| Literature DB >> 22259436 |
Islam Ullah Khan, Tahir Ali Sheikh, William T A Harrison.
Abstract
In the title compound, C(24)H(24)Cl(4)N(2)O(4)S(2), the dihedral angles between the central benzene ring and the pendant rings are 58.09 (10) and 62.59 (10)°. The dihedral angle between the pendant rings is 81.64 (9)°. Both sulfonamide groups lie to the same side of the central ring but the C-S-N-C torsion angles [73.09 (16) and -117.35 (14)] and S-N-C-C torsion angles [-143.80 (14) and -111.45 (16)°] differ significantly for the two pendant chains. The N atoms are close to planar (bond angle sums = 356.4 and 359.5°). In the crystal, weak C-H⋯O and C-H⋯Cl inter-actions link the mol-ecules.Entities:
Year: 2011 PMID: 22259436 PMCID: PMC3254356 DOI: 10.1107/S1600536811045326
Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN: 1600-5368
| C24H24Cl4N2O4S2 | |
| Triclinic, | |
| Hall symbol: -P 1 | Mo |
| Cell parameters from 6905 reflections | |
| θ = 2.2–28.1° | |
| µ = 0.61 mm−1 | |
| α = 87.454 (1)° | |
| β = 83.378 (1)° | Chnnk, colourless |
| γ = 87.995 (1)° | 0.50 × 0.35 × 0.30 mm |
| Bruker APEXII CCD diffractometer | 5380 reflections with |
| Radiation source: fine-focus sealed tube | |
| graphite | θmax = 28.4°, θmin = 3.0° |
| ω scans | |
| 25271 measured reflections | |
| 6905 independent reflections |
| Refinement on | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| Hydrogen site location: inferred from neighbouring sites | |
| H-atom parameters constrained | |
| 6905 reflections | (Δ/σ)max = 0.001 |
| 327 parameters | Δρmax = 0.47 e Å−3 |
| 0 restraints | Δρmin = −0.38 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 |
| C1 | 0.6756 (2) | 0.63163 (16) | 0.43821 (11) | 0.0454 (4) | |
| H1 | 0.5623 | 0.6242 | 0.4333 | 0.055* | |
| C2 | 0.7280 (3) | 0.63672 (17) | 0.51940 (12) | 0.0502 (4) | |
| C3 | 0.8970 (3) | 0.6480 (2) | 0.52549 (15) | 0.0695 (6) | |
| H3 | 0.9340 | 0.6525 | 0.5797 | 0.083* | |
| C4 | 1.0103 (3) | 0.6527 (3) | 0.45304 (17) | 0.0776 (7) | |
| H4 | 1.1236 | 0.6594 | 0.4583 | 0.093* | |
| C5 | 0.9572 (3) | 0.6475 (2) | 0.37192 (14) | 0.0622 (5) | |
| H5 | 1.0347 | 0.6509 | 0.3228 | 0.075* | |
| C6 | 0.7890 (2) | 0.63737 (16) | 0.36384 (11) | 0.0452 (4) | |
| C7 | 0.6016 (3) | 0.63174 (18) | 0.59876 (12) | 0.0579 (5) | |
| H7A | 0.4935 | 0.6113 | 0.5825 | 0.069* | |
| H7B | 0.6359 | 0.5696 | 0.6392 | 0.069* | |
| C8 | 0.5407 (3) | 0.85534 (19) | 0.58997 (13) | 0.0571 (5) | |
| H8A | 0.6171 | 0.8607 | 0.5371 | 0.069* | |
| H8B | 0.5553 | 0.9256 | 0.6225 | 0.069* | |
| C9 | 0.3646 (4) | 0.8577 (3) | 0.5668 (2) | 0.0967 (9) | |
| H9A | 0.3463 | 0.9274 | 0.5304 | 0.145* | |
| H9B | 0.2875 | 0.8603 | 0.6187 | 0.145* | |
| H9C | 0.3473 | 0.7867 | 0.5367 | 0.145* | |
| C10 | 0.75316 (19) | 0.69614 (16) | 0.77750 (10) | 0.0395 (3) | |
| C11 | 0.8994 (2) | 0.75963 (17) | 0.75576 (12) | 0.0462 (4) | |
| C12 | 1.0466 (2) | 0.71855 (19) | 0.78590 (14) | 0.0567 (5) | |
| H12 | 1.1438 | 0.7614 | 0.7717 | 0.068* | |
| C13 | 1.0506 (2) | 0.6145 (2) | 0.83684 (14) | 0.0578 (5) | |
| H13 | 1.1499 | 0.5873 | 0.8574 | 0.069* | |
| C14 | 0.9069 (2) | 0.55140 (17) | 0.85701 (12) | 0.0476 (4) | |
| C15 | 0.7572 (2) | 0.59124 (16) | 0.82812 (11) | 0.0417 (4) | |
| H15 | 0.6605 | 0.5479 | 0.8426 | 0.050* | |
| C16 | 0.7269 (2) | 0.63890 (16) | 0.27608 (11) | 0.0462 (4) | |
| H16A | 0.8216 | 0.6338 | 0.2317 | 0.055* | |
| H16B | 0.6586 | 0.5697 | 0.2724 | 0.055* | |
| C17 | 0.7074 (3) | 0.86554 (18) | 0.26202 (15) | 0.0604 (5) | |
| H17A | 0.7458 | 0.8739 | 0.3182 | 0.073* | |
| H17B | 0.6251 | 0.9295 | 0.2538 | 0.073* | |
| C18 | 0.8521 (4) | 0.8787 (3) | 0.1935 (2) | 0.0934 (9) | |
| H18A | 0.8894 | 0.9598 | 0.1910 | 0.140* | |
| H18B | 0.8181 | 0.8602 | 0.1386 | 0.140* | |
| H18C | 0.9419 | 0.8246 | 0.2069 | 0.140* | |
| C19 | 0.4012 (2) | 0.80340 (16) | 0.14908 (10) | 0.0414 (4) | |
| C20 | 0.4657 (2) | 0.74445 (17) | 0.07480 (11) | 0.0470 (4) | |
| C21 | 0.4306 (3) | 0.7893 (2) | −0.00540 (12) | 0.0597 (5) | |
| H21 | 0.4722 | 0.7489 | −0.0547 | 0.072* | |
| C22 | 0.3354 (3) | 0.8928 (2) | −0.01335 (13) | 0.0620 (5) | |
| H22 | 0.3119 | 0.9223 | −0.0676 | 0.074* | |
| C23 | 0.2751 (2) | 0.95234 (18) | 0.05987 (12) | 0.0514 (4) | |
| C24 | 0.3068 (2) | 0.90861 (17) | 0.14088 (11) | 0.0458 (4) | |
| H24 | 0.2649 | 0.9497 | 0.1898 | 0.055* | |
| S1 | 0.55636 (5) | 0.74464 (4) | 0.74476 (3) | 0.04106 (11) | |
| S2 | 0.42957 (6) | 0.74915 (4) | 0.25594 (3) | 0.04402 (11) | |
| N1 | 0.5864 (2) | 0.74805 (14) | 0.64078 (9) | 0.0489 (4) | |
| N2 | 0.62753 (19) | 0.74925 (13) | 0.26098 (10) | 0.0475 (3) | |
| O1 | 0.51855 (17) | 0.86403 (12) | 0.77167 (9) | 0.0560 (3) | |
| O2 | 0.44311 (14) | 0.65269 (12) | 0.77704 (8) | 0.0515 (3) | |
| O3 | 0.37690 (17) | 0.62781 (12) | 0.26631 (9) | 0.0563 (3) | |
| O4 | 0.34712 (19) | 0.83655 (14) | 0.31150 (8) | 0.0622 (4) | |
| Cl1 | 0.90284 (7) | 0.88984 (5) | 0.69119 (4) | 0.06287 (14) | |
| Cl2 | 0.91046 (7) | 0.41825 (5) | 0.91822 (4) | 0.06768 (16) | |
