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Volume 69 
Part 10 
Page o1519  
October 2013  

Received 17 July 2013
Accepted 2 September 2013
Online 7 September 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.031
wR = 0.104
Data-to-parameter ratio = 16.6
Details
Open access

2,3,4,5,6-Pentafluoro-trans-cinnamic acid

aCentro de Graduados e Investigación del Instituto Tecnológico de Tijuana, Apdo. Postal 1166, 22500, Tijuana, B.C., Mexico
Correspondence e-mail: gaguirre777@gmail.com

The title compound, C9H3F5O2, crystallizes as O-H...O hydrogen-bonded carboxylic acid dimers that, together with C-H...F interactions and O...F [2.8065 (13) and 2.9628 (13) Å] and F...F [2.6665 (11), 2.7049 (12) and 2.7314 (12) Å] contacts, form a sheet-like structure. The sheets are stacked via short [pi]-[pi] interactions [centroid-centroid distance = 4.3198 (11) Å]. An intramolecular C-H...F interaction is also observed.

Related literature

For related structures, see: Goud et al. (1995[Goud, B. S., Reddy, P. K., Panneerselvam, K. & Desiraju, G. R. (1995). Acta Cryst. C51, 683-685.]); Quan & Sun, (2013[Quan, J. & Sun, H.-S. (2013). Acta Cryst. E69, o30.]). For the biological activity of N-alkenyl amides, see: Brettle & Mosedale (1988[Brettle, R. & Mosedale, A. J. (1988). J. Chem. Soc. Perkin Trans. 1, pp. 2185-2195.]). For fluorinated N-alkenyl amides, see: Aguirre et al. (1998[Aguirre, G., Somanathan, R. & Hellberg, L. H. (1998). J. Fluorine Chem. 90, 5-8.]).

[Scheme 1]

Experimental

Crystal data
  • C9H3F5O2

  • Mr = 238.11

  • Triclinic, [P \overline 1]

  • a = 4.3198 (9) Å

  • b = 7.4921 (17) Å

  • c = 13.225 (3) Å

  • [alpha] = 93.612 (12)°

  • [beta] = 93.912 (12)°

  • [gamma] = 103.769 (12)°

  • V = 413.37 (15) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 100 K

  • 0.35 × 0.30 × 0.09 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.931, Tmax = 0.982

  • 11089 measured reflections

  • 2405 independent reflections

  • 2000 reflections with I > 2[sigma](I)

  • Rint = 0.026

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

  • wR(F2) = 0.104

  • S = 0.70

  • 2405 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.50 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2A...O1i 0.84 1.81 2.6485 (13) 179
C7-H7...F4ii 0.95 2.47 3.4074 (14) 169
C8-H8...F5 0.95 2.22 2.8434 (14) 123
Symmetry codes: (i) -x+1, -y+3, -z+1; (ii) x+1, y+1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2124 ).


Acknowledgements

We gratefully acknowledge support for this project from the Dirección General de Educación Superior Tecnológica (DGEST) 2536.09-P.

References

Aguirre, G., Somanathan, R. & Hellberg, L. H. (1998). J. Fluorine Chem. 90, 5-8.  [Web of Science] [CrossRef] [ChemPort]
Brettle, R. & Mosedale, A. J. (1988). J. Chem. Soc. Perkin Trans. 1, pp. 2185-2195.  [CrossRef]
Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Goud, B. S., Reddy, P. K., Panneerselvam, K. & Desiraju, G. R. (1995). Acta Cryst. C51, 683-685.  [CSD] [CrossRef] [IUCr Journals]
Quan, J. & Sun, H.-S. (2013). Acta Cryst. E69, o30.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1519  [ doi:10.1107/S1600536813024513 ]

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