Bis[N,N′-bis­(2,6-diisopropyl­phen­yl)ethane-1,2-diimine]-1κ2N,N′;2κ2N,N′-tri-μ-trichlorido-1:2κ6Cl:Cl-chlorido-1κCl-tetra­hydro­furan-2κO-dichromium(II) dichloro­methane 4.5-solvate

Peitz, S.; Peulecke, N.; Müller, B.H.; Spannenberg, A.; Rosenthal, U.

doi:10.1107/S1600536809047266

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1574

doi:10.1107/S1600536809047266

Open

access

Bis[N,N′-bis(2,6-diisopropylphenyl)ethane-1,2-diimine]-1κ²N,N′;2κ²N,N′-tri-μ-trichlorido-1:2κ⁶Cl:Cl-chlorido-1κCl-tetrahydrofuran-2κO-dichromium(II) dichloromethane 4.5-solvate

Stephan Peitz,^a ^* Normen Peulecke,^a Bernd H. Müller,^a Anke Spannenberg ^a and Uwe Rosenthal ^a

^aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
^*Correspondence e-mail: stephan.peitz@catalysis.de

(Received 21 October 2009; accepted 9 November 2009; online 14 November 2009)

In the molecular structure of the title compound, [Cr₂Cl₄(C₂₆H₃₆N₂)₂(C₄H₈O)]·4.5CH₂Cl₂, the two Cr^II centers are bridged by three Cl atoms, forming a dinuclear complex. Each Cr^II center is coordinated by one chelating bis(2,6-diisopropylphenyl)ethane-1,2-diimine ligand via both N atoms. An additional chloride ion binds to one chromium center, whereas an additional tetrahydrofuran molecule coordinates to the second Cr^II center. The coordination geometry at each Cr^II center can be best described as distorted octahedral.

Related literature

For a different crystal structure of the title compound from diethylether, see: Kreisel et al. (2008 ). For binuclear chromium complexes, see: Dietel et al. (2006 ); Kreisel et al. (2007 ); Wagner et al. (2009 ). For a different product of the reaction described here, obtained by crystallization of the raw material from acetonitrile, see: Peitz et al. (2009 ).

Experimental

Crystal data

[Cr₂Cl₄(C₂₆H₃₆N₂)₂(C₄H₈O)]·4.5CH₂Cl₂
M_r = 1453.21
Monoclinic, P 2₁ /c
a = 18.2545 (6) Å
b = 15.4111 (4) Å
c = 27.3121 (7) Å
β = 105.160 (2)°
V = 7416.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 200 K
0.50 × 0.50 × 0.37 mm

Data collection

STOE IPDS II diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ) T_min = 0.672, T_max = 0.810
94968 measured reflections
13785 independent reflections
9450 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.123
S = 0.93
13785 reflections
747 parameters
20 restraints
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047266/im2155sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047266/im2155Isup2.hkl

checkCIF report

Comment top

Binuclear chromium complexes have been investigated concerning their structural and electronic features (Dietel et al., 2006). Additionally, chromium-chromium interactions are of great interest due to the features of metal-metal multiple bonds. (Wagner et al., 2009). With the same ligand used here, a binuclear chromium complex with the shortest metal-metal bond at that time was isolated (Kreisel et al., 2007).

We became interested in chromium complexes with this type of ligand during our studies on binuclear chromium complexes. Therefore, we wanted to examine the N,N'-chelating diimine ligand in combination with chromium in order to find differences and similarities in coordination chemistry compared to other ligands forming binuclear complexes. We deployed a simple preparation procedure that is described here, to obtain the complex for structural investigations. Depending on the solvent used for crystallization of the raw material, mono- or binuclear complexes can be formed out of the educts (Peitz et al., 2009).

The molecular structure of the title compound shows two chromium(II) centers that are bridged by three chlorine atoms to form a binuclear complex (Fig. 1). Each chromium is coordinated by one chelating diimine ligand, (i-Pr)₂C₆H₃–NC(H)–C(H)N–C₆H₃(i-Pr)₂, via both N atoms of each ligand. An additional chloride ion binds to one chromium center, whereas an additional THF molecule coordinates to the second chromium center. The coordination geometry at each chromium center can be best described as distorted octahedral. Cr1 deviates from the N1,C1,C2,N2 plane by 0.45 Å, Cr2 from the N3,C27,C28,N4 plane by 0.28 Å. The NCCN backbones of the ligands are twisted in an angle of 62.1 (1)° against each other. The asymmetric unit additionally contains 4.5 solvent molecules dichloromethane per dinuclear complex unit. The title compound was previously investigated by X-ray analysis but single crystals were obtained from a different solvent and besides two molecules [(C₂₆H₃₆N₂)CrCl(µ-Cl)₃Cr(THF)(C₂₆H₃₆N₂)] they contained disordered diethyl ether molecules (space group P2₁/n; a = 15.3679 (15), b = 40.969 (4), c = 22.124 (2) Å, β = 108.121 (2)°).

Related literature top

For a different crystal structure of the title compound from diethylether, see: Kreisel et al. (2008). For binuclear chromium complexes, see: Dietel et al. (2006); Kreisel et al. (2007); Wagner et al. (2009). For a different product of the reaction described here, obtained by crystallization of the raw material from acetonitrile, see: Peitz et al. (2009).

Experimental top

CrCl₂(THF)₂ (1.50 g, 5.66 mmol) and N,N'-bis(2,6- diisopropylphenyl)ethane-1,2-diimine (2.13 g, 5.66 mmol) were dissolved in 20 ml of dichloromethane at room temperature and stirred over night. After removal of all volatiles in vacuum the residue was washed with small amounts of n-hexane to yield 3.05 g (93%) of green complex. Crystallization in dichloromethane/n-hexane (1:1) yielded dark-green single crystals suitable for X-ray analysis.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound showing the atom-labelling scheme. Thermal ellipsoids are drawn at the 30% probability level. Hydrogen atoms are omitted for clarity. For the disordered THF molecule atoms with higher occupancy are shown. The asymmetric unit additionally contains solvent molecules which are not depicted.

Bis[N,N'-bis(2,6-diisopropylphenyl)ethane-1,2-diimine]- 1κ²N,N';2κ²N,N'-tri-µ-trichlorido- 1:2κ⁶Cl:Cl- chlorido-1κCl-tetrahydrofuran-2κO-dichromium(II) dichloromethane 4.5-solvate top

Crystal data top

[Cr₂Cl₄(C₂₆H₃₆N₂)₂(C₄H₈O)]·4.5CH₂Cl₂	F(000) = 3028
M_r = 1453.21	D_x = 1.302 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13579 reflections
a = 18.2545 (6) Å	θ = 1.5–27.1°
b = 15.4111 (4) Å	µ = 0.80 mm⁻¹
c = 27.3121 (7) Å	T = 200 K
β = 105.160 (2)°	Prism, dark-green
V = 7416.1 (4) Å³	0.50 × 0.50 × 0.37 mm
Z = 4

Data collection top

STOE IPDS II diffractometer	13785 independent reflections
Radiation source: fine-focus sealed tube	9450 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scans	θ_max = 25.5°, θ_min = 1.5°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	h = −22→22
T_min = 0.672, T_max = 0.810	k = −18→18
94968 measured reflections	l = −33→31

