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

Chun-Yan Fu; Yong-Hui Liu; Zhong-Liu Zhou; Hong Tang

doi:10.1107/S1600536811011871

. 2011 Apr 7;67(Pt 5):o1048. doi: 10.1107/S1600536811011871

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

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

PMCID: PMC3089177 PMID: 21754375

Abstract

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—H⋯O 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,
a = 30.945 (7) Å
b = 8.0964 (18) Å
c = 16.032 (3) Å
β = 94.711 (5)°
V = 4003.1 (15) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.139
S = 1.00
4362 reflections
327 parameters
19 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011871/pk2315sup1.cif

e-67-o1048-sup1.cif^{(24.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011871/pk2315Isup2.hkl

e-67-o1048-Isup2.hkl^{(213.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8B—H8B⋯O2ⁱ	0.82	2.07	2.890 (11)	180
O8—H8A⋯O2ⁱ	0.82	1.77	2.587 (4)	178
O3—H3⋯O7Bⁱⁱ	0.82	1.84	2.623 (13)	159
O3—H3⋯O7ⁱⁱ	0.82	1.85	2.668 (5)	177

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

Bisphenol S (BPS) is an organic compound with the formula (C₆H₄OH)₂SO₂. It has two phenol functional groups on either side of a sulfonyl group. It is commonly used as a reactant in epoxy reactions, and is used in fast-curing epoxy resin glues (Askarinejad & Morsali, 2006; Bashiri et al., 2009; Danzl et al., 2009; Yasue et al., 2009). Bisphenol S is also used in organic synthesis as an organosulfur source in the manufacture of pharmaceuticals, adhesives, biocides and agricultural products (Howard & David, 2002; Howard et al., 2005). In this article, we present the synthesis and crystal structure of a new potential ligand derived from bisphenol S, which contains multiple oxygen donors and flexible aliphatic spacers.

As shown in Figure 1, the benzene-connected portions of the alkoxy substituents lie almost coplanar with the ring [C–C–O–C torsion angle = 174.77 (17) and -178.5 (4)°, respectively]. The two benzene rings make a dihedral angle of 81.6 (3)°. It is noteworthy that one of the butanoic acid groups is disordered over two components with site occupancy ratio 0.719 (6):0.281 (6). In the crystal, O—H···O hydrogen bonds link the molecules into a zigzag 1-D infinite chain that propagates along the [1 3 0] direction. These chains are further interwoven by C—H···O and C—H···π contacts that stabilize the packing.

Experimental

Reagents and solvents were of commercially available quality. The title complex was synthesized according to the method of Zheng et al., 2007. To a solution of bisphenol S (0.01 mol) in acetonitrile (50 ml), anhydrous potassium carbonate (0.02 mol) and ethyl 4-bromobutanoate (0.01 mol) were mixed. The mixture solution was refluxed for 6 h and filtered. The filtrate was evaporated under reduced pressure and the solid product was dissolved in water/ethanol (1:2 v/v), then sodium hydroxide (0.02 mol) was added. The solution was refluxed for another 24 h, then acidified with dilute HCl. The crude product was separated by filtration and crystals of the title compound were prepared by recrystallization from a mixture of water and ethanol (1:1).