Crystal structure of 1,1',2,2',4,4'-hexa-iso-propyl-magnesocene.

The title compound, 3Cp2Mg or [Mg(C14H23)2], was synthesized from the cor-res-ponding triiso-propyl-cyclo-penta-diene by treatment with n-butyl-sec-butyl-magnesium. The structural characterization by single-crystal X-ray diffraction revealed that the compound crystallizes in the triclinic space group P with half a mol-ecule per asymmetric unit and a staggered arrangement of the cyclo-penta-dienide ligands. © Bachmann et al. 2022.

Chemical context

Magnesocene (Cp2Mg) was initially reported by Wilkinson and Fischer and co-workers in 1954, just a few years after the discovery of ferrocene (Wilkinson & Cotton, 1954 ▸; Fischer & Hafner, 1954 ▸). Although magnesocene exhibits distinctively different chemical properties, it is isostructural to ferrocene and marked the beginning of main-group metallocene chemistry. One of the key differences in reactivity between alkaline-earth metallocenes and ferrocenes is that the central atoms of the former exhibit Lewis acidic character. Therefore, many crystal structures of magnesocenes are actually of donor complexes, such as magnesocene mono- and bis­(tetra­hydro­furan) adduct, Cp2Mg·(thf) and Cp2Mg·(thf)2 (Lehmkuhl et al., 1986 ▸; Jaenschke et al., 2003 ▸; Kim et al., 2007 ▸). Nevertheless, solvent-free crystal structures are also known, especially in case of highly substituted magnesocenes (Morley et al., 1987 ▸; Gardiner et al., 1991 ▸; Weber et al., 2002 ▸; Vollet et al., 2003 ▸; Deacon et al., 2015 ▸; Müller et al., 2021 ▸). Hanusa and coworkers had reported the synthesis of 1,1′,2,2′,4,4′-hexa­iso­propyl­magnesocene, 3Cp2Mg, -calcocene, 3Cp2Ca, -strontocene, 3Cp2Sr, and -barocene, 3Cp2Ba (the triiso­propyl­cyclo­penta­dienide ligand is commonly abbreviated as ‘3Cp’), via treatment of potassium 1,2,4-triiso­propyl­cyclo­penta­dienide, 3CpK, with the corresponding metal(II) bromide or iodide and described the magnesocene to be oily or waxy in composition (Burkey et al., 1993 ▸, 1994 ▸). Thus, no crystal structure was obtained of the title compound. We found that the title compound may also be obtained through treatment of an isomeric mixture of triiso­propyl­cyclo­penta­diene with n-butyl-sec-butyl­magnesium in hexane.

Structural commentary

The title compound crystallizes in the triclinic space group P with half a mol­ecule per asymmetric unit, due to an inversion center at the magnesium atom position (Fig. 1 ▸), resulting in C 2 symmetry for the mol­ecule. Accordingly, the Cp rings adopt a staggered arrangement with the single isopropyl group at the C4 position facing the two isopropyl groups at the C1 and C2 positions and are perfectly coplanar to each other (Fig. 2 ▸). The C—C bond lengths within the Cp ring are almost equal [C1—C2: 1.4237 (18) Å; C2—C3: 1.4268 (17) Å; C3—C4: 1.4172 (19) Å; C4—C5: 1.4220 (18) Å; C5—C1: 1.4277 (18) Å] implying a high degree of 6π electron aromaticity, and the Mg⋯Cpcentroid distance is 1.9852 (1) Å, which is within the normal range [e.g.: Cp2Mg: 1.9897 (5) Å] for magnesocenes (Bünder & Weiss, 1975 ▸).

Figure 1

Asymmetric unit of the title compound (displacement ellipsoids are drawn at the 50% probability level).

Figure 2

(a) Side view and (b) top view of the mol­ecular structure of the title compound in the crystal. Symmetry code: (’) 1 − x, 1 − y, 1 − z. Displacement ellipsoids are drawn at the 50% probability level; H atoms omitted for clarity.

Supra­molecular features

The mol­ecules of the title compound are well separated from each other in the crystal structure, with one magnesocene mol­ecule per unit cell. Each mol­ecule has eight neighboring mol­ecules, forming a distorted hexa­gonal bipyramidal coordination geometry (Fig. 3 ▸ a and 3b), with distances of d min (Mg1⋯Mg1i) = 8.7025 (4) Å, d max (Mg1⋯Mg1iii) = 9.3031 (3) Å and d axial (Mg1⋯Mg1iv) = 9.2033 (4) Å [symmetry codes: (i) −1 + x, y, z; (iii) 1 + x, −1 + y, z; (iv) x, y, 1 + z]. The angles between the equatorial Mg atoms, the central magnesium atom and the axial magnesium atom are between θmin = 90.68° (Mg1iii—Mg1—Mg1iv) and θmax = 99.17° (Mg1ii—Mg1—Mg1iv).

Figure 3

(a) Supra­molecular coordination geometry of the title compound in the crystal and (b) the corresponding polyhedron. Symmetry codes: (i) −1 + x, y, z; (ii) x, −1 + y, z; (iii) 1 + x, −1 + y, z; (iv) x, y, 1 + z. H atoms and isopropyl groups are omitted for clarity.

Each 3Cp2Mg moiety has eight neighboring mol­ecules within the bc and ac planes (Fig. 4 ▸ a and 4b), but only six neighboring mol­ecules within the ab plane, forming an almost hexa­gonal layer (γ = 63.00°), but with the layers being congruent to each other (Fig. 4 ▸ c).

Figure 4

Arrangement of the layers of the title compound along the crystallographic a, b and c axes (H atoms and isopropyl groups omitted for clarity).

Database survey

A search in the Cambridge Structural Database (CSD, Version 5.42, update of September 2021; Groom et al., 2016 ▸) showed that 14 crystal structures of magnesocenes of the type (C5 R 5)2Mg had previously been reported. In this search, any type of donor complexes of magnesocenes of the form (C5 R 5)2Mg· D are not counted. The Mg⋯Cpcentroid bonding distances in these structures lie between 1.9562 (1) and 2.0628 (11) Å and the dihedral angles between the Cp planes are between 0° (co-planar geometry) and 17.892°. Thus, the bond distances and angles in the title compound are within normal ranges of known magnesocenes.

Synthesis and crystallization

Hanusa and coworkers had previously reported that 1,1′,2,2′,4,4′-hexa­iso­propyl­magnesocene, 3Cp2Mg, could be obtained by the reaction of potassium 1,2,4-triiso­propyl­cyclo­penta­dienide with magnesium(II) bromide. However, in this work, we utilized di­butyl­magnesium as a strong base to deprotonate the triiso­propyl­cyclo­penta­diene (Fig. 5 ▸).

Figure 5

Reaction scheme for the formation of the title compound 3Cp2Mg.

To a solution of 4.00 g (20.8 mmol) of an isomeric mixture of triiso­propyl­cyclo­penta­diene in 100 mL of hexane were added 15.0 mL of a 0.7 M solution of n-butyl-sec-butyl­magnesium in hexane (10.5 mmol). The light-yellow reaction solution was stirred at 333 K overnight. Subsequently, all volatiles were removed in vacuo and a yellow oil was obtained, from which the title compound crystallized over the course of one day at ambient temperature. The crystallized material was washed with small portions of hexane and dried in vacuo to obtain the title compound as a pure, colorless, crystalline solid in 43% yield (1.83 g; 4.50 mmol).

In addition to a structural characterization by single-crystal X-ray diffraction, the title compound was also characterized by 1H and 13C NMR spectroscopy: 1H NMR (400 MHz, C6D6, 295 K): δ (in ppm) = 1.07 [d, J = 7Hz, 12H, CH(CH3)2], 1.28 [d, J = 7Hz, 12H, CH(CH3)2], 1.36 [d, J = 7Hz, 12H, CH(CH3)2], 2.82–2.92 [m, 6H, CH(CH3)2], 5.77 (s, 4H, Cp-H); 1H NMR (400 MHz, DMSO-D6, 294 K): δ (in ppm) = 1.06 [d, J = 7Hz, 36H, CH(CH3)2], 2.68 [sep, J = 7Hz, 2H, CH(CH3)2], 2.76 [sep, J = 7Hz, 2H, CH(CH3)2], 4.94 (s, 4H, Cp-H); 13C{1H} NMR (101 MHz, C6D6, 295 K): δ (in ppm) = 24.0 ( Pr), 24.4 ( Pr), 26.4 ( Pr), 26.6 ( Pr), 28.7 ( Pr), 98.7 (Cp), 125.3 (Cp), 128.6 (Cp); 13C{1H} NMR (101 MHz, DMSO-D6, 294 K): δ (in ppm) = 25.9 ( Pr), 26.8 ( Pr), 27.0 ( Pr), 29.1 ( Pr), 94.6 (Cp), 119.4 (Cp), 120.9 (Cp).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1 ▸. All non H-atoms were located in the electron density maps and refined anisotropically. C-bound H atoms were placed in positions of optimized geometry and treated as riding atoms: C—H = 1.00 Å (CH), 0.98 Å (CH3), and with U iso(H) = kU eq(C), where k = 1.2 for CH and 1.5 for CH3.

Table 1

Experimental details

Crystal data
Chemical formula	[Mg(C14H23)2]
M r	406.96
Crystal system, space group	Triclinic, P
Temperature (K)	133
a, b, c (Å)	8.7025 (4), 9.0903 (4), 9.2033 (4)
α, β, γ (°)	80.829 (2), 81.151 (2), 63.004 (1)
V (Å3)	637.68 (5)
Z	1
Radiation type	Mo Kα
μ (mm−1)	0.08
Crystal size (mm)	0.27 × 0.20 × 0.07
Data collection
Diffractometer	Bruker D8 Venture Photon II
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 ▸)
T min, T max	0.712, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	24343, 2808, 2339
R int	0.046
(sin θ/λ)max (Å−1)	0.642
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S	0.041, 0.100, 1.06
No. of reflections	2808
No. of parameters	138
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å−3)	0.23, −0.20

Computer programs: APEX3 and SAINT (Bruker, 2019 ▸), SHELXT2018/2 (Sheldrick, 2015a ▸), SHELXL2018/3 (Sheldrick, 2015b ▸), shelXle (Hübschle et al., 2011 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989022001189/pk2661sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989022001189/pk2661Isup2.hkl

CCDC reference: 2149608

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Mg(C14H23)2]	Z = 1
Mr = 406.96	F(000) = 226
Triclinic, P1	Dx = 1.060 Mg m−3
a = 8.7025 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0903 (4) Å	Cell parameters from 7985 reflections
c = 9.2033 (4) Å	θ = 2.5–27.1°
α = 80.829 (2)°	µ = 0.08 mm−1
β = 81.151 (2)°	T = 133 K
γ = 63.004 (1)°	Plate, yellow
V = 637.68 (5) Å3	0.27 × 0.20 × 0.07 mm

Bruker D8 Venture Photon II diffractometer	2339 reflections with I > 2σ(I)
Radiation source: INCOATEC IµS microfocus sealed tube	Rint = 0.046
φ and ω scans	θmax = 27.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −11→11
Tmin = 0.712, Tmax = 0.746	k = −11→11
24343 measured reflections	l = −11→11
2808 independent reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0357P)2 + 0.2575P] where P = (Fo2 + 2Fc2)/3
2808 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
Mg1	0.500000	0.500000	0.500000	0.02198 (16)
C1	0.58902 (16)	0.29370 (15)	0.34104 (14)	0.0220 (3)
C2	0.68748 (15)	0.38509 (15)	0.29476 (14)	0.0222 (3)
C3	0.78805 (16)	0.36201 (16)	0.41245 (14)	0.0230 (3)
H3	0.876899	0.404101	0.408093	0.028*
C4	0.75424 (15)	0.25725 (15)	0.53102 (14)	0.0223 (3)
C5	0.63013 (16)	0.21621 (15)	0.48667 (14)	0.0232 (3)
H5	0.587559	0.136717	0.544119	0.028*
C6	0.47318 (17)	0.27043 (16)	0.24895 (15)	0.0257 (3)
H6	0.444736	0.359348	0.164188	0.031*
C7	0.30301 (19)	0.2858 (2)	0.33539 (19)	0.0371 (4)
H7A	0.233030	0.269800	0.271125	0.056*
H7B	0.327426	0.201156	0.420434	0.056*
H7C	0.239326	0.396273	0.370110	0.056*
C8	0.5672 (2)	0.10251 (19)	0.18531 (18)	0.0368 (4)
H8A	0.491531	0.091596	0.123487	0.055*
H8B	0.597174	0.012997	0.266371	0.055*
H8C	0.673219	0.095503	0.125346	0.055*
C9	0.69613 (17)	0.47897 (17)	0.14521 (15)	0.0261 (3)
H9	0.585123	0.513065	0.101394	0.031*
C10	0.7151 (2)	0.6358 (2)	0.15456 (18)	0.0422 (4)
H10A	0.719212	0.692389	0.055076	0.063*
H10B	0.822300	0.606089	0.198629	0.063*
H10C	0.615986	0.709829	0.215971	0.063*
C11	0.8434 (2)	0.3681 (2)	0.04173 (17)	0.0401 (4)
H11A	0.843621	0.430001	−0.055715	0.060*
H11B	0.827146	0.270336	0.032239	0.060*
H11C	0.954060	0.332769	0.082140	0.060*
C12	0.82800 (17)	0.20815 (17)	0.68044 (15)	0.0274 (3)
H12	0.750729	0.296459	0.745989	0.033*
C13	1.00801 (19)	0.1994 (2)	0.66748 (18)	0.0408 (4)
H13A	1.087252	0.112649	0.604724	0.061*
H13B	1.049205	0.173474	0.765945	0.061*
H13C	1.003708	0.306602	0.623400	0.061*
C14	0.8308 (3)	0.0458 (2)	0.75386 (19)	0.0463 (4)
H14A	0.712755	0.055338	0.767566	0.069*
H14B	0.876845	0.019984	0.850239	0.069*
H14C	0.904440	−0.043197	0.691324	0.069*

	U11	U22	U33	U12	U13	U23
Mg1	0.0202 (3)	0.0207 (3)	0.0236 (3)	−0.0070 (2)	0.0002 (2)	−0.0067 (2)
C1	0.0213 (6)	0.0189 (6)	0.0243 (6)	−0.0064 (5)	−0.0012 (5)	−0.0066 (5)
C2	0.0195 (6)	0.0222 (6)	0.0227 (6)	−0.0066 (5)	0.0004 (5)	−0.0063 (5)
C3	0.0183 (6)	0.0259 (6)	0.0246 (6)	−0.0088 (5)	−0.0004 (5)	−0.0064 (5)
C4	0.0191 (6)	0.0209 (6)	0.0238 (6)	−0.0049 (5)	−0.0011 (5)	−0.0065 (5)
C5	0.0247 (6)	0.0196 (6)	0.0247 (6)	−0.0089 (5)	−0.0015 (5)	−0.0040 (5)
C6	0.0281 (7)	0.0234 (6)	0.0278 (7)	−0.0116 (5)	−0.0063 (5)	−0.0040 (5)
C7	0.0287 (7)	0.0408 (8)	0.0478 (9)	−0.0168 (6)	−0.0016 (6)	−0.0174 (7)
C8	0.0358 (8)	0.0375 (8)	0.0415 (9)	−0.0151 (7)	−0.0044 (7)	−0.0184 (7)
C9	0.0246 (6)	0.0300 (7)	0.0236 (7)	−0.0123 (5)	−0.0010 (5)	−0.0027 (5)
C10	0.0609 (11)	0.0354 (8)	0.0335 (8)	−0.0274 (8)	0.0068 (7)	−0.0033 (7)
C11	0.0467 (9)	0.0395 (8)	0.0274 (8)	−0.0156 (7)	0.0090 (7)	−0.0075 (6)
C12	0.0268 (7)	0.0270 (6)	0.0246 (7)	−0.0071 (5)	−0.0034 (5)	−0.0059 (5)
C13	0.0298 (8)	0.0566 (10)	0.0338 (8)	−0.0146 (7)	−0.0090 (6)	−0.0067 (7)
C14	0.0652 (11)	0.0427 (9)	0.0356 (9)	−0.0270 (9)	−0.0204 (8)	0.0085 (7)

Mg1—C3i	2.3136 (12)	C7—H7B	0.9800
Mg1—C3	2.3136 (12)	C7—H7C	0.9800
Mg1—C5	2.3148 (12)	C8—H8A	0.9800
Mg1—C5i	2.3148 (12)	C8—H8B	0.9800
Mg1—C4	2.3253 (12)	C8—H8C	0.9800
Mg1—C4i	2.3253 (12)	C9—C11	1.5239 (19)
Mg1—C2i	2.3355 (12)	C9—C10	1.525 (2)
Mg1—C2	2.3355 (12)	C9—H9	1.0000
Mg1—C1i	2.3375 (12)	C10—H10A	0.9800
Mg1—C1	2.3376 (12)	C10—H10B	0.9800
C1—C2	1.4237 (18)	C10—H10C	0.9800
C1—C5	1.4277 (18)	C11—H11A	0.9800
C1—C6	1.5143 (17)	C11—H11B	0.9800
C2—C3	1.4268 (17)	C11—H11C	0.9800
C2—C9	1.5101 (18)	C12—C14	1.514 (2)
C3—C4	1.4172 (19)	C12—C13	1.519 (2)
C3—H3	1.0000	C12—H12	1.0000
C4—C5	1.4220 (18)	C13—H13A	0.9800
C4—C12	1.5226 (18)	C13—H13B	0.9800
C5—H5	1.0000	C13—H13C	0.9800
C6—C7	1.527 (2)	C14—H14A	0.9800
C6—C8	1.5317 (18)	C14—H14B	0.9800
C6—H6	1.0000	C14—H14C	0.9800
C7—H7A	0.9800
C3i—Mg1—C3	180.0	C5—C4—C12	126.88 (12)
C3i—Mg1—C5	121.04 (5)	C3—C4—Mg1	71.76 (7)
C3—Mg1—C5	58.96 (5)	C5—C4—Mg1	71.75 (7)
C3i—Mg1—C5i	58.96 (5)	C12—C4—Mg1	118.67 (8)
C3—Mg1—C5i	121.04 (5)	C4—C5—C1	109.12 (11)
C5—Mg1—C5i	180.0	C4—C5—Mg1	72.56 (7)
C3i—Mg1—C4	144.42 (5)	C1—C5—Mg1	73.00 (7)
C3—Mg1—C4	35.58 (5)	C4—C5—H5	125.3
C5—Mg1—C4	35.69 (4)	C1—C5—H5	125.3
C5i—Mg1—C4	144.31 (4)	Mg1—C5—H5	125.3
C3i—Mg1—C4i	35.58 (5)	C1—C6—C7	112.68 (11)
C3—Mg1—C4i	144.42 (5)	C1—C6—C8	110.81 (11)
C5—Mg1—C4i	144.31 (4)	C7—C6—C8	109.65 (12)
C5i—Mg1—C4i	35.69 (4)	C1—C6—H6	107.8
C4—Mg1—C4i	180.0	C7—C6—H6	107.8
C3i—Mg1—C2i	35.74 (4)	C8—C6—H6	107.8
C3—Mg1—C2i	144.26 (4)	C6—C7—H7A	109.5
C5—Mg1—C2i	120.74 (5)	C6—C7—H7B	109.5
C5i—Mg1—C2i	59.26 (5)	H7A—C7—H7B	109.5
C4—Mg1—C2i	120.27 (4)	C6—C7—H7C	109.5
C4i—Mg1—C2i	59.73 (4)	H7A—C7—H7C	109.5
C3i—Mg1—C2	144.26 (4)	H7B—C7—H7C	109.5
C3—Mg1—C2	35.74 (4)	C6—C8—H8A	109.5
C5—Mg1—C2	59.26 (5)	C6—C8—H8B	109.5
C5i—Mg1—C2	120.74 (5)	H8A—C8—H8B	109.5
C4—Mg1—C2	59.73 (4)	C6—C8—H8C	109.5
C4i—Mg1—C2	120.27 (4)	H8A—C8—H8C	109.5
C2i—Mg1—C2	180.0	H8B—C8—H8C	109.5
C3i—Mg1—C1i	59.17 (4)	C2—C9—C11	110.83 (11)
C3—Mg1—C1i	120.83 (4)	C2—C9—C10	112.69 (11)
C5—Mg1—C1i	144.26 (4)	C11—C9—C10	109.89 (12)
C5i—Mg1—C1i	35.74 (4)	C2—C9—H9	107.7
C4—Mg1—C1i	120.28 (4)	C11—C9—H9	107.7
C4i—Mg1—C1i	59.72 (4)	C10—C9—H9	107.7
C2i—Mg1—C1i	35.48 (4)	C9—C10—H10A	109.5
C2—Mg1—C1i	144.52 (4)	C9—C10—H10B	109.5
C3i—Mg1—C1	120.83 (4)	H10A—C10—H10B	109.5
