Received 27 May 2013
The title compound, C12H10N2O2, has a twisted conformation, with a dihedral angle between the planes of the pyridine and benzene rings of 78.4 (2)°. The nitro group is coplanar with the attached benzene ring within experimental error. The molecules form centrosymmetric dimers via Car-HO interactions (HO = 2.49 Å) and the dimers are -stacked along the b axis [the separation between ring centroids is 3.788 (2) Å].
For adducts of the title compound with different organic acids, see: Smith et al. (1997); Smith & Wermuth (2010, 2013). For a zinc complex of the title compound, see: Smith et al. (2011). For the analysis of -stacking interactions, see: Dolomanov et al. (2009).
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2106 ).
The authors thank the University of Jordan and Hamdi Mango Center for Scientific Research for providing support and time to collect the single-crystal X-ray diffraction data set.
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1997). J. Chem. Crystallogr. 27, 307-317.
Smith, G. & Wermuth, U. D. (2010). Acta Cryst. E66, o1173.
Smith, G. & Wermuth, U. D. (2013). Acta Cryst. E69, o206.
Smith, G., Wermuth, U. D. & Williams, M. L. (2011). Acta Cryst. E67, m359.