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

Wang, G.-Y.

doi:10.1107/S1600536811025694

organic compounds

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Volume 67| Part 8| August 2011| Page o1923

doi:10.1107/S1600536811025694

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

Guang-Yin Wang ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou, Shandong 253023, People's Republic of China
^*Correspondence e-mail: dzgywang@126.com

(Received 24 June 2011; accepted 29 June 2011; online 6 July 2011)

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, C 2/c
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[F² > 2σ(F²)] = 0.043
wR(F²) = 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

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
Symmetry codes: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) x, y-1, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025694/zs2125sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

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

Figures top

	Fig. 1. Atom numbering scheme and anisotropic displacement ellipsoid plot of (I) at the 50% probability level. H atoms are represented by circles of arbitrary size. Symmetry codes: (i) -x + 2, y, -z + 1/2; (ii) -x, -y + 2, -z.
	Fig. 2. The one-dimensional zigzag chain structure of the title compound. Non-associative H atoms are omitted and hydrogen bonds are shown as dashed lines.
	Fig. 3. The packing diagram of the title compound showing C—H···π interactions.

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

Crystal data top

C₁₀H₈N₂S₂·C₁₀H₁₀O₆	F(000) = 928
M_r = 446.50	D_x = 1.461 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1634 reflections
a = 14.331 (1) Å	θ = 2.8–25.2°
b = 5.057 (1) Å	µ = 0.30 mm⁻¹
c = 28.003 (3) Å	T = 296 K
β = 90.200 (5)°	Block, colorless
V = 2029.4 (5) Å³	0.31 × 0.21 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	1761 independent reflections
Radiation source: fine-focus sealed tube	1450 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→16
T_min = 0.912, T_max = 0.974	k = −5→5
4893 measured reflections	l = −33→32

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0548P)² + 1.8236P] where P = (F_o² + 2F_c²)/3
1761 reflections	(Δ/σ)_max < 0.001
137 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₀H₈N₂S₂·C₁₀H₁₀O₆	V = 2029.4 (5) Å³
M_r = 446.50	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 14.331 (1) Å	µ = 0.30 mm⁻¹
b = 5.057 (1) Å	T = 296 K
c = 28.003 (3) Å	0.31 × 0.21 × 0.09 mm
β = 90.200 (5)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1761 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1450 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.974	R_int = 0.026
4893 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	Δρ_max = 0.62 e Å⁻³
1761 reflections	Δρ_min = −0.29 e Å⁻³
137 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.92972 (4)	−0.22476 (13)	0.24909 (2)	0.0514 (2)
O1	0.07968 (11)	0.6344 (3)	0.06109 (5)	0.0485 (4)
O2	0.15067 (12)	0.2818 (4)	0.12321 (6)	0.0596 (5)
N1	0.83733 (14)	0.3882 (5)	0.14055 (7)	0.0543 (6)
O3	0.26328 (12)	0.1757 (4)	0.07197 (7)	0.0683 (6)
H3	0.2843	0.0923	0.0947	0.102*
C8	0.04234 (15)	0.8125 (4)	0.02905 (8)	0.0389 (5)
C9	−0.02803 (15)	0.9711 (5)	0.04649 (8)	0.0440 (6)
H9	−0.0471	0.9519	0.0780	0.053*
C7	0.15542 (15)	0.4802 (5)	0.04525 (8)	0.0465 (6)
H7A	0.2061	0.5945	0.0353	0.056*
H7B	0.1364	0.3737	0.0181	0.056*
C3	0.89942 (16)	0.0216 (4)	0.20664 (8)	0.0425 (5)
C6	0.18774 (15)	0.3037 (5)	0.08524 (9)	0.0462 (6)
C1	0.92798 (17)	0.3451 (5)	0.14718 (8)	0.0517 (6)
H1	0.9703	0.4408	0.1289	0.062*
C2	0.96216 (16)	0.1654 (5)	0.17981 (8)	0.0476 (6)
H2	1.0261	0.1414	0.1837	0.057*
C10	−0.07061 (15)	1.1580 (5)	0.01785 (8)	0.0443 (6)
H10	−0.1181	1.2636	0.0300	0.053*
C4	0.80519 (17)	0.0660 (6)	0.19985 (10)	0.0584 (7)
H4	0.7612	−0.0283	0.2173	0.070*
C5	0.77771 (19)	0.2495 (6)	0.16724 (11)	0.0639 (8)
H5	0.7142	0.2800	0.1633	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0554 (4)	0.0495 (4)	0.0492 (4)	−0.0077 (3)	−0.0039 (3)	0.0034 (3)
O1	0.0518 (10)	0.0482 (10)	0.0455 (9)	0.0114 (8)	0.0044 (7)	0.0065 (8)
O2	0.0509 (10)	0.0769 (13)	0.0511 (10)	0.0127 (9)	0.0051 (8)	0.0143 (9)
N1	0.0542 (13)	0.0617 (14)	0.0470 (11)	0.0169 (11)	−0.0012 (9)	0.0002 (10)
O3	0.0555 (11)	0.0901 (15)	0.0593 (11)	0.0314 (10)	0.0075 (9)	0.0199 (10)
C8	0.0398 (12)	0.0344 (12)	0.0426 (12)	−0.0008 (9)	−0.0022 (9)	0.0013 (9)
C9	0.0490 (13)	0.0446 (14)	0.0384 (12)	0.0034 (11)	0.0044 (10)	0.0003 (10)
C7	0.0410 (12)	0.0475 (15)	0.0508 (13)	0.0035 (10)	0.0000 (10)	0.0048 (11)
C3	0.0492 (13)	0.0423 (13)	0.0361 (11)	0.0021 (10)	−0.0012 (9)	−0.0069 (10)
C6	0.0397 (13)	0.0484 (14)	0.0504 (14)	−0.0009 (11)	−0.0047 (11)	0.0023 (11)
C1	0.0531 (15)	0.0570 (16)	0.0451 (13)	0.0090 (12)	0.0057 (11)	0.0037 (12)
C2	0.0424 (13)	0.0553 (15)	0.0452 (13)	0.0083 (11)	0.0005 (10)	0.0001 (11)
C10	0.0426 (12)	0.0420 (13)	0.0481 (13)	0.0054 (10)	0.0044 (10)	−0.0011 (10)
C4	0.0454 (14)	0.0656 (18)	0.0643 (16)	−0.0013 (13)	0.0037 (12)	0.0045 (14)
C5	0.0468 (15)	0.075 (2)	0.0701 (18)	0.0106 (14)	−0.0039 (13)	0.0013 (16)

Geometric parameters (Å, º) top

S1—C3	1.775 (2)	C7—C6	1.504 (3)
S1—S1ⁱ	2.0150 (14)	C7—H7A	0.9700
O1—C8	1.378 (3)	C7—H7B	0.9700
O1—C7	1.409 (3)	C3—C2	1.381 (3)
O2—C6	1.195 (3)	C3—C4	1.381 (3)
N1—C1	1.330 (3)	C1—C2	1.378 (3)
N1—C5	1.336 (4)	C1—H1	0.9300
O3—C6	1.316 (3)	C2—H2	0.9300
O3—H3	0.8200	C10—C8ⁱⁱ	1.384 (3)
C8—C9	1.379 (3)	C10—H10	0.9300
C8—C10ⁱⁱ	1.384 (3)	C4—C5	1.359 (4)
C9—C10	1.380 (3)	C4—H4	0.9300
C9—H9	0.9300	C5—H5	0.9300

C3—S1—S1ⁱ	105.02 (8)	O2—C6—O3	125.0 (2)
C8—O1—C7	117.02 (17)	O2—C6—C7	125.5 (2)
C1—N1—C5	117.5 (2)	O3—C6—C7	109.5 (2)
C6—O3—H3	109.5	N1—C1—C2	123.1 (2)
C9—C8—O1	115.61 (19)	N1—C1—H1	118.5
C9—C8—C10ⁱⁱ	119.4 (2)	C2—C1—H1	118.5
O1—C8—C10ⁱⁱ	125.0 (2)	C1—C2—C3	118.5 (2)
C8—C9—C10	121.0 (2)	C1—C2—H2	120.7
C8—C9—H9	119.5	C3—C2—H2	120.7
C10—C9—H9	119.5	C9—C10—C8ⁱⁱ	119.7 (2)
O1—C7—C6	109.23 (19)	C9—C10—H10	120.2
O1—C7—H7A	109.8	C8ⁱⁱ—C10—H10	120.2
C6—C7—H7A	109.8	C5—C4—C3	119.0 (2)
O1—C7—H7B	109.8	C5—C4—H4	120.5
C6—C7—H7B	109.8	C3—C4—H4	120.5
H7A—C7—H7B	108.3	N1—C5—C4	123.4 (2)
C2—C3—C4	118.5 (2)	N1—C5—H5	118.3
C2—C3—S1	125.16 (18)	C4—C5—H5	118.3
C4—C3—S1	116.30 (18)

C7—O1—C8—C9	−176.4 (2)	C5—N1—C1—C2	0.3 (4)
C7—O1—C8—C10ⁱⁱ	3.2 (3)	N1—C1—C2—C3	0.5 (4)
O1—C8—C9—C10	179.7 (2)	C4—C3—C2—C1	−0.5 (3)
C10ⁱⁱ—C8—C9—C10	0.1 (4)	S1—C3—C2—C1	178.12 (18)
C8—O1—C7—C6	178.70 (18)	C8—C9—C10—C8ⁱⁱ	−0.1 (4)
S1ⁱ—S1—C3—C2	3.2 (2)	C2—C3—C4—C5	−0.2 (4)
S1ⁱ—S1—C3—C4	−178.13 (17)	S1—C3—C4—C5	−179.0 (2)
O1—C7—C6—O2	5.5 (3)	C1—N1—C5—C4	−1.1 (4)
O1—C7—C6—O3	−174.7 (2)	C3—C4—C5—N1	1.1 (4)

Symmetry codes: (i) −x+2, y, −z+1/2; (ii) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

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···N1ⁱⁱⁱ	0.82	1.81	2.629 (3)	174
C7—H7B···Cg1^iv	0.97	2.76	3.528 (2)	136

Symmetry codes: (iii) x−1/2, y−1/2, z; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂S₂·C₁₀H₁₀O₆
M_r	446.50
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	14.331 (1), 5.057 (1), 28.003 (3)
β (°)	90.200 (5)
V (Å³)	2029.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.31 × 0.21 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.912, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	4893, 1761, 1450
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.114, 1.05
No. of reflections	1761
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x−1/2, y−1/2, z; (ii) x, y−1, z.

Acknowledgements

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

References

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