trans-Di-μ-carbonyl-bis­{carbon­yl[η5-2,3,4,5-tetra­methyl-1-(2-thien­yl)cyclo­penta­dien­yl]ruthenium(I)}(Ru—Ru)

Ma, Z.-H.; Dong, G.-Y.; Liu, X.-H.; Lin, J.

doi:10.1107/S1600536809026063

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m894

doi:10.1107/S1600536809026063

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trans-Di-μ-carbonyl-bis{carbonyl[η⁵-2,3,4,5-tetramethyl-1-(2-thienyl)cyclopentadienyl]ruthenium(I)}(Ru—Ru)

Zhi-Hong Ma,^a,^b Gui-Ying Dong,^c Xiao-Huan Liu ^a and Jin Lin ^a ^*

^aCollege of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang 050016, People's Republic of China, ^bCollege of Basic Medicine, Hebei Medical University, Shijiazhuang 050017, People's Republic of China, and ^cCollege of Chemical Engineering and Biotechnology, Hebei Polytechnic University, Tangshan 063009, People's Republic of China
^*Correspondence e-mail: tswlhx@126.com

(Received 7 June 2009; accepted 5 July 2009; online 11 July 2009)

The title compound, [Ru₂(C₁₃H₁₅S)₂(CO)₄], is a centrosymmetric binuclear metal–carbonyl complex containing an Ru—Ru single bond [2.7511 (8) Å]. Each Ru^I atom is coordinated by two bridging carbonyl ligands, one terminal carbonyl ligand and one η⁵-cyclopentadienyl group. The complex has a trans conformation and the two cyclopentadienyl ring planes are parallel. The crystal structure involves weak C—H⋯O hydrogen bonds.

Related literature

For general background to substituted cyclopentadienyl–metal complexes, see: Arndt (2002 ); Bailey et al. (1978 ); King (1976 ); Möhring & Coville (2006 ). For the crystal structures of related ruthenium complexes, see: Schumann et al. (2002 ).

Experimental

Crystal data

[Ru₂(C₁₃H₁₅S)₂(CO)₄]
M_r = 720.82
Triclinic, $[P \overline 1]$
a = 8.269 (2) Å
b = 8.899 (3) Å
c = 10.056 (3) Å
α = 81.826 (4)°
β = 76.083 (5)°
γ = 82.876 (5)°
V = 707.9 (4) Å³
Z = 1
Mo Kα radiation
μ = 1.25 mm⁻¹
T = 273 K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.835, T_max = 0.885
3667 measured reflections
2493 independent reflections
2431 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.100
S = 1.03
2493 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Selected bond lengths (Å)

Ru1—C1	2.018 (3)
Ru1—C1ⁱ	2.048 (3)
Ru1—C2	1.862 (3)
Ru1—C3	2.246 (3)
Ru1—C4	2.291 (3)
Ru1—C5	2.302 (3)
Ru1—C6	2.282 (3)
Ru1—C7	2.217 (3)
Symmetry code: (i) -x, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱⁱ	0.93	2.60	3.335 (5)	136
C14—H14B⋯O2ⁱ	0.96	2.58	3.319 (4)	134
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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/S1600536809026063/hy2205sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026063/hy2205Isup2.hkl

checkCIF report

Comment top

Cyclopentadienyl metal complexes have been extensively investigated since ferrocene has been discovered. Replacement of the hydrogen atoms by other substituents alters both the steric and electronic influences of the H⁵-cyclopentadienyl ring, resulting in differing reactivity and stability of the substituted cyclopentadienyl metal complexes (Arndt, 2002; King, 1976). Especially for metallocene polymerization catalysts, the steric and electronic effects of the substituents on cyclopentadienyl ring greatly influence catalytic activity (Bailey et al., 1978; Möhring & Coville, 2006).

The title compound, [Ru₂(C₁₃H₁₅S)₂(CO)₄], is a centrosymmetric binuclear metal–carbonyl complex containing an Ru—Ru single bond. As shown in Fig. 1, the cyclopentadienyl ring of the organic ligand coordinates to the Ru^I atom (Table 1), while the thienyl group acting as a substituent is uncoordinated. The Ru1—Cg1 distance is 1.911 (3) Å, where Cg1 is the centroid of the cyclopentadienyl ring. The Ru—Ru bond distance is 2.7511 (8) Å and agrees with that observed in the analogous structure [2.751 (1) Å] (Schumann et al., 2002). The two cyclopentadienyl rings are parallel by virtue of the center of symmetry. The complex has a trans conformation, with two bridging carbonyl ligands and two terminal carbonyl ligands. The crystal packing is stabilized by weak C—H···O hydrogen bonds (Table 2).

Related literature top

For general background to substituted cyclopentadienyl–metal complexes, see: Arndt (2002); Bailey et al. (1978); King (1976); Möhring & Coville (2006). For the crystal structures of related ruthenium complexes, see: Schumann et al. (2002).

Experimental top

A solution of 1-(2-thienyl)-2,3,4,5-tetramethylcyclopentadiene (0.288 g, 1.41 mmol) and Ru₃(CO)₁₂ (0.30 g, 0.47 mmol) in xylene (30 ml) was refluxed for 12 h. The solvent was removed under vacuum and the residue was chromatographed on an Al₂O₃ column using petroleum ether/dichloromethane (volume ratio = 1:3) as eluent. The red band was collected, and after several days red crystals were obtained (yield 0.142 g, 27.9%). Analysis calculated for C₃₀H₃₀O₄Ru₂S₂: C 49.99, H 4.19%; found: C 49.94, H 4.21%.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) -x, 1-y, 1-z.]

trans-Di-µ-carbonyl-bis{carbonyl[η⁵-2,3,4,5-tetramethyl-1-(2- thienyl)cyclopentadienyl]ruthenium(I)}(Ru—Ru) top

Crystal data top

[Ru₂(C₁₃H₁₅S)₂(CO)₄]	Z = 1
M_r = 720.82	F(000) = 362
Triclinic, P1	D_x = 1.691 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.269 (2) Å	Cell parameters from 1002 reflections
b = 8.899 (3) Å	θ = 4.5–22.2°
c = 10.056 (3) Å	µ = 1.25 mm⁻¹
α = 81.826 (4)°	T = 273 K
β = 76.083 (5)°	Block, red
γ = 82.876 (5)°	0.15 × 0.12 × 0.10 mm
V = 707.9 (4) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	2493 independent reflections
Radiation source: fine-focus sealed tube	2431 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.835, T_max = 0.885	k = −10→10
3667 measured reflections	l = −11→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.09P)² + 0.0001P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2493 reflections	Δρ_max = 0.53 e Å⁻³
173 parameters	Δρ_min = −0.63 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (3)

Crystal data top

[Ru₂(C₁₃H₁₅S)₂(CO)₄]	γ = 82.876 (5)°
M_r = 720.82	V = 707.9 (4) Å³
Triclinic, P1	Z = 1
a = 8.269 (2) Å	Mo Kα radiation
b = 8.899 (3) Å	µ = 1.25 mm⁻¹
c = 10.056 (3) Å	T = 273 K
α = 81.826 (4)°	0.15 × 0.12 × 0.10 mm
β = 76.083 (5)°

Data collection top

Bruker SMART APEX CCD diffractometer	2493 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2431 reflections with I > 2σ(I)
T_min = 0.835, T_max = 0.885	R_int = 0.016
3667 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	Δρ_max = 0.53 e Å⁻³
2493 reflections	Δρ_min = −0.63 e Å⁻³
173 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ru1	−0.01450 (2)	0.40733 (2)	0.623212 (18)	0.02438 (17)
S1	0.40230 (13)	0.12210 (13)	0.86000 (11)	0.0622 (3)
O1	−0.1870 (5)	0.1684 (4)	0.5431 (3)	0.0836 (10)
O2	0.2945 (3)	0.3491 (3)	0.4011 (3)	0.0510 (6)
C1	0.1653 (3)	0.4142 (3)	0.4472 (3)	0.0314 (6)
C2	−0.1213 (4)	0.2620 (4)	0.5688 (3)	0.0440 (8)
C3	0.1390 (3)	0.2962 (3)	0.7731 (3)	0.0298 (6)
C4	0.1719 (3)	0.4517 (3)	0.7456 (3)	0.0302 (6)
C5	0.0180 (4)	0.5430 (3)	0.7921 (3)	0.0327 (6)
C6	−0.1104 (4)	0.4436 (3)	0.8499 (3)	0.0337 (6)
C7	−0.0383 (4)	0.2915 (4)	0.8363 (3)	0.0319 (6)
C8	0.2643 (4)	0.1630 (3)	0.7537 (3)	0.0329 (6)
C9	0.2855 (4)	0.0553 (4)	0.6641 (4)	0.0452 (8)
H9	0.2217	0.0550	0.5996	0.054*
C10	0.4219 (5)	−0.0577 (4)	0.6847 (5)	0.0606 (10)
H10	0.4556	−0.1393	0.6328	0.073*
C11	0.4936 (5)	−0.0364 (5)	0.7814 (5)	0.0657 (11)
H11	0.5834	−0.0992	0.8050	0.079*
C12	0.3402 (4)	0.5088 (4)	0.6853 (3)	0.0423 (7)
H12A	0.3276	0.6035	0.6280	0.063*
H12B	0.4104	0.4352	0.6308	0.063*
H12C	0.3905	0.5244	0.7583	0.063*
C13	−0.0043 (5)	0.7128 (4)	0.7947 (4)	0.0500 (8)
H13A	−0.0294	0.7352	0.8885	0.075*
H13B	−0.0946	0.7558	0.7523	0.075*
H13C	0.0970	0.7558	0.7449	0.075*
C14	−0.2858 (4)	0.4923 (5)	0.9167 (3)	0.0504 (9)
H14A	−0.3539	0.4098	0.9259	0.076*
H14B	−0.3272	0.5783	0.8610	0.076*
H14C	−0.2900	0.5202	1.0063	0.076*
C15	−0.1239 (4)	0.1515 (4)	0.8928 (3)	0.0439 (8)
H15A	−0.1240	0.1282	0.9890	0.066*
H15B	−0.0661	0.0681	0.8443	0.066*
H15C	−0.2372	0.1677	0.8818	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.0253 (2)	0.0278 (2)	0.0202 (2)	−0.00256 (12)	−0.00515 (12)	−0.00352 (12)
S1	0.0550 (6)	0.0681 (7)	0.0699 (7)	0.0124 (5)	−0.0345 (5)	−0.0105 (5)
O1	0.121 (3)	0.074 (2)	0.071 (2)	−0.060 (2)	−0.0269 (19)	−0.0075 (16)
O2	0.0391 (13)	0.0660 (17)	0.0375 (13)	0.0190 (12)	−0.0024 (10)	−0.0029 (11)
C1	0.0284 (14)	0.0381 (15)	0.0274 (14)	0.0025 (11)	−0.0075 (11)	−0.0057 (12)
C2	0.056 (2)	0.0469 (18)	0.0334 (17)	−0.0202 (16)	−0.0128 (14)	−0.0008 (14)
C3	0.0289 (14)	0.0367 (14)	0.0258 (14)	−0.0035 (11)	−0.0108 (11)	−0.0023 (11)
C4	0.0323 (14)	0.0360 (15)	0.0242 (13)	−0.0065 (11)	−0.0093 (11)	−0.0020 (11)
C5	0.0397 (15)	0.0379 (16)	0.0235 (14)	0.0006 (12)	−0.0123 (11)	−0.0088 (12)
C6	0.0344 (15)	0.0460 (17)	0.0212 (13)	−0.0002 (13)	−0.0070 (11)	−0.0070 (12)
C7	0.0310 (14)	0.0416 (17)	0.0211 (14)	−0.0071 (12)	−0.0033 (11)	0.0017 (12)
C8	0.0322 (14)	0.0367 (15)	0.0290 (14)	−0.0025 (11)	−0.0091 (11)	0.0013 (12)
C9	0.0489 (19)	0.0351 (17)	0.0497 (19)	0.0096 (14)	−0.0128 (15)	−0.0076 (14)
C10	0.056 (2)	0.045 (2)	0.077 (3)	0.0101 (17)	−0.009 (2)	−0.0149 (19)
C11	0.046 (2)	0.058 (2)	0.086 (3)	0.0160 (18)	−0.019 (2)	0.005 (2)
C12	0.0353 (16)	0.0540 (19)	0.0393 (17)	−0.0175 (14)	−0.0081 (13)	−0.0001 (14)
C13	0.068 (2)	0.0416 (18)	0.0459 (19)	0.0010 (15)	−0.0186 (16)	−0.0176 (15)
C14	0.0393 (18)	0.073 (2)	0.0341 (17)	0.0036 (16)	0.0012 (14)	−0.0136 (17)
C15	0.0439 (18)	0.0474 (19)	0.0400 (17)	−0.0165 (15)	−0.0109 (14)	0.0095 (14)

Geometric parameters (Å, º) top

Ru1—C1	2.018 (3)	C6—C7	1.421 (4)
Ru1—C1ⁱ	2.048 (3)	C6—C14	1.484 (4)
Ru1—C2	1.862 (3)	C7—C15	1.483 (4)
Ru1—C3	2.246 (3)	C8—C9	1.374 (4)
Ru1—C4	2.291 (3)	C9—C10	1.449 (5)
Ru1—C5	2.302 (3)	C9—H9	0.9300
Ru1—C6	2.282 (3)	C10—C11	1.300 (6)
Ru1—C7	2.217 (3)	C10—H10	0.9300
Ru1—Ru1ⁱ	2.7511 (8)	C11—H11	0.9300
S1—C11	1.718 (4)	C12—H12A	0.9600
S1—C8	1.718 (3)	C12—H12B	0.9600
O1—C2	1.139 (4)	C12—H12C	0.9600
O2—C1	1.173 (3)	C13—H13A	0.9600
C1—Ru1ⁱ	2.048 (3)	C13—H13B	0.9600
C3—C4	1.420 (4)	C13—H13C	0.9600
C3—C7	1.454 (4)	C14—H14A	0.9600
C3—C8	1.476 (4)	C14—H14B	0.9600
C4—C5	1.436 (4)	C14—H14C	0.9600
C4—C12	1.499 (4)	C15—H15A	0.9600
C5—C6	1.428 (4)	C15—H15B	0.9600
C5—C13	1.502 (4)	C15—H15C	0.9600

C2—Ru1—C1	92.57 (13)	C6—C5—C13	124.5 (3)
C2—Ru1—C1ⁱ	93.27 (14)	C4—C5—C13	126.8 (3)
C1—Ru1—C1ⁱ	94.85 (10)	C6—C5—Ru1	71.09 (15)
C2—Ru1—C7	93.67 (13)	C4—C5—Ru1	71.36 (15)
C1—Ru1—C7	135.88 (11)	C13—C5—Ru1	128.18 (19)
C1ⁱ—Ru1—C7	128.26 (11)	C7—C6—C5	107.8 (2)
C2—Ru1—C3	110.26 (13)	C7—C6—C14	126.8 (3)
C1—Ru1—C3	99.57 (11)	C5—C6—C14	125.4 (3)
C1ⁱ—Ru1—C3	151.61 (11)	C7—C6—Ru1	69.11 (15)
C7—Ru1—C3	38.01 (10)	C5—C6—Ru1	72.61 (15)
C2—Ru1—C6	113.52 (13)	C14—C6—Ru1	125.5 (2)
C1—Ru1—C6	151.57 (11)	C6—C7—C3	108.2 (3)
C1ⁱ—Ru1—C6	94.73 (11)	C6—C7—C15	125.8 (3)
C7—Ru1—C6	36.80 (10)	C3—C7—C15	125.7 (3)
C3—Ru1—C6	61.88 (10)	C6—C7—Ru1	74.10 (16)
C2—Ru1—C4	146.49 (13)	C3—C7—Ru1	72.09 (15)
C1—Ru1—C4	91.03 (11)	C15—C7—Ru1	125.5 (2)
C1ⁱ—Ru1—C4	119.61 (11)	C9—C8—C3	129.5 (3)
C7—Ru1—C4	61.83 (10)	C9—C8—S1	111.3 (2)
C3—Ru1—C4	36.45 (10)	C3—C8—S1	119.1 (2)
C6—Ru1—C4	61.06 (10)	C8—C9—C10	110.1 (3)
C2—Ru1—C5	149.83 (12)	C8—C9—H9	125.0
C1—Ru1—C5	116.93 (11)	C10—C9—H9	125.0
C1ⁱ—Ru1—C5	90.57 (11)	C11—C10—C9	114.9 (4)
C7—Ru1—C5	61.24 (11)	C11—C10—H10	122.6
C3—Ru1—C5	61.10 (10)	C9—C10—H10	122.6
C6—Ru1—C5	36.30 (11)	C10—C11—S1	111.7 (3)
C4—Ru1—C5	36.45 (10)	C10—C11—H11	124.1
C2—Ru1—Ru1ⁱ	94.32 (10)	S1—C11—H11	124.1
C1—Ru1—Ru1ⁱ	47.87 (8)	C4—C12—H12A	109.5
C1ⁱ—Ru1—Ru1ⁱ	46.97 (8)	C4—C12—H12B	109.5
C7—Ru1—Ru1ⁱ	170.96 (8)	H12A—C12—H12B	109.5
C3—Ru1—Ru1ⁱ	140.96 (7)	C4—C12—H12C	109.5
C6—Ru1—Ru1ⁱ	134.95 (8)	H12A—C12—H12C	109.5
C4—Ru1—Ru1ⁱ	112.39 (7)	H12B—C12—H12C	109.5
C5—Ru1—Ru1ⁱ	109.85 (8)	C5—C13—H13A	109.5
C11—S1—C8	91.94 (18)	C5—C13—H13B	109.5
O2—C1—Ru1	139.3 (2)	H13A—C13—H13B	109.5
O2—C1—Ru1ⁱ	135.5 (2)	C5—C13—H13C	109.5
Ru1—C1—Ru1ⁱ	85.15 (10)	H13A—C13—H13C	109.5
O1—C2—Ru1	175.9 (3)	H13B—C13—H13C	109.5
C4—C3—C7	107.5 (2)	C6—C14—H14A	109.5
C4—C3—C8	126.3 (2)	C6—C14—H14B	109.5
C7—C3—C8	126.0 (3)	H14A—C14—H14B	109.5
C4—C3—Ru1	73.49 (15)	C6—C14—H14C	109.5
C7—C3—Ru1	69.90 (15)	H14A—C14—H14C	109.5
C8—C3—Ru1	126.41 (19)	H14B—C14—H14C	109.5
C3—C4—C5	108.1 (2)	C7—C15—H15A	109.5
C3—C4—C12	125.5 (3)	C7—C15—H15B	109.5
C5—C4—C12	126.3 (3)	H15A—C15—H15B	109.5
C3—C4—Ru1	70.06 (15)	C7—C15—H15C	109.5
C5—C4—Ru1	72.19 (16)	H15A—C15—H15C	109.5
C12—C4—Ru1	125.7 (2)	H15B—C15—H15C	109.5
C6—C5—C4	108.4 (3)

C2—Ru1—C1—O2	−85.4 (4)	Ru1ⁱ—Ru1—C5—C4	−101.12 (15)
C1ⁱ—Ru1—C1—O2	−178.9 (5)	C2—Ru1—C5—C13	−119.8 (4)
C7—Ru1—C1—O2	12.6 (5)	C1—Ru1—C5—C13	73.4 (3)
C3—Ru1—C1—O2	25.7 (4)	C1ⁱ—Ru1—C5—C13	−22.3 (3)
C6—Ru1—C1—O2	71.9 (5)	C7—Ru1—C5—C13	−156.8 (3)
C4—Ru1—C1—O2	61.3 (4)	C3—Ru1—C5—C13	159.6 (3)
C5—Ru1—C1—O2	88.0 (4)	C6—Ru1—C5—C13	−119.5 (4)
Ru1ⁱ—Ru1—C1—O2	−178.9 (5)	C4—Ru1—C5—C13	122.6 (4)
C2—Ru1—C1—Ru1ⁱ	93.50 (13)	Ru1ⁱ—Ru1—C5—C13	21.5 (3)
C1ⁱ—Ru1—C1—Ru1ⁱ	0.0	C4—C5—C6—C7	−1.5 (3)
C7—Ru1—C1—Ru1ⁱ	−168.55 (12)	C13—C5—C6—C7	−175.7 (3)
C3—Ru1—C1—Ru1ⁱ	−155.46 (10)	Ru1—C5—C6—C7	60.44 (19)
C6—Ru1—C1—Ru1ⁱ	−109.3 (2)	C4—C5—C6—C14	176.4 (3)
C4—Ru1—C1—Ru1ⁱ	−119.83 (10)	C13—C5—C6—C14	2.2 (5)
C5—Ru1—C1—Ru1ⁱ	−93.11 (11)	Ru1—C5—C6—C14	−121.6 (3)
C2—Ru1—C3—C4	174.96 (17)	C4—C5—C6—Ru1	−61.97 (18)
C1—Ru1—C3—C4	78.61 (17)	C13—C5—C6—Ru1	123.9 (3)
C1ⁱ—Ru1—C3—C4	−40.9 (3)	C2—Ru1—C6—C7	62.3 (2)
C7—Ru1—C3—C4	−116.2 (2)	C1—Ru1—C6—C7	−92.8 (3)
C6—Ru1—C3—C4	−78.47 (17)	C1ⁱ—Ru1—C6—C7	157.92 (18)
C5—Ru1—C3—C4	−36.95 (16)	C3—Ru1—C6—C7	−39.01 (17)
Ru1ⁱ—Ru1—C3—C4	49.3 (2)	C4—Ru1—C6—C7	−80.71 (18)
C2—Ru1—C3—C7	−68.8 (2)	C5—Ru1—C6—C7	−117.6 (2)
C1—Ru1—C3—C7	−165.16 (18)	Ru1ⁱ—Ru1—C6—C7	−174.32 (13)
C1ⁱ—Ru1—C3—C7	75.4 (3)	C2—Ru1—C6—C5	179.85 (18)
C6—Ru1—C3—C7	37.75 (17)	C1—Ru1—C6—C5	24.8 (3)
C4—Ru1—C3—C7	116.2 (2)	C1ⁱ—Ru1—C6—C5	−84.50 (18)
C5—Ru1—C3—C7	79.27 (18)	C7—Ru1—C6—C5	117.6 (2)
Ru1ⁱ—Ru1—C3—C7	165.55 (13)	C3—Ru1—C6—C5	78.57 (18)
C2—Ru1—C3—C8	51.7 (3)	C4—Ru1—C6—C5	36.87 (16)
C1—Ru1—C3—C8	−44.6 (3)	Ru1ⁱ—Ru1—C6—C5	−56.74 (19)
C1ⁱ—Ru1—C3—C8	−164.1 (2)	C2—Ru1—C6—C14	−58.7 (3)
C7—Ru1—C3—C8	120.5 (3)	C1—Ru1—C6—C14	146.3 (3)
C6—Ru1—C3—C8	158.3 (3)	C1ⁱ—Ru1—C6—C14	36.9 (3)
C4—Ru1—C3—C8	−123.2 (3)	C7—Ru1—C6—C14	−121.0 (4)
C5—Ru1—C3—C8	−160.2 (3)	C3—Ru1—C6—C14	−160.0 (3)
Ru1ⁱ—Ru1—C3—C8	−73.9 (3)	C4—Ru1—C6—C14	158.3 (3)
C7—C3—C4—C5	0.5 (3)	C5—Ru1—C6—C14	121.4 (4)
C8—C3—C4—C5	−174.1 (3)	Ru1ⁱ—Ru1—C6—C14	64.7 (3)
Ru1—C3—C4—C5	62.55 (18)	C5—C6—C7—C3	1.8 (3)
C7—C3—C4—C12	177.7 (3)	C14—C6—C7—C3	−176.0 (3)
C8—C3—C4—C12	3.1 (4)	Ru1—C6—C7—C3	64.53 (19)
Ru1—C3—C4—C12	−120.3 (3)	C5—C6—C7—C15	174.8 (3)
C7—C3—C4—Ru1	−62.02 (18)	C14—C6—C7—C15	−3.1 (5)
C8—C3—C4—Ru1	123.4 (3)	Ru1—C6—C7—C15	−122.6 (3)
C2—Ru1—C4—C3	−8.6 (3)	C5—C6—C7—Ru1	−62.68 (19)
C1—Ru1—C4—C3	−104.80 (17)	C14—C6—C7—Ru1	119.4 (3)
C1ⁱ—Ru1—C4—C3	159.04 (16)	C4—C3—C7—C6	−1.5 (3)
C7—Ru1—C4—C3	38.80 (16)	C8—C3—C7—C6	173.1 (3)
C6—Ru1—C4—C3	80.91 (17)	Ru1—C3—C7—C6	−65.85 (19)
C5—Ru1—C4—C3	117.6 (2)	C4—C3—C7—C15	−174.4 (3)
Ru1ⁱ—Ru1—C4—C3	−148.89 (13)	C8—C3—C7—C15	0.2 (5)
C2—Ru1—C4—C5	−126.2 (2)	Ru1—C3—C7—C15	121.2 (3)
C1—Ru1—C4—C5	137.56 (18)	C4—C3—C7—Ru1	64.38 (18)
C1ⁱ—Ru1—C4—C5	41.4 (2)	C8—C3—C7—Ru1	−121.0 (3)
C7—Ru1—C4—C5	−78.84 (18)	C2—Ru1—C7—C6	−125.6 (2)
C3—Ru1—C4—C5	−117.6 (2)	C1—Ru1—C7—C6	136.91 (19)
C6—Ru1—C4—C5	−36.73 (17)	C1ⁱ—Ru1—C7—C6	−28.5 (2)
Ru1ⁱ—Ru1—C4—C5	93.47 (16)	C3—Ru1—C7—C6	115.6 (2)
C2—Ru1—C4—C12	111.4 (3)	C4—Ru1—C7—C6	78.44 (18)
C1—Ru1—C4—C12	15.2 (3)	C5—Ru1—C7—C6	36.77 (16)
C1ⁱ—Ru1—C4—C12	−81.0 (3)	C2—Ru1—C7—C3	118.77 (19)
C7—Ru1—C4—C12	158.8 (3)	C1—Ru1—C7—C3	21.3 (3)
C3—Ru1—C4—C12	120.0 (3)	C1ⁱ—Ru1—C7—C3	−144.14 (17)
C6—Ru1—C4—C12	−159.1 (3)	C6—Ru1—C7—C3	−115.6 (2)
C5—Ru1—C4—C12	−122.4 (3)	C4—Ru1—C7—C3	−37.20 (16)
Ru1ⁱ—Ru1—C4—C12	−28.9 (3)	C5—Ru1—C7—C3	−78.87 (18)
C3—C4—C5—C6	0.6 (3)	C2—Ru1—C7—C15	−2.7 (3)
C12—C4—C5—C6	−176.5 (3)	C1—Ru1—C7—C15	−100.2 (3)
Ru1—C4—C5—C6	61.80 (18)	C1ⁱ—Ru1—C7—C15	94.4 (3)
C3—C4—C5—C13	174.6 (3)	C3—Ru1—C7—C15	−121.5 (3)
C12—C4—C5—C13	−2.5 (4)	C6—Ru1—C7—C15	122.9 (3)
Ru1—C4—C5—C13	−124.2 (3)	C4—Ru1—C7—C15	−158.7 (3)
C3—C4—C5—Ru1	−61.19 (18)	C5—Ru1—C7—C15	159.7 (3)
C12—C4—C5—Ru1	121.7 (3)	C4—C3—C8—C9	−114.8 (4)
C2—Ru1—C5—C6	−0.3 (3)	C7—C3—C8—C9	71.6 (5)
C1—Ru1—C5—C6	−167.05 (16)	Ru1—C3—C8—C9	−18.8 (5)
