3-[4-(Trifluoro-meth-yl)phen-yl]propanoic acid.

In crystal of the the title compound, C(10)H(9)F(3)O(2), 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 = 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

Δρmax = 0.19 e Å−3

Δρmin = −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.

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

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

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

C10H9F3O2	Z = 2
Mr = 218.17	F(000) = 224
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.06P)2 + 0.216P] where P = (Fo2 + 2Fc2)/3
1754 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) .