Literature DB >> 21588137

(18-Crown-6)(trifluoro-methane-sulfonato)-sodium.

Hien Ngoc Phan1, Hans-Wolfram Lerner, Michael Bolte.   

Abstract

The title compound, [Na(CF(3)O(3)S)(C(12)H(24)O(6))], features a sodium cation that is coordinated by eight O atoms in an irregular hexa-gonal 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 trifluoro-methane-sulfonate anion and an ether O atom of a symmetry-equivalent crown ether ring. In this way, centrosymmetric dimers are formed.

Entities:  

Year:  2010        PMID: 21588137      PMCID: PMC3007570          DOI: 10.1107/S1600536810025961

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


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 = 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. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025961/ng2797sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025961/ng2797Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Na(CF3O3S)(C12H24O6)]F(000) = 912
Mr = 436.37Dx = 1.465 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9688 reflections
a = 9.4455 (9) Åθ = 3.7–25.3°
b = 15.1723 (12) ŵ = 0.26 mm1
c = 14.0597 (14) ÅT = 173 K
β = 100.828 (8)°Block, colourless
V = 1979.0 (3) Å30.33 × 0.20 × 0.19 mm
Z = 4
Stoe IPDS II two-circle diffractometer3697 independent reflections
Radiation source: fine-focus sealed tube2856 reflections with I > 2σ(I)
graphiteRint = 0.039
ω scansθmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)h = −11→11
Tmin = 0.921, Tmax = 0.943k = −18→16
11867 measured reflectionsl = −17→17
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.111w = 1/[σ2(Fo2) + (0.056P)2 + 0.8425P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3697 reflectionsΔρmax = 0.55 e Å3
245 parametersΔρmin = −0.44 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0078 (11)
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.
xyzUiso*/Ueq
S10.17698 (6)0.56948 (4)0.77270 (4)0.02932 (18)
O1S0.30336 (19)0.58449 (15)0.73348 (12)0.0471 (5)
O2S0.0687 (2)0.63629 (17)0.75273 (14)0.0602 (6)
O3S0.1236 (3)0.48077 (17)0.76046 (16)0.0800 (8)
C10.2408 (3)0.5785 (2)0.90285 (18)0.0451 (7)
F10.3404 (2)0.51872 (14)0.93644 (11)0.0652 (6)
F20.2920 (3)0.65607 (15)0.92817 (15)0.0950 (8)
F30.1342 (2)0.5651 (2)0.95120 (13)0.0976 (9)
Na10.44188 (9)0.58543 (6)0.61340 (6)0.0272 (2)
