Acta Cryst. (2009). E65, o272 [ doi:10.1107/S1600536808043419 ]
In the title compound, C25H21Cl2NO2S3, the three phenyl rings are inclined to each other at dihedral angles of 68.4 (1), 79.5 (1) and 37.0 (1)°.
2-Nitropentachlorobutadiene (2.0 g, 7.37 mmol) and benzyl mercaptan (2.74 g, 22.11 mmol) were mixed in ethanol(30 ml), 2 g of NaOH (in 10 ml of water) was added at room temperature. The mixture was stirred for 2–3 h. Chloroform was added to the reaction mixture. The organic layer was separated and washed with water (4 x 30 ml) and dried with Na2SO4. After the solvent had evaporated, the residue was purified by column chromatography on silica gel. Yellow crystals of (I) suitable for X-ray diffraction analysis were obtained by slow evaporation of an ethanol at room temperature (yield: 0.76 g, 20%; m.p. 357–358 K).
H atoms were treated as riding, with C—H = 0.95 (6)Å and Uiso(H) = 1.2Ueq(C). Refinement used 6597 reflections with F2 >3.0σ(F2).
Data collection: PROCESS (Rigaku, 1996); cell refinement: PROCESS (Rigaku, 1996); data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2003).
![[Figure 1]](./xu2466fig1thm.gif)
| Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. |
| C25H21Cl2NO2S3 | Z = 2 |
| Mr = 534.53 | F(000) = 552.00 |
| Triclinic, P1 | Dx = 1.392 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
| a = 10.1595 (10) Å | Cell parameters from 10024 reflections |
| b = 11.5706 (10) Å | θ = 2.2–30.5° |
| c = 12.5451 Å | µ = 0.52 mm−1 |
| α = 74.887 (6)° | T = 293 K |
| β = 69.259 (5)° | Prism, yellow |
| γ = 69.344 (5)° | 0.60 × 0.60 × 0.10 mm |
| V = 1274.83 (2) Å3 |
| Rigaku R-AXIS diffractometer | 7264 reflections with F2 > 2.0σ(F2) |
| Detector resolution: 10.00 pixels mm-1 | Rint = 0.024 |
| ω scans | θmax = 30.3° |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→14 |
| Tmin = 0.731, Tmax = 0.949 | k = −16→16 |
| 101262 measured reflections | l = −17→17 |
| 7512 independent reflections |
| Refinement on F | All H-atom parameters refined |
| R[F2 > 2σ(F2)] = 0.066 | Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 1.8080 -4.9818 -0.4430 |
| wR(F2) = 0.045 | (Δ/σ)max < 0.001 |
| S = 1.20 | Δρmax = 0.31 e Å−3 |
| 6957 reflections | Δρmin = −0.34 e Å−3 |
| 319 parameters |
| C25H21Cl2NO2S3 | γ = 69.344 (5)° |
| Mr = 534.53 | V = 1274.83 (2) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 10.1595 (10) Å | Mo Kα radiation |
| b = 11.5706 (10) Å | µ = 0.52 mm−1 |
| c = 12.5451 Å | T = 293 K |
| α = 74.887 (6)° | 0.60 × 0.60 × 0.10 mm |
| β = 69.259 (5)° |
| Rigaku R-AXIS diffractometer | 7512 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 7264 reflections with F2 > 2.0σ(F2) |
| Tmin = 0.731, Tmax = 0.949 | Rint = 0.024 |
| 101262 measured reflections | θmax = 30.3° |
| R[F2 > 2σ(F2)] = 0.066 | All H-atom parameters refined |
| wR(F2) = 0.045 | Δρmax = 0.31 e Å−3 |
| S = 1.20 | Δρmin = −0.34 e Å−3 |
| 6957 reflections | Absolute structure: ? |
| 319 parameters | Flack parameter: ? |
| ? restraints | Rogers parameter: ? |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 sigma(F2) is used only for calculating R-factor (gt). |
| x | y | z | Uiso*/Ueq | ||
| S(1) | 0.26233 (3) | −0.27301 (2) | 0.14860 (2) | 0.06102 (8) | |
| S(2) | 0.51264 (3) | −0.16364 (2) | −0.00818 (2) | 0.05869 (7) | |
| S(3) | 0.32274 (3) | −0.18195 (2) | 0.43976 (2) | 0.05472 (7) | |
| Cl(2) | 0.46317 (4) | −0.52367 (3) | 0.29977 (3) | 0.08279 (10) | |
| Cl(1) | 0.29918 (3) | −0.45732 (3) | 0.52456 (2) | 0.07867 (9) | |
| O(2) | 0.69150 (9) | −0.31748 (10) | 0.25152 (9) | 0.1049 (3) | |
| C(3) | 0.46483 (10) | −0.24924 (8) | 0.22255 (7) | 0.0452 (2) | |
| N(1) | 0.60515 (10) | −0.23115 (9) | 0.21164 (7) | 0.0599 (3) | |
| C(6) | 0.06852 (11) | −0.03451 (9) | 0.12175 (8) | 0.0554 (3) | |
| C(2) | 0.38853 (10) | −0.29043 (8) | 0.34376 (8) | 0.0472 (2) | |
| C(12) | 0.53745 (12) | −0.27616 (9) | −0.09776 (8) | 0.0656 (3) | |
| C(4) | 0.41789 (10) | −0.22722 (8) | 0.12919 (8) | 0.0467 (2) | |
| O(1) | 0.62431 (12) | −0.12993 (9) | 0.16884 (9) | 0.1054 (4) | |
| C(5) | 0.15905 (13) | −0.14498 (10) | 0.06169 (9) | 0.0679 (3) | |
| C(19) | 0.2622 (1) | −0.03352 (10) | 0.35006 (10) | 0.0723 (3) | |
| C(25) | 0.09262 (11) | 0.13681 (10) | 0.46338 (9) | 0.0611 (3) | |
| C(1) | 0.38339 (11) | −0.40762 (9) | 0.38298 (8) | 0.0545 (3) | |
| C(24) | 0.0636 (1) | 0.22953 (11) | 0.52495 (11) | 0.0740 (4) | |
| C(7) | 0.11962 (13) | 0.06683 (10) | 0.10021 (10) | 0.0685 (4) | |
| C(13) | 0.68084 (11) | −0.37659 (8) | −0.10637 (8) | 0.0571 (3) | |
| C(11) | −0.0680 (1) | −0.03113 (11) | 0.19867 (10) | 0.0769 (4) | |
| C(22) | 0.3176 (2) | 0.18959 (12) | 0.49366 (13) | 0.0873 (5) | |
| C(20) | 0.23412 (11) | 0.06770 (9) | 0.41576 (8) | 0.0562 (3) | |
| C(21) | 0.34768 (12) | 0.09577 (10) | 0.43161 (11) | 0.0728 (4) | |
| C(23) | 0.1763 (2) | 0.25476 (11) | 0.54108 (12) | 0.0851 (5) | |
| C(18) | 0.7057 (2) | −0.45940 (10) | −0.00968 (10) | 0.0802 (4) | |
| C(8) | 0.0382 (2) | 0.16857 (11) | 0.1559 (1) | 0.0899 (5) | |
| C(14) | 0.7909 (2) | −0.38460 (12) | −0.21024 (13) | 0.0853 (4) | |
| C(10) | −0.1501 (2) | 0.0705 (2) | 0.25525 (12) | 0.1016 (5) | |
| C(9) | −0.0961 (2) | 0.1699 (1) | 0.23337 (13) | 0.1019 (6) | |
| C(15) | 0.9252 (2) | −0.4770 (2) | −0.2127 (2) | 0.1179 (7) | |
| C(16) | 0.9462 (2) | −0.5565 (2) | −0.1155 (2) | 0.1120 (7) | |
| C(17) | 0.8397 (2) | −0.54888 (13) | −0.0147 (2) | 0.1095 (6) | |
| H(1) | 0.22499 (13) | −0.12013 (10) | −0.00917 (9) | 0.0843 (11)* | |
| H(2) | 0.09310 (13) | −0.17564 (10) | 0.04664 (9) | 0.0847 (10)* | |
| H(3) | 0.21293 (13) | 0.06651 (10) | 0.04609 (10) | 0.0850 (11)* | |
| H(4) | 0.0744 (2) | 0.23844 (11) | 0.1398 (1) | 0.1130 (11)* | |
| H(5) | −0.1524 (2) | 0.2386 (1) | 0.27395 (13) | 0.1181 (11)* | |
| H(6) | −0.2439 (2) | 0.0719 (2) | 0.30899 (12) | 0.1091 (11)* | |
| H(7) | −0.1066 (1) | −0.09929 (11) | 0.21298 (10) | 0.0912 (10)* | |
| H(8) | 0.46109 (12) | −0.31533 (9) | −0.06329 (8) | 0.0781 (10)* | |
| H(9) | 0.53273 (12) | −0.23380 (9) | −0.17275 (8) | 0.0787 (10)* | |
| H(10) | 0.7753 (2) | −0.32952 (12) | −0.27839 (13) | 0.0981 (11)* | |
| H(11) | 1.0029 (2) | −0.4859 (2) | −0.2826 (2) | 0.1339 (12)* | |
| H(12) | 1.0384 (2) | −0.6175 (2) | −0.1177 (2) | 0.1381 (13)* | |
| H(13) | 0.8561 (2) | −0.60471 (13) | 0.0529 (2) | 0.1335 (12)* | |
| H(14) | 0.6289 (2) | −0.45517 (10) | 0.06095 (10) | 0.0920 (11)* | |
| H(15) | 0.3368 (1) | −0.02515 (10) | 0.27928 (10) | 0.0850 (11)* | |
| H(16) | 0.1750 (1) | −0.02808 (10) | 0.33470 (10) | 0.0850 (10)* | |
| H(17) | 0.44699 (12) | 0.05170 (10) | 0.39823 (11) | 0.0860 (10)* | |
| H(18) | 0.3949 (2) | 0.20947 (12) | 0.50400 (13) | 0.1159 (11)* | |
| H(19) | 0.1562 (2) | 0.31794 (11) | 0.58487 (12) | 0.1074 (11)* | |
| H(20) | −0.0344 (1) | 0.27810 (11) | 0.55578 (11) | 0.0867 (10)* | |
| H(21) | 0.01245 (11) | 0.12000 (10) | 0.45437 (9) | 0.0742 (10)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S(1) | 0.0677 (2) | 0.0591 (1) | 0.0658 (2) | −0.02160 (13) | −0.03755 (13) | 0.00494 (12) |
| S(2) | 0.0776 (2) | 0.04780 (13) | 0.04488 (13) | −0.01718 (12) | −0.01546 (12) | −0.00220 (10) |
| S(3) | 0.0585 (2) | 0.0586 (1) | 0.04394 (12) | −0.01226 (12) | −0.01779 (11) | −0.00514 (10) |
| Cl(2) | 0.1318 (3) | 0.0530 (2) | 0.0759 (2) | −0.0324 (2) | −0.0456 (2) | −0.00051 (13) |
| Cl(1) | 0.0866 (2) | 0.0846 (2) | 0.0624 (2) | −0.0428 (2) | −0.0246 (2) | 0.0219 (1) |
| O(2) | 0.0538 (5) | 0.1180 (7) | 0.1299 (8) | −0.0190 (5) | −0.0382 (5) | 0.0103 (6) |
| C(3) | 0.0499 (5) | 0.0443 (5) | 0.0433 (5) | −0.0151 (4) | −0.0167 (4) | −0.0032 (4) |
| N(1) | 0.0611 (6) | 0.0762 (6) | 0.0486 (5) | −0.0301 (5) | −0.0156 (4) | −0.0060 (4) |
| C(6) | 0.0617 (6) | 0.0606 (6) | 0.0490 (5) | −0.0159 (5) | −0.0324 (5) | 0.0034 (4) |
| C(2) | 0.0495 (5) | 0.0522 (5) | 0.0437 (5) | −0.0175 (4) | −0.0209 (4) | 0.0006 (4) |
| C(12) | 0.0761 (7) | 0.0714 (7) | 0.0485 (5) | −0.0072 (6) | −0.0254 (5) | −0.0173 (5) |
| C(4) | 0.0551 (5) | 0.0391 (4) | 0.0458 (5) | −0.0092 (4) | −0.0202 (4) | −0.0046 (4) |
| O(1) | 0.1254 (8) | 0.1100 (7) | 0.1164 (8) | −0.0819 (7) | −0.0554 (6) | 0.0196 (6) |
| C(5) | 0.0762 (7) | 0.0702 (7) | 0.0646 (6) | −0.0093 (6) | −0.0437 (6) | −0.0063 (5) |
| C(19) | 0.0924 (8) | 0.0576 (6) | 0.0612 (6) | −0.0034 (6) | −0.0362 (6) | −0.0061 (5) |
| C(25) | 0.0547 (6) | 0.0614 (6) | 0.0680 (7) | −0.0163 (5) | −0.0222 (5) | −0.0060 (5) |
| C(1) | 0.0628 (6) | 0.0574 (5) | 0.0510 (5) | −0.0262 (5) | −0.0259 (5) | 0.0047 (4) |
| C(24) | 0.0758 (8) | 0.0658 (7) | 0.0726 (7) | −0.0105 (6) | −0.0203 (6) | −0.0137 (6) |
| C(7) | 0.0747 (7) | 0.0637 (7) | 0.0750 (7) | −0.0182 (6) | −0.0414 (6) | 0.0018 (6) |
