rac-3,3,3-Trifluoro-lactic acid.

THE TITLE COMPOUND (SYSTEMATIC NAME: rac-3,3,3-trifluoro-2-hy-droxy-propanoic acid), C3H3F3O3, is a fluorinated derivative of lactic acid. The O=C-C-O(H) torsion angle is 13.26 (15)°. In the crystal, O-H⋯O hydrogen bonds and C-H⋯O contacts connect the mol-ecules into sheets perpendicular to the c axis.

Related literature

For the crystal structure of 2-hy­droxy-2-(trifluoro­meth­yl)proprionic acid, see: Soloshonok et al. (2007 ▶). For background to chelate ligands, see: Gade (1998 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C3H3F3O3

M = 144.05

Orthorhombic,

a = 10.586 (3) Å

b = 9.248 (3) Å

c = 10.826 (3) Å

V = 1059.9 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 200 K

0.40 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.892, T max = 1.000

9450 measured reflections

1309 independent reflections

1133 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.06

1309 reflections

82 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813003097/zl2532sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003097/zl2532Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003097/zl2532Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003097/zl2532Isup4.cml

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

C3H3F3O3	F(000) = 576
Mr = 144.05	Dx = 1.806 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4117 reflections
a = 10.586 (3) Å	θ = 3.5–28.2°
b = 9.248 (3) Å	µ = 0.22 mm−1
c = 10.826 (3) Å	T = 200 K
V = 1059.9 (5) Å3	Platelet, colourless
Z = 8	0.40 × 0.30 × 0.25 mm

Bruker APEXII CCD diffractometer	1309 independent reflections
Radiation source: fine-focus sealed tube	1133 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 28.3°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→10
Tmin = 0.892, Tmax = 1.000	k = −12→12
9450 measured reflections	l = −14→14

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0349P)2 + 0.3452P] where P = (Fo2 + 2Fc2)/3
1309 reflections	(Δ/σ)max < 0.001
82 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
F1	0.07491 (11)	0.07334 (11)	0.26362 (9)	0.0698 (3)
F2	0.24046 (9)	0.20543 (13)	0.26938 (9)	0.0670 (3)
F3	0.06121 (11)	0.29936 (12)	0.22550 (8)	0.0661 (3)
O3	0.16058 (7)	0.35907 (8)	0.46617 (9)	0.0346 (2)
H12	0.1084	0.4270	0.4731	0.052*
O1	−0.10270 (7)	0.12077 (8)	0.45966 (9)	0.0361 (2)
H111	−0.1790	0.1327	0.4782	0.054*
O2	−0.09203 (7)	0.35985 (8)	0.48706 (9)	0.0348 (2)
C1	−0.04410 (10)	0.24515 (11)	0.46318 (10)	0.0256 (2)
C2	0.09691 (10)	0.23181 (11)	0.43390 (10)	0.0260 (2)
H12A	0.1328	0.1499	0.4829	0.031*
C3	0.11835 (13)	0.20173 (15)	0.29671 (12)	0.0398 (3)

	U11	U22	U33	U12	U13	U23
F1	0.0956 (8)	0.0594 (6)	0.0543 (6)	−0.0146 (5)	0.0143 (5)	−0.0292 (5)
F2	0.0451 (5)	0.1003 (8)	0.0556 (5)	0.0055 (5)	0.0226 (4)	−0.0110 (5)
F3	0.0827 (7)	0.0809 (7)	0.0348 (5)	0.0224 (6)	0.0003 (4)	0.0123 (4)
O3	0.0212 (4)	0.0258 (4)	0.0568 (5)	0.0024 (3)	−0.0003 (3)	−0.0067 (4)
O1	0.0232 (4)	0.0251 (4)	0.0600 (6)	0.0008 (3)	0.0000 (4)	−0.0019 (4)
O2	0.0271 (4)	0.0252 (4)	0.0523 (5)	0.0034 (3)	0.0029 (4)	−0.0034 (3)
C1	0.0227 (5)	0.0257 (5)	0.0285 (5)	0.0020 (4)	−0.0023 (4)	0.0008 (4)
C2	0.0229 (5)	0.0237 (5)	0.0315 (5)	0.0026 (4)	−0.0003 (4)	−0.0006 (4)
C3	0.0393 (7)	0.0437 (7)	0.0362 (6)	0.0038 (5)	0.0053 (5)	−0.0030 (5)

F1—C3	1.3227 (17)	O1—H111	0.8399
F2—C3	1.3265 (17)	O2—C1	1.2040 (13)
F3—C3	1.3325 (17)	C1—C2	1.5310 (15)
O3—C2	1.4005 (13)	C2—C3	1.5280 (17)
O3—H12	0.8400	C2—H12A	1.0000
O1—C1	1.3074 (13)
C2—O3—H12	109.5	C3—C2—H12A	108.8
C1—O1—H111	109.5	C1—C2—H12A	108.8
O2—C1—O1	125.56 (10)	F1—C3—F2	107.55 (12)
O2—C1—C2	121.76 (10)	F1—C3—F3	107.08 (12)
O1—C1—C2	112.68 (9)	F2—C3—F3	107.21 (12)
O3—C2—C3	108.91 (10)	F1—C3—C2	112.03 (11)
O3—C2—C1	110.48 (8)	F2—C3—C2	110.91 (11)
C3—C2—C1	111.15 (9)	F3—C3—C2	111.81 (11)
O3—C2—H12A	108.8
O2—C1—C2—O3	13.26 (15)	C1—C2—C3—F1	−66.42 (14)
O1—C1—C2—O3	−166.37 (9)	O3—C2—C3—F2	51.46 (14)
O2—C1—C2—C3	−107.76 (12)	C1—C2—C3—F2	173.40 (11)
O1—C1—C2—C3	72.61 (12)	O3—C2—C3—F3	−68.14 (13)
O3—C2—C3—F1	171.65 (10)	C1—C2—C3—F3	53.80 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H12···O2i	0.84	2.03	2.7459 (13)	143
O1—H111···O3ii	0.84	1.80	2.6381 (13)	172
C2—H12A···O1iii	1.00	2.60	3.4588 (16)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H12⋯O2i	0.84	2.03	2.7459 (13)	143
O1—H111⋯O3ii	0.84	1.80	2.6381 (13)	172
C2—H12A⋯O1iii	1.00	2.60	3.4588 (16)	144

Symmetry codes: (i) ; (ii) ; (iii) .