The novel compound N'-(2-phenylacetyl)picolinohydrazonamide (1) was readily synthesized via a metallic sodium-assisted reaction of 2-cyanopyridine with 2-phenylacetohydrazide in dry methanol. Characterization by FTIR and 1H NMR spectroscopy confirmed the structure. Single-crystal X-ray diffraction determined the crystal structure, and Hirshfeld surface analysis provided a detailed examination of the crystal packing. NMR studies indicated 1 adopts both E- and Z-isomeric forms in DMSO-d6. X-ray analysis revealed that molecules assemble into 1D supramolecular chains, stabilized mainly by N–H···O, N–H···N and C–H···O hydrogen bonds. Hirshfeld analysis quantified the intermolecular contacts, identifying H···X (X = H, C, N, O) and C···X (X = C, N) as predominant. The relative contributions of these interactions, particularly the dominance of hydrogen bonding in directing the crystal packing, were further quantified and compared using a set of theoretical calculations. Absorption, distribution, metabolism, excretion and toxicity (ADMET) properties and potential inhibitory activity against Human Aldose Reductase were computationally evaluation for 1, and compared to those of Epalrestat, which is a known Human Aldose Reductase inhibitor.
