Bis(1,2-dimethoxyethane)-1κ2O,O′;3κ2O,O′-tetra­kis­(μ-1,1,1,3,3,3-hexa­fluoro-2-methyl­propan-2-olato)-1:2κ4O:O;2:3κ4O:O-1,3-dilithium-2-magnesium

Wurst, K.; Buchmeiser, M.R.

doi:10.1107/S1600536812032679

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page m1106

https://doi.org/10.1107/S1600536812032679

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Bis(1,2-dimethoxyethane)-1κ²O,O′;3κ²O,O′-tetrakis(μ-1,1,1,3,3,3-hexafluoro-2-methylpropan-2-olato)-1:2κ⁴O:O;2:3κ⁴O:O-1,3-dilithium-2-magnesium

Klaus Wurst ^a and Michael R. Buchmeiser ^b ^*

^aInstitut für Allgemeine und Anorganische und Theoretische Chemie, Universität Innsbruck, Innrain 82, A-6020 Innsbruck, Austria, and ^bLehrstuhl für Makromolekulare Stoffe und Faserchemie, Institut für Polymerchemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
^*Correspondence e-mail: michael.buchmeiser@ipoc.uni-stuttgart.de

(Received 16 July 2012; accepted 18 July 2012; online 25 July 2012)

The title compound, [Li₂Mg(C₄H₃F₆O)₄(C₄H₁₀O₂)₂], forms as a white crystalline powder by-product of the reaction of lithium 1,1,1,3,3,3-hexafluoro-2-methyl-2-propoxide with Mo(N-2,6-Me₂—C₆H₃)(CHCMe₂Ph)(O₃SCF₃)₂·2DME (DME is 1,2-dimethoxyethane) contaminated with MgCl₂. The crystal structure of this compound contains half a molecule in the asymmetric unit, with a twofold rotation axis through the central Mg²⁺ cation. The four 1,1,1,3,3,3-hexafluoro-2-methylpropan-2-olate ligands serve as bridging ligands connecting the Li⁺ and Mg²⁺ cations. The Li⁺ cation is additionally stabilized by a DME ligand. This results in a distorted tetrahedral ligand field around both the Mg²⁺ and Li⁺ cations.

Related literature

For general background on the properties and synthesis of Schrock-type catalysts, see: Oskam et al. (1993 ).

Experimental

Crystal data

[Li₂Mg(C₄H₃F₆O)₄(C₄H₁₀O₂)₂]
M_r = 942.69
Monoclinic, C 2/c
a = 23.8629 (4) Å
b = 9.5396 (6) Å
c = 18.3700 (7) Å
β = 109.041 (2)°
V = 3953.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 233 K
0.41 × 0.25 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer
10600 measured reflections
3490 independent reflections
2603 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.127
S = 1.06
3490 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mg1—O1	1.9526 (14)
Mg1—O2	1.9551 (14)
Li1—O1	1.961 (4)
Li1—O2	1.942 (4)
Li1—O3	1.988 (4)
Li1—O4	2.019 (5)
Mg1⋯Li1	2.818 (4)

O1—Mg1—O1ⁱ	126.14 (10)
O1—Mg1—O2	87.54 (6)
O1—Mg1—O2ⁱ	119.89 (6)
O2—Mg1—O2ⁱ	119.61 (10)
O1—Li1—O2	87.69 (16)
O1—Li1—O3	125.3 (2)
O1—Li1—O4	122.7 (2)
O2—Li1—O3	120.0 (2)
O2—Li1—O4	125.3 (2)
O3—Li1—O4	80.86 (17)
Li1⋯Mg1⋯Li1ⁱ	174.14 (18)
Symmetry code: (i) $[-x, y, -z+{\script{3\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812032679/zl2496sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812032679/zl2496Isup2.hkl

