The first metalloporphyrin dimer linked by a bridging phenylenedicarbene ligand

In the first bis­[ruthenium(II)–porphyrin]–dicarbene complex, μ-[1,4-phenyl­ene­bis(phenyl­methyl­idene-κC)]bis­[(ethanol-κO)(5,10,15,20-tetra-p-tolyl­porphyrinato-κ⁴N)ruthenium(II)] 1,2-di­chloro­ethane trisolvate, [Ru₂(C₂₀H₁₄)(C₄₈H₃₆N₄)₂(C₂H₆O)₂]·3C₂H₄Cl₂, an inversion center is located at the center of the μ-phenyl­ene group, leading to a parallel arrangement for the pair of porphyrin ring systems. The bond lengths and angles compare favourably with literature values for ruthenium–porphyrin–monocarbene complexes; the Ru=C(carbene) bond length and the C(phenyl)—C(carbene)—C(phenyl­ene) angle are 1.865 (3) Å and 112.3 (3)°, respectively. The Ru^II ion is displaced out of the C₂₀N₄ porphyrin least-squares plane (by 0.2373 Å) toward the bridging ligand of the C_i-symmetry dimer. The porphyrin ring systems of the dimer thus exhibit mildly domed conformations.

S1. Comment

A number of ruthenium(II)–porphyrin–carbene complexes, which are fairly stable in air at room temperature, have been developed in the past decade. Our group has structurally characterized some of these compounds, namely a methanol-bonded diphenylcarbene complex [Ru(ttp)(═CPh₂)(MeOH)]·MeOH (H₂ttp is 5,10,15,20-tetra-p-tolylporphyrin; Kawai et al., 2002), six-coordinate pyridine adducts [Ru(ttp)(═CR₂)(py)] (R = COPh and m-C₆H₄CF₃; Harada et al., 2003) and a five-coordinate complex [Ru(ttp){═C(m-C₆H₄CF₃)₂}] (Wada et al., 2003). These carbene ligands were generally prepared from ketones via hydrazone and diazomethylene compounds. According to analogous procedures, some µ-phenylene-bridging dicarbene complexes have already been synthesized (Herrmann et al., 1984; Werner et al., 1997), but their structural features have not been reported so far. In order to investigate structural details of the dicarbene complex, we have carried out a synthesis and structure determination of the first metalloporphyrin dimer linked by a µ-phenylene-bridging dicarbene ligand.

As shown in Figs. 1 and 2, an inversion center positioned at the centroid of the µ-phenylene group of the centrosymmetric bis[ruthenium(II)–porphyrin]–dicarbene complex (I) effects a parallel arrangement for the pair of porphyrin groups. The asymmetric unit includes one-half of the binuclear molecule and 1.5 molecules of 1,2-dichloroethane solvent. The bond lengths and angles in (I) are comparable to literature data for ruthenium porphyrin monocarbene complexes reported to date (Li et al., 2004). The geometry about the Ru and the carbene C atoms in (I) is similar to that reported for [Ru(ttp)(═CPh₂)(MeOH)]·MeOH, (II) (Kawai et al., 2002). Moreover, the six-coordinate Ru atom is bonded by the hydroxy O atom of an ethanol ligand trans to the carbene C atom in each of (I) and (II). The Ru—O bond length of 2.417 (3) Å in (I) is longer than that of 2.362 (3) Å in (II). The carbene angle [C50—C49—C56] of 112.3 (3)° in (I) is very close to that of 112.2 (3)° in (II). The Ru═ C(carbene) bond length [Ru═C49] of 1.865 (3) Å in (I) is slightly longer than that of 1.845 (3) Å in (II).

The phenyl groups of (I) are connected to the carbene donor C atoms and tilted relative to the phenylene group of the dicarbene ligand, while the phenylene group itself is oriented almost perpendicular to the carbene plane (Table 1), consistent with the phenyl group arrangements in (II). The torsion angles in (I) about the C(carbene)—C(phenyl) and the C(carbene)—C(phenylene) formal single bonds are considerably larger than the corresponding angles 23.5 (5) and 36.9 (5)° in 1,4-dibenzoylbenzene (Kolev et al., 1992), and 30.5 (2) and 39.5 (2)° in 1,4-bis(phenylvinyl)benzene (Klokkenburg et al., 2003) bearing 1,4-phenylenebis(phenylmethylidene) skeletons. The tilted phenyl group in (I) seems to repel the C21–C27 p-tolyl group of the opposite porphyrin. The dihedral angles between the porphyrin C₂₀N₄ core and the p-tolyl groups in (I) and (II) are within their usual ranges, viz. 81.05 (13), 63.14 (16), 66.66 (13) and 79.56 (13)° in (I), and 64.80 (8), 61.31 (10), 75.19 (11) and 88.44 (14)° in (II). As the Ru^II ion is displaced out of the least-squares plane toward the carbene C atom by 0.2373 (8) Å in (I), the porphyrin core is deformed in a dome conformation, with maximum and minimum deviations from the C₂₀N₄ least-squares plane of 0.187 (4) and −0.301 (4) Å for C8 and C13, respectively. In (I), there are some noteworthy van der Waals contacts, such as intramolecular interactions C23—H10···C54ⁱ and C55—H41···C14 and intermolecular interactions C46—H32···C15ⁱⁱ and Cl2···Cl3ⁱⁱⁱ (symmetry codes and contact distances are given in Table 1). One final contact is the short O—H44···C46ⁱⁱ distance which apparently reflects a distinct O—H···π(arene) interaction (Table 2).

S2. Experimental

The dicarbene precursor, 1,4-bis(diazobenzyl)benzene, was prepared according to the method of Murray & Trozzolo (1961). A solution of [(ttp)Ru(CO)] (144 mg, 180 µmol) and 1,4-bis(diazobenzyl)benzene (23 mg, 74 µmol) in n-octane (50 ml) was refluxed under nitrogen atmosphere for 3 h. After removal of the volatiles in vacuo, the residue was chromatographed on a silica-gel column with CH₂Cl₂/n-hexane mixture (v/v 2:1). An intense red band was collected and evaporated to dryness. Recrystallization from a 1,2-dichloroethane/ethanol solution gave air-stable dark-red crystals of (I) (yield 80%). ¹H NMR (CDCl₃, 400 MHz, p.p.m.): δ 1.79 (s, 4H), 2.52 (s, 24H), 2.84 (d, J = 7.2 Hz, 4H), 6.19 (t, J = 7.8 Hz, 4H), 6.54 (t, J = 7.2 Hz, 2H), 7.09–7.16 (m, 16H), 7.27 (d, J = 8.1 Hz, 8H), 7.64 (d, J = 6.4 Hz, 8H), 7.91 (s, 16H). UV–vis (CH₂Cl₂): λ_max (log ε) 397 (5.34), 427 (5.15), 532 (4.38). An analogous dicarbene complex, [{(ttp)Ru}₂{(═CCF₃)₂(C₆H₄)}], was successfully synthesized in 50% yield, starting from [(ttp)Ru(CO)] and 1,4-bis(2,2,2-trifluorodiazoethyl)benzene. ¹H NMR (CDCl₃, 400 MHz, p.p.m.): δ 1.85 (s, 4H), 2.61 (s, 24H), 7.26 (d, J = 6.9 Hz, 8H), 7.36 (d, J = 6.9 Hz, 8H), 7.44 (d, J = 6.9 Hz, 8H), 7.74 (d, J = 6.9 Hz, 8H), 8.22 (s, 16H). ¹⁹F NMR (CDCl₃, 470 MHz, p.p.m.): −66.09 (s). UV–vis (C₆H₆): λ_max (log ε) 401 (5.38), 533 (4.16). Unfortunately, crystallization for X-ray diffraction has not been achieved so far in spite of our efforts.#

S3. Refinement

At a late stage in the refinement, positional disorder of the C59/C60 ethyl group of the ethanol ligand and the C63 methylene group of the 1,2-dichloroethane solvent was suggested by their large U₁₁ and U₂₂ values. A disordered model over two sites was adopted, where the C atoms of the minor fragments (C592, C602 and C632) were found in a Fourier map. The displacement parameters of the major fragments (C59, C60 and C63) were refined anisotropically, and those of the minor were treated isotropically. The Cl—C and C—C bond lengths of the 1,2-dichloroethane molecules were restrained to 1.79 (2) and 1.53 (3) Å, respectively. The site-occupancy factors of the major fragments of the C59/C60 ethyl and the C63 methylene groups converged to the respective values 0.595 (18) and 0.68 (3), and those of the minor were to 0.405 (18) and 0.32 (3).

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with O—H bond lengths of 0.82, C—H bond lengths of 0.96, 0.97 and 0.93 Å for CH₃, CH₂ and aromatic CH, respectively, and with U_iso(H) values of 1.5U_eq(O or methyl C) or 1.2U_eq(methylene or aromatic C).

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 30% probability level. The 1,2-dichloromethane solvent molecules and the p-tolyl groups of the porphyrinato ligands have been omitted for clarity. All H and the C atoms of the minor fragment of the disordered ethanol ligand have also been omitted.
	Fig. 2. The unit cell packing of (I). The C and H atoms of the minor fragments of the disordered ethanol and 1,2-dichloromethane have been omitted.

µ-[1,4-phenylenebis(phenylmethylidene-κC)]bis[(ethanol-κO)(5,10,15,20- tetra-p-tolylporphyrinato-κ⁴N)ruthenium(II)] 1,2-dichloroethane trisolvate

Crystal data

[Ru2(C20H14)(C48H36N4)2(C2H6O)2]·3C2H4Cl2	Z = 1
Mr = 2183.06	F(000) = 1128
Triclinic, P1	Dx = 1.366 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 14.786 (4) Å	Cell parameters from 25 reflections
b = 15.816 (4) Å	θ = 14.9–15.0°
c = 13.879 (3) Å	µ = 0.49 mm^−1
α = 98.15 (2)°	T = 296 K
β = 109.047 (19)°	Prism, dark red
γ = 114.12 (2)°	0.50 × 0.45 × 0.18 mm
V = 2653.8 (14) Å^3

Data collection

Rigaku AFC-7R diffractometer	7914 reflections with I > 2σ(I)
Radiation source: rotating Mo anode	Rint = 0.023
Graphite monochromator	θmax = 27.5°, θmin = 2.5°
ω/2θ scans	h = 0→19
Absorption correction: ψ scan (North et al., 1968)	k = −20→18
Tmin = 0.791, Tmax = 0.917	l = −18→17
12659 measured reflections	3 standard reflections every 150 reflections
12189 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.065P)^2 + 1.3374P] where P = (Fo^2 + 2Fc^2)/3
12189 reflections	(Δ/σ)max = 0.001
663 parameters	Δρmax = 0.44 e Å^−3
7 restraints	Δρmin = −0.63 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ru	0.37171 (2)	0.23217 (2)	0.26057 (2)	0.04022 (9)
O	0.3254 (3)	0.1643 (2)	0.0729 (2)	0.0759 (9)
H44	0.2865	0.1059	0.0614	0.114*
N1	0.2730 (2)	0.2902 (2)	0.2006 (2)	0.0433 (6)
N2	0.5016 (2)	0.3492 (2)	0.2616 (2)	0.0445 (7)
N3	0.4624 (2)	0.1615 (2)	0.2880 (2)	0.0453 (7)
N4	0.2374 (2)	0.1067 (2)	0.2394 (2)	0.0416 (6)
C1	0.1628 (3)	0.2501 (3)	0.1764 (3)	0.0454 (8)
C2	0.1249 (3)	0.3149 (3)	0.1394 (3)	0.0548 (9)
H1	0.0540	0.3054	0.1186	0.066*
C3	0.2103 (3)	0.3917 (3)	0.1403 (3)	0.0528 (9)
H2	0.2089	0.4446	0.1193	0.063*
C4	0.3038 (3)	0.3777 (3)	0.1794 (3)	0.0454 (8)
C5	0.4101 (3)	0.4433 (3)	0.1955 (3)	0.0460 (8)
C6	0.5023 (3)	0.4307 (3)	0.2371 (3)	0.0462 (8)
C7	0.6114 (3)	0.5005 (3)	0.2576 (3)	0.0534 (9)
H3	0.6336	0.5617	0.2483	0.064*
C8	0.6755 (3)	0.4607 (3)	0.2930 (3)	0.0550 (10)
H4	0.7506	0.4900	0.3136	0.066*
C9	0.6072 (3)	0.3644 (3)	0.2933 (3)	0.0483 (8)
C10	0.6405 (3)	0.2954 (3)	0.3144 (3)	0.0506 (9)
C11	0.5718 (3)	0.2000 (3)	0.3081 (3)	0.0495 (9)
C12	0.6011 (3)	0.1248 (3)	0.3159 (3)	0.0564 (10)
H5	0.6699	0.1314	0.3287	0.068*
C13	0.5126 (3)	0.0429 (3)	0.3015 (3)	0.0546 (9)
H6	0.5087	−0.0171	0.3022	0.065*
C14	0.4250 (3)	0.0650 (3)	0.2850 (3)	0.0457 (8)
C15	0.3197 (3)	−0.0005 (3)	0.2713 (3)	0.0459 (8)
C16	0.2338 (3)	0.0210 (2)	0.2531 (3)	0.0445 (8)
C17	0.1264 (3)	−0.0442 (3)	0.2426 (3)	0.0538 (9)
H7	0.1035	−0.1058	0.2511	0.065*
C18	0.0659 (3)	−0.0002 (3)	0.2185 (3)	0.0530 (9)
H8	−0.0074	−0.0263	0.2056	0.064*
C19	0.1338 (3)	0.0949 (2)	0.2158 (3)	0.0447 (8)
C20	0.0989 (3)	0.1603 (3)	0.1862 (3)	0.0445 (8)
C21	0.4233 (3)	0.5322 (3)	0.1625 (3)	0.0486 (8)
C22	0.4342 (4)	0.6133 (3)	0.2282 (3)	0.0630 (11)
H9	0.4406	0.6158	0.2976	0.076*
C23	0.4357 (4)	0.6905 (3)	0.1925 (4)	0.0708 (12)
H10	0.4423	0.7438	0.2382	0.085*
C24	0.4277 (4)	0.6909 (3)	0.0916 (4)	0.0704 (12)
C25	0.4199 (5)	0.6124 (4)	0.0276 (4)	0.0831 (15)
H11	0.4169	0.6117	−0.0405	0.100*
C26	0.4165 (4)	0.5336 (3)	0.0616 (4)	0.0707 (12)
H12	0.4094	0.4804	0.0152	0.085*
C27	0.4243 (6)	0.7743 (4)	0.0521 (6)	0.114 (2)
H13	0.4080	0.7581	−0.0230	0.171*
H14	0.4941	0.8324	0.0916	0.171*
H15	0.3686	0.7856	0.0627	0.171*
C28	0.7580 (3)	0.3231 (3)	0.3404 (3)	0.0522 (9)
C29	0.8267 (4)	0.3299 (4)	0.4393 (4)	0.0820 (15)
H16	0.8006	0.3180	0.4912	0.098*
C30	0.9346 (4)	0.3542 (4)	0.4626 (4)	0.0884 (16)
H17	0.9794	0.3592	0.5306	0.106*
C31	0.9770 (3)	0.3710 (3)	0.3897 (4)	0.0679 (12)
C32	0.9081 (4)	0.3626 (4)	0.2906 (4)	0.0761 (13)
H18	0.9342	0.3730	0.2384	0.091*
C33	0.7996 (3)	0.3387 (4)	0.2660 (4)	0.0666 (11)
H19	0.7548	0.3333	0.1977	0.080*
C34	1.0950 (4)	0.3960 (4)	0.4161 (5)	0.0916 (17)
H20	1.0981	0.3618	0.3554	0.137*
H21	1.1224	0.3769	0.4771	0.137*
H22	1.1389	0.4651	0.4325	0.137*
C35	0.2969 (3)	−0.1000 (3)	0.2789 (3)	0.0505 (9)
C36	0.3409 (4)	−0.1142 (3)	0.3762 (3)	0.0660 (11)
H23	0.3889	−0.0603	0.4379	0.079*
C37	0.3147 (4)	−0.2072 (4)	0.3832 (4)	0.0742 (13)
H24	0.3447	−0.2141	0.4498	0.089*
C38	0.2464 (4)	−0.2884 (3)	0.2958 (4)	0.0635 (11)
C39	0.2045 (5)	−0.2746 (3)	0.1998 (4)	0.0808 (15)
H25	0.1582	−0.3289	0.1382	0.097*
C40	0.2284 (4)	−0.1834 (3)	0.1909 (4)	0.0767 (14)
H26	0.1974	−0.1777	0.1238	0.092*
C41	0.2173 (5)	−0.3883 (4)	0.3037 (5)	0.0914 (17)
H27	0.2081	−0.4294	0.2395	0.137*
H28	0.1501	−0.4149	0.3120	0.137*
H29	0.2747	−0.3848	0.3648	0.137*
C42	−0.0192 (3)	0.1305 (3)	0.1572 (3)	0.0454 (8)
C43	−0.0561 (3)	0.1354 (3)	0.2361 (3)	0.0626 (11)
H30	−0.0074	0.1571	0.3080	0.075*
C44	−0.1655 (3)	0.1082 (4)	0.2089 (4)	0.0710 (13)
H31	−0.1890	0.1116	0.2632	0.085*
C45	−0.2396 (3)	0.0767 (3)	0.1040 (4)	0.0575 (10)
C46	−0.2028 (3)	0.0708 (3)	0.0262 (3)	0.0626 (11)
H32	−0.2519	0.0489	−0.0456	0.075*
C47	−0.0939 (3)	0.0968 (3)	0.0517 (3)	0.0613 (11)
H33	−0.0715	0.0913	−0.0030	0.074*
C48	−0.3591 (4)	0.0461 (4)	0.0723 (5)	0.0854 (15)
H34	−0.4014	0.0048	−0.0013	0.128*
H35	−0.3681	0.1031	0.0803	0.128*
H36	−0.3839	0.0111	0.1177	0.128*
C49	0.3980 (3)	0.2902 (2)	0.4006 (3)	0.0417 (7)
C50	0.3632 (3)	0.2359 (3)	0.4741 (3)	0.0496 (9)
C51	0.3071 (4)	0.2599 (4)	0.5265 (4)	0.0731 (13)
H37	0.2912	0.3100	0.5159	0.088*
C52	0.2742 (5)	0.2108 (4)	0.5944 (5)	0.0921 (17)
H38	0.2365	0.2280	0.6285	0.111*
C53	0.2968 (5)	0.1381 (4)	0.6111 (4)	0.0889 (16)
H39	0.2737	0.1047	0.6558	0.107*
C54	0.3534 (5)	0.1134 (4)	0.5626 (4)	0.0808 (15)
H40	0.3699	0.0642	0.5753	0.097*
C55	0.3862 (4)	0.1622 (3)	0.4942 (3)	0.0653 (11)
H41	0.4244	0.1447	0.4613	0.078*
C56	0.4490 (3)	0.3979 (2)	0.4486 (3)	0.0391 (7)
C57	0.5616 (3)	0.4532 (2)	0.5114 (3)	0.0426 (7)
H42	0.6043	0.4226	0.5196	0.051*
C58	0.6113 (3)	0.5528 (2)	0.5619 (3)	0.0442 (8)
H43	0.6865	0.5875	0.6036	0.053*
C59	0.2715 (16)	0.1956 (11)	−0.0144 (8)	0.123 (6)	0.595 (18)
H45	0.1957	0.1708	−0.0259	0.148*	0.595 (18)
H46	0.3064	0.2664	0.0104	0.148*	0.595 (18)
C60	0.2733 (9)	0.1656 (8)	−0.1161 (8)	0.091 (4)	0.595 (18)
H47	0.1997	0.1299	−0.1714	0.137*	0.595 (18)
H48	0.3066	0.1245	−0.1128	0.137*	0.595 (18)
H49	0.3147	0.2222	−0.1320	0.137*	0.595 (18)
C592	0.3454 (14)	0.2072 (11)	0.0035 (12)	0.080 (5)*	0.405 (18)
H452	0.3782	0.1786	−0.0311	0.096*	0.405 (18)
H462	0.3986	0.2757	0.0416	0.096*	0.405 (18)
C602	0.249 (2)	0.201 (2)	−0.079 (2)	0.156 (11)*	0.405 (18)
H472	0.1909	0.1815	−0.0571	0.233*	0.405 (18)
H482	0.2270	0.1527	−0.1454	0.233*	0.405 (18)
H492	0.2672	0.2630	−0.0900	0.233*	0.405 (18)
Cl1	0.9036 (2)	0.4837 (2)	0.0630 (2)	0.1709 (10)
C61	0.8984 (10)	0.5568 (8)	0.1652 (9)	0.184 (4)
H50	0.8342	0.5169	0.1754	0.221*
H51	0.9619	0.5760	0.2313	0.221*
C62	0.8951 (12)	0.6342 (9)	0.1526 (9)	0.217 (6)
H52	0.8318	0.6161	0.0868	0.326*
H53	0.9599	0.6756	0.1442	0.326*
Cl2	0.8884 (3)	0.7013 (2)	0.2595 (2)	0.1868 (11)
Cl3	0.9486 (3)	0.1086 (3)	0.4997 (3)	0.2232 (16)
C63	0.9871 (10)	0.0235 (9)	0.5435 (8)	0.155 (9)	0.68 (3)
H54	1.0512	0.0563	0.6120	0.186*	0.68 (3)
H55	0.9280	−0.0265	0.5526	0.186*	0.68 (3)
C632	0.978 (3)	0.017 (2)	0.4506 (17)	0.158 (16)*	0.32 (3)
H542	0.9130	−0.0374	0.3925	0.190*	0.32 (3)
H552	1.0337	0.0438	0.4241	0.190*	0.32 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru	0.03545 (14)	0.03897 (14)	0.04303 (15)	0.01716 (11)	0.01711 (11)	0.00622 (11)
O	0.088 (2)	0.0639 (19)	0.0591 (18)	0.0309 (17)	0.0262 (17)	0.0054 (15)
N1	0.0368 (15)	0.0436 (16)	0.0457 (16)	0.0178 (13)	0.0173 (13)	0.0101 (13)
N2	0.0380 (15)	0.0460 (16)	0.0471 (16)	0.0198 (13)	0.0195 (13)	0.0073 (13)
N3	0.0389 (15)	0.0444 (16)	0.0511 (17)	0.0201 (13)	0.0205 (13)	0.0087 (13)
N4	0.0368 (14)	0.0404 (15)	0.0425 (15)	0.0176 (12)	0.0154 (12)	0.0061 (12)
C1	0.0366 (17)	0.0482 (19)	0.048 (2)	0.0207 (16)	0.0162 (15)	0.0094 (16)
C2	0.0414 (19)	0.057 (2)	0.064 (2)	0.0256 (18)	0.0187 (18)	0.0168 (19)
C3	0.048 (2)	0.053 (2)	0.059 (2)	0.0274 (18)	0.0206 (18)	0.0209 (18)
C4	0.0447 (19)	0.0444 (19)	0.0459 (19)	0.0214 (16)	0.0189 (16)	0.0131 (15)
C5	0.0463 (19)	0.0426 (18)	0.046 (2)	0.0192 (16)	0.0207 (16)	0.0116 (15)
C6	0.0423 (19)	0.0466 (19)	0.047 (2)	0.0189 (16)	0.0213 (16)	0.0094 (16)
C7	0.047 (2)	0.049 (2)	0.062 (2)	0.0187 (17)	0.0276 (19)	0.0163 (18)
C8	0.041 (2)	0.055 (2)	0.063 (2)	0.0163 (18)	0.0269 (18)	0.0119 (19)
C9	0.0377 (18)	0.053 (2)	0.050 (2)	0.0177 (16)	0.0220 (16)	0.0091 (17)
C10	0.0400 (19)	0.060 (2)	0.052 (2)	0.0245 (18)	0.0228 (17)	0.0088 (18)
C11	0.0436 (19)	0.054 (2)	0.051 (2)	0.0255 (17)	0.0213 (17)	0.0086 (17)
C12	0.049 (2)	0.067 (3)	0.063 (2)	0.036 (2)	0.0257 (19)	0.019 (2)
C13	0.057 (2)	0.056 (2)	0.064 (2)	0.037 (2)	0.030 (2)	0.0196 (19)
C14	0.048 (2)	0.048 (2)	0.0429 (19)	0.0265 (17)	0.0200 (16)	0.0100 (15)
C15	0.051 (2)	0.0428 (18)	0.0440 (19)	0.0233 (16)	0.0210 (16)	0.0098 (15)
C16	0.0459 (19)	0.0421 (18)	0.0441 (19)	0.0199 (16)	0.0206 (16)	0.0115 (15)
C17	0.049 (2)	0.043 (2)	0.066 (2)	0.0170 (17)	0.0277 (19)	0.0174 (18)
C18	0.042 (2)	0.048 (2)	0.067 (2)	0.0187 (17)	0.0254 (18)	0.0195 (18)
C19	0.0353 (17)	0.0435 (19)	0.0457 (19)	0.0150 (15)	0.0149 (15)	0.0070 (15)
C20	0.0339 (17)	0.0482 (19)	0.0451 (19)	0.0176 (15)	0.0155 (15)	0.0082 (15)
C21	0.0423 (19)	0.050 (2)	0.052 (2)	0.0202 (16)	0.0197 (16)	0.0187 (17)
C22	0.074 (3)	0.055 (2)	0.052 (2)	0.029 (2)	0.021 (2)	0.0148 (19)
C23	0.070 (3)	0.051 (2)	0.077 (3)	0.028 (2)	0.020 (2)	0.016 (2)
C24	0.064 (3)	0.060 (3)	0.079 (3)	0.023 (2)	0.025 (2)	0.031 (2)
C25	0.105 (4)	0.084 (3)	0.073 (3)	0.042 (3)	0.049 (3)	0.045 (3)
C26	0.094 (3)	0.062 (3)	0.066 (3)	0.035 (3)	0.048 (3)	0.027 (2)
C27	0.122 (5)	0.084 (4)	0.135 (6)	0.050 (4)	0.041 (4)	0.065 (4)
C28	0.0377 (19)	0.057 (2)	0.064 (2)	0.0230 (17)	0.0252 (18)	0.0144 (19)
C29	0.052 (3)	0.127 (4)	0.065 (3)	0.041 (3)	0.028 (2)	0.026 (3)
C30	0.047 (3)	0.134 (5)	0.069 (3)	0.041 (3)	0.015 (2)	0.026 (3)
C31	0.041 (2)	0.070 (3)	0.086 (3)	0.025 (2)	0.026 (2)	0.018 (2)
C32	0.059 (3)	0.100 (4)	0.088 (3)	0.043 (3)	0.046 (3)	0.033 (3)
C33	0.053 (2)	0.093 (3)	0.067 (3)	0.039 (2)	0.032 (2)	0.031 (2)
C34	0.044 (2)	0.104 (4)	0.119 (5)	0.034 (3)	0.032 (3)	0.026 (3)
C35	0.052 (2)	0.049 (2)	0.052 (2)	0.0264 (18)	0.0243 (18)	0.0136 (17)
C36	0.072 (3)	0.054 (2)	0.056 (2)	0.022 (2)	0.022 (2)	0.015 (2)
C37	0.093 (4)	0.078 (3)	0.069 (3)	0.044 (3)	0.043 (3)	0.040 (3)
C38	0.075 (3)	0.054 (2)	0.078 (3)	0.038 (2)	0.039 (2)	0.027 (2)
C39	0.117 (4)	0.049 (2)	0.073 (3)	0.044 (3)	0.034 (3)	0.014 (2)
C40	0.106 (4)	0.061 (3)	0.054 (3)	0.043 (3)	0.022 (3)	0.013 (2)
C41	0.114 (4)	0.072 (3)	0.118 (5)	0.057 (3)	0.060 (4)	0.045 (3)
C42	0.0359 (17)	0.0433 (18)	0.050 (2)	0.0169 (15)	0.0161 (16)	0.0090 (16)
C43	0.042 (2)	0.082 (3)	0.049 (2)	0.026 (2)	0.0150 (18)	0.006 (2)
C44	0.050 (2)	0.090 (3)	0.071 (3)	0.032 (2)	0.031 (2)	0.011 (2)
C45	0.0379 (19)	0.057 (2)	0.075 (3)	0.0208 (18)	0.022 (2)	0.024 (2)
C46	0.045 (2)	0.068 (3)	0.053 (2)	0.018 (2)	0.0076 (19)	0.019 (2)
C47	0.047 (2)	0.075 (3)	0.052 (2)	0.022 (2)	0.0209 (19)	0.017 (2)
C48	0.048 (2)	0.093 (4)	0.113 (4)	0.034 (3)	0.032 (3)	0.034 (3)
C49	0.0364 (17)	0.0407 (17)	0.0435 (18)	0.0197 (14)	0.0140 (15)	0.0056 (14)
C50	0.049 (2)	0.0442 (19)	0.0414 (19)	0.0177 (16)	0.0126 (16)	0.0057 (15)
C51	0.081 (3)	0.075 (3)	0.091 (3)	0.042 (3)	0.059 (3)	0.038 (3)
C52	0.105 (4)	0.093 (4)	0.109 (4)	0.045 (3)	0.078 (4)	0.046 (3)
C53	0.116 (5)	0.072 (3)	0.077 (3)	0.032 (3)	0.054 (3)	0.030 (3)
C54	0.121 (4)	0.072 (3)	0.058 (3)	0.051 (3)	0.038 (3)	0.031 (2)
C55	0.090 (3)	0.066 (3)	0.048 (2)	0.045 (3)	0.029 (2)	0.018 (2)
C56	0.0371 (16)	0.0400 (17)	0.0378 (17)	0.0180 (14)	0.0157 (14)	0.0094 (14)
C57	0.0404 (17)	0.0464 (18)	0.0427 (18)	0.0263 (15)	0.0153 (15)	0.0088 (15)
C58	0.0322 (16)	0.0467 (19)	0.0425 (18)	0.0183 (15)	0.0086 (14)	0.0042 (15)
C59	0.189 (16)	0.184 (13)	0.060 (6)	0.147 (12)	0.052 (8)	0.038 (7)
C60	0.116 (8)	0.099 (7)	0.063 (6)	0.056 (6)	0.038 (5)	0.028 (5)
Cl1	0.212 (3)	0.187 (2)	0.1279 (17)	0.111 (2)	0.0773 (18)	0.0326 (16)
C61	0.216 (11)	0.172 (10)	0.219 (12)	0.108 (9)	0.131 (10)	0.079 (9)
C62	0.314 (17)	0.201 (12)	0.204 (12)	0.165 (13)	0.125 (12)	0.089 (10)
Cl2	0.224 (3)	0.174 (2)	0.189 (3)	0.108 (2)	0.111 (2)	0.042 (2)
Cl3	0.236 (4)	0.199 (3)	0.145 (2)	0.032 (3)	0.079 (2)	0.048 (2)
C63	0.126 (11)	0.193 (17)	0.074 (7)	0.010 (10)	0.044 (7)	0.050 (8)

Geometric parameters (Å, º)

Ru—N1	2.046 (3)	C34—H22	0.9600
Ru—N2	2.046 (3)	C35—C40	1.379 (6)
Ru—N3	2.051 (3)	C35—C36	1.389 (6)
Ru—N4	2.050 (3)	C36—C37	1.386 (6)
Ru—C49	1.865 (3)	C36—H23	0.9300
Ru—O	2.417 (3)	C37—C38	1.356 (6)
O—C59	1.487 (12)	C37—H24	0.9300
O—C592	1.298 (14)	C38—C39	1.365 (6)
O—H44	0.8200	C38—C41	1.488 (6)
N1—C1	1.380 (4)	C39—C40	1.372 (6)
N1—C4	1.377 (4)	C39—H25	0.9300
N2—C6	1.376 (5)	C40—H26	0.9300
N2—C9	1.379 (4)	C41—H27	0.9600
N3—C11	1.384 (4)	C41—H28	0.9600
N3—C14	1.382 (4)	C41—H29	0.9600
N4—C16	1.378 (4)	C42—C47	1.374 (5)
N4—C19	1.382 (4)	C42—C43	1.380 (5)
C1—C20	1.404 (5)	C43—C44	1.391 (5)
C1—C2	1.436 (5)	C43—H30	0.9300
C2—C3	1.343 (5)	C44—C45	1.369 (6)
C2—H1	0.9300	C44—H31	0.9300
C3—C4	1.431 (5)	C45—C46	1.365 (6)
C3—H2	0.9300	C45—C48	1.512 (5)
C4—C5	1.403 (5)	C46—C47	1.390 (6)
C5—C6	1.404 (5)	C46—H32	0.9300
C5—C21	1.496 (5)	C47—H33	0.9300
C6—C7	1.435 (5)	C48—H34	0.9600
C7—C8	1.344 (5)	C48—H35	0.9600
C7—H3	0.9300	C48—H36	0.9600
C8—C9	1.444 (5)	C49—C50	1.507 (5)
C8—H4	0.9300	C49—C56	1.489 (4)
C9—C10	1.399 (5)	C50—C55	1.382 (5)
C10—C11	1.404 (5)	C50—C51	1.391 (6)
C10—C28	1.504 (5)	C51—C52	1.387 (6)
C11—C12	1.429 (5)	C51—H37	0.9300
C12—C13	1.342 (5)	C52—C53	1.353 (7)
C12—H5	0.9300	C52—H38	0.9300
C13—C14	1.432 (5)	C53—C54	1.365 (7)
C13—H6	0.9300	C53—H39	0.9300
C14—C15	1.402 (5)	C54—C55	1.391 (6)
C15—C16	1.400 (5)	C54—H40	0.9300
C15—C35	1.496 (5)	C55—H41	0.9300
C16—C17	1.440 (5)	C56—C58^i	1.393 (5)
C17—C18	1.333 (5)	C56—C57	1.394 (5)
C17—H7	0.9300	C57—C58	1.384 (5)
C18—C19	1.442 (5)	C57—H42	0.9300
C18—H8	0.9300	C58—C56^i	1.393 (5)
C19—C20	1.386 (5)	C58—H43	0.9300
C20—C42	1.499 (5)	C59—C60	1.436 (17)
C21—C26	1.374 (5)	C59—H45	0.9700
C21—C22	1.382 (5)	C59—H46	0.9700
C22—C23	1.375 (6)	C60—H47	0.9600
C22—H9	0.9300	C60—H48	0.9600
C23—C24	1.367 (7)	C60—H49	0.9600
C23—H10	0.9300	C592—C602	1.46 (3)
C24—C25	1.360 (7)	C592—H452	0.9700
C24—C27	1.512 (6)	C592—H462	0.9700
C25—C26	1.382 (6)	C602—H472	0.9600
C25—H11	0.9300	C602—H482	0.9600
C26—H12	0.9300	C602—H492	0.9600
C27—H13	0.9600	Cl1—C61	1.743 (9)
C27—H14	0.9600	C61—C62	1.279 (10)
C27—H15	0.9600	C61—H50	0.9700
C28—C33	1.368 (6)	C61—H51	0.9700
C28—C29	1.374 (6)	C62—Cl2	1.753 (10)
C29—C30	1.386 (6)	C62—H52	0.9700
C29—H16	0.9300	C62—H53	0.9700
C30—C31	1.357 (7)	Cl3—C63	1.771 (14)
C30—H17	0.9300	Cl3—C632	1.785 (18)
C31—C32	1.368 (7)	C63—C63^ii	1.56 (2)
C31—C34	1.520 (6)	C63—H54	0.9700
C32—C33	1.393 (6)	C63—H55	0.9700
C32—H18	0.9300	C632—C632^ii	1.58 (3)
C33—H19	0.9300	C632—H542	0.9700
C34—H20	0.9600	C632—H552	0.9700
C34—H21	0.9600
C23···C54^i	3.617 (7)	C46···C15^iii	3.707 (6)
H10···C54^i	3.011	H32···C15^iii	2.836
C55···C14	3.416 (6)	Cl2···Cl3^iv	3.462 (5)
H41···C14	2.593
N1—Ru—N2	89.84 (11)	C32—C33—H19	119.4
N1—Ru—N3	168.18 (11)	C31—C34—H20	109.5
N1—Ru—N4	89.90 (11)	C31—C34—H21	109.5
N2—Ru—N3	89.56 (12)	H20—C34—H21	109.5
N2—Ru—N4	172.57 (11)	C31—C34—H22	109.5
N3—Ru—N4	89.18 (11)	H20—C34—H22	109.5
N1—Ru—O	83.22 (11)	H21—C34—H22	109.5
N2—Ru—O	86.05 (12)	C15—C35—C36	121.8 (3)
N3—Ru—O	84.96 (12)	C15—C35—C40	122.3 (4)
N4—Ru—O	86.54 (12)	C36—C35—C40	115.8 (4)
C49—Ru—N1	90.83 (13)	C35—C36—C37	121.3 (4)
C49—Ru—N2	94.10 (13)	C37—C36—H23	119.4
C49—Ru—N3	100.99 (13)	C35—C36—H23	119.4
C49—Ru—N4	93.32 (13)	C36—C37—C38	122.0 (4)
C49—Ru—O	174.05 (13)	C38—C37—H24	119.0
Ru—O—C59	124.0 (5)	C36—C37—H24	119.0
C59—O—H44	109.5	C37—C38—C39	116.8 (4)
Ru—O—C592	130.5 (7)	C37—C38—C41	121.9 (5)
C592—O—H44	127.5	C39—C38—C41	121.2 (5)
Ru—O—H44	101.7	C38—C39—C40	122.3 (4)
C1—N1—C4	106.8 (3)	C38—C39—H25	118.9
Ru—N1—C1	126.3 (2)	C40—C39—H25	118.9
Ru—N1—C4	126.9 (2)	C35—C40—C39	121.8 (4)
C6—N2—C9	106.7 (3)	C39—C40—H26	119.1
Ru—N2—C6	126.6 (2)	C35—C40—H26	119.1
Ru—N2—C9	126.6 (3)	C38—C41—H27	109.5
Ru—N3—C11	126.5 (2)	C38—C41—H28	109.5
Ru—N3—C14	126.7 (2)	H27—C41—H28	109.5
C11—N3—C14	106.8 (3)	C38—C41—H29	109.5
Ru—N4—C16	127.3 (2)	H27—C41—H29	109.5
Ru—N4—C19	125.7 (2)	H28—C41—H29	109.5
C16—N4—C19	106.8 (3)	C20—C42—C43	120.6 (3)
N1—C1—C2	108.8 (3)	C20—C42—C47	121.3 (3)
N1—C1—C20	125.3 (3)	C43—C42—C47	118.0 (3)
C2—C1—C20	125.9 (3)	C42—C43—C44	120.5 (4)
C4—C5—C21	116.0 (3)	C42—C43—H30	119.7
C6—C5—C21	118.6 (3)	C44—C43—H30	119.7
N2—C6—C5	125.6 (3)	C43—C44—C45	121.5 (4)
N2—C6—C7	109.7 (3)	C45—C44—H31	119.3
C5—C6—C7	124.7 (3)	C43—C44—H31	119.3
C6—C7—C8	107.0 (3)	C44—C45—C46	117.7 (4)
C8—C7—H3	126.5	C46—C45—C48	119.8 (4)
C6—C7—H3	126.5	C44—C45—C48	122.5 (4)
C7—C8—C9	108.0 (3)	C45—C46—C47	121.7 (4)
C7—C8—H4	126.0	C45—C46—H32	119.2
C9—C8—H4	126.0	C47—C46—H32	119.2
N2—C9—C10	125.5 (3)	C42—C47—C46	120.6 (4)
N2—C9—C8	108.5 (3)	C42—C47—H33	119.7
C8—C9—C10	125.8 (3)	C46—C47—H33	119.7
C9—C10—C11	125.2 (3)	C45—C48—H34	109.5
C9—C10—C28	117.9 (3)	C45—C48—H35	109.5
C11—C10—C28	116.8 (3)	H34—C48—H35	109.5
N3—C11—C10	125.6 (3)	C45—C48—H36	109.5
N3—C11—C12	108.5 (3)	H34—C48—H36	109.5
C10—C11—C12	125.9 (3)	H35—C48—H36	109.5
C11—C12—C13	108.3 (3)	C50—C49—C56	112.3 (3)
C11—C12—H5	125.8	Ru—C49—C56	122.2 (3)
C13—C12—H5	125.8	Ru—C49—C50	125.3 (2)
C12—C13—C14	107.4 (3)	C51—C50—C55	116.9 (4)
C12—C13—H6	126.3	C49—C50—C55	122.5 (4)
C14—C13—H6	126.3	C49—C50—C51	120.6 (4)
N3—C14—C13	109.0 (3)	C50—C51—C52	121.5 (5)
C1—C2—C3	107.6 (3)	C52—C51—H37	119.3
C3—C2—H1	126.2	C50—C51—H37	119.3
C1—C2—H1	126.2	C51—C52—C53	120.0 (5)
C2—C3—C4	107.8 (3)	C53—C52—H38	120.0
C2—C3—H2	126.1	C51—C52—H38	120.0
C4—C3—H2	126.1	C52—C53—C54	120.3 (5)
N1—C4—C5	125.4 (3)	C52—C53—H39	119.8
N1—C4—C3	109.0 (3)	C54—C53—H39	119.8
C3—C4—C5	125.6 (3)	C53—C54—C55	119.8 (5)
C4—C5—C6	125.3 (3)	C53—C54—H40	120.1
N3—C14—C15	126.1 (3)	C55—C54—H40	120.1
C13—C14—C15	124.9 (3)	C50—C55—C54	121.4 (4)
C14—C15—C16	124.7 (3)	C50—C55—H41	119.3
C14—C15—C35	118.4 (3)	C54—C55—H41	119.3
C16—C15—C35	116.9 (3)	C58^i—C56—C57	117.2 (3)
N4—C16—C15	125.5 (3)	C58^i—C56—C49	123.1 (3)
N4—C16—C17	109.1 (3)	C49—C56—C57	119.7 (3)
C15—C16—C17	125.4 (3)	C56—C57—C58	121.4 (3)
C16—C17—C18	107.4 (3)	C58—C57—H42	119.3
C18—C17—H7	126.3	C56—C57—H42	119.3
C16—C17—H7	126.3	C57—C58—C56^i	121.4 (3)
C17—C18—C19	108.2 (3)	C57—C58—H43	119.3
C17—C18—H8	125.9	C56^i—C58—H43	119.3
C19—C18—H8	125.9	O—C59—C60	116.6 (12)
N4—C19—C20	125.7 (3)	C60—C59—H45	108.2
N4—C19—C18	108.4 (3)	O—C59—H45	108.2
C18—C19—C20	125.7 (3)	C60—C59—H46	108.2
C1—C20—C19	125.9 (3)	O—C59—H46	108.2
C19—C20—C42	117.2 (3)	H45—C59—H46	107.3
C1—C20—C42	116.8 (3)	C59—C60—H47	109.5
C22—C21—C26	116.8 (4)	C59—C60—H48	109.5
C5—C21—C26	121.2 (4)	H47—C60—H48	109.5
C5—C21—C22	121.8 (3)	C59—C60—H49	109.5
C21—C22—C23	120.9 (4)	H47—C60—H49	109.5
C23—C22—H9	119.5	H48—C60—H49	109.5
C21—C22—H9	119.5	O—C592—C602	114.5 (18)
C22—C23—C24	121.9 (5)	O—C592—H452	108.6
C24—C23—H10	119.1	C602—C592—H452	108.6
C22—C23—H10	119.1	O—C592—H462	108.6
C23—C24—C25	117.4 (4)	C602—C592—H462	108.6
C25—C24—C27	121.5 (5)	H452—C592—H462	107.6
C23—C24—C27	121.1 (5)	C592—C602—H472	109.5
C24—C25—C26	121.4 (5)	C592—C602—H482	109.5
C24—C25—H11	119.3	H472—C602—H482	109.5
C26—C25—H11	119.3	C592—C602—H492	109.5
C21—C26—C25	121.5 (4)	H472—C602—H492	109.5
C21—C26—H12	119.2	H482—C602—H492	109.5
C25—C26—H12	119.2	C62—C61—Cl1	117.6 (9)
C24—C27—H13	109.5	C62—C61—H50	107.9
C24—C27—H14	109.5	Cl1—C61—H50	107.9
H13—C27—H14	109.5	C62—C61—H51	107.9
C24—C27—H15	109.5	Cl1—C61—H51	107.9
H13—C27—H15	109.5	H50—C61—H51	107.2
H14—C27—H15	109.5	C61—C62—Cl2	113.7 (9)
C29—C28—C33	117.2 (4)	C61—C62—H52	108.8
C10—C28—C29	120.9 (4)	Cl2—C62—H52	108.8
C10—C28—C33	121.8 (4)	C61—C62—H53	108.8
C28—C29—C30	120.8 (4)	Cl2—C62—H53	108.8
C28—C29—H16	119.6	H52—C62—H53	107.7
C30—C29—H16	119.6	C63^ii—C63—Cl3	107.9 (10)
C29—C30—C31	122.4 (5)	C63^ii—C63—H54	110.1
C31—C30—H17	118.8	Cl3—C63—H54	110.1
C29—C30—H17	118.8	C63^ii—C63—H55	110.1
C30—C31—C32	116.9 (4)	Cl3—C63—H55	110.1
C30—C31—C34	121.6 (5)	H54—C63—H55	108.4
C32—C31—C34	121.5 (5)	C632^ii—C632—Cl3	106.0 (18)
C31—C32—C33	121.5 (4)	C632^ii—C632—H542	110.5
C31—C32—H18	119.2	Cl3—C632—H542	110.5
C33—C32—H18	119.2	C632^ii—C632—H552	110.5
C28—C33—C32	121.2 (4)	Cl3—C632—H552	110.5
C28—C33—H19	119.4	H542—C632—H552	108.7
N1—Ru—O—C59	12.9 (10)	Ru—C49—C56—C58^i	87.8 (4)
N2—Ru—O—C59	−77.4 (10)	C50—C49—C56—C57	89.5 (4)
N3—Ru—O—C59	−167.3 (10)	C50—C49—C56—C58^i	−87.5 (4)
N4—Ru—O—C59	103.2 (10)	C4—C5—C21—C22	82.0 (5)
C49—Ru—O—C59	14.3 (17)	C6—C5—C21—C22	−99.5 (4)
N1—Ru—O—C592	63.0 (12)	C4—C5—C21—C26	−92.8 (5)
N2—Ru—O—C592	−27.3 (12)	C6—C5—C21—C26	85.7 (5)
N3—Ru—O—C592	−117.2 (12)	C9—C10—C28—C29	116.3 (5)
N4—Ru—O—C592	153.3 (12)	C11—C10—C28—C29	−66.7 (5)
C49—Ru—O—C592	64.4 (18)	C9—C10—C28—C33	−66.3 (5)
N1—Ru—C49—C50	115.0 (3)	C11—C10—C28—C33	110.6 (5)
N2—Ru—C49—C50	−155.1 (3)	C16—C15—C35—C36	−107.6 (4)
N3—Ru—C49—C50	−64.7 (3)	C14—C15—C35—C36	71.1 (5)
N4—Ru—C49—C50	25.1 (3)	C16—C15—C35—C40	70.1 (5)
O—Ru—C49—C50	113.6 (12)	C14—C15—C35—C40	−111.2 (5)
N1—Ru—C49—C56	−59.6 (3)	C1—C20—C42—C43	−105.8 (4)
N2—Ru—C49—C56	30.3 (3)	C19—C20—C42—C43	77.0 (5)
N3—Ru—C49—C56	120.6 (3)	C1—C20—C42—C47	74.9 (5)
N4—Ru—C49—C56	−149.6 (3)	C19—C20—C42—C47	−102.4 (4)
O—Ru—C49—C56	−61.0 (14)	C592—O—C59—C60	51.1 (13)
Ru—C49—C50—C51	−129.6 (4)	Ru—O—C59—C60	165.6 (9)
Ru—C49—C50—C55	51.5 (5)	C59—O—C592—C602	−12.1 (19)
C56—C49—C50—C51	45.5 (5)	Ru—O—C592—C602	−109.2 (18)
C56—C49—C50—C55	−133.4 (4)	Cl1—C61—C62—Cl2	179.3 (6)
Ru—C49—C56—C57	−95.2 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z+1; (iii) −x, −y, −z; (iv) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O—H44···C46^iii	0.82	2.46	3.227 (5)	156

Symmetry code: (iii) −x, −y, −z.