Crystal structures of N-[(4-phenyl-thia-zol-2-yl)carbamo-thio-yl]benzamide and N-{[4-(4-bromo-phen-yl)thia-zol-2-yl]carbamo-thio-yl}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 (carbamo-thio-yl)amide (r.m.s. deviation = 0.038?Å), and the second consists of the thia-zole 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-(thia-zol-2-ylcarbamo-thio-yl)amide (r.m.s. deviation = 0.084?Å), and the two others comprise the bromo-phenyl 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 intra-molecular N-H?O hydrogen bond, which closes an S(6) ring. In the crystal of (I), mol-ecules form hydrogen-bonded layers parallel to (100) mediated by N-H?S and C-H?O hydrogen bonds. In the crystal of (II), mol-ecules 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] inter-actions.

SUBMITTER: Gantimurova ES 

PROVIDER: S-EPMC5120721 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature