Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-eth-oxy-2-oxoeth-yl)(phen-yl)carbamo-yl]-2-oxo-1,2-di-hydro-quinolin-1-yl}acetate.

Academic Journal

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.
Hayani S; 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.
Kaur M; Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA.
Jasinski J; Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA.
Sebbar NK; Laboratoire de Chimie bioorganique appliquée, Faculté des sciences, Université Ibn Zohr, Agadir, Morocco.; Laboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, 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 Oct 29; Vol. 75 (Pt 11), pp. 1753-1758. Date of Electronic Publication: 2019 Oct 29 (Print Publication: 2019).

English

The title com-pound, C 24 H 24 N 2 O 6 , consists of ethyl 2-(1,2,3,4-tetra-hydro-2-oxo-quinolin-1-yl)acetate and 4-[(2-eth-oxy-2-oxoeth-yl)(phen-yl)carbomoyl] units, where the oxo-quinoline unit is almost planar and the acetate substituent is nearly perpendicular to its mean plane. In the crystal, C-H Oxqn ⋯O Ethx and C-H Ph-yl ⋯O Carbx (Oxqn = oxoquinolin, Ethx = eth-oxy, Phyl = phenyl and Carbx = carboxyl-ate) weak hydrogen bonds link the mol-ecules into a three-dimensional network sturucture. A π-π inter-action between the constituent rings of the oxo-quinoline unit, with a centroid-centroid distance of 3.675 (1) Å may further stabilize the structure. Both terminal ethyl groups are disordered over two sets of sites. The ratios of the refined occupanies are 0.821 (8):0.179 (8) and 0.651 (18):0.349 (18). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (53.9%), H⋯O/O⋯H (28.5%) and H⋯C/C⋯H (11.8%) inter-actions. Weak inter-molecular hydrogen-bond inter-actions and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Density functional theory (DFT) geometric optimized structures at the B3LYP/6-311G(d,p) level are com-pared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO mol-ecular orbital behaviour was elucidated to determine the energy gap.
(© Filali Baba et al. 2019.)