Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021237/cf6137sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021237/cf6137Isup2.hkl |
CCDC reference: 180521
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.033
- wR factor = 0.090
- Data-to-parameter ratio = 17.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The complex [(η6-C10H14)RuCl2(DMSO)] was prepared in a 68% yield by reaction of [{(η6-C10H14)RuCl2}2] (0.612 g, 1 mmol) in dichloromethane (25 ml) with 4-cyanophenyl imidazole (0.338 g, 2 mmol) which was previously isolated from dimethylsulfoxide and therefore contained DMSO as solvate. Orange-red crystals suitable for single-crystal analysis were obtained by slow diffusion of petroleum ether (b.p. 333–353 K) into a solution of the complex in dichloromethane.
The highest residual peak lies 0.919 Å from Ru1. All H atoms were placed in calculated positions and refined with a riding model.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The structure of [(η6-C10H14)RuCl2(DMSO)] showing 50% probability displacement ellipsoids. |
[RuCl2(C10H14)(C2H6OS)] | Z = 2 |
Mr = 384.31 | F(000) = 388 |
Triclinic, P1 | Dx = 1.692 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8522 (16) Å | Cell parameters from 25 reflections |
b = 9.4124 (9) Å | θ = 5.2–12.1° |
c = 10.9151 (17) Å | µ = 1.51 mm−1 |
α = 106.850 (11)° | T = 293 K |
β = 94.395 (15)° | Needle, brown |
γ = 99.697 (13)° | 0.4 × 0.1 × 0.1 mm |
V = 754.3 (2) Å3 |
Enraf-Nonius CAD-4 diffractometer | 2373 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω/2θ scans | h = −9→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→11 |
Tmin = 0.836, Tmax = 0.860 | l = −12→12 |
2632 measured reflections | 3 standard reflections every 100 reflections |
2632 independent reflections | intensity decay: none |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.067P)2] where P = (Fo2 + 2Fc2)/3 |
2632 reflections | (Δ/σ)max = 0.001 |
154 parameters | Δρmax = 1.26 e Å−3 |
0 restraints | Δρmin = −0.83 e Å−3 |
[RuCl2(C10H14)(C2H6OS)] | γ = 99.697 (13)° |
Mr = 384.31 | V = 754.3 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.8522 (16) Å | Mo Kα radiation |
b = 9.4124 (9) Å | µ = 1.51 mm−1 |
c = 10.9151 (17) Å | T = 293 K |
α = 106.850 (11)° | 0.4 × 0.1 × 0.1 mm |
β = 94.395 (15)° |
Enraf-Nonius CAD-4 diffractometer | 2373 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.000 |
Tmin = 0.836, Tmax = 0.860 | 3 standard reflections every 100 reflections |
2632 measured reflections | intensity decay: none |
2632 independent reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.07 | Δρmax = 1.26 e Å−3 |
2632 reflections | Δρmin = −0.83 e Å−3 |
154 parameters |
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. ' |
x | y | z | Uiso*/Ueq | ||
Ru1 | 0.29833 (3) | 0.31308 (3) | 0.26131 (2) | 0.02468 (13) | |
Cl1 | 0.58313 (11) | 0.25448 (12) | 0.29023 (9) | 0.0407 (2) | |
Cl2 | 0.43520 (14) | 0.53239 (11) | 0.20865 (10) | 0.0467 (3) | |
S1 | 0.28705 (12) | 0.17812 (10) | 0.04298 (8) | 0.0327 (2) | |
C1 | 0.2167 (4) | 0.1968 (4) | 0.4017 (3) | 0.0298 (7) | |
C2 | 0.2655 (5) | 0.3569 (4) | 0.4671 (3) | 0.0341 (8) | |
H2 | 0.3477 | 0.3923 | 0.5407 | 0.041* | |
C3 | 0.1921 (5) | 0.4590 (4) | 0.4222 (4) | 0.0368 (9) | |
H3 | 0.2254 | 0.5620 | 0.4664 | 0.044* | |
C4 | 0.0655 (5) | 0.4093 (4) | 0.3088 (4) | 0.0342 (8) | |
C5 | 0.0137 (4) | 0.2525 (4) | 0.2463 (3) | 0.0325 (8) | |
H5 | −0.0709 | 0.2173 | 0.1742 | 0.039* | |
C6 | 0.0890 (4) | 0.1479 (4) | 0.2919 (3) | 0.0291 (7) | |
H6 | 0.0537 | 0.0448 | 0.2487 | 0.035* | |
C7 | 0.3045 (5) | 0.0871 (5) | 0.4507 (4) | 0.0390 (9) | |
H7 | 0.4303 | 0.1270 | 0.4640 | 0.047* | |
C8 | 0.2726 (7) | −0.0713 (5) | 0.3530 (5) | 0.0570 (12) | |
H8A | 0.3275 | −0.1363 | 0.3895 | 0.086* | |
H8B | 0.3208 | −0.0658 | 0.2760 | 0.086* | |
H8C | 0.1495 | −0.1114 | 0.3324 | 0.086* | |
C9 | 0.2518 (6) | 0.0862 (6) | 0.5823 (4) | 0.0556 (12) | |
H9A | 0.3077 | 0.0172 | 0.6126 | 0.083* | |
H9B | 0.1276 | 0.0545 | 0.5744 | 0.083* | |
H9C | 0.2870 | 0.1862 | 0.6426 | 0.083* | |
C10 | −0.0103 (6) | 0.5216 (5) | 0.2576 (5) | 0.0537 (11) | |
H10A | 0.0354 | 0.6224 | 0.3142 | 0.081* | |
H10B | −0.1349 | 0.4999 | 0.2533 | 0.081* | |
H10C | 0.0207 | 0.5138 | 0.1729 | 0.081* | |
O1 | 0.2148 (4) | 0.0139 (3) | 0.0064 (3) | 0.0498 (7) | |
C11 | 0.4867 (6) | 0.2036 (5) | −0.0214 (4) | 0.0475 (10) | |
H11A | 0.5346 | 0.3098 | −0.0003 | 0.071* | |
H11B | 0.4661 | 0.1590 | −0.1136 | 0.071* | |
H11C | 0.5673 | 0.1556 | 0.0147 | 0.071* | |
C12 | 0.1588 (6) | 0.2555 (6) | −0.0535 (4) | 0.0564 (12) | |
H12A | 0.2038 | 0.3622 | −0.0329 | 0.085* | |
H12B | 0.0402 | 0.2393 | −0.0363 | 0.085* | |
H12C | 0.1634 | 0.2066 | −0.1432 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.02448 (18) | 0.02340 (18) | 0.01861 (18) | −0.00334 (11) | −0.00319 (11) | 0.00100 (12) |
Cl1 | 0.0266 (4) | 0.0573 (6) | 0.0353 (5) | 0.0044 (4) | 0.0000 (4) | 0.0131 (5) |
Cl2 | 0.0561 (6) | 0.0332 (5) | 0.0460 (6) | −0.0071 (4) | 0.0063 (5) | 0.0140 (4) |
S1 | 0.0337 (5) | 0.0355 (5) | 0.0206 (4) | 0.0021 (4) | −0.0016 (4) | 0.0001 (4) |
C1 | 0.0292 (18) | 0.0345 (19) | 0.0241 (17) | 0.0005 (14) | 0.0040 (14) | 0.0099 (15) |
C2 | 0.0320 (19) | 0.040 (2) | 0.0221 (17) | −0.0026 (16) | 0.0016 (14) | 0.0021 (15) |
C3 | 0.040 (2) | 0.0271 (18) | 0.033 (2) | 0.0013 (15) | 0.0098 (16) | −0.0042 (16) |
C4 | 0.0313 (19) | 0.0343 (19) | 0.037 (2) | 0.0098 (15) | 0.0084 (16) | 0.0078 (16) |
C5 | 0.0225 (17) | 0.039 (2) | 0.0307 (18) | −0.0027 (15) | −0.0007 (14) | 0.0087 (16) |
C6 | 0.0232 (16) | 0.0282 (17) | 0.0284 (18) | −0.0071 (13) | 0.0016 (14) | 0.0043 (15) |
C7 | 0.0291 (19) | 0.051 (2) | 0.040 (2) | 0.0027 (17) | 0.0011 (16) | 0.0233 (19) |
C8 | 0.061 (3) | 0.045 (3) | 0.065 (3) | 0.013 (2) | −0.004 (2) | 0.019 (2) |
C9 | 0.049 (3) | 0.080 (3) | 0.050 (3) | 0.004 (2) | 0.005 (2) | 0.043 (3) |
C10 | 0.054 (3) | 0.044 (2) | 0.070 (3) | 0.020 (2) | 0.013 (2) | 0.021 (2) |
O1 | 0.0529 (18) | 0.0351 (15) | 0.0428 (17) | −0.0036 (13) | 0.0033 (14) | −0.0088 (13) |
C11 | 0.047 (2) | 0.062 (3) | 0.033 (2) | 0.008 (2) | 0.0143 (18) | 0.014 (2) |
C12 | 0.062 (3) | 0.078 (3) | 0.027 (2) | 0.020 (3) | −0.008 (2) | 0.013 (2) |
Ru1—Cl1 | 2.4111 (10) | C5—C6 | 1.416 (5) |
Ru1—Cl2 | 2.4045 (10) | C5—H5 | 0.930 |
Ru1—S1 | 2.3400 (10) | C6—H6 | 0.930 |
Ru1—C1 | 2.201 (3) | C7—C9 | 1.527 (5) |
Ru1—C2 | 2.207 (4) | C7—C8 | 1.527 (6) |
Ru1—C3 | 2.209 (3) | C7—H7 | 0.980 |
Ru1—C4 | 2.205 (4) | C8—H8A | 0.960 |
Ru1—C5 | 2.192 (3) | C8—H8B | 0.960 |
Ru1—C6 | 2.181 (3) | C8—H8C | 0.960 |
S1—O1 | 1.477 (3) | C9—H9A | 0.960 |
S1—C11 | 1.774 (4) | C9—H9B | 0.960 |
S1—C12 | 1.784 (4) | C9—H9C | 0.960 |
C1—C6 | 1.412 (5) | C10—H10A | 0.960 |
C1—C2 | 1.438 (5) | C10—H10B | 0.960 |
C1—C7 | 1.527 (5) | C10—H10C | 0.960 |
C2—C3 | 1.383 (6) | C11—H11A | 0.960 |
C2—H2 | 0.930 | C11—H11B | 0.960 |
C3—C4 | 1.435 (6) | C11—H11C | 0.960 |
C3—H3 | 0.930 | C12—H12A | 0.960 |
C4—C5 | 1.407 (5) | C12—H12B | 0.960 |
C4—C10 | 1.512 (6) | C12—H12C | 0.960 |
Cl1—Ru1—Cl2 | 88.05 (4) | C2—C3—H3 | 119.3 |
S1—Ru1—Cl1 | 86.28 (4) | C4—C3—H3 | 119.3 |
S1—Ru1—Cl2 | 86.74 (4) | Ru1—C3—H3 | 130.9 |
O1—S1—Ru1 | 115.71 (13) | C5—C4—C3 | 118.0 (3) |
C11—S1—Ru1 | 115.07 (15) | C5—C4—C10 | 120.9 (4) |
C12—S1—Ru1 | 109.49 (16) | C3—C4—C10 | 121.2 (4) |
O1—S1—C11 | 108.2 (2) | C5—C4—Ru1 | 70.8 (2) |
O1—S1—C12 | 107.5 (2) | C3—C4—Ru1 | 71.2 (2) |
C11—S1—C12 | 99.5 (2) | C10—C4—Ru1 | 129.2 (3) |
C6—Ru1—C5 | 37.77 (13) | C4—C5—C6 | 120.7 (3) |
C6—Ru1—C1 | 37.60 (13) | C4—C5—Ru1 | 71.8 (2) |
C5—Ru1—C1 | 68.26 (13) | C6—C5—Ru1 | 70.67 (19) |
C6—Ru1—C4 | 68.02 (14) | C4—C5—H5 | 119.6 |
C5—Ru1—C4 | 37.31 (14) | C6—C5—H5 | 119.6 |
C1—Ru1—C4 | 81.25 (14) | Ru1—C5—H5 | 130.5 |
C6—Ru1—C2 | 67.51 (13) | C1—C6—C5 | 121.3 (3) |
C5—Ru1—C2 | 79.59 (14) | C1—C6—Ru1 | 71.98 (19) |
C1—Ru1—C2 | 38.07 (13) | C5—C6—Ru1 | 71.56 (19) |
C4—Ru1—C2 | 67.69 (14) | C1—C6—H6 | 119.3 |
C6—Ru1—C3 | 79.41 (14) | C5—C6—H6 | 119.3 |
C5—Ru1—C3 | 67.19 (14) | Ru1—C6—H6 | 129.7 |
C1—Ru1—C3 | 67.64 (14) | C1—C7—C9 | 109.9 (3) |
C4—Ru1—C3 | 37.94 (15) | C1—C7—C8 | 112.9 (3) |
C2—Ru1—C3 | 36.52 (15) | C9—C7—C8 | 112.9 (4) |
C6—Ru1—S1 | 93.36 (10) | C1—C7—H7 | 106.9 |
C5—Ru1—S1 | 90.42 (10) | C9—C7—H7 | 106.9 |
C1—Ru1—S1 | 121.06 (10) | C8—C7—H7 | 106.9 |
C4—Ru1—S1 | 114.19 (11) | C7—C8—H8A | 109.5 |
C2—Ru1—S1 | 159.07 (10) | C7—C8—H8B | 109.5 |
C3—Ru1—S1 | 151.89 (11) | H8A—C8—H8B | 109.5 |
C6—Ru1—Cl2 | 158.37 (10) | C7—C8—H8C | 109.5 |
C5—Ru1—Cl2 | 120.62 (10) | H8A—C8—H8C | 109.5 |
C1—Ru1—Cl2 | 151.75 (10) | H8B—C8—H8C | 109.5 |
C4—Ru1—Cl2 | 92.21 (10) | C7—C9—H9A | 109.5 |
C2—Ru1—Cl2 | 114.18 (10) | C7—C9—H9B | 109.5 |
C3—Ru1—Cl2 | 90.35 (10) | H9A—C9—H9B | 109.5 |
C6—Ru1—Cl1 | 113.55 (10) | C7—C9—H9C | 109.5 |
C5—Ru1—Cl1 | 150.93 (10) | H9A—C9—H9C | 109.5 |
C1—Ru1—Cl1 | 88.87 (10) | H9B—C9—H9C | 109.5 |
C4—Ru1—Cl1 | 159.51 (11) | C4—C10—H10A | 109.5 |
C2—Ru1—Cl1 | 93.56 (10) | C4—C10—H10B | 109.5 |
C3—Ru1—Cl1 | 121.59 (11) | H10A—C10—H10B | 109.5 |
C6—C1—C2 | 117.6 (3) | C4—C10—H10C | 109.5 |
C6—C1—C7 | 122.5 (3) | H10A—C10—H10C | 109.5 |
C2—C1—C7 | 119.8 (3) | H10B—C10—H10C | 109.5 |
C6—C1—Ru1 | 70.42 (19) | S1—C11—H11A | 109.5 |
C2—C1—Ru1 | 71.2 (2) | S1—C11—H11B | 109.5 |
C7—C1—Ru1 | 128.6 (2) | H11A—C11—H11B | 109.5 |
C3—C2—C1 | 120.9 (3) | S1—C11—H11C | 109.5 |
C3—C2—Ru1 | 71.8 (2) | H11A—C11—H11C | 109.5 |
C1—C2—Ru1 | 70.7 (2) | H11B—C11—H11C | 109.5 |
C3—C2—H2 | 119.5 | S1—C12—H12A | 109.5 |
C1—C2—H2 | 119.5 | S1—C12—H12B | 109.5 |
Ru1—C2—H2 | 130.6 | H12A—C12—H12B | 109.5 |
C2—C3—C4 | 121.4 (3) | S1—C12—H12C | 109.5 |
C2—C3—Ru1 | 71.7 (2) | H12A—C12—H12C | 109.5 |
C4—C3—Ru1 | 70.9 (2) | H12B—C12—H12C | 109.5 |
C6—Ru1—S1—O1 | −24.25 (17) | C2—Ru1—C3—C4 | −134.0 (3) |
C5—Ru1—S1—O1 | −61.93 (18) | S1—Ru1—C3—C4 | 9.4 (4) |
C1—Ru1—S1—O1 | 2.73 (18) | Cl2—Ru1—C3—C4 | 93.1 (2) |
C4—Ru1—S1—O1 | −91.63 (18) | Cl1—Ru1—C3—C4 | −178.94 (18) |
C2—Ru1—S1—O1 | −1.1 (3) | C2—C3—C4—C5 | 1.9 (5) |
C3—Ru1—S1—O1 | −97.9 (3) | Ru1—C3—C4—C5 | 55.0 (3) |
Cl2—Ru1—S1—O1 | 177.41 (15) | C2—C3—C4—C10 | −178.1 (4) |
Cl1—Ru1—S1—O1 | 89.16 (15) | Ru1—C3—C4—C10 | −125.0 (4) |
C6—Ru1—S1—C11 | −151.7 (2) | C2—C3—C4—Ru1 | −53.1 (3) |
C5—Ru1—S1—C11 | 170.7 (2) | C6—Ru1—C4—C5 | −28.8 (2) |
C1—Ru1—S1—C11 | −124.7 (2) | C1—Ru1—C4—C5 | −65.4 (2) |
C4—Ru1—S1—C11 | 141.0 (2) | C2—Ru1—C4—C5 | −102.5 (2) |
C2—Ru1—S1—C11 | −128.5 (3) | C3—Ru1—C4—C5 | −130.0 (3) |
C3—Ru1—S1—C11 | 134.7 (3) | S1—Ru1—C4—C5 | 54.8 (2) |
Cl2—Ru1—S1—C11 | 50.01 (18) | Cl2—Ru1—C4—C5 | 142.2 (2) |
Cl1—Ru1—S1—C11 | −38.24 (18) | Cl1—Ru1—C4—C5 | −127.4 (3) |
C6—Ru1—S1—C12 | 97.3 (2) | C6—Ru1—C4—C3 | 101.3 (2) |
C5—Ru1—S1—C12 | 59.6 (2) | C5—Ru1—C4—C3 | 130.0 (3) |
C1—Ru1—S1—C12 | 124.3 (2) | C1—Ru1—C4—C3 | 64.6 (2) |
C4—Ru1—S1—C12 | 30.0 (2) | C2—Ru1—C4—C3 | 27.5 (2) |
C2—Ru1—S1—C12 | 120.5 (3) | S1—Ru1—C4—C3 | −175.16 (19) |
C3—Ru1—S1—C12 | 23.6 (3) | Cl2—Ru1—C4—C3 | −87.7 (2) |
Cl2—Ru1—S1—C12 | −61.01 (19) | Cl1—Ru1—C4—C3 | 2.6 (4) |
Cl1—Ru1—S1—C12 | −149.26 (19) | C6—Ru1—C4—C10 | −143.4 (4) |
C5—Ru1—C1—C6 | 28.7 (2) | C5—Ru1—C4—C10 | −114.7 (5) |
C4—Ru1—C1—C6 | 65.1 (2) | C1—Ru1—C4—C10 | 179.9 (4) |
C2—Ru1—C1—C6 | 129.9 (3) | C2—Ru1—C4—C10 | 142.8 (4) |
C3—Ru1—C1—C6 | 102.0 (2) | C3—Ru1—C4—C10 | 115.3 (5) |
S1—Ru1—C1—C6 | −47.9 (2) | S1—Ru1—C4—C10 | −59.9 (4) |
Cl2—Ru1—C1—C6 | 143.3 (2) | Cl2—Ru1—C4—C10 | 27.5 (4) |
Cl1—Ru1—C1—C6 | −132.9 (2) | Cl1—Ru1—C4—C10 | 117.9 (4) |
C6—Ru1—C1—C2 | −129.9 (3) | C3—C4—C5—C6 | −2.0 (5) |
C5—Ru1—C1—C2 | −101.2 (2) | C10—C4—C5—C6 | 177.9 (4) |
C4—Ru1—C1—C2 | −64.8 (2) | Ru1—C4—C5—C6 | 53.1 (3) |
C3—Ru1—C1—C2 | −27.8 (2) | C3—C4—C5—Ru1 | −55.1 (3) |
S1—Ru1—C1—C2 | −177.80 (17) | C10—C4—C5—Ru1 | 124.8 (4) |
Cl2—Ru1—C1—C2 | 13.5 (3) | C6—Ru1—C5—C4 | 133.3 (3) |
Cl1—Ru1—C1—C2 | 97.2 (2) | C1—Ru1—C5—C4 | 104.7 (2) |
C6—Ru1—C1—C7 | 116.5 (4) | C2—Ru1—C5—C4 | 66.7 (2) |
C5—Ru1—C1—C7 | 145.2 (4) | C3—Ru1—C5—C4 | 30.7 (2) |
C4—Ru1—C1—C7 | −178.4 (3) | S1—Ru1—C5—C4 | −131.8 (2) |
C2—Ru1—C1—C7 | −113.6 (4) | Cl2—Ru1—C5—C4 | −45.3 (2) |
C3—Ru1—C1—C7 | −141.4 (4) | Cl1—Ru1—C5—C4 | 145.1 (2) |
S1—Ru1—C1—C7 | 68.6 (3) | C1—Ru1—C5—C6 | −28.6 (2) |
Cl2—Ru1—C1—C7 | −100.1 (3) | C4—Ru1—C5—C6 | −133.3 (3) |
Cl1—Ru1—C1—C7 | −16.4 (3) | C2—Ru1—C5—C6 | −66.6 (2) |
C6—C1—C2—C3 | −1.2 (5) | C3—Ru1—C5—C6 | −102.5 (2) |
C7—C1—C2—C3 | 177.8 (3) | S1—Ru1—C5—C6 | 94.9 (2) |
Ru1—C1—C2—C3 | 53.5 (3) | Cl2—Ru1—C5—C6 | −178.59 (16) |
C6—C1—C2—Ru1 | −54.7 (3) | Cl1—Ru1—C5—C6 | 11.9 (3) |
C7—C1—C2—Ru1 | 124.4 (3) | C2—C1—C6—C5 | 1.1 (5) |
C6—Ru1—C2—C3 | −103.0 (2) | C7—C1—C6—C5 | −178.0 (3) |
C5—Ru1—C2—C3 | −65.5 (2) | Ru1—C1—C6—C5 | −54.0 (3) |
C1—Ru1—C2—C3 | −133.4 (3) | C2—C1—C6—Ru1 | 55.1 (3) |
C4—Ru1—C2—C3 | −28.5 (2) | C7—C1—C6—Ru1 | −123.9 (3) |
S1—Ru1—C2—C3 | −128.2 (3) | C4—C5—C6—C1 | 0.6 (5) |
Cl2—Ru1—C2—C3 | 53.5 (2) | Ru1—C5—C6—C1 | 54.2 (3) |
Cl1—Ru1—C2—C3 | 142.9 (2) | C4—C5—C6—Ru1 | −53.6 (3) |
C6—Ru1—C2—C1 | 30.4 (2) | C5—Ru1—C6—C1 | −133.2 (3) |
C5—Ru1—C2—C1 | 67.9 (2) | C4—Ru1—C6—C1 | −104.8 (2) |
C4—Ru1—C2—C1 | 104.9 (2) | C2—Ru1—C6—C1 | −30.8 (2) |
C3—Ru1—C2—C1 | 133.4 (3) | C3—Ru1—C6—C1 | −67.0 (2) |
S1—Ru1—C2—C1 | 5.3 (4) | S1—Ru1—C6—C1 | 140.4 (2) |
Cl2—Ru1—C2—C1 | −173.06 (17) | Cl2—Ru1—C6—C1 | −129.9 (2) |
Cl1—Ru1—C2—C1 | −83.6 (2) | Cl1—Ru1—C6—C1 | 53.0 (2) |
C1—C2—C3—C4 | −0.3 (6) | C1—Ru1—C6—C5 | 133.2 (3) |
Ru1—C2—C3—C4 | 52.7 (3) | C4—Ru1—C6—C5 | 28.4 (2) |
C1—C2—C3—Ru1 | −53.0 (3) | C2—Ru1—C6—C5 | 102.4 (2) |
C6—Ru1—C3—C2 | 66.3 (2) | C3—Ru1—C6—C5 | 66.3 (2) |
C5—Ru1—C3—C2 | 103.8 (2) | S1—Ru1—C6—C5 | −86.3 (2) |
C1—Ru1—C3—C2 | 29.0 (2) | Cl2—Ru1—C6—C5 | 3.3 (4) |
C4—Ru1—C3—C2 | 134.0 (3) | Cl1—Ru1—C6—C5 | −173.74 (18) |
S1—Ru1—C3—C2 | 143.4 (2) | C6—C1—C7—C9 | −113.5 (4) |
Cl2—Ru1—C3—C2 | −132.8 (2) | C2—C1—C7—C9 | 67.5 (4) |
Cl1—Ru1—C3—C2 | −44.9 (2) | Ru1—C1—C7—C9 | 156.5 (3) |
C6—Ru1—C3—C4 | −67.7 (2) | C6—C1—C7—C8 | 13.5 (5) |
C5—Ru1—C3—C4 | −30.2 (2) | C2—C1—C7—C8 | −165.6 (4) |
C1—Ru1—C3—C4 | −105.1 (2) | Ru1—C1—C7—C8 | −76.6 (4) |
Experimental details
Crystal data | |
Chemical formula | [RuCl2(C10H14)(C2H6OS)] |
Mr | 384.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.8522 (16), 9.4124 (9), 10.9151 (17) |
α, β, γ (°) | 106.850 (11), 94.395 (15), 99.697 (13) |
V (Å3) | 754.3 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.51 |
Crystal size (mm) | 0.4 × 0.1 × 0.1 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.836, 0.860 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2632, 2632, 2373 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.594 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.090, 1.07 |
No. of reflections | 2632 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.26, −0.83 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, maXus (Mackay et al., 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.
