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The crystal structure of the title compound, [Li(C16H27N2Si)(C6H16N2)], contains the N—Si—N—Li four-membered heterocycle. The heterocycle contains a planar three-coord­inated N-atom centre, a four-coordinated N-atom centre, a four-coordinate Li-atom centre and a four-coordinated Si-atom centre, and adopts a folded conform­ation. There are two molecules in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010353/ac6040sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010353/ac6040Isup2.hkl
Contains datablock I

CCDC reference: 214781

Key indicators

  • Single-crystal X-ray study
  • T = 178 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.058
  • wR factor = 0.066
  • Data-to-parameter ratio = 15.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
PLAT_213 Alert B Atom C26 has ADP max/min Ratio ........... 4.60 prolate
Yellow Alert Alert Level C:
PLAT_213 Alert C Atom C27 has ADP max/min Ratio ........... 3.40 prolate PLAT_213 Alert C Atom C28 has ADP max/min Ratio ........... 3.20 prolate General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 8386 Count of symmetry unique reflns 4840 Completeness (_total/calc) 173.26% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3546 Fraction of Friedel pairs measured 0.733 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

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 ππ 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.

Experimental top

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.

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by small spheres of arbitrary radii.
[Figure 2] Fig. 2. A packing diagram of the title molecule, viewed along the a axis. For clarity, all H atoms have been omitted.
[(1-tert-Butyl-2-phenylvinylamino)(dimethylamino)dimethylsilyl-κ2N,N'] (N,N,N',N'-tetramethylenediamine-κ2N,N')lithium(I) top
Crystal data top
[Li(C16H27N2Si)(C6H16N2)]F(000) = 880
Mr = 398.63Dx = 1.028 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 14.819 (3) ÅCell parameters from 1711 reflections
b = 9.4142 (16) Åθ = 2.4–18.0°
c = 18.635 (3) ŵ = 0.10 mm1
β = 97.674 (3)°T = 178 K
V = 2576.4 (8) Å3Block, colorless
Z = 40.40 × 0.30 × 0.30 mm
Data collection top
Bruker CCD area-detector
diffractometer
8386 independent reflections
Radiation source: oil sealed4772 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1716
Tmin = 0.960, Tmax = 0.969k = 1111
10666 measured reflectionsl = 1822
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-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 reflectionsΔρmax = 0.34 e Å3
527 parametersΔρmin = 0.25 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (11)
Crystal data top
[Li(C16H27N2Si)(C6H16N2)]V = 2576.4 (8) Å3
Mr = 398.63Z = 4
Monoclinic, P21Mo Kα radiation
a = 14.819 (3) ŵ = 0.10 mm1
b = 9.4142 (16) ÅT = 178 K
c = 18.635 (3) Å0.40 × 0.30 × 0.30 mm
β = 97.674 (3)°
Data collection top
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 = 0.969Rint = 0.043
10666 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.066Δρmax = 0.34 e Å3
S = 0.83Δρmin = 0.25 e Å3
8386 reflectionsAbsolute structure: Flack (1983)
527 parametersAbsolute structure parameter: 0.05 (11)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken

into account individually in the estimation of e.s.d.'s in distances, angles

and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Li10.2004 (4)0.2342 (7)0.2651 (3)0.0437 (18)
Li20.6702 (5)0.5323 (7)0.2263 (4)0.0463 (19)
Si10.16518 (8)0.38917 (12)0.37918 (5)0.0365 (3)
Si20.61781 (8)0.69132 (11)0.10769 (6)0.0400 (3)
N10.18673 (19)0.2189 (3)0.37029 (13)0.0302 (8)
N20.2199 (2)0.4647 (3)0.30983 (16)0.0404 (9)
N30.7173 (2)0.6236 (3)0.14095 (14)0.0322 (8)
N40.5430 (2)0.6025 (3)0.15889 (15)0.0404 (9)
N50.1145 (2)0.2461 (3)0.16363 (15)0.0458 (9)
N60.2835 (2)0.0980 (3)0.21143 (16)0.0436 (9)
N70.6742 (3)0.5756 (4)0.33954 (17)0.0540 (10)
N80.7140 (2)0.3240 (3)0.26068 (17)0.0463 (9)
C10.3473 (3)0.0256 (4)0.42463 (19)0.0379 (11)
C20.3865 (3)0.1577 (4)0.43098 (18)0.0407 (11)
H20.35000.23710.43430.049*
C30.4789 (3)0.1748 (5)0.4325 (2)0.0545 (12)
H30.50350.26570.43650.065*
C40.5352 (3)0.0614 (5)0.4284 (2)0.0667 (15)
H40.59740.07370.42800.080*
C50.4968 (3)0.0715 (5)0.4247 (2)0.0699 (15)
H50.53410.15070.42350.084*
C60.4047 (3)0.0901 (5)0.4228 (2)0.0609 (13)
H60.38050.18140.42020.073*
C70.2490 (3)0.0004 (4)0.42309 (16)0.0346 (11)
H70.23300.08900.43850.042*
C80.1783 (3)0.0902 (4)0.40210 (17)0.0297 (10)
C90.0803 (3)0.0392 (4)0.4110 (2)0.0399 (11)
C100.0728 (3)0.1177 (4)0.43058 (19)0.0603 (13)
H10A0.10540.13440.47790.090*
H10B0.09820.17500.39570.090*
H10C0.00980.14210.43050.090*
C110.0487 (2)0.1253 (4)0.47231 (18)0.0538 (12)
H11A0.08700.10460.51680.081*
H11B0.01310.10060.47700.081*
H11C0.05220.22470.46170.081*
C120.0158 (2)0.0639 (4)0.34123 (18)0.0516 (12)
H12A0.04510.03950.34880.077*
H12B0.03400.00550.30340.077*
H12C0.01790.16200.32760.077*
C130.2112 (2)0.4694 (4)0.46952 (16)0.0526 (12)
H13A0.17950.43010.50660.079*
H13B0.20270.57040.46760.079*
H13C0.27500.44840.48030.079*
C140.0453 (2)0.4555 (4)0.35867 (18)0.0500 (12)
H14A0.02210.43420.30920.075*
H14B0.04420.55630.36610.075*
H14C0.00800.40980.39020.075*
C150.3195 (3)0.4543 (4)0.31790 (19)0.0618 (14)
H15A0.34020.47230.27210.093*
H15B0.33790.36070.33420.093*
H15C0.34560.52310.35270.093*
C160.1942 (3)0.6088 (4)0.28296 (19)0.0595 (14)
H16A0.21810.67780.31840.089*
H16B0.12910.61650.27440.089*
H16C0.21880.62560.23860.089*
C170.8072 (3)0.4138 (4)0.04034 (18)0.0330 (10)
C180.8606 (3)0.3436 (4)0.00472 (19)0.0440 (12)
H180.91790.37990.00960.053*
C190.8313 (3)0.2214 (4)0.0426 (2)0.0519 (12)
H190.86840.17890.07290.062*
C200.7486 (3)0.1631 (4)0.0358 (2)0.0598 (13)
H200.72940.08010.06030.072*
C210.6940 (3)0.2298 (4)0.0082 (2)0.0549 (13)
H210.63690.19260.01240.066*
C220.7229 (3)0.3508 (4)0.04592 (19)0.0456 (12)
H220.68510.39190.07610.055*
C230.8421 (2)0.5402 (4)0.07857 (18)0.0359 (10)
H230.90160.56240.07220.043*
C240.8042 (3)0.6326 (4)0.12200 (19)0.0347 (10)
C250.8638 (3)0.7587 (4)0.1545 (2)0.0473 (12)
C260.8430 (4)0.7981 (7)0.2253 (3)0.199 (4)
H26A0.86280.72430.25930.298*
H26B0.77840.81130.22350.298*
H26C0.87380.88500.24030.298*
C270.8404 (4)0.8865 (5)0.1046 (3)0.170 (3)
H27A0.77880.87820.08140.255*
H27B0.88090.88890.06840.255*
H27C0.84700.97240.13250.255*
C280.9637 (3)0.7409 (5)0.1573 (3)0.129 (2)
H28A0.99410.82440.17800.194*
H28B0.97860.72700.10920.194*
H28C0.98320.65980.18660.194*
C290.5846 (3)0.6635 (5)0.00799 (17)0.0780 (16)
H29A0.62840.70840.01810.117*
H29B0.52560.70420.00660.117*
H29C0.58270.56360.00240.117*
C300.5955 (3)0.8849 (4)0.1215 (2)0.0798 (15)
H30A0.61260.90890.17160.120*
H30B0.53190.90430.10800.120*
H30C0.63060.94060.09210.120*
C310.5038 (3)0.4692 (4)0.1281 (2)0.0647 (14)
H31A0.45530.49000.09010.097*
H31B0.48050.41520.16530.097*
H31C0.55010.41540.10880.097*
C320.4702 (3)0.6857 (4)0.18646 (19)0.0642 (13)
H32A0.42700.71670.14650.096*
H32B0.49640.76690.21260.096*
H32C0.44000.62750.21820.096*
C330.1314 (3)0.3859 (4)0.13395 (19)0.0730 (15)
H33A0.19590.40170.13740.109*
H33B0.10460.45790.16090.109*
H33C0.10500.39000.08410.109*
C340.0135 (3)0.2265 (5)0.16079 (18)0.0692 (14)
H34A0.01450.22770.11130.104*
H34B0.01100.30210.18690.104*
H34C0.00150.13710.18240.104*
C350.1476 (3)0.1322 (4)0.12019 (19)0.0597 (14)
H35A0.12880.15100.06920.072*
H35B0.12090.04250.13210.072*
C360.2516 (3)0.1214 (4)0.1346 (2)0.0586 (13)
H36A0.27170.04350.10660.070*
H36B0.27810.20820.11890.070*
C370.3823 (3)0.1157 (4)0.22378 (19)0.0651 (14)
H37A0.41030.04590.19640.098*
H37B0.40370.10380.27440.098*
H37C0.39790.20910.20870.098*
C380.2609 (3)0.0468 (4)0.23303 (19)0.0637 (14)
H38A0.19610.05580.23090.096*
H38B0.28930.06470.28160.096*
H38C0.28270.11420.20070.096*
