Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate

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

doi:10.1107/S2056989021007416

Crystal structure, Hirshfeld surface analysis and density functional theory study of benzyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate

Acta Crystallogr E Crystallogr Commun. 2021 Jul 23;77(Pt 8):824-828. doi: 10.1107/S2056989021007416. eCollection 2021 Aug 1.

Authors

Younos Bouzian¹, Karim Chkirate¹, Joel T Mague², Fares Hezam Al-Ostoot³, Noureddine Hammou Ahabchane¹, El Mokhtar Essassi¹

Affiliations

¹ Laboratory of Heterocyclic Organic Chemistry URAC 21, Pharmacochemistry Competence Center, Av. Ibn Battouta, BP 1014, Faculty of Sciences, Mohammed V University, Rabat, Morocco.
² Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
³ Department of Biochemistry, Faculty of Education & Science, Al-Baydha University, Yemen.

Abstract

The title mol-ecule, C₂₀H₁₅NO₃, adopts a Z-shaped conformation with the carboxyl group nearly coplanar with the di-hydro-quinoline unit. In the crystal, corrugated layers are formed by C-H⋯O hydrogen bonds and are stacked by C-H⋯π(ring) inter-actions. 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%) inter-actions. 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.

Keywords: Hirshfeld surface analysis; alkyne; crystal structure; dihydroquinoline; hydrogen bond.