LAUSR

Abstract Hydrazone derivatives have drawn much attention because of their large pharmacological applications. In the present work, the compound (E)-2-((2,3-dimethylphenyl)amino)-N’-(furan-2-ylmethylene)benzohydrazide, noted C20H19N3O2 was synthesized, and its 3D structure was determined by X-ray crystallography. Structural characterization by X-ray crystallography was supported by Density Functional Theory (DFT) and Hartree Fock (HF) calculations. Intermolecular interactions in the crystal network were determined using Hirshfeld surface analyses. The optimized geometry, global reactivity descriptors, Natural Bond Orbital (NBO) analysis, and HOMO-LUMO of the molecule were computed using the DFT-B3LYP method and 6-311++G (d,p) basis set. The C20H19N3O2 has a monoclinic system and P21/c space group with parameters a = 13.8181 (10) A, b = 16.1969 (10) A, c = 8.1285 (7) A, β = 104.546 (6)° and Z = 4. It forms an S(6) ring motif with an intramolecular N—H⋯O hydrogen bond. Hirshfeld surface analysis and 2D fingerprint plots signify meaningful interactions in crystal packing [H⋯H (47.2%), C⋯H/H⋯C (29%), and O⋯H/H⋯O (13.3%) contacts]. Atomic charges were predicted using the Mulliken population and the NBO theory. The molecular electrostatic potential (MEP) picture was drawn using the same level of theory to visualize the chemical reactivity and charge distribution on the molecule. The local reactivity was examined by determining the Fukui functions and dual descriptor indices.