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Acta Cryst. (2007). E63, m3056-m3057    [ doi:10.1107/S1600536807056930 ]

Dipotassium biphenyl-4,4'-disulfonate dihydrate: a coordination polymer

G. Smith, U. D. Wermuth and P. C. Healy

Abstract top

The polymeric structure of the title compound, poly[[diaquabis([mu]-biphenyl-4,4'-disulfonato)tetrapotassium(I)] dihydrate], {[K2(C12H8O6S2)(H2O)]·H2O}n, is based on an asymmetric unit comprising three independent and different potassium centres, one six-coordinate [K-O = 2.657 (3)-2.866 (5) Å], one seven-coordinate [K-O = 2.703 (3)-3.040 (4) Å], and the third ten-coordinate [K-O = 2.751 (3)-3.079 (4) Å], with two of these lying on crystallographic mirror planes. The four half-occupancy water molecules also lie on the mirror planes with two coordinated (one monodentate, the other bidentate bridging) and two as molecules of solvation. The interlinked coordination polyhedra form chains which are joined laterally through the biphenyl residues as well as through head-to-tail water hydrogen-bonding interactions, giving a two-dimensional structure.

Comment top

Compounds of 4,4'-biphenyldisulfonic acid (BPDS) are not numerous in the crystallographic literature. The guanidinium salts have been used for the generation of 2-D structures for the formation of crystalline clathrates with aromatic hydrocarbons (Swift et al., 1998; Pivovar et al., 2002). The bis(alaninium) salt is also known (Liao et al., 2001). With coordination compounds, BDPDS is generally found as a dianionic counter ion (Cai et al., 2001; Usuki et al., 2002). We obtained X-ray diffraction quality crystals of the hydrated dipotassium salt of BPDS as an intermediate in the synthesis of BPDS, when recrystallized from water. The structure of this compound, K22+·C12H8O6S22−·2H2O (I) is reported here.

The structure of (I) is based on an asymmetric unit comprising three independent and different potassium centres, one six-coordinate (K2) [K–O range, 2.657 (3)–2.866 (5) Å], one seven- coordinate (K1) [K–O range, 2.703 (3)–3.040 (4) Å] and the third ten-coordinate (K3) [K–O range, 2.751 (3)–3.079 (4) Å], with two of these (K2 and K3) lying on crystallographic mirror planes (Fig. 1). The four half-occupancy water molecules also lie on the mirror planes with two coordinated [one monodentate (O1W on K2), and one bidentate (O2W, bridging K2 and K3)], and the other two (OW3, OW4) as molecules of solvation. The structure has pseudo 2/m symmetry, the 2-fold rotational symmetry along the b axis being upset largely by the differing roles of the water molecules in the structure. This was also consistent with the failure to obtain a solution of the structure in the space group C2/m.

The interlinked potassium coordination polyhedra form chains which extend down the b axix and are linked laterally across the c cell direction through the biphenyl residues of the BPDS ligands, giving a 2-D structure (Fig. 2). This is somewhat analogous to the 2-D but hydrogen-bonded guanidinium-BPDS open framework structures (Swift et al., 1998; Pivovar et al., 2002) which accommodate interstitial inert aromatic molecules. With (I), the water molecules are similarly accommodated in the interstitial spaces along the crystallographic mirror planes in linear head-to-tail interactions (Table 1) and also link the coordination polymer chains. In addition, the coordinated water molecules give lateral O–H···Osulfonate interactions within the polymer chains.

Within the BPDS anion, the two phenyl rings (A and B) are close to co-planar [torsion angle C2A–C1A–C1B–C6B, −178.3 (5) °], which is similar to that found in the alaninium salt where the two residues are inversion related (Liao et al., 2001).

Related literature top

For other 4,4'-biphenyldisulfonate crystal structures, see: Swift et al. (1998); Liao et al. (2001); Cai et al. (2001); Usuki et al. (2002). For related literature, see: Pivovar et al. (2002). For synthesis, see: Feldmann (1931).

Experimental top

The title compound was obtained as colourless crystals from the room temperature evaporation of an aqueous solution of dipotassium 4,4-biphenyldisulfonate, an intermediate product in the synthesis of 4,4'-biphenyldisulfonic acid by the sulfonation of biphenyl using the procedure of Feldmann (1931).

Refinement top

Hydrogen atoms on the water molecules were located by difference methods but their positional and isotropic displacement parameters were fixed as located and Uiso(H) = 1.2Ueq(O), respectively; see Table 1 for distances. The aromatic H atoms were included in the refinement in their calculated positions (C–H = 0.94–0.95 Å) using a riding model approximation, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: MSC/AFC Diffractmeter Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractmeter Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. Molecular configuration and atom naming scheme for the BPDS ligand, the three independent potassium coordination polyhedra and the water molecules in the asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen-bonding interactions associated with the water molecules. The two potassium ions (K2, K3) and the four water molecules (O1W–O4W) lie on a crystallographic mirror plane. Symmetry codes: (i) x − 1, y, z; (ii) x − 1, y, z + 1; (iii) x, y, z + 1; (iv) x − 1/2, −y + 1/2, z; (v) x − 1/2, −y + 1/2, z + 1; (vi) x − 1, −y, z + 1; (vii) x, −y, z + 1; (viii) x + 1, y, z; (ix) x, −y, z.
[Figure 2] Fig. 2. The 2-D hydrogen-bonded structure of (I) viewed down the a axis, showing K–Osulfonate coordination-polymer chains with the biphenyl step linkages, together with the water mediated hydrogen-bonding associations lying on the mirror planes at y = 0, 1/2.
dipotassium biphenyl-4,4'-disulfonate dihydrate top
Crystal data top
2K+·C12H8O6S22–·2H2OF000 = 872
Mr = 426.56Dx = 1.708 Mg m−3
Monoclinic, CmMo Kα radiation
λ = 0.71073 Å
Hall symbol: C -2yCell parameters from 25 reflections
a = 5.8316 (10) Åθ = 12.9–17.1º
b = 19.691 (7) ŵ = 0.86 mm−1
c = 14.623 (2) ÅT = 297 (2) K
β = 98.953 (13)ºBlock, colourless
V = 1658.7 (7) Å30.32 × 0.25 × 0.20 mm
Z = 4
Data collection top
Rigaku AFC 7R
diffractometer		Rint = 0.016
Radiation source: rotating anodeθmax = 27.5º
Monochromator: graphiteθmin = 2.5º
T = 297(2) Kh = −3→7
ω–2θ scansk = 0→25
Absorption correction: ψ scan
(TEXSAN for Windows; Molecular Structure Corporation, 1999)		l = −18→18
Tmin = 0.774, Tmax = 0.8493 standard reflections
2295 measured reflections every 150 min
2295 independent reflections intensity decay: 0.6%
2196 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters not refined
R[F2 > 2σ(F2)] = 0.031  w = 1/[σ2(Fo2) + (0.1P)2 + 15.7726P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.083(Δ/σ)max = 0.002
S = 0.88Δρmax = 0.40 e Å−3
2295 reflectionsΔρmin = −0.39 e Å−3
227 parametersExtinction correction: none
2 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (8)
Secondary atom site location: difference Fourier map
Crystal data top
2K+·C12H8O6S22–·2H2OV = 1658.7 (7) Å3
Mr = 426.56Z = 4
Monoclinic, CmMo Kα
a = 5.8316 (10) ŵ = 0.86 mm−1
b = 19.691 (7) ÅT = 297 (2) K
c = 14.623 (2) Å0.32 × 0.25 × 0.20 mm
β = 98.953 (13)º
Data collection top
Rigaku AFC 7R
diffractometer		2196 reflections with I > 2σ(I)
Absorption correction: ψ scan
(TEXSAN for Windows; Molecular Structure Corporation, 1999)		Rint = 0.016
Tmin = 0.774, Tmax = 0.8493 standard reflections
2295 measured reflections every 150 min
2295 independent reflections intensity decay: 0.6%
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters not refined
wR(F2) = 0.083  w = 1/[σ2(Fo2) + (0.1P)2 + 15.7726P]
where P = (Fo2 + 2Fc2)/3
S = 0.88Δρmax = 0.40 e Å−3
2295 reflectionsΔρmin = −0.39 e Å−3
227 parametersAbsolute structure: Flack (1983)
2 restraintsFlack parameter: 0.02 (8)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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
K10.27341 (18)0.18494 (4)0.50427 (7)0.0306 (2)
K20.3806 (2)0.000000.66340 (8)0.0322 (3)
K30.8140 (2)0.000000.48912 (8)0.0331 (3)
S4A0.85074 (12)0.13645 (4)−0.35496 (5)0.0216 (2)
S4B0.67991 (14)0.14568 (5)0.35851 (6)0.0255 (2)
O1W0.4854 (11)0.000000.8501 (4)0.080 (3)
O2W0.2800 (7)0.000000.4652 (3)0.0354 (12)
O41A0.8714 (6)0.20502 (15)−0.3888 (2)0.0431 (9)
O41B0.9000 (5)0.12170 (17)0.40854 (18)0.0370 (9)
O42A0.6357 (5)0.10358 (17)−0.39554 (19)0.0374 (9)
O42B0.4950 (6)0.09558 (17)0.3603 (2)0.0404 (10)
O43A1.0527 (5)0.09479 (17)−0.3630 (2)0.0403 (10)
O43B0.6088 (6)0.21186 (17)0.3865 (2)0.0389 (9)
C1A0.7952 (7)0.15078 (19)−0.0464 (3)0.0274 (10)
C1B0.7699 (7)0.1525 (2)0.0539 (3)0.0285 (10)
C2A0.6400 (8)0.1846 (3)−0.1132 (3)0.0459 (15)
C2B0.5868 (9)0.1849 (2)0.0848 (3)0.0427 (14)
C3A0.6591 (9)0.1809 (2)−0.2069 (3)0.0424 (15)
C3B0.5603 (8)0.1853 (2)0.1778 (3)0.0429 (15)
C4A0.8342 (7)0.14383 (19)−0.2346 (2)0.0253 (10)
C4B0.7182 (7)0.1511 (2)0.2407 (3)0.0273 (10)
C5A0.9927 (8)0.1114 (3)−0.1700 (3)0.0497 (16)
C5B0.9036 (10)0.1196 (4)0.2123 (3)0.065 (2)
C6A0.9716 (9)0.1150 (3)−0.0765 (3)0.0533 (18)
C6B0.9281 (9)0.1203 (4)0.1193 (3)0.066 (2)
O3W0.3491 (11)0.000000.2133 (3)0.0608 (19)
O4W0.4275 (14)0.000000.0351 (5)0.083 (2)
H2A0.518700.20980−0.093000.0550*
H2B0.477800.207400.040900.0510*
H2W0.348000.039000.440000.0420*
H3A0.551600.20360−0.251800.0500*
H3B0.433800.207700.197900.0510*
H5A1.114000.08620−0.190200.0600*
H5B1.012600.097100.256200.0780*
H6A1.079100.09230−0.031600.0640*
H6B1.054600.097900.099200.0790*
H11W0.356000.000000.884000.0960*
H12W0.614000.000000.884000.0960*
H3W0.397000.038500.252000.0730*
H41W0.402000.000000.094000.0970*
H42W0.579400.000000.037500.0970*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
K10.0334 (4)0.0286 (4)0.0307 (3)−0.0007 (4)0.0082 (3)0.0001 (4)
K20.0286 (6)0.0346 (6)0.0344 (6)0.00000.0083 (5)0.0000
K30.0357 (6)0.0317 (5)0.0325 (6)0.00000.0076 (5)0.0000
S4A0.0243 (4)0.0239 (4)0.0174 (4)0.0011 (3)0.0058 (3)0.0000 (3)
S4B0.0310 (4)0.0297 (4)0.0166 (4)−0.0042 (4)0.0062 (3)−0.0006 (3)
O1W0.073 (4)0.116 (6)0.045 (3)0.0000−0.005 (3)0.0000
O2W0.038 (2)0.036 (2)0.035 (2)0.00000.0147 (17)0.0000
O41A0.076 (2)0.0276 (14)0.0285 (14)−0.0031 (16)0.0174 (15)0.0044 (11)
O41B0.0383 (16)0.0489 (17)0.0230 (13)0.0000 (14)0.0020 (11)0.0051 (12)
O42A0.0328 (14)0.0533 (18)0.0267 (14)−0.0133 (14)0.0063 (11)−0.0078 (12)
O42B0.0453 (17)0.0468 (19)0.0302 (14)−0.0183 (15)0.0095 (13)0.0004 (13)
O43A0.0370 (16)0.057 (2)0.0279 (14)0.0217 (15)0.0085 (12)0.0012 (13)
O43B0.0518 (17)0.0391 (16)0.0277 (14)0.0023 (14)0.0120 (13)−0.0056 (12)
C1A0.0342 (19)0.0320 (18)0.0168 (15)0.0031 (16)0.0068 (14)0.0009 (13)
C1B0.0317 (19)0.0359 (19)0.0181 (16)0.0004 (16)0.0041 (14)−0.0003 (14)
