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Volume 69 
Part 1 
Page o30  
January 2013  

Received 25 November 2012
Accepted 2 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.052
wR = 0.132
Data-to-parameter ratio = 11.8
Details
Open access

3-Chloro-2,4,5-trifluorobenzoic acid

aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China, and bChemical Engineering Department, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China
Correspondence e-mail: njutshs@126.com

The title compound, C7H2ClF3O2, was prepared by the chlorination of 3-amino-2,4,5-trifluorobenzoic acid. The carboxyl group is twisted relative to the benzene ring by 6.8 (1)°. In the crystal, pairs of O-H...O hydrogen bonds link molecules into typical centrosymmetric carboxylic acid dimers. These dimers are arranged into sheets parallel to (-103).

Related literature

For applications of the title compound in synthesis, see: Sun et al. (2011[Sun, H., Jiang, L., Li, Y.-L., Lu, X. & Xu, H. (2011). Acta Cryst. E67, o2974.]). For a related structure, see: Zhu (2009[Zhu, X. (2009). Acta Cryst. E65, o1886.]).

[Scheme 1]

Experimental

Crystal data
  • C7H2ClF3O2

  • Mr = 210.54

  • Monoclinic, P 21 /n

  • a = 4.4760 (9) Å

  • b = 13.654 (3) Å

  • c = 12.400 (3) Å

  • [beta] = 97.16 (3)°

  • V = 751.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.52 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.859, Tmax = 0.950

  • 1578 measured reflections

  • 1394 independent reflections

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

  • Rint = 0.092

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.132

  • S = 1.00

  • 1394 reflections

  • 118 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2A...O1i 0.82 1.84 2.658 (4) 178
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2539 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sun, H., Jiang, L., Li, Y.-L., Lu, X. & Xu, H. (2011). Acta Cryst. E67, o2974.  [CSD] [CrossRef] [details]
Zhu, X. (2009). Acta Cryst. E65, o1886.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o30  [ doi:10.1107/S1600536812049446 ]

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