Abstract
The asymmetric unit of the title aroyl hydrazone Schiff base salt, C13H12N3O2+·N O3-, consists of one mol-ecular 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⋯O hydrogen bond. The mol-ecule overall is non-planar, with the pyridinium and benzene rings being inclined to each other by 4.21 (4)°. In the crystal, cations and anions are linked via inter-molecular O-H⋯O and bifurcated N-H⋯O hydrogen bonds, forming a two-dimensional network parallel to (101). These networks are further linked by C-H⋯O hydrogen bonds, forming slabs parallel to (101). The slabs are linked by offset π-π inter-actions, involving the benzene and pyridinium rings of adjacent slabs [inter-centroid distance = 3.610 (2) Å], 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⋯O/O⋯H (45.1%), H⋯H (19.3%), H⋯C/C⋯H (14.5%), H⋯N/N⋯H (7.9%) and C⋯C (6.0%) inter-actions.
Highlights
Hydrazone Schiff bases and their coordination compounds have gained importance recently because of their application as models in biological, analytical and antimicrobial systems, and due to their anticancer, antibacterial as well as antifungal activities (Ruben et al, 2003)
The structure determination of the title aroyl hydrazone Schiff base salt was undertaken in order to compare the results obtained with those reported previously
The asymmetric unit of the title aroyl hydrazone Schiff base salt contains one molecular cation and one nitrate anion, which are linked via an N+—HÁÁÁO hydrogen bond (Fig. 1, Table 1)
Summary
Hydrazone Schiff bases and their coordination compounds have gained importance recently because of their application as models in biological, analytical and antimicrobial systems, and due to their anticancer, antibacterial as well as antifungal activities (Ruben et al, 2003). Aroyl hydrazones are a class of versatile ligands, capable of generating various molecular architectures and coordination polyhedra (Ruben et al, 2003; Uppadine Gisselbrecht & Lehn, 2004; Uppadine & Lehn, 2004; Wood et al, 2004). Aroyl hydrazones are obtainable through hydrazide-ketone/aldehyde condensation, and they exhibit flexible metal-chelating capabilities through their keto–enol tautomerism and possible reversible deprotonation. The structure determination of the title aroyl hydrazone Schiff base salt was undertaken in order to compare the results obtained with those reported previously. In this context, we synthesized the title compound, (E)-4-{[2(4-hydroxybenzoyl)hydrazin-1-ylidene]methyl}pyridin-1-ium nitrate, and report on its crystal and molecular structures along with the Hirshfeld surface analysis
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