metal-organic compounds
μ3-Carbonato-κ3O:O′:O′′-tris{(η6-benzene)[(R)-1-(1-aminoethyl)naphthyl-κ2C2,N]ruthenium(II)} hexafluoridophosphate dichloromethane solvate
aInstitut de Chimie de Strasbourg, Université Louis Pasteur, Laboratoire de Synthèses Métallo-Induites, UMR 7177 CNRS, 4 rue Blaise Pascal, 67070 Strasbourg Cedex, France, and bInstitut de Chimie de Strasbourg, Université Louis Pasteur, Service de Radiocristallographie, UMR 7177 CNRS, 4 rue Blaise Pascal, 67070 Strasbourg Cedex, France
*Correspondence e-mail: barloy@chimie.u-strasbg.fr
The title compound, [Ru3(C12H12N)3(CO3)(C6H6)3]PF6·CH2Cl2, was obtained unintentionally as the product of an attempted deprotonation of the monomeric parent ruthenium complex [Ru(C12H12N)(C6H6)(C2H3N)]PF6. The carbonate ligand bridges three half-sandwich cycloruthenated fragments, each of them exhibiting a pseudo-tetrahedral geometry. The configuration of the Ru atoms is S. The naphthyl groups of the enantiopure cycloruthenated benzylic amine ligands point in the same direction, adopting a propeller shape.
Related literature
For related literature, see: Cotton et al. (1992); Demerseman et al. (2006); Lindsay et al. (1987); Maurette et al. (1999); Sortais et al. (2006, 2007).
Experimental
Crystal data
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Data collection
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Data collection: COLLECT (Nonius, 1998); cell DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536808003978/er2047sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808003978/er2047Isup2.hkl
{[(R)-1-(1-naphthyl-κC2)-ethylamine-κN](η6-benzene) (acetonitrile-κN)ruthenium(II)} hexafluorophosphate (31 mg, 58 µmol) (Sortais et al., 2007) was dissolved in 4 ml dichloromethane with 3.3 mg (1 equiv.) ground potassium hydroxide (containing potassium carbonate as minor impurity). The suspension was heated to reflux for 1.5 h and evaporated to dryness. Analysis of a sample dissolved in CD2Cl2 by NMR showed only the signals of the starting material, but single crystals of compound (I) had appeared after letting the tube stand for 3 days at room temperature.
The H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).
Data collection: COLLECT (Nonius, 1998); cell
DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).[Ru3(C12H12N)3(CO3)(C6H6)3]PF6·CH2Cl2 | F(000) = 1344 |
Mr = 1338.12 | Dx = 1.684 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 6871 reflections |
a = 11.4732 (2) Å | θ = 1.0–30.0° |
b = 19.1377 (5) Å | µ = 1.05 mm−1 |
c = 12.0169 (2) Å | T = 173 K |
β = 90.832 (2)° | Prism, yellow |
V = 2638.28 (9) Å3 | 0.12 × 0.10 × 0.08 mm |
Z = 2 |
Nonius KappaCCD diffractometer | 9862 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.050 |
Graphite monochromator | θmax = 30.0°, θmin = 1.7° |
Detector resolution: 10 pixels mm-1 | h = −16→16 |
ϕ and ω scans | k = −24→26 |
15434 measured reflections | l = −16→16 |
12813 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0555P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
12813 reflections | Δρmax = 0.74 e Å−3 |
670 parameters | Δρmin = −0.99 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (3) |
[Ru3(C12H12N)3(CO3)(C6H6)3]PF6·CH2Cl2 | V = 2638.28 (9) Å3 |
Mr = 1338.12 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.4732 (2) Å | µ = 1.05 mm−1 |
b = 19.1377 (5) Å | T = 173 K |
c = 12.0169 (2) Å | 0.12 × 0.10 × 0.08 mm |
β = 90.832 (2)° |
Nonius KappaCCD diffractometer | 9862 reflections with I > 2σ(I) |
15434 measured reflections | Rint = 0.050 |
12813 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.132 | Δρmax = 0.74 e Å−3 |
S = 1.06 | Δρmin = −0.99 e Å−3 |
12813 reflections | Absolute structure: Flack (1983) |
670 parameters | Absolute structure parameter: 0.01 (3) |
1 restraint |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.2995 (5) | 0.8427 (4) | 0.1246 (5) | 0.0201 (13) | |
C2 | 0.3807 (5) | 0.9299 (3) | 0.3937 (5) | 0.0219 (13) | |
C3 | 0.4996 (6) | 0.9276 (4) | 0.4278 (6) | 0.0270 (15) | |
H3 | 0.5538 | 0.9576 | 0.3928 | 0.032* | |
C4 | 0.5389 (7) | 0.8828 (4) | 0.5104 (6) | 0.0375 (19) | |
H4 | 0.6189 | 0.8830 | 0.5318 | 0.045* | |
C5 | 0.4618 (6) | 0.8371 (4) | 0.5629 (5) | 0.0294 (16) | |
C6 | 0.5008 (8) | 0.7871 (5) | 0.6434 (6) | 0.048 (2) | |
H6 | 0.5805 | 0.7860 | 0.6659 | 0.057* | |
C7 | 0.4237 (10) | 0.7409 (5) | 0.6881 (6) | 0.058 (3) | |
H7 | 0.4506 | 0.7083 | 0.7423 | 0.070* | |
C8 | 0.3063 (8) | 0.7404 (5) | 0.6559 (7) | 0.051 (2) | |
H8 | 0.2553 | 0.7067 | 0.6868 | 0.061* | |
C9 | 0.2642 (8) | 0.7874 (4) | 0.5810 (6) | 0.041 (2) | |
H9 | 0.1837 | 0.7869 | 0.5615 | 0.049* | |
C10 | 0.3396 (6) | 0.8376 (4) | 0.5310 (5) | 0.0294 (16) | |
C11 | 0.3028 (5) | 0.8864 (4) | 0.4492 (5) | 0.0220 (14) | |
C12 | 0.1760 (5) | 0.8928 (4) | 0.4189 (5) | 0.0261 (15) | |
H12 | 0.1401 | 0.8453 | 0.4139 | 0.031* | |
C13 | 0.1102 (6) | 0.9370 (5) | 0.5027 (6) | 0.039 (2) | |
H13A | 0.1150 | 0.9148 | 0.5761 | 0.059* | |
H13B | 0.0283 | 0.9409 | 0.4791 | 0.059* | |
H13C | 0.1450 | 0.9837 | 0.5067 | 0.059* | |
C14 | 0.2255 (7) | 1.0778 (5) | 0.2286 (8) | 0.050 (2) | |
H14 | 0.1467 | 1.0869 | 0.2469 | 0.060* | |
C15 | 0.3115 (9) | 1.0883 (5) | 0.3096 (7) | 0.049 (2) | |
H15 | 0.2920 | 1.1069 | 0.3803 | 0.059* | |
C16 | 0.4263 (8) | 1.0714 (5) | 0.2862 (7) | 0.045 (2) | |
H16 | 0.4849 | 1.0788 | 0.3416 | 0.055* | |
C17 | 0.4571 (8) | 1.0442 (5) | 0.1846 (8) | 0.050 (2) | |
H17 | 0.5357 | 1.0315 | 0.1710 | 0.060* | |
C18 | 0.3705 (10) | 1.0354 (5) | 0.1007 (7) | 0.055 (3) | |
H18 | 0.3912 | 1.0170 | 0.0303 | 0.066* | |
C19 | 0.2502 (9) | 1.0543 (4) | 0.1212 (8) | 0.055 (3) | |
H19 | 0.1915 | 1.0509 | 0.0649 | 0.066* | |
C20 | 0.4310 (5) | 0.6561 (3) | 0.1661 (5) | 0.0193 (13) | |
C21 | 0.3938 (5) | 0.6072 (4) | 0.0840 (5) | 0.0208 (14) | |
H21 | 0.4124 | 0.6151 | 0.0083 | 0.025* | |
C22 | 0.3320 (6) | 0.5490 (4) | 0.1122 (5) | 0.0263 (15) | |
H22 | 0.3094 | 0.5172 | 0.0553 | 0.032* | |
C23 | 0.3005 (6) | 0.5347 (4) | 0.2225 (5) | 0.0245 (14) | |
C24 | 0.2331 (6) | 0.4752 (4) | 0.2510 (6) | 0.0357 (17) | |
H24 | 0.2115 | 0.4426 | 0.1948 | 0.043* | |
C25 | 0.1992 (6) | 0.4643 (4) | 0.3569 (6) | 0.0382 (19) | |
H25 | 0.1536 | 0.4244 | 0.3742 | 0.046* | |
C26 | 0.2309 (7) | 0.5115 (4) | 0.4415 (7) | 0.0384 (19) | |
H26 | 0.2047 | 0.5043 | 0.5152 | 0.046* | |
C27 | 0.2986 (6) | 0.5674 (4) | 0.4181 (5) | 0.0290 (16) | |
H27 | 0.3221 | 0.5976 | 0.4769 | 0.035* | |
C28 | 0.3360 (5) | 0.5823 (4) | 0.3077 (5) | 0.0240 (14) | |
C29 | 0.4020 (5) | 0.6425 (4) | 0.2765 (5) | 0.0229 (14) | |
C30 | 0.4463 (6) | 0.6940 (4) | 0.3622 (5) | 0.0249 (15) | |
H30 | 0.3875 | 0.7004 | 0.4220 | 0.030* | |
C31 | 0.5616 (6) | 0.6688 (4) | 0.4123 (6) | 0.0364 (18) | |
H31A | 0.6190 | 0.6639 | 0.3532 | 0.055* | |
H31B | 0.5500 | 0.6235 | 0.4485 | 0.055* | |
H31C | 0.5898 | 0.7028 | 0.4674 | 0.055* | |
C32 | 0.6082 (6) | 0.7174 (4) | −0.0141 (6) | 0.0308 (17) | |
H32 | 0.5918 | 0.6831 | −0.0691 | 0.037* | |
C33 | 0.6721 (5) | 0.6993 (4) | 0.0846 (5) | 0.0273 (16) | |
H33 | 0.6957 | 0.6524 | 0.0977 | 0.033* | |
C34 | 0.6991 (5) | 0.7517 (5) | 0.1618 (5) | 0.0321 (16) | |
H34 | 0.7407 | 0.7400 | 0.2282 | 0.039* | |
C35 | 0.6650 (5) | 0.8231 (4) | 0.1422 (6) | 0.0307 (17) | |
H35 | 0.6865 | 0.8585 | 0.1939 | 0.037* | |
C36 | 0.6011 (6) | 0.8398 (4) | 0.0483 (6) | 0.0295 (16) | |
H36 | 0.5780 | 0.8868 | 0.0352 | 0.035* | |
C37 | 0.5697 (6) | 0.7867 (4) | −0.0290 (6) | 0.0319 (17) | |
H37 | 0.5220 | 0.7981 | −0.0917 | 0.038* | |
C38 | −0.0018 (5) | 0.7922 (4) | 0.1656 (5) | 0.0210 (14) | |
C39 | −0.0630 (5) | 0.8442 (4) | 0.2251 (5) | 0.0228 (14) | |
H39 | −0.0807 | 0.8875 | 0.1901 | 0.027* | |
C40 | −0.0973 (5) | 0.8328 (4) | 0.3329 (5) | 0.0236 (14) | |
H40 | −0.1398 | 0.8681 | 0.3704 | 0.028* | |
C41 | −0.0710 (6) | 0.7704 (4) | 0.3883 (5) | 0.0276 (16) | |
C42 | −0.1033 (7) | 0.7603 (4) | 0.5014 (6) | 0.0367 (18) | |
H42 | −0.1451 | 0.7956 | 0.5396 | 0.044* | |
C43 | −0.0734 (7) | 0.6995 (5) | 0.5543 (6) | 0.042 (2) | |
H43 | −0.0939 | 0.6933 | 0.6299 | 0.051* | |
C44 | −0.0146 (8) | 0.6472 (5) | 0.5006 (6) | 0.044 (2) | |
H44 | 0.0051 | 0.6056 | 0.5397 | 0.053* | |
C45 | 0.0157 (6) | 0.6541 (4) | 0.3920 (6) | 0.0366 (18) | |
H45 | 0.0550 | 0.6171 | 0.3556 | 0.044* | |
C46 | −0.0113 (6) | 0.7170 (4) | 0.3325 (5) | 0.0251 (14) | |
C47 | 0.0225 (5) | 0.7292 (4) | 0.2197 (5) | 0.0227 (14) | |
C48 | 0.0813 (6) | 0.6732 (4) | 0.1515 (6) | 0.0286 (16) | |
H48 | 0.1427 | 0.6501 | 0.1987 | 0.034* | |
C49 | −0.0024 (7) | 0.6186 (4) | 0.1104 (7) | 0.042 (2) | |
H49A | −0.0612 | 0.6403 | 0.0616 | 0.063* | |
H49B | −0.0408 | 0.5968 | 0.1739 | 0.063* | |
H49C | 0.0401 | 0.5829 | 0.0688 | 0.063* | |
C50 | 0.0522 (9) | 0.8959 (5) | −0.1028 (7) | 0.053 (3) | |
H50 | 0.0912 | 0.9393 | −0.0929 | 0.063* | |
C51 | 0.1030 (7) | 0.8457 (6) | −0.1663 (6) | 0.044 (2) | |
H51 | 0.1732 | 0.8556 | −0.2041 | 0.053* | |
C52 | 0.0537 (8) | 0.7825 (5) | −0.1752 (6) | 0.045 (2) | |
H52 | 0.0903 | 0.7479 | −0.2193 | 0.053* | |
C53 | −0.0490 (8) | 0.7661 (5) | −0.1221 (7) | 0.050 (2) | |
H53 | −0.0800 | 0.7202 | −0.1265 | 0.060* | |
C54 | −0.1065 (6) | 0.8179 (7) | −0.0621 (6) | 0.059 (3) | |
H54 | −0.1792 | 0.8083 | −0.0283 | 0.070* | |
C55 | −0.0543 (10) | 0.8858 (6) | −0.0522 (7) | 0.062 (3) | |
H55 | −0.0913 | 0.9223 | −0.0125 | 0.075* | |
C56 | 0.6094 (7) | 0.4920 (5) | 0.2644 (7) | 0.046 (2) | |
H56A | 0.6005 | 0.4719 | 0.3398 | 0.055* | |
H56B | 0.5462 | 0.5265 | 0.2523 | 0.055* | |
N1 | 0.1666 (4) | 0.9289 (3) | 0.3070 (4) | 0.0247 (12) | |
H1A | 0.1069 | 0.9609 | 0.3098 | 0.030* | |
H1B | 0.1462 | 0.8960 | 0.2543 | 0.030* | |
N2 | 0.4657 (5) | 0.7614 (3) | 0.3023 (4) | 0.0262 (13) | |
H2A | 0.5237 | 0.7858 | 0.3389 | 0.031* | |
H2B | 0.3986 | 0.7876 | 0.3054 | 0.031* | |
N3 | 0.1387 (4) | 0.7088 (3) | 0.0559 (4) | 0.0232 (12) | |
H3A | 0.1368 | 0.6791 | −0.0044 | 0.028* | |
H3B | 0.2157 | 0.7164 | 0.0744 | 0.028* | |
O1 | 0.3648 (3) | 0.8835 (2) | 0.1831 (3) | 0.0203 (9) | |
O2 | 0.3397 (4) | 0.7824 (2) | 0.0963 (4) | 0.0234 (10) | |
O3 | 0.1951 (3) | 0.8604 (2) | 0.0977 (3) | 0.0218 (10) | |
F1 | 0.0698 (6) | 0.5255 (4) | 0.8771 (4) | 0.093 (2) | |
F2 | 0.2357 (5) | 0.4880 (4) | 0.8156 (7) | 0.110 (3) | |
F3 | 0.2403 (6) | 0.5770 (4) | 0.6939 (5) | 0.089 (2) | |
F4 | 0.2240 (5) | 0.5996 (3) | 0.8724 (4) | 0.0723 (18) | |
F5 | 0.0723 (5) | 0.6159 (3) | 0.7598 (6) | 0.086 (2) | |
F6 | 0.0852 (5) | 0.5061 (3) | 0.6993 (4) | 0.0566 (15) | |
P1 | 0.15655 (17) | 0.55228 (11) | 0.78605 (15) | 0.0312 (4) | |
Cl1 | 0.5964 (2) | 0.42565 (14) | 0.1657 (2) | 0.0600 (6) | |
Cl2 | 0.74437 (19) | 0.53430 (14) | 0.2568 (2) | 0.0589 (6) | |
Ru1 | 0.31904 (4) | 0.98086 (3) | 0.25393 (4) | 0.02012 (12) | |
Ru2 | 0.51234 (4) | 0.74976 (3) | 0.13391 (4) | 0.01916 (12) | |
Ru3 | 0.06260 (4) | 0.80527 (3) | 0.00783 (4) | 0.02022 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.021 (3) | 0.024 (4) | 0.016 (3) | 0.003 (3) | 0.002 (2) | 0.003 (3) |
C2 | 0.027 (3) | 0.012 (3) | 0.027 (3) | 0.000 (3) | 0.001 (2) | −0.004 (3) |
C3 | 0.024 (3) | 0.020 (4) | 0.037 (4) | −0.003 (3) | −0.001 (3) | −0.002 (3) |
C4 | 0.039 (4) | 0.030 (5) | 0.043 (4) | 0.002 (4) | −0.019 (3) | −0.009 (4) |
C5 | 0.046 (4) | 0.021 (4) | 0.021 (3) | 0.008 (3) | −0.003 (3) | −0.010 (3) |
C6 | 0.079 (6) | 0.040 (6) | 0.023 (4) | 0.024 (5) | −0.014 (4) | −0.006 (4) |
C7 | 0.128 (9) | 0.028 (5) | 0.019 (4) | 0.019 (6) | 0.015 (5) | 0.006 (4) |
C8 | 0.074 (7) | 0.036 (5) | 0.044 (5) | 0.011 (5) | 0.025 (4) | 0.011 (4) |
C9 | 0.061 (5) | 0.027 (5) | 0.034 (4) | 0.006 (4) | 0.021 (4) | 0.009 (3) |
C10 | 0.045 (4) | 0.026 (4) | 0.017 (3) | 0.002 (3) | 0.007 (3) | −0.004 (3) |
C11 | 0.025 (3) | 0.017 (3) | 0.024 (3) | 0.002 (3) | 0.004 (2) | −0.004 (3) |
C12 | 0.021 (3) | 0.026 (4) | 0.032 (4) | −0.007 (3) | 0.007 (3) | 0.002 (3) |
C13 | 0.035 (4) | 0.054 (6) | 0.030 (4) | 0.005 (4) | 0.006 (3) | −0.012 (4) |
