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Lagoden (L·3H2O, where L is Na+·C20H33O6-; sodium 3[beta],16,18-trihydr­oxy-8,13-epi-9,13-epoxy­labdan-15-oate tri­hy­drate) is widely used as an effective haemostatic agent. It has been crystallized from dimethyl­formamide (DMF) as sodium 3[beta],16,18-trihydr­oxy-8,13-epi-9,13-epoxy­labdan-15-oate dimethyl­formamide hemisolvate dihydrate, Na+·C20H33O6-·0.5C3H7NO·2H2O or L2·DMF·4H2O, and the asymmetric unit contains two of the latter formulation. The four symmetry-independent Na+ cations and lagoden anions, one DMF mol­ecule and six of the eight symmetry-independent water mol­ecules assemble into a one-dimensional polymeric structure via dipolar and hydrogen-bonding inter­actions. The lagoden anions coordinate to the Na+ cations via the carboxyl­ate groups and the two primary hydr­oxy groups, whereas the secondary OH groups are solely involved in hydrogen bonding. Two of the four symmetry-independent lagoden anions act in a chelating mode, forming seven-membered chelate rings. The absolute structure, based on anomalous dispersion data collected at 130 K with Cu K[alpha] radiation, confirms an inverted configuration at chiral centres C8 and C13 (labdane numbering) relative to the labdane skeleton.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010903354X/su3037sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010903354X/su3037Isup2.hkl
Contains datablock I

CCDC reference: 755968

Comment top

Plants of the Lagochilus genus (family Lamiaceae), native to Central Asia and the Middle East, have long been used in traditional medicine and are reputed to possess antihaemorrhagic and haemostatic properties. The components responsible for these effects are labdane-type diterpenoids, many of which have been isolated from these plants and have shown haemostatic properties. Lagoden is a synthetic derivative of the naturally occurring diterpenoid lagochirsin (Zainutdinov et al., 1994), which has been isolated from three plants, namely L. gypsaceus, L. hirsutissimus and L. setulosus. It has been developed and approved for public use in Russia, Uzbekistan and some other former Soviet republics. Lagoden is produced as a white crystalline powder that is odourless and non-hygroscopic, and is sold as a 0.5% water solution in ampoules for internal introduction.

The crystal structures of lagochilin in its anhydrous and hydrated forms (Izotova et al., 1997; Vorontsova et al., 1975), lagochirsin (Izotova et al., 2004) and several other labdane-type diterpenoids isolated from plants of the Lagochilus genus, or their derivatives, have been reported over the years (Talipov et al., 2001; Izotova et al., 2000; Zainutdinov et al., 1999). Recently, we succeeded in growing single crystals of lagoden from a dimethylformamide (DMF) solution and we report its crystal structure here as the title compound, (I). Owing to the presence of Na+ ions, the absolute structure of (I) could be determined reliably using Cu Kα radiation.

Single crystals of lagoden proved very difficult to grow, despite efforts over a long time. In most cases, crystallizations resulted in amorphous glassy materials, but from a water–n-butanol mixture well shaped thin plates could be obtained repeatedly, although they diffracted very poorly. Serendipitously, a large prism of compound (I) was found in a small-scale crystallization from a DMF solution that had been left unattended for several months. The structure was initially determined at 100 K using Mo Kα radiation. As revealed by X-ray analysis, this crystal was a pseudomerohedral twin, with a twin law corresponding to a 180° rotation about the direct-space [100] direction (the twin matrix in reciprocal space is 1 0 0 0 -1 0 -0.991 0 -1.000). The structure refined well, revealing most of the important features of the crystal structure except the absolute configuration of lagoden, which was one of the objectives of the X-ray analysis. The anomalous signal originating mostly from Na (Δf'' = 0.025) and O atoms (Δf'' = 0.006) was too weak for reliable absolute structure determination, as reflected by the high s.u. value of the Flack parameter [x = 0.1 (3)] (Flack, 1983). Nevertheless, we noticed that the enantiomer indicated by the Flack parameter as the most probable had the expected chirality, with the C5, C9 and C10 centres corresponding to those of labdane, and the stereochemistry of the C8 and C13 centres being inverted. The Hooft parameter y (Hooft et al., 2008) for this enantiomerically pure crystal was 0.25 (9). As the anomalous dispersions of Na (Δf'' = 0.124) and O (Δf'' = 0.032) are significantly stronger for Cu Kα radiation, the measurements were repeated with an Oxford Diffraction Nova Cu Kα source with a small single crystal cut from the twinned specimen. The Flack parameter x = 0.03 (3) and the Hooft parameter y = 0.030 (8) for Cu Kα radiation indicated that the configurations of the C8 and C13 chiral centres of lagoden are R and S, respectively, and that the remaining centres correspond to the labdane stereochemistry. This feature is typical of all known structurally characterized diterpenoids of the Lagochilus genus, including its most popular member, lagochilin.

The asymmetric unit of compound (I) is shown in Figs. 1 and 2. It consists of four Na+ cations, four carboxylate anions, one DMF molecule and six water molecules coordinating to the Na+ ions, and three solvent molecules (one DMF and two water). The numbering scheme of the diterpenoid follows the IUPAC recommendation for the labdane skeleton (IUPAC Commission on Nomenclature of Organic Compounds, 1999). The four diterpenoid anions (A, B, C and D) exhibit similar conformations, with the largest differences found in the region of the spiro tetrahydrofurane ring and its substituents at C13. Analysis of the endocyclic torsion angles of the five-membered ring indicates a twist form, with the twist axis through atom O3 of the furanoid ring. The methyl substituents on the ring system at C4 and C10 are positioned axially, whereas the O1—H hydroxyl group and the C17 methyl group are in equatorial positions.

Na+ cations, anions and neutral ligands (one DMF and six water molecules) are assembled via dipolar interactions [Na—O distances in the range 2.2860 (12)–2.6656 (14) Å; Table 1] and O—H···O hydrogen bonds (Table 2) into a one-dimensional polymeric structure propagating along the a axis. The hydrophobic parts of the diterpenoid cover the polymer surface on two opposite sides, leaving deep grooves on the remaining two sides. Adjacent polymeric chains along the c axis are bridged by two water molecules, O7W and O8W, which are involved as donors in O—H···O hydrogen bonds to the secondary O1—H hydroxyl groups of the four symmetry-independent anions. In effect, the grooves on opposite sides of the polymer meet to form a channel accommodating both the coordinated and hydrogen-bonded DMF molecules (Fig. 3).

The Na+ cations and their coordinating groups are shown in Fig. 4. The coordination environments of ions Na2 and Na3 are distorted octahedral, with carboxylate atoms O5D and O5A bridging the two metal centres. Cation Na3 has in its coordination sphere exclusively O ligands from four symmetry-independent lagoden anions, whereas ion Na2 has three water molecules and O atoms from anions A and D. These two Na ions, together with ions Na1 and Na4, carboxylate atoms O5C and O5B, and the water molecules O3W and O4W, form a cyclic Na4O4 structure (Fig. 4). Cations Na1 and Na4 are basically pentacoordinated, with ion Na1 additionally including in its coordination environment atom O6B from the asymmetrically chelating carboxylate group of anion B [Na1—O6B(x - 1, y, z) = 2.9399 (15) Å]. The closest distances between the Na ions along the polymeric chain are 3.4807 (8) Å within the Na2O2 cyclic structures and 3.9845 (9) Å in the Na4O4 ring. The Na—O—Na angles at the bridging O atoms range from 94.48 (5)° in the smaller ring up to 138.21 (6)° in the eight-membered cycle.

Lagoden anions C and D act as chelating ligands by coordinating ion Na3 via a carboxylate O atom and the primary hydroxyl group at C16. The seven-membered chelate rings that are formed are strongly puckered. The other two ligands coordinate to Na cations via a carboxylate group and the primary hydroxyl group at C18. The coordination mode of the carboxylate groups of ligands B and C is asymmetric chelating and bridging, whereas in the remaining cases it is only bridging. The secondary OH groups at C3 do not interact with the Na+ ions but act as donors in O—H···O hydrogen bonds to carboxylate groups within the same polymeric structure, and as acceptors of hydrogen bonds from water molecules that bridge adjacent polymeric chains via O—H···O interactions (Table 2).

Experimental top

Lagoden [Source?] (1.2 mg) was dissolved in DMF (1 ml) and placed in a 1.5 ml closed plastic vial. After approximately three months, one colourless prism-shaped crystal of (I) was obtained.

Refinement top

C-bound H atoms were placed in idealized positions, with C—H = 0.93–0.98 Å. O-bound H atoms were located in difference electron-density maps and refined with distance restraints of O—H = 0.82 (2) Å for hydroxyl groups and 0.85 (2) Å for water molecules. The H···H distances in the water molecules were restrained to 1.35 (2) Å. In the final cycles of refinement, all the H atoms were treated as riding on their parent atoms, with Uiso(H) = 1.2Ueq(C,O).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of compound (I), with the ligands C and B, the DMF molecules and water molecule O8W omitted. Displacement ellipsoids are drawn at the 40% probability level. C-bound H atoms have been omitted. Double-dashed lines represent hydrogen bonds.
[Figure 2] Fig. 2. The asymmetric unit of compound (I), with the ligands A and D and water molecule O7W omitted. Displacement ellipsoids are drawn at the 40% probability level. C-bound H atoms have been omitted. Double-dashed lines represent hydrogen bonds.
[Figure 3] Fig. 3. The crystal packing of compound (I), viewed along the a axis. Solvent molecules are represented by van der Waals radii. Small spheres represent Na, O and N atoms.
[Figure 4] Fig. 4. A view of the Na+ cations, together with the coordinating groups [symmetry codes: (i) x - 1, y, z; (ii) x - 2, y, z.]
sodium 3β,16,18-trihydroxy-8,13-epi-9,13-epoxylabdan-15-oate dimethylformamide hemisolvate dihydrate top
Crystal data top
Na+·C20H33O6·0.5C3H7NO·2H2OF(000) = 2016
Mr = 465.04Dx = 1.345 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ybCell parameters from 58666 reflections
a = 10.7614 (2) Åθ = 4.3–76.3°
b = 31.0703 (5) ŵ = 1.01 mm1
c = 14.7131 (3) ÅT = 130 K
β = 110.948 (2)°Prism, colourless
V = 4594.32 (15) Å30.3 × 0.2 × 0.2 mm
Z = 8
Data collection top
Oxford Diffraction SuperNova
diffractometer
18050 independent reflections
Radiation source: Nova Cu X-ray source17865 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.030
ω scansθmax = 76.5°, θmin = 4.4°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
h = 1313
Tmin = 0.655, Tmax = 0.818k = 3833
70056 measured reflectionsl = 1718
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0545P)2 + 1.3939P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.55 e Å3
18050 reflectionsΔρmin = 0.29 e Å3
1143 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.00094 (13)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 8192 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.03 (3)
Crystal data top
Na+·C20H33O6·0.5C3H7NO·2H2OV = 4594.32 (15) Å3
Mr = 465.04Z = 8
Monoclinic, P21Cu Kα radiation
a = 10.7614 (2) ŵ = 1.01 mm1
b = 31.0703 (5) ÅT = 130 K
c = 14.7131 (3) Å0.3 × 0.2 × 0.2 mm
β = 110.948 (2)°
Data collection top
Oxford Diffraction SuperNova
diffractometer
18050 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
17865 reflections with I > 2σ(I)
Tmin = 0.655, Tmax = 0.818Rint = 0.030
70056 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.086Δρmax = 0.55 e Å3
S = 1.03Δρmin = 0.29 e Å3
18050 reflectionsAbsolute structure: Flack (1983), with 8192 Friedel pairs
1143 parametersAbsolute structure parameter: 0.03 (3)
1 restraint
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
Na10.10902 (8)0.75631 (3)0.50850 (6)0.03321 (17)
Na20.27294 (6)0.70357 (2)0.61866 (4)0.01765 (13)
Na30.61256 (6)0.72253 (2)0.68407 (4)0.01754 (13)
Na41.00891 (7)0.72153 (2)0.79370 (5)0.02417 (14)
O1A1.14501 (12)0.61649 (4)0.28884 (9)0.0240 (3)
H1A1.20360.63140.32670.029*
O2A1.12672 (12)0.65194 (4)0.51415 (9)0.0244 (3)
H2OA1.06370.64910.53250.029*
O3A0.69893 (10)0.61338 (3)0.42628 (8)0.0148 (2)
O4A0.67641 (12)0.69657 (4)0.34513 (10)0.0254 (3)
H4A0.65290.71880.36450.030*
O5A0.42888 (11)0.69621 (4)0.54739 (8)0.0192 (2)
O6A0.33094 (11)0.67757 (4)0.39154 (8)0.0173 (2)
C1A0.79493 (16)0.59460 (6)0.26893 (11)0.0178 (3)
H1A10.71880.58560.21330.021*
H1A20.77660.62320.28740.021*
C2A0.91770 (16)0.59651 (6)0.23946 (11)0.0199 (3)
H2A10.93660.56800.22070.024*
H2A20.90020.61550.18390.024*
C3A1.03653 (15)0.61273 (6)0.32299 (11)0.0175 (3)
H3A1.01540.64160.34000.021*
C4A1.07090 (15)0.58429 (5)0.41434 (11)0.0166 (3)
C5A0.94371 (14)0.57600 (5)0.43956 (11)0.0134 (3)
H5A0.92390.60390.46220.016*
C6A0.96823 (16)0.54600 (6)0.52632 (11)0.0187 (3)
H6A11.05030.55380.57830.022*
H6A20.98420.51680.51010.022*
C7A0.85175 (16)0.54788 (6)0.56248 (12)0.0198 (3)
H7A10.84830.57630.58890.024*
H7A20.86640.52710.61460.024*
C8A0.71836 (16)0.53834 (5)0.48175 (12)0.0173 (3)
H8A0.72470.50920.45840.021*
C9A0.69573 (15)0.56911 (5)0.39394 (11)0.0138 (3)
C10A0.81274 (15)0.56354 (5)0.35377 (11)0.0140 (3)
C11A0.55537 (15)0.56377 (5)0.31686 (12)0.0176 (3)
H11A0.55680.56820.25200.021*
H11B0.52070.53530.32040.021*
C12A0.47022 (15)0.59838 (5)0.34137 (12)0.0186 (3)
H12A0.40100.60880.28290.022*
H12B0.42940.58720.38560.022*
C13A0.56962 (15)0.63414 (5)0.38970 (11)0.0155 (3)
C14A0.55672 (15)0.65520 (5)0.47925 (11)0.0180 (3)
H14A0.57300.63310.52880.022*
H14B0.62810.67610.50330.022*
C15A0.42807 (15)0.67786 (5)0.47144 (11)0.0148 (3)
C16A0.56747 (16)0.66739 (5)0.31266 (12)0.0194 (3)
H16A0.56910.65250.25510.023*
H16B0.48510.68360.29450.023*
C17A0.60815 (17)0.53736 (6)0.52475 (13)0.0225 (3)
H17A0.62860.51590.57490.027*
H17B0.52490.53060.47440.027*
H17C0.60190.56500.55190.027*
C18A1.17199 (16)0.60974 (6)0.49978 (12)0.0198 (3)
H18A1.19110.59330.55920.024*
H18B1.25440.61270.48760.024*
C19A1.14154 (16)0.54267 (6)0.40348 (13)0.0229 (3)
H19A1.08260.52580.35100.027*
H19B1.16610.52640.46280.027*
H19C1.21990.54970.38980.027*
C20A0.81056 (16)0.51721 (5)0.31567 (12)0.0192 (3)
H20A0.72060.50910.27830.023*
H20B0.84630.49790.36970.023*
H20C0.86350.51580.27530.023*
O1B0.32630 (12)0.83552 (5)0.28086 (9)0.0279 (3)
H1B0.34910.81890.31530.033*
O2B0.09882 (12)0.83101 (4)0.53474 (9)0.0254 (3)
H2OB0.02900.83910.57620.030*
O3B0.26637 (11)0.83842 (3)0.42626 (7)0.0148 (2)
O4B0.20911 (12)0.75230 (4)0.37516 (9)0.0216 (2)
H4B0.24260.72840.38960.026*
O5B0.67748 (11)0.76372 (4)0.55902 (9)0.0216 (2)
O6B0.60828 (12)0.77376 (4)0.39879 (9)0.0226 (2)
C1B0.01308 (16)0.84514 (6)0.26535 (11)0.0195 (3)
H1B10.03920.84730.20880.023*
H1B20.05000.81870.29910.023*
C2B0.13871 (16)0.84297 (6)0.23133 (11)0.0215 (3)
H2B10.17660.86870.19450.026*
H2B20.17040.81830.18890.026*
C3B0.18349 (15)0.83925 (6)0.31762 (12)0.0196 (3)
H3B0.14630.81260.35240.023*
C4B0.13540 (15)0.87692 (6)0.38934 (12)0.0188 (3)
C5B0.01940 (15)0.88051 (5)0.41918 (11)0.0149 (3)
H5B0.05430.85320.45180.018*
C6B0.08086 (16)0.91517 (5)0.49604 (12)0.0187 (3)
H6B10.05450.94340.46750.022*
H6B20.04810.91190.54910.022*
C7B0.23235 (16)0.91174 (5)0.53525 (12)0.0185 (3)
H7B10.26960.93430.58270.022*
H7B20.25860.88430.56780.022*
C8B0.28791 (16)0.91566 (5)0.45368 (12)0.0180 (3)
H8B0.25570.94310.42080.022*
C9B0.22981 (15)0.87959 (5)0.37720 (11)0.0148 (3)
C10B0.07246 (15)0.88342 (5)0.33341 (11)0.0158 (3)
C11B0.29317 (16)0.87950 (5)0.29856 (12)0.0186 (3)
H11C0.22810.87180.23570.022*
H11D0.32930.90760.29360.022*
C12B0.40445 (16)0.84582 (5)0.33227 (11)0.0184 (3)
H12C0.41480.83130.27700.022*
H12D0.48840.85900.37090.022*
C13B0.35841 (15)0.81417 (5)0.39378 (11)0.0158 (3)
C14B0.46861 (16)0.79859 (5)0.48643 (11)0.0170 (3)
H14C0.49790.82320.52940.020*
H14D0.42850.77850.51820.020*
C15B0.59307 (16)0.77701 (5)0.48001 (11)0.0165 (3)
C16B0.28405 (17)0.77678 (5)0.33052 (12)0.0197 (3)
H16C0.22420.78790.26880.024*
H16D0.34760.75800.31720.024*
C17B0.44005 (17)0.91845 (6)0.49627 (14)0.0234 (3)
H17D0.46640.94230.54070.028*
H17E0.47360.92260.44460.028*
H17F0.47550.89230.53020.028*
C18B0.16969 (16)0.86675 (6)0.48001 (12)0.0234 (4)
H18C0.15060.89190.52180.028*
H18D0.26430.86100.45980.028*
C19B0.21286 (18)0.91856 (6)0.34781 (14)0.0272 (4)
H19D0.21850.92240.28170.033*
H19E0.16750.94270.38610.033*
H19F0.30090.91650.34980.033*
C20B0.03577 (17)0.92573 (6)0.27470 (13)0.0226 (3)
H20D0.09170.92930.23700.027*
H20E0.04840.94960.31860.027*
H20F0.05560.92460.23200.027*
O1C0.15096 (11)0.60367 (4)0.97668 (8)0.0189 (2)
H1C0.08760.61380.93220.023*
O2C0.13234 (11)0.59647 (4)0.73474 (8)0.0191 (2)
H2OC0.08880.61490.75000.023*
O3C0.60861 (10)0.58770 (3)0.84167 (7)0.0134 (2)
O4C0.60342 (12)0.67987 (4)0.82647 (9)0.0224 (2)
H4OC0.55370.69030.85180.027*
O5C0.80957 (11)0.68333 (4)0.70637 (8)0.0182 (2)
O6C0.96960 (11)0.64442 (4)0.81103 (9)0.0214 (2)
C1C0.50773 (15)0.59593 (5)0.99976 (11)0.0153 (3)
H1C10.58880.59891.05620.018*
H1C20.50580.61900.95490.018*
C2C0.38816 (15)0.60067 (5)1.03217 (11)0.0172 (3)
H2C10.39020.57821.07840.021*
H2C20.39210.62831.06390.021*
C3C0.26038 (14)0.59754 (5)0.94426 (11)0.0138 (3)
H3C0.25960.62130.90010.017*
C4C0.24727 (14)0.55490 (5)0.88726 (11)0.0143 (3)
C5C0.37581 (14)0.54763 (5)0.86310 (10)0.0135 (3)
H5C0.37570.57100.81830.016*
C6C0.37228 (16)0.50602 (5)0.80580 (12)0.0199 (3)
H6C10.37630.48130.84710.024*
H6C20.28920.50460.75060.024*
C7C0.48860 (17)0.50450 (6)0.76966 (13)0.0218 (3)
H7C10.48650.47740.73650.026*
H7C20.47920.52750.72310.026*
C8C0.62172 (16)0.50896 (5)0.85269 (12)0.0182 (3)
H8C0.62730.48540.89830.022*
C9C0.62742 (15)0.55160 (5)0.90882 (11)0.0139 (3)
C10C0.51073 (15)0.55251 (5)0.95043 (11)0.0141 (3)
C11C0.76585 (15)0.55929 (6)0.98688 (11)0.0176 (3)
H11E0.75800.57321.04360.021*
H11F0.81290.53231.00680.021*
C12C0.83934 (15)0.58849 (6)0.93879 (11)0.0182 (3)
H12E0.89190.57160.91030.022*
H12F0.89760.60840.98570.022*
C13C0.72794 (14)0.61280 (5)0.85982 (11)0.0141 (3)
C14C0.74595 (15)0.61727 (5)0.76134 (11)0.0163 (3)
H14E0.77160.58950.74350.020*
H14F0.66100.62500.71240.020*
C15C0.84886 (15)0.65047 (5)0.75978 (11)0.0157 (3)
C16C0.70955 (15)0.65734 (5)0.89760 (12)0.0177 (3)
H16E0.69040.65420.95690.021*
H16F0.79120.67370.91290.021*
C17C0.73548 (18)0.50246 (6)0.81462 (14)0.0242 (4)
H17G0.72710.47470.78440.029*
H17H0.81900.50420.86790.029*
H17I0.73180.52440.76780.029*
C18C0.12572 (15)0.55982 (5)0.79191 (11)0.0167 (3)
H18E0.11800.53410.75300.020*
H18F0.04600.56200.80790.020*
C19C0.21264 (17)0.51700 (6)0.94087 (13)0.0212 (3)
H19G0.28000.51411.00430.025*
H19H0.20810.49100.90460.025*
H19I0.12810.52220.94720.025*
C20C0.53759 (16)0.51619 (6)1.02722 (12)0.0206 (3)
H20G0.63050.51571.06660.025*
H20H0.51260.48900.99490.025*
H20I0.48630.52131.06780.025*
O1D1.32037 (11)0.84302 (4)0.94695 (8)0.0201 (2)
H1D1.33760.83250.90180.024*
O2D1.10866 (11)0.84948 (4)0.70680 (8)0.0180 (2)
H2OD1.16520.83050.72320.022*
O3D0.73293 (10)0.85953 (3)0.81794 (7)0.0128 (2)
O4D0.75227 (11)0.76864 (4)0.82348 (9)0.0198 (2)
H4OD0.79920.78520.80640.024*
O5D0.43126 (11)0.75662 (4)0.70699 (8)0.0201 (2)
O6D0.33128 (12)0.80146 (4)0.77681 (9)0.0227 (2)
C1D0.99117 (15)0.85461 (5)0.97734 (11)0.0159 (3)
H1D10.96880.85371.03560.019*
H1D20.94800.83030.93690.019*
C2D1.14156 (15)0.84990 (5)1.00635 (11)0.0168 (3)
H2D11.18590.87331.04930.020*
H2D21.17020.82301.04120.020*
C3D1.17958 (14)0.85034 (5)0.91688 (11)0.0149 (3)
H3D1.13410.82620.87530.018*
C4D1.13631 (14)0.89222 (5)0.85715 (11)0.0139 (3)
C5D0.98379 (14)0.89923 (5)0.83297 (10)0.0130 (3)
H5D0.94050.87490.79120.016*
C6D0.92850 (16)0.93953 (6)0.77120 (13)0.0204 (3)
H6D10.96520.96500.80940.024*
H6D20.95570.93950.71500.024*
C7D0.77707 (17)0.94095 (6)0.73724 (13)0.0217 (3)
H7D10.74040.91720.69310.026*
H7D20.74550.96750.70180.026*
C8D0.72720 (16)0.93820 (5)0.82220 (13)0.0195 (3)
H8D0.76620.96250.86530.023*
C9D0.77905 (15)0.89656 (5)0.88201 (11)0.0144 (3)
C10D0.93597 (14)0.89666 (5)0.92164 (11)0.0137 (3)
C11D0.71819 (15)0.89022 (6)0.96141 (12)0.0181 (3)
H11G0.78250.87721.01910.022*
H11H0.68990.91760.97930.022*
C12D0.59885 (15)0.86016 (6)0.91604 (12)0.0184 (3)
H12G0.58700.84130.96490.022*
H12H0.51790.87660.88570.022*
C13D0.63412 (15)0.83426 (5)0.84005 (11)0.0141 (3)
C14D0.52079 (15)0.82714 (5)0.74216 (11)0.0158 (3)
H14G0.47310.85400.72230.019*
H14H0.55930.81980.69380.019*
C15D0.42142 (14)0.79236 (5)0.74190 (11)0.0152 (3)
C16D0.69695 (15)0.79137 (5)0.88351 (11)0.0162 (3)
H16G0.76630.79670.94610.019*
H16H0.62970.77350.89460.019*
C17D0.57610 (17)0.94410 (6)0.78520 (15)0.0261 (4)
H17J0.55330.97130.75260.031*
H17K0.54590.94330.83920.031*
H17L0.53430.92140.74060.031*
C18D1.16578 (15)0.88714 (5)0.76254 (11)0.0173 (3)
H18G1.13240.91230.72220.021*
H18H1.26140.88630.77900.021*
C19D1.22303 (16)0.93066 (6)0.90932 (12)0.0196 (3)
H19J1.22310.93270.97440.023*
H19K1.18760.95670.87460.023*
H19L1.31240.92650.91150.023*
C20D0.98343 (16)0.93449 (6)0.99387 (12)0.0209 (3)
H20J0.93000.93591.03390.025*
H20K0.97480.96100.95840.025*
H20L1.07490.93021.03420.025*
O1E0.44041 (15)0.70458 (5)0.92456 (10)0.0358 (3)
N1E0.49490 (16)0.73948 (5)1.06861 (11)0.0269 (3)
C1E0.41253 (18)0.72797 (6)0.98094 (13)0.0265 (4)
H1E0.32620.73870.96080.032*
C2E0.6320 (2)0.72571 (11)1.10321 (17)0.0517 (7)
H2E10.63530.69481.10200.062*
H2E20.67610.73571.16860.062*
H2E30.67560.73731.06200.062*
C3E0.4528 (3)0.76764 (8)1.13074 (15)0.0428 (5)
H3E10.35920.77331.10060.051*
H3E20.50120.79421.14030.051*
H3E30.46980.75391.19250.051*
O1F1.08805 (15)0.73647 (5)0.95475 (10)0.0375 (3)
N1F1.06742 (16)0.71574 (5)1.09615 (11)0.0280 (3)
C1F1.0300 (2)0.73634 (7)1.01239 (15)0.0330 (4)
H1F0.95190.75230.99560.040*
C2F0.9897 (2)0.71791 (9)1.15938 (16)0.0414 (5)
H2F10.91550.73691.13140.050*
H2F21.04470.72851.22220.050*
H2F30.95780.68971.16630.050*
C3F1.1843 (3)0.68860 (8)1.12828 (16)0.0425 (5)
H3F11.15780.65901.12610.051*
H3F21.23870.69611.19380.051*
H3F31.23410.69271.08630.051*
O1W0.08655 (17)0.73237 (7)0.36065 (13)0.0546 (5)
H1W10.14620.71300.34570.065*
H1W20.01430.71870.37140.065*
O2W0.10336 (12)0.68089 (4)0.54947 (9)0.0261 (3)
H2W10.15950.66600.50520.031*
H2W20.13380.68140.59540.031*
O3W0.13813 (14)0.76660 (5)0.53687 (10)0.0320 (3)
H3W10.15930.76690.48650.038*
H3W20.18060.78760.57090.038*
O4W0.19933 (12)0.72242 (4)0.75952 (9)0.0248 (3)
H4W10.23050.74750.75840.030*
H4W20.25670.71030.80840.030*
O5W0.34655 (14)0.64496 (5)0.72072 (11)0.0401 (4)
H5W10.42330.63910.76170.048*
H5W20.29460.62800.73540.048*
O6W0.91141 (12)0.78422 (4)0.71228 (9)0.0274 (3)
H6W10.83530.78660.66760.033*
H6W20.95380.80640.70570.033*
O7W1.15627 (19)0.55177 (5)0.14655 (11)0.0439 (4)
H7W11.15820.57050.18910.053*
H7W21.14940.56640.09610.053*
O8W0.50041 (18)0.89331 (6)0.12057 (12)0.0512 (4)
H8W10.54420.87680.07400.061*
H8W20.45520.87630.16540.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Na10.0432 (4)0.0265 (4)0.0355 (4)0.0062 (3)0.0208 (3)0.0032 (3)
Na20.0179 (3)0.0179 (3)0.0184 (3)0.0027 (2)0.0081 (2)0.0037 (2)
Na30.0155 (3)0.0171 (3)0.0200 (3)0.0019 (2)0.0063 (2)0.0012 (2)
Na40.0221 (3)0.0230 (4)0.0271 (3)0.0026 (3)0.0085 (3)0.0032 (3)
O1A0.0216 (6)0.0324 (7)0.0225 (6)0.0102 (5)0.0134 (5)0.0088 (5)
O2A0.0212 (6)0.0260 (7)0.0286 (6)0.0065 (5)0.0120 (5)0.0134 (5)
O3A0.0122 (5)0.0123 (5)0.0180 (5)0.0009 (4)0.0032 (4)0.0045 (4)
O4A0.0241 (6)0.0153 (6)0.0408 (7)0.0004 (5)0.0165 (5)0.0027 (5)
O5A0.0202 (5)0.0204 (6)0.0197 (5)0.0007 (4)0.0103 (4)0.0047 (4)
O6A0.0163 (5)0.0153 (6)0.0193 (5)0.0005 (4)0.0051 (4)0.0017 (4)
C1A0.0176 (7)0.0211 (8)0.0141 (7)0.0008 (6)0.0050 (6)0.0014 (6)
C2A0.0211 (8)0.0252 (9)0.0138 (7)0.0026 (6)0.0066 (6)0.0019 (6)
C3A0.0161 (7)0.0207 (8)0.0184 (7)0.0037 (6)0.0093 (6)0.0043 (6)
C4A0.0143 (7)0.0184 (8)0.0170 (7)0.0009 (6)0.0057 (6)0.0037 (6)
C5A0.0125 (6)0.0124 (7)0.0148 (7)0.0001 (5)0.0043 (5)0.0031 (5)
C6A0.0162 (7)0.0208 (8)0.0175 (7)0.0009 (6)0.0042 (6)0.0022 (6)
C7A0.0231 (8)0.0201 (8)0.0168 (7)0.0006 (6)0.0079 (6)0.0029 (6)
C8A0.0192 (7)0.0142 (8)0.0213 (7)0.0002 (6)0.0107 (6)0.0010 (6)
C9A0.0147 (7)0.0110 (7)0.0164 (7)0.0015 (5)0.0062 (6)0.0033 (5)
C10A0.0135 (6)0.0145 (8)0.0137 (7)0.0013 (5)0.0047 (5)0.0034 (5)
C11A0.0140 (7)0.0173 (8)0.0207 (7)0.0031 (6)0.0053 (6)0.0059 (6)
C12A0.0134 (7)0.0200 (8)0.0218 (7)0.0004 (6)0.0053 (6)0.0043 (6)
C13A0.0113 (6)0.0166 (8)0.0181 (7)0.0017 (6)0.0047 (5)0.0019 (6)
C14A0.0169 (7)0.0181 (8)0.0175 (7)0.0031 (6)0.0044 (6)0.0040 (6)
C15A0.0162 (7)0.0100 (7)0.0199 (7)0.0016 (5)0.0087 (6)0.0014 (6)
C16A0.0176 (7)0.0196 (8)0.0209 (8)0.0040 (6)0.0066 (6)0.0010 (6)
C17A0.0254 (8)0.0198 (9)0.0273 (8)0.0002 (6)0.0157 (7)0.0030 (7)
C18A0.0158 (7)0.0236 (9)0.0195 (7)0.0038 (6)0.0059 (6)0.0041 (6)
C19A0.0181 (8)0.0240 (9)0.0280 (8)0.0022 (6)0.0099 (7)0.0024 (7)
C20A0.0176 (7)0.0176 (8)0.0232 (8)0.0017 (6)0.0084 (6)0.0074 (6)
O1B0.0161 (6)0.0401 (8)0.0234 (6)0.0063 (5)0.0022 (5)0.0069 (5)
O2B0.0221 (6)0.0311 (7)0.0198 (6)0.0061 (5)0.0038 (5)0.0052 (5)
O3B0.0196 (5)0.0117 (5)0.0148 (5)0.0036 (4)0.0082 (4)0.0023 (4)
O4B0.0219 (6)0.0144 (6)0.0291 (6)0.0032 (4)0.0100 (5)0.0008 (5)
O5B0.0203 (6)0.0184 (6)0.0230 (6)0.0025 (4)0.0041 (5)0.0043 (5)
O6B0.0293 (6)0.0187 (6)0.0240 (6)0.0057 (5)0.0145 (5)0.0026 (5)
C1B0.0194 (7)0.0243 (9)0.0145 (7)0.0006 (6)0.0058 (6)0.0006 (6)
C2B0.0205 (8)0.0259 (9)0.0151 (7)0.0033 (6)0.0026 (6)0.0003 (6)
C3B0.0137 (7)0.0234 (9)0.0190 (7)0.0022 (6)0.0025 (6)0.0052 (6)
C4B0.0152 (7)0.0213 (9)0.0194 (7)0.0012 (6)0.0058 (6)0.0022 (6)
C5B0.0141 (7)0.0150 (8)0.0149 (7)0.0007 (5)0.0042 (5)0.0014 (6)
C6B0.0200 (8)0.0182 (8)0.0184 (7)0.0023 (6)0.0074 (6)0.0013 (6)
C7B0.0197 (8)0.0149 (8)0.0181 (7)0.0009 (6)0.0033 (6)0.0037 (6)
C8B0.0177 (7)0.0124 (8)0.0224 (8)0.0003 (6)0.0055 (6)0.0010 (6)
C9B0.0178 (7)0.0106 (7)0.0161 (7)0.0014 (5)0.0060 (6)0.0037 (5)
C10B0.0171 (7)0.0156 (8)0.0147 (7)0.0014 (6)0.0058 (6)0.0034 (6)
C11B0.0180 (7)0.0198 (8)0.0195 (7)0.0014 (6)0.0086 (6)0.0060 (6)
C12B0.0198 (7)0.0196 (8)0.0180 (7)0.0032 (6)0.0095 (6)0.0045 (6)
C13B0.0180 (7)0.0159 (8)0.0146 (7)0.0043 (6)0.0072 (6)0.0014 (6)
C14B0.0208 (7)0.0148 (8)0.0150 (7)0.0024 (6)0.0058 (6)0.0011 (6)
C15B0.0202 (7)0.0087 (7)0.0201 (7)0.0002 (6)0.0064 (6)0.0011 (6)
C16B0.0233 (8)0.0175 (8)0.0183 (7)0.0038 (6)0.0074 (6)0.0008 (6)
C17B0.0187 (8)0.0184 (9)0.0314 (9)0.0021 (6)0.0070 (7)0.0018 (7)
C18B0.0178 (8)0.0327 (10)0.0209 (8)0.0018 (7)0.0082 (6)0.0013 (7)
C19B0.0197 (8)0.0285 (10)0.0321 (9)0.0067 (7)0.0079 (7)0.0048 (7)
C20B0.0223 (8)0.0228 (9)0.0227 (8)0.0040 (7)0.0079 (6)0.0093 (7)
O1C0.0141 (5)0.0246 (6)0.0193 (5)0.0040 (4)0.0075 (4)0.0012 (4)
O2C0.0155 (5)0.0235 (6)0.0175 (5)0.0022 (4)0.0050 (4)0.0037 (4)
O3C0.0111 (5)0.0129 (5)0.0160 (5)0.0012 (4)0.0047 (4)0.0019 (4)
O4C0.0211 (6)0.0192 (6)0.0294 (6)0.0057 (5)0.0122 (5)0.0024 (5)
O5C0.0170 (5)0.0185 (6)0.0206 (5)0.0018 (4)0.0084 (4)0.0042 (4)
O6C0.0138 (5)0.0223 (6)0.0284 (6)0.0038 (4)0.0079 (4)0.0068 (5)
C1C0.0119 (6)0.0184 (8)0.0143 (6)0.0005 (5)0.0031 (5)0.0014 (6)
C2C0.0165 (7)0.0212 (8)0.0137 (7)0.0017 (6)0.0053 (6)0.0013 (6)
C3C0.0113 (7)0.0163 (8)0.0145 (7)0.0007 (5)0.0055 (5)0.0008 (5)
C4C0.0126 (6)0.0127 (7)0.0174 (7)0.0020 (5)0.0052 (5)0.0018 (6)
C5C0.0146 (7)0.0114 (7)0.0145 (7)0.0006 (5)0.0053 (5)0.0003 (5)
C6C0.0182 (7)0.0153 (8)0.0271 (8)0.0037 (6)0.0092 (6)0.0060 (6)
C7C0.0233 (8)0.0189 (8)0.0254 (8)0.0015 (6)0.0113 (7)0.0093 (6)
C8C0.0195 (7)0.0119 (8)0.0258 (8)0.0030 (6)0.0112 (6)0.0008 (6)
C9C0.0157 (7)0.0117 (7)0.0147 (7)0.0017 (5)0.0060 (6)0.0031 (5)
C10C0.0133 (7)0.0146 (7)0.0148 (7)0.0017 (5)0.0055 (5)0.0025 (6)
C11C0.0120 (7)0.0217 (8)0.0183 (7)0.0032 (6)0.0042 (6)0.0042 (6)
C12C0.0125 (7)0.0219 (9)0.0196 (7)0.0011 (6)0.0050 (6)0.0009 (6)
C13C0.0119 (7)0.0147 (7)0.0166 (7)0.0017 (5)0.0061 (5)0.0005 (6)
C14C0.0170 (7)0.0165 (8)0.0175 (7)0.0025 (6)0.0088 (6)0.0020 (6)
C15C0.0155 (7)0.0171 (8)0.0174 (7)0.0024 (6)0.0095 (6)0.0000 (6)
C16C0.0162 (7)0.0179 (8)0.0207 (7)0.0029 (6)0.0086 (6)0.0041 (6)
C17C0.0240 (8)0.0169 (8)0.0374 (9)0.0044 (6)0.0177 (7)0.0035 (7)
C18C0.0142 (7)0.0175 (8)0.0177 (7)0.0033 (6)0.0049 (6)0.0009 (6)
C19C0.0209 (8)0.0194 (8)0.0265 (8)0.0017 (6)0.0123 (6)0.0060 (7)
C20C0.0188 (7)0.0213 (9)0.0220 (8)0.0040 (6)0.0079 (6)0.0082 (6)
O1D0.0121 (5)0.0282 (7)0.0202 (5)0.0022 (4)0.0060 (4)0.0016 (5)
O2D0.0174 (5)0.0199 (6)0.0164 (5)0.0004 (4)0.0060 (4)0.0039 (4)
O3D0.0122 (5)0.0119 (5)0.0151 (5)0.0034 (4)0.0059 (4)0.0023 (4)
O4D0.0202 (5)0.0139 (6)0.0277 (6)0.0007 (4)0.0112 (5)0.0006 (4)
O5D0.0187 (5)0.0171 (6)0.0266 (6)0.0025 (4)0.0108 (5)0.0082 (5)
O6D0.0176 (5)0.0190 (6)0.0356 (7)0.0010 (4)0.0146 (5)0.0066 (5)
C1D0.0138 (7)0.0197 (8)0.0156 (7)0.0004 (6)0.0067 (5)0.0018 (6)
C2D0.0146 (7)0.0209 (8)0.0137 (7)0.0000 (6)0.0035 (5)0.0012 (6)
C3D0.0113 (6)0.0165 (8)0.0164 (7)0.0000 (5)0.0044 (5)0.0003 (6)
C4D0.0131 (7)0.0135 (8)0.0154 (7)0.0029 (5)0.0055 (5)0.0011 (5)
C5D0.0137 (7)0.0120 (7)0.0137 (6)0.0013 (5)0.0054 (5)0.0011 (5)
C6D0.0201 (8)0.0170 (8)0.0246 (8)0.0003 (6)0.0086 (6)0.0059 (6)
C7D0.0214 (8)0.0166 (8)0.0265 (8)0.0030 (6)0.0078 (7)0.0080 (6)
C8D0.0176 (7)0.0122 (8)0.0284 (8)0.0018 (6)0.0079 (6)0.0013 (6)
C9D0.0143 (7)0.0119 (7)0.0172 (7)0.0016 (5)0.0060 (5)0.0040 (6)
C10D0.0133 (7)0.0138 (7)0.0148 (7)0.0016 (5)0.0059 (5)0.0039 (6)
C11D0.0150 (7)0.0218 (8)0.0202 (7)0.0021 (6)0.0095 (6)0.0058 (6)
C12D0.0142 (7)0.0231 (9)0.0202 (7)0.0011 (6)0.0090 (6)0.0033 (6)
C13D0.0127 (7)0.0145 (8)0.0163 (7)0.0019 (5)0.0066 (5)0.0008 (5)
C14D0.0150 (7)0.0153 (8)0.0162 (7)0.0007 (6)0.0044 (6)0.0002 (6)
C15D0.0115 (6)0.0165 (8)0.0157 (7)0.0006 (5)0.0025 (5)0.0014 (6)
C16D0.0152 (7)0.0173 (8)0.0166 (7)0.0012 (6)0.0061 (6)0.0022 (6)
C17D0.0188 (8)0.0160 (9)0.0427 (10)0.0051 (6)0.0100 (7)0.0056 (7)
C18D0.0174 (7)0.0189 (8)0.0172 (7)0.0026 (6)0.0083 (6)0.0006 (6)
C19D0.0174 (7)0.0185 (8)0.0228 (8)0.0074 (6)0.0072 (6)0.0056 (6)
C20D0.0168 (7)0.0234 (9)0.0230 (8)0.0045 (6)0.0076 (6)0.0111 (7)
O1E0.0407 (8)0.0422 (9)0.0264 (6)0.0101 (6)0.0142 (6)0.0045 (6)
N1E0.0281 (8)0.0276 (8)0.0239 (7)0.0012 (6)0.0081 (6)0.0020 (6)
C1E0.0261 (8)0.0292 (10)0.0242 (8)0.0043 (7)0.0091 (7)0.0023 (7)
C2E0.0278 (11)0.089 (2)0.0347 (11)0.0074 (12)0.0071 (9)0.0059 (12)
C3E0.0579 (14)0.0365 (12)0.0260 (10)0.0148 (10)0.0052 (9)0.0082 (9)
O1F0.0359 (8)0.0482 (9)0.0266 (7)0.0010 (6)0.0088 (6)0.0020 (6)
N1F0.0278 (8)0.0275 (9)0.0252 (7)0.0004 (6)0.0053 (6)0.0018 (6)
C1F0.0268 (9)0.0359 (11)0.0331 (10)0.0022 (8)0.0069 (8)0.0053 (8)
C2F0.0374 (11)0.0540 (15)0.0349 (11)0.0026 (10)0.0155 (9)0.0019 (10)
C3F0.0520 (13)0.0417 (13)0.0321 (10)0.0191 (10)0.0127 (10)0.0090 (9)
O1W0.0367 (8)0.0813 (14)0.0515 (10)0.0099 (8)0.0227 (8)0.0231 (9)
O2W0.0232 (6)0.0317 (7)0.0245 (6)0.0011 (5)0.0101 (5)0.0051 (5)
O3W0.0302 (7)0.0327 (8)0.0349 (7)0.0029 (5)0.0139 (6)0.0048 (6)
O4W0.0226 (6)0.0248 (7)0.0270 (6)0.0040 (5)0.0090 (5)0.0009 (5)
O5W0.0286 (7)0.0390 (9)0.0404 (8)0.0123 (6)0.0029 (6)0.0187 (7)
O6W0.0222 (6)0.0266 (7)0.0301 (6)0.0045 (5)0.0054 (5)0.0081 (5)
O7W0.0746 (12)0.0325 (8)0.0365 (8)0.0038 (7)0.0346 (8)0.0002 (6)
O8W0.0562 (10)0.0363 (9)0.0411 (9)0.0012 (8)0.0071 (8)0.0028 (7)
Geometric parameters (Å, º) top
Na1—O2B2.3488 (16)O3C—C9C1.4601 (17)
Na1—O1W2.3917 (18)O4C—C16C1.427 (2)
Na1—O2W2.4151 (16)O4C—H4OC0.8201
Na1—O3W2.5605 (16)O5C—C15C1.265 (2)
Na1—O5Bi2.6656 (14)O6C—C15C1.2616 (19)
Na1—O6Bi2.9399 (15)C1C—C2C1.531 (2)
Na1—H1W12.6504C1C—C10C1.538 (2)
Na2—O5A2.2860 (12)C1C—H1C10.9700
Na2—O5W2.3124 (16)C1C—H1C20.9699
Na2—O2Ai2.3841 (13)C2C—C3C1.517 (2)
Na2—O5D2.3928 (13)C2C—H2C10.9699
Na2—O3W2.4779 (15)C2C—H2C20.9698
Na2—O4W2.5377 (14)C3C—C4C1.547 (2)
Na2—H4W12.6402C3C—H3C0.9800
Na3—O5D2.3479 (12)C4C—C19C1.535 (2)
Na3—O5C2.3640 (12)C4C—C18C1.546 (2)
Na3—O5A2.4036 (13)C4C—C5C1.563 (2)
Na3—O4C2.5108 (14)C5C—C6C1.537 (2)
Na3—O4D2.5130 (13)C5C—C10C1.565 (2)
Na3—O5B2.5358 (14)C5C—H5C0.9799
Na4—O1F2.2610 (16)C6C—C7C1.526 (2)
Na4—O4Wii2.2782 (14)C6C—H6C10.9699
Na4—O6W2.3304 (15)C6C—H6C20.9700
Na4—O5C2.3856 (13)C7C—C8C1.521 (2)
Na4—O6C2.4619 (14)C7C—H7C10.9698
Na4—C15C2.7342 (18)C7C—H7C20.9699
O1A—C3A1.4311 (18)C8C—C17C1.531 (2)
O1A—H1A0.8200C8C—C9C1.551 (2)
O2A—C18A1.440 (2)C8C—H8C0.9800
O2A—Na2ii2.3841 (13)C9C—C11C1.540 (2)
O2A—H2OA0.8200C9C—C10C1.582 (2)
O3A—C13A1.4514 (18)C10C—C20C1.549 (2)
O3A—C9A1.4520 (18)C11C—C12C1.533 (2)
O4A—C16A1.423 (2)C11C—H11E0.9700
O4A—H4A0.8200C11C—H11F0.9700
O5A—C15A1.2518 (19)C12C—C13C1.537 (2)
O6A—C15A1.2633 (19)C12C—H12E0.9700
C1A—C2A1.532 (2)C12C—H12F0.9700
C1A—C10A1.535 (2)C13C—C16C1.530 (2)
C1A—H1A10.9699C13C—C14C1.535 (2)
C1A—H1A20.9702C14C—C15C1.520 (2)
C2A—C3A1.509 (2)C14C—H14E0.9699
C2A—H2A10.9700C14C—H14F0.9699
C2A—H2A20.9699C16C—H16E0.9698
C3A—C4A1.539 (2)C16C—H16F0.9701
C3A—H3A0.9797C17C—H17G0.9599
C4A—C19A1.537 (2)C17C—H17H0.9601
C4A—C18A1.553 (2)C17C—H17I0.9595
C4A—C5A1.562 (2)C18C—H18E0.9700
C5A—C6A1.525 (2)C18C—H18F0.9698
C5A—C10A1.568 (2)C19C—H19G0.9600
C5A—H5A0.9801C19C—H19H0.9599
C6A—C7A1.528 (2)C19C—H19I0.9602
C6A—H6A10.9700C20C—H20G0.9600
C6A—H6A20.9701C20C—H20H0.9597
C7A—C8A1.530 (2)C20C—H20I0.9599
C7A—H7A10.9699O1D—C3D1.4366 (17)
C7A—H7A20.9701O1D—H1D0.8200
C8A—C17A1.531 (2)O2D—C18D1.435 (2)
C8A—C9A1.555 (2)O2D—H2OD0.8200
C8A—H8A0.9799O3D—C13D1.4493 (17)
C9A—C11A1.540 (2)O3D—C9D1.4573 (18)
C9A—C10A1.580 (2)O4D—C16D1.4175 (19)
C10A—C20A1.542 (2)O4D—H4OD0.8199
C11A—C12A1.537 (2)O5D—C15D1.244 (2)
C11A—H11A0.9700O6D—C15D1.2810 (19)
C11A—H11B0.9701C1D—C2D1.526 (2)
C12A—C13A1.530 (2)C1D—C10D1.544 (2)
C12A—H12A0.9703C1D—H1D10.9701
C12A—H12B0.9700C1D—H1D20.9699
C13A—C14A1.521 (2)C2D—C3D1.512 (2)
C13A—C16A1.528 (2)C2D—H2D10.9698
C14A—C15A1.521 (2)C2D—H2D20.9703
C14A—H14A0.9701C3D—C4D1.546 (2)
C14A—H14B0.9700C3D—H3D0.9800
C16A—H16A0.9701C4D—C19D1.541 (2)
C16A—H16B0.9701C4D—C18D1.542 (2)
C17A—H17A0.9601C4D—C5D1.565 (2)
C17A—H17B0.9599C5D—C6D1.537 (2)
C17A—H17C0.9601C5D—C10D1.566 (2)
C18A—H18A0.9699C5D—H5D0.9799
C18A—H18B0.9699C6D—C7D1.525 (2)
C19A—H19A0.9601C6D—H6D10.9698
C19A—H19B0.9602C6D—H6D20.9700
C19A—H19C0.9600C7D—C8D1.529 (2)
C20A—H20A0.9600C7D—H7D10.9699
C20A—H20B0.9600C7D—H7D20.9700
C20A—H20C0.9600C8D—C17D1.530 (2)
O1B—C3B1.4399 (19)C8D—C9D1.552 (2)
O1B—H1B0.8200C8D—H8D0.9795
O2B—C18B1.423 (2)C9D—C11D1.543 (2)
O2B—H2OB0.8200C9D—C10D1.577 (2)
O3B—C9B1.4523 (18)C10D—C20D1.544 (2)
O3B—C13B1.4544 (18)C11D—C12D1.534 (2)
O4B—C16B1.428 (2)C11D—H11G0.9699
O4B—H4B0.8200C11D—H11H0.9700
O5B—C15B1.262 (2)C12D—C13D1.532 (2)
O5B—Na1ii2.6656 (14)C12D—H12G0.9702
O6B—C15B1.267 (2)C12D—H12H0.9699
O6B—Na1ii2.9399 (15)C13D—C16D1.527 (2)
C1B—C2B1.529 (2)C13D—C14D1.534 (2)
C1B—C10B1.539 (2)C14D—C15D1.519 (2)
C1B—H1B10.9700C14D—H14G0.9698
C1B—H1B20.9696C14D—H14H0.9701
C2B—C3B1.515 (2)C16D—H16G0.9700
C2B—H2B10.9700C16D—H16H0.9701
C2B—H2B20.9700C17D—H17J0.9596
C3B—C4B1.536 (2)C17D—H17K0.9600
C3B—H3B0.9800C17D—H17L0.9599
C4B—C18B1.539 (2)C18D—H18G0.9699
C4B—C19B1.542 (2)C18D—H18H0.9700
C4B—C5B1.568 (2)C19D—H19J0.9600
C5B—C6B1.530 (2)C19D—H19K0.9601
C5B—C10B1.563 (2)C19D—H19L0.9601
C5B—H5B0.9800C20D—H20J0.9599
C6B—C7B1.526 (2)C20D—H20K0.9607
C6B—H6B10.9700C20D—H20L0.9600
C6B—H6B20.9700O1E—C1E1.218 (2)
C7B—C8B1.525 (2)N1E—C1E1.327 (2)
C7B—H7B10.9702N1E—C2E1.443 (3)
C7B—H7B20.9702N1E—C3E1.450 (3)
C8B—C17B1.532 (2)C1E—H1E0.9300
C8B—C9B1.553 (2)C2E—H2E10.9599
C8B—H8B0.9800C2E—H2E20.9599
C9B—C11B1.539 (2)C2E—H2E30.9599
C9B—C10B1.586 (2)C3E—H3E10.9599
C10B—C20B1.545 (2)C3E—H3E20.9600
C11B—C12B1.533 (2)C3E—H3E30.9600
C11B—H11C0.9700O1F—C1F1.220 (3)
C11B—H11D0.9701N1F—C1F1.318 (3)
C12B—C13B1.534 (2)N1F—C3F1.446 (3)
C12B—H12C0.9699N1F—C2F1.458 (3)
C12B—H12D0.9699C1F—H1F0.9300
C13B—C16B1.524 (2)C2F—H2F10.9601
C13B—C14B1.531 (2)C2F—H2F20.9600
C14B—C15B1.531 (2)C2F—H2F30.9601
C14B—H14C0.9699C3F—H3F10.9600
C14B—H14D0.9700C3F—H3F20.9602
C16B—H16C0.9701C3F—H3F30.9598
C16B—H16D0.9697O1W—H1W10.8500
C17B—H17D0.9600O1W—H1W20.8498
C17B—H17E0.9600O2W—H2W10.8501
C17B—H17F0.9601O2W—H2W20.8493
C18B—H18C0.9701O3W—H3W10.8499
C18B—H18D0.9699O3W—H3W20.8500
C19B—H19D0.9600O4W—Na4i2.2782 (14)
C19B—H19E0.9600O4W—H4W10.8501
C19B—H19F0.9600O4W—H4W20.8499
C20B—H20D0.9600O5W—H5W10.8500
C20B—H20E0.9600O5W—H5W20.8500
C20B—H20F0.9600O6W—H6W10.8500
O1C—C3C1.4324 (17)O6W—H6W20.8498
O1C—H1C0.8200O7W—H7W10.8501
O2C—C18C1.433 (2)O7W—H7W20.8501
O2C—H2OC0.8198O8W—H8W10.8499
O3C—C13C1.4434 (17)O8W—H8W20.8499
O2B—Na1—O1W116.29 (7)O4B—C16B—C13B112.62 (13)
O2B—Na1—O2W157.25 (5)O4B—C16B—H16C109.0
O1W—Na1—O2W85.61 (7)C13B—C16B—H16C109.1
O2B—Na1—O3W82.25 (5)O4B—C16B—H16D109.2
O1W—Na1—O3W75.54 (6)C13B—C16B—H16D109.1
O2W—Na1—O3W98.53 (5)H16C—C16B—H16D107.8
O2B—Na1—O5Bi82.13 (5)C8B—C17B—H17D109.5
O1W—Na1—O5Bi131.15 (6)C8B—C17B—H17E109.5
O2W—Na1—O5Bi87.80 (5)H17D—C17B—H17E109.5
O3W—Na1—O5Bi153.17 (6)C8B—C17B—H17F109.4
O2B—Na1—O6Bi83.48 (5)H17D—C17B—H17F109.5
O1W—Na1—O6Bi88.81 (6)H17E—C17B—H17F109.5
O2W—Na1—O6Bi104.17 (5)O2B—C18B—C4B113.87 (14)
O3W—Na1—O6Bi151.30 (5)O2B—C18B—H18C108.7
O5Bi—Na1—O6Bi46.47 (4)C4B—C18B—H18C108.8
O2B—Na1—Na4i96.53 (4)O2B—C18B—H18D108.8
O1W—Na1—Na4i139.39 (6)C4B—C18B—H18D108.8
O2W—Na1—Na4i60.95 (3)H18C—C18B—H18D107.7
O3W—Na1—Na4i86.69 (4)C4B—C19B—H19D109.5
O5Bi—Na1—Na4i73.60 (3)C4B—C19B—H19E109.5
O6Bi—Na1—Na4i119.66 (3)H19D—C19B—H19E109.5
O2B—Na1—Na2110.02 (4)C4B—C19B—H19F109.4
O1W—Na1—Na279.94 (5)H19D—C19B—H19F109.5
O2W—Na1—Na265.73 (4)H19E—C19B—H19F109.5
O3W—Na1—Na233.38 (4)C10B—C20B—H20D109.5
O5Bi—Na1—Na2138.80 (4)C10B—C20B—H20E109.5
O6Bi—Na1—Na2165.25 (4)H20D—C20B—H20E109.5
Na4i—Na1—Na266.112 (18)C10B—C20B—H20F109.5
O2B—Na1—H1W1129.3H20D—C20B—H20F109.5
O1W—Na1—H1W118.5H20E—C20B—H20F109.5
O2W—Na1—H1W173.4C3C—O1C—H1C109.5
O3W—Na1—H1W191.3C18C—O2C—H2OC104.0
O5Bi—Na1—H1W1115.4C13C—O3C—C9C113.01 (11)
O6Bi—Na1—H1W178.8C16C—O4C—Na3127.68 (9)
Na4i—Na1—H1W1133.4C16C—O4C—H4OC110.0
Na2—Na1—H1W187.8Na3—O4C—H4OC113.5
O5A—Na2—O5W94.70 (6)C15C—O5C—Na3125.87 (9)
O5A—Na2—O2Ai93.46 (5)C15C—O5C—Na491.75 (9)
O5W—Na2—O2Ai83.27 (6)Na3—O5C—Na4114.05 (5)
O5A—Na2—O5D79.69 (4)C15C—O6C—Na488.37 (10)
O5W—Na2—O5D100.23 (5)C2C—C1C—C10C113.15 (13)
O2Ai—Na2—O5D172.50 (5)C2C—C1C—H1C1108.9
O5A—Na2—O3W104.75 (5)C10C—C1C—H1C1108.9
O5W—Na2—O3W160.54 (6)C2C—C1C—H1C2109.0
O2Ai—Na2—O3W94.69 (5)C10C—C1C—H1C2109.0
O5D—Na2—O3W84.20 (5)H1C1—C1C—H1C2107.8
O5A—Na2—O4W153.17 (5)C3C—C2C—C1C109.57 (12)
O5W—Na2—O4W77.64 (6)C3C—C2C—H2C1109.8
O2Ai—Na2—O4W110.82 (5)C1C—C2C—H2C1109.8
O5D—Na2—O4W76.52 (4)C3C—C2C—H2C2109.7
O3W—Na2—O4W85.10 (5)C1C—C2C—H2C2109.7
O5A—Na2—Na343.39 (3)H2C1—C2C—H2C2108.2
O5W—Na2—Na382.63 (4)O1C—C3C—C2C108.06 (12)
O2Ai—Na2—Na3132.68 (4)O1C—C3C—C4C111.59 (12)
O5D—Na2—Na342.26 (3)C2C—C3C—C4C113.34 (12)
O3W—Na2—Na3112.03 (4)O1C—C3C—H3C107.9
O4W—Na2—Na3109.79 (4)C2C—C3C—H3C107.9
O5A—Na2—Na1130.03 (4)C4C—C3C—H3C107.9
O5W—Na2—Na1128.47 (4)C19C—C4C—C18C105.07 (12)
O2Ai—Na2—Na171.50 (4)C19C—C4C—C3C111.72 (13)
O5D—Na2—Na1110.57 (4)C18C—C4C—C3C106.91 (12)
O3W—Na2—Na134.64 (4)C19C—C4C—C5C113.77 (13)
O4W—Na2—Na171.04 (3)C18C—C4C—C5C109.78 (12)
Na3—Na2—Na1146.23 (2)C3C—C4C—C5C109.30 (12)
O5A—Na2—H4W1140.2C6C—C5C—C4C113.34 (12)
O5W—Na2—H4W190.9C6C—C5C—C10C111.45 (13)
O2Ai—Na2—H4W1126.3C4C—C5C—C10C115.86 (12)
O5D—Na2—H4W160.6C6C—C5C—H5C105.0
O3W—Na2—H4W174.7C4C—C5C—H5C105.0
O4W—Na2—H4W118.8C10C—C5C—H5C105.0
Na3—Na2—H4W198.9C7C—C6C—C5C110.77 (13)
Na1—Na2—H4W171.3C7C—C6C—H6C1109.6
O5D—Na3—O5C164.27 (5)C5C—C6C—H6C1109.5
O5D—Na3—O5A78.26 (4)C7C—C6C—H6C2109.4
O5C—Na3—O5A111.68 (5)C5C—C6C—H6C2109.4
O5D—Na3—O4C80.55 (4)H6C1—C6C—H6C2108.0
O5C—Na3—O4C85.01 (4)C8C—C7C—C6C111.83 (14)
O5A—Na3—O4C104.64 (5)C8C—C7C—H7C1109.2
O5D—Na3—O4D84.89 (4)C6C—C7C—H7C1109.1
O5C—Na3—O4D86.28 (4)C8C—C7C—H7C2109.3
O5A—Na3—O4D161.79 (5)C6C—C7C—H7C2109.4
O4C—Na3—O4D79.06 (4)H7C1—C7C—H7C2107.9
O5D—Na3—O5B109.59 (5)C7C—C8C—C17C109.93 (14)
O5C—Na3—O5B83.96 (4)C7C—C8C—C9C110.62 (13)
O5A—Na3—O5B85.54 (4)C17C—C8C—C9C115.03 (14)
O4C—Na3—O5B167.18 (5)C7C—C8C—H8C106.9
O4D—Na3—O5B93.72 (4)C17C—C8C—H8C106.9
O5D—Na3—Na243.26 (3)C9C—C8C—H8C106.9
O5C—Na3—Na2138.77 (4)O3C—C9C—C11C104.39 (12)
O5A—Na3—Na240.80 (3)O3C—C9C—C8C109.05 (12)
O4C—Na3—Na277.93 (3)C11C—C9C—C8C111.91 (13)
O4D—Na3—Na2125.79 (3)O3C—C9C—C10C108.12 (11)
O5B—Na3—Na2114.79 (3)C11C—C9C—C10C113.49 (12)
O5D—Na3—Na4140.32 (4)C8C—C9C—C10C109.61 (12)
O5C—Na3—Na433.14 (3)C1C—C10C—C20C108.96 (13)
O5A—Na3—Na4141.00 (4)C1C—C10C—C5C107.62 (12)
O4C—Na3—Na490.79 (3)C20C—C10C—C5C113.87 (13)
O4D—Na3—Na455.42 (3)C1C—C10C—C9C110.60 (12)
O5B—Na3—Na476.40 (3)C20C—C10C—C9C107.60 (12)
Na2—Na3—Na4167.64 (2)C5C—C10C—C9C108.20 (11)
O1F—Na4—O4Wii101.38 (6)C12C—C11C—C9C105.59 (12)
O1F—Na4—O6W107.39 (6)C12C—C11C—H11E110.6
O4Wii—Na4—O6W98.72 (5)C9C—C11C—H11E110.6
O1F—Na4—O5C126.57 (6)C12C—C11C—H11F110.6
O4Wii—Na4—O5C126.42 (5)C9C—C11C—H11F110.6
O6W—Na4—O5C89.20 (5)H11E—C11C—H11F108.8
O1F—Na4—O6C96.06 (6)C11C—C12C—C13C104.37 (12)
O4Wii—Na4—O6C103.66 (5)C11C—C12C—H12E110.9
O6W—Na4—O6C143.52 (5)C13C—C12C—H12E110.9
O5C—Na4—O6C54.33 (4)C11C—C12C—H12F110.9
O1F—Na4—C15C109.49 (6)C13C—C12C—H12F110.9
O4Wii—Na4—C15C121.81 (5)H12E—C12C—H12F108.9
O6W—Na4—C15C116.27 (5)O3C—C13C—C16C109.49 (12)
O5C—Na4—C15C27.55 (4)O3C—C13C—C14C106.17 (12)
O6C—Na4—C15C27.47 (4)C16C—C13C—C14C109.72 (13)
O1F—Na4—Na3111.73 (5)O3C—C13C—C12C106.04 (12)
O4Wii—Na4—Na3145.87 (4)C16C—C13C—C12C109.70 (13)
O6W—Na4—Na364.23 (4)C14C—C13C—C12C115.50 (13)
O5C—Na4—Na332.81 (3)C15C—C14C—C13C114.48 (13)
O6C—Na4—Na381.42 (3)C15C—C14C—H14E108.6
C15C—Na4—Na354.48 (4)C13C—C14C—H14E108.6
O1F—Na4—Na1ii152.55 (5)C15C—C14C—H14F108.6
O4Wii—Na4—Na1ii75.09 (4)C13C—C14C—H14F108.6
O6W—Na4—Na1ii48.03 (4)H14E—C14C—H14F107.6
O5C—Na4—Na1ii71.82 (3)O6C—C15C—O5C122.38 (14)
O6C—Na4—Na1ii111.30 (4)O6C—C15C—C14C119.35 (14)
C15C—Na4—Na1ii94.72 (4)O5C—C15C—C14C118.27 (13)
C3A—O1A—H1A109.5O6C—C15C—Na464.17 (9)
C18A—O2A—Na2ii121.82 (10)O5C—C15C—Na460.70 (8)
C18A—O2A—H2OA108.3C14C—C15C—Na4163.80 (10)
Na2ii—O2A—H2OA107.0O4C—C16C—C13C110.55 (13)
C13A—O3A—C9A113.10 (11)O4C—C16C—H16E109.6
C16A—O4A—H4A109.5C13C—C16C—H16E109.5
C15A—O5A—Na2133.08 (10)O4C—C16C—H16F109.5
C15A—O5A—Na3130.01 (10)C13C—C16C—H16F109.5
Na2—O5A—Na395.81 (4)H16E—C16C—H16F108.1
C2A—C1A—C10A112.65 (13)C8C—C17C—H17G109.5
C2A—C1A—H1A1109.0C8C—C17C—H17H109.4
C10A—C1A—H1A1109.1H17G—C17C—H17H109.5
C2A—C1A—H1A2109.0C8C—C17C—H17I109.6
C10A—C1A—H1A2109.1H17G—C17C—H17I109.4
H1A1—C1A—H1A2107.8H17H—C17C—H17I109.5
C3A—C2A—C1A110.37 (13)O2C—C18C—C4C114.07 (12)
C3A—C2A—H2A1109.5O2C—C18C—H18E108.7
C1A—C2A—H2A1109.6C4C—C18C—H18E108.7
C3A—C2A—H2A2109.6O2C—C18C—H18F108.8
C1A—C2A—H2A2109.6C4C—C18C—H18F108.8
H2A1—C2A—H2A2108.1H18E—C18C—H18F107.6
O1A—C3A—C2A107.55 (12)C4C—C19C—H19G109.5
O1A—C3A—C4A112.45 (13)C4C—C19C—H19H109.5
C2A—C3A—C4A112.87 (13)H19G—C19C—H19H109.5
O1A—C3A—H3A107.9C4C—C19C—H19I109.5
C2A—C3A—H3A107.9H19G—C19C—H19I109.5
C4A—C3A—H3A107.9H19H—C19C—H19I109.5
C19A—C4A—C3A111.45 (13)C10C—C20C—H20G109.5
C19A—C4A—C18A106.46 (13)C10C—C20C—H20H109.5
C3A—C4A—C18A107.13 (13)H20G—C20C—H20H109.5
C19A—C4A—C5A113.20 (13)C10C—C20C—H20I109.4
C3A—C4A—C5A110.16 (12)H20G—C20C—H20I109.5
C18A—C4A—C5A108.14 (12)H20H—C20C—H20I109.5
C6A—C5A—C4A113.29 (12)C3D—O1D—H1D109.5
C6A—C5A—C10A111.08 (12)C18D—O2D—H2OD107.3
C4A—C5A—C10A117.47 (12)C13D—O3D—C9D112.96 (11)
C6A—C5A—H5A104.5C16D—O4D—Na3122.05 (9)
C4A—C5A—H5A104.5C16D—O4D—H4OD108.7
C10A—C5A—H5A104.5Na3—O4D—H4OD111.2
C5A—C6A—C7A110.49 (13)C15D—O5D—Na3131.29 (10)
C5A—C6A—H6A1110.2C15D—O5D—Na2133.64 (10)
C7A—C6A—H6A1110.2Na3—O5D—Na294.48 (5)
C5A—C6A—H6A2111.1C2D—C1D—C10D113.46 (13)
C7A—C6A—H6A2111.1C2D—C1D—H1D1108.9
H6A1—C6A—H6A2103.6C10D—C1D—H1D1108.9
C6A—C7A—C8A112.40 (13)C2D—C1D—H1D2108.9
C6A—C7A—H7A1109.1C10D—C1D—H1D2108.9
C8A—C7A—H7A1109.1H1D1—C1D—H1D2107.7
C6A—C7A—H7A2109.1C3D—C2D—C1D110.22 (12)
C8A—C7A—H7A2109.1C3D—C2D—H2D1109.6
H7A1—C7A—H7A2107.9C1D—C2D—H2D1109.6
C7A—C8A—C17A109.48 (13)C3D—C2D—H2D2109.6
C7A—C8A—C9A110.53 (13)C1D—C2D—H2D2109.6
C17A—C8A—C9A116.18 (13)H2D1—C2D—H2D2108.1
C7A—C8A—H8A106.7O1D—C3D—C2D108.32 (12)
C17A—C8A—H8A106.7O1D—C3D—C4D112.24 (12)
C9A—C8A—H8A106.7C2D—C3D—C4D112.48 (13)
O3A—C9A—C11A104.20 (12)O1D—C3D—H3D107.9
O3A—C9A—C8A109.39 (12)C2D—C3D—H3D107.9
C11A—C9A—C8A111.52 (12)C4D—C3D—H3D107.9
O3A—C9A—C10A107.31 (11)C19D—C4D—C18D104.22 (12)
C11A—C9A—C10A114.57 (12)C19D—C4D—C3D111.32 (12)
C8A—C9A—C10A109.54 (12)C18D—C4D—C3D108.03 (12)
C1A—C10A—C20A108.06 (12)C19D—C4D—C5D113.86 (13)
C1A—C10A—C5A108.33 (12)C18D—C4D—C5D110.26 (12)
C20A—C10A—C5A114.56 (13)C3D—C4D—C5D108.93 (12)
C1A—C10A—C9A110.55 (12)C6D—C5D—C4D113.61 (12)
C20A—C10A—C9A109.13 (12)C6D—C5D—C10D111.17 (12)
C5A—C10A—C9A106.20 (11)C4D—C5D—C10D115.70 (12)
C12A—C11A—C9A105.19 (12)C6D—C5D—H5D105.0
C12A—C11A—H11A110.7C4D—C5D—H5D105.1
C9A—C11A—H11A110.7C10D—C5D—H5D105.0
C12A—C11A—H11B110.7C7D—C6D—C5D111.09 (13)
C9A—C11A—H11B110.7C7D—C6D—H6D1109.4
H11A—C11A—H11B108.8C5D—C6D—H6D1109.4
C13A—C12A—C11A103.93 (12)C7D—C6D—H6D2109.5
C13A—C12A—H12A110.9C5D—C6D—H6D2109.5
C11A—C12A—H12A111.1H6D1—C6D—H6D2108.0
C13A—C12A—H12B110.9C6D—C7D—C8D112.15 (14)
C11A—C12A—H12B110.9C6D—C7D—H7D1109.2
H12A—C12A—H12B109.0C8D—C7D—H7D1109.1
O3A—C13A—C14A104.02 (12)C6D—C7D—H7D2109.2
O3A—C13A—C16A109.50 (12)C8D—C7D—H7D2109.2
C14A—C13A—C16A111.72 (14)H7D1—C7D—H7D2107.9
O3A—C13A—C12A105.54 (12)C7D—C8D—C17D109.96 (14)
C14A—C13A—C12A116.73 (13)C7D—C8D—C9D110.50 (13)
C16A—C13A—C12A108.88 (13)C17D—C8D—C9D115.00 (14)
C15A—C14A—C13A119.75 (13)C7D—C8D—H8D107.0
C15A—C14A—H14A107.4C17D—C8D—H8D107.0
C13A—C14A—H14A107.4C9D—C8D—H8D107.0
C15A—C14A—H14B107.4O3D—C9D—C11D104.50 (12)
C13A—C14A—H14B107.3O3D—C9D—C8D108.72 (12)
H14A—C14A—H14B106.9C11D—C9D—C8D111.83 (13)
O5A—C15A—O6A124.99 (14)O3D—C9D—C10D108.22 (11)
O5A—C15A—C14A115.33 (13)C11D—C9D—C10D114.12 (12)
O6A—C15A—C14A119.68 (13)C8D—C9D—C10D109.17 (12)
O4A—C16A—C13A112.94 (13)C1D—C10D—C20D108.00 (13)
O4A—C16A—H16A109.1C1D—C10D—C5D107.86 (12)
C13A—C16A—H16A109.1C20D—C10D—C5D114.09 (13)
O4A—C16A—H16B108.9C1D—C10D—C9D110.64 (12)
C13A—C16A—H16B108.9C20D—C10D—C9D107.63 (12)
H16A—C16A—H16B107.8C5D—C10D—C9D108.62 (11)
C8A—C17A—H17A109.4C12D—C11D—C9D105.32 (12)
C8A—C17A—H17B109.5C12D—C11D—H11G110.6
H17A—C17A—H17B109.5C9D—C11D—H11G110.6
C8A—C17A—H17C109.5C12D—C11D—H11H110.8
H17A—C17A—H17C109.5C9D—C11D—H11H110.7
H17B—C17A—H17C109.4H11G—C11D—H11H108.8
O2A—C18A—C4A113.99 (13)C13D—C12D—C11D104.48 (12)
O2A—C18A—H18A108.8C13D—C12D—H12G110.8
C4A—C18A—H18A108.8C11D—C12D—H12G110.9
O2A—C18A—H18B108.7C13D—C12D—H12H110.9
C4A—C18A—H18B108.7C11D—C12D—H12H110.8
H18A—C18A—H18B107.6H12G—C12D—H12H108.9
C4A—C19A—H19A109.5O3D—C13D—C16D108.43 (12)
C4A—C19A—H19B109.5O3D—C13D—C12D105.80 (12)
H19A—C19A—H19B109.4C16D—C13D—C12D109.94 (13)
C4A—C19A—H19C109.5O3D—C13D—C14D105.55 (11)
H19A—C19A—H19C109.5C16D—C13D—C14D110.59 (13)
H19B—C19A—H19C109.5C12D—C13D—C14D116.08 (13)
C10A—C20A—H20A109.5C15D—C14D—C13D115.30 (13)
C10A—C20A—H20B109.4C15D—C14D—H14G108.4
H20A—C20A—H20B109.5C13D—C14D—H14G108.4
C10A—C20A—H20C109.5C15D—C14D—H14H108.5
H20A—C20A—H20C109.5C13D—C14D—H14H108.5
H20B—C20A—H20C109.5H14G—C14D—H14H107.5
C3B—O1B—H1B109.5O5D—C15D—O6D123.45 (14)
C18B—O2B—Na1133.96 (11)O5D—C15D—C14D118.19 (13)
C18B—O2B—H2OB110.1O6D—C15D—C14D118.36 (14)
Na1—O2B—H2OB113.8O4D—C16D—C13D113.30 (12)
C9B—O3B—C13B112.84 (11)O4D—C16D—H16G108.9
C16B—O4B—H4B109.5C13D—C16D—H16G108.9
C15B—O5B—Na3122.63 (10)O4D—C16D—H16H109.0
C15B—O5B—Na1ii100.36 (10)C13D—C16D—H16H108.9
Na3—O5B—Na1ii130.33 (5)H16G—C16D—H16H107.7
C15B—O6B—Na1ii87.37 (10)C8D—C17D—H17J109.4
C2B—C1B—C10B113.17 (14)C8D—C17D—H17K109.5
C2B—C1B—H1B1109.0H17J—C17D—H17K109.5
C10B—C1B—H1B1109.0C8D—C17D—H17L109.5
C2B—C1B—H1B2108.9H17J—C17D—H17L109.5
C10B—C1B—H1B2108.9H17K—C17D—H17L109.5
H1B1—C1B—H1B2107.8O2D—C18D—C4D114.52 (12)
C3B—C2B—C1B110.59 (13)O2D—C18D—H18G108.6
C3B—C2B—H2B1109.5C4D—C18D—H18G108.6
C1B—C2B—H2B1109.5O2D—C18D—H18H108.7
C3B—C2B—H2B2109.6C4D—C18D—H18H108.6
C1B—C2B—H2B2109.5H18G—C18D—H18H107.6
H2B1—C2B—H2B2108.1C4D—C19D—H19J109.4
O1B—C3B—C2B107.93 (13)C4D—C19D—H19K109.5
O1B—C3B—C4B111.81 (14)H19J—C19D—H19K109.5
C2B—C3B—C4B112.81 (13)C4D—C19D—H19L109.5
O1B—C3B—H3B108.0H19J—C19D—H19L109.5
C2B—C3B—H3B108.0H19K—C19D—H19L109.5
C4B—C3B—H3B108.0C10D—C20D—H20J109.5
C3B—C4B—C18B108.23 (14)C10D—C20D—H20K109.5
C3B—C4B—C19B111.42 (14)H20J—C20D—H20K109.5
C18B—C4B—C19B104.63 (14)C10D—C20D—H20L109.5
C3B—C4B—C5B108.06 (13)H20J—C20D—H20L109.5
C18B—C4B—C5B109.39 (13)H20K—C20D—H20L109.5
C19B—C4B—C5B114.89 (14)C1E—N1E—C2E120.43 (18)
C6B—C5B—C10B111.71 (13)C1E—N1E—C3E121.65 (17)
C6B—C5B—C4B113.11 (13)C2E—N1E—C3E117.86 (18)
C10B—C5B—C4B115.88 (12)O1E—C1E—N1E125.55 (18)
C6B—C5B—H5B104.9O1E—C1E—H1E117.2
C10B—C5B—H5B105.0N1E—C1E—H1E117.2
C4B—C5B—H5B105.0N1E—C2E—H2E1109.3
C7B—C6B—C5B110.57 (13)N1E—C2E—H2E2109.6
C7B—C6B—H6B1109.5H2E1—C2E—H2E2109.4
C5B—C6B—H6B1109.5N1E—C2E—H2E3109.6
C7B—C6B—H6B2109.6H2E1—C2E—H2E3109.5
C5B—C6B—H6B2109.5H2E2—C2E—H2E3109.5
H6B1—C6B—H6B2108.1N1E—C3E—H3E1109.4
C8B—C7B—C6B111.30 (13)N1E—C3E—H3E2109.7
C8B—C7B—H7B1109.4H3E1—C3E—H3E2109.5
C6B—C7B—H7B1109.4N1E—C3E—H3E3109.3
C8B—C7B—H7B2109.4H3E1—C3E—H3E3109.5
C6B—C7B—H7B2109.4H3E2—C3E—H3E3109.5
H7B1—C7B—H7B2108.0C1F—O1F—Na4129.28 (14)
C7B—C8B—C17B110.18 (13)C1F—N1F—C3F121.89 (18)
C7B—C8B—C9B110.06 (13)C1F—N1F—C2F121.39 (18)
C17B—C8B—C9B115.58 (14)C3F—N1F—C2F116.67 (17)
C7B—C8B—H8B106.9O1F—C1F—N1F126.19 (19)
C17B—C8B—H8B106.9O1F—C1F—H1F116.9
C9B—C8B—H8B106.9N1F—C1F—H1F116.9
O3B—C9B—C11B104.96 (12)N1F—C2F—H2F1109.5
O3B—C9B—C8B107.96 (12)N1F—C2F—H2F2109.4
C11B—C9B—C8B111.98 (13)H2F1—C2F—H2F2109.5
O3B—C9B—C10B109.16 (12)N1F—C2F—H2F3109.5
C11B—C9B—C10B112.97 (12)H2F1—C2F—H2F3109.5
C8B—C9B—C10B109.57 (12)H2F2—C2F—H2F3109.4
C1B—C10B—C20B109.29 (13)N1F—C3F—H3F1109.5
C1B—C10B—C5B107.11 (12)N1F—C3F—H3F2109.4
C20B—C10B—C5B113.99 (13)H3F1—C3F—H3F2109.5
C1B—C10B—C9B109.93 (13)N1F—C3F—H3F3109.4
C20B—C10B—C9B108.26 (12)H3F1—C3F—H3F3109.5
C5B—C10B—C9B108.23 (12)H3F2—C3F—H3F3109.5
C12B—C11B—C9B105.23 (12)Na1—O1W—H1W198.2
C12B—C11B—H11C110.7Na1—O1W—H1W2111.7
C9B—C11B—H11C110.8H1W1—O1W—H1W2104.4
C12B—C11B—H11D110.6Na1—O2W—H2W1113.0
C9B—C11B—H11D110.6Na1—O2W—H2W2101.3
H11C—C11B—H11D108.8H2W1—O2W—H2W2104.5
C11B—C12B—C13B104.41 (12)Na2—O3W—Na1111.98 (6)
C11B—C12B—H12C110.9Na2—O3W—H3W198.1
C13B—C12B—H12C110.8Na1—O3W—H3W1116.5
C11B—C12B—H12D110.9Na2—O3W—H3W2102.9
C13B—C12B—H12D110.8Na1—O3W—H3W2120.0
H12C—C12B—H12D108.9H3W1—O3W—H3W2104.4
O3B—C13B—C16B108.96 (12)Na4i—O4W—Na2138.21 (6)
O3B—C13B—C14B105.84 (11)Na4i—O4W—H4W1114.0
C16B—C13B—C14B111.91 (13)Na2—O4W—H4W187.5
O3B—C13B—C12B105.27 (12)Na4i—O4W—H4W2104.3
C16B—C13B—C12B109.77 (13)Na2—O4W—H4W2104.1
C14B—C13B—C12B114.67 (13)H4W1—O4W—H4W2104.4
C15B—C14B—C13B120.00 (13)Na2—O5W—H5W1130.4
C15B—C14B—H14C107.3Na2—O5W—H5W2123.3
C13B—C14B—H14C107.4H5W1—O5W—H5W2104.4
C15B—C14B—H14D107.3Na4—O6W—H6W1127.0
C13B—C14B—H14D107.3Na4—O6W—H6W2125.0
H14C—C14B—H14D106.9H6W1—O6W—H6W2104.4
O5B—C15B—O6B123.34 (15)H7W1—O7W—H7W2104.4
O5B—C15B—C14B116.37 (14)H8W1—O8W—H8W2104.4
O6B—C15B—C14B120.28 (14)
C10A—C1A—C2A—C3A61.75 (18)O1C—C3C—C4C—C19C47.42 (16)
C1A—C2A—C3A—O1A176.19 (13)C2C—C3C—C4C—C19C74.85 (16)
C1A—C2A—C3A—C4A59.19 (18)O1C—C3C—C4C—C18C67.01 (15)
O1A—C3A—C4A—C19A45.47 (17)C2C—C3C—C4C—C18C170.72 (12)
C2A—C3A—C4A—C19A76.44 (17)O1C—C3C—C4C—C5C174.23 (11)
O1A—C3A—C4A—C18A70.60 (16)C2C—C3C—C4C—C5C51.96 (16)
C2A—C3A—C4A—C18A167.49 (13)C19C—C4C—C5C—C6C54.66 (17)
O1A—C3A—C4A—C5A171.99 (12)C18C—C4C—C5C—C6C62.75 (16)
C2A—C3A—C4A—C5A50.08 (17)C3C—C4C—C5C—C6C179.70 (12)
C19A—C4A—C5A—C6A51.39 (17)C19C—C4C—C5C—C10C76.02 (17)
C3A—C4A—C5A—C6A176.92 (13)C18C—C4C—C5C—C10C166.58 (13)
C18A—C4A—C5A—C6A66.30 (17)C3C—C4C—C5C—C10C49.62 (16)
C19A—C4A—C5A—C10A80.30 (17)C4C—C5C—C6C—C7C170.38 (13)
C3A—C4A—C5A—C10A45.23 (18)C10C—C5C—C6C—C7C56.78 (17)
C18A—C4A—C5A—C10A162.01 (13)C5C—C6C—C7C—C8C56.37 (18)
C4A—C5A—C6A—C7A166.18 (13)C6C—C7C—C8C—C17C173.98 (14)
C10A—C5A—C6A—C7A59.06 (17)C6C—C7C—C8C—C9C57.90 (18)
C5A—C6A—C7A—C8A54.88 (18)C13C—O3C—C9C—C11C9.88 (15)
C6A—C7A—C8A—C17A175.67 (14)C13C—O3C—C9C—C8C109.87 (13)
C6A—C7A—C8A—C9A55.12 (18)C13C—O3C—C9C—C10C131.01 (12)
C13A—O3A—C9A—C11A9.44 (15)C7C—C8C—C9C—O3C59.32 (16)
C13A—O3A—C9A—C8A109.92 (13)C17C—C8C—C9C—O3C65.97 (17)
C13A—O3A—C9A—C10A131.32 (12)C7C—C8C—C9C—C11C174.30 (13)
C7A—C8A—C9A—O3A58.60 (16)C17C—C8C—C9C—C11C49.02 (18)
C17A—C8A—C9A—O3A66.91 (17)C7C—C8C—C9C—C10C58.87 (16)
C7A—C8A—C9A—C11A173.34 (13)C17C—C8C—C9C—C10C175.84 (13)
C17A—C8A—C9A—C11A47.83 (18)C2C—C1C—C10C—C20C67.96 (16)
C7A—C8A—C9A—C10A58.77 (16)C2C—C1C—C10C—C5C55.96 (16)
C17A—C8A—C9A—C10A175.72 (13)C2C—C1C—C10C—C9C173.97 (12)
C2A—C1A—C10A—C20A71.14 (16)C6C—C5C—C10C—C1C177.10 (12)
C2A—C1A—C10A—C5A53.51 (16)C4C—C5C—C10C—C1C51.33 (16)
C2A—C1A—C10A—C9A169.50 (12)C6C—C5C—C10C—C20C62.02 (16)
C6A—C5A—C10A—C1A179.46 (12)C4C—C5C—C10C—C20C69.55 (17)
C4A—C5A—C10A—C1A46.78 (17)C6C—C5C—C10C—C9C57.55 (15)
C6A—C5A—C10A—C20A58.76 (16)C4C—C5C—C10C—C9C170.88 (12)
C4A—C5A—C10A—C20A73.92 (17)O3C—C9C—C10C—C1C56.95 (15)
C6A—C5A—C10A—C9A61.77 (15)C11C—C9C—C10C—C1C58.35 (16)
C4A—C5A—C10A—C9A165.55 (13)C8C—C9C—C10C—C1C175.72 (12)
O3A—C9A—C10A—C1A59.61 (15)O3C—C9C—C10C—C20C175.85 (12)
C11A—C9A—C10A—C1A55.55 (17)C11C—C9C—C10C—C20C60.55 (17)
C8A—C9A—C10A—C1A178.27 (12)C8C—C9C—C10C—C20C65.38 (15)
O3A—C9A—C10A—C20A178.33 (12)O3C—C9C—C10C—C5C60.70 (15)
C11A—C9A—C10A—C20A63.17 (16)C11C—C9C—C10C—C5C176.00 (13)
C8A—C9A—C10A—C20A63.01 (15)C8C—C9C—C10C—C5C58.07 (15)
O3A—C9A—C10A—C5A57.69 (14)O3C—C9C—C11C—C12C22.14 (15)
C11A—C9A—C10A—C5A172.85 (13)C8C—C9C—C11C—C12C95.67 (15)
C8A—C9A—C10A—C5A60.97 (15)C10C—C9C—C11C—C12C139.63 (13)
O3A—C9A—C11A—C12A23.53 (15)C9C—C11C—C12C—C13C25.90 (16)
C8A—C9A—C11A—C12A94.38 (15)C9C—O3C—C13C—C16C111.85 (13)
C10A—C9A—C11A—C12A140.48 (13)C9C—O3C—C13C—C14C129.77 (12)
C9A—C11A—C12A—C13A28.59 (16)C9C—O3C—C13C—C12C6.43 (15)
C9A—O3A—C13A—C14A132.02 (13)C11C—C12C—C13C—O3C20.03 (15)
C9A—O3A—C13A—C16A108.44 (14)C11C—C12C—C13C—C16C98.12 (15)
C9A—O3A—C13A—C12A8.61 (16)C11C—C12C—C13C—C14C137.29 (14)
C11A—C12A—C13A—O3A22.89 (16)O3C—C13C—C14C—C15C167.55 (12)
C11A—C12A—C13A—C14A137.83 (14)C16C—C13C—C14C—C15C49.32 (17)
C11A—C12A—C13A—C16A94.57 (15)C12C—C13C—C14C—C15C75.26 (18)
O3A—C13A—C14A—C15A175.72 (13)C13C—C14C—C15C—O6C65.40 (19)
C16A—C13A—C14A—C15A66.27 (19)C13C—C14C—C15C—O5C114.79 (16)
C12A—C13A—C14A—C15A59.9 (2)C13C—C14C—C15C—Na432.9 (5)
C13A—C14A—C15A—O5A176.36 (14)O3C—C13C—C16C—O4C62.06 (15)
C13A—C14A—C15A—O6A2.8 (2)C14C—C13C—C16C—O4C54.09 (16)
O3A—C13A—C16A—O4A51.79 (17)C12C—C13C—C16C—O4C178.03 (12)
C14A—C13A—C16A—O4A62.89 (17)C19C—C4C—C18C—O2C174.32 (13)
C12A—C13A—C16A—O4A166.72 (13)C3C—C4C—C18C—O2C55.48 (16)
C19A—C4A—C18A—O2A174.20 (13)C5C—C4C—C18C—O2C62.97 (16)
C3A—C4A—C18A—O2A54.87 (17)C10D—C1D—C2D—C3D59.64 (17)
C5A—C4A—C18A—O2A63.86 (17)C1D—C2D—C3D—O1D176.30 (13)
C10B—C1B—C2B—C3B59.07 (19)C1D—C2D—C3D—C4D59.05 (17)
C1B—C2B—C3B—O1B177.61 (14)O1D—C3D—C4D—C19D50.15 (16)
C1B—C2B—C3B—C4B58.35 (19)C2D—C3D—C4D—C19D72.32 (16)
O1B—C3B—C4B—C18B65.78 (16)O1D—C3D—C4D—C18D63.70 (15)
C2B—C3B—C4B—C18B172.34 (13)C2D—C3D—C4D—C18D173.83 (12)
O1B—C3B—C4B—C19B48.73 (18)O1D—C3D—C4D—C5D176.52 (12)
C2B—C3B—C4B—C19B73.15 (18)C2D—C3D—C4D—C5D54.05 (16)
O1B—C3B—C4B—C5B175.85 (12)C19D—C4D—C5D—C6D56.58 (17)
C2B—C3B—C4B—C5B53.97 (17)C18D—C4D—C5D—C6D60.15 (17)
C3B—C4B—C5B—C6B176.20 (13)C3D—C4D—C5D—C6D178.53 (12)
C18B—C4B—C5B—C6B58.57 (18)C19D—C4D—C5D—C10D73.79 (17)
C19B—C4B—C5B—C6B58.71 (18)C18D—C4D—C5D—C10D169.48 (13)
C3B—C4B—C5B—C10B52.95 (17)C3D—C4D—C5D—C10D51.10 (16)
C18B—C4B—C5B—C10B170.58 (14)C4D—C5D—C6D—C7D171.40 (13)
C19B—C4B—C5B—C10B72.14 (18)C10D—C5D—C6D—C7D56.01 (17)
C10B—C5B—C6B—C7B57.30 (17)C5D—C6D—C7D—C8D55.47 (19)
C4B—C5B—C6B—C7B169.80 (13)C6D—C7D—C8D—C17D174.58 (14)
C5B—C6B—C7B—C8B57.76 (17)C6D—C7D—C8D—C9D57.41 (18)
C6B—C7B—C8B—C17B172.11 (14)C13D—O3D—C9D—C11D8.75 (15)
C6B—C7B—C8B—C9B59.28 (17)C13D—O3D—C9D—C8D110.81 (13)
C13B—O3B—C9B—C11B6.25 (16)C13D—O3D—C9D—C10D130.72 (12)
C13B—O3B—C9B—C8B113.34 (13)C7D—C8D—C9D—O3D58.83 (16)
C13B—O3B—C9B—C10B127.62 (13)C17D—C8D—C9D—O3D66.37 (17)
C7B—C8B—C9B—O3B59.43 (16)C7D—C8D—C9D—C11D173.71 (13)
C17B—C8B—C9B—O3B66.16 (17)C17D—C8D—C9D—C11D48.51 (19)
C7B—C8B—C9B—C11B174.47 (12)C7D—C8D—C9D—C10D59.04 (16)
C17B—C8B—C9B—C11B48.89 (18)C17D—C8D—C9D—C10D175.76 (13)
C7B—C8B—C9B—C10B59.36 (16)C2D—C1D—C10D—C20D69.94 (16)
C17B—C8B—C9B—C10B175.05 (13)C2D—C1D—C10D—C5D53.81 (16)
C2B—C1B—C10B—C20B69.42 (16)C2D—C1D—C10D—C9D172.49 (12)
C2B—C1B—C10B—C5B54.53 (17)C6D—C5D—C10D—C1D177.88 (12)
C2B—C1B—C10B—C9B171.89 (13)C4D—C5D—C10D—C1D50.59 (16)
C6B—C5B—C10B—C1B175.55 (13)C6D—C5D—C10D—C20D62.14 (17)
C4B—C5B—C10B—C1B52.94 (17)C4D—C5D—C10D—C20D69.39 (17)
C6B—C5B—C10B—C20B63.43 (17)C6D—C5D—C10D—C9D57.92 (16)
C4B—C5B—C10B—C20B68.07 (18)C4D—C5D—C10D—C9D170.55 (12)
C6B—C5B—C10B—C9B57.08 (16)O3D—C9D—C10D—C1D59.03 (15)
C4B—C5B—C10B—C9B171.42 (13)C11D—C9D—C10D—C1D56.84 (16)
O3B—C9B—C10B—C1B56.23 (15)C8D—C9D—C10D—C1D177.21 (12)
C11B—C9B—C10B—C1B60.14 (16)O3D—C9D—C10D—C20D176.82 (12)
C8B—C9B—C10B—C1B174.27 (12)C11D—C9D—C10D—C20D60.95 (17)
O3B—C9B—C10B—C20B175.54 (12)C8D—C9D—C10D—C20D65.00 (16)
C11B—C9B—C10B—C20B59.18 (17)O3D—C9D—C10D—C5D59.19 (15)
C8B—C9B—C10B—C20B66.42 (16)C11D—C9D—C10D—C5D175.06 (13)
O3B—C9B—C10B—C5B60.44 (15)C8D—C9D—C10D—C5D58.99 (15)
C11B—C9B—C10B—C5B176.80 (13)O3D—C9D—C11D—C12D21.86 (16)
C8B—C9B—C10B—C5B57.60 (15)C8D—C9D—C11D—C12D95.58 (15)
O3B—C9B—C11B—C12B20.81 (16)C10D—C9D—C11D—C12D139.88 (13)
C8B—C9B—C11B—C12B96.06 (15)C9D—C11D—C12D—C13D26.59 (16)
C10B—C9B—C11B—C12B139.64 (13)C9D—O3D—C13D—C16D109.88 (13)
C9B—C11B—C12B—C13B27.16 (16)C9D—O3D—C13D—C12D8.01 (16)
C9B—O3B—C13B—C16B106.80 (14)C9D—O3D—C13D—C14D131.59 (12)
C9B—O3B—C13B—C14B132.70 (12)C11D—C12D—C13D—O3D21.39 (16)
C9B—O3B—C13B—C12B10.88 (16)C11D—C12D—C13D—C16D95.49 (15)
C11B—C12B—C13B—O3B23.37 (16)C11D—C12D—C13D—C14D138.06 (14)
C11B—C12B—C13B—C16B93.76 (15)O3D—C13D—C14D—C15D165.28 (12)
C11B—C12B—C13B—C14B139.27 (14)C16D—C13D—C14D—C15D48.21 (17)
O3B—C13B—C14B—C15B171.70 (13)C12D—C13D—C14D—C15D77.91 (18)
C16B—C13B—C14B—C15B69.74 (18)C13D—C14D—C15D—O5D101.43 (17)
C12B—C13B—C14B—C15B56.1 (2)C13D—C14D—C15D—O6D79.17 (18)
C13B—C14B—C15B—O5B177.70 (14)O3D—C13D—C16D—O4D54.97 (16)
C13B—C14B—C15B—O6B3.3 (2)C12D—C13D—C16D—O4D170.19 (12)
O3B—C13B—C16B—O4B49.82 (16)C14D—C13D—C16D—O4D60.32 (16)
C14B—C13B—C16B—O4B66.87 (17)C19D—C4D—C18D—O2D172.40 (13)
C12B—C13B—C16B—O4B164.63 (12)C3D—C4D—C18D—O2D53.92 (16)
C3B—C4B—C18B—O2B66.12 (17)C5D—C4D—C18D—O2D65.02 (17)
C19B—C4B—C18B—O2B174.97 (14)C2E—N1E—C1E—O1E2.7 (3)
C5B—C4B—C18B—O2B51.40 (19)C3E—N1E—C1E—O1E179.8 (2)
C10C—C1C—C2C—C3C60.64 (17)C3F—N1F—C1F—O1F2.4 (3)
C1C—C2C—C3C—O1C177.91 (13)C2F—N1F—C1F—O1F180.0 (2)
C1C—C2C—C3C—C4C57.88 (17)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2OA···O2Wii0.822.142.8513 (17)145
O1A—H1A···O6Aii0.821.982.7797 (16)166
O4A—H4A···O6B0.821.892.7066 (17)173
O2B—H2OB···O2Di0.821.992.7717 (17)160
O1B—H1B···O6Bi0.822.022.8395 (18)174
O4B—H4B···O6A0.821.842.6347 (16)164
O4B—H4B···O5A0.822.663.2812 (17)134
O2C—H2OC···O6Ci0.822.032.8200 (17)162
O1C—H1C···O6Ci0.822.022.8198 (17)165
O4C—H4OC···O1E0.821.942.7494 (18)169
O2D—H2OD···O6Dii0.821.902.6949 (17)162
O1D—H1D···O6Dii0.822.062.8563 (17)166
O4D—H4OD···O6W0.822.142.8013 (17)138
O1W—H1W1···O4Ai0.851.972.717 (2)146
O1W—H1W2···O4B0.852.603.173 (2)125
O2W—H2W1···O3Ai0.852.253.0748 (17)163
O2W—H2W1···O4Ai0.852.573.1303 (18)125
O2W—H2W2···O5Ci0.851.942.7856 (17)176
O3W—H3W1···O4B0.851.952.7824 (18)166
O3W—H3W1···O3B0.852.793.3375 (18)124
O4W—H4W1···O6D0.851.962.8022 (18)169
O4W—H4W1···O5D0.852.553.0552 (16)119
O4W—H4W2···O1E0.852.112.9033 (19)156
O5W—H5W1···O4C0.852.222.8571 (19)131
O5W—H5W1···O3C0.852.503.2706 (18)152
O5W—H5W2···O2C0.852.002.8224 (18)163
O6W—H6W2···O2D0.852.132.9575 (17)163
O6W—H6W1···O5B0.852.002.7872 (17)154
O7W—H7W1···O1A0.852.092.9366 (19)175
O7W—H7W2···O1Ciii0.852.112.9577 (19)175
O8W—H8W2···O1B0.852.173.023 (2)176
O8W—H8W1···O1Div0.852.193.027 (2)171
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+1, y, z1; (iv) x2, y, z1.

Experimental details

Crystal data
Chemical formulaNa+·C20H33O6·0.5C3H7NO·2H2O
Mr465.04
Crystal system, space groupMonoclinic, P21
Temperature (K)130
a, b, c (Å)10.7614 (2), 31.0703 (5), 14.7131 (3)
β (°) 110.948 (2)
V3)4594.32 (15)
Z8
Radiation typeCu Kα
µ (mm1)1.01
Crystal size (mm)0.3 × 0.2 × 0.2
Data collection
DiffractometerOxford Diffraction SuperNova
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.655, 0.818
No. of measured, independent and
observed [I > 2σ(I)] reflections
70056, 18050, 17865
Rint0.030
(sin θ/λ)max1)0.631
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.086, 1.03
No. of reflections18050
No. of parameters1143
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.55, 0.29
Absolute structureFlack (1983), with 8192 Friedel pairs
Absolute structure parameter0.03 (3)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR2004 (Burla et al., 2005), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top
Na1—O2B2.3488 (16)Na3—O5D2.3479 (12)
Na1—O1W2.3917 (18)Na3—O5C2.3640 (12)
Na1—O2W2.4151 (16)Na3—O5A2.4036 (13)
Na1—O3W2.5605 (16)Na3—O4C2.5108 (14)
Na1—O5Bi2.6656 (14)Na3—O4D2.5130 (13)
Na1—O6Bi2.9399 (15)Na3—O5B2.5358 (14)
Na2—O5A2.2860 (12)Na4—O1F2.2610 (16)
Na2—O5W2.3124 (16)Na4—O4Wii2.2782 (14)
Na2—O2Ai2.3841 (13)Na4—O6W2.3304 (15)
Na2—O5D2.3928 (13)Na4—O5C2.3856 (13)
Na2—O3W2.4779 (15)Na4—O6C2.4619 (14)
Na2—O4W2.5377 (14)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2OA···O2Wii0.822.142.8513 (17)145
O1A—H1A···O6Aii0.821.982.7797 (16)166
O4A—H4A···O6B0.821.892.7066 (17)173
O2B—H2OB···O2Di0.821.992.7717 (17)160
O1B—H1B···O6Bi0.822.022.8395 (18)174
O4B—H4B···O6A0.821.842.6347 (16)164
O4B—H4B···O5A0.822.663.2812 (17)134
O2C—H2OC···O6Ci0.822.032.8200 (17)162
O1C—H1C···O6Ci0.822.022.8198 (17)165
O4C—H4OC···O1E0.821.942.7494 (18)169
O2D—H2OD···O6Dii0.821.902.6949 (17)162
O1D—H1D···O6Dii0.822.062.8563 (17)166
O4D—H4OD···O6W0.822.142.8013 (17)138
O1W—H1W1···O4Ai0.851.972.717 (2)146
O1W—H1W2···O4B0.852.603.173 (2)125
O2W—H2W1···O3Ai0.852.253.0748 (17)163
O2W—H2W1···O4Ai0.852.573.1303 (18)125
O2W—H2W2···O5Ci0.851.942.7856 (17)176
O3W—H3W1···O4B0.851.952.7824 (18)166
O3W—H3W1···O3B0.852.793.3375 (18)124
O4W—H4W1···O6D0.851.962.8022 (18)169
O4W—H4W1···O5D0.852.553.0552 (16)119
O4W—H4W2···O1E0.852.112.9033 (19)156
O5W—H5W1···O4C0.852.222.8571 (19)131
O5W—H5W1···O3C0.852.503.2706 (18)152
O5W—H5W2···O2C0.852.002.8224 (18)163
O6W—H6W2···O2D0.852.132.9575 (17)163
O6W—H6W1···O5B0.852.002.7872 (17)154
O7W—H7W1···O1A0.852.092.9366 (19)175
O7W—H7W2···O1Ciii0.852.112.9577 (19)175
O8W—H8W2···O1B0.852.173.023 (2)176
O8W—H8W1···O1Div0.852.193.027 (2)171
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+1, y, z1; (iv) x2, y, z1.
 

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