(η6-Benzene)­dichlorido­(chloro­dicyclo­hexyl­phosphane-κP)ruthenium(II) chloro­form monosolvate

Gowrisankar, S.; Neumann, H.; Spannenberg, A.; Beller, M.

doi:10.1107/S1600536814012975

(η⁶-Benzene)dichlorido(chlorodicyclohexylphosphane-κP)ruthenium(II) chloroform monosolvate

S. Gowrisankar, H. Neumann, A. Spannenberg and M. Beller

The title compound, [RuCl₂(η⁶-C₆H₆)(C₁₂H₂₂ClP)]·CHCl₃, was prepared by reaction of [RuCl₂(η⁶-C₆H₆)]₂ with chlorodicyclohexylphosphane in CHCl₃ at 323 K under argon. The Ru^II atom is surrounded by one arene ligand, two Cl atoms and a phosphane ligand in a piano-stool geometry. The phosphane ligand is linked by the P atom, with an Ru—P bond length of 2.3247 (4) Å. Both cyclohexyl rings at the P atom adopt a chair conformation. In the crystal, the Ru^II complex molecule and the chloroform solvent molecule are linked by a bifurcated C—H

(Cl,Cl) hydrogen bond. Intramolecular C—H

Cl hydrogen bonds are also observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536814012975/is5363sup1.cif Contains datablocks I, Global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536814012975/is5363Isup2.hkl Contains datablock I

CCDC reference: 1006720

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R factor = 0.019
wR factor = 0.048
Data-to-parameter ratio = 23.0

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ru1    --  Cl1     ..        8.0 su
PLAT434_ALERT_2_G Short Inter HL..HL Contact  Cl2    ..  Cl4     .       3.36 Ang.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The half-sandwich (η⁶–C₆H₆)-dichlorido(chlorodicyclohexylphosphane)ruthenium(II) complex was formed by reaction of one equivalent of [RuCl₂(η⁶-C₆H₆)]₂ with two equivalents of (Cy₂P(1-naphthoyl)) ligand under hydrogenation conditions (CHCl₃, 60 bar of H₂, 353 K, 3 hrs) as a side product. The cleavage of the 1-naphthoyl group from [RuCl₂(η⁶-C₆H₆)(Cy₂P(1-naphthoyl)] complex forms firstly [RuCl₂(η⁶-C₆H₆)(Cy₂PH)] and subsequent chlorination of the dicyclohexylphosphane unit due to CHCl₃ yields the title compound in poor yield. Additionally, we could not observe any trace amount of title compound by using non-chlorinated solvents such as MeOH. The substitution of hydrogen next to phosphane by chlorine coming from solvent molecules is also described for the formation of a Ru-complex with the related chlorodiphenylphosphane ligand by Torres-Lubián et al. (1999). More specifically, the title complex was formed by reaction of [RuCl₂(η⁶-C₆H₆)]₂ with chlorodicyclohexylphosphane in CHCl₃ at 323 K under argon in 41% yield. Crystals suitable for X-ray crystal structure analysis could be obtained by crystallization from a chloroform/heptane mixture. In the ³¹P NMR spectrum of the complex the signal for the phosphorus was observed at 156.3 p.p.m., whereas free ligand signal appears at 128.8 p.p.m.. The title compound shows the three legged piano-stool geometry at the ruthenium centre with the arene, chlorodicyclohexylphosphane and two chlorine ligands in the coordination sphere (Fig. 1). The phosphane ligand is linked by the phosphorus with a Ru—P bond length of 2.3247 (4) Å. Both cyclohexyl rings at the phosphorus atom adopt a chair conformation. The Ru complex is co-crystallized with CHCl₃.

Related literature top

For the molecular structure of Ru complexes with the related chlorodiphenylphosphane ligand, see: Jantscher et al. (2009); Torres-Lubián et al. (1999).

Experimental top

A 50 ml round bottom flask with inert gas valve was charged with 0.05 mmol (25 mg) [RuCl₂(η⁶-C₆H₆)]₂ and 4 ml CHCl₃ under argon atmosphere. To this suspension 0.105 mmol (21 µL) chlorodicyclohexylphosphane was added and the reaction mixture was allowed to react 3 h at 323 K. A clear red brown solution has been formed and the volume was reduced carefully in high vacuum to ca 1 ml. Next 20 ml heptane was added to the reaction mixture and cooled for 1 h with ice bath. The precipitate was washed with heptane (3 × 5 ml) to yield the title compound as an orange brown solid (20 mg, 41%). Red single crystals were grown in CHCl₃/heptane mixture at 245 K for 1 day. ¹H NMR (300 MHz), CDCl₃): δ 5.71 (s, 6H, benzene), 2.79 (m, 2H, Cy), 2.06–1.54 (m, 14H, Cy), 1.27 (br s, 6H, Cy). ¹³C {¹H} NMR (75 MHz, CDCl₃): δ 89.8 (RuPh), 40.4 (d, J_PC = 9.5 Hz, PCH), 27.2, 26.9, 26.7, 26.4, 26.3, 26.0, 26.0, 25.6 (CH₂). ³¹P {¹H} NMR (121 MHz, CDCl₃): δ 156.3.

Structure description top

For the molecular structure of Ru complexes with the related chlorodiphenylphosphane ligand, see: Jantscher et al. (2009); Torres-Lubián et al. (1999).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with 30% displacement ellipsoids. Hydrogen atoms are omitted for clarity.

(η⁶-Benzene)dichlorido(chlorodicyclohexylphosphane-κP)ruthenium(II) chloroform monosolvate top

Crystal data top

[RuCl₂(C₆H₆)(C₁₂H₂₂ClP)]·CHCl₃	F(000) = 1216
M_r = 602.16	D_x = 1.705 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.9717 (1) Å	Cell parameters from 9877 reflections
b = 16.3020 (2) Å	θ = 2.3–27.9°
c = 18.0602 (3) Å	µ = 1.42 mm⁻¹
β = 91.244 (1)°	T = 150 K
V = 2346.45 (6) Å³	Prism, orange
Z = 4	0.36 × 0.22 × 0.11 mm

Data collection top

Bruker Kappa APEXII DUO diffractometer	5619 independent reflections
Radiation source: fine-focus sealed tube	4963 reflections with I > 2σ(I)
Curved graphite monochromator	R_int = 0.031
Detector resolution: 8.3333 pixels mm^-1	θ_max = 27.9°, θ_min = 1.7°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −21→21
T_min = 0.630, T_max = 0.859	l = −23→23
37052 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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.048	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0187P)² + 1.4791P] where P = (F_o² + 2F_c²)/3
5619 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[RuCl₂(C₆H₆)(C₁₂H₂₂ClP)]·CHCl₃	V = 2346.45 (6) Å³
M_r = 602.16	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.9717 (1) Å	µ = 1.42 mm⁻¹
b = 16.3020 (2) Å	T = 150 K
c = 18.0602 (3) Å	0.36 × 0.22 × 0.11 mm
β = 91.244 (1)°

