Potassium 2-[(2-carboxy­phen­yl)disulfan­yl]benzoate–2,2′-disulfanediyl­dibenzoic acid (1/1)

Arman, H.D.; Poplaukhin, P.; Tiekink, E.R.T.

doi:10.1107/S1600536809049824

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3202

doi:10.1107/S1600536809049824

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Potassium 2-[(2-carboxyphenyl)disulfanyl]benzoate–2,2′-disulfanediyldibenzoic acid (1/1)

Hadi D. Arman,^a Pavel Poplaukhin ^b and Edward R. T. Tiekink ^c ^*

^aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, ^bChemical Abstracts Service, 2540 Olentangy River Rd, Columbus, Ohio 43202, USA, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 20 November 2009; accepted 20 November 2009; online 25 November 2009)

In the title compound, K⁺·C₁₄H₉O₄S₂⁻·C₁₄H₁₀O₄S₂, the hydrogen 2,2′-dithiodibenzoate and 2,2′-disulfanediyldibenzoic acid species combine to provide an O₆S₂ donor set to the potassium cation based on a cubic geometry. K⋯S [3.1733 (7) and 3.5499 (8) Å] and K⋯O [2.6586 (16)–3.0661 (15) Å)] interactions, coupled with O—H⋯O hydrogen bonding, lead to the formation of supramolecular chains along [010].

Related literature

For terminology of co-crystals, see: Zukerman-Schpector & Tiekink (2008 ). For related studies on co-crystal formation with 2,2′-disulfanediyldibenzoic acid, see: Broker & Tiekink (2007 ); Broker et al. (2008 ).

Experimental

Crystal data

K⁺·C₁₄H₉O₄S₂⁻·C₁₄H₁₀O₄S₂
M_r = 650.81
Triclinic, $[P \overline 1]$
a = 11.1128 (14) Å
b = 12.1225 (15) Å
c = 12.5344 (12) Å
α = 65.501 (8)°
β = 64.216 (8)°
γ = 80.144 (10)°
V = 1383.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.55 mm⁻¹
T = 98 K
0.50 × 0.25 × 0.20 mm

Data collection

Rigaku AFC12K/SATURN724 diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.840, T_max = 1
10251 measured reflections
6302 independent reflections
5938 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.102
S = 1.07
6302 reflections
379 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1o⋯O1ⁱ	0.84	1.80	2.631 (2)	169
O6—H2o⋯O2ⁱⁱ	0.84	1.68	2.515 (2)	177
O8—H3o⋯O5ⁱ	0.84	1.88	2.704 (2)	167
Symmetry codes: (i) x, y-1, z; (ii) -x, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049824/hg2606sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049824/hg2606Isup2.hkl

checkCIF report

Comment top

The title compound, (I), a co-crystal of the potassium salt of hydrogen 2,2'-disulfanediyldibenzoate with 2,2'-disulfanediyldibenzoic acid (Zukerman-Schpector & Tiekink, 2008) was isolated during on-going studies into co-crystal formation of 2,2'-disulfanediyldibenzoic acid (Broker & Tiekink, 2007; Broker et al., 2008). The asymmetric unit, Fig. 1, comprises a potassium cation, a hydrogen 2,2'-disulfanediyldibenzoate anion and a neutral 2,2'-disulfanediyldibenzoic acid molecule. Confirmation of deprotonation of the C1-carboxylate is seen in the C1–O1 and C1–O2 bond distances of 1.251 (2) and 1.273 (2) Å, respectively, with their near equivalence contrasting the disparity in the C–O bond distances for the C14-, C15- and C-28 carboxylic acid groups where the C–O_carbonyl bonds (1.215 (2) to 1.234 (2) Å) are systematically shorter than the C–O_hydroxyl bonds (1.299 (2) to 1.328 (2) Å). The respective carboxylic acid groups are co-planar with the benzene rings to which they are bonded. By contrast, the C1-carboxylate group is somewhat twisted out of the plane as seen in the O1–C1–C2–C3 torsion angle of 160.18 (18) °. Both the hydrogen 2,2'-disulfanediyldibenzoate and 2,2'-disulfanediyldibenzoic acid species adopt the common L-conformation (Broker & Tiekink, 2007) as seen in the dihedral angles formed between the (C2–C7) and (C8–C13) rings of 78.65 (10) °, and between the (C16–C21) and (C22–C27) rings of 75.41 (11) °.

The K⁺ cation geometry is defined by six O atoms (range of K···O = 2.6586 (16) to 3.0661 (15) Å) and two S atoms (K···S = 3.1733 (7) and 3.5499 (8) Å). The coordination geometry is based on a cube, Fig. 2, with one face defined by the O1, O5, O3ⁱⁱ, and O7ⁱⁱ atoms, and the other by the S1ⁱ, S3¹, O2ⁱ, and O7ⁱ atoms; see the caption to Fig. 2 for symmetry operations. The dihedral angle formed between the two approximately square faces is 8.95 (4) °.

