Biphenyl-3,3′-dicarb­oxy­lic acid

Deng, S.-H.; Zhao, J.; Mu, Y.-Q.; Li, C.; Liu, H.-M.

doi:10.1107/S1600536811014334

Volume 67
Part 5
Page o1221
May 2011

Received 9 April 2011
Accepted 16 April 2011
Online 29 April 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.052
wR = 0.155
Data-to-parameter ratio = 15.5
Details

Biphenyl-3,3'-dicarboxylic acid

Shao-Hua Deng,^a Jun Zhao,^a ^* Yi-Qiang Mu,^a Cai Li ^a and Hui-Min Liu ^a

^aCollege of Mechanical and Materials Engineering, China Three Gorges University, Yichang, Hubei 443002, People's Republic of China
Correspondence e-mail: junzhao08@126.com

The asymmetric unit of the title compound, C₁₄H₁₀O₄, contains one half molecule, the complete molecule being generated by a twofold axis. The two benzene rings form a dihedral angle of 43.11 (5)°. Intermolecular O-HO hydrogen bonds link the molecules into one-dimensional zigzag chains. These chains are further connected into two-dimensional supramolecular layers by weak [pi] - [pi] stacking interactions between neighbouring benzene rings, with centroid-centroid distances of 3.7648 (8) Å.

Related literature

For general background non-covalent intermolecular interactions, see: Etter et al. (1990); Desiraju (2003); Yaghi et al. (2003); Li et al. (2010). For the structures of related complexes, see: Wang et al. (2005); Zhu (2010).

Experimental

Crystal data

C₁₄H₁₀O₄
M_r = 242.22
Monoclinic, P 2/n
a = 6.6123 (9) Å
b = 3.7648 (8) Å
c = 22.554 (3) Å
= 93.14 (2)°
V = 560.61 (15) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 296 K
0.21 × 0.18 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.978, T_max = 0.986
5212 measured reflections
1286 independent reflections
1006 reflections with I > 2(I)
R_int = 0.107

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.155
S = 1.04
1286 reflections
83 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.82	1.82	2.6268 (17)	169
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2097 ).

Acknowledgements

The authors are grateful to the Natural Science Foundation of Hubei Province of China (grant No. 2010CDB10707) and the Project of Hubei Provincial Education Office (grant No. Q20101203).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. (2003). J. Mol. Struct. 656, 5-15.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Li, D. S., Wu, Y. P., Zhang, P., Du, M., Zhao, J., Li, C. P. & Wang, Y. Y. (2010). Cryst. Growth Des. 10, 2037-2040.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, R. H., Han, L., Jiang, F. L., Zhou, Y. F., Yuan, D. Q. & Hong, M. C. (2005). Cryst. Growth Des. 5, 129-135.
Yaghi, O. M., O'Keeffe, M., Ockwing, N. W., Chae, H. K., Eddaoudi, M. & Kim, J. (2003). Nature (London), 423, 705-714.
Zhu, B.-Y. (2010). Acta Cryst. E66, m1214.

organic compounds