Structural, spectroscopic, computational, molecular docking and NLO analysis of a novel 1,3,4-oxadiazole

In this study, a new 1,3,4-oxadiazole derivative, N-benzyl-5-[2-(3-trifluoromethylphenyl) amino]phenyl-1,3,4-oxadiazol-2-amine, was synthesized and comprehensively characterized using experimental and theoretical methods. The compound was obtained in 79% yield, and its structure was investigated by FT-IR, ¹H NMR, ¹³C NMR, LC-MS, HSQC and single-crystal X-ray diffraction techniques. XRD analysis revealed that the molecule crystallizes in the monoclinic P2₁/c space group, and the structural parameters showed strong agreement with the DFT-optimized geometries (B3LYP/6-31G(d,p) and cc-pVDZ). Hirshfeld surface analysis indicated that H ⋯ H, C ⋯ H and H ⋯ F contacts dominate the crystal packing. Frontier molecular orbital (FMO) calculations demonstrated a HOMO-LUMO energy gap of approximately 4.1 eV, suggesting moderate chemical reactivity and stability. MEP, NCI-RDG, ELF and LOL analyses further clarified the electronic distribution and noncovalent interactions supporting structural stability. Nonlinear optical (NLO) calculations revealed that the compound possesses a first-order hyperpolarizability higher than urea and greater than KDP, indicating promising NLO potential. Molecular docking studies against human butyrylcholinesterase (PDB: 4BDS) showed a binding affinity of −7.8 kcal/mol with multiple stabilizing interactions, suggesting potential anti-Alzheimer's activity. Overall, the combined experimental and computational findings highlight the compound as a promising candidate for future optical and biological applications.