Methyl N′-[(E)-1-phenylethylidene]hydrazinecarboxylate

The molecule of the title compound, C10H12N2O2, adopts a trans configuration with respect to the C=N bond. The dihedral angle between the phenyl ring and the hydrazine carboxylic acid mean plane is 25.23 (9)°. In the crystal structure, molecules are linked into chains by N—H⋯O hydrogen bonds and C—H⋯π interactions.

The molecule of the title compound, C 10 H 12 N 2 O 2 , adopts a trans configuration with respect to the C N bond. The dihedral angle between the phenyl ring and the hydrazine carboxylic acid mean plane is 25.23 (9) . In the crystal structure, molecules are linked into chains by N-HÁ Á ÁO hydrogen bonds and C-HÁ Á Á interactions.

Related literature
For a related structure and background, see: Cheng (2008 Table 1 Hydrogen-bond geometry (Å , ).

Comment
As part of our ongoing studies of benzaldehydehydrazone derivatives (Cheng, 2008), we now report the synthesis and structure of the title compound, (I).
In the crystal structure, N-H···O hydrogen bonds and C-H···π interactions (Table 1)  Experimental Acetophenone (1.2 g, 0.01 mol) and methyl hydrazinecarboxylate (0.9 g, 0.01 mol) were dissolved in stirred methanol (20 ml) and left for 2 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 90% yield. Colourless blocks of (I) were obtained by slow evaporation of a ethanol solution at room temperature (m.p. 450-452 K).

Refinement
Anomalous dispersion was negligible and Friedel pairs were merged before refinement. The H atoms attached to C7 and N2 were located in a difference map and their positions and U iso values were freely refined. The other H atoms were geometrically placed (C-H = 0.95-0.98Å) and refined as riding with U iso (H) = 1.2-1.5U eq (C). Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids for the non-hydrogen atoms.

Special details
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 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.