Novel supramolecular co-crystal of 8-hydroxyquinoline with acetone-(2,4-dinitrophenyl)hydrazone: One pot synthesis, structural characterization, Hirshfeld surface and energy framework analysis, computational investigation and molecular docking study

Inspired by Betti reaction, a novel co-crystal of 8-hydroxyquinoline with acetone-(2,4-dinitrophenyl) hydrazone (I) was isolated in a one-pot 3 component assembly by reacting 8-hydroxyquinoline (8-HQ) with 2,4-dinitrohydrazine (DNPH) and formaldehyde. The crystal structure of (I) was characterized by single crystal X-ray diffraction analysis which shows that the hydrogen bonding and pi-pi stacking are the main driving forces for the co-crystal building. The topology of the intermolecular interaction energies in the crystal packing was analyzed and exposed using 3D energy framework analysis. The calculations of the studied molecule at the B3LYP levels in the 3-21g, 6-31g and 6-31++g** basis sets were made using the Gaussian package program. Theoretical calculations were executed to develop optimized geometry, frontier molecular orbital analysis and the NLO properties of the considered molecule, Furthermore, Molecular docking calculations were made. Afterwards, the interactions occurring in the docking calculation against the anti-oxidant protein (ID: 1HD2, 3NRZ, 4Z8D) were examined in detail with Schro center dot dinger maestro.