[1,4-Bis(diphenyl­phosphan­yl)butane-κ2P,P′]chlorido(η5-inden­yl)ruthenium(II)

Sung, H.-L.; Her, T.-M.; Su, W.-H.; Cheng, C.-P.

doi:10.1107/S1600536811015121

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page m641

doi:10.1107/S1600536811015121

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[1,4-Bis(diphenylphosphanyl)butane-κ²P,P′]chlorido(η⁵-indenyl)ruthenium(II)

Hui-Ling Sung,^a ^* Tze-Min Her,^b Wen-Hsien Su ^b and Chin-Pao Cheng ^c

^aDepartment of Mathematics and Science (Pre-college), National Taiwan Normal University, Taiwan, ^bDepartment of Chemical and Materials Engineering, Lunghwa University of Science and Technology, Taiwan, and ^cDepartment of Mechatronic Technology, National Taiwan Normal University, Taiwan
^*Correspondence e-mail: hlsung@ntnu.edu.tw

(Received 6 February 2011; accepted 21 April 2011; online 29 April 2011)

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 Ru^II 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 ).

Experimental

Crystal data

[Ru(C₉H₇)Cl(C₂₈H₂₈P₂)]
M_r = 678.11
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.102
S = 0.91
5443 reflections
370 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015121/bv2178sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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 et al. (19894).

Experimental top

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, J_P—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.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); 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).

Figures top

Fig. 1. View of the title compound showing displacement ellipsoids at the 30% probability level. H atom are omitted for clarity.

[1,4-Bis(diphenylphosphanyl)butane-κ²P,P']chlorido(η⁵- indenyl)ruthenium(II) top

Crystal data top

[Ru(C₉H₇)Cl(C₂₈H₂₈P₂)]	F(000) = 1392
M_r = 678.11	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0707P)² + 0.5716P] where P = (F_o² + 2F_c²)/3
5443 reflections	(Δ/σ)_max < 0.001
370 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

[Ru(C₉H₇)Cl(C₂₈H₂₈P₂)]	V = 3094.42 (10) Å³
M_r = 678.11	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.6567 (2) Å	µ = 0.72 mm⁻¹
b = 15.7502 (3) Å	T = 200 K
c = 15.9419 (3) Å	0.55 × 0.48 × 0.38 mm
β = 103.165 (1)°

Data collection top

Nonius KappaCCD diffractometer	5443 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4355 reflections with I > 2σ(I)
T_min = 0.704, T_max = 0.821	R_int = 0.060
18461 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 0.91	Δρ_max = 0.36 e Å⁻³
5443 reflections	Δρ_min = −0.71 e Å⁻³
370 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[Ru(C₉H₇)Cl(C₂₈H₂₈P₂)]
M_r	678.11
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	12.6567 (2), 15.7502 (3), 15.9419 (3)
β (°)	103.165 (1)
V (Å³)	3094.42 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.55 × 0.48 × 0.38

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.704, 0.821
No. of measured, independent and observed [I > 2σ(I)] reflections	18461, 5443, 4355
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.102, 0.91
No. of reflections	5443
No. of parameters	370
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.71

Computer programs: COLLECT (Nonius, 1998), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Acknowledgements

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.

References

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