supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportcited insimilar papers Open access

Acta Cryst. (2008). E64, m1568    [ doi:10.1107/S1600536808037689 ]

([eta]5-Pentamethylcyclopentadienyl)([eta]6-p-toluenesulfonamide)ruthenium(II) tetraphenylborate

B. T. Loughrey, M. L. Williams, S.-A. Poulsen and P. C. Healy

Abstract top

The crystal structure of the title compound, [Ru(C10H15)(C7H9NO2S)]C24H20B, has been determined as part of our investigation into the structural and biological properties of organometallic RuII-arene-Cp* complex salts of the type [R-PhRuCp*]+·X- (where Cp* is pentamethylcyclopentadiene). Tethering the RuCp* group to the benzene ring of p-toluenesulfonamide results in only minor changes to the molecular geometry of the sulfonamide, but, together with crystallization as the [BPh4]- salt, effectively blocks involvement of the sulfonamide group in N-H...O hydrogen-bonding networks.

Comment top

As part of our investigation into the synthesis, structural characterization and biological properties of ionic Ru(II) organometallic complexes [R-PhRuCp*]X (Loughrey et al., 2008), we have prepared and characterized the tetraphenylborate salt of the organometallic sandwich compound of RuCp* and p-toluenesulfonamide, (I), and determined its crystal structure (Fig. 1). While covalent bonding of ruthenocene to sulfonamides has been reported previously (Salmon et al., 2007), this is the first recorded synthesis and structure determination of a ruthenium based organometallic sulfonamide where the metal has been tethered directly to an aromatic sulfonamide pharmacaphore.

The compound was prepared in 75% yield through the reaction of RuCl3.xH2O with an excess of the aromatic sulfonamide ligand in ethanol. This prompts formation of the labile chlorido-bridged dimer which can undertake ligand exchange of the µ-Cl ligands with a Cp* ligand and formation of the cation which can be readily isolated as the tetraphenylborate salt through addition of an aqueous solution of sodium tetraphenylborate (Fig. 2).

The structural parameters of the cation in (I) are similar to those reported for other [(arene)RuCp*]+ complexes (Gemel et al., 1996; Navarro Clemente et al., 2002; Loughrey et al., 2008) with Ru—C distances of 2.177 (4)–2.196 (3) Å (Cp*) and 2.193 (3)–2.240 (3) Å (Ph). The average value of 1.41 (1) Å for the C—C bond lengths in the benzene ring is 0.02Å longer than the average of 1.39 (1) Å observed for the parent sulfonamide (Zerbe et al., 2005), while the bond lengths in the SO2NH2 groups do not differ significantly. As illustrated in Fig. 1, the S═O bonds are directed towards, and the NH2 group away, from the Cp* ring with torsion angles O1—S1—C11—C12 16.0 (2)°, O2—S1—C11—C16 -31.7 (2)° and N1—S1—C11—C16 82.9 (2)°. A feature of the present structure is the complete blocking, by the Cp* group and the [BPh4]- anion, of the N—H···O hydrogen bonding networks that are characteristic of other structural studies of the sulfonamide (Zerbe et al., 2005; Ferguson & Glidewell, 1988).

Comparison of the 1H NMR spectra for (I) and its parent sulfonamide shows the aromatic protons to experience an upfield shift of ca 1.5 p.p.m. which can be attributed to the presence of the diamagnetic Ru(II) shielding the nuclei of the aromatic protons. The sulfonamide protons experience a downfield shift of 0.49 p.p.m. which is also attributable to the loss of electron density from the sulfonamide group due to π-donor backbonding of the ligand with the d-orbitals of the metal (Moreno et al., 2008).

Related literature top

For related literature, see: Navarro Clemente et al. (2002); Ferguson & Glidewell (1988); Gemel et al. (1996); Loughrey et al. (2008); Moreno et al. (2008); Salmon et al. (2007); Zerbe et al. (2005).

Experimental top

4-Methylbenzenesulfonamide (1.04 g, 6.08 mmol) was added to a solution of ruthenium trichloride hydrate (0.20 g) in ethanol (20 ml) under argon. The resulting solution was refluxed for a period of 10 h to give a dark blue solution. Pentamethylcyclopentadiene (Cp*, 0.3 ml, 1.88 mmol) was added to solution and the mixture refluxed for a further 10 h. The solvent was concentrated in vacuo with the remaining residue being redissolved in an ether/water partition (20 ml/20 ml). The aqueous portion was retained and washed with a further three aliquots of diethyl ether (20 ml). The aqueous layer was then mixed slowly with an aqueous solution of sodium tetraphenylborate (5 ml, 0.30 M). The resulting precipitate was filtered from solution and redissolved in a minimum volume of acetone. This solution was filtered through a short alumina column (neutral, 150 mesh) using acetone as the eluent. The solution was concentrated in vacuo and the product was recrystallized through addition of a minimum quantity of cold water. The resulting crystalline precipitate was then filtered from solution and dried in vacuo. Yield = 0.409 g, 75%. Crystals suitable for X-ray diffraction studies were grown from a saturated solution of methanol following slow diffusion with diethyl ether. M.p. 245°C (decomp). Analysis: Calcd for C41H44O2NSBRu: C 67.8, H 6.11, N 1.93, S 4.41%. Found C 67.4, H 5.87, N 1.92, S 4.68%.

1H NMR (400 MHz, d6-DMSO, 298 K), δ p.p.m. 1.88 (s, 15H, C5(C5H15)), 2.19 (s, 3H, CH3), 6.03–6.05 (m, 2H, C6H4 ortho), 6.21–6.23 (m, 2H, C6H4 meta), 6.75–6.80 (m, 4H, B(C6H5)4 para), 6.88–6.93 (m, 8H, B(C6H5)4 meta), 7.14–7.19 (m, 8H, B(C6H5)4 ortho), 7.85 (s, 2H, SO2NH2). 13C{1H} NMR (100 MHz, d6-DMSO), δ p.p.m. 9.69 (C5(C5H15)), 17.35 (CH3), 84.11 (2CH, aromatic), 87.85 (2CH, aromatic), 97.14 (C5(C5H15)), 101.70 (C—CH3), 104.69 (C—SO2NH2), 121.48 (4CH, B(C6H5)4), 125.28 (8CH, B(C6H5)4), 135.50 (8CH, B(C6H5)4), 162.35, 163.01, 163.65, 164.31 (4CH, B(C6H5)4, signals split by 11B). ESMS (m/z): +ve ion, calcd m/z for [(η5-C5(CH3)5)Ru (η6-CH3C6H4SO2NH2)+]: 407.56, found: 407.98 (100%), -ve ion, calcd m/z for B(C6H5)4-: 319.25, found: 319.11 (100%).

