Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010353/ac6040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010353/ac6040Isup2.hkl |
CCDC reference: 214781
n-Butyllithium (molar ratio 1:1:1) was added dropwise to a solution of toluene and TMEDA (N,N,N',N'-tetramethylethylenediamine) (molar ratio 1:1:1) in hexane at 273 K and the temperature was allowed to rise to room temperature. The mixture was stirred for more than 24 h and then N,N-dimethyldimethylchlorosilane (molar ratio 1:1) was added at 273 K and the temperature was allowed to rise to room temperature. The mixture was stirred for a further 15 h, yielding a white precipitate (LiCl). The mixture was filtered and N,N-dimethyldimethylbenzylsilylamine was isolated by vacuum distillation of the filtrate as a colorless liquid. A solution of LinBu in hexane was slowly added to N,N-dimethyldimethylbenzylsilylamine and TMEDA in pentane (molar ratio 1:1:1) at ambient temperature. The mixture was stirred for 18 h, ButCN (molar ratio 1:1) was added and stirring was continued for a further 4 h. The solution was concentrated and yielded a colorless crystal of the title compound under vacuum. Crystals suitable for a single-crystal X-ray diffraction study were grown from a concentrated hexane solution at 253 K. All reactions were performed under argon, using standard Schlenk techniques. The hexane was dried by distilling with a sodium–potassium alloy, and the pentane was distilled from a drying agent with sodium.
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 the C—N bond. All other 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 methyl groups (C26, C27 and C28) seem to be disordered but could not be resolved. There are two molecules in the asymmetric unit. Several higher symmetry space groups (P21/c, P21/m, P21/n and P212121) were tried, but none fitted.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
[Li(C16H27N2Si)(C6H16N2)] | F(000) = 880 |
Mr = 398.63 | Dx = 1.028 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 14.819 (3) Å | Cell parameters from 1711 reflections |
b = 9.4142 (16) Å | θ = 2.4–18.0° |
c = 18.635 (3) Å | µ = 0.10 mm−1 |
β = 97.674 (3)° | T = 178 K |
V = 2576.4 (8) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.30 × 0.30 mm |
Bruker CCD area-detector diffractometer | 8386 independent reflections |
Radiation source: oil sealed | 4772 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→16 |
Tmin = 0.960, Tmax = 0.969 | k = −11→11 |
10666 measured reflections | l = −18→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.066 | w = 1/[σ2(Fo2) + (0.0005P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.83 | (Δ/σ)max < 0.001 |
8386 reflections | Δρmax = 0.34 e Å−3 |
527 parameters | Δρmin = −0.25 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (11) |
[Li(C16H27N2Si)(C6H16N2)] | V = 2576.4 (8) Å3 |
Mr = 398.63 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 14.819 (3) Å | µ = 0.10 mm−1 |
b = 9.4142 (16) Å | T = 178 K |
c = 18.635 (3) Å | 0.40 × 0.30 × 0.30 mm |
β = 97.674 (3)° |
Bruker CCD area-detector diffractometer | 8386 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4772 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.969 | Rint = 0.043 |
10666 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.066 | Δρmax = 0.34 e Å−3 |
S = 0.83 | Δρmin = −0.25 e Å−3 |
8386 reflections | Absolute structure: Flack (1983) |
527 parameters | Absolute structure parameter: 0.05 (11) |
1 restraint |
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 | 0.2004 (4) | 0.2342 (7) | 0.2651 (3) | 0.0437 (18) | |
Li2 | 0.6702 (5) | 0.5323 (7) | 0.2263 (4) | 0.0463 (19) | |
Si1 | 0.16518 (8) | 0.38917 (12) | 0.37918 (5) | 0.0365 (3) | |
Si2 | 0.61781 (8) | 0.69132 (11) | 0.10769 (6) | 0.0400 (3) | |
N1 | 0.18673 (19) | 0.2189 (3) | 0.37029 (13) | 0.0302 (8) | |
N2 | 0.2199 (2) | 0.4647 (3) | 0.30983 (16) | 0.0404 (9) | |
N3 | 0.7173 (2) | 0.6236 (3) | 0.14095 (14) | 0.0322 (8) | |
N4 | 0.5430 (2) | 0.6025 (3) | 0.15889 (15) | 0.0404 (9) | |
N5 | 0.1145 (2) | 0.2461 (3) | 0.16363 (15) | 0.0458 (9) | |
N6 | 0.2835 (2) | 0.0980 (3) | 0.21143 (16) | 0.0436 (9) | |
N7 | 0.6742 (3) | 0.5756 (4) | 0.33954 (17) | 0.0540 (10) | |
N8 | 0.7140 (2) | 0.3240 (3) | 0.26068 (17) | 0.0463 (9) | |
C1 | 0.3473 (3) | 0.0256 (4) | 0.42463 (19) | 0.0379 (11) | |
C2 | 0.3865 (3) | 0.1577 (4) | 0.43098 (18) | 0.0407 (11) | |
H2 | 0.3500 | 0.2371 | 0.4343 | 0.049* | |
C3 | 0.4789 (3) | 0.1748 (5) | 0.4325 (2) | 0.0545 (12) | |
H3 | 0.5035 | 0.2657 | 0.4365 | 0.065* | |
C4 | 0.5352 (3) | 0.0614 (5) | 0.4284 (2) | 0.0667 (15) | |
H4 | 0.5974 | 0.0737 | 0.4280 | 0.080* | |
C5 | 0.4968 (3) | −0.0715 (5) | 0.4247 (2) | 0.0699 (15) | |
H5 | 0.5341 | −0.1507 | 0.4235 | 0.084* | |
C6 | 0.4047 (3) | −0.0901 (5) | 0.4228 (2) | 0.0609 (13) | |
H6 | 0.3805 | −0.1814 | 0.4202 | 0.073* | |
C7 | 0.2490 (3) | 0.0004 (4) | 0.42309 (16) | 0.0346 (11) | |
H7 | 0.2330 | −0.0890 | 0.4385 | 0.042* | |
C8 | 0.1783 (3) | 0.0902 (4) | 0.40210 (17) | 0.0297 (10) | |
C9 | 0.0803 (3) | 0.0392 (4) | 0.4110 (2) | 0.0399 (11) | |
C10 | 0.0728 (3) | −0.1177 (4) | 0.43058 (19) | 0.0603 (13) | |
H10A | 0.1054 | −0.1344 | 0.4779 | 0.090* | |
H10B | 0.0982 | −0.1750 | 0.3957 | 0.090* | |
H10C | 0.0098 | −0.1421 | 0.4305 | 0.090* | |
C11 | 0.0487 (2) | 0.1253 (4) | 0.47231 (18) | 0.0538 (12) | |
H11A | 0.0870 | 0.1046 | 0.5168 | 0.081* | |
H11B | −0.0131 | 0.1006 | 0.4770 | 0.081* | |
H11C | 0.0522 | 0.2247 | 0.4617 | 0.081* | |
C12 | 0.0158 (2) | 0.0639 (4) | 0.34123 (18) | 0.0516 (12) | |
H12A | −0.0451 | 0.0395 | 0.3488 | 0.077* | |
H12B | 0.0340 | 0.0055 | 0.3034 | 0.077* | |
H12C | 0.0179 | 0.1620 | 0.3276 | 0.077* | |
C13 | 0.2112 (2) | 0.4694 (4) | 0.46952 (16) | 0.0526 (12) | |
H13A | 0.1795 | 0.4301 | 0.5066 | 0.079* | |
H13B | 0.2027 | 0.5704 | 0.4676 | 0.079* | |
H13C | 0.2750 | 0.4484 | 0.4803 | 0.079* | |
C14 | 0.0453 (2) | 0.4555 (4) | 0.35867 (18) | 0.0500 (12) | |
H14A | 0.0221 | 0.4342 | 0.3092 | 0.075* | |
H14B | 0.0442 | 0.5563 | 0.3661 | 0.075* | |
H14C | 0.0080 | 0.4098 | 0.3902 | 0.075* | |
C15 | 0.3195 (3) | 0.4543 (4) | 0.31790 (19) | 0.0618 (14) | |
H15A | 0.3402 | 0.4723 | 0.2721 | 0.093* | |
H15B | 0.3379 | 0.3607 | 0.3342 | 0.093* | |
H15C | 0.3456 | 0.5231 | 0.3527 | 0.093* | |
C16 | 0.1942 (3) | 0.6088 (4) | 0.28296 (19) | 0.0595 (14) | |
H16A | 0.2181 | 0.6778 | 0.3184 | 0.089* | |
H16B | 0.1291 | 0.6165 | 0.2744 | 0.089* | |
H16C | 0.2188 | 0.6256 | 0.2386 | 0.089* | |
C17 | 0.8072 (3) | 0.4138 (4) | 0.04034 (18) | 0.0330 (10) | |
C18 | 0.8606 (3) | 0.3436 (4) | −0.00472 (19) | 0.0440 (12) | |
H18 | 0.9179 | 0.3799 | −0.0096 | 0.053* | |
C19 | 0.8313 (3) | 0.2214 (4) | −0.0426 (2) | 0.0519 (12) | |
H19 | 0.8684 | 0.1789 | −0.0729 | 0.062* | |
C20 | 0.7486 (3) | 0.1631 (4) | −0.0358 (2) | 0.0598 (13) | |
H20 | 0.7294 | 0.0801 | −0.0603 | 0.072* | |
C21 | 0.6940 (3) | 0.2298 (4) | 0.0082 (2) | 0.0549 (13) | |
H21 | 0.6369 | 0.1926 | 0.0124 | 0.066* | |
C22 | 0.7229 (3) | 0.3508 (4) | 0.04592 (19) | 0.0456 (12) | |
H22 | 0.6851 | 0.3919 | 0.0761 | 0.055* | |
C23 | 0.8421 (2) | 0.5402 (4) | 0.07857 (18) | 0.0359 (10) | |
H23 | 0.9016 | 0.5624 | 0.0722 | 0.043* | |
C24 | 0.8042 (3) | 0.6326 (4) | 0.12200 (19) | 0.0347 (10) | |
C25 | 0.8638 (3) | 0.7587 (4) | 0.1545 (2) | 0.0473 (12) | |
C26 | 0.8430 (4) | 0.7981 (7) | 0.2253 (3) | 0.199 (4) | |
H26A | 0.8628 | 0.7243 | 0.2593 | 0.298* | |
H26B | 0.7784 | 0.8113 | 0.2235 | 0.298* | |
H26C | 0.8738 | 0.8850 | 0.2403 | 0.298* | |
C27 | 0.8404 (4) | 0.8865 (5) | 0.1046 (3) | 0.170 (3) | |
H27A | 0.7788 | 0.8782 | 0.0814 | 0.255* | |
H27B | 0.8809 | 0.8889 | 0.0684 | 0.255* | |
H27C | 0.8470 | 0.9724 | 0.1325 | 0.255* | |
C28 | 0.9637 (3) | 0.7409 (5) | 0.1573 (3) | 0.129 (2) | |
H28A | 0.9941 | 0.8244 | 0.1780 | 0.194* | |
H28B | 0.9786 | 0.7270 | 0.1092 | 0.194* | |
H28C | 0.9832 | 0.6598 | 0.1866 | 0.194* | |
C29 | 0.5846 (3) | 0.6635 (5) | 0.00799 (17) | 0.0780 (16) | |
H29A | 0.6284 | 0.7084 | −0.0181 | 0.117* | |
H29B | 0.5256 | 0.7042 | −0.0066 | 0.117* | |
H29C | 0.5827 | 0.5636 | −0.0024 | 0.117* | |
C30 | 0.5955 (3) | 0.8849 (4) | 0.1215 (2) | 0.0798 (15) | |
H30A | 0.6126 | 0.9089 | 0.1716 | 0.120* | |
H30B | 0.5319 | 0.9043 | 0.1080 | 0.120* | |
H30C | 0.6306 | 0.9406 | 0.0921 | 0.120* | |
C31 | 0.5038 (3) | 0.4692 (4) | 0.1281 (2) | 0.0647 (14) | |
H31A | 0.4553 | 0.4900 | 0.0901 | 0.097* | |
H31B | 0.4805 | 0.4152 | 0.1653 | 0.097* | |
H31C | 0.5501 | 0.4154 | 0.1088 | 0.097* | |
C32 | 0.4702 (3) | 0.6857 (4) | 0.18646 (19) | 0.0642 (13) | |
H32A | 0.4270 | 0.7167 | 0.1465 | 0.096* | |
H32B | 0.4964 | 0.7669 | 0.2126 | 0.096* | |
H32C | 0.4400 | 0.6275 | 0.2182 | 0.096* | |
C33 | 0.1314 (3) | 0.3859 (4) | 0.13395 (19) | 0.0730 (15) | |
H33A | 0.1959 | 0.4017 | 0.1374 | 0.109* | |
H33B | 0.1046 | 0.4579 | 0.1609 | 0.109* | |
H33C | 0.1050 | 0.3900 | 0.0841 | 0.109* | |
C34 | 0.0135 (3) | 0.2265 (5) | 0.16079 (18) | 0.0692 (14) | |
H34A | −0.0145 | 0.2277 | 0.1113 | 0.104* | |
H34B | −0.0110 | 0.3021 | 0.1869 | 0.104* | |
H34C | 0.0015 | 0.1371 | 0.1824 | 0.104* | |
C35 | 0.1476 (3) | 0.1322 (4) | 0.12019 (19) | 0.0597 (14) | |
H35A | 0.1288 | 0.1510 | 0.0692 | 0.072* | |
H35B | 0.1209 | 0.0425 | 0.1321 | 0.072* | |
C36 | 0.2516 (3) | 0.1214 (4) | 0.1346 (2) | 0.0586 (13) | |
H36A | 0.2717 | 0.0435 | 0.1066 | 0.070* | |
H36B | 0.2781 | 0.2082 | 0.1189 | 0.070* | |
C37 | 0.3823 (3) | 0.1157 (4) | 0.22378 (19) | 0.0651 (14) | |
H37A | 0.4103 | 0.0459 | 0.1964 | 0.098* | |
H37B | 0.4037 | 0.1038 | 0.2744 | 0.098* | |
H37C | 0.3979 | 0.2091 | 0.2087 | 0.098* | |
C38 | 0.2609 (3) | −0.0468 (4) | 0.23303 (19) | 0.0637 (14) | |
H38A | 0.1961 | −0.0558 | 0.2309 | 0.096* | |
H38B | 0.2893 | −0.0647 | 0.2816 | 0.096* | |
H38C | 0.2827 | −0.1142 | 0.2007 | 0.096* | |
C39 | 0.7040 (3) | 0.7147 (5) | 0.3694 (2) | 0.0867 (17) | |
H39A | 0.6982 | 0.7172 | 0.4201 | 0.130* | |
H39B | 0.6667 | 0.7877 | 0.3447 | 0.130* | |
H39C | 0.7664 | 0.7301 | 0.3629 | 0.130* | |
C40 | 0.5804 (3) | 0.5531 (4) | 0.35499 (19) | 0.0681 (14) | |
H40A | 0.5551 | 0.4710 | 0.3291 | 0.102* | |
H40B | 0.5442 | 0.6350 | 0.3399 | 0.102* | |
H40C | 0.5808 | 0.5385 | 0.4060 | 0.102* | |
C41 | 0.7354 (3) | 0.4653 (6) | 0.3731 (2) | 0.0784 (17) | |
H41A | 0.7302 | 0.4605 | 0.4244 | 0.094* | |
H41B | 0.7977 | 0.4904 | 0.3681 | 0.094* | |
C42 | 0.7136 (3) | 0.3209 (5) | 0.3392 (2) | 0.0822 (17) | |
H42A | 0.7582 | 0.2523 | 0.3605 | 0.099* | |
H42B | 0.6542 | 0.2903 | 0.3496 | 0.099* | |
C43 | 0.6686 (3) | 0.1982 (4) | 0.2284 (2) | 0.0762 (15) | |
H43A | 0.6689 | 0.2003 | 0.1769 | 0.114* | |
H43B | 0.6069 | 0.1961 | 0.2389 | 0.114* | |
H43C | 0.7001 | 0.1149 | 0.2481 | 0.114* | |
C44 | 0.8084 (3) | 0.3267 (4) | 0.24340 (19) | 0.0610 (14) | |
H44A | 0.8402 | 0.2437 | 0.2632 | 0.092* | |
H44B | 0.8387 | 0.4102 | 0.2640 | 0.092* | |
H44C | 0.8076 | 0.3278 | 0.1918 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Li1 | 0.048 (5) | 0.037 (4) | 0.050 (4) | −0.004 (4) | 0.016 (4) | 0.004 (3) |
Li2 | 0.042 (5) | 0.040 (4) | 0.055 (5) | 0.001 (4) | 0.001 (4) | −0.006 (4) |
Si1 | 0.0368 (7) | 0.0327 (7) | 0.0406 (7) | −0.0008 (6) | 0.0073 (6) | −0.0030 (6) |
Si2 | 0.0365 (8) | 0.0409 (8) | 0.0433 (7) | 0.0014 (6) | 0.0085 (6) | 0.0065 (6) |
N1 | 0.036 (2) | 0.031 (2) | 0.0262 (18) | 0.0012 (17) | 0.0114 (15) | 0.0031 (15) |
N2 | 0.038 (2) | 0.035 (2) | 0.051 (2) | −0.0037 (18) | 0.0133 (19) | 0.0106 (17) |
N3 | 0.025 (2) | 0.0361 (19) | 0.037 (2) | −0.0020 (16) | 0.0097 (17) | −0.0002 (16) |
N4 | 0.034 (2) | 0.042 (2) | 0.048 (2) | −0.0025 (18) | 0.0156 (18) | 0.0018 (18) |
N5 | 0.065 (3) | 0.039 (2) | 0.035 (2) | 0.001 (2) | 0.009 (2) | −0.0025 (18) |
N6 | 0.053 (3) | 0.045 (2) | 0.037 (2) | 0.001 (2) | 0.0201 (19) | −0.0009 (18) |
N7 | 0.057 (3) | 0.068 (3) | 0.039 (2) | −0.008 (2) | 0.014 (2) | −0.006 (2) |
N8 | 0.047 (3) | 0.045 (2) | 0.049 (2) | 0.002 (2) | 0.012 (2) | 0.0019 (18) |
C1 | 0.043 (3) | 0.035 (3) | 0.037 (3) | 0.006 (2) | 0.010 (2) | −0.001 (2) |
C2 | 0.038 (3) | 0.044 (3) | 0.042 (3) | 0.013 (2) | 0.009 (2) | 0.004 (2) |
C3 | 0.048 (3) | 0.054 (3) | 0.060 (3) | 0.001 (3) | 0.003 (3) | 0.005 (3) |
C4 | 0.046 (3) | 0.081 (4) | 0.073 (4) | 0.015 (3) | 0.011 (3) | 0.019 (3) |
C5 | 0.053 (4) | 0.066 (4) | 0.093 (4) | 0.033 (3) | 0.020 (3) | 0.010 (3) |
C6 | 0.062 (4) | 0.049 (3) | 0.072 (3) | 0.011 (3) | 0.012 (3) | 0.006 (3) |
C7 | 0.053 (3) | 0.025 (2) | 0.029 (2) | 0.001 (2) | 0.012 (2) | 0.0088 (18) |
C8 | 0.043 (3) | 0.028 (2) | 0.020 (2) | −0.005 (2) | 0.012 (2) | −0.0034 (18) |
C9 | 0.045 (3) | 0.030 (2) | 0.048 (3) | −0.005 (2) | 0.017 (2) | 0.001 (2) |
C10 | 0.071 (3) | 0.039 (3) | 0.079 (3) | −0.013 (3) | 0.037 (3) | 0.006 (3) |
C11 | 0.047 (3) | 0.057 (3) | 0.062 (3) | −0.004 (2) | 0.023 (2) | 0.003 (2) |
C12 | 0.041 (3) | 0.062 (3) | 0.052 (3) | −0.012 (2) | 0.010 (2) | −0.006 (2) |
C13 | 0.052 (3) | 0.045 (3) | 0.062 (3) | 0.002 (2) | 0.008 (2) | −0.006 (2) |
C14 | 0.045 (3) | 0.043 (3) | 0.064 (3) | 0.010 (2) | 0.014 (2) | −0.009 (2) |
C15 | 0.064 (4) | 0.059 (3) | 0.069 (3) | −0.006 (3) | 0.032 (3) | 0.013 (3) |
C16 | 0.081 (4) | 0.033 (3) | 0.066 (3) | −0.004 (3) | 0.016 (3) | 0.012 (2) |
C17 | 0.031 (3) | 0.039 (3) | 0.031 (2) | 0.005 (2) | 0.007 (2) | 0.006 (2) |
C18 | 0.044 (3) | 0.044 (3) | 0.047 (3) | 0.007 (2) | 0.014 (2) | 0.001 (2) |
C19 | 0.054 (3) | 0.050 (3) | 0.055 (3) | 0.010 (3) | 0.022 (3) | −0.013 (2) |
C20 | 0.055 (3) | 0.051 (3) | 0.073 (3) | 0.004 (3) | 0.008 (3) | −0.022 (3) |
C21 | 0.044 (3) | 0.053 (3) | 0.069 (3) | −0.007 (3) | 0.013 (3) | −0.018 (3) |
C22 | 0.050 (3) | 0.044 (3) | 0.044 (3) | −0.001 (2) | 0.013 (2) | −0.016 (2) |
C23 | 0.026 (3) | 0.044 (3) | 0.040 (2) | −0.006 (2) | 0.012 (2) | −0.003 (2) |
C24 | 0.036 (3) | 0.033 (2) | 0.033 (2) | 0.003 (2) | −0.003 (2) | 0.002 (2) |
C25 | 0.038 (3) | 0.042 (3) | 0.063 (3) | −0.012 (2) | 0.010 (2) | −0.009 (2) |
C26 | 0.166 (7) | 0.318 (10) | 0.133 (5) | −0.179 (7) | 0.097 (5) | −0.175 (6) |
C27 | 0.164 (7) | 0.060 (4) | 0.260 (8) | −0.064 (5) | −0.062 (6) | 0.040 (5) |
C28 | 0.034 (3) | 0.119 (5) | 0.235 (7) | −0.019 (4) | 0.015 (4) | −0.100 (5) |
C29 | 0.054 (3) | 0.142 (5) | 0.038 (3) | 0.016 (3) | 0.007 (2) | 0.014 (3) |
C30 | 0.056 (3) | 0.036 (3) | 0.151 (4) | 0.015 (3) | 0.025 (3) | 0.022 (3) |
C31 | 0.050 (3) | 0.054 (3) | 0.093 (4) | −0.004 (3) | 0.019 (3) | 0.000 (3) |
C32 | 0.050 (3) | 0.084 (4) | 0.064 (3) | 0.006 (3) | 0.029 (3) | 0.002 (3) |
C33 | 0.110 (4) | 0.047 (3) | 0.062 (3) | 0.000 (3) | 0.010 (3) | 0.015 (3) |
C34 | 0.063 (4) | 0.092 (4) | 0.050 (3) | 0.003 (3) | −0.002 (3) | 0.009 (3) |
C35 | 0.096 (4) | 0.050 (3) | 0.033 (3) | −0.001 (3) | 0.007 (3) | 0.008 (2) |
C36 | 0.088 (4) | 0.050 (3) | 0.046 (3) | 0.001 (3) | 0.039 (3) | −0.007 (2) |
C37 | 0.059 (4) | 0.060 (3) | 0.083 (4) | −0.001 (3) | 0.034 (3) | −0.007 (3) |
C38 | 0.084 (4) | 0.052 (3) | 0.060 (3) | 0.001 (3) | 0.024 (3) | 0.001 (2) |
C39 | 0.098 (4) | 0.096 (4) | 0.071 (3) | −0.026 (4) | 0.031 (3) | −0.035 (3) |
C40 | 0.074 (4) | 0.084 (4) | 0.048 (3) | −0.009 (3) | 0.015 (3) | −0.003 (3) |
C41 | 0.080 (4) | 0.122 (5) | 0.033 (3) | 0.021 (4) | 0.004 (3) | 0.007 (3) |
C42 | 0.094 (5) | 0.096 (5) | 0.062 (4) | 0.019 (4) | 0.026 (3) | 0.022 (3) |
C43 | 0.079 (4) | 0.052 (3) | 0.097 (4) | −0.012 (3) | 0.009 (3) | −0.003 (3) |
C44 | 0.066 (4) | 0.068 (4) | 0.048 (3) | 0.022 (3) | 0.007 (3) | 0.010 (2) |
Li1—N1 | 2.003 (6) | C17—C18 | 1.396 (4) |
Li1—N6 | 2.119 (7) | C17—C22 | 1.399 (5) |
Li1—N5 | 2.137 (7) | C17—C23 | 1.446 (4) |
Li1—N2 | 2.328 (7) | C18—C19 | 1.388 (4) |
Li2—N3 | 2.013 (7) | C18—H18 | 0.9300 |
Li2—N7 | 2.143 (7) | C19—C20 | 1.364 (5) |
Li2—N8 | 2.137 (7) | C19—H19 | 0.9300 |
Li2—N4 | 2.220 (7) | C20—C21 | 1.377 (5) |
Si1—N1 | 1.647 (3) | C20—H20 | 0.9300 |
Si1—N2 | 1.764 (3) | C21—C22 | 1.376 (4) |
Si1—C14 | 1.874 (4) | C21—H21 | 0.9300 |
Si1—C13 | 1.888 (3) | C22—H22 | 0.9300 |
Si2—N3 | 1.649 (3) | C23—C24 | 1.359 (4) |
Si2—N4 | 1.766 (3) | C23—H23 | 0.9300 |
Si2—C29 | 1.876 (3) | C24—C25 | 1.553 (5) |
Si2—C30 | 1.876 (4) | C25—C26 | 1.443 (5) |
N1—C8 | 1.361 (4) | C25—C28 | 1.485 (5) |
N2—C15 | 1.467 (4) | C25—C27 | 1.532 (6) |
N2—C16 | 1.477 (4) | C26—H26A | 0.9600 |
N3—C24 | 1.383 (4) | C26—H26B | 0.9600 |
N4—C31 | 1.467 (4) | C26—H26C | 0.9600 |
N4—C32 | 1.480 (4) | C27—H27A | 0.9600 |
N5—C33 | 1.462 (4) | C27—H27B | 0.9600 |
N5—C35 | 1.467 (4) | C27—H27C | 0.9600 |
N5—C34 | 1.502 (4) | C28—H28A | 0.9600 |
N6—C37 | 1.461 (4) | C28—H28B | 0.9600 |
N6—C36 | 1.463 (4) | C28—H28C | 0.9600 |
N6—C38 | 1.473 (4) | C29—H29A | 0.9600 |
N7—C41 | 1.463 (5) | C29—H29B | 0.9600 |
N7—C40 | 1.472 (5) | C29—H29C | 0.9600 |
N7—C39 | 1.467 (5) | C30—H30A | 0.9600 |
N8—C43 | 1.452 (4) | C30—H30B | 0.9600 |
N8—C42 | 1.464 (4) | C30—H30C | 0.9600 |
N8—C44 | 1.477 (4) | C31—H31A | 0.9600 |
C1—C2 | 1.371 (5) | C31—H31B | 0.9600 |
C1—C6 | 1.386 (5) | C31—H31C | 0.9600 |
C1—C7 | 1.472 (5) | C32—H32A | 0.9600 |
C2—C3 | 1.374 (5) | C32—H32B | 0.9600 |
C2—H2 | 0.9300 | C32—H32C | 0.9600 |
C3—C4 | 1.363 (5) | C33—H33A | 0.9600 |
C3—H3 | 0.9300 | C33—H33B | 0.9600 |
C4—C5 | 1.372 (6) | C33—H33C | 0.9600 |
C4—H4 | 0.9300 | C34—H34A | 0.9600 |
C5—C6 | 1.372 (5) | C34—H34B | 0.9600 |
C5—H5 | 0.9300 | C34—H34C | 0.9600 |
C6—H6 | 0.9300 | C35—C36 | 1.532 (5) |
C7—C8 | 1.362 (4) | C35—H35A | 0.9700 |
C7—H7 | 0.9300 | C35—H35B | 0.9700 |
C8—C9 | 1.559 (5) | C36—H36A | 0.9700 |
C9—C11 | 1.525 (4) | C36—H36B | 0.9700 |
C9—C12 | 1.526 (4) | C37—H37A | 0.9600 |
C9—C10 | 1.529 (4) | C37—H37B | 0.9600 |
C10—H10A | 0.9600 | C37—H37C | 0.9600 |
C10—H10B | 0.9600 | C38—H38A | 0.9600 |
C10—H10C | 0.9600 | C38—H38B | 0.9600 |
C11—H11A | 0.9600 | C38—H38C | 0.9600 |
C11—H11B | 0.9600 | C39—H39A | 0.9600 |
