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The title compound, Li+·HNEt3+·2CF3SO3, is composed of two symmetry-independent tri­fluoro­sulfonate anions, an Li+ cation and a triethyl­ammonium cation. The Li cation is tetrahedrally coordinated by four O atoms from four different CF3SO3 anions. The triethyl­ammonium cation is bonded via an N—H...O hydrogen bond to one of the O atoms that is not coordinating to the Li cation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015241/cv6209sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015241/cv6209Isup2.hkl
Contains datablock I

CCDC reference: 221641

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.029
  • wR factor = 0.058
  • Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5884
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
Li+·C6H16N+·2CF3SO3F(000) = 832
Mr = 407.28Dx = 1.594 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 28862 reflections
a = 10.1400 (13) Åθ = 2.3–24.7°
b = 8.6742 (9) ŵ = 0.40 mm1
c = 19.650 (2) ÅT = 173 K
β = 100.834 (9)°Block, colourless
V = 1697.5 (3) Å30.34 × 0.28 × 0.26 mm
Z = 4
Data collection top
Stoe IPDS-II two-circle
diffractometer
2866 independent reflections
Radiation source: fine-focus sealed tube1690 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
ω scansθmax = 24.7°, θmin = 2.5°
Absorption correction: empirical (using intensity measurements)
(MULABS; Spek, 1990; Blessing, 1995)
h = 1111
Tmin = 0.876, Tmax = 0.903k = 1010
17018 measured reflectionsl = 2223
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058H atoms treated by a mixture of independent and constrained refinement
S = 0.90 w = 1/[σ2(Fo2) + (0.021P)2]
where P = (Fo2 + 2Fc2)/3
2866 reflections(Δ/σ)max = 0.001
221 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Experimental. ;

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
xyzUiso*/Ueq
Li10.5067 (4)0.2469 (4)0.5161 (2)0.0367 (10)
S10.62906 (6)0.02727 (8)0.40908 (3)0.03418 (16)
O110.6343 (2)0.0573 (2)0.33793 (9)0.0544 (5)
O120.56203 (18)0.11409 (19)0.42060 (10)0.0434 (5)
O130.59355 (19)0.1573 (2)0.44703 (10)0.0527 (5)
C10.8032 (3)0.0102 (4)0.44844 (15)0.0482 (7)
F110.88151 (17)0.1094 (2)0.44152 (10)0.0692 (5)
F120.85103 (18)0.1307 (2)0.41999 (11)0.0799 (6)
F130.81498 (17)0.0398 (2)0.51575 (9)0.0765 (6)
S20.69331 (6)0.52177 (7)0.58312 (3)0.03162 (16)
O210.71114 (19)0.5937 (2)0.65035 (9)0.0475 (5)
O220.63628 (18)0.6192 (2)0.52592 (10)0.0460 (5)
O230.63625 (17)0.36949 (19)0.58116 (9)0.0431 (5)
C20.8631 (3)0.4906 (3)0.56913 (14)0.0443 (7)
F210.86174 (17)0.4114 (2)0.51188 (10)0.0806 (6)
F220.92712 (16)0.6210 (2)0.56558 (9)0.0621 (5)
F230.93423 (17)0.4095 (2)0.62142 (11)0.0748 (6)
N10.5314 (2)0.4905 (2)0.73762 (11)0.0357 (5)
H10.580 (2)0.516 (3)0.7093 (13)0.039 (7)*
C110.5259 (3)0.3177 (3)0.73569 (14)0.0379 (6)
H11A0.49630.28390.68710.046*
H11B0.61740.27660.75220.046*
C120.4333 (3)0.2503 (3)0.77892 (16)0.0593 (8)
H12A0.43430.13760.77540.089*
H12B0.34190.28830.76230.089*
H12C0.46310.28090.82740.089*
C210.3969 (3)0.5672 (3)0.71558 (14)0.0464 (7)
H21A0.34030.54420.75020.056*
H21B0.41010.68020.71490.056*
C220.3241 (3)0.5157 (4)0.64502 (13)0.0540 (7)
H22A0.23730.56850.63370.081*
H22B0.30950.40400.64540.081*
H22C0.37820.54110.61020.081*
C310.6028 (3)0.5554 (3)0.80616 (15)0.0525 (8)
H31A0.60210.66940.80320.063*
H31B0.55240.52570.84270.063*
C320.7461 (3)0.5014 (4)0.82716 (15)0.0579 (8)
H32A0.78570.54640.87210.087*
H32B0.79780.53380.79220.087*
H32C0.74780.38870.83080.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Li10.039 (2)0.028 (2)0.043 (3)0.0016 (19)0.009 (2)0.0022 (19)
S10.0392 (4)0.0316 (3)0.0325 (4)0.0035 (3)0.0088 (3)0.0006 (3)
O110.0767 (14)0.0528 (12)0.0344 (10)0.0089 (10)0.0122 (10)0.0066 (9)
O120.0465 (12)0.0378 (10)0.0438 (11)0.0130 (9)0.0034 (9)0.0033 (9)
O130.0566 (13)0.0416 (11)0.0649 (15)0.0026 (10)0.0242 (11)0.0095 (10)
C10.0420 (16)0.0526 (19)0.0530 (19)0.0061 (16)0.0167 (13)0.0056 (16)
F110.0471 (11)0.0777 (12)0.0842 (14)0.0247 (9)0.0160 (10)0.0053 (11)
F120.0612 (12)0.0729 (13)0.1092 (17)0.0205 (10)0.0247 (12)0.0128 (12)
F130.0597 (11)0.1171 (16)0.0468 (11)0.0044 (11)0.0052 (8)0.0182 (11)
S20.0318 (3)0.0338 (4)0.0304 (3)0.0032 (3)0.0089 (3)0.0008 (3)
O210.0565 (11)0.0576 (11)0.0320 (11)0.0143 (10)0.0173 (9)0.0147 (9)
O220.0409 (11)0.0440 (11)0.0520 (12)0.0070 (9)0.0063 (9)0.0140 (9)
O230.0477 (11)0.0378 (10)0.0424 (11)0.0116 (8)0.0051 (9)0.0004 (9)
C20.0424 (16)0.0457 (18)0.0435 (17)0.0071 (15)0.0049 (13)0.0036 (14)
F210.0557 (11)0.1129 (16)0.0795 (14)0.0004 (11)0.0287 (10)0.0441 (12)
F220.0439 (10)0.0731 (12)0.0717 (12)0.0174 (9)0.0170 (9)0.0080 (10)
F230.0475 (10)0.0745 (12)0.0965 (15)0.0123 (9)0.0017 (10)0.0247 (11)
N10.0410 (12)0.0373 (13)0.0316 (11)0.0004 (11)0.0136 (10)0.0007 (10)
C110.0466 (16)0.0310 (13)0.0365 (15)0.0018 (12)0.0088 (12)0.0046 (12)
C120.081 (2)0.0463 (17)0.0542 (19)0.0034 (16)0.0231 (17)0.0114 (15)
C210.0529 (18)0.0449 (18)0.0430 (16)0.0109 (13)0.0132 (14)0.0022 (13)
C220.0519 (16)0.0634 (19)0.0439 (16)0.0126 (16)0.0014 (13)0.0070 (15)
C310.063 (2)0.0457 (18)0.0472 (17)0.0084 (14)0.0061 (14)0.0159 (15)
C320.0575 (19)0.063 (2)0.0476 (17)0.0138 (16)0.0035 (14)0.0033 (16)
Geometric parameters (Å, º) top
Li1—O131.916 (5)N1—C211.506 (3)
Li1—O12i1.920 (4)N1—C311.513 (3)
Li1—O22ii1.919 (4)N1—H10.84 (2)
Li1—O231.964 (4)C11—C121.498 (4)
S1—O111.4331 (18)C11—H11A0.9900
S1—O131.4348 (19)C11—H11B0.9900
S1—O121.4403 (18)C12—H12A0.9800
S1—C11.819 (3)C12—H12B0.9800
O12—Li1i1.920 (4)C12—H12C0.9800
C1—F121.320 (3)C21—C221.511 (4)
C1—F131.331 (3)C21—H21A0.9900
C1—F111.329 (3)C21—H21B0.9900
S2—O221.4380 (18)C22—H22A0.9800
S2—O211.4413 (18)C22—H22B0.9800
