Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009742/wn6242sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009742/wn6242Isup2.hkl |
CCDC reference: 239290
Data collection: SMART (Bruker, 19978); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C15H11ClN2S | F(000) = 1184 |
Mr = 286.77 | Dx = 1.388 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.968 (5) Å | Cell parameters from 998 reflections |
b = 14.602 (5) Å | θ = 3.0–22.1° |
c = 15.271 (4) Å | µ = 0.42 mm−1 |
β = 118.24 (2)° | T = 293 K |
V = 2744.0 (15) Å3 | Block, colorless |
Z = 8 | 0.40 × 0.25 × 0.25 mm |
Bruker SMART CCD area-detector diffractometer | 4801 independent reflections |
Radiation source: fine-focus sealed tube | 2142 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→16 |
Tmin = 0.767, Tmax = 0.901 | k = −17→16 |
9474 measured reflections | l = −18→6 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3 |
4801 reflections | (Δ/σ)max < 0.001 |
346 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Experimental. IR spectra were obtained on a Shimadzu-IR 435 spectrometer. 1H NMR spectra were recorded on a Bruker AC—P200 spectrometer with TMS as the internal standard. Elemental analysis was performed on a Yanaco MT-3 instrument. Melting points were determined with a Yanaco MP-500 apparatus and uncorrected. |
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 | ||
Cl1 | 0.34759 (9) | 0.67047 (8) | 0.10227 (9) | 0.0778 (4) | |
Cl2 | 0.84191 (9) | −0.09952 (8) | 0.08796 (10) | 0.0840 (4) | |
S1 | 0.18121 (8) | 0.54810 (8) | 0.11716 (8) | 0.0548 (3) | |
S2 | 0.66900 (9) | 0.01735 (7) | 0.10105 (8) | 0.0544 (3) | |
N1 | 0.0695 (3) | 0.6476 (3) | 0.1702 (3) | 0.0736 (12) | |
N2 | 0.0306 (3) | 0.5597 (3) | 0.1639 (3) | 0.0713 (11) | |
N3 | 0.5294 (3) | 0.0013 (2) | 0.1626 (3) | 0.0607 (10) | |
N4 | 0.5708 (3) | −0.0848 (2) | 0.1666 (3) | 0.0657 (11) | |
C1 | 0.1115 (3) | 0.3404 (3) | 0.1017 (3) | 0.0665 (13) | |
H1 | 0.1684 | 0.3602 | 0.0910 | 0.080* | |
C2 | 0.0847 (4) | 0.2475 (3) | 0.0926 (3) | 0.0740 (14) | |
H2 | 0.1243 | 0.2064 | 0.0759 | 0.089* | |
C3 | 0.0011 (4) | 0.2152 (3) | 0.1078 (3) | 0.0692 (14) | |
C4 | −0.0556 (4) | 0.2788 (3) | 0.1309 (3) | 0.0700 (14) | |
H4 | −0.1132 | 0.2591 | 0.1406 | 0.084* | |
C5 | −0.0307 (3) | 0.3703 (3) | 0.1405 (3) | 0.0645 (13) | |
