The title compound, [RuCl2(C10H14)(C21H21O3P)] crystallizes with two independent complex molecules in the asymmetric unit. In the crystal, weak C—H⋯Cl/O/π interactions are observed.
Keywords: crystal structure, ruthenium, p-cymene, organometallic
Abstract
The title compound, [RuCl2(C10H14)(C21H21O3P)], crystallizes with two complex molecules in the asymmetric unit. The RuII atom has a classical three-legged piano-stool environment being coordinated by a cymene ligand [Ru—centroid = 1.707 (2)/1.704 (2) Å], a tris(4-methoxyphenyl)phosphane ligand [Ru—P = 2.3629 (15)/2.3665 (15) Å] and two chloride atoms with the Ru—Cl bonds adopting two distinct values of 2.4068 (16)/2.4167 (16) and 2.4016 (15)/2.4244 (16) Å. The effective cone and solid angles for the phosphane ligands were calculated to be 149.5/150.2° and 25.3/25.6°, respectively. In the crystal, weak C—H⋯Cl/O/π interactions are observed. The crystal was refined as a two-component twin.
Structure description
The activity of the half-sandwich RuII–arene complexes is well known in the catalytic transfer hydrogenation of carbonyl compounds (Chen et al., 2002 ▸; Crochet et al., 2003 ▸; Aydemir et al., 2011 ▸; Wang et al., 2011 ▸). Reported here is the η6-cymene–Ru complex containing the phosphane, P(C6H4OMe-p)3, as part of ongoing structural investigations into these type of complexes.
The title compound crystallizes in the triclinic space group P
(Z = 4), with its two unique molecules adopting a distorted pseudo-octahedral arrangement, revealing the typical three-legged piano-stool geometry. The coordination sphere of the ruthenium is occupied by a cymene, a tris(4-methoxyphenyl)phosphane and two chloride atoms (see Fig. 1 ▸). The distances between Ru and the centroid of the π-bonded η6-cymene ligand are 1.707 (2) and 1.704 (2) Å for the two independent molecules; the mean Ru—C bond lengths are 2.217 (6) and 2.214 (6) Å. The coordination of the remaining ligands to the Ru atom shows a slight deviation from the typical octahedral geometry with Cl—Ru—Cl = 88.47 (6) and 88.77 (6)°, respectively; Cl—Ru—P = 86.50 (5)/88.03 (5) and 86.05 (5)/88.21 (6)°. The Ru—P bond lengths are 2.3629 (15) and 2.3665 (15) Å, while the Ru—Cl bonds adopt two distinct values of 2.4068 (16)/2.4167 (16) and 2.4016 (15)/2.4244 (16) Å for Ru1 and Ru2, respectively. The above bond lengths are within normal ranges as data extracted from the Cambridge Structural Database (Allen, 2002 ▸) for (η6-aryl)RuCl2(PR
3) systems from 429 hits, containing 535 usable Ru—Cl observations, show a mean value of 2.412 (12) Å in a range from 2.378 to 2.459 Å. The same group of structures show for the Ru—P distance a mean value of 2.34 (3) Å in a range from 2.235 to 2.434 Å. The geometries of the two independent molecules are virtually identical, as seen from a superimposed fit with an r.m.s. deviation of 0.0525 Å (Macrae et al., 2020 ▸; Weng, Motherwell, Allen et al., 2008 ▸; Weng, Motherwell & Cole, 2008 ▸) (see Fig. 2 ▸).
Figure 1.
(a) and (b): Views of the title complex showing the atom-numbering scheme for the two independent molecules in the asymmetric unit and 50% probability displacement ellipsoids. Molecules were rotated independently to obtain the best view for each.
Figure 2.
An overlay diagram showing the conformational similarity between the two molecules in the asymmetric unit (r.m.s.d. = 0.0525 Å).
To describe the steric demand of phosphane ligands, we have implemented the two most widely used models, i.e. the solid angle (a percentage projection of the ligand onto a sphere; Immirzi & Musco, 1977 ▸) and the crystallographic cone angle (an adaptation from the Tolman cone angle model; Tolman, 1977 ▸), where the orientation of the substituents are taken from crystallographic data instead of a CPK model, and the Ru—P bond length adjusted to 2.28 Å to normalize any influence this variation may have on the cone size (Müller & Mingos, 1995 ▸) to calculate an effective cone angle (Otto, 2001 ▸). The effective cone angle values obtained with this method for the two independent molecules in the asymmetric unit are 149.5 and 150.2° compared to the Tolman cone angle of 145.0° obtained from the QALE website (Fernandez et al., 2003 ▸). The solid angles, utilizing SOLID-G (Guzei & Wendt, 2004 ▸) were calculated as 25.35 and 25.61°. It is interesting to note that despite these similar geometric values, the phosphane ligands of these two independent molecules show a marked variation in their orientations of substituents as the P1-phosphane has a C—H⋯π interaction between two of its substituents, whereas the P2-phosphane does not show this feature. The rest of the crystal displays an array of weak C–H⋯Cl/O interactions (see Fig. 3 ▸, Table 1 ▸ for a summary of interactions).
Figure 3.
(a) and (b): Partial packing diagrams showing the C—H⋯Cl/O/π interactions (indicated by blue dashed lines). H atoms not involved in interactions are omitted for clarity.
Table 1. Hydrogen-bond geometry (Å, °).
Cg1 is the centroid of the C1–C6 ring.
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
---|---|---|---|---|
C5—H5⋯Cl2i | 0.95 | 2.62 | 3.566 (7) | 171 |
C36—H36⋯Cl4ii | 0.95 | 2.6 | 3.506 (7) | 159 |
C43—H43⋯Cl1iii | 0.95 | 2.78 | 3.619 (7) | 147 |
C62—H62B⋯O5iii | 0.98 | 2.58 | 3.362 (9) | 136 |
C18—H18⋯Cl2 | 0.95 | 2.8 | 3.643 (7) | 149 |
C24—H24⋯Cl1 | 0.95 | 2.62 | 3.427 (6) | 143 |
C49—H49⋯Cl3 | 0.95 | 2.61 | 3.416 (6) | 143 |
C55—H55⋯Cl4 | 0.95 | 2.71 | 3.562 (6) | 149 |
C20—H20⋯Cg1 | 0.95 | 2.95 | 3.614 (7) | 128 |
Symmetry codes: (i)
; (ii)
; (iii)
.
Synthesis and crystallization
A solution of P(C6H4OMe-p)3 (62.7 mg, 0.178 mmol) in CH2Cl2 (10 ml) was added to a stirred orange solution of [Ru(p-cymene)Cl2]2 (50 mg, 0.081 mmol) under Ar in the same solvent (15 ml) and stirred at r.t. for 24 h. The resulting red reaction mixture was filtered, the filtrate concentrated under reduced pressure to ca 5 ml. Cold diethyl ether (10 ml) was carefully added and the solvent left to slowly evaporate whereby a sample of [RuCl2(C10H14)(C21H21O3P)] suitable for single-crystal X-ray diffraction was obtained as orange crystals.
Analytical data: 31P{1H} NMR (CDCl3, 161.99 MHz): δ (p.p.m.) 21.39 (s). 1H NMR (CDCl3, 400 MHz): δ (p.p.m.) 1.11 (d, 6H, 2 × CH3 of isopropyl); 1.84 (s, 3H, CH3 of cymene); 2.87 (m, 1H, CH of isopropyl); 3.78 (s, 9H, 3 × CH3 of OMe); 4.93 (d, 2H, Ar—H of cymene); 5.20 (d, 2H, Ar—H of cymene); 6.85 (dd, 6H, Ar—H of C6H4OMe-p); 7.69 (t, 6H, Ar—H of C6H4OMe-p).
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The deepest residual electron-density hole (−1.94 e Å−3) is located at 0.59 Å from Ru1 and the highest peak (3.95 e Å−3) 0.90 Å from Ru1. Initial refinement of data indicated a two-component twin with a 180° rotation about the [100] reciprocal direction. Refinement with the appropriate twin law yields a batch scaling factor of 0.18.
Table 2. Experimental details.
Crystal data | |
Chemical formula | [RuCl2(C10H14)(C21H21O3P)] |
M r | 658.53 |
Crystal system, space group | Triclinic, P
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Temperature (K) | 100 |
a, b, c (Å) | 12.4069 (17), 14.0221 (19), 16.934 (2) |
α, β, γ (°) | 91.459 (3), 91.205 (3), 90.613 (3) |
V (Å3) | 2944.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
μ (mm−1) | 0.80 |
Crystal size (mm) | 0.58 × 0.28 × 0.21 |
Data collection | |
Diffractometer | Bruker APEX DUO 4K-CCD |
Absorption correction | Multi-scan SADABS (Bruker, 2008 ▸) |
T min, T max | 0.654, 0.850 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 88599, 14838, 13368 |
R int | 0.053 |
(sin θ/λ)max (Å−1) | 0.674 |
Refinement | |
R[F 2 > 2σ(F 2)], wR(F 2), S | 0.070, 0.181, 1.09 |
No. of reflections | 14838 |
No. of parameters | 698 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 3.95, −1.95 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2414314621012591/tk4072sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314621012591/tk4072Isup2.hkl
CCDC reference: 2124507
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
Financial assistance from the Research Fund of the University of Johannesburg is gratefully acknowledged.
full crystallographic data
Crystal data
[RuCl2(C10H14)(C21H21O3P)] | Z = 4 |
Mr = 658.53 | F(000) = 1352 |
Triclinic, P1 | Dx = 1.486 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.4069 (17) Å | Cell parameters from 9270 reflections |
b = 14.0221 (19) Å | θ = 2.6–28.5° |
c = 16.934 (2) Å | µ = 0.80 mm−1 |
α = 91.459 (3)° | T = 100 K |
β = 91.205 (3)° | Block, orange |
γ = 90.613 (3)° | 0.58 × 0.28 × 0.21 mm |
V = 2944.2 (7) Å3 |
Data collection
Bruker APEX DUO 4K-CCD diffractometer | 14838 independent reflections |
Graphite monochromator | 13368 reflections with I > 2σ(I) |
Detector resolution: 8.4 pixels mm-1 | Rint = 0.053 |
φ and ω scans | θmax = 28.6°, θmin = 1.2° |
Absorption correction: multi-scan SADABS (Bruker, 2008) | h = −16→16 |
Tmin = 0.654, Tmax = 0.850 | k = −18→18 |
88599 measured reflections | l = −22→22 |
Refinement
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)] = 0.070 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0475P)2 + 35.9275P] where P = (Fo2 + 2Fc2)/3 |
14838 reflections | (Δ/σ)max = 0.047 |
698 parameters | Δρmax = 3.95 e Å−3 |
0 restraints | Δρmin = −1.94 e Å−3 |
Special details
Experimental. The intensity data was collected on a Bruker Apex DUO 4 K-CCD diffractometer using an exposure time of 10 s/frame. A total of 3975 frames were collected with a frame width of 0.5° covering up to θ = 28.62° with 98.4% completeness accomplished. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.The aromatic-, methine- and methyl-H atoms were placed in geometrically idealized positions with C—H = 0.95, 1.00, and 0.98 Å, respectively, and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(C) for methyl-H and Uiso(H) = 1.2Ueq(C) for aromatic- and methine-H atoms. Methyl torsion angles were refined from electron density. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x | y | z | Uiso*/Ueq | ||
C1 | 0.9475 (5) | 0.2043 (4) | 0.3616 (4) | 0.0200 (12) | |
C2 | 0.8727 (5) | 0.2354 (4) | 0.3038 (4) | 0.0182 (11) | |
H2 | 0.8617 | 0.1993 | 0.256 | 0.022* | |
C3 | 0.8146 (5) | 0.3197 (4) | 0.3169 (4) | 0.0223 (13) | |
H3 | 0.7666 | 0.3407 | 0.2766 | 0.027* | |
C4 | 0.8250 (5) | 0.3741 (4) | 0.3878 (4) | 0.0228 (13) | |
C5 | 0.8988 (5) | 0.3408 (4) | 0.4470 (4) | 0.0211 (12) | |
H5 | 0.908 | 0.376 | 0.4954 | 0.025* | |
C6 | 0.9574 (5) | 0.2576 (4) | 0.4346 (4) | 0.0205 (12) | |
H6 | 1.0045 | 0.2361 | 0.4752 | 0.025* | |
C7 | 1.0125 (5) | 0.3287 (4) | 0.1271 (3) | 0.0172 (11) | |
C8 | 1.1043 (5) | 0.3261 (4) | 0.0816 (4) | 0.0222 (12) | |
H8 | 1.1598 | 0.3723 | 0.0913 | 0.027* | |
C9 | 1.1166 (6) | 0.2571 (5) | 0.0220 (4) | 0.0274 (14) | |
H9 | 1.1793 | 0.2574 | −0.0092 | 0.033* | |
C10 | 1.0370 (6) | 0.1878 (5) | 0.0083 (4) | 0.0271 (14) | |
C11 | 0.9439 (6) | 0.1888 (5) | 0.0538 (4) | 0.0260 (14) | |
H11 | 0.8895 | 0.1413 | 0.0451 | 0.031* | |
C12 | 0.9318 (5) | 0.2589 (5) | 0.1109 (4) | 0.0219 (12) | |
H12 | 0.8674 | 0.2604 | 0.1402 | 0.026* | |
C13 | 0.8761 (5) | 0.4836 (4) | 0.1781 (4) | 0.0186 (11) | |
C14 | 0.8191 (5) | 0.4697 (4) | 0.1067 (4) | 0.0210 (12) | |
H14 | 0.8367 | 0.418 | 0.0722 | 0.025* | |
C15 | 0.7368 (6) | 0.5309 (5) | 0.0856 (4) | 0.0258 (13) | |
H15 | 0.6986 | 0.5211 | 0.0368 | 0.031* | |
C16 | 0.7102 (5) | 0.6067 (4) | 0.1358 (4) | 0.0240 (13) | |
C17 | 0.7668 (5) | 0.6216 (4) | 0.2071 (4) | 0.0238 (13) | |
H17 | 0.7493 | 0.6736 | 0.2413 | 0.029* | |
C18 | 0.8488 (5) | 0.5601 (5) | 0.2276 (4) | 0.0226 (12) | |
H18 | 0.8871 | 0.5703 | 0.2763 | 0.027* | |
C19 | 1.0993 (5) | 0.5078 (4) | 0.1843 (4) | 0.0203 (12) | |
C20 | 1.0782 (5) | 0.5693 (5) | 0.1217 (4) | 0.0232 (13) | |
H20 | 1.0116 | 0.5632 | 0.0933 | 0.028* | |
C21 | 1.1521 (5) | 0.6388 (4) | 0.1003 (4) | 0.0222 (12) | |
H21 | 1.1359 | 0.6796 | 0.0579 | 0.027* | |
C22 | 1.2496 (5) | 0.6478 (4) | 0.1415 (4) | 0.0215 (12) | |
C23 | 1.2724 (5) | 0.5878 (5) | 0.2036 (4) | 0.0230 (13) | |
H23 | 1.3393 | 0.5941 | 0.2317 | 0.028* | |
C24 | 1.1978 (5) | 0.5184 (5) | 0.2251 (4) | 0.0231 (12) | |
H24 | 1.2141 | 0.478 | 0.2679 | 0.028* | |
C25 | 0.7616 (6) | 0.4622 (5) | 0.4029 (5) | 0.0322 (16) | |
H25A | 0.7462 | 0.4932 | 0.3527 | 0.048* | |
H25B | 0.8032 | 0.506 | 0.438 | 0.048* | |
H25C | 0.6936 | 0.4453 | 0.4278 | 0.048* | |
C26 | 1.0125 (5) | 0.1142 (4) | 0.3513 (4) | 0.0207 (12) | |
H26 | 1.0865 | 0.1269 | 0.3739 | 0.025* | |
C27 | 0.9588 (6) | 0.0383 (5) | 0.4007 (4) | 0.0280 (14) | |
H27A | 0.9638 | 0.0577 | 0.4567 | 0.042* | |
H27B | 0.9954 | −0.0227 | 0.3927 | 0.042* | |
H27C | 0.8828 | 0.0312 | 0.3844 | 0.042* | |
C28 | 1.0233 (6) | 0.0813 (5) | 0.2656 (4) | 0.0278 (14) | |
H28A | 0.9523 | 0.0624 | 0.2437 | 0.042* | |
H28B | 1.0719 | 0.0268 | 0.2628 | 0.042* | |
H28C | 1.0528 | 0.1336 | 0.235 | 0.042* | |
C29 | 1.1271 (9) | 0.1161 (7) | −0.0998 (5) | 0.049 (2) | |
H29A | 1.1253 | 0.1741 | −0.1309 | 0.073* | |
H29B | 1.1218 | 0.06 | −0.1354 | 0.073* | |
H29C | 1.1949 | 0.1144 | −0.0692 | 0.073* | |
C30 | 0.5940 (7) | 0.7367 (5) | 0.1615 (6) | 0.0390 (19) | |
H30A | 0.5683 | 0.7091 | 0.2103 | 0.058* | |
H30B | 0.5354 | 0.7718 | 0.1362 | 0.058* | |
H30C | 0.6545 | 0.7804 | 0.1739 | 0.058* | |
C31 | 1.3045 (6) | 0.7780 (5) | 0.0639 (5) | 0.0304 (15) | |
H31A | 1.2944 | 0.7418 | 0.014 | 0.046* | |
H31B | 1.3646 | 0.8233 | 0.0594 | 0.046* | |
H31C | 1.2385 | 0.813 | 0.0757 | 0.046* | |
C32 | 0.4449 (5) | 0.2814 (4) | 0.1359 (4) | 0.0190 (12) | |
C33 | 0.3718 (5) | 0.2540 (4) | 0.1934 (4) | 0.0183 (11) | |
H33 | 0.3641 | 0.292 | 0.2402 | 0.022* | |
C34 | 0.3089 (5) | 0.1683 (4) | 0.1812 (4) | 0.0210 (12) | |
H34 | 0.2632 | 0.148 | 0.2221 | 0.025* | |
C35 | 0.3126 (5) | 0.1135 (4) | 0.1110 (4) | 0.0212 (12) | |
C36 | 0.3841 (5) | 0.1456 (5) | 0.0516 (4) | 0.0226 (12) | |
H36 | 0.3881 | 0.1106 | 0.003 | 0.027* | |
C37 | 0.4476 (5) | 0.2269 (5) | 0.0639 (4) | 0.0214 (12) | |
H37 | 0.494 | 0.2467 | 0.0233 | 0.026* | |
C38 | 0.5152 (5) | 0.1593 (4) | 0.3719 (3) | 0.0185 (11) | |
C39 | 0.6095 (6) | 0.1654 (5) | 0.4173 (4) | 0.0250 (13) | |
H39 | 0.6641 | 0.1195 | 0.4087 | 0.03* | |
C40 | 0.6268 (6) | 0.2363 (5) | 0.4749 (4) | 0.0281 (14) | |
H40 | 0.6913 | 0.2376 | 0.5062 | 0.034* | |
C41 | 0.5486 (7) | 0.3059 (5) | 0.4864 (4) | 0.0299 (15) | |
C42 | 0.4540 (6) | 0.3013 (5) | 0.4414 (4) | 0.0280 (14) | |
H42 | 0.4006 | 0.3485 | 0.4492 | 0.034* | |
C43 | 0.4362 (5) | 0.2290 (4) | 0.3853 (3) | 0.0214 (12) | |
H43 | 0.3703 | 0.2263 | 0.3557 | 0.026* | |
C44 | 0.5937 (5) | −0.0197 (4) | 0.3173 (4) | 0.0189 (11) | |
C45 | 0.5752 (5) | −0.0781 (5) | 0.3822 (4) | 0.0228 (13) | |
H45 | 0.5114 | −0.0699 | 0.4116 | 0.027* | |
C46 | 0.6487 (5) | −0.1481 (5) | 0.4044 (4) | 0.0235 (13) | |
H46 | 0.6348 | −0.1869 | 0.4483 | 0.028* | |
C47 | 0.7417 (5) | −0.1600 (4) | 0.3618 (4) | 0.0220 (12) | |
C48 | 0.7613 (5) | −0.1022 (5) | 0.2979 (4) | 0.0238 (13) | |
H48 | 0.8256 | −0.1102 | 0.2692 | 0.029* | |
C49 | 0.6883 (5) | −0.0329 (4) | 0.2755 (4) | 0.0209 (12) | |
H49 | 0.7029 | 0.0057 | 0.2316 | 0.025* | |
C50 | 0.3715 (5) | 0.0036 (4) | 0.3202 (4) | 0.0200 (12) | |
C51 | 0.3168 (5) | 0.0175 (5) | 0.3909 (4) | 0.0221 (12) | |
H51 | 0.3372 | 0.0691 | 0.4257 | 0.027* | |
C52 | 0.2334 (5) | −0.0431 (5) | 0.4106 (4) | 0.0255 (13) | |
H52 | 0.1972 | −0.0331 | 0.4589 | 0.031* | |
C53 | 0.2024 (5) | −0.1183 (5) | 0.3603 (4) | 0.0252 (14) | |
C54 | 0.2562 (5) | −0.1337 (4) | 0.2897 (4) | 0.0236 (13) | |
H54 | 0.2357 | −0.1855 | 0.2551 | 0.028* | |
C55 | 0.3400 (5) | −0.0729 (5) | 0.2706 (4) | 0.0226 (12) | |
H55 | 0.3767 | −0.0836 | 0.2225 | 0.027* | |
C56 | 0.2434 (6) | 0.0267 (5) | 0.0959 (5) | 0.0296 (15) | |
H56A | 0.2352 | −0.0074 | 0.1452 | 0.044* | |
H56B | 0.2772 | −0.0151 | 0.0566 | 0.044* | |
H56C | 0.1723 | 0.0459 | 0.0759 | 0.044* | |
C57 | 0.5140 (6) | 0.3707 (4) | 0.1460 (4) | 0.0242 (13) | |
H57 | 0.5865 | 0.3565 | 0.1241 | 0.029* | |
C58 | 0.4621 (6) | 0.4480 (5) | 0.0951 (4) | 0.0269 (14) | |
H58A | 0.4603 | 0.4265 | 0.0396 | 0.04* | |
H58B | 0.5046 | 0.5072 | 0.1009 | 0.04* | |
H58C | 0.3884 | 0.4595 | 0.1126 | 0.04* | |
C59 | 0.5305 (6) | 0.4050 (5) | 0.2319 (4) | 0.0297 (15) | |
H59A | 0.4615 | 0.4258 | 0.2531 | 0.045* | |
H59B | 0.5821 | 0.4584 | 0.2344 | 0.045* | |
H59C | 0.5585 | 0.3526 | 0.2633 | 0.045* | |
C60 | 0.6452 (9) | 0.3841 (7) | 0.5933 (6) | 0.053 (2) | |
H60A | 0.6483 | 0.3251 | 0.6231 | 0.079* | |
H60B | 0.6376 | 0.4386 | 0.63 | 0.079* | |
H60C | 0.7117 | 0.3915 | 0.5637 | 0.079* | |
C61 | 0.7966 (6) | −0.2890 (5) | 0.4415 (5) | 0.0300 (15) | |
H61A | 0.7958 | −0.2524 | 0.4916 | 0.045* | |
H61B | 0.8528 | −0.3374 | 0.4442 | 0.045* | |
H61C | 0.7263 | −0.3202 | 0.432 | 0.045* | |
C62 | 0.0789 (7) | −0.2475 (5) | 0.3309 (6) | 0.041 (2) | |
H62A | 0.0605 | −0.2194 | 0.28 | 0.062* | |
H62B | 0.0144 | −0.277 | 0.3526 | 0.062* | |
H62C | 0.1342 | −0.2961 | 0.3233 | 0.062* | |
P1 | 0.99715 (12) | 0.41789 (10) | 0.20650 (9) | 0.0166 (3) | |
P2 | 0.49275 (13) | 0.06929 (10) | 0.29344 (9) | 0.0169 (3) | |
Cl1 | 1.17183 (12) | 0.30968 (11) | 0.32444 (10) | 0.0246 (3) | |
Cl2 | 1.04584 (14) | 0.50981 (11) | 0.38312 (9) | 0.0242 (3) | |
Cl3 | 0.66582 (12) | 0.17348 (11) | 0.17376 (10) | 0.0254 (3) | |
Cl4 | 0.52593 (13) | −0.02586 (10) | 0.11852 (8) | 0.0211 (3) | |
Ru1 | 0.98521 (4) | 0.35528 (3) | 0.33430 (3) | 0.01596 (11) | |
Ru2 | 0.47608 (4) | 0.13050 (3) | 0.16486 (3) | 0.01558 (11) | |
O1 | 1.0393 (5) | 0.1160 (4) | −0.0478 (3) | 0.0378 (13) | |
O2 | 0.6284 (4) | 0.6629 (3) | 0.1096 (3) | 0.0314 (11) | |
O3 | 1.3276 (4) | 0.7138 (3) | 0.1262 (3) | 0.0269 (10) | |
O4 | 0.5567 (6) | 0.3797 (4) | 0.5406 (3) | 0.0430 (14) | |
O5 | 0.8184 (4) | −0.2262 (3) | 0.3785 (3) | 0.0266 (10) | |
O6 | 0.1193 (4) | −0.1746 (3) | 0.3846 (3) | 0.0321 (12) |
Atomic displacement parameters (Å2)
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.022 (3) | 0.012 (2) | 0.027 (3) | 0.000 (2) | 0.002 (2) | 0.010 (2) |
C2 | 0.018 (3) | 0.016 (3) | 0.021 (3) | −0.002 (2) | −0.003 (2) | 0.004 (2) |
C3 | 0.023 (3) | 0.015 (3) | 0.029 (3) | −0.002 (2) | 0.002 (2) | 0.011 (2) |
C4 | 0.021 (3) | 0.016 (3) | 0.032 (3) | 0.001 (2) | 0.010 (3) | 0.006 (2) |
C5 | 0.026 (3) | 0.020 (3) | 0.017 (3) | −0.003 (2) | 0.005 (2) | 0.003 (2) |
C6 | 0.021 (3) | 0.021 (3) | 0.020 (3) | 0.004 (2) | 0.003 (2) | 0.010 (2) |
C7 | 0.023 (3) | 0.012 (2) | 0.017 (3) | 0.003 (2) | −0.001 (2) | 0.0039 (19) |
C8 | 0.023 (3) | 0.019 (3) | 0.025 (3) | 0.002 (2) | 0.001 (2) | 0.009 (2) |
C9 | 0.035 (4) | 0.025 (3) | 0.023 (3) | 0.004 (3) | 0.002 (3) | 0.007 (3) |
C10 | 0.041 (4) | 0.022 (3) | 0.018 (3) | 0.005 (3) | −0.002 (3) | 0.003 (2) |
C11 | 0.032 (4) | 0.022 (3) | 0.024 (3) | −0.003 (3) | −0.006 (3) | 0.009 (2) |
C12 | 0.023 (3) | 0.023 (3) | 0.020 (3) | −0.002 (2) | −0.004 (2) | 0.008 (2) |
C13 | 0.018 (3) | 0.017 (3) | 0.020 (3) | −0.002 (2) | 0.000 (2) | 0.007 (2) |
C14 | 0.023 (3) | 0.019 (3) | 0.022 (3) | 0.000 (2) | −0.001 (2) | 0.005 (2) |
C15 | 0.027 (3) | 0.026 (3) | 0.025 (3) | 0.002 (3) | −0.006 (3) | 0.006 (3) |
C16 | 0.020 (3) | 0.017 (3) | 0.036 (4) | −0.003 (2) | −0.004 (3) | 0.011 (2) |
C17 | 0.027 (3) | 0.015 (3) | 0.029 (3) | −0.001 (2) | 0.001 (3) | 0.003 (2) |
C18 | 0.023 (3) | 0.020 (3) | 0.024 (3) | −0.001 (2) | −0.003 (2) | 0.005 (2) |
C19 | 0.020 (3) | 0.020 (3) | 0.022 (3) | −0.001 (2) | 0.004 (2) | 0.005 (2) |
C20 | 0.022 (3) | 0.023 (3) | 0.025 (3) | −0.004 (2) | −0.003 (2) | 0.006 (2) |
C21 | 0.024 (3) | 0.018 (3) | 0.026 (3) | −0.004 (2) | −0.001 (2) | 0.009 (2) |
C22 | 0.022 (3) | 0.017 (3) | 0.026 (3) | −0.002 (2) | 0.001 (2) | 0.003 (2) |
C23 | 0.019 (3) | 0.020 (3) | 0.030 (3) | −0.001 (2) | −0.002 (2) | 0.010 (2) |
