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Volume 69 
Part 3 
Page o335  
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) = 0.003 Å
R = 0.029
wR = 0.076
Data-to-parameter ratio = 8.8
Details
Open access

3,3,3-Trifluoro-2-hydroxy-2-(trifluoromethyl)propionic 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

In the title perfluorinated hydroxyisobutyric acid derivative, C4H2F6O3, the molecule shows approximately Cs symmetry. The carboxy group is nearly coplanar with the C-OH moiety and the O=C-C-O(H) torsion angle is 5.5 (2)°. An intramolecular O-H...O hydrogen bond occurs. In the crystal, O-H...O hydrogen bonds connect the molecules into supramolecular chains along the a-axis direction.

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
  • C4H2F6O3

  • Mr = 212.06

  • Orthorhombic, P 21 21 21

  • a = 5.9949 (2) Å

  • b = 6.4007 (2) Å

  • c = 18.5642 (6) Å

  • V = 712.34 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 200 K

  • 0.53 × 0.53 × 0.34 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.908, Tmax = 1.000

  • 3824 measured reflections

  • 1052 independent reflections

  • 1024 reflections with I > 2[sigma](I)

  • Rint = 0.010

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.076

  • S = 1.05

  • 1052 reflections

  • 120 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O2 0.84 2.13 2.6274 (17) 118
O1-H1...O3i 0.84 1.91 2.7170 (17) 160
O3-H3...O2ii 0.84 2.06 2.7186 (17) 135
Symmetry codes: (i) x-1, y, z; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z].

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: TK5193 ).


Acknowledgements

The authors thank Mr Jamie Haner 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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o335  [ doi:10.1107/S1600536813003103 ]

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