TY - JOUR

T1 - N′-[1-(5-Bromo-2-hydroxyphenyl)ethylidene]isonicotinohydrazide monohydrate

T2 - crystal structure and Hirshfeld surface analysis

AU - Lee, See Mun

AU - Halcovitch, Nathan R.

AU - Jotani, Mukesh M.

AU - Tiekink, Edward R. T.

PY - 2017/4/1

Y1 - 2017/4/1

N2 - 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.

AB - 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.

KW - carbohydrazide

KW - crystal structure

KW - halogen bonding

KW - Hirshfeld surface analysis

KW - hydrogen bonding

U2 - 10.1107/S2056989017004790

DO - 10.1107/S2056989017004790

M3 - Journal article

AN - SCOPUS:85017324419

VL - 73

SP - 630

EP - 636

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

ER -