Dichlorido(dimethyl sulfoxide-κS)(η6-mesitylene)ruthenium(II)

Oelkers, B.; Finger, L.H.; Sundermeyer, J.

doi:10.1107/S160053681100314X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page m319

doi:10.1107/S160053681100314X

Open

access

Dichlorido(dimethyl sulfoxide-κS)(η⁶-mesitylene)ruthenium(II)

Benjamin Oelkers,^a Lars Hendrik Finger ^a and Jörg Sundermeyer ^a ^*

^aPhilipps-Universität Marburg, Fachbereich Chemie, Hans-Meerwein-Strasse, 35032 Marburg, Germany
^*Correspondence e-mail: jsu@staff.uni-marburg.de

(Received 18 November 2010; accepted 24 January 2011; online 12 February 2011)

The title compound, [RuCl₂(C₉H₁₂)(C₂H₆OS)], features a planar [maximum deviation = 0.0075 (17) Å] η⁶-bound mesitylene ligand and a dimethyl sulfoxide ligand coordinated via the S atom. The overall complex geometry about the Ru(II) atom is best described as a piano-stool configuration.

Related literature

For similar complexes of the type [RuCl₂(DMSO)(arene)], see: Ogata et al. (1970 ) (arene = benzene); Chandra et al. (2002 ) (arene = p-cymene); Beasley et al. (1993 ) (arene = 1,4,9,10-tetrahydroanthracene); Haquette et al. (2008 ) (arene = 9,10-dihydroanthracene); Sadler et al. (2005 ) (arene = 2-chloro-N-(2-phenylethyl)acetamide).

Experimental

Crystal data

[RuCl₂(C₉H₁₂)(C₂H₆OS)]
M_r = 370.28
Monoclinic, P 2₁ /n
a = 8.1184 (4) Å
b = 22.9372 (13) Å
c = 8.3417 (4) Å
β = 116.443 (3)°
V = 1390.82 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.64 mm⁻¹
T = 100 K
0.24 × 0.15 × 0.09 mm

Data collection

Stoe IPDS 2T diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.630, T_max = 0.994
9737 measured reflections
2935 independent reflections
2753 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.017
wR(F²) = 0.044
S = 1.04
2935 reflections
150 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

C1—Ru1	2.2209 (15)
C2—Ru1	2.2162 (15)
C3—Ru1	2.2219 (16)
C4—Ru1	2.2097 (16)
C5—Ru1	2.2160 (17)
C6—Ru1	2.1978 (15)
S1—Ru1	2.3399 (4)
Cl1—Ru1	2.4097 (4)
Cl2—Ru1	2.3963 (4)

S1—Ru1—Cl2	85.030 (14)
S1—Ru1—Cl1	84.567 (14)
Cl2—Ru1—Cl1	88.636 (15)

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg, 2007 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100314X/kj2168sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100314X/kj2168Isup2.hkl

checkCIF report

Comment top

Complexes of the type [{RuCl₂(arene)}₂] are valuable starting materials for the preparation of ruthenium(II) complexes because they allow facile ligand substitution. During our investigations concerning the arene substitution behaviour of such complexes, we found that [{RuCl₂(C₆H₃Me₃)}₂] readily reacts with dimethylsulfoxide, yielding the monomeric title compound [RuCl₂(DMSO)(C₆H₃Me₃)]. Similar reactivity has been reported for the corresponding benzene and p-cymene complexes (Ogata et al., 1970; Chandra et al., 2002).

The overall complex geometry of the title compound is best described as a piano-stool configuration. Another possible description is that of an octahedral d⁶ low-spin complex with the arene ligand occupying three fac-oriented coordination sites. The angles between the monodentate chloro and DMSO ligands are thus close to 90° (Table 1). The planar, η⁶-bound mesitylene ligand shows almost equal Ru–C distances of 2.1978 (15) to 2.2219 (16) Å. Dimethylsulfoxide is coordinated via sulfur as usual for complexes without sufficient steric bulk to force O-coordination. All numerical parameters concerning the molecular geometry are similar to those observed for the corresponding p-cymene complex (Chandra et al., 2002).

Related literature top

For similar complexes of the type [RuCl₂(DMSO)(arene)], see: Ogata et al. (1970) (arene = benzene); Chandra et al. (2002) (arene = p-cymene); Beasley et al. (1993) (arene = 1,4,9,10-tetrahydroanthracene); Haquette et al. (2008) (arene = 9,10-dihydroanthracene); Sadler et al. (2005) (arene = 2-chloro-N-(2-phenylethyl)acetamide).

Experimental top

[{RuCl₂(C₆H₃Me₃)}₂] (175 mg, 0.30 mmol) was dissolved in DMSO (12 ml). The solution was heated to 100 °C for 45 min and a small amount of ruthenium black was removed by filtration. The dark red solution was concentrated in vacuo until the formation of crystals was observed. The product was isolated by filtration and dried in vacuo. A second crop of material was obtained from the mother liquor by layering with toluene. Yield: 150 mg (68%) of red crystals. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a saturated DMSO solution.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are shown for 50% probability.

Dichlorido(dimethyl sulfoxide-κS)(η⁶-mesitylene)ruthenium(II) top

Crystal data top

[RuCl₂(C₉H₁₂)(C₂H₆OS)]	F(000) = 744
M_r = 370.28	D_x = 1.768 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 16004 reflections
a = 8.1184 (4) Å	θ = 1.9–27.2°
b = 22.9372 (13) Å	µ = 1.64 mm⁻¹
c = 8.3417 (4) Å	T = 100 K
β = 116.443 (3)°	Block, light red
V = 1390.82 (12) Å³	0.24 × 0.15 × 0.09 mm
Z = 4

Data collection top

Stoe IPDS 2T diffractometer	2935 independent reflections
Radiation source: fine-focus sealed tube	2753 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.7°, θ_min = 2.9°
rotation method scans	h = −10→10
Absorption correction: multi-scan (Blessing, 1995)	k = −28→29
T_min = 0.630, T_max = 0.994	l = −9→10
9737 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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.044	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0208P)² + 0.742P] where P = (F_o² + 2F_c²)/3
2935 reflections	(Δ/σ)_max = 0.002
150 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

[RuCl₂(C₉H₁₂)(C₂H₆OS)]	V = 1390.82 (12) Å³
M_r = 370.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.1184 (4) Å	µ = 1.64 mm⁻¹
b = 22.9372 (13) Å	T = 100 K
c = 8.3417 (4) Å	0.24 × 0.15 × 0.09 mm
β = 116.443 (3)°

Data collection top

Stoe IPDS 2T diffractometer	2935 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	2753 reflections with I > 2σ(I)
T_min = 0.630, T_max = 0.994	R_int = 0.051
9737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.017	0 restraints
wR(F²) = 0.044	H-atom parameters constrained
S = 1.04	Δρ_max = 0.42 e Å⁻³
2935 reflections	Δρ_min = −0.71 e Å⁻³
150 parameters

Special details top

Experimental. Anal. calc. for C₁₁H₁₈Cl₂ORuS (370.29 g/mol) C 35.68, H 4.90%; found C 35.42, H 4.98%. ¹H NMR (250 MHz, DMSO-d₆, 300 K) δ = 2.14 (s, 9H, CH₃), 2.54 (s, 6H, DMSO), 5.46 (s, 3H, CH) p.p.m.; ¹³C NMR (75 MHz, DMSO-d₆, 300 K) δ = 18.2 (CH₃), 40.4 (DMSO), 82.0 (CH), 104.8 (CCH₃) p.p.m.. IR (neat, ATR) ν = 3063 w, 3024 m, 2963 w, 2931 w, 1525 m, 1447 m, 1408 m, 1377 m, 1303 m, 1286 m, 1105 s, 1034 m, 1008 versus, 983 s, 971 m, 932 m, 905 m, 887 m, 721 m, 680 m, 641 m, 507 w, 415 s cm^-1.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.1365 (2)	0.08700 (8)	−0.1389 (2)	0.0176 (4)
C2	0.2204 (2)	0.03526 (7)	−0.0475 (2)	0.0172 (3)
H2	0.2639	0.0074	−0.1039	0.021*
C3	0.2406 (2)	0.02437 (7)	0.1282 (2)	0.0168 (3)
C4	0.1758 (2)	0.06592 (7)	0.2106 (2)	0.0162 (3)
H4	0.1889	0.0588	0.3279	0.019*
C5	0.0910 (2)	0.11842 (7)	0.1211 (2)	0.0161 (3)
C6	0.0741 (2)	0.12862 (7)	−0.0535 (2)	0.0168 (3)
H6	0.0201	0.1639	−0.1137	0.020*
C7	0.1190 (3)	0.09819 (10)	−0.3227 (2)	0.0283 (4)
H7A	0.2138	0.0762	−0.3392	0.042*
H7B	0.1348	0.1399	−0.3369	0.042*
H7C	−0.0030	0.0858	−0.4122	0.042*
C8	0.3318 (3)	−0.03050 (8)	0.2244 (3)	0.0257 (4)
H8A	0.3877	−0.0238	0.3539	0.039*
H8B	0.4273	−0.0420	0.1891	0.039*
H8C	0.2400	−0.0616	0.1930	0.039*
C9	0.0139 (2)	0.16108 (8)	0.2056 (3)	0.0244 (4)
H9A	−0.1136	0.1506	0.1753	0.037*
H9B	0.0174	0.2004	0.1609	0.037*
H9C	0.0875	0.1602	0.3359	0.037*
C10	0.5260 (2)	0.16583 (7)	0.5447 (2)	0.0178 (3)
H10A	0.5907	0.1970	0.6298	0.027*
H10B	0.6034	0.1309	0.5755	0.027*
H10C	0.4105	0.1570	0.5500	0.027*
C11	0.7007 (2)	0.21278 (7)	0.3628 (2)	0.0169 (3)
H11A	0.6939	0.2315	0.2544	0.025*
H11B	0.7841	0.1793	0.3935	0.025*
H11C	0.7470	0.2408	0.4618	0.025*
O1	0.35990 (15)	0.24130 (5)	0.28238 (15)	0.0164 (2)
S1	0.47771 (5)	0.188752 (16)	0.32416 (5)	0.01120 (8)
Cl1	0.65955 (5)	0.066716 (17)	0.30769 (5)	0.01704 (9)
Cl2	0.50102 (5)	0.159381 (18)	−0.04032 (5)	0.01767 (9)
Ru1	0.364774 (16)	0.110410 (5)	0.124893 (15)	0.01033 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0100 (8)	0.0246 (9)	0.0132 (8)	−0.0059 (6)	0.0007 (6)	−0.0026 (6)
C2	0.0133 (8)	0.0158 (7)	0.0200 (8)	−0.0048 (6)	0.0052 (6)	−0.0089 (6)
C3	0.0126 (7)	0.0115 (7)	0.0229 (8)	−0.0046 (6)	0.0048 (6)	−0.0011 (6)
C4	0.0138 (8)	0.0175 (8)	0.0167 (8)	−0.0050 (6)	0.0062 (6)	0.0005 (6)
C5	0.0102 (8)	0.0152 (7)	0.0219 (8)	−0.0033 (6)	0.0063 (7)	−0.0044 (6)
C6	0.0075 (7)	0.0165 (8)	0.0200 (8)	−0.0007 (6)	0.0003 (6)	0.0032 (6)
C7	0.0219 (10)	0.0449 (11)	0.0126 (8)	−0.0066 (8)	0.0029 (7)	−0.0010 (8)
C8	0.0215 (9)	0.0144 (8)	0.0358 (10)	−0.0009 (7)	0.0079 (8)	0.0028 (7)
C9	0.0184 (9)	0.0226 (9)	0.0368 (10)	−0.0024 (7)	0.0165 (8)	−0.0075 (8)
C10	0.0231 (9)	0.0162 (8)	0.0126 (7)	−0.0017 (7)	0.0067 (7)	−0.0004 (6)
C11	0.0140 (8)	0.0169 (8)	0.0189 (8)	−0.0046 (6)	0.0065 (6)	−0.0047 (6)
O1	0.0164 (6)	0.0114 (5)	0.0179 (5)	0.0031 (4)	0.0044 (5)	−0.0005 (4)
S1	0.01161 (18)	0.00975 (17)	0.01084 (17)	−0.00026 (13)	0.00373 (14)	−0.00063 (13)
Cl1	0.01246 (19)	0.01451 (18)	0.01854 (19)	0.00243 (14)	0.00185 (15)	−0.00313 (14)
Cl2	0.01695 (19)	0.0227 (2)	0.01450 (18)	−0.00450 (15)	0.00802 (15)	−0.00160 (14)
Ru1	0.00945 (8)	0.00984 (7)	0.01029 (8)	−0.00034 (4)	0.00314 (5)	−0.00124 (4)

Geometric parameters (Å, º) top

C1—C2	1.411 (2)	C7—H7C	0.9800
C1—C6	1.413 (3)	C8—H8A	0.9800
C1—C7	1.498 (2)	C8—H8B	0.9800
C1—Ru1	2.2209 (15)	C8—H8C	0.9800
C2—C3	1.423 (2)	C9—H9A	0.9800
C2—Ru1	2.2162 (15)	C9—H9B	0.9800
C2—H2	0.9500	C9—H9C	0.9800
C3—C4	1.407 (2)	C10—S1	1.7807 (16)
C3—C8	1.499 (2)	C10—H10A	0.9800
C3—Ru1	2.2219 (16)	C10—H10B	0.9800
C4—C5	1.423 (2)	C10—H10C	0.9800
C4—Ru1	2.2097 (16)	C11—S1	1.7792 (17)
C4—H4	0.9500	C11—H11A	0.9800
C5—C6	1.420 (2)	C11—H11B	0.9800
C5—C9	1.496 (2)	C11—H11C	0.9800
C5—Ru1	2.2160 (17)	O1—S1	1.4806 (11)
C6—Ru1	2.1978 (15)	S1—Ru1	2.3399 (4)
C6—H6	0.9500	Cl1—Ru1	2.4097 (4)
C7—H7A	0.9800	Cl2—Ru1	2.3963 (4)
C7—H7B	0.9800

C2—C1—C6	119.41 (15)	S1—C10—H10A	109.5
C2—C1—C7	120.01 (17)	S1—C10—H10B	109.5
C6—C1—C7	120.56 (17)	H10A—C10—H10B	109.5
C2—C1—Ru1	71.28 (9)	S1—C10—H10C	109.5
C6—C1—Ru1	70.47 (9)	H10A—C10—H10C	109.5
C7—C1—Ru1	129.03 (12)	H10B—C10—H10C	109.5
C1—C2—C3	120.71 (15)	S1—C11—H11A	109.5
C1—C2—Ru1	71.64 (9)	S1—C11—H11B	109.5
C3—C2—Ru1	71.52 (9)	H11A—C11—H11B	109.5
C1—C2—H2	119.6	S1—C11—H11C	109.5
C3—C2—H2	119.6	H11A—C11—H11C	109.5
Ru1—C2—H2	129.7	H11B—C11—H11C	109.5
C4—C3—C2	119.20 (15)	O1—S1—C11	106.80 (8)
C4—C3—C8	120.71 (16)	O1—S1—C10	107.79 (8)
C2—C3—C8	120.09 (16)	C11—S1—C10	99.56 (8)
C4—C3—Ru1	71.02 (9)	O1—S1—Ru1	116.76 (5)
C2—C3—Ru1	71.09 (9)	C11—S1—Ru1	114.32 (6)
C8—C3—Ru1	129.33 (12)	C10—S1—Ru1	110.09 (6)
C3—C4—C5	121.05 (16)	C6—Ru1—C4	67.42 (6)
C3—C4—Ru1	71.97 (10)	C6—Ru1—C5	37.53 (6)
C5—C4—Ru1	71.49 (10)	C4—Ru1—C5	37.50 (6)
C3—C4—H4	119.5	C6—Ru1—C2	67.06 (6)
C5—C4—H4	119.5	C4—Ru1—C2	66.92 (6)
Ru1—C4—H4	129.6	C5—Ru1—C2	79.51 (6)
C6—C5—C4	118.76 (15)	C6—Ru1—C1	37.29 (7)
C6—C5—C9	120.37 (16)	C4—Ru1—C1	79.38 (6)
C4—C5—C9	120.83 (16)	C5—Ru1—C1	67.47 (6)
C6—C5—Ru1	70.54 (9)	C2—Ru1—C1	37.08 (6)
C4—C5—Ru1	71.01 (9)	C6—Ru1—C3	79.68 (6)
C9—C5—Ru1	132.43 (12)	C4—Ru1—C3	37.01 (6)
C1—C6—C5	120.86 (15)	C5—Ru1—C3	67.42 (6)
C1—C6—Ru1	72.24 (9)	C2—Ru1—C3	37.40 (6)
C5—C6—Ru1	71.93 (9)	C1—Ru1—C3	67.33 (6)
C1—C6—H6	119.6	C6—Ru1—S1	107.34 (5)
C5—C6—H6	119.6	C4—Ru1—S1	103.51 (4)
Ru1—C6—H6	128.6	C5—Ru1—S1	91.13 (4)
C1—C7—H7A	109.5	C2—Ru1—S1	170.04 (5)
C1—C7—H7B	109.5	C1—Ru1—S1	141.22 (5)
H7A—C7—H7B	109.5	C3—Ru1—S1	135.20 (5)
C1—C7—H7C	109.5	C6—Ru1—Cl2	98.80 (5)
H7A—C7—H7C	109.5	C4—Ru1—Cl2	165.32 (4)
H7B—C7—H7C	109.5	C5—Ru1—Cl2	132.05 (5)
C3—C8—H8A	109.5	C2—Ru1—Cl2	103.74 (5)
C3—C8—H8B	109.5	C1—Ru1—Cl2	86.49 (5)
H8A—C8—H8B	109.5	C3—Ru1—Cl2	138.75 (5)
C3—C8—H8C	109.5	S1—Ru1—Cl2	85.030 (14)
H8A—C8—H8C	109.5	C6—Ru1—Cl1	166.37 (4)
H8B—C8—H8C	109.5	C4—Ru1—Cl1	103.89 (4)
C5—C9—H9A	109.5	C5—Ru1—Cl1	138.64 (5)
C5—C9—H9B	109.5	C2—Ru1—Cl1	100.16 (5)
H9A—C9—H9B	109.5	C1—Ru1—Cl1	132.98 (5)
C5—C9—H9C	109.5	C3—Ru1—Cl1	87.19 (4)
H9A—C9—H9C	109.5	S1—Ru1—Cl1	84.567 (14)
H9B—C9—H9C	109.5	Cl2—Ru1—Cl1	88.636 (15)

C6—C1—C2—C3	0.8 (2)	C9—C5—Ru1—Cl1	86.88 (18)
C7—C1—C2—C3	179.05 (15)	C1—C2—Ru1—C6	29.22 (10)
Ru1—C1—C2—C3	54.15 (14)	C3—C2—Ru1—C6	−103.49 (11)
C6—C1—C2—Ru1	−53.39 (13)	C1—C2—Ru1—C4	103.39 (11)
C7—C1—C2—Ru1	124.90 (15)	C3—C2—Ru1—C4	−29.32 (10)
C1—C2—C3—C4	0.0 (2)	C1—C2—Ru1—C5	66.34 (10)
Ru1—C2—C3—C4	54.18 (13)	C3—C2—Ru1—C5	−66.37 (10)
C1—C2—C3—C8	−179.36 (15)	C3—C2—Ru1—C1	−132.71 (15)
Ru1—C2—C3—C8	−125.15 (15)	C1—C2—Ru1—C3	132.71 (15)
C1—C2—C3—Ru1	−54.21 (14)	C1—C2—Ru1—Cl2	−64.65 (10)
C2—C3—C4—C5	−0.1 (2)	C3—C2—Ru1—Cl2	162.64 (9)
C8—C3—C4—C5	179.26 (15)	C1—C2—Ru1—Cl1	−155.73 (9)
Ru1—C3—C4—C5	54.15 (14)	C3—C2—Ru1—Cl1	71.55 (9)
C2—C3—C4—Ru1	−54.21 (13)	C2—C1—Ru1—C6	−132.10 (15)
C8—C3—C4—Ru1	125.12 (15)	C7—C1—Ru1—C6	114.0 (2)
C3—C4—C5—C6	−0.6 (2)	C2—C1—Ru1—C4	−65.58 (10)
Ru1—C4—C5—C6	53.79 (13)	C6—C1—Ru1—C4	66.52 (10)
C3—C4—C5—C9	176.92 (15)	C7—C1—Ru1—C4	−179.48 (19)
Ru1—C4—C5—C9	−128.72 (15)	C2—C1—Ru1—C5	−102.83 (11)
C3—C4—C5—Ru1	−54.37 (14)	C6—C1—Ru1—C5	29.27 (10)
C2—C1—C6—C5	−1.4 (2)	C7—C1—Ru1—C5	143.28 (19)
C7—C1—C6—C5	−179.70 (15)	C6—C1—Ru1—C2	132.10 (15)
Ru1—C1—C6—C5	−55.19 (13)	C7—C1—Ru1—C2	−113.9 (2)
C2—C1—C6—Ru1	53.77 (13)	C2—C1—Ru1—C3	−28.92 (10)
C7—C1—C6—Ru1	−124.51 (15)	C6—C1—Ru1—C3	103.18 (11)
C4—C5—C6—C1	1.3 (2)	C7—C1—Ru1—C3	−142.81 (19)
C9—C5—C6—C1	−176.18 (15)	C2—C1—Ru1—S1	−163.99 (8)
Ru1—C5—C6—C1	55.34 (13)	C6—C1—Ru1—S1	−31.89 (13)
C4—C5—C6—Ru1	−54.01 (13)	C7—C1—Ru1—S1	82.11 (19)
C9—C5—C6—Ru1	128.48 (15)	C2—C1—Ru1—Cl2	118.42 (10)
C1—C6—Ru1—C4	−102.51 (11)	C6—C1—Ru1—Cl2	−109.48 (9)
C5—C6—Ru1—C4	29.64 (9)	C7—C1—Ru1—Cl2	4.53 (17)
C1—C6—Ru1—C5	−132.15 (14)	C2—C1—Ru1—Cl1	33.57 (12)
C1—C6—Ru1—C2	−29.07 (10)	C6—C1—Ru1—Cl1	165.67 (8)
C5—C6—Ru1—C2	103.08 (11)	C7—C1—Ru1—Cl1	−80.32 (19)
C5—C6—Ru1—C1	132.15 (14)	C4—C3—Ru1—C6	−66.00 (10)
C1—C6—Ru1—C3	−65.95 (10)	C2—C3—Ru1—C6	65.54 (10)
C5—C6—Ru1—C3	66.20 (10)	C8—C3—Ru1—C6	179.40 (18)
C1—C6—Ru1—S1	159.72 (9)	C2—C3—Ru1—C4	131.54 (14)
