Abderrazzak El Moutaouakil Ala Allah , Benson M. Kariuki , Abdulsalam Alsubari , Ahlam I. Al-Sulami , Basmah H. Allehyani , Wafa O. Alsulami , Joel T. Mague , Youssef Ramli
{"title":"2-[2-(甲硫基)-5-氧代-4,4-二苯基-4,5-二氢-1H-咪唑-1-基]乙酸乙酯(硫苯妥英衍生物)的合成、晶体结构和 Hirshfeld 表面","authors":"Abderrazzak El Moutaouakil Ala Allah , Benson M. Kariuki , Abdulsalam Alsubari , Ahlam I. Al-Sulami , Basmah H. Allehyani , Wafa O. Alsulami , Joel T. Mague , Youssef Ramli","doi":"10.1107/S2056989024007345","DOIUrl":null,"url":null,"abstract":"<div><p>The dihydroimidazole ring in the title molecule is slightly distorted and the lone pair on the tri-coordinate nitrogen atom is involved in intra-ring π bonding. In the crystal, C—H⋯O hydrogen bonds form inversion dimers, which are connected along the <em>a</em>- and <em>c-</em>axis directions by additional C—H⋯O hydrogen bonds, forming layers parallel to the <em>ac</em> plane.</p></div><div><p>The dihydroimidazole ring in the title molecule, 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 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 <em>a</em>- and <em>c-</em>axis directions by additional C—H⋯O hydrogen bonds, forming layers parallel to the <em>ac</em> 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.</p></div>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"80 9","pages":"Pages 926-930"},"PeriodicalIF":0.5000,"publicationDate":"2024-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"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)\",\"authors\":\"Abderrazzak El Moutaouakil Ala Allah , Benson M. Kariuki , Abdulsalam Alsubari , Ahlam I. Al-Sulami , Basmah H. Allehyani , Wafa O. Alsulami , Joel T. Mague , Youssef Ramli\",\"doi\":\"10.1107/S2056989024007345\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The dihydroimidazole ring in the title molecule is slightly distorted and the lone pair on the tri-coordinate nitrogen atom is involved in intra-ring π bonding. In the crystal, C—H⋯O hydrogen bonds form inversion dimers, which are connected along the <em>a</em>- and <em>c-</em>axis directions by additional C—H⋯O hydrogen bonds, forming layers parallel to the <em>ac</em> plane.</p></div><div><p>The dihydroimidazole ring in the title molecule, 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 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 <em>a</em>- and <em>c-</em>axis directions by additional C—H⋯O hydrogen bonds, forming layers parallel to the <em>ac</em> 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.</p></div>\",\"PeriodicalId\":7367,\"journal\":{\"name\":\"Acta Crystallographica Section E: Crystallographic Communications\",\"volume\":\"80 9\",\"pages\":\"Pages 926-930\"},\"PeriodicalIF\":0.5000,\"publicationDate\":\"2024-09-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Acta Crystallographica Section E: Crystallographic Communications\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2056989024001865\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CRYSTALLOGRAPHY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Crystallographica Section E: Crystallographic Communications","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2056989024001865","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CRYSTALLOGRAPHY","Score":null,"Total":0}
引用次数: 0
摘要
标题分子 C20H20N2O3S 中的二氢咪唑环略微变形,三配位氮原子上的孤对参与了环内 π 键合。甲硫基取代基几乎位于五元环的平面内,而酯类取代基则在该平面外旋转。在晶体中,C-H......O 氢键形成反转二聚体,这些二聚体通过额外的 C-H...O 氢键沿 a 轴和 c 轴方向连接,形成平行于 ac 平面的层。Hirshfeld 表面的主要成分是 C...H/H...C、O...H/H...O 和 S...H/H...S 接触,分别占 20.5%、14.7% 和 4.9%。
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)
The dihydroimidazole ring in the title molecule is slightly distorted and the lone pair on the tri-coordinate nitrogen atom is involved in intra-ring π bonding. 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 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.
期刊介绍:
Acta Crystallographica Section E: Crystallographic Communications is the IUCr''s open-access structural communications journal. It provides a fast, simple and easily accessible publication mechanism for crystal structure determinations of inorganic, metal-organic and organic compounds. The electronic submission, validation, refereeing and publication facilities of the journal ensure rapid and high-quality publication of fully validated structures. The primary article category is Research Communications; these are peer-reviewed articles describing one or more structure determinations with appropriate discussion of the science.