H5 | −0.0712 | 0.4109 | 0.1567 | 0.077* | |
C6 | 0.0544 (3) | 0.4028 (3) | 0.1263 (3) | 0.0458 (11) | |
C7 | 0.0806 (3) | 0.5012 (3) | 0.1373 (3) | 0.0442 (10) | |
C8 | 0.1481 (3) | 0.6533 (3) | 0.1471 (3) | 0.0448 (10) | |
C9 | 0.1968 (3) | 0.7432 (3) | 0.1492 (3) | 0.0481 (11) | |
C10 | 0.1515 (3) | 0.8198 (3) | 0.1713 (3) | 0.0656 (13) | |
H10 | 0.0924 | 0.8119 | 0.1828 | 0.079* | |
C11 | 0.1927 (4) | 0.9063 (3) | 0.1762 (4) | 0.0823 (15) | |
H11 | 0.1619 | 0.9559 | 0.1919 | 0.099* | |
C12 | 0.2786 (4) | 0.9199 (4) | 0.1582 (4) | 0.0829 (16) | |
H12 | 0.3060 | 0.9786 | 0.1617 | 0.099* | |
C13 | 0.3246 (4) | 0.8469 (4) | 0.1350 (3) | 0.0712 (14) | |
H13 | 0.3828 | 0.8562 | 0.1224 | 0.085* | |
C14 | 0.2836 (3) | 0.7587 (3) | 0.1305 (3) | 0.0533 (12) | |
C15 | −0.0254 (4) | 0.1144 (3) | 0.1001 (4) | 0.0978 (18) | |
H15A | −0.0039 | 0.0902 | 0.1652 | 0.147* | |
H15B | 0.0129 | 0.0829 | 0.0710 | 0.147* | |
H15C | −0.1022 | 0.1060 | 0.0591 | 0.147* | |
C16 | 0.5979 (3) | 0.2266 (3) | 0.0973 (3) | 0.0568 (12) | |
H16 | 0.6561 | 0.2098 | 0.0871 | 0.068* | |
C17 | 0.5683 (4) | 0.3173 (3) | 0.0901 (3) | 0.0652 (13) | |
H17 | 0.6067 | 0.3606 | 0.0746 | 0.078* | |
C18 | 0.4830 (4) | 0.3459 (3) | 0.1054 (3) | 0.0613 (12) | |
C19 | 0.4279 (4) | 0.2788 (3) | 0.1280 (3) | 0.0676 (13) | |
H19 | 0.3703 | 0.2959 | 0.1389 | 0.081* | |
C20 | 0.4557 (3) | 0.1880 (3) | 0.1346 (3) | 0.0606 (12) | |
H20 | 0.4164 | 0.1448 | 0.1493 | 0.073* | |
C21 | 0.5419 (3) | 0.1598 (3) | 0.1196 (3) | 0.0453 (11) | |
C22 | 0.5737 (3) | 0.0624 (3) | 0.1303 (3) | 0.0432 (10) | |
C23 | 0.6433 (3) | −0.0882 (3) | 0.1361 (3) | 0.0455 (10) | |
C24 | 0.6944 (3) | −0.1773 (3) | 0.1355 (3) | 0.0482 (11) | |
C25 | 0.6521 (3) | −0.2559 (3) | 0.1569 (3) | 0.0638 (13) | |
H25 | 0.5928 | −0.2502 | 0.1685 | 0.077* | |
C26 | 0.6957 (4) | −0.3413 (3) | 0.1612 (3) | 0.0753 (15) | |
H26 | 0.6664 | −0.3921 | 0.1766 | 0.090* | |
C27 | 0.7825 (4) | −0.3518 (3) | 0.1429 (3) | 0.0767 (15) | |
H27 | 0.8112 | −0.4097 | 0.1451 | 0.092* | |
C28 | 0.8264 (3) | −0.2767 (3) | 0.1213 (3) | 0.0671 (13) | |
H28 | 0.8858 | −0.2834 | 0.1098 | 0.080* | |
C29 | 0.7821 (3) | −0.1910 (3) | 0.1167 (3) | 0.0547 (12) | |
C30 | 0.4504 (4) | 0.4449 (3) | 0.0998 (3) | 0.0854 (16) | |
H30A | 0.4958 | 0.4818 | 0.0825 | 0.128* | |
