(η5-Cyclo­penta­dien­yl)(propionitrile-κN)bis­(triphenyl­phosphine-κP)ruthenium(II) trifluoro­methane­sulfonate

Mauthner, K.; Kirchner, K.; Mereiter, K.

doi:10.1107/S1600536809038720

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1267

https://doi.org/10.1107/S1600536809038720

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(η⁵-Cyclopentadienyl)(propionitrile-κN)bis(triphenylphosphine-κP)ruthenium(II) trifluoromethanesulfonate

Klaus Mauthner,^a Karl Kirchner ^a and Kurt Mereiter ^b ^*

^aInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, A-1060 Vienna, Austria, and ^bInstitute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna, Austria
^*Correspondence e-mail: kurt.mereiter@tuwien.ac.at

(Received 10 September 2009; accepted 24 September 2009; online 3 October 2009)

The title compound, [Ru(C₅H₅)(C₃H₅N)(C₁₈H₁₅P)₂]CF₃SO₃, forms yellow crystals with a distinctly hemimorphic habit. It contains a half-sandwich complex of ruthenium with a three-legged piano-stool geometry, with Ru—P = 2.3585 (4) and 2.3312 (4) Å, and Ru—N = 2.0422 (15) Å as the legs. The CF₃SO₃⁻ anion is anchored in the crystal lattice by C—H⋯O and C—H⋯F hydrogen bonds, with C⋯F,O distances starting at 3.125 (2) Å.

Related literature

For the application of nitrile-substituted ruthenium–cyclopentadienyl complexes in catalysis, see: Trost et al. (2001 ). For the synthesis, chemistry and crystal structures of related ruthenium–cyclopentadienyl complexes, see: Carreón et al. (1997 ); Cordiner et al. (2003 ); Mauthner et al. (1999 ); Rüba et al. (1999 , 2002 ); Bruce et al. (1982 ).

Experimental

Crystal data

[Ru(C₅H₅)(C₃H₅N)(C₁₈H₁₅P)₂]CF₃SO₃
M_r = 894.85
Monoclinic, P 2₁
a = 9.9991 (4) Å
b = 17.2172 (7) Å
c = 11.4605 (5) Å
β = 92.126 (1)°
V = 1971.64 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 123 K
0.31 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.79, T_max = 0.89
29537 measured reflections
11391 independent reflections
11056 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.061
S = 1.02
11391 reflections
505 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 5488 Friedel pairs
Flack parameter: −0.038 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯F1	0.95	2.49	3.125 (2)	125
C3—H3⋯O1ⁱ	0.95	2.50	3.154 (3)	126
C7—H7A⋯O3	0.99	2.43	3.346 (3)	153
C28—H28⋯O1ⁱ	0.95	2.56	3.328 (2)	138
C44—H44⋯O2	0.95	2.58	3.209 (2)	124
Symmetry code: (i) x, y, z+1.

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT, SADABS and XPREP (Bruker, 2003); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809038720/ez2188sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809038720/ez2188Isup2.hkl

checkCIF report

Comment top

Half-sandwich complexes based on the cationic fragment [CpRu]⁺ (Cp = cyclopentadienyl) and complemented by a combination of stabilizing phosphine and labile nitrile ligands are of interest as catalysts in organic chemistry for a variety of useful transformations of unsaturated systems, like C—C bond forming reactions, isomerizations, or C—H activations (Trost et al., 2001). In the context of our research in this area (Rüba et al., 1999, 2002; Mauthner et al., 1999) the title compound was synthesized from [CpRu(PPh₃)₂Cl] (Ph = phenyl) by halide abstraction with AgCF₃SO₃ in the presence of propionitrile. As an unconventional but efficient method, technical nitromethane was used as the reaction solvent because it provides good solubility of the reactants, already contains the propionitrile needed for the formation of the title compound, and yields a well crystallized product. Fig. 1 shows the asymmetric unit of the title compound. The cationic ruthenium complex exhibits the well known three-legged piano stool geometry with Cp as the seat and Ru—P1 = 2.3585 (4) Å, Ru—P2 = 2.3312 (4) Å, and Ru—N = 2.0422 (15) Å as the legs. The distance between Ru and the centroid of the π-bonded cyclopentadienyl moiety is 1.8579 (8) Å (ring slippage 0.052 Å) and the mean value of the Ru—C bond distances is 2.216 (19) Å. These dimensions agree well with those of the several related complexes, e.g. [CpRu(PPh₃)₂(NCCH₃)]BF₄ (Carreón et al., 1997) or [CpRu(PPh₃)₂(NCPh)]PF₆ (Cordiner et al., 2003). The conformation of the complex in the title compound is irregular and lacks a frequently encountered feature of CpRu(PPh₃)₂X complexes of having an intramolecular π-π-stacking contact between two phenyl rings opposite to the Cp ring, present for instance in [CpRu(PPh₃)₂(NCPh)]PF₆ (Carreon et al., 1997). A packing diagram of the crystal structure is shown in Fig. 2. Coherence between the complexes and the CF₃SO₃ anions is provided by C—H···π, C—H···O and C—H···F interactions, the most significant of which are listed in Table 1. Intermolecular π-π-stacking interactions are absent in the structure.

Related literature top

For the application of nitrile-substituted ruthenium–cyclopentadienyl complexes in catalysis, see: Trost et al. (2001). For the synthesis, chemistry and crystal structures of related ruthenium–cyclopentadienyl complexes, see: Carreón et al. (1997); Cordiner et al. (2003); Mauthner et al. (1999); Rüba et al. (1999, 2002); Bruce et al. (1982).

Experimental top

The synthesis of the title compound was carried out by stirring stoichiometric amounts of [CpRu(PPh₃)₂Cl] (Bruce et al., 1982) and AgCF₃SO₃ in technical nitromethane at room temperature for several hours. After removing AgCl by filtration through celite, the solution was stored over diethyl ether whereupon well facetted blocky yellow crystals precipitated, showing a distinctly hemimorphic habit with a roof like termination on one side of the b-axis (monoclinic, space group P2₁) and a flat base on the other.

Structure description top

For the application of nitrile-substituted ruthenium–cyclopentadienyl complexes in catalysis, see: Trost et al. (2001). For the synthesis, chemistry and crystal structures of related ruthenium–cyclopentadienyl complexes, see: Carreón et al. (1997); Cordiner et al. (2003); Mauthner et al. (1999); Rüba et al. (1999, 2002); Bruce et al. (1982).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT, SADABS and XPREP (Bruker, 2003); 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

	Fig. 1. Perspective view of the title compound with the atom numbering scheme. Displacement ellipsoids are at the 50% probability level. Arene bonded hydrogen atoms omitted for clarity.
	Fig. 2. Packing diagram of the title compound viewed down the a axis. H atoms omitted for clarity.

(η⁵-Cyclopentadienyl)(propionitrile-κN)bis(triphenylphosphine- κP)ruthenium(II) trifluoromethanesulfonate top

Crystal data top

[Ru(C₅H₅)(C₃H₅N)(C₁₈H₁₅P)₂]CF₃SO₃	F(000) = 916
M_r = 894.85	D_x = 1.507 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9696 reflections
a = 9.9991 (4) Å	θ = 2.3–30.0°
b = 17.2172 (7) Å	µ = 0.59 mm⁻¹
c = 11.4605 (5) Å	T = 123 K
β = 92.126 (1)°	Block, yellow
V = 1971.64 (14) Å³	0.31 × 0.21 × 0.20 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	11391 independent reflections
Radiation source: fine-focus sealed tube	11056 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and φ scans	θ_max = 30.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −14→14
T_min = 0.79, T_max = 0.89	k = −24→24
29537 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.061	w = 1/[σ²(F_o²) + (0.0394P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.008
11391 reflections	Δρ_max = 0.83 e Å⁻³
505 parameters	Δρ_min = −0.24 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 5488 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.038 (12)

Crystal data top

[Ru(C₅H₅)(C₃H₅N)(C₁₈H₁₅P)₂]CF₃SO₃	V = 1971.64 (14) Å³
M_r = 894.85	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.9991 (4) Å	µ = 0.59 mm⁻¹
b = 17.2172 (7) Å	T = 123 K
c = 11.4605 (5) Å	0.31 × 0.21 × 0.20 mm
β = 92.126 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	11391 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	11056 reflections with I > 2σ(I)
T_min = 0.79, T_max = 0.89	R_int = 0.023
29537 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.061	Δρ_max = 0.83 e Å⁻³
S = 1.02	Δρ_min = −0.24 e Å⁻³
11391 reflections	Absolute structure: Flack (1983), 5488 Friedel pairs
505 parameters	Absolute structure parameter: −0.038 (12)
1 restraint

