042 (7) |
C17 | 0.0685 (14) | 0.0639 (13) | 0.0613 (11) | 0.0127 (10) | 0.0306 (10) | 0.0076 (9) |
C18 | 0.0449 (11) | 0.0835 (15) | 0.0553 (10) | −0.0080 (9) | 0.0252 (9) | 0.0068 (9) |
C19 | 0.0589 (13) | 0.0768 (15) | 0.0649 (12) | −0.0259 (11) | 0.0247 (10) | −0.0033 (10) |
C20 | 0.0816 (16) | 0.0513 (11) | 0.0735 (13) | −0.0144 (11) | 0.0348 (12) | −0.0078 (10) |
C21 | 0.0595 (11) | 0.0541 (10) | 0.0541 (9) | −0.0006 (8) | 0.0284 (9) | 0.0005 (8) |
C22 | 0.0757 (16) | 0.0687 (14) | 0.0803 (14) | 0.0179 (12) | 0.0318 (13) | 0.0009 (12) |
N3 | 0.0465 (8) | 0.0575 (8) | 0.0411 (7) | −0.0102 (6) | 0.0251 (6) | −0.0044 (6) |
C23 | 0.0542 (10) | 0.0518 (9) | 0.0382 (8) | 0.0006 (7) | 0.0244 (7) | 0.0048 (7) |
O2 | 0.0650 (8) | 0.0828 (9) | 0.0437 (6) | −0.0031 (7) | 0.0333 (6) | 0.0053 (6) |
C24 | 0.0639 (12) | 0.0694 (12) | 0.0434 (9) | −0.0144 (10) | 0.0261 (8) | −0.0091 (9) |
N4 | 0.0469 (8) | 0.0696 (10) | 0.0449 (7) | −0.0125 (7) | 0.0199 (6) | −0.0005 (7) |
C25 | 0.0693 (14) | 0.0842 (15) | 0.0646 (12) | −0.0299 (12) | 0.0309 (11) | −0.0064 (11) |
C26 | 0.118 (2) | 0.0832 (17) | 0.0694 (14) | −0.0216 (16) | 0.0417 (15) | 0.0085 (12) |
C27 | 0.0580 (13) | 0.0978 (17) | 0.0643 (12) | 0.0056 (12) | 0.0235 (10) | 0.0148 (12) |
C28 | 0.0664 (16) | 0.129 (2) | 0.0957 (18) | 0.0241 (16) | 0.0425 (14) | 0.0106 (17) |
C1—C2 | 1.392 (2) | C14B—H14D | 0.9800 |
C1—C7 | 1.392 (2) | C14B—H14E | 0.9800 |
C1—N1 | 1.426 (2) | C14B—H14F | 0.9800 |
C2—C4 | 1.387 (3) | C15—C21 | 1.394 (3) |
C2—C3 | 1.505 (3) | C15—C16 | 1.395 (2) |
C3—H3A | 1.06 (3) | C15—N3 | 1.423 (2) |
C3—H3B | 0.99 (3) | C16—C18 | 1.398 (3) |
C3—H3C | 0.97 (3) | C16—C17 | 1.488 (3) |
C4—C5 | 1.373 (3) | C17—H17A | 1.03 (3) |
C4—H4 | 1.02 (2) | C17—H17B | 0.92 (3) |
C5—C6 | 1.381 (3) | C17—H17C | 0.98 (3) |
C5—H5 | 0.96 (2) | C18—C19 | 1.366 (3) |
C6—C7 | 1.390 (3) | C18—H18 | 0.93 (2) |
C6—H6 | 0.91 (2) | C19—C20 | 1.377 (3) |
C7—C8 | 1.506 (3) | C19—H19 | 0.90 (3) |
C8—H8A | 0.95 (3) | C20—C21 | 1.395 (3) |
C8—H8B | 1.04 (3) | C20—H20 | 0.96 (3) |
C8—H8C | 1.01 (3) | C21—C22 | 1.499 (3) |
N1—C9 | 1.338 (2) | C22—H22A | 1.05 (3) |
N1—H1N | 0.85 (2) | C22—H22B | 1.00 (3) |
C9—O1 | 1.2314 (19) | C22—H22C | 0.92 (3) |
C9—C10 | 1.504 (3) | N3—C23 | 1.340 (2) |
C10—N2 | 1.447 (2) | N3—H3N | 0.89 (2) |
C10—H10A | 0.98 (2) | C23—O2 | 1.228 (2) |
C10—H10B | 0.97 (2) | C23—C24 | 1.519 (3) |
N2—C11 | 1.434 (3) | C24—N4 | 1.444 (2) |
N2—C13B | 1.476 (4) | C24—H24A | 0.99 (2) |
N2—C13A | 1.486 (4) | C24—H24B | 0.97 (2) |
C11—C12 | 1.504 (3) | N4—C25 | 1.468 (3) |
C11—H11A | 0.9900 | N4—C27 | 1.469 (3) |
C11—H11B | 0.9900 | C25—C26 | 1.503 (4) |
C12—H12A | 0.9800 | C25—H25A | 1.01 (3) |
C12—H12B | 0.9800 | C25—H25B | 1.04 (3) |
C12—H12C | 0.9800 | C26—H26A | 0.99 (4) |
C13A—C14A | 1.507 (5) | C26—H26B | 1.02 (4) |
C13A—H13A | 0.9900 | C26—H26C | 1.06 (4) |
C13A—H13B | 0.9900 | C27—C28 | 1.508 (4) |
C14A—H14A | 0.9800 | C27—H27A | 1.05 (3) |
C14A—H14B | 0.9800 | C27—H27B | 1.08 (3) |
C14A—H14C | 0.9800 | C28—H28A | 1.06 (4) |
C13B—C14B | 1.495 (5) | C28—H28B | 1.05 (4) |
C13B—H13C | 0.9900 | C28—H28C | 1.06 (4) |
C13B—H13D | 0.9900 | ||
C2—C1—C7 | 121.97 (16) | H14D—C14B—H14E | 109.5 |
C2—C1—N1 | 118.38 (15) | C13B—C14B—H14F | 109.5 |
C7—C1—N1 | 119.65 (15) | H14D—C14B—H14F | 109.5 |
C4—C2—C1 | 118.24 (17) | H14E—C14B—H14F | 109.5 |
C4—C2—C3 | 121.30 (18) | C21—C15—C16 | 122.00 (16) |
C1—C2—C3 | 120.46 (17) | C21—C15—N3 | 118.38 (15) |
C2—C3—H3A | 112.5 (14) | C16—C15—N3 | 119.55 (15) |
C2—C3—H3B | 112.7 (15) | C15—C16—C18 | 117.72 (18) |
H3A—C3—H3B | 108 (2) | C15—C16—C17 | 120.90 (17) |
C2—C3—H3C | 110.9 (16) | C18—C16—C17 | 121.38 (18) |
H3A—C3—H3C | 107 (2) | C16—C17—H17A | 111.2 (14) |
H3B—C3—H3C | 105 (2) | C16—C17—H17B | 114.1 (17) |
C5—C4—C2 | 120.93 (19) | H17A—C17—H17B | 107 (2) |
C5—C4—H4 | 119.9 (12) | C16—C17—H17C | 113.8 (16) |
C2—C4—H4 | 119.1 (12) | H17A—C17—H17C | 105 (2) |
C4—C5—C6 | 120.03 (19) | H17B—C17—H17C | 105 (2) |
C4—C5—H5 | 117.2 (14) | C19—C18—C16 | 121.3 (2) |
C6—C5—H5 | 122.8 (14) | C19—C18—H18 | 121.4 (14) |
C5—C6—C7 | 121.1 (2) | C16—C18—H18 | 117.3 (14) |
C5—C6—H6 | 119.8 (15) | C18—C19—C20 | 120.2 (2) |
C7—C6—H6 | 119.1 (14) | C18—C19—H19 | 119.1 (16) |
C6—C7—C1 | 117.72 (18) | C20—C19—H19 | 120.5 (16) |
C6—C7—C8 | 121.29 (19) | C19—C20—C21 | 121.2 (2) |
C1—C7—C8 | 120.98 (18) | C19—C20—H20 | 117.5 (15) |
C7—C8—H8A | 104.8 (19) | C21—C20—H20 | 121.3 (15) |
C7—C8—H8B | 111.1 (16) | C15—C21—C20 | 117.71 (18) |
