1,3-Benzothiazole-2(3H)-selone

Abstract

The title compound, C7H5NSSe, is the product of the reaction of 2-chlorobenzothiazole with sodium hydroselenide. The molecule is almost planar (r.m.s. deviation = 0.018 Å) owing to the presence of the long chain of conjugated bonds (Se=C—N—C=C—C=C—C=C). The geometrical parameters correspond well to those of the analog N-methylbenzothiazole-2(3H)-selone, demonstrating that the S atom does not take a significant role in the electron delocalization within the molecule. In the crystal, molecules form centrosymmetric dimers by means of intermolecular N—H...Se hydrogen bonds. The dimers have a nonplanar ladder-like structure. Furthermore, the dimers are linked into ribbons propagating in [010] by weak attractive Se...S [3.7593 (4) Å] interactions.