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.078P)²] where P = (F_o² + 2F_c²)/3
13785 reflections	(Δ/σ)_max = 0.001
747 parameters	Δρ_max = 0.84 e Å⁻³
20 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

[Cr₂Cl₄(C₂₆H₃₆N₂)₂(C₄H₈O)]·4.5CH₂Cl₂	V = 7416.1 (4) Å³
M_r = 1453.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.2545 (6) Å	µ = 0.80 mm⁻¹
b = 15.4111 (4) Å	T = 200 K
c = 27.3121 (7) Å	0.50 × 0.50 × 0.37 mm
β = 105.160 (2)°

Data collection top

STOE IPDS II diffractometer	13785 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	9450 reflections with I > 2σ(I)
T_min = 0.672, T_max = 0.810	R_int = 0.053
94968 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	20 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 0.93	Δρ_max = 0.84 e Å⁻³
13785 reflections	Δρ_min = −0.57 e Å⁻³
747 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	Occ. (<1)
C1	0.11225 (16)	0.80860 (18)	0.29570 (11)	0.0283 (6)
H1A	0.0823	0.8593	0.2863	0.034*
C2	0.10700 (16)	0.75849 (18)	0.33679 (12)	0.0287 (6)
H2A	0.0728	0.7726	0.3565	0.034*
C3	0.15377 (16)	0.81698 (18)	0.21974 (12)	0.0300 (7)
C4	0.09725 (17)	0.78284 (19)	0.17878 (12)	0.0333 (7)
C5	0.0907 (2)	0.8165 (2)	0.13071 (14)	0.0444 (8)
H5A	0.0531	0.7938	0.1028	0.053*
C6	0.13718 (19)	0.8819 (2)	0.12255 (14)	0.0517 (10)
H6A	0.1318	0.9039	0.0893	0.062*
C7	0.1914 (2)	0.9151 (2)	0.16265 (15)	0.0494 (9)
H7A	0.2232	0.9606	0.1567	0.059*
C8	0.20147 (18)	0.8845 (2)	0.21175 (13)	0.0376 (8)
C9	0.26128 (19)	0.9252 (2)	0.25446 (16)	0.0487 (9)
H9A	0.2617	0.8930	0.2863	0.058*
C10	0.3407 (2)	0.9179 (3)	0.2458 (2)	0.0756 (16)
H10A	0.3523	0.8567	0.2414	0.113*
H10B	0.3783	0.9418	0.2751	0.113*
H10C	0.3423	0.9504	0.2153	0.113*
C11	0.2431 (2)	1.0204 (3)	0.26245 (18)	0.0624 (11)
H11A	0.1929	1.0244	0.2689	0.094*
H11B	0.2433	1.0539	0.2320	0.094*
H11C	0.2814	1.0439	0.2915	0.094*
C12	0.04300 (17)	0.71206 (19)	0.18585 (13)	0.0359 (7)
H12A	0.0628	0.6881	0.2208	0.043*
C13	0.0397 (2)	0.6368 (2)	0.14810 (15)	0.0544 (10)
H13A	0.0911	0.6147	0.1513	0.082*
H13B	0.0182	0.6578	0.1134	0.082*
H13C	0.0078	0.5902	0.1556	0.082*
C14	−0.03609 (19)	0.7484 (2)	0.18194 (16)	0.0532 (10)
H14A	−0.0325	0.7963	0.2061	0.080*
H14B	−0.0684	0.7026	0.1898	0.080*
H14C	−0.0581	0.7697	0.1474	0.080*
C15	0.13473 (16)	0.61857 (18)	0.37644 (12)	0.0291 (6)
C16	0.07189 (17)	0.56534 (19)	0.35457 (12)	0.0329 (7)
C17	0.0601 (2)	0.4920 (2)	0.38173 (15)	0.0482 (9)
H17A	0.0186	0.4546	0.3676	0.058*
C18	0.1076 (3)	0.4733 (3)	0.42855 (16)	0.0586 (11)
H18A	0.0995	0.4222	0.4459	0.070*
C19	0.1666 (2)	0.5273 (2)	0.45041 (14)	0.0506 (9)
H19A	0.1980	0.5139	0.4831	0.061*
C20	0.18147 (18)	0.6019 (2)	0.42554 (12)	0.0362 (7)
C21	0.24305 (19)	0.6649 (2)	0.45129 (12)	0.0403 (8)
H21A	0.2649	0.6904	0.4245	0.048*
C22	0.2082 (2)	0.7392 (3)	0.47484 (15)	0.0583 (11)
H22A	0.1667	0.7655	0.4489	0.087*
H22B	0.2471	0.7832	0.4882	0.087*
H22C	0.1886	0.7166	0.5025	0.087*
C23	0.3083 (2)	0.6230 (3)	0.49129 (15)	0.0630 (11)
H23A	0.3303	0.5758	0.4757	0.095*
H23B	0.2889	0.5997	0.5189	0.095*
H23C	0.3473	0.6667	0.5049	0.095*
C24	0.01653 (17)	0.5850 (2)	0.30430 (13)	0.0351 (7)
H24A	0.0403	0.6285	0.2861	0.042*
C25	−0.0048 (2)	0.5050 (2)	0.27030 (15)	0.0464 (9)
H25A	0.0413	0.4790	0.2646	0.070*
H25B	−0.0389	0.5222	0.2377	0.070*
H25C	−0.0304	0.4626	0.2869	0.070*
C26	−0.0562 (2)	0.6249 (2)	0.31290 (16)	0.0497 (9)
H26A	−0.0433	0.6765	0.3343	0.075*
H26B	−0.0814	0.5823	0.3297	0.075*
H26C	−0.0905	0.6412	0.2802	0.075*
C27	0.37043 (16)	0.46030 (18)	0.20108 (11)	0.0283 (6)
H27A	0.3743	0.4304	0.1714	0.034*
C28	0.43204 (16)	0.46895 (18)	0.24300 (11)	0.0285 (6)
H28A	0.4803	0.4457	0.2433	0.034*
C29	0.24730 (16)	0.50720 (19)	0.15721 (11)	0.0283 (6)
C30	0.25609 (18)	0.5725 (2)	0.12378 (12)	0.0344 (7)
C31	0.2010 (2)	0.5803 (2)	0.07764 (13)	0.0460 (9)
H31A	0.2062	0.6245	0.0545	0.055*
C32	0.1394 (2)	0.5258 (2)	0.06487 (13)	0.0516 (9)
H32A	0.1025	0.5325	0.0333	0.062*
C33	0.13153 (19)	0.4614 (2)	0.09806 (13)	0.0430 (8)
H33A	0.0892	0.4233	0.0889	0.052*
C34	0.18444 (17)	0.45078 (19)	0.14485 (12)	0.0329 (7)
C35	0.17501 (18)	0.3773 (2)	0.17941 (13)	0.0355 (7)
H35A	0.2073	0.3905	0.2142	0.043*
C36	0.2038 (2)	0.2920 (2)	0.16180 (15)	0.0502 (9)
H36A	0.2564	0.2994	0.1602	0.075*
H36B	0.1720	0.2767	0.1281	0.075*
H36C	0.2012	0.2457	0.1859	0.075*
C37	0.09336 (19)	0.3675 (2)	0.18277 (15)	0.0458 (9)
H37A	0.0761	0.4223	0.1942	0.069*
H37B	0.0908	0.3214	0.2070	0.069*
H37C	0.0607	0.3524	0.1493	0.069*
C38	0.32372 (18)	0.6347 (2)	0.13481 (13)	0.0368 (7)
H38A	0.3536	0.6250	0.1707	0.044*
C39	0.3758 (2)	0.6154 (3)	0.10037 (16)	0.0577 (10)
H39A	0.4188	0.6559	0.1082	0.086*
H39B	0.3473	0.6223	0.0648	0.086*
H39C	0.3948	0.5558	0.1061	0.086*
C40	0.2986 (2)	0.7296 (2)	0.12971 (14)	0.0490 (9)
H40A	0.2656	0.7410	0.1521	0.073*
H40B	0.2706	0.7414	0.0945	0.073*
H40C	0.3433	0.7673	0.1392	0.073*
C41	0.48895 (16)	0.54084 (18)	0.31973 (12)	0.0305 (7)
C42	0.53291 (16)	0.6055 (2)	0.30411 (13)	0.0355 (7)
C43	0.60213 (18)	0.6276 (2)	0.33735 (16)	0.0490 (9)
H43A	0.6333	0.6699	0.3274	0.059*
C44	0.6262 (2)	0.5894 (3)	0.38420 (17)	0.0582 (11)
H44A	0.6742	0.6045	0.4060	0.070*
C45	0.5811 (2)	0.5293 (2)	0.39982 (15)	0.0509 (10)
H45A	0.5977	0.5052	0.4329	0.061*
C46	0.51160 (17)	0.5033 (2)	0.36812 (12)	0.0352 (7)
C47	0.46645 (18)	0.4333 (2)	0.38578 (12)	0.0344 (7)
H47A	0.4147	0.4314	0.3617	0.041*
C48	0.5038 (2)	0.3447 (2)	0.38485 (14)	0.0466 (9)
H48A	0.5099	0.3336	0.3508	0.070*
H48B	0.4717	0.2995	0.3937	0.070*
H48C	0.5537	0.3442	0.4095	0.070*
C49	0.4573 (2)	0.4510 (3)	0.43872 (13)	0.0520 (9)
H49A	0.4334	0.5078	0.4392	0.078*
H49B	0.5073	0.4507	0.4632	0.078*
H49C	0.4254	0.4059	0.4478	0.078*
C50	0.50759 (18)	0.65330 (19)	0.25420 (13)	0.0358 (7)
H50A	0.4547	0.6341	0.2372	0.043*
C51	0.5571 (2)	0.6329 (2)	0.21852 (17)	0.0537 (10)
H51A	0.5579	0.5701	0.2131	0.081*
H51B	0.6089	0.6535	0.2336	0.081*
H51C	0.5364	0.6620	0.1859	0.081*
C52	0.5057 (2)	0.7517 (2)	0.26284 (15)	0.0451 (9)
H52A	0.4734	0.7642	0.2856	0.068*
H52B	0.4851	0.7809	0.2303	0.068*
H52C	0.5572	0.7726	0.2782	0.068*
C53	0.32147 (17)	0.33239 (18)	0.28926 (13)	0.0347 (7)
H53A	0.3755	0.3283	0.3084	0.042*	0.637 (11)
H53B	0.3178	0.3259	0.2526	0.042*	0.637 (11)
H53C	0.3772	0.3372	0.2950	0.042*	0.363 (11)
H53D	0.2990	0.3133	0.2539	0.042*	0.363 (11)
C54A	0.2745 (3)	0.2634 (3)	0.3068 (2)	0.0399 (16)*	0.637 (11)
H54A	0.3048	0.2104	0.3182	0.048*	0.637 (11)
H54B	0.2290	0.2480	0.2795	0.048*	0.637 (11)
C55A	0.2527 (4)	0.3075 (2)	0.3508 (2)	0.0470 (18)*	0.637 (11)
H55A	0.2075	0.2801	0.3578	0.056*	0.637 (11)
H55B	0.2951	0.3063	0.3820	0.056*	0.637 (11)
C54B	0.3016 (5)	0.2697 (5)	0.3268 (4)	0.038 (3)*	0.363 (11)
H54C	0.2989	0.2093	0.3141	0.045*	0.363 (11)
H54D	0.3391	0.2728	0.3603	0.045*	0.363 (11)
C55B	0.2242 (5)	0.3018 (2)	0.3298 (5)	0.041 (3)*	0.363 (11)
H55C	0.1837	0.2837	0.2998	0.049*	0.363 (11)
H55D	0.2118	0.2808	0.3610	0.049*	0.363 (11)
C56	0.2358 (2)	0.3993 (2)	0.33100 (16)	0.0473 (9)
H56A	0.1825	0.4045	0.3106	0.057*	0.637 (11)
H56B	0.2446	0.4413	0.3594	0.057*	0.637 (11)
H56C	0.1871	0.4297	0.3169	0.057*	0.363 (11)
H56D	0.2578	0.4197	0.3662	0.057*	0.363 (11)
N1	0.16121 (12)	0.78254 (14)	0.26992 (9)	0.0253 (5)
N2	0.15262 (12)	0.68918 (14)	0.34728 (9)	0.0244 (5)
N3	0.30513 (13)	0.49636 (14)	0.20455 (9)	0.0245 (5)
N4	0.42064 (12)	0.51140 (14)	0.28312 (9)	0.0252 (5)
O1	0.28868 (11)	0.41535 (12)	0.29936 (8)	0.0286 (4)
Cl1	0.29709 (4)	0.80183 (5)	0.36299 (3)	0.03575 (18)
Cl2	0.31971 (4)	0.68646 (4)	0.25774 (3)	0.02920 (16)
Cl3	0.18000 (4)	0.57077 (4)	0.25873 (3)	0.02682 (16)
Cl4	0.32064 (4)	0.58807 (4)	0.35821 (3)	0.02876 (16)
Cr1	0.23158 (2)	0.69493 (3)	0.309904 (17)	0.02299 (11)
Cr2	0.31100 (2)	0.53728 (3)	0.274554 (17)	0.02229 (11)
C58	0.1798 (3)	0.9680 (3)	0.4190 (2)	0.0871 (16)
H58A	0.2090	0.9778	0.4546	0.105*
H58B	0.2015	0.9166	0.4062	0.105*
Cl7	0.18933 (10)	1.05833 (14)	0.38280 (8)	0.1275 (7)
Cl8	0.08513 (7)	0.94725 (8)	0.41733 (5)	0.0792 (4)
C59	0.4061 (4)	−0.0072 (4)	0.4289 (3)	0.110 (2)
H59A	0.3688	−0.0406	0.4028	0.132*
H59B	0.4565	−0.0346	0.4334	0.132*
Cl9	0.40933 (11)	0.09914 (15)	0.40844 (8)	0.1363 (7)
Cl10	0.38101 (10)	−0.01068 (14)	0.48510 (6)	0.1197 (6)
C60	0.5119 (3)	0.2487 (3)	0.09401 (19)	0.0709 (13)
H60A	0.5653	0.2533	0.1144	0.085*
H60B	0.4897	0.1960	0.1051	0.085*
Cl11	0.46194 (10)	0.33895 (10)	0.10523 (6)	0.0983 (5)
Cl12	0.50985 (11)	0.23883 (15)	0.03107 (7)	0.1319 (7)
C61	0.2913 (4)	0.2102 (5)	0.4963 (3)	0.087 (2)	0.75
H61A	0.3457	0.2110	0.5149	0.105*	0.75
H61B	0.2874	0.1793	0.4639	0.105*	0.75
Cl13	0.26315 (18)	0.31482 (15)	0.48220 (9)	0.1267 (9)	0.75
Cl14	0.24382 (15)	0.1508 (2)	0.53092 (11)	0.1330 (9)	0.75
C57	0.0102 (3)	0.1422 (3)	0.0331 (3)	0.109 (3)	0.75
H57A	−0.0094	0.1213	−0.0022	0.130*	0.38
H57B	−0.0232	0.1190	0.0534	0.130*	0.38
H57C	−0.0165	0.1045	0.0047	0.130*	0.37
H57D	−0.0175	0.1388	0.0598	0.130*	0.37
Cl5	0.10128 (19)	0.10275 (16)	0.05752 (8)	0.1279 (9)	0.75
Cl6A	0.0066 (4)	0.2544 (2)	0.0336 (2)	0.0962 (17)	0.38
Cl6B	0.0067 (6)	0.2481 (3)	0.01156 (19)	0.114 (3)	0.37

