2-[4-(Azido­meth­yl)phen­yl]benzonitrile

Bo Peng

doi:10.1107/S1600536812029261

. 2012 Jun 30;68(Pt 7):o2297. doi: 10.1107/S1600536812029261

2-[4-(Azidomethyl)phenyl]benzonitrile

Bo Peng ^a,^*

PMCID: PMC3394073 PMID: 22798938

Abstract

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.

Related literature

For background literature, see: Haertling (1999 ▶); Homes et al. (2001 ▶).

Experimental

Crystal data

C₁₄H₁₀N₄
M _r = 234.26
Triclinic,
a = 8.0763 (16) Å
b = 8.2183 (16) Å
c = 10.116 (2) Å
α = 76.22 (3)°
β = 69.36 (3)°
γ = 85.94 (3)°
V = 610.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
6204 measured reflections
2748 independent reflections
1559 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.146
S = 1.02
2748 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029261/xu5575sup1.cif

e-68-o2297-sup1.cif^{(14.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029261/xu5575Isup2.hkl

e-68-o2297-Isup2.hkl^{(134.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812029261/xu5575Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯Cg ⁱ	0.97	2.75	3.642 (3)	154

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

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