Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806027814/rz2060sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806027814/rz2060Isup2.hkl |
CCDC reference: 618314
Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
C14H11N3OS | F(000) = 1120 |
Mr = 269.32 | Dx = 1.361 Mg m−3 |
Monoclinic, P21/c | Melting point: 453 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.2294 (6) Å | Cell parameters from 4683 reflections |
b = 7.5234 (4) Å | θ = 2.2–22.9° |
c = 31.1642 (15) Å | µ = 0.24 mm−1 |
β = 92.824 (1)° | T = 298 K |
V = 2629.7 (2) Å3 | Needle, colourless |
Z = 8 | 0.53 × 0.23 × 0.18 mm |
Bruker SMART APEX-II CCD area-detector diffractometer | 7646 independent reflections |
Radiation source: fine-focus sealed tube | 4375 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 30.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→16 |
Tmin = 0.883, Tmax = 0.958 | k = −8→10 |
25340 measured reflections | l = −42→44 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0502P)2 + 0.2457P] where P = (Fo2 + 2Fc2)/3 |
7646 reflections | (Δ/σ)max = 0.002 |
343 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Experimental. Spectroscopic anlysis: IR (Medium?, ν, cm-1): 3101 (–NH), 1639 (C═N), 853 (–C—S); 1H NMR (DMSO-d6, TMS, δ, p.p.m.): 7.55 (m, 5H, aromatic), 8.23–9.25 (m, 4H, pyridine), 4.12 (s, 2H, methylene); 13C NMR (DMSO-d6, TMS, δ, p.p.m.): 139.24 (C1A), 129.16 (C2A, C6A), 130.29 (C3A, C5A), 121.69 (C4A), 40.38 (C7A), 177.87 (C8A), 164.20 (C9A), 158.97 (C10A), 121.69 (C11A), 150.41 (C12A), 150.04 (C13A), 119.89 (C14A). |
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 | ||
S1A | 0.08343 (4) | 0.10883 (6) | 0.130666 (14) | 0.06755 (15) | |
S1B | 0.56664 (4) | 0.40116 (7) | −0.126358 (15) | 0.07555 (16) | |
O1A | 0.08129 (9) | 0.17239 (14) | 0.04696 (3) | 0.0583 (3) | |
O1B | 0.57684 (9) | 0.32657 (15) | −0.04305 (3) | 0.0608 (3) | |
N1A | 0.22535 (12) | −0.0120 (2) | 0.06859 (5) | 0.0688 (4) | |
N2A | 0.23163 (12) | 0.0163 (2) | 0.02409 (5) | 0.0710 (4) | |
N3A | 0.07025 (18) | 0.3414 (3) | −0.11107 (6) | 0.0901 (5) | |
N1B | 0.71550 (13) | 0.5168 (2) | −0.06099 (5) | 0.0776 (4) | |
N2B | 0.72924 (14) | 0.4821 (2) | −0.01675 (5) | 0.0800 (4) | |
N3B | 0.59414 (18) | 0.1385 (3) | 0.11356 (5) | 0.0928 (5) | |
C1A | 0.15107 (13) | −0.0585 (2) | 0.20516 (5) | 0.0553 (4) | |
C2A | 0.22580 (13) | 0.0152 (2) | 0.23710 (6) | 0.0632 (4) | |
H2AA | 0.2951 | 0.0731 | 0.2298 | 0.076* | |
C3A | 0.19859 (16) | 0.0035 (2) | 0.27955 (6) | 0.0706 (5) | |
H3AA | 0.2494 | 0.0536 | 0.3007 | 0.085* | |
C4A | 0.09702 (16) | −0.0814 (2) | 0.29080 (6) | 0.0686 (5) | |
H4AA | 0.0786 | −0.0889 | 0.3195 | 0.082* | |
C5A | 0.02282 (15) | −0.1552 (2) | 0.25957 (6) | 0.0665 (5) | |
H5AA | −0.0462 | −0.2131 | 0.2672 | 0.080* | |
C6A | 0.04911 (14) | −0.1447 (2) | 0.21704 (6) | 0.0612 (4) | |
H6AA | −0.0020 | −0.1958 | 0.1961 | 0.073* | |
C7A | 0.18135 (16) | −0.0497 (3) | 0.15885 (6) | 0.0747 (5) | |
H7AA | 0.1719 | −0.1661 | 0.1458 | 0.090* | |
H7AB | 0.2637 | −0.0132 | 0.1568 | 0.090* | |
C8A | 0.13694 (14) | 0.0825 (2) | 0.08008 (5) | 0.0578 (4) | |
C9A | 0.14707 (14) | 0.1243 (2) | 0.01300 (5) | 0.0566 (4) | |
C10A | 0.11741 (14) | 0.1980 (2) | −0.02934 (5) | 0.0585 (4) | |
C11A | 0.01883 (15) | 0.3037 (2) | −0.03784 (6) | 0.0673 (4) | |
H11A | −0.0340 | 0.3285 | −0.0166 | 0.081* | |
C12A | 0.00060 (18) | 0.3719 (3) | −0.07876 (7) | 0.0805 (5) | |
H12A | −0.0655 | 0.4446 | −0.0840 | 0.097* | |
C13A | 0.1636 (2) | 0.2372 (3) | −0.10205 (6) | 0.0911 (6) | |
H13A | 0.2136 | 0.2120 | −0.1242 | 0.109* | |
C14A | 0.19158 (17) | 0.1642 (3) | −0.06265 (6) | 0.0761 (5) | |
H14A | 0.2590 | 0.0934 | −0.0583 | 0.091* | |
C1B | 0.63732 (14) | 0.5699 (2) | −0.19808 (6) | 0.0610 (4) | |
C2B | 0.72168 (15) | 0.4992 (2) | −0.22394 (7) | 0.0754 (5) | |
H2BA | 0.7905 | 0.4480 | −0.2116 | 0.091* | |
C3B | 0.70437 (19) | 0.5042 (3) | −0.26805 (8) | 0.0886 (6) | |
H3BA | 0.7611 | 0.4559 | −0.2854 | 0.106* | |
C4B | 0.6026 (2) | 0.5812 (3) | −0.28619 (7) | 0.0839 (6) | |
H4BA | 0.5903 | 0.5849 | −0.3159 | 0.101* | |
C5B | 0.52020 (17) | 0.6516 (3) | −0.26067 (7) | 0.0778 (5) | |
H5BA | 0.4519 | 0.7044 | −0.2730 | 0.093* | |
C6B | 0.53710 (14) | 0.6453 (2) | −0.21723 (6) | 0.0683 (5) | |
H6BA | 0.4795 | 0.6930 | −0.2001 | 0.082* | |
C7B | 0.65897 (19) | 0.5695 (3) | −0.15037 (6) | 0.0889 (6) | |
H7BA | 0.6402 | 0.6855 | −0.1389 | 0.107* | |
H7BB | 0.7424 | 0.5449 | −0.1432 | 0.107* | |
C8B | 0.62646 (14) | 0.4219 (2) | −0.07447 (6) | 0.0621 (4) | |
C9B | 0.64745 (14) | 0.3709 (2) | −0.00774 (5) | 0.0608 (4) | |
C10B | 0.62597 (14) | 0.2915 (2) | 0.03365 (5) | 0.0615 (4) | |
C11B | 0.52904 (15) | 0.1844 (2) | 0.04028 (6) | 0.0667 (4) | |
H11B | 0.4724 | 0.1622 | 0.0182 | 0.080* | |
C12B | 0.51782 (18) | 0.1110 (3) | 0.08041 (6) | 0.0793 (5) | |
H12B | 0.4527 | 0.0376 | 0.0845 | 0.095* | |
C13B | 0.6863 (2) | 0.2432 (3) | 0.10664 (7) | 0.0981 (7) | |
H13B | 0.7410 | 0.2643 | 0.1295 | 0.118* | |
C14B | 0.70610 (18) | 0.3222 (3) | 0.06803 (6) | 0.0821 (6) | |
H14B | 0.7721 | 0.3950 | 0.0650 | 0.099* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0709 (3) | 0.0669 (3) | 0.0659 (3) | 0.0126 (2) | 0.0137 (2) | 0.0033 (2) |
S1B | 0.0810 (3) | 0.0711 (3) | 0.0737 (3) | −0.0193 (2) | −0.0047 (2) | 0.0078 (2) |
O1A | 0.0576 (6) | 0.0559 (7) | 0.0616 (6) | 0.0025 (5) | 0.0060 (5) | −0.0027 (5) |
O1B | 0.0593 (6) | 0.0560 (7) | 0.0669 (7) | −0.0081 (5) | −0.0012 (5) | −0.0024 (5) |
N1A | 0.0687 (8) | 0.0705 (10) | 0.0679 (9) | 0.0124 (7) | 0.0110 (7) | 0.0006 (7) |
N2A | 0.0736 (9) | 0.0721 (10) | 0.0682 (9) | 0.0133 (8) | 0.0123 (7) | −0.0024 (7) |
N3A | 0.1150 (14) | 0.0852 (13) | 0.0693 (10) | −0.0045 (11) | −0.0050 (10) | 0.0023 (9) |
N1B | 0.0776 (9) | 0.0722 (11) | 0.0822 (11) | −0.0224 (8) | −0.0027 (8) | −0.0006 (8) |
N2B | 0.0798 (10) | 0.0760 (11) | 0.0832 (11) | −0.0232 (9) | −0.0046 (8) | −0.0078 (8) |
N3B | 0.1109 (14) | 0.1002 (15) | 0.0675 (11) | −0.0031 (11) | 0.0059 (10) | −0.0045 (9) |
C1A | 0.0549 (8) | 0.0441 (9) | 0.0672 (10) | 0.0081 (7) | 0.0057 (7) | 0.0045 (7) |
C2A | 0.0484 (8) | 0.0480 (10) | 0.0927 (13) | −0.0037 (7) | −0.0008 (8) | 0.0110 (9) |
C3A | 0.0764 (11) | 0.0578 (11) | 0.0752 (12) | −0.0021 (9) | −0.0183 (9) | 0.0026 (9) |
C4A | 0.0796 (11) | 0.0601 (11) | 0.0665 (11) | 0.0079 (9) | 0.0076 (9) | 0.0073 (8) |
C5A | 0.0569 (9) | 0.0593 (11) | 0.0840 (12) | −0.0030 (8) | 0.0102 (9) | 0.0093 (9) |
C6A | 0.0586 (9) | 0.0514 (10) | 0.0731 (11) | −0.0059 (7) | −0.0023 (8) | −0.0013 (8) |
C7A | 0.0775 (11) | 0.0691 (12) | 0.0789 (12) | 0.0201 (9) | 0.0173 (9) | 0.0093 (9) |
C8A | 0.0574 (8) | 0.0515 (10) | 0.0648 (10) | −0.0028 (7) | 0.0062 (7) | −0.0012 (7) |
C9A | 0.0578 (9) | 0.0512 (10) | 0.0613 (10) | −0.0055 (7) | 0.0072 (7) | −0.0112 (7) |
C10A | 0.0619 (9) | 0.0514 (10) | 0.0619 (10) | −0.0103 (7) | 0.0015 (7) | −0.0112 (7) |
C11A | 0.0634 (10) | 0.0682 (12) | 0.0699 (11) | −0.0054 (9) | −0.0009 (8) | −0.0085 (9) |
C12A | 0.0838 (12) | 0.0778 (14) | 0.0782 (13) | −0.0031 (10) | −0.0129 (11) | 0.0004 (10) |
C13A | 0.1153 (17) | 0.0920 (17) | 0.0673 (13) | 0.0020 (14) | 0.0173 (12) | −0.0061 (11) |
C14A | 0.0874 (12) | 0.0746 (13) | 0.0670 (11) | 0.0081 (10) | 0.0115 (10) | −0.0070 (9) |
C1B | 0.0621 (9) | 0.0429 (9) | 0.0784 (11) | −0.0073 (7) | 0.0079 (8) | 0.0064 (8) |
