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The title compound, C18H14Cl3NO2S2, was synthesized by the reaction of 1,1,2,4-tetra­chloro-4-(4-methyl­phenyl­sulfan­yl)-3-nitro­buta-1,3-diene with ethanedithiol. The butadiene unit is not completely planar as would be expected if the two double bonds were fully conjugated The torsion angle of the butadiene unit is -82.2 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050957/im2039sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050957/im2039Isup2.hkl
Contains datablock I

CCDC reference: 669141

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.036
  • wR factor = 0.049
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The chemistry of compounds exhibiting nitro and additional halogen substituents, has been intensively studied in recent decades. These highly reactive substances have been used to develop preparative methods for the synthesis of complex polyfunctional derivatives of different classes. The synthesis of unsaturated thio-substituted halogenated organic compounds from the reaction of various halogenated alkenes and dienes with a number of thiols were published (Ibis & Deniz, 2007a). The aim in this study was to determine the conformation of 1,1,2-trichloro-4,4-bis(4'-methylphenylsulfanyl)-3-nitro-buta-1,3-diene (Ibis, 1996). The butadiene unit is not completely planar as it would be expected if the two double bonds were fully conjugated. The torsional angle of the butadiene unit (C1—C2—C3—C4) is -82.2 (5)°. The C—C bond lengths of the butadiene chain agree well with corresponding distances in a similar compound. (Ibis & Deniz, 2006, 2007b). Both phenyl rings are planar with maximum deviations of 0.0087 (1) Å and 0.0101 (1) Å and are inclined at an angle of 15.1 (1)°.

Related literature top

For related literature, see: Ibis (1996); Ibis & Deniz (2006, 2007a,b); Carruthers & Watkin (1979).

Experimental top

A mixture of 1,1,2,4-tetrachloro-4-(4-methylphenylsulfanyl)-3-nitro- buta-1,3-diene (1.98 g, 5.52 mmol) and ethanedithiol (0.52 g, 5.52 mmol) was stirred in ethanol (35 ml) and 2 g sodium hydroxide in 10 ml water was added at room temperature. The mixture was stirred for another 2 h. Chloroform (50 ml) was added to the reaction mixture. The organic layer was separated and washed with water (4x30 ml), and dried with MgSO4. The solvent was evaporated and the residue was purified by column chromatography on silica gel (0.063–0.20 mm; E. Merck). The title compound was obtained as a side product next to the main product 2-(4-methylphenylsulfanyl)-3-nitro-4,5-dichloro-1,6-dithia-octane-2,4-diene during this reaction sequence (Ibis et al., 1996). Yellow crystals of (I) suitable for X-ray diffraction analysis were obtained by slow evaporation of an ethanolic solution at room temperature (yield: 0.19 g, 8%; m.p. 392–393 K).

Refinement top

The non-hydrogen atoms were refined anisotropically. H atoms were located in geometrically idealized positions C—H = 0.95 (6) Å and treated as riding and Uiso(H) = 1.2Ueq(C).

Structure description top

The chemistry of compounds exhibiting nitro and additional halogen substituents, has been intensively studied in recent decades. These highly reactive substances have been used to develop preparative methods for the synthesis of complex polyfunctional derivatives of different classes. The synthesis of unsaturated thio-substituted halogenated organic compounds from the reaction of various halogenated alkenes and dienes with a number of thiols were published (Ibis & Deniz, 2007a). The aim in this study was to determine the conformation of 1,1,2-trichloro-4,4-bis(4'-methylphenylsulfanyl)-3-nitro-buta-1,3-diene (Ibis, 1996). The butadiene unit is not completely planar as it would be expected if the two double bonds were fully conjugated. The torsional angle of the butadiene unit (C1—C2—C3—C4) is -82.2 (5)°. The C—C bond lengths of the butadiene chain agree well with corresponding distances in a similar compound. (Ibis & Deniz, 2006, 2007b). Both phenyl rings are planar with maximum deviations of 0.0087 (1) Å and 0.0101 (1) Å and are inclined at an angle of 15.1 (1)°.

