2-(2,3-Dimethylanilino)benzohydrazide

In the title compound, C15H17N3O, the dihedral angle between the benzene rings is 58.05 (9)°. The non-H atoms of the hydrazide group lie in a common plane (r.m.s. deviation = 0.0006 Å) and are close to coplanar with their attached benzene ring [dihedral angle = 8.02 (9)°]. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif in the molecule, and a short intramolecular contact (H⋯H = 1.88 Å) is also observed. In the crystal, molecules are linked by pairs of N—H⋯N hydrogen bonds into inversion dimers. The crystal packing also features C—H⋯π interactions.

The molecular structure of the title compound is shown in Fig. 1. The C1-C6 benzene ring makes a dihedral angle of 58.05 (9)° with the C7-C12 benzene ring. The non-H atoms of hydrazide group (O1/N2/N3/C13) lie nearly on a plane [r.m.s. deviation = 0.0006 Å] and are nearly coplanar with the attached C7-C12 benzene ring as indicated by the dihedral angle of 8.02 (9)°. An intramolecular N1-H1N1···O1 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995) in the molecule. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those in a related structure (Bhat et al., 2012).

Experimental
The title compound was prepared by the reaction of the methyl ester of fenamic acid with hydrazine hydrate or with the direct reaction of fenamic acid with hydrazine hydrate under microwave irritation (Reddy et al., 2010;Aboul-Fadl et al., 2011). Brown blocks were grown from the slow evaporation of a methanol solution.

Refinement
The N-bound H atoms were located in a difference Fourier map and refined freely [N-H = 0.89 (2)

Figure 2
The crystal packing of the title compound viewed along the a axis. The dashed lines represent the hydrogen bonds. For clarity sake, hydrogen atoms not involved in hydrogen bonding have been omitted.

sup-3
Acta Cryst. (2012). E68, o2527-o2528  (Cosier & Glazer, 1986) operating at 100.0 (1) K. Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.