4-Bromo-N-(di-n-propylcarbamothioyl)benzamide

Abstract

The synthesis of the title compound, C14H19BrN2OS, involves the reaction of 4-bromobenzoyl chloride with potassium thiocyanate in acetone followed by condensation of the resulting 4-bromobenzoyl isothiocyanate with di-n-propylamine. Typical thiourea carbonyl and thiocarbonyl double bonds, as well as shortened C-N bonds, are observed in the title compound. The short C-N bond lengths in the centre of the molecule reveal the effects of resonance in this part of the molecule. The asymmetric unit of the title compound contains two crystallographically independent molecules, A and B. There is very little difference between the bond lengths and angles of these molecules. In molecule B, one di-n-propyl group is twisted in a -antiperiplanar conformation with C C-C-H = -179.1 (3)degrees and the other adopts a -synclinal conformation with C-C-C-H = -56.7 (4)degrees; in molecule A the two di-n-propyl groups are twisted in + and-antiperiplanar conformations, with C-C-C-H =-179.9 (3) and 178.2 (3)degrees, respectively. In the crystal, the molecules are linked into dimeric pairs via pairs of N-H center dot center dot center dot S hydrogen bonds.