C2B | 0.0569 (9) | 0.0510 (11) | 0.1192 (16) | 0.0064 (8) | 0.0125 (10) | 0.0141 (10) |
C3B | 0.0976 (15) | 0.0580 (13) | 0.1147 (18) | −0.0033 (11) | 0.0511 (14) | −0.0099 (12) |
C4B | 0.1069 (16) | 0.0676 (13) | 0.0774 (13) | −0.0251 (12) | 0.0062 (12) | 0.0027 (10) |
C5B | 0.0660 (10) | 0.0661 (13) | 0.1003 (15) | −0.0070 (9) | −0.0056 (10) | 0.0189 (11) |
C6B | 0.0580 (9) | 0.0506 (10) | 0.0974 (14) | 0.0045 (8) | 0.0162 (9) | 0.0078 (9) |
C7B | 0.1016 (14) | 0.0753 (14) | 0.0894 (14) | −0.0289 (11) | −0.0016 (11) | 0.0128 (11) |
C8B | 0.0625 (9) | 0.0510 (10) | 0.0730 (11) | −0.0014 (8) | 0.0049 (8) | −0.0014 (8) |
C9B | 0.0568 (9) | 0.0542 (10) | 0.0710 (11) | −0.0029 (7) | −0.0004 (8) | −0.0137 (8) |
C10B | 0.0633 (9) | 0.0550 (10) | 0.0661 (10) | 0.0010 (8) | 0.0021 (8) | −0.0146 (8) |
C11B | 0.0618 (9) | 0.0694 (12) | 0.0688 (11) | 0.0019 (8) | 0.0036 (8) | −0.0104 (9) |
C12B | 0.0794 (12) | 0.0803 (14) | 0.0792 (13) | −0.0026 (10) | 0.0146 (10) | −0.0048 (10) |
C13B | 0.1127 (17) | 0.1077 (19) | 0.0719 (14) | −0.0131 (15) | −0.0150 (12) | −0.0173 (12) |
C14B | 0.0843 (12) | 0.0831 (15) | 0.0779 (13) | −0.0160 (11) | −0.0070 (10) | −0.0146 (11) |
S1A—C8A | 1.7259 (16) | C9A—C10A | 1.454 (2) |
S1A—C7A | 1.8187 (17) | C10A—C11A | 1.378 (2) |
S1B—C8B | 1.7272 (18) | C10A—C14A | 1.386 (2) |
S1B—C7B | 1.8207 (18) | C11A—C12A | 1.380 (3) |
O1A—C8A | 1.3603 (19) | C11A—H11A | 0.9300 |
O1A—C9A | 1.3688 (17) | C12A—H12A | 0.9300 |
O1B—C8B | 1.3557 (19) | C13A—C14A | 1.368 (3) |
O1B—C9B | 1.3655 (18) | C13A—H13A | 0.9300 |
N1A—C8A | 1.286 (2) | C14A—H14A | 0.9300 |
N1A—N2A | 1.4082 (19) | C1B—C6B | 1.370 (2) |
N2A—C9A | 1.284 (2) | C1B—C2B | 1.380 (2) |
N3A—C12A | 1.325 (2) | C1B—C7B | 1.495 (3) |
N3A—C13A | 1.328 (3) | C2B—C3B | 1.379 (3) |
N1B—C8B | 1.282 (2) | C2B—H2BA | 0.9300 |
N1B—N2B | 1.404 (2) | C3B—C4B | 1.378 (3) |
N2B—C9B | 1.284 (2) | C3B—H3BA | 0.9300 |
N3B—C12B | 1.326 (2) | C4B—C5B | 1.357 (3) |
N3B—C13B | 1.327 (3) | C4B—H4BA | 0.9300 |
C1A—C6A | 1.382 (2) | C5B—C6B | 1.359 (3) |
C1A—C2A | 1.386 (2) | C5B—H5BA | 0.9300 |
C1A—C7A | 1.500 (2) | C6B—H6BA | 0.9300 |
C2A—C3A | 1.375 (2) | C7B—H7BA | 0.9700 |
C2A—H2AA | 0.9300 | C7B—H7BB | 0.9700 |
C3A—C4A | 1.368 (2) | C9B—C10B | 1.452 (2) |
C3A—H3AA | 0.9300 | C10B—C11B | 1.378 (2) |
C4A—C5A | 1.367 (2) | C10B—C14B | 1.384 (2) |
C4A—H4AA | 0.9300 | C11B—C12B | 1.379 (2) |
C5A—C6A | 1.374 (2) | C11B—H11B | 0.9300 |
C5A—H5AA | 0.9300 | C12B—H12B | 0.9300 |
