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The molecular structure of the first anionic bis-COT sandwich compound [COT = cyclo­octatetraene] of the element thulium, of composition [(η8-COT)2Tm][Li(thf)3]+, is reported. It exhibits a weak electrostatic interaction between the lithium ion and two C atoms of one of the COT ligands.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007591/bt6256sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007591/bt6256Isup2.hkl
Contains datablock I

CCDC reference: 214567

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.031
  • wR factor = 0.076
  • Data-to-parameter ratio = 19.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C28 H40 Li1 O3 Tm1 Atom count from _chemical_formula_moiety:

Comment top

We were interested in the accessibility of a mixed COT/terphenyl lanthanide compound. We therefore decided to employ the donor-functionalized terphenyl ligand Danip [Danip = 2,6-di(o-anisol)phenyl] [Rabe et al., 2000; Rabe et al., 2001]. However, the expected terphenyl compound was not obtained, but an anionic bis COT sandwich compound, (I), instead, presumably as a result of a ligand redistribution reaction in which the lithium terphenyl functions solely as the lithium source. The lithium atom is in contact with three tetrahydrofuran ligands, and, additionally, with two of the carbon atoms of one of the COT ligands at distances of 2.346 (7) Å (C1) and 2.606 (7) Å (C8). The calculated distance betwen the thulium and centroids (C1—C8) and (C9—C16) were 1.878 and 1.830 Å, respectively. The molecular structure of the title compound is reminiscent of previously reported anionic bis COT sandwich compounds of other lanthanide elements (Edelmann, 1995; Edelmann et al., 2002). As an example, the molecular structure of the thulium compound can be compared with its samarium analogue [Li(THF)3{µ-(η2:η8-COT)}Sm(η8-COT)] (Wetzel et al., 1999), which features the same chemical composition but a slightly different bonding mode of the lithium counter cation to the bridging COT ligand.

Experimental top

Single crystalline material of [(η8-COT)2Tm][Li(THF)3]+ was obtained in roughly 10% yield from the one-pot reaction of equimolar amounts of DanipLi, TmCl3, and K2COT (Katz, 1960) in tetrahydrofuran at room temperature, followed by extraction of the crude product with toluene and slow evaporation of the solution at ambient temperature. The crystal of was handled under a nitrogen atomosphere, mounted on a glass fiber with Paratone-N oil and then cooled to 150 K.

Refinement top

Hydrogen atoms H1 to H16, which lie in the COT planes, were located in a difference Fourier map. All other hydrogen atoms were placed in calculated postions. All hydrogen atoms Uiso set to 1.2 times that of the connecting atom. Five electron density peaks greater than 1.00 e/Å3 were found within 0.818 Å of the Tm atom.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. Displacement ellipsoids are drawn at the 30% level. Hydrogen atoms are omitted for clarity.
[Figure 2] Fig. 2. Packing diagram, viewed down the b axis of the unit cell.
Bis(cyclooctatetraenyl)thulium lithium tris(tetrahydrofuran) top
Crystal data top
[Li(C4H8O)3(C16H16Tm)]F(000) = 1216
Mr = 600.47Dx = 1.570 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5422 reflections
a = 8.7578 (7) Åθ = 2.3–28.0°
b = 13.9951 (10) ŵ = 3.52 mm1
c = 20.7692 (16) ÅT = 150 K
β = 93.604 (1)°Blocks, red-orange
V = 2540.6 (3) Å30.40 × 0.20 × 0.15 mm
Z = 4
Data collection top
CCD area detector
diffractometer
5717 independent reflections
Radiation source: fine-focus sealed tube5196 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ϕ and ω scansθmax = 27.7°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1111
Tmin = 0.334, Tmax = 0.620k = 1814
15206 measured reflectionsl = 2725
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0449P)2 + 2.8665P]
where P = (Fo2 + 2Fc2)/3
5717 reflections(Δ/σ)max = 0.003
298 parametersΔρmax = 2.13 e Å3
0 restraintsΔρmin = 0.83 e Å3
Crystal data top
[Li(C4H8O)3(C16H16Tm)]V = 2540.6 (3) Å3
Mr = 600.47Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.7578 (7) ŵ = 3.52 mm1
b = 13.9951 (10) ÅT = 150 K
c = 20.7692 (16) Å0.40 × 0.20 × 0.15 mm
β = 93.604 (1)°
Data collection top
CCD area detector
diffractometer
5717 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
5196 reflections with I > 2σ(I)
Tmin = 0.334, Tmax = 0.620Rint = 0.023
15206 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 1.02Δρmax = 2.13 e Å3
5717 reflectionsΔρmin = 0.83 e Å3
298 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
xyzUiso*/Ueq
Tm10.751046 (15)0.721741 (10)0.295265 (7)0.01830 (6)
C10.8076 (5)0.7826 (3)0.41367 (19)0.0276 (8)
H1A0.89110.81570.43480.033*
C20.6949 (4)0.8446 (3)0.38712 (18)0.0286 (8)
H2A0.71850.90990.39560.034*
C30.5547 (4)0.8330 (3)0.35074 (18)0.0289 (8)
H3A0.50630.89230.34040.035*
C40.4689 (4)0.7540 (3)0.32598 (19)0.0291 (8)
H4A0.37820.77260.30170.035*
C50.4873 (4)0.6542 (3)0.32908 (18)0.0295 (8)
H5A0.40470.62110.30720.035*
C60.5986 (4)0.5918 (3)0.35674 (18)0.0288 (8)
H6A0.57370.52650.34920.035*
C70.7388 (4)0.6036 (3)0.39314 (18)0.0272 (8)
H7A0.78550.54420.40480.033*
C80.8259 (4)0.6820 (3)0.41634 (17)0.0266 (8)
H8A0.91860.66330.43910.032*
C91.0142 (4)0.7894 (3)0.2678 (2)0.0290 (8)
H9A1.09470.82130.29190.035*
C100.9054 (5)0.8527 (3)0.23995 (19)0.0314 (9)
