Title of article :
Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-ethoxy-2-oxoethyl)(phenyl)carbamoyl]-2-oxo-1,2-dihydroquinolin-1-yl}acetate
Author/Authors :
Baba,Yassir Filali Laboratoire de Chimie Organique Appliquée - Université Sidi Mohamed Ben Abdallah - Faculté des Sciences et Techniques, Morocco , Hayani, Sonia Laboratoire de Chimie Organique Appliquée - Université Sidi Mohamed Ben Abdallah - Faculté des Sciences et Techniques, Morocco , Hökelek, Tuncer Department of Physics - Hacettepe University, Turkey , Kaur, Manpreet Department of Chemistry - Keene State College, USA , Jasinski, Jerry Department of Chemistry - Keene State College, USA , Sebbar, Nada Kheira Laboratoire de Chimie bioorganique appliquée - Faculté des sciences, Morocco , Kandri Rodi, Youssef Laboratoire de Chimie Organique Appliquée - Université Sidi Mohamed Ben Abdallah - Faculté des Sciences et Techniques, Morocco
Abstract :
The title compound, C24H24N2O6, consists of ethyl 2-(1,2,3,4-tetrahydro-2-oxoquinolin-1-yl)acetate and 4-[(2-ethoxy-2-oxoethyl)(phenyl)carbomoyl] units, where the oxoquinoline unit is almost planar and the acetate substituent is nearly perpendicular to its mean plane. In the crystal, C—HOxqn⋯OEthx and C—HPhyl⋯OCarbx (Oxqn = oxoquinolin, Ethx = ethoxy, Phyl = phenyl and Carbx = carboxylate) weak hydrogen bonds link the molecules into a three-dimensional network sturucture. A π–π interaction between the constituent rings of the oxoquinoline 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%) interactions. Weak intermolecular hydrogen-bond interactions and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) geometric optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO molecular orbital behaviour was elucidated to determine the energy gap.
Keywords :
Hirshfeld surface , Hirshfeld surface , π-stacking , weak intermolecular interactions , alkyne , 2-oxoquinoline , crystal structure
Journal title :
Acta Crystallographica Section E: Crystallographic Communications