Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007591/bt6256sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007591/bt6256Isup2.hkl |
CCDC reference: 214567
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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:
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.
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.
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.
[Li(C4H8O)3(C16H16Tm)] | F(000) = 1216 |
Mr = 600.47 | Dx = 1.570 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5422 reflections |
a = 8.7578 (7) Å | θ = 2.3–28.0° |
b = 13.9951 (10) Å | µ = 3.52 mm−1 |
c = 20.7692 (16) Å | T = 150 K |
β = 93.604 (1)° | Blocks, red-orange |
V = 2540.6 (3) Å3 | 0.40 × 0.20 × 0.15 mm |
Z = 4 |
CCD area detector diffractometer | 5717 independent reflections |
Radiation source: fine-focus sealed tube | 5196 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ϕ and ω scans | θmax = 27.7°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −11→11 |
Tmin = 0.334, Tmax = 0.620 | k = −18→14 |
15206 measured reflections | l = −27→25 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.076 | H-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 parameters | Δρmax = 2.13 e Å−3 |
0 restraints | Δρmin = −0.83 e Å−3 |
[Li(C4H8O)3(C16H16Tm)] | V = 2540.6 (3) Å3 |
Mr = 600.47 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.7578 (7) Å | µ = 3.52 mm−1 |
b = 13.9951 (10) Å | T = 150 K |
c = 20.7692 (16) Å | 0.40 × 0.20 × 0.15 mm |
β = 93.604 (1)° |
CCD area detector diffractometer | 5717 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 5196 reflections with I > 2σ(I) |
Tmin = 0.334, Tmax = 0.620 | Rint = 0.023 |
15206 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.076 | H-atom parameters constrained |
S = 1.02 | Δρmax = 2.13 e Å−3 |
5717 reflections | Δρmin = −0.83 e Å−3 |
298 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Tm1 | 0.751046 (15) | 0.721741 (10) | 0.295265 (7) | 0.01830 (6) | |
C1 | 0.8076 (5) | 0.7826 (3) | 0.41367 (19) | 0.0276 (8) | |
H1A | 0.8911 | 0.8157 | 0.4348 | 0.033* | |
C2 | 0.6949 (4) | 0.8446 (3) | 0.38712 (18) | 0.0286 (8) | |
H2A | 0.7185 | 0.9099 | 0.3956 | 0.034* | |
