Crystal structure of bis­(μ2-meth­anolato-κO:κO)hexa­methyl­bis­(μ2-tri­phenyl­acetato-κO:κO′)bis­(μ2-tri­phenyl­acetato-κ2O,O′:κO)dialuminiumdi­lanthanum toluene tetra­solvate

Vinogradov, A.A.; Roitershtein, D.M.; Minyaev, M.E.; Lyssenko, K.A.; Nifant'ev, I.E.

doi:10.1107/S2056989018015876

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ISSN: 2056-9890

Volume 74| Part 12| December 2018| Pages 1790-1794

https://doi.org/10.1107/S2056989018015876

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Crystal structure of bis(μ₂-methanolato-κO:κO)hexamethylbis(μ₂-triphenylacetato-κO:κO′)bis(μ₂-triphenylacetato-κ²O,O′:κO)dialuminiumdilanthanum toluene tetrasolvate

Alexander A. Vinogradov,^a Dmitrii M. Roitershtein,^a,^b Mikhail E. Minyaev,^a ^* Konstantin A. Lyssenko ^c and Ilya E. Nifant'ev ^a,^d

^aA.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky Prospect, 119991, Moscow, Russian Federation, ^bN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, 119991, Russian Federation, ^cA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova Str., 119991, Moscow, Russian Federation, and ^dChemistry Department, M.V. Lomonosov Moscow State, University, 1 Leninskie Gory Str., Building 3, Moscow 119991, Russian Federation
^*Correspondence e-mail: mminyaev@mail.ru

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 29 October 2018; accepted 8 November 2018; online 13 November 2018)

The title compound, [Al₂La₂(C₂₀H₁₅O₂)₄(CH₃)₆(CH₃O)₂]·4CH₃C₆H₅ or [{La(Ph₃CCOO)₂(Me₃AlOMe)}₂]·4CH₃C₆H₅, was formed in a reaction between lanthanum tris(tetramethylaluminate) and triphenylacetic acid (1:1) with unintended partial oxidation. The triphenylacetate ligand exhibits μ₂-κ¹O:κ¹O′ bridging and μ₂-κ²O,O′:κ¹O semi-bridging coordination modes, forming a dimeric La₂(μ-OCO)₄ core. The semi-bridging triphenylacetate group provides additional bonding with an La³⁺ cation via the π-system of one of its phenyl rings. The trimethylmethoxyaluminate anion, which is coordinated to the La³⁺ cation by its O atom, displays a rather long La—C_Me bond. Two toluene molecules are each disordered over two orientations about centres of symmetry with site occupancy factors of 0.5. The title compound represents the first example of an Ln^III complex containing both alkyl alkoxide aluminate and π-bounded arene fragments.

Keywords: lanthanum; aluminium; triphenylacetate; π-complex; coordination compound; crystal structure.

CCDC reference: 1877930

1. Chemical context

Heteroleptic tetraalkylaluminate complexes of rare-earth metals attract significant attention because of their intriguing role in the stereospecific polymerization of conjugated dienes (Anwander, 2002 ). Stereoregular elastomers obtained in the polymerization process of isoprene and butadiene are fundamentally important for the production of modern wear-resistant rubbers (Friebe et al., 2006 ). It is assumed that this type of complex plays the key role in the formation of catalytically active species. Meanwhile, little is known about the structure of such complexes (Fischbach et al., 2006a , and reference therein). The exceptionally high oxidative instability of aluminate complexes is one of the reasons for the lack of information on the structures of catalytically active heteroleptic bimetallic Ln–Al complexes.

This report describes the product of unintentional oxidation of a carboxylate–aluminate La complex while reacting lanthanum tris(tetramethylaluminiumate) with the corresponding acid (Fig. 1). This reaction should have led initially to the heteroleptic triphenylacetate–tetramethylaluminate complex that is supposed to be a model of the active species in the catalyst system. The accidental partial oxidation resulted in the formation of the triphenylacetate-trimethylmethoxyaluminate lanthanum complex [{La(Ph₃CCOO)₂Me₃AlOMe}₂].

Figure 1
Synthesis of [{La(Ph₃CCOO)₂Me₃AlOMe}₂]·4(CH₃C₆H₅).

2. Structural commentary

The asymmetric unit of the title compound consists of half of the dimeric complex [{La(Ph₃CCOO)₂(Me₃AlOMe)}₂] (Fig. 2) located on an inversion centre, and three non-coordinating toluene molecules (not shown). Two of the toluene molecules are disordered over inversion centres, having 50% atomic site occupancies. The coordination polyhedron for the La³⁺ cation and its coordination number are rather difficult to determine. Two triphenylacetate ligands exhibit the μ₂-κ¹O:κ¹O′ bridging coordination mode, but two other ligands display the μ₂-κ²O,O′:κ¹O′ semi-bridging type (Figs. 2 and 3; Table 1). The complex has an La₂(μ-OCO)₄ core with an La1⋯La1ⁱ distance of 4.0432 (4) Å [symmetry code: (i) −x, −y + 1, −z + 1). Unlike the bridging ligands, the semi-bridging triphenylacetates demonstrate additional La⋯C contacts with the carboxylic system (La1⋯C5, La1ⁱ⋯C5ⁱ; Fig. 3; Table 1). The La³⁺ cation is also coordinated by the π-system of a phenyl ring of the semi-bridging carboxylate ligand (Fig. 3, atoms C7ⁱ–C12ⁱ; Table 1). The interaction with the phenyl (Ph) group is close to symmetrical: the La⋯Ph_centroid distance is 2.938 (2) Å, the normal to the Ph-ring plane is 2.9353 (16) Å, and the La⋯C_Ph bond lengths lie in the range 3.201 (4) to 3.318 (4) Å. Ten crystal structures exhibiting the interaction of La³⁺ with the π-system of an uncharged C₆ aromatic ring have been found in the Cambridge Structural Database (CSD, Version 5.39, February 2018 update; Groom et al., 2016 ). The corresponding distances in these compounds vary from 2.93 to 3.27 Å for La⋯C_Aryl and from 2.61 to 2.87 Å for La⋯Aryl_centroid. The La⋯Ph_centroid and La⋯C_Ph distances in the title compound are therefore the longest, which is likely caused by steric hindrance induced by the presence of many phenyl groups within the inner coordination sphere.

Table 1
Selected bond lengths (Å)

La1—O1	2.336 (3)	La1—C8ⁱ	3.287 (4)
La1—O2	2.501 (3)	La1—C9ⁱ	3.246 (4)
La1—O3	2.494 (3)	La1—C10ⁱ	3.212 (4)
La1—O3ⁱ	2.403 (2)	La1—C11ⁱ	3.201 (4)
La1—O4	2.396 (3)	La1—C12ⁱ	3.239 (4)
La1—O5ⁱ	2.367 (3)	Al1—O1	1.819 (3)
La1—C2	3.042 (4)	Al1—C2	2.014 (4)
La1—C5	2.892 (4)	Al1—C3	1.990 (5)
La1—C7ⁱ	3.318 (4)	Al1—C4	1.961 (4)
Symmetry code: (i) -x, -y+1, -z+1.

Figure 2
The molecular structure of the {La(Ph₃CCOO)₂(Me₃AlOMe)}₂ unit in the title compound with displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms and toluene solvent molecules are omitted for clarity. The La—O bonds are shown with thinner solid lines. The La—C interactions are not shown. Symmetry code: (i) −x, −y + 1, −z + 1.

Figure 3
Metal–ligand interactions within the {La(Ph₃CCOO)₂(Me₃AlOMe)}₂ unit. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted, only C_ipso atoms (labeled as Ph) are shown for non-coordinating phenyl groups for clarity. The Ln—C contacts are shown with thin dashed lines. Symmetry code: (i) −x, −y + 1, −z + 1.

The trimethylmetoxyaluminate anions are coordinated to the La³⁺ cations via oxygen atoms (La1—O1, La1ⁱ—O1ⁱ), and exhibit a slightly distorted tetrahedral environment about the Al atoms, with an O1—Al1—C2 angle of 100.03 (17)° and with other O—Al—C and C—Al—C bond angles ranging from 108.32 (18) to 113.2 (2)°. The small value for the O1—Al1—C2 angle is due to the additional coordination of the [Al(CH₃)₃(OCH₃)] anion with La³⁺ by the C2 atom (Fig. 3). However, the La1—C2 bond length [3.042 (4) Å] is rather long compared to those of previously characterized compounds possessing the La–[(μ-Me)₂AlMe₂] fragment, which have La—C_Me distances lying in the range 2.66 to 2.98 Å with the average value of 2.76 Å (32 compounds with 128 crystallographically independent La—C_Me-Al distances retrieved from the CSD). The La1⋯Al1 distance [3.4481 (12) Å] is near to the upper boundary of the La—Al distance range in the aforementioned compounds (from 2.99 to 3.45 Å, with an average of 3.25 Å).

