Dichlorido(η6-toluene)[tris­(4-methoxy­phen­yl)phosphine]ruthenium(II)

Wang, L.; Zhou, X.-G.; Li, R.-X.

doi:10.1107/S1600536808002341

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m429

doi:10.1107/S1600536808002341

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Dichlorido(η⁶-toluene)[tris(4-methoxyphenyl)phosphine]ruthenium(II)

Lei Wang,^a Xiang-Ge Zhou ^a and Rui-Xiang Li ^a ^*

^aKey Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064, People's Republic of China
^*Correspondence e-mail: sculiruixiang@163.com

(Received 18 January 2008; accepted 22 January 2008; online 30 January 2008)

In the title compound, [RuCl₂(C₇H₈)(C₂₁H₂₁O₃P)], the Ru^II atom possesses a pseudo-octahedral geometry and the metrical parameters around the metallic core compare well with those of similar three-legged-piano-stool complexes.

Related literature

For related literature, see: Elsegood & Tocher (1995 ); Hafner et al. (1997 ); Hansen & Nelson (2000 ); Therrien et al. (2004 ); Eapen & Tamborski (1980 ); Winkhaus & Singer (1967 ); Zhang et al. (2006 ).

Experimental

Crystal data

[RuCl₂(C₇H₈)(C₂₁H₂₁O3P)]
M_r = 616.45
Orthorhombic, P n a 2₁
a = 22.1789 (2) Å
b = 8.0564 (1) Å
c = 14.9717 (2) Å
V = 2675.17 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.87 mm⁻¹
T = 296 (2) K
0.24 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.786, T_max = 1.000 (expected range = 0.683–0.869)
20209 measured reflections
5872 independent reflections
4769 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.074
S = 1.01
5872 reflections
320 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.38 e Å⁻³
Absolute structure: Flack (1983 ), 2694 Friedel pairs
Flack parameter: 0.02 (3)

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002341/dn2314sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002341/dn2314Isup2.hkl

checkCIF report

Comment top

Recently, we are interested in the synthesis and catalytic properties of η⁶-arene-ruthenium complexes bearing phosphines (Zhang et al., 2006). These kind of complexes are potential catalysts for many organic reactions, such as hydrogenation of unsaturated organic compound. The title complex was formed in high yield by reacting [RuCl₂(η⁶-C₆H₆)]₂ with tri(4-methoxyphenyl)phosphine in refluxing toluene. In this reaction, the coordinated benzene in ruthenium was replaced by toluene.

In the title compound, the central Ru atom possesses a pseudo-octahedral geometry and is coordinated by two Cl atoms, one P atom of tri(4-methoxyphenyl)phosphine, and three C=C double bonds of toluene (Fig. 1). The metrical parameters around the metallic core compare well with those of similar three-legged piano-stool [Ru(η6-arene)(PPh3)Cl2] complexes (Elsegood & Tocher, 1995; Hafner et al., 1997; Hansen & Nelson, 2000; Therrien et al., 2004).

Related literature top

For related literature, see: Elsegood & Tocher (1995); Hafner et al. (1997); Hansen & Nelson (2000); Therrien et al. (2004); Eapen & Tamborski (1980); Winkhaus & Singer (1967); Zhang et al. (2006).

Experimental top

Synthetic reaction was performed with standard Schlenk technique under nitrogen atmosphere. Solvents were dried over appropriate drying agents and distilled under nitrogen prior to use. [RuCl₂(η⁶-C₆H₆)]₂ and tri(4-methoxyphenyl)phosphine were prepared with the reported methods (Eapen & Tamborski, 1980; Winkhaus & Singer, 1967). A mixture of [RuCl₂(η⁶-C₆H₆)]₂ (0.100 g, 0.20 mmol) and tri(4-methoxyphenyl)phosphine (0.310 g, 0.88 mmol) was refluxed in toluene (50 ml) for 6 h. During refluxing, the solid substances were slowly dissolved and the color of solution changed to crimson. At the end of reaction, the product was obtained as red powder after solvent removal under vacuum. Red crystals of the tittle complex suitable for X-ray structure analysis were obtained by cooling of a dichloromethane-methanol (1:2) solution.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title complex with the atom-labelling scheme. Ellipoids are drawn at the 30% probability level. H atoms have been omitted for clarity.

Dichlorido(η⁶-toluene)[tris(4-methoxyphenyl)phosphine]ruthenium(II) top

Crystal data top

[RuCl₂(C₇H₈)(C₂₁H₂₁O3P)]	F(000) = 1256
M_r = 616.45	D_x = 1.531 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 9291 reflections
a = 22.1789 (2) Å	θ = 2.3–27.4°
b = 8.0564 (1) Å	µ = 0.87 mm⁻¹
c = 14.9717 (2) Å	T = 296 K
V = 2675.17 (5) Å³	Block, red
Z = 4	0.24 × 0.18 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5872 independent reflections
Radiation source: fine-focus sealed tube	4769 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 27.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→28
T_min = 0.786, T_max = 1.000	k = −10→9
20209 measured reflections	l = −19→16

Refinement top

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0336P)² + 0.3363P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.006
5872 reflections	Δρ_max = 0.31 e Å⁻³
320 parameters	Δρ_min = −0.38 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2694 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (3)

Crystal data top

[RuCl₂(C₇H₈)(C₂₁H₂₁O3P)]	V = 2675.17 (5) Å³
M_r = 616.45	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 22.1789 (2) Å	µ = 0.87 mm⁻¹
b = 8.0564 (1) Å	T = 296 K
c = 14.9717 (2) Å	0.24 × 0.18 × 0.16 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5872 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4769 reflections with I > 2σ(I)
T_min = 0.786, T_max = 1.000	R_int = 0.039
20209 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.074	Δρ_max = 0.31 e Å⁻³
S = 1.01	Δρ_min = −0.38 e Å⁻³
5872 reflections	Absolute structure: Flack (1983), 2694 Friedel pairs
320 parameters	Absolute structure parameter: 0.02 (3)
1 restraint