C11—H11C | 0.9600 | C39—H39B | 0.9600 |
C12—H12A | 0.9600 | C39—H39C | 0.9600 |
C12—H12B | 0.9600 | C40—H40A | 0.9600 |
C12—H12C | 0.9600 | C40—H40B | 0.9600 |
C13—H13A | 0.9600 | C40—H40C | 0.9600 |
C13—H13B | 0.9600 | C41—C42 | 1.516 (5) |
C13—H13C | 0.9600 | C41—H41A | 0.9700 |
C14—H14A | 0.9600 | C41—H41B | 0.9700 |
C14—H14B | 0.9600 | C42—H42A | 0.9700 |
C14—H14C | 0.9600 | C42—H42B | 0.9700 |
C15—H15A | 0.9600 | C43—H43A | 0.9600 |
C15—H15B | 0.9600 | C43—H43B | 0.9600 |
C15—H15C | 0.9600 | C43—H43C | 0.9600 |
C16—H16A | 0.9600 | C44—H44A | 0.9600 |
C16—H16B | 0.9600 | C44—H44B | 0.9600 |
C16—H16C | 0.9600 | C44—H44C | 0.9600 |
N1—Li1—N6 | 124.0 (3) | C19—C18—C17 | 122.3 (4) |
N1—Li1—N5 | 138.0 (4) | C19—C18—H18 | 118.9 |
N6—Li1—N5 | 85.9 (3) | C17—C18—H18 | 118.9 |
N1—Li1—N2 | 75.0 (2) | C20—C19—C18 | 120.7 (4) |
N6—Li1—N2 | 132.9 (3) | C20—C19—H19 | 119.6 |
N5—Li1—N2 | 107.4 (3) | C18—C19—H19 | 119.6 |
N3—Li2—N7 | 136.9 (4) | C19—C20—C21 | 118.5 (4) |
N3—Li2—N8 | 120.4 (4) | C19—C20—H20 | 120.8 |
N7—Li2—N8 | 84.9 (3) | C21—C20—H20 | 120.8 |
N3—Li2—N4 | 77.5 (2) | C22—C21—C20 | 121.0 (4) |
N7—Li2—N4 | 114.2 (3) | C22—C21—H21 | 119.5 |
N8—Li2—N4 | 130.1 (3) | C20—C21—H21 | 119.5 |
N1—Si1—N2 | 101.80 (15) | C21—C22—C17 | 122.2 (4) |
N1—Si1—C14 | 119.66 (16) | C21—C22—H22 | 118.9 |
N2—Si1—C14 | 103.43 (16) | C17—C22—H22 | 118.9 |
N1—Si1—C13 | 115.28 (15) | C24—C23—C17 | 132.1 (4) |
N2—Si1—C13 | 110.19 (16) | C24—C23—H23 | 113.9 |
C14—Si1—C13 | 105.59 (16) | C17—C23—H23 | 113.9 |
N3—Si2—N4 | 101.99 (15) | C23—C24—N3 | 125.8 (4) |
N3—Si2—C29 | 114.94 (16) | C23—C24—C25 | 117.6 (4) |
N4—Si2—C29 | 111.60 (17) | N3—C24—C25 | 116.5 (3) |
N3—Si2—C30 | 119.26 (17) | C26—C25—C28 | 109.3 (4) |
N4—Si2—C30 | 104.52 (18) | C26—C25—C27 | 107.2 (4) |
C29—Si2—C30 | 104.14 (19) | C28—C25—C27 | 104.7 (4) |
C8—N1—Si1 | 142.4 (2) | C26—C25—C24 | 111.9 (4) |
C8—N1—Li1 | 121.2 (3) | C28—C25—C24 | 116.1 (4) |
Si1—N1—Li1 | 94.3 (2) | C27—C25—C24 | 107.1 (3) |
C15—N2—C16 | 107.8 (3) | C25—C26—H26A | 109.5 |
C15—N2—Si1 | 116.9 (2) | C25—C26—H26B | 109.5 |
C16—N2—Si1 | 119.7 (3) | H26A—C26—H26B | 109.5 |
C15—N2—Li1 | 92.8 (3) | C25—C26—H26C | 109.5 |
C16—N2—Li1 | 136.1 (3) | H26A—C26—H26C | 109.5 |
Si1—N2—Li1 | 80.77 (19) | H26B—C26—H26C | 109.5 |
C24—N3—Si2 | 134.2 (3) | C25—C27—H27A | 109.5 |
C24—N3—Li2 | 131.4 (3) | C25—C27—H27B | 109.5 |
Si2—N3—Li2 | 94.3 (2) | H27A—C27—H27B | 109.5 |
C31—N4—C32 | 108.6 (3) | C25—C27—H27C | 109.5 |
C31—N4—Si2 | 116.0 (2) | H27A—C27—H27C | 109.5 |
C32—N4—Si2 | 118.4 (3) | H27B—C27—H27C | 109.5 |
C31—N4—Li2 | 103.2 (3) | C25—C28—H28A | 109.5 |
C32—N4—Li2 | 124.3 (3) | C25—C28—H28B | 109.5 |
Si2—N4—Li2 | 84.3 (2) | H28A—C28—H28B | 109.5 |
C33—N5—C35 | 111.2 (3) | C25—C28—H28C | 109.5 |
C33—N5—C34 | 108.6 (3) | H28A—C28—H28C | 109.5 |
C35—N5—C34 | 107.2 (3) | H28B—C28—H28C | 109.5 |
C33—N5—Li1 | 105.6 (3) | Si2—C29—H29A | 109.5 |
C35—N5—Li1 | 104.3 (3) | Si2—C29—H29B | 109.5 |
C34—N5—Li1 | 119.9 (3) | H29A—C29—H29B | 109.5 |
C37—N6—C36 | 108.9 (3) | Si2—C29—H29C | 109.5 |
C37—N6—C38 | 108.8 (3) | H29A—C29—H29C | 109.5 |
C36—N6—C38 | 110.5 (3) | H29B—C29—H29C | 109.5 |
C37—N6—Li1 | 119.3 (3) | Si2—C30—H30A | 109.5 |
C36—N6—Li1 | 103.8 (3) | Si2—C30—H30B | 109.5 |
C38—N6—Li1 | 105.3 (3) | H30A—C30—H30B | 109.5 |
C41—N7—C40 | 111.2 (4) | Si2—C30—H30C | 109.5 |
C41—N7—C39 | 109.5 (4) | H30A—C30—H30C | 109.5 |
C40—N7—C39 | 107.4 (3) | H30B—C30—H30C | 109.5 |
C41—N7—Li2 | 102.8 (3) | N4—C31—H31A | 109.5 |
C40—N7—Li2 | 105.2 (3) | N4—C31—H31B | 109.5 |
