2-(2-Nitrophenyl)acetohydrazide

In the title compound, C8H9N3O3, the dihedral angle between the benzene ring and the acetohydrazide C—C(=O)—N—N plane [maximum deviation = 0.0471 (13) Å] is 87.62 (8)°. The nitro group is twisted by 19.3 (2)° with respect to the benzene ring. In the crystal, N—H⋯O hydrogen bonds link the molecules into a double-column structure along the b axis.

In the title compound, C 8 H 9 N 3 O 3 , the dihedral angle between the benzene ring and the acetohydrazide C-C( O)-N-N plane [maximum deviation = 0.0471 (13) Å ] is 87.62 (8) . The nitro group is twisted by 19.3 (2) with respect to the benzene ring. In the crystal, N-HÁ Á ÁO hydrogen bonds link the molecules into a double-column structure along the b axis.
ASP thanks UOM for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.
In the title compound, the dihedral angle between the benzene ring and acetohydrazide C2/C1/O1/N2/N1 plane is 87.62 (8)° (Fig. 1). The nitro group is twisted by 19.3 (2)° with the benzene ring. Bond lengths are in normal ranges (Allen et al., 1987). In the crystal, N-H···O hydrogen bonds (Table 1) link the molecules into a double-column structure along the b axis (Fig. 2).

Experimental
To a solution of methyl 2-(2-nitrophenyl)acetate (2 g, 10.14 mmol) in methanol (20 mL), hydrazine hydrate (2 mL) was added and the reaction mixture was stirred at room temperature for 8 hours (Fig. 3). After the completion of the reaction, methanol was removed under vacuum, water was added, precipitated solid was filtered and dried. The single crystal was grown from mixture methanol: water (2:1) by slow evaporation method and yield of the compound was 95%. (m.p.:

Refinement
Atoms H1A, H1B and H2 were refined with a bond-length restraint N-H = 0.86 (2) Å. All remaining H atoms were placed in their calculated positions and then refined using the riding model with C-H lengths of 0.93 Å (CH) and 0.97 Å (CH 2 ). Isotropic displacement parameters were set to 1.2 times U eq of the parent atom. The Flack parameter 0.3 (3) and the Hooft y parameter of 0.45 (18) imply that the crystal used was an inversion twin.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.