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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3202.
Published online 2009 November 25. doi:  10.1107/S1600536809049824
PMCID: PMC2971994

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

Abstract

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 [triangle]). For related studies on co-crystal formation with 2,2′-disulfanediyl­dibenzoic acid, see: Broker & Tiekink (2007 [triangle]); Broker et al. (2008 [triangle]).

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Object name is e-65-o3202-scheme1.jpg

Experimental

Crystal data

  • K+·C14H9O4S2 ·C14H10O4S2
  • M r = 650.81
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3202-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

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.

Crystal data

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

Rigaku AFC12K/SATURN724 diffractometer6302 independent reflections
Radiation source: fine-focus sealed tube5938 reflections with I > 2σ(I)
graphiteRint = 0.030
ω scansθmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −14→14
Tmin = 0.840, Tmax = 1k = −12→15
10251 measured reflectionsl = −16→16

Refinement

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 = 1.07w = 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

Special details

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)

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)
H1O0.1205−0.45010.74840.037*
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)
H3O0.3404−0.24650.15470.040*
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)
H100.0549−0.40391.00220.023*
C110.0616 (2)−0.26811 (18)1.05393 (19)0.0226 (4)
H110.0371−0.31631.14250.027*
C120.0886 (2)−0.14551 (18)1.00653 (19)0.0224 (4)
H120.0863−0.11051.06260.027*
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)
H240.3940−0.0151−0.10550.029*
C250.3657 (2)0.1666 (2)−0.1700 (2)0.0275 (4)
H250.40040.1799−0.25830.033*
C260.3180 (2)0.26238 (19)−0.1302 (2)0.0281 (4)
H260.31720.3415−0.19160.034*
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)

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, °)

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—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—C6179.66 (18)
Kii—S3—S4—C22140.98 (7)S1—S2—C8—C13−14.36 (17)
O7i—K—O1—C1−105.72 (13)S1—S2—C8—C9162.90 (14)
O3i—K—O1—C1171.05 (13)C13—C8—C9—C104.5 (3)
O5—K—O1—C1−49.30 (12)S2—C8—C9—C10−172.87 (14)
O2ii—K—O1—C115.19 (13)C13—C8—C9—C14−173.11 (17)
O6ii—K—O1—C169.87 (12)S2—C8—C9—C149.5 (2)
S1ii—K—O1—C153.30 (16)C8—C9—C10—C11−1.9 (3)
S3ii—K—O1—C1109.82 (12)C14—C9—C10—C11175.66 (17)
O7i—K—O5—C15−153.39 (17)C9—C10—C11—C12−1.7 (3)
O3i—K—O5—C15123.90 (16)C10—C11—C12—C132.8 (3)
O1—K—O5—C1568.98 (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—C1511.17 (17)S2—C8—C13—C12173.84 (15)
S1ii—K—O5—C15−83.26 (16)Kiii—O3—C14—O429.1 (3)
C1—K—O5—C1552.17 (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—C2122.87 (14)C10—C9—C14—O4−0.8 (2)
Kii—O2—C1—O1141.59 (18)C8—C9—C14—O4176.81 (17)
Kii—O2—C1—C2−37.3 (3)K—O5—C15—O630.2 (3)
Kii—O2—C1—K101.6 (2)K—O5—C15—C16−149.79 (13)
O7i—K—C1—O192.45 (13)Kii—O6—C15—O5−96.3 (2)
O3i—K—C1—O1−8.48 (12)Kii—O6—C15—C1683.7 (2)
O5—K—C1—O1126.07 (13)O5—C15—C16—C21−4.0 (3)
O2ii—K—C1—O1−165.27 (12)O6—C15—C16—C21176.03 (17)
O6ii—K—C1—O1−99.29 (13)O5—C15—C16—C17175.73 (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—C180.1 (3)
O7i—K—C1—O2−131.37 (10)C15—C16—C17—C18−179.68 (17)
O3i—K—C1—O2127.70 (10)C21—C16—C17—S3−178.20 (14)
O1—K—C1—O2136.18 (18)C15—C16—C17—S32.1 (3)
O5—K—C1—O2−97.75 (11)S4—S3—C17—C1811.76 (17)
O2ii—K—C1—O2−29.09 (12)Kii—S3—C17—C18147.07 (13)
O6ii—K—C1—O236.89 (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—O264.11 (10)C16—C17—C18—C19−0.1 (3)
O7i—K—C1—C2−2.37 (18)S3—C17—C18—C19178.21 (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—C210.6 (3)
O5—K—C1—C231.25 (15)C19—C20—C21—C16−0.6 (3)
O2ii—K—C1—C299.91 (15)C17—C16—C21—C200.3 (3)
O6ii—K—C1—C2165.89 (17)C15—C16—C21—C20−179.95 (18)
S1ii—K—C1—C2118.17 (15)S3—S4—C22—C27−3.69 (18)
S3ii—K—C1—C2−166.89 (15)S3—S4—C22—C23173.96 (14)
O1—C1—C2—C7−19.6 (2)C27—C22—C23—C241.9 (3)
O2—C1—C2—C7159.39 (17)S4—C22—C23—C24−175.88 (15)
K—C1—C2—C741.5 (2)C27—C22—C23—C28−175.62 (18)
O1—C1—C2—C3160.18 (18)S4—C22—C23—C286.6 (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—C25176.20 (19)
C7—C2—C3—C40.6 (3)C23—C24—C25—C26−0.7 (3)
C1—C2—C3—C4−179.18 (18)C24—C25—C26—C272.1 (3)
C7—C2—C3—S1−179.68 (14)C25—C26—C27—C22−1.5 (3)
C1—C2—C3—S10.6 (3)C23—C22—C27—C26−0.5 (3)
S2—S1—C3—C40.94 (18)S4—C22—C27—C26177.21 (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—C23145.73 (16)
Kii—S1—C3—C248.01 (17)C24—C23—C28—O7−171.4 (2)
C2—C3—C4—C5−0.8 (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—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, °)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2606).

References

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  • Broker, G. A., Bettens, R. P. A. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 879–887.
  • Broker, G. A. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 1096–1109.
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  • Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF. In preparation.
  • Zukerman-Schpector, J. & Tiekink, E. R. T. (2008). Z. Kristallogr. 223, 233–234.

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