1,3,4,4-Tetra­chloro-4-(4-chloro­phenyl­sulfan­yl)-2-nitro­buta-1,3-diene

Ibis, C.; Sayil, M.C.; Deniz, N.G.

doi:10.1107/S1600536806001838

1,3,4,4-Tetrachloro-4-(4-chlorophenylsulfanyl)-2-nitrobuta-1,3-diene

The molecule of the title compound, C₁₀H₄Cl₅NO₂S, is not planar. The chlorophenyl ring and the butadiene group are inclined at an angle of 59.5 (1)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001838/cf6485sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001838/cf6485Isup2.hkl Contains datablock I

CCDC reference: 298674

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.006 Å
R factor = 0.079
wR factor = 0.085
Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT704_ALERT_1_A Contact Calc    3.479(6), Rep    3.311(6), Dev..      28.00 Sigma
              C4   -C6      1.555   1.555

Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    Cl2    -   C1      ..      11.54 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    Cl3    -   C2      ..      15.91 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    Cl1    -   C1      ..       5.76 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT754_ALERT_4_C Contact Calc     3.14000, Rep    3.137(4) ......  Senseless su
              CL2  -H1      1.555   1.455
PLAT754_ALERT_4_C Contact Calc     3.52000, Rep    3.515(3) ......  Senseless su
              CL4  -H4      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.81000, Rep    2.809(4) ......  Senseless su
              S1   -H1      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.84000, Rep    2.835(4) ......  Senseless su
              S1   -H4      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.43000, Rep    3.431(5) ......  Senseless su
              C4   -H4      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.02000, Rep    2.020(6) ......  Senseless su
              C5   -H1      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.26000, Rep    3.263(6) ......  Senseless su
              C5   -H2      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.26000, Rep    3.261(6) ......  Senseless su
              C5   -H3      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.03000, Rep    2.035(6) ......  Senseless su
              C5   -H4      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.25000, Rep    3.254(6) ......  Senseless su
              C6   -H1      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.57000, Rep    3.566(7) ......  Senseless su
              C6   -H2      1.555   1.455
PLAT754_ALERT_4_C Contact Calc     2.05000, Rep    2.045(6) ......  Senseless su
              C6   -H3      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.26000, Rep    3.262(6) ......  Senseless su
              C7   -H2      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.04000, Rep    2.043(6) ......  Senseless su
              C7   -H4      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.23000, Rep    3.232(6) ......  Senseless su
              C8   -H1      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.03000, Rep    2.026(6) ......  Senseless su
              C8   -H2      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.03000, Rep    2.026(6) ......  Senseless su
              C8   -H3      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.25000, Rep    3.247(6) ......  Senseless su
              C8   -H4      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.04000, Rep    2.037(7) ......  Senseless su
              C9   -H1      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.26000, Rep    3.259(6) ......  Senseless su
              C9   -H3      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.58000, Rep    3.582(6) ......  Senseless su
              C9   -H3      1.555   2.665
PLAT754_ALERT_4_C Contact Calc     3.58000, Rep    3.577(7) ......  Senseless su
              C9   -H4      1.555   1.655
PLAT754_ALERT_4_C Contact Calc     2.05000, Rep    2.048(7) ......  Senseless su
              C10  -H2      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.26000, Rep    3.255(6) ......  Senseless su
              C10  -H4      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.14000, Rep    3.137(4) ......  Senseless su
              H1   -CL2     1.555   1.655
PLAT754_ALERT_4_C Contact Calc     2.81000, Rep    2.809(4) ......  Senseless su
              H1   -S1      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.02000, Rep    2.020(6) ......  Senseless su
              H1   -C5      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.25000, Rep    3.254(6) ......  Senseless su
              H1   -C6      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.23000, Rep    3.232(6) ......  Senseless su
              H1   -C8      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.04000, Rep    2.037(7) ......  Senseless su
              H1   -C9      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.26000, Rep    3.263(6) ......  Senseless su
              H2   -C5      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.57000, Rep    3.566(7) ......  Senseless su
              H2   -C6      1.555   1.655
PLAT754_ALERT_4_C Contact Calc     3.26000, Rep    3.262(6) ......  Senseless su
              H2   -C7      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.03000, Rep    2.026(6) ......  Senseless su
              H2   -C8      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.05000, Rep    2.048(7) ......  Senseless su
              H2   -C10     1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.51000, Rep    2.515(5) ......  Senseless su
              H3   -O1      1.555   1.554
PLAT754_ALERT_4_C Contact Calc     3.43000, Rep    3.427(5) ......  Senseless su
              H3   -N1      1.555   1.554
PLAT754_ALERT_4_C Contact Calc     3.26000, Rep    3.261(6) ......  Senseless su
              H3   -C5      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.05000, Rep    2.045(6) ......  Senseless su
              H3   -C6      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.03000, Rep    2.026(6) ......  Senseless su
              H3   -C8      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.26000, Rep    3.259(6) ......  Senseless su
              H3   -C9      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.58000, Rep    3.582(6) ......  Senseless su
              H3   -C9      1.555   2.665
PLAT754_ALERT_4_C Contact Calc     3.52000, Rep    3.515(3) ......  Senseless su
              H4   -CL4     1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.84000, Rep    2.835(4) ......  Senseless su
              H4   -S1      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.43000, Rep    3.431(5) ......  Senseless su
              H4   -C4      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.03000, Rep    2.035(6) ......  Senseless su
              H4   -C5      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     2.04000, Rep    2.043(6) ......  Senseless su
              H4   -C7      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.25000, Rep    3.247(6) ......  Senseless su
              H4   -C8      1.555   1.555
PLAT754_ALERT_4_C Contact Calc     3.58000, Rep    3.577(7) ......  Senseless su
              H4   -C9      1.555   1.455
PLAT754_ALERT_4_C Contact Calc     3.26000, Rep    3.255(6) ......  Senseless su
              H4   -C10     1.555   1.555

