Research Article: 2-Amino-N′-phenyl­benzohydrazide

Date Published: June 01, 2012

Publisher: International Union of Crystallography

Author(s): Víctor Kesternich, Paulo Gahona, Marcia Pérez-Fehrmann, Iván Brito, Matías López-Rodríguez.


In the title compound, C13H13N3O, the NNCO unit forms dihedral angles of 35.8 (1) and 84.0 (1)° with the benzene and phenyl rings, respectively. The dihedral angles between the aromatic rings is 61.2 (1)°. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, mol­ecules are linked by weak N—H⋯O hydrogen bonds into C(4) chains parallel to the c axis. Neighbouring chains are linked by weak N—H⋯N hydrogen bonds, forming R44(20) rings, and resulting in the formation of a two-dimensional network lying parallel to (010). The packing also features π–π stacking inter­actions between phenyl rings [centroid–centroid distance = 3.803 (2) Å].

Partial Text

For the pharmacological activity of quinazolinones, see: Kamal et al. (2010 ▶) and of benzotriazepinones, see: Filippakopoulos et al. (2012 ▶); Spencer et al. (2008 ▶). For the synthesis of the starting material 1H-benzo[d][1,3]oxazine-2,4-dione, see: Iwakura et al. (1976 ▶); Leiby & Heindel (1976 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).




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