Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 2-chloro-ethyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-di-hydro-quinoline-4-carboxyl-ate.

ABSTRACT: The title compound, C15H12ClNO3, consists of a 1,2-di-hydro-quinoline-4-carb-oxyl-ate unit with 2-chloro-ethyl and propynyl substituents, where the quinoline moiety is almost planar and the propynyl substituent is nearly perpendicular to its mean plane. In the crystal, the mol-ecules form zigzag stacks along the a-axis direction through slightly offset ?-stacking inter-actions between inversion-related quinoline moieties which are tied together by inter-molecular C-HPrpn-yl?OCarbx and C-HChlethy?OCarbx (Prpnyl = propynyl, Carbx = carboxyl-ate and Chlethy = chloro-eth-yl) hydrogen bonds. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?H (29.9%), H?O/O?H (21.4%), H?C/C? H (19.4%), H?Cl/Cl?H (16.3%) and C?C (8.6%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HPrpn-yl?OCarbx and C-HChlethy?OCarbx hydrogen bond energies are 67.1 and 61.7?kJ?mol-1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6-311?G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

SUBMITTER: Hayani S 

PROVIDER: S-EPMC6775731 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature