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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m894.
Published online 2009 July 11. doi:  10.1107/S1600536809026063
PMCID: PMC2977155

trans-Di-μ-carbonyl-bis­{carbon­yl[η5-2,3,4,5-tetra­methyl-1-(2-thien­yl)cyclo­penta­dien­yl]ruthenium(I)}(RuRu)

Abstract

The title compound, [Ru2(C13H15S)2(CO)4], is a centrosymmetric binuclear metal–carbonyl complex containing an Ru—Ru single bond [2.7511 (8) Å]. Each RuI atom is coordinated by two bridging carbonyl ligands, one terminal carbonyl ligand and one η5-cyclo­penta­dienyl group. The complex has a trans conformation and the two cyclo­penta­dienyl ring planes are parallel. The crystal structure involves weak C—H(...)O hydrogen bonds.

Related literature

For general background to substituted cyclo­penta­dien­yl–metal complexes, see: Arndt (2002 [triangle]); Bailey et al. (1978 [triangle]); King (1976 [triangle]); Möhring & Coville (2006 [triangle]). For the crystal structures of related ruthenium complexes, see: Schumann et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m894-scheme1.jpg

Experimental

Crystal data

  • [Ru2(C13H15S)2(CO)4]
  • M r = 720.82
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m894-efi1.jpg
  • a = 8.269 (2) Å
  • b = 8.899 (3) Å
  • c = 10.056 (3) Å
  • α = 81.826 (4)°
  • β = 76.083 (5)°
  • γ = 82.876 (5)°
  • V = 707.9 (4) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.25 mm−1
  • T = 273 K
  • 0.15 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.835, T max = 0.885
  • 3667 measured reflections
  • 2493 independent reflections
  • 2431 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.027
  • wR(F 2) = 0.100
  • S = 1.03
  • 2493 reflections
  • 173 parameters
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.63 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809026063/hy2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026063/hy2205Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported financially by the Hebei Natural Science Foundation of China (No. B2008000150) and the Research Fund for the Doctoral Program of Hebei Normal University (No. L2005B18).

supplementary crystallographic information

Comment

Cyclopentadienyl metal complexes have been extensively investigated since ferrocene has been discovered. Replacement of the hydrogen atoms by other substituents alters both the steric and electronic influences of the H5-cyclopentadienyl ring, resulting in differing reactivity and stability of the substituted cyclopentadienyl metal complexes (Arndt, 2002; King, 1976). Especially for metallocene polymerization catalysts, the steric and electronic effects of the substituents on cyclopentadienyl ring greatly influence catalytic activity (Bailey et al., 1978; Möhring & Coville, 2006).

The title compound, [Ru2(C13H15S)2(CO)4], is a centrosymmetric binuclear metal–carbonyl complex containing an Ru—Ru single bond. As shown in Fig. 1, the cyclopentadienyl ring of the organic ligand coordinates to the RuI atom (Table 1), while the thienyl group acting as a substituent is uncoordinated. The Ru1—Cg1 distance is 1.911 (3) Å, where Cg1 is the centroid of the cyclopentadienyl ring. The Ru—Ru bond distance is 2.7511 (8) Å and agrees with that observed in the analogous structure [2.751 (1) Å] (Schumann et al., 2002). The two cyclopentadienyl rings are parallel by virtue of the center of symmetry. The complex has a trans conformation, with two bridging carbonyl ligands and two terminal carbonyl ligands. The crystal packing is stabilized by weak C—H···O hydrogen bonds (Table 2).

Experimental

A solution of 1-(2-thienyl)-2,3,4,5-tetramethylcyclopentadiene (0.288 g, 1.41 mmol) and Ru3(CO)12 (0.30 g, 0.47 mmol) in xylene (30 ml) was refluxed for 12 h. The solvent was removed under vacuum and the residue was chromatographed on an Al2O3 column using petroleum ether/dichloromethane (volume ratio = 1:3) as eluent. The red band was collected, and after several days red crystals were obtained (yield 0.142 g, 27.9%). Analysis calculated for C30H30O4Ru2S2: C 49.99, H 4.19%; found: C 49.94, H 4.21%.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (CH) and 0.96 (CH3) Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) -x, 1-y, 1-z.]

Crystal data

[Ru2(C13H15S)2(CO)4]Z = 1
Mr = 720.82F(000) = 362
Triclinic, P1Dx = 1.691 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.269 (2) ÅCell parameters from 1002 reflections
b = 8.899 (3) Åθ = 4.5–22.2°
c = 10.056 (3) ŵ = 1.25 mm1
α = 81.826 (4)°T = 273 K
β = 76.083 (5)°Block, red
γ = 82.876 (5)°0.15 × 0.12 × 0.10 mm
V = 707.9 (4) Å3

Data collection

Bruker SMART APEX CCD diffractometer2493 independent reflections
Radiation source: fine-focus sealed tube2431 reflections with I > 2σ(I)
graphiteRint = 0.016
[var phi] and ω scansθmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.835, Tmax = 0.885k = −10→10
3667 measured reflectionsl = −11→9

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.100w = 1/[σ2(Fo2) + (0.09P)2 + 0.0001P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2493 reflectionsΔρmax = 0.53 e Å3
173 parametersΔρmin = −0.63 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (3)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Ru1−0.01450 (2)0.40733 (2)0.623212 (18)0.02438 (17)
S10.40230 (13)0.12210 (13)0.86000 (11)0.0622 (3)
O1−0.1870 (5)0.1684 (4)0.5431 (3)0.0836 (10)
O20.2945 (3)0.3491 (3)0.4011 (3)0.0510 (6)
C10.1653 (3)0.4142 (3)0.4472 (3)0.0314 (6)
C2−0.1213 (4)0.2620 (4)0.5688 (3)0.0440 (8)
C30.1390 (3)0.2962 (3)0.7731 (3)0.0298 (6)
C40.1719 (3)0.4517 (3)0.7456 (3)0.0302 (6)
C50.0180 (4)0.5430 (3)0.7921 (3)0.0327 (6)
C6−0.1104 (4)0.4436 (3)0.8499 (3)0.0337 (6)
C7−0.0383 (4)0.2915 (4)0.8363 (3)0.0319 (6)
C80.2643 (4)0.1630 (3)0.7537 (3)0.0329 (6)
C90.2855 (4)0.0553 (4)0.6641 (4)0.0452 (8)
H90.22170.05500.59960.054*
C100.4219 (5)−0.0577 (4)0.6847 (5)0.0606 (10)
H100.4556−0.13930.63280.073*
C110.4936 (5)−0.0364 (5)0.7814 (5)0.0657 (11)
H110.5834−0.09920.80500.079*
C120.3402 (4)0.5088 (4)0.6853 (3)0.0423 (7)
H12A0.32760.60350.62800.063*
H12B0.41040.43520.63080.063*
H12C0.39050.52440.75830.063*
C13−0.0043 (5)0.7128 (4)0.7947 (4)0.0500 (8)
H13A−0.02940.73520.88850.075*
H13B−0.09460.75580.75230.075*
H13C0.09700.75580.74490.075*
C14−0.2858 (4)0.4923 (5)0.9167 (3)0.0504 (9)
H14A−0.35390.40980.92590.076*
H14B−0.32720.57830.86100.076*
H14C−0.29000.52021.00630.076*
C15−0.1239 (4)0.1515 (4)0.8928 (3)0.0439 (8)
H15A−0.12400.12820.98900.066*
H15B−0.06610.06810.84430.066*
H15C−0.23720.16770.88180.066*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ru10.0253 (2)0.0278 (2)0.0202 (2)−0.00256 (12)−0.00515 (12)−0.00352 (12)
S10.0550 (6)0.0681 (7)0.0699 (7)0.0124 (5)−0.0345 (5)−0.0105 (5)
O10.121 (3)0.074 (2)0.071 (2)−0.060 (2)−0.0269 (19)−0.0075 (16)
O20.0391 (13)0.0660 (17)0.0375 (13)0.0190 (12)−0.0024 (10)−0.0029 (11)
C10.0284 (14)0.0381 (15)0.0274 (14)0.0025 (11)−0.0075 (11)−0.0057 (12)
C20.056 (2)0.0469 (18)0.0334 (17)−0.0202 (16)−0.0128 (14)−0.0008 (14)
C30.0289 (14)0.0367 (14)0.0258 (14)−0.0035 (11)−0.0108 (11)−0.0023 (11)
C40.0323 (14)0.0360 (15)0.0242 (13)−0.0065 (11)−0.0093 (11)−0.0020 (11)
C50.0397 (15)0.0379 (16)0.0235 (14)0.0006 (12)−0.0123 (11)−0.0088 (12)
C60.0344 (15)0.0460 (17)0.0212 (13)−0.0002 (13)−0.0070 (11)−0.0070 (12)
C70.0310 (14)0.0416 (17)0.0211 (14)−0.0071 (12)−0.0033 (11)0.0017 (12)
C80.0322 (14)0.0367 (15)0.0290 (14)−0.0025 (11)−0.0091 (11)0.0013 (12)
C90.0489 (19)0.0351 (17)0.0497 (19)0.0096 (14)−0.0128 (15)−0.0076 (14)
C100.056 (2)0.045 (2)0.077 (3)0.0101 (17)−0.009 (2)−0.0149 (19)
C110.046 (2)0.058 (2)0.086 (3)0.0160 (18)−0.019 (2)0.005 (2)
C120.0353 (16)0.0540 (19)0.0393 (17)−0.0175 (14)−0.0081 (13)−0.0001 (14)
C130.068 (2)0.0416 (18)0.0459 (19)0.0010 (15)−0.0186 (16)−0.0176 (15)
C140.0393 (18)0.073 (2)0.0341 (17)0.0036 (16)0.0012 (14)−0.0136 (17)
C150.0439 (18)0.0474 (19)0.0400 (17)−0.0165 (15)−0.0109 (14)0.0095 (14)

Geometric parameters (Å, °)

Ru1—C12.018 (3)C6—C71.421 (4)
Ru1—C1i2.048 (3)C6—C141.484 (4)
Ru1—C21.862 (3)C7—C151.483 (4)
Ru1—C32.246 (3)C8—C91.374 (4)
Ru1—C42.291 (3)C9—C101.449 (5)
Ru1—C52.302 (3)C9—H90.9300
Ru1—C62.282 (3)C10—C111.300 (6)
Ru1—C72.217 (3)C10—H100.9300
Ru1—Ru1i2.7511 (8)C11—H110.9300
S1—C111.718 (4)C12—H12A0.9600
S1—C81.718 (3)C12—H12B0.9600
O1—C21.139 (4)C12—H12C0.9600
O2—C11.173 (3)C13—H13A0.9600
C1—Ru1i2.048 (3)C13—H13B0.9600
C3—C41.420 (4)C13—H13C0.9600
C3—C71.454 (4)C14—H14A0.9600
C3—C81.476 (4)C14—H14B0.9600
C4—C51.436 (4)C14—H14C0.9600
C4—C121.499 (4)C15—H15A0.9600
C5—C61.428 (4)C15—H15B0.9600
C5—C131.502 (4)C15—H15C0.9600
C2—Ru1—C192.57 (13)C6—C5—C13124.5 (3)
C2—Ru1—C1i93.27 (14)C4—C5—C13126.8 (3)
C1—Ru1—C1i94.85 (10)C6—C5—Ru171.09 (15)
C2—Ru1—C793.67 (13)C4—C5—Ru171.36 (15)
C1—Ru1—C7135.88 (11)C13—C5—Ru1128.18 (19)
C1i—Ru1—C7128.26 (11)C7—C6—C5107.8 (2)
C2—Ru1—C3110.26 (13)C7—C6—C14126.8 (3)
C1—Ru1—C399.57 (11)C5—C6—C14125.4 (3)
C1i—Ru1—C3151.61 (11)C7—C6—Ru169.11 (15)
C7—Ru1—C338.01 (10)C5—C6—Ru172.61 (15)
C2—Ru1—C6113.52 (13)C14—C6—Ru1125.5 (2)
C1—Ru1—C6151.57 (11)C6—C7—C3108.2 (3)
C1i—Ru1—C694.73 (11)C6—C7—C15125.8 (3)
C7—Ru1—C636.80 (10)C3—C7—C15125.7 (3)
C3—Ru1—C661.88 (10)C6—C7—Ru174.10 (16)
C2—Ru1—C4146.49 (13)C3—C7—Ru172.09 (15)
C1—Ru1—C491.03 (11)C15—C7—Ru1125.5 (2)
C1i—Ru1—C4119.61 (11)C9—C8—C3129.5 (3)
C7—Ru1—C461.83 (10)C9—C8—S1111.3 (2)
C3—Ru1—C436.45 (10)C3—C8—S1119.1 (2)
C6—Ru1—C461.06 (10)C8—C9—C10110.1 (3)
C2—Ru1—C5149.83 (12)C8—C9—H9125.0
C1—Ru1—C5116.93 (11)C10—C9—H9125.0
C1i—Ru1—C590.57 (11)C11—C10—C9114.9 (4)
C7—Ru1—C561.24 (11)C11—C10—H10122.6
C3—Ru1—C561.10 (10)C9—C10—H10122.6
C6—Ru1—C536.30 (11)C10—C11—S1111.7 (3)
C4—Ru1—C536.45 (10)C10—C11—H11124.1
C2—Ru1—Ru1i94.32 (10)S1—C11—H11124.1
C1—Ru1—Ru1i47.87 (8)C4—C12—H12A109.5
C1i—Ru1—Ru1i46.97 (8)C4—C12—H12B109.5
C7—Ru1—Ru1i170.96 (8)H12A—C12—H12B109.5
C3—Ru1—Ru1i140.96 (7)C4—C12—H12C109.5
C6—Ru1—Ru1i134.95 (8)H12A—C12—H12C109.5
C4—Ru1—Ru1i112.39 (7)H12B—C12—H12C109.5
C5—Ru1—Ru1i109.85 (8)C5—C13—H13A109.5
C11—S1—C891.94 (18)C5—C13—H13B109.5
O2—C1—Ru1139.3 (2)H13A—C13—H13B109.5
O2—C1—Ru1i135.5 (2)C5—C13—H13C109.5
Ru1—C1—Ru1i85.15 (10)H13A—C13—H13C109.5
O1—C2—Ru1175.9 (3)H13B—C13—H13C109.5
C4—C3—C7107.5 (2)C6—C14—H14A109.5
C4—C3—C8126.3 (2)C6—C14—H14B109.5
C7—C3—C8126.0 (3)H14A—C14—H14B109.5
C4—C3—Ru173.49 (15)C6—C14—H14C109.5
C7—C3—Ru169.90 (15)H14A—C14—H14C109.5
C8—C3—Ru1126.41 (19)H14B—C14—H14C109.5
C3—C4—C5108.1 (2)C7—C15—H15A109.5
C3—C4—C12125.5 (3)C7—C15—H15B109.5
C5—C4—C12126.3 (3)H15A—C15—H15B109.5
C3—C4—Ru170.06 (15)C7—C15—H15C109.5
C5—C4—Ru172.19 (16)H15A—C15—H15C109.5
C12—C4—Ru1125.7 (2)H15B—C15—H15C109.5
C6—C5—C4108.4 (3)
C2—Ru1—C1—O2−85.4 (4)Ru1i—Ru1—C5—C4−101.12 (15)
C1i—Ru1—C1—O2−178.9 (5)C2—Ru1—C5—C13−119.8 (4)
C7—Ru1—C1—O212.6 (5)C1—Ru1—C5—C1373.4 (3)
C3—Ru1—C1—O225.7 (4)C1i—Ru1—C5—C13−22.3 (3)
C6—Ru1—C1—O271.9 (5)C7—Ru1—C5—C13−156.8 (3)
C4—Ru1—C1—O261.3 (4)C3—Ru1—C5—C13159.6 (3)
C5—Ru1—C1—O288.0 (4)C6—Ru1—C5—C13−119.5 (4)
Ru1i—Ru1—C1—O2−178.9 (5)C4—Ru1—C5—C13122.6 (4)
C2—Ru1—C1—Ru1i93.50 (13)Ru1i—Ru1—C5—C1321.5 (3)
C1i—Ru1—C1—Ru1i0.0C4—C5—C6—C7−1.5 (3)
C7—Ru1—C1—Ru1i−168.55 (12)C13—C5—C6—C7−175.7 (3)
C3—Ru1—C1—Ru1i−155.46 (10)Ru1—C5—C6—C760.44 (19)
C6—Ru1—C1—Ru1i−109.3 (2)C4—C5—C6—C14176.4 (3)
C4—Ru1—C1—Ru1i−119.83 (10)C13—C5—C6—C142.2 (5)
C5—Ru1—C1—Ru1i−93.11 (11)Ru1—C5—C6—C14−121.6 (3)
C2—Ru1—C3—C4174.96 (17)C4—C5—C6—Ru1−61.97 (18)
C1—Ru1—C3—C478.61 (17)C13—C5—C6—Ru1123.9 (3)
C1i—Ru1—C3—C4−40.9 (3)C2—Ru1—C6—C762.3 (2)
C7—Ru1—C3—C4−116.2 (2)C1—Ru1—C6—C7−92.8 (3)
C6—Ru1—C3—C4−78.47 (17)C1i—Ru1—C6—C7157.92 (18)
C5—Ru1—C3—C4−36.95 (16)C3—Ru1—C6—C7−39.01 (17)
Ru1i—Ru1—C3—C449.3 (2)C4—Ru1—C6—C7−80.71 (18)
C2—Ru1—C3—C7−68.8 (2)C5—Ru1—C6—C7−117.6 (2)
C1—Ru1—C3—C7−165.16 (18)Ru1i—Ru1—C6—C7−174.32 (13)
C1i—Ru1—C3—C775.4 (3)C2—Ru1—C6—C5179.85 (18)
C6—Ru1—C3—C737.75 (17)C1—Ru1—C6—C524.8 (3)
C4—Ru1—C3—C7116.2 (2)C1i—Ru1—C6—C5−84.50 (18)
C5—Ru1—C3—C779.27 (18)C7—Ru1—C6—C5117.6 (2)
Ru1i—Ru1—C3—C7165.55 (13)C3—Ru1—C6—C578.57 (18)
C2—Ru1—C3—C851.7 (3)C4—Ru1—C6—C536.87 (16)
C1—Ru1—C3—C8−44.6 (3)Ru1i—Ru1—C6—C5−56.74 (19)
C1i—Ru1—C3—C8−164.1 (2)C2—Ru1—C6—C14−58.7 (3)
C7—Ru1—C3—C8120.5 (3)C1—Ru1—C6—C14146.3 (3)
C6—Ru1—C3—C8158.3 (3)C1i—Ru1—C6—C1436.9 (3)
C4—Ru1—C3—C8−123.2 (3)C7—Ru1—C6—C14−121.0 (4)
C5—Ru1—C3—C8−160.2 (3)C3—Ru1—C6—C14−160.0 (3)
Ru1i—Ru1—C3—C8−73.9 (3)C4—Ru1—C6—C14158.3 (3)
C7—C3—C4—C50.5 (3)C5—Ru1—C6—C14121.4 (4)
C8—C3—C4—C5−174.1 (3)Ru1i—Ru1—C6—C1464.7 (3)
Ru1—C3—C4—C562.55 (18)C5—C6—C7—C31.8 (3)
C7—C3—C4—C12177.7 (3)C14—C6—C7—C3−176.0 (3)
C8—C3—C4—C123.1 (4)Ru1—C6—C7—C364.53 (19)
Ru1—C3—C4—C12−120.3 (3)C5—C6—C7—C15174.8 (3)
C7—C3—C4—Ru1−62.02 (18)C14—C6—C7—C15−3.1 (5)
C8—C3—C4—Ru1123.4 (3)Ru1—C6—C7—C15−122.6 (3)
C2—Ru1—C4—C3−8.6 (3)C5—C6—C7—Ru1−62.68 (19)
C1—Ru1—C4—C3−104.80 (17)C14—C6—C7—Ru1119.4 (3)
C1i—Ru1—C4—C3159.04 (16)C4—C3—C7—C6−1.5 (3)
C7—Ru1—C4—C338.80 (16)C8—C3—C7—C6173.1 (3)
C6—Ru1—C4—C380.91 (17)Ru1—C3—C7—C6−65.85 (19)
C5—Ru1—C4—C3117.6 (2)C4—C3—C7—C15−174.4 (3)
Ru1i—Ru1—C4—C3−148.89 (13)C8—C3—C7—C150.2 (5)
C2—Ru1—C4—C5−126.2 (2)Ru1—C3—C7—C15121.2 (3)
C1—Ru1—C4—C5137.56 (18)C4—C3—C7—Ru164.38 (18)
C1i—Ru1—C4—C541.4 (2)C8—C3—C7—Ru1−121.0 (3)
C7—Ru1—C4—C5−78.84 (18)C2—Ru1—C7—C6−125.6 (2)
C3—Ru1—C4—C5−117.6 (2)C1—Ru1—C7—C6136.91 (19)
C6—Ru1—C4—C5−36.73 (17)C1i—Ru1—C7—C6−28.5 (2)
Ru1i—Ru1—C4—C593.47 (16)C3—Ru1—C7—C6115.6 (2)
C2—Ru1—C4—C12111.4 (3)C4—Ru1—C7—C678.44 (18)
C1—Ru1—C4—C1215.2 (3)C5—Ru1—C7—C636.77 (16)
C1i—Ru1—C4—C12−81.0 (3)C2—Ru1—C7—C3118.77 (19)
C7—Ru1—C4—C12158.8 (3)C1—Ru1—C7—C321.3 (3)
C3—Ru1—C4—C12120.0 (3)C1i—Ru1—C7—C3−144.14 (17)
C6—Ru1—C4—C12−159.1 (3)C6—Ru1—C7—C3−115.6 (2)
C5—Ru1—C4—C12−122.4 (3)C4—Ru1—C7—C3−37.20 (16)
Ru1i—Ru1—C4—C12−28.9 (3)C5—Ru1—C7—C3−78.87 (18)
C3—C4—C5—C60.6 (3)C2—Ru1—C7—C15−2.7 (3)
C12—C4—C5—C6−176.5 (3)C1—Ru1—C7—C15−100.2 (3)
Ru1—C4—C5—C661.80 (18)C1i—Ru1—C7—C1594.4 (3)
C3—C4—C5—C13174.6 (3)C3—Ru1—C7—C15−121.5 (3)
C12—C4—C5—C13−2.5 (4)C6—Ru1—C7—C15122.9 (3)
Ru1—C4—C5—C13−124.2 (3)C4—Ru1—C7—C15−158.7 (3)
C3—C4—C5—Ru1−61.19 (18)C5—Ru1—C7—C15159.7 (3)
C12—C4—C5—Ru1121.7 (3)C4—C3—C8—C9−114.8 (4)
C2—Ru1—C5—C6−0.3 (3)C7—C3—C8—C971.6 (5)
C1—Ru1—C5—C6−167.05 (16)Ru1—C3—C8—C9−18.8 (5)
C1i—Ru1—C5—C697.23 (18)C4—C3—C8—S169.0 (3)
C7—Ru1—C5—C6−37.27 (17)C7—C3—C8—S1−104.6 (3)
C3—Ru1—C5—C6−80.92 (18)Ru1—C3—C8—S1164.94 (16)
C4—Ru1—C5—C6−117.9 (2)C11—S1—C8—C91.7 (3)
Ru1i—Ru1—C5—C6141.01 (15)C11—S1—C8—C3178.6 (3)
C2—Ru1—C5—C4117.6 (3)C3—C8—C9—C10−178.1 (3)
C1—Ru1—C5—C4−49.17 (19)S1—C8—C9—C10−1.6 (4)
C1i—Ru1—C5—C4−144.90 (17)C8—C9—C10—C110.6 (5)
C7—Ru1—C5—C480.60 (18)C9—C10—C11—S10.7 (5)
C3—Ru1—C5—C436.96 (16)C8—S1—C11—C10−1.4 (4)
C6—Ru1—C5—C4117.9 (2)

Symmetry codes: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C10—H10···O2ii0.932.603.335 (5)136
C14—H14B···O2i0.962.583.319 (4)134

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2205).

References

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