Bis(4-pyrid­yl) disulfide–2,2′-[(p-phenyl­enebis(­oxy)]diacetic acid (1/1)

Guang-Yin Wang

doi:10.1107/S1600536811025694

. 2011 Jul 6;67(Pt 8):o1923. doi: 10.1107/S1600536811025694

Bis(4-pyridyl) disulfide–2,2′-[(p-phenylenebis(oxy)]diacetic acid (1/1)

Guang-Yin Wang ^a,^*

PMCID: PMC3212313 PMID: 22090970

Abstract

The asymmetric unit of the title 1:1 co-crystal, C₁₀H₈N₂S₂·C₁₀H₁₀O₆, comprises two half-molecules, the bis(4-pyridyl) disulfide having twofold rotational symmetry and the 2,2′-[(p-phenylenebis(oxy)]diacetic acid having crystallographic inversion symmetry. In the disulfide molecule, the dihedral angle between the two pyridine rings is 86.8 (1)°, while the carboxyl groups of the substituted quinone lie essentially in the plane of the benzene ring [dihedral angle = 5.3 (1)°]. In the crystal, the components are linked via intermolecular O—H⋯N hydrogen bonds into zigzag chains which extend along c and are interlinked through C—H⋯π associations.

Related literature

For the use of bis(4-pyridyl)disulfide (bpds) as a linker in the construction of coordination polymers, see: Kondo et al. (2000 ▶); Zhu et al. (2010 ▶).

Experimental

Crystal data

C₁₀H₈N₂S₂·C₁₀H₁₀O₆
M _r = 446.50
Monoclinic,
a = 14.331 (1) Å
b = 5.057 (1) Å
c = 28.003 (3) Å
β = 90.200 (5)°
V = 2029.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.31 × 0.21 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.912, T _max = 0.974
4893 measured reflections
1761 independent reflections
1450 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.114
S = 1.05
1761 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025694/zs2125sup1.cif

e-67-o1923-sup1.cif^{(15KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025694/zs2125Isup2.hkl

e-67-o1923-Isup2.hkl^{(86.9KB, hkl)}

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

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

Cg1 is the centroid of the C8–C10/C8′–C10′ ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1ⁱ	0.82	1.81	2.629 (3)	174
C7—H7B⋯Cg1ⁱⁱ	0.97	2.76	3.528 (2)	136

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

Acknowledgments

This work was supported financially by the Project of Shandong Province Higher Educational Science and Technology Program (grant No. J11LB56).

supplementary crystallographic information

Comment

Bis(4-pyridyl)disulfide (bpds) is often used as a linker in the construction of coordination polymers because of its flexibility (Kondo et al., 2000; Zhu et al., 2010). The attempt at synthesizing a Cd^II coordination polymer using bis(4-pyridyl)disulfide and hydroquinone-O,O'-diacetic acid (H₂qda) as ligands gave instead the 1:1 title co-crystal C₁₀H₈N₂S₂ . C₁₀H₁₀O₆, and the crystal structure is reported here.

In the title compound, the asymmetric unit comprises two half molecules, the bis(4-pyridyl)disulfide having twofold rotational symmetry and the hydroquinone-O,O'-diacetic acid having crystallographic inversion symmetry (Fig. 1). In the disulfide molecule, the dihedral angle between the two pyridine rings is 93.2 (1)° while the carboxylic acid groups of the substituted quinone molecule lie essentially in the plane of the benzene ring [dihedral angle, 5.3 (1)°]. In the crystal, the two components are linked via intermolecular O—H···N hydrogen bonds into one-dimensional zigzag chains which extend along c (Fig. 2) and are inter-linked through C—H···π associations (Table 1, Fig. 3).

Experimental

A mixture of hydroquinone-O,O'-diacetic acid (H₂qda) (0.023 g, 0.1 mmol), bis(4-pyridyl)disulfide (bpds) (0.022 g, 0.1 mmol) and Cd(NO₃)₂ . 4H₂O (0.038 g, 0.1 mmol) in H₂O (7.0 ml) was placed in a 16 ml Teflon-lined stainless steel vessel and heated to 160 °C for 48 h, then cooled to room temperature at a rate of -5 °C/h. The solution was filtered and the colorless filtrate was allowed to stand at room temperature. Slow evaporation for about one week afforded colorless block crystals.