checkCIF report

Comment top

The synthesis of molybdenum-based Schrock-type catalysts involves the reaction of the catalyst progenitor, a Mo–trifluoromethanesulfonate compound such as Mo(N-2,6-Me₂—C₆H₃)(CHCMe₂Ph)(OTf)₂.2DME (OTf = CF₃SO₃^-), with a lithium alkoxide (Oskam et al., 1993), e.g. LiOC(CF₃)₂CH₃, to yield the corresponding Schrock catalyst Mo(N-2,6-Me₂2-C₆H₃)(CHCMe₂Ph)(OC(CF₃)₂CH₃)₂. This reaction step requires high-purity educts in which case the target compounds can be prepared in high yields. However, occasionally, lower yields are observed and could not be explained so far. Here we report on the X-ray structure of a trinuclear Li–Mg compound that forms virtually quantitatively in case the progenitor compound Mo(N-2,6-Me₂—C₆H₃)(CHCMe₂Ph)(OTf)₂.2DME is contaminated with MgCl₂, which is a by-product of the synthesis of this progenitor.

The structure is shown to be a trinuclear complex containing two Li cations and one central Mg cation. Selected geometry parameters are given in Table 1. The two halves of the title compound are related by a twofold axis, which passes through the central magnesium. The Mg atom is coordinated by four η²-bridging Li–1,1,1,3,3,3-hexafluoro-2-methylpropionate ligands that are themselves coordinated to the two Li ions. The latter have each with one 1,2-dimethoxyethane (DME) ligand a distorted tetrahedral ligand sphere. The same distorted tetrahedral ligand sphere exists for the central Mg cation.

In the crystal structure no strong intermolecular hydrogen bonds are present, only F—H distances over 2.47 Å could be observed. Therefore the displacement parameters of the CF₃ groups and the DME ligands are comparatively large, showing a higher mobility of these atoms. An attempt to refine all non-hydrogen atoms of DME with a disordering model by splitting of the positions leads to a better R value, but was rejected because of too short C—O bond lengths. The distances between these split positions were only in the range of 0.28 to 0.46 Å.

Related literature top

For general background on the properties and synthesis of Schrock-type catalysts, see: Oskam et al. (1993).

Experimental top

All reactions were carried out in an MBraun glove box system (Garching, Germany) using carefully dried and deoxygenated solvents. Mo(N-2,6-Me₂—C₆H₃)(CHCMe₂Ph)(OTf)₂.2DME (1) was prepared according to the literature (Oskam et al., 1993). Briefly, ethereal solutions of 1 (1.21 g, contaminated with MgCl₂) and LiOC(CF₃)₂CH₃ (0.62 g, 3.3 mmol) were combined at -36°C and the reaction mixture was allowed to warm to room temperature. Filtration through a pad of Celite and crystallization at -36°C yielded the title complex in 10% yield.

Structure description top

For general background on the properties and synthesis of Schrock-type catalysts, see: Oskam et al. (1993).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (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) and publCIF (Westrip, 2010).

Figures top

Fig. 1. Molecular structure and labeling scheme of the title compound. Ellipsoids are drawn at the 30% probability level. Symmetry code (A): 1 - x, y, 3/2 - z.

Bis(1,2-dimethoxyethane)-1κ²O,O';3κ²O,O'- tetrakis(µ-1,1,1,3,3,3-hexafluoro-2-methylpropan-2-olato)- 1:2κ⁴O:O;2:3κ⁴O:O-1,3-dilithium-2-magnesium top

Crystal data top

[Li₂Mg(C₄H₃F₆O)₄(C₄H₁₀O₂)₂]	F(000) = 1896
M_r = 942.69	D_x = 1.584 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 10988 reflections
a = 23.8629 (4) Å	θ = 1.0–25.0°
b = 9.5396 (6) Å	µ = 0.20 mm⁻¹
c = 18.3700 (7) Å	T = 233 K
β = 109.041 (2)°	Plate, colourless
V = 3953.0 (3) Å³	0.41 × 0.25 × 0.07 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	2603 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
Detector resolution: 9.1 pixels mm^-1	h = 0→28
φ and ω scans	k = −11→11
10600 measured reflections	l = −21→20
3490 independent 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0561P)² + 3.6053P] where P = (F_o² + 2F_c²)/3
3490 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³
0 constraints

Crystal data top

[Li₂Mg(C₄H₃F₆O)₄(C₄H₁₀O₂)₂]	V = 3953.0 (3) Å³
M_r = 942.69	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 23.8629 (4) Å	µ = 0.20 mm⁻¹
b = 9.5396 (6) Å	T = 233 K
c = 18.3700 (7) Å	0.41 × 0.25 × 0.07 mm
β = 109.041 (2)°

Data collection top

Nonius KappaCCD diffractometer	2603 reflections with I > 2σ(I)
10600 measured reflections	R_int = 0.031
3490 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.06	Δρ_max = 0.25 e Å⁻³
3490 reflections	Δρ_min = −0.32 e Å⁻³
271 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
Mg1	0.0000	0.21820 (10)	0.7500	0.0304 (2)
Li1	0.12432 (17)	0.2031 (5)	0.8154 (2)	0.0488 (10)
O1	0.06054 (6)	0.31089 (15)	0.83443 (8)	0.0376 (4)
O2	0.06414 (6)	0.11513 (16)	0.72966 (8)	0.0380 (4)
O3	0.19633 (10)	0.2846 (3)	0.80007 (14)	0.0967 (8)
O4	0.18689 (8)	0.1002 (3)	0.89956 (13)	0.0788 (6)
C1	0.06148 (11)	0.4201 (2)	0.88423 (13)	0.0452 (6)
C2	0.00224 (14)	0.4955 (3)	0.86486 (17)	0.0737 (9)
H2A	−0.0060	0.5439	0.8160	0.111*
H2B	0.0038	0.5629	0.9050	0.111*
H2C	−0.0289	0.4278	0.8612	0.111*
C3	0.10945 (15)	0.5255 (3)	0.88057 (17)	0.0667 (8)
C4	0.07842 (12)	0.3634 (3)	0.96686 (13)	0.0534 (7)
C5	0.06465 (10)	0.0184 (3)	0.67423 (12)	0.0421 (6)
C6	0.00260 (11)	−0.0155 (3)	0.61935 (14)	0.0542 (7)
H6A	0.0054	−0.0857	0.5825	0.081*
H6B	−0.0153	0.0689	0.5922	0.081*
H6C	−0.0216	−0.0512	0.6486	0.081*
C7	0.10204 (12)	0.0747 (3)	0.62675 (15)	0.0596 (7)
C8	0.09244 (12)	−0.1182 (3)	0.71356 (15)	0.0555 (7)
C9	0.24947 (14)	0.2386 (5)	0.8556 (3)	0.1029 (13)
H9A	0.2652	0.3139	0.8929	0.124*
H9B	0.2788	0.2190	0.8300	0.124*
C10	0.24142 (16)	0.1150 (7)	0.8958 (3)	0.1183 (16)
H10A	0.2508	0.0326	0.8700	0.142*
H10B	0.2697	0.1175	0.9483	0.142*
C11	0.2021 (2)	0.3924 (5)	0.7506 (3)	0.1287 (17)
H11A	0.1634	0.4151	0.7144	0.193*
H11B	0.2280	0.3614	0.7226	0.193*
H11C	0.2189	0.4749	0.7807	0.193*
C12	0.17925 (17)	−0.0164 (4)	0.9429 (2)	0.0917 (11)
H12A	0.1382	−0.0216	0.9409	0.138*
H12B	0.2045	−0.0059	0.9960	0.138*
H12C	0.1898	−0.1015	0.9216	0.138*
F1	0.10808 (12)	0.6453 (2)	0.91690 (13)	0.1145 (8)
F2	0.16449 (8)	0.4746 (2)	0.91064 (10)	0.0845 (6)
F3	0.10296 (9)	0.55831 (18)	0.80778 (10)	0.0865 (6)
F4	0.12382 (7)	0.27533 (18)	0.98428 (8)	0.0694 (5)
F5	0.03358 (8)	0.2936 (2)	0.97813 (9)	0.0771 (5)
F6	0.09337 (9)	0.4647 (2)	1.02026 (9)	0.0849 (6)
F7	0.08268 (9)	0.1986 (2)	0.59720 (12)	0.0964 (7)
F8	0.10134 (10)	−0.0077 (3)	0.56813 (11)	0.1073 (8)
F9	0.15870 (7)	0.0932 (2)	0.66710 (11)	0.0895 (6)
F10	0.05962 (9)	−0.17323 (19)	0.75248 (12)	0.0885 (6)
F11	0.14670 (8)	−0.10129 (19)	0.76398 (10)	0.0828 (6)
F12	0.09778 (8)	−0.21737 (18)	0.66513 (11)	0.0857 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mg1	0.0262 (5)	0.0337 (5)	0.0298 (5)	0.000	0.0072 (4)	0.000
Li1	0.033 (2)	0.062 (3)	0.048 (2)	−0.0033 (18)	0.0095 (17)	−0.0061 (19)
O1	0.0339 (8)	0.0390 (9)	0.0359 (8)	−0.0013 (6)	0.0058 (6)	−0.0057 (6)
O2	0.0297 (8)	0.0446 (9)	0.0388 (8)	0.0019 (6)	0.0099 (6)	−0.0085 (7)
O3	0.0595 (15)	0.147 (2)	0.0865 (16)	−0.0383 (14)	0.0279 (12)	0.0027 (15)
O4	0.0418 (12)	0.0969 (17)	0.0879 (15)	0.0052 (10)	0.0077 (10)	0.0001 (13)
C1	0.0489 (14)	0.0404 (13)	0.0406 (12)	0.0023 (11)	0.0066 (10)	−0.0092 (11)
C2	0.073 (2)	0.075 (2)	0.0640 (18)	0.0296 (16)	0.0095 (15)	−0.0161 (15)
C3	0.089 (2)	0.0455 (17)	0.0557 (17)	−0.0132 (15)	0.0098 (15)	−0.0078 (13)
C4	0.0565 (17)	0.0617 (17)	0.0384 (13)	−0.0034 (14)	0.0103 (11)	−0.0119 (12)
C5	0.0365 (13)	0.0509 (14)	0.0392 (12)	0.0032 (10)	0.0129 (9)	−0.0094 (11)
C6	0.0432 (15)	0.0642 (17)	0.0494 (14)	0.0004 (12)	0.0071 (11)	−0.0146 (13)
C7	0.0499 (17)	0.082 (2)	0.0506 (15)	0.0043 (14)	0.0218 (12)	−0.0077 (15)
C8	0.0495 (16)	0.0560 (17)	0.0580 (16)	0.0131 (12)	0.0132 (13)	−0.0126 (13)
C9	0.0324 (18)	0.139 (4)	0.130 (3)	−0.018 (2)	0.0162 (19)	−0.029 (3)
C10	0.046 (2)	0.188 (5)	0.113 (3)	0.004 (3)	0.015 (2)	0.012 (3)
C11	0.125 (4)	0.147 (4)	0.132 (4)	−0.052 (3)	0.067 (3)	0.006 (3)
C12	0.092 (3)	0.098 (3)	0.074 (2)	0.017 (2)	0.0123 (19)	0.013 (2)
F1	0.169 (2)	0.0519 (11)	0.1148 (16)	−0.0323 (13)	0.0355 (15)	−0.0310 (11)
F2	0.0605 (12)	0.1003 (14)	0.0786 (11)	−0.0306 (10)	0.0034 (9)	0.0063 (10)
F3	0.1160 (16)	0.0649 (11)	0.0704 (11)	−0.0227 (10)	0.0192 (10)	0.0165 (9)
F4	0.0675 (11)	0.0814 (11)	0.0496 (9)	0.0126 (9)	0.0058 (7)	0.0119 (8)
F5	0.0748 (12)	0.1057 (14)	0.0553 (9)	−0.0207 (10)	0.0273 (8)	−0.0062 (9)
F6	0.1072 (15)	0.0909 (13)	0.0485 (9)	−0.0129 (11)	0.0143 (9)	−0.0317 (9)
F7	0.0931 (14)	0.1067 (16)	0.1117 (15)	0.0178 (12)	0.0638 (12)	0.0447 (13)
F8	0.1226 (17)	0.1462 (19)	0.0784 (13)	−0.0195 (14)	0.0674 (13)	−0.0434 (13)
F9	0.0449 (10)	0.1405 (18)	0.0897 (13)	−0.0109 (10)	0.0310 (9)	−0.0069 (12)
F10	0.0994 (14)	0.0670 (11)	0.1148 (15)	0.0272 (10)	0.0566 (12)	0.0320 (10)
F11	0.0639 (11)	0.0816 (12)	0.0795 (11)	0.0237 (9)	−0.0085 (9)	−0.0071 (9)
F12	0.0897 (13)	0.0682 (11)	0.0926 (13)	0.0250 (9)	0.0208 (10)	−0.0300 (10)