The K⁺ function as bridges between the 2,2'-disulfanediyldibenzoate and 2,2'-disulfanediyldibenzoic acid species to generate a supramolecular chain aligned along [0 1 0], Fig. 3. Stability to the chain is afforded by O–H···O hydrogen bonds, Table 1. The supramolecular chains are consolidated into the crystal structure by contacts of the type C–H···π: C25–H···Cg(C2–C7)ⁱⁱⁱ = 2.57 Å, C25···Cg(C2–C7)ⁱⁱⁱ = 3.456 (2) Å with an angle at H25 = 155 °; symmetry operation iii: x, y, -1 + z.

Related literature top

For terminology of co-crystals, see: Zukerman-Schpector & Tiekink (2008). For related studies on cocrystal formation with 2,2'-disulfanediyldibenzoic acid, see: Broker & Tiekink (2007); Broker et al. (2008).

Experimental top

2,2'-disulfanediyldibenzoic acid (306 mg, 1.00 mmol) and 85% potassium hydroxide (132 mg, 2.00 mmol) were dissolved in methanol (40 ml). The resulting cloudy solution was filtered and left to evaporate slowly. Colourless block-like crystals of (I) appeared in five days.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. Molecular structures of the asymmetric unit of (I), showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. The coordination environment for the K⁺ cation in (I), highlighting the approximately cubic geometry defined by an O₆S₂ donor set. Symmetry codes: i, -x, 1 - y, 1 - z; ii, x, 1 + y, z. Colour code: K, brown; S, yellow; and O, red.
	Fig. 3. Supramolecular chain in (I) oriented along [0 1 0]. Colour code: K, brown; S, yellow; O,red; N, blue; C, grey; and H, green. The O–H···O hydrogen bonds are shown as orange dashed lines.

Potassium 2-[(2-carboxyphenyl)disulfanyl]benzoate–2,2'-disulfanediyldibenzoic acid (1/1) top

Crystal data top

K⁺·C₁₄H₉O₄S₂⁻·C₁₄H₁₀O₄S₂	Z = 2
M_r = 650.81	F(000) = 668
Triclinic, P1	D_x = 1.562 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 11.1128 (14) Å	Cell parameters from 5714 reflections
b = 12.1225 (15) Å	θ = 2.7–40.6°
c = 12.5344 (12) Å	µ = 0.55 mm⁻¹
α = 65.501 (8)°	T = 98 K
β = 64.216 (8)°	Prism, colourless
γ = 80.144 (10)°	0.50 × 0.25 × 0.20 mm
V = 1383.5 (3) Å³

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	6302 independent reflections
Radiation source: fine-focus sealed tube	5938 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
T_min = 0.840, T_max = 1	k = −12→15
10251 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0443P)² + 0.8893P] where P = (F_o² + 2F_c²)/3
6302 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.39 e Å⁻³
3 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

K⁺·C₁₄H₉O₄S₂⁻·C₁₄H₁₀O₄S₂	γ = 80.144 (10)°
M_r = 650.81	V = 1383.5 (3) Å³
Triclinic, P1	Z = 2
a = 11.1128 (14) Å	Mo Kα radiation
b = 12.1225 (15) Å	µ = 0.55 mm⁻¹
c = 12.5344 (12) Å	T = 98 K
α = 65.501 (8)°	0.50 × 0.25 × 0.20 mm
β = 64.216 (8)°

