Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032381/ac6207sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032381/ac6207Isup2.hkl |
CCDC reference: 283574
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
C27H21Cl2N3O2S·CH2Cl2 | F(000) = 2496 |
Mr = 607.35 | Dx = 1.427 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 3753 reflections |
a = 18.564 (3) Å | θ = 2.3–19.8° |
b = 10.6834 (17) Å | µ = 0.52 mm−1 |
c = 28.510 (4) Å | T = 293 K |
V = 5654.3 (15) Å3 | Plate, colourless |
Z = 8 | 0.30 × 0.20 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 3655 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.050 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
φ and ω scans | h = −17→22 |
26881 measured reflections | k = −12→12 |
4964 independent reflections | l = −33→33 |
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)] = 0.087 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.211 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0768P)2 + 7.6281P] where P = (Fo2 + 2Fc2)/3 |
4964 reflections | (Δ/σ)max < 0.001 |
346 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
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 | ||
C1 | 0.2659 (3) | 0.2158 (6) | 0.33974 (19) | 0.0824 (16) | |
H1A | 0.2606 | 0.1258 | 0.3425 | 0.099* | |
H1B | 0.2236 | 0.2546 | 0.3534 | 0.099* | |
C2 | 0.3319 (3) | 0.2571 (6) | 0.3663 (2) | 0.0827 (16) | |
H2A | 0.3216 | 0.2571 | 0.3996 | 0.099* | |
H2B | 0.3707 | 0.1981 | 0.3607 | 0.099* | |
C3 | 0.3554 (3) | 0.3844 (5) | 0.35173 (17) | 0.0730 (14) | |
H3A | 0.3968 | 0.4085 | 0.3704 | 0.088* | |
H3B | 0.3170 | 0.4432 | 0.3584 | 0.088* | |
C4 | 0.3751 (2) | 0.3943 (4) | 0.30034 (15) | 0.0523 (10) | |
H4A | 0.3780 | 0.4819 | 0.2915 | 0.063* | |
H4B | 0.4221 | 0.3570 | 0.2953 | 0.063* | |
C5 | 0.3202 (2) | 0.3292 (4) | 0.26984 (16) | 0.0486 (10) | |
C6 | 0.2709 (2) | 0.2510 (4) | 0.28884 (17) | 0.0622 (12) | |
C7 | 0.2535 (2) | 0.2724 (4) | 0.20251 (17) | 0.0585 (12) | |
C8 | 0.3112 (2) | 0.3417 (4) | 0.22002 (15) | 0.0465 (10) | |
C9 | 0.3501 (2) | 0.4106 (4) | 0.18605 (14) | 0.0450 (10) | |
C10 | 0.3271 (2) | 0.4080 (4) | 0.13950 (15) | 0.0499 (10) | |
C11 | 0.2667 (2) | 0.3322 (5) | 0.12678 (17) | 0.0611 (12) | |
C12 | 0.2410 (3) | 0.3199 (6) | 0.07692 (18) | 0.0927 (19) | |
H12A | 0.2030 | 0.2591 | 0.0755 | 0.139* | |
H12B | 0.2803 | 0.2934 | 0.0574 | 0.139* | |
H12C | 0.2234 | 0.3993 | 0.0661 | 0.139* | |
C13 | 0.3653 (2) | 0.4838 (4) | 0.10534 (15) | 0.0531 (11) | |
C14 | 0.4436 (2) | 0.5392 (4) | 0.16988 (14) | 0.0477 (10) | |
C15 | 0.4667 (2) | 0.6279 (4) | 0.09199 (14) | 0.0488 (10) | |
C16 | 0.4567 (2) | 0.7552 (5) | 0.09290 (16) | 0.0614 (12) | |
H16 | 0.4242 | 0.7902 | 0.1139 | 0.074* | |
C17 | 0.4948 (3) | 0.8313 (5) | 0.06277 (18) | 0.0723 (14) | |
H17 | 0.4889 | 0.9177 | 0.0634 | 0.087* | |
C18 | 0.5417 (3) | 0.7757 (6) | 0.03177 (17) | 0.0744 (15) | |
C19 | 0.5518 (3) | 0.6506 (6) | 0.03017 (17) | 0.0753 (15) | |
H19 | 0.5840 | 0.6158 | 0.0089 | 0.090* | |
C20 | 0.5133 (3) | 0.5748 (5) | 0.06072 (16) | 0.0654 (13) | |
H20 | 0.5193 | 0.4884 | 0.0599 | 0.078* | |
C21 | 0.5288 (2) | 0.5946 (4) | 0.22710 (15) | 0.0529 (11) | |
C22 | 0.5892 (3) | 0.5244 (5) | 0.23505 (18) | 0.0653 (13) | |
H22 | 0.6115 | 0.4814 | 0.2107 | 0.078* | |
C23 | 0.6166 (3) | 0.5187 (5) | 0.2803 (2) | 0.0724 (14) | |
H23 | 0.6580 | 0.4728 | 0.2867 | 0.087* | |
C24 | 0.5817 (3) | 0.5816 (5) | 0.31515 (17) | 0.0658 (14) | |
C25 | 0.5206 (3) | 0.6535 (4) | 0.30807 (16) | 0.0599 (12) | |
C26 | 0.4955 (2) | 0.6593 (4) | 0.26207 (16) | 0.0566 (11) | |
H26 | 0.4554 | 0.7081 | 0.2551 | 0.068* | |
C27 | 0.3126 (8) | 0.8419 (11) | 0.4723 (3) | 0.200 (6) | |
H27A | 0.2651 | 0.8128 | 0.4814 | 0.240* | |
H27B | 0.3353 | 0.8764 | 0.5001 | 0.240* | |
C28 | 0.4822 (4) | 0.7210 (6) | 0.3466 (2) | 0.098 (2) | |
H28A | 0.4630 | 0.6613 | 0.3684 | 0.147* | |
H28B | 0.4436 | 0.7697 | 0.3335 | 0.147* | |
H28C | 0.5154 | 0.7753 | 0.3625 | 0.147* | |
Cl1 | 0.59173 (11) | 0.8722 (2) | −0.00558 (7) | 0.1375 (9) | |
Cl2 | 0.61764 (11) | 0.57036 (17) | 0.37195 (5) | 0.1085 (7) | |
Cl3 | 0.3607 (3) | 0.7189 (6) | 0.45444 (16) | 0.311 (3) | |
Cl4 | 0.3031 (3) | 0.9541 (4) | 0.43380 (15) | 0.291 (3) | |
N1 | 0.23064 (19) | 0.2654 (4) | 0.15806 (15) | 0.0662 (11) | |
N2 | 0.40997 (17) | 0.4764 (3) | 0.20098 (11) | 0.0462 (8) | |
N3 | 0.42573 (17) | 0.5493 (3) | 0.12341 (11) | 0.0480 (8) | |
O1 | 0.35156 (17) | 0.4962 (4) | 0.06393 (11) | 0.0732 (10) | |
O2 | 0.50390 (16) | 0.6030 (3) | 0.18021 (10) | 0.0615 (8) | |
S1 | 0.21159 (7) | 0.18893 (13) | 0.24750 (5) | 0.0736 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.078 (4) | 0.080 (4) | 0.089 (4) | −0.012 (3) | 0.016 (3) | 0.021 (3) |
