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Volume 65 
Part 11 
Page o2670  
November 2009  

Received 12 August 2009
Accepted 25 September 2009
Online 7 October 2009

Key indicators
Single-crystal X-ray study
T = 233 K
Mean [sigma](C-C) = 0.004 Å
R = 0.061
wR = 0.226
Data-to-parameter ratio = 14.4
Details
Open access

1,2,3-Trifluorobenzene

aInstitut für Anorganische Chemie der Universität, 45117 Essen, Germany, and bIndian Institute of Science, Bangalore 560 012, India
Correspondence e-mail: roland.boese@uni-due.de, gautam_desiraju@yahoo.com

In the title compound, C6H3F3, weak electrostatic and dispersive forces between C([delta]+)-F([delta]-) and H([delta]+)-C([delta]-) groups are at the borderline of the hydrogen-bond phenomenon and are poorly directional and further deformed in the presence of [pi]-[pi] stacking interactions. The molecule lies on a twofold rotation axis. In the crystal structure, one-dimensional tapes are formed via two antidromic C-H...F hydrogen bonds. These tapes are, in turn, connected into corrugated two-dimensional sheets by bifurcated C-H...F hydrogen bonds. Packing in the third dimension is furnished by [pi]-[pi] stacking interactions with a centroid-centroid distance of 3.6362 (14) Å.

Related literature

For C-H...F interactions, see: Althoff et al. (2006[Althoff, G., Ruiz, J., Rodriguez, V., Lopez, G., Perez, J. & Janiak, C. (2006). CrystEngComm, 8, 662-665.]); Bats et al. (2000[Bats, J. W., Parsch, J. & Engels, J. W. (2000). Acta Cryst. C56, 201-205.]); Choudhury et al. (2004[Choudhury, A. R., Nagarajan, K. & Guru Row, T. N. (2004). Acta Cryst. C60, o644-o647.]); D'Oria & Novoa (2008[D'Oria, E. & Novoa, J. J. (2008). CrystEngComm, 10, 423-436.]); Dunitz & Taylor (1997[Dunitz, J. D. & Taylor, R. (1997). Chem. Eur. J. 3, 89-98.]); Howard et al. (1996[Howard, J. A. K., Hoy, V. J., O'Hagan, D. & Smith, G. T. (1996). Tetrahedron, 38, 12613-12622.]); Müller et al. (2007[Müller, K., Faeh, C. & Diederich, F. (2007). Science, 317, 1881-1886.]); O'Hagan (2008[O'Hagan, D. (2008). Chem. Soc. Rev. 37, 308-319.]); Reichenbacher et al. (2005[Reichenbacher, K., Suss, H. I. & Hulliger, J. (2005). J. Chem. Soc. Rev. 34, 22-30.]); Weiss et al. (1997[Weiss, H. C., Boese, R., Smith, H. L. & Haley, M. M. (1997). Chem. Commun. pp. 2403-2404.]). For related crystal structures of several polyfluorinated benzenes, see: Thalladi et al. (1998[Thalladi, V. R., Weiss, H. C., Bläser, D., Boese, R., Nangia, A. & Desiraju, G. R. (1998). J. Am. Chem. Soc. 120, 8702-8710.]). For crystallization techniques, see: Boese & Nussbaumer (1994[Boese, R. & Nussbaumer, M. (1994). In Situ Crystallisation Techniques. In Organic Crystal Chemistry, edited by D. W. Jones, pp. 20-37. Oxford University Press.]).

[Scheme 1]

Experimental

Crystal data
  • C6H3F3

  • Mr = 132.08

  • Monoclinic, C 2/c

  • a = 7.4238 (19) Å

  • b = 11.590 (3) Å

  • c = 7.0473 (17) Å

  • [beta] = 112.783 (4)°

  • V = 559.1 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.16 mm-1

  • T = 233 K

  • 0.30 × 0.30 × 0.30 mm

Data collection
  • Siemens SMART three-axis goniometer with an APEXII area-detector system diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker; 2004[Bruker (2004). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.820, Tmax = 0.953

  • 1074 measured reflections

  • 634 independent reflections

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

  • Rint = 0.013

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.226

  • S = 1.04

  • 634 reflections

  • 44 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 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
C3-H3...F2i 1.10 2.77 3.560 (3) 129
C3-H3...F1ii 1.10 2.59 3.528 (4) 144
C4-H4...F2iii 1.00 2.60 3.440 (4) 142
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (iii) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: 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.]) and GIMP2 (The GIMP team, 2008[The GIMP team (2008). The GNU Image Manipulation Program, http://www.gimp.org.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2880 ).


Acknowledgements

MTK and RB thank the DFG FOR-618. GRD thanks the DST for the award of a J.C. Bose fellowship. TST thanks the UGC for an SRF.

References

Althoff, G., Ruiz, J., Rodriguez, V., Lopez, G., Perez, J. & Janiak, C. (2006). CrystEngComm, 8, 662-665.  [ISI] [CSD] [CrossRef] [ChemPort]
Bats, J. W., Parsch, J. & Engels, J. W. (2000). Acta Cryst. C56, 201-205.  [CSD] [CrossRef] [details]
Boese, R. & Nussbaumer, M. (1994). In Situ Crystallisation Techniques. In Organic Crystal Chemistry, edited by D. W. Jones, pp. 20-37. Oxford University Press.
Bruker (2004). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Choudhury, A. R., Nagarajan, K. & Guru Row, T. N. (2004). Acta Cryst. C60, o644-o647.  [CSD] [CrossRef] [ChemPort] [details]
D'Oria, E. & Novoa, J. J. (2008). CrystEngComm, 10, 423-436.  [ChemPort]
Dunitz, J. D. & Taylor, R. (1997). Chem. Eur. J. 3, 89-98.  [CrossRef] [ChemPort]
Howard, J. A. K., Hoy, V. J., O'Hagan, D. & Smith, G. T. (1996). Tetrahedron, 38, 12613-12622.  [CrossRef] [ISI]
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]
Müller, K., Faeh, C. & Diederich, F. (2007). Science, 317, 1881-1886.  [ISI] [PubMed]
O'Hagan, D. (2008). Chem. Soc. Rev. 37, 308-319.  [ISI] [CrossRef] [PubMed] [ChemPort]
Reichenbacher, K., Suss, H. I. & Hulliger, J. (2005). J. Chem. Soc. Rev. 34, 22-30.  [CrossRef]
Thalladi, V. R., Weiss, H. C., Bläser, D., Boese, R., Nangia, A. & Desiraju, G. R. (1998). J. Am. Chem. Soc. 120, 8702-8710.  [ISI] [CrossRef] [ChemPort]
The GIMP team (2008). The GNU Image Manipulation Program, http://www.gimp.org.
Weiss, H. C., Boese, R., Smith, H. L. & Haley, M. M. (1997). Chem. Commun. pp. 2403-2404.  [CrossRef]
Westrip, S. P. (2009). publCIF. In preparation.


Acta Cryst (2009). E65, o2670  [ doi:10.1107/S1600536809038975 ]

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