C6A—H6AA | 0.9300 | C13B—C14B | 1.370 (3) |
C7A—H7AA | 0.9700 | C13B—H13B | 0.9300 |
C7A—H7AB | 0.9700 | C14B—H14B | 0.9300 |
C8A—S1A—C7A | 97.83 (8) | N3A—C13A—H13A | 117.6 |
C8B—S1B—C7B | 96.83 (9) | C14A—C13A—H13A | 117.6 |
C8A—O1A—C9A | 102.13 (12) | C13A—C14A—C10A | 118.61 (19) |
C8B—O1B—C9B | 102.13 (12) | C13A—C14A—H14A | 120.7 |
C8A—N1A—N2A | 105.52 (14) | C10A—C14A—H14A | 120.7 |
C9A—N2A—N1A | 106.76 (13) | C6B—C1B—C2B | 118.54 (17) |
C12A—N3A—C13A | 115.50 (18) | C6B—C1B—C7B | 121.60 (17) |
C8B—N1B—N2B | 105.35 (14) | C2B—C1B—C7B | 119.82 (17) |
C9B—N2B—N1B | 106.89 (14) | C3B—C2B—C1B | 120.29 (17) |
C12B—N3B—C13B | 116.45 (18) | C3B—C2B—H2BA | 119.9 |
C6A—C1A—C2A | 118.39 (15) | C1B—C2B—H2BA | 119.9 |
C6A—C1A—C7A | 120.58 (16) | C4B—C3B—C2B | 119.58 (18) |
C2A—C1A—C7A | 121.01 (15) | C4B—C3B—H3BA | 120.2 |
C3A—C2A—C1A | 120.69 (15) | C2B—C3B—H3BA | 120.2 |
C3A—C2A—H2AA | 119.7 | C5B—C4B—C3B | 120.0 (2) |
C1A—C2A—H2AA | 119.7 | C5B—C4B—H4BA | 120.0 |
C4A—C3A—C2A | 120.24 (17) | C3B—C4B—H4BA | 120.0 |
C4A—C3A—H3AA | 119.9 | C4B—C5B—C6B | 120.30 (19) |
C2A—C3A—H3AA | 119.9 | C4B—C5B—H5BA | 119.8 |
C5A—C4A—C3A | 119.59 (17) | C6B—C5B—H5BA | 119.8 |
C5A—C4A—H4AA | 120.2 | C5B—C6B—C1B | 121.32 (17) |
C3A—C4A—H4AA | 120.2 | C5B—C6B—H6BA | 119.3 |
C4A—C5A—C6A | 120.71 (16) | C1B—C6B—H6BA | 119.3 |
C4A—C5A—H5AA | 119.6 | C1B—C7B—S1B | 110.03 (13) |
C6A—C5A—H5AA | 119.6 | C1B—C7B—H7BA | 109.7 |
C5A—C6A—C1A | 120.38 (16) | S1B—C7B—H7BA | 109.7 |
C5A—C6A—H6AA | 119.8 | C1B—C7B—H7BB | 109.7 |
C1A—C6A—H6AA | 119.8 | S1B—C7B—H7BB | 109.7 |
C1A—C7A—S1A | 109.48 (11) | H7BA—C7B—H7BB | 108.2 |
C1A—C7A—H7AA | 109.8 | N1B—C8B—O1B | 113.54 (15) |
S1A—C7A—H7AA | 109.8 | N1B—C8B—S1B | 128.18 (14) |
C1A—C7A—H7AB | 109.8 | O1B—C8B—S1B | 118.28 (12) |
S1A—C7A—H7AB | 109.8 | N2B—C9B—O1B | 112.08 (15) |
H7AA—C7A—H7AB | 108.2 | N2B—C9B—C10B | 127.89 (16) |
N1A—C8A—O1A | 113.30 (14) | O1B—C9B—C10B | 120.02 (14) |
N1A—C8A—S1A | 128.77 (14) | C11B—C10B—C14B | 118.01 (17) |
O1A—C8A—S1A | 117.93 (11) | C11B—C10B—C9B | 122.71 (15) |
N2A—C9A—O1A | 112.28 (14) | C14B—C10B—C9B | 119.27 (16) |
N2A—C9A—C10A | 128.20 (15) | C10B—C11B—C12B | 118.59 (17) |
O1A—C9A—C10A | 119.51 (14) | C10B—C11B—H11B | 120.7 |
C11A—C10A—C14A | 117.94 (16) | C12B—C11B—H11B | 120.7 |
C11A—C10A—C9A | 122.69 (15) | N3B—C12B—C11B | 124.05 (19) |
C14A—C10A—C9A | 119.37 (16) | N3B—C12B—H12B | 118.0 |
C10A—C11A—C12A | 118.23 (17) | C11B—C12B—H12B | 118.0 |
C10A—C11A—H11A | 120.9 | N3B—C13B—C14B | 124.2 (2) |
C12A—C11A—H11A | 120.9 | N3B—C13B—H13B | 117.9 |
N3A—C12A—C11A | 124.87 (19) | C14B—C13B—H13B | 117.9 |
N3A—C12A—H12A | 117.6 | C13B—C14B—C10B | 118.68 (19) |
C11A—C12A—H12A | 117.6 | C13B—C14B—H14B | 120.7 |
N3A—C13A—C14A | 124.8 (2) | C10B—C14B—H14B | 120.7 |
C8A—N1A—N2A—C9A | 0.01 (18) | C9A—C10A—C14A—C13A | −178.79 (17) |
C8B—N1B—N2B—C9B | −0.2 (2) | C6B—C1B—C2B—C3B | −0.3 (3) |
C6A—C1A—C2A—C3A | −0.4 (2) | C7B—C1B—C2B—C3B | −177.88 (16) |
C7A—C1A—C2A—C3A | −178.75 (15) | C1B—C2B—C3B—C4B | 0.4 (3) |
C1A—C2A—C3A—C4A | 0.1 (3) | C2B—C3B—C4B—C5B | 0.1 (3) |
C2A—C3A—C4A—C5A | 0.2 (3) | C3B—C4B—C5B—C6B | −0.6 (3) |
C3A—C4A—C5A—C6A | −0.1 (3) | C4B—C5B—C6B—C1B | 0.6 (3) |
C4A—C5A—C6A—C1A | −0.2 (3) | C2B—C1B—C6B—C5B | −0.2 (2) |
C2A—C1A—C6A—C5A | 0.4 (2) | C7B—C1B—C6B—C5B | 177.33 (16) |
C7A—C1A—C6A—C5A | 178.84 (15) | C6B—C1B—C7B—S1B | 76.6 (2) |
C6A—C1A—C7A—S1A | 74.14 (18) | C2B—C1B—C7B—S1B | −105.87 (17) |
C2A—C1A—C7A—S1A | −107.52 (16) | C8B—S1B—C7B—C1B | 173.59 (15) |
C8A—S1A—C7A—C1A | −178.31 (13) | N2B—N1B—C8B—O1B | 0.8 (2) |
N2A—N1A—C8A—O1A | 0.50 (19) | N2B—N1B—C8B—S1B | −178.30 (13) |
N2A—N1A—C8A—S1A | −178.98 (12) | C9B—O1B—C8B—N1B | −0.99 (18) |
C9A—O1A—C8A—N1A | −0.77 (17) | C9B—O1B—C8B—S1B | 178.19 (11) |
C9A—O1A—C8A—S1A | 178.77 (11) | C7B—S1B—C8B—N1B | −5.83 (19) |
C7A—S1A—C8A—N1A | −4.65 (18) | C7B—S1B—C8B—O1B | 175.13 (14) |
C7A—S1A—C8A—O1A | 175.89 (13) | N1B—N2B—C9B—O1B | −0.4 (2) |
N1A—N2A—C9A—O1A | −0.50 (18) | N1B—N2B—C9B—C10B | 178.67 (16) |
N1A—N2A—C9A—C10A | 178.56 (15) | C8B—O1B—C9B—N2B | 0.82 (18) |
C8A—O1A—C9A—N2A | 0.77 (17) | C8B—O1B—C9B—C10B | −178.34 (14) |
C8A—O1A—C9A—C10A | −178.39 (13) | N2B—C9B—C10B—C11B | 174.47 (18) |
N2A—C9A—C10A—C11A | 175.35 (17) | O1B—C9B—C10B—C11B | −6.5 (2) |
O1A—C9A—C10A—C11A | −5.6 (2) | N2B—C9B—C10B—C14B | −6.2 (3) |
N2A—C9A—C10A—C14A | −5.8 (3) | O1B—C9B—C10B—C14B | 172.81 (15) |
O1A—C9A—C10A—C14A | 173.19 (15) | C14B—C10B—C11B—C12B | −1.1 (3) |
C14A—C10A—C11A—C12A | −0.9 (2) | C9B—C10B—C11B—C12B | 178.21 (16) |
C9A—C10A—C11A—C12A | 177.92 (16) | C13B—N3B—C12B—C11B | −0.3 (3) |
C13A—N3A—C12A—C11A | −0.1 (3) | C10B—C11B—C12B—N3B | 0.9 (3) |
C10A—C11A—C12A—N3A | 1.0 (3) | C12B—N3B—C13B—C14B | 0.0 (3) |
C12A—N3A—C13A—C14A | −0.8 (3) | N3B—C13B—C14B—C10B | −0.3 (4) |
N3A—C13A—C14A—C10A | 0.8 (3) | C11B—C10B—C14B—C13B | 0.9 (3) |
C11A—C10A—C14A—C13A | 0.1 (3) | C9B—C10B—C14B—C13B | −178.49 (19) |