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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): m864.
Published online 2010 June 30. doi:  10.1107/S1600536810021513
PMCID: PMC3006820

Azido­(benzonitrile-κN)[hydrido­tris(pyrazol-1-yl-κN 2)borato](triphenyl­phosphine-κP)ruthenium(II)

Abstract

Facile ligand substitution is observed when the ruthenium–azide complex, [RuN3(Tp)(PPh3)2] [Tp,HB(pz)3, pz = pyrazol­yl, PPh3 = triphenyl­phosphine] is treated with benzo­nitrile, yielding the title compound, [Ru(C9H10BN6)(N3)(C7H5N)(C18H15P)]. The asymmetric unit contains two crystallographically independent mol­ecules. In each one, the RuII atom is six-coordinated in a distorted octa­hedral geometry by five N atoms from an htpb ligand, an azide ligand and a benzonitrile ligand and one P atom from a triphenyl­phosphine (tpp) ligand. The azide group is almost linear and is coordinated to Ru with an average Ru—N—N angle of 124.9 (3)°.

Related literature

For general background to azide and triazole compounds, see: Dori & Ziolo (1973 [triangle]); Huynh et al. (2003 [triangle]); Krivopalov & Shkurko (2005 [triangle]); Meyer et al. (1998 [triangle]); Padwa (1976 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m864-scheme1.jpg

Experimental

Crystal data

  • [Ru(C9H10BN6)(N3)(C7H5N)(C18H15P)]
  • M r = 721.53
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m864-efi1.jpg
  • a = 11.1888 (2) Å
  • b = 16.2588 (3) Å
  • c = 18.9944 (4) Å
  • α = 109.588 (1)°
  • β = 91.930 (1)°
  • γ = 90.823 (1)°
  • V = 3252.37 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.57 mm−1
  • T = 200 K
  • 0.20 × 0.08 × 0.03 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 [triangle]) T min = 0.894, T max = 0.983
  • 28844 measured reflections
  • 11501 independent reflections
  • 8347 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.093
  • S = 1.01
  • 11501 reflections
  • 847 parameters
  • H-atom parameters constrained
  • Δρmax = 0.56 e Å−3
  • Δρmin = −0.48 e Å−3

Data collection: COLLECT (Nonius, 1998 [triangle]); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021513/hy2311sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021513/hy2311Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We gratefully acknowledge financial support in part from the National Science Council, Taiwan (NSC 97-2113-M-133-001-MY2) and in part from the project of specific research fields in Tatung University, Taiwan (B96–C07-081). We also thank Mr Ting Shen Kuo (Department of Chemistry, National Taiwan Normal University) for his assistance with the X-ray single crystal structure analysis and the project of specific research fields in Chung Yuan Christian University, Taiwan, under grant CYCU-98-CR–CH.

supplementary crystallographic information

Comment

Organic azides are synthetically helpful reagents. Amongst many transformations, perhaps the most important one is the 1,3-dipolar cycloaddition reactions with alkynes to synthesize triazoles (Padwa, 1976). Triazoles are nitrogen heteroarenes, which have found a range of significant applications in pharmaceutical and agricultural industries (Krivopalov & Shkurko, 2005). On the other hand, the azide anion, N3- , is a versatile ligand because it shows a variety of coordination modes, e.g. end-on monodentate, one-end bridging and end-to-end bridging modes, and also because its complexes exhibit interesting thermal and photochemical reactivities (Dori & Ziolo, 1973; Huynh et al., 2003; Meyer et al., 1998).

The title compound contains two crystallographically distinct molecules (Fig. 1, Table 1). The azide groups are almost linear [N8—N9—N10 = 176.8 (4), N18—N19—N20 = 175.7 (4)°] and are coordinated to Ru with Ru—N—N angles of 123.8 (3) and 125.9 (3)°. There is a small difference between the N—N distances [1.172 (4), 1.188 (4) and 1.173 (4), 1.172 (4) Å]. The Ru1—N7 and N7—C28 bond lengths of 1.983 (3) and 1.150 (4) Å correspond to a single Ru—N bond and a C[equivalent]N bond. The N7—C28—C29 of angle 179.0 (4)° indicates an sp hybridization as expected.

Experimental

To a solution of [RuN3(htpb)(tpp)2] (htpb = hydridotripyrazolylborate, tpp = triphenylphosphine) in 30 ml of THF was added 10 ml of PhCN. The solution was stirred for 22 h, with color changed from yellow to orange-yellow, and then the solution was filtered through Celite. The solvent of the filtrate was removed under vacuum, and the residue was washed with n-hexane to give the title compound. The bright-yellow crystals of the title compound for X-ray structure analysis were obtained by slow diffusion of diethyl ether into a CH2Cl2 solution of the title compound at 0°C for 3 d.

Refinement

H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H = 0.95 and B—H = 1.00 Å and Uiso(H) = 1.2Ueq(C, B).

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

[Ru(C9H10BN6)(N3)(C7H5N)(C18H15P)]Z = 4
Mr = 721.53F(000) = 1472
Triclinic, P1Dx = 1.474 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.1888 (2) ÅCell parameters from 5430 reflections
b = 16.2588 (3) Åθ = 2.7–25.0°
c = 18.9944 (4) ŵ = 0.57 mm1
α = 109.588 (1)°T = 200 K
β = 91.930 (1)°Prism, yellow
γ = 90.823 (1)°0.20 × 0.08 × 0.03 mm
V = 3252.37 (11) Å3

Data collection

Nonius KappaCCD diffractometer11501 independent reflections
Radiation source: fine-focus sealed tube8347 reflections with I > 2σ(I)
graphiteRint = 0.049
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 1.1°
ω and [var phi] scansh = −13→13
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)k = −14→19
Tmin = 0.894, Tmax = 0.983l = −22→22
28844 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0383P)2 + 0.0352P] where P = (Fo2 + 2Fc2)/3
11501 reflections(Δ/σ)max = 0.001
847 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = −0.48 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
B10.6242 (4)0.5295 (3)0.2622 (3)0.0396 (12)
H1'0.57580.47500.23560.048*
B20.8881 (4)0.5283 (3)0.7621 (3)0.0353 (11)
H2'0.93550.47540.73760.042*
C10.8553 (3)0.6230 (3)0.1793 (2)0.0350 (10)
H10.91650.66540.18250.042*
C20.8230 (4)0.5530 (3)0.1152 (2)0.0454 (11)
H20.85580.53870.06720.054*
C30.7325 (4)0.5088 (3)0.1369 (2)0.0428 (11)
H30.69090.45750.10570.051*
C40.8330 (4)0.5572 (3)0.4207 (2)0.0406 (11)
H40.89240.58930.45680.049*
C50.7939 (4)0.4732 (3)0.4112 (2)0.0495 (12)
H50.82010.43760.43910.059*
C60.7100 (4)0.4515 (3)0.3535 (2)0.0460 (11)
H60.66720.39720.33360.055*
C70.5004 (3)0.7446 (3)0.3399 (2)0.0356 (10)
H70.50720.80600.36430.043*
C80.3939 (3)0.6988 (3)0.3114 (2)0.0453 (12)
H80.31630.72190.31240.054*
C90.4244 (3)0.6135 (3)0.2816 (2)0.0439 (11)
H90.37090.56550.25780.053*
C100.6223 (3)0.7708 (2)0.5168 (2)0.0276 (9)
C110.5806 (3)0.8369 (3)0.5780 (2)0.0407 (10)
H110.61940.89280.59430.049*
C120.4826 (4)0.8216 (3)0.6155 (3)0.0484 (12)
H120.45510.86700.65740.058*
C130.4256 (3)0.7412 (3)0.5921 (3)0.0473 (12)
H130.35900.73080.61790.057*
C140.4647 (3)0.6759 (3)0.5314 (2)0.0448 (11)
H140.42420.62060.51490.054*
C150.5639 (3)0.6901 (3)0.4936 (2)0.0368 (10)
H150.59110.64420.45200.044*
C160.8749 (3)0.7677 (2)0.5389 (2)0.0255 (8)
C170.9956 (3)0.7738 (3)0.5255 (2)0.0375 (10)
H171.01840.78980.48400.045*
C181.0829 (3)0.7568 (3)0.5716 (2)0.0444 (11)
H181.16500.76330.56280.053*
C191.0514 (3)0.7305 (3)0.6305 (2)0.0423 (11)
H191.11140.71820.66180.051*
C200.9336 (3)0.7222 (3)0.6434 (2)0.0389 (10)
H200.91170.70330.68350.047*
C210.8452 (3)0.7411 (2)0.5985 (2)0.0329 (9)
H210.76350.73580.60870.039*
C220.7704 (3)0.9056 (2)0.4965 (2)0.0312 (9)
C230.8647 (3)0.9581 (3)0.5366 (2)0.0403 (10)
H230.92980.93270.55450.048*
C240.8653 (4)1.0487 (3)0.5513 (3)0.0512 (12)
H240.93141.08380.57830.061*
C250.7734 (4)1.0862 (3)0.5275 (3)0.0564 (13)
H250.77411.14770.53840.068*
C260.6797 (5)1.0362 (3)0.4877 (3)0.0626 (15)
H260.61521.06300.47060.075*
C270.6769 (4)0.9461 (3)0.4717 (3)0.0546 (13)
H270.61070.91200.44370.066*
C280.7948 (3)0.8687 (3)0.2999 (2)0.0340 (9)
C290.8049 (3)0.9435 (3)0.2768 (2)0.0352 (10)
C300.7032 (4)0.9777 (3)0.2551 (3)0.0586 (14)
H300.62700.95220.25710.070*
C310.7110 (5)1.0477 (3)0.2310 (3)0.0637 (15)
H310.64051.07030.21590.076*
C320.8192 (5)1.0851 (3)0.2286 (3)0.0668 (15)
H320.82411.13400.21190.080*
C330.9201 (5)1.0533 (3)0.2497 (3)0.0781 (17)
H330.99551.07970.24750.094*
C340.9145 (4)0.9819 (3)0.2750 (3)0.0575 (13)
H340.98530.96020.29060.069*
C350.6565 (3)0.6144 (3)0.6709 (2)0.0355 (10)
H350.59640.65530.67170.043*
C360.6849 (4)0.5451 (3)0.6086 (2)0.0480 (11)
H360.65000.53020.55950.058*
C370.7734 (4)0.5024 (3)0.6324 (2)0.0459 (11)
H370.81120.45130.60240.055*
C381.0176 (3)0.7460 (3)0.8471 (2)0.0349 (10)
H381.01240.80690.87270.042*
C391.1234 (3)0.7041 (3)0.8214 (2)0.0413 (11)
H391.20150.72940.82560.050*
C401.0891 (3)0.6182 (3)0.7887 (2)0.0397 (11)
H401.14110.57190.76570.048*
C410.6899 (3)0.5506 (2)0.9147 (2)0.0310 (9)
H410.63150.58070.94830.037*
C420.7323 (3)0.4688 (3)0.9094 (2)0.0378 (10)
H420.71110.43380.93840.045*
C430.8113 (3)0.4499 (3)0.8530 (2)0.0370 (10)
H430.85480.39770.83530.044*
C440.6426 (3)0.7564 (2)1.0298 (2)0.0268 (8)
C450.5213 (3)0.7460 (3)1.0065 (2)0.0384 (10)
H450.49590.75690.96230.046*
C460.4381 (3)0.7198 (3)1.0481 (2)0.0469 (12)
H460.35630.71181.03160.056*
C470.4734 (4)0.7054 (3)1.1133 (2)0.0436 (11)
H470.41640.68721.14140.052*
C480.5904 (3)0.7175 (3)1.1369 (2)0.0416 (11)
H480.61480.70841.18210.050*
C490.6745 (3)0.7428 (3)1.0960 (2)0.0352 (10)
H490.75570.75101.11360.042*
C500.8942 (3)0.7713 (2)1.0188 (2)0.0282 (9)
C510.9526 (3)0.6919 (2)0.9966 (2)0.0313 (9)
H510.92220.64480.95460.038*
C521.0545 (3)0.6817 (3)1.0357 (2)0.0394 (10)
H521.09360.62741.02030.047*
C531.1003 (3)0.7491 (3)1.0967 (2)0.0434 (11)
H531.17070.74171.12310.052*
C541.0427 (4)0.8275 (3)1.1190 (2)0.0483 (12)
H541.07340.87431.16110.058*
C550.9406 (3)0.8385 (3)1.0806 (2)0.0381 (10)
H550.90160.89281.09670.046*
C560.7436 (3)0.8994 (2)0.9921 (2)0.0271 (8)
C570.6509 (4)0.9475 (3)1.0291 (2)0.0450 (11)
H570.58750.91871.04430.054*
C580.6477 (4)1.0375 (3)1.0450 (3)0.0584 (14)
H580.58311.06931.07150.070*
C590.7375 (4)1.0806 (3)1.0225 (2)0.0468 (11)
H590.73531.14191.03290.056*
C600.8305 (4)1.0334 (3)0.9845 (3)0.0518 (13)
H600.89351.06210.96880.062*
C610.8321 (3)0.9440 (3)0.9694 (3)0.0441 (11)
H610.89620.91210.94250.053*
C620.7215 (3)0.8628 (3)0.7954 (2)0.0313 (9)
C630.6984 (3)0.9433 (3)0.7822 (2)0.0338 (9)
C640.6199 (4)0.9992 (3)0.8289 (3)0.0504 (12)
H640.58360.98360.86730.060*
C650.5950 (4)1.0775 (3)0.8194 (3)0.0603 (14)
H650.53921.11520.85020.072*
C660.6503 (4)1.1015 (3)0.7655 (3)0.0512 (12)
H660.63381.15620.75980.061*
C670.7275 (4)1.0481 (3)0.7207 (2)0.0464 (11)
H670.76441.06500.68320.056*
C680.7543 (4)0.9678 (3)0.7286 (2)0.0434 (11)
H680.81020.93070.69740.052*
N10.7875 (3)0.6218 (2)0.23571 (17)0.0298 (7)
N20.7132 (3)0.5507 (2)0.20954 (18)0.0345 (8)
N30.7748 (3)0.5870 (2)0.37157 (17)0.0307 (8)
N40.6987 (3)0.5207 (2)0.32976 (18)0.0361 (8)
N50.5921 (2)0.6903 (2)0.32828 (17)0.0295 (7)
N60.5438 (3)0.6089 (2)0.29169 (18)0.0356 (8)
N70.7850 (2)0.8086 (2)0.31847 (17)0.0285 (7)
N80.9664 (3)0.7047 (2)0.35704 (19)0.0387 (9)
N91.0281 (3)0.7336 (2)0.3220 (2)0.0391 (8)
N101.0951 (3)0.7611 (3)0.2875 (2)0.0607 (11)
N110.7258 (2)0.6156 (2)0.73002 (17)0.0291 (7)
N120.7979 (3)0.5453 (2)0.70548 (18)0.0324 (8)
N130.9242 (2)0.6894 (2)0.83116 (17)0.0279 (7)
N140.9701 (2)0.6093 (2)0.79404 (17)0.0300 (7)
N150.7429 (2)0.58089 (19)0.86601 (16)0.0270 (7)
N160.8175 (2)0.5169 (2)0.82667 (18)0.0307 (7)
N170.7334 (2)0.8024 (2)0.81263 (17)0.0288 (7)
N180.5513 (3)0.6914 (2)0.83975 (18)0.0355 (8)
N190.4879 (3)0.7312 (2)0.81356 (19)0.0370 (8)
N200.4184 (3)0.7681 (3)0.7884 (3)0.0688 (13)
P10.76176 (8)0.78578 (6)0.47329 (5)0.0251 (2)
P20.75346 (8)0.78065 (6)0.96896 (5)0.0242 (2)
Ru10.77697 (2)0.703233 (19)0.348879 (17)0.02482 (9)
Ru20.73983 (2)0.697064 (19)0.842995 (16)0.02291 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
B10.049 (3)0.036 (3)0.032 (3)−0.006 (2)0.001 (2)0.011 (2)
B20.039 (2)0.030 (3)0.038 (3)0.007 (2)0.003 (2)0.013 (2)
C10.037 (2)0.043 (3)0.030 (2)0.0103 (19)0.0069 (18)0.017 (2)
C20.055 (3)0.056 (3)0.026 (3)0.016 (2)0.009 (2)0.014 (2)
C30.060 (3)0.035 (3)0.029 (3)0.009 (2)−0.006 (2)0.006 (2)
C40.058 (3)0.038 (3)0.031 (3)0.022 (2)0.007 (2)0.017 (2)
C50.086 (3)0.029 (3)0.041 (3)0.016 (2)0.010 (3)0.020 (2)
C60.071 (3)0.031 (3)0.046 (3)0.008 (2)0.018 (2)0.022 (2)
C70.037 (2)0.040 (3)0.032 (2)0.0067 (19)−0.0003 (18)0.015 (2)
C80.029 (2)0.068 (3)0.046 (3)0.004 (2)0.0015 (19)0.029 (3)
C90.034 (2)0.057 (3)0.044 (3)−0.018 (2)−0.0098 (19)0.023 (2)
C100.0270 (19)0.032 (2)0.025 (2)0.0027 (17)−0.0008 (16)0.0111 (19)
C110.038 (2)0.040 (3)0.040 (3)0.0025 (19)0.0050 (19)0.008 (2)
C120.044 (2)0.058 (3)0.045 (3)0.015 (2)0.020 (2)0.018 (3)
C130.030 (2)0.073 (4)0.052 (3)0.004 (2)0.009 (2)0.039 (3)
C140.041 (2)0.054 (3)0.043 (3)−0.012 (2)0.002 (2)0.022 (3)
C150.040 (2)0.041 (3)0.031 (2)−0.0008 (19)0.0042 (18)0.014 (2)
C160.0306 (19)0.021 (2)0.024 (2)0.0014 (16)−0.0003 (16)0.0071 (17)
C170.035 (2)0.048 (3)0.036 (3)0.0012 (19)0.0014 (18)0.022 (2)
C180.030 (2)0.064 (3)0.042 (3)0.004 (2)−0.0005 (19)0.022 (3)
C190.044 (2)0.046 (3)0.040 (3)0.010 (2)−0.011 (2)0.020 (2)
C200.044 (2)0.046 (3)0.037 (3)0.004 (2)−0.0021 (19)0.028 (2)
C210.037 (2)0.035 (2)0.030 (2)0.0058 (18)0.0060 (17)0.015 (2)
C220.035 (2)0.029 (2)0.030 (2)0.0019 (18)0.0069 (17)0.0103 (19)
C230.039 (2)0.039 (3)0.043 (3)−0.001 (2)0.008 (2)0.014 (2)
C240.055 (3)0.033 (3)0.065 (4)−0.004 (2)0.016 (2)0.015 (3)
C250.075 (3)0.032 (3)0.068 (4)0.007 (3)0.025 (3)0.022 (3)
C260.080 (4)0.044 (3)0.070 (4)0.028 (3)0.002 (3)0.027 (3)
C270.063 (3)0.032 (3)0.063 (3)0.008 (2)−0.018 (2)0.011 (2)
C280.035 (2)0.035 (3)0.034 (3)0.0047 (18)0.0022 (18)0.014 (2)
C290.047 (2)0.028 (2)0.033 (2)0.0030 (19)0.0057 (19)0.013 (2)
C300.053 (3)0.066 (4)0.079 (4)0.015 (3)0.014 (3)0.053 (3)
C310.081 (4)0.059 (4)0.067 (4)0.028 (3)0.018 (3)0.040 (3)
C320.097 (4)0.042 (3)0.073 (4)−0.003 (3)−0.005 (3)0.035 (3)
C330.077 (4)0.058 (4)0.112 (5)−0.030 (3)−0.017 (3)0.048 (4)
C340.054 (3)0.051 (3)0.077 (4)−0.006 (2)−0.014 (3)0.036 (3)
C350.039 (2)0.039 (3)0.032 (2)−0.0059 (19)−0.0058 (18)0.018 (2)
C360.067 (3)0.046 (3)0.028 (3)−0.010 (2)−0.008 (2)0.010 (2)
C370.070 (3)0.032 (3)0.029 (3)0.001 (2)0.011 (2)0.002 (2)
C380.039 (2)0.036 (3)0.034 (3)−0.0002 (19)0.0048 (18)0.016 (2)
C390.025 (2)0.058 (3)0.048 (3)0.000 (2)0.0054 (19)0.027 (3)
C400.030 (2)0.054 (3)0.045 (3)0.013 (2)0.0120 (19)0.028 (2)
C410.036 (2)0.030 (2)0.028 (2)−0.0052 (17)0.0003 (17)0.0122 (19)
C420.051 (2)0.028 (2)0.041 (3)−0.0063 (19)−0.004 (2)0.022 (2)
C430.045 (2)0.027 (2)0.043 (3)0.0004 (18)−0.006 (2)0.018 (2)
C440.0307 (19)0.020 (2)0.028 (2)−0.0006 (16)0.0045 (16)0.0065 (18)
C450.032 (2)0.051 (3)0.033 (2)−0.0027 (19)0.0017 (18)0.015 (2)
C460.033 (2)0.064 (3)0.041 (3)−0.008 (2)0.0066 (19)0.013 (3)
C470.047 (3)0.040 (3)0.046 (3)−0.005 (2)0.018 (2)0.016 (2)
C480.050 (3)0.045 (3)0.040 (3)0.007 (2)0.010 (2)0.027 (2)
C490.034 (2)0.037 (3)0.040 (3)0.0056 (18)0.0035 (18)0.020 (2)
C500.0230 (18)0.037 (2)0.028 (2)−0.0030 (17)−0.0002 (16)0.016 (2)
C510.033 (2)0.030 (2)0.032 (2)0.0012 (17)−0.0052 (17)0.0125 (19)
C520.035 (2)0.043 (3)0.044 (3)0.012 (2)−0.0019 (19)0.019 (2)
C530.030 (2)0.061 (3)0.046 (3)−0.001 (2)−0.0085 (19)0.028 (3)
C540.047 (3)0.051 (3)0.043 (3)−0.003 (2)−0.016 (2)0.011 (2)
C550.037 (2)0.034 (3)0.039 (3)0.0001 (19)−0.0072 (19)0.008 (2)
C560.034 (2)0.023 (2)0.023 (2)−0.0001 (16)−0.0029 (16)0.0076 (18)
C570.055 (3)0.034 (3)0.052 (3)0.010 (2)0.022 (2)0.021 (2)
C580.079 (3)0.035 (3)0.068 (4)0.019 (3)0.027 (3)0.024 (3)
C590.067 (3)0.023 (2)0.049 (3)0.002 (2)−0.004 (2)0.011 (2)
C600.046 (3)0.038 (3)0.080 (4)−0.009 (2)0.002 (2)0.030 (3)
C610.033 (2)0.029 (3)0.069 (3)−0.0016 (18)0.004 (2)0.015 (2)
C620.032 (2)0.032 (2)0.031 (2)0.0018 (17)−0.0019 (17)0.013 (2)
C630.037 (2)0.033 (2)0.036 (3)−0.0023 (18)−0.0058 (18)0.017 (2)
C640.062 (3)0.042 (3)0.055 (3)0.013 (2)0.014 (2)0.025 (3)
C650.074 (3)0.041 (3)0.071 (4)0.020 (3)0.014 (3)0.023 (3)
C660.073 (3)0.036 (3)0.051 (3)0.009 (2)−0.001 (2)0.022 (3)
C670.066 (3)0.040 (3)0.041 (3)−0.007 (2)−0.001 (2)0.025 (2)
C680.052 (3)0.040 (3)0.041 (3)0.000 (2)0.001 (2)0.019 (2)
N10.0373 (17)0.030 (2)0.0233 (19)0.0038 (15)−0.0015 (14)0.0109 (16)
N20.0454 (19)0.030 (2)0.029 (2)0.0013 (16)−0.0012 (15)0.0106 (17)
N30.0379 (18)0.028 (2)0.0283 (19)0.0074 (15)0.0050 (14)0.0109 (16)
N40.048 (2)0.028 (2)0.035 (2)0.0013 (16)0.0074 (16)0.0126 (17)
N50.0274 (16)0.035 (2)0.0277 (19)−0.0018 (14)−0.0032 (13)0.0125 (16)
N60.0351 (18)0.039 (2)0.033 (2)−0.0065 (16)−0.0018 (15)0.0128 (18)
N70.0258 (16)0.032 (2)0.0283 (19)0.0035 (14)−0.0006 (13)0.0117 (17)
N80.0350 (18)0.052 (2)0.033 (2)0.0108 (17)0.0060 (15)0.0187 (19)
N90.0322 (18)0.041 (2)0.035 (2)0.0069 (16)−0.0022 (16)0.0016 (19)
N100.043 (2)0.078 (3)0.062 (3)−0.011 (2)0.006 (2)0.026 (3)
N110.0330 (17)0.032 (2)0.0250 (19)−0.0014 (14)−0.0004 (14)0.0126 (16)
N120.0441 (19)0.0240 (19)0.029 (2)0.0041 (15)0.0069 (15)0.0081 (16)
N130.0297 (16)0.032 (2)0.0269 (19)0.0013 (14)0.0017 (13)0.0162 (16)
N140.0329 (17)0.0288 (19)0.0320 (19)0.0071 (14)0.0062 (14)0.0142 (16)
N150.0336 (16)0.0242 (18)0.0240 (18)−0.0008 (14)−0.0011 (13)0.0094 (15)
N160.0345 (17)0.0252 (19)0.035 (2)0.0040 (14)0.0007 (14)0.0132 (16)
N170.0294 (16)0.031 (2)0.0283 (19)0.0000 (14)0.0002 (14)0.0123 (16)
N180.0305 (17)0.040 (2)0.041 (2)0.0000 (15)0.0005 (15)0.0198 (18)
N190.0298 (17)0.042 (2)0.039 (2)−0.0004 (16)0.0060 (15)0.0128 (19)
N200.040 (2)0.087 (3)0.101 (4)0.022 (2)0.004 (2)0.059 (3)
P10.0258 (5)0.0255 (6)0.0269 (6)0.0018 (4)0.0011 (4)0.0124 (5)
P20.0241 (5)0.0239 (6)0.0259 (6)0.0009 (4)0.0003 (4)0.0103 (5)
Ru10.02614 (16)0.02651 (19)0.02497 (19)0.00370 (13)0.00169 (12)0.01262 (15)
Ru20.02437 (15)0.02269 (18)0.02441 (19)0.00007 (12)0.00033 (12)0.01164 (15)

Geometric parameters (Å, °)

B1—N61.539 (5)C38—N131.339 (5)
B1—N21.548 (5)C38—C391.394 (5)
B1—N41.555 (5)C38—H380.9500
B1—H1'1.0000C39—C401.368 (6)
B2—N141.528 (5)C39—H390.9500
B2—N161.542 (5)C40—N141.349 (4)
B2—N121.545 (5)C40—H400.9500
B2—H2'1.0000C41—N151.336 (4)
C1—N11.339 (4)C41—C421.390 (5)
C1—C21.392 (6)C41—H410.9500
C1—H10.9500C42—C431.368 (5)
C2—C31.386 (6)C42—H420.9500
C2—H20.9500C43—N161.344 (4)
C3—N21.345 (5)C43—H430.9500
C3—H30.9500C44—C491.384 (5)
C4—N31.341 (4)C44—C451.404 (5)
C4—C51.379 (6)C44—P21.849 (3)
C4—H40.9500C45—C461.391 (5)
C5—C61.366 (6)C45—H450.9500
C5—H50.9500C46—C471.382 (6)
C6—N41.352 (4)C46—H460.9500
C6—H60.9500C47—C481.360 (6)
C7—N51.338 (4)C47—H470.9500
C7—C81.389 (5)C48—C491.382 (5)
C7—H70.9500C48—H480.9500
C8—C91.364 (6)C49—H490.9500
C8—H80.9500C50—C551.387 (5)
C9—N61.350 (4)C50—C511.396 (5)
C9—H90.9500C50—P21.845 (3)
C10—C151.383 (5)C51—C521.382 (5)
C10—C111.391 (5)C51—H510.9500
C10—P11.840 (3)C52—C531.378 (6)
C11—C121.391 (5)C52—H520.9500
C11—H110.9500C53—C541.378 (5)
C12—C131.372 (6)C53—H530.9500
C12—H120.9500C54—C551.381 (5)
C13—C141.368 (6)C54—H540.9500
C13—H130.9500C55—H550.9500
C14—C151.399 (5)C56—C571.373 (5)
C14—H140.9500C56—C611.381 (5)
C15—H150.9500C56—P21.837 (4)
C16—C171.392 (5)C57—C581.392 (5)
C16—C211.389 (5)C57—H570.9500
C16—P11.842 (3)C58—C591.376 (6)
C17—C181.383 (5)C58—H580.9500
C17—H170.9500C59—C601.376 (5)
C18—C191.378 (5)C59—H590.9500
C18—H180.9500C60—C611.385 (5)
C19—C201.361 (5)C60—H600.9500
C19—H190.9500C61—H610.9500
C20—C211.387 (5)C62—N171.143 (4)
C20—H200.9500C62—C631.438 (5)
C21—H210.9500C63—C681.376 (5)
C22—C231.380 (5)C63—C641.385 (5)
C22—C271.396 (5)C64—C651.376 (5)
C22—P11.848 (4)C64—H640.9500
C23—C241.404 (5)C65—C661.374 (6)
C23—H230.9500C65—H650.9500
C24—C251.345 (6)C66—C671.341 (6)
C24—H240.9500C66—H660.9500
C25—C261.358 (7)C67—C681.398 (5)
C25—H250.9500C67—H670.9500
C26—C271.392 (6)C68—H680.9500
C26—H260.9500N1—N21.355 (4)
C27—H270.9500N3—N41.368 (4)
C28—N71.150 (4)N5—N61.366 (4)
C28—C291.429 (5)N8—N91.172 (4)
C29—C341.374 (5)N9—N101.188 (4)
C29—C301.384 (5)N11—N121.367 (4)
C30—C311.364 (6)N13—N141.373 (4)
C30—H300.9500N15—N161.372 (4)
C31—C321.356 (7)N18—N191.173 (4)
C31—H310.9500N19—N201.172 (4)
C32—C331.353 (7)Ru1—N12.122 (3)
C32—H320.9500Ru1—N32.075 (3)
C33—C341.398 (6)Ru1—N52.086 (3)
C33—H330.9500Ru1—N71.984 (3)
C34—H340.9500Ru1—N82.119 (3)
C35—N111.337 (4)Ru1—P12.3068 (11)
C35—C361.383 (5)Ru2—N112.109 (3)
C35—H350.9500Ru2—N132.083 (3)
C36—C371.366 (6)Ru2—N152.077 (3)
C36—H360.9500Ru2—N171.983 (3)
C37—N121.345 (5)Ru2—N182.108 (3)
C37—H370.9500Ru2—P22.3204 (10)
N6—B1—N2107.2 (3)C48—C47—C46119.4 (4)
N6—B1—N4107.9 (3)C48—C47—H47120.3
N2—B1—N4107.3 (3)C46—C47—H47120.3
N6—B1—H1'111.4C47—C48—C49120.8 (4)
N2—B1—H1'111.4C47—C48—H48119.6
N4—B1—H1'111.4C49—C48—H48119.6
N14—B2—N16108.1 (3)C48—C49—C44121.3 (4)
N14—B2—N12107.9 (3)C48—C49—H49119.3
N16—B2—N12108.1 (3)C44—C49—H49119.3
N14—B2—H2'110.9C55—C50—C51118.4 (3)
N16—B2—H2'110.9C55—C50—P2122.5 (3)
N12—B2—H2'110.9C51—C50—P2119.0 (3)
N1—C1—C2110.0 (4)C52—C51—C50120.1 (4)
N1—C1—H1125.0C52—C51—H51120.0
C2—C1—H1125.0C50—C51—H51120.0
C3—C2—C1104.7 (4)C51—C52—C53121.0 (4)
C3—C2—H2127.7C51—C52—H52119.5
C1—C2—H2127.7C53—C52—H52119.5
N2—C3—C2108.6 (4)C54—C53—C52119.2 (4)
N2—C3—H3125.7C54—C53—H53120.4
C2—C3—H3125.7C52—C53—H53120.4
N3—C4—C5110.0 (4)C53—C54—C55120.4 (4)
N3—C4—H4125.0C53—C54—H54119.8
C5—C4—H4125.0C55—C54—H54119.8
C6—C5—C4106.2 (4)C54—C55—C50120.9 (4)
C6—C5—H5126.9C54—C55—H55119.5
C4—C5—H5126.9C50—C55—H55119.5
N4—C6—C5108.0 (4)C57—C56—C61117.0 (3)
N4—C6—H6126.0C57—C56—P2124.0 (3)
C5—C6—H6126.0C61—C56—P2119.0 (3)
N5—C7—C8110.7 (4)C56—C57—C58121.6 (4)
N5—C7—H7124.7C56—C57—H57119.2
C8—C7—H7124.7C58—C57—H57119.2
C9—C8—C7105.4 (4)C59—C58—C57120.3 (4)
C9—C8—H8127.3C59—C58—H58119.8
C7—C8—H8127.3C57—C58—H58119.8
N6—C9—C8108.2 (4)C58—C59—C60118.9 (4)
N6—C9—H9125.9C58—C59—H59120.6
C8—C9—H9125.9C60—C59—H59120.6
C15—C10—C11118.7 (3)C59—C60—C61119.8 (4)
C15—C10—P1119.9 (3)C59—C60—H60120.1
C11—C10—P1121.1 (3)C61—C60—H60120.1
C12—C11—C10120.6 (4)C56—C61—C60122.3 (4)
C12—C11—H11119.7C56—C61—H61118.9
C10—C11—H11119.7C60—C61—H61118.9
C13—C12—C11120.1 (4)N17—C62—C63172.8 (4)
C13—C12—H12119.9C68—C63—C64119.9 (4)
C11—C12—H12119.9C68—C63—C62123.1 (4)
C14—C13—C12120.0 (4)C64—C63—C62116.9 (3)
C14—C13—H13120.0C65—C64—C63119.6 (4)
C12—C13—H13120.0C65—C64—H64120.2
C13—C14—C15120.5 (4)C63—C64—H64120.2
C13—C14—H14119.8C64—C65—C66120.3 (4)
C15—C14—H14119.8C64—C65—H65119.8
C10—C15—C14120.1 (4)C66—C65—H65119.8
C10—C15—H15119.9C67—C66—C65120.3 (4)
C14—C15—H15119.9C67—C66—H66119.9
C17—C16—C21117.8 (3)C65—C66—H66119.9
C17—C16—P1119.3 (3)C66—C67—C68120.8 (4)
C21—C16—P1122.8 (3)C66—C67—H67119.6
C18—C17—C16120.9 (4)C68—C67—H67119.6
C18—C17—H17119.6C63—C68—C67119.0 (4)
C16—C17—H17119.6C63—C68—H68120.5
C19—C18—C17120.3 (4)C67—C68—H68120.5
C19—C18—H18119.8C1—N1—N2107.3 (3)
C17—C18—H18119.8C1—N1—Ru1134.2 (3)
C20—C19—C18119.5 (3)N2—N1—Ru1118.6 (2)
C20—C19—H19120.2C3—N2—N1109.4 (3)
C18—C19—H19120.2C3—N2—B1130.5 (4)
C19—C20—C21120.7 (4)N1—N2—B1120.1 (3)
C19—C20—H20119.7C4—N3—N4106.4 (3)
C21—C20—H20119.7C4—N3—Ru1135.1 (3)
C20—C21—C16120.8 (3)N4—N3—Ru1118.5 (2)
C20—C21—H21119.6C6—N4—N3109.4 (3)
C16—C21—H21119.6C6—N4—B1129.8 (4)
C23—C22—C27117.5 (4)N3—N4—B1120.6 (3)
C23—C22—P1124.0 (3)C7—N5—N6105.8 (3)
C27—C22—P1118.5 (3)C7—N5—Ru1136.0 (3)
C22—C23—C24120.6 (4)N6—N5—Ru1118.2 (2)
C22—C23—H23119.7C9—N6—N5109.9 (3)
C24—C23—H23119.7C9—N6—B1128.8 (4)
C25—C24—C23120.7 (5)N5—N6—B1121.0 (3)
C25—C24—H24119.6C28—N7—Ru1176.9 (3)
C23—C24—H24119.6N9—N8—Ru1123.8 (3)
C24—C25—C26119.9 (5)N8—N9—N10176.8 (4)
C24—C25—H25120.1C35—N11—N12106.1 (3)
C26—C25—H25120.1C35—N11—Ru2134.2 (3)
C25—C26—C27120.7 (4)N12—N11—Ru2119.7 (2)
C25—C26—H26119.6C37—N12—N11109.7 (3)
C27—C26—H26119.6C37—N12—B2131.9 (3)
C26—C27—C22120.5 (5)N11—N12—B2118.4 (3)
C26—C27—H27119.8C38—N13—N14105.5 (3)
C22—C27—H27119.8C38—N13—Ru2136.3 (3)
N7—C28—C29179.0 (4)N14—N13—Ru2118.0 (2)
C34—C29—C30119.1 (4)C40—N14—N13109.4 (3)
C34—C29—C28121.1 (4)C40—N14—B2129.6 (3)
C30—C29—C28119.7 (4)N13—N14—B2120.9 (3)
C31—C30—C29120.8 (4)C41—N15—N16106.4 (3)
C31—C30—H30119.6C41—N15—Ru2135.1 (3)
C29—C30—H30119.6N16—N15—Ru2118.5 (2)
C32—C31—C30120.1 (5)C43—N16—N15109.0 (3)
C32—C31—H31119.9C43—N16—B2130.8 (3)
C30—C31—H31119.9N15—N16—B2120.2 (3)
C33—C32—C31120.4 (5)C62—N17—Ru2175.3 (3)
C33—C32—H32119.8N19—N18—Ru2125.9 (3)
C31—C32—H32119.8N20—N19—N18175.7 (4)
C32—C33—C34120.6 (5)C10—P1—C16101.27 (15)
C32—C33—H33119.7C10—P1—C22101.87 (16)
C34—C33—H33119.7C16—P1—C22102.37 (17)
C29—C34—C33119.0 (4)C10—P1—Ru1116.14 (13)
C29—C34—H34120.5C16—P1—Ru1116.39 (11)
C33—C34—H34120.5C22—P1—Ru1116.42 (12)
N11—C35—C36110.3 (4)C56—P2—C50102.06 (17)
N11—C35—H35124.9C56—P2—C44102.77 (16)
C36—C35—H35124.9C50—P2—C44100.64 (16)
C37—C36—C35105.7 (4)C56—P2—Ru2116.66 (12)
C37—C36—H36127.2C50—P2—Ru2115.27 (12)
C35—C36—H36127.2C44—P2—Ru2117.02 (13)
N12—C37—C36108.2 (4)N7—Ru1—N3174.90 (12)
N12—C37—H37125.9N7—Ru1—N591.69 (11)
C36—C37—H37125.9N3—Ru1—N589.56 (12)
N13—C38—C39111.4 (4)N7—Ru1—N889.40 (12)
N13—C38—H38124.3N3—Ru1—N888.78 (12)
C39—C38—H38124.3N5—Ru1—N8173.12 (13)
C40—C39—C38104.2 (3)N7—Ru1—N190.41 (12)
C40—C39—H39127.9N3—Ru1—N184.76 (12)
C38—C39—H39127.9N5—Ru1—N185.30 (12)
N14—C40—C39109.4 (3)N8—Ru1—N187.90 (12)
N14—C40—H40125.3N7—Ru1—P192.34 (9)
C39—C40—H40125.3N3—Ru1—P192.52 (9)
N15—C41—C42110.5 (3)N5—Ru1—P193.70 (9)
N15—C41—H41124.8N8—Ru1—P193.05 (10)
C42—C41—H41124.8N1—Ru1—P1177.11 (9)
C43—C42—C41104.9 (3)N17—Ru2—N15175.44 (12)
C43—C42—H42127.5N17—Ru2—N1391.90 (11)
C41—C42—H42127.5N15—Ru2—N1388.56 (11)
N16—C43—C42109.2 (3)N17—Ru2—N1889.20 (12)
N16—C43—H43125.4N15—Ru2—N1889.72 (11)
C42—C43—H43125.4N13—Ru2—N18171.90 (13)
C49—C44—C45117.8 (3)N17—Ru2—N1190.68 (12)
C49—C44—P2122.8 (3)N15—Ru2—N1184.83 (11)
C45—C44—P2119.3 (3)N13—Ru2—N1185.80 (11)
C46—C45—C44120.1 (4)N18—Ru2—N1186.16 (12)
C46—C45—H45119.9N17—Ru2—P292.09 (9)
C44—C45—H45119.9N15—Ru2—P292.39 (9)
C47—C46—C45120.5 (4)N13—Ru2—P294.69 (9)
C47—C46—H46119.7N18—Ru2—P293.29 (9)
C45—C46—H46119.7N11—Ru2—P2177.17 (8)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2311).

References

  • Dori, Z. & Ziolo, R. F. (1973). Chem. Rev 73, 247–254.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Huynh, M. H. V., Meyer, T. J., Labouriau, A., Morris, D. E. & White, P. S. (2003). J. Am. Chem. Soc 125, 2828–2829. [PubMed]
  • Krivopalov, V. P. & Shkurko, O. P. (2005). Russ. Chem. Rev.74, 339–379.
  • Meyer, K., Bendix, J., Metzler-Nolte, N., Weyhermüller, T. & Wieghardt, K. (1998). J. Am. Chem. Soc 120, 7260–7270.
  • Nonius (1998). COLLECT Nonius BV, Delft, The Netherlands.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  • Padwa, A. (1976). Angew. Chem. Int. Ed. Engl.15, 123–136.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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