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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1308–m1309.
Published online 2009 October 7. doi:  10.1107/S1600536809039993
PMCID: PMC2971272

catena-Poly[[sodium-di-μ-β-d-glucose] chloride]

Abstract

The asymmetric unit of the title compound, {[Na(C6H12O6)2]Cl}n, contains six glucose mol­ecules, three Na+ ions and three Cl ions, i.e. three independent {[Na(C6H12O6)2]Cl} units. Each of these units forms polymeric chains along the c axis. Each Na+ ion is surrounded by six O atoms from four glucose mol­ecules, forming a distorted octa­hedral geometry. All glucose mol­ecules adopt chair conformations. The constituent units are linked into a three-dimensional framework by O—H(...)Cl and O—H(...)O hydrogen bonds, utilizing all the O—H groups.

Related literature

For general background to H. sagittifolia and its use in folk medicine, see: Duke (1985 [triangle]); Burkill (1966 [triangle]); Sulaiman & Boyce (2005 [triangle]). For the crystal structure of the monohydrated analogue, see: Ferguson et al. (1991 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1308-scheme1.jpg

Experimental

Crystal data

  • [Na(C6H12O6)2]Cl
  • M r = 418.75
  • Trigonal, An external file that holds a picture, illustration, etc.
Object name is e-65-m1308-efi3.jpg
  • a = 16.3795 (4) Å
  • c = 17.4232 (6) Å
  • V = 4048.2 (2) Å3
  • Z = 9
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 100 K
  • 0.50 × 0.38 × 0.26 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.815, T max = 0.928
  • 211137 measured reflections
  • 27007 independent reflections
  • 25094 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.111
  • S = 1.06
  • 27007 reflections
  • 715 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.80 e Å−3
  • Δρmin = −0.40 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 13472 Friedel pairs
  • Flack parameter: 0.02 (3)

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039993/ci2906sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039993/ci2906Isup2.hkl

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

Acknowledgments

KCW and AH are grateful for financial support from Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/pkimia/811050). AH and CKQ thank the Institute of Postgraduate Studies (IPS) for USM fellowships. HKF and CKQ thank USM for the Research University Golden Goose Grant (No. 1001/PFIZIK/811012).

supplementary crystallographic information

Comment

Research in phytochemical study often results in discovery of novel and interesting secondary metabolites from medical plants. Homalomena sagittifolia Jungh, which belongs to Araceae family, is a small herb found growing in damp, wet and low open spaces in the forest of Malaysia. The genus Homalomena has an overwhelmingly Asian distribution with greatest number of species occurring in archipelagic Malaysia as reported by Sulaiman & Boyce (2005). The folklores regarding the species are rich enough to be mentioned in CRC hand book of medicinal plants (Duke, 1985). In Malaysia, leaves of H. sagittifolia are used as a poultice to cure leg sores. A decoction of the rhizomes and leaves is given to drink for fever (Burkill, 1966). So far, no extensive phytochemical study of H. sagittifolia has been performed. As part of our on-going search for chemical constituents, we investigated the leaves of H. sagittifolia, which lead to isolation of the title compound. Herein, we report the crystal structure of the title compound.

The asymmetric unit contains three independent [Na(C6H12O6)2]+ units [say A, B and C] and three Cl- ions (Fig. 1). Each of these independent units form polymeric chains along the c-axis. Each Na+ ion is surrounded by six O atoms from two independent and two symmetry related glucose molecules to form a distorted octahedral geometry, with Na—O distances ranging from 2.3433 (16) to 2.3966 (15) Å, 2.3455 (15) to 2.3957 (16) Å and 2.3040 (16) to 2.4372 (16) Å, for units A, B and C, respectively, whereas, the angles around the Na+ ion range from 68.64 (5) to 138.92 (6)°, 68.99 (5) to 138.99 (6)° and 69.07 (5) to 137.05 (6)° for units A, B and C, respectively. Bond lengths and angles are within normal ranges, and comparable to a closely related structure (Ferguson et al., 1991). All the six independent glucose units in the asymmetric unit adopt chair conformations. The puckering parameters (Cremer & Pople, 1975) are Q = 0.580 (2) Å, Θ = 2.1 (2)° and [var phi] = 333 (6)° for O1A/C1A–C5A ring, Q = 0.570 (2) Å, Θ = 1.3 (2)° and [var phi] = 83 (12)° for O7A/C7A–C11A ring, Q = 0.573 (2) Å, Θ = 0.0 (2)° and [var phi] = 31 (8)° for O1B/C1B–C5B) ring, Q = 0.577 (2) Å, Θ = 0.0 (2)° and [var phi] = 9 (11)° for O7B/C7B–C11B ring, Q = 0.570 (2) Å, Θ = 0.0 (2)° and [var phi] = 66 (6)° for O1C/C1C–C5C ring, and Q = 0.580 (2) Å; Θ = 0.4 (2)° and [var phi] = 3 (10)° for O7C/C7C–C11C ring.

In the crystal, the constituent units are linked into a three-dimensional framework (Fig. 3) by O—H···Cl and O—H···O hydrogen bonds (Table 1), utilizing all the O-H groups.

Experimental

The title compound was isolated from the methanolic extract of the leaves of H. sagittifolia. The crude extract was fractionated by using Sephadex LH-20 CC eluting with methanol-water (1:1). Fraction-9 was subjected to silica-gel column chromatography, repeatedly eluting with chloroform-methanol solvent mixture with their ratio ranging from 90:10–70:30. Finally, colourless single crystals were grown from a methanol-acetone solution.

Refinement

O-bound H atoms were initially located in difference maps and later their positions were fixed, with O-H = 0.81–0.93 Å, and refined as riding with the parent atom with Uiso(H) = 1.5Ueq(O). C-bound H atoms were placed in calculated positions, with C–H = 0.97 and 0.98 Å, and refined using a riding model, with Uiso(H) = 1.2 Ueq(C). The crystal under investigation was twinned and the use of the twin law (1 1 0/0 -1 0/ 0 0 -1) resulted in a BASF parameter (SHELXTL; Sheldrick, 2008) of 0.3315 (8).

Figures

Fig. 1.
The asymmetric unit of the title compound, showing the atom-numbering scheme. H atoms have been omitted for clarity.
Fig. 2.
Part of a polymeric chain formed by Na1A ions, showing the coordination environment. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity. Symmetry codes: (#) -x+y, 1-x, -1/3+z; ($) 1-y, 1+x-y, 1/3+z.
Fig. 3.
The crystal packing of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines. C-bound H atoms have been omitted for clarity.

Crystal data

[Na(C6H12O6)2]ClDx = 1.546 Mg m3
Mr = 418.75Mo Kα radiation, λ = 0.71073 Å
Trigonal, P31Cell parameters from 9874 reflections
Hall symbol: P 31θ = 2.5–34.9°
a = 16.3795 (4) ŵ = 0.30 mm1
c = 17.4232 (6) ÅT = 100 K
V = 4048.2 (2) Å3Block, colourless
Z = 90.50 × 0.38 × 0.26 mm
F(000) = 1980

Data collection

Bruker SMART APEXII CCD area-detector diffractometer27007 independent reflections
Radiation source: fine-focus sealed tube25094 reflections with I > 2σ(I)
graphiteRint = 0.050
[var phi] and ω scansθmax = 36.8°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −27→27
Tmin = 0.815, Tmax = 0.928k = −27→27
211137 measured reflectionsl = −29→29

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.111w = 1/[σ2(Fo2) + (0.0718P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
27007 reflectionsΔρmax = 0.80 e Å3
715 parametersΔρmin = −0.40 e Å3
1 restraintAbsolute structure: Flack (1983), 13472 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (3)

