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


Baba Y. F. , HÖKELEK T. , Kaur M., Jasinski J., Sebbar N. K. , Rodi Y. K.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.75, pp.1753-1765, 2019 (Journal Indexed in ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 75
  • Publication Date: 2019
  • Doi Number: 10.1107/s2056989019014154
  • Title of Journal : ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Page Numbers: pp.1753-1765

Abstract

The title compound, C24H24N2O6, consists of ethyl 2-(1,2,3,4-tetrahydro-2-oxo-quinolin-l-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-H-oxqn center dot center dot center dot O-Ethx and C-HPhyl center dot center dot center dot O-Carbx ( Oxqn = oxoquinolin, Ethx = ethoxy, Phyl = phenyl and Carbx = carboxylate) weak hydrogen bonds link the molecules into a threedimensional network sturucture. A pi-pi interaction between the constituent rings of the oxoquinoline unit, with a centroid-centroid distance of 3.675 (1) angstrom 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 center dot center dot center dot H (53.9%), H center dot center dot center dot O/O center dot center dot center dot H (28.5%) and H center dot center dot center dot C/C center dot center dot center dot 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.