C14 | 0.038 (5) | 0.019 (4) | 0.092 (7) | 0.011 (4) | 0.001 (4) | 0.000 (5) |
C15 | 0.076 (7) | 0.026 (5) | 0.046 (5) | −0.018 (4) | 0.007 (4) | −0.008 (4) |
C16 | 0.053 (5) | 0.028 (5) | 0.055 (5) | −0.020 (4) | −0.016 (4) | 0.008 (4) |
C17 | 0.046 (5) | 0.027 (5) | 0.078 (6) | −0.005 (4) | 0.020 (4) | 0.017 (5) |
C18 | 0.111 (9) | 0.026 (5) | 0.028 (4) | −0.016 (5) | 0.015 (5) | 0.011 (4) |
C19 | 0.075 (7) | 0.021 (5) | 0.068 (6) | −0.010 (5) | −0.047 (5) | 0.017 (5) |
C20 | 0.017 (3) | 0.013 (3) | 0.029 (3) | 0.005 (2) | 0.001 (2) | −0.001 (3) |
C21 | 0.019 (3) | 0.025 (4) | 0.019 (3) | 0.004 (3) | −0.004 (2) | −0.002 (3) |
C22 | 0.025 (3) | 0.026 (4) | 0.028 (3) | −0.001 (3) | −0.009 (3) | −0.008 (3) |
C23 | 0.024 (3) | 0.019 (4) | 0.030 (3) | −0.002 (3) | −0.006 (3) | −0.002 (3) |
C24 | 0.030 (4) | 0.027 (4) | 0.050 (4) | −0.015 (3) | −0.008 (3) | 0.001 (4) |
C25 | 0.036 (4) | 0.027 (4) | 0.052 (5) | −0.002 (3) | 0.006 (3) | 0.016 (4) |
C26 | 0.035 (4) | 0.033 (5) | 0.047 (5) | 0.005 (4) | 0.011 (3) | 0.013 (4) |
C27 | 0.032 (4) | 0.028 (4) | 0.027 (3) | 0.009 (3) | 0.003 (3) | −0.001 (3) |
C28 | 0.022 (3) | 0.021 (4) | 0.029 (3) | 0.007 (3) | 0.002 (3) | 0.002 (3) |
C29 | 0.020 (3) | 0.027 (4) | 0.022 (3) | 0.005 (3) | 0.002 (2) | 0.001 (3) |
C30 | 0.033 (4) | 0.023 (4) | 0.019 (3) | −0.002 (3) | 0.003 (3) | −0.001 (3) |
C31 | 0.044 (5) | 0.037 (5) | 0.028 (4) | 0.005 (4) | −0.013 (3) | −0.004 (4) |
C32 | 0.030 (4) | 0.027 (4) | 0.035 (4) | −0.006 (3) | 0.013 (3) | −0.010 (3) |
C33 | 0.014 (3) | 0.033 (4) | 0.036 (4) | 0.009 (3) | 0.004 (3) | 0.006 (3) |
C34 | 0.013 (3) | 0.046 (5) | 0.037 (4) | −0.003 (3) | −0.006 (2) | 0.004 (4) |
C35 | 0.020 (3) | 0.031 (4) | 0.041 (4) | −0.004 (3) | 0.001 (3) | −0.011 (3) |
C36 | 0.024 (3) | 0.018 (4) | 0.047 (4) | −0.001 (3) | 0.013 (3) | 0.001 (3) |
C37 | 0.027 (4) | 0.040 (5) | 0.029 (4) | 0.002 (3) | 0.003 (3) | 0.004 (3) |
C38 | 0.011 (3) | 0.028 (4) | 0.024 (3) | −0.003 (3) | −0.003 (2) | 0.000 (3) |
C39 | 0.019 (3) | 0.017 (4) | 0.033 (3) | 0.000 (3) | 0.000 (3) | 0.000 (3) |
C40 | 0.017 (3) | 0.027 (4) | 0.027 (3) | −0.002 (3) | 0.007 (2) | −0.004 (3) |
C41 | 0.027 (3) | 0.032 (4) | 0.023 (3) | −0.008 (3) | −0.003 (3) | 0.002 (3) |
C42 | 0.045 (4) | 0.035 (5) | 0.030 (4) | 0.000 (4) | 0.003 (3) | 0.005 (4) |
C43 | 0.057 (5) | 0.050 (6) | 0.020 (4) | −0.017 (4) | −0.001 (3) | 0.011 (4) |
C44 | 0.060 (5) | 0.037 (5) | 0.035 (4) | −0.010 (4) | −0.013 (4) | 0.017 (4) |
C45 | 0.036 (4) | 0.031 (5) | 0.042 (4) | −0.003 (4) | −0.013 (3) | 0.003 (4) |
C46 | 0.026 (3) | 0.025 (4) | 0.024 (3) | −0.004 (3) | −0.006 (3) | 0.002 (3) |
C47 | 0.016 (3) | 0.023 (4) | 0.029 (3) | 0.000 (3) | −0.005 (2) | 0.000 (3) |
C48 | 0.019 (3) | 0.028 (4) | 0.038 (4) | 0.003 (3) | 0.001 (3) | 0.000 (3) |
C49 | 0.047 (5) | 0.027 (4) | 0.052 (5) | −0.006 (4) | 0.012 (4) | −0.011 (4) |
C50 | 0.074 (7) | 0.033 (5) | 0.051 (5) | −0.017 (5) | −0.032 (5) | 0.016 (4) |
C51 | 0.037 (4) | 0.068 (7) | 0.027 (4) | −0.005 (4) | 0.006 (3) | 0.009 (4) |
C52 | 0.052 (5) | 0.057 (6) | 0.024 (4) | 0.009 (5) | −0.004 (3) | −0.014 (4) |
C53 | 0.064 (6) | 0.041 (6) | 0.044 (5) | −0.027 (5) | −0.027 (4) | 0.008 (4) |
C54 | 0.019 (4) | 0.132 (11) | 0.025 (4) | 0.011 (5) | −0.008 (3) | 0.020 (6) |
C55 | 0.083 (7) | 0.077 (8) | 0.027 (4) | 0.063 (7) | −0.021 (4) | −0.010 (5) |
C56 | 0.045 (5) | 0.036 (5) | 0.057 (5) | 0.007 (4) | 0.018 (4) | 0.004 (4) |
N1 | 0.022 (3) | 0.027 (3) | 0.025 (3) | −0.007 (2) | 0.000 (2) | −0.005 (3) |
N2 | 0.025 (3) | 0.022 (4) | 0.031 (3) | 0.000 (2) | −0.003 (2) | −0.003 (3) |
N3 | 0.019 (3) | 0.019 (3) | 0.032 (3) | 0.000 (2) | −0.005 (2) | −0.005 (3) |
O1 | 0.018 (2) | 0.016 (2) | 0.026 (2) | 0.0002 (18) | −0.0048 (17) | −0.0036 (19) |
O2 | 0.019 (2) | 0.018 (2) | 0.033 (2) | 0.0031 (18) | −0.0012 (18) | −0.005 (2) |
O3 | 0.013 (2) | 0.024 (3) | 0.029 (2) | 0.0024 (18) | −0.0031 (16) | −0.005 (2) |
F1 | 0.136 (6) | 0.097 (6) | 0.046 (3) | −0.046 (5) | 0.032 (3) | −0.005 (3) |
F2 | 0.069 (4) | 0.042 (4) | 0.219 (8) | 0.009 (4) | −0.056 (5) | 0.001 (5) |
F3 | 0.115 (5) | 0.082 (5) | 0.072 (4) | −0.066 (4) | 0.045 (3) | −0.030 (4) |
F4 | 0.106 (5) | 0.052 (4) | 0.058 (3) | −0.011 (3) | −0.043 (3) | −0.014 (3) |
F5 | 0.064 (4) | 0.034 (3) | 0.158 (6) | 0.011 (3) | −0.037 (4) | −0.001 (4) |
F6 | 0.076 (4) | 0.044 (3) | 0.049 (3) | −0.031 (3) | −0.009 (2) | −0.006 (2) |
P1 | 0.0385 (11) | 0.0268 (11) | 0.0282 (9) | −0.0024 (8) | −0.0040 (8) | −0.0021 (8) |
Cl1 | 0.0737 (16) | 0.0425 (14) | 0.0635 (14) | 0.0017 (13) | −0.0093 (12) | −0.0031 (12) |
Cl2 | 0.0362 (11) | 0.0526 (15) | 0.0879 (17) | −0.0006 (11) | 0.0012 (10) | 0.0091 (14) |
Ru1 | 0.0205 (2) | 0.0170 (3) | 0.0229 (2) | −0.0008 (2) | −0.00081 (18) | −0.0004 (2) |
Ru2 | 0.0149 (2) | 0.0201 (3) | 0.0225 (2) | 0.0010 (2) | −0.00019 (17) | −0.0030 (2) |
Ru3 | 0.0163 (2) | 0.0223 (3) | 0.0221 (2) | 0.0002 (2) | −0.00065 (17) | −0.0025 (2) |
C1—O3 | 1.281 (7) | C33—H33 | 0.9500 |
C1—O1 | 1.284 (8) | C34—C35 | 1.440 (11) |
C1—O2 | 1.291 (8) | C34—Ru2 | 2.165 (6) |
C2—C11 | 1.398 (9) | C34—H34 | 0.9500 |
C2—C3 | 1.419 (9) | C35—C36 | 1.373 (10) |
C2—Ru1 | 2.059 (6) | C35—Ru2 | 2.245 (7) |
C3—C4 | 1.382 (10) | C35—H35 | 0.9500 |
C3—H3 | 0.9500 | C36—C37 | 1.419 (10) |
C4—C5 | 1.400 (11) | C36—Ru2 | 2.257 (7) |
C4—H4 | 0.9500 | C36—H36 | 0.9500 |
C5—C6 | 1.427 (10) | C37—Ru2 | 2.191 (7) |
C5—C10 | 1.449 (10) | C37—H37 | 0.9500 |
C6—C7 | 1.367 (13) | C38—C47 | 1.397 (9) |
C6—H6 | 0.9500 | C38—C39 | 1.417 (9) |
C7—C8 | 1.396 (13) | C38—Ru3 | 2.060 (6) |
C7—H7 | 0.9500 | C39—C40 | 1.376 (9) |
C8—C9 | 1.356 (11) | C39—H39 | 0.9500 |
C8—H8 | 0.9500 | C40—C41 | 1.399 (10) |
C9—C10 | 1.431 (10) | C40—H40 | 0.9500 |
C9—H9 | 0.9500 | C41—C46 | 1.405 (10) |
C10—C11 | 1.415 (9) | C41—C42 | 1.427 (9) |
C11—C12 | 1.500 (9) | C42—C43 | 1.367 (11) |
C12—N1 | 1.514 (8) | C42—H42 | 0.9500 |
C12—C13 | 1.523 (9) | C43—C44 | 1.374 (12) |
C12—H12 | 1.0000 | C43—H43 | 0.9500 |
