Bis[μ2-1,1-(butane-1,4-di­yl)-2,3-dicyclo­hexyl­guanidinato]bis­[(tetra­hydro­furan)­lithium](Li—Li)

Han, H.; Li, W.; Li, H.

doi:10.1107/S1600536810046477

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1579

https://doi.org/10.1107/S1600536810046477

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Bis[μ₂-1,1-(butane-1,4-diyl)-2,3-dicyclohexylguanidinato]bis[(tetrahydrofuran)lithium](Li—Li)

Hongfei Han,^a Wenjuan Li ^a and Haoyang Li ^a ^*

^aDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China
^*Correspondence e-mail: hhf_2222@yahoo.com.cn

(Received 17 September 2010; accepted 10 November 2010; online 17 November 2010)

In the dinuclear centrosymmetric title complex, [Li₂(C₁₇H₃₀N₃)₂(C₄H₈O)₂], the Li⁺ cation is coordinated by three N atoms from two guanidinate ligands and an O atom from tetrahydrofuran (THF) in a strongly distorted tetrahedral environment. In the guanidinate-bridged THF-stabilized dimer the Li⋯Li separation is short at 2.479 (8) Å.

Related literature

For related guanidinato compounds, see: Chandra et al. (1970 ); Barker & Kilner (1994 ); Bailey & Pace (2001 ); Coles & Hitchcock (2004 ); Corey et al. (2006 ); Zhou et al. (2007 ).

Experimental

Crystal data

[Li₂(C₁₇H₃₀N₃)₂(C₄H₈O)₂]
M_r = 710.97
Monoclinic, P 2₁ /c
a = 10.446 (6) Å
b = 21.454 (15) Å
c = 10.491 (6) Å
β = 114.13 (4)°
V = 2146 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 223 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.980, T_max = 0.987
8457 measured reflections
3688 independent reflections
2749 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.237
S = 1.05
3688 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Selected bond lengths (Å)

Li—O	1.973 (5)
Li—N2ⁱ	1.997 (5)
Li—N1	2.057 (5)
Li—N1ⁱ	2.204 (5)
Symmetry code: (i) -x+2, -y, -z+1.

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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810046477/jj2061sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046477/jj2061Isup2.hkl

checkCIF report

Comment top

As a result of the donor ability of the nitrogen centers and the potential to exploit both the steric and electronic effects induced by the programmed variation of organic substituents,the guanidinate anion has generated significant interest as a ligand (Bailey & Pace, 2001; Barker & Kilner, 1994). Since the first guanidinato complexes have been reported (Chandra et al., 1970), guanidinato ligands have been used extensively in the coordination chemistry of transition, f-block, and main-group metals (Corey et al., 2006). Moreover many guanidinato complexes were reported showing good performance in ethylene polymerization (Zhou et al., 2007) and in ring-opening polymerisation reactions (Coles & Hitchcock, 2004) in catalysis applications.

In the title complex,[(THF)LiN(C₆H₁₁)C(NC₄H₈)N(C₆H₁₁)]₂ , the Li cation is coordinated by three N atoms from two guanidinato ligands and an O atom from tetrahydrofuran as a dimer around a planar Li/N1/LiA/N1A ring (Fig. 1). The core of the centrosymmetric molecule has a fused tricyclic ladder motif comprising a central planar Li/N1/LiA/N1A ring flanked by planar N2/C1/N1/LiA and N2A/C1A/N1A/Li rings. The dihedral angle between the latter two rings is 46.4 (9)°. Inside the guanidinato-bridged THF-stabilized dimer the Li···Li separation is short at 2.479 (8) Å. Electronic delocalization throughout the guanidinate moiety is observed as evidenced by the C-N distances [N1—C1: 1.355 (3) Å, N2—C1: 1.314 (3) Å].

Related literature top

For related guanidinato compounds, see: Chandra et al. (1970); Barker et al. (1994); Bailey et al. (2001); Coles et al. (2004); Corey et al. (2006); Zhou et al. (2007).

Experimental top

A solution of N-tetrahydropyrrolyl lithium in diethylether (0.232g, 3mmol) was added dropwise with stirring at 0 C to a solution of N,N'-dicyclohexyl carbodiimide (0.619g, 3mmol) in ether. The mixture was warmed to room temperature and stirred for 2h. The solvent was removed under reduced pressure. The resulting white precipitate was washed with hexane and dried in vacuo. The residue was dissolved in a mixed solvent of THF and hexane, and then filtered. The concentration of the filtrate under reduced pressure gave the colorless crystals suitable for X-ray analysis over several days (yield 0.534g, 50%).

Structure description top

For related guanidinato compounds, see: Chandra et al. (1970); Barker et al. (1994); Bailey et al. (2001); Coles et al. (2004); Corey et al. (2006); Zhou et al. (2007).

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: SHELXTL (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 have been omitted for clarity.

Bis[µ₂-1,1-(butane-1,4-diyl)-2,3- dicyclohexylguanidinato]bis[(tetrahydrofuran)lithium](Li—Li) top

Crystal data top

[Li₂(C₁₇H₃₀N₃)₂(C₄H₈O)₂]	F(000) = 784
M_r = 710.97	D_x = 1.100 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1854 reflections
a = 10.446 (6) Å	θ = 1.9–25.0°
b = 21.454 (15) Å	µ = 0.07 mm⁻¹
c = 10.491 (6) Å	T = 223 K
β = 114.13 (4)°	Block, colorless
V = 2146 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3688 independent reflections
Radiation source: fine-focus sealed tube	2749 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.980, T_max = 0.987	k = −25→25
8457 measured reflections	l = −12→10