| Cl3 | 0.59191 (7) | 0.61629 (5) | 0.07875 (3) | 0.06285 (15) | |
| Cl4 | 0.15880 (8) | 1.08554 (5) | 0.05174 (4) | 0.07195 (17) |
| C1 | 0.0522 (10) | 0.0428 (10) | 0.0418 (9) | −0.0030 (7) | −0.0065 (7) | −0.0035 (7) |
| C2 | 0.0699 (12) | 0.0418 (10) | 0.0399 (9) | 0.0025 (8) | −0.0106 (8) | −0.0043 (7) |
| C3 | 0.0735 (14) | 0.0824 (16) | 0.0571 (13) | 0.0149 (12) | −0.0270 (11) | −0.0146 (11) |
| C4 | 0.0519 (12) | 0.107 (2) | 0.0773 (16) | 0.0142 (12) | −0.0204 (11) | −0.0194 (14) |
| C5 | 0.0492 (11) | 0.0776 (15) | 0.0591 (12) | 0.0081 (10) | −0.0047 (9) | −0.0072 (11) |
| C6 | 0.0494 (9) | 0.0430 (10) | 0.0429 (9) | 0.0052 (7) | −0.0054 (7) | −0.0032 (7) |
| C7 | 0.0879 (15) | 0.0477 (11) | 0.0384 (9) | −0.0080 (10) | −0.0066 (9) | −0.0019 (8) |
| C8 | 0.0692 (13) | 0.0528 (11) | 0.0463 (10) | 0.0054 (9) | −0.0006 (9) | 0.0103 (9) |
| C9 | 0.0856 (19) | 0.106 (2) | 0.099 (2) | 0.0127 (16) | −0.0304 (16) | 0.0276 (18) |
| C10 | 0.0340 (7) | 0.0486 (10) | 0.0360 (8) | −0.0002 (7) | −0.0017 (6) | −0.0088 (7) |
| C11 | 0.0416 (9) | 0.0473 (10) | 0.0486 (10) | −0.0037 (7) | 0.0021 (7) | −0.0083 (8) |
| C12 | 0.0345 (8) | 0.0634 (13) | 0.0716 (13) | −0.0056 (8) | −0.0007 (8) | −0.0081 (10) |
| C13 | 0.0368 (9) | 0.0688 (13) | 0.0688 (13) | 0.0047 (8) | −0.0101 (8) | −0.0098 (10) |
| C14 | 0.0446 (9) | 0.0508 (11) | 0.0478 (10) | 0.0054 (8) | −0.0077 (7) | −0.0067 (8) |
| C15 | 0.0363 (8) | 0.0506 (10) | 0.0383 (8) | −0.0013 (7) | −0.0034 (6) | −0.0068 (7) |
| C16 | 0.0526 (10) | 0.0469 (10) | 0.0382 (9) | 0.0034 (8) | −0.0012 (7) | −0.0060 (7) |
| C17 | 0.0711 (13) | 0.0451 (11) | 0.0688 (13) | −0.0084 (9) | −0.0234 (11) | 0.0018 (9) |
| C18 | 0.098 (2) | 0.0845 (19) | 0.097 (2) | −0.0371 (16) | −0.0047 (16) | 0.0179 (16) |
| C19 | 0.0412 (8) | 0.0490 (10) | 0.0340 (8) | −0.0053 (7) | −0.0023 (6) | −0.0035 (7) |
| C20 | 0.0479 (9) | 0.0528 (11) | 0.0394 (9) | −0.0017 (8) | 0.0001 (7) | −0.0069 (8) |
| C21 | 0.0703 (13) | 0.0731 (14) | 0.0347 (9) | 0.0004 (11) | −0.0004 (8) | −0.0085 (9) |
| C22 | 0.0715 (13) | 0.0772 (15) | 0.0375 (10) | 0.0008 (11) | −0.0103 (9) | 0.0033 (9) |
| C23 | 0.0531 (10) | 0.0530 (11) | 0.0486 (10) | −0.0030 (8) | −0.0100 (8) | 0.0023 (8) |
| C24 | 0.0452 (9) | 0.0519 (11) | 0.0406 (9) | −0.0028 (8) | −0.0044 (7) | −0.0054 (8) |
| S1 | 0.0364 (2) | 0.0499 (3) | 0.0361 (2) | 0.00241 (17) | −0.00185 (15) | −0.00196 (17) |
| S2 | 0.0484 (2) | 0.0491 (3) | 0.0329 (2) | −0.00132 (18) | 0.00197 (16) | −0.00125 (17) |
