2-(4-Methylphenyl)benzonitrile

In the title compound, C14H11N, the dihedral angle between the mean planes of the two benzene rings is 44.6 (7)°. The crystal packing is stabilized by weak intermolecular π–π stacking interactions, the centroid–centroid distances being 3.8172 (12) and 3.9349 (12) Å.

In the title compound, C 14 H 11 N, the dihedral angle between the mean planes of the two benzene rings is 44.6 (7) . The crystal packing is stabilized by weak intermolecularstacking interactions, the centroid-centroid distances being 3.8172 (12) and 3.9349 (12) Å .
MSS thanks the University of Mysore for the research facilities and R. L. Fine Chem, Bangalore, India, for the gift of the sample. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.
In the title compound, C 14 H 11 N,, the dihedral angle between the mean planes of the two benzene rings is 44.6 (7)° ( Fig.   1). Bond lengths and angles are in normal positions (Allen et al., 1987). Crystal packing is stabilized by weak π-π stacking interactions ( Fig. 2, Table 1).

Experimental
The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore. X-ray quality crystals were obtained by slow evaporation of methanol solution (m.p.: 323-325 K).

Refinement
All of the H atoms were placed in their calculated positions and then refined using the riding model with C-H = 0.95 Å (aromatic) or 0.98 Å (CH 3 ). Isotropic displacement parameters for these atoms were set to 1.19-1.21 (aromatic) or 1.50 (CH 3 ) times U eq of the parent atom.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq   (8)