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.237	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1491P)² + 0.6111P] where P = (F_o² + 2F_c²)/3
3688 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Li₂(C₁₇H₃₀N₃)₂(C₄H₈O)₂]	V = 2146 (2) Å³
M_r = 710.97	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.446 (6) Å	µ = 0.07 mm⁻¹
b = 21.454 (15) Å	T = 223 K
c = 10.491 (6) Å	0.30 × 0.20 × 0.20 mm
β = 114.13 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3688 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2749 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.987	R_int = 0.042
8457 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.237	H-atom parameters constrained
S = 1.05	Δρ_max = 0.68 e Å⁻³
3688 reflections	Δρ_min = −0.61 e Å⁻³
235 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
Li	1.0428 (4)	0.04287 (19)	0.4484 (4)	0.0287 (9)
N1	0.8388 (2)	0.03737 (9)	0.4284 (2)	0.0258 (5)
N2	0.7869 (2)	−0.06576 (9)	0.3820 (2)	0.0282 (5)
N3	0.6042 (2)	0.00733 (10)	0.2715 (2)	0.0311 (6)
O	1.0417 (2)	0.06534 (9)	0.26561 (19)	0.0396 (5)
C1	0.7440 (2)	−0.00756 (11)	0.3611 (2)	0.0245 (6)
C2	0.7853 (2)	0.09453 (10)	0.4653 (3)	0.0254 (6)
H2	0.6822	0.0952	0.4121	0.030*
C3	0.8457 (3)	0.15283 (11)	0.4260 (3)	0.0316 (6)
H3A	0.9480	0.1527	0.4764	0.038*
H3B	0.8232	0.1521	0.3257	0.038*
C4	0.7868 (3)	0.21241 (13)	0.4613 (3)	0.0442 (8)
H4A	0.8314	0.2486	0.4396	0.053*
H4B	0.6858	0.2148	0.4032	0.053*
C5	0.8114 (3)	0.21468 (13)	0.6146 (3)	0.0465 (8)
H5A	0.9120	0.2188	0.6725	0.056*
H5B	0.7639	0.2512	0.6311	0.056*
C6	0.7565 (4)	0.15618 (14)	0.6565 (3)	0.0476 (8)
H6A	0.6539	0.1553	0.6083	0.057*
H6B	0.7811	0.1573	0.7572	0.057*
C7	0.8164 (3)	0.09684 (12)	0.6211 (3)	0.0359 (7)
H7A	0.7751	0.0603	0.6459	0.043*
H7B	0.9180	0.0955	0.6761	0.043*
C8	0.7020 (2)	−0.11505 (11)	0.2911 (3)	0.0284 (6)
H8	0.6187	−0.0960	0.2164	0.034*
C9	0.6532 (3)	−0.16101 (12)	0.3720 (3)	0.0369 (7)
H9A	0.5972	−0.1388	0.4131	0.044*
H9B	0.7352	−0.1787	0.4485	0.044*
C10	0.5658 (3)	−0.21360 (14)	0.2799 (3)	0.0456 (8)
H10A	0.5389	−0.2428	0.3366	0.055*
H10B	0.4799	−0.1964	0.2077	0.055*
C11	0.6480 (4)	−0.24799 (14)	0.2117 (4)	0.0545 (9)
H11A	0.7279	−0.2693	0.2837	0.065*
H11B	0.5879	−0.2797	0.1479	0.065*
C12	0.7002 (4)	−0.20397 (15)	0.1320 (4)	0.0542 (9)
H12A	0.6200	−0.1869	0.0525	0.065*
H12B	0.7588	−0.2270	0.0952	0.065*
C13	0.7857 (3)	−0.15020 (13)	0.2236 (3)	0.0415 (7)
H13A	0.8125	−0.1213	0.1665	0.050*
H13B	0.8718	−0.1668	0.2968	0.050*
C14	0.5631 (3)	0.05740 (13)	0.1696 (3)	0.0355 (7)
H14A	0.5720	0.0446	0.0839	0.043*
H14B	0.6209	0.0945	0.2072	0.043*
C15	0.4109 (4)	0.0700 (2)	0.1417 (5)	0.0731 (12)
H15A	0.3945	0.1149	0.1436	0.088*
H15B	0.3486	0.0536	0.0499	0.088*
C16	0.3846 (4)	0.0377 (2)	0.2543 (5)	0.0751 (13)
H16A	0.4007	0.0661	0.3326	0.090*
H16B	0.2879	0.0224	0.2191	0.090*
C17	0.4850 (3)	−0.01453 (14)	0.2982 (3)	0.0431 (7)
H17A	0.4439	−0.0521	0.2436	0.052*
H17B	0.5136	−0.0238	0.3976	0.052*
C18	1.0836 (3)	0.12480 (14)	0.2329 (3)	0.0439 (8)
H18A	1.1860	0.1283	0.2730	0.053*
H18B	1.0456	0.1586	0.2699	0.053*
C19	1.0247 (4)	0.12776 (17)	0.0757 (4)	0.0571 (9)
H19A	1.0054	0.1708	0.0421	0.069*
H19B	1.0884	0.1085	0.0398	0.069*
C20	0.8910 (4)	0.09066 (19)	0.0352 (4)	0.0636 (10)
H20A	0.8603	0.0738	−0.0595	0.076*
H20B	0.8156	0.1162	0.0406	0.076*
C21	0.9332 (3)	0.03918 (16)	0.1427 (3)	0.0501 (8)
H21A	0.8531	0.0260	0.1621	0.060*
H21B	0.9685	0.0030	0.1097	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Li	0.023 (2)	0.028 (2)	0.032 (2)	−0.0009 (17)	0.0092 (18)	0.0017 (17)
N1	0.0210 (11)	0.0210 (10)	0.0326 (12)	−0.0009 (8)	0.0081 (9)	−0.0012 (8)
N2	0.0259 (11)	0.0206 (11)	0.0306 (12)	0.0000 (8)	0.0039 (9)	−0.0021 (8)
N3	0.0183 (11)	0.0282 (11)	0.0417 (13)	−0.0008 (8)	0.0070 (9)	0.0063 (9)
O	0.0414 (12)	0.0434 (12)	0.0326 (11)	−0.0087 (9)	0.0137 (9)	0.0035 (8)
C1	0.0214 (13)	0.0262 (13)	0.0261 (13)	−0.0007 (10)	0.0099 (10)	0.0014 (10)
C2	0.0208 (12)	0.0216 (12)	0.0316 (14)	0.0022 (9)	0.0085 (10)	0.0003 (10)
C3	0.0350 (15)	0.0244 (13)	0.0347 (15)	−0.0012 (11)	0.0134 (12)	0.0015 (10)
C4	0.0527 (19)	0.0236 (14)	0.0531 (19)	0.0045 (12)	0.0185 (15)	0.0043 (13)
C5	0.0525 (19)	0.0311 (15)	0.0538 (19)	0.0050 (13)	0.0197 (15)	−0.0099 (13)
C6	0.062 (2)	0.0454 (18)	0.0457 (18)	0.0076 (15)	0.0319 (16)	−0.0051 (14)
C7	0.0409 (16)	0.0305 (14)	0.0397 (16)	0.0016 (12)	0.0201 (13)	0.0028 (12)
C8	0.0235 (13)	0.0246 (13)	0.0307 (14)	−0.0004 (10)	0.0044 (11)	−0.0011 (10)
C9	0.0390 (16)	0.0295 (14)	0.0390 (16)	−0.0051 (12)	0.0128 (13)	−0.0024 (12)
C10	0.0472 (18)	0.0338 (16)	0.0488 (18)	−0.0121 (13)	0.0124 (14)	−0.0023 (13)
C11	0.054 (2)	0.0286 (16)	0.065 (2)	−0.0043 (14)	0.0080 (17)	−0.0133 (15)
C12	0.056 (2)	0.0511 (19)	0.057 (2)	−0.0076 (16)	0.0242 (17)	−0.0267 (16)
C13	0.0385 (16)	0.0404 (16)	0.0456 (18)	−0.0043 (13)	0.0173 (14)	−0.0121 (13)
C14	0.0298 (15)	0.0366 (15)	0.0327 (15)	0.0005 (11)	0.0052 (12)	0.0041 (12)
C15	0.042 (2)	0.083 (3)	0.088 (3)	0.0260 (19)	0.019 (2)	0.043 (2)
C16	0.042 (2)	0.067 (2)	0.123 (4)	0.0193 (18)	0.041 (2)	0.034 (2)
C17	0.0260 (15)	0.0427 (17)	0.060 (2)	0.0015 (12)	0.0165 (14)	0.0078 (14)
C18	0.0455 (18)	0.0397 (16)	0.0545 (19)	−0.0028 (13)	0.0285 (15)	0.0038 (14)
C19	0.063 (2)	0.060 (2)	0.054 (2)	0.0105 (17)	0.0285 (18)	0.0237 (17)
C20	0.055 (2)	0.085 (3)	0.043 (2)	0.0093 (19)	0.0131 (17)	0.0083 (18)
C21	0.052 (2)	0.063 (2)	0.0344 (16)	−0.0132 (16)	0.0162 (15)	−0.0061 (15)

Geometric parameters (Å, º) top

Li—O	1.973 (5)	C8—H8	0.9900
Li—N2ⁱ	1.997 (5)	C9—C10	1.522 (4)
Li—N1	2.057 (5)	C9—H9A	0.9800
Li—N1ⁱ	2.204 (5)	C9—H9B	0.9800
Li—C1ⁱ	2.427 (5)	C10—C11	1.515 (5)
Li—Liⁱ	2.479 (8)	C10—H10A	0.9800
N1—C1	1.355 (3)	C10—H10B	0.9800
N1—C2	1.464 (3)	C11—C12	1.504 (5)
N1—Liⁱ	2.204 (5)	C11—H11A	0.9800
N2—C1	1.314 (3)	C11—H11B	0.9800
N2—C8	1.457 (3)	C12—C13	1.533 (4)
N2—Liⁱ	1.997 (5)	C12—H12A	0.9800
N3—C1	1.413 (3)	C12—H12B	0.9800
N3—C14	1.451 (3)	C13—H13A	0.9800
N3—C17	1.461 (4)	C13—H13B	0.9800
O—C18	1.435 (4)	C14—C15	1.518 (4)
O—C21	1.438 (4)	C14—H14A	0.9800
C1—Liⁱ	2.427 (5)	C14—H14B	0.9800
C2—C7	1.532 (4)	C15—C16	1.489 (6)
C2—C3	1.531 (3)	C15—H15A	0.9800
C2—H2	0.9900	C15—H15B	0.9800
C3—C4	1.528 (4)	C16—C17	1.475 (5)
C3—H3A	0.9800	C16—H16A	0.9800
C3—H3B	0.9800	C16—H16B	0.9800
C4—C5	1.523 (5)	C17—H17A	0.9800
C4—H4A	0.9800	C17—H17B	0.9800
C4—H4B	0.9800	C18—C19	1.507 (5)
C5—C6	1.518 (4)	C18—H18A	0.9800
C5—H5A	0.9800	C18—H18B	0.9800
C5—H5B	0.9800	C19—C20	1.510 (5)
C6—C7	1.530 (4)	C19—H19A	0.9800
C6—H6A	0.9800	C19—H19B	0.9800
C6—H6B	0.9800	C20—C21	1.510 (5)
C7—H7A	0.9800	C20—H20A	0.9800
C7—H7B	0.9800	C20—H20B	0.9800
C8—C9	1.519 (4)	C21—H21A	0.9800
C8—C13	1.529 (4)	C21—H21B	0.9800

O—Li—N2ⁱ	117.1 (2)	C8—C9—C10	112.2 (2)
O—Li—N1	108.7 (2)	C8—C9—H9A	109.2
N2ⁱ—Li—N1	127.9 (2)	C10—C9—H9A	109.2
O—Li—N1ⁱ	122.7 (2)	C8—C9—H9B	109.2
N2ⁱ—Li—N1ⁱ	65.61 (15)	C10—C9—H9B	109.2
N1—Li—N1ⁱ	108.94 (18)	H9A—C9—H9B	107.9
O—Li—C1ⁱ	121.0 (2)	C11—C10—C9	110.6 (3)
N2ⁱ—Li—C1ⁱ	32.77 (10)	C11—C10—H10A	109.5
N1—Li—C1ⁱ	129.0 (2)	C9—C10—H10A	109.5
N1ⁱ—Li—C1ⁱ	33.59 (10)	C11—C10—H10B	109.5
O—Li—Liⁱ	138.3 (3)	C9—C10—H10B	109.5
N2ⁱ—Li—Liⁱ	98.2 (2)	H10A—C10—H10B	108.1
N1—Li—Liⁱ	57.24 (16)	C12—C11—C10	111.2 (3)
N1ⁱ—Li—Liⁱ	51.70 (16)	C12—C11—H11A	109.4
C1ⁱ—Li—Liⁱ	77.4 (2)	C10—C11—H11A	109.4
C1—N1—C2	117.2 (2)	C12—C11—H11B	109.4
C1—N1—Li	126.8 (2)	C10—C11—H11B	109.4
C2—N1—Li	114.63 (19)	H11A—C11—H11B	108.0
C1—N1—Liⁱ	82.27 (18)	C11—C12—C13	112.0 (3)
C2—N1—Liⁱ	133.03 (19)	C11—C12—H12A	109.2
Li—N1—Liⁱ	71.06 (18)	C13—C12—H12A	109.2
C1—N2—C8	120.4 (2)	C11—C12—H12B	109.2
C1—N2—Liⁱ	91.93 (19)	C13—C12—H12B	109.2
C8—N2—Liⁱ	147.6 (2)	H12A—C12—H12B	107.9
C1—N3—C14	124.9 (2)	C12—C13—C8	111.4 (2)
C1—N3—C17	122.0 (2)	C12—C13—H13A	109.3
C14—N3—C17	111.1 (2)	C8—C13—H13A	109.3
C18—O—C21	109.8 (2)	C12—C13—H13B	109.3
C18—O—Li	124.6 (2)	C8—C13—H13B	109.3
C21—O—Li	117.7 (2)	H13A—C13—H13B	108.0
N2—C1—N1	117.6 (2)	N3—C14—C15	104.2 (2)
N2—C1—N3	121.0 (2)	N3—C14—H14A	110.9
N1—C1—N3	121.5 (2)	C15—C14—H14A	110.9
N2—C1—Liⁱ	55.31 (16)	N3—C14—H14B	110.9
N1—C1—Liⁱ	64.14 (16)	C15—C14—H14B	110.9
N3—C1—Liⁱ	165.82 (19)	H14A—C14—H14B	108.9
N1—C2—C7	111.85 (19)	C16—C15—C14	106.5 (3)
N1—C2—C3	111.65 (19)	C16—C15—H15A	110.4
C7—C2—C3	109.3 (2)	C14—C15—H15A	110.4
N1—C2—H2	108.0	C16—C15—H15B	110.4
C7—C2—H2	108.0	C14—C15—H15B	110.4
C3—C2—H2	108.0	H15A—C15—H15B	108.6
C4—C3—C2	111.5 (2)	C17—C16—C15	105.2 (3)
C4—C3—H3A	109.3	C17—C16—H16A	110.7
C2—C3—H3A	109.3	C15—C16—H16A	110.7
C4—C3—H3B	109.3	C17—C16—H16B	110.7
C2—C3—H3B	109.3	C15—C16—H16B	110.7
H3A—C3—H3B	108.0	H16A—C16—H16B	108.8
C5—C4—C3	111.8 (2)	C16—C17—N3	104.4 (3)
C5—C4—H4A	109.2	C16—C17—H17A	110.9
C3—C4—H4A	109.2	N3—C17—H17A	110.9
C5—C4—H4B	109.2	C16—C17—H17B	110.9
C3—C4—H4B	109.2	N3—C17—H17B	110.9
H4A—C4—H4B	107.9	H17A—C17—H17B	108.9
C6—C5—C4	111.0 (2)	O—C18—C19	105.7 (3)
C6—C5—H5A	109.4	O—C18—H18A	110.6
C4—C5—H5A	109.4	C19—C18—H18A	110.6
C6—C5—H5B	109.4	O—C18—H18B	110.6
C4—C5—H5B	109.4	C19—C18—H18B	110.6
H5A—C5—H5B	108.0	H18A—C18—H18B	108.7
C5—C6—C7	112.2 (2)	C20—C19—C18	101.7 (3)
C5—C6—H6A	109.2	C20—C19—H19A	111.4
C7—C6—H6A	109.2	C18—C19—H19A	111.4
C5—C6—H6B	109.2	C20—C19—H19B	111.4
C7—C6—H6B	109.2	C18—C19—H19B	111.4
H6A—C6—H6B	107.9	H19A—C19—H19B	109.3
C6—C7—C2	110.9 (2)	C19—C20—C21	102.8 (3)
C6—C7—H7A	109.5	C19—C20—H20A	111.2
C2—C7—H7A	109.5	C21—C20—H20A	111.2
C6—C7—H7B	109.5	C19—C20—H20B	111.2
C2—C7—H7B	109.5	C21—C20—H20B	111.2
H7A—C7—H7B	108.0	H20A—C20—H20B	109.1
N2—C8—C9	111.0 (2)	O—C21—C20	105.5 (3)
N2—C8—C13	110.6 (2)	O—C21—H21A	110.6
C9—C8—C13	109.0 (2)	C20—C21—H21A	110.6
N2—C8—H8	108.8	O—C21—H21B	110.6
C9—C8—H8	108.8	C20—C21—H21B	110.6
C13—C8—H8	108.8	H21A—C21—H21B	108.8