| N1 | 0.0683 (10) | 0.0431 (8) | 0.0353 (7) | 0.0015 (7) | −0.0079 (7) | 0.0006 (6) |
| N2 | 0.0529 (8) | 0.0411 (8) | 0.0501 (8) | −0.0039 (6) | −0.0123 (7) | −0.0002 (6) |
| O1 | 0.0568 (8) | 0.0580 (8) | 0.0521 (8) | 0.0143 (6) | −0.0022 (6) | −0.0118 (6) |
| O2 | 0.0339 (6) | 0.0686 (9) | 0.0508 (7) | −0.0053 (6) | −0.0034 (5) | 0.0098 (6) |
| O3 | 0.0571 (8) | 0.0549 (8) | 0.0549 (8) | −0.0138 (6) | 0.0022 (6) | 0.0074 (6) |
| O4 | 0.0727 (9) | 0.0730 (10) | 0.0378 (7) | 0.0149 (7) | 0.0046 (6) | −0.0090 (6) |
| Cl1 | 0.0584 (3) | 0.0556 (3) | 0.0720 (3) | −0.0115 (2) | 0.0042 (2) | 0.0037 (2) |
| Cl2 | 0.0640 (3) | 0.0647 (3) | 0.0758 (4) | 0.0053 (2) | −0.0212 (3) | 0.0105 (3) |
| Cl3 | 0.0713 (3) | 0.0645 (3) | 0.0507 (3) | 0.0141 (3) | 0.0007 (2) | −0.0128 (2) |
| Cl4 | 0.0829 (4) | 0.0666 (4) | 0.0675 (3) | 0.0136 (3) | −0.0205 (3) | 0.0039 (3) |
| C1—C2 | 1.382 (2) | C14—C15 | 1.385 (2) |
| C1—C6 | 1.389 (3) | C14—Cl2 | 1.730 (2) |
| C1—H1 | 0.9300 | C15—H15 | 0.9300 |
| C2—C3 | 1.383 (3) | C16—N2 | 1.468 (2) |
| C2—C7 | 1.507 (3) | C16—H16A | 0.9700 |
| C3—C4 | 1.366 (3) | C16—H16B | 0.9700 |
| C3—H3 | 0.9300 | C17—N2 | 1.469 (2) |
| C4—C5 | 1.383 (3) | C17—C18 | 1.491 (4) |
| C4—H4 | 0.9300 | C17—H17A | 0.9700 |
| C5—C6 | 1.381 (3) | C17—H17B | 0.9700 |
| C5—H5 | 0.9300 | C18—H18A | 0.9600 |
| C6—C16 | 1.507 (2) | C18—H18B | 0.9600 |
| C7—N1 | 1.474 (2) | C18—H18C | 0.9600 |
| C7—H7A | 0.9700 | C19—C24 | 1.384 (2) |
| C7—H7B | 0.9700 | C19—C20 | 1.394 (2) |
| C8—N1 | 1.465 (2) | C19—S2 | 1.7820 (17) |
| C8—C9 | 1.499 (3) | C20—C21 | 1.380 (3) |
| C8—H8A | 0.9700 | C20—Cl3 | 1.726 (2) |
| C8—H8B | 0.9700 | C21—C22 | 1.371 (3) |
| C9—H9A | 0.9600 | C21—H21 | 0.9300 |
| C9—H9B | 0.9600 | C22—C23 | 1.376 (3) |
| C9—H9C | 0.9600 | C22—H22 | 0.9300 |
| C10—C15 | 1.383 (2) | C23—C24 | 1.380 (3) |
| C10—C11 | 1.394 (2) | C23—Cl4 | 1.735 (2) |
| C10—S1 | 1.7769 (16) | C24—H24 | 0.9300 |
| C11—C12 | 1.379 (3) | S1—O1 | 1.4256 (14) |
| C11—Cl1 | 1.7282 (19) | S1—O2 | 1.4307 (13) |
| C12—C13 | 1.378 (3) | S1—N1 | 1.6082 (15) |
| C12—H12 | 0.9300 | S2—O4 | 1.4267 (14) |
| C13—C14 | 1.372 (3) | S2—O3 | 1.4286 (14) |
| C13—H13 | 0.9300 | S2—N2 | 1.6025 (16) |
| C2—C1—C6 | 121.26 (18) | N2—C16—C6 | 110.74 (14) |
| C2—C1—H1 | 119.4 | N2—C16—H16A | 109.5 |
| C6—C1—H1 | 119.4 | C6—C16—H16A | 109.5 |
| C1—C2—C3 | 118.56 (19) | N2—C16—H16B | 109.5 |
| C1—C2—C7 | 119.97 (19) | C6—C16—H16B | 109.5 |
