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2-[2-(甲基硫烷基)-5-氧代-4,4-二苯基-4,5-二氢-1-咪唑-1-基]乙酸乙酯(硫代苯妥英衍生物)的合成、晶体结构及 Hirshfeld 表面

Synthesis, crystal structure and Hirshfeld surface of ethyl 2-[2-(methyl-sulfan-yl)-5-oxo-4,4-diphenyl-4,5-di-hydro-1-imidazol-1-yl]acetate (thio-phenytoin derivative).

作者信息

El Moutaouakil Ala Allah Abderrazzak, Kariuki Benson M, Alsubari Abdulsalam, Al-Sulami Ahlam I, Allehyani Basmah H, Alsulami Wafa O, Mague Joel T, Ramli Youssef

机构信息

Laboratory of Medicinal Chemistry Drug Sciences Research Center Faculty of Medicine and Pharmacy Mohammed V University in Rabat Morocco.

School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, United Kingdom.

出版信息

Acta Crystallogr E Crystallogr Commun. 2024 Aug 9;80(Pt 9):926-930. doi: 10.1107/S2056989024007345. eCollection 2024 Sep 1.

Abstract

The di-hydro-imidazole ring in the title mol-ecule, CHNOS, 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 - and axis directions by additional C-H⋯O hydrogen bonds, forming layers parallel to the 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.

摘要

标题分子CHNOS中的二氢咪唑环略有扭曲,三配位氮原子上的孤对电子参与了环内π键合。甲硫基取代基几乎位于五元环平面内,而酯基取代基则旋转至该平面之外。在晶体中,C-H⋯O氢键形成反演二聚体,这些二聚体通过额外的C-H⋯O氢键沿 - 和轴方向相连,形成平行于 平面的层。Hirshfeld表面的主要贡献者分别是C⋯H/H⋯C、O⋯H/H⋯O和S⋯H/H⋯S接触,占比分别为20.5%、14.7%和4.9%。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bec0/11389683/647517689d79/e-80-00926-fig1.jpg

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