Acta Cryst. (2009). E65, m1371-m1372 [ doi:10.1107/S1600536809041324 ]
Reaction of dichloridotetrakis(dimethyl sulfoxide)ruthenium(II) and N-[3,5-di-tert-butyl-2-(trimethylsilyloxy)benzyl]-N,N-bis(2-pyridylmethyl)amine (BPPA-TMS) affords the thermodynamic product cis,fac-[RuCl2(BPPA-TMS)(DMSO)] and kinetic product trans,mer-[RuCl2(BPPA-TMS)(DMSO)]. The title complex, [RuCl2(C30H43N3OSi)(C2H6OS)]·2CH2Cl2, crystallizes as a dichloromethane disolvate, with two formula units in the asymmetric unit. The complex exhibits a distorted-octahedral geometry about the low spin d6 RuII center. The BPPA-TMS ligand is coordinated in a facial fashion, with the DMSO ligand cis to the aliphatic nitrogen atom of the BPPA-TMS ligand. One of the two dichloromethane solvate molecules is disordered over two positions in a 0.695:0.305 ratio.
The following procedures were conducted under nitrogen using standard techniques for handling air and moisture sensitive substances. Ethanol (40 ml) was added to BPPA-TMS (1.50 g, 3.06 mmol) and RuCl2(DMSO)4 (1.48 g, 3.06 mmol). The mixture was heated to reflux (15 hr); the solids dissolved affording a red-orange solution. Solvent removal in vacuo provided a red oily residue that was washed with pentane (10 ml). Treatment with Et2O (45 ml) resulted in a yellow solid containing 1 and 2. The suspension was vigorously stirred (20 min) to generate a fine powder. The Et2O was decanted, and the solid was dried in vacuo. Kinetic product 2 was extracted with toluene (30 ml); the remaining solid was washed with toluene (10 ml) to remove traces of 2. The residue was dried in vacuo, and 1 was extracted with CH2Cl2 (30 ml). The CH2Cl2 extract was filtered, and the solvent removed in vacuo revealing yellow-orange 1. Pentane diffusion into a dichloromethane solution of 1 yielded crystals of 1 with 2 CH2Cl2 molecules per formula unit (1.13 g, 40%). Mp: 162–163 °C (dec).
All hydrogen atoms were placed in ideal positions with C-H ranging from 0.95Å to 0.99Å and U(H) set to 1.2Ueq(C) or 1.5Ueq(Cmethyl) and refined as riding atoms. Two dichloromethane molecules were multipositioned. These could not be modeled as anisotropic, partial molecules and their contribution to the scattering power was suppressed using the SQUEEZE option in PLATON (Spek, 2003). One of the two remaining dichloromethane solvents refined well while the other was split into two fragments refining to a 0.693 (16):0.307 (16) ratio. The final refinement employed 24 bond distance (SAME) and anisotropic (DELU) restraints.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
![[Figure 1]](./bt5088fig1thm.gif)
| Fig. 1. Molecular structure of one of the two molecules in the asymmetric unit of 1 (50% displacement ellipsoids). The solvent molecules are not shown. |
| [RuCl2(C30H43N3OSi)(C2H6OS)]·2CH2Cl2 | Z = 4 |
| Mr = 909.71 | F(000) = 1880 |
| Triclinic, P1 | Dx = 1.393 Mg m−3 |
| Hall symbol: -P 1 | Melting point: 162 K |
| a = 10.913 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 18.435 (4) Å | Cell parameters from 7479 reflections |
| c = 22.413 (5) Å | θ = 2.5–23.0° |
| α = 82.039 (3)° | µ = 0.84 mm−1 |
| β = 76.212 (3)° | T = 126 K |
| γ = 89.148 (3)° | Plate, yellow |
| V = 4336.4 (15) Å3 | 0.33 × 0.31 × 0.02 mm |
| Bruker SMART CCD area-detector diffractometer | 15775 independent reflections |
| Radiation source: sealed tube | 8958 reflections with I > 2σ(I) |
| graphite | Rint = 0.085 |
| φ and ω scans | θmax = 25.4°, θmin = 2.5° |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −12→13 |
| Tmin = 0.769, Tmax = 0.988 | k = −21→22 |
| 52307 measured reflections | l = 0→26 |
| 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.124 | H-atom parameters constrained |
| S = 0.98 | w = 1/[σ2(Fo2) + (0.0583P)2] where P = (Fo2 + 2Fc2)/3 |
| 15775 reflections | (Δ/σ)max = 0.001 |
| 861 parameters | Δρmax = 0.70 e Å−3 |
| 24 restraints | Δρmin = −0.57 e Å−3 |
| [RuCl2(C30H43N3OSi)(C2H6OS)]·2CH2Cl2 | γ = 89.148 (3)° |
| Mr = 909.71 | V = 4336.4 (15) Å3 |
| Triclinic, P1 | Z = 4 |
| a = 10.913 (2) Å | Mo Kα radiation |
| b = 18.435 (4) Å | µ = 0.84 mm−1 |
| c = 22.413 (5) Å | T = 126 K |
| α = 82.039 (3)° | 0.33 × 0.31 × 0.02 mm |
| β = 76.212 (3)° |
| Bruker SMART CCD area-detector diffractometer | 15775 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 8958 reflections with I > 2σ(I) |
| Tmin = 0.769, Tmax = 0.988 | Rint = 0.085 |
| 52307 measured reflections | θmax = 25.4° |
| R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
| wR(F2) = 0.124 | Δρmax = 0.70 e Å−3 |
| S = 0.98 | Δρmin = −0.57 e Å−3 |
| 15775 reflections | Absolute structure: ? |
| 861 parameters | Flack parameter: ? |
| 24 restraints | Rogers parameter: ? |
Experimental. Anal Calcd. For C34H53Cl6N3O2SSiRu C, 44.89; H, 5.87; N, 4.62. Found C, 45.13; H, 5.86; N, 4.96. NMR (CD3CN, 400 MHz) 1H δ 9.73 (d, J = 5.2 Hz 1H, α-pyridyl), 9.27 (d, J = 5.2, 1H, α-pyridyl), 7.57 (app t, J = 7.6 Hz, 1H, para-pyridyl), 7.44 (app t, J = 7.6 Hz, 1H, para-pyridyl), 7.37 (d, J = 2.4, 1H, aromatic phenol), 7.24 (app t, J = 6.0 Hz, 1H, B-pyridyl), 7.18 (d, J = 2.4 Hz, 1H, aromatic phenol), 7.01 (app t, J = 6.4 Hz, 1H, B-pyridyl), 6.94 (m, 2H, pyridyl), 5.27 (s, 4H, CH2Cl2), 5.05 (d, J = 14 Hz, 1H, NCH2py), 4.95 (d, J = 15 Hz, 1H, NCH2py), 4.69 (d, J = 14 Hz, 1H, NCH2py), 4.56 (d, J = 16 Hz, 1H, NCH2py), 3.62 (s, 3H, DMSO), 3.28 (d, J = 15 Hz, 1H, NCH2Ph), 3.11 (d, J = 17 Hz, NCH2Ph), 2.87 (s, 3H, DMSO), 1.41 (sm, 9H, tert-Bu), 1.29 (s, 9H, tert-Bu), 0.156 (s, 9H, SiMe3). NMR (CD3CN, 400 MHz) 13C{1H} δ 164.3, 160.9, 154.5, 153.2, 151.6, 143.0, 140.6, 136.5, 135.0, 129.3, 125.5, 123.7, 123.6, 123.5, 120.6, 119.6, 68.7, 65.1, 63.8, 53.6, 44.8, 44.0, 35.4, 34.2, 31.6, 31.4, 2.1. The expected sixteen aromatic carbon environments are present, along with eleven other environments (including one for for dichloromethane solvate), consistent with the solid-state structure of 1. |
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. A crystal (approximate dimensions 1/4x 0.12 x 0.04 mm3) was placed onto the tip of a 0.1 mm diameter glass capillary and mounted on a CCD area detector diffractometer for a data collection at 173 (2) K (SMART V5.054, Bruker Analytical X-ray Systems, Madison, WI (2001).). A preliminary set of cell constants was calculated from reflections harvested from three sets of 20 frames. These initial sets of frames were oriented such that orthogonal wedges of reciprocal space were surveyed. This produced initial orientation matrices determined from 48 reflections. The data collection was carried out using Mo Kα radiation (graphite monochromator) with a frame time of 8 s and a detector distance of 4.8 cm. A randomly oriented region of reciprocal space was surveyed to the extent of one sphere and to a resolution of 0.77 Å. Four major sections of frames were collected with 0.30° steps in ω at four different φ settings and a detector position of -28° in 2θ. The intensity data were corrected for absorption and decay (SADABS). 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. The structure is P-1 with two complexes and four dichloromethane molecules per asymmetric unit. The two indpendent ruthenium complexes are enantiomeric. The structure is best described as having Z=4 and Z'=2. The two ruthenium complexes are related by a pseudo-b-glide perpendicular to the a axis. The fit is quite good for the atoms bound to the Ru atom, but the atoms on the benzyl portion are not as good. However, this is just pseudosymmetry. The four dichlormethane molecules are related similarly. Two dichloromethane molecules were multipositioned. These could not be modeled as anisotropic, partial molecules. These two were commented out of the res file and PLATON/Squeeze was run to remove diffuse scattering effects from the diffraction data. PLATON / Squeeze results (Spek, 2009): Total Potential Solvent Area Vol: 608.2 Å per Unit Cell Vol: 4336.4 Å [14.0%] Total Potential Solvent Accessible Void Vol: 608.2 Å Electron Count / Cell = 67 - To be included in D(calc), F000 & Mol.Wght. Correction - Since two DCM with electron count = 84 were removed, then 84 electron will be added into F000. The empirical formula is correct. One of the two remaining dichloromethane solvents refined well while the other was split into two fragments refining to a 0.695:0.305 ratio. The final refinement employed 24 bond distance (SAME) and anisotropic (DELU) restraints. |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Ru1A | 0.29376 (4) | 0.13565 (2) | 0.115631 (17) | 0.01704 (11) | |
| Cl1A | 0.30575 (12) | 0.24252 (6) | 0.16712 (5) | 0.0241 (3) | |
| Cl2A | 0.34173 (12) | 0.21477 (7) | 0.01658 (5) | 0.0265 (3) | |
| S1A | 0.08900 (11) | 0.15552 (7) | 0.12116 (6) | 0.0208 (3) | |
| Si1A | 0.49345 (14) | 0.11139 (8) | 0.33698 (7) | 0.0304 (4) | |
| O1A | 0.4449 (3) | 0.03571 (17) | 0.31556 (14) | 0.0276 (9) | |
| O2A | −0.0055 (3) | 0.12446 (18) | 0.17877 (14) | 0.0271 (9) | |
| N1A | 0.2767 (4) | 0.04179 (19) | 0.07772 (17) | 0.0190 (9) | |
| N2A | 0.4846 (3) | 0.1227 (2) | 0.11801 (16) | 0.0182 (9) | |
| N3A | 0.2778 (4) | 0.0513 (2) | 0.19379 (17) | 0.0179 (9) | |
| C1A | 0.3088 (5) | 0.0334 (3) | 0.0179 (2) | 0.0254 (12) | |
| H1AA | 0.3552 | 0.0716 | −0.0112 | 0.031* | |
| C2A | 0.2771 (5) | −0.0283 (3) | −0.0033 (2) | 0.0342 (14) | |
| H2AB | 0.3019 | −0.0321 | −0.0463 | 0.041* | |
| C3A | 0.2101 (5) | −0.0843 (3) | 0.0369 (3) | 0.0353 (14) | |
| H3AA | 0.1853 | −0.1263 | 0.0222 | 0.042* | |
| C4A | 0.1794 (5) | −0.0784 (3) | 0.0994 (2) | 0.0302 (13) | |
| H4AA | 0.1357 | −0.1174 | 0.1286 | 0.036* | |
| C5A | 0.2133 (4) | −0.0146 (3) | 0.1192 (2) | 0.0227 (12) | |
| C6A | 0.1828 (5) | −0.0024 (3) | 0.1866 (2) | 0.0236 (12) | |
| H6AA | 0.0967 | 0.0169 | 0.1986 | 0.028* | |
| H6AB | 0.1869 | −0.0493 | 0.2136 | 0.028* | |
| C7A | 0.4031 (4) | 0.0129 (2) | 0.1856 (2) | 0.0188 (11) | |
| H7AA | 0.4122 | −0.0126 | 0.2262 | 0.023* | |
| H7AB | 0.4065 | −0.0241 | 0.1573 | 0.023* | |
| C8A | 0.5079 (5) | 0.0677 (2) | 0.1596 (2) | 0.0198 (11) | |
| C9A | 0.6227 (5) | 0.0616 (3) | 0.1757 (2) | 0.0240 (12) | |
| H9AA | 0.6372 | 0.0219 | 0.2049 | 0.029* | |
| C10A | 0.7160 (5) | 0.1139 (3) | 0.1486 (2) | 0.0292 (13) | |
| H10A | 0.7957 | 0.1106 | 0.1589 | 0.035* | |
| C11A | 0.6914 (4) | 0.1714 (3) | 0.1061 (2) | 0.0252 (13) | |
| H11B | 0.7538 | 0.2083 | 0.0872 | 0.030* | |
| C12A | 0.5754 (4) | 0.1742 (3) | 0.0919 (2) | 0.0238 (12) | |
| H12B | 0.5587 | 0.2134 | 0.0629 | 0.029* | |
| C13A | 0.2423 (4) | 0.0793 (2) | 0.2559 (2) | 0.0198 (11) | |
| H13A | 0.1617 | 0.1056 | 0.2589 | 0.024* | |
| H13B | 0.3077 | 0.1153 | 0.2572 | 0.024* | |
| C14A | 0.2280 (5) | 0.0210 (3) | 0.3121 (2) | 0.0235 (12) | |
| C15A | 0.3303 (4) | −0.0031 (3) | 0.3377 (2) | 0.0198 (11) | |
| C16A | 0.3174 (5) | −0.0649 (3) | 0.3827 (2) | 0.0223 (12) | |
| C17A | 0.1948 (5) | −0.0944 (3) | 0.4064 (2) | 0.0277 (13) | |
| H17A | 0.1837 | −0.1358 | 0.4377 | 0.033* | |
| C18A | 0.0890 (5) | −0.0676 (3) | 0.3876 (2) | 0.0265 (13) | |
| C19A | 0.1088 (5) | −0.0115 (3) | 0.3380 (2) | 0.0233 (12) | |
| H19A | 0.0397 | 0.0053 | 0.3213 | 0.028* | |
| C20A | −0.0437 (5) | −0.0989 (3) | 0.4162 (3) | 0.0395 (15) | |
| C21A | −0.1305 (6) | −0.0365 (4) | 0.4392 (3) | 0.073 (2) | |
| H21A | −0.2174 | −0.0553 | 0.4547 | 0.109* | |
| H21B | −0.1268 | 0.0031 | 0.4048 | 0.109* | |
| H21C | −0.1022 | −0.0177 | 0.4726 | 0.109* | |
| C22A | −0.0947 (6) | −0.1316 (4) | 0.3685 (3) | 0.079 (3) | |
| H22A | −0.0355 | −0.1676 | 0.3504 | 0.119* | |
| H22B | −0.1053 | −0.0927 | 0.3357 | 0.119* | |
| H22C | −0.1765 | −0.1557 | 0.3885 | 0.119* | |
| C23A | −0.0488 (5) | −0.1573 (3) | 0.4723 (3) | 0.0505 (18) | |
| H23A | −0.0014 | −0.2001 | 0.4588 | 0.076* | |
| H23B | −0.1368 | −0.1719 | 0.4917 | 0.076* | |
| H23C | −0.0114 | −0.1374 | 0.5024 | 0.076* | |
| C24A | 0.4293 (5) | −0.1028 (3) | 0.4046 (2) | 0.0287 (13) | |
| C25A | 0.3952 (6) | −0.1816 (3) | 0.4386 (3) | 0.0517 (18) | |
| H25A | 0.3609 | −0.2100 | 0.4123 | 0.078* | |
| H25B | 0.3321 | −0.1795 | 0.4776 | 0.078* | |
| H25C | 0.4712 | −0.2051 | 0.4476 | 0.078* | |
| C26A | 0.5413 (5) | −0.1092 (3) | 0.3498 (3) | 0.0465 (16) | |
| H26A | 0.5748 | −0.0602 | 0.3309 | 0.070* | |
| H26B | 0.5138 | −0.1337 | 0.3190 | 0.070* | |
| H26C | 0.6074 | −0.1379 | 0.3645 | 0.070* | |
| C27A | 0.4694 (5) | −0.0597 (3) | 0.4507 (2) | 0.0417 (15) | |
| H27A | 0.4961 | −0.0100 | 0.4304 | 0.063* | |
| H27B | 0.5397 | −0.0843 | 0.4648 | 0.063* | |
| H27C | 0.3981 | −0.0571 | 0.4864 | 0.063* | |
| C28A | 0.3788 (6) | 0.1316 (3) | 0.4077 (2) | 0.0467 (17) | |
| H28A | 0.2999 | 0.1481 | 0.3972 | 0.070* | |
| H28B | 0.4136 | 0.1701 | 0.4253 | 0.070* | |
| H28C | 0.3622 | 0.0872 | 0.4383 | 0.070* | |
| C29A | 0.6577 (5) | 0.0943 (3) | 0.3460 (3) | 0.0551 (19) | |
| H29A | 0.7100 | 0.0803 | 0.3075 | 0.083* | |
| H29B | 0.6563 | 0.0547 | 0.3802 | 0.083* | |
| H29C | 0.6929 | 0.1390 | 0.3550 | 0.083* | |
| C30A | 0.5066 (5) | 0.1913 (3) | 0.2768 (2) | 0.0393 (15) | |
| H30A | 0.4221 | 0.2067 | 0.2732 | 0.059* | |
| H30B | 0.5546 | 0.1783 | 0.2370 | 0.059* | |
| H30C | 0.5503 | 0.2315 | 0.2880 | 0.059* | |
| C31A | 0.0407 (5) | 0.1256 (3) | 0.0575 (2) | 0.0300 (13) | |
| H31A | −0.0439 | 0.1435 | 0.0568 | 0.045* | |
| H31B | 0.0396 | 0.0719 | 0.0623 | 0.045* | |
| H31C | 0.1002 | 0.1449 | 0.0185 | 0.045* | |
| C32A | 0.0529 (5) | 0.2500 (2) | 0.1080 (2) | 0.0284 (13) | |
| H32A | −0.0375 | 0.2550 | 0.1099 | 0.043* | |
| H32B | 0.1015 | 0.2717 | 0.0669 | 0.043* | |
| H32C | 0.0747 | 0.2754 | 0.1398 | 0.043* | |
| Ru1B | 0.09676 (4) | 0.63569 (2) | 0.115900 (18) | 0.01900 (12) | |
| Cl1B | 0.04663 (12) | 0.74054 (6) | 0.17174 (6) | 0.0278 (3) | |
| Cl2B | 0.11675 (13) | 0.71495 (7) | 0.01828 (6) | 0.0323 (3) | |
| S1B | 0.30095 (12) | 0.65563 (7) | 0.10974 (6) | 0.0247 (3) | |
| Si1B | −0.21556 (15) | 0.61342 (9) | 0.37330 (7) | 0.0355 (4) | |
| O1B | −0.1606 (3) | 0.53386 (18) | 0.34994 (15) | 0.0296 (9) | |
| O2B | 0.3538 (3) | 0.62659 (19) | 0.16344 (16) | 0.0341 (9) | |
| N1B | 0.1388 (4) | 0.5427 (2) | 0.07480 (18) | 0.0227 (10) | |
| N2B | −0.0989 (4) | 0.6230 (2) | 0.13090 (18) | 0.0219 (10) | |
| N3B | 0.0615 (3) | 0.5517 (2) | 0.19497 (17) | 0.0185 (9) | |
| C1B | 0.1459 (5) | 0.5359 (3) | 0.0146 (2) | 0.0268 (13) | |
| H1BA | 0.1197 | 0.5755 | −0.0112 | 0.032* | |
| C2B | 0.1902 (5) | 0.4731 (3) | −0.0107 (2) | 0.0334 (14) | |
| H2BB | 0.1956 | 0.4701 | −0.0532 | 0.040* | |
| C3B | 0.2263 (5) | 0.4147 (3) | 0.0269 (2) | 0.0348 (14) | |
| H3BA | 0.2582 | 0.3716 | 0.0104 | 0.042* | |
| C4B | 0.2153 (5) | 0.4203 (3) | 0.0897 (2) | 0.0277 (13) | |
| H4BA | 0.2376 | 0.3805 | 0.1166 | 0.033* | |
| C5B | 0.1715 (4) | 0.4846 (3) | 0.1120 (2) | 0.0220 (12) | |
| C6B | 0.1608 (4) | 0.4966 (2) | 0.1781 (2) | 0.0205 (11) | |
| H6BA | 0.1382 | 0.4499 | 0.2061 | 0.025* | |
| H6BB | 0.2427 | 0.5145 | 0.1827 | 0.025* | |
| C7B | −0.0641 (4) | 0.5167 (2) | 0.1998 (2) | 0.0212 (12) | |
| H7BA | −0.0519 | 0.4752 | 0.1755 | 0.025* | |
| H7BB | −0.1013 | 0.4968 | 0.2437 | 0.025* | |
| C8B | −0.1535 (5) | 0.5687 (3) | 0.1771 (2) | 0.0209 (12) | |
| C9B | −0.2821 (5) | 0.5614 (3) | 0.1982 (2) | 0.0313 (13) | |
| H9BA | −0.3181 | 0.5234 | 0.2306 | 0.038* | |
| C10B | −0.3592 (5) | 0.6103 (3) | 0.1717 (3) | 0.0367 (15) | |
| H10B | −0.4485 | 0.6055 | 0.1852 | 0.044* | |
| C11B | −0.3037 (5) | 0.6664 (3) | 0.1252 (3) | 0.0359 (14) | |
| H11A | −0.3541 | 0.7011 | 0.1069 | 0.043* | |
| C12B | −0.1740 (5) | 0.6704 (3) | 0.1064 (2) | 0.0275 (13) | |
| H12A | −0.1360 | 0.7085 | 0.0745 | 0.033* | |
| C13B | 0.0659 (5) | 0.5802 (3) | 0.25443 (19) | 0.0225 (12) | |
| H13C | 0.1443 | 0.6099 | 0.2470 | 0.027* | |
| H13D | −0.0062 | 0.6131 | 0.2650 | 0.027* | |
| C14B | 0.0617 (5) | 0.5227 (3) | 0.3090 (2) | 0.0230 (12) | |
| C15B | −0.0486 (5) | 0.4984 (3) | 0.3533 (2) | 0.0250 (12) | |
| C16B | −0.0451 (5) | 0.4371 (3) | 0.3990 (2) | 0.0276 (13) | |
| C17B | 0.0722 (5) | 0.4081 (3) | 0.4004 (2) | 0.0311 (14) | |
| H17B | 0.0757 | 0.3676 | 0.4311 | 0.037* | |
| C18B | 0.1847 (5) | 0.4341 (3) | 0.3601 (2) | 0.0294 (13) | |
| C19B | 0.1757 (5) | 0.4917 (3) | 0.3149 (2) | 0.0287 (13) | |
| H19B | 0.2510 | 0.5110 | 0.2866 | 0.034* | |
| C20B | 0.3134 (5) | 0.3992 (3) | 0.3607 (3) | 0.0381 (15) | |
| C21B | 0.3074 (7) | 0.3400 (4) | 0.4148 (3) | 0.089 (3) | |
| H21D | 0.3919 | 0.3204 | 0.4133 | 0.134* | |
| H21E | 0.2501 | 0.3005 | 0.4126 | 0.134* | |
| H21F | 0.2764 | 0.3604 | 0.4536 | 0.134* | |
| C22B | 0.3627 (8) | 0.3685 (5) | 0.3007 (3) | 0.102 (3) | |
| H22D | 0.4485 | 0.3508 | 0.2988 | 0.153* | |
| H22E | 0.3640 | 0.4070 | 0.2656 | 0.153* | |
| H22F | 0.3078 | 0.3278 | 0.2986 | 0.153* | |
| C23B | 0.4075 (6) | 0.4569 (4) | 0.3655 (3) | 0.074 (2) | |
| H23D | 0.4914 | 0.4355 | 0.3609 | 0.111* | |
| H23E | 0.3815 | 0.4740 | 0.4061 | 0.111* | |
| H23F | 0.4101 | 0.4983 | 0.3326 | 0.111* | |
| C24B | −0.1653 (5) | 0.4035 (3) | 0.4473 (2) | 0.0344 (14) | |
| C25B | −0.1391 (6) | 0.3274 (3) | 0.4791 (3) | 0.0499 (18) | |
| H25D | −0.2166 | 0.3071 | 0.5082 | 0.075* | |
| H25E | −0.0736 | 0.3318 | 0.5017 | 0.075* | |
| H25F | −0.1105 | 0.2949 | 0.4477 | 0.075* | |
| C26B | −0.2744 (6) | 0.3947 (3) | 0.4168 (3) | 0.0524 (18) | |
| H26D | −0.3490 | 0.3749 | 0.4485 | 0.079* | |
| H26E | −0.2504 | 0.3609 | 0.3860 | 0.079* | |
| H26F | −0.2939 | 0.4425 | 0.3964 | 0.079* | |
| C27B | −0.2033 (6) | 0.4525 (3) | 0.4985 (2) | 0.0491 (18) | |
| H27D | −0.2791 | 0.4319 | 0.5289 | 0.074* | |
| H27E | −0.2208 | 0.5018 | 0.4802 | 0.074* | |
| H27F | −0.1343 | 0.4552 | 0.5193 | 0.074* | |
| C28B | −0.1051 (6) | 0.6473 (3) | 0.4147 (3) | 0.0505 (17) | |
| H28D | −0.0215 | 0.6557 | 0.3864 | 0.076* | |
| H28E | −0.0994 | 0.6109 | 0.4501 | 0.076* | |
| H28F | −0.1359 | 0.6934 | 0.4295 | 0.076* | |
| C29B | −0.3792 (6) | 0.5965 (3) | 0.4213 (3) | 0.0556 (18) | |
| H29D | −0.3771 | 0.5670 | 0.4610 | 0.083* | |
| H29E | −0.4279 | 0.5701 | 0.3993 | 0.083* | |
| H29F | −0.4190 | 0.6434 | 0.4290 | 0.083* | |
| C30B | −0.2306 (6) | 0.6826 (3) | 0.3077 (3) | 0.0477 (16) | |
| H30D | −0.1471 | 0.6941 | 0.2799 | 0.072* | |
| H30E | −0.2667 | 0.7272 | 0.3234 | 0.072* | |
| H30F | −0.2860 | 0.6633 | 0.2848 | 0.072* | |
| C31B | 0.4028 (5) | 0.6244 (3) | 0.0436 (2) | 0.0397 (15) | |
| H31D | 0.4893 | 0.6417 | 0.0395 | 0.059* | |
| H31E | 0.3745 | 0.6436 | 0.0062 | 0.059* | |
| H31F | 0.4005 | 0.5707 | 0.0489 | 0.059* | |
| C32B | 0.3455 (5) | 0.7505 (3) | 0.0915 (2) | 0.0321 (14) | |
| H32D | 0.4363 | 0.7559 | 0.0879 | 0.048* | |
| H32E | 0.2988 | 0.7771 | 0.1245 | 0.048* | |
| H32F | 0.3259 | 0.7705 | 0.0520 | 0.048* | |
| Cl1C | 0.47593 (17) | 0.55631 (10) | 0.87226 (9) | 0.0723 (6) | |
| C1C | 0.4109 (5) | 0.6421 (2) | 0.8598 (3) | 0.068 (2) | |
| H1C1 | 0.3867 | 0.6620 | 0.8997 | 0.082* | |
| H1C2 | 0.4759 | 0.6755 | 0.8312 | 0.082* | |
| Cl2C | 0.27935 (18) | 0.64103 (10) | 0.82890 (11) | 0.0853 (7) | |
| Cl1D | −0.0460 (8) | 0.3220 (2) | 0.2756 (2) | 0.075 (2) | 0.693 (16) |
| C1D | 0.0112 (11) | 0.2334 (4) | 0.2809 (3) | 0.050 (3) | 0.693 (16) |
| H1D1 | −0.0374 | 0.2030 | 0.2611 | 0.060* | 0.693 (16) |
| H1D2 | 0.1002 | 0.2347 | 0.2571 | 0.060* | 0.693 (16) |
| Cl2D | 0.0030 (13) | 0.1918 (5) | 0.3562 (4) | 0.093 (2) | 0.693 (16) |
| Cl1E | −0.0996 (13) | 0.2932 (12) | 0.2747 (6) | 0.096 (4) | 0.307 (16) |
| C1E | 0.0426 (14) | 0.2746 (15) | 0.2952 (10) | 0.075 (8) | 0.307 (16) |
| H1E1 | 0.1067 | 0.2647 | 0.2580 | 0.090* | 0.307 (16) |
| H1E2 | 0.0711 | 0.3187 | 0.3092 | 0.090* | 0.307 (16) |
| Cl2E | 0.035 (4) | 0.2007 (13) | 0.3534 (9) | 0.109 (9) | 0.307 (16) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ru1A | 0.0150 (2) | 0.0158 (2) | 0.0193 (2) | −0.00084 (17) | −0.00409 (18) | 0.00129 (17) |
| Cl1A | 0.0263 (7) | 0.0180 (7) | 0.0291 (7) | 0.0011 (5) | −0.0106 (6) | −0.0010 (5) |
| Cl2A | 0.0276 (8) | 0.0246 (7) | 0.0232 (7) | −0.0017 (6) | −0.0035 (6) | 0.0065 (5) |
| S1A | 0.0161 (7) | 0.0228 (7) | 0.0237 (7) | 0.0007 (5) | −0.0067 (6) | 0.0000 (6) |
| Si1A | 0.0315 (9) | 0.0294 (9) | 0.0326 (9) | −0.0023 (7) | −0.0132 (7) | −0.0018 (7) |
| O1A | 0.022 (2) | 0.030 (2) | 0.030 (2) | −0.0017 (16) | −0.0065 (16) | −0.0006 (16) |
| O2A | 0.0152 (19) | 0.035 (2) | 0.0273 (19) | −0.0032 (16) | −0.0022 (16) | 0.0034 (16) |
| N1A | 0.020 (2) | 0.013 (2) | 0.025 (2) | 0.0036 (17) | −0.0107 (19) | 0.0009 (18) |
| N2A | 0.018 (2) | 0.019 (2) | 0.017 (2) | 0.0043 (18) | −0.0025 (18) | −0.0018 (18) |
| N3A | 0.018 (2) | 0.014 (2) | 0.021 (2) | −0.0021 (17) | −0.0058 (18) | 0.0002 (17) |
| C1A | 0.027 (3) | 0.028 (3) | 0.019 (3) | 0.006 (2) | −0.005 (2) | 0.002 (2) |
| C2A | 0.047 (4) | 0.033 (4) | 0.025 (3) | 0.009 (3) | −0.010 (3) | −0.012 (3) |
| C3A | 0.043 (4) | 0.022 (3) | 0.046 (4) | 0.003 (3) | −0.020 (3) | −0.010 (3) |
| C4A | 0.030 (3) | 0.016 (3) | 0.045 (4) | −0.004 (2) | −0.014 (3) | 0.004 (2) |
| C5A | 0.017 (3) | 0.020 (3) | 0.032 (3) | 0.000 (2) | −0.012 (2) | 0.003 (2) |
| C6A | 0.023 (3) | 0.017 (3) | 0.026 (3) | 0.000 (2) | 0.001 (2) | 0.001 (2) |
| C7A | 0.017 (3) | 0.014 (3) | 0.027 (3) | 0.005 (2) | −0.010 (2) | 0.000 (2) |
| C8A | 0.023 (3) | 0.014 (3) | 0.021 (3) | 0.003 (2) | −0.002 (2) | −0.004 (2) |
| C9A | 0.021 (3) | 0.027 (3) | 0.023 (3) | 0.008 (2) | −0.007 (2) | −0.001 (2) |
| C10A | 0.012 (3) | 0.045 (4) | 0.031 (3) | 0.000 (2) | −0.004 (2) | −0.004 (3) |
| C11A | 0.015 (3) | 0.028 (3) | 0.029 (3) | −0.003 (2) | 0.001 (2) | −0.002 (2) |
| C12A | 0.021 (3) | 0.021 (3) | 0.026 (3) | −0.004 (2) | 0.000 (2) | 0.000 (2) |
| C13A | 0.017 (3) | 0.020 (3) | 0.022 (3) | 0.003 (2) | −0.002 (2) | −0.004 (2) |
| C14A | 0.027 (3) | 0.018 (3) | 0.024 (3) | 0.000 (2) | −0.006 (2) | 0.001 (2) |
| C15A | 0.016 (3) | 0.021 (3) | 0.022 (3) | 0.002 (2) | −0.004 (2) | 0.000 (2) |
| C16A | 0.026 (3) | 0.017 (3) | 0.024 (3) | −0.001 (2) | −0.011 (2) | 0.002 (2) |
| C17A | 0.032 (3) | 0.027 (3) | 0.022 (3) | −0.004 (3) | −0.006 (3) | 0.002 (2) |
| C18A | 0.025 (3) | 0.028 (3) | 0.025 (3) | −0.001 (2) | −0.006 (2) | 0.001 (2) |
| C19A | 0.023 (3) | 0.023 (3) | 0.021 (3) | 0.000 (2) | −0.003 (2) | 0.003 (2) |
| C20A | 0.022 (3) | 0.047 (4) | 0.041 (4) | −0.008 (3) | −0.006 (3) | 0.018 (3) |
| C21A | 0.029 (4) | 0.065 (5) | 0.097 (6) | 0.009 (3) | 0.016 (4) | 0.029 (4) |
| C22A | 0.058 (5) | 0.106 (6) | 0.072 (5) | −0.058 (5) | −0.024 (4) | 0.021 (5) |
| C23A | 0.032 (4) | 0.054 (4) | 0.052 (4) | −0.012 (3) | −0.002 (3) | 0.027 (3) |
| C24A | 0.024 (3) | 0.030 (3) | 0.035 (3) | −0.003 (2) | −0.016 (3) | 0.006 (2) |
| C25A | 0.048 (4) | 0.036 (4) | 0.076 (5) | 0.002 (3) | −0.034 (4) | 0.011 (3) |
| C26A | 0.034 (4) | 0.050 (4) | 0.060 (4) | 0.011 (3) | −0.020 (3) | −0.009 (3) |
| C27A | 0.045 (4) | 0.048 (4) | 0.039 (3) | 0.001 (3) | −0.025 (3) | −0.002 (3) |
| C28A | 0.061 (5) | 0.043 (4) | 0.035 (3) | 0.006 (3) | −0.009 (3) | −0.007 (3) |
| C29A | 0.041 (4) | 0.045 (4) | 0.085 (5) | −0.008 (3) | −0.032 (4) | 0.003 (4) |
| C30A | 0.049 (4) | 0.026 (3) | 0.040 (3) | −0.009 (3) | −0.006 (3) | −0.003 (3) |
| C31A | 0.022 (3) | 0.039 (3) | 0.034 (3) | 0.005 (2) | −0.014 (3) | −0.009 (3) |
| C32A | 0.019 (3) | 0.025 (3) | 0.043 (3) | 0.006 (2) | −0.014 (3) | 0.000 (3) |
| Ru1B | 0.0183 (2) | 0.0168 (2) | 0.0210 (2) | 0.00028 (17) | −0.00551 (18) | 0.00220 (17) |
| Cl1B | 0.0285 (8) | 0.0185 (7) | 0.0332 (7) | 0.0010 (5) | −0.0036 (6) | 0.0000 (6) |
| Cl2B | 0.0388 (9) | 0.0288 (8) | 0.0268 (7) | −0.0020 (6) | −0.0106 (6) | 0.0105 (6) |
| S1B | 0.0189 (7) | 0.0261 (8) | 0.0276 (7) | 0.0002 (6) | −0.0048 (6) | 0.0004 (6) |
| Si1B | 0.0317 (10) | 0.0375 (10) | 0.0354 (9) | 0.0037 (7) | −0.0036 (8) | −0.0065 (8) |
| O1B | 0.031 (2) | 0.028 (2) | 0.029 (2) | 0.0044 (17) | −0.0087 (17) | −0.0026 (16) |
| O2B | 0.022 (2) | 0.038 (2) | 0.042 (2) | 0.0010 (17) | −0.0139 (18) | 0.0059 (18) |
| N1B | 0.018 (2) | 0.023 (2) | 0.027 (2) | 0.0021 (18) | −0.0056 (19) | −0.001 (2) |
| N2B | 0.019 (2) | 0.022 (3) | 0.026 (2) | 0.0008 (19) | −0.008 (2) | −0.005 (2) |
| N3B | 0.013 (2) | 0.020 (2) | 0.023 (2) | −0.0010 (17) | −0.0072 (18) | 0.0022 (18) |
| C1B | 0.021 (3) | 0.030 (3) | 0.025 (3) | −0.005 (2) | −0.004 (2) | 0.005 (2) |
| C2B | 0.041 (4) | 0.030 (3) | 0.031 (3) | −0.003 (3) | −0.008 (3) | −0.009 (3) |
| C3B | 0.031 (3) | 0.029 (3) | 0.042 (4) | −0.001 (3) | 0.001 (3) | −0.013 (3) |
| C4B | 0.024 (3) | 0.020 (3) | 0.036 (3) | 0.001 (2) | −0.005 (3) | 0.002 (2) |
| C5B | 0.018 (3) | 0.018 (3) | 0.027 (3) | −0.002 (2) | −0.003 (2) | 0.003 (2) |
| C6B | 0.023 (3) | 0.017 (3) | 0.021 (3) | 0.007 (2) | −0.008 (2) | 0.004 (2) |
| C7B | 0.018 (3) | 0.019 (3) | 0.024 (3) | −0.005 (2) | −0.005 (2) | 0.004 (2) |
| C8B | 0.021 (3) | 0.020 (3) | 0.025 (3) | −0.003 (2) | −0.010 (2) | −0.005 (2) |
| C9B | 0.026 (3) | 0.029 (3) | 0.040 (3) | −0.002 (3) | −0.012 (3) | −0.001 (3) |
| C10B | 0.016 (3) | 0.043 (4) | 0.054 (4) | 0.001 (3) | −0.013 (3) | −0.010 (3) |
| C11B | 0.032 (4) | 0.033 (3) | 0.048 (4) | 0.006 (3) | −0.019 (3) | −0.007 (3) |
| C12B | 0.028 (3) | 0.021 (3) | 0.034 (3) | 0.006 (2) | −0.014 (3) | 0.005 (2) |
| C13B | 0.029 (3) | 0.024 (3) | 0.015 (3) | 0.004 (2) | −0.007 (2) | −0.001 (2) |
| C14B | 0.026 (3) | 0.023 (3) | 0.020 (3) | −0.001 (2) | −0.007 (2) | −0.002 (2) |
| C15B | 0.021 (3) | 0.024 (3) | 0.031 (3) | 0.002 (2) | −0.008 (2) | −0.001 (2) |
| C16B | 0.037 (4) | 0.025 (3) | 0.021 (3) | −0.002 (3) | −0.008 (3) | −0.002 (2) |
| C17B | 0.042 (4) | 0.024 (3) | 0.026 (3) | 0.002 (3) | −0.008 (3) | 0.002 (2) |
| C18B | 0.033 (3) | 0.027 (3) | 0.028 (3) | 0.005 (3) | −0.005 (3) | −0.004 (3) |
| C19B | 0.031 (3) | 0.035 (3) | 0.021 (3) | −0.006 (3) | −0.007 (2) | −0.002 (2) |
| C20B | 0.034 (4) | 0.045 (4) | 0.038 (4) | 0.017 (3) | −0.015 (3) | −0.005 (3) |
| C21B | 0.067 (6) | 0.097 (7) | 0.088 (6) | 0.035 (5) | −0.018 (5) | 0.040 (5) |
| C22B | 0.102 (7) | 0.138 (8) | 0.089 (6) | 0.079 (6) | −0.041 (5) | −0.072 (6) |
| C23B | 0.044 (5) | 0.076 (6) | 0.108 (6) | 0.022 (4) | −0.028 (4) | −0.015 (5) |
| C24B | 0.033 (3) | 0.033 (3) | 0.030 (3) | −0.003 (3) | 0.002 (3) | 0.004 (3) |
| C25B | 0.054 (4) | 0.033 (4) | 0.054 (4) | −0.011 (3) | −0.007 (3) | 0.014 (3) |
| C26B | 0.046 (4) | 0.055 (4) | 0.049 (4) | −0.019 (3) | −0.005 (3) | 0.008 (3) |
| C27B | 0.059 (5) | 0.049 (4) | 0.030 (3) | −0.004 (3) | 0.008 (3) | −0.004 (3) |
| C28B | 0.055 (4) | 0.046 (4) | 0.056 (4) | −0.001 (3) | −0.017 (3) | −0.018 (3) |
| C29B | 0.044 (4) | 0.056 (5) | 0.059 (4) | 0.008 (3) | 0.005 (3) | −0.015 (3) |
| C30B | 0.048 (4) | 0.045 (4) | 0.049 (4) | 0.020 (3) | −0.010 (3) | −0.006 (3) |
