Received 28 July 2009
In the title compound, C14H12N2O6, the half molecule in the asymmetric unit of the cell is completed by a crystallographic twofold rotation axis, and the two benzene rings of the complete molecule make a dihedral angle of 60.5 (3)°. Furthermore, intermolecular weak C-HO hydrogen bonds link adjacent molecules, forming a two-dimensional sheet. These sheets are stablized by face-to-face weak - contacts [centroid-centroid distance = 3.682 (1) Å] between the nearly parallel [dihedral angle = 0.12 (7)°] benzene rings of the neighboring molecules, resulting in a three-dimensional network.
For the synthesis of the title compound, see: Chen et al. (2001). For asymmetric synthesis using chiral ligands with C2 symmetry, see: Jiang et al. (2001); García et al. (2002). For synthetic methods for chiral compounds, see: Brunel (2005); Kocovský et al. (2003). For related biphenyl structures, see: Fischer et al. (2007). For related structural data see: Yang et al. (2005).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 and PLATON.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2193 ).
This work was supported by the Youth Foundation of Luoyang Normal University (No. 10000409).
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Brunel, J. M. (2005). Chem. Rev. 105, 857-897.
Chen, Y. X., Li, Y. M., Lam, k. H., & Chan, A. S. C. (2001). Chin. J. Chem. 19, 794-799.
Fischer, A., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2007). Acta Cryst. E63, o1357-o1358.
García, C., LaRochelle, L. K. & Walsh, P. J. (2002). J. Am. Chem. Soc. 124, 10970-10971.
Jiang, B., Feng, Y. & Hang, J. F. (2001). Tetrahedron Asymmetry. 12, 2323-2329.
Kocovský, P., Vyskocil, S. & Smrcina, M. (2003). Chem. Rev. 103, 3213-3245.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yang, D. S., Ma, H. X., Hu, R. Z., Song, J. R. & Zhao, F. Q. (2005). J. Mol. Struct. 779, 49-54.