Synthesis, crystal structure and Hirshfeld surface of ethyl 2-[2-(methylsulfanyl)-5-oxo-4,4-diphenyl-4,5-dihydro-1H-imidazol-1-yl]acetate (thiophenytoin derivative)

El Moutaouakil Ala Allah, Abderrazzak, Kariuki, Benson M. ORCID: https://orcid.org/0000-0002-8658-3897, Alsubari, Abdulsalam, Al-Sulami, Ahlam I., Allehyani, Basmah H., Alsulami, Wafa O., Mague, Joel T. and Ramli, Youssef 2024. Synthesis, crystal structure and Hirshfeld surface of ethyl 2-[2-(methylsulfanyl)-5-oxo-4,4-diphenyl-4,5-dihydro-1H-imidazol-1-yl]acetate (thiophenytoin derivative). Acta Crystallographica Section E: Crystallographic Communications 80 (9) , pp. 926-930. 10.1107/S2056989024007345

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Abstract

The di­hydro­imidazole ring in the title mol­ecule, C20H20N2O3S, is slightly distorted and the lone pair on the tri-coordinate nitro­gen atom is involved in intra-ring π bonding. The methyl­sulfanyl substituent lies nearly in the plane of the five-membered ring while the ester substituent is rotated well out of that plane. In the crystal, C—H⋯O hydrogen bonds form inversion dimers, which are connected along the a- and c-axis directions by additional C—H⋯O hydrogen bonds, forming layers parallel to the ac plane. The major contributors to the Hirshfeld surface are C⋯H/H⋯C, O⋯H/H⋯O and S⋯H/H⋯S contacts at 20.5%, 14.7% and 4.9%, respectively.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	International Union of Crystallography
ISSN:	2056-9890
Date of First Compliant Deposit:	3 October 2024
Date of Acceptance:	23 July 2024
Last Modified:	07 Oct 2024 10:45
URI:	https://orca.cardiff.ac.uk/id/eprint/172568

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