Hydrazones exhibit a versatile chemistry and are of interest for their potential use as functional molecular systems capable of undergoing reversible changes of configuration, i.e. E/Z isomerization. The title compound, C12H12N4O, has an E configuration with respect to the hydrazone C=N bond. The crystal packing is formed by N-H...N and O-H...N hydrogen bonds that give a two-dimensional layer structure and C-H...C interactions associated with layer stacking to produce the three-dimensional supramolecular structure. These intermolecular interactions were analyzed and quantified by the Hirshfeld surface method and the two-dimensional supramolecular arrangement was topologically simplified as a hcb network.
Keywords: Hirshfeld surface; crystal structure; dynamic combinatorial chemistry; hcb network; hydrazinylidene; hydrogen bonding; methanol; reversible photo-induced E/Z isomerization; topology.