2-(4-Methylphenoxy)acetohydrazide

In the title compound, C9H12N2O2, the acetohydrazide group is approximately planar [maximum deviation = 0.034 (2) Å]. In the crystal, molecules are linked via intermolecular N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds into infinite two-dimensional networks parallel to (001).

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009). HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for the award of a USM fellowship. AMI is thankful to the Director of the National Institute of Technology for providing research facilities and also thanks the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for a Young Scientist Award.

Comment
The full therapeutic possibilities of hydrazides were realized after the discovery of isonicotinic acid hydrazide (INH). Hydrazides and their derivatives have been described as useful synthons of various heterocyclic rings (Isloor et al., 2009;Holla & Udupa, 1992). A large number of hydrazides and their derivatives are reported to possess a broad spectrum of biological activities (Ozdemir et al., 2009;Khattab, 2005). The most widely used method to prepare hydrazides is hydrazinolysis of the corresponding esters with hydrazine hydrate (Yale et al., 1953). Prompted by the diverse activities of hydrazides and its derivatives, we have synthesized the title compound to study its crystal structure.

Refinement
H1N1, H1N2 and H2N2 were located in a difference Fourier map and allowed to refined freely. The remaining H atoms were positioned geometrically and refined using a riding model with C-H = 0.93 -0.97 Å and U iso (H) = 1.2 or 1.5 U eq (C).
The highest residual electron density peak is located at 0.94 Å from H9C and the deepest hole is located at 0.94 Å from C8. Fig. 1

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 > 2sigma(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.