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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Zukerman-Schpector, J. & Tiekink, E. R. T. (2008). Z. Kristallogr. 223, 233-234.]). For related studies on co-crystal formation with 2,2′-disulfanediyl­dibenzoic acid, see: Broker & Tiekink (2007[Broker, G. A. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 1096-1109.]); Broker et al. (2008[Broker, G. A., Bettens, R. P. A. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 879-887.]).

[Scheme 1]

Experimental

Crystal data
  • K+·C14H9O4S2·C14H10O4S2

  • Mr = 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.840, Tmax = 1

  • 10251 measured reflections

  • 6302 independent reflections

  • 5938 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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–Ocarbonyl bonds (1.215 (2) to 1.234 (2) Å) are systematically shorter than the C–Ohydroxyl 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.

Refinement top

The C-bound H-atoms were placed in calculated positions (C–H 0.95 Å) and were included in the refinement in the riding model approximation with Uiso(H) set to 1.2Ueq(C). The O-bound H-atoms were located in a difference Fourier map and refined with an O–H restraint of 0.840±0.001 Å, and with Uiso(H) = 1.5Ueq(O).

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
[Figure 1] Fig. 1. Molecular structures of the asymmetric unit of (I), showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] 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.
[Figure 3] 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·C14H10O4S2Z = 2
Mr = 650.81F(000) = 668
Triclinic, P1Dx = 1.562 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 11.1128 (14) ÅCell parameters from 5714 reflections
b = 12.1225 (15) Åθ = 2.7–40.6°
c = 12.5344 (12) ŵ = 0.55 mm1
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 tube5938 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1414
Tmin = 0.840, Tmax = 1k = 1215
10251 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0443P)2 + 0.8893P]
where P = (Fo2 + 2Fc2)/3
6302 reflections(Δ/σ)max = 0.001
379 parametersΔρmax = 0.39 e Å3
3 restraintsΔρmin = 0.43 e Å3
Crystal data top
K+·C14H9O4S2·C14H10O4S2γ = 80.144 (10)°
Mr = 650.81V = 1383.5 (3) Å3
Triclinic, P1Z = 2
a = 11.1128 (14) ÅMo Kα radiation
b = 12.1225 (15) ŵ = 0.55 mm1
c = 12.5344 (12) ÅT = 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)
Tmin = 0.840, Tmax = 1Rint = 0.030
10251 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0413 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.07Δρmax = 0.39 e Å3
6302 reflectionsΔρmin = 0.43 e Å3
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
xyzUiso*/Ueq
K0.10124 (4)0.69989 (3)0.47189 (4)0.01869 (10)
S10.11089 (5)0.14205 (4)0.63434 (5)0.01768 (11)
S20.14595 (5)0.02859 (4)0.63245 (4)0.01697 (11)
S30.18089 (5)0.27372 (4)0.26012 (5)0.02144 (11)
S40.21527 (5)0.10430 (4)0.25588 (5)0.02251 (12)
O10.18078 (14)0.49091 (12)0.62398 (14)0.0211 (3)
O20.05044 (13)0.37852 (12)0.61416 (13)0.0185 (3)
O30.15180 (14)0.25033 (11)0.63792 (13)0.0189 (3)
O40.10686 (16)0.42661 (12)0.80702 (14)0.0246 (3)
H1O0.12050.45010.74840.037*
O50.26289 (15)0.60519 (12)0.28654 (15)0.0243 (3)
O60.12413 (14)0.47773 (12)0.30945 (13)0.0195 (3)
H2O0.06810.52710.33490.029*
O70.24704 (17)0.12001 (13)0.26137 (15)0.0295 (3)
O80.35737 (16)0.17734 (13)0.09558 (15)0.0264 (3)
H3O0.34040.24650.15470.040*
C10.16289 (19)0.40409 (15)0.60292 (17)0.0155 (3)
C20.28063 (18)0.32770 (16)0.56010 (17)0.0160 (3)
C30.27134 (19)0.20991 (16)0.56926 (18)0.0173 (3)
C40.3891 (2)0.14730 (18)0.5273 (2)0.0252 (4)
H40.38410.06710.53410.030*
C50.5130 (2)0.20089 (19)0.4760 (2)0.0294 (5)
H50.59200.15740.44720.035*
C60.5225 (2)0.31767 (19)0.4663 (2)0.0269 (4)
H60.60730.35450.43130.032*
C70.4064 (2)0.37927 (17)0.50859 (19)0.0212 (4)
H70.41240.45910.50230.025*
C80.12319 (18)0.12228 (16)0.79411 (17)0.0161 (3)
C90.10333 (18)0.24877 (16)0.84089 (17)0.0157 (3)
C100.07086 (19)0.31939 (17)0.97067 (18)0.0196 (4)
H100.05490.40391.00220.023*
C110.0616 (2)0.26811 (18)1.05393 (19)0.0226 (4)
H110.03710.31631.14250.027*
C120.0886 (2)0.14551 (18)1.00653 (19)0.0224 (4)
H120.08630.11051.06260.027*
C130.11874 (19)0.07327 (17)0.87901 (19)0.0200 (4)
H130.13670.01070.84860.024*
C140.12207 (18)0.30683 (16)0.75195 (18)0.0164 (3)
C150.24360 (19)0.51477 (16)0.27414 (17)0.0172 (3)
C160.35667 (19)0.44214 (16)0.21775 (17)0.0169 (3)
C170.34242 (19)0.33352 (16)0.20805 (18)0.0176 (3)
C180.4573 (2)0.27481 (17)0.15355 (19)0.0204 (4)
H180.44920.20160.14650.024*
C190.5836 (2)0.32104 (18)0.1093 (2)0.0228 (4)
H190.66070.27930.07270.027*
C200.5976 (2)0.42820 (19)0.1182 (2)0.0247 (4)
H200.68390.46050.08720.030*
C210.4851 (2)0.48689 (17)0.1724 (2)0.0219 (4)
H210.49470.55980.17920.026*
C220.26830 (19)0.12903 (17)0.09047 (19)0.0196 (4)
C230.31293 (19)0.03064 (17)0.05098 (19)0.0201 (4)
C240.3623 (2)0.05123 (19)0.0790 (2)0.0243 (4)
H240.39400.01510.10550.029*
C250.3657 (2)0.1666 (2)0.1700 (2)0.0275 (4)
H250.40040.17990.25830.033*
C260.3180 (2)0.26238 (19)0.1302 (2)0.0281 (4)
H260.31720.34150.19160.034*
C270.2713 (2)0.24465 (18)0.0023 (2)0.0240 (4)
H270.24100.31190.02260.029*
C280.3029 (2)0.09482 (17)0.1464 (2)0.0212 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