C3 | 0.5547 (4) | 0.8330 (3) | 0.35074 (18) | 0.0289 (8) | |
H3A | 0.5063 | 0.8923 | 0.3404 | 0.035* | |
C4 | 0.4689 (4) | 0.7540 (3) | 0.32598 (19) | 0.0291 (8) | |
H4A | 0.3782 | 0.7726 | 0.3017 | 0.035* | |
C5 | 0.4873 (4) | 0.6542 (3) | 0.32908 (18) | 0.0295 (8) | |
H5A | 0.4047 | 0.6211 | 0.3072 | 0.035* | |
C6 | 0.5986 (4) | 0.5918 (3) | 0.35674 (18) | 0.0288 (8) | |
H6A | 0.5737 | 0.5265 | 0.3492 | 0.035* | |
C7 | 0.7388 (4) | 0.6036 (3) | 0.39314 (18) | 0.0272 (8) | |
H7A | 0.7855 | 0.5442 | 0.4048 | 0.033* | |
C8 | 0.8259 (4) | 0.6820 (3) | 0.41634 (17) | 0.0266 (8) | |
H8A | 0.9186 | 0.6633 | 0.4391 | 0.032* | |
C9 | 1.0142 (4) | 0.7894 (3) | 0.2678 (2) | 0.0290 (8) | |
H9A | 1.0947 | 0.8213 | 0.2919 | 0.035* | |
C10 | 0.9054 (5) | 0.8527 (3) | 0.23995 (19) | 0.0314 (9) | |
H10A | 0.9304 | 0.9176 | 0.2491 | 0.038* | |
C11 | 0.7680 (4) | 0.8434 (3) | 0.20166 (18) | 0.0320 (9) | |
H11A | 0.7225 | 0.9033 | 0.1906 | 0.038* | |
C12 | 0.6820 (5) | 0.7650 (3) | 0.17577 (19) | 0.0319 (9) | |
H12A | 0.5907 | 0.7845 | 0.1522 | 0.038* | |
C13 | 0.7004 (5) | 0.6650 (3) | 0.17684 (18) | 0.0321 (8) | |
H13A | 0.6198 | 0.6329 | 0.1529 | 0.039* | |
C14 | 0.8097 (5) | 0.6013 (3) | 0.20488 (19) | 0.0328 (9) | |
H14A | 0.7849 | 0.5364 | 0.1960 | 0.039* | |
C15 | 0.9472 (4) | 0.6116 (3) | 0.24295 (19) | 0.0301 (8) | |
H15A | 0.9934 | 0.5520 | 0.2540 | 0.036* | |
C16 | 1.0323 (4) | 0.6893 (3) | 0.26849 (19) | 0.0289 (8) | |
H16A | 1.1239 | 0.6698 | 0.2918 | 0.035* | |
Li1 | 0.7074 (7) | 0.7621 (4) | 0.5149 (3) | 0.0249 (12) | |
O1 | 0.4960 (3) | 0.73494 (18) | 0.51695 (15) | 0.0313 (6) | |
O2 | 0.7321 (3) | 0.88732 (19) | 0.55479 (13) | 0.0310 (6) | |
O3 | 0.8053 (3) | 0.67676 (19) | 0.57956 (12) | 0.0304 (6) | |
C17 | 0.4341 (5) | 0.6392 (3) | 0.5143 (2) | 0.0421 (11) | |
H17A | 0.4724 | 0.6019 | 0.5524 | 0.050* | |
H17B | 0.4635 | 0.6060 | 0.4748 | 0.050* | |
C18 | 0.2660 (5) | 0.6502 (3) | 0.5135 (3) | 0.0482 (12) | |
H18A | 0.2305 | 0.6477 | 0.5578 | 0.058* | |
H18B | 0.2138 | 0.5994 | 0.4873 | 0.058* | |
C19 | 0.2357 (5) | 0.7465 (4) | 0.4838 (3) | 0.0502 (12) | |
H19A | 0.1410 | 0.7751 | 0.4991 | 0.060* | |
H19B | 0.2269 | 0.7426 | 0.4362 | 0.060* | |
