Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802013399/om6100sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802013399/om6100Isup2.hkl |
CCDC reference: 197448
Key indicators
- Single-crystal X-ray study
- T = 128 K
- Mean (C-C) = 0.006 Å
- R factor = 0.038
- wR factor = 0.089
- Data-to-parameter ratio = 14.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5875
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
The title compound was synthesized from RuCp*(P(iPr)3)(OSO2CF3) stirred under an atmosphere of CO. Crystals were grown by diffusion of pentane into a deuterobenzene solution.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1995); molecular graphics: TEXSAN (Molecular Structure Corporation, 1992); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of the title compound shown with 50% probability displacement ellipsoids. |
[Ru(CF3O3S)(C10H15)(C9H21P)(CO)] | F(000) = 1184 |
Mr = 573.60 | Dx = 1.547 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.056 (1) Å | Cell parameters from 4749 reflections |
b = 9.1258 (5) Å | θ = 1.7–24.7° |
c = 17.005 (1) Å | µ = 0.83 mm−1 |
β = 98.796 (1)° | T = 128 K |
V = 2462.3 (3) Å3 | Tablet, orange |
Z = 4 | 0.27 × 0.13 × 0.08 mm |
SMART CCD diffractometer | 4036 independent reflections |
Radiation source: fine-focus sealed tube | 3238 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scans | θmax = 24.7°, θmin = 2.4° |
Absorption correction: empirical (using intensity measurements) (Blessing, 1995) | h = −6→18 |
Tmin = 0.81, Tmax = 0.91 | k = −10→10 |
10547 measured reflections | l = −19→19 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.05 | |
4035 reflections | (Δ/σ)max = −0.042 |
280 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.71 e Å−3 |
[Ru(CF3O3S)(C10H15)(C9H21P)(CO)] | V = 2462.3 (3) Å3 |
Mr = 573.60 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 16.056 (1) Å | µ = 0.83 mm−1 |
b = 9.1258 (5) Å | T = 128 K |
c = 17.005 (1) Å | 0.27 × 0.13 × 0.08 mm |
β = 98.796 (1)° |
SMART CCD diffractometer | 4036 independent reflections |
Absorption correction: empirical (using intensity measurements) (Blessing, 1995) | 3238 reflections with I > 2σ(I) |
Tmin = 0.81, Tmax = 0.91 | Rint = 0.047 |
10547 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.70 e Å−3 |
4035 reflections | Δρmin = −0.71 e Å−3 |
280 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 on F2 for ALL reflections except for 1 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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 | 0.80665 (2) | 0.14945 (3) | 0.35101 (2) | 0.01478 (12) | |
S1 | 0.75355 (6) | −0.03166 (11) | 0.18512 (6) | 0.0195 (2) | |
P1 | 0.66998 (6) | 0.23037 (11) | 0.37238 (6) | 0.0153 (2) | |
F1 | 0.7381 (2) | −0.3146 (3) | 0.2030 (2) | 0.0488 (8) | |
F2 | 0.6913 (2) | −0.2357 (3) | 0.08565 (15) | 0.0418 (7) | |
F3 | 0.6200 (2) | −0.2004 (3) | 0.1809 (2) | 0.0447 (7) | |
O1 | 0.8313 (2) | 0.3853 (3) | 0.2333 (2) | 0.0355 (8) | |
O2 | 0.7418 (2) | −0.0146 (3) | 0.26915 (15) | 0.0187 (6) | |
O3 | 0.7069 (2) | 0.0721 (3) | 0.1325 (2) | 0.0276 (7) | |
O4 | 0.8379 (2) | −0.0609 (3) | 0.1728 (2) | 0.0309 (7) | |
C1 | 0.8128 (3) | 0.2949 (5) | 0.2753 (2) | 0.0227 (9) | |
C2 | 0.6732 (3) | 0.3967 (4) | 0.4354 (2) | 0.0224 (10) | |
H2 | 0.7011 (3) | 0.3654 (4) | 0.4894 (2) | 0.027* | |
C3 | 0.5857 (3) | 0.4568 (5) | 0.4474 (3) | 0.0315 (11) | |
H3A | 0.5512 (3) | 0.3765 (5) | 0.4630 (3) | 0.038* | |
H3B | 0.5578 (3) | 0.5003 (5) | 0.3976 (3) | 0.038* | |
H3C | 0.5930 (3) | 0.5316 (5) | 0.4893 (3) | 0.038* | |
C4 | 0.7275 (3) | 0.5198 (5) | 0.4112 (3) | 0.0328 (11) | |
H4A | 0.7826 (3) | 0.4807 (5) | 0.4037 (3) | 0.039* | |
H4B | 0.7352 (3) | 0.5947 (5) | 0.4530 (3) | 0.039* | |
H4C | 0.6999 (3) | 0.5635 (5) | 0.3613 (3) | 0.039* | |
C5 | 0.5909 (2) | 0.2789 (4) | 0.2842 (2) | 0.0192 (9) | |
H5 | 0.5470 (2) | 0.3387 (4) | 0.3053 (2) | 0.023* | |
C6 | 0.6269 (3) | 0.3780 (5) | 0.2245 (2) | 0.0251 (10) | |
H6A | 0.6572 (3) | 0.4602 (5) | 0.2528 (2) | 0.030* | |
H6B | 0.5807 (3) | 0.4157 (5) | 0.1853 (2) | 0.030* | |
H6C | 0.6657 (3) | 0.3214 (5) | 0.1971 (2) | 0.030* | |
C7 | 0.5437 (3) | 0.1512 (5) | 0.2393 (2) | 0.0261 (10) | |
H7A | 0.5204 (3) | 0.0877 (5) | 0.2770 (2) | 0.031* | |
H7B | 0.5826 (3) | 0.0948 (5) | 0.2120 (2) | 0.031* | |
H7C | 0.4977 (3) | 0.1894 (5) | 0.2001 (2) | 0.031* | |
C8 | 0.6072 (3) | 0.0981 (5) | 0.4242 (2) | 0.0240 (10) | |
H8 | 0.5464 (3) | 0.1243 (5) | 0.4084 (2) | 0.029* | |
C9 | 0.6256 (3) | 0.1052 (5) | 0.5148 (3) | 0.0320 (11) | |
H9A | 0.6186 (3) | 0.2062 (5) | 0.5323 (3) | 0.038* | |
H9B | 0.6835 (3) | 0.0730 (5) | 0.5329 (3) | 0.038* | |
H9C | 0.5863 (3) | 0.0411 (5) | 0.5373 (3) | 0.038* | |
C10 | 0.6178 (3) | −0.0594 (5) | 0.3964 (3) | 0.0277 (10) | |
H10A | 0.6059 (3) | −0.0634 (5) | 0.3382 (3) | 0.033* | |