There is only one related compound having the La-[(Alkyl/Aryl)₃Al(OAlkyl/OAryl)] motif (CSD refcode MIMPED; Giesbrecht et al., 2002 ) – {La(O-2,6-ⁱPr₂C₆H₃)[AlMe₂(μ-Me)(μ-O-2,6-ⁱPr₂C₆H₃)]₂}. The Al—O [1.864 (3), 1.848 (3) Å], La—O [2.387 (3), 2.367 (3) Å] and Al—C [2.040 (5), 2.053 (6) Å] bond lengths within the LaAl₂(μ-Me)₂(μ-OAryl)₂ fragment are similar to those found in the LaAl(μ-Me)(μ-OMe) fragment of the complex reported herein. However, the La1—C2 distance in the title compound (Table 1) is considerably longer (by 0.24-0.28 Å) than the corresponding La—C distances in MIMPED [2.800 (5), 2.759 (5) Å], presumably due to steric reasons.

In the studied compound, the La—O_Me (La1—O1) bond is the shortest, compared to the other La—O bonds, which may be due to delocalization of negative charge on the carboxy oxygen atoms and/or steric repulsion of the bulky carboxylate anion.

3. Supramolecular features

Weak intra- and intermolecular interactions among complex molecules and non-coordinating toluene molecules are mainly represented by the C_Ph—H··π type (Table 2). An interesting feature of the crystal packing is that the centres of all non-coordinating toluene molecules are located nearly in one plane parallel to the ab plane, separating 2D molecular layers of the complex (Fig. 4).

Table 2
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C33–C38, C39–C44, C52–C57 and C19–C24 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯⋯Cg1ⁱ	0.98	2.69	3.425 (6)	132
C17—H17⋯⋯Cg2	0.95	2.71	3.485 (4)	139
C21—H21⋯⋯Cg3ⁱⁱ	0.95	2.93	3.677 (8)	136
C29—H29⋯⋯Cg4	0.95	2.62	3.415 (4)	142
C32—H32⋯⋯Cg2	0.95	2.95	3.654 (5)	132
C44—H44⋯⋯Cg1	0.95	2.88	3.592 (5)	132
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y, -z+1.

Figure 4
A view along the b axis of the crystal packing of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted.

4. Database survey

The number of crystal structures for rare-earth compounds containing the Ln–C–Al fragment (CSD, Version 5.39, February 2018 update; Groom et al., 2016) is nearly 250 (upon exclusion of duplicated structures). They are mainly represented by 147 tetramethylaluminates with Ln-[(μ₂-Me)₂AlMe₂] (127 structures), Ln-[(μ₂-Me)AlMe₂(μ₂-Me)]-Ln (11 structures) and Ln-[(μ₂-Me)AlMe₃] (9 structures) fragments and by 16 tetraethylaluminate complexes. This number also includes 18 structures of Ln-[(Alkyl/Aryl)₃Al(OAlkyl/OAryl) compounds possessing the following structural motifs: [(μ₂-Me)(μ₂-OCH₂^tBu)AlMe₂] (AVOYOA, AVOYUG, Occhipinti et al., 2011 ; GEQMOF, GEQMUL, Fischbach et al., 2006b ), [(μ₂-Me)(μ₂-O^tBu)AlMe₂] (POJNAD, Biagini et al., 1994 ; WAPYIV, WAPYOB, Evans et al., 1993a ; WEHHAS, Evans et al., 1993b ), [(μ₂-Me)(μ₂-OⁱPr)AlMe₂] (VOLMUF, Liu et al., 2005 ), [(μ₂-Me)(μ₂-O-2,6-Ph₂C₆H₃)AlMe₂] (TULCAF, Korobkov & Gambarotta, 2009 ), [(μ₂-Me)(μ₂-O-2,6-ⁱPr₂C₆H₃)AlMe₂] (LUQZOM, Fischbach et al., 2003 ; MIMPED, Giesbrecht et al., 2002; MOQYOG, Gordon et al., 2002 ; PETMUX, Fischbach et al., 2006c ), [(μ₂-Et)(μ₂-O-2,6-ⁱPr₂C₆H₃)AlEt₂] (MIMPIH, Giesbrecht et al., 2002; ROCHOH, Sommerfeldt et al., 2008 ), [(μ₂-Me)(μ₂-O-2,6-^tBu₂-4-MeC₆H₂)AlMe₂] (ROCGOG, Sommerfeldt et al., 2008), [(κ²O,O′-MeOCH₂CH₂O)AlMe₃] (GIZWAN, Evans et al., 1998 ). MIMPED is the only La structure among them. A related structure with the {(μ₂-Me)[μ₂-κO:κ²O,O′-(O^tBu)₃SiO]AlMe₂} motif (BEQXUR, Fischbach et al., 2004 ) might be also mentioned.

Crystal structures of lanthanide(III) compounds having an η⁶-coordinated uncharged arene system have become numerous over the last two decades, resulting in the description of over 150 crystal structures (see the CSD). Ten structures of such La(III) π-complexes are known: EZIPIM (Giesbrecht et al., 2004 ), MALXOM (Deacon et al., 2000 ), POKCAU (Gerber et al., 2008 ), RILBIZ, RILBUL (Hamidi et al., 2013 ), ROMQUG (Filatov et al., 2009 ), SOJHAB, SOJHEF, SOJHIJ (Filatov et al., 2008 ), ZIDSOV (Butcher et al., 1995 ). Crystallographic data for these complexes were used to compare structural parameters of the title compound in the Structural Commentary section. Known crystal structures of rare-earth triphenylacetate complexes are also not numerous, and their number is limited to 16 recent crystal structures: peroxide bis(triphenylacetate) complexes QEHBOX, QEHBUD, QEHCEO (Roitershtein et al., 2017 ), mono- and binuclear tris(triphenylacetate) complexes EPUNIO (Minyaev et al., 2016 ), RIKRIO, RIKRUA, RIKSAH, RIKSEL (Roitershtein et al., 2013 ), tetrakis(triphenylacetate) complexes and their adducts RIKQUZ, RIKRAG, RIKREK, RIKRIO (Roitershtein et al., 2013), triphenylacetate-tetraethylaluminate compounds RIJVIR, RIJVOX (Roitershtein et al., 2013) and heptanuclear polyligand complexes UVETAR, UVETEV (Sharples et al., 2011 ). The triphenylacetate ligand exhibits terminal κO and κ²O,O′, bridging μ-κO,κO′, and semi-bridging μ-κO,κ²O,O′ (the latter is only for the four ate complexes) coordination modes.

Up to date, no complex has been reported that has both an η⁶-coordinated arene ligand and the mixed-ligand alkyl-alkoxide aluminate anion.

5. Synthesis and crystallization

Synthetic operations were carried out under a purified argon atmosphere. Toluene was distilled from sodium/benzophenone ketyl, hexane was distilled from Na/K alloy. Triphenylacetic acid was purified by azeotrope removal of water from its toluene solution with a Dean–Stark trap, followed by crystallization from a cold saturated solution and then by vacuum drying. The complex La(AlMe₄)₃ was prepared according to the literature procedure (Zimmermann et al., 2007 ).

A solution of Ph₃CCOOH (0.144 g, 0.50 mmol) in toluene (20 ml) was added to a stirred solution of La(AlMe₄)₃ (0.196 g, 0.49 mmol) in toluene (10 ml), producing a suspension, which was stirred overnight at room temperature. The precipitate was removed by decantation and the solution was concentrated to a volume of 10 ml. Slow and careful layering of hexane (40 ml) on the top of the residual solution resulted in the formation of an inseparable compound mixture and a few colourless crystals suitable for X-ray single crystal diffraction analysis.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The hydrogen atom were positioned geometrically (C—H = 0.95 Å for aromatic, 0.98 Å for methyl H atoms) and refined as riding atoms with U_iso(H) = 1.5U_eq(C) for methyl or 1.2U_eq(C) for aromatic H atoms. A rotating group model was applied for methyl groups. Three reflections (100, 010, 001) were affected by the beam stop, and were therefore omitted from the refinement. Two non-coordinating toluene molecules disordered over inversion centres with occupancy factors of 0.5 were modelled by fitting the phenyl rings to regular hexagons, by constraining the C_ipso—C_Me bond distances to 1.52 (1) Å, and by using equal anisotropic displacement parameters for atoms C52, C53, C54, C55, C60, C62 and C65.

Table 3
Experimental details

Crystal data
Chemical formula	[Al₂La₂(CH₃)₆(C₂₀H₁₅O₂)₄(CH₃O)₂]·4C₇H₈
M_r	2001.86
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	13.8404 (6), 14.2089 (6), 14.6084 (7)
α, β, γ (°)	73.198 (1), 81.968 (1), 63.523 (1)
V (Å³)	2461.54 (19)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	0.93
Crystal size (mm)	0.43 × 0.17 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.713, 0.848
No. of measured, independent and observed [I > 2σ(I)] reflections	30779, 13082, 10174
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.111, 1.01
No. of reflections	13082
No. of parameters	596
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.25, −1.36
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008 ), SHELXL2017 (Sheldrick, 2015 ), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2015) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1877930

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989018015876/rz5247sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018015876/rz5247Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018015876/rz5247Isup3.cdx

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2015) and publCIF (Westrip, 2010).

Bis(µ₂-methanolato-κO:κO)hexamethylbis(µ₂-triphenylacetato-κO:κO')bis(µ₂-triphenylacetato-κ²O,O':κO)dialuminiumdilanthanum toluene tetrasolvate top

Crystal data top

[Al₂La₂(CH₃)₆(C₂₀H₁₅O₂)₄(CH₃O)₂]·4C₇H₈	Z = 1
M_r = 2001.86	F(000) = 1032
Triclinic, P1	D_x = 1.350 Mg m⁻³
a = 13.8404 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.2089 (6) Å	Cell parameters from 4587 reflections
c = 14.6084 (7) Å	θ = 2.5–27.3°
α = 73.198 (1)°	µ = 0.93 mm⁻¹
β = 81.968 (1)°	T = 100 K
γ = 63.523 (1)°	Block, colorless
V = 2461.54 (19) Å³	0.43 × 0.17 × 0.14 mm

Data collection top

Bruker APEXII CCD diffractometer	13082 independent reflections
Radiation source: fine-focus sealed tube	10174 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ω scans	θ_max = 29.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −18→18
T_min = 0.713, T_max = 0.848	k = −19→19
30779 measured reflections	l = −19→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0491P)²] where P = (F_o² + 2F_c²)/3
13082 reflections	(Δ/σ)_max = 0.001
596 parameters	Δρ_max = 1.25 e Å⁻³
2 restraints	Δρ_min = −1.36 e Å⁻³

Special details top

Experimental. moisture and air sensitive

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 > 2sigma(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	Occ. (<1)
La1	−0.03227 (2)	0.49487 (2)	0.37122 (2)	0.01306 (6)
Al1	−0.12529 (11)	0.40803 (10)	0.21948 (9)	0.0286 (3)
O1	−0.0005 (2)	0.3834 (3)	0.2697 (2)	0.0386 (7)
C1	0.0953 (4)	0.3005 (4)	0.2479 (4)	0.0524 (14)
H1A	0.088611	0.290505	0.185791	0.079*
H1B	0.109110	0.232657	0.297403	0.079*
H1C	0.155252	0.320192	0.245107	0.079*
C2	−0.2300 (4)	0.5359 (3)	0.2694 (3)	0.0336 (10)
H2A	−0.300473	0.565883	0.239855	0.050*
H2B	−0.203033	0.591960	0.253632	0.050*
H2C	−0.237368	0.512220	0.338947	0.050*
C3	−0.1116 (4)	0.4476 (4)	0.0776 (3)	0.0460 (12)
H3A	−0.097311	0.384953	0.053500	0.069*
H3B	−0.051864	0.468840	0.059015	0.069*
H3C	−0.178880	0.508554	0.050371	0.069*
C4	−0.1619 (4)	0.2840 (4)	0.2695 (3)	0.0406 (11)
H4A	−0.110910	0.223099	0.243557	0.061*
H4B	−0.235322	0.304856	0.250611	0.061*
H4C	−0.157613	0.261936	0.339463	0.061*
O2	−0.1140 (2)	0.3706 (2)	0.46652 (19)	0.0320 (7)
O3	−0.0402 (2)	0.4255 (2)	0.54830 (18)	0.0232 (6)
C5	−0.0957 (3)	0.3754 (3)	0.5459 (3)	0.0214 (8)
C6	−0.1398 (3)	0.3264 (3)	0.6418 (3)	0.0220 (8)
C7	−0.0810 (3)	0.3348 (3)	0.7189 (3)	0.0234 (8)
C8	0.0289 (3)	0.2683 (3)	0.7329 (3)	0.0271 (8)
H8	0.064082	0.213330	0.699308	0.033*
C9	0.0885 (4)	0.2798 (3)	0.7944 (3)	0.0307 (9)
H9	0.163386	0.233326	0.802589	0.037*
C10	0.0381 (4)	0.3596 (4)	0.8438 (3)	0.0340 (10)
H10	0.077959	0.367317	0.886831	0.041*
C11	−0.0703 (4)	0.4277 (4)	0.8303 (3)	0.0325 (10)
H11	−0.104716	0.482567	0.864064	0.039*
C12	−0.1300 (3)	0.4167 (3)	0.7672 (3)	0.0279 (9)
H12	−0.204174	0.465268	0.757361	0.033*
C13	−0.2633 (3)	0.3918 (3)	0.6482 (3)	0.0233 (8)
C14	−0.3158 (3)	0.3660 (4)	0.7337 (3)	0.0342 (10)
H14	−0.275619	0.309338	0.785860	0.041*
C15	−0.4279 (4)	0.4235 (4)	0.7427 (3)	0.0391 (11)
H15	−0.463027	0.406832	0.801646	0.047*
C16	−0.4875 (4)	0.5041 (4)	0.6668 (4)	0.0387 (11)
H16	−0.563524	0.542101	0.673235	0.046*
C17	−0.4364 (3)	0.5292 (3)	0.5818 (3)	0.0340 (10)
H17	−0.477381	0.584819	0.529442	0.041*
C18	−0.3253 (3)	0.4737 (3)	0.5721 (3)	0.0284 (9)
H18	−0.291035	0.491608	0.513002	0.034*
C19	−0.1186 (3)	0.2076 (3)	0.6507 (3)	0.0249 (8)
C20	−0.0899 (4)	0.1297 (3)	0.7379 (3)	0.0328 (10)
H20	−0.078929	0.148647	0.791600	0.039*
C21	−0.0772 (4)	0.0247 (4)	0.7475 (4)	0.0424 (11)
H21	−0.059311	−0.026807	0.807948	0.051*
C22	−0.0904 (4)	−0.0056 (4)	0.6695 (4)	0.0415 (12)
H22	−0.078727	−0.078289	0.675550	0.050*
C23	−0.1208 (3)	0.0713 (3)	0.5833 (3)	0.0340 (10)
H23	−0.131851	0.051784	0.530019	0.041*
C24	−0.1355 (3)	0.1779 (3)	0.5732 (3)	0.0276 (9)
H24	−0.157055	0.230159	0.513513	0.033*
O4	−0.1812 (2)	0.6313 (2)	0.43281 (18)	0.0240 (6)
O5	−0.1427 (2)	0.6352 (2)	0.57488 (19)	0.0263 (6)
C25	−0.2039 (3)	0.6717 (3)	0.5035 (3)	0.0227 (8)
C26	−0.3096 (3)	0.7777 (3)	0.5032 (3)	0.0227 (8)
C27	−0.2810 (3)	0.8697 (3)	0.4371 (3)	0.0231 (8)
C28	−0.1853 (3)	0.8743 (3)	0.4508 (3)	0.0301 (9)
H28	−0.137299	0.820458	0.499793	0.036*
C29	−0.1600 (3)	0.9568 (3)	0.3933 (3)	0.0337 (10)
H29	−0.093985	0.957802	0.402696	0.040*
C30	−0.2283 (4)	1.0370 (4)	0.3232 (3)	0.0368 (10)
H30	−0.210354	1.093329	0.284112	0.044*
C31	−0.3234 (4)	1.0339 (4)	0.3106 (3)	0.0382 (11)
H31	−0.371889	1.089322	0.262629	0.046*
C32	−0.3499 (3)	0.9516 (3)	0.3667 (3)	0.0304 (9)
H32	−0.416150	0.951342	0.356674	0.037*
C33	−0.3352 (3)	0.7907 (3)	0.6049 (3)	0.0257 (8)
C34	−0.3485 (3)	0.8825 (3)	0.6307 (3)	0.0314 (9)
H34	−0.339816	0.940681	0.584050	0.038*
C35	−0.3746 (4)	0.8894 (4)	0.7256 (4)	0.0437 (12)
H35	−0.383374	0.952358	0.742752	0.052*
C36	−0.3876 (4)	0.8057 (4)	0.7943 (3)	0.0447 (12)
H36	−0.404321	0.810532	0.858570	0.054*
C37	−0.3762 (3)	0.7144 (4)	0.7688 (3)	0.0382 (11)
H37	−0.386189	0.656965	0.815430	0.046*
C38	−0.3502 (3)	0.7074 (4)	0.6750 (3)	0.0311 (9)
H38	−0.342435	0.644566	0.658109	0.037*
C39	−0.4077 (3)	0.7783 (3)	0.4627 (3)	0.0229 (8)
C40	−0.4009 (3)	0.7506 (3)	0.3772 (3)	0.0257 (8)
H40	−0.334014	0.729044	0.343230	0.031*
C41	−0.4902 (3)	0.7541 (3)	0.3408 (3)	0.0300 (9)
H41	−0.482883	0.732093	0.283689	0.036*
C42	−0.5896 (3)	0.7893 (3)	0.3865 (3)	0.0316 (9)
H42	−0.650696	0.792166	0.361079	0.038*
C43	−0.5981 (3)	0.8199 (4)	0.4696 (3)	0.0334 (10)
H43	−0.666067	0.844944	0.501464	0.040*
C44	−0.5089 (3)	0.8148 (3)	0.5072 (3)	0.0287 (9)
H44	−0.516858	0.836590	0.564489	0.034*
C45	0.3342 (4)	−0.0048 (5)	1.0374 (4)	0.0480 (13)
C46	0.3902 (4)	−0.0087 (5)	0.9511 (4)	0.0585 (15)
H46	0.427274	−0.076125	0.934371	0.070*
C47	0.3928 (5)	0.0844 (6)	0.8891 (5)	0.074 (2)
H47	0.430937	0.080655	0.829926	0.088*
C48	0.3409 (6)	0.1817 (6)	0.9125 (5)	0.075 (2)
H48	0.344572	0.245235	0.870865	0.090*
C49	0.2825 (5)	0.1870 (5)	0.9978 (5)	0.0677 (19)
H49	0.244438	0.254804	1.013625	0.081*
C50	0.2794 (4)	0.0939 (5)	1.0599 (4)	0.0563 (15)
H50	0.239503	0.098150	1.118164	0.068*
C51	0.3334 (5)	−0.1067 (5)	1.1063 (4)	0.0719 (19)
H51A	0.398951	−0.169935	1.096588	0.108*
H51B	0.269827	−0.115018	1.094882	0.108*
H51C	0.330958	−0.101436	1.172030	0.108*
C52	1.0278 (10)	−0.0489 (11)	−0.0048 (11)	0.153 (5)	0.5
C53	1.0634 (11)	0.0326 (16)	−0.0286 (11)	0.153 (5)	0.5
H53	1.131932	0.020149	−0.058622	0.184*	0.5
C54	0.9986 (15)	0.1324 (13)	−0.0086 (9)	0.153 (5)	0.5
H54	1.022959	0.188084	−0.024851	0.184*	0.5
C55	0.8983 (14)	0.1506 (8)	0.0354 (9)	0.153 (5)	0.5
H55	0.854108	0.218810	0.049064	0.184*	0.5
C56	0.8628 (8)	0.0691 (11)	0.0592 (7)	0.088 (5)	0.5
H56	0.794229	0.081601	0.089209	0.106*	0.5
C57	0.9275 (10)	−0.0306 (9)	0.0391 (8)	0.066 (4)	0.5
H57	0.903200	−0.086335	0.055439	0.079*	0.5
C58	1.1043 (16)	−0.1507 (13)	−0.0328 (18)	0.167 (13)	0.5
H58A	1.147324	−0.132880	−0.088484	0.251*	0.5
H58B	1.063330	−0.184832	−0.048928	0.251*	0.5
H58C	1.152284	−0.201064	0.020591	0.251*	0.5
C59	0.4395 (9)	0.4875 (10)	−0.0082 (9)	0.088 (6)	0.5
C60	0.3781 (7)	0.5983 (10)	−0.0446 (7)	0.153 (5)	0.5
H60	0.308346	0.623626	−0.069200	0.184*	0.5
C61	0.4186 (10)	0.6720 (8)	−0.0449 (8)	0.079 (4)	0.5
H61	0.376605	0.747699	−0.069740	0.095*	0.5
C62	0.5206 (11)	0.6349 (10)	−0.0089 (8)	0.153 (5)	0.5
H62	0.548327	0.685295	−0.009072	0.184*	0.5
C63	0.5821 (8)	0.5242 (11)	0.0275 (8)	0.134 (11)	0.5
H63	0.651790	0.498818	0.052136	0.161*	0.5
C64	0.5415 (9)	0.4504 (8)	0.0278 (8)	0.104 (7)	0.5
H64	0.583532	0.374743	0.052676	0.125*	0.5
C65	0.421 (2)	0.4005 (15)	−0.0297 (12)	0.153 (5)	0.5
H65A	0.409788	0.418014	−0.098456	0.230*	0.5
H65B	0.357617	0.395283	0.005788	0.230*	0.5
H65C	0.484644	0.330811	−0.010675	0.230*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
La1	0.01304 (9)	0.01478 (10)	0.01329 (9)	−0.00636 (7)	−0.00039 (6)	−0.00557 (7)
Al1	0.0374 (7)	0.0314 (7)	0.0258 (6)	−0.0203 (6)	0.0014 (5)	−0.0117 (5)
O1	0.0376 (18)	0.049 (2)	0.0400 (18)	−0.0229 (16)	0.0015 (14)	−0.0198 (15)
C1	0.052 (3)	0.047 (3)	0.067 (4)	−0.018 (3)	−0.012 (3)	−0.025 (3)
C2	0.047 (3)	0.027 (2)	0.029 (2)	−0.018 (2)	0.0001 (19)	−0.0075 (18)
C3	0.060 (3)	0.065 (3)	0.030 (2)	−0.038 (3)	−0.004 (2)	−0.016 (2)
C4	0.047 (3)	0.041 (3)	0.047 (3)	−0.028 (2)	−0.005 (2)	−0.014 (2)
O2	0.0475 (18)	0.0466 (18)	0.0183 (14)	−0.0334 (16)	−0.0007 (13)	−0.0097 (13)
O3	0.0256 (14)	0.0203 (13)	0.0257 (14)	−0.0117 (11)	−0.0054 (11)	−0.0034 (11)
C5	0.0194 (18)	0.0199 (18)	0.025 (2)	−0.0081 (15)	0.0007 (15)	−0.0069 (15)
C6	0.0241 (19)	0.0241 (19)	0.0222 (19)	−0.0139 (16)	0.0003 (15)	−0.0067 (15)
C7	0.029 (2)	0.027 (2)	0.0189 (18)	−0.0185 (17)	−0.0003 (15)	−0.0031 (15)
C8	0.032 (2)	0.030 (2)	0.024 (2)	−0.0181 (18)	−0.0006 (16)	−0.0053 (16)
C9	0.037 (2)	0.034 (2)	0.027 (2)	−0.023 (2)	−0.0081 (18)	0.0000 (17)
C10	0.050 (3)	0.042 (3)	0.022 (2)	−0.032 (2)	−0.0093 (19)	−0.0013 (18)
C11	0.049 (3)	0.040 (3)	0.019 (2)	−0.027 (2)	0.0043 (18)	−0.0113 (18)
C12	0.036 (2)	0.031 (2)	0.023 (2)	−0.0203 (19)	0.0058 (17)	−0.0101 (17)
C13	0.026 (2)	0.027 (2)	0.025 (2)	−0.0165 (17)	0.0047 (16)	−0.0115 (16)
C14	0.031 (2)	0.033 (2)	0.035 (2)	−0.0144 (19)	0.0036 (19)	−0.0057 (19)
C15	0.036 (2)	0.043 (3)	0.041 (3)	−0.022 (2)	0.014 (2)	−0.012 (2)
C16	0.027 (2)	0.036 (3)	0.056 (3)	−0.014 (2)	0.003 (2)	−0.016 (2)
C17	0.031 (2)	0.029 (2)	0.044 (3)	−0.0140 (19)	−0.004 (2)	−0.0091 (19)
C18	0.029 (2)	0.032 (2)	0.027 (2)	−0.0155 (18)	0.0020 (17)	−0.0097 (17)
C19	0.0196 (19)	0.027 (2)	0.031 (2)	−0.0126 (16)	0.0006 (16)	−0.0089 (16)
C20	0.039 (2)	0.030 (2)	0.034 (2)	−0.021 (2)	−0.0053 (19)	−0.0018 (18)
C21	0.048 (3)	0.032 (3)	0.050 (3)	−0.024 (2)	−0.008 (2)	0.001 (2)
C22	0.035 (3)	0.024 (2)	0.067 (3)	−0.014 (2)	−0.005 (2)	−0.008 (2)
C23	0.025 (2)	0.030 (2)	0.055 (3)	−0.0130 (18)	0.000 (2)	−0.021 (2)
C24	0.022 (2)	0.026 (2)	0.038 (2)	−0.0117 (17)	−0.0013 (17)	−0.0103 (17)
O4	0.0219 (13)	0.0260 (14)	0.0255 (14)	−0.0085 (11)	−0.0015 (11)	−0.0110 (11)
O5	0.0196 (13)	0.0295 (15)	0.0269 (15)	−0.0044 (11)	−0.0029 (11)	−0.0120 (12)
C25	0.0205 (19)	0.0220 (19)	0.028 (2)	−0.0091 (15)	0.0005 (15)	−0.0101 (16)
C26	0.0171 (18)	0.0212 (19)	0.031 (2)	−0.0064 (15)	−0.0023 (15)	−0.0105 (16)
C27	0.0201 (18)	0.0227 (19)	0.030 (2)	−0.0083 (15)	−0.0005 (15)	−0.0125 (16)
C28	0.022 (2)	0.028 (2)	0.043 (3)	−0.0088 (17)	−0.0016 (18)	−0.0158 (19)
C29	0.024 (2)	0.034 (2)	0.053 (3)	−0.0145 (19)	0.0061 (19)	−0.024 (2)
C30	0.040 (3)	0.031 (2)	0.047 (3)	−0.022 (2)	0.010 (2)	−0.015 (2)
C31	0.040 (3)	0.030 (2)	0.046 (3)	−0.017 (2)	−0.007 (2)	−0.004 (2)
C32	0.028 (2)	0.027 (2)	0.039 (2)	−0.0135 (18)	−0.0037 (18)	−0.0078 (18)
C33	0.0177 (18)	0.033 (2)	0.026 (2)	−0.0042 (16)	−0.0031 (15)	−0.0161 (17)
C34	0.022 (2)	0.033 (2)	0.038 (2)	−0.0033 (17)	−0.0048 (17)	−0.0196 (19)
C35	0.035 (3)	0.046 (3)	0.046 (3)	−0.003 (2)	−0.007 (2)	−0.028 (2)
C36	0.035 (3)	0.065 (3)	0.031 (3)	−0.010 (2)	0.002 (2)	−0.027 (2)
C37	0.032 (2)	0.050 (3)	0.026 (2)	−0.011 (2)	−0.0008 (18)	−0.011 (2)
C38	0.027 (2)	0.038 (2)	0.027 (2)	−0.0113 (19)	0.0001 (17)	−0.0112 (18)
C39	0.0200 (18)	0.0205 (19)	0.027 (2)	−0.0074 (15)	−0.0043 (15)	−0.0049 (15)
C40	0.0205 (19)	0.029 (2)	0.027 (2)	−0.0090 (16)	−0.0006 (16)	−0.0084 (17)
C41	0.028 (2)	0.033 (2)	0.030 (2)	−0.0114 (18)	−0.0058 (17)	−0.0111 (18)
C42	0.024 (2)	0.038 (2)	0.038 (2)	−0.0156 (19)	−0.0055 (18)	−0.0116 (19)
C43	0.019 (2)	0.038 (2)	0.044 (3)	−0.0092 (18)	0.0008 (18)	−0.017 (2)
C44	0.023 (2)	0.030 (2)	0.032 (2)	−0.0074 (17)	−0.0003 (17)	−0.0139 (18)
C45	0.035 (3)	0.063 (4)	0.046 (3)	−0.023 (3)	−0.008 (2)	−0.006 (3)
C46	0.043 (3)	0.071 (4)	0.052 (3)	−0.019 (3)	0.004 (3)	−0.012 (3)
C47	0.058 (4)	0.099 (6)	0.054 (4)	−0.043 (4)	−0.009 (3)	0.014 (4)
C48	0.081 (5)	0.069 (5)	0.081 (5)	−0.047 (4)	−0.048 (4)	0.019 (4)
C49	0.069 (4)	0.054 (4)	0.081 (5)	−0.015 (3)	−0.043 (4)	−0.018 (3)
C50	0.048 (3)	0.074 (4)	0.050 (3)	−0.021 (3)	−0.014 (3)	−0.022 (3)
C51	0.071 (4)	0.081 (5)	0.064 (4)	−0.046 (4)	−0.012 (3)	0.010 (3)
C52	0.237 (14)	0.187 (12)	0.044 (5)	−0.111 (12)	−0.030 (6)	0.006 (6)
C53	0.237 (14)	0.187 (12)	0.044 (5)	−0.111 (12)	−0.030 (6)	0.006 (6)
C54	0.237 (14)	0.187 (12)	0.044 (5)	−0.111 (12)	−0.030 (6)	0.006 (6)
C55	0.237 (14)	0.187 (12)	0.044 (5)	−0.111 (12)	−0.030 (6)	0.006 (6)
C56	0.077 (10)	0.133 (15)	0.049 (8)	−0.037 (11)	−0.010 (7)	−0.023 (10)
C57	0.085 (9)	0.077 (9)	0.061 (8)	−0.075 (8)	−0.048 (7)	0.034 (6)
C58	0.19 (2)	0.063 (12)	0.20 (2)	0.052 (12)	−0.125 (19)	−0.094 (15)
C59	0.090 (12)	0.167 (18)	0.083 (12)	−0.115 (14)	0.040 (9)	−0.058 (12)
C60	0.237 (14)	0.187 (12)	0.044 (5)	−0.111 (12)	−0.030 (6)	0.006 (6)
C61	0.072 (9)	0.066 (9)	0.099 (11)	−0.038 (8)	0.035 (8)	−0.023 (8)
C62	0.237 (14)	0.187 (12)	0.044 (5)	−0.111 (12)	−0.030 (6)	0.006 (6)
C63	0.112 (15)	0.29 (3)	0.127 (16)	−0.16 (2)	0.072 (12)	−0.15 (2)
C64	0.095 (13)	0.22 (3)	0.046 (9)	−0.107 (16)	0.015 (7)	−0.042 (12)
C65	0.237 (14)	0.187 (12)	0.044 (5)	−0.111 (12)	−0.030 (6)	0.006 (6)

Geometric parameters (Å, º) top

La1—O1	2.336 (3)	C27—C32	1.383 (5)
La1—O2	2.501 (3)	C27—C28	1.400 (5)
La1—O3	2.494 (3)	C28—C29	1.383 (6)
La1—O3ⁱ	2.403 (2)	C28—H28	0.9500
La1—O4	2.396 (3)	C29—C30	1.370 (6)
La1—O5ⁱ	2.367 (3)	C29—H29	0.9500
La1—C2	3.042 (4)	C30—C31	1.376 (6)
La1—C5	2.892 (4)	C30—H30	0.9500
La1—C7ⁱ	3.318 (4)	C31—C32	1.385 (6)
La1—C8ⁱ	3.287 (4)	C31—H31	0.9500
La1—C9ⁱ	3.246 (4)	C32—H32	0.9500
La1—C10ⁱ	3.212 (4)	C33—C34	1.388 (5)
La1—C11ⁱ	3.201 (4)	C33—C38	1.398 (6)
La1—C12ⁱ	3.239 (4)	C34—C35	1.403 (6)
Al1—O1	1.819 (3)	C34—H34	0.9500
Al1—C2	2.014 (4)	C35—C36	1.380 (7)
Al1—C3	1.990 (5)	C35—H35	0.9500
Al1—C4	1.961 (4)	C36—C37	1.387 (7)
La1—Al1	3.4481 (12)	C36—H36	0.9500
La1—La1ⁱ	4.0432 (4)	C37—C38	1.388 (6)
O1—C1	1.398 (6)	C37—H37	0.9500
C1—H1A	0.9800	C38—H38	0.9500
C1—H1B	0.9800	C39—C40	1.394 (5)
C1—H1C	0.9800	C39—C44	1.396 (5)
C2—H2A	0.9800	C40—C41	1.388 (5)
C2—H2B	0.9800	C40—H40	0.9500
C2—H2C	0.9800	C41—C42	1.382 (6)
C3—H3A	0.9800	C41—H41	0.9500
C3—H3B	0.9800	C42—C43	1.378 (6)
C3—H3C	0.9800	C42—H42	0.9500
C4—H4A	0.9800	C43—C44	1.385 (6)
C4—H4B	0.9800	C43—H43	0.9500
C4—H4C	0.9800	C44—H44	0.9500
O2—C5	1.247 (4)	C45—C50	1.378 (8)
O3—C5	1.269 (4)	C45—C46	1.387 (7)
C5—C6	1.548 (5)	C45—C51	1.509 (7)
C6—C7	1.538 (5)	C46—C47	1.383 (8)
C6—C13	1.544 (5)	C46—H46	0.9500
C6—C19	1.548 (5)	C47—C48	1.365 (9)
C7—C8	1.394 (5)	C47—H47	0.9500
C7—C12	1.397 (5)	C48—C49	1.389 (9)
C8—C9	1.389 (5)	C48—H48	0.9500
C8—H8	0.9500	C49—C50	1.385 (9)
C9—C10	1.385 (6)	C49—H49	0.9500
C9—H9	0.9500	C50—H50	0.9500
C10—C11	1.379 (6)	C51—H51A	0.9800
C10—H10	0.9500	C51—H51B	0.9800
C11—C12	1.403 (5)	C51—H51C	0.9800
C11—H11	0.9500	C52—C53	1.3900
C12—H12	0.9500	C52—C57	1.3900
C13—C14	1.394 (5)	C52—C58	1.496 (8)
C13—C18	1.397 (5)	C53—C54	1.3900
C14—C15	1.402 (6)	C53—H53	0.9500
C14—H14	0.9500	C54—C55	1.3900
C15—C16	1.378 (6)	C54—H54	0.9500
C15—H15	0.9500	C55—C56	1.3900
C16—C17	1.376 (6)	C55—H55	0.9500
C16—H16	0.9500	C56—C57	1.3900
C17—C18	1.389 (6)	C56—H56	0.9500
C17—H17	0.9500	C57—H57	0.9500
C18—H18	0.9500	C58—H58A	0.9800
C19—C20	1.393 (6)	C58—H58B	0.9800
C19—C24	1.397 (5)	C58—H58C	0.9800
C20—C21	1.388 (6)	C59—C60	1.3900
C20—H20	0.9500	C59—C64	1.3900
C21—C22	1.389 (7)	C59—C65	1.489 (9)
C21—H21	0.9500	C60—C61	1.3900
C22—C23	1.379 (6)	C60—H60	0.9500
C22—H22	0.9500	C61—C62	1.3900
C23—C24	1.400 (5)	C61—H61	0.9500
C23—H23	0.9500	C62—C63	1.3900
C24—H24	0.9500	C62—H62	0.9500
O4—C25	1.260 (4)	C63—C64	1.3900
O5—C25	1.271 (4)	C63—H63	0.9500
C25—C26	1.563 (5)	C64—H64	0.9500
C26—C33	1.522 (5)	C65—H65A	0.9800
C26—C39	1.550 (5)	C65—H65B	0.9800
C26—C27	1.557 (5)	C65—H65C	0.9800

O1—La1—O5ⁱ	82.41 (10)	C10—C9—H9	120.2
O1—La1—O4	139.15 (10)	C8—C9—H9	120.2
O5ⁱ—La1—O4	135.39 (9)	C11—C10—C9	119.8 (4)
O1—La1—O3ⁱ	147.59 (10)	C11—C10—H10	120.1
O5ⁱ—La1—O3ⁱ	71.61 (9)	C9—C10—H10	120.1
O4—La1—O3ⁱ	72.32 (9)	C10—C11—C12	120.6 (4)
O1—La1—O3	121.24 (10)	C10—C11—H11	119.7
O5ⁱ—La1—O3	71.46 (9)	C12—C11—H11	119.7
O4—La1—O3	71.58 (9)	C7—C12—C11	120.3 (4)
O3ⁱ—La1—O3	68.70 (10)	C7—C12—H12	119.8
O1—La1—O2	78.88 (10)	C11—C12—H12	119.8
O5ⁱ—La1—O2	91.47 (10)	C14—C13—C18	118.4 (4)
O4—La1—O2	84.39 (9)	C14—C13—C6	118.1 (4)
O3ⁱ—La1—O2	119.83 (8)	C18—C13—C6	123.5 (3)
O3—La1—O2	51.29 (8)	C13—C14—C15	120.0 (4)
O1—La1—C5	101.05 (11)	C13—C14—H14	120.0
O5ⁱ—La1—C5	82.20 (10)	C15—C14—H14	120.0
O4—La1—C5	75.29 (10)	C16—C15—C14	120.6 (4)
O3ⁱ—La1—C5	94.40 (9)	C16—C15—H15	119.7
O3—La1—C5	25.94 (9)	C14—C15—H15	119.7
O2—La1—C5	25.44 (9)	C17—C16—C15	119.7 (4)
O1—La1—C2	64.73 (11)	C17—C16—H16	120.1
O5ⁱ—La1—C2	144.59 (10)	C15—C16—H16	120.1
O4—La1—C2	74.60 (10)	C16—C17—C18	120.3 (4)
O3ⁱ—La1—C2	143.78 (10)	C16—C17—H17	119.9
O3—La1—C2	113.77 (10)	C18—C17—H17	119.9
O2—La1—C2	70.40 (10)	C17—C18—C13	120.9 (4)
C5—La1—C2	91.12 (11)	C17—C18—H18	119.5
O1—La1—C11ⁱ	67.47 (11)	C13—C18—H18	119.5
O5ⁱ—La1—C11ⁱ	89.35 (11)	C20—C19—C24	118.4 (4)
O4—La1—C11ⁱ	117.69 (10)	C20—C19—C6	120.8 (3)
O3ⁱ—La1—C11ⁱ	92.66 (9)	C24—C19—C6	120.7 (4)
O3—La1—C11ⁱ	156.40 (10)	C21—C20—C19	120.9 (4)
O2—La1—C11ⁱ	145.92 (9)	C21—C20—H20	119.5
C5—La1—C11ⁱ	166.69 (10)	C19—C20—H20	119.5
C2—La1—C11ⁱ	89.83 (11)	C20—C21—C22	120.6 (4)
O1—La1—C10ⁱ	73.06 (11)	C20—C21—H21	119.7
O5ⁱ—La1—C10ⁱ	114.19 (11)	C22—C21—H21	119.7
O4—La1—C10ⁱ	97.09 (11)	C23—C22—C21	119.0 (4)
O3ⁱ—La1—C10ⁱ	99.91 (9)	C23—C22—H22	120.5
O3—La1—C10ⁱ	165.67 (10)	C21—C22—H22	120.5
O2—La1—C10ⁱ	138.28 (9)	C22—C23—C24	120.9 (4)
C5—La1—C10ⁱ	160.95 (11)	C22—C23—H23	119.6
C2—La1—C10ⁱ	69.92 (11)	C24—C23—H23	119.6
C11ⁱ—La1—C10ⁱ	24.84 (11)	C19—C24—C23	120.2 (4)
O1—La1—C12ⁱ	86.54 (10)	C19—C24—H24	119.9
O5ⁱ—La1—C12ⁱ	75.20 (10)	C23—C24—H24	119.9
O4—La1—C12ⁱ	114.12 (10)	C25—O4—La1	139.1 (2)
O3ⁱ—La1—C12ⁱ	68.61 (9)	C25—O5—La1ⁱ	141.2 (2)
O3—La1—C12ⁱ	132.01 (9)	O4—C25—O5	124.1 (3)
O2—La1—C12ⁱ	161.48 (10)	O4—C25—C26	119.6 (3)
C5—La1—C12ⁱ	155.02 (11)	O5—C25—C26	116.2 (3)
C2—La1—C12ⁱ	113.49 (11)	C33—C26—C39	109.6 (3)
C11ⁱ—La1—C12ⁱ	25.16 (10)	C33—C26—C27	111.5 (3)
C10ⁱ—La1—C12ⁱ	44.00 (11)	C39—C26—C27	109.9 (3)
O1—La1—C9ⁱ	96.80 (11)	C33—C26—C25	109.0 (3)
O5ⁱ—La1—C9ⁱ	125.80 (10)	C39—C26—C25	113.0 (3)
O4—La1—C9ⁱ	74.39 (10)	C27—C26—C25	103.8 (3)
O3ⁱ—La1—C9ⁱ	83.65 (9)	C32—C27—C28	117.8 (4)
O3—La1—C9ⁱ	141.16 (9)	C32—C27—C26	122.1 (3)
O2—La1—C9ⁱ	141.89 (10)	C28—C27—C26	120.0 (3)
C5—La1—C9ⁱ	148.71 (11)	C29—C28—C27	120.4 (4)
C2—La1—C9ⁱ	73.57 (10)	C29—C28—H28	119.8
C11ⁱ—La1—C9ⁱ	43.54 (11)	C27—C28—H28	119.8
C10ⁱ—La1—C9ⁱ	24.77 (11)	C30—C29—C28	121.3 (4)
C12ⁱ—La1—C9ⁱ	50.79 (11)	C30—C29—H29	119.3
O1—La1—C8ⁱ	115.26 (11)	C28—C29—H29	119.3
O5ⁱ—La1—C8ⁱ	109.86 (10)	C29—C30—C31	118.4 (4)
O4—La1—C8ⁱ	71.71 (10)	C29—C30—H30	120.8
O3ⁱ—La1—C8ⁱ	59.29 (9)	C31—C30—H30	120.8
O3—La1—C8ⁱ	122.88 (9)	C30—C31—C32	121.2 (4)
O2—La1—C8ⁱ	155.27 (10)	C30—C31—H31	119.4
C5—La1—C8ⁱ	142.66 (10)	C32—C31—H31	119.4
C2—La1—C8ⁱ	96.47 (10)	C27—C32—C31	120.8 (4)
C11ⁱ—La1—C8ⁱ	50.24 (11)	C27—C32—H32	119.6
C10ⁱ—La1—C8ⁱ	43.27 (10)	C31—C32—H32	119.6
C12ⁱ—La1—C8ⁱ	42.94 (10)	C34—C33—C38	118.4 (4)
C9ⁱ—La1—C8ⁱ	24.55 (9)	C34—C33—C26	123.6 (4)
O1—La1—C7ⁱ	110.09 (10)	C38—C33—C26	118.0 (3)
O5ⁱ—La1—C7ⁱ	85.71 (10)	C33—C34—C35	120.1 (4)
O4—La1—C7ⁱ	90.93 (9)	C33—C34—H34	119.9
O3ⁱ—La1—C7ⁱ	50.27 (9)	C35—C34—H34	119.9
O3—La1—C7ⁱ	118.89 (8)	C36—C35—C34	120.7 (4)
O2—La1—C7ⁱ	170.08 (9)	C36—C35—H35	119.6
C5—La1—C7ⁱ	144.67 (10)	C34—C35—H35	119.6
C2—La1—C7ⁱ	116.78 (10)	C35—C36—C37	119.5 (4)
C11ⁱ—La1—C7ⁱ	43.70 (10)	C35—C36—H36	120.2
C10ⁱ—La1—C7ⁱ	50.94 (10)	C37—C36—H36	120.2
C12ⁱ—La1—C7ⁱ	24.56 (9)	C36—C37—C38	119.8 (5)
C9ⁱ—La1—C7ⁱ	43.50 (10)	C36—C37—H37	120.1
C8ⁱ—La1—C7ⁱ	24.35 (9)	C38—C37—H37	120.1
O1—La1—Al1	29.38 (8)	C37—C38—C33	121.3 (4)
O5ⁱ—La1—Al1	110.37 (7)	C37—C38—H38	119.3
O4—La1—Al1	109.78 (6)	C33—C38—H38	119.3
O3ⁱ—La1—Al1	169.94 (6)	C40—C39—C44	117.2 (3)
O3—La1—Al1	121.36 (6)	C40—C39—C26	121.8 (3)
O2—La1—Al1	70.20 (6)	C44—C39—C26	120.8 (3)
C5—La1—Al1	95.64 (8)	C41—C40—C39	121.1 (4)
C2—La1—Al1	35.46 (8)	C41—C40—H40	119.5
C11ⁱ—La1—Al1	77.62 (7)	C39—C40—H40	119.5
C10ⁱ—La1—Al1	70.17 (7)	C42—C41—C40	120.9 (4)
C12ⁱ—La1—Al1	102.03 (7)	C42—C41—H41	119.6
C9ⁱ—La1—Al1	87.46 (7)	C40—C41—H41	119.6
C8ⁱ—La1—Al1	111.50 (7)	C43—C42—C41	118.6 (4)
C7ⁱ—La1—Al1	119.68 (7)	C43—C42—H42	120.7
O1—La1—La1ⁱ	145.25 (8)	C41—C42—H42	120.7
O5ⁱ—La1—La1ⁱ	67.44 (6)	C42—C43—C44	120.8 (4)
O4—La1—La1ⁱ	67.95 (6)	C42—C43—H43	119.6
O3ⁱ—La1—La1ⁱ	35.07 (6)	C44—C43—H43	119.6
O3—La1—La1ⁱ	33.63 (6)	C43—C44—C39	121.4 (4)
O2—La1—La1ⁱ	84.84 (6)	C43—C44—H44	119.3
C5—La1—La1ⁱ	59.40 (7)	C39—C44—H44	119.3
C2—La1—La1ⁱ	136.72 (8)	C50—C45—C46	118.9 (6)
C11ⁱ—La1—La1ⁱ	126.35 (7)	C50—C45—C51	120.2 (6)
C10ⁱ—La1—La1ⁱ	134.41 (7)	C46—C45—C51	120.9 (6)
C12ⁱ—La1—La1ⁱ	101.30 (7)	C47—C46—C45	120.8 (6)
C9ⁱ—La1—La1ⁱ	114.49 (7)	C47—C46—H46	119.6
C8ⁱ—La1—La1ⁱ	91.79 (7)	C45—C46—H46	119.6
C7ⁱ—La1—La1ⁱ	85.30 (6)	C48—C47—C46	120.3 (7)
Al1—La1—La1ⁱ	154.99 (2)	C48—C47—H47	119.8
O1—Al1—C4	111.77 (18)	C46—C47—H47	119.8
O1—Al1—C3	108.32 (18)	C47—C48—C49	119.4 (6)
C4—Al1—C3	113.2 (2)	C47—C48—H48	120.3
O1—Al1—C2	100.03 (17)	C49—C48—H48	120.3
C4—Al1—C2	110.7 (2)	C50—C49—C48	120.4 (6)
C3—Al1—C2	112.0 (2)	C50—C49—H49	119.8
O1—Al1—La1	39.05 (10)	C48—C49—H49	119.8
C4—Al1—La1	120.09 (15)	C45—C50—C49	120.2 (6)
C3—Al1—La1	124.87 (14)	C45—C50—H50	119.9
C2—Al1—La1	61.19 (13)	C49—C50—H50	119.9
C1—O1—Al1	118.0 (3)	C45—C51—H51A	109.5
C1—O1—La1	130.3 (3)	C45—C51—H51B	109.5
Al1—O1—La1	111.57 (15)	H51A—C51—H51B	109.5
O1—C1—H1A	109.5	C45—C51—H51C	109.5
O1—C1—H1B	109.5	H51A—C51—H51C	109.5
H1A—C1—H1B	109.5	H51B—C51—H51C	109.5
O1—C1—H1C	109.5	C53—C52—C57	120.0
H1A—C1—H1C	109.5	C53—C52—C58	114.2 (15)
H1B—C1—H1C	109.5	C57—C52—C58	125.7 (15)
Al1—C2—La1	83.34 (15)	C54—C53—C52	120.0
Al1—C2—H2A	109.5	C54—C53—H53	120.0
La1—C2—H2A	166.5	C52—C53—H53	120.0
Al1—C2—H2B	109.5	C55—C54—C53	120.0
La1—C2—H2B	60.7	C55—C54—H54	120.0
H2A—C2—H2B	109.5	C53—C54—H54	120.0
Al1—C2—H2C	109.5	C54—C55—C56	120.0
La1—C2—H2C	68.5	C54—C55—H55	120.0
H2A—C2—H2C	109.5	C56—C55—H55	120.0
H2B—C2—H2C	109.5	C55—C56—C57	120.0
Al1—C3—H3A	109.5	C55—C56—H56	120.0
Al1—C3—H3B	109.5	C57—C56—H56	120.0
H3A—C3—H3B	109.5	C56—C57—C52	120.0
Al1—C3—H3C	109.5	C56—C57—H57	120.0
H3A—C3—H3C	109.5	C52—C57—H57	120.0
H3B—C3—H3C	109.5	C52—C58—H58A	109.5
Al1—C4—H4A	109.5	C52—C58—H58B	109.5
Al1—C4—H4B	109.5	H58A—C58—H58B	109.5
H4A—C4—H4B	109.5	C52—C58—H58C	109.5
Al1—C4—H4C	109.5	H58A—C58—H58C	109.5
H4A—C4—H4C	109.5	H58B—C58—H58C	109.5
H4B—C4—H4C	109.5	C60—C59—C64	120.0
C5—O2—La1	95.0 (2)	C60—C59—C65	124.4 (10)
C5—O3—La1ⁱ	152.7 (2)	C64—C59—C65	113.0 (12)
C5—O3—La1	94.8 (2)	C61—C60—C59	120.0
La1ⁱ—O3—La1	111.30 (9)	C61—C60—H60	120.0
O2—C5—O3	118.4 (3)	C59—C60—H60	120.0
O2—C5—C6	123.7 (3)	C60—C61—C62	120.0
O3—C5—C6	117.8 (3)	C60—C61—H61	120.0
O2—C5—La1	59.51 (19)	C62—C61—H61	120.0
O3—C5—La1	59.24 (19)	C63—C62—C61	120.0
C6—C5—La1	172.3 (2)	C63—C62—H62	120.0
C7—C6—C13	111.8 (3)	C61—C62—H62	120.0
C7—C6—C5	104.6 (3)	C62—C63—C64	120.0
C13—C6—C5	110.0 (3)	C62—C63—H63	120.0
C7—C6—C19	112.2 (3)	C64—C63—H63	120.0
C13—C6—C19	106.7 (3)	C63—C64—C59	120.0
C5—C6—C19	111.6 (3)	C63—C64—H64	120.0
C8—C7—C12	117.8 (4)	C59—C64—H64	120.0
C8—C7—C6	119.4 (3)	C59—C65—H65A	109.5
C12—C7—C6	122.2 (4)	C59—C65—H65B	109.5
C9—C8—C7	122.0 (4)	H65A—C65—H65B	109.5
C9—C8—H8	119.0	C59—C65—H65C	109.5
C7—C8—H8	119.0	H65A—C65—H65C	109.5
C10—C9—C8	119.5 (4)	H65B—C65—H65C	109.5

