Abstract

In the title compound, C13H10BrN3O2·H2O, the conformation about the azomethine double bond is E. The mol-ecule exists in the amido form with a C=O bond length of 1.229 (2) Å. There is an intra-molecular O-H⋯N hydrogen bond forming an S(6) ring motif. The whole mol-ecule is almost planar, with an r.m.s. deviation of 0.021 Å for all non-H atoms, and the dihedral angle between the planes of the pyridine and benzene rings is 0.74 (12)°. In the crystal, the water mol-ecule of crystallization links the organic mol-ecules via Ow-H⋯O, Ow-H⋯N and N-H⋯Ow hydrogen bonds and short C-H⋯Ow contacts, forming sheets lying parallel to (100). Within the sheets there is a weak π-π inter-action involving the pyridine and benzene rings [centroid-to-centroid distance = 3.8473 (15) Å]. The sheets are linked via C-H⋯Br inter-actions, forming a three-dimensional network.

Highlights

  • In the title compound, C13H10BrN3O2H2O, the conformation about the azomethine double bond is E

  • Aroylhydrazones can coordinate to transition metals either in the amido form (Bessy Raj & Kurup, 2007) or in the iminolato form (Ghosh et al, 2005; Galić et al, 2011), leading to the formation of two types of complexes

  • Hydrazones derived from isonicotinoyl hydrazides are potential drugs for the treatment of the iron-overload associated diseases (Macková et al, 2012)

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Summary

Chemical context

Aroylhydrazones can coordinate to transition metals either in the amido form (Bessy Raj & Kurup, 2007) or in the iminolato form (Ghosh et al, 2005; Galić et al, 2011), leading to the formation of two types of complexes. Hydrazones derived from isonicotinoyl hydrazides are potential drugs for the treatment of the iron-overload associated diseases (Macková et al, 2012). Hydrazones have been used in chemical processes, in non-linear optics and as sensors as well as in catalytic processes (Hosseini-Monfared et al., 2013; Du & Hong, 2014). Their potential as analytical reagents (Galić et al, 2011) and their uses as molecular switches, metallo-assemblies and sensors have been reported

Structural commentary
Database survey
Supramolecular features
Synthesis and crystallization
Full Text
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