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	6302 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5938 reflections with I > 2σ(I)
T_min = 0.840, T_max = 1	R_int = 0.030
10251 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	3 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.07	Δρ_max = 0.39 e Å⁻³
6302 reflections	Δρ_min = −0.43 e Å⁻³
379 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
K	0.10124 (4)	0.69989 (3)	0.47189 (4)	0.01869 (10)
S1	0.11089 (5)	0.14205 (4)	0.63434 (5)	0.01768 (11)
S2	0.14595 (5)	−0.02859 (4)	0.63245 (4)	0.01697 (11)
S3	0.18089 (5)	0.27372 (4)	0.26012 (5)	0.02144 (11)
S4	0.21527 (5)	0.10430 (4)	0.25588 (5)	0.02251 (12)
O1	0.18078 (14)	0.49091 (12)	0.62398 (14)	0.0211 (3)
O2	0.05044 (13)	0.37852 (12)	0.61416 (13)	0.0185 (3)
O3	0.15180 (14)	−0.25033 (11)	0.63792 (13)	0.0189 (3)
O4	0.10686 (16)	−0.42661 (12)	0.80702 (14)	0.0246 (3)
H1O	0.1205	−0.4501	0.7484	0.037*
O5	0.26289 (15)	0.60519 (12)	0.28654 (15)	0.0243 (3)
O6	0.12413 (14)	0.47773 (12)	0.30945 (13)	0.0195 (3)
H2O	0.0681	0.5271	0.3349	0.029*
O7	0.24704 (17)	−0.12001 (13)	0.26137 (15)	0.0295 (3)
O8	0.35737 (16)	−0.17734 (13)	0.09558 (15)	0.0264 (3)
H3O	0.3404	−0.2465	0.1547	0.040*
C1	0.16289 (19)	0.40409 (15)	0.60292 (17)	0.0155 (3)
C2	0.28063 (18)	0.32770 (16)	0.56010 (17)	0.0160 (3)
C3	0.27134 (19)	0.20991 (16)	0.56926 (18)	0.0173 (3)
C4	0.3891 (2)	0.14730 (18)	0.5273 (2)	0.0252 (4)
H4	0.3841	0.0671	0.5341	0.030*
C5	0.5130 (2)	0.20089 (19)	0.4760 (2)	0.0294 (5)
H5	0.5920	0.1574	0.4472	0.035*
C6	0.5225 (2)	0.31767 (19)	0.4663 (2)	0.0269 (4)
H6	0.6073	0.3545	0.4313	0.032*
C7	0.4064 (2)	0.37927 (17)	0.50859 (19)	0.0212 (4)
H7	0.4124	0.4591	0.5023	0.025*
C8	0.12319 (18)	−0.12228 (16)	0.79411 (17)	0.0161 (3)
C9	0.10333 (18)	−0.24877 (16)	0.84089 (17)	0.0157 (3)
C10	0.07086 (19)	−0.31939 (17)	0.97067 (18)	0.0196 (4)
H10	0.0549	−0.4039	1.0022	0.023*
C11	0.0616 (2)	−0.26811 (18)	1.05393 (19)	0.0226 (4)
H11	0.0371	−0.3163	1.1425	0.027*
C12	0.0886 (2)	−0.14551 (18)	1.00653 (19)	0.0224 (4)
H12	0.0863	−0.1105	1.0626	0.027*
C13	0.11874 (19)	−0.07327 (17)	0.87901 (19)	0.0200 (4)
H13	0.1367	0.0107	0.8486	0.024*
C14	0.12207 (18)	−0.30683 (16)	0.75195 (18)	0.0164 (3)
C15	0.24360 (19)	0.51477 (16)	0.27414 (17)	0.0172 (3)
C16	0.35667 (19)	0.44214 (16)	0.21775 (17)	0.0169 (3)
C17	0.34242 (19)	0.33352 (16)	0.20805 (18)	0.0176 (3)
C18	0.4573 (2)	0.27481 (17)	0.15355 (19)	0.0204 (4)
H18	0.4492	0.2016	0.1465	0.024*
C19	0.5836 (2)	0.32104 (18)	0.1093 (2)	0.0228 (4)
H19	0.6607	0.2793	0.0727	0.027*
C20	0.5976 (2)	0.42820 (19)	0.1182 (2)	0.0247 (4)
H20	0.6839	0.4605	0.0872	0.030*
C21	0.4851 (2)	0.48689 (17)	0.1724 (2)	0.0219 (4)
H21	0.4947	0.5598	0.1792	0.026*
C22	0.26830 (19)	0.12903 (17)	0.09047 (19)	0.0196 (4)
C23	0.31293 (19)	0.03064 (17)	0.05098 (19)	0.0201 (4)
C24	0.3623 (2)	0.05123 (19)	−0.0790 (2)	0.0243 (4)
H24	0.3940	−0.0151	−0.1055	0.029*
C25	0.3657 (2)	0.1666 (2)	−0.1700 (2)	0.0275 (4)
H25	0.4004	0.1799	−0.2583	0.033*
C26	0.3180 (2)	0.26238 (19)	−0.1302 (2)	0.0281 (4)
H26	0.3172	0.3415	−0.1916	0.034*
C27	0.2713 (2)	0.24465 (18)	−0.0023 (2)	0.0240 (4)
H27	0.2410	0.3119	0.0226	0.029*
C28	0.3029 (2)	−0.09482 (17)	0.1464 (2)	0.0212 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
K	0.0236 (2)	0.01461 (18)	0.0195 (2)	0.00072 (15)	−0.00917 (16)	−0.00773 (15)
S1	0.0179 (2)	0.0111 (2)	0.0223 (2)	0.00063 (16)	−0.00674 (18)	−0.00661 (17)
S2	0.0223 (2)	0.0113 (2)	0.0166 (2)	−0.00094 (16)	−0.00695 (18)	−0.00533 (16)
S3	0.0165 (2)	0.0181 (2)	0.0269 (3)	−0.00257 (17)	−0.00043 (19)	−0.01389 (19)
S4	0.0238 (2)	0.0162 (2)	0.0217 (2)	−0.00477 (18)	0.00022 (19)	−0.01007 (18)
O1	0.0246 (7)	0.0139 (6)	0.0254 (7)	0.0003 (5)	−0.0072 (6)	−0.0112 (5)
O2	0.0186 (6)	0.0169 (6)	0.0212 (7)	0.0016 (5)	−0.0065 (5)	−0.0104 (5)
O3	0.0248 (7)	0.0149 (6)	0.0165 (6)	−0.0021 (5)	−0.0063 (6)	−0.0068 (5)
O4	0.0392 (9)	0.0120 (6)	0.0212 (7)	−0.0032 (6)	−0.0102 (7)	−0.0058 (5)
O5	0.0239 (7)	0.0180 (6)	0.0305 (8)	−0.0013 (6)	−0.0049 (6)	−0.0148 (6)
O6	0.0183 (6)	0.0157 (6)	0.0236 (7)	0.0018 (5)	−0.0049 (6)	−0.0111 (5)
O7	0.0394 (9)	0.0165 (7)	0.0240 (8)	−0.0050 (6)	−0.0025 (7)	−0.0086 (6)
O8	0.0331 (8)	0.0183 (7)	0.0275 (8)	0.0024 (6)	−0.0093 (7)	−0.0125 (6)
C1	0.0210 (9)	0.0098 (7)	0.0126 (8)	−0.0003 (6)	−0.0047 (7)	−0.0035 (6)
C2	0.0185 (8)	0.0140 (8)	0.0144 (8)	−0.0004 (7)	−0.0046 (7)	−0.0064 (7)
C3	0.0180 (8)	0.0149 (8)	0.0171 (9)	−0.0009 (7)	−0.0045 (7)	−0.0067 (7)
C4	0.0208 (10)	0.0187 (9)	0.0338 (11)	0.0018 (7)	−0.0044 (8)	−0.0157 (8)
C5	0.0188 (10)	0.0246 (10)	0.0410 (13)	0.0030 (8)	−0.0038 (9)	−0.0192 (9)
C6	0.0184 (9)	0.0237 (10)	0.0316 (11)	−0.0032 (8)	−0.0023 (8)	−0.0114 (9)
C7	0.0225 (9)	0.0145 (8)	0.0233 (10)	−0.0014 (7)	−0.0054 (8)	−0.0078 (7)
C8	0.0157 (8)	0.0148 (8)	0.0154 (8)	−0.0003 (6)	−0.0044 (7)	−0.0057 (7)
C9	0.0152 (8)	0.0145 (8)	0.0158 (8)	−0.0008 (6)	−0.0049 (7)	−0.0056 (7)
C10	0.0185 (9)	0.0179 (8)	0.0164 (9)	−0.0034 (7)	−0.0034 (7)	−0.0037 (7)
C11	0.0211 (9)	0.0268 (10)	0.0142 (9)	0.0014 (8)	−0.0040 (7)	−0.0064 (7)
C12	0.0234 (9)	0.0273 (10)	0.0215 (10)	0.0064 (8)	−0.0097 (8)	−0.0157 (8)
C13	0.0213 (9)	0.0178 (8)	0.0222 (9)	0.0018 (7)	−0.0075 (8)	−0.0109 (7)
C14	0.0164 (8)	0.0126 (8)	0.0182 (9)	−0.0009 (6)	−0.0046 (7)	−0.0062 (7)
C15	0.0220 (9)	0.0125 (8)	0.0147 (8)	0.0006 (7)	−0.0056 (7)	−0.0050 (6)
C16	0.0197 (9)	0.0140 (8)	0.0149 (8)	0.0007 (7)	−0.0054 (7)	−0.0054 (7)
C17	0.0175 (8)	0.0167 (8)	0.0157 (8)	−0.0025 (7)	−0.0034 (7)	−0.0062 (7)
C18	0.0203 (9)	0.0175 (8)	0.0224 (9)	−0.0001 (7)	−0.0043 (8)	−0.0112 (7)
C19	0.0170 (9)	0.0250 (10)	0.0250 (10)	0.0032 (8)	−0.0043 (8)	−0.0139 (8)
C20	0.0175 (9)	0.0264 (10)	0.0303 (11)	−0.0014 (8)	−0.0073 (8)	−0.0130 (8)
C21	0.0225 (9)	0.0188 (9)	0.0256 (10)	−0.0018 (7)	−0.0081 (8)	−0.0105 (8)
C22	0.0168 (8)	0.0176 (8)	0.0232 (9)	−0.0028 (7)	−0.0037 (7)	−0.0102 (7)
C23	0.0197 (9)	0.0175 (9)	0.0235 (10)	−0.0011 (7)	−0.0064 (8)	−0.0102 (7)
C24	0.0266 (10)	0.0251 (10)	0.0265 (10)	0.0004 (8)	−0.0112 (9)	−0.0143 (8)
C25	0.0314 (11)	0.0294 (10)	0.0245 (10)	−0.0015 (9)	−0.0125 (9)	−0.0110 (9)
C26	0.0333 (11)	0.0213 (9)	0.0319 (11)	−0.0007 (8)	−0.0184 (10)	−0.0063 (8)
C27	0.0240 (10)	0.0176 (9)	0.0314 (11)	0.0005 (7)	−0.0112 (9)	−0.0105 (8)
C28	0.0228 (9)	0.0169 (9)	0.0262 (10)	−0.0030 (7)	−0.0079 (8)	−0.0113 (8)

Geometric parameters (Å, º) top

K—O7ⁱ	2.6586 (16)	C5—H5	0.9500
K—O3ⁱ	2.6806 (14)	C6—C7	1.381 (3)
K—O1	2.7436 (15)	C6—H6	0.9500
K—O5	2.7960 (15)	C7—H7	0.9500
K—O2ⁱⁱ	2.8086 (14)	C8—C13	1.399 (2)
K—O6ⁱⁱ	3.0661 (15)	C8—C9	1.415 (2)
K—S1ⁱⁱ	3.1733 (7)	C9—C10	1.396 (3)
K—S3ⁱⁱ	3.5499 (8)	C9—C14	1.477 (2)
S1—C3	1.7893 (19)	C10—C11	1.382 (3)
S1—S2	2.0465 (7)	C10—H10	0.9500
S1—Kⁱⁱ	3.1733 (7)	C11—C12	1.384 (3)
S2—C8	1.7899 (19)	C11—H11	0.9500
S3—C17	1.7910 (19)	C12—C13	1.381 (3)
S3—S4	2.0423 (7)	C12—H12	0.9500
S3—Kⁱⁱ	3.5499 (8)	C13—H13	0.9500
S4—C22	1.794 (2)	C15—C16	1.489 (2)
O1—C1	1.251 (2)	C16—C21	1.399 (3)
O2—C1	1.273 (2)	C16—C17	1.412 (2)
O2—Kⁱⁱ	2.8086 (14)	C17—C18	1.392 (3)
O3—C14	1.215 (2)	C18—C19	1.387 (3)
O3—Kⁱⁱⁱ	2.6806 (14)	C18—H18	0.9500
O4—C14	1.328 (2)	C19—C20	1.389 (3)
O4—H1O	0.8400	C19—H19	0.9500
O5—C15	1.234 (2)	C20—C21	1.374 (3)
O6—C15	1.299 (2)	C20—H20	0.9500
O6—Kⁱⁱ	3.0661 (15)	C21—H21	0.9500
O6—H2O	0.8401	C22—C27	1.396 (3)
O7—C28	1.216 (3)	C22—C23	1.410 (3)
O7—Kⁱⁱⁱ	2.6586 (16)	C23—C24	1.397 (3)
O8—C28	1.326 (2)	C23—C28	1.480 (3)
O8—H3O	0.8400	C24—C25	1.384 (3)
C1—C2	1.498 (2)	C24—H24	0.9500
C2—C7	1.393 (3)	C25—C26	1.385 (3)
C2—C3	1.402 (2)	C25—H25	0.9500
C3—C4	1.399 (3)	C26—C27	1.383 (3)
C4—C5	1.386 (3)	C26—H26	0.9500
C4—H4	0.9500	C27—H27	0.9500
C5—C6	1.389 (3)

O7ⁱ—K—O3ⁱ	96.77 (5)	C6—C5—H5	119.8
O7ⁱ—K—O1	129.86 (5)	C7—C6—C5	118.79 (19)
O3ⁱ—K—O1	71.45 (4)	C7—C6—H6	120.6
O7ⁱ—K—O5	71.64 (5)	C5—C6—H6	120.6
O3ⁱ—K—O5	131.40 (5)	C6—C7—C2	121.89 (17)
O1—K—O5	80.67 (4)	C6—C7—H7	119.1
O7ⁱ—K—O2ⁱⁱ	102.50 (5)	C2—C7—H7	119.1
O3ⁱ—K—O2ⁱⁱ	156.62 (4)	C13—C8—C9	118.12 (17)
O1—K—O2ⁱⁱ	104.90 (4)	C13—C8—S2	121.69 (14)
O5—K—O2ⁱⁱ	68.35 (4)	C9—C8—S2	120.13 (14)
O7ⁱ—K—O6ⁱⁱ	165.18 (5)	C10—C9—C8	119.83 (17)
O3ⁱ—K—O6ⁱⁱ	91.66 (4)	C10—C9—C14	119.97 (16)
O1—K—O6ⁱⁱ	64.50 (4)	C8—C9—C14	120.16 (16)
O5—K—O6ⁱⁱ	111.36 (4)	C11—C10—C9	120.93 (18)
O2ⁱⁱ—K—O6ⁱⁱ	66.83 (4)	C11—C10—H10	119.5
O7ⁱ—K—S1ⁱⁱ	76.34 (4)	C9—C10—H10	119.5
O3ⁱ—K—S1ⁱⁱ	119.10 (3)	C10—C11—C12	119.14 (18)
O1—K—S1ⁱⁱ	152.42 (3)	C10—C11—H11	120.4
O5—K—S1ⁱⁱ	104.08 (4)	C12—C11—H11	120.4
O2ⁱⁱ—K—S1ⁱⁱ	54.55 (3)	C13—C12—C11	121.05 (18)
O6ⁱⁱ—K—S1ⁱⁱ	88.92 (3)	C13—C12—H12	119.5
O7ⁱ—K—C1	132.30 (5)	C11—C12—H12	119.5
O3ⁱ—K—C1	91.89 (4)	C12—C13—C8	120.76 (18)
O1—K—C1	20.67 (4)	C12—C13—H13	119.6
O5—K—C1	67.73 (4)	C8—C13—H13	119.6
O2ⁱⁱ—K—C1	84.91 (4)	O3—C14—O4	122.96 (17)
O6ⁱⁱ—K—C1	59.17 (4)	O3—C14—C9	122.95 (16)
S1ⁱⁱ—K—C1	137.02 (4)	O4—C14—C9	114.07 (16)
O7ⁱ—K—S3ⁱⁱ	126.93 (4)	O5—C15—O6	122.01 (17)
O3ⁱ—K—S3ⁱⁱ	63.62 (3)	O5—C15—C16	121.54 (17)
O1—K—S3ⁱⁱ	92.08 (3)	O6—C15—C16	116.45 (15)
O5—K—S3ⁱⁱ	158.01 (3)	C21—C16—C17	119.09 (17)
O2ⁱⁱ—K—S3ⁱⁱ	93.93 (3)	C21—C16—C15	116.14 (16)
O6ⁱⁱ—K—S3ⁱⁱ	47.48 (3)	C17—C16—C15	124.77 (17)
S1ⁱⁱ—K—S3ⁱⁱ	73.298 (18)	C18—C17—C16	118.50 (17)
C1—K—S3ⁱⁱ	98.84 (4)	C18—C17—S3	120.19 (14)
C3—S1—S2	106.32 (6)	C16—C17—S3	121.29 (14)
C3—S1—Kⁱⁱ	117.10 (6)	C19—C18—C17	121.31 (17)
S2—S1—Kⁱⁱ	117.18 (2)	C19—C18—H18	119.3
C8—S2—S1	103.19 (6)	C17—C18—H18	119.3
C17—S3—S4	105.25 (6)	C18—C19—C20	120.18 (18)
C17—S3—Kⁱⁱ	122.79 (6)	C18—C19—H19	119.9
S4—S3—Kⁱⁱ	115.73 (3)	C20—C19—H19	119.9
C22—S4—S3	104.75 (7)	C21—C20—C19	119.20 (19)
C1—O1—K	108.58 (11)	C21—C20—H20	120.4
C1—O2—Kⁱⁱ	150.37 (12)	C19—C20—H20	120.4
C14—O3—Kⁱⁱⁱ	129.98 (12)	C20—C21—C16	121.71 (18)
C14—O4—H1O	106.2	C20—C21—H21	119.1
C15—O5—K	128.86 (13)	C16—C21—H21	119.1
C15—O6—Kⁱⁱ	143.84 (11)	C27—C22—C23	118.46 (18)
C15—O6—H2O	109.1	C27—C22—S4	121.72 (15)
Kⁱⁱ—O6—H2O	80.5 (18)	C23—C22—S4	119.78 (15)
C28—O7—Kⁱⁱⁱ	138.62 (13)	C24—C23—C22	119.70 (18)
C28—O8—H3O	108.8	C24—C23—C28	119.61 (17)
O1—C1—O2	123.42 (17)	C22—C23—C28	120.65 (18)
O1—C1—C2	118.14 (17)	C25—C24—C23	121.10 (19)
O2—C1—C2	118.43 (15)	C25—C24—H24	119.5
O1—C1—K	50.75 (9)	C23—C24—H24	119.5
O2—C1—K	89.28 (10)	C24—C25—C26	118.9 (2)
C2—C1—K	132.00 (11)	C24—C25—H25	120.5
C7—C2—C3	119.20 (17)	C26—C25—H25	120.5
C7—C2—C1	116.45 (16)	C27—C26—C25	121.0 (2)
C3—C2—C1	124.35 (16)	C27—C26—H26	119.5
C4—C3—C2	118.82 (17)	C25—C26—H26	119.5
C4—C3—S1	121.17 (14)	C26—C27—C22	120.77 (19)
C2—C3—S1	120.00 (14)	C26—C27—H27	119.6
C5—C4—C3	120.82 (18)	C22—C27—H27	119.6
C5—C4—H4	119.6	O7—C28—O8	123.05 (18)
C3—C4—H4	119.6	O7—C28—C23	122.69 (18)
C4—C5—C6	120.47 (19)	O8—C28—C23	114.24 (17)
C4—C5—H5	119.8

C3—S1—S2—C8	99.20 (9)	C5—C6—C7—C2	−0.1 (3)
Kⁱⁱ—S1—S2—C8	−127.65 (6)	C3—C2—C7—C6	−0.1 (3)
C17—S3—S4—C22	−80.05 (9)	C1—C2—C7—C6	179.66 (18)
Kⁱⁱ—S3—S4—C22	140.98 (7)	S1—S2—C8—C13	−14.36 (17)
O7ⁱ—K—O1—C1	−105.72 (13)	S1—S2—C8—C9	162.90 (14)
O3ⁱ—K—O1—C1	171.05 (13)	C13—C8—C9—C10	4.5 (3)
O5—K—O1—C1	−49.30 (12)	S2—C8—C9—C10	−172.87 (14)
O2ⁱⁱ—K—O1—C1	15.19 (13)	C13—C8—C9—C14	−173.11 (17)
O6ⁱⁱ—K—O1—C1	69.87 (12)	S2—C8—C9—C14	9.5 (2)
S1ⁱⁱ—K—O1—C1	53.30 (16)	C8—C9—C10—C11	−1.9 (3)
S3ⁱⁱ—K—O1—C1	109.82 (12)	C14—C9—C10—C11	175.66 (17)
O7ⁱ—K—O5—C15	−153.39 (17)	C9—C10—C11—C12	−1.7 (3)
O3ⁱ—K—O5—C15	123.90 (16)	C10—C11—C12—C13	2.8 (3)
O1—K—O5—C15	68.98 (16)	C11—C12—C13—C8	−0.2 (3)
O2ⁱⁱ—K—O5—C15	−41.24 (16)	C9—C8—C13—C12	−3.5 (3)
O6ⁱⁱ—K—O5—C15	11.17 (17)	S2—C8—C13—C12	173.84 (15)
S1ⁱⁱ—K—O5—C15	−83.26 (16)	Kⁱⁱⁱ—O3—C14—O4	29.1 (3)
C1—K—O5—C15	52.17 (16)	Kⁱⁱⁱ—O3—C14—C9	−152.68 (13)
S3ⁱⁱ—K—O5—C15	−3.0 (2)	C10—C9—C14—O3	−179.17 (18)
K—O1—C1—O2	−56.0 (2)	C8—C9—C14—O3	−1.6 (3)
K—O1—C1—C2	122.87 (14)	C10—C9—C14—O4	−0.8 (2)
Kⁱⁱ—O2—C1—O1	141.59 (18)	C8—C9—C14—O4	176.81 (17)
Kⁱⁱ—O2—C1—C2	−37.3 (3)	K—O5—C15—O6	30.2 (3)
Kⁱⁱ—O2—C1—K	101.6 (2)	K—O5—C15—C16	−149.79 (13)
O7ⁱ—K—C1—O1	92.45 (13)	Kⁱⁱ—O6—C15—O5	−96.3 (2)
O3ⁱ—K—C1—O1	−8.48 (12)	Kⁱⁱ—O6—C15—C16	83.7 (2)
O5—K—C1—O1	126.07 (13)	O5—C15—C16—C21	−4.0 (3)
O2ⁱⁱ—K—C1—O1	−165.27 (12)	O6—C15—C16—C21	176.03 (17)
O6ⁱⁱ—K—C1—O1	−99.29 (13)	O5—C15—C16—C17	175.73 (18)
S1ⁱⁱ—K—C1—O1	−147.01 (11)	O6—C15—C16—C17	−4.2 (3)
S3ⁱⁱ—K—C1—O1	−72.07 (12)	C21—C16—C17—C18	0.1 (3)
O7ⁱ—K—C1—O2	−131.37 (10)	C15—C16—C17—C18	−179.68 (17)
O3ⁱ—K—C1—O2	127.70 (10)	C21—C16—C17—S3	−178.20 (14)
O1—K—C1—O2	136.18 (18)	C15—C16—C17—S3	2.1 (3)
O5—K—C1—O2	−97.75 (11)	S4—S3—C17—C18	11.76 (17)
O2ⁱⁱ—K—C1—O2	−29.09 (12)	Kⁱⁱ—S3—C17—C18	147.07 (13)
O6ⁱⁱ—K—C1—O2	36.89 (9)	S4—S3—C17—C16	−170.00 (14)
S1ⁱⁱ—K—C1—O2	−10.83 (13)	Kⁱⁱ—S3—C17—C16	−34.69 (18)
S3ⁱⁱ—K—C1—O2	64.11 (10)	C16—C17—C18—C19	−0.1 (3)
O7ⁱ—K—C1—C2	−2.37 (18)	S3—C17—C18—C19	178.21 (16)
O3ⁱ—K—C1—C2	−103.30 (15)	C17—C18—C19—C20	−0.3 (3)
O1—K—C1—C2	−94.8 (2)	C18—C19—C20—C21	0.6 (3)
O5—K—C1—C2	31.25 (15)	C19—C20—C21—C16	−0.6 (3)
O2ⁱⁱ—K—C1—C2	99.91 (15)	C17—C16—C21—C20	0.3 (3)
O6ⁱⁱ—K—C1—C2	165.89 (17)	C15—C16—C21—C20	−179.95 (18)
S1ⁱⁱ—K—C1—C2	118.17 (15)	S3—S4—C22—C27	−3.69 (18)
S3ⁱⁱ—K—C1—C2	−166.89 (15)	S3—S4—C22—C23	173.96 (14)
O1—C1—C2—C7	−19.6 (2)	C27—C22—C23—C24	1.9 (3)
O2—C1—C2—C7	159.39 (17)	S4—C22—C23—C24	−175.88 (15)
K—C1—C2—C7	41.5 (2)	C27—C22—C23—C28	−175.62 (18)
O1—C1—C2—C3	160.18 (18)	S4—C22—C23—C28	6.6 (3)
O2—C1—C2—C3	−20.8 (3)	C22—C23—C24—C25	−1.3 (3)
K—C1—C2—C3	−138.76 (15)	C28—C23—C24—C25	176.20 (19)
C7—C2—C3—C4	0.6 (3)	C23—C24—C25—C26	−0.7 (3)
C1—C2—C3—C4	−179.18 (18)	C24—C25—C26—C27	2.1 (3)
C7—C2—C3—S1	−179.68 (14)	C25—C26—C27—C22	−1.5 (3)
C1—C2—C3—S1	0.6 (3)	C23—C22—C27—C26	−0.5 (3)
S2—S1—C3—C4	0.94 (18)	S4—C22—C27—C26	177.21 (16)
Kⁱⁱ—S1—C3—C4	−132.26 (15)	Kⁱⁱⁱ—O7—C28—O8	−32.8 (3)
S2—S1—C3—C2	−178.79 (13)	Kⁱⁱⁱ—O7—C28—C23	145.73 (16)
Kⁱⁱ—S1—C3—C2	48.01 (17)	C24—C23—C28—O7	−171.4 (2)
C2—C3—C4—C5	−0.8 (3)	C22—C23—C28—O7	6.1 (3)
S1—C3—C4—C5	179.44 (17)	C24—C23—C28—O8	7.2 (3)
C3—C4—C5—C6	0.6 (4)	C22—C23—C28—O8	−175.31 (18)
C4—C5—C6—C7	−0.1 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1o···O1ⁱⁱⁱ	0.84	1.80	2.631 (2)	169
O6—H2o···O2ⁱⁱ	0.84	1.68	2.515 (2)	177
O8—H3o···O5ⁱⁱⁱ	0.84	1.88	2.704 (2)	167

Symmetry codes: (ii) −x, −y+1, −z+1; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	K⁺·C₁₄H₉O₄S₂⁻·C₁₄H₁₀O₄S₂
M_r	650.81
Crystal system, space group	Triclinic, P1
Temperature (K)	98
a, b, c (Å)	11.1128 (14), 12.1225 (15), 12.5344 (12)
α, β, γ (°)	65.501 (8), 64.216 (8), 80.144 (10)
V (Å³)	1383.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.55
Crystal size (mm)	0.50 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku AFC12K/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.840, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	10251, 6302, 5938
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.102, 1.07
No. of reflections	6302
No. of parameters	379
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.43

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1o···O1ⁱ	0.84	1.80	2.631 (2)	169
O6—H2o···O2ⁱⁱ	0.84	1.68	2.515 (2)	177
O8—H3o···O5ⁱ	0.84	1.88	2.704 (2)	167

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

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Broker, G. A., Bettens, R. P. A. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 879–887. Web of Science CSD CrossRef CAS Google Scholar
Broker, G. A. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 1096–1109. Web of Science CSD CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
Zukerman-Schpector, J. & Tiekink, E. R. T. (2008). Z. Kristallogr. 223, 233–234. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 12| December 2009| Page o3202

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Potassium 2-[(2-carb­oxy­phen­yl)disulfan­yl]benzoate–2,2′-disulfanediyl­di­benzoic acid (1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

Potassium 2-[(2-carboxyphenyl)disulfanyl]benzoate–2,2′-disulfanediyldibenzoic acid (1/1)