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The title compound, [Li2(C13H22N2Si)2(C4H10O)2], possesses a dinuclear structure featuring four-coordinate Li atoms, each of which shows a further, weak, contact to the central C atom of the NCN linkage of the amidinate ligand. The mol­ecules possess crystallographically imposed inversion symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017579/bt6195sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017579/bt6195Isup2.hkl
Contains datablock I

CCDC reference: 198321

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.042
  • Data-to-parameter ratio = 20.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C3 -H31 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C4 -H41 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C5 -H51 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C6 -H61 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C7 -H71 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C8 -H81 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C8 -H82 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C9 -H91 1.555 1.555 PLAT_741 Alert C Bond Calc 1.001(3), Rep 1.00000 .... Missing s.u. C9 -H92 1.555 1.555 PLAT_741 Alert C Bond Calc 1.001(3), Rep 1.00000 .... Missing s.u. C10 -H101 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C10 -H102 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C10 -H103 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C11 -H111 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C11 -H112 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C11 -H113 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C12 -H121 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C12 -H122 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C12 -H123 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C13 -H131 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C13 -H132 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C13 -H133 1.555 1.555 PLAT_741 Alert C Bond Calc 0.999(3), Rep 1.00000 .... Missing s.u. C14 -H141 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C14 -H142 1.555 1.555 PLAT_741 Alert C Bond Calc 1.001(3), Rep 1.00000 .... Missing s.u. C14 -H143 1.555 1.555 PLAT_741 Alert C Bond Calc 0.999(3), Rep 1.00000 .... Missing s.u. C15 -H151 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C15 -H152 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C16 -H161 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C16 -H162 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C17 -H171 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(4), Rep 1.00000 .... Missing s.u. C17 -H172 1.555 1.555 PLAT_741 Alert C Bond Calc 1.000(3), Rep 1.00000 .... Missing s.u. C17 -H173 1.555 1.555 PLAT_742 Alert C Angle Calc 119.6(2), Rep 119.62 .... Missing su C2 -C3 -H31 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 120.2(2), Rep 120.24 .... Missing su C4 -C3 -H31 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 119.6(3), Rep 119.56 .... Missing su C3 -C4 -H41 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 119.9(3), Rep 119.88 .... Missing su C5 -C4 -H41 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 120.1(3), Rep 120.05 .... Missing su C4 -C5 -H51 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 120.3(3), Rep 120.31 .... Missing su C6 -C5 -H51 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 120.0(2), Rep 120.02 .... Missing su C5 -C6 -H61 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 119.9(2), Rep 119.82 .... Missing su C7 -C6 -H61 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 119.4(2), Rep 119.36 .... Missing su C2 -C7 -H71 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 120.0(2), Rep 120.06 .... Missing su C6 -C7 -H71 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.7(2), Rep 108.73 .... Missing su N2 -C8 -H81 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.30(19), Rep 108.30 .... Missing su C9 -C8 -H81 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.55(19), Rep 108.55 .... Missing su N2 -C8 -H82 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.5(2), Rep 108.50 .... Missing su C9 -C8 -H82 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(2), Rep 109.47 .... Missing su H81 -C8 -H82 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.7(2), Rep 108.70 .... Missing su C8 -C9 -H91 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.8(2), Rep 108.79 .... Missing su C10 -C9 -H91 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.7(2), Rep 108.70 .... Missing su C8 -C9 -H92 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.8(2), Rep 108.80 .... Missing su C10 -C9 -H92 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(2), Rep 109.47 .... Missing su H91 -C9 -H92 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 110.2(3), Rep 110.21 .... Missing su C9 -C10 -H101 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.1(2), Rep 109.10 .... Missing su C9 -C10 -H102 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H101 -C10 -H102 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.1(2), Rep 109.09 .... Missing su C9 -C10 -H103 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H101 -C10 -H103 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H102 -C10 -H103 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(2), Rep 109.54 .... Missing su SI1 -C11 -H111 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.2(2), Rep 109.21 .... Missing su SI1 -C11 -H112 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H111 -C11 -H112 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.7(2), Rep 109.65 .... Missing su SI1 -C11 -H113 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H111 -C11 -H113 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H112 -C11 -H113 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.8(2), Rep 109.76 .... Missing su SI1 -C12 -H121 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.22(19), Rep 109.22 .... Missing su SI1 -C12 -H122 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H121 -C12 -H122 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.40(19), Rep 109.42 .... Missing su SI1 -C12 -H123 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H121 -C12 -H123 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H122 -C12 -H123 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(2), Rep 109.50 .... Missing su SI1 -C13 -H131 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.6(2), Rep 109.55 .... Missing su SI1 -C13 -H132 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.47 .... Missing su H131 -C13 -H132 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.4(2), Rep 109.36 .... Missing su SI1 -C13 -H133 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.4(3), Rep 109.48 .... Missing su H131 -C13 -H133 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.4(3), Rep 109.48 .... Missing su H132 -C13 -H133 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 110.2(3), Rep 110.17 .... Missing su C15 -C14 -H141 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.9(2), Rep 108.86 .... Missing su C15 -C14 -H142 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H141 -C14 -H142 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.4(2), Rep 109.37 .... Missing su C15 -C14 -H143 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.4(3), Rep 109.48 .... Missing su H141 -C14 -H143 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.4(3), Rep 109.48 .... Missing su H142 -C14 -H143 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(2), Rep 109.45 .... Missing su O1 -C15 -H151 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.6(2), Rep 109.64 .... Missing su C14 -C15 -H151 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.3(2), Rep 109.28 .... Missing su O1 -C15 -H152 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.1(2), Rep 109.14 .... Missing su C14 -C15 -H152 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.47 .... Missing su H151 -C15 -H152 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.66(19), Rep 108.70 .... Missing su O1 -C16 -H161 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.6(2), Rep 108.63 .... Missing su C17 -C16 -H161 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.0(2), Rep 109.00 .... Missing su O1 -C16 -H162 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 108.9(2), Rep 108.87 .... Missing su C17 -C16 -H162 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(2), Rep 109.47 .... Missing su H161 -C16 -H162 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 110.0(2), Rep 109.97 .... Missing su C16 -C17 -H171 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.3(2), Rep 109.33 .... Missing su C16 -C17 -H172 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H171 -C17 -H172 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.1(2), Rep 109.09 .... Missing su C16 -C17 -H173 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H171 -C17 -H173 1.555 1.555 1.555 PLAT_742 Alert C Angle Calc 109.5(3), Rep 109.48 .... Missing su H172 -C17 -H173 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
97 Alert Level C = Please check

Comment top

In recent years, there has been much interest in N-silylated benzamidinates (Edelmann, 1994). New types of amidinate ligands with pendant amine or pyridine functionalities have recently been reported (Brandsma et al., 1998; Doyle et al., 2000; Kincaid et al., 1999). We have been interested in developing the chemistry of pendant-arm-functionalized amidinates as supporting ligands for group 4 imido chemistry (Boyd et al., 2002). As part of these studies, we were interested in using an N-propyl-substituted benzamidinate ligand, namely Me3SiNC(Ph)NCH2CH2CH3, for comparison with the pendant alkylamine-substituted amidinates Me3SiNC(Ph)NCH2CH2NMe2 and Me3SiNC(Ph)NCH2CH2CH2NMe2 (Brandsma et al., 1998; Doyle et al., 2000). We describe here the structure of the diethyl ether adduct of the lithium salt of this ligand, (I).

Molecules of (I) adopt a dinuclear structure in the solid state, possessing crystallographically imposed Ci molecular symmetry. Each Li atom, and each propyl-substituted benzamidinate N atom, is four-coordinated, with Li deviating the most from an ideal tetrahedral geometry due to the restricted bite angle of the amidinate group. The central motif of the structure is a four-membered ring of alternating Li and N atoms, which is planar by symmetry. To either end of this ring is fused another, slightly-puckered, four-membered ring. This puckering sees atoms C1 and Li lying out of the Li1/N1/C1/N2 least-squares plane of the ring by ca 0.19 and 0.07 Å, respectively. This creates a close Li1···C1 contact of 2.334 (3) Å which is possibly electrostatic in nature. This distance is at the lower end of Li···CN2 distances observed for other lithiated amidinates, which are in the range ca 2.30–2.42 Å (Fletcher et al., 1996). The Li—N distances and N—Li—N angles in (I) span the typical ranges reported for lithiated amides (Fletcher et al., 1996; Allen & Kennard, 1993).

The structural motif in (I) is closely related to that of the Li salt of the pendant N-propylamine-substituted ligand, namely Li2{Me3SiNC(Ph)NCH2CH2CH2NMe2}2, synthesized by Lappert and co-workers (Doyle et al., 2000). In this case, there is no Et2O coordinated to Li and the remaining site is occupied by the chelating pendant amine N-donor.

Experimental top

The title compound was prepared according to previously described procedures (Boyd et al., 2002). Crystallization of the crude product from a mixture of hexane and Et2O afforded the title compound as air-sensitive colourless blocks.

Refinement top

All H atoms were placed geometrically. Refinement was carried out against 4117 data with I 0.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO; data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 2001); molecular graphics: CAMERON (Watkin et al., 2001); software used to prepare material for publication: CRYSTALS.

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I). Displacement parameters are drawn at the 20% probability level and H atoms have been omitted for clarity. Atoms carrying the suffix A are related to their counterparts by the symmetry code (1 − x, 1 − y, 2 − z).
Bis(µ-N-n-propyl-N-trimethylsilylbenzamidinato)bis[(diethyl ether-O)lithium] top
Crystal data top
[Li2(C13H22N2Si)2(C4H10O)2]Z = 1
Mr = 628.94F(000) = 344.000
Triclinic, P1Dx = 1.078 Mg m3
a = 8.4111 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.486 (2) ÅCell parameters from 3991 reflections
c = 11.774 (2) Åθ = 5–27°
α = 106.59 (3)°µ = 0.12 mm1
β = 96.05 (3)°T = 150 K
γ = 99.38 (3)°Block, colourless
V = 969.2 (4) Å30.32 × 0.28 × 0.28 mm
Data collection top
Enraf-Nonius KappaCCD
diffractometer
2907 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.02
ϕ and ω scansθmax = 27.5°, θmin = 5.1°
Absorption correction: multi-scan
DENZO (Otwinowski & Minor, 1997)
h = 1010
Tmin = 0.97, Tmax = 0.97k = 1313
7923 measured reflectionsl = 1415
4372 independent reflections
Refinement top
Refinement on FPrimary atom site location: direct methods
Least-squares matrix: fullHydrogen site location: geometric
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.042 Prince modified Chebychev polynomial (Watkin, 1994), W = [weight][1-(ΔF/6σF)2]2, with -0.679 -2.35 -1.48 -0.984 -0.429
S = 1.05(Δ/σ)max = 0.0003
4117 reflectionsΔρmax = 0.39 e Å3
199 parametersΔρmin = 0.47 e Å3
0 restraints
Crystal data top
[Li2(C13H22N2Si)2(C4H10O)2]γ = 99.38 (3)°
Mr = 628.94V = 969.2 (4) Å3
Triclinic, P1Z = 1
a = 8.4111 (17) ÅMo Kα radiation
b = 10.486 (2) ŵ = 0.12 mm1
c = 11.774 (2) ÅT = 150 K
α = 106.59 (3)°0.32 × 0.28 × 0.28 mm
β = 96.05 (3)°
Data collection top
Enraf-Nonius KappaCCD
diffractometer
4372 independent reflections
Absorption correction: multi-scan
DENZO (Otwinowski & Minor, 1997)
2907 reflections with I > 2σ(I)
Tmin = 0.97, Tmax = 0.97Rint = 0.02
7923 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.042H-atom parameters constrained
S = 1.05Δρmax = 0.39 e Å3
4117 reflectionsΔρmin = 0.47 e Å3
199 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Li10.4338 (4)0.5154 (3)0.9058 (3)0.0291
N10.48608 (18)0.34673 (15)0.79445 (13)0.0256
N20.38630 (18)0.34084 (15)0.96694 (13)0.0256
O10.23336 (16)0.58181 (14)0.87477 (11)0.0332
Si10.55364 (6)0.29411 (6)0.66023 (4)0.0284
C10.3952 (2)0.27907 (17)0.85265 (15)0.0243
C20.2989 (2)0.13717 (18)0.78689 (15)0.0259
C30.3693 (2)0.02470 (19)0.78300 (17)0.0319
C40.2847 (3)0.1046 (2)0.71626 (19)0.0396
C50.1290 (3)0.1239 (2)0.65442 (18)0.0403
C60.0573 (2)0.0130 (2)0.65930 (18)0.0385
C70.1418 (2)0.1168 (2)0.72489 (18)0.0338
C80.2709 (2)0.27532 (19)1.02876 (16)0.0277
C90.3518 (2)0.2094 (2)1.11195 (18)0.0350
C100.2343 (3)0.1571 (2)1.18636 (19)0.0411
C110.7231 (3)0.2005 (2)0.67087 (18)0.0386
C120.3989 (3)0.1847 (2)0.52779 (17)0.0450
C130.6403 (3)0.4523 (2)0.62602 (19)0.0394
C140.1588 (3)0.4841 (2)0.66233 (19)0.0474
C150.1012 (3)0.5436 (2)0.77804 (19)0.0419
C160.1902 (2)0.6552 (2)0.98717 (17)0.0360
C170.1981 (3)0.8032 (2)0.9993 (2)0.0442
H310.4813 (2)0.03798 (19)0.82822 (17)0.0394*
H410.3366 (3)0.1845 (2)0.71336 (19)0.0450*
H510.0688 (3)0.2175 (2)0.60636 (18)0.0458*
H610.0552 (2)0.0263 (2)0.61487 (18)0.0425*
H710.0895 (2)0.1967 (2)0.72875 (18)0.0406*
H810.2168 (2)0.34545 (19)1.07744 (16)0.0366*
H820.1867 (2)0.20385 (19)0.96695 (16)0.0366*
H910.4450 (2)0.2780 (2)1.16757 (18)0.0476*
H920.3939 (2)0.1313 (2)1.06246 (18)0.0476*
H1010.2916 (3)0.1143 (2)1.24002 (19)0.0557*
H1020.1922 (3)0.2349 (2)1.23622 (19)0.0557*
H1030.1410 (3)0.0882 (2)1.13112 (19)0.0557*
H1110.7597 (3)0.1714 (2)0.59101 (18)0.0493*
H1120.8166 (3)0.2618 (2)0.73191 (18)0.0493*
H1130.6840 (3)0.1187 (2)0.69559 (18)0.0493*
H1210.4527 (3)0.1606 (2)0.45493 (17)0.0512*
H1220.3495 (3)0.0998 (2)0.54444 (17)0.0512*
H1230.3115 (3)0.2352 (2)0.51359 (17)0.0512*
H1310.6822 (3)0.4276 (2)0.54789 (19)0.0499*
H1320.7317 (3)0.5085 (2)0.69142 (19)0.0499*
H1330.5530 (3)0.5056 (2)0.62041 (19)0.0499*
H1410.0663 (3)0.4568 (2)0.59397 (19)0.0569*
H1420.2463 (3)0.5537 (2)0.65028 (19)0.0569*
H1430.2041 (3)0.4025 (2)0.66583 (19)0.0569*
H1510.0562 (3)0.6253 (2)0.77504 (19)0.0481*
H1520.0139 (3)0.4742 (2)0.79059 (19)0.0481*
H1610.2681 (2)0.6485 (2)1.05450 (17)0.0455*
H1620.0767 (2)0.6132 (2)0.99236 (17)0.0455*
H1710.1680 (3)0.8508 (2)1.0781 (2)0.0539*
H1720.3115 (3)0.8460 (2)0.9946 (2)0.0539*
H1730.1201 (3)0.8107 (2)0.9324 (2)0.0539*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Li10.0318 (16)0.0257 (15)0.0263 (15)0.0074 (12)0.0018 (12)0.0027 (12)
N10.0269 (7)0.0246 (7)0.0234 (7)0.0037 (6)0.0050 (6)0.0047 (6)
N20.0272 (8)0.0259 (8)0.0232 (7)0.0051 (6)0.0048 (6)0.0068 (6)
O10.0288 (7)0.0401 (8)0.0286 (7)0.0116 (6)0.0003 (5)0.0060 (6)
Si10.0266 (3)0.0322 (3)0.0225 (2)0.0036 (2)0.00445 (19)0.0035 (2)
C10.0219 (8)0.0244 (8)0.0254 (8)0.0062 (6)0.0020 (6)0.0056 (7)
C20.0260 (9)0.0267 (9)0.0236 (8)0.0033 (7)0.0050 (7)0.0063 (7)
C30.032 (1)0.029 (1)0.032 (1)0.0058 (8)0.0035 (8)0.0071 (8)
C40.0461 (12)0.026 (1)0.0429 (12)0.0047 (9)0.0096 (9)0.0051 (8)
C50.0448 (12)0.031 (1)0.0350 (11)0.0053 (9)0.0076 (9)0.0009 (8)
C60.030 (1)0.0431 (12)0.032 (1)0.0061 (8)0.0015 (8)0.0064 (9)
C70.0278 (9)0.034 (1)0.037 (1)0.0041 (8)0.0023 (8)0.0081 (8)
C80.0260 (9)0.0297 (9)0.0275 (9)0.0061 (7)0.0070 (7)0.0080 (7)
C90.035 (1)0.0382 (11)0.036 (1)0.0084 (8)0.0086 (8)0.0156 (9)
C100.0487 (13)0.0405 (12)0.0418 (12)0.009 (1)0.017 (1)0.021 (1)
C110.0389 (11)0.0413 (12)0.0375 (11)0.0150 (9)0.0132 (9)0.0089 (9)
C120.0405 (12)0.0562 (14)0.024 (1)0.000 (1)0.0030 (8)0.0034 (9)
C130.0411 (12)0.0440 (12)0.0356 (11)0.0056 (9)0.0101 (9)0.0167 (9)
C140.0529 (14)0.0522 (14)0.0319 (11)0.0142 (11)0.0040 (9)0.007 (1)
C150.031 (1)0.0489 (13)0.0376 (11)0.0054 (9)0.0055 (8)0.0063 (9)
C160.033 (1)0.0443 (12)0.031 (1)0.0116 (9)0.0052 (8)0.0083 (9)
C170.0421 (12)0.0394 (12)0.0444 (12)0.0089 (9)0.0045 (9)0.003 (1)
Geometric parameters (Å, º) top
Li1—N12.023 (3)C8—H821.000
Li1—N22.145 (3)C9—C101.525 (3)
Li1—N2i2.073 (3)C9—H911.000
Li1—O11.965 (3)C9—H921.000
Li1—C12.334 (3)C10—H1011.000
N1—Si11.7083 (15)C10—H1021.000
N1—C11.330 (2)C10—H1031.000
N2—C11.332 (2)C11—H1111.000
N2—C81.470 (2)C11—H1121.000
O1—C151.421 (2)C11—H1131.000
O1—C161.444 (2)C12—H1211.000
Si1—C111.871 (2)C12—H1221.000
Si1—C121.872 (2)C12—H1231.000
Si1—C131.870 (2)C13—H1311.000
C1—C21.512 (2)C13—H1321.000
C2—C31.395 (3)C13—H1331.000
C2—C71.393 (3)C14—C151.494 (3)
C3—C41.386 (3)C14—H1411.000
C3—H311.000C14—H1421.000
C4—C51.384 (3)C14—H1431.000
C4—H411.000C15—H1511.000
C5—C61.384 (3)C15—H1521.000
C5—H511.000C16—C171.507 (3)
C6—C71.387 (3)C16—H1611.000
C6—H611.000C16—H1621.000
C7—H711.000C17—H1711.000
C8—C91.516 (3)C17—H1721.000
C8—H811.000C17—H1731.000
N1—Li1—N266.61 (11)C10—C9—H91108.79
N1—Li1—N2i121.29 (16)C8—C9—H92108.7
N2—Li1—N2i107.22 (14)C10—C9—H92108.80
N1—Li1—O1123.08 (16)H91—C9—H92109.467
N2—Li1—O1111.49 (16)C9—C10—H101110.21
N2i—Li1—O1113.47 (15)C9—C10—H102109.10
Li1—N1—Si1140.05 (12)H101—C10—H102109.476
Li1—N1—C185.59 (14)C9—C10—H103109.09
Si1—N1—C1131.63 (13)H101—C10—H103109.476
Li1—N2—Li1i72.78 (14)H102—C10—H103109.476
Li1—N2—C180.64 (13)Si1—C11—H111109.54
Li1i—N2—C1127.44 (15)Si1—C11—H112109.21
Li1—N2—C8141.30 (14)H111—C11—H112109.476
Li1i—N2—C8108.94 (14)Si1—C11—H113109.65
C1—N2—C8119.81 (15)H111—C11—H113109.476
Li1—O1—C15134.78 (15)H112—C11—H113109.476
Li1—O1—C16109.67 (14)Si1—C12—H121109.76
C15—O1—C16112.43 (15)Si1—C12—H122109.22
N1—Si1—C11111.66 (9)H121—C12—H122109.476
N1—Si1—C12117.17 (9)Si1—C12—H123109.42
C11—Si1—C12106.78 (11)H121—C12—H123109.476
N1—Si1—C13105.94 (9)H122—C12—H123109.476
C11—Si1—C13107.1 (1)Si1—C13—H131109.50
C12—Si1—C13107.7 (1)Si1—C13—H132109.55
N1—C1—N2118.71 (16)H131—C13—H132109.475
N1—C1—C2119.68 (15)Si1—C13—H133109.36
N2—C1—C2121.55 (15)H131—C13—H133109.476
C1—C2—C3120.25 (16)H132—C13—H133109.476
C1—C2—C7120.77 (16)C15—C14—H141110.17
C3—C2—C7118.91 (17)C15—C14—H142108.86
C2—C3—C4120.14 (19)H141—C14—H142109.476
C2—C3—H31119.62C15—C14—H143109.37
C4—C3—H31120.24H141—C14—H143109.476
C3—C4—C5120.6 (2)H142—C14—H143109.476
C3—C4—H41119.56O1—C15—C14109.84 (17)
C5—C4—H41119.88O1—C15—H151109.45
C4—C5—C6119.64 (18)C14—C15—H151109.64
C4—C5—H51120.05O1—C15—H152109.28
C6—C5—H51120.31C14—C15—H152109.14
C5—C6—C7120.16 (19)H151—C15—H152109.467
C5—C6—H61120.02O1—C16—C17112.18 (17)
C7—C6—H61119.82O1—C16—H161108.7
C2—C7—C6120.58 (9)C17—C16—H161108.63
C2—C7—H71119.36O1—C16—H162109.0
C6—C7—H71120.06C17—C16—H162108.87
N2—C8—C9113.22 (15)H161—C16—H162109.467
N2—C8—H81108.73C16—C17—H171109.97
C9—C8—H81108.3C16—C17—H172109.33
N2—C8—H82108.55H171—C17—H172109.476
C9—C8—H82108.5C16—C17—H173109.09
H81—C8—H82109.467H171—C17—H173109.476
C8—C9—C10112.37 (17)H172—C17—H173109.476
C8—C9—H91108.7
Symmetry code: (i) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formula[Li2(C13H22N2Si)2(C4H10O)2]
Mr628.94
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)8.4111 (17), 10.486 (2), 11.774 (2)
α, β, γ (°)106.59 (3), 96.05 (3), 99.38 (3)
V3)969.2 (4)
Z1
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.32 × 0.28 × 0.28
Data collection
DiffractometerEnraf-Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
DENZO (Otwinowski & Minor, 1997)
Tmin, Tmax0.97, 0.97
No. of measured, independent and
observed [I > 2σ(I)] reflections
7923, 4372, 2907
Rint0.02
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.042, 1.05
No. of reflections4117
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.47