K0.0236 (2)0.01461 (18)0.0195 (2)0.00072 (15)0.00917 (16)0.00773 (15)
S10.0179 (2)0.0111 (2)0.0223 (2)0.00063 (16)0.00674 (18)0.00661 (17)
S20.0223 (2)0.0113 (2)0.0166 (2)0.00094 (16)0.00695 (18)0.00533 (16)
S30.0165 (2)0.0181 (2)0.0269 (3)0.00257 (17)0.00043 (19)0.01389 (19)
S40.0238 (2)0.0162 (2)0.0217 (2)0.00477 (18)0.00022 (19)0.01007 (18)
O10.0246 (7)0.0139 (6)0.0254 (7)0.0003 (5)0.0072 (6)0.0112 (5)
O20.0186 (6)0.0169 (6)0.0212 (7)0.0016 (5)0.0065 (5)0.0104 (5)
O30.0248 (7)0.0149 (6)0.0165 (6)0.0021 (5)0.0063 (6)0.0068 (5)
O40.0392 (9)0.0120 (6)0.0212 (7)0.0032 (6)0.0102 (7)0.0058 (5)
O50.0239 (7)0.0180 (6)0.0305 (8)0.0013 (6)0.0049 (6)0.0148 (6)
O60.0183 (6)0.0157 (6)0.0236 (7)0.0018 (5)0.0049 (6)0.0111 (5)
O70.0394 (9)0.0165 (7)0.0240 (8)0.0050 (6)0.0025 (7)0.0086 (6)
O80.0331 (8)0.0183 (7)0.0275 (8)0.0024 (6)0.0093 (7)0.0125 (6)
C10.0210 (9)0.0098 (7)0.0126 (8)0.0003 (6)0.0047 (7)0.0035 (6)
C20.0185 (8)0.0140 (8)0.0144 (8)0.0004 (7)0.0046 (7)0.0064 (7)
C30.0180 (8)0.0149 (8)0.0171 (9)0.0009 (7)0.0045 (7)0.0067 (7)
C40.0208 (10)0.0187 (9)0.0338 (11)0.0018 (7)0.0044 (8)0.0157 (8)
C50.0188 (10)0.0246 (10)0.0410 (13)0.0030 (8)0.0038 (9)0.0192 (9)
C60.0184 (9)0.0237 (10)0.0316 (11)0.0032 (8)0.0023 (8)0.0114 (9)
C70.0225 (9)0.0145 (8)0.0233 (10)0.0014 (7)0.0054 (8)0.0078 (7)
C80.0157 (8)0.0148 (8)0.0154 (8)0.0003 (6)0.0044 (7)0.0057 (7)
C90.0152 (8)0.0145 (8)0.0158 (8)0.0008 (6)0.0049 (7)0.0056 (7)
C100.0185 (9)0.0179 (8)0.0164 (9)0.0034 (7)0.0034 (7)0.0037 (7)
C110.0211 (9)0.0268 (10)0.0142 (9)0.0014 (8)0.0040 (7)0.0064 (7)
C120.0234 (9)0.0273 (10)0.0215 (10)0.0064 (8)0.0097 (8)0.0157 (8)
C130.0213 (9)0.0178 (8)0.0222 (9)0.0018 (7)0.0075 (8)0.0109 (7)
C140.0164 (8)0.0126 (8)0.0182 (9)0.0009 (6)0.0046 (7)0.0062 (7)
C150.0220 (9)0.0125 (8)0.0147 (8)0.0006 (7)0.0056 (7)0.0050 (6)
C160.0197 (9)0.0140 (8)0.0149 (8)0.0007 (7)0.0054 (7)0.0054 (7)
C170.0175 (8)0.0167 (8)0.0157 (8)0.0025 (7)0.0034 (7)0.0062 (7)
C180.0203 (9)0.0175 (8)0.0224 (9)0.0001 (7)0.0043 (8)0.0112 (7)
C190.0170 (9)0.0250 (10)0.0250 (10)0.0032 (8)0.0043 (8)0.0139 (8)
C200.0175 (9)0.0264 (10)0.0303 (11)0.0014 (8)0.0073 (8)0.0130 (8)
C210.0225 (9)0.0188 (9)0.0256 (10)0.0018 (7)0.0081 (8)0.0105 (8)
C220.0168 (8)0.0176 (8)0.0232 (9)0.0028 (7)0.0037 (7)0.0102 (7)
C230.0197 (9)0.0175 (9)0.0235 (10)0.0011 (7)0.0064 (8)0.0102 (7)
C240.0266 (10)0.0251 (10)0.0265 (10)0.0004 (8)0.0112 (9)0.0143 (8)
C250.0314 (11)0.0294 (10)0.0245 (10)0.0015 (9)0.0125 (9)0.0110 (9)
C260.0333 (11)0.0213 (9)0.0319 (11)0.0007 (8)0.0184 (10)0.0063 (8)
C270.0240 (10)0.0176 (9)0.0314 (11)0.0005 (7)0.0112 (9)0.0105 (8)
C280.0228 (9)0.0169 (9)0.0262 (10)0.0030 (7)0.0079 (8)0.0113 (8)
