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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Nov 8;64(Pt 12):m1511–m1512. doi: 10.1107/S1600536808036039

Azido­(1,1-diphenyl­methanimine-κN)[hydridotris(pyrazolyl-κN 2)borato](triphenyl­phosphine-κP)ruthenium(II) diethyl ether solvate

Chia-Her Lin a, Ting-Shen Kuo b, Hung-Chun Tong c, Chih-Yung Chen Hsu c, Yih-Hsing Lo c,*
PMCID: PMC2960095  PMID: 21581130

Abstract

The reaction of [RuCl(C9H10BN6)(C18H15P)2] with benzo­phenone imine in methanol, in the presence of sodium azide, leads to the formation of the title compound, [Ru(C9H10BN6)(N3)(HN=CPh2)(C18H15P)]·C4H10O, which crystallizes as the diethyl ether solvate. In the crystal structure, the Ru atom is coordinated by three N atoms of one hydridotris(pyrazoly)borate anion, one P atom of one triphenyl­phosphine ligand, one N atom of the azide anion and one N atom of the benzophenone­imine ligand in a slightly distorted octa­hedral geometry. The azide anion is almost linear [177.0 (5)°], with an Ru—N—N angle of 125.9 (3)°. There is a small difference between the N—N distances [1.200 (5) and 1.164 (5) Å], the longer bond being adjacent to the Ru atom.

Related literature

For general background, see: Agrell (1971 ▶); Alcock et al. (1992 ▶); Burrows et al. (2001 ▶); Moloy & Petersen (1995 ▶); Pavlik et al. (2005 ▶); Slugovc et al. (1997 ▶); Trofimenko et al. (1993 ▶). For related structures, see: Dori & Ziolo (1973 ▶); Gemel et al. (1996 ▶); Meyer et al. (1998 ▶); Huynh et al. (2003 ▶); Slugovc et al. (1998 ▶).graphic file with name e-64-m1511-scheme1.jpg

Experimental

Crystal data

  • [Ru(C9H10BN6)(N3)(C13H11N)(C18H15P)]·C4H10O

  • M r = 873.76

  • Triclinic, Inline graphic

  • a = 11.7387 (12) Å

  • b = 13.0535 (13) Å

  • c = 14.7187 (15) Å

  • α = 70.445 (2)°

  • β = 81.716 (2)°

  • γ = 88.040 (3)°

  • V = 2102.9 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.46 mm−1

  • T = 200 (2) K

  • 0.19 × 0.07 × 0.02 mm

Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.918, T max = 0.989

  • 16858 measured reflections

  • 7382 independent reflections

  • 4895 reflections with I > 2σ(I)

  • R int = 0.061

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050

  • wR(F 2) = 0.113

  • S = 1.01

  • 7382 reflections

  • 523 parameters

  • H-atom parameters constrained

  • Δρmax = 1.75 e Å−3

  • Δρmin = −0.56 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997 ▶); data reduction: HKL 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 publication routines (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036039/nc2120sup1.cif

e-64-m1511-sup1.cif (28.6KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036039/nc2120Isup2.hkl

e-64-m1511-Isup2.hkl (353.9KB, 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 of Tatung University, Taiwan (B96-C07-081) and the project of specific research fields in Chung Yuan Christian University, Taiwan (under grant CYCU-97-CR-CH).

supplementary crystallographic information

Comment

The hydridotris(pyrazoly)borate anion (Tp,HB(pz)3) has been used by Trofimenko as a ligand in various transition metal complexes (Trofimenko,1993). 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 PPh3 group can be easily substituted (Slugovc et al., 1997; Moloy & Petersen, 1995; Burrows, 2001). On the other hand, the azide anion N3- is a versatile ligand because it shows a variety of coordination modes and compounds with this ligand shows interesting thermal and photochemical reactivities (Dori & Ziolo, 1973; Meyer et al., 1998; Huynh et al., 2003).

In the crystal structure of the title compound, the environment about the ruthenium metal center corresponds to a slightly distorted octahedron and the bite angle of the Tp ligand leads to an average N—Ru1—N angle of 86.3°, which is only slightly distorted from 90° (Fig. 1). The three Ru1—N(Tp) bond lengths of 2.077 (3), 2.114 (4), and 2.084 (4) Å) are slightly longer than the average distance of 2.038 Å observed in other ruthenium Tp complexes (Gemel et al. 1996; Slugovc et al. 1998). The Ru1—N7 and N7—C10 bond lengths of 2.053 (3) and 1.304 (5) Å correspond to a single Ru—N and a double C=N bond. The angles around C10 of 122.3 (4)°, 118.6 (4)° and 119.1 (4)° indicate a sp2 hybridization.

The azide anion is almost linear (177.0 (5)°) and is coordinated to Ru with an Ru—N(8)—N(9) angle of 125.9 (3)°. There is a small difference between the N—N distances [1.200 (5) and 1.164 (5) Å], the longer being adjacent to the Ru atom. It is also noted the title complex shows a νas(N3) stretching band in a lower energy region, at 2036 cm-1,compared with the typical values of these bands in azido complexes (2120–2030 cm-1; Agrell, 1971).

Experimental

To a solution of [Ru(Tp)Cl(PPh3)2] (3.95 g, 4.50 mmol) in CH3OH (100 ml), an excess of benzophenoneimine (7.9 ml, 45.0 mmol) and NaN3 (2.93 g, 45.0 mmol) were added and the solution was refluxed for 120 min. Afterwards the reaction mixture was concentrated to approximately 10 ml and cooled to 253 K. The yellow precipitate which has formed was filtered off, washed with CH2Cl2and was dried under reduced pressure to give the title compound (2.34 g, 65% yield). The bright-yellow crystals used for X-ray structure analysis were obtained within 3 days by slow diffusion of diethyl ether into a solution of the title compound in CH2Cl2 at 273 K.

Refinement

The H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H = 0.95 - 0.99 Å and Uiso(H) = 1.2 or 1.5Ueq(C), B—H = 1.0 Å and Uiso(H) = 1.2Ueq(B), and N—H = 0.88 Å and Uiso(H) = 1.2Ueq(N).

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)(N3)(C13H11N)(C18H15P)]·C4H10O Z = 2
Mr = 873.76 F000 = 904
Triclinic, P1 Dx = 1.380 Mg m−3
Hall symbol: -P 1 Mo Kα radiation λ = 0.71073 Å
a = 11.7387 (12) Å Cell parameters from 16922 reflections
b = 13.0535 (13) Å θ = 2.4–22.8º
c = 14.7187 (15) Å µ = 0.46 mm−1
α = 70.445 (2)º T = 200 (2) K
β = 81.716 (2)º Prism, red
γ = 88.040 (3)º 0.19 × 0.07 × 0.02 mm
V = 2102.9 (4) Å3
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Data collection

Nonius KappaCCD diffractometer 7382 independent reflections
Radiation source: fine-focus sealed tube 4895 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.061
T = 200(2) K θmax = 25.0º
CCD rotation images, thick slices scans θmin = 1.5º
Absorption correction: multi-scan(Blessing, 1995) h = −10→13
Tmin = 0.918, Tmax = 0.989 k = −13→15
16858 measured reflections l = −16→17
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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)] = 0.050 H-atom parameters constrained
wR(F2) = 0.113   w = 1/[σ2(Fo2) + (0.0454P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01 (Δ/σ)max = 0.001
7382 reflections Δρmax = 1.75 e Å−3
523 parameters Δρmin = −0.56 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
B1 0.8157 (5) 0.8932 (4) 0.7251 (4) 0.0386 (15)
H1' 0.8125 0.9641 0.7376 0.046*
C1 0.8247 (4) 0.8636 (4) 0.4879 (3) 0.0354 (12)
H1 0.8285 0.8213 0.4462 0.043*
C2 0.8292 (4) 0.9767 (4) 0.4569 (4) 0.0424 (13)
H2 0.8359 1.0254 0.3918 0.051*
C3 0.8219 (4) 1.0027 (4) 0.5398 (4) 0.0427 (13)
H3 0.8236 1.0743 0.5426 0.051*
C4 1.0523 (4) 0.7072 (4) 0.7588 (3) 0.0367 (12)
H4 1.0886 0.6421 0.7554 0.044*
C5 1.1011 (4) 0.7847 (4) 0.7874 (3) 0.0426 (13)
H5 1.1747 0.7834 0.8073 0.051*
C6 1.0193 (4) 0.8638 (4) 0.7806 (3) 0.0405 (13)
H6 1.0270 0.9292 0.7942 0.049*
C7 0.6070 (4) 0.6735 (4) 0.8423 (3) 0.0395 (13)
H7 0.5763 0.6032 0.8535 0.047*
C8 0.5601 (5) 0.7450 (4) 0.8884 (4) 0.0517 (15)
H8 0.4938 0.7336 0.9363 0.062*
C9 0.6287 (5) 0.8348 (4) 0.8508 (4) 0.0464 (14)
H9 0.6189 0.8990 0.8677 0.056*
C10 0.8495 (4) 0.4452 (3) 0.8627 (3) 0.0290 (11)
C11 0.8971 (4) 0.3351 (3) 0.8753 (3) 0.0315 (11)
C12 0.8898 (4) 0.2849 (4) 0.8067 (4) 0.0390 (12)
H12 0.8505 0.3203 0.7527 0.047*
C13 0.9382 (5) 0.1845 (4) 0.8150 (4) 0.0497 (14)
H13 0.9317 0.1516 0.7673 0.060*
C14 0.9959 (5) 0.1326 (4) 0.8926 (4) 0.0495 (15)
H14 1.0297 0.0639 0.8986 0.059*
C15 1.0041 (4) 0.1810 (4) 0.9615 (4) 0.0470 (14)
H15 1.0442 0.1453 1.0148 0.056*
C16 0.9548 (4) 0.2809 (4) 0.9540 (3) 0.0374 (12)
H16 0.9603 0.3126 1.0027 0.045*
C17 0.8004 (4) 0.4727 (3) 0.9494 (3) 0.0298 (11)
C18 0.7310 (4) 0.3970 (4) 1.0255 (3) 0.0362 (12)
H18 0.7154 0.3280 1.0211 0.043*
C19 0.6847 (4) 0.4219 (4) 1.1073 (4) 0.0461 (14)
H19 0.6373 0.3698 1.1585 0.055*