Refinement top

H atoms attached to carbon were constrained as riding atoms, with C—H set to 0.94–96 Å. Uiso(H) values were set to 1.2Ueq (aromatic) and 1.5Ueq (alkyl) of the parent atom. The N protons were located in Fourier difference maps and constrained as riding atoms with N—H set to 0.86Å and Uiso(H) values set to 1.2Ueq of the parent atom.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The structure of (I), with atom labels and 30% probability displacement ellipsoids for the non-H atoms.
[Figure 2] Fig. 2. Synthetic route for (I).
(η5-Pentamethylcyclopentadienyl)(η6-p- toluenesulfonamide)ruthenium(II) tetraphenylborate top
Crystal data top
[Ru(C10H15)(C7H9NO2S)]C24H20BF(000) = 1512
Mr = 726.72Dx = 1.318 Mg m−3
Monoclinic, P21/nMelting point: 518 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71070 Å
a = 12.2254 (2) ÅCell parameters from 9519 reflections
b = 13.4685 (2) Åθ = 3.1–27.5°
c = 22.9204 (5) ŵ = 0.52 mm−1
β = 104.000 (2)°T = 296 K
V = 3661.92 (12) Å3Block, brown
Z = 40.43 × 0.30 × 0.23 mm
Data collection top
Oxford-Diffraction GEMINI S Ultra
diffractometer		8151 independent reflections
Radiation source: Enhance (Mo) X-ray Source6209 reflections with I > 2σ(I)
graphiteRint = 0.024
Detector resolution: 16.0774 pixels mm-1θmax = 27.6°, θmin = 3.1°
ω and φ scansh = −15→15
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		k = −15→17
Tmin = 0.807, Tmax = 0.890l = −29→29
17618 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0489P)2 + 0.272P]
where P = (Fo2 + 2Fc)/3
8151 reflections(Δ/σ)max = 0.007
430 parametersΔρmax = 0.51 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
0 constraints
Crystal data top
[Ru(C10H15)(C7H9NO2S)]C24H20BV = 3661.92 (12) Å3
Mr = 726.72Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.2254 (2) ŵ = 0.52 mm−1
b = 13.4685 (2) ÅT = 296 K
c = 22.9204 (5) Å0.43 × 0.30 × 0.23 mm
β = 104.000 (2)°
Data collection top
Oxford-Diffraction GEMINI S Ultra
diffractometer		8151 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		6209 reflections with I > 2σ(I)
Tmin = 0.807, Tmax = 0.890Rint = 0.024
17618 measured reflectionsθmax = 27.6°
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.089Δρmax = 0.51 e Å−3
S = 1.04Δρmin = −0.29 e Å−3
8151 reflectionsAbsolute structure: ?
430 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ru10.38014 (1)−0.21168 (1)0.17469 (1)0.0365 (1)
S10.35157 (5)0.04626 (5)0.20161 (3)0.0456 (2)
O10.23845 (15)0.05536 (15)0.16834 (11)0.0647 (7)
O20.37719 (18)0.02787 (14)0.26438 (9)0.0627 (7)
N10.41631 (19)0.14599 (16)0.19196 (11)0.0542 (8)
C10.2334 (2)−0.2331 (2)0.21247 (17)0.0621 (12)
C20.2250 (3)−0.2969 (3)0.16296 (16)0.0739 (11)
C30.3198 (3)−0.3637 (2)0.17651 (14)0.0624 (10)
C40.3851 (2)−0.33851 (19)0.23507 (12)0.0485 (8)
C50.3308 (2)−0.2584 (2)0.25647 (12)0.0478 (8)
C60.1483 (3)−0.1551 (3)0.2193 (2)0.116 (2)
C70.1288 (4)−0.3003 (4)0.1069 (2)0.152 (3)
C80.3394 (6)−0.4492 (3)0.1387 (2)0.134 (3)
C90.4877 (3)−0.3916 (3)0.26950 (18)0.0806 (13)
C100.3661 (3)−0.2137 (2)0.31759 (16)0.0789 (14)
C110.41167 (19)−0.05235 (17)0.16787 (11)0.0392 (7)
C120.35855 (19)−0.08679 (18)0.11030 (11)0.0448 (8)
C130.4059 (2)−0.1674 (2)0.08548 (11)0.0467 (8)
C140.5055 (2)−0.21405 (19)0.11782 (11)0.0448 (8)
C150.55828 (18)−0.17788 (19)0.17584 (11)0.0424 (7)
C160.51260 (18)−0.09737 (17)0.20122 (11)0.0387 (7)
C170.5543 (3)−0.3003 (2)0.09141 (14)0.0656 (11)
C180.5435 (2)0.22539 (17)0.08062 (10)0.0395 (7)
C190.5006 (2)0.14069 (19)0.04764 (12)0.0488 (8)
C200.3856 (2)0.1250 (2)0.02495 (13)0.0585 (10)
C210.3083 (2)0.1934 (2)0.03360 (14)0.0597 (10)
C220.3467 (2)0.2793 (2)0.06503 (13)0.0523 (9)
C230.4607 (2)0.29397 (18)0.08782 (12)0.0472 (8)
C240.68445 (19)0.24180 (18)0.18620 (11)0.0401 (7)
C250.7050 (2)0.15665 (19)0.22291 (11)0.0470 (8)
C260.6928 (2)0.1559 (2)0.28160 (12)0.0570 (9)
C270.6609 (2)0.2409 (3)0.30692 (12)0.0601 (9)
C280.6447 (2)0.3258 (2)0.27362 (12)0.0565 (9)
C290.6569 (2)0.3257 (2)0.21496 (12)0.0478 (8)
C300.7594 (2)0.15911 (19)0.09208 (11)0.0445 (8)
C310.7530 (3)0.0572 (2)0.10306 (12)0.0551 (9)
C320.8262 (3)−0.0124 (2)0.08709 (15)0.0724 (13)
C330.9071 (3)0.0175 (3)0.05938 (18)0.0859 (16)
C340.9148 (3)0.1154 (3)0.04638 (18)0.0844 (16)
C350.8420 (3)0.1854 (2)0.06196 (14)0.0609 (10)
C360.7198 (2)0.35392 (18)0.09646 (10)0.0414 (7)
C370.6609 (2)0.41396 (19)0.04952 (12)0.0521 (9)
C380.7036 (3)0.5030 (2)0.03422 (14)0.0664 (11)
C390.8096 (3)0.5350 (2)0.06544 (16)0.0697 (11)
C400.8697 (3)0.4785 (2)0.11235 (16)0.0646 (11)
C410.8253 (2)0.3907 (2)0.12730 (12)0.0502 (8)
B10.6782 (2)0.2436 (2)0.11327 (12)0.0396 (8)
H10.407100.157200.154100.0640*
H20.487100.139800.208500.0640*
H6A0.10370−0.136600.180300.1740*
H6B0.18710−0.097800.239000.1740*
H6C0.10010−0.181400.243000.1740*
H7A0.06640−0.335900.115400.2280*
H7B0.15350−0.333400.075200.2280*
H7C0.10580−0.233900.094500.2280*
H8A0.41880−0.462400.146400.2000*
H8B0.31070−0.433200.097000.2000*
H8C0.30130−0.506900.148500.2000*
H9A0.53480−0.346100.296700.1210*
H9B0.52860−0.417700.242100.1210*
H9C0.46560−0.445100.291900.1210*
H10A0.34900−0.144000.315300.1180*
H10B0.44580−0.222800.333100.1180*
H10C0.32640−0.245400.343800.1180*
H120.29130−0.056000.087900.0530*
H130.36930−0.191000.046700.0580*
H150.62520−0.208900.198100.0520*
H160.54930−0.073000.239800.0480*
H17A0.49440−0.340200.068200.0980*
H17B0.59940−0.339700.123200.0980*
H17C0.60040−0.276200.066000.0980*
H190.552200.091900.040400.0610*
H200.360300.065200.003400.0700*
H210.230000.182800.017800.0730*
H220.294000.327200.071400.0630*
H230.484700.354000.109100.0570*
H250.728100.097700.206700.0580*
H260.706200.096800.304600.0690*
H270.650600.240200.346800.0720*
H280.625100.385700.290700.0700*
H290.646300.386800.193200.0570*
H310.696300.033900.121800.0670*
H320.81760−0.080900.095600.0880*
H330.95810−0.029300.049800.1060*
H340.970300.137100.027100.1050*
H350.849500.252200.051700.0740*
H370.588700.393200.027800.0620*
H380.660500.541500.002900.0780*
H390.839000.595400.053800.0860*
H400.941900.499500.134500.0760*
H410.867500.353400.160200.0630*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.0329 (1)0.0389 (1)0.0379 (1)−0.0008 (1)0.0089 (1)0.0034 (1)
S10.0425 (3)0.0405 (3)0.0594 (4)0.0037 (3)0.0231 (3)0.0046 (3)
O10.0412 (9)0.0597 (12)0.0951 (16)0.0079 (9)0.0205 (10)−0.0026 (11)
O20.0820 (13)0.0559 (12)0.0603 (13)0.0125 (10)0.0367 (11)0.0065 (9)
N10.0574 (12)0.0420 (12)0.0680 (15)−0.0022 (10)0.0243 (11)0.0044 (11)
C10.0398 (13)0.0571 (18)0.095 (3)−0.0028 (12)0.0271 (15)0.0244 (16)
C20.0550 (16)0.081 (2)0.073 (2)−0.0356 (17)−0.0092 (15)0.0294 (18)
C30.087 (2)0.0449 (15)0.0618 (19)−0.0228 (15)0.0308 (16)−0.0053 (13)
C40.0463 (13)0.0450 (14)0.0563 (16)−0.0011 (11)0.0167 (12)0.0145 (12)
C50.0509 (14)0.0463 (14)0.0538 (16)−0.0089 (11)0.0277 (12)0.0026 (12)
C60.0615 (19)0.093 (3)0.218 (5)0.027 (2)0.082 (3)0.059 (3)
C70.111 (3)0.196 (6)0.110 (4)−0.096 (4)−0.050 (3)0.060 (4)
C80.262 (7)0.061 (2)0.104 (4)−0.052 (3)0.095 (4)−0.038 (2)
C90.0648 (18)0.079 (2)0.101 (3)0.0155 (17)0.0260 (18)0.040 (2)
C100.110 (3)0.075 (2)0.067 (2)−0.031 (2)0.051 (2)−0.0106 (17)
C110.0377 (11)0.0360 (12)0.0475 (14)0.0003 (9)0.0174 (10)0.0048 (10)
C120.0390 (11)0.0497 (14)0.0459 (14)0.0015 (11)0.0104 (10)0.0120 (11)
C130.0471 (13)0.0575 (15)0.0354 (13)−0.0010 (12)0.0097 (10)0.0018 (11)
C140.0440 (12)0.0496 (14)0.0447 (14)0.0022 (11)0.0182 (10)−0.0006 (11)
C150.0329 (10)0.0499 (13)0.0457 (14)0.0031 (10)0.0123 (10)0.0016 (11)
C160.0335 (10)0.0438 (13)0.0400 (13)−0.0021 (10)0.0113 (9)0.0037 (10)
C170.0694 (18)0.073 (2)0.0566 (18)0.0138 (15)0.0194 (15)−0.0141 (15)
C180.0465 (12)0.0375 (13)0.0334 (12)−0.0011 (10)0.0077 (10)0.0046 (9)
C190.0549 (14)0.0449 (14)0.0452 (15)0.0000 (12)0.0093 (11)−0.0019 (11)
C200.0587 (15)0.0559 (17)0.0557 (18)−0.0139 (14)0.0035 (13)−0.0080 (13)
C210.0483 (14)0.068 (2)0.0575 (18)−0.0106 (14)0.0025 (13)0.0068 (14)
C220.0490 (13)0.0517 (15)0.0555 (17)0.0079 (12)0.0114 (12)0.0108 (13)
C230.0514 (13)0.0414 (13)0.0467 (14)0.0003 (11)0.0078 (11)0.0044 (11)
C240.0362 (11)0.0464 (13)0.0369 (13)−0.0023 (10)0.0076 (9)−0.0011 (10)
C250.0472 (13)0.0493 (15)0.0436 (14)−0.0048 (11)0.0092 (11)0.0044 (11)
C260.0524 (14)0.0715 (19)0.0458 (15)−0.0149 (14)0.0093 (12)0.0136 (14)
C270.0440 (13)0.100 (2)0.0401 (15)−0.0072 (15)0.0176 (12)0.0020 (15)
C280.0446 (13)0.084 (2)0.0426 (15)0.0038 (14)0.0136 (11)−0.0126 (14)
C290.0467 (13)0.0539 (14)0.0429 (14)0.0033 (12)0.0108 (11)0.0001 (12)
C300.0503 (13)0.0464 (14)0.0332 (12)0.0067 (11)0.0032 (10)−0.0049 (10)
C310.0695 (17)0.0480 (15)0.0430 (15)0.0075 (13)0.0042 (13)−0.0039 (12)
C320.104 (3)0.0500 (17)0.0499 (18)0.0252 (17)−0.0072 (17)−0.0110 (14)
C330.095 (3)0.090 (3)0.073 (2)0.038 (2)0.021 (2)−0.021 (2)
C340.081 (2)0.098 (3)0.084 (3)0.013 (2)0.039 (2)−0.021 (2)
C350.0679 (17)0.0652 (18)0.0538 (17)0.0046 (14)0.0227 (14)−0.0102 (14)
C360.0491 (12)0.0391 (13)0.0374 (13)0.0001 (10)0.0132 (10)−0.0032 (10)
C370.0621 (15)0.0479 (15)0.0449 (15)−0.0038 (13)0.0102 (12)0.0036 (12)
C380.096 (2)0.0490 (16)0.0559 (19)−0.0016 (16)0.0220 (17)0.0105 (14)
C390.101 (2)0.0458 (16)0.071 (2)−0.0191 (17)0.038 (2)−0.0041 (15)
C400.0671 (17)0.0595 (18)0.072 (2)−0.0203 (15)0.0264 (16)−0.0159 (16)
C410.0513 (13)0.0521 (15)0.0476 (15)−0.0041 (12)0.0127 (12)−0.0036 (12)
B10.0445 (13)0.0385 (13)0.0343 (14)0.0006 (11)0.0069 (11)0.0003 (11)
Geometric parameters (Å, °) top
Ru1—C12.192 (3)C16—H160.9500
Ru1—C22.177 (4)C17—H17A0.9600
Ru1—C32.180 (3)C17—H17B0.9600
Ru1—C42.190 (3)C17—H17C0.9600
Ru1—C52.196 (3)C18—C191.399 (3)
Ru1—C112.193 (2)C18—C231.409 (3)
Ru1—C122.211 (2)C18—B11.654 (4)
Ru1—C132.224 (2)C19—C201.392 (4)
Ru1—C142.240 (3)C20—C211.368 (4)
Ru1—C152.219 (2)C21—C221.384 (4)
Ru1—C162.211 (2)C22—C231.379 (4)
S1—O11.414 (2)C24—C251.409 (4)
S1—O21.418 (2)C24—C291.390 (4)
S1—N11.601 (2)C24—B11.655 (4)
S1—C111.782 (2)C25—C261.389 (4)
N1—H20.8600C26—C271.382 (5)
N1—H10.8600C27—C281.362 (5)
C1—C51.404 (4)C28—C291.388 (4)
C1—C21.407 (5)C30—C311.401 (4)
C1—C61.513 (5)C30—C351.400 (4)
C2—C31.441 (5)C30—B11.658 (4)
C2—C71.518 (6)C31—C321.404 (5)
C3—C81.495 (5)C32—C331.359 (5)
C3—C41.427 (4)C33—C341.360 (6)
C4—C51.415 (4)C34—C351.401 (5)
C4—C91.493 (5)C36—C371.398 (4)
C5—C101.490 (4)C36—C411.403 (4)
C11—C161.421 (3)C36—B11.646 (4)
C11—C121.401 (3)C37—C381.386 (4)
C12—C131.413 (4)C38—C391.389 (5)
C13—C141.411 (4)C39—C401.376 (5)
C14—C151.417 (3)C40—C411.379 (4)
C14—C171.499 (4)C19—H190.9500
C15—C161.408 (3)C20—H200.9600
C6—H6A0.9600C21—H210.9500
C6—H6B0.9600C22—H220.9500
C6—H6C0.9600C23—H230.9500
C7—H7A0.9600C25—H250.9500
C7—H7B0.9600C26—H260.9500
C7—H7C0.9600C27—H270.9500
C8—H8A0.9600C28—H280.9500
C8—H8B0.9600C29—H290.9500
C8—H8C0.9600C31—H310.9500
C9—H9A0.9600C32—H320.9500
C9—H9B0.9600C33—H330.9500
C9—H9C0.9600C34—H340.9400
C10—H10A0.9600C35—H350.9400
C10—H10B0.9600C37—H370.9400
C10—H10C0.9600C38—H380.9400
C12—H120.9500C39—H390.9500
C13—H130.9500C40—H400.9500
C15—H150.9500C41—H410.9500
S1···H6B3.0600C23···H372.6800
O1···C63.352 (5)C23···H12.5700
O1···C5i3.269 (3)C24···H233.0500
O1···C10i3.408 (4)C24···H412.8800
O1···C4i3.293 (3)C24···H22.9300
O2···C2i3.303 (4)C25···H312.8300
O2···C3i3.369 (4)C25···H22.6100
O1···H6B2.7900C25···H15v3.0100
O1···H10Ci2.7900C26···H15v2.8300
O1···H122.5800C26···H22.6700
O1···H9Ci2.8600C26···H17Bv2.9200
O2···H162.6800C27···H15v2.7300
O2···H6B2.8200C27···H23.0200
O2···H10A2.6500C28···H15v2.7700
O2···H40ii2.8200C28···H6Ci2.9300
N1···C223.349 (4)C29···H232.8300
N1···C233.254 (3)C29···H15v2.9500
N1···C253.431 (3)C30···H252.8700
N1···H6Ci2.7900C30···H192.6800
C1···C32.304 (4)C31···H252.5300
C1···C42.293 (4)C31···H192.5700
C1···C72.610 (6)C31···H20iv2.9900
C1···C102.572 (5)C32···H20iv2.7800
C1···C113.578 (4)C32···H28ii3.0500
C2···C42.305 (5)C36···H352.5000
C2···C52.279 (4)C36···H292.6200
C2···C62.604 (6)C36···H232.9600
C2···C82.617 (7)C37···H17Aiv3.0600
C2···O2iii3.303 (4)C37···H232.9300
C3···C12.304 (4)C40···H26v2.8100
C3···C52.295 (4)C41···H292.9400
C3···C72.632 (6)C41···H16v3.1000
C3···C92.604 (5)C41···H352.6100
C3···C143.536 (4)H1···C192.9400
C3···O2iii3.369 (4)H1···C182.8000
C4···C12.293 (4)H1···C222.5900
C4···C22.305 (5)H1···C202.9400
C4···C82.611 (5)H1···C212.7800
C4···C102.583 (4)H1···C232.5700
C4···C153.521 (4)H2···C252.6100
C4···O1iii3.293 (3)H2···C262.6700
C5···C22.279 (4)H2···C242.9300
C5···C32.295 (4)H2···C273.0200
C5···C62.592 (5)H6A···H7C2.3700
C5···C92.590 (5)H6A···C72.8300
C5···C163.551 (3)H6B···O22.8200
C5···O1iii3.269 (3)H6B···C102.9300
C6···O13.352 (5)H6B···H10A2.3900
C10···O1iii3.408 (4)H6B···S13.0600
C11···C13.578 (4)H6B···O12.7900
C11···C132.431 (3)H6C···N1iii2.7900
C11···C152.438 (3)H6C···C28iii2.9300
C11···C142.831 (3)H7B···C82.8500
C12···C142.459 (4)H7B···H8B2.3000
C12···S12.772 (3)H7C···H6A2.3700
C12···C203.519 (4)H7C···C62.9800
C12···C152.819 (3)H8A···C92.9000
C12···C162.452 (3)H8A···H9B2.3600
C13···C112.431 (3)H8B···H7B2.3000
C13···C152.432 (3)H8B···C72.9100
C13···C19iv3.526 (4)H9A···H10B2.2500
C13···C162.820 (3)H9A···C102.8500
C13···C172.529 (4)H9B···C82.9100
C14···C162.460 (3)H9B···H8A2.3600
C14···C122.459 (4)H9C···O1iii2.8600
C14···C112.831 (3)H10A···O22.6500
C14···C33.536 (4)H10A···C62.8800
C15···C112.438 (3)H10A···H6B2.3900
C15···C43.521 (4)H10B···C92.8100
C15···C132.432 (3)H10B···H41ii2.4700
C15···C172.534 (4)H10B···H9A2.2500
C15···C28ii3.535 (3)H10C···O1iii2.7900
C15···C122.819 (3)H12···O12.5800
C15···C27ii3.533 (4)H13···H17A2.5000
C16···C122.452 (3)H13···C19iv3.0500
C16···C142.460 (3)H15···H17B2.4300
C16···C132.820 (3)H15···C27ii2.7300
C16···S12.762 (2)H15···C28ii2.7700
C16···C53.551 (3)H15···C29ii2.9500
C19···C313.241 (4)H15···C25ii3.0100
C19···C13iv3.526 (4)H15···C26ii2.8300
C20···C32iv3.519 (4)H16···H41ii2.4800
C20···C123.519 (4)H16···O22.6800
C22···N13.349 (4)H16···C41ii3.1000
C23···C293.324 (4)H17A···H37iv2.3000
C23···N13.254 (3)H17A···H132.5000
C23···C373.227 (4)H17A···C37iv3.0600
C25···N13.431 (3)H17B···H152.4300
C25···C313.235 (4)H17B···C26ii2.9200
C27···C15v3.533 (4)H17C···C21iv2.9900
C28···C15v3.535 (3)H17C···C20iv2.9500
C29···C233.324 (4)H19···C302.6800
C29···C413.323 (4)H19···C312.5700
C31···C193.241 (4)H19···H312.3700
C31···C253.235 (4)H20···C31iv2.9900
C32···C20iv3.519 (4)H20···C32iv2.7800
C35···C413.175 (4)H23···C243.0500
C37···C233.227 (4)H23···C292.8300
C41···C293.323 (4)H23···C362.9600
C41···C353.175 (4)H23···C372.9300
C6···H10A2.8800H23···H292.4400
C6···H7C2.9800H23···H372.5500
C7···H8B2.9100H25···C302.8700
C7···H6A2.8300H25···C312.5300
C8···H9B2.9100H25···H312.0800
