Date Published: May 01, 2012
Publisher: International Union of Crystallography
Author(s): Gunay Z. Mammadova, Zhanna V. Matsulevich, Vladimir K. Osmanov, Alexander V. Borisov, Victor N. Khrustalev.
The title compound C8H8N2Se, is the product of the reaction of 2-chloro-1-methylbenzimidazole with sodium hydroselenide. The molecule is almost planar (r.m.s. deviation = 0.041 Å) owing to the presence of the long chain of conjugated bonds (Se=C—NMe—C=C—C=C—C=C—NH). The C=Se bond length [1.838 (2) Å] corresponds well to those found in the close analogs and indicates its pronounced double-bond character. In the crystal, molecules form helicoidal chains along the b axis by means of N—H⋯Se hydrogen bonds.
For selones as potential antithyroid drugs, see: Taurog et al. (1994 ▶); Roy & Mugesh (2005 ▶, 2006 ▶); Roy et al. (2007 ▶, 2011 ▶). For related compounds, see: Guziec & Guziec (1994 ▶); Husebye et al. (1997 ▶); Aydin et al. (1999 ▶); Akkurt et al. (2004 ▶, 2011 ▶); Landry et al. (2006 ▶); Nakanishi et al. (2008 ▶); Mammadova et al. (2011 ▶). For hypervalent adducts of selones with dihalogens and interhalogens, see: Aragoni et al. (2001 ▶); Boyle & Godfrey (2001 ▶); Roy et al. (2011 ▶).