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The title compound, 4Na+·C24H12O16S84−·14H2O (Na4TCAS·14H2O), was found to crystallize in the triclinic space group P\overline 1. The X-ray structure revealed that the centrosymmetric TCAS4− anion adopts the 1,2-alternate conformation. The sodium cations are surrounded by five or six O atoms in the crystal structure. All sodium ions form centrosymmetric aqua-bridged dimers, Na(μ-H2O)2Na, which are also coordinated by sulfonate O atoms and contribute to the formation of a three-dimensional network. The compound exists in the solid state as layers of anionic thia­calixarenes, alternating with inorganic layers that contain sodium cations and water mol­ecules. Intercalation of metal ions into the solid-state layered structure was observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009784/cv6187sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009784/cv6187Isup2.hkl
Contains datablock I

CCDC reference: 214780

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.031
  • wR factor = 0.091
  • Data-to-parameter ratio = 11.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 4678 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5098 Completeness (_total/calc) 91.76% Alert C: < 95% complete PLAT_728 Alert C D-H..A Calc 144.94, Rep 146.00, Dev. 1.06 Deg. O5 -H4 -O15 1.555 1.555 1.455 General Notes
ABSTY_01 Extra text has been found in the _exptl_absorpt_correction_type field, which should be only a single keyword. A literature citation should be included in the _exptl_absorpt_process_details field.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

The title compound, (I) (Na4TCAS.14H2O), gives the first crystal structure of Na4TCAS without organic solvents as guest molecules, while crystal structures of Na4TCAS with acetone or 1,4-dioxane (Iki et al., 2001) and analogue of thiacalix[4]arenetetrasulfonate, Na5[S8C24O24H11]·EtOH·9H2O (Iki et al., 2002), are known.

A view of the TCAS4− anion is shown in Fig. 1. Selected bond distances and angles are tabulated in Table 1. The TCAS4− molecule adopted the 1,2-alternate conformation. The center of symmetry resides on the mid-point of two S atoms (S1 and S1*). The bond distances and angles in the TCAS4− molecule are similar to those observed in Na4[C24H12O16S8]·2C4H8O2·9H2O (Iki et al., 2001).

The environments around Na1 and Na2 atoms are different. The Na1 atom is coordinated by six O atoms (O2 and O6ii from sulfonate O atoms, and O9, O10, O11 and O11iii from water molecules; see Table 1 for symmetry codes) in a distorted octahedral manner. The NaO6 polyhedra share a common edge. The bridging positions are occupied by water molecules (O11 and O11iii). The center of symmetry resides on the midpoint of two aqua-bridges. The Na1···O11 [2.346 (2) Å] and Na1···O11iii [2.474 (2) Å] distances are in the range of the usual Na···µ-H2O distances (2.35–2.48 Å) [for examples, see Dressick et al. (2000) and Achour et al. (1998)]. The Na2 atom is coordinated by five O atoms (O3 and O8iv from sulfonate O atoms, and O12, O13 and O13v from water molecules; see Table 1 for symmetry codes) in a distorted trigonalbipyramidal manner. The NaO5 polyhedra share a common edge. The bridging positions are occupied by water molecules (O13 and O13v). The center of symmetry resides on the mid-point of two aqua bridges. The Na2···O13 [2.388 (2) Å] and Na2···O13v [2.388 (2) Å] distances are in the usual range for Na···µ-H2O distances (2.27–2.44 Å) (for examples, see Hauptmann et al. (1999) and Jeon et al. (1996)].

The crystal structure of (I), viewed along the b axis, is shown in Fig. 2. Since sulfonate O atoms are coordinated to Na+ cations, TCAS4− molecules are further connected by sodium aqua dimmers, Na–(µ-H2O)2–Na, forming a three-dimensional network.

The compound exists in the solid state as layers of anionic thiacalixarenes in the 1,2-alternate configuration. These layers alternate with inorganic layers that contain sodium cations and water molecules. The overall structure bears a close resemblance to those found in clay minerals. This similarity has also been reported in studies of calixarene compounds (Atwood et al., 1988; Coleman et al., 1988).

Several metal (Fe, Co, Ni, Cu, Zn) complexes of water-soluble thiacalix[4]arenetetrasulfonate have been prepared by the incorporation of the metal ions into the solid-state layered structure. There have also been several reports of the intercalation of metal ions with water-soluble calix[4]arenes (Atwood et al., 1992). X-ray structure analyses of the metal complexes of water-soluble thiacalix[4]arenetetrasulfonate are in progress.

Experimental top

A sample of sodium thiacalix[4]arenetetrasulfonate (Na4TCAS), was obtained from Cosmo Oil Co. Ltd. Crystals suitable for single-crystal X-ray diffraction were recrystallized by adding sodium chloride to a water solution of Na4(TCAS).

Refinement top

The positions of all the H atoms were initially located from a difference map. The coordinate parameters for all H atoms are refined. All water O—H distances and H—O—H angles were restrained to be 0.9 Å and 104°, respectively. The isotropic displacement parameters for all H atoms were fixed at 1.2 times the value of the equivalent isotropic displacement parameter of their carrier atom.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CrystalStructure (Rigaku/MSC 2001); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC 2001).

Figures top
[Figure 1] Fig. 1. ORTEP-3 drawing of the TCAS4− anion with the atom-numbering scheme. Displacement ellipsoids are drawn at the 80% probability level and H atoms are shown as spheres of arbitrary radii. Atoms marked with an asterisk are related to those without an asterisk by a center of symmetry.
[Figure 2] Fig. 2. Projection of the structure of compound (I) along the b axis. The C, O, Na and S atoms are drawn in black, red, blue and yellow, respectively. Non-coordinated crystal water molecules have been omitted for clarity.
(I) top
Crystal data top
4Na+·C24H12O16S84·14H2OZ = 1
Mr = 1157.00F(000) = 596.00
Triclinic, P1Dx = 1.730 Mg m3
a = 8.2974 (7) ÅMo Kα radiation, λ = 0.7107 Å
b = 8.8446 (6) ÅCell parameters from 4591 reflections
c = 15.789 (1) Åθ = 2.5–27.5°
α = 95.743 (4)°µ = 0.54 mm1
β = 102.490 (2)°T = 93 K
γ = 97.897 (4)°Plate, colorless
V = 1110.4 (1) Å30.30 × 0.20 × 0.10 mm
Data collection top
Rigaku R-AXIS-IV
diffractometer
3541 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.018
ω scansθmax = 27.5°
Absorption correction: multi-scan (higashi, 1995)
?
h = 1010
Tmin = 0.848, Tmax = 0.948k = 1111
8541 measured reflectionsl = 2020
4678 independent reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.031 w = 1/[0.001Fo2 + σ2(Fo) + 0.5]/(4Fo2)
wR(F2) = 0.091(Δ/σ)max < 0.001
S = 0.84Δρmax = 0.46 e Å3
4233 reflectionsΔρmin = 0.54 e Å3
358 parameters
Crystal data top
