Synthesis, crystal structure and Hirshfeld surface analysis of 5,5-diphenyl-3-(prop-2-yn-1-yl)imidazolidine-2,4-dione
The new phenytoin analogue 5,5-diphenyl-3-(2-propyn-1-yl)imidazolidine-2,4-dione, C18H14N2O2 (3), was obtained through an alkylation reaction with propargyl bromide via the phase-transfer catalysis method, and its structure was determined via single-crystal X-ray diffraction analysis. The asymmetric...
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International Union of Crystallography
2025-05-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | https://journals.iucr.org/paper?S2056989025003391 |
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| author | Abderrazzak El Moutaouakil Ala Allah Chiara Massera Walid Guerrab Abdulsalam Alsubari Joel T. Mague Youssef Ramli |
| author_facet | Abderrazzak El Moutaouakil Ala Allah Chiara Massera Walid Guerrab Abdulsalam Alsubari Joel T. Mague Youssef Ramli |
| author_sort | Abderrazzak El Moutaouakil Ala Allah |
| collection | DOAJ |
| description | The new phenytoin analogue 5,5-diphenyl-3-(2-propyn-1-yl)imidazolidine-2,4-dione, C18H14N2O2 (3), was obtained through an alkylation reaction with propargyl bromide via the phase-transfer catalysis method, and its structure was determined via single-crystal X-ray diffraction analysis. The asymmetric unit of 3 consists of two independent molecules differing mainly in the orientation of the propynyl group. Each molecule forms an inversion dimer through pairs of N2—H2...O2 hydrogen bonds. The crystal structure is further consolidated by C—H...O and C—H...π interactions. The contributions of the different interactions towards the crystal packing were further analysed using Hirshfeld surface and fingerprint plots, showing that the largest contribution comes from the H...H contacts (45%). |
| format | Article |
| id | doaj-art-5bbc8bdca9fa477daa323e017b8b514c |
| institution | DOAJ |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-5bbc8bdca9fa477daa323e017b8b514c2025-08-20T03:11:30ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-05-0181541241610.1107/S2056989025003391vm2311Synthesis, crystal structure and Hirshfeld surface analysis of 5,5-diphenyl-3-(prop-2-yn-1-yl)imidazolidine-2,4-dioneAbderrazzak El Moutaouakil Ala Allah0Chiara Massera1Walid Guerrab2Abdulsalam Alsubari3Joel T. Mague4Youssef Ramli5Laboratory of Medicinal Chemistry, Drug Sciences Research Center, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, MoroccoDipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Università di Parma, Parco Area delle Scienze 17/A 43124 Parma, ItalyLaboratory of Medicinal Chemistry, Drug Sciences Research Center, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, MoroccoLaboratory of Medicinal Chemistry, Faculty of Clinical Pharmacy, 21 September University, YemenDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USALaboratory of Medicinal Chemistry, Drug Sciences Research Center, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, MoroccoThe new phenytoin analogue 5,5-diphenyl-3-(2-propyn-1-yl)imidazolidine-2,4-dione, C18H14N2O2 (3), was obtained through an alkylation reaction with propargyl bromide via the phase-transfer catalysis method, and its structure was determined via single-crystal X-ray diffraction analysis. The asymmetric unit of 3 consists of two independent molecules differing mainly in the orientation of the propynyl group. Each molecule forms an inversion dimer through pairs of N2—H2...O2 hydrogen bonds. The crystal structure is further consolidated by C—H...O and C—H...π interactions. The contributions of the different interactions towards the crystal packing were further analysed using Hirshfeld surface and fingerprint plots, showing that the largest contribution comes from the H...H contacts (45%).https://journals.iucr.org/paper?S2056989025003391crystal structurehydantoinalkylationhirshfeld surface analysis |
| spellingShingle | Abderrazzak El Moutaouakil Ala Allah Chiara Massera Walid Guerrab Abdulsalam Alsubari Joel T. Mague Youssef Ramli Synthesis, crystal structure and Hirshfeld surface analysis of 5,5-diphenyl-3-(prop-2-yn-1-yl)imidazolidine-2,4-dione Acta Crystallographica Section E: Crystallographic Communications crystal structure hydantoin alkylation hirshfeld surface analysis |
| title | Synthesis, crystal structure and Hirshfeld surface analysis of 5,5-diphenyl-3-(prop-2-yn-1-yl)imidazolidine-2,4-dione |
| title_full | Synthesis, crystal structure and Hirshfeld surface analysis of 5,5-diphenyl-3-(prop-2-yn-1-yl)imidazolidine-2,4-dione |
| title_fullStr | Synthesis, crystal structure and Hirshfeld surface analysis of 5,5-diphenyl-3-(prop-2-yn-1-yl)imidazolidine-2,4-dione |
| title_full_unstemmed | Synthesis, crystal structure and Hirshfeld surface analysis of 5,5-diphenyl-3-(prop-2-yn-1-yl)imidazolidine-2,4-dione |
| title_short | Synthesis, crystal structure and Hirshfeld surface analysis of 5,5-diphenyl-3-(prop-2-yn-1-yl)imidazolidine-2,4-dione |
| title_sort | synthesis crystal structure and hirshfeld surface analysis of 5 5 diphenyl 3 prop 2 yn 1 yl imidazolidine 2 4 dione |
| topic | crystal structure hydantoin alkylation hirshfeld surface analysis |
| url | https://journals.iucr.org/paper?S2056989025003391 |
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