Computer programs: COLLECT (Nonius, 2000), DENZO (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), CRYSTALS (Watkin et al., 2001), CAMERON (Watkin et al., 2001), CRYSTALS.

Selected geometric parameters (Å, º) top
Li1—N12.023 (3)N1—Si11.7083 (15)
Li1—N22.145 (3)N1—C11.330 (2)
Li1—N2i2.073 (3)N2—C11.332 (2)
Li1—O11.965 (3)N2—C81.470 (2)
Li1—C12.334 (3)C1—C21.512 (2)
N1—Li1—N266.61 (11)Li1i—N2—C1127.44 (15)
N1—Li1—N2i121.29 (16)Li1—N2—C8141.30 (14)
N2—Li1—N2i107.22 (14)Li1i—N2—C8108.94 (14)
N1—Li1—O1123.08 (16)C1—N2—C8119.81 (15)
N2—Li1—O1111.49 (16)Li1—O1—C15134.78 (15)
N2i—Li1—O1113.47 (15)Li1—O1—C16109.67 (14)
Li1—N1—Si1140.05 (12)C15—O1—C16112.43 (15)
Li1—N1—C185.59 (14)N1—C1—N2118.71 (16)
Si1—N1—C1131.63 (13)N1—C1—C2119.68 (15)
Li1—N2—Li1i72.78 (14)N2—C1—C2121.55 (15)
Li1—N2—C180.64 (13)
Symmetry code: (i) x+1, y+1, z+2.
 

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