Crystal structure of 1-(1,3-benzothiazol-2-yl)-3-(4-bromobenzoyl)thiourea

The chemical reaction of 4-bromobenzoylchloride and 2-aminothiazole in the presence of potassium thiocyanate yielded a white solid formulated as C 15 H 10 BrN 3 OS 2 , which consists of 4-bromobenzamido and 2-benzothiazolyl moieties connected by a thiourea group. The 4-bromobenzamido and 2-benzothiazolyl moieties are in a trans conformtion (sometimes also called s -trans due to the single bond) with respect to the N—C bond. The dihedral angle between the mean planes of the 4-bromophenyl and the 2-benzothiazolyl units is 10.45 (11)°. The thiourea moiety, —C—NH—C(=S) —NH— fragment forms a dihedral angle of 8.64 (12)° with the 4-bromophenyl ring and is almost coplanar with the 2-benzothiazolyl moiety, with a dihedral angle of 1.94 (11)°. The molecular structure is stabilized by intramolecular N—H...O hydrogen bonds, resulting in the formation of an S (6) ring. In the crystal, pairs of adjacent molecules interact via intermolecular hydrogen bonds of type C—H...N, C—H...S and N—H...S, resulting in molecular layers parallel to the ac plane.