H30B | 0.4587 | 0.4641 | 0.1632 | 0.128* | |
H30C | 0.3759 | 0.4519 | 0.0502 | 0.128* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0690 (8) | 0.0856 (10) | 0.1022 (10) | −0.0069 (7) | 0.0598 (8) | −0.0087 (8) |
Cl2 | 0.0796 (9) | 0.0713 (9) | 0.1322 (12) | 0.0056 (7) | 0.0757 (9) | 0.0044 (8) |
S1 | 0.0505 (7) | 0.0560 (8) | 0.0680 (8) | 0.0023 (6) | 0.0363 (7) | −0.0009 (6) |
S2 | 0.0560 (7) | 0.0518 (7) | 0.0671 (8) | 0.0019 (6) | 0.0387 (7) | 0.0021 (6) |
N1 | 0.069 (3) | 0.054 (3) | 0.127 (4) | 0.000 (2) | 0.069 (3) | −0.005 (2) |
N2 | 0.063 (3) | 0.057 (3) | 0.116 (3) | 0.003 (2) | 0.061 (3) | 0.000 (2) |
N3 | 0.057 (2) | 0.055 (3) | 0.086 (3) | 0.004 (2) | 0.046 (2) | 0.008 (2) |
N4 | 0.068 (3) | 0.053 (3) | 0.098 (3) | 0.004 (2) | 0.058 (3) | 0.006 (2) |
C1 | 0.061 (3) | 0.064 (4) | 0.081 (4) | 0.000 (3) | 0.038 (3) | −0.004 (3) |
C2 | 0.086 (4) | 0.054 (4) | 0.082 (4) | 0.011 (3) | 0.040 (3) | −0.009 (3) |
C3 | 0.078 (4) | 0.056 (3) | 0.052 (3) | −0.003 (3) | 0.013 (3) | 0.007 (3) |
C4 | 0.065 (3) | 0.070 (4) | 0.078 (4) | −0.008 (3) | 0.037 (3) | 0.011 (3) |
C5 | 0.065 (3) | 0.054 (3) | 0.081 (4) | −0.001 (3) | 0.040 (3) | 0.008 (3) |
C6 | 0.040 (3) | 0.052 (3) | 0.040 (3) | 0.006 (2) | 0.014 (2) | 0.008 (2) |
C7 | 0.034 (2) | 0.053 (3) | 0.044 (2) | 0.006 (2) | 0.017 (2) | 0.008 (2) |
C8 | 0.036 (2) | 0.051 (3) | 0.045 (3) | 0.006 (2) | 0.018 (2) | 0.005 (2) |
C9 | 0.037 (3) | 0.057 (3) | 0.045 (3) | 0.001 (2) | 0.015 (2) | 0.004 (2) |
C10 | 0.056 (3) | 0.055 (3) | 0.085 (4) | 0.007 (3) | 0.033 (3) | 0.005 (3) |
C11 | 0.077 (4) | 0.053 (4) | 0.114 (5) | 0.002 (3) | 0.044 (4) | 0.003 (3) |
C12 | 0.077 (4) | 0.060 (4) | 0.095 (4) | −0.017 (3) | 0.028 (3) | 0.005 (3) |
C13 | 0.059 (3) | 0.078 (4) | 0.073 (4) | −0.015 (3) | 0.029 (3) | 0.005 (3) |
C14 | 0.049 (3) | 0.052 (3) | 0.051 (3) | −0.002 (2) | 0.018 (2) | 0.001 (2) |
C15 | 0.119 (4) | 0.057 (4) | 0.091 (4) | −0.011 (3) | 0.028 (4) | 0.000 (3) |
C16 | 0.064 (3) | 0.054 (3) | 0.062 (3) | 0.000 (3) | 0.038 (3) | −0.001 (3) |
C17 | 0.082 (4) | 0.053 (3) | 0.074 (4) | 0.000 (3) | 0.049 (3) | 0.001 (3) |
C18 | 0.078 (3) | 0.054 (3) | 0.051 (3) | 0.007 (3) | 0.030 (3) | 0.000 (3) |
C19 | 0.063 (3) | 0.067 (4) | 0.080 (4) | 0.018 (3) | 0.039 (3) | 0.000 (3) |