C4—Al1—O1—C1	65.1 (4)	O5—C25—C26—C39	−142.5 (3)
C3—Al1—O1—C1	−60.3 (4)	O4—C25—C26—C27	−77.6 (4)
C2—Al1—O1—C1	−177.7 (4)	O5—C25—C26—C27	98.5 (4)
La1—Al1—O1—C1	176.5 (4)	C33—C26—C27—C32	−108.6 (4)
C4—Al1—O1—La1	−111.4 (2)	C39—C26—C27—C32	13.0 (5)
C3—Al1—O1—La1	123.2 (2)	C25—C26—C27—C32	134.2 (4)
C2—Al1—O1—La1	5.8 (2)	C33—C26—C27—C28	68.4 (4)
La1—O2—C5—O3	−6.3 (4)	C39—C26—C27—C28	−170.0 (3)
La1—O2—C5—C6	171.8 (3)	C25—C26—C27—C28	−48.8 (4)
La1ⁱ—O3—C5—O2	169.6 (3)	C32—C27—C28—C29	−1.8 (6)
La1—O3—C5—O2	6.4 (4)	C26—C27—C28—C29	−179.0 (4)
La1ⁱ—O3—C5—C6	−8.6 (7)	C27—C28—C29—C30	1.3 (6)
La1—O3—C5—C6	−171.9 (3)	C28—C29—C30—C31	−0.1 (7)
La1ⁱ—O3—C5—La1	163.3 (5)	C29—C30—C31—C32	−0.5 (7)
O2—C5—C6—C7	170.6 (4)	C28—C27—C32—C31	1.2 (6)
O3—C5—C6—C7	−11.2 (4)	C26—C27—C32—C31	178.3 (4)
O2—C5—C6—C13	−69.2 (5)	C30—C31—C32—C27	−0.1 (7)
O3—C5—C6—C13	109.0 (4)	C39—C26—C33—C34	−112.0 (4)
O2—C5—C6—C19	49.1 (5)	C27—C26—C33—C34	9.8 (5)
O3—C5—C6—C19	−132.8 (3)	C25—C26—C33—C34	123.8 (4)
C13—C6—C7—C8	170.5 (3)	C39—C26—C33—C38	65.4 (4)
C5—C6—C7—C8	−70.4 (4)	C27—C26—C33—C38	−172.8 (3)
C19—C6—C7—C8	50.7 (5)	C25—C26—C33—C38	−58.7 (4)
C13—C6—C7—C12	−18.2 (5)	C38—C33—C34—C35	1.0 (6)
C5—C6—C7—C12	100.9 (4)	C26—C33—C34—C35	178.4 (4)
C19—C6—C7—C12	−138.0 (4)	C33—C34—C35—C36	−0.1 (7)
C12—C7—C8—C9	1.7 (6)	C34—C35—C36—C37	−0.9 (7)
C6—C7—C8—C9	173.3 (3)	C35—C36—C37—C38	1.0 (7)
C7—C8—C9—C10	0.0 (6)	C36—C37—C38—C33	−0.1 (6)
C8—C9—C10—C11	−1.0 (6)	C34—C33—C38—C37	−0.9 (6)
C9—C10—C11—C12	0.2 (6)	C26—C33—C38—C37	−178.5 (4)
C8—C7—C12—C11	−2.4 (6)	C33—C26—C39—C40	−169.7 (4)
C6—C7—C12—C11	−173.8 (3)	C27—C26—C39—C40	67.6 (4)
C10—C11—C12—C7	1.5 (6)	C25—C26—C39—C40	−47.9 (5)
C7—C6—C13—C14	−58.2 (4)	C33—C26—C39—C44	15.3 (5)
C5—C6—C13—C14	−173.9 (3)	C27—C26—C39—C44	−107.4 (4)
C19—C6—C13—C14	64.8 (4)	C25—C26—C39—C44	137.1 (4)
C7—C6—C13—C18	123.4 (4)	C44—C39—C40—C41	−3.2 (6)
C5—C6—C13—C18	7.6 (5)	C26—C39—C40—C41	−178.4 (4)
C19—C6—C13—C18	−113.7 (4)	C39—C40—C41—C42	2.6 (6)
C18—C13—C14—C15	−1.6 (6)	C40—C41—C42—C43	−0.6 (6)
C6—C13—C14—C15	179.8 (4)	C41—C42—C43—C44	−0.6 (7)
C13—C14—C15—C16	1.6 (7)	C42—C43—C44—C39	−0.2 (7)
C14—C15—C16—C17	−0.8 (7)	C40—C39—C44—C43	2.1 (6)
C15—C16—C17—C18	0.1 (7)	C26—C39—C44—C43	177.3 (4)
C16—C17—C18—C13	−0.2 (6)	C50—C45—C46—C47	1.0 (8)
C14—C13—C18—C17	1.0 (6)	C51—C45—C46—C47	−178.5 (5)
C6—C13—C18—C17	179.4 (3)	C45—C46—C47—C48	0.6 (9)
C7—C6—C19—C20	24.5 (5)	C46—C47—C48—C49	−2.0 (9)
C13—C6—C19—C20	−98.2 (4)	C47—C48—C49—C50	1.8 (9)
C5—C6—C19—C20	141.6 (4)	C46—C45—C50—C49	−1.2 (8)
C7—C6—C19—C24	−160.1 (3)	C51—C45—C50—C49	178.3 (5)
C13—C6—C19—C24	77.2 (4)	C48—C49—C50—C45	−0.2 (8)
C5—C6—C19—C24	−43.1 (5)	C57—C52—C53—C54	0.0
C24—C19—C20—C21	0.7 (6)	C58—C52—C53—C54	178.4 (16)
C6—C19—C20—C21	176.1 (4)	C52—C53—C54—C55	0.0
C19—C20—C21—C22	1.5 (7)	C53—C54—C55—C56	0.0
C20—C21—C22—C23	−2.7 (7)	C54—C55—C56—C57	0.0
C21—C22—C23—C24	1.6 (7)	C55—C56—C57—C52	0.0
C20—C19—C24—C23	−1.7 (6)	C53—C52—C57—C56	0.0
C6—C19—C24—C23	−177.2 (3)	C58—C52—C57—C56	−178.3 (18)
C22—C23—C24—C19	0.5 (6)	C64—C59—C60—C61	0.0
La1—O4—C25—O5	−7.1 (6)	C65—C59—C60—C61	−160.7 (16)
La1—O4—C25—C26	168.7 (2)	C59—C60—C61—C62	0.0
La1ⁱ—O5—C25—O4	6.7 (7)	C60—C61—C62—C63	0.0
La1ⁱ—O5—C25—C26	−169.3 (3)	C61—C62—C63—C64	0.0
O4—C25—C26—C33	163.5 (3)	C62—C63—C64—C59	0.0
O5—C25—C26—C33	−20.4 (5)	C60—C59—C64—C63	0.0
O4—C25—C26—C39	41.4 (5)	C65—C59—C64—C63	162.8 (13)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C33–C38, C39–C44, C52–C57 and C19–C24 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C······Cg1ⁱ	0.98	2.69	3.425 (6)	132
C17—H17······Cg2	0.95	2.71	3.485 (4)	139
C21—H21······Cg3ⁱⁱ	0.95	2.93	3.677 (8)	136
C29—H29······Cg4	0.95	2.62	3.415 (4)	142
C32—H32······Cg2	0.95	2.95	3.654 (5)	132
C44—H44······Cg1	0.95	2.88	3.592 (5)	132

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1.

Funding information

Funding for this research was provided by: the Russian Science Foundation (grant No. 17-13-01357) and the TIPS RAS State Plan.

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