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.

Academic Journal

Hayani S; Laboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202, Fez, Morocco.
Filali Baba Y; Laboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202, Fez, Morocco.
Hökelek T; Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey.
Ouazzani Chahdi F; Laboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202, Fez, Morocco.
Mague JT; Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
Sebbar NK; Laboratoire de Chimie Bioorganique Appliquée, Faculté des Sciences, Université Ibn Zohr, Agadir, Morocco.
Kandri Rodi Y; Laboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202, Fez, Morocco.

Acta crystallographica. Section E, Crystallographic communications [Acta Crystallogr E Crystallogr Commun] 2019 Sep 06; Vol. 75 (Pt 10), pp. 1411-1417. Date of Electronic Publication: 2019 Sep 06 (Print Publication: 2019).

English

The title compound, C 15 H 12 ClNO 3 , 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-H Prpn-yl ⋯O Carbx and C-H Chlethy ⋯O Carbx (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-H Prpn-yl ⋯O Carbx and C-H Chlethy ⋯O Carbx 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.
(© Hayani et al. 2019.)