Acta Crystallographica Section E: Structure Reports Online

Acta Crystallogr Sect E Struct Rep Online. 66(Pt 8): m893-m893

(18-Crown-6)(trifluoromethanesulfonato)sodium

Hien Ngoc Phana, Hans-Wolfram Lernera, Michael Boltea*

a. Institut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany

Correspondence e-mail: bolte@chemie.uni-frankfurt.de

© Phan et al. 2010

DOI: 10.1107/S1600536810025961

Published online: 07 July 2010

Abstract

The title compound, [Na(CF₃O₃S)(C₁₂H₂₄O₆)], features a sodium cation that is coordinated by eight O atoms in an irregular hexagonal bipyramidal environment. The equatorial positions are occupied by the six O atoms of an 18-crown-6 ether ring. In the axial positions, there is one O atom of a trifluoromethanesulfonate anion and an ether O atom of a symmetry-equivalent crown ether ring. In this way, centrosymmetric dimers are formed.

Related literature

For the synthesis of hetereoleptic transition metal complexes with silyl ligands, see: Lerner (2005 ▶). For the reaction of Na₂[Fe(CO)₄] with tBu₃SiO₃SCF₃, see: Lerner et al. (2002 ▶). For the structure of similar complexes with trifluoromethanesulfonate, see: Bolte & Lerner (2001 ▶); Lerner & Bolte (2003 ▶); Sofina et al. (2003 ▶); Dinnebier et al. (2004 ▶); Hildebrandt et al. (2006 ▶).

Experimental

Crystal data

[Na(CF₃O₃S)(C₁₂H₂₄O₆)]

M r = 436.37

Monoclinic,

a = 9.4455 (9) Å

b = 15.1723 (12) Å

c = 14.0597 (14) Å

β = 100.828 (8)°

V = 1979.0 (3) Å³

Z = 4

Mo Kα radiation

μ = 0.26 mm⁻¹

T = 173 K

0.33 × 0.20 × 0.19 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.921, T max = 0.943

11867 measured reflections

3697 independent reflections

2856 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.044

wR(F ²) = 0.111

S = 1.03

3697 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å⁻³

Δρmin = −0.44 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2797).

supplementary crystallographic information

Comment

We report here the X-ray crystal structure analysis of sodium trifluorosulfonate as 18-crown-6 ether complex, [Na(18-crown-6)]⁺[CF₃SO₃]⁻. A huge number of hetereoleptic transition metal complexes with silyl ligands are known. Most of these compounds are synthesized by addition of silanes, R₃SiH, to reactive transition metal species (Lerner, 2005). In contrast, few complexes with Fe—Si bonds have been structurally characterized. We have now investigated the reaction of Collman reagent Na₂[Fe(CO)₄] with tBu₃SiO₃SCF₃ (Lerner et al., 2002). When [Na(18-crown-6)]₂[Fe(CO)₄] was treated with two molar equivalents of tBu₃SiO₃SCF₃, the title compound has been formed in nearly quantitative yield, as shown in the scheme below (scheme). The title compound, Na⁺[C₁₂H₂₄O₆].F₃CSO₃⁻, (Fig. 1) features a sodium cation that is coordinated by eight O atoms in an irregular hexagonal bipyramidal environment. The equatorial positions are occupied by the six O atoms of an 18-crown-6 ether ring with Na···O bond distances ranging from 2.5595 (17)Å to 3.0614 (18) Å. In the axial positions there is one O atom of a trifluoromethanesulfonate anion [Na1—O1S 2.3222 (18) Å] and an ether O atom of a symmetry equivalent crown-ether ring [Na1—O10i 2.5792 (17) Å; symmetry operator (i): 1 - x, 1 - y, 1 - z]. In this way, centrosymmetric dimers are formed (Fig. 2).

For the structure of similar complexes with trifluoromethanesulfonate, see: Bolte & Lerner (2001); Lerner & Bolte (2003); Sofina et al. (2003); Dinnebier et al. (2004); Hildebrandt et al. (2006).

Experimental

To a solution of Na₂[Fe(CO)₄] (75 mg, 0.35 mmol) and 18-crown-6 (92 mg, 0.35 mmol) in 20 ml of tetrahydrofuran was added a solution of tBu₃SiO₃SCF₃ (244 mg, 0.70 mmol) in 20 ml toluene at 195 K. The resulting orange-yellow solution was allowed to warm up to room temperature. Colourless crystals of the title compound were grown by storing this solution at room temperature for several days.

Refinement

H atoms were refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C)] using a riding model with C—H = 0.99 Å.

Figures

Fig. 1.View larger versionFig. 1. Perspective view of the title compound with the atom numbering scheme; displacement ellipsoids are at the 50% probability level; H atoms are omitted for clarity.

Fig. 2.View larger versionFig. 2. Partial packing diagram of the title compound showing the formation of a centrosymmetric dimer. Symmetry operator for generating equivalent atoms: 1 - x, 1 - y, 1 - z.

Fig. 3.View larger versionFig. 3. The preparation of the title compound.

Crystal data

See full table

Data collection

See full table

Refinement

See full table

Special details

See full table

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

See full table

Atomic displacement parameters (Å²)

See full table

Geometric parameters (Å, °)

See full table

Symmetry codes: (i) −x+1, −y+1, −z+1.

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References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38.

Bolte, M. & Lerner, H.-W. (2001). Acta Cryst. E57, m231–m232.

Dinnebier, R., Sofina, N. & Jansen, M. (2004). Z. Anorg. Allg. Chem.630, 1613–1616.

Hildebrandt, L., Dinnebier, R. & Jansen, M. (2006). Inorg. Chem.45, 3217–3223.

Lerner, H.-W. (2005). Coord. Chem. Rev.249, 781–798.

Lerner, H.-W. & Bolte, M. (2003). Acta Cryst. E59, m625–m626.

Lerner, H.-W., Wiberg, N., Bolte, M., Nöth, H. & Knizek, J. (2002). Z. Naturforsch. Teil B, 57, 177–182.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Sofina, N., Peters, E. M. & Jansen, M. (2003). Z. Anorg. Allg. Chem.629, 1431–1436.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Stoe & Cie (2001). X-AREA Stoe & Cie, Darmstadt, Germany.

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Fig. 1.

Perspective view of the title compound with the atom numbering scheme; displacement ellipsoids are at the 50% probability level; H atoms are omitted for clarity.

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Fig. 2.

Partial packing diagram of the title compound showing the formation of a centrosymmetric dimer. Symmetry operator for generating equivalent atoms: 1 - x, 1 - y, 1 - z.

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Fig. 3.

The preparation of the title compound.

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[Na(CF₃O₃S)(C₁₂H₂₄O₆)] | F(000) = 912
Mr = 436.37 | Dx = 1.465 Mg m⁻³
Monoclinic, P2₁/n | Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn | Cell parameters from 9688 reflections
a = 9.4455 (9) Å | θ = 3.7–25.3°
b = 15.1723 (12) Å | µ = 0.26 mm⁻¹
c = 14.0597 (14) Å | T = 173 K
β = 100.828 (8)° | Block, colourless
V = 1979.0 (3) Å³ | 0.33 × 0.20 × 0.19 mm
Z = 4 |

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Stoe IPDS II two-circle diffractometer | 3697 independent reflections
Radiation source: fine-focus sealed tube | 2856 reflections with I > 2σ(I)
graphite | Rint = 0.039
ω scans | θmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995) | h = −11→11
Tmin = 0.921, Tmax = 0.943 | k = −18→16
11867 measured reflections | l = −17→17

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Refinement on F² | Secondary atom site location: difference Fourier map
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044 | H-atom parameters constrained
wR(F²) = 0.111 | w = 1/[σ²(Fo²) + (0.056P)² + 0.8425P] where P = (Fo² + 2Fc²)/3
S = 1.03 | (Δ/σ)max < 0.001
3697 reflections | Δρmax = 0.55 e Å⁻³
245 parameters | Δρmin = −0.44 e Å⁻³
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc²λ³/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0078 (11)

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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.