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  52 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
   3 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
  50 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; 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.

1,3,4,4-Tetrachloro-4-(4-chlorophenylsulfanyl)-2-nitrobuta-1,3-diene top

Crystal data top

C₁₀H₄Cl₅NO₂S	Z = 2
M_r = 379.46	F(000) = 376.00
Triclinic, P1	D_x = 1.727 Mg m⁻³
Hall symbol: -P 1	Melting point = 386–388 K
a = 6.6504 (4) Å	Mo Kα radiation, λ = 0.7107 Å
b = 10.7872 (3) Å	Cell parameters from 6436 reflections
c = 10.857 (4) Å	θ = 3.1–30.1°
α = 70.481 (4)°	µ = 1.13 mm⁻¹
β = 87.411 (8)°	T = 294 K
γ = 83.680 (7)°	Block, yellow
V = 729.6 (3) Å³	0.40 × 0.30 × 0.25 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3450 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.021
ω scans	θ_max = 30.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
T_min = 0.677, T_max = 0.760	k = −14→15
8204 measured reflections	l = −15→15
4303 independent reflections

Refinement top

Refinement on F	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.079	Chebychev polynomial with three parameters (Carruthers & Watkin, 1979): 9.9084, 2.2048 and 6.4348
wR(F²) = 0.085	(Δ/σ)_max = 0.009
S = 1.10	Δρ_max = 1.24 e Å⁻³
3450 reflections	Δρ_min = −0.77 e Å⁻³
176 parameters

Special details top

Geometry. Least Squares Planes ————– Plane number 1 ———–

Atoms Defining Plane Distance e.s.d. C1 [1;0;0;0] 0.1784 0.0020 C2 [1;0;0;0] -0.3781 0.0042 C3 [1;0;0;0] 0.1812 0.0020 C4 [1;0;0;0] -0.0613 0.0007

Additional Atoms Distance e.s.d.

Mean deviation from plane is 0.1997 angstrom Chi-squared: 9329.680 ————– Plane number 2 —————

Atoms Defining Plane Distance e.s.d. C5 [1;0;0;0] -0.0102 0.0026 C6 [1;0;0;0] 0.0087 0.0030 C7 [1;0;0;0] 0.0003 0.0032 C8 [1;0;0;0] -0.0069 0.0032 C9 [1;0;0;0] 0.0036 0.0035 C10 [1;0;0;0] 0.0071 0.0032

Additional Atoms Distance e.s.d.

Mean deviation from plane is 0.0061 angstrom Chi-squared: 15.255 Dihedral angles between least-squares planes ——————————–

plane plane angle e.s.d. 1 2 59.489 0.194

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

	x	y	z	U_iso*/U_eq
Cl1	−0.1743 (2)	−0.03972 (12)	0.8236 (1)	0.0945 (4)
Cl2	−0.2755 (2)	0.20470 (13)	0.60950 (12)	0.0820 (3)
Cl3	0.2609 (2)	0.04192 (12)	0.8303 (1)	0.0938 (4)
Cl4	0.2323 (3)	0.14109 (11)	0.45793 (12)	0.0961 (4)
Cl5	0.5769 (2)	0.27694 (13)	−0.10412 (12)	0.0897 (4)
S1	0.3263 (2)	0.41666 (8)	0.39865 (8)	0.0575 (2)
O2	0.2029 (5)	0.4758 (3)	0.6074 (3)	0.0717 (9)
O1	0.0587 (5)	0.3572 (3)	0.7825 (3)	0.0711 (8)
N1	0.1338 (5)	0.3733 (3)	0.6743 (3)	0.0554 (8)
C1	−0.0981 (8)	0.1058 (5)	0.7168 (4)	0.0772 (13)
C2	0.0791 (8)	0.1423 (4)	0.7181 (4)	0.0748 (13)
C3	0.1440 (6)	0.2659 (3)	0.6240 (3)	0.0581 (9)
C4	0.2248 (6)	0.2784 (3)	0.5043 (4)	0.0569 (9)
C5	0.3938 (6)	0.3702 (3)	0.2590 (3)	0.0558 (9)
C6	0.2498 (6)	0.3865 (4)	0.1646 (4)	0.0622 (10)
C7	0.3068 (7)	0.3572 (4)	0.0523 (4)	0.0642 (11)
C8	0.5061 (7)	0.3144 (3)	0.0362 (4)	0.0621 (10)
C9	0.6512 (7)	0.3006 (4)	0.1272 (4)	0.0710 (12)
C10	0.5929 (6)	0.3296 (4)	0.2395 (4)	0.0668 (11)
H1	0.6898	0.3212	0.3042	0.081*
H2	0.7879	0.2726	0.1123	0.086*
H3	0.2114	0.3676	−0.0139	0.078*
H4	0.1137	0.4167	0.1781	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1222 (11)	0.0700 (6)	0.0911 (8)	−0.0409 (7)	0.0331 (7)	−0.0211 (6)
Cl2	0.0688 (7)	0.0935 (8)	0.0757 (6)	−0.0177 (5)	−0.0111 (5)	−0.0129 (6)
Cl3	0.0921 (8)	0.0734 (7)	0.0921 (8)	−0.0097 (6)	−0.0301 (6)	0.0082 (6)
Cl4	0.1626 (13)	0.0636 (6)	0.0783 (7)	−0.0440 (7)	0.0476 (8)	−0.0410 (5)
Cl5	0.1246 (10)	0.0849 (7)	0.0705 (6)	−0.0210 (7)	0.0293 (6)	−0.0411 (6)
S1	0.0748 (6)	0.0516 (4)	0.0494 (4)	−0.0169 (4)	0.0077 (4)	−0.0188 (3)
O2	0.096 (2)	0.059 (1)	0.070 (2)	−0.025 (1)	0.012 (1)	−0.0313 (13)
O1	0.092 (2)	0.073 (2)	0.054 (1)	−0.006 (1)	0.0104 (13)	−0.0299 (12)
N1	0.063 (2)	0.055 (2)	0.053 (2)	−0.0051 (12)	0.0006 (12)	−0.0233 (12)
C1	0.099 (3)	0.076 (3)	0.062 (2)	−0.022 (2)	0.014 (2)	−0.028 (2)
C2	0.100 (3)	0.066 (2)	0.063 (2)	−0.017 (2)	0.012 (2)	−0.026 (2)
C3	0.076 (2)	0.049 (2)	0.053 (2)	−0.013 (2)	0.009 (2)	−0.0209 (13)
C4	0.071 (2)	0.048 (2)	0.057 (2)	−0.013 (1)	0.008 (2)	−0.0223 (13)
C5	0.070 (2)	0.052 (2)	0.048 (2)	−0.014 (2)	0.007 (1)	−0.0173 (13)
C6	0.066 (2)	0.063 (2)	0.058 (2)	−0.001 (2)	−0.003 (2)	−0.021 (2)
C7	0.084 (3)	0.061 (2)	0.049 (2)	−0.010 (2)	−0.002 (2)	−0.019 (2)
C8	0.086 (3)	0.047 (2)	0.054 (2)	−0.015 (2)	0.018 (2)	−0.0170 (13)
C9	0.073 (3)	0.074 (2)	0.069 (2)	−0.010 (2)	0.015 (2)	−0.028 (2)
C10	0.066 (2)	0.071 (2)	0.067 (2)	−0.010 (2)	0.002 (2)	−0.026 (2)