| C(13) | 0.0680 (6) | 0.0514 (5) | 0.0573 (6) | −0.0148 (5) | −0.0236 (5) | −0.0131 (5) |
| C(11) | 0.0743 (8) | 0.0828 (9) | 0.0686 (7) | −0.0280 (7) | −0.0222 (7) | 0.0061 (7) |
| C(22) | 0.0925 (10) | 0.0800 (8) | 0.1155 (11) | −0.0402 (8) | −0.0592 (9) | 0.0043 (8) |
| C(20) | 0.0606 (6) | 0.0549 (5) | 0.0545 (6) | −0.0151 (5) | −0.0243 (5) | −0.0022 (5) |
| C(21) | 0.0542 (7) | 0.0724 (7) | 0.0888 (8) | −0.0151 (5) | −0.0306 (6) | 0.0018 (6) |
| C(23) | 0.1182 (12) | 0.0600 (7) | 0.0887 (9) | −0.0220 (8) | −0.0474 (9) | −0.0114 (6) |
| C(18) | 0.1006 (10) | 0.0645 (7) | 0.0645 (7) | −0.0003 (7) | −0.0297 (7) | −0.0169 (6) |
| C(8) | 0.1181 (12) | 0.0659 (8) | 0.0985 (10) | −0.0148 (8) | −0.0651 (10) | −0.0030 (7) |
| C(14) | 0.0885 (9) | 0.0708 (8) | 0.0861 (9) | −0.0348 (7) | 0.0043 (7) | −0.0205 (7) |
| C(10) | 0.0850 (10) | 0.1219 (13) | 0.0632 (8) | −0.0115 (9) | −0.0092 (7) | −0.0005 (9) |
| C(9) | 0.137 (2) | 0.0843 (10) | 0.0741 (9) | 0.0060 (10) | −0.0504 (10) | −0.0200 (8) |
| C(15) | 0.0842 (11) | 0.0939 (11) | 0.155 (2) | −0.0424 (10) | 0.0290 (11) | −0.0525 (12) |
| C(16) | 0.0712 (10) | 0.0860 (11) | 0.189 (2) | −0.0078 (8) | −0.0403 (12) | −0.0548 (13) |
| C(17) | 0.1273 (13) | 0.0714 (9) | 0.135 (2) | 0.0171 (9) | −0.0780 (13) | −0.0317 (9) |
| S(1)—C(4) | 1.757 (1) | C(24)—C(23) | 1.367 (3) |
| S(1)—C(5) | 1.832 (1) | C(24)—H(20) | 0.950 (2) |
| S(2)—C(12) | 1.831 (1) | C(7)—C(8) | 1.375 (2) |
| S(2)—C(4) | 1.7610 (9) | C(7)—H(3) | 0.950 (2) |
| S(3)—C(2) | 1.760 (1) | C(13)—C(18) | 1.376 (1) |
| S(3)—C(19) | 1.825 (1) | C(13)—C(14) | 1.384 (2) |
| Cl(2)—C(1) | 1.707 (1) | C(11)—C(10) | 1.381 (2) |
| Cl(1)—C(1) | 1.7192 (9) | C(11)—H(7) | 0.950 (2) |
| O(2)—N(1) | 1.204 (1) | C(22)—C(21) | 1.384 (2) |
| C(3)—N(1) | 1.467 (2) | C(22)—C(23) | 1.359 (2) |
| C(3)—C(2) | 1.479 (1) | C(22)—H(18) | 0.950 (3) |
| C(3)—C(4) | 1.348 (2) | C(20)—C(21) | 1.392 (2) |
| N(1)—O(1) | 1.207 (1) | C(21)—H(17) | 0.950 (1) |
| C(6)—C(5) | 1.493 (1) | C(23)—H(19) | 0.950 (2) |
| C(6)—C(7) | 1.372 (2) | C(18)—C(17) | 1.381 (2) |
| C(6)—C(11) | 1.375 (1) | C(18)—H(14) | 0.950 (2) |
| C(2)—C(1) | 1.329 (1) | C(8)—C(9) | 1.364 (2) |
| C(12)—C(13) | 1.498 (1) | C(8)—H(4) | 0.950 (2) |
| C(12)—H(8) | 0.950 (2) | C(14)—C(15) | 1.401 (2) |
| C(12)—H(9) | 0.950 (1) | C(14)—H(10) | 0.950 (2) |
| C(5)—H(1) | 0.950 (1) | C(10)—C(9) | 1.368 (3) |
| C(5)—H(2) | 0.950 (2) | C(10)—H(6) | 0.950 (2) |
| C(19)—C(20) | 1.494 (2) | C(9)—H(5) | 0.950 (2) |
| C(19)—H(15) | 0.950 (2) | C(15)—C(16) | 1.355 (3) |
| C(19)—H(16) | 0.950 (2) | C(15)—H(11) | 0.950 (3) |
| C(25)—C(24) | 1.372 (2) | C(16)—C(17) | 1.341 (3) |
| C(25)—C(20) | 1.376 (1) | C(16)—H(12) | 0.950 (2) |
| C(25)—H(21) | 0.950 (2) | C(17)—H(13) | 0.950 (3) |
| S(1)···S(2) | 3.0605 (4) | C(21)···H(10)ii | 3.029 (2) |
| S(1)···Cl(2) | 3.4452 (4) | C(21)···H(15) | 2.697 (2) |
| S(1)···C(3) | 2.656 (1) | C(21)···H(16) | 3.287 (2) |
| S(1)···C(6) | 2.7852 (9) | C(21)···H(18) | 2.040 (2) |
| S(1)···C(2) | 3.076 (1) | C(21)···H(19) | 3.239 (2) |
| S(1)···C(12) | 3.3517 (9) | C(21)···H(21) | 3.231 (2) |
| S(1)···C(5) | 1.832 (1) | C(23)···C(25) | 2.374 (2) |
| S(1)···C(1) | 3.377 (1) | C(23)···C(20) | 2.779 (2) |
| S(1)···C(11) | 3.505 (1) | C(23)···C(21) | 2.380 (2) |
| S(1)···C(16)i | 3.542 (2) | C(23)···H(10)ii | 3.085 (2) |
| S(1)···C(17)i | 3.562 (3) | C(23)···H(17) | 3.231 (2) |
| S(1)···H(1) | 2.329 (1) | C(23)···H(18) | 1.999 (2) |
| S(1)···H(2) | 2.302 (1) | C(23)···H(20) | 2.007 (2) |
| S(1)···H(7) | 3.483 (1) | C(23)···H(21) | 3.223 (2) |
| S(1)···H(8) | 2.7500 (9) | C(18)···S(2) | 3.291 (1) |
| S(1)···H(14) | 3.506 (1) | C(18)···C(12) | 2.490 (2) |
| S(2)···S(1) | 3.0605 (4) | C(18)···C(4) | 3.477 (1) |
| S(2)···C(3) | 2.7284 (8) | C(18)···C(14) | 2.383 (2) |
| S(2)···N(1) | 3.048 (1) | C(18)···C(15) | 2.725 (2) |
| S(2)···C(12) | 1.831 (1) | C(18)···C(16) | 2.353 (2) |
| S(2)···O(1) | 2.987 (1) | C(18)···H(8) | 2.662 (2) |
| S(2)···O(1)ii | 3.5522 (9) | C(18)···H(8)i | 3.358 (2) |
| S(2)···C(5) | 3.323 (1) | C(18)···H(9) | 3.258 (2) |
| S(2)···C(13) | 2.7622 (9) | C(18)···H(10) | 3.247 (2) |
| S(2)···C(18) | 3.291 (1) | C(18)···H(12) | 3.208 (2) |
| S(2)···H(1) | 2.789 (1) | C(18)···H(13) | 2.031 (2) |
| S(2)···H(3) | 3.253 (1) | C(8)···C(6) | 2.392 (2) |
