Bis[μ-N-(tert-butyl­dimethyl­sil­yl)quinolin-8-aminato-1:2κ2N1,N8:N8](N,N,N′,N′-tetra­methyl­ethane-1,2-diamine-1κ2N,N′)lithiumsodium

Chen, J.; Yuan, L.

doi:10.1107/S160053681204576X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1474

doi:10.1107/S160053681204576X

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Bis[μ-N-(tert-butyldimethylsilyl)quinolin-8-aminato-1:2κ²N¹,N⁸:N⁸](N,N,N′,N′-tetramethylethane-1,2-diamine-1κ²N,N′)lithiumsodium

Juan Chen ^a ^* and Li Yuan ^b

^aDepartment of Chemistry, Taiyuan Teachers College, Taiyuan 030031, People's Republic of China, and ^bTechnical Center of Shanxi Entry–Exit Inspection and Quarantine Bureau, No. 8 Yifen Strteet, Taiyuan 030024, People's Republic of China
^*Correspondence e-mail: sdbai@sxu.edu.cn

(Received 28 October 2012; accepted 6 November 2012; online 14 November 2012)

In the heterometallic title bulky amido complex, [LiNa(C₁₅H₂₁N₂Si)₂(C₆H₁₆N₂)], both alkali metal ions are four-coordinated with distorted tetrahedral geometries. The Li⁺ ion is N,N′-chelated by the N-silylated amido ligand, with Li—N = 2.015 (5) and 2.074 (5) Å. The two amido ligands are arranged cis to each other. The molecule exhibits a twofold rotational symmetry operation along the Li–Na axis. The Na⁺ ion is coordinated by two N atoms from the tetramethylethylenediamine ligand [Na—N = 2.553 (4) Å] and shares two amido N atoms from the N-silylated amido ligands with the Li⁺ ion. Although the crystal structure contains voids with an approximate volume of 50 Å³ there is no inclusion of solvent molecules.

Related literature

For related metal complexes with N-silylated quinolyl amido ligands, see: Engelhardt et al. (1988 , 1990 , 1991 ). For silyl-bridged aminoquinoline derivatives, see: Jones et al. (2000 ). For mixed alkali metal systems as superbase reagents, see: Forbes et al. (2003 ); Mulvey (2006 ); Wei et al. (2008 ).

Experimental

Crystal data

[LiNa(C₁₅H₂₁N₂Si)₂(C₆H₁₆N₂)]
M_r = 660.99
Monoclinic, C 2/c
a = 12.653 (2) Å
b = 18.542 (3) Å
c = 18.296 (3) Å
β = 108.794 (3)°
V = 4063.6 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.962, T_max = 0.975
11843 measured reflections
4001 independent reflections
2128 reflections with I > 2σ(I)
R_int = 0.071

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.195
S = 0.97
4001 reflections
209 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681204576X/rk2385sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204576X/rk2385Isup2.hkl

checkCIF report

Comment top

8–aminoquinoline is a good chelate amido ligand precursor. It could yield a tetranuclear lithium complex after reacting with n–LiBu in Et₂O. The product has a centrosymmetric dimeric structure with a Li₄N₄ step–ladder arrangement (Jones et al., 2000). The silylated aminoquinoline, HN(8–C₉H₆N)(SiMe₃), is a bulky ligand and it has proven to be suitable to coordinate to Li, Mg, Zn and Al ions (Engelhardt et al., 1988; 1990; 1991). The corresponding lithium complexes exist in either monomeric or dimeric form. The silyl–bridged aminoquinoline turn into a tetradentate ligand and its lithium derivative is tetranuclear (Jones et al., 2000).

The research involving mixed organo–alkali metal amides is vivid as they could serve as superbase reagents and have interesting structures (Forbes et al., 2003; Mulvey, 2006; Wei et al., 2008). Based on the above work, we employed the bulky more demanding aminoquinoline analogue [HN(8–C₉H₆N)(SiBu^tMe₂)] to prepare a Li/Na hetero alkali metal amide. Its crystal structure is described here.

The title compound was prepared by metallation of the amine with half an equivalent of n–butyl lithium and half an equivalent of butyl sodium. Neutral donor TMEDA was added into the mixture and the red crystalline product was grown from hexane.

