Nicotinohydrazide

The title mol­ecule (alternative name: pyridine-3-carbohydrazide; C(6)H(7)N(3)O) was obtained from the reaction of ethyl nicotinate with hydrazine hydrate in methanol. In the amide group, the C—N bond is relatively short, suggesting some degree of electronic delocalization in the mol­ecule. The stabilized conformation may be compared with those of isomeric compounds picolinohydrazide (pyridine-2-carbohydrazide) and isonicotinohydrazide (pyridine-4-carbohydrazide). In the title isomer, the pyridine ring forms an angle of 33.79 (9)° with the plane of the non-H atoms of the hydrazide group. This lack of coplanarity between the hydrazide functionality and the pyridine ring is considerably greater than that observed in isonicotinohydrazide (dihedral angle = 17.14°), while picolinohydrazide is almost fully planar. The title isomer forms inter­molecular N—H⋯O and N—H⋯N hydrogen bonds, which stabilize the crystal structure.