Methyl 2-{[2,8-bis­(trifluoro­meth­yl)quinolin-4-yl]­oxy}acetate

Zhi-Qiang Feng; Xiao-Li Yang; Yuan-Feng Ye; Huai-Qing Wang; Tao Dong

doi:10.1107/S1600536811000328

. 2011 Jan 12;67(Pt 2):o321. doi: 10.1107/S1600536811000328

Methyl 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl]oxy}acetate

Zhi-Qiang Feng ^a,^*, Xiao-Li Yang ^a, Yuan-Feng Ye ^a, Huai-Qing Wang ^a, Tao Dong ^a

PMCID: PMC3051653 PMID: 21523007

Abstract

In the crystal structure of the title compound, C₁₄H₉F₆NO₃, molecules are connected by intermolecular C—H⋯O hydrogen bonds. The best planes through the benzene and pyridyl rings make a dihedral angle of 1.59 (12)°.

Related literature

The title compound is an important organic synthesis intermediate. For the synthetic procedure, see: Lilienkampf et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₉F₆NO₃
M _r = 353.22
Monoclinic,
a = 4.6980 (9) Å
b = 20.549 (4) Å
c = 15.176 (3) Å
β = 95.74 (3)°
V = 1457.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.953, T _max = 0.984
3017 measured reflections
2676 independent reflections
1747 reflections with I > 2σ(I)
R _int = 0.019
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.146
S = 1.01
2676 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536811000328/vm2070sup1.cif

e-67-0o321-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000328/vm2070Isup2.hkl

e-67-0o321-Isup2.hkl^{(131.4KB, 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—H12B⋯O2ⁱ	0.97	2.54	3.448 (4)	156

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Natural Science Fund for Colleges and Universities in Jiangsu Province (09kjd150011). The authors thank the Center of Testing and Analysis, Nanjing University, for help with the data collection.

supplementary crystallographic information

Comment

The title compound, methyl 2-((2,8-bis(trifluoromethyl)quinolin-4-yl)oxy)acetate is an important intermediate for the synthesis of drugs (Lilienkampf et al., 2009). Here we report the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987).

The phenyl ring and pyridyl ring are nearly coplanar as indicated by the dihedral angle of 1.59 (12) ° between the best planes through both rings.

The molecules show C—H···O and C—H···F intermolecular and intramolecular hydrogen bonds (Table 1) resulting in a three dimensional network, which seems to be very effective in the stabilization of the crystal structure (Fig. 2).

Experimental

The title compound, (I) was prepared by a method reported in literature (Lilienkampf et al., 2009). The crystals were obtained by dissolving (I) (0.5 g, 1.42 mmol) in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 5 d.