trans-Bis[1,2-bis­(diphenyl­phosphan­yl)ethane]­chlorido(ethyn­yl)ruthenium(II)

Trujillo, A.; Fuentealba, M.; Arratia-Perez, R.; Howard, J.A.K.

doi:10.1107/S1600536812044558

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1445

doi:10.1107/S1600536812044558

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trans-Bis[1,2-bis(diphenylphosphanyl)ethane]chlorido(ethynyl)ruthenium(II)

Alexander Trujillo,^a ^* Mauricio Fuentealba,^b Ramiro Arratia-Perez ^a and Judith A. K. Howard ^c

^aDepartamento de Ciencias Quimicas, Facultad de Ciencias Exactas, Universidad Andres Bello, Avenida Republica 275, Santiago, Chile, ^bInstituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Avenida Universidad 330, Curauma, Valparaíso, Chile, and ^cDepartment of Chemistry, University of Durham, South Road, Durham DH1 3LE, England
^*Correspondence e-mail: al.trujillo@uandresbello.edu

(Received 29 September 2012; accepted 28 October 2012; online 3 November 2012)

The molecular structure of the title compound, trans-[Cu(C₂H)Cl(C₂₆H₂₄P₂)₂], consists of an Ru^II cation, located on an inversion centre, in an octahedral environment defined by two chelating phosphines, one acetylide and one chloride ligand. The –C≡CH and the chlorine ligands are disordered over two equivalent positions (0.5 occupancy each). The coordination geometry is distorted octahedral, with the –C≡CH fragment and the Cl ligand in trans positions. The four P atoms occupy the equatorial plane of the octahedron and the chloride and acetylide ligands the axial positions.

Related literature

For details of electronic communication, see: Hu et al. (2005 ) and for molecular electronics, see: Gauthier et al. (2008 ). For the chemistry of the trans-RuCl(C≡CH)(dppe)₂, [dppe = 1,2-bis(diphenylphosphanyl)ethane] complex, see: Fox et al. (2009 ). For related structures, see: Faulkner et al. (1994 ); Zhu et al. (1999 ); Younus et al. (1999 ).

Experimental

Crystal data

[Cu(C₂H)Cl(C₂₆H₂₄P₂)₂]
M_r = 958.33
Monoclinic, P 2₁ /n
a = 10.92406 (18) Å
b = 16.0826 (2) Å
c = 13.2228 (2) Å
β = 105.2553 (17)°
V = 2241.22 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 120 K
0.41 × 0.35 × 0.20 mm

Data collection

Agilent Xcalibur (Sapphire3, Gemini ultra) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.912, T_max = 1.000
32289 measured reflections
6470 independent reflections
5653 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.072
S = 1.09
6470 reflections
293 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ).; software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812044558/bg2483sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044558/bg2483Isup2.hkl

checkCIF report

Comment top

In recent years, the design of carbon-rich organometallics compounds has been an interesting research topic, because in this type of structures the connection between the metal center with functional groups is achieved, and consequently the electronic communication is allowed through the C≡C unit (Hu et al., 2005). Therefore, much attention has had the chemistry of the trans-RuCl(C≡CH)(dppe)2, [dppe= 1,2-Bis(diphenylphosphanyl)ethane] complex (Fox et al., 2009). The Cl(dppe)2Ru—C≡C– endgroups behave as strongly electron-releasing groups which compares favorably to organic electron-releasing substituents such as methoxy or amino substituents. Moreover, in contrast to the organic substituents, these mononuclear organometallic acetylide complexes exhibit usually a very electron-rich chemistry and constitute a remarkable potential use in the molecular electronics field, since the oxidation state of the metal can be easily modulated (Gauthier et al., 2008). In addition, these types of fragments have been shown to be interesting when they are attached to various unsaturated bridges. Depending on the nature of the bridge and the type of design obtained, they can exhibit different magnetic, optical or electronic properties (Faulkner et al., 1994; Zhu et al., 1999). Despite its important and widely use in the organometallic chemistry for the syntheses of vinylidene ruthenium complexes, for his rich electronic properties, the molecular structure of complex (1) has not been previously reported.

The main compound (1) crystallizes in the monoclinic space group P2₁/n. The structure lies over a special position located in an inversion centre. the –C≡CH and the chlorine ligands are disordered over two equivalent positions (0.5 occupancy each one). The coordination geometry is a distorted octahedron with the –C≡CH fragment and the Cl ligand in trans position.

The structure of (1) shows four phosphorus atoms occupying the equatorial plane of the octahedron and the chloride and acetylide ligands occupying the axial position in trans configuration. The Cl—Ru, Ru—C(1), and C(1)—C(2) data for this complex fall within the range of those previously reported for related octahedral trans-bis(bidentate phosphine) ruthenium alkynyl complexes (Younus et al., 1999).