O10.5534 (2)0.75492 (12)0.63049 (12)0.0429 (5)
C20.6072 (3)0.7698 (2)0.73050 (18)0.0479 (7)
H2A0.52650.77010.76630.057*
H2B0.65550.82790.73940.057*
C30.7129 (3)0.6982 (2)0.76966 (19)0.0453 (7)
H3A0.79140.69570.73190.054*
H3B0.75600.71040.83820.054*
O40.63713 (18)0.61655 (12)0.76219 (11)0.0385 (4)
C50.7169 (3)0.54774 (19)0.81833 (17)0.0411 (7)
H5A0.74710.56690.88650.049*
H5B0.80430.53320.79210.049*
C60.6208 (3)0.46921 (18)0.81295 (15)0.0356 (6)
H6A0.67080.42080.85300.043*
H6B0.53230.48430.83760.043*
O70.58458 (17)0.44233 (11)0.71374 (10)0.0304 (4)
C80.4890 (3)0.36874 (16)0.69957 (16)0.0297 (5)
H8A0.39150.38670.70820.036*
H8B0.52420.32170.74690.036*
C90.4847 (3)0.33610 (15)0.59799 (16)0.0281 (5)
H9A0.58410.32400.58860.034*
H9B0.42990.28020.58850.034*
O100.41817 (16)0.39975 (10)0.52663 (10)0.0247 (3)
C110.2659 (2)0.38518 (16)0.50056 (17)0.0299 (5)
H11A0.22410.37960.55980.036*
H11B0.24710.32970.46320.036*
C120.1974 (2)0.46051 (17)0.44098 (15)0.0300 (5)
H12A0.24970.47240.38760.036*
H12B0.09620.44580.41240.036*
O130.20166 (16)0.53687 (11)0.50144 (10)0.0271 (4)
C140.1175 (3)0.60634 (18)0.45126 (16)0.0348 (6)
H14A0.01590.58720.43230.042*
H14B0.15390.62130.39170.042*
C150.1263 (3)0.68530 (18)0.51541 (18)0.0378 (6)
H15A0.06330.73280.48300.045*
H15B0.09460.67000.57660.045*
O160.27303 (18)0.71387 (11)0.53489 (11)0.0346 (4)
C170.2986 (3)0.79133 (18)0.5926 (2)0.0442 (7)
H17A0.28830.77860.66000.053*
H17B0.22890.83800.56630.053*
C180.4496 (3)0.82041 (17)0.5897 (2)0.0461 (7)
H18A0.45850.83180.52180.055*
H18B0.47010.87610.62630.055*
U11U22U33U12U13U23
S10.0269 (3)0.0373 (4)0.0243 (3)−0.0015 (3)0.0061 (2)0.0048 (2)
O1S0.0304 (10)0.0817 (16)0.0323 (9)0.0052 (10)0.0138 (7)0.0117 (9)
O2S0.0421 (12)0.0902 (18)0.0470 (11)0.0338 (12)0.0053 (9)0.0125 (11)
O3S0.116 (2)0.0615 (16)0.0580 (14)−0.0449 (16)0.0047 (13)0.0051 (11)
C10.0474 (16)0.0597 (19)0.0290 (12)0.0230 (15)0.0091 (11)−0.0047 (12)
F10.0718 (12)0.0926 (15)0.0305 (8)0.0447 (11)0.0077 (7)0.0110 (8)
F20.132 (2)0.0681 (15)0.0672 (13)0.0070 (14)−0.0257 (13)−0.0318 (11)
F30.0815 (15)0.179 (3)0.0427 (10)0.0480 (16)0.0394 (10)0.0185 (12)
Na10.0237 (5)0.0344 (5)0.0246 (4)0.0006 (4)0.0070 (3)0.0012 (4)
O10.0552 (12)0.0341 (10)0.0403 (10)−0.0033 (9)0.0115 (8)−0.0154 (8)
C20.066 (2)0.0401 (16)0.0391 (14)−0.0176 (15)0.0135 (13)−0.0194 (12)
C30.0407 (16)0.0529 (18)0.0414 (14)−0.0238 (14)0.0050 (11)−0.0228 (13)
O40.0343 (10)0.0438 (11)0.0334 (9)−0.0105 (8)−0.0041 (7)−0.0058 (8)
C50.0356 (14)0.0611 (19)0.0228 (11)0.0009 (13)−0.0047 (10)−0.0059 (11)
C60.0392 (14)0.0506 (16)0.0162 (10)0.0062 (12)0.0031 (9)0.0020 (10)
O70.0337 (9)0.0384 (10)0.0194 (7)−0.0051 (7)0.0055 (6)0.0012 (6)
C80.0322 (13)0.0283 (13)0.0310 (12)0.0021 (10)0.0121 (9)0.0083 (9)
C90.0294 (12)0.0218 (12)0.0345 (12)0.0034 (10)0.0101 (9)0.0014 (9)
O100.0210 (8)0.0252 (8)0.0288 (8)−0.0018 (6)0.0067 (6)0.0010 (6)
C110.0222 (12)0.0322 (13)0.0353 (12)−0.0101 (10)0.0052 (9)−0.0049 (10)
C120.0232 (12)0.0432 (15)0.0222 (10)−0.0071 (11)0.0005 (8)−0.0050 (9)
O130.0233 (8)0.0359 (9)0.0206 (7)0.0048 (7)0.0002 (6)0.0046 (6)
C140.0225 (12)0.0502 (16)0.0304 (12)0.0101 (11)0.0020 (9)0.0152 (11)
C150.0275 (13)0.0443 (16)0.0441 (14)0.0162 (12)0.0130 (10)0.0163 (12)
O160.0358 (10)0.0300 (10)0.0425 (9)0.0062 (8)0.0185 (7)0.0015 (7)
C170.0585 (19)0.0302 (15)0.0487 (15)0.0136 (13)0.0225 (13)0.0000 (11)
C180.067 (2)0.0215 (13)0.0533 (16)−0.0007 (13)0.0213 (14)−0.0059 (11)
S1—O1S1.4241 (18)O7—C81.426 (3)
S1—O2S1.430 (2)C8—C91.505 (3)
S1—O3S1.436 (2)C8—H8A0.9900
S1—C11.821 (3)C8—H8B0.9900
O1S—Na12.3222 (18)C9—O101.448 (3)
C1—F21.296 (4)C9—H9A0.9900
C1—F11.328 (3)C9—H9B0.9900
C1—F31.333 (4)O10—C111.433 (3)
Na1—O42.5595 (17)O10—Na1i2.5792 (17)
Na1—O10i2.5792 (17)C11—C121.491 (3)
Na1—O132.6129 (17)C11—H11A0.9900
Na1—O162.6265 (19)C11—H11B0.9900
Na1—O12.772 (2)C12—O131.433 (3)
Na1—O72.7939 (19)C12—H12A0.9900
O1—C21.421 (3)C12—H12B0.9900
O1—C181.437 (3)O13—C141.425 (3)
C2—C31.508 (4)C14—C151.493 (4)
C2—H2A0.9900C14—H14A0.9900
C2—H2B0.9900C14—H14B0.9900
C3—O41.425 (3)C15—O161.429 (3)
C3—H3A0.9900C15—H15A0.9900
C3—H3B0.9900C15—H15B0.9900
O4—C51.434 (3)O16—C171.423 (3)
C5—C61.491 (4)C17—C181.501 (4)
C5—H5A0.9900C17—H17A0.9900
C5—H5B0.9900C17—H17B0.9900
C6—O71.432 (3)C18—H18A0.9900
C6—H6A0.9900C18—H18B0.9900
C6—H6B0.9900
O1S—S1—O2S115.53 (13)C5—C6—H6B110.1
O1S—S1—O3S113.85 (16)H6A—C6—H6B108.4
O2S—S1—O3S114.78 (17)C8—O7—C6112.85 (17)
O1S—S1—C1103.51 (12)C8—O7—Na1107.78 (12)
O2S—S1—C1103.52 (12)C6—O7—Na1105.96 (14)
O3S—S1—C1103.50 (14)O7—C8—C9107.10 (17)
S1—O1S—Na1155.54 (12)O7—C8—H8A110.3
F2—C1—F1108.7 (3)C9—C8—H8A110.3
F2—C1—F3106.1 (3)O7—C8—H8B110.3
F1—C1—F3105.5 (2)C9—C8—H8B110.3
F2—C1—S1112.3 (2)H8A—C8—H8B108.5
F1—C1—S1112.63 (18)O10—C9—C8111.66 (18)
F3—C1—S1111.2 (2)O10—C9—H9A109.3
O1S—Na1—O479.91 (6)C8—C9—H9A109.3
O1S—Na1—O10i174.33 (7)O10—C9—H9B109.3
O4—Na1—O10i102.35 (6)C8—C9—H9B109.3
O1S—Na1—O1383.81 (6)H9A—C9—H9B108.0
O4—Na1—O13162.80 (6)C11—O10—C9110.99 (17)
O10i—Na1—O1394.38 (5)C11—O10—Na1i116.86 (12)
O1S—Na1—O1685.96 (7)C9—O10—Na1i111.66 (12)
O4—Na1—O16119.60 (7)O10—C11—C12109.53 (18)
O10i—Na1—O1688.42 (5)O10—C11—H11A109.8
O13—Na1—O1664.28 (6)C12—C11—H11A109.8
O1S—Na1—O1101.51 (7)O10—C11—H11B109.8
O4—Na1—O163.53 (6)C12—C11—H11B109.8
O10i—Na1—O175.19 (5)H11A—C11—H11B108.2
O13—Na1—O1125.92 (6)O13—C12—C11109.00 (17)
O16—Na1—O162.54 (6)O13—C12—H12A109.9
O1S—Na1—O784.97 (6)C11—C12—H12A109.9
O4—Na1—O761.67 (6)O13—C12—H12B109.9
O10i—Na1—O7100.68 (5)C11—C12—H12B109.9
O13—Na1—O7111.53 (6)H12A—C12—H12B108.3
O16—Na1—O7170.41 (6)C14—O13—C12110.70 (17)
O1—Na1—O7122.53 (6)C14—O13—Na1115.48 (14)
C2—O1—C18112.0 (2)C12—O13—Na1120.65 (13)
C2—O1—Na1107.03 (15)O13—C14—C15109.39 (18)
C18—O1—Na1112.78 (15)O13—C14—H14A109.8
O1—C2—C3109.6 (2)C15—C14—H14A109.8
O1—C2—H2A109.7O13—C14—H14B109.8
C3—C2—H2A109.7C15—C14—H14B109.8
O1—C2—H2B109.7H14A—C14—H14B108.2
C3—C2—H2B109.7O16—C15—C14107.54 (19)
H2A—C2—H2B108.2O16—C15—H15A110.2
O4—C3—C2108.1 (2)C14—C15—H15A110.2
O4—C3—H3A110.1O16—C15—H15B110.2
C2—C3—H3A110.1C14—C15—H15B110.2
O4—C3—H3B110.1H15A—C15—H15B108.5
C2—C3—H3B110.1C17—O16—C15114.5 (2)
H3A—C3—H3B108.4C17—O16—Na1110.39 (15)
C3—O4—C5112.80 (19)C15—O16—Na1110.24 (14)
C3—O4—Na1119.71 (15)O16—C17—C18106.7 (2)
C5—O4—Na1122.61 (14)O16—C17—H17A110.4
O4—C5—C6107.58 (19)C18—C17—H17A110.4
O4—C5—H5A110.2O16—C17—H17B110.4
C6—C5—H5A110.2C18—C17—H17B110.4
O4—C5—H5B110.2H17A—C17—H17B108.6
C6—C5—H5B110.2O1—C18—C17111.5 (2)
H5A—C5—H5B108.5O1—C18—H18A109.3
O7—C6—C5108.00 (18)C17—C18—H18A109.3
O7—C6—H6A110.1O1—C18—H18B109.3
C5—C6—H6A110.1C17—C18—H18B109.3
O7—C6—H6B110.1H18A—C18—H18B108.0
O2S—S1—O1S—Na1−80.8 (4)O1S—Na1—O7—C871.26 (13)
O3S—S1—O1S—Na155.2 (4)O4—Na1—O7—C8152.50 (14)
C1—S1—O1S—Na1166.8 (3)O10i—Na1—O7—C8−109.13 (12)
O1S—S1—C1—F261.9 (2)O13—Na1—O7—C8−10.05 (13)
O2S—S1—C1—F2−59.0 (3)O1—Na1—O7—C8171.72 (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—C631.44 (13)
O2S—S1—C1—F1177.9 (2)O10i—Na1—O7—C6129.81 (14)
O3S—S1—C1—F157.8 (3)O13—Na1—O7—C6−131.11 (14)
O1S—S1—C1—F3−179.4 (2)O1—Na1—O7—C650.66 (15)
O2S—S1—C1—F359.7 (3)C6—O7—C8—C9−168.50 (19)