C20 | 0.053 (3) | 0.064 (3) | 0.074 (3) | 0.005 (3) | 0.037 (3) | 0.003 (3) |
C21 | 0.044 (3) | 0.053 (3) | 0.034 (3) | 0.007 (2) | 0.014 (2) | −0.001 (2) |
C22 | 0.032 (2) | 0.057 (3) | 0.037 (2) | −0.003 (2) | 0.014 (2) | −0.004 (2) |
C23 | 0.040 (2) | 0.050 (3) | 0.041 (3) | −0.008 (2) | 0.015 (2) | −0.005 (2) |
C24 | 0.042 (3) | 0.050 (3) | 0.040 (3) | −0.005 (2) | 0.009 (2) | −0.002 (2) |
C25 | 0.052 (3) | 0.058 (3) | 0.074 (4) | 0.001 (3) | 0.024 (3) | 0.003 (3) |
C26 | 0.075 (4) | 0.047 (3) | 0.090 (4) | −0.004 (3) | 0.027 (3) | 0.006 (3) |
C27 | 0.071 (4) | 0.055 (3) | 0.092 (4) | 0.019 (3) | 0.028 (3) | −0.001 (3) |
C28 | 0.053 (3) | 0.061 (3) | 0.079 (4) | 0.012 (3) | 0.024 (3) | −0.004 (3) |
C29 | 0.043 (3) | 0.062 (3) | 0.056 (3) | 0.001 (2) | 0.020 (2) | −0.001 (2) |
C30 | 0.114 (4) | 0.062 (3) | 0.087 (4) | 0.023 (3) | 0.053 (3) | 0.007 (3) |
Cl1—C14 | 1.734 (4) | C12—H12 | 0.9300 |
Cl2—C29 | 1.738 (4) | C13—C14 | 1.399 (5) |
S1—C7 | 1.717 (4) | C13—H13 | 0.9300 |
S1—C8 | 1.727 (4) | C15—H15A | 0.9600 |
S2—C22 | 1.723 (4) | C15—H15B | 0.9600 |
S2—C23 | 1.723 (4) | C15—H15C | 0.9600 |
N1—C8 | 1.304 (4) | C16—C17 | 1.377 (5) |
N1—N2 | 1.380 (4) | C16—C21 | 1.390 (5) |
N2—C7 | 1.286 (4) | C16—H16 | 0.9300 |
N3—C22 | 1.307 (5) | C17—C18 | 1.382 (5) |
N3—N4 | 1.372 (4) | C17—H17 | 0.9300 |
N4—C23 | 1.302 (4) | C18—C19 | 1.386 (6) |
C1—C6 | 1.375 (5) | C18—C30 | 1.507 (5) |
C1—C2 | 1.397 (6) | C19—C20 | 1.371 (5) |
C1—H1 | 0.9300 | C19—H19 | 0.9300 |
C2—C3 | 1.376 (6) | C20—C21 | 1.390 (5) |
C2—H2 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.371 (6) | C21—C22 | 1.476 (5) |
C3—C15 | 1.509 (6) | C23—C24 | 1.487 (5) |
C4—C5 | 1.370 (6) | C24—C29 | 1.398 (5) |
C4—H4 | 0.9300 | C24—C25 | 1.398 (5) |
C5—C6 | 1.390 (5) | C25—C26 | 1.375 (5) |
C5—H5 | 0.9300 | C25—H25 | 0.9300 |
C6—C7 | 1.472 (5) | C26—C27 | 1.375 (5) |
C8—C9 | 1.472 (5) | C26—H26 | 0.9300 |
C9—C14 | 1.390 (5) | C27—C28 | 1.370 (6) |
C9—C10 | 1.402 (5) | C27—H27 | 0.9300 |
C10—C11 | 1.376 (5) | C28—C29 | 1.383 (5) |
C10—H10 | 0.9300 | C28—H28 | 0.9300 |
C11—C12 | 1.366 (6) | C30—H30A | 0.9600 |
C11—H11 | 0.9300 | C30—H30B | 0.9600 |
C12—C13 | 1.375 (6) | C30—H30C | 0.9600 |
C7—S1—C8 | 87.9 (2) | C3—C15—H15C | 109.5 |
C22—S2—C23 | 87.7 (2) | H15A—C15—H15C | 109.5 |
C8—N1—N2 | 113.3 (3) | H15B—C15—H15C | 109.5 |
C7—N2—N1 | 112.6 (3) | C17—C16—C21 | 120.8 (4) |
C22—N3—N4 | 112.2 (3) | C17—C16—H16 | 119.6 |
C23—N4—N3 | 113.7 (3) | C21—C16—H16 | 119.6 |
C6—C1—C2 | 120.5 (4) | C16—C17—C18 | 121.8 (4) |
C6—C1—H1 | 119.8 | C16—C17—H17 | 119.1 |
C2—C1—H1 | 119.8 | C18—C17—H17 | 119.1 |
C3—C2—C1 | 121.7 (4) | C17—C18—C19 | 117.0 (4) |
C3—C2—H2 | 119.1 | C17—C18—C30 | 122.8 (4) |
C1—C2—H2 | 119.1 | C19—C18—C30 | 120.3 (4) |
C4—C3—C2 | 116.8 (5) | C20—C19—C18 | 122.0 (4) |
C4—C3—C15 | 122.0 (5) | C20—C19—H19 | 119.0 |
C2—C3—C15 | 121.2 (5) | C18—C19—H19 | 119.0 |
C5—C4—C3 | 122.7 (5) | C19—C20—C21 | 120.7 (4) |
C5—C4—H4 | 118.7 | C19—C20—H20 | 119.6 |
C3—C4—H4 | 118.7 | C21—C20—H20 | 119.6 |
C4—C5—C6 | 120.6 (4) | C16—C21—C20 | 117.7 (4) |
C4—C5—H5 | 119.7 | C16—C21—C22 | 121.9 (4) |
C6—C5—H5 | 119.7 | C20—C21—C22 | 120.4 (4) |
C1—C6—C5 | 117.8 (4) | N3—C22—C21 | 121.9 (3) |
C1—C6—C7 | 122.2 (4) | N3—C22—S2 | 113.5 (3) |
C5—C6—C7 | 120.0 (4) | C21—C22—S2 | 124.6 (3) |
N2—C7—C6 | 122.8 (4) | N4—C23—C24 | 119.6 (4) |
N2—C7—S1 | 113.9 (3) | N4—C23—S2 | 112.9 (3) |
C6—C7—S1 | 123.3 (3) | C24—C23—S2 | 127.6 (3) |
N1—C8—C9 | 119.4 (4) | C29—C24—C25 | 116.0 (4) |
N1—C8—S1 | 112.4 (3) | C29—C24—C23 | 126.6 (4) |
C9—C8—S1 | 128.3 (3) | C25—C24—C23 | 117.3 (4) |
C14—C9—C10 | 117.2 (4) | C26—C25—C24 | 121.9 (4) |
C14—C9—C8 | 125.5 (4) | C26—C25—H25 | 119.0 |
C10—C9—C8 | 117.4 (4) | C24—C25—H25 | 119.0 |
C11—C10—C9 | 121.4 (4) | C25—C26—C27 | 120.2 (4) |
C11—C10—H10 | 119.3 | C25—C26—H26 | 119.9 |
C9—C10—H10 | 119.3 | C27—C26—H26 | 119.9 |
C12—C11—C10 | 120.4 (5) | C28—C27—C26 | 119.9 (4) |
C12—C11—H11 | 119.8 | C28—C27—H27 | 120.1 |
C10—C11—H11 | 119.8 | C26—C27—H27 | 120.1 |
C11—C12—C13 | 120.1 (5) | C27—C28—C29 | 119.7 (4) |
C11—C12—H12 | 119.9 | C27—C28—H28 | 120.1 |
C13—C12—H12 | 119.9 | C29—C28—H28 | 120.1 |
C12—C13—C14 | 119.8 (4) | C28—C29—C24 | 122.2 (4) |
C12—C13—H13 | 120.1 | C28—C29—Cl2 | 116.8 (3) |
C14—C13—H13 | 120.1 | C24—C29—Cl2 | 120.9 (3) |
C9—C14—C13 | 121.1 (4) | C18—C30—H30A | 109.5 |
C9—C14—Cl1 | 122.2 (3) | C18—C30—H30B | 109.5 |
C13—C14—Cl1 | 116.7 (4) | H30A—C30—H30B | 109.5 |
C3—C15—H15A | 109.5 | C18—C30—H30C | 109.5 |
C3—C15—H15B | 109.5 | H30A—C30—H30C | 109.5 |
H15A—C15—H15B | 109.5 | H30B—C30—H30C | 109.5 |
