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

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 central N-(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 an S(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. © Wang et al. 2016.