Geometric parameters (Å, º) top

Cl1—C1	1.724 (5)	C3—C4	1.354 (5)
Cl2—C1	1.704 (5)	C5—C6	1.389 (6)
Cl3—C2	1.755 (5)	C5—C10	1.378 (6)
Cl4—C4	1.711 (4)	C6—C7	1.385 (6)
Cl5—C8	1.735 (4)	C6—H4	0.950
S1—C4	1.733 (3)	C7—C8	1.378 (6)
S1—C5	1.774 (4)	C7—H3	0.950
O2—N1	1.227 (4)	C8—C9	1.374 (6)
O1—N1	1.221 (4)	C9—C10	1.385 (7)
N1—C3	1.431 (5)	C9—H2	0.950
C1—C2	1.285 (8)	C10—H1	0.950
C2—C3	1.478 (5)

Cl1···Cl2	2.909 (2)	C4···H4	3.431 (5)
Cl1···Cl3	3.127 (2)	C5···Cl4	2.956 (3)
Cl1···C2	2.657 (5)	C5···C4	2.747 (5)
Cl2···Cl1	2.909 (2)	C5···C7	2.395 (6)
Cl2···C2	2.603 (5)	C5···C8	2.735 (6)
Cl2···C3	2.959 (4)	C5···C9	2.399 (6)
Cl2···C4ⁱ	3.484 (4)	C5···H1	2.020 (6)
Cl2···C4	3.555 (4)	C5···H2	3.263 (6)
Cl2···H1ⁱ	3.137 (4)	C5···H3	3.261 (6)
Cl3···Cl1	3.127 (2)	C5···H4	2.035 (6)
Cl3···O1	3.394 (3)	C6···Cl4	3.400 (4)
Cl3···N1	3.432 (3)	C6···S1	2.744 (5)
Cl3···C1	2.651 (5)	C6···C4	3.478 (5)
Cl3···C3	2.754 (3)	C6···C8	2.381 (6)
Cl4···S1	2.956 (2)	C6···C9	2.785 (6)
Cl4···C1	3.433 (5)	C6···C10	2.402 (6)
Cl4···C2	2.963 (5)	C6···H1	3.254 (6)
Cl4···C3	2.601 (4)	C6···H2ⁱ	3.566 (7)
Cl4···C5	2.956 (3)	C6···H3	2.045 (6)
Cl4···C6	3.400 (4)	C7···O1ⁱⁱⁱ	3.426 (5)
Cl4···C10	3.585 (4)	C7···C5	2.395 (6)
Cl4···H4	3.515 (3)	C7···C9	2.410 (6)
S1···Cl4	2.956 (2)	C7···C9^iv	3.588 (6)
S1···O2	2.626 (3)	C7···C10	2.768 (6)
S1···N1	3.109 (3)	C7···H2	3.262 (6)
S1···C3	2.759 (3)	C7···H4	2.043 (6)
S1···C6	2.744 (5)	C8···C5	2.735 (6)
S1···C10	2.730 (5)	C8···C6	2.381 (6)
S1···H1	2.809 (4)	C8···C10	2.368 (6)
S1···H4	2.835 (4)	C8···H1	3.232 (6)
O2···S1	2.626 (3)	C8···H2	2.026 (6)
O2···O1	2.157 (4)	C8···H3	2.026 (6)
