Carbonyl(η⁵-penta­methyl­cyclo­penta­dienyl)(triflato-O)(triiso­propyl­phosphine-P)­ruthenium(II)

The title complex, [RuCp*(OSO₂CF₃){P(ⁱPr)₃}(CO)] or [Ru(CF₃O₃S)(C₁₀H₁₅)(C₉H₂₁P)(CO)], consists of an Ru atom coordinated by an inner sphere tri­fluoro­methane­sulfonate, a carbonyl, and a triiso­propyl­phosphine in a `three-legged stool' fashion.

Key indicators

• Single-crystal X-ray study
• T = 128 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.038
• wR factor = 0.089
• Data-to-parameter ratio = 14.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5875


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

Monocyclopentadienyl complexes of group VIII transition metals are of interest because of their participation in a variety of important stoichiometric and catalytic processes. Especially of interest are those group VIII complexes with highly labile substituents, such as trifluoromethanesulfonate groups, since such groups can easily generate a vacant coordination site during chemical reactions.

In the compound studied, the Ru atom is coordinated in a `three-legged piano-stool' fashion by one O atom of the trifluoromethanesulfonate, a carbonyl, a triisopropylphosphine, and a pentamethylcyclopentadienyl (Cp*). An examination of the Cambridge Structural Database (CSD; Allen & Kennard, 1993) reveals that even though there exist numerous cationic species containing Cp or Cp*, a P(ⁱPr)₃ and a carbonyl ligand; there are only four neutral species. The distance between the Ru atom and the coordinated O atom of the trifluoromethanesulfonate [2.195 (3) Å] is longer than that of most Ru—O distances in similar Ru–trifluoromethanesulfonate compounds [2.125 (5)–2.177 (4) Å; Gemel et al., 1997; Svetlanova-Larsen et al., 1996; Burns & Hubbard, 1994; Ontko et al., 1998]; only one of six compounds had a longer distance [2.277 (2) Å; Mauthner et al., 1997]. The Ru—P bond distance [2.395 (1) Å] is comparable with that found in similar Cp*–Ru–carbonyl–triisopropylphosphine complexes (typically 2.39 Å; Campion et al., 1988; Bernad et al., 2000). The Ru—C_Cp* bond distances [2.203 (4)–2.287 (4) Å] are within the expected range for half-sandwich Ru^II compounds (Johnson et al., 1995).

S2. Experimental

The title compound was synthesized from RuCp*(P(ⁱPr)₃)(OSO₂CF₃) stirred under an atmosphere of CO. Crystals were grown by diffusion of pentane into a deuterobenzene solution.

S3. Refinement

H atoms were refined as riding, with C—H distances of 0.98 or 1.00 Å.

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1995); molecular graphics: TEXSAN (Molecular Structure Corporation, 1992); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The molecular structure of the title compound shown with 50% probability displacement ellipsoids.

(I)

Crystal data

[Ru(CF3O3S)(C10H15)(C9H21P)(CO)]	F(000) = 1184
Mr = 573.60	Dx = 1.547 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.056 (1) Å	Cell parameters from 4749 reflections
b = 9.1258 (5) Å	θ = 1.7–24.7°
c = 17.005 (1) Å	µ = 0.83 mm^−1
β = 98.796 (1)°	T = 128 K
V = 2462.3 (3) Å^3	Tablet, orange
Z = 4	0.27 × 0.13 × 0.08 mm

Data collection

SMART CCD diffractometer	4036 independent reflections
Radiation source: fine-focus sealed tube	3238 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω scans	θmax = 24.7°, θmin = 2.4°
Absorption correction: empirical (using intensity measurements) (Blessing, 1995)	h = −6→18
Tmin = 0.81, Tmax = 0.91	k = −10→10
10547 measured reflections	l = −19→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.089	H-atom parameters constrained
S = 1.05
4035 reflections	(Δ/σ)max = −0.042
280 parameters	Δρmax = 0.70 e Å^−3
0 restraints	Δρmin = −0.71 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 on F² for ALL reflections except for 1 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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	0.80665 (2)	0.14945 (3)	0.35101 (2)	0.01478 (12)
S1	0.75355 (6)	−0.03166 (11)	0.18512 (6)	0.0195 (2)
P1	0.66998 (6)	0.23037 (11)	0.37238 (6)	0.0153 (2)
F1	0.7381 (2)	−0.3146 (3)	0.2030 (2)	0.0488 (8)
F2	0.6913 (2)	−0.2357 (3)	0.08565 (15)	0.0418 (7)
F3	0.6200 (2)	−0.2004 (3)	0.1809 (2)	0.0447 (7)
O1	0.8313 (2)	0.3853 (3)	0.2333 (2)	0.0355 (8)
O2	0.7418 (2)	−0.0146 (3)	0.26915 (15)	0.0187 (6)
O3	0.7069 (2)	0.0721 (3)	0.1325 (2)	0.0276 (7)
O4	0.8379 (2)	−0.0609 (3)	0.1728 (2)	0.0309 (7)
C1	0.8128 (3)	0.2949 (5)	0.2753 (2)	0.0227 (9)
C2	0.6732 (3)	0.3967 (4)	0.4354 (2)	0.0224 (10)
H2	0.7011 (3)	0.3654 (4)	0.4894 (2)	0.027*
C3	0.5857 (3)	0.4568 (5)	0.4474 (3)	0.0315 (11)
H3A	0.5512 (3)	0.3765 (5)	0.4630 (3)	0.038*
H3B	0.5578 (3)	0.5003 (5)	0.3976 (3)	0.038*
H3C	0.5930 (3)	0.5316 (5)	0.4893 (3)	0.038*
C4	0.7275 (3)	0.5198 (5)	0.4112 (3)	0.0328 (11)
H4A	0.7826 (3)	0.4807 (5)	0.4037 (3)	0.039*
H4B	0.7352 (3)	0.5947 (5)	0.4530 (3)	0.039*
H4C	0.6999 (3)	0.5635 (5)	0.3613 (3)	0.039*
C5	0.5909 (2)	0.2789 (4)	0.2842 (2)	0.0192 (9)
H5	0.5470 (2)	0.3387 (4)	0.3053 (2)	0.023*
C6	0.6269 (3)	0.3780 (5)	0.2245 (2)	0.0251 (10)
H6A	0.6572 (3)	0.4602 (5)	0.2528 (2)	0.030*
H6B	0.5807 (3)	0.4157 (5)	0.1853 (2)	0.030*
H6C	0.6657 (3)	0.3214 (5)	0.1971 (2)	0.030*
C7	0.5437 (3)	0.1512 (5)	0.2393 (2)	0.0261 (10)
H7A	0.5204 (3)	0.0877 (5)	0.2770 (2)	0.031*
H7B	0.5826 (3)	0.0948 (5)	0.2120 (2)	0.031*
H7C	0.4977 (3)	0.1894 (5)	0.2001 (2)	0.031*
C8	0.6072 (3)	0.0981 (5)	0.4242 (2)	0.0240 (10)
H8	0.5464 (3)	0.1243 (5)	0.4084 (2)	0.029*
C9	0.6256 (3)	0.1052 (5)	0.5148 (3)	0.0320 (11)
H9A	0.6186 (3)	0.2062 (5)	0.5323 (3)	0.038*
H9B	0.6835 (3)	0.0730 (5)	0.5329 (3)	0.038*
H9C	0.5863 (3)	0.0411 (5)	0.5373 (3)	0.038*
C10	0.6178 (3)	−0.0594 (5)	0.3964 (3)	0.0277 (10)
H10A	0.6059 (3)	−0.0634 (5)	0.3382 (3)	0.033*
H10B	0.5785 (3)	−0.1236 (5)	0.4189 (3)	0.033*
H10C	0.6757 (3)	−0.0919 (5)	0.4144 (3)	0.033*
C11	0.6981 (3)	−0.2056 (5)	0.1631 (2)	0.0266 (10)
C12	0.8806 (2)	0.1778 (5)	0.4713 (2)	0.0222 (10)
C13	0.9300 (3)	0.2246 (5)	0.4117 (2)	0.0226 (9)
C14	0.9438 (3)	0.0991 (5)	0.3642 (2)	0.0242 (10)
C15	0.9039 (3)	−0.0229 (5)	0.3950 (2)	0.0238 (10)
C16	0.8661 (2)	0.0229 (5)	0.4613 (2)	0.0206 (9)
C17	0.8645 (3)	0.2671 (5)	0.5420 (2)	0.0273 (10)
H17A	0.8794 (3)	0.3696 (5)	0.5342 (2)	0.033*
H17B	0.8988 (3)	0.2290 (5)	0.5903 (2)	0.033*
H17C	0.8047 (3)	0.2607 (5)	0.5474 (2)	0.033*
C18	0.9692 (3)	0.3730 (5)	0.4074 (3)	0.0323 (11)
H18A	0.9490 (3)	0.4384 (5)	0.4462 (3)	0.039*
H18B	0.9534 (3)	0.4133 (5)	0.3538 (3)	0.039*
H18C	1.0306 (3)	0.3643 (5)	0.4195 (3)	0.039*
C19	0.9969 (3)	0.0968 (6)	0.2980 (3)	0.0377 (12)
H19A	1.0164 (3)	0.1962 (6)	0.2889 (3)	0.045*
H19B	0.9630 (3)	0.0600 (6)	0.2491 (3)	0.045*
H19C	1.0456 (3)	0.0325 (6)	0.3130 (3)	0.045*
C20	0.9009 (3)	−0.1770 (5)	0.3636 (3)	0.0335 (11)
H20A	0.8694 (3)	−0.2390 (5)	0.3959 (3)	0.040*
H20B	0.9584 (3)	−0.2148 (5)	0.3663 (3)	0.040*
H20C	0.8728 (3)	−0.1778 (5)	0.3082 (3)	0.040*
C21	0.8349 (3)	−0.0796 (5)	0.5192 (3)	0.0322 (11)
H21A	0.8114 (3)	−0.0229 (5)	0.5596 (3)	0.039*
H21B	0.8818 (3)	−0.1398 (5)	0.5451 (3)	0.039*
H21C	0.7911 (3)	−0.1432 (5)	0.4909 (3)	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.0141 (2)	0.0187 (2)	0.0119 (2)	0.00015 (14)	0.00332 (13)	−0.00071 (13)
S1	0.0236 (6)	0.0203 (5)	0.0154 (5)	−0.0016 (4)	0.0059 (4)	−0.0017 (4)
P1	0.0160 (5)	0.0185 (6)	0.0118 (5)	0.0008 (4)	0.0035 (4)	0.0001 (4)
F1	0.068 (2)	0.0222 (15)	0.054 (2)	−0.0011 (14)	0.003 (2)	0.0083 (13)
F2	0.060 (2)	0.038 (2)	0.0276 (15)	−0.0072 (14)	0.0083 (13)	−0.0211 (12)
F3	0.033 (2)	0.050 (2)	0.055 (2)	−0.0173 (14)	0.0197 (14)	−0.0232 (15)
O1	0.034 (2)	0.038 (2)	0.036 (2)	−0.0055 (15)	0.011 (2)	0.015 (2)
O2	0.022 (2)	0.023 (2)	0.0124 (13)	−0.0021 (12)	0.0040 (12)	−0.0017 (11)
O3	0.043 (2)	0.025 (2)	0.0155 (15)	0.0033 (14)	0.0052 (14)	0.0013 (12)
O4	0.026 (2)	0.042 (2)	0.028 (2)	−0.0046 (15)	0.0137 (14)	−0.0050 (14)
C1	0.018 (2)	0.026 (2)	0.024 (2)	0.001 (2)	0.003 (2)	−0.003 (2)
C2	0.028 (2)	0.025 (2)	0.015 (2)	0.003 (2)	0.002 (2)	−0.005 (2)
C3	0.030 (3)	0.036 (3)	0.028 (2)	0.007 (2)	0.003 (2)	−0.012 (2)
C4	0.050 (3)	0.021 (2)	0.028 (2)	−0.005 (2)	0.008 (2)	−0.012 (2)
C5	0.016 (2)	0.025 (2)	0.016 (2)	0.004 (2)	−0.001 (2)	−0.001 (2)
C6	0.028 (2)	0.029 (3)	0.018 (2)	0.009 (2)	0.001 (2)	0.006 (2)
C7	0.026 (2)	0.028 (2)	0.022 (2)	−0.001 (2)	−0.002 (2)	−0.003 (2)
C8	0.021 (2)	0.032 (2)	0.021 (2)	0.001 (2)	0.007 (2)	0.006 (2)
C9	0.034 (3)	0.039 (3)	0.024 (2)	−0.004 (2)	0.008 (2)	0.005 (2)
C10	0.028 (3)	0.029 (3)	0.027 (2)	−0.007 (2)	0.007 (2)	0.004 (2)
C11	0.035 (3)	0.022 (2)	0.024 (2)	−0.002 (2)	0.008 (2)	−0.005 (2)
C12	0.014 (2)	0.035 (3)	0.017 (2)	0.003 (2)	−0.001 (2)	−0.001 (2)
C13	0.018 (2)	0.028 (2)	0.021 (2)	−0.002 (2)	0.003 (2)	−0.002 (2)
C14	0.015 (2)	0.035 (3)	0.022 (2)	0.000 (2)	0.002 (2)	−0.004 (2)
C15	0.021 (2)	0.027 (2)	0.021 (2)	0.008 (2)	−0.005 (2)	0.000 (2)
C16	0.018 (2)	0.026 (2)	0.016 (2)	0.004 (2)	−0.002 (2)	0.003 (2)
C17	0.022 (2)	0.041 (3)	0.018 (2)	0.000 (2)	0.001 (2)	−0.010 (2)
C18	0.024 (3)	0.041 (3)	0.031 (3)	−0.012 (2)	0.003 (2)	−0.009 (2)
C19	0.020 (3)	0.062 (3)	0.033 (3)	−0.002 (2)	0.010 (2)	−0.012 (2)
C20	0.033 (3)	0.028 (3)	0.039 (3)	0.010 (2)	0.000 (2)	−0.001 (2)
C21	0.035 (3)	0.035 (3)	0.024 (2)	0.002 (2)	−0.002 (2)	0.010 (2)

Geometric parameters (Å, º)

Ru1—C1	1.862 (4)	C7—H7C	0.98
Ru1—O2	2.195 (3)	C8—C9	1.525 (6)
Ru1—C13	2.198 (4)	C8—C10	1.530 (6)
Ru1—C12	2.218 (4)	C8—H8	1.00
Ru1—C14	2.227 (4)	C9—H9A	0.98
Ru1—C15	2.261 (4)	C9—H9B	0.98
Ru1—C16	2.284 (4)	C9—H9C	0.98
Ru1—P1	2.3952 (11)	C10—H10A	0.98
S1—O4	1.427 (3)	C10—H10B	0.98
S1—O3	1.433 (3)	C10—H10C	0.98
S1—O2	1.478 (3)	C12—C16	1.439 (6)
S1—C11	1.830 (4)	C12—C13	1.443 (6)
P1—C2	1.854 (4)	C12—C17	1.507 (6)
P1—C5	1.864 (4)	C13—C14	1.438 (6)
P1—C8	1.877 (4)	C13—C18	1.500 (6)
F1—C11	1.315 (5)	C14—C15	1.423 (6)
F2—C11	1.334 (5)	C14—C19	1.513 (6)
F3—C11	1.334 (5)	C15—C16	1.422 (6)
O1—C1	1.159 (5)	C15—C20	1.503 (6)
C2—C4	1.516 (6)	C16—C21	1.499 (6)
C2—C3	1.551 (6)	C17—H17A	0.98
C2—H2	1.00	C17—H17B	0.98
C3—H3A	0.98	C17—H17C	0.98
C3—H3B	0.98	C18—H18A	0.98
C3—H3C	0.98	C18—H18B	0.98
C4—H4A	0.98	C18—H18C	0.98
C4—H4B	0.98	C19—H19A	0.98
C4—H4C	0.98	C19—H19B	0.98
C5—C7	1.529 (5)	C19—H19C	0.98
C5—C6	1.538 (6)	C20—H20A	0.98
C5—H5	1.00	C20—H20B	0.98
C6—H6A	0.98	C20—H20C	0.98
C6—H6B	0.98	C21—H21A	0.98
C6—H6C	0.98	C21—H21B	0.98
C7—H7A	0.98	C21—H21C	0.98
C7—H7B	0.98
C1—Ru1—O2	96.76 (14)	C9—C8—H8	107.0
C1—Ru1—C13	87.9 (2)	C10—C8—H8	107.0
O2—Ru1—C13	144.71 (13)	P1—C8—H8	106.9
C1—Ru1—C12	118.5 (2)	C8—C9—H9A	109.5
O2—Ru1—C12	143.07 (13)	C8—C9—H9B	109.5
C13—Ru1—C12	38.15 (15)	H9A—C9—H9B	109.5
C1—Ru1—C14	93.5 (2)	C8—C9—H9C	109.5
O2—Ru1—C14	106.80 (13)	H9A—C9—H9C	109.5
C13—Ru1—C14	37.92 (15)	H9B—C9—H9C	109.5
C12—Ru1—C14	63.21 (15)	C8—C10—H10A	109.5
C1—Ru1—C15	128.1 (2)	C8—C10—H10B	109.5
O2—Ru1—C15	88.39 (13)	H10A—C10—H10B	109.5
C13—Ru1—C15	62.3 (2)	C8—C10—H10C	109.5
C12—Ru1—C15	62.01 (15)	H10A—C10—H10C	109.5
C14—Ru1—C15	37.0 (2)	H10B—C10—H10C	109.5
C1—Ru1—C16	150.3 (2)	F1—C11—F3	108.2 (4)
O2—Ru1—C16	105.89 (13)	F1—C11—F2	108.2 (4)
C13—Ru1—C16	62.52 (15)	F3—C11—F2	107.0 (4)
C12—Ru1—C16	37.24 (15)	F1—C11—S1	111.5 (3)
C14—Ru1—C16	62.0 (2)	F3—C11—S1	111.6 (3)
C15—Ru1—C16	36.47 (14)	F2—C11—S1	110.2 (3)
C1—Ru1—P1	91.82 (13)	C16—C12—C13	107.7 (4)
O2—Ru1—P1	87.12 (7)	C16—C12—C17	125.5 (4)
C13—Ru1—P1	127.81 (11)	C13—C12—C17	125.5 (4)
C12—Ru1—P1	101.41 (11)	C16—C12—Ru1	73.9 (2)
C14—Ru1—P1	164.38 (11)	C13—C12—Ru1	70.2 (2)
C15—Ru1—P1	140.04 (11)	C17—C12—Ru1	131.7 (3)
C16—Ru1—P1	108.00 (11)	C14—C13—C12	107.9 (4)
O4—S1—O3	116.6 (2)	C14—C13—C18	126.1 (4)
O4—S1—O2	115.2 (2)	C12—C13—C18	125.5 (4)
O3—S1—O2	113.8 (2)	C14—C13—Ru1	72.1 (2)
O4—S1—C11	104.5 (2)	C12—C13—Ru1	71.7 (2)
O3—S1—C11	104.7 (2)	C18—C13—Ru1	127.8 (3)
O2—S1—C11	99.1 (2)	C15—C14—C13	107.4 (4)
C2—P1—C5	103.0 (2)	C15—C14—C19	126.8 (4)
C2—P1—C8	103.0 (2)	C13—C14—C19	125.6 (4)
C5—P1—C8	100.4 (2)	C15—C14—Ru1	72.8 (2)
C2—P1—Ru1	113.23 (14)	C13—C14—Ru1	69.9 (2)
C5—P1—Ru1	118.58 (13)	C19—C14—Ru1	126.1 (3)
C8—P1—Ru1	116.33 (14)	C14—C15—C16	109.4 (4)
S1—O2—Ru1	124.5 (2)	C14—C15—C20	126.4 (4)
O1—C1—Ru1	168.2 (4)	C16—C15—C20	124.2 (4)
C4—C2—C3	110.1 (4)	C14—C15—Ru1	70.2 (2)
C4—C2—P1	114.6 (3)	C16—C15—Ru1	72.6 (2)
C3—C2—P1	114.8 (3)	C20—C15—Ru1	123.4 (3)
C4—C2—H2	105.4	C15—C16—C12	107.5 (4)
C3—C2—H2	105.4	C15—C16—C21	124.3 (4)
P1—C2—H2	105.4	C12—C16—C21	126.9 (4)
C2—C3—H3A	109.5	C15—C16—Ru1	70.9 (2)
C2—C3—H3B	109.5	C12—C16—Ru1	68.9 (2)
H3A—C3—H3B	109.5	C21—C16—Ru1	135.7 (3)
C2—C3—H3C	109.5	C12—C17—H17A	109.5
H3A—C3—H3C	109.5	C12—C17—H17B	109.5
H3B—C3—H3C	109.5	H17A—C17—H17B	109.5
C2—C4—H4A	109.5	C12—C17—H17C	109.5
C2—C4—H4B	109.5	H17A—C17—H17C	109.5
H4A—C4—H4B	109.5	H17B—C17—H17C	109.5
C2—C4—H4C	109.5	C13—C18—H18A	109.5
H4A—C4—H4C	109.5	C13—C18—H18B	109.5
H4B—C4—H4C	109.5	H18A—C18—H18B	109.5
C7—C5—C6	109.0 (3)	C13—C18—H18C	109.5
C7—C5—P1	116.4 (3)	H18A—C18—H18C	109.5
C6—C5—P1	113.1 (3)	H18B—C18—H18C	109.5
C7—C5—H5	105.8	C14—C19—H19A	109.5
C6—C5—H5	105.8	C14—C19—H19B	109.5
P1—C5—H5	105.8	H19A—C19—H19B	109.5
C5—C6—H6A	109.5	C14—C19—H19C	109.5
C5—C6—H6B	109.5	H19A—C19—H19C	109.5
H6A—C6—H6B	109.5	H19B—C19—H19C	109.5
C5—C6—H6C	109.5	C15—C20—H20A	109.5
H6A—C6—H6C	109.5	C15—C20—H20B	109.5
H6B—C6—H6C	109.5	H20A—C20—H20B	109.5
C5—C7—H7A	109.5	C15—C20—H20C	109.5
C5—C7—H7B	109.5	H20A—C20—H20C	109.5
H7A—C7—H7B	109.5	H20B—C20—H20C	109.5
C5—C7—H7C	109.5	C16—C21—H21A	109.5
H7A—C7—H7C	109.5	C16—C21—H21B	109.5
H7B—C7—H7C	109.5	H21A—C21—H21B	109.5
C9—C8—C10	109.8 (4)	C16—C21—H21C	109.5
C9—C8—P1	114.3 (3)	H21A—C21—H21C	109.5
C10—C8—P1	111.5 (3)	H21B—C21—H21C	109.5
C1—Ru1—P1—C2	−77.6 (2)	C15—Ru1—C13—C12	−79.1 (3)
O2—Ru1—P1—C2	−174.3 (2)	C16—Ru1—C13—C12	−37.8 (2)
C13—Ru1—P1—C2	11.1 (2)	P1—Ru1—C13—C12	54.4 (3)
C12—Ru1—P1—C2	41.9 (2)	C1—Ru1—C13—C18	23.9 (4)
C14—Ru1—P1—C2	32.2 (5)	O2—Ru1—C13—C18	122.7 (3)
C15—Ru1—P1—C2	101.6 (2)	C12—Ru1—C13—C18	−121.1 (5)
C16—Ru1—P1—C2	79.9 (2)	C14—Ru1—C13—C18	122.3 (5)
C1—Ru1—P1—C5	43.3 (2)	C15—Ru1—C13—C18	159.8 (4)
O2—Ru1—P1—C5	−53.4 (2)	C16—Ru1—C13—C18	−158.9 (4)
C13—Ru1—P1—C5	132.0 (2)	P1—Ru1—C13—C18	−66.8 (4)
C12—Ru1—P1—C5	162.8 (2)	C12—C13—C14—C15	−0.5 (5)
C14—Ru1—P1—C5	153.1 (5)	C18—C13—C14—C15	172.1 (4)
C15—Ru1—P1—C5	−137.5 (2)	Ru1—C13—C14—C15	−63.6 (3)
C16—Ru1—P1—C5	−159.2 (2)	C12—C13—C14—C19	−176.2 (4)
C1—Ru1—P1—C8	163.3 (2)	C18—C13—C14—C19	−3.6 (7)
O2—Ru1—P1—C8	66.6 (2)	Ru1—C13—C14—C19	120.6 (4)
C13—Ru1—P1—C8	−108.0 (2)	C12—C13—C14—Ru1	63.2 (3)
C12—Ru1—P1—C8	−77.2 (2)	C18—C13—C14—Ru1	−124.2 (4)
C14—Ru1—P1—C8	−86.9 (5)	C1—Ru1—C14—C15	−161.4 (3)
C15—Ru1—P1—C8	−17.5 (2)	O2—Ru1—C14—C15	−63.3 (2)
C16—Ru1—P1—C8	−39.2 (2)	C13—Ru1—C14—C15	116.5 (3)
O4—S1—O2—Ru1	58.5 (2)	C12—Ru1—C14—C15	78.3 (3)
O3—S1—O2—Ru1	−80.0 (2)	C16—Ru1—C14—C15	36.1 (2)
C11—S1—O2—Ru1	169.4 (2)	P1—Ru1—C14—C15	89.0 (5)
C1—Ru1—O2—S1	32.7 (2)	C1—Ru1—C14—C13	82.1 (3)
C13—Ru1—O2—S1	−63.2 (3)	O2—Ru1—C14—C13	−179.8 (2)
C12—Ru1—O2—S1	−130.5 (2)	C12—Ru1—C14—C13	−38.2 (2)
C14—Ru1—O2—S1	−63.0 (2)	C15—Ru1—C14—C13	−116.5 (3)
C15—Ru1—O2—S1	−95.5 (2)	C16—Ru1—C14—C13	−80.4 (3)
C16—Ru1—O2—S1	−127.9 (2)	P1—Ru1—C14—C13	−27.5 (6)
P1—Ru1—O2—S1	124.2 (2)	C1—Ru1—C14—C19	−38.0 (4)
O2—Ru1—C1—O1	−126.5 (18)	O2—Ru1—C14—C19	60.1 (4)
C13—Ru1—C1—O1	18.4 (18)	C13—Ru1—C14—C19	−120.1 (5)
C12—Ru1—C1—O1	42.1 (19)	C12—Ru1—C14—C19	−158.3 (4)
C14—Ru1—C1—O1	−19.1 (18)	C15—Ru1—C14—C19	123.4 (5)
C15—Ru1—C1—O1	−33.3 (19)	C16—Ru1—C14—C19	159.5 (4)
C16—Ru1—C1—O1	13 (2)	P1—Ru1—C14—C19	−147.6 (3)
P1—Ru1—C1—O1	146.2 (18)	C13—C14—C15—C16	−0.7 (5)
C5—P1—C2—C4	−81.0 (3)	C19—C14—C15—C16	175.0 (4)
C8—P1—C2—C4	174.9 (3)	Ru1—C14—C15—C16	−62.4 (3)
Ru1—P1—C2—C4	48.4 (3)	C13—C14—C15—C20	179.2 (4)
C5—P1—C2—C3	48.0 (3)	C19—C14—C15—C20	−5.1 (7)
C8—P1—C2—C3	−56.2 (3)	Ru1—C14—C15—C20	117.5 (4)
Ru1—P1—C2—C3	177.3 (3)	C13—C14—C15—Ru1	61.8 (3)
C2—P1—C5—C7	−153.4 (3)	C19—C14—C15—Ru1	−122.6 (4)
C8—P1—C5—C7	−47.3 (3)	C1—Ru1—C15—C14	23.9 (3)
Ru1—P1—C5—C7	80.6 (3)	O2—Ru1—C15—C14	121.2 (2)
C2—P1—C5—C6	79.1 (3)	C13—Ru1—C15—C14	−38.4 (2)
C8—P1—C5—C6	−174.7 (3)	C12—Ru1—C15—C14	−81.8 (3)
Ru1—P1—C5—C6	−46.9 (3)	C16—Ru1—C15—C14	−118.9 (4)
C2—P1—C8—C9	−38.5 (4)	P1—Ru1—C15—C14	−155.2 (2)
C5—P1—C8—C9	−144.6 (3)	C1—Ru1—C15—C16	142.7 (3)
Ru1—P1—C8—C9	86.0 (3)	O2—Ru1—C15—C16	−119.9 (2)
C2—P1—C8—C10	−163.7 (3)	C13—Ru1—C15—C16	80.5 (3)
C5—P1—C8—C10	90.2 (3)	C12—Ru1—C15—C16	37.1 (2)
Ru1—P1—C8—C10	−39.2 (3)	C14—Ru1—C15—C16	118.9 (4)
O4—S1—C11—F1	51.8 (3)	C16—Ru1—C15—C16	0.000 (1)
O3—S1—C11—F1	174.9 (3)	P1—Ru1—C15—C16	−36.3 (3)
O2—S1—C11—F1	−67.4 (3)	C1—Ru1—C15—C20	−97.4 (4)
O4—S1—C11—F3	172.8 (3)	O2—Ru1—C15—C20	0.0 (4)
O3—S1—C11—F3	−64.0 (3)	C13—Ru1—C15—C20	−159.6 (4)
O2—S1—C11—F3	53.7 (3)	C12—Ru1—C15—C20	157.0 (4)
O4—S1—C11—F2	−68.4 (3)	C14—Ru1—C15—C20	−121.2 (5)
O3—S1—C11—F2	54.7 (3)	C16—Ru1—C15—C20	119.9 (5)
O2—S1—C11—F2	172.4 (3)	P1—Ru1—C15—C20	83.6 (4)
C1—Ru1—C12—C16	−156.8 (2)	C14—C15—C16—C12	1.5 (5)
O2—Ru1—C12—C16	4.2 (3)	C20—C15—C16—C12	−178.4 (4)
C13—Ru1—C12—C16	−116.1 (3)	Ru1—C15—C16—C12	−59.4 (3)
C14—Ru1—C12—C16	−78.1 (3)	C14—C15—C16—C21	−166.3 (4)
C15—Ru1—C12—C16	−36.3 (2)	C20—C15—C16—C21	13.8 (6)
P1—Ru1—C12—C16	104.8 (2)	Ru1—C15—C16—C21	132.8 (4)
C1—Ru1—C12—C13	−40.6 (3)	C14—C15—C16—Ru1	60.9 (3)
O2—Ru1—C12—C13	120.4 (3)	C20—C15—C16—Ru1	−119.0 (4)
C14—Ru1—C12—C13	38.0 (2)	C13—C12—C16—C15	−1.8 (4)
C15—Ru1—C12—C13	79.8 (3)	C17—C12—C16—C15	−169.2 (4)
C16—Ru1—C12—C13	116.1 (3)	Ru1—C12—C16—C15	60.7 (3)
P1—Ru1—C12—C13	−139.1 (2)	C13—C12—C16—C21	165.6 (4)
C1—Ru1—C12—C17	79.7 (4)	C17—C12—C16—C21	−1.8 (7)
O2—Ru1—C12—C17	−119.3 (4)	Ru1—C12—C16—C21	−132.0 (4)
C13—Ru1—C12—C17	120.3 (5)	C13—C12—C16—Ru1	−62.4 (3)
C14—Ru1—C12—C17	158.3 (5)	C17—C12—C16—Ru1	130.2 (4)
C15—Ru1—C12—C17	−159.9 (5)	C1—Ru1—C16—C15	−74.0 (4)
C16—Ru1—C12—C17	−123.6 (5)	O2—Ru1—C16—C15	64.3 (3)
P1—Ru1—C12—C17	−18.8 (4)	C13—Ru1—C16—C15	−79.7 (3)
C16—C12—C13—C14	1.4 (4)	C12—Ru1—C16—C15	−118.4 (4)
C17—C12—C13—C14	168.8 (4)	C14—Ru1—C16—C15	−36.6 (2)
Ru1—C12—C13—C14	−63.5 (3)	P1—Ru1—C16—C15	156.4 (2)
C16—C12—C13—C18	−171.3 (4)	C1—Ru1—C16—C12	44.4 (4)
C17—C12—C13—C18	−3.8 (7)	O2—Ru1—C16—C12	−177.4 (2)
Ru1—C12—C13—C18	123.9 (4)	C13—Ru1—C16—C12	38.7 (2)
C16—C12—C13—Ru1	64.9 (3)	C14—Ru1—C16—C12	81.8 (3)
C17—C12—C13—Ru1	−127.7 (4)	C15—Ru1—C16—C12	118.4 (4)
C1—Ru1—C13—C14	−98.4 (3)	P1—Ru1—C16—C12	−85.2 (2)
O2—Ru1—C13—C14	0.4 (4)	C1—Ru1—C16—C21	166.0 (4)
C12—Ru1—C13—C14	116.6 (4)	O2—Ru1—C16—C21	−55.7 (4)
C15—Ru1—C13—C14	37.4 (2)	C13—Ru1—C16—C21	160.3 (5)
C16—Ru1—C13—C14	78.8 (3)	C12—Ru1—C16—C21	121.7 (5)
P1—Ru1—C13—C14	170.9 (2)	C14—Ru1—C16—C21	−156.6 (5)
C1—Ru1—C13—C12	145.1 (3)	C15—Ru1—C16—C21	−120.0 (5)
O2—Ru1—C13—C12	−116.2 (3)	P1—Ru1—C16—C21	36.5 (4)
C14—Ru1—C13—C12	−116.6 (4)