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)

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.

Keywords

• crystal structure
• thiophenytoin
• dihydroimidazole
• hydrogen bond
• ester
• thioether