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Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-dihydro-1H-benzimidazol-2-one
The title molecule, C(17)H(26)N(2)O, adopts an L-shaped conformation, with the straight n-decyl chain positioned nearly perpendicular to the dihydrobenzimidazole moiety. The dihydrobenzimidazole portion is not quite planar as there is a dihedral angle of 1.20 (6)° between the constituent planes...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8100272/ https://www.ncbi.nlm.nih.gov/pubmed/34026265 http://dx.doi.org/10.1107/S2056989021004291 |
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author | Ait Elmachkouri, Younesse Saber, Asmaa Irrou, Ezaddine Amer, Bushra Mague, Joel T. Hökelek, Tuncer Labd Taha, Mohamed Sebbar, Nada Kheira Essassi, El Mokhtar |
author_facet | Ait Elmachkouri, Younesse Saber, Asmaa Irrou, Ezaddine Amer, Bushra Mague, Joel T. Hökelek, Tuncer Labd Taha, Mohamed Sebbar, Nada Kheira Essassi, El Mokhtar |
author_sort | Ait Elmachkouri, Younesse |
collection | PubMed |
description | The title molecule, C(17)H(26)N(2)O, adopts an L-shaped conformation, with the straight n-decyl chain positioned nearly perpendicular to the dihydrobenzimidazole moiety. The dihydrobenzimidazole portion is not quite planar as there is a dihedral angle of 1.20 (6)° between the constituent planes. In the crystal, N—H⋯O hydrogen bonds form inversion dimers, which are connected into the three-dimensional structure by C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (75.9%), H⋯C/C⋯H (12.5%) and H⋯O/O⋯H (7.0%) interactions. Based on computational chemistry using the CE–B3LYP/6–31 G(d,p) energy model, C—H⋯O hydrogen bond energies are −74.9 (for N—H⋯O) and −42.7 (for C—H⋯O) kJ mol(−1). |
format | Online Article Text |
id | pubmed-8100272 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-81002722021-05-21 Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-dihydro-1H-benzimidazol-2-one Ait Elmachkouri, Younesse Saber, Asmaa Irrou, Ezaddine Amer, Bushra Mague, Joel T. Hökelek, Tuncer Labd Taha, Mohamed Sebbar, Nada Kheira Essassi, El Mokhtar Acta Crystallogr E Crystallogr Commun Research Communications The title molecule, C(17)H(26)N(2)O, adopts an L-shaped conformation, with the straight n-decyl chain positioned nearly perpendicular to the dihydrobenzimidazole moiety. The dihydrobenzimidazole portion is not quite planar as there is a dihedral angle of 1.20 (6)° between the constituent planes. In the crystal, N—H⋯O hydrogen bonds form inversion dimers, which are connected into the three-dimensional structure by C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (75.9%), H⋯C/C⋯H (12.5%) and H⋯O/O⋯H (7.0%) interactions. Based on computational chemistry using the CE–B3LYP/6–31 G(d,p) energy model, C—H⋯O hydrogen bond energies are −74.9 (for N—H⋯O) and −42.7 (for C—H⋯O) kJ mol(−1). International Union of Crystallography 2021-04-27 /pmc/articles/PMC8100272/ /pubmed/34026265 http://dx.doi.org/10.1107/S2056989021004291 Text en © Ait Elmachkouri et al. 2021 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Research Communications Ait Elmachkouri, Younesse Saber, Asmaa Irrou, Ezaddine Amer, Bushra Mague, Joel T. Hökelek, Tuncer Labd Taha, Mohamed Sebbar, Nada Kheira Essassi, El Mokhtar Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-dihydro-1H-benzimidazol-2-one |
title | Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-dihydro-1H-benzimidazol-2-one |
title_full | Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-dihydro-1H-benzimidazol-2-one |
title_fullStr | Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-dihydro-1H-benzimidazol-2-one |
title_full_unstemmed | Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-dihydro-1H-benzimidazol-2-one |
title_short | Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-dihydro-1H-benzimidazol-2-one |
title_sort | crystal structure, hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-dihydro-1h-benzimidazol-2-one |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8100272/ https://www.ncbi.nlm.nih.gov/pubmed/34026265 http://dx.doi.org/10.1107/S2056989021004291 |
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