3-[2-(4,4-Dimethyl-2,6-dioxocyclo­hexyl­idene)hydrazin­yl]benzonitrile

The title compound, C15H15N3O2, contains benzonitrile and 4,4-dimethyl-2,6-dioxocyclo­hexyl­idene groups connected via a hydrazinyl group. The structure is in the hydrazone tautomeric form in the solid state. The benzonitrile and hydrazinyl groups (3-hydrazinylbenzonitrile) are essentially coplanar with an r.m.s. deviation of 0.016 Å. Intra­molecular N—H⋯O hydrogen bonding helps to stabilize the mol­ecular structure, and weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure

4-[2-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-yl­idene)hydrazin-1-yl]benzo­nitrile

In the title compound, C13H11N3O4, the dioxane ring adopts an envelope conformation with the C atom bonded to the dimethyl group in the flap position [deviation = 0.613 (1) Å]. The nitrile group and the attached benzene ring are roughly coplanar [maximum deviation = 0.087 (1) Å]. An intra­molecular N—H⋯O hydrogen bond involving the hydrazinyl group generates an S(6) ring. The N—N and C—N bond lengths indicate that the compound may be a mixture of the azo and hydrazone tautomeric forms but the presence of the N-bound H atom supports the hydrazone form. The crystal structure is stabilized by weak inter­molecular C—H⋯O, C—H⋯N and C—H⋯π inter­actions

Modern Trends of Organic Chemistry in Russian Universities

© 2018, Pleiades Publishing, Ltd. This review is devoted to the scientific achievements of the departments of organic chemistry in higher schools of Russia within the past decade