Dichloridobis[(1S,1S′,2R,2R′)-(+)-1,1′-di-tert-butyl-2,2′-diphospho­lane-κ2P,P′]ruthenium(II)

Wang, C.; Tao, H.; Ji, B.

doi:10.1107/S1600536808008301

metal-organic compounds

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Volume 64| Part 6| June 2008| Page m754

doi:10.1107/S1600536808008301

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Dichloridobis[(1S,1S′,2R,2R′)-(+)-1,1′-di-tert-butyl-2,2′-diphospholane-κ²P,P′]ruthenium(II)

Chubei Wang,^a Haiyan Tao ^b ^* and Baoming Ji ^c

^aCollege of Chemistry, Central China Normal University, Wuhan, Hubei 430072, People's Republic of China, ^bCollege of Chemistry and Molecular Science, Wuhan University, Wuhan, Hubei 430072, People's Republic of China, and ^cCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, Henan 471022, People's Republic of China
^*Correspondence e-mail: haiyantao21@hotmail.com

(Received 29 February 2008; accepted 27 March 2008; online 3 May 2008)

In the title compound, [RuCl₂(C₁₆H₃₂P₂)₂], the Ru^II ion is situated on a twofold rotation axis, so the asymmetric unit contains one half-molecule. The slightly distorted octahedral environment of the Ru center is formed by four P atoms [Ru—P = 2.4417 (6) and 2.4544 (6) Å] from two different (1S,1S′,2R,2R′)-TangPhos ligands [(1S,1S′,2R,2R′)-TangPhos = (1S,1S′,2R,2R′)-(+)-1,1′-di-tert-butyl-2,2′-diphospholane] and two Cl atoms [Ru—Cl = 2.4267 (5) Å].

Related literature

For related literature, see: Ikariya et al. (1985 ); James & Fogg (1993 ); Stoop et al. (1999 ).

Experimental

Crystal data

[RuCl₂(C₁₆H₃₂P₂)₂]
M_r = 744.72
Orthorhombic, C 222₁
a = 11.8640 (14) Å
b = 20.669 (3) Å
c = 14.2274 (17) Å
V = 3488.8 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 108 (2) K
0.24 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.863, T_max = 0.921
11542 measured reflections
4164 independent reflections
4018 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.057
S = 1.06
4164 reflections
183 parameters
H-atom parameters not refined
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1750 Friedel pairs
Flack parameter: 0.00 (2)

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008301/cv2390sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008301/cv2390Isup2.hkl

checkCIF report

Comment top

Recently, some chiral diphosphino ruthenium complexes have been synthesized and used as catalysts for the asymmetric reactions (Stoop et al., 1999; James et al., 1993). Herein, we report the synthesis and crystal structure of the title compound - the ruthenium(II) complex containing the chiral TangPhos ligand.

As shown in Fig. 1, the crystals of the title complex contain discrete [RuCl₂(TangPhos)₂] units with the metal center in a slightly distorted octahedral environment. The trans-axial positions of Ru^II environment are occupied by Cl1 and Cl1ⁱ atoms, and the equatorial positions are occupied by P1, P2, P1ⁱ, P2ⁱ atoms, respectively [symmetry code: (i) -x, y, -z + 1/2], from two different TangPhos ligands, resulting in two chelate rings, which assume a half-chair conformation with the tert-butyl in the less hindered equatorial positions. Similar conformations were found in previously reported related structures (Stoop et al., 1999; Ikariya et al., 1985).

Related literature top

For related literature, see: Ikariya et al. (1985); James & Fogg (1993); Stoop et al. (1999).

Experimental top

To a solution of [RuCl₂(PPh)₃] (96 mg, 0.1 mmol) in 2 ml of deoxygenated CH₂Cl₂ was added dropwise a solution of (1S,1S',2R,2R')-TangPhos, (56 mg, 0.2 mmol) in CH₂Cl₂ (1 ml). The resulting mixture was stirred at ambient temperature for 6 h. Deoxygenated ether (12 ml) was added into the vigorously stirring solution and kept for 6 h at room temperature. The resulting light brown precipitate was filtered, washed with ether (3 times with 10 ml), and dried under vacuum. Yield: 45 mg (56%). Crystals suitable for X-ray diffraction were obtained by diffusion of hexane into a CD₂Cl₂ solution of the above compound at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound with the atomic numbering and 40% probability displacement ellipsoids [symmetry code: (i) -x, y, -z + 1/2]. H atoms are omitted for clarity.

Dichloridobis[(1S,1S',2R,2R')-(+)-1,1'-di-tert-butyl-2,2'- diphospholane-κ²P,P']ruthenium(II) top

Crystal data top

[RuCl₂(C₁₆H₃₂P₂)₂]	F(000) = 1576
M_r = 744.72	D_x = 1.418 Mg m⁻³
Orthorhombic, C222₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 5992 reflections
a = 11.8640 (14) Å	θ = 2.4–28.2°
b = 20.669 (3) Å	µ = 0.81 mm⁻¹
c = 14.2274 (17) Å	T = 108 K
V = 3488.8 (8) Å³	Brick, orange
Z = 4	0.24 × 0.15 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4164 independent reflections
Radiation source: fine-focus sealed tube	4018 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
phi and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→15
T_min = 0.863, T_max = 0.921	k = −17→27
11542 measured reflections	l = −18→18

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)] = 0.024	H-atom parameters not refined
wR(F²) = 0.057	w = 1/[σ²(F_o²) + (0.0315P)² + 0.2939P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.003
4164 reflections	Δρ_max = 0.83 e Å⁻³
183 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1750 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (2)

Crystal data top

[RuCl₂(C₁₆H₃₂P₂)₂]	V = 3488.8 (8) Å³
M_r = 744.72	Z = 4
Orthorhombic, C222₁	Mo Kα radiation
a = 11.8640 (14) Å	µ = 0.81 mm⁻¹
b = 20.669 (3) Å	T = 108 K
c = 14.2274 (17) Å	0.24 × 0.15 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4164 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4018 reflections with I > 2σ(I)
T_min = 0.863, T_max = 0.921	R_int = 0.025
11542 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	H-atom parameters not refined
wR(F²) = 0.057	Δρ_max = 0.83 e Å⁻³
S = 1.06	Δρ_min = −0.29 e Å⁻³
4164 reflections	Absolute structure: Flack (1983), 1750 Friedel pairs
183 parameters	Absolute structure parameter: 0.00 (2)
0 restraints

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	0.02414 (19)	0.16346 (11)	−0.00952 (15)	0.0256 (5)
H1A	−0.0059	0.1290	−0.0497	0.038*
H1B	0.0806	0.1883	−0.0445	0.038*
H1C	−0.0373	0.1922	0.0098	0.038*
C2	−0.0038 (3)	0.08613 (11)	0.12059 (16)	0.0353 (6)
H2A	−0.0740	0.1086	0.1364	0.053*
H2B	0.0291	0.0677	0.1778	0.053*
H2C	−0.0198	0.0514	0.0756	0.053*
C3	0.1820 (2)	0.09489 (11)	0.04344 (16)	0.0257 (5)
H3A	0.2177	0.0737	0.0973	0.039*
H3B	0.2361	0.1243	0.0136	0.039*
H3C	0.1580	0.0621	−0.0021	0.039*
C4	0.07852 (18)	0.13369 (11)	0.07717 (15)	0.0188 (4)
C5	0.21860 (15)	0.15194 (10)	0.24348 (17)	0.0185 (4)
H5A	0.2097	0.1649	0.3100	0.022*
H5B	0.2031	0.1050	0.2384	0.022*
C6	0.33823 (17)	0.16652 (12)	0.21003 (18)	0.0262 (5)
H6A	0.3927	0.1616	0.2622	0.031*
H6B	0.3601	0.1369	0.1584	0.031*
C7	0.33514 (17)	0.23639 (12)	0.17560 (17)	0.0261 (5)
H7A	0.4066	0.2474	0.1434	0.031*
H7B	0.3250	0.2663	0.2293	0.031*
C8	0.23545 (18)	0.24229 (10)	0.10707 (15)	0.0179 (4)
H8	0.2549	0.2176	0.0489	0.021*
C9	0.20454 (18)	0.31083 (11)	0.07802 (15)	0.0185 (4)
H9	0.2760	0.3358	0.0695	0.022*
C10	0.13653 (19)	0.31551 (11)	−0.01378 (14)	0.0220 (5)
H10A	0.1839	0.3027	−0.0680	0.026*
H10B	0.0702	0.2865	−0.0112	0.026*
C11	0.09906 (19)	0.38550 (11)	−0.02376 (15)	0.0237 (5)
H11A	0.0465	0.3904	−0.0773	0.028*
H11B	0.1647	0.4142	−0.0338	0.028*
C12	0.04012 (19)	0.40157 (10)	0.06914 (15)	0.0203 (5)
H12A	−0.0402	0.3887	0.0663	0.024*
H12B	0.0442	0.4486	0.0817	0.024*
C13	0.2153 (2)	0.42001 (11)	0.21194 (17)	0.0261 (5)
C14	0.3123 (2)	0.39022 (14)	0.26745 (19)	0.0414 (7)
H14A	0.3582	0.4247	0.2951	0.062*
H14B	0.3590	0.3640	0.2253	0.062*
H14C	0.2819	0.3628	0.3176	0.062*
C15	0.2678 (2)	0.46048 (11)	0.13264 (17)	0.0291 (5)
H15A	0.2078	0.4806	0.0954	0.044*
H15B	0.3134	0.4324	0.0921	0.044*
H15C	0.3158	0.4943	0.1598	0.044*
C16	0.1502 (3)	0.46594 (13)	0.2754 (2)	0.0505 (9)
H16A	0.1180	0.4417	0.3281	0.076*
H16B	0.0895	0.4864	0.2394	0.076*
H16C	0.2013	0.4993	0.2995	0.076*
Cl1	−0.13351 (4)	0.27771 (3)	0.12078 (3)	0.01700 (10)
P1	0.11419 (5)	0.35562 (3)	0.16379 (4)	0.01581 (11)
P2	0.11916 (4)	0.19819 (3)	0.16823 (4)	0.01347 (11)
Ru1	0.0000	0.277275 (10)	0.2500	0.01108 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0294 (13)	0.0265 (11)	0.0207 (11)	0.0048 (10)	−0.0060 (9)	−0.0074 (9)
C2	0.0464 (14)	0.0316 (12)	0.0279 (12)	−0.0175 (14)	0.0162 (14)	−0.0125 (10)
C3	0.0352 (13)	0.0209 (11)	0.0209 (11)	0.0099 (10)	0.0033 (10)	−0.0011 (9)
C4	0.0241 (11)	0.0182 (10)	0.0142 (10)	0.0018 (9)	0.0029 (8)	−0.0020 (8)
C5	0.0201 (10)	0.0212 (9)	0.0141 (9)	0.0048 (8)	0.0021 (9)	0.0025 (10)
C6	0.0168 (11)	0.0359 (14)	0.0260 (11)	0.0088 (10)	0.0036 (9)	0.0107 (10)
C7	0.0132 (10)	0.0342 (15)	0.0310 (12)	−0.0006 (9)	0.0012 (9)	0.0117 (10)
C8	0.0166 (10)	0.0211 (11)	0.0159 (9)	0.0012 (8)	0.0046 (8)	0.0031 (8)
C9	0.0181 (10)	0.0208 (11)	0.0166 (10)	0.0011 (8)	0.0045 (8)	0.0041 (9)
C10	0.0285 (12)	0.0242 (12)	0.0133 (10)	0.0052 (10)	0.0058 (9)	0.0023 (8)
C11	0.0304 (13)	0.0240 (12)	0.0166 (11)	0.0015 (10)	0.0039 (9)	0.0061 (9)
C12	0.0247 (11)	0.0162 (10)	0.0199 (11)	0.0009 (9)	0.0015 (8)	0.0037 (9)
C13	0.0326 (13)	0.0224 (12)	0.0234 (11)	−0.0126 (10)	0.0024 (10)	−0.0004 (10)
C14	0.0485 (16)	0.0439 (15)	0.0317 (17)	−0.0285 (13)	−0.0166 (12)	0.0120 (12)
C15	0.0348 (13)	0.0212 (11)	0.0315 (13)	−0.0111 (11)	0.0056 (11)	0.0024 (10)
C16	0.0582 (19)	0.0429 (17)	0.050 (2)	−0.0304 (15)	0.0255 (15)	−0.0289 (14)
Cl1	0.0168 (2)	0.0205 (2)	0.0137 (2)	0.0003 (2)	−0.00355 (16)	0.0000 (2)
P1	0.0188 (3)	0.0144 (3)	0.0143 (3)	−0.0034 (2)	0.0013 (2)	0.0013 (2)
P2	0.0146 (3)	0.0147 (2)	0.0111 (2)	0.0011 (2)	0.0020 (2)	0.0013 (2)
Ru1	0.01224 (10)	0.01165 (10)	0.00935 (9)	0.000	0.00015 (8)	0.000

Geometric parameters (Å, º) top

C1—C4	1.522 (3)	C10—C11	1.520 (3)
C1—H1A	0.9800	C10—H10A	0.9900
C1—H1B	0.9800	C10—H10B	0.9900
C1—H1C	0.9800	C11—C12	1.532 (3)
C2—C4	1.517 (3)	C11—H11A	0.9900
C2—H2A	0.9800	C11—H11B	0.9900
C2—H2B	0.9800	C12—P1	1.868 (2)
C2—H2C	0.9800	C12—H12A	0.9900
C3—C4	1.543 (3)	C12—H12B	0.9900
C3—H3A	0.9800	C13—C16	1.520 (4)
C3—H3B	0.9800	C13—C14	1.525 (3)
C3—H3C	0.9800	C13—C15	1.537 (3)
C4—P2	1.920 (2)	C13—P1	1.918 (2)
C5—C6	1.527 (3)	C14—H14A	0.9800
C5—P2	1.858 (2)	C14—H14B	0.9800
C5—H5A	0.9900	C14—H14C	0.9800
C5—H5B	0.9900	C15—H15A	0.9800
C6—C7	1.525 (3)	C15—H15B	0.9800
C6—H6A	0.9900	C15—H15C	0.9800
C6—H6B	0.9900	C16—H16A	0.9800
C7—C8	1.538 (3)	C16—H16B	0.9800
C7—H7A	0.9900	C16—H16C	0.9800
C7—H7B	0.9900	Cl1—Ru1	2.4267 (5)
C8—C9	1.521 (3)	P1—Ru1	2.4417 (6)
C8—P2	1.869 (2)	P2—Ru1	2.4544 (6)
C8—H8	1.0000	Ru1—Cl1ⁱ	2.4267 (5)
C9—C10	1.538 (3)	Ru1—P1ⁱ	2.4417 (6)
C9—P1	1.870 (2)	Ru1—P2ⁱ	2.4544 (6)
C9—H9	1.0000

