Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 1-methyl-3-(prop-2-yn-1-yl)-2,3-ainydro-1H-1,3-benzothazol-2-one


Saber A., Srhir M., HÖKELEK T., Mague J. T. , Ahabchane N. H. , Sebbar N. K. , ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.75, pp.1940-1950, 2019 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 75
  • Publication Date: 2019
  • Doi Number: 10.1107/s2056989019015779
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Journal Indexes: Emerging Sources Citation Index, Scopus
  • Page Numbers: pp.1940-1950

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-H-Mthy center dot center dot center dot pi(ring) interactions and C-H-Prop center dot center dot center dot O-Dhyr (Mthy = methyl, Prop = prop-2-yn-1-yl and Dhyr = dihydro) hydrogen bonds form corrugated layers parallel to (10 (1) over bar), which are associated through additional C-H-Bnz center dot center dot center dot O-Dhyr (Bnz = benzene) hydrogen bonds and head-to-tail, slipped, pi-stacking [centroid-to-centroid distance = 3.7712 (7) angstrom] 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 center dot center dot center dot H (44.1%), H center dot center dot center dot C/C center dot center dot center dot H (33.5%) and O center dot center dot center dot H/H center dot center dot center dot 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 center dot center dot center dot O hydrogen-bond energies are 46.8 and 32.5 (for C-H-Prop center dot center dot center dot O-Dhyr) and 20.2 (for C H-Bnz center dot center dot center dot O-Dhyr) 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.