Date Published: June 01, 2010
Publisher: International Union of Crystallography
Author(s): Afsheen Arshad, Hasnah Osman, Kit Lam Chan, Jia Hao Goh, Hoong-Kun Fun.
The title compound, C12H10BrN3O2S, exists in an E configuration with respect to the C=N bond. The approximately planar 2H-chromene ring system [maximum deviation = 0.059 (1) Å] is inclined at a dihedral angle of 17.50 (5)° with respect to the mean plane through the thiosemicarbazide unit and an intramolecular N—H⋯N hydrogen bond generates an S(5) ring. In the crystal structure, adjacent molecules are linked by N—H⋯S hydrogen bonds, forming  chains built up from R22(8) loops, such that each S atom accepts two such bonds. These chains are further interconnected into sheets parallel to the ab plane via short Br⋯O interactions [3.0732 (13) Å] and a π–π aromatic stacking interaction [3.7870 (8) Å] is also observed.
For general background to and applications of the title thiosemicarbazide compound, see: Anderson et al. (2002 ▶); Chulian et al. (2009 ▶); Desai et al. (1984 ▶); Finn et al. (2004 ▶); Hofmanová et al. (1998 ▶); Hoult & Payá (1996 ▶); Kimura et al. (1985 ▶); Laffitte et al. (2002 ▶); Mitscher (2002 ▶); Moffett (1964 ▶); Pillai et al. (1999 ▶); Shukla et al. (1984 ▶); Tassies et al. (2002 ▶); Weber et al. (1998 ▶). For the preparation, see: Moamen et al. (2009 ▶). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For a related structure, see: Arshad et al. (2010 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).