For related literature, see: Ibis (1996); Ibis & Deniz (2006, 2007a,b); Carruthers & Watkin (1979).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); 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.
1,1,2-Trichloro-4,4-bis(4-methylphenylsulfanyl)-3-nitrobuta-1,3-diene top
Crystal data top
C18H14Cl3NO2S2F(000) = 912.00
Mr = 446.79Dx = 1.486 Mg m3
Monoclinic, P21/nMelting point = 392–393 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.7107 Å
a = 13.885 (1) ÅCell parameters from 5659 reflections
b = 6.8246 (6) Åθ = 2.9–25.3°
c = 21.313 (2) ŵ = 0.68 mm1
β = 98.630 (5)°T = 294 K
V = 1996.7 (3) Å3Needle, yellow
Z = 40.40 × 0.20 × 0.10 mm
Data collection top
Rigaku R-AXIS RAPID S
diffractometer
3254 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.086
ω scansθmax = 25.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1616
Tmin = 0.849, Tmax = 0.935k = 87
69322 measured reflectionsl = 2525
3653 independent reflections
Refinement top
Refinement on F0 restraints
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.049 Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 14.9656 -4.4915 13.6461
S = 1.12(Δ/σ)max = 0.026
3254 reflectionsΔρmax = 0.38 e Å3
235 parametersΔρmin = 0.25 e Å3
Crystal data top
C18H14Cl3NO2S2V = 1996.7 (3) Å3
Mr = 446.79Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.885 (1) ŵ = 0.68 mm1
b = 6.8246 (6) ÅT = 294 K
c = 21.313 (2) Å0.40 × 0.20 × 0.10 mm
β = 98.630 (5)°
Data collection top
Rigaku R-AXIS RAPID S
diffractometer
3653 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
3254 reflections with F2 > 2σ(F2)
Tmin = 0.849, Tmax = 0.935Rint = 0.086
69322 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.049H-atom parameters constrained
S = 1.12Δρmax = 0.38 e Å3
3254 reflectionsΔρmin = 0.25 e Å3
235 parameters
Special details top

Geometry. Least Squares Planes

————– Plane number 1 —————

Atoms Defining Plane Distance e.s.d. C1 [1;0;0;0] -0.1397 0.0013 C2 [1;0;0;0] 0.3219 0.0029 C3 [1;0;0;0] -0.2390 0.0022 C4 [1;0;0;0] 0.0847 0.0008

Additional Atoms Distance e.s.d.

Mean deviation from plane is 0.1963 angstrom Chi-squared: 12552.825

————– Plane number 2 —————

Atoms Defining Plane Distance e.s.d. C5 [1;0;0;0] 0.0121 0.0028 C6 [1;0;0;0] -0.0118 0.0029 C7 [1;0;0;0] -0.0009 0.0031 C8 [1;0;0;0] 0.0136 0.0030 C9 [1;0;0;0] -0.0135 0.0031 C10 [1;0;0;0] -0.0004 0.0027

Additional Atoms Distance e.s.d.

Mean deviation from plane is 0.0087 angstrom Chi-squared: 37.790

————– Plane number 3 —————

Atoms Defining Plane Distance e.s.d. C12 [1;0;0;0] -0.0141 0.0030 C13 [1;0;0;0] 0.0049 0.0031 C14 [1;0;0;0] 0.0115 0.0037 C15 [1;0;0;0] -0.0165 0.0038 C16 [1;0;0;0] 0.0021 0.0034 C17 [1;0;0;0] 0.0116 0.0031

Additional Atoms Distance e.s.d.

Mean deviation from plane is 0.0101 angstrom Chi-squared: 33.959

Dihedral angles between least-squares planes ——————————————–

plane plane angle e.s.d. 1 2 142.942 0.132 1 3 152.025 0.166 2 3 15.008 0.151

Refinement. Refinement using reflections with F2 > 3.0 σ(F2). 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 σ(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)0.56841 (7)0.0359 (2)0.88785 (4)0.0565 (3)
Cl(1)0.34904 (7)0.2935 (2)0.74876 (5)0.0720 (3)
Cl(2)0.55665 (8)0.3657 (2)0.76900 (5)0.0700 (3)
S(2)0.74902 (7)0.2064 (2)0.83810 (4)0.0595 (3)
Cl(3)0.38832 (8)0.1596 (2)0.74025 (7)0.0830 (4)
O(1)0.5776 (2)0.0536 (5)0.65928 (12)0.0732 (9)
O(2)0.6947 (2)0.2191 (5)0.71320 (13)0.0775 (10)
N(1)0.6211 (2)0.1190 (5)0.7097 (1)0.0564 (10)
C(10)0.6222 (3)0.1431 (6)1.0105 (2)0.0556 (11)
C(5)0.6007 (3)0.2113 (6)0.9486 (2)0.0502 (10)
C(3)0.5809 (3)0.0756 (5)0.7665 (2)0.0487 (10)
C(2)0.4828 (2)0.0080 (6)0.7558 (2)0.0508 (10)
C(7)0.6249 (3)0.5388 (6)0.9868 (2)0.0621 (12)
C(4)0.6323 (2)0.1088 (5)0.8259 (2)0.0473 (10)
C(6)0.6005 (3)0.4103 (6)0.9371 (2)0.0590 (11)
C(12)0.7987 (3)0.1309 (6)0.9161 (2)0.0539 (11)
C(13)0.8408 (3)0.2735 (7)0.9576 (2)0.0615 (12)
C(14)0.8875 (3)0.2180 (8)1.0170 (2)0.0682 (13)
C(8)0.6484 (3)0.4734 (6)1.0485 (2)0.0594 (12)
C(1)0.4645 (3)0.1987 (6)0.7574 (2)0.0526 (11)
C(15)0.8917 (3)0.0225 (8)1.0359 (2)0.0663 (13)
C(16)0.8512 (3)0.1173 (7)0.9926 (2)0.0677 (13)
C(9)0.6447 (3)0.2746 (6)1.0595 (2)0.0604 (12)
C(17)0.8053 (3)0.0643 (7)0.9327 (2)0.0602 (12)
C(11)0.6771 (4)0.6177 (8)1.1021 (2)0.082
C(18)0.9416 (4)0.0351 (9)1.1015 (2)0.091
H(1)0.5825 (3)0.4578 (6)0.8951 (2)0.071*
H(2)0.6258 (3)0.6758 (6)0.9791 (2)0.075*
H(3)0.6583 (3)0.2279 (6)1.1018 (2)0.073*
H(4)0.6200 (3)0.0062 (6)1.0182 (2)0.068*
H(5)0.6919 (4)0.5500 (8)1.1413 (2)0.099*
H(6)0.7323 (4)0.6911 (8)1.0944 (2)0.099*
H(7)0.6239 (4)0.7038 (8)1.1038 (2)0.099*
H(8)0.8383 (3)0.4066 (7)0.9444 (2)0.074*
H(9)0.9154 (3)0.3151 (8)1.0461 (2)0.082*
H(10)0.8549 (3)0.2514 (7)1.0047 (2)0.082*
H(11)0.7786 (3)0.1610 (7)0.9030 (2)0.072*
H(12)0.9391 (4)0.1731 (9)1.1068 (2)0.109*
H(13)1.0077 (4)0.0061 (9)1.1063 (2)0.109*
H(14)0.9099 (4)0.0275 (9)1.1326 (2)0.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S(1)0.0593 (5)0.0684 (7)0.0447 (5)0.0163 (5)0.0170 (4)0.0056 (4)
Cl(1)0.0565 (6)0.0882 (8)0.0716 (6)0.0201 (5)0.0110 (5)0.0034 (6)
Cl(2)0.0672 (6)0.0618 (7)0.0794 (7)0.0068 (5)0.0056 (5)0.0047 (5)