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| x | y | z | Uiso*/Ueq |
S1 | 0.17698 (6) | 0.56948 (4) | 0.77270 (4) | 0.02932 (18) |
O1S | 0.30336 (19) | 0.58449 (15) | 0.73348 (12) | 0.0471 (5) |
O2S | 0.0687 (2) | 0.63629 (17) | 0.75273 (14) | 0.0602 (6) |
O3S | 0.1236 (3) | 0.48077 (17) | 0.76046 (16) | 0.0800 (8) |
C1 | 0.2408 (3) | 0.5785 (2) | 0.90285 (18) | 0.0451 (7) |
F1 | 0.3404 (2) | 0.51872 (14) | 0.93644 (11) | 0.0652 (6) |
F2 | 0.2920 (3) | 0.65607 (15) | 0.92817 (15) | 0.0950 (8) |
F3 | 0.1342 (2) | 0.5651 (2) | 0.95120 (13) | 0.0976 (9) |
Na1 | 0.44188 (9) | 0.58543 (6) | 0.61340 (6) | 0.0272 (2) |
O1 | 0.5534 (2) | 0.75492 (12) | 0.63049 (12) | 0.0429 (5) |
C2 | 0.6072 (3) | 0.7698 (2) | 0.73050 (18) | 0.0479 (7) |
H2A | 0.5265 | 0.7701 | 0.7663 | 0.057* |
H2B | 0.6555 | 0.8279 | 0.7394 | 0.057* |
C3 | 0.7129 (3) | 0.6982 (2) | 0.76966 (19) | 0.0453 (7) |
H3A | 0.7914 | 0.6957 | 0.7319 | 0.054* |
H3B | 0.7560 | 0.7104 | 0.8382 | 0.054* |
O4 | 0.63713 (18) | 0.61655 (12) | 0.76219 (11) | 0.0385 (4) |
C5 | 0.7169 (3) | 0.54774 (19) | 0.81833 (17) | 0.0411 (7) |
H5A | 0.7471 | 0.5669 | 0.8865 | 0.049* |
H5B | 0.8043 | 0.5332 | 0.7921 | 0.049* |
C6 | 0.6208 (3) | 0.46921 (18) | 0.81295 (15) | 0.0356 (6) |
H6A | 0.6708 | 0.4208 | 0.8530 | 0.043* |
H6B | 0.5323 | 0.4843 | 0.8376 | 0.043* |
O7 | 0.58458 (17) | 0.44233 (11) | 0.71374 (10) | 0.0304 (4) |
C8 | 0.4890 (3) | 0.36874 (16) | 0.69957 (16) | 0.0297 (5) |
H8A | 0.3915 | 0.3867 | 0.7082 | 0.036* |
H8B | 0.5242 | 0.3217 | 0.7469 | 0.036* |
C9 | 0.4847 (3) | 0.33610 (15) | 0.59799 (16) | 0.0281 (5) |
H9A | 0.5841 | 0.3240 | 0.5886 | 0.034* |
H9B | 0.4299 | 0.2802 | 0.5885 | 0.034* |
O10 | 0.41817 (16) | 0.39975 (10) | 0.52663 (10) | 0.0247 (3) |
C11 | 0.2659 (2) | 0.38518 (16) | 0.50056 (17) | 0.0299 (5) |
H11A | 0.2241 | 0.3796 | 0.5598 | 0.036* |
H11B | 0.2471 | 0.3297 | 0.4632 | 0.036* |
C12 | 0.1974 (2) | 0.46051 (17) | 0.44098 (15) | 0.0300 (5) |
H12A | 0.2497 | 0.4724 | 0.3876 | 0.036* |
H12B | 0.0962 | 0.4458 | 0.4124 | 0.036* |
O13 | 0.20166 (16) | 0.53687 (11) | 0.50144 (10) | 0.0271 (4) |
C14 | 0.1175 (3) | 0.60634 (18) | 0.45126 (16) | 0.0348 (6) |
H14A | 0.0159 | 0.5872 | 0.4323 | 0.042* |
H14B | 0.1539 | 0.6213 | 0.3917 | 0.042* |
C15 | 0.1263 (3) | 0.68530 (18) | 0.51541 (18) | 0.0378 (6) |
H15A | 0.0633 | 0.7328 | 0.4830 | 0.045* |
H15B | 0.0946 | 0.6700 | 0.5766 | 0.045* |
O16 | 0.27303 (18) | 0.71387 (11) | 0.53489 (11) | 0.0346 (4) |
C17 | 0.2986 (3) | 0.79133 (18) | 0.5926 (2) | 0.0442 (7) |
H17A | 0.2883 | 0.7786 | 0.6600 | 0.053* |
H17B | 0.2289 | 0.8380 | 0.5663 | 0.053* |
C18 | 0.4496 (3) | 0.82041 (17) | 0.5897 (2) | 0.0461 (7) |
H18A | 0.4585 | 0.8318 | 0.5218 | 0.055* |
H18B | 0.4701 | 0.8761 | 0.6263 | 0.055* |

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| U ¹¹ | U ²² | U ³³ | U ¹² | U ¹³ | U ²³
S1 | 0.0269 (3) | 0.0373 (4) | 0.0243 (3) | −0.0015 (3) | 0.0061 (2) | 0.0048 (2)
O1S | 0.0304 (10) | 0.0817 (16) | 0.0323 (9) | 0.0052 (10) | 0.0138 (7) | 0.0117 (9)
O2S | 0.0421 (12) | 0.0902 (18) | 0.0470 (11) | 0.0338 (12) | 0.0053 (9) | 0.0125 (11)
O3S | 0.116 (2) | 0.0615 (16) | 0.0580 (14) | −0.0449 (16) | 0.0047 (13) | 0.0051 (11)
C1 | 0.0474 (16) | 0.0597 (19) | 0.0290 (12) | 0.0230 (15) | 0.0091 (11) | −0.0047 (12)
F1 | 0.0718 (12) | 0.0926 (15) | 0.0305 (8) | 0.0447 (11) | 0.0077 (7) | 0.0110 (8)
F2 | 0.132 (2) | 0.0681 (15) | 0.0672 (13) | 0.0070 (14) | −0.0257 (13) | −0.0318 (11)
F3 | 0.0815 (15) | 0.179 (3) | 0.0427 (10) | 0.0480 (16) | 0.0394 (10) | 0.0185 (12)
Na1 | 0.0237 (5) | 0.0344 (5) | 0.0246 (4) | 0.0006 (4) | 0.0070 (3) | 0.0012 (4)
O1 | 0.0552 (12) | 0.0341 (10) | 0.0403 (10) | −0.0033 (9) | 0.0115 (8) | −0.0154 (8)
C2 | 0.066 (2) | 0.0401 (16) | 0.0391 (14) | −0.0176 (15) | 0.0135 (13) | −0.0194 (12)
C3 | 0.0407 (16) | 0.0529 (18) | 0.0414 (14) | −0.0238 (14) | 0.0050 (11) | −0.0228 (13)
O4 | 0.0343 (10) | 0.0438 (11) | 0.0334 (9) | −0.0105 (8) | −0.0041 (7) | −0.0058 (8)
C5 | 0.0356 (14) | 0.0611 (19) | 0.0228 (11) | 0.0009 (13) | −0.0047 (10) | −0.0059 (11)
C6 | 0.0392 (14) | 0.0506 (16) | 0.0162 (10) | 0.0062 (12) | 0.0031 (9) | 0.0020 (10)
O7 | 0.0337 (9) | 0.0384 (10) | 0.0194 (7) | −0.0051 (7) | 0.0055 (6) | 0.0012 (6)
C8 | 0.0322 (13) | 0.0283 (13) | 0.0310 (12) | 0.0021 (10) | 0.0121 (9) | 0.0083 (9)
C9 | 0.0294 (12) | 0.0218 (12) | 0.0345 (12) | 0.0034 (10) | 0.0101 (9) | 0.0014 (9)
O10 | 0.0210 (8) | 0.0252 (8) | 0.0288 (8) | −0.0018 (6) | 0.0067 (6) | 0.0010 (6)
C11 | 0.0222 (12) | 0.0322 (13) | 0.0353 (12) | −0.0101 (10) | 0.0052 (9) | −0.0049 (10)
C12 | 0.0232 (12) | 0.0432 (15) | 0.0222 (10) | −0.0071 (11) | 0.0005 (8) | −0.0050 (9)
O13 | 0.0233 (8) | 0.0359 (9) | 0.0206 (7) | 0.0048 (7) | 0.0002 (6) | 0.0046 (6)
C14 | 0.0225 (12) | 0.0502 (16) | 0.0304 (12) | 0.0101 (11) | 0.0020 (9) | 0.0152 (11)
C15 | 0.0275 (13) | 0.0443 (16) | 0.0441 (14) | 0.0162 (12) | 0.0130 (10) | 0.0163 (12)
O16 | 0.0358 (10) | 0.0300 (10) | 0.0425 (9) | 0.0062 (8) | 0.0185 (7) | 0.0015 (7)
C17 | 0.0585 (19) | 0.0302 (15) | 0.0487 (15) | 0.0136 (13) | 0.0225 (13) | 0.0000 (11)
C18 | 0.067 (2) | 0.0215 (13) | 0.0533 (16) | −0.0007 (13) | 0.0213 (14) | −0.0059 (11)

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S1—O1S | 1.4241 (18) | O7—C8 | 1.426 (3)
S1—O2S | 1.430 (2) | C8—C9 | 1.505 (3)
S1—O3S | 1.436 (2) | C8—H8A | 0.9900
S1—C1 | 1.821 (3) | C8—H8B | 0.9900
O1S—Na1 | 2.3222 (18) | C9—O10 | 1.448 (3)
C1—F2 | 1.296 (4) | C9—H9A | 0.9900
C1—F1 | 1.328 (3) | C9—H9B | 0.9900
C1—F3 | 1.333 (4) | O10—C11 | 1.433 (3)
Na1—O4 | 2.5595 (17) | O10—Na1i | 2.5792 (17)
Na1—O10i | 2.5792 (17) | C11—C12 | 1.491 (3)
Na1—O13 | 2.6129 (17) | C11—H11A | 0.9900
Na1—O16 | 2.6265 (19) | C11—H11B | 0.9900
Na1—O1 | 2.772 (2) | C12—O13 | 1.433 (3)
Na1—O7 | 2.7939 (19) | C12—H12A | 0.9900
O1—C2 | 1.421 (3) | C12—H12B | 0.9900
O1—C18 | 1.437 (3) | O13—C14 | 1.425 (3)
C2—C3 | 1.508 (4) | C14—C15 | 1.493 (4)
C2—H2A | 0.9900 | C14—H14A | 0.9900
C2—H2B | 0.9900 | C14—H14B | 0.9900
C3—O4 | 1.425 (3) | C15—O16 | 1.429 (3)
C3—H3A | 0.9900 | C15—H15A | 0.9900
C3—H3B | 0.9900 | C15—H15B | 0.9900
O4—C5 | 1.434 (3) | O16—C17 | 1.423 (3)
C5—C6 | 1.491 (4) | C17—C18 | 1.501 (4)
C5—H5A | 0.9900 | C17—H17A | 0.9900
C5—H5B | 0.9900 | C17—H17B | 0.9900
C6—O7 | 1.432 (3) | C18—H18A | 0.9900
C6—H6A | 0.9900 | C18—H18B | 0.9900
C6—H6B | 0.9900 |  |
O1S—S1—O2S | 115.53 (13) | C5—C6—H6B | 110.1
O1S—S1—O3S | 113.85 (16) | H6A—C6—H6B | 108.4
O2S—S1—O3S | 114.78 (17) | C8—O7—C6 | 112.85 (17)
O1S—S1—C1 | 103.51 (12) | C8—O7—Na1 | 107.78 (12)
O2S—S1—C1 | 103.52 (12) | C6—O7—Na1 | 105.96 (14)
O3S—S1—C1 | 103.50 (14) | O7—C8—C9 | 107.10 (17)
S1—O1S—Na1 | 155.54 (12) | O7—C8—H8A | 110.3
F2—C1—F1 | 108.7 (3) | C9—C8—H8A | 110.3
F2—C1—F3 | 106.1 (3) | O7—C8—H8B | 110.3
F1—C1—F3 | 105.5 (2) | C9—C8—H8B | 110.3
F2—C1—S1 | 112.3 (2) | H8A—C8—H8B | 108.5
F1—C1—S1 | 112.63 (18) | O10—C9—C8 | 111.66 (18)
F3—C1—S1 | 111.2 (2) | O10—C9—H9A | 109.3
O1S—Na1—O4 | 79.91 (6) | C8—C9—H9A | 109.3
O1S—Na1—O10i | 174.33 (7) | O10—C9—H9B | 109.3
O4—Na1—O10i | 102.35 (6) | C8—C9—H9B | 109.3
O1S—Na1—O13 | 83.81 (6) | H9A—C9—H9B | 108.0
O4—Na1—O13 | 162.80 (6) | C11—O10—C9 | 110.99 (17)
O10i—Na1—O13 | 94.38 (5) | C11—O10—Na1i | 116.86 (12)
O1S—Na1—O16 | 85.96 (7) | C9—O10—Na1i | 111.66 (12)
O4—Na1—O16 | 119.60 (7) | O10—C11—C12 | 109.53 (18)
O10i—Na1—O16 | 88.42 (5) | O10—C11—H11A | 109.8
O13—Na1—O16 | 64.28 (6) | C12—C11—H11A | 109.8
O1S—Na1—O1 | 101.51 (7) | O10—C11—H11B | 109.8
O4—Na1—O1 | 63.53 (6) | C12—C11—H11B | 109.8
O10i—Na1—O1 | 75.19 (5) | H11A—C11—H11B | 108.2
O13—Na1—O1 | 125.92 (6) | O13—C12—C11 | 109.00 (17)
O16—Na1—O1 | 62.54 (6) | O13—C12—H12A | 109.9
O1S—Na1—O7 | 84.97 (6) | C11—C12—H12A | 109.9
O4—Na1—O7 | 61.67 (6) | O13—C12—H12B | 109.9
O10i—Na1—O7 | 100.68 (5) | C11—C12—H12B | 109.9
O13—Na1—O7 | 111.53 (6) | H12A—C12—H12B | 108.3
O16—Na1—O7 | 170.41 (6) | C14—O13—C12 | 110.70 (17)
O1—Na1—O7 | 122.53 (6) | C14—O13—Na1 | 115.48 (14)
C2—O1—C18 | 112.0 (2) | C12—O13—Na1 | 120.65 (13)
C2—O1—Na1 | 107.03 (15) | O13—C14—C15 | 109.39 (18)
C18—O1—Na1 | 112.78 (15) | O13—C14—H14A | 109.8
O1—C2—C3 | 109.6 (2) | C15—C14—H14A | 109.8
O1—C2—H2A | 109.7 | O13—C14—H14B | 109.8
C3—C2—H2A | 109.7 | C15—C14—H14B | 109.8
O1—C2—H2B | 109.7 | H14A—C14—H14B | 108.2
C3—C2—H2B | 109.7 | O16—C15—C14 | 107.54 (19)
H2A—C2—H2B | 108.2 | O16—C15—H15A | 110.2
O4—C3—C2 | 108.1 (2) | C14—C15—H15A | 110.2
O4—C3—H3A | 110.1 | O16—C15—H15B | 110.2
C2—C3—H3A | 110.1 | C14—C15—H15B | 110.2
O4—C3—H3B | 110.1 | H15A—C15—H15B | 108.5
C2—C3—H3B | 110.1 | C17—O16—C15 | 114.5 (2)
H3A—C3—H3B | 108.4 | C17—O16—Na1 | 110.39 (15)
C3—O4—C5 | 112.80 (19) | C15—O16—Na1 | 110.24 (14)
C3—O4—Na1 | 119.71 (15) | O16—C17—C18 | 106.7 (2)
C5—O4—Na1 | 122.61 (14) | O16—C17—H17A | 110.4
O4—C5—C6 | 107.58 (19) | C18—C17—H17A | 110.4
O4—C5—H5A | 110.2 | O16—C17—H17B | 110.4
C6—C5—H5A | 110.2 | C18—C17—H17B | 110.4
O4—C5—H5B | 110.2 | H17A—C17—H17B | 108.6
C6—C5—H5B | 110.2 | O1—C18—C17 | 111.5 (2)
H5A—C5—H5B | 108.5 | O1—C18—H18A | 109.3
O7—C6—C5 | 108.00 (18) | C17—C18—H18A | 109.3
O7—C6—H6A | 110.1 | O1—C18—H18B | 109.3
C5—C6—H6A | 110.1 | C17—C18—H18B | 109.3
O7—C6—H6B | 110.1 | H18A—C18—H18B | 108.0
O2S—S1—O1S—Na1 | −80.8 (4) | O1S—Na1—O7—C8 | 71.26 (13)
O3S—S1—O1S—Na1 | 55.2 (4) | O4—Na1—O7—C8 | 152.50 (14)
C1—S1—O1S—Na1 | 166.8 (3) | O10i—Na1—O7—C8 | −109.13 (12)
O1S—S1—C1—F2 | 61.9 (2) | O13—Na1—O7—C8 | −10.05 (13)
O2S—S1—C1—F2 | −59.0 (3) | O1—Na1—O7—C8 | 171.72 (12)
O3S—S1—C1—F2 | −179.1 (2) | O1S—Na1—O7—C6 | −49.80 (14)
O1S—S1—C1—F1 | −61.2 (3) | O4—Na1—O7—C6 | 31.44 (13)
O2S—S1—C1—F1 | 177.9 (2) | O10i—Na1—O7—C6 | 129.81 (14)
O3S—S1—C1—F1 | 57.8 (3) | O13—Na1—O7—C6 | −131.11 (14)
O1S—S1—C1—F3 | −179.4 (2) | O1—Na1—O7—C6 | 50.66 (15)
O2S—S1—C1—F3 | 59.7 (3) | C6—O7—C8—C9 | −168.50 (19)
O3S—S1—C1—F3 | −60.4 (3) | Na1—O7—C8—C9 | 74.85 (18)
S1—O1S—Na1—O4 | −169.0 (3) | O7—C8—C9—O10 | −66.6 (2)
S1—O1S—Na1—O13 | 5.4 (3) | C8—C9—O10—C11 | −90.6 (2)
S1—O1S—Na1—O16 | 70.0 (3) | C8—C9—O10—Na1i | 137.13 (15)
S1—O1S—Na1—O1 | 130.9 (3) | C9—O10—C11—C12 | 170.05 (18)
S1—O1S—Na1—O7 | −106.9 (3) | Na1i—O10—C11—C12 | −60.3 (2)
O1S—Na1—O1—C2 | 47.64 (17) | O10—C11—C12—O13 | −70.3 (2)
O4—Na1—O1—C2 | −24.84 (16) | C11—C12—O13—C14 | −170.82 (18)
O10i—Na1—O1—C2 | −137.10 (17) | C11—C12—O13—Na1 | 49.8 (2)
O13—Na1—O1—C2 | 138.30 (16) | O1S—Na1—O13—C14 | 94.66 (15)
O16—Na1—O1—C2 | 126.87 (17) | O4—Na1—O13—C14 | 113.5 (2)
O7—Na1—O1—C2 | −43.73 (18) | O10i—Na1—O13—C14 | −79.95 (14)
O1S—Na1—O1—C18 | −76.03 (16) | O16—Na1—O13—C14 | 6.18 (13)
O4—Na1—O1—C18 | −148.50 (17) | O1—Na1—O13—C14 | −5.08 (16)
O10i—Na1—O1—C18 | 99.24 (16) | O7—Na1—O13—C14 | 176.75 (13)
O13—Na1—O1—C18 | 14.64 (18) | O1S—Na1—O13—C12 | −127.82 (15)
O16—Na1—O1—C18 | 3.21 (15) | O4—Na1—O13—C12 | −108.9 (2)
O7—Na1—O1—C18 | −167.39 (15) | O10i—Na1—O13—C12 | 57.58 (15)
C18—O1—C2—C3 | 178.8 (2) | O16—Na1—O13—C12 | 143.70 (16)
Na1—O1—C2—C3 | 54.7 (2) | O1—Na1—O13—C12 | 132.44 (14)
O1—C2—C3—O4 | −63.7 (3) | O7—Na1—O13—C12 | −45.72 (16)
C2—C3—O4—C5 | −165.5 (2) | C12—O13—C14—C15 | −178.97 (19)
C2—C3—O4—Na1 | 38.6 (3) | Na1—O13—C14—C15 | −37.4 (2)
O1S—Na1—O4—C3 | −116.58 (19) | O13—C14—C15—O16 | 63.5 (2)
O10i—Na1—O4—C3 | 58.12 (18) | C14—C15—O16—C17 | 177.68 (19)
O13—Na1—O4—C3 | −135.6 (2) | C14—C15—O16—Na1 | −57.14 (19)
O16—Na1—O4—C3 | −37.1 (2) | O1S—Na1—O16—C17 | 69.56 (16)
O1—Na1—O4—C3 | −8.22 (17) | O4—Na1—O16—C17 | −6.43 (17)
O7—Na1—O4—C3 | 153.72 (19) | O10i—Na1—O16—C17 | −109.75 (15)
O1S—Na1—O4—C5 | 89.95 (18) | O13—Na1—O16—C17 | 154.63 (16)
O10i—Na1—O4—C5 | −95.35 (18) | O1S—Na1—O16—C15 | −57.94 (15)
O13—Na1—O4—C5 | 70.9 (3) | O4—Na1—O16—C15 | −133.92 (14)
O16—Na1—O4—C5 | 169.38 (16) | O10i—Na1—O16—C15 | 122.76 (14)
O1—Na1—O4—C5 | −161.69 (19) | O13—Na1—O16—C15 | 27.13 (14)
O7—Na1—O4—C5 | 0.25 (16) | O1—Na1—O16—C15 | −163.13 (15)
C3—O4—C5—C6 | 174.10 (19) | C15—O16—C17—C18 | −169.6 (2)
Na1—O4—C5—C6 | −30.8 (3) | Na1—O16—C17—C18 | 65.3 (2)
O4—C5—C6—O7 | 61.9 (3) | C2—O1—C18—C17 | −93.2 (3)
C5—C6—O7—C8 | −178.3 (2) | Na1—O1—C18—C17 | 27.7 (2)
C5—C6—O7—Na1 | −60.6 (2) | O16—C17—C18—O1 | −62.0 (3)

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