Geometric parameters (Å, º) top
K—O7i2.6586 (16)C5—H50.9500
K—O3i2.6806 (14)C6—C71.381 (3)
K—O12.7436 (15)C6—H60.9500
K—O52.7960 (15)C7—H70.9500
K—O2ii2.8086 (14)C8—C131.399 (2)
K—O6ii3.0661 (15)C8—C91.415 (2)
K—S1ii3.1733 (7)C9—C101.396 (3)
K—S3ii3.5499 (8)C9—C141.477 (2)
S1—C31.7893 (19)C10—C111.382 (3)
S1—S22.0465 (7)C10—H100.9500
S1—Kii3.1733 (7)C11—C121.384 (3)
S2—C81.7899 (19)C11—H110.9500
S3—C171.7910 (19)C12—C131.381 (3)
S3—S42.0423 (7)C12—H120.9500
S3—Kii3.5499 (8)C13—H130.9500
S4—C221.794 (2)C15—C161.489 (2)
O1—C11.251 (2)C16—C211.399 (3)
O2—C11.273 (2)C16—C171.412 (2)
O2—Kii2.8086 (14)C17—C181.392 (3)
O3—C141.215 (2)C18—C191.387 (3)
O3—Kiii2.6806 (14)C18—H180.9500
O4—C141.328 (2)C19—C201.389 (3)
O4—H1O0.8400C19—H190.9500
O5—C151.234 (2)C20—C211.374 (3)
O6—C151.299 (2)C20—H200.9500
O6—Kii3.0661 (15)C21—H210.9500
O6—H2O0.8401C22—C271.396 (3)
O7—C281.216 (3)C22—C231.410 (3)
O7—Kiii2.6586 (16)C23—C241.397 (3)
O8—C281.326 (2)C23—C281.480 (3)
O8—H3O0.8400C24—C251.384 (3)
C1—C21.498 (2)C24—H240.9500
C2—C71.393 (3)C25—C261.385 (3)
C2—C31.402 (2)C25—H250.9500
C3—C41.399 (3)C26—C271.383 (3)
C4—C51.386 (3)C26—H260.9500
C4—H40.9500C27—H270.9500
C5—C61.389 (3)
O7i—K—O3i96.77 (5)C6—C5—H5119.8
O7i—K—O1129.86 (5)C7—C6—C5118.79 (19)
O3i—K—O171.45 (4)C7—C6—H6120.6
O7i—K—O571.64 (5)C5—C6—H6120.6
O3i—K—O5131.40 (5)C6—C7—C2121.89 (17)
O1—K—O580.67 (4)C6—C7—H7119.1
O7i—K—O2ii102.50 (5)C2—C7—H7119.1
O3i—K—O2ii156.62 (4)C13—C8—C9118.12 (17)
O1—K—O2ii104.90 (4)C13—C8—S2121.69 (14)
O5—K—O2ii68.35 (4)C9—C8—S2120.13 (14)
O7i—K—O6ii165.18 (5)C10—C9—C8119.83 (17)
O3i—K—O6ii91.66 (4)C10—C9—C14119.97 (16)
O1—K—O6ii64.50 (4)C8—C9—C14120.16 (16)
O5—K—O6ii111.36 (4)C11—C10—C9120.93 (18)
O2ii—K—O6ii66.83 (4)C11—C10—H10119.5
O7i—K—S1ii76.34 (4)C9—C10—H10119.5
O3i—K—S1ii119.10 (3)C10—C11—C12119.14 (18)
O1—K—S1ii152.42 (3)C10—C11—H11120.4
O5—K—S1ii104.08 (4)C12—C11—H11120.4
O2ii—K—S1ii54.55 (3)C13—C12—C11121.05 (18)
O6ii—K—S1ii88.92 (3)C13—C12—H12119.5
O7i—K—C1132.30 (5)C11—C12—H12119.5
O3i—K—C191.89 (4)C12—C13—C8120.76 (18)
O1—K—C120.67 (4)C12—C13—H13119.6
O5—K—C167.73 (4)C8—C13—H13119.6
O2ii—K—C184.91 (4)O3—C14—O4122.96 (17)
O6ii—K—C159.17 (4)O3—C14—C9122.95 (16)
S1ii—K—C1137.02 (4)O4—C14—C9114.07 (16)
O7i—K—S3ii126.93 (4)O5—C15—O6122.01 (17)
O3i—K—S3ii63.62 (3)O5—C15—C16121.54 (17)
O1—K—S3ii92.08 (3)O6—C15—C16116.45 (15)
O5—K—S3ii158.01 (3)C21—C16—C17119.09 (17)
O2ii—K—S3ii93.93 (3)C21—C16—C15116.14 (16)
O6ii—K—S3ii47.48 (3)C17—C16—C15124.77 (17)
S1ii—K—S3ii73.298 (18)C18—C17—C16118.50 (17)
C1—K—S3ii98.84 (4)C18—C17—S3120.19 (14)
C3—S1—S2106.32 (6)C16—C17—S3121.29 (14)
C3—S1—Kii117.10 (6)C19—C18—C17121.31 (17)
S2—S1—Kii117.18 (2)C19—C18—H18119.3
C8—S2—S1103.19 (6)C17—C18—H18119.3
C17—S3—S4105.25 (6)C18—C19—C20120.18 (18)
C17—S3—Kii122.79 (6)C18—C19—H19119.9
S4—S3—Kii115.73 (3)C20—C19—H19119.9
C22—S4—S3104.75 (7)C21—C20—C19119.20 (19)
C1—O1—K108.58 (11)C21—C20—H20120.4
C1—O2—Kii150.37 (12)C19—C20—H20120.4
C14—O3—Kiii129.98 (12)C20—C21—C16121.71 (18)
C14—O4—H1O106.2C20—C21—H21119.1
C15—O5—K128.86 (13)C16—C21—H21119.1
C15—O6—Kii143.84 (11)C27—C22—C23118.46 (18)
C15—O6—H2O109.1C27—C22—S4121.72 (15)
Kii—O6—H2O80.5 (18)C23—C22—S4119.78 (15)
C28—O7—Kiii138.62 (13)C24—C23—C22119.70 (18)
C28—O8—H3O108.8C24—C23—C28119.61 (17)
O1—C1—O2123.42 (17)C22—C23—C28120.65 (18)
O1—C1—C2118.14 (17)C25—C24—C23121.10 (19)
O2—C1—C2118.43 (15)C25—C24—H24119.5
O1—C1—K50.75 (9)C23—C24—H24119.5
O2—C1—K89.28 (10)C24—C25—C26118.9 (2)
C2—C1—K132.00 (11)C24—C25—H25120.5
C7—C2—C3119.20 (17)C26—C25—H25120.5
C7—C2—C1116.45 (16)C27—C26—C25121.0 (2)
C3—C2—C1124.35 (16)C27—C26—H26119.5
C4—C3—C2118.82 (17)C25—C26—H26119.5
C4—C3—S1121.17 (14)C26—C27—C22120.77 (19)
C2—C3—S1120.00 (14)C26—C27—H27119.6
C5—C4—C3120.82 (18)C22—C27—H27119.6
C5—C4—H4119.6O7—C28—O8123.05 (18)
C3—C4—H4119.6O7—C28—C23122.69 (18)
C4—C5—C6120.47 (19)O8—C28—C23114.24 (17)
C4—C5—H5119.8
C3—S1—S2—C899.20 (9)C5—C6—C7—C20.1 (3)
Kii—S1—S2—C8127.65 (6)C3—C2—C7—C60.1 (3)
C17—S3—S4—C2280.05 (9)C1—C2—C7—C6179.66 (18)
Kii—S3—S4—C22140.98 (7)S1—S2—C8—C1314.36 (17)
O7i—K—O1—C1105.72 (13)S1—S2—C8—C9162.90 (14)
O3i—K—O1—C1171.05 (13)C13—C8—C9—C104.5 (3)
O5—K—O1—C149.30 (12)S2—C8—C9—C10172.87 (14)
O2ii—K—O1—C115.19 (13)C13—C8—C9—C14173.11 (17)
O6ii—K—O1—C169.87 (12)S2—C8—C9—C149.5 (2)
S1ii—K—O1—C153.30 (16)C8—C9—C10—C111.9 (3)
S3ii—K—O1—C1109.82 (12)C14—C9—C10—C11175.66 (17)
O7i—K—O5—C15153.39 (17)C9—C10—C11—C121.7 (3)
O3i—K—O5—C15123.90 (16)C10—C11—C12—C132.8 (3)
O1—K—O5—C1568.98 (16)C11—C12—C13—C80.2 (3)
O2ii—K—O5—C1541.24 (16)C9—C8—C13—C123.5 (3)
O6ii—K—O5—C1511.17 (17)S2—C8—C13—C12173.84 (15)
S1ii—K—O5—C1583.26 (16)Kiii—O3—C14—O429.1 (3)
C1—K—O5—C1552.17 (16)Kiii—O3—C14—C9152.68 (13)
S3ii—K—O5—C153.0 (2)C10—C9—C14—O3179.17 (18)
K—O1—C1—O256.0 (2)C8—C9—C14—O31.6 (3)
K—O1—C1—C2122.87 (14)C10—C9—C14—O40.8 (2)
Kii—O2—C1—O1141.59 (18)C8—C9—C14—O4176.81 (17)
Kii—O2—C1—C237.3 (3)K—O5—C15—O630.2 (3)
Kii—O2—C1—K101.6 (2)K—O5—C15—C16149.79 (13)
O7i—K—C1—O192.45 (13)Kii—O6—C15—O596.3 (2)
O3i—K—C1—O18.48 (12)Kii—O6—C15—C1683.7 (2)
O5—K—C1—O1126.07 (13)O5—C15—C16—C214.0 (3)
O2ii—K—C1—O1165.27 (12)O6—C15—C16—C21176.03 (17)
O6ii—K—C1—O199.29 (13)O5—C15—C16—C17175.73 (18)
S1ii—K—C1—O1147.01 (11)O6—C15—C16—C174.2 (3)
S3ii—K—C1—O172.07 (12)C21—C16—C17—C180.1 (3)
O7i—K—C1—O2131.37 (10)C15—C16—C17—C18179.68 (17)