C3—Mg1—C1	59.17 (4)	C9—C10—H10C	109.5
C5—Mg1—C1	35.74 (4)	H10A—C10—H10C	109.5
C5i—Mg1—C1	144.26 (4)	H10B—C10—H10C	109.5
C4—Mg1—C1	59.72 (4)	C9—C11—H11A	109.5
C4i—Mg1—C1	120.28 (4)	C9—C11—H11B	109.5
C2i—Mg1—C1	144.52 (4)	H11A—C11—H11B	109.5
C2—Mg1—C1	35.48 (4)	C9—C11—H11C	109.5
C1i—Mg1—C1	180.0	H11A—C11—H11C	109.5
C2—C1—C5	107.47 (11)	H11B—C11—H11C	109.5
C2—C1—C6	126.57 (12)	C14—C12—C13	110.23 (13)
C5—C1—C6	125.78 (12)	C14—C12—C4	112.14 (12)
C2—C1—Mg1	72.18 (7)	C13—C12—C4	111.48 (12)
C5—C1—Mg1	71.26 (7)	C14—C12—H12	107.6
C6—C1—Mg1	125.75 (8)	C13—C12—H12	107.6
C1—C2—C3	107.35 (11)	C4—C12—H12	107.6
C1—C2—C9	126.99 (11)	C12—C13—H13A	109.5
C3—C2—C9	125.51 (12)	C12—C13—H13B	109.5
C1—C2—Mg1	72.34 (7)	H13A—C13—H13B	109.5
C3—C2—Mg1	71.29 (7)	C12—C13—H13C	109.5
C9—C2—Mg1	125.19 (8)	H13A—C13—H13C	109.5
C4—C3—C2	109.38 (11)	H13B—C13—H13C	109.5
C4—C3—Mg1	72.66 (7)	C12—C14—H14A	109.5
C2—C3—Mg1	72.97 (7)	C12—C14—H14B	109.5
C4—C3—H3	125.2	H14A—C14—H14B	109.5
C2—C3—H3	125.2	C12—C14—H14C	109.5
Mg1—C3—H3	125.2	H14A—C14—H14C	109.5
C3—C4—C5	106.69 (11)	H14B—C14—H14C	109.5
C3—C4—C12	126.32 (12)
C5—C1—C2—C3	0.18 (13)	C2—C1—C5—C4	−0.49 (13)
C6—C1—C2—C3	−175.17 (11)	C6—C1—C5—C4	174.90 (11)
Mg1—C1—C2—C3	63.12 (8)	Mg1—C1—C5—C4	−64.04 (8)
C5—C1—C2—C9	175.90 (11)	C2—C1—C5—Mg1	63.55 (8)
C6—C1—C2—C9	0.6 (2)	C6—C1—C5—Mg1	−121.06 (12)
Mg1—C1—C2—C9	−121.16 (12)	C2—C1—C6—C7	−138.10 (13)
C5—C1—C2—Mg1	−62.94 (8)	C5—C1—C6—C7	47.38 (17)
C6—C1—C2—Mg1	121.71 (12)	Mg1—C1—C6—C7	−44.39 (16)
C1—C2—C3—C4	0.21 (14)	C2—C1—C6—C8	98.62 (15)
C9—C2—C3—C4	−175.60 (11)	C5—C1—C6—C8	−75.90 (16)
Mg1—C2—C3—C4	64.02 (9)	Mg1—C1—C6—C8	−167.68 (10)
C1—C2—C3—Mg1	−63.81 (8)	C1—C2—C9—C11	−90.94 (15)
C9—C2—C3—Mg1	120.39 (12)	C3—C2—C9—C11	84.04 (16)
C2—C3—C4—C5	−0.50 (13)	Mg1—C2—C9—C11	175.25 (10)
Mg1—C3—C4—C5	63.71 (8)	C1—C2—C9—C10	145.44 (13)
C2—C3—C4—C12	−176.84 (11)	C3—C2—C9—C10	−39.58 (18)
Mg1—C3—C4—C12	−112.63 (12)	Mg1—C2—C9—C10	51.63 (15)
C2—C3—C4—Mg1	−64.21 (8)	C3—C4—C12—C14	−155.61 (13)
C3—C4—C5—C1	0.61 (13)	C5—C4—C12—C14	28.78 (18)
C12—C4—C5—C1	176.92 (11)	Mg1—C4—C12—C14	116.73 (12)
Mg1—C4—C5—C1	64.33 (8)	C3—C4—C12—C13	−31.46 (18)
C3—C4—C5—Mg1	−63.71 (8)	C5—C4—C12—C13	152.93 (13)
C12—C4—C5—Mg1	112.60 (12)	Mg1—C4—C12—C13	−119.13 (11)