C20 | 0.3751 (5) | 0.8031 (3) | 0.5073 (2) | 0.0391 (10) | |
H20A | 0.4008 | 0.8513 | 0.4748 | 0.047* | |
H20B | 0.3567 | 0.8363 | 0.5482 | 0.047* | |
C21 | 0.8652 (5) | 0.9450 (3) | 0.5481 (2) | 0.0412 (10) | |
H21A | 0.8562 | 0.9805 | 0.5068 | 0.049* | |
H21B | 0.9577 | 0.9043 | 0.5485 | 0.049* | |
C22 | 0.8768 (5) | 1.0141 (3) | 0.6045 (2) | 0.0374 (9) | |
H22A | 0.9833 | 1.0187 | 0.6232 | 0.045* | |
H22B | 0.8409 | 1.0786 | 0.5911 | 0.045* | |
C23 | 0.7731 (5) | 0.9702 (3) | 0.6519 (2) | 0.0358 (9) | |
H23A | 0.7295 | 1.0194 | 0.6796 | 0.043* | |
H23B | 0.8279 | 0.9219 | 0.6794 | 0.043* | |
C24 | 0.6505 (4) | 0.9245 (3) | 0.60744 (19) | 0.0316 (8) | |
H24A | 0.5982 | 0.8726 | 0.6298 | 0.038* | |
H24B | 0.5736 | 0.9724 | 0.5919 | 0.038* | |
C25 | 0.8716 (5) | 0.5843 (3) | 0.5703 (2) | 0.0354 (9) | |
H25A | 0.9847 | 0.5883 | 0.5742 | 0.043* | |
H25B | 0.8394 | 0.5590 | 0.5271 | 0.043* | |
C26 | 0.8152 (5) | 0.5212 (3) | 0.6218 (2) | 0.0387 (10) | |
H26A | 0.8902 | 0.4704 | 0.6337 | 0.046* | |
H26B | 0.7162 | 0.4914 | 0.6076 | 0.046* | |
C27 | 0.7971 (5) | 0.5885 (3) | 0.67720 (18) | 0.0333 (9) | |
H27A | 0.8947 | 0.5963 | 0.7034 | 0.040* | |
H27B | 0.7175 | 0.5657 | 0.7053 | 0.040* | |
C28 | 0.7490 (5) | 0.6819 (3) | 0.64380 (18) | 0.0326 (9) | |
H28A | 0.6362 | 0.6885 | 0.6413 | 0.039* | |
H28B | 0.7944 | 0.7372 | 0.6677 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Tm1 | 0.01888 (9) | 0.01917 (9) | 0.01739 (9) | 0.00080 (5) | 0.00541 (6) | 0.00131 (5) |
C1 | 0.0273 (19) | 0.037 (2) | 0.0189 (18) | −0.0089 (16) | 0.0057 (15) | −0.0039 (14) |
C2 | 0.037 (2) | 0.0251 (18) | 0.0246 (18) | −0.0025 (16) | 0.0118 (16) | −0.0057 (14) |
C3 | 0.0305 (19) | 0.0278 (19) | 0.0295 (19) | 0.0120 (16) | 0.0105 (15) | 0.0016 (15) |
C4 | 0.0205 (17) | 0.041 (2) | 0.026 (2) | 0.0040 (16) | 0.0063 (15) | 0.0025 (16) |
C5 | 0.0219 (17) | 0.040 (2) | 0.0272 (19) | −0.0097 (16) | 0.0045 (15) | −0.0026 (16) |
C6 | 0.036 (2) | 0.0206 (17) | 0.031 (2) | −0.0090 (15) | 0.0138 (16) | 0.0001 (14) |
C7 | 0.0319 (19) | 0.0242 (17) | 0.0267 (19) | 0.0034 (15) | 0.0101 (15) | 0.0081 (14) |
C8 | 0.0245 (17) | 0.040 (2) | 0.0154 (16) | −0.0004 (16) | 0.0011 (13) | 0.0086 (15) |
C9 | 0.0235 (18) | 0.035 (2) | 0.030 (2) | −0.0079 (15) | 0.0115 (15) | 0.0009 (15) |
C10 | 0.041 (2) | 0.0206 (18) | 0.034 (2) | −0.0053 (16) | 0.0148 (17) | 0.0026 (15) |
C11 | 0.037 (2) | 0.032 (2) | 0.028 (2) | 0.0101 (17) | 0.0110 (17) | 0.0142 (16) |
C12 | 0.0286 (19) | 0.051 (3) | 0.0163 (18) | 0.0054 (18) | 0.0043 (15) | 0.0096 (16) |
C13 | 0.033 (2) | 0.045 (2) | 0.0185 (18) | −0.0079 (18) | 0.0050 (15) | −0.0048 (16) |
C14 | 0.042 (2) | 0.0271 (19) | 0.031 (2) | −0.0042 (17) | 0.0171 (17) | −0.0070 (15) |
C15 | 0.036 (2) | 0.0243 (18) | 0.031 (2) | 0.0112 (16) | 0.0163 (17) | 0.0016 (15) |
C16 | 0.0198 (17) | 0.037 (2) | 0.031 (2) | 0.0076 (15) | 0.0073 (15) | 0.0087 (16) |
Li1 | 0.024 (3) | 0.028 (3) | 0.024 (3) | −0.001 (2) | 0.007 (2) | −0.001 (2) |
O1 | 0.0234 (13) | 0.0259 (13) | 0.0448 (17) | −0.0052 (11) | 0.0027 (12) | 0.0053 (11) |
O2 | 0.0343 (14) | 0.0280 (13) | 0.0323 (15) | −0.0090 (12) | 0.0141 (12) | −0.0075 (11) |
O3 | 0.0411 (15) | 0.0265 (14) | 0.0246 (14) | 0.0089 (12) | 0.0098 (11) | 0.0041 (11) |
C17 | 0.038 (2) | 0.030 (2) | 0.058 (3) | −0.0099 (18) | 0.002 (2) | 0.0034 (19) |
C18 | 0.041 (2) | 0.045 (3) | 0.060 (3) | −0.015 (2) | 0.012 (2) | −0.013 (2) |
C19 | 0.028 (2) | 0.054 (3) | 0.067 (4) | −0.004 (2) | −0.010 (2) | 0.007 (3) |
C20 | 0.029 (2) | 0.035 (2) | 0.053 (3) | 0.0024 (17) | 0.0036 (19) | 0.0053 (19) |
C21 | 0.041 (2) | 0.049 (3) | 0.036 (2) | −0.020 (2) | 0.0132 (19) | −0.0070 (19) |
C22 | 0.041 (2) | 0.028 (2) | 0.042 (2) | −0.0066 (18) | −0.0033 (19) | −0.0050 (17) |
C23 | 0.039 (2) | 0.039 (2) | 0.029 (2) | 0.0026 (18) | 0.0026 (17) | −0.0092 (17) |
C24 | 0.032 (2) | 0.032 (2) | 0.032 (2) | 0.0023 (16) | 0.0103 (16) | −0.0089 (16) |
C25 | 0.050 (2) | 0.0253 (19) | 0.033 (2) | 0.0073 (17) | 0.0146 (18) | 0.0027 (16) |
C26 | 0.056 (3) | 0.029 (2) | 0.032 (2) | 0.0013 (19) | 0.0067 (19) | 0.0020 (16) |
C27 | 0.045 (2) | 0.035 (2) | 0.0213 (18) | 0.0067 (18) | 0.0082 (17) | 0.0038 (15) |
C28 | 0.038 (2) | 0.038 (2) | 0.0228 (19) | 0.0119 (17) | 0.0070 (16) | 0.0045 (16) |
Tm1—C9 | 2.588 (4) | C15—H15A | 0.9500 |
Tm1—C10 | 2.589 (4) | C16—H16A | 0.9500 |
Tm1—C12 | 2.589 (4) | Li1—O1 | 1.893 (7) |
Tm1—C11 | 2.596 (4) | Li1—O2 | 1.945 (7) |