C20 0.7062 (4) 0.5207 (4) 1.1154 (4) 0.0475 (14)
H20 0.6737 0.5374 1.1716 0.057*
C21 0.7757 (5) 0.5958 (4) 1.0410 (4) 0.0484 (14)
H21 0.7913 0.6645 1.0461 0.058*
C22 0.8228 (4) 0.5716 (4) 0.9591 (3) 0.0417 (13)
H22 0.8712 0.6236 0.9087 0.050*
C23 0.5401 (4) 0.6507 (3) 0.6241 (3) 0.0265 (10)
C24 0.5229 (4) 0.7597 (4) 0.6139 (3) 0.0334 (11)
H24 0.5853 0.8036 0.6149 0.040*
C25 0.4153 (4) 0.8042 (4) 0.6023 (3) 0.0389 (12)
H25 0.4046 0.8792 0.5933 0.047*
C26 0.3236 (4) 0.7410 (4) 0.6035 (3) 0.0371 (12)
H26 0.2497 0.7722 0.5958 0.045*
C27 0.3386 (4) 0.6325 (4) 0.6157 (3) 0.0352 (12)
H27 0.2752 0.5884 0.6172 0.042*
C28 0.4466 (4) 0.5878 (3) 0.6259 (3) 0.0313 (11)
H28 0.4568 0.5129 0.6343 0.038*
C29 0.7223 (4) 0.6166 (3) 0.4899 (3) 0.0281 (11)
C30 0.6531 (4) 0.6761 (3) 0.4225 (3) 0.0352 (12)
H30 0.5815 0.7024 0.4443 0.042*
C31 0.6870 (5) 0.6977 (4) 0.3238 (3) 0.0422 (13)
H31 0.6388 0.7389 0.2783 0.051*
C32 0.7903 (5) 0.6598 (4) 0.2913 (4) 0.0428 (13)
H32 0.8144 0.6762 0.2235 0.051*
C33 0.8588 (4) 0.5977 (4) 0.3579 (4) 0.0377 (12)
H33 0.9287 0.5689 0.3359 0.045*
C34 0.8257 (4) 0.5776 (3) 0.4555 (3) 0.0299 (11)
H34 0.8742 0.5364 0.5006 0.036*
C35 0.6572 (4) 0.4502 (3) 0.6762 (3) 0.0253 (10)
C36 0.6827 (4) 0.3772 (3) 0.6266 (3) 0.0337 (12)
H36 0.7174 0.4026 0.5605 0.040*
C37 0.6578 (4) 0.2664 (4) 0.6728 (4) 0.0381 (12)
H37 0.6774 0.2170 0.6383 0.046*
C38 0.6057 (4) 0.2287 (4) 0.7670 (4) 0.0401 (13)
H38 0.5869 0.1536 0.7976 0.048*
C39 0.5806 (4) 0.3003 (4) 0.8176 (3) 0.0400 (13)
H39 0.5448 0.2743 0.8834 0.048*
C40 0.6073 (4) 0.4101 (4) 0.7731 (3) 0.0360 (12)
H40 0.5912 0.4584 0.8092 0.043*
C41 0.3203 (7) 0.0075 (7) 0.9844 (5) 0.120 (3)
H41A 0.2559 −0.0211 1.0365 0.180*
H41B 0.3228 0.0870 0.9648 0.180*
H41C 0.3926 −0.0218 1.0078 0.180*
C42 0.3049 (6) −0.0244 (6) 0.9012 (5) 0.092 (2)
H42A 0.3008 −0.1047 0.9212 0.110*
H42B 0.2315 0.0047 0.8779 0.110*
C43 0.3815 (7) −0.0031 (5) 0.7392 (5) 0.088 (2)
H43A 0.3098 0.0316 0.7164 0.105*
H43B 0.3744 −0.0822 0.7518 0.105*
C44 0.4811 (6) 0.0426 (5) 0.6632 (5) 0.086 (2)
H44A 0.4699 0.0298 0.6031 0.128*
H44B 0.5517 0.0073 0.6856 0.128*
H44C 0.4874 0.1210 0.6505 0.128*
N1 0.8145 (3) 0.8235 (3) 0.5848 (3) 0.0284 (9)
N2 0.8118 (3) 0.9105 (3) 0.6168 (3) 0.0306 (9)
N3 0.9472 (3) 0.7371 (3) 0.7369 (2) 0.0291 (9)