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0267 (14)	0.0192 (13)	0.0375 (17)	0.0036 (11)	0.0057 (12)	−0.0012 (12)
C2	0.0257 (14)	0.0226 (14)	0.0375 (17)	0.0015 (11)	0.0079 (13)	−0.0053 (13)
C3	0.0302 (15)	0.0225 (14)	0.0378 (17)	0.0078 (12)	0.0097 (13)	0.0032 (12)
C4	0.0345 (16)	0.0287 (15)	0.0356 (17)	0.0083 (13)	0.0070 (14)	0.0018 (13)
C5	0.051 (2)	0.0391 (19)	0.0396 (19)	0.0096 (16)	0.0060 (16)	0.0052 (15)
C6	0.063 (2)	0.051 (2)	0.044 (2)	0.0118 (19)	0.0200 (19)	0.0166 (18)
C7	0.049 (2)	0.0405 (19)	0.063 (3)	0.0049 (16)	0.0222 (19)	0.0194 (18)
C8	0.0329 (16)	0.0277 (16)	0.052 (2)	0.0050 (13)	0.0106 (15)	0.0115 (15)
C9	0.0369 (18)	0.0398 (19)	0.064 (2)	−0.0119 (15)	0.0041 (17)	0.0189 (18)
C10	0.035 (2)	0.033 (2)	0.153 (5)	−0.0033 (16)	0.015 (2)	−0.003 (3)
C11	0.045 (2)	0.060 (3)	0.080 (3)	−0.0005 (18)	0.012 (2)	−0.013 (2)
C12	0.0362 (16)	0.0291 (16)	0.0370 (18)	0.0000 (13)	0.0003 (14)	−0.0013 (13)
C13	0.063 (2)	0.040 (2)	0.052 (2)	−0.0024 (18)	0.0002 (19)	−0.0084 (17)
C14	0.0385 (19)	0.048 (2)	0.070 (3)	0.0004 (16)	0.0084 (18)	0.0021 (19)
C15	0.0330 (15)	0.0246 (14)	0.0330 (16)	0.0058 (12)	0.0145 (13)	0.0014 (12)
C16	0.0364 (16)	0.0251 (15)	0.0417 (18)	0.0003 (12)	0.0180 (14)	−0.0017 (13)
C17	0.059 (2)	0.0343 (18)	0.057 (2)	−0.0086 (16)	0.0258 (19)	0.0038 (17)
C18	0.081 (3)	0.042 (2)	0.059 (3)	−0.001 (2)	0.028 (2)	0.0199 (19)
C19	0.064 (2)	0.049 (2)	0.040 (2)	0.0071 (19)	0.0140 (18)	0.0148 (17)
C20	0.0411 (17)	0.0339 (17)	0.0353 (18)	0.0079 (13)	0.0128 (14)	0.0031 (14)
C21	0.0426 (18)	0.0478 (19)	0.0281 (17)	0.0051 (15)	0.0049 (14)	−0.0005 (15)
C22	0.061 (2)	0.061 (3)	0.048 (2)	0.007 (2)	0.0053 (19)	−0.016 (2)
C23	0.053 (2)	0.082 (3)	0.046 (2)	0.011 (2)	−0.0017 (19)	0.007 (2)
C24	0.0346 (16)	0.0270 (15)	0.0449 (19)	−0.0076 (13)	0.0124 (14)	−0.0034 (14)
C25	0.0438 (19)	0.0405 (19)	0.056 (2)	−0.0106 (15)	0.0160 (17)	−0.0133 (17)
C26	0.0396 (19)	0.043 (2)	0.064 (2)	0.0000 (15)	0.0099 (18)	−0.0086 (18)
C27	0.0343 (15)	0.0219 (14)	0.0321 (16)	0.0007 (12)	0.0148 (13)	−0.0023 (12)
C28	0.0268 (14)	0.0226 (14)	0.0387 (17)	0.0043 (11)	0.0135 (13)	0.0016 (13)
C29	0.0310 (15)	0.0283 (15)	0.0254 (15)	0.0022 (12)	0.0068 (12)	−0.0032 (12)
C30	0.0400 (17)	0.0340 (16)	0.0309 (17)	0.0021 (13)	0.0123 (14)	0.0003 (13)
C31	0.054 (2)	0.049 (2)	0.0330 (18)	−0.0027 (17)	0.0092 (16)	0.0063 (16)
C32	0.052 (2)	0.063 (2)	0.0325 (19)	−0.0046 (18)	−0.0027 (16)	0.0019 (18)
C33	0.0412 (18)	0.0449 (19)	0.0382 (19)	−0.0081 (15)	0.0024 (15)	−0.0036 (16)
C34	0.0352 (16)	0.0320 (16)	0.0317 (17)	−0.0023 (13)	0.0091 (13)	−0.0064 (13)
C35	0.0378 (17)	0.0306 (16)	0.0373 (18)	−0.0057 (13)	0.0084 (14)	−0.0030 (14)
C36	0.058 (2)	0.0347 (19)	0.058 (2)	−0.0009 (16)	0.0138 (19)	−0.0044 (17)
C37	0.0424 (19)	0.044 (2)	0.052 (2)	−0.0117 (15)	0.0149 (17)	−0.0023 (17)
C38	0.0414 (17)	0.0353 (17)	0.0349 (17)	−0.0031 (14)	0.0122 (14)	0.0066 (14)
C39	0.063 (2)	0.058 (2)	0.062 (3)	−0.003 (2)	0.034 (2)	0.001 (2)
C40	0.061 (2)	0.0380 (19)	0.046 (2)	−0.0025 (17)	0.0093 (18)	0.0079 (16)
C41	0.0255 (14)	0.0257 (14)	0.0380 (17)	0.0048 (12)	0.0044 (13)	−0.0009 (13)
C42	0.0257 (15)	0.0305 (16)	0.050 (2)	0.0010 (12)	0.0099 (14)	0.0006 (14)
C43	0.0293 (17)	0.0399 (19)	0.073 (3)	−0.0046 (14)	0.0045 (17)	0.0051 (18)
C44	0.0334 (18)	0.054 (2)	0.073 (3)	−0.0071 (17)	−0.0111 (18)	−0.001 (2)
C45	0.0426 (19)	0.048 (2)	0.050 (2)	0.0053 (16)	−0.0097 (17)	0.0042 (18)
C46	0.0328 (16)	0.0322 (16)	0.0372 (18)	0.0083 (13)	0.0030 (14)	0.0011 (14)
C47	0.0375 (16)	0.0321 (16)	0.0300 (16)	0.0071 (13)	0.0024 (13)	0.0047 (13)
C48	0.052 (2)	0.0364 (18)	0.046 (2)	0.0121 (16)	0.0040 (17)	0.0030 (16)
C49	0.063 (2)	0.053 (2)	0.037 (2)	0.0117 (18)	0.0082 (18)	0.0021 (17)
C50	0.0317 (16)	0.0276 (16)	0.050 (2)	0.0001 (13)	0.0139 (14)	0.0021 (14)
C51	0.053 (2)	0.045 (2)	0.073 (3)	0.0095 (17)	0.034 (2)	0.012 (2)
C52	0.0410 (18)	0.0303 (17)	0.064 (2)	−0.0002 (14)	0.0132 (17)	0.0022 (16)
C53	0.0394 (17)	0.0208 (14)	0.0463 (19)	0.0051 (12)	0.0155 (15)	0.0010 (13)
C56	0.056 (2)	0.0370 (19)	0.062 (2)	0.0029 (16)	0.0383 (19)	0.0086 (17)
N1	0.0235 (11)	0.0173 (11)	0.0332 (13)	0.0006 (9)	0.0039 (10)	0.0007 (10)
N2	0.0236 (11)	0.0206 (11)	0.0277 (12)	−0.0004 (9)	0.0045 (10)	−0.0035 (10)
N3	0.0274 (12)	0.0202 (11)	0.0270 (13)	−0.0020 (9)	0.0089 (10)	−0.0008 (10)
N4	0.0242 (11)	0.0202 (11)	0.0310 (13)	0.0022 (9)	0.0069 (10)	0.0030 (10)
O1	0.0327 (10)	0.0211 (10)	0.0356 (11)	0.0031 (8)	0.0153 (9)	0.0027 (9)
Cl1	0.0334 (4)	0.0273 (4)	0.0410 (4)	−0.0039 (3)	−0.0003 (3)	−0.0055 (3)
Cl2	0.0301 (3)	0.0215 (3)	0.0385 (4)	0.0020 (3)	0.0135 (3)	0.0032 (3)
Cl3	0.0232 (3)	0.0227 (3)	0.0333 (4)	0.0014 (3)	0.0052 (3)	−0.0037 (3)
Cl4	0.0309 (3)	0.0269 (3)	0.0268 (4)	0.0074 (3)	0.0046 (3)	0.0000 (3)
Cr1	0.0216 (2)	0.0182 (2)	0.0281 (2)	0.00189 (17)	0.00455 (18)	−0.00073 (18)
Cr2	0.0223 (2)	0.0185 (2)	0.0265 (2)	0.00255 (17)	0.00712 (18)	0.00039 (18)
C58	0.063 (3)	0.075 (3)	0.111 (4)	0.007 (2)	0.001 (3)	0.001 (3)
Cl7	0.1034 (12)	0.1551 (17)	0.1255 (14)	−0.0021 (11)	0.0324 (11)	0.0440 (13)
Cl8	0.0656 (7)	0.0764 (8)	0.0899 (9)	0.0062 (6)	0.0102 (6)	−0.0126 (7)
C59	0.098 (4)	0.098 (4)	0.137 (6)	−0.005 (3)	0.034 (4)	−0.048 (4)
Cl9	0.1284 (14)	0.1613 (18)	0.1273 (15)	−0.0241 (13)	0.0480 (12)	0.0590 (13)
Cl10	0.1108 (12)	0.1592 (16)	0.0853 (10)	−0.0175 (11)	0.0189 (9)	0.0503 (11)
C60	0.055 (2)	0.060 (3)	0.095 (4)	−0.003 (2)	0.015 (2)	0.004 (3)
Cl11	0.1274 (12)	0.0849 (9)	0.0944 (10)	0.0328 (8)	0.0499 (9)	0.0142 (8)
Cl12	0.1228 (13)	0.1706 (18)	0.1001 (12)	0.0383 (13)	0.0251 (10)	−0.0424 (12)
C61	0.078 (4)	0.091 (5)	0.099 (5)	0.002 (4)	0.035 (4)	0.013 (4)
Cl13	0.186 (3)	0.0968 (15)	0.0962 (15)	0.0382 (16)	0.0347 (16)	0.0019 (12)
Cl14	0.134 (2)	0.156 (2)	0.140 (2)	−0.0201 (17)	0.0911 (18)	0.0088 (18)
C57	0.109 (6)	0.147 (8)	0.081 (5)	−0.062 (6)	0.045 (5)	0.006 (5)
Cl5	0.218 (3)	0.1073 (16)	0.0804 (13)	0.0387 (17)	0.0786 (17)	0.0059 (12)
Cl6A	0.085 (3)	0.091 (3)	0.104 (5)	−0.013 (2)	0.009 (4)	−0.027 (2)
Cl6B	0.145 (5)	0.133 (5)	0.061 (3)	−0.024 (4)	0.020 (4)	−0.017 (3)

Geometric parameters (Å, º) top

C1—N1	1.336 (4)	C39—H39B	0.9800
C1—C2	1.386 (4)	C39—H39C	0.9800
C1—H1A	0.9500	C40—H40A	0.9800
C2—N2	1.339 (3)	C40—H40B	0.9800
C2—H2A	0.9500	C40—H40C	0.9800
C3—C8	1.410 (4)	C41—C46	1.402 (4)
C3—C4	1.410 (4)	C41—C42	1.413 (4)
C3—N1	1.443 (4)	C41—N4	1.452 (4)
C4—C5	1.388 (5)	C42—C43	1.392 (4)
C4—C12	1.519 (4)	C42—C50	1.512 (5)
C5—C6	1.372 (4)	C43—C44	1.372 (6)
C5—H5A	0.9500	C43—H43A	0.9500
C6—C7	1.369 (4)	C44—C45	1.379 (6)
C6—H6A	0.9500	C44—H44A	0.9500
C7—C8	1.388 (5)	C45—C46	1.395 (4)
C7—H7A	0.9500	C45—H45A	0.9500
C8—C9	1.510 (5)	C46—C47	1.512 (5)
C9—C11	1.532 (5)	C47—C49	1.523 (5)
C9—C10	1.534 (5)	C47—C48	1.530 (4)
C9—H9A	1.0000	C47—H47A	1.0000
C10—H10A	0.9800	C48—H48A	0.9800
C10—H10B	0.9800	C48—H48B	0.9800
C10—H10C	0.9800	C48—H48C	0.9800
C11—H11A	0.9800	C49—H49A	0.9800
C11—H11B	0.9800	C49—H49B	0.9800
C11—H11C	0.9800	C49—H49C	0.9800
C12—C14	1.526 (5)	C50—C51	1.526 (5)
C12—C13	1.542 (5)	C50—C52	1.536 (4)
C12—H12A	1.0000	C50—H50A	1.0000
C13—H13A	0.9800	C51—H51A	0.9800
C13—H13B	0.9800	C51—H51B	0.9800
C13—H13C	0.9800	C51—H51C	0.9800
C14—H14A	0.9800	C52—H52A	0.9800
C14—H14B	0.9800	C52—H52B	0.9800
C14—H14C	0.9800	C52—H52C	0.9800
C15—C16	1.410 (4)	C53—O1	1.468 (3)
C15—C20	1.412 (4)	C53—C54A	1.519 (3)
C15—N2	1.436 (4)	C53—C54B	1.520 (3)
C16—C17	1.399 (5)	C53—H53A	0.9900
C16—C24	1.508 (4)	C53—H53B	0.9900
C17—C18	1.375 (6)	C53—H53C	0.9900
C17—H17A	0.9500	C53—H53D	0.9900
C18—C19	1.368 (6)	C54A—C55A	1.520 (3)
C18—H18A	0.9500	C54A—H54A	0.9900
C19—C20	1.397 (5)	C54A—H54B	0.9900
C19—H19A	0.9500	C55A—C56	1.518 (3)
C20—C21	1.513 (5)	C55A—H55A	0.9900
C21—C22	1.531 (5)	C55A—H55B	0.9900
C21—C23	1.532 (5)	C54B—C55B	1.520 (3)
C21—H21A	1.0000	C54B—H54C	0.9900
C22—H22A	0.9800	C54B—H54D	0.9900
C22—H22B	0.9800	C55B—C56	1.518 (3)
C22—H22C	0.9800	C55B—H55C	0.9900
C23—H23A	0.9800	C55B—H55D	0.9900
C23—H23B	0.9800	C56—O1	1.475 (4)
C23—H23C	0.9800	C56—H56A	0.9900
C24—C25	1.531 (4)	C56—H56B	0.9900
C24—C26	1.536 (5)	C56—H56C	0.9900
C24—H24A	1.0000	C56—H56D	0.9900
C25—H25A	0.9800	N1—Cr1	1.983 (2)
C25—H25B	0.9800	N2—Cr1	1.974 (2)
C25—H25C	0.9800	N3—Cr2	1.989 (2)
C26—H26A	0.9800	N4—Cr2	1.994 (2)
C26—H26B	0.9800	O1—Cr2	2.0737 (19)
C26—H26C	0.9800	Cl1—Cr1	2.3107 (8)
C27—N3	1.341 (4)	Cl2—Cr2	2.3579 (8)
C27—C28	1.386 (4)	Cl2—Cr1	2.4153 (9)
C27—H27A	0.9500	Cl3—Cr2	2.3730 (8)
C28—N4	1.338 (4)	Cl3—Cr1	2.4110 (8)
C28—H28A	0.9500	Cl4—Cr2	2.3778 (8)
C29—C30	1.395 (4)	Cl4—Cr1	2.4441 (8)
C29—C34	1.409 (4)	C58—Cl7	1.742 (6)
C29—N3	1.449 (4)	C58—Cl8	1.747 (5)
C30—C31	1.397 (5)	C58—H58A	0.9900
C30—C38	1.530 (4)	C58—H58B	0.9900
C31—C32	1.373 (4)	C59—Cl10	1.714 (7)
C31—H31A	0.9500	C59—Cl9	1.738 (7)
C32—C33	1.377 (4)	C59—H59A	0.9900
C32—H32A	0.9500	C59—H59B	0.9900
C33—C34	1.395 (4)	C60—Cl12	1.716 (5)
C33—H33A	0.9500	C60—Cl11	1.733 (5)
C34—C35	1.513 (4)	C60—H60A	0.9900
C35—C37	1.525 (5)	C60—H60B	0.9900
C35—C36	1.537 (5)	C61—Cl13	1.705 (7)
C35—H35A	1.0000	C61—Cl14	1.708 (7)
C36—H36A	0.9800	C61—H61A	0.9900
C36—H36B	0.9800	C61—H61B	0.9900
C36—H36C	0.9800	C57—Cl6A	1.730 (5)
C37—H37A	0.9800	C57—Cl6B	1.731 (5)
C37—H37B	0.9800	C57—Cl5	1.732 (4)
C37—H37C	0.9800	C57—H57A	0.9900
C38—C40	1.529 (5)	C57—H57B	0.9900
C38—C39	1.532 (5)	C57—H57C	0.9900
C38—H38A	1.0000	C57—H57D	0.9900
C39—H39A	0.9800

N1—C1—C2	117.2 (2)	C45—C46—C41	117.6 (3)
N1—C1—H1A	121.4	C45—C46—C47	119.4 (3)
C2—C1—H1A	121.4	C41—C46—C47	123.0 (3)
N2—C2—C1	116.6 (3)	C46—C47—C49	112.3 (3)
N2—C2—H2A	121.7	C46—C47—C48	110.5 (3)
C1—C2—H2A	121.7	C49—C47—C48	109.6 (3)
C8—C3—C4	120.4 (3)	C46—C47—H47A	108.1
C8—C3—N1	120.7 (3)	C49—C47—H47A	108.1
C4—C3—N1	118.9 (3)	C48—C47—H47A	108.1
C5—C4—C3	118.4 (3)	C47—C48—H48A	109.5
C5—C4—C12	119.4 (3)	C47—C48—H48B	109.5
C3—C4—C12	122.2 (3)	H48A—C48—H48B	109.5
C6—C5—C4	121.6 (3)	C47—C48—H48C	109.5
C6—C5—H5A	119.2	H48A—C48—H48C	109.5
C4—C5—H5A	119.2	H48B—C48—H48C	109.5
C7—C6—C5	119.6 (3)	C47—C49—H49A	109.5
C7—C6—H6A	120.2	C47—C49—H49B	109.5
C5—C6—H6A	120.2	H49A—C49—H49B	109.5
C6—C7—C8	122.0 (3)	C47—C49—H49C	109.5
C6—C7—H7A	119.0	H49A—C49—H49C	109.5
C8—C7—H7A	119.0	H49B—C49—H49C	109.5
C7—C8—C3	118.0 (3)	C42—C50—C51	112.5 (3)
C7—C8—C9	119.4 (3)	C42—C50—C52	110.9 (3)
C3—C8—C9	122.6 (3)	C51—C50—C52	110.0 (3)
C8—C9—C11	111.6 (3)	C42—C50—H50A	107.7
C8—C9—C10	111.8 (4)	C51—C50—H50A	107.7
C11—C9—C10	110.0 (3)	C52—C50—H50A	107.7
C8—C9—H9A	107.7	C50—C51—H51A	109.5
C11—C9—H9A	107.7	C50—C51—H51B	109.5
C10—C9—H9A	107.7	H51A—C51—H51B	109.5
C9—C10—H10A	109.5	C50—C51—H51C	109.5
C9—C10—H10B	109.5	H51A—C51—H51C	109.5
H10A—C10—H10B	109.5	H51B—C51—H51C	109.5
C9—C10—H10C	109.5	C50—C52—H52A	109.5
H10A—C10—H10C	109.5	C50—C52—H52B	109.5
H10B—C10—H10C	109.5	H52A—C52—H52B	109.5
C9—C11—H11A	109.5	C50—C52—H52C	109.5
C9—C11—H11B	109.5	H52A—C52—H52C	109.5
H11A—C11—H11B	109.5	H52B—C52—H52C	109.5
C9—C11—H11C	109.5	O1—C53—C54A	105.0 (3)
H11A—C11—H11C	109.5	O1—C53—C54B	104.3 (4)
H11B—C11—H11C	109.5	O1—C53—H53A	110.8
C4—C12—C14	111.3 (3)	C54A—C53—H53A	110.8
C4—C12—C13	111.6 (3)	C54B—C53—H53A	89.0
C14—C12—C13	111.0 (3)	O1—C53—H53B	110.8
C4—C12—H12A	107.6	C54A—C53—H53B	110.8
C14—C12—H12A	107.6	C54B—C53—H53B	130.7
C13—C12—H12A	107.6	H53A—C53—H53B	108.8
C12—C13—H13A	109.5	O1—C53—H53C	110.9
C12—C13—H13B	109.5	C54A—C53—H53C	130.0
H13A—C13—H13B	109.5	C54B—C53—H53C	110.9
C12—C13—H13C	109.5	H53B—C53—H53C	87.9
H13A—C13—H13C	109.5	O1—C53—H53D	110.9
H13B—C13—H13C	109.5	C54A—C53—H53D	88.6
C12—C14—H14A	109.5	C54B—C53—H53D	110.9
C12—C14—H14B	109.5	H53A—C53—H53D	126.8
H14A—C14—H14B	109.5	H53C—C53—H53D	108.9
C12—C14—H14C	109.5	C53—C54A—C55A	102.9 (3)
H14A—C14—H14C	109.5	C53—C54A—H54A	111.2
H14B—C14—H14C	109.5	C55A—C54A—H54A	111.2
C16—C15—C20	121.3 (3)	C53—C54A—H54B	111.2
C16—C15—N2	118.9 (3)	C55A—C54A—H54B	111.2
C20—C15—N2	119.8 (3)	H54A—C54A—H54B	109.1
C17—C16—C15	117.8 (3)	C56—C55A—C54A	101.9 (4)
C17—C16—C24	119.1 (3)	C56—C55A—H55A	111.4
C15—C16—C24	123.1 (3)	C54A—C55A—H55A	111.4
C18—C17—C16	121.0 (3)	C56—C55A—H55B	111.4
C18—C17—H17A	119.5	C54A—C55A—H55B	111.4
C16—C17—H17A	119.5	H55A—C55A—H55B	109.3
C19—C18—C17	120.7 (3)	C55B—C54B—C53	102.7 (5)
C19—C18—H18A	119.6	C55B—C54B—H54C	111.2
C17—C18—H18A	119.6	C53—C54B—H54C	111.2
C18—C19—C20	121.3 (3)	C55B—C54B—H54D	111.2
C18—C19—H19A	119.4	C53—C54B—H54D	111.2
C20—C19—H19A	119.4	H54C—C54B—H54D	109.1
C19—C20—C15	117.7 (3)	C56—C55B—C54B	101.3 (5)
C19—C20—C21	121.2 (3)	C56—C55B—H55C	111.5
C15—C20—C21	121.0 (3)	C54B—C55B—H55C	111.5
C20—C21—C22	109.6 (3)	C56—C55B—H55D	111.5
C20—C21—C23	113.9 (3)	C54B—C55B—H55D	111.5
C22—C21—C23	110.3 (3)	H55C—C55B—H55D	109.3
C20—C21—H21A	107.6	O1—C56—C55A	105.2 (3)
C22—C21—H21A	107.6	O1—C56—C55B	105.2 (4)
C23—C21—H21A	107.6	O1—C56—H56A	110.7
C21—C22—H22A	109.5	C55A—C56—H56A	110.7
C21—C22—H22B	109.5	C55B—C56—H56A	87.5
H22A—C22—H22B	109.5	O1—C56—H56B	110.7
C21—C22—H22C	109.5	C55A—C56—H56B	110.7
H22A—C22—H22C	109.5	C55B—C56—H56B	131.1
H22B—C22—H22C	109.5	H56A—C56—H56B	108.8
C21—C23—H23A	109.5	O1—C56—H56C	110.7
C21—C23—H23B	109.5	C55A—C56—H56C	131.1
H23A—C23—H23B	109.5	C55B—C56—H56C	110.7
C21—C23—H23C	109.5	H56B—C56—H56C	86.5
H23A—C23—H23C	109.5	O1—C56—H56D	110.7
H23B—C23—H23C	109.5	C55A—C56—H56D	87.5