C39—N7—Li2 | 120.7 (3) | H31A—C31—H31B | 109.5 |
C43—N8—C42 | 109.5 (3) | N4—C31—H31C | 109.5 |
C43—N8—C44 | 108.8 (3) | H31A—C31—H31C | 109.5 |
C42—N8—C44 | 110.4 (3) | H31B—C31—H31C | 109.5 |
C43—N8—Li2 | 121.3 (3) | N4—C32—H32A | 109.5 |
C42—N8—Li2 | 106.1 (3) | N4—C32—H32B | 109.5 |
C44—N8—Li2 | 100.2 (3) | H32A—C32—H32B | 109.5 |
C2—C1—C6 | 117.5 (4) | N4—C32—H32C | 109.5 |
C2—C1—C7 | 123.7 (4) | H32A—C32—H32C | 109.5 |
C6—C1—C7 | 118.8 (4) | H32B—C32—H32C | 109.5 |
C3—C2—C1 | 121.1 (4) | N5—C33—H33A | 109.5 |
C3—C2—H2 | 119.4 | N5—C33—H33B | 109.5 |
C1—C2—H2 | 119.4 | H33A—C33—H33B | 109.5 |
C4—C3—C2 | 121.5 (4) | N5—C33—H33C | 109.5 |
C4—C3—H3 | 119.2 | H33A—C33—H33C | 109.5 |
C2—C3—H3 | 119.2 | H33B—C33—H33C | 109.5 |
C3—C4—C5 | 117.6 (4) | N5—C34—H34A | 109.5 |
C3—C4—H4 | 121.2 | N5—C34—H34B | 109.5 |
C5—C4—H4 | 121.2 | H34A—C34—H34B | 109.5 |
C6—C5—C4 | 121.5 (4) | N5—C34—H34C | 109.5 |
C6—C5—H5 | 119.3 | H34A—C34—H34C | 109.5 |
C4—C5—H5 | 119.3 | H34B—C34—H34C | 109.5 |
C5—C6—C1 | 120.7 (4) | N5—C35—C36 | 110.8 (3) |
C5—C6—H6 | 119.7 | N5—C35—H35A | 109.5 |
C1—C6—H6 | 119.7 | C36—C35—H35A | 109.5 |
C8—C7—C1 | 128.8 (4) | N5—C35—H35B | 109.5 |
C8—C7—H7 | 115.6 | C36—C35—H35B | 109.5 |
C1—C7—H7 | 115.6 | H35A—C35—H35B | 108.1 |
C7—C8—N1 | 124.5 (4) | N6—C36—C35 | 111.6 (3) |
C7—C8—C9 | 118.0 (3) | N6—C36—H36A | 109.3 |
N1—C8—C9 | 117.4 (3) | C35—C36—H36A | 109.3 |
C11—C9—C12 | 109.7 (3) | N6—C36—H36B | 109.3 |
C11—C9—C10 | 107.1 (3) | C35—C36—H36B | 109.3 |
C12—C9—C10 | 107.0 (3) | H36A—C36—H36B | 108.0 |
C11—C9—C8 | 107.5 (3) | N6—C37—H37A | 109.5 |
C12—C9—C8 | 110.4 (3) | N6—C37—H37B | 109.5 |
C10—C9—C8 | 115.0 (3) | H37A—C37—H37B | 109.5 |
C9—C10—H10A | 109.5 | N6—C37—H37C | 109.5 |
C9—C10—H10B | 109.5 | H37A—C37—H37C | 109.5 |
H10A—C10—H10B | 109.5 | H37B—C37—H37C | 109.5 |
C9—C10—H10C | 109.5 | N6—C38—H38A | 109.5 |
H10A—C10—H10C | 109.5 | N6—C38—H38B | 109.5 |
H10B—C10—H10C | 109.5 | H38A—C38—H38B | 109.5 |
C9—C11—H11A | 109.5 | N6—C38—H38C | 109.5 |
C9—C11—H11B | 109.5 | H38A—C38—H38C | 109.5 |
H11A—C11—H11B | 109.5 | H38B—C38—H38C | 109.5 |
C9—C11—H11C | 109.5 | N7—C39—H39A | 109.5 |
H11A—C11—H11C | 109.5 | N7—C39—H39B | 109.5 |
H11B—C11—H11C | 109.5 | H39A—C39—H39B | 109.5 |
C9—C12—H12A | 109.5 | N7—C39—H39C | 109.5 |
C9—C12—H12B | 109.5 | H39A—C39—H39C | 109.5 |
H12A—C12—H12B | 109.5 | H39B—C39—H39C | 109.5 |
C9—C12—H12C | 109.5 | N7—C40—H40A | 109.5 |
H12A—C12—H12C | 109.5 | N7—C40—H40B | 109.5 |
H12B—C12—H12C | 109.5 | H40A—C40—H40B | 109.5 |
Si1—C13—H13A | 109.5 | N7—C40—H40C | 109.5 |
Si1—C13—H13B | 109.5 | H40A—C40—H40C | 109.5 |
H13A—C13—H13B | 109.5 | H40B—C40—H40C | 109.5 |
Si1—C13—H13C | 109.5 | N7—C41—C42 | 111.9 (4) |
H13A—C13—H13C | 109.5 | N7—C41—H41A | 109.2 |
H13B—C13—H13C | 109.5 | C42—C41—H41A | 109.2 |
Si1—C14—H14A | 109.5 | N7—C41—H41B | 109.2 |
Si1—C14—H14B | 109.5 | C42—C41—H41B | 109.2 |
H14A—C14—H14B | 109.5 | H41A—C41—H41B | 107.9 |
Si1—C14—H14C | 109.5 | N8—C42—C41 | 111.7 (4) |
H14A—C14—H14C | 109.5 | N8—C42—H42A | 109.3 |
H14B—C14—H14C | 109.5 | C41—C42—H42A | 109.3 |
N2—C15—H15A | 109.5 | N8—C42—H42B | 109.3 |
N2—C15—H15B | 109.5 | C41—C42—H42B | 109.3 |
H15A—C15—H15B | 109.5 | H42A—C42—H42B | 107.9 |
N2—C15—H15C | 109.5 | N8—C43—H43A | 109.5 |
H15A—C15—H15C | 109.5 | N8—C43—H43B | 109.5 |
H15B—C15—H15C | 109.5 | H43A—C43—H43B | 109.5 |
N2—C16—H16A | 109.5 | N8—C43—H43C | 109.5 |
N2—C16—H16B | 109.5 | H43A—C43—H43C | 109.5 |
H16A—C16—H16B | 109.5 | H43B—C43—H43C | 109.5 |
N2—C16—H16C | 109.5 | N8—C44—H44A | 109.5 |
