4-Bromo-N-(diethylcarbamothioyl)benzamide

The synthesis of the title compound, C12H15BrN2OS, involves the reaction of 4-bromobenzoyl chloride with potassium thiocyanate in dry acetone, followed by condensation of 4-bromobenzoyl isothiocyanate with diethylamine. The carbonyl and thiocarbonyl bond lengths indicate that these correspond to double bonds. The short C—N bond lengths reveal the effects of resonance in this part of the molecule. The conformation of the molecule with respect to the thiocarbonyl and carbonyl units is twisted, with torsion angles of −5.7 (3) and 87.2 (2)°. The N atom of the diethylamine group is sp 2-hybridized: the sum of the angles around the N atom is 359.97 (14)°. The two diethyl groups are twisted in + and − antiperiplanar conformations with angles of −179.89 and 179.92°. In the crystal structure, the molecules form infinite chains via an intermolecular N—H⋯O interaction.

The synthesis of the title compound, C 12 H 15 BrN 2 OS, involves the reaction of 4-bromobenzoyl chloride with potassium thiocyanate in dry acetone, followed by condensation of 4-bromobenzoyl isothiocyanate with diethylamine. The carbonyl and thiocarbonyl bond lengths indicate that these correspond to double bonds. The short C-N bond lengths reveal the effects of resonance in this part of the molecule. The conformation of the molecule with respect to the thiocarbonyl and carbonyl units is twisted, with torsion angles of À5.7 (3) and 87.2 (2) . The N atom of the diethylamine group is sp 2hybridized: the sum of the angles around the N atom is 359.97 (14) . The two diethyl groups are twisted in + and À antiperiplanar conformations with angles of À179.89 and 179.92 . In the crystal structure, the molecules form infinite chains via an intermolecular N-HÁ Á ÁO interaction.  Aamrani et al. (1998Aamrani et al. ( , 1999; Arslan et al. (2006) Table 1 Hydrogen-bond geometry (Å , ).

Comment
Transition metal complexes bearing thiourea ligand or its derivatives have been one of the highlights in coordination chemistry, which are used as reactant for extraction of some transition metal ions (Koch, 2001;El Aamrani et al., 1998, 1999. Moreover, the growing interest for thiourea derivative ligands and their metal complexes result from the important role they play in biological systems (Yuan et al., 2001;Zhang et al., 2004;Weiqun et al., 2004).
Recently, our research has focussed on the chemical and physical properties of thiourea derivatives and their metal complexes (Arslan et al., 2006;Arslan, Flörke & Külcü, 2007;Arslan, Flörke, Külcü & Binzet, 2007). In the present work, we report the crystal structure of 4-bromo-N-(diethylcarbamothioyl)benzamide, (I). The molecular structure of the title compound is depicted in Fig. 1.

Experimental
The title compound was prepared with a procedure similar to that reported in the literature (Arslan, Külcü & Flörke, 2003;Özer et al., 2009) H atoms bound to C atoms were placed geometrically and allowed to ride on their parent atoms, with C-H = 0.95-0.99 Å and U iso (H) = 1.2 or 1.5 U eq (C). The nitrogen-bound H atom was located in a difference Fourier map and refined freely.
Figures Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.