3-[2-Chloro-4-(trifluoro­meth­yl)phen­oxy]benzoic acid

Yan-Ju Liu; Jie Liu

doi:10.1107/S1600536811043479

. 2011 Oct 29;67(Pt 11):o3049. doi: 10.1107/S1600536811043479

3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid

Yan-Ju Liu ^a,^*, Jie Liu ^b

PMCID: PMC3247442 PMID: 22220060

Abstract

The asymmetric unit of the title compound, C₁₄H₈ClF₃O₃, comprises two independent molecules. The rings in each molecule are connected together via O—H⋯O hydrogen bonds to form classical hydrogen-bonded carboxylic acid dimers. The dihedral angles between the benzene rings are 80.7 (1) and 68.7 (1)°.

Related literature

For background on applications of the title compound, see: Brown et al. (1997 ▶). For the synthesis of the title compound, see: Johnson (1977 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₈ClF₃O₃
M _r = 316.66
Triclinic,
a = 7.3390 (15) Å
b = 7.6880 (15) Å
c = 24.113 (5) Å
α = 90.54 (3)°
β = 92.18 (3)°
γ = 94.23 (3)°
V = 1355.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.909, T _max = 0.968
5407 measured reflections
4984 independent reflections
2318 reflections with I > 2σ(I)
R _int = 0.044
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.167
S = 1.00
4984 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 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 datablock(s) I, global. DOI: 10.1107/S1600536811043479/vm2129sup1.cif

e-67-o3049-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043479/vm2129Isup2.hkl

e-67-o3049-Isup2.hkl^{(244.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811043479/vm2129Isup3.cml

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
O2—H2B⋯O6	0.82	1.79	2.599 (4)	168
O5—H5B⋯O3	0.82	1.82	2.629 (4)	170

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Acknowledgments

This work was supported by the Science and Technology Department, Henan Province (grant No. 102102310321) and the Doctoral Research Fund of Henan Chinese Medicine. The authors thank the Center of Testing and Analysis, Nanjing University for data collection.

supplementary crystallographic information

Comment

The title compound, 3-[2-chloro-4-(trifluoromethyl)phenoxy]benzoic acid is an important intermediate, which can be utilized to synthesize acifluorfen (Brown et al., 1997). Here we report the crystal structure of the title compound Fig. 1). The asymmetric unit contains two molecules with a similar conformation (rms deviation fitting 21 non-H atoms: 0.400 Å) .

Intermolecular O—H···O hydrogen bonds (Table 1, Fig. 2) result in the formation of carboxylic acid dimers. The bond lengths and angles are within normal ranges (Allen et al., 1987). The dihedral angles between the rings A(C1—C6), B(C8—C13), C(C15—C20), D(C22—C27) are: A/B = 80.7 (1)°, C/D = 68.7 (1)°. The O atoms O1 and O4 lie in the benzene ring planes A and B, and C and D, respectively.

Experimental

The title compound, (I) was prepared by the method of the Ullmann condensation reaction (Johnson, 1977). The crystals were obtained by dissolving (I) (0.2 g, 0.6 mmol) in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 5 d.