C8···H7B2.8500H26···C40ii2.8100
C9···H8A2.9000H28···C32v3.0500
C9···H10B2.8100H28···H32v2.5700
C10···H9A2.8500H29···C362.6200
C10···H6B2.9300H29···C412.9400
C11···H162.0700H29···H232.4400
C11···H122.0500H31···C192.9500
C12···H132.0500H31···C252.8300
C13···H122.0600H31···H192.3700
C14···H152.0600H31···H252.0800
C14···H132.0500H32···H28ii2.5700
C15···H162.0600H33···H34vii2.5900
C16···H152.0500H34···H33vii2.5900
C18···H12.8000H35···C362.5000
C18···H372.6800H35···C412.6100
C19···H312.9500H37···C182.6800
C19···H13iv3.0500H37···C232.6800
C19···H12.9400H37···H232.5500
C20···H17Civ2.9500H37···H17Aiv2.3000
C20···H12.9400H38···C22vi2.8600
C21···H17Civ2.9900H40···O2v2.8200
C21···H12.7800H41···C242.8800
C22···H12.5900H41···H10Bv2.4700
C22···H38vi2.8600H41···H16v2.4800
C1—Ru1—C237.58 (13)H6A—C6—H6C110.00
C1—Ru1—C363.62 (12)H6B—C6—H6C109.00
C1—Ru1—C463.12 (10)C2—C7—H7A110.00
C1—Ru1—C537.32 (11)C2—C7—H7B109.00
C1—Ru1—C11109.38 (9)C2—C7—H7C110.00
C1—Ru1—C12112.77 (10)H7A—C7—H7B109.00
C1—Ru1—C13135.24 (11)H7A—C7—H7C110.00
C1—Ru1—C14165.69 (11)H7B—C7—H7C109.00
C1—Ru1—C15156.52 (11)C3—C8—H8A109.00
C1—Ru1—C16126.74 (10)C3—C8—H8B109.00
C2—Ru1—C338.61 (14)C3—C8—H8C109.00
C2—Ru1—C463.70 (12)H8A—C8—H8B110.00
C2—Ru1—C562.82 (12)H8A—C8—H8C109.00
C2—Ru1—C11132.08 (12)H8B—C8—H8C109.00
C2—Ru1—C12111.04 (12)C4—C9—H9A109.00
C2—Ru1—C13109.92 (11)C4—C9—H9B110.00
C2—Ru1—C14128.25 (12)C4—C9—H9C109.00
C2—Ru1—C15158.89 (12)H9A—C9—H9B109.00
C2—Ru1—C16163.63 (12)H9A—C9—H9C109.00
C3—Ru1—C438.11 (11)H9B—C9—H9C109.00
C3—Ru1—C563.28 (11)C5—C10—H10A110.00
C3—Ru1—C11170.65 (11)C5—C10—H10B109.00
C3—Ru1—C12137.82 (10)C5—C10—H10C109.00
C3—Ru1—C13113.16 (11)H10A—C10—H10B109.00
C3—Ru1—C14106.27 (11)H10A—C10—H10C109.00
C3—Ru1—C15121.88 (12)H10B—C10—H10C109.00
C3—Ru1—C16151.35 (11)Ru1—C12—H12130.00
C4—Ru1—C537.65 (10)C11—C12—H12120.00
C4—Ru1—C11146.09 (9)C13—C12—H12120.00
C4—Ru1—C12174.73 (9)Ru1—C13—H13129.00
C4—Ru1—C13143.29 (10)C12—C13—H13119.00
C4—Ru1—C14116.01 (9)C14—C13—H13120.00
C4—Ru1—C15105.99 (9)Ru1—C15—H15129.00
C4—Ru1—C16117.58 (9)C14—C15—H15119.00
C5—Ru1—C11115.51 (10)C16—C15—H15120.00
C5—Ru1—C12140.79 (9)Ru1—C16—H16130.00
C5—Ru1—C13172.28 (9)C11—C16—H16120.00
C5—Ru1—C14149.41 (9)C15—C16—H16120.00
C5—Ru1—C15121.35 (9)C14—C17—H17A109.00
C5—Ru1—C16107.40 (9)C14—C17—H17B109.00
C11—Ru1—C1237.11 (9)C14—C17—H17C109.00
C11—Ru1—C1366.77 (9)H17A—C17—H17B109.00
C11—Ru1—C1479.37 (9)H17A—C17—H17C110.00
C11—Ru1—C1567.11 (9)H17B—C17—H17C109.00
C11—Ru1—C1637.64 (9)C19—C18—C23114.3 (2)
C12—Ru1—C1337.16 (9)C19—C18—B1124.6 (2)
C12—Ru1—C1467.07 (9)C23—C18—B1121.0 (2)
C12—Ru1—C1579.06 (9)C18—C19—C20122.6 (2)
C12—Ru1—C1667.35 (9)C19—C20—C21121.0 (3)
C13—Ru1—C1436.85 (9)C20—C21—C22118.6 (2)
C13—Ru1—C1566.36 (9)C21—C22—C23120.1 (2)
C13—Ru1—C1678.98 (9)C18—C23—C22123.4 (2)
C14—Ru1—C1537.05 (9)C25—C24—C29114.0 (2)
C14—Ru1—C1667.11 (9)C25—C24—B1125.0 (2)
C15—Ru1—C1637.08 (9)C29—C24—B1120.7 (2)
O1—S1—O2120.63 (14)C24—C25—C26122.6 (2)
O1—S1—N1107.73 (13)C25—C26—C27120.5 (3)
O1—S1—C11106.42 (12)C26—C27—C28118.5 (2)
O2—S1—N1106.94 (13)C27—C28—C29120.4 (3)
O2—S1—C11107.28 (12)C24—C29—C28123.7 (2)
N1—S1—C11107.20 (12)C31—C30—C35114.5 (3)
H1—N1—H2109.00C31—C30—B1123.8 (2)
S1—N1—H1110.00C35—C30—B1121.7 (2)
S1—N1—H2110.00C30—C31—C32122.7 (3)
Ru1—C1—C270.7 (2)C31—C32—C33120.4 (3)
C2—C1—C6126.1 (3)C32—C33—C34119.1 (3)
C5—C1—C6125.4 (3)C33—C34—C35121.0 (3)
Ru1—C1—C6126.8 (2)C30—C35—C34122.3 (3)
C2—C1—C5108.4 (3)C37—C36—C41115.0 (2)
Ru1—C1—C571.50 (15)C37—C36—B1124.9 (2)
Ru1—C2—C171.77 (19)C41—C36—B1120.0 (2)
Ru1—C2—C370.8 (2)C36—C37—C38122.7 (3)
C3—C2—C7125.6 (3)C37—C38—C39120.0 (3)
C1—C2—C7126.3 (4)C38—C39—C40119.1 (3)
Ru1—C2—C7126.4 (3)C39—C40—C41120.1 (3)
C1—C2—C3108.0 (3)C36—C41—C40123.2 (3)
Ru1—C3—C270.59 (19)C20—C19—H19119.00
Ru1—C3—C471.33 (16)C18—C19—H19119.00
Ru1—C3—C8127.6 (3)C19—C20—H20119.00
C2—C3—C4107.0 (3)C21—C20—H20120.00
C2—C3—C8126.1 (4)C22—C21—H21121.00
C4—C3—C8126.6 (3)C20—C21—H21121.00
Ru1—C4—C571.39 (15)C21—C22—H22119.00
C3—C4—C9126.2 (3)C23—C22—H22120.00
Ru1—C4—C9126.8 (2)C18—C23—H23118.00
C3—C4—C5107.7 (2)C22—C23—H23118.00
Ru1—C4—C370.57 (15)C26—C25—H25119.00
C5—C4—C9125.9 (3)C24—C25—H25118.00
C1—C5—C4108.9 (2)C25—C26—H26120.00
C1—C5—C10125.5 (3)C27—C26—H26119.00
Ru1—C5—C10127.6 (2)C26—C27—H27121.00
Ru1—C5—C171.19 (17)C28—C27—H27121.00
Ru1—C5—C470.96 (15)C29—C28—H28120.00
C4—C5—C10125.5 (2)C27—C28—H28120.00
Ru1—C11—S1126.90 (13)C24—C29—H29118.00
Ru1—C11—C1272.16 (14)C28—C29—H29118.00
C12—C11—C16120.7 (2)C30—C31—H31119.00
Ru1—C11—C1671.86 (13)C32—C31—H31118.00
S1—C11—C12120.63 (18)C33—C32—H32121.00
S1—C11—C16118.70 (18)C31—C32—H32119.00
Ru1—C12—C1170.73 (14)C32—C33—H33120.00
Ru1—C12—C1371.93 (14)C34—C33—H33121.00
C11—C12—C13119.5 (2)C35—C34—H34119.00
C12—C13—C14121.1 (2)C33—C34—H34120.00
Ru1—C13—C1270.92 (14)C30—C35—H35119.00
Ru1—C13—C1472.17 (14)C34—C35—H35118.00
