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Volume 70 
Part 1 
Page o100  
January 2014  

Received 11 November 2013
Accepted 19 December 2013
Online 24 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.062
wR = 0.140
Data-to-parameter ratio = 14.4
Details
Open access

2-(2-Fluoro-4-nitro­phen­oxy)-3-nitro­pyridine

aDepartment of Chemistry and Chemical Engineering, Changchun University of Science and Technology, Changchun 130022, People's Republic of China
Correspondence e-mail: cuilili1127@gmail.com

In the title compound, C11H6FN3O5, the dihedral angle between the aromatic rings is 72.4 (3)°. The NO2 groups form dihedral angles of 40.8 (2) and 4.8 (2)°, respectively, with the attached pyridine and benzene rings. The crystal structure features [pi]-[pi] stacking between centrosymmetrically related pairs of pyridine rings [centroid-centroid separation = 3.800 (3) Å].

Related literature

For applications and the biological activity of 2-phen­oxy­pyridine, see: Chao et al. (2013[Chao, H., Turdi, H., Herpin, T. F., Roberge, J. Y., Liu, Y., Schnur, D. M., Poss, M. A., Rehfuss, R., Hua, J., Wu, Q., Price, L. A., Abell, L. M., Schumacher, W. A., Bostwick, J. S., Steinbacher, T. E., Stewart, A. B., Ogletree, M. L., Huang, C. S., Chang, M., Cacace, A. M., Arcuri, M. J., Celani, D., Wexler, R. R. & Lawrence, R. M. (2013). J. Med. Chem. 56, 1704-1714.]).

[Scheme 1]

Experimental

Crystal data
  • C11H6FN3O5

  • Mr = 279.19

  • Monoclinic, P 21 /c

  • a = 7.5275 (15) Å

  • b = 21.804 (4) Å

  • c = 7.1681 (14) Å

  • [beta] = 101.07 (3)°

  • V = 1154.6 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 293 K

  • 0.41 × 0.36 × 0.22 mm

Data collection
  • Rigaku R-AXIS RAPID IP diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.945, Tmax = 0.970

  • 10606 measured reflections

  • 2611 independent reflections

  • 1351 reflections with I > 2[sigma](I)

  • Rint = 0.083

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.140

  • S = 0.94

  • 2611 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: PK2504 ).


Acknowledgements

The project was sponsored by the Natural Science Foundation of China (No. 21273024) and the Natural Science Foundation of Jilin Province, China (No. 201215135).

References

Chao, H., Turdi, H., Herpin, T. F., Roberge, J. Y., Liu, Y., Schnur, D. M., Poss, M. A., Rehfuss, R., Hua, J., Wu, Q., Price, L. A., Abell, L. M., Schumacher, W. A., Bostwick, J. S., Steinbacher, T. E., Stewart, A. B., Ogletree, M. L., Huang, C. S., Chang, M., Cacace, A. M., Arcuri, M. J., Celani, D., Wexler, R. R. & Lawrence, R. M. (2013). J. Med. Chem. 56, 1704-1714.  [CrossRef] [ChemPort] [PubMed]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o100  [ doi:10.1107/S1600536813034181 ]

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