Crystallographic structure, quantum and in silico interaction analysis of 3-(benzylthio)-4-hydroxy-2H-chromen-2-one

Abstract

A biologically promising new molecule, 3-(benzylthio)-4-hydroxy-2H-chromen-2-one has been synthesized following visible light-induced protocol in the presence of singlet molecular oxygen. Its detailed spectral properties and X-ray crystal structure are studied. The crystal structure is solved by direct method and refined to a final R value of 0.0701. The crystal structure is stabilized by an elaborate system of hydrogen bonds along with π–π and Van der Waal’s forces to form supramolecular structures. 3D Hirshfeld surfaces and allied 2D fingerprint plots are analyzed for non-covalent interactions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H…H (38.2%) and C···H/H···C (22.4%) interactions. Energy framework analysis allowed us to quantify different contributions to the overall energy. Theoretical (DFT) studies on the molecular structure, Mulliken charges, HOMO, LUMO, MESP surfaces have been performed at B3LYP/6-311 + G(d,p) level of theory. The molecular docking studies are performed to get insights into the inhibition nature of this molecule against CDKS protein and for searching new anticancer agents. Pharmacological analysis was carried out in-order to check the bioactive nature of synthesized compound.