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

Guan, J.-N.; Kong, X.-J.; Xu, B.; Liang, J.-H.; Song, N.

doi:10.1107/S1600536809010125

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o844

doi:10.1107/S1600536809010125

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

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

^aCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: guanjn@sina.com

(Received 16 March 2009; accepted 19 March 2009; online 25 March 2009)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.068
wR(F²) = 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

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
Symmetry code: (i) -x+1, -y, -z+2.

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.

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level.
	Fig. 2. View of the packing and hydrogen bonding interactions of (I).

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

Crystal data top

C₁₀H₉F₃O₂	Z = 2
M_r = 218.17	F(000) = 224
Triclinic, P1	D_x = 1.481 Mg m⁻³
Hall symbol: -P 1	Melting point: 379 K
a = 7.9028 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.288 (2) Å	Cell parameters from 25 reflections
c = 9.238 (3) Å	θ = 9–12°
α = 63.381 (15)°	µ = 0.14 mm⁻¹
β = 85.20 (3)°	T = 298 K
γ = 65.70 (2)°	Yellow, colourless
V = 489.2 (2) Å³	0.20 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	874 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.017
Graphite monochromator	θ_max = 25.3°, θ_min = 2.5°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
T_min = 0.973, T_max = 0.986	l = −11→11
1894 measured reflections	3 standard reflections every 200 reflections
1754 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.178	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.06P)² + 0.216P] where P = (F_o² + 2F_c²)/3
1754 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₀H₉F₃O₂	γ = 65.70 (2)°
M_r = 218.17	V = 489.2 (2) Å³
Triclinic, P1	Z = 2
a = 7.9028 (19) Å	Mo Kα radiation
b = 8.288 (2) Å	µ = 0.14 mm⁻¹
c = 9.238 (3) Å	T = 298 K
α = 63.381 (15)°	0.20 × 0.10 × 0.10 mm
β = 85.20 (3)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.00	Δρ_max = 0.19 e Å⁻³
1754 reflections	Δρ_min = −0.17 e Å⁻³
128 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.7456 (3)	−0.0616 (4)	1.0251 (3)	0.0961 (9)
H1A	0.6554	−0.0765	1.0699	0.144*
O2	0.5346 (4)	0.1263 (4)	0.8086 (3)	0.0888 (9)
F1	1.5281 (8)	0.2427 (10)	0.2421 (7)	0.1096 (8)	0.429 (2)
F2	1.3838 (9)	0.5350 (11)	0.1735 (8)	0.1096 (8)	0.429 (2)
F3	1.3223 (9)	0.3992 (11)	0.0426 (8)	0.1096 (8)	0.429 (2)
F1'	1.4156 (7)	0.2852 (8)	0.1174 (6)	0.1096 (8)	0.571 (2)
F2'	1.4908 (7)	0.3848 (8)	0.2634 (6)	0.1096 (8)	0.571 (2)
F3'	1.2747 (6)	0.5871 (7)	0.0624 (6)	0.1096 (8)	0.571 (2)
C1	1.3412 (7)	0.3971 (8)	0.1896 (6)	0.1096 (8)
C2	1.2089 (5)	0.3532 (5)	0.2963 (4)	0.0649 (9)
C3	1.0233 (5)	0.4424 (6)	0.2356 (5)	0.0865 (12)
H3A	0.9861	0.5349	0.1262	0.104*
C4	0.8919 (5)	0.3987 (6)	0.3320 (5)	0.0906 (13)
H4A	0.7682	0.4591	0.2857	0.109*
C5	0.9377 (5)	0.2676 (5)	0.4958 (4)	0.0628 (9)
C6	1.1224 (5)	0.1850 (7)	0.5566 (5)	0.0921 (13)
H6A	1.1592	0.0968	0.6670	0.111*
C7	1.2561 (5)	0.2288 (6)	0.4585 (4)	0.0827 (12)
H7A	1.3794	0.1723	0.5046	0.099*
C8	0.7910 (5)	0.2231 (6)	0.5981 (4)	0.0780 (11)
H8A	0.7335	0.1714	0.5508	0.094*
H8B	0.6948	0.3479	0.5891	0.094*
C9	0.8489 (5)	0.0810 (5)	0.7754 (4)	0.0756 (11)
H9A	0.9393	−0.0470	0.7859	0.091*
H9B	0.9113	0.1283	0.8231	0.091*
C10	0.6946 (6)	0.0527 (6)	0.8697 (5)	0.0716 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0801 (18)	0.104 (2)	0.0801 (18)	−0.0392 (16)	0.0072 (14)	−0.0214 (16)
O2	0.0765 (18)	0.100 (2)	0.0808 (17)	−0.0409 (16)	0.0095 (14)	−0.0300 (15)
F1	0.1028 (18)	0.119 (2)	0.1119 (18)	−0.0560 (17)	0.0344 (13)	−0.0514 (15)
F2	0.1028 (18)	0.119 (2)	0.1119 (18)	−0.0560 (17)	0.0344 (13)	−0.0514 (15)
F3	0.1028 (18)	0.119 (2)	0.1119 (18)	−0.0560 (17)	0.0344 (13)	−0.0514 (15)
F1'	0.1028 (18)	0.119 (2)	0.1119 (18)	−0.0560 (17)	0.0344 (13)	−0.0514 (15)
F2'	0.1028 (18)	0.119 (2)	0.1119 (18)	−0.0560 (17)	0.0344 (13)	−0.0514 (15)
F3'	0.1028 (18)	0.119 (2)	0.1119 (18)	−0.0560 (17)	0.0344 (13)	−0.0514 (15)
C1	0.1028 (18)	0.119 (2)	0.1119 (18)	−0.0560 (17)	0.0344 (13)	−0.0514 (15)
C2	0.075 (2)	0.060 (2)	0.073 (2)	−0.032 (2)	0.0156 (18)	−0.0384 (19)
C3	0.074 (3)	0.085 (3)	0.074 (2)	−0.025 (2)	0.004 (2)	−0.021 (2)
C4	0.064 (2)	0.095 (3)	0.088 (3)	−0.025 (2)	0.007 (2)	−0.029 (2)
C5	0.067 (2)	0.064 (2)	0.067 (2)	−0.0261 (18)	0.0045 (17)	−0.0388 (18)
C6	0.080 (3)	0.108 (3)	0.071 (2)	−0.042 (3)	0.003 (2)	−0.023 (2)
C7	0.073 (2)	0.108 (3)	0.073 (2)	−0.045 (2)	0.0032 (19)	−0.039 (2)
C8	0.069 (2)	0.102 (3)	0.070 (2)	−0.039 (2)	0.0010 (18)	−0.042 (2)
C9	0.079 (2)	0.067 (2)	0.082 (2)	−0.030 (2)	0.016 (2)	−0.037 (2)
C10	0.081 (3)	0.069 (3)	0.082 (3)	−0.040 (2)	0.016 (2)	−0.042 (2)