C16—C24—C25	113.2 (3)	C55B—C56—H56D	110.7
C16—C24—C26	110.0 (3)	H56A—C56—H56D	127.7
C25—C24—C26	108.8 (3)	H56C—C56—H56D	108.8
C16—C24—H24A	108.3	C1—N1—C3	118.7 (2)
C25—C24—H24A	108.3	C1—N1—Cr1	109.93 (19)
C26—C24—H24A	108.3	C3—N1—Cr1	131.32 (19)
C24—C25—H25A	109.5	C2—N2—C15	120.3 (2)
C24—C25—H25B	109.5	C2—N2—Cr1	110.54 (19)
H25A—C25—H25B	109.5	C15—N2—Cr1	128.58 (18)
C24—C25—H25C	109.5	C27—N3—C29	116.0 (2)
H25A—C25—H25C	109.5	C27—N3—Cr2	111.96 (19)
H25B—C25—H25C	109.5	C29—N3—Cr2	131.64 (18)
C24—C26—H26A	109.5	C28—N4—C41	115.3 (2)
C24—C26—H26B	109.5	C28—N4—Cr2	111.59 (18)
H26A—C26—H26B	109.5	C41—N4—Cr2	132.33 (19)
C24—C26—H26C	109.5	C53—O1—C56	109.0 (2)
H26A—C26—H26C	109.5	C53—O1—Cr2	127.10 (16)
H26B—C26—H26C	109.5	C56—O1—Cr2	123.88 (16)
N3—C27—C28	116.5 (3)	Cr2—Cl2—Cr1	81.29 (3)
N3—C27—H27A	121.8	Cr2—Cl3—Cr1	81.07 (2)
C28—C27—H27A	121.8	Cr2—Cl4—Cr1	80.30 (3)
N4—C28—C27	117.2 (2)	N2—Cr1—N1	81.95 (10)
N4—C28—H28A	121.4	N2—Cr1—Cl1	92.03 (7)
C27—C28—H28A	121.4	N1—Cr1—Cl1	90.83 (7)
C30—C29—C34	120.9 (3)	N2—Cr1—Cl3	92.11 (7)
C30—C29—N3	119.0 (3)	N1—Cr1—Cl3	97.04 (7)
C34—C29—N3	120.0 (3)	Cl1—Cr1—Cl3	171.55 (3)
C29—C30—C31	118.3 (3)	N2—Cr1—Cl2	172.58 (7)
C29—C30—C38	123.2 (3)	N1—Cr1—Cl2	98.48 (8)
C31—C30—C38	118.5 (3)	Cl1—Cr1—Cl2	95.36 (3)
C32—C31—C30	121.6 (3)	Cl3—Cr1—Cl2	80.48 (3)
C32—C31—H31A	119.2	N2—Cr1—Cl4	99.39 (7)
C30—C31—H31A	119.2	N1—Cr1—Cl4	178.63 (8)
C31—C32—C33	119.6 (3)	Cl1—Cr1—Cl4	88.84 (3)
C31—C32—H32A	120.2	Cl3—Cr1—Cl4	83.22 (3)
C33—C32—H32A	120.2	Cl2—Cr1—Cl4	80.24 (3)
C32—C33—C34	121.4 (3)	N3—Cr2—N4	81.34 (10)
C32—C33—H33A	119.3	N3—Cr2—O1	93.49 (9)
C34—C33—H33A	119.3	N4—Cr2—O1	93.29 (8)
C33—C34—C29	118.2 (3)	N3—Cr2—Cl2	96.39 (7)
C33—C34—C35	119.6 (3)	N4—Cr2—Cl2	95.80 (7)
C29—C34—C35	122.1 (3)	O1—Cr2—Cl2	167.46 (6)
C34—C35—C37	112.6 (3)	N3—Cr2—Cl3	95.48 (7)
C34—C35—C36	109.9 (3)	N4—Cr2—Cl3	176.21 (8)
C37—C35—C36	110.7 (3)	O1—Cr2—Cl3	88.96 (6)
C34—C35—H35A	107.8	Cl2—Cr2—Cl3	82.45 (3)
C37—C35—H35A	107.8	N3—Cr2—Cl4	178.65 (7)
C36—C35—H35A	107.8	N4—Cr2—Cl4	97.66 (7)
C35—C36—H36A	109.5	O1—Cr2—Cl4	87.47 (6)
C35—C36—H36B	109.5	Cl2—Cr2—Cl4	82.78 (3)
H36A—C36—H36B	109.5	Cl3—Cr2—Cl4	85.48 (3)
C35—C36—H36C	109.5	Cl7—C58—Cl8	112.1 (3)
H36A—C36—H36C	109.5	Cl7—C58—H58A	109.2
H36B—C36—H36C	109.5	Cl8—C58—H58A	109.2
C35—C37—H37A	109.5	Cl7—C58—H58B	109.2
C35—C37—H37B	109.5	Cl8—C58—H58B	109.2
H37A—C37—H37B	109.5	H58A—C58—H58B	107.9
C35—C37—H37C	109.5	Cl10—C59—Cl9	110.9 (3)
H37A—C37—H37C	109.5	Cl10—C59—H59A	109.5
H37B—C37—H37C	109.5	Cl9—C59—H59A	109.5
C40—C38—C30	112.0 (3)	Cl10—C59—H59B	109.5
C40—C38—C39	110.4 (3)	Cl9—C59—H59B	109.5
C30—C38—C39	110.9 (3)	H59A—C59—H59B	108.0
C40—C38—H38A	107.8	Cl12—C60—Cl11	112.0 (3)
C30—C38—H38A	107.8	Cl12—C60—H60A	109.2
C39—C38—H38A	107.8	Cl11—C60—H60A	109.2
C38—C39—H39A	109.5	Cl12—C60—H60B	109.2
C38—C39—H39B	109.5	Cl11—C60—H60B	109.2
H39A—C39—H39B	109.5	H60A—C60—H60B	107.9
C38—C39—H39C	109.5	Cl13—C61—Cl14	117.7 (5)
H39A—C39—H39C	109.5	Cl13—C61—H61A	107.9
H39B—C39—H39C	109.5	Cl14—C61—H61A	107.9
C38—C40—H40A	109.5	Cl13—C61—H61B	107.9
C38—C40—H40B	109.5	Cl14—C61—H61B	107.9
H40A—C40—H40B	109.5	H61A—C61—H61B	107.2
C38—C40—H40C	109.5	Cl6A—C57—Cl5	112.5 (5)
H40A—C40—H40C	109.5	Cl6B—C57—Cl5	114.1 (5)
H40B—C40—H40C	109.5	Cl6A—C57—H57A	109.1
C46—C41—C42	121.6 (3)	Cl6B—C57—H57A	90.2
C46—C41—N4	120.6 (3)	Cl5—C57—H57A	109.1
C42—C41—N4	117.8 (3)	Cl6A—C57—H57B	109.1
C43—C42—C41	117.8 (3)	Cl6B—C57—H57B	123.9
C43—C42—C50	118.7 (3)	Cl5—C57—H57B	109.1
C41—C42—C50	123.5 (3)	H57A—C57—H57B	107.8
C44—C43—C42	121.2 (3)	Cl6A—C57—H57C	125.5
C44—C43—H43A	119.4	Cl6B—C57—H57C	108.7
C42—C43—H43A	119.4	Cl5—C57—H57C	108.7
C43—C44—C45	120.3 (3)	H57B—C57—H57C	88.6
C43—C44—H44A	119.8	Cl6A—C57—H57D	91.2
C45—C44—H44A	119.8	Cl6B—C57—H57D	108.7
C44—C45—C46	121.4 (3)	Cl5—C57—H57D	108.7
C44—C45—H45A	119.3	H57A—C57—H57D	125.0
C46—C45—H45A	119.3	H57C—C57—H57D	107.6

Experimental details

Crystal data
Chemical formula	[Cr₂Cl₄(C₂₆H₃₆N₂)₂(C₄H₈O)]·4.5CH₂Cl₂
M_r	1453.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	18.2545 (6), 15.4111 (4), 27.3121 (7)
β (°)	105.160 (2)
V (Å³)	7416.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.50 × 0.50 × 0.37

Data collection
Diffractometer	STOE IPDS II diffractometer
Absorption correction	Numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)
T_min, T_max	0.672, 0.810
No. of measured, independent and observed [I > 2σ(I)] reflections	94968, 13785, 9450
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.123, 0.93
No. of reflections	13785
No. of parameters	747
No. of restraints	20
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.57

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Leibniz-Institut für Katalyse e. V. an der Universität Rostock.

References

Dietel, A. M., Irrgang, T., Karthikeyan, S. & Kempe, R. (2006). Z. Kristallogr. New Cryst. Struct. 221, 547–550. CAS Google Scholar
Kreisel, K. A., Yap, G. P. A., Dmitrenko, O., Landis, C. R. & Theopold, K. H. (2007). J. Am. Chem. Soc. 129, 14162–14163. Web of Science CSD CrossRef PubMed CAS Google Scholar
Kreisel, K. A., Yap, G. P. A. & Theopold, K. H. (2008). Inorg. Chem. 47, 5293–5303. Web of Science CSD CrossRef PubMed CAS Google Scholar
Peitz, S., Peulecke, N., Müller, B. H., Spannenberg, A. & Rosenthal, U. (2009). Acta Cryst. E65, m1336. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany. Google Scholar
Wagner, F. R., Noor, A. & Kempe, R. (2009). Nat. Chem. 1, 529–536. Web of Science CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.