organic papers o800 Ibis et al. C 10 H 4 Cl 5 NO 2 S doi:10.1107/S1600536806001838 Acta Cryst. (2006). E62, o800–o801 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 1,3,4,4-Tetrachloro-4-(4-chlorophenyl- sulfanyl)-2-nitrobuta-1,3-diene Cemil Ibis,* M. Cigdem Sayil and N. Gulsah Deniz Istanbul University, Faculty of Engineering, Department of Chemistry, 34320 Avcilar–Istanbul, Turkey Correspondence e-mail: ibiscml@istanbul.edu.tr Key indicators Single-crystal X-ray study T = 294 K Mean (C–C) = 0.006 A ˚ R factor = 0.079 wR factor = 0.085 Data-to-parameter ratio = 19.6 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e. Received 3 January 2006 Accepted 17 January 2006 # 2006 International Union of Crystallography All rights reserved The molecule of the title compound, C 10 H 4 Cl 5 NO 2 S, is not planar. The chlorophenyl ring and the butadiene group are inclined at an angle of 59.5 (1) . Comment The chemistry of nitro compounds, especially their halogen derivatives, has been intensively studied in recent decades. These highly reactive subtances have been used to develop preparative methods for the synthesis of complex polyfunc- tional derivatives of different classes. However, there are only a few reports on the crystal structures of halogened nitro- butadiene compounds. The title compound, (I), was synthe- sized from 2-nitropentachlorobutadiene and p-chloro- thiophenol (Ibis & Goksel, 1994). Crystallographic analysis was carried out and the results are presented in this paper. The molecule is not planar. The chlorophenyl ring and the butadiene group are inclined at an angle of 59.5 (1) . The C— C bond lengths of the butadiene chain agree well with corresponding distances in a similar compound (Surange et al. , 1997). Experimental p-Chlorothiophenol (1.06 g, 7.37 mmol) and 2-nitropentachloro-1,3- butadiene (2 g, 7.37 mmol) were stirred for 24 h at room temperature. The product was extracted with chloroform; the organic layer was separated and washed with distilled water (3 30 ml) and dried with Na 2 SO 4 . The solvent was evaporated and the residue was purified by cystallization from ethanol (yield: 2.2 g, 79%; m.p. 386–388 K). Crystal data C 10 H 4 Cl 5 NO 2 S M r = 379.46 Triclinic, P 1 a = 6.6504 (4) A ˚ b = 10.7872 (3) A ˚ c = 10.857 (4) A ˚ = 70.481 (4) = 87.411 (8) = 83.680 (7) V = 729.6 (3) A ˚ 3 Z =2 D x = 1.727 Mg m 3 Mo K radiation Cell parameters from 6436 reflections = 3.1–30.1 = 1.13 mm 1 T = 293.5 K Block, yellow 0.40 0.30 0.25 mm