2-[4-(Azidomethyl)phenyl]benzonitrile

The title compound, C14H10N4, was obtained by a reaction of 4′-(bromomethyl)biphenyl-2-carbonitrile and sodium azide. The dihedral angle between the benzene rings is 46.41 (7)°. Weak intermolecular C—H⋯π interactions occur in the crystal.

Cg is the centroid of the C7-C12 benzene ring.

2-[4-(Azidomethyl)phenyl]benzonitrile Bo Peng Comment
At present, much attention in ferroelectric material field is focused on developing ferroelectric pure organic or inorganic compounds (Haertling et al. 1999;Homes et al. 2001). In order to find more dielectric ferroelectric materials, we investigate the physical properties of the title compound (Fig. 1). The dielectric constant of the title compound as a function of temperature indicates that the permittivity is basically temperature-independent (dielectric constant equaling to 3.5 to 4.8), suggesting that this compound should be not a real ferroelectrics or there may be no distinct phase transition occurred within the measured temperature range. Similarly, below the melting point (373 K) of the compound, the dielectric constant as a function of temperature also goes smoothly, and there is no dielectric anomaly observed (dielectric constant equaling to 3.5 to 4.8).Herein, we report the synthesis and crystal structure of the title compound,

2-[4-(azidomethyl)phenyl]benzonitrile.
Molecules of the title compound have normal geometric parameters. The bond lengths and angles are within their normal ranges. All benzene rings are planar and the azide group is linear.The dihedral angle between the benzene rings in the molecule is 46.41 (7). Dipole-dipole and van der Waals interactions are effective in the molecular packing.

Experimental
To a stirred solution of 4′-(bromomethyl)biphenyl-2-carbonitrile (5.42 g, 0.02 mol) in 30 mL of methanol, sodium azide (1.3 g, 0.02 mol) was added at the room temperature. The temperature was raised to 50°C in half an hour gradually and the mixture was stirred at this temperature for 12 h. The precipitate was filtered and washed with a small amount of water. The title compound was isolated using column chromatography (Petroleum ether: ethyl acetate-4:1). Single crystals suitable for X-ray diffraction analysis were obtained

Refinement
The H-atoms bonded to the C-atom were positioned geometrically and refined using a riding model, with C-H = 0.93 Å and U iso (H) = 1.2U eq (C).

Computing details
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure:  Perspective structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. 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.