Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104008509/de1235sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104008509/de1235Isup2.hkl |
CCDC reference: 243581
Me2NCN (0.233 ml, 2.88 mmol) was added by syringe to a solution of the dilithium salt Li2[(1R,2R)-(-)-1,2-(NSiMe3)2C6H10 (0.39 g, 1.44 mmol) in hexane (ca 25 ml) at 273 K. The mixture was slowly warmed to ambient temperature and stirred for a further 12 h. After filtering and vacuum evaporation, the reaction afforded a colourless crystalline product, (I), in moderate yield (0.213 g, 44.5%).
All H atoms were initially located in a difference Fourier map. The methyl H atoms were then constrained to an ideal geometry, with C—H distances of 0.98 Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about its C—C bond. All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.95–1.00 Å and Uiso(H) = 1.2Ueq(C). The Friedel pairs were merged in the refinement. The determination of the absolute configuration was possible from the known (R,R) configuration of the initial lithium salt (Li Weng Wei & Liu, 2002). Furthermore, the Flack parameter (Flack, 1983) of the compound [(1R,2R)-(-)-1,2-(NSiMe3)2-C6H10]2Zr, derived from the same initial lithium salt, has been determined at 0.03 (Li Weng Huang et al., 2002a). Please check added references - the original format was not clear.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Please provide reference); software used to prepare material for publication: SHELXTL.
[Li4(C21H46N8Si2)2] | Z = 1 |
Mr = 961.44 | F(000) = 524 |
Triclinic, P1 | Dx = 1.12 Mg m−3 |
a = 9.4773 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.8506 (19) Å | Cell parameters from 3715 reflections |
c = 15.437 (3) Å | θ = 2.4–25.9° |
α = 100.075 (2)° | µ = 0.15 mm−1 |
β = 104.700 (2)° | T = 190 K |
γ = 105.896 (2)° | Block, colourless |
V = 1424.9 (4) Å3 | 0.2 × 0.2 × 0.1 mm |
Siemens SMART CCD area-detector diffractometer | 5429 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ω scans | θmax = 25°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→9 |
Tmin = 0.971, Tmax = 0.985 | k = −12→12 |
6983 measured reflections | l = −18→18 |
5017 independent reflections |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.026P)2 + 3.2074P] where P = (Fo2 + 2Fc2)/3 |
5898 reflections | (Δ/σ)max = 0.005 |
619 parameters | Δρmax = 0.42 e Å−3 |
3 restraints | Δρmin = −0.40 e Å−3 |
[Li4(C21H46N8Si2)2] | γ = 105.896 (2)° |
Mr = 961.44 | V = 1424.9 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 9.4773 (16) Å | Mo Kα radiation |
b = 10.8506 (19) Å | µ = 0.15 mm−1 |
c = 15.437 (3) Å | T = 190 K |
α = 100.075 (2)° | 0.2 × 0.2 × 0.1 mm |
β = 104.700 (2)° |
Siemens SMART CCD area-detector diffractometer | 5017 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5429 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.985 | Rint = 0.035 |
6983 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 3 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.42 e Å−3 |
5898 reflections | Δρmin = −0.40 e Å−3 |
619 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 | ||
Li1 | 0.8975 (14) | 0.1739 (11) | 0.6527 (8) | 0.035 (2) | |
Li2 | 0.7775 (15) | 0.0141 (11) | 0.3398 (8) | 0.038 (3) | |
Li3 | 1.0694 (15) | 0.0399 (11) | 0.6509 (8) | 0.037 (3) | |
Li4 | 1.0339 (15) | 0.1890 (11) | 0.3886 (8) | 0.037 (3) | |
Si1 | 0.6174 (2) | −0.1145 (2) | 0.11560 (14) | 0.0431 (5) | |
Si2 | 0.9858 (2) | 0.33141 (17) | 0.22419 (13) | 0.0340 (4) | |
Si3 | 1.0214 (2) | 0.33594 (18) | 0.86761 (13) | 0.0383 (5) | |
Si4 | 1.1627 (2) | −0.06669 (19) | 0.83854 (14) | 0.0388 (5) | |
N1 | 0.7291 (7) | 0.1323 (5) | 0.5314 (4) | 0.0310 (12) | |
N2 | 0.8419 (6) | −0.0224 (5) | 0.6387 (4) | 0.0317 (12) | |
N3 | 0.7749 (7) | −0.1661 (5) | 0.7339 (4) | 0.0359 (13) | |
N4 | 1.0355 (6) | −0.0624 (5) | 0.7420 (4) | 0.0332 (13) | |
N5 | 1.1871 (6) | 0.1781 (5) | 0.5021 (3) | 0.0288 (11) | |
N6 | 0.9811 (6) | −0.0090 (5) | 0.3383 (4) | 0.0292 (12) | |
N7 | 0.9659 (7) | −0.1532 (6) | 0.1984 (4) | 0.0409 (14) | |
N8 | 0.9298 (7) | 0.3001 (5) | 0.3164 (4) | 0.0335 (13) | |
N9 | 0.6907 (7) | 0.3268 (6) | 0.3196 (4) | 0.0375 (14) | |
N10 | 0.8040 (6) | 0.1973 (5) | 0.4071 (3) | 0.0282 (12) | |
N11 | 0.7615 (7) | 0.3463 (5) | 0.5258 (4) | 0.0350 (13) | |
N12 | 1.1432 (7) | 0.2272 (5) | 0.6464 (4) | 0.0305 (12) | |
N13 | 1.3356 (7) | 0.3775 (5) | 0.7839 (4) | 0.0351 (13) | |
N14 | 1.2657 (7) | 0.3965 (5) | 0.5823 (4) | 0.0354 (13) | |
N15 | 1.0679 (7) | 0.3087 (5) | 0.7683 (4) | 0.0326 (12) | |
N18 | 0.7567 (7) | −0.0882 (5) | 0.2176 (4) | 0.0362 (13) | |
C1 | 0.6991 (8) | −0.0855 (6) | 0.5604 (5) | 0.0298 (14) | |
H1 | 0.6111 | −0.0837 | 0.5823 | 0.036* | |
C2 | 0.6778 (8) | −0.2309 (6) | 0.5158 (5) | 0.0317 (14) | |
H2A | 0.7677 | −0.2336 | 0.4973 | 0.038* | |
H2B | 0.6717 | −0.2813 | 0.5616 | 0.038* | |
C3 | 0.5325 (8) | −0.2960 (6) | 0.4311 (5) | 0.0363 (15) | |
H3A | 0.5289 | −0.3846 | 0.403 | 0.044* | |
H3B | 0.4417 | −0.3046 | 0.4509 | 0.044* | |
C4 | 0.5280 (8) | −0.2170 (6) | 0.3595 (5) | 0.0391 (16) | |
H4A | 0.4287 | −0.2552 | 0.3109 | 0.047* | |
H4B | 0.6081 | −0.2211 | 0.3316 | 0.047* | |
C5 | 0.5533 (8) | −0.0710 (6) | 0.4051 (4) | 0.0319 (14) | |
H5A | 0.5573 | −0.0207 | 0.3591 | 0.038* | |
H5B | 0.4659 | −0.0668 | 0.4258 | 0.038* | |
C6 | 0.7022 (8) | −0.0072 (6) | 0.4876 (4) | 0.0288 (14) | |
H6 | 0.7894 | −0.011 | 0.4654 | 0.035* | |
C7 | 0.7657 (8) | 0.2214 (6) | 0.4864 (4) | 0.0305 (14) | |
C8 | 0.6981 (10) | 0.3606 (8) | 0.6018 (5) | 0.047 (2) | |
H8A | 0.6179 | 0.2794 | 0.5943 | 0.071* | |
H8B | 0.6558 | 0.4316 | 0.6017 | 0.071* | |
H8C | 0.7786 | 0.3805 | 0.6596 | 0.071* | |
C9 | 0.8603 (10) | 0.4698 (7) | 0.5177 (5) | 0.0442 (18) | |
H9A | 0.9285 | 0.4509 | 0.4847 | 0.066* | |
H9B | 0.9203 | 0.5269 | 0.5785 | 0.066* | |
H9C | 0.7974 | 0.5131 | 0.4845 | 0.066* | |
C10 | 0.8105 (8) | 0.2784 (6) | 0.3476 (4) | 0.0310 (14) | |
C11 | 0.5407 (9) | 0.2766 (8) | 0.3302 (6) | 0.0456 (18) | |
H11A | 0.532 | 0.1967 | 0.3503 | 0.068* | |
H11B | 0.4619 | 0.2577 | 0.2719 | 0.068* | |
H11C | 0.5282 | 0.3418 | 0.3756 | 0.068* | |
C12 | 0.7127 (11) | 0.4427 (8) | 0.2817 (6) | 0.056 (2) | |
H12A | 0.8199 | 0.48 | 0.2871 | 0.084* | |
H12B | 0.6819 | 0.5079 | 0.3156 | 0.084* | |
H12C | 0.6509 | 0.4162 | 0.2175 | 0.084* | |
C13 | 1.1233 (11) | 0.5036 (7) | 0.2526 (6) | 0.051 (2) | |
H13A | 1.0717 | 0.566 | 0.2656 | 0.077* | |
H13B | 1.1591 | 0.5158 | 0.2008 | 0.077* | |
H13C | 1.2099 | 0.5176 | 0.3061 | 0.077* | |
C14 | 0.8305 (10) | 0.3054 (8) | 0.1137 (5) | 0.053 (2) | |
H14A | 0.7564 | 0.2177 | 0.0975 | 0.08* | |
H14B | 0.8754 | 0.3151 | 0.0651 | 0.08* | |
H14C | 0.7797 | 0.3699 | 0.1217 | 0.08* | |
C15 | 1.0944 (11) | 0.2177 (8) | 0.2005 (6) | 0.053 (2) | |
H15A | 1.1723 | 0.2257 | 0.2569 | 0.08* | |
H15B | 1.1428 | 0.2407 | 0.1552 | 0.08* | |
H15C | 1.0244 | 0.1279 | 0.1772 | 0.08* | |
C16 | 0.9027 (8) | −0.0828 (6) | 0.2506 (5) | 0.0332 (15) | |
C17 | 1.1319 (10) | −0.1110 (8) | 0.2109 (5) | 0.0473 (19) | |
H17A | 1.178 | −0.0179 | 0.2416 | 0.071* | |
H17B | 1.1472 | −0.1271 | 0.1514 | 0.071* | |
H17C | 1.1793 | −0.1602 | 0.2478 | 0.071* | |
C18 | 0.8768 (11) | −0.2749 (8) | 0.1268 (6) | 0.058 (2) | |
H18A | 0.7759 | −0.3087 | 0.1327 | 0.087* | |
H18B | 0.9284 | −0.3392 | 0.1332 | 0.087* | |
H18C | 0.8669 | −0.2578 | 0.067 | 0.087* | |
C19 | 0.4669 (12) | −0.2824 (9) | 0.0848 (6) | 0.072 (3) | |
H19A | 0.509 | −0.3495 | 0.0654 | 0.107* | |
H19B | 0.3787 | −0.288 | 0.0351 | 0.107* | |
H19C | 0.436 | −0.2958 | 0.138 | 0.107* | |
C20 | 0.6840 (11) | −0.0908 (9) | 0.0133 (6) | 0.058 (2) | |
H20A | 0.7732 | −0.0121 | 0.0321 | 0.086* | |
H20B | 0.6024 | −0.0819 | −0.0342 | 0.086* | |
H20C | 0.7103 | −0.1663 | −0.0105 | 0.086* | |
C21 | 0.5126 (11) | 0.0029 (10) | 0.1363 (6) | 0.061 (2) | |
H21A | 0.4507 | −0.0248 | 0.1744 | 0.091* | |
H21B | 0.447 | 0.0042 | 0.078 | 0.091* | |
H21C | 0.5859 | 0.0903 | 0.1672 | 0.091* | |
C22 | 1.0976 (7) | −0.0478 (6) | 0.4003 (4) | 0.0272 (13) | |
H22 | 1.1907 | −0.0305 | 0.3812 | 0.033* | |
C23 | 1.0378 (8) | −0.1947 (6) | 0.3978 (4) | 0.0310 (14) | |
H23A | 1.0111 | −0.2479 | 0.3348 | 0.037* | |
H23B | 0.9445 | −0.2124 | 0.4154 | 0.037* | |
C24 | 1.1565 (9) | −0.2361 (7) | 0.4625 (5) | 0.0381 (16) | |
H24A | 1.1109 | −0.3281 | 0.4618 | 0.046* | |
H24B | 1.2449 | −0.229 | 0.4406 | 0.046* | |
C25 | 1.2100 (9) | −0.1492 (6) | 0.5612 (5) | 0.0369 (16) | |
H25A | 1.2946 | −0.1699 | 0.599 | 0.044* | |
H25B | 1.1257 | −0.1685 | 0.587 | 0.044* | |
C26 | 1.2638 (8) | −0.0010 (6) | 0.5646 (5) | 0.0323 (14) | |
H26A | 1.357 | 0.0207 | 0.547 | 0.039* | |
H26B | 1.2888 | 0.0512 | 0.6277 | 0.039* | |
C27 | 1.1393 (7) | 0.0364 (6) | 0.4995 (4) | 0.0260 (13) | |
H27 | 1.0465 | 0.0149 | 0.5187 | 0.031* | |
C28 | 1.1992 (8) | 0.2623 (6) | 0.5783 (4) | 0.0291 (13) | |
C29 | 1.3336 (10) | 0.4292 (7) | 0.5120 (5) | 0.0455 (19) | |
H29A | 1.3773 | 0.3632 | 0.4929 | 0.068* | |
H29B | 1.4134 | 0.5146 | 0.5367 | 0.068* | |
H29C | 1.2552 | 0.4316 | 0.4595 | 0.068* | |
C30 | 1.2367 (10) | 0.5055 (7) | 0.6351 (5) | 0.0464 (19) | |
H30A | 1.1524 | 0.4711 | 0.6576 | 0.07* | |
H30B | 1.2107 | 0.561 | 0.596 | 0.07* | |
H30C | 1.3279 | 0.5567 | 0.6866 | 0.07* | |
C31 | 1.1844 (8) | 0.3093 (6) | 0.7359 (4) | 0.0283 (14) | |
C32 | 1.4624 (9) | 0.3520 (7) | 0.7568 (5) | 0.0441 (18) | |
H32A | 1.4253 | 0.2666 | 0.7129 | 0.066* | |
H32B | 1.5409 | 0.353 | 0.8106 | 0.066* | |
H32C | 1.5053 | 0.4194 | 0.7289 | 0.066* | |
C33 | 1.3847 (10) | 0.4885 (7) | 0.8654 (5) | 0.0482 (19) | |
H33A | 1.2991 | 0.5183 | 0.8682 | 0.072* | |
H33B | 1.4673 | 0.5599 | 0.8617 | 0.072* | |
H33C | 1.4203 | 0.4606 | 0.9202 | 0.072* | |
C34 | 1.1604 (11) | 0.3288 (9) | 0.9768 (5) | 0.057 (2) | |
H34A | 1.1716 | 0.2427 | 0.9683 | 0.086* | |
H34B | 1.1211 | 0.3449 | 1.0276 | 0.086* | |
H34C | 1.2593 | 0.3953 | 0.99 | 0.086* | |
C35 | 0.9878 (12) | 0.4983 (9) | 0.8931 (6) | 0.061 (2) | |
H35A | 1.085 | 0.5694 | 0.914 | 0.091* | |
H35B | 0.9393 | 0.5015 | 0.9407 | 0.091* | |
H35C | 0.9218 | 0.5074 | 0.8379 | 0.091* | |
C36 | 0.8336 (11) | 0.2034 (8) | 0.8443 (6) | 0.057 (2) | |
H36A | 0.7634 | 0.1989 | 0.7858 | 0.085* | |
H36B | 0.7905 | 0.2231 | 0.8928 | 0.085* | |
H36C | 0.8501 | 0.1196 | 0.8421 | 0.085* | |
C37 | 0.6252 (9) | −0.1534 (7) | 0.7273 (5) | 0.0407 (17) | |
H37A | 0.6274 | −0.0664 | 0.7212 | 0.061* | |
H37B | 0.6001 | −0.1663 | 0.7823 | 0.061* | |
H37C | 0.5484 | −0.2191 | 0.674 | 0.061* | |
C38 | 0.7973 (10) | −0.2802 (7) | 0.7648 (6) | 0.0487 (19) | |
H38A | 0.8803 | −0.3002 | 0.7471 | 0.073* | |
H38B | 0.7039 | −0.3553 | 0.7366 | 0.073* | |
H38C | 0.8225 | −0.2606 | 0.8311 | 0.073* | |
C39 | 1.0953 (11) | −0.0594 (9) | 0.9430 (6) | 0.057 (2) | |
H39A | 1.0262 | −0.0088 | 0.9399 | 0.086* | |
H39B | 1.1829 | −0.0178 | 0.9982 | 0.086* | |
H39C | 1.0422 | −0.1478 | 0.9443 | 0.086* | |
C40 | 1.2242 (11) | −0.2147 (9) | 0.8157 (6) | 0.059 (2) | |
H40A | 1.1381 | −0.2938 | 0.804 | 0.088* | |
H40B | 1.3067 | −0.2096 | 0.8688 | 0.088* | |
H40C | 1.2593 | −0.2172 | 0.7625 | 0.088* | |
C41 | 1.3419 (10) | 0.0785 (8) | 0.8645 (6) | 0.056 (2) | |
H41A | 1.3869 | 0.0671 | 0.8158 | 0.083* | |
H41B | 1.4147 | 0.0844 | 0.9224 | 0.083* | |
H41C | 1.3161 | 0.1584 | 0.8687 | 0.083* | |
C42 | 0.8832 (8) | −0.0853 (6) | 0.7045 (4) | 0.0301 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Li1 | 0.030 (6) | 0.037 (6) | 0.035 (6) | 0.009 (5) | 0.010 (5) | 0.007 (5) |
Li2 | 0.044 (7) | 0.037 (6) | 0.030 (6) | 0.012 (5) | 0.008 (5) | 0.010 (5) |
Li3 | 0.046 (7) | 0.041 (6) | 0.031 (6) | 0.020 (6) | 0.014 (5) | 0.014 (5) |
Li4 | 0.047 (7) | 0.040 (6) | 0.030 (6) | 0.019 (6) | 0.018 (5) | 0.010 (5) |
Si1 | 0.0363 (12) | 0.0523 (12) | 0.0290 (10) | 0.0087 (10) | 0.0031 (9) | 0.0022 (9) |
Si2 | 0.0368 (11) | 0.0392 (10) | 0.0308 (10) | 0.0126 (9) | 0.0139 (9) | 0.0163 (8) |
Si3 | 0.0464 (12) | 0.0396 (11) | 0.0304 (10) | 0.0118 (9) | 0.0181 (9) | 0.0084 (8) |
Si4 | 0.0363 (11) | 0.0485 (12) | 0.0358 (11) | 0.0174 (9) | 0.0085 (9) | 0.0205 (9) |
N1 | 0.034 (3) | 0.034 (3) | 0.026 (3) | 0.011 (2) | 0.009 (2) | 0.012 (2) |
N2 | 0.027 (3) | 0.037 (3) | 0.030 (3) | 0.010 (2) | 0.006 (2) | 0.012 (2) |
N3 | 0.031 (3) | 0.040 (3) | 0.041 (3) | 0.009 (3) | 0.013 (3) | 0.021 (3) |
N4 | 0.025 (3) | 0.040 (3) | 0.030 (3) | 0.007 (2) | 0.004 (2) | 0.011 (2) |
N5 | 0.032 (3) | 0.031 (3) | 0.023 (3) | 0.011 (2) | 0.009 (2) | 0.007 (2) |
N6 | 0.029 (3) | 0.036 (3) | 0.025 (3) | 0.014 (2) | 0.008 (2) | 0.009 (2) |
N7 | 0.043 (4) | 0.045 (3) | 0.031 (3) | 0.016 (3) | 0.012 (3) | −0.004 (3) |
N8 | 0.037 (3) | 0.035 (3) | 0.035 (3) | 0.014 (3) | 0.019 (3) | 0.015 (3) |
N9 | 0.035 (3) | 0.052 (4) | 0.041 (3) | 0.023 (3) | 0.018 (3) | 0.028 (3) |
N10 | 0.036 (3) | 0.033 (3) | 0.020 (3) | 0.013 (2) | 0.013 (2) | 0.009 (2) |
N11 | 0.044 (4) | 0.033 (3) | 0.034 (3) | 0.020 (3) | 0.015 (3) | 0.009 (2) |
N12 | 0.038 (3) | 0.029 (3) | 0.026 (3) | 0.009 (2) | 0.014 (3) | 0.009 (2) |
N13 | 0.033 (3) | 0.033 (3) | 0.034 (3) | 0.008 (3) | 0.008 (3) | 0.006 (2) |
N14 | 0.042 (3) | 0.032 (3) | 0.032 (3) | 0.005 (3) | 0.018 (3) | 0.010 (2) |
N15 | 0.036 (3) | 0.037 (3) | 0.024 (3) | 0.010 (3) | 0.013 (2) | 0.005 (2) |
N18 | 0.032 (3) | 0.043 (3) | 0.030 (3) | 0.012 (3) | 0.006 (3) | 0.005 (3) |
C1 | 0.028 (3) | 0.029 (3) | 0.034 (4) | 0.012 (3) | 0.008 (3) | 0.010 (3) |
C2 | 0.031 (4) | 0.034 (3) | 0.036 (4) | 0.016 (3) | 0.011 (3) | 0.013 (3) |
C3 | 0.035 (4) | 0.030 (3) | 0.035 (4) | 0.004 (3) | 0.009 (3) | 0.001 (3) |
C4 | 0.028 (4) | 0.042 (4) | 0.040 (4) | 0.003 (3) | 0.008 (3) | 0.009 (3) |
C5 | 0.028 (4) | 0.036 (4) | 0.033 (4) | 0.011 (3) | 0.010 (3) | 0.012 (3) |
C6 | 0.032 (4) | 0.029 (3) | 0.031 (3) | 0.011 (3) | 0.012 (3) | 0.017 (3) |
C7 | 0.030 (4) | 0.040 (4) | 0.031 (3) | 0.017 (3) | 0.015 (3) | 0.013 (3) |
C8 | 0.067 (6) | 0.054 (5) | 0.035 (4) | 0.036 (4) | 0.026 (4) | 0.010 (3) |
C9 | 0.052 (5) | 0.037 (4) | 0.043 (4) | 0.011 (4) | 0.019 (4) | 0.008 (3) |
C10 | 0.028 (3) | 0.035 (3) | 0.028 (3) | 0.010 (3) | 0.006 (3) | 0.008 (3) |
C11 | 0.031 (4) | 0.061 (5) | 0.050 (5) | 0.020 (4) | 0.015 (4) | 0.019 (4) |
C12 | 0.079 (6) | 0.075 (6) | 0.059 (5) | 0.057 (5) | 0.039 (5) | 0.051 (5) |
C13 | 0.058 (5) | 0.049 (5) | 0.048 (5) | 0.009 (4) | 0.026 (4) | 0.018 (4) |
C14 | 0.056 (6) | 0.067 (6) | 0.031 (4) | 0.015 (5) | 0.010 (4) | 0.014 (4) |
C15 | 0.076 (6) | 0.066 (5) | 0.042 (5) | 0.039 (5) | 0.035 (5) | 0.026 (4) |
C16 | 0.032 (4) | 0.032 (3) | 0.032 (4) | 0.009 (3) | 0.008 (3) | 0.006 (3) |
C17 | 0.052 (5) | 0.058 (5) | 0.041 (4) | 0.025 (4) | 0.022 (4) | 0.014 (4) |
C18 | 0.069 (6) | 0.046 (5) | 0.051 (5) | 0.021 (4) | 0.010 (5) | 0.003 (4) |
C19 | 0.059 (6) | 0.078 (6) | 0.037 (5) | −0.014 (5) | 0.003 (4) | −0.004 (4) |
C20 | 0.061 (6) | 0.085 (6) | 0.034 (4) | 0.035 (5) | 0.016 (4) | 0.018 (4) |
C21 | 0.048 (5) | 0.092 (7) | 0.037 (5) | 0.028 (5) | 0.006 (4) | 0.010 (4) |
C22 | 0.029 (3) | 0.029 (3) | 0.026 (3) | 0.013 (3) | 0.010 (3) | 0.006 (3) |
C23 | 0.034 (4) | 0.032 (3) | 0.030 (4) | 0.014 (3) | 0.012 (3) | 0.009 (3) |
C24 | 0.044 (4) | 0.035 (4) | 0.036 (4) | 0.013 (3) | 0.013 (3) | 0.012 (3) |
C25 | 0.038 (4) | 0.039 (4) | 0.044 (4) | 0.020 (3) | 0.015 (3) | 0.019 (3) |
C26 | 0.026 (3) | 0.037 (4) | 0.028 (3) | 0.010 (3) | 0.001 (3) | 0.004 (3) |
C27 | 0.028 (3) | 0.026 (3) | 0.024 (3) | 0.008 (3) | 0.008 (3) | 0.007 (2) |
C28 | 0.027 (3) | 0.031 (3) | 0.030 (3) | 0.007 (3) | 0.012 (3) | 0.012 (3) |
C29 | 0.050 (5) | 0.040 (4) | 0.042 (4) | 0.000 (3) | 0.018 (4) | 0.018 (3) |
C30 | 0.054 (5) | 0.040 (4) | 0.046 (5) | 0.016 (4) | 0.016 (4) | 0.012 (3) |
C31 | 0.034 (4) | 0.030 (3) | 0.020 (3) | 0.006 (3) | 0.011 (3) | 0.008 (2) |
C32 | 0.040 (4) | 0.047 (4) | 0.037 (4) | 0.007 (4) | 0.011 (4) | 0.004 (3) |
C33 | 0.044 (5) | 0.047 (4) | 0.038 (4) | 0.001 (4) | 0.013 (4) | −0.004 (3) |
C34 | 0.060 (6) | 0.075 (6) | 0.031 (4) | 0.014 (5) | 0.009 (4) | 0.021 (4) |
C35 | 0.071 (7) | 0.064 (6) | 0.058 (6) | 0.030 (5) | 0.034 (5) | 0.011 (4) |
C36 | 0.058 (6) | 0.053 (5) | 0.058 (5) | 0.007 (4) | 0.029 (5) | 0.012 (4) |
C37 | 0.038 (4) | 0.045 (4) | 0.042 (4) | 0.011 (3) | 0.018 (3) | 0.016 (3) |
C38 | 0.058 (5) | 0.038 (4) | 0.054 (5) | 0.016 (4) | 0.016 (4) | 0.026 (4) |
C39 | 0.050 (5) | 0.082 (6) | 0.037 (4) | 0.011 (5) | 0.015 (4) | 0.023 (4) |
C40 | 0.054 (6) | 0.067 (6) | 0.063 (6) | 0.023 (5) | 0.019 (5) | 0.035 (5) |
C41 | 0.041 (5) | 0.071 (6) | 0.050 (5) | 0.020 (4) | 0.001 (4) | 0.022 (4) |
C42 | 0.031 (4) | 0.035 (3) | 0.025 (3) | 0.007 (3) | 0.011 (3) | 0.014 (3) |
Li1—N2 | 2.007 (12) | C9—H9B | 0.96 |
Li1—N1 | 2.013 (13) | C9—H9C | 0.96 |
Li1—N15 | 2.064 (13) | C11—H11A | 0.96 |
Li1—N12 | 2.273 (13) | C11—H11B | 0.96 |
Li2—N18 | 1.947 (12) | C11—H11C | 0.96 |
Li2—N10 | 1.992 (12) | C12—H12A | 0.96 |
Li2—N6 | 2.018 (14) | C12—H12B | 0.96 |
Li3—N4 | 1.973 (12) | C12—H12C | 0.96 |
Li3—N12 | 1.980 (12) | C13—H13A | 0.96 |
Li3—N2 | 2.023 (14) | C13—H13B | 0.96 |
Li4—N5 | 2.017 (13) | C13—H13C | 0.96 |
Li4—N6 | 2.025 (12) | C14—H14A | 0.96 |
Li4—N8 | 2.056 (13) | C14—H14B | 0.96 |
Li4—N10 | 2.292 (13) | C14—H14C | 0.96 |
Si1—N18 | 1.698 (6) | C15—H15A | 0.96 |
Si1—C21 | 1.850 (9) | C15—H15B | 0.96 |
Si1—C19 | 1.873 (9) | C15—H15C | 0.96 |
Si1—C20 | 1.876 (8) | C17—H17A | 0.96 |
Si2—N8 | 1.697 (5) | C17—H17B | 0.96 |
Si2—C15 | 1.856 (7) | C17—H17C | 0.96 |
Si2—C13 | 1.863 (8) | C18—H18A | 0.96 |
Si2—C14 | 1.867 (8) | C18—H18B | 0.96 |
Si3—N15 | 1.700 (5) | C18—H18C | 0.96 |
Si3—C36 | 1.859 (9) | C19—H19A | 0.96 |
Si3—C35 | 1.867 (8) | C19—H19B | 0.96 |
Si3—C34 | 1.886 (8) | C19—H19C | 0.96 |
Si4—N4 | 1.679 (6) | C20—H20A | 0.96 |
Si4—C40 | 1.861 (8) | C20—H20B | 0.96 |
Si4—C41 | 1.869 (9) | C20—H20C | 0.96 |
Si4—C39 | 1.876 (8) | C21—H21A | 0.96 |
N1—C7 | 1.308 (8) | C21—H21B | 0.96 |
N1—C6 | 1.468 (8) | C21—H21C | 0.96 |
N2—C42 | 1.356 (8) | C22—C23 | 1.528 (8) |
N2—C1 | 1.461 (8) | C22—C27 | 1.530 (8) |
N3—C42 | 1.383 (8) | C22—H22 | 0.98 |
N3—C37 | 1.442 (9) | C23—C24 | 1.526 (9) |
N3—C38 | 1.451 (8) | C23—H23A | 0.97 |
N4—C42 | 1.345 (9) | C23—H23B | 0.97 |
N5—C28 | 1.315 (8) | C24—C25 | 1.520 (10) |
N5—C27 | 1.470 (7) | C24—H24A | 0.97 |
N6—C16 | 1.346 (8) | C24—H24B | 0.97 |
N6—C22 | 1.474 (8) | C25—C26 | 1.536 (9) |
N7—C16 | 1.367 (8) | C25—H25A | 0.97 |
N7—C18 | 1.444 (9) | C25—H25B | 0.97 |
N7—C17 | 1.464 (10) | C26—C27 | 1.539 (8) |
N8—C10 | 1.317 (8) | C26—H26A | 0.97 |
N9—C10 | 1.382 (8) | C26—H26B | 0.97 |
N9—C11 | 1.439 (9) | C27—H27 | 0.98 |
N9—C12 | 1.464 (8) | C29—H29A | 0.96 |
N10—C7 | 1.366 (7) | C29—H29B | 0.96 |
N10—C10 | 1.380 (8) | C29—H29C | 0.96 |
N11—C7 | 1.401 (7) | C30—H30A | 0.96 |
N11—C8 | 1.451 (8) | C30—H30B | 0.96 |
N11—C9 | 1.456 (9) | C30—H30C | 0.96 |
N12—C28 | 1.359 (8) | C32—H32A | 0.96 |
N12—C31 | 1.399 (8) | C32—H32B | 0.96 |
N13—C31 | 1.355 (9) | C32—H32C | 0.96 |
N13—C32 | 1.447 (9) | C33—H33A | 0.96 |
N13—C33 | 1.456 (8) | C33—H33B | 0.96 |
N14—C28 | 1.402 (8) | C33—H33C | 0.96 |
N14—C29 | 1.444 (8) | C34—H34A | 0.96 |
N14—C30 | 1.446 (8) | C34—H34B | 0.96 |
N15—C31 | 1.322 (8) | C34—H34C | 0.96 |
N18—C16 | 1.328 (9) | C35—H35A | 0.96 |
C1—C6 | 1.524 (8) | C35—H35B | 0.96 |
C1—C2 | 1.542 (8) | C35—H35C | 0.96 |
C1—H1 | 0.98 | C36—H36A | 0.96 |
C2—C3 | 1.529 (9) | C36—H36B | 0.96 |
C2—H2A | 0.97 | C36—H36C | 0.96 |
C2—H2B | 0.97 | C37—H37A | 0.96 |
C3—C4 | 1.511 (10) | C37—H37B | 0.96 |
C3—H3A | 0.97 | C37—H37C | 0.96 |
C3—H3B | 0.97 | C38—H38A | 0.96 |
C4—C5 | 1.542 (9) | C38—H38B | 0.96 |
C4—H4A | 0.97 | C38—H38C | 0.96 |
C4—H4B | 0.97 | C39—H39A | 0.96 |
C5—C6 | 1.529 (9) | C39—H39B | 0.96 |
C5—H5A | 0.97 | C39—H39C | 0.96 |
C5—H5B | 0.97 | C40—H40A | 0.96 |
C6—H6 | 0.98 | C40—H40B | 0.96 |
C8—H8A | 0.96 | C40—H40C | 0.96 |
C8—H8B | 0.96 | C41—H41A | 0.96 |
C8—H8C | 0.96 | C41—H41B | 0.96 |
C9—H9A | 0.96 | C41—H41C | 0.96 |
N2—Li1—N1 | 87.7 (5) | Si2—C13—H13A | 109.5 |
N2—Li1—N15 | 121.3 (6) | Si2—C13—H13B | 109.5 |
N1—Li1—N15 | 150.9 (6) | H13A—C13—H13B | 109.5 |
N2—Li1—N12 | 101.3 (5) | Si2—C13—H13C | 109.5 |
N1—Li1—N12 | 116.0 (5) | H13A—C13—H13C | 109.5 |
N15—Li1—N12 | 63.7 (4) | H13B—C13—H13C | 109.5 |
N18—Li2—N10 | 140.8 (7) | Si2—C14—H14A | 109.5 |
N18—Li2—N6 | 69.9 (5) | Si2—C14—H14B | 109.5 |
N10—Li2—N6 | 112.3 (6) | H14A—C14—H14B | 109.5 |
N4—Li3—N12 | 139.2 (6) | Si2—C14—H14C | 109.5 |
N4—Li3—N2 | 70.3 (5) | H14A—C14—H14C | 109.5 |
N12—Li3—N2 | 111.8 (6) | H14B—C14—H14C | 109.5 |
N5—Li4—N6 | 87.8 (5) | Si2—C15—H15A | 109.5 |
N5—Li4—N8 | 149.7 (6) | Si2—C15—H15B | 109.5 |
N6—Li4—N8 | 122.5 (7) | H15A—C15—H15B | 109.5 |
N5—Li4—N10 | 114.8 (5) | Si2—C15—H15C | 109.5 |
N6—Li4—N10 | 100.8 (6) | H15A—C15—H15C | 109.5 |
N8—Li4—N10 | 63.6 (4) | H15B—C15—H15C | 109.5 |
N18—Si1—C21 | 106.7 (3) | N18—C16—N6 | 116.3 (6) |
N18—Si1—C19 | 110.7 (4) | N18—C16—N7 | 121.0 (6) |
C21—Si1—C19 | 104.2 (5) | N6—C16—N7 | 122.6 (6) |
N18—Si1—C20 | 116.8 (4) | N7—C17—H17A | 109.5 |
C21—Si1—C20 | 107.9 (4) | N7—C17—H17B | 109.5 |
C19—Si1—C20 | 109.6 (4) | H17A—C17—H17B | 109.5 |
N8—Si2—C15 | 106.0 (3) | N7—C17—H17C | 109.5 |
N8—Si2—C13 | 111.5 (3) | H17A—C17—H17C | 109.5 |
C15—Si2—C13 | 106.6 (4) | H17B—C17—H17C | 109.5 |
N8—Si2—C14 | 117.4 (4) | N7—C18—H18A | 109.5 |
C15—Si2—C14 | 107.4 (4) | N7—C18—H18B | 109.5 |
C13—Si2—C14 | 107.3 (4) | H18A—C18—H18B | 109.5 |
N15—Si3—C36 | 105.3 (3) | N7—C18—H18C | 109.5 |
N15—Si3—C35 | 111.8 (3) | H18A—C18—H18C | 109.5 |
C36—Si3—C35 | 107.1 (4) | H18B—C18—H18C | 109.5 |
N15—Si3—C34 | 117.4 (4) | Si1—C19—H19A | 109.5 |
C36—Si3—C34 | 107.6 (4) | Si1—C19—H19B | 109.5 |
C35—Si3—C34 | 107.2 (4) | H19A—C19—H19B | 109.5 |
N4—Si4—C40 | 110.5 (4) | Si1—C19—H19C | 109.5 |
N4—Si4—C41 | 106.7 (3) | H19A—C19—H19C | 109.5 |
C40—Si4—C41 | 104.7 (4) | H19B—C19—H19C | 109.5 |
N4—Si4—C39 | 115.1 (4) | Si1—C20—H20A | 109.5 |
C40—Si4—C39 | 110.1 (4) | Si1—C20—H20B | 109.5 |
C41—Si4—C39 | 109.2 (4) | H20A—C20—H20B | 109.5 |
C7—N1—C6 | 118.8 (5) | Si1—C20—H20C | 109.5 |
C7—N1—Li1 | 110.5 (6) | H20A—C20—H20C | 109.5 |
C6—N1—Li1 | 104.1 (5) | H20B—C20—H20C | 109.5 |
C42—N2—C1 | 121.1 (5) | Si1—C21—H21A | 109.5 |
C42—N2—Li1 | 127.8 (6) | Si1—C21—H21B | 109.5 |
C1—N2—Li1 | 106.5 (5) | H21A—C21—H21B | 109.5 |
C42—N2—Li3 | 85.1 (5) | Si1—C21—H21C | 109.5 |
C1—N2—Li3 | 134.3 (5) | H21A—C21—H21C | 109.5 |
Li1—N2—Li3 | 75.4 (5) | H21B—C21—H21C | 109.5 |
C42—N3—C37 | 123.4 (6) | N6—C22—C23 | 111.8 (5) |
C42—N3—C38 | 121.8 (6) | N6—C22—C27 | 108.6 (5) |
C37—N3—C38 | 114.5 (6) | C23—C22—C27 | 109.2 (5) |
C42—N4—Si4 | 140.6 (5) | N6—C22—H22 | 109.1 |
C42—N4—Li3 | 87.4 (5) | C23—C22—H22 | 109.1 |
Si4—N4—Li3 | 129.6 (5) | C27—C22—H22 | 109.1 |
C28—N5—C27 | 117.2 (5) | C22—C23—C24 | 112.5 (6) |
C28—N5—Li4 | 112.6 (5) | C22—C23—H23A | 109.1 |
C27—N5—Li4 | 104.4 (5) | C24—C23—H23A | 109.1 |
C16—N6—C22 | 121.3 (5) | C22—C23—H23B | 109.1 |
C16—N6—Li2 | 85.0 (5) | C24—C23—H23B | 109.1 |
C22—N6—Li2 | 134.7 (5) | H23A—C23—H23B | 107.8 |
C16—N6—Li4 | 127.5 (5) | C25—C24—C23 | 111.1 (5) |
C22—N6—Li4 | 106.4 (5) | C25—C24—H24A | 109.4 |
Li2—N6—Li4 | 75.5 (5) | C23—C24—H24A | 109.4 |
C16—N7—C18 | 123.7 (7) | C25—C24—H24B | 109.4 |
C16—N7—C17 | 122.5 (6) | C23—C24—H24B | 109.4 |
C18—N7—C17 | 113.9 (6) | H24A—C24—H24B | 108 |
C10—N8—Si2 | 143.0 (5) | C24—C25—C26 | 111.6 (5) |
C10—N8—Li4 | 95.5 (5) | C24—C25—H25A | 109.3 |
Si2—N8—Li4 | 116.3 (4) | C26—C25—H25A | 109.3 |
C10—N9—C11 | 124.5 (6) | C24—C25—H25B | 109.3 |
C10—N9—C12 | 121.0 (6) | C26—C25—H25B | 109.3 |
C11—N9—C12 | 114.4 (6) | H25A—C25—H25B | 108 |
C7—N10—C10 | 125.1 (5) | C25—C26—C27 | 112.0 (5) |
C7—N10—Li2 | 121.6 (5) | C25—C26—H26A | 109.2 |
C10—N10—Li2 | 109.5 (5) | C27—C26—H26A | 109.2 |
C7—N10—Li4 | 129.7 (5) | C25—C26—H26B | 109.2 |
C10—N10—Li4 | 83.9 (5) | C27—C26—H26B | 109.2 |
Li2—N10—Li4 | 70.2 (5) | H26A—C26—H26B | 107.9 |
C7—N11—C8 | 118.9 (5) | N5—C27—C22 | 109.9 (5) |
C7—N11—C9 | 123.1 (5) | N5—C27—C26 | 113.2 (5) |
C8—N11—C9 | 114.9 (5) | C22—C27—C26 | 109.1 (5) |
C28—N12—C31 | 124.9 (5) | N5—C27—H27 | 108.2 |
C28—N12—Li3 | 122.0 (5) | C22—C27—H27 | 108.2 |
C31—N12—Li3 | 108.5 (5) | C26—C27—H27 | 108.2 |
C28—N12—Li1 | 129.9 (5) | N5—C28—N12 | 124.5 (6) |
C31—N12—Li1 | 85.1 (5) | N5—C28—N14 | 114.8 (5) |
Li3—N12—Li1 | 70.5 (5) | N12—C28—N14 | 120.6 (5) |
C31—N13—C32 | 123.7 (6) | N14—C29—H29A | 109.5 |
C31—N13—C33 | 122.5 (6) | N14—C29—H29B | 109.5 |
C32—N13—C33 | 113.7 (6) | H29A—C29—H29B | 109.5 |
C28—N14—C29 | 118.7 (5) | N14—C29—H29C | 109.5 |
C28—N14—C30 | 124.8 (6) | H29A—C29—H29C | 109.5 |
C29—N14—C30 | 114.2 (5) | H29B—C29—H29C | 109.5 |
C31—N15—Si3 | 143.3 (5) | N14—C30—H30A | 109.5 |
C31—N15—Li1 | 96.0 (5) | N14—C30—H30B | 109.5 |
Si3—N15—Li1 | 116.9 (4) | H30A—C30—H30B | 109.5 |
C16—N18—Si1 | 140.9 (5) | N14—C30—H30C | 109.5 |
C16—N18—Li2 | 88.5 (6) | H30A—C30—H30C | 109.5 |
Si1—N18—Li2 | 127.7 (5) | H30B—C30—H30C | 109.5 |
N2—C1—C6 | 109.0 (5) | N15—C31—N13 | 125.0 (6) |
N2—C1—C2 | 112.1 (5) | N15—C31—N12 | 115.1 (6) |
C6—C1—C2 | 109.2 (5) | N13—C31—N12 | 119.8 (6) |
N2—C1—H1 | 108.8 | N13—C32—H32A | 109.5 |
C6—C1—H1 | 108.8 | N13—C32—H32B | 109.5 |
C2—C1—H1 | 108.8 | H32A—C32—H32B | 109.5 |
C3—C2—C1 | 112.6 (5) | N13—C32—H32C | 109.5 |
C3—C2—H2A | 109.1 | H32A—C32—H32C | 109.5 |