H16A—C16—H16C | 109.5 | N8—C44—H44B | 109.5 |
H16B—C16—H16C | 109.5 | H44A—C44—H44B | 109.5 |
C18—C17—C22 | 115.3 (4) | N8—C44—H44C | 109.5 |
C18—C17—C23 | 119.4 (4) | H44A—C44—H44C | 109.5 |
C22—C17—C23 | 125.2 (4) | H44B—C44—H44C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Li(C16H27N2Si)(C6H16N2)] |
Mr | 398.63 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 178 |
a, b, c (Å) | 14.819 (3), 9.4142 (16), 18.635 (3) |
β (°) | 97.674 (3) |
V (Å3) | 2576.4 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.40 × 0.30 × 0.30 |
Data collection | |
Diffractometer | Bruker CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.960, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10666, 8386, 4772 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.066, 0.83 |
No. of reflections | 8386 |
No. of parameters | 527 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.25 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.05 (11) |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
Li2—N3 | 2.013 (7) | Si2—C29 | 1.876 (3) |
Li2—N7 | 2.143 (7) | Si2—C30 | 1.876 (4) |
Li2—N8 | 2.137 (7) | N3—C24 | 1.383 (4) |
Li2—N4 | 2.220 (7) | N4—C31 | 1.467 (4) |
Si2—N3 | 1.649 (3) | N4—C32 | 1.480 (4) |
Si2—N4 | 1.766 (3) | ||
N3—Li2—N7 | 136.9 (4) | C24—N3—Li2 | 131.4 (3) |
N3—Li2—N8 | 120.4 (4) | Si2—N3—Li2 | 94.3 (2) |
N7—Li2—N8 | 84.9 (3) | C31—N4—C32 | 108.6 (3) |
N3—Li2—N4 | 77.5 (2) | C31—N4—Si2 | 116.0 (2) |
N7—Li2—N4 | 114.2 (3) | C32—N4—Si2 | 118.4 (3) |
N8—Li2—N4 | 130.1 (3) | C31—N4—Li2 | 103.2 (3) |
N3—Si2—N4 | 101.99 (15) | C32—N4—Li2 | 124.3 (3) |
N3—Si2—C29 | 114.94 (16) | Si2—N4—Li2 | 84.3 (2) |
N4—Si2—C29 | 111.60 (17) | C24—C23—C17 | 132.1 (4) |
N3—Si2—C30 | 119.26 (17) | C23—C24—N3 | 125.8 (4) |
N4—Si2—C30 | 104.52 (18) | C23—C24—C25 | 117.6 (4) |
C29—Si2—C30 | 104.14 (19) | N3—C24—C25 | 116.5 (3) |
C24—N3—Si2 | 134.2 (3) |
There is much current interest in the structures of organolithium compounds. We describe below an organolithium compound that has an unprecedented structure with several unusual features and possesses important potential for synthesis of other novel organometallic compounds.
The novel title compound, (I), containing the N—Si—N—Li fragment, has been characterized by single-crystal X-ray diffraction analysis. The geometric parameters of the moiety of (I) are listed in Table 1 and the molecular structure is illustrated in Fig 1. This compound shows several interesting features, as follows: (i) there is a four-membered ring where two N atoms were bonded to the Li atom; the ring contains a planar N atom (N3 sum of angles 359.9°), a four-coordinate Li center, and a four-coordinate N center, N4. (ii) The four-membered ring adopts a folded conformation. The angle between the Li2/N3/Si2 and Li2/N4/Si2 planes is 14.6°. The angle between the N3/Si2/N4 and N3/Li2/N4 planes is 15.0°. (iii) As a consequence of the coordination of N4 to Li, the Si2—N4 bond length [1.766 (3) Å] is longer than the N3—Si2 bond length [1.649 (3) Å]; in the R3Si–NR'2 species, the Si—-N bond lengths fall in the range 1.710–1.721 Å (Lukevics et al., 1985). (iv) The N3—C24 bond length [1.383 (4) Å] is much shorter than the common N—Csp3 bond length, which usually lies in the range 1.45–1.48 Å, and this can be attributed to delocalization of the negative charge either by π–π bonding or more likely to negative conjugation leading to some double-bond character in the N3—C24 bond (Brinkman et al., 1994). It is noteworthy that much novel species should be formed by use of this title compound.