Experimental
Crystal data
[Ru2(C13H15S)2(CO)4] Mr = 720.82 Triclinic, ![[P \overline 1]](teximages/hy2205fi1.gif) 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
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Data collection
Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) Tmin = 0.835, Tmax = 0.885 3667 measured reflections 2493 independent reflections 2431 reflections with I > 2σ(I) Rint = 0.016
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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. | |
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
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%.
H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (CH) and 0.96 (CH3) Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C).
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).
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 |
Mr = 720.82 | F(000) = 362 |
Triclinic, P1 | Dx = 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 | Rint = 0.016 |
ϕ and ω scans | θmax = 25.1°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.835, Tmax = 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(Fo2) + (0.09P)2 + 0.0001P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2493 reflections | Δρmax = 0.53 e Å−3 |
173 parameters | Δρmin = −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)° |
Mr = 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) |
Tmin = 0.835, Tmax = 0.885 | Rint = 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 | Δρmax = 0.53 e Å−3 |
2493 reflections | Δρmin = −0.63 e Å−3 |
173 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
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] |
Mr | 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) |
Tmin, Tmax | 0.835, 0.885 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3667, 2493, 2431 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.53, −0.63 |
Selected bond lengths (Å) topRu1—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
Arndt, S. O. (2002). J. Chem. Rev. 102, 1953–1976. Web of Science CrossRef CAS Google Scholar
Bailey, N. A., Radford, S. L., Sanderson, J. A., Tabatabaian, K., White, C. & Worthington, J. A. (1978). J. Organomet. Chem. 154, 343–351. CSD CrossRef CAS Web of Science Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
King, R. B. (1976). Coord. Chem. Rev. 20, 155–169. CAS Google Scholar
Möhring, P. C. & Coville, N. J. (2006). Coord. Chem. Rev. 250, 18–35. Web of Science CrossRef Google Scholar
Schumann, H., Stenz, S., Girgsdies, F. & Mühle, S. Z. (2002). Z. Naturforsch. Teil B, 57, 1017–1026. 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
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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 RuI 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).