Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazole
In the title molecule, C13H13N3O, the isoxazole ring is inclined to the benzimidazole ring at a dihedral angle of 69.28 (14)°. In the crystal, N—H...N hydrogen bonds between neighboring benzimidazole rings form chains along the a-axis direction. Hirshfeld surface analysis indicates that the most imp...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2021-04-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989021002723 |
| _version_ | 1818490681057869824 |
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| author | Ahlam Idrissi Karim Chkirate Nadeem Abad Bahia Djerrari Redouane Achour El Mokhtar Essassi Luc Van Meervelt |
| author_facet | Ahlam Idrissi Karim Chkirate Nadeem Abad Bahia Djerrari Redouane Achour El Mokhtar Essassi Luc Van Meervelt |
| author_sort | Ahlam Idrissi |
| collection | DOAJ |
| description | In the title molecule, C13H13N3O, the isoxazole ring is inclined to the benzimidazole ring at a dihedral angle of 69.28 (14)°. In the crystal, N—H...N hydrogen bonds between neighboring benzimidazole rings form chains along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (48.8%), H...C/C...H (20.9%) and H...N/N...H (19.3%) interactions. The optimized structure calculated using density functional theory at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gap is 4.9266 eV. |
| first_indexed | 2024-12-10T17:20:13Z |
| format | Article |
| id | doaj.art-257d25c8b114419cb664e1e71313e484 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-10T17:20:13Z |
| publishDate | 2021-04-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-257d25c8b114419cb664e1e71313e4842022-12-22T01:39:59ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902021-04-0177439640110.1107/S2056989021002723tx2037Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazoleAhlam Idrissi0Karim Chkirate1Nadeem Abad2Bahia Djerrari3Redouane Achour4El Mokhtar Essassi5Luc Van Meervelt6Laboratory of Heterocyclic Organic Chemistry URAC 21, Pharmacochemistry Competence Center, Av. Ibn Battouta, BP 1014, Faculty of Sciences, Mohammed V University, Rabat, MoroccoLaboratory of Heterocyclic Organic Chemistry URAC 21, Pharmacochemistry Competence Center, Av. Ibn Battouta, BP 1014, Faculty of Sciences, Mohammed V University, Rabat, MoroccoDepartment of Biochemistry, Faculty of Education & Science, Al-Baydha University, YemenLaboratory of Heterocyclic Organic Chemistry URAC 21, Pharmacochemistry Competence Center, Av. Ibn Battouta, BP 1014, Faculty of Sciences, Mohammed V University, Rabat, MoroccoLaboratory of Heterocyclic Organic Chemistry URAC 21, Pharmacochemistry Competence Center, Av. Ibn Battouta, BP 1014, Faculty of Sciences, Mohammed V University, Rabat, MoroccoLaboratory of Heterocyclic Organic Chemistry URAC 21, Pharmacochemistry Competence Center, Av. Ibn Battouta, BP 1014, Faculty of Sciences, Mohammed V University, Rabat, MoroccoKU Leuven, Chemistry Department, Celestijnenlaan 200F box 2404, Leuven, (Heverlee), B-3001, BelgiumIn the title molecule, C13H13N3O, the isoxazole ring is inclined to the benzimidazole ring at a dihedral angle of 69.28 (14)°. In the crystal, N—H...N hydrogen bonds between neighboring benzimidazole rings form chains along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (48.8%), H...C/C...H (20.9%) and H...N/N...H (19.3%) interactions. The optimized structure calculated using density functional theory at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gap is 4.9266 eV.http://scripts.iucr.org/cgi-bin/paper?S2056989021002723crystal structuredensity functional theorybenzimidazolehydrogen bondhirshfeld surface analysis |
| spellingShingle | Ahlam Idrissi Karim Chkirate Nadeem Abad Bahia Djerrari Redouane Achour El Mokhtar Essassi Luc Van Meervelt Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazole Acta Crystallographica Section E: Crystallographic Communications crystal structure density functional theory benzimidazole hydrogen bond hirshfeld surface analysis |
| title | Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazole |
| title_full | Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazole |
| title_fullStr | Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazole |
| title_full_unstemmed | Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazole |
| title_short | Crystal structure, Hirshfeld surface analysis and density functional theory study of 6-methyl-2-[(5-methylisoxazol-3-yl)methyl]-1H-benzimidazole |
| title_sort | crystal structure hirshfeld surface analysis and density functional theory study of 6 methyl 2 5 methylisoxazol 3 yl methyl 1h benzimidazole |
| topic | crystal structure density functional theory benzimidazole hydrogen bond hirshfeld surface analysis |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989021002723 |
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