Tm1—C13 | 2.596 (4) | Li1—O3 | 1.955 (7) |
Tm1—C15 | 2.596 (3) | O1—C20 | 1.430 (5) |
Tm1—C14 | 2.598 (4) | O1—C17 | 1.445 (5) |
Tm1—C16 | 2.599 (4) | O2—C21 | 1.432 (5) |
Tm1—C8 | 2.618 (3) | O2—C24 | 1.441 (4) |
Tm1—C1 | 2.620 (4) | O3—C25 | 1.435 (4) |
Tm1—C7 | 2.628 (3) | O3—C28 | 1.453 (4) |
Tm1—C4 | 2.630 (4) | C17—C18 | 1.479 (6) |
C1—C2 | 1.401 (6) | C17—H17A | 0.9900 |
C1—C8 | 1.419 (6) | C17—H17B | 0.9900 |
C1—Li1 | 2.346 (7) | C18—C19 | 1.499 (7) |
C1—H1A | 0.9500 | C18—H18A | 0.9900 |
C2—C3 | 1.410 (6) | C18—H18B | 0.9900 |
C2—H2A | 0.9500 | C19—C20 | 1.509 (6) |
C3—C4 | 1.415 (6) | C19—H19A | 0.9900 |
C3—H3A | 0.9500 | C19—H19B | 0.9900 |
C4—C5 | 1.407 (6) | C20—H20A | 0.9900 |
C4—H4A | 0.9500 | C20—H20B | 0.9900 |
C5—C6 | 1.405 (6) | C21—C22 | 1.517 (6) |
C5—H5A | 0.9500 | C21—H21A | 0.9900 |
C6—C7 | 1.410 (6) | C21—H21B | 0.9900 |
C6—H6A | 0.9500 | C22—C23 | 1.512 (6) |
C7—C8 | 1.404 (6) | C22—H22A | 0.9900 |
C7—H7A | 0.9500 | C22—H22B | 0.9900 |
C8—Li1 | 2.606 (7) | C23—C24 | 1.512 (6) |
C8—H8A | 0.9500 | C23—H23A | 0.9900 |
C9—C10 | 1.399 (6) | C23—H23B | 0.9900 |
C9—C16 | 1.410 (5) | C24—H24A | 0.9900 |
C9—H9A | 0.9500 | C24—H24B | 0.9900 |
C10—C11 | 1.406 (6) | C25—C26 | 1.494 (5) |
C10—H10A | 0.9500 | C25—H25A | 0.9900 |
C11—C12 | 1.417 (6) | C25—H25B | 0.9900 |
C11—H11A | 0.9500 | C26—C27 | 1.503 (5) |
C12—C13 | 1.410 (6) | C26—H26A | 0.9900 |
C12—H12A | 0.9500 | C26—H26B | 0.9900 |
C13—C14 | 1.407 (6) | C27—C28 | 1.526 (5) |
C13—H13A | 0.9500 | C27—H27A | 0.9900 |
C14—C15 | 1.406 (6) | C27—H27B | 0.9900 |
C14—H14A | 0.9500 | C28—H28A | 0.9900 |
C15—C16 | 1.403 (6) | C28—H28B | 0.9900 |
C9—Tm1—C10 | 31.37 (13) | C9—C10—H10A | 112.3 |
C9—Tm1—C12 | 82.00 (13) | C11—C10—H10A | 112.3 |
C10—Tm1—C12 | 60.39 (14) | Tm1—C10—H10A | 135.0 |
C9—Tm1—C11 | 60.08 (13) | C10—C11—C12 | 134.6 (4) |
C10—Tm1—C11 | 31.47 (13) | C10—C11—Tm1 | 74.0 (2) |
C12—Tm1—C11 | 31.73 (14) | C12—C11—Tm1 | 73.9 (2) |
C9—Tm1—C13 | 90.26 (13) | C10—C11—H11A | 112.7 |
C10—Tm1—C13 | 81.90 (13) | C12—C11—H11A | 112.7 |
C12—Tm1—C13 | 31.56 (14) | Tm1—C11—H11A | 135.8 |
C11—Tm1—C13 | 60.37 (13) | C13—C12—C11 | 134.8 (4) |
C9—Tm1—C15 | 60.20 (12) | C13—C12—Tm1 | 74.5 (2) |
C10—Tm1—C15 | 81.76 (12) | C11—C12—Tm1 | 74.4 (2) |
C12—Tm1—C15 | 81.88 (13) | C13—C12—H12A | 112.6 |
C11—Tm1—C15 | 90.31 (12) | C11—C12—H12A | 112.6 |
C13—Tm1—C15 | 60.00 (13) | Tm1—C12—H12A | 134.3 |
C9—Tm1—C14 | 81.88 (13) | C14—C13—C12 | 135.2 (4) |
C10—Tm1—C14 | 90.35 (12) | C14—C13—Tm1 | 74.4 (2) |
C12—Tm1—C14 | 60.27 (14) | C12—C13—Tm1 | 73.9 (2) |
C11—Tm1—C14 | 82.01 (14) | C14—C13—H13A | 112.4 |
C13—Tm1—C14 | 31.43 (13) | C12—C13—H13A | 112.4 |
C15—Tm1—C14 | 31.41 (13) | Tm1—C13—H13A | 135.8 |
C9—Tm1—C16 | 31.54 (12) | C15—C14—C13 | 134.8 (4) |
C10—Tm1—C16 | 60.03 (12) | C15—C14—Tm1 | 74.2 (2) |
C12—Tm1—C16 | 90.19 (12) | C13—C14—Tm1 | 74.2 (2) |
C11—Tm1—C16 | 81.65 (12) | C15—C14—H14A | 112.6 |
C13—Tm1—C16 | 81.46 (13) | C13—C14—H14A | 112.6 |
C15—Tm1—C16 | 31.33 (13) | Tm1—C14—H14A | 135.0 |
C14—Tm1—C16 | 59.93 (13) | C16—C15—C14 | 135.1 (4) |
C9—Tm1—C8 | 96.71 (12) | C16—C15—Tm1 | 74.4 (2) |
C10—Tm1—C8 | 118.07 (13) | C14—C15—Tm1 | 74.4 (2) |
C12—Tm1—C8 | 178.44 (12) | C16—C15—H15A | 112.5 |
C11—Tm1—C8 | 146.73 (13) | C14—C15—H15A | 112.5 |
C13—Tm1—C8 | 149.58 (14) | Tm1—C15—H15A | 134.7 |
C15—Tm1—C8 | 98.24 (12) | C15—C16—C9 | 135.2 (4) |
C14—Tm1—C8 | 120.47 (13) | C15—C16—Tm1 | 74.2 (2) |
C16—Tm1—C8 | 89.13 (12) | C9—C16—Tm1 | 73.8 (2) |
C9—Tm1—C1 | 88.26 (12) | C15—C16—H16A | 112.4 |
C10—Tm1—C1 | 96.50 (12) | C9—C16—H16A | 112.4 |
C12—Tm1—C1 | 147.40 (13) | Tm1—C16—H16A | 136.2 |
C11—Tm1—C1 | 118.25 (13) | O1—Li1—O2 | 104.7 (3) |
C13—Tm1—C1 | 178.39 (12) | O1—Li1—O3 | 104.4 (3) |
C15—Tm1—C1 | 119.66 (13) | O2—Li1—O3 | 103.0 (3) |
C14—Tm1—C1 | 148.75 (13) | O1—Li1—C1 | 117.8 (3) |
C16—Tm1—C1 | 97.59 (13) | O2—Li1—C1 | 103.5 (3) |
C8—Tm1—C1 | 31.43 (13) | O3—Li1—C1 | 121.2 (3) |
C9—Tm1—C7 | 118.75 (13) | O1—Li1—C8 | 111.7 (3) |
C10—Tm1—C7 | 146.79 (13) | O2—Li1—C8 | 133.1 (3) |
C12—Tm1—C7 | 150.49 (13) | O3—Li1—C8 | 95.6 (3) |
C11—Tm1—C7 | 177.76 (13) | C1—Li1—C8 | 32.76 (15) |
C13—Tm1—C7 | 121.82 (13) | C20—O1—C17 | 109.9 (3) |
C15—Tm1—C7 | 90.60 (12) | C20—O1—Li1 | 125.4 (3) |
C14—Tm1—C7 | 99.80 (13) | C17—O1—Li1 | 123.4 (3) |
C16—Tm1—C7 | 98.10 (12) | C21—O2—C24 | 108.4 (3) |
C8—Tm1—C7 | 31.05 (12) | C21—O2—Li1 | 122.4 (3) |
C1—Tm1—C7 | 59.55 (12) | C24—O2—Li1 | 127.0 (3) |
C9—Tm1—C4 | 148.64 (13) | C25—O3—C28 | 109.3 (3) |
C10—Tm1—C4 | 120.72 (13) | C25—O3—Li1 | 128.5 (3) |
C12—Tm1—C4 | 91.48 (13) | C28—O3—Li1 | 116.2 (3) |
C11—Tm1—C4 | 99.66 (12) | O1—C17—C18 | 105.9 (4) |
C13—Tm1—C4 | 100.10 (13) | O1—C17—H17A | 110.5 |
C15—Tm1—C4 | 149.33 (13) | C18—C17—H17A | 110.5 |
C14—Tm1—C4 | 121.23 (13) | O1—C17—H17B | 110.5 |
C16—Tm1—C4 | 178.31 (12) | C18—C17—H17B | 110.5 |
C8—Tm1—C4 | 89.19 (12) | H17A—C17—H17B | 108.7 |
C1—Tm1—C4 | 80.87 (13) | C17—C18—C19 | 104.4 (4) |
C7—Tm1—C4 | 80.55 (12) | C17—C18—H18A | 110.9 |
C2—C1—C8 | 134.9 (4) | C19—C18—H18A | 110.9 |
C2—C1—Li1 | 97.8 (3) | C17—C18—H18B | 110.9 |
C8—C1—Li1 | 83.8 (3) | C19—C18—H18B | 110.9 |
C2—C1—Tm1 | 75.2 (2) | H18A—C18—H18B | 108.9 |
C8—C1—Tm1 | 74.2 (2) | C18—C19—C20 | 102.7 (4) |
Li1—C1—Tm1 | 137.9 (2) | C18—C19—H19A | 111.2 |
C2—C1—H1A | 112.6 | C20—C19—H19A | 111.2 |
C8—C1—H1A | 112.6 | C18—C19—H19B | 111.2 |
Li1—C1—H1A | 88.1 | C20—C19—H19B | 111.2 |
Tm1—C1—H1A | 133.4 | H19A—C19—H19B | 109.1 |
C1—C2—C3 | 135.0 (4) | O1—C20—C19 | 105.8 (4) |
C1—C2—Tm1 | 73.9 (2) | O1—C20—H20A | 110.6 |
C3—C2—Tm1 | 74.5 (2) | C19—C20—H20A | 110.6 |
C1—C2—H2A | 112.5 | O1—C20—H20B | 110.6 |
C3—C2—H2A | 112.5 | C19—C20—H20B | 110.6 |
Tm1—C2—H2A | 135.5 | H20A—C20—H20B | 108.7 |
C2—C3—C4 | 135.2 (4) | O2—C21—C22 | 107.5 (3) |
C2—C3—Tm1 | 74.5 (2) | O2—C21—H21A | 110.2 |
C4—C3—Tm1 | 74.1 (2) | C22—C21—H21A | 110.2 |
C2—C3—H3A | 112.4 | O2—C21—H21B | 110.2 |
C4—C3—H3A | 112.4 | C22—C21—H21B | 110.2 |
Tm1—C3—H3A | 135.3 | H21A—C21—H21B | 108.5 |
C5—C4—C3 | 134.6 (4) | C23—C22—C21 | 103.2 (3) |
C5—C4—Tm1 | 74.6 (2) | C23—C22—H22A | 111.1 |
C3—C4—Tm1 | 74.8 (2) | C21—C22—H22A | 111.1 |
C5—C4—H4A | 112.7 | C23—C22—H22B | 111.1 |
C3—C4—H4A | 112.7 | C21—C22—H22B | 111.1 |
Tm1—C4—H4A | 133.3 | H22A—C22—H22B | 109.1 |
C6—C5—C4 | 135.3 (4) | C22—C23—C24 | 102.0 (3) |
C6—C5—Tm1 | 74.6 (2) | C22—C23—H23A | 111.4 |
C4—C5—Tm1 | 74.4 (2) | C24—C23—H23A | 111.4 |
C6—C5—H5A | 112.4 | C22—C23—H23B | 111.4 |
C4—C5—H5A | 112.4 | C24—C23—H23B | 111.4 |
Tm1—C5—H5A | 134.6 | H23A—C23—H23B | 109.2 |
C5—C6—C7 | 134.8 (3) | O2—C24—C23 | 104.4 (3) |
C5—C6—Tm1 | 74.5 (2) | O2—C24—H24A | 110.9 |
