1,2,3-Trifluoro­benzene

Kirchner, M.T.; Bläser, D.; Boese, R.; Thakur, T.S.; Desiraju, G.R.

doi:10.1107/S1600536809038975

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 (C-C) = 0.004 Å
R = 0.061
wR = 0.226
Data-to-parameter ratio = 14.4
Details

1,2,3-Trifluorobenzene

Michael T. Kirchner,^a Dieter Bläser,^a Roland Boese,^a ^* Tejender S. Thakur ^b and Gautam R. Desiraju ^b ^*

^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-HF hydrogen bonds. These tapes are, in turn, connected into corrugated two-dimensional sheets by bifurcated C-HF 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-HF interactions, see: Althoff et al. (2006); Bats et al. (2000); Choudhury et al. (2004); D'Oria & Novoa (2008); Dunitz & Taylor (1997); Howard et al. (1996); Müller et al. (2007); O'Hagan (2008); Reichenbacher et al. (2005); Weiss et al. (1997). For related crystal structures of several polyfluorinated benzenes, see: Thalladi et al. (1998). For crystallization techniques, see: Boese & Nussbaumer (1994).

Experimental

Crystal data

C₆H₃F₃
M_r = 132.08
Monoclinic, C 2/c
a = 7.4238 (19) Å
b = 11.590 (3) Å
c = 7.0473 (17) Å
= 112.783 (4)°
V = 559.1 (2) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.820, T_max = 0.953
1074 measured reflections
634 independent reflections
413 reflections with I > 2(I)
R_int = 0.013

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.226
S = 1.04
634 reflections
44 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3F2ⁱ	1.10	2.77	3.560 (3)	129
C3-H3F1ⁱⁱ	1.10	2.59	3.528 (4)	144
C4-H4F2ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2008); 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) and GIMP2 (The GIMP team, 2008); software used to prepare material for publication: publCIF (Westrip, 2009).

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

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organic compounds