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Acta Cryst. (2007). E63, m1627    [ doi:10.1107/S1600536807021861 ]

Chlorido(6,7-dimethyl-2,3-dipyridin-2-ylquinoxaline-[kappa]2N,N')([eta]6-1,2,4,5-tetramethylbenzene)ruthenium(II) hexafluorophosphate acetonitrile solvate

B. Therrien and G. Süss-Fink

Abstract top

In the title salt, [RuCl(C10H14)(C20H16N4)]PF6·CH3CN, the coordination of one pyridyl ring and of one N atom of the quinoxaline unit to ruthenium imposes considerable distortion on the 6,7-dimethyl-2,3-dipyridin-2-ylquinoxaline ligand. Indeed, the pyridyl ring and the plane of the quinoxaline unit become almost coplanar.

Comment top

The title complex (I) shows a typical piano-stool geometry with the metal centre coordinated by the arene ligand, a terminal chloride and the chelating 6,7-dimethyl-2,3-di(pyridin-2-yl)quinoxaline (dpqMe2) ligand. In the mononuclear complex (I), the metal centre is stereogenic. However, since none of the ligand contains a chiral information, (I) is obtained as a racemic mixture.

The Ru—N bond distances 2.060 (2) and 2.077 (2) Å in (I) are comparable to those in [(η6-p-PriC6H4Me)RuCl(η2-2,3-bis(2-pyridyl)pyrazine)][BF4] (Singh et al., 2002) and [(η6-p-PriC6H4Me)RuCl(η2-2,3-bis(α-pyridyl)quinoxaline)][PF6] (Lalrempuia & Kollipara, 2003). Accordingly, there is no significant difference in the Ru—Cl bond length in (I) [2.3732 (9) Å] and reported values (Lalrempuia & Kollipara, 2003)(Scott et al., 1999)(Canivet et al., 2005). The N(1)—Ru(1)—N(2) bond angle in complex (I) [76.04 (9)°] is similar to those of complexes [(η6-p-PriC6H4Me)RuCl(η2-2,3-bis(2-pyridyl)pyrazine)]+ [N(1)—Ru(1)—N(2) = 76.5 (2)°] (Singh et al., 2002) and [(η6-p-PriC6H4Me)RuCl(η2-2,3-bis(α-pyridyl)quinoxaline)]+ [N(1)—Ru(1)—N(2) = 76.2 (2)°] (Lalrempuia & Kollipara, 2003). An ORTEP drawing with the atom labelling scheme for (I) is shown in Figure 1.

Upon formation of the mononuclear complex (I), the bond length between the connecting carbon atoms [C(5)—C(6) = 1.472 (4) Å] of the coordinated pyridyl and quinoxaline moieties of the dpqMe2 ligand is slightly reduced as compared to the corresponding connecting C—C atoms [C(7)—C(8) = 1.496 (4) Å] of the non-coordinated pyridyl quinoxaline moities. Similarly, the C—C distances [1.493 Å] in the free dpqMe2 are longer (Wozniak et al., 1993). These bond length changes are in agreement with a back-donation from the metallic fragments to the dpqMe2 system, thus increasing the inter-ring bond order (Baumann et al., 1998) (Berg et al., 2002).

The major distortion imposed on the dpqMe2 structure upon coordination is encountered by the pyridyl groups. In the free ligand the two equivalent pyridyl groups are twisted by 39.6° relative to the plane of the quinoxaline unit (Wozniak et al., 1993). However, in (I) the twist of the coordinated pyridyl unit is 22.7 (1)°, while the non-coordinated pyridyl group is twisted by 54.2 (1)° relative to the plane of the quinoxaline unit.

Related literature top

The non-coordinated dpqMe2 ligand crystallizes in the centrosymmetric space group P21/a (Wozniak et al., 1993). Other arene–ruthenium and osmium complexes with chelating quinoxaline pyridyl derivatives have been synthesized and characterized by X-ray structure analysis (Baumann et al., 1998; Scott et al., 1999; Lalrempuia & Kollipara, 2003; Therrien et al., 2007).

For related literature, see: Berg et al. (2002); Canivet et al. (2005); Singh et al. (2002).

Experimental top

The dinuclear complex [(η6-1,2,4,5-C6H2Me4)Ru(µ-Cl)Cl]2 (70 mg, 0.11 mmol) is dissolved in methanol (50 ml). The resulting solution is added dropwise to a two-necked flask equipped with a reflux condenser and containing a methanol solution (50 ml) of dpqMe2 (71 mg, 0.23 mmol) and KPF6 (42 mg, 0.11 mmol). The mixture is heated to 50°C and stirred for 24 h. After cooling to room temperature, the volume is reduced and the product is precipitated by addition of diethylether. The orange solid is filtered, washed with n-pentane and dried under vacuo to give [(η6-1,2,4,5-C6H2Me4)RuCl(dpqMe2)][PF6] (130 mg, 0.12 mmol, yield 78.1%).

Crystals of (I) were obtained by the slow diffusion of diethylether into an acetonitrile solution of (I).

1H NMR (400 MHz, CD3CN): δ (p.p.m.) = 9.13 (d, 1H), 8.62 (d, 1H), 8.37 (s, 1H), 8.20 (m, 2H), 8.07 (s, 1H), 7.80 (dd, 1H), 7.64 (m, 2H), 7.10 (d, 1H), 5.63 (s, 2H), 2.69 (s, 3H), 2.65 (s, 3H), 2.19 (s, 6H), 2.12 (s, 6H,); IR (KBr, cm-1): 842 s υ(P—F), 558 m; ESI-MS (m/z): 583.1 [M+]; Anal. Calc. for C30H30N4ClF6PRu: C, 49.49; H, 4.15; N, 7.70. Found: C, 49.33; H, 4.26; N, 7.49.

Refinement top

The H atoms were included in calculated positions and refined using a riding model (including free rotation about the acetonitrile C—C bond), with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Computing details top

Data collection: EXPOSE (Stoe, 2000); cell refinement: CELL (Stoe, 2000); data reduction: INTEGRATE (Stoe, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 2001); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) at 50% probability level with hydrogen atoms, acetonitrile molecule and hexafluorophosphate anion being omitted for clarity.
Chlorido(6,7-dimethyl-2,3-dipyridin-2-ylquinoxaline-κ2N,N')(η6– 1,2,4,5-tetramethylbenzene)ruthenium(II) hexafluorophosphate acetonitrile solvate top
Crystal data top
[RuCl(C10H14)(C20H16N4)]PF6·C2H3NF(000) = 1560
Mr = 769.12Dx = 1.539 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 8000 reflections
a = 13.1725 (11) Åθ = 2.1–26.0°
b = 25.6651 (17) ŵ = 0.67 mm−1
c = 10.1222 (9) ÅT = 173 K
β = 104.14 (1)°Block, orange
V = 3318.4 (5) Å30.34 × 0.22 × 0.19 mm
Z = 4
Data collection top
Stoe IPDS
diffractometer		5710 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
graphiteθmax = 26.0°, θmin = 2.4°
Detector resolution: 0.81Å pixels mm-1h = −16→16
phi oscillation scansk = −31→31
13015 measured reflectionsl = −12→12
6142 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.064 w = 1/[σ2(Fo2) + (0.042P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
6142 reflectionsΔρmax = 0.51 e Å−3
422 parametersΔρmin = −0.27 e Å−3
2 restraintsAbsolute structure: Flack (1983), 2912 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.01 (2)
Crystal data top
[RuCl(C10H14)(C20H16N4)]PF6·C2H3NV = 3318.4 (5) Å3
Mr = 769.12Z = 4
Monoclinic, CcMo Kα radiation
a = 13.1725 (11) ŵ = 0.67 mm−1
b = 25.6651 (17) ÅT = 173 K
c = 10.1222 (9) Å0.34 × 0.22 × 0.19 mm
β = 104.14 (1)°
Data collection top
Stoe IPDS
diffractometer		5710 reflections with I > 2σ(I)
13015 measured reflectionsRint = 0.034
6142 independent reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.064Δρmax = 0.51 e Å−3
S = 1.01Δρmin = −0.27 e Å−3
6142 reflectionsAbsolute structure: Flack (1983), 2912 Friedel pairs
422 parametersFlack parameter: −0.01 (2)
2 restraints
Special details top

Experimental. A crystal was mounted at 173 K on a Stoe Image Plate Diffraction System (Stoe & Cie, 2000) using Mo Kα graphite monochromated radiation. Image plate distance 70 mm, φ oscillation scans 0 - 200°, step Δφ = 1.0°, 3 minutes per frame.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6737 (3)0.39051 (13)0.2351 (3)0.0307 (7)
H10.70450.37670.16940.037*
C20.6820 (3)0.44337 (14)0.2618 (4)0.0397 (8)
H20.71640.46500.21310.048*
C30.6390 (3)0.46340 (14)0.3613 (4)0.0421 (9)
H30.64390.49890.38060.050*
C40.5882 (3)0.43078 (12)0.4326 (3)0.0317 (7)
H40.56010.44390.50170.038*
C50.5796 (2)0.37805 (11)0.3999 (3)0.0206 (6)
C60.5389 (2)0.33765 (11)0.4764 (3)0.0177 (6)
C70.4808 (2)0.34576 (11)0.5771 (3)0.0198 (6)
C80.4218 (3)0.39516 (13)0.5831 (4)0.0286 (7)
C90.4299 (3)0.42035 (18)0.7062 (4)0.0475 (10)
H90.47660.40910.78540.057*
C100.3656 (4)0.4631 (2)0.7064 (5)0.0673 (14)
H100.36930.48150.78660.081*
C110.2965 (4)0.47820 (17)0.5880 (5)0.0583 (12)
H110.25240.50660.58630.070*
C120.2943 (3)0.45008 (14)0.4719 (4)0.0416 (9)
H120.24730.46020.39160.050*
C130.5065 (2)0.26073 (12)0.6437 (3)0.0197 (6)
C140.5539 (2)0.24969 (11)0.5364 (3)0.0181 (6)
C150.5899 (2)0.19883 (12)0.5216 (3)0.0206 (6)
H150.62300.19180.45230.025*
C160.5769 (2)0.15968 (12)0.6077 (3)0.0231 (6)
C170.5245 (2)0.17017 (12)0.7126 (3)0.0246 (6)
C180.4924 (2)0.22013 (12)0.7308 (3)0.0223 (6)
H180.46080.22710.80160.027*
C190.6161 (3)0.10587 (14)0.5893 (4)0.0386 (8)
H19A0.64780.10570.51340.058*
H19B0.55860.08180.57250.058*
H19C0.66710.09570.67030.058*
C200.5024 (3)0.12652 (14)0.8013 (4)0.0396 (9)
H20A0.46240.13970.86160.059*
H20B0.56730.11240.85370.059*
H20C0.46340.09970.74490.059*
C210.4337 (3)0.25966 (16)0.1676 (4)0.0231 (8)
C220.4661 (2)0.29775 (13)0.0880 (3)0.0238 (6)
C230.5573 (3)0.28838 (11)0.0386 (3)0.0227 (6)
H230.57740.3135−0.01610.027*
C240.6182 (2)0.24295 (13)0.0690 (3)0.0247 (6)
C250.5849 (3)0.20366 (12)0.1513 (3)0.0248 (6)
C260.4947 (2)0.21243 (12)0.1960 (3)0.0245 (7)
H260.47240.18660.24670.029*
C270.3433 (3)0.26601 (16)0.2315 (4)0.0359 (8)
H27A0.34350.30070.26700.054*
H27B0.34950.24130.30430.054*
H27C0.27910.26010.16430.054*
C280.4090 (3)0.34842 (14)0.0542 (4)0.0374 (8)
H28A0.34930.3434−0.02100.056*
H28B0.45490.37380.03010.056*
H28C0.38610.36050.13200.056*
C290.7168 (3)0.23601 (16)0.0209 (4)0.0375 (8)
H29A0.70700.2085−0.04540.056*
H29B0.77360.22720.09690.056*
H29C0.73280.2679−0.01950.056*
C300.6503 (3)0.15529 (13)0.1905 (4)0.0375 (8)
H30A0.62370.13560.25540.056*
H30B0.72160.16500.23030.056*
H30C0.64710.13440.11090.056*
C310.9370 (5)0.5418 (2)0.0826 (5)0.0691 (14)
H31A0.92210.57830.08840.104*
H31B0.87420.52210.07700.104*
H31C0.96240.53550.00280.104*
C321.0143 (4)0.52645 (17)0.2005 (5)0.0536 (11)
Cl10.77649 (7)0.26807 (4)0.37328 (9)0.0297 (2)
F10.6671 (3)0.59853 (15)0.4129 (3)0.0876 (10)
F20.8737 (3)0.61602 (15)0.3128 (5)0.1120 (14)
F30.8192 (3)0.56190 (14)0.4539 (5)0.1267 (18)
F40.7226 (3)0.56792 (12)0.2415 (3)0.0917 (12)
F50.7142 (3)0.65335 (13)0.2704 (4)0.1225 (18)
F60.8135 (3)0.64711 (13)0.4792 (4)0.0918 (11)
N10.62207 (19)0.35849 (10)0.3015 (2)0.0211 (5)
N20.56634 (18)0.28914 (9)0.4497 (2)0.0159 (5)
N30.46743 (18)0.30878 (10)0.6597 (2)0.0216 (5)
N40.3554 (2)0.40938 (11)0.4679 (3)0.0332 (6)
N51.0773 (4)0.51534 (17)0.2953 (5)0.0852 (16)
P10.77074 (8)0.60751 (4)0.35790 (11)0.0365 (2)
Ru10.597916 (16)0.280275 (7)0.259714 (18)0.01590 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0343 (17)0.0305 (18)0.0299 (17)−0.0100 (14)0.0128 (14)0.0035 (13)
C20.053 (2)0.0294 (18)0.0429 (19)−0.0145 (16)0.0231 (18)0.0038 (15)
C30.057 (2)0.0196 (17)0.051 (2)−0.0127 (16)0.0158 (18)−0.0014 (15)
C40.0417 (19)0.0217 (16)0.0345 (17)−0.0069 (14)0.0148 (15)−0.0035 (13)
C50.0210 (14)0.0196 (14)0.0204 (14)−0.0006 (11)0.0039 (11)0.0011 (11)
C60.0157 (12)0.0168 (14)0.0191 (13)−0.0014 (11)0.0012 (10)−0.0016 (11)
C70.0182 (14)0.0208 (14)0.0198 (13)−0.0004 (11)0.0037 (11)−0.0019 (11)
C80.0301 (17)0.0227 (16)0.0362 (19)0.0006 (13)0.0141 (15)−0.0039 (14)
C90.057 (3)0.051 (3)0.036 (2)0.021 (2)0.0134 (18)−0.0081 (18)
C100.096 (4)0.056 (3)0.054 (3)0.026 (3)0.028 (3)−0.015 (2)
C110.061 (3)0.038 (2)0.082 (3)0.028 (2)0.030 (2)0.002 (2)
C120.040 (2)0.0317 (19)0.056 (2)0.0110 (16)0.0162 (18)0.0125 (17)
C130.0154 (13)0.0241 (14)0.0181 (14)−0.0006 (11)0.0012 (11)−0.0002 (11)
C140.0150 (13)0.0203 (15)0.0172 (14)−0.0007 (11)0.0007 (11)0.0038 (11)
C150.0201 (14)0.0247 (15)0.0177 (13)0.0047 (12)0.0057 (11)0.0008 (11)
C160.0238 (14)0.0226 (15)0.0218 (14)0.0039 (12)0.0034 (12)0.0041 (11)
C170.0256 (14)0.0263 (16)0.0204 (14)−0.0024 (12)0.0031 (12)0.0062 (11)
C180.0222 (14)0.0291 (16)0.0171 (12)0.0002 (13)0.0075 (11)0.0039 (12)
C190.049 (2)0.0281 (18)0.044 (2)0.0088 (16)0.0223 (17)0.0085 (15)
C200.053 (2)0.0327 (19)0.0385 (19)0.0021 (17)0.0220 (17)0.0168 (15)
C210.0146 (16)0.0341 (19)0.0184 (16)−0.0089 (14)−0.0002 (12)−0.0070 (15)
C220.0213 (14)0.0308 (16)0.0155 (13)0.0013 (12)−0.0029 (11)0.0000 (12)
C230.0291 (17)0.0237 (16)0.0138 (13)−0.0080 (12)0.0021 (12)0.0022 (11)
C240.0238 (15)0.0326 (17)0.0186 (15)−0.0024 (13)0.0070 (12)−0.0061 (12)
C250.0269 (15)0.0201 (14)0.0244 (14)−0.0019 (12)0.0007 (12)−0.0048 (12)
C260.0255 (15)0.0268 (16)0.0191 (15)−0.0103 (12)0.0012 (12)−0.0013 (11)
C270.0206 (15)0.056 (2)0.0298 (17)−0.0052 (15)0.0042 (14)−0.0038 (15)
C280.0382 (19)0.035 (2)0.0357 (18)0.0122 (15)0.0027 (15)0.0067 (14)
C290.0330 (19)0.049 (2)0.0325 (18)0.0021 (16)0.0126 (15)−0.0084 (16)
C300.046 (2)0.0253 (17)0.0402 (19)0.0090 (15)0.0078 (16)−0.0063 (15)
C310.087 (4)0.069 (3)0.051 (3)−0.015 (3)0.015 (3)−0.003 (2)
C320.059 (3)0.036 (2)0.069 (3)0.0002 (19)0.023 (3)−0.008 (2)
Cl10.0175 (4)0.0464 (5)0.0245 (4)0.0022 (4)0.0035 (3)0.0033 (4)
F10.076 (2)0.106 (3)0.090 (2)−0.0250 (18)0.0380 (17)−0.0415 (19)
F20.108 (3)0.095 (3)0.166 (4)−0.052 (2)0.095 (3)−0.039 (3)
F30.110 (3)0.062 (2)0.184 (4)−0.004 (2)−0.010 (3)0.060 (2)
F40.153 (3)0.069 (2)0.071 (2)−0.060 (2)0.061 (2)−0.0387 (16)
F50.126 (3)0.063 (2)0.130 (3)−0.016 (2)−0.063 (3)0.037 (2)
F60.089 (2)0.076 (2)0.092 (2)−0.0130 (17)−0.0146 (18)−0.0393 (17)
N10.0246 (14)0.0205 (12)0.0181 (12)−0.0054 (9)0.0049 (10)0.0001 (9)
N20.0122 (11)0.0194 (13)0.0159 (11)−0.0009 (9)0.0034 (9)0.0008 (9)
N30.0208 (12)0.0245 (14)0.0199 (12)−0.0016 (10)0.0057 (10)−0.0028 (10)
N40.0310 (15)0.0267 (15)0.0421 (16)0.0016 (12)0.0096 (13)0.0056 (12)
N50.092 (4)0.057 (3)0.097 (4)0.026 (3)0.005 (3)−0.008 (2)
P10.0404 (5)0.0233 (5)0.0451 (6)−0.0048 (4)0.0093 (4)−0.0034 (4)
Ru10.01498 (9)0.01835 (10)0.01457 (9)−0.00139 (12)0.00397 (6)0.00083 (12)
Geometric parameters (Å, °) top
C1—N11.347 (4)C21—C261.444 (5)
C1—C21.382 (5)C21—C271.497 (5)
C1—H10.9300C21—Ru12.200 (3)
C2—C31.370 (6)C22—C231.430 (5)
C2—H20.9300C22—C281.500 (5)
C3—C41.381 (5)C22—Ru12.182 (3)
C3—H30.9300C23—C241.406 (5)
C4—C51.391 (4)C23—Ru12.180 (3)
C4—H40.9300C23—H230.9300
C5—N11.352 (4)C24—C251.443 (5)
C5—C61.472 (4)C24—C291.505 (5)
C6—N21.342 (4)C24—Ru12.229 (3)
C6—C71.431 (4)C25—C261.390 (5)
C7—N31.305 (4)C25—C301.507 (4)
C7—C81.496 (4)C25—Ru12.238 (3)
C8—N41.326 (5)C26—Ru12.206 (3)
C8—C91.384 (5)C26—H260.9300
C9—C101.387 (6)C27—H27A0.9600
C9—H90.9300C27—H27B0.9600
C10—C111.372 (7)C27—H27C0.9600
C10—H100.9300C28—H28A0.9600
C11—C121.373 (6)C28—H28B0.9600
C11—H110.9300C28—H28C0.9600
C12—N41.325 (5)C29—H29A0.9600
C12—H120.9300C29—H29B0.9600
C13—N31.361 (4)C29—H29C0.9600
C13—C181.406 (4)C30—H30A0.9600
C13—C141.407 (4)C30—H30B0.9600
C14—N21.376 (4)C30—H30C0.9600
C14—C151.409 (4)C31—C321.423 (7)
C15—C161.368 (4)C31—H31A0.9600
C15—H150.9300C31—H31B0.9600
C16—C171.427 (4)C31—H31C0.9600
C16—C191.502 (5)C32—N51.141 (6)
C17—C181.377 (4)Cl1—Ru12.3732 (9)
C17—C201.507 (4)F1—P11.612 (3)
C18—H180.9300F2—P11.548 (4)
C19—H19A0.9600F3—P11.555 (3)
C19—H19B0.9600F4—P11.568 (3)
C19—H19C0.9600F5—P11.550 (3)
C20—H20A0.9600F6—P11.588 (3)
C20—H20B0.9600N1—Ru12.060 (2)
C20—H20C0.9600N2—Ru12.077 (2)
C21—C221.398 (5)
N1—C1—C2121.8 (3)C25—C26—C21123.4 (3)
N1—C1—H1119.1C25—C26—Ru173.02 (17)
C2—C1—H1119.1C21—C26—Ru170.64 (18)
C3—C2—C1119.0 (3)C25—C26—H26118.3
C3—C2—H2120.5C21—C26—H26118.3
C1—C2—H2120.5Ru1—C26—H26131.1
C2—C3—C4119.8 (3)C21—C27—H27A109.5
C2—C3—H3120.1C21—C27—H27B109.5
C4—C3—H3120.1H27A—C27—H27B109.5
C3—C4—C5119.1 (3)C21—C27—H27C109.5
C3—C4—H4120.4H27A—C27—H27C109.5
C5—C4—H4120.4H27B—C27—H27C109.5
N1—C5—C4120.8 (3)C22—C28—H28A109.5
N1—C5—C6113.3 (2)C22—C28—H28B109.5
C4—C5—C6125.4 (3)H28A—C28—H28B109.5
N2—C6—C7119.7 (3)C22—C28—H28C109.5
N2—C6—C5113.4 (2)H28A—C28—H28C109.5
C7—C6—C5126.8 (3)H28B—C28—H28C109.5
N3—C7—C6122.0 (3)C24—C29—H29A109.5
N3—C7—C8115.9 (3)C24—C29—H29B109.5
C6—C7—C8121.7 (3)H29A—C29—H29B109.5
N4—C8—C9123.5 (3)C24—C29—H29C109.5
N4—C8—C7115.8 (3)H29A—C29—H29C109.5
C9—C8—C7120.4 (3)H29B—C29—H29C109.5
C8—C9—C10117.3 (4)C25—C30—H30A109.5
C8—C9—H9121.4C25—C30—H30B109.5
C10—C9—H9121.4H30A—C30—H30B109.5
C11—C10—C9119.8 (4)C25—C30—H30C109.5
C11—C10—H10120.1H30A—C30—H30C109.5
C9—C10—H10120.1H30B—C30—H30C109.5
C10—C11—C12118.0 (4)C32—C31—H31A109.5
C10—C11—H11121.0C32—C31—H31B109.5
C12—C11—H11121.0H31A—C31—H31B109.5
N4—C12—C11123.7 (4)C32—C31—H31C109.5
N4—C12—H12118.2H31A—C31—H31C109.5
C11—C12—H12118.2H31B—C31—H31C109.5
N3—C13—C18119.0 (3)N5—C32—C31178.3 (5)
N3—C13—C14121.7 (3)C1—N1—C5119.4 (3)
C18—C13—C14119.1 (3)C1—N1—Ru1124.3 (2)
N2—C14—C13119.3 (3)C5—N1—Ru1116.24 (19)
N2—C14—C15121.2 (3)C6—N2—C14118.3 (2)
C13—C14—C15119.5 (3)C6—N2—Ru1114.41 (18)
C16—C15—C14121.0 (3)C14—N2—Ru1126.31 (19)
C16—C15—H15119.5C7—N3—C13118.0 (3)
C14—C15—H15119.5C12—N4—C8117.7 (3)
C15—C16—C17119.6 (3)F2—P1—F593.3 (3)
C15—C16—C19119.8 (3)F2—P1—F392.0 (3)
C17—C16—C19120.6 (3)F5—P1—F3174.4 (3)
C18—C17—C16119.7 (3)F2—P1—F495.3 (2)
C18—C17—C20120.2 (3)F5—P1—F490.7 (2)
C16—C17—C20120.1 (3)F3—P1—F490.6 (2)
C17—C18—C13121.0 (3)F2—P1—F688.1 (2)
C17—C18—H18119.5F5—P1—F689.2 (2)
C13—C18—H18119.5F3—P1—F689.1 (2)
C16—C19—H19A109.5F4—P1—F6176.6 (2)
C16—C19—H19B109.5F2—P1—F1177.0 (2)
H19A—C19—H19B109.5F5—P1—F188.7 (2)
C16—C19—H19C109.5F3—P1—F185.9 (2)
H19A—C19—H19C109.5F4—P1—F186.91 (17)
H19B—C19—H19C109.5F6—P1—F189.68 (19)
C17—C20—H20A109.5N1—Ru1—N276.04 (9)
C17—C20—H20B109.5N1—Ru1—C2396.01 (10)
H20A—C20—H20B109.5N2—Ru1—C23152.33 (11)
C17—C20—H20C109.5N1—Ru1—C2290.94 (10)
H20A—C20—H20C109.5N2—Ru1—C22114.50 (11)
H20B—C20—H20C109.5C23—Ru1—C2238.26 (12)
C22—C21—C26117.9 (3)N1—Ru1—C21114.07 (13)
C22—C21—C27124.1 (4)N2—Ru1—C2191.16 (12)
C26—C21—C27117.9 (3)C23—Ru1—C2167.59 (13)
C22—C21—Ru170.71 (18)C22—Ru1—C2137.21 (14)
C26—C21—Ru171.11 (18)N1—Ru1—C26151.92 (11)
C27—C21—Ru1126.5 (2)N2—Ru1—C2696.24 (10)
C21—C22—C23119.0 (3)C23—Ru1—C2678.23 (11)
C21—C22—C28122.0 (3)C22—Ru1—C2667.40 (12)
C23—C22—C28119.0 (3)C21—Ru1—C2638.24 (14)
C21—C22—Ru172.09 (17)N1—Ru1—C24123.48 (11)
C23—C22—Ru170.78 (16)N2—Ru1—C24160.48 (10)
C28—C22—Ru1128.1 (2)C23—Ru1—C2437.16 (12)
C24—C23—C22123.1 (3)C22—Ru1—C2468.81 (11)
C24—C23—Ru173.31 (17)C21—Ru1—C2480.96 (13)
C22—C23—Ru170.96 (16)C26—Ru1—C2466.62 (12)
C24—C23—H23118.4N1—Ru1—C25161.15 (11)
C22—C23—H23118.4N2—Ru1—C25122.80 (11)
Ru1—C23—H23130.1C23—Ru1—C2567.07 (11)
C23—C24—C25118.0 (3)C22—Ru1—C2580.76 (11)
C23—C24—C29121.2 (3)C21—Ru1—C2568.38 (13)
C25—C24—C29120.8 (3)C26—Ru1—C2536.43 (12)
C23—C24—Ru169.53 (17)C24—Ru1—C2537.69 (13)
C25—C24—Ru171.49 (18)N1—Ru1—Cl186.79 (7)
C29—C24—Ru1128.8 (2)N2—Ru1—Cl187.99 (7)
C26—C25—C24118.6 (3)C23—Ru1—Cl1118.38 (9)
C26—C25—C30121.8 (3)C22—Ru1—Cl1156.13 (9)
C24—C25—C30119.6 (3)C21—Ru1—Cl1158.26 (10)
C26—C25—Ru170.55 (17)C26—Ru1—Cl1120.31 (9)
C24—C25—Ru170.82 (17)C24—Ru1—Cl192.79 (8)
C30—C25—Ru1128.6 (2)C25—Ru1—Cl193.98 (8)
N1—C1—C2—C31.8 (6)C14—N2—Ru1—C2411.7 (4)
C1—C2—C3—C40.0 (6)C6—N2—Ru1—C25−155.77 (19)
C2—C3—C4—C5−1.4 (5)C14—N2—Ru1—C2512.5 (3)
C3—C4—C5—N11.3 (5)C6—N2—Ru1—Cl1110.79 (19)
C3—C4—C5—C6172.5 (3)C14—N2—Ru1—Cl1−80.9 (2)
N1—C5—C6—N210.1 (3)C24—C23—Ru1—N1141.19 (19)
C4—C5—C6—N2−161.6 (3)C22—C23—Ru1—N1−83.85 (18)
N1—C5—C6—C7−173.5 (2)C24—C23—Ru1—N2−147.6 (2)
C4—C5—C6—C714.7 (5)C22—C23—Ru1—N2−12.6 (3)
N2—C6—C7—N311.2 (4)C24—C23—Ru1—C22−135.0 (3)
C5—C6—C7—N3−165.0 (3)C24—C23—Ru1—C21−105.2 (2)
N2—C6—C7—C8−161.8 (3)C22—C23—Ru1—C2129.7 (2)
C5—C6—C7—C822.1 (4)C24—C23—Ru1—C26−66.65 (19)
N3—C7—C8—N4−120.4 (3)C22—C23—Ru1—C2668.30 (19)
C6—C7—C8—N452.9 (4)C22—C23—Ru1—C24135.0 (3)
N3—C7—C8—C953.2 (4)C24—C23—Ru1—C25−30.19 (18)
C6—C7—C8—C9−133.5 (4)C22—C23—Ru1—C25104.8 (2)
N4—C8—C9—C10−1.0 (7)C24—C23—Ru1—Cl151.60 (19)
C7—C8—C9—C10−174.0 (4)C22—C23—Ru1—Cl1−173.45 (15)
C8—C9—C10—C111.0 (8)C21—C22—Ru1—N1−130.8 (2)
C9—C10—C11—C12−0.4 (8)C23—C22—Ru1—N198.54 (18)
C10—C11—C12—N4−0.2 (7)C28—C22—Ru1—N1−13.7 (3)
N3—C13—C14—N23.7 (4)C21—C22—Ru1—N2−55.7 (2)
C18—C13—C14—N2178.9 (2)C23—C22—Ru1—N2173.61 (16)
N3—C13—C14—C15−177.8 (2)C28—C22—Ru1—N261.4 (3)
C18—C13—C14—C15−2.6 (4)C21—C22—Ru1—C23130.7 (3)
N2—C14—C15—C16−179.7 (3)C28—C22—Ru1—C23−112.2 (4)
C13—C14—C15—C161.9 (4)C23—C22—Ru1—C21−130.7 (3)
C14—C15—C16—C171.1 (4)C28—C22—Ru1—C21117.1 (4)
C14—C15—C16—C19180.0 (3)C21—C22—Ru1—C2630.8 (2)
C15—C16—C17—C18−3.4 (4)C23—C22—Ru1—C26−99.85 (19)
C19—C16—C17—C18177.8 (3)C28—C22—Ru1—C26147.9 (3)
C15—C16—C17—C20175.3 (3)C21—C22—Ru1—C24103.4 (2)
C19—C16—C17—C20−3.5 (4)C23—C22—Ru1—C24−27.29 (17)
C16—C17—C18—C132.6 (4)C28—C22—Ru1—C24−139.5 (3)
C20—C17—C18—C13−176.1 (3)C21—C22—Ru1—C2566.2 (2)
N3—C13—C18—C17175.7 (3)C23—C22—Ru1—C25−64.46 (18)
C14—C13—C18—C170.3 (4)C28—C22—Ru1—C25−176.7 (3)
C26—C21—C22—C230.0 (4)C21—C22—Ru1—Cl1145.1 (2)
C27—C21—C22—C23176.5 (3)C23—C22—Ru1—Cl114.4 (3)
Ru1—C21—C22—C2354.9 (2)C28—C22—Ru1—Cl1−97.9 (3)
C26—C21—C22—C28−179.2 (3)C22—C21—Ru1—N156.0 (2)
C27—C21—C22—C28−2.7 (5)C26—C21—Ru1—N1−173.84 (17)
Ru1—C21—C22—C28−124.2 (3)C27—C21—Ru1—N1−62.6 (4)
C26—C21—C22—Ru1−55.0 (2)C22—C21—Ru1—N2131.2 (2)
C27—C21—C22—Ru1121.5 (3)C26—C21—Ru1—N2−98.63 (19)
C21—C22—C23—C24−1.6 (4)C27—C21—Ru1—N212.6 (3)
C28—C22—C23—C24177.7 (3)C22—C21—Ru1—C23−30.5 (2)
Ru1—C22—C23—C2454.0 (3)C26—C21—Ru1—C2399.6 (2)
C21—C22—C23—Ru1−55.6 (2)C27—C21—Ru1—C23−149.2 (4)