| S(2)···H(3)ii | 3.202 (2) | C(8)···C(11) | 2.737 (2) |
| S(2)···H(8) | 2.317 (1) | C(8)···C(10) | 2.368 (2) |
| S(2)···H(9) | 2.328 (1) | C(8)···H(2)iv | 3.233 (3) |
| S(2)···H(14) | 3.149 (1) | C(8)···H(3) | 2.020 (2) |
| S(3)···Cl(1) | 3.1514 (4) | C(8)···H(5) | 2.021 (2) |
| S(3)···C(3) | 2.7645 (9) | C(8)···H(6) | 3.224 (2) |
| S(3)···N(1) | 3.2600 (8) | C(8)···H(16) | 3.075 (2) |
| S(3)···C(19) | 1.825 (1) | C(8)···H(21) | 3.566 (2) |
| S(3)···C(1) | 2.689 (1) | C(14)···C(12) | 2.503 (2) |
| S(3)···C(20) | 2.674 (1) | C(14)···C(18) | 2.383 (2) |
| S(3)···C(21) | 3.284 (1) | C(14)···C(16) | 2.395 (2) |
| S(3)···H(15) | 2.332 (1) | C(14)···C(17) | 2.764 (2) |
| S(3)···H(16) | 2.335 (1) | C(14)···H(4)ii | 2.963 (3) |
| S(3)···H(17) | 3.222 (1) | C(14)···H(8) | 3.125 (2) |
| Cl(2)···S(1) | 3.4452 (4) | C(14)···H(9) | 2.544 (2) |
| Cl(2)···Cl(1) | 2.8664 (4) | C(14)···H(11) | 2.056 (2) |
| Cl(2)···C(3) | 3.073 (1) | C(14)···H(12) | 3.254 (2) |
| Cl(2)···C(2) | 2.683 (1) | C(14)···H(14) | 3.238 (2) |
| Cl(2)···C(4) | 3.5090 (9) | C(10)···C(6) | 2.395 (2) |
| Cl(2)···H(9)i | 3.552 (1) | C(10)···C(7) | 2.735 (2) |
| Cl(2)···H(10)i | 3.526 (2) | C(10)···C(8) | 2.368 (2) |
| Cl(2)···H(14) | 2.927 (1) | C(10)···H(1)iv | 3.297 (2) |
| Cl(2)···H(18)iii | 3.565 (1) | C(10)···H(2)iv | 3.564 (2) |
| Cl(1)···S(3) | 3.1514 (4) | C(10)···H(4) | 3.225 (3) |
| Cl(1)···Cl(2) | 2.8664 (4) | C(10)···H(5) | 2.010 (3) |
| Cl(1)···C(2) | 2.6818 (9) | C(10)···H(7) | 2.025 (2) |
| Cl(1)···H(19)iii | 3.210 (2) | C(10)···H(16) | 3.505 (2) |
| O(2)···C(3) | 2.285 (1) | C(9)···C(6) | 2.762 (2) |
| O(2)···C(2) | 2.810 (1) | C(9)···C(7) | 2.370 (2) |
| O(2)···C(4) | 3.363 (2) | C(9)···C(11) | 2.377 (2) |
| O(2)···O(1) | 2.129 (1) | C(9)···H(2)iv | 3.485 (2) |
| O(2)···C(1) | 3.370 (1) | C(9)···H(3) | 3.225 (2) |
| O(2)···H(14) | 3.527 (2) | C(9)···H(4) | 2.013 (3) |
| C(3)···S(1) | 2.656 (1) | C(9)···H(6) | 2.018 (3) |
| C(3)···S(2) | 2.7284 (8) | C(9)···H(7) | 3.232 (2) |
| C(3)···S(3) | 2.7645 (9) | C(9)···H(16) | 3.310 (2) |
| C(3)···Cl(2) | 3.073 (1) | C(9)···H(21) | 3.181 (2) |
| C(3)···O(2) | 2.285 (1) | C(15)···C(13) | 2.391 (2) |
| C(3)···O(1) | 2.303 (2) | C(15)···C(18) | 2.725 (2) |
| C(3)···C(19) | 3.025 (1) | C(15)···C(17) | 2.349 (3) |
| C(3)···C(1) | 2.462 (1) | C(15)···H(4)ii | 3.128 (3) |
| C(3)···H(14) | 3.145 (1) | C(15)···H(10) | 2.057 (2) |
| C(3)···H(15) | 2.617 (1) | C(15)···H(12) | 2.007 (3) |
| C(3)···H(16) | 3.290 (1) | C(15)···H(13) | 3.206 (3) |
| N(1)···S(2) | 3.048 (1) | C(16)···S(1)i | 3.542 (2) |
| N(1)···S(3) | 3.2600 (8) | C(16)···C(13) | 2.749 (2) |
| N(1)···C(2) | 2.439 (1) | C(16)···C(18) | 2.353 (2) |
| N(1)···C(4) | 2.449 (2) | C(16)···C(14) | 2.395 (2) |
| N(1)···C(19) | 3.542 (1) | C(16)···H(2)i | 3.121 (2) |
| N(1)···C(1) | 3.375 (1) | C(16)···H(4)ii | 3.549 (2) |
| N(1)···H(3)ii | 3.541 (1) | C(16)···H(10) | 3.253 (2) |
| N(1)···H(14) | 3.484 (2) | C(16)···H(11) | 1.993 (3) |
| N(1)···H(15) | 2.943 (1) | C(16)···H(13) | 1.997 (3) |
| C(6)···S(1) | 2.7852 (9) | C(16)···H(14) | 3.209 (2) |
| C(6)···C(6)iv | 3.587 (2) | C(17)···S(1)i | 3.562 (3) |
| C(6)···C(4) | 3.482 (1) | C(17)···C(13) | 2.398 (2) |
| C(6)···C(5)iv | 3.584 (2) | C(17)···C(14) | 2.764 (2) |
| C(6)···C(8) | 2.392 (2) | C(17)···C(15) | 2.349 (3) |
| C(6)···C(10) | 2.395 (2) | C(17)···H(2)i | 3.118 (2) |
| C(6)···C(9) | 2.762 (2) | C(17)···H(4)vi | 3.485 (3) |
| C(6)···H(1) | 2.023 (1) | C(17)···H(11) | 3.194 (3) |
| C(6)···H(1)iv | 3.463 (2) | C(17)···H(12) | 1.983 (2) |
| C(6)···H(2) | 1.991 (2) | C(17)···H(14) | 2.030 (2) |
| C(6)···H(2)iv | 3.167 (1) | H(1)···S(1) | 2.329 (1) |
| C(6)···H(3) | 2.016 (2) | H(1)···S(2) | 2.789 (1) |
| C(6)···H(4) | 3.247 (2) | H(1)···C(6) | 2.023 (1) |
| C(6)···H(6) | 3.252 (2) | H(1)···C(6)iv | 3.463 (2) |
| C(6)···H(7) | 2.022 (2) | H(1)···C(12) | 3.013 (1) |
| C(6)···H(16) | 3.243 (2) | H(1)···C(4) | 2.822 (2) |
| C(2)···S(1) | 3.076 (1) | H(1)···O(1)ii | 3.558 (2) |
| C(2)···Cl(2) | 2.683 (1) | H(1)···C(7) | 2.566 (2) |
| C(2)···Cl(1) | 2.6818 (9) | H(1)···C(11) | 3.234 (1) |
| C(2)···O(2) | 2.810 (1) | H(1)···C(11)iv | 3.131 (2) |
| C(2)···N(1) | 2.439 (1) | H(1)···C(10)iv | 3.297 (2) |
| C(2)···C(4) | 2.535 (1) | H(2)···S(1) | 2.302 (1) |
| C(2)···O(1) | 3.360 (1) | H(2)···C(6) | 1.991 (2) |
| C(2)···C(19) | 2.802 (1) | H(2)···C(6)iv | 3.167 (1) |
| C(2)···H(15) | 2.867 (1) | H(2)···C(7) | 3.169 (2) |
| C(2)···H(16) | 3.047 (1) | H(2)···C(7)iv | 3.056 (2) |
| C(12)···S(1) | 3.3517 (9) | H(2)···C(11) | 2.575 (2) |
| C(12)···S(2) | 1.831 (1) | H(2)···C(11)iv | 3.398 (2) |
| C(12)···C(4) | 2.794 (1) | H(2)···C(8)iv | 3.233 (3) |
| C(12)···C(18) | 2.490 (2) | H(2)···C(10)iv | 3.564 (2) |
| C(12)···C(14) | 2.503 (2) | H(2)···C(9)iv | 3.485 (2) |
| C(12)···H(1) | 3.013 (1) | H(2)···C(16)i | 3.121 (2) |
| C(12)···H(10) | 2.675 (2) | H(2)···C(17)i | 3.118 (2) |
| C(12)···H(14) | 2.630 (1) | H(3)···S(2) | 3.253 (1) |
| C(4)···Cl(2) | 3.5090 (9) | H(3)···S(2)ii | 3.202 (2) |
| C(4)···O(2) | 3.363 (2) | H(3)···N(1)ii | 3.541 (1) |
| C(4)···N(1) | 2.449 (2) | H(3)···C(6) | 2.016 (2) |
| C(4)···C(6) | 3.482 (1) | H(3)···C(4) | 3.416 (1) |
| C(4)···C(2) | 2.535 (1) | H(3)···O(1)ii | 2.685 (1) |
| C(4)···C(12) | 2.794 (1) | H(3)···C(5) | 2.635 (2) |
| C(4)···O(1) | 2.934 (2) | H(3)···C(11) | 3.219 (2) |
| C(4)···C(5) | 2.816 (2) | H(3)···C(8) | 2.020 (2) |
| C(4)···C(19) | 3.583 (2) | H(3)···C(9) | 3.225 (2) |
| C(4)···C(1) | 3.298 (1) | H(4)···C(6) | 3.247 (2) |
| C(4)···C(13) | 3.560 (1) | H(4)···C(7) | 2.027 (2) |
| C(4)···C(18) | 3.477 (1) | H(4)···C(13)ii | 3.260 (2) |
| C(4)···H(1) | 2.822 (2) | H(4)···C(14)ii | 2.963 (3) |
| C(4)···H(3) | 3.416 (1) | H(4)···C(10) | 3.225 (3) |
| C(4)···H(8) | 2.698 (2) | H(4)···C(9) | 2.013 (3) |
| C(4)···H(9) | 3.560 (1) | H(4)···C(15)ii | 3.128 (3) |
| C(4)···H(14) | 2.859 (1) | H(4)···C(16)ii | 3.549 (2) |
| C(4)···H(15) | 3.087 (2) | H(5)···C(7) | 3.233 (2) |
| C(4)···H(16) | 3.553 (1) | H(5)···C(11) | 3.232 (2) |
| O(1)···S(2) | 2.987 (1) | H(5)···C(8) | 2.021 (2) |
| O(1)···S(2)ii | 3.5522 (9) | H(5)···C(10) | 2.010 (3) |
| O(1)···O(2) | 2.129 (1) | H(6)···C(6) | 3.252 (2) |
| O(1)···C(3) | 2.303 (2) | H(6)···C(11) | 2.033 (2) |
| O(1)···C(2) | 3.360 (1) | H(6)···C(8) | 3.224 (2) |
| O(1)···C(4) | 2.934 (2) | H(6)···C(9) | 2.018 (3) |
| O(1)···C(19) | 3.528 (1) | H(7)···S(1) | 3.483 (1) |
| O(1)···C(7)ii | 3.540 (1) | H(7)···C(6) | 2.022 (2) |
| O(1)···H(1)ii | 3.558 (2) | H(7)···C(5) | 2.656 (2) |
| O(1)···H(3)ii | 2.685 (1) | H(7)···C(7) | 3.221 (2) |
| O(1)···H(7)v | 3.125 (2) | H(7)···C(10) | 2.025 (2) |
| O(1)···H(15) | 2.726 (1) | H(7)···C(9) | 3.232 (2) |
| O(1)···H(17) | 3.571 (2) | H(8)···S(1) | 2.7500 (9) |
| C(5)···S(1) | 1.832 (1) | H(8)···S(2) | 2.317 (1) |
| C(5)···S(2) | 3.323 (1) | H(8)···C(4) | 2.698 (2) |
| C(5)···C(6)iv | 3.584 (2) | H(8)···C(5) | 3.114 (1) |
| C(5)···C(4) | 2.816 (2) | H(8)···C(13) | 2.002 (1) |
| C(5)···C(7) | 2.488 (2) | H(8)···C(18) | 2.662 (2) |
| C(5)···C(11) | 2.498 (1) | H(8)···C(18)i | 3.358 (2) |
| C(5)···H(3) | 2.635 (2) | H(8)···C(14) | 3.125 (2) |
| C(5)···H(7) | 2.656 (2) | H(9)···S(2) | 2.328 (1) |
| C(5)···H(8) | 3.114 (1) | H(9)···Cl(2)i | 3.552 (1) |
| C(19)···S(3) | 1.825 (1) | H(9)···C(4) | 3.560 (1) |
| C(19)···C(3) | 3.025 (1) | H(9)···C(13) | 2.026 (1) |
| C(19)···N(1) | 3.542 (1) | H(9)···C(21)ii | 3.232 (1) |
| C(19)···C(2) | 2.802 (1) | H(9)···C(18) | 3.258 (2) |
| C(19)···C(4) | 3.583 (2) | H(9)···C(14) | 2.544 (2) |
| C(19)···O(1) | 3.528 (1) | H(10)···Cl(2)i | 3.526 (2) |
| C(19)···C(25) | 2.491 (1) | H(10)···C(12) | 2.675 (2) |
| C(19)···C(21) | 2.526 (2) | H(10)···C(25)ii | 3.060 (2) |
| C(19)···H(17) | 2.698 (2) | H(10)···C(24)ii | 3.077 (2) |
| C(19)···H(21) | 2.643 (1) | H(10)···C(13) | 2.041 (2) |
| C(25)···C(19) | 2.491 (1) | H(10)···C(22)ii | 3.042 (2) |
| C(25)···C(22) | 2.731 (2) | H(10)···C(20)ii | 3.057 (2) |
| C(25)···C(21) | 2.366 (2) | H(10)···C(21)ii | 3.029 (2) |
| C(25)···C(23) | 2.374 (2) | H(10)···C(23)ii | 3.085 (2) |
| C(25)···H(10)ii | 3.060 (2) | H(10)···C(18) | 3.247 (2) |
| C(25)···H(15) | 3.150 (1) | H(10)···C(15) | 2.057 (2) |
| C(25)···H(16) | 2.543 (2) | H(10)···C(16) | 3.253 (2) |
| C(25)···H(17) | 3.230 (2) | H(11)···C(13) | 3.257 (2) |
| C(25)···H(19) | 3.233 (2) | H(11)···C(14) | 2.056 (2) |
| C(25)···H(20) | 2.030 (2) | H(11)···C(16) | 1.993 (3) |
| C(1)···S(1) | 3.377 (1) | H(11)···C(17) | 3.194 (3) |
| C(1)···S(3) | 2.689 (1) | H(12)···C(18) | 3.208 (2) |
| C(1)···O(2) | 3.370 (1) | H(12)···C(14) | 3.254 (2) |
| C(1)···C(3) | 2.462 (1) | H(12)···C(15) | 2.007 (3) |
| C(1)···N(1) | 3.375 (1) | H(12)···C(17) | 1.983 (2) |
| C(1)···C(4) | 3.298 (1) | H(13)···C(13) | 3.253 (2) |
