A new Schiff-base (Z)-4-bromo-2-(((2,4-dimethoxyphenyl)imino)methyl)-5-fluorophenol (BDMF) was synthesized and characterized by single-crystal X-ray diffraction, spectroscopic (UV, FT-IR, and NMR), and DFT techniques.Based on DFT computational anal., Mol. Electrostatic Potential (MESP) 3D plots were used to identify the electrophilic and nucleophilic sites.Based on HOMO-LUMO energies, charge transfer takes place within the mol., and quantum chem. characteristics were precisely assessed.Addnl., DFT was used to examine charges, MO contributions, natural bond orbital (NBO), frontier MO (FMO), nonlinear optic (NLO) anal., and thermodn. parameters including enthalpy, entropy, and heat capacity at different temperaturesValues for polarizability, elec. dipole moment, and first static hyperpolarizability have been computed.The title compound exhibits nonlinear optical properties, according to the results.In addition, Hirshfeld surface anal. was used to predict mol. interactions.Finally, mol. docking anal. of the title compound was performed.