4-(6-Quinolyloxymethyl)benzonitrile

The title compound, C17H12N2O, was synthesized by an ether synthesis from quinolin-6-ol and 4-(bromomethyl)benzonitrile. The phenyl ring of the benzonitrile group makes a dihedral angle of 47.52 (6)° with the plane of the quinoline fragment. The crystal structure is stabilized by intermolecular C—H⋯π interactions between a benzene H atom of the benzonitrile group and the benzene ring of the quinoline fragment. In addition, the crystal structure also exhibits a weak intermolecular C—H⋯N hydrogen bond.


Comment
The synthesis of new azoles has been a very active area of research and one important aspect has been the incorporation of functional units. Nitrile derivatives have found many industrial applications. For example, phthalonitriles have been used as starting materials for phthalocyanines (Jin et al., 1994), which are important components for dyes, pigments, gas sensors, optical limiters and liquid crystals, and which are also used in medicine, as singlet oxygen photosensitisers for photodynamic therapy (PDT; Brewis et al., 2003). Recently, we have reported a few benzonitrile compounds (Fu & Zhao, 2007;Zhao, 2008). As an extension of our work on the structural characterization, Here we present the synthesis and crystal structure of the title compound 4-[(quinolin-6-yloxy)methyl]benzonitrile (Fig. 1).
The phenyl ring (C11-C16) make a dihedral angle of 47.44 (1)° with the plane of the quinoline fragment. The molecular packing ( Fig. 2) is stabilized by intermolecular C-H···π interactions between the benzene H atom of benzonitrile group and the benzene ring of the quinoline fragment from an adjacent molecule, with a C12-H12···Cg i separation of 2.83 Å ( Fig. 2 and Table 1; Cg is the centroid of the C1-C4/C8/C9 benzene ring, symmetry code as in Fig. 2). Additionally, a weak intermolecular C-H···N hydrogen bond in the structure is observed ( Fig. 2 and Table 1).

Experimental
Quinolin-6-ol (1 g, 0.0069 mol) was added to a solution of sodium hydroxide (0.276 g, 0.0069 mol) in 15 ml of methanol and stirred for one hour. Then 4-(bromomethyl)benzonitrile (1.352 g, 0.0069 mol) was added to the above solution. The mixture was stirred at room temperature for 1 d. The title compound was isolated using column chromatography (petroleum ether:ethyl acetate = 2:1). Single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of ethyl acetate and tetrahydrofuran solution.

Refinement
All the C-H H atoms were calculated geometrically and with C-H distances ranging from 0.93 to 0.97 Å and were allowed to ride on the C and O atoms to which they are bonded. With which U iso (H) = 1.2Ueq(C). Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius. Fig. 2. The C-H···π and C-H···N interactions (dotted lines) in the title compound. Cg denotes the ring centroid. [Symmetry codes: (i) -x + 1/2, y + 1/2, -z + 1/2; (ii) x, y + 1, z; (iii) x, y -1, z; (iv) -x + 1/2, y -1/2, -z +

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 > 2sigma(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.