Crystal structure and molecular docking study of (E)-2-{[(E)-2-hydroxy-5-methylbenzylidene]hydrazinylidene}-1,2-diphenylethan-1-one

Abstract

The title compound, C22H18N2O2, is a Schiff base that exists in the phenol–imine tautomeric form and adopts an E configuration with respect to the C=N bond. The molecular structure is stabilized by an O—H...N hydrogen bond, forming an S(6) ring motif. In the crystal, pairs of C—H...O hydrogen bonds link the molecules to form inversion dimers. Weak π–π stacking interactions along the a-axis direction provide additional stabilization of the crystal structure. The molecule is non-planar, the aromatic ring of the benzaldehyde residue being nearly perpendicular to the phenyl and 4-methylphenol rings with dihedral angles of 88.78 (13) and 82.26 (14)°, respectively. A molecular docking study between the title molecule and the COVID-19 main protease (PDB ID: 6LU7) was performed, showing that it is a potential agent because of its affinity and ability to adhere to the active sites of the protein.

Keywords

• crystal structure
• schiff base
• diphenylethan
• molecular docking
• covid-19 main protease