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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): m834–m835.
Published online 2010 June 23. doi:  10.1107/S160053681002341X
PMCID: PMC3006948

catena-Poly[[[aqua(7-hydroxy-2H-1-benzopyran-2-one)sodium]-di-μ-aqua] 2-oxo-2H-1-benzopyran-7-olate monohydrate]

Abstract

The asymmetric unit of the title compound, {[Na(C9H6O3)(H2O)3](C9H5O3)·H2O}n, contains two crystallographically independent Na atoms, two 7-hy­droxy­coumarin ligands, six coordinated water mol­ecules, two 7-hy­droxy­coumarin anions and two uncoordinated water mol­ecules. Both Na atoms exhibit a distorted octa­hedral coordination geometry and are coordinated by five water O atoms and the terminal O atom from a 7-hy­droxy­coumarin ligand. Four of the water mol­ecules are bridging, whereas the fifth is terminal. Na—O bond distances are in the range 2.288 (2)–2.539 (2) Å. In the chains, extending parallel to [100], adjacent Na atoms are separated by 3.60613 (7) Å. The uncoordinated water mol­ecules and 7-hy­droxy­coumarin phenolate anions are located between the chains and are hydrogen bonded to the chains.

Related literature

For applications of the active drug umbelliferone (7-hy­droxy­coumarin, 7-HOC), see: Toyama et al. (2009 [triangle]); Egan et al. (1990 [triangle]). For applications of metal complexes of coumarin, see: Nath et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m834-scheme1.jpg

Experimental

Crystal data

  • [Na(C9H6O3)(H2O)3](C9H5O3)·H2O
  • M r = 836.64
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m834-efi1.jpg
  • a = 11.7803 (5) Å
  • b = 7.6462 (3) Å
  • c = 42.3249 (17) Å
  • β = 102.184 (1)°
  • V = 3726.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 173 K
  • 0.46 × 0.44 × 0.39 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.938, T max = 0.947
  • 16682 measured reflections
  • 7251 independent reflections
  • 5790 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.153
  • S = 1.13
  • 7251 reflections
  • 573 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2003 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681002341X/rk2209sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002341X/rk2209Isup2.hkl

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

Acknowledgments

This work was supported by a grant from the National Natural Science Foundation of China (No. 30973922).

supplementary crystallographic information

Comment

It has been suggested that coumarin (1,2-benzopyrone) may be a pro-drug and its major biotransformed product 7-hydroxycoumarin, also known as umbelliferone, is an active drug (Egan et al., 1990). The 7-hydroxycoumarin is also a widely distributed natural product which shows anti-imflammatory activity (Toyama et al., 2009), and the complexes of coumarin with metal have increased bioactivities such as anti-imflammatory activity (Nath et al., 2005). We synthesized the complexe of 7-hydroxycoumarin with sodium for further bioactivities study. This paper is devoted to the crystal structure of the sodium salt of 7-hydroxycoumarin.

The molecular structure of the title compound is shown in Fig. 1. The main moiety of crystal structure is build up of cation chains - (C18H24Na2O12)2+n. The polymeric chain contains two independent crystallographic Na centers. Both Na atoms is six-coordinated by five O atoms of water molecules and one O atom of a ligand. Each 7-hydroxycoumarin ligand links Na centers via its O atom of carbonyl group in a chelating manner. Oxygen atoms of two water are bridging atom between two sodium atoms. Na—O bond distances are in the range of 2.288 (2)–2.539 (2)Å. In the chain, two adjacent Na1···Na2 distance of 3.60613 (7)Å. In addition, two 7-hydroxycoumarin anions and two water molecules are hydrogen bonded to the chains.

Experimental

A stoichiometric amount of NaOH (0.25 mmol) and a quantitative amount of 7-hydroxycoumarin (0.5 mmol) were mixed and then dissolved in ethanol (20 ml). The pH value of the solution was about to 6.5. The solution mixture was stirred continuously for 2 h at room temperature and then filtered. Single crystals were obtained by evaporation after one week.

Refinement

Hydrogen atoms of the water molecules were located from a difference map and were refined isotropically. The C-bound H-atoms were positioned geometrically and refined using a riding model: C—H = 0.95Å with Uiso(H) = 1.2Ueq(C). The hydroxy O-bound H-atoms were positioned geometrically and refined using a riding model: O—H = 0.84Å with Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
A portion of the infinite chain of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 50% probability level. The H atoms are presented as a small spheres of arbitrary radius.

Crystal data

[Na(C9H6O3)(H2O)3](C9H5O3)·H2OF(000) = 1744
Mr = 418.32Dx = 1.491 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 8701 reflections
a = 11.7803 (5) Åθ = 2.4–27.0°
b = 7.6462 (3) ŵ = 0.14 mm1
c = 42.3249 (17) ÅT = 173 K
β = 102.184 (1)°Block, yellow
V = 3726.5 (3) Å30.46 × 0.44 × 0.39 mm
Z = 8

Data collection

Bruker SMART 1000 CCD diffractometer7251 independent reflections
Radiation source: fine-focus sealed tube5790 reflections with I > 2σ(I)
graphiteRint = 0.027
[var phi]– and ω–scansθmax = 26.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −14→10
Tmin = 0.938, Tmax = 0.947k = −9→4
16682 measured reflectionsl = −43→52