O3i—K—C1—O2127.70 (10)C21—C16—C17—S3178.20 (14)
O1—K—C1—O2136.18 (18)C15—C16—C17—S32.1 (3)
O5—K—C1—O297.75 (11)S4—S3—C17—C1811.76 (17)
O2ii—K—C1—O229.09 (12)Kii—S3—C17—C18147.07 (13)
O6ii—K—C1—O236.89 (9)S4—S3—C17—C16170.00 (14)
S1ii—K—C1—O210.83 (13)Kii—S3—C17—C1634.69 (18)
S3ii—K—C1—O264.11 (10)C16—C17—C18—C190.1 (3)
O7i—K—C1—C22.37 (18)S3—C17—C18—C19178.21 (16)
O3i—K—C1—C2103.30 (15)C17—C18—C19—C200.3 (3)
O1—K—C1—C294.8 (2)C18—C19—C20—C210.6 (3)
O5—K—C1—C231.25 (15)C19—C20—C21—C160.6 (3)
O2ii—K—C1—C299.91 (15)C17—C16—C21—C200.3 (3)
O6ii—K—C1—C2165.89 (17)C15—C16—C21—C20179.95 (18)
S1ii—K—C1—C2118.17 (15)S3—S4—C22—C273.69 (18)
S3ii—K—C1—C2166.89 (15)S3—S4—C22—C23173.96 (14)
O1—C1—C2—C719.6 (2)C27—C22—C23—C241.9 (3)
O2—C1—C2—C7159.39 (17)S4—C22—C23—C24175.88 (15)
K—C1—C2—C741.5 (2)C27—C22—C23—C28175.62 (18)
O1—C1—C2—C3160.18 (18)S4—C22—C23—C286.6 (3)
O2—C1—C2—C320.8 (3)C22—C23—C24—C251.3 (3)
K—C1—C2—C3138.76 (15)C28—C23—C24—C25176.20 (19)
C7—C2—C3—C40.6 (3)C23—C24—C25—C260.7 (3)
C1—C2—C3—C4179.18 (18)C24—C25—C26—C272.1 (3)
C7—C2—C3—S1179.68 (14)C25—C26—C27—C221.5 (3)
C1—C2—C3—S10.6 (3)C23—C22—C27—C260.5 (3)
S2—S1—C3—C40.94 (18)S4—C22—C27—C26177.21 (16)
Kii—S1—C3—C4132.26 (15)Kiii—O7—C28—O832.8 (3)
S2—S1—C3—C2178.79 (13)Kiii—O7—C28—C23145.73 (16)
Kii—S1—C3—C248.01 (17)C24—C23—C28—O7171.4 (2)
C2—C3—C4—C50.8 (3)C22—C23—C28—O76.1 (3)
S1—C3—C4—C5179.44 (17)C24—C23—C28—O87.2 (3)
C3—C4—C5—C60.6 (4)C22—C23—C28—O8175.31 (18)
C4—C5—C6—C70.1 (4)
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z+1; (iii) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1o···O1iii0.841.802.631 (2)169
O6—H2o···O2ii0.841.682.515 (2)177
O8—H3o···O5iii0.841.882.704 (2)167
Symmetry codes: (ii) x, y+1, z+1; (iii) x, y1, z.

Experimental details

Crystal data
Chemical formulaK+·C14H9O4S2·C14H10O4S2
Mr650.81
Crystal system, space groupTriclinic, 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)
V3)1383.5 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.55
Crystal size (mm)0.50 × 0.25 × 0.20
Data collection
DiffractometerRigaku AFC12K/SATURN724
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.840, 1
No. of measured, independent and
observed [I > 2σ(I)] reflections
10251, 6302, 5938
Rint0.030
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.102, 1.07
No. of reflections6302
No. of parameters379
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O4—H1o···O1i0.841.802.631 (2)169
O6—H2o···O2ii0.841.682.515 (2)177
O8—H3o···O5i0.841.882.704 (2)167
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z+1.
 

References

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

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