H10B | 0.5785 (3) | −0.1236 (5) | 0.4189 (3) | 0.033* | |
H10C | 0.6757 (3) | −0.0919 (5) | 0.4144 (3) | 0.033* | |
C11 | 0.6981 (3) | −0.2056 (5) | 0.1631 (2) | 0.0266 (10) | |
C12 | 0.8806 (2) | 0.1778 (5) | 0.4713 (2) | 0.0222 (10) | |
C13 | 0.9300 (3) | 0.2246 (5) | 0.4117 (2) | 0.0226 (9) | |
C14 | 0.9438 (3) | 0.0991 (5) | 0.3642 (2) | 0.0242 (10) | |
C15 | 0.9039 (3) | −0.0229 (5) | 0.3950 (2) | 0.0238 (10) | |
C16 | 0.8661 (2) | 0.0229 (5) | 0.4613 (2) | 0.0206 (9) | |
C17 | 0.8645 (3) | 0.2671 (5) | 0.5420 (2) | 0.0273 (10) | |
H17A | 0.8794 (3) | 0.3696 (5) | 0.5342 (2) | 0.033* | |
H17B | 0.8988 (3) | 0.2290 (5) | 0.5903 (2) | 0.033* | |
H17C | 0.8047 (3) | 0.2607 (5) | 0.5474 (2) | 0.033* | |
C18 | 0.9692 (3) | 0.3730 (5) | 0.4074 (3) | 0.0323 (11) | |
H18A | 0.9490 (3) | 0.4384 (5) | 0.4462 (3) | 0.039* | |
H18B | 0.9534 (3) | 0.4133 (5) | 0.3538 (3) | 0.039* | |
H18C | 1.0306 (3) | 0.3643 (5) | 0.4195 (3) | 0.039* | |
C19 | 0.9969 (3) | 0.0968 (6) | 0.2980 (3) | 0.0377 (12) | |
H19A | 1.0164 (3) | 0.1962 (6) | 0.2889 (3) | 0.045* | |
H19B | 0.9630 (3) | 0.0600 (6) | 0.2491 (3) | 0.045* | |
H19C | 1.0456 (3) | 0.0325 (6) | 0.3130 (3) | 0.045* | |
C20 | 0.9009 (3) | −0.1770 (5) | 0.3636 (3) | 0.0335 (11) | |
H20A | 0.8694 (3) | −0.2390 (5) | 0.3959 (3) | 0.040* | |
H20B | 0.9584 (3) | −0.2148 (5) | 0.3663 (3) | 0.040* | |
H20C | 0.8728 (3) | −0.1778 (5) | 0.3082 (3) | 0.040* | |
C21 | 0.8349 (3) | −0.0796 (5) | 0.5192 (3) | 0.0322 (11) | |
H21A | 0.8114 (3) | −0.0229 (5) | 0.5596 (3) | 0.039* | |
H21B | 0.8818 (3) | −0.1398 (5) | 0.5451 (3) | 0.039* | |
H21C | 0.7911 (3) | −0.1432 (5) | 0.4909 (3) | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.0141 (2) | 0.0187 (2) | 0.0119 (2) | 0.00015 (14) | 0.00332 (13) | −0.00071 (13) |
S1 | 0.0236 (6) | 0.0203 (5) | 0.0154 (5) | −0.0016 (4) | 0.0059 (4) | −0.0017 (4) |
P1 | 0.0160 (5) | 0.0185 (6) | 0.0118 (5) | 0.0008 (4) | 0.0035 (4) | 0.0001 (4) |
F1 | 0.068 (2) | 0.0222 (15) | 0.054 (2) | −0.0011 (14) | 0.003 (2) | 0.0083 (13) |
F2 | 0.060 (2) | 0.038 (2) | 0.0276 (15) | −0.0072 (14) | 0.0083 (13) | −0.0211 (12) |
F3 | 0.033 (2) | 0.050 (2) | 0.055 (2) | −0.0173 (14) | 0.0197 (14) | −0.0232 (15) |
O1 | 0.034 (2) | 0.038 (2) | 0.036 (2) | −0.0055 (15) | 0.011 (2) | 0.015 (2) |
O2 | 0.022 (2) | 0.023 (2) | 0.0124 (13) | −0.0021 (12) | 0.0040 (12) | −0.0017 (11) |
O3 | 0.043 (2) | 0.025 (2) | 0.0155 (15) | 0.0033 (14) | 0.0052 (14) | 0.0013 (12) |
O4 | 0.026 (2) | 0.042 (2) | 0.028 (2) | −0.0046 (15) | 0.0137 (14) | −0.0050 (14) |
C1 | 0.018 (2) | 0.026 (2) | 0.024 (2) | 0.001 (2) | 0.003 (2) | −0.003 (2) |
C2 | 0.028 (2) | 0.025 (2) | 0.015 (2) | 0.003 (2) | 0.002 (2) | −0.005 (2) |
C3 | 0.030 (3) | 0.036 (3) | 0.028 (2) | 0.007 (2) | 0.003 (2) | −0.012 (2) |
C4 | 0.050 (3) | 0.021 (2) | 0.028 (2) | −0.005 (2) | 0.008 (2) | −0.012 (2) |
C5 | 0.016 (2) | 0.025 (2) | 0.016 (2) | 0.004 (2) | −0.001 (2) | −0.001 (2) |
C6 | 0.028 (2) | 0.029 (3) | 0.018 (2) | 0.009 (2) | 0.001 (2) | 0.006 (2) |
C7 | 0.026 (2) | 0.028 (2) | 0.022 (2) | −0.001 (2) | −0.002 (2) | −0.003 (2) |
C8 | 0.021 (2) | 0.032 (2) | 0.021 (2) | 0.001 (2) | 0.007 (2) | 0.006 (2) |
C9 | 0.034 (3) | 0.039 (3) | 0.024 (2) | −0.004 (2) | 0.008 (2) | 0.005 (2) |
C10 | 0.028 (3) | 0.029 (3) | 0.027 (2) | −0.007 (2) | 0.007 (2) | 0.004 (2) |
C11 | 0.035 (3) | 0.022 (2) | 0.024 (2) | −0.002 (2) | 0.008 (2) | −0.005 (2) |
C12 | 0.014 (2) | 0.035 (3) | 0.017 (2) | 0.003 (2) | −0.001 (2) | −0.001 (2) |
C13 | 0.018 (2) | 0.028 (2) | 0.021 (2) | −0.002 (2) | 0.003 (2) | −0.002 (2) |
C14 | 0.015 (2) | 0.035 (3) | 0.022 (2) | 0.000 (2) | 0.002 (2) | −0.004 (2) |
C15 | 0.021 (2) | 0.027 (2) | 0.021 (2) | 0.008 (2) | −0.005 (2) | 0.000 (2) |
C16 | 0.018 (2) | 0.026 (2) | 0.016 (2) | 0.004 (2) | −0.002 (2) | 0.003 (2) |
C17 | 0.022 (2) | 0.041 (3) | 0.018 (2) | 0.000 (2) | 0.001 (2) | −0.010 (2) |
C18 | 0.024 (3) | 0.041 (3) | 0.031 (3) | −0.012 (2) | 0.003 (2) | −0.009 (2) |
C19 | 0.020 (3) | 0.062 (3) | 0.033 (3) | −0.002 (2) | 0.010 (2) | −0.012 (2) |
C20 | 0.033 (3) | 0.028 (3) | 0.039 (3) | 0.010 (2) | 0.000 (2) | −0.001 (2) |
C21 | 0.035 (3) | 0.035 (3) | 0.024 (2) | 0.002 (2) | −0.002 (2) | 0.010 (2) |
Ru1—C1 | 1.862 (4) | C7—H7C | 0.98 |
Ru1—O2 | 2.195 (3) | C8—C9 | 1.525 (6) |
Ru1—C13 | 2.198 (4) | C8—C10 | 1.530 (6) |
Ru1—C12 | 2.218 (4) | C8—H8 | 1.00 |
Ru1—C14 | 2.227 (4) | C9—H9A | 0.98 |
Ru1—C15 | 2.261 (4) | C9—H9B | 0.98 |
Ru1—C16 | 2.284 (4) | C9—H9C | 0.98 |
Ru1—P1 | 2.3952 (11) | C10—H10A | 0.98 |
S1—O4 | 1.427 (3) | C10—H10B | 0.98 |
S1—O3 | 1.433 (3) | C10—H10C | 0.98 |
S1—O2 | 1.478 (3) | C12—C16 | 1.439 (6) |
S1—C11 | 1.830 (4) | C12—C13 | 1.443 (6) |
P1—C2 | 1.854 (4) | C12—C17 | 1.507 (6) |
P1—C5 | 1.864 (4) | C13—C14 | 1.438 (6) |
P1—C8 | 1.877 (4) | C13—C18 | 1.500 (6) |
