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.

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