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

Bin Wei

doi:10.1107/S1600536811012724

. 2011 Apr 29;67(Pt 5):o1209. doi: 10.1107/S1600536811012724

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

Bin Wei ^a,^*

PMCID: PMC3089367 PMID: 21754508

Abstract

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)°.

Related literature

For background to tetrazoles, see: Hang et al. (2009 ▶). For our investigation of tetrazole compounds and their coordination modes, see: Xiong et al. (2002 ▶). For the preparation of tetrazoles using in situ synthesis of tetrazole through cycloaddition between organotin azide and organic cyano groups, see: Chen et al. (2010 ▶); Ye et al. (2006 ▶).

Experimental

Crystal data

C₂₃H₁₆N₂O
M _r = 336.38
Orthorhombic,
a = 14.526 (4) Å
b = 8.957 (3) Å
c = 27.126 (8) Å
V = 3529.3 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T _min = 0.842, T _max = 1.000
36455 measured reflections
4036 independent reflections
2865 reflections with I > 2σ(I)
R _int = 0.073

Refinement

R[F ² > 2σ(F ²)] = 0.082
wR(F ²) = 0.222
S = 1.24
4036 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012724/jh2278sup1.cif

e-67-o1209-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012724/jh2278Isup2.hkl

e-67-o1209-Isup2.hkl^{(201.9KB, hkl)}

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

Acknowledgments

The author is grateful to the starter fund of Southeast University for the purchase of the diffractometer.

supplementary crystallographic information

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.