F1—C11 | 1.315 (5) | C14—C15 | 1.423 (6) |
F2—C11 | 1.334 (5) | C14—C19 | 1.513 (6) |
F3—C11 | 1.334 (5) | C15—C16 | 1.422 (6) |
O1—C1 | 1.159 (5) | C15—C20 | 1.503 (6) |
C2—C4 | 1.516 (6) | C16—C21 | 1.499 (6) |
C2—C3 | 1.551 (6) | C17—H17A | 0.98 |
C2—H2 | 1.00 | C17—H17B | 0.98 |
C3—H3A | 0.98 | C17—H17C | 0.98 |
C3—H3B | 0.98 | C18—H18A | 0.98 |
C3—H3C | 0.98 | C18—H18B | 0.98 |
C4—H4A | 0.98 | C18—H18C | 0.98 |
C4—H4B | 0.98 | C19—H19A | 0.98 |
C4—H4C | 0.98 | C19—H19B | 0.98 |
C5—C7 | 1.529 (5) | C19—H19C | 0.98 |
C5—C6 | 1.538 (6) | C20—H20A | 0.98 |
C5—H5 | 1.00 | C20—H20B | 0.98 |
C6—H6A | 0.98 | C20—H20C | 0.98 |
C6—H6B | 0.98 | C21—H21A | 0.98 |
C6—H6C | 0.98 | C21—H21B | 0.98 |
C7—H7A | 0.98 | C21—H21C | 0.98 |
C7—H7B | 0.98 | ||
C1—Ru1—O2 | 96.76 (14) | C9—C8—H8 | 107.0 |
C1—Ru1—C13 | 87.9 (2) | C10—C8—H8 | 107.0 |
O2—Ru1—C13 | 144.71 (13) | P1—C8—H8 | 106.9 |
C1—Ru1—C12 | 118.5 (2) | C8—C9—H9A | 109.5 |
O2—Ru1—C12 | 143.07 (13) | C8—C9—H9B | 109.5 |
C13—Ru1—C12 | 38.15 (15) | H9A—C9—H9B | 109.5 |
C1—Ru1—C14 | 93.5 (2) | C8—C9—H9C | 109.5 |
O2—Ru1—C14 | 106.80 (13) | H9A—C9—H9C | 109.5 |
C13—Ru1—C14 | 37.92 (15) | H9B—C9—H9C | 109.5 |
C12—Ru1—C14 | 63.21 (15) | C8—C10—H10A | 109.5 |
C1—Ru1—C15 | 128.1 (2) | C8—C10—H10B | 109.5 |
O2—Ru1—C15 | 88.39 (13) | H10A—C10—H10B | 109.5 |
C13—Ru1—C15 | 62.3 (2) | C8—C10—H10C | 109.5 |
C12—Ru1—C15 | 62.01 (15) | H10A—C10—H10C | 109.5 |
C14—Ru1—C15 | 37.0 (2) | H10B—C10—H10C | 109.5 |
C1—Ru1—C16 | 150.3 (2) | F1—C11—F3 | 108.2 (4) |
O2—Ru1—C16 | 105.89 (13) | F1—C11—F2 | 108.2 (4) |
C13—Ru1—C16 | 62.52 (15) | F3—C11—F2 | 107.0 (4) |
C12—Ru1—C16 | 37.24 (15) | F1—C11—S1 | 111.5 (3) |
C14—Ru1—C16 | 62.0 (2) | F3—C11—S1 | 111.6 (3) |
C15—Ru1—C16 | 36.47 (14) | F2—C11—S1 | 110.2 (3) |
C1—Ru1—P1 | 91.82 (13) | C16—C12—C13 | 107.7 (4) |
O2—Ru1—P1 | 87.12 (7) | C16—C12—C17 | 125.5 (4) |
C13—Ru1—P1 | 127.81 (11) | C13—C12—C17 | 125.5 (4) |
C12—Ru1—P1 | 101.41 (11) | C16—C12—Ru1 | 73.9 (2) |
C14—Ru1—P1 | 164.38 (11) | C13—C12—Ru1 | 70.2 (2) |
C15—Ru1—P1 | 140.04 (11) | C17—C12—Ru1 | 131.7 (3) |
C16—Ru1—P1 | 108.00 (11) | C14—C13—C12 | 107.9 (4) |
O4—S1—O3 | 116.6 (2) | C14—C13—C18 | 126.1 (4) |
O4—S1—O2 | 115.2 (2) | C12—C13—C18 | 125.5 (4) |
O3—S1—O2 | 113.8 (2) | C14—C13—Ru1 | 72.1 (2) |
O4—S1—C11 | 104.5 (2) | C12—C13—Ru1 | 71.7 (2) |
O3—S1—C11 | 104.7 (2) | C18—C13—Ru1 | 127.8 (3) |
O2—S1—C11 | 99.1 (2) | C15—C14—C13 | 107.4 (4) |
