supplementary materials


su2478 scheme

Acta Cryst. (2012). E68, m1164    [ doi:10.1107/S1600536812033454 ]

[[mu]-(3,4,5,6,7-[eta]:1,9,10,11,12)-5,11-Di-tert-butyl-2,2,8,8-tetramethyl-2,8-disilatricyclo[7.3.0.03,7]dodecatetraenediyl]bis[dicarbonylruthenium(I)]

B. Zhu

Abstract top

The title compound, [Ru2(C22H34Si2)(CO)4], contains two RuI atoms linked by a bridging ([eta]5-tBuC5H2)2(SiMe2)2 ligand (tBu is a tert-butyl and Me is a methyl group) with an Ru-Ru bond length of 2.8401 (7) Å. The dihedral angle between the planes of the cyclopentadienyl rings of the ligand is 123.13 (19)°. The four terminal carbonyl ligands are bound in a symmetrical and staggered array. In the crystal, molecules are linked via pairs of C-H...O hydrogen bonds, forming inversion dimers.

Comment top

Recently, a series of reactions of doubly-bridged ligand precursors (C5H4(E))(C5H4(E')) (E, E' = CH2, CMe2, SiMe2, or GeMe2) with Ru3(CO)12 have been reported by the group of Professor Angelici (Ovchinnikov et al., 2002) and our groups (Zhu et al., 2012), which generally afforded the corresponding doubly-bridged bis(cyclopentadienyl) dinuclear complex containing an elongated Ru—Ru bond. To develop a deeper understanding of the relationship between the structure of the ligand and the Ru—Ru bond distance, and make a comparison of the Ru—Ru bond distance with those in the respective non-bridged and singly-bridged bis(cyclopentadienyl) ruthenium analogues, we carried out the reaction of the doubly-bridged ligand precursor (tBuC5H3)2(SiMe2)2 with Ru3(CO)12 in refluxing xylene, which afforded the expected title product whose crystal structure we report on herein.

The molecular structure of title compound is presented in Fig. 1. It has approximate C2v symmetry, as reflected in the small torsion angle DCp(centroid)–Ru1–Ru2–Cp(centroid) (ca. 15.8°). The dihedral angle between the planes of the Cp rings of the (η5-C5H2tBu)2(SiMe2)2 ligand is rather large, 123.13 (19) °, which results in a longer than normal Ru1–Ru2 single bond distance of 2.8401 (7) Å, longer than that [2.8180 (3) Å] in its parent complex [(η5-C5H3)2(SiMe2)2]Ru2(CO)4 (Ovchinnikov et al., 2002). Therefore, the two tBu substituents on title compound have considerable effect on the geometry of the system.

The elongated Ru—Ru distance makes CO bridging unfavorable. This situation is similar to that in other doubly-bridged analogues, for example 2.8420 (8) Å in [(η5-C5H3)2(CMe2)(SiMe2)]Ru2(CO)4, 2.824 (1) Å in [(η5-C5H3)2(CMe2)(GeMe2)]Ru2(CO)4, 2.8382 (9) Å in [(η5-C5H3)2(CH2)(SiMe2)]Ru2(CO)4, 2.8429 (7) Å in [(η5-C5H3)2(CH2)(GeMe2)]Ru2(CO)4 (Zhu et al., 2012), and 2.821 (1) Å in the fulvalene diruthenium carbonyl complex (η5:η5-C10H8)Ru2(CO)4 (Boese et al., 1997).

Generally, due to the rigid structure of the doubly-bridged ligand, the Ru—Ru bond distances in the above-mentioned complexes are obviously longer than those in the respective non-bridged and singly-bridged analogues, for example 2.735 (2) Å in trans-[(η5-C5H5)Ru(CO)(µ-CO)]2 (Mills et al., 1967), 2.7879 (4) Å in (CMe2)[(η5-C5H4)Ru(CO)2]2 (Burger, 2001), or 2.705 Å in (SiMe2)[(η5-C5H4)Ru(CO)(µ-CO)]2 (Zhou et al., 1997; Bitterwolf et al., 1996).

Related literature top

For structures of non-bridged, singly-bridged, and doubly-bridged bis(cyclopentadienyl)ruthenium analogues of the title compound, see: Mills & Nice (1967); Burger (2001); Zhou et al. (1997); Bitterwolf et al. (1996); Ovchinnikov et al. (2002); Zhu et al. (2012). For the fulvalene diruthenium carbonyl complex (η5:η5-C10H8)Ru2(CO)4, see: Boese et al. (1997).

Experimental top

A solution of (C5H3tBu)(SiMe2))2 (80 mg, 0.22 mmol) and Ru3(CO)12 (80 mg, 0.13 mmol) in xylene (20 ml) was refluxed for 15 h. After removal of the solvent under reduced pressure, the residue, which was dissolved in a minimum amount of CH2Cl2, the solution was chromatographed on an alumina column using petroleum ether–CH2Cl2 (5:1) as eluent. A yellow band was eluted and collected. After removal of the solvents under vacuum from the above eluate, the residue was recrystallized from n-hexane/CH2Cl2 (1:1) at 263 K to give colourless crystals of the title compound (54 mg, 36%). Anal. Calcd for C26H34O4Ru2Si2: C, 46.69; H, 5.12. Found: C, 46.82; H, 5.17. Spectroscopic data for the title compound is given in the archived CIF.

Refinement top

All the hydrogen atoms could be located in difference electron density maps. In th final cycles of refinement they were included in calculated positions and treated as riding atoms: C-H = 0.98 and 1.00 Å for CH3 and CH H-atoms, respectively, with Uiso(H) = k × Ueq(parent C-atom), where k = 1.5 for CH3 H-atoms and = 1.2 for other H-atoms.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound with the atom numbering. Displacement ellipsoids are drawn at the 30% probability level.
[µ-(3,4,5,6,7-η:1,9,10,11,12)-5,11-Di-tert-butyl-2,2,8,8-tetramethyl- 2,8-disilatricyclo[7.3.0.03,7]dodecatetraenediyl]bis[dicarbonylruthenium(I)] top
Crystal data top
[Ru2(C22H34Si2)(CO)4]Z = 2
Mr = 668.85F(000) = 676
Triclinic, P1Dx = 1.605 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.632 (3) ÅCell parameters from 3308 reflections
b = 10.886 (3) Åθ = 2.4–28.3°
c = 14.546 (5) ŵ = 1.21 mm1
α = 89.518 (5)°T = 173 K
β = 71.581 (4)°Block, yellow
γ = 61.560 (4)°0.17 × 0.16 × 0.15 mm
V = 1384.0 (7) Å3
Data collection top
Bruker APEXII CCD
diffractometer
4802 independent reflections
Radiation source: fine-focus sealed tube4101 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1211
Tmin = 0.821, Tmax = 0.840k = 126
6921 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0409P)2]
where P = (Fo2 + 2Fc2)/3
4802 reflections(Δ/σ)max < 0.001
317 parametersΔρmax = 0.92 e Å3
0 restraintsΔρmin = 0.86 e Å3
Crystal data top
[Ru2(C22H34Si2)(CO)4]γ = 61.560 (4)°
Mr = 668.85V = 1384.0 (7) Å3
Triclinic, P1Z = 2
a = 10.632 (3) ÅMo Kα radiation
b = 10.886 (3) ŵ = 1.21 mm1
c = 14.546 (5) ÅT = 173 K
α = 89.518 (5)°0.17 × 0.16 × 0.15 mm
β = 71.581 (4)°
Data collection top
Bruker APEXII CCD
diffractometer
4802 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
4101 reflections with I > 2σ(I)
Tmin = 0.821, Tmax = 0.840Rint = 0.029
6921 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.077Δρmax = 0.92 e Å3
S = 1.04Δρmin = 0.86 e Å3
4802 reflectionsAbsolute structure: ?
317 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Experimental. Spectroscopic data for the title compound: 1H NMR (CDCl3): δ 5.26 (s, 4H, C5H2), 1.33 (s, 18H, C(CH3)3), 0.44 (s, 6H, Si(CH3)), 0.23 (s, 6H, Si(CH3)). IR (νCO): 2016(s), 1964(s), 1953(s), 1918(s) cm-1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
xyzUiso*/Ueq
Ru10.18780 (3)0.25054 (2)0.24573 (2)0.0120 (1)
Ru20.01860 (3)0.14546 (3)0.30871 (2)0.0119 (1)
Si10.05491 (10)0.22259 (9)0.06637 (7)0.0147 (2)
Si20.20390 (10)0.49039 (9)0.27597 (7)0.0155 (3)
O10.2229 (3)0.2477 (3)0.44361 (19)0.0323 (9)
O20.4503 (3)0.0461 (2)0.16495 (19)0.0268 (8)
O30.0771 (3)0.2370 (3)0.51910 (18)0.0369 (9)
O40.2411 (3)0.1387 (2)0.3097 (2)0.0320 (9)
C10.1049 (4)0.3370 (3)0.1239 (2)0.0144 (9)
C20.0009 (4)0.4414 (3)0.2140 (2)0.0135 (9)
C30.0875 (3)0.4865 (3)0.2459 (2)0.0140 (9)
C40.2440 (4)0.4151 (3)0.1790 (2)0.0147 (9)
C50.2514 (4)0.3265 (3)0.1043 (2)0.0148 (9)
C60.3673 (4)0.4458 (3)0.1819 (2)0.0144 (9)
C70.3545 (4)0.4787 (4)0.2878 (2)0.0205 (11)
C80.3461 (4)0.5772 (3)0.1329 (3)0.0222 (11)
C90.5264 (4)0.3196 (3)0.1258 (3)0.0204 (10)
C100.0830 (3)0.2036 (3)0.1740 (2)0.0138 (9)
C110.0919 (3)0.0804 (3)0.1964 (2)0.0124 (9)
C120.2045 (3)0.1098 (3)0.2926 (2)0.0152 (9)
C130.2670 (3)0.2564 (3)0.3280 (2)0.0141 (9)
C140.1938 (3)0.3164 (3)0.2584 (2)0.0141 (9)
C150.2601 (4)0.0125 (3)0.3415 (2)0.0153 (9)
C160.3307 (4)0.0588 (4)0.4535 (2)0.0262 (11)
C170.3792 (4)0.0198 (4)0.3014 (3)0.0267 (11)
C180.1273 (4)0.1413 (3)0.3170 (3)0.0210 (10)
C190.0376 (4)0.3094 (4)0.0237 (3)0.0242 (11)
C200.2232 (4)0.0455 (3)0.0048 (2)0.0220 (10)
C210.2787 (4)0.5623 (3)0.4091 (3)0.0237 (11)
C220.3234 (4)0.6240 (3)0.2140 (3)0.0261 (11)
C230.2077 (4)0.2457 (3)0.3686 (3)0.0219 (11)
C240.3476 (4)0.0650 (3)0.1998 (2)0.0165 (10)
C250.1445 (4)0.0298 (3)0.3083 (3)0.0189 (10)
C260.0499 (4)0.2012 (4)0.4378 (3)0.0226 (11)
H30.045400.559500.305000.0170*
H50.344500.267600.045000.0180*
H7A0.252400.558200.324500.0310*
H7B0.431900.503700.287300.0310*
H7C0.371200.395000.319200.0310*
H8A0.351700.558500.065500.0330*
H8B0.427000.597500.131500.0330*
H8C0.246100.658900.170400.0330*
H9A0.536600.234400.153600.0310*
H9B0.604700.339200.131700.0310*
H9C0.539600.304400.056300.0310*
H110.030900.013000.151200.0150*
H130.352900.310300.391700.0170*
H16A0.255200.059900.477900.0390*
H16B0.361500.007900.484000.0390*
H16C0.420600.154100.470300.0390*
H17A0.461400.118500.313400.0400*
H17B0.421600.038000.334500.0400*
H17C0.331100.016200.230600.0400*
H18A0.083300.173100.245700.0310*
H18B0.165400.202600.349300.0310*
H18C0.048400.146300.340600.0310*
H19A0.036700.318200.079700.0370*
H19B0.124900.403800.008200.0370*
H19C0.073200.251800.046800.0370*
H20A0.305700.057200.040500.0330*
H20B0.194300.005500.032000.0330*
H20C0.258300.008500.054400.0330*
H21A0.376700.565600.441200.0360*
H21B0.293700.658100.417200.0360*
H21C0.205300.501000.439200.0360*
H22A0.287100.584400.144400.0390*
H22B0.315400.709500.219300.0390*
H22C0.430400.648300.245600.0390*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.0114 (1)0.0114 (1)0.0144 (2)0.0058 (1)0.0059 (1)0.0043 (1)
Ru20.0112 (1)0.0122 (1)0.0127 (2)0.0060 (1)0.0045 (1)0.0041 (1)
Si10.0167 (4)0.0169 (4)0.0132 (4)0.0095 (4)0.0069 (4)0.0049 (4)
Si20.0113 (4)0.0105 (4)0.0237 (5)0.0045 (3)0.0067 (4)0.0036 (4)
O10.0476 (17)0.0405 (16)0.0266 (15)0.0297 (14)0.0226 (14)0.0152 (13)
O20.0179 (12)0.0184 (13)0.0359 (15)0.0051 (11)0.0060 (11)0.0046 (11)
O30.0342 (15)0.0594 (19)0.0155 (14)0.0219 (14)0.0090 (12)0.0016 (13)
O40.0219 (13)0.0200 (13)0.0533 (18)0.0085 (12)0.0159 (13)0.0177 (12)
C10.0159 (16)0.0147 (16)0.0168 (17)0.0103 (13)0.0066 (14)0.0086 (13)
C20.0137 (15)0.0096 (15)0.0185 (17)0.0062 (13)0.0068 (14)0.0058 (13)
C30.0158 (16)0.0088 (15)0.0181 (17)0.0057 (13)0.0075 (14)0.0032 (13)
C40.0181 (16)0.0127 (15)0.0146 (16)0.0086 (13)0.0060 (14)0.0071 (13)
C50.0187 (16)0.0167 (16)0.0133 (16)0.0118 (14)0.0060 (14)0.0055 (13)
C60.0159 (16)0.0169 (16)0.0152 (16)0.0109 (14)0.0068 (14)0.0031 (13)
C70.0236 (18)0.0253 (18)0.0234 (19)0.0166 (15)0.0143 (16)0.0055 (15)
C80.0194 (17)0.0210 (18)0.032 (2)0.0123 (15)0.0127 (16)0.0119 (16)
C90.0161 (17)0.0212 (17)0.0256 (19)0.0099 (14)0.0087 (15)0.0048 (15)
C100.0140 (16)0.0133 (15)0.0169 (17)0.0061 (13)0.0102 (14)0.0053 (13)
C110.0127 (15)0.0132 (15)0.0158 (16)0.0080 (13)0.0082 (13)0.0025 (13)
C120.0127 (15)0.0160 (16)0.0176 (17)0.0066 (13)0.0070 (14)0.0031 (13)
C130.0082 (14)0.0137 (16)0.0215 (17)0.0046 (13)0.0080 (13)0.0031 (13)
C140.0099 (15)0.0139 (16)0.0175 (17)0.0040 (13)0.0068 (13)0.0048 (13)
C150.0157 (16)0.0126 (15)0.0196 (17)0.0087 (13)0.0062 (14)0.0065 (13)
C160.032 (2)0.0204 (18)0.0217 (19)0.0150 (16)0.0009 (16)0.0039 (15)
C170.0237 (19)0.029 (2)0.039 (2)0.0179 (16)0.0178 (17)0.0178 (17)
C180.0185 (17)0.0165 (17)0.0252 (19)0.0086 (14)0.0047 (15)0.0088 (15)
C190.031 (2)0.030 (2)0.0216 (18)0.0191 (17)0.0154 (16)0.0109 (16)
C200.0219 (18)0.0234 (18)0.0202 (18)0.0117 (15)0.0061 (15)0.0003 (15)
C210.0208 (18)0.0196 (18)0.030 (2)0.0114 (15)0.0060 (16)0.0016 (15)
C220.0214 (18)0.0153 (17)0.045 (2)0.0094 (15)0.0155 (17)0.0089 (16)
C230.0251 (19)0.0179 (17)0.028 (2)0.0140 (15)0.0106 (17)0.0082 (15)
C240.0160 (17)0.0173 (17)0.0200 (17)0.0100 (15)0.0084 (14)0.0096 (14)
C250.0195 (17)0.0229 (18)0.0228 (18)0.0156 (16)0.0097 (15)0.0104 (15)
C260.0160 (17)0.0288 (19)0.025 (2)0.0124 (15)0.0079 (16)0.0075 (16)
Geometric parameters (Å, º) top
Ru1—Ru22.8401 (11)C12—C151.515 (5)
Ru1—C12.230 (3)C13—C141.426 (4)
Ru1—C22.260 (4)C15—C161.534 (4)
Ru1—C32.264 (3)C15—C171.523 (7)
Ru1—C42.265 (4)C15—C181.538 (5)
Ru1—C52.236 (3)C3—H31.0000
Ru1—C231.863 (4)C5—H51.0000
Ru1—C241.857 (3)C7—H7A0.9800
Ru2—C102.263 (3)C7—H7B0.9800
Ru2—C112.264 (3)C7—H7C0.9800
Ru2—C122.267 (4)C8—H8A0.9800
Ru2—C132.239 (4)C8—H8B0.9800
Ru2—C142.237 (3)C8—H8C0.9800
Ru2—C251.868 (3)C9—H9A0.9800
Ru2—C261.854 (4)C9—H9B0.9800
Si1—C11.861 (4)C9—H9C0.9800
Si1—C101.865 (3)C11—H111.0000
Si1—C191.867 (4)C13—H131.0000
Si1—C201.858 (3)C16—H16A0.9800
Si2—C21.871 (4)C16—H16B0.9800
Si2—C141.861 (3)C16—H16C0.9800
Si2—C211.859 (4)C17—H17A0.9800
Si2—C221.867 (4)C17—H17B0.9800
O1—C231.154 (5)C17—H17C0.9800
O2—C241.147 (4)C18—H18A0.9800
O3—C261.148 (5)C18—H18B0.9800
O4—C251.146 (4)C18—H18C0.9800
C1—C21.464 (4)C19—H19A0.9800
C1—C51.439 (6)C19—H19B0.9800
C2—C31.417 (6)C19—H19C0.9800
C3—C41.441 (5)C20—H20A0.9800
C4—C51.417 (5)C20—H20B0.9800
C4—C61.511 (6)C20—H20C0.9800
C6—C71.533 (4)C21—H21A0.9800
C6—C81.543 (4)C21—H21B0.9800
C6—C91.532 (5)C21—H21C0.9800
C10—C111.417 (4)C22—H22A0.9800
C10—C141.462 (4)C22—H22B0.9800
C11—C121.441 (4)C22—H22C0.9800
C12—C131.429 (4)
Ru2—Ru1—C192.46 (11)Si1—C10—C14123.8 (2)
Ru2—Ru1—C287.88 (11)C11—C10—C14107.0 (3)
Ru2—Ru1—C3117.71 (9)Ru2—C11—C1071.73 (18)
Ru2—Ru1—C4150.11 (11)Ru2—C11—C1271.53 (18)
Ru2—Ru1—C5127.88 (12)C10—C11—C12110.4 (2)
Ru2—Ru1—C2390.24 (14)Ru2—C12—C1171.4 (2)
Ru2—Ru1—C2488.90 (13)Ru2—C12—C1370.5 (2)
C1—Ru1—C238.06 (10)Ru2—C12—C15128.1 (2)
C1—Ru1—C362.19 (11)C11—C12—C13105.4 (3)
C1—Ru1—C462.96 (14)C11—C12—C15127.8 (3)
C1—Ru1—C537.60 (16)C13—C12—C15126.5 (3)
C1—Ru1—C23159.41 (12)Ru2—C13—C1272.6 (2)
C1—Ru1—C24108.96 (12)Ru2—C13—C1471.4 (2)
C2—Ru1—C336.51 (14)C12—C13—C14110.6 (3)
C2—Ru1—C462.34 (15)Ru2—C14—Si2113.04 (17)
C2—Ru1—C562.11 (13)Ru2—C14—C1072.03 (17)
C2—Ru1—C23121.78 (13)Ru2—C14—C1371.48 (18)
C2—Ru1—C24146.58 (13)Si2—C14—C10124.1 (2)
C3—Ru1—C437.11 (12)Si2—C14—C13128.4 (2)
C3—Ru1—C560.99 (10)C10—C14—C13106.6 (3)
C3—Ru1—C2398.65 (12)C12—C15—C16110.7 (3)
C3—Ru1—C24151.24 (14)C12—C15—C17107.6 (3)
C4—Ru1—C536.70 (12)C12—C15—C18110.7 (3)
C4—Ru1—C23107.05 (15)C16—C15—C17110.2 (3)
C4—Ru1—C24114.14 (15)C16—C15—C18108.8 (3)
C5—Ru1—C23141.38 (17)C17—C15—C18108.9 (3)
C5—Ru1—C2494.77 (12)Ru1—C23—O1176.4 (4)
C23—Ru1—C2491.48 (14)Ru1—C24—O2174.7 (3)
Ru1—Ru2—C1088.92 (9)Ru2—C25—O4177.7 (4)
Ru1—Ru2—C11118.88 (8)Ru2—C26—O3176.4 (4)
Ru1—Ru2—C12151.16 (7)Ru1—C3—H3125.00
Ru1—Ru2—C13127.78 (8)C2—C3—H3125.00
Ru1—Ru2—C1493.14 (9)C4—C3—H3125.00
Ru1—Ru2—C2589.05 (14)Ru1—C5—H5125.00
Ru1—Ru2—C2688.82 (15)C1—C5—H5125.00
C10—Ru2—C1136.47 (11)C4—C5—H5125.00
C10—Ru2—C1262.40 (11)C6—C7—H7A109.00
C10—Ru2—C1361.87 (11)C6—C7—H7B109.00
C10—Ru2—C1437.90 (10)C6—C7—H7C109.00
C10—Ru2—C25122.62 (15)H7A—C7—H7B110.00
C10—Ru2—C26148.19 (15)H7A—C7—H7C110.00
C11—Ru2—C1237.10 (11)H7B—C7—H7C109.00
C11—Ru2—C1360.93 (11)C6—C8—H8A109.00
C11—Ru2—C1461.88 (11)C6—C8—H8B110.00
C11—Ru2—C25100.00 (15)C6—C8—H8C110.00
C11—Ru2—C26150.71 (17)H8A—C8—H8B109.00
C12—Ru2—C1336.97 (11)H8A—C8—H8C109.00
C12—Ru2—C1462.81 (12)H8B—C8—H8C110.00
C12—Ru2—C25108.32 (16)C6—C9—H9A109.00
C12—Ru2—C26113.61 (17)C6—C9—H9B109.00
C13—Ru2—C1437.15 (11)C6—C9—H9C109.00
C13—Ru2—C25142.88 (16)H9A—C9—H9B109.00
C13—Ru2—C2695.42 (16)H9A—C9—H9C109.00
C14—Ru2—C25160.22 (15)H9B—C9—H9C110.00
C14—Ru2—C26110.62 (15)Ru2—C11—H11125.00
C25—Ru2—C2689.06 (18)C10—C11—H11125.00
C1—Si1—C10102.63 (14)C12—C11—H11125.00
C1—Si1—C19111.50 (17)Ru2—C13—H13125.00
C1—Si1—C20112.56 (19)C12—C13—H13125.00
C10—Si1—C19110.73 (19)C14—C13—H13125.00
C10—Si1—C20109.94 (14)C15—C16—H16A109.00
C19—Si1—C20109.34 (16)C15—C16—H16B109.00
C2—Si2—C14101.74 (15)C15—C16—H16C110.00
C2—Si2—C21112.61 (19)H16A—C16—H16B109.00
C2—Si2—C22109.47 (17)H16A—C16—H16C109.00
C14—Si2—C21110.45 (14)H16B—C16—H16C109.00
C14—Si2—C22113.01 (17)C15—C17—H17A109.00
C21—Si2—C22109.43 (17)C15—C17—H17B109.00
Ru1—C1—Si1112.78 (14)C15—C17—H17C109.00
Ru1—C1—C272.10 (18)H17A—C17—H17B110.00
Ru1—C1—C571.42 (19)H17A—C17—H17C109.00
Si1—C1—C2123.5 (3)H17B—C17—H17C110.00
Si1—C1—C5129.5 (2)C15—C18—H18A110.00
C2—C1—C5106.0 (3)C15—C18—H18B109.00
Ru1—C2—Si2120.17 (15)C15—C18—H18C109.00
Ru1—C2—C169.84 (18)H18A—C18—H18B110.00
Ru1—C2—C371.9 (2)H18A—C18—H18C109.00
Si2—C2—C1124.1 (3)H18B—C18—H18C109.00
Si2—C2—C3128.5 (2)Si1—C19—H19A109.00
C1—C2—C3107.3 (3)Si1—C19—H19B109.00
Ru1—C3—C271.62 (17)Si1—C19—H19C109.00
Ru1—C3—C471.51 (17)H19A—C19—H19B109.00
C2—C3—C4110.1 (3)H19A—C19—H19C110.00
Ru1—C4—C371.38 (19)H19B—C19—H19C109.00
Ru1—C4—C570.51 (19)Si1—C20—H20A109.00
Ru1—C4—C6129.1 (2)Si1—C20—H20B109.00
C3—C4—C5106.0 (4)Si1—C20—H20C109.00
C3—C4—C6125.9 (3)H20A—C20—H20B109.00
C5—C4—C6127.6 (3)H20A—C20—H20C109.00
Ru1—C5—C170.98 (17)H20B—C20—H20C110.00
Ru1—C5—C472.79 (17)Si2—C21—H21A109.00
C1—C5—C4110.5 (3)Si2—C21—H21B110.00
C4—C6—C7111.5 (3)Si2—C21—H21C109.00
C4—C6—C8107.7 (3)H21A—C21—H21B109.00
C4—C6—C9110.7 (3)H21A—C21—H21C109.00
C7—C6—C8108.5 (3)H21B—C21—H21C109.00
C7—C6—C9109.0 (3)Si2—C22—H22A109.00
C8—C6—C9109.5 (3)Si2—C22—H22B110.00
Ru2—C10—Si1118.11 (18)Si2—C22—H22C110.00
Ru2—C10—C1171.80 (17)H22A—C22—H22B109.00
Ru2—C10—C1470.08 (16)H22A—C22—H22C109.00
Si1—C10—C11128.8 (2)H22B—C22—H22C109.00
C1—Ru1—Ru2—C107.43 (11)C26—Ru2—C11—C10120.7 (3)
C1—Ru1—Ru2—C1129.18 (12)C26—Ru2—C11—C120.9 (4)
C1—Ru1—Ru2—C121.64 (17)Ru1—Ru2—C12—C1142.2 (2)
C1—Ru1—Ru2—C1344.89 (12)Ru1—Ru2—C12—C1372.5 (2)
C1—Ru1—Ru2—C1430.24 (10)Ru1—Ru2—C12—C15165.97 (16)
C1—Ru1—Ru2—C25130.09 (15)C10—Ru2—C12—C1135.62 (16)
C1—Ru1—Ru2—C26140.84 (15)C10—Ru2—C12—C1379.05 (17)
C2—Ru1—Ru2—C1045.23 (10)C10—Ru2—C12—C15159.4 (3)
C2—Ru1—Ru2—C1166.97 (11)C11—Ru2—C12—C13114.7 (2)
C2—Ru1—Ru2—C1239.44 (17)C11—Ru2—C12—C15123.8 (3)
C2—Ru1—Ru2—C137.10 (12)C13—Ru2—C12—C11114.7 (2)
C2—Ru1—Ru2—C147.55 (10)C13—Ru2—C12—C15121.5 (3)
C2—Ru1—Ru2—C25167.88 (15)C14—Ru2—C12—C1178.52 (17)
C2—Ru1—Ru2—C26103.04 (15)C14—Ru2—C12—C1336.14 (16)
C3—Ru1—Ru2—C1067.10 (11)C14—Ru2—C12—C15157.7 (3)
C3—Ru1—Ru2—C1188.85 (12)C25—Ru2—C12—C1182.3 (2)
C3—Ru1—Ru2—C1261.31 (17)C25—Ru2—C12—C13163.07 (19)
C3—Ru1—Ru2—C1314.78 (12)C25—Ru2—C12—C1541.6 (3)
C3—Ru1—Ru2—C1429.43 (11)C26—Ru2—C12—C11179.50 (19)
C3—Ru1—Ru2—C25170.24 (15)C26—Ru2—C12—C1365.8 (2)
C3—Ru1—Ru2—C2681.16 (15)C26—Ru2—C12—C1555.7 (3)
C4—Ru1—Ru2—C1040.45 (16)Ru1—Ru2—C13—C12144.40 (13)
C4—Ru1—Ru2—C1162.19 (17)Ru1—Ru2—C13—C1424.7 (2)
C4—Ru1—Ru2—C1234.7 (2)C10—Ru2—C13—C1280.59 (17)
C4—Ru1—Ru2—C1311.88 (17)C10—Ru2—C13—C1439.09 (17)
C4—Ru1—Ru2—C142.77 (16)C11—Ru2—C13—C1238.84 (16)
C4—Ru1—Ru2—C25163.10 (19)C11—Ru2—C13—C1480.84 (18)
C4—Ru1—Ru2—C26107.82 (19)C12—Ru2—C13—C14119.7 (2)
C5—Ru1—Ru2—C106.32 (12)C14—Ru2—C13—C12119.7 (2)
C5—Ru1—Ru2—C1115.43 (13)C25—Ru2—C13—C1227.3 (3)
C5—Ru1—Ru2—C1212.11 (18)C25—Ru2—C13—C14146.9 (3)
C5—Ru1—Ru2—C1358.64 (13)C26—Ru2—C13—C12122.88 (19)
C5—Ru1—Ru2—C1443.99 (12)C26—Ru2—C13—C14117.4 (2)
C5—Ru1—Ru2—C25116.34 (16)Ru1—Ru2—C14—Si236.01 (14)
C5—Ru1—Ru2—C26154.58 (16)Ru1—Ru2—C14—C1084.19 (18)
C23—Ru1—Ru2—C10167.02 (13)Ru1—Ru2—C14—C13160.67 (16)
C23—Ru1—Ru2—C11171.24 (13)C10—Ru2—C14—Si2120.2 (3)
C23—Ru1—Ru2—C12161.23 (18)C10—Ru2—C14—C13115.1 (3)
C23—Ru1—Ru2—C13114.70 (14)C11—Ru2—C14—Si2157.3 (2)
C23—Ru1—Ru2—C14129.34 (12)C11—Ru2—C14—C1037.08 (19)
C23—Ru1—Ru2—C2570.33 (16)C11—Ru2—C14—C1378.06 (19)
C23—Ru1—Ru2—C2618.75 (16)C12—Ru2—C14—Si2160.63 (18)
C24—Ru1—Ru2—C10101.50 (12)C12—Ru2—C14—C1079.2 (2)
C24—Ru1—Ru2—C1179.76 (13)C12—Ru2—C14—C1335.97 (17)
C24—Ru1—Ru2—C12107.29 (18)C13—Ru2—C14—Si2124.7 (2)
C24—Ru1—Ru2—C13153.83 (13)C13—Ru2—C14—C10115.1 (3)
C24—Ru1—Ru2—C14139.18 (12)C26—Ru2—C14—Si253.9 (2)
C24—Ru1—Ru2—C2521.15 (16)C26—Ru2—C14—C10174.1 (2)
C24—Ru1—Ru2—C26110.23 (16)C26—Ru2—C14—C1370.8 (2)
Ru2—Ru1—C1—Si136.22 (17)C10—Si1—C1—Ru154.0 (2)
Ru2—Ru1—C1—C283.4 (2)C10—Si1—C1—C229.0 (3)
Ru2—Ru1—C1—C5162.10 (15)C10—Si1—C1—C5138.2 (3)
C2—Ru1—C1—Si1119.6 (3)C19—Si1—C1—Ru1172.57 (18)
C2—Ru1—C1—C5114.5 (3)C19—Si1—C1—C289.6 (3)
C3—Ru1—C1—Si1156.5 (2)C19—Si1—C1—C5103.3 (3)
C3—Ru1—C1—C236.8 (2)C20—Si1—C1—Ru164.1 (2)
C3—Ru1—C1—C577.66 (19)C20—Si1—C1—C2147.1 (2)
C4—Ru1—C1—Si1161.5 (2)C20—Si1—C1—C520.0 (3)
C4—Ru1—C1—C278.9 (2)C1—Si1—C10—Ru248.10 (19)
C4—Ru1—C1—C535.65 (17)C1—Si1—C10—C11136.7 (3)
C5—Ru1—C1—Si1125.9 (2)C1—Si1—C10—C1435.8 (3)
C5—Ru1—C1—C2114.5 (3)C19—Si1—C10—Ru2167.21 (17)
C23—Ru1—C1—Si1133.5 (4)C19—Si1—C10—C11104.2 (3)
C23—Ru1—C1—C213.9 (6)C19—Si1—C10—C1483.4 (3)
C23—Ru1—C1—C5100.7 (5)C20—Si1—C10—Ru271.9 (2)
C24—Ru1—C1—Si153.5 (2)C20—Si1—C10—C1116.7 (4)
C24—Ru1—C1—C2173.1 (2)C20—Si1—C10—C14155.7 (3)
C24—Ru1—C1—C572.4 (2)C14—Si2—C2—Ru147.3 (2)
Ru2—Ru1—C2—Si221.74 (17)C14—Si2—C2—C137.6 (3)
Ru2—Ru1—C2—C196.7 (2)C14—Si2—C2—C3137.5 (3)
Ru2—Ru1—C2—C3146.33 (16)C21—Si2—C2—Ru170.9 (2)
C1—Ru1—C2—Si2118.5 (3)C21—Si2—C2—C1155.9 (2)
C1—Ru1—C2—C3117.0 (3)C21—Si2—C2—C319.2 (3)
C3—Ru1—C2—Si2124.6 (2)C22—Si2—C2—Ru1167.09 (18)
C3—Ru1—C2—C1117.0 (3)C22—Si2—C2—C182.2 (3)
C4—Ru1—C2—Si2161.0 (2)C22—Si2—C2—C3102.8 (3)
C4—Ru1—C2—C180.6 (2)C2—Si2—C14—Ru252.36 (17)
C4—Ru1—C2—C336.36 (17)C2—Si2—C14—C1030.9 (3)
C5—Ru1—C2—Si2157.4 (2)C2—Si2—C14—C13136.4 (3)
C5—Ru1—C2—C138.9 (2)C21—Si2—C14—Ru267.4 (2)
C5—Ru1—C2—C378.1 (2)C21—Si2—C14—C10150.7 (3)
C23—Ru1—C2—Si267.2 (3)C21—Si2—C14—C1316.6 (4)
C23—Ru1—C2—C1174.3 (2)C22—Si2—C14—Ru2169.62 (17)
C23—Ru1—C2—C357.4 (3)C22—Si2—C14—C1086.3 (3)
C24—Ru1—C2—Si2106.5 (3)C22—Si2—C14—C13106.3 (3)
C24—Ru1—C2—C111.9 (4)Ru1—C1—C2—Si2113.5 (2)
C24—Ru1—C2—C3128.9 (3)Ru1—C1—C2—C362.5 (2)
Ru2—Ru1—C3—C238.75 (18)Si1—C1—C2—Ru1105.9 (2)
Ru2—Ru1—C3—C4158.25 (17)Si1—C1—C2—Si27.6 (4)
C1—Ru1—C3—C238.41 (19)Si1—C1—C2—C3168.4 (2)
C1—Ru1—C3—C481.1 (2)C5—C1—C2—Ru163.8 (2)
C2—Ru1—C3—C4119.5 (3)C5—C1—C2—Si2177.3 (2)
C4—Ru1—C3—C2119.5 (3)C5—C1—C2—C31.3 (3)
C5—Ru1—C3—C281.4 (2)Ru1—C1—C5—C462.4 (2)
C5—Ru1—C3—C438.1 (2)Si1—C1—C5—Ru1104.6 (2)
C23—Ru1—C3—C2133.6 (2)Si1—C1—C5—C4167.0 (2)
C23—Ru1—C3—C4106.9 (2)C2—C1—C5—Ru164.29 (19)
C24—Ru1—C3—C2117.0 (3)C2—C1—C5—C41.9 (3)
C24—Ru1—C3—C42.5 (4)Ru1—C2—C3—C461.5 (2)
Ru2—Ru1—C4—C341.2 (3)Si2—C2—C3—Ru1114.5 (2)
Ru2—Ru1—C4—C574.2 (3)Si2—C2—C3—C4176.0 (2)
Ru2—Ru1—C4—C6162.69 (17)C1—C2—C3—Ru161.20 (19)
C1—Ru1—C4—C378.8 (2)C1—C2—C3—C40.3 (3)
C1—Ru1—C4—C536.5 (2)Ru1—C3—C4—C562.4 (2)
C1—Ru1—C4—C6159.6 (3)Ru1—C3—C4—C6125.3 (3)
C2—Ru1—C4—C335.78 (18)C2—C3—C4—Ru161.6 (2)
C2—Ru1—C4—C579.6 (2)C2—C3—C4—C50.9 (3)
C2—Ru1—C4—C6157.3 (3)C2—C3—C4—C6173.2 (3)
C3—Ru1—C4—C5115.4 (3)Ru1—C4—C5—C161.3 (2)
C3—Ru1—C4—C6121.5 (3)C3—C4—C5—Ru163.0 (2)
C5—Ru1—C4—C3115.4 (3)C3—C4—C5—C11.7 (3)
C5—Ru1—C4—C6123.1 (4)C6—C4—C5—Ru1124.9 (3)
C23—Ru1—C4—C381.7 (2)C6—C4—C5—C1173.9 (3)
C23—Ru1—C4—C5163.0 (2)Ru1—C4—C6—C756.1 (3)
C23—Ru1—C4—C639.8 (3)Ru1—C4—C6—C8175.0 (2)
C24—Ru1—C4—C3178.7 (2)Ru1—C4—C6—C965.3 (3)
C24—Ru1—C4—C563.3 (3)C3—C4—C6—C738.4 (4)
C24—Ru1—C4—C659.8 (3)C3—C4—C6—C880.4 (3)
Ru2—Ru1—C5—C122.90 (19)C3—C4—C6—C9159.9 (3)
Ru2—Ru1—C5—C4142.6 (2)C5—C4—C6—C7150.9 (3)
C1—Ru1—C5—C4119.7 (3)C5—C4—C6—C890.3 (4)
C2—Ru1—C5—C139.40 (18)C5—C4—C6—C929.4 (4)
C2—Ru1—C5—C480.3 (2)Ru2—C10—C11—C1261.4 (2)
C3—Ru1—C5—C181.12 (19)Si1—C10—C11—Ru2111.8 (3)
C3—Ru1—C5—C438.6 (2)Si1—C10—C11—C12173.3 (3)
C4—Ru1—C5—C1119.7 (3)C14—C10—C11—Ru261.6 (2)
C23—Ru1—C5—C1146.4 (2)C14—C10—C11—C120.2 (4)
C23—Ru1—C5—C426.7 (3)Ru2—C10—C14—Si2106.1 (3)
C24—Ru1—C5—C1115.2 (2)Ru2—C10—C14—C1363.6 (2)
C24—Ru1—C5—C4125.1 (3)Si1—C10—C14—Ru2111.1 (3)
Ru1—Ru2—C10—Si122.01 (14)Si1—C10—C14—Si25.0 (4)
Ru1—Ru2—C10—C11146.93 (18)Si1—C10—C14—C13174.7 (2)
Ru1—Ru2—C10—C1496.51 (18)C11—C10—C14—Ru262.7 (2)
C11—Ru2—C10—Si1124.9 (3)C11—C10—C14—Si2168.8 (2)
C11—Ru2—C10—C14116.6 (3)C11—C10—C14—C130.9 (4)
C12—Ru2—C10—Si1161.1 (2)Ru2—C11—C12—C1362.7 (2)
C12—Ru2—C10—C1136.22 (18)Ru2—C11—C12—C15124.2 (4)
C12—Ru2—C10—C1480.3 (2)C10—C11—C12—Ru261.6 (2)
C13—Ru2—C10—Si1156.8 (2)C10—C11—C12—C131.1 (4)
C13—Ru2—C10—C1178.3 (2)C10—C11—C12—C15174.2 (3)
C13—Ru2—C10—C1438.31 (19)Ru2—C12—C13—C1461.6 (3)
C14—Ru2—C10—Si1118.5 (3)C11—C12—C13—Ru263.3 (2)
C14—Ru2—C10—C11116.6 (3)C11—C12—C13—C141.7 (4)
C25—Ru2—C10—Si166.2 (2)C15—C12—C13—Ru2123.5 (3)
C25—Ru2—C10—C1158.7 (3)C15—C12—C13—C14174.9 (3)
C25—Ru2—C10—C14175.3 (2)Ru2—C12—C15—C1663.2 (4)
C26—Ru2—C10—Si1108.0 (3)Ru2—C12—C15—C17176.4 (2)
C26—Ru2—C10—C11127.1 (3)Ru2—C12—C15—C1857.5 (3)
C26—Ru2—C10—C1410.5 (4)C11—C12—C15—C16158.5 (4)
Ru1—Ru2—C11—C1038.5 (2)C11—C12—C15—C1781.0 (4)
Ru1—Ru2—C11—C12158.30 (14)C11—C12—C15—C1837.8 (5)
C10—Ru2—C11—C12119.8 (3)C13—C12—C15—C1629.7 (5)
C12—Ru2—C11—C10119.8 (3)C13—C12—C15—C1790.7 (4)
C13—Ru2—C11—C1081.06 (19)C13—C12—C15—C18150.4 (3)
C13—Ru2—C11—C1238.71 (17)Ru2—C13—C14—Si2105.2 (3)
C14—Ru2—C11—C1038.53 (18)Ru2—C13—C14—C1064.0 (2)
C14—Ru2—C11—C1281.23 (18)C12—C13—C14—Ru262.3 (2)
C25—Ru2—C11—C10133.0 (2)C12—C13—C14—Si2167.5 (3)
C25—Ru2—C11—C12107.2 (2)C12—C13—C14—C101.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20A···O2i0.982.603.571 (5)171
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20A···O2i0.982.603.571 (5)171
Symmetry code: (i) x+1, y, z.
Acknowledgements top

The author gratefully acknowledges financial support from the National Natural Science Foundation of China (No. 21002069), the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry, and the Talent Fund Projects for Introduced Scholars in Tianjin Normal University (No. 5RL088).

references
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