H8A—C8—H8B | 110 (2) | C15—C21—C22 | 120.35 (18) |
C7—C8—H8C | 112.6 (17) | C20—C21—C22 | 121.9 (2) |
H8A—C8—H8C | 115 (3) | C21—C22—H22A | 114.5 (17) |
H8B—C8—H8C | 104 (2) | C21—C22—H22B | 111.3 (18) |
C9—N1—C1 | 123.42 (14) | H22A—C22—H22B | 111 (2) |
C9—N1—H1N | 117.5 (14) | C21—C22—H22C | 107 (2) |
C1—N1—H1N | 118.9 (14) | H22A—C22—H22C | 104 (3) |
O1—C9—N1 | 123.69 (16) | H22B—C22—H22C | 109 (3) |
O1—C9—C10 | 120.85 (14) | C23—N3—C15 | 124.13 (14) |
N1—C9—C10 | 115.46 (14) | C23—N3—H3N | 118.1 (12) |
N2—C10—C9 | 114.30 (14) | C15—N3—H3N | 117.7 (12) |
N2—C10—H10A | 108.9 (12) | O2—C23—N3 | 123.88 (16) |
C9—C10—H10A | 108.9 (12) | O2—C23—C24 | 121.05 (15) |
N2—C10—H10B | 108.6 (12) | N3—C23—C24 | 115.05 (15) |
C9—C10—H10B | 108.9 (13) | N4—C24—C23 | 114.14 (14) |
H10A—C10—H10B | 107.0 (17) | N4—C24—H24A | 115.5 (12) |
C11—N2—C10 | 112.48 (17) | C23—C24—H24A | 103.1 (12) |
C11—N2—C13B | 132.0 (2) | N4—C24—H24B | 110.2 (13) |
C10—N2—C13B | 109.3 (2) | C23—C24—H24B | 106.1 (13) |
C11—N2—C13A | 96.7 (3) | H24A—C24—H24B | 107.0 (18) |
C10—N2—C13A | 113.2 (2) | C24—N4—C25 | 113.23 (18) |
C13B—N2—C13A | 44.1 (2) | C24—N4—C27 | 112.65 (16) |
N2—C11—C12 | 112.2 (2) | C25—N4—C27 | 113.86 (18) |
N2—C11—H11A | 109.2 | N4—C25—C26 | 111.47 (19) |
C12—C11—H11A | 109.2 | N4—C25—H25A | 111.4 (14) |
N2—C11—H11B | 109.2 | C26—C25—H25A | 108.4 (14) |
C12—C11—H11B | 109.2 | N4—C25—H25B | 106.1 (14) |
H11A—C11—H11B | 107.9 | C26—C25—H25B | 109.4 (14) |
C11—C12—H12A | 109.5 | H25A—C25—H25B | 110 (2) |
C11—C12—H12B | 109.5 | C25—C26—H26A | 107 (2) |
H12A—C12—H12B | 109.5 | C25—C26—H26B | 116 (2) |
C11—C12—H12C | 109.5 | H26A—C26—H26B | 105 (3) |
H12A—C12—H12C | 109.5 | C25—C26—H26C | 108.1 (19) |
H12B—C12—H12C | 109.5 | H26A—C26—H26C | 110 (3) |
N2—C13A—C14A | 107.9 (5) | H26B—C26—H26C | 111 (3) |
N2—C13A—H13A | 110.1 | N4—C27—C28 | 112.9 (2) |
C14A—C13A—H13A | 110.1 | N4—C27—H27A | 106.9 (14) |
N2—C13A—H13B | 110.1 | C28—C27—H27A | 116.7 (14) |
C14A—C13A—H13B | 110.1 | N4—C27—H27B | 104.9 (14) |
H13A—C13A—H13B | 108.4 | C28—C27—H27B | 111.7 (14) |
N2—C13B—C14B | 112.6 (4) | H27A—C27—H27B | 102.6 (19) |
N2—C13B—H13C | 109.1 | C27—C28—H28A | 108 (2) |
C14B—C13B—H13C | 109.1 | C27—C28—H28B | 108 (2) |
N2—C13B—H13D | 109.1 | H28A—C28—H28B | 101 (3) |
C14B—C13B—H13D | 109.1 | C27—C28—H28C | 107 (2) |
H13C—C13B—H13D | 107.8 | H28A—C28—H28C | 114 (3) |
C13B—C14B—H14D | 109.5 | H28B—C28—H28C | 118 (3) |
C13B—C14B—H14E | 109.5 | ||
C7—C1—C2—C4 | 0.1 (2) | C11—N2—C13B—C14B | −73.6 (4) |
N1—C1—C2—C4 | −179.17 (14) | C10—N2—C13B—C14B | 75.7 (4) |
C7—C1—C2—C3 | 179.73 (16) | C13A—N2—C13B—C14B | −28.1 (4) |
N1—C1—C2—C3 | 0.4 (2) | C21—C15—C16—C18 | −0.4 (2) |
C1—C2—C4—C5 | 0.6 (2) | N3—C15—C16—C18 | −177.41 (14) |
C3—C2—C4—C5 | −179.03 (18) | C21—C15—C16—C17 | 178.53 (17) |
C2—C4—C5—C6 | −0.8 (3) | N3—C15—C16—C17 | 1.5 (2) |
C4—C5—C6—C7 | 0.4 (3) | C15—C16—C18—C19 | 0.5 (3) |
C5—C6—C7—C1 | 0.3 (3) | C17—C16—C18—C19 | −178.40 (19) |
C5—C6—C7—C8 | −179.6 (2) | C16—C18—C19—C20 | −0.6 (3) |
C2—C1—C7—C6 | −0.5 (2) | C18—C19—C20—C21 | 0.6 (3) |
N1—C1—C7—C6 | 178.75 (15) | C16—C15—C21—C20 | 0.4 (3) |
C2—C1—C7—C8 | 179.32 (18) | N3—C15—C21—C20 | 177.41 (16) |
N1—C1—C7—C8 | −1.4 (3) | C16—C15—C21—C22 | −179.32 (18) |
C2—C1—N1—C9 | −102.67 (19) | N3—C15—C21—C22 | −2.3 (3) |
C7—C1—N1—C9 | 78.0 (2) | C19—C20—C21—C15 | −0.5 (3) |
C1—N1—C9—O1 | −4.0 (3) | C19—C20—C21—C22 | 179.2 (2) |
C1—N1—C9—C10 | 175.29 (16) | C21—C15—N3—C23 | 104.99 (19) |
O1—C9—C10—N2 | −177.58 (16) | C16—C15—N3—C23 | −77.9 (2) |
N1—C9—C10—N2 | 3.1 (2) | C15—N3—C23—O2 | 2.0 (3) |
C9—C10—N2—C11 | −119.5 (2) | C15—N3—C23—C24 | −179.22 (16) |
C9—C10—N2—C13B | 84.8 (3) | O2—C23—C24—N4 | −168.24 (17) |
C9—C10—N2—C13A | 132.1 (2) | N3—C23—C24—N4 | 13.0 (2) |
C10—N2—C11—C12 | 163.5 (3) | C23—C24—N4—C25 | −139.36 (17) |
C13B—N2—C11—C12 | −48.0 (5) | C23—C24—N4—C27 | 89.6 (2) |
C13A—N2—C11—C12 | −77.9 (3) | C24—N4—C25—C26 | 81.4 (2) |
C11—N2—C13A—C14A | 163.3 (4) | C27—N4—C25—C26 | −148.2 (2) |
C10—N2—C13A—C14A | −78.7 (4) | C24—N4—C27—C28 | −157.4 (2) |
C13B—N2—C13A—C14A | 15.5 (3) | C25—N4—C27—C28 | 71.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O1 | 0.89 (2) | 2.14 (2) | 2.8952 (18) | 142.6 (17) |
N1—H1N···O2i | 0.85 (2) | 2.17 (2) | 2.8746 (17) | 140.9 (18) |
N1—H1N···N2 | 0.85 (2) | 2.24 (2) | 2.678 (2) | 112.3 (16) |
N3—H3N···N4 | 0.89 (2) | 2.262 (19) | 2.695 (2) | 109.7 (15) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
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