Research Article: (1Z,2E)-N′-{1-[2-(4-Bromo­phen­yl)hydrazin-1-yl­idene]-1-chloro­propan-2-yl­idene}thio­phene-2-carbohydrazide

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Hoong-Kun Fun, Suchada Chantrapromma, Hatem A. Abdel-Aziz.


In the title compound, C14H12BrClN4OS, the thienyl ring is disordered over two orientations with a site-occupancy ratio of 0.853 (2):0.147 (2). The mol­ecule is roughly planar, with the dihedral angles between the thienyl and benzene rings being 6.24 (16) and 9.7 (11)° for the major and minor components, respectively. The central fragment is almost planar [r.m.s. deviation = 0.0275 (2) Å for the ten non-H atoms]. The mean plane through this middle unit makes a dihedral angle of 2.71 (7)° with the benzene ring, whereas these values are 4.46 (15) and 7.7 (11)° for the major and minor components of the thienyl ring, respectively. In the crystal, mol­ecules are linked into dimers by pairs of N—H⋯O hydrogen bonds, forming R22(8) ring motifs. These dimers are arranged into sheets parallel to the ac plane.

Partial Text

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to and the biological activity of (1Z,2E)-N-(ar­yl)propane­hydrazonoyl chlorides, see: Abdel-Aziz & Mekawey (2009 ▶); Abdel-Aziz et al. (2010 ▶). For a related structure, see: Abdel-Aziz et al. (2012 ▶). For the stability of the temperature controller, see: Cosier & Glazer (1986 ▶).