Structural, Spectroscopic, and DFT Studies of N'-(2,4-difluorobenzylidene)-2-furoic Hydrazide for Electronic and Therapeutic Applications.

Abstract

A single crystal of N'-(2,4-difluorobenzylidene)-2-furoic hydrazide (DFBFH) was grown using the slow evaporation method with ethanol as the solvent. Single crystal X-ray diffraction (XRD) analysis revealed that DFBFH crystallizes in the monoclinic system, space group P2₁/c, with unit cell parameters: a = 13.0872(12) Å, b = 7.7520(8) Å, c = 11.9055(11) Å, α = γ = 90˚, β = 110.301(4)˚, V = 1132.81(19) ų, Z = 4, and a density of 1.467 Mg/m³. The crystal structure is stabilized by intermolecular hydrogen bonding, forming one-dimensional chains along the [001] direction through C2-H2···O2 and C6-H6···F1 interactions. Hirshfeld surface analysis was conducted to examine the voids, energy framework, and intermolecular interaction energies. The electron density distribution and nonlinear optical (NLO) properties were evaluated using density functional theory (DFT) at the B3LYP/6-311 + + G(d, p) level. Theoretical results indicate that DFBFH exhibits significantly higher hyperpolarizability than urea, suggesting promising NLO behaviour. DFBFH also shows strong fluorescence at 568 nm due to π-π* transitions enhanced by n-π* excitation. Molecular docking studies with breast cancer-related proteins (PDB IDs: 4XEO, 3O96, 5KCV, and 2YJA) yielded binding energies of - 8.2, - 8.0, - 7.9, and - 7.8 kcal/mol, respectively, indicating that DFBFH may possess notable anti-breast cancer potential.