| C31B | 0.024 (3) | 0.041 (4) | 0.050 (4) | −0.004 (3) | 0.005 (3) | −0.013 (3) |
| C32B | 0.025 (3) | 0.030 (3) | 0.037 (3) | −0.005 (2) | −0.003 (3) | 0.001 (3) |
| Cl1C | 0.0637 (13) | 0.0573 (12) | 0.0960 (14) | −0.0096 (9) | −0.0320 (11) | 0.0135 (10) |
| C1C | 0.089 (6) | 0.042 (4) | 0.079 (5) | −0.016 (4) | −0.037 (5) | 0.001 (4) |
| Cl2C | 0.0590 (13) | 0.0635 (13) | 0.1423 (19) | 0.0031 (10) | −0.0388 (13) | −0.0191 (13) |
| Cl1D | 0.100 (5) | 0.048 (2) | 0.075 (2) | 0.026 (2) | −0.015 (2) | −0.0104 (17) |
| C1D | 0.065 (8) | 0.042 (5) | 0.044 (4) | 0.013 (5) | −0.007 (5) | −0.017 (4) |
| Cl2D | 0.137 (5) | 0.073 (3) | 0.054 (3) | 0.031 (3) | −0.006 (3) | 0.004 (3) |
| Cl1E | 0.085 (8) | 0.107 (12) | 0.109 (7) | 0.030 (7) | −0.040 (6) | −0.031 (7) |
| C1E | 0.077 (14) | 0.11 (2) | 0.047 (15) | 0.013 (18) | −0.022 (13) | −0.028 (11) |
| Cl2E | 0.17 (2) | 0.115 (13) | 0.045 (8) | 0.076 (13) | −0.028 (9) | −0.038 (7) |
| Ru1A—N1A | 2.060 (4) | S1B—O2B | 1.487 (4) |
| Ru1A—N2A | 2.105 (4) | S1B—C32B | 1.787 (5) |
| Ru1A—N3A | 2.151 (4) | S1B—C31B | 1.788 (5) |
| Ru1A—S1A | 2.2359 (14) | Si1B—O1B | 1.680 (4) |
| Ru1A—Cl2A | 2.4293 (13) | Si1B—C30B | 1.846 (6) |
| Ru1A—Cl1A | 2.4371 (12) | Si1B—C28B | 1.850 (6) |
| S1A—O2A | 1.496 (3) | Si1B—C29B | 1.858 (6) |
| S1A—C32A | 1.780 (5) | O1B—C15B | 1.391 (6) |
| S1A—C31A | 1.790 (5) | N1B—C1B | 1.356 (6) |
| Si1A—O1A | 1.670 (3) | N1B—C5B | 1.361 (6) |
| Si1A—C30A | 1.837 (5) | N2B—C12B | 1.341 (6) |
| Si1A—C28A | 1.850 (5) | N2B—C8B | 1.366 (6) |
| Si1A—C29A | 1.868 (6) | N3B—C6B | 1.492 (6) |
| O1A—C15A | 1.397 (5) | N3B—C7B | 1.498 (5) |
| N1A—C1A | 1.333 (6) | N3B—C13B | 1.510 (5) |
| N1A—C5A | 1.368 (5) | C1B—C2B | 1.391 (7) |
| N2A—C8A | 1.344 (6) | C1B—H1BA | 0.9500 |
| N2A—C12A | 1.349 (5) | C2B—C3B | 1.385 (7) |
| N3A—C6A | 1.495 (5) | C2B—H2BB | 0.9500 |
| N3A—C13A | 1.514 (5) | C3B—C4B | 1.402 (7) |
| N3A—C7A | 1.514 (6) | C3B—H3BA | 0.9500 |
| C1A—C2A | 1.370 (6) | C4B—C5B | 1.384 (6) |
| C1A—H1AA | 0.9500 | C4B—H4BA | 0.9500 |
| C2A—C3A | 1.365 (7) | C5B—C6B | 1.506 (6) |
| C2A—H2AB | 0.9500 | C6B—H6BA | 0.9900 |
| C3A—C4A | 1.378 (7) | C6B—H6BB | 0.9900 |
| C3A—H3AA | 0.9500 | C7B—C8B | 1.485 (7) |
| C4A—C5A | 1.399 (6) | C7B—H7BA | 0.9900 |
| C4A—H4AA | 0.9500 | C7B—H7BB | 0.9900 |
| C5A—C6A | 1.515 (6) | C8B—C9B | 1.372 (7) |
| C6A—H6AA | 0.9900 | C9B—C10B | 1.395 (7) |
| C6A—H6AB | 0.9900 | C9B—H9BA | 0.9500 |
| C7A—C8A | 1.492 (6) | C10B—C11B | 1.394 (7) |
| C7A—H7AA | 0.9900 | C10B—H10B | 0.9500 |
| C7A—H7AB | 0.9900 | C11B—C12B | 1.377 (7) |
| C8A—C9A | 1.383 (7) | C11B—H11A | 0.9500 |
| C9A—C10A | 1.380 (6) | C12B—H12A | 0.9500 |
| C9A—H9AA | 0.9500 | C13B—C14B | 1.495 (6) |
| C10A—C11A | 1.393 (7) | C13B—H13C | 0.9900 |
| C10A—H10A | 0.9500 | C13B—H13D | 0.9900 |
| C11A—C12A | 1.376 (6) | C14B—C19B | 1.389 (7) |
| C11A—H11B | 0.9500 | C14B—C15B | 1.400 (6) |
| C12A—H12B | 0.9500 | C15B—C16B | 1.422 (7) |
| C13A—C14A | 1.519 (6) | C16B—C17B | 1.385 (7) |
| C13A—H13A | 0.9900 | C16B—C24B | 1.561 (7) |
| C13A—H13B | 0.9900 | C17B—C18B | 1.386 (7) |
| C14A—C19A | 1.397 (6) | C17B—H17B | 0.9500 |
| C14A—C15A | 1.411 (7) | C18B—C19B | 1.383 (7) |
| C15A—C16A | 1.399 (6) | C18B—C20B | 1.538 (7) |
| C16A—C17A | 1.404 (6) | C19B—H19B | 0.9500 |
| C16A—C24A | 1.544 (7) | C20B—C21B | 1.504 (8) |
| C17A—C18A | 1.383 (7) | C20B—C22B | 1.508 (8) |
| C17A—H17A | 0.9500 | C20B—C23B | 1.521 (8) |
| C18A—C19A | 1.387 (6) | C21B—H21D | 0.9800 |
| C18A—C20A | 1.523 (7) | C21B—H21E | 0.9800 |
| C19A—H19A | 0.9500 | C21B—H21F | 0.9800 |
| C20A—C22A | 1.513 (8) | C22B—H22D | 0.9800 |
| C20A—C23A | 1.529 (7) | C22B—H22E | 0.9800 |
| C20A—C21A | 1.545 (8) | C22B—H22F | 0.9800 |
| C21A—H21A | 0.9800 | C23B—H23D | 0.9800 |
| C21A—H21B | 0.9800 | C23B—H23E | 0.9800 |
| C21A—H21C | 0.9800 | C23B—H23F | 0.9800 |
| C22A—H22A | 0.9800 | C24B—C26B | 1.529 (8) |
| C22A—H22B | 0.9800 | C24B—C27B | 1.535 (7) |
| C22A—H22C | 0.9800 | C24B—C25B | 1.537 (7) |
| C23A—H23A | 0.9800 | C25B—H25D | 0.9800 |
| C23A—H23B | 0.9800 | C25B—H25E | 0.9800 |
| C23A—H23C | 0.9800 | C25B—H25F | 0.9800 |
| C24A—C26A | 1.528 (7) | C26B—H26D | 0.9800 |
| C24A—C27A | 1.532 (7) | C26B—H26E | 0.9800 |
| C24A—C25A | 1.551 (7) | C26B—H26F | 0.9800 |
| C25A—H25A | 0.9800 | C27B—H27D | 0.9800 |
| C25A—H25B | 0.9800 | C27B—H27E | 0.9800 |
| C25A—H25C | 0.9800 | C27B—H27F | 0.9800 |
| C26A—H26A | 0.9800 | C28B—H28D | 0.9800 |
| C26A—H26B | 0.9800 | C28B—H28E | 0.9800 |
| C26A—H26C | 0.9800 | C28B—H28F | 0.9800 |
| C27A—H27A | 0.9800 | C29B—H29D | 0.9800 |
| C27A—H27B | 0.9800 | C29B—H29E | 0.9800 |
| C27A—H27C | 0.9800 | C29B—H29F | 0.9800 |
| C28A—H28A | 0.9800 | C30B—H30D | 0.9800 |
| C28A—H28B | 0.9800 | C30B—H30E | 0.9800 |
| C28A—H28C | 0.9800 | C30B—H30F | 0.9800 |
| C29A—H29A | 0.9800 | C31B—H31D | 0.9800 |
| C29A—H29B | 0.9800 | C31B—H31E | 0.9800 |
| C29A—H29C | 0.9800 | C31B—H31F | 0.9800 |
| C30A—H30A | 0.9800 | C32B—H32D | 0.9800 |
| C30A—H30B | 0.9800 | C32B—H32E | 0.9800 |
| C30A—H30C | 0.9800 | C32B—H32F | 0.9800 |
| C31A—H31A | 0.9800 | Cl1C—C1C | 1.738 (3) |
| C31A—H31B | 0.9800 | C1C—Cl2C | 1.738 (3) |
| C31A—H31C | 0.9800 | C1C—H1C1 | 0.9900 |
| C32A—H32A | 0.9800 | C1C—H1C2 | 0.9900 |
| C32A—H32B | 0.9800 | Cl1D—C1D | 1.739 (3) |
| C32A—H32C | 0.9800 | C1D—Cl2D | 1.737 (4) |
| Ru1B—N1B | 2.052 (4) | C1D—H1D1 | 0.9900 |
| Ru1B—N2B | 2.092 (4) | C1D—H1D2 | 0.9900 |
| Ru1B—N3B | 2.149 (4) | Cl1E—C1E | 1.738 (4) |
| Ru1B—S1B | 2.2324 (14) | C1E—Cl2E | 1.738 (4) |
| Ru1B—Cl2B | 2.4220 (13) | C1E—H1E1 | 0.9900 |
| Ru1B—Cl1B | 2.4320 (13) | C1E—H1E2 | 0.9900 |
| N1A—Ru1A—N2A | 96.38 (15) | S1B—Ru1B—Cl2B | 89.29 (5) |
| N1A—Ru1A—N3A | 77.42 (14) | N1B—Ru1B—Cl1B | 175.87 (12) |
| N2A—Ru1A—N3A | 79.17 (14) | N2B—Ru1B—Cl1B | 84.96 (11) |
| N1A—Ru1A—S1A | 88.67 (11) | N3B—Ru1B—Cl1B | 97.72 (11) |
| N2A—Ru1A—S1A | 174.29 (10) | S1B—Ru1B—Cl1B | 89.06 (5) |
| N3A—Ru1A—S1A | 99.43 (11) | Cl2B—Ru1B—Cl1B | 90.20 (5) |
| N1A—Ru1A—Cl2A | 94.58 (11) | O2B—S1B—C32B | 106.0 (2) |
| N2A—Ru1A—Cl2A | 93.85 (10) | O2B—S1B—C31B | 105.7 (2) |
| N3A—Ru1A—Cl2A | 168.59 (11) | C32B—S1B—C31B | 97.9 (2) |
| S1A—Ru1A—Cl2A | 88.38 (5) | O2B—S1B—Ru1B | 118.80 (14) |
| N1A—Ru1A—Cl1A | 176.16 (11) | C32B—S1B—Ru1B | 112.96 (18) |
| N2A—Ru1A—Cl1A | 84.67 (10) | C31B—S1B—Ru1B | 113.15 (18) |
| N3A—Ru1A—Cl1A | 99.19 (10) | O1B—Si1B—C30B | 112.1 (2) |
| S1A—Ru1A—Cl1A | 90.12 (4) | O1B—Si1B—C28B | 107.8 (2) |
| Cl2A—Ru1A—Cl1A | 89.03 (4) | C30B—Si1B—C28B | 110.0 (3) |
| O2A—S1A—C32A | 105.4 (2) | O1B—Si1B—C29B | 107.9 (2) |
| O2A—S1A—C31A | 106.6 (2) | C30B—Si1B—C29B | 104.9 (3) |
| C32A—S1A—C31A | 98.9 (2) | C28B—Si1B—C29B | 114.1 (3) |
| O2A—S1A—Ru1A | 118.72 (15) | C15B—O1B—Si1B | 130.3 (3) |
| C32A—S1A—Ru1A | 113.44 (16) | C1B—N1B—C5B | 118.4 (4) |
| C31A—S1A—Ru1A | 111.64 (17) | C1B—N1B—Ru1B | 126.7 (3) |
| O1A—Si1A—C30A | 112.6 (2) | C5B—N1B—Ru1B | 114.7 (3) |
| O1A—Si1A—C28A | 108.5 (2) | C12B—N2B—C8B | 118.5 (4) |
| C30A—Si1A—C28A | 108.7 (3) | C12B—N2B—Ru1B | 125.0 (3) |
| O1A—Si1A—C29A | 106.6 (2) | C8B—N2B—Ru1B | 115.6 (3) |
| C30A—Si1A—C29A | 105.4 (3) | C6B—N3B—C7B | 108.0 (3) |
| C28A—Si1A—C29A | 115.1 (3) | C6B—N3B—C13B | 112.2 (4) |
| C15A—O1A—Si1A | 129.6 (3) | C7B—N3B—C13B | 111.2 (3) |
| C1A—N1A—C5A | 118.2 (4) | C6B—N3B—Ru1B | 104.3 (3) |
| C1A—N1A—Ru1A | 127.2 (3) | C7B—N3B—Ru1B | 107.8 (3) |
| C5A—N1A—Ru1A | 114.2 (3) | C13B—N3B—Ru1B | 113.0 (3) |
| C8A—N2A—C12A | 118.9 (4) | N1B—C1B—C2B | 122.2 (5) |
| C8A—N2A—Ru1A | 115.5 (3) | N1B—C1B—H1BA | 118.9 |
| C12A—N2A—Ru1A | 123.8 (3) | C2B—C1B—H1BA | 118.9 |
| C6A—N3A—C13A | 112.6 (3) | C3B—C2B—C1B | 119.1 (5) |
| C6A—N3A—C7A | 107.0 (3) | C3B—C2B—H2BB | 120.4 |
| C13A—N3A—C7A | 110.8 (4) | C1B—C2B—H2BB | 120.4 |
| C6A—N3A—Ru1A | 105.0 (3) | C2B—C3B—C4B | 119.1 (5) |
| C13A—N3A—Ru1A | 113.8 (3) | C2B—C3B—H3BA | 120.5 |
| C7A—N3A—Ru1A | 107.1 (3) | C4B—C3B—H3BA | 120.5 |
| N1A—C1A—C2A | 122.3 (5) | C5B—C4B—C3B | 119.0 (5) |
| N1A—C1A—H1AA | 118.8 | C5B—C4B—H4BA | 120.5 |
| C2A—C1A—H1AA | 118.8 | C3B—C4B—H4BA | 120.5 |
| C3A—C2A—C1A | 120.6 (5) | N1B—C5B—C4B | 122.2 (5) |
| C3A—C2A—H2AB | 119.7 | N1B—C5B—C6B | 115.0 (4) |
| C1A—C2A—H2AB | 119.7 | C4B—C5B—C6B | 122.8 (5) |
| C2A—C3A—C4A | 118.5 (5) | N3B—C6B—C5B | 109.1 (4) |
| C2A—C3A—H3AA | 120.8 | N3B—C6B—H6BA | 109.9 |
| C4A—C3A—H3AA | 120.8 | C5B—C6B—H6BA | 109.9 |
| C3A—C4A—C5A | 119.2 (5) | N3B—C6B—H6BB | 109.9 |
| C3A—C4A—H4AA | 120.4 | C5B—C6B—H6BB | 109.9 |
| C5A—C4A—H4AA | 120.4 | H6BA—C6B—H6BB | 108.3 |
| N1A—C5A—C4A | 121.1 (4) | C8B—C7B—N3B | 112.6 (4) |
| N1A—C5A—C6A | 115.5 (4) | C8B—C7B—H7BA | 109.1 |
| C4A—C5A—C6A | 123.4 (4) | N3B—C7B—H7BA | 109.1 |
| N3A—C6A—C5A | 107.8 (3) | C8B—C7B—H7BB | 109.1 |
| N3A—C6A—H6AA | 110.1 | N3B—C7B—H7BB | 109.1 |
| C5A—C6A—H6AA | 110.1 | H7BA—C7B—H7BB | 107.8 |
| N3A—C6A—H6AB | 110.1 | N2B—C8B—C9B | 121.7 (5) |
| C5A—C6A—H6AB | 110.1 | N2B—C8B—C7B | 115.1 (4) |
| H6AA—C6A—H6AB | 108.5 | C9B—C8B—C7B | 123.1 (4) |
| C8A—C7A—N3A | 109.6 (4) | C8B—C9B—C10B | 119.2 (5) |
| C8A—C7A—H7AA | 109.8 | C8B—C9B—H9BA | 120.4 |
| N3A—C7A—H7AA | 109.8 | C10B—C9B—H9BA | 120.4 |
| C8A—C7A—H7AB | 109.8 | C11B—C10B—C9B | 119.1 (5) |
| N3A—C7A—H7AB | 109.8 | C11B—C10B—H10B | 120.4 |
| H7AA—C7A—H7AB | 108.2 | C9B—C10B—H10B | 120.4 |
| N2A—C8A—C9A | 122.1 (4) | C12B—C11B—C10B | 118.4 (5) |
| N2A—C8A—C7A | 115.4 (4) | C12B—C11B—H11A | 120.8 |
| C9A—C8A—C7A | 122.5 (4) | C10B—C11B—H11A | 120.8 |
| C10A—C9A—C8A | 119.1 (5) | N2B—C12B—C11B | 123.0 (5) |
| C10A—C9A—H9AA | 120.5 | N2B—C12B—H12A | 118.5 |
| C8A—C9A—H9AA | 120.5 | C11B—C12B—H12A | 118.5 |
| C9A—C10A—C11A | 118.9 (5) | C14B—C13B—N3B | 115.2 (4) |
| C9A—C10A—H10A | 120.5 | C14B—C13B—H13C | 108.5 |
| C11A—C10A—H10A | 120.5 | N3B—C13B—H13C | 108.5 |
| C12A—C11A—C10A | 119.0 (4) | C14B—C13B—H13D | 108.5 |
| C12A—C11A—H11B | 120.5 | N3B—C13B—H13D | 108.5 |
| C10A—C11A—H11B | 120.5 | H13C—C13B—H13D | 107.5 |
| N2A—C12A—C11A | 122.0 (5) | C19B—C14B—C15B | 118.8 (5) |
| N2A—C12A—H12B | 119.0 | C19B—C14B—C13B | 116.8 (4) |
| C11A—C12A—H12B | 119.0 | C15B—C14B—C13B | 124.4 (5) |
| N3A—C13A—C14A | 115.2 (4) | O1B—C15B—C14B | 118.4 (4) |
| N3A—C13A—H13A | 108.5 | O1B—C15B—C16B | 121.6 (4) |
| C14A—C13A—H13A | 108.5 | C14B—C15B—C16B | 120.0 (5) |
| N3A—C13A—H13B | 108.5 | C17B—C16B—C15B | 116.9 (5) |
| C14A—C13A—H13B | 108.5 | C17B—C16B—C24B | 119.9 (5) |
| H13A—C13A—H13B | 107.5 | C15B—C16B—C24B | 123.1 (5) |
| C19A—C14A—C15A | 119.2 (4) | C16B—C17B—C18B | 124.7 (5) |
| C19A—C14A—C13A | 118.1 (4) | C16B—C17B—H17B | 117.7 |
| C15A—C14A—C13A | 122.7 (4) | C18B—C17B—H17B | 117.7 |
| O1A—C15A—C16A | 121.4 (4) | C19B—C18B—C17B | 116.1 (5) |
| O1A—C15A—C14A | 118.0 (4) | C19B—C18B—C20B | 119.9 (5) |
| C16A—C15A—C14A | 120.6 (4) | C17B—C18B—C20B | 123.8 (5) |
| C15A—C16A—C17A | 116.3 (5) | C18B—C19B—C14B | 123.1 (5) |
| C15A—C16A—C24A | 123.8 (4) | C18B—C19B—H19B | 118.4 |
| C17A—C16A—C24A | 119.8 (4) | C14B—C19B—H19B | 118.4 |
| C18A—C17A—C16A | 124.7 (5) | C21B—C20B—C22B | 109.9 (6) |
| C18A—C17A—H17A | 117.6 | C21B—C20B—C23B | 106.7 (5) |
| C16A—C17A—H17A | 117.6 | C22B—C20B—C23B | 108.2 (6) |
| C17A—C18A—C19A | 116.7 (5) | C21B—C20B—C18B | 112.9 (5) |
| C17A—C18A—C20A | 123.5 (5) | C22B—C20B—C18B | 109.0 (5) |
| C19A—C18A—C20A | 119.8 (5) | C23B—C20B—C18B | 110.1 (5) |
| C18A—C19A—C14A | 121.6 (5) | C20B—C21B—H21D | 109.5 |
| C18A—C19A—H19A | 119.2 | C20B—C21B—H21E | 109.5 |
| C14A—C19A—H19A | 119.2 | H21D—C21B—H21E | 109.5 |
| C22A—C20A—C18A | 110.3 (5) | C20B—C21B—H21F | 109.5 |
| C22A—C20A—C23A | 109.0 (5) | H21D—C21B—H21F | 109.5 |
| C18A—C20A—C23A | 112.6 (5) | H21E—C21B—H21F | 109.5 |
| C22A—C20A—C21A | 108.9 (6) | C20B—C22B—H22D | 109.5 |
| C18A—C20A—C21A | 108.9 (5) | C20B—C22B—H22E | 109.5 |
| C23A—C20A—C21A | 107.0 (5) | H22D—C22B—H22E | 109.5 |
| C20A—C21A—H21A | 109.5 | C20B—C22B—H22F | 109.5 |
| C20A—C21A—H21B | 109.5 | H22D—C22B—H22F | 109.5 |
| H21A—C21A—H21B | 109.5 | H22E—C22B—H22F | 109.5 |
| C20A—C21A—H21C | 109.5 | C20B—C23B—H23D | 109.5 |
| H21A—C21A—H21C | 109.5 | C20B—C23B—H23E | 109.5 |
| H21B—C21A—H21C | 109.5 | H23D—C23B—H23E | 109.5 |
| C20A—C22A—H22A | 109.5 | C20B—C23B—H23F | 109.5 |
| C20A—C22A—H22B | 109.5 | H23D—C23B—H23F | 109.5 |
| H22A—C22A—H22B | 109.5 | H23E—C23B—H23F | 109.5 |
| C20A—C22A—H22C | 109.5 | C26B—C24B—C27B | 110.5 (5) |
| H22A—C22A—H22C | 109.5 | C26B—C24B—C25B | 107.5 (4) |
| H22B—C22A—H22C | 109.5 | C27B—C24B—C25B | 106.8 (5) |
| C20A—C23A—H23A | 109.5 | C26B—C24B—C16B | 111.5 (4) |
| C20A—C23A—H23B | 109.5 | C27B—C24B—C16B | 109.1 (4) |
| H23A—C23A—H23B | 109.5 | C25B—C24B—C16B | 111.3 (5) |
| C20A—C23A—H23C | 109.5 | C24B—C25B—H25D | 109.5 |
| H23A—C23A—H23C | 109.5 | C24B—C25B—H25E | 109.5 |
| H23B—C23A—H23C | 109.5 | H25D—C25B—H25E | 109.5 |
| C26A—C24A—C27A | 109.8 (4) | C24B—C25B—H25F | 109.5 |
| C26A—C24A—C16A | 111.3 (4) | H25D—C25B—H25F | 109.5 |
| C27A—C24A—C16A | 109.8 (4) | H25E—C25B—H25F | 109.5 |
| C26A—C24A—C25A | 106.6 (5) | C24B—C26B—H26D | 109.5 |
| C27A—C24A—C25A | 106.6 (4) | C24B—C26B—H26E | 109.5 |
| C16A—C24A—C25A | 112.6 (4) | H26D—C26B—H26E | 109.5 |
| C24A—C25A—H25A | 109.5 | C24B—C26B—H26F | 109.5 |
| C24A—C25A—H25B | 109.5 | H26D—C26B—H26F | 109.5 |
| H25A—C25A—H25B | 109.5 | H26E—C26B—H26F | 109.5 |
| C24A—C25A—H25C | 109.5 | C24B—C27B—H27D | 109.5 |
