2-{4-[(Quinolin-8-yloxy)methyl]phenyl}benzonitrile

In the title compound, C23H16N2O, the bond angle at the O atom that connects the benzene ring and the quinoline ring system is 116.0 (2)°. The quinoline ring system make a dihedral angle of 16.5 (2)° with the adjacent benzene ring. The dihedral angle between the biphenyl benzene rings is 70.8 (2)°.

In the title compound, C 23 H 16 N 2 O, the bond angle at the O atom that connects the benzene ring and the quinoline ring system is 116.0 (2) . The quinoline ring system make a dihedral angle of 16.5 (2) with the adjacent benzene ring. The dihedral angle between the biphenyl benzene rings is 70.8 (2) .

Comment
Tetrazole compounds have been studied for more than one hundred years and applied in various areas (Hang et al., 2009).
As a part of systematic investigation of new tetrazole compounds and discovery of new coordination mode (Xiong et al., 2002), we get the synthesis of the title compound C22 H16 N2 O,and preparation of tetrazoles in situ synthesis of tetrazole through cycloaddition between organotin azide and organic cyano group (Ye et al., 2006;Chen et al., 2010).
In the asymmetric unit of the title compound, the planes angle between the two benzene rings is 70.8°. O1 connect quinoline ring and sartan ring with a 115.9 bond-angle and the bond length O1-C10 is 1.4261 (35) Å, O1-C9 is 1.3691 (33) Å). The quinoline ring make a small dihedral angle of 16.5° with adjacent benzene ring (Fig 1). Fig 2 shows that the molecules assemble as straight chain in the crystal structure along the a axis.
Experimental 8-hydroxyquinoline(1.45 g,10 mmol) was added in a solution of 4'-Bromoethyl-2-cyanobiphenyl(2.71 g,10 mmol) in methanol(20 ml).After the mixture was stirred for 10 h at 355 K,the precipitate was filtered off and the solution was evaporated in vacuum. The crude product was then crystallized form ethanol to yield colourless prisms of the title compound.

Refinement
H atoms were positioned geometrically, with C-H = 0.93 and 0.97 Å for aromatic and methylene H respectively, and constrained to ride on their parent atoms with Uĩso~(H) = xU~eq~(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms. Fig. 1. Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 30% probability level.

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 supplementary materials sup-3 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.