C28—C22—C23—Ru1123.6 (3)C26—C21—Ru1—C22130.1 (3)
C22—C23—C24—C251.4 (4)C27—C21—Ru1—C22−118.6 (4)
Ru1—C23—C24—C2554.4 (2)C22—C21—Ru1—C26−130.1 (3)
C22—C23—C24—C29−176.7 (3)C27—C21—Ru1—C26111.2 (4)
Ru1—C23—C24—C29−123.7 (3)C22—C21—Ru1—C24−66.7 (2)
C22—C23—C24—Ru1−53.0 (2)C26—C21—Ru1—C2463.4 (2)
C23—C24—C25—C260.3 (4)C27—C21—Ru1—C24174.7 (4)
C29—C24—C25—C26178.5 (3)C22—C21—Ru1—C25−103.7 (2)
Ru1—C24—C25—C2653.7 (2)C26—C21—Ru1—C2526.45 (18)
C23—C24—C25—C30−177.7 (3)C27—C21—Ru1—C25137.7 (4)
C29—C24—C25—C300.5 (4)C22—C21—Ru1—Cl1−141.3 (2)
Ru1—C24—C25—C30−124.2 (3)C26—C21—Ru1—Cl1−11.1 (4)
C23—C24—C25—Ru1−53.5 (2)C27—C21—Ru1—Cl1100.1 (4)
C29—C24—C25—Ru1124.7 (3)C25—C26—Ru1—N1147.8 (2)
C24—C25—C26—C21−1.9 (4)C21—C26—Ru1—N112.0 (3)
C30—C25—C26—C21176.0 (3)C25—C26—Ru1—N2−140.30 (17)
Ru1—C25—C26—C2152.0 (3)C21—C26—Ru1—N283.9 (2)
C24—C25—C26—Ru1−53.9 (2)C25—C26—Ru1—C2367.18 (18)
C30—C25—C26—Ru1124.1 (3)C21—C26—Ru1—C23−68.6 (2)
C22—C21—C26—C251.8 (5)C25—C26—Ru1—C22105.7 (2)
C27—C21—C26—C25−175.0 (3)C21—C26—Ru1—C22−30.1 (2)
Ru1—C21—C26—C25−53.0 (3)C25—C26—Ru1—C21135.8 (3)
C22—C21—C26—Ru154.8 (3)C25—C26—Ru1—C2430.00 (18)
C27—C21—C26—Ru1−122.0 (3)C21—C26—Ru1—C24−105.8 (2)
C2—C1—N1—C5−1.9 (5)C21—C26—Ru1—C25−135.8 (3)
C2—C1—N1—Ru1176.0 (3)C25—C26—Ru1—Cl1−48.97 (19)
C4—C5—N1—C10.3 (4)C21—C26—Ru1—Cl1175.25 (19)
C6—C5—N1—C1−171.9 (2)C23—C24—Ru1—N1−48.4 (2)
C4—C5—N1—Ru1−177.7 (2)C25—C24—Ru1—N1−179.10 (16)
C6—C5—N1—Ru110.1 (3)C29—C24—Ru1—N165.9 (3)
C7—C6—N2—C14−11.3 (4)C23—C24—Ru1—N2131.8 (3)
C5—C6—N2—C14165.3 (2)C25—C24—Ru1—N21.0 (4)
C7—C6—N2—Ru1157.96 (19)C29—C24—Ru1—N2−114.0 (4)
C5—C6—N2—Ru1−25.4 (3)C25—C24—Ru1—C23−130.7 (3)
C13—C14—N2—C64.3 (4)C29—C24—Ru1—C23114.2 (4)
C15—C14—N2—C6−174.1 (2)C23—C24—Ru1—C2228.03 (19)
C13—C14—N2—Ru1−163.54 (19)C25—C24—Ru1—C22−102.7 (2)
C15—C14—N2—Ru118.0 (4)C29—C24—Ru1—C22142.2 (3)
C6—C7—N3—C13−3.0 (4)C23—C24—Ru1—C2164.6 (2)
C8—C7—N3—C13170.3 (2)C25—C24—Ru1—C21−66.16 (19)
C18—C13—N3—C7−179.5 (2)C29—C24—Ru1—C21178.8 (3)
C14—C13—N3—C7−4.2 (4)C23—C24—Ru1—C26101.7 (2)
C11—C12—N4—C80.3 (6)C25—C24—Ru1—C26−29.06 (17)
C9—C8—N4—C120.3 (5)C29—C24—Ru1—C26−144.1 (3)
C7—C8—N4—C12173.7 (3)C23—C24—Ru1—C25130.7 (3)
C1—N1—Ru1—N2164.2 (3)C29—C24—Ru1—C25−115.0 (4)
C5—N1—Ru1—N2−17.92 (19)C23—C24—Ru1—Cl1−136.35 (18)
C1—N1—Ru1—C23−42.8 (3)C25—C24—Ru1—Cl192.90 (17)
C5—N1—Ru1—C23135.1 (2)C29—C24—Ru1—Cl1−22.1 (3)
C1—N1—Ru1—C22−80.8 (2)C26—C25—Ru1—N1−129.0 (3)
C5—N1—Ru1—C2297.1 (2)C24—C25—Ru1—N12.3 (4)
C1—N1—Ru1—C21−110.9 (3)C30—C25—Ru1—N1115.3 (4)
C5—N1—Ru1—C2167.0 (2)C26—C25—Ru1—N249.1 (2)
C1—N1—Ru1—C26−119.0 (3)C24—C25—Ru1—N2−179.59 (16)
C5—N1—Ru1—C2658.9 (3)C30—C25—Ru1—N2−66.6 (3)
C1—N1—Ru1—C24−15.8 (3)C26—C25—Ru1—C23−101.55 (19)
C5—N1—Ru1—C24162.13 (19)C24—C25—Ru1—C2329.79 (18)
C1—N1—Ru1—C25−17.5 (5)C30—C25—Ru1—C23142.8 (4)
C5—N1—Ru1—C25160.4 (3)C26—C25—Ru1—C22−64.20 (18)
C1—N1—Ru1—Cl175.4 (2)C24—C25—Ru1—C2267.14 (18)
C5—N1—Ru1—Cl1−106.65 (19)C30—C25—Ru1—C22−179.8 (3)
C6—N2—Ru1—N123.60 (19)C26—C25—Ru1—C21−27.67 (19)
C14—N2—Ru1—N1−168.1 (2)C24—C25—Ru1—C21103.7 (2)
C6—N2—Ru1—C23−52.4 (3)C30—C25—Ru1—C21−143.3 (4)
C14—N2—Ru1—C23115.8 (3)C24—C25—Ru1—C26131.3 (3)
C6—N2—Ru1—C22−61.0 (2)C30—C25—Ru1—C26−115.6 (4)
C14—N2—Ru1—C22107.3 (2)C26—C25—Ru1—C24−131.3 (3)
C6—N2—Ru1—C21−90.9 (2)C30—C25—Ru1—C24113.0 (4)
C14—N2—Ru1—C2177.3 (2)C26—C25—Ru1—Cl1139.24 (16)
C6—N2—Ru1—C26−128.9 (2)C24—C25—Ru1—Cl1−89.41 (17)
C14—N2—Ru1—C2639.3 (2)C30—C25—Ru1—Cl123.6 (3)
C6—N2—Ru1—C24−156.5 (3)
Acknowledgements top

This work was supported by the Swiss National Science Foundation.

references
References top

Baumann, F., Stange, A. & Kaim, W. (1998). Inorg. Chem. Commun. 1, 305–308.

Berg, D. J., Boncella, J. M. & Andersen, R. A. (2002). Organometallics, 21, 4622–4631.

Canivet, J., Karmazin-Brelot, L. & Süss-Fink, G. (2005). J. Organomet. Chem. 690, 3202–3211.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Lalrempuia, R. & Kollipara, M. R. (2003). Polyhedron, 22, 3155–3160.

Scott, S. M., Gordon, K. C. & Burrell, A. K. (1999). J. Chem. Soc. Dalton Trans. pp. 2669–2673.

Sheldrick, G. M. (2001). SHELXTL. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.

Singh, A., Singh, N. & Pandey, D. S. (2002). J. Organomet. Chem. 642, 48–57.

Stoe (2000). EXPOSE, CELL and INTEGRATE. Stoe & Cie, Darmstadt, Germany.

Therrien, B., Süss-Fink, G., Govindaswamy, P. & Saïd-Mohamed, C. (2007). Polyhedron In the press.

Wozniak, K., Krygowski, T. M., Grech, E., Kolodziejski, W. & Klinowski, J. (1993). J. Phys. Chem. 97, 1862–1867.