C5—C6—Ru1—S1	−68.13 (9)	C8—C3—Ru1—C4	−114.6 (2)
C1—C6—Ru1—Cl2	72.21 (10)	C4—C3—Ru1—C5	−28.87 (9)
C5—C6—Ru1—Cl2	−155.64 (9)	C2—C3—Ru1—C5	102.67 (11)
C1—C6—Ru1—Cl1	−50.2 (2)	C8—C3—Ru1—C5	−143.47 (18)
C5—C6—Ru1—Cl1	81.9 (2)	C4—C3—Ru1—C2	−131.54 (14)
C3—C4—Ru1—C6	103.26 (11)	C8—C3—Ru1—C2	113.9 (2)
C5—C4—Ru1—C6	−29.67 (9)	C4—C3—Ru1—C1	−102.85 (11)
C3—C4—Ru1—C5	132.92 (14)	C2—C3—Ru1—C1	28.69 (10)
C3—C4—Ru1—C2	29.61 (9)	C8—C3—Ru1—C1	142.55 (18)
C5—C4—Ru1—C2	−103.31 (11)	C4—C3—Ru1—S1	38.27 (12)
C3—C4—Ru1—C1	66.25 (10)	C2—C3—Ru1—S1	169.81 (8)
C5—C4—Ru1—C1	−66.67 (10)	C8—C3—Ru1—S1	−76.33 (18)
C5—C4—Ru1—C3	−132.92 (14)	C4—C3—Ru1—Cl2	−157.62 (8)
C3—C4—Ru1—S1	−153.33 (9)	C2—C3—Ru1—Cl2	−26.08 (13)
C5—C4—Ru1—S1	73.75 (9)	C8—C3—Ru1—Cl2	87.78 (17)
C3—C4—Ru1—Cl2	82.2 (2)	C4—C3—Ru1—Cl1	117.67 (9)
C5—C4—Ru1—Cl2	−50.7 (2)	C2—C3—Ru1—Cl1	−110.79 (9)
C3—C4—Ru1—Cl1	−65.67 (9)	C8—C3—Ru1—Cl1	3.07 (16)
C5—C4—Ru1—Cl1	161.41 (8)	O1—S1—Ru1—C6	−11.73 (8)
C4—C5—Ru1—C6	131.39 (14)	C11—S1—Ru1—C6	−137.40 (8)
C9—C5—Ru1—C6	−113.8 (2)	C10—S1—Ru1—C6	111.55 (8)
C6—C5—Ru1—C4	−131.39 (14)	O1—S1—Ru1—C4	−81.94 (7)
C9—C5—Ru1—C4	114.8 (2)	C11—S1—Ru1—C4	152.39 (8)
C6—C5—Ru1—C2	−65.82 (10)	C10—S1—Ru1—C4	41.34 (8)
C4—C5—Ru1—C2	65.57 (10)	O1—S1—Ru1—C5	−46.16 (7)
C9—C5—Ru1—C2	−179.61 (18)	C11—S1—Ru1—C5	−171.83 (8)
C6—C5—Ru1—C1	−29.10 (10)	C10—S1—Ru1—C5	77.11 (8)
C4—C5—Ru1—C1	102.29 (11)	O1—S1—Ru1—C1	7.87 (9)
C9—C5—Ru1—C1	−142.89 (19)	C11—S1—Ru1—C1	−117.80 (9)
C6—C5—Ru1—C3	−102.88 (10)	C10—S1—Ru1—C1	131.14 (9)
C4—C5—Ru1—C3	28.51 (10)	O1—S1—Ru1—C3	−104.49 (8)
C9—C5—Ru1—C3	143.33 (19)	C11—S1—Ru1—C3	129.85 (9)
C6—C5—Ru1—S1	117.62 (9)	C10—S1—Ru1—C3	18.79 (9)
C4—C5—Ru1—S1	−110.99 (9)	O1—S1—Ru1—Cl2	85.96 (6)
C9—C5—Ru1—S1	3.83 (17)	C11—S1—Ru1—Cl2	−39.71 (6)
C6—C5—Ru1—Cl2	33.29 (11)	C10—S1—Ru1—Cl2	−150.77 (6)
C4—C5—Ru1—Cl2	164.69 (7)	O1—S1—Ru1—Cl1	175.05 (6)
C9—C5—Ru1—Cl2	−80.50 (18)	C11—S1—Ru1—Cl1	49.39 (6)
C6—C5—Ru1—Cl1	−159.32 (8)	C10—S1—Ru1—Cl1	−61.67 (6)
C4—C5—Ru1—Cl1	−27.93 (12)

Experimental details

Crystal data
Chemical formula	[RuCl₂(C₉H₁₂)(C₂H₆OS)]
M_r	370.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	8.1184 (4), 22.9372 (13), 8.3417 (4)
β (°)	116.443 (3)
V (Å³)	1390.82 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.64
Crystal size (mm)	0.24 × 0.15 × 0.09

Data collection
Diffractometer	Stoe IPDS 2T diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.630, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	9737, 2935, 2753
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.632

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.017, 0.044, 1.04
No. of reflections	2935
No. of parameters	150
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.71

Computer programs: X-AREA (Stoe & Cie, 2001), X-RED (Stoe & Cie, 2001), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2007), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

C1—Ru1	2.2209 (15)	C6—Ru1	2.1978 (15)
C2—Ru1	2.2162 (15)	S1—Ru1	2.3399 (4)
C3—Ru1	2.2219 (16)	Cl1—Ru1	2.4097 (4)
C4—Ru1	2.2097 (16)	Cl2—Ru1	2.3963 (4)
C5—Ru1	2.2160 (17)

S1—Ru1—Cl2	85.030 (14)	Cl2—Ru1—Cl1	88.636 (15)
S1—Ru1—Cl1	84.567 (14)

Acknowledgements

Routine data collection was performed by the XRD service department (Dr K. Harms, G. Geiseler, R. Riedel) of the Chemistry Department, Philipps University, and is gratefully acknowledged.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Beasley, T. J., Brost, R. D., Chu, C. K., Grundy, S. L. & Stobart, S. R. (1993). Organometallics, 12, 4599–4606. CSD CrossRef CAS Web of Science Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Brandenburg, K. (2007). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Chandra, M., Pandey, D. S., Puerta, M. C. & Valerga, P. (2002). Acta Cryst. E58, m28–m29. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Haquette, P., Talbi, B., Canaguier, S., Dagorne, S., Fosse, C., Martel, A., Jaouen, G. & Salmain, M. (2008). Tetrahedron Lett. 49, 4670–4673. Web of Science CSD CrossRef CAS Google Scholar
Ogata, I., Iwata, R. & Ikeda, Y. (1970). Tetrahedron Lett. 34, 3011–3014. CrossRef Google Scholar
Sadler, P., Chen, H., Parsons, S. & Messenger, D. (2005). Private communication (refcode: KANXUT). CCDC, Cambridge, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany. Google Scholar