In the molecule of title compound, the lithium ion is fixed by two equivalents of the chelating quinolyl amido ligand, the corresponding bite angle N_amido–Li–N_quinolyl being 84.77 (12)°. The observed Li–N_amido bond distance of 2.074 (5)Å is marginally different from reported values in literature and slightly longer than the Li–N_quinolyl bond (2.015 (5)Å). It results a distorted tetrahedral configuration around the lithium ion. The sodium atom is connected by the amido nitrogen atoms and it is bound to the neutral donor TMEDA simultaneously, which also leads to a distorted tetrahedral geometry. The molecule exhibits a C₂ rotational symmetrical operation along the axis crossing Li and Na atoms. It makes the [Li–N_amido–Na–N_amido] cyclic ring to be planar. The two metal atoms are separated by the distance of 2.951 (7)Å.

Related literature top

For related metal complexes with N-silylated quinolyl amido ligands, see: Engelhardt et al. (1988, 1990, 1991). For silyl-bridged aminoquinoline derivatives, see: Jones et al. (2000). For mixed alkali metal systems as superbase reagents, see: Forbes et al. (2003); Mulvey (2006); Wei et al. (2008).

Experimental top

A solution of 8–tert–butyldimethylsilylaminoquinoline (0.71 g, 2.73 mmol) in Et₂O (ca 20 ml) was added into the mixture of n–LiBu (1.6 M, 0.86 ml, 1.37 mmol) and n–NaBu (0.11 g, 1.37 mmol) in Et₂O (ca 20 ml) at 195 K. Then TMEDA (0.16 g, 1.37 mmol) was added and the resulting mixture was kept stirring overnight. The red solution was concentrated and the residue was recrystallized with hexane to give the title compound as red crystals (yield 0.35 g, 39%). ¹H NMR (300 MHz, C₆D₆): δ = 8.588 - 6.735 (m, 12H; quinoline ring), 1.906, 1.840 (d, 16H; TMEDA), 1.326, 1.028 (d, 18H; t–butyl), 0.497, 0.277 (d, 12H; methyls on silyl); ¹³C NMR (75 MHz, C₆D₆): δ = 147.452, 137.652, 136.399, 121.771, 115.578, 110.415 (CH of quinoline ring), 57.652, 46.140 TMEDA, 29.237, 26.889 (methyl of t–butyl), 18.664, 15.921 (ipso–C of t–butyl), -0.242, -4.122 (methyls on silyl). Anal. Calc. for C₃₆H₅₈LiN₆NaSi₂: C, 65.42; H, 8.84; N, 12.71%. Found: C, 65.10; H, 8.81; N, 12.69%.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure, showing the atom–numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius. Symmetry code: (i) -x+2, y, -z+1/2.

Bis[µ-N-(tert-butyldimethylsilyl)quinolin-8-aminato- 1:2κ²N¹,N⁸:N⁸](N,N,N', N'-tetramethylethane-1,2-diamine-1κ²N,N')lithiumsodium top

Crystal data top

[LiNa(C₁₅H₂₁N₂Si)₂(C₆H₁₆N₂)]	F(000) = 1432
M_r = 660.99	D_x = 1.080 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3078 reflections
a = 12.653 (2) Å	θ = 2.2–25.5°
b = 18.542 (3) Å	µ = 0.13 mm⁻¹
c = 18.296 (3) Å	T = 295 K
β = 108.794 (3)°	Block, red
V = 4063.6 (11) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4001 independent reflections
Radiation source: fine-focus sealed tube	2128 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→15
T_min = 0.962, T_max = 0.975	k = −22→22
11843 measured reflections	l = −22→22

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.195	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.1027P)²] where P = (F_o² + 2F_c²)/3
4001 reflections	(Δ/σ)_max = 0.011
209 parameters	Δρ_max = 0.32 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

[LiNa(C₁₅H₂₁N₂Si)₂(C₆H₁₆N₂)]	V = 4063.6 (11) Å³
M_r = 660.99	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 12.653 (2) Å	µ = 0.13 mm⁻¹
b = 18.542 (3) Å	T = 295 K
c = 18.296 (3) Å	0.30 × 0.25 × 0.20 mm
β = 108.794 (3)°

Data collection top

Bruker SMART CCD diffractometer	4001 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2128 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.975	R_int = 0.071
11843 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	1 restraint
wR(F²) = 0.195	H-atom parameters constrained
S = 0.97	Δρ_max = 0.32 e Å⁻³
4001 reflections	Δρ_min = −0.26 e Å⁻³
209 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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

	x	y	z	U_iso*/U_eq
Si1	0.79825 (8)	0.03304 (5)	0.11244 (5)	0.0488 (3)
Na1	1.0000	−0.04676 (9)	0.2500	0.0575 (5)
Li1	1.0000	0.1121 (4)	0.2500	0.0521 (19)
N1	0.9134 (3)	0.16649 (16)	0.30734 (17)	0.0624 (8)
N2	0.8563 (2)	0.05043 (13)	0.20820 (14)	0.0464 (7)
N3	1.0507 (4)	−0.15746 (18)	0.1852 (2)	0.0823 (11)
C1	0.9395 (4)	0.2245 (2)	0.3513 (2)	0.0823 (13)
H1A	0.9985	0.2530	0.3483	0.099*
C2	0.8829 (5)	0.2453 (3)	0.4023 (3)	0.110 (2)
H2A	0.9042	0.2862	0.4329	0.132*
C3	0.7970 (5)	0.2042 (4)	0.4057 (3)	0.108 (2)
H3A	0.7591	0.2170	0.4397	0.130*
C4	0.7628 (4)	0.1428 (3)	0.3595 (2)	0.0729 (12)
C5	0.6742 (4)	0.1006 (4)	0.3607 (3)	0.1021 (18)
H5	0.6337	0.1117	0.3936	0.122*
C6	0.6462 (4)	0.0414 (3)	0.3125 (3)	0.0976 (17)
H6	0.5867	0.0124	0.3134	0.117*
C7	0.7050 (3)	0.0245 (2)	0.2627 (2)	0.0748 (12)
H7	0.6828	−0.0158	0.2311	0.090*
C8	0.7963 (3)	0.06445 (18)	0.25710 (18)	0.0504 (8)
C9	0.8254 (3)	0.1260 (2)	0.30898 (18)	0.0545 (9)
C10	0.9163 (3)	0.0301 (2)	0.0717 (2)	0.0705 (11)
H10A	0.8932	0.0517	0.0214	0.106*
H10B	0.9374	−0.0192	0.0679	0.106*
H10C	0.9789	0.0561	0.1050	0.106*
C11	0.7207 (4)	−0.05573 (19)	0.0867 (2)	0.0783 (13)
H11A	0.6527	−0.0483	0.0447	0.117*
H11B	0.7035	−0.0738	0.1307	0.117*
H11C	0.7666	−0.0900	0.0715	0.117*
C12	0.6967 (3)	0.10601 (18)	0.05847 (19)	0.0565 (9)
C13	0.7530 (4)	0.1797 (2)	0.0801 (3)	0.0890 (14)
H13A	0.7026	0.2170	0.0534	0.134*
H13B	0.8195	0.1814	0.0657	0.134*
H13C	0.7721	0.1869	0.1348	0.134*
C14	0.5904 (3)	0.1066 (2)	0.0806 (2)	0.0827 (13)
H14A	0.5416	0.1439	0.0525	0.124*
H14B	0.6091	0.1154	0.1350	0.124*
H14C	0.5537	0.0607	0.0683	0.124*
C15	0.6644 (4)	0.0951 (3)	−0.0291 (2)	0.0963 (16)
H15A	0.6132	0.1323	−0.0551	0.144*
H15B	0.6295	0.0489	−0.0426	0.144*
H15C	0.7301	0.0974	−0.0443	0.144*
C16	1.1708 (6)	−0.1574 (4)	0.2048 (4)	0.154 (3)
H16A	1.1936	−0.1983	0.1814	0.231*
H16B	1.2042	−0.1601	0.2598	0.231*
H16C	1.1942	−0.1139	0.1861	0.231*
C17	1.0020 (6)	−0.1651 (3)	0.1025 (3)	0.142 (3)
H17A	1.0289	−0.2087	0.0862	0.213*
H17B	1.0226	−0.1246	0.0774	0.213*
H17C	0.9222	−0.1673	0.0889	0.213*
C18	1.0183 (8)	−0.2176 (3)	0.2183 (4)	0.168 (3)
H18A	0.9594	−0.2404	0.1771	0.201*
H18B	1.0813	−0.2504	0.2310	0.201*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0479 (6)	0.0477 (5)	0.0494 (5)	0.0042 (4)	0.0139 (4)	−0.0013 (4)
Na1	0.0601 (12)	0.0466 (10)	0.0622 (11)	0.000	0.0148 (10)	0.000
Li1	0.046 (5)	0.046 (4)	0.067 (5)	0.000	0.022 (4)	0.000
N1	0.057 (2)	0.0589 (18)	0.0668 (19)	0.0077 (16)	0.0129 (16)	−0.0110 (15)
N2	0.0419 (15)	0.0502 (15)	0.0484 (15)	0.0008 (12)	0.0166 (13)	−0.0002 (12)
N3	0.104 (3)	0.056 (2)	0.085 (3)	0.005 (2)	0.028 (2)	−0.0130 (17)
C1	0.078 (3)	0.071 (3)	0.088 (3)	0.015 (2)	0.011 (3)	−0.025 (2)
C2	0.102 (4)	0.113 (4)	0.090 (4)	0.046 (4)	−0.004 (4)	−0.044 (3)
C3	0.092 (4)	0.171 (6)	0.051 (3)	0.068 (4)	0.008 (3)	−0.022 (3)
C4	0.055 (3)	0.123 (4)	0.039 (2)	0.033 (3)	0.0122 (19)	0.005 (2)
C5	0.069 (3)	0.193 (6)	0.049 (3)	0.034 (4)	0.027 (3)	0.023 (3)
C6	0.052 (3)	0.178 (5)	0.067 (3)	0.001 (3)	0.025 (2)	0.046 (3)
C7	0.057 (2)	0.106 (3)	0.058 (2)	−0.011 (2)	0.015 (2)	0.017 (2)
C8	0.0383 (19)	0.065 (2)	0.0451 (18)	0.0073 (16)	0.0099 (16)	0.0119 (16)
C9	0.044 (2)	0.073 (2)	0.0430 (18)	0.0215 (18)	0.0091 (17)	0.0048 (16)
C10	0.065 (3)	0.086 (3)	0.062 (2)	0.014 (2)	0.024 (2)	−0.0095 (19)
C11	0.092 (3)	0.061 (2)	0.069 (2)	−0.003 (2)	0.008 (2)	−0.0072 (19)
C12	0.057 (2)	0.061 (2)	0.051 (2)	0.0083 (18)	0.0166 (18)	0.0067 (16)
C13	0.093 (3)	0.059 (2)	0.113 (3)	0.014 (2)	0.030 (3)	0.020 (2)
C14	0.061 (3)	0.101 (3)	0.083 (3)	0.023 (2)	0.019 (2)	0.021 (2)
C15	0.105 (4)	0.119 (4)	0.054 (2)	0.037 (3)	0.012 (3)	0.014 (2)
C16	0.114 (5)	0.159 (6)	0.172 (6)	0.003 (5)	0.023 (5)	−0.084 (5)
C17	0.183 (7)	0.135 (5)	0.087 (4)	0.072 (5)	0.015 (4)	−0.026 (3)
C18	0.278 (10)	0.063 (3)	0.199 (8)	0.010 (5)	0.127 (7)	−0.021 (4)

Geometric parameters (Å, º) top

Si1—N2	1.698 (3)	C5—H5	0.9300
Si1—C10	1.873 (4)	C6—C7	1.386 (6)
Si1—C11	1.896 (4)	C6—H6	0.9300
Si1—C12	1.908 (3)	C7—C8	1.403 (5)
Si1—Na1	3.3014 (12)	C7—H7	0.9300
Na1—N2ⁱ	2.498 (3)	C8—C9	1.454 (5)
Na1—N2	2.498 (3)	C10—H10A	0.9600
Na1—N3	2.553 (4)	C10—H10B	0.9600
Na1—N3ⁱ	2.553 (4)	C10—H10C	0.9600
Na1—Li1	2.946 (7)	C11—H11A	0.9600
Na1—Si1ⁱ	3.3014 (12)	C11—H11B	0.9600
Li1—N1ⁱ	2.015 (5)	C11—H11C	0.9600
Li1—N1	2.015 (5)	C12—C14	1.524 (5)
Li1—N2	2.074 (5)	C12—C15	1.533 (5)
Li1—N2ⁱ	2.074 (5)	C12—C13	1.533 (5)
Li1—C9ⁱ	2.765 (4)	C13—H13A	0.9600
Li1—C9	2.765 (4)	C13—H13B	0.9600
Li1—C8	2.768 (4)	C13—H13C	0.9600
Li1—C8ⁱ	2.768 (4)	C14—H14A	0.9600
N1—C1	1.321 (4)	C14—H14B	0.9600
N1—C9	1.351 (5)	C14—H14C	0.9600
N2—C8	1.373 (4)	C15—H15A	0.9600
N3—C18	1.392 (6)	C15—H15B	0.9600
N3—C16	1.444 (7)	C15—H15C	0.9600
N3—C17	1.446 (5)	C16—H16A	0.9600
C1—C2	1.400 (7)	C16—H16B	0.9600
C1—H1A	0.9300	C16—H16C	0.9600
C2—C3	1.345 (8)	C17—H17A	0.9600
C2—H2A	0.9300	C17—H17B	0.9600
C3—C4	1.401 (7)	C17—H17C	0.9600
C3—H3A	0.9300	C18—C18ⁱ	1.379 (10)
C4—C5	1.373 (7)	C18—H18A	0.9700
C4—C9	1.432 (5)	C18—H18B	0.9700
C5—C6	1.381 (7)

N2—Si1—C10	106.28 (15)	C3—C2—C1	118.0 (5)
N2—Si1—C11	116.03 (15)	C3—C2—H2A	121.0
C10—Si1—C11	106.90 (18)	C1—C2—H2A	121.0
N2—Si1—C12	113.25 (14)	C2—C3—C4	121.9 (5)
C10—Si1—C12	107.79 (17)	C2—C3—H3A	119.0
C11—Si1—C12	106.18 (17)	C4—C3—H3A	119.0
N2—Si1—Na1	47.72 (9)	C5—C4—C3	123.3 (5)
C10—Si1—Na1	76.71 (12)	C5—C4—C9	120.7 (4)
C11—Si1—Na1	90.67 (12)	C3—C4—C9	116.0 (5)
C12—Si1—Na1	159.86 (11)	C4—C5—C6	119.0 (4)
N2ⁱ—Na1—N2	87.66 (13)	C4—C5—H5	120.5
N2ⁱ—Na1—N3	117.08 (11)	C6—C5—H5	120.5
N2—Na1—N3	134.80 (10)	C5—C6—C7	121.3 (5)
N2ⁱ—Na1—N3ⁱ	134.80 (10)	C5—C6—H6	119.4
N2—Na1—N3ⁱ	117.08 (11)	C7—C6—H6	119.4
N3—Na1—N3ⁱ	72.99 (19)	C6—C7—C8	123.8 (4)
N2ⁱ—Na1—Li1	43.83 (6)	C6—C7—H7	118.1
N2—Na1—Li1	43.83 (6)	C8—C7—H7	118.1
N3—Na1—Li1	143.51 (9)	N2—C8—C7	126.1 (3)
N3ⁱ—Na1—Li1	143.51 (9)	N2—C8—C9	119.8 (3)
N2ⁱ—Na1—Si1ⁱ	30.20 (6)	C7—C8—C9	114.1 (3)
N2—Na1—Si1ⁱ	102.57 (8)	N2—C8—Li1	46.37 (17)
N3—Na1—Si1ⁱ	117.78 (10)	C7—C8—Li1	166.6 (3)
N3ⁱ—Na1—Si1ⁱ	104.74 (9)	C9—C8—Li1	74.7 (2)
Li1—Na1—Si1ⁱ	63.38 (3)	N1—C9—C4	121.6 (4)
N2ⁱ—Na1—Si1	102.57 (8)	N1—C9—C8	117.3 (3)
N2—Na1—Si1	30.20 (6)	C4—C9—C8	121.0 (4)
N3—Na1—Si1	104.74 (9)	N1—C9—Li1	43.6 (2)
N3ⁱ—Na1—Si1	117.78 (10)	C4—C9—Li1	161.7 (3)
Li1—Na1—Si1	63.38 (3)	C8—C9—Li1	74.8 (2)
Si1ⁱ—Na1—Si1	126.75 (6)	Si1—C10—H10A	109.5
N1ⁱ—Li1—N1	119.9 (4)	Si1—C10—H10B	109.5
N1ⁱ—Li1—N2	130.03 (11)	H10A—C10—H10B	109.5
N1—Li1—N2	84.77 (12)	Si1—C10—H10C	109.5
N1ⁱ—Li1—N2ⁱ	84.77 (12)	H10A—C10—H10C	109.5
N1—Li1—N2ⁱ	130.03 (11)	H10B—C10—H10C	109.5
N2—Li1—N2ⁱ	113.1 (4)	Si1—C11—H11A	109.5
N1ⁱ—Li1—C9ⁱ	27.53 (11)	Si1—C11—H11B	109.5
N1—Li1—C9ⁱ	142.5 (3)	H11A—C11—H11B	109.5
N2—Li1—C9ⁱ	128.53 (19)	Si1—C11—H11C	109.5
N2ⁱ—Li1—C9ⁱ	58.66 (11)	H11A—C11—H11C	109.5
N1ⁱ—Li1—C9	142.5 (3)	H11B—C11—H11C	109.5
N1—Li1—C9	27.53 (11)	C14—C12—C15	108.5 (3)
N2—Li1—C9	58.66 (11)	C14—C12—C13	107.5 (3)
N2ⁱ—Li1—C9	128.53 (19)	C15—C12—C13	109.4 (3)
C9ⁱ—Li1—C9	169.3 (3)	C14—C12—Si1	111.8 (2)
N1ⁱ—Li1—C8	148.81 (15)	C15—C12—Si1	110.8 (3)
N1—Li1—C8	57.60 (12)	C13—C12—Si1	108.6 (3)
N2—Li1—C8	28.62 (10)	C12—C13—H13A	109.5
N2ⁱ—Li1—C8	121.7 (3)	C12—C13—H13B	109.5
C9ⁱ—Li1—C8	157.1 (2)	H13A—C13—H13B	109.5
C9—Li1—C8	30.47 (10)	C12—C13—H13C	109.5