C2A0.051 (3)0.069 (3)0.0196 (17)0.030 (2)0.0114 (18)0.0024 (18)
C2B0.049 (2)0.058 (3)0.0222 (19)0.024 (2)0.0086 (17)0.0073 (19)
C3A0.049 (3)0.059 (3)0.0196 (18)0.025 (2)0.0071 (17)0.0072 (17)
C3B0.050 (3)0.056 (3)0.0252 (19)0.025 (2)0.0140 (18)0.0019 (17)
C4A0.0306 (18)0.0305 (17)0.0154 (15)−0.0001 (15)0.0057 (14)−0.0018 (13)
C4B0.0318 (19)0.0332 (19)0.0170 (16)−0.0034 (15)0.0041 (14)−0.0016 (13)
C5A0.044 (2)0.084 (4)0.0220 (18)0.036 (3)0.0079 (17)0.001 (2)
C5B0.061 (3)0.116 (5)0.0188 (19)0.048 (3)0.012 (2)0.016 (2)
C6A0.052 (3)0.085 (4)0.0229 (18)0.037 (3)0.0059 (18)0.006 (2)
C6B0.054 (3)0.122 (5)0.023 (2)0.053 (3)0.014 (2)0.016 (3)
O3W0.080 (4)0.057 (3)0.040 (3)0.0000−0.008 (3)0.0000
O4W0.091 (5)0.104 (6)0.055 (4)0.00000.003 (4)0.0000
Geometric parameters (Å, °) top
K1—O43B2.850 (4)S4B—C4B1.775 (4)
K1—O41Bi2.703 (3)O1W—H12W0.8300
K1—O41Aii3.040 (4)O1W—H11W0.9700
K1—O43Aii3.058 (3)O2W—H2Wix0.9600
K1—O42Aiii2.866 (3)O2W—H2W0.9600
K1—O43Biv2.739 (3)O3W—H3W0.9600
K1—O41Av2.681 (3)O3W—H3Wix0.9600
K2—O1W2.703 (6)O4W—H41W0.9000
K2—O2W2.866 (5)O4W—H42W0.8800
K2—O43Aii2.657 (3)C1A—C6A1.375 (7)
K2—O42Aiii2.741 (3)C1A—C2A1.393 (6)
K2—O43Avi2.657 (3)C1A—C1B1.497 (6)
K2—O42Avii2.741 (3)C1B—C2B1.379 (6)
K3—O2W3.079 (4)C1B—C6B1.376 (7)
K3—O41B2.751 (3)C2A—C3A1.394 (6)
K3—O42B3.076 (4)C2B—C3B1.392 (6)
K3—O42Aiii2.938 (3)C3A—C4A1.367 (6)
K3—O43Aiii3.027 (3)C3B—C4B1.373 (6)
K3—O2Wviii2.793 (4)C4A—C5A1.372 (6)
K3—O41Bix2.751 (3)C4B—C5B1.366 (7)
K3—O42Bix3.076 (4)C5A—C6A1.394 (6)
K3—O42Avii2.938 (3)C5B—C6B1.389 (6)
K3—O43Avii3.027 (3)C2A—H2A0.9500
S4A—O41A1.450 (3)C2B—H2B0.9400
S4A—O42A1.453 (3)C3A—H3A0.9500
S4A—O43A1.455 (3)C3B—H3B0.9400
S4A—C4A1.784 (3)C5A—H5A0.9500
S4B—O41B1.454 (3)C5B—H5B0.9400
S4B—O42B1.465 (4)C6A—H6A0.9500
S4B—O43B1.446 (4)C6B—H6B0.9400
O41Bi—K1—O43B110.25 (9)O41Bix—K3—O42Bix48.53 (9)
O41Aii—K1—O43B160.66 (9)O41Bix—K3—O42Avii75.26 (9)
O43Aii—K1—O43B152.59 (10)O41Bix—K3—O43Avii71.01 (8)
O42Aiii—K1—O43B83.81 (9)O42Avii—K3—O42Bix72.09 (8)
O43B—K1—O43Biv71.84 (10)O42Bix—K3—O43Avii103.14 (9)
O41Av—K1—O43B95.63 (10)O42Avii—K3—O43Avii47.64 (8)
O41Aii—K1—O41Bi72.70 (9)O41A—S4A—O42A112.82 (19)
O41Bi—K1—O43Aii71.13 (9)O41A—S4A—O43A112.72 (19)
O41Bi—K1—O42Aiii118.54 (10)O41A—S4A—C4A106.33 (17)
O41Bi—K1—O43Biv80.84 (10)O42A—S4A—O43A111.95 (18)
O41Av—K1—O41Bi139.11 (11)O42A—S4A—C4A105.28 (17)
O41Aii—K1—O43Aii46.73 (8)O43A—S4A—C4A107.12 (18)
O41Aii—K1—O42Aiii112.09 (9)K3—S4B—O41B49.33 (13)
O41Aii—K1—O43Biv90.23 (10)K3—S4B—O42B62.39 (13)
O41Aii—K1—O41Av72.92 (10)K3—S4B—O43B129.77 (13)
O42Aiii—K1—O43Aii72.58 (9)K3—S4B—C4B122.20 (14)
O43Aii—K1—O43Biv133.53 (10)O41B—S4B—O42B111.53 (19)
O41Av—K1—O43Aii99.88 (9)O41B—S4B—O43B114.83 (19)
O42Aiii—K1—O43Biv153.45 (10)O41B—S4B—C4B105.87 (18)
O41Av—K1—O42Aiii94.61 (10)O42B—S4B—O43B111.0 (2)
O41Av—K1—O43Biv77.83 (9)O42B—S4B—C4B105.19 (18)
O1W—K2—O2W178.76 (17)O43B—S4B—C4B107.79 (18)
O1W—K2—O43Aii101.02 (12)K2—O2W—K380.85 (11)
O1W—K2—O42Aiii105.61 (11)K2—O2W—K3i85.61 (12)
O1W—K2—O43Avi101.02 (12)K3—O2W—K3i166.45 (17)
O1W—K2—O42Avii105.61 (11)K1x—O41A—S4A99.57 (16)
O2W—K2—O43Aii79.84 (9)K1xi—O41A—S4A158.5 (2)
O2W—K2—O42Aiii73.61 (8)K1x—O41A—K1xi85.21 (9)
O2W—K2—O43Avi79.84 (9)K3—O41B—S4B107.04 (16)
O2W—K2—O42Avii73.61 (8)K1viii—O41B—K3111.44 (10)
O42Aiii—K2—O43Aii81.09 (9)K1viii—O41B—S4B133.48 (19)
O43Aii—K2—O43Avi89.26 (10)K1xii—O42A—S4A118.71 (18)
O42Avii—K2—O43Aii152.93 (10)K2xii—O42A—S4A132.77 (17)
O42Aiii—K2—O43Avi152.93 (10)K3xii—O42A—S4A100.58 (15)
O42Aiii—K2—O42Avii96.15 (10)K1xii—O42A—K2xii100.58 (10)
O42Avii—K2—O43Avi81.09 (9)K1xii—O42A—K3xii113.15 (10)
S4B—K3—O2W78.47 (5)K2xii—O42A—K3xii85.52 (10)
S4B—K3—O41B23.63 (6)K3—O42B—S4B92.65 (15)
S4B—K3—O42B24.96 (7)K3xii—O43A—S4A96.74 (14)
S4B—K3—O42Aiii70.87 (6)K1x—O43A—S4A98.62 (15)
S4B—K3—O43Aiii85.56 (6)K2x—O43A—S4A163.26 (19)
S4B—K3—O2Wviii94.10 (6)K1x—O43A—K3xii95.55 (9)
S4B—K3—S4Bix111.64 (4)K2x—O43A—K3xii84.90 (9)
S4B—K3—O41Bix121.69 (7)K1x—O43A—K2x97.79 (9)
S4B—K3—O42Bix96.07 (7)K1—O43B—S4B104.92 (17)
S4B—K3—O42Avii145.18 (7)K1—O43B—K1xiii87.96 (9)
S4B—K3—O43Avii160.55 (7)K1xiii—O43B—S4B139.4 (2)
O2W—K3—O41B101.53 (8)H11W—O1W—H12W113.00
O2W—K3—O42B54.96 (9)K2—O1W—H11W117.00
O2W—K3—O42Aiii67.86 (8)K2—O1W—H12W130.00
O2W—K3—O43Aiii115.20 (9)K2—O2W—H2W111.00
O2W—K3—O2Wviii166.45 (13)K3—O2W—H2Wix65.00
S4Bix—K3—O2W78.47 (5)K2—O2W—H2Wix111.00
O2W—K3—O41Bix101.53 (8)K3—O2W—H2W65.00
O2W—K3—O42Bix54.96 (9)K3i—O2W—H2Wix121.00
O2W—K3—O42Avii67.86 (8)K3i—O2W—H2W121.00
O2W—K3—O43Avii115.20 (9)H2W—O2W—H2Wix106.00
O41B—K3—O42B48.53 (9)H3W—O3W—H3Wix104.00
O41B—K3—O42Aiii75.26 (9)H41W—O4W—H42W106.00
O41B—K3—O43Aiii71.01 (8)C2A—C1A—C6A117.2 (4)
O2Wviii—K3—O41B72.58 (8)C1B—C1A—C6A121.2 (4)
S4Bix—K3—O41B121.69 (7)C1B—C1A—C2A121.6 (4)
O41B—K3—O41Bix121.19 (10)C1A—C1B—C6B120.9 (4)
O41B—K3—O42Bix113.82 (9)C1A—C1B—C2B122.1 (4)
O41B—K3—O42Avii162.77 (10)C2B—C1B—C6B117.1 (4)
O41B—K3—O43Avii138.51 (9)C1A—C2A—C3A121.4 (4)
O42Aiii—K3—O42B72.09 (8)C1B—C2B—C3B122.1 (4)
O42B—K3—O43Aiii103.14 (9)C2A—C3A—C4A119.8 (4)
O2Wviii—K3—O42B115.52 (10)C2B—C3B—C4B119.1 (4)
S4Bix—K3—O42B96.07 (7)S4A—C4A—C3A119.6 (3)
O41Bix—K3—O42B113.82 (9)S4A—C4A—C5A120.5 (3)
O42B—K3—O42Bix75.45 (9)C3A—C4A—C5A119.9 (3)
O42Avii—K3—O42B122.82 (10)S4B—C4B—C3B120.5 (3)
O42B—K3—O43Avii169.11 (9)S4B—C4B—C5B119.5 (3)
O42Aiii—K3—O43Aiii47.64 (8)C3B—C4B—C5B120.0 (4)
O2Wviii—K3—O42Aiii120.66 (8)C4A—C5A—C6A119.9 (4)
S4Bix—K3—O42Aiii145.18 (7)C4B—C5B—C6B120.0 (5)
O41Bix—K3—O42Aiii162.77 (10)C1A—C6A—C5A121.7 (5)
O42Aiii—K3—O42Bix122.82 (10)C1B—C6B—C5B121.7 (5)
O42Aiii—K3—O42Avii87.93 (9)C1A—C2A—H2A118.00
O42Aiii—K3—O43Avii100.51 (9)C3A—C2A—H2A121.00
O2Wviii—K3—O43Aiii75.00 (9)C1B—C2B—H2B118.00
S4Bix—K3—O43Aiii160.55 (7)C3B—C2B—H2B120.00
O41Bix—K3—O43Aiii138.51 (9)C4A—C3A—H3A119.00
O42Bix—K3—O43Aiii169.11 (9)C2A—C3A—H3A121.00
O42Avii—K3—O43Aiii100.51 (9)C2B—C3B—H3B121.00
O43Aiii—K3—O43Avii76.15 (9)C4B—C3B—H3B120.00
S4Bix—K3—O2Wviii94.10 (6)C4A—C5A—H5A119.00
O2Wviii—K3—O41Bix72.58 (8)C6A—C5A—H5A121.00
O2Wviii—K3—O42Bix115.52 (10)C6B—C5B—H5B121.00
O2Wviii—K3—O42Avii120.66 (8)C4B—C5B—H5B119.00
O2Wviii—K3—O43Avii75.00 (9)C1A—C6A—H6A118.00
S4Bix—K3—O41Bix23.63 (6)C5A—C6A—H6A120.00
S4Bix—K3—O42Bix24.96 (7)C5B—C6B—H6B120.00
S4Bix—K3—O42Avii70.87 (6)C1B—C6B—H6B118.00
S4Bix—K3—O43Avii85.56 (6)
O41Bi—K1—O43B—S4B−63.28 (18)S4B—K3—O42Aiii—K136.28 (8)
O41Bi—K1—O43B—K1xiii155.80 (9)S4B—K3—O42Aiii—K2135.88 (8)
O43Aii—K1—O43B—S4B24.6 (3)O2W—K3—O42Aiii—K1−48.71 (11)
O43Aii—K1—O43B—K1xiii−116.35 (19)O41B—K3—O42Aiii—K160.57 (11)
O42Aiii—K1—O43B—S4B54.89 (16)O41B—K3—O42Aiii—K2160.18 (10)
O42Aiii—K1—O43B—K1xiii−86.03 (10)O42B—K3—O42Aiii—K19.96 (11)
O43Biv—K1—O43B—S4B−135.85 (18)O42B—K3—O42Aiii—K2109.57 (10)
O43Biv—K1—O43B—K1xiii83.23 (10)S4B—K3—O42Avii—K2−35.22 (15)
O41Av—K1—O43B—S4B148.94 (16)O42B—K3—O42Avii—K2−51.07 (12)
O41Av—K1—O43B—K1xiii8.02 (10)O42A—S4A—O41A—K1x−112.87 (16)
O43B—K1—O41Bi—S4Bi−92.7 (2)O42A—S4A—O41A—K1xi−11.5 (6)
O43B—K1—O43Aii—K210.8 (2)O43A—S4A—O41A—K1x15.15 (19)
O43B—K1—O43Aii—S4Aii−172.48 (16)O43A—S4A—O41A—K1xi116.5 (5)
O43B—K1—O42Aiii—K2−145.49 (11)C4A—S4A—O41A—K1x132.23 (15)
O43B—K1—O42Aiii—K3−55.87 (11)C4A—S4A—O41A—K1xi−126.4 (5)
O43B—K1—O42Aiii—S4Aiii61.65 (17)O41A—S4A—O42A—K1xii−13.0 (2)
O43B—K1—O43Biv—K1iv−165.58 (11)O41A—S4A—O42A—K2xii−155.4 (2)
O43B—K1—O43Biv—S4Biv−54.9 (3)O41A—S4A—O42A—K3xii110.94 (17)
O43B—K1—O41Av—S4Av96.8 (5)O43A—S4A—O42A—K1xii−141.42 (17)
O43B—K1—O41Av—K1xiii−7.24 (9)O43A—S4A—O42A—K2xii76.2 (3)
O1W—K2—O43Aii—K1125.43 (12)O43A—S4A—O42A—K3xii−17.47 (19)
O2W—K2—O43Aii—K1−53.67 (9)C4A—S4A—O42A—K1xii102.53 (18)
O1W—K2—O42Aiii—K1−121.86 (13)C4A—S4A—O42A—K2xii−39.8 (3)
O2W—K2—O42Aiii—K159.14 (10)C4A—S4A—O42A—K3xii−133.52 (14)
O2W—K3—S4B—O41B167.29 (17)O41A—S4A—O43A—K3xii−111.70 (15)
O2W—K3—S4B—O42B−18.15 (16)O41A—S4A—O43A—K1x−15.01 (18)
O2W—K3—S4B—O43B77.0 (2)O42A—S4A—O43A—K3xii16.77 (18)
O2W—K3—S4B—C4B−109.31 (18)O42A—S4A—O43A—K1x113.45 (15)
O41B—K3—S4B—O42B174.6 (2)C4A—S4A—O43A—K3xii131.69 (15)
O41B—K3—S4B—O43B−90.3 (2)C4A—S4A—O43A—K1x−131.62 (15)
O41B—K3—S4B—C4B83.4 (2)O41A—S4A—C4A—C3A59.0 (4)
O42B—K3—S4B—O41B−174.6 (2)O41A—S4A—C4A—C5A−122.4 (4)
O42B—K3—S4B—O43B95.2 (2)O42A—S4A—C4A—C3A−60.9 (4)
O42B—K3—S4B—C4B−91.2 (2)O42A—S4A—C4A—C5A117.7 (4)
O42Aiii—K3—S4B—O41B96.94 (16)O43A—S4A—C4A—C3A179.8 (3)
O42Aiii—K3—S4B—O42B−88.50 (16)O43A—S4A—C4A—C5A−1.6 (4)
O42Aiii—K3—S4B—O43B6.6 (2)K3—S4B—O41B—K1viii−144.8 (3)
O42Aiii—K3—S4B—C4B−179.66 (18)O42B—S4B—O41B—K3−5.2 (2)
O43Aiii—K3—S4B—O41B50.45 (16)O42B—S4B—O41B—K1viii−150.0 (2)
O43Aiii—K3—S4B—O42B−135.00 (15)O43B—S4B—O41B—K3122.13 (18)
O43Aiii—K3—S4B—O43B−39.9 (2)O43B—S4B—O41B—K1viii−22.7 (3)
O43Aiii—K3—S4B—C4B133.85 (17)C4B—S4B—O41B—K3−119.08 (16)
O2Wviii—K3—S4B—O41B−24.14 (17)C4B—S4B—O41B—K1viii96.1 (2)
O2Wviii—K3—S4B—O42B150.41 (16)O41B—S4B—O42B—K34.44 (17)
O2Wviii—K3—S4B—O43B−114.4 (2)O43B—S4B—O42B—K3−124.95 (15)
O2Wviii—K3—S4B—C4B59.26 (18)C4B—S4B—O42B—K3118.76 (15)
S4Bix—K3—S4B—O41B−120.20 (16)K3—S4B—O43B—K1−44.0 (2)
S4Bix—K3—S4B—O42B54.36 (14)K3—S4B—O43B—K1xiii60.7 (3)
S4Bix—K3—S4B—O43B149.50 (19)O41B—S4B—O43B—K1−100.68 (18)
S4Bix—K3—S4B—C4B−36.80 (17)O41B—S4B—O43B—K1xiii4.0 (3)
O41Bix—K3—S4B—O41B−96.17 (17)O42B—S4B—O43B—K126.9 (2)
O41Bix—K3—S4B—O42B78.38 (16)O42B—S4B—O43B—K1xiii131.6 (3)
O41Bix—K3—S4B—O43B173.5 (2)C4B—S4B—O43B—K1141.61 (16)
O41Bix—K3—S4B—C4B−12.77 (19)C4B—S4B—O43B—K1xiii−113.7 (3)
O42Bix—K3—S4B—O41B−140.37 (17)K3—S4B—C4B—C3B142.0 (3)
O42Bix—K3—S4B—O42B34.19 (16)K3—S4B—C4B—C5B−36.5 (5)
O42Bix—K3—S4B—O43B129.3 (2)O41B—S4B—C4B—C3B−166.4 (3)
