Study of supramolecular self-assembly of pyridone and dihydropyridone co-crystal: Synthesis, crystal structure, Hirshfeld surface, DFT and molecular docking studies

Abstract

Dihydropyridone is synthesized by the multicomponent condensation reactions (MCRs), followed by three different oxidation methods to synthesize pyridone. The 3-D self-assemblies of both the compounds were determined using the single-crystal X-ray diffraction method. Dihydropyridone products are found as a racemic mixture in synthesis and crystalized as co-crystal. Similar structural conformations are observed in both the compounds but stabilized with different non-covalent interactions. Hirshfeld surface analysis is done to analyze the various intermolecular interactions in both the structure. This study gives the clue of driving force in the self-assembly of molecules in crystal lattices. The propensity of inter-molecular contacts to construct the supramolecular assembly was further studied using DFT. The geometrical optimizations of both the compounds were done by the electronic structure method using density functional theory (DFT) to identify the active sites and explore the molecules' chemically reactive parameters. Further, both compounds were docked with Survivin Protein and Kinesin Eg5 protein to analyze the binding affinity with targeted protein.