C24 | 0.024 (3) | 0.021 (3) | 0.025 (3) | 0.000 (2) | −0.001 (2) | 0.007 (2) |
C25 | 0.036 (4) | 0.019 (3) | 0.042 (4) | 0.007 (3) | 0.014 (3) | 0.006 (3) |
C26 | 0.022 (3) | 0.017 (3) | 0.024 (3) | 0.004 (2) | 0.000 (2) | 0.005 (2) |
C27 | 0.030 (3) | 0.019 (3) | 0.035 (4) | 0.005 (3) | 0.002 (3) | 0.012 (3) |
C28 | 0.036 (4) | 0.019 (3) | 0.029 (3) | 0.007 (3) | 0.005 (3) | 0.005 (2) |
C29 | 0.076 (7) | 0.038 (4) | 0.033 (4) | −0.003 (4) | 0.015 (4) | −0.006 (3) |
C30 | 0.031 (4) | 0.026 (4) | 0.060 (5) | 0.007 (3) | −0.015 (4) | 0.001 (3) |
C31 | 0.027 (3) | 0.021 (3) | 0.044 (4) | −0.003 (3) | 0.002 (3) | 0.014 (3) |
C32 | 0.018 (3) | 0.015 (3) | 0.025 (3) | 0.003 (2) | −0.001 (2) | 0.012 (2) |
C33 | 0.020 (3) | 0.010 (2) | 0.026 (3) | 0.007 (2) | 0.003 (2) | 0.007 (2) |
C34 | 0.021 (3) | 0.013 (3) | 0.030 (3) | 0.000 (2) | 0.003 (2) | 0.012 (2) |
C35 | 0.021 (3) | 0.018 (3) | 0.025 (3) | 0.000 (2) | −0.004 (2) | 0.006 (2) |
C36 | 0.023 (3) | 0.025 (3) | 0.020 (3) | 0.007 (2) | −0.004 (2) | 0.002 (2) |
C37 | 0.020 (3) | 0.025 (3) | 0.020 (3) | 0.005 (2) | −0.001 (2) | 0.011 (2) |
C38 | 0.023 (3) | 0.016 (2) | 0.018 (3) | −0.001 (2) | 0.003 (2) | 0.006 (2) |
C39 | 0.025 (3) | 0.027 (3) | 0.023 (3) | 0.001 (3) | 0.001 (2) | 0.007 (2) |
C40 | 0.033 (4) | 0.027 (3) | 0.024 (3) | −0.008 (3) | −0.003 (3) | 0.010 (3) |
C41 | 0.049 (4) | 0.020 (3) | 0.021 (3) | −0.005 (3) | 0.007 (3) | 0.006 (2) |
C42 | 0.041 (4) | 0.018 (3) | 0.026 (3) | 0.000 (3) | 0.009 (3) | 0.010 (2) |
C43 | 0.029 (3) | 0.021 (3) | 0.014 (3) | 0.004 (2) | 0.002 (2) | 0.007 (2) |
C44 | 0.022 (3) | 0.017 (3) | 0.018 (3) | 0.001 (2) | 0.000 (2) | 0.007 (2) |
C45 | 0.025 (3) | 0.021 (3) | 0.023 (3) | 0.006 (2) | 0.005 (2) | 0.012 (2) |
C46 | 0.026 (3) | 0.020 (3) | 0.025 (3) | 0.003 (2) | 0.003 (2) | 0.011 (2) |
C47 | 0.022 (3) | 0.017 (3) | 0.027 (3) | 0.004 (2) | −0.002 (2) | 0.004 (2) |
C48 | 0.022 (3) | 0.022 (3) | 0.028 (3) | 0.004 (2) | 0.003 (2) | 0.004 (2) |
C49 | 0.022 (3) | 0.020 (3) | 0.021 (3) | 0.002 (2) | 0.000 (2) | 0.008 (2) |
C50 | 0.016 (3) | 0.021 (3) | 0.023 (3) | 0.003 (2) | 0.002 (2) | 0.010 (2) |
C51 | 0.021 (3) | 0.022 (3) | 0.024 (3) | 0.003 (2) | 0.001 (2) | 0.008 (2) |
C52 | 0.025 (3) | 0.027 (3) | 0.026 (3) | 0.002 (3) | 0.007 (3) | 0.011 (3) |
C53 | 0.020 (3) | 0.022 (3) | 0.035 (4) | 0.005 (2) | 0.007 (3) | 0.015 (3) |
C54 | 0.023 (3) | 0.016 (3) | 0.032 (3) | 0.002 (2) | 0.003 (3) | 0.006 (2) |
C55 | 0.023 (3) | 0.022 (3) | 0.024 (3) | 0.002 (2) | 0.004 (2) | 0.006 (2) |
C56 | 0.028 (3) | 0.021 (3) | 0.039 (4) | 0.000 (3) | −0.008 (3) | 0.007 (3) |
C57 | 0.025 (3) | 0.019 (3) | 0.029 (3) | −0.003 (2) | 0.000 (3) | 0.011 (2) |
C58 | 0.030 (3) | 0.017 (3) | 0.034 (4) | −0.001 (3) | −0.001 (3) | 0.013 (3) |
C59 | 0.038 (4) | 0.018 (3) | 0.033 (4) | −0.005 (3) | −0.006 (3) | 0.007 (3) |
C60 | 0.076 (7) | 0.045 (5) | 0.038 (5) | −0.003 (5) | −0.008 (5) | 0.004 (4) |
C61 | 0.027 (3) | 0.022 (3) | 0.041 (4) | 0.004 (3) | −0.005 (3) | 0.014 (3) |
C62 | 0.031 (4) | 0.022 (3) | 0.072 (6) | −0.006 (3) | 0.020 (4) | 0.000 (4) |
P1 | 0.0182 (7) | 0.0132 (6) | 0.0186 (7) | 0.0002 (5) | 0.0004 (5) | 0.0053 (5) |
P2 | 0.0183 (7) | 0.0147 (6) | 0.0181 (7) | 0.0006 (5) | 0.0022 (5) | 0.0065 (5) |
Cl1 | 0.0194 (7) | 0.0231 (7) | 0.0319 (8) | 0.0034 (6) | 0.0028 (6) | 0.0115 (6) |
Cl2 | 0.0332 (8) | 0.0170 (6) | 0.0224 (7) | −0.0044 (6) | 0.0021 (6) | 0.0003 (5) |
Cl3 | 0.0167 (7) | 0.0247 (7) | 0.0354 (8) | −0.0018 (6) | −0.0008 (6) | 0.0123 (6) |
Cl4 | 0.0266 (7) | 0.0166 (6) | 0.0203 (6) | 0.0057 (5) | 0.0009 (5) | 0.0028 (5) |
Ru1 | 0.0176 (2) | 0.0132 (2) | 0.0172 (2) | 0.00062 (16) | 0.00045 (17) | 0.00434 (15) |
Ru2 | 0.0164 (2) | 0.0141 (2) | 0.0165 (2) | 0.00081 (17) | 0.00111 (17) | 0.00590 (15) |
O1 | 0.058 (4) | 0.025 (2) | 0.031 (3) | −0.001 (2) | 0.005 (3) | 0.001 (2) |
O2 | 0.029 (3) | 0.020 (2) | 0.045 (3) | 0.005 (2) | −0.012 (2) | 0.009 (2) |
O3 | 0.023 (2) | 0.020 (2) | 0.039 (3) | −0.0046 (18) | −0.001 (2) | 0.011 (2) |
O4 | 0.067 (4) | 0.036 (3) | 0.025 (3) | −0.007 (3) | 0.003 (3) | −0.004 (2) |
O5 | 0.023 (2) | 0.022 (2) | 0.035 (3) | 0.0075 (18) | −0.0001 (19) | 0.0100 (19) |
O6 | 0.029 (3) | 0.019 (2) | 0.049 (3) | −0.0011 (19) | 0.014 (2) | 0.012 (2) |
Geometric parameters (Å, º)
C1—C2 | 1.416 (8) | C32—Ru2 | 2.221 (6) |
C1—C6 | 1.430 (9) | C33—C34 | 1.434 (8) |
C1—C26 | 1.514 (8) | C33—Ru2 | 2.222 (6) |
C1—Ru1 | 2.226 (6) | C33—H33 | 0.95 |
C2—C3 | 1.406 (8) | C34—C35 | 1.402 (9) |
C2—Ru1 | 2.217 (6) | C34—Ru2 | 2.168 (6) |
C2—H2 | 0.95 | C34—H34 | 0.95 |
C3—C4 | 1.408 (10) | C35—C36 | 1.432 (9) |
C3—Ru1 | 2.182 (7) | C35—C56 | 1.494 (9) |
C3—H3 | 0.95 | C35—Ru2 | 2.215 (6) |
C4—C5 | 1.434 (9) | C36—C37 | 1.388 (9) |
C4—C25 | 1.491 (9) | C36—Ru2 | 2.227 (6) |
C4—Ru1 | 2.217 (6) | C36—H36 | 0.95 |
C5—C6 | 1.395 (9) | C37—Ru2 | 2.231 (6) |
C5—Ru1 | 2.221 (6) | C37—H37 | 0.95 |
C5—H5 | 0.95 | C38—C39 | 1.387 (9) |
C6—Ru1 | 2.239 (6) | C38—C43 | 1.410 (9) |
C6—H6 | 0.95 | C38—P2 | 1.825 (6) |
C7—C8 | 1.389 (9) | C39—C40 | 1.387 (10) |
C7—C12 | 1.411 (9) | C39—H39 | 0.95 |
C7—P1 | 1.827 (6) | C40—C41 | 1.396 (11) |
C8—C9 | 1.391 (10) | C40—H40 | 0.95 |
C8—H8 | 0.95 | C41—O4 | 1.368 (9) |
C9—C10 | 1.389 (10) | C41—C42 | 1.386 (11) |
C9—H9 | 0.95 | C42—C43 | 1.384 (9) |
C10—O1 | 1.368 (8) | C42—H42 | 0.95 |
C10—C11 | 1.401 (10) | C43—H43 | 0.95 |
C11—C12 | 1.372 (10) | C44—C49 | 1.396 (9) |
C11—H11 | 0.95 | C44—C45 | 1.408 (8) |
C12—H12 | 0.95 | C44—P2 | 1.824 (6) |
C13—C18 | 1.393 (9) | C45—C46 | 1.399 (8) |
C13—C14 | 1.398 (9) | C45—H45 | 0.95 |
C13—P1 | 1.832 (6) | C46—C47 | 1.383 (9) |
C14—C15 | 1.387 (9) | C46—H46 | 0.95 |
C14—H14 | 0.95 | C47—O5 | 1.367 (7) |
C15—C16 | 1.391 (10) | C47—C48 | 1.392 (9) |
C15—H15 | 0.95 | C48—C49 | 1.389 (9) |
C16—O2 | 1.366 (8) | C48—H48 | 0.95 |
C16—C17 | 1.393 (10) | C49—H49 | 0.95 |
C17—C18 | 1.386 (9) | C50—C55 | 1.392 (9) |
C17—H17 | 0.95 | C50—C51 | 1.400 (9) |
C18—H18 | 0.95 | C50—P2 | 1.827 (6) |
C19—C24 | 1.396 (9) | C51—C52 | 1.384 (9) |
C19—C20 | 1.405 (8) | C51—H51 | 0.95 |
C19—P1 | 1.830 (6) | C52—C53 | 1.384 (10) |
C20—C21 | 1.390 (8) | C52—H52 | 0.95 |
C20—H20 | 0.95 | C53—O6 | 1.369 (8) |
C21—C22 | 1.387 (9) | C53—C54 | 1.393 (9) |
C21—H21 | 0.95 | C54—C55 | 1.387 (9) |
C22—O3 | 1.364 (8) | C54—H54 | 0.95 |
C22—C23 | 1.390 (9) | C55—H55 | 0.95 |
C23—C24 | 1.397 (9) | C56—H56A | 0.98 |
C23—H23 | 0.95 | C56—H56B | 0.98 |
C24—H24 | 0.95 | C56—H56C | 0.98 |
C25—H25A | 0.98 | C57—C59 | 1.530 (10) |
C25—H25B | 0.98 | C57—C58 | 1.539 (8) |
C25—H25C | 0.98 | C57—H57 | 1 |
C26—C28 | 1.521 (9) | C58—H58A | 0.98 |
C26—C27 | 1.526 (8) | C58—H58B | 0.98 |
C26—H26 | 1 | C58—H58C | 0.98 |
C27—H27A | 0.98 | C59—H59A | 0.98 |
C27—H27B | 0.98 | C59—H59B | 0.98 |
C27—H27C | 0.98 | C59—H59C | 0.98 |
C28—H28A | 0.98 | C60—O4 | 1.400 (12) |
C28—H28B | 0.98 | C60—H60A | 0.98 |
C28—H28C | 0.98 | C60—H60B | 0.98 |
C29—O1 | 1.414 (11) | C60—H60C | 0.98 |
C29—H29A | 0.98 | C61—O5 | 1.429 (8) |
C29—H29B | 0.98 | C61—H61A | 0.98 |
C29—H29C | 0.98 | C61—H61B | 0.98 |
C30—O2 | 1.417 (10) | C61—H61C | 0.98 |
C30—H30A | 0.98 | C62—O6 | 1.431 (10) |
C30—H30B | 0.98 | C62—H62A | 0.98 |
C30—H30C | 0.98 | C62—H62B | 0.98 |
C31—O3 | 1.431 (8) | C62—H62C | 0.98 |
C31—H31A | 0.98 | P1—Ru1 | 2.3629 (15) |
C31—H31B | 0.98 | P2—Ru2 | 2.3665 (15) |
C31—H31C | 0.98 | Cl1—Ru1 | 2.4167 (16) |
C32—C33 | 1.403 (8) | Cl2—Ru1 | 2.4068 (16) |
C32—C37 | 1.423 (9) | Cl3—Ru2 | 2.4244 (16) |
C32—C57 | 1.514 (9) | Cl4—Ru2 | 2.4016 (15) |
C2—C1—C6 | 118.3 (5) | O4—C41—C42 | 115.8 (7) |
C2—C1—C26 | 122.8 (6) | O4—C41—C40 | 124.8 (7) |
C6—C1—C26 | 118.8 (5) | C42—C41—C40 | 119.4 (7) |
C2—C1—Ru1 | 71.1 (3) | C43—C42—C41 | 120.9 (7) |
C6—C1—Ru1 | 71.8 (3) | C43—C42—H42 | 119.5 |
C26—C1—Ru1 | 131.3 (4) | C41—C42—H42 | 119.5 |
C3—C2—C1 | 120.1 (6) | C42—C43—C38 | 120.4 (6) |
C3—C2—Ru1 | 70.0 (4) | C42—C43—H43 | 119.8 |
C1—C2—Ru1 | 71.7 (3) | C38—C43—H43 | 119.8 |
C3—C2—H2 | 119.9 | C49—C44—C45 | 118.1 (6) |
C1—C2—H2 | 119.9 | C49—C44—P2 | 123.9 (4) |
Ru1—C2—H2 | 131 | C45—C44—P2 | 118.0 (5) |
C2—C3—C4 | 122.2 (6) | C46—C45—C44 | 121.6 (6) |
C2—C3—Ru1 | 72.7 (4) | C46—C45—H45 | 119.2 |
C4—C3—Ru1 | 72.7 (4) | C44—C45—H45 | 119.2 |
C2—C3—H3 | 118.9 | C47—C46—C45 | 119.3 (6) |
C4—C3—H3 | 118.9 | C47—C46—H46 | 120.4 |
Ru1—C3—H3 | 128 | C45—C46—H46 | 120.4 |
C3—C4—C5 | 117.4 (6) | O5—C47—C46 | 123.9 (6) |
C3—C4—C25 | 122.5 (6) | O5—C47—C48 | 116.3 (6) |
C5—C4—C25 | 120.1 (6) | C46—C47—C48 | 119.8 (6) |
C3—C4—Ru1 | 70.0 (4) | C49—C48—C47 | 121.1 (6) |
C5—C4—Ru1 | 71.3 (3) | C49—C48—H48 | 119.4 |
C25—C4—Ru1 | 130.4 (5) | C47—C48—H48 | 119.4 |
C6—C5—C4 | 121.0 (6) | C48—C49—C44 | 120.2 (6) |
C6—C5—Ru1 | 72.5 (3) | C48—C49—H49 | 119.9 |
C4—C5—Ru1 | 71.0 (3) | C44—C49—H49 | 119.9 |
C6—C5—H5 | 119.5 | C55—C50—C51 | 118.3 (6) |
C4—C5—H5 | 119.5 | C55—C50—P2 | 116.8 (5) |
Ru1—C5—H5 | 129.5 | C51—C50—P2 | 124.5 (5) |
C5—C6—C1 | 120.9 (6) | C52—C51—C50 | 120.6 (6) |
C5—C6—Ru1 | 71.1 (3) | C52—C51—H51 | 119.7 |
C1—C6—Ru1 | 70.8 (3) | C50—C51—H51 | 119.7 |
C5—C6—H6 | 119.5 | C53—C52—C51 | 120.4 (6) |
C1—C6—H6 | 119.5 | C53—C52—H52 | 119.8 |
Ru1—C6—H6 | 131.4 | C51—C52—H52 | 119.8 |
C8—C7—C12 | 117.6 (6) | O6—C53—C52 | 116.4 (6) |
C8—C7—P1 | 121.5 (5) | O6—C53—C54 | 123.7 (7) |
C12—C7—P1 | 120.9 (5) | C52—C53—C54 | 119.9 (6) |
C7—C8—C9 | 121.4 (6) | C55—C54—C53 | 119.4 (6) |
C7—C8—H8 | 119.3 | C55—C54—H54 | 120.3 |
C9—C8—H8 | 119.3 | C53—C54—H54 | 120.3 |
C10—C9—C8 | 119.9 (7) | C54—C55—C50 | 121.5 (6) |
C10—C9—H9 | 120 | C54—C55—H55 | 119.3 |
C8—C9—H9 | 120 | C50—C55—H55 | 119.3 |
O1—C10—C9 | 125.8 (7) | C35—C56—H56A | 109.5 |
O1—C10—C11 | 114.5 (6) | C35—C56—H56B | 109.5 |
C9—C10—C11 | 119.7 (6) | H56A—C56—H56B | 109.5 |
C12—C11—C10 | 119.6 (6) | C35—C56—H56C | 109.5 |
C12—C11—H11 | 120.2 | H56A—C56—H56C | 109.5 |
C10—C11—H11 | 120.2 | H56B—C56—H56C | 109.5 |
C11—C12—C7 | 121.7 (6) | C32—C57—C59 | 114.0 (5) |
C11—C12—H12 | 119.1 | C32—C57—C58 | 107.4 (5) |
C7—C12—H12 | 119.1 | C59—C57—C58 | 111.7 (6) |
C18—C13—C14 | 118.7 (6) | C32—C57—H57 | 107.8 |
C18—C13—P1 | 116.4 (5) | C59—C57—H57 | 107.8 |
C14—C13—P1 | 124.5 (5) | C58—C57—H57 | 107.8 |
C15—C14—C13 | 120.5 (6) | C57—C58—H58A | 109.5 |
C15—C14—H14 | 119.7 | C57—C58—H58B | 109.5 |
C13—C14—H14 | 119.7 | H58A—C58—H58B | 109.5 |
C14—C15—C16 | 120.1 (6) | C57—C58—H58C | 109.5 |
C14—C15—H15 | 119.9 | H58A—C58—H58C | 109.5 |
C16—C15—H15 | 119.9 | H58B—C58—H58C | 109.5 |
O2—C16—C15 | 115.6 (6) | C57—C59—H59A | 109.5 |
O2—C16—C17 | 124.5 (6) | C57—C59—H59B | 109.5 |
C15—C16—C17 | 119.9 (6) | H59A—C59—H59B | 109.5 |
C18—C17—C16 | 119.5 (6) | C57—C59—H59C | 109.5 |
C18—C17—H17 | 120.2 | H59A—C59—H59C | 109.5 |
C16—C17—H17 | 120.2 | H59B—C59—H59C | 109.5 |
C17—C18—C13 | 121.2 (6) | O4—C60—H60A | 109.5 |
C17—C18—H18 | 119.4 | O4—C60—H60B | 109.5 |
C13—C18—H18 | 119.4 | H60A—C60—H60B | 109.5 |
C24—C19—C20 | 117.8 (6) | O4—C60—H60C | 109.5 |
C24—C19—P1 | 124.0 (5) | H60A—C60—H60C | 109.5 |
C20—C19—P1 | 118.2 (5) | H60B—C60—H60C | 109.5 |
C21—C20—C19 | 121.9 (6) | O5—C61—H61A | 109.5 |
C21—C20—H20 | 119.1 | O5—C61—H61B | 109.5 |
C19—C20—H20 | 119.1 | H61A—C61—H61B | 109.5 |
C22—C21—C20 | 119.3 (6) | O5—C61—H61C | 109.5 |
C22—C21—H21 | 120.3 | H61A—C61—H61C | 109.5 |
C20—C21—H21 | 120.3 | H61B—C61—H61C | 109.5 |
O3—C22—C21 | 124.5 (6) | O6—C62—H62A | 109.5 |
O3—C22—C23 | 115.7 (6) | O6—C62—H62B | 109.5 |
C21—C22—C23 | 119.8 (6) | H62A—C62—H62B | 109.5 |
C22—C23—C24 | 120.6 (6) | O6—C62—H62C | 109.5 |
C22—C23—H23 | 119.7 | H62A—C62—H62C | 109.5 |
C24—C23—H23 | 119.7 | H62B—C62—H62C | 109.5 |
C19—C24—C23 | 120.5 (6) | C7—P1—C19 | 102.9 (3) |
C19—C24—H24 | 119.8 | C7—P1—C13 | 104.5 (3) |
C23—C24—H24 | 119.8 | C19—P1—C13 | 99.0 (3) |
C4—C25—H25A | 109.5 | C7—P1—Ru1 | 114.85 (18) |
C4—C25—H25B | 109.5 | C19—P1—Ru1 | 121.1 (2) |
H25A—C25—H25B | 109.5 | C13—P1—Ru1 | 112.2 (2) |
C4—C25—H25C | 109.5 | C38—P2—C44 | 102.3 (3) |
H25A—C25—H25C | 109.5 | C38—P2—C50 | 105.7 (3) |
H25B—C25—H25C | 109.5 | C44—P2—C50 | 99.2 (3) |
C1—C26—C28 | 113.8 (5) | C38—P2—Ru2 | 114.78 (19) |
C1—C26—C27 | 106.8 (5) | C44—P2—Ru2 | 121.3 (2) |
C28—C26—C27 | 112.0 (5) | C50—P2—Ru2 | 111.5 (2) |
C1—C26—H26 | 108.1 | C3—Ru1—C2 | 37.3 (2) |
C28—C26—H26 | 108.1 | C3—Ru1—C4 | 37.3 (3) |
C27—C26—H26 | 108.1 | C2—Ru1—C4 | 67.5 (2) |
C26—C27—H27A | 109.5 | C3—Ru1—C5 | 66.9 (2) |
C26—C27—H27B | 109.5 | C2—Ru1—C5 | 78.9 (2) |
H27A—C27—H27B | 109.5 | C4—Ru1—C5 | 37.7 (2) |
C26—C27—H27C | 109.5 | C3—Ru1—C1 | 67.4 (2) |
H27A—C27—H27C | 109.5 | C2—Ru1—C1 | 37.2 (2) |
H27B—C27—H27C | 109.5 | C4—Ru1—C1 | 80.4 (2) |
C26—C28—H28A | 109.5 | C5—Ru1—C1 | 67.1 (2) |
C26—C28—H28B | 109.5 | C3—Ru1—C6 | 78.6 (2) |
H28A—C28—H28B | 109.5 | C2—Ru1—C6 | 66.5 (2) |
C26—C28—H28C | 109.5 | C4—Ru1—C6 | 67.1 (2) |
H28A—C28—H28C | 109.5 | C5—Ru1—C6 | 36.5 (2) |
H28B—C28—H28C | 109.5 | C1—Ru1—C6 | 37.4 (2) |
O1—C29—H29A | 109.5 | C3—Ru1—P1 | 92.34 (17) |
O1—C29—H29B | 109.5 | C2—Ru1—P1 | 97.58 (16) |
H29A—C29—H29B | 109.5 | C4—Ru1—P1 | 113.67 (18) |
O1—C29—H29C | 109.5 | C5—Ru1—P1 | 150.43 (18) |
H29A—C29—H29C | 109.5 | C1—Ru1—P1 | 125.74 (17) |
H29B—C29—H29C | 109.5 | C6—Ru1—P1 | 162.96 (17) |
O2—C30—H30A | 109.5 | C3—Ru1—Cl2 | 122.15 (17) |
O2—C30—H30B | 109.5 | C2—Ru1—Cl2 | 158.84 (17) |
H30A—C30—H30B | 109.5 | C4—Ru1—Cl2 | 91.80 (17) |
O2—C30—H30C | 109.5 | C5—Ru1—Cl2 | 87.36 (17) |
H30A—C30—H30C | 109.5 | C1—Ru1—Cl2 | 147.33 (17) |
H30B—C30—H30C | 109.5 | C6—Ru1—Cl2 | 110.54 (17) |
O3—C31—H31A | 109.5 | P1—Ru1—Cl2 | 86.50 (5) |
O3—C31—H31B | 109.5 | C3—Ru1—Cl1 | 149.35 (17) |
H31A—C31—H31B | 109.5 | C2—Ru1—Cl1 | 112.33 (16) |
O3—C31—H31C | 109.5 | C4—Ru1—Cl1 | 158.28 (18) |
H31A—C31—H31C | 109.5 | C5—Ru1—Cl1 | 120.70 (18) |
H31B—C31—H31C | 109.5 | C1—Ru1—Cl1 | 87.69 (17) |
C33—C32—C37 | 118.3 (6) | C6—Ru1—Cl1 | 92.52 (16) |
C33—C32—C57 | 121.8 (6) | P1—Ru1—Cl1 | 88.03 (5) |
C37—C32—C57 | 119.7 (5) | Cl2—Ru1—Cl1 | 88.47 (6) |
C33—C32—Ru2 | 71.6 (3) | C34—Ru2—C35 | 37.3 (2) |
C37—C32—Ru2 | 71.8 (3) | C34—Ru2—C33 | 38.1 (2) |
C57—C32—Ru2 | 131.7 (4) | C35—Ru2—C33 | 68.0 (2) |
C32—C33—C34 | 119.6 (6) | C34—Ru2—C32 | 67.9 (2) |
C32—C33—Ru2 | 71.5 (3) | C35—Ru2—C32 | 80.8 (2) |
C34—C33—Ru2 | 68.9 (3) | C33—Ru2—C32 | 36.8 (2) |
C32—C33—H33 | 120.2 | C34—Ru2—C36 | 66.7 (2) |
C34—C33—H33 | 120.2 | C35—Ru2—C36 | 37.6 (2) |
Ru2—C33—H33 | 132.3 | C33—Ru2—C36 | 78.6 (2) |
C35—C34—C33 | 122.1 (6) | C32—Ru2—C36 | 67.0 (2) |
C35—C34—Ru2 | 73.2 (4) | C34—Ru2—C37 | 78.7 (2) |
C33—C34—Ru2 | 73.0 (3) | C35—Ru2—C37 | 67.1 (2) |
C35—C34—H34 | 119 | C33—Ru2—C37 | 66.0 (2) |
C33—C34—H34 | 119 | C32—Ru2—C37 | 37.3 (2) |
Ru2—C34—H34 | 127 | C36—Ru2—C37 | 36.3 (2) |
C34—C35—C36 | 117.1 (6) | C34—Ru2—P2 | 92.57 (17) |
C34—C35—C56 | 122.6 (6) | C35—Ru2—P2 | 113.98 (17) |
C36—C35—C56 | 120.3 (6) | C33—Ru2—P2 | 98.15 (16) |
C34—C35—Ru2 | 69.5 (4) | C32—Ru2—P2 | 125.91 (17) |
C36—C35—Ru2 | 71.6 (4) | C36—Ru2—P2 | 150.73 (18) |
C56—C35—Ru2 | 131.2 (4) | C37—Ru2—P2 | 163.06 (18) |
C37—C36—C35 | 121.2 (6) | C34—Ru2—Cl4 | 121.57 (17) |
C37—C36—Ru2 | 72.0 (4) | C35—Ru2—Cl4 | 91.48 (17) |
C35—C36—Ru2 | 70.8 (4) | C33—Ru2—Cl4 | 159.07 (17) |
C37—C36—H36 | 119.4 | C32—Ru2—Cl4 | 147.58 (17) |
C35—C36—H36 | 119.4 | C36—Ru2—Cl4 | 87.74 (17) |
Ru2—C36—H36 | 130.5 | C37—Ru2—Cl4 | 110.89 (17) |
C36—C37—C32 | 121.5 (6) | P2—Ru2—Cl4 | 86.05 (5) |
C36—C37—Ru2 | 71.7 (4) | C34—Ru2—Cl3 | 149.64 (17) |
C32—C37—Ru2 | 71.0 (3) | C35—Ru2—Cl3 | 157.78 (17) |
C36—C37—H37 | 119.2 | C33—Ru2—Cl3 | 111.78 (17) |
C32—C37—H37 | 119.2 | C32—Ru2—Cl3 | 87.18 (16) |
Ru2—C37—H37 | 131 | C36—Ru2—Cl3 | 120.25 (18) |
C39—C38—C43 | 117.7 (6) | C37—Ru2—Cl3 | 92.11 (17) |
C39—C38—P2 | 122.9 (5) | P2—Ru2—Cl3 | 88.21 (6) |
C43—C38—P2 | 119.3 (5) | Cl4—Ru2—Cl3 | 88.77 (6) |
C40—C39—C38 | 122.2 (6) | C10—O1—C29 | 117.0 (6) |
C40—C39—H39 | 118.9 | C16—O2—C30 | 117.1 (6) |
C38—C39—H39 | 118.9 | C22—O3—C31 | 116.5 (5) |
C39—C40—C41 | 119.4 (7) | C41—O4—C60 | 119.1 (7) |
C39—C40—H40 | 120.3 | C47—O5—C61 | 116.8 (5) |
C41—C40—H40 | 120.3 | C53—O6—C62 | 117.7 (6) |
C6—C1—C2—C3 | 3.4 (9) | C6—C5—Ru1—C3 | 102.4 (4) |
C26—C1—C2—C3 | 179.9 (6) | C4—C5—Ru1—C3 | −30.4 (4) |
Ru1—C1—C2—C3 | −52.6 (5) | C6—C5—Ru1—C2 | 65.3 (4) |
C6—C1—C2—Ru1 | 56.0 (5) | C4—C5—Ru1—C2 | −67.5 (4) |
C26—C1—C2—Ru1 | −127.5 (6) | C6—C5—Ru1—C4 | 132.8 (6) |
C1—C2—C3—C4 | −2.3 (9) | C6—C5—Ru1—C1 | 28.3 (4) |
Ru1—C2—C3—C4 | −55.6 (5) | C4—C5—Ru1—C1 | −104.5 (4) |
C1—C2—C3—Ru1 | 53.4 (5) | C4—C5—Ru1—C6 | −132.8 (6) |
C2—C3—C4—C5 | 0.6 (9) | C6—C5—Ru1—P1 | 151.0 (3) |
Ru1—C3—C4—C5 | −55.0 (5) | C4—C5—Ru1—P1 | 18.2 (6) |
C2—C3—C4—C25 | −178.5 (6) | C6—C5—Ru1—Cl2 | −130.8 (4) |
Ru1—C3—C4—C25 | 125.9 (6) | C4—C5—Ru1—Cl2 | 96.4 (3) |
C2—C3—C4—Ru1 | 55.7 (5) | C6—C5—Ru1—Cl1 | −44.1 (4) |
C3—C4—C5—C6 | −0.3 (9) | C4—C5—Ru1—Cl1 | −177.0 (3) |
C25—C4—C5—C6 | 178.8 (6) | C2—C1—Ru1—C3 | 28.7 (4) |
Ru1—C4—C5—C6 | −54.7 (5) | C6—C1—Ru1—C3 | −101.1 (4) |
C3—C4—C5—Ru1 | 54.4 (5) | C26—C1—Ru1—C3 | 146.1 (7) |
C25—C4—C5—Ru1 | −126.5 (6) | C6—C1—Ru1—C2 | −129.8 (5) |
C4—C5—C6—C1 | 1.6 (9) | C26—C1—Ru1—C2 | 117.5 (7) |
Ru1—C5—C6—C1 | −52.4 (5) | C2—C1—Ru1—C4 | 65.2 (4) |
C4—C5—C6—Ru1 | 54.0 (5) | C6—C1—Ru1—C4 | −64.6 (4) |
C2—C1—C6—C5 | −3.1 (9) | C26—C1—Ru1—C4 | −177.3 (6) |
C26—C1—C6—C5 | −179.7 (6) | C2—C1—Ru1—C5 | 102.1 (4) |
Ru1—C1—C6—C5 | 52.5 (5) | C6—C1—Ru1—C5 | −27.7 (4) |
C2—C1—C6—Ru1 | −55.7 (5) | C26—C1—Ru1—C5 | −140.5 (7) |
C26—C1—C6—Ru1 | 127.7 (5) | C2—C1—Ru1—C6 | 129.8 (5) |
C12—C7—C8—C9 | 0.0 (9) | C26—C1—Ru1—C6 | −112.8 (7) |
P1—C7—C8—C9 | 178.9 (5) | C2—C1—Ru1—P1 | −47.1 (4) |
C7—C8—C9—C10 | −1.4 (10) | C6—C1—Ru1—P1 | −176.9 (3) |
C8—C9—C10—O1 | −179.6 (6) | C26—C1—Ru1—P1 | 70.3 (6) |
C8—C9—C10—C11 | 1.1 (10) | C2—C1—Ru1—Cl2 | 143.4 (3) |
O1—C10—C11—C12 | −178.7 (6) | C6—C1—Ru1—Cl2 | 13.6 (5) |
C9—C10—C11—C12 | 0.6 (10) | C26—C1—Ru1—Cl2 | −99.1 (6) |
C10—C11—C12—C7 | −2.1 (9) | C2—C1—Ru1—Cl1 | −133.0 (4) |
C8—C7—C12—C11 | 1.8 (9) | C6—C1—Ru1—Cl1 | 97.2 (3) |
P1—C7—C12—C11 | −177.2 (5) | C26—C1—Ru1—Cl1 | −15.6 (6) |
C18—C13—C14—C15 | −0.1 (9) | C5—C6—Ru1—C3 | −66.4 (4) |
P1—C13—C14—C15 | −171.6 (5) | C1—C6—Ru1—C3 | 67.5 (4) |
C13—C14—C15—C16 | −0.2 (10) | C5—C6—Ru1—C2 | −103.5 (4) |
C14—C15—C16—O2 | 179.8 (6) | C1—C6—Ru1—C2 | 30.4 (4) |
C14—C15—C16—C17 | 0.6 (10) | C5—C6—Ru1—C4 | −29.1 (4) |
O2—C16—C17—C18 | −179.7 (6) | C1—C6—Ru1—C4 | 104.8 (4) |
C15—C16—C17—C18 | −0.6 (10) | C1—C6—Ru1—C5 | 134.0 (6) |
C16—C17—C18—C13 | 0.3 (10) | C5—C6—Ru1—C1 | −134.0 (6) |
C14—C13—C18—C17 | 0.1 (9) | C5—C6—Ru1—P1 | −125.4 (5) |
P1—C13—C18—C17 | 172.2 (5) | C1—C6—Ru1—P1 | 8.6 (8) |
C24—C19—C20—C21 | 0.0 (10) | C5—C6—Ru1—Cl2 | 53.9 (4) |
P1—C19—C20—C21 | −179.1 (5) | C1—C6—Ru1—Cl2 | −172.2 (3) |
C19—C20—C21—C22 | 0.2 (10) | C5—C6—Ru1—Cl1 | 143.2 (4) |
C20—C21—C22—O3 | −179.4 (6) | C1—C6—Ru1—Cl1 | −82.9 (3) |
C20—C21—C22—C23 | −0.2 (10) | C7—P1—Ru1—C3 | −80.9 (3) |
O3—C22—C23—C24 | 179.2 (6) | C19—P1—Ru1—C3 | 154.6 (3) |
C21—C22—C23—C24 | −0.1 (10) | C13—P1—Ru1—C3 | 38.2 (3) |
C20—C19—C24—C23 | −0.3 (10) | C7—P1—Ru1—C2 | −43.8 (3) |
P1—C19—C24—C23 | 178.9 (5) | C19—P1—Ru1—C2 | −168.4 (3) |
C22—C23—C24—C19 | 0.3 (10) | C13—P1—Ru1—C2 | 75.3 (3) |
C2—C1—C26—C28 | 21.7 (8) | C7—P1—Ru1—C4 | −112.6 (3) |
C6—C1—C26—C28 | −161.8 (6) | C19—P1—Ru1—C4 | 122.9 (3) |
Ru1—C1—C26—C28 | −71.3 (8) | C13—P1—Ru1—C4 | 6.6 (3) |
C2—C1—C26—C27 | −102.3 (7) | C7—P1—Ru1—C5 | −124.6 (4) |
C6—C1—C26—C27 | 74.2 (7) | C19—P1—Ru1—C5 | 110.9 (4) |
Ru1—C1—C26—C27 | 164.7 (5) | C13—P1—Ru1—C5 | −5.4 (4) |
C37—C32—C33—C34 | 5.1 (8) | C7—P1—Ru1—C1 | −17.3 (3) |
C57—C32—C33—C34 | −179.5 (5) | C19—P1—Ru1—C1 | −141.8 (3) |
Ru2—C32—C33—C34 | −51.3 (5) | C13—P1—Ru1—C1 | 101.8 (3) |
C37—C32—C33—Ru2 | 56.4 (5) | C7—P1—Ru1—C6 | −23.7 (6) |
C57—C32—C33—Ru2 | −128.2 (5) | C19—P1—Ru1—C6 | −148.2 (6) |
C32—C33—C34—C35 | −4.2 (9) | C13—P1—Ru1—C6 | 95.4 (6) |
Ru2—C33—C34—C35 | −56.7 (5) | C7—P1—Ru1—Cl2 | 157.0 (2) |
C32—C33—C34—Ru2 | 52.4 (5) | C19—P1—Ru1—Cl2 | 32.5 (2) |
C33—C34—C35—C36 | 1.2 (9) | C13—P1—Ru1—Cl2 | −83.8 (2) |
Ru2—C34—C35—C36 | −55.3 (5) | C7—P1—Ru1—Cl1 | 68.4 (2) |
C33—C34—C35—C56 | −176.9 (6) | C19—P1—Ru1—Cl1 | −56.1 (2) |
Ru2—C34—C35—C56 | 126.6 (6) | C13—P1—Ru1—Cl1 | −172.4 (2) |
C33—C34—C35—Ru2 | 56.6 (5) | C33—C34—Ru2—C35 | −132.3 (5) |
C34—C35—C36—C37 | 0.7 (9) | C35—C34—Ru2—C33 | 132.3 (5) |
C56—C35—C36—C37 | 178.8 (6) | C35—C34—Ru2—C32 | 104.3 (4) |
Ru2—C35—C36—C37 | −53.6 (5) | C33—C34—Ru2—C32 | −28.0 (3) |
C34—C35—C36—Ru2 | 54.3 (5) | C35—C34—Ru2—C36 | 30.9 (3) |
C56—C35—C36—Ru2 | −127.6 (6) | C33—C34—Ru2—C36 | −101.4 (4) |
C35—C36—C37—C32 | 0.4 (9) | C35—C34—Ru2—C37 | 66.9 (4) |
Ru2—C36—C37—C32 | −52.7 (5) | C33—C34—Ru2—C37 | −65.4 (4) |
C35—C36—C37—Ru2 | 53.0 (5) | C35—C34—Ru2—P2 | −127.8 (3) |
C33—C32—C37—C36 | −3.3 (9) | C33—C34—Ru2—P2 | 99.9 (3) |
C57—C32—C37—C36 | −178.8 (6) | C35—C34—Ru2—Cl4 | −40.8 (4) |
Ru2—C32—C37—C36 | 53.0 (5) | C33—C34—Ru2—Cl4 | −173.1 (3) |
C33—C32—C37—Ru2 | −56.3 (5) | C35—C34—Ru2—Cl3 | 141.4 (3) |
C57—C32—C37—Ru2 | 128.2 (5) | C33—C34—Ru2—Cl3 | 9.1 (6) |
C43—C38—C39—C40 | 0.8 (9) | C36—C35—Ru2—C34 | 129.5 (5) |
P2—C38—C39—C40 | 177.7 (5) | C56—C35—Ru2—C34 | −116.0 (8) |
C38—C39—C40—C41 | −2.0 (10) | C34—C35—Ru2—C33 | −29.5 (3) |
C39—C40—C41—O4 | −179.4 (6) | C36—C35—Ru2—C33 | 100.0 (4) |
C39—C40—C41—C42 | 1.7 (10) | C56—C35—Ru2—C33 | −145.5 (7) |
O4—C41—C42—C43 | −179.1 (6) | C34—C35—Ru2—C32 | −65.5 (4) |
C40—C41—C42—C43 | −0.1 (9) | C36—C35—Ru2—C32 | 64.0 (4) |
C41—C42—C43—C38 | −1.1 (9) | C56—C35—Ru2—C32 | 178.5 (7) |
C39—C38—C43—C42 | 0.8 (9) | C34—C35—Ru2—C36 | −129.5 (5) |
P2—C38—C43—C42 | −176.2 (5) | C56—C35—Ru2—C36 | 114.5 (8) |
C49—C44—C45—C46 | −0.4 (10) | C34—C35—Ru2—C37 | −101.8 (4) |
P2—C44—C45—C46 | −180.0 (5) | C36—C35—Ru2—C37 | 27.7 (4) |
C44—C45—C46—C47 | 0.1 (11) | C56—C35—Ru2—C37 | 142.3 (7) |
C45—C46—C47—O5 | −180.0 (6) | C34—C35—Ru2—P2 | 59.8 (3) |
C45—C46—C47—C48 | 0.4 (10) | C36—C35—Ru2—P2 | −170.7 (3) |
O5—C47—C48—C49 | 179.7 (6) | C56—C35—Ru2—P2 | −56.2 (7) |
C46—C47—C48—C49 | −0.7 (10) | C34—C35—Ru2—Cl4 | 146.1 (3) |
C47—C48—C49—C44 | 0.4 (10) | C36—C35—Ru2—Cl4 | −84.4 (3) |
C45—C44—C49—C48 | 0.2 (10) | C56—C35—Ru2—Cl4 | 30.2 (6) |
P2—C44—C49—C48 | 179.7 (5) | C34—C35—Ru2—Cl3 | −123.5 (4) |
C55—C50—C51—C52 | −0.2 (9) | C36—C35—Ru2—Cl3 | 6.0 (7) |
P2—C50—C51—C52 | −172.1 (5) | C56—C35—Ru2—Cl3 | 120.5 (6) |
C50—C51—C52—C53 | −0.4 (10) | C32—C33—Ru2—C34 | −133.4 (6) |
C51—C52—C53—O6 | 179.9 (6) | C32—C33—Ru2—C35 | −104.5 (4) |
C51—C52—C53—C54 | 0.7 (10) | C34—C33—Ru2—C35 | 28.9 (4) |
O6—C53—C54—C55 | −179.6 (6) | C34—C33—Ru2—C32 | 133.4 (6) |
C52—C53—C54—C55 | −0.5 (10) | C32—C33—Ru2—C36 | −66.7 (4) |
C53—C54—C55—C50 | −0.1 (10) | C34—C33—Ru2—C36 | 66.7 (4) |
C51—C50—C55—C54 | 0.5 (9) | C32—C33—Ru2—C37 | −30.8 (4) |
P2—C50—C55—C54 | 173.0 (5) | C34—C33—Ru2—C37 | 102.6 (4) |
C33—C32—C57—C59 | 22.4 (8) | C32—C33—Ru2—P2 | 142.9 (3) |
C37—C32—C57—C59 | −162.3 (6) | C34—C33—Ru2—P2 | −83.7 (3) |
Ru2—C32—C57—C59 | −70.9 (8) | C32—C33—Ru2—Cl4 | −116.8 (5) |
C33—C32—C57—C58 | −101.9 (7) | C34—C33—Ru2—Cl4 | 16.6 (7) |
C37—C32—C57—C58 | 73.4 (7) | C32—C33—Ru2—Cl3 | 51.5 (4) |
Ru2—C32—C57—C58 | 164.8 (5) | C34—C33—Ru2—Cl3 | −175.1 (3) |
C8—C7—P1—C19 | 16.9 (5) | C33—C32—Ru2—C34 | 28.9 (4) |
C12—C7—P1—C19 | −164.2 (5) | C37—C32—Ru2—C34 | −100.6 (4) |
C8—C7—P1—C13 | 119.9 (5) | C57—C32—Ru2—C34 | 145.6 (7) |
C12—C7—P1—C13 | −61.2 (5) | C33—C32—Ru2—C35 | 65.5 (4) |
C8—C7—P1—Ru1 | −116.7 (4) | C37—C32—Ru2—C35 | −64.1 (4) |
C12—C7—P1—Ru1 | 62.1 (5) | C57—C32—Ru2—C35 | −177.9 (6) |
C24—C19—P1—C7 | −103.7 (6) | C37—C32—Ru2—C33 | −129.5 (6) |
C20—C19—P1—C7 | 75.4 (6) | C57—C32—Ru2—C33 | 116.6 (8) |
C24—C19—P1—C13 | 149.0 (6) | C33—C32—Ru2—C36 | 102.0 (4) |
C20—C19—P1—C13 | −31.9 (6) | C37—C32—Ru2—C36 | −27.5 (4) |
C24—C19—P1—Ru1 | 26.2 (7) | C57—C32—Ru2—C36 | −141.3 (7) |
C20—C19—P1—Ru1 | −154.7 (4) | C33—C32—Ru2—C37 | 129.5 (6) |
C18—C13—P1—C7 | −177.0 (5) | C57—C32—Ru2—C37 | −113.9 (7) |
C14—C13—P1—C7 | −5.3 (6) | C33—C32—Ru2—P2 | −47.5 (4) |
C18—C13—P1—C19 | −71.0 (5) | C37—C32—Ru2—P2 | −177.0 (3) |
C14—C13—P1—C19 | 100.7 (6) | C57—C32—Ru2—P2 | 69.1 (6) |
C18—C13—P1—Ru1 | 58.0 (5) | C33—C32—Ru2—Cl4 | 143.5 (3) |
C14—C13—P1—Ru1 | −130.4 (5) | C37—C32—Ru2—Cl4 | 14.0 (5) |
C39—C38—P2—C44 | 18.3 (6) | C57—C32—Ru2—Cl4 | −99.9 (6) |
C43—C38—P2—C44 | −164.8 (5) | C33—C32—Ru2—Cl3 | −133.3 (4) |
C39—C38—P2—C50 | 121.7 (5) | C37—C32—Ru2—Cl3 | 97.2 (3) |
C43—C38—P2—C50 | −61.4 (5) | C57—C32—Ru2—Cl3 | −16.6 (6) |
C39—C38—P2—Ru2 | −115.0 (5) | C37—C36—Ru2—C34 | 103.0 (4) |
C43—C38—P2—Ru2 | 61.8 (5) | C35—C36—Ru2—C34 | −30.6 (3) |
C49—C44—P2—C38 | −105.7 (6) | C37—C36—Ru2—C35 | 133.6 (6) |
C45—C44—P2—C38 | 73.8 (6) | C37—C36—Ru2—C33 | 64.9 (4) |
C49—C44—P2—C50 | 145.9 (6) | C35—C36—Ru2—C33 | −68.7 (4) |
C45—C44—P2—C50 | −34.6 (6) | C37—C36—Ru2—C32 | 28.2 (4) |
C49—C44—P2—Ru2 | 23.7 (7) | C35—C36—Ru2—C32 | −105.4 (4) |
C45—C44—P2—Ru2 | −156.8 (4) | C35—C36—Ru2—C37 | −133.6 (6) |
C55—C50—P2—C38 | −177.2 (5) | C37—C36—Ru2—P2 | 151.2 (3) |
C51—C50—P2—C38 | −5.1 (6) | C35—C36—Ru2—P2 | 17.6 (6) |
C55—C50—P2—C44 | −71.5 (5) | C37—C36—Ru2—Cl4 | −131.0 (4) |
C51—C50—P2—C44 | 100.5 (6) | C35—C36—Ru2—Cl4 | 95.4 (3) |
C55—C50—P2—Ru2 | 57.5 (5) | C37—C36—Ru2—Cl3 | −43.8 (4) |
C51—C50—P2—Ru2 | −130.5 (5) | C35—C36—Ru2—Cl3 | −177.4 (3) |
C4—C3—Ru1—C2 | 133.0 (5) | C36—C37—Ru2—C34 | −65.9 (4) |
C2—C3—Ru1—C4 | −133.0 (5) | C32—C37—Ru2—C34 | 68.3 (4) |
C2—C3—Ru1—C5 | −102.3 (4) | C36—C37—Ru2—C35 | −28.7 (4) |
C4—C3—Ru1—C5 | 30.7 (4) | C32—C37—Ru2—C35 | 105.5 (4) |
C2—C3—Ru1—C1 | −28.6 (3) | C36—C37—Ru2—C33 | −103.8 (4) |
C4—C3—Ru1—C1 | 104.4 (4) | C32—C37—Ru2—C33 | 30.4 (4) |
C2—C3—Ru1—C6 | −66.0 (4) | C36—C37—Ru2—C32 | −134.2 (6) |
C4—C3—Ru1—C6 | 67.0 (4) | C32—C37—Ru2—C36 | 134.2 (6) |
C2—C3—Ru1—P1 | 99.5 (3) | C36—C37—Ru2—P2 | −125.9 (6) |
C4—C3—Ru1—P1 | −127.6 (3) | C32—C37—Ru2—P2 | 8.3 (8) |
C2—C3—Ru1—Cl2 | −173.2 (3) | C36—C37—Ru2—Cl4 | 53.8 (4) |
C4—C3—Ru1—Cl2 | −40.2 (4) | C32—C37—Ru2—Cl4 | −172.0 (3) |
C2—C3—Ru1—Cl1 | 9.4 (6) | C36—C37—Ru2—Cl3 | 143.3 (4) |
C4—C3—Ru1—Cl1 | 142.4 (3) | C32—C37—Ru2—Cl3 | −82.5 (3) |
C1—C2—Ru1—C3 | −133.0 (5) | C38—P2—Ru2—C34 | −80.6 (3) |
C3—C2—Ru1—C4 | 28.7 (4) | C44—P2—Ru2—C34 | 155.7 (3) |
C1—C2—Ru1—C4 | −104.3 (4) | C50—P2—Ru2—C34 | 39.5 (3) |
C3—C2—Ru1—C5 | 66.4 (4) | C38—P2—Ru2—C35 | −112.2 (3) |
C1—C2—Ru1—C5 | −66.7 (4) | C44—P2—Ru2—C35 | 124.1 (3) |
C3—C2—Ru1—C1 | 133.0 (5) | C50—P2—Ru2—C35 | 7.9 (3) |
C3—C2—Ru1—C6 | 102.4 (4) | C38—P2—Ru2—C33 | −42.7 (3) |
C1—C2—Ru1—C6 | −30.6 (4) | C44—P2—Ru2—C33 | −166.4 (3) |
C3—C2—Ru1—P1 | −83.9 (3) | C50—P2—Ru2—C33 | 77.4 (3) |
C1—C2—Ru1—P1 | 143.1 (3) | C38—P2—Ru2—C32 | −16.1 (3) |
C3—C2—Ru1—Cl2 | 16.1 (7) | C44—P2—Ru2—C32 | −139.9 (3) |
C1—C2—Ru1—Cl2 | −116.9 (5) | C50—P2—Ru2—C32 | 104.0 (3) |
C3—C2—Ru1—Cl1 | −174.8 (3) | C38—P2—Ru2—C36 | −123.8 (4) |
C1—C2—Ru1—Cl1 | 52.1 (4) | C44—P2—Ru2—C36 | 112.4 (4) |
C5—C4—Ru1—C3 | 129.8 (5) | C50—P2—Ru2—C36 | −3.7 (4) |
C25—C4—Ru1—C3 | −116.1 (8) | C38—P2—Ru2—C37 | −22.3 (6) |
C3—C4—Ru1—C2 | −28.6 (3) | C44—P2—Ru2—C37 | −146.1 (6) |
C5—C4—Ru1—C2 | 101.2 (4) | C50—P2—Ru2—C37 | 97.8 (6) |
C25—C4—Ru1—C2 | −144.8 (8) | C38—P2—Ru2—Cl4 | 158.0 (2) |
C3—C4—Ru1—C5 | −129.8 (5) | C44—P2—Ru2—Cl4 | 34.2 (2) |
C25—C4—Ru1—C5 | 114.0 (8) | C50—P2—Ru2—Cl4 | −81.9 (2) |
C3—C4—Ru1—C1 | −65.1 (4) | C38—P2—Ru2—Cl3 | 69.1 (2) |
C5—C4—Ru1—C1 | 64.8 (4) | C44—P2—Ru2—Cl3 | −54.7 (2) |
C25—C4—Ru1—C1 | 178.8 (7) | C50—P2—Ru2—Cl3 | −170.8 (2) |
C3—C4—Ru1—C6 | −101.6 (4) | C9—C10—O1—C29 | −4.5 (11) |
C5—C4—Ru1—C6 | 28.2 (4) | C11—C10—O1—C29 | 174.9 (7) |
C25—C4—Ru1—C6 | 142.3 (8) | C15—C16—O2—C30 | 175.7 (6) |
C3—C4—Ru1—P1 | 59.9 (4) | C17—C16—O2—C30 | −5.1 (10) |
C5—C4—Ru1—P1 | −170.3 (3) | C21—C22—O3—C31 | 1.0 (10) |
C25—C4—Ru1—P1 | −56.3 (7) | C23—C22—O3—C31 | −178.3 (6) |
C3—C4—Ru1—Cl2 | 146.8 (3) | C42—C41—O4—C60 | 174.0 (7) |
C5—C4—Ru1—Cl2 | −83.3 (3) | C40—C41—O4—C60 | −4.9 (11) |
C25—C4—Ru1—Cl2 | 30.7 (7) | C46—C47—O5—C61 | 3.3 (10) |
C3—C4—Ru1—Cl1 | −122.8 (5) | C48—C47—O5—C61 | −177.1 (6) |
C5—C4—Ru1—Cl1 | 7.1 (7) | C52—C53—O6—C62 | 174.5 (6) |
C25—C4—Ru1—Cl1 | 121.1 (6) | C54—C53—O6—C62 | −6.3 (10) |
Hydrogen-bond geometry (Å, º)
Cg1 is the centroid of the C1–C6 ring.
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cl2i | 0.95 | 2.62 | 3.566 (7) | 171 |
C36—H36···Cl4ii | 0.95 | 2.6 | 3.506 (7) | 159 |
C43—H43···Cl1iii | 0.95 | 2.78 | 3.619 (7) | 147 |
C62—H62B···O5iii | 0.98 | 2.58 | 3.362 (9) | 136 |
C18—H18···Cl2 | 0.95 | 2.8 | 3.643 (7) | 149 |
C24—H24···Cl1 | 0.95 | 2.62 | 3.427 (6) | 143 |
C49—H49···Cl3 | 0.95 | 2.61 | 3.416 (6) | 143 |
C55—H55···Cl4 | 0.95 | 2.71 | 3.562 (6) | 149 |
C20—H20···Cg1 | 0.95 | 2.95 | 3.614 (7) | 128 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y, −z; (iii) x−1, y, z.
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2414314621012591/tk4072sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2414314621012591/tk4072Isup2.hkl
CCDC reference: 2124507
Additional supporting information: crystallographic information; 3D view; checkCIF report