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Volume 64 
Part 2 
Page o430  
February 2008  

Received 29 October 2007
Accepted 17 November 2007
Online 11 January 2008

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© International Union of Crystallography 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.049
wR = 0.137
Data-to-parameter ratio = 9.4
Details
Open access

3-Chloro-5-(trifluoromethyl)pyridin-2-amine

Sheng Tan,a* Guang-Bin Feng,a Xue-Jun Chena and Zhen-Hua Shangb

aOrdnance Technology Institute, Ordnance Engineering College, Shijiazhuang 050003, People's Republic of China, and bCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China
Correspondence e-mail: shengtan2007@yahoo.com.cn

In the title compound, C6H4ClF3N2, an intermediate in the synthesis of the fungicide fluazinam, the F atoms of the trifluoromethyl group are disordered over two sites in a 0.683 (14):0.317 (14) ratio. In the crystal structure, centrosymmetric dimers arise from pairs of N-H...N hydrogen bonds.

Related literature

For related literature, see: Guo et al. (1991[Guo, Z.-J., Miyoshi, H., Komyoji, T., Haga, T. & Fujita, T. (1991). Biochim. Biophys. Acta, 1056, 89-92.]).

[Scheme 1]

Experimental

Crystal data

  • C6H4ClF3N2

  • Mr = 196.56

  • Monoclinic, P 21 /n

  • a = 5.801 (1) Å

  • b = 17.978 (5) Å

  • c = 7.578 (2) Å

  • [beta] = 100.19 (4)°

  • V = 777.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.49 mm-1

  • T = 294 (2) K

  • 0.24 × 0.22 × 0.20 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SADABS (Version 2.0), SMART (Version 5.611), SAINT (Version 6.0) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.893, Tmax = 0.909

  • 3820 measured reflections

  • 1368 independent reflections

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

  • Rint = 0.054
Refinement

  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.137

  • S = 1.01

  • 1368 reflections

  • 145 parameters

  • 39 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 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
N2-H2A...Cl1 0.89 (2) 2.60 (3) 2.965 (9) 105.3 (19)
N2-H2B...N1i 0.89 (3) 2.16 (3) 3.049 (9) 171 (3)
Symmetry code: (i) -x-1, -y+1, -z.

Data collection: SMART (Bruker, 1997[Bruker (1997). SADABS (Version 2.0), SMART (Version 5.611), SAINT (Version 6.0) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SADABS (Version 2.0), SMART (Version 5.611), SAINT (Version 6.0) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 1997[Bruker (1997). SADABS (Version 2.0), SMART (Version 5.611), SAINT (Version 6.0) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2620 ).

Acknowledgements

The authors thank the fund of the Ordnance Technology Institute for support.

References

Bruker (1997). SADABS (Version 2.0), SMART (Version 5.611), SAINT (Version 6.0) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.
Guo, Z.-J., Miyoshi, H., Komyoji, T., Haga, T. & Fujita, T. (1991). Biochim. Biophys. Acta, 1056, 89-92.  [ChemPort]
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Acta Cryst (2008). E64, o430  [ doi:10.1107/S1600536807060205 ]