Ru1—Cl1 | 2.4111 (10) | Ru1—C4 | 2.205 (4) |
Ru1—Cl2 | 2.4045 (10) | Ru1—C5 | 2.192 (3) |
Ru1—S1 | 2.3400 (10) | Ru1—C6 | 2.181 (3) |
Ru1—C1 | 2.201 (3) | S1—O1 | 1.477 (3) |
Ru1—C2 | 2.207 (4) | S1—C11 | 1.774 (4) |
Ru1—C3 | 2.209 (3) | S1—C12 | 1.784 (4) |
Cl1—Ru1—Cl2 | 88.05 (4) | C12—S1—Ru1 | 109.49 (16) |
S1—Ru1—Cl1 | 86.28 (4) | O1—S1—C11 | 108.2 (2) |
S1—Ru1—Cl2 | 86.74 (4) | O1—S1—C12 | 107.5 (2) |
O1—S1—Ru1 | 115.71 (13) | C11—S1—C12 | 99.5 (2) |
C11—S1—Ru1 | 115.07 (15) |
The homochiral sulfoxides have received considerable attention recently owing to their prominent role as intermediates in enantioselective synthesis and their potential use as precursors (Schenk et al., 1997; Otto et al., 2001). Because of our continuing interest in the area of arene ruthenium chemistry (Singh et al., 2000), we reacted [{(η6-C10H14)RuCl2}2] with 4-cyanophenyl imidazole, which contained dimethylsulfoxide as solvate. Surprisingly, we isolated the title complex, [(η6-C10H14)RuCl2(DMSO)], (I), instead of the expected arene–ruthenium–organonitrile complex. The pertinent bond lengths and bond angles may be compared with the closely related 1,4,9,10-tetrahydroanthracene ruthenium complex [(η6-C14H14)RuCl2(DMSO)] (Beasley et al., 1993). The title compound adopts a typical piano-stool geometry (a description commonly used for half-sandwich compounds) with a pseudo-tetrahedral arrangement of the p-cymene, the two chloride ligands, and the S atom of the coordinated DMSO ligand around the ruthenium metal centre. This is a similar arrangement to that of [(η6-C10H14)RuCl2(MePPh2)], [(η6-C10H14)RuCl2(pz)2]PF6 and the η6-arene DMSO complex [(η6-C14H14)RuCl2(DMSO)] (Bennet et al., 1972; Tocher et al., 1983; Beasley et al., 1993). The six-membered ring of the p-cymene is planar, with a maximum deviation of 0.013 (3) Å (C4) and an overall r.m.s. deviation of 0.008 Å. The C—C bond lengths within the p-cymene ring are similar apart from a shortening of the C2—C3 bond. The Ru—C distances are almost equal, with an average of 2.199 (11) Å. The distance between the centroid of the p-cymene ring and ruthenium is 1.683 (3) Å, which is very close to that reported in other RuII arene complexes (Watkins & Fronczek, 1982; McCormick et al., 1993; Gupta et al., 1998). The Ru—Cl1 and Ru—Cl2 bond lengths are similar to those in other RuII complexes (Bruce et al., 1981). The DMSO ligand is bonded to ruthenium via the S atom, resulting in a roughly tetrahedral arrangement around sulfur. The Ru—S distance is comparable to those observed in the η6-arene dimethyl sulfoxide complex [(η6-C14H14)RuCl2(DMSO)] (Beasley et al., 1993) and the RuII complex [RuCl2(DMSO)4] (Mercer & Trotter, 1973).