1-(3-Chlorophenyl)-3-(2,6-dichlorobenzoyl)thiourea

The structure of the title compound, C14H9Cl3N2OS, is composed of discrete molecules with bond lengths and angles quite typical for thiourea compounds of this class. The plane containing the thiocarbonyl and carbonyl groups subtends dihedral angles of 48.19 (3) and 87.51 (3)° with the planes formed by the 3-chloro and 2,6-dichlorophenyl rings, respectively; the dihedral angle between the two benzene ring planes is 45.32 (3)°. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation and the molecules form intermolecular N—H⋯S and N—H⋯O hydrogen bonds, generating a sheet along the a axis.

The structure of the title compound, C 14 H 9 Cl 3 N 2 OS, is composed of discrete molecules with bond lengths and angles quite typical for thiourea compounds of this class. The plane containing the thiocarbonyl and carbonyl groups subtends dihedral angles of 48.19 (3) and 87.51 (3) with the planes formed by the 3-chloro and 2,6-dichlorophenyl rings, respectively; the dihedral angle between the two benzene ring planes is 45.32 (3) . An intramolecular N-HÁ Á ÁO hydrogen bond stabilizes the molecular conformation and the molecules form intermolecular N-HÁ Á ÁS and N-HÁ Á ÁO hydrogen bonds, generating a sheet along the a axis.

Comment
The background to this study has been set out in our previous work on the structural chemistry of N,N'-disubstituted thioureas (Khawar Rauf et al., 2006a, 2007. Herein, as a continuation of these studies, the structure of the title compound, (I), is described.
In the structure of the title compound ( Fig. 1), bond lengths and bond angles can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002) and some related structures (Khawar Rauf et al., 2006b). The molecule exists in the thione form with typical thiourea C-S and C-O bonds, as well as shortened C-N bonds. The thiocarbonyl and carbonyl groups are almost coplanar. The molecule features an intramolecular N-H···O hydrogen bond in the crystal structure. The molecules lying about inversions centers associate via N-H···S intermolecular hydrogen bonds to form dimers on one side and a similar association via N-H···O hydrogen bonding on the other side thus result in a sheet of molecules of (I) along the a<ι>-axis (Table 1; Fig. 2).
The reaction mixture was then poured into acidified (pH 4) water (approx. 300 ml) and stirred well. The solid product was separated, washed with deionized water and purified by recrystallization from methanol/1,1-dichloromethane (1:10 v/v) to give fine crystals of (I), with an overall yield of 85%.

Refinement
Hydrogen atoms bonded to C were included in calculated positions and refined as riding on their parent C atom with C-H = 0.95 Å and U iso (H) = 1.2U eq (C). The H atoms bonded to N were freely refined.