O2···C2	3.569 (5)	C8···H4	3.247 (6)
O2···C3	2.286 (5)	C9···C5	2.399 (6)
O2···C4	2.706 (5)	C9···C6	2.785 (6)
O1···Cl3	3.394 (3)	C9···C7	2.410 (6)
O1···O2	2.157 (4)	C9···C7^iv	3.588 (6)
O1···C1	3.306 (7)	C9···H1	2.037 (7)
O1···C2	2.624 (6)	C9···H3	3.259 (6)
O1···C3	2.274 (5)	C9···H3^iv	3.582 (6)
O1···C4	3.504 (5)	C9···H4ⁱⁱ	3.577 (7)
N1···Cl3	3.432 (3)	C10···Cl4	3.585 (4)
N1···S1	3.109 (3)	C10···S1	2.730 (5)
N1···C1	3.308 (6)	C10···C6	2.402 (6)
N1···C2	2.441 (6)	C10···C7	2.768 (6)
N1···C4	2.419 (5)	C10···C8	2.368 (6)
C1···Cl3	2.651 (5)	C10···H2	2.048 (7)
C1···Cl4	3.433 (5)	C10···H4	3.255 (6)
C1···O1	3.306 (7)	H1···Cl2ⁱⁱ	3.137 (4)
C1···N1	3.308 (6)	H1···S1	2.809 (4)
C1···C3	2.427 (6)	H1···C5	2.020 (6)
C1···C4	3.311 (6)	H1···C6	3.254 (6)
C2···Cl1	2.657 (5)	H1···C8	3.232 (6)
C2···Cl2	2.603 (5)	H1···C9	2.037 (7)
C2···Cl4	2.963 (5)	H2···C5	3.263 (6)
C2···O2	3.569 (5)	H2···C6ⁱⁱ	3.566 (7)
C2···O1	2.624 (6)	H2···C7	3.262 (6)
C2···N1	2.441 (6)	H2···C8	2.026 (6)
C2···C4	2.513 (5)	H2···C10	2.048 (7)
C3···Cl2	2.959 (4)	H3···O1ⁱⁱⁱ	2.515 (5)
C3···Cl3	2.754 (3)	H3···N1ⁱⁱⁱ	3.427 (5)
C3···Cl4	2.601 (4)	H3···C5	3.261 (6)
C3···S1	2.759 (3)	H3···C6	2.045 (6)
C3···O2	2.286 (5)	H3···C8	2.026 (6)
C3···O1	2.274 (5)	H3···C9	3.259 (6)
C3···C1	2.427 (6)	H3···C9^iv	3.582 (6)
C4···Cl2	3.555 (4)	H4···Cl4	3.515 (3)
C4···Cl2ⁱⁱ	3.484 (4)	H4···S1	2.835 (4)
C4···O2	2.706 (5)	H4···C4	3.431 (5)
C4···O1	3.504 (5)	H4···C5	2.035 (6)
C4···N1	2.419 (5)	H4···C7	2.043 (6)
C4···C6	3.311 (6)	H4···C8	3.247 (6)
C4···C2	2.513 (5)	H4···C9ⁱ	3.577 (7)
C4···C5	2.747 (5)	H4···C10	3.255 (6)
C4···C6	3.478 (5)