| C(24)···C(22) | 2.358 (2) | H(13)···C(18) | 2.031 (2) |
| C(24)···C(20) | 2.398 (1) | H(13)···C(8)vi | 2.911 (2) |
| C(24)···C(21) | 2.738 (1) | H(13)···C(9)vi | 2.995 (2) |
| C(24)···H(10)ii | 3.077 (2) | H(13)···C(15) | 3.206 (3) |
| C(24)···H(18) | 3.210 (2) | H(13)···C(16) | 1.997 (3) |
| C(24)···H(19) | 2.020 (3) | H(14)···S(1) | 3.506 (1) |
| C(24)···H(21) | 2.009 (2) | H(14)···S(2) | 3.149 (1) |
| C(7)···O(1)ii | 3.540 (1) | H(14)···Cl(2) | 2.927 (1) |
| C(7)···C(5) | 2.488 (2) | H(14)···O(2) | 3.527 (2) |
| C(7)···C(11) | 2.360 (2) | H(14)···C(3) | 3.145 (1) |
| C(7)···C(10) | 2.735 (2) | H(14)···N(1) | 3.484 (2) |
| C(7)···C(9) | 2.370 (2) | H(14)···C(12) | 2.630 (1) |
| C(7)···H(1) | 2.566 (2) | H(14)···C(4) | 2.859 (1) |
| C(7)···H(2) | 3.169 (2) | H(14)···C(13) | 2.017 (1) |
| C(7)···H(2)iv | 3.056 (2) | H(14)···C(14) | 3.238 (2) |
| C(7)···H(4) | 2.027 (2) | H(14)···C(16) | 3.209 (2) |
| C(7)···H(5) | 3.233 (2) | H(14)···C(17) | 2.030 (2) |
| C(7)···H(7) | 3.221 (2) | H(15)···S(3) | 2.332 (1) |
| C(7)···H(15) | 3.414 (2) | H(15)···C(3) | 2.617 (1) |
| C(7)···H(16) | 3.038 (2) | H(15)···N(1) | 2.943 (1) |
| C(13)···S(2) | 2.7622 (9) | H(15)···C(2) | 2.867 (1) |
| C(13)···C(4) | 3.560 (1) | H(15)···C(4) | 3.087 (2) |
| C(13)···C(15) | 2.391 (2) | H(15)···O(1) | 2.726 (1) |
| C(13)···C(16) | 2.749 (2) | H(15)···C(25) | 3.150 (1) |
| C(13)···C(17) | 2.398 (2) | H(15)···C(7) | 3.414 (2) |
| C(13)···H(4)ii | 3.260 (2) | H(15)···C(20) | 2.019 (2) |
| C(13)···H(8) | 2.002 (1) | H(15)···C(21) | 2.697 (2) |
| C(13)···H(9) | 2.026 (1) | H(16)···S(3) | 2.335 (1) |
| C(13)···H(10) | 2.041 (2) | H(16)···C(3) | 3.290 (1) |
| C(13)···H(11) | 3.257 (2) | H(16)···C(6) | 3.243 (2) |
| C(13)···H(13) | 3.253 (2) | H(16)···C(2) | 3.047 (1) |
| C(13)···H(14) | 2.017 (1) | H(16)···C(4) | 3.553 (1) |
| C(11)···S(1) | 3.505 (1) | H(16)···C(25) | 2.543 (2) |
| C(11)···C(5) | 2.498 (1) | H(16)···C(7) | 3.038 (2) |
| C(11)···C(7) | 2.360 (2) | H(16)···C(11) | 3.476 (2) |
| C(11)···C(8) | 2.737 (2) | H(16)···C(20) | 2.028 (2) |
| C(11)···C(9) | 2.377 (2) | H(16)···C(21) | 3.287 (2) |
| C(11)···H(1) | 3.234 (1) | H(16)···C(8) | 3.075 (2) |
| C(11)···H(1)iv | 3.131 (2) | H(16)···C(10) | 3.505 (2) |
| C(11)···H(2) | 2.575 (2) | H(16)···C(9) | 3.310 (2) |
| C(11)···H(2)iv | 3.398 (2) | H(17)···S(3) | 3.222 (1) |
| C(11)···H(3) | 3.219 (2) | H(17)···O(1) | 3.571 (2) |
| C(11)···H(5) | 3.232 (2) | H(17)···C(19) | 2.698 (2) |
| C(11)···H(6) | 2.033 (2) | H(17)···C(25) | 3.230 (2) |
| C(11)···H(16) | 3.476 (2) | H(17)···C(22) | 2.027 (2) |
| C(22)···C(25) | 2.731 (2) | H(17)···C(20) | 2.040 (2) |
| C(22)···C(24) | 2.358 (2) | H(17)···C(23) | 3.231 (2) |
| C(22)···C(20) | 2.411 (2) | H(18)···Cl(2)vii | 3.565 (1) |
| C(22)···H(10)ii | 3.042 (2) | H(18)···C(24) | 3.210 (2) |
| C(22)···H(17) | 2.027 (2) | H(18)···C(20) | 3.272 (2) |
| C(22)···H(19) | 2.010 (2) | H(18)···C(21) | 2.040 (2) |
| C(22)···H(20) | 3.210 (2) | H(18)···C(23) | 1.999 (2) |
| C(20)···S(3) | 2.674 (1) | H(19)···Cl(1)vii | 3.210 (2) |
| C(20)···C(24) | 2.398 (1) | H(19)···C(25) | 3.233 (2) |
| C(20)···C(22) | 2.411 (2) | H(19)···C(24) | 2.020 (3) |
| C(20)···C(23) | 2.779 (2) | H(19)···C(22) | 2.010 (2) |
| C(20)···H(10)ii | 3.057 (2) | H(19)···C(21) | 3.239 (2) |
| C(20)···H(15) | 2.019 (2) | H(20)···C(25) | 2.030 (2) |
| C(20)···H(16) | 2.028 (2) | H(20)···C(22) | 3.210 (2) |
| C(20)···H(17) | 2.040 (2) | H(20)···C(20) | 3.256 (1) |
| C(20)···H(18) | 3.272 (2) | H(20)···C(23) | 2.007 (2) |
| C(20)···H(20) | 3.256 (1) | H(21)···C(19) | 2.643 (1) |
| C(20)···H(21) | 2.023 (1) | H(21)···C(24) | 2.009 (2) |
| C(21)···S(3) | 3.284 (1) | H(21)···C(20) | 2.023 (1) |
| C(21)···C(19) | 2.526 (2) | H(21)···C(21) | 3.231 (2) |
| C(21)···C(25) | 2.366 (2) | H(21)···C(23) | 3.223 (2) |
| C(21)···C(24) | 2.738 (1) | H(21)···C(8) | 3.566 (2) |
| C(21)···C(23) | 2.380 (2) | H(21)···C(9) | 3.181 (2) |
| C(21)···H(9)ii | 3.232 (1) | ||
| C(4)—S(1)—C(5) | 103.34 (5) | C(8)—C(7)—H(3) | 119.5 (2) |
| C(12)—S(2)—C(4) | 102.13 (5) | C(8)—C(7)—C(6) | 121.1 (1) |
| C(2)—S(3)—C(19) | 102.76 (5) | H(3)—C(7)—C(6) | 119.4 (1) |
| N(1)—C(3)—C(2) | 111.76 (9) | C(18)—C(13)—C(14) | 119.4 (1) |
| N(1)—C(3)—C(4) | 120.85 (7) | C(18)—C(13)—C(12) | 119.99 (8) |
| C(2)—C(3)—C(4) | 127.4 (1) | C(14)—C(13)—C(12) | 120.55 (9) |
