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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 2| February 2009| Page o272
doi:10.1107/S1600536808043419

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

Goksin Aydinli,a* Cigdem Sayila and Cemil Ibisa

aIstanbul University, Faculty of Engineering, Department of Chemistry, 34320 Avcilar-Istanbul, Turkey
*Correspondence e-mail: goksayd@istanbul.edu.tr

(Received 25 November 2008; accepted 19 December 2008; online 10 January 2009)

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[Surange, S. S., Kumaran, G., Rajappa, S., Rajalakshmi, K. & Pattabhi, V. (1997). Tetrahedron, 53, 8531-8540.]). For the biological activity of halogenobutadienes containing chlorine, see: Kalatskaya & Malama (1986[Kalatskaya, L. M. & Malama, A. A. (1986). Mikrobiologiya, 55, 618-621.]). For the structures of nitro­butadienes, see: Ibis et al. (2006a[Ibis, C., Sayil, M. C. & Deniz, N. G. (2006a). Acta Cryst. E62, o800-o801.],b[Ibis, C., Sayil, M. C. & Ozkok, F. (2006b). Acta Cryst. E62, o1147-o1148.]). For the synthesis, see: Ibis & Aydinli (1999[Ibis, C. & Aydinli, G. (1999). Sulfur Lett. 23, 67-77.]). For weighting schemes, see: Carruthers & Watkin (1979[Carruthers, J. R. & Watkin, D. J. (1979). Acta Cryst. A35, 698-699.]).

[Scheme 1]

Experimental

Crystal data

  • C25H21Cl2NO2S3

  • Mr = 534.53

  • Triclinic, [P \overline 1]

  • 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.731, Tmax = 0.949

  • 101262 measured reflections

  • 7512 independent reflections

  • 7264 reflections with F2 > 2.0σ(F2)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 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[Rigaku (1996). PROCESS. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS; data reduction: CrystalStructure (Rigaku/MSC, 2003[Rigaku/MSC (2003). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2003[Rigaku/MSC (2003). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]).

Supporting information

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

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

checkCIF report


Comment top

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)°.

Related literature top

The C—C bond lengths of the butadiene chain agree well with corresponding distances in a similar compound (Surange et al., 1997). For the biological activity of halogenobutadienes

containing chlorine, see: Kalatskaya & Malama (1986). For the structures of nitrobutadienes, see: Ibis et al. (2006a,b). For the synthesis, see: Ibis & Aydinli (1999). For related literature, see: Carruthers & Watkin (1979).

Experimental top

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 top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
(I) top
Crystal data top
C25H21Cl2NO2S3Z = 2
Mr = 534.53F(000) = 552.00
Triclinic, P1Dx = 1.392 Mg m−3
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 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
Data collection top
Rigaku R-AXIS
diffractometer		7264 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 top
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 Å−3
6957 reflectionsΔρmin = −0.34 e Å−3
319 parameters
Crystal data top
C25H21Cl2NO2S3γ = 69.344 (5)°
Mr = 534.53V = 1274.83 (2) Å3
Triclinic, P1Z = 2
a = 10.1595 (10) ÅMo Kα radiation
b = 11.5706 (10) ŵ = 0.52 mm−1
c = 12.5451 ÅT = 293 K
α = 74.887 (6)°0.60 × 0.60 × 0.10 mm
β = 69.259 (5)°
Data collection top
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 = 0.949Rint = 0.024
101262 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066319 parameters
wR(F2) = 0.045All H-atom parameters refined
S = 1.20Δρmax = 0.31 e Å−3
6957 reflectionsΔρmin = −0.34 e Å−3
Special details top

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) top
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) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC25H21Cl2NO2S3
Mr534.53
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)10.1595 (10), 11.5706 (10), 12.5451
α, β, γ (°)74.887 (6), 69.259 (5), 69.344 (5)
V (Å3)1274.83 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.52
Crystal size (mm)0.60 × 0.60 × 0.10
Data collection
DiffractometerRigaku R-AXIS
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.731, 0.949
No. of measured, independent and
observed [F2 > 2.0σ(F2)] reflections		101262, 7512, 7264
Rint0.024
(sin θ/λ)max (Å−1)0.709
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.045, 1.20
No. of reflections6957
No. of parameters319
No. of restraints?
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.31, −0.34

Computer programs: PROCESS (Rigaku, 1996), CrystalStructure (Rigaku/MSC, 2003), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), ORTEP-3 (Farrugia, 1997).

 

Acknowledgements

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

References

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 First citationBetteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  Web of Science CrossRef IUCr Journals Google Scholar
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ISSN: 2056-9890
Volume 65| Part 2| February 2009| Page o272
doi:10.1107/S1600536808043419
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