C13—H13A | 0.9800 | C44—C45 | 1.361 (11) |
C13—H13B | 0.9800 | C44—H44 | 0.9500 |
C13—H13C | 0.9800 | C45—C46 | 1.432 (10) |
C14—C15 | 1.391 (12) | C45—H45 | 0.9500 |
C14—C19 | 1.399 (13) | C46—C47 | 1.433 (9) |
C14—Ru1 | 2.162 (8) | C47—C48 | 1.513 (9) |
C14—H14 | 0.9500 | C48—N3 | 1.497 (9) |
C15—C16 | 1.388 (12) | C48—C49 | 1.499 (10) |
C15—Ru1 | 2.165 (9) | C48—H48 | 1.0000 |
C15—H15 | 0.9500 | C49—H49A | 0.9800 |
C16—C17 | 1.379 (12) | C49—H49B | 0.9800 |
C16—Ru1 | 2.158 (8) | C49—H49C | 0.9800 |
C16—H16 | 0.9500 | C50—C51 | 1.361 (13) |
C17—C18 | 1.415 (13) | C50—C55 | 1.387 (14) |
C17—Ru1 | 2.171 (8) | C50—Ru3 | 2.187 (8) |
C17—H17 | 0.9500 | C50—H50 | 0.9500 |
C18—C19 | 1.451 (14) | C51—C52 | 1.339 (13) |
C18—Ru1 | 2.205 (7) | C51—Ru3 | 2.284 (7) |
C18—H18 | 0.9500 | C51—H51 | 0.9500 |
C19—Ru1 | 2.260 (8) | C52—C53 | 1.383 (12) |
C19—H19 | 0.9500 | C52—Ru3 | 2.243 (7) |
C20—C29 | 1.397 (8) | C52—H52 | 0.9500 |
C20—C21 | 1.421 (9) | C53—C54 | 1.398 (14) |
C20—Ru2 | 2.060 (6) | C53—Ru3 | 2.140 (7) |
C21—C22 | 1.366 (9) | C53—H53 | 0.9500 |
C21—H21 | 0.9500 | C54—C55 | 1.434 (16) |
C22—C23 | 1.405 (9) | C54—Ru3 | 2.117 (7) |
C22—H22 | 0.9500 | C54—H54 | 0.9500 |
C23—C24 | 1.421 (10) | C55—Ru3 | 2.160 (8) |
C23—C28 | 1.427 (9) | C55—H55 | 0.9500 |
C24—C25 | 1.352 (10) | C56—Cl1 | 1.742 (9) |
C24—H24 | 0.9500 | C56—Cl2 | 1.751 (8) |
C25—C26 | 1.405 (11) | C56—H56A | 0.9900 |
C25—H25 | 0.9500 | C56—H56B | 0.9900 |
C26—C27 | 1.353 (10) | N1—Ru1 | 2.119 (5) |
C26—H26 | 0.9500 | N1—H1A | 0.9200 |
C27—C28 | 1.429 (9) | N1—H1B | 0.9200 |
C27—H27 | 0.9500 | N2—Ru2 | 2.112 (5) |
C28—C29 | 1.432 (10) | N2—H2A | 0.9200 |
C29—C30 | 1.508 (9) | N2—H2B | 0.9200 |
C30—N2 | 1.495 (9) | N3—Ru3 | 2.119 (6) |
C30—C31 | 1.523 (10) | N3—H3A | 0.9200 |
C30—H30 | 1.0000 | N3—H3B | 0.9200 |
C31—H31A | 0.9800 | O1—Ru1 | 2.118 (4) |
C31—H31B | 0.9800 | O2—Ru2 | 2.119 (4) |
C31—H31C | 0.9800 | O3—Ru3 | 2.132 (4) |
C32—C37 | 1.409 (10) | F1—P1 | 1.576 (6) |
C32—C33 | 1.428 (10) | F2—P1 | 1.566 (7) |
C32—Ru2 | 2.193 (7) | F3—P1 | 1.551 (5) |
C32—H32 | 0.9500 | F4—P1 | 1.572 (5) |
C33—C34 | 1.397 (10) | F5—P1 | 1.584 (6) |
C33—Ru2 | 2.162 (6) | F6—P1 | 1.585 (5) |
O3—C1—O1 | 120.9 (6) | C47—C48—H48 | 108.7 |
O3—C1—O2 | 120.4 (6) | C48—C49—H49A | 109.5 |
O1—C1—O2 | 118.7 (5) | C48—C49—H49B | 109.5 |
C11—C2—C3 | 117.5 (6) | H49A—C49—H49B | 109.5 |
C11—C2—Ru1 | 117.2 (5) | C48—C49—H49C | 109.5 |
C3—C2—Ru1 | 124.6 (5) | H49A—C49—H49C | 109.5 |
C4—C3—C2 | 121.9 (7) | H49B—C49—H49C | 109.5 |
C4—C3—H3 | 119.0 | C51—C50—C55 | 122.3 (9) |
C2—C3—H3 | 119.0 | C51—C50—Ru3 | 76.2 (5) |
C3—C4—C5 | 120.6 (7) | C55—C50—Ru3 | 70.3 (5) |
C3—C4—H4 | 119.7 | C51—C50—H50 | 118.9 |
C5—C4—H4 | 119.7 | C55—C50—H50 | 118.9 |
C4—C5—C6 | 122.0 (7) | Ru3—C50—H50 | 126.6 |
C4—C5—C10 | 119.5 (6) | C52—C51—C50 | 119.9 (8) |
C6—C5—C10 | 118.5 (7) | C52—C51—Ru3 | 71.1 (5) |
C7—C6—C5 | 120.1 (9) | C50—C51—Ru3 | 68.4 (4) |
C7—C6—H6 | 119.9 | C52—C51—H51 | 120.1 |
C5—C6—H6 | 119.9 | C50—C51—H51 | 120.1 |
C6—C7—C8 | 121.5 (8) | Ru3—C51—H51 | 133.6 |
C6—C7—H7 | 119.2 | C51—C52—C53 | 122.0 (8) |
C8—C7—H7 | 119.2 | C51—C52—Ru3 | 74.5 (5) |
C9—C8—C7 | 120.8 (8) | C53—C52—Ru3 | 67.6 (4) |
C9—C8—H8 | 119.6 | C51—C52—H52 | 119.0 |
C7—C8—H8 | 119.6 | C53—C52—H52 | 119.0 |
C8—C9—C10 | 120.8 (8) | Ru3—C52—H52 | 131.9 |
C8—C9—H9 | 119.6 | C52—C53—C54 | 119.2 (9) |
C10—C9—H9 | 119.6 | C52—C53—Ru3 | 75.7 (5) |
C11—C10—C9 | 124.0 (7) | C54—C53—Ru3 | 69.9 (4) |
C11—C10—C5 | 117.7 (6) | C52—C53—H53 | 120.4 |
C9—C10—C5 | 118.2 (7) | C54—C53—H53 | 120.4 |
C2—C11—C10 | 122.6 (6) | Ru3—C53—H53 | 125.7 |
C2—C11—C12 | 117.4 (6) | C53—C54—C55 | 119.0 (8) |
C10—C11—C12 | 120.0 (6) | C53—C54—Ru3 | 71.7 (4) |
C11—C12—N1 | 108.0 (5) | C55—C54—Ru3 | 72.0 (5) |
C11—C12—C13 | 111.9 (6) | C53—C54—H54 | 120.5 |
N1—C12—C13 | 107.7 (6) | C55—C54—H54 | 120.5 |
C11—C12—H12 | 109.7 | Ru3—C54—H54 | 127.8 |
N1—C12—H12 | 109.7 | C50—C55—C54 | 117.3 (8) |
C13—C12—H12 | 109.7 | C50—C55—Ru3 | 72.5 (5) |
C12—C13—H13A | 109.5 | C54—C55—Ru3 | 68.8 (5) |
C12—C13—H13B | 109.5 | C50—C55—H55 | 121.3 |
H13A—C13—H13B | 109.5 | C54—C55—H55 | 121.3 |
C12—C13—H13C | 109.5 | Ru3—C55—H55 | 129.6 |
H13A—C13—H13C | 109.5 | Cl1—C56—Cl2 | 111.6 (4) |
H13B—C13—H13C | 109.5 | Cl1—C56—H56A | 109.3 |
C15—C14—C19 | 122.7 (8) | Cl2—C56—H56A | 109.3 |
C15—C14—Ru1 | 71.3 (5) | Cl1—C56—H56B | 109.3 |
C19—C14—Ru1 | 75.4 (5) | Cl2—C56—H56B | 109.3 |
C15—C14—H14 | 118.6 | H56A—C56—H56B | 108.0 |
C19—C14—H14 | 118.6 | C12—N1—Ru1 | 115.6 (4) |
Ru1—C14—H14 | 126.7 | C12—N1—H1A | 108.4 |
C16—C15—C14 | 119.3 (8) | Ru1—N1—H1A | 108.4 |
C16—C15—Ru1 | 71.0 (5) | C12—N1—H1B | 108.4 |
C14—C15—Ru1 | 71.1 (5) | Ru1—N1—H1B | 108.4 |
C16—C15—H15 | 120.3 | H1A—N1—H1B | 107.4 |
C14—C15—H15 | 120.3 | C30—N2—Ru2 | 114.4 (4) |
Ru1—C15—H15 | 130.0 | C30—N2—H2A | 108.7 |
C17—C16—C15 | 121.6 (8) | Ru2—N2—H2A | 108.7 |
C17—C16—Ru1 | 71.9 (5) | C30—N2—H2B | 108.7 |
C15—C16—Ru1 | 71.6 (5) | Ru2—N2—H2B | 108.7 |
C17—C16—H16 | 119.2 | H2A—N2—H2B | 107.6 |
C15—C16—H16 | 119.2 | C48—N3—Ru3 | 114.9 (4) |
Ru1—C16—H16 | 129.9 | C48—N3—H3A | 108.5 |
C16—C17—C18 | 119.3 (8) | Ru3—N3—H3A | 108.5 |
C16—C17—Ru1 | 70.9 (5) | C48—N3—H3B | 108.5 |
C18—C17—Ru1 | 72.4 (5) | Ru3—N3—H3B | 108.5 |
C16—C17—H17 | 120.4 | H3A—N3—H3B | 107.5 |
C18—C17—H17 | 120.4 | C1—O1—Ru1 | 127.5 (4) |
Ru1—C17—H17 | 128.5 | C1—O2—Ru2 | 122.9 (4) |
C17—C18—C19 | 120.6 (8) | C1—O3—Ru3 | 130.9 (4) |
C17—C18—Ru1 | 69.8 (4) | F3—P1—F2 | 92.2 (4) |
C19—C18—Ru1 | 73.1 (5) | F3—P1—F4 | 89.5 (3) |
C17—C18—H18 | 119.7 | F2—P1—F4 | 91.4 (3) |
C19—C18—H18 | 119.7 | F3—P1—F1 | 178.3 (4) |
Ru1—C18—H18 | 129.9 | F2—P1—F1 | 87.6 (4) |
C14—C19—C18 | 116.3 (7) | F4—P1—F1 | 92.3 (3) |
C14—C19—Ru1 | 67.8 (5) | F3—P1—F5 | 90.3 (4) |
C18—C19—Ru1 | 69.0 (4) | F2—P1—F5 | 177.5 (4) |
C14—C19—H19 | 121.8 | F4—P1—F5 | 89.0 (3) |
C18—C19—H19 | 121.8 | F1—P1—F5 | 89.9 (4) |
Ru1—C19—H19 | 134.2 | F3—P1—F6 | 91.2 (3) |
C29—C20—C21 | 117.6 (6) | F2—P1—F6 | 90.2 (3) |
C29—C20—Ru2 | 117.1 (5) | F4—P1—F6 | 178.3 (3) |
C21—C20—Ru2 | 125.1 (5) | F1—P1—F6 | 87.1 (3) |
C22—C21—C20 | 121.1 (6) | F5—P1—F6 | 89.4 (3) |
C22—C21—H21 | 119.4 | C2—Ru1—O1 | 80.0 (2) |
C20—C21—H21 | 119.4 | C2—Ru1—N1 | 78.9 (2) |
C21—C22—C23 | 122.3 (6) | O1—Ru1—N1 | 85.3 (2) |
C21—C22—H22 | 118.8 | C2—Ru1—C16 | 92.6 (3) |
C23—C22—H22 | 118.8 | O1—Ru1—C16 | 129.5 (3) |
C22—C23—C24 | 122.2 (6) | N1—Ru1—C16 | 142.6 (3) |
C22—C23—C28 | 118.5 (6) | C2—Ru1—C14 | 133.2 (3) |
C24—C23—C28 | 119.3 (6) | O1—Ru1—C14 | 145.5 (3) |
C25—C24—C23 | 121.0 (7) | N1—Ru1—C14 | 92.0 (3) |
C25—C24—H24 | 119.5 | C16—Ru1—C14 | 67.4 (4) |
C23—C24—H24 | 119.5 | C2—Ru1—C15 | 102.3 (3) |
C24—C25—C26 | 120.4 (7) | O1—Ru1—C15 | 166.3 (3) |
C24—C25—H25 | 119.8 | N1—Ru1—C15 | 108.4 (3) |
C26—C25—H25 | 119.8 | C16—Ru1—C15 | 37.5 (3) |
C27—C26—C25 | 120.1 (7) | C14—Ru1—C15 | 37.5 (3) |
C27—C26—H26 | 120.0 | C2—Ru1—C17 | 109.5 (3) |
C25—C26—H26 | 120.0 | O1—Ru1—C17 | 98.7 (3) |
C26—C27—C28 | 122.2 (7) | N1—Ru1—C17 | 171.2 (3) |
C26—C27—H27 | 118.9 | C16—Ru1—C17 | 37.2 (3) |
C28—C27—H27 | 118.9 | C14—Ru1—C17 | 80.2 (3) |
C23—C28—C27 | 116.9 (7) | C15—Ru1—C17 | 67.7 (3) |
C23—C28—C29 | 118.2 (6) | C2—Ru1—C18 | 144.4 (3) |
C27—C28—C29 | 124.8 (6) | O1—Ru1—C18 | 90.6 (3) |
C20—C29—C28 | 122.2 (6) | N1—Ru1—C18 | 134.9 (3) |
C20—C29—C30 | 116.4 (6) | C16—Ru1—C18 | 67.1 (3) |
C28—C29—C30 | 121.4 (5) | C14—Ru1—C18 | 67.3 (4) |
N2—C30—C29 | 106.6 (5) | C15—Ru1—C18 | 79.7 (3) |
N2—C30—C31 | 109.2 (6) | C17—Ru1—C18 | 37.7 (3) |
C29—C30—C31 | 110.2 (6) | C2—Ru1—C19 | 169.4 (3) |
N2—C30—H30 | 110.3 | O1—Ru1—C19 | 110.5 (3) |
C29—C30—H30 | 110.3 | N1—Ru1—C19 | 102.9 (3) |
C31—C30—H30 | 110.3 | C16—Ru1—C19 | 79.6 (3) |
C30—C31—H31A | 109.5 | C14—Ru1—C19 | 36.8 (4) |
C30—C31—H31B | 109.5 | C15—Ru1—C19 | 67.2 (3) |
H31A—C31—H31B | 109.5 | C17—Ru1—C19 | 68.3 (4) |
C30—C31—H31C | 109.5 | C18—Ru1—C19 | 37.9 (4) |
H31A—C31—H31C | 109.5 | C20—Ru2—N2 | 77.8 (2) |
H31B—C31—H31C | 109.5 | C20—Ru2—O2 | 82.6 (2) |
C37—C32—C33 | 119.4 (7) | N2—Ru2—O2 | 85.66 (19) |
C37—C32—Ru2 | 71.2 (4) | C20—Ru2—C33 | 92.9 (3) |
C33—C32—Ru2 | 69.7 (4) | N2—Ru2—C33 | 122.5 (2) |
C37—C32—H32 | 120.3 | O2—Ru2—C33 | 150.1 (2) |
C33—C32—H32 | 120.3 | C20—Ru2—C34 | 115.9 (3) |
Ru2—C32—H32 | 131.6 | N2—Ru2—C34 | 96.5 (2) |
C34—C33—C32 | 118.9 (7) | O2—Ru2—C34 | 161.5 (3) |
C34—C33—Ru2 | 71.3 (4) | C33—Ru2—C34 | 37.7 (3) |
C32—C33—Ru2 | 72.1 (4) | C20—Ru2—C37 | 126.3 (3) |
C34—C33—H33 | 120.6 | N2—Ru2—C37 | 154.9 (3) |
C32—C33—H33 | 120.6 | O2—Ru2—C37 | 90.4 (2) |
Ru2—C33—H33 | 128.2 | C33—Ru2—C37 | 68.5 (3) |
C33—C34—C35 | 121.0 (6) | C34—Ru2—C37 | 79.8 (3) |
C33—C34—Ru2 | 71.0 (4) | C20—Ru2—C32 | 98.1 (3) |
C35—C34—Ru2 | 74.0 (4) | N2—Ru2—C32 | 160.6 (3) |
C33—C34—H34 | 119.5 | O2—Ru2—C32 | 112.9 (2) |
C35—C34—H34 | 119.5 | C33—Ru2—C32 | 38.3 (3) |
Ru2—C34—H34 | 127.6 | C34—Ru2—C32 | 67.9 (3) |
C36—C35—C34 | 119.7 (7) | C37—Ru2—C32 | 37.5 (3) |
C36—C35—Ru2 | 72.7 (4) | C20—Ru2—C35 | 153.0 (3) |
C34—C35—Ru2 | 67.9 (4) | N2—Ru2—C35 | 95.8 (2) |
C36—C35—H35 | 120.1 | O2—Ru2—C35 | 123.5 (2) |
C34—C35—H35 | 120.1 | C33—Ru2—C35 | 68.1 (3) |
Ru2—C35—H35 | 132.1 | C34—Ru2—C35 | 38.1 (3) |
C35—C36—C37 | 119.9 (7) | C37—Ru2—C35 | 66.0 (3) |
C35—C36—Ru2 | 71.8 (4) | C32—Ru2—C35 | 79.2 (3) |
C37—C36—Ru2 | 68.9 (4) | C20—Ru2—C36 | 163.4 (2) |
C35—C36—H36 | 120.1 | N2—Ru2—C36 | 118.6 (2) |
C37—C36—H36 | 120.1 | O2—Ru2—C36 | 96.0 (2) |
Ru2—C36—H36 | 132.2 | C33—Ru2—C36 | 80.0 (3) |
C32—C37—C36 | 120.9 (7) | C34—Ru2—C36 | 66.7 (3) |
C32—C37—Ru2 | 71.3 (4) | C37—Ru2—C36 | 37.2 (3) |
C36—C37—Ru2 | 73.9 (4) | C32—Ru2—C36 | 67.1 (3) |
C32—C37—H37 | 119.5 | C35—Ru2—C36 | 35.5 (3) |
C36—C37—H37 | 119.5 | C38—Ru3—C54 | 92.3 (3) |
Ru2—C37—H37 | 127.3 | C38—Ru3—N3 | 78.2 (2) |
C47—C38—C39 | 117.9 (5) | C54—Ru3—N3 | 125.4 (4) |
C47—C38—Ru3 | 117.5 (5) | C38—Ru3—O3 | 81.8 (2) |
C39—C38—Ru3 | 124.5 (5) | C54—Ru3—O3 | 141.9 (4) |
C40—C39—C38 | 121.0 (6) | N3—Ru3—O3 | 90.30 (19) |
C40—C39—H39 | 119.5 | C38—Ru3—C53 | 114.2 (3) |
C38—C39—H39 | 119.5 | C54—Ru3—C53 | 38.3 (4) |
C39—C40—C41 | 121.3 (6) | N3—Ru3—C53 | 97.7 (3) |
C39—C40—H40 | 119.3 | O3—Ru3—C53 | 163.2 (3) |
C41—C40—H40 | 119.3 | C38—Ru3—C55 | 99.5 (3) |
C40—C41—C46 | 119.8 (6) | C54—Ru3—C55 | 39.2 (4) |
C40—C41—C42 | 120.7 (7) | N3—Ru3—C55 | 164.6 (4) |
C46—C41—C42 | 119.5 (7) | O3—Ru3—C55 | 104.5 (4) |
C43—C42—C41 | 119.4 (7) | C53—Ru3—C55 | 69.2 (4) |
C43—C42—H42 | 120.3 | C38—Ru3—C50 | 129.7 (4) |
C41—C42—H42 | 120.3 | C54—Ru3—C50 | 68.1 (4) |
C42—C43—C44 | 121.6 (7) | N3—Ru3—C50 | 151.0 (3) |
C42—C43—H43 | 119.2 | O3—Ru3—C50 | 87.0 (2) |
C44—C43—H43 | 119.2 | C53—Ru3—C50 | 78.9 (3) |
C45—C44—C43 | 120.8 (8) | C55—Ru3—C50 | 37.2 (4) |
C45—C44—H44 | 119.6 | C38—Ru3—C52 | 150.1 (3) |
C43—C44—H44 | 119.6 | C54—Ru3—C52 | 66.7 (3) |
C44—C45—C46 | 120.3 (8) | N3—Ru3—C52 | 96.4 (3) |
C44—C45—H45 | 119.8 | O3—Ru3—C52 | 127.9 (3) |
C46—C45—H45 | 119.8 | C53—Ru3—C52 | 36.7 (3) |
C41—C46—C45 | 118.4 (6) | C55—Ru3—C52 | 78.0 (3) |
C41—C46—C47 | 118.3 (6) | C50—Ru3—C52 | 63.7 (4) |
C45—C46—C47 | 123.3 (7) | C38—Ru3—C51 | 164.6 (3) |
C38—C47—C46 | 121.7 (6) | C54—Ru3—C51 | 78.1 (3) |
C38—C47—C48 | 116.5 (6) | N3—Ru3—C51 | 117.2 (3) |
C46—C47—C48 | 121.7 (6) | O3—Ru3—C51 | 98.2 (3) |
N3—C48—C49 | 110.5 (6) | C53—Ru3—C51 | 65.0 (3) |
N3—C48—C47 | 107.4 (6) | C55—Ru3—C51 | 65.5 (3) |
C49—C48—C47 | 112.6 (5) | C50—Ru3—C51 | 35.4 (3) |
N3—C48—H48 | 108.8 | C52—Ru3—C51 | 34.4 (3) |
C49—C48—H48 | 108.8 | ||
C11—C2—C3—C4 | 1.8 (10) | C17—C18—Ru1—C19 | 132.7 (8) |
Ru1—C2—C3—C4 | −168.3 (6) | C14—C19—Ru1—C2 | −23 (2) |
C2—C3—C4—C5 | 0.8 (11) | C18—C19—Ru1—C2 | 109.2 (18) |
C3—C4—C5—C6 | 175.9 (7) | C14—C19—Ru1—O1 | 165.5 (5) |
C3—C4—C5—C10 | −0.8 (11) | C18—C19—Ru1—O1 | −62.5 (5) |
C4—C5—C6—C7 | −176.4 (7) | C14—C19—Ru1—N1 | 75.8 (5) |
C10—C5—C6—C7 | 0.4 (10) | C18—C19—Ru1—N1 | −152.2 (5) |
C5—C6—C7—C8 | 0.9 (12) | C14—C19—Ru1—C16 | −66.1 (6) |
C6—C7—C8—C9 | −1.9 (13) | C18—C19—Ru1—C16 | 65.9 (5) |
C7—C8—C9—C10 | 1.5 (12) | C18—C19—Ru1—C14 | 132.0 (8) |
C8—C9—C10—C11 | 177.5 (7) | C14—C19—Ru1—C15 | −29.1 (5) |
C8—C9—C10—C5 | −0.3 (10) | C18—C19—Ru1—C15 | 102.9 (6) |
C4—C5—C10—C11 | −1.7 (9) | C14—C19—Ru1—C17 | −103.0 (6) |
C6—C5—C10—C11 | −178.6 (6) | C18—C19—Ru1—C17 | 28.9 (5) |
C4—C5—C10—C9 | 176.2 (6) | C14—C19—Ru1—C18 | −132.0 (8) |
C6—C5—C10—C9 | −0.7 (9) | C29—C20—Ru2—N2 | −8.2 (5) |
C3—C2—C11—C10 | −4.5 (10) | C21—C20—Ru2—N2 | 166.5 (6) |
Ru1—C2—C11—C10 | 166.3 (5) | C29—C20—Ru2—O2 | −95.3 (5) |
C3—C2—C11—C12 | 175.6 (6) | C21—C20—Ru2—O2 | 79.4 (5) |
Ru1—C2—C11—C12 | −13.6 (8) | C29—C20—Ru2—C33 | 114.4 (5) |
C9—C10—C11—C2 | −173.2 (6) | C21—C20—Ru2—C33 | −70.9 (5) |
C5—C10—C11—C2 | 4.5 (10) | C29—C20—Ru2—C34 | 83.3 (5) |
C9—C10—C11—C12 | 6.7 (10) | C21—C20—Ru2—C34 | −102.1 (5) |
C5—C10—C11—C12 | −175.6 (6) | C29—C20—Ru2—C37 | 179.7 (4) |
C2—C11—C12—N1 | 18.7 (8) | C21—C20—Ru2—C37 | −5.6 (6) |
C10—C11—C12—N1 | −161.2 (6) | C29—C20—Ru2—C32 | 152.5 (5) |
C2—C11—C12—C13 | −99.7 (7) | C21—C20—Ru2—C32 | −32.8 (6) |
C10—C11—C12—C13 | 80.4 (8) | C29—C20—Ru2—C35 | 70.5 (7) |
C19—C14—C15—C16 | −3.7 (13) | C21—C20—Ru2—C35 | −114.9 (6) |
Ru1—C14—C15—C16 | 54.1 (8) | C29—C20—Ru2—C36 | 178.5 (7) |
C19—C14—C15—Ru1 | −57.7 (8) | C21—C20—Ru2—C36 | −6.9 (12) |
C14—C15—C16—C17 | −0.2 (13) | C30—N2—Ru2—C20 | 22.1 (4) |
Ru1—C15—C16—C17 | 54.0 (8) | C30—N2—Ru2—O2 | 105.5 (4) |
C14—C15—C16—Ru1 | −54.2 (7) | C30—N2—Ru2—C33 | −63.6 (5) |
C15—C16—C17—C18 | 2.1 (13) | C30—N2—Ru2—C34 | −93.0 (5) |
Ru1—C16—C17—C18 | 55.9 (7) | C30—N2—Ru2—C37 | −172.9 (5) |
C15—C16—C17—Ru1 | −53.8 (7) | C30—N2—Ru2—C32 | −57.6 (9) |
C16—C17—C18—C19 | −0.4 (13) | C30—N2—Ru2—C35 | −131.3 (4) |
Ru1—C17—C18—C19 | 54.8 (7) | C30—N2—Ru2—C36 | −160.0 (4) |
C16—C17—C18—Ru1 | −55.2 (7) | C1—O2—Ru2—C20 | 139.6 (5) |
C15—C14—C19—C18 | 5.2 (13) | C1—O2—Ru2—N2 | 61.3 (5) |
Ru1—C14—C19—C18 | −50.7 (7) | C1—O2—Ru2—C33 | −137.4 (5) |
C15—C14—C19—Ru1 | 55.9 (8) | C1—O2—Ru2—C34 | −36.3 (9) |
C17—C18—C19—C14 | −3.1 (12) | C1—O2—Ru2—C37 | −93.8 (5) |
Ru1—C18—C19—C14 | 50.2 (7) | C1—O2—Ru2—C32 | −124.7 (5) |
C17—C18—C19—Ru1 | −53.2 (7) | C1—O2—Ru2—C35 | −32.7 (5) |
C29—C20—C21—C22 | 0.1 (9) | C1—O2—Ru2—C36 | −57.0 (5) |
Ru2—C20—C21—C22 | −174.6 (5) | C34—C33—Ru2—C20 | −130.4 (4) |
C20—C21—C22—C23 | 0.8 (10) | C32—C33—Ru2—C20 | 99.4 (4) |
C21—C22—C23—C24 | 178.1 (7) | C34—C33—Ru2—N2 | −52.9 (5) |
C21—C22—C23—C28 | −0.8 (10) | C32—C33—Ru2—N2 | 176.8 (4) |
C22—C23—C24—C25 | −176.8 (7) | C34—C33—Ru2—O2 | 149.3 (5) |
C28—C23—C24—C25 | 2.0 (11) | C32—C33—Ru2—O2 | 19.1 (7) |
C23—C24—C25—C26 | −0.5 (12) | C32—C33—Ru2—C34 | −130.2 (7) |
C24—C25—C26—C27 | −2.0 (12) | C34—C33—Ru2—C37 | 101.5 (5) |
C25—C26—C27—C28 | 2.8 (11) | C32—C33—Ru2—C37 | −28.7 (4) |
C22—C23—C28—C27 | 177.7 (6) | C34—C33—Ru2—C32 | 130.2 (7) |
C24—C23—C28—C27 | −1.2 (9) | C34—C33—Ru2—C35 | 29.7 (4) |
C22—C23—C28—C29 | 0.0 (9) | C32—C33—Ru2—C35 | −100.5 (5) |
C24—C23—C28—C29 | −178.9 (6) | C34—C33—Ru2—C36 | 64.7 (4) |
C26—C27—C28—C23 | −1.2 (10) | C32—C33—Ru2—C36 | −65.6 (4) |
C26—C27—C28—C29 | 176.3 (7) | C33—C34—Ru2—C20 | 57.7 (5) |
C21—C20—C29—C28 | −0.9 (9) | C35—C34—Ru2—C20 | −170.6 (4) |
Ru2—C20—C29—C28 | 174.2 (5) | C33—C34—Ru2—N2 | 137.3 (4) |
C21—C20—C29—C30 | 177.9 (6) | C35—C34—Ru2—N2 | −91.0 (4) |
Ru2—C20—C29—C30 | −7.0 (7) | C33—C34—Ru2—O2 | −126.8 (7) |
C23—C28—C29—C20 | 0.8 (9) | C35—C34—Ru2—O2 | 4.9 (9) |
C27—C28—C29—C20 | −176.7 (6) | C35—C34—Ru2—C33 | 131.7 (6) |
C23—C28—C29—C30 | −177.9 (6) | C33—C34—Ru2—C37 | −67.8 (4) |
C27—C28—C29—C30 | 4.6 (10) | C35—C34—Ru2—C37 | 63.9 (4) |
C20—C29—C30—N2 | 24.0 (8) | C33—C34—Ru2—C32 | −30.7 (4) |
C28—C29—C30—N2 | −157.2 (6) | C35—C34—Ru2—C32 | 101.0 (5) |
C20—C29—C30—C31 | −94.4 (7) | C33—C34—Ru2—C35 | −131.7 (6) |
C28—C29—C30—C31 | 84.4 (8) | C33—C34—Ru2—C36 | −104.3 (4) |
C37—C32—C33—C34 | −2.8 (9) | C35—C34—Ru2—C36 | 27.4 (4) |
Ru2—C32—C33—C34 | −55.7 (5) | C32—C37—Ru2—C20 | −47.9 (5) |
C37—C32—C33—Ru2 | 52.9 (6) | C36—C37—Ru2—C20 | −179.4 (4) |
C32—C33—C34—C35 | −0.8 (9) | C32—C37—Ru2—N2 | 150.4 (5) |
Ru2—C33—C34—C35 | −56.9 (5) | C36—C37—Ru2—N2 | 19.0 (8) |
C32—C33—C34—Ru2 | 56.1 (5) | C32—C37—Ru2—O2 | −129.0 (4) |
C33—C34—C35—C36 | 2.4 (10) | C36—C37—Ru2—O2 | 99.5 (4) |
Ru2—C34—C35—C36 | −53.1 (6) | C32—C37—Ru2—C33 | 29.3 (4) |
C33—C34—C35—Ru2 | 55.5 (5) | C36—C37—Ru2—C33 | −102.2 (5) |
C34—C35—C36—C37 | −0.3 (10) | C32—C37—Ru2—C34 | 66.8 (5) |
Ru2—C35—C36—C37 | −51.2 (6) | C36—C37—Ru2—C34 | −64.7 (4) |
C34—C35—C36—Ru2 | 50.9 (5) | C36—C37—Ru2—C32 | −131.5 (6) |
C33—C32—C37—C36 | 4.9 (10) | C32—C37—Ru2—C35 | 104.0 (5) |
Ru2—C32—C37—C36 | 57.1 (6) | C36—C37—Ru2—C35 | −27.4 (4) |
C33—C32—C37—Ru2 | −52.2 (6) | C32—C37—Ru2—C36 | 131.5 (6) |
C35—C36—C37—C32 | −3.3 (10) | C37—C32—Ru2—C20 | 142.8 (4) |
Ru2—C36—C37—C32 | −55.9 (6) | C33—C32—Ru2—C20 | −84.4 (4) |
C35—C36—C37—Ru2 | 52.5 (6) | C37—C32—Ru2—N2 | −140.9 (7) |
C47—C38—C39—C40 | 0.1 (9) | C33—C32—Ru2—N2 | −8.1 (10) |
Ru3—C38—C39—C40 | −176.1 (5) | C37—C32—Ru2—O2 | 57.4 (5) |
C38—C39—C40—C41 | 1.4 (10) | C33—C32—Ru2—O2 | −169.8 (4) |
C39—C40—C41—C46 | −1.9 (10) | C37—C32—Ru2—C33 | −132.8 (6) |
C39—C40—C41—C42 | 177.6 (6) | C37—C32—Ru2—C34 | −102.5 (5) |
C40—C41—C42—C43 | −178.2 (7) | C33—C32—Ru2—C34 | 30.3 (4) |
C46—C41—C42—C43 | 1.3 (11) | C33—C32—Ru2—C37 | 132.8 (6) |
C41—C42—C43—C44 | −1.1 (12) | C37—C32—Ru2—C35 | −64.5 (4) |
C42—C43—C44—C45 | −0.2 (13) | C33—C32—Ru2—C35 | 68.3 (4) |
C43—C44—C45—C46 | 1.3 (12) | C37—C32—Ru2—C36 | −29.4 (4) |
C40—C41—C46—C45 | 179.2 (6) | C33—C32—Ru2—C36 | 103.3 (5) |
C42—C41—C46—C45 | −0.3 (10) | C36—C35—Ru2—C20 | 152.2 (5) |
C40—C41—C46—C47 | 1.0 (9) | C34—C35—Ru2—C20 | 18.8 (8) |
C42—C41—C46—C47 | −178.6 (6) | C36—C35—Ru2—N2 | −133.4 (4) |
C44—C45—C46—C41 | −0.9 (10) | C34—C35—Ru2—N2 | 93.3 (4) |
C44—C45—C46—C47 | 177.2 (7) | C36—C35—Ru2—O2 | −44.8 (5) |
C39—C38—C47—C46 | −1.0 (9) | C34—C35—Ru2—O2 | −178.1 (3) |
Ru3—C38—C47—C46 | 175.5 (5) | C36—C35—Ru2—C33 | 103.9 (4) |
