Synthesis, structural, spectroscopic (NMR, FT-IR and UV-Vis), NLO, in silico (ADMET and molecular docking) and DFT investigations of a flavonol derivative 2-(4-chlorophenyl)-7-fluoro-3-hydroxy-4H-chromen-4-one

The geometric, spectroscopic and electronic features of the newly synthesized 3-Hydroxy-2-(4-chlorophenyl)-7fluoro-4H-chromen-4-one have been analyzed using a combination of single crystal XRD, FT-IR, NMR shifts, and UV-Vis. spectroscopic methods both experimentally and theoretically. The molecule has crystallized in orthorhombic space group Pca21 and it has stabilized with C-H & sdot;& sdot;& sdot;O, O-H & sdot;& sdot;& sdot;O intra-molecular and O-H & sdot;& sdot;& sdot;O intermolecular interactions. The geometric parameters (bond lengths and bond angles), vibrational wavenumbers, 1H and 13C NMR chemical shifts, UV-Vis. electronic transitions, the HOMO (highest occupied molecular orbital) and the LUMO (lowest unoccupied molecular orbital) analyses, NLO (non-linear optical properties) and the MEP (molecular electrostatic potential) surface have been computed by using the DFT/B3LYP quantum chemical method with 6-311++G(d,p) level of theory to compare with the experimental findings. Absorption bands of the molecule have computed around 300 and 360 nm, while observed at 244, 312 and 344 nm in the experimental UV-Vis. spectrum. Moreover, the mean polarizability value of the compound has been calculated 6.47 times greater than urea. The objective of the in silico investigation was to ascertain the biological effect profile of the title compound. The ADMETlab 2.0 web service has been employed to analyze the physicochemical, medicinal chemistry, metabolism, distribution, absorption, excretion and toxicity features of the compound. Its protein kinase CK2 inhibitory activity for the target macromolecule 5M4U has been investigated by means of a molecular docking study to investigate the anti-cancer activity of our flavonol derivative compound.