O—Li—N1—C1	71.7 (3)	C17—N3—C1—Liⁱ	−9.3 (9)
N2ⁱ—Li—N1—C1	−137.6 (3)	C1—N1—C2—C7	104.0 (2)
N1ⁱ—Li—N1—C1	−64.2 (3)	Li—N1—C2—C7	−88.3 (2)
C1ⁱ—Li—N1—C1	−95.4 (3)	Liⁱ—N1—C2—C7	−1.8 (3)
Liⁱ—Li—N1—C1	−64.2 (3)	C1—N1—C2—C3	−133.2 (2)
O—Li—N1—C2	−94.5 (2)	Li—N1—C2—C3	34.5 (3)
N2ⁱ—Li—N1—C2	56.1 (3)	Liⁱ—N1—C2—C3	121.0 (2)
N1ⁱ—Li—N1—C2	129.5 (2)	N1—C2—C3—C4	178.6 (2)
C1ⁱ—Li—N1—C2	98.3 (3)	C7—C2—C3—C4	−57.2 (3)
Liⁱ—Li—N1—C2	129.5 (2)	C2—C3—C4—C5	55.9 (3)
O—Li—N1—Liⁱ	136.0 (3)	C3—C4—C5—C6	−53.3 (4)
N2ⁱ—Li—N1—Liⁱ	−73.4 (3)	C4—C5—C6—C7	53.9 (4)
N1ⁱ—Li—N1—Liⁱ	0.0	C5—C6—C7—C2	−56.6 (3)
C1ⁱ—Li—N1—Liⁱ	−31.19 (16)	N1—C2—C7—C6	−178.7 (2)
N2ⁱ—Li—O—C18	−45.7 (3)	C3—C2—C7—C6	57.2 (3)
N1—Li—O—C18	108.6 (3)	C1—N2—C8—C9	−116.5 (3)
N1ⁱ—Li—O—C18	−122.8 (3)	Liⁱ—N2—C8—C9	58.7 (4)
C1ⁱ—Li—O—C18	−83.0 (3)	C1—N2—C8—C13	122.5 (3)
Liⁱ—Li—O—C18	170.0 (4)	Liⁱ—N2—C8—C13	−62.4 (4)
N2ⁱ—Li—O—C21	168.5 (2)	N2—C8—C9—C10	−179.2 (2)
N1—Li—O—C21	−37.3 (3)	C13—C8—C9—C10	−57.2 (3)
N1ⁱ—Li—O—C21	91.4 (3)	C8—C9—C10—C11	57.5 (3)
C1ⁱ—Li—O—C21	131.1 (3)	C9—C10—C11—C12	−55.1 (3)
Liⁱ—Li—O—C21	24.1 (5)	C10—C11—C12—C13	54.6 (4)
C8—N2—C1—N1	−166.2 (2)	C11—C12—C13—C8	−55.4 (4)
Liⁱ—N2—C1—N1	16.4 (2)	N2—C8—C13—C12	177.7 (2)
C8—N2—C1—N3	13.7 (3)	C9—C8—C13—C12	55.5 (3)
Liⁱ—N2—C1—N3	−163.7 (2)	C1—N3—C14—C15	−159.4 (3)
C8—N2—C1—Liⁱ	177.4 (3)	C17—N3—C14—C15	4.6 (3)
C2—N1—C1—N2	−149.7 (2)	N3—C14—C15—C16	13.9 (4)
Li—N1—C1—N2	44.3 (3)	C14—C15—C16—C17	−27.0 (5)
Liⁱ—N1—C1—N2	−14.9 (2)	C15—C16—C17—N3	29.2 (4)
C2—N1—C1—N3	30.4 (3)	C1—N3—C17—C16	143.2 (3)
Li—N1—C1—N3	−135.6 (2)	C14—N3—C17—C16	−21.4 (4)
Liⁱ—N1—C1—N3	165.1 (2)	C21—O—C18—C19	−14.8 (3)
C2—N1—C1—Liⁱ	−134.8 (2)	Li—O—C18—C19	−162.9 (2)
Li—N1—C1—Liⁱ	59.3 (3)	O—C18—C19—C20	32.7 (3)
C14—N3—C1—N2	−136.5 (3)	C18—C19—C20—C21	−37.6 (3)
C17—N3—C1—N2	61.1 (3)	C18—O—C21—C20	−9.5 (3)
C14—N3—C1—N1	43.4 (4)	Li—O—C21—C20	141.2 (3)
C17—N3—C1—N1	−118.9 (3)	C19—C20—C21—O	29.7 (3)
C14—N3—C1—Liⁱ	153.1 (7)

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Li₂(C₁₇H₃₀N₃)₂(C₄H₈O)₂]
M_r	710.97
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	10.446 (6), 21.454 (15), 10.491 (6)
β (°)	114.13 (4)
V (Å³)	2146 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.980, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	8457, 3688, 2749
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.237, 1.05
No. of reflections	3688
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.61

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

Selected bond lengths (Å) top

Li—O	1.973 (5)	Li—N1	2.057 (5)
Li—N2ⁱ	1.997 (5)	Li—N1ⁱ	2.204 (5)

Symmetry code: (i) −x+2, −y, −z+1.

Acknowledgements

The authors thank Professor Xuehong Wei and the Center of Testing and Analysis, Shanxi University, for support.

References

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