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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Apr 29;67(Pt 5):m641. doi: 10.1107/S1600536811015121

[1,4-Bis(diphenyl­phosphan­yl)butane-κ2 P,P′]chlorido(η5-inden­yl)ruthenium(II)

Hui-Ling Sung a,*, Tze-Min Her b, Wen-Hsien Su b, Chin-Pao Cheng c
PMCID: PMC3089106  PMID: 21754349

Abstract

Facile ligand substitution is observed when the ruthenium chloride complex [Ru(η5-C9H7)Cl(PPh3)2] is treated with 1,4-bis­(diphenyl­phosphan­yl)butane in refluxing toluene yielding the title compound, [Ru(C9H7)Cl(C28H28P2)]. The RuII atom has a typical piano-stool coordination, defined by the indenyl ligand, one Cl atom and two phosphanyl P atoms. The Ru—P bond lengths are 2.2502 (9) and 2.2968 (8) Å.

Related literature

For general background to the title compound and other [Ru(η5-C9H7)Cl(diphos)] compounds, see: Oro et al. (1985 ▶); Tanase et al. (1994 ▶). For the chemistry of [Ru(η5-C9H7)Cl(diphos)], see: Franco (1989 ▶).graphic file with name e-67-0m641-scheme1.jpg

Experimental

Crystal data

  • [Ru(C9H7)Cl(C28H28P2)]

  • M r = 678.11

  • Monoclinic, Inline graphic

  • a = 12.6567 (2) Å

  • b = 15.7502 (3) Å

  • c = 15.9419 (3) Å

  • β = 103.165 (1)°

  • V = 3094.42 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.72 mm−1

  • T = 200 K

  • 0.55 × 0.48 × 0.38 mm

Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.704, T max = 0.821

  • 18461 measured reflections

  • 5443 independent reflections

  • 4355 reflections with I > 2σ(I)

  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035

  • wR(F 2) = 0.102

  • S = 0.91

  • 5443 reflections

  • 370 parameters

  • H-atom parameters constrained

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.71 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/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 global, I. DOI: 10.1107/S1600536811015121/bv2178sup1.cif

e-67-0m641-sup1.cif (25.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015121/bv2178Isup2.hkl

e-67-0m641-Isup2.hkl (261.1KB, hkl)

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

Acknowledgments

The authors are grateful to the National Science Council of the Republic of China (NSC grant No. 99-2221-E-003-003) and National Taiwan Normal University (grant No. 99031012) for financial support. The authors also thank Mr Ting Shen Kuo (Department of Chemistry, National Taiwan Normal University) for his assistance with the X-ray single-crystal structure analysis.

supplementary crystallographic information

Comment

Reaction of [Ru(η5-C9H7)Cl(diphos)] with phenylacetylene in the presence of alcoholic KOH yielded ruthenium acetylide complexes [Ru(η5-C9H7)(η1-CCPh)((diphos)] (diphos =1,2-bis(diphenylphosphanyl)butane (dppe), 1,2-bis(diphenylphosphanyl)butane (dppp), 1,2-bis(diphenylphosphanyl)butane (dppb)) in good yield (Tanase et al., 1994). Treatment of the complex [Ru(η5-C9H7)Cl(PPh3)2] with 1,2-bis(diphenylphosphanyl)butane in toluene afforded the title compound [Ru(η5-C9H7)Cl(dppb)] (Figure 1). In the crystal structure of the title compound, the bidentate ligand dppb is coordinated to Ru with an P—Ru—P angle of 94.88 (3)°. The Ru—P bond lengths are 2.2502 (9) and 2.2968 (8) Å, respectively.

Experimental

The title compound was prepared by a similar method used for the dppe ligand in the previous literature procedure of Oro, et al. (1985) The red-brown crystals of the title compound for X-ray structure analysis were obtained by slow diffusion of diethyl ether into a CH2Cl2 solution at room temperature for 3 days. Spectroscopic analysis: 1H NMR (CDCl3, 298 K, δ, p.p.m.): 7.48 — 7.13 (m, 24H, 20H of Ph and 4H of indenyl group); 4.49 (br, 1H of indenyl group); 3.82 (br, 2H of indenyl group); 3.21, 2.03, 1.80, 1.52 (m, 2H each one, CH2 of dppb). 31P{1H} NMR (CDCl3, 298 K, δ, p.p.m.): 49.5. 13C{1H} NMR (CDCl3, 298 K, δ, p.p.m.): 137.0 —128.4 (Ph); 122.6 (C-5, 6); 121.5 (C-4, 7); 115.7 (C-2); 99.7 (C-1, 3), 31.8 (t, two PCH2 of dppb, JP—C= 1.30 Hz); 27.4 (s, two CH2 of dppb). HRMS (ESI, m/z): 678.2 (M+). Anal. Calcd for C37H35 P2ClRu: C: 65.53, H: 5.20, Found: C: 65.58, H: 5.23.

Refinement

All H atoms were initially located in a difference map, but were constrained to an idealized geometry. Constrained bond lengths and isotropic displacement parameters: C—H = 0.95 Å and Uiso(H) = 1.2 Ueq(C) for aromatic H atoms, and C—H = 0.99 Å and Uiso(H) = 1.2 Ueq(C) for methylene.

Figures

Fig. 1.

Fig. 1.

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View of the title compound showing displacement ellipsoids at the 30% probability level. H atom are omitted for clarity.

Crystal data

[Ru(C9H7)Cl(C28H28P2)] F(000) = 1392
Mr = 678.11 Dx = 1.456 Mg m−3
Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 13485 reflections
a = 12.6567 (2) Å θ = 2.0–25.0°
b = 15.7502 (3) Å µ = 0.72 mm−1
c = 15.9419 (3) Å T = 200 K
β = 103.165 (1)° Prism, red–brown
V = 3094.42 (10) Å3 0.55 × 0.48 × 0.38 mm
Z = 4
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Data collection