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

	x	y	z	U_iso*/U_eq
Ru	0.341326 (11)	0.249998 (7)	0.726654 (9)	0.01426 (3)
C1	0.53032 (17)	0.19188 (12)	0.67577 (17)	0.0228 (4)
H1	0.5389	0.1642	0.6047	0.027*
C2	0.49161 (18)	0.15963 (12)	0.78263 (19)	0.0294 (4)
H2	0.4710	0.1066	0.7960	0.035*
C3	0.4887 (2)	0.22017 (16)	0.86681 (18)	0.0380 (6)
H3	0.4643	0.2151	0.9458	0.046*
C4	0.52913 (19)	0.28964 (14)	0.8112 (2)	0.0350 (5)
H4	0.5379	0.3392	0.8470	0.042*
C5	0.55426 (17)	0.27207 (11)	0.69210 (18)	0.0246 (4)
H5	0.5819	0.3077	0.6345	0.029*
N	0.25756 (14)	0.23010 (8)	0.56417 (13)	0.0188 (3)
C6	0.21203 (17)	0.21621 (11)	0.47390 (15)	0.0219 (3)
C7	0.1453 (2)	0.19964 (15)	0.35985 (17)	0.0342 (5)
H7A	0.2063	0.2138	0.2972	0.041*
H7B	0.0644	0.2325	0.3507	0.041*
C8	0.1054 (2)	0.11580 (17)	0.3454 (2)	0.0469 (6)
H8A	0.0617	0.1083	0.2683	0.070*
H8B	0.0432	0.1016	0.4060	0.070*
H8C	0.1852	0.0829	0.3526	0.070*
P1	0.15565 (4)	0.18985 (3)	0.80997 (4)	0.01583 (8)
C9	0.01753 (16)	0.15322 (10)	0.71392 (15)	0.0190 (3)
C10	−0.03505 (17)	0.20098 (11)	0.62471 (15)	0.0210 (3)
H10	0.0020	0.2511	0.6134	0.025*
C11	−0.14125 (18)	0.17569 (13)	0.55243 (18)	0.0265 (4)
H11	−0.1762	0.2086	0.4922	0.032*
C12	−0.1962 (2)	0.10270 (14)	0.56792 (19)	0.0283 (4)
H12	−0.2662	0.0847	0.5165	0.034*
C13	−0.14818 (19)	0.05593 (13)	0.65905 (19)	0.0292 (4)
H13	−0.1878	0.0067	0.6720	0.035*
C14	−0.04185 (19)	0.08125 (11)	0.73145 (18)	0.0241 (4)
H14	−0.0095	0.0490	0.7935	0.029*
C15	0.06383 (16)	0.24013 (10)	0.92283 (14)	0.0179 (3)
C16	0.13777 (18)	0.27803 (11)	1.01128 (15)	0.0219 (3)
H16	0.2327	0.2778	1.0102	0.026*
C17	0.0747 (2)	0.31616 (12)	1.10118 (17)	0.0285 (4)
H17	0.1263	0.3418	1.1609	0.034*
C18	−0.0637 (2)	0.31647 (13)	1.10291 (18)	0.0311 (4)
H18	−0.1073	0.3421	1.1643	0.037*
C19	−0.1390 (2)	0.27944 (13)	1.01531 (18)	0.0294 (4)
H19	−0.2339	0.2800	1.0168	0.035*
C20	−0.07604 (16)	0.24154 (12)	0.92526 (15)	0.0221 (3)
H20	−0.1281	0.2165	0.8653	0.027*
C21	0.21005 (17)	0.10030 (11)	0.88407 (16)	0.0202 (3)
C22	0.2503 (2)	0.03787 (12)	0.81551 (19)	0.0263 (4)
H22	0.2428	0.0416	0.7328	0.032*
C23	0.3009 (2)	−0.02938 (12)	0.8667 (2)	0.0321 (4)
H23	0.3278	−0.0714	0.8193	0.039*
C24	0.3122 (2)	−0.03525 (13)	0.9867 (2)	0.0388 (5)
H24	0.3475	−0.0813	1.0217	0.047*
C25	0.2728 (3)	0.02520 (14)	1.0559 (2)	0.0397 (5)
H25	0.2809	0.0207	1.1384	0.048*
C26	0.2204 (2)	0.09356 (12)	1.00511 (18)	0.0283 (4)
H26	0.1921	0.1350	1.0532	0.034*
P2	0.26534 (4)	0.37799 (2)	0.71997 (4)	0.01567 (8)
C27	0.25610 (17)	0.43943 (10)	0.84958 (16)	0.0183 (3)
C28	0.32721 (18)	0.42172 (11)	0.95327 (16)	0.0216 (3)
H28	0.3744	0.3739	0.9603	0.026*
C29	0.3294 (2)	0.47364 (13)	1.04651 (17)	0.0279 (4)
H29	0.3778	0.4610	1.1169	0.034*
C30	0.2619 (2)	0.54327 (13)	1.03735 (19)	0.0309 (4)
H30	0.2640	0.5786	1.1011	0.037*
C31	0.1907 (2)	0.56177 (12)	0.93457 (19)	0.0306 (4)
H31	0.1438	0.6096	0.9281	0.037*
C32	0.18831 (19)	0.51047 (11)	0.84190 (17)	0.0242 (4)
H32	0.1398	0.5236	0.7718	0.029*
C33	0.09830 (17)	0.39283 (10)	0.65273 (16)	0.0189 (3)
C34	0.07442 (19)	0.39834 (12)	0.53252 (17)	0.0259 (4)
H34	0.1479	0.3999	0.4823	0.031*
C35	−0.0560 (2)	0.40153 (13)	0.48482 (19)	0.0323 (4)
H35	−0.0710	0.4050	0.4026	0.039*
C36	−0.1634 (2)	0.39960 (14)	0.5577 (2)	0.0342 (5)
H36	−0.2522	0.4015	0.5254	0.041*
C37	−0.14138 (19)	0.39498 (12)	0.6774 (2)	0.0303 (4)
H37	−0.2153	0.3943	0.7272	0.036*
C38	−0.01191 (18)	0.39134 (11)	0.72506 (17)	0.0227 (4)
H38	0.0022	0.3878	0.8073	0.027*
C39	0.37796 (17)	0.43733 (10)	0.63223 (15)	0.0183 (3)
C40	0.44301 (18)	0.50304 (11)	0.67898 (17)	0.0216 (3)
H40	0.4272	0.5188	0.7567	0.026*
C41	0.53071 (19)	0.54539 (11)	0.61214 (19)	0.0255 (4)
H41	0.5756	0.5892	0.6452	0.031*
C42	0.55316 (18)	0.52433 (11)	0.49815 (18)	0.0248 (4)
H42	0.6118	0.5541	0.4526	0.030*
C43	0.48912 (18)	0.45894 (11)	0.45029 (17)	0.0226 (3)
H43	0.5034	0.4445	0.3717	0.027*
C44	0.40455 (17)	0.41509 (10)	0.51753 (16)	0.0197 (3)
H44	0.3642	0.3695	0.4856	0.024*
S	0.46664 (5)	0.27200 (3)	0.20757 (4)	0.02305 (9)
O1	0.53116 (16)	0.30544 (10)	0.10892 (13)	0.0332 (3)
O2	0.38633 (16)	0.32535 (10)	0.27204 (14)	0.0360 (3)
O3	0.40770 (16)	0.19647 (9)	0.18699 (14)	0.0347 (3)
C45	0.60750 (17)	0.25111 (16)	0.30810 (15)	0.0274 (3)
F1	0.56484 (15)	0.22620 (9)	0.41086 (11)	0.0455 (4)
F2	0.68724 (15)	0.19662 (10)	0.26773 (13)	0.0459 (4)
F3	0.68194 (14)	0.31414 (8)	0.33035 (12)	0.0395 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru	0.01224 (5)	0.01522 (5)	0.01522 (5)	0.00110 (5)	−0.00081 (3)	−0.00111 (5)
C1	0.0122 (7)	0.0272 (10)	0.0290 (9)	0.0040 (7)	0.0013 (6)	−0.0069 (8)
C2	0.0172 (8)	0.0293 (10)	0.0418 (11)	0.0081 (7)	0.0006 (7)	0.0111 (8)
C3	0.0190 (8)	0.0745 (17)	0.0199 (9)	0.0123 (9)	−0.0045 (7)	0.0028 (9)
C4	0.0137 (8)	0.0408 (12)	0.0495 (13)	0.0055 (8)	−0.0103 (8)	−0.0256 (10)
C5	0.0125 (7)	0.0238 (9)	0.0374 (10)	−0.0012 (6)	0.0008 (6)	0.0034 (7)
N	0.0171 (6)	0.0182 (7)	0.0211 (7)	−0.0005 (5)	0.0006 (5)	0.0000 (5)
C6	0.0204 (8)	0.0243 (9)	0.0209 (8)	−0.0042 (7)	−0.0002 (6)	−0.0002 (7)
C7	0.0299 (10)	0.0531 (14)	0.0191 (9)	−0.0133 (9)	−0.0054 (7)	0.0005 (9)
C8	0.0344 (12)	0.0593 (17)	0.0468 (14)	−0.0084 (11)	−0.0002 (10)	−0.0244 (13)
P1	0.01420 (18)	0.01554 (19)	0.01770 (19)	0.00049 (15)	0.00011 (13)	−0.00047 (15)
C9	0.0147 (7)	0.0207 (8)	0.0215 (8)	−0.0007 (6)	0.0004 (6)	−0.0041 (6)
C10	0.0151 (7)	0.0230 (8)	0.0247 (8)	0.0001 (6)	−0.0020 (6)	−0.0025 (7)
C11	0.0157 (8)	0.0347 (10)	0.0289 (9)	0.0020 (7)	−0.0035 (6)	−0.0034 (8)
C12	0.0168 (8)	0.0367 (11)	0.0313 (10)	−0.0010 (8)	−0.0022 (7)	−0.0129 (9)
C13	0.0221 (9)	0.0278 (10)	0.0377 (11)	−0.0060 (7)	0.0036 (8)	−0.0104 (8)
C14	0.0222 (9)	0.0220 (9)	0.0281 (9)	−0.0023 (7)	0.0026 (7)	−0.0019 (7)
C15	0.0177 (7)	0.0156 (9)	0.0206 (7)	0.0029 (6)	0.0033 (5)	0.0012 (6)
C16	0.0212 (8)	0.0219 (8)	0.0226 (8)	0.0021 (6)	0.0013 (6)	−0.0006 (7)
C17	0.0338 (10)	0.0281 (10)	0.0235 (9)	0.0030 (8)	0.0026 (8)	−0.0056 (7)
C18	0.0341 (10)	0.0311 (10)	0.0287 (9)	0.0095 (8)	0.0103 (8)	−0.0040 (8)
C19	0.0219 (9)	0.0316 (9)	0.0351 (10)	0.0058 (7)	0.0086 (7)	0.0026 (8)
C20	0.0192 (7)	0.0221 (9)	0.0253 (7)	0.0022 (7)	0.0035 (5)	0.0008 (7)
C21	0.0175 (7)	0.0165 (8)	0.0265 (8)	0.0000 (6)	−0.0005 (6)	0.0016 (6)
C22	0.0248 (9)	0.0207 (9)	0.0336 (10)	0.0026 (7)	0.0065 (8)	−0.0013 (8)
C23	0.0273 (9)	0.0189 (9)	0.0502 (12)	0.0043 (7)	0.0016 (9)	−0.0026 (9)
C24	0.0394 (12)	0.0218 (10)	0.0541 (14)	0.0055 (9)	−0.0135 (10)	0.0076 (10)
C25	0.0531 (15)	0.0310 (11)	0.0340 (12)	0.0062 (11)	−0.0118 (11)	0.0068 (9)
C26	0.0351 (10)	0.0214 (9)	0.0280 (10)	0.0017 (8)	−0.0051 (8)	−0.0001 (7)
P2	0.01508 (18)	0.01485 (18)	0.01694 (18)	0.00050 (15)	−0.00126 (14)	−0.00113 (15)
C27	0.0177 (7)	0.0174 (8)	0.0199 (8)	−0.0006 (6)	0.0009 (6)	−0.0024 (6)
C28	0.0212 (8)	0.0219 (8)	0.0217 (8)	−0.0005 (6)	0.0011 (6)	−0.0021 (6)
C29	0.0293 (10)	0.0345 (11)	0.0198 (8)	−0.0008 (8)	−0.0007 (7)	−0.0052 (8)
C30	0.0295 (10)	0.0344 (11)	0.0289 (10)	−0.0022 (8)	0.0034 (8)	−0.0146 (8)
C31	0.0304 (10)	0.0237 (9)	0.0377 (11)	0.0052 (8)	0.0025 (8)	−0.0106 (8)
C32	0.0242 (9)	0.0213 (9)	0.0271 (9)	0.0032 (7)	−0.0017 (7)	−0.0028 (7)
C33	0.0165 (7)	0.0151 (8)	0.0248 (8)	0.0006 (6)	−0.0035 (6)	−0.0003 (6)
C34	0.0232 (8)	0.0270 (9)	0.0269 (9)	−0.0022 (7)	−0.0059 (7)	0.0048 (7)
C35	0.0282 (9)	0.0326 (11)	0.0351 (11)	0.0002 (8)	−0.0133 (8)	0.0047 (9)
C36	0.0182 (9)	0.0282 (11)	0.0550 (14)	0.0020 (8)	−0.0121 (9)	−0.0015 (10)
C37	0.0184 (8)	0.0254 (10)	0.0468 (12)	0.0011 (7)	−0.0004 (8)	−0.0048 (9)
C38	0.0202 (8)	0.0187 (9)	0.0290 (9)	−0.0001 (7)	−0.0011 (7)	−0.0017 (7)
C39	0.0166 (7)	0.0162 (7)	0.0221 (8)	0.0010 (6)	−0.0004 (6)	0.0013 (6)
C40	0.0205 (8)	0.0186 (8)	0.0258 (8)	−0.0013 (6)	0.0001 (6)	−0.0030 (6)
C41	0.0202 (8)	0.0193 (9)	0.0368 (10)	−0.0037 (7)	0.0012 (7)	−0.0012 (7)
C42	0.0207 (8)	0.0206 (9)	0.0331 (10)	0.0018 (7)	0.0028 (7)	0.0066 (7)
C43	0.0221 (8)	0.0219 (9)	0.0242 (9)	0.0033 (7)	0.0048 (7)	0.0014 (7)
C44	0.0190 (8)	0.0168 (8)	0.0233 (8)	−0.0001 (6)	−0.0005 (6)	−0.0011 (6)
S	0.0246 (2)	0.0236 (2)	0.02063 (19)	−0.00254 (16)	−0.00403 (16)	−0.00122 (15)
O1	0.0360 (8)	0.0380 (8)	0.0252 (7)	−0.0037 (7)	−0.0027 (6)	0.0067 (6)
O2	0.0315 (7)	0.0410 (9)	0.0352 (8)	0.0058 (7)	−0.0030 (6)	−0.0090 (7)
O3	0.0391 (8)	0.0279 (7)	0.0365 (8)	−0.0110 (7)	−0.0083 (6)	−0.0012 (6)
C45	0.0287 (8)	0.0288 (8)	0.0243 (7)	−0.0020 (10)	−0.0050 (6)	0.0039 (10)
F1	0.0506 (8)	0.0623 (10)	0.0230 (6)	−0.0067 (7)	−0.0065 (5)	0.0146 (6)
F2	0.0417 (7)	0.0473 (9)	0.0477 (9)	0.0181 (7)	−0.0103 (6)	−0.0071 (7)
F3	0.0374 (7)	0.0382 (7)	0.0417 (7)	−0.0098 (6)	−0.0163 (6)	−0.0013 (6)

Geometric parameters (Å, º) top

Ru—N	2.0422 (15)	C22—C23	1.385 (3)
Ru—C4	2.1901 (19)	C22—H22	0.9500
Ru—C3	2.2001 (19)	C23—C24	1.379 (4)
Ru—C5	2.2129 (17)	C23—H23	0.9500
Ru—C1	2.2348 (17)	C24—C25	1.375 (4)
Ru—C2	2.2403 (18)	C24—H24	0.9500
Ru—P2	2.3312 (4)	C25—C26	1.406 (3)
Ru—P1	2.3585 (4)	C25—H25	0.9500
C1—C2	1.412 (3)	C26—H26	0.9500
C1—C5	1.412 (3)	P2—C27	1.8288 (18)
C1—H1	0.9500	P2—C33	1.8312 (17)
C2—C3	1.421 (3)	P2—C39	1.8458 (18)
C2—H2	0.9500	C27—C28	1.396 (3)
C3—C4	1.421 (4)	C27—C32	1.399 (3)
C3—H3	0.9500	C28—C29	1.393 (3)
C4—C5	1.430 (3)	C28—H28	0.9500
C4—H4	0.9500	C29—C30	1.378 (3)
C5—H5	0.9500	C29—H29	0.9500
N—C6	1.140 (2)	C30—C31	1.390 (3)
C6—C7	1.473 (3)	C30—H30	0.9500
C7—C8	1.505 (4)	C31—C32	1.381 (3)
C7—H7A	0.9900	C31—H31	0.9500
C7—H7B	0.9900	C32—H32	0.9500
C8—H8A	0.9800	C33—C34	1.393 (3)
C8—H8B	0.9800	C33—C38	1.404 (3)
C8—H8C	0.9800	C34—C35	1.396 (3)
P1—C15	1.8312 (17)	C34—H34	0.9500
P1—C21	1.8331 (18)	C35—C36	1.385 (3)
P1—C9	1.8451 (17)	C35—H35	0.9500
C9—C14	1.392 (3)	C36—C37	1.384 (3)
C9—C10	1.399 (2)	C36—H36	0.9500
C10—C11	1.392 (2)	C37—C38	1.388 (3)
C10—H10	0.9500	C37—H37	0.9500
C11—C12	1.386 (3)	C38—H38	0.9500
C11—H11	0.9500	C39—C40	1.401 (2)
C12—C13	1.390 (3)	C39—C44	1.404 (2)
C12—H12	0.9500	C40—C41	1.392 (3)
C13—C14	1.394 (3)	C40—H40	0.9500
C13—H13	0.9500	C41—C42	1.382 (3)
C14—H14	0.9500	C41—H41	0.9500
C15—C16	1.394 (2)	C42—C43	1.397 (3)
C15—C20	1.400 (2)	C42—H42	0.9500
C16—C17	1.392 (3)	C43—C44	1.388 (3)
C16—H16	0.9500	C43—H43	0.9500
C17—C18	1.385 (3)	C44—H44	0.9500
C17—H17	0.9500	S—O2	1.4418 (16)
C18—C19	1.387 (3)	S—O1	1.4422 (15)
C18—H18	0.9500	S—O3	1.4435 (16)
C19—C20	1.391 (3)	S—C45	1.8221 (17)
C19—H19	0.9500	C45—F2	1.326 (3)
C20—H20	0.9500	C45—F3	1.335 (3)
C21—C26	1.392 (3)	C45—F1	1.338 (2)
C21—C22	1.399 (3)

N—Ru—C4	140.51 (8)	C18—C17—C16	119.51 (19)
N—Ru—C3	150.17 (8)	C18—C17—H17	120.2
C4—Ru—C3	37.77 (10)	C16—C17—H17	120.2
N—Ru—C5	103.32 (7)	C17—C18—C19	120.24 (18)
C4—Ru—C5	37.89 (8)	C17—C18—H18	119.9
C3—Ru—C5	63.12 (8)	C19—C18—H18	119.9
N—Ru—C1	90.52 (6)	C18—C19—C20	120.26 (18)
C4—Ru—C1	62.32 (7)	C18—C19—H19	119.9
C3—Ru—C1	62.35 (8)	C20—C19—H19	119.9
C5—Ru—C1	37.03 (8)	C19—C20—C15	120.18 (17)
N—Ru—C2	113.12 (7)	C19—C20—H20	119.9
C4—Ru—C2	62.27 (9)	C15—C20—H20	119.9
C3—Ru—C2	37.32 (9)	C26—C21—C22	118.91 (18)
C5—Ru—C2	62.03 (7)	C26—C21—P1	122.79 (15)
C1—Ru—C2	36.78 (7)	C22—C21—P1	118.20 (15)
N—Ru—P2	90.37 (4)	C23—C22—C21	120.8 (2)
C4—Ru—P2	89.60 (6)	C23—C22—H22	119.6
C3—Ru—P2	116.96 (7)	C21—C22—H22	119.6
C5—Ru—P2	98.42 (5)	C24—C23—C22	119.9 (2)
C1—Ru—P2	133.82 (5)	C24—C23—H23	120.0
C2—Ru—P2	151.67 (6)	C22—C23—H23	120.0
N—Ru—P1	89.61 (4)	C25—C24—C23	120.3 (2)
C4—Ru—P1	129.24 (7)	C25—C24—H24	119.9
C3—Ru—P1	96.78 (6)	C23—C24—H24	119.9
C5—Ru—P1	157.66 (5)	C24—C25—C26	120.4 (2)
C1—Ru—P1	126.52 (6)	C24—C25—H25	119.8
C2—Ru—P1	96.25 (5)	C26—C25—H25	119.8
P2—Ru—P1	99.661 (15)	C21—C26—C25	119.7 (2)
C2—C1—C5	108.67 (17)	C21—C26—H26	120.2
C2—C1—Ru	71.82 (10)	C25—C26—H26	120.2
C5—C1—Ru	70.64 (10)	C27—P2—C33	100.86 (8)
C2—C1—H1	125.7	C27—P2—C39	99.93 (8)
C5—C1—H1	125.7	C33—P2—C39	105.01 (8)
Ru—C1—H1	123.5	C27—P2—Ru	123.12 (6)
C1—C2—C3	108.27 (19)	C33—P2—Ru	115.90 (6)
C1—C2—Ru	71.40 (10)	C39—P2—Ru	109.66 (6)
C3—C2—Ru	69.80 (11)	C28—C27—C32	118.34 (17)
C1—C2—H2	125.9	C28—C27—P2	121.71 (14)
C3—C2—H2	125.9	C32—C27—P2	119.57 (14)
Ru—C2—H2	124.5	C29—C28—C27	120.41 (18)
C4—C3—C2	107.44 (18)	C29—C28—H28	119.8
C4—C3—Ru	70.73 (11)	C27—C28—H28	119.8
C2—C3—Ru	72.87 (11)	C30—C29—C28	120.40 (19)
C4—C3—H3	126.3	C30—C29—H29	119.8
C2—C3—H3	126.3	C28—C29—H29	119.8
Ru—C3—H3	121.8	C29—C30—C31	119.85 (18)
C3—C4—C5	108.24 (19)	C29—C30—H30	120.1
C3—C4—Ru	71.50 (11)	C31—C30—H30	120.1
C5—C4—Ru	71.92 (10)	C32—C31—C30	119.93 (19)
C3—C4—H4	125.9	C32—C31—H31	120.0
C5—C4—H4	125.9	C30—C31—H31	120.0
Ru—C4—H4	122.4	C31—C32—C27	121.06 (18)
C1—C5—C4	107.36 (18)	C31—C32—H32	119.5
C1—C5—Ru	72.33 (10)	C27—C32—H32	119.5
C4—C5—Ru	70.19 (10)	C34—C33—C38	118.42 (16)
C1—C5—H5	126.3	C34—C33—P2	123.09 (14)
C4—C5—H5	126.3	C38—C33—P2	118.21 (13)
Ru—C5—H5	122.8	C33—C34—C35	120.89 (19)
C6—N—Ru	177.51 (15)	C33—C34—H34	119.6
N—C6—C7	176.6 (2)	C35—C34—H34	119.6
C6—C7—C8	113.1 (2)	C36—C35—C34	119.8 (2)
C6—C7—H7A	109.0	C36—C35—H35	120.1
C8—C7—H7A	109.0	C34—C35—H35	120.1
C6—C7—H7B	109.0	C37—C36—C35	120.06 (19)
C8—C7—H7B	109.0	C37—C36—H36	120.0
H7A—C7—H7B	107.8	C35—C36—H36	120.0
C7—C8—H8A	109.5	C36—C37—C38	120.3 (2)
C7—C8—H8B	109.5	C36—C37—H37	119.8
H8A—C8—H8B	109.5	C38—C37—H37	119.8
C7—C8—H8C	109.5	C37—C38—C33	120.53 (19)
H8A—C8—H8C	109.5	C37—C38—H38	119.7
H8B—C8—H8C	109.5	C33—C38—H38	119.7
C15—P1—C21	102.61 (8)	C40—C39—C44	118.47 (16)
C15—P1—C9	101.49 (8)	C40—C39—P2	121.50 (14)
C21—P1—C9	101.04 (8)	C44—C39—P2	119.98 (13)
C15—P1—Ru	120.08 (6)	C41—C40—C39	120.36 (17)
C21—P1—Ru	109.41 (6)	C41—C40—H40	119.8
C9—P1—Ru	119.45 (6)	C39—C40—H40	119.8
C14—C9—C10	118.55 (16)	C42—C41—C40	120.70 (18)
C14—C9—P1	122.15 (14)	C42—C41—H41	119.7
C10—C9—P1	119.19 (13)	C40—C41—H41	119.7
C11—C10—C9	120.57 (18)	C41—C42—C43	119.62 (18)
C11—C10—H10	119.7	C41—C42—H42	120.2
C9—C10—H10	119.7	C43—C42—H42	120.2
C12—C11—C10	120.31 (19)	C44—C43—C42	120.00 (18)
C12—C11—H11	119.8	C44—C43—H43	120.0
C10—C11—H11	119.8	C42—C43—H43	120.0
C11—C12—C13	119.61 (18)	C43—C44—C39	120.79 (17)
C11—C12—H12	120.2	C43—C44—H44	119.6
C13—C12—H12	120.2	C39—C44—H44	119.6
C12—C13—C14	120.0 (2)	O2—S—O1	114.91 (10)
C12—C13—H13	120.0	O2—S—O3	115.21 (10)
C14—C13—H13	120.0	O1—S—O3	115.05 (10)
C9—C14—C13	120.83 (19)	O2—S—C45	103.52 (10)
C9—C14—H14	119.6	O1—S—C45	102.52 (9)
C13—C14—H14	119.6	O3—S—C45	103.11 (11)
C16—C15—C20	118.72 (16)	F2—C45—F3	107.67 (16)
C16—C15—P1	117.93 (12)	F2—C45—F1	107.2 (2)
C20—C15—P1	123.34 (13)	F3—C45—F1	106.62 (16)
C17—C16—C15	121.08 (17)	F2—C45—S	112.32 (13)
C17—C16—H16	119.5	F3—C45—S	111.88 (16)
C15—C16—H16	119.5	F1—C45—S	110.84 (12)

N—Ru—C1—C2	−130.06 (13)	C10—C11—C12—C13	2.5 (3)
C4—Ru—C1—C2	79.87 (15)	C11—C12—C13—C14	−2.5 (3)
C3—Ru—C1—C2	37.00 (14)	C10—C9—C14—C13	2.4 (3)
C5—Ru—C1—C2	118.20 (17)	P1—C9—C14—C13	178.46 (14)
P2—Ru—C1—C2	138.93 (11)	C12—C13—C14—C9	0.0 (3)
P1—Ru—C1—C2	−40.16 (14)	C21—P1—C15—C16	77.57 (15)
N—Ru—C1—C5	111.75 (12)	C9—P1—C15—C16	−178.21 (14)
C4—Ru—C1—C5	−38.32 (13)	Ru—P1—C15—C16	−43.98 (16)
C3—Ru—C1—C5	−81.19 (14)	C21—P1—C15—C20	−101.66 (16)
C2—Ru—C1—C5	−118.20 (17)	C9—P1—C15—C20	2.57 (17)
P2—Ru—C1—C5	20.73 (14)	Ru—P1—C15—C20	136.79 (14)
P1—Ru—C1—C5	−158.36 (10)	C20—C15—C16—C17	0.5 (3)
C5—C1—C2—C3	1.0 (2)	P1—C15—C16—C17	−178.74 (15)
Ru—C1—C2—C3	−60.35 (13)	C15—C16—C17—C18	0.0 (3)
C5—C1—C2—Ru	61.37 (13)	C16—C17—C18—C19	−0.4 (3)
N—Ru—C2—C1	56.32 (13)	C17—C18—C19—C20	0.2 (3)
C4—Ru—C2—C1	−80.02 (14)	C18—C19—C20—C15	0.4 (3)
C3—Ru—C2—C1	−118.44 (18)	C16—C15—C20—C19	−0.7 (3)
C5—Ru—C2—C1	−36.94 (12)	P1—C15—C20—C19	178.51 (14)
P2—Ru—C2—C1	−87.45 (16)	C15—P1—C21—C26	−21.73 (18)
P1—Ru—C2—C1	148.57 (11)	C9—P1—C21—C26	−126.30 (17)
N—Ru—C2—C3	174.76 (12)	Ru—P1—C21—C26	106.84 (16)
C4—Ru—C2—C3	38.41 (13)	C15—P1—C21—C22	162.15 (15)
C5—Ru—C2—C3	81.50 (14)	C9—P1—C21—C22	57.57 (16)
C1—Ru—C2—C3	118.44 (18)	Ru—P1—C21—C22	−69.29 (15)
P2—Ru—C2—C3	30.99 (19)	C26—C21—C22—C23	−0.7 (3)
P1—Ru—C2—C3	−92.99 (13)	P1—C21—C22—C23	175.61 (15)
C1—C2—C3—C4	−1.3 (2)	C21—C22—C23—C24	−0.1 (3)
Ru—C2—C3—C4	−62.70 (13)	C22—C23—C24—C25	0.4 (4)
C1—C2—C3—Ru	61.36 (13)	C23—C24—C25—C26	0.0 (4)
N—Ru—C3—C4	106.38 (19)	C22—C21—C26—C25	1.1 (3)
C5—Ru—C3—C4	37.78 (11)	P1—C21—C26—C25	−175.01 (17)
C1—Ru—C3—C4	79.63 (12)	C24—C25—C26—C21	−0.8 (4)
C2—Ru—C3—C4	116.10 (17)	N—Ru—P2—C27	163.43 (8)
P2—Ru—C3—C4	−47.99 (12)	C4—Ru—P2—C27	−56.06 (10)
P1—Ru—C3—C4	−152.47 (11)	C3—Ru—P2—C27	−28.99 (10)
N—Ru—C3—C2	−9.7 (2)	C5—Ru—P2—C27	−93.04 (9)
C4—Ru—C3—C2	−116.10 (17)	C1—Ru—P2—C27	−105.49 (10)
C5—Ru—C3—C2	−78.32 (13)	C2—Ru—P2—C27	−49.49 (14)
C1—Ru—C3—C2	−36.47 (12)	P1—Ru—P2—C27	73.77 (7)
P2—Ru—C3—C2	−164.09 (10)	N—Ru—P2—C33	38.91 (8)
P1—Ru—C3—C2	91.43 (12)	C4—Ru—P2—C33	179.42 (9)
C2—C3—C4—C5	1.2 (2)	C3—Ru—P2—C33	−153.51 (9)
Ru—C3—C4—C5	−62.94 (13)	C5—Ru—P2—C33	142.44 (8)
C2—C3—C4—Ru	64.10 (13)	C1—Ru—P2—C33	129.99 (9)
N—Ru—C4—C3	−131.38 (14)	C2—Ru—P2—C33	−174.01 (13)
C5—Ru—C4—C3	−117.16 (18)	P1—Ru—P2—C33	−50.75 (7)
C1—Ru—C4—C3	−79.71 (13)	N—Ru—P2—C39	−79.71 (7)
C2—Ru—C4—C3	−37.96 (12)	C4—Ru—P2—C39	60.79 (9)
P2—Ru—C4—C3	138.52 (12)	C3—Ru—P2—C39	87.86 (9)
P1—Ru—C4—C3	36.34 (14)	C5—Ru—P2—C39	23.81 (8)
N—Ru—C4—C5	−14.22 (19)	C1—Ru—P2—C39	11.36 (9)
C3—Ru—C4—C5	117.16 (18)	C2—Ru—P2—C39	67.36 (13)
C1—Ru—C4—C5	37.45 (12)	P1—Ru—P2—C39	−169.38 (6)
C2—Ru—C4—C5	79.20 (13)	C33—P2—C27—C28	149.20 (15)
P2—Ru—C4—C5	−104.32 (12)	C39—P2—C27—C28	−103.26 (16)
P1—Ru—C4—C5	153.50 (10)	Ru—P2—C27—C28	18.20 (18)
C2—C1—C5—C4	−0.3 (2)	C33—P2—C27—C32	−37.97 (17)
Ru—C1—C5—C4	61.82 (12)	C39—P2—C27—C32	69.56 (16)
C2—C1—C5—Ru	−62.11 (12)	Ru—P2—C27—C32	−168.97 (12)
C3—C4—C5—C1	−0.5 (2)	C32—C27—C28—C29	0.3 (3)
Ru—C4—C5—C1	−63.21 (13)	P2—C27—C28—C29	173.25 (15)
C3—C4—C5—Ru	62.67 (13)	C27—C28—C29—C30	−0.3 (3)
N—Ru—C5—C1	−72.64 (12)	C28—C29—C30—C31	0.2 (3)
C4—Ru—C5—C1	116.60 (18)	C29—C30—C31—C32	−0.2 (3)
C3—Ru—C5—C1	78.94 (13)	C30—C31—C32—C27	0.3 (3)
C2—Ru—C5—C1	36.69 (12)	C28—C27—C32—C31	−0.4 (3)
P2—Ru—C5—C1	−165.04 (10)	P2—C27—C32—C31	−173.44 (16)
P1—Ru—C5—C1	51.2 (2)	C27—P2—C33—C34	142.10 (16)
N—Ru—C5—C4	170.76 (13)	C39—P2—C33—C34	38.62 (17)
C3—Ru—C5—C4	−37.66 (14)	Ru—P2—C33—C34	−82.54 (16)
C1—Ru—C5—C4	−116.60 (18)	C27—P2—C33—C38	−43.99 (16)
C2—Ru—C5—C4	−79.90 (14)	C39—P2—C33—C38	−147.47 (14)
P2—Ru—C5—C4	78.37 (13)	Ru—P2—C33—C38	91.37 (14)
P1—Ru—C5—C4	−65.4 (2)	C38—C33—C34—C35	−0.6 (3)
N—Ru—P1—C15	−127.55 (7)	P2—C33—C34—C35	173.26 (16)
C4—Ru—P1—C15	60.22 (10)	C33—C34—C35—C36	0.3 (3)
C3—Ru—P1—C15	81.66 (9)	C34—C35—C36—C37	0.4 (3)
C5—Ru—P1—C15	106.34 (15)	C35—C36—C37—C38	−0.7 (3)
C1—Ru—P1—C15	142.09 (9)	C36—C37—C38—C33	0.4 (3)
C2—Ru—P1—C15	119.23 (9)	C34—C33—C38—C37	0.3 (3)
P2—Ru—P1—C15	−37.24 (6)	P2—C33—C38—C37	−173.94 (15)
N—Ru—P1—C21	114.31 (8)	C27—P2—C39—C40	8.39 (16)
C4—Ru—P1—C21	−57.92 (10)	C33—P2—C39—C40	112.57 (15)
C3—Ru—P1—C21	−36.48 (9)	Ru—P2—C39—C40	−122.27 (13)
C5—Ru—P1—C21	−11.80 (16)	C27—P2—C39—C44	−174.34 (14)
C1—Ru—P1—C21	23.95 (9)	C33—P2—C39—C44	−70.16 (15)
C2—Ru—P1—C21	1.09 (9)	Ru—P2—C39—C44	55.00 (15)
P2—Ru—P1—C21	−155.39 (6)	C44—C39—C40—C41	0.7 (3)
N—Ru—P1—C9	−1.30 (8)	P2—C39—C40—C41	177.97 (14)
C4—Ru—P1—C9	−173.53 (10)	C39—C40—C41—C42	1.2 (3)
C3—Ru—P1—C9	−152.09 (9)	C40—C41—C42—C43	−1.3 (3)
C5—Ru—P1—C9	−127.40 (15)	C41—C42—C43—C44	−0.6 (3)
C1—Ru—P1—C9	−91.66 (9)	C42—C43—C44—C39	2.6 (3)
C2—Ru—P1—C9	−114.52 (9)	C40—C39—C44—C43	−2.6 (3)
P2—Ru—P1—C9	89.01 (7)	P2—C39—C44—C43	−179.92 (14)
C15—P1—C9—C14	−88.98 (16)	O2—S—C45—F2	174.08 (17)
C21—P1—C9—C14	16.49 (17)	O1—S—C45—F2	−66.11 (19)
Ru—P1—C9—C14	136.43 (13)	O3—S—C45—F2	53.69 (18)
C15—P1—C9—C10	87.08 (15)	O2—S—C45—F3	−64.69 (15)
C21—P1—C9—C10	−167.45 (14)	O1—S—C45—F3	55.12 (16)
Ru—P1—C9—C10	−47.51 (16)	O3—S—C45—F3	174.93 (14)
C14—C9—C10—C11	−2.4 (3)	O2—S—C45—F1	54.2 (2)
P1—C9—C10—C11	−178.57 (14)	O1—S—C45—F1	173.99 (17)
C9—C10—C11—C12	−0.1 (3)	O3—S—C45—F1	−66.21 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···F1	0.95	2.49	3.125 (2)	125
C3—H3···O1ⁱ	0.95	2.50	3.154 (3)	126
C7—H7A···O3	0.99	2.43	3.346 (3)	153
C28—H28···O1ⁱ	0.95	2.56	3.328 (2)	138
C44—H44···O2	0.95	2.58	3.209 (2)	124

Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formula	[Ru(C₅H₅)(C₃H₅N)(C₁₈H₁₅P)₂]CF₃SO₃
M_r	894.85
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	123
a, b, c (Å)	9.9991 (4), 17.2172 (7), 11.4605 (5)
β (°)	92.126 (1)
V (Å³)	1971.64 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.31 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.79, 0.89
No. of measured, independent and observed [I > 2σ(I)] reflections	29537, 11391, 11056
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.061, 1.02
No. of reflections	11391
No. of parameters	505
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.24
Absolute structure	Flack (1983), 5488 Friedel pairs
Absolute structure parameter	−0.038 (12)

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SADABS and XPREP (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···F1	0.95	2.49	3.125 (2)	124.5
C3—H3···O1ⁱ	0.95	2.50	3.154 (3)	125.7
C7—H7A···O3	0.99	2.43	3.346 (3)	152.9
C28—H28···O1ⁱ	0.95	2.56	3.328 (2)	138.2
C44—H44···O2	0.95	2.58	3.209 (2)	124.0

Symmetry code: (i) x, y, z+1.

References

Bruce, M. I., Hameister, C., Swincer, A. G., Wallis, R. C. & Ittel, S. D. (1982). Inorganic Synthesis, Vol. XXI, pp. 78–84. New York: John Wiley. Google Scholar
Bruker (2003). SMART, SAINT, SADABS and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carreón, O. Y., Leyva, M. A., Fernández-G., J. M. & Pénicaud, A. (1997). Acta Cryst. C53, 301–302. Google Scholar
Cordiner, R. L., Corcoran, D., Yufit, D. S., Goeta, A. E., Howard, J. A. K. & Low, P. J. (2003). Dalton Trans. pp. 3541–3549. Web of Science CSD CrossRef Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Mauthner, K., Soldouzi, K. M., Mereiter, K., Schmid, R. & Kirchner, K. (1999). Organometallics, 18, 4681–4683. Web of Science CSD CrossRef CAS Google Scholar
Rüba, E., Mereiter, K., Schmid, R., Sapunov, V. N., Kirchner, K., Schottenberger, H., Calhorda, M. C. & Veiros, L. F. (2002). Chem. Eur. J. 8, 3948–3961. PubMed Google Scholar
Rüba, E., Simanko, W., Mauthner, K., Soldouzi, K. M., Slugovc, C., Mereiter, K., Schmid, R. & Kirchner, K. (1999). Organometallics, 18, 3843–3850. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Trost, B. M., Toste, F. D. & Pinkerton, A. B. (2001). Chem. Rev. 101, 2067–2096. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 65| Part 11| November 2009| Page m1267

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