N4 0.9270 (3) 0.8335 (3) 0.7515 (3) 0.0327 (9)
N5 0.7002 (3) 0.7161 (3) 0.7804 (3) 0.0299 (9)
N6 0.7130 (3) 0.8180 (3) 0.7856 (3) 0.0338 (9)
N7 0.8548 (3) 0.5152 (3) 0.7752 (3) 0.0303 (9)
H7A 0.8889 0.4811 0.7365 0.036*
N8 0.9577 (3) 0.6233 (3) 0.5978 (3) 0.0336 (10)
N9 1.0225 (3) 0.6845 (3) 0.5335 (3) 0.0347 (10)
N10 1.0865 (4) 0.7402 (3) 0.4696 (4) 0.0632 (15)
O1 0.3970 (3) 0.0154 (3) 0.8253 (3) 0.0591 (10)
P1 0.68709 (10) 0.59726 (9) 0.62088 (8) 0.0255 (3)
Ru1 0.82112 (3) 0.66797 (3) 0.68486 (3) 0.02500 (12)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
B1 0.045 (4) 0.035 (3) 0.041 (4) 0.000 (3) −0.006 (3) −0.019 (3)
C1 0.045 (3) 0.033 (3) 0.025 (3) −0.002 (2) −0.004 (2) −0.006 (2)
C2 0.056 (4) 0.030 (3) 0.030 (3) −0.003 (2) −0.005 (3) 0.004 (2)
C3 0.050 (3) 0.023 (3) 0.050 (4) 0.000 (2) −0.010 (3) −0.003 (2)
C4 0.032 (3) 0.041 (3) 0.026 (3) 0.000 (2) 0.000 (2) 0.000 (2)
C5 0.032 (3) 0.061 (3) 0.031 (3) −0.011 (3) −0.006 (2) −0.010 (3)
C6 0.041 (3) 0.050 (3) 0.030 (3) −0.018 (3) −0.002 (2) −0.013 (3)
C7 0.033 (3) 0.054 (3) 0.033 (3) −0.011 (3) 0.004 (2) −0.018 (3)
C8 0.040 (3) 0.072 (4) 0.052 (4) −0.004 (3) 0.008 (3) −0.040 (3)
C9 0.046 (3) 0.054 (3) 0.054 (4) 0.004 (3) −0.003 (3) −0.040 (3)
C10 0.023 (3) 0.032 (3) 0.028 (3) −0.002 (2) −0.005 (2) −0.004 (2)
C11 0.026 (3) 0.030 (3) 0.034 (3) −0.003 (2) −0.002 (2) −0.005 (2)
C12 0.040 (3) 0.034 (3) 0.039 (3) 0.001 (2) −0.010 (3) −0.007 (2)
C13 0.062 (4) 0.031 (3) 0.057 (4) −0.001 (3) −0.005 (3) −0.017 (3)
C14 0.053 (4) 0.032 (3) 0.055 (4) 0.008 (3) −0.004 (3) −0.007 (3)
C15 0.048 (3) 0.043 (3) 0.038 (3) 0.010 (3) −0.007 (3) 0.003 (3)
C16 0.041 (3) 0.038 (3) 0.028 (3) 0.005 (2) −0.006 (2) −0.004 (2)
C17 0.029 (3) 0.033 (3) 0.024 (3) −0.002 (2) −0.006 (2) −0.003 (2)
C18 0.031 (3) 0.036 (3) 0.037 (3) −0.002 (2) −0.003 (2) −0.007 (2)
C19 0.039 (3) 0.052 (3) 0.038 (3) −0.006 (3) 0.007 (3) −0.007 (3)
C20 0.045 (3) 0.065 (4) 0.034 (3) 0.002 (3) 0.000 (3) −0.020 (3)
C21 0.062 (4) 0.047 (3) 0.038 (3) −0.013 (3) 0.000 (3) −0.018 (3)
C22 0.049 (3) 0.041 (3) 0.031 (3) −0.013 (3) −0.002 (3) −0.005 (2)
C23 0.030 (3) 0.031 (2) 0.017 (2) 0.002 (2) −0.001 (2) −0.008 (2)
C24 0.034 (3) 0.037 (3) 0.034 (3) −0.002 (2) −0.004 (2) −0.016 (2)
C25 0.044 (3) 0.034 (3) 0.039 (3) 0.013 (2) −0.009 (3) −0.012 (2)