C2—P1—C5 | 103.0 (2) | C15—C14—C19 | 126.8 (4) |
C2—P1—C8 | 103.0 (2) | C13—C14—C19 | 125.6 (4) |
C5—P1—C8 | 100.4 (2) | C15—C14—Ru1 | 72.8 (2) |
C2—P1—Ru1 | 113.23 (14) | C13—C14—Ru1 | 69.9 (2) |
C5—P1—Ru1 | 118.58 (13) | C19—C14—Ru1 | 126.1 (3) |
C8—P1—Ru1 | 116.33 (14) | C14—C15—C16 | 109.4 (4) |
S1—O2—Ru1 | 124.5 (2) | C14—C15—C20 | 126.4 (4) |
O1—C1—Ru1 | 168.2 (4) | C16—C15—C20 | 124.2 (4) |
C4—C2—C3 | 110.1 (4) | C14—C15—Ru1 | 70.2 (2) |
C4—C2—P1 | 114.6 (3) | C16—C15—Ru1 | 72.6 (2) |
C3—C2—P1 | 114.8 (3) | C20—C15—Ru1 | 123.4 (3) |
C4—C2—H2 | 105.4 | C15—C16—C12 | 107.5 (4) |
C3—C2—H2 | 105.4 | C15—C16—C21 | 124.3 (4) |
P1—C2—H2 | 105.4 | C12—C16—C21 | 126.9 (4) |
C2—C3—H3A | 109.5 | C15—C16—Ru1 | 70.9 (2) |
C2—C3—H3B | 109.5 | C12—C16—Ru1 | 68.9 (2) |
H3A—C3—H3B | 109.5 | C21—C16—Ru1 | 135.7 (3) |
C2—C3—H3C | 109.5 | C12—C17—H17A | 109.5 |
H3A—C3—H3C | 109.5 | C12—C17—H17B | 109.5 |
H3B—C3—H3C | 109.5 | H17A—C17—H17B | 109.5 |
C2—C4—H4A | 109.5 | C12—C17—H17C | 109.5 |
C2—C4—H4B | 109.5 | H17A—C17—H17C | 109.5 |
H4A—C4—H4B | 109.5 | H17B—C17—H17C | 109.5 |
C2—C4—H4C | 109.5 | C13—C18—H18A | 109.5 |
H4A—C4—H4C | 109.5 | C13—C18—H18B | 109.5 |
H4B—C4—H4C | 109.5 | H18A—C18—H18B | 109.5 |
C7—C5—C6 | 109.0 (3) | C13—C18—H18C | 109.5 |
C7—C5—P1 | 116.4 (3) | H18A—C18—H18C | 109.5 |
C6—C5—P1 | 113.1 (3) | H18B—C18—H18C | 109.5 |
C7—C5—H5 | 105.8 | C14—C19—H19A | 109.5 |
C6—C5—H5 | 105.8 | C14—C19—H19B | 109.5 |
P1—C5—H5 | 105.8 | H19A—C19—H19B | 109.5 |
C5—C6—H6A | 109.5 | C14—C19—H19C | 109.5 |
C5—C6—H6B | 109.5 | H19A—C19—H19C | 109.5 |
H6A—C6—H6B | 109.5 | H19B—C19—H19C | 109.5 |
C5—C6—H6C | 109.5 | C15—C20—H20A | 109.5 |
H6A—C6—H6C | 109.5 | C15—C20—H20B | 109.5 |
H6B—C6—H6C | 109.5 | H20A—C20—H20B | 109.5 |
C5—C7—H7A | 109.5 | C15—C20—H20C | 109.5 |
C5—C7—H7B | 109.5 | H20A—C20—H20C | 109.5 |
H7A—C7—H7B | 109.5 | H20B—C20—H20C | 109.5 |
C5—C7—H7C | 109.5 | C16—C21—H21A | 109.5 |
H7A—C7—H7C | 109.5 | C16—C21—H21B | 109.5 |
H7B—C7—H7C | 109.5 | H21A—C21—H21B | 109.5 |
C9—C8—C10 | 109.8 (4) | C16—C21—H21C | 109.5 |
C9—C8—P1 | 114.3 (3) | H21A—C21—H21C | 109.5 |
C10—C8—P1 | 111.5 (3) | H21B—C21—H21C | 109.5 |
C1—Ru1—P1—C2 | −77.6 (2) | C15—Ru1—C13—C12 | −79.1 (3) |
O2—Ru1—P1—C2 | −174.3 (2) | C16—Ru1—C13—C12 | −37.8 (2) |
C13—Ru1—P1—C2 | 11.1 (2) | P1—Ru1—C13—C12 | 54.4 (3) |
C12—Ru1—P1—C2 | 41.9 (2) | C1—Ru1—C13—C18 | 23.9 (4) |
