[Journal logo]

Volume 67 
Part 5 
Page o1054  
May 2011  

Received 24 March 2011
Accepted 29 March 2011
Online 7 April 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.048
wR = 0.151
Data-to-parameter ratio = 10.8
Details
Open access

A new polymorph of 2,6-bis(trifluoromethyl)benzoic acid

aThe Maritimes Centre for Green Chemistry and the Department of Chemistry, Saint Mary's University, 923 Robie Street, Halifax, NS B3H 3C3, Canada
Correspondence e-mail: jason.masuda@smu.ca

The asymmetric unit of a second polymorph of the title compound, C9H4F6O2, contains five independent molecules, which form hydrogen-bonded O-H...O dimers about inversion centers. The most significant structural difference between this structure and that of the first polymorph [Tobin & Masuda (2009[Tobin, J. M. & Masuda, J. D. (2009). Acta Cryst. E65, o1217.]). Acta Cryst. E65, o1217] is the hydrogen-bonded, dimeric orientation of the carboxylic acid functionalities.

Related literature

For the first polymorph of the title compound, see: Tobin & Masuda (2009[Tobin, J. M. & Masuda, J. D. (2009). Acta Cryst. E65, o1217.]). For details of the synthesis, see: Dmowski & Piasecka-Macieiewska (1998)[Dmowski, W. & Piasecka-Macieiewska, K. (1998). Tetrahedron, 54, 6781-6792.]. For information on dimeric versus catemeric crystal growth in benzoic acids, see: Moorthy et al. (2002[Moorthy, J. N., Natarajan, R., Mal, P. & Venugopalan, P. (2002). J. Am. Chem. Soc. 124, 6530-6531.]).

[Scheme 1]

Experimental

Crystal data
  • C9H4F6O2

  • Mr = 258.12

  • Triclinic, [P \overline 1]

  • a = 10.312 (2) Å

  • b = 11.243 (2) Å

  • c = 21.283 (4) Å

  • [alpha] = 79.565 (3)°

  • [beta] = 88.961 (3)°

  • [gamma] = 85.125 (3)°

  • V = 2418.0 (9) Å3

  • Z = 10

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 100 K

  • 0.14 × 0.11 × 0.11 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.980

  • 16341 measured reflections

  • 8352 independent reflections

  • 5092 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.151

  • S = 0.85

  • 8352 reflections

  • 771 parameters

  • 6 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1i 0.84 1.87 2.701 (4) 172
O4-H4A...O10ii 0.84 1.82 2.657 (3) 174
O6-H6A...O8i 0.84 1.84 2.673 (4) 170
O7-H7...O5i 0.84 1.80 2.638 (4) 173
O9-H9...O3iii 0.84 1.81 2.644 (3) 174
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2403 ).


Acknowledgements

The authors would like to thank the Natural Sciences and Engineering Research Council for a Discovery Grant and a Research Tools and Instruments Grant (JDM), the Canadian Foundation for Innovation for a Leaders Opportunity Fund Grant and the Nova Scotia Research and Innovation Trust (JDM).

References

Bruker (2010). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dmowski, W. & Piasecka-Macieiewska, K. (1998). Tetrahedron, 54, 6781-6792.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Moorthy, J. N., Natarajan, R., Mal, P. & Venugopalan, P. (2002). J. Am. Chem. Soc. 124, 6530-6531.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tobin, J. M. & Masuda, J. D. (2009). Acta Cryst. E65, o1217.  [CSD] [CrossRef] [details]


Acta Cryst (2011). E67, o1054  [ doi:10.1107/S1600536811011731 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.