C1—C2—H2A | 109.1 | H32B—C32—H32C | 109.5 |
C3—C2—H2B | 109.1 | N13—C33—H33A | 109.5 |
C1—C2—H2B | 109.1 | N13—C33—H33B | 109.5 |
H2A—C2—H2B | 107.8 | H33A—C33—H33B | 109.5 |
C4—C3—C2 | 112.1 (6) | N13—C33—H33C | 109.5 |
C4—C3—H3A | 109.2 | H33A—C33—H33C | 109.5 |
C2—C3—H3A | 109.2 | H33B—C33—H33C | 109.5 |
C4—C3—H3B | 109.2 | Si3—C34—H34A | 109.5 |
C2—C3—H3B | 109.2 | Si3—C34—H34B | 109.5 |
H3A—C3—H3B | 107.9 | H34A—C34—H34B | 109.5 |
C3—C4—C5 | 110.3 (6) | Si3—C34—H34C | 109.5 |
C3—C4—H4A | 109.6 | H34A—C34—H34C | 109.5 |
C5—C4—H4A | 109.6 | H34B—C34—H34C | 109.5 |
C3—C4—H4B | 109.6 | Si3—C35—H35A | 109.5 |
C5—C4—H4B | 109.6 | Si3—C35—H35B | 109.5 |
H4A—C4—H4B | 108.1 | H35A—C35—H35B | 109.5 |
C6—C5—C4 | 112.6 (5) | Si3—C35—H35C | 109.5 |
C6—C5—H5A | 109.1 | H35A—C35—H35C | 109.5 |
C4—C5—H5A | 109.1 | H35B—C35—H35C | 109.5 |
C6—C5—H5B | 109.1 | Si3—C36—H36A | 109.5 |
C4—C5—H5B | 109.1 | Si3—C36—H36B | 109.5 |
H5A—C5—H5B | 107.8 | H36A—C36—H36B | 109.5 |
N1—C6—C1 | 109.0 (5) | Si3—C36—H36C | 109.5 |
N1—C6—C5 | 113.4 (5) | H36A—C36—H36C | 109.5 |
C1—C6—C5 | 110.0 (5) | H36B—C36—H36C | 109.5 |
N1—C6—H6 | 108.1 | N3—C37—H37A | 109.5 |
C1—C6—H6 | 108.1 | N3—C37—H37B | 109.5 |
C5—C6—H6 | 108.1 | H37A—C37—H37B | 109.5 |
N1—C7—N10 | 124.0 (6) | N3—C37—H37C | 109.5 |
N1—C7—N11 | 114.5 (5) | H37A—C37—H37C | 109.5 |
N10—C7—N11 | 121.5 (5) | H37B—C37—H37C | 109.5 |
N11—C8—H8A | 109.5 | N3—C38—H38A | 109.5 |
N11—C8—H8B | 109.5 | N3—C38—H38B | 109.5 |
H8A—C8—H8B | 109.5 | H38A—C38—H38B | 109.5 |
N11—C8—H8C | 109.5 | N3—C38—H38C | 109.5 |
H8A—C8—H8C | 109.5 | H38A—C38—H38C | 109.5 |
H8B—C8—H8C | 109.5 | H38B—C38—H38C | 109.5 |
N11—C9—H9A | 109.5 | Si4—C39—H39A | 109.5 |
N11—C9—H9B | 109.5 | Si4—C39—H39B | 109.5 |
H9A—C9—H9B | 109.5 | H39A—C39—H39B | 109.5 |
N11—C9—H9C | 109.5 | Si4—C39—H39C | 109.5 |
H9A—C9—H9C | 109.5 | H39A—C39—H39C | 109.5 |
H9B—C9—H9C | 109.5 | H39B—C39—H39C | 109.5 |
N8—C10—N10 | 117.0 (6) | Si4—C40—H40A | 109.5 |
N8—C10—N9 | 123.1 (6) | Si4—C40—H40B | 109.5 |
N10—C10—N9 | 119.8 (6) | H40A—C40—H40B | 109.5 |
N9—C11—H11A | 109.5 | Si4—C40—H40C | 109.5 |
N9—C11—H11B | 109.5 | H40A—C40—H40C | 109.5 |
H11A—C11—H11B | 109.5 | H40B—C40—H40C | 109.5 |
N9—C11—H11C | 109.5 | Si4—C41—H41A | 109.5 |
H11A—C11—H11C | 109.5 | Si4—C41—H41B | 109.5 |
H11B—C11—H11C | 109.5 | H41A—C41—H41B | 109.5 |
N9—C12—H12A | 109.5 | Si4—C41—H41C | 109.5 |
N9—C12—H12B | 109.5 | H41A—C41—H41C | 109.5 |
H12A—C12—H12B | 109.5 | H41B—C41—H41C | 109.5 |
N9—C12—H12C | 109.5 | N4—C42—N2 | 116.8 (6) |
H12A—C12—H12C | 109.5 | N4—C42—N3 | 121.3 (6) |
H12B—C12—H12C | 109.5 | N2—C42—N3 | 121.9 (6) |
N2—Li1—N1—C7 | −147.9 (5) | Li3—N2—C1—C2 | 70.9 (8) |
N15—Li1—N1—C7 | 35.8 (15) | N2—C1—C2—C3 | −177.4 (5) |
N12—Li1—N1—C7 | −46.4 (7) | C6—C1—C2—C3 | −56.5 (7) |
N2—Li1—N1—C6 | −19.3 (5) | C1—C2—C3—C4 | 54.5 (7) |
N15—Li1—N1—C6 | 164.4 (12) | C2—C3—C4—C5 | −52.1 (8) |
N12—Li1—N1—C6 | 82.2 (6) | C3—C4—C5—C6 | 54.8 (7) |
N1—Li1—N2—C42 | −164.9 (6) | C7—N1—C6—C1 | 166.9 (6) |
N15—Li1—N2—C42 | 13.0 (10) | Li1—N1—C6—C1 | 43.5 (6) |
N12—Li1—N2—C42 | 79.0 (7) | C7—N1—C6—C5 | −70.2 (8) |
N1—Li1—N2—C1 | −9.2 (6) | Li1—N1—C6—C5 | 166.4 (5) |
N15—Li1—N2—C1 | 168.7 (6) | N2—C1—C6—N1 | −54.8 (7) |
N12—Li1—N2—C1 | −125.3 (5) | C2—C1—C6—N1 | −177.6 (5) |
N1—Li1—N2—Li3 | 123.3 (5) | N2—C1—C6—C5 | −179.7 (5) |
N15—Li1—N2—Li3 | −58.8 (7) | C2—C1—C6—C5 | 57.5 (7) |
N12—Li1—N2—Li3 | 7.2 (5) | C4—C5—C6—N1 | 179.5 (5) |
N4—Li3—N2—C42 | −3.6 (4) | C4—C5—C6—C1 | −58.2 (7) |
N12—Li3—N2—C42 | −139.8 (6) | C6—N1—C7—N10 | −10.4 (10) |
N4—Li3—N2—C1 | −133.5 (6) | Li1—N1—C7—N10 | 109.7 (7) |
N12—Li3—N2—C1 | 90.3 (8) | C6—N1—C7—N11 | 169.0 (6) |
N4—Li3—N2—Li1 | 127.5 (5) | Li1—N1—C7—N11 | −70.9 (7) |
N12—Li3—N2—Li1 | −8.7 (6) | C10—N10—C7—N1 | 165.2 (7) |
C40—Si4—N4—C42 | 104.7 (8) | Li2—N10—C7—N1 | 9.4 (10) |
C41—Si4—N4—C42 | −142.0 (8) | Li4—N10—C7—N1 | −80.2 (9) |
C39—Si4—N4—C42 | −20.7 (9) | C10—N10—C7—N11 | −14.2 (10) |
C40—Si4—N4—Li3 | −98.8 (6) | Li2—N10—C7—N11 | −170.0 (7) |
C41—Si4—N4—Li3 | 14.5 (7) | Li4—N10—C7—N11 | 100.4 (8) |
C39—Si4—N4—Li3 | 135.8 (6) | C8—N11—C7—N1 | −8.5 (10) |
N12—Li3—N4—C42 | 104.4 (11) | C9—N11—C7—N1 | 150.3 (7) |
N2—Li3—N4—C42 | 3.6 (4) | C8—N11—C7—N10 | 170.9 (7) |
N12—Li3—N4—Si4 | −60.9 (13) | C9—N11—C7—N10 | −30.2 (10) |
N2—Li3—N4—Si4 | −161.7 (5) | Si2—N8—C10—N10 | 149.2 (6) |
N6—Li4—N5—C28 | −146.2 (5) | Li4—N8—C10—N10 | −1.3 (7) |
N8—Li4—N5—C28 | 34.2 (15) | Si2—N8—C10—N9 | −27.3 (12) |
N10—Li4—N5—C28 | −45.4 (8) | Li4—N8—C10—N9 | −177.7 (7) |
N6—Li4—N5—C27 | −18.1 (5) | C7—N10—C10—N8 | 136.4 (7) |
N8—Li4—N5—C27 | 162.3 (12) | Li2—N10—C10—N8 | −65.3 (8) |
N10—Li4—N5—C27 | 82.8 (6) | Li4—N10—C10—N8 | 1.1 (6) |
N18—Li2—N6—C16 | −2.9 (4) | C7—N10—C10—N9 | −47.0 (10) |
N10—Li2—N6—C16 | −140.8 (6) | Li2—N10—C10—N9 | 111.3 (7) |
N18—Li2—N6—C22 | −133.2 (6) | Li4—N10—C10—N9 | 177.7 (7) |
N10—Li2—N6—C22 | 88.9 (8) | C11—N9—C10—N8 | 161.6 (7) |
N18—Li2—N6—Li4 | 127.9 (5) | C12—N9—C10—N8 | −22.9 (10) |
N10—Li2—N6—Li4 | −10.0 (6) | C11—N9—C10—N10 | −14.8 (10) |
N5—Li4—N6—C16 | −165.2 (6) | C12—N9—C10—N10 | 160.8 (6) |
N8—Li4—N6—C16 | 14.6 (11) | Si1—N18—C16—N6 | 154.8 (6) |
N10—Li4—N6—C16 | 80.0 (7) | Li2—N18—C16—N6 | −4.7 (7) |
N5—Li4—N6—C22 | −10.0 (6) | Si1—N18—C16—N7 | −27.6 (12) |
N8—Li4—N6—C22 | 169.8 (6) | Li2—N18—C16—N7 | 172.9 (7) |
N10—Li4—N6—C22 | −124.8 (5) | C22—N6—C16—N18 | 145.2 (6) |
N5—Li4—N6—Li2 | 122.9 (5) | Li2—N6—C16—N18 | 4.5 (7) |
N8—Li4—N6—Li2 | −57.3 (7) | Li4—N6—C16—N18 | −62.9 (9) |
N10—Li4—N6—Li2 | 8.1 (5) | C22—N6—C16—N7 | −32.4 (10) |
C15—Si2—N8—C10 | −133.3 (8) | Li2—N6—C16—N7 | −173.0 (7) |
C13—Si2—N8—C10 | 111.0 (8) | Li4—N6—C16—N7 | 119.6 (8) |
C14—Si2—N8—C10 | −13.4 (9) | C18—N7—C16—N18 | −27.4 (11) |
C15—Si2—N8—Li4 | 13.4 (6) | C17—N7—C16—N18 | 152.9 (7) |
C13—Si2—N8—Li4 | −102.2 (6) | C18—N7—C16—N6 | 150.1 (7) |
C14—Si2—N8—Li4 | 133.4 (6) | C17—N7—C16—N6 | −29.7 (11) |
N5—Li4—N8—C10 | −93.7 (13) | C16—N6—C22—C23 | −47.0 (8) |
N6—Li4—N8—C10 | 86.8 (7) | Li2—N6—C22—C23 | 70.3 (8) |
N10—Li4—N8—C10 | 0.8 (4) | Li4—N6—C22—C23 | 155.9 (5) |
N5—Li4—N8—Si2 | 105.6 (12) | C16—N6—C22—C27 | −167.6 (6) |
N6—Li4—N8—Si2 | −73.9 (8) | Li2—N6—C22—C27 | −50.3 (9) |
N10—Li4—N8—Si2 | −159.9 (4) | Li4—N6—C22—C27 | 35.3 (6) |
N18—Li2—N10—C7 | 158.7 (10) | N6—C22—C23—C24 | −179.3 (5) |
N6—Li2—N10—C7 | −116.1 (7) | C27—C22—C23—C24 | −59.1 (7) |
N18—Li2—N10—C10 | −0.5 (14) | C22—C23—C24—C25 | 55.1 (7) |
N6—Li2—N10—C10 | 84.7 (7) | C23—C24—C25—C26 | −51.6 (8) |
N18—Li2—N10—Li4 | −76.1 (12) | C24—C25—C26—C27 | 54.2 (7) |
N6—Li2—N10—Li4 | 9.1 (5) | C28—N5—C27—C22 | 167.8 (6) |
N5—Li4—N10—C7 | 14.1 (9) | Li4—N5—C27—C22 | 42.5 (6) |
N6—Li4—N10—C7 | 106.6 (7) | C28—N5—C27—C26 | −69.9 (7) |
N8—Li4—N10—C7 | −132.3 (6) | Li4—N5—C27—C26 | 164.8 (5) |
N5—Li4—N10—C10 | 145.7 (6) | N6—C22—C27—N5 | −54.0 (6) |
N6—Li4—N10—C10 | −121.8 (5) | C23—C22—C27—N5 | −176.2 (5) |
N8—Li4—N10—C10 | −0.7 (4) | N6—C22—C27—C26 | −178.7 (5) |
N5—Li4—N10—Li2 | −101.0 (6) | C23—C22—C27—C26 | 59.2 (7) |
N6—Li4—N10—Li2 | −8.5 (5) | C25—C26—C27—N5 | 179.4 (5) |
N8—Li4—N10—Li2 | 112.6 (5) | C25—C26—C27—C22 | −57.8 (7) |
N4—Li3—N12—C28 | 157.9 (9) | C27—N5—C28—N12 | −13.1 (10) |
N2—Li3—N12—C28 | −117.6 (7) | Li4—N5—C28—N12 | 108.0 (7) |
N4—Li3—N12—C31 | 1.0 (13) | C27—N5—C28—N14 | 171.4 (5) |
N2—Li3—N12—C31 | 85.5 (7) | Li4—N5—C28—N14 | −67.4 (8) |
N4—Li3—N12—Li1 | −76.7 (11) | C31—N12—C28—N5 | 164.7 (6) |
N2—Li3—N12—Li1 | 7.9 (5) | Li3—N12—C28—N5 | 11.7 (10) |
N2—Li1—N12—C28 | 108.3 (6) | Li1—N12—C28—N5 | −78.8 (8) |
N1—Li1—N12—C28 | 15.2 (9) | C31—N12—C28—N14 | −20.1 (10) |
N15—Li1—N12—C28 | −132.3 (6) | Li3—N12—C28—N14 | −173.1 (7) |
N2—Li1—N12—C31 | −119.2 (5) | Li1—N12—C28—N14 | 96.4 (8) |
N1—Li1—N12—C31 | 147.8 (6) | C29—N14—C28—N5 | −8.7 (9) |
N15—Li1—N12—C31 | 0.3 (4) | C30—N14—C28—N5 | 153.4 (7) |
N2—Li1—N12—Li3 | −7.5 (5) | C29—N14—C28—N12 | 175.7 (7) |
N1—Li1—N12—Li3 | −100.6 (6) | C30—N14—C28—N12 | −22.2 (10) |
N15—Li1—N12—Li3 | 111.9 (5) | Si3—N15—C31—N13 | −21.9 (12) |
C36—Si3—N15—C31 | −140.1 (8) | Li1—N15—C31—N13 | −176.6 (7) |
C35—Si3—N15—C31 | 104.0 (8) | Si3—N15—C31—N12 | 155.2 (6) |
C34—Si3—N15—C31 | −20.5 (9) | Li1—N15—C31—N12 | 0.5 (6) |
C36—Si3—N15—Li1 | 11.4 (6) | C32—N13—C31—N15 | 164.1 (6) |
C35—Si3—N15—Li1 | −104.5 (6) | C33—N13—C31—N15 | −19.1 (11) |
C34—Si3—N15—Li1 | 131.0 (5) | C32—N13—C31—N12 | −12.9 (10) |
N2—Li1—N15—C31 | 87.2 (7) | C33—N13—C31—N12 | 163.9 (6) |
N1—Li1—N15—C31 | −97.1 (13) | C28—N12—C31—N15 | 136.0 (6) |
N12—Li1—N15—C31 | −0.3 (4) | Li3—N12—C31—N15 | −68.0 (7) |
N2—Li1—N15—Si3 | −76.2 (7) | Li1—N12—C31—N15 | −0.5 (6) |
N1—Li1—N15—Si3 | 99.5 (13) | C28—N12—C31—N13 | −46.7 (9) |
N12—Li1—N15—Si3 | −163.7 (4) | Li3—N12—C31—N13 | 109.3 (7) |
C21—Si1—N18—C16 | −141.1 (8) | Li1—N12—C31—N13 | 176.8 (6) |
C19—Si1—N18—C16 | 106.1 (9) | Si4—N4—C42—N2 | 156.4 (6) |
C20—Si1—N18—C16 | −20.3 (9) | Li3—N4—C42—N2 | −5.7 (7) |
C21—Si1—N18—Li2 | 12.6 (7) | Si4—N4—C42—N3 | −21.7 (11) |
C19—Si1—N18—Li2 | −100.2 (7) | Li3—N4—C42—N3 | 176.2 (7) |
C20—Si1—N18—Li2 | 133.3 (6) | C1—N2—C42—N4 | 145.6 (6) |
N10—Li2—N18—C16 | 104.0 (12) | Li1—N2—C42—N4 | −61.8 (9) |
N6—Li2—N18—C16 | 3.0 (4) | Li3—N2—C42—N4 | 5.5 (6) |
N10—Li2—N18—Si1 | −59.8 (14) | C1—N2—C42—N3 | −36.2 (9) |
N6—Li2—N18—Si1 | −160.8 (5) | Li1—N2—C42—N3 | 116.3 (8) |
C42—N2—C1—C6 | −166.9 (5) | Li3—N2—C42—N3 | −176.3 (7) |
Li1—N2—C1—C6 | 35.4 (7) | C37—N3—C42—N4 | 153.6 (6) |
Li3—N2—C1—C6 | −50.2 (8) | C38—N3—C42—N4 | −33.3 (10) |
C42—N2—C1—C2 | −45.9 (8) | C37—N3—C42—N2 | −24.5 (10) |
Li1—N2—C1—C2 | 156.4 (5) | C38—N3—C42—N2 | 148.6 (7) |
Experimental details
Crystal data | |
Chemical formula | [Li4(C21H46N8Si2)2] |
Mr | 961.44 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 190 |
a, b, c (Å) | 9.4773 (16), 10.8506 (19), 15.437 (3) |
α, β, γ (°) | 100.075 (2), 104.700 (2), 105.896 (2) |
V (Å3) | 1424.9 (4) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.2 × 0.2 × 0.1 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.971, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6983, 5017, 5429 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.156, 1.14 |