O42Bix—K3—S4B—C4B−56.97 (18)O41B—S4B—C4B—C5B15.1 (5)
O42Avii—K3—S4B—O41B152.50 (19)O42B—S4B—C4B—C3B75.4 (4)
O42Avii—K3—S4B—O42B−32.95 (18)O42B—S4B—C4B—C5B−103.1 (5)
O42Avii—K3—S4B—O43B62.2 (2)O43B—S4B—C4B—C3B−43.0 (4)
O42Avii—K3—S4B—C4B−124.1 (2)O43B—S4B—C4B—C5B138.5 (4)
S4B—K3—O2W—K2−122.40 (3)C2A—C1A—C1B—C2B3.0 (6)
O41B—K3—O2W—K2−117.24 (7)C2A—C1A—C1B—C6B−178.3 (5)
O42B—K3—O2W—K2−131.64 (8)C6A—C1A—C1B—C2B−176.3 (4)
S4B—K3—O41B—K1viii153.3 (2)C6A—C1A—C1B—C6B2.5 (7)
O2W—K3—O41B—S4B−12.71 (17)C1B—C1A—C2A—C3A−177.7 (4)
O2W—K3—O41B—K1viii140.62 (11)C6A—C1A—C2A—C3A1.6 (7)
O42B—K3—O41B—S4B3.06 (12)C1B—C1A—C6A—C5A178.1 (5)
O42B—K3—O41B—K1viii156.39 (16)C2A—C1A—C6A—C5A−1.2 (8)
O42Aiii—K3—O41B—S4B−75.87 (15)C1A—C1B—C2B—C3B178.6 (4)
O43Aiii—K3—O41B—S4B−125.62 (17)C6B—C1B—C2B—C3B−0.2 (7)
O2Wviii—K3—O41B—S4B154.69 (18)C1A—C1B—C6B—C5B−178.0 (6)
S4Bix—K3—O41B—S4B70.76 (16)C2B—C1B—C6B—C5B0.8 (9)
O41Bix—K3—O41B—S4B98.52 (16)C1A—C2A—C3A—C4A−0.5 (7)
O42Bix—K3—O41B—S4B43.89 (18)C1B—C2B—C3B—C4B−1.5 (6)
O43Avii—K3—O41B—S4B−165.15 (13)C2A—C3A—C4A—S4A177.5 (4)
O2W—K3—O42B—S4B158.11 (18)C2A—C3A—C4A—C5A−1.1 (7)
O41B—K3—O42B—S4B−2.91 (11)C2B—C3B—C4B—S4B−175.8 (3)
O42Aiii—K3—O42B—S4B83.00 (14)C2B—C3B—C4B—C5B2.7 (7)
O43Aiii—K3—O42B—S4B46.38 (15)S4A—C4A—C5A—C6A−177.1 (4)
O2Wviii—K3—O42B—S4B−33.08 (17)C3A—C4A—C5A—C6A1.5 (7)
S4Bix—K3—O42B—S4B−130.57 (13)S4B—C4B—C5B—C6B176.4 (5)
O41Bix—K3—O42B—S4B−114.34 (14)C3B—C4B—C5B—C6B−2.1 (9)
O42Bix—K3—O42B—S4B−144.75 (16)C4A—C5A—C6A—C1A−0.3 (8)
O42Avii—K3—O42B—S4B158.31 (12)C4B—C5B—C6B—C1B0.4 (10)
Symmetry codes: (i) x−1, y, z; (ii) x−1, y, z+1; (iii) x, y, z+1; (iv) x−1/2, −y+1/2, z; (v) x−1/2, −y+1/2, z+1; (vi) x−1, −y, z+1; (vii) x, −y, z+1; (viii) x+1, y, z; (ix) x, −y, z; (x) x+1, y, z−1; (xi) x+1/2, −y+1/2, z−1; (xii) x, y, z−1; (xiii) x+1/2, −y+1/2, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H11W···O4Wiii0.972.182.778 (9)119
O2W—H2W···O42B0.961.912.840 (5)162
O3W—H3W···O42B0.961.952.884 (5)162
O4W—H41W···O3W0.901.822.715 (9)180
O4W—H41W···O3W0.901.822.715 (9)180
C5A—H5A···O43A0.952.502.916 (5)106
C5B—H5B···O41B0.942.472.873 (5)106
Symmetry codes: (iii) x, y, z+1.
Selected geometric parameters (Å, °) top
K1—O43B2.850 (4)K2—O42Avii2.741 (3)
K1—O41Bi2.703 (3)K3—O2W3.079 (4)
K1—O41Aii3.040 (4)K3—O41B2.751 (3)
K1—O43Aii3.058 (3)K3—O42B3.076 (4)
K1—O42Aiii2.866 (3)K3—O42Aiii2.938 (3)
K1—O43Biv2.739 (3)K3—O43Aiii3.027 (3)
K1—O41Av2.681 (3)K3—O2Wviii2.793 (4)
K2—O1W2.703 (6)K3—O41Bix2.751 (3)
K2—O2W2.866 (5)K3—O42Bix3.076 (4)
K2—O43Aii2.657 (3)K3—O42Avii2.938 (3)
K2—O42Aiii2.741 (3)K3—O43Avii3.027 (3)
K2—O43Avi2.657 (3)
O41Bi—K1—O43B110.25 (9)O41B—K3—O42B48.53 (9)
O41Aii—K1—O43B160.66 (9)O41B—K3—O42Aiii75.26 (9)
O43Aii—K1—O43B152.59 (10)O41B—K3—O43Aiii71.01 (8)
O42Aiii—K1—O43B83.81 (9)O2Wviii—K3—O41B72.58 (8)
O43B—K1—O43Biv71.84 (10)S4Bix—K3—O41B121.69 (7)
O41Av—K1—O43B95.63 (10)O41B—K3—O41Bix121.19 (10)
O41Aii—K1—O41Bi72.70 (9)O41B—K3—O42Bix113.82 (9)
O41Bi—K1—O43Aii71.13 (9)O41B—K3—O42Avii162.77 (10)
O41Bi—K1—O42Aiii118.54 (10)O41B—K3—O43Avii138.51 (9)
O41Bi—K1—O43Biv80.84 (10)O42Aiii—K3—O42B72.09 (8)
O41Av—K1—O41Bi139.11 (11)O42B—K3—O43Aiii103.14 (9)
O41Aii—K1—O43Aii46.73 (8)O2Wviii—K3—O42B115.52 (10)
