4-(6-Quinolyl­oxymeth­yl)benzonitrile

Min Min Zhao; Yong Hua Li; De Hong Wu; Qing Wan

doi:10.1107/S1600536809016560

. 2009 May 14;65(Pt 6):o1261. doi: 10.1107/S1600536809016560

4-(6-Quinolyloxymethyl)benzonitrile

Min Min Zhao ^a, Yong Hua Li ^a,^*, De Hong Wu ^a, Qing Wan ^a

PMCID: PMC2969587 PMID: 21583126

Abstract

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.

Related literature

For general background to nitrile compounds, see: Jin et al. (1994 ▶); Brewis et al. (2003 ▶). For related structures, see: Fu & Zhao (2007 ▶); Zhao (2008 ▶).

Experimental

Crystal data

C₁₇H₁₂N₂O
M _r = 260.29
Monoclinic,
a = 9.466 (2) Å
b = 13.078 (3) Å
c = 10.857 (2) Å
β = 90.81 (3)°
V = 1343.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.26 × 0.24 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.976, T _max = 0.981
12007 measured reflections
2622 independent reflections
1956 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.120
S = 1.06
2622 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016560/lx2099sup1.cif

e-65-o1261-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016560/lx2099Isup2.hkl

e-65-o1261-Isup2.hkl^{(128.8KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cgⁱ	0.93	2.83	3.613 (2)	142
C13—H13⋯N1ⁱⁱ	0.93	2.60	3.398 (2)	145

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Symmetry codes: (i) Inline graphic ; (ii) . Cg is the centroid of the C1–C4/C8/C9 benzene ring.

Acknowledgments

This work was supported by a Start-up Grant (No. 4007041028) and a Science Technology Grant (No. KJ2009375) from Southeast University to YHL.

supplementary crystallographic information

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···Cgⁱ 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.