Ru1—C14—C1570.68 (14)C36—C37—H37118.00
C13—C14—C17120.7 (2)C38—C37—H37119.00
Ru1—C14—C17129.90 (19)C39—C38—H38120.00
C13—C14—C15118.6 (2)C37—C38—H38120.00
Ru1—C14—C1370.99 (14)C38—C39—H39119.00
C15—C14—C17120.7 (2)C40—C39—H39122.00
C14—C15—C16121.1 (2)C39—C40—H40120.00
Ru1—C15—C1472.27 (14)C41—C40—H40120.00
Ru1—C15—C1671.14 (13)C40—C41—H41119.00
Ru1—C16—C1170.49 (13)C36—C41—H41118.00
Ru1—C16—C1571.78 (13)C18—B1—C30111.52 (19)
C11—C16—C15119.1 (2)C18—B1—C36110.98 (19)
C1—C6—H6A109.00C24—B1—C36107.95 (19)
C1—C6—H6B109.00C30—B1—C36108.07 (19)
C1—C6—H6C109.00C24—B1—C30113.65 (19)
H6A—C6—H6B110.00C18—B1—C24104.62 (18)
C2—Ru1—C1—C5118.0 (3)C3—Ru1—C14—C15−121.77 (16)
C2—Ru1—C1—C6−121.2 (4)C3—Ru1—C14—C17−7.5 (3)
C3—Ru1—C1—C2−38.2 (2)C4—Ru1—C14—C13146.76 (15)
C3—Ru1—C1—C579.79 (18)C4—Ru1—C14—C15−82.09 (16)
C3—Ru1—C1—C6−159.4 (4)C4—Ru1—C14—C1732.2 (3)
C4—Ru1—C1—C2−81.1 (2)C5—Ru1—C14—C13171.82 (18)
C4—Ru1—C1—C536.95 (15)C5—Ru1—C14—C15−57.0 (2)
C4—Ru1—C1—C6157.8 (4)C5—Ru1—C14—C1757.3 (3)
C5—Ru1—C1—C2−118.0 (3)C11—Ru1—C14—C13−65.24 (15)
C5—Ru1—C1—C6120.8 (4)C11—Ru1—C14—C1565.90 (15)
C11—Ru1—C1—C2135.1 (2)C11—Ru1—C14—C17−179.8 (3)
C11—Ru1—C1—C5−106.96 (16)C12—Ru1—C14—C13−28.54 (15)
C11—Ru1—C1—C613.9 (3)C12—Ru1—C14—C15102.61 (16)
C12—Ru1—C1—C295.3 (2)C12—Ru1—C14—C17−143.1 (3)
C12—Ru1—C1—C5−146.67 (15)C13—Ru1—C14—C15131.2 (2)
C12—Ru1—C1—C6−25.8 (4)C13—Ru1—C14—C17−114.6 (3)
C13—Ru1—C1—C258.9 (2)C15—Ru1—C14—C13−131.2 (2)
C13—Ru1—C1—C5176.87 (15)C15—Ru1—C14—C17114.3 (3)
C13—Ru1—C1—C6−62.3 (4)C16—Ru1—C14—C13−102.56 (16)
C15—Ru1—C1—C2−148.0 (3)C16—Ru1—C14—C1528.59 (14)
C15—Ru1—C1—C5−30.0 (3)C16—Ru1—C14—C17142.9 (3)
C15—Ru1—C1—C690.9 (4)C1—Ru1—C15—C14170.8 (2)
C16—Ru1—C1—C2173.34 (19)C1—Ru1—C15—C16−56.2 (3)
C16—Ru1—C1—C5−68.67 (18)C2—Ru1—C15—C1454.7 (4)
C16—Ru1—C1—C652.2 (4)C2—Ru1—C15—C16−172.3 (3)
C1—Ru1—C2—C3−117.4 (3)C3—Ru1—C15—C1473.96 (18)
C1—Ru1—C2—C7122.1 (5)C3—Ru1—C15—C16−153.02 (15)
C3—Ru1—C2—C1117.4 (3)C4—Ru1—C15—C14112.18 (15)
C3—Ru1—C2—C7−120.6 (4)C4—Ru1—C15—C16−114.81 (15)
C4—Ru1—C2—C179.4 (2)C5—Ru1—C15—C14150.01 (15)
C4—Ru1—C2—C3−38.03 (18)C5—Ru1—C15—C16−76.98 (17)
C4—Ru1—C2—C7−158.6 (4)C11—Ru1—C15—C14−103.12 (16)
C5—Ru1—C2—C136.99 (18)C11—Ru1—C15—C1629.90 (14)
C5—Ru1—C2—C3−80.38 (19)C12—Ru1—C15—C14−66.26 (15)
C5—Ru1—C2—C7159.0 (4)C12—Ru1—C15—C1666.76 (15)
C11—Ru1—C2—C1−63.9 (2)C13—Ru1—C15—C14−29.53 (15)
C11—Ru1—C2—C3178.74 (16)C13—Ru1—C15—C16103.48 (16)
C11—Ru1—C2—C758.2 (4)C14—Ru1—C15—C16133.0 (2)
C12—Ru1—C2—C1−100.4 (2)C16—Ru1—C15—C14−133.0 (2)
C12—Ru1—C2—C3142.25 (17)C1—Ru1—C16—C11−73.15 (18)
C12—Ru1—C2—C721.7 (4)C1—Ru1—C16—C15155.60 (16)
C13—Ru1—C2—C1−140.12 (18)C3—Ru1—C16—C11−175.3 (2)
C13—Ru1—C2—C3102.50 (19)C3—Ru1—C16—C1553.5 (3)
C13—Ru1—C2—C7−18.1 (4)C4—Ru1—C16—C11−148.87 (14)
C14—Ru1—C2—C1−177.17 (17)C4—Ru1—C16—C1579.88 (16)
C14—Ru1—C2—C365.5 (2)C5—Ru1—C16—C11−109.44 (15)
C14—Ru1—C2—C7−55.1 (4)C5—Ru1—C16—C15119.31 (15)
C15—Ru1—C2—C1144.1 (3)C11—Ru1—C16—C15−131.3 (2)
C15—Ru1—C2—C326.7 (4)C12—Ru1—C16—C1129.07 (14)
C15—Ru1—C2—C7−93.9 (5)C12—Ru1—C16—C15−102.18 (16)
C1—Ru1—C3—C237.2 (2)C13—Ru1—C16—C1166.08 (15)
C1—Ru1—C3—C4−79.31 (19)C13—Ru1—C16—C15−65.17 (15)
C1—Ru1—C3—C8158.4 (4)C14—Ru1—C16—C11102.69 (15)
C2—Ru1—C3—C4−116.5 (3)C14—Ru1—C16—C15−28.57 (14)
C2—Ru1—C3—C8121.2 (4)C15—Ru1—C16—C11131.3 (2)
C4—Ru1—C3—C2116.5 (3)O1—S1—C11—Ru1−73.93 (18)
C4—Ru1—C3—C8−122.3 (4)O1—S1—C11—C1216.0 (2)
C5—Ru1—C3—C279.1 (2)O1—S1—C11—C16−162.05 (19)
C5—Ru1—C3—C4−37.40 (16)O2—S1—C11—Ru156.45 (18)
C5—Ru1—C3—C8−159.7 (4)O2—S1—C11—C12146.4 (2)
C12—Ru1—C3—C2−58.3 (3)O2—S1—C11—C16−31.7 (2)
C12—Ru1—C3—C4−174.81 (14)N1—S1—C11—Ru1171.02 (15)
C12—Ru1—C3—C862.9 (4)N1—S1—C11—C12−99.0 (2)
C13—Ru1—C3—C2−93.3 (2)N1—S1—C11—C1682.9 (2)
C13—Ru1—C3—C4150.16 (16)Ru1—C1—C2—C361.9 (2)
C13—Ru1—C3—C827.8 (4)Ru1—C1—C2—C7−122.3 (4)
C14—Ru1—C3—C2−131.91 (19)C5—C1—C2—Ru1−61.9 (2)
C14—Ru1—C3—C4111.59 (17)C5—C1—C2—C30.0 (4)
C14—Ru1—C3—C8−10.7 (4)C5—C1—C2—C7175.9 (4)
C15—Ru1—C3—C2−169.01 (18)C6—C1—C2—Ru1122.0 (3)
C15—Ru1—C3—C474.49 (19)C6—C1—C2—C3−176.2 (3)
C15—Ru1—C3—C8−47.8 (4)C6—C1—C2—C7−0.3 (6)
C16—Ru1—C3—C2156.2 (2)Ru1—C1—C5—C4−61.27 (19)
C16—Ru1—C3—C439.7 (3)Ru1—C1—C5—C10123.3 (3)
C16—Ru1—C3—C8−82.6 (4)C2—C1—C5—Ru161.4 (2)
C1—Ru1—C4—C380.8 (2)C2—C1—C5—C40.1 (3)
C1—Ru1—C4—C5−36.63 (16)C2—C1—C5—C10−175.3 (3)
C1—Ru1—C4—C9−158.0 (3)C6—C1—C5—Ru1−122.5 (3)
C2—Ru1—C4—C338.5 (2)C6—C1—C5—C4176.3 (3)
C2—Ru1—C4—C5−78.85 (18)C6—C1—C5—C100.8 (5)
C2—Ru1—C4—C9159.8 (3)Ru1—C2—C3—C462.4 (2)
C3—Ru1—C4—C5−117.4 (2)Ru1—C2—C3—C8−122.9 (4)
C3—Ru1—C4—C9121.2 (3)C1—C2—C3—Ru1−62.5 (2)
C5—Ru1—C4—C3117.4 (2)C1—C2—C3—C4−0.1 (4)
C5—Ru1—C4—C9−121.4 (3)C1—C2—C3—C8174.6 (4)
C11—Ru1—C4—C3165.74 (19)C7—C2—C3—Ru1121.6 (4)
C11—Ru1—C4—C548.4 (2)C7—C2—C3—C4−176.0 (4)
C11—Ru1—C4—C9−73.0 (3)C7—C2—C3—C8−1.3 (6)
C13—Ru1—C4—C3−49.9 (2)Ru1—C3—C4—C562.08 (19)
