The current research work is about the synthesis of functionalized crystalline anilide, i.e., (Z)-4-((2-nitrophenyl)amino)-4-oxobut-2-enoic acid (NAOB) and its experimental and theoretical investigation. The single-crystal X-rays diffraction technique is employed for the crystal structure determination. The crystal structure of NAOB is compared with two closely related crystal structures of the literature that contain nitro group at the para position of the phenyl ring. The supramolecular assembly was thoroughly explored by Hirshfeld surface analysis. The most probable contact for the crystal packing interactions was determined by enrichment ratio analysis. The crystal packing environment was explored by the interaction energy between the molecular pairs. Energy frameworks were computed to understand the topology of the single crystal of the compound NAOB. Void analysis was performed to check the strength of the crystal packing. In order to visualize the relative polarity and active sites of crystal structure, molecular electrostatic potential (MEP) study was performed. The DFT-based calculated results were found in agreement with the experimental results.Graphical abstract: