Abstract
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.
Funder
National Science Foundation
Tulane University
Hacettepe Üniversitesi
Publisher
International Union of Crystallography (IUCr)
Subject
Condensed Matter Physics,General Materials Science,General Chemistry