S2—O231.4396 (18)C22—H22C0.9800
S2—C21.814 (3)C31—C321.509 (4)
O22—Li1ii1.919 (4)C31—H31A0.9900
C2—F211.316 (3)C31—H31B0.9900
C2—F221.313 (3)C32—H32A0.9800
C2—F231.338 (3)C32—H32B0.9800
N1—C111.501 (3)C32—H32C0.9800
O13—Li1—O12i119.1 (2)C21—N1—H1107.6 (17)
O13—Li1—O22ii110.6 (2)C31—N1—H1104.7 (18)
O12i—Li1—O22ii107.7 (2)C12—C11—N1113.6 (2)
O13—Li1—O23109.9 (2)C12—C11—H11A108.9
O12i—Li1—O23100.5 (2)N1—C11—H11A108.9
O22ii—Li1—O23108.1 (2)C12—C11—H11B108.9
O11—S1—O13115.04 (12)N1—C11—H11B108.9
O11—S1—O12114.40 (12)H11A—C11—H11B107.7
O13—S1—O12114.56 (11)C11—C12—H12A109.5
O11—S1—C1103.64 (12)C11—C12—H12B109.5
O13—S1—C1103.76 (13)H12A—C12—H12B109.5
O12—S1—C1103.32 (12)C11—C12—H12C109.5
S1—O12—Li1i148.45 (17)H12A—C12—H12C109.5
S1—O13—Li1151.73 (17)H12B—C12—H12C109.5
F12—C1—F13107.2 (3)C22—C21—N1113.2 (2)
F12—C1—F11107.5 (2)C22—C21—H21A108.9
F13—C1—F11108.0 (2)N1—C21—H21A108.9
F12—C1—S1111.5 (2)C22—C21—H21B108.9
F13—C1—S1110.81 (18)N1—C21—H21B108.9
F11—C1—S1111.6 (2)H21A—C21—H21B107.8
O22—S2—O21115.13 (12)C21—C22—H22A109.5
O22—S2—O23114.70 (11)C21—C22—H22B109.5
O21—S2—O23113.73 (11)H22A—C22—H22B109.5
O22—S2—C2102.88 (12)C21—C22—H22C109.5
O21—S2—C2104.14 (12)H22A—C22—H22C109.5
O23—S2—C2104.31 (12)H22B—C22—H22C109.5
S2—O22—Li1ii148.46 (18)C32—C31—N1113.7 (2)
S2—O23—Li1136.90 (16)C32—C31—H31A108.8
F21—C2—F22109.3 (2)N1—C31—H31A108.8
F21—C2—F23107.4 (2)C32—C31—H31B108.8
F22—C2—F23107.1 (2)N1—C31—H31B108.8
F21—C2—S2110.45 (18)H31A—C31—H31B107.7
F22—C2—S2111.84 (19)C31—C32—H32A109.5
F23—C2—S2110.59 (19)C31—C32—H32B109.5
C11—N1—C21114.0 (2)H32A—C32—H32B109.5
C11—N1—C31113.8 (2)C31—C32—H32C109.5
C21—N1—C31110.3 (2)H32A—C32—H32C109.5
C11—N1—H1105.6 (18)H32B—C32—H32C109.5
O11—S1—O12—Li1i173.7 (3)O22—S2—O23—Li16.2 (3)
O13—S1—O12—Li1i37.8 (4)O21—S2—O23—Li1141.6 (2)
C1—S1—O12—Li1i74.4 (3)C2—S2—O23—Li1105.6 (3)
O11—S1—O13—Li1144.9 (4)O13—Li1—O23—S281.7 (3)
O12—S1—O13—Li19.3 (4)O12i—Li1—O23—S2151.92 (18)
C1—S1—O13—Li1102.6 (4)O22ii—Li1—O23—S239.1 (3)
O12i—Li1—O13—S110.8 (6)O22—S2—C2—F2165.6 (2)
O22ii—Li1—O13—S1114.8 (4)O21—S2—C2—F21174.0 (2)
O23—Li1—O13—S1125.9 (3)O23—S2—C2—F2154.5 (2)
O11—S1—C1—F1260.9 (2)O22—S2—C2—F2256.4 (2)
O13—S1—C1—F12178.55 (19)O21—S2—C2—F2264.1 (2)
O12—S1—C1—F1258.7 (2)O23—S2—C2—F22176.42 (19)
O11—S1—C1—F13179.7 (2)O22—S2—C2—F23175.61 (19)
O13—S1—C1—F1359.2 (2)O21—S2—C2—F2355.2 (2)
O12—S1—C1—F1360.7 (2)O23—S2—C2—F2364.4 (2)
O11—S1—C1—F1159.3 (2)C21—N1—C11—C1256.9 (3)
O13—S1—C1—F1161.2 (2)C31—N1—C11—C1270.8 (3)
O12—S1—C1—F11178.96 (19)C11—N1—C21—C2254.5 (3)
O21—S2—O22—Li1ii54.5 (4)C31—N1—C21—C22176.0 (2)
O23—S2—O22—Li1ii80.3 (3)C11—N1—C31—C3258.6 (3)
C2—S2—O22—Li1ii167.1 (3)C21—N1—C31—C32171.9 (2)
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O210.84 (2)2.04 (3)2.870 (3)173 (2)
 

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