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Acta Cryst. (2009). E65, m1620-m1621    [ doi:10.1107/S1600536809047229 ]

[[mu]-Bis(diphenylarsino)methane-1:2[kappa]2As:As']nonacarbonyl-1[kappa]3C,2[kappa]3C,3[kappa]3C-[tris(4-fluorophenyl)phosphine-3[kappa]P]-triangulo-triruthenium(0)

O. bin Shawkataly, I. A. Khan, C. S. Yeap and H.-K. Fun

Abstract top

In the title triangulo-triruthenium compound, [Ru3(C25H22(As2)(C18H12F3P)(CO)9], the bis(diphenylarsino)methane ligand bridges an Ru-Ru bond and the monodentate phosphine 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 phosphine-substituted rings make dihedral angles of 87.76 (13), 57.43 (13) and 73.81 (12)° with each other. The dihedral angles between the pairs of rings are 69.78 (14) and 83.38 (16)° for the two diphenylarsino groups. In the crystal packing, molecules are linked by intermolecular C-H...F and C-H...O hydrogen bonds, forming two-dimensional planes parallel to the ab plane. These planes are also linked by intermolecular C-H...O hydrogen bonds into a three-dimensional framework. Intermolecular C-H...[pi] interactions further stabilize the crystal structure.

Comment top

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; 1985). In continuation of our interest in the substituted clusters (Shawkataly et al., 1998) we report the synthesis and structure of Ru3(CO)9(µ-Ph2AsCH2AsPh2)(P(4-FC6H4)3). The Cambridge Structural Database (Allen, 2002) revealed no structure of the above cluster.

The bond lengths and angles of title compound (Fig. 1) are comparable to its related structures (Shawkataly et al., 2006; Shawkataly et al., 2009a,b). The bis(diphenylarsino)methane ligand bridges the Ru1—Ru2 bond and the monodentate phosphine 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 phosphine substituted phenyl rings (C26–C31, C32–C37 and C38–C43) make dihedral angles (C26–C31/C32–C37, C26–C31/C38–C43 and C32–C37/C38–C43) of 87.76 (13), 57.43 (13) and 73.81 (12)° with each other respectively. The dihedral angles between the two phenyl rings (C1–C6/C7–C12 and C14–C19/C20–C25) are 69.78 (14) and 83.38 (16)° for the two diphenylarsino groups respectively.

In the crystal packing (Fig. 2), the molecules are linked by intermolecular C23—H23A···F3 and C34—H34A···O3 hydrogen bonds to form two-dimensional planes parallel to ab plane. These planes are further linked by intermolecular C42—H42A···O2 hydrogen bonds into a three-dimensional framework. Intermolecular C—H···π interactions further stabilize the crystal structure (Table 1).

Related literature top

For general background to triangulo-triruthenium derivatives, see: Bruce (1985, 1988a,b); Shawkataly et al. (1998). For related structures, see: Shawkataly et al. (2006, 2009a,b). For the synthesis of bis(diphenylarsino)methane, see: Bruce et al. (1983). For details of the Cambridge Structural Database, see: Allen (2002). Cg1 and Cg2 are the centroids of the C38–C43 and C1–C6 phenyl rings, respectively.

Experimental top

Tris(4-flurophenyl)phosphine (Strem chemicals) is used as received and bis(diphenylarsino)methane (Bruce et al., 1983) was prepared by reported procedure. Ru3(CO)10(µ-Ph2AsCH2AsPh2) (105.5 mg, 0.1 mmol) and tris(4-flurophenyl)phosphine (31.62 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 = 58 mg, 42.29%, m.p. 190 °C. IR(cyclohexane).ν(CO) 2054 s, 1993 s, 1976 s cm-1. 1H NMR (CDCl3), δ 7.32–7.50 (m, 26H, Ph), δ 7.08–7.13 (t, 6H, Ph), δ 4.01 (s, 2H, –CH2–).

Refinement top

All hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å and Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with 20% probability ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the b axis, showing the molecules packed into 3-D framework. Hydrogen atoms not involved in the hydrogen-bonding (dashed lines) have been omitted for clarity.
[µ-Bis(diphenylarsino)methane-1:2κ2As:As']nonacarbonyl- 1κ3C,2κ3C,3κ3C-[tris(4-fluorophenyl)phosphine- 3κP]-triangulo-triruthenium(0) top
Crystal data top
[Ru3(C25H22As2)(C18H12F3P)(CO)9]F(000) = 2632
Mr = 1343.81Dx = 1.748 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9910 reflections
a = 16.3071 (2) Åθ = 2.5–31.1°
b = 16.8142 (2) ŵ = 2.26 mm−1
c = 18.8085 (2) ÅT = 296 K
β = 98.105 (1)°Plate, red
V = 5105.6 (1) Å30.38 × 0.25 × 0.14 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		20637 independent reflections
Radiation source: fine-focus sealed tube13049 reflections with I > 2σ(I)
graphiteRint = 0.032
φ and ω scansθmax = 34.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −25→25
Tmin = 0.478, Tmax = 0.740k = −23→26
89126 measured reflectionsl = −29→22
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0231P)2 + 1.7596P]
where P = (Fo2 + 2Fc2)/3
20637 reflections(Δ/σ)max = 0.002
631 parametersΔρmax = 0.44 e Å−3
0 restraintsΔρmin = −0.54 e Å−3
Crystal data top
[Ru3(C25H22As2)(C18H12F3P)(CO)9]V = 5105.6 (1) Å3
Mr = 1343.81Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.3071 (2) ŵ = 2.26 mm−1
b = 16.8142 (2) ÅT = 296 K
c = 18.8085 (2) Å0.38 × 0.25 × 0.14 mm
β = 98.105 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		20637 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		13049 reflections with I > 2σ(I)
Tmin = 0.478, Tmax = 0.740Rint = 0.032
89126 measured reflectionsθmax = 34.0°
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.067Δρmax = 0.44 e Å−3
S = 1.00Δρmin = −0.54 e Å−3
20637 reflectionsAbsolute structure: ?
631 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ru10.758329 (9)−0.076419 (9)0.204485 (9)0.03449 (4)
Ru20.901268 (9)0.000219 (9)0.278744 (9)0.03474 (4)
Ru30.749043 (9)0.084526 (9)0.254257 (9)0.03606 (4)
As10.822101 (12)−0.206958 (11)0.223901 (11)0.03432 (5)
As20.996032 (11)−0.110301 (12)0.269926 (12)0.03624 (5)
P10.61915 (3)0.14500 (3)0.23231 (3)0.03820 (12)
F10.47921 (13)0.24586 (13)0.49280 (9)0.1049 (7)
F20.58974 (12)0.44950 (10)0.07022 (12)0.1059 (7)
F30.38045 (10)−0.06529 (11)0.05565 (11)0.0960 (6)
O10.84836 (12)−0.05511 (11)0.07344 (10)0.0695 (5)
O20.60490 (12)−0.12226 (13)0.10357 (11)0.0806 (6)
O30.66519 (12)−0.10095 (12)0.33318 (11)0.0714 (5)
O40.85047 (11)−0.08172 (11)0.41116 (10)0.0681 (5)
O51.00783 (13)0.11974 (12)0.36958 (12)0.0836 (6)
O60.95116 (12)0.08300 (11)0.14619 (11)0.0703 (5)
O70.74552 (12)0.09629 (11)0.09135 (10)0.0662 (5)
O80.85238 (12)0.22948 (10)0.29874 (11)0.0750 (6)
O90.71744 (12)0.05435 (11)0.40925 (10)0.0693 (5)
C10.79099 (13)−0.28842 (12)0.15128 (12)0.0415 (5)
C20.79025 (18)−0.36784 (14)0.16849 (15)0.0647 (7)
H2A0.8061−0.38390.21570.078*
C30.7660 (2)−0.42404 (16)0.11581 (18)0.0807 (9)
H3A0.7646−0.47760.12800.097*
C40.74428 (19)−0.40124 (17)0.04610 (17)0.0736 (8)
H4A0.7286−0.43920.01080.088*
C50.7455 (2)−0.32306 (17)0.02835 (15)0.0733 (8)
H5A0.7308−0.3074−0.01920.088*
C60.76868 (17)−0.26642 (15)0.08092 (13)0.0589 (6)
H6A0.7691−0.21290.06840.071*
C70.80087 (12)−0.26512 (12)0.30795 (11)0.0397 (4)
C80.86048 (15)−0.29136 (15)0.36136 (13)0.0580 (6)
H8A0.9156−0.27750.36080.070*
C90.8391 (2)−0.33831 (19)0.41617 (15)0.0769 (8)
H9A0.8799−0.35600.45220.092*
C100.7580 (2)−0.35891 (17)0.41770 (15)0.0720 (8)
H10A0.7441−0.39150.45410.086*
C110.69801 (18)−0.33164 (18)0.36595 (17)0.0733 (8)
H11A0.6429−0.34460.36750.088*
C120.71888 (15)−0.28477 (16)0.31108 (15)0.0626 (7)
H12A0.6776−0.26620.27580.075*
C130.94271 (12)−0.20738 (12)0.22724 (12)0.0398 (4)
H13A0.9559−0.21330.17880.048*
H13B0.9653−0.25300.25490.048*
C141.05731 (12)−0.14627 (13)0.36072 (12)0.0435 (5)
C151.06977 (17)−0.09360 (17)0.41720 (16)0.0715 (8)
H15A1.0507−0.04160.41080.086*
C161.1103 (2)−0.1172 (2)0.48308 (17)0.0928 (11)
H16A1.1191−0.08080.52060.111*
C171.13761 (19)−0.1938 (2)0.49360 (16)0.0802 (9)
H17A1.1637−0.21000.53850.096*
C181.12629 (17)−0.24650 (17)0.43766 (15)0.0682 (7)
H18A1.1451−0.29850.44440.082*
C191.08719 (14)−0.22290 (14)0.37142 (13)0.0516 (6)
H19A1.0808−0.25880.33350.062*
C201.08183 (13)−0.09446 (13)0.20931 (15)0.0499 (6)
C211.16319 (16)−0.08505 (17)0.2382 (2)0.0799 (9)
H21A1.1784−0.08720.28770.096*
C221.2224 (2)−0.0724 (3)0.1941 (3)0.1253 (17)
H22A1.2776−0.06640.21400.150*
C231.2010 (3)−0.0686 (3)0.1217 (3)0.130 (2)
H23A1.2417−0.05990.09250.157*
C241.1203 (3)−0.0775 (2)0.0913 (2)0.1048 (13)
H24A1.1057−0.07520.04170.126*
C251.06032 (19)−0.09009 (18)0.13602 (18)0.0756 (9)
H25A1.0051−0.09560.11610.091*
C260.57217 (14)0.17311 (13)0.31183 (12)0.0466 (5)
C270.49231 (16)0.15401 (17)0.32221 (14)0.0632 (7)
H27A0.45910.12460.28750.076*
C280.46076 (19)0.1780 (2)0.38355 (16)0.0776 (9)
H28A0.40730.16420.39070.093*
C290.5098 (2)0.22193 (18)0.43266 (14)0.0721 (8)
C300.5882 (2)0.24341 (17)0.42481 (15)0.0709 (8)
H30A0.62000.27400.45960.085*
C310.61979 (17)0.21875 (15)0.36371 (14)0.0597 (6)
H31A0.67340.23290.35740.072*
C320.61221 (12)0.24017 (12)0.18371 (12)0.0426 (5)
C330.53927 (15)0.28460 (14)0.17773 (14)0.0552 (6)
H33A0.49510.26640.19950.066*
C340.53190 (17)0.35528 (15)0.13977 (15)0.0649 (7)
H34A0.48340.38500.13610.078*
C350.59754 (18)0.38056 (15)0.10780 (16)0.0664 (7)
C360.66977 (16)0.33947 (15)0.11234 (15)0.0636 (7)
H36A0.71350.35830.09030.076*
C370.67676 (14)0.26870 (14)0.15073 (13)0.0526 (6)
H37A0.72590.23990.15430.063*
C380.54110 (12)0.08408 (13)0.17909 (12)0.0406 (5)
C390.51251 (14)0.01470 (15)0.20801 (14)0.0541 (6)
H39A0.53070.00190.25570.065*
C400.45758 (15)−0.03552 (16)0.16702 (17)0.0644 (7)
H40A0.4379−0.08130.18660.077*
C410.43315 (14)−0.01542 (17)0.09671 (16)0.0621 (7)
C420.46057 (15)0.05001 (17)0.06592 (14)0.0579 (6)
H42A0.44320.06100.01770.069*
C430.51485 (13)0.10050 (14)0.10721 (12)0.0472 (5)
H43A0.53390.14590.08660.057*
C440.81765 (14)−0.05964 (13)0.12443 (13)0.0472 (5)
C450.66118 (14)−0.10384 (14)0.14291 (13)0.0491 (5)
C460.70225 (14)−0.08582 (14)0.28761 (14)0.0497 (5)
C470.86518 (12)−0.05113 (13)0.36024 (13)0.0444 (5)
C480.96867 (14)0.07385 (14)0.33563 (14)0.0523 (6)
C490.92893 (13)0.05136 (13)0.19364 (14)0.0479 (5)
C500.75062 (14)0.08463 (13)0.15216 (14)0.0479 (5)
C510.81181 (14)0.17562 (13)0.28089 (13)0.0471 (5)
C520.73155 (14)0.06203 (13)0.35212 (14)0.0476 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.03469 (7)0.02893 (8)0.03910 (9)−0.00302 (6)0.00266 (6)−0.00330 (7)
Ru20.03017 (7)0.02739 (8)0.04667 (10)−0.00148 (5)0.00549 (6)−0.00464 (7)
Ru30.03345 (7)0.02839 (8)0.04538 (10)0.00152 (6)0.00223 (7)−0.00243 (7)
As10.03681 (9)0.02778 (10)0.03869 (11)−0.00436 (7)0.00647 (8)−0.00183 (8)
As20.03112 (9)0.02945 (10)0.04899 (13)−0.00058 (7)0.00856 (9)−0.00339 (9)
P10.0356 (2)0.0364 (3)0.0421 (3)0.0036 (2)0.0036 (2)−0.0004 (2)
F10.1420 (17)0.1256 (16)0.0524 (10)0.0436 (14)0.0324 (11)−0.0097 (10)
F20.1104 (14)0.0618 (11)0.1438 (18)0.0148 (10)0.0117 (13)0.0494 (11)
F30.0637 (10)0.1025 (14)0.1172 (15)−0.0194 (9)−0.0035 (10)−0.0525 (12)
O10.0940 (14)0.0663 (12)0.0538 (11)−0.0166 (10)0.0300 (10)−0.0113 (9)
O20.0611 (11)0.0898 (15)0.0816 (14)−0.0028 (10)−0.0220 (10)−0.0238 (12)
O30.0743 (12)0.0746 (13)0.0734 (13)−0.0144 (10)0.0382 (11)−0.0073 (10)
O40.0722 (12)0.0739 (13)0.0611 (12)0.0065 (9)0.0192 (10)0.0154 (10)
O50.0797 (13)0.0609 (12)0.1027 (16)−0.0200 (10)−0.0135 (12)−0.0250 (11)
O60.0775 (12)0.0568 (11)0.0818 (14)−0.0046 (9)0.0287 (11)0.0182 (10)
O70.0889 (13)0.0570 (11)0.0523 (11)0.0062 (9)0.0091 (10)0.0036 (9)
O80.0824 (13)0.0430 (10)0.0953 (15)−0.0199 (9)−0.0021 (11)−0.0059 (10)
O90.0901 (14)0.0657 (12)0.0529 (11)0.0191 (10)0.0123 (10)0.0093 (9)
C10.0460 (11)0.0319 (11)0.0477 (13)−0.0054 (8)0.0105 (9)−0.0093 (9)
C20.095 (2)0.0357 (13)0.0606 (16)−0.0064 (12)−0.0008 (14)−0.0063 (12)
C30.120 (3)0.0358 (15)0.085 (2)−0.0107 (15)0.008 (2)−0.0127 (14)
C40.096 (2)0.0546 (17)0.073 (2)−0.0207 (15)0.0233 (17)−0.0319 (15)
C50.115 (2)0.0596 (18)0.0469 (15)−0.0188 (16)0.0186 (16)−0.0166 (13)
C60.0906 (18)0.0412 (13)0.0475 (14)−0.0137 (12)0.0185 (13)−0.0087 (11)
C70.0465 (11)0.0316 (10)0.0421 (12)−0.0043 (8)0.0104 (9)0.0004 (9)
C80.0531 (13)0.0669 (17)0.0532 (15)−0.0070 (12)0.0051 (12)0.0111 (13)
C90.084 (2)0.089 (2)0.0557 (17)0.0009 (17)0.0038 (15)0.0246 (16)
C100.098 (2)0.0651 (19)0.0574 (17)−0.0151 (16)0.0267 (16)0.0148 (14)
C110.0660 (16)0.076 (2)0.081 (2)−0.0195 (14)0.0237 (15)0.0220 (17)
C120.0501 (13)0.0680 (17)0.0704 (17)−0.0111 (12)0.0108 (12)0.0202 (14)
C130.0379 (9)0.0331 (11)0.0496 (12)−0.0014 (8)0.0105 (9)−0.0053 (9)
C140.0369 (10)0.0432 (12)0.0496 (13)0.0025 (8)0.0032 (9)−0.0054 (10)
C150.0713 (17)0.0582 (17)0.076 (2)0.0199 (13)−0.0196 (15)−0.0224 (14)
C160.096 (2)0.097 (2)0.073 (2)0.0368 (19)−0.0300 (18)−0.0384 (19)
C170.083 (2)0.095 (2)0.0556 (17)0.0251 (17)−0.0122 (15)−0.0056 (17)
C180.0735 (17)0.0595 (17)0.0684 (19)0.0149 (13)−0.0006 (14)0.0081 (14)
C190.0577 (13)0.0448 (13)0.0512 (14)0.0078 (10)0.0036 (11)−0.0050 (11)
C200.0449 (11)0.0327 (11)0.0769 (18)0.0009 (9)0.0252 (12)0.0005 (11)
C210.0491 (14)0.077 (2)0.118 (3)−0.0181 (13)0.0283 (16)−0.0133 (18)
C220.065 (2)0.124 (4)0.200 (5)−0.026 (2)0.065 (3)−0.012 (4)
C230.108 (3)0.101 (3)0.209 (6)−0.006 (2)0.115 (4)0.019 (4)
C240.123 (3)0.096 (3)0.113 (3)0.016 (2)0.080 (3)0.024 (2)
C250.0691 (17)0.082 (2)0.084 (2)0.0072 (15)0.0394 (16)0.0145 (17)
C260.0513 (12)0.0468 (13)0.0409 (12)0.0136 (10)0.0040 (10)0.0005 (10)
C270.0565 (14)0.085 (2)0.0494 (15)0.0059 (13)0.0112 (12)−0.0099 (14)
C280.0731 (18)0.103 (2)0.0617 (18)0.0115 (17)0.0265 (15)−0.0069 (17)
C290.097 (2)0.079 (2)0.0426 (15)0.0362 (17)0.0181 (15)0.0000 (14)
C300.093 (2)0.0637 (18)0.0516 (16)0.0205 (16)−0.0037 (15)−0.0136 (13)
C310.0664 (15)0.0543 (15)0.0569 (16)0.0101 (12)0.0030 (13)−0.0108 (12)
C320.0415 (10)0.0367 (11)0.0485 (13)0.0046 (8)0.0028 (9)−0.0018 (9)
C330.0530 (13)0.0498 (14)0.0636 (16)0.0129 (10)0.0104 (12)0.0042 (12)
C340.0661 (16)0.0476 (15)0.0799 (19)0.0211 (12)0.0066 (14)0.0075 (13)
C350.0801 (18)0.0388 (14)0.0773 (19)0.0054 (12)0.0007 (15)0.0135 (13)
C360.0589 (14)0.0495 (15)0.082 (2)−0.0036 (12)0.0088 (14)0.0159 (14)
C370.0479 (12)0.0418 (13)0.0668 (16)0.0022 (10)0.0035 (11)0.0058 (11)
C380.0324 (9)0.0442 (12)0.0457 (12)0.0041 (8)0.0067 (8)−0.0028 (10)
C390.0470 (12)0.0560 (15)0.0589 (15)−0.0035 (10)0.0054 (11)0.0036 (12)
C400.0485 (13)0.0524 (15)0.094 (2)−0.0106 (11)0.0154 (14)−0.0067 (15)
C410.0369 (11)0.0715 (18)0.0768 (19)−0.0007 (11)0.0044 (12)−0.0318 (15)
C420.0509 (13)0.0739 (18)0.0474 (14)0.0114 (12)0.0018 (11)−0.0185 (13)
C430.0460 (11)0.0516 (14)0.0446 (13)0.0057 (10)0.0090 (10)−0.0065 (10)
C440.0578 (13)0.0340 (12)0.0498 (14)−0.0071 (9)0.0075 (11)−0.0050 (10)
C450.0475 (12)0.0447 (13)0.0523 (14)−0.0011 (10)−0.0024 (11)−0.0052 (11)
C460.0439 (11)0.0491 (14)0.0567 (15)−0.0063 (10)0.0090 (11)−0.0108 (11)
C470.0388 (10)0.0403 (12)0.0544 (14)0.0031 (8)0.0076 (10)−0.0033 (11)
C480.0455 (12)0.0411 (13)0.0684 (16)−0.0056 (9)0.0015 (11)−0.0060 (11)
C490.0447 (11)0.0347 (12)0.0652 (16)−0.0002 (9)0.0104 (11)−0.0002 (11)
C500.0488 (12)0.0423 (13)0.0521 (14)0.0028 (9)0.0057 (11)−0.0063 (11)
C510.0497 (12)0.0349 (12)0.0554 (14)−0.0004 (9)0.0029 (10)−0.0004 (10)
C520.0491 (12)0.0371 (12)0.0548 (15)0.0075 (9)0.0013 (11)0.0018 (10)
Geometric parameters (Å, °) top
Ru1—C451.883 (2)C11—H11A0.9300
Ru1—C441.922 (2)C12—H12A0.9300
Ru1—C461.926 (3)C13—H13A0.9700
Ru1—As12.4342 (3)C13—H13B0.9700
Ru1—Ru22.8507 (2)C14—C151.376 (3)
Ru1—Ru32.8745 (2)C14—C191.382 (3)
Ru2—C481.885 (2)C15—C161.378 (4)
Ru2—C471.922 (2)C15—H15A0.9300
Ru2—C491.926 (3)C16—C171.369 (4)
Ru2—As22.4374 (2)C16—H16A0.9300
Ru2—Ru32.8392 (2)C17—C181.368 (4)
Ru3—C511.871 (2)C17—H17A0.9300
Ru3—C501.924 (3)C18—C191.376 (3)
Ru3—C521.939 (3)C18—H18A0.9300
Ru3—P12.3334 (5)C19—H19A0.9300
As1—C71.931 (2)C20—C211.370 (3)
As1—C11.950 (2)C20—C251.376 (4)
As1—C131.9589 (19)C21—C221.376 (5)
As2—C201.944 (2)C21—H21A0.9300
As2—C141.949 (2)C22—C231.359 (7)
As2—C131.9668 (19)C22—H22A0.9300
P1—C381.820 (2)C23—C241.367 (6)
P1—C261.836 (2)C23—H23A0.9300
P1—C321.838 (2)C24—C251.393 (4)
F1—C291.360 (3)C24—H24A0.9300
F2—C351.354 (3)C25—H25A0.9300
F3—C411.360 (3)C26—C271.382 (3)
O1—C441.145 (3)C26—C311.389 (3)
O2—C451.138 (3)C27—C281.388 (4)
O3—C461.145 (3)C27—H27A0.9300
O4—C471.142 (3)C28—C291.353 (4)
O5—C481.138 (3)C28—H28A0.9300
O6—C491.141 (3)C29—C301.356 (4)
O7—C501.152 (3)C30—C311.388 (4)
O8—C511.144 (3)C30—H30A0.9300
O9—C521.138 (3)C31—H31A0.9300
C1—C61.373 (3)C32—C371.381 (3)
C1—C21.374 (3)C32—C331.396 (3)
C2—C31.386 (4)C33—C341.383 (3)
C2—H2A0.9300C33—H33A0.9300
C3—C41.364 (4)C34—C351.367 (4)
C3—H3A0.9300C34—H34A0.9300
C4—C51.357 (4)C35—C361.358 (4)
C4—H4A0.9300C36—C371.388 (3)
C5—C61.386 (3)C36—H36A0.9300
C5—H5A0.9300C37—H37A0.9300
C6—H6A0.9300C38—C431.387 (3)
C7—C81.369 (3)C38—C391.395 (3)
C7—C121.387 (3)C39—C401.384 (3)
C8—C91.382 (4)C39—H39A0.9300
C8—H8A0.9300C40—C411.369 (4)
C9—C101.371 (4)C40—H40A0.9300
C9—H9A0.9300C41—C421.349 (4)
C10—C111.358 (4)C42—C431.383 (3)
C10—H10A0.9300C42—H42A0.9300
C11—C121.379 (3)C43—H43A0.9300
C45—Ru1—C4491.54 (10)As1—C13—H13B108.9
C45—Ru1—C4691.41 (10)As2—C13—H13B108.9
C44—Ru1—C46175.72 (9)H13A—C13—H13B107.7
C45—Ru1—As1100.14 (7)C15—C14—C19118.5 (2)
C44—Ru1—As189.90 (7)C15—C14—As2118.58 (17)
C46—Ru1—As192.63 (7)C19—C14—As2122.92 (17)
C45—Ru1—Ru2166.13 (7)C14—C15—C16120.6 (3)
C44—Ru1—Ru281.39 (7)C14—C15—H15A119.7
C46—Ru1—Ru295.07 (7)C16—C15—H15A119.7
As1—Ru1—Ru291.810 (7)C17—C16—C15120.4 (3)
C45—Ru1—Ru3110.63 (7)C17—C16—H16A119.8
C44—Ru1—Ru399.93 (6)C15—C16—H16A119.8
C46—Ru1—Ru376.12 (7)C18—C17—C16119.5 (3)
As1—Ru1—Ru3147.251 (9)C18—C17—H17A120.3
Ru2—Ru1—Ru359.460 (5)C16—C17—H17A120.3
C48—Ru2—C4793.55 (10)C17—C18—C19120.3 (3)
C48—Ru2—C4989.56 (10)C17—C18—H18A119.8
C47—Ru2—C49175.70 (9)C19—C18—H18A119.8
C48—Ru2—As2102.41 (7)C18—C19—C14120.6 (2)
C47—Ru2—As288.86 (6)C18—C19—H19A119.7
C49—Ru2—As293.37 (6)C14—C19—H19A119.7
C48—Ru2—Ru3100.99 (7)C21—C20—C25119.2 (2)
C47—Ru2—Ru389.69 (6)C21—C20—As2121.3 (2)
C49—Ru2—Ru386.80 (6)C25—C20—As2119.48 (19)
As2—Ru2—Ru3156.606 (9)C20—C21—C22120.0 (4)
C48—Ru2—Ru1161.07 (7)C20—C21—H21A120.0
C47—Ru2—Ru182.33 (6)C22—C21—H21A120.0
C49—Ru2—Ru193.77 (7)C23—C22—C21120.6 (4)
As2—Ru2—Ru195.997 (7)C23—C22—H22A119.7
Ru3—Ru2—Ru160.687 (6)C21—C22—H22A119.7
C51—Ru3—C50100.53 (10)C22—C23—C24120.6 (3)
C51—Ru3—C5293.07 (10)C22—C23—H23A119.7
C50—Ru3—C52166.40 (10)C24—C23—H23A119.7
C51—Ru3—P198.01 (7)C23—C24—C25118.7 (4)
C50—Ru3—P187.86 (7)C23—C24—H24A120.6
C52—Ru3—P190.09 (6)C25—C24—H24A120.6
C51—Ru3—Ru286.13 (7)C20—C25—C24120.8 (3)
C50—Ru3—Ru291.60 (7)C20—C25—H25A119.6
C52—Ru3—Ru289.48 (6)C24—C25—H25A119.6
P1—Ru3—Ru2175.856 (15)C27—C26—C31118.3 (2)
C51—Ru3—Ru1143.71 (7)C27—C26—P1124.42 (19)
C50—Ru3—Ru170.56 (7)C31—C26—P1117.28 (18)
C52—Ru3—Ru198.46 (6)C26—C27—C28121.2 (3)
P1—Ru3—Ru1116.158 (15)C26—C27—H27A119.4
Ru2—Ru3—Ru159.854 (5)C28—C27—H27A119.4
C7—As1—C199.13 (9)C29—C28—C27118.3 (3)
C7—As1—C13105.49 (9)C29—C28—H28A120.9
C1—As1—C13100.42 (8)C27—C28—H28A120.9
C7—As1—Ru1117.21 (6)C28—C29—C30123.1 (3)
C1—As1—Ru1117.69 (7)C28—C29—F1118.6 (3)
C13—As1—Ru1114.45 (6)C30—C29—F1118.3 (3)
C20—As2—C14103.52 (10)C29—C30—C31118.5 (3)
C20—As2—C13100.82 (9)C29—C30—H30A120.8
C14—As2—C13104.04 (9)C31—C30—H30A120.8
C20—As2—Ru2116.82 (6)C30—C31—C26120.7 (3)
C14—As2—Ru2115.38 (6)C30—C31—H31A119.6
C13—As2—Ru2114.36 (6)C26—C31—H31A119.6
C38—P1—C26104.67 (10)C37—C32—C33118.2 (2)
C38—P1—C32103.13 (10)C37—C32—P1121.90 (16)
C26—P1—C32100.23 (10)C33—C32—P1119.87 (17)
C38—P1—Ru3113.52 (7)C34—C33—C32120.8 (2)
C26—P1—Ru3116.15 (7)C34—C33—H33A119.6
C32—P1—Ru3117.26 (7)C32—C33—H33A119.6
C6—C1—C2118.6 (2)C35—C34—C33118.5 (2)
C6—C1—As1119.56 (16)C35—C34—H34A120.7
C2—C1—As1121.83 (18)C33—C34—H34A120.7
C1—C2—C3120.3 (3)F2—C35—C36119.0 (3)
C1—C2—H2A119.8F2—C35—C34118.3 (2)
C3—C2—H2A119.8C36—C35—C34122.7 (2)
C4—C3—C2120.3 (3)C35—C36—C37118.4 (2)
C4—C3—H3A119.8C35—C36—H36A120.8
C2—C3—H3A119.8C37—C36—H36A120.8
C5—C4—C3119.9 (3)C32—C37—C36121.3 (2)
C5—C4—H4A120.1C32—C37—H37A119.4
C3—C4—H4A120.1C36—C37—H37A119.4
C4—C5—C6120.1 (3)C43—C38—C39118.2 (2)
C4—C5—H5A119.9C43—C38—P1121.32 (17)
C6—C5—H5A119.9C39—C38—P1120.17 (17)
C1—C6—C5120.7 (2)C40—C39—C38121.2 (2)
C1—C6—H6A119.6C40—C39—H39A119.4
C5—C6—H6A119.6C38—C39—H39A119.4
C8—C7—C12118.8 (2)C41—C40—C39117.7 (2)
C8—C7—As1124.98 (16)C41—C40—H40A121.1
C12—C7—As1116.15 (17)C39—C40—H40A121.1
C7—C8—C9120.2 (2)C42—C41—F3118.7 (3)
C7—C8—H8A119.9C42—C41—C40123.2 (2)
C9—C8—H8A119.9F3—C41—C40118.1 (3)
C10—C9—C8120.4 (3)C41—C42—C43119.0 (2)
C10—C9—H9A119.8C41—C42—H42A120.5
C8—C9—H9A119.8C43—C42—H42A120.5
C11—C10—C9119.9 (3)C42—C43—C38120.7 (2)
C11—C10—H10A120.0C42—C43—H43A119.7
C9—C10—H10A120.0C38—C43—H43A119.7
C10—C11—C12120.0 (3)O1—C44—Ru1173.5 (2)
C10—C11—H11A120.0O2—C45—Ru1176.6 (2)
C12—C11—H11A120.0O3—C46—Ru1170.8 (2)
C11—C12—C7120.6 (2)O4—C47—Ru2174.32 (19)
C11—C12—H12A119.7O5—C48—Ru2178.3 (2)
C7—C12—H12A119.7O6—C49—Ru2174.7 (2)
As1—C13—As2113.22 (9)O7—C50—Ru3169.1 (2)
As1—C13—H13A108.9O8—C51—Ru3177.4 (2)
As2—C13—H13A108.9O9—C52—Ru3174.4 (2)
C45—Ru1—Ru2—C4862.5 (4)C7—As1—C1—C2−22.1 (2)
C44—Ru1—Ru2—C48122.5 (3)C13—As1—C1—C285.6 (2)
C46—Ru1—Ru2—C48−55.1 (3)Ru1—As1—C1—C2−149.55 (18)
As1—Ru1—Ru2—C48−147.9 (2)C6—C1—C2—C3−1.1 (4)
Ru3—Ru1—Ru2—C4815.5 (2)As1—C1—C2—C3178.6 (2)
C45—Ru1—Ru2—C47140.9 (3)C1—C2—C3—C41.3 (5)
C44—Ru1—Ru2—C47−159.06 (9)C2—C3—C4—C5−0.7 (5)
C46—Ru1—Ru2—C4723.38 (10)C3—C4—C5—C6−0.1 (5)
As1—Ru1—Ru2—C47−69.43 (6)C2—C1—C6—C50.3 (4)
Ru3—Ru1—Ru2—C4793.98 (6)As1—C1—C6—C5−179.4 (2)
C45—Ru1—Ru2—C49−37.3 (3)C4—C5—C6—C10.3 (4)
C44—Ru1—Ru2—C4922.77 (9)C1—As1—C7—C8110.6 (2)
C46—Ru1—Ru2—C49−154.80 (10)C13—As1—C7—C87.0 (2)
As1—Ru1—Ru2—C49112.40 (6)Ru1—As1—C7—C8−121.69 (19)
Ru3—Ru1—Ru2—C49−84.19 (6)C1—As1—C7—C12−65.70 (19)
C45—Ru1—Ru2—As2−131.0 (3)C13—As1—C7—C12−169.26 (18)
C44—Ru1—Ru2—As2−71.02 (7)Ru1—As1—C7—C1262.03 (19)
C46—Ru1—Ru2—As2111.41 (7)C12—C7—C8—C91.7 (4)
As1—Ru1—Ru2—As218.605 (9)As1—C7—C8—C9−174.5 (2)
Ru3—Ru1—Ru2—As2−177.986 (9)C7—C8—C9—C10−0.2 (5)
C45—Ru1—Ru2—Ru346.9 (3)C8—C9—C10—C11−1.4 (5)
C44—Ru1—Ru2—Ru3106.96 (7)C9—C10—C11—C121.4 (5)
C46—Ru1—Ru2—Ru3−70.61 (7)C10—C11—C12—C70.1 (5)
As1—Ru1—Ru2—Ru3−163.409 (9)C8—C7—C12—C11−1.7 (4)
C48—Ru2—Ru3—C5118.29 (11)As1—C7—C12—C11174.8 (2)
C47—Ru2—Ru3—C51111.85 (10)C7—As1—C13—As2−96.54 (12)
C49—Ru2—Ru3—C51−70.64 (10)C1—As1—C13—As2160.85 (11)
As2—Ru2—Ru3—C51−161.73 (8)Ru1—As1—C13—As233.79 (13)
Ru1—Ru2—Ru3—C51−166.78 (7)C20—As2—C13—As1−141.78 (12)
C48—Ru2—Ru3—C50118.73 (11)C14—As2—C13—As1111.17 (11)
C47—Ru2—Ru3—C50−147.71 (9)Ru2—As2—C13—As1−15.57 (13)
C49—Ru2—Ru3—C5029.80 (10)C20—As2—C14—C15104.4 (2)
As2—Ru2—Ru3—C50−61.29 (7)C13—As2—C14—C15−150.6 (2)
Ru1—Ru2—Ru3—C50−66.34 (7)Ru2—As2—C14—C15−24.5 (2)
C48—Ru2—Ru3—C52−74.83 (11)C20—As2—C14—C19−77.1 (2)
C47—Ru2—Ru3—C5218.73 (9)C13—As2—C14—C1927.9 (2)
C49—Ru2—Ru3—C52−163.76 (10)Ru2—As2—C14—C19154.01 (16)
As2—Ru2—Ru3—C52105.15 (7)C19—C14—C15—C16−0.8 (4)
Ru1—Ru2—Ru3—C52100.10 (7)As2—C14—C15—C16177.8 (3)
C48—Ru2—Ru3—Ru1−174.93 (8)C14—C15—C16—C17−1.0 (5)
C47—Ru2—Ru3—Ru1−81.37 (7)C15—C16—C17—C181.6 (5)
C49—Ru2—Ru3—Ru196.14 (7)C16—C17—C18—C19−0.5 (5)
As2—Ru2—Ru3—Ru15.05 (2)C17—C18—C19—C14−1.3 (4)
C45—Ru1—Ru3—C51−146.55 (15)C15—C14—C19—C181.9 (4)
C44—Ru1—Ru3—C51−51.09 (14)As2—C14—C19—C18−176.55 (19)
C46—Ru1—Ru3—C51127.24 (14)C14—As2—C20—C21−19.8 (2)
As1—Ru1—Ru3—C5154.51 (12)C13—As2—C20—C21−127.3 (2)
Ru2—Ru1—Ru3—C5122.67 (12)Ru2—As2—C20—C21108.2 (2)
C45—Ru1—Ru3—C50−65.37 (11)C14—As2—C20—C25162.3 (2)
C44—Ru1—Ru3—C5030.08 (10)C13—As2—C20—C2554.8 (2)
C46—Ru1—Ru3—C50−151.59 (10)Ru2—As2—C20—C25−69.7 (2)
As1—Ru1—Ru3—C50135.69 (7)C25—C20—C21—C22−0.8 (4)
Ru2—Ru1—Ru3—C50103.84 (7)As2—C20—C21—C22−178.7 (3)
C45—Ru1—Ru3—C52106.35 (10)C20—C21—C22—C230.4 (6)
C44—Ru1—Ru3—C52−158.19 (10)C21—C22—C23—C24−0.2 (7)
C46—Ru1—Ru3—C5220.14 (10)C22—C23—C24—C250.4 (7)
As1—Ru1—Ru3—C52−52.59 (7)C21—C20—C25—C241.0 (4)
Ru2—Ru1—Ru3—C52−84.43 (7)As2—C20—C25—C24179.0 (2)
C45—Ru1—Ru3—P112.06 (8)C23—C24—C25—C20−0.8 (5)
C44—Ru1—Ru3—P1107.52 (7)C38—P1—C26—C27−3.9 (2)
C46—Ru1—Ru3—P1−74.15 (7)C32—P1—C26—C27102.7 (2)
As1—Ru1—Ru3—P1−146.88 (2)Ru3—P1—C26—C27−129.9 (2)
Ru2—Ru1—Ru3—P1−178.723 (18)C38—P1—C26—C31178.21 (18)
C45—Ru1—Ru3—Ru2−169.22 (8)C32—P1—C26—C31−75.17 (19)
C44—Ru1—Ru3—Ru2−73.76 (7)Ru3—P1—C26—C3152.2 (2)
C46—Ru1—Ru3—Ru2104.57 (7)C31—C26—C27—C28−1.5 (4)
As1—Ru1—Ru3—Ru231.841 (15)P1—C26—C27—C28−179.4 (2)
C45—Ru1—As1—C7−94.36 (10)C26—C27—C28—C291.1 (5)
C44—Ru1—As1—C7174.09 (9)C27—C28—C29—C30−0.1 (5)
C46—Ru1—As1—C7−2.46 (9)C27—C28—C29—F1179.8 (3)
Ru2—Ru1—As1—C792.71 (7)C28—C29—C30—C31−0.4 (5)
Ru3—Ru1—As1—C765.67 (7)F1—C29—C30—C31179.6 (2)
C45—Ru1—As1—C123.77 (10)C29—C30—C31—C260.0 (4)
C44—Ru1—As1—C1−67.78 (9)C27—C26—C31—C300.9 (4)
C46—Ru1—As1—C1115.67 (9)P1—C26—C31—C30179.0 (2)
Ru2—Ru1—As1—C1−149.17 (7)C38—P1—C32—C37−114.8 (2)
Ru3—Ru1—As1—C1−176.21 (7)C26—P1—C32—C37137.4 (2)
C45—Ru1—As1—C13141.34 (10)Ru3—P1—C32—C3710.7 (2)
C44—Ru1—As1—C1349.79 (10)C38—P1—C32—C3363.4 (2)
C46—Ru1—As1—C13−126.76 (10)C26—P1—C32—C33−44.4 (2)
Ru2—Ru1—As1—C13−31.59 (7)Ru3—P1—C32—C33−171.08 (16)
Ru3—Ru1—As1—C13−58.63 (7)C37—C32—C33—C340.0 (4)
C48—Ru2—As2—C20−72.35 (12)P1—C32—C33—C34−178.2 (2)
C47—Ru2—As2—C20−165.73 (11)C32—C33—C34—C350.4 (4)
C49—Ru2—As2—C2017.94 (11)C33—C34—C35—F2179.5 (3)
Ru3—Ru2—As2—C20107.67 (9)C33—C34—C35—C36−0.6 (5)
Ru1—Ru2—As2—C20112.10 (9)F2—C35—C36—C37−179.7 (3)
C48—Ru2—As2—C1449.64 (11)C34—C35—C36—C370.4 (4)
C47—Ru2—As2—C14−43.74 (9)C33—C32—C37—C36−0.2 (4)
C49—Ru2—As2—C14139.93 (10)P1—C32—C37—C36178.0 (2)
Ru3—Ru2—As2—C14−130.34 (7)C35—C36—C37—C320.0 (4)
Ru1—Ru2—As2—C14−125.91 (7)C26—P1—C38—C43127.61 (17)
C48—Ru2—As2—C13170.28 (11)C32—P1—C38—C4323.16 (19)
C47—Ru2—As2—C1376.90 (10)Ru3—P1—C38—C43−104.75 (16)
C49—Ru2—As2—C13−99.43 (10)C26—P1—C38—C39−59.03 (19)
Ru3—Ru2—As2—C13−9.70 (8)C32—P1—C38—C39−163.47 (17)
Ru1—Ru2—As2—C13−5.27 (7)Ru3—P1—C38—C3968.62 (18)
C51—Ru3—P1—C38162.57 (11)C43—C38—C39—C40−1.8 (3)
C50—Ru3—P1—C3862.24 (10)P1—C38—C39—C40−175.41 (18)
C52—Ru3—P1—C38−104.31 (10)C38—C39—C40—C411.0 (4)
Ru1—Ru3—P1—C38−4.83 (8)C39—C40—C41—C420.6 (4)
C51—Ru3—P1—C26−76.00 (11)C39—C40—C41—F3178.7 (2)
C50—Ru3—P1—C26−176.34 (11)F3—C41—C42—C43−179.3 (2)
C52—Ru3—P1—C2617.11 (11)C40—C41—C42—C43−1.2 (4)
Ru1—Ru3—P1—C26116.59 (9)C41—C42—C43—C380.3 (3)
C51—Ru3—P1—C3242.38 (11)C39—C38—C43—C421.2 (3)
C50—Ru3—P1—C32−57.95 (10)P1—C38—C43—C42174.69 (16)
C52—Ru3—P1—C32135.50 (10)C51—Ru3—C50—O7−60.1 (11)
Ru1—Ru3—P1—C32−125.03 (8)C52—Ru3—C50—O7119.1 (11)
C7—As1—C1—C6157.51 (19)P1—Ru3—C50—O737.6 (11)
C13—As1—C1—C6−94.8 (2)Ru2—Ru3—C50—O7−146.5 (11)
Ru1—As1—C1—C630.1 (2)Ru1—Ru3—C50—O7156.4 (11)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C23—H23A···F3i0.932.463.337 (5)157
C34—H34A···O3ii0.932.583.405 (3)148
C42—H42A···O2iii0.932.523.438 (3)167
C11—H11A···Cg1iv0.932.943.767 (3)149
C28—H28A···Cg2ii0.932.893.807 (3)168
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y, −z; (iv) −x+1, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C23—H23A···F3i0.932.463.337 (5)157
C34—H34A···O3ii0.932.583.405 (3)148
C42—H42A···O2iii0.932.523.438 (3)167
C11—H11A···Cg1iv0.932.943.767 (3)149
C28—H28A···Cg2ii0.932.893.807 (3)168
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y, −z; (iv) −x+1, y−1/2, −z+1/2.
Acknowledgements top

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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