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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Nov 13;64(Pt 12):m1535. doi: 10.1107/S1600536808036702

(Dithio­benzoato-κ2 S,S′)[hydridotris(pyrazol-1-yl-κN 2)borato](triphenyl­phosphine-κP)ruthenium(II)

Chia-Her Lin a, Yao-Ren Liang b, Hung-Chun Tong b, Yih Hsing Lo b,*, Ting Shen Kuo c
PMCID: PMC2960112  PMID: 21581150

Abstract

Reaction of [Ru(Tp)Cl(PPh3)2] (Tp = hydridotrispyrazolyl­borate) with ammonium dithio­benzoate in methanol leads to the formation of the title compound, [Ru(C9H10BN6)(C7H5S2)(C18H15P)]. In the crystal structure, the Ru atom is coordinated by three N atoms of the Tp ligand, one P atom of the triphenyl­phosphine ligand and the two S atoms of the dithio­benzoate ligand within a slightly distorted octa­hedron. The Ru—S bonds are slightly different [2.321 (1) and 2.396 (1) Å] and the average N—Ru—N angle is 86.31°.

Related literature

For general background, see: Alock et al. (1992 ▶); Burrows (2001 ▶); Pavlik et al. (2005 ▶); Hidai et al. (2000 ▶); Vit & Zdrazil (1989 ▶). For related structures, see: Gemel et al. (1996 ▶); Slugovc et al. (1998 ▶); Sellmann et al. (1999 ▶); Meno et al. (1995 ▶).graphic file with name e-64-m1535-scheme1.jpg

Experimental

Crystal data

  • [Ru(C9H10BN6)(C7H5S2)(C18H15P)]

  • M r = 729.61

  • Monoclinic, Inline graphic

  • a = 12.8915 (13) Å

  • b = 18.394 (2) Å

  • c = 13.5174 (16) Å

  • β = 96.591 (5)°

  • V = 3184.2 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.71 mm−1

  • T = 200 (2) K

  • 0.18 × 0.12 × 0.02 mm

Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.883, T max = 0.986

  • 22786 measured reflections

  • 5557 independent reflections

  • 3974 reflections with I > 2σ(I)

  • R int = 0.056

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036

  • wR(F 2) = 0.080

  • S = 1.02

  • 5557 reflections

  • 406 parameters

  • H-atom parameters constrained

  • Δρmax = 1.39 e Å−3

  • Δρmin = −0.62 e Å−3

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036702/nc2121sup1.cif

e-64-m1535-sup1.cif (24.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036702/nc2121Isup2.hkl

e-64-m1535-Isup2.hkl (266.6KB, hkl)

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

Acknowledgments

This research was supported by the National Science Council, Taiwan (NSC 97–2113-M-036–001-MY2) and in part by the Project of Specific Research Fields in Tatung University, Taiwan (B96—C07–081), and the Project of Specific Research Fields in Chung Yuan Christian University, Taiwan, under grant No. CYCU-97-CR—CH.

supplementary crystallographic information

Comment

Ruthenium(II) hydridotripyrazolylborate complexes, (Ru(Tp), are of interest for stoichiometric and catalytic transformations of organic molecules (Pavlik et al., 2005). The complex [Ru(Tp)Cl(PPh3)2] (Alock et al., 1992) has been used as the starting material for the synthesis of several complexes because the chloride atom and the phosphine ligand can easily be substituted (Burrows, 2001). On the other hand, the chemistry of transition metal sulfur compounds has attracted much interest for their importance in the field of catalysis and metalloenzymes (Hidai et al., 2000). In recent years there has been an increased interest in ruthenium sulfur complexes, in part because of the high catalytic activity of RuS2 in various hydrotreating processes (Vit & Zdrazil, 1989). Thus, many ruthenium thiolate complexes have been reported. However, ruthenium complexes with dithio ligands are relatively rare (Sellmann et al., 1999). In this context the structure of the title compound was determined.

In the crystal structure of the title compound, the Ru atom is coordinated by three N atoms of the Tp ligand, two S atoms of the dithiobenzoate ligand and one P atom of the triphenylphosphine ligand forming slightly distorted octahedron. The average N—Ru—N angle amount to 86.31° and the three Ru—N bond lengths of 2.141 (3), 2.098 (3) and 2.134 (3) Å are slightly longer than the average distance of 2.038 Å in observed in other RuTp complexes (Gemel et al.1996 and Slugovc et al.1998). The dithiobenzoate ligand chelates the ruthenium centre with slightly different Ru—S bonds of 2.321 (1) Å and and 2.396 (1) Å and an S—Ru—S angle of 71.61 (3)°. The average Ru—S bond length of 2.3588 (11) Å is slightly shorter than in cis-[Ru(S2CNEt2)2(PPh3)2] (av. 2.3952 (5) Å) (Meno et al., 1995).

Experimental

To a solution of [Ru(Tp)Cl(PPh3)2] (3.95 g, 4.50 mmol) in MeOH (20 ml) an excess of [NH4][S2C(C6H5)] (1.71 g, 10 mmol) were added. The reaction mixture was stirred for 4 h at room temperature. The solvent was removed in vacuum and 20 ml of CH2Cl2 were added to the residue. After filtration the solvent was removed in vacuum to give the title compound. Spectroscopic analysis: IR(KBr, cm-1): ν(BH)2467 cm-1.31P NMR(CDCl3, 303 K, δ,p.p.m.): d 58.3 (PPh3). MS (m/z,Ru102): 730.2 (M+), 468.1(M+ - PPh3). Anal. Calcd for C34H30BN6PRuS2: C, 55.97; H,4.14; N, 11.52. Found: C, 55.73; H, 4.11;N, 11.42. The bright-yellow crystals used for X-ray structure analysis were obtained by recrystallization of the crude product from dichloromethane–hexane.

Refinement

The H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C), B—H = 1.0 Å and Uiso(H) = 1.2Ueq(B).

Figures

Fig. 1.

Fig. 1.

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Molecular structure of the title compound with labelling and displacement ellipsoids drawn at the 30% probability level (H atoms are shown as spheres of arbitrary radius).

Crystal data

[Ru(C9H10BN6)(C7H5S2)(C18H15P)] F000 = 1488
Mr = 729.61 Dx = 1.522 Mg m−3
Monoclinic, P21/n Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 5326 reflections
a = 12.8915 (13) Å θ = 2.3–24.9º
b = 18.394 (2) Å µ = 0.71 mm−1
c = 13.5174 (16) Å T = 200 (2) K
β = 96.591 (5)º Prism, green
V = 3184.2 (6) Å3 0.18 × 0.12 × 0.02 mm
Z = 4
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Data collection

Nonius KappaCCD diffractometer 5557 independent reflections
Radiation source: fine-focus sealed tube 3974 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.056
T = 200(2) K θmax = 25.0º
CCD rotation images, thick slices scans θmin = 1.9º
Absorption correction: multi-scan(Blessing, 1995) h = −15→12
Tmin = 0.883, Tmax = 0.986 k = −21→20
22786 measured reflections l = −16→15
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036 H-atom parameters constrained
wR(F2) = 0.080   w = 1/[σ2(Fo2) + (0.0315P)2 + 1.684P] where P = (Fo2 + 2Fc2)/3
S = 1.02 (Δ/σ)max = 0.001
5557 reflections Δρmax = 1.39 e Å−3
406 parameters Δρmin = −0.62 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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Special details

Experimental. Semi-empirical from equivalents by WinGX (Blessing, 1995)
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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
B1 0.3330 (3) 0.7338 (2) 0.0521 (3) 0.0277 (11)
H1' 0.3875 0.7068 0.0198 0.033*
C1 0.3375 (3) 0.75212 (19) 0.3191 (3) 0.0272 (9)
H1 0.3096 0.7678 0.3777 0.033*
C2 0.4285 (3) 0.7130 (2) 0.3191 (3) 0.0331 (10)
H2 0.4739 0.6970 0.3752 0.040*
C3 0.4393 (3) 0.7023 (2) 0.2210 (3) 0.0283 (9)
H3 0.4949 0.6770 0.1959 0.034*
C4 0.2720 (3) 0.9240 (2) 0.0120 (3) 0.0282 (9)
H4 0.2359 0.9673 0.0255 0.034*
C5 0.3432 (3) 0.9186 (2) −0.0566 (3) 0.0334 (10)
H5 0.3648 0.9559 −0.0983 0.040*
C6 0.3760 (3) 0.8478 (2) −0.0514 (3) 0.0310 (10)
H6 0.4256 0.8267 −0.0897 0.037*
C7 0.0588 (3) 0.68809 (19) 0.0294 (3) 0.0259 (9)
H7 −0.0109 0.6970 0.0424 0.031*
C8 0.0901 (3) 0.6302 (2) −0.0258 (3) 0.0338 (10)
H8 0.0474 0.5927 −0.0570 0.041*
C9 0.1945 (3) 0.6385 (2) −0.0257 (3) 0.0327 (10)
H9 0.2389 0.6070 −0.0574 0.039*
C10 0.2846 (3) 0.98437 (19) 0.2445 (2) 0.0191 (8)
C11 0.2725 (3) 1.05912 (19) 0.2465 (3) 0.0243 (9)
H11 0.2057 1.0794 0.2525 0.029*
C12 0.3569 (3) 1.1045 (2) 0.2400 (3) 0.0298 (10)
H12 0.3478 1.1557 0.2408 0.036*
C13 0.4542 (3) 1.0757 (2) 0.2322 (3) 0.0279 (9)
H13 0.5124 1.1070 0.2287 0.034*
C14 0.4670 (3) 1.0014 (2) 0.2297 (3) 0.0280 (9)
H14 0.5341 0.9814 0.2242 0.034*
C15 0.3825 (3) 0.9555 (2) 0.2350 (3) 0.0241 (9)
H15 0.3916 0.9043 0.2323 0.029*
C16 0.2187 (3) 0.89959 (19) 0.3980 (3) 0.0218 (8)
C17 0.2997 (3) 0.9362 (2) 0.4538 (3) 0.0275 (9)
H17 0.3328 0.9756 0.4247 0.033*
C18 0.3329 (3) 0.9164 (2) 0.5511 (3) 0.0349 (10)
H18 0.3890 0.9418 0.5877 0.042*
C19 0.2853 (3) 0.8606 (2) 0.5942 (3) 0.0329 (10)
H19 0.3102 0.8460 0.6601 0.040*
C20 0.2015 (3) 0.8251 (2) 0.5433 (3) 0.0322 (10)
H20 0.1661 0.7878 0.5747 0.039*
C21 0.1693 (3) 0.8448 (2) 0.4452 (3) 0.0273 (9)
H21 0.1120 0.8200 0.4096 0.033*
C22 0.0647 (3) 0.97588 (18) 0.2688 (3) 0.0206 (8)
C23 0.0053 (3) 0.9746 (2) 0.3480 (3) 0.0301 (10)
H23 0.0297 0.9485 0.4068 0.036*
C24 −0.0893 (3) 1.0110 (2) 0.3421 (3) 0.0380 (11)
H24 −0.1290 1.0100 0.3971 0.046*
C25 −0.1262 (3) 1.0486 (2) 0.2574 (3) 0.0341 (10)
H25 −0.1921 1.0722 0.2530 0.041*
C26 −0.0671 (3) 1.0517 (2) 0.1791 (3) 0.0279 (9)
H26 −0.0913 1.0787 0.1212 0.034*
C27 0.0272 (3) 1.01580 (19) 0.1842 (3) 0.0228 (9)
H27 0.0673 1.0182 0.1295 0.027*
C28 −0.0643 (3) 0.83083 (19) 0.1494 (3) 0.0212 (8)
C29 −0.1777 (3) 0.83849 (19) 0.1434 (3) 0.0256 (9)
C30 −0.2313 (3) 0.8185 (2) 0.2228 (3) 0.0341 (10)
H30 −0.1940 0.8001 0.2822 0.041*
C31 −0.3392 (3) 0.8253 (3) 0.2156 (3) 0.0454 (12)
H31 −0.3755 0.8108 0.2697 0.055*
C32 −0.3936 (3) 0.8529 (2) 0.1303 (4) 0.0457 (12)
H32 −0.4673 0.8575 0.1258 0.055*
C33 −0.3420 (3) 0.8735 (2) 0.0523 (4) 0.0452 (12)
H33 −0.3801 0.8927 −0.0063 0.054*
C34 −0.2346 (3) 0.8668 (2) 0.0578 (3) 0.0334 (10)
H34 −0.1993 0.8815 0.0032 0.040*
N1 0.2933 (2) 0.76531 (15) 0.2267 (2) 0.0215 (7)
N2 0.3582 (2) 0.73352 (16) 0.1657 (2) 0.0235 (7)
N3 0.2606 (2) 0.86080 (16) 0.0565 (2) 0.0210 (7)
N4 0.3261 (2) 0.81318 (16) 0.0171 (2) 0.0241 (7)
N5 0.1408 (2) 0.72945 (15) 0.0615 (2) 0.0223 (7)
N6 0.2250 (2) 0.69857 (16) 0.0266 (2) 0.0251 (7)
P1 0.18113 (7) 0.91954 (5) 0.26504 (7) 0.0190 (2)
Ru1 0.16002 (2) 0.822395 (15) 0.15631 (2) 0.01805 (9)
S1 0.01327 (7) 0.78411 (5) 0.23709 (7) 0.0227 (2)
S2 0.00968 (7) 0.87056 (5) 0.06980 (7) 0.0231 (2)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
B1 0.025 (3) 0.031 (3) 0.028 (3) 0.005 (2) 0.006 (2) −0.001 (2)
C1 0.038 (3) 0.022 (2) 0.020 (2) 0.0017 (18) −0.0020 (18) 0.0005 (17)
C2 0.036 (3) 0.033 (2) 0.028 (2) 0.0073 (19) −0.0084 (19) 0.0016 (19)
C3 0.021 (2) 0.026 (2) 0.037 (3) 0.0045 (17) 0.0015 (18) 0.0056 (19)
C4 0.033 (2) 0.026 (2) 0.024 (2) −0.0042 (18) 0.0010 (18) 0.0035 (18)
C5 0.034 (3) 0.036 (3) 0.032 (2) −0.0045 (19) 0.0105 (19) 0.009 (2)
C6 0.025 (2) 0.047 (3) 0.023 (2) −0.0026 (19) 0.0100 (17) 0.0058 (19)
C7 0.028 (2) 0.025 (2) 0.024 (2) −0.0035 (18) 0.0006 (17) 0.0000 (17)
C8 0.037 (3) 0.029 (2) 0.033 (3) −0.0087 (19) −0.0037 (19) −0.004 (2)
C9 0.048 (3) 0.022 (2) 0.029 (2) 0.0042 (19) 0.004 (2) −0.0041 (19)
C10 0.017 (2) 0.023 (2) 0.018 (2) −0.0013 (16) 0.0032 (15) 0.0009 (16)
C11 0.020 (2) 0.025 (2) 0.028 (2) 0.0013 (16) 0.0048 (17) 0.0001 (18)
C12 0.035 (3) 0.019 (2) 0.036 (2) −0.0033 (18) 0.0028 (19) −0.0010 (18)
C13 0.027 (2) 0.030 (2) 0.027 (2) −0.0109 (18) 0.0061 (17) −0.0006 (18)
C14 0.021 (2) 0.032 (2) 0.032 (2) 0.0007 (17) 0.0050 (17) −0.0034 (19)
C15 0.027 (2) 0.020 (2) 0.025 (2) −0.0008 (17) 0.0032 (17) −0.0006 (17)
C16 0.024 (2) 0.024 (2) 0.018 (2) 0.0070 (16) 0.0031 (16) −0.0004 (16)
C17 0.025 (2) 0.031 (2) 0.026 (2) 0.0006 (17) 0.0016 (17) 0.0015 (19)
C18 0.029 (2) 0.046 (3) 0.028 (2) 0.004 (2) −0.0019 (18) −0.005 (2)
C19 0.035 (3) 0.043 (3) 0.020 (2) 0.015 (2) 0.0022 (19) 0.004 (2)
C20 0.041 (3) 0.032 (2) 0.024 (2) 0.007 (2) 0.0088 (19) 0.005 (2)
C21 0.031 (2) 0.028 (2) 0.022 (2) −0.0023 (17) 0.0015 (17) 0.0000 (17)
C22 0.020 (2) 0.0188 (19) 0.023 (2) −0.0035 (16) 0.0047 (16) −0.0039 (17)
C23 0.027 (2) 0.035 (2) 0.029 (2) 0.0039 (19) 0.0049 (18) 0.0014 (19)
C24 0.035 (3) 0.046 (3) 0.035 (3) 0.009 (2) 0.016 (2) 0.001 (2)
C25 0.021 (2) 0.040 (3) 0.042 (3) 0.0084 (18) 0.004 (2) −0.006 (2)
C26 0.027 (2) 0.026 (2) 0.030 (2) 0.0022 (17) −0.0036 (18) −0.0047 (18)
C27 0.023 (2) 0.024 (2) 0.023 (2) −0.0002 (16) 0.0053 (16) −0.0001 (17)
C28 0.021 (2) 0.023 (2) 0.020 (2) −0.0022 (16) 0.0010 (15) −0.0024 (17)
C29 0.019 (2) 0.023 (2) 0.034 (2) −0.0022 (16) 0.0034 (18) −0.0101 (18)
C30 0.025 (2) 0.050 (3) 0.028 (2) −0.003 (2) 0.0047 (18) −0.013 (2)
C31 0.030 (3) 0.068 (3) 0.041 (3) −0.004 (2) 0.015 (2) −0.025 (3)
C32 0.022 (3) 0.053 (3) 0.062 (3) 0.004 (2) 0.002 (2) −0.023 (3)
C33 0.031 (3) 0.043 (3) 0.059 (3) 0.004 (2) −0.007 (2) −0.004 (2)
C34 0.025 (3) 0.032 (2) 0.043 (3) 0.0008 (18) 0.0023 (19) 0.005 (2)
N1 0.0232 (18) 0.0173 (16) 0.0244 (18) −0.0015 (13) 0.0042 (14) 0.0000 (14)
N2 0.0193 (18) 0.0260 (17) 0.0255 (18) 0.0024 (14) 0.0047 (14) 0.0024 (15)
N3 0.0207 (18) 0.0228 (17) 0.0195 (17) −0.0011 (13) 0.0020 (13) 0.0022 (14)
N4 0.0198 (17) 0.0311 (19) 0.0218 (17) 0.0011 (14) 0.0043 (13) 0.0026 (15)
N5 0.0238 (19) 0.0212 (17) 0.0221 (17) 0.0006 (14) 0.0032 (14) −0.0026 (14)
N6 0.0270 (19) 0.0232 (18) 0.0257 (19) 0.0004 (14) 0.0067 (14) −0.0014 (14)
P1 0.0186 (5) 0.0182 (5) 0.0203 (5) −0.0001 (4) 0.0030 (4) 0.0008 (4)
Ru1 0.01702 (17) 0.01847 (15) 0.01893 (17) −0.00125 (13) 0.00328 (11) 0.00074 (14)
S1 0.0213 (5) 0.0233 (5) 0.0239 (5) −0.0014 (4) 0.0042 (4) 0.0021 (4)
S2 0.0216 (6) 0.0252 (5) 0.0225 (5) −0.0010 (4) 0.0016 (4) 0.0013 (4)
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Geometric parameters (Å, °)

B1—N2 1.533 (5) C18—C19 1.361 (5)
B1—N4 1.535 (5) C18—H18 0.9500
B1—N6 1.538 (5) C19—C20 1.378 (5)
B1—H1' 1.0000 C19—H19 0.9500
C1—N1 1.335 (4) C20—C21 1.391 (5)
C1—C2 1.376 (5) C20—H20 0.9500
C1—H1 0.9500 C21—H21 0.9500
C2—C3 1.363 (5) C22—C23 1.386 (5)
C2—H2 0.9500 C22—C27 1.398 (5)
C3—N2 1.342 (4) C22—P1 1.829 (4)
C3—H3 0.9500 C23—C24 1.386 (5)
C4—N3 1.325 (4) C23—H23 0.9500
C4—C5 1.382 (5) C24—C25 1.375 (5)
C4—H4 0.9500 C24—H24 0.9500
C5—C6 1.368 (5) C25—C26 1.375 (5)
C5—H5 0.9500 C25—H25 0.9500
C6—N4 1.347 (4) C26—C27 1.378 (5)
C6—H6 0.9500 C26—H26 0.9500
C7—N5 1.334 (4) C27—H27 0.9500
C7—C8 1.386 (5) C28—C29 1.461 (5)
C7—H7 0.9500 C28—S2 1.684 (4)
C8—C9 1.355 (5) C28—S1 1.694 (4)
C8—H8 0.9500 C29—C30 1.392 (5)
C9—N6 1.347 (5) C29—C34 1.397 (5)
C9—H9 0.9500 C30—C31 1.388 (5)
C10—C11 1.384 (5) C30—H30 0.9500
C10—C15 1.389 (5) C31—C32 1.376 (6)
C10—P1 1.834 (3) C31—H31 0.9500
C11—C12 1.383 (5) C32—C33 1.364 (6)
C11—H11 0.9500 C32—H32 0.9500
C12—C13 1.376 (5) C33—C34 1.384 (5)
C12—H12 0.9500 C33—H33 0.9500
C13—C14 1.379 (5) C34—H34 0.9500
C13—H13 0.9500 N1—N2 1.372 (4)
C14—C15 1.386 (5) N1—Ru1 2.141 (3)
C14—H14 0.9500 N3—N4 1.366 (4)
C15—H15 0.9500 N3—Ru1 2.098 (3)
C16—C21 1.387 (5) N5—N6 1.357 (4)
C16—C17 1.389 (5) N5—Ru1 2.134 (3)
C16—P1 1.844 (4) P1—Ru1 2.3100 (10)
C17—C18 1.384 (5) Ru1—S2 2.3213 (10)
C17—H17 0.9500 Ru1—S1 2.3962 (10)
N2—B1—N4 108.0 (3) C25—C24—C23 120.6 (4)
N2—B1—N6 107.8 (3) C25—C24—H24 119.7
N4—B1—N6 108.2 (3) C23—C24—H24 119.7
N2—B1—H1' 110.9 C26—C25—C24 119.5 (4)
N4—B1—H1' 110.9 C26—C25—H25 120.3
N6—B1—H1' 110.9 C24—C25—H25 120.3
N1—C1—C2 111.5 (3) C25—C26—C27 120.4 (4)
N1—C1—H1 124.2 C25—C26—H26 119.8
C2—C1—H1 124.2 C27—C26—H26 119.8
C3—C2—C1 104.9 (3) C26—C27—C22 120.8 (3)
C3—C2—H2 127.5 C26—C27—H27 119.6
C1—C2—H2 127.5 C22—C27—H27 119.6
N2—C3—C2 108.7 (3) C29—C28—S2 124.0 (3)
N2—C3—H3 125.7 C29—C28—S1 126.4 (3)
C2—C3—H3 125.7 S2—C28—S1 109.6 (2)
N3—C4—C5 110.9 (4) C30—C29—C34 118.5 (4)
N3—C4—H4 124.5 C30—C29—C28 121.0 (4)
C5—C4—H4 124.5 C34—C29—C28 120.6 (3)
C6—C5—C4 105.1 (3) C31—C30—C29 120.3 (4)
C6—C5—H5 127.5 C31—C30—H30 119.8
C4—C5—H5 127.5 C29—C30—H30 119.8
N4—C6—C5 108.4 (4) C32—C31—C30 120.1 (4)
N4—C6—H6 125.8 C32—C31—H31 119.9
C5—C6—H6 125.8 C30—C31—H31 119.9
N5—C7—C8 110.2 (3) C33—C32—C31 120.3 (4)
N5—C7—H7 124.9 C33—C32—H32 119.9
C8—C7—H7 124.9 C31—C32—H32 119.9
C9—C8—C7 105.3 (3) C32—C33—C34 120.4 (4)
C9—C8—H8 127.4 C32—C33—H33 119.8
C7—C8—H8 127.4 C34—C33—H33 119.8
N6—C9—C8 108.9 (4) C33—C34—C29 120.4 (4)
N6—C9—H9 125.6 C33—C34—H34 119.8
C8—C9—H9 125.6 C29—C34—H34 119.8
C11—C10—C15 119.1 (3) C1—N1—N2 105.1 (3)
C11—C10—P1 123.9 (3) C1—N1—Ru1 137.7 (2)
C15—C10—P1 116.7 (3) N2—N1—Ru1 117.1 (2)
C12—C11—C10 120.5 (3) C3—N2—N1 109.7 (3)
C12—C11—H11 119.7 C3—N2—B1 128.4 (3)
C10—C11—H11 119.7 N1—N2—B1 121.8 (3)
C13—C12—C11 120.2 (4) C4—N3—N4 106.3 (3)
C13—C12—H12 119.9 C4—N3—Ru1 134.1 (3)
C11—C12—H12 119.9 N4—N3—Ru1 119.3 (2)
C12—C13—C14 119.7 (3) C6—N4—N3 109.3 (3)
C12—C13—H13 120.1 C6—N4—B1 130.3 (3)
C14—C13—H13 120.1 N3—N4—B1 120.4 (3)
C13—C14—C15 120.4 (4) C7—N5—N6 106.5 (3)
C13—C14—H14 119.8 C7—N5—Ru1 133.3 (3)
C15—C14—H14 119.8 N6—N5—Ru1 120.1 (2)
C14—C15—C10 120.0 (3) C9—N6—N5 109.2 (3)
C14—C15—H15 120.0 C9—N6—B1 131.7 (3)
C10—C15—H15 120.0 N5—N6—B1 119.1 (3)
C21—C16—C17 117.3 (3) C22—P1—C10 104.42 (16)
C21—C16—P1 120.7 (3) C22—P1—C16 102.15 (16)
C17—C16—P1 122.0 (3) C10—P1—C16 99.36 (16)
C18—C17—C16 121.4 (4) C22—P1—Ru1 114.77 (11)
C18—C17—H17 119.3 C10—P1—Ru1 116.19 (12)
C16—C17—H17 119.3 C16—P1—Ru1 117.70 (12)
C19—C18—C17 120.0 (4) N3—Ru1—N5 85.49 (11)
C19—C18—H18 120.0 N3—Ru1—N1 85.83 (11)
C17—C18—H18 120.0 N5—Ru1—N1 84.61 (11)
C18—C19—C20 120.7 (4) N3—Ru1—P1 96.44 (8)
C18—C19—H19 119.7 N5—Ru1—P1 177.43 (8)
C20—C19—H19 119.7 N1—Ru1—P1 93.82 (8)
C19—C20—C21 118.9 (4) N3—Ru1—S2 95.15 (8)
C19—C20—H20 120.5 N5—Ru1—S2 88.31 (8)
C21—C20—H20 120.5 N1—Ru1—S2 172.76 (8)
C16—C21—C20 121.7 (4) P1—Ru1—S2 93.20 (3)
C16—C21—H21 119.2 N3—Ru1—S1 166.07 (8)
C20—C21—H21 119.2 N5—Ru1—S1 89.71 (8)
C23—C22—C27 118.1 (3) N1—Ru1—S1 106.76 (8)
C23—C22—P1 122.6 (3) P1—Ru1—S1 88.79 (3)
C27—C22—P1 118.8 (3) S2—Ru1—S1 71.61 (3)
C22—C23—C24 120.5 (4) C28—S1—Ru1 88.02 (12)
C22—C23—H23 119.7 C28—S2—Ru1 90.79 (12)
C24—C23—H23 119.7
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2121).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036702/nc2121sup1.cif

e-64-m1535-sup1.cif (24.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036702/nc2121Isup2.hkl

e-64-m1535-Isup2.hkl (266.6KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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