metal-organic compounds
[μ-Bis(diphenylphosphino)methane-1:2κ2P:P′]nonacarbonyl-1κ3C,2κ3C,3κ3C-[tris(4-methylphenyl)arsine-3κAs]-triangulo-triruthenium(0)
aChemical Sciences Programme, School of Distance Education, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: omarsa@usm.my
In the title triangulo-triruthenium compound, [Ru3(C21H21As)(C25H22P2)(CO)9], the bis(diphenylphosphino)methane ligand bridges an Ru—Ru bond and the monodentate arsine ligand bonds to the third Ru atom. Both the phosphine and arsine ligands are equatorial with respect to the Ru3 triangle. Additionally, each Ru atom carries one equatorial and two axial terminal carbonyl ligands. The three arsine-substituted phenyl rings make dihedral angles of 87.36 (10), 81.96 (10) and 73.37 (11)° with each other. The dihedral angles between the two phenyl rings are 88.08 (12) and 80.15 (10)° for the two diphenylphosphino groups. In the crystal packing, the molecules are linked together as dimers via intermolecular C—H⋯O hydrogen bonds. These dimers are stacked down b axis. Intermolecular C—H⋯π and π–π interactions [centroid–centroid distance = 3.6383 (13) Å] further stabilize the crystal structure.
Related literature
For general background to triangulo-triruthenium derivatives, see: Bruce et al. (1985, 1988a, 1988b); Shawkataly et al. (1998, 2009a). For related structures, see: Shawkataly et al. (2006, 2009a,b,c). For the synthesis of bis(diphenylphosphino)methane, see: Bruce et al. (1983). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536809046704/sj2670sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809046704/sj2670Isup2.hkl
Reactions were conducted under an atmosphere of nitrogen using standard Schlenk techniques and hexane-dried over sodium metal. Tris(4-methylphenyl)arsine (Maybridge) is used as received and bis(diphenylphosphino)methane (Bruce et al., 1983) was prepared by a reported procedure. Ru3(CO)10(µ-Ph2PCH2PPh2) (102.4 mg, 0.1 mmol) and tris(p-tolyl)arsine (34.83 mg, 0.1 mmol) were refluxed for 15 minutes in hexane (25 ml) under a current of nitrogen. The reaction mixture turned intense red. The solvent was removed under vacuum. The reaction mixture was separated by TLC (dichloromethane:hexane, 30:70). Two bands appeared. The major band (red) Rf = 0.56 yielded the title compound which was crystallized from CH2Cl2 - CH3OH, yield = 60 mg, 43.73%, m.p. 197–200 °C. IR(cyclohexane).ν(CO) 2082 s, 2000 s, 1981 s, cm-1. 1H NMR (CDCl3), δ 7.144–7.499 (32H, Ph), δ 4.185–4.336 (m, 2H, –CH2–), δ 2.365 (s, 9H, 3CH3).
All hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was used for the methyl groups.
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound with 30% probability ellipsoids for non-H atoms. | |
Fig. 2. The crystal packing of the title compound, viewed down the b axis, showing the molecular dimers stacked down b axis. Hydrogen atoms that not involved in the hydrogen-bonding (dashed lines) have been omitted for clarity. |
[Ru3(C21H21As)(C25H22P2)(CO)9] | Z = 2 |
Mr = 1287.96 | F(000) = 1280 |
Triclinic, P1 | Dx = 1.646 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.1241 (1) Å | Cell parameters from 9275 reflections |
b = 12.1660 (2) Å | θ = 2.4–36.0° |
c = 20.0895 (3) Å | µ = 1.61 mm−1 |
α = 91.406 (1)° | T = 100 K |
β = 101.116 (1)° | Plate, red |
γ = 102.473 (1)° | 0.29 × 0.22 × 0.06 mm |
V = 2598.63 (6) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 24677 independent reflections |
Radiation source: fine-focus sealed tube | 19683 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 36.2°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −18→18 |
Tmin = 0.653, Tmax = 0.907 | k = −20→19 |
104298 measured reflections | l = −33→32 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0322P)2 + 3.0613P] where P = (Fo2 + 2Fc2)/3 |
24677 reflections | (Δ/σ)max = 0.001 |
634 parameters | Δρmax = 3.41 e Å−3 |
0 restraints | Δρmin = −1.34 e Å−3 |
[Ru3(C21H21As)(C25H22P2)(CO)9] | γ = 102.473 (1)° |
Mr = 1287.96 | V = 2598.63 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.1241 (1) Å | Mo Kα radiation |
b = 12.1660 (2) Å | µ = 1.61 mm−1 |
c = 20.0895 (3) Å | T = 100 K |
α = 91.406 (1)° | 0.29 × 0.22 × 0.06 mm |
β = 101.116 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 24677 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 19683 reflections with I > 2σ(I) |
Tmin = 0.653, Tmax = 0.907 | Rint = 0.035 |
104298 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.02 | Δρmax = 3.41 e Å−3 |
24677 reflections | Δρmin = −1.34 e Å−3 |
634 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. IR spectra was recorded with a Matson 1000 FTIR spectrometer in a NaCl solution cell (0.1 mm). NMR spectra recorded in CDCl3 with a Bruker 400 MHz s pectrometer. |
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 | ||
Ru1 | −0.092501 (13) | 0.023179 (12) | 0.225967 (7) | 0.01420 (3) | |
Ru2 | −0.184055 (13) | 0.120663 (12) | 0.329974 (7) | 0.01335 (3) | |
Ru3 | −0.006333 (14) | 0.260591 (12) | 0.267982 (7) | 0.01472 (3) | |
As1 | 0.174870 (18) | 0.346910 (16) | 0.217792 (10) | 0.01513 (4) | |
P1 | −0.14945 (4) | −0.15583 (4) | 0.26340 (2) | 0.01517 (8) | |
P2 | −0.32726 (4) | −0.04886 (4) | 0.33226 (2) | 0.01405 (8) | |
O1 | −0.35304 (14) | 0.02944 (13) | 0.14079 (7) | 0.0228 (3) | |
O2 | −0.01281 (17) | −0.06563 (15) | 0.10257 (8) | 0.0307 (4) | |
O3 | 0.18160 (14) | 0.06485 (14) | 0.30313 (8) | 0.0233 (3) | |
O4 | 0.01850 (14) | 0.02577 (14) | 0.42259 (8) | 0.0251 (3) | |
O5 | −0.22301 (17) | 0.26804 (15) | 0.44509 (8) | 0.0322 (4) | |
O6 | −0.36138 (14) | 0.23945 (13) | 0.23654 (8) | 0.0244 (3) | |
O7 | 0.16295 (16) | 0.27361 (15) | 0.41018 (8) | 0.0313 (4) | |
O8 | −0.09867 (17) | 0.45777 (14) | 0.31728 (9) | 0.0318 (4) | |
O9 | −0.17955 (16) | 0.26067 (15) | 0.12914 (8) | 0.0285 (3) | |
C1 | −0.01915 (18) | −0.21580 (16) | 0.30540 (10) | 0.0184 (3) | |
C2 | 0.0805 (2) | −0.21172 (19) | 0.27234 (12) | 0.0241 (4) | |
H2A | 0.0810 | −0.1756 | 0.2321 | 0.029* | |
C3 | 0.1795 (2) | −0.2612 (2) | 0.29890 (13) | 0.0279 (4) | |
H3A | 0.2453 | −0.2584 | 0.2762 | 0.033* | |
C4 | 0.1805 (2) | −0.3145 (2) | 0.35887 (12) | 0.0277 (4) | |
H4A | 0.2462 | −0.3484 | 0.3761 | 0.033* | |
C5 | 0.0834 (2) | −0.3173 (2) | 0.39312 (12) | 0.0272 (4) | |
H5A | 0.0844 | −0.3522 | 0.4338 | 0.033* | |
C6 | −0.0160 (2) | −0.26779 (19) | 0.36655 (11) | 0.0239 (4) | |
H6A | −0.0808 | −0.2695 | 0.3899 | 0.029* | |
C7 | −0.23405 (18) | −0.27244 (16) | 0.19979 (10) | 0.0189 (3) | |
C8 | −0.2579 (2) | −0.38311 (18) | 0.22004 (12) | 0.0256 (4) | |
H8A | −0.2311 | −0.3969 | 0.2652 | 0.031* | |
C9 | −0.3213 (3) | −0.4723 (2) | 0.17321 (14) | 0.0357 (5) | |
H9A | −0.3373 | −0.5455 | 0.1871 | 0.043* | |
C10 | −0.3608 (3) | −0.4528 (2) | 0.10588 (15) | 0.0389 (6) | |
H10A | −0.4030 | −0.5128 | 0.0746 | 0.047* | |
C11 | −0.3375 (2) | −0.3440 (2) | 0.08499 (13) | 0.0323 (5) | |
H11A | −0.3639 | −0.3310 | 0.0397 | 0.039* | |
C12 | −0.2743 (2) | −0.25394 (18) | 0.13192 (11) | 0.0236 (4) | |
H12A | −0.2590 | −0.1809 | 0.1177 | 0.028* | |
C13 | −0.25005 (17) | −0.16738 (16) | 0.32744 (10) | 0.0169 (3) | |
H13A | −0.3142 | −0.2368 | 0.3169 | 0.020* | |
H13B | −0.1990 | −0.1724 | 0.3717 | 0.020* | |
C14 | −0.38444 (17) | −0.07840 (16) | 0.41085 (9) | 0.0165 (3) | |
C15 | −0.29807 (19) | −0.0528 (2) | 0.47252 (10) | 0.0236 (4) | |
H15A | −0.2149 | −0.0177 | 0.4728 | 0.028* | |
C16 | −0.3348 (2) | −0.0791 (2) | 0.53344 (11) | 0.0268 (4) | |
H16A | −0.2764 | −0.0623 | 0.5742 | 0.032* | |
C17 | −0.4591 (2) | −0.13053 (19) | 0.53333 (11) | 0.0248 (4) | |
H17A | −0.4841 | −0.1481 | 0.5741 | 0.030* | |
C18 | −0.5454 (2) | −0.15564 (19) | 0.47262 (11) | 0.0247 (4) | |
H18A | −0.6286 | −0.1899 | 0.4726 | 0.030* | |
C19 | −0.50858 (19) | −0.12991 (17) | 0.41136 (10) | 0.0206 (4) | |
H19A | −0.5672 | −0.1472 | 0.3707 | 0.025* | |
C20 | −0.46895 (16) | −0.08207 (16) | 0.26597 (9) | 0.0155 (3) | |
C21 | −0.54723 (17) | −0.00499 (16) | 0.25740 (9) | 0.0169 (3) | |
H21A | −0.5280 | 0.0595 | 0.2867 | 0.020* | |
C22 | −0.65329 (18) | −0.02445 (18) | 0.20536 (10) | 0.0206 (4) | |
H22A | −0.7048 | 0.0269 | 0.2000 | 0.025* | |
C23 | −0.68229 (19) | −0.1205 (2) | 0.16137 (11) | 0.0242 (4) | |
H23A | −0.7524 | −0.1328 | 0.1261 | 0.029* | |
C24 | −0.6067 (2) | −0.19810 (19) | 0.17000 (11) | 0.0241 (4) | |
H24A | −0.6269 | −0.2629 | 0.1409 | 0.029* | |
C25 | −0.50038 (18) | −0.17913 (17) | 0.22222 (10) | 0.0196 (3) | |
H25A | −0.4502 | −0.2316 | 0.2279 | 0.024* | |
C26 | 0.14521 (18) | 0.46556 (16) | 0.15728 (10) | 0.0175 (3) | |
C27 | 0.0521 (2) | 0.52311 (18) | 0.16335 (11) | 0.0230 (4) | |
H27A | 0.0087 | 0.5090 | 0.1985 | 0.028* | |
C28 | 0.0236 (2) | 0.60180 (19) | 0.11705 (11) | 0.0257 (4) | |
H28A | −0.0388 | 0.6397 | 0.1218 | 0.031* | |
C29 | 0.0867 (2) | 0.62468 (17) | 0.06387 (10) | 0.0224 (4) | |
C30 | 0.1811 (2) | 0.56661 (19) | 0.05844 (11) | 0.0253 (4) | |
H30A | 0.2248 | 0.5806 | 0.0233 | 0.030* | |
C31 | 0.2101 (2) | 0.48899 (18) | 0.10459 (11) | 0.0221 (4) | |
H31A | 0.2735 | 0.4520 | 0.1004 | 0.027* | |
C32 | 0.32589 (17) | 0.41783 (16) | 0.28350 (10) | 0.0178 (3) | |
C33 | 0.37183 (18) | 0.53379 (17) | 0.28934 (10) | 0.0201 (3) | |
H33A | 0.3344 | 0.5787 | 0.2588 | 0.024* | |
C34 | 0.4737 (2) | 0.58329 (18) | 0.34080 (12) | 0.0249 (4) | |
H34A | 0.5024 | 0.6613 | 0.3447 | 0.030* | |
C35 | 0.5331 (2) | 0.5188 (2) | 0.38627 (12) | 0.0282 (4) | |
C36 | 0.4884 (2) | 0.4020 (2) | 0.37915 (13) | 0.0323 (5) | |
H36A | 0.5283 | 0.3571 | 0.4087 | 0.039* | |
C37 | 0.3853 (2) | 0.35127 (19) | 0.32867 (12) | 0.0271 (4) | |
H37A | 0.3560 | 0.2733 | 0.3250 | 0.032* | |
C38 | 0.24235 (18) | 0.25781 (16) | 0.15858 (10) | 0.0180 (3) | |
C39 | 0.37055 (19) | 0.27305 (19) | 0.16030 (11) | 0.0228 (4) | |
H39A | 0.4281 | 0.3234 | 0.1930 | 0.027* | |
C40 | 0.4128 (2) | 0.2133 (2) | 0.11325 (11) | 0.0270 (4) | |
H40A | 0.4987 | 0.2243 | 0.1147 | 0.032* | |
C41 | 0.3282 (2) | 0.1367 (2) | 0.06356 (11) | 0.0259 (4) | |
C42 | 0.2006 (2) | 0.12344 (19) | 0.06198 (10) | 0.0248 (4) | |
H42A | 0.1430 | 0.0737 | 0.0290 | 0.030* | |
C43 | 0.1574 (2) | 0.18324 (18) | 0.10882 (10) | 0.0208 (4) | |
H43A | 0.0715 | 0.1733 | 0.1068 | 0.025* | |
C44 | 0.07788 (19) | 0.05990 (17) | 0.27751 (10) | 0.0193 (3) | |
C45 | −0.03974 (19) | −0.02775 (18) | 0.14906 (10) | 0.0205 (3) | |
C46 | −0.25780 (19) | 0.02840 (16) | 0.17457 (10) | 0.0180 (3) | |
C47 | −0.29468 (18) | 0.19138 (16) | 0.26811 (9) | 0.0173 (3) | |
C48 | −0.20782 (18) | 0.21153 (18) | 0.40222 (10) | 0.0199 (3) | |
C49 | −0.05406 (18) | 0.06182 (17) | 0.38594 (10) | 0.0186 (3) | |
C50 | 0.0998 (2) | 0.26239 (17) | 0.35718 (10) | 0.0210 (4) | |
C51 | −0.05753 (19) | 0.38722 (17) | 0.29861 (10) | 0.0208 (4) | |
C52 | −0.11750 (19) | 0.25061 (18) | 0.18030 (10) | 0.0208 (4) | |
C53 | 0.0546 (3) | 0.7065 (2) | 0.01282 (11) | 0.0315 (5) | |
H53A | −0.0010 | 0.7474 | 0.0280 | 0.047* | |
H53B | 0.0140 | 0.6662 | −0.0301 | 0.047* | |
H53C | 0.1301 | 0.7584 | 0.0078 | 0.047* | |
C54 | 0.6437 (3) | 0.5730 (3) | 0.44273 (15) | 0.0442 (7) | |
H54A | 0.6470 | 0.6523 | 0.4484 | 0.066* | |
H54B | 0.7203 | 0.5625 | 0.4310 | 0.066* | |
H54C | 0.6336 | 0.5386 | 0.4844 | 0.066* | |
C55 | 0.3739 (3) | 0.0679 (3) | 0.01549 (12) | 0.0391 (6) | |
H55A | 0.3033 | 0.0187 | −0.0137 | 0.059* | |
H55B | 0.4264 | 0.0237 | 0.0408 | 0.059* | |
H55C | 0.4215 | 0.1170 | −0.0115 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.01525 (6) | 0.01428 (6) | 0.01282 (6) | 0.00304 (5) | 0.00261 (4) | 0.00064 (5) |
Ru2 | 0.01196 (6) | 0.01505 (6) | 0.01221 (5) | 0.00194 (5) | 0.00173 (4) | 0.00064 (4) |
Ru3 | 0.01490 (6) | 0.01372 (6) | 0.01460 (6) | 0.00119 (5) | 0.00306 (5) | 0.00016 (5) |
As1 | 0.01466 (8) | 0.01405 (8) | 0.01656 (8) | 0.00346 (6) | 0.00254 (6) | 0.00169 (6) |
P1 | 0.01332 (19) | 0.0149 (2) | 0.0173 (2) | 0.00427 (16) | 0.00200 (15) | 0.00145 (16) |
P2 | 0.01206 (18) | 0.0156 (2) | 0.01410 (18) | 0.00291 (15) | 0.00175 (14) | 0.00185 (15) |
O1 | 0.0227 (7) | 0.0262 (7) | 0.0189 (6) | 0.0075 (6) | 0.0004 (5) | −0.0001 (5) |
O2 | 0.0337 (9) | 0.0331 (9) | 0.0253 (8) | 0.0052 (7) | 0.0099 (7) | −0.0068 (7) |
O3 | 0.0183 (6) | 0.0279 (8) | 0.0228 (7) | 0.0055 (6) | 0.0020 (5) | −0.0028 (6) |
O4 | 0.0177 (6) | 0.0336 (8) | 0.0233 (7) | 0.0063 (6) | 0.0012 (5) | 0.0080 (6) |
O5 | 0.0380 (9) | 0.0348 (9) | 0.0240 (7) | 0.0046 (7) | 0.0115 (7) | −0.0070 (7) |
O6 | 0.0212 (7) | 0.0253 (7) | 0.0269 (7) | 0.0076 (6) | 0.0016 (6) | 0.0072 (6) |
O7 | 0.0311 (8) | 0.0325 (9) | 0.0236 (7) | 0.0011 (7) | −0.0040 (6) | 0.0019 (6) |
O8 | 0.0375 (9) | 0.0248 (8) | 0.0358 (9) | 0.0107 (7) | 0.0098 (7) | −0.0001 (7) |
O9 | 0.0288 (8) | 0.0299 (8) | 0.0224 (7) | 0.0011 (7) | 0.0003 (6) | 0.0072 (6) |
C1 | 0.0150 (7) | 0.0170 (8) | 0.0227 (8) | 0.0049 (6) | 0.0013 (6) | 0.0013 (7) |
C2 | 0.0207 (9) | 0.0261 (10) | 0.0280 (10) | 0.0087 (8) | 0.0067 (7) | 0.0055 (8) |
C3 | 0.0193 (9) | 0.0308 (11) | 0.0361 (12) | 0.0104 (8) | 0.0065 (8) | 0.0042 (9) |
C4 | 0.0185 (9) | 0.0279 (11) | 0.0356 (11) | 0.0094 (8) | −0.0014 (8) | 0.0015 (9) |
C5 | 0.0268 (10) | 0.0284 (11) | 0.0265 (10) | 0.0115 (9) | −0.0008 (8) | 0.0041 (8) |
C6 | 0.0209 (9) | 0.0281 (10) | 0.0238 (9) | 0.0106 (8) | 0.0013 (7) | 0.0040 (8) |
C7 | 0.0163 (8) | 0.0167 (8) | 0.0238 (9) | 0.0058 (6) | 0.0021 (6) | −0.0015 (7) |
C8 | 0.0274 (10) | 0.0167 (9) | 0.0314 (11) | 0.0045 (8) | 0.0031 (8) | 0.0017 (8) |
C9 | 0.0410 (14) | 0.0175 (10) | 0.0435 (14) | 0.0022 (9) | 0.0018 (11) | −0.0011 (9) |
C10 | 0.0448 (15) | 0.0226 (11) | 0.0407 (14) | 0.0023 (10) | −0.0047 (11) | −0.0102 (10) |
C11 | 0.0375 (13) | 0.0260 (11) | 0.0280 (11) | 0.0063 (10) | −0.0043 (9) | −0.0055 (9) |
C12 | 0.0246 (9) | 0.0185 (9) | 0.0253 (9) | 0.0045 (7) | 0.0002 (7) | −0.0025 (7) |
C13 | 0.0152 (7) | 0.0174 (8) | 0.0191 (8) | 0.0054 (6) | 0.0033 (6) | 0.0031 (6) |
C14 | 0.0158 (7) | 0.0179 (8) | 0.0172 (7) | 0.0055 (6) | 0.0047 (6) | 0.0046 (6) |
C15 | 0.0167 (8) | 0.0359 (11) | 0.0191 (8) | 0.0084 (8) | 0.0026 (6) | 0.0062 (8) |
C16 | 0.0265 (10) | 0.0383 (12) | 0.0176 (8) | 0.0112 (9) | 0.0046 (7) | 0.0083 (8) |
C17 | 0.0326 (11) | 0.0247 (10) | 0.0215 (9) | 0.0088 (8) | 0.0124 (8) | 0.0090 (8) |
C18 | 0.0262 (10) | 0.0230 (9) | 0.0256 (9) | 0.0003 (8) | 0.0122 (8) | 0.0035 (8) |
C19 | 0.0196 (8) | 0.0199 (9) | 0.0212 (8) | 0.0008 (7) | 0.0057 (7) | 0.0010 (7) |
C20 | 0.0131 (7) | 0.0167 (8) | 0.0157 (7) | 0.0022 (6) | 0.0017 (6) | 0.0025 (6) |
C21 | 0.0150 (7) | 0.0182 (8) | 0.0176 (7) | 0.0048 (6) | 0.0020 (6) | 0.0027 (6) |
C22 | 0.0164 (8) | 0.0252 (9) | 0.0208 (8) | 0.0071 (7) | 0.0021 (6) | 0.0065 (7) |
C23 | 0.0173 (8) | 0.0315 (11) | 0.0210 (9) | 0.0045 (8) | −0.0022 (7) | 0.0023 (8) |
C24 | 0.0210 (9) | 0.0243 (10) | 0.0229 (9) | 0.0023 (8) | −0.0016 (7) | −0.0052 (7) |
C25 | 0.0166 (8) | 0.0192 (8) | 0.0219 (8) | 0.0035 (7) | 0.0019 (6) | −0.0010 (7) |
C26 | 0.0174 (8) | 0.0158 (8) | 0.0183 (8) | 0.0033 (6) | 0.0015 (6) | 0.0024 (6) |
C27 | 0.0265 (10) | 0.0234 (9) | 0.0230 (9) | 0.0107 (8) | 0.0077 (7) | 0.0075 (7) |
C28 | 0.0289 (10) | 0.0249 (10) | 0.0268 (10) | 0.0127 (8) | 0.0056 (8) | 0.0081 (8) |
C29 | 0.0287 (10) | 0.0187 (9) | 0.0165 (8) | 0.0042 (7) | −0.0021 (7) | 0.0024 (7) |
C30 | 0.0327 (11) | 0.0222 (9) | 0.0210 (9) | 0.0036 (8) | 0.0076 (8) | 0.0057 (7) |
C31 | 0.0238 (9) | 0.0211 (9) | 0.0240 (9) | 0.0071 (7) | 0.0084 (7) | 0.0042 (7) |
C32 | 0.0156 (7) | 0.0184 (8) | 0.0183 (8) | 0.0019 (6) | 0.0026 (6) | 0.0011 (6) |
C33 | 0.0185 (8) | 0.0170 (8) | 0.0243 (9) | 0.0033 (7) | 0.0038 (7) | 0.0017 (7) |
C34 | 0.0213 (9) | 0.0192 (9) | 0.0306 (10) | −0.0015 (7) | 0.0040 (8) | −0.0017 (8) |
C35 | 0.0203 (9) | 0.0327 (11) | 0.0252 (10) | −0.0032 (8) | −0.0007 (7) | 0.0011 (8) |
C36 | 0.0276 (11) | 0.0299 (11) | 0.0317 (11) | 0.0007 (9) | −0.0069 (9) | 0.0093 (9) |
C37 | 0.0252 (10) | 0.0200 (9) | 0.0295 (10) | 0.0000 (8) | −0.0050 (8) | 0.0072 (8) |
C38 | 0.0197 (8) | 0.0170 (8) | 0.0187 (8) | 0.0073 (7) | 0.0038 (6) | 0.0019 (6) |
C39 | 0.0189 (8) | 0.0258 (10) | 0.0250 (9) | 0.0078 (7) | 0.0044 (7) | 0.0018 (8) |
C40 | 0.0238 (10) | 0.0378 (12) | 0.0233 (9) | 0.0136 (9) | 0.0066 (8) | 0.0047 (9) |
C41 | 0.0334 (11) | 0.0327 (11) | 0.0178 (8) | 0.0189 (9) | 0.0066 (8) | 0.0049 (8) |
C42 | 0.0313 (11) | 0.0266 (10) | 0.0170 (8) | 0.0097 (8) | 0.0023 (7) | 0.0020 (7) |
C43 | 0.0230 (9) | 0.0216 (9) | 0.0183 (8) | 0.0079 (7) | 0.0023 (7) | 0.0017 (7) |
C44 | 0.0207 (8) | 0.0199 (8) | 0.0160 (7) | 0.0011 (7) | 0.0046 (6) | −0.0010 (6) |
C45 | 0.0206 (8) | 0.0213 (9) | 0.0186 (8) | 0.0043 (7) | 0.0026 (6) | −0.0001 (7) |
C46 | 0.0219 (8) | 0.0158 (8) | 0.0169 (8) | 0.0048 (7) | 0.0047 (6) | 0.0007 (6) |
C47 | 0.0168 (8) | 0.0158 (8) | 0.0176 (8) | 0.0009 (6) | 0.0029 (6) | 0.0004 (6) |
C48 | 0.0187 (8) | 0.0226 (9) | 0.0177 (8) | 0.0028 (7) | 0.0042 (6) | 0.0013 (7) |
C49 | 0.0150 (7) | 0.0216 (9) | 0.0186 (8) | 0.0022 (7) | 0.0045 (6) | 0.0021 (7) |
C50 | 0.0224 (9) | 0.0174 (8) | 0.0218 (8) | 0.0017 (7) | 0.0043 (7) | 0.0017 (7) |
C51 | 0.0220 (9) | 0.0185 (8) | 0.0203 (8) | 0.0012 (7) | 0.0042 (7) | 0.0003 (7) |
C52 | 0.0189 (8) | 0.0214 (9) | 0.0208 (8) | 0.0009 (7) | 0.0051 (7) | 0.0026 (7) |
C53 | 0.0474 (14) | 0.0250 (10) | 0.0195 (9) | 0.0073 (10) | 0.0006 (9) | 0.0063 (8) |
C54 | 0.0340 (13) | 0.0455 (16) | 0.0374 (14) | −0.0084 (12) | −0.0116 (11) | 0.0021 (12) |
C55 | 0.0576 (17) | 0.0488 (16) | 0.0203 (10) | 0.0313 (14) | 0.0094 (10) | 0.0017 (10) |
Ru1—C45 | 1.891 (2) | C16—C17 | 1.388 (3) |
Ru1—C44 | 1.928 (2) | C16—H16A | 0.9300 |
Ru1—C46 | 1.942 (2) | C17—C18 | 1.381 (3) |
Ru1—P1 | 2.3190 (5) | C17—H17A | 0.9300 |
Ru1—Ru2 | 2.8338 (2) | C18—C19 | 1.392 (3) |
Ru1—Ru3 | 2.8890 (2) | C18—H18A | 0.9300 |
Ru2—C48 | 1.896 (2) | C19—H19A | 0.9300 |
Ru2—C47 | 1.9286 (19) | C20—C25 | 1.393 (3) |
Ru2—C49 | 1.931 (2) | C20—C21 | 1.404 (3) |
Ru2—P2 | 2.3253 (5) | C21—C22 | 1.390 (3) |
Ru2—Ru3 | 2.8208 (2) | C21—H21A | 0.9300 |
Ru3—C51 | 1.883 (2) | C22—C23 | 1.388 (3) |
Ru3—C52 | 1.932 (2) | C22—H22A | 0.9300 |
Ru3—C50 | 1.943 (2) | C23—C24 | 1.387 (3) |
Ru3—As1 | 2.4706 (2) | C23—H23A | 0.9300 |
As1—C32 | 1.9422 (19) | C24—C25 | 1.394 (3) |
As1—C38 | 1.9458 (19) | C24—H24A | 0.9300 |
As1—C26 | 1.9513 (19) | C25—H25A | 0.9300 |
P1—C1 | 1.8332 (19) | C26—C27 | 1.391 (3) |
P1—C7 | 1.844 (2) | C26—C31 | 1.394 (3) |
P1—C13 | 1.8503 (19) | C27—C28 | 1.394 (3) |
P2—C20 | 1.8193 (18) | C27—H27A | 0.9300 |
P2—C14 | 1.8283 (19) | C28—C29 | 1.390 (3) |
P2—C13 | 1.8402 (19) | C28—H28A | 0.9300 |
O1—C46 | 1.145 (2) | C29—C30 | 1.406 (3) |
O2—C45 | 1.149 (2) | C29—C53 | 1.494 (3) |
O3—C44 | 1.157 (2) | C30—C31 | 1.384 (3) |
O4—C49 | 1.151 (2) | C30—H30A | 0.9300 |
O5—C48 | 1.149 (3) | C31—H31A | 0.9300 |
O6—C47 | 1.148 (2) | C32—C33 | 1.387 (3) |
O7—C50 | 1.144 (3) | C32—C37 | 1.397 (3) |
O8—C51 | 1.143 (3) | C33—C34 | 1.392 (3) |
O9—C52 | 1.147 (3) | C33—H33A | 0.9300 |
C1—C2 | 1.390 (3) | C34—C35 | 1.383 (3) |
C1—C6 | 1.393 (3) | C34—H34A | 0.9300 |
C2—C3 | 1.391 (3) | C35—C36 | 1.394 (3) |
C2—H2A | 0.9300 | C35—C54 | 1.520 (3) |
C3—C4 | 1.381 (3) | C36—C37 | 1.393 (3) |
C3—H3A | 0.9300 | C36—H36A | 0.9300 |
C4—C5 | 1.383 (3) | C37—H37A | 0.9300 |
C4—H4A | 0.9300 | C38—C39 | 1.391 (3) |
C5—C6 | 1.395 (3) | C38—C43 | 1.392 (3) |
C5—H5A | 0.9300 | C39—C40 | 1.388 (3) |
C6—H6A | 0.9300 | C39—H39A | 0.9300 |
C7—C12 | 1.391 (3) | C40—C41 | 1.401 (3) |
C7—C8 | 1.401 (3) | C40—H40A | 0.9300 |
C8—C9 | 1.387 (3) | C41—C42 | 1.387 (3) |
C8—H8A | 0.9300 | C41—C55 | 1.492 (3) |
C9—C10 | 1.382 (4) | C42—C43 | 1.392 (3) |
C9—H9A | 0.9300 | C42—H42A | 0.9300 |
C10—C11 | 1.384 (4) | C43—H43A | 0.9300 |
C10—H10A | 0.9300 | C53—H53A | 0.9600 |
C11—C12 | 1.394 (3) | C53—H53B | 0.9600 |
C11—H11A | 0.9300 | C53—H53C | 0.9600 |
C12—H12A | 0.9300 | C54—H54A | 0.9600 |
C13—H13A | 0.9700 | C54—H54B | 0.9600 |
C13—H13B | 0.9700 | C54—H54C | 0.9600 |
C14—C19 | 1.390 (3) | C55—H55A | 0.9600 |
C14—C15 | 1.396 (3) | C55—H55B | 0.9600 |
C15—C16 | 1.386 (3) | C55—H55C | 0.9600 |
C15—H15A | 0.9300 | ||
C45—Ru1—C44 | 91.37 (8) | C15—C16—C17 | 119.8 (2) |
C45—Ru1—C46 | 93.46 (8) | C15—C16—H16A | 120.1 |
C44—Ru1—C46 | 165.13 (8) | C17—C16—H16A | 120.1 |
C45—Ru1—P1 | 94.42 (6) | C18—C17—C16 | 119.91 (19) |
C44—Ru1—P1 | 96.98 (6) | C18—C17—H17A | 120.0 |
C46—Ru1—P1 | 96.66 (6) | C16—C17—H17A | 120.0 |
C45—Ru1—Ru2 | 172.35 (6) | C17—C18—C19 | 120.4 (2) |
C44—Ru1—Ru2 | 92.49 (6) | C17—C18—H18A | 119.8 |
C46—Ru1—Ru2 | 81.22 (6) | C19—C18—H18A | 119.8 |
P1—Ru1—Ru2 | 91.664 (13) | C14—C19—C18 | 120.20 (19) |
C45—Ru1—Ru3 | 116.73 (6) | C14—C19—H19A | 119.9 |
C44—Ru1—Ru3 | 67.59 (6) | C18—C19—H19A | 119.9 |
C46—Ru1—Ru3 | 97.73 (6) | C25—C20—C21 | 118.95 (17) |
P1—Ru1—Ru3 | 144.599 (14) | C25—C20—P2 | 122.50 (14) |
Ru2—Ru1—Ru3 | 59.055 (5) | C21—C20—P2 | 118.52 (14) |
C48—Ru2—C47 | 88.44 (8) | C22—C21—C20 | 120.43 (18) |
C48—Ru2—C49 | 94.40 (8) | C22—C21—H21A | 119.8 |
C47—Ru2—C49 | 171.67 (8) | C20—C21—H21A | 119.8 |
C48—Ru2—P2 | 103.24 (6) | C23—C22—C21 | 120.03 (19) |
C47—Ru2—P2 | 97.15 (6) | C23—C22—H22A | 120.0 |
C49—Ru2—P2 | 89.84 (6) | C21—C22—H22A | 120.0 |
C48—Ru2—Ru3 | 105.92 (6) | C24—C23—C22 | 120.04 (19) |
C47—Ru2—Ru3 | 80.25 (6) | C24—C23—H23A | 120.0 |
C49—Ru2—Ru3 | 91.43 (6) | C22—C23—H23A | 120.0 |
P2—Ru2—Ru3 | 150.627 (13) | C23—C24—C25 | 120.16 (19) |
C48—Ru2—Ru1 | 166.17 (6) | C23—C24—H24A | 119.9 |
C47—Ru2—Ru1 | 94.46 (6) | C25—C24—H24A | 119.9 |
C49—Ru2—Ru1 | 80.97 (6) | C20—C25—C24 | 120.38 (19) |
P2—Ru2—Ru1 | 89.842 (13) | C20—C25—H25A | 119.8 |
Ru3—Ru2—Ru1 | 61.448 (5) | C24—C25—H25A | 119.8 |
C51—Ru3—C52 | 92.34 (9) | C27—C26—C31 | 118.77 (18) |
C51—Ru3—C50 | 89.02 (9) | C27—C26—As1 | 120.03 (15) |
C52—Ru3—C50 | 176.73 (8) | C31—C26—As1 | 121.06 (15) |
C51—Ru3—As1 | 102.66 (6) | C26—C27—C28 | 120.5 (2) |
C52—Ru3—As1 | 90.29 (6) | C26—C27—H27A | 119.8 |
C50—Ru3—As1 | 92.32 (6) | C28—C27—H27A | 119.8 |
C51—Ru3—Ru2 | 89.27 (6) | C29—C28—C27 | 121.2 (2) |
C52—Ru3—Ru2 | 95.19 (6) | C29—C28—H28A | 119.4 |
C50—Ru3—Ru2 | 81.84 (6) | C27—C28—H28A | 119.4 |
As1—Ru3—Ru2 | 166.672 (9) | C28—C29—C30 | 117.92 (19) |
C51—Ru3—Ru1 | 143.34 (6) | C28—C29—C53 | 121.7 (2) |
C52—Ru3—Ru1 | 73.64 (6) | C30—C29—C53 | 120.4 (2) |
C50—Ru3—Ru1 | 103.55 (6) | C31—C30—C29 | 120.9 (2) |
As1—Ru3—Ru1 | 110.910 (8) | C31—C30—H30A | 119.5 |
Ru2—Ru3—Ru1 | 59.496 (5) | C29—C30—H30A | 119.5 |
C32—As1—C38 | 101.24 (8) | C30—C31—C26 | 120.7 (2) |
C32—As1—C26 | 104.04 (8) | C30—C31—H31A | 119.6 |
C38—As1—C26 | 98.60 (8) | C26—C31—H31A | 119.6 |
C32—As1—Ru3 | 114.70 (6) | C33—C32—C37 | 119.16 (18) |
C38—As1—Ru3 | 121.17 (6) | C33—C32—As1 | 121.50 (15) |
C26—As1—Ru3 | 114.49 (6) | C37—C32—As1 | 119.23 (15) |
C1—P1—C7 | 100.13 (9) | C32—C33—C34 | 120.27 (19) |
C1—P1—C13 | 102.22 (9) | C32—C33—H33A | 119.9 |
C7—P1—C13 | 102.95 (9) | C34—C33—H33A | 119.9 |
C1—P1—Ru1 | 115.63 (6) | C35—C34—C33 | 121.3 (2) |
C7—P1—Ru1 | 118.28 (7) | C35—C34—H34A | 119.3 |
C13—P1—Ru1 | 115.20 (6) | C33—C34—H34A | 119.3 |
C20—P2—C14 | 104.13 (8) | C34—C35—C36 | 118.2 (2) |
C20—P2—C13 | 105.86 (9) | C34—C35—C54 | 121.3 (2) |
C14—P2—C13 | 99.07 (9) | C36—C35—C54 | 120.6 (2) |
C20—P2—Ru2 | 117.91 (6) | C37—C36—C35 | 121.2 (2) |
C14—P2—Ru2 | 117.92 (6) | C37—C36—H36A | 119.4 |
C13—P2—Ru2 | 109.76 (6) | C35—C36—H36A | 119.4 |
C2—C1—C6 | 118.60 (18) | C36—C37—C32 | 119.8 (2) |
C2—C1—P1 | 117.10 (15) | C36—C37—H37A | 120.1 |
C6—C1—P1 | 124.27 (15) | C32—C37—H37A | 120.1 |
C1—C2—C3 | 120.6 (2) | C39—C38—C43 | 119.29 (18) |
C1—C2—H2A | 119.7 | C39—C38—As1 | 122.65 (15) |
C3—C2—H2A | 119.7 | C43—C38—As1 | 117.81 (15) |
C4—C3—C2 | 120.3 (2) | C40—C39—C38 | 120.1 (2) |
C4—C3—H3A | 119.8 | C40—C39—H39A | 119.9 |
C2—C3—H3A | 119.8 | C38—C39—H39A | 119.9 |
C3—C4—C5 | 119.8 (2) | C39—C40—C41 | 121.1 (2) |
C3—C4—H4A | 120.1 | C39—C40—H40A | 119.4 |
C5—C4—H4A | 120.1 | C41—C40—H40A | 119.4 |
C4—C5—C6 | 120.0 (2) | C42—C41—C40 | 118.1 (2) |
C4—C5—H5A | 120.0 | C42—C41—C55 | 120.8 (2) |
C6—C5—H5A | 120.0 | C40—C41—C55 | 121.0 (2) |
C1—C6—C5 | 120.7 (2) | C41—C42—C43 | 121.2 (2) |
C1—C6—H6A | 119.7 | C41—C42—H42A | 119.4 |
C5—C6—H6A | 119.7 | C43—C42—H42A | 119.4 |
C12—C7—C8 | 118.79 (19) | C38—C43—C42 | 120.17 (19) |
C12—C7—P1 | 121.89 (15) | C38—C43—H43A | 119.9 |
C8—C7—P1 | 119.32 (16) | C42—C43—H43A | 119.9 |
C9—C8—C7 | 120.5 (2) | O3—C44—Ru1 | 168.27 (18) |
C9—C8—H8A | 119.8 | O2—C45—Ru1 | 175.42 (19) |
C7—C8—H8A | 119.8 | O1—C46—Ru1 | 175.83 (17) |
C10—C9—C8 | 120.1 (2) | O6—C47—Ru2 | 173.52 (17) |
C10—C9—H9A | 119.9 | O5—C48—Ru2 | 178.6 (2) |
C8—C9—H9A | 119.9 | O4—C49—Ru2 | 175.36 (17) |
C9—C10—C11 | 120.1 (2) | O7—C50—Ru3 | 173.88 (19) |
C9—C10—H10A | 119.9 | O8—C51—Ru3 | 173.89 (19) |
C11—C10—H10A | 119.9 | O9—C52—Ru3 | 170.53 (19) |
C10—C11—C12 | 120.0 (2) | C29—C53—H53A | 109.5 |
C10—C11—H11A | 120.0 | C29—C53—H53B | 109.5 |
C12—C11—H11A | 120.0 | H53A—C53—H53B | 109.5 |
C7—C12—C11 | 120.5 (2) | C29—C53—H53C | 109.5 |
C7—C12—H12A | 119.8 | H53A—C53—H53C | 109.5 |
C11—C12—H12A | 119.8 | H53B—C53—H53C | 109.5 |
P2—C13—P1 | 114.18 (10) | C35—C54—H54A | 109.5 |
P2—C13—H13A | 108.7 | C35—C54—H54B | 109.5 |
P1—C13—H13A | 108.7 | H54A—C54—H54B | 109.5 |
P2—C13—H13B | 108.7 | C35—C54—H54C | 109.5 |
P1—C13—H13B | 108.7 | H54A—C54—H54C | 109.5 |
H13A—C13—H13B | 107.6 | H54B—C54—H54C | 109.5 |
C19—C14—C15 | 118.95 (18) | C41—C55—H55A | 109.5 |
C19—C14—P2 | 122.70 (15) | C41—C55—H55B | 109.5 |
C15—C14—P2 | 118.28 (14) | H55A—C55—H55B | 109.5 |
C16—C15—C14 | 120.74 (19) | C41—C55—H55C | 109.5 |
C16—C15—H15A | 119.6 | H55A—C55—H55C | 109.5 |
C14—C15—H15A | 119.6 | H55B—C55—H55C | 109.5 |
C44—Ru1—Ru2—C48 | 36.6 (3) | Ru1—P1—C1—C2 | −49.09 (18) |
C46—Ru1—Ru2—C48 | −129.9 (3) | C7—P1—C1—C6 | −98.64 (19) |
P1—Ru1—Ru2—C48 | 133.7 (3) | C13—P1—C1—C6 | 7.1 (2) |
Ru3—Ru1—Ru2—C48 | −25.3 (3) | Ru1—P1—C1—C6 | 133.08 (17) |
C44—Ru1—Ru2—C47 | 138.26 (8) | C6—C1—C2—C3 | 1.7 (3) |
C46—Ru1—Ru2—C47 | −28.19 (8) | P1—C1—C2—C3 | −176.25 (18) |
P1—Ru1—Ru2—C47 | −124.67 (6) | C1—C2—C3—C4 | −0.5 (4) |
Ru3—Ru1—Ru2—C47 | 76.36 (5) | C2—C3—C4—C5 | −0.9 (4) |
C44—Ru1—Ru2—C49 | −34.71 (8) | C3—C4—C5—C6 | 0.9 (4) |
C46—Ru1—Ru2—C49 | 158.83 (8) | C2—C1—C6—C5 | −1.7 (3) |
P1—Ru1—Ru2—C49 | 62.35 (6) | P1—C1—C6—C5 | 176.15 (17) |
Ru3—Ru1—Ru2—C49 | −96.62 (6) | C4—C5—C6—C1 | 0.4 (3) |
C44—Ru1—Ru2—P2 | −124.58 (6) | C1—P1—C7—C12 | −132.65 (18) |
C46—Ru1—Ru2—P2 | 68.96 (6) | C13—P1—C7—C12 | 122.18 (18) |
P1—Ru1—Ru2—P2 | −27.517 (17) | Ru1—P1—C7—C12 | −6.1 (2) |
Ru3—Ru1—Ru2—P2 | 173.516 (13) | C1—P1—C7—C8 | 46.89 (18) |
C44—Ru1—Ru2—Ru3 | 61.90 (6) | C13—P1—C7—C8 | −58.28 (18) |
C46—Ru1—Ru2—Ru3 | −104.55 (6) | Ru1—P1—C7—C8 | 173.41 (14) |
P1—Ru1—Ru2—Ru3 | 158.967 (13) | C12—C7—C8—C9 | −0.4 (3) |
C48—Ru2—Ru3—C51 | −26.27 (9) | P1—C7—C8—C9 | −179.98 (19) |
C47—Ru2—Ru3—C51 | 59.27 (8) | C7—C8—C9—C10 | 0.5 (4) |
C49—Ru2—Ru3—C51 | −121.25 (9) | C8—C9—C10—C11 | −0.2 (4) |
P2—Ru2—Ru3—C51 | 146.53 (7) | C9—C10—C11—C12 | −0.1 (4) |
Ru1—Ru2—Ru3—C51 | 159.84 (6) | C8—C7—C12—C11 | 0.1 (3) |
C48—Ru2—Ru3—C52 | −118.55 (9) | P1—C7—C12—C11 | 179.64 (18) |
C47—Ru2—Ru3—C52 | −33.01 (9) | C10—C11—C12—C7 | 0.2 (4) |
C49—Ru2—Ru3—C52 | 146.47 (9) | C20—P2—C13—P1 | 84.11 (11) |
P2—Ru2—Ru3—C52 | 54.24 (7) | C14—P2—C13—P1 | −168.29 (10) |
Ru1—Ru2—Ru3—C52 | 67.55 (6) | Ru2—P2—C13—P1 | −44.14 (11) |
C48—Ru2—Ru3—C50 | 62.84 (9) | C1—P1—C13—P2 | 143.73 (10) |
C47—Ru2—Ru3—C50 | 148.38 (9) | C7—P1—C13—P2 | −112.71 (11) |
C49—Ru2—Ru3—C50 | −32.14 (9) | Ru1—P1—C13—P2 | 17.50 (12) |
P2—Ru2—Ru3—C50 | −124.36 (7) | C20—P2—C14—C19 | 7.93 (19) |
Ru1—Ru2—Ru3—C50 | −111.05 (6) | C13—P2—C14—C19 | −101.07 (18) |
C48—Ru2—Ru3—As1 | 127.52 (7) | Ru2—P2—C14—C19 | 140.75 (15) |
C47—Ru2—Ru3—As1 | −146.94 (7) | C20—P2—C14—C15 | −175.16 (17) |
C49—Ru2—Ru3—As1 | 32.54 (7) | C13—P2—C14—C15 | 75.84 (18) |
P2—Ru2—Ru3—As1 | −59.69 (5) | Ru2—P2—C14—C15 | −42.34 (19) |
Ru1—Ru2—Ru3—As1 | −46.38 (3) | C19—C14—C15—C16 | 0.6 (3) |
C48—Ru2—Ru3—Ru1 | 173.90 (6) | P2—C14—C15—C16 | −176.45 (18) |
C47—Ru2—Ru3—Ru1 | −100.56 (6) | C14—C15—C16—C17 | −0.6 (4) |
C49—Ru2—Ru3—Ru1 | 78.91 (6) | C15—C16—C17—C18 | 0.2 (4) |
P2—Ru2—Ru3—Ru1 | −13.31 (3) | C16—C17—C18—C19 | 0.2 (3) |
C45—Ru1—Ru3—C51 | 137.45 (12) | C15—C14—C19—C18 | −0.2 (3) |
C44—Ru1—Ru3—C51 | −142.84 (12) | P2—C14—C19—C18 | 176.67 (16) |
C46—Ru1—Ru3—C51 | 39.61 (12) | C17—C18—C19—C14 | −0.1 (3) |
P1—Ru1—Ru3—C51 | −73.53 (11) | C14—P2—C20—C25 | −105.57 (17) |
Ru2—Ru1—Ru3—C51 | −35.26 (10) | C13—P2—C20—C25 | −1.66 (18) |
C45—Ru1—Ru3—C52 | 66.31 (9) | Ru2—P2—C20—C25 | 121.60 (15) |
C44—Ru1—Ru3—C52 | 146.02 (9) | C14—P2—C20—C21 | 76.48 (16) |
C46—Ru1—Ru3—C52 | −31.53 (8) | C13—P2—C20—C21 | −179.60 (14) |
P1—Ru1—Ru3—C52 | −144.67 (7) | Ru2—P2—C20—C21 | −56.35 (16) |
Ru2—Ru1—Ru3—C52 | −106.40 (6) | C25—C20—C21—C22 | −1.0 (3) |
C45—Ru1—Ru3—C50 | −115.43 (9) | P2—C20—C21—C22 | 177.00 (15) |
C44—Ru1—Ru3—C50 | −35.72 (9) | C20—C21—C22—C23 | −0.1 (3) |
C46—Ru1—Ru3—C50 | 146.72 (8) | C21—C22—C23—C24 | 1.1 (3) |
P1—Ru1—Ru3—C50 | 33.59 (7) | C22—C23—C24—C25 | −0.9 (3) |
Ru2—Ru1—Ru3—C50 | 71.85 (6) | C21—C20—C25—C24 | 1.2 (3) |
C45—Ru1—Ru3—As1 | −17.57 (7) | P2—C20—C25—C24 | −176.75 (16) |
C44—Ru1—Ru3—As1 | 62.13 (6) | C23—C24—C25—C20 | −0.2 (3) |
C46—Ru1—Ru3—As1 | −115.42 (6) | C32—As1—C26—C27 | −102.95 (17) |
P1—Ru1—Ru3—As1 | 131.45 (2) | C38—As1—C26—C27 | 153.10 (17) |
Ru2—Ru1—Ru3—As1 | 169.709 (9) | Ru3—As1—C26—C27 | 23.01 (18) |
C45—Ru1—Ru3—Ru2 | 172.72 (7) | C32—As1—C26—C31 | 81.46 (17) |
C44—Ru1—Ru3—Ru2 | −107.58 (6) | C38—As1—C26—C31 | −22.49 (18) |
C46—Ru1—Ru3—Ru2 | 74.87 (6) | Ru3—As1—C26—C31 | −152.58 (15) |
P1—Ru1—Ru3—Ru2 | −38.26 (2) | C31—C26—C27—C28 | 0.7 (3) |
C51—Ru3—As1—C32 | 72.96 (9) | As1—C26—C27—C28 | −174.99 (17) |
C52—Ru3—As1—C32 | 165.42 (9) | C26—C27—C28—C29 | 0.1 (3) |
C50—Ru3—As1—C32 | −16.55 (9) | C27—C28—C29—C30 | −0.5 (3) |
Ru2—Ru3—As1—C32 | −80.12 (7) | C27—C28—C29—C53 | 178.3 (2) |
Ru1—Ru3—As1—C32 | −122.01 (7) | C28—C29—C30—C31 | 0.1 (3) |
C51—Ru3—As1—C38 | −165.10 (9) | C53—C29—C30—C31 | −178.7 (2) |
C52—Ru3—As1—C38 | −72.64 (9) | C29—C30—C31—C26 | 0.7 (3) |
C50—Ru3—As1—C38 | 105.38 (9) | C27—C26—C31—C30 | −1.1 (3) |
Ru2—Ru3—As1—C38 | 41.81 (8) | As1—C26—C31—C30 | 174.55 (16) |
Ru1—Ru3—As1—C38 | −0.08 (7) | C38—As1—C32—C33 | 115.60 (17) |
C51—Ru3—As1—C26 | −47.24 (9) | C26—As1—C32—C33 | 13.66 (18) |
C52—Ru3—As1—C26 | 45.23 (9) | Ru3—As1—C32—C33 | −112.16 (15) |
C50—Ru3—As1—C26 | −136.75 (9) | C38—As1—C32—C37 | −68.31 (18) |
Ru2—Ru3—As1—C26 | 159.68 (7) | C26—As1—C32—C37 | −170.24 (17) |
Ru1—Ru3—As1—C26 | 117.79 (6) | Ru3—As1—C32—C37 | 63.93 (18) |
C45—Ru1—P1—C1 | 76.59 (10) | C37—C32—C33—C34 | −1.8 (3) |
C44—Ru1—P1—C1 | −15.33 (9) | As1—C32—C33—C34 | 174.32 (16) |
C46—Ru1—P1—C1 | 170.60 (9) | C32—C33—C34—C35 | 1.3 (3) |
Ru2—Ru1—P1—C1 | −108.04 (7) | C33—C34—C35—C36 | 0.3 (4) |
Ru3—Ru1—P1—C1 | −75.95 (8) | C33—C34—C35—C54 | −179.6 (2) |
C45—Ru1—P1—C7 | −42.07 (9) | C34—C35—C36—C37 | −1.4 (4) |
C44—Ru1—P1—C7 | −134.00 (9) | C54—C35—C36—C37 | 178.5 (3) |
C46—Ru1—P1—C7 | 51.94 (9) | C35—C36—C37—C32 | 0.9 (4) |
Ru2—Ru1—P1—C7 | 133.29 (7) | C33—C32—C37—C36 | 0.7 (3) |
Ru3—Ru1—P1—C7 | 165.39 (7) | As1—C32—C37—C36 | −175.50 (19) |
C45—Ru1—P1—C13 | −164.38 (9) | C32—As1—C38—C39 | −13.32 (19) |
C44—Ru1—P1—C13 | 103.69 (9) | C26—As1—C38—C39 | 92.96 (18) |
C46—Ru1—P1—C13 | −70.37 (9) | Ru3—As1—C38—C39 | −141.50 (15) |
Ru2—Ru1—P1—C13 | 10.98 (7) | C32—As1—C38—C43 | 172.46 (15) |
Ru3—Ru1—P1—C13 | 43.08 (7) | C26—As1—C38—C43 | −81.27 (16) |
C48—Ru2—P2—C20 | 105.96 (9) | Ru3—As1—C38—C43 | 44.27 (17) |
C47—Ru2—P2—C20 | 15.89 (9) | C43—C38—C39—C40 | −0.8 (3) |
C49—Ru2—P2—C20 | −159.56 (9) | As1—C38—C39—C40 | −174.90 (17) |
Ru3—Ru2—P2—C20 | −66.91 (8) | C38—C39—C40—C41 | −0.2 (3) |
Ru1—Ru2—P2—C20 | −78.58 (7) | C39—C40—C41—C42 | 1.0 (3) |
C48—Ru2—P2—C14 | −20.44 (9) | C39—C40—C41—C55 | −176.6 (2) |
C47—Ru2—P2—C14 | −110.51 (9) | C40—C41—C42—C43 | −0.8 (3) |
C49—Ru2—P2—C14 | 74.04 (9) | C55—C41—C42—C43 | 176.8 (2) |
Ru3—Ru2—P2—C14 | 166.69 (7) | C39—C38—C43—C42 | 0.9 (3) |
Ru1—Ru2—P2—C14 | 155.02 (7) | As1—C38—C43—C42 | 175.37 (16) |
C48—Ru2—P2—C13 | −132.77 (9) | C41—C42—C43—C38 | −0.2 (3) |
C47—Ru2—P2—C13 | 137.16 (9) | C45—Ru1—C44—O3 | −40.5 (9) |
C49—Ru2—P2—C13 | −38.29 (9) | C46—Ru1—C44—O3 | −149.5 (7) |
Ru3—Ru2—P2—C13 | 54.35 (7) | P1—Ru1—C44—O3 | 54.1 (9) |
Ru1—Ru2—P2—C13 | 42.68 (7) | Ru2—Ru1—C44—O3 | 146.1 (9) |
C7—P1—C1—C2 | 79.20 (18) | Ru3—Ru1—C44—O3 | −159.0 (9) |
C13—P1—C1—C2 | −175.04 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O3i | 0.93 | 2.49 | 3.377 (3) | 159 |
C3—H3A···Cg1ii | 0.93 | 2.93 | 3.708 (3) | 142 |
C22—H22A···Cg2iii | 0.93 | 2.78 | 3.453 (2) | 130 |
C53—H53B···Cg3iv | 0.96 | 2.94 | 3.801 (3) | 150 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Ru3(C21H21As)(C25H22P2)(CO)9] |
Mr | 1287.96 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 11.1241 (1), 12.1660 (2), 20.0895 (3) |
α, β, γ (°) | 91.406 (1), 101.116 (1), 102.473 (1) |
V (Å3) | 2598.63 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.61 |
Crystal size (mm) | 0.29 × 0.22 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.653, 0.907 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 104298, 24677, 19683 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.831 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.084, 1.02 |
No. of reflections | 24677 |
No. of parameters | 634 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 3.41, −1.34 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O3i | 0.9300 | 2.4900 | 3.377 (3) | 159.00 |
C3—H3A···Cg1ii | 0.93 | 2.93 | 3.708 (3) | 142 |
C22—H22A···Cg2iii | 0.93 | 2.78 | 3.453 (2) | 130 |
C53—H53B···Cg3iv | 0.96 | 2.94 | 3.801 (3) | 150 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1, y, z; (iii) x−1, y, z; (iv) −x, −y+1, −z. |
Acknowledgements
The authors would like to thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research grant 1001/PJJAUH/811115. IAK is grateful to USM for a Postdoctoral Fellowship and Gokhale Centenary College, Ankola, Karnataka, India, for study leave. HKF thanks USM for the Research University Golden Goose grant 1001/PFIZIK/811012. CSY thanks USM for the award of a USM Fellowship.
References
Bruce, M. I., Liddell, M. J., Hughes, C. A., Patrick, J. M., Skelton, B. W. & White, A. H. (1988a). J. Organomet. Chem. 347, 181–205. CSD CrossRef CAS Web of Science Google Scholar
Bruce, M. I., Liddell, M. J., Shawkataly, O. bin., Hughes, C. A., Skelton, B. W. & White, A. H. (1988b). J. Organomet. Chem. 347, 207–235. CSD CrossRef CAS Web of Science Google Scholar
Bruce, M. I., Matisons, J. G. & Nicholson, B. K. (1983). J. Organomet. Chem. 247, 321–343. CrossRef CAS Web of Science Google Scholar
Bruce, M. I., Shawkataly, O. bin. & Williams, M. L. (1985). J. Organomet. Chem. 287, 127–131. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Shawkataly, O. bin, Chong, M-L, Fun, H.-K., Didierjean, C. & Aubry, A. (2006). Acta Cryst. E62, m168–m169. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shawkataly, O. bin, Khan, I. A., Yeap, C. S. & Fun, H.-K. (2009a). Acta Cryst. E65, m1620–m1621. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shawkataly, O. bin, Khan, I. A., Yeap, C. S. & Fun, H.-K. (2009b). Acta Cryst. E65, o2772–o2773. Web of Science CrossRef IUCr Journals Google Scholar
Shawkataly, O. bin, Pankhi, M. A. A., Khan, I. A., Yeap, C. S. & Fun, H.-K. (2009c). Acta Cryst. E65, o1525–o1526. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shawkataly, O. bin., Ramalingam, K., Lee, S. T., Parameswary, M., Fun, H.-K. & Sivakumar, K. (1998). Polyhedron, 17, 1211–1216. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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.
Tri-angulotriruthenium clusters are known for their interesting structural variations and related catalytic activity. A large number of substituted derivatives, Ru3(CO)12-nLn (L=15 group ligand) have been reported (Bruce et al., 1988a,b; Bruce et al., 1985). In continuation of our interest in the substituted clusters (Shawkataly et al., 1998, 2009a) we report here the synthesis and structure of Ru3(CO)9(µ-Ph2PCH2PPh2)(As(4-CH3C6H4)3).
The bond lengths and angles of title compound (Fig. 1) are comparable to those in related structures (Shawkataly et al., 2006, 2009a,b,c). The bis(diphenylphosphino)methane ligand bridges the Ru1—Ru2 bond and the monodentate arsine ligand bonds to the Ru3 atom. Both the phosphine and arsine ligands are equatorial with respect to the Ru3 triangle. Additionally, each Ru atom carries one equatorial and two axial terminal carbonyl ligands. The three arsine substituted phenyl rings make dihedral angles (C26–C31/C32–C37, C26–C31/C38–C43 and C32–C37/C38–C43) of 87.36 (10), 81.96 (10) and 73.37 (11)° with each other respectively. The dihedral angles between the two phenyl rings (C1–C6/C7–C12 and C14–C19/C20–C25) are 88.08 (12) and 80.15 (10)° for the two diphenylphosphino groups respectively.
In the crystal packing (Fig. 2), the molecules are linked together as dimers via intermolecular C—H···O hydrogen bonds. These dimers are stacked down b axis. Intermolecular C—H···π (Table 1) and π–π interactions further stabilize the crystal structure with Cg4···Cg4 = 3.6383 (13) Å, -1 - x, -y, 1 - z (Cg4 is centroid of phenyl ring C14–C19).