S(2)0.0539 (5)0.0762 (7)0.0493 (5)0.0174 (5)0.0112 (4)0.0020 (5)
Cl(3)0.0571 (6)0.0748 (8)0.1148 (9)0.0163 (5)0.0057 (6)0.0009 (6)
O(1)0.075 (2)0.100 (2)0.045 (1)0.002 (2)0.0105 (12)0.007 (2)
O(2)0.079 (2)0.100 (2)0.057 (2)0.026 (2)0.021 (1)0.011 (2)
N(1)0.056 (2)0.073 (2)0.042 (2)0.002 (2)0.011 (1)0.005 (1)
C(10)0.071 (2)0.053 (2)0.046 (2)0.001 (2)0.015 (2)0.003 (2)
C(5)0.053 (2)0.059 (2)0.040 (2)0.000 (2)0.013 (1)0.001 (2)
C(3)0.051 (2)0.052 (2)0.045 (2)0.000 (2)0.014 (2)0.001 (2)
C(2)0.047 (2)0.063 (3)0.043 (2)0.002 (2)0.010 (1)0.005 (2)
C(7)0.072 (2)0.056 (2)0.059 (2)0.004 (2)0.011 (2)0.001 (2)
C(4)0.048 (2)0.052 (2)0.044 (2)0.003 (2)0.013 (1)0.000 (2)
C(6)0.070 (2)0.066 (3)0.040 (2)0.005 (2)0.006 (2)0.006 (2)
C(12)0.046 (2)0.070 (3)0.048 (2)0.004 (2)0.012 (2)0.001 (2)
C(13)0.052 (2)0.072 (3)0.059 (2)0.008 (2)0.007 (2)0.008 (2)
C(14)0.058 (2)0.091 (4)0.055 (2)0.005 (2)0.007 (2)0.022 (2)
C(8)0.065 (2)0.070 (3)0.045 (2)0.002 (2)0.010 (2)0.005 (2)
C(1)0.050 (2)0.065 (3)0.042 (2)0.008 (2)0.007 (1)0.003 (2)
C(15)0.050 (2)0.095 (4)0.055 (2)0.008 (2)0.013 (2)0.004 (2)
C(16)0.070 (3)0.074 (3)0.062 (2)0.011 (2)0.018 (2)0.005 (2)
C(9)0.073 (3)0.065 (3)0.043 (2)0.003 (2)0.010 (2)0.004 (2)
C(17)0.060 (2)0.070 (3)0.051 (2)0.000 (2)0.010 (2)0.012 (2)
C(11)0.102 (4)0.077 (3)0.066 (3)0.007 (3)0.015 (2)0.013 (2)
C(18)0.079 (3)0.131 (5)0.062 (3)0.008 (3)0.004 (2)0.003 (3)
Geometric parameters (Å, º) top
S(1)—C(5)1.771 (4)C(12)—C(13)1.384 (6)
S(1)—C(4)1.768 (4)C(12)—C(17)1.377 (6)
Cl(1)—C(1)1.713 (4)C(13)—C(14)1.386 (5)
Cl(2)—C(1)1.703 (4)C(13)—H(8)0.950 (6)
S(2)—C(4)1.736 (3)C(14)—C(15)1.392 (7)
S(2)—C(12)1.779 (4)C(14)—H(9)0.950 (6)
Cl(3)—C(2)1.734 (4)C(8)—C(9)1.379 (6)
O(1)—N(1)1.235 (4)C(8)—C(11)1.516 (6)
O(2)—N(1)1.221 (5)C(15)—C(16)1.387 (6)
N(1)—C(3)1.437 (5)C(15)—C(18)1.517 (6)
C(10)—C(5)1.387 (5)C(16)—C(17)1.387 (5)
C(10)—C(9)1.377 (5)C(16)—H(10)0.950 (7)
C(10)—H(4)0.950 (6)C(9)—H(3)0.950 (5)
C(5)—C(6)1.380 (6)C(17)—H(11)0.950 (6)
C(3)—C(2)1.462 (5)C(11)—H(5)0.950 (7)
C(3)—C(4)1.377 (5)C(11)—H(6)0.950 (8)
C(2)—C(1)1.328 (6)C(11)—H(7)0.950 (8)
C(7)—C(6)1.379 (5)C(18)—H(12)0.950 (9)
C(7)—C(8)1.379 (5)C(18)—H(13)0.950 (7)
C(7)—H(2)0.950 (6)C(18)—H(14)0.950 (7)
C(6)—H(1)0.950 (5)
C(5)—S(1)—C(4)104.8 (2)C(15)—C(14)—C(13)121.3 (4)
C(4)—S(2)—C(12)104.6 (2)H(9)—C(14)—C(13)119.7 (6)
C(3)—N(1)—O(1)117.2 (3)C(9)—C(8)—C(11)121.6 (3)
C(3)—N(1)—O(2)119.4 (3)C(9)—C(8)—C(7)118.1 (3)
O(1)—N(1)—O(2)123.4 (3)C(11)—C(8)—C(7)120.4 (4)
C(5)—C(10)—C(9)119.6 (4)Cl(1)—C(1)—Cl(2)115.7 (2)
C(5)—C(10)—H(4)119.2 (4)Cl(1)—C(1)—C(2)123.2 (3)
C(9)—C(10)—H(4)121.2 (4)Cl(2)—C(1)—C(2)121.1 (3)
C(6)—C(5)—S(1)122.7 (3)C(16)—C(15)—C(18)121.3 (5)
C(6)—C(5)—C(10)119.6 (3)C(16)—C(15)—C(14)118.2 (4)
S(1)—C(5)—C(10)117.6 (3)C(18)—C(15)—C(14)120.6 (4)
C(2)—C(3)—C(4)123.3 (3)C(17)—C(16)—H(10)119.9 (5)
C(2)—C(3)—N(1)114.8 (3)C(17)—C(16)—C(15)121.2 (4)
C(4)—C(3)—N(1)121.8 (3)H(10)—C(16)—C(15)118.9 (5)
C(1)—C(2)—Cl(3)120.6 (3)H(3)—C(9)—C(10)119.5 (5)
C(1)—C(2)—C(3)123.8 (3)H(3)—C(9)—C(8)119.0 (5)
Cl(3)—C(2)—C(3)115.6 (3)C(10)—C(9)—C(8)121.5 (3)
C(6)—C(7)—C(8)121.5 (4)H(11)—C(17)—C(12)119.8 (4)
C(6)—C(7)—H(2)120.1 (4)H(11)—C(17)—C(16)120.8 (5)
C(8)—C(7)—H(2)118.4 (4)C(12)—C(17)—C(16)119.5 (4)
S(1)—C(4)—S(2)123.9 (2)H(5)—C(11)—H(6)109.5 (6)
S(1)—C(4)—C(3)113.1 (3)H(5)—C(11)—H(7)109.5 (7)
S(2)—C(4)—C(3)123.0 (3)H(5)—C(11)—C(8)110.2 (5)
H(1)—C(6)—C(5)119.8 (4)H(6)—C(11)—H(7)109.5 (7)
H(1)—C(6)—C(7)120.5 (5)H(6)—C(11)—C(8)109.9 (5)
C(5)—C(6)—C(7)119.7 (3)H(7)—C(11)—C(8)108.3 (5)
C(13)—C(12)—C(17)120.7 (3)H(12)—C(18)—H(13)109.5 (7)
C(13)—C(12)—S(2)117.5 (3)H(12)—C(18)—H(14)109.5 (7)
C(17)—C(12)—S(2)121.4 (3)H(12)—C(18)—C(15)110.3 (5)
C(14)—C(13)—H(8)121.5 (5)H(13)—C(18)—H(14)109.5 (7)
C(14)—C(13)—C(12)119.1 (4)H(13)—C(18)—C(15)108.8 (5)
H(8)—C(13)—C(12)119.4 (4)H(14)—C(18)—C(15)109.3 (5)
C(15)—C(14)—H(9)119.0 (5)
C(4)—S(1)—C(5)—C(10)136.8 (3)H(2)—C(7)—C(8)—C(9)178.5 (5)
C(4)—S(1)—C(5)—C(6)46.5 (3)H(2)—C(7)—C(8)—C(11)1.4 (7)
C(5)—S(1)—C(4)—S(2)37.1 (3)S(2)—C(12)—C(13)—C(14)174.7 (3)
C(5)—S(1)—C(4)—C(3)144.4 (3)S(2)—C(12)—C(13)—H(8)4.0 (6)
C(12)—S(2)—C(4)—S(1)20.6 (3)C(17)—C(12)—C(13)—C(14)1.8 (6)
C(12)—S(2)—C(4)—C(3)157.7 (3)C(17)—C(12)—C(13)—H(8)176.8 (5)
C(4)—S(2)—C(12)—C(13)129.4 (3)S(2)—C(12)—C(17)—C(16)175.2 (3)
C(4)—S(2)—C(12)—C(17)57.9 (3)S(2)—C(12)—C(17)—H(11)4.6 (6)
O(1)—N(1)—C(3)—C(2)11.5 (5)C(13)—C(12)—C(17)—C(16)2.6 (6)
O(1)—N(1)—C(3)—C(4)167.6 (4)C(13)—C(12)—C(17)—H(11)177.2 (5)
O(2)—N(1)—C(3)—C(2)167.5 (3)C(12)—C(13)—C(14)—C(15)0.8 (6)
O(2)—N(1)—C(3)—C(4)13.4 (6)C(12)—C(13)—C(14)—H(9)178.8 (5)
C(9)—C(10)—C(5)—S(1)178.0 (3)H(8)—C(13)—C(14)—C(15)179.4 (5)
C(9)—C(10)—C(5)—C(6)1.1 (6)H(8)—C(13)—C(14)—H(9)2.6 (8)
H(4)—C(10)—C(5)—S(1)0.9 (6)C(13)—C(14)—C(15)—C(16)2.5 (6)
H(4)—C(10)—C(5)—C(6)177.8 (5)C(13)—C(14)—C(15)—C(18)179.0 (4)