Finally, both inter- and intramolecular hydrogen bonds or any other kind interaction are not observed in the crystalline packing of title compound.

Related literature top

For details of electronic communication, see: Hu et al. (2005) and for molecular electronics, see: Gauthier et al. (2008). For the chemistry of the trans-RuCl(C≡CH)(dppe)₂, [dppe= 1,2-bis(diphenylphosphanyl)ethane] complex, see Fox et al. (2009). For related structures, see: Faulkner et al. (1994); Zhu et al. (1999); Younus et al. (1999).

Experimental top

A Schlenk tube under argon was loaded with [Ru(dppe)₂Cl]⁺ (0.400 g, 0.369 mmol), ethynyltrimethylsilane (100 ml, 0.71 mmol), and 20 ml CH₂Cl₂ was added. The resulting mixture was stirred over night. After evaporation of the solvent, the residue was extracted with CH₂Cl₂ and chromatographied through a 2x4 cm Al₂O₃ column using CH₂Cl₂ as eluant. The solution was evaporated and the remaining solid was washed with n-pentane and dried in vacuo, to afford (1) as an yellow powder (0.262 g, 68,5%). Crystals were obtained by vapor diffusion of dichloromethane and hexane solution of (1).

Structure description top

Finally, both inter- and intramolecular hydrogen bonds or any other kind interaction are not observed in the crystalline packing of title compound.

For details of electronic communication, see: Hu et al. (2005) and for molecular electronics, see: Gauthier et al. (2008). For the chemistry of the trans-RuCl(C≡CH)(dppe)₂, [dppe= 1,2-bis(diphenylphosphanyl)ethane] complex, see Fox et al. (2009). For related structures, see: Faulkner et al. (1994); Zhu et al. (1999); Younus et al. (1999).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009).; software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of title compound with full atom numbering scheme for indepent atoms. Displacement ellipsoids are presented at 50% probability level. Hydrogen atoms and disordered phenyl ring have been omitted in sake of clarity.

trans-Bis[1,2- bis(diphenylphosphanyl)ethane]chlorido(ethynyl)ruthenium(II) top

Crystal data top

[Cu(C₂H)Cl(C₂₆H₂₄P₂)₂]	F(000) = 988
M_r = 958.33	D_x = 1.420 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.7107 Å
a = 10.92406 (18) Å	Cell parameters from 13838 reflections
b = 16.0826 (2) Å	θ = 2.5–30.8°
c = 13.2228 (2) Å	µ = 0.59 mm⁻¹
β = 105.2553 (17)°	T = 120 K
V = 2241.22 (6) Å³	Polyhedron, yellow
Z = 2	0.41 × 0.35 × 0.20 mm

Data collection top

Agilent Xcalibur (Sapphire3, Gemini ultra) diffractometer	6470 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5653 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 16.1511 pixels mm^-1	θ_max = 30.8°, θ_min = 2.5°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −22→23
T_min = 0.912, T_max = 1.000	l = −18→18
32289 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0263P)² + 1.1519P] where P = (F_o² + 2F_c²)/3
6470 reflections	(Δ/σ)_max < 0.001
293 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Cu(C₂H)Cl(C₂₆H₂₄P₂)₂]	V = 2241.22 (6) Å³
M_r = 958.33	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.92406 (18) Å	µ = 0.59 mm⁻¹
b = 16.0826 (2) Å	T = 120 K
c = 13.2228 (2) Å	0.41 × 0.35 × 0.20 mm
β = 105.2553 (17)°

Data collection top

Agilent Xcalibur (Sapphire3, Gemini ultra) diffractometer	6470 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	5653 reflections with I > 2σ(I)
T_min = 0.912, T_max = 1.000	R_int = 0.040
32289 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.09	Δρ_max = 0.49 e Å⁻³
6470 reflections	Δρ_min = −0.48 e Å⁻³
293 parameters

Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. (Agilent Technologies, 2011)

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	Occ. (<1)
Ru1	0.0000	0.0000	0.0000	0.01370 (5)
Cl1	0.23554 (13)	0.03894 (6)	0.07756 (9)	0.0164 (2)	0.50
P1	−0.00132 (4)	0.01938 (2)	0.17791 (3)	0.01557 (8)
P2	−0.03740 (4)	0.14451 (2)	−0.00604 (3)	0.01542 (8)
C1	−0.1785 (5)	−0.0277 (2)	−0.0475 (3)	0.0159 (7)	0.50
C2	−0.2870 (5)	−0.0472 (3)	−0.0780 (4)	0.0182 (10)	0.50
H2	−0.3736	−0.0629	−0.1024	0.022*	0.50
C3	−0.1320 (5)	−0.0010 (3)	0.2384 (4)	0.0177 (7)	0.725 (17)
C4	−0.2548 (5)	−0.0110 (3)	0.1755 (4)	0.0240 (9)	0.725 (17)
H4	−0.2709	−0.0086	0.1013	0.029*	0.725 (17)
C5	−0.3543 (5)	−0.0244 (3)	0.2209 (6)	0.0328 (12)	0.725 (17)
H5	−0.4382	−0.0312	0.1779	0.039*	0.725 (17)
C6	−0.3308 (6)	−0.0280 (3)	0.3294 (6)	0.0332 (12)	0.725 (17)
H6	−0.3988	−0.0372	0.3605	0.040*	0.725 (17)
C7	−0.2080 (6)	−0.0180 (3)	0.3924 (5)	0.0354 (11)	0.725 (17)
H7	−0.1919	−0.0204	0.4665	0.042*	0.725 (17)
C8	−0.1085 (5)	−0.0046 (4)	0.3469 (4)	0.0276 (9)	0.725 (17)
H8	−0.0246	0.0022	0.3899	0.033*	0.725 (17)
C3A	−0.1411 (13)	−0.0092 (11)	0.2247 (11)	0.0177 (7)	0.275 (17)
C4A	−0.2629 (15)	0.0009 (12)	0.1584 (10)	0.0240 (9)	0.275 (17)
H4A	−0.2741	0.0161	0.0871	0.029*	0.275 (17)
C5A	−0.3695 (12)	−0.0117 (11)	0.1984 (12)	0.0328 (12)	0.275 (17)
H5A	−0.4522	−0.0067	0.1525	0.039*	0.275 (17)
C6A	−0.3573 (14)	−0.0301 (10)	0.2973 (13)	0.0332 (12)	0.275 (17)
H6A	−0.4299	−0.0460	0.3194	0.040*	0.275 (17)
C7A	−0.2455 (16)	−0.0268 (9)	0.3665 (11)	0.0354 (11)	0.275 (17)
H7A	−0.2396	−0.0303	0.4394	0.042*	0.275 (17)
C8A	−0.1349 (13)	−0.0181 (11)	0.3314 (11)	0.0276 (9)	0.275 (17)
H8A	−0.0544	−0.0181	0.3812	0.033*	0.275 (17)
C9	0.13110 (15)	−0.02627 (10)	0.27746 (12)	0.0187 (3)
C10	0.12128 (17)	−0.10699 (11)	0.31425 (13)	0.0225 (3)
H10	0.0450	−0.1376	0.2886	0.027*
C11	0.22226 (19)	−0.14261 (12)	0.38806 (14)	0.0302 (4)
H11	0.2148	−0.1974	0.4125	0.036*
C12	0.33340 (19)	−0.09861 (14)	0.42603 (14)	0.0339 (5)
H12	0.4022	−0.1230	0.4766	0.041*
C13	0.34422 (18)	−0.01890 (13)	0.39024 (15)	0.0300 (4)
H13	0.4207	0.0114	0.4163	0.036*
C14	0.24357 (16)	0.01729 (12)	0.31609 (14)	0.0241 (4)
H14	0.2519	0.0721	0.2918	0.029*
C15	0.01206 (16)	0.13281 (10)	0.20793 (12)	0.0195 (3)
H15A	−0.0705	0.1533	0.2157	0.023*
H15B	0.0760	0.1413	0.2757	0.023*
C16	0.04975 (16)	0.18398 (10)	0.12365 (12)	0.0190 (3)
H16A	0.1423	0.1793	0.1321	0.023*
H16B	0.0289	0.2433	0.1304	0.023*
C17	−0.19892 (15)	0.18361 (10)	−0.02263 (12)	0.0180 (3)
C18	−0.22999 (17)	0.24080 (11)	0.04617 (14)	0.0257 (4)
H18	−0.1660	0.2599	0.1051	0.031*
C19	−0.35332 (19)	0.27016 (13)	0.02957 (15)	0.0326 (4)
H19	−0.3733	0.3085	0.0776	0.039*
C20	−0.44647 (18)	0.24394 (13)	−0.05609 (16)	0.0329 (4)
H20	−0.5309	0.2637	−0.0671	0.039*
C21	−0.41672 (17)	0.18843 (12)	−0.12658 (15)	0.0289 (4)
H21	−0.4806	0.1713	−0.1867	0.035*
C22	−0.29422 (16)	0.15783 (10)	−0.10961 (13)	0.0225 (3)
H22	−0.2751	0.1191	−0.1575	0.027*
C23	0.02017 (15)	0.21231 (10)	−0.09510 (12)	0.0180 (3)
C24	−0.05139 (18)	0.27775 (11)	−0.14948 (14)	0.0251 (4)
H24	−0.1326	0.2895	−0.1395	0.030*
C25	−0.0045 (2)	0.32590 (12)	−0.21821 (16)	0.0337 (4)
H25	−0.0538	0.3706	−0.2547	0.040*
C26	0.1133 (2)	0.30913 (12)	−0.23390 (16)	0.0318 (4)
H26	0.1447	0.3419	−0.2814	0.038*
C27	0.18501 (18)	0.24436 (11)	−0.18002 (14)	0.0265 (4)
H27	0.2659	0.2326	−0.1908	0.032*
C28	0.13984 (16)	0.19629 (10)	−0.11019 (13)	0.0214 (3)
H28	0.1904	0.1525	−0.0727	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.01802 (9)	0.00967 (8)	0.01496 (9)	0.00060 (6)	0.00706 (6)	0.00112 (6)
Cl1	0.0137 (7)	0.0166 (5)	0.0174 (5)	−0.0028 (5)	0.0015 (5)	0.0003 (3)
P1	0.01879 (19)	0.01286 (18)	0.01658 (19)	0.00130 (14)	0.00734 (15)	0.00160 (14)
P2	0.01964 (19)	0.01067 (17)	0.01706 (19)	0.00060 (14)	0.00677 (15)	0.00072 (14)
C1	0.022 (2)	0.0135 (16)	0.0144 (18)	−0.0002 (16)	0.0080 (15)	0.0004 (13)
C2	0.010 (2)	0.025 (2)	0.0165 (17)	−0.0044 (19)	−0.0013 (18)	0.0015 (13)
C3	0.0248 (11)	0.0106 (14)	0.0214 (16)	0.0001 (9)	0.0124 (12)	−0.0042 (12)
C4	0.0246 (12)	0.022 (2)	0.0288 (18)	0.0007 (12)	0.0125 (13)	−0.0040 (14)
C5	0.0248 (16)	0.027 (2)	0.051 (3)	−0.0008 (13)	0.0187 (18)	−0.0077 (18)
C6	0.035 (2)	0.0332 (12)	0.041 (3)	0.0019 (15)	0.027 (3)	0.0003 (19)
C7	0.026 (3)	0.0582 (19)	0.026 (2)	0.013 (2)	0.014 (2)	0.0114 (17)
C8	0.022 (2)	0.040 (2)	0.0226 (17)	0.0032 (15)	0.0101 (16)	0.0014 (13)
C3A	0.0248 (11)	0.0106 (14)	0.0214 (16)	0.0001 (9)	0.0124 (12)	−0.0042 (12)
C4A	0.0246 (12)	0.022 (2)	0.0288 (18)	0.0007 (12)	0.0125 (13)	−0.0040 (14)
C5A	0.0248 (16)	0.027 (2)	0.051 (3)	−0.0008 (13)	0.0187 (18)	−0.0077 (18)
C6A	0.035 (2)	0.0332 (12)	0.041 (3)	0.0019 (15)	0.027 (3)	0.0003 (19)
C7A	0.026 (3)	0.0582 (19)	0.026 (2)	0.013 (2)	0.014 (2)	0.0114 (17)
C8A	0.022 (2)	0.040 (2)	0.0226 (17)	0.0032 (15)	0.0101 (16)	0.0014 (13)
C9	0.0226 (8)	0.0195 (8)	0.0156 (7)	0.0052 (6)	0.0074 (6)	0.0015 (6)
C10	0.0300 (9)	0.0200 (8)	0.0189 (8)	0.0050 (7)	0.0087 (7)	0.0003 (6)
C11	0.0444 (11)	0.0243 (9)	0.0211 (9)	0.0152 (8)	0.0073 (8)	0.0041 (7)
C12	0.0346 (10)	0.0415 (12)	0.0221 (9)	0.0197 (9)	0.0014 (8)	−0.0002 (8)
C13	0.0219 (8)	0.0421 (11)	0.0254 (9)	0.0057 (8)	0.0050 (7)	−0.0037 (8)
C14	0.0233 (8)	0.0280 (9)	0.0228 (8)	0.0016 (7)	0.0091 (7)	0.0010 (7)
C15	0.0284 (8)	0.0133 (7)	0.0173 (7)	0.0024 (6)	0.0068 (6)	−0.0014 (6)
C16	0.0238 (8)	0.0130 (7)	0.0199 (7)	−0.0013 (6)	0.0054 (6)	−0.0006 (6)
C17	0.0217 (8)	0.0126 (7)	0.0214 (8)	0.0024 (6)	0.0086 (6)	0.0035 (6)
C18	0.0319 (9)	0.0235 (9)	0.0222 (8)	0.0087 (7)	0.0080 (7)	0.0011 (7)
C19	0.0386 (11)	0.0331 (10)	0.0310 (10)	0.0178 (8)	0.0177 (8)	0.0057 (8)
C20	0.0269 (9)	0.0345 (11)	0.0394 (11)	0.0123 (8)	0.0124 (8)	0.0128 (9)
C21	0.0246 (9)	0.0259 (9)	0.0333 (10)	0.0017 (7)	0.0023 (7)	0.0072 (7)
C22	0.0265 (8)	0.0154 (7)	0.0256 (8)	0.0007 (6)	0.0067 (7)	0.0019 (6)
C23	0.0253 (8)	0.0118 (7)	0.0184 (7)	−0.0018 (6)	0.0085 (6)	−0.0002 (6)
C24	0.0310 (9)	0.0179 (8)	0.0306 (9)	0.0060 (7)	0.0154 (7)	0.0067 (7)
C25	0.0456 (11)	0.0212 (9)	0.0405 (11)	0.0101 (8)	0.0222 (9)	0.0146 (8)
C26	0.0446 (11)	0.0222 (9)	0.0364 (10)	0.0009 (8)	0.0243 (9)	0.0081 (8)
C27	0.0287 (9)	0.0250 (9)	0.0303 (9)	−0.0010 (7)	0.0155 (7)	0.0016 (7)
C28	0.0250 (8)	0.0173 (8)	0.0231 (8)	0.0007 (6)	0.0083 (6)	0.0018 (6)

Geometric parameters (Å, º) top

Ru1—P2	2.3575 (4)	C18—H18	0.9500
Ru1—P2ⁱ	2.3575 (4)	C18—C19	1.389 (2)
Ru1—P1ⁱ	2.3769 (4)	C15—H15A	0.9900
Ru1—P1	2.3769 (4)	C15—H15B	0.9900
Ru1—Cl1ⁱ	2.5838 (14)	C10—H10	0.9500
Ru1—Cl1	2.5838 (14)	C10—C11	1.390 (2)
Ru1—C1	1.936 (5)	C24—H24	0.9500
Ru1—C1ⁱ	1.936 (5)	C24—C25	1.390 (2)
P2—C23	1.8332 (16)	C13—H13	0.9500
P2—C17	1.8311 (16)	C13—C12	1.382 (3)
P2—C16	1.8414 (16)	C11—H11	0.9500
P1—C3	1.840 (3)	C11—C12	1.381 (3)
P1—C9	1.8337 (16)	C21—H21	0.9500
P1—C15	1.8644 (16)	C21—C22	1.388 (2)
P1—C3A	1.850 (11)	C21—C20	1.390 (3)
Cl1—C1ⁱ	0.670 (4)	C27—H27	0.9500
Cl1—C2ⁱ	0.576 (4)	C27—C26	1.383 (3)
C3—C4	1.3900	C22—H22	0.9500
C3—C8	1.3900	C20—H20	0.9500
C4—H4	0.9500	C20—C19	1.375 (3)
C4—C5	1.3900	C12—H12	0.9500
C5—H5	0.9500	C19—H19	0.9500
C5—C6	1.3900	C25—H25	0.9500
C6—H6	0.9500	C25—C26	1.383 (3)
C6—C7	1.3900	C26—H26	0.9500
C7—H7	0.9500	C1—Cl1ⁱ	0.670 (4)
C7—C8	1.3900	C1—C2	1.190 (5)
C8—H8	0.9500	C2—Cl1ⁱ	0.576 (4)
C23—C28	1.397 (2)	C2—H2	0.9500
C23—C24	1.393 (2)	C3A—C4A	1.397 (12)
C17—C18	1.397 (2)	C3A—C8A	1.402 (11)
C17—C22	1.396 (2)	C4A—H4A	0.9500
C16—H16A	0.9900	C4A—C5A	1.415 (11)
C16—H16B	0.9900	C5A—H5A	0.9500
C16—C15	1.526 (2)	C5A—C6A	1.312 (17)
C9—C14	1.390 (2)	C6A—H6A	0.9500
C9—C10	1.400 (2)	C6A—C7A	1.320 (15)
C14—H14	0.9500	C7A—H7A	0.9500
C14—C13	1.393 (3)	C7A—C8A	1.410 (13)
C28—H28	0.9500	C8A—H8A	0.9500
C28—C27	1.391 (2)

P2ⁱ—Ru1—P2	180.0	C14—C9—P1	121.07 (13)
P2ⁱ—Ru1—P1	98.156 (13)	C14—C9—C10	118.74 (16)
P2—Ru1—P1ⁱ	98.157 (13)	C10—C9—P1	120.17 (13)
P2ⁱ—Ru1—P1ⁱ	81.844 (13)	C9—C14—H14	119.8
P2—Ru1—P1	81.843 (13)	C9—C14—C13	120.38 (18)
P2—Ru1—Cl1ⁱ	94.58 (2)	C13—C14—H14	119.8
P2ⁱ—Ru1—Cl1ⁱ	85.42 (2)	C23—C28—H28	120.0
P2—Ru1—Cl1	85.42 (2)	C27—C28—C23	120.07 (16)
P2ⁱ—Ru1—Cl1	94.58 (2)	C27—C28—H28	120.0
P1ⁱ—Ru1—P1	179.999 (19)	C17—C18—H18	119.6
P1—Ru1—Cl1ⁱ	99.20 (3)	C19—C18—C17	120.84 (17)
P1ⁱ—Ru1—Cl1	99.20 (3)	C19—C18—H18	119.6
P1—Ru1—Cl1	80.80 (3)	P1—C15—H15A	108.9
P1ⁱ—Ru1—Cl1ⁱ	80.80 (3)	P1—C15—H15B	108.9
Cl1—Ru1—Cl1ⁱ	180.00 (4)	C16—C15—P1	113.15 (11)
C1ⁱ—Ru1—P2ⁱ	93.73 (11)	C16—C15—H15A	108.9
C1—Ru1—P2ⁱ	86.27 (11)	C16—C15—H15B	108.9
C1ⁱ—Ru1—P2	86.27 (11)	H15A—C15—H15B	107.8
C1—Ru1—P2	93.73 (11)	C9—C10—H10	119.8
C1—Ru1—P1ⁱ	85.22 (11)	C11—C10—C9	120.46 (17)
C1ⁱ—Ru1—P1	85.22 (11)	C11—C10—H10	119.8
C1—Ru1—P1	94.78 (11)	C23—C24—H24	119.8
C1ⁱ—Ru1—P1ⁱ	94.78 (11)	C25—C24—C23	120.36 (16)
C1ⁱ—Ru1—Cl1	4.43 (12)	C25—C24—H24	119.8
C1—Ru1—Cl1	175.57 (12)	C14—C13—H13	119.8
C1ⁱ—Ru1—Cl1ⁱ	175.57 (12)	C12—C13—C14	120.37 (18)
C1—Ru1—Cl1ⁱ	4.43 (12)	C12—C13—H13	119.8
C1ⁱ—Ru1—C1	180.0	C10—C11—H11	119.9
C23—P2—Ru1	121.50 (5)	C12—C11—C10	120.24 (18)
C23—P2—C16	102.27 (7)	C12—C11—H11	119.9
C17—P2—Ru1	119.70 (5)	C22—C21—H21	119.8
C17—P2—C23	101.62 (7)	C22—C21—C20	120.35 (18)
C17—P2—C16	103.83 (7)	C20—C21—H21	119.8
C16—P2—Ru1	105.41 (5)	C28—C27—H27	119.7
C3—P1—Ru1	127.91 (17)	C26—C27—C28	120.58 (17)
C3—P1—C15	96.22 (18)	C26—C27—H27	119.7
C9—P1—Ru1	116.67 (5)	C17—C22—H22	119.8
C9—P1—C3	99.91 (19)	C21—C22—C17	120.42 (16)
C9—P1—C15	103.66 (8)	C21—C22—H22	119.8
C9—P1—C3A	103.0 (5)	C21—C20—H20	120.1
C15—P1—Ru1	108.57 (5)	C19—C20—C21	119.78 (17)
C3A—P1—Ru1	121.2 (5)	C19—C20—H20	120.1
C3A—P1—C15	101.4 (6)	C13—C12—H12	120.1
C2ⁱ—Cl1—Ru1	158.0 (5)	C11—C12—C13	119.81 (17)
C2ⁱ—Cl1—C1ⁱ	145.2 (7)	C11—C12—H12	120.1
C4—C3—P1	119.8 (2)	C18—C19—H19	119.9
C4—C3—C8	120.0	C20—C19—C18	120.18 (18)
C8—C3—P1	120.2 (2)	C20—C19—H19	119.9
C3—C4—H4	120.0	C24—C25—H25	119.8
C5—C4—C3	120.0	C26—C25—C24	120.43 (17)
C5—C4—H4	120.0	C26—C25—H25	119.8
C4—C5—H5	120.0	C27—C26—H26	120.2
C4—C5—C6	120.0	C25—C26—C27	119.56 (17)
C6—C5—H5	120.0	C25—C26—H26	120.2
C5—C6—H6	120.0	C2—C1—Ru1	177.7 (4)
C7—C6—C5	120.0	Cl1ⁱ—C2—H2	161.3
C7—C6—H6	120.0	C1—C2—H2	180.0
C6—C7—H7	120.0	C4A—C3A—P1	119.6 (9)
C6—C7—C8	120.0	C4A—C3A—C8A	115.4 (8)
C8—C7—H7	120.0	C8A—C3A—P1	122.4 (10)
C3—C8—H8	120.0	C3A—C4A—H4A	120.3
C7—C8—C3	120.0	C3A—C4A—C5A	119.3 (10)
C7—C8—H8	120.0	C5A—C4A—H4A	120.3
C28—C23—P2	118.30 (12)	C4A—C5A—H5A	119.1
C24—C23—P2	122.70 (13)	C6A—C5A—C4A	121.8 (11)
C24—C23—C28	118.99 (15)	C6A—C5A—H5A	119.1
C18—C17—P2	122.66 (13)	C5A—C6A—H6A	119.5
C22—C17—P2	118.88 (12)	C5A—C6A—C7A	121.0 (9)
C22—C17—C18	118.41 (15)	C7A—C6A—H6A	119.5
P2—C16—H16A	109.9	C6A—C7A—H7A	120.3
P2—C16—H16B	109.9	C6A—C7A—C8A	119.5 (9)
H16A—C16—H16B	108.3	C8A—C7A—H7A	120.3
C15—C16—P2	108.75 (11)	C3A—C8A—C7A	121.5 (10)
C15—C16—H16A	109.9	C3A—C8A—H8A	119.2
C15—C16—H16B	109.9	C7A—C8A—H8A	119.2

Ru1—P2—C23—C28	−38.82 (15)	C4—C5—C6—C7	0.0
Ru1—P2—C23—C24	139.91 (13)	C5—C6—C7—C8	0.0
Ru1—P2—C17—C18	125.95 (13)	C6—C7—C8—C3	0.0
Ru1—P2—C17—C22	−56.55 (14)	C8—C3—C4—C5	0.0
Ru1—P2—C16—C15	−51.85 (11)	C23—P2—C17—C18	−97.05 (15)
Ru1—P1—C3—C4	−16.3 (4)	C23—P2—C17—C22	80.45 (14)
Ru1—P1—C3—C8	165.22 (18)	C23—P2—C16—C15	−179.76 (11)
Ru1—P1—C9—C14	87.24 (14)	C23—C28—C27—C26	1.0 (3)
Ru1—P1—C9—C10	−91.31 (13)	C23—C24—C25—C26	0.4 (3)
Ru1—P1—C15—C16	−12.75 (13)	C17—P2—C23—C28	−174.82 (13)
Ru1—P1—C3A—C4A	−34.9 (14)	C17—P2—C23—C24	3.91 (16)
Ru1—P1—C3A—C8A	163.9 (8)	C17—P2—C16—C15	74.82 (12)
P2—Ru1—P1—C3	99.6 (2)	C17—C18—C19—C20	−0.9 (3)
P2ⁱ—Ru1—P1—C3	−80.4 (2)	C16—P2—C23—C28	78.06 (14)
P2ⁱ—Ru1—P1—C9	49.05 (6)	C16—P2—C23—C24	−103.21 (15)
P2—Ru1—P1—C9	−130.95 (6)	C16—P2—C17—C18	8.85 (16)
P2—Ru1—P1—C15	−14.37 (6)	C16—P2—C17—C22	−173.64 (13)
P2ⁱ—Ru1—P1—C15	165.63 (6)	C9—P1—C3—C4	−151.8 (3)
P2ⁱ—Ru1—P1—C3A	−77.8 (7)	C9—P1—C3—C8	29.7 (3)
P2—Ru1—P1—C3A	102.2 (7)	C9—P1—C15—C16	111.93 (12)
P2ⁱ—Ru1—Cl1—C1ⁱ	79.0 (14)	C9—P1—C3A—C4A	−167.6 (11)
P2—Ru1—Cl1—C1ⁱ	−101.0 (14)	C9—P1—C3A—C8A	31.2 (11)
P2ⁱ—Ru1—Cl1—C2ⁱ	89.1 (15)	C9—C14—C13—C12	0.1 (3)
P2—Ru1—Cl1—C2ⁱ	−90.9 (15)	C9—C10—C11—C12	0.1 (3)
P2—Ru1—C1—Cl1ⁱ	101.3 (14)	C14—C9—C10—C11	0.1 (2)
P2ⁱ—Ru1—C1—Cl1ⁱ	−78.7 (14)	C14—C13—C12—C11	0.0 (3)
P2—C23—C28—C27	177.65 (13)	C28—C23—C24—C25	0.4 (3)
P2—C23—C24—C25	−178.28 (15)	C28—C27—C26—C25	−0.2 (3)
P2—C17—C18—C19	178.71 (14)	C18—C17—C22—C21	−0.2 (2)
P2—C17—C22—C21	−177.77 (13)	C15—P1—C3—C4	103.1 (3)
P2—C16—C15—P1	41.29 (14)	C15—P1—C3—C8	−75.4 (3)
P1ⁱ—Ru1—P2—C23	−30.89 (6)	C15—P1—C9—C14	−32.02 (15)
P1—Ru1—P2—C23	149.11 (6)	C15—P1—C9—C10	149.43 (13)
P1—Ru1—P2—C17	−82.46 (6)	C15—P1—C3A—C4A	85.3 (12)
P1ⁱ—Ru1—P2—C17	97.54 (6)	C15—P1—C3A—C8A	−75.9 (10)
P1ⁱ—Ru1—P2—C16	−146.19 (6)	C10—C9—C14—C13	−0.2 (2)
P1—Ru1—P2—C16	33.81 (6)	C10—C11—C12—C13	−0.2 (3)
P1ⁱ—Ru1—Cl1—C1ⁱ	−3.5 (14)	C24—C23—C28—C27	−1.1 (3)
P1—Ru1—Cl1—C1ⁱ	176.5 (14)	C24—C25—C26—C27	−0.5 (3)
P1ⁱ—Ru1—Cl1—C2ⁱ	6.6 (15)	C21—C20—C19—C18	−0.5 (3)
P1—Ru1—Cl1—C2ⁱ	−173.4 (15)	C22—C17—C18—C19	1.2 (3)
P1—Ru1—C1—Cl1ⁱ	−176.6 (14)	C22—C21—C20—C19	1.5 (3)
P1ⁱ—Ru1—C1—Cl1ⁱ	3.4 (14)	C20—C21—C22—C17	−1.2 (3)
P1—C3—C4—C5	−178.5 (4)	C1—Ru1—P2—C23	−116.59 (12)
P1—C3—C8—C7	178.5 (4)	C1ⁱ—Ru1—P2—C23	63.41 (12)
P1—C9—C14—C13	−178.75 (13)	C1—Ru1—P2—C17	11.84 (12)
P1—C9—C10—C11	178.64 (13)	C1ⁱ—Ru1—P2—C17	−168.16 (12)
P1—C3A—C4A—C5A	−172.6 (13)	C1ⁱ—Ru1—P2—C16	−51.89 (12)
P1—C3A—C8A—C7A	169.8 (14)	C1—Ru1—P2—C16	128.11 (12)
Cl1ⁱ—Ru1—P2—C23	−112.23 (7)	C1—Ru1—P1—C3	6.5 (3)
Cl1—Ru1—P2—C23	67.77 (7)	C1ⁱ—Ru1—P1—C3	−173.5 (3)
Cl1ⁱ—Ru1—P2—C17	16.20 (7)	C1—Ru1—P1—C9	135.96 (13)
Cl1—Ru1—P2—C17	−163.80 (7)	C1ⁱ—Ru1—P1—C9	−44.04 (13)
Cl1ⁱ—Ru1—P2—C16	132.47 (6)	C1—Ru1—P1—C15	−107.46 (12)
Cl1—Ru1—P2—C16	−47.53 (6)	C1ⁱ—Ru1—P1—C15	72.54 (12)
Cl1—Ru1—P1—C3	−173.7 (2)	C1ⁱ—Ru1—P1—C3A	−170.9 (7)
Cl1ⁱ—Ru1—P1—C3	6.3 (2)	C1—Ru1—P1—C3A	9.1 (7)
Cl1—Ru1—P1—C9	−44.31 (7)	C1ⁱ—Ru1—Cl1—C2ⁱ	10 (2)
Cl1ⁱ—Ru1—P1—C9	135.69 (7)	C3A—P1—C3—C4	−35 (6)
Cl1—Ru1—P1—C15	72.28 (6)	C3A—P1—C3—C8	147 (6)
Cl1ⁱ—Ru1—P1—C15	−107.72 (6)	C3A—P1—C9—C14	−137.4 (6)
Cl1—Ru1—P1—C3A	−171.1 (7)	C3A—P1—C9—C10	44.1 (6)
Cl1ⁱ—Ru1—P1—C3A	8.9 (7)	C3A—P1—C15—C16	−141.5 (5)
C3—P1—C9—C14	−131.0 (2)	C3A—C4A—C5A—C6A	2.2 (13)
C3—P1—C9—C10	50.5 (2)	C4A—C3A—C8A—C7A	7.8 (14)
C3—P1—C15—C16	−146.3 (2)	C4A—C5A—C6A—C7A	9.1 (17)
C3—P1—C3A—C4A	128 (7)	C5A—C6A—C7A—C8A	−11.4 (18)
C3—P1—C3A—C8A	−33 (5)	C6A—C7A—C8A—C3A	2.7 (15)
C3—C4—C5—C6	0.0	C8A—C3A—C4A—C5A	−10.1 (13)
C4—C3—C8—C7	0.0

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Cu(C₂H)Cl(C₂₆H₂₄P₂)₂]
M_r	958.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	10.92406 (18), 16.0826 (2), 13.2228 (2)
β (°)	105.2553 (17)
V (Å³)	2241.22 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.41 × 0.35 × 0.20

Data collection
Diffractometer	Agilent Xcalibur (Sapphire3, Gemini ultra)
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.912, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	32289, 6470, 5653
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.721

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.072, 1.09
No. of reflections	6470
No. of parameters	293
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.48

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009)., OLEX2 (Dolomanov et al., 2009).

Acknowledgements

This work was supported by FONDECYT through grant No. 3110066. MF thanks the Becaschile Programme (Chile) for support through a postdoctoral fellowship.

References

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