organic papers o1264 Rauf et al. C 14 H 10 Cl 2 N 2 OS doi:10.1107/S1600536806007343 Acta Cryst. (2006). E62, o1264–o1265 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 1-Benzoyl-3-(2,6-dichlorophenyl)thiourea M. Khawar Rauf, a Amin Badshah, a * Ulrich Flo ¨rke, b Aamer Saeed a and M. Adeel Saeed a a Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and b Department Chemie, Fakulta ¨t fu ¨r Naturwissenschaften, Universita ¨t Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany Correspondence e-mail: aminbadshah@yahoo.com Key indicators Single-crystal X-ray study T = 120 K Mean (C–C) = 0.002 A ˚ R factor = 0.028 wR factor = 0.078 Data-to-parameter ratio = 18.6 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e. Received 16 February 2006 Accepted 28 February 2006 # 2006 International Union of Crystallography All rights reserved The asymmetric unit of the title compound, C 14 H 10 Cl 2 N 2 OS, contains two independent molecules with slightly different conformations with respect to the aromatic ring planes. The two independent molecules form dimers via intermolecular N—HS hydrogen bonds; the dimers are stacked along [100]. Comment N,N 0 -Disubstituted thiourea derivatives have attracted atten- tion due to their coordination behavior with transition metals. The complexation capacity of thiourea derivatives has been reported in several studies (Schuster et al., 1990). In addition, thioureas have been shown to possess antibacterial, anti- fungal, antitubercular, antithyroid and insecticidal properties (Madan et al., 1991). The biological activities of complexes with thiourea derivatives have been successfully screened for various biological activties (Frech et al., 1970). The molecular structure of (I) is shown in Fig. 1. There are two independent molecules (A and B) in the asymmetric unit having slightly different geometries. Within each molecule, the dihedral angles formed between the phenyl and benzene rings are 72.43 (4) and 75.11 (4) for molecules A and B, respec- tively. Intramolecular N—HO hydrogen bonds (Table 2) appear to control the essentially planar conformation of the central thiourea units of each molecule. In the crystal struc- ture, independent molecules are linked by two intermolecular N—HS hydrogen bonds to form dimers which are stacked along [100] (Fig. 2). The shortest C—HCl distance is 2.89 A ˚ and there are no significant – stacking interactions. The 2,6- dichloro substitution in (I) does not lead to any significant changes in bond lengths compared to the molecular structure of the related 2-chlorophenyl compound (Yamin & Yusof, 2003). Experimental A solution of benzoyl chloride (1.50 g, 10 mmol) in acetone (50 ml) was added dropwise to a suspension of KSCN ((1.00 g, 10 mmol) in acetone (30 ml). The reaction mixture was heated under reflux for 45 min, and then cooled to room temperature. Afterwards, a solution