Nonius KappaCCD diffractometer 5443 independent reflections
Radiation source: fine-focus sealed tube 4355 reflections with I > 2σ(I)
graphite Rint = 0.060
Detector resolution: 9 pixels mm-1 θmax = 25.0°, θmin = 2.9°
CCD rotation images, thick slices scans h = −14→15
Absorption correction: multi-scan (SADABS; Bruker, 2005) k = −18→18
Tmin = 0.704, Tmax = 0.821 l = −18→18
18461 measured reflections
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102 H-atom parameters constrained
S = 0.91 w = 1/[σ2(Fo2) + (0.0707P)2 + 0.5716P] where P = (Fo2 + 2Fc2)/3
5443 reflections (Δ/σ)max < 0.001
370 parameters Δρmax = 0.36 e Å−3
0 restraints Δρmin = −0.71 e Å−3
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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
C1 0.9824 (3) 0.0561 (2) 0.6534 (2) 0.0310 (7)
C2 1.0539 (3) 0.0051 (2) 0.7111 (2) 0.0416 (9)
H2 1.0262 −0.0376 0.7423 0.050*
C3 1.1652 (3) 0.0158 (3) 0.7235 (2) 0.0492 (10)
H3 1.2134 −0.0188 0.7638 0.059*
C4 1.2059 (3) 0.0773 (3) 0.6769 (3) 0.0485 (10)
H4 1.2821 0.0844 0.6849 0.058*
C5 1.1364 (3) 0.1276 (2) 0.6196 (3) 0.0457 (9)
H5 1.1644 0.1698 0.5881 0.055*
C6 1.0246 (3) 0.1170 (2) 0.6073 (2) 0.0375 (8)
H6 0.9768 0.1518 0.5669 0.045*
C7 0.7758 (2) 0.1115 (2) 0.5546 (2) 0.0308 (7)
C8 0.7854 (3) 0.0919 (2) 0.4711 (2) 0.0367 (8)
H8 0.8231 0.0420 0.4612 0.044*
C9 0.7405 (3) 0.1445 (2) 0.4029 (2) 0.0415 (9)
H9 0.7477 0.1309 0.3464 0.050*
C10 0.6851 (3) 0.2169 (2) 0.4166 (3) 0.0478 (9)
H10 0.6539 0.2529 0.3696 0.057*
C11 0.6753 (3) 0.2367 (2) 0.4985 (2) 0.0470 (9)
H11 0.6376 0.2866 0.5081 0.056*
C12 0.7198 (3) 0.1845 (2) 0.5667 (2) 0.0392 (8)
H12 0.7120 0.1987 0.6229 0.047*
C13 0.8163 (3) −0.06514 (19) 0.6006 (2) 0.0344 (8)
H13A 0.8628 −0.0708 0.5587 0.041*
H13B 0.8445 −0.1055 0.6481 0.041*
C14 0.7023 (3) −0.0944 (2) 0.5559 (2) 0.0373 (8)
H14A 0.6736 −0.0546 0.5080 0.045*
H14B 0.7084 −0.1508 0.5300 0.045*
C15 0.6194 (3) −0.1009 (2) 0.6115 (2) 0.0387 (8)
H15A 0.6553 −0.1269 0.6673 0.046*
H15B 0.5608 −0.1398 0.5829 0.046*
C16 0.5680 (3) −0.0169 (2) 0.6296 (2) 0.0333 (8)
H16A 0.4890 −0.0258 0.6224 0.040*
H16B 0.5781 0.0252 0.5859 0.040*
C17 0.5251 (2) 0.1131 (2) 0.7400 (2) 0.0325 (8)
C18 0.4995 (3) 0.1697 (2) 0.6714 (3) 0.0486 (10)
H18 0.5268 0.1602 0.6214 0.058*
C19 0.4349 (3) 0.2393 (3) 0.6752 (3) 0.0653 (13)
H19 0.4189 0.2778 0.6282 0.078*