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Na1A0.40243 (6)0.79506 (6)0.70138 (4)0.01379 (13)
O1A0.42335 (10)0.97603 (9)0.90774 (7)0.0147 (2)
O2A0.37480 (10)0.88583 (10)0.79491 (8)0.0161 (2)
H2A0.34870.91640.77920.024*
O3A0.51727 (9)0.84858 (10)0.80086 (8)0.0155 (2)
H3A0.57530.86450.80130.023*
O4A0.47353 (11)0.75675 (11)0.95023 (8)0.0184 (2)
H4A0.46280.71170.92290.028*
O5A0.32729 (10)0.76721 (9)1.03053 (7)0.0155 (2)
H5A0.33950.78961.07450.023*
O6A0.39899 (12)0.99572 (10)1.07224 (8)0.0208 (3)
H6A0.40100.95951.10370.031*
O7A0.56259 (10)0.94644 (9)0.48723 (8)0.0152 (2)
O8A0.51828 (9)0.86139 (10)0.60264 (8)0.0154 (2)
H8A0.57470.88290.61780.023*
O9A0.36105 (10)0.87692 (11)0.61387 (8)0.0180 (2)
H9A0.32060.89490.61180.027*
O10A0.27167 (10)0.77955 (11)0.47331 (9)0.0213 (3)
H10A0.23510.73500.50010.032*
O11A0.39410 (10)0.74111 (10)0.37729 (8)0.0180 (2)
H11A0.36260.74340.33950.027*
O12A0.58050 (12)0.95678 (11)0.32001 (9)0.0255 (3)
H12A0.53050.92820.29670.038*
C1A0.45104 (12)0.94345 (12)0.84180 (10)0.0139 (3)
H1D0.49710.99790.81210.017*
C2A0.49595 (12)0.88519 (12)0.86730 (10)0.0125 (3)
H2D0.55420.92570.89560.015*
C3A0.42781 (12)0.80420 (12)0.91894 (9)0.0125 (2)
H3D0.37280.75960.88890.015*
C4A0.39598 (12)0.84212 (12)0.98499 (10)0.0129 (3)
H4D0.45060.88231.01720.015*
C5A0.35402 (12)0.90065 (12)0.95469 (10)0.0131 (3)
H5D0.29860.86040.92320.016*
C6A0.32521 (13)0.94381 (13)1.01897 (11)0.0180 (3)
H6D0.30520.98530.99680.022*
H6E0.27180.89391.04610.022*
C7A0.51247 (12)0.92956 (12)0.55789 (10)0.0138 (3)
H7D0.53900.98860.58690.017*
C8A0.40834 (12)0.89450 (12)0.54197 (10)0.0137 (3)
H8D0.40260.94370.51470.016*
C9A0.36633 (12)0.80596 (12)0.49278 (10)0.0143 (3)
H9D0.36670.75480.52170.017*
C10A0.42518 (12)0.82541 (12)0.41974 (10)0.0139 (3)
H10D0.41880.87140.38810.017*
C11A0.52941 (12)0.86400 (11)0.43898 (10)0.0139 (3)
H11D0.53570.81560.46710.017*
C12A0.59197 (14)0.89208 (14)0.36868 (11)0.0199 (3)
H12D0.65730.92110.38480.024*
H12E0.57730.83590.33950.024*
Na1B0.87325 (6)0.92592 (5)1.03422 (4)0.01344 (13)
O1B0.70647 (9)0.91250 (10)0.82118 (8)0.0149 (2)
O2B0.79165 (10)0.95978 (10)0.93703 (8)0.0159 (2)
H2B0.76400.98810.95440.024*
O3B0.79791 (11)0.79928 (10)0.94733 (8)0.0183 (2)
H3B0.78380.74180.94620.028*
O4B0.89994 (11)0.82099 (11)0.80581 (9)0.0207 (3)
H4B0.95440.84460.82130.031*
O5B0.91942 (9)0.97609 (10)0.71147 (8)0.0171 (2)
H5B0.93210.94000.68540.026*
O6B0.69713 (11)0.92403 (12)0.65406 (9)0.0221 (3)
H6B0.73080.91500.62450.033*
O7B0.70408 (9)0.75684 (9)1.24067 (7)0.0139 (2)
O8B0.79839 (10)0.80594 (9)1.12998 (8)0.0151 (2)
H8B0.81140.75731.13690.023*
O9B0.81132 (10)0.97772 (10)1.13269 (8)0.0155 (2)
H9B0.79261.01761.13430.023*
O10B0.90017 (11)1.03683 (10)1.28298 (8)0.0186 (2)
H10B0.94721.07351.25860.028*
O11B0.90851 (9)0.89131 (10)1.36548 (7)0.0157 (2)
H11B0.89110.87451.40920.024*
O12B0.68312 (10)0.71785 (11)1.40569 (8)0.0206 (3)
H12B0.71320.74551.44410.031*
C1B0.72851 (12)0.88272 (13)0.89236 (10)0.0134 (3)
H1E0.67030.84460.92140.016*
C2B0.77495 (12)0.82421 (12)0.87540 (10)0.0134 (3)
H2E0.73020.76680.84800.016*
C3B0.86262 (12)0.88006 (12)0.82614 (10)0.0141 (3)
H3E0.90990.93410.85560.017*
C4B0.83738 (12)0.91541 (12)0.75406 (10)0.0135 (3)
H4E0.79540.86130.72200.016*
C5B0.78801 (12)0.97057 (12)0.77426 (10)0.0137 (3)
H5E0.83161.02680.80350.016*
C6B0.75485 (14)1.00088 (14)0.70404 (11)0.0199 (3)
H6F0.71941.03060.72060.024*
H6G0.80941.04730.67580.024*
C7B0.73296 (12)0.81654 (12)1.17456 (9)0.0125 (3)
H7E0.67750.80131.14320.015*
C8B0.77960 (12)0.91972 (12)1.19957 (9)0.0124 (2)
H8E0.73330.93041.22670.015*
C9B0.86271 (12)0.94398 (11)1.25254 (9)0.0127 (3)
H9E0.91200.93971.22400.015*
C10B0.82991 (11)0.87510 (12)1.31930 (9)0.0118 (2)
H10E0.78540.88421.35070.014*
C11B0.78116 (12)0.77340 (12)1.29000 (9)0.0126 (2)
H11E0.82670.76371.26070.015*
C12B0.74206 (13)0.70209 (12)1.35467 (10)0.0167 (3)
H12F0.70600.63931.33300.020*
H12G0.79410.70491.38350.020*
Na1C0.72272 (5)0.26194 (6)0.36712 (4)0.01372 (13)
O1C0.87438 (9)0.25866 (10)0.58123 (8)0.0150 (2)
O2C0.83296 (9)0.30390 (10)0.46694 (8)0.0158 (2)
H2C0.88820.33400.44830.024*
O3C0.67052 (10)0.13599 (10)0.45499 (8)0.0180 (2)
H3C0.63250.07690.45480.027*
O4C0.58660 (10)0.15191 (10)0.59700 (9)0.0205 (3)
H4C0.55680.17990.59590.031*
O5C0.71738 (10)0.31138 (10)0.68982 (9)0.0183 (2)
H5C0.67980.27790.72520.027*
O6C0.89548 (12)0.26778 (14)0.74742 (9)0.0251 (3)
H6C0.90690.23170.72310.038*
O7C0.73582 (10)0.09477 (9)0.16154 (7)0.0149 (2)
O8C0.68727 (10)0.13749 (9)0.27402 (8)0.0166 (2)
H8C0.65680.07960.28650.025*
O9C0.83698 (9)0.31498 (10)0.27036 (8)0.0156 (2)
H9C0.89410.35900.26760.023*
O10C0.79948 (11)0.36892 (9)0.12121 (8)0.0177 (2)
H10C0.81870.40690.15670.027*
O11C0.64855 (10)0.21736 (10)0.03950 (7)0.0150 (2)
H11C0.66740.2224−0.00560.022*
O12C0.71783 (12)0.05674 (11)−0.00376 (8)0.0207 (3)
H12C0.72640.1011−0.03110.031*
C1C0.82406 (12)0.22769 (13)0.51041 (10)0.0143 (3)
H1F0.84790.19310.48080.017*
C2C0.71885 (12)0.16317 (12)0.52677 (10)0.0135 (3)
H2F0.70960.10690.55410.016*
C3C0.68206 (12)0.21485 (12)0.57588 (10)0.0138 (3)
H3F0.68550.26750.54650.017*
C4C0.74205 (12)0.25268 (12)0.64813 (10)0.0140 (3)
H4F0.73220.19960.68060.017*
C5C0.84708 (12)0.31259 (13)0.62873 (10)0.0143 (3)
H5F0.85730.36850.60020.017*
C6C0.91000 (14)0.34435 (15)0.69944 (11)0.0193 (3)
H6H0.97540.37830.68330.023*
H6I0.89780.38740.72880.023*
C7C0.76415 (12)0.15386 (12)0.22817 (9)0.0131 (3)
H7F0.80800.14270.25850.016*
C8C0.81344 (12)0.25722 (12)0.20314 (10)0.0123 (3)
H8F0.87130.27250.17520.015*
C9C0.74880 (12)0.27549 (12)0.15133 (10)0.0128 (3)
H9F0.69420.26740.18070.015*
C10C0.71611 (12)0.20734 (12)0.08441 (10)0.0125 (3)
H10F0.77050.22070.05220.015*
C11C0.67005 (12)0.10534 (12)0.11347 (9)0.0127 (3)
H11F0.61400.09120.14370.015*
C12C0.64163 (14)0.03467 (13)0.04824 (11)0.0172 (3)
H12H0.6195−0.02770.06950.021*
H12I0.58990.03330.02010.021*
Cl10.47325 (3)0.25978 (4)0.54724 (3)0.02033 (8)
Cl20.42150 (4)0.86126 (3)0.18827 (3)0.02115 (8)
Cl30.12199 (4)0.92863 (4)0.85610 (3)0.02089 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Na1A0.0151 (3)0.0151 (3)0.0119 (3)0.0081 (3)0.0010 (2)0.0004 (2)
O1A0.0206 (6)0.0113 (5)0.0130 (5)0.0085 (4)0.0028 (4)0.0017 (4)
O2A0.0204 (6)0.0188 (6)0.0139 (5)0.0135 (5)−0.0035 (4)−0.0023 (4)
O3A0.0134 (5)0.0211 (6)0.0139 (5)0.0100 (5)0.0004 (4)−0.0030 (4)
O4A0.0273 (7)0.0211 (6)0.0149 (5)0.0183 (6)0.0009 (5)0.0035 (4)
O5A0.0191 (6)0.0119 (5)0.0123 (5)0.0052 (4)0.0033 (4)0.0014 (4)
O6A0.0338 (7)0.0143 (6)0.0149 (6)0.0124 (5)−0.0020 (5)−0.0033 (4)
O7A0.0170 (5)0.0110 (5)0.0124 (5)0.0030 (4)0.0012 (4)−0.0010 (4)
O8A0.0135 (5)0.0186 (6)0.0138 (5)0.0078 (4)−0.0006 (4)0.0032 (4)
O9A0.0206 (6)0.0238 (6)0.0154 (5)0.0154 (5)0.0042 (4)0.0044 (5)
O10A0.0147 (6)0.0213 (6)0.0286 (7)0.0094 (5)−0.0051 (5)−0.0033 (5)
O11A0.0192 (6)0.0147 (5)0.0202 (6)0.0087 (5)−0.0071 (5)−0.0067 (4)
O12A0.0297 (8)0.0183 (6)0.0161 (6)0.0027 (5)−0.0004 (5)0.0035 (5)
C1A0.0169 (7)0.0124 (6)0.0126 (7)0.0074 (5)0.0012 (5)0.0007 (5)
C2A0.0132 (6)0.0134 (6)0.0109 (6)0.0066 (5)0.0000 (5)−0.0005 (5)
C3A0.0154 (6)0.0131 (6)0.0107 (6)0.0083 (5)0.0003 (5)−0.0003 (5)
C4A0.0149 (6)0.0114 (6)0.0112 (6)0.0057 (5)0.0006 (5)0.0002 (5)
C5A0.0126 (6)0.0125 (6)0.0135 (6)0.0058 (5)0.0009 (5)−0.0006 (5)
C6A0.0225 (8)0.0175 (7)0.0168 (7)0.0121 (6)0.0047 (6)−0.0011 (5)
C7A0.0159 (6)0.0129 (6)0.0107 (6)0.0058 (5)0.0005 (5)0.0006 (5)
C8A0.0172 (7)0.0137 (6)0.0125 (6)0.0093 (5)−0.0003 (5)0.0013 (5)
C9A0.0131 (6)0.0129 (6)0.0162 (7)0.0060 (5)−0.0019 (5)−0.0001 (5)
C10A0.0167 (7)0.0120 (6)0.0133 (6)0.0074 (5)−0.0032 (5)−0.0019 (5)
C11A0.0159 (7)0.0111 (6)0.0128 (6)0.0054 (5)0.0009 (5)0.0009 (5)
C12A0.0196 (7)0.0190 (7)0.0176 (7)0.0072 (6)0.0037 (6)0.0005 (6)
Na1B0.0138 (3)0.0139 (3)0.0123 (3)0.0067 (3)−0.0006 (2)0.0000 (2)
O1B0.0129 (5)0.0209 (6)0.0122 (5)0.0094 (5)−0.0001 (4)0.0019 (4)
O2B0.0205 (6)0.0171 (5)0.0142 (5)0.0123 (5)−0.0038 (4)−0.0047 (4)
O3B0.0268 (7)0.0152 (5)0.0152 (6)0.0121 (5)−0.0044 (5)−0.0018 (4)
O4B0.0203 (6)0.0194 (6)0.0280 (7)0.0141 (5)0.0026 (5)−0.0006 (5)
O5B0.0142 (5)0.0147 (5)0.0200 (6)0.0055 (4)0.0061 (4)0.0002 (4)
O6B0.0169 (6)0.0339 (8)0.0159 (6)0.0130 (6)−0.0028 (5)−0.0031 (5)
O7B0.0103 (5)0.0142 (5)0.0135 (5)0.0033 (4)0.0000 (4)0.0023 (4)
O8B0.0181 (6)0.0128 (5)0.0140 (5)0.0074 (4)0.0028 (4)0.0002 (4)
O9B0.0217 (6)0.0154 (5)0.0137 (5)0.0126 (5)0.0031 (4)0.0032 (4)
O10B0.0225 (6)0.0130 (5)0.0157 (6)0.0054 (5)−0.0025 (5)−0.0013 (4)
O11B0.0122 (5)0.0195 (6)0.0126 (5)0.0058 (4)−0.0017 (4)0.0020 (4)
O12B0.0152 (6)0.0228 (6)0.0156 (5)0.0033 (5)0.0037 (4)0.0013 (5)
C1B0.0145 (6)0.0165 (7)0.0106 (6)0.0088 (5)−0.0007 (5)−0.0007 (5)
C2B0.0154 (6)0.0127 (6)0.0124 (6)0.0073 (5)−0.0010 (5)−0.0016 (5)
C3B0.0131 (6)0.0130 (6)0.0170 (7)0.0071 (5)0.0005 (5)−0.0018 (5)
C4B0.0119 (6)0.0123 (6)0.0140 (7)0.0045 (5)0.0017 (5)−0.0009 (5)
C5B0.0128 (6)0.0160 (6)0.0123 (6)0.0072 (5)−0.0005 (5)0.0000 (5)
C6B0.0185 (7)0.0232 (8)0.0190 (8)0.0112 (7)−0.0003 (6)0.0035 (6)
C7B0.0117 (6)0.0129 (6)0.0097 (6)0.0036 (5)−0.0001 (4)0.0005 (5)
C8B0.0145 (6)0.0134 (6)0.0104 (6)0.0078 (5)0.0001 (5)0.0005 (5)
C9B0.0131 (6)0.0113 (6)0.0117 (6)0.0047 (5)−0.0010 (5)−0.0002 (5)
C10B0.0110 (6)0.0135 (6)0.0100 (6)0.0054 (5)−0.0005 (4)0.0013 (5)
C11B0.0123 (6)0.0138 (6)0.0108 (6)0.0058 (5)0.0005 (5)0.0011 (5)
C12B0.0177 (7)0.0146 (7)0.0150 (6)0.0059 (6)0.0014 (5)0.0037 (5)
Na1C0.0135 (3)0.0153 (3)0.0120 (3)0.0070 (3)−0.0002 (2)0.0004 (2)
O1C0.0147 (5)0.0220 (6)0.0134 (5)0.0130 (5)−0.0006 (4)−0.0016 (4)
O2C0.0138 (5)0.0167 (5)0.0142 (5)0.0055 (5)0.0017 (4)0.0049 (4)
O3C0.0207 (6)0.0137 (5)0.0143 (5)0.0046 (5)−0.0028 (4)0.0005 (4)
O4C0.0137 (5)0.0163 (6)0.0288 (7)0.0055 (5)0.0053 (5)0.0029 (5)
O5C0.0190 (6)0.0164 (6)0.0213 (6)0.0102 (5)0.0057 (5)−0.0022 (5)
O6C0.0292 (7)0.0432 (9)0.0155 (6)0.0274 (7)0.0010 (5)0.0039 (6)
O7C0.0215 (6)0.0151 (5)0.0123 (5)0.0122 (5)−0.0030 (4)−0.0031 (4)
O8C0.0203 (6)0.0143 (5)0.0131 (5)0.0070 (5)0.0042 (4)0.0020 (4)
O9C0.0138 (5)0.0160 (5)0.0110 (5)0.0029 (4)−0.0009 (4)−0.0031 (4)
O10C0.0250 (6)0.0110 (5)0.0148 (6)0.0071 (5)−0.0006 (5)0.0007 (4)
O11C0.0181 (5)0.0197 (5)0.0126 (5)0.0136 (5)−0.0020 (4)−0.0004 (4)
O12C0.0317 (7)0.0207 (6)0.0163 (6)0.0181 (6)0.0026 (5)−0.0015 (5)
C1C0.0144 (6)0.0176 (7)0.0129 (6)0.0094 (6)−0.0002 (5)0.0000 (5)
C2C0.0139 (6)0.0128 (6)0.0132 (7)0.0061 (5)0.0008 (5)0.0010 (5)
C3C0.0113 (6)0.0129 (6)0.0175 (7)0.0062 (5)0.0027 (5)0.0025 (5)
C4C0.0155 (7)0.0139 (6)0.0149 (7)0.0092 (6)0.0024 (5)0.0010 (5)
C5C0.0153 (7)0.0163 (7)0.0138 (6)0.0097 (6)−0.0009 (5)−0.0011 (5)
C6C0.0187 (8)0.0254 (8)0.0164 (7)0.0129 (7)−0.0050 (6)−0.0050 (6)
C7C0.0168 (7)0.0150 (6)0.0100 (6)0.0098 (6)−0.0013 (5)−0.0015 (5)
C8C0.0129 (6)0.0132 (6)0.0108 (6)0.0065 (5)−0.0005 (5)−0.0007 (5)
C9C0.0148 (6)0.0123 (6)0.0125 (6)0.0078 (5)−0.0003 (5)0.0001 (5)
C10C0.0127 (6)0.0145 (6)0.0126 (6)0.0085 (5)−0.0009 (5)−0.0003 (5)
C11C0.0140 (6)0.0128 (6)0.0113 (6)0.0066 (5)−0.0011 (5)−0.0010 (5)
C12C0.0206 (7)0.0157 (7)0.0156 (7)0.0093 (6)−0.0016 (6)−0.0029 (5)
Cl10.01720 (18)0.0248 (2)0.01575 (17)0.00802 (16)0.00034 (14)−0.00187 (15)
Cl20.0249 (2)0.01823 (18)0.01642 (18)0.00789 (16)−0.00165 (15)0.00035 (14)
Cl30.0260 (2)0.0250 (2)0.01662 (19)0.01643 (18)0.00284 (15)0.00257 (15)

Geometric parameters (Å, °)

Na1A—O9A2.3433 (16)O11B—Na1Biii2.3895 (15)
Na1A—O11Ai2.3447 (16)O11B—H11B0.81
Na1A—O5Aii2.3726 (15)O12B—C12B1.428 (2)
Na1A—O3A2.3795 (15)O12B—H12B0.82
Na1A—O8A2.3831 (15)C1B—C2B1.521 (2)
Na1A—O2A2.3966 (15)C1B—H1E0.98
O1A—C1A1.432 (2)C2B—C3B1.524 (2)
O1A—C5A1.443 (2)C2B—H2E0.98
O2A—C1A1.392 (2)C3B—C4B1.524 (3)
O2A—H2A0.85C3B—H3E0.98
O3A—C2A1.425 (2)C4B—C5B1.525 (2)
O3A—H3A0.85C4B—H4E0.98
O4A—C3A1.430 (2)C5B—C6B1.519 (3)
O4A—H4A0.82C5B—H5E0.98
O5A—C4A1.421 (2)C6B—H6F0.97
O5A—Na1Ai2.3726 (15)C6B—H6G0.97
O5A—H5A0.83C7B—C8B1.529 (2)
O6A—C6A1.420 (2)C7B—H7E0.98
O6A—H6A0.82C8B—C9B1.524 (2)
O7A—C7A1.428 (2)C8B—H8E0.98
O7A—C11A1.446 (2)C9B—C10B1.519 (2)
O8A—C7A1.404 (2)C9B—H9E0.98
O8A—H8A0.85C10B—C11B1.531 (2)
O9A—C8A1.424 (2)C10B—H10E0.98
O9A—H9A0.85C11B—C12B1.515 (2)
O10A—C9A1.427 (2)C11B—H11E0.98
O10A—H10A0.82C12B—H12F0.97
O11A—C10A1.418 (2)C12B—H12G0.97
O11A—Na1Aii2.3447 (15)Na1C—O5Cv2.3040 (16)
O11A—H11A0.85Na1C—O9C2.3397 (15)
O12A—C12A1.441 (3)Na1C—O2C2.3488 (15)
O12A—H12A0.82Na1C—O3C2.3594 (16)
C1A—C2A1.533 (2)Na1C—O11Cvi2.4367 (15)
C1A—H1D0.98Na1C—O8C2.4372 (16)
C2A—C3A1.528 (2)O1C—C1C1.429 (2)
C2A—H2D0.98O1C—C5C1.435 (2)
C3A—C4A1.519 (2)O2C—C1C1.404 (2)
C3A—H3D0.98O2C—H2C0.85
C4A—C5A1.526 (2)O3C—C2C1.427 (2)
C4A—H4D0.98O3C—H3C0.85
C5A—C6A1.520 (2)O4C—C3C1.425 (2)
C5A—H5D0.98O4C—H4C0.82
C6A—H6D0.97O5C—C4C1.416 (2)
C6A—H6E0.97O5C—Na1Cvi2.3040 (16)
C7A—C8A1.529 (2)O5C—H5C0.85
C7A—H7D0.98O6C—C6C1.425 (3)
C8A—C9A1.521 (2)O6C—H6C0.82
C8A—H8D0.98O7C—C7C1.432 (2)
C9A—C10A1.531 (3)O7C—C11C1.442 (2)
C9A—H9D0.98O8C—C7C1.399 (2)
C10A—C11A1.532 (2)O8C—H8C0.85
C10A—H10D0.98O9C—C8C1.432 (2)
C11A—C12A1.513 (2)O9C—H9C0.85
C11A—H11D0.98O10C—C9C1.427 (2)
C12A—H12D0.97O10C—H10C0.82
C12A—H12E0.97O11C—C10C1.430 (2)
Na1B—O5Biii2.3455 (15)O11C—Na1Cv2.4367 (15)
Na1B—O9B2.3565 (16)O11C—H11C0.8325
Na1B—O3B2.3576 (16)O12C—C12C1.435 (2)
Na1B—O2B2.3881 (16)O12C—H12C0.82
Na1B—O11Biv2.3895 (15)C1C—C2C1.532 (2)
Na1B—O8B2.3957 (16)C1C—H1F0.98
O1B—C1B1.443 (2)C2C—C3C1.524 (2)
O1B—C5B1.444 (2)C2C—H2F0.98
O2B—C1B1.401 (2)C3C—C4C1.525 (3)
O2B—H2B0.85C3C—H3F0.98
O3B—C2B1.426 (2)C4C—C5C1.533 (3)
O3B—H3B0.85C4C—H4F0.98
O4B—C3B1.424 (2)C5C—C6C1.521 (2)
O4B—H4B0.82C5C—H5F0.98
O5B—C4B1.417 (2)C6C—H6H0.97
O5B—Na1Biv2.3455 (15)C6C—H6I0.97
O5B—H5B0.85C7C—C8C1.530 (2)
O6B—C6B1.430 (3)C7C—H7F0.98
O6B—H6B0.82C8C—C9C1.530 (2)
O7B—C7B1.430 (2)C8C—H8F0.98
O7B—C11B1.437 (2)C9C—C10C1.515 (2)
O8B—C7B1.403 (2)C9C—H9F0.98
O8B—H8B0.93C10C—C11C1.535 (2)
O9B—C8B1.427 (2)C10C—H10F0.98
O9B—H9B0.85C11C—C12C1.520 (2)
O10B—C9B1.427 (2)C11C—H11F0.98
O10B—H10B0.82C12C—H12H0.97
O11B—C10B1.426 (2)C12C—H12I0.97
O9A—Na1A—O11Ai100.32 (6)C4B—C3B—H3E109.3
O9A—Na1A—O5Aii137.26 (6)O5B—C4B—C3B110.84 (14)
O11Ai—Na1A—O5Aii73.65 (5)O5B—C4B—C5B107.65 (14)
O9A—Na1A—O3A131.66 (6)C3B—C4B—C5B111.08 (14)
O11Ai—Na1A—O3A122.09 (6)O5B—C4B—H4E109.1
O5Aii—Na1A—O3A80.95 (5)C3B—C4B—H4E109.1
O9A—Na1A—O8A70.22 (5)C5B—C4B—H4E109.1
O11Ai—Na1A—O8A132.59 (6)O1B—C5B—C6B107.88 (14)
O5Aii—Na1A—O8A83.08 (5)O1B—C5B—C4B109.28 (14)
O3A—Na1A—O8A93.17 (5)C6B—C5B—C4B112.94 (15)
O9A—Na1A—O2A83.63 (5)O1B—C5B—H5E108.9
O11Ai—Na1A—O2A99.34 (6)C6B—C5B—H5E108.9
O5Aii—Na1A—O2A138.92 (6)C4B—C5B—H5E108.9
O3A—Na1A—O2A68.64 (5)O6B—C6B—C5B112.93 (16)
O8A—Na1A—O2A124.22 (6)O6B—C6B—H6F109.0
C1A—O1A—C5A113.35 (13)C5B—C6B—H6F109.0
C1A—O2A—Na1A115.85 (11)O6B—C6B—H6G109.0
C1A—O2A—H2A109.6C5B—C6B—H6G109.0
Na1A—O2A—H2A116.9H6F—C6B—H6G107.8
C2A—O3A—Na1A115.58 (10)O8B—C7B—O7B111.93 (14)
C2A—O3A—H3A109.5O8B—C7B—C8B107.71 (13)
Na1A—O3A—H3A132.6O7B—C7B—C8B109.74 (13)
C3A—O4A—H4A109.5O8B—C7B—H7E109.1
C4A—O5A—Na1Ai146.82 (11)O7B—C7B—H7E109.1
C4A—O5A—H5A102.8C8B—C7B—H7E109.1
Na1Ai—O5A—H5A110.1O9B—C8B—C9B109.90 (14)
C6A—O6A—H6A109.5O9B—C8B—C7B108.50 (13)
C7A—O7A—C11A114.15 (13)C9B—C8B—C7B110.38 (14)
C7A—O8A—Na1A114.11 (10)O9B—C8B—H8E109.3
C7A—O8A—H8A109.6C9B—C8B—H8E109.3
Na1A—O8A—H8A114.7C7B—C8B—H8E109.3
C8A—O9A—Na1A113.84 (10)O10B—C9B—C10B108.10 (14)
C8A—O9A—H9A109.4O10B—C9B—C8B110.79 (14)
Na1A—O9A—H9A136.4C10B—C9B—C8B109.38 (14)
C9A—O10A—H10A109.5O10B—C9B—H9E109.5
C10A—O11A—Na1Aii146.21 (11)C10B—C9B—H9E109.5
C10A—O11A—H11A107.0C8B—C9B—H9E109.5
Na1Aii—O11A—H11A106.8O11B—C10B—C9B110.03 (13)
C12A—O12A—H12A109.5O11B—C10B—C11B108.78 (13)
O2A—C1A—O1A112.30 (14)C9B—C10B—C11B110.56 (14)
O2A—C1A—C2A107.14 (14)O11B—C10B—H10E109.1
O1A—C1A—C2A109.83 (14)C9B—C10B—H10E109.1
O2A—C1A—H1D109.2C11B—C10B—H10E109.1
O1A—C1A—H1D109.2O7B—C11B—C12B107.85 (14)
C2A—C1A—H1D109.2O7B—C11B—C10B109.63 (13)
O3A—C2A—C3A109.83 (14)C12B—C11B—C10B112.35 (14)
O3A—C2A—C1A108.74 (13)O7B—C11B—H11E109.0
C3A—C2A—C1A109.97 (14)C12B—C11B—H11E109.0
O3A—C2A—H2D109.4C10B—C11B—H11E108.9
C3A—C2A—H2D109.4O12B—C12B—C11B112.78 (15)
C1A—C2A—H2D109.4O12B—C12B—H12F109.0
O4A—C3A—C4A108.28 (13)C11B—C12B—H12F109.0
O4A—C3A—C2A110.05 (14)O12B—C12B—H12G109.0
C4A—C3A—C2A110.02 (13)C11B—C12B—H12G109.0
O4A—C3A—H3D109.5H12F—C12B—H12G107.8
C4A—C3A—H3D109.5O5Cv—Na1C—O9C120.55 (6)
C2A—C3A—H3D109.5O5Cv—Na1C—O2C129.99 (6)
O5A—C4A—C3A110.83 (13)O9C—Na1C—O2C93.99 (5)
O5A—C4A—C5A108.95 (14)O5Cv—Na1C—O3C102.86 (6)
C3A—C4A—C5A110.45 (13)O9C—Na1C—O3C131.69 (7)
O5A—C4A—H4D108.9O2C—Na1C—O3C70.42 (5)
C3A—C4A—H4D108.9O5Cv—Na1C—O11Cvi73.36 (5)
C5A—C4A—H4D108.9O9C—Na1C—O11Cvi79.31 (5)
O1A—C5A—C6A108.33 (14)O2C—Na1C—O11Cvi79.83 (5)
O1A—C5A—C4A108.95 (13)O3C—Na1C—O11Cvi137.05 (6)
C6A—C5A—C4A112.29 (14)O5Cv—Na1C—O8C102.51 (6)
O1A—C5A—H5D109.0O9C—Na1C—O8C69.07 (5)
C6A—C5A—H5D109.1O2C—Na1C—O8C124.36 (6)
C4A—C5A—H5D109.1O3C—Na1C—O8C82.53 (5)
O6A—C6A—C5A113.01 (15)O11Cvi—Na1C—O8C140.42 (6)
O6A—C6A—H6D109.0C1C—O1C—C5C114.49 (13)
C5A—C6A—H6D109.0C1C—O2C—Na1C114.60 (11)
O6A—C6A—H6E109.0C1C—O2C—H2C109.3
C5A—C6A—H6E109.0Na1C—O2C—H2C109.0
H6D—C6A—H6E107.8C2C—O3C—Na1C113.20 (10)
O8A—C7A—O7A111.84 (14)C2C—O3C—H3C109.6
O8A—C7A—C8A107.98 (14)Na1C—O3C—H3C137.0
O7A—C7A—C8A109.99 (14)C3C—O4C—H4C109.5
O8A—C7A—H7D109.0C4C—O5C—Na1Cvi145.32 (12)
O7A—C7A—H7D109.0C4C—O5C—H5C107.1
C8A—C7A—H7D109.0Na1Cvi—O5C—H5C107.5
O9A—C8A—C9A111.21 (15)C6C—O6C—H6C109.5
O9A—C8A—C7A107.96 (14)C7C—O7C—C11C113.51 (13)
C9A—C8A—C7A110.37 (14)C7C—O8C—Na1C113.85 (10)
O9A—C8A—H8D109.1C7C—O8C—H8C109.3
C9A—C8A—H8D109.1Na1C—O8C—H8C121.6
C7A—C8A—H8D109.1C8C—O9C—Na1C116.28 (10)
O10A—C9A—C8A109.15 (14)C8C—O9C—H9C109.4
O10A—C9A—C10A109.95 (15)Na1C—O9C—H9C133.9
C8A—C9A—C10A109.42 (14)C9C—O10C—H10C109.5
O10A—C9A—H9D109.4C10C—O11C—Na1Cv146.64 (11)
C8A—C9A—H9D109.4C10C—O11C—H11C104.9
C10A—C9A—H9D109.4Na1Cv—O11C—H11C103.5
O11A—C10A—C9A110.42 (14)C12C—O12C—H12C109.5
O11A—C10A—C11A107.41 (14)O2C—C1C—O1C111.42 (15)
C9A—C10A—C11A111.10 (14)O2C—C1C—C2C107.13 (14)
O11A—C10A—H10D109.3O1C—C1C—C2C109.55 (14)
C9A—C10A—H10D109.3O2C—C1C—H1F109.6
C11A—C10A—H10D109.3O1C—C1C—H1F109.6
O7A—C11A—C12A107.79 (14)C2C—C1C—H1F109.6
O7A—C11A—C10A109.47 (13)O3C—C2C—C3C110.71 (15)
C12A—C11A—C10A113.19 (14)O3C—C2C—C1C108.03 (14)
O7A—C11A—H11D108.8C3C—C2C—C1C110.01 (14)
C12A—C11A—H11D108.8O3C—C2C—H2F109.4
C10A—C11A—H11D108.8C3C—C2C—H2F109.4
O12A—C12A—C11A112.48 (16)C1C—C2C—H2F109.4
O12A—C12A—H12D109.1O4C—C3C—C2C109.80 (14)
C11A—C12A—H12D109.1O4C—C3C—C4C109.38 (15)
O12A—C12A—H12E109.1C2C—C3C—C4C109.62 (14)
C11A—C12A—H12E109.1O4C—C3C—H3F109.3
H12D—C12A—H12E107.8C2C—C3C—H3F109.3
O5Biii—Na1B—O9B121.01 (6)C4C—C3C—H3F109.3
O5Biii—Na1B—O3B102.33 (6)O5C—C4C—C3C110.78 (14)
O9B—Na1B—O3B130.86 (6)O5C—C4C—C5C106.77 (14)
O5Biii—Na1B—O2B134.78 (6)C3C—C4C—C5C111.54 (14)
O9B—Na1B—O2B92.35 (5)O5C—C4C—H4F109.2
O3B—Na1B—O2B68.99 (5)C3C—C4C—H4F109.2
O5Biii—Na1B—O11Biv73.49 (5)C5C—C4C—H4F109.2
O9B—Na1B—O11Biv79.43 (5)O1C—C5C—C6C108.13 (14)
O3B—Na1B—O11Biv138.99 (6)O1C—C5C—C4C109.18 (14)
O2B—Na1B—O11Biv85.16 (6)C6C—C5C—C4C113.07 (15)
O5Biii—Na1B—O8B96.95 (5)O1C—C5C—H5F108.8
O9B—Na1B—O8B69.66 (5)C6C—C5C—H5F108.8
O3B—Na1B—O8B84.11 (6)C4C—C5C—H5F108.8
O2B—Na1B—O8B124.61 (6)O6C—C6C—C5C112.82 (17)
O11Biv—Na1B—O8B136.67 (6)O6C—C6C—H6H109.0
C1B—O1B—C5B113.80 (13)C5C—C6C—H6H109.0
C1B—O2B—Na1B115.56 (11)O6C—C6C—H6I109.0
C1B—O2B—H2B109.6C5C—C6C—H6I109.0
Na1B—O2B—H2B112.8H6H—C6C—H6I107.8
C2B—O3B—Na1B114.17 (11)O8C—C7C—O7C112.14 (14)
C2B—O3B—H3B109.4O8C—C7C—C8C107.53 (13)
Na1B—O3B—H3B136.2O7C—C7C—C8C109.27 (13)
C3B—O4B—H4B109.5O8C—C7C—H7F109.3
C4B—O5B—Na1Biv146.74 (11)O7C—C7C—H7F109.3
C4B—O5B—H5B105.5C8C—C7C—H7F109.3
Na1Biv—O5B—H5B105.5O9C—C8C—C7C108.46 (13)
C6B—O6B—H6B109.5O9C—C8C—C9C109.71 (14)
C7B—O7B—C11B113.19 (12)C7C—C8C—C9C110.53 (13)
C7B—O8B—Na1B113.17 (10)O9C—C8C—H8F109.4
C7B—O8B—H8B123.4C7C—C8C—H8F109.4
Na1B—O8B—H8B123.4C9C—C8C—H8F109.4
C8B—O9B—Na1B115.71 (10)O10C—C9C—C10C108.00 (14)
C8B—O9B—H9B109.6O10C—C9C—C8C109.77 (14)
Na1B—O9B—H9B133.3C10C—C9C—C8C109.51 (13)
C9B—O10B—H10B109.5O10C—C9C—H9F109.8
C10B—O11B—Na1Biii145.66 (11)C10C—C9C—H9F109.8
C10B—O11B—H11B109.6C8C—C9C—H9F109.8
Na1Biii—O11B—H11B104.7O11C—C10C—C9C110.19 (13)
C12B—O12B—H12B109.5O11C—C10C—C11C108.54 (14)
O2B—C1B—O1B111.69 (15)C9C—C10C—C11C110.39 (14)
O2B—C1B—C2B107.40 (14)O11C—C10C—H10F109.2
O1B—C1B—C2B109.54 (14)C9C—C10C—H10F109.2
O2B—C1B—H1E109.4C11C—C10C—H10F109.2
O1B—C1B—H1E109.4O7C—C11C—C12C107.80 (14)
C2B—C1B—H1E109.4O7C—C11C—C10C109.40 (13)
O3B—C2B—C1B107.24 (14)C12C—C11C—C10C112.27 (14)
O3B—C2B—C3B111.27 (15)O7C—C11C—H11F109.1
C1B—C2B—C3B110.44 (14)C12C—C11C—H11F109.1
O3B—C2B—H2E109.3C10C—C11C—H11F109.1
C1B—C2B—H2E109.3O12C—C12C—C11C112.57 (15)
C3B—C2B—H2E109.3O12C—C12C—H12H109.1
O4B—C3B—C2B109.15 (14)C11C—C12C—H12H109.1
O4B—C3B—C4B110.08 (15)O12C—C12C—H12I109.1
C2B—C3B—C4B109.82 (14)C11C—C12C—H12I109.1
O4B—C3B—H3E109.3H12H—C12C—H12I107.8
C2B—C3B—H3E109.3
O9A—Na1A—O2A—C1A−120.96 (12)O4B—C3B—C4B—C5B174.19 (14)
O11Ai—Na1A—O2A—C1A139.58 (12)C2B—C3B—C4B—C5B53.99 (18)
O5Aii—Na1A—O2A—C1A63.79 (15)C1B—O1B—C5B—C6B−176.84 (15)
O3A—Na1A—O2A—C1A18.66 (11)C1B—O1B—C5B—C4B60.01 (18)
O8A—Na1A—O2A—C1A−60.15 (13)O5B—C4B—C5B—O1B−177.07 (13)
O9A—Na1A—O3A—C2A72.64 (14)C3B—C4B—C5B—O1B−55.55 (18)
O11Ai—Na1A—O3A—C2A−74.62 (13)O5B—C4B—C5B—C6B62.84 (19)
O5Aii—Na1A—O3A—C2A−138.74 (12)C3B—C4B—C5B—C6B−175.64 (15)
O8A—Na1A—O3A—C2A138.79 (12)O1B—C5B—C6B—O6B−67.08 (19)
O2A—Na1A—O3A—C2A13.12 (11)C4B—C5B—C6B—O6B53.8 (2)
O9A—Na1A—O8A—C7A14.24 (11)Na1B—O8B—C7B—O7B−167.86 (10)
O11Ai—Na1A—O8A—C7A100.11 (13)Na1B—O8B—C7B—C8B−47.14 (15)
O5Aii—Na1A—O8A—C7A160.32 (12)C11B—O7B—C7B—O8B58.45 (18)
O3A—Na1A—O8A—C7A−119.20 (12)C11B—O7B—C7B—C8B−61.09 (18)
O2A—Na1A—O8A—C7A−52.99 (13)Na1B—O9B—C8B—C9B83.07 (14)
O11Ai—Na1A—O9A—C8A−113.77 (12)Na1B—O9B—C8B—C7B−37.71 (16)
O5Aii—Na1A—O9A—C8A−36.75 (16)O8B—C7B—C8B—O9B55.43 (17)
O3A—Na1A—O9A—C8A93.99 (13)O7B—C7B—C8B—O9B177.51 (13)
O8A—Na1A—O9A—C8A17.96 (12)O8B—C7B—C8B—C9B−65.06 (17)
O2A—Na1A—O9A—C8A147.85 (12)O7B—C7B—C8B—C9B57.03 (18)
Na1A—O2A—C1A—O1A−164.95 (10)O9B—C8B—C9B—O10B66.81 (17)
Na1A—O2A—C1A—C2A−44.28 (16)C7B—C8B—C9B—O10B−173.55 (13)
C5A—O1A—C1A—O2A57.76 (19)O9B—C8B—C9B—C10B−174.12 (13)
C5A—O1A—C1A—C2A−61.35 (18)C7B—C8B—C9B—C10B−54.48 (18)
Na1A—O3A—C2A—C3A80.70 (14)Na1Biii—O11B—C10B—C9B−27.9 (3)
Na1A—O3A—C2A—C1A−39.69 (16)Na1Biii—O11B—C10B—C11B93.4 (2)
O2A—C1A—C2A—O3A54.06 (18)O10B—C9B—C10B—O11B−64.70 (18)
O1A—C1A—C2A—O3A176.29 (13)C8B—C9B—C10B—O11B174.57 (13)
O2A—C1A—C2A—C3A−66.23 (17)O10B—C9B—C10B—C11B175.12 (13)
O1A—C1A—C2A—C3A55.99 (18)C8B—C9B—C10B—C11B54.40 (18)
O3A—C2A—C3A—O4A67.34 (17)C7B—O7B—C11B—C12B−176.56 (14)
C1A—C2A—C3A—O4A−173.02 (13)C7B—O7B—C11B—C10B60.83 (17)
O3A—C2A—C3A—C4A−173.43 (13)O11B—C10B—C11B—O7B−177.59 (12)
C1A—C2A—C3A—C4A−53.80 (18)C9B—C10B—C11B—O7B−56.66 (17)
Na1Ai—O5A—C4A—C3A−27.8 (3)O11B—C10B—C11B—C12B62.51 (18)
Na1Ai—O5A—C4A—C5A93.9 (2)C9B—C10B—C11B—C12B−176.56 (14)
O4A—C3A—C4A—O5A−63.94 (18)O7B—C11B—C12B—O12B−68.48 (18)
C2A—C3A—C4A—O5A175.76 (14)C10B—C11B—C12B—O12B52.5 (2)
O4A—C3A—C4A—C5A175.23 (14)O5Cv—Na1C—O2C—C1C107.60 (13)
C2A—C3A—C4A—C5A54.93 (18)O9C—Na1C—O2C—C1C−116.03 (12)
C1A—O1A—C5A—C6A−175.84 (14)O3C—Na1C—O2C—C1C17.03 (11)
C1A—O1A—C5A—C4A61.74 (18)O11Cvi—Na1C—O2C—C1C165.59 (12)
O5A—C4A—C5A—O1A−179.34 (13)O8C—Na1C—O2C—C1C−48.74 (13)
C3A—C4A—C5A—O1A−57.39 (17)O5Cv—Na1C—O3C—C2C−112.48 (12)
O5A—C4A—C5A—C6A60.66 (18)O9C—Na1C—O3C—C2C93.14 (13)
C3A—C4A—C5A—C6A−177.39 (14)O2C—Na1C—O3C—C2C15.72 (11)
O1A—C5A—C6A—O6A−67.48 (19)O11Cvi—Na1C—O3C—C2C−33.19 (16)
C4A—C5A—C6A—O6A52.9 (2)O8C—Na1C—O3C—C2C146.33 (12)
Na1A—O8A—C7A—O7A−162.57 (10)O5Cv—Na1C—O8C—C7C135.81 (11)
Na1A—O8A—C7A—C8A−41.42 (16)O9C—Na1C—O8C—C7C17.61 (11)
C11A—O7A—C7A—O8A59.60 (19)O2C—Na1C—O8C—C7C−62.54 (13)
C11A—O7A—C7A—C8A−60.38 (18)O3C—Na1C—O8C—C7C−122.60 (12)
Na1A—O9A—C8A—C9A76.24 (15)O11Cvi—Na1C—O8C—C7C56.88 (15)
Na1A—O9A—C8A—C7A−44.98 (16)O5Cv—Na1C—O9C—C8C−78.21 (13)
O8A—C7A—C8A—O9A56.58 (18)O2C—Na1C—O9C—C8C139.66 (12)
O7A—C7A—C8A—O9A178.88 (13)O3C—Na1C—O9C—C8C72.47 (14)
O8A—C7A—C8A—C9A−65.16 (18)O11Cvi—Na1C—O9C—C8C−141.48 (12)
O7A—C7A—C8A—C9A57.14 (18)O8C—Na1C—O9C—C8C14.28 (11)
O9A—C8A—C9A—O10A65.19 (18)Na1C—O2C—C1C—O1C−164.10 (10)
C7A—C8A—C9A—O10A−175.01 (14)Na1C—O2C—C1C—C2C−44.29 (16)
O9A—C8A—C9A—C10A−174.45 (13)C5C—O1C—C1C—O2C56.97 (19)
C7A—C8A—C9A—C10A−54.66 (18)C5C—O1C—C1C—C2C−61.39 (19)
Na1Aii—O11A—C10A—C9A−75.4 (2)Na1C—O3C—C2C—C3C77.26 (15)
Na1Aii—O11A—C10A—C11A45.9 (3)Na1C—O3C—C2C—C1C−43.25 (16)
O10A—C9A—C10A—O11A−66.95 (18)O2C—C1C—C2C—O3C57.24 (18)
C8A—C9A—C10A—O11A173.19 (14)O1C—C1C—C2C—O3C178.24 (14)
O10A—C9A—C10A—C11A173.98 (14)O2C—C1C—C2C—C3C−63.71 (18)
C8A—C9A—C10A—C11A54.12 (18)O1C—C1C—C2C—C3C57.28 (18)
C7A—O7A—C11A—C12A−177.39 (14)O3C—C2C—C3C—O4C66.14 (18)
C7A—O7A—C11A—C10A59.09 (18)C1C—C2C—C3C—O4C−174.54 (14)
O11A—C10A—C11A—O7A−175.80 (13)O3C—C2C—C3C—C4C−173.68 (14)
C9A—C10A—C11A—O7A−54.94 (17)C1C—C2C—C3C—C4C−54.35 (18)
O11A—C10A—C11A—C12A63.94 (18)Na1Cvi—O5C—C4C—C3C−82.3 (2)
C9A—C10A—C11A—C12A−175.20 (14)Na1Cvi—O5C—C4C—C5C39.3 (3)
O7A—C11A—C12A—O12A−67.61 (19)O4C—C3C—C4C—O5C−67.22 (18)
C10A—C11A—C12A—O12A53.6 (2)C2C—C3C—C4C—O5C172.33 (14)
O5Biii—Na1B—O2B—C1B99.63 (14)O4C—C3C—C4C—C5C173.99 (14)
O9B—Na1B—O2B—C1B−120.26 (12)C2C—C3C—C4C—C5C53.55 (18)
O3B—Na1B—O2B—C1B13.02 (11)C1C—O1C—C5C—C6C−177.14 (15)
O11Biv—Na1B—O2B—C1B160.56 (12)C1C—O1C—C5C—C4C59.47 (18)
O8B—Na1B—O2B—C1B−53.49 (14)O5C—C4C—C5C—O1C−175.59 (14)
O5Biii—Na1B—O3B—C2B−113.75 (12)C3C—C4C—C5C—O1C−54.45 (18)
O9B—Na1B—O3B—C2B93.85 (13)O5C—C4C—C5C—C6C63.99 (19)
O2B—Na1B—O3B—C2B19.76 (12)C3C—C4C—C5C—C6C−174.86 (15)
O11Biv—Na1B—O3B—C2B−34.83 (17)O1C—C5C—C6C—O6C−65.9 (2)
O8B—Na1B—O3B—C2B150.40 (12)C4C—C5C—C6C—O6C55.1 (2)
O5Biii—Na1B—O8B—C7B141.71 (11)Na1C—O8C—C7C—O7C−163.83 (10)
O9B—Na1B—O8B—C7B21.16 (11)Na1C—O8C—C7C—C8C−43.68 (15)
O3B—Na1B—O8B—C7B−116.54 (11)C11C—O7C—C7C—O8C57.97 (18)
O2B—Na1B—O8B—C7B−57.15 (13)C11C—O7C—C7C—C8C−61.16 (18)
O11Biv—Na1B—O8B—C7B68.46 (14)Na1C—O9C—C8C—C7C−41.39 (16)
O5Biii—Na1B—O9B—C8B−75.30 (13)Na1C—O9C—C8C—C9C79.42 (15)
O3B—Na1B—O9B—C8B72.82 (14)O8C—C7C—C8C—O9C55.19 (17)
O2B—Na1B—O9B—C8B136.78 (12)O7C—C7C—C8C—O9C177.13 (13)
O11Biv—Na1B—O9B—C8B−138.59 (12)O8C—C7C—C8C—C9C−65.12 (17)
O8B—Na1B—O9B—C8B10.55 (11)O7C—C7C—C8C—C9C56.82 (18)
Na1B—O2B—C1B—O1B−160.91 (10)O9C—C8C—C9C—O10C67.30 (17)
Na1B—O2B—C1B—C2B−40.78 (16)C7C—C8C—C9C—O10C−173.15 (13)
C5B—O1B—C1B—O2B57.95 (19)O9C—C8C—C9C—C10C−174.30 (14)
C5B—O1B—C1B—C2B−60.91 (18)C7C—C8C—C9C—C10C−54.74 (18)
Na1B—O3B—C2B—C1B−47.04 (16)Na1Cv—O11C—C10C—C9C−17.0 (3)
Na1B—O3B—C2B—C3B73.84 (15)Na1Cv—O11C—C10C—C11C104.0 (2)
O2B—C1B—C2B—O3B56.69 (18)O10C—C9C—C10C—O11C−66.05 (18)
O1B—C1B—C2B—O3B178.18 (14)C8C—C9C—C10C—O11C174.44 (14)
O2B—C1B—C2B—C3B−64.71 (18)O10C—C9C—C10C—C11C174.07 (14)
O1B—C1B—C2B—C3B56.78 (18)C8C—C9C—C10C—C11C54.57 (18)
O3B—C2B—C3B—O4B65.90 (18)C7C—O7C—C11C—C12C−176.51 (14)
C1B—C2B—C3B—O4B−175.12 (14)C7C—O7C—C11C—C10C61.14 (18)
O3B—C2B—C3B—C4B−173.34 (14)O11C—C10C—C11C—O7C−177.64 (13)
C1B—C2B—C3B—C4B−54.36 (18)C9C—C10C—C11C—O7C−56.78 (17)
Na1Biv—O5B—C4B—C3B−76.5 (2)O11C—C10C—C11C—C12C62.72 (18)
Na1Biv—O5B—C4B—C5B45.2 (3)C9C—C10C—C11C—C12C−176.41 (14)
O4B—C3B—C4B—O5B−66.17 (18)O7C—C11C—C12C—O12C−68.07 (19)
C2B—C3B—C4B—O5B173.62 (13)C10C—C11C—C12C—O12C52.5 (2)

Symmetry codes: (i) −y+1, xy+1, z+1/3; (ii) −x+y, −x+1, z−1/3; (iii) −y+2, xy+1, z+1/3; (iv) −x+y+1, −x+2, z−1/3; (v) −x+y+1, −x+1, z−1/3; (vi) −y+1, xy, z+1/3.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2A—H2A···O12Bvii0.851.792.630 (3)172
O2B—H2B···O12Cviii0.851.792.640 (3)174
O2C—H2C···O6Aix0.851.822.665 (3)176
O3A—H3A···O1B0.851.912.753 (2)169
O3B—H3B···O1Cvi0.851.902.727 (2)163
O3C—H3C···O7Ax0.851.942.755 (2)161
O4A—H4A···Cl2xi0.822.343.158 (2)174
O4B—H4B···Cl3xii0.822.453.270 (2)173
O4C—H4C···Cl10.822.473.256 (2)161
O5A—H5A···Cl2xiii0.832.353.151 (1)162
O5B—H5B···O10Bix0.851.982.828 (2)175
O5C—H5C···O10Cxiv0.851.942.773 (2)165
O6A—H6A···Cl2xiii0.822.333.144 (2)174
O6B—H6B···Cl3ii0.822.413.220 (2)170
O6C—H6C···O8Bv0.822.332.696 (3)108
O8A—H8A···O6B0.851.882.726 (3)177
O8B—H8B···O6Cvi0.932.102.696 (3)121
O8C—H8C···O12Ax0.851.852.699 (2)173
O9A—H9A···O7Bvii0.851.972.786 (3)162
O9B—H9B···O7Cviii0.851.972.798 (2)166
O9C—H9C···O1Aix0.851.942.775 (2)168
O10A—H10A···Cl2i0.822.513.245 (2)150
O10B—H10B···Cl3xv0.822.333.147 (2)171
O10C—H10C···Cl1v0.822.483.144 (2)139
O11A—H11A···O4Avii0.852.032.819 (3)155
O11B—H11B···Cl3xi0.812.433.159 (2)150
O11C—H11C···Cl1xvi0.832.363.166 (2)164
O12A—H12A···Cl20.822.453.229 (2)159
O12B—H12B···Cl3xi0.822.373.135 (2)156
O12C—H12C···Cl1xvi0.822.323.138 (2)173

Symmetry codes: (vii) −y+1, xy+1, z−2/3; (viii) x, y+1, z+1; (ix) −y+2, xy+1, z−2/3; (vi) −y+1, xy, z+1/3; (x) x, y−1, z; (xi) −x+y, −x+1, z+2/3; (xii) x+1, y, z; (xiii) x, y, z+1; (xiv) −x+y+1, −x+1, z+2/3; (ii) −x+y, −x+1, z−1/3; (v) −x+y+1, −x+1, z−1/3; (i) −y+1, xy+1, z+1/3; (xv) −y+2, xy+2, z+1/3; (xvi) −y+1, xy, z−2/3.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2906).

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