Geometric parameters (Å, º) top

Mg1—O1	1.9526 (14)	C4—F4	1.325 (3)
Mg1—O1ⁱ	1.9526 (14)	C4—F5	1.333 (3)
Mg1—O2	1.9551 (14)	C4—F6	1.340 (3)
Mg1—O2ⁱ	1.9551 (14)	C5—C6	1.530 (3)
Mg1—Li1	2.818 (4)	C5—C8	1.532 (4)
Mg1—Li1ⁱ	2.818 (4)	C5—C7	1.534 (4)
Li1—O1	1.961 (4)	C6—H6A	0.9700
Li1—O2	1.942 (4)	C6—H6B	0.9700
Li1—O3	1.988 (4)	C6—H6C	0.9700
Li1—O4	2.019 (5)	C7—F7	1.319 (3)
Mg1—Li1	2.818 (4)	C7—F9	1.325 (3)
O1—C1	1.382 (3)	C7—F8	1.329 (3)
O2—C5	1.377 (3)	C8—F10	1.329 (3)
O3—C11	1.409 (5)	C8—F12	1.333 (3)
O3—C9	1.413 (5)	C8—F11	1.333 (3)
O4—C10	1.333 (4)	C9—C10	1.437 (7)
O4—C12	1.414 (4)	C9—H9A	0.9800
C1—C2	1.522 (4)	C9—H9B	0.9800
C1—C4	1.536 (3)	C10—H10A	0.9800
C1—C3	1.541 (4)	C10—H10B	0.9800
C2—H2A	0.9700	C11—H11A	0.9700
C2—H2B	0.9700	C11—H11B	0.9700
C2—H2C	0.9700	C11—H11C	0.9700
C3—F1	1.329 (3)	C12—H12A	0.9700
C3—F3	1.332 (3)	C12—H12B	0.9700
C3—F2	1.339 (4)	C12—H12C	0.9700

O1—Mg1—O1ⁱ	126.14 (10)	F4—C4—F5	106.2 (2)
O1—Mg1—O2	87.54 (6)	F4—C4—F6	106.2 (2)
O1ⁱ—Mg1—O2	119.89 (6)	F5—C4—F6	106.4 (2)
O1—Mg1—O2ⁱ	119.89 (6)	F4—C4—C1	113.1 (2)
O1ⁱ—Mg1—O2ⁱ	87.54 (6)	F5—C4—C1	111.3 (2)
O2—Mg1—O2ⁱ	119.61 (10)	F6—C4—C1	113.0 (2)
O1—Mg1—Li1	44.06 (9)	O2—C5—C6	112.89 (18)
O1ⁱ—Mg1—Li1	139.90 (10)	O2—C5—C8	109.16 (18)
O2—Mg1—Li1	43.50 (9)	C6—C5—C8	107.9 (2)
O2ⁱ—Mg1—Li1	132.37 (10)	O2—C5—C7	109.4 (2)
O1—Mg1—Li1ⁱ	139.90 (10)	C6—C5—C7	108.5 (2)
O1ⁱ—Mg1—Li1ⁱ	44.06 (9)	C8—C5—C7	108.9 (2)
O2—Mg1—Li1ⁱ	132.37 (10)	C5—C6—H6A	109.5
O2ⁱ—Mg1—Li1ⁱ	43.50 (9)	C5—C6—H6B	109.5
O1—Li1—O2	87.69 (16)	H6A—C6—H6B	109.5
O1—Li1—O3	125.3 (2)	C5—C6—H6C	109.5
O1—Li1—O4	122.7 (2)	H6A—C6—H6C	109.5
O2—Li1—O3	120.0 (2)	H6B—C6—H6C	109.5
O2—Li1—O4	125.3 (2)	F7—C7—F9	105.5 (3)
O3—Li1—O4	80.86 (17)	F7—C7—F8	106.6 (2)
Li1—Mg1—Li1ⁱ	174.14 (18)	F9—C7—F8	105.8 (2)
O2—Li1—Mg1	43.88 (9)	F7—C7—C5	110.9 (2)
O1—Li1—Mg1	43.83 (9)	F9—C7—C5	113.9 (2)
O3—Li1—Mg1	139.3 (2)	F8—C7—C5	113.4 (2)
O4—Li1—Mg1	139.8 (2)	F10—C8—F12	106.3 (2)
C1—O1—Mg1	135.67 (14)	F10—C8—F11	106.5 (2)
C1—O1—Li1	131.90 (18)	F12—C8—F11	105.5 (2)
Mg1—O1—Li1	92.11 (13)	F10—C8—C5	110.5 (2)
C5—O2—Li1	134.95 (17)	F12—C8—C5	114.2 (2)
C5—O2—Mg1	132.43 (13)	F11—C8—C5	113.4 (2)
Li1—O2—Mg1	92.62 (13)	O3—C9—C10	112.7 (3)
C11—O3—C9	116.0 (3)	O3—C9—H9A	109.0
C11—O3—Li1	130.4 (3)	C10—C9—H9A	109.0
C9—O3—Li1	113.0 (3)	O3—C9—H9B	109.0
C10—O4—C12	114.8 (3)	C10—C9—H9B	109.0
C10—O4—Li1	113.5 (3)	H9A—C9—H9B	107.8
C12—O4—Li1	127.9 (2)	O4—C10—C9	114.2 (4)
O1—C1—C2	112.9 (2)	O4—C10—H10A	108.7
O1—C1—C4	109.35 (19)	C9—C10—H10A	108.7
C2—C1—C4	108.8 (2)	O4—C10—H10B	108.7
O1—C1—C3	108.3 (2)	C9—C10—H10B	108.7
C2—C1—C3	109.1 (2)	H10A—C10—H10B	107.6
C4—C1—C3	108.2 (2)	O3—C11—H11A	109.5
C1—C2—H2A	109.5	O3—C11—H11B	109.5
C1—C2—H2B	109.5	H11A—C11—H11B	109.5
H2A—C2—H2B	109.5	O3—C11—H11C	109.5
C1—C2—H2C	109.5	H11A—C11—H11C	109.5
H2A—C2—H2C	109.5	H11B—C11—H11C	109.5
H2B—C2—H2C	109.5	O4—C12—H12A	109.5
F1—C3—F3	106.7 (2)	O4—C12—H12B	109.5
F1—C3—F2	106.6 (2)	H12A—C12—H12B	109.5
F3—C3—F2	106.1 (3)	O4—C12—H12C	109.5
F1—C3—C1	113.5 (3)	H12A—C12—H12C	109.5
F3—C3—C1	110.6 (2)	H12B—C12—H12C	109.5
F2—C3—C1	112.8 (2)

O1—Mg1—Li1—O2	−177.8 (2)	O2—Li1—O4—C12	−47.5 (4)
O1ⁱ—Mg1—Li1—O2	−82.68 (18)	O1—Li1—O4—C12	65.9 (4)
O2ⁱ—Mg1—Li1—O2	90.60 (17)	O3—Li1—O4—C12	−167.8 (3)
O1ⁱ—Mg1—Li1—O1	95.15 (18)	Mg1—Li1—O4—C12	10.5 (5)
O2—Mg1—Li1—O1	177.8 (2)	Mg1—O1—C1—C2	−6.4 (3)
O2ⁱ—Mg1—Li1—O1	−91.57 (15)	Li1—O1—C1—C2	165.2 (2)
O1—Mg1—Li1—O3	−93.8 (3)	Mg1—O1—C1—C4	114.8 (2)
O1ⁱ—Mg1—Li1—O3	1.3 (4)	Li1—O1—C1—C4	−73.6 (3)
O2—Mg1—Li1—O3	84.0 (3)	Mg1—O1—C1—C3	−127.4 (2)
O2ⁱ—Mg1—Li1—O3	174.6 (2)	Li1—O1—C1—C3	44.2 (3)
O1—Mg1—Li1—O4	88.7 (3)	O1—C1—C3—F1	170.0 (2)
O1ⁱ—Mg1—Li1—O4	−176.1 (2)	C2—C1—C3—F1	46.8 (3)
O2—Mg1—Li1—O4	−93.5 (3)	C4—C1—C3—F1	−71.5 (3)
O2ⁱ—Mg1—Li1—O4	−2.9 (4)	O1—C1—C3—F3	50.1 (3)
O1ⁱ—Mg1—O1—C1	46.36 (19)	C2—C1—C3—F3	−73.1 (3)
O2—Mg1—O1—C1	172.3 (2)	C4—C1—C3—F3	168.6 (2)
O2ⁱ—Mg1—O1—C1	−64.7 (2)	O1—C1—C3—F2	−68.5 (3)
Li1—Mg1—O1—C1	173.8 (3)	C2—C1—C3—F2	168.2 (2)
Li1ⁱ—Mg1—O1—C1	−12.7 (3)	C4—C1—C3—F2	50.0 (3)
O1ⁱ—Mg1—O1—Li1	−127.40 (14)	O1—C1—C4—F4	45.1 (3)
O2—Mg1—O1—Li1	−1.49 (14)	C2—C1—C4—F4	168.8 (2)
O2ⁱ—Mg1—O1—Li1	121.59 (14)	C3—C1—C4—F4	−72.8 (3)
Li1ⁱ—Mg1—O1—Li1	173.5 (2)	O1—C1—C4—F5	−74.5 (3)
O2—Li1—O1—C1	−172.63 (19)	C2—C1—C4—F5	49.2 (3)
O3—Li1—O1—C1	−46.9 (4)	C3—C1—C4—F5	167.7 (2)
O4—Li1—O1—C1	56.0 (4)	O1—C1—C4—F6	165.8 (2)
Mg1—Li1—O1—C1	−174.1 (2)	C2—C1—C4—F6	−70.5 (3)
O2—Li1—O1—Mg1	1.51 (14)	C3—C1—C4—F6	48.0 (3)
O3—Li1—O1—Mg1	127.2 (2)	Li1—O2—C5—C6	179.6 (2)
O4—Li1—O1—Mg1	−129.9 (2)	Mg1—O2—C5—C6	−1.2 (3)
O1—Li1—O2—C5	177.9 (2)	Li1—O2—C5—C8	59.6 (3)
O3—Li1—O2—C5	47.8 (4)	Mg1—O2—C5—C8	−121.24 (19)
O4—Li1—O2—C5	−52.7 (4)	Li1—O2—C5—C7	−59.5 (3)
Mg1—Li1—O2—C5	179.4 (3)	Mg1—O2—C5—C7	119.70 (19)
O1—Li1—O2—Mg1	−1.50 (14)	O2—C5—C7—F7	−55.3 (3)
O3—Li1—O2—Mg1	−131.6 (2)	C6—C5—C7—F7	68.2 (3)
O4—Li1—O2—Mg1	127.9 (2)	C8—C5—C7—F7	−174.6 (2)
O1—Mg1—O2—C5	−177.90 (19)	O2—C5—C7—F9	63.5 (3)
O1ⁱ—Mg1—O2—C5	−46.9 (2)	C6—C5—C7—F9	−172.9 (2)
O2ⁱ—Mg1—O2—C5	58.78 (18)	C8—C5—C7—F9	−55.7 (3)
Li1—Mg1—O2—C5	−179.4 (3)	O2—C5—C7—F8	−175.3 (2)
Li1ⁱ—Mg1—O2—C5	6.4 (2)	C6—C5—C7—F8	−51.7 (3)
O1—Mg1—O2—Li1	1.51 (14)	C8—C5—C7—F8	65.5 (3)
O1ⁱ—Mg1—O2—Li1	132.53 (14)	O2—C5—C8—F10	63.4 (3)
O2ⁱ—Mg1—O2—Li1	−121.82 (14)	C6—C5—C8—F10	−59.7 (3)
Li1ⁱ—Mg1—O2—Li1	−174.16 (18)	C7—C5—C8—F10	−177.2 (2)
O2—Li1—O3—C11	60.1 (5)	O2—C5—C8—F12	−176.9 (2)
O1—Li1—O3—C11	−50.4 (5)	C6—C5—C8—F12	60.0 (3)
O4—Li1—O3—C11	−174.3 (4)	C7—C5—C8—F12	−57.5 (3)
Mg1—Li1—O3—C11	7.4 (5)	O2—C5—C8—F11	−56.0 (3)
O2—Li1—O3—C9	−129.6 (3)	C6—C5—C8—F11	−179.1 (2)
O1—Li1—O3—C9	119.9 (3)	C7—C5—C8—F11	63.4 (3)
O4—Li1—O3—C9	−4.0 (3)	C11—O3—C9—C10	−171.0 (4)
Mg1—Li1—O3—C9	177.7 (3)	Li1—O3—C9—C10	17.2 (5)
O2—Li1—O4—C10	109.4 (4)	C12—O4—C10—C9	−176.4 (4)
O1—Li1—O4—C10	−137.2 (3)	Li1—O4—C10—C9	23.6 (5)
O3—Li1—O4—C10	−10.9 (3)	O3—C9—C10—O4	−27.0 (6)
Mg1—Li1—O4—C10	167.4 (4)

Symmetry code: (i) −x, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Li₂Mg(C₄H₃F₆O)₄(C₄H₁₀O₂)₂]
M_r	942.69
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	233
a, b, c (Å)	23.8629 (4), 9.5396 (6), 18.3700 (7)
β (°)	109.041 (2)
V (Å³)	3953.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.41 × 0.25 × 0.07

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10600, 3490, 2603
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.127, 1.06
No. of reflections	3490
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.32

Computer programs: COLLECT (Nonius, 1998), DENZO-SMN (Otwinowski & Minor, 1997), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Mg1—O1	1.9526 (14)	Li1—O3	1.988 (4)
Mg1—O2	1.9551 (14)	Li1—O4	2.019 (5)
Li1—O1	1.961 (4)	Mg1—Li1	2.818 (4)
Li1—O2	1.942 (4)

O1—Mg1—O1ⁱ	126.14 (10)	O1—Li1—O4	122.7 (2)
O1—Mg1—O2	87.54 (6)	O2—Li1—O3	120.0 (2)
O1—Mg1—O2ⁱ	119.89 (6)	O2—Li1—O4	125.3 (2)
O2—Mg1—O2ⁱ	119.61 (10)	O3—Li1—O4	80.86 (17)
O1—Li1—O2	87.69 (16)	Li1—Mg1—Li1ⁱ	174.14 (18)
O1—Li1—O3	125.3 (2)

Symmetry code: (i) −x, y, −z+3/2.

Acknowledgements

Financial support provided by the DFG (BU 2174/8-1) is gratefully acknowledged. The authors thank S. P. Westrip and the IUCr for the development of publCIF.

References

Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Oskam, J. H., Fox, H. H., Yap, K. B., McConville, D. H., O'Dell, R., Lichtenstein, B. J. & Schrock, R. R. (1993). J. Organomet. Chem. 459, 185–197. CrossRef CAS Web of Science Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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