3,3′-[Biphenyl-4,4′-diylbis(­oxy)]diphthalic acid

Zhao, N.; Li, W.; Chang, Z.; Sun, C.; Fan, H.

doi:10.1107/S1600536811053219

Volume 68
Part 1
Page o211
January 2012

Received 21 November 2011
Accepted 10 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.048
wR = 0.118
Data-to-parameter ratio = 8.3
Details

3,3'-[Biphenyl-4,4'-diylbis(oxy)]diphthalic acid

Ningning Zhao,^a Wenjun Li,^a ^* Zhidong Chang,^a Changyan Sun ^a and Hongxia Fan ^a

^aDepartment of Chemistry and Chemical Engineering, University of Science and Technology Beijing, Beijing 100083, People's Republic of China
Correspondence e-mail: wjli@sas.ustb.edu.cn

In the title molecule, C₂₈H₁₈O₁₀, the two central benzene rings form a dihedral angle of 31.0 (1)°. In the phthalic acid fragments, the carboxy groups in the meta positions are approximately coplanar with the attached benzene rings, being inclined to their planes at 2.7 (1) and 10.3 (1)°, while the carboxy groups in the ortho positions are twisted from the benzene ring planes by 83.5 (1) and 75.4 (1)°. In the crystal, O-HO hydrogen bonds link the molecules into layers parallel to the bc plane. Weak C-HO hydrogen bonds and [pi] - [pi] interactions between the aromatic rings [centroid-centroid distance = 3.7674 (3) Å] further consolidate the crystal packing.

Related literature

For applications of metal-organic frameworks with semi-rigid carboxylic acid ligands, see: Li et al. (2008); Chen et al. (2008). For background to the synthesis of various semi-rigid multicarboxylate ligands, see: Maglio et al. (1997).

Experimental

Crystal data

C₂₈H₁₈O₁₀
M_r = 514.42
Orthorhombic, P n a 2₁
a = 21.5817 (7) Å
b = 11.2676 (4) Å
c = 9.5025 (3) Å
V = 2310.76 (13) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 293 K
0.39 × 0.32 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.957, T_max = 0.969
5587 measured reflections
2857 independent reflections
2352 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.118
S = 1.08
2857 reflections
343 parameters
1 restraint
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O7ⁱ	0.82	1.85	2.649 (4)	164
O8-H8AO1ⁱⁱ	0.82	1.85	2.659 (4)	169
O3-H3O6ⁱⁱⁱ	0.82	1.76	2.575 (4)	172
O5-H5O4^iv	0.82	1.92	2.732 (4)	169
C11-H11O6^v	0.93	2.46	3.284 (5)	148
C13-H13O3^vi	0.93	2.51	3.438 (6)	173
C16-H16O6^v	0.93	2.54	3.431 (6)	161
Symmetry codes: (i) x, y+1, z+2; (ii) x, y-1, z-2; (iii) $[-x+1, -y+2, z+{\script{3\over 2}}]$ ; (iv) $[-x+1, -y+2, z-{\script{3\over 2}}]$ ; (v) x, y, z+1; (vi) x, y, z-1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: CV5208 ).

Acknowledgements

This project was supported by the National Natural Science Foundation of China (grant No. 21101013) and the Foundation of University of Science and Technology Beijing (grant Nos. 00009805 and 06113004).

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, X.-L., Zhang, B., Hu, H.-M., Fu, F., Wu, X.-L., Qin, T., Yang, M.-L., Xue, G.-L. & Wang, J.-W. (2008). Cryst. Growth Des. 8, 3706-3712.
Li, S.-L., Lan, Y.-Q., Ma, J.-F., Yang, J., Wei, G.-H., Zhang, L.-P. & Su, Z.-M. (2008). Cryst. Growth Des. 8, 1610-1616.
Maglio, G., Palumbo, R., Schioppa, A. & Tesauro, D. (1997). Polymer, 38, 5849-5856.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds