Crystal structures ofN-[(4-phenylthiazol-2-yl)carbamothioyl]benzamide andN-{[4-(4-bromophenyl)thiazol-2-yl]carbamothioyl}benzamide from synchrotron X-ray diffraction

Abstract

The title compounds, C17H13N3OS2, (I), and C17H12BrN3OS2, (II), are potential active pharmaceutical ingredients. Compound (I) comprises two almost planar fragments. The first is the central (carbamothioyl)amide (r.m.s. deviation = 0.038 Å), and the second consists of the thiazole and two phenyl rings (r.m.s. deviation = 0.053 Å). The dihedral angle between these planes is 15.17 (5)°. Unlike (I), compound (II) comprises three almost planar fragments. The first is the centralN-(thiazol-2-ylcarbamothioyl)amide (r.m.s. deviation = 0.084 Å), and the two others comprise the bromophenyl and phenyl substituents, respectively. The dihedral angles between the central and two terminal planar fragments are 21.58 (7) and 17.90 (9)°, respectively. Both (I) and (II) feature an intramolecular N—H...O hydrogen bond, which closes anS(6) ring. In the crystal of (I), molecules form hydrogen-bonded layers parallel to (100) mediated by N—H...S and C—H...O hydrogen bonds. In the crystal of (II), molecules form a three-dimensional framework mediated by N—H...Br and C—H...O hydrogen bonds, as well as secondary S...Br [3.3507 (11) Å] and S...S [3.4343 (14) Å] interactions.