Di-μ-chlorido-bis­({2-[(triisopropyl­silyl)­amino­meth­yl]pyridine-κN}lithium(I))

Koch, C.; Görls, H.; Westerhausen, M.

doi:10.1107/S1600536807046442

Di-μ-chlorido-bis({2-[(triisopropylsilyl)aminomethyl]pyridine-κN}lithium(I))

The title compound, [Li₂Cl₂(C₁₅H₃₈N₂Si)₄], is a centrosymmetric dimer. Each Li atom is coordinated in a distorted tetrahedral manner by two pyridyl rings and two chloride anions. Only one of the two symmetry-independent NH groups is involved in hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046442/bt2518sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046442/bt2518Isup2.hkl Contains datablock I

CCDC reference: 667096

checkCIF report

Key indicators

Single-crystal X-ray study
T = 183 K
Mean (C-C) = 0.007 Å
R factor = 0.076
wR factor = 0.215
Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.87

Author Response: For high angles the scattering power of the crystal was very low. But the data parameter ratio looks very well.


Alert level B
REFLT03_ALERT_3_B  Reflection count < 90% complete (theta max?)
           From the CIF: _diffrn_reflns_theta_max           27.57
           From the CIF: _diffrn_reflns_theta_full          27.57
           From the CIF: _reflns_number_total               6997
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         8012
           Completeness (_total/calc)             87.33%

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.61 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C7B
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT420_ALERT_2_C D-H Without Acceptor       N2B    -   H1NB   ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         28

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In the past, metallated (2-pyridylmethyl)(trialkysilyl)amines were used for C–C coupling reactions in order to prepare tetradentate ligands. The zincation of (2-pyridylmethyl)(triisopropylsilyl)amine (A) gives dimeric methylzinc-(2-pyridylmethyl)(triisopropylsilyl)-amide. Further addition of dimethylzinc to a toluene solution to A at raised temperatures yields the C–C coupling product bis(methylzinc)[1,2-dipyridyl-1,2-bis(triisopropylsilylamido)ethane]. The synthesis of compound A is described but no structural data have been published (Westerhausen et al. 2002). An excess of LiCl led to the formation of single crystals of is[lithiumchloride-bis{(κN 2-pyridylmethyl)(triisopropylsilyl)amine}] ((A)₂LiCl]₂, 1) at ambient temperature. In 1, the (2-pyridylmethyl)(triisopropylsily)amines bond via the pyridyl-nitrogen atoms to the Li atoms forming a centosymmetric four-membered LiClLiⁱClⁱ ring [symmetry code:(i) 1 - x, 1 - y, 2 - z]. The amine reacts as a monodentate ligand. The lithium atoms in the central fragment Li₂Cl₂ have a transannular Li···Liⁱ distance of 292.5 (15) pm. The lithium atoms are distorted tetrahedral coordinated by two chloride atoms and two nitrogen atoms with LiCl bond lengths of 234.6 (7) pm and 235.5 (7) pm. These data are similar to those in [(THF)₂LiCl]₂ (Hahn & Rupprecht 1991, Hahn & Rupprecht 1991, Baker et al. 2005, Bickley et al. 2004, DeAngelis et al. 1992, Ho et al. 1993, Pratt et al. 2006, Solari et al. 1992, Tayebani et al. 1998). Due to this fact the bulkiness of the amines A is compareable of the THF molecules. The average Li···N distance of 210.0 pm in bis[lithiumchloride-bis{(κN2-pyridylmethyl) (di-tert-butylsilyl)amine}] (2, Westerhausen et al. 2004) is very similar to the values of 1 (209.8 (8) pm and 209.0 (8) pm) (Buttery et al. 2006; Chen et al. 2002; Engelhardt et al. 1988). In contrast to these LiCl adducts 1 and 2, dimeric LiI forms a 1/1 complex of bis[lithiumiodide-bis(2-pyridylmethyl)(tert-butyldimethylsilyl)amine] (Westerhausen et al. 2006). The lithiation of (2-pyridylmethyl)(tert-butyldimethylsilyl)amine in THF yields semi(tetrahydrofuran)lithium-(2-pyridylmethyl) (tert-butyldimethylsilyl)amide and the reaction with an other equivalent of methyllithium yields octameric dilithium (2-pyridylmethylido)(tert-butyldimethylsilyl)amide (Westerhausen et al. 2004). Reactions of halogenboranes with silylamines yield aminoboranes via elimination of chlorosilanes (Engelhardt et al., 1990).

Related literature top

For related literature, see: Baker et al. (2005); Bickley et al. (2004); Buttery et al. (2006); Chen et al. (2002); DeAngelis et al. (1992); Engelhardt et al. (1988, 1990); Hahn & Rupprecht (1991); Ho et al. (1993); Pratt et al. (2006); Solari et al. (1992); Tayebani et al. (1998); Westerhausen et al. (2002, 2004, 2006).

Experimental top

All manipulations were carried out in an atmosphere of argon using standard Schlenk techniques. THF and pentane were dried (Na/benzophenone) and distilled prior to use. 2-pyridylmethylamine and butyllithium were purchased form Aldrich. Tert-butyldimethylchlorosilane was purchased from Merck.¹H NMR and ¹³C NMR spectra were recorded at[D₆]benzene solution at ambient temperature on a Bruker AC 400 MHz s pectrometer and were referenced to deuterated benzene as an internal standard.

Bis[lithiumchloride-bis{(κN 2-pyridylmethyl)(triisopropylsilyl)amine}] was prepared according to a literature procedure (Westerhausen et al. 2002) and recrystallized from pentane. Reduction of the volume to 1/3 of the original volume, single crystals precipitated at ambient temperature within five days.

Physical data:

Mp: 52 °C (decomposition).

¹H NMR (400 MHz, Benzene [D6]) δ = 8.48 (d, ³J(H¹,H²) = 4.4, 1H, Pyr1); 7.61 (dt, ⁵J(H³,H¹) = 2.0, ³J(H³,H^2/4) = 7.4, 1H, Pyr3); 7.06 (d, ³J(H⁴,H³) = 7.6, 1H, Pyr4); 6.63 (t, ³J(H¹,H³) = 5.6, 1H, Pyr2); 4.15 (d, ³J(H⁶,NH) = 8.0, 2H, CH₂); 1.29 (s, br, 1H, NH); 1.07 (s, 21H, SiCH(CH₃)₂/ SiCH(CH₃)₂).

¹³C NMR (100 MHz, Benzene [D6]) δ = 163.25 (Pyr5); 149.28 (Pyr1); 135.80 (Pyr3); 121.29 (Pyr2); 120.68 (Pyr4); 48.62 (²J, CH2); 18.49 (CH₃); 13.91 (CH(CH₃)₂)

MS (EI, m/z [% '[%' %]]): 265 (M, 11), 264 (M⁺, 46), 263 (M⁺—H, 100), 223 (5), 222 (19), 221 (M⁺C₃H₇, 70), 220 (11), 219 (10), 136 (5), 135 (29), 134 (9), 87 (5), 73 (6), 59 (10).

IR (cm^-1): 3373, 3091, 3011, 2942, 2892, 2863, 2758, 2722, 1700, 1646, 1592, 1571, 1464, 1434, 1407, 1387, 1382, 1366, 1342, 1319, 1294, 1255, 1249, 1213, 1145, 1125, 1094, 1084, 1070, 1047, 1013, 994, 952, 918, 883, 841, 799, 752, 728, 680, 639, 602, 553, 502, 462, 402.

Structure description top

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1.n a i

The molecular structure of the title compound, showing 40% prabability displacement ellipsoides and the numbering scheme for the non-carbon atoms. H atoms have been omitted for clarity.

Di-µ-chlorido-bis({2-[(triisopropylsilyl)aminomethyl]pyridine-κN}lithium(I)) top

Crystal data top

[Li₂Cl₂(C₁₅H₃₈N₂Si)₄]	Z = 1
M_r = 1142.72	F(000) = 624
Triclinic, P1	D_x = 1.095 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6312 (19) Å	Cell parameters from 10497 reflections
b = 13.806 (3) Å	θ = 1.7–27.6°
c = 14.802 (3) Å	µ = 0.20 mm⁻¹
α = 113.036 (10)°	T = 183 K
β = 95.653 (17)°	Prism, colourless
γ = 102.388 (12)°	0.05 × 0.05 × 0.05 mm
V = 1732.2 (6) Å³

Data collection top

Nonius KappaCCD diffractometer	4247 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 27.6°, θ_min = 1.7°
φ and ω scans	h = −12→12
10497 measured reflections	k = −17→15
6997 independent reflections	l = −16→19

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.215	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0735P)² + 2.7204P] where P = (F_o² + 2F_c²)/3
6997 reflections	(Δ/σ)_max < 0.001
363 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Li₂Cl₂(C₁₅H₃₈N₂Si)₄]	γ = 102.388 (12)°
M_r = 1142.72	V = 1732.2 (6) Å³
Triclinic, P1	Z = 1
a = 9.6312 (19) Å	Mo Kα radiation
b = 13.806 (3) Å	µ = 0.20 mm⁻¹
c = 14.802 (3) Å	T = 183 K
α = 113.036 (10)°	0.05 × 0.05 × 0.05 mm
β = 95.653 (17)°

Data collection top

Nonius KappaCCD diffractometer	4247 reflections with I > 2σ(I)
10497 measured reflections	R_int = 0.039
6997 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.215	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.52 e Å⁻³
6997 reflections	Δρ_min = −0.36 e Å⁻³
363 parameters

Special details top

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

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

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

	x	y	z	U_iso*/U_eq
Li1	0.5468 (8)	0.4002 (6)	0.9583 (5)	0.0482 (17)
Cl1	0.47045 (13)	0.47397 (9)	1.11048 (8)	0.0521 (3)
Si1A	0.37243 (13)	0.16461 (10)	1.16902 (9)	0.0434 (3)
N1A	0.3840 (4)	0.2556 (3)	0.8693 (2)	0.0452 (8)
N2A	0.3501 (4)	0.2063 (3)	1.0739 (3)	0.0478 (9)
C1A	0.3073 (5)	0.2509 (4)	0.7861 (3)	0.0568 (12)
H1AA	0.3394	0.3083	0.7663	0.068*
C2A	0.1865 (5)	0.1689 (5)	0.7284 (4)	0.0651 (14)
H2AA	0.1373	0.1687	0.6694	0.078*
C3A	0.1368 (6)	0.0865 (4)	0.7568 (4)	0.0668 (14)
H3AA	0.0521	0.0285	0.7184	0.080*
C4A	0.2131 (5)	0.0899 (4)	0.8425 (4)	0.0591 (12)
H4AA	0.1808	0.0341	0.8641	0.071*
C5A	0.3355 (4)	0.1743 (3)	0.8965 (3)	0.0443 (10)
C6A	0.4233 (5)	0.1793 (4)	0.9897 (3)	0.0489 (10)
H6AA	0.4428	0.1075	0.9745	0.059*
H6AB	0.5179	0.2350	1.0087	0.059*
C7A	0.2504 (5)	0.2223 (4)	1.2538 (3)	0.0560 (12)
H7AA	0.2918	0.3036	1.2833	0.067*
C8A	0.2544 (7)	0.1923 (6)	1.3429 (4)	0.0862 (19)
H8AA	0.1994	0.2323	1.3894	0.129*
H8AB	0.3553	0.2119	1.3774	0.129*
H8AC	0.2111	0.1134	1.3189	0.129*
C9A	0.0954 (5)	0.2001 (5)	1.2028 (4)	0.0686 (14)
H9AA	0.0476	0.2483	1.2490	0.103*
H9AB	0.0430	0.1236	1.1835	0.103*
H9AC	0.0954	0.2142	1.1428	0.103*
C10A	0.3299 (5)	0.0107 (3)	1.1087 (3)	0.0457 (10)
H10A	0.3907	−0.0074	1.0566	0.055*
C11A	0.1722 (5)	−0.0475 (4)	1.0525 (4)	0.0671 (13)
H11A	0.1629	−0.1248	1.0110	0.101*
H11B	0.1442	−0.0130	1.0097	0.101*
H11C	0.1085	−0.0419	1.1010	0.101*
C12A	0.3745 (6)	−0.0382 (4)	1.1805 (4)	0.0612 (13)
H12A	0.3572	−0.1175	1.1430	0.092*
H12B	0.3169	−0.0239	1.2329	0.092*
H12C	0.4778	−0.0045	1.2113	0.092*
C13A	0.5639 (5)	0.2228 (4)	1.2452 (3)	0.0482 (10)
H13A	0.5671	0.1962	1.2990	0.058*
C14A	0.6065 (5)	0.3484 (4)	1.2971 (4)	0.0622 (13)
H14A	0.7085	0.3760	1.3317	0.093*
H14B	0.5452	0.3723	1.3459	0.093*
H14C	0.5930	0.3771	1.2469	0.093*
C15A	0.6740 (5)	0.1829 (4)	1.1828 (4)	0.0611 (13)
H15A	0.7703	0.2100	1.2264	0.092*
H15B	0.6769	0.2105	1.1311	0.092*
H15C	0.6456	0.1027	1.1510	0.092*
Si1B	0.79713 (13)	0.28106 (10)	0.60696 (8)	0.0474 (3)
N1B	0.7537 (4)	0.3767 (3)	0.9785 (2)	0.0433 (8)
N2B	0.8546 (5)	0.3306 (4)	0.7349 (3)	0.0536 (10)
C1B	0.8156 (5)	0.3954 (3)	1.0715 (3)	0.0479 (10)
H1BA	0.7613	0.4149	1.1229	0.057*
C2B	0.9527 (5)	0.3878 (4)	1.0962 (3)	0.0530 (11)
H2BA	0.9916	0.4010	1.1628	0.064*
C3B	1.0328 (5)	0.3606 (4)	1.0225 (4)	0.0564 (12)
H3BA	1.1284	0.3554	1.0373	0.068*
C4B	0.9709 (5)	0.3411 (4)	0.9262 (3)	0.0508 (11)
H4BA	1.0241	0.3220	0.8742	0.061*
C5B	0.8324 (4)	0.3493 (3)	0.9062 (3)	0.0434 (9)
C6B	0.7567 (5)	0.3295 (4)	0.8040 (3)	0.0519 (11)
H6BA	0.6824	0.2577	0.7746	0.062*
H6BB	0.7058	0.3866	0.8115	0.062*
C7B	0.6639 (5)	0.3478 (4)	0.5710 (3)	0.0573 (12)
H7BA	0.6485	0.3220	0.4966	0.069*
C8B	0.7227 (8)	0.4725 (5)	0.6175 (5)	0.0914 (19)
H8BA	0.6538	0.5035	0.5924	0.137*
H8BB	0.8162	0.4927	0.5994	0.137*
H8BC	0.7357	0.5012	0.6906	0.137*
C9B	0.5148 (6)	0.3168 (6)	0.5962 (4)	0.0822 (18)
H9BA	0.4484	0.3487	0.5701	0.123*
H9BB	0.5248	0.3448	0.6691	0.123*
H9BC	0.4761	0.2368	0.5656	0.123*
C10B	0.9672 (5)	0.3055 (4)	0.5550 (3)	0.0609 (13)
H10B	0.9979	0.2366	0.5362	0.073*
C11B	1.0943 (6)	0.3945 (5)	0.6265 (4)	0.0847 (18)
H11D	1.1781	0.3963	0.5941	0.127*
H11E	1.1171	0.3810	0.6857	0.127*
H11F	1.0714	0.4650	0.6468	0.127*
C12B	0.9371 (6)	0.3185 (5)	0.4578 (4)	0.0725 (15)
H12D	1.0268	0.3275	0.4322	0.109*
H12E	0.9015	0.3831	0.4707	0.109*
H12F	0.8635	0.2532	0.4080	0.109*
C13B	0.7081 (5)	0.1308 (4)	0.5560 (3)	0.0580 (12)
H13B	0.6231	0.1229	0.5888	0.070*
C14B	0.8030 (7)	0.0662 (5)	0.5822 (5)	0.0814 (17)
H14D	0.7452	−0.0095	0.5610	0.122*
H14E	0.8401	0.1000	0.6547	0.122*
H14F	0.8846	0.0667	0.5475	0.122*
C15B	0.6462 (7)	0.0775 (4)	0.4429 (4)	0.0735 (15)
H15D	0.5995	−0.0006	0.4211	0.110*
H15E	0.7250	0.0862	0.4071	0.110*
H15F	0.5745	0.1129	0.4282	0.110*
H1NB	0.925 (6)	0.391 (4)	0.764 (4)	0.067 (16)*
H1NA	0.347 (4)	0.269 (4)	1.095 (3)	0.038 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Li1	0.048 (4)	0.057 (5)	0.046 (4)	0.013 (3)	0.010 (3)	0.028 (4)
Cl1	0.0677 (7)	0.0551 (7)	0.0490 (6)	0.0241 (5)	0.0230 (5)	0.0317 (5)
Si1A	0.0457 (6)	0.0484 (7)	0.0429 (6)	0.0169 (5)	0.0108 (5)	0.0240 (5)
N1A	0.0460 (19)	0.053 (2)	0.0428 (19)	0.0142 (16)	0.0096 (16)	0.0265 (17)
N2A	0.057 (2)	0.050 (2)	0.048 (2)	0.0246 (19)	0.0137 (18)	0.0262 (19)
C1A	0.059 (3)	0.070 (3)	0.049 (3)	0.010 (2)	0.006 (2)	0.038 (2)
C2A	0.059 (3)	0.088 (4)	0.051 (3)	0.011 (3)	0.004 (2)	0.039 (3)
C3A	0.058 (3)	0.064 (3)	0.066 (3)	−0.001 (2)	−0.001 (3)	0.026 (3)
C4A	0.055 (3)	0.061 (3)	0.066 (3)	0.009 (2)	0.006 (2)	0.037 (3)
C5A	0.043 (2)	0.051 (3)	0.049 (2)	0.019 (2)	0.014 (2)	0.026 (2)
C6A	0.048 (2)	0.061 (3)	0.050 (2)	0.017 (2)	0.013 (2)	0.035 (2)
C7A	0.058 (3)	0.065 (3)	0.051 (3)	0.027 (2)	0.013 (2)	0.025 (2)
C8A	0.084 (4)	0.155 (6)	0.055 (3)	0.069 (4)	0.036 (3)	0.058 (4)
C9A	0.058 (3)	0.102 (4)	0.060 (3)	0.038 (3)	0.019 (3)	0.038 (3)
C10A	0.050 (2)	0.051 (3)	0.043 (2)	0.016 (2)	0.015 (2)	0.025 (2)
C11A	0.061 (3)	0.059 (3)	0.070 (3)	0.008 (2)	0.009 (3)	0.022 (3)
C12A	0.083 (3)	0.058 (3)	0.059 (3)	0.024 (3)	0.023 (3)	0.038 (2)
C13A	0.050 (2)	0.056 (3)	0.046 (2)	0.015 (2)	0.007 (2)	0.030 (2)
C14A	0.062 (3)	0.059 (3)	0.064 (3)	0.010 (2)	−0.001 (2)	0.031 (3)
C15A	0.046 (3)	0.080 (4)	0.064 (3)	0.017 (2)	0.005 (2)	0.038 (3)
Si1B	0.0501 (7)	0.0587 (8)	0.0385 (6)	0.0154 (6)	0.0138 (5)	0.0246 (6)
N1B	0.0459 (19)	0.049 (2)	0.0409 (18)	0.0117 (16)	0.0099 (16)	0.0253 (16)
N2B	0.057 (2)	0.065 (3)	0.040 (2)	0.010 (2)	0.0155 (19)	0.025 (2)
C1B	0.054 (3)	0.052 (3)	0.040 (2)	0.010 (2)	0.010 (2)	0.023 (2)
C2B	0.054 (3)	0.061 (3)	0.047 (2)	0.014 (2)	0.003 (2)	0.028 (2)
C3B	0.049 (3)	0.063 (3)	0.062 (3)	0.018 (2)	0.004 (2)	0.033 (3)
C4B	0.051 (3)	0.061 (3)	0.048 (2)	0.019 (2)	0.018 (2)	0.027 (2)
C5B	0.046 (2)	0.046 (2)	0.045 (2)	0.0135 (19)	0.013 (2)	0.024 (2)
C6B	0.055 (3)	0.067 (3)	0.041 (2)	0.021 (2)	0.013 (2)	0.028 (2)
C7B	0.065 (3)	0.069 (3)	0.047 (2)	0.029 (3)	0.018 (2)	0.027 (2)
C8B	0.127 (5)	0.075 (4)	0.087 (4)	0.053 (4)	0.029 (4)	0.035 (3)
C9B	0.066 (3)	0.136 (6)	0.056 (3)	0.046 (4)	0.015 (3)	0.043 (3)
C10B	0.058 (3)	0.080 (4)	0.050 (3)	0.017 (3)	0.017 (2)	0.033 (3)
C11B	0.070 (4)	0.102 (5)	0.078 (4)	0.001 (3)	0.030 (3)	0.041 (4)
C12B	0.078 (4)	0.103 (4)	0.060 (3)	0.031 (3)	0.031 (3)	0.050 (3)
C13B	0.062 (3)	0.063 (3)	0.049 (3)	0.011 (2)	0.005 (2)	0.028 (2)
C14B	0.091 (4)	0.068 (4)	0.088 (4)	0.020 (3)	−0.002 (3)	0.041 (3)
C15B	0.092 (4)	0.061 (3)	0.054 (3)	0.007 (3)	−0.001 (3)	0.021 (3)

Geometric parameters (Å, º) top

Li1—N1A	2.090 (8)	C15A—H15A	0.9800
Li1—N1B	2.098 (8)	C15A—H15B	0.9800
Li1—Cl1	2.346 (7)	C15A—H15C	0.9800
Li1—Cl1ⁱ	2.357 (7)	Si1B—N2B	1.726 (4)
Li1—Li1ⁱ	2.925 (15)	Si1B—C13B	1.869 (5)
Cl1—Li1ⁱ	2.357 (7)	Si1B—C7B	1.881 (5)
Si1A—N2A	1.728 (4)	Si1B—C10B	1.898 (5)
Si1A—C7A	1.871 (5)	N1B—C1B	1.346 (5)
Si1A—C10A	1.885 (4)	N1B—C5B	1.353 (5)
Si1A—C13A	1.888 (4)	N2B—C6B	1.460 (5)
N1A—C1A	1.343 (5)	N2B—H1NB	0.87 (5)
N1A—C5A	1.345 (5)	C1B—C2B	1.372 (6)
N2A—C6A	1.454 (5)	C1B—H1BA	0.9500
N2A—H1NA	0.81 (4)	C2B—C3B	1.376 (6)
C1A—C2A	1.359 (7)	C2B—H2BA	0.9500
C1A—H1AA	0.9500	C3B—C4B	1.386 (6)
C2A—C3A	1.371 (7)	C3B—H3BA	0.9500
C2A—H2AA	0.9500	C4B—C5B	1.376 (6)
C3A—C4A	1.381 (7)	C4B—H4BA	0.9500
C3A—H3AA	0.9500	C5B—C6B	1.506 (6)
C4A—C5A	1.372 (6)	C6B—H6BA	0.9900
C4A—H4AA	0.9500	C6B—H6BB	0.9900
C5A—C6A	1.514 (6)	C7B—C8B	1.528 (8)
C6A—H6AA	0.9900	C7B—C9B	1.533 (7)
C6A—H6AB	0.9900	C7B—H7BA	1.0000
C7A—C9A	1.514 (6)	C8B—H8BA	0.9800
C7A—C8A	1.529 (6)	C8B—H8BB	0.9800
C7A—H7AA	1.0000	C8B—H8BC	0.9800
C8A—H8AA	0.9800	C9B—H9BA	0.9800
C8A—H8AB	0.9800	C9B—H9BB	0.9800
C8A—H8AC	0.9800	C9B—H9BC	0.9800
C9A—H9AA	0.9800	C10B—C11B	1.487 (7)
C9A—H9AB	0.9800	C10B—C12B	1.526 (6)
C9A—H9AC	0.9800	C10B—H10B	1.0000
C10A—C11A	1.533 (6)	C11B—H11D	0.9800
C10A—C12A	1.538 (6)	C11B—H11E	0.9800
C10A—H10A	1.0000	C11B—H11F	0.9800
C11A—H11A	0.9800	C12B—H12D	0.9800
C11A—H11B	0.9800	C12B—H12E	0.9800
C11A—H11C	0.9800	C12B—H12F	0.9800
C12A—H12A	0.9800	C13B—C14B	1.526 (7)
C12A—H12B	0.9800	C13B—C15B	1.533 (6)
C12A—H12C	0.9800	C13B—H13B	1.0000
C13A—C15A	1.525 (6)	C14B—H14D	0.9800
C13A—C14A	1.534 (6)	C14B—H14E	0.9800
C13A—H13A	1.0000	C14B—H14F	0.9800
C14A—H14A	0.9800	C15B—H15D	0.9800
C14A—H14B	0.9800	C15B—H15E	0.9800
C14A—H14C	0.9800	C15B—H15F	0.9800

N1A—Li1—N1B	113.6 (4)	C13A—C15A—H15B	109.5
N1A—Li1—Cl1	105.2 (3)	H15A—C15A—H15B	109.5
N1B—Li1—Cl1	112.2 (3)	C13A—C15A—H15C	109.5
N1A—Li1—Cl1ⁱ	106.9 (3)	H15A—C15A—H15C	109.5
N1B—Li1—Cl1ⁱ	114.9 (3)	H15B—C15A—H15C	109.5
Cl1—Li1—Cl1ⁱ	103.1 (3)	N2B—Si1B—C13B	108.2 (2)
N1A—Li1—Li1ⁱ	116.4 (4)	N2B—Si1B—C7B	113.3 (2)
N1B—Li1—Li1ⁱ	130.0 (5)	C13B—Si1B—C7B	108.4 (2)
Cl1—Li1—Li1ⁱ	51.7 (2)	N2B—Si1B—C10B	106.1 (2)
Cl1ⁱ—Li1—Li1ⁱ	51.4 (2)	C13B—Si1B—C10B	109.8 (2)
Li1—Cl1—Li1ⁱ	76.9 (3)	C7B—Si1B—C10B	110.9 (2)
N2A—Si1A—C7A	105.29 (19)	C1B—N1B—C5B	117.5 (4)
N2A—Si1A—C10A	107.33 (19)	C1B—N1B—Li1	117.5 (3)
C7A—Si1A—C10A	115.7 (2)	C5B—N1B—Li1	124.9 (3)
N2A—Si1A—C13A	112.41 (19)	C6B—N2B—Si1B	123.8 (3)
C7A—Si1A—C13A	107.6 (2)	C6B—N2B—H1NB	108 (3)
C10A—Si1A—C13A	108.56 (19)	Si1B—N2B—H1NB	117 (3)
C1A—N1A—C5A	117.0 (4)	N1B—C1B—C2B	123.6 (4)
C1A—N1A—Li1	117.4 (3)	N1B—C1B—H1BA	118.2
C5A—N1A—Li1	124.8 (3)	C2B—C1B—H1BA	118.2
C6A—N2A—Si1A	124.7 (3)	C1B—C2B—C3B	118.7 (4)
C6A—N2A—H1NA	111 (3)	C1B—C2B—H2BA	120.7
Si1A—N2A—H1NA	112 (3)	C3B—C2B—H2BA	120.7
N1A—C1A—C2A	124.0 (4)	C2B—C3B—C4B	118.6 (4)
N1A—C1A—H1AA	118.0	C2B—C3B—H3BA	120.7
C2A—C1A—H1AA	118.0	C4B—C3B—H3BA	120.7
C1A—C2A—C3A	118.8 (4)	C5B—C4B—C3B	119.9 (4)
C1A—C2A—H2AA	120.6	C5B—C4B—H4BA	120.0
C3A—C2A—H2AA	120.6	C3B—C4B—H4BA	120.0
C2A—C3A—C4A	118.3 (5)	N1B—C5B—C4B	121.7 (4)
C2A—C3A—H3AA	120.8	N1B—C5B—C6B	114.7 (4)
C4A—C3A—H3AA	120.8	C4B—C5B—C6B	123.6 (4)
C5A—C4A—C3A	119.8 (4)	N2B—C6B—C5B	113.5 (4)
C5A—C4A—H4AA	120.1	N2B—C6B—H6BA	108.9
C3A—C4A—H4AA	120.1	C5B—C6B—H6BA	108.9
N1A—C5A—C4A	122.0 (4)	N2B—C6B—H6BB	108.9
N1A—C5A—C6A	116.8 (4)	C5B—C6B—H6BB	108.9
C4A—C5A—C6A	121.2 (4)	H6BA—C6B—H6BB	107.7
N2A—C6A—C5A	112.7 (3)	C8B—C7B—C9B	109.2 (5)
N2A—C6A—H6AA	109.1	C8B—C7B—Si1B	112.1 (4)
C5A—C6A—H6AA	109.1	C9B—C7B—Si1B	113.8 (4)
N2A—C6A—H6AB	109.1	C8B—C7B—H7BA	107.1
C5A—C6A—H6AB	109.1	C9B—C7B—H7BA	107.1
H6AA—C6A—H6AB	107.8	Si1B—C7B—H7BA	107.1
C9A—C7A—C8A	110.9 (4)	C7B—C8B—H8BA	109.5
C9A—C7A—Si1A	115.6 (3)	C7B—C8B—H8BB	109.5
C8A—C7A—Si1A	112.8 (3)	H8BA—C8B—H8BB	109.5
C9A—C7A—H7AA	105.5	C7B—C8B—H8BC	109.5
C8A—C7A—H7AA	105.5	H8BA—C8B—H8BC	109.5
Si1A—C7A—H7AA	105.5	H8BB—C8B—H8BC	109.5
C7A—C8A—H8AA	109.5	C7B—C9B—H9BA	109.5
C7A—C8A—H8AB	109.5	C7B—C9B—H9BB	109.5
H8AA—C8A—H8AB	109.5	H9BA—C9B—H9BB	109.5
C7A—C8A—H8AC	109.5	C7B—C9B—H9BC	109.5
H8AA—C8A—H8AC	109.5	H9BA—C9B—H9BC	109.5
H8AB—C8A—H8AC	109.5	H9BB—C9B—H9BC	109.5
C7A—C9A—H9AA	109.5	C11B—C10B—C12B	110.8 (4)
C7A—C9A—H9AB	109.5	C11B—C10B—Si1B	116.0 (3)
H9AA—C9A—H9AB	109.5	C12B—C10B—Si1B	112.4 (3)
C7A—C9A—H9AC	109.5	C11B—C10B—H10B	105.5
H9AA—C9A—H9AC	109.5	C12B—C10B—H10B	105.5
H9AB—C9A—H9AC	109.5	Si1B—C10B—H10B	105.5
C11A—C10A—C12A	110.6 (4)	C10B—C11B—H11D	109.5
C11A—C10A—Si1A	113.9 (3)	C10B—C11B—H11E	109.5
C12A—C10A—Si1A	113.9 (3)	H11D—C11B—H11E	109.5
C11A—C10A—H10A	105.9	C10B—C11B—H11F	109.5
C12A—C10A—H10A	105.9	H11D—C11B—H11F	109.5
Si1A—C10A—H10A	105.9	H11E—C11B—H11F	109.5
C10A—C11A—H11A	109.5	C10B—C12B—H12D	109.5
C10A—C11A—H11B	109.5	C10B—C12B—H12E	109.5
H11A—C11A—H11B	109.5	H12D—C12B—H12E	109.5
C10A—C11A—H11C	109.5	C10B—C12B—H12F	109.5
H11A—C11A—H11C	109.5	H12D—C12B—H12F	109.5
H11B—C11A—H11C	109.5	H12E—C12B—H12F	109.5
C10A—C12A—H12A	109.5	C14B—C13B—C15B	110.2 (4)
C10A—C12A—H12B	109.5	C14B—C13B—Si1B	114.1 (4)
H12A—C12A—H12B	109.5	C15B—C13B—Si1B	113.4 (3)
C10A—C12A—H12C	109.5	C14B—C13B—H13B	106.1
H12A—C12A—H12C	109.5	C15B—C13B—H13B	106.1
H12B—C12A—H12C	109.5	Si1B—C13B—H13B	106.1
C15A—C13A—C14A	110.7 (4)	C13B—C14B—H14D	109.5
C15A—C13A—Si1A	112.3 (3)	C13B—C14B—H14E	109.5
C14A—C13A—Si1A	111.6 (3)	H14D—C14B—H14E	109.5
C15A—C13A—H13A	107.3	C13B—C14B—H14F	109.5
C14A—C13A—H13A	107.3	H14D—C14B—H14F	109.5
Si1A—C13A—H13A	107.3	H14E—C14B—H14F	109.5
C13A—C14A—H14A	109.5	C13B—C15B—H15D	109.5
C13A—C14A—H14B	109.5	C13B—C15B—H15E	109.5
H14A—C14A—H14B	109.5	H15D—C15B—H15E	109.5
C13A—C14A—H14C	109.5	C13B—C15B—H15F	109.5
H14A—C14A—H14C	109.5	H15D—C15B—H15F	109.5
H14B—C14A—H14C	109.5	H15E—C15B—H15F	109.5
C13A—C15A—H15A	109.5

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1NA···Cl1	0.81 (5)	2.73 (6)	3.430 (5)	146 (4)

Experimental details

Crystal data
Chemical formula	[Li₂Cl₂(C₁₅H₃₈N₂Si)₄]
M_r	1142.72
Crystal system, space group	Triclinic, P1
Temperature (K)	183
a, b, c (Å)	9.6312 (19), 13.806 (3), 14.802 (3)
α, β, γ (°)	113.036 (10), 95.653 (17), 102.388 (12)
V (Å³)	1732.2 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.05 × 0.05 × 0.05

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10497, 6997, 4247
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.215, 1.05
No. of reflections	6997
No. of parameters	363
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.36

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Siemens, 1990).