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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m325–m326.
Published online 2010 February 24. doi:  10.1107/S1600536810006252
PMCID: PMC2983605

Hexakis(acetonitrile-κN)ruthenium(II) bis­(hexa­bromo­carbadodeca­borate) aceto­nitrile solvate

Abstract

The title compound, [Ru(NCCH3)6](CH6B11Br6)2·CH3CN, consists of the ’naked’ ruthenium(II) cation surrounded by six acetonitrile mol­ecules, each coordinated via the nitro­gen atoms in a linear or nearly-linear fashion in a typical octa­hedral over-all arrangement. The cation is balanced by the two hexa-bromo­carborane cage anionic fragments [CB11H6Br6]. Weak C—H(...)Br and B—H(...)Br inter­actions link neighboring anions.

Related literature

For related literature pertaining to ruthenium and ruthenium derivative structures, see: Bergman & Chang (1987 [triangle]); Burns & Hubbard (1994 [triangle]); Stasko et al. (2002 [triangle]); Brookhart et al. (1992 [triangle]). For related ruthenium structures, see: Pearsal et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m325-scheme1.jpg

Experimental

Crystal data

  • [Ru(C2H3N)6](CH6B11Br6)2·C2H3N
  • M r = 1621.30
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m325-efi1.jpg
  • a = 21.332 (2) Å
  • b = 11.7577 (10) Å
  • c = 20.2620 (17) Å
  • V = 5082.1 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 9.77 mm−1
  • T = 173 K
  • 0.20 × 0.15 × 0.10 mm

Data collection

  • Bruker CCD-1000 area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2007 [triangle]) T min = 0.245, T max = 0.442
  • 36328 measured reflections
  • 13481 independent reflections
  • 10985 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.062
  • S = 0.97
  • 13481 reflections
  • 531 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.83 e Å−3
  • Δρmin = −0.73 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 6319 Friedel pairs
  • Flack parameter: 0.000 (5)

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006252/ez2197sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006252/ez2197Isup2.hkl

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

Acknowledgments

We thank the National Science Foundation for financial support. Support of this research via the PRF 44692.01-GB award by the American Chemical Society and the Cottrell College Award CC6755 from Research Corporation is gratefully acknowledged. We are grateful to Dr Ilia A. Guzei (University of Wisconsin, Madison) for his help in the preparation of this submission.

supplementary crystallographic information

Comment

Electrophilic complexes with the [Cp*Ru(NO)] core are reactive towards small molecular nucleophiles. In the presence of labile neutral ligands or weakly coordinating anions, such as trifluoromethanesulfonate, these complexes exhibit pro-catalytic reactivity with unsaturated hydrocarbons and alcohols (Burns and Hubbard, 1994; Pearsal et al., 2007). The present study's goal is introduction of the non-coordinating carborane cage anions of the [CB11H12] family in order to increase the reactivity of the ruthenium catalytic center (Stasko et al., 2002). The synthetic route to the desired complexes includes protonation of the dialkyl starting material with the solvated proton salt of the weakly-coordinating anion (similar to Brookhart, et al., 1992). This process eventually results in stripping all the ligands off the ruthenium center to give the title compound comprised of the 'naked' hexa-acetonitrile ruthenium cationic fragment balanced by two hexa-bromo-carborane anionic fragments. The catalytic activity of this complex is currently under investigation.

Experimental

The compound was obtained by a prolonged exposure of the Cp*Ru(NO)(CH3)2 complex to an excess of carborane-based protonating agent [(C2H5OC2H5)2 H]+ [CB11H6Br6]- in acetonitrile.

All synthetic procedures were carried out in inert atmosphere and in anhydrous solvents. The protonating agent [(C2H5OC2H5)2 H]+ [CB11H6Br6]- and starting ruthenium complex Cp*Ru(NO)(CH3)2 were synthesized according to the reported procedures (Stasko et al., 2002; Bergman & Chang,1987).

20 mg (0.065 mmol) of Cp*Ru(NO)(CH3)2 were dissolved in 10 ml of CH3CN and the solution was added to 200 mg of solid [(C2H5OC2H5)2 H]+ [CB11H6Br6]- (0.265 mmol). Vigorous evolution of a gas (methane) was observed. The color of the solution gradually changed from dark red to dark purple-red. Initial product of the reaction, [Cp*Ru(NO)(CH3)(NCCH3)] [CB11H6Br6], formed via a mono-protonation process and loss of one methane molecule from the starting material, was observed spectroscopically (by 1H NMR) in the aliquot of the reaction mixture taken after 4 hrs. The red crystals of the [Ru(NCCH3)6]] [CB11H6Br6]2 were grown from the reaction mixture in acetonitrile at ambient temperature under nitrogen by slow evaporation over a period of 3 weeks.

Refinement

All H-atoms were placed in idealized locations and refined as riding with appropriate thermal displacement coefficients Uiso(H) = 1.2 or 1.5 times Ueq(bearing atom).

All H-atoms were placed in idealized locations with C—H distances of 0.981 Å for methyl carbons, and B—H and other C—H distances of 1.212 Å and refined as riding with thermal displacement coefficients Uiso(H) set to 1.5 times Ueq(bearing C atom) for the methyl atoms and 1.2 times Ueq(bearing atom) otherwise.

Figures

Fig. 1.
Molecular structure of (I)with atom numbering scheme. The thermal ellipsoids are shown at 50% probability level.

Crystal data

[Ru(C2H3N)6](CH6B11Br6)2·C2H3NF(000) = 3008
Mr = 1621.30Dx = 2.119 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 999 reflections
a = 21.332 (2) Åθ = 1.9–29.3°
b = 11.7577 (10) ŵ = 9.77 mm1
c = 20.2620 (17) ÅT = 173 K
V = 5082.1 (8) Å3Block, red
Z = 40.20 × 0.15 × 0.10 mm

Data collection

Bruker CCD-1000 area-detector diffractometer13481 independent reflections
Radiation source: fine-focus sealed tube10985 reflections with I > 2σ(I)
graphiteRint = 0.042
0.30° ω and 0.4 ° [var phi] scansθmax = 29.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −29→28
Tmin = 0.245, Tmax = 0.442k = −16→15
36328 measured reflectionsl = −27→27

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.062w = 1/[σ2(Fo2) + (0.002P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
13481 reflectionsΔρmax = 0.83 e Å3
531 parametersΔρmin = −0.72 e Å3
1 restraintAbsolute structure: Flack (1983), 6319 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.000 (5)

Special details

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)

xyzUiso*/Ueq
Ru10.399141 (18)0.77943 (3)0.705666 (18)0.02190 (8)
N10.3418 (2)0.8915 (3)0.75141 (19)0.0252 (9)
N20.3486 (2)0.6518 (3)0.74612 (18)0.0232 (9)
N30.4578 (2)0.7767 (3)0.7844 (2)0.0289 (9)
N40.4530 (2)0.6611 (3)0.66043 (19)0.0245 (9)
N50.4493 (2)0.9056 (3)0.66337 (19)0.0261 (9)
N60.34097 (19)0.7832 (3)0.62615 (19)0.0229 (8)
C10.3052 (3)0.9451 (4)0.7782 (2)0.0264 (11)
C20.2595 (3)1.0150 (4)0.8113 (3)0.0371 (13)
H2C0.28021.06030.84550.056*
H2B0.22760.96630.83170.056*
H2A0.23951.06590.77930.056*
C30.3216 (2)0.5780 (4)0.7671 (2)0.0271 (11)
C40.2864 (3)0.4804 (4)0.7934 (3)0.0355 (13)
H4C0.31270.43900.82500.053*
H4A0.27470.42970.75700.053*
H4B0.24850.50760.81560.053*
C50.4903 (2)0.7721 (4)0.8281 (2)0.0256 (10)
C60.5326 (3)0.7672 (4)0.8846 (2)0.0354 (12)
H6B0.57560.78210.86990.053*
H6A0.53040.69150.90470.053*
H6C0.52020.82460.91710.053*
C70.4787 (2)0.5888 (4)0.6358 (2)0.0261 (10)
C80.5105 (3)0.4935 (4)0.6042 (3)0.0370 (13)
H8C0.53550.45240.63700.055*
H8B0.53820.52220.56930.055*
H8A0.47940.44200.58490.055*
C90.4757 (2)0.9733 (4)0.6354 (3)0.0299 (11)
C100.5104 (3)1.0596 (4)0.5984 (3)0.0435 (15)
H10B0.48371.12640.59170.065*
H10A0.52291.02850.55550.065*
H10C0.54791.08170.62330.065*
C110.3105 (2)0.7833 (4)0.5804 (2)0.0256 (11)
C120.2710 (3)0.7818 (4)0.5225 (2)0.0324 (12)
H12A0.25390.70520.51630.049*
H12B0.29580.80320.48380.049*
H12C0.23650.83600.52820.049*
Br10.09098 (2)0.22557 (4)0.51235 (3)0.02750 (11)
Br20.17891 (3)0.50024 (3)0.48909 (2)0.02850 (11)
Br30.32771 (2)0.48584 (3)0.59669 (2)0.02548 (10)
Br40.33173 (3)0.19992 (4)0.68133 (3)0.03209 (12)
Br50.18567 (3)0.03424 (4)0.63167 (3)0.03231 (12)
Br60.17687 (2)0.35779 (4)0.65791 (2)0.02565 (10)
C0AA0.2963 (2)0.1822 (4)0.4613 (2)0.0220 (10)
H0A0.32210.14380.41860.026*
B10.1813 (2)0.2282 (4)0.5161 (3)0.0195 (10)
B20.2239 (2)0.3581 (4)0.5052 (2)0.0191 (10)
B30.2923 (2)0.3521 (4)0.5546 (2)0.0180 (10)
B40.2940 (2)0.2181 (4)0.5941 (3)0.0197 (10)
B50.2248 (3)0.1416 (4)0.5710 (2)0.0188 (10)
B60.2212 (2)0.2911 (4)0.5838 (2)0.0147 (10)
B70.2284 (3)0.2502 (4)0.4441 (3)0.0229 (12)
H70.20770.25980.39370.028*
B80.2965 (3)0.3270 (4)0.4675 (3)0.0233 (11)
H80.32040.38690.43270.028*
B90.3402 (3)0.2401 (4)0.5234 (3)0.0225 (11)
H90.39260.24330.52500.027*
B100.2980 (3)0.1107 (4)0.5337 (3)0.0232 (11)
H100.32320.02830.54220.028*
B110.2287 (3)0.1170 (4)0.4860 (3)0.0218 (11)
H110.20800.03890.46300.026*
Br70.32987 (2)0.77287 (4)0.33363 (2)0.02870 (11)
Br80.42000 (3)0.93866 (4)0.46079 (3)0.03373 (12)
Br90.56818 (3)0.76830 (4)0.50431 (3)0.03494 (12)
Br100.56984 (2)0.50141 (4)0.39952 (3)0.02875 (11)
Br110.42319 (3)0.49971 (4)0.29036 (3)0.03068 (11)
Br120.41484 (2)0.61228 (4)0.46759 (2)0.02423 (10)
C1AA0.5353 (3)0.8272 (4)0.2853 (2)0.0291 (11)
H1A0.56100.87420.24550.035*
B130.4202 (3)0.7666 (4)0.3357 (3)0.0220 (11)
B140.4631 (3)0.8445 (4)0.3960 (3)0.0246 (12)
B150.5318 (3)0.7669 (4)0.4164 (3)0.0235 (11)
B160.5325 (3)0.6418 (4)0.3670 (2)0.0195 (11)
B170.4641 (3)0.6413 (4)0.3173 (2)0.0212 (11)
B180.4606 (2)0.6923 (4)0.4001 (2)0.0170 (10)
B190.4671 (3)0.8845 (4)0.3124 (3)0.0263 (12)
H190.44580.96540.29370.032*
B200.5362 (3)0.8849 (5)0.3618 (3)0.0286 (13)
H200.56070.96580.37560.034*
B210.5796 (3)0.7595 (4)0.3441 (3)0.0277 (13)
H210.63210.75780.34620.033*
B220.5369 (3)0.6817 (4)0.2831 (3)0.0252 (12)
H220.56150.62880.24520.030*
B230.4681 (3)0.7597 (5)0.2636 (3)0.0277 (13)
H230.44790.75840.21260.033*
N1S0.6665 (3)0.8100 (6)0.7904 (3)0.083 (2)
C1S0.6582 (4)0.8053 (6)0.7357 (4)0.063 (2)
C2S0.6476 (6)0.8005 (6)0.6695 (4)0.126 (5)
H2SC0.67780.84950.64660.189*
H2SB0.60500.82660.66000.189*
H2SA0.65260.72200.65420.189*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ru10.0257 (2)0.01802 (17)0.02196 (19)−0.00100 (15)0.00163 (16)−0.00001 (15)
N10.032 (3)0.0193 (18)0.024 (2)0.0028 (17)0.0022 (19)0.0000 (16)
N20.030 (2)0.0195 (18)0.019 (2)0.0012 (16)0.0004 (17)0.0005 (16)
N30.033 (3)0.0214 (19)0.033 (2)−0.0021 (18)0.002 (2)−0.0021 (18)
N40.030 (2)0.0212 (19)0.022 (2)0.0006 (17)−0.0014 (18)−0.0010 (16)
N50.031 (2)0.0239 (19)0.024 (2)−0.0030 (17)0.0016 (19)−0.0023 (17)
N60.028 (2)0.0170 (18)0.023 (2)0.0010 (15)0.0021 (18)0.0010 (16)
C10.036 (3)0.021 (2)0.021 (3)0.002 (2)0.004 (2)0.0048 (19)
C20.039 (4)0.046 (3)0.026 (3)0.010 (3)0.005 (2)0.001 (2)
C30.028 (3)0.031 (3)0.022 (3)0.002 (2)−0.006 (2)−0.004 (2)
C40.044 (4)0.029 (3)0.034 (3)−0.015 (2)−0.006 (3)0.005 (2)
C50.026 (3)0.024 (2)0.026 (3)−0.005 (2)0.004 (2)−0.002 (2)
C60.033 (3)0.044 (3)0.029 (3)−0.011 (2)−0.005 (2)−0.004 (2)
C70.026 (3)0.028 (2)0.024 (3)−0.007 (2)−0.006 (2)0.003 (2)
C80.036 (3)0.037 (3)0.037 (3)0.014 (2)0.003 (3)−0.004 (2)
C90.030 (3)0.028 (2)0.031 (3)−0.008 (2)−0.002 (2)−0.007 (2)
C100.057 (4)0.042 (3)0.032 (3)−0.023 (3)0.008 (3)−0.002 (3)
C110.032 (3)0.019 (2)0.026 (3)−0.0016 (19)0.005 (2)0.0027 (19)
C120.037 (3)0.027 (2)0.033 (3)−0.001 (2)−0.008 (2)0.004 (2)
Br10.0190 (2)0.0286 (2)0.0349 (3)−0.00053 (19)−0.0065 (2)−0.0091 (2)
Br20.0357 (3)0.0201 (2)0.0297 (3)0.00673 (19)−0.0053 (2)0.00434 (19)
Br30.0292 (3)0.0224 (2)0.0248 (2)−0.01019 (18)−0.0001 (2)−0.00055 (19)
Br40.0332 (3)0.0362 (3)0.0269 (3)−0.0033 (2)−0.0145 (2)0.0097 (2)
Br50.0342 (3)0.0264 (2)0.0362 (3)−0.0099 (2)−0.0006 (2)0.0116 (2)
Br60.0253 (3)0.0345 (2)0.0171 (2)−0.0024 (2)0.0058 (2)−0.00666 (19)
C0AA0.026 (3)0.024 (2)0.017 (2)0.0020 (19)0.002 (2)−0.0049 (18)
B10.017 (2)0.018 (2)0.023 (3)0.001 (2)−0.002 (2)−0.005 (2)
B20.018 (3)0.024 (2)0.015 (3)−0.0007 (19)0.000 (2)0.001 (2)
B30.017 (3)0.019 (2)0.019 (3)−0.0014 (19)0.002 (2)0.0022 (19)
B40.017 (2)0.017 (2)0.025 (3)−0.0018 (19)−0.002 (2)0.001 (2)
B50.019 (3)0.018 (2)0.020 (3)0.001 (2)−0.003 (2)0.0040 (19)
B60.019 (3)0.015 (2)0.010 (2)−0.0009 (18)0.0012 (18)0.0004 (18)
B70.025 (3)0.026 (3)0.018 (3)0.001 (2)−0.003 (2)−0.0032 (19)
B80.025 (3)0.026 (3)0.019 (3)0.004 (2)0.000 (2)0.000 (2)
B90.023 (3)0.024 (3)0.021 (3)0.004 (2)−0.002 (2)0.000 (2)
B100.023 (3)0.020 (2)0.027 (3)0.003 (2)0.001 (2)0.000 (2)
B110.021 (3)0.020 (2)0.025 (3)0.001 (2)0.000 (2)−0.006 (2)
Br70.0210 (3)0.0375 (3)0.0276 (3)0.0067 (2)−0.0004 (2)0.0066 (2)
Br80.0399 (3)0.0236 (2)0.0376 (3)0.0011 (2)0.0123 (2)−0.0059 (2)
Br90.0384 (3)0.0375 (3)0.0290 (3)−0.0131 (2)−0.0098 (2)0.0016 (2)
Br100.0275 (3)0.0234 (2)0.0353 (3)0.0061 (2)−0.0020 (2)0.00958 (19)
Br110.0340 (3)0.0301 (2)0.0279 (3)0.0008 (2)−0.0059 (2)−0.0072 (2)
Br120.0267 (3)0.0265 (2)0.0195 (2)−0.00456 (18)0.0039 (2)0.00747 (18)
C1AA0.030 (3)0.029 (2)0.028 (3)0.006 (2)0.008 (2)0.014 (2)
B130.024 (3)0.030 (3)0.012 (2)0.003 (2)0.004 (2)0.004 (2)
B140.030 (3)0.017 (2)0.027 (3)0.002 (2)0.007 (2)−0.002 (2)
B150.026 (3)0.022 (2)0.023 (3)−0.003 (2)−0.001 (2)0.007 (2)
B160.022 (3)0.023 (3)0.013 (2)0.004 (2)0.002 (2)0.011 (2)
B170.021 (3)0.025 (3)0.017 (3)0.005 (2)0.000 (2)0.003 (2)
B180.017 (3)0.021 (2)0.013 (2)−0.0002 (19)0.002 (2)0.0072 (19)
B190.024 (3)0.024 (3)0.032 (3)0.005 (2)0.007 (2)0.017 (2)
B200.026 (3)0.024 (3)0.036 (3)−0.006 (2)0.009 (3)0.002 (2)
B210.019 (3)0.030 (3)0.035 (3)−0.002 (2)0.007 (2)0.010 (2)
B220.029 (3)0.029 (3)0.018 (3)0.006 (2)0.007 (2)0.008 (2)
B230.025 (3)0.036 (3)0.022 (3)0.008 (2)0.007 (2)0.013 (2)
N1S0.069 (5)0.136 (6)0.044 (4)−0.032 (4)−0.001 (3)0.016 (4)
C1S0.067 (5)0.067 (5)0.053 (5)0.000 (4)0.000 (4)0.016 (4)
C2S0.236 (15)0.059 (5)0.083 (7)0.032 (7)−0.043 (8)−0.017 (5)

Geometric parameters (Å, °)

Ru1—N52.020 (4)B4—B61.785 (7)
Ru1—N22.021 (4)B4—B51.790 (7)
Ru1—N12.022 (4)B5—B111.750 (7)
Ru1—N42.024 (4)B5—B101.773 (7)
Ru1—N32.028 (4)B5—B61.777 (6)
Ru1—N62.034 (4)B7—B81.776 (8)
N1—C11.142 (6)B7—B111.780 (7)
N2—C31.126 (6)B7—H71.1200
N3—C51.127 (6)B8—B91.786 (7)
N4—C71.127 (6)B8—H81.1200
N5—C91.126 (6)B9—B101.781 (7)
N6—C111.132 (6)B9—H91.1200
C1—C21.441 (7)B10—B111.768 (8)
C2—H2C0.9800B10—H101.1200
C2—H2B0.9800B11—H111.1200
C2—H2A0.9800Br7—B131.928 (6)
C3—C41.470 (7)Br8—B141.948 (5)
C4—H4C0.9800Br9—B151.944 (5)
C4—H4A0.9800Br10—B161.947 (5)
C4—H4B0.9800Br11—B171.958 (5)
C5—C61.457 (7)Br12—B181.926 (5)
C6—H6B0.9800C1AA—B201.694 (7)
C6—H6A0.9800C1AA—B191.695 (7)
C6—H6C0.9800C1AA—B231.696 (8)
C7—C81.459 (7)C1AA—B221.712 (7)
C8—H8C0.9800C1AA—B211.717 (7)
C8—H8B0.9800C1AA—H1A1.1200
C8—H8A0.9800B13—B191.774 (7)
C9—C101.463 (7)B13—B141.780 (8)
C10—H10B0.9800B13—B171.785 (7)
C10—H10A0.9800B13—B231.787 (8)
C10—H10C0.9800B13—B181.791 (7)
C11—C121.445 (7)B14—B191.759 (7)
C12—H12A0.9800B14—B201.773 (8)
C12—H12B0.9800B14—B151.776 (8)
C12—H12C0.9800B14—B181.792 (6)
Br1—B11.929 (5)B15—B201.776 (7)
Br2—B21.955 (5)B15—B161.778 (7)
Br3—B31.943 (5)B15—B181.784 (7)
Br4—B41.954 (5)B15—B211.786 (8)
Br5—B51.950 (5)B16—B221.767 (7)
Br6—B61.940 (5)B16—B211.772 (7)
C0AA—B71.690 (7)B16—B171.773 (7)
C0AA—B101.693 (7)B16—B181.776 (7)
C0AA—B81.707 (7)B17—B221.765 (8)
C0AA—B111.707 (7)B17—B231.770 (7)
C0AA—B91.710 (7)B17—B181.782 (7)
C0AA—H0A1.1200B19—B231.770 (8)
B1—B111.761 (7)B19—B201.782 (8)
B1—B51.770 (7)B19—H191.1200
B1—B61.776 (7)B20—B211.778 (8)
B1—B71.789 (7)B20—H201.1200
B1—B21.790 (7)B21—B221.788 (8)
B2—B81.765 (7)B21—H211.1200
B2—B31.770 (7)B22—B231.774 (8)
B2—B71.774 (7)B22—H221.1200
B2—B61.779 (7)B23—H231.1200
B3—B41.767 (7)N1S—C1S1.124 (9)
B3—B61.779 (7)C1S—C2S1.361 (10)
B3—B91.782 (7)C2S—H2SC0.9800
B3—B81.790 (7)C2S—H2SB0.9800
B4—B91.759 (7)C2S—H2SA0.9800
B4—B101.760 (7)
N5—Ru1—N2178.82 (15)B4—B10—B11108.0 (4)
N5—Ru1—N192.08 (16)C0AA—B10—B5104.4 (4)
N2—Ru1—N188.58 (15)B4—B10—B560.9 (3)
N5—Ru1—N490.67 (15)B11—B10—B559.2 (3)
N2—Ru1—N488.65 (15)C0AA—B10—B958.9 (3)
N1—Ru1—N4177.05 (16)B4—B10—B959.5 (3)
N5—Ru1—N391.08 (16)B11—B10—B9108.8 (4)
N2—Ru1—N389.88 (16)B5—B10—B9108.6 (4)
N1—Ru1—N391.28 (16)C0AA—B10—H10125.0
N4—Ru1—N389.73 (16)B4—B10—H10122.5
N5—Ru1—N688.36 (15)B11—B10—H10121.4
N2—Ru1—N690.68 (15)B5—B10—H10122.3
N1—Ru1—N688.86 (16)B9—B10—H10121.0
N4—Ru1—N690.16 (15)C0AA—B11—B5104.8 (4)
N3—Ru1—N6179.43 (17)C0AA—B11—B1104.7 (3)
C1—N1—Ru1172.6 (4)B5—B11—B160.6 (3)
C3—N2—Ru1177.4 (4)C0AA—B11—B1058.3 (3)
C5—N3—Ru1178.2 (4)B5—B11—B1060.5 (3)
C7—N4—Ru1173.9 (4)B1—B11—B10108.8 (4)
C9—N5—Ru1174.9 (4)C0AA—B11—B757.9 (3)
C11—N6—Ru1177.2 (4)B5—B11—B7108.8 (3)
N1—C1—C2178.8 (5)B1—B11—B760.7 (3)
C1—C2—H2C109.5B10—B11—B7107.5 (4)
C1—C2—H2B109.5C0AA—B11—H11125.4
H2C—C2—H2B109.5B5—B11—H11121.7
C1—C2—H2A109.5B1—B11—H11121.7
H2C—C2—H2A109.5B10—B11—H11121.5
H2B—C2—H2A109.5B7—B11—H11121.5
N2—C3—C4178.9 (5)B20—C1AA—B1963.5 (3)
C3—C4—H4C109.5B20—C1AA—B23115.8 (4)
C3—C4—H4A109.5B19—C1AA—B2362.9 (3)
H4C—C4—H4A109.5B20—C1AA—B22115.1 (4)
C3—C4—H4B109.5B19—C1AA—B22115.0 (4)
H4C—C4—H4B109.5B23—C1AA—B2262.8 (3)
H4A—C4—H4B109.5B20—C1AA—B2162.8 (3)
N3—C5—C6179.6 (6)B19—C1AA—B21115.5 (4)
C5—C6—H6B109.5B23—C1AA—B21115.4 (4)
C5—C6—H6A109.5B22—C1AA—B2162.8 (3)
H6B—C6—H6A109.5B20—C1AA—H1A117.1
C5—C6—H6C109.5B19—C1AA—H1A117.2
H6B—C6—H6C109.5B23—C1AA—H1A117.2
H6A—C6—H6C109.5B22—C1AA—H1A117.8
N4—C7—C8178.6 (5)B21—C1AA—H1A117.3
C7—C8—H8C109.5B19—B13—B1459.4 (3)
C7—C8—H8B109.5B19—B13—B17107.0 (4)
H8C—C8—H8B109.5B14—B13—B17107.3 (4)
C7—C8—H8A109.5B19—B13—B2359.6 (3)
H8C—C8—H8A109.5B14—B13—B23106.9 (4)
H8B—C8—H8A109.5B17—B13—B2359.4 (3)
N5—C9—C10179.0 (6)B19—B13—B18107.6 (4)
C9—C10—H10B109.5B14—B13—B1860.2 (3)
C9—C10—H10A109.5B17—B13—B1859.8 (3)
H10B—C10—H10A109.5B23—B13—B18107.4 (4)
C9—C10—H10C109.5B19—B13—Br7121.9 (3)
H10B—C10—H10C109.5B14—B13—Br7120.6 (3)
H10A—C10—H10C109.5B17—B13—Br7123.5 (3)
N6—C11—C12179.0 (5)B23—B13—Br7123.8 (4)
C11—C12—H12A109.5B18—B13—Br7121.1 (3)
C11—C12—H12B109.5B19—B14—B2060.6 (3)
H12A—C12—H12B109.5B19—B14—B15108.7 (4)
C11—C12—H12C109.5B20—B14—B1560.1 (3)
H12A—C12—H12C109.5B19—B14—B1360.2 (3)
H12B—C12—H12C109.5B20—B14—B13108.8 (4)
B7—C0AA—B10115.6 (4)B15—B14—B13108.6 (3)
B7—C0AA—B863.0 (3)B19—B14—B18108.2 (4)
B10—C0AA—B8115.5 (3)B20—B14—B18108.1 (4)
B7—C0AA—B1163.2 (3)B15—B14—B1860.0 (3)
B10—C0AA—B1162.7 (3)B13—B14—B1860.2 (3)
B8—C0AA—B11115.4 (4)B19—B14—Br8121.4 (3)
B7—C0AA—B9115.6 (3)B20—B14—Br8121.8 (3)
B10—C0AA—B963.1 (3)B15—B14—Br8121.6 (4)
B8—C0AA—B963.0 (3)B13—B14—Br8120.9 (4)
B11—C0AA—B9115.2 (4)B18—B14—Br8121.5 (3)
B7—C0AA—H0A117.0B14—B15—B2059.9 (3)
B10—C0AA—H0A117.3B14—B15—B16107.6 (4)
B8—C0AA—H0A117.3B20—B15—B16107.2 (4)
B11—C0AA—H0A117.5B14—B15—B1860.5 (3)
B9—C0AA—H0A117.3B20—B15—B18108.3 (4)
B11—B1—B559.4 (3)B16—B15—B1859.8 (3)
B11—B1—B6107.6 (4)B14—B15—B21107.8 (4)
B5—B1—B660.2 (3)B20—B15—B2159.9 (3)
B11—B1—B760.2 (3)B16—B15—B2159.6 (3)
B5—B1—B7107.6 (4)B18—B15—B21108.1 (4)
B6—B1—B7107.5 (3)B14—B15—Br9122.6 (3)
B11—B1—B2107.4 (4)B20—B15—Br9122.8 (3)
B5—B1—B2107.6 (4)B16—B15—Br9121.2 (3)
B6—B1—B259.8 (3)B18—B15—Br9120.9 (3)
B7—B1—B259.4 (3)B21—B15—Br9121.6 (4)
B11—B1—Br1123.2 (3)B22—B16—B2160.7 (3)
B5—B1—Br1122.6 (3)B22—B16—B1759.8 (3)
B6—B1—Br1121.0 (3)B21—B16—B17108.7 (4)
B7—B1—Br1122.1 (3)B22—B16—B18108.6 (4)
B2—B1—Br1121.0 (3)B21—B16—B18109.1 (4)
B8—B2—B360.8 (3)B17—B16—B1860.3 (3)
B8—B2—B760.2 (3)B22—B16—B15108.8 (3)
B3—B2—B7108.7 (4)B21—B16—B1560.4 (3)
B8—B2—B6108.9 (4)B17—B16—B15108.3 (4)
B3—B2—B660.2 (3)B18—B16—B1560.3 (3)
B7—B2—B6108.0 (3)B22—B16—Br10121.9 (3)
B8—B2—B1108.8 (3)B21—B16—Br10121.3 (3)
B3—B2—B1108.3 (3)B17—B16—Br10121.7 (3)
B7—B2—B160.2 (3)B18—B16—Br10120.6 (3)
B6—B2—B159.7 (3)B15—B16—Br10121.0 (3)
B8—B2—Br2122.4 (3)B22—B17—B2360.3 (3)
B3—B2—Br2122.2 (3)B22—B17—B1659.9 (3)
B7—B2—Br2121.5 (3)B23—B17—B16107.9 (4)
B6—B2—Br2120.8 (3)B22—B17—B18108.4 (4)
B1—B2—Br2120.1 (3)B23—B17—B18108.5 (4)
B4—B3—B2108.0 (4)B16—B17—B1859.9 (3)
B4—B3—B660.5 (3)B22—B17—B13108.8 (4)
B2—B3—B660.2 (3)B23—B17—B1360.3 (3)
B4—B3—B959.4 (3)B16—B17—B13108.1 (4)
B2—B3—B9107.6 (4)B18—B17—B1360.3 (3)
B6—B3—B9108.0 (3)B22—B17—Br11120.7 (3)
B4—B3—B8107.4 (3)B23—B17—Br11121.2 (3)
B2—B3—B859.4 (3)B16—B17—Br11121.9 (3)
B6—B3—B8107.8 (4)B18—B17—Br11122.0 (3)
B9—B3—B860.0 (3)B13—B17—Br11121.7 (4)
B4—B3—Br3120.9 (3)B16—B18—B1759.8 (3)
B2—B3—Br3122.5 (3)B16—B18—B1559.9 (3)
B6—B3—Br3120.8 (3)B17—B18—B15107.7 (4)
B9—B3—Br3122.0 (3)B16—B18—B13107.7 (3)
B8—B3—Br3123.1 (3)B17—B18—B1359.9 (3)
B9—B4—B1060.8 (3)B15—B18—B13107.7 (3)
B9—B4—B360.7 (3)B16—B18—B14106.9 (4)
B10—B4—B3109.0 (4)B17—B18—B14106.9 (3)
B9—B4—B6108.8 (3)B15—B18—B1459.6 (3)
B10—B4—B6107.9 (4)B13—B18—B1459.5 (3)
B3—B4—B660.1 (3)B16—B18—Br12122.8 (3)
B9—B4—B5108.9 (4)B17—B18—Br12121.6 (3)
B10—B4—B559.9 (3)B15—B18—Br12122.7 (3)
B3—B4—B5108.2 (4)B13—B18—Br12120.7 (3)
B6—B4—B559.6 (3)B14—B18—Br12122.4 (3)
B9—B4—Br4121.5 (3)C1AA—B19—B14104.4 (4)
B10—B4—Br4122.0 (3)C1AA—B19—B2358.6 (3)
B3—B4—Br4121.1 (3)B14—B19—B23108.5 (4)
B6—B4—Br4121.1 (3)C1AA—B19—B13105.1 (4)
B5—B4—Br4121.4 (3)B14—B19—B1360.5 (3)
B11—B5—B160.0 (3)B23—B19—B1360.6 (3)
B11—B5—B1060.3 (3)C1AA—B19—B2058.2 (3)
B1—B5—B10108.2 (4)B14—B19—B2060.1 (3)
B11—B5—B6108.0 (3)B23—B19—B20107.9 (4)
B1—B5—B660.1 (3)B13—B19—B20108.6 (4)
B10—B5—B6107.7 (4)C1AA—B19—H19125.1
B11—B5—B4107.5 (4)B14—B19—H19122.2
B1—B5—B4107.9 (3)B23—B19—H19121.3
B10—B5—B459.2 (3)B13—B19—H19121.7
B6—B5—B460.1 (3)B20—B19—H19121.5
B11—B5—Br5122.3 (3)C1AA—B20—B14103.9 (4)
B1—B5—Br5123.0 (3)C1AA—B20—B15104.8 (4)
B10—B5—Br5120.8 (3)B14—B20—B1560.1 (3)
B6—B5—Br5122.0 (3)C1AA—B20—B2159.2 (3)
B4—B5—Br5120.9 (3)B14—B20—B21108.4 (4)
B1—B6—B559.8 (3)B15—B20—B2160.4 (3)
B1—B6—B260.5 (3)C1AA—B20—B1958.3 (3)
B5—B6—B2107.8 (3)B14—B20—B1959.3 (3)
B1—B6—B3108.6 (3)B15—B20—B19107.6 (4)
B5—B6—B3108.2 (3)B21—B20—B19108.3 (4)
B2—B6—B359.7 (3)C1AA—B20—H20125.0
B1—B6—B4107.8 (3)B14—B20—H20122.8
B5—B6—B460.3 (3)B15—B20—H20122.3
B2—B6—B4106.8 (3)B21—B20—H20120.8
B3—B6—B459.4 (3)B19—B20—H20121.8
B1—B6—Br6122.2 (3)C1AA—B21—B16103.4 (4)
B5—B6—Br6122.3 (3)C1AA—B21—B2057.9 (3)
B2—B6—Br6122.0 (3)B16—B21—B20107.4 (4)
B3—B6—Br6120.7 (3)C1AA—B21—B15103.4 (4)
B4—B6—Br6121.9 (3)B16—B21—B1560.0 (3)
C0AA—B7—B2104.0 (4)B20—B21—B1559.8 (3)
C0AA—B7—B859.0 (3)C1AA—B21—B2258.4 (3)
B2—B7—B859.6 (3)B16—B21—B2259.5 (3)
C0AA—B7—B1158.9 (3)B20—B21—B22107.4 (4)
B2—B7—B11107.3 (3)B15—B21—B22107.5 (4)
B8—B7—B11108.5 (4)C1AA—B21—H21125.7
C0AA—B7—B1104.2 (4)B16—B21—H21122.8
B2—B7—B160.3 (3)B20—B21—H21121.8
B8—B7—B1108.4 (4)B15—B21—H21122.7
B11—B7—B159.1 (3)B22—B21—H21121.8
C0AA—B7—H7125.0C1AA—B22—B17104.0 (4)
B2—B7—H7122.8C1AA—B22—B16103.9 (4)
B8—B7—H7121.0B17—B22—B1660.3 (3)
B11—B7—H7121.7C1AA—B22—B2358.2 (3)
B1—B7—H7122.5B17—B22—B2360.0 (3)
C0AA—B8—B2103.7 (4)B16—B22—B23108.0 (4)
C0AA—B8—B758.0 (3)C1AA—B22—B2158.7 (3)
B2—B8—B760.1 (3)B17—B22—B21108.3 (4)
C0AA—B8—B958.6 (3)B16—B22—B2159.8 (3)
B2—B8—B9107.6 (4)B23—B22—B21108.1 (4)
B7—B8—B9107.8 (4)C1AA—B22—H22125.5
C0AA—B8—B3103.8 (3)B17—B22—H22122.3
B2—B8—B359.7 (3)B16—B22—H22122.6
B7—B8—B3107.8 (4)B23—B22—H22121.5
B9—B8—B359.8 (3)B21—B22—H22121.2
C0AA—B8—H8125.6C1AA—B23—B1958.5 (3)
B2—B8—H8122.7C1AA—B23—B17104.4 (4)
B7—B8—H8121.5B19—B23—B17107.9 (4)
B9—B8—H8121.5C1AA—B23—B2259.1 (3)
B3—B8—H8122.7B19—B23—B22108.3 (4)
C0AA—B9—B4103.5 (4)B17—B23—B2259.7 (3)
C0AA—B9—B1058.0 (3)C1AA—B23—B13104.5 (4)
B4—B9—B1059.7 (3)B19—B23—B1359.8 (3)
C0AA—B9—B3103.9 (4)B17—B23—B1360.2 (3)
B4—B9—B359.9 (3)B22—B23—B13108.3 (4)
B10—B9—B3107.4 (4)C1AA—B23—H23124.9
C0AA—B9—B858.4 (3)B19—B23—H23121.5
B4—B9—B8107.9 (4)B17—B23—H23122.6
B10—B9—B8107.5 (4)B22—B23—H23121.2
B3—B9—B860.2 (3)B13—B23—H23122.3
C0AA—B9—H9125.6N1S—C1S—C2S179.4 (10)
B4—B9—H9122.7C1S—C2S—H2SC109.5
B10—B9—H9122.0C1S—C2S—H2SB109.5
B3—B9—H9122.5H2SC—C2S—H2SB109.5
B8—B9—H9121.4C1S—C2S—H2SA109.5
C0AA—B10—B4104.2 (3)H2SC—C2S—H2SA109.5
C0AA—B10—B1159.1 (3)H2SB—C2S—H2SA109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
B10—H10···Br8i1.122.853.612 (5)125
C1AA—H1A···Br4ii1.122.773.547 (5)126

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2197).

References

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  • Burns, R. M. & Hubbard, J. L. (1994). J. Am. Chem. Soc.116, 9514–9520.
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  • Pearsal, M., Gembicky, M., Dominiak, P., Larsen, A. & Coppens, P. (2007). Acta Cryst. E63, m2596.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stasko, D., Hoffmann, S. P., Kim, K.-C., Fackler, N. L. P., Larsen, A. S., Drovetskaya, T., Tham, F. S., Reed, C. A., Rickard, C. E. F. & Boyd, P. D. W. (2002). J. Am. Chem. Soc.124, 13869–13876. [PubMed]
  • Westrip, S. P. (2010). publCIF. In preparation.

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