3-Chloro-2,4,5-trifluoro­benzoic acid

Quan, J.; Sun, H.-S.

doi:10.1107/S1600536812049446

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 (C-C) = 0.006 Å
R = 0.052
wR = 0.132
Data-to-parameter ratio = 11.8
Details

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

Jing Quan ^a and Hong-Shun Sun ^b ^*

^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-HO 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). For a related structure, see: Zhu (2009).

Experimental

Crystal data

C₇H₂ClF₃O₂
M_r = 210.54
Monoclinic, P 2₁ /n
a = 4.4760 (9) Å
b = 13.654 (3) Å
c = 12.400 (3) Å
= 97.16 (3)°
V = 751.9 (3) Å³
Z = 4
Mo K radiation
= 0.52 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.859, T_max = 0.950
1578 measured reflections
1394 independent reflections
699 reflections with I > 2(I)
R_int = 0.092
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.132
S = 1.00
1394 reflections
118 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO1ⁱ	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); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); 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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sun, H., Jiang, L., Li, Y.-L., Lu, X. & Xu, H. (2011). Acta Cryst. E67, o2974.
Zhu, X. (2009). Acta Cryst. E65, o1886.

organic compounds