C39—C38—C47—C48 | 176.3 (6) | C34—C35—Ru2—C33 | −29.5 (4) |
Ru3—C38—C47—C48 | −7.2 (7) | C36—C35—Ru2—C34 | 133.4 (6) |
C41—C46—C47—C38 | 0.5 (9) | C36—C35—Ru2—C37 | 28.6 (4) |
C45—C46—C47—C38 | −177.7 (6) | C34—C35—Ru2—C37 | −104.7 (5) |
C41—C46—C47—C48 | −176.7 (6) | C36—C35—Ru2—C32 | 65.6 (4) |
C45—C46—C47—C48 | 5.2 (10) | C34—C35—Ru2—C32 | −67.8 (4) |
C38—C47—C48—N3 | 21.1 (8) | C34—C35—Ru2—C36 | −133.4 (6) |
C46—C47—C48—N3 | −161.6 (5) | C35—C36—Ru2—C20 | −131.9 (8) |
C38—C47—C48—C49 | −100.8 (7) | C37—C36—Ru2—C20 | 1.7 (11) |
C46—C47—C48—C49 | 76.5 (8) | C35—C36—Ru2—N2 | 55.5 (5) |
C55—C50—C51—C52 | −4.5 (13) | C37—C36—Ru2—N2 | −171.0 (4) |
Ru3—C50—C51—C52 | 51.1 (8) | C35—C36—Ru2—O2 | 143.8 (4) |
C55—C50—C51—Ru3 | −55.6 (7) | C37—C36—Ru2—O2 | −82.6 (4) |
C50—C51—C52—C53 | 0.4 (13) | C35—C36—Ru2—C33 | −66.2 (4) |
Ru3—C51—C52—C53 | 50.3 (7) | C37—C36—Ru2—C33 | 67.4 (4) |
C50—C51—C52—Ru3 | −49.8 (7) | C35—C36—Ru2—C34 | −29.2 (4) |
C51—C52—C53—C54 | 3.4 (12) | C37—C36—Ru2—C34 | 104.4 (5) |
Ru3—C52—C53—C54 | 56.7 (6) | C35—C36—Ru2—C37 | −133.6 (6) |
C51—C52—C53—Ru3 | −53.3 (8) | C35—C36—Ru2—C32 | −103.9 (5) |
C52—C53—C54—C55 | −3.3 (11) | C37—C36—Ru2—C32 | 29.7 (4) |
Ru3—C53—C54—C55 | 56.3 (6) | C37—C36—Ru2—C35 | 133.6 (6) |
C52—C53—C54—Ru3 | −59.6 (7) | C47—C38—Ru3—C54 | 119.8 (6) |
C51—C50—C55—C54 | 4.5 (12) | C39—C38—Ru3—C54 | −64.0 (6) |
Ru3—C50—C55—C54 | −53.8 (6) | C47—C38—Ru3—N3 | −5.9 (4) |
C51—C50—C55—Ru3 | 58.3 (7) | C39—C38—Ru3—N3 | 170.3 (5) |
C53—C54—C55—C50 | −0.5 (11) | C47—C38—Ru3—O3 | −98.0 (5) |
Ru3—C54—C55—C50 | 55.7 (7) | C39—C38—Ru3—O3 | 78.2 (5) |
C53—C54—C55—Ru3 | −56.2 (6) | C47—C38—Ru3—C53 | 87.3 (5) |
C11—C12—N1—Ru1 | −15.9 (7) | C39—C38—Ru3—C53 | −96.6 (6) |
C13—C12—N1—Ru1 | 105.3 (5) | C47—C38—Ru3—C55 | 158.5 (6) |
C29—C30—N2—Ru2 | −30.4 (6) | C39—C38—Ru3—C55 | −25.3 (6) |
C31—C30—N2—Ru2 | 88.6 (5) | C47—C38—Ru3—C50 | −177.1 (5) |
C49—C48—N3—Ru3 | 97.5 (6) | C39—C38—Ru3—C50 | −0.9 (7) |
C47—C48—N3—Ru3 | −25.7 (6) | C47—C38—Ru3—C52 | 76.3 (7) |
O3—C1—O1—Ru1 | 3.7 (8) | C39—C38—Ru3—C52 | −107.6 (8) |
O2—C1—O1—Ru1 | −174.1 (4) | C47—C38—Ru3—C51 | 170.9 (9) |
O3—C1—O2—Ru2 | 178.5 (4) | C39—C38—Ru3—C51 | −13.0 (14) |
O1—C1—O2—Ru2 | −3.7 (7) | C53—C54—Ru3—C38 | −127.7 (6) |
O1—C1—O3—Ru3 | −177.6 (4) | C55—C54—Ru3—C38 | 102.2 (5) |
O2—C1—O3—Ru3 | 0.2 (8) | C53—C54—Ru3—N3 | −50.5 (6) |
C11—C2—Ru1—O1 | −84.1 (5) | C55—C54—Ru3—N3 | 179.3 (4) |
C3—C2—Ru1—O1 | 86.0 (6) | C53—C54—Ru3—O3 | 152.8 (5) |
C11—C2—Ru1—N1 | 3.0 (5) | C55—C54—Ru3—O3 | 22.6 (7) |
C3—C2—Ru1—N1 | 173.1 (6) | C55—C54—Ru3—C53 | −130.1 (7) |
C11—C2—Ru1—C16 | 146.3 (5) | C53—C54—Ru3—C55 | 130.1 (7) |
C3—C2—Ru1—C16 | −43.6 (6) | C53—C54—Ru3—C50 | 100.0 (6) |
C11—C2—Ru1—C14 | 85.2 (6) | C55—C54—Ru3—C50 | −30.1 (5) |
C3—C2—Ru1—C14 | −104.7 (6) | C53—C54—Ru3—C52 | 30.4 (5) |
C11—C2—Ru1—C15 | 109.7 (5) | C55—C54—Ru3—C52 | −99.8 (6) |
C3—C2—Ru1—C15 | −80.2 (6) | C53—C54—Ru3—C51 | 64.5 (6) |
C11—C2—Ru1—C17 | −179.9 (5) | C55—C54—Ru3—C51 | −65.6 (5) |
C3—C2—Ru1—C17 | −9.8 (7) | C48—N3—Ru3—C38 | 18.2 (4) |
C11—C2—Ru1—C18 | −161.0 (5) | C48—N3—Ru3—C54 | −66.2 (5) |
C3—C2—Ru1—C18 | 9.1 (9) | C48—N3—Ru3—O3 | 99.7 (4) |
C11—C2—Ru1—C19 | 103.8 (18) | C48—N3—Ru3—C53 | −95.1 (5) |
C3—C2—Ru1—C19 | −86.1 (19) | C48—N3—Ru3—C55 | −64.6 (12) |
C1—O1—Ru1—C2 | 125.6 (5) | C48—N3—Ru3—C50 | −176.0 (5) |
C1—O1—Ru1—N1 | 46.1 (5) | C48—N3—Ru3—C52 | −132.1 (5) |
C1—O1—Ru1—C16 | −149.2 (5) | C48—N3—Ru3—C51 | −160.9 (5) |
C1—O1—Ru1—C14 | −40.6 (7) | C1—O3—Ru3—C38 | 103.6 (5) |
C1—O1—Ru1—C15 | −133.5 (11) | C1—O3—Ru3—C54 | −173.3 (5) |
C1—O1—Ru1—C17 | −125.9 (5) | C1—O3—Ru3—N3 | 25.5 (5) |
C1—O1—Ru1—C18 | −88.9 (5) | C1—O3—Ru3—C53 | −93.2 (12) |
C1—O1—Ru1—C19 | −55.9 (6) | C1—O3—Ru3—C55 | −158.7 (5) |
C12—N1—Ru1—C2 | 7.8 (5) | C1—O3—Ru3—C50 | −125.6 (6) |
C12—N1—Ru1—O1 | 88.5 (5) | C1—O3—Ru3—C52 | −72.8 (6) |
C12—N1—Ru1—C16 | −71.9 (7) | C1—O3—Ru3—C51 | −92.0 (6) |
C12—N1—Ru1—C14 | −126.0 (5) | C52—C53—Ru3—C38 | −170.8 (5) |
C12—N1—Ru1—C15 | −91.6 (5) | C54—C53—Ru3—C38 | 60.1 (6) |
C12—N1—Ru1—C18 | 174.7 (5) | C52—C53—Ru3—C54 | 129.0 (8) |
C12—N1—Ru1—C19 | −161.5 (5) | C52—C53—Ru3—N3 | −90.4 (6) |
C17—C16—Ru1—C2 | 119.6 (5) | C54—C53—Ru3—N3 | 140.6 (6) |
C15—C16—Ru1—C2 | −106.9 (5) | C52—C53—Ru3—O3 | 27.4 (14) |
C17—C16—Ru1—O1 | 40.3 (6) | C54—C53—Ru3—O3 | −101.7 (12) |
C15—C16—Ru1—O1 | 173.9 (4) | C52—C53—Ru3—C55 | 97.9 (6) |
C17—C16—Ru1—N1 | −165.4 (5) | C54—C53—Ru3—C55 | −31.1 (6) |
C15—C16—Ru1—N1 | −31.8 (7) | C52—C53—Ru3—C50 | 60.5 (6) |
C17—C16—Ru1—C14 | −104.1 (6) | C54—C53—Ru3—C50 | −68.6 (6) |
C15—C16—Ru1—C14 | 29.5 (5) | C54—C53—Ru3—C52 | −129.0 (8) |
C17—C16—Ru1—C15 | −133.6 (8) | C52—C53—Ru3—C51 | 26.1 (5) |
C15—C16—Ru1—C17 | 133.6 (8) | C54—C53—Ru3—C51 | −103.0 (6) |
C17—C16—Ru1—C18 | −30.2 (5) | C50—C55—Ru3—C38 | 148.3 (5) |
C15—C16—Ru1—C18 | 103.4 (6) | C54—C55—Ru3—C38 | −81.9 (5) |
C17—C16—Ru1—C19 | −67.7 (6) | C50—C55—Ru3—C54 | −129.7 (8) |
C15—C16—Ru1—C19 | 65.9 (6) | C50—C55—Ru3—N3 | −131.7 (11) |
C15—C14—Ru1—C2 | 41.7 (7) | C54—C55—Ru3—N3 | −2.0 (14) |
C19—C14—Ru1—C2 | 174.4 (5) | C50—C55—Ru3—O3 | 64.5 (6) |
C15—C14—Ru1—O1 | −157.1 (4) | C54—C55—Ru3—O3 | −165.8 (4) |
C19—C14—Ru1—O1 | −24.4 (8) | C50—C55—Ru3—C53 | −99.2 (6) |
C15—C14—Ru1—N1 | 118.3 (5) | C54—C55—Ru3—C53 | 30.5 (5) |
C19—C14—Ru1—N1 | −109.0 (5) | C54—C55—Ru3—C50 | 129.7 (8) |
C15—C14—Ru1—C16 | −29.5 (5) | C50—C55—Ru3—C52 | −62.0 (6) |
C19—C14—Ru1—C16 | 103.2 (6) | C54—C55—Ru3—C52 | 67.7 (5) |
C19—C14—Ru1—C15 | 132.7 (8) | C50—C55—Ru3—C51 | −28.1 (5) |
C15—C14—Ru1—C17 | −65.9 (6) | C54—C55—Ru3—C51 | 101.6 (5) |
C19—C14—Ru1—C17 | 66.7 (6) | C51—C50—Ru3—C38 | −174.5 (4) |
C15—C14—Ru1—C18 | −103.0 (6) | C55—C50—Ru3—C38 | −42.3 (7) |
C19—C14—Ru1—C18 | 29.7 (5) | C51—C50—Ru3—C54 | −100.6 (6) |
C15—C14—Ru1—C19 | −132.7 (8) | C55—C50—Ru3—C54 | 31.6 (6) |
C16—C15—Ru1—C2 | 78.0 (5) | C51—C50—Ru3—N3 | 23.6 (9) |
C14—C15—Ru1—C2 | −150.3 (5) | C55—C50—Ru3—N3 | 155.8 (6) |
