(Acetonitrile-κN){1,2-bis­[bis­(penta­fluoro­phenyl)phosphino]ethane-κ2P,P}(η5-penta­methyl­cyclo­penta­dien­yl)ruthenium(II) hexa­fluoro­phosphate

Bellabarba, R.M.; Nieuwenhuyzen, M.; Saunders, G.C.

doi:10.1107/S1600536805020052

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 8| August 2005| Pages m1588-m1589

https://doi.org/10.1107/S1600536805020052

(Acetonitrile-κN){1,2-bis[bis(pentafluorophenyl)phosphino]ethane-κ²P,P}(η⁵-pentamethylcyclopentadienyl)ruthenium(II) hexafluorophosphate

Ronan M. Bellabarba,^a Mark Nieuwenhuyzen ^a and Graham C. Saunders ^a ^*

^aSchool of Chemistry, Queen's University Belfast, David Keir Building, Belfast BT9 5AG, Northern Ireland
^*Correspondence e-mail: g.saunders@qub.ac.uk

(Received 26 April 2005; accepted 24 June 2005; online 16 July 2005)

The cation of the title salt, [Ru(η⁵-C₅Me₅)(NCMe){(C₆F₅)₂PCH₂CH₂P(C₆F₅)₂}]PF₆ or [Ru(C₁₀H₁₅)(C₂₆H₄F₂₀P₂)(C₂H₃N)]PF₆, has contacts with three anions. One lies close to the pentamethylcyclopentadienyl ring, such that three F atoms of the anion are ca 3.5 Å from two of the ring methyl C atoms of the cation and there is one H⋯F distance shorter than the sum of the van der Waals radii.

Comment

Salts of the cation [(η⁵-C₅Me₅)RhCl{(C₆F₅)₂PCH₂CH₂P(C₆F₅)₂}]⁺ have been found to undergo intramolecular dehydrofluorinative C–C reactions on thermolysis or in the presence of a proton sponge or fluoride, to yield [{η⁵,κP,κP-C₅Me₄CH₂C₆F₄-2-P(C₆F₅)CH₂CH₂P(C₆F₅)₂}RhCl]⁺ and then [{η⁵,κP,κP-C₅Me₃[CH₂C₆F₄-2-P(C₆F₅)CH₂]-1,3}RhCl]⁺ (Atherton et al., 1996 ; Bellabarba et al., 2001 ). The thermolysis is dependent on the solvent and the anion. The reaction for the tetrafluoroborate salt occurs only in polar protic solvents, such as ethanol, whereas for chloride, hexafluorophosphate and tetraphenylborate salts, the reaction also occurs readily in non-polar aprotic solvents, such as benzene (Atherton et al., 1999 ).

The structure of [(η⁵-C₅Me₅)RhCl{(C₆F₅)₂PCH₂CH₂P(C₆F₅)₂}]BF₄ revealed that a tetrafluoroborate anion is positioned close to the pentamethylcyclopentadienyl ligand, such that three F atoms of the anion form a plane almost parallel (5.1° deviation) to the C₅ plane, with a separation between the two planes of ca 3.19 Å. The anion is displaced slightly from the (η⁵-C₅Me₅)–Rh axis, giving rise to short F⋯H and F⋯C distances between the anion and the pentamethylcyclopentadienyl ligand of 2.4–2.7 and 3.1–3.3 Å, respectively (Atherton et al., 1996). A similar positioning of the anion and cation is found in the related salts [(η⁵-C₅Me₅)IrCl{(C₆F₅)₂PCH₂CH₂P(C₆F₅)₂}]BF₄ (Atherton et al., 1996) and [(η⁵-C₅Me₅)RhCl{(C₆H₃F₂-2,6)₂PCH₂CH₂P(C₆H₃F₂-2,6)₂}]BF₄ (Fawcett et al., 1998 ). If BF₄⁻⋯C₅Me₅ interactions are present in aprotic solvents, then the absence of similar anion⋯C₅Me₅ interactions in the salts of the other anions may provide the basis for an explanation for the difference in reactivity. Of particular relevance is the salt of the hexafluorophosphate anion, which is the most similar to the tetrafluoroborate anion. These two anions comprise a periphery of F atoms, with equilateral triangular faces with edges of ca 2.1–2.3 Å (Allen et al., 1987 ; Atherton et al., 1996; Fawcett et al., 1998). Unfortunately, crystals suitable for single-crystal X-ray diffraction studies of the non-tetrafluoroborate salts of [(η⁵-C₅Me₅)RhCl{(C₆F₅)₂PCH₂CH₂P(C₆F₅)₂}]⁺ have been elusive. However, the structure of the title isoelectronic ruthenium salt, [(η⁵-C₅Me₅)Ru(NCMe){(C₆F₅)₂PCH₂CH₂P(C₆F₅)₂}]PF₆, (I), has now been determined and is presented here.

The structure of (I) (Fig. 1) reveals that the hexafluorophosphate anion does not adopt a similar position to that of the tetrafluoroborate anion in [(η⁵-C₅Me₅)RhCl{(C₆F₅)₂PCH₂CH₂P(C₆F₅)₂}]BF₄ and [(η⁵-C₅Me₅)RhCl{(C₆H₃F₂-2,6)₂PCH₂CH₂P(C₆H₃F₂-2,6)₂}]BF₄. The cation shows contacts to three anions which are shorter than the sum of the van der Waals radii of the respective atoms. One anion position is close to the pentamethylcyclopentadienyl ligand, such that there is one F⋯H distance shorter than the sum of the van der Waals radii (F36⋯H10C = 2.626 Å). The shortest inter-ion F⋯C(C₅Me₅) distances are between atoms F34 and C9 [3.493 (6) Å], F36 and C10 [3.564 (7) Å], and F32 and C10 [3.597 (7) Å]. However, for this anion, the shortest inter-ion F⋯C distance of 3.028 (6) Å is between atoms F36 and C2S of the acetonitrile. The distance between atoms C3S and F36 is 3.123 (5) Å, with F36⋯H3S2 = 2.609 Å, and that between atoms C3S and F34 is 3.396 (7) Å, with F34⋯H3S2 = 2.481 Å.

Another anion position gives three short contacts with a C₆F₅ ring (F32⋯F26B = 2.888 (6) Å, F32⋯C26B = 2.964 (6) Å and F32⋯C25B = 3.110 (6) Å) and a contact with a CH₂ H atom (F35⋯H2A2 = 2.633 Å). The third anion position gives a contact with a C₆F₅ ring (F31⋯C14B = 3.113 (7) Å), a CH₂ H atom (F33⋯H1A1 = 2.599 Å) and an acetonitrile H atom (F35⋯H3S1 = 2.428 Å).

Figure 1
A view of (I)

. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

Experimental

The title complex was obtained from the reaction of [(η⁵-C₅Me₅)Ru(NCMe)₃]PF₆ with (C₆F₅)₂PCH₂CH₂P(C₆F₅)₂ in dichloromethane (10 ml) gave a yellow–green solution from which a small number of yellow crystals of (I) were obtained by cooling the reaction mixture to 273 K.

Crystal data

[Ru(C₁₀H₁₅)(C₂₆H₄F₂₀P₂)(C₂H₃N)]PF₆
M_r = 1180.55
Monoclinic, P 2₁ /n
a = 12.5380 (9) Å
b = 10.6157 (8) Å
c = 31.760 (2) Å
β = 98.062 (2)°
V = 4185.4 (5) Å³
Z = 4
D_x = 1.874 Mg m⁻³
Mo Kα radiation
Cell parameters from 5351 reflections
θ = 4–50°
μ = 0.64 mm⁻¹
T = 153 (2) K
Needle, red
0.42 × 0.10 × 0.08 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 1996 )T_min = 0.775, T_max = 0.951
37499 measured reflections
9479 independent reflections
5575 reflections with I > 2σ(I)
R_int = 0.098
θ_max = 27.5°
h = −16 → 16
k = −13 → 13
l = −41 → 40

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.109
S = 0.94
9479 reflections
627 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0422P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.83 e Å⁻³

H atoms were added in idealized positions and a riding model with fixed displacement parameters [U_iso(H) = 1.2U_eq of the parent atom (1.5U_eq for methyl H atoms].

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2002 ); data reduction: SHELXTL (Bruker, 2001) and SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536805020052/wk6052sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805020052/wk6052Isup2.hkl

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SHELXTL (Bruker, 2001) and SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(Acetonitrile-κN){1,2-bis[bis(pentafluorophenyl)phosphino]ethane- κ²P,P}(η⁵-pentamethylcyclopentadienyl)ruthenium(II) hexafluorophosphate top

Crystal data top

[Ru(C₁₀H₁₅)(C₂₆H₄F₂₀P₂)(C₂H₃N)]PF₆	F(000) = 2320
M_r = 1180.55	D_x = 1.874 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.5380 (9) Å	Cell parameters from 5351 reflections
b = 10.6157 (8) Å	θ = 4–50°
c = 31.760 (2) Å	µ = 0.64 mm⁻¹
β = 98.062 (2)°	T = 153 K
V = 4185.4 (5) Å³	Needle, red
Z = 4	0.42 × 0.10 × 0.08 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	9479 independent reflections
Radiation source: fine-focus sealed tube	5575 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
φ and ω scans	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.775, T_max = 0.951	k = −13→13
37499 measured reflections	l = −41→40

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)] = 0.047	Hydrogen site location: geom and difmap for Me H
wR(F²) = 0.109	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0422P)²] where P = (F_o² + 2F_c²)/3
9479 reflections	(Δ/σ)_max < 0.001
627 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.83 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Ru1	0.11895 (3)	0.13441 (3)	0.386595 (10)	0.02476 (9)
C1	0.1383 (4)	0.0814 (4)	0.45544 (13)	0.0344 (10)
C2	0.0259 (3)	0.0940 (4)	0.44016 (13)	0.0338 (10)
C3	−0.0011 (3)	0.0004 (4)	0.40794 (13)	0.0334 (10)
C4	0.0929 (3)	−0.0680 (4)	0.40313 (13)	0.0326 (10)
C5	0.1810 (3)	−0.0172 (4)	0.43183 (13)	0.0310 (10)
C6	0.1987 (4)	0.1406 (4)	0.49471 (13)	0.0426 (11)
H6A	0.1538	0.2057	0.5053	0.064*
H6B	0.2653	0.1788	0.4878	0.064*
H6C	0.2163	0.0760	0.5166	0.064*
C7	−0.0529 (4)	0.1709 (4)	0.46049 (15)	0.0489 (13)
H7A	−0.0822	0.1200	0.4819	0.073*
H7B	−0.1117	0.1981	0.4388	0.073*
H7C	−0.0164	0.2451	0.4741	0.073*
C8	−0.1145 (4)	−0.0332 (5)	0.38813 (15)	0.0479 (13)
H8A	−0.1122	−0.0757	0.3609	0.072*
H8B	−0.1577	0.0437	0.3834	0.072*
H8C	−0.1470	−0.0895	0.4073	0.072*
C9	0.1016 (4)	−0.1771 (4)	0.37448 (15)	0.0471 (13)
H9A	0.1719	−0.1755	0.3644	0.071*
H9B	0.0444	−0.1721	0.3501	0.071*
H9C	0.0941	−0.2556	0.3901	0.071*
C10	0.2918 (4)	−0.0755 (4)	0.43991 (16)	0.0464 (12)
H10A	0.2859	−0.1630	0.4491	0.070*
H10B	0.3367	−0.0279	0.4622	0.070*
H10C	0.3247	−0.0734	0.4137	0.070*
P1	0.01571 (8)	0.27318 (10)	0.34249 (3)	0.0243 (2)
C11A	−0.0839 (3)	0.3702 (4)	0.36536 (11)	0.0253 (8)
C12A	−0.1899 (3)	0.3329 (4)	0.36497 (13)	0.0322 (10)
F12A	−0.22560 (18)	0.2244 (2)	0.34630 (8)	0.0442 (7)
C13A	−0.2644 (3)	0.4012 (4)	0.38383 (14)	0.0368 (11)
F13A	−0.3655 (2)	0.3605 (3)	0.38198 (9)	0.0552 (8)
C14A	−0.2331 (4)	0.5123 (4)	0.40430 (14)	0.0396 (11)
F14A	−0.3026 (2)	0.5787 (3)	0.42356 (9)	0.0577 (8)
C15A	−0.1292 (4)	0.5530 (4)	0.40570 (13)	0.0361 (11)
F15A	−0.0969 (2)	0.6597 (2)	0.42586 (9)	0.0553 (8)
C16A	−0.0572 (3)	0.4830 (4)	0.38573 (13)	0.0305 (10)
F16A	0.04305 (19)	0.5298 (2)	0.38709 (8)	0.0406 (6)
C11B	−0.0692 (3)	0.2292 (4)	0.29221 (12)	0.0284 (9)
C12B	−0.0825 (3)	0.1088 (4)	0.27615 (13)	0.0314 (10)
F12B	−0.03597 (19)	0.0094 (2)	0.29806 (8)	0.0391 (6)
C13B	−0.1424 (4)	0.0806 (5)	0.23738 (14)	0.0396 (11)
F13B	−0.1493 (2)	−0.0382 (3)	0.22318 (8)	0.0530 (7)
C14B	−0.1957 (4)	0.1761 (5)	0.21398 (14)	0.0428 (12)
F14B	−0.2558 (2)	0.1507 (3)	0.17677 (8)	0.0633 (9)
C15B	−0.1852 (3)	0.2980 (5)	0.22826 (14)	0.0396 (11)
F15B	−0.2360 (2)	0.3917 (3)	0.20523 (8)	0.0529 (7)
C16B	−0.1228 (3)	0.3231 (4)	0.26627 (13)	0.0304 (10)
F16B	−0.11495 (18)	0.4451 (2)	0.27840 (7)	0.0378 (6)
C1A	0.1091 (3)	0.3770 (4)	0.31799 (12)	0.0283 (9)
H1A1	0.1290	0.3347	0.2924	0.034*
H1A2	0.0708	0.4558	0.3086	0.034*
C2A	0.2128 (3)	0.4109 (4)	0.34770 (12)	0.0291 (9)
H2A1	0.2033	0.4932	0.3613	0.035*
H2A2	0.2731	0.4190	0.3308	0.035*
P2	0.24670 (8)	0.28992 (10)	0.38917 (3)	0.0261 (2)
C21A	0.3767 (3)	0.2212 (4)	0.38038 (14)	0.0314 (10)
C22A	0.4452 (3)	0.1681 (4)	0.41375 (15)	0.0371 (11)
F22A	0.4254 (2)	0.1869 (2)	0.45387 (8)	0.0457 (7)
C23A	0.5333 (4)	0.0951 (4)	0.40833 (19)	0.0478 (13)
F23A	0.5957 (2)	0.0465 (3)	0.44162 (11)	0.0735 (10)
C24A	0.5545 (4)	0.0730 (5)	0.3679 (2)	0.0575 (16)
F24A	0.6387 (2)	−0.0004 (3)	0.36203 (13)	0.0825 (11)
C25A	0.4908 (4)	0.1249 (5)	0.33344 (18)	0.0527 (14)
F25A	0.5121 (2)	0.1039 (3)	0.29398 (11)	0.0774 (10)
C26A	0.4045 (4)	0.1966 (4)	0.34006 (15)	0.0394 (11)
F26A	0.3439 (2)	0.2439 (3)	0.30516 (8)	0.0481 (7)
C21B	0.2839 (3)	0.4011 (4)	0.43330 (13)	0.0311 (10)
C22B	0.2068 (4)	0.4407 (4)	0.45785 (13)	0.0349 (10)
F22B	0.1089 (2)	0.3850 (2)	0.45389 (8)	0.0421 (6)
C23B	0.2221 (4)	0.5382 (4)	0.48622 (14)	0.0423 (12)
F23B	0.1433 (3)	0.5716 (3)	0.50852 (9)	0.0625 (8)
C24B	0.3180 (5)	0.6007 (5)	0.49196 (15)	0.0523 (14)
F24B	0.3349 (3)	0.6951 (3)	0.52025 (9)	0.0691 (9)
C25B	0.3983 (4)	0.5671 (4)	0.46856 (15)	0.0453 (13)
F25B	0.4913 (2)	0.6298 (3)	0.47281 (9)	0.0606 (8)
C26B	0.3801 (4)	0.4689 (4)	0.43942 (14)	0.0356 (11)
F26B	0.45955 (19)	0.4423 (2)	0.41727 (9)	0.0454 (7)
N1S	0.1761 (3)	0.0731 (3)	0.33285 (10)	0.0268 (8)
C2S	0.2011 (3)	0.0292 (4)	0.30337 (14)	0.0310 (10)
C3S	0.2301 (4)	−0.0259 (5)	0.26464 (14)	0.0494 (13)
H3S1	0.1680	−0.0223	0.2422	0.074*
H3S2	0.2515	−0.1139	0.2699	0.074*
H3S3	0.2902	0.0213	0.2557	0.074*
P3	0.40845 (10)	0.71325 (12)	0.33113 (4)	0.0385 (3)
F31	0.5311 (2)	0.7346 (3)	0.34824 (10)	0.0687 (9)
F32	0.3840 (2)	0.6759 (3)	0.37704 (9)	0.0632 (9)
F33	0.4288 (2)	0.7504 (3)	0.28423 (9)	0.0632 (8)
F34	0.2840 (2)	0.6917 (3)	0.31325 (9)	0.0564 (8)
F35	0.4325 (2)	0.5692 (3)	0.32137 (9)	0.0564 (8)
F36	0.3821 (2)	0.8565 (2)	0.34084 (9)	0.0568 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.02723 (18)	0.02367 (17)	0.02360 (17)	0.00175 (15)	0.00433 (12)	0.00038 (15)
C1	0.044 (3)	0.029 (2)	0.031 (2)	0.003 (2)	0.010 (2)	0.0092 (19)
C2	0.039 (3)	0.035 (3)	0.031 (2)	0.004 (2)	0.015 (2)	0.0086 (19)
C3	0.040 (3)	0.027 (2)	0.035 (2)	−0.004 (2)	0.009 (2)	0.0088 (19)
C4	0.041 (3)	0.025 (2)	0.033 (2)	−0.003 (2)	0.010 (2)	0.0072 (19)
C5	0.040 (3)	0.023 (2)	0.031 (2)	0.0073 (19)	0.0073 (19)	0.0087 (18)
C6	0.057 (3)	0.040 (3)	0.030 (2)	0.006 (2)	0.006 (2)	0.005 (2)
C7	0.057 (3)	0.047 (3)	0.049 (3)	0.010 (2)	0.027 (3)	0.015 (2)
C8	0.041 (3)	0.052 (3)	0.052 (3)	−0.011 (2)	0.010 (2)	0.010 (3)
C9	0.066 (3)	0.025 (2)	0.052 (3)	−0.007 (2)	0.013 (3)	−0.003 (2)
C10	0.048 (3)	0.041 (3)	0.048 (3)	0.010 (2)	0.002 (2)	0.012 (2)
P1	0.0239 (5)	0.0253 (6)	0.0234 (5)	0.0000 (4)	0.0026 (4)	−0.0004 (4)
C11A	0.031 (2)	0.025 (2)	0.0198 (19)	−0.0004 (19)	0.0047 (16)	0.0007 (17)
C12A	0.035 (2)	0.032 (3)	0.029 (2)	−0.0006 (19)	0.0029 (19)	0.0005 (19)
F12A	0.0308 (14)	0.0447 (16)	0.0590 (18)	−0.0066 (12)	0.0125 (12)	−0.0120 (13)
C13A	0.032 (3)	0.047 (3)	0.034 (3)	0.004 (2)	0.011 (2)	0.005 (2)
F13A	0.0368 (16)	0.0644 (19)	0.069 (2)	0.0035 (14)	0.0224 (14)	−0.0053 (16)
C14A	0.051 (3)	0.040 (3)	0.031 (2)	0.021 (2)	0.017 (2)	0.005 (2)
F14A	0.0669 (19)	0.0585 (19)	0.0531 (18)	0.0256 (16)	0.0272 (15)	−0.0024 (15)
C15A	0.054 (3)	0.027 (2)	0.028 (2)	0.007 (2)	0.006 (2)	−0.0041 (19)
F15A	0.076 (2)	0.0374 (17)	0.0552 (18)	0.0038 (14)	0.0175 (15)	−0.0154 (13)
C16A	0.034 (2)	0.027 (2)	0.030 (2)	0.0031 (19)	0.0033 (19)	0.0042 (18)
F16A	0.0422 (15)	0.0306 (14)	0.0495 (16)	−0.0077 (12)	0.0074 (12)	−0.0119 (12)
C11B	0.025 (2)	0.035 (2)	0.025 (2)	−0.0009 (19)	0.0061 (17)	0.0017 (19)
C12B	0.027 (2)	0.035 (3)	0.033 (2)	−0.0014 (19)	0.0066 (18)	−0.0035 (19)
F12B	0.0419 (15)	0.0299 (14)	0.0446 (15)	−0.0034 (11)	0.0023 (12)	−0.0075 (12)
C13B	0.037 (3)	0.045 (3)	0.037 (3)	−0.009 (2)	0.007 (2)	−0.018 (2)
F13B	0.0536 (17)	0.0562 (18)	0.0483 (17)	−0.0147 (14)	0.0044 (14)	−0.0241 (14)
C14B	0.036 (3)	0.063 (3)	0.027 (2)	−0.006 (2)	−0.005 (2)	−0.011 (2)
F14B	0.0589 (18)	0.091 (2)	0.0336 (15)	−0.0083 (17)	−0.0157 (13)	−0.0137 (16)
C15B	0.030 (2)	0.056 (3)	0.031 (2)	0.000 (2)	0.002 (2)	0.008 (2)
F15B	0.0505 (17)	0.071 (2)	0.0330 (15)	0.0090 (15)	−0.0099 (12)	0.0093 (14)
C16B	0.027 (2)	0.036 (3)	0.027 (2)	−0.0011 (18)	0.0010 (18)	−0.0025 (19)
F16B	0.0409 (15)	0.0375 (15)	0.0333 (14)	0.0045 (12)	−0.0008 (11)	0.0050 (11)
C1A	0.026 (2)	0.033 (2)	0.027 (2)	−0.0014 (19)	0.0031 (17)	−0.0009 (19)
C2A	0.025 (2)	0.032 (2)	0.030 (2)	−0.0053 (18)	0.0023 (17)	0.0031 (18)
P2	0.0255 (6)	0.0279 (6)	0.0242 (5)	0.0011 (5)	0.0006 (4)	−0.0017 (5)
C21A	0.028 (2)	0.028 (2)	0.037 (2)	−0.0032 (18)	0.0010 (19)	−0.0030 (19)
C22A	0.033 (2)	0.032 (3)	0.043 (3)	−0.0020 (19)	−0.006 (2)	−0.012 (2)
F22A	0.0494 (16)	0.0422 (15)	0.0407 (16)	0.0090 (13)	−0.0100 (13)	−0.0002 (13)
C23A	0.029 (3)	0.032 (3)	0.077 (4)	0.003 (2)	−0.009 (3)	−0.009 (3)
F23A	0.0492 (18)	0.0526 (19)	0.108 (3)	0.0183 (15)	−0.0249 (18)	−0.0076 (18)
C24A	0.025 (3)	0.050 (3)	0.098 (5)	−0.004 (2)	0.013 (3)	−0.028 (3)
F24A	0.0333 (17)	0.066 (2)	0.151 (3)	0.0068 (15)	0.0211 (19)	−0.034 (2)
C25A	0.034 (3)	0.061 (4)	0.068 (4)	−0.008 (3)	0.024 (3)	−0.027 (3)
F25A	0.063 (2)	0.092 (3)	0.087 (2)	−0.0090 (18)	0.0463 (18)	−0.037 (2)
C26A	0.033 (3)	0.046 (3)	0.040 (3)	−0.006 (2)	0.008 (2)	−0.010 (2)
F26A	0.0518 (17)	0.0596 (18)	0.0351 (15)	−0.0093 (14)	0.0142 (13)	−0.0070 (13)
C21B	0.038 (3)	0.024 (2)	0.030 (2)	0.0091 (18)	−0.0005 (19)	0.0008 (18)
C22B	0.048 (3)	0.031 (3)	0.025 (2)	0.003 (2)	0.001 (2)	0.0052 (19)
F22B	0.0463 (16)	0.0408 (16)	0.0423 (15)	0.0066 (13)	0.0167 (12)	−0.0004 (12)
C23B	0.067 (3)	0.035 (3)	0.025 (2)	0.008 (3)	0.007 (2)	−0.002 (2)
F23B	0.098 (2)	0.0507 (18)	0.0421 (17)	0.0231 (17)	0.0206 (16)	−0.0075 (14)
C24B	0.085 (4)	0.035 (3)	0.031 (3)	0.009 (3)	−0.013 (3)	−0.007 (2)
F24B	0.120 (3)	0.0408 (17)	0.0405 (17)	0.0050 (18)	−0.0106 (17)	−0.0196 (14)
C25B	0.052 (3)	0.036 (3)	0.040 (3)	−0.001 (2)	−0.020 (2)	−0.003 (2)
F25B	0.0635 (19)	0.0414 (16)	0.066 (2)	−0.0095 (15)	−0.0272 (15)	−0.0095 (15)
C26B	0.038 (3)	0.033 (3)	0.032 (2)	0.003 (2)	−0.009 (2)	−0.002 (2)
F26B	0.0336 (15)	0.0391 (16)	0.0623 (18)	−0.0032 (12)	0.0020 (13)	−0.0102 (13)
N1S	0.0259 (18)	0.0254 (19)	0.0288 (19)	0.0000 (15)	0.0032 (15)	−0.0003 (15)
C2S	0.032 (2)	0.030 (2)	0.030 (2)	0.0037 (19)	0.0029 (19)	0.0013 (19)
C3S	0.067 (3)	0.055 (3)	0.029 (3)	0.018 (3)	0.012 (2)	−0.004 (2)
P3	0.0419 (7)	0.0380 (7)	0.0364 (7)	−0.0014 (6)	0.0082 (5)	−0.0006 (6)
F31	0.0456 (18)	0.079 (2)	0.076 (2)	−0.0089 (16)	−0.0086 (16)	−0.0006 (18)
F32	0.090 (2)	0.0595 (19)	0.0432 (17)	0.0183 (17)	0.0217 (16)	0.0120 (14)
F33	0.064 (2)	0.084 (2)	0.0467 (18)	0.0111 (17)	0.0239 (15)	0.0129 (16)
F34	0.0431 (17)	0.0541 (18)	0.072 (2)	0.0021 (14)	0.0070 (14)	−0.0095 (15)
F35	0.0586 (19)	0.0450 (17)	0.065 (2)	0.0121 (14)	0.0082 (15)	−0.0106 (15)
F36	0.078 (2)	0.0362 (16)	0.0549 (18)	−0.0010 (15)	0.0062 (15)	−0.0038 (14)

Geometric parameters (Å, º) top

Ru1—N1S	2.048 (3)	C12B—C13B	1.382 (6)
Ru1—C5	2.224 (4)	C13B—F13B	1.339 (5)
Ru1—C2	2.235 (4)	C13B—C14B	1.374 (6)
Ru1—C1	2.238 (4)	C14B—F14B	1.337 (5)
Ru1—C3	2.244 (4)	C14B—C15B	1.371 (6)
Ru1—C4	2.247 (4)	C15B—F15B	1.342 (5)
Ru1—P2	2.2936 (11)	C15B—C16B	1.370 (6)
Ru1—P1	2.3019 (11)	C16B—F16B	1.351 (5)
C1—C2	1.432 (6)	C1A—C2A	1.538 (5)
C1—C5	1.434 (6)	C1A—H1A1	0.9900
C1—C6	1.503 (6)	C1A—H1A2	0.9900
C2—C3	1.433 (6)	C2A—P2	1.846 (4)
C2—C7	1.496 (6)	C2A—H2A1	0.9900
C3—C4	1.410 (6)	C2A—H2A2	0.9900
C3—C8	1.515 (6)	P2—C21B	1.841 (4)
C4—C5	1.435 (6)	P2—C21A	1.842 (4)
C4—C9	1.486 (6)	C21A—C22A	1.387 (6)
C5—C10	1.510 (6)	C21A—C26A	1.398 (6)
C6—H6A	0.9800	C22A—F22A	1.347 (5)
C6—H6B	0.9800	C22A—C23A	1.380 (6)
C6—H6C	0.9800	C23A—F23A	1.328 (5)
C7—H7A	0.9800	C23A—C24A	1.367 (7)
C7—H7B	0.9800	C24A—F24A	1.347 (5)
C7—H7C	0.9800	C24A—C25A	1.377 (8)
C8—H8A	0.9800	C25A—F25A	1.336 (6)
C8—H8B	0.9800	C25A—C26A	1.363 (6)
C8—H8C	0.9800	C26A—F26A	1.349 (5)
C9—H9A	0.9800	C21B—C22B	1.389 (6)
C9—H9B	0.9800	C21B—C26B	1.395 (6)
C9—H9C	0.9800	C22B—F22B	1.352 (5)
C10—H10A	0.9800	C22B—C23B	1.368 (6)
C10—H10B	0.9800	C23B—F23B	1.341 (5)
C10—H10C	0.9800	C23B—C24B	1.363 (7)
P1—C11A	1.844 (4)	C24B—F24B	1.342 (5)
P1—C11B	1.851 (4)	C24B—C25B	1.379 (7)
P1—C1A	1.857 (4)	C25B—F25B	1.333 (5)
C11A—C16A	1.380 (5)	C25B—C26B	1.391 (6)
C11A—C12A	1.385 (5)	C26B—F26B	1.328 (5)
C12A—F12A	1.343 (4)	N1S—C2S	1.129 (5)
C12A—C13A	1.384 (6)	C2S—C3S	1.453 (6)
C13A—F13A	1.333 (5)	C3S—H3S1	0.9800
C13A—C14A	1.377 (6)	C3S—H3S2	0.9800
C14A—F14A	1.334 (5)	C3S—H3S3	0.9800
C14A—C15A	1.367 (6)	P3—F31	1.574 (3)
C15A—F15A	1.335 (5)	P3—F32	1.582 (3)
C15A—C16A	1.389 (6)	P3—F36	1.595 (3)
C16A—F16A	1.347 (5)	P3—F33	1.596 (3)
C11B—C12B	1.378 (6)	P3—F35	1.598 (3)
C11B—C16B	1.403 (5)	P3—F34	1.600 (3)
C12B—F12B	1.351 (5)

N1S—Ru1—C5	100.19 (14)	F14A—C14A—C13A	120.5 (4)
N1S—Ru1—C2	148.71 (15)	C15A—C14A—C13A	119.6 (4)
C5—Ru1—C2	62.76 (15)	F15A—C15A—C14A	120.5 (4)
N1S—Ru1—C1	137.05 (14)	F15A—C15A—C16A	120.0 (4)
C5—Ru1—C1	37.50 (14)	C14A—C15A—C16A	119.5 (4)
C2—Ru1—C1	37.33 (15)	F16A—C16A—C11A	119.9 (4)
N1S—Ru1—C3	112.23 (14)	F16A—C16A—C15A	116.8 (4)
C5—Ru1—C3	62.26 (15)	C11A—C16A—C15A	123.3 (4)
C2—Ru1—C3	37.31 (15)	C12B—C11B—C16B	114.7 (4)
C1—Ru1—C3	62.03 (16)	C12B—C11B—P1	125.4 (3)
N1S—Ru1—C4	88.30 (14)	C16B—C11B—P1	119.8 (3)
C5—Ru1—C4	37.45 (15)	F12B—C12B—C11B	120.9 (4)
C2—Ru1—C4	61.98 (16)	F12B—C12B—C13B	115.5 (4)
C1—Ru1—C4	62.01 (16)	C11B—C12B—C13B	123.6 (4)
C3—Ru1—C4	36.61 (15)	F13B—C13B—C14B	120.6 (4)
N1S—Ru1—P2	86.22 (9)	F13B—C13B—C12B	120.4 (4)
C5—Ru1—P2	108.57 (11)	C14B—C13B—C12B	119.0 (4)
C2—Ru1—P2	123.19 (12)	F14B—C14B—C15B	119.9 (4)
C1—Ru1—P2	99.58 (12)	F14B—C14B—C13B	120.0 (4)
C3—Ru1—P2	160.09 (11)	C15B—C14B—C13B	120.0 (4)
C4—Ru1—P2	143.49 (11)	F15B—C15B—C16B	120.3 (4)
N1S—Ru1—P1	85.92 (9)	F15B—C15B—C14B	120.2 (4)
C5—Ru1—P1	166.43 (11)	C16B—C15B—C14B	119.5 (4)
C2—Ru1—P1	106.06 (11)	F16B—C16B—C15B	116.6 (4)
C1—Ru1—P1	136.89 (11)	F16B—C16B—C11B	120.3 (3)
C3—Ru1—P1	104.24 (11)	C15B—C16B—C11B	123.1 (4)
C4—Ru1—P1	131.80 (11)	C2A—C1A—P1	114.2 (3)
P2—Ru1—P1	83.77 (4)	C2A—C1A—H1A1	108.7
C2—C1—C5	108.2 (4)	P1—C1A—H1A1	108.7
C2—C1—C6	126.8 (4)	C2A—C1A—H1A2	108.7
C5—C1—C6	123.9 (4)	P1—C1A—H1A2	108.7
C2—C1—Ru1	71.3 (2)	H1A1—C1A—H1A2	107.6
C5—C1—Ru1	70.7 (2)	C1A—C2A—P2	111.4 (3)
C6—C1—Ru1	132.8 (3)	C1A—C2A—H2A1	109.3
C1—C2—C3	107.4 (4)	P2—C2A—H2A1	109.3
C1—C2—C7	125.7 (4)	C1A—C2A—H2A2	109.3
C3—C2—C7	125.7 (4)	P2—C2A—H2A2	109.3
C1—C2—Ru1	71.4 (2)	H2A1—C2A—H2A2	108.0
C3—C2—Ru1	71.7 (2)	C21B—P2—C21A	103.55 (19)
C7—C2—Ru1	132.1 (3)	C21B—P2—C2A	96.07 (18)
C4—C3—C2	108.5 (4)	C21A—P2—C2A	106.68 (19)
C4—C3—C8	125.7 (4)	C21B—P2—Ru1	126.11 (15)
C2—C3—C8	125.0 (4)	C21A—P2—Ru1	109.75 (13)
C4—C3—Ru1	71.8 (2)	C2A—P2—Ru1	112.68 (13)
C2—C3—Ru1	71.0 (2)	C22A—C21A—C26A	114.6 (4)
C8—C3—Ru1	130.9 (3)	C22A—C21A—P2	120.8 (3)
C3—C4—C5	108.5 (4)	C26A—C21A—P2	123.5 (3)
C3—C4—C9	127.0 (4)	F22A—C22A—C23A	117.3 (4)
C5—C4—C9	124.5 (4)	F22A—C22A—C21A	119.1 (4)
C3—C4—Ru1	71.6 (2)	C23A—C22A—C21A	123.6 (5)
C5—C4—Ru1	70.4 (2)	F23A—C23A—C24A	120.7 (5)
C9—C4—Ru1	125.2 (3)	F23A—C23A—C22A	120.7 (5)
C1—C5—C4	107.2 (4)	C24A—C23A—C22A	118.5 (5)
C1—C5—C10	127.8 (4)	F24A—C24A—C23A	119.3 (5)
C4—C5—C10	124.2 (4)	F24A—C24A—C25A	120.0 (5)
C1—C5—Ru1	71.8 (2)	C23A—C24A—C25A	120.7 (5)
C4—C5—Ru1	72.1 (2)	F25A—C25A—C26A	120.4 (5)
C10—C5—Ru1	129.5 (3)	F25A—C25A—C24A	120.6 (5)
C1—C6—H6A	109.5	C26A—C25A—C24A	119.0 (5)
C1—C6—H6B	109.5	F26A—C26A—C25A	116.6 (4)
H6A—C6—H6B	109.5	F26A—C26A—C21A	120.0 (4)
C1—C6—H6C	109.5	C25A—C26A—C21A	123.4 (5)
H6A—C6—H6C	109.5	C22B—C21B—C26B	114.9 (4)
H6B—C6—H6C	109.5	C22B—C21B—P2	120.0 (3)
C2—C7—H7A	109.5	C26B—C21B—P2	124.0 (3)
C2—C7—H7B	109.5	F22B—C22B—C23B	115.7 (4)
H7A—C7—H7B	109.5	F22B—C22B—C21B	120.6 (4)
C2—C7—H7C	109.5	C23B—C22B—C21B	123.7 (5)
H7A—C7—H7C	109.5	F23B—C23B—C24B	120.1 (4)
H7B—C7—H7C	109.5	F23B—C23B—C22B	120.1 (5)
C3—C8—H8A	109.5	C24B—C23B—C22B	119.8 (5)
C3—C8—H8B	109.5	F24B—C24B—C23B	120.4 (5)
H8A—C8—H8B	109.5	F24B—C24B—C25B	119.7 (5)
C3—C8—H8C	109.5	C23B—C24B—C25B	119.9 (4)
H8A—C8—H8C	109.5	F25B—C25B—C24B	120.7 (4)
H8B—C8—H8C	109.5	F25B—C25B—C26B	120.0 (5)
C4—C9—H9A	109.5	C24B—C25B—C26B	119.2 (5)
C4—C9—H9B	109.5	F26B—C26B—C25B	116.5 (4)
H9A—C9—H9B	109.5	F26B—C26B—C21B	121.0 (4)
C4—C9—H9C	109.5	C25B—C26B—C21B	122.5 (5)
H9A—C9—H9C	109.5	C2S—N1S—Ru1	173.1 (3)
H9B—C9—H9C	109.5	N1S—C2S—C3S	178.2 (5)
C5—C10—H10A	109.5	C2S—C3S—H3S1	109.5
C5—C10—H10B	109.5	C2S—C3S—H3S2	109.5
H10A—C10—H10B	109.5	H3S1—C3S—H3S2	109.5
C5—C10—H10C	109.5	C2S—C3S—H3S3	109.5
H10A—C10—H10C	109.5	H3S1—C3S—H3S3	109.5
H10B—C10—H10C	109.5	H3S2—C3S—H3S3	109.5
C11A—P1—C11B	98.14 (17)	F31—P3—F32	91.37 (18)
C11A—P1—C1A	109.58 (18)	F31—P3—F36	90.86 (17)
C11B—P1—C1A	96.20 (17)	F32—P3—F36	89.35 (16)
C11A—P1—Ru1	118.14 (12)	F31—P3—F33	90.61 (17)
C11B—P1—Ru1	124.75 (14)	F32—P3—F33	178.02 (18)
C1A—P1—Ru1	107.53 (13)	F36—P3—F33	90.52 (16)
C16A—C11A—C12A	114.9 (4)	F31—P3—F35	90.16 (17)
C16A—C11A—P1	122.4 (3)	F32—P3—F35	90.29 (16)
C12A—C11A—P1	122.6 (3)	F36—P3—F35	178.93 (17)
F12A—C12A—C13A	115.9 (4)	F33—P3—F35	89.80 (17)
F12A—C12A—C11A	120.6 (4)	F31—P3—F34	179.43 (18)
C13A—C12A—C11A	123.5 (4)	F32—P3—F34	89.20 (17)
F13A—C13A—C14A	120.3 (4)	F36—P3—F34	89.24 (16)
F13A—C13A—C12A	120.5 (4)	F33—P3—F34	88.83 (16)
C14A—C13A—C12A	119.2 (4)	F35—P3—F34	89.75 (15)
F14A—C14A—C15A	119.9 (4)

Acknowledgements

We thank the EPSRC for support.

References

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)