H10A0.93040.91760.24910.038*
C110.7680 (4)0.8434 (3)0.20166 (18)0.0320 (9)
H11A0.72250.90330.19060.038*
C120.6820 (5)0.7650 (3)0.17577 (19)0.0319 (9)
H12A0.59070.78450.15220.038*
C130.7004 (5)0.6650 (3)0.17684 (18)0.0321 (8)
H13A0.61980.63290.15290.039*
C140.8097 (5)0.6013 (3)0.20488 (19)0.0328 (9)
H14A0.78490.53640.19600.039*
C150.9472 (4)0.6116 (3)0.24295 (19)0.0301 (8)
H15A0.99340.55200.25400.036*
C161.0323 (4)0.6893 (3)0.26849 (19)0.0289 (8)
H16A1.12390.66980.29180.035*
Li10.7074 (7)0.7621 (4)0.5149 (3)0.0249 (12)
O10.4960 (3)0.73494 (18)0.51695 (15)0.0313 (6)
O20.7321 (3)0.88732 (19)0.55479 (13)0.0310 (6)
O30.8053 (3)0.67676 (19)0.57956 (12)0.0304 (6)
C170.4341 (5)0.6392 (3)0.5143 (2)0.0421 (11)
H17A0.47240.60190.55240.050*
H17B0.46350.60600.47480.050*
C180.2660 (5)0.6502 (3)0.5135 (3)0.0482 (12)
H18A0.23050.64770.55780.058*
H18B0.21380.59940.48730.058*
C190.2357 (5)0.7465 (4)0.4838 (3)0.0502 (12)
H19A0.14100.77510.49910.060*
H19B0.22690.74260.43620.060*
C200.3751 (5)0.8031 (3)0.5073 (2)0.0391 (10)
H20A0.40080.85130.47480.047*
H20B0.35670.83630.54820.047*
C210.8652 (5)0.9450 (3)0.5481 (2)0.0412 (10)
H21A0.85620.98050.50680.049*
H21B0.95770.90430.54850.049*
C220.8768 (5)1.0141 (3)0.6045 (2)0.0374 (9)
H22A0.98331.01870.62320.045*
H22B0.84091.07860.59110.045*
C230.7731 (5)0.9702 (3)0.6519 (2)0.0358 (9)
H23A0.72951.01940.67960.043*
H23B0.82790.92190.67940.043*
C240.6505 (4)0.9245 (3)0.60744 (19)0.0316 (8)
H24A0.59820.87260.62980.038*
H24B0.57360.97240.59190.038*
C250.8716 (5)0.5843 (3)0.5703 (2)0.0354 (9)
H25A0.98470.58830.57420.043*
H25B0.83940.55900.52710.043*
C260.8152 (5)0.5212 (3)0.6218 (2)0.0387 (10)
H26A0.89020.47040.63370.046*
H26B0.71620.49140.60760.046*
C270.7971 (5)0.5885 (3)0.67720 (18)0.0333 (9)
H27A0.89470.59630.70340.040*
H27B0.71750.56570.70530.040*
C280.7490 (5)0.6819 (3)0.64380 (18)0.0326 (9)
H28A0.63620.68850.64130.039*
H28B0.79440.73720.66770.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Tm10.01888 (9)0.01917 (9)0.01739 (9)0.00080 (5)0.00541 (6)0.00131 (5)
C10.0273 (19)0.037 (2)0.0189 (18)0.0089 (16)0.0057 (15)0.0039 (14)
C20.037 (2)0.0251 (18)0.0246 (18)0.0025 (16)0.0118 (16)0.0057 (14)
C30.0305 (19)0.0278 (19)0.0295 (19)0.0120 (16)0.0105 (15)0.0016 (15)
C40.0205 (17)0.041 (2)0.026 (2)0.0040 (16)0.0063 (15)0.0025 (16)
C50.0219 (17)0.040 (2)0.0272 (19)0.0097 (16)0.0045 (15)0.0026 (16)
C60.036 (2)0.0206 (17)0.031 (2)0.0090 (15)0.0138 (16)0.0001 (14)
C70.0319 (19)0.0242 (17)0.0267 (19)0.0034 (15)0.0101 (15)0.0081 (14)
C80.0245 (17)0.040 (2)0.0154 (16)0.0004 (16)0.0011 (13)0.0086 (15)
C90.0235 (18)0.035 (2)0.030 (2)0.0079 (15)0.0115 (15)0.0009 (15)
C100.041 (2)0.0206 (18)0.034 (2)0.0053 (16)0.0148 (17)0.0026 (15)
C110.037 (2)0.032 (2)0.028 (2)0.0101 (17)0.0110 (17)0.0142 (16)
C120.0286 (19)0.051 (3)0.0163 (18)0.0054 (18)0.0043 (15)0.0096 (16)
C130.033 (2)0.045 (2)0.0185 (18)0.0079 (18)0.0050 (15)0.0048 (16)
C140.042 (2)0.0271 (19)0.031 (2)0.0042 (17)0.0171 (17)0.0070 (15)
C150.036 (2)0.0243 (18)0.031 (2)0.0112 (16)0.0163 (17)0.0016 (15)
C160.0198 (17)0.037 (2)0.031 (2)0.0076 (15)0.0073 (15)0.0087 (16)
Li10.024 (3)0.028 (3)0.024 (3)0.001 (2)0.007 (2)0.001 (2)
O10.0234 (13)0.0259 (13)0.0448 (17)0.0052 (11)0.0027 (12)0.0053 (11)
O20.0343 (14)0.0280 (13)0.0323 (15)0.0090 (12)0.0141 (12)0.0075 (11)
O30.0411 (15)0.0265 (14)0.0246 (14)0.0089 (12)0.0098 (11)0.0041 (11)
C170.038 (2)0.030 (2)0.058 (3)0.0099 (18)0.002 (2)0.0034 (19)
C180.041 (2)0.045 (3)0.060 (3)0.015 (2)0.012 (2)0.013 (2)
C190.028 (2)0.054 (3)0.067 (4)0.004 (2)0.010 (2)0.007 (3)
C200.029 (2)0.035 (2)0.053 (3)0.0024 (17)0.0036 (19)0.0053 (19)
C210.041 (2)0.049 (3)0.036 (2)0.020 (2)0.0132 (19)0.0070 (19)
C220.041 (2)0.028 (2)0.042 (2)0.0066 (18)0.0033 (19)0.0050 (17)
C230.039 (2)0.039 (2)0.029 (2)0.0026 (18)0.0026 (17)0.0092 (17)
C240.032 (2)0.032 (2)0.032 (2)0.0023 (16)0.0103 (16)0.0089 (16)
C250.050 (2)0.0253 (19)0.033 (2)0.0073 (17)0.0146 (18)0.0027 (16)
C260.056 (3)0.029 (2)0.032 (2)0.0013 (19)0.0067 (19)0.0020 (16)
C270.045 (2)0.035 (2)0.0213 (18)0.0067 (18)0.0082 (17)0.0038 (15)
C280.038 (2)0.038 (2)0.0228 (19)0.0119 (17)0.0070 (16)0.0045 (16)
Geometric parameters (Å, º) top
Tm1—C92.588 (4)C15—H15A0.9500
Tm1—C102.589 (4)C16—H16A0.9500
Tm1—C122.589 (4)Li1—O11.893 (7)
Tm1—C112.596 (4)Li1—O21.945 (7)
Tm1—C132.596 (4)Li1—O31.955 (7)
Tm1—C152.596 (3)O1—C201.430 (5)
Tm1—C142.598 (4)O1—C171.445 (5)
Tm1—C162.599 (4)O2—C211.432 (5)
Tm1—C82.618 (3)O2—C241.441 (4)
Tm1—C12.620 (4)O3—C251.435 (4)
Tm1—C72.628 (3)O3—C281.453 (4)
Tm1—C42.630 (4)C17—C181.479 (6)
C1—C21.401 (6)C17—H17A0.9900
C1—C81.419 (6)C17—H17B0.9900
C1—Li12.346 (7)C18—C191.499 (7)
C1—H1A0.9500C18—H18A0.9900
C2—C31.410 (6)C18—H18B0.9900
C2—H2A0.9500C19—C201.509 (6)
C3—C41.415 (6)C19—H19A0.9900
C3—H3A0.9500C19—H19B0.9900
C4—C51.407 (6)C20—H20A0.9900
C4—H4A0.9500C20—H20B0.9900
C5—C61.405 (6)C21—C221.517 (6)
C5—H5A0.9500C21—H21A0.9900
C6—C71.410 (6)C21—H21B0.9900
C6—H6A0.9500C22—C231.512 (6)
C7—C81.404 (6)C22—H22A0.9900
C7—H7A0.9500C22—H22B0.9900
C8—Li12.606 (7)C23—C241.512 (6)
C8—H8A0.9500C23—H23A0.9900
C9—C101.399 (6)C23—H23B0.9900
C9—C161.410 (5)C24—H24A0.9900
C9—H9A0.9500C24—H24B0.9900
C10—C111.406 (6)C25—C261.494 (5)
C10—H10A0.9500C25—H25A0.9900
C11—C121.417 (6)C25—H25B0.9900
C11—H11A0.9500C26—C271.503 (5)
C12—C131.410 (6)C26—H26A0.9900
C12—H12A0.9500C26—H26B0.9900
C13—C141.407 (6)C27—C281.526 (5)
C13—H13A0.9500C27—H27A0.9900
C14—C151.406 (6)C27—H27B0.9900
C14—H14A0.9500C28—H28A0.9900
C15—C161.403 (6)C28—H28B0.9900
C9—Tm1—C1031.37 (13)C9—C10—H10A112.3
C9—Tm1—C1282.00 (13)C11—C10—H10A112.3
C10—Tm1—C1260.39 (14)Tm1—C10—H10A135.0