O41Aii—K1—O42Aiii112.09 (9)S4Bix—K3—O42B96.07 (7)
O41Aii—K1—O43Biv90.23 (10)O41Bix—K3—O42B113.82 (9)
O41Aii—K1—O41Av72.92 (10)O42B—K3—O42Bix75.45 (9)
O42Aiii—K1—O43Aii72.58 (9)O42Avii—K3—O42B122.82 (10)
O43Aii—K1—O43Biv133.53 (10)O42B—K3—O43Avii169.11 (9)
O41Av—K1—O43Aii99.88 (9)O42Aiii—K3—O43Aiii47.64 (8)
O42Aiii—K1—O43Biv153.45 (10)O2Wviii—K3—O42Aiii120.66 (8)
O41Av—K1—O42Aiii94.61 (10)S4Bix—K3—O42Aiii145.18 (7)
O41Av—K1—O43Biv77.83 (9)O41Bix—K3—O42Aiii162.77 (10)
O1W—K2—O2W178.76 (17)O42Aiii—K3—O42Bix122.82 (10)
O1W—K2—O43Aii101.02 (12)O42Aiii—K3—O42Avii87.93 (9)
O1W—K2—O42Aiii105.61 (11)O42Aiii—K3—O43Avii100.51 (9)
O1W—K2—O43Avi101.02 (12)O2Wviii—K3—O43Aiii75.00 (9)
O1W—K2—O42Avii105.61 (11)S4Bix—K3—O43Aiii160.55 (7)
O2W—K2—O43Aii79.84 (9)O41Bix—K3—O43Aiii138.51 (9)
O2W—K2—O42Aiii73.61 (8)O42Bix—K3—O43Aiii169.11 (9)
O2W—K2—O43Avi79.84 (9)O42Avii—K3—O43Aiii100.51 (9)
O2W—K2—O42Avii73.61 (8)O43Aiii—K3—O43Avii76.15 (9)
O42Aiii—K2—O43Aii81.09 (9)S4Bix—K3—O2Wviii94.10 (6)
O43Aii—K2—O43Avi89.26 (10)O2Wviii—K3—O41Bix72.58 (8)
O42Avii—K2—O43Aii152.93 (10)O2Wviii—K3—O42Bix115.52 (10)
O42Aiii—K2—O43Avi152.93 (10)O2Wviii—K3—O42Avii120.66 (8)
O42Aiii—K2—O42Avii96.15 (10)O2Wviii—K3—O43Avii75.00 (9)
O42Avii—K2—O43Avi81.09 (9)S4Bix—K3—O41Bix23.63 (6)
S4B—K3—O2W78.47 (5)S4Bix—K3—O42Bix24.96 (7)
S4B—K3—O41B23.63 (6)S4Bix—K3—O42Avii70.87 (6)
S4B—K3—O42B24.96 (7)S4Bix—K3—O43Avii85.56 (6)
S4B—K3—O42Aiii70.87 (6)O41Bix—K3—O42Bix48.53 (9)
S4B—K3—O43Aiii85.56 (6)O41Bix—K3—O42Avii75.26 (9)
S4B—K3—O2Wviii94.10 (6)O41Bix—K3—O43Avii71.01 (8)
S4B—K3—S4Bix111.64 (4)O42Avii—K3—O42Bix72.09 (8)
S4B—K3—O41Bix121.69 (7)O42Bix—K3—O43Avii103.14 (9)
S4B—K3—O42Bix96.07 (7)O42Avii—K3—O43Avii47.64 (8)
S4B—K3—O42Avii145.18 (7)K2—O2W—K380.85 (11)
S4B—K3—O43Avii160.55 (7)K2—O2W—K3i85.61 (12)
O2W—K3—O41B101.53 (8)K3—O2W—K3i166.45 (17)
O2W—K3—O42B54.96 (9)K1x—O41A—K1xi85.21 (9)
O2W—K3—O42Aiii67.86 (8)K1viii—O41B—K3111.44 (10)
O2W—K3—O43Aiii115.20 (9)K1xii—O42A—K2xii100.58 (10)
O2W—K3—O2Wviii166.45 (13)K1xii—O42A—K3xii113.15 (10)
S4Bix—K3—O2W78.47 (5)K2xii—O42A—K3xii85.52 (10)
O2W—K3—O41Bix101.53 (8)K1x—O43A—K3xii95.55 (9)
O2W—K3—O42Bix54.96 (9)K2x—O43A—K3xii84.90 (9)
O2W—K3—O42Avii67.86 (8)K1x—O43A—K2x97.79 (9)
O2W—K3—O43Avii115.20 (9)K1—O43B—K1xiii87.96 (9)
Symmetry codes: (i) x−1, y, z; (ii) x−1, y, z+1; (iii) x, y, z+1; (iv) x−1/2, −y+1/2, z; (v) x−1/2, −y+1/2, z+1; (vi) x−1, −y, z+1; (vii) x, −y, z+1; (viii) x+1, y, z; (ix) x, −y, z; (x) x+1, y, z−1; (xi) x+1/2, −y+1/2, z−1; (xii) x, y, z−1; (xiii) x+1/2, −y+1/2, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H11W···O4Wiii0.972.182.778 (9)119
O2W—H2W···O42B0.961.912.840 (5)162
O3W—H3W···O42B0.961.952.884 (5)162
O4W—H41W···O3W0.901.822.715 (9)180
O4W—H41W···O3W0.901.822.715 (9)180
C5A—H5A···O43A0.952.502.916 (5)106
C5B—H5B···O41B0.942.472.873 (5)106
Symmetry codes: (iii) x, y, z+1.
Acknowledgements top

The authors acknowledge financial support from the School of Physical and Chemical Sciences, Queensland University of Technology, and the School of Biomolecular and Physical Sciences, Griffith University.

references
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