Chlorido(η6-N2-diphenylphosphanyl-N1,N1-diisopropyl-4-methoxybenz­amidine-κP)(triphenylphosphane-κP)ruthenium(II) trifluoromethansulfonate acetone disolvate

Kéchaou-Perrot, M.; Vendier, L.; Igau, A.

doi:10.1107/S1600536813029450

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages m659-m660

doi:10.1107/S1600536813029450

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Chlorido(η⁶-N²-diphenylphosphanyl-N¹,N¹-diisopropyl-4-methoxybenzamidine-κP)(triphenylphosphane-κP)ruthenium(II) trifluoromethansulfonate acetone disolvate

Manel Kéchaou-Perrot,^a Laure Vendier ^a ^* and Alain Igau ^a

^aLaboratoire de Chimie de Coordination, UPR-CNRS 8241, 205, route de Narbonne, 31077 Toulouse cedex, France
^*Correspondence e-mail: laure.vendier@lcc-toulouse.fr

(Received 16 September 2013; accepted 25 October 2013; online 13 November 2013)

In the title compound, [RuCl(C₁₈H₁₅P)(C₂₆H₃₁N₂OP)](CF₃O₃S)·2C₃H₆O, the Ru^II ion is coordinated in a three-legged piano stool, half-sandwich-type geometry by a chlorido ligand, a triphenylphosphine and a tethered η⁶-(phenyl-p-O-methoxy) κ¹-P N-diphenylphosphino N′-diisopropyl amidine ligand charge-balanced by a trifluormethansulfonate counter-anion. The η⁶-coordination mode of the arene incorporated into the structure was generated in situ after addition of methyl trifluoromethanesulfonate to the neutral η⁵-arene tethered precursor complex [RuCl(PPh₃)(η⁵:κ¹-OC₆H₄C(NiPr₂)=N-PPh₂)] in dichloromethane solution.

CCDC reference: 968713

Related literature

For related tethered η⁶-arene ruthenium(II) half-sandwich piano-stool complexes, see: Therrien & Ward (1999 ); Faller & D'Alliessi (2003 ); Cetinkaya et al. (2003 ); Cadierno et al. (2004 ); Ito et al. (2008 ); Arquier et al. (2009 ); Parekh et al. (2012 ). For η⁵-arene ruthenium(II) half-sandwich piano-stool complexes, see: Cole-Hamilton et al. (1976 ); Rosete et al. (1979 ); Snelgrove et al. (2005 ); Ferrando-Miguel et al. (2005 ). For the increasing medicinal interest in η⁶-arene ruthenium(II) half-sandwich complexes, see: Hartinger & Dyson (2009 ); Allardyce et al. (2001 ); Scolaro et al. (2005 ); Dyson (2007 ); Chatterjee et al. (2008 ). For the synthesis of the precursor, see: Kechaou et al. (2013 ).

Experimental

Crystal data

[RuCl(C₁₈H₁₅P)(C₂₆H₃₁N₂OP)](CF₃O₃S)·2C₃H₆O
M_r = 1082.51
Monoclinic, P 2₁ /c
a = 11.6970 (2) Å
b = 15.0260 (3) Å
c = 29.7770 (6) Å
β = 99.864 (2)°
V = 5156.21 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 180 K
0.19 × 0.1 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.933, T_max = 0.982
43527 measured reflections
10532 independent reflections
8192 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.089
S = 1.09
10532 reflections
608 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

Supporting information

CCDC reference: 968713

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813029450/cq2007sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029450/cq2007Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813029450/cq2007Isup3.cdx

checkCIF report

Comment top

In our efforts to prepare piano stool, half-sandwich, tethered functionalized η⁶-arene ruthenium(II) complexes, we investigated the reaction of the ruthenium(II) precursor complex RuCl(PPh3)(η⁵:κ¹-OC₆H₄C(NiPr₂)=N-PPh₂)] with methyl trifluoromethanesulfonate. The aim was to prepare quantitatively, as assessed by NMR spectroscopy, the corresponding functionalized η⁶-arene methoxy ruthenium(II) complex. It is noteworthy that alkylation on the carbonyl function of a coordinated η⁵-oxocyclohexadienyl ligand had never been reported before our studies. The title complex was isolated as a dark-yellow powder and crystals of suitable quality for XRD analysis were obtained by slow diffusion of pentane into an acetone solution of the complex. Single crystal X-ray analysis determined the structure of the new three-legged piano stool half-sandwich type complex. The ruthenium(II) ion is coordinated to a chloro ligand, a triphenylphosphine and a tethered η⁶-(phenyl-p-O-methoxy) κ¹-P N-diphenylphosphino N'-diisopropyl amidine ligand. The ruthenium adopts a pseudo-tetrahedral geometry with the P1—Ru1—Cl1, P1—Ru1—Cl2, and Cl2—Ru1—Cl1 bond angles close to 90 °. As expected, the carbon atoms of the η⁶-coordinated ring are coplanar. It is proposed that there are π-π intramolecular arene interactions between the phenyl ring (C14, C15, C16, C17, C18, C19) coordinated to P1 and the phenyl ring (C39, C40, C41, C42, C43, C44) on P2. The distance beween the centroids of the two rings is 3.609 Å, their average interplane distance is 3.397 Å and their offset angle α is 19.9 °. The title complex was fully characterized by infrared spectroscopy, ¹H, ¹³C and ³¹P NMR spectroscopy, together with mass spectrometry. The formation of the title compound opens up a synthetic route for the preparation of a large variety of tethered three-legged piano stool, half-sandwich functionalized η⁶-arene ruthenium(II) complexes, which will be tested both as catalysts and anticancer drugs. Currently, η⁶-arene ruthenium-based anticancer chemotherapies are making significant advances in clinical trials.

Related literature top

For related tethered η⁶-arene ruthenium(II) half-sandwich piano-stool complexes, see: Therrien & Ward (1999); Faller & D'Alliessi (2003); Cetinkaya et al. (2003); Cadierno et al. (2004); Ito et al. (2008); Arquier et al. (2009); Parekh et al. (2012). For η⁵-arene ruthenium(II) half-sandwich piano-stool complexes, see: Cole-Hamilton et al. (1976); Rosete et al. (1979); Snelgrove et al. (2005); Ferrando-Miguel et al. (2005). For the increasing medicinal interest in η⁶-arene ruthenium(II) half-sandwich complexes, see: Hartinger & Dyson (2009); Allardyce et al. (2001); Scolaro et al. (2005); Dyson (2007); Chatterjee et al. (2008).

For related literature, see: Kechaou et al. (2013).

Experimental top

All manipulations were carried out in dry solvents and under dry argon atmosphere. The precursor complex [RuCl(PPh3)(η⁵:κ¹-OC₆H₄C(NiPr₂)=N-PPh₂)] was prepared according to the previously described experimental procedure of Kechaou et al.(2013). Methyl trifluoromethanesulfonate was purchased from Aldrich and used as received without further purification. Methyl trifluoromethanesulfonate (0.025 ml; 0.230 mmol; 1 eq) was added at room temperature on the precursor complex [RuCl(PPh₃)(η⁵:κ¹-OC₆H₄C(NiPr₂)=N-PPh₂)] (0.185 g; 0.230 mmol) dissolved in dichloromethane (15 ml) using standard Schlenk-line and cannula techniques under dry argon atmosphere. The reaction mixture was stirred for 2 h at room temperature. After removal of the volatiles, the residue was washed with 2 x 15 ml of ether and dried under vacuum to give a dark-yellow powder of the title compound [RuCl(PPh₃)(η⁶:κ¹-MeOC₆H₄C(NiPr₂)=N-PPh₂)] (OSO₂CF₃)(0.200 mg, 90% isolated yield). Dissolution of 30 mg of the resulting dark yellow powder in 0.5 ml of dry acetone followed by careful diffusion of pentane as a non solvent into the resulting solution afforded at room temperature, crystals of the title compound suitable for XRD analysis.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2010); cell refinement: CrysAlis CCD (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

Figures top

Fig. 1. A molecule of the title complex with atom labelling scheme and 30% probability displacement ellipsoids.

Chlorido(η⁶-N²-diphenylphosphanyl-N¹,N¹-diisopropyl-4-methoxybenzamidine-κP)(triphenylphosphane-κP)ruthenium(II) trifluoromethansulfonate acetone disolvate top

Crystal data top

[RuCl(C₁₈H₁₅P)(C₂₆H₃₁N₂OP)](CF₃O₃S)·2C₃H₆O	F(000) = 2240
M_r = 1082.51	D_x = 1.394 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14433 reflections
a = 11.6970 (2) Å	θ = 3.3–29.1°
b = 15.0260 (3) Å	µ = 0.52 mm⁻¹
c = 29.7770 (6) Å	T = 180 K
β = 99.864 (2)°	Parallelepiped, yellow
V = 5156.21 (17) Å³	0.19 × 0.1 × 0.03 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer	10532 independent reflections
Graphite monochromator	8192 reflections with I > 2σ(I)
Detector resolution: 16.1978 pixels mm^-1	R_int = 0.046
ω scans	θ_max = 26.4°, θ_min = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	h = −14→14
T_min = 0.933, T_max = 0.982	k = −18→18
43527 measured reflections	l = −37→36

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0251P)² + 6.3129P] where P = (F_o² + 2F_c²)/3
10532 reflections	(Δ/σ)_max = 0.001
608 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[RuCl(C₁₈H₁₅P)(C₂₆H₃₁N₂OP)](CF₃O₃S)·2C₃H₆O	V = 5156.21 (17) Å³
M_r = 1082.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6970 (2) Å	µ = 0.52 mm⁻¹
b = 15.0260 (3) Å	T = 180 K
c = 29.7770 (6) Å	0.19 × 0.1 × 0.03 mm
β = 99.864 (2)°

Data collection top

Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer	10532 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	8192 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.982	R_int = 0.046
43527 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.09	Δρ_max = 0.49 e Å⁻³
10532 reflections	Δρ_min = −0.37 e Å⁻³
608 parameters

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
C1	0.7448 (2)	0.64736 (19)	0.33547 (10)	0.0191 (6)
C2	0.9016 (3)	0.5770 (2)	0.38976 (11)	0.0304 (7)
H2	0.94	0.5174	0.3911	0.036*
C3	0.8536 (3)	0.5865 (3)	0.43390 (11)	0.0438 (9)
H3A	0.7945	0.5407	0.4351	0.066*
H3B	0.8187	0.6456	0.4351	0.066*
H3C	0.9167	0.5793	0.4599	0.066*
C4	0.9954 (3)	0.6449 (3)	0.38473 (14)	0.0451 (10)
H4A	1.0228	0.6349	0.3558	0.068*
H4B	1.0604	0.6383	0.4101	0.068*
H4C	0.9633	0.7051	0.3851	0.068*
C5	0.7945 (3)	0.4909 (2)	0.32253 (10)	0.0258 (7)
H5	0.7267	0.4988	0.2974	0.031*
C6	0.9004 (3)	0.4730 (2)	0.30033 (13)	0.0407 (9)
H6A	0.9139	0.5241	0.2814	0.061*
H6B	0.8869	0.4196	0.2812	0.061*
H6C	0.9686	0.4638	0.324	0.061*
C7	0.7657 (3)	0.4149 (2)	0.35213 (12)	0.0344 (8)
H7A	0.6966	0.4301	0.3651	0.052*
H7B	0.8312	0.4045	0.3769	0.052*
H7C	0.7506	0.3609	0.3336	0.052*
C8	0.6649 (2)	0.64521 (18)	0.28973 (9)	0.0175 (6)
C9	0.5538 (2)	0.60572 (18)	0.28247 (10)	0.0185 (6)
H9	0.5249	0.575	0.3082	0.022*
C10	0.4784 (3)	0.61740 (18)	0.23983 (10)	0.0205 (6)
H10	0.395	0.6004	0.2374	0.025*
C11	0.5109 (3)	0.66996 (19)	0.20556 (9)	0.0204 (6)
C12	0.6224 (2)	0.71251 (19)	0.21369 (10)	0.0201 (6)
H12	0.6403	0.76	0.1924	0.024*
C13	0.7009 (2)	0.69499 (18)	0.25352 (9)	0.0192 (6)
H13	0.7749	0.7296	0.2599	0.023*
C14	0.6426 (2)	0.86642 (18)	0.38598 (10)	0.0191 (6)
C15	0.6010 (3)	0.95355 (19)	0.38091 (11)	0.0242 (7)
H15	0.5835	0.9793	0.3514	0.029*
C16	0.5853 (3)	1.0024 (2)	0.41863 (12)	0.0326 (8)
H16	0.5574	1.0618	0.4151	0.039*
C17	0.6101 (3)	0.9647 (2)	0.46174 (12)	0.0354 (8)
H17	0.5991	0.9986	0.4876	0.042*
C18	0.6506 (3)	0.8787 (2)	0.46733 (11)	0.0345 (8)
H18	0.6674	0.8532	0.4969	0.041*
C19	0.6669 (3)	0.8291 (2)	0.42919 (10)	0.0269 (7)
H19	0.6947	0.7697	0.4329	0.032*
C20	0.7844 (2)	0.88336 (18)	0.32068 (10)	0.0205 (6)
C21	0.7796 (3)	0.9194 (2)	0.27773 (11)	0.0277 (7)
H21	0.7153	0.9072	0.2544	0.033*
C22	0.8695 (3)	0.9736 (2)	0.26888 (13)	0.0389 (9)
H22	0.8669	0.9983	0.2393	0.047*
C23	0.9623 (3)	0.9917 (2)	0.30272 (13)	0.0386 (9)
H23	1.0229	1.0293	0.2964	0.046*
C24	0.9680 (3)	0.9559 (2)	0.34557 (13)	0.0385 (9)
H24	1.0325	0.9683	0.3687	0.046*
C25	0.8796 (3)	0.9019 (2)	0.35462 (11)	0.0311 (7)
H25	0.8834	0.877	0.3842	0.037*
C26	0.4576 (3)	0.7429 (2)	0.13336 (11)	0.0361 (8)
H26A	0.3943	0.7423	0.1071	0.054*
H26B	0.5305	0.7271	0.1233	0.054*
H26C	0.4644	0.8025	0.1469	0.054*
C27	0.2384 (2)	0.75490 (18)	0.27688 (9)	0.0189 (6)
C28	0.2233 (3)	0.73245 (18)	0.23098 (10)	0.0221 (6)
H28	0.2892	0.7226	0.2169	0.027*
C29	0.1127 (3)	0.72436 (19)	0.20550 (10)	0.0259 (7)
H29	0.1033	0.7086	0.1742	0.031*
C30	0.0166 (3)	0.7391 (2)	0.22557 (11)	0.0294 (7)
H30	−0.0591	0.7333	0.2082	0.035*
C31	0.0305 (3)	0.7624 (2)	0.27103 (11)	0.0291 (7)
H31	−0.0358	0.7735	0.2847	0.035*
C32	0.1399 (3)	0.76975 (19)	0.29674 (11)	0.0246 (7)
H32	0.1485	0.785	0.3281	0.029*
C33	0.3814 (2)	0.65650 (18)	0.34787 (10)	0.0192 (6)
C34	0.4756 (3)	0.6391 (2)	0.38184 (10)	0.0239 (7)
H34	0.5316	0.6842	0.3909	0.029*
C35	0.4885 (3)	0.5561 (2)	0.40268 (11)	0.0327 (8)
H35	0.5533	0.5445	0.4259	0.039*
C36	0.4065 (3)	0.4902 (2)	0.38956 (12)	0.0391 (9)
H36	0.4157	0.4332	0.4035	0.047*
C37	0.3121 (3)	0.5075 (2)	0.35641 (13)	0.0408 (9)
H37	0.2559	0.4623	0.3476	0.049*
C38	0.2983 (3)	0.59039 (19)	0.33575 (11)	0.0271 (7)
H38	0.232	0.6021	0.3133	0.033*
C39	0.3551 (2)	0.84996 (18)	0.35094 (10)	0.0179 (6)
C40	0.3472 (3)	0.8362 (2)	0.39642 (10)	0.0245 (7)
H40	0.3655	0.7796	0.41	0.029*
C41	0.3125 (3)	0.9056 (2)	0.42219 (11)	0.0323 (8)
H41	0.3073	0.8958	0.4533	0.039*
C42	0.2858 (3)	0.9876 (2)	0.40318 (12)	0.0317 (8)
H42	0.262	1.0344	0.4209	0.038*
C43	0.2936 (3)	1.0015 (2)	0.35794 (11)	0.0296 (7)
H43	0.2751	1.0583	0.3447	0.035*
C44	0.3281 (3)	0.93381 (19)	0.33178 (11)	0.0246 (7)
H44	0.3334	0.9443	0.3007	0.03*
C50	0.8526 (4)	0.6788 (3)	0.56855 (15)	0.0553 (11)
C66	0.6369 (3)	0.3577 (3)	0.48420 (13)	0.0424 (9)
C67	0.7339 (4)	0.3712 (3)	0.52314 (14)	0.0592 (12)
H67A	0.7881	0.4154	0.5147	0.089*
H67B	0.7747	0.3147	0.5306	0.089*
H67C	0.7027	0.3924	0.5497	0.089*
C68	0.5406 (4)	0.2982 (3)	0.49175 (13)	0.0580 (12)
H68A	0.4793	0.2993	0.4648	0.087*
H68B	0.5092	0.3186	0.5184	0.087*
H68C	0.5698	0.2372	0.497	0.087*
C69	0.8491 (5)	0.1454 (4)	0.4658 (2)	0.0786 (16)
C70	0.8658 (6)	0.1162 (6)	0.4222 (3)	0.175 (5)
H70A	0.8907	0.0538	0.424	0.263*
H70B	0.9254	0.1528	0.4118	0.263*
H70C	0.7928	0.1216	0.4007	0.263*
C71	0.9401 (7)	0.1297 (7)	0.5068 (3)	0.190 (5)
H71A	1.0076	0.1674	0.505	0.285*
H71B	0.9636	0.0671	0.5078	0.285*
H71C	0.9089	0.1444	0.5344	0.285*
N1	0.7535 (2)	0.72111 (15)	0.35940 (8)	0.0198 (5)
N2	0.8092 (2)	0.57553 (15)	0.34877 (8)	0.0213 (5)
O1	0.43348 (18)	0.67901 (14)	0.16692 (7)	0.0263 (5)
O2	0.7757 (2)	0.70212 (17)	0.64312 (8)	0.0464 (7)
O3	0.8895 (2)	0.81958 (17)	0.61752 (9)	0.0490 (7)
O4	0.6950 (2)	0.79177 (18)	0.57825 (9)	0.0502 (7)
O5	0.7618 (4)	0.1818 (3)	0.47194 (14)	0.1011 (13)
O6	0.6368 (3)	0.3922 (2)	0.44746 (10)	0.0660 (9)
P1	0.67390 (6)	0.80800 (5)	0.33617 (2)	0.01691 (15)
P2	0.38071 (6)	0.75812 (5)	0.31383 (2)	0.01565 (15)
S1	0.79746 (7)	0.75662 (6)	0.60604 (3)	0.02905 (17)
Cl1	0.47598 (6)	0.89077 (5)	0.24250 (3)	0.02359 (16)
Ru1	0.541225 (18)	0.750672 (15)	0.276075 (7)	0.01445 (6)
F1	0.9469 (3)	0.6396 (3)	0.58828 (13)	0.1238 (14)
F2	0.8779 (3)	0.7198 (2)	0.53197 (10)	0.0985 (11)
F3	0.7758 (3)	0.61686 (19)	0.55310 (11)	0.0963 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0157 (15)	0.0222 (15)	0.0200 (15)	0.0012 (11)	0.0046 (12)	0.0035 (12)
C2	0.0301 (18)	0.0293 (17)	0.0266 (17)	0.0070 (14)	−0.0094 (14)	0.0016 (14)
C3	0.056 (2)	0.048 (2)	0.0244 (19)	0.0118 (19)	−0.0037 (17)	0.0037 (16)
C4	0.0236 (19)	0.050 (2)	0.055 (2)	−0.0009 (16)	−0.0121 (17)	0.0023 (19)
C5	0.0280 (17)	0.0241 (16)	0.0236 (16)	0.0078 (13)	−0.0003 (13)	−0.0030 (13)
C6	0.049 (2)	0.0341 (19)	0.044 (2)	0.0098 (17)	0.0218 (19)	−0.0033 (17)
C7	0.042 (2)	0.0266 (17)	0.0345 (19)	−0.0002 (15)	0.0060 (16)	−0.0032 (15)
C8	0.0199 (15)	0.0151 (13)	0.0169 (14)	0.0050 (11)	0.0018 (12)	−0.0028 (11)
C9	0.0196 (15)	0.0146 (13)	0.0218 (15)	0.0036 (11)	0.0054 (12)	−0.0022 (12)
C10	0.0202 (16)	0.0174 (14)	0.0235 (16)	0.0007 (12)	0.0030 (13)	−0.0045 (12)
C11	0.0236 (16)	0.0217 (15)	0.0154 (14)	0.0044 (12)	0.0021 (12)	−0.0049 (12)
C12	0.0217 (15)	0.0215 (14)	0.0190 (15)	0.0016 (12)	0.0084 (12)	−0.0006 (12)
C13	0.0191 (15)	0.0178 (14)	0.0215 (15)	0.0011 (11)	0.0061 (12)	−0.0032 (12)
C14	0.0185 (15)	0.0201 (14)	0.0183 (15)	−0.0054 (12)	0.0023 (12)	−0.0045 (12)
C15	0.0250 (16)	0.0230 (15)	0.0254 (16)	−0.0038 (13)	0.0067 (13)	−0.0032 (13)
C16	0.0284 (18)	0.0292 (17)	0.041 (2)	−0.0048 (14)	0.0094 (16)	−0.0125 (15)
C17	0.0316 (19)	0.046 (2)	0.0299 (19)	−0.0055 (16)	0.0086 (15)	−0.0211 (16)
C18	0.0312 (19)	0.052 (2)	0.0202 (17)	−0.0044 (16)	0.0037 (14)	−0.0052 (15)
C19	0.0269 (17)	0.0304 (17)	0.0231 (16)	−0.0016 (14)	0.0031 (13)	−0.0014 (13)
C20	0.0163 (15)	0.0194 (14)	0.0271 (16)	−0.0002 (11)	0.0076 (13)	−0.0045 (12)
C21	0.0203 (16)	0.0284 (16)	0.0342 (18)	0.0007 (13)	0.0039 (14)	0.0056 (14)
C22	0.0297 (19)	0.039 (2)	0.049 (2)	−0.0015 (16)	0.0086 (17)	0.0215 (17)
C23	0.0243 (18)	0.0335 (19)	0.061 (3)	−0.0082 (15)	0.0157 (18)	0.0018 (18)
C24	0.0279 (19)	0.046 (2)	0.042 (2)	−0.0157 (16)	0.0072 (16)	−0.0125 (17)
C25	0.0250 (17)	0.044 (2)	0.0243 (17)	−0.0107 (15)	0.0038 (14)	−0.0059 (15)
C26	0.0392 (19)	0.046 (2)	0.0219 (16)	0.0074 (17)	0.0023 (14)	0.0078 (16)
C27	0.0176 (13)	0.0141 (13)	0.0241 (14)	−0.0003 (12)	0.0012 (11)	0.0016 (13)
C28	0.0212 (15)	0.0218 (16)	0.0236 (15)	0.0021 (12)	0.0044 (12)	0.0017 (12)
C29	0.0294 (17)	0.0260 (16)	0.0206 (16)	−0.0004 (13)	−0.0006 (13)	0.0016 (12)
C30	0.0169 (15)	0.0321 (18)	0.0364 (18)	−0.0040 (14)	−0.0038 (13)	0.0035 (15)
C31	0.0193 (15)	0.0329 (18)	0.0359 (18)	−0.0004 (13)	0.0067 (13)	−0.0024 (15)
C32	0.0211 (15)	0.0268 (17)	0.0261 (16)	−0.0025 (12)	0.0051 (13)	−0.0033 (13)
C33	0.0211 (15)	0.0182 (14)	0.0200 (15)	0.0014 (12)	0.0081 (12)	0.0021 (12)
C34	0.0244 (16)	0.0253 (16)	0.0218 (16)	−0.0017 (13)	0.0037 (13)	0.0028 (13)
C35	0.035 (2)	0.0354 (19)	0.0270 (18)	0.0088 (15)	0.0036 (15)	0.0093 (15)
C36	0.054 (2)	0.0227 (17)	0.041 (2)	0.0006 (16)	0.0093 (18)	0.0113 (15)
C37	0.047 (2)	0.0257 (18)	0.048 (2)	−0.0117 (16)	0.0049 (19)	0.0059 (16)
C38	0.0298 (18)	0.0222 (16)	0.0285 (17)	−0.0042 (13)	0.0029 (14)	0.0022 (13)
C39	0.0131 (14)	0.0195 (14)	0.0219 (15)	−0.0013 (11)	0.0049 (12)	−0.0042 (12)
C40	0.0284 (17)	0.0225 (15)	0.0228 (16)	−0.0016 (13)	0.0053 (13)	−0.0031 (13)
C41	0.040 (2)	0.0370 (19)	0.0218 (17)	−0.0055 (16)	0.0101 (15)	−0.0102 (14)
C42	0.0297 (18)	0.0280 (17)	0.038 (2)	0.0010 (14)	0.0091 (15)	−0.0142 (15)
C43	0.0321 (18)	0.0192 (15)	0.037 (2)	0.0043 (13)	0.0053 (15)	−0.0043 (14)
C44	0.0258 (17)	0.0241 (16)	0.0246 (16)	−0.0010 (13)	0.0062 (13)	0.0027 (13)
C50	0.065 (3)	0.052 (3)	0.054 (3)	0.012 (2)	0.025 (2)	−0.001 (2)
C66	0.048 (2)	0.045 (2)	0.032 (2)	0.0074 (18)	0.0013 (17)	0.0012 (17)
C67	0.055 (3)	0.071 (3)	0.047 (3)	−0.010 (2)	−0.003 (2)	−0.006 (2)
C68	0.049 (3)	0.087 (3)	0.036 (2)	−0.015 (2)	−0.0002 (19)	0.000 (2)
C69	0.085 (4)	0.060 (3)	0.099 (5)	−0.006 (3)	0.041 (4)	0.006 (3)
C70	0.124 (6)	0.267 (11)	0.164 (7)	−0.105 (7)	0.107 (6)	−0.131 (7)
C71	0.118 (7)	0.263 (13)	0.188 (10)	0.034 (8)	0.023 (7)	0.105 (9)
N1	0.0192 (13)	0.0201 (12)	0.0185 (12)	0.0007 (10)	−0.0012 (10)	−0.0019 (10)
N2	0.0218 (13)	0.0195 (12)	0.0205 (13)	0.0044 (10)	−0.0024 (11)	−0.0015 (10)
O1	0.0259 (12)	0.0333 (12)	0.0179 (11)	0.0001 (9)	−0.0014 (9)	−0.0020 (9)
O2	0.0642 (18)	0.0409 (15)	0.0380 (14)	−0.0084 (13)	0.0201 (13)	0.0028 (12)
O3	0.0382 (15)	0.0519 (16)	0.0543 (17)	−0.0170 (13)	0.0010 (13)	0.0013 (14)
O4	0.0375 (15)	0.0547 (16)	0.0525 (17)	0.0067 (13)	−0.0086 (13)	0.0005 (14)
O5	0.114 (3)	0.095 (3)	0.098 (3)	0.025 (3)	0.031 (3)	−0.019 (2)
O6	0.081 (2)	0.064 (2)	0.0507 (19)	0.0075 (17)	0.0058 (17)	0.0228 (16)
P1	0.0171 (4)	0.0170 (3)	0.0162 (4)	−0.0007 (3)	0.0016 (3)	−0.0014 (3)
P2	0.0156 (3)	0.0150 (3)	0.0165 (3)	−0.0006 (3)	0.0029 (3)	−0.0002 (3)
S1	0.0282 (4)	0.0303 (4)	0.0283 (4)	−0.0015 (4)	0.0040 (3)	0.0004 (4)
Cl1	0.0252 (4)	0.0190 (3)	0.0264 (4)	0.0033 (3)	0.0040 (3)	0.0059 (3)
Ru1	0.01440 (11)	0.01440 (10)	0.01446 (11)	0.00007 (9)	0.00221 (8)	−0.00016 (10)
F1	0.113 (3)	0.133 (3)	0.129 (3)	0.091 (2)	0.028 (2)	−0.004 (2)
F2	0.139 (3)	0.111 (2)	0.0626 (18)	−0.002 (2)	0.065 (2)	−0.0061 (17)
F3	0.139 (3)	0.0638 (18)	0.097 (2)	−0.0247 (19)	0.050 (2)	−0.0467 (17)

Geometric parameters (Å, º) top

C1—N1	1.312 (4)	C26—H26C	0.98
C1—N2	1.337 (4)	C27—C28	1.389 (4)
C1—C8	1.514 (4)	C27—C32	1.401 (4)
C2—N2	1.486 (4)	C27—P2	1.832 (3)
C2—C3	1.522 (5)	C28—C29	1.388 (4)
C2—C4	1.523 (5)	C28—H28	0.95
C2—H2	1	C29—C30	1.379 (4)
C3—H3A	0.98	C29—H29	0.95
C3—H3B	0.98	C30—C31	1.380 (4)
C3—H3C	0.98	C30—H30	0.95
C4—H4A	0.98	C31—C32	1.378 (4)
C4—H4B	0.98	C31—H31	0.95
C4—H4C	0.98	C32—H32	0.95
C5—N2	1.487 (4)	C33—C34	1.387 (4)
C5—C7	1.516 (4)	C33—C38	1.394 (4)
C5—C6	1.524 (4)	C33—P2	1.832 (3)
C5—H5	1	C34—C35	1.389 (4)
C6—H6A	0.98	C34—H34	0.95
C6—H6B	0.98	C35—C36	1.387 (5)
C6—H6C	0.98	C35—H35	0.95
C7—H7A	0.98	C36—C37	1.374 (5)
C7—H7B	0.98	C36—H36	0.95
C7—H7C	0.98	C37—C38	1.387 (4)
C8—C9	1.411 (4)	C37—H37	0.95
C8—C13	1.434 (4)	C38—H38	0.95
C8—Ru1	2.137 (3)	C39—C40	1.388 (4)
C9—C10	1.427 (4)	C39—C44	1.397 (4)
C9—Ru1	2.189 (3)	C39—P2	1.824 (3)
C9—H9	1	C40—C41	1.395 (4)
C10—C11	1.394 (4)	C40—H40	0.95
C10—Ru1	2.333 (3)	C41—C42	1.370 (5)
C10—H10	1	C41—H41	0.95
C11—O1	1.344 (3)	C42—C43	1.382 (5)
C11—C12	1.435 (4)	C42—H42	0.95
C11—Ru1	2.398 (3)	C43—C44	1.382 (4)
C12—C13	1.395 (4)	C43—H43	0.95
C12—Ru1	2.299 (3)	C44—H44	0.95
C12—H12	1	C50—F1	1.299 (5)
C13—Ru1	2.252 (3)	C50—F3	1.320 (5)
C13—H13	1	C50—F2	1.328 (5)
C14—C19	1.388 (4)	C50—S1	1.810 (4)
C14—C15	1.396 (4)	C66—O6	1.210 (4)
C14—P1	1.814 (3)	C66—C68	1.486 (5)
C15—C16	1.380 (4)	C66—C67	1.490 (5)
C15—H15	0.95	C67—H67A	0.98
C16—C17	1.388 (5)	C67—H67B	0.98
C16—H16	0.95	C67—H67C	0.98
C17—C18	1.377 (5)	C68—H68A	0.98
C17—H17	0.95	C68—H68B	0.98
C18—C19	1.398 (4)	C68—H68C	0.98
C18—H18	0.95	C69—O5	1.199 (6)
C19—H19	0.95	C69—C70	1.416 (8)
C20—C21	1.381 (4)	C69—C71	1.493 (9)
C20—C25	1.398 (4)	C70—H70A	0.98
C20—P1	1.836 (3)	C70—H70B	0.98
C21—C22	1.391 (4)	C70—H70C	0.98
C21—H21	0.95	C71—H71A	0.98
C22—C23	1.375 (5)	C71—H71B	0.98
C22—H22	0.95	C71—H71C	0.98
C23—C24	1.376 (5)	N1—P1	1.682 (2)
C23—H23	0.95	O2—S1	1.432 (2)
C24—C25	1.377 (4)	O3—S1	1.430 (2)
C24—H24	0.95	O4—S1	1.435 (3)
C25—H25	0.95	P1—Ru1	2.3240 (8)
C26—O1	1.448 (4)	P2—Ru1	2.3505 (7)
C26—H26A	0.98	Cl1—Ru1	2.3984 (7)
C26—H26B	0.98

N1—C1—N2	122.3 (3)	C31—C32—H32	119.8
N1—C1—C8	119.0 (2)	C27—C32—H32	119.8
N2—C1—C8	118.6 (2)	C34—C33—C38	119.1 (3)
N2—C2—C3	112.7 (3)	C34—C33—P2	119.2 (2)
N2—C2—C4	111.4 (3)	C38—C33—P2	120.9 (2)
C3—C2—C4	113.6 (3)	C33—C34—C35	120.5 (3)
N2—C2—H2	106.2	C33—C34—H34	119.8
C3—C2—H2	106.2	C35—C34—H34	119.8
C4—C2—H2	106.2	C36—C35—C34	119.8 (3)
C2—C3—H3A	109.5	C36—C35—H35	120.1
C2—C3—H3B	109.5	C34—C35—H35	120.1
H3A—C3—H3B	109.5	C37—C36—C35	120.0 (3)
C2—C3—H3C	109.5	C37—C36—H36	120
H3A—C3—H3C	109.5	C35—C36—H36	120
H3B—C3—H3C	109.5	C36—C37—C38	120.4 (3)
C2—C4—H4A	109.5	C36—C37—H37	119.8
C2—C4—H4B	109.5	C38—C37—H37	119.8
H4A—C4—H4B	109.5	C37—C38—C33	120.2 (3)
C2—C4—H4C	109.5	C37—C38—H38	119.9
H4A—C4—H4C	109.5	C33—C38—H38	119.9
H4B—C4—H4C	109.5	C40—C39—C44	119.0 (3)
N2—C5—C7	110.9 (2)	C40—C39—P2	121.6 (2)
N2—C5—C6	110.5 (3)	C44—C39—P2	118.9 (2)
C7—C5—C6	113.4 (3)	C39—C40—C41	120.0 (3)
N2—C5—H5	107.3	C39—C40—H40	120
C7—C5—H5	107.3	C41—C40—H40	120
C6—C5—H5	107.3	C42—C41—C40	120.8 (3)
C5—C6—H6A	109.5	C42—C41—H41	119.6
C5—C6—H6B	109.5	C40—C41—H41	119.6
H6A—C6—H6B	109.5	C41—C42—C43	119.4 (3)
C5—C6—H6C	109.5	C41—C42—H42	120.3
H6A—C6—H6C	109.5	C43—C42—H42	120.3
H6B—C6—H6C	109.5	C42—C43—C44	120.8 (3)
C5—C7—H7A	109.5	C42—C43—H43	119.6
C5—C7—H7B	109.5	C44—C43—H43	119.6
H7A—C7—H7B	109.5	C43—C44—C39	120.0 (3)
C5—C7—H7C	109.5	C43—C44—H44	120
H7A—C7—H7C	109.5	C39—C44—H44	120
H7B—C7—H7C	109.5	F1—C50—F3	108.2 (4)
C9—C8—C13	119.1 (3)	F1—C50—F2	106.8 (4)
C9—C8—C1	123.8 (2)	F3—C50—F2	106.0 (4)
C13—C8—C1	116.7 (2)	F1—C50—S1	112.2 (3)
C9—C8—Ru1	72.97 (16)	F3—C50—S1	112.2 (3)
C13—C8—Ru1	75.33 (16)	F2—C50—S1	111.1 (3)
C1—C8—Ru1	116.66 (18)	O6—C66—C68	120.7 (4)
C8—C9—C10	119.8 (3)	O6—C66—C67	121.9 (4)
C8—C9—Ru1	68.97 (15)	C68—C66—C67	117.4 (3)
C10—C9—Ru1	77.18 (16)	C66—C67—H67A	109.5
C8—C9—H9	120	C66—C67—H67B	109.5
C10—C9—H9	120	H67A—C67—H67B	109.5
Ru1—C9—H9	120	C66—C67—H67C	109.5
C11—C10—C9	121.1 (3)	H67A—C67—H67C	109.5
C11—C10—Ru1	75.44 (16)	H67B—C67—H67C	109.5
C9—C10—Ru1	66.20 (15)	C66—C68—H68A	109.5
C11—C10—H10	118.6	C66—C68—H68B	109.5
C9—C10—H10	118.6	H68A—C68—H68B	109.5
Ru1—C10—H10	118.6	C66—C68—H68C	109.5
O1—C11—C10	117.1 (3)	H68A—C68—H68C	109.5
O1—C11—C12	124.0 (3)	H68B—C68—H68C	109.5
C10—C11—C12	118.9 (3)	O5—C69—C70	122.4 (7)
O1—C11—Ru1	132.48 (19)	O5—C69—C71	117.0 (6)
C10—C11—Ru1	70.33 (16)	C70—C69—C71	120.6 (7)
C12—C11—Ru1	68.49 (15)	C69—C70—H70A	109.5
C13—C12—C11	120.4 (3)	C69—C70—H70B	109.5
C13—C12—Ru1	70.31 (15)	H70A—C70—H70B	109.5
C11—C12—Ru1	76.01 (16)	C69—C70—H70C	109.5
C13—C12—H12	119.6	H70A—C70—H70C	109.5
C11—C12—H12	119.6	H70B—C70—H70C	109.5
Ru1—C12—H12	119.6	C69—C71—H71A	109.5
C12—C13—C8	120.2 (3)	C69—C71—H71B	109.5
C12—C13—Ru1	74.01 (16)	H71A—C71—H71B	109.5
C8—C13—Ru1	66.65 (15)	C69—C71—H71C	109.5
C12—C13—H13	119	H71A—C71—H71C	109.5
C8—C13—H13	119	H71B—C71—H71C	109.5
Ru1—C13—H13	119	C1—N1—P1	116.5 (2)
C19—C14—C15	119.4 (3)	C1—N2—C2	121.7 (2)
C19—C14—P1	121.7 (2)	C1—N2—C5	121.8 (2)
C15—C14—P1	118.7 (2)	C2—N2—C5	116.5 (2)
C16—C15—C14	120.2 (3)	C11—O1—C26	118.4 (2)
C16—C15—H15	119.9	N1—P1—C14	102.38 (13)
C14—C15—H15	119.9	N1—P1—C20	102.62 (13)
C15—C16—C17	120.0 (3)	C14—P1—C20	98.99 (13)
C15—C16—H16	120	N1—P1—Ru1	106.16 (9)
C17—C16—H16	120	C14—P1—Ru1	127.40 (10)
C18—C17—C16	120.5 (3)	C20—P1—Ru1	116.18 (10)
C18—C17—H17	119.7	C39—P2—C27	99.05 (13)
C16—C17—H17	119.7	C39—P2—C33	106.32 (13)
C17—C18—C19	119.6 (3)	C27—P2—C33	103.16 (13)
C17—C18—H18	120.2	C39—P2—Ru1	123.58 (9)
C19—C18—H18	120.2	C27—P2—Ru1	115.43 (9)
C14—C19—C18	120.2 (3)	C33—P2—Ru1	107.27 (9)
C14—C19—H19	119.9	O3—S1—O2	114.85 (16)
C18—C19—H19	119.9	O3—S1—O4	114.49 (17)
C21—C20—C25	119.5 (3)	O2—S1—O4	114.44 (17)
C21—C20—P1	123.8 (2)	O3—S1—C50	103.96 (19)
C25—C20—P1	116.7 (2)	O2—S1—C50	103.62 (18)
C20—C21—C22	119.5 (3)	O4—S1—C50	103.45 (19)
C20—C21—H21	120.2	C8—Ru1—C9	38.06 (10)
C22—C21—H21	120.2	C8—Ru1—C13	38.02 (10)
C23—C22—C21	120.3 (3)	C9—Ru1—C13	67.02 (10)
C23—C22—H22	119.9	C8—Ru1—C12	66.99 (10)
C21—C22—H22	119.9	C9—Ru1—C12	77.96 (10)
C22—C23—C24	120.6 (3)	C13—Ru1—C12	35.68 (10)
C22—C23—H23	119.7	C8—Ru1—P1	77.72 (8)
C24—C23—H23	119.7	C9—Ru1—P1	106.01 (8)
C23—C24—C25	119.5 (3)	C13—Ru1—P1	83.61 (8)
C23—C24—H24	120.2	C12—Ru1—P1	113.63 (8)
C25—C24—H24	120.2	C8—Ru1—C10	66.47 (10)
C24—C25—C20	120.5 (3)	C9—Ru1—C10	36.61 (10)
C24—C25—H25	119.7	C13—Ru1—C10	75.79 (10)
C20—C25—H25	119.7	C12—Ru1—C10	63.45 (10)
O1—C26—H26A	109.5	P1—Ru1—C10	142.20 (7)
O1—C26—H26B	109.5	C8—Ru1—P2	120.95 (8)
H26A—C26—H26B	109.5	C9—Ru1—P2	93.03 (7)
O1—C26—H26C	109.5	C13—Ru1—P2	158.72 (7)
H26A—C26—H26C	109.5	C12—Ru1—P2	150.77 (8)
H26B—C26—H26C	109.5	P1—Ru1—P2	95.56 (3)
C28—C27—C32	118.6 (3)	C10—Ru1—P2	92.76 (7)
C28—C27—P2	123.2 (2)	C8—Ru1—C11	77.60 (10)
C32—C27—P2	118.1 (2)	C9—Ru1—C11	64.57 (10)
C29—C28—C27	120.6 (3)	C13—Ru1—C11	63.67 (10)
C29—C28—H28	119.7	C12—Ru1—C11	35.50 (10)
C27—C28—H28	119.7	P1—Ru1—C11	147.21 (7)
C30—C29—C28	120.1 (3)	C10—Ru1—C11	34.23 (10)
C30—C29—H29	120	P2—Ru1—C11	115.64 (7)
C28—C29—H29	120	C8—Ru1—Cl1	152.47 (8)
C29—C30—C31	119.8 (3)	C9—Ru1—Cl1	157.13 (8)
C29—C30—H30	120.1	C13—Ru1—Cl1	115.01 (7)
C31—C30—H30	120.1	C12—Ru1—Cl1	91.60 (7)
C32—C31—C30	120.5 (3)	P1—Ru1—Cl1	96.80 (3)
C32—C31—H31	119.7	C10—Ru1—Cl1	120.54 (7)
C30—C31—H31	119.7	P2—Ru1—Cl1	86.24 (3)
C31—C32—C27	120.4 (3)	C11—Ru1—Cl1	95.17 (7)

Experimental details

Crystal data
Chemical formula	[RuCl(C₁₈H₁₅P)(C₂₆H₃₁N₂OP)](CF₃O₃S)·2C₃H₆O
M_r	1082.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	180
a, b, c (Å)	11.6970 (2), 15.0260 (3), 29.7770 (6)
β (°)	99.864 (2)
V (Å³)	5156.21 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.19 × 0.1 × 0.03

Data collection
Diffractometer	Oxford Diffraction Xcalibur (Eos, Gemini ultra) diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.933, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	43527, 10532, 8192
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.089, 1.09
No. of reflections	10532
No. of parameters	608
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.37

Computer programs: CrysAlis CCD (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX publication routines (Farrugia, 2012).

Acknowledgements

We thank the French Ministry of Education for a PhD Fellowship for M-KP and the CNRS for financial support. Johnson Matthey is gratefully acknowledged for the loan of RuCl₃·xH₂O.

References

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