Cyclohexanone 2-nitrophenylhydrazone

In the title Schiff base compound, C12H15N3O2, obtained from a condensation reaction of cyclohexanone and 2-nitrophenylhydrazine, the phenylhydrazone group is planar, the largest deviation from the mean plane being 0.0252 (12) Å, and the nitro fragment is twisted slightly with respect to the mean plane, making a dihedral angle of 6.96 (17)°. The cycloheaxanone ring displays a chair conformation. An intramolecular N—H⋯O hydrogen bond helps to stabilize the molecular structure.

In the title Schiff base compound, C 12 H 15 N 3 O 2 , obtained from a condensation reaction of cyclohexanone and 2-nitrophenylhydrazine, the phenylhydrazone group is planar, the largest deviation from the mean plane being 0.0252 (12) Å , and the nitro fragment is twisted slightly with respect to the mean plane, making a dihedral angle of 6.96 (17) . The cycloheaxanone ring displays a chair conformation. An intramolecular N-HÁ Á ÁO hydrogen bond helps to stabilize the molecular structure.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2561).
In the title compound, the phenylhydrazone group is planar with the largest deviation from the mean plane being 0.0252 (12)Å, the nitro fragment is sligthly twisted with respect to this mean plane making a dihedral angle of 6.96 (17)° (   Fig. 1). The cycloheaxanone displays a chair conformation as confirmed by the ring puckering parameters, θ= 5.6 (3)° and φ=195 (3)° (Cremer & Pople, 1975). The C-N and N-N distances within the hydrazone moity agree with related compound (Shan et al., 2003).
Intramolecular N-H···O hydrogen bond stabilizes the crystal structure.
Experimental 2-Nitrophenylhydrazine (1 mmol, 0.153 g) was dissolved in anhydrous ethanol (15 ml), The mixture was stirred for several minitutes at 351k, cyclohexanone (1 mmol, 0.098 g) in ethanol (8 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from methanol/dicholomethane(1:1), red single crystals of (I) was obtained after 3 d.

Refinement
All H atoms were positioned geometrically and treated as riding on their parent atoms with C-H=0.93Å (aromatic), 0.97Å(methylene) and N-H=0.86 Å, with U iso (H)=1.2U eq (C,N).

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 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.