Crystal structure, Hirshfeld surface analysis, DFT and mol-ecular docking investigation of 2-(2-oxo-1,3-oxazolidin-3-yl)ethyl 2-[2-(2-oxo-1,3-oxazolidin-3-yl)eth-oxy]quinoline-4-carboxyl-ate

Acta Crystallogr E Crystallogr Commun. 2021 Jan 1;77(Pt 1):28-33. doi: 10.1107/S2056989020015960.

Abstract

In the mol-ecular structure of the title compound, C20H21N3O7, the quinoline ring system is slightly bent, with a dihedral angle between the phenyl and the pyridine rings of 3.47 (7)°. In the crystal, corrugated layers of mol-ecules extending along the ab plane are generated by C-H⋯O hydrogen bonds. The inter-molecular inter-actions were qu-anti-fied by Hirshfeld surface analysis and two-dimensional fingerprint plots. The most significant contributions to the crystal packing are from H⋯H (42.3%), H⋯O/O⋯H (34.5%) and H⋯C/ C⋯H (17.6%) contacts. Mol-ecular orbital calculations providing electron-density plots of the HOMO and LUMO as well as mol-ecular electrostatic potentials (MEP) were computed, both with the DFT/B3LYP/6-311 G++(d,p) basis set. A mol-ecular docking study between the title mol-ecule and the COVID-19 main protease (PDB ID: 6LU7) was performed, showing that it is a good agent because of its affinity and ability to adhere to the active sites of the protein.

Keywords: Covid-19; DFT; Hirshfeld surface analysis; Mol­ecular docking; crystal structure; oxazolidine; quinoline.

Grants and funding

This work was funded by National Science Foundation grant 1228232. Tulane University grant .