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
Ru1	0.028202 (10)	0.41346 (3)	0.250174 (17)	0.03771 (8)
Cl1	−0.02863 (3)	0.66837 (10)	0.25738 (10)	0.0516 (2)
Cl2	0.02193 (5)	0.39771 (16)	0.41065 (7)	0.0546 (3)
P1	0.11610 (3)	0.57488 (10)	0.26850 (6)	0.0369 (2)
O1	0.33118 (13)	0.1364 (5)	0.3048 (3)	0.0908 (11)
O2	0.16853 (16)	1.0540 (4)	0.5626 (2)	0.0676 (9)
O3	0.16755 (16)	1.0654 (4)	−0.0232 (2)	0.0697 (10)
C1	−0.03640 (19)	0.3238 (5)	0.1463 (3)	0.0566 (11)
C2	−0.03993 (19)	0.2176 (5)	0.2200 (3)	0.0585 (11)
H2	−0.0769	0.1954	0.2468	0.070*
C3	0.01204 (19)	0.1465 (4)	0.2524 (4)	0.0659 (10)
H3	0.0094	0.0774	0.3020	0.079*
C4	0.0672 (2)	0.1728 (6)	0.2150 (4)	0.0718 (14)
H4	0.1011	0.1190	0.2373	0.086*
C5	0.0722 (2)	0.2804 (7)	0.1433 (4)	0.0750 (15)
H5	0.1101	0.3023	0.1193	0.090*
C6	0.0214 (2)	0.3568 (7)	0.1062 (3)	0.0583 (13)
H6	0.0249	0.4268	0.0571	0.070*
C7	−0.0898 (3)	0.4094 (7)	0.1111 (4)	0.0903 (17)
H7A	−0.1088	0.3412	0.0666	0.135*
H7B	−0.0779	0.5130	0.0848	0.135*
H7C	−0.1177	0.4299	0.1589	0.135*
C8	0.18120 (14)	0.4366 (4)	0.2741 (2)	0.0406 (8)
C9	0.18462 (16)	0.3298 (5)	0.3461 (3)	0.0538 (10)
H9	0.1529	0.3272	0.3867	0.065*
C10	0.23391 (16)	0.2258 (5)	0.3599 (3)	0.0554 (11)
H10	0.2358	0.1569	0.4097	0.067*
C11	0.27966 (15)	0.2278 (5)	0.2982 (3)	0.0579 (12)
C12	0.27647 (17)	0.3296 (6)	0.2242 (3)	0.0660 (13)
H12	0.3071	0.3276	0.1817	0.079*
C13	0.22733 (16)	0.4352 (5)	0.2131 (3)	0.0503 (9)
H13	0.2258	0.5054	0.1638	0.060*
C14	0.3391 (2)	0.0338 (6)	0.3805 (4)	0.0813 (15)
H14A	0.3379	0.1005	0.4336	0.122*
H14B	0.3773	−0.0215	0.3767	0.122*
H14C	0.3074	−0.0473	0.3826	0.122*
C15	0.12828 (16)	0.7071 (4)	0.3662 (2)	0.0375 (8)
C16	0.18449 (16)	0.7142 (5)	0.4088 (2)	0.0459 (9)
H16	0.2146	0.6399	0.3924	0.055*
C17	0.19565 (17)	0.8287 (5)	0.4743 (3)	0.0501 (9)
H17	0.2330	0.8305	0.5024	0.060*
C18	0.15195 (19)	0.9417 (5)	0.4989 (3)	0.0478 (10)
C19	0.0950 (2)	0.9340 (5)	0.4593 (3)	0.0510 (11)
H19	0.0648	1.0069	0.4768	0.061*
C20	0.08419 (17)	0.8170 (5)	0.3939 (3)	0.0455 (9)
H20	0.0462	0.8119	0.3678	0.055*
C21	0.1238 (3)	1.1644 (7)	0.5972 (4)	0.0848 (16)
H21A	0.1107	1.2384	0.5508	0.127*
H21B	0.1406	1.2275	0.6455	0.127*
H21C	0.0900	1.1013	0.6185	0.127*
C22	0.13174 (18)	0.7223 (5)	0.1775 (2)	0.0406 (9)
C23	0.18352 (19)	0.8211 (5)	0.1782 (3)	0.0532 (10)
H23	0.2109	0.8122	0.2250	0.064*
C24	0.19421 (19)	0.9319 (5)	0.1096 (3)	0.0576 (10)
H24	0.2294	0.9945	0.1095	0.069*
C25	0.1531 (2)	0.9506 (5)	0.0412 (3)	0.0509 (10)
C26	0.1007 (2)	0.8580 (5)	0.0417 (3)	0.0539 (11)
H26	0.0720	0.8721	−0.0031	0.065*
C27	0.09122 (18)	0.7437 (5)	0.1096 (3)	0.0461 (10)
H27	0.0563	0.6799	0.1089	0.055*
C28	0.1281 (3)	1.0834 (7)	−0.0964 (4)	0.0909 (19)
H28A	0.1224	0.9777	−0.1247	0.136*
H28B	0.1451	1.1602	−0.1385	0.136*
H28C	0.0900	1.1248	−0.0759	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.03768 (12)	0.03808 (13)	0.03737 (14)	0.00240 (10)	0.00388 (15)	−0.00205 (18)
Cl1	0.0416 (3)	0.0481 (4)	0.0652 (6)	0.0107 (3)	−0.0072 (5)	−0.0108 (6)
Cl2	0.0603 (7)	0.0666 (8)	0.0368 (5)	−0.0049 (5)	0.0090 (4)	0.0002 (5)
P1	0.0342 (4)	0.0391 (4)	0.0374 (6)	0.0053 (3)	0.0039 (3)	0.0028 (4)
O1	0.0566 (17)	0.106 (2)	0.110 (3)	0.0447 (17)	0.0301 (17)	0.045 (2)
O2	0.079 (2)	0.068 (2)	0.056 (2)	0.0084 (17)	−0.0140 (16)	−0.0150 (16)
O3	0.085 (2)	0.058 (2)	0.066 (2)	−0.0173 (17)	−0.0039 (17)	0.0198 (17)
C1	0.066 (3)	0.043 (2)	0.060 (2)	0.003 (2)	−0.031 (2)	−0.016 (2)
C2	0.061 (2)	0.049 (2)	0.065 (3)	−0.0174 (19)	0.0051 (19)	−0.006 (2)
C3	0.098 (3)	0.0372 (17)	0.062 (2)	0.0010 (18)	−0.013 (4)	0.003 (3)
C4	0.073 (3)	0.047 (2)	0.095 (4)	0.019 (2)	−0.003 (3)	−0.026 (3)
C5	0.067 (3)	0.079 (4)	0.079 (3)	−0.003 (3)	0.026 (3)	−0.040 (3)
C6	0.086 (4)	0.050 (3)	0.039 (3)	−0.011 (3)	0.002 (2)	−0.006 (2)
C7	0.099 (4)	0.090 (4)	0.081 (4)	−0.020 (3)	−0.013 (3)	0.001 (3)
C8	0.0364 (15)	0.0409 (18)	0.044 (2)	0.0012 (13)	0.0061 (14)	0.0031 (15)
C9	0.044 (2)	0.055 (2)	0.062 (3)	0.0124 (18)	0.0195 (18)	0.016 (2)
C10	0.043 (2)	0.053 (2)	0.070 (3)	0.0092 (18)	0.0145 (18)	0.022 (2)
C11	0.042 (2)	0.055 (3)	0.076 (3)	0.0142 (19)	0.0112 (18)	0.010 (2)
C12	0.046 (2)	0.082 (3)	0.070 (3)	0.020 (2)	0.0230 (19)	0.023 (3)
C13	0.044 (2)	0.061 (2)	0.046 (2)	0.0106 (17)	0.0116 (16)	0.0108 (18)
C14	0.057 (3)	0.070 (3)	0.117 (4)	0.024 (2)	0.012 (3)	0.031 (3)
C15	0.0349 (18)	0.038 (2)	0.0401 (19)	0.0029 (15)	0.0009 (15)	0.0029 (16)
C16	0.0409 (18)	0.054 (2)	0.043 (2)	0.0074 (17)	0.0026 (16)	−0.0038 (18)
C17	0.043 (2)	0.064 (3)	0.043 (2)	0.0007 (19)	−0.0061 (16)	0.001 (2)
C18	0.057 (2)	0.048 (3)	0.038 (2)	0.0019 (19)	−0.0024 (18)	0.0016 (18)
C19	0.054 (2)	0.051 (3)	0.049 (2)	0.014 (2)	−0.0048 (18)	−0.006 (2)
C20	0.0408 (19)	0.048 (2)	0.048 (2)	0.0120 (18)	−0.0079 (17)	−0.0041 (19)
C21	0.111 (4)	0.079 (4)	0.065 (3)	0.027 (4)	−0.015 (3)	−0.023 (3)
C22	0.046 (2)	0.037 (2)	0.039 (2)	0.0029 (17)	0.0057 (16)	0.0002 (16)
C23	0.054 (2)	0.052 (3)	0.054 (2)	−0.003 (2)	−0.0089 (18)	0.0054 (19)
C24	0.053 (2)	0.055 (2)	0.064 (3)	−0.011 (2)	0.004 (2)	0.009 (2)
C25	0.069 (3)	0.038 (2)	0.045 (2)	−0.005 (2)	0.006 (2)	0.0030 (19)
C26	0.061 (3)	0.049 (3)	0.052 (2)	−0.002 (2)	−0.007 (2)	0.006 (2)
C27	0.045 (2)	0.045 (2)	0.049 (2)	−0.0058 (18)	0.0004 (17)	0.0055 (19)
C28	0.132 (5)	0.080 (4)	0.061 (3)	−0.025 (4)	−0.023 (3)	0.026 (3)

