Noncovalent interaction analysis and bioactivity evaluation of a novel chlorinated Schiff compound

Intermolecular interactions play a significant role in the area of pharmaceuticals. Hence, there is an
increasing trend towards the analysis of noncovalent interactions of active molecules to investigate
the correlation between structure and properties. In this context, new Schiff base compound 2,4-
dichloro-6-(((4-chlorobenzyl)imino)methyl)phenol has been prepared by condensation of 3,5-dichloro-2-
hydroxybenzaldehyde and (4-chlorobenzyl)methenamine. The single crystals of Schiff base were
obtained by the slow evaporation method. To investigate the solid-state behaviour and noncovalent
interactions, X-ray diffraction analysis was performed. The crystal packing pattern is evident that non-
covalent C–H‧‧‧O, C–H‧‧‧p and p‧‧‧p interactions result in 2-D supramolecular architecture.
Meanwhile, computational studies were carried out to rationalize the strength and nature of different
types of interactions involved in the crystal packing. Hirshfeld surface and enrichment ratio analyses
provide the quantitative contribution of each intermolecular interaction. The intramolecular hydrogen
bonding environment is well supported qualitatively by QTAIM and NCI isosurface. Based on the opti-
mized ground state geometry by density functional theory, the physical and chemical properties of
the compound were investigated. To acquire a more profound comprehension of the interaction of
the ligand with the protein and their binding affinity, in-silico docking and molecular dynamic simula-
tion studies were performed. It has also been observed that the Schiff base compound unveiled anti-
bacterial activity against the bacterial species MRSA.