rac-3,3,3-Trifluoro­lactic acid

Gerber, T.; Betz, R.

doi:10.1107/S1600536813003097

Volume 69
Part 3
Page o336
March 2013

Received 29 January 2013
Accepted 30 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 16.0
Details

rac-3,3,3-Trifluorolactic acid

Thomas Gerber ^a and Richard Betz ^a ^*

^aNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

The title compound (systematic name: rac-3,3,3-trifluoro-2-hydroxypropanoic 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-HO hydrogen bonds and C-HO contacts connect the molecules 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_r = 144.05
Orthorhombic, P b c a
a = 10.586 (3) Å
b = 9.248 (3) Å
c = 10.826 (3) Å
V = 1059.9 (5) Å³
Z = 8
Mo K radiation
= 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 > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.081
S = 1.06
1309 reflections
82 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H12O2ⁱ	0.84	2.03	2.7459 (13)	143
O1-H111O3ⁱⁱ	0.84	1.80	2.6381 (13)	172
C2-H12AO1ⁱⁱⁱ	1.00	2.60	3.4588 (16)	144
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) -x, -y, -z+1.

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).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2532 ).

Acknowledgements

The authors thank Mr Ulf Breddemann of McMaster University, Canada, for helpful discussions.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gade, L. H. (1998). Koordinationschemie, 1. Auflage, Weinheim: Wiley-VCH.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Soloshonok, V. A., Ueki, H., Yasumoto, M., Mekala, S., Hirschi, J. S. & Singleton, D. A. (2007). J. Am. Chem. Soc. 129, 12112-12113.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds