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Volume 69 
Part 8 
Page o1206  
August 2013  

Received 25 June 2013
Accepted 2 July 2013
Online 6 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.098
Data-to-parameter ratio = 14.1
Details
Open access

Bifenox: methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate

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

In the title compound, the herbicide bifenox, C14H9Cl2NO5, the dihedral angle between the dichlorobenzene and nitrobenzene rings is 78.79 (14)°. In the crystal, C-H...O hydrogen bonds give rise to a three-dimensional network structure in which there are both a [pi]-[pi] interaction [ring centroid separation = 3.6212 (16) Å] and a C-Cl...[pi] interaction [Cl...ring centroid = 3.4754 (8) Å]. In addition, short Cl...Cl contacts [3.3767 (11) and 3.3946 (11) Å] are present.

Related literature

For information on the insecticidal activity of the title compound, see: Jinno et al. (1999[Jinno, H., Hatakeyama, N., Hanioka, N., Yoda, R., Nishimura, T. & Ando, M. (1999). Food Chem. Toxicol. 37, 69-74.]); O'Neil (2001[O'Neil, M. J. (2001). The Merck Index, 13th ed., p. 206. Whitehouse Station, NJ, USA: Merck & Co. Inc.]). For a related crystal structure, see: Smith et al. (1981[Smith, G., Kennard, C. H. L., White, A. H. & Skelton, B. W. (1981). J. Agric. Food Chem. 29, 1046-1049.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9Cl2NO5

  • Mr = 342.12

  • Triclinic, [P \overline 1]

  • a = 8.4945 (7) Å

  • b = 9.9610 (8) Å

  • c = 10.3969 (8) Å

  • [alpha] = 64.601 (1)°

  • [beta] = 68.720 (1)°

  • [gamma] = 70.421 (1)°

  • V = 723.48 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.47 mm-1

  • T = 173 K

  • 0.20 × 0.10 × 0.10 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 = 0.912, Tmax = 0.954

  • 5707 measured reflections

  • 2830 independent reflections

  • 2217 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.098

  • S = 1.06

  • 2830 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O4i 0.95 2.41 3.290 (3) 153
C6-H6...O5ii 0.95 2.43 3.243 (3) 143
C8-H8...O2iii 0.95 2.58 3.435 (3) 151
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z+1; (iii) x+1, y, z.

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.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2269 ).


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

Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Jinno, H., Hatakeyama, N., Hanioka, N., Yoda, R., Nishimura, T. & Ando, M. (1999). Food Chem. Toxicol. 37, 69-74.  [Web of Science] [PubMed] [ChemPort]
O'Neil, M. J. (2001). The Merck Index, 13th ed., p. 206. Whitehouse Station, NJ, USA: Merck & Co. Inc.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smith, G., Kennard, C. H. L., White, A. H. & Skelton, B. W. (1981). J. Agric. Food Chem. 29, 1046-1049.  [CrossRef] [ChemPort] [Web of Science]


Acta Cryst (2013). E69, o1206  [ doi:10.1107/S1600536813018266 ]

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