In the present research work, a novel chalcone derivative (E)-3-(2-chlorophenyl)-1-(2-fluoro-4-methoxyphenyl)prop-2-en-1-one has been synthesized based on Claisen-Schmidt reaction by using aromatic aldehydes and aromatic ketones. A single crystal was obtained by recrystallization using cold ethanol and a gradual evaporation technique. It has been characterized by the single-crystal X-ray diffraction method. The synthesized crystal was found to be a monoclinic lattice with a P21/c space group. In Hirshfeld surface analysis dnorm shows that two red spots correspond to C-H-O contacts in hydrogen bonds and the 2D fingerprint highlighting the H...H interaction contributes 32.3% of the overall crystal packing. The optimized geometry of the title compound was obtained using B3LYP level of density functional theory calculation with a 631G(d,p) basis set. The title molecule docked to the active sites of the receptor 1KZN and the best binding confirmation was obtained.