4Na+·C24H12O16S84·14H2Oγ = 97.897 (4)°
Mr = 1157.00V = 1110.4 (1) Å3
Triclinic, P1Z = 1
a = 8.2974 (7) ÅMo Kα radiation
b = 8.8446 (6) ŵ = 0.54 mm1
c = 15.789 (1) ÅT = 93 K
α = 95.743 (4)°0.30 × 0.20 × 0.10 mm
β = 102.490 (2)°
Data collection top
Rigaku R-AXIS-IV
diffractometer
4678 independent reflections
Absorption correction: multi-scan (higashi, 1995)
?
3541 reflections with F2 > 2σ(F2)
Tmin = 0.848, Tmax = 0.948Rint = 0.018
8541 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031358 parameters
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 0.84Δρmax = 0.46 e Å3
4233 reflectionsΔρmin = 0.54 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.43010 (7)0.27994 (7)0.45382 (4)0.0055 (1)
S20.16572 (7)0.33281 (7)0.45344 (4)0.0051 (1)
S30.21040 (7)0.09787 (7)0.14849 (4)0.0053 (1)
S40.43052 (7)0.52342 (7)0.78607 (4)0.0055 (1)
Na10.5968 (1)0.0805 (1)0.11192 (6)0.0091 (2)
Na20.1760 (1)0.5027 (1)0.08505 (6)0.0102 (2)
O10.3103 (2)0.0041 (2)0.5319 (1)0.0080 (4)
O20.3151 (2)0.0318 (2)0.1264 (1)0.0086 (4)
O30.2526 (2)0.2459 (2)0.1205 (1)0.0096 (4)
O40.0314 (2)0.0916 (2)0.1168 (1)0.0105 (4)
O50.0644 (2)0.2550 (2)0.4269 (1)0.0079 (4)
O60.3848 (2)0.6765 (2)0.7965 (1)0.0105 (4)
O70.3704 (2)0.4248 (2)0.8457 (1)0.0108 (5)
O80.6086 (2)0.5273 (2)0.7907 (1)0.0096 (4)
O90.8835 (2)0.1779 (2)0.1251 (1)0.0127 (5)
O100.7461 (2)0.0932 (2)0.2088 (1)0.0134 (5)
O110.4993 (2)0.1736 (2)0.0206 (1)0.0108 (5)
O120.2069 (2)0.7417 (2)0.0265 (1)0.0107 (4)
O130.1253 (2)0.4631 (2)0.0651 (1)0.0114 (5)
O140.1040 (2)0.3651 (2)0.2638 (1)0.0136 (5)
O150.7472 (2)0.1531 (2)0.3372 (1)0.0101 (4)
C10.2861 (3)0.0281 (3)0.4445 (1)0.0057 (6)
C20.2199 (3)0.1744 (3)0.3970 (2)0.0062 (6)
C30.2034 (3)0.1983 (3)0.3067 (2)0.0072 (6)
C40.2483 (3)0.0743 (3)0.2637 (2)0.0060 (6)
C50.3118 (3)0.0708 (3)0.3097 (2)0.0063 (6)
C60.3312 (3)0.0948 (3)0.3997 (2)0.0054 (6)
C70.1421 (3)0.3105 (3)0.5108 (2)0.0060 (6)
C80.0573 (3)0.3548 (3)0.5748 (2)0.0056 (6)
C90.1484 (3)0.4215 (3)0.6580 (2)0.0069 (6)
C100.3220 (3)0.4378 (3)0.6790 (2)0.0065 (6)
C110.4065 (3)0.3875 (3)0.6173 (2)0.0060 (6)
C120.3166 (3)0.3260 (3)0.5330 (2)0.0054 (6)
H10.2850.0830.5540.0100*
H20.1570.3010.2790.0086*
H30.3450.1610.2800.0073*
H40.0380.2440.4190.0095*
H50.0960.4550.7010.0083*
H60.5280.4020.6360.0075*
H70.9380.1010.1110.0162*
H80.9550.2350.1720.0162*
H90.8420.0920.1910.0168*
H100.7000.1930.2000.0169*
H110.5540.2180.0580.0143*
H120.4270.2360.0120.0144*
H130.2340.8120.0620.0126*
H140.1210.7930.0160.0127*
H150.1930.5020.0960.0150*
H160.1390.3630.0710.0149*
H170.1120.3430.31880.0168*
H180.2110.3890.2600.0169*
H190.6980.2150.3020.0126*
H200.7420.0660.3020.0125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0046 (3)0.0053 (3)0.0066 (3)0.0015 (2)0.0032 (2)0.0003 (2)
S20.0031 (3)0.0056 (3)0.0067 (3)0.0002 (2)0.0015 (2)0.0022 (2)
S30.0059 (3)0.0055 (3)0.0049 (3)0.0003 (2)0.0022 (2)0.0009 (2)
S40.0050 (3)0.0062 (3)0.0048 (3)0.0001 (2)0.0008 (2)0.0004 (2)
Na10.0076 (5)0.0103 (5)0.0090 (5)0.0004 (4)0.0019 (4)0.0010 (4)
Na20.0114 (5)0.0080 (5)0.0104 (5)0.0014 (4)0.0010 (4)0.0007 (4)
O10.0119 (9)0.0058 (9)0.0061 (8)0.0013 (6)0.0032 (7)0.0008 (7)
O20.0107 (9)0.0078 (9)0.0078 (8)0.0001 (7)0.0039 (7)0.0023 (7)
O30.0147 (9)0.0054 (9)0.0105 (9)0.0030 (7)0.0066 (7)0.0003 (7)
O40.0062 (9)0.015 (1)0.0096 (9)0.0019 (7)0.0010 (7)0.0004 (7)
O50.0034 (8)0.013 (1)0.0053 (8)0.0015 (7)0.0001 (7)0.0024 (7)
O60.0129 (9)0.0073 (9)0.0094 (9)0.0026 (7)0.0006 (7)0.0014 (7)
O70.0133 (9)0.012 (1)0.0078 (8)0.0006 (7)0.0042 (7)0.0039 (7)
O80.0062 (9)0.014 (1)0.0078 (8)0.0000 (7)0.0004 (7)0.0004 (7)
O90.0097 (9)0.010 (1)0.019 (1)0.0021 (7)0.0046 (8)0.0010 (8)
O100.015 (1)0.009 (1)0.017 (1)0.0009 (7)0.0051 (8)0.0021 (8)
O110.0115 (9)0.012 (1)0.0109 (9)0.0034 (7)0.0063 (7)0.0035 (7)
O120.0110 (9)0.0098 (9)0.0100 (9)0.0022 (7)0.0009 (7)0.0018 (7)
O130.0145 (9)0.009 (1)0.0124 (9)0.0032 (7)0.0060 (7)0.0031 (7)
O140.0101 (9)0.020 (1)0.0121 (9)0.0030 (7)0.0038 (7)0.0044 (8)
O150.0118 (9)0.0103 (9)0.0074 (8)0.0009 (7)0.0007 (7)0.0013 (7)
C10.002 (1)0.010 (1)0.005 (1)0.0028 (8)0.0005 (8)0.0011 (9)
C20.005 (1)0.006 (1)0.009 (1)0.0008 (8)0.0038 (9)0.0029 (9)
C30.006 (1)0.006 (1)0.010 (1)0.0006 (9)0.0018 (9)0.000 (1)
C40.004 (1)0.007 (1)0.008 (1)0.0012 (8)0.0024 (9)0.0004 (9)
C50.005 (1)0.007 (1)0.007 (1)0.0005 (8)0.0021 (9)0.0026 (9)
C60.004 (1)0.005 (1)0.007 (1)0.0011 (8)0.0014 (9)0.0015 (9)
C70.006 (1)0.004 (1)0.008 (1)0.0001 (8)0.0012 (9)0.0018 (9)
C80.004 (1)0.004 (1)0.009 (1)0.0001 (8)0.0024 (9)0.0027 (9)
C90.007 (1)0.005 (1)0.009 (1)0.0001 (9)0.0039 (9)0.0017 (9)
C100.009 (1)0.003 (1)0.007 (1)0.0005 (8)0.0011 (9)0.0012 (9)
C110.004 (1)0.006 (1)0.009 (1)0.0006 (8)0.0025 (9)0.0029 (9)
C120.008 (1)0.002 (1)0.006 (1)0.0013 (8)0.0026 (9)0.0008 (9)
Geometric parameters (Å, º) top
S1—C61.770 (2)O15—H200.90
S1—C121.769 (2)C1—C21.404 (4)
S2—C21.792 (2)C1—C61.406 (3)
S2—C8i1.785 (2)C2—C31.395 (3)
S3—O21.4590 (18)C3—C41.396 (3)
S3—O31.4524 (18)C3—H20.96
S3—O41.4715 (18)C4—C51.383 (4)
S3—C41.763 (2)C5—C61.386 (3)
S4—O61.4590 (18)C5—H31.00
S4—O71.4635 (18)C7—C81.405 (3)
S4—O81.4593 (18)C7—C121.398 (3)
S4—C101.772 (2)C8—C91.393 (3)
O1—C11.347 (3)C9—C101.390 (3)
O1—H10.89C9—H50.92
O5—C71.350 (3)C10—C111.390 (3)
O5—H40.82C11—C121.392 (3)
O9—H70.90C11—H60.98
O9—H80.90Na1—O22.382 (2)
O10—H90.90Na1—O6ii2.434 (2)
O10—H100.90Na1—O92.373 (2)
O11—H110.90Na1—O102.531 (2)
O11—H120.90Na1—O112.347 (2)
O12—H130.90Na1—O11iii2.475 (2)
O12—H140.90Na2—O32.252 (2)
O13—H150.90Na2—O8iv2.402 (2)
O13—H160.898Na2—O122.292 (2)
O14—H170.90Na2—O132.387 (2)
O14—H180.90Na2—O13v2.423 (2)
O15—H190.90
C6—S1—C12105.61 (11)S1—C6—C1122.96 (18)
C2—S2—C8i100.93 (11)S1—C6—C5116.68 (19)
O2—S3—O3112.97 (11)C1—C6—C5120.1 (2)
O2—S3—O4111.40 (11)O5—C7—C8123.5 (2)
O3—S3—O4112.24 (11)O5—C7—C12117.0 (2)
O2—S3—C4106.15 (11)C8—C7—C12119.4 (2)
O3—S3—C4107.77 (11)S2i—C8—C9120.93 (18)
O4—S3—C4105.79 (11)S2i—C8—C7119.39 (18)
O6—S4—O7112.21 (11)C7—C8—C9119.6 (2)
O6—S4—O8113.01 (11)C8—C9—C10120.2 (2)
O7—S4—O8112.27 (11)C8—C9—H5121.4
O6—S4—C10105.68 (11)C10—C9—H5118.3
O7—S4—C10106.04 (11)S4—C10—C9118.03 (18)
O8—S4—C10107.00 (11)S4—C10—C11121.50 (18)
C1—O1—H1108.8C9—C10—C11120.5 (2)
S3—O2—Na1134.69 (11)C10—C11—C12119.5 (2)
S3—O3—Na2148.88 (12)C10—C11—H6116.6
C7—O5—H4112.6C12—C11—H6123.8
S4—O6—Na1ii149.38 (11)S1—C12—C7121.24 (18)
S4—O8—Na2iv127.9 (1)S1—C12—C11118.07 (18)
H7—O9—H8104.5C7—C12—C11120.6 (2)
H9—O10—H10104.5O2—Na1—O6ii85.21 (7)
Na1—O11—Na1iii96.80 (7)O2—Na1—O9166.16 (8)
H11—O11—H12104.5O2—Na1—O10104.32 (7)
H13—O12—H14104.5O2—Na1—O1188.49 (7)
Na2—O13—Na2v94.18 (7)O2—Na1—O11iii79.91 (7)
H15—O13—H16104.5O6ii—Na1—O981.28 (7)
H17—O14—H18104.5O9—Na1—O1076.97 (7)
H19—O15—H20104.5O9—Na1—O1195.64 (7)
O1—C1—C2124.1 (2)O9—Na1—O11iii113.65 (7)
O1—C1—C6116.6 (2)O10—Na1—O11155.35 (8)
C2—C1—C6119.3 (2)O11—Na1—O11iii83.20 (7)
S2—C2—C1119.80 (18)S3—Na2—O12165.22 (6)
S2—C2—C3119.92 (19)O3—Na2—O12153.71 (8)
C1—C2—C3120.2 (2)O3—Na2—O1387.89 (7)
C2—C3—C4119.4 (2)O3—Na2—O8iv87.03 (7)
C2—C3—H2114.9O3—Na2—O12153.71 (8)
C4—C3—H2125.7O3—Na2—O13v102.85 (7)
S3—C4—C3120.07 (19)O8iv—Na2—O1287.12 (7)
S3—C4—C5118.89 (19)O8iv—Na2—O13143.44 (7)
C3—C4—C5120.9 (2)O8iv—Na2—O13v130.56 (7)
C4—C5—C6120.1 (2)O12—Na2—O1381.71 (7)
C4—C5—H3121.7O12—Na2—O13v100.41 (7)
C6—C5—H3118.2O13—Na2—O13v85.82 (7)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y, z; (iv) x+1, y, z+1; (v) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O15iv0.901.952.693 (2)140
O5—H4···O15vi0.821.972.688 (2)146
O9—H7···O4vii0.901.972.831 (3)159
O9—H8···O14vii0.901.862.756 (3)176
O10—H9···O4vii0.902.163.033 (3)166
O10—H9···O90.902.713.055 (3)104
O10—H10···O7iv0.902.062.939 (3)165
O11—H11···O3iii0.902.062.894 (2)153
O11—H12···O12viii0.902.072.858 (3)146
O12—H13···O2ix0.901.912.796 (3)171
O12—H14···O4v0.901.902.793 (3)170
O13—H15···O7x0.902.042.935 (3)173
O13—H16···O9iii0.901.932.787 (3)159
O14—H17···O50.902.042.910 (3)163
Symmetry codes: (iii) x+1, y, z; (iv) x+1, y, z+1; (v) x, y1, z; (vi) x1, y, z; (vii) x+1, y, z; (viii) x, y+1, z; (ix) x, y1, z; (x) x, y1, z1.

Experimental details

Crystal data
Chemical formula4Na+·C24H12O16S84·14H2O
Mr1157.00
Crystal system, space groupTriclinic, P1
Temperature (K)93
a, b, c (Å)8.2974 (7), 8.8446 (6), 15.789 (1)
α, β, γ (°)95.743 (4), 102.490 (2), 97.897 (4)
V3)1110.4 (1)
Z1
Radiation typeMo Kα
µ (mm1)0.54
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerRigaku R-AXIS-IV
diffractometer
Absorption correctionMulti-scan (Higashi, 1995)
Tmin, Tmax0.848, 0.948
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
8541, 4678, 3541
Rint0.018
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.091, 0.84
No. of reflections4233
No. of parameters358
No. of restraints?
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.46, 0.54

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC 2001), SHELXS97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).

Selected geometric parameters (Å, º) top
S1—C61.770 (2)C5—C61.386 (3)
S1—C121.769 (2)C7—C81.405 (3)
S2—C21.792 (2)C7—C121.398 (3)
S2—C8i1.785 (2)C8—C91.393 (3)
S3—O21.4590 (18)C9—C101.390 (3)
S3—O31.4524 (18)C10—C111.390 (3)
S3—O41.4715 (18)C11—C121.392 (3)
S3—C41.763 (2)Na1—O22.382 (2)
S4—O61.4590 (18)Na1—O6ii2.434 (2)
S4—O71.4635 (18)Na1—O92.373 (2)
S4—O81.4593 (18)Na1—O102.531 (2)
S4—C101.772 (2)Na1—O112.347 (2)
O1—C11.347 (3)Na1—O11iii2.475 (2)
O5—C71.350 (3)Na2—O32.252 (2)
C1—C21.404 (4)Na2—O8iv2.402 (2)
C1—C61.406 (3)Na2—O122.292 (2)
C2—C31.395 (3)Na2—O132.387 (2)
C3—C41.396 (3)Na2—O13v2.423 (2)
C4—C51.383 (4)
C6—S1—C12105.61 (11)C8—C7—C12119.4 (2)
C2—S2—C8i100.93 (11)S2i—C8—C9120.93 (18)
O2—S3—O3112.97 (11)S2i—C8—C7119.39 (18)
O2—S3—O4111.40 (11)C7—C8—C9119.6 (2)
O3—S3—O4112.24 (11)C8—C9—C10120.2 (2)
O2—S3—C4106.15 (11)S4—C10—C9118.03 (18)
O3—S3—C4107.77 (11)S4—C10—C11121.50 (18)
O4—S3—C4105.79 (11)C9—C10—C11120.5 (2)
O6—S4—O7112.21 (11)C10—C11—C12119.5 (2)
O6—S4—O8113.01 (11)S1—C12—C7121.24 (18)
O7—S4—O8112.27 (11)S1—C12—C11118.07 (18)
O6—S4—C10105.68 (11)C7—C12—C11120.6 (2)
O7—S4—C10106.04 (11)O2—Na1—O6ii85.21 (7)
O8—S4—C10107.00 (11)O2—Na1—O9166.16 (8)
S3—O2—Na1134.69 (11)O2—Na1—O10104.32 (7)
S3—O3—Na2148.88 (12)O2—Na1—O1188.49 (7)
S4—O6—Na1ii149.38 (11)O2—Na1—O11iii79.91 (7)
S4—O8—Na2iv127.9 (1)O6ii—Na1—O981.28 (7)
Na1—O11—Na1iii96.80 (7)O9—Na1—O1076.97 (7)
Na2—O13—Na2v94.18 (7)O9—Na1—O1195.64 (7)
O1—C1—C2124.1 (2)O9—Na1—O11iii113.65 (7)
O1—C1—C6116.6 (2)O10—Na1—O11155.35 (8)
C2—C1—C6119.3 (2)O11—Na1—O11iii83.20 (7)
S2—C2—C1119.80 (18)S3—Na2—O12165.22 (6)
S2—C2—C3119.92 (19)O3—Na2—O12153.71 (8)
C1—C2—C3120.2 (2)O3—Na2—O1387.89 (7)
C2—C3—C4119.4 (2)O3—Na2—O8iv87.03 (7)
S3—C4—C3120.07 (19)O3—Na2—O12153.71 (8)
S3—C4—C5118.89 (19)O3—Na2—O13v102.85 (7)
C3—C4—C5120.9 (2)O8iv—Na2—O1287.12 (7)
C4—C5—C6120.1 (2)O8iv—Na2—O13143.44 (7)
S1—C6—C1122.96 (18)O8iv—Na2—O13v130.56 (7)
S1—C6—C5116.68 (19)O12—Na2—O1381.71 (7)
C1—C6—C5120.1 (2)O12—Na2—O13v100.41 (7)
O5—C7—C8123.5 (2)O13—Na2—O13v85.82 (7)
O5—C7—C12117.0 (2)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y, z; (iv) x+1, y, z+1; (v) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O15iv0.901.952.693 (2)140
O5—H4···O15vi0.821.972.688 (2)146
O9—H7···O4vii0.901.972.831 (3)159
O9—H8···O14vii0.901.862.756 (3)176
O10—H9···O4vii0.902.163.033 (3)166
O10—H9···O90.902.713.055 (3)104
O10—H10···O7iv0.902.062.939 (3)165
O11—H11···O3iii0.902.062.894 (2)153
O11—H12···O12viii0.902.072.858 (3)146
O12—H13···O2ix0.901.912.796 (3)171
O12—H14···O4v0.901.902.793 (3)170
O13—H15···O7x0.902.042.935 (3)173
O13—H16···O9iii0.901.932.787 (3)159
O14—H17···O50.902.042.910 (3)163
Symmetry codes: (iii) x+1, y, z; (iv) x+1, y, z+1; (v) x, y1, z; (vi) x1, y, z; (vii) x+1, y, z; (viii) x, y+1, z; (ix) x, y1, z; (x) x, y1, z1.
 

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