(E)-N′-(3,4-Dimethoxybenzylidene)nicotinohydrazide monohydrate

Abstract

In the title hydrated compound, C15H15N3O3·H2O, the nicotinohydrazide mol­ecule adopts a trans conformation with respect to the C=N double bond. The dihedral angle between the benzene and pyridine rings is 5.10 (14)°. In the crystal, the solvent water mol­ecule acts as an acceptor, forming an N—H⋯O hydrogen bond supported by two C—H⋯O contacts. It also acts as a donor, forming bifurcated O—H⋯(O,O) and O—H⋯N hydrogen bonds that combine with the former contacts to form zigzag chains of mol­ecules along the c-axis direction. An additional O—H⋯O donor contact completes a set of six hydrogen bonds to and from the water mol­ecule and connects it to a third nicotinohydrazide mol­ecule. This latter contact combines with weaker C—H⋯O hydrogen bonds supported by a C—H⋯π contact to stack mol­ecules along b in a three-dimensional network.

Crystal structure, Hirshfeld surface analysis and HOMO–LUMO analysis of (E)-N′-(3-hydroxy-4-methoxybenzylidene)nicotinohydrazide monohydrate

“…A search of the Cambridge Structural Database (Version 5.40, update November 2018; Groom et al, 2016) for uncoordinated N 0 -(benzylidene)nicotinohydrazide derivatives O-substituted at the 3,4 positions of the benzene ring yielded three hits, namely N 0 -(1,3-benzodioxol-5-ylmethylene)nicotinohydrazide monohydrate (refcode BUDNIY; Bao et al, 2009), N 0 -(3,4dimethoxybenzylidene)nicotinohydrazide monohydrate (XODZOH; Novina et al, 2014) and the isomer N 0 -(4-hydroxy-3-methoxybenzylidene)nicotinohydrazide monohydrate (SEZREV; Shi et al, 2007). The conformation of the last molecule differs from the title compound mainly in the relative orientation of the pyridine ring with respect to the carbonyl group, as indicated by the value of 158.03 (15) for the O1-C6-C1-C2 torsion angle in the title compound and of 10.2 (3) for the corresponding angle in SEZREV.…”

Crystal structure of (E)-3-{[2-(2,4-dichlorobenzylidene)hydrazin-1-yl]carbonyl}pyridinium chloride trihydrate

“…For the biological activity of hydrazones, see: Kaplancikli et al (2012); Babahan et al (2013). For related structures, see: Novina et al (2013Novina et al ( , 2014 H atoms treated by a mixture of independent and constrained refinement Á max = 0.28 e Å À3 Á min = À0.37 e Å À3 Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) x þ 1; y; z; (ii) Àx þ 2; Ày þ 1; Àz þ 1; (iii) Àx þ 1; Ày þ 1; Àz; (iv) Àx þ 1; Ày þ 1; Àz þ 1;…”

“…Moreover, the hydrazone group plays an important role of the antimicrobial and possesses interesting antibacterial, antifungal and anti-tubercular activities (Babahan et al, 2013). As part of our studies on hydrazone derivatives (Novina et al, 2013;2014), we report herein the crystal structure of the title compound.…”

Crystal structure of 3-({[(thiophen-2-yl)methylidene]hydrazinyl}carbonyl)pyridinium chloride dihydrate

“…For structures of related hydrazone derivatives, see: Cheng et al (2008); Jing et al (2007); Novina et al (2013Novina et al ( , 2014. For the biological activity of hydrazones, see: Babahan et al (2013); Kaplancikli et al (2012).…”