N1ⁱ—Li1—C8ⁱ	57.60 (12)	H13A—C13—H13C	109.5
N1—Li1—C8ⁱ	148.81 (15)	H13B—C13—H13C	109.5
N2—Li1—C8ⁱ	121.7 (3)	C12—C14—H14A	109.5
N2ⁱ—Li1—C8ⁱ	28.62 (10)	C12—C14—H14B	109.5
C9ⁱ—Li1—C8ⁱ	30.47 (10)	H14A—C14—H14B	109.5
C9—Li1—C8ⁱ	157.1 (2)	C12—C14—H14C	109.5
C8—Li1—C8ⁱ	142.7 (3)	H14A—C14—H14C	109.5
N1ⁱ—Li1—Na1	120.0 (2)	H14B—C14—H14C	109.5
N1—Li1—Na1	120.0 (2)	C12—C15—H15A	109.5
N2—Li1—Na1	56.53 (18)	C12—C15—H15B	109.5
N2ⁱ—Li1—Na1	56.53 (18)	H15A—C15—H15B	109.5
C9ⁱ—Li1—Na1	95.34 (17)	C12—C15—H15C	109.5
C9—Li1—Na1	95.34 (17)	H15A—C15—H15C	109.5
C8—Li1—Na1	71.37 (16)	H15B—C15—H15C	109.5
C8ⁱ—Li1—Na1	71.37 (16)	N3—C16—H16A	109.5
C1—N1—C9	119.0 (4)	N3—C16—H16B	109.5
C1—N1—Li1	130.8 (3)	H16A—C16—H16B	109.5
C9—N1—Li1	108.9 (3)	N3—C16—H16C	109.5
C8—N2—Si1	124.2 (2)	H16A—C16—H16C	109.5
C8—N2—Li1	105.0 (2)	H16B—C16—H16C	109.5
Si1—N2—Li1	121.45 (14)	N3—C17—H17A	109.5
C8—N2—Na1	115.99 (18)	N3—C17—H17B	109.5
Si1—N2—Na1	102.07 (12)	H17A—C17—H17B	109.5
Li1—N2—Na1	79.64 (19)	N3—C17—H17C	109.5
C18—N3—C16	109.0 (6)	H17A—C17—H17C	109.5
C18—N3—C17	106.9 (5)	H17B—C17—H17C	109.5
C16—N3—C17	108.6 (5)	C18ⁱ—C18—N3	126.3 (3)
C18—N3—Na1	106.8 (3)	C18ⁱ—C18—H18A	105.8
C16—N3—Na1	106.6 (3)	N3—C18—H18A	105.8
C17—N3—Na1	118.6 (3)	C18ⁱ—C18—H18B	105.8
N1—C1—C2	123.3 (5)	N3—C18—H18B	105.8
N1—C1—H1A	118.4	H18A—C18—H18B	106.2
C2—C1—H1A	118.4

Symmetry code: (i) −x+2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[LiNa(C₁₅H₂₁N₂Si)₂(C₆H₁₆N₂)]
M_r	660.99
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	12.653 (2), 18.542 (3), 18.296 (3)
β (°)	108.794 (3)
V (Å³)	4063.6 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.962, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	11843, 4001, 2128
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.195, 0.97
No. of reflections	4001
No. of parameters	209
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.26

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by grants from the Natural Science Foundation of China (20702029) and the Natural Science Foundation of Shanxi Province (2008011024).

References

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