Research Article: 1-{(E)-[4-(4-Meth­oxy­phen­yl)butan-2-yl­idene]amino}-3-methyl­thio­urea

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].

Partial Text

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 ▶).