| C3—C2—C7 | 121.47 (18) | H16A—C16—H16B | 108.1 |
| C4—C3—C2 | 120.9 (2) | N2—C17—C18 | 112.5 (2) |
| C4—C3—H3 | 119.6 | N2—C17—H17A | 109.1 |
| C2—C3—H3 | 119.6 | C18—C17—H17A | 109.1 |
| C3—C4—C5 | 120.3 (2) | N2—C17—H17B | 109.1 |
| C3—C4—H4 | 119.8 | C18—C17—H17B | 109.1 |
| C5—C4—H4 | 119.8 | H17A—C17—H17B | 107.8 |
| C6—C5—C4 | 120.1 (2) | C17—C18—H18A | 109.5 |
| C6—C5—H5 | 120.0 | C17—C18—H18B | 109.5 |
| C4—C5—H5 | 120.0 | H18A—C18—H18B | 109.5 |
| C5—C6—C1 | 118.91 (17) | C17—C18—H18C | 109.5 |
| C5—C6—C16 | 121.04 (17) | H18A—C18—H18C | 109.5 |
| C1—C6—C16 | 119.97 (16) | H18B—C18—H18C | 109.5 |
| N1—C7—C2 | 110.85 (16) | C24—C19—C20 | 119.20 (16) |
| N1—C7—H7A | 109.5 | C24—C19—S2 | 117.24 (13) |
| C2—C7—H7A | 109.5 | C20—C19—S2 | 123.55 (14) |
| N1—C7—H7B | 109.5 | C21—C20—C19 | 119.87 (18) |
| C2—C7—H7B | 109.5 | C21—C20—Cl3 | 117.85 (15) |
| H7A—C7—H7B | 108.1 | C19—C20—Cl3 | 122.28 (14) |
| N1—C8—C9 | 114.22 (19) | C22—C21—C20 | 120.85 (19) |
| N1—C8—H8A | 108.7 | C22—C21—H21 | 119.6 |
| C9—C8—H8A | 108.7 | C20—C21—H21 | 119.6 |
| N1—C8—H8B | 108.7 | C21—C22—C23 | 119.20 (18) |
| C9—C8—H8B | 108.7 | C21—C22—H22 | 120.4 |
| H8A—C8—H8B | 107.6 | C23—C22—H22 | 120.4 |
| C8—C9—H9A | 109.5 | C22—C23—C24 | 121.06 (19) |
| C8—C9—H9B | 109.5 | C22—C23—Cl4 | 120.31 (15) |
| H9A—C9—H9B | 109.5 | C24—C23—Cl4 | 118.63 (16) |
| C8—C9—H9C | 109.5 | C23—C24—C19 | 119.79 (17) |
| H9A—C9—H9C | 109.5 | C23—C24—H24 | 120.1 |
| H9B—C9—H9C | 109.5 | C19—C24—H24 | 120.1 |
| C15—C10—C11 | 119.74 (15) | O1—S1—O2 | 118.08 (8) |
| C15—C10—S1 | 117.14 (12) | O1—S1—N1 | 108.23 (8) |
| C11—C10—S1 | 123.11 (14) | O2—S1—N1 | 110.99 (8) |
| C12—C11—C10 | 119.87 (18) | O1—S1—C10 | 109.11 (8) |
| C12—C11—Cl1 | 118.30 (15) | O2—S1—C10 | 105.20 (8) |
| C10—C11—Cl1 | 121.83 (14) | N1—S1—C10 | 104.35 (8) |
| C13—C12—C11 | 120.47 (18) | O4—S2—O3 | 118.77 (9) |
| C13—C12—H12 | 119.8 | O4—S2—N2 | 109.82 (9) |
| C11—C12—H12 | 119.8 | O3—S2—N2 | 108.25 (8) |
| C14—C13—C12 | 119.45 (18) | O4—S2—C19 | 105.17 (9) |
| C14—C13—H13 | 120.3 | O3—S2—C19 | 108.50 (8) |
| C12—C13—H13 | 120.3 | N2—S2—C19 | 105.53 (8) |
| C13—C14—C15 | 121.21 (18) | C8—N1—C7 | 118.50 (15) |
| C13—C14—Cl2 | 120.22 (15) | C8—N1—S1 | 120.83 (13) |
| C15—C14—Cl2 | 118.56 (15) | C7—N1—S1 | 117.12 (12) |
| C10—C15—C14 | 119.25 (16) | C16—N2—C17 | 118.81 (16) |
| C10—C15—H15 | 120.4 | C16—N2—S2 | 122.54 (12) |
| C14—C15—H15 | 120.4 | C17—N2—S2 | 118.14 (13) |
| C6—C1—C2—C3 | 0.1 (3) | C22—C23—C24—C19 | 0.2 (3) |
| C6—C1—C2—C7 | 179.28 (17) | Cl4—C23—C24—C19 | −179.11 (14) |
| C1—C2—C3—C4 | −0.7 (3) | C20—C19—C24—C23 | 1.3 (3) |
| C7—C2—C3—C4 | −179.9 (2) | S2—C19—C24—C23 | −177.43 (14) |
| C2—C3—C4—C5 | 0.7 (4) | C15—C10—S1—O1 | 124.12 (14) |
| C3—C4—C5—C6 | −0.1 (4) | C11—C10—S1—O1 | −54.76 (16) |
| C4—C5—C6—C1 | −0.5 (3) | C15—C10—S1—O2 | −3.50 (15) |
| C4—C5—C6—C16 | 176.4 (2) | C11—C10—S1—O2 | 177.63 (14) |
| C2—C1—C6—C5 | 0.5 (3) | C15—C10—S1—N1 | −120.40 (14) |
| C2—C1—C6—C16 | −176.41 (17) | C11—C10—S1—N1 | 60.73 (16) |
| C1—C2—C7—N1 | −111.1 (2) | C24—C19—S2—O4 | −2.36 (16) |
| C3—C2—C7—N1 | 68.0 (2) | C20—C19—S2—O4 | 178.98 (15) |
| C15—C10—C11—C12 | −1.0 (3) | C24—C19—S2—O3 | 125.71 (14) |
| S1—C10—C11—C12 | 177.85 (15) | C20—C19—S2—O3 | −52.96 (17) |
| C15—C10—C11—Cl1 | 178.88 (13) | C24—C19—S2—N2 | −118.46 (14) |
| S1—C10—C11—Cl1 | −2.3 (2) | C20—C19—S2—N2 | 62.87 (17) |
| C10—C11—C12—C13 | 0.5 (3) | C9—C8—N1—C7 | 68.6 (3) |
| Cl1—C11—C12—C13 | −179.33 (16) | C9—C8—N1—S1 | −89.6 (2) |
| C11—C12—C13—C14 | 0.4 (3) | C2—C7—N1—C8 | 57.3 (2) |
| C12—C13—C14—C15 | −0.9 (3) | C2—C7—N1—S1 | −143.80 (14) |
| C12—C13—C14—Cl2 | 178.11 (16) | O1—S1—N1—C8 | −12.41 (18) |
| C11—C10—C15—C14 | 0.5 (3) | O2—S1—N1—C8 | 118.67 (16) |
| S1—C10—C15—C14 | −178.43 (13) | C10—S1—N1—C8 | −128.51 (16) |
| C13—C14—C15—C10 | 0.5 (3) | O1—S1—N1—C7 | −170.82 (15) |
| Cl2—C14—C15—C10 | −178.57 (13) | O2—S1—N1—C7 | −39.74 (17) |
| C5—C6—C16—N2 | −111.2 (2) | C10—S1—N1—C7 | 73.09 (16) |
| C1—C6—C16—N2 | 65.6 (2) | C6—C16—N2—C17 | 60.2 (2) |
| C24—C19—C20—C21 | −2.0 (3) | C6—C16—N2—S2 | −111.45 (16) |
| S2—C19—C20—C21 | 176.64 (16) | C18—C17—N2—C16 | 61.4 (2) |
| C24—C19—C20—Cl3 | 177.23 (14) | C18—C17—N2—S2 | −126.57 (19) |
| S2—C19—C20—Cl3 | −4.1 (2) | O4—S2—N2—C16 | 129.76 (14) |
| C19—C20—C21—C22 | 1.2 (3) | O3—S2—N2—C16 | −1.35 (16) |
| Cl3—C20—C21—C22 | −178.04 (17) | C19—S2—N2—C16 | −117.35 (14) |
| C20—C21—C22—C23 | 0.3 (3) | O4—S2—N2—C17 | −41.94 (17) |
| C21—C22—C23—C24 | −1.0 (3) | O3—S2—N2—C17 | −173.06 (14) |
| C21—C22—C23—Cl4 | 178.31 (17) | C19—S2—N2—C17 | 70.94 (16) |
| H··· | ||||
| C7—H7B···O3i | 0.97 | 2.59 | 3.511 (2) | 158 |
| C17—H17B···O1ii | 0.97 | 2.58 | 3.516 (3) | 164 |
| C24—H24···Cl1ii | 0.93 | 2.83 | 3.738 (2) | 166 |
Hydrogen-bond geometry (Å, °)
| H⋯ | ||||
|---|---|---|---|---|
| C7—H7 | 0.97 | 2.59 | 3.511 (2) | 158 |
| C17—H17 | 0.97 | 2.58 | 3.516 (3) | 164 |
| C24—H24⋯Cl1ii | 0.93 | 2.83 | 3.738 (2) | 166 |
Symmetry codes: (i) ; (ii) .