Acta Crystallographica Section E: Crystallographic Communications (Aug 2021)

Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylate

  • Younos Bouzian,
  • Karim Chkirate,
  • Joel T. Mague,
  • Fares Hezam Al-Ostoot,
  • Noureddine Hammou Ahabchane,
  • El Mokhtar Essassi

Journal volume & issue
Vol. 77, no. 8
pp. 824 – 828


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The title molecule, C20H15NO3, adopts a Z-shaped conformation with the carboxyl group nearly coplanar with the dihydroquinoline unit. In the crystal, corrugated layers are formed by C—H...O hydrogen bonds and are stacked by C—H...π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (43.3%), H...C/C...H (26.6%) and H...O/O...H (16.3%) interactions. The optimized structure calculated using density functional theory at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 4.0319 eV.