Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050957/im2039sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050957/im2039Isup2.hkl |
CCDC reference: 669141
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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).
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).
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).
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).
Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. |
C18H14Cl3NO2S2 | F(000) = 912.00 |
Mr = 446.79 | Dx = 1.486 Mg m−3 |
Monoclinic, P21/n | Melting point = 392–393 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.7107 Å |
a = 13.885 (1) Å | Cell parameters from 5659 reflections |
b = 6.8246 (6) Å | θ = 2.9–25.3° |
c = 21.313 (2) Å | µ = 0.68 mm−1 |
β = 98.630 (5)° | T = 294 K |
V = 1996.7 (3) Å3 | Needle, yellow |
Z = 4 | 0.40 × 0.20 × 0.10 mm |
Rigaku R-AXIS RAPID S diffractometer | 3254 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.086 |
ω scans | θmax = 25.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −16→16 |
Tmin = 0.849, Tmax = 0.935 | k = −8→7 |
69322 measured reflections | l = −25→25 |
3653 independent reflections |
Refinement on F | 0 restraints |
R[F2 > 2σ(F2)] = 0.036 | H-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 reflections | Δρmax = 0.38 e Å−3 |
235 parameters | Δρmin = −0.25 e Å−3 |
C18H14Cl3NO2S2 | V = 1996.7 (3) Å3 |
Mr = 446.79 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.885 (1) Å | µ = 0.68 mm−1 |
b = 6.8246 (6) Å | T = 294 K |
c = 21.313 (2) Å | 0.40 × 0.20 × 0.10 mm |
β = 98.630 (5)° |
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 = 0.935 | Rint = 0.086 |
69322 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.049 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.38 e Å−3 |
3254 reflections | Δρmin = −0.25 e Å−3 |
235 parameters |
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). |
x | y | z | Uiso*/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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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 formula | C18H14Cl3NO2S2 |
Mr | 446.79 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 13.885 (1), 6.8246 (6), 21.313 (2) |
β (°) | 98.630 (5) |
V (Å3) | 1996.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 0.40 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID S |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.849, 0.935 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 69322, 3653, 3254 |
Rint | 0.086 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.049, 1.12 |
No. of reflections | 3254 |
No. of parameters | 235 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
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)°.