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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.13w = 1/[σ2(Fo2) + (0.0397P)2 + 6.7016P] where P = (Fo2 + 2Fc2)/3
7251 reflections(Δ/σ)max < 0.001
573 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = −0.31 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
O10.23526 (16)0.8756 (3)0.13635 (4)0.0257 (4)
C20.1713 (2)0.9338 (4)0.15762 (6)0.0257 (6)
C30.0611 (2)1.0154 (4)0.14468 (7)0.0281 (6)
H30.01561.05920.15900.034*
C40.0218 (2)1.0302 (4)0.11256 (7)0.0261 (6)
H4−0.05051.08620.10450.031*
C50.0514 (2)0.9665 (4)0.05654 (7)0.0291 (6)
H5−0.02111.01820.04700.035*
C60.1193 (3)0.8967 (4)0.03704 (7)0.0301 (6)
H60.09400.90040.01420.036*
C70.2261 (2)0.8199 (4)0.05101 (7)0.0279 (6)
C80.2640 (2)0.8138 (4)0.08425 (6)0.0245 (6)
H80.33640.76160.09370.029*
C90.1945 (2)0.8848 (4)0.10340 (6)0.0220 (6)
C100.0873 (2)0.9629 (4)0.09044 (6)0.0235 (6)
O110.29631 (18)0.7479 (3)0.03313 (5)0.0401 (6)
H110.26430.75390.01340.060*
O120.21478 (18)0.9155 (3)0.18627 (5)0.0335 (5)
O130.26587 (16)0.7216 (3)0.36781 (4)0.0262 (4)
C140.3302 (2)0.6748 (4)0.34559 (7)0.0256 (6)
C150.4381 (2)0.5838 (4)0.35722 (7)0.0288 (6)
H150.48380.54870.34230.035*
C160.4752 (2)0.5479 (4)0.38881 (7)0.0270 (6)
H160.54560.48540.39590.032*
C170.4438 (2)0.5750 (4)0.44534 (7)0.0276 (6)
H170.51470.51610.45380.033*
C180.3760 (2)0.6316 (4)0.46607 (7)0.0287 (6)
H180.40010.61190.48870.034*
C190.2712 (2)0.7186 (4)0.45381 (7)0.0278 (6)
C200.2354 (2)0.7486 (4)0.42082 (6)0.0257 (6)
H200.16460.80800.41240.031*
C210.3050 (2)0.6901 (4)0.40041 (6)0.0227 (6)
C220.4097 (2)0.6028 (3)0.41194 (7)0.0236 (6)
O230.20131 (19)0.7771 (3)0.47295 (5)0.0395 (6)
H230.23140.75440.49230.059*
O240.28986 (18)0.7130 (3)0.31755 (5)0.0330 (5)
O250.26302 (16)0.3348 (3)0.08489 (4)0.0278 (4)
C260.2189 (3)0.3358 (4)0.05220 (7)0.0297 (6)
C270.1023 (3)0.3955 (4)0.04096 (7)0.0344 (7)
H270.06970.39670.01840.041*
C280.0378 (3)0.4502 (4)0.06194 (7)0.0331 (7)
H28−0.03920.49050.05400.040*
C290.0240 (3)0.5025 (4)0.11978 (8)0.0324 (7)
H29−0.05370.54320.11340.039*
C300.0755 (3)0.4976 (4)0.15192 (7)0.0317 (7)
H300.03320.53630.16740.038*
C310.1910 (2)0.4359 (4)0.16264 (7)0.0265 (6)
C320.2516 (2)0.3821 (4)0.13896 (7)0.0255 (6)
H320.32920.34080.14520.031*
C330.1980 (2)0.3895 (4)0.10683 (6)0.0234 (6)
C340.0839 (2)0.4482 (4)0.09587 (7)0.0282 (6)
O350.23967 (17)0.4289 (3)0.19366 (5)0.0304 (5)
O360.28529 (18)0.2832 (3)0.03552 (5)0.0381 (5)
O370.76263 (16)0.2269 (3)0.07958 (4)0.0288 (5)
C380.7208 (3)0.2060 (4)0.04703 (7)0.0304 (7)
C390.6054 (3)0.1389 (4)0.03655 (7)0.0339 (7)
H390.57430.12360.01410.041*
C400.5402 (3)0.0973 (4)0.05811 (8)0.0331 (7)
H400.46380.05330.05070.040*
C410.5241 (3)0.0783 (4)0.11626 (8)0.0334 (7)
H410.44660.03630.11040.040*
C420.5743 (3)0.0983 (4)0.14834 (8)0.0317 (7)
H420.53130.06860.16420.038*
C430.6895 (2)0.1626 (4)0.15829 (7)0.0260 (6)
C440.7499 (2)0.2065 (4)0.13408 (7)0.0260 (6)
H440.82660.25210.13980.031*
C450.6974 (2)0.1832 (4)0.10207 (7)0.0247 (6)
C460.5847 (2)0.1184 (4)0.09187 (7)0.0277 (6)
O470.73790 (17)0.1803 (3)0.18917 (5)0.0320 (5)
O480.78815 (18)0.2480 (3)0.02986 (5)0.0390 (5)
O1W0.10600 (19)1.2312 (3)0.22568 (6)0.0340 (5)
H1A0.153 (3)1.290 (5)0.2146 (8)0.041*
H1B0.119 (3)1.275 (5)0.2443 (9)0.041*
O2W0.08624 (18)0.9228 (3)0.28844 (5)0.0296 (5)
H2A0.130 (3)1.013 (5)0.2967 (8)0.036*
H2B0.122 (3)0.835 (5)0.2963 (8)0.036*
O3W0.17663 (18)0.6416 (3)0.24113 (5)0.0288 (5)
H3A0.182 (3)0.584 (5)0.2253 (8)0.035*
H3B0.148 (3)0.574 (5)0.2525 (8)0.035*
O4W0.32795 (19)0.9807 (3)0.26292 (5)0.0306 (5)
H4A0.358 (3)1.057 (5)0.2509 (8)0.037*
H4B0.315 (3)1.043 (5)0.2787 (8)0.037*
O5W0.3969 (2)0.3917 (3)0.27914 (6)0.0382 (6)
H5A0.454 (3)0.344 (5)0.2824 (9)0.046*
H5B0.358 (3)0.338 (5)0.2912 (9)0.046*
O6W0.58882 (18)0.6911 (3)0.28677 (5)0.0293 (5)
H6A0.624 (3)0.602 (5)0.2951 (8)0.035*
H6B0.636 (3)0.769 (5)0.2949 (8)0.035*
O7W0.4008 (2)0.1863 (4)0.21454 (6)0.0451 (6)
H7A0.382 (4)0.104 (6)0.2044 (10)0.054*
H7B0.344 (3)0.272 (5)0.2073 (9)0.054*
O8W0.1042 (2)0.4173 (4)0.28519 (6)0.0444 (6)
H8A0.043 (4)0.370 (5)0.2869 (9)0.053*
H8B0.159 (3)0.349 (5)0.2979 (9)0.053*
Na10.12359 (9)0.92812 (14)0.23211 (3)0.0257 (3)
Na20.37973 (9)0.69032 (14)0.27077 (3)0.0251 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0223 (10)0.0322 (11)0.0216 (9)0.0050 (8)0.0025 (8)0.0016 (8)
C20.0273 (14)0.0271 (14)0.0229 (14)−0.0006 (12)0.0062 (11)−0.0016 (11)
C30.0247 (14)0.0322 (15)0.0285 (15)0.0032 (12)0.0084 (12)−0.0009 (12)
C40.0209 (14)0.0254 (14)0.0313 (15)0.0031 (11)0.0037 (11)−0.0020 (12)
C50.0232 (14)0.0316 (16)0.0294 (15)0.0035 (12)−0.0014 (11)0.0021 (12)
C60.0295 (15)0.0360 (16)0.0222 (14)0.0015 (13)−0.0002 (12)0.0017 (12)
C70.0266 (15)0.0315 (15)0.0261 (14)0.0002 (12)0.0069 (11)−0.0013 (12)
C80.0184 (13)0.0273 (14)0.0270 (14)0.0026 (11)0.0026 (11)0.0012 (12)
C90.0214 (13)0.0227 (13)0.0204 (13)−0.0019 (11)0.0014 (10)0.0010 (11)
C100.0196 (13)0.0243 (14)0.0257 (14)0.0004 (11)0.0032 (11)0.0013 (11)
O110.0342 (12)0.0614 (16)0.0245 (10)0.0128 (11)0.0057 (9)−0.0046 (11)
O120.0357 (12)0.0416 (13)0.0224 (10)0.0074 (10)0.0042 (9)0.0032 (9)
O130.0241 (10)0.0314 (11)0.0225 (10)0.0052 (8)0.0034 (8)0.0023 (8)
C140.0275 (14)0.0242 (14)0.0258 (14)−0.0016 (12)0.0071 (11)0.0004 (11)
C150.0259 (15)0.0279 (15)0.0339 (15)0.0017 (12)0.0089 (12)−0.0019 (12)
C160.0196 (13)0.0249 (14)0.0351 (15)−0.0011 (11)0.0025 (11)0.0021 (12)
C170.0222 (14)0.0282 (15)0.0297 (15)−0.0002 (12)−0.0011 (11)0.0029 (12)
C180.0290 (15)0.0325 (16)0.0222 (14)−0.0032 (13)−0.0002 (11)0.0055 (12)
