Date Published: May 01, 2009
Publisher: International Union of Crystallography
Author(s): Yousef M. Hijji, Oyebola Oladeinde, Ray J. Butcher, Jerry P. Jasinski.
In the title molecule, C12H11N3O2, the dihedral angle between the mean planes of the naphthalene and carboxamide groups is 28.9 (8)°. The hydrazine N atoms are twisted slightly out of the plane of the carboxamide group [C—C—N—N torsion angle = −175.06 (13)°]. The crystal packing is influenced by N—H⋯O hydrogen bonding which includes a bifurcated hydrogen bond between the amide N atom and nearby carboxyl and hydroxyl O atoms. A second bifurcated hydrogen bond occurs between the hydroxyl O atom and nearby amide (intermolecular) and hydrazine (intramolecular) N atoms. As a result, molecules are linked into a co-operative hydrogen-bonded network of infinite one-dimensional O—H⋯O—H⋯O—H chains along the (101) plane of the unit cell in a zigzag pattern, the dihedral angle between the mean planes of the naphthalene groups of adjacent molecules in the chain being 86.9 (2)°. A MOPAC PM3 calculation provides support to these observations.
For related semicarbazones, see: Noblia et al. (2005 ▶). For the bioactivity of semicarbazones, see: Beraldo & Gambino (2004 ▶). For their applications in polymers, see: Khuhawar et al. (2004 ▶) and in sensors, see: Oter et al. (2007 ▶).