C(5)—C(10)—C(9)—C(8)1.4 (6)H(9)—C(14)—C(15)—C(16)179.5 (5)
C(5)—C(10)—C(9)—H(3)178.8 (5)H(9)—C(14)—C(15)—C(18)1.0 (7)
H(4)—C(10)—C(9)—C(8)179.7 (5)C(7)—C(8)—C(9)—C(10)2.6 (6)
H(4)—C(10)—C(9)—H(3)0.0 (8)C(7)—C(8)—C(9)—H(3)177.6 (5)
S(1)—C(5)—C(6)—C(7)178.9 (3)C(11)—C(8)—C(9)—C(10)177.5 (4)
S(1)—C(5)—C(6)—H(1)0.1 (7)C(11)—C(8)—C(9)—H(3)2.3 (7)
C(10)—C(5)—C(6)—C(7)2.2 (6)C(7)—C(8)—C(11)—H(5)179.2 (6)
C(10)—C(5)—C(6)—H(1)176.8 (5)C(7)—C(8)—C(11)—H(6)58.4 (7)
N(1)—C(3)—C(2)—Cl(3)83.0 (4)C(7)—C(8)—C(11)—H(7)61.1 (7)
N(1)—C(3)—C(2)—C(1)96.9 (4)C(9)—C(8)—C(11)—H(5)1.0 (8)
C(4)—C(3)—C(2)—Cl(3)97.8 (4)C(9)—C(8)—C(11)—H(6)121.7 (6)
C(4)—C(3)—C(2)—C(1)82.2 (5)C(9)—C(8)—C(11)—H(7)118.8 (6)
N(1)—C(3)—C(4)—S(1)178.0 (3)C(14)—C(15)—C(16)—C(17)1.7 (6)
N(1)—C(3)—C(4)—S(2)0.4 (5)C(14)—C(15)—C(16)—H(10)178.7 (5)
C(2)—C(3)—C(4)—S(1)1.1 (5)C(18)—C(15)—C(16)—C(17)179.8 (4)
C(2)—C(3)—C(4)—S(2)179.5 (3)C(18)—C(15)—C(16)—H(10)0.2 (7)
Cl(3)—C(2)—C(1)—Cl(1)3.4 (4)C(14)—C(15)—C(18)—H(12)179.2 (5)
Cl(3)—C(2)—C(1)—Cl(2)177.0 (2)C(14)—C(15)—C(18)—H(13)59.1 (7)
C(3)—C(2)—C(1)—Cl(1)176.6 (3)C(14)—C(15)—C(18)—H(14)60.4 (7)
C(3)—C(2)—C(1)—Cl(2)3.0 (5)C(16)—C(15)—C(18)—H(12)0.8 (7)
C(8)—C(7)—C(6)—C(5)1.0 (6)C(16)—C(15)—C(18)—H(13)119.4 (7)
C(8)—C(7)—C(6)—H(1)178.0 (5)C(16)—C(15)—C(18)—H(14)121.2 (6)
H(2)—C(7)—C(6)—C(5)179.1 (5)C(15)—C(16)—C(17)—C(12)0.8 (6)
H(2)—C(7)—C(6)—H(1)1.9 (8)C(15)—C(16)—C(17)—H(11)179.0 (5)
C(6)—C(7)—C(8)—C(9)1.4 (6)H(10)—C(16)—C(17)—C(12)178.8 (5)
C(6)—C(7)—C(8)—C(11)178.7 (4)H(10)—C(16)—C(17)—H(11)1.5 (8)

Experimental details

Crystal data
Chemical formulaC18H14Cl3NO2S2
Mr446.79
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)13.885 (1), 6.8246 (6), 21.313 (2)
β (°) 98.630 (5)
V3)1996.7 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.68
Crystal size (mm)0.40 × 0.20 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID S
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.849, 0.935
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
69322, 3653, 3254
Rint0.086
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.049, 1.12
No. of reflections3254
No. of parameters235
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.25

Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalStructure (Rigaku/MSC, 2003), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), ORTEP-3 (Farrugia, 1997).

 

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