Data collection top

Bruker Kappa APEXII DUO diffractometer	5619 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4963 reflections with I > 2σ(I)
T_min = 0.630, T_max = 0.859	R_int = 0.031
37052 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.019	0 restraints
wR(F²) = 0.048	H-atom parameters constrained
S = 1.05	Δρ_max = 0.41 e Å⁻³
5619 reflections	Δρ_min = −0.37 e Å⁻³
244 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	−0.2498 (2)	0.37279 (11)	0.04879 (10)	0.0223 (4)
H1	−0.3279	0.3746	0.0083	0.027*
C2	−0.2406 (2)	0.30292 (11)	0.09373 (10)	0.0227 (4)
H2	−0.3181	0.2592	0.0863	0.027*
C3	−0.1149 (2)	0.29763 (11)	0.15045 (10)	0.0230 (4)
H3	−0.1069	0.2501	0.1808	0.028*
C4	−0.0024 (2)	0.36315 (11)	0.16134 (10)	0.0231 (4)
H4	0.0864	0.3585	0.1970	0.028*
C5	−0.0212 (2)	0.43653 (11)	0.11906 (10)	0.0235 (4)
H5	0.0498	0.4822	0.1291	0.028*
C6	−0.1430 (2)	0.44123 (11)	0.06332 (10)	0.0227 (4)
H6	−0.1552	0.4900	0.0349	0.027*
C7	0.2490 (2)	0.14568 (10)	0.07869 (9)	0.0160 (3)
H7	0.3484	0.1741	0.0577	0.019*
C8	0.2460 (2)	0.16860 (11)	0.16112 (9)	0.0211 (3)
H8A	0.2381	0.2290	0.1661	0.025*
H8B	0.1456	0.1442	0.1837	0.025*
C9	0.4035 (2)	0.13820 (11)	0.20233 (10)	0.0238 (4)
H9A	0.5032	0.1664	0.1828	0.029*
H9B	0.3958	0.1518	0.2556	0.029*
C10	0.4238 (2)	0.04591 (11)	0.19335 (11)	0.0276 (4)
H10A	0.5280	0.0278	0.2193	0.033*
H10B	0.3280	0.0174	0.2160	0.033*
C11	0.4316 (2)	0.02332 (11)	0.11175 (11)	0.0260 (4)
H11A	0.4399	−0.0370	0.1070	0.031*
H11B	0.5337	0.0476	0.0905	0.031*
C12	0.2773 (2)	0.05349 (10)	0.06779 (10)	0.0205 (3)
H12A	0.1771	0.0231	0.0840	0.025*
H12B	0.2924	0.0421	0.0145	0.025*
C13	0.0709 (2)	0.13975 (10)	−0.06377 (9)	0.0161 (3)
H13	0.0799	0.0791	−0.0565	0.019*
C14	−0.0879 (2)	0.15535 (10)	−0.11130 (10)	0.0200 (3)
H14A	−0.1863	0.1318	−0.0865	0.024*
H14B	−0.1060	0.2152	−0.1166	0.024*
C15	−0.0711 (2)	0.11651 (12)	−0.18795 (10)	0.0270 (4)
H15A	−0.0682	0.0561	−0.1828	0.032*
H15B	−0.1705	0.1310	−0.2190	0.032*
C16	0.0864 (3)	0.14489 (13)	−0.22631 (10)	0.0305 (4)
H16A	0.0799	0.2047	−0.2356	0.037*
H16B	0.0953	0.1167	−0.2746	0.037*
C17	0.2405 (2)	0.12592 (12)	−0.17829 (10)	0.0246 (4)
H17A	0.3422	0.1453	−0.2035	0.030*
H17B	0.2503	0.0658	−0.1715	0.030*
C18	0.2299 (2)	0.16729 (10)	−0.10279 (9)	0.0193 (3)
H18A	0.2282	0.2276	−0.1092	0.023*
H18B	0.3298	0.1528	−0.0720	0.023*
C19	0.4349 (2)	0.38768 (11)	0.85956 (10)	0.0222 (4)
H19	0.3475	0.3760	0.8970	0.027*
Cl1	0.01613 (5)	0.35589 (2)	−0.08323 (2)	0.01901 (8)
Cl2	0.30706 (5)	0.34441 (2)	0.04619 (2)	0.02103 (9)
Cl3	−0.12314 (5)	0.11221 (2)	0.07235 (2)	0.02052 (8)
Cl4	0.54297 (6)	0.47752 (3)	0.88609 (3)	0.03089 (10)
Cl5	0.57325 (6)	0.30361 (3)	0.85639 (3)	0.03164 (11)
Cl6	0.33498 (7)	0.40171 (4)	0.77265 (3)	0.03799 (12)
P1	0.06247 (5)	0.18613 (2)	0.02855 (2)	0.01377 (8)
Ru1	0.007356 (16)	0.324634 (7)	0.046687 (7)	0.01356 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0154 (8)	0.0266 (9)	0.0251 (9)	0.0050 (7)	0.0032 (7)	−0.0038 (7)
C2	0.0166 (8)	0.0240 (8)	0.0279 (9)	−0.0015 (7)	0.0095 (7)	−0.0046 (7)
C3	0.0270 (9)	0.0234 (8)	0.0190 (8)	0.0043 (7)	0.0099 (7)	0.0008 (7)
C4	0.0251 (9)	0.0275 (9)	0.0170 (8)	0.0056 (7)	0.0010 (7)	−0.0062 (7)
C5	0.0250 (9)	0.0204 (8)	0.0253 (9)	0.0017 (7)	0.0054 (7)	−0.0085 (7)
C6	0.0232 (9)	0.0191 (8)	0.0260 (9)	0.0067 (7)	0.0067 (7)	−0.0004 (7)
C7	0.0141 (7)	0.0165 (7)	0.0173 (8)	0.0005 (6)	−0.0004 (6)	0.0005 (6)
C8	0.0222 (8)	0.0236 (8)	0.0176 (8)	0.0027 (7)	−0.0016 (7)	−0.0017 (7)
C9	0.0224 (9)	0.0273 (9)	0.0213 (9)	−0.0005 (7)	−0.0066 (7)	0.0002 (7)
C10	0.0218 (9)	0.0260 (9)	0.0344 (10)	−0.0004 (7)	−0.0097 (8)	0.0074 (8)
C11	0.0202 (9)	0.0197 (8)	0.0378 (10)	0.0045 (7)	−0.0052 (8)	−0.0008 (8)
C12	0.0206 (8)	0.0159 (8)	0.0248 (9)	0.0015 (6)	−0.0029 (7)	−0.0004 (7)
C13	0.0174 (8)	0.0145 (7)	0.0165 (8)	−0.0002 (6)	0.0008 (6)	−0.0024 (6)
C14	0.0196 (8)	0.0189 (8)	0.0213 (8)	−0.0024 (6)	−0.0035 (7)	−0.0011 (6)
C15	0.0309 (10)	0.0306 (10)	0.0192 (9)	−0.0067 (8)	−0.0079 (7)	0.0000 (7)
C16	0.0403 (11)	0.0340 (10)	0.0171 (9)	−0.0065 (9)	−0.0011 (8)	0.0025 (8)
C17	0.0279 (9)	0.0283 (9)	0.0178 (8)	0.0010 (8)	0.0057 (7)	−0.0024 (7)
C18	0.0196 (8)	0.0216 (8)	0.0168 (8)	0.0000 (6)	0.0015 (6)	−0.0015 (6)
C19	0.0174 (8)	0.0282 (9)	0.0210 (8)	0.0003 (7)	0.0000 (7)	0.0001 (7)
Cl1	0.02313 (19)	0.01688 (18)	0.01704 (19)	−0.00012 (15)	0.00118 (15)	0.00162 (14)
Cl2	0.01470 (18)	0.02085 (19)	0.0275 (2)	−0.00415 (15)	0.00011 (16)	−0.00070 (16)
Cl3	0.01850 (18)	0.01891 (19)	0.0243 (2)	−0.00493 (15)	0.00428 (15)	0.00082 (15)
Cl4	0.0287 (2)	0.0250 (2)	0.0388 (3)	−0.00293 (18)	−0.0043 (2)	−0.00117 (19)
Cl5	0.0251 (2)	0.0273 (2)	0.0425 (3)	0.00382 (18)	0.0000 (2)	−0.0002 (2)
Cl6	0.0334 (3)	0.0535 (3)	0.0266 (2)	0.0079 (2)	−0.0096 (2)	−0.0028 (2)
P1	0.01298 (18)	0.01378 (18)	0.01459 (19)	−0.00112 (15)	0.00104 (15)	−0.00075 (15)
Ru1	0.01285 (6)	0.01339 (6)	0.01447 (6)	−0.00015 (5)	0.00123 (5)	−0.00095 (5)

Geometric parameters (Å, º) top

C1—C2	1.400 (3)	C11—C12	1.530 (2)
C1—C6	1.425 (2)	C11—H11A	0.9900
C1—Ru1	2.1966 (17)	C11—H11B	0.9900
C1—H1	0.9500	C12—H12A	0.9900
C2—C3	1.420 (3)	C12—H12B	0.9900
C2—Ru1	2.1970 (17)	C13—C18	1.530 (2)
C2—H2	0.9500	C13—C14	1.535 (2)
C3—C4	1.406 (3)	C13—P1	1.8334 (16)
C3—Ru1	2.1759 (17)	C13—H13	1.0000
C3—H3	0.9500	C14—C15	1.531 (2)
C4—C5	1.425 (3)	C14—H14A	0.9900
C4—Ru1	2.1668 (17)	C14—H14B	0.9900
C4—H4	0.9500	C15—C16	1.519 (3)
C5—C6	1.386 (3)	C15—H15A	0.9900
C5—Ru1	2.2585 (17)	C15—H15B	0.9900
C5—H5	0.9500	C16—C17	1.520 (3)
C6—Ru1	2.2705 (17)	C16—H16A	0.9900
C6—H6	0.9500	C16—H16B	0.9900
C7—C12	1.533 (2)	C17—C18	1.525 (2)
C7—C8	1.536 (2)	C17—H17A	0.9900
C7—P1	1.8457 (16)	C17—H17B	0.9900
C7—H7	1.0000	C18—H18A	0.9900
C8—C9	1.528 (2)	C18—H18B	0.9900
C8—H8A	0.9900	C19—Cl6	1.7596 (18)
C8—H8B	0.9900	C19—Cl4	1.7602 (18)
C9—C10	1.522 (3)	C19—Cl5	1.7609 (18)
C9—H9A	0.9900	C19—H19	1.0000
C9—H9B	0.9900	Cl1—Ru1	2.4036 (4)
C10—C11	1.522 (3)	Cl2—Ru1	2.4110 (4)
C10—H10A	0.9900	Cl3—P1	2.0779 (6)
C10—H10B	0.9900	P1—Ru1	2.3247 (4)

C2—C1—C6	120.45 (17)	C15—C14—C13	110.48 (14)
C2—C1—Ru1	71.44 (10)	C15—C14—H14A	109.6
C6—C1—Ru1	74.25 (10)	C13—C14—H14A	109.6
C2—C1—H1	119.8	C15—C14—H14B	109.6
C6—C1—H1	119.8	C13—C14—H14B	109.6
Ru1—C1—H1	126.4	H14A—C14—H14B	108.1
C1—C2—C3	119.69 (16)	C16—C15—C14	112.07 (15)
C1—C2—Ru1	71.41 (10)	C16—C15—H15A	109.2
C3—C2—Ru1	70.25 (10)	C14—C15—H15A	109.2
C1—C2—H2	120.2	C16—C15—H15B	109.2
C3—C2—H2	120.2	C14—C15—H15B	109.2
Ru1—C2—H2	130.8	H15A—C15—H15B	107.9
C4—C3—C2	119.52 (17)	C15—C16—C17	110.09 (15)
C4—C3—Ru1	70.76 (10)	C15—C16—H16A	109.6
C2—C3—Ru1	71.86 (10)	C17—C16—H16A	109.6
C4—C3—H3	120.2	C15—C16—H16B	109.6
C2—C3—H3	120.2	C17—C16—H16B	109.6
Ru1—C3—H3	129.5	H16A—C16—H16B	108.2
C3—C4—C5	120.24 (17)	C16—C17—C18	111.10 (15)
C3—C4—Ru1	71.47 (10)	C16—C17—H17A	109.4
C5—C4—Ru1	74.74 (10)	C18—C17—H17A	109.4
C3—C4—H4	119.9	C16—C17—H17B	109.4
C5—C4—H4	119.9	C18—C17—H17B	109.4
Ru1—C4—H4	125.7	H17A—C17—H17B	108.0
C6—C5—C4	119.95 (17)	C17—C18—C13	110.17 (14)
C6—C5—Ru1	72.66 (10)	C17—C18—H18A	109.6
C4—C5—Ru1	67.75 (9)	C13—C18—H18A	109.6
C6—C5—H5	120.0	C17—C18—H18B	109.6
C4—C5—H5	120.0	C13—C18—H18B	109.6
Ru1—C5—H5	132.5	H18A—C18—H18B	108.1
C5—C6—C1	119.83 (17)	Cl6—C19—Cl4	110.13 (10)
C5—C6—Ru1	71.71 (10)	Cl6—C19—Cl5	110.11 (10)
C1—C6—Ru1	68.61 (9)	Cl4—C19—Cl5	110.69 (9)
C5—C6—H6	120.1	Cl6—C19—H19	108.6
C1—C6—H6	120.1	Cl4—C19—H19	108.6
Ru1—C6—H6	132.6	Cl5—C19—H19	108.6
C12—C7—C8	111.62 (14)	C13—P1—C7	104.70 (7)
C12—C7—P1	114.00 (11)	C13—P1—Cl3	98.49 (5)
C8—C7—P1	111.07 (11)	C7—P1—Cl3	100.29 (6)
C12—C7—H7	106.5	C13—P1—Ru1	122.65 (5)
C8—C7—H7	106.5	C7—P1—Ru1	115.50 (5)
P1—C7—H7	106.5	Cl3—P1—Ru1	111.79 (2)
C9—C8—C7	111.31 (14)	C4—Ru1—C3	37.77 (7)
C9—C8—H8A	109.4	C4—Ru1—C1	80.04 (7)
C7—C8—H8A	109.4	C3—Ru1—C1	67.77 (7)
C9—C8—H8B	109.4	C4—Ru1—C2	68.03 (7)
C7—C8—H8B	109.4	C3—Ru1—C2	37.89 (7)
H8A—C8—H8B	108.0	C1—Ru1—C2	37.15 (7)
C10—C9—C8	110.91 (15)	C4—Ru1—C5	37.51 (7)
C10—C9—H9A	109.5	C3—Ru1—C5	67.19 (7)
C8—C9—H9A	109.5	C1—Ru1—C5	66.15 (7)
C10—C9—H9B	109.5	C2—Ru1—C5	78.67 (7)
C8—C9—H9B	109.5	C4—Ru1—C6	66.48 (7)
H9A—C9—H9B	108.0	C3—Ru1—C6	78.92 (7)
C11—C10—C9	110.42 (15)	C1—Ru1—C6	37.15 (6)
C11—C10—H10A	109.6	C2—Ru1—C6	66.53 (7)
C9—C10—H10A	109.6	C5—Ru1—C6	35.63 (7)
C11—C10—H10B	109.6	C4—Ru1—P1	115.27 (5)
C9—C10—H10B	109.6	C3—Ru1—P1	90.82 (5)
H10A—C10—H10B	108.1	C1—Ru1—P1	121.93 (5)
C10—C11—C12	112.06 (15)	C2—Ru1—P1	94.15 (5)
C10—C11—H11A	109.2	C5—Ru1—P1	152.59 (5)
C12—C11—H11A	109.2	C6—Ru1—P1	159.01 (5)
C10—C11—H11B	109.2	C4—Ru1—Cl1	150.91 (5)
C12—C11—H11B	109.2	C3—Ru1—Cl1	155.05 (5)
H11A—C11—H11B	107.9	C1—Ru1—Cl1	89.32 (5)
C11—C12—C7	111.57 (14)	C2—Ru1—Cl1	117.20 (5)
C11—C12—H12A	109.3	C5—Ru1—Cl1	113.53 (5)
C7—C12—H12A	109.3	C6—Ru1—Cl1	88.76 (5)
C11—C12—H12B	109.3	P1—Ru1—Cl1	93.366 (15)
C7—C12—H12B	109.3	C4—Ru1—Cl2	91.20 (5)
H12A—C12—H12B	108.0	C3—Ru1—Cl2	119.52 (5)
C18—C13—C14	112.01 (14)	C1—Ru1—Cl2	151.36 (5)
C18—C13—P1	110.18 (11)	C2—Ru1—Cl2	157.35 (5)
C14—C13—P1	113.20 (11)	C5—Ru1—Cl2	90.37 (5)
C18—C13—H13	107.0	C6—Ru1—Cl2	114.49 (5)
C14—C13—H13	107.0	P1—Ru1—Cl2	86.505 (14)
P1—C13—H13	107.0	Cl1—Ru1—Cl2	85.306 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···Cl1	0.99	2.56	3.4080 (17)	144
C18—H18A···Cl1	0.99	2.74	3.5366 (17)	138
C19—H19···Cl1ⁱ	1.00	2.69	3.5539 (17)	144
C19—H19···Cl2ⁱ	1.00	2.77	3.6119 (18)	142

Symmetry code: (i) x, y, z+1.