C20 0.3931 (3) 0.2536 (3) 0.7471 (3) 0.0618 (12)
H20 0.3500 0.3024 0.7499 0.074*
C21 0.4144 (3) 0.1970 (3) 0.8142 (3) 0.0505 (10)
H21 0.3844 0.2057 0.8631 0.061*
C22 0.4798 (3) 0.1269 (2) 0.8105 (2) 0.0378 (8)
H22 0.4939 0.0877 0.8569 0.045*
C23 0.5811 (3) −0.05033 (19) 0.8083 (2) 0.0288 (7)
C24 0.4915 (3) −0.1027 (2) 0.7832 (2) 0.0385 (8)
H24 0.4519 −0.1021 0.7250 0.046*
C25 0.4590 (3) −0.1557 (2) 0.8414 (3) 0.0495 (10)
H25 0.3979 −0.1917 0.8230 0.059*
C26 0.5150 (3) −0.1566 (2) 0.9261 (2) 0.0479 (10)
H26 0.4920 −0.1928 0.9662 0.058*
C27 0.6037 (3) −0.1055 (2) 0.9528 (3) 0.0474 (9)
H27 0.6418 −0.1058 1.0115 0.057*
C28 0.6382 (3) −0.0532 (2) 0.8944 (2) 0.0372 (8)
H28 0.7011 −0.0191 0.9130 0.045*
C29 0.7860 (3) 0.1711 (2) 0.8823 (2) 0.0338 (8)
C30 0.7742 (3) 0.2060 (2) 0.7974 (2) 0.0371 (8)
H30 0.7118 0.2411 0.7658 0.045*
C31 0.8750 (3) 0.1951 (2) 0.7732 (3) 0.0432 (9)
H31 0.8948 0.2215 0.7218 0.052*
C32 0.9457 (3) 0.1465 (2) 0.8371 (2) 0.0440 (9)
H32 1.0228 0.1317 0.8380 0.053*
C33 0.8911 (3) 0.1335 (2) 0.9061 (2) 0.0368 (8)
C34 0.9246 (3) 0.0927 (2) 0.9869 (3) 0.0490 (10)
H34 0.9951 0.0686 1.0038 0.059*
C35 0.8541 (4) 0.0886 (3) 1.0400 (3) 0.0541 (11)
H35 0.8751 0.0594 1.0934 0.065*
C36 0.7508 (3) 0.1267 (3) 1.0172 (2) 0.0551 (11)
H36 0.7038 0.1234 1.0558 0.066*
C37 0.7170 (3) 0.1684 (2) 0.9408 (2) 0.0412 (9)
H37 0.6480 0.1953 0.9271 0.049*
Ru1 0.800240 (19) 0.071649 (15) 0.775247 (16) 0.02673 (11)
P1 0.83580 (7) 0.04314 (5) 0.64612 (5) 0.0283 (2)
P2 0.62274 (6) 0.02764 (5) 0.73711 (5) 0.0266 (2)
Cl1 0.85934 (7) −0.07244 (5) 0.82062 (5) 0.0343 (2)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0251 (17) 0.0342 (18) 0.0342 (18) 0.0036 (14) 0.0077 (14) −0.0051 (15)
C2 0.0318 (19) 0.052 (2) 0.042 (2) 0.0030 (17) 0.0106 (16) 0.0007 (18)
C3 0.035 (2) 0.066 (3) 0.045 (2) 0.014 (2) 0.0067 (17) −0.005 (2)
C4 0.0260 (19) 0.061 (3) 0.061 (3) −0.0005 (18) 0.0146 (18) −0.021 (2)
C5 0.038 (2) 0.043 (2) 0.060 (2) −0.0085 (18) 0.0201 (19) −0.0107 (19)
C6 0.0314 (19) 0.0367 (19) 0.047 (2) −0.0018 (15) 0.0137 (16) −0.0041 (17)
C7 0.0242 (17) 0.0314 (18) 0.0376 (18) −0.0022 (14) 0.0087 (14) 0.0053 (15)
C8 0.038 (2) 0.0350 (19) 0.037 (2) −0.0002 (15) 0.0075 (16) 0.0020 (16)
C9 0.038 (2) 0.048 (2) 0.038 (2) −0.0024 (17) 0.0059 (16) 0.0065 (17)
C10 0.042 (2) 0.049 (2) 0.050 (2) 0.0052 (19) 0.0044 (18) 0.0139 (19)
C11 0.041 (2) 0.045 (2) 0.058 (2) 0.0146 (17) 0.0168 (18) 0.0140 (19)
C12 0.0338 (19) 0.040 (2) 0.046 (2) 0.0034 (16) 0.0132 (16) 0.0079 (17)
C13 0.039 (2) 0.0301 (18) 0.0333 (19) 0.0057 (15) 0.0070 (15) −0.0001 (15)
C14 0.049 (2) 0.0268 (17) 0.0370 (19) −0.0065 (16) 0.0119 (17) −0.0082 (15)
C15 0.048 (2) 0.0295 (17) 0.0388 (19) −0.0092 (16) 0.0103 (17) −0.0013 (16)
C16 0.0325 (18) 0.0366 (19) 0.0288 (17) −0.0044 (15) 0.0024 (14) 0.0011 (15)
C17 0.0227 (17) 0.0271 (17) 0.046 (2) −0.0022 (14) 0.0042 (15) −0.0005 (16)
C18 0.038 (2) 0.042 (2) 0.070 (3) 0.0121 (17) 0.0211 (19) 0.020 (2)
C19 0.060 (3) 0.045 (2) 0.099 (4) 0.019 (2) 0.036 (3) 0.031 (2)
C20 0.044 (2) 0.041 (2) 0.100 (4) 0.0171 (19) 0.017 (2) 0.002 (2)
C21 0.041 (2) 0.051 (2) 0.059 (3) 0.0117 (19) 0.0079 (19) −0.011 (2)
C22 0.0329 (19) 0.041 (2) 0.0368 (19) 0.0056 (16) 0.0019 (15) −0.0053 (16)
C23 0.0267 (17) 0.0256 (16) 0.0351 (18) 0.0004 (13) 0.0089 (14) 0.0027 (14)
C24 0.0356 (19) 0.0381 (19) 0.042 (2) −0.0059 (16) 0.0096 (16) 0.0016 (17)
C25 0.052 (2) 0.046 (2) 0.057 (3) −0.0180 (19) 0.026 (2) −0.0033 (19)
C26 0.060 (3) 0.042 (2) 0.049 (2) −0.0032 (19) 0.028 (2) 0.0087 (18)
C27 0.054 (2) 0.049 (2) 0.042 (2) 0.004 (2) 0.0167 (19) 0.0056 (18)
C28 0.039 (2) 0.0377 (19) 0.0352 (19) −0.0007 (16) 0.0086 (16) 0.0039 (15)
C29 0.0290 (18) 0.0273 (17) 0.043 (2) −0.0038 (14) 0.0033 (15) −0.0153 (15)
C30 0.0365 (19) 0.0246 (17) 0.048 (2) 0.0007 (15) 0.0049 (16) −0.0097 (16)
C31 0.043 (2) 0.0296 (18) 0.061 (2) −0.0099 (16) 0.0204 (19) −0.0128 (18)
C32 0.0247 (18) 0.045 (2) 0.062 (2) −0.0120 (16) 0.0086 (17) −0.0266 (19)
C33 0.0263 (17) 0.0338 (18) 0.046 (2) −0.0023 (15) −0.0015 (15) −0.0188 (16)
C34 0.050 (2) 0.038 (2) 0.049 (2) 0.0065 (18) −0.0089 (19) −0.0206 (18)
C35 0.067 (3) 0.053 (2) 0.034 (2) 0.004 (2) −0.006 (2) −0.0154 (18)
C36 0.058 (3) 0.068 (3) 0.040 (2) −0.011 (2) 0.013 (2) −0.021 (2)
C37 0.0307 (19) 0.051 (2) 0.042 (2) −0.0026 (16) 0.0072 (16) −0.0208 (18)
Ru1 0.02312 (16) 0.02491 (16) 0.03191 (17) −0.00150 (10) 0.00574 (11) −0.00442 (11)
P1 0.0259 (4) 0.0272 (4) 0.0325 (5) 0.0015 (3) 0.0077 (4) −0.0010 (4)
P2 0.0232 (4) 0.0249 (4) 0.0310 (4) −0.0009 (3) 0.0051 (3) 0.0006 (4)
Cl1 0.0347 (5) 0.0317 (4) 0.0342 (4) 0.0046 (3) 0.0031 (3) 0.0011 (3)
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Geometric parameters (Å, °)

C1—C2 1.389 (5) C19—H19 0.9500
C1—C6 1.387 (5) C20—C21 1.371 (6)
C1—P1 1.844 (3) C20—H20 0.9500
C2—C3 1.388 (5) C21—C22 1.390 (5)
C2—H2 0.9500 C21—H21 0.9500
C3—C4 1.389 (6) C22—H22 0.9500
C3—H3 0.9500 C23—C24 1.385 (5)
C4—C5 1.367 (5) C23—C28 1.399 (5)
C4—H4 0.9500 C23—P2 1.829 (3)
C5—C6 1.394 (5) C24—C25 1.379 (5)
C5—H5 0.9500 C24—H24 0.9500
C6—H6 0.9500 C25—C26 1.374 (5)
C7—C12 1.387 (5) C25—H25 0.9500
C7—C8 1.398 (5) C26—C27 1.369 (5)
C7—P1 1.833 (3) C26—H26 0.9500
C8—C9 1.383 (5) C27—C28 1.384 (5)
C8—H8 0.9500 C27—H27 0.9500
C9—C10 1.381 (5) C28—H28 0.9500
C9—H9 0.9500 C29—C37 1.416 (5)
C10—C11 1.376 (5) C29—C33 1.427 (4)
C10—H10 0.9500 C29—C30 1.438 (5)
C11—C12 1.377 (5) C29—Ru1 2.354 (3)
C11—H11 0.9500 C30—C31 1.424 (5)
C12—H12 0.9500 C30—Ru1 2.183 (3)
C13—C14 1.528 (5) C30—H30 1.0000
C13—P1 1.848 (3) C31—C32 1.417 (5)
C13—H13A 0.9900 C31—Ru1 2.165 (3)
C13—H13B 0.9900 C31—H31 1.0000
C14—C15 1.524 (5) C32—C33 1.441 (5)
C14—H14A 0.9900 C32—Ru1 2.219 (3)
C14—H14B 0.9900 C32—H32 1.0000
C15—C16 1.530 (5) C33—C34 1.414 (5)
C15—H15A 0.9900 C33—Ru1 2.352 (3)
C15—H15B 0.9900 C34—C35 1.365 (6)
C16—P2 1.836 (3) C34—H34 0.9500
C16—H16A 0.9900 C35—C36 1.410 (6)
C16—H16B 0.9900 C35—H35 0.9500
C17—C22 1.389 (5) C36—C37 1.363 (5)
C17—C18 1.390 (5) C36—H36 0.9500
C17—P2 1.835 (3) C37—H37 0.9500
C18—C19 1.377 (5) Ru1—P1 2.2502 (9)
C18—H18 0.9500 Ru1—P2 2.2968 (8)
C19—C20 1.386 (6) Ru1—Cl1 2.4467 (8)
C2—C1—C6 118.6 (3) C25—C26—H26 119.9
C2—C1—P1 118.2 (2) C26—C27—C28 120.1 (4)
C6—C1—P1 123.1 (3) C26—C27—H27 119.9
C3—C2—C1 120.8 (3) C28—C27—H27 119.9
C3—C2—H2 119.6 C27—C28—C23 120.5 (3)
C1—C2—H2 119.6 C27—C28—H28 119.7
C2—C3—C4 119.7 (4) C23—C28—H28 119.7
C2—C3—H3 120.1 C37—C29—C33 119.4 (3)
C4—C3—H3 120.1 C37—C29—C30 133.2 (3)
C5—C4—C3 120.0 (3) C33—C29—C30 107.4 (3)
C5—C4—H4 120.0 C37—C29—Ru1 128.2 (2)
C3—C4—H4 120.0 C33—C29—Ru1 72.28 (17)
C4—C5—C6 120.2 (4) C30—C29—Ru1 65.16 (17)
C4—C5—H5 119.9 C31—C30—C29 107.6 (3)
C6—C5—H5 119.9 C31—C30—Ru1 70.21 (18)
C1—C6—C5 120.6 (3) C29—C30—Ru1 78.12 (18)
C1—C6—H6 119.7 C31—C30—H30 125.8
C5—C6—H6 119.7 C29—C30—H30 125.8
C12—C7—C8 118.3 (3) Ru1—C30—H30 125.8
C12—C7—P1 120.5 (3) C32—C31—C30 109.2 (3)
C8—C7—P1 121.2 (3) C32—C31—Ru1 73.2 (2)
C9—C8—C7 120.4 (3) C30—C31—Ru1 71.56 (19)
C9—C8—H8 119.8 C32—C31—H31 125.3
C7—C8—H8 119.8 C30—C31—H31 125.3
C8—C9—C10 120.2 (3) Ru1—C31—H31 125.3
C8—C9—H9 119.9 C31—C32—C33 107.0 (3)
C10—C9—H9 119.9 C31—C32—Ru1 69.11 (19)
C11—C10—C9 119.7 (3) C33—C32—Ru1 76.74 (18)
C11—C10—H10 120.1 C31—C32—H32 126.2
C9—C10—H10 120.1 C33—C32—H32 126.2
C12—C11—C10 120.4 (4) Ru1—C32—H32 126.2
C12—C11—H11 119.8 C34—C33—C29 119.9 (3)
C10—C11—H11 119.8 C34—C33—C32 131.6 (3)
C11—C12—C7 121.0 (3) C29—C33—C32 108.5 (3)
C11—C12—H12 119.5 C34—C33—Ru1 127.2 (2)
C7—C12—H12 119.5 C29—C33—Ru1 72.41 (18)
C14—C13—P1 119.3 (2) C32—C33—Ru1 66.65 (18)
C14—C13—H13A 107.5 C35—C34—C33 118.9 (4)
P1—C13—H13A 107.5 C35—C34—H34 120.5
C14—C13—H13B 107.5 C33—C34—H34 120.5
P1—C13—H13B 107.5 C34—C35—C36 121.3 (4)
H13A—C13—H13B 107.0 C34—C35—H35 119.4
C15—C14—C13 116.7 (3) C36—C35—H35 119.4
C15—C14—H14A 108.1 C37—C36—C35 121.3 (4)
C13—C14—H14A 108.1 C37—C36—H36 119.3
C15—C14—H14B 108.1 C35—C36—H36 119.3
C13—C14—H14B 108.1 C36—C37—C29 119.2 (3)
H14A—C14—H14B 107.3 C36—C37—H37 120.4
C14—C15—C16 115.5 (3) C29—C37—H37 120.4
C14—C15—H15A 108.4 C31—Ru1—C30 38.23 (12)
C16—C15—H15A 108.4 C31—Ru1—C32 37.69 (14)
C14—C15—H15B 108.4 C30—Ru1—C32 63.48 (13)
C16—C15—H15B 108.4 C31—Ru1—P1 89.21 (10)
H15A—C15—H15B 107.5 C30—Ru1—P1 114.21 (10)
C15—C16—P2 114.8 (2) C32—Ru1—P1 101.18 (10)
C15—C16—H16A 108.6 C31—Ru1—P2 132.17 (10)
P2—C16—H16A 108.6 C30—Ru1—P2 99.27 (9)
C15—C16—H16B 108.6 C32—Ru1—P2 160.13 (9)
P2—C16—H16B 108.6 P1—Ru1—P2 94.88 (3)
H16A—C16—H16B 107.5 C31—Ru1—C33 60.97 (14)
C22—C17—C18 118.0 (3) C30—Ru1—C33 61.09 (12)
C22—C17—P2 122.6 (3) C32—Ru1—C33 36.61 (12)
C18—C17—P2 119.2 (3) P1—Ru1—C33 137.29 (9)
C19—C18—C17 120.7 (4) P2—Ru1—C33 127.67 (9)
C19—C18—H18 119.7 C31—Ru1—C29 61.28 (13)
C17—C18—H18 119.7 C30—Ru1—C29 36.72 (12)
C18—C19—C20 120.5 (4) C32—Ru1—C29 61.13 (12)
C18—C19—H19 119.7 P1—Ru1—C29 149.38 (9)
C20—C19—H19 119.7 P2—Ru1—C29 99.26 (8)
C21—C20—C19 119.7 (4) C33—Ru1—C29 35.31 (11)
C21—C20—H20 120.1 C31—Ru1—Cl1 137.05 (11)
C19—C20—H20 120.1 C30—Ru1—Cl1 154.00 (10)
C20—C21—C22 119.7 (4) C32—Ru1—Cl1 101.22 (11)
C20—C21—H21 120.2 P1—Ru1—Cl1 88.51 (3)
C22—C21—H21 120.2 P2—Ru1—Cl1 90.75 (3)
C21—C22—C17 121.3 (3) C33—Ru1—Cl1 93.83 (9)
C21—C22—H22 119.4 C29—Ru1—Cl1 118.14 (9)
C17—C22—H22 119.4 C7—P1—C1 102.34 (15)
C24—C23—C28 118.0 (3) C7—P1—C13 103.63 (16)
C24—C23—P2 123.6 (3) C1—P1—C13 99.75 (15)
C28—C23—P2 118.2 (2) C7—P1—Ru1 118.56 (11)
C25—C24—C23 121.1 (3) C1—P1—Ru1 109.17 (11)
C25—C24—H24 119.4 C13—P1—Ru1 120.43 (11)
C23—C24—H24 119.4 C23—P2—C16 102.80 (15)
C26—C25—C24 120.1 (4) C23—P2—C17 100.73 (14)
C26—C25—H25 120.0 C16—P2—C17 101.01 (15)
C24—C25—H25 120.0 C23—P2—Ru1 116.19 (11)
C27—C26—C25 120.1 (3) C16—P2—Ru1 120.06 (11)
C27—C26—H26 119.9 C17—P2—Ru1 113.29 (10)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2178).

References

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  2. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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  7. 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.
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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 global, I. DOI: 10.1107/S1600536811015121/bv2178sup1.cif

e-67-0m641-sup1.cif (25.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015121/bv2178Isup2.hkl

e-67-0m641-Isup2.hkl (261.1KB, 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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