C2 | 0.089 (4) | 0.084 (4) | 0.075 (3) | −0.004 (3) | 0.008 (3) | 0.022 (3) |
C3 | 0.079 (3) | 0.079 (4) | 0.061 (3) | −0.005 (3) | −0.001 (3) | 0.008 (3) |
C4 | 0.049 (2) | 0.045 (2) | 0.063 (3) | −0.0005 (19) | 0.000 (2) | 0.003 (2) |
C5 | 0.041 (2) | 0.037 (2) | 0.068 (3) | 0.0028 (18) | 0.005 (2) | 0.0024 (19) |
C6 | 0.052 (3) | 0.055 (3) | 0.079 (3) | −0.001 (2) | 0.010 (2) | 0.007 (2) |
C7 | 0.046 (2) | 0.050 (3) | 0.079 (3) | −0.004 (2) | 0.005 (2) | −0.015 (2) |
C8 | 0.036 (2) | 0.039 (2) | 0.064 (3) | 0.0014 (17) | 0.0055 (19) | −0.007 (2) |
C9 | 0.038 (2) | 0.040 (2) | 0.056 (2) | 0.0042 (18) | 0.0010 (18) | −0.0096 (19) |
C10 | 0.038 (2) | 0.054 (3) | 0.058 (3) | 0.0000 (19) | 0.0011 (19) | −0.012 (2) |
C11 | 0.048 (3) | 0.069 (3) | 0.067 (3) | −0.003 (2) | 0.000 (2) | −0.022 (2) |
C12 | 0.073 (3) | 0.133 (5) | 0.072 (3) | −0.042 (4) | −0.005 (3) | −0.029 (3) |
C13 | 0.045 (2) | 0.066 (3) | 0.048 (3) | 0.005 (2) | −0.0056 (19) | −0.013 (2) |
C14 | 0.043 (2) | 0.049 (2) | 0.050 (2) | −0.0061 (19) | 0.0003 (19) | −0.003 (2) |
C15 | 0.047 (2) | 0.056 (3) | 0.044 (2) | 0.000 (2) | −0.0010 (19) | 0.0010 (19) |
C16 | 0.059 (3) | 0.069 (3) | 0.056 (3) | 0.010 (2) | 0.006 (2) | 0.005 (2) |
C17 | 0.075 (3) | 0.067 (3) | 0.075 (3) | 0.005 (3) | 0.003 (3) | 0.018 (3) |
C18 | 0.064 (3) | 0.098 (4) | 0.061 (3) | 0.000 (3) | 0.006 (3) | 0.029 (3) |
C19 | 0.070 (3) | 0.101 (4) | 0.055 (3) | 0.010 (3) | 0.020 (3) | 0.002 (3) |
C20 | 0.064 (3) | 0.070 (3) | 0.062 (3) | 0.000 (3) | 0.011 (2) | −0.010 (2) |
C21 | 0.045 (2) | 0.058 (3) | 0.056 (3) | −0.018 (2) | −0.006 (2) | 0.009 (2) |
C22 | 0.065 (3) | 0.056 (3) | 0.074 (3) | −0.005 (2) | 0.001 (3) | −0.003 (2) |
C23 | 0.071 (3) | 0.059 (3) | 0.087 (4) | −0.004 (3) | −0.016 (3) | 0.011 (3) |
C24 | 0.079 (4) | 0.057 (3) | 0.061 (3) | −0.028 (3) | −0.018 (3) | 0.013 (2) |
C25 | 0.066 (3) | 0.055 (3) | 0.058 (3) | −0.024 (2) | 0.001 (2) | 0.002 (2) |
C26 | 0.042 (2) | 0.058 (3) | 0.069 (3) | −0.011 (2) | −0.001 (2) | 0.004 (2) |
C27 | 0.338 (16) | 0.175 (10) | 0.087 (6) | −0.118 (11) | 0.021 (8) | −0.002 (6) |
C28 | 0.110 (5) | 0.103 (5) | 0.080 (4) | −0.022 (4) | 0.018 (3) | −0.016 (3) |
Cl1 | 0.1290 (16) | 0.1603 (19) | 0.1234 (15) | 0.0024 (14) | 0.0457 (12) | 0.0790 (14) |
Cl2 | 0.1475 (15) | 0.1014 (12) | 0.0767 (10) | −0.0401 (11) | −0.0489 (10) | 0.0260 (9) |
Cl3 | 0.361 (6) | 0.386 (7) | 0.187 (4) | 0.145 (6) | −0.036 (4) | −0.053 (4) |
Cl4 | 0.357 (6) | 0.259 (4) | 0.257 (4) | −0.162 (4) | −0.178 (4) | 0.092 (4) |
N1 | 0.048 (2) | 0.073 (3) | 0.078 (3) | −0.015 (2) | 0.002 (2) | −0.021 (2) |
N2 | 0.0419 (18) | 0.049 (2) | 0.0473 (19) | −0.0067 (16) | −0.0030 (15) | −0.0008 (16) |
N3 | 0.0460 (19) | 0.057 (2) | 0.0415 (18) | −0.0051 (16) | −0.0015 (15) | −0.0015 (16) |
O1 | 0.068 (2) | 0.101 (3) | 0.051 (2) | −0.015 (2) | −0.0089 (16) | −0.0067 (18) |
O2 | 0.0536 (18) | 0.080 (2) | 0.0514 (17) | −0.0270 (16) | −0.0042 (14) | 0.0091 (15) |
S1 | 0.0533 (7) | 0.0681 (8) | 0.0995 (10) | −0.0219 (6) | 0.0085 (7) | 0.0010 (7) |
C1—C6 | 1.502 (7) | C14—N3 | 1.370 (5) |
C1—C2 | 1.506 (8) | C15—C20 | 1.366 (6) |
C1—H1A | 0.9700 | C15—C16 | 1.373 (6) |
C1—H1B | 0.9700 | C15—N3 | 1.444 (5) |
C2—C3 | 1.488 (7) | C16—C17 | 1.377 (7) |
C2—H2A | 0.9700 | C16—H16 | 0.9300 |
C2—H2B | 0.9700 | C17—C18 | 1.376 (7) |
C3—C4 | 1.514 (6) | C17—H17 | 0.9300 |
C3—H3A | 0.9700 | C18—C19 | 1.350 (8) |
C3—H3B | 0.9700 | C18—Cl1 | 1.749 (5) |
C4—C5 | 1.510 (6) | C19—C20 | 1.387 (7) |
C4—H4A | 0.9700 | C19—H19 | 0.9300 |
C4—H4B | 0.9700 | C20—H20 | 0.9300 |
C5—C6 | 1.352 (6) | C21—C26 | 1.362 (6) |
C5—C8 | 1.436 (6) | C21—C22 | 1.368 (6) |
C6—S1 | 1.744 (5) | C21—O2 | 1.418 (5) |
C7—N1 | 1.338 (6) | C22—C23 | 1.387 (7) |
C7—C8 | 1.396 (6) | C22—H22 | 0.9300 |
C7—S1 | 1.745 (5) | C23—C24 | 1.363 (8) |
C8—C9 | 1.414 (6) | C23—H23 | 0.9300 |
C9—N2 | 1.382 (5) | C24—C25 | 1.386 (7) |
C9—C10 | 1.394 (6) | C24—Cl2 | 1.755 (5) |
C10—C11 | 1.429 (6) | C25—C26 | 1.393 (6) |
C10—C13 | 1.452 (6) | C25—C28 | 1.494 (7) |
C11—N1 | 1.324 (6) | C26—H26 | 0.9300 |
C11—C12 | 1.505 (7) | C27—Cl4 | 1.635 (11) |
C12—H12A | 0.9600 | C27—Cl3 | 1.668 (14) |
C12—H12B | 0.9600 | C27—H27A | 0.9700 |
C12—H12C | 0.9600 | C27—H27B | 0.9700 |
C13—O1 | 1.215 (5) | C28—H28A | 0.9600 |
C13—N3 | 1.419 (5) | C28—H28B | 0.9600 |
C14—N2 | 1.275 (5) | C28—H28C | 0.9600 |
C14—O2 | 1.343 (5) | ||
C6—C1—C2 | 111.2 (4) | O2—C14—N3 | 112.0 (3) |
C6—C1—H1A | 109.4 | C20—C15—C16 | 120.6 (4) |
C2—C1—H1A | 109.4 | C20—C15—N3 | 119.8 (4) |
C6—C1—H1B | 109.4 | C16—C15—N3 | 119.6 (4) |
C2—C1—H1B | 109.4 | C15—C16—C17 | 120.3 (5) |
H1A—C1—H1B | 108.0 | C15—C16—H16 | 119.9 |
C3—C2—C1 | 111.5 (5) | C17—C16—H16 | 119.9 |
