N′-[(E)-(3-Fluoropyridin-2-yl)methylidene]pyridine-3-carbohydrazide dihydrate

Abstract

The organic molecule in the title dihydrate, C12H9FN4O·2H2O, exists in the E conformation with respect to the azomethane C=N double bond. The molecule is approximately planar, with a maximum deviation of 0.117 (1) Å for the carbonyl O atom from the mean plane of the molecule. Both pyridine rings are essentially coplanar with the central C(=O)N2C unit [dihedral angles = 1.99 (7) and 5.71 (8)°], exhibiting a significant difference in dihedral angles from its benzohydrazide analogue. The crystal packing features N—H...O, O—H...N and O—H...O hydrogen-bond interactions, which lead to the formation of a chain along the c-axis direction through one of the water molecules present, and these chains are stacked one over the other by means of π–π interactions [with centroid–centroid distances of 3.7099 (10) and 3.6322 (10) Å] between the aromatic rings in neighbouring antiparallel molecules, building a three-dimensional supramolecular network.