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.
Acta Crystallogr E Crystallogr Commun
; 75(Pt 10): 1411-1417, 2019 Oct 01.
Article
em En
| MEDLINE
| ID: mdl-31636967
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-ylâ¯OCarbx and C-HChlethyâ¯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 Hâ¯H (29.9%), Hâ¯O/Oâ¯H (21.4%), Hâ¯C/C⯠H (19.4%), Hâ¯Cl/Clâ¯H (16.3%) and Câ¯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-ylâ¯OCarbx and C-HChlethyâ¯OCarbx hydrogen bond energies are 67.1 and 61.7â
kJâ
mol-1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6-311â
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.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Acta Crystallogr E Crystallogr Commun
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
Marrocos