C3—C2—H2A | 109.3 | C18—C17—C16 | 118.1 (5) |
C1—C2—H2A | 109.3 | C18—C17—H17 | 120.9 |
C3—C2—H2B | 109.3 | C16—C17—H17 | 120.9 |
C1—C2—H2B | 109.3 | C19—C18—C17 | 122.4 (5) |
H2A—C2—H2B | 108.0 | C19—C18—Cl1 | 119.3 (4) |
C2—C3—C4 | 113.9 (4) | C17—C18—Cl1 | 118.2 (5) |
C2—C3—H3A | 108.8 | C18—C19—C20 | 119.1 (5) |
C4—C3—H3A | 108.8 | C18—C19—H19 | 120.5 |
C2—C3—H3B | 108.8 | C20—C19—H19 | 120.5 |
C4—C3—H3B | 108.8 | C15—C20—C19 | 119.6 (5) |
H3A—C3—H3B | 107.7 | C15—C20—H20 | 120.2 |
C5—C4—C3 | 111.2 (4) | C19—C20—H20 | 120.2 |
C5—C4—H4A | 109.4 | C26—C21—C22 | 122.0 (4) |
C3—C4—H4A | 109.4 | C26—C21—O2 | 120.6 (4) |
C5—C4—H4B | 109.4 | C22—C21—O2 | 117.3 (4) |
C3—C4—H4B | 109.4 | C21—C22—C23 | 118.5 (5) |
H4A—C4—H4B | 108.0 | C21—C22—H22 | 120.7 |
C6—C5—C8 | 112.1 (4) | C23—C22—H22 | 120.7 |
C6—C5—C4 | 120.7 (4) | C24—C23—C22 | 118.9 (5) |
C8—C5—C4 | 127.2 (4) | C24—C23—H23 | 120.5 |
C5—C6—C1 | 125.7 (5) | C22—C23—H23 | 120.5 |
C5—C6—S1 | 113.0 (4) | C23—C24—C25 | 123.7 (5) |
C1—C6—S1 | 121.2 (4) | C23—C24—Cl2 | 117.4 (4) |
N1—C7—C8 | 127.7 (4) | C25—C24—Cl2 | 118.9 (4) |
N1—C7—S1 | 121.8 (3) | C24—C25—C26 | 115.9 (4) |
C8—C7—S1 | 110.5 (4) | C24—C25—C28 | 123.5 (5) |
C7—C8—C9 | 115.0 (4) | C26—C25—C28 | 120.7 (5) |
C7—C8—C5 | 113.1 (4) | C21—C26—C25 | 120.9 (4) |
C9—C8—C5 | 131.8 (4) | C21—C26—H26 | 119.5 |
N2—C9—C10 | 123.3 (4) | C25—C26—H26 | 119.5 |
N2—C9—C8 | 117.6 (4) | Cl4—C27—Cl3 | 115.4 (7) |
C10—C9—C8 | 119.0 (4) | Cl4—C27—H27A | 108.4 |
C9—C10—C11 | 119.5 (4) | Cl3—C27—H27A | 108.4 |
C9—C10—C13 | 118.5 (4) | Cl4—C27—H27B | 108.4 |
C11—C10—C13 | 121.9 (4) | Cl3—C27—H27B | 108.4 |
N1—C11—C10 | 122.1 (4) | H27A—C27—H27B | 107.5 |
N1—C11—C12 | 115.4 (4) | C25—C28—H28A | 109.5 |
C10—C11—C12 | 122.5 (5) | C25—C28—H28B | 109.5 |
C11—C12—H12A | 109.5 | H28A—C28—H28B | 109.5 |
C11—C12—H12B | 109.5 | C25—C28—H28C | 109.5 |
H12A—C12—H12B | 109.5 | H28A—C28—H28C | 109.5 |
C11—C12—H12C | 109.5 | H28B—C28—H28C | 109.5 |
H12A—C12—H12C | 109.5 | C11—N1—C7 | 116.6 (4) |
H12B—C12—H12C | 109.5 | C14—N2—C9 | 116.6 (3) |
O1—C13—N3 | 117.7 (4) | C14—N3—C13 | 120.2 (3) |
O1—C13—C10 | 127.6 (4) | C14—N3—C15 | 121.2 (3) |
N3—C13—C10 | 114.7 (4) | C13—N3—C15 | 118.5 (3) |
N2—C14—O2 | 121.5 (4) | C14—O2—C21 | 116.5 (3) |
N2—C14—N3 | 126.5 (4) | C6—S1—C7 | 91.2 (2) |
C6—C1—C2—C3 | 41.6 (7) | N3—C15—C20—C19 | 179.1 (4) |
C1—C2—C3—C4 | −60.6 (6) | C18—C19—C20—C15 | −0.6 (8) |
C2—C3—C4—C5 | 44.7 (6) | C26—C21—C22—C23 | 0.6 (7) |
C3—C4—C5—C6 | −13.5 (6) | O2—C21—C22—C23 | 177.4 (4) |
C3—C4—C5—C8 | 164.9 (4) | C21—C22—C23—C24 | 1.0 (7) |
C8—C5—C6—C1 | 179.0 (5) | C22—C23—C24—C25 | −1.1 (7) |
C4—C5—C6—C1 | −2.4 (7) | C22—C23—C24—Cl2 | 179.3 (4) |
C8—C5—C6—S1 | 0.0 (5) | C23—C24—C25—C26 | −0.2 (7) |
C4—C5—C6—S1 | 178.6 (3) | Cl2—C24—C25—C26 | 179.3 (3) |
C2—C1—C6—C5 | −11.8 (8) | C23—C24—C25—C28 | 179.3 (5) |
C2—C1—C6—S1 | 167.1 (4) | Cl2—C24—C25—C28 | −1.1 (6) |
N1—C7—C8—C9 | −0.9 (7) | C22—C21—C26—C25 | −2.0 (7) |
S1—C7—C8—C9 | 178.5 (3) | O2—C21—C26—C25 | −178.7 (4) |
N1—C7—C8—C5 | 179.2 (4) | C24—C25—C26—C21 | 1.8 (6) |
S1—C7—C8—C5 | −1.4 (5) | C28—C25—C26—C21 | −177.8 (4) |
C6—C5—C8—C7 | 0.9 (5) | C10—C11—N1—C7 | 0.1 (7) |
C4—C5—C8—C7 | −177.6 (4) | C12—C11—N1—C7 | 178.5 (5) |
C6—C5—C8—C9 | −179.0 (4) | C8—C7—N1—C11 | −0.2 (7) |
C4—C5—C8—C9 | 2.5 (7) | S1—C7—N1—C11 | −179.6 (4) |
C7—C8—C9—N2 | −177.0 (4) | O2—C14—N2—C9 | −177.7 (4) |
C5—C8—C9—N2 | 2.9 (6) | N3—C14—N2—C9 | 1.0 (6) |
C7—C8—C9—C10 | 2.2 (5) | C10—C9—N2—C14 | 1.7 (6) |
C5—C8—C9—C10 | −177.9 (4) | C8—C9—N2—C14 | −179.1 (4) |
N2—C9—C10—C11 | 176.8 (4) | N2—C14—N3—C13 | −1.5 (7) |
C8—C9—C10—C11 | −2.4 (6) | O2—C14—N3—C13 | 177.3 (4) |
N2—C9—C10—C13 | −3.7 (6) | N2—C14—N3—C15 | 177.4 (4) |
C8—C9—C10—C13 | 177.1 (4) | O2—C14—N3—C15 | −3.8 (5) |
C9—C10—C11—N1 | 1.2 (7) | O1—C13—N3—C14 | 179.7 (4) |
C13—C10—C11—N1 | −178.2 (4) | C10—C13—N3—C14 | −0.6 (6) |
C9—C10—C11—C12 | −177.0 (5) | O1—C13—N3—C15 | 0.9 (6) |
C13—C10—C11—C12 | 3.5 (7) | C10—C13—N3—C15 | −179.5 (4) |
C9—C10—C13—O1 | −177.4 (4) | C20—C15—N3—C14 | 104.6 (5) |
C11—C10—C13—O1 | 2.1 (7) | C16—C15—N3—C14 | −77.3 (5) |
C9—C10—C13—N3 | 3.0 (6) | C20—C15—N3—C13 | −76.5 (5) |
C11—C10—C13—N3 | −177.5 (4) | C16—C15—N3—C13 | 101.6 (5) |
C20—C15—C16—C17 | −1.1 (7) | N2—C14—O2—C21 | 1.3 (6) |
N3—C15—C16—C17 | −179.2 (4) | N3—C14—O2—C21 | −177.5 (4) |
C15—C16—C17—C18 | 0.8 (7) | C26—C21—O2—C14 | −75.8 (5) |
C16—C17—C18—C19 | −0.3 (8) | C22—C21—O2—C14 | 107.3 (4) |
C16—C17—C18—Cl1 | −178.5 (4) | C5—C6—S1—C7 | −0.7 (4) |
C17—C18—C19—C20 | 0.2 (8) | C1—C6—S1—C7 | −179.7 (4) |
Cl1—C18—C19—C20 | 178.3 (4) | N1—C7—S1—C6 | −179.3 (4) |
C16—C15—C20—C19 | 1.0 (7) | C8—C7—S1—C6 | 1.2 (3) |