C8—N1—N2—C7 | 0.5 (5) | C12—C13—C14—Cl1 | −179.2 (4) |
C22—N3—N4—C23 | −1.2 (5) | C21—C16—C17—C18 | 0.5 (7) |
C6—C1—C2—C3 | 0.0 (7) | C16—C17—C18—C19 | −0.3 (6) |
C1—C2—C3—C4 | 0.8 (7) | C16—C17—C18—C30 | 178.9 (4) |
C1—C2—C3—C15 | −178.6 (4) | C17—C18—C19—C20 | −0.3 (7) |
C2—C3—C4—C5 | −1.0 (7) | C30—C18—C19—C20 | −179.4 (4) |
C15—C3—C4—C5 | 178.4 (4) | C18—C19—C20—C21 | 0.6 (7) |
C3—C4—C5—C6 | 0.3 (7) | C17—C16—C21—C20 | −0.3 (6) |
C2—C1—C6—C5 | −0.7 (6) | C17—C16—C21—C22 | −178.4 (4) |
C2—C1—C6—C7 | 179.5 (4) | C19—C20—C21—C16 | −0.3 (6) |
C4—C5—C6—C1 | 0.5 (6) | C19—C20—C21—C22 | 177.8 (4) |
C4—C5—C6—C7 | −179.7 (4) | N4—N3—C22—C21 | 179.9 (3) |
N1—N2—C7—C6 | 179.4 (4) | N4—N3—C22—S2 | 0.7 (5) |
N1—N2—C7—S1 | 0.1 (5) | C16—C21—C22—N3 | 171.8 (4) |
C1—C6—C7—N2 | −177.3 (4) | C20—C21—C22—N3 | −6.3 (6) |
C5—C6—C7—N2 | 2.9 (6) | C16—C21—C22—S2 | −9.1 (5) |
C1—C6—C7—S1 | 2.0 (6) | C20—C21—C22—S2 | 172.8 (3) |
C5—C6—C7—S1 | −177.8 (3) | C23—S2—C22—N3 | −0.1 (3) |
C8—S1—C7—N2 | −0.4 (3) | C23—S2—C22—C21 | −179.3 (3) |
C8—S1—C7—C6 | −179.8 (3) | N3—N4—C23—C24 | −179.5 (3) |
N2—N1—C8—C9 | 179.2 (4) | N3—N4—C23—S2 | 1.1 (4) |
N2—N1—C8—S1 | −0.8 (5) | C22—S2—C23—N4 | −0.6 (3) |
C7—S1—C8—N1 | 0.7 (3) | C22—S2—C23—C24 | −180.0 (4) |
C7—S1—C8—C9 | −179.3 (4) | N4—C23—C24—C29 | −171.7 (4) |
N1—C8—C9—C14 | 177.1 (4) | S2—C23—C24—C29 | 7.7 (6) |
S1—C8—C9—C14 | −2.8 (6) | N4—C23—C24—C25 | 7.6 (5) |
N1—C8—C9—C10 | −3.2 (6) | S2—C23—C24—C25 | −173.1 (3) |
S1—C8—C9—C10 | 176.8 (3) | C29—C24—C25—C26 | 1.3 (6) |
C14—C9—C10—C11 | −1.3 (7) | C23—C24—C25—C26 | −178.0 (4) |
C8—C9—C10—C11 | 179.1 (4) | C24—C25—C26—C27 | −0.9 (7) |
C9—C10—C11—C12 | 0.9 (7) | C25—C26—C27—C28 | 0.7 (7) |
C10—C11—C12—C13 | 0.0 (7) | C26—C27—C28—C29 | −1.0 (7) |
C11—C12—C13—C14 | −0.4 (7) | C27—C28—C29—C24 | 1.4 (7) |
C10—C9—C14—C13 | 0.8 (6) | C27—C28—C29—Cl2 | −179.5 (3) |
C8—C9—C14—C13 | −179.5 (4) | C25—C24—C29—C28 | −1.5 (6) |
C10—C9—C14—Cl1 | 180.0 (3) | C23—C24—C29—C28 | 177.7 (4) |
C8—C9—C14—Cl1 | −0.4 (6) | C25—C24—C29—Cl2 | 179.4 (3) |
C12—C13—C14—C9 | 0.0 (7) | C23—C24—C29—Cl2 | −1.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···N4i | 0.93 | 2.53 | 3.388 (8) | 153 |
C28—H28···N1ii | 0.93 | 2.49 | 3.303 (7) | 146 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y−1, z. |