C13—Ru1—C4—C5−167.30 (16)Ru1—C3—C4—C9−121.9 (3)
C13—Ru1—C4—C971.3 (3)C2—C3—C4—Ru1−62.0 (2)
C14—Ru1—C4—C3−83.29 (19)C2—C3—C4—C50.1 (3)
C14—Ru1—C4—C5159.34 (14)C2—C3—C4—C9176.1 (3)
C14—Ru1—C4—C937.9 (3)C8—C3—C4—Ru1123.4 (4)
C15—Ru1—C4—C3−121.66 (18)C8—C3—C4—C5−174.5 (4)
C15—Ru1—C4—C5120.96 (15)C8—C3—C4—C91.5 (6)
C15—Ru1—C4—C9−0.4 (3)Ru1—C4—C5—C161.41 (19)
C16—Ru1—C4—C3−159.79 (18)Ru1—C4—C5—C10−123.2 (3)
C16—Ru1—C4—C582.84 (16)C3—C4—C5—Ru1−61.6 (2)
C16—Ru1—C4—C9−38.6 (3)C3—C4—C5—C1−0.1 (3)
C1—Ru1—C5—C4118.6 (2)C3—C4—C5—C10175.3 (3)
C1—Ru1—C5—C10−120.7 (3)C9—C4—C5—Ru1122.4 (3)
C2—Ru1—C5—C1−37.25 (18)C9—C4—C5—C1−176.2 (3)
C2—Ru1—C5—C481.38 (19)C9—C4—C5—C10−0.7 (5)
C2—Ru1—C5—C10−158.0 (3)Ru1—C11—C12—C13−54.9 (2)
C3—Ru1—C5—C1−80.79 (19)S1—C11—C12—Ru1−122.85 (18)
C3—Ru1—C5—C437.85 (17)S1—C11—C12—C13−177.76 (19)
C3—Ru1—C5—C10158.5 (3)C16—C11—C12—Ru155.2 (2)
C4—Ru1—C5—C1−118.6 (2)C16—C11—C12—C130.3 (4)
C4—Ru1—C5—C10120.6 (3)Ru1—C11—C16—C1554.8 (2)
C11—Ru1—C5—C188.88 (17)S1—C11—C16—Ru1122.75 (17)
C11—Ru1—C5—C4−152.49 (14)S1—C11—C16—C15177.54 (18)
C11—Ru1—C5—C10−31.9 (3)C12—C11—C16—Ru1−55.3 (2)
C12—Ru1—C5—C153.3 (2)C12—C11—C16—C15−0.5 (3)
C12—Ru1—C5—C4171.90 (15)Ru1—C12—C13—C14−54.1 (2)
C12—Ru1—C5—C10−67.5 (3)C11—C12—C13—Ru154.3 (2)
C14—Ru1—C5—C1−157.18 (18)C11—C12—C13—C140.3 (4)
C14—Ru1—C5—C4−38.6 (3)Ru1—C13—C14—C15−54.1 (2)
C14—Ru1—C5—C1082.1 (3)Ru1—C13—C14—C17125.8 (2)
C15—Ru1—C5—C1166.53 (15)C12—C13—C14—Ru153.5 (2)
C15—Ru1—C5—C4−74.84 (17)C12—C13—C14—C15−0.6 (4)
C15—Ru1—C5—C1045.8 (3)C12—C13—C14—C17179.3 (2)
C16—Ru1—C5—C1128.54 (16)Ru1—C14—C15—C16−53.9 (2)
C16—Ru1—C5—C4−112.83 (15)C13—C14—C15—Ru154.2 (2)
C16—Ru1—C5—C107.8 (3)C13—C14—C15—C160.3 (4)
C1—Ru1—C11—S112.9 (2)C17—C14—C15—Ru1−125.6 (2)
C1—Ru1—C11—C12−102.41 (17)C17—C14—C15—C16−179.5 (2)
C1—Ru1—C11—C16125.61 (16)Ru1—C15—C16—C11−54.2 (2)
C2—Ru1—C11—S148.4 (2)C14—C15—C16—Ru154.4 (2)
C2—Ru1—C11—C12−66.9 (2)C14—C15—C16—C110.2 (4)
C2—Ru1—C11—C16161.09 (17)C23—C18—C19—C20−1.2 (4)
C4—Ru1—C11—S1−57.5 (2)B1—C18—C19—C20174.8 (2)
C4—Ru1—C11—C12−172.78 (16)C19—C18—C23—C220.6 (4)
C4—Ru1—C11—C1655.2 (2)B1—C18—C23—C22−175.5 (2)
C5—Ru1—C11—S1−27.07 (19)C19—C18—B1—C24−112.9 (3)
C5—Ru1—C11—C12−142.39 (14)C19—C18—B1—C3010.3 (3)
C5—Ru1—C11—C1685.63 (15)C19—C18—B1—C36130.9 (2)
C12—Ru1—C11—S1115.3 (2)C23—C18—B1—C2462.8 (3)
C12—Ru1—C11—C16−132.0 (2)C23—C18—B1—C30−174.0 (2)
C13—Ru1—C11—S1144.83 (18)C23—C18—B1—C36−53.4 (3)
C13—Ru1—C11—C1229.51 (14)C18—C19—C20—C210.6 (4)
C13—Ru1—C11—C16−102.47 (15)C19—C20—C21—C220.5 (4)
C14—Ru1—C11—S1−178.83 (17)C20—C21—C22—C23−1.1 (4)
C14—Ru1—C11—C1265.85 (15)C21—C22—C23—C180.5 (4)
C14—Ru1—C11—C16−66.13 (14)C29—C24—C25—C263.2 (4)
C15—Ru1—C11—S1−142.17 (18)B1—C24—C25—C26−170.1 (2)
C15—Ru1—C11—C12102.51 (15)C25—C24—C29—C28−3.1 (4)
C15—Ru1—C11—C16−29.47 (14)B1—C24—C29—C28170.5 (2)
C16—Ru1—C11—S1−112.7 (2)C25—C24—B1—C1891.4 (3)
C16—Ru1—C11—C12132.0 (2)C25—C24—B1—C30−30.5 (3)
C1—Ru1—C12—C1192.39 (16)C25—C24—B1—C36−150.4 (2)
C1—Ru1—C12—C13−136.15 (16)C29—C24—B1—C18−81.5 (3)
C2—Ru1—C12—C11132.98 (16)C29—C24—B1—C30156.6 (2)
C2—Ru1—C12—C13−95.57 (17)C29—C24—B1—C3636.7 (3)
C3—Ru1—C12—C11167.65 (18)C24—C25—C26—C27−0.9 (4)
C3—Ru1—C12—C13−60.9 (2)C25—C26—C27—C28−1.7 (4)
C5—Ru1—C12—C1160.6 (2)C26—C27—C28—C291.9 (4)
C5—Ru1—C12—C13−167.95 (15)C27—C28—C29—C240.7 (4)
C11—Ru1—C12—C13131.5 (2)C35—C30—C31—C322.2 (4)
C13—Ru1—C12—C11−131.5 (2)B1—C30—C31—C32−177.0 (3)
C14—Ru1—C12—C11−103.14 (16)C31—C30—C35—C34−2.4 (4)
C14—Ru1—C12—C1328.31 (14)B1—C30—C35—C34176.9 (3)
C15—Ru1—C12—C11−66.35 (15)C31—C30—B1—C18−62.2 (3)
C15—Ru1—C12—C1365.10 (15)C31—C30—B1—C2455.8 (3)
C16—Ru1—C12—C11−29.47 (14)C31—C30—B1—C36175.6 (2)
C16—Ru1—C12—C13101.99 (16)C35—C30—B1—C18118.7 (3)
C1—Ru1—C13—C1265.1 (2)C35—C30—B1—C24−123.4 (3)
C1—Ru1—C13—C14−161.64 (15)C35—C30—B1—C36−3.6 (3)
C2—Ru1—C13—C1298.85 (18)C30—C31—C32—C33−0.5 (5)
C2—Ru1—C13—C14−127.90 (17)C31—C32—C33—C34−1.2 (6)
C3—Ru1—C13—C12140.35 (16)C32—C33—C34—C351.0 (6)
C3—Ru1—C13—C14−86.41 (18)C33—C34—C35—C300.9 (6)
C4—Ru1—C13—C12171.26 (15)C41—C36—C37—C380.4 (4)
C4—Ru1—C13—C14−55.5 (2)B1—C36—C37—C38−174.9 (3)
C11—Ru1—C13—C12−29.47 (14)C37—C36—C41—C40−1.1 (4)
C11—Ru1—C13—C14103.77 (16)B1—C36—C41—C40174.4 (3)
C12—Ru1—C13—C14133.3 (2)C37—C36—B1—C18−15.6 (3)
C14—Ru1—C13—C12−133.3 (2)C37—C36—B1—C24−129.7 (2)
C15—Ru1—C13—C12−103.56 (16)C37—C36—B1—C30107.0 (3)
C15—Ru1—C13—C1429.69 (15)C41—C36—B1—C18169.4 (2)
C16—Ru1—C13—C12−66.88 (15)C41—C36—B1—C2455.2 (3)
C16—Ru1—C13—C1466.36 (15)C41—C36—B1—C30−68.1 (3)
C2—Ru1—C14—C1370.8 (2)C36—C37—C38—C391.0 (5)
C2—Ru1—C14—C15−158.02 (17)C37—C38—C39—C40−1.6 (5)
C2—Ru1—C14—C17−43.7 (3)C38—C39—C40—C410.9 (5)
C3—Ru1—C14—C13107.08 (17)C39—C40—C41—C360.5 (5)
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x+1, −y, −z; (v) −x+3/2, y+1/2, −z+1/2; (vi) −x+1, −y+1, −z; (vii) −x+2, −y, −z.
Acknowledgements top

