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

• Main Authors: Sevgi Kansiz, Digdem Tatlidil, Necmi Dege, Feyzi Alkim Aktas, Samir Osman Mohammed Al-Asbahy, Aysen Alaman Agar
• Format: Article
• Language: English
• Published: International Union of Crystallography 2021-06-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; schiff base; diphenylethan; molecular docking; covid-19 main protease
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989021005442

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.