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

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Gurbanov A. V., Guseinov F. I., Samigullina A. I., HÖKELEK T., Hasanov K. I., Javadzade T. A., ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, pp.169-176, 2025 (ESCI)

• Publication Type: Article / Article
• Publication Date: 2025
• Doi Number: 10.1107/s2056989025000519
• Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
• Journal Indexes: Emerging Sources Citation Index (ESCI)
• Page Numbers: pp.169-176
• Open Archive Collection: AVESIS Open Access Collection
• Hacettepe University Affiliated: Yes

Abstract

The asymmetric unit of the title compound, C9H10N2S, contains two crystallographically independent, almost planar, molecules. In the crystal, intermolecular N-H center dot center dot center dot S hydrogen bonds link the molecules into pseudocentrosymmetric dimers, enclosing R-2(2)(8) ring motifs. There are mutual pi-pi 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) angstrom degrees. A weak C-H center dot center dot center dot pi (ring) interaction is also observed. The N-H center dot center dot center dot S hydrogen bonds, the pi-pi interactions and the weak C-H center dot center dot center dot pi (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).