Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one
In the title molecule, C11H10N2O, the dihydrobenzimidazol-2-one moiety is essentially planar, with the prop-2-yn-1-yl substituent rotated well out of this plane. In the crystal, C—HMthy...π(ring) interactions and C—HProp...ODhyr (Mthy = methyl, Prop = prop-2-yn-1-yl and Dhyr = dihydro) hydrogen bond...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019-12-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019015779 |
| _version_ | 1819289447808630784 |
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| author | Asmaa Saber Mohamed Srhir Tuncer Hökelek Joel T. Mague Noureddine Hamou Ahabchane Nada Kheira Sebbar El Mokhtar Essassi |
| author_facet | Asmaa Saber Mohamed Srhir Tuncer Hökelek Joel T. Mague Noureddine Hamou Ahabchane Nada Kheira Sebbar El Mokhtar Essassi |
| author_sort | Asmaa Saber |
| collection | DOAJ |
| description | In the title molecule, C11H10N2O, the dihydrobenzimidazol-2-one moiety is essentially planar, with the prop-2-yn-1-yl substituent rotated well out of this plane. In the crystal, C—HMthy...π(ring) interactions and C—HProp...ODhyr (Mthy = methyl, Prop = prop-2-yn-1-yl and Dhyr = dihydro) hydrogen bonds form corrugated layers parallel to (10\overline{1}), which are associated through additional C—HBnz...ODhyr (Bnz = benzene) hydrogen bonds and head-to-tail, slipped, π-stacking [centroid-to-centroid distance = 3.7712 (7) Å] interactions between dihydrobenzimidazol-2-one moieties. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (44.1%), H...C/C...H (33.5%) and O...H/H...O (13.4%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry calculations indicate that in the crystal, C—H...O hydrogen-bond energies are 46.8 and 32.5 (for C—HProp...ODhyr) and 20.2 (for C—HBnz...ODhyr) kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap. |
| first_indexed | 2024-12-24T03:07:00Z |
| format | Article |
| id | doaj.art-e16c258ee96e48f3836b20825722e532 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-24T03:07:00Z |
| publishDate | 2019-12-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-e16c258ee96e48f3836b20825722e5322022-12-21T17:17:58ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-12-0175121940194610.1107/S2056989019015779lh5936Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-oneAsmaa Saber0Mohamed Srhir1Tuncer Hökelek2Joel T. Mague3Noureddine Hamou Ahabchane4Nada Kheira Sebbar5El Mokhtar Essassi6Laboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, MoroccoLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, MoroccoDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, TurkeyDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USALaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, MoroccoLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, MoroccoLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, MoroccoIn the title molecule, C11H10N2O, the dihydrobenzimidazol-2-one moiety is essentially planar, with the prop-2-yn-1-yl substituent rotated well out of this plane. In the crystal, C—HMthy...π(ring) interactions and C—HProp...ODhyr (Mthy = methyl, Prop = prop-2-yn-1-yl and Dhyr = dihydro) hydrogen bonds form corrugated layers parallel to (10\overline{1}), which are associated through additional C—HBnz...ODhyr (Bnz = benzene) hydrogen bonds and head-to-tail, slipped, π-stacking [centroid-to-centroid distance = 3.7712 (7) Å] interactions between dihydrobenzimidazol-2-one moieties. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (44.1%), H...C/C...H (33.5%) and O...H/H...O (13.4%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry calculations indicate that in the crystal, C—H...O hydrogen-bond energies are 46.8 and 32.5 (for C—HProp...ODhyr) and 20.2 (for C—HBnz...ODhyr) kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.http://scripts.iucr.org/cgi-bin/paper?S2056989019015779crystal structurebenzimidazol-2-onehydrogen bondc—h...π(ring) interactionπ-stackinghirshfeld surface |
| spellingShingle | Asmaa Saber Mohamed Srhir Tuncer Hökelek Joel T. Mague Noureddine Hamou Ahabchane Nada Kheira Sebbar El Mokhtar Essassi Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one Acta Crystallographica Section E: Crystallographic Communications crystal structure benzimidazol-2-one hydrogen bond c—h...π(ring) interaction π-stacking hirshfeld surface |
| title | Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one |
| title_full | Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one |
| title_fullStr | Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one |
| title_full_unstemmed | Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one |
| title_short | Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one |
| title_sort | crystal structure hirshfeld surface analysis and interaction energy and dft studies of 1 methyl 3 prop 2 yn 1 yl 2 3 dihydro 1h 1 3 benzodiazol 2 one |
| topic | crystal structure benzimidazol-2-one hydrogen bond c—h...π(ring) interaction π-stacking hirshfeld surface |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019015779 |
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