N′-[1-(5-Bromo-2-hydroxyphenyl)ethylidene]isonicotinohydrazide monohydrate:crystal structure and Hirshfeld surface analysis

Lee, See Mun and Halcovitch, Nathan R. and Jotani, Mukesh M. and Tiekink, Edward R. T. (2017) N′-[1-(5-Bromo-2-hydroxyphenyl)ethylidene]isonicotinohydrazide monohydrate:crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E: Crystallographic Communications, 73. pp. 630-636.

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Abstract

In the title isonicotinohydrazide hydrate, C14H12BrN3O2·H2O {systematic name: N′-[(1E)-1-(5-bromo-2-hydroxyphenyl)ethylidene]pyridine-4-carbohydrazide monohydrate}, the central CN2O region of the organic molecule is planar and the conformation about the imine-C=N bond is E. While an intramolecular hydroxy-O-H⋯N(imine) hydrogen bond is evident, the dihedral angle between the central residue and the benzene rings is 48.99(9)°. Overall, the molecule is twisted, as seen in the dihedral angle of 71.79(6)° between the outer rings. In the crystal, hydrogen-bonding interactions, i.e. hydrazide-N-H⋯O(water), water-O-H⋯O(carbonyl) and water-O-H⋯N(pyridyl), lead to supramolecular ribbons along the a-axis direction. Connections between these, leading to a three-dimensional architecture, are mediated by Br⋯Br halogen bonding [3.5366(3)Å], pyridyl-C-H⋯O(carbonyl) as well as weak π-π interactions [inter-centroid separation between benzene rings = 3.9315(12)Å]. The Hirshfeld surface analysis reveals the importance of hydrogen atoms in the supramolecular connectivity as well as the influence of the Br⋯Br halogen bonding.

Item Type:
Journal Article
Journal or Publication Title:
Acta Crystallographica Section E: Crystallographic Communications
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/3100/3104
Subjects:
ID Code:
85944
Deposited By:
Deposited On:
20 Apr 2017 09:06
Refereed?:
Yes
Published?:
Published
Last Modified:
16 Nov 2020 07:22