| O(1)—N(1)—O(2) | 124.0 (1) | C(10)—C(11)—H(7) | 119.5 (1) |
| O(1)—N(1)—C(3) | 118.61 (9) | C(10)—C(11)—C(6) | 120.8 (1) |
| O(2)—N(1)—C(3) | 117.2 (1) | H(7)—C(11)—C(6) | 119.7 (1) |
| C(5)—C(6)—C(7) | 120.45 (9) | C(21)—C(22)—C(23) | 120.4 (2) |
| C(5)—C(6)—C(11) | 121.1 (1) | C(21)—C(22)—H(18) | 120.7 (1) |
| C(7)—C(6)—C(11) | 118.5 (1) | C(23)—C(22)—H(18) | 118.9 (2) |
| C(1)—C(2)—S(3) | 120.32 (7) | C(21)—C(20)—C(19) | 122.12 (9) |
| C(1)—C(2)—C(3) | 122.36 (9) | C(21)—C(20)—C(25) | 117.5 (1) |
| S(3)—C(2)—C(3) | 116.89 (7) | C(19)—C(20)—C(25) | 120.4 (1) |
| C(13)—C(12)—H(8) | 107.6 (1) | H(17)—C(21)—C(22) | 119.4 (2) |
| C(13)—C(12)—H(9) | 109.7 (1) | H(17)—C(21)—C(20) | 120.0 (2) |
| C(13)—C(12)—S(2) | 111.76 (9) | C(22)—C(21)—C(20) | 120.6 (1) |
| H(8)—C(12)—H(9) | 109.5 (2) | H(19)—C(23)—C(24) | 120.2 (2) |
| H(8)—C(12)—S(2) | 108.71 (9) | H(19)—C(23)—C(22) | 120.0 (2) |
| H(9)—C(12)—S(2) | 109.6 (1) | C(24)—C(23)—C(22) | 119.8 (1) |
| S(1)—C(4)—S(2) | 120.88 (7) | C(17)—C(18)—H(14) | 120.0 (1) |
| S(1)—C(4)—C(3) | 116.92 (7) | C(17)—C(18)—C(13) | 120.9 (1) |
| S(2)—C(4)—C(3) | 122.11 (8) | H(14)—C(18)—C(13) | 119.2 (1) |
| H(1)—C(5)—H(2) | 109.5 (2) | C(9)—C(8)—H(4) | 119.9 (2) |
| H(1)—C(5)—S(1) | 109.6 (1) | C(9)—C(8)—C(7) | 119.9 (2) |
| H(1)—C(5)—C(6) | 109.8 (1) | H(4)—C(8)—C(7) | 120.3 (2) |
| H(2)—C(5)—S(1) | 107.4 (1) | C(15)—C(14)—H(10) | 120.9 (2) |
| H(2)—C(5)—C(6) | 107.1 (1) | C(15)—C(14)—C(13) | 118.3 (1) |
| S(1)—C(5)—C(6) | 113.40 (8) | H(10)—C(14)—C(13) | 120.8 (1) |
| C(20)—C(19)—H(15) | 109.4 (2) | C(9)—C(10)—H(6) | 119.9 (2) |
| C(20)—C(19)—H(16) | 110.1 (1) | C(9)—C(10)—C(11) | 119.7 (1) |
| C(20)—C(19)—S(3) | 106.89 (9) | H(6)—C(10)—C(11) | 120.4 (2) |
| H(15)—C(19)—H(16) | 109.5 (2) | H(5)—C(9)—C(8) | 120.7 (2) |
| H(15)—C(19)—S(3) | 110.4 (1) | H(5)—C(9)—C(10) | 119.1 (2) |
| H(16)—C(19)—S(3) | 110.6 (1) | C(8)—C(9)—C(10) | 120.1 (1) |
| C(24)—C(25)—C(20) | 121.6 (1) | C(16)—C(15)—H(11) | 118.6 (2) |
| C(24)—C(25)—H(21) | 118.7 (1) | C(16)—C(15)—C(14) | 120.7 (2) |
| C(20)—C(25)—H(21) | 119.7 (1) | H(11)—C(15)—C(14) | 120.7 (2) |
| Cl(2)—C(1)—Cl(1) | 113.58 (6) | C(17)—C(16)—H(12) | 118.8 (3) |
| Cl(2)—C(1)—C(2) | 123.70 (7) | C(17)—C(16)—C(15) | 121.2 (2) |
| Cl(1)—C(1)—C(2) | 122.70 (8) | H(12)—C(16)—C(15) | 120.0 (2) |
| C(23)—C(24)—H(20) | 119.0 (2) | H(13)—C(17)—C(18) | 120.1 (2) |
| C(23)—C(24)—C(25) | 120.2 (1) | H(13)—C(17)—C(16) | 120.3 (2) |
| H(20)—C(24)—C(25) | 120.9 (2) | C(18)—C(17)—C(16) | 119.6 (2) |
| C(5)—S(1)—C(4)—S(2) | −43.15 (6) | C(24)—C(25)—C(20)—C(19) | 179.43 (9) |
| C(5)—S(1)—C(4)—C(3) | 140.26 (6) | C(24)—C(25)—C(20)—C(21) | −0.4 (1) |
| C(4)—S(1)—C(5)—C(6) | −81.53 (9) | H(21)—C(25)—C(20)—C(19) | −0.0 (2) |
| C(4)—S(1)—C(5)—H(1) | 41.6 (1) | H(21)—C(25)—C(20)—C(21) | −179.9 (1) |
| C(4)—S(1)—C(5)—H(2) | 160.37 (9) | C(25)—C(24)—C(23)—C(22) | 1.5 (2) |
| C(4)—S(2)—C(12)—C(13) | −92.08 (6) | C(25)—C(24)—C(23)—H(19) | −178.9 (1) |
| C(4)—S(2)—C(12)—H(8) | 26.5 (1) | H(20)—C(24)—C(23)—C(22) | −177.4 (1) |
| C(4)—S(2)—C(12)—H(9) | 146.1 (1) | H(20)—C(24)—C(23)—H(19) | 2.2 (2) |
| C(12)—S(2)—C(4)—S(1) | −49.13 (5) | C(6)—C(7)—C(8)—C(9) | −0.4 (3) |
| C(12)—S(2)—C(4)—C(3) | 127.28 (7) | C(6)—C(7)—C(8)—H(4) | −179.5 (2) |
| C(19)—S(3)—C(2)—C(3) | 36.39 (9) | H(3)—C(7)—C(8)—C(9) | 179.8 (2) |
| C(19)—S(3)—C(2)—C(1) | −150.95 (9) | H(3)—C(7)—C(8)—H(4) | 0.7 (3) |
| C(2)—S(3)—C(19)—C(20) | −168.16 (7) | C(12)—C(13)—C(18)—C(17) | −176.9 (2) |
| C(2)—S(3)—C(19)—H(15) | −49.3 (2) | C(12)—C(13)—C(18)—H(14) | 3.9 (3) |
| C(2)—S(3)—C(19)—H(16) | 71.9 (1) | C(14)—C(13)—C(18)—C(17) | 1.1 (2) |
| C(2)—C(3)—N(1)—O(2) | 54.1 (1) | C(14)—C(13)—C(18)—H(14) | −178.1 (2) |
| C(2)—C(3)—N(1)—O(1) | −122.3 (1) | C(12)—C(13)—C(14)—C(15) | 177.4 (2) |
| C(4)—C(3)—N(1)—O(2) | −126.7 (1) | C(12)—C(13)—C(14)—H(10) | −3.4 (3) |
| C(4)—C(3)—N(1)—O(1) | 56.8 (1) | C(18)—C(13)—C(14)—C(15) | −0.5 (2) |
| N(1)—C(3)—C(2)—S(3) | 67.42 (9) | C(18)—C(13)—C(14)—H(10) | 178.7 (2) |
| N(1)—C(3)—C(2)—C(1) | −105.1 (1) | C(6)—C(11)—C(10)—C(9) | 1.0 (2) |
| C(4)—C(3)—C(2)—S(3) | −111.7 (1) | C(6)—C(11)—C(10)—H(6) | −179.3 (2) |
| C(4)—C(3)—C(2)—C(1) | 75.8 (1) | H(7)—C(11)—C(10)—C(9) | −178.8 (2) |
| N(1)—C(3)—C(4)—S(1) | 171.14 (6) | H(7)—C(11)—C(10)—H(6) | 1.0 (3) |
| N(1)—C(3)—C(4)—S(2) | −5.4 (1) | C(23)—C(22)—C(21)—C(20) | 0.7 (2) |
