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

Ekaterina S Gantimurova; Alexander S Bunev; Kristina Yu Talina; Gennady I Ostapenko; Pavel V Dorovatovskii; Nikolai N Lobanov; Victor N Khrustalev

doi:10.1107/S2056989016013396

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

Acta Crystallogr E Crystallogr Commun. 2016 Aug 26;72(Pt 9):1343-1347. doi: 10.1107/S2056989016013396. eCollection 2016 Sep 1.

Authors

Ekaterina S Gantimurova¹, Alexander S Bunev¹, Kristina Yu Talina¹, Gennady I Ostapenko¹, Pavel V Dorovatovskii², Nikolai N Lobanov³, Victor N Khrustalev⁴

Affiliations

¹ Laboratory of Functional Heterocyclic Compounds, Togliatti State University, 14 Belorusskaya St., Togliatti 445020, Russian Federation.
² National Research Centre "Kurchatov Institute", 1 Acad. Kurchatov Sq., Moscow 123182, Russian Federation.
³ Inorganic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklay St., Moscow 117198, Russian Federation.
⁴ Inorganic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklay St., Moscow 117198, Russian Federation; X-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., B-334, Moscow 119991, Russian Federation.

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.

Keywords: crystal structure; hydrogen bonds; synchrotron; thiazoles; thiourea.