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

The di-hydro-imidazole ring in the title mol-ecule, C<sub>20</sub>H<sub>20</sub>N<sub>2</sub>O<sub>3</sub>S, is slightly distorted and the lone pair on the tri-coordinate nitro-gen atom is involved in intra-ring π bonding. The methyl-sulfanyl 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 <i>a</i>- and <i>c-</i>axis directions by additional C-H⋯O hydrogen bonds, forming layers parallel to the <i>ac</i> 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.

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Publication Details

Journal
Acta Crystallographica Section E Crystallographic Communications
Published
2024-08-09
DOI
https://doi.org/10.1107/s2056989024007345
Citations
1
Primary Topic
Synthesis of heterocyclic compounds
Type
article
Field-Weighted Citation Impact
0.25

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article

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)

Youssef Ramli, Ahlam I. Al‐Sulami, Basmah H. Allehyani, Abderrazzak El Moutaouakil Ala Allah et al.
1 citations
Acta Crystallographica Section E Crystallographic Communications
Synthesis of heterocyclic compounds
0.25
article

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)

Youssef Ramli, Ahlam I. Al‐Sulami, Basmah H. Allehyani, Abderrazzak El Moutaouakil Ala Allah, Benson M. Kariuki, Joel T. Mague, Abdulsalam Alsubari, Wafa O. Alsulami
article en
1 citations

Abstract

The di-hydro-imidazole ring in the title mol-ecule, C<sub>20</sub>H<sub>20</sub>N<sub>2</sub>O<sub>3</sub>S, is slightly distorted and the lone pair on the tri-coordinate nitro-gen atom is involved in intra-ring π bonding. The methyl-sulfanyl 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 <i>a</i>- and <i>c-</i>axis directions by additional C-H⋯O hydrogen bonds, forming layers parallel to the <i>ac</i> 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.

Acta Crystallographica Section E Crystallographic CommunicationsVol. 80(9)
Tulane University (US), Mohammed V University (MA), University of Jeddah (SA), Cardiff University (GB)
Centre National pour la Recherche Scientifique et Technique
Clean water and sanitation
Openalex Percentile: Top 50%
Synthesis of heterocyclic compounds
0.25
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