Analysis of supramolecular self-assembly of two chromene derivatives: Synthesis, crystal structure, Hirshfeld surface, quantum computational and molecular docking studies

Abstract Two 4H-chromene derivatives (1C and 1F) were synthesized by the multicomponent condensation reactions (MCRs) and spectroscopically characterized. The 3-D structures of both the compounds were determined using single crystal X-ray diffraction method. The similar structural conformations are observed in both the compounds but they are stabilized with different packing modes. The supramolecular synthons constructed by strong hydrogen bond interactions plays a major role in the supramolecular self-assembly of molecules in the solid state. Hirshfeld surface analysis is used to assess the various intermolecular interactions in both the structure that driven the self-assembly of molecules in crystal lattices. The propensity of inter-molecular contacts to construct the supramolecular assembly were analyzed using enrichment ratios. The geometrical optimization of both the structures were done by electronic structure method using density functional theory (DFT) to identify the active sites and to explore the chemically reactive parameters of the molecules. Further, novel 1C and 1F compounds were docked with DNA gyrase protein of S. aureus to analyze the binding affinity with targeted protein.