PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o272.
Published online 2009 January 10. doi:  10.1107/S1600536808043419
PMCID: PMC2968351

2,4,4-Tris(benzyl­sulfan­yl)-1,1-dichloro-3-nitro­buta-1,3-diene

Abstract

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)°.

Related literature

The C—C bond lengths of the butadiene chain agree well with corresponding distances in a similar compound (Surange et al., 1997 [triangle]). For the biological activity of halogenobutadienes containing chlorine, see: Kalatskaya & Malama (1986 [triangle]). For the structures of nitro­butadienes, see: Ibis et al. (2006a [triangle],b [triangle]). For the synthesis, see: Ibis & Aydinli (1999 [triangle]). For weighting schemes, see: Carruthers & Watkin (1979 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o272-scheme1.jpg

Experimental

Crystal data

  • C25H21Cl2NO2S3
  • M r = 534.53
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o272-efi1.jpg
  • a = 10.1595 (10) Å
  • b = 11.5706 (10) Å
  • c = 12.5451 (2)
  • α = 74.887 (6)°
  • β = 69.259 (5)°
  • γ = 69.344 (5)°
  • V = 1274.83 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.52 mm−1
  • T = 293 K
  • 0.60 × 0.60 × 0.10 mm

Data collection

  • Rigaku R-AXIS diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.731, T max = 0.949
  • 101262 measured reflections
  • 7512 independent reflections
  • 7264 reflections with F 2 > 2.0σ(F 2)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.045
  • S = 1.20
  • 6957 reflections
  • 319 parameters
  • H atoms treated by a mixture of independent and constrained refinment
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: PROCESS (Rigaku, 1996 [triangle]); cell refinement: PROCESS; data reduction: CrystalStructure (Rigaku/MSC, 2003 [triangle]); program(s) used to solve structure: SIR92 (Altomare et al., 1994 [triangle]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2003 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043419/xu2466sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043419/xu2466Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Research Fund of the University of Istanbul.

supplementary crystallographic information

Comment

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)°.

Experimental

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).

Refinement

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).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C25H21Cl2NO2S3Z = 2
Mr = 534.53F(000) = 552.00
Triclinic, P1Dx = 1.392 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 10.1595 (10) ÅCell parameters from 10024 reflections
b = 11.5706 (10) Åθ = 2.2–30.5°
c = 12.5451 ŵ = 0.52 mm1
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

Data collection

Rigaku R-AXIS diffractometer7264 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.024
ω scansθmax = 30.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −14→14
Tmin = 0.731, Tmax = 0.949k = −16→16
101262 measured reflectionsl = −17→17
7512 independent reflections

Refinement

Refinement on FAll 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 = 1.20Δρmax = 0.31 e Å3
6957 reflectionsΔρmin = −0.34 e Å3
319 parameters

Special details

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).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/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)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
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)

Geometric parameters (Å, °)

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)ii3.029 (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)i3.542 (2)C(23)···H(10)ii3.085 (2)
S(1)···C(17)i3.562 (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)ii3.5522 (9)C(18)···H(8)i3.358 (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)ii3.202 (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)iv3.233 (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)ii2.963 (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)i3.552 (1)C(10)···C(7)2.735 (2)
Cl(2)···H(10)i3.526 (2)C(10)···C(8)2.368 (2)
Cl(2)···H(14)2.927 (1)C(10)···H(1)iv3.297 (2)
Cl(2)···H(18)iii3.565 (1)C(10)···H(2)iv3.564 (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)iii3.210 (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)iv3.485 (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)ii3.128 (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)i3.542 (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)i3.121 (2)
N(1)···C(1)3.375 (1)C(16)···H(4)ii3.549 (2)
N(1)···H(3)ii3.541 (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)iv3.587 (2)C(17)···S(1)i3.562 (3)
C(6)···C(4)3.482 (1)C(17)···C(13)2.398 (2)
C(6)···C(5)iv3.584 (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)i3.118 (2)
C(6)···C(9)2.762 (2)C(17)···H(4)vi3.485 (3)
C(6)···H(1)2.023 (1)C(17)···H(11)3.194 (3)
C(6)···H(1)iv3.463 (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)iv3.167 (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)iv3.463 (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)ii3.558 (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)iv3.131 (2)
C(2)···N(1)2.439 (1)H(1)···C(10)iv3.297 (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)iv3.167 (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)iv3.056 (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)iv3.398 (2)
C(12)···C(4)2.794 (1)H(2)···C(8)iv3.233 (3)
C(12)···C(18)2.490 (2)H(2)···C(10)iv3.564 (2)
C(12)···C(14)2.503 (2)H(2)···C(9)iv3.485 (2)
C(12)···H(1)3.013 (1)H(2)···C(16)i3.121 (2)
C(12)···H(10)2.675 (2)H(2)···C(17)i3.118 (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)ii3.202 (2)
C(4)···O(2)3.363 (2)H(3)···N(1)ii3.541 (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)ii2.685 (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)ii3.260 (2)
C(4)···H(1)2.822 (2)H(4)···C(14)ii2.963 (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)ii3.128 (3)
C(4)···H(14)2.859 (1)H(4)···C(16)ii3.549 (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)ii3.5522 (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)ii3.540 (1)H(7)···C(6)2.022 (2)
O(1)···H(1)ii3.558 (2)H(7)···C(5)2.656 (2)
O(1)···H(3)ii2.685 (1)H(7)···C(7)3.221 (2)
O(1)···H(7)v3.125 (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)iv3.584 (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)i3.358 (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)i3.552 (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)ii3.232 (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)i3.526 (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)ii3.060 (2)
C(19)···H(17)2.698 (2)H(10)···C(24)ii3.077 (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)ii3.042 (2)
C(25)···C(22)2.731 (2)H(10)···C(20)ii3.057 (2)
C(25)···C(21)2.366 (2)H(10)···C(21)ii3.029 (2)
C(25)···C(23)2.374 (2)H(10)···C(23)ii3.085 (2)
C(25)···H(10)ii3.060 (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)vi2.911 (2)
C(24)···C(21)2.738 (1)H(13)···C(9)vi2.995 (2)
C(24)···H(10)ii3.077 (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)ii3.540 (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)iv3.056 (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)ii3.260 (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)iv3.131 (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)iv3.398 (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)vii3.565 (1)
C(22)···H(10)ii3.042 (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)vii3.210 (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)ii3.057 (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)ii3.232 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2466).

References

  • Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.27, 435.
  • Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst.36, 1487.
  • Carruthers, J. R. & Watkin, D. J. (1979). Acta Cryst. A35, 698–699.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Ibis, C. & Aydinli, G. (1999). Sulfur Lett.23, 67–77.
  • Ibis, C., Sayil, M. C. & Deniz, N. G. (2006a). Acta Cryst. E62, o800–o801.
  • Ibis, C., Sayil, M. C. & Ozkok, F. (2006b). Acta Cryst. E62, o1147–o1148.
  • Kalatskaya, L. M. & Malama, A. A. (1986). Mikrobiologiya, 55, 618–621.
  • Rigaku (1996). PROCESS Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2003). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Surange, S. S., Kumaran, G., Rajappa, S., Rajalakshmi, K. & Pattabhi, V. (1997). Tetrahedron, 53, 8531–8540.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography