Bis[μ-2-(tri­methyl­silyl­amido)-6-(tri­methyl­silyl­amino)­pyridine-κ3N1,N2:N2]bis­[(diethyl ether-κO)lithium(I)]

Rave, J.A.; Garcia, D.A.; Hillesheim, P.C.; Guillet, G.L.

doi:10.1107/S2414314616007070

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160707

doi:10.1107/S2414314616007070

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Bis[μ-2-(trimethylsilylamido)-6-(trimethylsilylamino)pyridine-κ³N¹,N²:N²]bis[(diethyl ether-κO)lithium(I)]

Justin A. Rave,^a Diego A. Garcia,^a Patrick C. Hillesheim ^b and Gary L. Guillet ^a ^*

^aDepartment of Chemistry and Physics, Armstrong State University, Savannah, GA 31419, USA, and ^bDepartment of Chemistry, The University of Tennessee, Knoxville, TN 37996, USA
^*Correspondence e-mail: gary.guillet@armstrong.edu

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 1 February 2016; accepted 26 April 2016; online 4 May 2016)

The title complex, [Li₂(C₁₁H₂₂N₃Si₂)₂(C₄H₁₀O)₂], crystallizes in the P-1 space group with one molecule of a centrosymmetric dimeric complex in the unit cell. The lithium cation is coordinated in a bidentate fashion by the pyridyl N atom and a silylamido N atom of one 2,6-bis(trimethylsilylamido)pyridine ligand and by a monodentate, bridging silylamido N atom of another. A diethyl ether molecule completes the tetrahedral coordination environment for each lithium atom. Neither intra- nor intermolecular hydrogen bonding nor π–π stacking are observed in the crystal, likely indicating that weak electrostatic interactions are the dominant feature leading to the supramolecular structure.

Keywords: crystal structure; lithium complex; trialkylsilylaminopyridine.

CCDC reference: 1476698

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Chemical scheme

Structure description

The title complex (Fig. 1) represents the first dinuclear lithium cluster reported with the 2,6-bis(trimethylsilylamido)pyridine ligand. This ligand is known to support clusters of differing nuclearities including a related tetralithium complex containing tetrahydrofuran (THF) ligands (Glatz & Kempe, 2008a ), a hexalithium complex with benzonitrile ligands (Skvortsov et al., 2013 ), as well as a mononuclear complex (Rave et al., 2016 ). However, the ether-containing complex has not been investigated.

Figure 1
A view of the molecular structure of the title compound, omitting H atoms for clarity. Displacement ellipsoids are drawn at the 50% probability level. Only atoms in the asymmetric unit and symmetry-related N2′ atom are labelled (symmetry code for N2′: −x, 1 − y, 1 − z).

In the asymmetric unit, the lithium cation is coordinated by a bidentate 2,6-bis(trimethylsilylamido)pyridine ligand via the pyridiyl nitrogen (N1) with a bond length of 2.082 (5) Å and two bridging silylamido N atoms (N2 and N2′) with bond lengths of 2.098 (5) Å and 2.088 (5) Å, respectively. The related THF complex has Li—N distances that range from 2.054 Å to 2.178 Å, while in this structure they range from 2.082 Å to 2.098 Å. The Li—O bond distances are 1.931 and 1.915 (5) Å for the THF and the title ether complex, respectively. The 2,6-bis(trimethylsilylamido)pyridine ligand has been shown to support Co^II clusters (Glatz & Kempe, 2008b ) and Cu^I clusters (Glatz & Kempe, 2008c ), while two dinuclear chromium complexes with the triisopropyl congener have been reported (Huang et al., 2012 ), indicating this lithium complex may find utility as a synthon for transition metal clusters.

Synthesis and crystallization

2,6-bis(trimethylsilylamido)pyridine was synthesized according to a previous report (Danièle et al., 2001 ). The title complex was synthesized under an inert atmosphere by the addition of 4.27 mL of 2.45 M n-BuLi in cyclohexane (10.5 mmol) to 0.513 g of 2,6-diaminopyridine (4.70 mmol) in tetrahydrofuran at −30°C. The reaction was stirred overnight at room temperature. To the resulting slurry, chlorotrimethylsilane was added dropwise (1.02 g, 9.39 mmol) over a period of five minutes and the reaction was stirred for an additional 24 h. The reaction was filtered over a fritted filter to remove lithium chloride and the solvent was removed under reduced pressure yielding a yellow oil. Approximately 3 mL of hexanes was added to the residue and it was then filtered over celite to remove any residual lithium chloride. The solvent was again removed under reduced pressure. The residue was taken up in a small volume of diethyl ether and the solution was placed in a freezer at −30°C. Single crystals of the title complex formed over two days.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. The H atom bound to N3 is disordered over two sites, H3A and H3B, with occupancies 0.46 (6) and 0.54 (6). The two disordered H atoms were located as residual electron density peaks, and were refined freely. However, the N3—H3A and N3—H3B distances were restrained to be equal with a standard deviation of 0.02 Å.

Table 1
Experimental details

Crystal data
Chemical formula	[Li₂(C₁₁H₂₂N₃Si₂)₂(C₄H₁₀O)₂]
M_r	667.11
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	9.870 (7), 10.624 (8), 11.319 (7)
α, β, γ (°)	74.34 (2), 81.35 (2), 68.246 (19)
V (Å³)	1059.7 (13)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	0.17
Crystal size (mm)	0.3 × 0.27 × 0.22

Data collection
Diffractometer	Rigaku XtaLAB mini
Absorption correction	Multi-scan (REQAB; Rigaku, 1998 )
T_min, T_max	0.849, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11265, 4805, 2876
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.158, 1.03
No. of reflections	4805
No. of parameters	209
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.25
Computer programs: CrystalClear (Rigaku, 2009 ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1476698

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616007070/bh4003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616007070/bh4003Isup2.hkl

checkCIF report

Experimental top

2,6-bis(trimethylsilylamido)pyridine was synthesized according to a previous report (Danièle et al., 2001). The title complex was synthesized under an inert atmosphere by the addition of 4.27 ml of 2.45 M n-BuLi in cyclohexanes (10.5 mmol) to 0.513 g of 2,6-diaminopyridine (4.70 mmol) in tetrahydrofuran at -30°C. The reaction was stirred overnight at room temperature. To the resulting slurry, chlorotrimethylsilane was added dropwise (1.02 g, 9.39 mmol) over a period of five minutes and the reaction was stirred for an additional 24 h. The reaction was filtered over a fritted filter to remove lithium chloride and the solvent was removed under reduced pressure yielding a yellow oil. Approximately 3 mL of hexanes was added to the residue and it was then filtered over celite to remove any residual lithium chloride. The solvent was again removed under reduced pressure. The residue was taken up in a small volume of diethyl ether and the solution was placed in a freezer at -30°C. Single crystals of the title complex formed over two days.

Structure description top

The title complex (Fig. 1) represents the first dinuclear cluster with lithium reported with the 2,6-bis(trimethylsilylamido)pyridine ligand. This ligand is known to support clusters of differing nuclearities as a related tetralithium complex containing tetrahydrofuran (THF) ligands (Glatz & Kempe, 2008a), a hexalithium complex containing benzonitrile (Skvortsov et al., 2013), as well as a mononuclear complex (Rave et al., 2016) have all been previously observed. However, the ether complex has not been investigated.

In the asymmetric unit, the lithium cation is coordinated by a bidentate 2,6-bis(trimethylsilylamido)pyridine ligand via the pyridiyl nitrogen (N1) with a bond length of 2.082 (5) Å and two bridging silylamido N atoms (N2 and N2') with bond lengths of 2.098 (5) Å and 2.088 (5) Å, respectively. The related THF complex has Li—N distances that range from 2.054 Å to 2.178 Å, while in this structure they range from 2.082 Å to 2.098 Å. The Li—O bond distances are 1.931 and 1.915 (5) Å for the THF and the title ether complex, respectively. The 2,6-bis(trimethylsilylamido)pyridine ligand has been shown to support Co^II clusters (Glatz & Kempe, 2008b) and Cu^I clusters (Glatz & Kempe, 2008c), while two dinuclear chromium complexes with the triisopropyl congener have been reported (Huang et al., 2012), indicating this lithium complex may find utility as a synthon for transition metal clusters.

Computing details top

Data collection: CrystalClear (Rigaku, 2009); cell refinement: CrystalClear (Rigaku, 2009); data reduction: CrystalClear (Rigaku, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. A view of the molecular structure of the title compound, omitting H atoms for clarity. Displacement ellipsoids are drawn at the 50% probability level. Only atoms in the asymmetric unit and symmetry-related N2' atom are labelled (symmetry code for N2': -x, 1 - y, 1 - z). Carbon, lithium, nitrogen, oxygen, and silicon atoms shown as grey, cyan, blue, red, and orange ellipsoids, respectively.

Bis[µ-2-(trimethylsilylamido)-6-(trimethylsilylamino)pyridine-κ³N¹,N²:N²]bis[(diethyl ether-κO)lithium(I)] top

Crystal data top

[Li₂(C₁₁H₂₂N₃Si₂)₂(C₄H₁₀O)₂]	Z = 1
M_r = 667.11	F(000) = 364
Triclinic, P1	D_x = 1.045 Mg m⁻³
a = 9.870 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.624 (8) Å	Cell parameters from 2530 reflections
c = 11.319 (7) Å	θ = 2.1–27.5°
α = 74.34 (2)°	µ = 0.17 mm⁻¹
β = 81.35 (2)°	T = 173 K
γ = 68.246 (19)°	Prism, colourless
V = 1059.7 (13) Å³	0.3 × 0.27 × 0.22 mm

Data collection top

Rigaku XtaLAB mini diffractometer	4805 independent reflections
Radiation source: Sealed Tube	2876 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.056
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 2.2°
profile data from ω–scans	h = −12→12
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	k = −13→13
T_min = 0.849, T_max = 1.000	l = −14→14
11265 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: mixed
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0485P)² + 0.4277P] where P = (F_o² + 2F_c²)/3
4805 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Li₂(C₁₁H₂₂N₃Si₂)₂(C₄H₁₀O)₂]	γ = 68.246 (19)°
M_r = 667.11	V = 1059.7 (13) Å³
Triclinic, P1	Z = 1
a = 9.870 (7) Å	Mo Kα radiation
b = 10.624 (8) Å	µ = 0.17 mm⁻¹
c = 11.319 (7) Å	T = 173 K
α = 74.34 (2)°	0.3 × 0.27 × 0.22 mm
β = 81.35 (2)°

Data collection top

Rigaku XtaLAB mini diffractometer	4805 independent reflections
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	2876 reflections with I > 2σ(I)
T_min = 0.849, T_max = 1.000	R_int = 0.056
11265 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	1 restraint
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.31 e Å⁻³
4805 reflections	Δρ_min = −0.25 e Å⁻³
209 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Si1	0.19374 (10)	0.19834 (8)	0.62211 (7)	0.0376 (2)
Si2	0.31366 (9)	0.81456 (9)	0.10132 (7)	0.0383 (2)
N1	0.2124 (2)	0.5214 (2)	0.36674 (19)	0.0290 (5)
N2	0.1464 (2)	0.3537 (2)	0.5147 (2)	0.0306 (5)
N3	0.2656 (3)	0.7063 (3)	0.2323 (2)	0.0395 (6)
H3A	0.188 (4)	0.7368 (18)	0.2637 (18)	0.059*	0.46 (6)
H3B	0.2474 (11)	0.741 (2)	0.289 (3)	0.059*	0.54 (6)
O1	0.1403 (2)	0.6227 (2)	0.6407 (2)	0.0499 (6)
C1	0.2251 (3)	0.3830 (3)	0.4077 (2)	0.0295 (6)
C2	0.3140 (3)	0.2865 (3)	0.3370 (3)	0.0398 (7)
H2	0.3246	0.1907	0.3636	0.048*
C3	0.3847 (3)	0.3348 (3)	0.2288 (3)	0.0445 (8)
H3	0.4437	0.2712	0.1808	0.053*
C4	0.3711 (3)	0.4743 (3)	0.1891 (3)	0.0427 (7)
H4	0.4198	0.5071	0.1150	0.051*
C5	0.2837 (3)	0.5645 (3)	0.2617 (2)	0.0329 (6)
C6	0.3966 (4)	0.1089 (4)	0.6330 (3)	0.0642 (11)
H6A	0.4377	0.0691	0.5613	0.096*
H6B	0.4168	0.0343	0.7081	0.096*
H6C	0.4413	0.1766	0.6353	0.096*
C7	0.1174 (5)	0.0721 (4)	0.5936 (4)	0.0763 (13)
H7A	0.0132	0.1193	0.5789	0.114*
H7B	0.1298	−0.0063	0.6655	0.114*
H7C	0.1692	0.0376	0.5215	0.114*
C8	0.1201 (4)	0.2353 (3)	0.7762 (3)	0.0473 (8)
H8A	0.1724	0.2868	0.7991	0.071*
H8B	0.1334	0.1472	0.8376	0.071*
H8C	0.0157	0.2912	0.7726	0.071*
C9	0.5159 (4)	0.7672 (4)	0.0779 (3)	0.0566 (9)
H9A	0.5558	0.7663	0.1524	0.085*
H9B	0.5394	0.8357	0.0087	0.085*
H9C	0.5589	0.6745	0.0602	0.085*
C10	0.2377 (4)	0.8064 (4)	−0.0372 (3)	0.0568 (9)
H10A	0.2791	0.7111	−0.0491	0.085*
H10B	0.2631	0.8702	−0.1098	0.085*
H10C	0.1312	0.8336	−0.0252	0.085*
C11	0.2294 (4)	0.9911 (3)	0.1338 (3)	0.0595 (10)
H11A	0.1238	1.0126	0.1505	0.089*
H11B	0.2475	1.0604	0.0625	0.089*
H11C	0.2724	0.9930	0.2056	0.089*
C12	0.0508 (4)	0.7007 (3)	0.7268 (3)	0.0502 (8)
H12A	−0.0435	0.7623	0.6907	0.060*
H12B	0.0997	0.7605	0.7423	0.060*
C13	0.0218 (5)	0.6083 (4)	0.8471 (3)	0.0668 (11)
H13A	−0.0290	0.5506	0.8327	0.100*
H13B	−0.0392	0.6661	0.9030	0.100*
H13C	0.1147	0.5481	0.8840	0.100*
C14	0.2957 (4)	0.5744 (5)	0.6535 (4)	0.0722 (12)
H14A	0.3395	0.4776	0.6429	0.087*
H14B	0.3137	0.5735	0.7375	0.087*
C15	0.3672 (4)	0.6613 (5)	0.5643 (4)	0.0848 (14)
H15A	0.3400	0.6720	0.4814	0.127*
H15B	0.4734	0.6169	0.5688	0.127*
H15C	0.3362	0.7531	0.5830	0.127*
Li01	0.0751 (5)	0.5642 (5)	0.5205 (4)	0.0323 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0462 (5)	0.0251 (4)	0.0351 (5)	−0.0071 (4)	−0.0058 (4)	−0.0020 (3)
Si2	0.0425 (5)	0.0441 (5)	0.0297 (4)	−0.0232 (4)	0.0014 (3)	−0.0010 (3)
N1	0.0288 (12)	0.0289 (12)	0.0266 (11)	−0.0090 (10)	0.0015 (9)	−0.0052 (9)
N2	0.0292 (12)	0.0262 (11)	0.0327 (12)	−0.0082 (10)	0.0026 (9)	−0.0054 (9)
N3	0.0454 (16)	0.0401 (14)	0.0325 (14)	−0.0194 (12)	0.0085 (11)	−0.0073 (11)
O1	0.0404 (13)	0.0712 (16)	0.0445 (13)	−0.0194 (12)	−0.0006 (10)	−0.0247 (11)
C1	0.0275 (14)	0.0297 (14)	0.0313 (14)	−0.0101 (12)	−0.0048 (11)	−0.0051 (11)
C2	0.0427 (18)	0.0325 (15)	0.0419 (17)	−0.0082 (14)	−0.0003 (13)	−0.0129 (13)
C3	0.0457 (19)	0.0435 (18)	0.0420 (18)	−0.0111 (15)	0.0069 (14)	−0.0174 (14)
C4	0.0483 (19)	0.0456 (18)	0.0308 (16)	−0.0165 (15)	0.0085 (13)	−0.0090 (13)
C5	0.0338 (15)	0.0353 (15)	0.0301 (15)	−0.0139 (13)	0.0008 (12)	−0.0071 (12)
C6	0.055 (2)	0.057 (2)	0.051 (2)	0.0174 (18)	−0.0075 (17)	−0.0142 (17)
C7	0.128 (4)	0.046 (2)	0.061 (3)	−0.044 (2)	−0.021 (2)	0.0045 (18)
C8	0.0471 (19)	0.0438 (18)	0.0389 (18)	−0.0091 (16)	−0.0033 (14)	0.0004 (14)
C9	0.051 (2)	0.084 (3)	0.046 (2)	−0.039 (2)	0.0071 (16)	−0.0165 (18)
C10	0.058 (2)	0.068 (2)	0.0427 (19)	−0.0237 (19)	−0.0082 (16)	−0.0055 (17)
C11	0.075 (3)	0.0451 (19)	0.054 (2)	−0.0274 (19)	0.0074 (18)	−0.0002 (16)
C12	0.072 (2)	0.0484 (19)	0.0408 (18)	−0.0289 (18)	0.0018 (16)	−0.0183 (15)
C13	0.087 (3)	0.058 (2)	0.053 (2)	−0.032 (2)	0.012 (2)	−0.0085 (18)
C14	0.052 (2)	0.088 (3)	0.072 (3)	−0.029 (2)	−0.023 (2)	0.006 (2)
C15	0.055 (2)	0.129 (4)	0.074 (3)	−0.046 (3)	−0.009 (2)	−0.007 (3)
Li01	0.033 (3)	0.031 (2)	0.030 (2)	−0.009 (2)	−0.0003 (19)	−0.0059 (19)

Geometric parameters (Å, º) top

Si1—N2	1.713 (2)	C7—H7A	0.9800
Si1—C6	1.878 (4)	C7—H7B	0.9800
Si1—C7	1.878 (4)	C7—H7C	0.9800
Si1—C8	1.871 (3)	C8—H8A	0.9800
Si1—Li01ⁱ	3.184 (5)	C8—H8B	0.9800
Si2—N3	1.737 (3)	C8—H8C	0.9800
Si2—C9	1.865 (4)	C9—H9A	0.9800
Si2—C10	1.871 (4)	C9—H9B	0.9800
Si2—C11	1.862 (4)	C9—H9C	0.9800
N1—C1	1.381 (3)	C10—H10A	0.9800
N1—C5	1.346 (3)	C10—H10B	0.9800
N1—Li01	2.082 (5)	C10—H10C	0.9800
N2—C1	1.364 (3)	C11—H11A	0.9800
N2—Li01ⁱ	2.088 (5)	C11—H11B	0.9800
N2—Li01	2.098 (5)	C11—H11C	0.9800
N3—H3A	0.79 (4)	C12—H12A	0.9900
N3—H3B	0.79 (4)	C12—H12B	0.9900
N3—C5	1.400 (4)	C12—C13	1.506 (5)
O1—C12	1.432 (4)	C13—H13A	0.9800
O1—C14	1.442 (4)	C13—H13B	0.9800
O1—Li01	1.915 (5)	C13—H13C	0.9800
C1—C2	1.423 (4)	C14—H14A	0.9900
C2—H2	0.9500	C14—H14B	0.9900
C2—C3	1.386 (4)	C14—C15	1.460 (5)
C3—H3	0.9500	C15—H15A	0.9800
C3—C4	1.389 (4)	C15—H15B	0.9800
C4—H4	0.9500	C15—H15C	0.9800
C4—C5	1.392 (4)	Li01—Si1ⁱ	3.184 (5)
C6—H6A	0.9800	Li01—N2ⁱ	2.088 (5)
C6—H6B	0.9800	Li01—Li01ⁱ	2.515 (9)
C6—H6C	0.9800

N2—Si1—C6	113.31 (15)	Si1—C8—H8C	109.5
N2—Si1—C7	112.67 (16)	H8A—C8—H8B	109.5
N2—Si1—C8	107.94 (13)	H8A—C8—H8C	109.5
N2—Si1—Li01ⁱ	36.99 (11)	H8B—C8—H8C	109.5
C6—Si1—Li01ⁱ	149.26 (15)	Si2—C9—H9A	109.5
C7—Si1—C6	107.8 (2)	Si2—C9—H9B	109.5
C7—Si1—Li01ⁱ	85.89 (17)	Si2—C9—H9C	109.5
C8—Si1—C6	106.35 (16)	H9A—C9—H9B	109.5
C8—Si1—C7	108.53 (18)	H9A—C9—H9C	109.5
C8—Si1—Li01ⁱ	94.47 (14)	H9B—C9—H9C	109.5
N3—Si2—C9	111.36 (15)	Si2—C10—H10A	109.5
N3—Si2—C10	110.46 (16)	Si2—C10—H10B	109.5
N3—Si2—C11	103.72 (15)	Si2—C10—H10C	109.5
C9—Si2—C10	109.81 (16)	H10A—C10—H10B	109.5
C11—Si2—C9	110.23 (17)	H10A—C10—H10C	109.5
C11—Si2—C10	111.15 (18)	H10B—C10—H10C	109.5
C1—N1—Li01	89.4 (2)	Si2—C11—H11A	109.5
C5—N1—C1	120.5 (2)	Si2—C11—H11B	109.5
C5—N1—Li01	150.2 (2)	Si2—C11—H11C	109.5
Si1—N2—Li01	134.99 (18)	H11A—C11—H11B	109.5
Si1—N2—Li01ⁱ	113.43 (17)	H11A—C11—H11C	109.5
C1—N2—Si1	125.15 (19)	H11B—C11—H11C	109.5
C1—N2—Li01ⁱ	108.7 (2)	O1—C12—H12A	109.1
C1—N2—Li01	89.1 (2)	O1—C12—H12B	109.1
Li01ⁱ—N2—Li01	73.8 (2)	O1—C12—C13	112.5 (3)
Si2—N3—H3A	116.7	H12A—C12—H12B	107.8
Si2—N3—H3B	110.6	C13—C12—H12A	109.1
C5—N3—Si2	132.4 (2)	C13—C12—H12B	109.1
C5—N3—H3A	100.6	C12—C13—H13A	109.5
C5—N3—H3B	115.2	C12—C13—H13B	109.5
C12—O1—C14	115.8 (3)	C12—C13—H13C	109.5
C12—O1—Li01	126.9 (2)	H13A—C13—H13B	109.5
C14—O1—Li01	117.1 (3)	H13A—C13—H13C	109.5
N1—C1—C2	119.1 (2)	H13B—C13—H13C	109.5
N2—C1—N1	114.5 (2)	O1—C14—H14A	109.1
N2—C1—C2	126.4 (3)	O1—C14—H14B	109.1
C1—C2—H2	120.6	O1—C14—C15	112.7 (3)
C3—C2—C1	118.8 (3)	H14A—C14—H14B	107.8
C3—C2—H2	120.6	C15—C14—H14A	109.1
C2—C3—H3	119.3	C15—C14—H14B	109.1
C2—C3—C4	121.3 (3)	C14—C15—H15A	109.5
C4—C3—H3	119.3	C14—C15—H15B	109.5
C3—C4—H4	121.1	C14—C15—H15C	109.5
C3—C4—C5	117.8 (3)	H15A—C15—H15B	109.5
C5—C4—H4	121.1	H15A—C15—H15C	109.5
N1—C5—N3	115.0 (2)	H15B—C15—H15C	109.5
N1—C5—C4	122.5 (3)	N1—Li01—Si1ⁱ	97.29 (17)
C4—C5—N3	122.5 (3)	N1—Li01—N2	67.04 (16)
Si1—C6—H6A	109.5	N1—Li01—N2ⁱ	113.4 (2)
Si1—C6—H6B	109.5	N1—Li01—Li01ⁱ	90.3 (3)
Si1—C6—H6C	109.5	N2—Li01—Si1ⁱ	124.2 (2)
H6A—C6—H6B	109.5	N2ⁱ—Li01—Si1ⁱ	29.58 (9)
H6A—C6—H6C	109.5	N2ⁱ—Li01—N2	106.2 (2)
H6B—C6—H6C	109.5	N2ⁱ—Li01—Li01ⁱ	53.26 (18)
Si1—C7—H7A	109.5	N2—Li01—Li01ⁱ	52.89 (18)
Si1—C7—H7B	109.5	O1—Li01—Si1ⁱ	113.1 (2)
Si1—C7—H7C	109.5	O1—Li01—N1	118.9 (2)
H7A—C7—H7B	109.5	O1—Li01—N2	121.4 (2)
H7A—C7—H7C	109.5	O1—Li01—N2ⁱ	118.9 (2)
H7B—C7—H7C	109.5	O1—Li01—Li01ⁱ	146.7 (3)
Si1—C8—H8A	109.5	Li01ⁱ—Li01—Si1ⁱ	75.4 (2)
Si1—C8—H8B	109.5

Si1—N2—C1—N1	−149.7 (2)	C8—Si1—N2—C1	150.0 (2)
Si1—N2—C1—C2	31.2 (4)	C8—Si1—N2—Li01ⁱ	−72.9 (2)
Si2—N3—C5—N1	−170.6 (2)	C8—Si1—N2—Li01	17.3 (3)
Si2—N3—C5—C4	10.6 (5)	C9—Si2—N3—C5	−67.9 (3)
N1—C1—C2—C3	−0.3 (4)	C10—Si2—N3—C5	54.4 (3)
N2—C1—C2—C3	178.8 (3)	C11—Si2—N3—C5	173.6 (3)
C1—N1—C5—N3	−178.1 (2)	C12—O1—C14—C15	−100.7 (4)
C1—N1—C5—C4	0.7 (4)	C14—O1—C12—C13	−83.7 (4)
C1—C2—C3—C4	0.5 (5)	Li01ⁱ—Si1—N2—C1	−137.1 (3)
C2—C3—C4—C5	−0.1 (5)	Li01ⁱ—Si1—N2—Li01	90.3 (3)
C3—C4—C5—N1	−0.5 (4)	Li01—N1—C1—N2	1.0 (3)
C3—C4—C5—N3	178.2 (3)	Li01—N1—C1—C2	−179.8 (3)
C5—N1—C1—N2	−179.5 (2)	Li01—N1—C5—N3	0.8 (6)
C5—N1—C1—C2	−0.3 (4)	Li01—N1—C5—C4	179.7 (4)
C6—Si1—N2—C1	32.5 (3)	Li01ⁱ—N2—C1—N1	71.6 (3)
C6—Si1—N2—Li01	−100.2 (3)	Li01—N2—C1—N1	−1.0 (3)
C6—Si1—N2—Li01ⁱ	169.6 (2)	Li01ⁱ—N2—C1—C2	−107.5 (3)
C7—Si1—N2—C1	−90.2 (3)	Li01—N2—C1—C2	179.9 (3)
C7—Si1—N2—Li01ⁱ	46.9 (2)	Li01—O1—C12—C13	91.0 (4)
C7—Si1—N2—Li01	137.1 (3)	Li01—O1—C14—C15	84.1 (4)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Li₂(C₁₁H₂₂N₃Si₂)₂(C₄H₁₀O)₂]
M_r	667.11
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.870 (7), 10.624 (8), 11.319 (7)
α, β, γ (°)	74.34 (2), 81.35 (2), 68.246 (19)
V (Å³)	1059.7 (13)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.3 × 0.27 × 0.22

Data collection
Diffractometer	Rigaku XtaLAB mini
Absorption correction	Multi-scan (REQAB; Rigaku, 1998)
T_min, T_max	0.849, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11265, 4805, 2876
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.158, 1.03
No. of reflections	4805
No. of parameters	209
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.25

Computer programs: CrystalClear (Rigaku, 2009), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

The authors would like to thank Armstrong State University for funding.

References

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