supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2008). E64, m1454    [ doi:10.1107/S1600536808034211 ]

Tricarbonylbis(tricyclohexylphosphine-[kappa]P)ruthenium(0) toluene solvate

A. Nader, H. Görls and W. Imhof

Abstract top

The title compound, [Ru(C18H33P)2(CO)3]·C7H8, shows a distorted trigonal-bipyramdial coordination around the central Ru atom, with the two phosphine ligands occupying the axial positions. Two toluene molecules per asymmetric unit with site-occupation factors of 0.5 are observed. One of them forces two of the CO ligands to enclose a wider C-Ru-C bond angle [127.5 (3)°] than in the solvent-free crystal structure of [Ru(PCy3)2(CO)3] (Cy is cyclohexyl).

Comment top

In the course of a study whether Ru(II) complexes might act as suitable pre-catalysts in the reaction of α,β-unsaturated imines with carbon monoxide and ethylene to produce chiral γ-lactams, which is originally catalyzed by Ru(0) compounds (Berger & Imhof, 1999; Dönnecke & Imhof, 2003), we intended to use the non-classical Ru(II) complex [Ru(PCy3)2(H2)2(H)2] (Chaudret & Poilblanc, 1985) as the precatalyst. After cooling down the autoclave a white precipitate of the title compound was collected. This means that obviously carbon monoxide has replaced all dihydrogen and hydride ligands and the ruthenium center has been reduced from Ru(II) to Ru(0).

The molecular structure of the title compound has been published before as a solvent free crystal structure (P21/n, Dunne et al., 2004) with one disordered cyclohexyl ring. The synthesis at that time followed a literature procedure that used RuCl3.H2O, KOH, PCy3 and formaldehyde as reducing agent and source of carbon monoxide (Song & Trogler, 1992). The bond lengths in both structures are identical within systematic errors. Nevertheless, the C—Ru—C bond angles in the Ru(CO)3 plane are significantly different with 119.74 (9)°, 116.77 (9)° and 123.49 (9)° in the case of the structure reported by Dunne et al. whereas the corresponding angles in (I) measure to 109.3 (3)°, 123.2 (2)° and 127.5 (3)°. This difference is most probably caused by one of the disordered toluene solvent molecules being situated between two cyclohexyl rings of the phosphine ligands therefore leading to the highest observed bond angle of 127.6 (3)° (C2—Ru1—C3, Figure 1). In addition, one of the aromatic hydrogen atoms shows a weak C—H···O interaction towards one of the carbon monoxide ligands (H2TA···O2 = 2.09 (2) Å).

Related literature top

For background, see: Berger & Imhof (1999), Dönnecke & Imhof (2003), Chaudret & Poilblanc (1985), Song & Trogler (1992). For the solvent-free structure, see: Dunne et al. (2004).

Experimental top

In an attempt to catalytically react methyl-(3-phenylallylidene)amine with carbon monoxide and ethylene, 1 mmol of the imine together with 0.03 mmol (20 mg) [Ru(PCy3)2(H2)2(H)2] were dissolved in 4 ml toluene and were heated to 413 K for 17 h in an autoclave pressurized with 8 bar ethylene and 12 bar carbon monoxide. After cooling down the autoclave a white precipitate had formed which was collected and recrystallized from toluene to give colourless prisms of (I) (yield based on Ru: 48%).

Refinement top

The two solvent toluene molecules have been refined isotropically with sof's of 0.5 and have been constrained to be regular hexagons by AFIX 66 instructions in SHELXL. Hydrogen atoms were placed in idealized positions and refined as riding with Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: XP (Siemens, 1990).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) with isplacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.
Tricarbonylbis(tricyclohexylphosphine-κP)ruthenium(0) toluene solvate top
Crystal data top
[Ru(C18H33P)2(CO)3]·C7H8Z = 2
Mr = 838.06F(000) = 896
Triclinic, P1Dx = 1.169 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.4367 (6) ÅCell parameters from 16612 reflections
b = 12.4980 (4) Åθ = 2.2–27.5°
c = 16.2970 (7) ŵ = 0.43 mm−1
α = 92.685 (2)°T = 183 K
β = 103.594 (2)°Prism, colourless
γ = 103.500 (2)°0.08 × 0.06 × 0.05 mm
V = 2380.2 (2) Å3
Data collection top
Nonius KappaCCD
diffractometer		7032 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
graphiteθmax = 27.5°, θmin = 2.3°
φ and ω scansh = −16→15
16605 measured reflectionsk = −16→16
10678 independent reflectionsl = −21→21
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)] = 0.082Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.243H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.123P)2 + 7.5629P]
where P = (Fo2 + 2Fc2)/3
10678 reflections(Δ/σ)max < 0.001
438 parametersΔρmax = 3.45 e Å−3
0 restraintsΔρmin = −0.64 e Å−3
Crystal data top
[Ru(C18H33P)2(CO)3]·C7H8γ = 103.500 (2)°
Mr = 838.06V = 2380.2 (2) Å3
Triclinic, P1Z = 2
a = 12.4367 (6) ÅMo Kα radiation
b = 12.4980 (4) ŵ = 0.43 mm−1
c = 16.2970 (7) ÅT = 183 K
α = 92.685 (2)°0.08 × 0.06 × 0.05 mm
β = 103.594 (2)°
Data collection top
Nonius KappaCCD
diffractometer		7032 reflections with I > 2σ(I)
16605 measured reflectionsRint = 0.051
10678 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.082H-atom parameters constrained
wR(F2) = 0.243Δρmax = 3.45 e Å−3
S = 1.05Δρmin = −0.64 e Å−3
10678 reflectionsAbsolute structure: ?
438 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
Ru10.13721 (4)0.23221 (4)0.23002 (3)0.01644 (16)
P1−0.01593 (12)0.08021 (12)0.23565 (9)0.0150 (3)
P20.29082 (12)0.38833 (12)0.23373 (9)0.0155 (3)
O1−0.0288 (5)0.3806 (4)0.1972 (3)0.0409 (13)
O20.2609 (5)0.1948 (4)0.4093 (3)0.0409 (13)
O30.1465 (4)0.1397 (4)0.0545 (3)0.0308 (11)
C10.0340 (5)0.3249 (5)0.2116 (4)0.0233 (13)
C20.2164 (5)0.2079 (5)0.3409 (4)0.0233 (13)
C30.1466 (5)0.1712 (5)0.1227 (4)0.0219 (13)
C4−0.0556 (5)0.0908 (5)0.3394 (4)0.0200 (12)
H4A0.01510.09200.38430.024*
C5−0.0852 (6)0.2003 (5)0.3570 (4)0.0263 (14)
H5A−0.15390.20450.31320.032*
H5B−0.02120.26240.35300.032*
C6−0.1078 (7)0.2126 (6)0.4456 (4)0.0357 (17)
H6A−0.03640.21760.48970.043*
H6B−0.13170.28190.45300.043*
C7−0.1996 (7)0.1160 (6)0.4570 (5)0.0383 (18)
H7A−0.27290.11470.41630.046*
H7B−0.20990.12450.51520.046*
C8−0.1670 (7)0.0065 (7)0.4425 (5)0.0410 (19)
H8A−0.09620.00580.48540.049*
H8B−0.2287−0.05630.44890.049*
C9−0.1485 (6)−0.0064 (6)0.3538 (4)0.0320 (16)
H9A−0.2212−0.01100.31110.038*
H9B−0.1261−0.07630.34560.038*
C10−0.1535 (5)0.0670 (5)0.1531 (4)0.0205 (12)
H10A−0.19490.11510.17740.025*
C11−0.1395 (6)0.1110 (5)0.0687 (4)0.0230 (13)
H11A−0.08940.18720.07990.028*
H11B−0.10300.06370.03960.028*
C12−0.2566 (6)0.1113 (6)0.0115 (4)0.0292 (15)
H12A−0.28910.16420.03880.035*
H12B−0.24630.1374−0.04330.035*
C13−0.3400 (6)−0.0013 (6)−0.0056 (4)0.0316 (15)
H13A−0.41550.0045−0.03920.038*
H13B−0.3127−0.0527−0.03900.038*
C14−0.3518 (5)−0.0462 (6)0.0773 (4)0.0301 (15)
H14A−0.4032−0.12170.06540.036*
H14B−0.38690.00120.10770.036*
C15−0.2352 (5)−0.0500 (5)0.1343 (4)0.0263 (14)
H15A−0.2017−0.10050.10550.032*
H15B−0.2456−0.07880.18820.032*
C160.0086 (5)−0.0600 (4)0.2290 (4)0.0175 (12)
H16A−0.0650−0.11320.22940.021*
C170.0376 (6)−0.0909 (5)0.1457 (4)0.0226 (13)
H17A0.1146−0.04600.14570.027*
H17B−0.0183−0.07420.09700.027*
C180.0350 (6)−0.2138 (5)0.1360 (4)0.0295 (15)
H18A−0.0433−0.25870.13220.035*
H18B0.0555−0.23190.08280.035*
C190.1188 (7)−0.2425 (6)0.2115 (5)0.0390 (18)
H19A0.1092−0.32360.20720.047*
H19B0.1979−0.20730.20930.047*
C200.1012 (7)−0.2042 (6)0.2962 (5)0.0384 (18)
H20A0.1632−0.21610.34270.046*
H20B0.0278−0.24970.30320.046*
C210.0998 (6)−0.0801 (5)0.3039 (4)0.0292 (15)
H21A0.0826−0.06020.35800.035*
H21B0.1758−0.03330.30350.035*
C220.2621 (5)0.4827 (5)0.1498 (4)0.0196 (12)
H22A0.22370.53490.17280.024*
C230.3703 (6)0.5562 (5)0.1305 (4)0.0287 (15)
H23A0.40930.50910.10380.034*
H23B0.42380.59520.18420.034*
C240.3370 (6)0.6416 (5)0.0703 (4)0.0334 (16)
H24A0.30120.69070.09830.040*
H24B0.40670.68790.05830.040*
C250.2547 (6)0.5848 (6)−0.0122 (4)0.0321 (16)
H25A0.29260.5407−0.04270.039*
H25B0.23230.6412−0.04870.039*
C260.1487 (6)0.5097 (6)0.0043 (5)0.0330 (16)
H26A0.09820.4700−0.05020.040*
H26B0.10630.55520.02890.040*
C270.1789 (5)0.4252 (5)0.0652 (4)0.0234 (13)
H27A0.21420.37470.03820.028*
H27B0.10810.38030.07650.028*
C280.3294 (5)0.4788 (5)0.3363 (4)0.0203 (12)
H28A0.34920.43050.38180.024*
C290.4342 (6)0.5777 (5)0.3506 (4)0.0299 (15)
H29A0.50050.55130.34250.036*
H29B0.41860.62990.30820.036*
C300.4633 (6)0.6376 (6)0.4396 (5)0.0376 (18)
H30A0.53030.70150.44660.045*
H30B0.48390.58690.48200.045*
C310.3628 (7)0.6782 (6)0.4553 (5)0.0380 (18)
H31A0.38250.71410.51420.046*
H31B0.34600.73360.41600.046*
C320.2599 (7)0.5832 (6)0.4417 (5)0.0362 (17)
H32A0.19420.61130.44890.043*
H32B0.27440.53230.48540.043*
C330.2292 (6)0.5190 (6)0.3534 (4)0.0288 (15)
H33A0.20570.56740.30980.035*
H33B0.16350.45460.34890.035*
C340.4301 (5)0.3614 (5)0.2278 (4)0.0203 (12)
H34A0.48320.43480.22710.024*
C350.4209 (5)0.2904 (5)0.1459 (4)0.0259 (14)
H35A0.38340.32290.09620.031*
H35B0.37360.21480.14600.031*
C360.5405 (6)0.2846 (6)0.1388 (4)0.0337 (16)
H36A0.53350.23690.08660.040*
H36B0.58570.35960.13450.040*
C370.6021 (6)0.2384 (7)0.2154 (5)0.0399 (18)
H37A0.68150.24280.21200.048*
H37B0.56330.15950.21460.048*
C380.6047 (6)0.3024 (6)0.2994 (4)0.0308 (15)
H38A0.63830.26510.34760.037*
H38B0.65420.37810.30430.037*
C390.4861 (6)0.3095 (6)0.3051 (4)0.0274 (14)
H39A0.49200.35520.35800.033*
H39B0.43840.23460.30650.033*
C1TA0.4931 (7)−0.0455 (6)0.3912 (4)0.014 (2)*0.50
C2TA0.4173 (7)0.0083 (7)0.3442 (5)0.032 (3)*0.50
H2TA0.38510.05620.37230.038*0.50
C3TA0.3887 (8)−0.0082 (8)0.2560 (5)0.053 (4)*0.50
H3TA0.33690.02850.22380.063*0.50
C4TA0.4358 (8)−0.0784 (8)0.2148 (4)0.025 (3)*0.50
H4TA0.4162−0.08960.15460.030*0.50
C5TA0.5116 (8)−0.1322 (7)0.2619 (5)0.045 (4)*0.50
H5TA0.5438−0.18010.23380.054*0.50
C6TA0.5402 (7)−0.1157 (7)0.3501 (5)0.024 (3)*0.50
H6TA0.5920−0.15240.38230.028*0.50
C7TA0.5189 (9)−0.0327 (9)0.4744 (6)0.012 (2)*0.50
H7TA0.47940.01920.49350.017*0.50
H7TB0.6017−0.00340.49640.017*0.50
H7TC0.4949−0.10430.49540.017*0.50
C1TB0.2465 (7)0.3731 (7)−0.2461 (4)0.030 (3)*0.50
C2TB0.1736 (7)0.4430 (7)−0.2509 (4)0.022 (2)*0.50
H2TB0.16340.4756−0.20040.026*0.50
C3TB0.1159 (7)0.4651 (7)−0.3297 (5)0.032 (3)*0.50
H3TB0.06610.5129−0.33300.038*0.50
C4TB0.1309 (8)0.4173 (8)−0.4035 (4)0.047 (4)*0.50
H4TB0.09140.4324−0.45740.056*0.50
C5TB0.2038 (8)0.3474 (8)−0.3987 (4)0.031 (3)*0.50
H5TB0.21410.3148−0.44920.038*0.50
C6TB0.2615 (8)0.3253 (7)−0.3199 (5)0.041 (4)*0.50
H6TB0.31130.2776−0.31660.049*0.50
C7TB0.3013 (13)0.3540 (12)−0.1693 (9)0.035 (3)*0.50
H7TD0.27960.3945−0.12540.053*0.50
H7TE0.38400.3791−0.16240.053*0.50
H7TF0.28060.2746−0.16380.053*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.0155 (3)0.0161 (2)0.0170 (3)0.00294 (18)0.00400 (18)0.00047 (17)
P10.0145 (8)0.0157 (7)0.0146 (7)0.0036 (6)0.0033 (6)0.0013 (6)
P20.0138 (7)0.0156 (7)0.0160 (7)0.0030 (6)0.0026 (6)0.0011 (6)
O10.039 (3)0.042 (3)0.047 (3)0.025 (3)0.006 (3)0.006 (2)
O20.036 (3)0.050 (3)0.026 (3)0.003 (2)−0.005 (2)0.008 (2)
O30.035 (3)0.033 (3)0.024 (2)0.005 (2)0.011 (2)−0.005 (2)
C10.021 (3)0.028 (3)0.021 (3)0.005 (3)0.006 (3)0.003 (3)
C20.019 (3)0.024 (3)0.023 (3)−0.001 (3)0.003 (3)0.001 (3)
C30.020 (3)0.021 (3)0.023 (3)0.002 (2)0.003 (3)0.003 (3)
C40.016 (3)0.028 (3)0.017 (3)0.007 (2)0.004 (2)0.003 (2)
C50.031 (4)0.021 (3)0.031 (4)0.006 (3)0.015 (3)0.006 (3)
C60.039 (4)0.043 (4)0.029 (4)0.012 (3)0.017 (3)−0.007 (3)
C70.045 (5)0.056 (5)0.024 (4)0.022 (4)0.017 (3)0.009 (3)
C80.049 (5)0.051 (5)0.039 (4)0.022 (4)0.029 (4)0.022 (4)
C90.037 (4)0.031 (4)0.033 (4)0.006 (3)0.021 (3)0.008 (3)
C100.019 (3)0.019 (3)0.023 (3)0.005 (2)0.005 (2)0.002 (2)
C110.028 (4)0.022 (3)0.016 (3)0.005 (3)0.001 (3)0.006 (2)
C120.030 (4)0.032 (3)0.023 (3)0.011 (3)−0.001 (3)0.002 (3)
C130.022 (4)0.037 (4)0.033 (4)0.009 (3)0.001 (3)−0.001 (3)
C140.015 (3)0.037 (4)0.030 (4)−0.002 (3)0.001 (3)−0.002 (3)
C150.018 (3)0.026 (3)0.028 (3)−0.003 (3)0.001 (3)0.001 (3)
C160.017 (3)0.014 (3)0.019 (3)0.002 (2)0.001 (2)0.001 (2)
C170.027 (3)0.021 (3)0.023 (3)0.012 (3)0.006 (3)0.003 (2)
C180.034 (4)0.022 (3)0.037 (4)0.013 (3)0.011 (3)0.001 (3)
C190.048 (5)0.030 (4)0.047 (5)0.025 (3)0.013 (4)0.002 (3)
C200.048 (5)0.035 (4)0.034 (4)0.024 (4)0.002 (3)0.005 (3)
C210.035 (4)0.027 (3)0.027 (3)0.016 (3)0.003 (3)0.003 (3)
C220.020 (3)0.015 (3)0.023 (3)0.001 (2)0.007 (2)0.004 (2)
C230.024 (4)0.028 (3)0.027 (3)−0.004 (3)0.003 (3)0.003 (3)
C240.038 (4)0.023 (3)0.032 (4)−0.001 (3)0.002 (3)0.012 (3)
C250.041 (4)0.029 (3)0.022 (3)0.006 (3)0.003 (3)0.010 (3)
C260.029 (4)0.038 (4)0.031 (4)0.007 (3)0.004 (3)0.008 (3)
C270.024 (3)0.020 (3)0.025 (3)0.003 (3)0.007 (3)0.007 (3)
C280.024 (3)0.022 (3)0.013 (3)0.007 (3)0.000 (2)0.002 (2)
C290.024 (4)0.023 (3)0.036 (4)−0.001 (3)0.005 (3)−0.011 (3)
C300.035 (4)0.030 (4)0.038 (4)0.005 (3)−0.004 (3)−0.014 (3)
C310.047 (5)0.033 (4)0.030 (4)0.013 (3)0.003 (3)−0.010 (3)
C320.050 (5)0.033 (4)0.031 (4)0.015 (3)0.019 (3)−0.002 (3)
C330.029 (4)0.030 (3)0.027 (3)0.010 (3)0.006 (3)−0.006 (3)
C340.016 (3)0.021 (3)0.023 (3)0.003 (2)0.005 (2)0.000 (2)
C350.022 (3)0.032 (3)0.026 (3)0.009 (3)0.010 (3)−0.003 (3)
C360.026 (4)0.045 (4)0.031 (4)0.012 (3)0.006 (3)−0.004 (3)
C370.027 (4)0.055 (5)0.048 (5)0.025 (4)0.015 (3)0.011 (4)
C380.022 (4)0.046 (4)0.027 (4)0.017 (3)0.001 (3)0.011 (3)
C390.027 (4)0.039 (4)0.022 (3)0.018 (3)0.007 (3)0.008 (3)
Geometric parameters (Å, °) top
Ru1—C11.903 (6)C24—H24B0.9900
Ru1—C31.915 (6)C25—C261.518 (10)
Ru1—C21.919 (7)C25—H25A0.9900
Ru1—P12.3777 (15)C25—H25B0.9900
Ru1—P22.3780 (15)C26—C271.532 (9)
P1—C161.849 (6)C26—H26A0.9900
P1—C41.877 (6)C26—H26B0.9900
P1—C101.878 (6)C27—H27A0.9900
P2—C341.862 (6)C27—H27B0.9900
P2—C281.869 (6)C28—C331.527 (9)
P2—C221.873 (6)C28—C291.536 (9)
O1—C11.155 (8)C28—H28A1.0000
O2—C21.160 (8)C29—C301.523 (9)
O3—C31.161 (7)C29—H29A0.9900
C4—C51.529 (8)C29—H29B0.9900
C4—C91.537 (9)C30—C311.523 (10)
C4—H4A1.0000C30—H30A0.9900
C5—C61.543 (8)C30—H30B0.9900
C5—H5A0.9900C31—C321.493 (11)
C5—H5B0.9900C31—H31A0.9900
C6—C71.507 (11)C31—H31B0.9900
C6—H6A0.9900C32—C331.533 (9)
C6—H6B0.9900C32—H32A0.9900
C7—C81.538 (10)C32—H32B0.9900
C7—H7A0.9900C33—H33A0.9900
C7—H7B0.9900C33—H33B0.9900
C8—C91.523 (9)C34—C351.535 (8)
C8—H8A0.9900C34—C391.538 (9)
C8—H8B0.9900C34—H34A1.0000
C9—H9A0.9900C35—C361.536 (9)
C9—H9B0.9900C35—H35A0.9900
C10—C111.538 (8)C35—H35B0.9900
C10—C151.544 (8)C36—C371.517 (11)
C10—H10A1.0000C36—H36A0.9900
C11—C121.535 (9)C36—H36B0.9900
C11—H11A0.9900C37—C381.543 (10)
C11—H11B0.9900C37—H37A0.9900
C12—C131.510 (10)C37—H37B0.9900
C12—H12A0.9900C38—C391.522 (9)
C12—H12B0.9900C38—H38A0.9900
C13—C141.512 (10)C38—H38B0.9900
C13—H13A0.9900C39—H39A0.9900
C13—H13B0.9900C39—H39B0.9900
C14—C151.540 (9)C1TA—C7TA1.310 (12)
C14—H14A0.9900C1TA—C2TA1.3900
C14—H14B0.9900C1TA—C6TA1.3900
C15—H15A0.9900C2TA—C3TA1.3900
C15—H15B0.9900C2TA—H2TA0.9500
C16—C211.534 (9)C3TA—C4TA1.3900
C16—C171.539 (8)C3TA—H3TA0.9500
C16—H16A1.0000C4TA—C5TA1.3900
C17—C181.529 (8)C4TA—H4TA0.9500
C17—H17A0.9900C5TA—C6TA1.3900
C17—H17B0.9900C5TA—H5TA0.9500
C18—C191.531 (10)C6TA—H6TA0.9500
C18—H18A0.9900C7TA—H7TA0.9800
C18—H18B0.9900C7TA—H7TB0.9800
C19—C201.520 (10)C7TA—H7TC0.9800
C19—H19A0.9900C1TB—C7TB1.338 (16)
C19—H19B0.9900C1TB—C2TB1.3900
C20—C211.554 (9)C1TB—C6TB1.3900
C20—H20A0.9900C2TB—C3TB1.3900
C20—H20B0.9900C2TB—H2TB0.9500
C21—H21A0.9900C3TB—C4TB1.3900
C21—H21B0.9900C3TB—H3TB0.9500
C22—C271.543 (8)C4TB—C5TB1.3900
C22—C231.549 (8)C4TB—H4TB0.9500
C22—H22A1.0000C5TB—C6TB1.3900
C23—C241.545 (9)C5TB—H5TB0.9500
C23—H23A0.9900C6TB—H6TB0.9500
C23—H23B0.9900C7TB—H7TD0.9800
C24—C251.512 (9)C7TB—H7TE0.9800
C24—H24A0.9900C7TB—H7TF0.9800
C1—Ru1—C3109.3 (3)C25—C24—C23111.1 (5)
C1—Ru1—C2123.2 (3)C25—C24—H24A109.4
C3—Ru1—C2127.5 (3)C23—C24—H24A109.4
C1—Ru1—P189.69 (19)C25—C24—H24B109.4
C3—Ru1—P192.00 (18)C23—C24—H24B109.4
C2—Ru1—P188.51 (18)H24A—C24—H24B108.0
C1—Ru1—P289.56 (19)C24—C25—C26110.6 (6)
C3—Ru1—P291.75 (18)C24—C25—H25A109.5
C2—Ru1—P288.80 (18)C26—C25—H25A109.5
P1—Ru1—P2176.22 (5)C24—C25—H25B109.5
C16—P1—C4102.8 (3)C26—C25—H25B109.5
C16—P1—C10103.9 (3)H25A—C25—H25B108.1
C4—P1—C10104.3 (3)C25—C26—C27111.8 (6)
C16—P1—Ru1117.59 (19)C25—C26—H26A109.3
C4—P1—Ru1111.03 (19)C27—C26—H26A109.3
C10—P1—Ru1115.62 (19)C25—C26—H26B109.3
C34—P2—C28102.7 (3)C27—C26—H26B109.3
C34—P2—C22104.2 (3)H26A—C26—H26B107.9
C28—P2—C22104.7 (3)C26—C27—C22111.4 (5)
C34—P2—Ru1117.4 (2)C26—C27—H27A109.4
C28—P2—Ru1110.9 (2)C22—C27—H27A109.4
C22—P2—Ru1115.46 (19)C26—C27—H27B109.4
O1—C1—Ru1177.3 (6)C22—C27—H27B109.4
O2—C2—Ru1177.1 (6)H27A—C27—H27B108.0
O3—C3—Ru1174.3 (6)C33—C28—C29109.2 (5)
C5—C4—C9110.1 (5)C33—C28—P2113.0 (4)
C5—C4—P1112.2 (4)C29—C28—P2116.6 (4)
C9—C4—P1116.4 (4)C33—C28—H28A105.7
C5—C4—H4A105.8C29—C28—H28A105.7
C9—C4—H4A105.8P2—C28—H28A105.7
P1—C4—H4A105.8C30—C29—C28111.3 (6)
C4—C5—C6111.9 (5)C30—C29—H29A109.4
C4—C5—H5A109.2C28—C29—H29A109.4
C6—C5—H5A109.2C30—C29—H29B109.4
C4—C5—H5B109.2C28—C29—H29B109.4
C6—C5—H5B109.2H29A—C29—H29B108.0
H5A—C5—H5B107.9C29—C30—C31111.1 (6)
C7—C6—C5111.4 (6)C29—C30—H30A109.4
C7—C6—H6A109.4C31—C30—H30A109.4
C5—C6—H6A109.4C29—C30—H30B109.4
C7—C6—H6B109.4C31—C30—H30B109.4
C5—C6—H6B109.4H30A—C30—H30B108.0
H6A—C6—H6B108.0C32—C31—C30110.0 (6)
C6—C7—C8110.5 (6)C32—C31—H31A109.7
C6—C7—H7A109.5C30—C31—H31A109.7
C8—C7—H7A109.5C32—C31—H31B109.7
C6—C7—H7B109.5C30—C31—H31B109.7
C8—C7—H7B109.5H31A—C31—H31B108.2
H7A—C7—H7B108.1C31—C32—C33112.4 (6)
C9—C8—C7110.0 (6)C31—C32—H32A109.1
C9—C8—H8A109.7C33—C32—H32A109.1
C7—C8—H8A109.7C31—C32—H32B109.1
C9—C8—H8B109.7C33—C32—H32B109.1
C7—C8—H8B109.7H32A—C32—H32B107.9
H8A—C8—H8B108.2C28—C33—C32111.8 (6)
C8—C9—C4111.9 (6)C28—C33—H33A109.3
C8—C9—H9A109.2C32—C33—H33A109.3
C4—C9—H9A109.2C28—C33—H33B109.3
C8—C9—H9B109.2C32—C33—H33B109.3
C4—C9—H9B109.2H33A—C33—H33B107.9
H9A—C9—H9B107.9C35—C34—C39109.6 (5)
C11—C10—C15108.9 (5)C35—C34—P2112.6 (4)
C11—C10—P1114.9 (4)C39—C34—P2113.5 (4)
C15—C10—P1115.1 (4)C35—C34—H34A106.9
C11—C10—H10A105.7C39—C34—H34A106.9
C15—C10—H10A105.7P2—C34—H34A106.9
P1—C10—H10A105.7C34—C35—C36110.1 (5)
C12—C11—C10110.1 (5)C34—C35—H35A109.6
C12—C11—H11A109.6C36—C35—H35A109.6
C10—C11—H11A109.6C34—C35—H35B109.6
C12—C11—H11B109.6C36—C35—H35B109.6
C10—C11—H11B109.6H35A—C35—H35B108.2
H11A—C11—H11B108.2C37—C36—C35111.1 (6)
C13—C12—C11113.0 (6)C37—C36—H36A109.4
C13—C12—H12A109.0C35—C36—H36A109.4
C11—C12—H12A109.0C37—C36—H36B109.4
C13—C12—H12B109.0C35—C36—H36B109.4
C11—C12—H12B109.0H36A—C36—H36B108.0
H12A—C12—H12B107.8C36—C37—C38111.7 (6)
C12—C13—C14110.1 (6)C36—C37—H37A109.3
C12—C13—H13A109.6C38—C37—H37A109.3
C14—C13—H13A109.6C36—C37—H37B109.3
C12—C13—H13B109.6C38—C37—H37B109.3
C14—C13—H13B109.6H37A—C37—H37B107.9
H13A—C13—H13B108.2C39—C38—C37112.3 (6)
C13—C14—C15111.6 (5)C39—C38—H38A109.1
C13—C14—H14A109.3C37—C38—H38A109.1
C15—C14—H14A109.3C39—C38—H38B109.1
C13—C14—H14B109.3C37—C38—H38B109.1
C15—C14—H14B109.3H38A—C38—H38B107.9
H14A—C14—H14B108.0C38—C39—C34109.7 (5)
C14—C15—C10110.1 (5)C38—C39—H39A109.7
C14—C15—H15A109.6C34—C39—H39A109.7
C10—C15—H15A109.6C38—C39—H39B109.7
C14—C15—H15B109.6C34—C39—H39B109.7
C10—C15—H15B109.6H39A—C39—H39B108.2
H15A—C15—H15B108.2C7TA—C1TA—C2TA120.6 (7)
C21—C16—C17108.8 (5)C7TA—C1TA—C6TA119.3 (7)
C21—C16—P1114.6 (4)C2TA—C1TA—C6TA120.0
C17—C16—P1112.8 (4)C3TA—C2TA—C1TA120.0
C21—C16—H16A106.7C3TA—C2TA—H2TA120.0
C17—C16—H16A106.7C1TA—C2TA—H2TA120.0
P1—C16—H16A106.7C2TA—C3TA—C4TA120.0
C18—C17—C16110.5 (5)C2TA—C3TA—H3TA120.0
C18—C17—H17A109.5C4TA—C3TA—H3TA120.0
C16—C17—H17A109.5C3TA—C4TA—C5TA120.0
C18—C17—H17B109.5C3TA—C4TA—H4TA120.0
C16—C17—H17B109.5C5TA—C4TA—H4TA120.0
H17A—C17—H17B108.1C4TA—C5TA—C6TA120.0
C17—C18—C19110.6 (6)C4TA—C5TA—H5TA120.0
C17—C18—H18A109.5C6TA—C5TA—H5TA120.0
C19—C18—H18A109.5C5TA—C6TA—C1TA120.0
C17—C18—H18B109.5C5TA—C6TA—H6TA120.0
C19—C18—H18B109.5C1TA—C6TA—H6TA120.0
H18A—C18—H18B108.1C1TA—C7TA—H7TA109.5
C20—C19—C18112.4 (6)C1TA—C7TA—H7TB109.5
C20—C19—H19A109.1H7TA—C7TA—H7TB109.5
C18—C19—H19A109.1C1TA—C7TA—H7TC109.5
C20—C19—H19B109.1H7TA—C7TA—H7TC109.5
C18—C19—H19B109.1H7TB—C7TA—H7TC109.5
H19A—C19—H19B107.9C7TB—C1TB—C2TB118.5 (8)
C19—C20—C21112.6 (6)C7TB—C1TB—C6TB121.5 (8)
C19—C20—H20A109.1C2TB—C1TB—C6TB120.0
C21—C20—H20A109.1C1TB—C2TB—C3TB120.0
C19—C20—H20B109.1C1TB—C2TB—H2TB120.0
C21—C20—H20B109.1C3TB—C2TB—H2TB120.0
H20A—C20—H20B107.8C4TB—C3TB—C2TB120.0
C16—C21—C20109.2 (5)C4TB—C3TB—H3TB120.0
C16—C21—H21A109.8C2TB—C3TB—H3TB120.0
C20—C21—H21A109.8C3TB—C4TB—C5TB120.0
C16—C21—H21B109.8C3TB—C4TB—H4TB120.0
C20—C21—H21B109.8C5TB—C4TB—H4TB120.0
H21A—C21—H21B108.3C4TB—C5TB—C6TB120.0
C27—C22—C23108.6 (5)C4TB—C5TB—H5TB120.0
C27—C22—P2114.9 (4)C6TB—C5TB—H5TB120.0
C23—C22—P2114.9 (4)C5TB—C6TB—C1TB120.0
C27—C22—H22A105.9C5TB—C6TB—H6TB120.0
C23—C22—H22A105.9C1TB—C6TB—H6TB120.0
P2—C22—H22A105.9C1TB—C7TB—H7TD109.5
C24—C23—C22110.1 (6)C1TB—C7TB—H7TE109.5
C24—C23—H23A109.6H7TD—C7TB—H7TE109.5
C22—C23—H23A109.6C1TB—C7TB—H7TF109.5
C24—C23—H23B109.6H7TD—C7TB—H7TF109.5
C22—C23—H23B109.6H7TE—C7TB—H7TF109.5
H23A—C23—H23B108.2
C1—Ru1—P1—C16166.5 (3)C10—P1—C16—C1768.9 (5)
C3—Ru1—P1—C1657.2 (3)Ru1—P1—C16—C17−60.3 (5)
C2—Ru1—P1—C16−70.3 (3)C21—C16—C17—C1862.4 (7)
P2—Ru1—P1—C16−115.0 (9)P1—C16—C17—C18−169.4 (4)
C1—Ru1—P1—C4−75.5 (3)C16—C17—C18—C19−57.9 (7)
C3—Ru1—P1—C4175.2 (3)C17—C18—C19—C2052.4 (8)
C2—Ru1—P1—C447.7 (3)C18—C19—C20—C21−51.7 (9)
P2—Ru1—P1—C43.0 (10)C17—C16—C21—C20−59.8 (7)
C1—Ru1—P1—C1043.0 (3)P1—C16—C21—C20173.0 (5)
C3—Ru1—P1—C10−66.3 (3)C19—C20—C21—C1655.4 (8)
C2—Ru1—P1—C10166.3 (3)C34—P2—C22—C2799.1 (5)
P2—Ru1—P1—C10121.6 (9)C28—P2—C22—C27−153.4 (4)
C1—Ru1—P2—C34−167.3 (3)Ru1—P2—C22—C27−31.1 (5)
C3—Ru1—P2—C34−58.0 (3)C34—P2—C22—C23−28.0 (5)
C2—Ru1—P2—C3469.5 (3)C28—P2—C22—C2379.6 (5)
P1—Ru1—P2—C34114.1 (9)Ru1—P2—C22—C23−158.2 (4)
C1—Ru1—P2—C2875.1 (3)C27—C22—C23—C2457.9 (7)
C3—Ru1—P2—C28−175.6 (3)P2—C22—C23—C24−172.0 (4)
C2—Ru1—P2—C28−48.1 (3)C22—C23—C24—C25−59.0 (8)
P1—Ru1—P2—C28−3.5 (10)C23—C24—C25—C2657.0 (8)
C1—Ru1—P2—C22−43.7 (3)C24—C25—C26—C27−55.6 (8)
C3—Ru1—P2—C2265.6 (3)C25—C26—C27—C2256.3 (7)
C2—Ru1—P2—C22−167.0 (3)C23—C22—C27—C26−56.9 (7)
P1—Ru1—P2—C22−122.3 (9)P2—C22—C27—C26173.0 (4)
C3—Ru1—C1—O1−7(12)C34—P2—C28—C33176.4 (5)
C2—Ru1—C1—O1173 (12)C22—P2—C28—C3367.8 (5)
P1—Ru1—C1—O1−99 (12)Ru1—P2—C28—C33−57.4 (5)
P2—Ru1—C1—O184 (12)C34—P2—C28—C2948.7 (5)
C1—Ru1—C2—O218 (11)C22—P2—C28—C29−59.9 (5)
C3—Ru1—C2—O2−162 (11)Ru1—P2—C28—C29174.9 (4)
P1—Ru1—C2—O2−70 (11)C33—C28—C29—C3056.1 (7)
P2—Ru1—C2—O2107 (11)P2—C28—C29—C30−174.4 (5)
C1—Ru1—C3—O36(5)C28—C29—C30—C31−58.2 (8)
C2—Ru1—C3—O3−174 (5)C29—C30—C31—C3257.0 (9)
P1—Ru1—C3—O396 (5)C30—C31—C32—C33−55.6 (9)
P2—Ru1—C3—O3−85 (5)C29—C28—C33—C32−54.3 (7)
C16—P1—C4—C5−177.6 (4)P2—C28—C33—C32174.3 (5)
C10—P1—C4—C5−69.4 (5)C31—C32—C33—C2855.6 (8)
Ru1—P1—C4—C555.8 (5)C28—P2—C34—C35−178.1 (4)
C16—P1—C4—C9−49.5 (5)C22—P2—C34—C35−69.1 (5)
C10—P1—C4—C958.7 (5)Ru1—P2—C34—C3560.0 (5)
Ru1—P1—C4—C9−176.1 (4)C28—P2—C34—C3956.6 (5)
C9—C4—C5—C653.4 (7)C22—P2—C34—C39165.6 (4)
P1—C4—C5—C6−175.2 (5)Ru1—P2—C34—C39−65.3 (5)
C4—C5—C6—C7−55.3 (8)C39—C34—C35—C36−60.5 (7)
C5—C6—C7—C856.8 (8)P2—C34—C35—C36172.2 (5)
C6—C7—C8—C9−58.1 (9)C34—C35—C36—C3757.5 (8)
C7—C8—C9—C457.7 (8)C35—C36—C37—C38−53.2 (8)
C5—C4—C9—C8−55.5 (8)C36—C37—C38—C3953.0 (8)
P1—C4—C9—C8175.4 (5)C37—C38—C39—C34−55.7 (8)
C16—P1—C10—C11−100.3 (4)C35—C34—C39—C3859.4 (7)
C4—P1—C10—C11152.2 (4)P2—C34—C39—C38−173.8 (4)
Ru1—P1—C10—C1130.0 (5)C7TA—C1TA—C2TA—C3TA−178.5 (9)
C16—P1—C10—C1527.4 (5)C6TA—C1TA—C2TA—C3TA0.0
C4—P1—C10—C15−80.0 (5)C1TA—C2TA—C3TA—C4TA0.0
Ru1—P1—C10—C15157.8 (4)C2TA—C3TA—C4TA—C5TA0.0
C15—C10—C11—C1257.3 (6)C3TA—C4TA—C5TA—C6TA0.0
P1—C10—C11—C12−171.9 (4)C4TA—C5TA—C6TA—C1TA0.0
C10—C11—C12—C13−56.8 (7)C7TA—C1TA—C6TA—C5TA178.5 (9)
C11—C12—C13—C1455.3 (7)C2TA—C1TA—C6TA—C5TA0.0
C12—C13—C14—C15−55.8 (7)C7TB—C1TB—C2TB—C3TB179.6 (11)
C13—C14—C15—C1058.6 (7)C6TB—C1TB—C2TB—C3TB0.0
C11—C10—C15—C14−58.6 (7)C1TB—C2TB—C3TB—C4TB0.0
P1—C10—C15—C14170.7 (4)C2TB—C3TB—C4TB—C5TB0.0
C4—P1—C16—C21−57.4 (5)C3TB—C4TB—C5TB—C6TB0.0
C10—P1—C16—C21−166.0 (5)C4TB—C5TB—C6TB—C1TB0.0
Ru1—P1—C16—C2164.9 (5)C7TB—C1TB—C6TB—C5TB−179.6 (11)
C4—P1—C16—C17177.4 (4)C2TB—C1TB—C6TB—C5TB0.0
Table 1
Selected geometric parameters (Å, °) top
Ru1—C11.903 (6)Ru1—P12.3777 (15)
Ru1—C31.915 (6)Ru1—P22.3780 (15)
Ru1—C21.919 (7)
P1—Ru1—P2176.22 (5)
references
References top

Berger, D. & Imhof, W. (1999). Chem. Commun. pp. 1457–1458.

Chaudret, B. & Poilblanc, R. (1985). Organometallics, 4, 1722–1726.

Dönnecke, D. & Imhof, W. (2003). Tetrahedron, 59, 8499–8507.

Dunne, J. P., Blazina, D., Aiken, S., Carteret, H. A., Duckett, S. B., Jones, J. A., Poli, R. & Whitwood, A. C. (2004). Dalton Trans. pp. 3616–3628.

Nonius (1998). COLLECT, Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Siemens (1990). XP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Song, L. & Trogler, W. C. (1992). J. Am. Chem. Soc. 114, 3355–3361.