C16—C15—Ru1—O1 | −20.2 (14) | C51—C50—Ru3—O3 | 108.8 (5) |
C14—C15—Ru1—O1 | 111.5 (12) | C55—C50—Ru3—O3 | −119.0 (6) |
C16—C15—Ru1—N1 | 160.3 (5) | C51—C50—Ru3—C53 | −62.2 (6) |
C14—C15—Ru1—N1 | −68.1 (5) | C55—C50—Ru3—C53 | 70.1 (6) |
C14—C15—Ru1—C16 | 131.7 (8) | C51—C50—Ru3—C55 | −132.2 (8) |
C16—C15—Ru1—C14 | −131.7 (8) | C51—C50—Ru3—C52 | −26.7 (5) |
C16—C15—Ru1—C17 | −28.2 (5) | C55—C50—Ru3—C52 | 105.5 (6) |
C14—C15—Ru1—C17 | 103.5 (6) | C55—C50—Ru3—C51 | 132.2 (8) |
C16—C15—Ru1—C18 | −65.7 (5) | C51—C52—Ru3—C38 | 152.0 (6) |
C14—C15—Ru1—C18 | 66.0 (6) | C53—C52—Ru3—C38 | 16.9 (10) |
C16—C15—Ru1—C19 | −103.1 (6) | C51—C52—Ru3—C54 | 103.5 (7) |
C14—C15—Ru1—C19 | 28.5 (5) | C53—C52—Ru3—C54 | −31.6 (6) |
C16—C17—Ru1—C2 | −67.2 (6) | C51—C52—Ru3—N3 | −130.6 (5) |
C18—C17—Ru1—C2 | 162.1 (5) | C53—C52—Ru3—N3 | 94.3 (6) |
C16—C17—Ru1—O1 | −149.6 (5) | C51—C52—Ru3—O3 | −35.2 (6) |
C18—C17—Ru1—O1 | 79.6 (6) | C53—C52—Ru3—O3 | −170.3 (5) |
C18—C17—Ru1—C16 | −130.7 (8) | C51—C52—Ru3—C53 | 135.1 (8) |
C16—C17—Ru1—C14 | 65.4 (6) | C51—C52—Ru3—C55 | 64.0 (6) |
C18—C17—Ru1—C14 | −65.4 (6) | C53—C52—Ru3—C55 | −71.1 (7) |
C16—C17—Ru1—C15 | 28.4 (5) | C51—C52—Ru3—C50 | 27.4 (5) |
C18—C17—Ru1—C15 | −102.3 (6) | C53—C52—Ru3—C50 | −107.7 (7) |
C16—C17—Ru1—C18 | 130.7 (8) | C53—C52—Ru3—C51 | −135.1 (8) |
C16—C17—Ru1—C19 | 101.7 (6) | C52—C51—Ru3—C38 | −118.4 (11) |
C18—C17—Ru1—C19 | −29.1 (6) | C50—C51—Ru3—C38 | 16.1 (14) |
C17—C18—Ru1—C2 | −29.9 (8) | C52—C51—Ru3—C54 | −65.9 (6) |
C19—C18—Ru1—C2 | −162.6 (5) | C50—C51—Ru3—C54 | 68.7 (6) |
C17—C18—Ru1—O1 | −103.5 (6) | C52—C51—Ru3—N3 | 58.0 (6) |
C19—C18—Ru1—O1 | 123.8 (5) | C50—C51—Ru3—N3 | −167.4 (5) |
C17—C18—Ru1—N1 | 172.6 (5) | C52—C51—Ru3—O3 | 152.6 (5) |
C19—C18—Ru1—N1 | 39.9 (7) | C50—C51—Ru3—O3 | −72.8 (5) |
C17—C18—Ru1—C16 | 29.8 (5) | C52—C51—Ru3—C53 | −27.7 (5) |
C19—C18—Ru1—C16 | −102.9 (6) | C50—C51—Ru3—C53 | 106.8 (6) |
C17—C18—Ru1—C14 | 103.8 (6) | C52—C51—Ru3—C55 | −105.1 (6) |
C19—C18—Ru1—C14 | −28.9 (5) | C50—C51—Ru3—C55 | 29.5 (6) |
C17—C18—Ru1—C15 | 66.8 (6) | C52—C51—Ru3—C50 | −134.5 (8) |
C19—C18—Ru1—C15 | −65.9 (5) | C50—C51—Ru3—C52 | 134.5 (8) |
C19—C18—Ru1—C17 | −132.7 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···F6i | 0.92 | 2.37 | 3.245 (7) | 159 |
N1—H1B···O3 | 0.92 | 2.09 | 2.860 (7) | 141 |
N2—H2B···O1 | 0.92 | 2.38 | 2.967 (7) | 122 |
N3—H3A···F4ii | 0.92 | 2.36 | 3.202 (8) | 153 |
N3—H3B···O2 | 0.92 | 1.92 | 2.739 (7) | 148 |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | [Ru3(C12H12N)3(CO3)(C6H6)3]PF6·CH2Cl2 |
Mr | 1338.12 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 173 |
a, b, c (Å) | 11.4732 (2), 19.1377 (5), 12.0169 (2) |
β (°) | 90.832 (2) |
V (Å3) | 2638.28 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.05 |
Crystal size (mm) | 0.12 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15434, 12813, 9862 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.132, 1.06 |
No. of reflections | 12813 |
No. of parameters | 670 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.74, −0.99 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.01 (3) |
Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···F6i | 0.92 | 2.37 | 3.245 (7) | 159.0 |
N1—H1B···O3 | 0.92 | 2.09 | 2.860 (7) | 140.9 |
N2—H2B···O1 | 0.92 | 2.38 | 2.967 (7) | 121.6 |
N3—H3A···F4ii | 0.92 | 2.36 | 3.202 (8) | 152.5 |
N3—H3B···O2 | 0.92 | 1.92 | 2.739 (7) | 147.8 |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) x, y, z−1. |
Acknowledgements
The authors thank André De Cian for his contribution to this work, and the CNRS for financial support. The authors are also indebted to the Ministère de l'Education Nationale for a fellowship granted to JBS.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Chiral cycloruthenated half-sandwich complexes have recently experienced a renewed interest because of their catalytic properties applied to asymmetric synthesis (Sortais et al., 2006). Single crystals of the title compound (I) have been obtained while attempting to isolate catalytic intermediates.
The molecular structure of the compound (I) (Fig. 1) consists of a trinuclear cation comprising three pseudotetrahedral ruthenium (II) centres, which are each coordinated by a bridging µ3-carbonato ligand, a η6-benzene ligand and a cyclometallated (R)-(+)-1-(1-naphthyl)ethylamine, together with a non-coordinating hexafluorophosphate anion and one molecule of methylene chloride. The complex crystallizes in the P21 chiral space group, which confirms the presence of a single enantiomer. A partial view showing the coordination sphere of one of the ruthenium atoms is represented Fig. 2, the two others are similar. Its structure is closely related to that of the reported parent complex bearing dimethylphenylphosphine instead of the carbonato ligand (Sortais et al., 2007): SRu configuration, δ conformation of the metallacycle, axial position of the methyl group. The ruthenium atoms and the four atoms belonging to the carbonato are coplanar, the sum of the three Ru···Ccarbonato···Ru angles reaching 359.89°. The three ruthenium atoms form a nearly equilateral triangle with Ru···Ru distances within the 5.2–5.5 Å range. The benzene ligands lie on one side of the corresponding plane and the cycloruthenated on the other side.
A search in the Cambridge Database revealed no previously reported crystal structure of a carbonato-bridged chemically C3-symmetric trinuclear ruthenium complex. Related polynuclear carbonato ruthenium complexes where each oxygen atom is ligated to at least one ruthenium atom exhibit metal-metal bonds (Cotton et al., 1992; Lindsay et al., 1987; Maurette et al., 1999). Interestingly, a closely related monomeric half-sandwich complex where a carbonato ligand chelates the Ru center has been recently reported (Demerseman et al., 2006); we notice that in complex (I) the Ru—O bond distances are longer (2.118 (4)–2.132 (4) Å), probably because of steric repulsions.