C190.0269 (14)0.0307 (15)0.0258 (14)−0.0034 (12)0.0054 (11)−0.0004 (12)
C200.0190 (13)0.0304 (15)0.0263 (14)0.0009 (12)0.0017 (11)0.0009 (12)
C210.0209 (13)0.0238 (13)0.0216 (13)−0.0037 (11)0.0008 (10)0.0029 (11)
C220.0208 (13)0.0188 (13)0.0299 (14)−0.0028 (11)0.0026 (11)0.0020 (11)
O230.0358 (12)0.0591 (15)0.0242 (10)0.0091 (11)0.0078 (9)0.0017 (11)
O240.0351 (11)0.0403 (12)0.0234 (10)0.0050 (10)0.0059 (9)0.0011 (9)
O250.0218 (10)0.0370 (11)0.0248 (10)0.0010 (9)0.0051 (8)0.0004 (9)
C260.0284 (15)0.0350 (16)0.0248 (14)−0.0039 (13)0.0036 (12)0.0028 (12)
C270.0323 (16)0.0403 (18)0.0269 (15)0.0021 (14)−0.0027 (12)0.0065 (13)
C280.0243 (15)0.0323 (16)0.0392 (17)0.0038 (13)−0.0009 (13)0.0041 (14)
C290.0252 (15)0.0283 (15)0.0449 (18)0.0045 (12)0.0105 (13)0.0026 (13)
C300.0308 (16)0.0290 (15)0.0387 (17)0.0020 (13)0.0149 (13)−0.0026 (13)
C310.0289 (15)0.0225 (14)0.0291 (15)−0.0051 (12)0.0086 (12)−0.0017 (12)
C320.0186 (13)0.0284 (15)0.0296 (14)0.0000 (11)0.0051 (11)0.0009 (12)
C330.0224 (14)0.0218 (13)0.0270 (14)−0.0011 (11)0.0073 (11)0.0006 (11)
C340.0233 (14)0.0258 (14)0.0353 (16)0.0001 (12)0.0055 (12)0.0033 (12)
O350.0331 (11)0.0320 (11)0.0273 (10)−0.0018 (9)0.0093 (9)−0.0019 (9)
O360.0334 (12)0.0544 (15)0.0267 (11)0.0030 (11)0.0067 (9)0.0000 (10)
O370.0208 (10)0.0409 (12)0.0239 (10)0.0017 (9)0.0027 (8)−0.0034 (9)
C380.0297 (15)0.0353 (16)0.0241 (14)0.0079 (13)0.0010 (12)−0.0061 (12)
C390.0311 (16)0.0363 (17)0.0293 (15)0.0037 (14)−0.0047 (12)−0.0078 (13)
C400.0237 (15)0.0307 (16)0.0415 (17)0.0017 (13)−0.0009 (13)−0.0039 (13)
C410.0210 (14)0.0297 (16)0.0485 (19)−0.0015 (12)0.0048 (13)−0.0023 (14)
C420.0290 (15)0.0261 (15)0.0420 (17)0.0008 (12)0.0120 (13)0.0063 (13)
C430.0262 (14)0.0207 (14)0.0311 (15)0.0042 (11)0.0065 (12)0.0002 (11)
C440.0193 (13)0.0292 (15)0.0289 (14)0.0004 (11)0.0036 (11)−0.0005 (12)
C450.0207 (13)0.0259 (14)0.0277 (14)0.0049 (11)0.0056 (11)−0.0023 (12)
C460.0218 (14)0.0237 (14)0.0355 (16)0.0022 (11)0.0015 (12)−0.0040 (12)
O470.0313 (11)0.0371 (12)0.0286 (11)0.0023 (9)0.0086 (9)0.0042 (9)
O480.0322 (12)0.0584 (15)0.0269 (11)0.0011 (11)0.0071 (9)−0.0055 (10)
O1W0.0356 (12)0.0305 (12)0.0401 (12)−0.0022 (10)0.0175 (10)−0.0003 (10)
O2W0.0251 (11)0.0322 (12)0.0304 (11)0.0033 (9)0.0030 (8)0.0006 (9)
O3W0.0342 (12)0.0238 (11)0.0300 (11)−0.0007 (9)0.0101 (9)0.0003 (9)
O4W0.0380 (12)0.0269 (11)0.0298 (11)−0.0024 (9)0.0139 (9)0.0000 (9)
O5W0.0362 (13)0.0244 (11)0.0600 (15)0.0047 (10)0.0233 (12)0.0088 (10)
O6W0.0242 (11)0.0293 (11)0.0325 (11)−0.0018 (9)0.0017 (9)−0.0006 (9)
O7W0.0342 (13)0.0483 (15)0.0520 (16)−0.0033 (12)0.0073 (11)0.0151 (12)
O8W0.0278 (12)0.0590 (16)0.0465 (14)−0.0053 (12)0.0082 (10)0.0183 (12)
Na10.0269 (6)0.0251 (6)0.0259 (6)0.0026 (5)0.0074 (4)0.0019 (4)
Na20.0245 (6)0.0259 (6)0.0253 (5)0.0003 (5)0.0059 (4)0.0010 (4)

