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.

Sonia Hayani,Youssef Kandri Rodi,Nada Kheira Sebbar,Tuncer Hökelek,Fouad Ouazzani Chahdi,Yassir Filali Baba,Joel T Mague

doi:10.1107/s2056989019012283

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 π-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.

Highlights

Sonia Hayani,a* Yassir Filali Baba,a Tuncer Hokelek,b Fouad Ouazzani Chahdi,a Joel T
The title compound, C15H12ClNO3, consists of a 1,2-dihydroquinoline-4carboxylate unit with 2-chloroethyl and propynyl substituents, where the quinoline moiety is almost planar and the propynyl substituent is nearly perpendicular to its mean plane
The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from HÁ Á ÁH (29.9%), HÁ Á ÁO/OÁ Á ÁH (21.4%), HÁ Á ÁC/ CÁ Á Á H (19.4%), HÁ Á ÁCl/ClÁ Á ÁH (16.3%) and CÁ Á ÁC (8.6%) interactions

Summary

Chemical context

The quinoline ring system is an important structural unit in naturally occurring quinoline alkaloids, therapeutics and synthetic analogues with interesting biological activities. Substituted quinolines have been reported to act as antagonists for endothelin (Cheng et al, 1996), 5HT3 (Anzini et al, 1995), NK-3 (Giardina et al, 1997) and leukotriene D4 (Gauthier et al, 1990) receptors. They are used as inhibitors of gastric (H+/K+)-ATPase (Ife et al, 1992), dihydroorotate dehydrogenase (Chen et al, 1990) and 5-lipoxygenase (Musser et al, 1987). Angle of 47.13 (23); this is indicated by the C1—C9— C13—O2 torsion angle of À44.2 (6)

Supramolecular features

Structural commentary

Hirshfeld surface analysis

Interaction energy calculations

Findings

DFT calculations