2,2′-Dimeth­oxy-6,6′-dinitro­biphen­yl

Miao, S.-B.; Deng, D.-S.; Liu, X.-M.; Ji, B.-M.

doi:10.1107/S1600536809033790

Volume 65
Part 10
Page o2314
October 2009

Received 28 July 2009
Accepted 24 August 2009
Online 5 September 2009

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.097
Data-to-parameter ratio = 12.9
Details

2,2'-Dimethoxy-6,6'-dinitrobiphenyl

Shao-Bin Miao,^a Dong-Sheng Deng,^a Xian-Ming Liu ^a and Bao-Ming Ji ^a ^*

^aCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China
Correspondence e-mail: lyhxxjbm@126.com

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 [pi] - [pi] 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.

Related literature

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).

Experimental

Crystal data

C₁₄H₁₂N₂O₆
M_r = 304.26
Monoclinic, C 2/c
a = 18.236 (3) Å
b = 7.7826 (12) Å
c = 10.9079 (17) Å
= 115.089 (2)°
V = 1402.0 (4) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 294 K
0.30 × 0.18 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.966, T_max = 0.979
5102 measured reflections
1298 independent reflections
1009 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.097
S = 1.03
1298 reflections
101 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7BO3ⁱ	0.96	2.48	3.426 (3)	169
Symmetry code: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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 ).

Acknowledgements

This work was supported by the Youth Foundation of Luoyang Normal University (No. 10000409).

References

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.

organic compounds