N′-(2-Methoxybenzylidene)-2-nitrobenzohydrazide

The title compound, C15H13N3O4, was synthesized by the reaction of equimolar quantities of 2-methoxybenzaldehyde and 2-nitrobenzohydrazide in methanol. The dihedral angle between the two substituted benzene rings is 68.3 (2)°. In the crystal structure, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur.

The title compound, C 15 H 13 N 3 O 4 , was synthesized by the reaction of equimolar quantities of 2-methoxybenzaldehyde and 2-nitrobenzohydrazide in methanol. The dihedral angle between the two substituted benzene rings is 68.3 (2) . In the crystal structure, inversion dimers linked by pairs of N-HÁ Á ÁO hydrogen bonds occur.

Comment
Hydrazone compounds have received considerable attention due to their pharmacological properties (Beraldo & Gambino, 2004). In the last few years, the crystal structures and properties of a series of hydrazone compounds have been reported (Galić et al., 2001;Richardson & Bernhardt, 1999;Ali et al., 2004). As a continuation of work on these compounds, we report here the structure of the title compound, (I) Fig. 1.

Experimental
The title compound was synthesized by the reaction of equimolar quantities (1.0 mmol each) of 2-methoxybenzaldehyde and 2-nitrobenzohydrazide in methanol (100 ml) for 3 h at room temperature. The solution was kept in air for a few days, forming colorless block-like crystals of the compound.

Refinement
The N-bound H atom was located in a difference Fourier map and was refined with an N-H distance restraint of 0.90 (1) Å.
C-bound H atoms were placed in calculated positions (C-H = 0.93-0.96 Å) and refined using a riding model with U iso (H) = 1.2U eq (C) and 1.5U eq (C15). Crystals were small and weakly diffracting which explains the relatively low data fraction. Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Figures
supplementary materials sup-2   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 Rfactors(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.