2-[(Anilino)(2-nitrophenyl)methyl]cyclohexanone

In the title compound, C19H20N2O3, the cyclohexanone ring adopts a chair conformation with the aminomethyl group is positioned equatorially. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, molecules are linked by N—H⋯O hydrogen bonds.


Experimental
The title compound was obtained by adding of 0.04 g of Laponite-HMPC nano composite (Eftekhari-Sis et al., 2012a,b) to a mixture of 0.5 mmol of 2-nitrobenzaldehyde, 0.5 mmol of aniline and 3 equiv. of cyclohexanone and stirring at room temperature for 24 h. After completion of the reaction, 5 ml EtOH was added and catalyst was removed by filtration, and filtrate was concentrated under reduced pressure. The obtained crud product was recrystallized from EtOH to afford title compound in 62% yield. Colorless crystals suitable for crystal structure determination were grown from EtOH.

Refinement
Carbon bound H atoms were positioned geometrically, with C-H=0.93, 0.97, and 0.98 Å for aromatic, methylene and methine H, and constrained to ride on their parent atoms, with U iso (H) = 1.2Ueq(C). The nitrogen H atoms were located from the difference Fourier map allowed to refine freely.  The structure of title compound, showing 35% probability displacement ellipsoids and the atom numbering scheme.

Computing details
Intramolecular hydrogen bond are shown as dashed lines.

Figure 2
The stabilization of molecules in the crystal by inter-and intramolecular N-H···O hydrogen bonds and C-H···O interactions.

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 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.