Date Published: May 01, 2012
Publisher: International Union of Crystallography
Author(s): Ming-Yueh Tan, Thahira Begum S. A. Ravoof, Mohamed Ibrahim Mohamed Tahir, Karen A. Crouse, Edward R. T. Tiekink.
Two independent molecules comprise the asymmetric unit of the title compound, C13H19N3OS, which differ in the conformations of the residues linking the thiourea and the terminal benzene ring, as manifested in the Cm—Cm—Ca—Ca torsion angles [78.03 (16) and −93.64 (16)°, respectively; m = methylene and a = aromatic]. The dihedral angles [84.40 (4) and 88.28 (5)°] formed between the thiourea residue and the benzene ring indicate an almost orthogonal relationship. In each thiourea residue, the N—H hydrogen atoms are anti, and the terminal N—H hydrogen atom forms an intramolecular N—H⋯N hydrogen bond with the imine-N atom. In each case, the conformation about the imine C=N double bond [1.2812 (17) and 1.2801 (17) Å] is E. In the crystal, the molecules are connected by N—H⋯S hydrogen bonds and these are connected into four molecule aggregates via N—H⋯O hydrogen bonds, which are assembled into a two-dimensional array parallel to (011) via C—H⋯π and π–π interactions [ring centroid–centroid distance = 3.8344 (9) Å].
For background to chalcone thiosemicarbazides, see: Zhang et al. (2011 ▶). For background to hydrazinecarbodithioates, see: Khoo et al. (2005 ▶); Chan et al. (2008 ▶); Ravoof et al. (2010 ▶). For related syntheses, see: Tian et al. (1997 ▶); Tarafder et al. (2002 ▶).