The authors acknowledge support of this work by Griffith University, the Queensland University of Technology and the Eskitis Institute for Cell and Molecular Therapies.

references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

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

Ferguson, G. & Glidewell, C. (1988). J. Chem. Soc. Perkin Trans. 2, pp. 2129–2132.

Gemel, C., Mereiter, K., Schmid, R. & Kirchner, K. (1996). Organometallics, 15, 532–542.

Loughrey, B. T., Healy, P. C., Parsons, P. G. & Williams, M. L. (2008). Inorg. Chem. 47, 8589–8591.

Moreno, A., Pregosin, P. S., Veiros, L. F., Albinati, A. & Rizzato, S. (2008). Chem. Eur. J. 14, 5617–5629.

Navarro Clemente, M. E., Juárez Saavedra, P., Cervantes Vásquez, M., Paz-Sandoval, M. A., Arif, A. M. & Ernst, R. D. (2002). Organometallics, 21, 592–605.

Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.

Salmon, A. J., Williams, M. L., Innocenti, A., Vullo, D., Supuran, C. T. & Poulsen, S.-A. (2007). Bioorg. Med. Chem. Lett. 17, 5032–5035.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Zerbe, E.-M., Moers, O., Jones, P. G. & Blaschette, A. (2005). Z. Naturforsch. 60b, 125–138.