Di-μ2-chlorido-bis­[chlorido(η6-hexa­methyl­benzene)ruthenium(II)]

González-Torres, Y.; Espinosa-Jalapa, N.; Hernández-Ortega, S.; Le Lagadec, R.; Morales-Morales, D.

doi:10.1107/S1600536809041154

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1369

https://doi.org/10.1107/S1600536809041154

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Di-μ₂-chlorido-bis[chlorido(η⁶-hexamethylbenzene)ruthenium(II)]

Yunuem González-Torres,^a Noel Espinosa-Jalapa,^a Simón Hernández-Ortega,^a ^* Ronan Le Lagadec ^a and David Morales-Morales ^a

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México 04510, Mexico
^*Correspondence e-mail: simonho@unam.mx

(Received 29 September 2009; accepted 8 October 2009; online 17 October 2009)

Dimeric molecules of the title compound, [Ru₂Cl₄(C₁₂H₁₈)₂], are located on a crystallographic centre of inversion with one molecule in the asymmetric unit. The hexamethylbenzene rings are in an η⁶-coordination to the ruthenium centres, which are bridged by two chloride ligands. In addition, the ruthenium centres are bonded to another chloride ligand. The aromatic rings and the Ru₂Cl₂ four-membered ring enclose a dihedral angle of 55.85 (6)°.

Related literature

For the properties and potential applications of half-sandwich ruthenium (II) complexes, see: Le Bozec et al. (1989 ); Leyva et al. (2007 ); Ryabov et al. (2001 ). For our work on the synthesis and catalytic applications of different ruthenium–arene complexes, see: Cerón-Camacho et al. (2006 ). For the synthesis, see: Bennett et al. (1982 ).

Experimental

Crystal data

[Ru₂Cl₄(C₁₂H₁₈)₂]
M_r = 668.47
Monoclinic, P 2₁ /n
a = 8.9122 (15) Å
b = 8.5192 (15) Å
c = 16.642 (3) Å
β = 97.084 (3)°
V = 1253.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.64 mm⁻¹
T = 298 K
0.23 × 0.09 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.780, T_max = 0.924
10027 measured reflections
2297 independent reflections
1795 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.063
S = 0.90
2297 reflections
142 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809041154/bt5080sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041154/bt5080Isup2.hkl

checkCIF report

Comment top

For decades, arene ruthenium complexes have played an important role in organometallic chemistry as fundamental precursors for the synthesis of a plethora of species. This is particularly true for the synthesis of half sandwich ruthenium (II) complexes, species that have received considerable attention owing to their potential catalytic properties (Le Bozec et al., 1989), interesting anti-tumor and anti-carcinogenic activity (Leyva et al., 2007) and most recently for their potential applications in chemical and biological sensors (Ryabov, et al., 2001). Thus, given our continuous interest in the synthesis and catalytic applications of different ruthenium arene complexes (Cerón-Camacho et al., 2006) we determined the crystal structure of the title compound.

The asymmetric unit of the title compound consists of a half molecule, which is completed with a symmetry operation of 1 - x, 1 - y, 1 - z. The complex exhibits a typical η⁶ - arene coordination of the hexamethyl fragment to the ruthenium centres which are bridged by two chloro ligands. The coordination sphere of the Ru centres is completed by another chloro ligand. The aromatic rings and the Ru₂Cl₂ four-membered ring enclose a dihedral angle of 55.85 (6)°.

Related literature top

For the properties and potential applications of half-sandwich ruthenium (II) complexes, see: Le Bozec et al. (1989); Leyva et al. (2007); Ryabov et al. (2001). For our work on the synthesis and catalytic applications of different ruthenium–arene complexes, see: Cerón-Camacho et al. (2006). For the synthesis, see: Bennett et al. (1982).

Experimental top

The title compound was prepared according to the procedure reported by Bennett et al. (1982). The spectroscopic analysis agreed with that reported in the same reference.

Structure description top

For the properties and potential applications of half-sandwich ruthenium (II) complexes, see: Le Bozec et al. (1989); Leyva et al. (2007); Ryabov et al. (2001). For our work on the synthesis and catalytic applications of different ruthenium–arene complexes, see: Cerón-Camacho et al. (2006). For the synthesis, see: Bennett et al. (1982).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms omitted.

Di-µ₂-chlorido-bis[chlorido(η⁶-hexamethylbenzene)ruthenium(II)] top

Crystal data top

[Ru₂Cl₄(C₁₂H₁₈)₂]	F(000) = 672
M_r = 668.47	D_x = 1.771 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4016 reflections
a = 8.9122 (15) Å	θ = 2.5–25.3°
b = 8.5192 (15) Å	µ = 1.64 mm⁻¹
c = 16.642 (3) Å	T = 298 K
β = 97.084 (3)°	Prism, red
V = 1253.9 (4) Å³	0.23 × 0.09 × 0.05 mm
Z = 2

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2297 independent reflections
Radiation source: fine-focus sealed tube	1795 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
Detector resolution: 0.83 pixels mm^-1	θ_max = 25.4°, θ_min = 2.5°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 1999)	k = −10→10
T_min = 0.780, T_max = 0.924	l = −20→19
10027 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0193P)²] where P = (F_o² + 2F_c²)/3
2297 reflections	(Δ/σ)_max = 0.001
142 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Ru₂Cl₄(C₁₂H₁₈)₂]	V = 1253.9 (4) Å³
M_r = 668.47	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.9122 (15) Å	µ = 1.64 mm⁻¹
b = 8.5192 (15) Å	T = 298 K
c = 16.642 (3) Å	0.23 × 0.09 × 0.05 mm
β = 97.084 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2297 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	1795 reflections with I > 2σ(I)
T_min = 0.780, T_max = 0.924	R_int = 0.065
10027 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 0.90	Δρ_max = 0.48 e Å⁻³
2297 reflections	Δρ_min = −0.38 e Å⁻³
142 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
Ru1	0.37378 (4)	0.37262 (4)	0.55348 (2)	0.02300 (11)
Cl1	0.24729 (13)	0.30866 (15)	0.42186 (7)	0.0382 (3)
Cl2	0.61218 (11)	0.35592 (12)	0.49415 (6)	0.0297 (3)
C1	0.4006 (5)	0.4464 (5)	0.6809 (2)	0.0316 (11)
C2	0.2421 (5)	0.4425 (5)	0.6495 (2)	0.0293 (10)
C3	0.1792 (5)	0.3056 (5)	0.6121 (2)	0.0281 (10)
C4	0.2721 (5)	0.1702 (5)	0.6053 (3)	0.0312 (11)
C5	0.4287 (5)	0.1741 (5)	0.6343 (3)	0.0341 (11)
C6	0.4913 (5)	0.3142 (6)	0.6727 (2)	0.0325 (11)
C7	0.4686 (6)	0.5943 (6)	0.7198 (3)	0.0524 (15)
H7A	0.3892	0.6661	0.7287	0.063*
H7B	0.5335	0.6420	0.6849	0.063*
H7C	0.5263	0.5688	0.7707	0.063*
C8	0.1465 (5)	0.5866 (5)	0.6552 (3)	0.0458 (13)
H8A	0.1976	0.6762	0.6365	0.055*
H8B	0.1297	0.6027	0.7105	0.055*
H8C	0.0512	0.5729	0.6222	0.055*
C9	0.0143 (5)	0.2997 (6)	0.5765 (3)	0.0451 (13)
H9A	−0.0293	0.4025	0.5784	0.054*
H9B	−0.0391	0.2280	0.6073	0.054*
H9C	0.0068	0.2649	0.5213	0.054*
C10	0.2020 (6)	0.0244 (5)	0.5645 (3)	0.0504 (14)
H10A	0.2759	−0.0580	0.5677	0.060*
H10B	0.1680	0.0470	0.5087	0.060*
H10C	0.1177	−0.0082	0.5911	0.060*
C11	0.5297 (6)	0.0355 (6)	0.6247 (3)	0.0563 (15)
H11A	0.5450	−0.0223	0.6745	0.068*
H11B	0.6254	0.0718	0.6110	0.068*
H11C	0.4832	−0.0313	0.5823	0.068*
C12	0.6585 (5)	0.3210 (6)	0.7036 (3)	0.0537 (15)
H12A	0.6984	0.4212	0.6905	0.064*
H12B	0.7106	0.2392	0.6786	0.064*
H12C	0.6722	0.3069	0.7613	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.02306 (18)	0.02546 (19)	0.02091 (18)	0.00141 (17)	0.00441 (13)	0.00103 (17)
Cl1	0.0363 (7)	0.0503 (8)	0.0268 (6)	−0.0021 (6)	−0.0011 (5)	−0.0047 (5)
Cl2	0.0296 (6)	0.0288 (6)	0.0324 (6)	0.0053 (5)	0.0104 (5)	0.0030 (5)
C1	0.036 (3)	0.042 (3)	0.018 (2)	−0.008 (2)	0.008 (2)	−0.002 (2)
C2	0.033 (3)	0.035 (3)	0.022 (2)	0.007 (2)	0.012 (2)	0.004 (2)
C3	0.027 (2)	0.036 (3)	0.023 (2)	0.000 (2)	0.0078 (19)	0.007 (2)
C4	0.038 (3)	0.029 (3)	0.028 (2)	−0.003 (2)	0.009 (2)	0.006 (2)
C5	0.040 (3)	0.034 (3)	0.030 (3)	0.004 (2)	0.011 (2)	0.010 (2)
C6	0.032 (3)	0.048 (3)	0.018 (2)	0.003 (2)	0.005 (2)	0.011 (2)
C7	0.055 (3)	0.064 (4)	0.040 (3)	−0.014 (3)	0.013 (3)	−0.017 (3)
C8	0.055 (3)	0.040 (3)	0.045 (3)	0.015 (3)	0.018 (3)	−0.006 (2)
C9	0.028 (3)	0.061 (3)	0.047 (3)	−0.005 (3)	0.004 (2)	0.004 (3)
C10	0.055 (3)	0.035 (3)	0.062 (4)	−0.005 (3)	0.010 (3)	−0.003 (3)
C11	0.061 (4)	0.048 (3)	0.061 (4)	0.018 (3)	0.012 (3)	0.010 (3)
C12	0.036 (3)	0.081 (4)	0.042 (3)	0.004 (3)	−0.003 (2)	0.014 (3)