Geometric parameters (Å, º) top

Ru1—C5	2.160 (4)	C9—H9	0.9300
Ru1—C3	2.181 (3)	C10—C11	1.372 (5)
Ru1—C4	2.188 (4)	C10—H10	0.9300
Ru1—C6	2.208 (5)	C11—C12	1.382 (5)
Ru1—C2	2.231 (4)	C12—C13	1.392 (5)
Ru1—C1	2.235 (4)	C12—H12	0.9300
Ru1—P1	2.3593 (8)	C13—H13	0.9300
Ru1—Cl2	2.4099 (12)	C14—H14A	0.9600
Ru1—Cl1	2.4121 (8)	C14—H14B	0.9600
P1—C8	1.826 (3)	C14—H14C	0.9600
P1—C15	1.830 (4)	C15—C20	1.382 (5)
P1—C22	1.841 (4)	C15—C16	1.402 (5)
O1—C11	1.363 (4)	C16—C17	1.369 (5)
O1—C14	1.414 (6)	C16—H16	0.9300
O2—C18	1.365 (5)	C17—C18	1.380 (6)
O2—C21	1.429 (6)	C17—H17	0.9300
O3—C25	1.373 (5)	C18—C19	1.396 (6)
O3—C28	1.410 (6)	C19—C20	1.380 (6)
C1—C2	1.399 (6)	C19—H19	0.9300
C1—C6	1.441 (7)	C20—H20	0.9300
C1—C7	1.469 (6)	C21—H21A	0.9600
C2—C3	1.375 (6)	C21—H21B	0.9600
C2—H2	0.9300	C21—H21C	0.9600
C3—C4	1.362 (6)	C22—C27	1.367 (5)
C3—H3	0.9300	C22—C23	1.397 (6)
C4—C5	1.385 (7)	C23—C24	1.381 (6)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.399 (7)	C24—C25	1.380 (6)
C5—H5	0.9300	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.381 (6)
C7—H7A	0.9600	C26—C27	1.388 (6)
C7—H7B	0.9600	C26—H26	0.9300
C7—H7C	0.9600	C27—H27	0.9300
C8—C13	1.372 (4)	C28—H28A	0.9600
C8—C9	1.381 (5)	C28—H28B	0.9600
C9—C10	1.393 (5)	C28—H28C	0.9600

C5—Ru1—C3	66.2 (2)	Ru1—C6—H6	129.8
C5—Ru1—C4	37.14 (19)	C1—C7—H7A	109.5
C3—Ru1—C4	36.33 (18)	C1—C7—H7B	109.5
C5—Ru1—C6	37.33 (19)	H7A—C7—H7B	109.5
C3—Ru1—C6	78.4 (2)	C1—C7—H7C	109.5
C4—Ru1—C6	66.9 (2)	H7A—C7—H7C	109.5
C5—Ru1—C2	78.77 (17)	H7B—C7—H7C	109.5
C3—Ru1—C2	36.30 (15)	C13—C8—C9	118.3 (3)
C4—Ru1—C2	65.93 (17)	C13—C8—P1	124.4 (3)
C6—Ru1—C2	67.05 (17)	C9—C8—P1	117.4 (2)
C5—Ru1—C1	67.28 (18)	C8—C9—C10	122.3 (3)
C3—Ru1—C1	65.56 (18)	C8—C9—H9	118.9
C4—Ru1—C1	78.42 (16)	C10—C9—H9	118.9
C6—Ru1—C1	37.83 (17)	C11—C10—C9	118.2 (4)
C2—Ru1—C1	36.51 (16)	C11—C10—H10	120.9
C5—Ru1—P1	89.21 (13)	C9—C10—H10	120.9
C3—Ru1—P1	132.66 (11)	O1—C11—C10	124.4 (4)
C4—Ru1—P1	100.95 (13)	O1—C11—C12	114.9 (4)
C6—Ru1—P1	106.49 (14)	C10—C11—C12	120.6 (3)
C2—Ru1—P1	166.66 (11)	C11—C12—C13	119.9 (3)
C1—Ru1—P1	142.09 (13)	C11—C12—H12	120.1
C5—Ru1—Cl2	137.63 (17)	C13—C12—H12	120.1
C3—Ru1—Cl2	85.62 (18)	C8—C13—C12	120.6 (4)
C4—Ru1—Cl2	102.49 (15)	C8—C13—H13	119.7
C6—Ru1—Cl2	163.37 (14)	C12—C13—H13	119.7
C2—Ru1—Cl2	97.20 (11)	O1—C14—H14A	109.5
C1—Ru1—Cl2	129.78 (13)	O1—C14—H14B	109.5
P1—Ru1—Cl2	87.75 (4)	H14A—C14—H14B	109.5
C5—Ru1—Cl1	133.79 (17)	O1—C14—H14C	109.5
C3—Ru1—Cl1	138.86 (12)	H14A—C14—H14C	109.5
C4—Ru1—Cl1	166.42 (13)	H14B—C14—H14C	109.5
C6—Ru1—Cl1	100.61 (15)	C20—C15—C16	117.8 (3)
C2—Ru1—Cl1	104.91 (11)	C20—C15—P1	120.5 (3)
C1—Ru1—Cl1	88.35 (11)	C16—C15—P1	121.3 (3)
P1—Ru1—Cl1	87.55 (3)	C17—C16—C15	120.9 (3)
Cl2—Ru1—Cl1	88.29 (5)	C17—C16—H16	119.5
C8—P1—C15	101.64 (15)	C15—C16—H16	119.5
C8—P1—C22	106.18 (16)	C16—C17—C18	120.6 (4)
C15—P1—C22	100.85 (16)	C16—C17—H17	119.7
C8—P1—Ru1	108.81 (11)	C18—C17—H17	119.7
C15—P1—Ru1	122.41 (12)	O2—C18—C17	115.8 (4)
C22—P1—Ru1	115.17 (13)	O2—C18—C19	124.8 (4)
C11—O1—C14	118.5 (3)	C17—C18—C19	119.5 (4)
C18—O2—C21	118.6 (4)	C20—C19—C18	119.3 (4)
C25—O3—C28	118.0 (4)	C20—C19—H19	120.3
C2—C1—C6	119.4 (4)	C18—C19—H19	120.3
C2—C1—C7	121.7 (4)	C19—C20—C15	121.8 (4)
C6—C1—C7	118.8 (5)	C19—C20—H20	119.1
C2—C1—Ru1	71.6 (2)	C15—C20—H20	119.1
C6—C1—Ru1	70.1 (2)	O2—C21—H21A	109.5
C7—C1—Ru1	128.0 (3)	O2—C21—H21B	109.5
C3—C2—C1	119.1 (4)	H21A—C21—H21B	109.5
C3—C2—Ru1	69.9 (2)	O2—C21—H21C	109.5
C1—C2—Ru1	71.9 (2)	H21A—C21—H21C	109.5
C3—C2—H2	120.5	H21B—C21—H21C	109.5
C1—C2—H2	120.5	C27—C22—C23	118.3 (4)
Ru1—C2—H2	130.2	C27—C22—P1	120.5 (3)
C4—C3—C2	122.9 (5)	C23—C22—P1	121.1 (3)
C4—C3—Ru1	72.1 (2)	C24—C23—C22	120.2 (4)
C2—C3—Ru1	73.8 (2)	C24—C23—H23	119.9
C4—C3—H3	118.5	C22—C23—H23	119.9
C2—C3—H3	118.5	C25—C24—C23	120.6 (4)
Ru1—C3—H3	127.8	C25—C24—H24	119.7
C3—C4—C5	119.2 (4)	C23—C24—H24	119.7
C3—C4—Ru1	71.5 (2)	O3—C25—C24	116.1 (4)
C5—C4—Ru1	70.3 (3)	O3—C25—C26	124.3 (4)
C3—C4—H4	120.4	C24—C25—C26	119.6 (4)
C5—C4—H4	120.4	C25—C26—C27	119.3 (4)
Ru1—C4—H4	130.2	C25—C26—H26	120.3
C4—C5—C6	121.2 (4)	C27—C26—H26	120.3
C4—C5—Ru1	72.5 (3)	C22—C27—C26	121.9 (4)
C6—C5—Ru1	73.2 (3)	C22—C27—H27	119.0
C4—C5—H5	119.4	C26—C27—H27	119.0
C6—C5—H5	119.4	O3—C28—H28A	109.5
Ru1—C5—H5	126.9	O3—C28—H28B	109.5
C5—C6—C1	118.1 (5)	H28A—C28—H28B	109.5
C5—C6—Ru1	69.5 (3)	O3—C28—H28C	109.5
C1—C6—Ru1	72.1 (3)	H28A—C28—H28C	109.5
C5—C6—H6	120.9	H28B—C28—H28C	109.5
C1—C6—H6	120.9

Experimental details

Crystal data
Chemical formula	[RuCl₂(C₇H₈)(C₂₁H₂₁O3P)]
M_r	616.45
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	22.1789 (2), 8.0564 (1), 14.9717 (2)
V (Å³)	2675.17 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.87
Crystal size (mm)	0.24 × 0.18 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.786, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	20209, 5872, 4769
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.074, 1.01
No. of reflections	5872
No. of parameters	320
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.38
Absolute structure	Flack (1983), 2694 Friedel pairs
Absolute structure parameter	0.02 (3)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

Financial support for this work by the National Science Foundation of China (Nos. 20371032 and 20271035) is gratefully acknowledged.

References

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