The structural, spectral, electronic, thermodynamic and nonlinear optical features of 4-[(1,3-dioxoisoindolin-2-yl)methyl]benzenesulfonamide were investigated using experimental and theoretical methods. Experimental characterization was carried out via FT-IR, Raman, carbon-13 and proton NMR chemical shifts and UV-Vis. spectroscopic techniques. The molecular electronic structure computations were done with DFT/B3LYP method using the 6-311++G(2d,2p) basis set. VEDA4 software was used to analyze in PED (potential energy distribution) to vibrational profile of computed harmonic frequencies. Hirshfeld surface analysis was performed to determine interactions in crystal packing of the compound. Additionally, the highest occupied molecular orbitals (HOMOs), lowest unoccupied molecular orbitals (LUMOs), nonlinear optical (NLO) analysis, molecular electrostatic potential (MEP and ESP) surfaces and thermochemical properties were studied with theoretical computational method. The localization contributions on the defined molecular groups of molecular orbitals in the electronic transitions were investigated. Enzyme-ligand interactions of 4-[(1,3-dioxoisoindolin-2-yl)methyl]benzenesulfonamide with carbonic anhydrase II were investigated by molecular docking analysis. The experimental and calculated structural and spectroscopic data were compared with each other. The correlation between computed results and experimental records is in a good harmony.