Bis(μ-N-n-propyl-N-tri­methyl­silyl­benzamidinato)­bis­[(diethyl ether-O)­lithium]

Boyd, C.L.; Tyrrell, B.R.; Mountford, P.

doi:10.1107/S1600536802017579

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Bis(μ-N-n-propyl-N-trimethylsilylbenzamidinato)bis[(diethyl ether-O)lithium]

C. L. Boyd, B. R. Tyrrell and P. Mountford

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017579/bt6195sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017579/bt6195Isup2.hkl Contains datablock I

CCDC reference: 198321

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (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


 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 C_i 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.

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

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
M_r = 628.94	F(000) = 344.000
Triclinic, P1	D_x = 1.078 Mg m⁻³
a = 8.4111 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.486 (2) Å	Cell parameters from 3991 reflections
c = 11.774 (2) Å	θ = 5–27°
α = 106.59 (3)°	µ = 0.12 mm⁻¹
β = 96.05 (3)°	T = 150 K
γ = 99.38 (3)°	Block, colourless
V = 969.2 (4) Å³	0.32 × 0.28 × 0.28 mm

Data collection top

Enraf-Nonius KappaCCD diffractometer	2907 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.02
ϕ and ω scans	θ_max = 27.5°, θ_min = 5.1°
Absorption correction: multi-scan DENZO (Otwinowski & Minor, 1997)	h = −10→10
T_min = 0.97, T_max = 0.97	k = −13→13
7923 measured reflections	l = −14→15
4372 independent reflections

Refinement top

Refinement on F	Primary atom site location: direct methods
Least-squares matrix: full	Hydrogen site location: geometric
R[F² > 2σ(F²)] = 0.046	H-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 reflections	Δρ_max = 0.39 e Å⁻³
199 parameters	Δρ_min = −0.47 e Å⁻³
0 restraints

Crystal data top

[Li₂(C₁₃H₂₂N₂Si)₂(C₄H₁₀O)₂]	γ = 99.38 (3)°
M_r = 628.94	V = 969.2 (4) Å³
Triclinic, P1	Z = 1
a = 8.4111 (17) Å	Mo Kα radiation
b = 10.486 (2) Å	µ = 0.12 mm⁻¹
c = 11.774 (2) Å	T = 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)
T_min = 0.97, T_max = 0.97	R_int = 0.02
7923 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.042	H-atom parameters constrained
S = 1.05	Δρ_max = 0.39 e Å⁻³
4117 reflections	Δρ_min = −0.47 e Å⁻³
199 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Li1	0.4338 (4)	0.5154 (3)	0.9058 (3)	0.0291
N1	0.48608 (18)	0.34673 (15)	0.79445 (13)	0.0256
N2	0.38630 (18)	0.34084 (15)	0.96694 (13)	0.0256
O1	0.23336 (16)	0.58181 (14)	0.87477 (11)	0.0332
Si1	0.55364 (6)	0.29411 (6)	0.66023 (4)	0.0284
C1	0.3952 (2)	0.27907 (17)	0.85265 (15)	0.0243
C2	0.2989 (2)	0.13717 (18)	0.78689 (15)	0.0259
C3	0.3693 (2)	0.02470 (19)	0.78300 (17)	0.0319
C4	0.2847 (3)	−0.1046 (2)	0.71626 (19)	0.0396
C5	0.1290 (3)	−0.1239 (2)	0.65442 (18)	0.0403
C6	0.0573 (2)	−0.0130 (2)	0.65930 (18)	0.0385
C7	0.1418 (2)	0.1168 (2)	0.72489 (18)	0.0338
C8	0.2709 (2)	0.27532 (19)	1.02876 (16)	0.0277
C9	0.3518 (2)	0.2094 (2)	1.11195 (18)	0.0350
C10	0.2343 (3)	0.1571 (2)	1.18636 (19)	0.0411
C11	0.7231 (3)	0.2005 (2)	0.67087 (18)	0.0386
C12	0.3989 (3)	0.1847 (2)	0.52779 (17)	0.0450
C13	0.6403 (3)	0.4523 (2)	0.62602 (19)	0.0394
C14	0.1588 (3)	0.4841 (2)	0.66233 (19)	0.0474
C15	0.1012 (3)	0.5436 (2)	0.77804 (19)	0.0419
C16	0.1902 (2)	0.6552 (2)	0.98717 (17)	0.0360
C17	0.1981 (3)	0.8032 (2)	0.9993 (2)	0.0442
H31	0.4813 (2)	0.03798 (19)	0.82822 (17)	0.0394*
H41	0.3366 (3)	−0.1845 (2)	0.71336 (19)	0.0450*
H51	0.0688 (3)	−0.2175 (2)	0.60636 (18)	0.0458*
H61	−0.0552 (2)	−0.0263 (2)	0.61487 (18)	0.0425*
H71	0.0895 (2)	0.1967 (2)	0.72875 (18)	0.0406*
H81	0.2168 (2)	0.34545 (19)	1.07744 (16)	0.0366*
H82	0.1867 (2)	0.20385 (19)	0.96695 (16)	0.0366*
H91	0.4450 (2)	0.2780 (2)	1.16757 (18)	0.0476*
H92	0.3939 (2)	0.1313 (2)	1.06246 (18)	0.0476*
H101	0.2916 (3)	0.1143 (2)	1.24002 (19)	0.0557*
H102	0.1922 (3)	0.2349 (2)	1.23622 (19)	0.0557*
H103	0.1410 (3)	0.0882 (2)	1.13112 (19)	0.0557*
H111	0.7597 (3)	0.1714 (2)	0.59101 (18)	0.0493*
H112	0.8166 (3)	0.2618 (2)	0.73191 (18)	0.0493*
H113	0.6840 (3)	0.1187 (2)	0.69559 (18)	0.0493*
H121	0.4527 (3)	0.1606 (2)	0.45493 (17)	0.0512*
H122	0.3495 (3)	0.0998 (2)	0.54444 (17)	0.0512*
H123	0.3115 (3)	0.2352 (2)	0.51359 (17)	0.0512*
H131	0.6822 (3)	0.4276 (2)	0.54789 (19)	0.0499*
H132	0.7317 (3)	0.5085 (2)	0.69142 (19)	0.0499*
H133	0.5530 (3)	0.5056 (2)	0.62041 (19)	0.0499*
H141	0.0663 (3)	0.4568 (2)	0.59397 (19)	0.0569*
H142	0.2463 (3)	0.5537 (2)	0.65028 (19)	0.0569*
H143	0.2041 (3)	0.4025 (2)	0.66583 (19)	0.0569*
H151	0.0562 (3)	0.6253 (2)	0.77504 (19)	0.0481*
H152	0.0139 (3)	0.4742 (2)	0.79059 (19)	0.0481*
H161	0.2681 (2)	0.6485 (2)	1.05450 (17)	0.0455*
H162	0.0767 (2)	0.6132 (2)	0.99236 (17)	0.0455*
H171	0.1680 (3)	0.8508 (2)	1.0781 (2)	0.0539*
H172	0.3115 (3)	0.8460 (2)	0.9946 (2)	0.0539*
H173	0.1201 (3)	0.8107 (2)	0.9324 (2)	0.0539*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Li1	0.0318 (16)	0.0257 (15)	0.0263 (15)	0.0074 (12)	0.0018 (12)	0.0027 (12)
N1	0.0269 (7)	0.0246 (7)	0.0234 (7)	0.0037 (6)	0.0050 (6)	0.0047 (6)
N2	0.0272 (8)	0.0259 (8)	0.0232 (7)	0.0051 (6)	0.0048 (6)	0.0068 (6)
O1	0.0288 (7)	0.0401 (8)	0.0286 (7)	0.0116 (6)	0.0003 (5)	0.0060 (6)
Si1	0.0266 (3)	0.0322 (3)	0.0225 (2)	0.0036 (2)	0.00445 (19)	0.0035 (2)
C1	0.0219 (8)	0.0244 (8)	0.0254 (8)	0.0062 (6)	0.0020 (6)	0.0056 (7)
C2	0.0260 (9)	0.0267 (9)	0.0236 (8)	0.0033 (7)	0.0050 (7)	0.0063 (7)
C3	0.032 (1)	0.029 (1)	0.032 (1)	0.0058 (8)	0.0035 (8)	0.0071 (8)
C4	0.0461 (12)	0.026 (1)	0.0429 (12)	0.0047 (9)	0.0096 (9)	0.0051 (8)
C5	0.0448 (12)	0.031 (1)	0.0350 (11)	−0.0053 (9)	0.0076 (9)	0.0009 (8)
C6	0.030 (1)	0.0431 (12)	0.032 (1)	−0.0061 (8)	−0.0015 (8)	0.0064 (9)
C7	0.0278 (9)	0.034 (1)	0.037 (1)	0.0041 (8)	0.0023 (8)	0.0081 (8)
C8	0.0260 (9)	0.0297 (9)	0.0275 (9)	0.0061 (7)	0.0070 (7)	0.0080 (7)
C9	0.035 (1)	0.0382 (11)	0.036 (1)	0.0084 (8)	0.0086 (8)	0.0156 (9)
C10	0.0487 (13)	0.0405 (12)	0.0418 (12)	0.009 (1)	0.017 (1)	0.021 (1)
C11	0.0389 (11)	0.0413 (12)	0.0375 (11)	0.0150 (9)	0.0132 (9)	0.0089 (9)
C12	0.0405 (12)	0.0562 (14)	0.024 (1)	0.000 (1)	0.0030 (8)	−0.0034 (9)
C13	0.0411 (12)	0.0440 (12)	0.0356 (11)	0.0056 (9)	0.0101 (9)	0.0167 (9)
C14	0.0529 (14)	0.0522 (14)	0.0319 (11)	0.0142 (11)	−0.0040 (9)	0.007 (1)
C15	0.031 (1)	0.0489 (13)	0.0376 (11)	0.0054 (9)	−0.0055 (8)	0.0063 (9)
C16	0.033 (1)	0.0443 (12)	0.031 (1)	0.0116 (9)	0.0052 (8)	0.0083 (9)
C17	0.0421 (12)	0.0394 (12)	0.0444 (12)	0.0089 (9)	0.0045 (9)	0.003 (1)

Geometric parameters (Å, º) top

Li1—N1	2.023 (3)	C8—H82	1.000
Li1—N2	2.145 (3)	C9—C10	1.525 (3)
Li1—N2ⁱ	2.073 (3)	C9—H91	1.000
Li1—O1	1.965 (3)	C9—H92	1.000
Li1—C1	2.334 (3)	C10—H101	1.000
N1—Si1	1.7083 (15)	C10—H102	1.000
N1—C1	1.330 (2)	C10—H103	1.000
N2—C1	1.332 (2)	C11—H111	1.000
N2—C8	1.470 (2)	C11—H112	1.000
O1—C15	1.421 (2)	C11—H113	1.000
O1—C16	1.444 (2)	C12—H121	1.000
Si1—C11	1.871 (2)	C12—H122	1.000
Si1—C12	1.872 (2)	C12—H123	1.000
Si1—C13	1.870 (2)	C13—H131	1.000
C1—C2	1.512 (2)	C13—H132	1.000
C2—C3	1.395 (3)	C13—H133	1.000
C2—C7	1.393 (3)	C14—C15	1.494 (3)
C3—C4	1.386 (3)	C14—H141	1.000
C3—H31	1.000	C14—H142	1.000
C4—C5	1.384 (3)	C14—H143	1.000
C4—H41	1.000	C15—H151	1.000
C5—C6	1.384 (3)	C15—H152	1.000
C5—H51	1.000	C16—C17	1.507 (3)
C6—C7	1.387 (3)	C16—H161	1.000
C6—H61	1.000	C16—H162	1.000
C7—H71	1.000	C17—H171	1.000
C8—C9	1.516 (3)	C17—H172	1.000
C8—H81	1.000	C17—H173	1.000

N1—Li1—N2	66.61 (11)	C10—C9—H91	108.79
N1—Li1—N2ⁱ	121.29 (16)	C8—C9—H92	108.7
N2—Li1—N2ⁱ	107.22 (14)	C10—C9—H92	108.80
N1—Li1—O1	123.08 (16)	H91—C9—H92	109.467
N2—Li1—O1	111.49 (16)	C9—C10—H101	110.21
N2ⁱ—Li1—O1	113.47 (15)	C9—C10—H102	109.10
Li1—N1—Si1	140.05 (12)	H101—C10—H102	109.476
Li1—N1—C1	85.59 (14)	C9—C10—H103	109.09
Si1—N1—C1	131.63 (13)	H101—C10—H103	109.476
Li1—N2—Li1ⁱ	72.78 (14)	H102—C10—H103	109.476
Li1—N2—C1	80.64 (13)	Si1—C11—H111	109.54
Li1ⁱ—N2—C1	127.44 (15)	Si1—C11—H112	109.21
Li1—N2—C8	141.30 (14)	H111—C11—H112	109.476
Li1ⁱ—N2—C8	108.94 (14)	Si1—C11—H113	109.65
C1—N2—C8	119.81 (15)	H111—C11—H113	109.476
Li1—O1—C15	134.78 (15)	H112—C11—H113	109.476
Li1—O1—C16	109.67 (14)	Si1—C12—H121	109.76
C15—O1—C16	112.43 (15)	Si1—C12—H122	109.22
N1—Si1—C11	111.66 (9)	H121—C12—H122	109.476
N1—Si1—C12	117.17 (9)	Si1—C12—H123	109.42
C11—Si1—C12	106.78 (11)	H121—C12—H123	109.476
N1—Si1—C13	105.94 (9)	H122—C12—H123	109.476
C11—Si1—C13	107.1 (1)	Si1—C13—H131	109.50
C12—Si1—C13	107.7 (1)	Si1—C13—H132	109.55
N1—C1—N2	118.71 (16)	H131—C13—H132	109.475
N1—C1—C2	119.68 (15)	Si1—C13—H133	109.36
N2—C1—C2	121.55 (15)	H131—C13—H133	109.476
C1—C2—C3	120.25 (16)	H132—C13—H133	109.476
C1—C2—C7	120.77 (16)	C15—C14—H141	110.17
C3—C2—C7	118.91 (17)	C15—C14—H142	108.86
C2—C3—C4	120.14 (19)	H141—C14—H142	109.476
C2—C3—H31	119.62	C15—C14—H143	109.37
C4—C3—H31	120.24	H141—C14—H143	109.476
C3—C4—C5	120.6 (2)	H142—C14—H143	109.476
C3—C4—H41	119.56	O1—C15—C14	109.84 (17)
C5—C4—H41	119.88	O1—C15—H151	109.45
C4—C5—C6	119.64 (18)	C14—C15—H151	109.64
C4—C5—H51	120.05	O1—C15—H152	109.28
C6—C5—H51	120.31	C14—C15—H152	109.14
C5—C6—C7	120.16 (19)	H151—C15—H152	109.467
C5—C6—H61	120.02	O1—C16—C17	112.18 (17)
C7—C6—H61	119.82	O1—C16—H161	108.7
C2—C7—C6	120.58 (9)	C17—C16—H161	108.63
C2—C7—H71	119.36	O1—C16—H162	109.0
C6—C7—H71	120.06	C17—C16—H162	108.87
N2—C8—C9	113.22 (15)	H161—C16—H162	109.467
N2—C8—H81	108.73	C16—C17—H171	109.97
C9—C8—H81	108.3	C16—C17—H172	109.33
N2—C8—H82	108.55	H171—C17—H172	109.476
C9—C8—H82	108.5	C16—C17—H173	109.09
H81—C8—H82	109.467	H171—C17—H173	109.476
C8—C9—C10	112.37 (17)	H172—C17—H173	109.476
C8—C9—H91	108.7

Symmetry code: (i) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Li₂(C₁₃H₂₂N₂Si)₂(C₄H₁₀O)₂]
M_r	628.94
Crystal system, space group	Triclinic, 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)
V (Å³)	969.2 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.32 × 0.28 × 0.28

Data collection
Diffractometer	Enraf-Nonius KappaCCD diffractometer
Absorption correction	Multi-scan DENZO (Otwinowski & Minor, 1997)
T_min, T_max	0.97, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	7923, 4372, 2907
R_int	0.02
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.042, 1.05
No. of reflections	4117
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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—N1	2.023 (3)	N1—Si1	1.7083 (15)
Li1—N2	2.145 (3)	N1—C1	1.330 (2)
Li1—N2ⁱ	2.073 (3)	N2—C1	1.332 (2)
Li1—O1	1.965 (3)	N2—C8	1.470 (2)
Li1—C1	2.334 (3)	C1—C2	1.512 (2)

N1—Li1—N2	66.61 (11)	Li1ⁱ—N2—C1	127.44 (15)
N1—Li1—N2ⁱ	121.29 (16)	Li1—N2—C8	141.30 (14)
N2—Li1—N2ⁱ	107.22 (14)	Li1ⁱ—N2—C8	108.94 (14)
N1—Li1—O1	123.08 (16)	C1—N2—C8	119.81 (15)
N2—Li1—O1	111.49 (16)	Li1—O1—C15	134.78 (15)
N2ⁱ—Li1—O1	113.47 (15)	Li1—O1—C16	109.67 (14)
Li1—N1—Si1	140.05 (12)	C15—O1—C16	112.43 (15)
Li1—N1—C1	85.59 (14)	N1—C1—N2	118.71 (16)
Si1—N1—C1	131.63 (13)	N1—C1—C2	119.68 (15)
Li1—N2—Li1ⁱ	72.78 (14)	N2—C1—C2	121.55 (15)
Li1—N2—C1	80.64 (13)

Symmetry code: (i) −x+1, −y+1, −z+2.

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