| C(2)—C(3)—C(4)—S(1) | −9.9 (1) | C(23)—C(22)—C(21)—H(17) | 179.3 (1) |
| C(2)—C(3)—C(4)—S(2) | 173.60 (7) | H(18)—C(22)—C(21)—C(20) | −179.4 (2) |
| C(7)—C(6)—C(5)—S(1) | 98.1 (1) | H(18)—C(22)—C(21)—H(17) | −0.8 (2) |
| C(7)—C(6)—C(5)—H(1) | −24.8 (2) | C(21)—C(22)—C(23)—C(24) | −1.6 (2) |
| C(7)—C(6)—C(5)—H(2) | −143.6 (1) | C(21)—C(22)—C(23)—H(19) | 178.8 (2) |
| C(11)—C(6)—C(5)—S(1) | −82.6 (1) | H(18)—C(22)—C(23)—C(24) | 178.5 (2) |
| C(11)—C(6)—C(5)—H(1) | 154.5 (2) | H(18)—C(22)—C(23)—H(19) | −1.1 (2) |
| C(11)—C(6)—C(5)—H(2) | 35.7 (2) | C(19)—C(20)—C(21)—C(22) | −179.5 (1) |
| C(5)—C(6)—C(7)—C(8) | −179.2 (1) | C(19)—C(20)—C(21)—H(17) | 1.9 (2) |
| C(5)—C(6)—C(7)—H(3) | 0.6 (2) | C(25)—C(20)—C(21)—C(22) | 0.3 (2) |
| C(11)—C(6)—C(7)—C(8) | 1.4 (2) | C(25)—C(20)—C(21)—H(17) | −178.3 (1) |
| C(11)—C(6)—C(7)—H(3) | −178.7 (2) | C(13)—C(18)—C(17)—C(16) | −1.1 (3) |
| C(5)—C(6)—C(11)—C(10) | 179.0 (1) | C(13)—C(18)—C(17)—H(13) | 179.0 (3) |
| C(5)—C(6)—C(11)—H(7) | −1.2 (2) | H(14)—C(18)—C(17)—C(16) | 178.1 (2) |
| C(7)—C(6)—C(11)—C(10) | −1.7 (2) | H(14)—C(18)—C(17)—H(13) | −1.8 (4) |
| C(7)—C(6)—C(11)—H(7) | 178.1 (2) | C(7)—C(8)—C(9)—C(10) | −0.3 (3) |
| S(3)—C(2)—C(1)—Cl(2) | −172.16 (8) | C(7)—C(8)—C(9)—H(5) | 178.3 (2) |
| S(3)—C(2)—C(1)—Cl(1) | 6.0 (2) | H(4)—C(8)—C(9)—C(10) | 178.8 (2) |
| C(3)—C(2)—C(1)—Cl(2) | 0.1 (2) | H(4)—C(8)—C(9)—H(5) | −2.6 (4) |
| C(3)—C(2)—C(1)—Cl(1) | 178.23 (9) | C(13)—C(14)—C(15)—C(16) | 0.1 (3) |
| S(2)—C(12)—C(13)—C(18) | 65.4 (1) | C(13)—C(14)—C(15)—H(11) | 179.3 (3) |
| S(2)—C(12)—C(13)—C(14) | −112.5 (1) | H(10)—C(14)—C(15)—C(16) | −179.1 (3) |
| H(8)—C(12)—C(13)—C(18) | −53.9 (2) | H(10)—C(14)—C(15)—H(11) | 0.1 (4) |
| H(8)—C(12)—C(13)—C(14) | 128.2 (2) | C(11)—C(10)—C(9)—C(8) | 0.1 (3) |
| H(9)—C(12)—C(13)—C(18) | −172.9 (2) | C(11)—C(10)—C(9)—H(5) | −178.6 (2) |
| H(9)—C(12)—C(13)—C(14) | 9.2 (2) | H(6)—C(10)—C(9)—C(8) | −179.7 (2) |
| S(3)—C(19)—C(20)—C(25) | −108.2 (1) | H(6)—C(10)—C(9)—H(5) | 1.6 (3) |
| S(3)—C(19)—C(20)—C(21) | 71.6 (1) | C(14)—C(15)—C(16)—C(17) | −0.1 (4) |
| H(15)—C(19)—C(20)—C(25) | 132.3 (1) | C(14)—C(15)—C(16)—H(12) | −178.4 (3) |
| H(15)—C(19)—C(20)—C(21) | −47.8 (2) | H(11)—C(15)—C(16)—C(17) | −179.4 (3) |
| H(16)—C(19)—C(20)—C(25) | 12.0 (2) | H(11)—C(15)—C(16)—H(12) | 2.3 (5) |
| H(16)—C(19)—C(20)—C(21) | −168.2 (1) | C(15)—C(16)—C(17)—C(18) | 0.7 (4) |
| C(20)—C(25)—C(24)—C(23) | −0.5 (2) | C(15)—C(16)—C(17)—H(13) | −179.5 (3) |
| C(20)—C(25)—C(24)—H(20) | 178.4 (1) | H(12)—C(16)—C(17)—C(18) | 179.0 (3) |
| H(21)—C(25)—C(24)—C(23) | 179.0 (1) | H(12)—C(16)—C(17)—H(13) | −1.2 (5) |
| H(21)—C(25)—C(24)—H(20) | −2.2 (2) |
| Symmetry codes: (i) −x+1, −y−1, −z; (ii) −x+1, −y, −z; (iii) x, y−1, z; (iv) −x, −y, −z; (v) x+1, y, z; (vi) x+1, y−1, z; (vii) x, y+1, z. |
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There are numerous publications devoted to the synthesis of halogenobutadienes containing atom of chlorine. They possess a broad spectrum of useful properties: they are employed as monomers for the preparation of valuable polymers and copolymers resistant to heat, light, chemical corrosion and so on. And they show algicidal, bactericidal fungicidal activities (Kalatskaya & Malama, 1986). A number of halogenobutadienes manifest high antitumour activity. However, there are a few reports on the crystal structures of nitrobutadiene compounds (Ibis et al., 2006a,b). It is the first publication about single-crystal structure of 1,1,3-tris(arylthio)nitrobutadiene derivative. The title compound was synthesized from 2-nitropentachlorobutadiene and benzyl mercaptan (Ibis & Aydinli, 1999). It is note that, our spectroscopic data are in accordance with reported by this article but apparently, title compound is not a 1,1,4-substituted, but a 1,1,3-substituted regioisomer instead. This indication was proven by X-ray analysis newly. Crystallographic analysis was carried out and the results are presented in this paper.
The molecular structure of the title compound is shown in Fig. 1. The three phenyl rings are inclined with the butadiene group at angles of 85.9 (1), 61.9 (1), 81.4 (1)°, respectively. The butadiene unit has assumed a configuration close to cisoid, but is not completely planar; torsion angle of C4—C3—C2—C1 is 75.3 (2)°.