Geometric parameters (Å, º) top

Ru1—C3	2.168 (4)	C5—C11	1.505 (6)
Ru1—C4	2.175 (4)	C6—C12	1.516 (6)
Ru1—C5	2.179 (4)	C7—H7A	0.9600
Ru1—C2	2.179 (4)	C7—H7B	0.9600
Ru1—C6	2.184 (4)	C7—H7C	0.9600
Ru1—C1	2.196 (4)	C8—H8A	0.9600
Ru1—Cl1	2.3993 (12)	C8—H8B	0.9600
Ru1—Cl2ⁱ	2.4528 (11)	C8—H8C	0.9600
Ru1—Cl2	2.4549 (11)	C9—H9A	0.9600
Cl2—Ru1ⁱ	2.4528 (11)	C9—H9B	0.9600
C1—C6	1.403 (6)	C9—H9C	0.9600
C1—C2	1.445 (6)	C10—H10A	0.9600
C1—C7	1.509 (6)	C10—H10B	0.9600
C2—C3	1.406 (6)	C10—H10C	0.9600
C2—C8	1.504 (5)	C11—H11A	0.9600
C3—C4	1.432 (6)	C11—H11B	0.9600
C3—C9	1.516 (6)	C11—H11C	0.9600
C4—C5	1.420 (6)	C12—H12A	0.9600
C4—C10	1.513 (6)	C12—H12B	0.9600
C5—C6	1.435 (6)	C12—H12C	0.9600

C3—Ru1—C4	38.51 (15)	C5—C4—C3	120.5 (4)
C3—Ru1—C5	69.46 (16)	C5—C4—C10	120.4 (4)
C4—Ru1—C5	38.06 (15)	C3—C4—C10	119.1 (4)
C3—Ru1—C2	37.75 (15)	C5—C4—Ru1	71.1 (2)
C4—Ru1—C2	68.75 (16)	C3—C4—Ru1	70.5 (2)
C5—Ru1—C2	81.93 (16)	C10—C4—Ru1	129.9 (3)
C3—Ru1—C6	81.49 (16)	C4—C5—C6	118.9 (4)
C4—Ru1—C6	68.64 (16)	C4—C5—C11	121.4 (4)
C5—Ru1—C6	38.39 (16)	C6—C5—C11	119.7 (4)
C2—Ru1—C6	68.72 (16)	C4—C5—Ru1	70.8 (2)
C3—Ru1—C1	68.85 (16)	C6—C5—Ru1	71.0 (2)
C4—Ru1—C1	81.11 (16)	C11—C5—Ru1	129.4 (3)
C5—Ru1—C1	68.71 (17)	C1—C6—C5	120.9 (4)
C2—Ru1—C1	38.56 (16)	C1—C6—C12	119.4 (4)
C6—Ru1—C1	37.35 (16)	C5—C6—C12	119.7 (4)
C3—Ru1—Cl1	92.23 (12)	C1—C6—Ru1	71.8 (2)
C4—Ru1—Cl1	90.57 (12)	C5—C6—Ru1	70.6 (2)
C5—Ru1—Cl1	115.57 (13)	C12—C6—Ru1	129.8 (3)
C2—Ru1—Cl1	119.79 (12)	C1—C7—H7A	109.5
C6—Ru1—Cl1	153.69 (13)	C1—C7—H7B	109.5
C1—Ru1—Cl1	158.35 (12)	H7A—C7—H7B	109.5
C3—Ru1—Cl2ⁱ	117.98 (12)	C1—C7—H7C	109.5
C4—Ru1—Cl2ⁱ	156.34 (12)	H7A—C7—H7C	109.5
C5—Ru1—Cl2ⁱ	156.20 (13)	H7B—C7—H7C	109.5
C2—Ru1—Cl2ⁱ	91.89 (12)	C2—C8—H8A	109.5
C6—Ru1—Cl2ⁱ	118.07 (13)	C2—C8—H8B	109.5
C1—Ru1—Cl2ⁱ	92.19 (12)	H8A—C8—H8B	109.5
Cl1—Ru1—Cl2ⁱ	87.48 (4)	C2—C8—H8C	109.5
C3—Ru1—Cl2	160.99 (12)	H8A—C8—H8C	109.5
C4—Ru1—Cl2	122.48 (12)	H8B—C8—H8C	109.5
C5—Ru1—Cl2	93.65 (12)	C3—C9—H9A	109.5
C2—Ru1—Cl2	151.86 (12)	C3—C9—H9B	109.5
C6—Ru1—Cl2	90.59 (12)	H9A—C9—H9B	109.5
C1—Ru1—Cl2	114.09 (12)	C3—C9—H9C	109.5
Cl1—Ru1—Cl2	87.26 (4)	H9A—C9—H9C	109.5
Cl2ⁱ—Ru1—Cl2	81.00 (4)	H9B—C9—H9C	109.5
Ru1ⁱ—Cl2—Ru1	99.00 (4)	C4—C10—H10A	109.5
C6—C1—C2	119.7 (4)	C4—C10—H10B	109.5
C6—C1—C7	120.4 (4)	H10A—C10—H10B	109.5
C2—C1—C7	119.8 (4)	C4—C10—H10C	109.5
C6—C1—Ru1	70.9 (2)	H10A—C10—H10C	109.5
C2—C1—Ru1	70.1 (2)	H10B—C10—H10C	109.5
C7—C1—Ru1	130.1 (3)	C5—C11—H11A	109.5
C3—C2—C1	119.8 (4)	C5—C11—H11B	109.5
C3—C2—C8	120.5 (4)	H11A—C11—H11B	109.5
C1—C2—C8	119.7 (4)	C5—C11—H11C	109.5
C3—C2—Ru1	70.7 (2)	H11A—C11—H11C	109.5
C1—C2—Ru1	71.3 (2)	H11B—C11—H11C	109.5
C8—C2—Ru1	129.0 (3)	C6—C12—H12A	109.5
C2—C3—C4	120.0 (4)	C6—C12—H12B	109.5
C2—C3—C9	121.0 (4)	H12A—C12—H12B	109.5
C4—C3—C9	119.0 (4)	C6—C12—H12C	109.5
C2—C3—Ru1	71.6 (2)	H12A—C12—H12C	109.5
C4—C3—Ru1	71.0 (2)	H12B—C12—H12C	109.5
C9—C3—Ru1	128.6 (3)