C4—S1—C5	103.1 (2)	C10—C5—S1	119.5 (3)
C3—N1—O2	118.5 (3)	C7—C6—H4	120.9
C3—N1—O1	117.9 (3)	C7—C6—C5	119.4 (4)
O2—N1—O1	123.6 (4)	H4—C6—C5	119.7
C2—C1—Cl1	123.3 (4)	C8—C7—H3	119.9
C2—C1—Cl2	120.5 (3)	C8—C7—C6	119.0 (4)
Cl1—C1—Cl2	116.1 (3)	H3—C7—C6	121.1
C3—C2—Cl3	116.6 (4)	C9—C8—Cl5	118.7 (3)
C3—C2—C1	122.8 (4)	C9—C8—C7	122.3 (4)
Cl3—C2—C1	120.6 (3)	Cl5—C8—C7	119.0 (3)
C4—C3—N1	120.5 (3)	C10—C9—H2	121.5
C4—C3—C2	125.1 (4)	C10—C9—C8	118.3 (4)
N1—C3—C2	114.1 (3)	H2—C9—C8	120.3
S1—C4—C3	126.2 (3)	H1—C10—C5	119.2
C6—C5—C10	120.5 (4)	H1—C10—C9	120.3
C6—C5—S1	119.8 (3)	C5—C10—C9	120.5 (4)

C5—S1—C4—Cl4	4.6 (3)	C10—C5—C6—C7	2.1 (5)
C5—S1—C4—C3	−177.6 (3)	C10—C5—C6—H4	−178.3
C4—S1—C5—C6	84.8 (3)	S1—C5—C10—C9	−176.1 (3)
C4—S1—C5—C10	−101.0 (3)	S1—C5—C10—H1	4.3
O2—N1—C3—C2	173.1 (4)	C6—C5—C10—C9	−1.9 (6)
O2—N1—C3—C4	−1.2 (5)	C6—C5—C10—H1	178.5
O1—N1—C3—C2	−6.0 (5)	C5—C6—C7—C8	−0.9 (6)
O1—N1—C3—C4	179.7 (3)	C5—C6—C7—H3	−179.9
Cl1—C1—C2—Cl3	1.1 (8)	H4—C6—C7—C8	179.5
Cl1—C1—C2—C3	178.6 (4)	H4—C6—C7—H3	0.7
Cl2—C1—C2—Cl3	179.0 (4)	C6—C7—C8—Cl5	179.6 (3)
Cl2—C1—C2—C3	−3.5 (8)	C6—C7—C8—C9	−0.5 (6)
Cl3—C2—C3—N1	−83.0 (5)	H3—C7—C8—Cl5	−1.5
Cl3—C2—C3—C4	91.0 (5)	H3—C7—C8—C9	178.4
C1—C2—C3—N1	99.4 (6)	Cl5—C8—C9—C10	−179.4 (3)
C1—C2—C3—C4	−86.6 (6)	Cl5—C8—C9—H2	1.2
N1—C3—C4—Cl4	178.7 (3)	C7—C8—C9—C10	0.7 (6)
N1—C3—C4—S1	0.8 (6)	C7—C8—C9—H2	−178.7
C2—C3—C4—S1	−172.9 (3)	C8—C9—C10—C5	0.5 (6)
C2—C3—C4—Cl4	5.0 (5)	C8—C9—C10—H1	−179.9
S1—C5—C6—C7	176.3 (3)	H2—C9—C10—C5	179.9
S1—C5—C6—H4	−4.2	H2—C9—C10—H1	−0.5

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, y, z−1; (iv) −x+1, −y+1, −z.

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1,3,4,4-Tetra­chloro-4-(4-chloro­phenyl­sulfan­yl)-2-nitro­buta-1,3-diene

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1,3,4,4-Tetrachloro-4-(4-chlorophenylsulfanyl)-2-nitrobuta-1,3-diene