C390.7040 (3)0.7147 (5)0.3694 (2)0.0867 (17)
H39A0.69820.71720.42010.130*
H39B0.66670.78770.34470.130*
H39C0.76640.73010.36290.130*
C400.5804 (3)0.5531 (4)0.35499 (19)0.0681 (14)
H40A0.55510.47100.32910.102*
H40B0.54420.63500.33990.102*
H40C0.58080.53850.40600.102*
C410.7354 (3)0.4653 (6)0.3731 (2)0.0784 (17)
H41A0.73020.46050.42440.094*
H41B0.79770.49040.36810.094*
C420.7136 (3)0.3209 (5)0.3392 (2)0.0822 (17)
H42A0.75820.25230.36050.099*
H42B0.65420.29030.34960.099*
C430.6686 (3)0.1982 (4)0.2284 (2)0.0762 (15)
H43A0.66890.20030.17690.114*
H43B0.60690.19610.23890.114*
H43C0.70010.11490.24810.114*
C440.8084 (3)0.3267 (4)0.24340 (19)0.0610 (14)
H44A0.84020.24370.26320.092*
H44B0.83870.41020.26400.092*
H44C0.80760.32780.19180.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Li10.048 (5)0.037 (4)0.050 (4)0.004 (4)0.016 (4)0.004 (3)
Li20.042 (5)0.040 (4)0.055 (5)0.001 (4)0.001 (4)0.006 (4)
Si10.0368 (7)0.0327 (7)0.0406 (7)0.0008 (6)0.0073 (6)0.0030 (6)
Si20.0365 (8)0.0409 (8)0.0433 (7)0.0014 (6)0.0085 (6)0.0065 (6)
N10.036 (2)0.031 (2)0.0262 (18)0.0012 (17)0.0114 (15)0.0031 (15)
N20.038 (2)0.035 (2)0.051 (2)0.0037 (18)0.0133 (19)0.0106 (17)
N30.025 (2)0.0361 (19)0.037 (2)0.0020 (16)0.0097 (17)0.0002 (16)
N40.034 (2)0.042 (2)0.048 (2)0.0025 (18)0.0156 (18)0.0018 (18)
N50.065 (3)0.039 (2)0.035 (2)0.001 (2)0.009 (2)0.0025 (18)
N60.053 (3)0.045 (2)0.037 (2)0.001 (2)0.0201 (19)0.0009 (18)
N70.057 (3)0.068 (3)0.039 (2)0.008 (2)0.014 (2)0.006 (2)
N80.047 (3)0.045 (2)0.049 (2)0.002 (2)0.012 (2)0.0019 (18)
C10.043 (3)0.035 (3)0.037 (3)0.006 (2)0.010 (2)0.001 (2)
C20.038 (3)0.044 (3)0.042 (3)0.013 (2)0.009 (2)0.004 (2)
C30.048 (3)0.054 (3)0.060 (3)0.001 (3)0.003 (3)0.005 (3)
C40.046 (3)0.081 (4)0.073 (4)0.015 (3)0.011 (3)0.019 (3)
C50.053 (4)0.066 (4)0.093 (4)0.033 (3)0.020 (3)0.010 (3)
C60.062 (4)0.049 (3)0.072 (3)0.011 (3)0.012 (3)0.006 (3)
C70.053 (3)0.025 (2)0.029 (2)0.001 (2)0.012 (2)0.0088 (18)
C80.043 (3)0.028 (2)0.020 (2)0.005 (2)0.012 (2)0.0034 (18)
C90.045 (3)0.030 (2)0.048 (3)0.005 (2)0.017 (2)0.001 (2)
C100.071 (3)0.039 (3)0.079 (3)0.013 (3)0.037 (3)0.006 (3)
C110.047 (3)0.057 (3)0.062 (3)0.004 (2)0.023 (2)0.003 (2)
C120.041 (3)0.062 (3)0.052 (3)0.012 (2)0.010 (2)0.006 (2)
C130.052 (3)0.045 (3)0.062 (3)0.002 (2)0.008 (2)0.006 (2)
C140.045 (3)0.043 (3)0.064 (3)0.010 (2)0.014 (2)0.009 (2)
C150.064 (4)0.059 (3)0.069 (3)0.006 (3)0.032 (3)0.013 (3)
C160.081 (4)0.033 (3)0.066 (3)0.004 (3)0.016 (3)0.012 (2)
C170.031 (3)0.039 (3)0.031 (2)0.005 (2)0.007 (2)0.006 (2)
C180.044 (3)0.044 (3)0.047 (3)0.007 (2)0.014 (2)0.001 (2)