C3—Ru1—Cl2—Ru1ⁱ	176.8 (4)	C9—C3—C4—C10	−1.3 (6)
C4—Ru1—Cl2—Ru1ⁱ	176.81 (14)	Ru1—C3—C4—C10	−125.6 (4)
C5—Ru1—Cl2—Ru1ⁱ	−156.66 (13)	C2—C3—C4—Ru1	−54.2 (3)
C2—Ru1—Cl2—Ru1ⁱ	−77.0 (2)	C9—C3—C4—Ru1	124.3 (4)
C6—Ru1—Cl2—Ru1ⁱ	−118.35 (13)	C3—Ru1—C4—C5	−133.7 (4)
C1—Ru1—Cl2—Ru1ⁱ	−88.37 (14)	C2—Ru1—C4—C5	−104.6 (3)
Cl1—Ru1—Cl2—Ru1ⁱ	87.88 (4)	C6—Ru1—C4—C5	−30.0 (3)
Cl2ⁱ—Ru1—Cl2—Ru1ⁱ	0.0	C1—Ru1—C4—C5	−66.6 (3)
C3—Ru1—C1—C6	104.2 (3)	Cl1—Ru1—C4—C5	133.4 (2)
C4—Ru1—C1—C6	66.3 (3)	Cl2ⁱ—Ru1—C4—C5	−141.6 (3)
C5—Ru1—C1—C6	28.9 (3)	Cl2—Ru1—C4—C5	46.3 (3)
C2—Ru1—C1—C6	133.2 (4)	C5—Ru1—C4—C3	133.7 (4)
Cl1—Ru1—C1—C6	134.7 (3)	C2—Ru1—C4—C3	29.1 (2)
Cl2ⁱ—Ru1—C1—C6	−136.6 (2)	C6—Ru1—C4—C3	103.7 (3)
Cl2—Ru1—C1—C6	−55.4 (3)	C1—Ru1—C4—C3	67.1 (3)
C3—Ru1—C1—C2	−29.0 (2)	Cl1—Ru1—C4—C3	−92.9 (2)
C4—Ru1—C1—C2	−66.9 (3)	Cl2ⁱ—Ru1—C4—C3	−7.8 (5)
C5—Ru1—C1—C2	−104.3 (3)	Cl2—Ru1—C4—C3	−180.0 (2)
C6—Ru1—C1—C2	−133.2 (4)	C3—Ru1—C4—C10	112.1 (5)
Cl1—Ru1—C1—C2	1.6 (5)	C5—Ru1—C4—C10	−114.2 (5)
Cl2ⁱ—Ru1—C1—C2	90.3 (2)	C2—Ru1—C4—C10	141.1 (5)
Cl2—Ru1—C1—C2	171.4 (2)	C6—Ru1—C4—C10	−144.3 (5)
C3—Ru1—C1—C7	−141.7 (5)	C1—Ru1—C4—C10	179.1 (4)
C4—Ru1—C1—C7	−179.6 (5)	Cl1—Ru1—C4—C10	19.2 (4)
C5—Ru1—C1—C7	143.0 (5)	Cl2ⁱ—Ru1—C4—C10	104.2 (4)
C2—Ru1—C1—C7	−112.7 (5)	Cl2—Ru1—C4—C10	−67.9 (4)
C6—Ru1—C1—C7	114.1 (5)	C3—C4—C5—C6	1.9 (6)
Cl1—Ru1—C1—C7	−111.1 (4)	C10—C4—C5—C6	−180.0 (4)
Cl2ⁱ—Ru1—C1—C7	−22.4 (4)	Ru1—C4—C5—C6	54.2 (4)
Cl2—Ru1—C1—C7	58.7 (5)	C3—C4—C5—C11	−177.4 (4)
C6—C1—C2—C3	0.9 (6)	C10—C4—C5—C11	0.7 (6)
C7—C1—C2—C3	179.0 (4)	Ru1—C4—C5—C11	−125.1 (4)
Ru1—C1—C2—C3	53.4 (3)	C3—C4—C5—Ru1	−52.3 (3)
C6—C1—C2—C8	−177.4 (4)	C10—C4—C5—Ru1	125.9 (4)
C7—C1—C2—C8	0.7 (6)	C3—Ru1—C5—C4	28.7 (3)
Ru1—C1—C2—C8	−124.9 (4)	C2—Ru1—C5—C4	65.6 (3)
C6—C1—C2—Ru1	−52.5 (3)	C6—Ru1—C5—C4	131.3 (4)
C7—C1—C2—Ru1	125.6 (4)	C1—Ru1—C5—C4	103.2 (3)
C4—Ru1—C2—C3	−29.6 (2)	Cl1—Ru1—C5—C4	−53.6 (3)
C5—Ru1—C2—C3	−66.7 (3)	Cl2ⁱ—Ru1—C5—C4	141.8 (3)
C6—Ru1—C2—C3	−104.1 (3)	Cl2—Ru1—C5—C4	−142.3 (2)
C1—Ru1—C2—C3	−132.4 (4)	C3—Ru1—C5—C6	−102.6 (3)
Cl1—Ru1—C2—C3	48.2 (3)	C4—Ru1—C5—C6	−131.3 (4)
Cl2ⁱ—Ru1—C2—C3	136.4 (2)	C2—Ru1—C5—C6	−65.7 (3)
Cl2—Ru1—C2—C3	−149.3 (2)	C1—Ru1—C5—C6	−28.1 (2)
C3—Ru1—C2—C1	132.4 (4)	Cl1—Ru1—C5—C6	175.0 (2)
C4—Ru1—C2—C1	102.8 (3)	Cl2ⁱ—Ru1—C5—C6	10.5 (5)
C5—Ru1—C2—C1	65.8 (3)	Cl2—Ru1—C5—C6	86.3 (2)
C6—Ru1—C2—C1	28.4 (3)	C3—Ru1—C5—C11	144.1 (5)
Cl1—Ru1—C2—C1	−179.3 (2)	C4—Ru1—C5—C11	115.4 (5)
Cl2ⁱ—Ru1—C2—C1	−91.2 (2)	C2—Ru1—C5—C11	−179.0 (5)
Cl2—Ru1—C2—C1	−16.8 (4)	C6—Ru1—C5—C11	−113.2 (5)
C3—Ru1—C2—C8	−114.0 (5)	C1—Ru1—C5—C11	−141.4 (5)
C4—Ru1—C2—C8	−143.7 (5)	Cl1—Ru1—C5—C11	61.8 (5)
C5—Ru1—C2—C8	179.3 (4)	Cl2ⁱ—Ru1—C5—C11	−102.8 (5)
C6—Ru1—C2—C8	141.9 (5)	Cl2—Ru1—C5—C11	−26.9 (4)
C1—Ru1—C2—C8	113.5 (5)	C2—C1—C6—C5	−0.6 (6)
Cl1—Ru1—C2—C8	−65.8 (4)	C7—C1—C6—C5	−178.7 (4)
Cl2ⁱ—Ru1—C2—C8	22.4 (4)	Ru1—C1—C6—C5	−52.8 (4)
Cl2—Ru1—C2—C8	96.7 (4)	C2—C1—C6—C12	178.2 (4)
C1—C2—C3—C4	0.2 (6)	C7—C1—C6—C12	0.1 (6)
C8—C2—C3—C4	178.5 (4)	Ru1—C1—C6—C12	126.1 (4)
Ru1—C2—C3—C4	53.9 (3)	C2—C1—C6—Ru1	52.2 (3)
C1—C2—C3—C9	−178.3 (4)	C7—C1—C6—Ru1	−125.9 (4)
C8—C2—C3—C9	0.0 (6)	C4—C5—C6—C1	−0.8 (6)
Ru1—C2—C3—C9	−124.5 (4)	C11—C5—C6—C1	178.5 (4)
C1—C2—C3—Ru1	−53.7 (3)	Ru1—C5—C6—C1	53.3 (4)
C8—C2—C3—Ru1	124.6 (4)	C4—C5—C6—C12	−179.6 (4)
C4—Ru1—C3—C2	132.3 (4)	C11—C5—C6—C12	−0.3 (6)
C5—Ru1—C3—C2	103.8 (3)	Ru1—C5—C6—C12	−125.5 (4)
C6—Ru1—C3—C2	66.0 (3)	C4—C5—C6—Ru1	−54.1 (4)
C1—Ru1—C3—C2	29.6 (2)	C11—C5—C6—Ru1	125.2 (4)
Cl1—Ru1—C3—C2	−139.6 (2)	C3—Ru1—C6—C1	−66.1 (3)
Cl2ⁱ—Ru1—C3—C2	−51.3 (3)	C4—Ru1—C6—C1	−103.8 (3)
Cl2—Ru1—C3—C2	132.3 (3)	C5—Ru1—C6—C1	−133.6 (4)
C5—Ru1—C3—C4	−28.4 (2)	C2—Ru1—C6—C1	−29.2 (2)
C2—Ru1—C3—C4	−132.3 (4)	Cl1—Ru1—C6—C1	−143.8 (3)
C6—Ru1—C3—C4	−66.2 (3)	Cl2ⁱ—Ru1—C6—C1	51.1 (3)
C1—Ru1—C3—C4	−102.7 (3)	Cl2—Ru1—C6—C1	131.2 (2)
Cl1—Ru1—C3—C4	88.1 (2)	C3—Ru1—C6—C5	67.5 (3)
Cl2ⁱ—Ru1—C3—C4	176.4 (2)	C4—Ru1—C6—C5	29.8 (2)
Cl2—Ru1—C3—C4	0.0 (5)	C2—Ru1—C6—C5	104.4 (3)
C4—Ru1—C3—C9	−112.4 (5)	C1—Ru1—C6—C5	133.6 (4)
C5—Ru1—C3—C9	−140.8 (4)	Cl1—Ru1—C6—C5	−10.1 (4)
C2—Ru1—C3—C9	115.4 (5)	Cl2ⁱ—Ru1—C6—C5	−175.2 (2)
C6—Ru1—C3—C9	−178.6 (4)	Cl2—Ru1—C6—C5	−95.1 (2)
C1—Ru1—C3—C9	144.9 (5)	C3—Ru1—C6—C12	−179.5 (5)
Cl1—Ru1—C3—C9	−24.3 (4)	C4—Ru1—C6—C12	142.7 (5)
Cl2ⁱ—Ru1—C3—C9	64.1 (4)	C5—Ru1—C6—C12	113.0 (6)
Cl2—Ru1—C3—C9	−112.3 (4)	C2—Ru1—C6—C12	−142.6 (5)
C2—C3—C4—C5	−1.7 (6)	C1—Ru1—C6—C12	−113.4 (6)
C9—C3—C4—C5	176.9 (4)	Cl1—Ru1—C6—C12	102.8 (5)
Ru1—C3—C4—C5	52.5 (4)	Cl2ⁱ—Ru1—C6—C12	−62.3 (5)
C2—C3—C4—C10	−179.8 (4)	Cl2—Ru1—C6—C12	17.8 (4)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ru₂Cl₄(C₁₂H₁₈)₂]
M_r	668.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.9122 (15), 8.5192 (15), 16.642 (3)
β (°)	97.084 (3)
V (Å³)	1253.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.64
Crystal size (mm)	0.23 × 0.09 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.780, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	10027, 2297, 1795
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.063, 0.90
No. of reflections	2297
No. of parameters	142
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.38

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXTL (Sheldrick, 2008).

Acknowledgements

The financial support of this research by CONACYT (F58692, 57556) and DGAPA-UNAM (IN227008, IN205209) is gratefully acknowledged.

References

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