C9—Tm1—C1160.08 (13)C10—C11—C12134.6 (4)
C10—Tm1—C1131.47 (13)C10—C11—Tm174.0 (2)
C12—Tm1—C1131.73 (14)C12—C11—Tm173.9 (2)
C9—Tm1—C1390.26 (13)C10—C11—H11A112.7
C10—Tm1—C1381.90 (13)C12—C11—H11A112.7
C12—Tm1—C1331.56 (14)Tm1—C11—H11A135.8
C11—Tm1—C1360.37 (13)C13—C12—C11134.8 (4)
C9—Tm1—C1560.20 (12)C13—C12—Tm174.5 (2)
C10—Tm1—C1581.76 (12)C11—C12—Tm174.4 (2)
C12—Tm1—C1581.88 (13)C13—C12—H12A112.6
C11—Tm1—C1590.31 (12)C11—C12—H12A112.6
C13—Tm1—C1560.00 (13)Tm1—C12—H12A134.3
C9—Tm1—C1481.88 (13)C14—C13—C12135.2 (4)
C10—Tm1—C1490.35 (12)C14—C13—Tm174.4 (2)
C12—Tm1—C1460.27 (14)C12—C13—Tm173.9 (2)
C11—Tm1—C1482.01 (14)C14—C13—H13A112.4
C13—Tm1—C1431.43 (13)C12—C13—H13A112.4
C15—Tm1—C1431.41 (13)Tm1—C13—H13A135.8
C9—Tm1—C1631.54 (12)C15—C14—C13134.8 (4)
C10—Tm1—C1660.03 (12)C15—C14—Tm174.2 (2)
C12—Tm1—C1690.19 (12)C13—C14—Tm174.2 (2)
C11—Tm1—C1681.65 (12)C15—C14—H14A112.6
C13—Tm1—C1681.46 (13)C13—C14—H14A112.6
C15—Tm1—C1631.33 (13)Tm1—C14—H14A135.0
C14—Tm1—C1659.93 (13)C16—C15—C14135.1 (4)
C9—Tm1—C896.71 (12)C16—C15—Tm174.4 (2)
C10—Tm1—C8118.07 (13)C14—C15—Tm174.4 (2)
C12—Tm1—C8178.44 (12)C16—C15—H15A112.5
C11—Tm1—C8146.73 (13)C14—C15—H15A112.5
C13—Tm1—C8149.58 (14)Tm1—C15—H15A134.7
C15—Tm1—C898.24 (12)C15—C16—C9135.2 (4)
C14—Tm1—C8120.47 (13)C15—C16—Tm174.2 (2)
C16—Tm1—C889.13 (12)C9—C16—Tm173.8 (2)
C9—Tm1—C188.26 (12)C15—C16—H16A112.4
C10—Tm1—C196.50 (12)C9—C16—H16A112.4
C12—Tm1—C1147.40 (13)Tm1—C16—H16A136.2
C11—Tm1—C1118.25 (13)O1—Li1—O2104.7 (3)
C13—Tm1—C1178.39 (12)O1—Li1—O3104.4 (3)
C15—Tm1—C1119.66 (13)O2—Li1—O3103.0 (3)
C14—Tm1—C1148.75 (13)O1—Li1—C1117.8 (3)
C16—Tm1—C197.59 (13)O2—Li1—C1103.5 (3)
C8—Tm1—C131.43 (13)O3—Li1—C1121.2 (3)
C9—Tm1—C7118.75 (13)O1—Li1—C8111.7 (3)
C10—Tm1—C7146.79 (13)O2—Li1—C8133.1 (3)
C12—Tm1—C7150.49 (13)O3—Li1—C895.6 (3)
C11—Tm1—C7177.76 (13)C1—Li1—C832.76 (15)
C13—Tm1—C7121.82 (13)C20—O1—C17109.9 (3)
C15—Tm1—C790.60 (12)C20—O1—Li1125.4 (3)
C14—Tm1—C799.80 (13)C17—O1—Li1123.4 (3)
C16—Tm1—C798.10 (12)C21—O2—C24108.4 (3)
C8—Tm1—C731.05 (12)C21—O2—Li1122.4 (3)
C1—Tm1—C759.55 (12)C24—O2—Li1127.0 (3)
C9—Tm1—C4148.64 (13)C25—O3—C28109.3 (3)
C10—Tm1—C4120.72 (13)C25—O3—Li1128.5 (3)
C12—Tm1—C491.48 (13)C28—O3—Li1116.2 (3)
C11—Tm1—C499.66 (12)O1—C17—C18105.9 (4)
C13—Tm1—C4100.10 (13)O1—C17—H17A110.5
C15—Tm1—C4149.33 (13)C18—C17—H17A110.5
C14—Tm1—C4121.23 (13)O1—C17—H17B110.5
C16—Tm1—C4178.31 (12)C18—C17—H17B110.5
C8—Tm1—C489.19 (12)H17A—C17—H17B108.7
C1—Tm1—C480.87 (13)C17—C18—C19104.4 (4)
C7—Tm1—C480.55 (12)C17—C18—H18A110.9
C2—C1—C8134.9 (4)C19—C18—H18A110.9
C2—C1—Li197.8 (3)C17—C18—H18B110.9
C8—C1—Li183.8 (3)C19—C18—H18B110.9
C2—C1—Tm175.2 (2)H18A—C18—H18B108.9
C8—C1—Tm174.2 (2)C18—C19—C20102.7 (4)
Li1—C1—Tm1137.9 (2)C18—C19—H19A111.2
C2—C1—H1A112.6C20—C19—H19A111.2
C8—C1—H1A112.6C18—C19—H19B111.2
Li1—C1—H1A88.1C20—C19—H19B111.2
Tm1—C1—H1A133.4H19A—C19—H19B109.1
C1—C2—C3135.0 (4)O1—C20—C19105.8 (4)
C1—C2—Tm173.9 (2)O1—C20—H20A110.6
C3—C2—Tm174.5 (2)C19—C20—H20A110.6
C1—C2—H2A112.5O1—C20—H20B110.6
C3—C2—H2A112.5C19—C20—H20B110.6
Tm1—C2—H2A135.5H20A—C20—H20B108.7
C2—C3—C4135.2 (4)O2—C21—C22107.5 (3)
C2—C3—Tm174.5 (2)O2—C21—H21A110.2
C4—C3—Tm174.1 (2)C22—C21—H21A110.2
C2—C3—H3A112.4O2—C21—H21B110.2
C4—C3—H3A112.4C22—C21—H21B110.2
Tm1—C3—H3A135.3H21A—C21—H21B108.5
C5—C4—C3134.6 (4)C23—C22—C21103.2 (3)
C5—C4—Tm174.6 (2)C23—C22—H22A111.1
C3—C4—Tm174.8 (2)C21—C22—H22A111.1
C5—C4—H4A112.7C23—C22—H22B111.1
C3—C4—H4A112.7C21—C22—H22B111.1
Tm1—C4—H4A133.3H22A—C22—H22B109.1
C6—C5—C4135.3 (4)C22—C23—C24102.0 (3)
C6—C5—Tm174.6 (2)C22—C23—H23A111.4
C4—C5—Tm174.4 (2)C24—C23—H23A111.4
C6—C5—H5A112.4C22—C23—H23B111.4
C4—C5—H5A112.4C24—C23—H23B111.4
Tm1—C5—H5A134.6H23A—C23—H23B109.2
C5—C6—C7134.8 (3)O2—C24—C23104.4 (3)
C5—C6—Tm174.5 (2)O2—C24—H24A110.9
C7—C6—Tm174.3 (2)C23—C24—H24A110.9
C5—C6—H6A112.6O2—C24—H24B110.9
C7—C6—H6A112.6C23—C24—H24B110.9
Tm1—C6—H6A134.6H24A—C24—H24B108.9
C8—C7—C6135.3 (3)O3—C25—C26106.4 (3)
C8—C7—Tm174.1 (2)O3—C25—H25A110.4
C6—C7—Tm174.7 (2)C26—C25—H25A110.4
C8—C7—H7A112.3O3—C25—H25B110.4
C6—C7—H7A112.3C26—C25—H25B110.4
Tm1—C7—H7A135.1H25A—C25—H25B108.6
C7—C8—C1134.8 (3)C25—C26—C27103.5 (3)
C7—C8—Li1111.8 (3)C25—C26—H26A111.1
C1—C8—Li163.5 (2)C27—C26—H26A111.1
C7—C8—Tm174.9 (2)C25—C26—H26B111.1
C1—C8—Tm174.4 (2)C27—C26—H26B111.1
Li1—C8—Tm1125.1 (2)H26A—C26—H26B109.0
C7—C8—H8A112.6C26—C27—C28103.2 (3)
C1—C8—H8A112.6C26—C27—H27A111.1
Li1—C8—H8A95.6C28—C27—H27A111.1
Tm1—C8—H8A133.7C26—C27—H27B111.1
C10—C9—C16135.0 (4)C28—C27—H27B111.1
C10—C9—Tm174.3 (2)H27A—C27—H27B109.1
C16—C9—Tm174.7 (2)O3—C28—C27106.0 (3)
C10—C9—H9A112.5O3—C28—H28A110.5
C16—C9—H9A112.5C27—C28—H28A110.5
Tm1—C9—H9A134.2O3—C28—H28B110.5
C9—C10—C11135.3 (4)C27—C28—H28B110.5
C9—C10—Tm174.3 (2)H28A—C28—H28B108.7
C11—C10—Tm174.5 (2)

Experimental details

Crystal data
Chemical formula[Li(C4H8O)3(C16H16Tm)]
Mr600.47
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)8.7578 (7), 13.9951 (10), 20.7692 (16)
β (°) 93.604 (1)
V3)2540.6 (3)
Z4
Radiation typeMo Kα
µ (mm1)3.52
Crystal size (mm)0.40 × 0.20 × 0.15
Data collection
DiffractometerCCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.334, 0.620
No. of measured, independent and
observed [I > 2σ(I)] reflections
15206, 5717, 5196
Rint0.023
(sin θ/λ)max1)0.655
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.076, 1.02
No. of reflections5717
No. of parameters298
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.13, 0.83

Computer programs: SMART (Bruker, 2001), SMART, SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997b), SHELXTL (Bruker, 2001), SHELXTL.

 

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