C26 0.029 (3) 0.048 (3) 0.033 (3) 0.007 (2) −0.003 (2) −0.014 (3)
C27 0.030 (3) 0.045 (3) 0.032 (3) −0.004 (2) 0.000 (2) −0.017 (2)
C28 0.036 (3) 0.028 (2) 0.026 (3) 0.000 (2) 0.000 (2) −0.007 (2)
C29 0.037 (3) 0.020 (2) 0.025 (3) −0.004 (2) 0.001 (2) −0.007 (2)
C30 0.038 (3) 0.034 (3) 0.032 (3) 0.000 (2) −0.005 (2) −0.009 (2)
C31 0.053 (4) 0.043 (3) 0.027 (3) 0.001 (3) −0.009 (3) −0.006 (2)
C32 0.057 (4) 0.045 (3) 0.023 (3) −0.010 (3) 0.008 (3) −0.011 (2)
C33 0.038 (3) 0.038 (3) 0.036 (3) −0.002 (2) 0.009 (3) −0.016 (2)
C34 0.033 (3) 0.032 (3) 0.025 (3) −0.002 (2) −0.005 (2) −0.010 (2)
C35 0.025 (2) 0.024 (2) 0.028 (3) 0.0003 (19) −0.004 (2) −0.011 (2)
C36 0.039 (3) 0.028 (3) 0.028 (3) −0.004 (2) 0.000 (2) −0.004 (2)
C37 0.046 (3) 0.030 (3) 0.042 (3) −0.003 (2) −0.005 (3) −0.019 (2)
C38 0.051 (3) 0.024 (3) 0.043 (3) −0.005 (2) −0.008 (3) −0.007 (2)
C39 0.052 (3) 0.038 (3) 0.022 (3) −0.009 (3) 0.001 (2) −0.003 (2)
C40 0.046 (3) 0.032 (3) 0.028 (3) −0.004 (2) 0.002 (2) −0.010 (2)
C41 0.107 (7) 0.195 (9) 0.076 (6) −0.029 (6) 0.016 (5) −0.079 (6)
C42 0.066 (5) 0.120 (6) 0.096 (6) −0.022 (4) 0.010 (4) −0.052 (5)
C43 0.117 (6) 0.081 (5) 0.077 (5) −0.035 (4) −0.011 (5) −0.040 (4)
C44 0.135 (7) 0.058 (4) 0.061 (5) −0.026 (4) −0.006 (5) −0.017 (3)
N1 0.030 (2) 0.024 (2) 0.030 (2) 0.0015 (17) −0.0039 (18) −0.0082 (18)
N2 0.038 (2) 0.022 (2) 0.032 (2) −0.0003 (17) −0.0050 (19) −0.0090 (18)
N3 0.028 (2) 0.032 (2) 0.023 (2) −0.0001 (18) −0.0013 (18) −0.0033 (18)
N4 0.040 (2) 0.029 (2) 0.030 (2) −0.0026 (19) −0.0062 (19) −0.0100 (18)
N5 0.028 (2) 0.036 (2) 0.029 (2) 0.0026 (18) −0.0040 (18) −0.0154 (19)
N6 0.034 (2) 0.036 (2) 0.037 (2) 0.0011 (19) −0.003 (2) −0.021 (2)
N7 0.031 (2) 0.030 (2) 0.029 (2) −0.0027 (17) −0.0010 (18) −0.0105 (19)
N8 0.035 (2) 0.028 (2) 0.031 (2) 0.0002 (19) 0.008 (2) −0.0052 (19)
N9 0.030 (2) 0.036 (2) 0.044 (3) 0.006 (2) −0.007 (2) −0.021 (2)
N10 0.051 (3) 0.050 (3) 0.074 (4) −0.013 (2) 0.029 (3) −0.014 (3)
O1 0.061 (3) 0.061 (2) 0.062 (3) 0.004 (2) −0.009 (2) −0.030 (2)
P1 0.0300 (7) 0.0231 (6) 0.0225 (7) 0.0018 (5) −0.0013 (5) −0.0075 (5)
Ru1 0.0269 (2) 0.0245 (2) 0.0208 (2) 0.00069 (15) −0.00016 (16) −0.00537 (16)
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Geometric parameters (Å, °)

B1—N4 1.529 (7) C25—H25 0.9500
B1—N2 1.541 (6) C26—C27 1.374 (6)
B1—N6 1.548 (6) C26—H26 0.9500
B1—H1' 1.0000 C27—C28 1.384 (6)
C1—N1 1.333 (5) C27—H27 0.9500
C1—C2 1.392 (6) C28—H28 0.9500
C1—H1 0.9500 C29—C30 1.386 (6)
C2—C3 1.362 (6) C29—C34 1.393 (6)
C2—H2 0.9500 C29—P1 1.845 (4)
C3—N2 1.344 (5) C30—C31 1.384 (6)
C3—H3 0.9500 C30—H30 0.9500
C4—N3 1.333 (5) C31—C32 1.377 (7)
C4—C5 1.386 (6) C31—H31 0.9500
C4—H4 0.9500 C32—C33 1.384 (7)
C5—C6 1.374 (6) C32—H32 0.9500
C5—H5 0.9500 C33—C34 1.371 (6)
C6—N4 1.337 (5) C33—H33 0.9500
C6—H6 0.9500 C34—H34 0.9500
C7—N5 1.323 (5) C35—C36 1.384 (6)
C7—C8 1.385 (6) C35—C40 1.390 (6)
C7—H7 0.9500 C35—P1 1.840 (4)
C8—C9 1.353 (7) C36—C37 1.398 (6)
C8—H8 0.9500 C36—H36 0.9500
C9—N6 1.342 (5) C37—C38 1.363 (6)
C9—H9 0.9500 C37—H37 0.9500
C10—N7 1.299 (5) C38—C39 1.378 (6)
C10—C17 1.473 (6) C38—H38 0.9500
C10—C11 1.487 (6) C39—C40 1.387 (6)
C11—C12 1.389 (6) C39—H39 0.9500
C11—C16 1.395 (6) C40—H40 0.9500
C12—C13 1.384 (6) C41—C42 1.454 (8)
C12—H12 0.9500 C41—H41A 0.9800
C13—C14 1.376 (7) C41—H41B 0.9800
C13—H13 0.9500 C41—H41C 0.9800
C14—C15 1.378 (7) C42—O1 1.411 (7)
C14—H14 0.9500 C42—H42A 0.9900
C15—C16 1.385 (6) C42—H42B 0.9900
C15—H15 0.9500 C43—O1 1.405 (7)
C16—H16 0.9500 C43—C44 1.483 (8)
C17—C22 1.383 (6) C43—H43A 0.9900
C17—C18 1.395 (6) C43—H43B 0.9900
C18—C19 1.382 (6) C44—H44A 0.9800
C18—H18 0.9500 C44—H44B 0.9800
C19—C20 1.369 (7) C44—H44C 0.9800
C19—H19 0.9500 N1—N2 1.366 (4)
C20—C21 1.380 (7) N1—Ru1 2.077 (3)
C20—H20 0.9500 N3—N4 1.354 (5)
C21—C22 1.382 (6) N3—Ru1 2.114 (4)
C21—H21 0.9500 N5—N6 1.372 (5)
C22—H22 0.9500 N5—Ru1 2.084 (4)
C23—C28 1.384 (6) N7—Ru1 2.056 (3)
C23—C24 1.389 (6) N7—H7A 0.8800
C23—P1 1.840 (4) N8—N9 1.200 (5)
C24—C25 1.382 (6) N8—Ru1 2.097 (4)
C24—H24 0.9500 N9—N10 1.164 (5)
C25—C26 1.373 (6) P1—Ru1 2.3070 (13)
N4—B1—N2 107.3 (4) C30—C31—H31 119.9
N4—B1—N6 108.1 (4) C31—C32—C33 119.7 (5)
N2—B1—N6 107.8 (4) C31—C32—H32 120.1
N4—B1—H1' 111.1 C33—C32—H32 120.1
N2—B1—H1' 111.1 C34—C33—C32 120.0 (5)
N6—B1—H1' 111.1 C34—C33—H33 120.0
N1—C1—C2 110.0 (4) C32—C33—H33 120.0
N1—C1—H1 125.0 C33—C34—C29 121.2 (4)
C2—C1—H1 125.0 C33—C34—H34 119.4
C3—C2—C1 105.3 (4) C29—C34—H34 119.4
C3—C2—H2 127.3 C36—C35—C40 118.1 (4)
C1—C2—H2 127.3 C36—C35—P1 123.5 (3)
N2—C3—C2 108.8 (4) C40—C35—P1 118.4 (3)
N2—C3—H3 125.6 C35—C36—C37 120.7 (4)
C2—C3—H3 125.6 C35—C36—H36 119.7
N3—C4—C5 110.2 (5) C37—C36—H36 119.7
N3—C4—H4 124.9 C38—C37—C36 120.5 (4)
C5—C4—H4 124.9 C38—C37—H37 119.7
C6—C5—C4 104.7 (4) C36—C37—H37 119.7
C6—C5—H5 127.6 C37—C38—C39 119.5 (4)
C4—C5—H5 127.6 C37—C38—H38 120.3
N4—C6—C5 108.7 (4) C39—C38—H38 120.3
N4—C6—H6 125.6 C38—C39—C40 120.5 (4)
C5—C6—H6 125.6 C38—C39—H39 119.8
N5—C7—C8 111.0 (5) C40—C39—H39 119.8
N5—C7—H7 124.5 C39—C40—C35 120.7 (4)
C8—C7—H7 124.5 C39—C40—H40 119.6
C9—C8—C7 105.3 (5) C35—C40—H40 119.6
C9—C8—H8 127.4 C42—C41—H41A 109.5
C7—C8—H8 127.4 C42—C41—H41B 109.5
N6—C9—C8 108.7 (4) H41A—C41—H41B 109.5
N6—C9—H9 125.7 C42—C41—H41C 109.5
C8—C9—H9 125.7 H41A—C41—H41C 109.5
N7—C10—C17 122.0 (4) H41B—C41—H41C 109.5
N7—C10—C11 118.8 (4) O1—C42—C41 110.5 (6)
C17—C10—C11 119.2 (4) O1—C42—H42A 109.6
C12—C11—C16 117.9 (4) C41—C42—H42A 109.6
C12—C11—C10 120.9 (4) O1—C42—H42B 109.6
C16—C11—C10 121.2 (4) C41—C42—H42B 109.6
C13—C12—C11 121.7 (5) H42A—C42—H42B 108.1
C13—C12—H12 119.2 O1—C43—C44 109.7 (6)
C11—C12—H12 119.2 O1—C43—H43A 109.7
C14—C13—C12 119.7 (5) C44—C43—H43A 109.7
C14—C13—H13 120.1 O1—C43—H43B 109.7
C12—C13—H13 120.1 C44—C43—H43B 109.7
C13—C14—C15 119.5 (5) H43A—C43—H43B 108.2
C13—C14—H14 120.2 C43—C44—H44A 109.5
C15—C14—H14 120.2 C43—C44—H44B 109.5
C14—C15—C16 121.0 (5) H44A—C44—H44B 109.5
C14—C15—H15 119.5 C43—C44—H44C 109.5
C16—C15—H15 119.5 H44A—C44—H44C 109.5
C15—C16—C11 120.2 (5) H44B—C44—H44C 109.5
C15—C16—H16 119.9 C1—N1—N2 106.6 (3)
C11—C16—H16 119.9 C1—N1—Ru1 134.0 (3)
C22—C17—C18 118.2 (4) N2—N1—Ru1 118.9 (3)
C22—C17—C10 121.9 (4) C3—N2—N1 109.2 (4)
C18—C17—C10 119.9 (4) C3—N2—B1 129.8 (4)
C19—C18—C17 120.4 (4) N1—N2—B1 120.3 (4)
C19—C18—H18 119.8 C4—N3—N4 106.8 (4)
C17—C18—H18 119.8 C4—N3—Ru1 133.6 (3)
C20—C19—C18 120.9 (5) N4—N3—Ru1 119.6 (3)
C20—C19—H19 119.6 C6—N4—N3 109.5 (4)
C18—C19—H19 119.6 C6—N4—B1 131.0 (4)
C19—C20—C21 119.3 (5) N3—N4—B1 119.2 (4)
C19—C20—H20 120.3 C7—N5—N6 105.6 (4)
C21—C20—H20 120.3 C7—N5—Ru1 136.8 (3)
C20—C21—C22 120.3 (5) N6—N5—Ru1 117.6 (3)
C20—C21—H21 119.9 C9—N6—N5 109.5 (4)
C22—C21—H21 119.9 C9—N6—B1 129.2 (4)
C21—C22—C17 121.0 (4) N5—N6—B1 121.3 (4)
C21—C22—H22 119.5 C10—N7—Ru1 149.3 (3)
C17—C22—H22 119.5 C10—N7—H7A 105.4
C28—C23—C24 118.6 (4) Ru1—N7—H7A 105.4
C28—C23—P1 121.3 (3) N9—N8—Ru1 125.9 (3)
C24—C23—P1 119.7 (3) N10—N9—N8 176.9 (5)
C25—C24—C23 120.1 (4) C43—O1—C42 113.3 (5)
C25—C24—H24 120.0 C23—P1—C35 100.84 (19)
C23—C24—H24 120.0 C23—P1—C29 100.2 (2)
C26—C25—C24 120.6 (4) C35—P1—C29 103.21 (19)
C26—C25—H25 119.7 C23—P1—Ru1 118.60 (15)
C24—C25—H25 119.7 C35—P1—Ru1 116.39 (14)
C25—C26—C27 119.9 (5) C29—P1—Ru1 115.06 (14)
C25—C26—H26 120.0 N7—Ru1—N1 170.95 (14)
C27—C26—H26 120.0 N7—Ru1—N5 99.27 (14)
C26—C27—C28 119.7 (5) N1—Ru1—N5 88.06 (14)
C26—C27—H27 120.1 N7—Ru1—N8 79.20 (14)
C28—C27—H27 120.1 N1—Ru1—N8 92.89 (14)
C23—C28—C27 121.0 (4) N5—Ru1—N8 173.15 (15)
C23—C28—H28 119.5 N7—Ru1—N3 90.87 (14)
C27—C28—H28 119.5 N1—Ru1—N3 84.22 (14)
C30—C29—C34 118.1 (4) N5—Ru1—N3 86.64 (14)
C30—C29—P1 122.1 (4) N8—Ru1—N3 86.71 (15)
C34—C29—P1 119.6 (3) N7—Ru1—P1 90.93 (10)
C31—C30—C29 120.8 (5) N1—Ru1—P1 93.73 (10)
C31—C30—H30 119.6 N5—Ru1—P1 94.99 (10)
C29—C30—H30 119.6 N8—Ru1—P1 91.71 (11)
C32—C31—C30 120.1 (5) N3—Ru1—P1 177.35 (10)
C32—C31—H31 119.9
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2120).

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/S1600536808036039/nc2120sup1.cif

e-64-m1511-sup1.cif (28.6KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036039/nc2120Isup2.hkl

e-64-m1511-Isup2.hkl (353.9KB, 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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