No. of reflections | 5898 |
No. of parameters | 619 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.40 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Please provide reference), SHELXTL.
Li1—N2 | 2.007 (12) | Li3—N12 | 1.980 (12) |
Li1—N1 | 2.013 (13) | Li3—N2 | 2.023 (14) |
Li1—N15 | 2.064 (13) | Li4—N5 | 2.017 (13) |
Li1—N12 | 2.273 (13) | Li4—N6 | 2.025 (12) |
Li2—N18 | 1.947 (12) | Li4—N8 | 2.056 (13) |
Li2—N10 | 1.992 (12) | Li4—N10 | 2.292 (13) |
Li2—N6 | 2.018 (14) | N7—C16 | 1.367 (8) |
Li3—N4 | 1.973 (12) | ||
N1—C7—N10 | 124.0 (6) | N5—C28—N12 | 124.5 (6) |
N8—C10—N10 | 117.0 (6) | N15—C31—N12 | 115.1 (6) |
N18—C16—N6 | 116.3 (6) | N4—C42—N2 | 116.8 (6) |
C1—N2—C42—N4 | 145.6 (6) |
The amidinate ligand remains a noteworthy group for incorporation into a wide variety of transition and main-group metal complexes, as its steric and electronic effects can be manipulated through programmed variation of the substituents (Barker & Kilner, 1994; Edelmann, 1994). The addition reaction of N anions as nucleophiles with nitriles has been proved to be a useful and popular method to reach this kind of ligand (Bambirra et al., 2001; Sanger, 1973). In our previous publications (Li Weng Wei & Liu, 2002; Li Weng Huang et al., 2002a,b), we reported varied benzamidinates templated by [(1R,2R)-(-)-1,2-(NHSiMe3)2-C6H10] and studied their structures formally (Li et al., 2003). In order to conduct a thorough investigation, a novel reaction with non-aromatic dimethylcyanamide as substrate was developed successfully, yielding the title compound, (I), and the results are reported here. \sch
Treatment of Li2[(1R,2R)-(-)-1,2-(NSiMe3)2-C6H10] with two molar equivalents of (Me)2NCN gave a crystalline product, (I). It was initially assumed that a typical double-addition reaction had occurred and given a bridged bis(amidinate) compound, through the mechanism reported by Li et al. (2002) Which reference?. However, spectroscopic characterization of (I) reveals an unexpected η3,η5 dianion, which results from single and double 1,3-migration of the SiMe3 group at the two tails of the diaminocyclohexane. To our knowledge, this is the first example of a bridged amidinate-dicyanamide framework. The presence of the dicyanamide moiety as an η5 anion is interesting for us as it has been shown to be a remarkably versatile building block for the construction of supramolecular architectures, since it may act in a mono-, bi- or tridentate manner (Manson et al., 1999; Batten et al., 1998). Please check rephrasing.
The geometric parameters of (I) are listed in Table 1 and its molecular structure is illustrated in Fig. 1. Dimeric aggregation is revealed with a rigorous C2 symmetry. The central eight-membered Li1/N1/C7/N10/Li4/N5/C28/N12 ring shows a distorted boat-boat conformation and is made up of two dicyanamide fragments, upon which are three other types of rings: two cyclohexane groups in chair conformations, two five-membered envelope rings (C1/C6/N1/Li1/N2 and C27/C22/N6/Li4/N5) and two rhombus (LiN)2 rings (Li4/N6/Li2/N10 and Li1/N12/Li3/N2). These six contiguous rings, with the large central ring, result in the whole molecule forming a molecular cage, with a diameter ranging from 4.595 (Li1—Li4) to 3.862 Å (C7—C28) (Fig. 2).
It should be noted that the Li atoms (Li1 and Li4) on the central ring are four-coordinate and bridging, and the other two (Li2 and Li3) are three-coordinate. The two amidinate angles of N2—C42—N4 [116.8 (6)°] and N18—C16—N6 [116.3 (6)°] are similar to the same angles in dicyanamide fragments bonded to the Li atoms [N12—C31—N15 115.1 (6)° and N10—C10—N8 117.0 (6)°], and they are both substantially narrower than in the remaining dicyanamide N—C—N parts [N5—C28—N12 124.5 (6)° and N1—C7—N10 124.0 (6)°]. In addition, the dihedral angles between the two N—C—N fragments in the dicyanamide anions are similar, at 126.2° (N12—C31—N15 and N5—C28—N12) and 126.9° (N10—C10—N8 and N1—C7—N10).
Study of the bond distances in (I) gives a detailed comprehension of its structure and electronic features. It is observed that the C—N bonds on both amidinate and dicyanamide fragments [for example, C16—N18 1.328 (9) Å and C31—N15 1.322 (8) Å] are shorter than a standard C—N single bond [Lide (1962) pointed out that the standard C—N single- and double-bond lengths are 1.474 and 1.265 Å, respectively] and range from 1.308 (8) to 1.399 (8) Å, indicating some degree of π-electron delocalization in the η3,η5 anions. Meanwhile, the C—N(Me)2 bonds [for example, C16—N7 1.367 (8) Å] are also short, in the range 1.355 (9)–1.401 (8) Å, which is interpreted in terms of p–π conjugation between the lone pairs of electrons on the N atoms and anions. These two kinds of C—N bonds are both intermediate between the standard C—N single- and double-bond distances and this is clearly shown in the following sequence: C═N (standard) < C—N (π-delocalization in η3,5 anions) < C—N(Me)2 (p–π conjugation) < C—N (standard).