2-Bromo-N-(dibenzylcarbamothioyl)benzamide

The 2-bromobenzoyl group in the title compound, C22H19BrN2OS, adopts an E conformation with respect to the thiono S atom across the N—C bond. In the crystal structure, the molecule is stablized by N—H⋯O intermolecular hydrogen bonds, forming a one-dimensional chain along the b axis.

The 2-bromobenzoyl group in the title compound, C 22 H 19 BrN 2 OS, adopts an E conformation with respect to the thiono S atom across the N-C bond. In the crystal structure, the molecule is stablized by N-HÁ Á ÁO intermolecular hydrogen bonds, forming a one-dimensional chain along the b axis.

Related literature
For related structures, see: Yamin & Hassan (2004); Hassan et al. (2008aHassan et al. ( ,b,c, 2009 san, 2004). The molecule has the 2-bromobenzoyl group adopting an E conformation, with respect to the thiono S atom across the N1-C8 bond, whereas both the phenyl ring of the dibenzylamine group adopt E and Z conformation relative to the S atom across the N2-C8 bond (Fig. 1). The phenyl ring, (C1-C6), and the thiourea fragment, (S1/N1/N2/C8), are essentially planar and the dihedral angle between them is 72.9 (2)°. The bond lengths and angles in the molecules are in normal ranges (Allen et al., 1987).

Experimental
The title compound was synthesized according to a previously reported compound (Hassan et al., 2008a). A colourless crystal, suitable for X-ray crystallography, was obtained by a slow evaporation from methanolic solution at room temperature (yield 83%).

Refinement
H atoms of both C and N atoms were positioned geometrically and allowed to ride on their parent atoms, with U iso = 1.2U eq (C) for aromatic 0.93 Å, U iso = 1.2U eq (C) for CH 2 0.97 Å, U iso = 1.2U eq (N) for N-H 0.86 Å. Fig. 1. The molecular structure of (I), with the atoms labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

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.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.