Synthesis and crystal structure analysis of 1-ethyl- 1,3-dihydro-2H-benzo[d]imidazole-2-thion

Abstract

The asymmetric unit of the title compound, C9H10N2S, contains two crystallographically independent, almost planar, molecules. In the crystal, intermolecular N—H⋯S hydrogen bonds link the molecules into pseudocentrosymmetric dimers, enclosing R22(8) ring motifs. There are mutual π–π interactions between the five- and six-membered rings of each independent molecule in the chosen asymmetric unit, with ring centroid-to-centroid distances of 3.6685 (12) and 3.7062 (12) Å. A weak C—H⋯π(ring) interaction is also observed. The N—H⋯S hydrogen bonds, the π–π interactions and the weak C—H⋯π(ring) interaction are effective in the stabilization of the crystal structure. The structure was refined as an inversion twin with a component occupancy ratio of 0.546 (15):0.454 (16).