C190.054 (3)0.050 (3)0.055 (3)0.010 (3)0.022 (3)0.013 (2)
C200.055 (3)0.051 (3)0.073 (3)0.004 (3)0.008 (3)0.022 (3)
C210.044 (3)0.053 (3)0.069 (3)0.007 (3)0.013 (3)0.018 (3)
C220.050 (3)0.044 (3)0.044 (3)0.001 (2)0.013 (2)0.016 (2)
C230.026 (3)0.044 (3)0.040 (2)0.006 (2)0.012 (2)0.003 (2)
C240.036 (3)0.033 (2)0.033 (2)0.003 (2)0.003 (2)0.002 (2)
C250.038 (3)0.042 (3)0.063 (3)0.012 (2)0.010 (2)0.009 (2)
C260.166 (7)0.318 (10)0.133 (5)0.179 (7)0.097 (5)0.175 (6)
C270.164 (7)0.060 (4)0.260 (8)0.064 (5)0.062 (6)0.040 (5)
C280.034 (3)0.119 (5)0.235 (7)0.019 (4)0.015 (4)0.100 (5)
C290.054 (3)0.142 (5)0.038 (3)0.016 (3)0.007 (2)0.014 (3)
C300.056 (3)0.036 (3)0.151 (4)0.015 (3)0.025 (3)0.022 (3)
C310.050 (3)0.054 (3)0.093 (4)0.004 (3)0.019 (3)0.000 (3)
C320.050 (3)0.084 (4)0.064 (3)0.006 (3)0.029 (3)0.002 (3)
C330.110 (4)0.047 (3)0.062 (3)0.000 (3)0.010 (3)0.015 (3)
C340.063 (4)0.092 (4)0.050 (3)0.003 (3)0.002 (3)0.009 (3)
C350.096 (4)0.050 (3)0.033 (3)0.001 (3)0.007 (3)0.008 (2)
C360.088 (4)0.050 (3)0.046 (3)0.001 (3)0.039 (3)0.007 (2)
C370.059 (4)0.060 (3)0.083 (4)0.001 (3)0.034 (3)0.007 (3)
C380.084 (4)0.052 (3)0.060 (3)0.001 (3)0.024 (3)0.001 (2)
C390.098 (4)0.096 (4)0.071 (3)0.026 (4)0.031 (3)0.035 (3)
C400.074 (4)0.084 (4)0.048 (3)0.009 (3)0.015 (3)0.003 (3)
C410.080 (4)0.122 (5)0.033 (3)0.021 (4)0.004 (3)0.007 (3)
C420.094 (5)0.096 (5)0.062 (4)0.019 (4)0.026 (3)0.022 (3)
C430.079 (4)0.052 (3)0.097 (4)0.012 (3)0.009 (3)0.003 (3)
C440.066 (4)0.068 (4)0.048 (3)0.022 (3)0.007 (3)0.010 (2)
Geometric parameters (Å, º) top
Li1—N12.003 (6)C17—C181.396 (4)
Li1—N62.119 (7)C17—C221.399 (5)
Li1—N52.137 (7)C17—C231.446 (4)
Li1—N22.328 (7)C18—C191.388 (4)
Li2—N32.013 (7)C18—H180.9300
Li2—N72.143 (7)C19—C201.364 (5)
Li2—N82.137 (7)C19—H190.9300
Li2—N42.220 (7)C20—C211.377 (5)
Si1—N11.647 (3)C20—H200.9300
Si1—N21.764 (3)C21—C221.376 (4)
Si1—C141.874 (4)C21—H210.9300
Si1—C131.888 (3)C22—H220.9300
Si2—N31.649 (3)C23—C241.359 (4)
Si2—N41.766 (3)C23—H230.9300
Si2—C291.876 (3)C24—C251.553 (5)
Si2—C301.876 (4)C25—C261.443 (5)
N1—C81.361 (4)C25—C281.485 (5)
N2—C151.467 (4)C25—C271.532 (6)
N2—C161.477 (4)C26—H26A0.9600
N3—C241.383 (4)C26—H26B0.9600
N4—C311.467 (4)C26—H26C0.9600
N4—C321.480 (4)C27—H27A0.9600
N5—C331.462 (4)C27—H27B0.9600
N5—C351.467 (4)C27—H27C0.9600
N5—C341.502 (4)C28—H28A0.9600
N6—C371.461 (4)C28—H28B0.9600
N6—C361.463 (4)C28—H28C0.9600
N6—C381.473 (4)C29—H29A0.9600
N7—C411.463 (5)C29—H29B0.9600
N7—C401.472 (5)C29—H29C0.9600
N7—C391.467 (5)C30—H30A0.9600
N8—C431.452 (4)C30—H30B0.9600
N8—C421.464 (4)C30—H30C0.9600
N8—C441.477 (4)C31—H31A0.9600
C1—C21.371 (5)C31—H31B0.9600
C1—C61.386 (5)C31—H31C0.9600
C1—C71.472 (5)C32—H32A0.9600
C2—C31.374 (5)C32—H32B0.9600
C2—H20.9300C32—H32C0.9600
C3—C41.363 (5)C33—H33A0.9600
C3—H30.9300C33—H33B0.9600
C4—C51.372 (6)C33—H33C0.9600
C4—H40.9300C34—H34A0.9600
C5—C61.372 (5)C34—H34B0.9600
C5—H50.9300C34—H34C0.9600
C6—H60.9300C35—C361.532 (5)
C7—C81.362 (4)C35—H35A0.9700
C7—H70.9300C35—H35B0.9700
C8—C91.559 (5)C36—H36A0.9700
C9—C111.525 (4)C36—H36B0.9700
C9—C121.526 (4)C37—H37A0.9600
C9—C101.529 (4)C37—H37B0.9600
C10—H10A0.9600C37—H37C0.9600
C10—H10B0.9600C38—H38A0.9600
C10—H10C0.9600C38—H38B0.9600
C11—H11A0.9600C38—H38C0.9600
C11—H11B0.9600C39—H39A0.9600
C11—H11C0.9600C39—H39B0.9600
C12—H12A0.9600C39—H39C0.9600
C12—H12B0.9600C40—H40A0.9600
C12—H12C0.9600C40—H40B0.9600
C13—H13A0.9600C40—H40C0.9600
C13—H13B0.9600C41—C421.516 (5)
C13—H13C0.9600C41—H41A0.9700
C14—H14A0.9600C41—H41B0.9700
C14—H14B0.9600C42—H42A0.9700
C14—H14C0.9600C42—H42B0.9700
C15—H15A0.9600C43—H43A0.9600
C15—H15B0.9600C43—H43B0.9600
C15—H15C0.9600C43—H43C0.9600
C16—H16A0.9600C44—H44A0.9600
C16—H16B0.9600C44—H44B0.9600
C16—H16C0.9600C44—H44C0.9600
N1—Li1—N6124.0 (3)C19—C18—C17122.3 (4)
N1—Li1—N5138.0 (4)C19—C18—H18118.9
N6—Li1—N585.9 (3)C17—C18—H18118.9
N1—Li1—N275.0 (2)C20—C19—C18120.7 (4)
N6—Li1—N2132.9 (3)C20—C19—H19119.6
N5—Li1—N2107.4 (3)C18—C19—H19119.6
N3—Li2—N7136.9 (4)C19—C20—C21118.5 (4)
N3—Li2—N8120.4 (4)C19—C20—H20120.8
N7—Li2—N884.9 (3)C21—C20—H20120.8
N3—Li2—N477.5 (2)C22—C21—C20121.0 (4)
N7—Li2—N4114.2 (3)C22—C21—H21119.5
N8—Li2—N4130.1 (3)C20—C21—H21119.5
N1—Si1—N2101.80 (15)C21—C22—C17122.2 (4)
N1—Si1—C14119.66 (16)C21—C22—H22118.9
N2—Si1—C14103.43 (16)C17—C22—H22118.9
N1—Si1—C13115.28 (15)C24—C23—C17132.1 (4)
N2—Si1—C13110.19 (16)C24—C23—H23113.9
C14—Si1—C13105.59 (16)C17—C23—H23113.9
N3—Si2—N4101.99 (15)C23—C24—N3125.8 (4)
N3—Si2—C29114.94 (16)C23—C24—C25117.6 (4)
N4—Si2—C29111.60 (17)N3—C24—C25116.5 (3)
N3—Si2—C30119.26 (17)C26—C25—C28109.3 (4)
N4—Si2—C30104.52 (18)C26—C25—C27107.2 (4)
C29—Si2—C30104.14 (19)C28—C25—C27104.7 (4)
C8—N1—Si1142.4 (2)C26—C25—C24111.9 (4)
C8—N1—Li1121.2 (3)C28—C25—C24116.1 (4)
Si1—N1—Li194.3 (2)C27—C25—C24107.1 (3)
C15—N2—C16107.8 (3)C25—C26—H26A109.5
C15—N2—Si1116.9 (2)C25—C26—H26B109.5
C16—N2—Si1119.7 (3)H26A—C26—H26B109.5
C15—N2—Li192.8 (3)C25—C26—H26C109.5
C16—N2—Li1136.1 (3)H26A—C26—H26C109.5
Si1—N2—Li180.77 (19)H26B—C26—H26C109.5
C24—N3—Si2134.2 (3)C25—C27—H27A109.5
C24—N3—Li2131.4 (3)C25—C27—H27B109.5
Si2—N3—Li294.3 (2)H27A—C27—H27B109.5
C31—N4—C32108.6 (3)C25—C27—H27C109.5
C31—N4—Si2116.0 (2)H27A—C27—H27C109.5
C32—N4—Si2118.4 (3)H27B—C27—H27C109.5
C31—N4—Li2103.2 (3)C25—C28—H28A109.5
C32—N4—Li2124.3 (3)C25—C28—H28B109.5
Si2—N4—Li284.3 (2)H28A—C28—H28B109.5
C33—N5—C35111.2 (3)C25—C28—H28C109.5
C33—N5—C34108.6 (3)H28A—C28—H28C109.5
C35—N5—C34107.2 (3)H28B—C28—H28C109.5
C33—N5—Li1105.6 (3)Si2—C29—H29A109.5
C35—N5—Li1104.3 (3)Si2—C29—H29B109.5
C34—N5—Li1119.9 (3)H29A—C29—H29B109.5
C37—N6—C36108.9 (3)Si2—C29—H29C109.5
C37—N6—C38108.8 (3)H29A—C29—H29C109.5
C36—N6—C38110.5 (3)H29B—C29—H29C109.5
C37—N6—Li1119.3 (3)Si2—C30—H30A109.5
C36—N6—Li1103.8 (3)Si2—C30—H30B109.5
C38—N6—Li1105.3 (3)H30A—C30—H30B109.5
C41—N7—C40111.2 (4)Si2—C30—H30C109.5
C41—N7—C39109.5 (4)H30A—C30—H30C109.5
C40—N7—C39107.4 (3)H30B—C30—H30C109.5
C41—N7—Li2102.8 (3)N4—C31—H31A109.5
C40—N7—Li2105.2 (3)N4—C31—H31B109.5
C39—N7—Li2120.7 (3)H31A—C31—H31B109.5
C43—N8—C42109.5 (3)N4—C31—H31C109.5
C43—N8—C44108.8 (3)H31A—C31—H31C109.5
C42—N8—C44110.4 (3)H31B—C31—H31C109.5
C43—N8—Li2121.3 (3)N4—C32—H32A109.5
C42—N8—Li2106.1 (3)N4—C32—H32B109.5
C44—N8—Li2100.2 (3)H32A—C32—H32B109.5
C2—C1—C6117.5 (4)N4—C32—H32C109.5
C2—C1—C7123.7 (4)H32A—C32—H32C109.5
C6—C1—C7118.8 (4)H32B—C32—H32C109.5
C3—C2—C1121.1 (4)N5—C33—H33A109.5
C3—C2—H2119.4N5—C33—H33B109.5
C1—C2—H2119.4H33A—C33—H33B109.5
C4—C3—C2121.5 (4)N5—C33—H33C109.5
C4—C3—H3119.2H33A—C33—H33C109.5
C2—C3—H3119.2H33B—C33—H33C109.5
C3—C4—C5117.6 (4)N5—C34—H34A109.5
C3—C4—H4121.2N5—C34—H34B109.5
C5—C4—H4121.2H34A—C34—H34B109.5
C6—C5—C4121.5 (4)N5—C34—H34C109.5
C6—C5—H5119.3H34A—C34—H34C109.5
C4—C5—H5119.3H34B—C34—H34C109.5
C5—C6—C1120.7 (4)N5—C35—C36110.8 (3)
C5—C6—H6119.7N5—C35—H35A109.5
C1—C6—H6119.7C36—C35—H35A109.5
C8—C7—C1128.8 (4)N5—C35—H35B109.5
C8—C7—H7115.6C36—C35—H35B109.5
C1—C7—H7115.6H35A—C35—H35B108.1
C7—C8—N1124.5 (4)N6—C36—C35111.6 (3)
C7—C8—C9118.0 (3)N6—C36—H36A109.3
N1—C8—C9117.4 (3)C35—C36—H36A109.3
C11—C9—C12109.7 (3)N6—C36—H36B109.3
C11—C9—C10107.1 (3)C35—C36—H36B109.3
C12—C9—C10107.0 (3)H36A—C36—H36B108.0
C11—C9—C8107.5 (3)N6—C37—H37A109.5
C12—C9—C8110.4 (3)N6—C37—H37B109.5
C10—C9—C8115.0 (3)H37A—C37—H37B109.5
C9—C10—H10A109.5N6—C37—H37C109.5
C9—C10—H10B109.5H37A—C37—H37C109.5
H10A—C10—H10B109.5H37B—C37—H37C109.5
C9—C10—H10C109.5N6—C38—H38A109.5
H10A—C10—H10C109.5N6—C38—H38B109.5
H10B—C10—H10C109.5H38A—C38—H38B109.5
C9—C11—H11A109.5N6—C38—H38C109.5
C9—C11—H11B109.5H38A—C38—H38C109.5
H11A—C11—H11B109.5H38B—C38—H38C109.5
C9—C11—H11C109.5N7—C39—H39A109.5
H11A—C11—H11C109.5N7—C39—H39B109.5
H11B—C11—H11C109.5H39A—C39—H39B109.5
C9—C12—H12A109.5N7—C39—H39C109.5
C9—C12—H12B109.5H39A—C39—H39C109.5
H12A—C12—H12B109.5H39B—C39—H39C109.5
C9—C12—H12C109.5N7—C40—H40A109.5
H12A—C12—H12C109.5N7—C40—H40B109.5
H12B—C12—H12C109.5H40A—C40—H40B109.5
Si1—C13—H13A109.5N7—C40—H40C109.5
Si1—C13—H13B109.5H40A—C40—H40C109.5
H13A—C13—H13B109.5H40B—C40—H40C109.5
Si1—C13—H13C109.5N7—C41—C42111.9 (4)
H13A—C13—H13C109.5N7—C41—H41A109.2
H13B—C13—H13C109.5C42—C41—H41A109.2
Si1—C14—H14A109.5N7—C41—H41B109.2
Si1—C14—H14B109.5C42—C41—H41B109.2
H14A—C14—H14B109.5H41A—C41—H41B107.9
Si1—C14—H14C109.5N8—C42—C41111.7 (4)
H14A—C14—H14C109.5N8—C42—H42A109.3
H14B—C14—H14C109.5C41—C42—H42A109.3
N2—C15—H15A109.5N8—C42—H42B109.3
N2—C15—H15B109.5C41—C42—H42B109.3
H15A—C15—H15B109.5H42A—C42—H42B107.9
N2—C15—H15C109.5N8—C43—H43A109.5
H15A—C15—H15C109.5N8—C43—H43B109.5
H15B—C15—H15C109.5H43A—C43—H43B109.5
N2—C16—H16A109.5N8—C43—H43C109.5
N2—C16—H16B109.5H43A—C43—H43C109.5
H16A—C16—H16B109.5H43B—C43—H43C109.5
N2—C16—H16C109.5N8—C44—H44A109.5
H16A—C16—H16C109.5N8—C44—H44B109.5
H16B—C16—H16C109.5H44A—C44—H44B109.5
C18—C17—C22115.3 (4)N8—C44—H44C109.5
C18—C17—C23119.4 (4)H44A—C44—H44C109.5
C22—C17—C23125.2 (4)H44B—C44—H44C109.5

Experimental details

Crystal data
Chemical formula[Li(C16H27N2Si)(C6H16N2)]
Mr398.63
Crystal system, space groupMonoclinic, P21
Temperature (K)178
a, b, c (Å)14.819 (3), 9.4142 (16), 18.635 (3)
β (°) 97.674 (3)
V3)2576.4 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.40 × 0.30 × 0.30
Data collection
DiffractometerBruker CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.960, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
10666, 8386, 4772
Rint0.043
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.066, 0.83
No. of reflections8386
No. of parameters527
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.25
Absolute structureFlack (1983)
Absolute structure parameter0.05 (11)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top
Li2—N32.013 (7)Si2—C291.876 (3)
Li2—N72.143 (7)Si2—C301.876 (4)
Li2—N82.137 (7)N3—C241.383 (4)
Li2—N42.220 (7)N4—C311.467 (4)
Si2—N31.649 (3)N4—C321.480 (4)
Si2—N41.766 (3)
N3—Li2—N7136.9 (4)C24—N3—Li2131.4 (3)
N3—Li2—N8120.4 (4)Si2—N3—Li294.3 (2)
N7—Li2—N884.9 (3)C31—N4—C32108.6 (3)
N3—Li2—N477.5 (2)C31—N4—Si2116.0 (2)
N7—Li2—N4114.2 (3)C32—N4—Si2118.4 (3)
N8—Li2—N4130.1 (3)C31—N4—Li2103.2 (3)
N3—Si2—N4101.99 (15)C32—N4—Li2124.3 (3)
N3—Si2—C29114.94 (16)Si2—N4—Li284.3 (2)
N4—Si2—C29111.60 (17)C24—C23—C17132.1 (4)
N3—Si2—C30119.26 (17)C23—C24—N3125.8 (4)
N4—Si2—C30104.52 (18)C23—C24—C25117.6 (4)
C29—Si2—C30104.14 (19)N3—C24—C25116.5 (3)
C24—N3—Si2134.2 (3)
 

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