| H25A—C25A—H25C | 109.5 | C24B—C27B—H27E | 109.5 |
| H25B—C25A—H25C | 109.5 | H27D—C27B—H27E | 109.5 |
| C24A—C26A—H26A | 109.5 | C24B—C27B—H27F | 109.5 |
| C24A—C26A—H26B | 109.5 | H27D—C27B—H27F | 109.5 |
| H26A—C26A—H26B | 109.5 | H27E—C27B—H27F | 109.5 |
| C24A—C26A—H26C | 109.5 | Si1B—C28B—H28D | 109.5 |
| H26A—C26A—H26C | 109.5 | Si1B—C28B—H28E | 109.5 |
| H26B—C26A—H26C | 109.5 | H28D—C28B—H28E | 109.5 |
| C24A—C27A—H27A | 109.5 | Si1B—C28B—H28F | 109.5 |
| C24A—C27A—H27B | 109.5 | H28D—C28B—H28F | 109.5 |
| H27A—C27A—H27B | 109.5 | H28E—C28B—H28F | 109.5 |
| C24A—C27A—H27C | 109.5 | Si1B—C29B—H29D | 109.5 |
| H27A—C27A—H27C | 109.5 | Si1B—C29B—H29E | 109.5 |
| H27B—C27A—H27C | 109.5 | H29D—C29B—H29E | 109.5 |
| Si1A—C28A—H28A | 109.5 | Si1B—C29B—H29F | 109.5 |
| Si1A—C28A—H28B | 109.5 | H29D—C29B—H29F | 109.5 |
| H28A—C28A—H28B | 109.5 | H29E—C29B—H29F | 109.5 |
| Si1A—C28A—H28C | 109.5 | Si1B—C30B—H30D | 109.5 |
| H28A—C28A—H28C | 109.5 | Si1B—C30B—H30E | 109.5 |
| H28B—C28A—H28C | 109.5 | H30D—C30B—H30E | 109.5 |
| Si1A—C29A—H29A | 109.5 | Si1B—C30B—H30F | 109.5 |
| Si1A—C29A—H29B | 109.5 | H30D—C30B—H30F | 109.5 |
| H29A—C29A—H29B | 109.5 | H30E—C30B—H30F | 109.5 |
| Si1A—C29A—H29C | 109.5 | S1B—C31B—H31D | 109.5 |
| H29A—C29A—H29C | 109.5 | S1B—C31B—H31E | 109.5 |
| H29B—C29A—H29C | 109.5 | H31D—C31B—H31E | 109.5 |
| Si1A—C30A—H30A | 109.5 | S1B—C31B—H31F | 109.5 |
| Si1A—C30A—H30B | 109.5 | H31D—C31B—H31F | 109.5 |
| H30A—C30A—H30B | 109.5 | H31E—C31B—H31F | 109.5 |
| Si1A—C30A—H30C | 109.5 | S1B—C32B—H32D | 109.5 |
| H30A—C30A—H30C | 109.5 | S1B—C32B—H32E | 109.5 |
| H30B—C30A—H30C | 109.5 | H32D—C32B—H32E | 109.5 |
| S1A—C31A—H31A | 109.5 | S1B—C32B—H32F | 109.5 |
| S1A—C31A—H31B | 109.5 | H32D—C32B—H32F | 109.5 |
| H31A—C31A—H31B | 109.5 | H32E—C32B—H32F | 109.5 |
| S1A—C31A—H31C | 109.5 | Cl2C—C1C—Cl1C | 113.6 (3) |
| H31A—C31A—H31C | 109.5 | Cl2C—C1C—H1C1 | 108.9 |
| H31B—C31A—H31C | 109.5 | Cl1C—C1C—H1C1 | 108.9 |
| S1A—C32A—H32A | 109.5 | Cl2C—C1C—H1C2 | 108.9 |
| S1A—C32A—H32B | 109.5 | Cl1C—C1C—H1C2 | 108.9 |
| H32A—C32A—H32B | 109.5 | H1C1—C1C—H1C2 | 107.7 |
| S1A—C32A—H32C | 109.5 | Cl2D—C1D—Cl1D | 114.3 (4) |
| H32A—C32A—H32C | 109.5 | Cl2D—C1D—H1D1 | 108.7 |
| H32B—C32A—H32C | 109.5 | Cl1D—C1D—H1D1 | 108.7 |
| N1B—Ru1B—N2B | 95.09 (15) | Cl2D—C1D—H1D2 | 108.7 |
| N1B—Ru1B—N3B | 78.23 (15) | Cl1D—C1D—H1D2 | 108.7 |
| N2B—Ru1B—N3B | 80.17 (15) | H1D1—C1D—H1D2 | 107.6 |
| N1B—Ru1B—S1B | 90.67 (11) | Cl2E—C1E—Cl1E | 114.2 (5) |
| N2B—Ru1B—S1B | 173.35 (11) | Cl2E—C1E—H1E1 | 108.7 |
| N3B—Ru1B—S1B | 97.80 (10) | Cl1E—C1E—H1E1 | 108.7 |
| N1B—Ru1B—Cl2B | 93.91 (12) | Cl2E—C1E—H1E2 | 108.7 |
| N2B—Ru1B—Cl2B | 93.62 (12) | Cl1E—C1E—H1E2 | 108.7 |
| N3B—Ru1B—Cl2B | 169.41 (10) | H1E1—C1E—H1E2 | 107.6 |
| N1A—Ru1A—S1A—O2A | 90.25 (19) | N1B—Ru1B—S1B—O2B | −93.0 (2) |
| N2A—Ru1A—S1A—O2A | −62.1 (11) | N2B—Ru1B—S1B—O2B | 57.0 (10) |
| N3A—Ru1A—S1A—O2A | 13.23 (18) | N3B—Ru1B—S1B—O2B | −14.8 (2) |
| Cl2A—Ru1A—S1A—O2A | −175.14 (16) | Cl2B—Ru1B—S1B—O2B | 173.09 (17) |
| Cl1A—Ru1A—S1A—O2A | −86.11 (16) | Cl1B—Ru1B—S1B—O2B | 82.88 (17) |
| N1A—Ru1A—S1A—C32A | −145.1 (2) | N1B—Ru1B—S1B—C32B | 141.9 (2) |
| N2A—Ru1A—S1A—C32A | 62.6 (11) | N2B—Ru1B—S1B—C32B | −68.0 (10) |
| N3A—Ru1A—S1A—C32A | 137.9 (2) | N3B—Ru1B—S1B—C32B | −139.8 (2) |
| Cl2A—Ru1A—S1A—C32A | −50.49 (19) | Cl2B—Ru1B—S1B—C32B | 48.03 (19) |
| Cl1A—Ru1A—S1A—C32A | 38.54 (19) | Cl1B—Ru1B—S1B—C32B | −42.18 (19) |
| N1A—Ru1A—S1A—C31A | −34.4 (2) | N1B—Ru1B—S1B—C31B | 31.8 (2) |
| N2A—Ru1A—S1A—C31A | 173.2 (11) | N2B—Ru1B—S1B—C31B | −178.2 (10) |
| N3A—Ru1A—S1A—C31A | −111.4 (2) | N3B—Ru1B—S1B—C31B | 110.0 (2) |
| Cl2A—Ru1A—S1A—C31A | 60.20 (19) | Cl2B—Ru1B—S1B—C31B | −62.1 (2) |
| Cl1A—Ru1A—S1A—C31A | 149.22 (19) | Cl1B—Ru1B—S1B—C31B | −152.3 (2) |
| C30A—Si1A—O1A—C15A | −110.8 (4) | C30B—Si1B—O1B—C15B | 115.5 (4) |
| C28A—Si1A—O1A—C15A | 9.6 (5) | C28B—Si1B—O1B—C15B | −5.7 (5) |
| C29A—Si1A—O1A—C15A | 134.1 (4) | C29B—Si1B—O1B—C15B | −129.4 (4) |
| N2A—Ru1A—N1A—C1A | −83.3 (4) | N2B—Ru1B—N1B—C1B | 82.5 (4) |
| N3A—Ru1A—N1A—C1A | −160.7 (4) | N3B—Ru1B—N1B—C1B | 161.4 (4) |
| S1A—Ru1A—N1A—C1A | 99.3 (4) | S1B—Ru1B—N1B—C1B | −100.8 (4) |
| Cl2A—Ru1A—N1A—C1A | 11.1 (4) | Cl2B—Ru1B—N1B—C1B | −11.5 (4) |
| Cl1A—Ru1A—N1A—C1A | 170.9 (14) | Cl1B—Ru1B—N1B—C1B | 172.9 (13) |
| N2A—Ru1A—N1A—C5A | 104.0 (3) | N2B—Ru1B—N1B—C5B | −102.7 (3) |
| N3A—Ru1A—N1A—C5A | 26.6 (3) | N3B—Ru1B—N1B—C5B | −23.8 (3) |
| S1A—Ru1A—N1A—C5A | −73.4 (3) | S1B—Ru1B—N1B—C5B | 74.0 (3) |
| Cl2A—Ru1A—N1A—C5A | −161.6 (3) | Cl2B—Ru1B—N1B—C5B | 163.3 (3) |
| Cl1A—Ru1A—N1A—C5A | −1.8 (19) | Cl1B—Ru1B—N1B—C5B | −12.3 (17) |
| N1A—Ru1A—N2A—C8A | −70.1 (3) | N1B—Ru1B—N2B—C12B | −118.2 (4) |
| N3A—Ru1A—N2A—C8A | 5.8 (3) | N3B—Ru1B—N2B—C12B | 164.7 (4) |
| S1A—Ru1A—N2A—C8A | 82.1 (12) | S1B—Ru1B—N2B—C12B | 91.9 (11) |
| Cl2A—Ru1A—N2A—C8A | −165.1 (3) | Cl2B—Ru1B—N2B—C12B | −23.9 (4) |
| Cl1A—Ru1A—N2A—C8A | 106.2 (3) | Cl1B—Ru1B—N2B—C12B | 65.9 (4) |
| N1A—Ru1A—N2A—C12A | 125.4 (4) | N1B—Ru1B—N2B—C8B | 73.1 (3) |
| N3A—Ru1A—N2A—C12A | −158.7 (4) | N3B—Ru1B—N2B—C8B | −4.0 (3) |
| S1A—Ru1A—N2A—C12A | −82.4 (12) | S1B—Ru1B—N2B—C8B | −76.8 (11) |
| Cl2A—Ru1A—N2A—C12A | 30.4 (3) | Cl2B—Ru1B—N2B—C8B | 167.4 (3) |
| Cl1A—Ru1A—N2A—C12A | −58.3 (3) | Cl1B—Ru1B—N2B—C8B | −102.7 (3) |
| N1A—Ru1A—N3A—C6A | −38.5 (3) | N1B—Ru1B—N3B—C6B | 36.4 (3) |
| N2A—Ru1A—N3A—C6A | −137.6 (3) | N2B—Ru1B—N3B—C6B | 133.8 (3) |
| S1A—Ru1A—N3A—C6A | 48.0 (3) | S1B—Ru1B—N3B—C6B | −52.6 (3) |
| Cl2A—Ru1A—N3A—C6A | −84.7 (6) | Cl2B—Ru1B—N3B—C6B | 79.1 (7) |
| Cl1A—Ru1A—N3A—C6A | 139.7 (3) | Cl1B—Ru1B—N3B—C6B | −142.7 (2) |
| N1A—Ru1A—N3A—C13A | −162.1 (3) | N1B—Ru1B—N3B—C7B | −78.2 (3) |
| N2A—Ru1A—N3A—C13A | 98.7 (3) | N2B—Ru1B—N3B—C7B | 19.1 (3) |
| S1A—Ru1A—N3A—C13A | −75.6 (3) | S1B—Ru1B—N3B—C7B | −167.3 (3) |
| Cl2A—Ru1A—N3A—C13A | 151.7 (4) | Cl2B—Ru1B—N3B—C7B | −35.5 (8) |
| Cl1A—Ru1A—N3A—C13A | 16.0 (3) | Cl1B—Ru1B—N3B—C7B | 102.6 (3) |
| N1A—Ru1A—N3A—C7A | 75.0 (3) | N1B—Ru1B—N3B—C13B | 158.6 (3) |
| N2A—Ru1A—N3A—C7A | −24.1 (3) | N2B—Ru1B—N3B—C13B | −104.1 (3) |
| S1A—Ru1A—N3A—C7A | 161.5 (2) | S1B—Ru1B—N3B—C13B | 69.5 (3) |
| Cl2A—Ru1A—N3A—C7A | 28.9 (7) | Cl2B—Ru1B—N3B—C13B | −158.8 (5) |
| Cl1A—Ru1A—N3A—C7A | −106.8 (2) | Cl1B—Ru1B—N3B—C13B | −20.6 (3) |
| C5A—N1A—C1A—C2A | 2.0 (8) | C5B—N1B—C1B—C2B | −2.7 (7) |
| Ru1A—N1A—C1A—C2A | −170.5 (4) | Ru1B—N1B—C1B—C2B | 171.9 (3) |
| N1A—C1A—C2A—C3A | 0.2 (9) | N1B—C1B—C2B—C3B | 1.2 (7) |
| C1A—C2A—C3A—C4A | −2.4 (9) | C1B—C2B—C3B—C4B | 1.0 (7) |
| C2A—C3A—C4A—C5A | 2.5 (8) | C2B—C3B—C4B—C5B | −1.5 (7) |
