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Volume 69 
Part 9 
Page o1467  
September 2013  

Received 27 July 2013
Accepted 19 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.085
Data-to-parameter ratio = 15.6
Details
Open access

Fluazinam

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr

In the asymmetric unit of the title compound {systematic name: 3-chloro-N-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2,6-dinitro-4-(trifluoromethyl)aniline}, C13H4Cl2F6N4O4, which is the fungicide fluazinam, the dihedral angle between the pyridine and benzene ring planes is 42.20 (4)°. In the crystal, pairs of N-H...F hydrogen bonds link the molecules into inversion dimers which are linked by C-Cl...[pi] [Cl...ring centroid = 3.3618 (4) A °] and N-O...[pi] [O...ring centroid = 3.1885 (16) Å] interactions into chains along [100]. In addition, short Cl...Cl, O...Cl, and F...F contacts [3.4676 (7), 3.2371 (13) and 2.7910 (15) Å] are present which connect the chains, yielding a three-dimensional network.

Related literature

For information on the toxicity and fungicidal properties of the title compound, see: Yoshida & Yukimoto (1993[Yoshida, M. & Yukimoto, M. (1993). Pestic. Biochem. Physiol. 47, 171-177.]); Draper et al. (2003[Draper, A., Cullinan, P., Campbell, C., Jones, M. & Taylor, A. N. (2003). Occup. Environ. Med. 60, 76-77.]). For a related structure, see: McCullough et al. (1972[McCullough, J. D., Paul, I. C. & Curtin, D. Y. (1972). J. Am. Chem. Soc. 94, 883-889.]).

[Scheme 1]

Experimental

Crystal data
  • C13H4Cl2F6N4O4

  • Mr = 465.10

  • Triclinic, [P \overline 1]

  • a = 8.9546 (1) Å

  • b = 9.0724 (1) Å

  • c = 10.6818 (2) Å

  • [alpha] = 79.556 (1)°

  • [beta] = 75.420 (1)°

  • [gamma] = 83.451 (1)°

  • V = 823.79 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.49 mm-1

  • T = 173 K

  • 0.30 × 0.18 × 0.15 mm

Data collection
  • Bruker APEXII CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.867, Tmax = 0.930

  • 15193 measured reflections

  • 4096 independent reflections

  • 3662 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.085

  • S = 1.04

  • 4096 reflections

  • 262 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...F3i 0.88 2.52 3.0690 (15) 121
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. 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.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2230 ).


Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2012R1A1B3003337).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Draper, A., Cullinan, P., Campbell, C., Jones, M. & Taylor, A. N. (2003). Occup. Environ. Med. 60, 76-77.  [ISI] [CrossRef] [PubMed] [ChemPort]
McCullough, J. D., Paul, I. C. & Curtin, D. Y. (1972). J. Am. Chem. Soc. 94, 883-889.  [CSD] [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Yoshida, M. & Yukimoto, M. (1993). Pestic. Biochem. Physiol. 47, 171-177.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2013). E69, o1467  [ doi:10.1107/S1600536813023210 ]

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