C1ⁱ—Ru1—C5—C6	97.23 (18)	C4—C3—C8—S1	69.0 (3)
C7—Ru1—C5—C6	−37.27 (17)	C7—C3—C8—S1	−104.6 (3)
C3—Ru1—C5—C6	−80.92 (18)	Ru1—C3—C8—S1	164.94 (16)
C4—Ru1—C5—C6	−117.9 (2)	C11—S1—C8—C9	1.7 (3)
Ru1ⁱ—Ru1—C5—C6	141.01 (15)	C11—S1—C8—C3	178.6 (3)
C2—Ru1—C5—C4	117.6 (3)	C3—C8—C9—C10	−178.1 (3)
C1—Ru1—C5—C4	−49.17 (19)	S1—C8—C9—C10	−1.6 (4)
C1ⁱ—Ru1—C5—C4	−144.90 (17)	C8—C9—C10—C11	0.6 (5)
C7—Ru1—C5—C4	80.60 (18)	C9—C10—C11—S1	0.7 (5)
C3—Ru1—C5—C4	36.96 (16)	C8—S1—C11—C10	−1.4 (4)
C6—Ru1—C5—C4	117.9 (2)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱⁱ	0.93	2.60	3.335 (5)	136
C14—H14B···O2ⁱ	0.96	2.58	3.319 (4)	134

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Ru₂(C₁₃H₁₅S)₂(CO)₄]
M_r	720.82
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	8.269 (2), 8.899 (3), 10.056 (3)
α, β, γ (°)	81.826 (4), 76.083 (5), 82.876 (5)
V (Å³)	707.9 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.25
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.835, 0.885
No. of measured, independent and observed [I > 2σ(I)] reflections	3667, 2493, 2431
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.100, 1.03
No. of reflections	2493
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.63

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ru1—C1	2.018 (3)	Ru1—C5	2.302 (3)
Ru1—C1ⁱ	2.048 (3)	Ru1—C6	2.282 (3)
Ru1—C2	1.862 (3)	Ru1—C7	2.217 (3)
Ru1—C3	2.246 (3)	Ru1—Ru1ⁱ	2.7511 (8)
Ru1—C4	2.291 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱⁱ	0.93	2.60	3.335 (5)	136
C14—H14B···O2ⁱ	0.96	2.58	3.319 (4)	134

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y, −z+1.

Acknowledgements

This work was supported financially by the Hebei Natural Science Foundation of China (No. B2008000150) and the Research Fund for the Doctoral Program of Hebei Normal University (No. L2005B18).

References

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