C4—C1—H1A	109.5	C12—C11—H11A	110.7
C4—C1—H1B	109.5	C10—C11—H11B	110.7
H1A—C1—H1B	109.5	C12—C11—H11B	110.7
C4—C1—H1C	109.5	H11A—C11—H11B	108.8
H1A—C1—H1C	109.5	C11—C12—P1	107.29 (15)
H1B—C1—H1C	109.5	C11—C12—H12A	110.3
C4—C2—H2A	109.5	P1—C12—H12A	110.3
C4—C2—H2B	109.5	C11—C12—H12B	110.3
H2A—C2—H2B	109.5	P1—C12—H12B	110.3
C4—C2—H2C	109.5	H12A—C12—H12B	108.5
H2A—C2—H2C	109.5	C16—C13—C14	109.1 (2)
H2B—C2—H2C	109.5	C16—C13—C15	107.6 (2)
C4—C3—H3A	109.5	C14—C13—C15	107.1 (2)
C4—C3—H3B	109.5	C16—C13—P1	109.12 (17)
H3A—C3—H3B	109.5	C14—C13—P1	112.12 (17)
C4—C3—H3C	109.5	C15—C13—P1	111.66 (16)
H3A—C3—H3C	109.5	C13—C14—H14A	109.5
H3B—C3—H3C	109.5	C13—C14—H14B	109.5
C2—C4—C1	108.6 (2)	H14A—C14—H14B	109.5
C2—C4—C3	107.60 (19)	C13—C14—H14C	109.5
C1—C4—C3	107.18 (17)	H14A—C14—H14C	109.5
C2—C4—P2	109.67 (14)	H14B—C14—H14C	109.5
C1—C4—P2	111.87 (15)	C13—C15—H15A	109.5
C3—C4—P2	111.76 (15)	C13—C15—H15B	109.5
C6—C5—P2	108.00 (15)	H15A—C15—H15B	109.5
C6—C5—H5A	110.1	C13—C15—H15C	109.5
P2—C5—H5A	110.1	H15A—C15—H15C	109.5
C6—C5—H5B	110.1	H15B—C15—H15C	109.5
P2—C5—H5B	110.1	C13—C16—H16A	109.5
H5A—C5—H5B	108.4	C13—C16—H16B	109.5
C7—C6—C5	105.35 (17)	H16A—C16—H16B	109.5
C7—C6—H6A	110.7	C13—C16—H16C	109.5
C5—C6—H6A	110.7	H16A—C16—H16C	109.5
C7—C6—H6B	110.7	H16B—C16—H16C	109.5
C5—C6—H6B	110.7	C12—P1—C9	92.92 (10)
H6A—C6—H6B	108.8	C12—P1—C13	101.48 (10)
C6—C7—C8	107.28 (19)	C9—P1—C13	102.59 (10)
C6—C7—H7A	110.3	C12—P1—Ru1	116.00 (7)
C8—C7—H7A	110.3	C9—P1—Ru1	108.52 (7)
C6—C7—H7B	110.3	C13—P1—Ru1	128.89 (8)
C8—C7—H7B	110.3	C5—P2—C8	92.89 (9)
H7A—C7—H7B	108.5	C5—P2—C4	101.01 (10)
C9—C8—C7	115.57 (18)	C8—P2—C4	102.11 (9)
C9—C8—P2	113.76 (15)	C5—P2—Ru1	115.80 (8)
C7—C8—P2	103.53 (14)	C8—P2—Ru1	108.73 (7)
C9—C8—H8	107.9	C4—P2—Ru1	129.60 (7)
C7—C8—H8	107.9	Cl1ⁱ—Ru1—Cl1	179.58 (3)
P2—C8—H8	107.9	Cl1ⁱ—Ru1—P1	90.913 (19)
C8—C9—C10	114.56 (18)	Cl1—Ru1—P1	88.806 (19)
C8—C9—P1	114.98 (15)	Cl1ⁱ—Ru1—P1ⁱ	88.806 (19)
C10—C9—P1	102.85 (14)	Cl1—Ru1—P1ⁱ	90.913 (19)
C8—C9—H9	108.0	P1—Ru1—P1ⁱ	96.91 (3)
C10—C9—H9	108.0	Cl1ⁱ—Ru1—P2ⁱ	91.107 (19)
P1—C9—H9	108.0	Cl1—Ru1—P2ⁱ	89.175 (19)
C11—C10—C9	107.00 (18)	P1—Ru1—P2ⁱ	177.969 (19)
C11—C10—H10A	110.3	P1ⁱ—Ru1—P2ⁱ	83.341 (18)
C9—C10—H10A	110.3	Cl1ⁱ—Ru1—P2	89.175 (19)
C11—C10—H10B	110.3	Cl1—Ru1—P2	91.107 (19)
C9—C10—H10B	110.3	P1—Ru1—P2	83.341 (18)
H10A—C10—H10B	108.6	P1ⁱ—Ru1—P2	177.969 (19)
C10—C11—C12	105.02 (17)	P2ⁱ—Ru1—P2	96.48 (3)
C10—C11—H11A	110.7

P2—C5—C6—C7	33.0 (2)	C9—C8—P2—C4	110.84 (16)
C5—C6—C7—C8	−50.9 (2)	C7—C8—P2—C4	−122.93 (15)
C6—C7—C8—C9	169.48 (18)	C9—C8—P2—Ru1	−28.74 (16)
C6—C7—C8—P2	44.4 (2)	C7—C8—P2—Ru1	97.50 (14)
C7—C8—C9—C10	159.29 (18)	C2—C4—P2—C5	76.02 (19)
P2—C8—C9—C10	−81.1 (2)	C1—C4—P2—C5	−163.42 (15)
C7—C8—C9—P1	−81.9 (2)	C3—C4—P2—C5	−43.22 (17)
P2—C8—C9—P1	37.76 (19)	C2—C4—P2—C8	171.43 (17)
C8—C9—C10—C11	171.88 (18)	C1—C4—P2—C8	−68.01 (17)
P1—C9—C10—C11	46.39 (19)	C3—C4—P2—C8	52.19 (17)
C9—C10—C11—C12	−53.0 (2)	C2—C4—P2—Ru1	−61.4 (2)
C10—C11—C12—P1	33.8 (2)	C1—C4—P2—Ru1	59.14 (18)
C11—C12—P1—C9	−6.50 (16)	C3—C4—P2—Ru1	179.34 (11)
C11—C12—P1—C13	96.98 (16)	C12—P1—Ru1—Cl1ⁱ	−160.02 (8)
C11—C12—P1—Ru1	−118.75 (14)	C9—P1—Ru1—Cl1ⁱ	97.09 (7)
C8—C9—P1—C12	−147.28 (16)	C13—P1—Ru1—Cl1ⁱ	−27.34 (10)
C10—C9—P1—C12	−22.07 (15)	C12—P1—Ru1—Cl1	19.66 (8)
C8—C9—P1—C13	110.27 (16)	C9—P1—Ru1—Cl1	−83.23 (7)
C10—C9—P1—C13	−124.52 (15)	C13—P1—Ru1—Cl1	152.34 (10)
C8—C9—P1—Ru1	−28.60 (16)	C12—P1—Ru1—P1ⁱ	−71.11 (8)
C10—C9—P1—Ru1	96.61 (13)	C9—P1—Ru1—P1ⁱ	−174.00 (8)
C16—C13—P1—C12	77.9 (2)	C13—P1—Ru1—P1ⁱ	61.56 (10)
C14—C13—P1—C12	−161.05 (17)	C12—P1—Ru1—P2	110.92 (8)
C15—C13—P1—C12	−40.84 (19)	C9—P1—Ru1—P2	8.03 (7)
C16—C13—P1—C9	173.58 (18)	C13—P1—Ru1—P2	−116.41 (10)
C14—C13—P1—C9	−65.40 (19)	C5—P2—Ru1—Cl1ⁱ	20.56 (7)
C15—C13—P1—C9	54.81 (19)	C8—P2—Ru1—Cl1ⁱ	−82.33 (7)
C16—C13—P1—Ru1	−59.7 (2)	C4—P2—Ru1—Cl1ⁱ	153.05 (9)
C14—C13—P1—Ru1	61.3 (2)	C5—P2—Ru1—Cl1	−159.76 (7)
C15—C13—P1—Ru1	−178.44 (13)	C8—P2—Ru1—Cl1	97.35 (7)
C6—C5—P2—C8	−6.72 (17)	C4—P2—Ru1—Cl1	−27.27 (9)
C6—C5—P2—C4	96.21 (17)	C8—P2—Ru1—P1	8.68 (7)
C6—C5—P2—Ru1	−119.15 (15)	C5—P2—Ru1—P2ⁱ	−70.46 (7)
C9—C8—P2—C5	−147.25 (16)	C8—P2—Ru1—P2ⁱ	−173.36 (8)
C7—C8—P2—C5	−21.02 (16)	C4—P2—Ru1—P2ⁱ	62.03 (9)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[RuCl₂(C₁₆H₃₂P₂)₂]
M_r	744.72
Crystal system, space group	Orthorhombic, C222₁
Temperature (K)	108
a, b, c (Å)	11.8640 (14), 20.669 (3), 14.2274 (17)
V (Å³)	3488.8 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.24 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.863, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	11542, 4164, 4018
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.057, 1.06
No. of reflections	4164
No. of parameters	183
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.29
Absolute structure	Flack (1983), 1750 Friedel pairs
Absolute structure parameter	0.00 (2)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 20702039).

References

Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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