O3S—S1—C1—F3−60.4 (3)Na1—O7—C8—C974.85 (18)
S1—O1S—Na1—O4−169.0 (3)O7—C8—C9—O10−66.6 (2)
S1—O1S—Na1—O135.4 (3)C8—C9—O10—C11−90.6 (2)
S1—O1S—Na1—O1670.0 (3)C8—C9—O10—Na1i137.13 (15)
S1—O1S—Na1—O1130.9 (3)C9—O10—C11—C12170.05 (18)
S1—O1S—Na1—O7−106.9 (3)Na1i—O10—C11—C12−60.3 (2)
O1S—Na1—O1—C247.64 (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—Na149.8 (2)
O13—Na1—O1—C2138.30 (16)O1S—Na1—O13—C1494.66 (15)
O16—Na1—O1—C2126.87 (17)O4—Na1—O13—C14113.5 (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—C146.18 (13)
O4—Na1—O1—C18−148.50 (17)O1—Na1—O13—C14−5.08 (16)
O10i—Na1—O1—C1899.24 (16)O7—Na1—O13—C14176.75 (13)
O13—Na1—O1—C1814.64 (18)O1S—Na1—O13—C12−127.82 (15)
O16—Na1—O1—C183.21 (15)O4—Na1—O13—C12−108.9 (2)
O7—Na1—O1—C18−167.39 (15)O10i—Na1—O13—C1257.58 (15)
C18—O1—C2—C3178.8 (2)O16—Na1—O13—C12143.70 (16)
Na1—O1—C2—C354.7 (2)O1—Na1—O13—C12132.44 (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—Na138.6 (3)Na1—O13—C14—C15−37.4 (2)
O1S—Na1—O4—C3−116.58 (19)O13—C14—C15—O1663.5 (2)
O10i—Na1—O4—C358.12 (18)C14—C15—O16—C17177.68 (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—C1769.56 (16)
O1—Na1—O4—C3−8.22 (17)O4—Na1—O16—C17−6.43 (17)
O7—Na1—O4—C3153.72 (19)O10i—Na1—O16—C17−109.75 (15)
O1S—Na1—O4—C589.95 (18)O13—Na1—O16—C17154.63 (16)
O10i—Na1—O4—C5−95.35 (18)O1S—Na1—O16—C15−57.94 (15)
O13—Na1—O4—C570.9 (3)O4—Na1—O16—C15−133.92 (14)
O16—Na1—O4—C5169.38 (16)O10i—Na1—O16—C15122.76 (14)
O1—Na1—O4—C5−161.69 (19)O13—Na1—O16—C1527.13 (14)
O7—Na1—O4—C50.25 (16)O1—Na1—O16—C15−163.13 (15)
C3—O4—C5—C6174.10 (19)C15—O16—C17—C18−169.6 (2)
Na1—O4—C5—C6−30.8 (3)Na1—O16—C17—C1865.3 (2)
O4—C5—C6—O761.9 (3)C2—O1—C18—C17−93.2 (3)
C5—C6—O7—C8−178.3 (2)Na1—O1—C18—C1727.7 (2)
C5—C6—O7—Na1−60.6 (2)O16—C17—C18—O1−62.0 (3)
  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  An empirical correction for absorption anisotropy.

Authors:  R H Blessing
Journal:  Acta Crystallogr A       Date:  1995-01-01       Impact factor: 2.290

3.  Crystal structure and ionic conductivity of three polymorphic phases of rubidium trifluoromethyl sulfonate, RbSO3CF3.

Authors:  Lars Hildebrandt; Robert Dinnebier; Martin Jansen
Journal:  Inorg Chem       Date:  2006-04-17       Impact factor: 5.165

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total

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