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Volume 67 
Part 4 
Page o957  
April 2011  

Received 14 March 2011
Accepted 17 March 2011
Online 23 March 2011

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.147
Data-to-parameter ratio = 19.2
Details
Open access

8-Nitroquinoline

Liang Xu,a Bao-Li Xu,a Shu-Jun Lu,a Bing Wanga and Ting-Guo Kanga*

aLiaoning University of Traditional Chinese Medicine, Dalian 116600, People's Republic of China
Correspondence e-mail: lnzyxuliang@eyou.com

The molecule of the title compound, C9H6N2O2, is almost planar, with a dihedral angle of 3.0 (9)° between the pyridine and benzene rings.

Related literature

For the first synthesis of 8-nitroquinoline, see: Königs (1879[Königs, W. (1879). Chem. Ber. 12, 448-451.]). The crystal studied was synthesised according to the method of Yale & Bernstein (1948[Yale, H. L. & Bernstein, J. (1948). J. Am. Chem. Soc. 70, 254-254.]). For the pharmacological activity of quinoline derivatives, see: Franck et al. (2004[Franck, X., Fournet, A., Prina, E., Mahieux, R., Hocquemiller, R. & Figadere, B. (2004). Bioorg. Med. Chem. Lett. 14, 3635-3638.]); Zouhiri et al. (2005[Zouhiri, F., Danet, M., Benard, C., Normand-Bayle, M., Mouscadet, J. F., Leh, H., Thomas, C. M., Mbemba, G., D'Angelo, J. & Desmaele, D. (2005). Tetrahedron Lett. 46, 2201-2205.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin. Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C9H6N2O2

  • Mr = 174.16

  • Monoclinic, P 21 /c

  • a = 7.2421 (11) Å

  • b = 16.688 (3) Å

  • c = 7.2089 (11) Å

  • [beta] = 114.086 (4)°

  • V = 795.4 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.40 × 0.32 × 0.25 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • 10084 measured reflections

  • 2287 independent reflections

  • 1827 reflections with I > 2[sigma](I)

  • Rint = 0.023
Refinement

  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.147

  • S = 1.03

  • 2287 reflections

  • 119 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2003[Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5010 ).

Acknowledgements

The authors thank Liaoning University of Traditional Chinese Medicine for supporting this study (No. YXRC0920).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin. Trans. 2, pp. S1-19.
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Franck, X., Fournet, A., Prina, E., Mahieux, R., Hocquemiller, R. & Figadere, B. (2004). Bioorg. Med. Chem. Lett. 14, 3635-3638.  [CrossRef] [PubMed] [ChemPort]
Königs, W. (1879). Chem. Ber. 12, 448-451.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yale, H. L. & Bernstein, J. (1948). J. Am. Chem. Soc. 70, 254-254.  [PubMed] [ChemPort]
Zouhiri, F., Danet, M., Benard, C., Normand-Bayle, M., Mouscadet, J. F., Leh, H., Thomas, C. M., Mbemba, G., D'Angelo, J. & Desmaele, D. (2005). Tetrahedron Lett. 46, 2201-2205.  [ISI] [CrossRef] [ChemPort]

Acta Cryst (2011). E67, o957  [ doi:10.1107/S1600536811010014 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.