In this research, we have compared theoretical and experimental results such as the molecular structure, vibration frequencies, UV-Vis, chemical shift values of H-1 and C-13 NMR of (E)-N-(4-nitrobenzylidene)-3-chlorobenzenamine (NBCA). The experimental data have been collected from a high-resolution X-ray diffraction pattern and the theoretical analyses have been carried out using the density functional theory (DFT) based on B3LYP level at 6-31++G (d, p) by Gaussian program, knowing that every single vibration frequency is awarded on the potential energy distribution (PED) base and electronic transitions are computed according to the time-dependent density functional theory (TD-DFT). The non-linear optical parameters (NLO) have similarly been investigated at the same level theory. The energies of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) and the global chemical reactivity descriptors (GCRD) of the title molecule were investigated by using DFT/B3LYP/6-311++G (d, p) method. Molecular electrostatic potential (MEP) is simulated to look for better reactive sites for electrophilic and nucleophilic attacks. To ascertain the contribution of intermolecular interactions, Hirshfeld surface analysis and fingerprint plots were carried out. To determine the biological activity of NBCA molecule, the basic prediction of substance activity spectra (PASS) and molecular docking are studied. (C) 2021 Elsevier B.V. All rights reserved.