Geometric parameters (Å, º) top

O1—C10	1.298 (4)	C4—C5	1.377 (5)
O1—H1A	0.8200	C4—H4A	0.9300
O2—C10	1.211 (4)	C5—C6	1.373 (5)
F1—C1	1.436 (8)	C5—C8	1.493 (5)
F2—C1	1.264 (8)	C6—C7	1.389 (5)
F3—C1	1.371 (8)	C6—H6A	0.9300
F1'—C1	1.300 (6)	C7—H7A	0.9300
F2'—C1	1.359 (6)	C8—C9	1.494 (5)
F3'—C1	1.379 (6)	C8—H8A	0.9700
C1—C2	1.420 (5)	C8—H8B	0.9700
C2—C7	1.357 (4)	C9—C10	1.475 (5)
C2—C3	1.373 (5)	C9—H9A	0.9700
C3—C4	1.367 (5)	C9—H9B	0.9700
C3—H3A	0.9300

C10—O1—H1A	109.5	C3—C4—C5	121.8 (4)
F2—C1—F1'	124.1 (5)	C3—C4—H4A	119.1
F2—C1—F2'	50.9 (4)	C5—C4—H4A	119.1
F1'—C1—F2'	104.0 (5)	C6—C5—C4	116.1 (4)
F2—C1—F3	111.3 (5)	C6—C5—C8	123.3 (3)
F1'—C1—F3	40.0 (3)	C4—C5—C8	120.6 (3)
F2'—C1—F3	128.7 (5)	C5—C6—C7	122.1 (4)
F2—C1—F3'	53.5 (4)	C5—C6—H6A	119.0
F1'—C1—F3'	103.4 (5)	C7—C6—H6A	119.0
F2'—C1—F3'	102.5 (5)	C2—C7—C6	120.7 (4)
F3—C1—F3'	68.0 (4)	C2—C7—H7A	119.6
F2—C1—C2	119.6 (5)	C6—C7—H7A	119.6
F1'—C1—C2	116.3 (5)	C5—C8—C9	118.1 (3)
F2'—C1—C2	113.8 (4)	C5—C8—H8A	107.8
F3—C1—C2	115.5 (5)	C9—C8—H8A	107.8
F3'—C1—C2	115.2 (4)	C5—C8—H8B	107.8
F2—C1—F1	96.1 (5)	C9—C8—H8B	107.8
F1'—C1—F1	58.3 (4)	H8A—C8—H8B	107.1
F2'—C1—F1	50.5 (3)	C10—C9—C8	114.8 (3)
F3—C1—F1	95.9 (5)	C10—C9—H9A	108.6
F3'—C1—F1	130.2 (4)	C8—C9—H9A	108.6
C2—C1—F1	114.2 (4)	C10—C9—H9B	108.6
C7—C2—C3	117.5 (3)	C8—C9—H9B	108.6
C7—C2—C1	123.0 (4)	H9A—C9—H9B	107.5
C3—C2—C1	119.5 (4)	O2—C10—O1	122.4 (3)
C4—C3—C2	121.6 (4)	O2—C10—C9	123.5 (4)
C4—C3—H3A	119.2	O1—C10—C9	114.0 (4)
C2—C3—H3A	119.2

F2—C1—C2—C7	−85.8 (7)	C2—C3—C4—C5	2.0 (7)
F1'—C1—C2—C7	92.3 (6)	C3—C4—C5—C6	0.5 (6)
F2'—C1—C2—C7	−28.5 (7)	C3—C4—C5—C8	179.9 (4)
F3—C1—C2—C7	137.0 (5)	C4—C5—C6—C7	−0.7 (6)
F3'—C1—C2—C7	−146.5 (5)	C8—C5—C6—C7	179.9 (4)
F1—C1—C2—C7	27.1 (7)	C3—C2—C7—C6	3.8 (6)
F2—C1—C2—C3	92.8 (7)	C1—C2—C7—C6	−177.6 (4)
F1'—C1—C2—C3	−89.2 (6)	C5—C6—C7—C2	−1.5 (7)
F2'—C1—C2—C3	150.0 (5)	C6—C5—C8—C9	−0.1 (5)
F3—C1—C2—C3	−44.4 (7)	C4—C5—C8—C9	−179.5 (4)
F3'—C1—C2—C3	32.0 (7)	C5—C8—C9—C10	177.0 (3)
F1—C1—C2—C3	−154.3 (5)	C8—C9—C10—O2	5.0 (5)
C7—C2—C3—C4	−4.1 (6)	C8—C9—C10—O1	−176.0 (3)
C1—C2—C3—C4	177.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.82	1.87	2.687 (4)	174

Symmetry code: (i) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₀H₉F₃O₂
M_r	218.17
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.9028 (19), 8.288 (2), 9.238 (3)
α, β, γ (°)	63.381 (15), 85.20 (3), 65.70 (2)
V (Å³)	489.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.973, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	1894, 1754, 874
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.178, 1.00
No. of reflections	1754
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.82	1.87	2.687 (4)	174

Symmetry code: (i) −x+1, −y, −z+2.

Acknowledgements

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Battistuzzi, G., Cacchi, S., Fabrizi, G. & Bernini, R. (2003). Synlett, pp. 1133–1136. Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Feuerstein, M., Berthiol, F., Doucet, H. & Santelli, M. (2003). Org. Biomol. Chem. pp. 2235–2237. Web of Science CrossRef Google Scholar
Feuerstein, M., Laurenti, D., Bougeant, C., Doucet, H. & Santelli, M. (2001). Chem. Commun. pp. 325–326. Web of Science CrossRef Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Johnson, P. Y. & Wen, J. Q. (1981). J. Org. Chem. 46, 2767–2771. CrossRef CAS Web of Science Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shoda, K. & Kuriyama, H. (2003). PCT Int. Appl. WO, 2003 070 686. Google Scholar
Yamanouchi, T. & Yamane, H. (1988). Jpn Patent JP 63 250 356. Google Scholar