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

Acta Crystallographica Section E: Crystallographic Communications

Jerry Jasinski¹  Manpreet Kaur¹  Tuncer Hökelek²  Youssef Kandri Rodi³  Yassir Filali Baba³  Sonia Hayani³  Nada Kheira Sebbar⁴ 

[1] Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA;Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey;Laboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'immouzzer, BP 2202, Fez, Morocco;Laboratoire de Chimie bioorganique appliquée, Faculté des sciences, Université Ibn Zohr, Agadir, Morocco;

关键词: crystal structure;    2-oxoquinoline;    alkyne;    weak intermolecular interactions;    π-stacking;    hirshfeld surface;   

DOI  :  10.1107/S2056989019014154

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown