Chlorido(η(6)-N (2)-diphenylphosphanyl-N (1),N (1)-diisopropyl-4-methoxybenz-amidine-κP)(triphenylphosphane-κP)ruthenium(II) trifluoromethansulfonate acetone disolvate.

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 tri-phenyl-phosphine and a tethered η(6)-(phenyl-p-O-meth-oxy) κ(1)-P N-di-phenyl-phosphino N'-diisopropyl amidine ligand charge-balanced by a trifluormethansulfonate counter-anion. The η(6)-coordination mode of the arene incorporated into the structure was generated in situ after addition of methyl tri-fluoro-methane-sulfonate to the neutral η(5)-arene tethered precursor complex [RuCl(PPh3)(η(5):κ(1)-OC6H4C(NiPr2)=N-PPh2)] in di-chloro-methane solution.

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 = 1082.51

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.089

S = 1.09

10532 reflections

608 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis CCD; 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813029450/cq2007sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813029450/cq2007Isup3.cdx

968713

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[RuCl(C18H15P)(C26H31N2OP)](CF3O3S)·2C3H6O	F(000) = 2240
Mr = 1082.51	Dx = 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

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	Rint = 0.046
ω scans	θmax = 26.4°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	h = −14→14
Tmin = 0.933, Tmax = 0.982	k = −18→18
43527 measured reflections	l = −37→36

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(Fo2) + (0.0251P)2 + 6.3129P] where P = (Fo2 + 2Fc2)/3
10532 reflections	(Δ/σ)max = 0.001
608 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)