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dc.contributor.authorSaber, Asmaa
dc.contributor.authorSrhir, Mohamed
dc.contributor.authorHökelek, Tuncer
dc.contributor.authorMague, Joel T.
dc.contributor.authorHamou Ahabchane, Noureddine
dc.contributor.authorSebbar, Nada Kheira
dc.contributor.authorEssassi, El Mokhtar
dc.date.accessioned2021-06-03T09:15:00Z
dc.date.available2021-06-03T09:15:00Z
dc.date.issued2019
dc.identifier.issn2056-9890
dc.identifier.urihttp://dx.doi.org/10.1107/S2056989019015779
dc.identifier.urihttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC6895944/
dc.identifier.urihttp://hdl.handle.net/11655/24437
dc.description.abstractThe 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—H⋯π(ring) inter­actions and C—H⋯O hydrogen bonds form corrugated layers parallel to (10), which are associated through additional C—H⋯O hydrogen bonds and head-to-tail, slipped, π-stacking inter­actions between di­hydro­benzimidazol-2-one moieties, 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), 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.
dc.language.isoen
dc.relation.isversionof10.1107/S2056989019015779
dc.rightsAttribution 4.0 United States
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.titleCrystal 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
dc.typeinfo:eu-repo/semantics/article
dc.typeinfo:eu-repo/semantics/publishedVersion
dc.relation.journalActa Crystallographica Section E: Crystallographic Communications
dc.contributor.departmentFizik Mühendisliği
dc.identifier.volume75
dc.identifier.issuePt 12
dc.description.indexPubMed
dc.description.indexWoS
dc.description.indexScopus


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Attribution 4.0 United States
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