4,4′-[4,4′-Sulfonyl­bis­(p-phenyl­ene­oxy)]dibutanoic acid

Fu, C.-Y.; Liu, Y.-H.; Zhou, Z.-L.; Tang, H.

doi:10.1107/S1600536811011871

Volume 67
Part 5
Page o1048
May 2011

Received 16 March 2011
Accepted 30 March 2011
Online 7 April 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.045
wR = 0.139
Data-to-parameter ratio = 13.3
Details

4,4'-[4,4'-Sulfonylbis(p-phenyleneoxy)]dibutanoic acid

Chun-Yan Fu,^a ^* Yong-Hui Liu,^b Zhong-Liu Zhou ^c and Hong Tang ^a

^aShaoyang Medical College Level Specialty School, Department of Pharmacy, Shaoyang, Hunan 422000, People's Republic of China,^bRed Cross Hospital at Xinshao County of Hunan Province, Shaoyang, Hunan 422000, People's Republic of China, and ^cChemistry Science and Technology School, Zhanjiang Normal University, Zhanjiang, Guangdong 524048, People's Republic of China
Correspondence e-mail: chunyanfu@tom.com

In the title compound, C₂₀H₂₂O₈S, the dihedral angle between the two benzene rings is 81.6 (3)°. The benzene-connected portions of the alkoxy substituents are almost coplanar with their respective rings [C-C-O-C torsion angles of 174.77 (17) and -178.5 (4)°]. One of the butanoic acid groups is disordered over two conformations with a site-occupancy ratio 0.719 (6):0.281 (6). In the crystal, pairs of O-HO hydrogen bonds link the molecules into infinite zigzag chains along [130].

Related literature

For bisphenol S (systematic name 4,4'-sulfonyldiphenol) as a reactant in epoxy reactions and its use in fast-curing epoxy resin glues, see: Askarinejad & Morsali (2006); Danzl et al. (2009); Bashiri et al. (2009). For its use in the manufacture of pharmaceuticals, adhesives, biocides and agricultural products, see: Howard & David (2002); Howard et al. (2005); Yasue et al. (2009). For synthesis details and a related structure, see: Zheng et al. (2007).

Experimental

Crystal data

C₂₀H₂₂O₈S
M_r = 422.45
Monoclinic, C 2/c
a = 30.945 (7) Å
b = 8.0964 (18) Å
c = 16.032 (3) Å
= 94.711 (5)°
V = 4003.1 (15) Å³
Z = 8
Mo K radiation
= 0.21 mm^-1
T = 296 K
0.20 × 0.18 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.959, T_max = 0.975
12299 measured reflections
4362 independent reflections
2927 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.139
S = 1.00
4362 reflections
327 parameters
19 restraints
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O8B-H8BO2ⁱ	0.82	2.07	2.890 (11)	180
O8-H8AO2ⁱ	0.82	1.77	2.587 (4)	178
O3-H3O7Bⁱⁱ	0.82	1.84	2.623 (13)	159
O3-H3O7ⁱⁱ	0.82	1.85	2.668 (5)	177
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{3\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, y-{\script{3\over 2}}, z]$ .

Data collection: SMART (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: PK2315 ).

Acknowledgements

The authors gratefully acknowledge financial support from the Education Department of Hunan Province (grant No. 10C0294).

References

Askarinejad, A. & Morsali, A. (2006). Inorg. Chem. Commun., 9, 143-146.
Bashiri, R., Akhbari, K. & Morsali, A. (2009). Inorg. Chim.Acta, 362, 1035-1041.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Danzl, E., Sei, K., Soda, S., Ike, M. & Fujita, M. (2009). Int. J. Environ. Res. Public Health, 6, 1472-1484.
Howard, M. C. & David, F. L. (2002). Macromolecules, 35, 6875-6882.
Howard, M. C., Zhu, Z. X., Christopher, C. D., Caroline, A. O., David, J. W. & Michael, G. B. D. (2005). Macromolecules, 38, 10413-10420.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yasue, S., Maeda, K. & Uchida, F. (2009). Inorg. Chem. Commun. 12, 336-339.
Zheng, Z.-B., Wu, R.-T., Ji, N.-N. & Sun, Y.-F. (2007). Acta Cryst. E63, o3936.

organic compounds