(18-Crown-6)(trifluoro­methane­sulfonato)­sodium

Phan, H.N.; Lerner, H.-W.; Bolte, M.

doi:10.1107/S1600536810025961

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m893

https://doi.org/10.1107/S1600536810025961

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(18-Crown-6)(trifluoromethanesulfonato)sodium

Hien Ngoc Phan,^a Hans-Wolfram Lerner ^a and Michael Bolte ^a ^*

^aInstitut 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

(Received 30 June 2010; accepted 1 July 2010; online 7 July 2010)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.111
S = 1.03
3697 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810025961/ng2797sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025961/ng2797Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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). Ffor 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 top

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.

Structure description top

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). Ffor 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).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).

Figures top

	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.
	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.
	Fig. 3. The preparation of the title compound.

(1,4,7,10,13,16-hexaoxacyclooctadecane)(trifluoromethanesulfonato)sodium top

Crystal data top

[Na(CF₃O₃S)(C₁₂H₂₄O₆)]	F(000) = 912
M_r = 436.37	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.056P)² + 0.8425P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3697 reflections	Δρ_max = 0.55 e Å⁻³
245 parameters	Δρ_min = −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)

Crystal data top

[Na(CF₃O₃S)(C₁₂H₂₄O₆)]	V = 1979.0 (3) Å³
M_r = 436.37	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.4455 (9) Å	µ = 0.26 mm⁻¹
b = 15.1723 (12) Å	T = 173 K
c = 14.0597 (14) Å	0.33 × 0.20 × 0.19 mm
β = 100.828 (8)°

Data collection top

Stoe IPDS II two-circle diffractometer	3697 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	2856 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.943	R_int = 0.039
11867 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	Δρ_max = 0.55 e Å⁻³
3697 reflections	Δρ_min = −0.44 e Å⁻³
245 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Na(CF₃O₃S)(C₁₂H₂₄O₆)]
M_r	436.37
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.4455 (9), 15.1723 (12), 14.0597 (14)
β (°)	100.828 (8)
V (Å³)	1979.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.33 × 0.20 × 0.19

Data collection
Diffractometer	Stoe IPDS II two-circle
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.921, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	11867, 3697, 2856
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.111, 1.03
No. of reflections	3697
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.44

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Lerner, H.-W., Wiberg, N., Bolte, M., Nöth, H. & Knizek, J. (2002). Z. Naturforsch. Teil B, 57, 177–182. CAS Google Scholar
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Sofina, N., Peters, E. M. & Jansen, M. (2003). Z. Anorg. Allg. Chem. 629, 1431–1436. Web of Science CSD CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar