Crystal structure and Hirshfeld surface analysis of (E)-4-{[2-(4-hydroxybenzoyl)hydrazin-1-yl-idene]methyl}pyridin-1-ium nitrate

The asymmetric unit of the title aroyl hydrazone Schiff base salt, C13H12N3O2+center dot N O-3(-), consists of one molecular cation in the keto tautomeric form, adopting an E configuration with respect to the azomethine bond, and one nitrate anion. The two units are linked via an N-H center dot center dot center dot O hydrogen bond. The molecule overall is non-planar, with the pyridinium and benzene rings being inclined to each other by 4.21 (4)degrees. In the crystal, cations and anions are linked via intermolecular O-H center dot center dot center dot O and bifurcated N-H center dot center dot center dot O hydrogen bonds, forming a two-dimensional network parallel to (101). These networks are further linked by C-H center dot center dot center dot O hydrogen bonds, forming slabs parallel to (101). The slabs are linked by offset pi-pi interactions, involving the benzene and pyridinium rings of adjacent slabs [intercentroid distance = 3.610 (2) angstrom], forming a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H center dot center dot center dot O/O center dot center dot center dot H (45.1%), H center dot center dot center dot H (19.3%), H center dot center dot center dot C/C center dot center dot center dot H (14.5%), H center dot center dot center dot N/N center dot center dot center dot H (7.9%) and C center dot center dot center dot C (6.0%) interactions.