Bis(μ-η²-benzene-1,2-di­thiol­ato-κ³S,S′:S′)bis­[(η⁶-p-cymene)­ruthenium(II)]

In solution, the complex [Ru(bdt)(cym)] and its dimer [Ru₂(bdt)₂(cym)₂] [bdt is benzene-1,2-di­thiol­ate (C₆H₄S₂) and cym is p-cymene (C₁₀H₁₄)] are in equilibrium in a ratio which depends on temperature (ca 1:1 at 298 K). In the solid state and in solution at low temperature (213 K), only the dimer is observed. In the crystal structure of [Ru₂(bdt)₂(cym)₂], each Ru atom is bonded to three S atoms from two bdt ligands apart from its coordination to the benzene ring of the p-cymene ligand.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.041
• wR factor = 0.105
• Data-to-parameter ratio = 16.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

This work is part of a project dealing with the synthesis and reactivity of binuclear complexes containing bridging benzene-1,2-dithiolate ligands (Cabeza et al., 1998, 1999). The nuclearity of the [Ru(bdt)(arene)]_x compounds (bdt is benzene-1,2-dithiolate) is strongly dependent on temperature and the nature of the substituents of the arene ring, i.e. [Ru(bdt)(C₆Me₆)] is a monomer in the solid state and in solution at any temperature, while [Ru(bdt)(C₆H₆)] and [Ru(bdt)(cym)] exist in solution in equilibrium with their dimers (Mashima et al., 1997). With the aim of studying its reactivity with other metal complexes, [Ru(bdt)(cym)]_x (cym is p-cymene) was prepared and it was observed that, first, in solution, at 298 K, a ca 1:1 equilibrium mixture of the monomer and the dimer exists (see Scheme below), secondly, in solution, but at temperatures above 298 K, the monomer predominates (a 4:1 ratio was observed at 353 K), while at lower temperatures, the dimer is in higher ratio, e.g. at 213 K, only the dimer was noticed, and thirdly, only the dimer exists in the solid state. We report here the structural details of the dimer [Ru₂(bdt)₂(cym)₂], (I).

The dimer crystallizes in P1. The asymmetric unit consists of one-half of the dimer, i.e. a monomeric unit, [Ru(bdt)(cym)], with the other half being generated by a centre of symmetry at (0,1/2,1/2). The monomeric units are linked through two Ru—S bonds, Ru1—S1ⁱ [2.364 (2) Å; symmetry code: -x, 1 - y, 1 - z] and Ru1—S2ⁱ [2.386 (2) Å], i.e. each Ru atom is bonded to three S atoms (S1, S1ⁱ and S2ⁱ) from two bdt ligands apart from its coordination to the benzene ring of the p-cymene ligand.

Although other related compounds, such as [Ru₂(bdt)₂(C₅Me₅)₂] (Ru–Ru) (Hörnig et al., 1994) and [Rh₂(bdt)₂(C₅Me₅)₂] (Russell et al., 1978), are known, structure details have not been reported.

S2. Experimental

The title compound was prepared by the method reported in Mashima et al. (1997). The monomer to dimer ratios in solution at different temperatures were estimated by integration of ¹H NMR spectra in toluene-d₈. The ¹H NMR chemical shifts of monomer and dimer have been reported (Mashima et al., 1997). Crystals were obtained at 253 K by slow diffusion of pentane vapour into a solution of the complex in dichloromethane.

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CRYSDA (Beurskens et al., 1992); data reduction: REFLEX (García-Granda et al., 1999); program(s) used to solve structure: DIRDIF (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: EUCLID (Spek, 1982); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. View of [Ru2(bdt)2(cym)2]. Displacement ellipsoids are shown at the 30% probability level. H atoms have been omitted for clarity.

Bis(µ-η²-benzene-1,2-dithiolato-κ³S,S':S')bis[(η⁶-p- cymene)ruthenium(II)]

Crystal data

[Ru2(C10H14)2(C6H4S2)2]	Z = 1
Mr = 750.98	F(000) = 380
Triclinic, P1	Dx = 1.706 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.237 (5) Å	Cell parameters from 25 reflections
b = 9.813 (6) Å	θ = 10–15°
c = 10.237 (3) Å	µ = 1.34 mm^−1
α = 65.42 (4)°	T = 293 K
β = 82.57 (3)°	Plate, dark red
γ = 76.34 (6)°	0.33 × 0.17 × 0.03 mm
V = 730.8 (7) Å^3

Data collection

Nonius CAD-4 diffractometer	1907 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 26.0°, θmin = 2.2°
ω–2θ scans	h = −10→10
Absorption correction: part of the refinement model (ΔF) (SHELXA; Sheldrick, 1997)	k = −10→12
Tmin = 0.762, Tmax = 0.957	l = 0→12
3022 measured reflections	3 standard reflections every 200 reflections
2855 independent reflections	intensity decay: 3.6%

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0492P)^2] where P = (Fo^2 + 2Fc^2)/3
2855 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.85 e Å^−3
0 restraints	Δρmin = −0.69 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
Ru1	0.08675 (7)	0.39535 (6)	0.38958 (5)	0.02391 (16)
S1	0.17289 (19)	0.53716 (17)	0.50139 (15)	0.0268 (3)
S2	−0.1395 (2)	0.81122 (18)	0.38122 (16)	0.0351 (4)
C1	0.0610 (8)	0.8274 (7)	0.2998 (6)	0.0303 (14)
C2	0.0841 (10)	0.9543 (7)	0.1756 (7)	0.0432 (18)
H2	−0.0074	1.0308	0.1336	0.047 (7)*
C3	0.2405 (11)	0.9673 (9)	0.1148 (8)	0.059 (2)
H3	0.2534	1.0512	0.0301	0.047 (7)*
C4	0.3810 (10)	0.8571 (8)	0.1773 (8)	0.0493 (19)
H4	0.4874	0.8708	0.1386	0.047 (7)*
C5	0.3606 (8)	0.7277 (8)	0.2971 (7)	0.0383 (16)
H5	0.4525	0.6513	0.3383	0.047 (7)*
C6	0.1993 (8)	0.7127 (7)	0.3559 (6)	0.0281 (13)
C7	−0.2007 (9)	0.5887 (8)	0.1364 (7)	0.0479 (19)
H7A	−0.2818	0.5261	0.1556	0.084 (10)*
H7B	−0.1976	0.6533	0.0358	0.084 (10)*
H7C	−0.2308	0.6510	0.1909	0.084 (10)*
C8	−0.0340 (8)	0.4897 (8)	0.1781 (6)	0.0370 (16)
C9	−0.0118 (8)	0.3266 (7)	0.2412 (7)	0.0360 (15)
H9	−0.1032	0.2816	0.2532	0.047 (7)*
C10	0.1449 (8)	0.2336 (7)	0.2852 (6)	0.0312 (14)
H10	0.1544	0.1280	0.3285	0.047 (7)*
C11	0.2901 (8)	0.2954 (7)	0.2659 (6)	0.0306 (14)
C12	0.2665 (8)	0.4557 (7)	0.2059 (6)	0.0295 (14)
H12	0.3578	0.5005	0.1949	0.047 (7)*
C13	0.1079 (8)	0.5519 (7)	0.1614 (6)	0.0324 (15)
H13	0.0981	0.6576	0.1206	0.047 (7)*
C14	0.4597 (8)	0.1942 (7)	0.3057 (7)	0.0338 (15)
H14	0.4437	0.0884	0.3547	0.032 (17)*
C15	0.5498 (9)	0.2258 (8)	0.4069 (7)	0.0461 (18)
H15A	0.6561	0.1565	0.4283	0.084 (10)*
H15B	0.4838	0.2116	0.4943	0.084 (10)*
H15C	0.5665	0.3292	0.3623	0.084 (10)*
C16	0.5650 (9)	0.2064 (10)	0.1683 (8)	0.061 (2)
H16A	0.6731	0.1411	0.1928	0.084 (10)*
H16B	0.5776	0.3103	0.1148	0.084 (10)*
H16C	0.5104	0.1753	0.1109	0.084 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.0241 (3)	0.0240 (3)	0.0240 (2)	−0.00434 (18)	−0.00088 (18)	−0.01013 (19)
S1	0.0249 (8)	0.0311 (8)	0.0244 (7)	−0.0062 (7)	−0.0013 (6)	−0.0108 (7)
S2	0.0324 (9)	0.0306 (9)	0.0303 (8)	−0.0008 (7)	−0.0017 (7)	−0.0032 (7)
C1	0.040 (4)	0.027 (3)	0.028 (3)	−0.011 (3)	0.002 (3)	−0.012 (3)
C2	0.062 (5)	0.025 (3)	0.041 (4)	−0.014 (3)	0.002 (4)	−0.010 (3)
C3	0.087 (7)	0.041 (4)	0.046 (4)	−0.034 (5)	0.031 (5)	−0.013 (4)
C4	0.052 (5)	0.047 (5)	0.055 (5)	−0.031 (4)	0.020 (4)	−0.021 (4)
C5	0.035 (4)	0.042 (4)	0.046 (4)	−0.015 (3)	0.006 (3)	−0.024 (3)
C6	0.034 (4)	0.031 (3)	0.025 (3)	−0.013 (3)	0.000 (3)	−0.013 (3)
C7	0.038 (4)	0.059 (5)	0.041 (4)	0.006 (4)	−0.012 (3)	−0.020 (4)
C8	0.038 (4)	0.047 (4)	0.027 (3)	0.002 (3)	−0.005 (3)	−0.021 (3)
C9	0.038 (4)	0.039 (4)	0.039 (4)	−0.010 (3)	−0.001 (3)	−0.022 (3)
C10	0.035 (4)	0.029 (3)	0.036 (3)	−0.007 (3)	0.001 (3)	−0.019 (3)
C11	0.032 (4)	0.035 (4)	0.032 (3)	−0.007 (3)	0.001 (3)	−0.021 (3)
C12	0.032 (4)	0.034 (3)	0.027 (3)	−0.012 (3)	0.003 (3)	−0.014 (3)
C13	0.043 (4)	0.029 (3)	0.022 (3)	−0.005 (3)	0.001 (3)	−0.009 (3)
C14	0.029 (4)	0.032 (4)	0.042 (4)	−0.004 (3)	−0.002 (3)	−0.017 (3)
C15	0.039 (4)	0.053 (4)	0.048 (4)	−0.008 (3)	−0.009 (3)	−0.020 (4)
C16	0.036 (4)	0.087 (6)	0.061 (5)	0.006 (4)	0.003 (4)	−0.040 (5)

Geometric parameters (Å, º)

Ru1—C10	2.193 (6)	C7—H7A	0.96
Ru1—C12	2.201 (6)	C7—H7B	0.96
Ru1—C9	2.202 (6)	C7—H7C	0.96
Ru1—C13	2.210 (6)	C8—C13	1.402 (9)
Ru1—C8	2.233 (6)	C8—C9	1.430 (9)
Ru1—C11	2.254 (6)	C9—C10	1.398 (9)
Ru1—S1^i	2.364 (2)	C9—H9	0.93
Ru1—S2^i	2.386 (2)	C10—C11	1.421 (9)
Ru1—S1	2.3983 (19)	C10—H10	0.93
S1—C6	1.786 (6)	C11—C12	1.404 (8)
S1—Ru1^i	2.364 (2)	C11—C14	1.503 (9)
S2—C1	1.762 (6)	C12—C13	1.421 (9)
S2—Ru1^i	2.386 (2)	C12—H12	0.93
C1—C6	1.386 (9)	C13—H13	0.93
C1—C2	1.392 (8)	C14—C15	1.515 (9)
C2—C3	1.366 (10)	C14—C16	1.530 (9)
C2—H2	0.93	C14—H14	0.98
C3—C4	1.394 (11)	C15—H15A	0.96
C3—H3	0.93	C15—H15B	0.96
C4—C5	1.377 (9)	C15—H15C	0.96
C4—H4	0.93	C16—H16A	0.96
C5—C6	1.401 (9)	C16—H16B	0.96
C5—H5	0.93	C16—H16C	0.96
C7—C8	1.479 (9)
C10—Ru1—C12	66.2 (2)	C8—C7—H7B	109.5
C10—Ru1—C9	37.1 (2)	H7A—C7—H7B	109.5
C12—Ru1—C9	78.5 (2)	C8—C7—H7C	109.5
C10—Ru1—C13	78.8 (2)	H7A—C7—H7C	109.5
C12—Ru1—C13	37.6 (2)	H7B—C7—H7C	109.5
C9—Ru1—C13	66.5 (2)	C13—C8—C9	117.2 (6)
C10—Ru1—C8	67.6 (2)	C13—C8—C7	121.4 (6)
C12—Ru1—C8	67.2 (2)	C9—C8—C7	121.3 (7)
C9—Ru1—C8	37.6 (2)	C13—C8—Ru1	70.7 (3)
C13—Ru1—C8	36.8 (2)	C9—C8—Ru1	70.0 (4)
C10—Ru1—C11	37.2 (2)	C7—C8—Ru1	128.6 (4)
C12—Ru1—C11	36.7 (2)	C10—C9—C8	121.1 (6)
C9—Ru1—C11	67.2 (2)	C10—C9—Ru1	71.1 (4)
C13—Ru1—C11	67.3 (2)	C8—C9—Ru1	72.4 (4)
C8—Ru1—C11	80.2 (2)	C10—C9—H9	119.4
C10—Ru1—S1^i	126.15 (17)	C8—C9—H9	119.4
C12—Ru1—S1^i	148.78 (17)	Ru1—C9—H9	129.6
C9—Ru1—S1^i	96.85 (18)	C9—C10—C11	122.0 (6)
C13—Ru1—S1^i	112.16 (18)	C9—C10—Ru1	71.8 (3)
C8—Ru1—S1^i	90.12 (17)	C11—C10—Ru1	73.7 (3)
C11—Ru1—S1^i	163.21 (16)	C9—C10—H10	119.0
C10—Ru1—S2^i	90.39 (17)	C11—C10—H10	119.0
C12—Ru1—S2^i	126.29 (17)	Ru1—C10—H10	127.7
C9—Ru1—S2^i	111.65 (18)	C12—C11—C10	116.3 (6)
C13—Ru1—S2^i	163.45 (16)	C12—C11—C14	122.1 (6)
C8—Ru1—S2^i	147.87 (19)	C10—C11—C14	121.6 (6)
C11—Ru1—S2^i	96.50 (17)	C12—C11—Ru1	69.6 (3)
S1^i—Ru1—S2^i	84.33 (8)	C10—C11—Ru1	69.1 (3)
C10—Ru1—S1	151.04 (17)	C14—C11—Ru1	132.7 (4)
C12—Ru1—S1	94.91 (17)	C11—C12—C13	122.3 (6)
C9—Ru1—S1	164.62 (17)	C11—C12—Ru1	73.7 (3)
C13—Ru1—S1	99.85 (17)	C13—C12—Ru1	71.5 (3)
C8—Ru1—S1	127.01 (18)	C11—C12—H12	118.8
C11—Ru1—S1	115.27 (17)	C13—C12—H12	118.8
S1^i—Ru1—S1	81.51 (7)	Ru1—C12—H12	128.3
S2^i—Ru1—S1	83.48 (7)	C8—C13—C12	120.9 (6)
C6—S1—Ru1^i	103.6 (2)	C8—C13—Ru1	72.5 (3)
C6—S1—Ru1	104.32 (19)	C12—C13—Ru1	70.9 (3)
Ru1^i—S1—Ru1	98.49 (7)	C8—C13—H13	119.6
C1—S2—Ru1^i	104.1 (2)	C12—C13—H13	119.6
C6—C1—C2	118.2 (6)	Ru1—C13—H13	129.5
C6—C1—S2	121.0 (5)	C11—C14—C15	114.1 (5)
C2—C1—S2	120.9 (5)	C11—C14—C16	109.0 (5)
C3—C2—C1	120.4 (7)	C15—C14—C16	111.3 (6)
C3—C2—H2	119.8	C11—C14—H14	107.4
C1—C2—H2	119.8	C15—C14—H14	107.4
C2—C3—C4	121.3 (7)	C16—C14—H14	107.4
C2—C3—H3	119.4	C14—C15—H15A	109.5
C4—C3—H3	119.4	C14—C15—H15B	109.5
C5—C4—C3	119.3 (7)	H15A—C15—H15B	109.5
C5—C4—H4	120.4	C14—C15—H15C	109.5
C3—C4—H4	120.4	H15A—C15—H15C	109.5
C4—C5—C6	119.0 (7)	H15B—C15—H15C	109.5
C4—C5—H5	120.5	C14—C16—H16A	109.5
C6—C5—H5	120.5	C14—C16—H16B	109.5
C1—C6—C5	121.6 (6)	H16A—C16—H16B	109.5
C1—C6—S1	119.9 (5)	C14—C16—H16C	109.5
C5—C6—S1	118.4 (5)	H16A—C16—H16C	109.5
C8—C7—H7A	109.5	H16B—C16—H16C	109.5
C10—Ru1—S1—C6	89.4 (4)	S1—Ru1—C10—C9	−155.8 (3)
C12—Ru1—S1—C6	42.3 (3)	C12—Ru1—C10—C11	29.8 (3)
C9—Ru1—S1—C6	−21.5 (7)	C9—Ru1—C10—C11	132.7 (6)
C13—Ru1—S1—C6	4.7 (3)	C13—Ru1—C10—C11	67.1 (4)
C8—Ru1—S1—C6	−22.7 (3)	C8—Ru1—C10—C11	103.8 (4)
C11—Ru1—S1—C6	74.2 (3)	S1^i—Ru1—C10—C11	176.5 (3)
S1^i—Ru1—S1—C6	−106.4 (2)	S2^i—Ru1—C10—C11	−100.3 (3)
S2^i—Ru1—S1—C6	168.4 (2)	S1—Ru1—C10—C11	−23.1 (6)
C10—Ru1—S1—Ru1^i	−164.1 (3)	C9—C10—C11—C12	2.7 (8)
C12—Ru1—S1—Ru1^i	148.76 (17)	Ru1—C10—C11—C12	−52.7 (5)
C9—Ru1—S1—Ru1^i	84.9 (7)	C9—C10—C11—C14	−176.4 (5)
C13—Ru1—S1—Ru1^i	111.17 (18)	Ru1—C10—C11—C14	128.1 (5)
C8—Ru1—S1—Ru1^i	83.7 (2)	C9—C10—C11—Ru1	55.5 (5)
C11—Ru1—S1—Ru1^i	−179.35 (17)	C10—Ru1—C11—C12	130.4 (5)
S2^i—Ru1—S1—Ru1^i	−85.21 (8)	C9—Ru1—C11—C12	101.7 (4)
Ru1^i—S2—C1—C6	13.8 (5)	C13—Ru1—C11—C12	28.8 (4)
Ru1^i—S2—C1—C2	−167.6 (5)	C8—Ru1—C11—C12	64.8 (4)
C6—C1—C2—C3	−2.7 (10)	S1^i—Ru1—C11—C12	120.6 (5)
S2—C1—C2—C3	178.7 (6)	S2^i—Ru1—C11—C12	−147.5 (3)
C1—C2—C3—C4	−2.0 (11)	S1—Ru1—C11—C12	−61.7 (4)
C2—C3—C4—C5	4.5 (12)	C12—Ru1—C11—C10	−130.4 (5)
C3—C4—C5—C6	−2.2 (10)	C9—Ru1—C11—C10	−28.8 (4)
C2—C1—C6—C5	5.0 (9)	C13—Ru1—C11—C10	−101.7 (4)
S2—C1—C6—C5	−176.5 (5)	C8—Ru1—C11—C10	−65.7 (4)
C2—C1—C6—S1	−172.1 (5)	S1^i—Ru1—C11—C10	−9.9 (8)
S2—C1—C6—S1	6.4 (7)	S2^i—Ru1—C11—C10	82.0 (4)
C4—C5—C6—C1	−2.5 (9)	S1—Ru1—C11—C10	167.9 (3)
C4—C5—C6—S1	174.6 (5)	C10—Ru1—C11—C14	−114.2 (7)
Ru1^i—S1—C6—C1	−23.2 (5)	C12—Ru1—C11—C14	115.3 (7)
Ru1—S1—C6—C1	79.4 (5)	C9—Ru1—C11—C14	−143.0 (7)
Ru1^i—S1—C6—C5	159.6 (4)	C13—Ru1—C11—C14	144.1 (7)
Ru1—S1—C6—C5	−97.7 (5)	C8—Ru1—C11—C14	−179.9 (6)
C10—Ru1—C8—C13	−101.6 (4)	S1^i—Ru1—C11—C14	−124.1 (6)
C12—Ru1—C8—C13	−29.1 (3)	S2^i—Ru1—C11—C14	−32.2 (6)
C9—Ru1—C8—C13	−130.1 (5)	S1—Ru1—C11—C14	53.6 (6)
C11—Ru1—C8—C13	−65.0 (4)	C10—C11—C12—C13	−2.4 (8)
S1^i—Ru1—C8—C13	128.8 (3)	C14—C11—C12—C13	176.7 (5)
S2^i—Ru1—C8—C13	−151.7 (3)	Ru1—C11—C12—C13	−54.8 (5)
S1—Ru1—C8—C13	49.4 (4)	C10—C11—C12—Ru1	52.5 (5)
C10—Ru1—C8—C9	28.5 (4)	C14—C11—C12—Ru1	−128.4 (5)
C12—Ru1—C8—C9	101.0 (4)	C10—Ru1—C12—C11	−30.2 (4)
C13—Ru1—C8—C9	130.1 (5)	C9—Ru1—C12—C11	−67.1 (4)
C11—Ru1—C8—C9	65.1 (4)	C13—Ru1—C12—C11	−133.3 (5)
S1^i—Ru1—C8—C9	−101.1 (4)	C8—Ru1—C12—C11	−104.8 (4)
S2^i—Ru1—C8—C9	−21.6 (5)	S1^i—Ru1—C12—C11	−151.3 (3)
S1—Ru1—C8—C9	179.5 (3)	S2^i—Ru1—C12—C11	41.5 (4)
C10—Ru1—C8—C7	143.1 (7)	S1—Ru1—C12—C11	127.0 (3)
C12—Ru1—C8—C7	−144.3 (7)	C10—Ru1—C12—C13	103.0 (4)
C9—Ru1—C8—C7	114.7 (8)	C9—Ru1—C12—C13	66.2 (4)
C13—Ru1—C8—C7	−115.3 (8)	C8—Ru1—C12—C13	28.5 (4)
C11—Ru1—C8—C7	179.8 (7)	C11—Ru1—C12—C13	133.3 (5)
S1^i—Ru1—C8—C7	13.6 (6)	S1^i—Ru1—C12—C13	−18.1 (5)
S2^i—Ru1—C8—C7	93.1 (7)	S2^i—Ru1—C12—C13	174.7 (3)
S1—Ru1—C8—C7	−65.9 (7)	S1—Ru1—C12—C13	−99.8 (3)
C13—C8—C9—C10	0.4 (9)	C9—C8—C13—C12	−0.1 (8)
C7—C8—C9—C10	−177.7 (6)	C7—C8—C13—C12	178.0 (5)
Ru1—C8—C9—C10	−53.9 (5)	Ru1—C8—C13—C12	54.0 (5)
C13—C8—C9—Ru1	54.3 (5)	C9—C8—C13—Ru1	−54.0 (5)
C7—C8—C9—Ru1	−123.7 (6)	C7—C8—C13—Ru1	124.1 (6)
C12—Ru1—C9—C10	65.6 (4)	C11—C12—C13—C8	1.1 (9)
C13—Ru1—C9—C10	103.0 (4)	Ru1—C12—C13—C8	−54.7 (5)
C8—Ru1—C9—C10	133.0 (6)	C11—C12—C13—Ru1	55.8 (5)
C11—Ru1—C9—C10	28.9 (4)	C10—Ru1—C13—C8	67.4 (4)
S1^i—Ru1—C9—C10	−145.7 (3)	C12—Ru1—C13—C8	132.7 (5)
S2^i—Ru1—C9—C10	−59.1 (4)	C9—Ru1—C13—C8	30.6 (4)
S1—Ru1—C9—C10	131.4 (6)	C11—Ru1—C13—C8	104.6 (4)
C10—Ru1—C9—C8	−133.0 (6)	S1^i—Ru1—C13—C8	−57.3 (4)
C12—Ru1—C9—C8	−67.5 (4)	S2^i—Ru1—C13—C8	117.6 (6)
C13—Ru1—C9—C8	−30.0 (4)	S1—Ru1—C13—C8	−142.0 (3)
C11—Ru1—C9—C8	−104.2 (4)	C10—Ru1—C13—C12	−65.3 (4)
S1^i—Ru1—C9—C8	81.2 (4)	C9—Ru1—C13—C12	−102.1 (4)
S2^i—Ru1—C9—C8	167.8 (3)	C8—Ru1—C13—C12	−132.7 (5)
S1—Ru1—C9—C8	−1.6 (9)	C11—Ru1—C13—C12	−28.2 (3)
C8—C9—C10—C11	−1.9 (9)	S1^i—Ru1—C13—C12	170.0 (3)
Ru1—C9—C10—C11	−56.3 (5)	S2^i—Ru1—C13—C12	−15.1 (8)
C8—C9—C10—Ru1	54.5 (5)	S1—Ru1—C13—C12	85.2 (3)
C12—Ru1—C10—C9	−102.8 (4)	C12—C11—C14—C15	55.1 (8)
C13—Ru1—C10—C9	−65.6 (4)	C10—C11—C14—C15	−125.9 (6)
C8—Ru1—C10—C9	−28.8 (4)	Ru1—C11—C14—C15	−36.0 (9)
C11—Ru1—C10—C9	−132.7 (6)	C12—C11—C14—C16	−70.1 (7)
S1^i—Ru1—C10—C9	43.8 (4)	C10—C11—C14—C16	109.0 (7)
S2^i—Ru1—C10—C9	127.1 (4)	Ru1—C11—C14—C16	−161.2 (5)

Symmetry code: (i) −x, −y+1, −z+1.