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

Acta Crystallographica Section E: Crystallographic Communications

Nathan R. Halcovitch¹  Mukesh M. Jotani²  See Mun Lee³  Edward R. T. Tiekink³ 

[1] Department of Chemistry, Lancaster University, Lancaster LA1 4YB, United Kingdom;Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India;Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia;

关键词: crystal structure;    carbohydrazide;    hydrogen bonding;    halogen bonding;    Hirshfeld surface analysis;   

DOI  :  10.1107/S2056989017004790

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown