Tetra­ethyl­ammonium trichlorido(η6-p-cymene)ruthenate(II)

Wu, F.-H.; Lu, L.; Duan, T.; Zhang, Q.-F.

doi:10.1107/S1600536809050168

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1695

doi:10.1107/S1600536809050168

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Tetraethylammonium trichlorido(η⁶-p-cymene)ruthenate(II)

Fang-Hui Wu,^a Lude Lu,^a Taike Duan ^b ^* and Qian-Feng Zhang ^b

^aMaterials Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China, and ^bInstitute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma'anshan, Anhui 243002, People's Republic of China
^*Correspondence e-mail: imc@ahut.edu.cn

(Received 2 November 2009; accepted 22 November 2009; online 28 November 2009)

In the title salt, [(C₂H₅)₄N][RuCl₃(C₁₀H₁₄)], the Ru^II atom shows an octahedral coordination in which the aromatic ring of the p-cymene molecule occupies three coordination positions.

Related literature

For bond distances in the [Et₄N]⁺ cation, see: Allen et al. (1987 ). For related structures, see: Arslan et al. (2009a ,b); Solari et al. (2007 ); Vock & Dyson (2007 ); Lalrempuia et al. (2005 ); Liu et al. (2004 ). For the applications of dinuclear [Ru(η⁶-arene)Cl₂]₂ complexes as precursors in inorganic synthesis, see: Le Bozec et al. (1989 ); Quebatte et al. (2005 ).

Experimental

Crystal data

(C₈H₂₀N)[RuCl₃(C₁₀H₁₄)]
M_r = 471.88
Monoclinic, P 2₁ /n
a = 9.5840 (1) Å
b = 22.3797 (2) Å
c = 10.2071 (1) Å
β = 98.668 (1)°
V = 2164.28 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.09 mm⁻¹
T = 296 K
0.43 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.650, T_max = 0.811
21600 measured reflections
4985 independent reflections
4341 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.056
S = 1.02
4985 reflections
215 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ru1—Cl3	2.4216 (5)
Ru1—Cl2	2.4238 (5)
Ru1—Cl1	2.4381 (5)

Cl3—Ru1—Cl2	87.805 (18)
Cl3—Ru1—Cl1	87.763 (19)
Cl2—Ru1—Cl1	87.35 (2)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536809050168/ng2680sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050168/ng2680Isup2.hkl

checkCIF report

Comment top

The general type dinuclear complexes [Ru(η⁶-arene)Cl₂]₂ are well established as useful synthetic precursors in preparative inorganic chemistry (Le Bozec et al. 1989). For example, the commercial [(p-cymene)RuCl₂]₂ was found to display an exceptionally high activity for atom transfer radical addition reactions under mild conditions (Quebatte et al. 2005). Relative to wide investigation of the dinuclear neutral [Ru(η⁶-arene)Cl₂]₂ complexes, mononuclear anions of type [Ru(η⁶-arene)Cl₃] have rarely been described, although the labile chloride ligands in the [Ru(η⁶-arene)Cl₃]^- species can be substituted to result in formation of a series of new complexes with [Ru(η⁶-arene)] fragments (Lalrempuia et al. 2005). It has recently been noted that [Ph₄P][(p-cymene)RuCl₃] was obtained from the reaction of [(p-cymene)RuCl₂]₂ with two equivalents of [Ph₄P]Cl in dichloromethane (Vock & Dyson, 2007). With this idea in mind, in order to isolate trichlororuthenate(II) anion as an effective starting material, we are interested to carry out the similar reaction of [(p-cymene)RuCl₂]₂ with [Et₄N]Cl.H₂O, the mononuclear compound [Et₄N][(p-cymene)RuCl₃] is thus prepared and structurally characterized. In this paper, the initial results of this work are reported.

Complex (I) crystallizes in the monoclinic crystal system, containing two independent ions: [Et₄N]⁺ cation and [RuCl₃(C₁₀H₁₄)]^- anion. The molecular structure of the title compound is depicted in Fig. 1. The coordination geometry of ruthenium is pseudo-octahedral, with an average Ru—Cl bond length is 2.4278 (5) Å and the average Cl—Ru—Cl bond angle is 87.64 (2)°, which are compared with those reported in other related trichlororuthenate(II) complexes such as [Ph₄P][(p-cymene)RuCl₃] (av. Ru—Cl = 2.4450 (11) (5) Å, av. Cl—Ru—Cl = 87.35 (5)°) (Vock & Dyson, 2007), [C₁₄H₁₇N₂S₂][(p-cymene)RuCl₃] (C₁₄H₁₇N₂S₂ = 1,3-bis(thiophen-2-ylmethyl)3,4,5,6- tetrahydropyrimidinium) (av. Ru—Cl = 2.4268 (11) Å, av. Cl—Ru—Cl = 87.10 (3)°) (Arslan et al. 2009a) and [C₁₃H₁₅N₂S₂][(p-cymene)RuCl₃] (C₁₃H₁₅N₂S₂ = 1,3-(2-thienylmethyl)-4,5-dihydroimidazolium) (av. Ru—Cl = 2.4301 (11) Å, av. Cl—Ru—Cl = 87.61 (4)°) (Arslan et al. 2009b). The ruthenium atom exhibits a distorted octahedral coordination with the benzene ring of the p-cymene group formally occupying three of coordination positions and three terminal chloride atoms completing the coordination sphere. The Ru—C(ring) distances span the range 2.1380 (17)—2.1994 (18) Å in the title compound and compare well with those found in other p-cymene-trichlororuthenate(II) compounds (Vock & Dyson, 2007; Arslan et al. 2009a, 2009b). The distance between the centroid of the p-cymene ring and ruthenium is 1.648 (2) Å, which is longer than that reported in other ruthenium compounds with three-chloride ligands (Liu et al., 2004; Solari et al., 2007). The [Et₄N]⁺ cation in the title compound has its expected structure as well as normal distances and angles, which will not be discussed further (Allen et al., 1987).

Related literature top

For bond distances in the [Et₄N]⁺ cation, see: Allen et al. (1987). For related structures, see: Arslan et al. (2009a,b); Solari et al. (2007); Vock & Dyson (2007); Lalrempuia et al. (2005); Liu et al. (2004). For the applications of dinuclear [Ru(η⁶-arene)Cl₂]₂ complexes as precursors in inorganic synthesis, see: Le Bozec et al. (1989); Quebatte et al. (2005).

Experimental top

Treatment of [(p-cymene)RuCl₂]₂ with two equivalents of [Et₄N]Cl.H₂O in a mixed THF/CH₂Cl₂ (1:1) solvent afforded the orange solution. The mixture was stirred for 2 h at room temperature, and then Et₂O (50 ml) was added slowly and the precipitate that formed was filtered off with suction, washed with Et₂O (3 x 10 ml) and dried in vacuo, yielding an orange solid in 92%. Recrystallization from CH₂Cl₂/Et₂O (1:5) gave orange block crystals. Anal. Calcd. for C₁₈H₃₄NCl₃Ru: C, 45.81; H, 7.26; N, 2.97%. Found: C, 45.76; H, 7.23; N, 2.92%.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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. The structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids at the 50% probability level.

Tetraethylammonium trichlorido(η⁶-p-cymene)ruthenate(II) top

Crystal data top

(C₈H₂₀N)[RuCl₃(C₁₀H₁₄)]	F(000) = 976
M_r = 471.88	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9980 reflections
a = 9.5840 (1) Å	θ = 2.2–27.4°
b = 22.3797 (2) Å	µ = 1.09 mm⁻¹
c = 10.2071 (1) Å	T = 296 K
β = 98.668 (1)°	Block, orange
V = 2164.28 (4) Å³	0.43 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4985 independent reflections
Radiation source: fine-focus sealed tube	4341 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
phi and ω scans	θ_max = 27.6°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.650, T_max = 0.811	k = −29→25
21600 measured reflections	l = −11→13

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.056	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0263P)² + 0.6416P] where P = (F_o² + 2F_c²)/3
4985 reflections	(Δ/σ)_max = 0.001
215 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

(C₈H₂₀N)[RuCl₃(C₁₀H₁₄)]	V = 2164.28 (4) Å³
M_r = 471.88	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.5840 (1) Å	µ = 1.09 mm⁻¹
b = 22.3797 (2) Å	T = 296 K
c = 10.2071 (1) Å	0.43 × 0.25 × 0.20 mm
β = 98.668 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4985 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4341 reflections with I > 2σ(I)
T_min = 0.650, T_max = 0.811	R_int = 0.021
21600 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.056	H-atom parameters constrained
S = 1.02	Δρ_max = 0.38 e Å⁻³
4985 reflections	Δρ_min = −0.29 e Å⁻³
215 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	0.825774 (14)	0.078698 (6)	0.112583 (14)	0.03365 (5)
Cl1	0.77065 (6)	0.17844 (2)	0.18611 (7)	0.06579 (16)
Cl2	0.93200 (5)	0.12669 (2)	−0.06104 (5)	0.04993 (12)
Cl3	1.05200 (5)	0.08727 (2)	0.25339 (5)	0.04920 (12)
N1	0.31839 (16)	0.23549 (7)	0.13845 (16)	0.0425 (3)
C1	0.6908 (2)	0.02804 (8)	−0.04218 (19)	0.0441 (4)
C2	0.8053 (2)	−0.00847 (8)	0.01545 (19)	0.0423 (4)
H2	0.8615	−0.0275	−0.0386	0.051*
C3	0.83385 (19)	−0.01594 (8)	0.15289 (19)	0.0410 (4)
H3	0.9099	−0.0397	0.1883	0.049*
C4	0.7509 (2)	0.01140 (8)	0.24034 (19)	0.0428 (4)
C5	0.6385 (2)	0.04798 (9)	0.1819 (2)	0.0463 (4)
H5	0.5831	0.0674	0.2360	0.056*
C6	0.60824 (19)	0.05587 (9)	0.0431 (2)	0.0459 (4)
H6	0.5326	0.0798	0.0077	0.055*
C7	0.6659 (3)	0.03821 (12)	−0.1883 (2)	0.0685 (7)
H7A	0.6319	0.0020	−0.2325	0.103*
H7B	0.7526	0.0499	−0.2172	0.103*
H7C	0.5969	0.0692	−0.2091	0.103*
C8	0.7882 (3)	0.00190 (11)	0.3880 (2)	0.0610 (6)
H8	0.8898	−0.0062	0.4062	0.073*
C9	0.7137 (3)	−0.05322 (14)	0.4288 (3)	0.0890 (9)
H9A	0.7473	−0.0621	0.5202	0.134*
H9B	0.7326	−0.0864	0.3747	0.134*
H9C	0.6138	−0.0460	0.4176	0.134*
C10	0.7606 (5)	0.05526 (15)	0.4702 (3)	0.1227 (15)
H10A	0.8053	0.0899	0.4395	0.184*
H10B	0.7981	0.0480	0.5613	0.184*
H10C	0.6607	0.0620	0.4620	0.184*
C11	0.3550 (2)	0.18162 (9)	0.0607 (2)	0.0576 (5)
H11A	0.4569	0.1793	0.0676	0.069*
H11B	0.3237	0.1460	0.1021	0.069*
C12	0.2929 (3)	0.18074 (11)	−0.0842 (2)	0.0627 (6)
H12A	0.1919	0.1783	−0.0928	0.094*
H12B	0.3283	0.1467	−0.1261	0.094*
H12C	0.3190	0.2166	−0.1259	0.094*
C13	0.1606 (2)	0.23458 (10)	0.1427 (2)	0.0572 (5)
H13A	0.1115	0.2368	0.0525	0.069*
H13B	0.1368	0.1965	0.1790	0.069*
C14	0.1062 (3)	0.28363 (14)	0.2219 (3)	0.0836 (8)
H14A	0.1545	0.2823	0.3114	0.125*
H14B	0.0068	0.2783	0.2218	0.125*
H14C	0.1227	0.3216	0.1832	0.125*
C15	0.3564 (2)	0.29344 (9)	0.0761 (2)	0.0579 (5)
H15A	0.2973	0.2974	−0.0094	0.069*
H15B	0.3331	0.3262	0.1312	0.069*
C16	0.5080 (3)	0.30030 (12)	0.0562 (3)	0.0790 (8)
H16A	0.5672	0.3019	0.1408	0.118*
H16B	0.5186	0.3365	0.0082	0.118*
H16C	0.5349	0.2668	0.0067	0.118*
C17	0.4038 (2)	0.23164 (10)	0.2766 (2)	0.0566 (5)
H17A	0.5030	0.2290	0.2678	0.068*
H17B	0.3906	0.2684	0.3234	0.068*
C18	0.3678 (3)	0.17998 (12)	0.3599 (2)	0.0766 (8)
H18A	0.2708	0.1829	0.3726	0.115*
H18B	0.4274	0.1810	0.4444	0.115*
H18C	0.3824	0.1431	0.3158	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.03190 (8)	0.02950 (8)	0.03954 (8)	−0.00283 (5)	0.00533 (5)	−0.00182 (5)
Cl1	0.0585 (3)	0.0406 (3)	0.0989 (5)	0.0030 (2)	0.0137 (3)	−0.0210 (3)
Cl2	0.0508 (3)	0.0453 (3)	0.0540 (3)	−0.0087 (2)	0.0087 (2)	0.0129 (2)
Cl3	0.0441 (3)	0.0497 (3)	0.0499 (3)	−0.0087 (2)	−0.0057 (2)	−0.0015 (2)
N1	0.0421 (8)	0.0339 (8)	0.0505 (9)	−0.0038 (6)	0.0039 (7)	0.0003 (7)
C1	0.0442 (10)	0.0453 (10)	0.0416 (10)	−0.0154 (8)	0.0022 (8)	−0.0011 (8)
C2	0.0455 (10)	0.0344 (9)	0.0487 (11)	−0.0097 (8)	0.0131 (8)	−0.0094 (8)
C3	0.0425 (10)	0.0290 (9)	0.0506 (10)	−0.0036 (7)	0.0046 (8)	0.0001 (7)
C4	0.0476 (10)	0.0392 (10)	0.0427 (10)	−0.0125 (8)	0.0098 (8)	−0.0011 (8)
C5	0.0388 (10)	0.0467 (11)	0.0571 (12)	−0.0088 (8)	0.0193 (9)	−0.0090 (9)
C6	0.0317 (9)	0.0445 (10)	0.0598 (12)	−0.0040 (8)	0.0017 (8)	0.0009 (9)
C7	0.0750 (16)	0.0813 (17)	0.0453 (12)	−0.0296 (13)	−0.0041 (11)	0.0054 (11)
C8	0.0694 (15)	0.0704 (15)	0.0428 (11)	−0.0186 (12)	0.0074 (10)	0.0022 (10)
C9	0.107 (2)	0.093 (2)	0.0583 (15)	−0.0324 (17)	−0.0146 (15)	0.0351 (15)
C10	0.228 (5)	0.098 (2)	0.0498 (16)	−0.030 (3)	0.047 (2)	−0.0173 (16)
C11	0.0643 (14)	0.0416 (11)	0.0652 (14)	0.0036 (10)	0.0047 (11)	−0.0064 (10)
C12	0.0642 (14)	0.0671 (15)	0.0575 (13)	−0.0073 (11)	0.0116 (11)	−0.0101 (11)
C13	0.0472 (11)	0.0541 (12)	0.0696 (14)	−0.0064 (10)	0.0060 (10)	0.0012 (11)
C14	0.0657 (16)	0.098 (2)	0.093 (2)	0.0031 (15)	0.0288 (14)	−0.0178 (16)
C15	0.0601 (13)	0.0395 (11)	0.0749 (15)	−0.0028 (9)	0.0124 (11)	0.0111 (10)
C16	0.0641 (15)	0.0775 (18)	0.098 (2)	−0.0149 (13)	0.0197 (14)	0.0261 (15)
C17	0.0574 (13)	0.0534 (12)	0.0559 (12)	−0.0111 (10)	−0.0021 (10)	−0.0020 (10)
C18	0.0853 (18)	0.0824 (18)	0.0569 (14)	−0.0217 (14)	−0.0058 (13)	0.0169 (13)

Geometric parameters (Å, º) top

Ru1—C5	2.1390 (17)	C9—H9A	0.9600
Ru1—C3	2.1568 (17)	C9—H9B	0.9600
Ru1—C6	2.1598 (18)	C9—H9C	0.9600
Ru1—C4	2.1829 (18)	C10—H10A	0.9600
Ru1—C2	2.1837 (17)	C10—H10B	0.9600
Ru1—C1	2.1994 (18)	C10—H10C	0.9600
Ru1—Cl3	2.4216 (5)	C11—C12	1.509 (3)
Ru1—Cl2	2.4238 (5)	C11—H11A	0.9700
Ru1—Cl1	2.4381 (5)	C11—H11B	0.9700
N1—C15	1.513 (2)	C12—H12A	0.9600
N1—C11	1.513 (3)	C12—H12B	0.9600
N1—C13	1.520 (2)	C12—H12C	0.9600
N1—C17	1.522 (3)	C13—C14	1.503 (3)
C1—C6	1.407 (3)	C13—H13A	0.9700
C1—C2	1.423 (3)	C13—H13B	0.9700
C1—C7	1.492 (3)	C14—H14A	0.9600
C2—C3	1.398 (3)	C14—H14B	0.9600
C2—H2	0.9300	C14—H14C	0.9600
C3—C4	1.420 (3)	C15—C16	1.505 (3)
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.412 (3)	C15—H15B	0.9700
C4—C8	1.511 (3)	C16—H16A	0.9600
C5—C6	1.413 (3)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C6—H6	0.9300	C17—C18	1.506 (3)
C7—H7A	0.9600	C17—H17A	0.9700
C7—H7B	0.9600	C17—H17B	0.9700
C7—H7C	0.9600	C18—H18A	0.9600
C8—C10	1.505 (4)	C18—H18B	0.9600
C8—C9	1.515 (3)	C18—H18C	0.9600
C8—H8	0.9800

C5—Ru1—C3	68.23 (7)	C1—C6—H6	119.5
C5—Ru1—C6	38.38 (8)	C5—C6—H6	119.5
C3—Ru1—C6	80.53 (7)	Ru1—C6—H6	130.5
C5—Ru1—C4	38.11 (8)	C1—C7—H7A	109.5
C3—Ru1—C4	38.20 (7)	C1—C7—H7B	109.5
C6—Ru1—C4	69.20 (7)	H7A—C7—H7B	109.5
C5—Ru1—C2	80.83 (7)	C1—C7—H7C	109.5
C3—Ru1—C2	37.58 (7)	H7A—C7—H7C	109.5
C6—Ru1—C2	67.89 (7)	H7B—C7—H7C	109.5
C4—Ru1—C2	68.89 (7)	C10—C8—C4	114.1 (2)
C5—Ru1—C1	68.90 (7)	C10—C8—C9	111.2 (2)
C3—Ru1—C1	68.36 (7)	C4—C8—C9	109.79 (18)
C6—Ru1—C1	37.66 (7)	C10—C8—H8	107.1
C4—Ru1—C1	82.12 (7)	C4—C8—H8	107.1
C2—Ru1—C1	37.87 (7)	C9—C8—H8	107.1
C5—Ru1—Cl3	123.36 (6)	C8—C9—H9A	109.5
C3—Ru1—Cl3	87.79 (5)	C8—C9—H9B	109.5
C6—Ru1—Cl3	161.29 (6)	H9A—C9—H9B	109.5
C4—Ru1—Cl3	92.61 (5)	C8—C9—H9C	109.5
C2—Ru1—Cl3	110.56 (5)	H9A—C9—H9C	109.5
C1—Ru1—Cl3	147.57 (6)	H9B—C9—H9C	109.5
C5—Ru1—Cl2	148.21 (6)	C8—C10—H10A	109.5
C3—Ru1—Cl2	124.59 (5)	C8—C10—H10B	109.5
C6—Ru1—Cl2	110.85 (6)	H10A—C10—H10B	109.5
C4—Ru1—Cl2	162.66 (5)	C8—C10—H10C	109.5
C2—Ru1—Cl2	94.75 (5)	H10A—C10—H10C	109.5
C1—Ru1—Cl2	88.26 (5)	H10B—C10—H10C	109.5
Cl3—Ru1—Cl2	87.805 (18)	C12—C11—N1	115.85 (18)
C5—Ru1—Cl1	87.77 (5)	C12—C11—H11A	108.3
C3—Ru1—Cl1	147.52 (5)	N1—C11—H11A	108.3
C6—Ru1—Cl1	94.26 (6)	C12—C11—H11B	108.3
C4—Ru1—Cl1	109.99 (5)	N1—C11—H11B	108.3
C2—Ru1—Cl1	161.60 (5)	H11A—C11—H11B	107.4
C1—Ru1—Cl1	124.18 (6)	C11—C12—H12A	109.5
Cl3—Ru1—Cl1	87.763 (19)	C11—C12—H12B	109.5
Cl2—Ru1—Cl1	87.35 (2)	H12A—C12—H12B	109.5
C15—N1—C11	111.91 (16)	C11—C12—H12C	109.5
C15—N1—C13	109.08 (15)	H12A—C12—H12C	109.5
C11—N1—C13	108.33 (15)	H12B—C12—H12C	109.5
C15—N1—C17	107.95 (15)	C14—C13—N1	115.65 (19)
C11—N1—C17	107.80 (16)	C14—C13—H13A	108.4
C13—N1—C17	111.80 (16)	N1—C13—H13A	108.4
C6—C1—C2	117.97 (17)	C14—C13—H13B	108.4
C6—C1—C7	122.1 (2)	N1—C13—H13B	108.4
C2—C1—C7	119.9 (2)	H13A—C13—H13B	107.4
C6—C1—Ru1	69.65 (10)	C13—C14—H14A	109.5
C2—C1—Ru1	70.46 (10)	C13—C14—H14B	109.5
C7—C1—Ru1	128.89 (14)	H14A—C14—H14B	109.5
C3—C2—C1	120.37 (17)	C13—C14—H14C	109.5
C3—C2—Ru1	70.17 (10)	H14A—C14—H14C	109.5
C1—C2—Ru1	71.66 (10)	H14B—C14—H14C	109.5
C3—C2—H2	119.8	C16—C15—N1	116.26 (18)
C1—C2—H2	119.8	C16—C15—H15A	108.2
Ru1—C2—H2	131.1	N1—C15—H15A	108.2
C2—C3—C4	122.40 (18)	C16—C15—H15B	108.2
C2—C3—Ru1	72.26 (10)	N1—C15—H15B	108.2
C4—C3—Ru1	71.90 (10)	H15A—C15—H15B	107.4
C2—C3—H3	118.8	C15—C16—H16A	109.5
C4—C3—H3	118.8	C15—C16—H16B	109.5
Ru1—C3—H3	129.7	H16A—C16—H16B	109.5
C5—C4—C3	116.60 (17)	C15—C16—H16C	109.5
C5—C4—C8	123.66 (18)	H16A—C16—H16C	109.5
C3—C4—C8	119.71 (19)	H16B—C16—H16C	109.5
C5—C4—Ru1	69.26 (10)	C18—C17—N1	115.44 (17)
C3—C4—Ru1	69.90 (10)	C18—C17—H17A	108.4
C8—C4—Ru1	130.04 (13)	N1—C17—H17A	108.4
C4—C5—C6	121.64 (17)	C18—C17—H17B	108.4
C4—C5—Ru1	72.63 (10)	N1—C17—H17B	108.4
C6—C5—Ru1	71.61 (10)	H17A—C17—H17B	107.5
C4—C5—H5	119.2	C17—C18—H18A	109.5
C6—C5—H5	119.2	C17—C18—H18B	109.5
Ru1—C5—H5	129.0	H18A—C18—H18B	109.5
C1—C6—C5	121.00 (18)	C17—C18—H18C	109.5
C1—C6—Ru1	72.70 (10)	H18A—C18—H18C	109.5
C5—C6—Ru1	70.02 (10)	H18B—C18—H18C	109.5

C5—Ru1—C1—C6	28.91 (12)	C2—Ru1—C4—C3	27.98 (11)
C3—Ru1—C1—C6	102.96 (12)	C1—Ru1—C4—C3	64.77 (12)
C4—Ru1—C1—C6	65.97 (12)	Cl3—Ru1—C4—C3	−83.08 (11)
C2—Ru1—C1—C6	131.49 (17)	Cl2—Ru1—C4—C3	7.9 (2)
Cl3—Ru1—C1—C6	148.37 (10)	Cl1—Ru1—C4—C3	−171.65 (10)
Cl2—Ru1—C1—C6	−128.49 (11)	C5—Ru1—C4—C8	−117.1 (2)
Cl1—Ru1—C1—C6	−42.89 (13)	C3—Ru1—C4—C8	112.5 (2)
C5—Ru1—C1—C2	−102.58 (12)	C6—Ru1—C4—C8	−146.1 (2)
C3—Ru1—C1—C2	−28.52 (11)	C2—Ru1—C4—C8	140.4 (2)
C6—Ru1—C1—C2	−131.49 (17)	C1—Ru1—C4—C8	177.2 (2)
C4—Ru1—C1—C2	−65.52 (11)	Cl3—Ru1—C4—C8	29.4 (2)
Cl3—Ru1—C1—C2	16.88 (16)	Cl2—Ru1—C4—C8	120.4 (2)
Cl2—Ru1—C1—C2	100.02 (10)	Cl1—Ru1—C4—C8	−59.2 (2)
Cl1—Ru1—C1—C2	−174.37 (9)	C3—C4—C5—C6	1.4 (3)
C5—Ru1—C1—C7	144.2 (2)	C8—C4—C5—C6	179.53 (18)
C3—Ru1—C1—C7	−141.7 (2)	Ru1—C4—C5—C6	54.47 (16)
C6—Ru1—C1—C7	115.3 (3)	C3—C4—C5—Ru1	−53.09 (14)
C4—Ru1—C1—C7	−178.7 (2)	C8—C4—C5—Ru1	125.06 (18)
C2—Ru1—C1—C7	−113.2 (3)	C3—Ru1—C5—C4	30.46 (11)
Cl3—Ru1—C1—C7	−96.3 (2)	C6—Ru1—C5—C4	133.10 (17)
Cl2—Ru1—C1—C7	−13.2 (2)	C2—Ru1—C5—C4	67.33 (11)
Cl1—Ru1—C1—C7	72.5 (2)	C1—Ru1—C5—C4	104.70 (12)
C6—C1—C2—C3	−0.2 (3)	Cl3—Ru1—C5—C4	−41.32 (12)
C7—C1—C2—C3	176.88 (17)	Cl2—Ru1—C5—C4	151.52 (10)
Ru1—C1—C2—C3	52.52 (15)	Cl1—Ru1—C5—C4	−127.16 (11)
C6—C1—C2—Ru1	−52.68 (15)	C3—Ru1—C5—C6	−102.64 (12)
C7—C1—C2—Ru1	124.36 (17)	C4—Ru1—C5—C6	−133.10 (17)
C5—Ru1—C2—C3	−66.02 (12)	C2—Ru1—C5—C6	−65.77 (12)
C6—Ru1—C2—C3	−103.69 (12)	C1—Ru1—C5—C6	−28.40 (11)
C4—Ru1—C2—C3	−28.40 (11)	Cl3—Ru1—C5—C6	−174.42 (9)
C1—Ru1—C2—C3	−133.30 (16)	Cl2—Ru1—C5—C6	18.41 (17)
Cl3—Ru1—C2—C3	56.28 (11)	Cl1—Ru1—C5—C6	99.74 (11)
Cl2—Ru1—C2—C3	145.71 (10)	C2—C1—C6—C5	0.3 (3)
Cl1—Ru1—C2—C3	−118.41 (17)	C7—C1—C6—C5	−176.69 (18)
C5—Ru1—C2—C1	67.27 (11)	Ru1—C1—C6—C5	−52.79 (16)
C3—Ru1—C2—C1	133.30 (16)	C2—C1—C6—Ru1	53.07 (14)
C6—Ru1—C2—C1	29.60 (11)	C7—C1—C6—Ru1	−123.90 (18)
C4—Ru1—C2—C1	104.89 (12)	C4—C5—C6—C1	−0.9 (3)
Cl3—Ru1—C2—C1	−170.43 (9)	Ru1—C5—C6—C1	54.01 (16)
Cl2—Ru1—C2—C1	−81.00 (10)	C4—C5—C6—Ru1	−54.94 (16)
Cl1—Ru1—C2—C1	14.9 (2)	C5—Ru1—C6—C1	−133.41 (17)
C1—C2—C3—C4	0.7 (3)	C3—Ru1—C6—C1	−66.68 (12)
Ru1—C2—C3—C4	53.89 (15)	C4—Ru1—C6—C1	−104.60 (12)
C1—C2—C3—Ru1	−53.20 (15)	C2—Ru1—C6—C1	−29.76 (11)
C5—Ru1—C3—C2	103.75 (13)	Cl3—Ru1—C6—C1	−118.74 (17)
C6—Ru1—C3—C2	65.86 (12)	Cl2—Ru1—C6—C1	56.84 (12)
C4—Ru1—C3—C2	134.14 (17)	Cl1—Ru1—C6—C1	145.63 (11)
C1—Ru1—C3—C2	28.73 (11)	C3—Ru1—C6—C5	66.73 (12)
Cl3—Ru1—C3—C2	−128.80 (11)	C4—Ru1—C6—C5	28.82 (11)
Cl2—Ru1—C3—C2	−43.00 (13)	C2—Ru1—C6—C5	103.65 (13)
Cl1—Ru1—C3—C2	148.87 (9)	C1—Ru1—C6—C5	133.41 (17)
C5—Ru1—C3—C4	−30.39 (11)	Cl3—Ru1—C6—C5	14.7 (2)
C6—Ru1—C3—C4	−68.28 (12)	Cl2—Ru1—C6—C5	−169.74 (10)
C2—Ru1—C3—C4	−134.14 (17)	Cl1—Ru1—C6—C5	−80.96 (11)
C1—Ru1—C3—C4	−105.41 (12)	C5—C4—C8—C10	−32.8 (3)
Cl3—Ru1—C3—C4	97.05 (11)	C3—C4—C8—C10	145.3 (2)
Cl2—Ru1—C3—C4	−177.15 (9)	Ru1—C4—C8—C10	57.4 (3)
Cl1—Ru1—C3—C4	14.72 (17)	C5—C4—C8—C9	92.9 (3)
C2—C3—C4—C5	−1.3 (3)	C3—C4—C8—C9	−89.0 (3)
Ru1—C3—C4—C5	52.77 (14)	Ru1—C4—C8—C9	−176.91 (19)
C2—C3—C4—C8	−179.49 (17)	C15—N1—C11—C12	−55.0 (2)
Ru1—C3—C4—C8	−125.45 (17)	C13—N1—C11—C12	65.3 (2)
C2—C3—C4—Ru1	−54.04 (15)	C17—N1—C11—C12	−173.51 (18)
C3—Ru1—C4—C5	−130.42 (17)	C15—N1—C13—C14	−60.7 (3)
C6—Ru1—C4—C5	−29.01 (11)	C11—N1—C13—C14	177.2 (2)
C2—Ru1—C4—C5	−102.45 (12)	C17—N1—C13—C14	58.6 (3)
C1—Ru1—C4—C5	−65.65 (12)	C11—N1—C15—C16	−56.5 (3)
Cl3—Ru1—C4—C5	146.49 (10)	C13—N1—C15—C16	−176.3 (2)
Cl2—Ru1—C4—C5	−122.52 (17)	C17—N1—C15—C16	62.0 (3)
Cl1—Ru1—C4—C5	57.93 (11)	C15—N1—C17—C18	173.4 (2)
C5—Ru1—C4—C3	130.42 (17)	C11—N1—C17—C18	−65.5 (3)
C6—Ru1—C4—C3	101.42 (12)	C13—N1—C17—C18	53.4 (3)

Experimental details

Crystal data
Chemical formula	(C₈H₂₀N)[RuCl₃(C₁₀H₁₄)]
M_r	471.88
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.5840 (1), 22.3797 (2), 10.2071 (1)
β (°)	98.668 (1)
V (Å³)	2164.28 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.09
Crystal size (mm)	0.43 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.650, 0.811
No. of measured, independent and observed [I > 2σ(I)] reflections	21600, 4985, 4341
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.056, 1.02
No. of reflections	4985
No. of parameters	215
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.29

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ru1—Cl3	2.4216 (5)	Ru1—Cl1	2.4381 (5)
Ru1—Cl2	2.4238 (5)

Cl3—Ru1—Cl2	87.805 (18)	Cl2—Ru1—Cl1	87.35 (2)
Cl3—Ru1—Cl1	87.763 (19)

Acknowledgements

This project was supported by the Program for New Century Excellent Talents in Universities of China (NCET-06–0556 and NCET-08–0618).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Arslan, H., VanDerveer, D., Özdemir, İ., Gürbüz, N., Gök, Y. & Çetinkaya, B. (2009a). Acta Cryst. E65, m111–m112. Web of Science CSD CrossRef IUCr Journals Google Scholar
Arslan, H., VanDerveer, D., Özdemir, İ., Gürbüz, N., Gök, Y. & Çetinkaya, B. (2009b). Acta Cryst. E65, m165–m166. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lalrempuia, R., Kollipara, M. R., Carroll, P. J., Yap, G. P. A. & Kreisel, K. A. (2005). J. Organomet. Chem. 690, 3990–3996. Web of Science CSD CrossRef CAS Google Scholar
Le Bozec, H., Touchard, D. & Dixneuf, P. H. (1989). Adv. Organomet. Chem. 29, 163–247. CAS Google Scholar
Liu, L., Zhang, Q.-F. & Leung, W.-H. (2004). Acta Cryst. E60, m506–m508. Web of Science CSD CrossRef IUCr Journals Google Scholar
Quebatte, L., Solari, E., Scopelliti, R. & Severin, K. (2005). Organometallics, 24, 1404–1406. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Solari, E., Antonijevic, S., Gauthier, S., Scopelliti, R. & Severin, R. (2007). Eur. J. Inorg. Chem. pp. 367–371. Web of Science CSD CrossRef Google Scholar
Vock, C. A. & Dyson, P. J. (2007). Z. Anorg. Allg. Chem. 633, 640–642. Web of Science CSD CrossRef CAS Google Scholar