Geometric parameters (Å, °)

O1—C21.365 (3)C30—H300.9500
O1—C91.378 (3)C31—O351.318 (3)
C2—O121.221 (3)C31—C321.410 (4)
C2—C31.440 (4)C32—C331.375 (4)
C3—C41.345 (4)C32—H320.9500
C3—H30.9500C33—C341.400 (4)
C4—C101.429 (4)O37—C381.371 (3)
C4—H40.9500O37—C451.385 (3)
C5—C61.373 (4)C38—O481.226 (4)
C5—C101.408 (4)C38—C391.433 (4)
C5—H50.9500C39—C401.348 (4)
C6—C71.401 (4)C39—H390.9500
C6—H60.9500C40—C461.423 (4)
C7—O111.351 (3)C40—H400.9500
C7—C81.384 (4)C41—C421.370 (4)
C8—C91.379 (4)C41—C461.407 (4)
C8—H80.9500C41—H410.9500
C9—C101.400 (4)C42—C431.421 (4)
O11—H110.8400C42—H420.9500
O12—Na12.410 (2)C43—O471.318 (3)
O13—C141.374 (3)C43—C441.407 (4)
O13—C211.380 (3)C44—C451.377 (4)
C14—O241.217 (3)C44—H440.9500
C14—C151.442 (4)C45—C461.397 (4)
C15—C161.344 (4)O1W—Na12.338 (2)
C15—H150.9500O1W—H1A0.91 (4)
C16—C221.431 (4)O1W—H1B0.84 (4)
C16—H160.9500O2W—Na1i2.442 (2)
C17—C181.375 (4)O2W—Na12.514 (2)
C17—C221.402 (4)O2W—H2A0.89 (4)
C17—H170.9500O2W—H2B0.83 (4)
C18—C191.402 (4)O3W—Na12.288 (2)
C18—H180.9500O3W—Na22.484 (2)
C19—O231.347 (3)O3W—H3A0.82 (4)
C19—C201.390 (4)O3W—H3B0.83 (4)
C20—C211.385 (4)O4W—Na22.308 (2)
C20—H200.9500O4W—Na12.516 (2)
C21—C221.397 (4)O4W—H4A0.89 (4)
O23—H230.8400O4W—H4B0.86 (4)
O24—Na22.440 (2)O5W—Na22.313 (2)
O25—C261.372 (3)O5W—H5A0.76 (4)
O25—C331.387 (3)O5W—H5B0.86 (4)
C26—O361.226 (4)O6W—Na22.413 (2)
C26—C271.431 (4)O6W—Na2ii2.539 (2)
C27—C281.351 (4)O6W—H6A0.84 (4)
C27—H270.9500O6W—H6B0.84 (4)
C28—C341.424 (4)O7W—H7A0.77 (4)
C28—H280.9500O7W—H7B0.94 (4)
C29—C301.368 (4)O8W—H8A0.83 (4)
C29—C341.413 (4)O8W—H8B0.91 (4)
C29—H290.9500Na1—O2Wi2.442 (2)
C30—C311.421 (4)Na2—O6Wii2.539 (2)
C2—O1—C9121.9 (2)C41—C42—H42119.4
O12—C2—O1116.3 (2)C43—C42—H42119.4
O12—C2—C3125.7 (3)O47—C43—C44121.2 (3)
O1—C2—C3118.0 (2)O47—C43—C42121.0 (3)
C4—C3—C2120.7 (3)C44—C43—C42117.8 (3)
C4—C3—H3119.6C45—C44—C43119.6 (3)
C2—C3—H3119.6C45—C44—H44120.2
C3—C4—C10120.9 (3)C43—C44—H44120.2
C3—C4—H4119.5C44—C45—O37116.4 (2)
C10—C4—H4119.5C44—C45—C46123.4 (3)
C6—C5—C10121.1 (3)O37—C45—C46120.2 (2)
C6—C5—H5119.4C45—C46—C41116.5 (3)
C10—C5—H5119.4C45—C46—C40118.4 (3)
C5—C6—C7119.6 (3)C41—C46—C40125.1 (3)
C5—C6—H6120.2Na1—O1W—H1A120 (2)
C7—C6—H6120.2Na1—O1W—H1B107 (3)
O11—C7—C8116.8 (3)H1A—O1W—H1B106 (3)
O11—C7—C6122.4 (3)Na1i—O2W—Na191.63 (8)
C8—C7—C6120.7 (3)Na1i—O2W—H2A126 (2)
C9—C8—C7118.7 (3)Na1—O2W—H2A99 (2)
C9—C8—H8120.7Na1i—O2W—H2B124 (2)
C7—C8—H8120.7Na1—O2W—H2B102 (2)
O1—C9—C8116.9 (2)H2A—O2W—H2B105 (3)
O1—C9—C10120.7 (2)Na1—O3W—Na298.08 (9)
C8—C9—C10122.4 (2)Na1—O3W—H3A116 (2)
C9—C10—C5117.4 (2)Na2—O3W—H3A105 (2)
C9—C10—C4117.7 (2)Na1—O3W—H3B124 (2)
C5—C10—C4125.0 (3)Na2—O3W—H3B106 (2)
C7—O11—H11109.5H3A—O3W—H3B105 (3)
C2—O12—Na1129.07 (19)Na2—O4W—Na196.65 (8)
C14—O13—C21121.5 (2)Na2—O4W—H4A126 (2)
O24—C14—O13116.5 (2)Na1—O4W—H4A105 (2)
O24—C14—C15125.7 (3)Na2—O4W—H4B120 (2)
O13—C14—C15117.8 (2)Na1—O4W—H4B101 (2)
C16—C15—C14121.1 (3)H4A—O4W—H4B103 (3)
C16—C15—H15119.5Na2—O5W—H5A124 (3)
C14—C15—H15119.5Na2—O5W—H5B122 (3)
C15—C16—C22120.8 (3)H5A—O5W—H5B103 (4)
C15—C16—H16119.6Na2—O6W—Na2ii94.47 (8)
C22—C16—H16119.6Na2—O6W—H6A120 (2)
C18—C17—C22121.0 (3)Na2ii—O6W—H6A104 (2)
C18—C17—H17119.5Na2—O6W—H6B132 (2)
C22—C17—H17119.5Na2ii—O6W—H6B100 (2)
C17—C18—C19119.9 (3)H6A—O6W—H6B101 (3)
C17—C18—H18120.1H7A—O7W—H7B107 (4)
C19—C18—H18120.1H8A—O8W—H8B102 (4)
O23—C19—C20117.0 (3)O3W—Na1—O1W169.46 (10)
O23—C19—C18122.5 (3)O3W—Na1—O1286.77 (8)
C20—C19—C18120.5 (3)O1W—Na1—O1289.40 (8)
C21—C20—C19118.7 (3)O3W—Na1—O2Wi105.29 (9)
C21—C20—H20120.7O1W—Na1—O2Wi85.23 (9)
C19—C20—H20120.7O12—Na1—O2Wi107.59 (8)
O13—C21—C20116.8 (2)O3W—Na1—O2W85.56 (8)
O13—C21—C22121.1 (2)O1W—Na1—O2W95.60 (9)
C20—C21—C22122.1 (2)O12—Na1—O2W163.68 (8)
C21—C22—C17117.9 (3)O2Wi—Na1—O2W88.34 (8)
C21—C22—C16117.7 (2)O3W—Na1—O4W82.46 (8)
C17—C22—C16124.4 (3)O1W—Na1—O4W87.34 (8)
C19—O23—H23109.5O12—Na1—O4W83.30 (8)
C14—O24—Na2128.84 (19)O2Wi—Na1—O4W166.71 (9)
C26—O25—C33121.9 (2)O2W—Na1—O4W81.43 (8)
O36—C26—O25115.3 (3)O3W—Na1—Na1i98.53 (6)
O36—C26—C27126.7 (3)O1W—Na1—Na1i89.38 (6)
O25—C26—C27118.0 (3)O12—Na1—Na1i152.55 (8)
C28—C27—C26120.9 (3)O2Wi—Na1—Na1i45.00 (5)
C28—C27—H27119.5O2W—Na1—Na1i43.37 (5)
C26—C27—H27119.5O4W—Na1—Na1i124.02 (7)
C27—C28—C34120.8 (3)O3W—Na1—Na243.00 (6)
C27—C28—H28119.6O1W—Na1—Na2126.72 (7)
C34—C28—H28119.6O12—Na1—Na282.68 (6)
C30—C29—C34121.3 (3)O2Wi—Na1—Na2147.20 (7)
C30—C29—H29119.3O2W—Na1—Na281.88 (6)
C34—C29—H29119.3O4W—Na1—Na239.47 (5)
C29—C30—C31121.4 (3)Na1i—Na1—Na2119.28 (4)
C29—C30—H30119.3O4W—Na2—O5W169.64 (10)
C31—C30—H30119.3O4W—Na2—O6W105.13 (9)
O35—C31—C32121.1 (3)O5W—Na2—O6W84.73 (9)
O35—C31—C30121.2 (3)O4W—Na2—O2484.36 (8)
C32—C31—C30117.7 (3)O5W—Na2—O2489.13 (9)
C33—C32—C31119.7 (3)O6W—Na2—O24111.35 (8)
C33—C32—H32120.2O4W—Na2—O3W82.79 (8)
C31—C32—H32120.2O5W—Na2—O3W88.46 (9)
C32—C33—O25116.5 (2)O6W—Na2—O3W163.64 (9)
C32—C33—C34123.3 (3)O24—Na2—O3W83.33 (8)
O25—C33—C34120.1 (2)O4W—Na2—O6Wii86.98 (8)
C33—C34—C29116.6 (3)O5W—Na2—O6Wii97.09 (9)
C33—C34—C28118.2 (3)O6W—Na2—O6Wii85.53 (8)
C29—C34—C28125.2 (3)O24—Na2—O6Wii162.54 (8)
C38—O37—C45121.9 (2)O3W—Na2—O6Wii80.56 (7)
O48—C38—O37115.1 (3)O4W—Na2—Na143.88 (6)
O48—C38—C39126.9 (3)O5W—Na2—Na1127.24 (8)
O37—C38—C39117.9 (3)O6W—Na2—Na1146.40 (7)
C40—C39—C38120.9 (3)O24—Na2—Na182.39 (6)
C40—C39—H39119.6O3W—Na2—Na138.92 (5)
C38—C39—H39119.6O6Wii—Na2—Na180.86 (6)
C39—C40—C46120.7 (3)O4W—Na2—Na2ii98.02 (6)
C39—C40—H40119.6O5W—Na2—Na2ii91.26 (6)
C46—C40—H40119.6O6W—Na2—Na2ii44.12 (5)
C42—C41—C46121.5 (3)O24—Na2—Na2ii155.23 (7)
C42—C41—H41119.2O3W—Na2—Na2ii121.44 (7)
C46—C41—H41119.2O6Wii—Na2—Na2ii41.41 (5)
C41—C42—C43121.1 (3)Na1—Na2—Na2ii116.32 (4)
C9—O1—C2—O12178.3 (2)Na2—O3W—Na1—O2W−82.85 (8)
C9—O1—C2—C3−3.5 (4)Na2—O3W—Na1—O4W−0.92 (8)
O12—C2—C3—C4179.3 (3)Na2—O3W—Na1—Na1i−124.35 (7)
O1—C2—C3—C41.3 (4)C2—O12—Na1—O3W117.1 (3)
C2—C3—C4—C101.1 (4)C2—O12—Na1—O1W−72.7 (3)
C10—C5—C6—C70.2 (5)C2—O12—Na1—O2Wi12.1 (3)
C5—C6—C7—O11179.5 (3)C2—O12—Na1—O2W179.2 (3)
C5—C6—C7—C80.0 (5)C2—O12—Na1—O4W−160.1 (3)
O11—C7—C8—C9−179.6 (3)C2—O12—Na1—Na1i14.8 (3)
C6—C7—C8—C90.0 (4)C2—O12—Na1—Na2160.1 (3)
C2—O1—C9—C8−176.7 (2)Na1i—O2W—Na1—O3W−107.39 (9)
C2—O1—C9—C103.2 (4)Na1i—O2W—Na1—O1W83.13 (9)
C7—C8—C9—O1179.9 (2)Na1i—O2W—Na1—O12−169.6 (3)
C7—C8—C9—C10−0.1 (4)Na1i—O2W—Na1—O2Wi−1.91 (12)
O1—C9—C10—C5−179.7 (2)Na1i—O2W—Na1—O4W169.58 (8)
C8—C9—C10—C50.2 (4)Na1i—O2W—Na1—Na2−150.51 (7)
O1—C9—C10—C4−0.7 (4)Na2—O4W—Na1—O3W0.99 (9)
C8—C9—C10—C4179.2 (3)Na2—O4W—Na1—O1W−176.33 (9)
C6—C5—C10—C9−0.2 (4)Na2—O4W—Na1—O12−86.62 (9)
C6—C5—C10—C4−179.1 (3)Na2—O4W—Na1—O2Wi127.7 (4)
C3—C4—C10—C9−1.4 (4)Na2—O4W—Na1—O2W87.60 (9)
C3—C4—C10—C5177.5 (3)Na2—O4W—Na1—Na1i96.23 (7)
O1—C2—O12—Na1−163.33 (18)Na1—O4W—Na2—O5W−33.5 (6)
C3—C2—O12—Na118.6 (4)Na1—O4W—Na2—O6W164.49 (8)
C21—O13—C14—O24−177.8 (2)Na1—O4W—Na2—O24−84.88 (8)
C21—O13—C14—C152.8 (4)Na1—O4W—Na2—O3W−0.91 (8)
O24—C14—C15—C16179.9 (3)Na1—O4W—Na2—O6Wii79.95 (8)
O13—C14—C15—C16−0.8 (4)Na1—O4W—Na2—Na2ii119.96 (7)
C14—C15—C16—C22−1.5 (4)Na2ii—O6W—Na2—O4W−85.92 (9)
C22—C17—C18—C190.0 (4)Na2ii—O6W—Na2—O5W97.29 (9)
C17—C18—C19—O23−180.0 (3)Na2ii—O6W—Na2—O24−175.72 (7)
C17—C18—C19—C20−0.2 (4)Na2ii—O6W—Na2—O3W31.5 (4)
O23—C19—C20—C21−179.9 (3)Na2ii—O6W—Na2—O6Wii−0.27 (12)
C18—C19—C20—C210.3 (4)Na2ii—O6W—Na2—Na1−66.35 (14)
C14—O13—C21—C20177.6 (2)C14—O24—Na2—O4W−127.3 (3)
C14—O13—C21—C22−2.6 (4)C14—O24—Na2—O5W60.7 (3)
C19—C20—C21—O13179.6 (2)C14—O24—Na2—O6W−23.3 (3)
C19—C20—C21—C22−0.2 (4)C14—O24—Na2—O3W149.3 (3)
O13—C21—C22—C17−179.8 (2)C14—O24—Na2—O6Wii172.1 (3)
C20—C21—C22—C170.0 (4)C14—O24—Na2—Na1−171.5 (3)
O13—C21—C22—C160.3 (4)C14—O24—Na2—Na2ii−30.4 (3)
C20—C21—C22—C16−179.9 (3)Na1—O3W—Na2—O4W1.01 (9)
C18—C17—C22—C210.1 (4)Na1—O3W—Na2—O5W175.44 (10)
C18—C17—C22—C16−180.0 (3)Na1—O3W—Na2—O6W−119.2 (3)
C15—C16—C22—C211.7 (4)Na1—O3W—Na2—O2486.13 (9)
C15—C16—C22—C17−178.2 (3)Na1—O3W—Na2—O6Wii−87.11 (9)
O13—C14—O24—Na2171.97 (17)Na1—O3W—Na2—Na2ii−94.02 (7)
C15—C14—O24—Na2−8.7 (4)O3W—Na1—Na2—O4W−178.56 (12)
C33—O25—C26—O36−179.6 (3)O1W—Na1—Na2—O4W4.58 (11)
C33—O25—C26—C270.0 (4)O12—Na1—Na2—O4W88.33 (10)
O36—C26—C27—C28179.9 (3)O2Wi—Na1—Na2—O4W−160.37 (15)
O25—C26—C27—C280.4 (5)O2W—Na1—Na2—O4W−86.36 (10)
C26—C27—C28—C34−0.7 (5)Na1i—Na1—Na2—O4W−109.16 (9)
C34—C29—C30—C31−0.7 (5)O3W—Na1—Na2—O5W−5.73 (12)
C29—C30—C31—O35−178.9 (3)O1W—Na1—Na2—O5W177.41 (11)
C29—C30—C31—C321.0 (4)O12—Na1—Na2—O5W−98.84 (11)
O35—C31—C32—C33179.4 (3)O2Wi—Na1—Na2—O5W12.46 (16)
C30—C31—C32—C33−0.5 (4)O2W—Na1—Na2—O5W86.47 (11)
C31—C32—C33—O25179.9 (2)O4W—Na1—Na2—O5W172.83 (13)
C31—C32—C33—C34−0.2 (4)Na1i—Na1—Na2—O5W63.67 (10)
C26—O25—C33—C32179.8 (3)O3W—Na1—Na2—O6W153.64 (15)
C26—O25—C33—C34−0.1 (4)O1W—Na1—Na2—O6W−23.23 (16)
C32—C33—C34—C290.4 (4)O12—Na1—Na2—O6W60.52 (13)
O25—C33—C34—C29−179.6 (3)O2Wi—Na1—Na2—O6W171.83 (15)
C32—C33—C34—C28179.9 (3)O2W—Na1—Na2—O6W−114.17 (13)
O25—C33—C34—C28−0.2 (4)O4W—Na1—Na2—O6W−27.80 (14)
C30—C29—C34—C330.0 (4)Na1i—Na1—Na2—O6W−136.96 (11)
C30—C29—C34—C28−179.4 (3)O3W—Na1—Na2—O24−88.79 (10)
C27—C28—C34—C330.6 (4)O1W—Na1—Na2—O2494.34 (10)
C27—C28—C34—C29180.0 (3)O12—Na1—Na2—O24178.09 (8)
C45—O37—C38—O48−179.2 (3)O2Wi—Na1—Na2—O24−70.60 (13)
C45—O37—C38—C390.9 (4)O2W—Na1—Na2—O243.40 (8)
O48—C38—C39—C40179.9 (3)O4W—Na1—Na2—O2489.77 (10)
O37—C38—C39—C40−0.2 (4)Na1i—Na1—Na2—O24−19.40 (7)
C38—C39—C40—C46−0.2 (5)O1W—Na1—Na2—O3W−176.86 (13)
C46—C41—C42—C430.8 (5)O12—Na1—Na2—O3W−93.11 (10)
C41—C42—C43—O47−179.4 (3)O2Wi—Na1—Na2—O3W18.19 (14)
C41—C42—C43—C440.5 (4)O2W—Na1—Na2—O3W92.20 (10)
O47—C43—C44—C45178.8 (3)O4W—Na1—Na2—O3W178.56 (12)
C42—C43—C44—C45−1.2 (4)Na1i—Na1—Na2—O3W69.40 (9)
C43—C44—C45—O37−179.1 (2)O3W—Na1—Na2—O6Wii86.26 (10)
C43—C44—C45—C460.6 (4)O1W—Na1—Na2—O6Wii−90.60 (10)
C38—O37—C45—C44178.6 (3)O12—Na1—Na2—O6Wii−6.85 (8)
C38—O37—C45—C46−1.1 (4)O2Wi—Na1—Na2—O6Wii104.45 (13)
C44—C45—C46—C410.7 (4)O2W—Na1—Na2—O6Wii178.46 (8)
O37—C45—C46—C41−179.6 (3)O4W—Na1—Na2—O6Wii−95.18 (10)
C44—C45—C46—C40−179.0 (3)Na1i—Na1—Na2—O6Wii155.66 (6)
O37—C45—C46—C400.7 (4)O3W—Na1—Na2—Na2ii108.28 (9)
C42—C41—C46—C45−1.4 (4)O1W—Na1—Na2—Na2ii−68.58 (9)
C42—C41—C46—C40178.3 (3)O12—Na1—Na2—Na2ii15.17 (7)
C39—C40—C46—C45−0.1 (4)O2Wi—Na1—Na2—Na2ii126.47 (12)
C39—C40—C46—C41−179.7 (3)O2W—Na1—Na2—Na2ii−159.52 (6)
Na2—O3W—Na1—O1W13.9 (6)O4W—Na1—Na2—Na2ii−73.16 (8)
Na2—O3W—Na1—O1282.74 (9)Na1i—Na1—Na2—Na2ii177.68 (3)
Na2—O3W—Na1—O2Wi−169.90 (8)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O8W—H8B···O47ii0.91 (4)1.78 (4)2.658 (3)162 (4)
O8W—H8A···O1Wiii0.83 (4)2.02 (4)2.809 (3)159 (4)
O7W—H7A···O12iv0.77 (4)2.43 (4)3.068 (3)141 (4)
O7W—H7B···O350.94 (4)1.73 (4)2.668 (3)180 (5)
O6W—H6B···O12ii0.84 (4)2.09 (4)2.913 (3)165 (3)
O6W—H6A···O35ii0.84 (4)2.06 (4)2.843 (3)156 (3)
O5W—H5B···O47ii0.86 (4)1.96 (4)2.799 (3)167 (4)
O5W—H5A···O7Wii0.76 (4)2.07 (4)2.819 (3)171 (4)
O4W—H4B···O47v0.86 (4)1.92 (4)2.776 (3)171 (3)
O4W—H4A···O7Wvi0.89 (4)1.98 (4)2.854 (3)164 (3)
O3W—H3B···O8W0.83 (4)1.98 (4)2.796 (3)170 (3)
O3W—H3A···O350.82 (4)2.01 (4)2.804 (3)164 (3)
O2W—H2B···O240.83 (4)2.20 (4)2.932 (3)148 (3)
O2W—H2A···O47v0.89 (4)2.01 (4)2.870 (3)164 (3)
O1W—H1B···O8Wvi0.84 (4)2.08 (4)2.897 (4)164 (3)
O1W—H1A···O35vi0.91 (4)1.83 (4)2.739 (3)174 (3)
O23—H23···O36vii0.841.832.664 (3)175
O11—H11···O48viii0.841.812.641 (3)173

Symmetry codes: (ii) −x+1, y, −z+1/2; (iii) −x, y−1, −z+1/2; (iv) x, y−1, z; (v) −x+1, y+1, −z+1/2; (vi) x, y+1, z; (vii) x, −y+1, z+1/2; (viii) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2209).

References

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