| C1A—N1A—C5A—C4A | −1.9 (7) | C1B—N1B—C5B—C4B | 2.2 (6) |
| Ru1A—N1A—C5A—C4A | 171.5 (4) | Ru1B—N1B—C5B—C4B | −173.1 (3) |
| C1A—N1A—C5A—C6A | 178.4 (4) | C1B—N1B—C5B—C6B | −179.9 (4) |
| Ru1A—N1A—C5A—C6A | −8.2 (5) | Ru1B—N1B—C5B—C6B | 4.8 (5) |
| C3A—C4A—C5A—N1A | −0.3 (8) | C3B—C4B—C5B—N1B | −0.1 (7) |
| C3A—C4A—C5A—C6A | 179.4 (5) | C3B—C4B—C5B—C6B | −177.8 (4) |
| C13A—N3A—C6A—C5A | 168.6 (4) | C7B—N3B—C6B—C5B | 70.7 (4) |
| C7A—N3A—C6A—C5A | −69.5 (5) | C13B—N3B—C6B—C5B | −166.4 (3) |
| Ru1A—N3A—C6A—C5A | 44.1 (4) | Ru1B—N3B—C6B—C5B | −43.8 (4) |
| N1A—C5A—C6A—N3A | −25.5 (6) | N1B—C5B—C6B—N3B | 27.7 (5) |
| C4A—C5A—C6A—N3A | 154.8 (5) | C4B—C5B—C6B—N3B | −154.4 (4) |
| C6A—N3A—C7A—C8A | 150.5 (4) | C6B—N3B—C7B—C8B | −143.7 (4) |
| C13A—N3A—C7A—C8A | −86.4 (4) | C13B—N3B—C7B—C8B | 92.8 (5) |
| Ru1A—N3A—C7A—C8A | 38.3 (4) | Ru1B—N3B—C7B—C8B | −31.5 (4) |
| C12A—N2A—C8A—C9A | −1.1 (7) | C12B—N2B—C8B—C9B | 0.6 (7) |
| Ru1A—N2A—C8A—C9A | −166.4 (3) | Ru1B—N2B—C8B—C9B | 170.0 (4) |
| C12A—N2A—C8A—C7A | −179.4 (4) | C12B—N2B—C8B—C7B | 177.4 (4) |
| Ru1A—N2A—C8A—C7A | 15.3 (5) | Ru1B—N2B—C8B—C7B | −13.1 (5) |
| N3A—C7A—C8A—N2A | −36.5 (5) | N3B—C7B—C8B—N2B | 30.5 (6) |
| N3A—C7A—C8A—C9A | 145.2 (4) | N3B—C7B—C8B—C9B | −152.7 (4) |
| N2A—C8A—C9A—C10A | 0.6 (7) | N2B—C8B—C9B—C10B | 0.3 (7) |
| C7A—C8A—C9A—C10A | 178.8 (4) | C7B—C8B—C9B—C10B | −176.3 (5) |
| C8A—C9A—C10A—C11A | 0.3 (7) | C8B—C9B—C10B—C11B | −1.2 (8) |
| C9A—C10A—C11A—C12A | −0.6 (7) | C9B—C10B—C11B—C12B | 1.2 (8) |
| C8A—N2A—C12A—C11A | 0.8 (7) | C8B—N2B—C12B—C11B | −0.6 (7) |
| Ru1A—N2A—C12A—C11A | 164.8 (3) | Ru1B—N2B—C12B—C11B | −169.0 (4) |
| C10A—C11A—C12A—N2A | 0.0 (7) | C10B—C11B—C12B—N2B | −0.3 (8) |
| C6A—N3A—C13A—C14A | 59.5 (5) | C6B—N3B—C13B—C14B | −53.5 (5) |
| C7A—N3A—C13A—C14A | −60.2 (5) | C7B—N3B—C13B—C14B | 67.6 (5) |
| Ru1A—N3A—C13A—C14A | 179.0 (3) | Ru1B—N3B—C13B—C14B | −171.1 (3) |
| N3A—C13A—C14A—C19A | −90.4 (5) | N3B—C13B—C14B—C19B | 84.7 (5) |
| N3A—C13A—C14A—C15A | 87.5 (5) | N3B—C13B—C14B—C15B | −94.8 (6) |
| Si1A—O1A—C15A—C16A | −97.0 (5) | Si1B—O1B—C15B—C14B | −79.7 (6) |
| Si1A—O1A—C15A—C14A | 84.5 (5) | Si1B—O1B—C15B—C16B | 102.6 (5) |
| C19A—C14A—C15A—O1A | −172.9 (4) | C19B—C14B—C15B—O1B | 174.8 (4) |
| C13A—C14A—C15A—O1A | 9.2 (7) | C13B—C14B—C15B—O1B | −5.7 (7) |
| C19A—C14A—C15A—C16A | 8.5 (7) | C19B—C14B—C15B—C16B | −7.4 (7) |
| C13A—C14A—C15A—C16A | −169.4 (4) | C13B—C14B—C15B—C16B | 172.0 (4) |
| O1A—C15A—C16A—C17A | 173.0 (4) | O1B—C15B—C16B—C17B | −176.8 (4) |
| C14A—C15A—C16A—C17A | −8.5 (7) | C14B—C15B—C16B—C17B | 5.6 (7) |
| O1A—C15A—C16A—C24A | −9.7 (7) | O1B—C15B—C16B—C24B | 1.7 (7) |
| C14A—C15A—C16A—C24A | 168.8 (4) | C14B—C15B—C16B—C24B | −176.0 (4) |
| C15A—C16A—C17A—C18A | 1.3 (7) | C15B—C16B—C17B—C18B | −0.9 (8) |
| C24A—C16A—C17A—C18A | −176.1 (5) | C24B—C16B—C17B—C18B | −179.4 (5) |
| C16A—C17A—C18A—C19A | 5.7 (8) | C16B—C17B—C18B—C19B | −1.8 (8) |
| C16A—C17A—C18A—C20A | −177.3 (5) | C16B—C17B—C18B—C20B | −177.4 (5) |
| C17A—C18A—C19A—C14A | −5.7 (7) | C17B—C18B—C19B—C14B | −0.2 (8) |
| C20A—C18A—C19A—C14A | 177.1 (5) | C20B—C18B—C19B—C14B | 175.6 (5) |
| C15A—C14A—C19A—C18A | −1.1 (7) | C15B—C14B—C19B—C18B | 4.8 (8) |
| C13A—C14A—C19A—C18A | 176.9 (4) | C13B—C14B—C19B—C18B | −174.7 (4) |
| C17A—C18A—C20A—C22A | −115.9 (6) | C19B—C18B—C20B—C21B | 177.0 (5) |
| C19A—C18A—C20A—C22A | 61.1 (7) | C17B—C18B—C20B—C21B | −7.5 (8) |
| C17A—C18A—C20A—C23A | 6.1 (8) | C19B—C18B—C20B—C22B | −60.6 (7) |
| C19A—C18A—C20A—C23A | −176.9 (5) | C17B—C18B—C20B—C22B | 114.9 (6) |
| C17A—C18A—C20A—C21A | 124.6 (6) | C19B—C18B—C20B—C23B | 57.9 (7) |
| C19A—C18A—C20A—C21A | −58.4 (7) | C17B—C18B—C20B—C23B | −126.6 (6) |
| C15A—C16A—C24A—C26A | −42.8 (6) | C17B—C16B—C24B—C26B | −136.2 (5) |
| C17A—C16A—C24A—C26A | 134.5 (5) | C15B—C16B—C24B—C26B | 45.4 (7) |
| C15A—C16A—C24A—C27A | 79.0 (6) | C17B—C16B—C24B—C27B | 101.4 (6) |
| C17A—C16A—C24A—C27A | −103.8 (5) | C15B—C16B—C24B—C27B | −77.0 (6) |
| C15A—C16A—C24A—C25A | −162.4 (5) | C17B—C16B—C24B—C25B | −16.1 (7) |
| C17A—C16A—C24A—C25A | 14.8 (7) | C15B—C16B—C24B—C25B | 165.4 (5) |
The donors of the Petroleum Research Fund, administered by the American Chemical Society (ACS-PRF 48003-UFS), supported this research. PJF is grateful to Henry S. LaPierre and Victor G. Young, Jr for their expertise, and to the John Arnold research group for their hospitality.
Bratsos, I., Serli, B., Zangrando, E., Katsaros, N. & Alessio, E. (2007). Inorg. Chem., 46, 975–992.
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chomitz, W. A. & Arnold, J. (2009). Chem. Eur. J. 15, 2020–2030.
Chomitz, W. A., Minasian, S. G., Sutton, A. D. & Arnold, J. (2007). Inorg. Chem. 46, 7199–7209.
Marinescu, S. C., Agapie, T., Day, M. W. & Bercaw, J. E. (2007). Organometallics, 26, 1178–1190.
Mola, J., Romero, I., Rodriguez, M., Bozoglian, F., Poater, A., Sola, M., Parella, T., Benet-Buchholz, J., Fontrodona, X. & Llobet, A. (2007). Inorg. Chem. 46, 10707–10716.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Velders, A. H., Bergamo, A., Alessio, E., Zangrando, E., Haasnoot, J. G., Casarsa, C., Cocchietto, M., Zorzet, S. & Sava, G. (2004). J. Med. Chem. 47, 1110–1121.
Desilylation of 1 to eliminate the trimethylsilyl substituent with concomitant Ru—O bond formation (and a tetradentate BPPA ligand) has been unsuccessful to date. The utility of BPPA-TMS as a BPPA transfer agent remains an open question.
The distorted octahedral structures at the low spin d6 Ru(II) centers of 1 and cis,fac-[RuCl2(BPEA)(DMSO)] (3, BPEA = N,N-bis(2-pyridylmethyl)ethylamine)) (Mola et al., 2007) are very similar. The sulfur-bound DMSO ligand is cis to the aliphatic nitrogen in both 1 and 3, and the facial binding of the pyridyl and tertiary amine N atoms is seemingly independent tertiary nitrogen steric bulk (i.e., ethyl (3) versus 2-trimethylsiloxo-3,5-tert- butylbenzyl (1)). The average Ru-pyridyl nitrogen lengths (1, 2.077 (3) Å; 3, 2.07 (4) Å) and the average Ru—Cl distances (1, 2.430 (6) Å; 3, 2.435 (9) Å) are statistically indistinguishable. The angles that define the edges of the distorted octahedra range from 79.61 (5) to 99.79 (4)° in 3 to 77.42 (14) to 99.43 (11) in 1. In both structures, the tertiary amine nitrogen-Ru—S angle (defined by N(3 A)—Ru(1 A)—S(1 A) in 1) is most obtuse while angles that define edges occupied by the facially bound ligands are most acute.
The 1H NMR spectra of 1 has similar features to that of 3, and is fully consistent with the solid-state structure. It is noteworthy that the six N—CH2-py and N—CH2—Ph ligand backbone H atoms are diastereotopic; each exhibits a doublet due to geminal coupling.