3-[4-(Trifluoro­meth­yl)phen­yl]propanoic acid

Jian-Ning Guan; Xiang-Jun Kong; Bin Xu; Jin-Hua Liang; Na Song

doi:10.1107/S1600536809010125

. 2009 Mar 25;65(Pt 4):o844. doi: 10.1107/S1600536809010125

3-[4-(Trifluoromethyl)phenyl]propanoic acid

Jian-Ning Guan ^a,^*, Xiang-Jun Kong ^a, Bin Xu ^a, Jin-Hua Liang ^a, Na Song ^a

PMCID: PMC2969077 PMID: 21582563

Abstract

In crystal of the the title compound, C₁₀H₉F₃O₂, inversion dimers linked by pairs of O—H⋯O hydrogen bonds occur.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related literature on acid derivatives, see: Battistuzzi et al. (2003 ▶); Feuerstein et al. (2001 ▶, 2003 ▶); Johnson & Wen (1981 ▶); Shoda & Kuriyama (2003 ▶); Yamanouchi & Yamane (1988 ▶).

Experimental

Crystal data

C₁₀H₉F₃O₂
M _r = 218.17
Triclinic,
a = 7.9028 (19) Å
b = 8.288 (2) Å
c = 9.238 (3) Å
α = 63.381 (15)°
β = 85.20 (3)°
γ = 65.70 (2)°
V = 489.2 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 298 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.973, T _max = 0.986
1894 measured reflections
1754 independent reflections
874 reflections with I > 2σ(I)
R _int = 0.017
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.178
S = 1.00
1754 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; 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: SHELXL97; software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010125/at2744sup1.cif

e-65-0o844-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010125/at2744Isup2.hkl

e-65-0o844-Isup2.hkl^{(86.4KB, 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
O1—H1A⋯O2ⁱ	0.82	1.87	2.687 (4)	174

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

Some derivatives of acids is important chemical material (Battistuzzi et al., 2003; Feuerstein et al., 2003, 2001; Johnson & Wen, 1981; Yamanouchi & Yamane 1988; Shoda & Kuriyama, 2003). We report here the crystal structure of the title compound, (I). The molecular structure of (I) is shown in Fig. 1, and the selected geometric parameters are given in Table 1. The bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987).

In the crystal of the title compound, there is an intermolecular O—H···O hydrogen bond which may be effective to the stabilization of the crystal.

Experimental

2,2-Dimethyl-5-(4-trifluoromethyl-benzyl)-[1,3]dioxane-4,6-dione (1 mmol), acetonitrile (25 ml) and water (0.25 ml) were mixed and subjected to microwave irradiation at 120° for 30 min (150 psi, 300 W, run time 5 min, hold time 30 min). Crude compound (I) was obtained. An X-ray grade crystal of (I) (500 mg) was grown from ethyl ether (10 ml) at room temperature.