metal-organic compounds
Undecacarbonyl-1κ3C,2κ4C,3κ4C-[tris(4-methylphenyl)arsine-1κAs]-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)(CO)11], one equatorial carbonyl group has been substituted by the monodentate arsine ligand, leaving one equatorial and two axial carbonyl substituents on the Ru atom. The remaining two Ru atoms each carry two equatorial and two axial terminal carbonyl ligands. The three arsine-substituted phenyl rings make dihedral angles of 73.2 (2), 71.0 (2) and 75.3 (2)° with each other. In the crystal packing, molecules are stacked down the b axis and each molecule is stabilized by an intramolecular C—H⋯O hydrogen bond.
Related literature
For general background to triangulo-triruthenium derivatives, see: Bruce et al. (1985, 1988a,b); Shawkataly et al. (1998, 2004). For related structures, see: Shawkataly et al. (2006, 2009a,b). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
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Refinement
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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/S1600536809046935/sj2671sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809046935/sj2671Isup2.hkl
The reactions were conducted under an atmosphere of high purity nitrogen using standard Schlenk techniques and tetrahydrofuran (THF) was dried over sodium metal. Tris(4-methylphenyl)arsine (Maybridge) is used as received. Ru3(CO)12 (100 mg, 0.16 mmol) and tris(4-methylphenyl)arsine (56 mg, 0.16 mmol) were stirred in THF (25 ml) under nitrogen. About 0.2 ml of diphenylketyl ν(CO) 2173 s, 2045 s, 2030 s, 1988 s, cm-1. 1H NMR (CDCl3) δ 7.29 (6 H, d, J = 7.98 Hz), δ 7.24 (6 H, d, J = 7.86 Hz), δ 2.40 (s, 9 H, 3CH3).
initiator was introduced into the reaction mixture under a current of nitrogen. The reaction mixture turned intense red. After 10 minutes of stirring the solvent was removed under vacuum. The reaction mixture was separated by TLC (acetone:hexane, 10:90); three bands appeared. The major band (red) Rf = 0.78 yielded the title compound which was crystallized from CH2Cl2—CH3OH, yield = 100 mg, 57%, m.p. 137 °C. IR(cyclohexane).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).[Ru3(C21H21As)(CO)11] | Z = 2 |
Mr = 959.62 | F(000) = 932 |
Triclinic, P1 | Dx = 1.909 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5081 (3) Å | Cell parameters from 9957 reflections |
b = 11.2922 (3) Å | θ = 2.5–29.8° |
c = 14.4625 (4) Å | µ = 2.38 mm−1 |
α = 98.326 (1)° | T = 100 K |
β = 94.056 (2)° | Block, brown |
γ = 98.923 (1)° | 0.33 × 0.16 × 0.08 mm |
V = 1669.83 (8) Å3 |
Bruker SMART APEXII CCD area-detector diffractometer | 9594 independent reflections |
Radiation source: fine-focus sealed tube | 7073 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ϕ and ω scans | θmax = 29.9°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −14→14 |
Tmin = 0.511, Tmax = 0.838 | k = −15→15 |
39493 measured reflections | l = −20→20 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0749P)2 + 0.6277P] where P = (Fo2 + 2Fc2)/3 |
9594 reflections | (Δ/σ)max = 0.001 |
427 parameters | Δρmax = 2.32 e Å−3 |
0 restraints | Δρmin = −1.20 e Å−3 |
[Ru3(C21H21As)(CO)11] | γ = 98.923 (1)° |
Mr = 959.62 | V = 1669.83 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.5081 (3) Å | Mo Kα radiation |
b = 11.2922 (3) Å | µ = 2.38 mm−1 |
c = 14.4625 (4) Å | T = 100 K |
α = 98.326 (1)° | 0.33 × 0.16 × 0.08 mm |
β = 94.056 (2)° |
Bruker SMART APEXII CCD area-detector diffractometer | 9594 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 7073 reflections with I > 2σ(I) |
Tmin = 0.511, Tmax = 0.838 | Rint = 0.051 |
39493 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.06 | Δρmax = 2.32 e Å−3 |
9594 reflections | Δρmin = −1.20 e Å−3 |
427 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 | 0.23059 (3) | 0.12873 (3) | 0.66692 (2) | 0.01823 (9) | |
Ru2 | 0.33724 (4) | 0.23746 (3) | 0.51800 (2) | 0.02163 (10) | |
Ru3 | 0.23882 (4) | 0.38423 (3) | 0.66627 (3) | 0.02160 (10) | |
As1 | 0.13525 (4) | 0.08572 (4) | 0.81172 (3) | 0.01913 (11) | |
O1 | 0.4975 (3) | 0.1608 (3) | 0.7762 (2) | 0.0293 (8) | |
O2 | 0.2735 (4) | −0.1180 (3) | 0.5748 (3) | 0.0360 (9) | |
O3 | −0.0494 (3) | 0.0798 (3) | 0.5754 (2) | 0.0306 (8) | |
O4 | 0.6137 (4) | 0.2848 (3) | 0.6172 (3) | 0.0336 (8) | |
O5 | 0.3994 (4) | 0.0132 (4) | 0.3972 (3) | 0.0488 (11) | |
O6 | 0.0618 (4) | 0.1858 (4) | 0.4178 (2) | 0.0370 (9) | |
O7 | 0.4120 (4) | 0.4309 (4) | 0.3970 (3) | 0.0399 (9) | |
O8 | −0.0382 (4) | 0.3463 (4) | 0.5683 (3) | 0.0538 (12) | |
O9 | 0.1278 (4) | 0.4566 (3) | 0.8512 (3) | 0.0351 (8) | |
O10 | 0.5054 (4) | 0.4325 (3) | 0.7784 (3) | 0.0379 (9) | |
O11 | 0.3037 (4) | 0.6226 (4) | 0.5889 (3) | 0.0493 (11) | |
C1 | 0.2562 (4) | 0.1045 (4) | 0.9228 (3) | 0.0223 (9) | |
C2 | 0.3300 (5) | 0.2195 (4) | 0.9560 (3) | 0.0280 (10) | |
H2A | 0.3235 | 0.2836 | 0.9231 | 0.034* | |
C3 | 0.4123 (5) | 0.2374 (5) | 1.0376 (3) | 0.0328 (11) | |
H3A | 0.4591 | 0.3144 | 1.0598 | 0.039* | |
C4 | 0.4267 (5) | 0.1425 (5) | 1.0873 (3) | 0.0327 (11) | |
C5 | 0.3553 (5) | 0.0296 (5) | 1.0535 (4) | 0.0326 (11) | |
H5A | 0.3651 | −0.0350 | 1.0851 | 0.039* | |
C6 | 0.2684 (5) | 0.0097 (4) | 0.9728 (3) | 0.0264 (10) | |
H6A | 0.2190 | −0.0666 | 0.9526 | 0.032* | |
C7 | 0.0462 (4) | −0.0807 (4) | 0.8001 (3) | 0.0210 (9) | |
C8 | −0.0832 (4) | −0.1076 (4) | 0.8174 (3) | 0.0238 (9) | |
H8A | −0.1272 | −0.0453 | 0.8392 | 0.029* | |
C9 | −0.1461 (4) | −0.2265 (4) | 0.8022 (3) | 0.0247 (10) | |
H9A | −0.2324 | −0.2428 | 0.8140 | 0.030* | |
C10 | −0.0839 (5) | −0.3228 (4) | 0.7697 (3) | 0.0257 (10) | |
C11 | 0.0470 (4) | −0.2935 (4) | 0.7533 (3) | 0.0260 (10) | |
H11A | 0.0916 | −0.3555 | 0.7320 | 0.031* | |
C12 | 0.1103 (4) | −0.1751 (4) | 0.7680 (3) | 0.0238 (9) | |
H12A | 0.1967 | −0.1582 | 0.7563 | 0.029* | |
C13 | 0.0045 (4) | 0.1772 (4) | 0.8591 (3) | 0.0220 (9) | |
C14 | −0.0947 (5) | 0.1967 (4) | 0.7974 (3) | 0.0251 (10) | |
H14A | −0.0983 | 0.1659 | 0.7338 | 0.030* | |
C15 | −0.1886 (5) | 0.2618 (4) | 0.8300 (3) | 0.0277 (10) | |
H15A | −0.2551 | 0.2733 | 0.7880 | 0.033* | |
C16 | −0.1850 (5) | 0.3104 (4) | 0.9248 (3) | 0.0269 (10) | |
C17 | −0.0850 (5) | 0.2906 (4) | 0.9860 (3) | 0.0296 (11) | |
H17A | −0.0805 | 0.3222 | 1.0494 | 0.036* | |
C18 | 0.0087 (5) | 0.2241 (4) | 0.9538 (3) | 0.0237 (9) | |
H18A | 0.0743 | 0.2110 | 0.9958 | 0.028* | |
C19 | 0.5165 (5) | 0.1637 (6) | 1.1765 (4) | 0.0462 (15) | |
H19A | 0.5476 | 0.0899 | 1.1846 | 0.069* | |
H19B | 0.4707 | 0.1888 | 1.2290 | 0.069* | |
H19C | 0.5885 | 0.2260 | 1.1726 | 0.069* | |
C20 | −0.1530 (5) | −0.4518 (4) | 0.7531 (4) | 0.0362 (12) | |
H20A | −0.2420 | −0.4534 | 0.7645 | 0.054* | |
H20B | −0.1130 | −0.4971 | 0.7948 | 0.054* | |
H20C | −0.1480 | −0.4873 | 0.6893 | 0.054* | |
C21 | −0.2861 (5) | 0.3826 (5) | 0.9587 (4) | 0.0380 (13) | |
H21A | −0.2986 | 0.3736 | 1.0226 | 0.057* | |
H21B | −0.3661 | 0.3537 | 0.9200 | 0.057* | |
H21C | −0.2581 | 0.4668 | 0.9551 | 0.057* | |
C22 | 0.4009 (5) | 0.1548 (4) | 0.7333 (3) | 0.0240 (10) | |
C23 | 0.2559 (5) | −0.0277 (4) | 0.6123 (3) | 0.0258 (10) | |
C24 | 0.0568 (5) | 0.1036 (4) | 0.6070 (3) | 0.0239 (9) | |
C25 | 0.5090 (5) | 0.2675 (4) | 0.5847 (3) | 0.0272 (10) | |
C26 | 0.3754 (5) | 0.0942 (5) | 0.4432 (4) | 0.0333 (12) | |
C27 | 0.1617 (5) | 0.2062 (4) | 0.4593 (3) | 0.0291 (11) | |
C28 | 0.3839 (5) | 0.3601 (4) | 0.4424 (3) | 0.0284 (10) | |
C29 | 0.0661 (6) | 0.3529 (5) | 0.6015 (4) | 0.0371 (12) | |
C30 | 0.1685 (5) | 0.4274 (4) | 0.7818 (4) | 0.0278 (10) | |
C31 | 0.4087 (5) | 0.4051 (4) | 0.7326 (3) | 0.0279 (10) | |
C32 | 0.2800 (5) | 0.5349 (5) | 0.6172 (4) | 0.0349 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.02275 (18) | 0.01272 (16) | 0.01969 (18) | 0.00001 (13) | 0.00294 (14) | 0.00684 (12) |
Ru2 | 0.0286 (2) | 0.01625 (17) | 0.02074 (18) | 0.00008 (14) | 0.00498 (15) | 0.00777 (13) |
Ru3 | 0.0266 (2) | 0.01339 (17) | 0.0261 (2) | 0.00331 (14) | 0.00339 (15) | 0.00697 (13) |
As1 | 0.0225 (2) | 0.0156 (2) | 0.0200 (2) | 0.00051 (17) | 0.00296 (17) | 0.00779 (16) |
O1 | 0.0243 (18) | 0.0347 (19) | 0.0322 (19) | 0.0051 (15) | 0.0022 (15) | 0.0163 (15) |
O2 | 0.048 (2) | 0.0194 (17) | 0.044 (2) | 0.0094 (16) | 0.0120 (18) | 0.0070 (15) |
O3 | 0.0290 (19) | 0.038 (2) | 0.0229 (18) | 0.0029 (16) | 0.0010 (15) | 0.0033 (15) |
O4 | 0.031 (2) | 0.037 (2) | 0.035 (2) | 0.0020 (16) | 0.0028 (16) | 0.0131 (16) |
O5 | 0.071 (3) | 0.033 (2) | 0.044 (2) | 0.013 (2) | 0.019 (2) | 0.0005 (18) |
O6 | 0.038 (2) | 0.042 (2) | 0.0274 (19) | −0.0079 (18) | −0.0041 (16) | 0.0119 (16) |
O7 | 0.038 (2) | 0.044 (2) | 0.038 (2) | −0.0087 (18) | 0.0036 (17) | 0.0252 (18) |
O8 | 0.040 (2) | 0.044 (3) | 0.072 (3) | 0.018 (2) | −0.016 (2) | −0.010 (2) |
O9 | 0.041 (2) | 0.0279 (18) | 0.038 (2) | 0.0051 (16) | 0.0135 (17) | 0.0072 (15) |
O10 | 0.034 (2) | 0.031 (2) | 0.045 (2) | −0.0017 (17) | −0.0032 (18) | 0.0058 (17) |
O11 | 0.062 (3) | 0.029 (2) | 0.069 (3) | 0.015 (2) | 0.024 (2) | 0.031 (2) |
C1 | 0.023 (2) | 0.025 (2) | 0.020 (2) | 0.0025 (18) | 0.0032 (17) | 0.0098 (17) |
C2 | 0.031 (3) | 0.027 (2) | 0.026 (2) | −0.002 (2) | 0.003 (2) | 0.0085 (19) |
C3 | 0.029 (3) | 0.038 (3) | 0.028 (3) | −0.002 (2) | 0.005 (2) | 0.004 (2) |
C4 | 0.021 (2) | 0.053 (3) | 0.026 (3) | 0.014 (2) | −0.0001 (19) | 0.007 (2) |
C5 | 0.035 (3) | 0.038 (3) | 0.031 (3) | 0.018 (2) | 0.005 (2) | 0.012 (2) |
C6 | 0.028 (2) | 0.028 (2) | 0.026 (2) | 0.007 (2) | 0.0063 (19) | 0.0085 (19) |
C7 | 0.024 (2) | 0.020 (2) | 0.019 (2) | −0.0006 (17) | 0.0005 (17) | 0.0089 (16) |
C8 | 0.027 (2) | 0.021 (2) | 0.026 (2) | 0.0052 (18) | 0.0089 (19) | 0.0075 (18) |
C9 | 0.021 (2) | 0.022 (2) | 0.032 (2) | −0.0026 (18) | 0.0076 (19) | 0.0077 (18) |
C10 | 0.028 (2) | 0.021 (2) | 0.029 (2) | 0.0006 (19) | 0.000 (2) | 0.0118 (18) |
C11 | 0.026 (2) | 0.020 (2) | 0.037 (3) | 0.0076 (19) | 0.005 (2) | 0.0145 (19) |
C12 | 0.021 (2) | 0.021 (2) | 0.034 (3) | 0.0072 (18) | 0.0046 (19) | 0.0133 (19) |
C13 | 0.025 (2) | 0.018 (2) | 0.024 (2) | −0.0009 (17) | 0.0044 (18) | 0.0096 (17) |
C14 | 0.031 (2) | 0.026 (2) | 0.018 (2) | 0.0010 (19) | 0.0014 (19) | 0.0054 (17) |
C15 | 0.023 (2) | 0.030 (3) | 0.030 (3) | 0.0014 (19) | 0.0019 (19) | 0.010 (2) |
C16 | 0.028 (2) | 0.024 (2) | 0.029 (2) | 0.0022 (19) | 0.003 (2) | 0.0078 (19) |
C17 | 0.039 (3) | 0.027 (2) | 0.024 (2) | 0.005 (2) | 0.006 (2) | 0.0048 (19) |
C18 | 0.027 (2) | 0.026 (2) | 0.021 (2) | 0.0073 (19) | −0.0003 (18) | 0.0102 (18) |
C19 | 0.031 (3) | 0.070 (4) | 0.036 (3) | 0.015 (3) | −0.006 (2) | 0.003 (3) |
C20 | 0.035 (3) | 0.021 (2) | 0.054 (3) | 0.000 (2) | 0.008 (2) | 0.012 (2) |
C21 | 0.035 (3) | 0.047 (3) | 0.037 (3) | 0.016 (3) | 0.004 (2) | 0.010 (2) |
C22 | 0.033 (3) | 0.014 (2) | 0.027 (2) | 0.0016 (18) | 0.008 (2) | 0.0114 (17) |
C23 | 0.036 (3) | 0.019 (2) | 0.024 (2) | 0.002 (2) | 0.005 (2) | 0.0096 (18) |
C24 | 0.034 (3) | 0.020 (2) | 0.020 (2) | 0.0051 (19) | 0.0072 (19) | 0.0061 (17) |
C25 | 0.036 (3) | 0.025 (2) | 0.024 (2) | 0.007 (2) | 0.008 (2) | 0.0117 (19) |
C26 | 0.045 (3) | 0.027 (3) | 0.028 (3) | 0.003 (2) | 0.009 (2) | 0.007 (2) |
C27 | 0.039 (3) | 0.025 (2) | 0.024 (2) | 0.000 (2) | 0.007 (2) | 0.0107 (19) |
C28 | 0.030 (3) | 0.025 (2) | 0.029 (2) | −0.002 (2) | 0.000 (2) | 0.0074 (19) |
C29 | 0.043 (3) | 0.023 (3) | 0.044 (3) | 0.013 (2) | −0.003 (3) | −0.002 (2) |
C30 | 0.032 (3) | 0.016 (2) | 0.037 (3) | 0.0036 (19) | 0.002 (2) | 0.0096 (19) |
C31 | 0.041 (3) | 0.016 (2) | 0.028 (2) | 0.002 (2) | 0.007 (2) | 0.0083 (18) |
C32 | 0.040 (3) | 0.029 (3) | 0.039 (3) | 0.008 (2) | 0.012 (2) | 0.010 (2) |
Ru1—C23 | 1.893 (5) | C4—C19 | 1.510 (7) |
Ru1—C24 | 1.927 (5) | C5—C6 | 1.399 (7) |
Ru1—C22 | 1.929 (5) | C5—H5A | 0.9300 |
Ru1—As1 | 2.4629 (5) | C6—H6A | 0.9300 |
Ru1—Ru2 | 2.8430 (5) | C7—C12 | 1.389 (6) |
Ru1—Ru3 | 2.8745 (5) | C7—C8 | 1.395 (6) |
Ru2—C28 | 1.912 (5) | C8—C9 | 1.381 (6) |
Ru2—C26 | 1.925 (5) | C8—H8A | 0.9300 |
Ru2—C27 | 1.933 (6) | C9—C10 | 1.396 (6) |
Ru2—C25 | 1.942 (5) | C9—H9A | 0.9300 |
Ru2—Ru3 | 2.8690 (5) | C10—C11 | 1.409 (6) |
Ru3—C30 | 1.905 (5) | C10—C20 | 1.500 (7) |
Ru3—C31 | 1.929 (6) | C11—C12 | 1.378 (6) |
Ru3—C32 | 1.937 (5) | C11—H11A | 0.9300 |
Ru3—C29 | 1.940 (6) | C12—H12A | 0.9300 |
As1—C1 | 1.942 (5) | C13—C14 | 1.389 (6) |
As1—C7 | 1.943 (4) | C13—C18 | 1.389 (6) |
As1—C13 | 1.948 (4) | C14—C15 | 1.389 (7) |
O1—C22 | 1.139 (6) | C14—H14A | 0.9300 |
O2—C23 | 1.132 (5) | C15—C16 | 1.396 (7) |
O3—C24 | 1.150 (6) | C15—H15A | 0.9300 |
O4—C25 | 1.142 (6) | C16—C17 | 1.392 (7) |
O5—C26 | 1.122 (6) | C16—C21 | 1.503 (7) |
O6—C27 | 1.145 (6) | C17—C18 | 1.394 (6) |
O7—C28 | 1.124 (6) | C17—H17A | 0.9300 |
O8—C29 | 1.151 (7) | C18—H18A | 0.9300 |
O9—C30 | 1.142 (6) | C19—H19A | 0.9600 |
O10—C31 | 1.147 (6) | C19—H19B | 0.9600 |
O11—C32 | 1.124 (6) | C19—H19C | 0.9600 |
C1—C6 | 1.392 (6) | C20—H20A | 0.9600 |
C1—C2 | 1.405 (6) | C20—H20B | 0.9600 |
C2—C3 | 1.384 (7) | C20—H20C | 0.9600 |
C2—H2A | 0.9300 | C21—H21A | 0.9600 |
C3—C4 | 1.395 (8) | C21—H21B | 0.9600 |
C3—H3A | 0.9300 | C21—H21C | 0.9600 |
C4—C5 | 1.378 (8) | ||
C23—Ru1—C24 | 92.0 (2) | C1—C6—H6A | 120.1 |
C23—Ru1—C22 | 89.4 (2) | C5—C6—H6A | 120.1 |
C24—Ru1—C22 | 176.97 (18) | C12—C7—C8 | 119.1 (4) |
C23—Ru1—As1 | 101.53 (13) | C12—C7—As1 | 119.2 (3) |
C24—Ru1—As1 | 87.54 (13) | C8—C7—As1 | 121.6 (3) |
C22—Ru1—As1 | 89.57 (13) | C9—C8—C7 | 120.1 (4) |
C23—Ru1—Ru2 | 92.35 (13) | C9—C8—H8A | 119.9 |
C24—Ru1—Ru2 | 92.87 (13) | C7—C8—H8A | 119.9 |
C22—Ru1—Ru2 | 89.73 (12) | C8—C9—C10 | 121.9 (4) |
As1—Ru1—Ru2 | 166.094 (19) | C8—C9—H9A | 119.0 |
C23—Ru1—Ru3 | 152.51 (13) | C10—C9—H9A | 119.0 |
C24—Ru1—Ru3 | 87.74 (13) | C9—C10—C11 | 116.9 (4) |
C22—Ru1—Ru3 | 92.21 (13) | C9—C10—C20 | 121.6 (4) |
As1—Ru1—Ru3 | 105.919 (17) | C11—C10—C20 | 121.4 (4) |
Ru2—Ru1—Ru3 | 60.235 (12) | C12—C11—C10 | 121.5 (4) |
C28—Ru2—C26 | 102.5 (2) | C12—C11—H11A | 119.2 |
C28—Ru2—C27 | 90.7 (2) | C10—C11—H11A | 119.2 |
C26—Ru2—C27 | 91.0 (2) | C11—C12—C7 | 120.4 (4) |
C28—Ru2—C25 | 92.3 (2) | C11—C12—H12A | 119.8 |
C26—Ru2—C25 | 90.7 (2) | C7—C12—H12A | 119.8 |
C27—Ru2—C25 | 176.23 (18) | C14—C13—C18 | 119.2 (4) |
C28—Ru2—Ru1 | 158.50 (15) | C14—C13—As1 | 119.6 (3) |
C26—Ru2—Ru1 | 98.74 (15) | C18—C13—As1 | 121.2 (3) |
C27—Ru2—Ru1 | 85.47 (13) | C13—C14—C15 | 120.3 (4) |
C25—Ru2—Ru1 | 90.94 (13) | C13—C14—H14A | 119.8 |
C28—Ru2—Ru3 | 98.21 (15) | C15—C14—H14A | 119.8 |
C26—Ru2—Ru3 | 159.03 (15) | C14—C15—C16 | 121.2 (5) |
C27—Ru2—Ru3 | 85.33 (14) | C14—C15—H15A | 119.4 |
C25—Ru2—Ru3 | 91.90 (14) | C16—C15—H15A | 119.4 |
Ru1—Ru2—Ru3 | 60.427 (12) | C17—C16—C15 | 118.0 (4) |
C30—Ru3—C31 | 89.9 (2) | C17—C16—C21 | 121.5 (4) |
C30—Ru3—C32 | 105.2 (2) | C15—C16—C21 | 120.5 (5) |
C31—Ru3—C32 | 92.2 (2) | C16—C17—C18 | 121.1 (4) |
C30—Ru3—C29 | 89.7 (2) | C16—C17—H17A | 119.5 |
C31—Ru3—C29 | 176.4 (2) | C18—C17—H17A | 119.5 |
C32—Ru3—C29 | 91.3 (2) | C13—C18—C17 | 120.3 (4) |
C30—Ru3—Ru2 | 159.15 (14) | C13—C18—H18A | 119.9 |
C31—Ru3—Ru2 | 86.66 (14) | C17—C18—H18A | 119.9 |
C32—Ru3—Ru2 | 95.54 (15) | C4—C19—H19A | 109.5 |
C29—Ru3—Ru2 | 92.39 (16) | C4—C19—H19B | 109.5 |
C30—Ru3—Ru1 | 99.92 (14) | H19A—C19—H19B | 109.5 |
C31—Ru3—Ru1 | 86.07 (14) | C4—C19—H19C | 109.5 |
C32—Ru3—Ru1 | 154.87 (15) | H19A—C19—H19C | 109.5 |
C29—Ru3—Ru1 | 90.44 (16) | H19B—C19—H19C | 109.5 |
Ru2—Ru3—Ru1 | 59.337 (12) | C10—C20—H20A | 109.5 |
C1—As1—C7 | 103.68 (19) | C10—C20—H20B | 109.5 |
C1—As1—C13 | 101.46 (19) | H20A—C20—H20B | 109.5 |
C7—As1—C13 | 101.89 (18) | C10—C20—H20C | 109.5 |
C1—As1—Ru1 | 115.94 (13) | H20A—C20—H20C | 109.5 |
C7—As1—Ru1 | 112.36 (12) | H20B—C20—H20C | 109.5 |
C13—As1—Ru1 | 119.40 (12) | C16—C21—H21A | 109.5 |
C6—C1—C2 | 119.0 (4) | C16—C21—H21B | 109.5 |
C6—C1—As1 | 122.5 (4) | H21A—C21—H21B | 109.5 |
C2—C1—As1 | 118.5 (3) | C16—C21—H21C | 109.5 |
C3—C2—C1 | 119.9 (5) | H21A—C21—H21C | 109.5 |
C3—C2—H2A | 120.0 | H21B—C21—H21C | 109.5 |
C1—C2—H2A | 120.0 | O1—C22—Ru1 | 173.5 (4) |
C2—C3—C4 | 121.5 (5) | O2—C23—Ru1 | 175.6 (4) |
C2—C3—H3A | 119.2 | O3—C24—Ru1 | 173.8 (4) |
C4—C3—H3A | 119.2 | O4—C25—Ru2 | 174.6 (4) |
C5—C4—C3 | 118.1 (5) | O5—C26—Ru2 | 177.4 (5) |
C5—C4—C19 | 121.1 (5) | O6—C27—Ru2 | 174.5 (4) |
C3—C4—C19 | 120.8 (5) | O7—C28—Ru2 | 179.0 (5) |
C4—C5—C6 | 121.6 (5) | O8—C29—Ru3 | 172.5 (5) |
C4—C5—H5A | 119.2 | O9—C30—Ru3 | 178.1 (4) |
C6—C5—H5A | 119.2 | O10—C31—Ru3 | 170.3 (4) |
C1—C6—C5 | 119.8 (5) | O11—C32—Ru3 | 179.8 (5) |
C23—Ru1—Ru2—C28 | 170.9 (4) | C23—Ru1—Ru3—Ru2 | −4.6 (3) |
C24—Ru1—Ru2—C28 | 78.8 (4) | C24—Ru1—Ru3—Ru2 | −94.61 (12) |
C22—Ru1—Ru2—C28 | −99.7 (4) | C22—Ru1—Ru3—Ru2 | 88.42 (13) |
As1—Ru1—Ru2—C28 | −12.6 (4) | As1—Ru1—Ru3—Ru2 | 178.60 (2) |
Ru3—Ru1—Ru2—C28 | −7.0 (4) | C23—Ru1—As1—C1 | 93.0 (2) |
C23—Ru1—Ru2—C26 | 0.4 (2) | C24—Ru1—As1—C1 | −175.5 (2) |
C24—Ru1—Ru2—C26 | −91.7 (2) | C22—Ru1—As1—C1 | 3.6 (2) |
C22—Ru1—Ru2—C26 | 89.8 (2) | Ru2—Ru1—As1—C1 | −83.48 (17) |
As1—Ru1—Ru2—C26 | 176.92 (19) | Ru3—Ru1—As1—C1 | −88.53 (15) |
Ru3—Ru1—Ru2—C26 | −177.48 (17) | C23—Ru1—As1—C7 | −26.0 (2) |
C23—Ru1—Ru2—C27 | 90.7 (2) | C24—Ru1—As1—C7 | 65.6 (2) |
C24—Ru1—Ru2—C27 | −1.45 (19) | C22—Ru1—As1—C7 | −115.3 (2) |
C22—Ru1—Ru2—C27 | −179.89 (19) | Ru2—Ru1—As1—C7 | 157.54 (16) |
As1—Ru1—Ru2—C27 | −92.79 (17) | Ru3—Ru1—As1—C7 | 152.49 (15) |
Ru3—Ru1—Ru2—C27 | −87.19 (15) | C23—Ru1—As1—C13 | −145.2 (2) |
C23—Ru1—Ru2—C25 | −90.5 (2) | C24—Ru1—As1—C13 | −53.6 (2) |
C24—Ru1—Ru2—C25 | 177.40 (19) | C22—Ru1—As1—C13 | 125.5 (2) |
C22—Ru1—Ru2—C25 | −1.05 (19) | Ru2—Ru1—As1—C13 | 38.38 (18) |
As1—Ru1—Ru2—C25 | 86.05 (16) | Ru3—Ru1—As1—C13 | 33.32 (16) |
Ru3—Ru1—Ru2—C25 | 91.65 (14) | C7—As1—C1—C6 | 2.4 (4) |
C23—Ru1—Ru2—Ru3 | 177.87 (15) | C13—As1—C1—C6 | 107.8 (4) |
C24—Ru1—Ru2—Ru3 | 85.74 (13) | Ru1—As1—C1—C6 | −121.3 (3) |
C22—Ru1—Ru2—Ru3 | −92.71 (13) | C7—As1—C1—C2 | −174.9 (3) |
As1—Ru1—Ru2—Ru3 | −5.60 (8) | C13—As1—C1—C2 | −69.5 (4) |
C28—Ru2—Ru3—C30 | −176.1 (5) | Ru1—As1—C1—C2 | 61.5 (4) |
C26—Ru2—Ru3—C30 | 13.4 (6) | C6—C1—C2—C3 | −0.6 (7) |
C27—Ru2—Ru3—C30 | 93.9 (5) | As1—C1—C2—C3 | 176.8 (4) |
C25—Ru2—Ru3—C30 | −83.6 (5) | C1—C2—C3—C4 | 1.6 (7) |
Ru1—Ru2—Ru3—C30 | 6.4 (4) | C2—C3—C4—C5 | −0.7 (7) |
C28—Ru2—Ru3—C31 | −95.2 (2) | C2—C3—C4—C19 | −179.7 (5) |
C26—Ru2—Ru3—C31 | 94.4 (5) | C3—C4—C5—C6 | −1.3 (7) |
C27—Ru2—Ru3—C31 | 174.85 (19) | C19—C4—C5—C6 | 177.7 (5) |
C25—Ru2—Ru3—C31 | −2.59 (18) | C2—C1—C6—C5 | −1.3 (6) |
Ru1—Ru2—Ru3—C31 | 87.41 (13) | As1—C1—C6—C5 | −178.6 (3) |
C28—Ru2—Ru3—C32 | −3.2 (2) | C4—C5—C6—C1 | 2.3 (7) |
C26—Ru2—Ru3—C32 | −173.7 (5) | C1—As1—C7—C12 | −74.5 (4) |
C27—Ru2—Ru3—C32 | −93.2 (2) | C13—As1—C7—C12 | −179.6 (4) |
C25—Ru2—Ru3—C32 | 89.3 (2) | Ru1—As1—C7—C12 | 51.4 (4) |
Ru1—Ru2—Ru3—C32 | 179.35 (18) | C1—As1—C7—C8 | 109.7 (4) |
C28—Ru2—Ru3—C29 | 88.3 (2) | C13—As1—C7—C8 | 4.6 (4) |
C26—Ru2—Ru3—C29 | −82.1 (5) | Ru1—As1—C7—C8 | −124.4 (3) |
C27—Ru2—Ru3—C29 | −1.7 (2) | C12—C7—C8—C9 | −0.3 (7) |
C25—Ru2—Ru3—C29 | −179.1 (2) | As1—C7—C8—C9 | 175.5 (3) |
Ru1—Ru2—Ru3—C29 | −89.09 (17) | C7—C8—C9—C10 | 0.1 (7) |
C28—Ru2—Ru3—Ru1 | 177.43 (15) | C8—C9—C10—C11 | 0.2 (7) |
C26—Ru2—Ru3—Ru1 | 7.0 (5) | C8—C9—C10—C20 | −179.8 (5) |
C27—Ru2—Ru3—Ru1 | 87.44 (13) | C9—C10—C11—C12 | −0.4 (7) |
C25—Ru2—Ru3—Ru1 | −90.00 (13) | C20—C10—C11—C12 | 179.6 (5) |
C23—Ru1—Ru3—C30 | 177.7 (4) | C10—C11—C12—C7 | 0.3 (7) |
C24—Ru1—Ru3—C30 | 87.7 (2) | C8—C7—C12—C11 | 0.1 (7) |
C22—Ru1—Ru3—C30 | −89.3 (2) | As1—C7—C12—C11 | −175.8 (4) |
As1—Ru1—Ru3—C30 | 0.93 (16) | C1—As1—C13—C14 | 173.4 (4) |
Ru2—Ru1—Ru3—C30 | −177.67 (16) | C7—As1—C13—C14 | −79.8 (4) |
C23—Ru1—Ru3—C31 | −93.0 (4) | Ru1—As1—C13—C14 | 44.6 (4) |
C24—Ru1—Ru3—C31 | 176.95 (18) | C1—As1—C13—C18 | −6.3 (4) |
C22—Ru1—Ru3—C31 | −0.02 (18) | C7—As1—C13—C18 | 100.5 (4) |
As1—Ru1—Ru3—C31 | 90.16 (14) | Ru1—As1—C13—C18 | −135.1 (3) |
Ru2—Ru1—Ru3—C31 | −88.44 (14) | C18—C13—C14—C15 | −0.2 (7) |
C23—Ru1—Ru3—C32 | −6.1 (5) | As1—C13—C14—C15 | −179.9 (3) |
C24—Ru1—Ru3—C32 | −96.1 (4) | C13—C14—C15—C16 | 0.8 (7) |
C22—Ru1—Ru3—C32 | 86.9 (4) | C14—C15—C16—C17 | −0.6 (7) |
As1—Ru1—Ru3—C32 | 177.1 (4) | C14—C15—C16—C21 | 178.9 (5) |
Ru2—Ru1—Ru3—C32 | −1.5 (4) | C15—C16—C17—C18 | −0.1 (7) |
C23—Ru1—Ru3—C29 | 87.9 (4) | C21—C16—C17—C18 | −179.6 (5) |
C24—Ru1—Ru3—C29 | −2.1 (2) | C14—C13—C18—C17 | −0.5 (7) |
C22—Ru1—Ru3—C29 | −179.1 (2) | As1—C13—C18—C17 | 179.2 (3) |
As1—Ru1—Ru3—C29 | −88.88 (17) | C16—C17—C18—C13 | 0.7 (7) |
Ru2—Ru1—Ru3—C29 | 92.52 (17) |
Experimental details
Crystal data | |
Chemical formula | [Ru3(C21H21As)(CO)11] |
Mr | 959.62 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 10.5081 (3), 11.2922 (3), 14.4625 (4) |
α, β, γ (°) | 98.326 (1), 94.056 (2), 98.923 (1) |
V (Å3) | 1669.83 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.38 |
Crystal size (mm) | 0.33 × 0.16 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.511, 0.838 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 39493, 9594, 7073 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.702 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.133, 1.06 |
No. of reflections | 9594 |
No. of parameters | 427 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.32, −1.20 |
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 |
C14—H14A···O3 | 0.9300 | 2.4800 | 3.385 (5) | 165.00 |
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 to 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
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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.
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, Ramalingam et al., 1998, 2004; Shawkataly et al., 2005, 2009a) we report here the synthesis and structure of Ru3(CO)11(As(4-CH3C6H4)3).
The bond lengths and angles of title compound (Fig. 1) are comparable to those found in related structures (Shawkataly et al., 2006, 2009a,b). The tri-angulotriruthenium is bonded to a monodentate arsine ligand. The arsine ligand is equatorial with respect to the Ru3 triangle. Additionally, the Ru2 and Ru3 atoms each carry two equatorial and two axial terminal carbonyl ligands except for arsine-bonded Ru1 atom which binds one equatorial and two axial terminal carbonyl ligands. The three arsine-substituted benzene rings make dihedral angles of 73.2 (2), 71.0 (2) and 75.3 (2)° with each other.
In the crystal packing, the molecules are stacked down b axis (Fig. 2) and each molecule is stabilized by an intramolecular C14—H14A···O3 hydrogen bond (Table 1).