Influence of hydroxyl group in stabilizing the Schiff base crystal structure: Crystal structure, computational and molecular docking studies

To investigate the synergetic effect in the formation of crystal structure having two independent molecules in the asymmetric unit and the structure-property relationship of the molecule, we have synthesized the Schiff base compound (E)-4-(((4-chlorobenzyl)imino)methyl)benzene-1,2,3-triol. The for-mation of the desired compound was confirmed by the FTIR and single-crystal X-ray studies. The en-riched hydroxyl group exhibits more intra and inter-strong hydrogen bonds. The chlorine-hydrogen and C6-H6 middotmiddotmiddot pi interaction along with other interactions form a supramolecular architecture. The Hirshfeld surface analysis and 2D fingerprint analysis provide valuable information about the intermolecular inter-action present in the crystal structure. The likelihood of occurrence of intermolecular contacts present in the crystal structure was analyzed using enrichment ratio. The visualization of the interaction topology along with interaction energy between the molecules are carried out using an energy framework. QTAIM, NCI, ELF and LOL studies provide information about electron charge density distribution and the nature of intramolecular and dimeric interaction. The DFT studies provide ground state energy of the optimized structure and the HOMO-LUMO energy gap. The molecular electrostatic potential provides the reactive site and anisotropy of charge distribution of chlorine atom. The NBO studies provide stabilization en-ergy associated with the delocalization of orbitals. The docking studies were also carried out for SARS COVID-19 and the effect of hydroxyl group substitution on binding interaction was investigated.(c) 2023 Elsevier B.V. All rights reserved.