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

Abstract

Mol­ecules of 1-ethyl-1,3-di­hydro-2H-benzo[d]imidazole-2-thione are almost planar. In the crystal, inter­molecular N—H⋯S hydrogen bonds link the mol­ecules into pseudocentrosymmetric dimers. N—H⋯S hydrogen bonds, π–π inter­actions and a weak C—H⋯π(ring) inter­action are effective in the stabilization of the crystal structure.

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).