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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 [sigma](C-C) = 0.002 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 16.0
Details
Open access

rac-3,3,3-Trifluorolactic acid

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-H...O hydrogen bonds and C-H...O 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[Soloshonok, V. A., Ueki, H., Yasumoto, M., Mekala, S., Hirschi, J. S. & Singleton, D. A. (2007). J. Am. Chem. Soc. 129, 12112-12113.]). For background to chelate ligands, see: Gade (1998[Gade, L. H. (1998). Koordinationschemie, 1. Auflage, Weinheim: Wiley-VCH.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C3H3F3O3

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.892, Tmax = 1.000

  • 9450 measured reflections

  • 1309 independent reflections

  • 1133 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.081

  • S = 1.06

  • 1309 reflections

  • 82 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

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) -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[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[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.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [CrossRef] [ChemPort] [ISI]
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.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Soloshonok, V. A., Ueki, H., Yasumoto, M., Mekala, S., Hirschi, J. S. & Singleton, D. A. (2007). J. Am. Chem. Soc. 129, 12112-12113.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o336  [ doi:10.1107/S1600536813003097 ]

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