C7—C6—Tm1 | 74.3 (2) | C23—C24—H24A | 110.9 |
C5—C6—H6A | 112.6 | O2—C24—H24B | 110.9 |
C7—C6—H6A | 112.6 | C23—C24—H24B | 110.9 |
Tm1—C6—H6A | 134.6 | H24A—C24—H24B | 108.9 |
C8—C7—C6 | 135.3 (3) | O3—C25—C26 | 106.4 (3) |
C8—C7—Tm1 | 74.1 (2) | O3—C25—H25A | 110.4 |
C6—C7—Tm1 | 74.7 (2) | C26—C25—H25A | 110.4 |
C8—C7—H7A | 112.3 | O3—C25—H25B | 110.4 |
C6—C7—H7A | 112.3 | C26—C25—H25B | 110.4 |
Tm1—C7—H7A | 135.1 | H25A—C25—H25B | 108.6 |
C7—C8—C1 | 134.8 (3) | C25—C26—C27 | 103.5 (3) |
C7—C8—Li1 | 111.8 (3) | C25—C26—H26A | 111.1 |
C1—C8—Li1 | 63.5 (2) | C27—C26—H26A | 111.1 |
C7—C8—Tm1 | 74.9 (2) | C25—C26—H26B | 111.1 |
C1—C8—Tm1 | 74.4 (2) | C27—C26—H26B | 111.1 |
Li1—C8—Tm1 | 125.1 (2) | H26A—C26—H26B | 109.0 |
C7—C8—H8A | 112.6 | C26—C27—C28 | 103.2 (3) |
C1—C8—H8A | 112.6 | C26—C27—H27A | 111.1 |
Li1—C8—H8A | 95.6 | C28—C27—H27A | 111.1 |
Tm1—C8—H8A | 133.7 | C26—C27—H27B | 111.1 |
C10—C9—C16 | 135.0 (4) | C28—C27—H27B | 111.1 |
C10—C9—Tm1 | 74.3 (2) | H27A—C27—H27B | 109.1 |
C16—C9—Tm1 | 74.7 (2) | O3—C28—C27 | 106.0 (3) |
C10—C9—H9A | 112.5 | O3—C28—H28A | 110.5 |
C16—C9—H9A | 112.5 | C27—C28—H28A | 110.5 |
Tm1—C9—H9A | 134.2 | O3—C28—H28B | 110.5 |
C9—C10—C11 | 135.3 (4) | C27—C28—H28B | 110.5 |
C9—C10—Tm1 | 74.3 (2) | H28A—C28—H28B | 108.7 |
C11—C10—Tm1 | 74.5 (2) |
Experimental details
Crystal data | |
Chemical formula | [Li(C4H8O)3(C16H16Tm)] |
Mr | 600.47 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 150 |
a, b, c (Å) | 8.7578 (7), 13.9951 (10), 20.7692 (16) |
β (°) | 93.604 (1) |
V (Å3) | 2540.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.52 |
Crystal size (mm) | 0.40 × 0.20 × 0.15 |
Data collection | |
Diffractometer | CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.334, 0.620 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15206, 5717, 5196 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.655 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.076, 1.02 |
No. of reflections | 5717 |
No. of parameters | 298 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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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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.