C14—Ru1—P1—C2 | 32.2 (5) | O2—Ru1—C13—C18 | 122.7 (3) |
C15—Ru1—P1—C2 | 101.6 (2) | C12—Ru1—C13—C18 | −121.1 (5) |
C16—Ru1—P1—C2 | 79.9 (2) | C14—Ru1—C13—C18 | 122.3 (5) |
C1—Ru1—P1—C5 | 43.3 (2) | C15—Ru1—C13—C18 | 159.8 (4) |
O2—Ru1—P1—C5 | −53.4 (2) | C16—Ru1—C13—C18 | −158.9 (4) |
C13—Ru1—P1—C5 | 132.0 (2) | P1—Ru1—C13—C18 | −66.8 (4) |
C12—Ru1—P1—C5 | 162.8 (2) | C12—C13—C14—C15 | −0.5 (5) |
C14—Ru1—P1—C5 | 153.1 (5) | C18—C13—C14—C15 | 172.1 (4) |
C15—Ru1—P1—C5 | −137.5 (2) | Ru1—C13—C14—C15 | −63.6 (3) |
C16—Ru1—P1—C5 | −159.2 (2) | C12—C13—C14—C19 | −176.2 (4) |
C1—Ru1—P1—C8 | 163.3 (2) | C18—C13—C14—C19 | −3.6 (7) |
O2—Ru1—P1—C8 | 66.6 (2) | Ru1—C13—C14—C19 | 120.6 (4) |
C13—Ru1—P1—C8 | −108.0 (2) | C12—C13—C14—Ru1 | 63.2 (3) |
C12—Ru1—P1—C8 | −77.2 (2) | C18—C13—C14—Ru1 | −124.2 (4) |
C14—Ru1—P1—C8 | −86.9 (5) | C1—Ru1—C14—C15 | −161.4 (3) |
C15—Ru1—P1—C8 | −17.5 (2) | O2—Ru1—C14—C15 | −63.3 (2) |
C16—Ru1—P1—C8 | −39.2 (2) | C13—Ru1—C14—C15 | 116.5 (3) |
O4—S1—O2—Ru1 | 58.5 (2) | C12—Ru1—C14—C15 | 78.3 (3) |
O3—S1—O2—Ru1 | −80.0 (2) | C16—Ru1—C14—C15 | 36.1 (2) |
C11—S1—O2—Ru1 | 169.4 (2) | P1—Ru1—C14—C15 | 89.0 (5) |
C1—Ru1—O2—S1 | 32.7 (2) | C1—Ru1—C14—C13 | 82.1 (3) |
C13—Ru1—O2—S1 | −63.2 (3) | O2—Ru1—C14—C13 | −179.8 (2) |
C12—Ru1—O2—S1 | −130.5 (2) | C12—Ru1—C14—C13 | −38.2 (2) |
C14—Ru1—O2—S1 | −63.0 (2) | C15—Ru1—C14—C13 | −116.5 (3) |
C15—Ru1—O2—S1 | −95.5 (2) | C16—Ru1—C14—C13 | −80.4 (3) |
C16—Ru1—O2—S1 | −127.9 (2) | P1—Ru1—C14—C13 | −27.5 (6) |
P1—Ru1—O2—S1 | 124.2 (2) | C1—Ru1—C14—C19 | −38.0 (4) |
O2—Ru1—C1—O1 | −126.5 (18) | O2—Ru1—C14—C19 | 60.1 (4) |
C13—Ru1—C1—O1 | 18.4 (18) | C13—Ru1—C14—C19 | −120.1 (5) |
C12—Ru1—C1—O1 | 42.1 (19) | C12—Ru1—C14—C19 | −158.3 (4) |
C14—Ru1—C1—O1 | −19.1 (18) | C15—Ru1—C14—C19 | 123.4 (5) |
C15—Ru1—C1—O1 | −33.3 (19) | C16—Ru1—C14—C19 | 159.5 (4) |
C16—Ru1—C1—O1 | 13 (2) | P1—Ru1—C14—C19 | −147.6 (3) |
P1—Ru1—C1—O1 | 146.2 (18) | C13—C14—C15—C16 | −0.7 (5) |
C5—P1—C2—C4 | −81.0 (3) | C19—C14—C15—C16 | 175.0 (4) |
C8—P1—C2—C4 | 174.9 (3) | Ru1—C14—C15—C16 | −62.4 (3) |
Ru1—P1—C2—C4 | 48.4 (3) | C13—C14—C15—C20 | 179.2 (4) |
C5—P1—C2—C3 | 48.0 (3) | C19—C14—C15—C20 | −5.1 (7) |
C8—P1—C2—C3 | −56.2 (3) | Ru1—C14—C15—C20 | 117.5 (4) |
Ru1—P1—C2—C3 | 177.3 (3) | C13—C14—C15—Ru1 | 61.8 (3) |
C2—P1—C5—C7 | −153.4 (3) | C19—C14—C15—Ru1 | −122.6 (4) |
C8—P1—C5—C7 | −47.3 (3) | C1—Ru1—C15—C14 | 23.9 (3) |
Ru1—P1—C5—C7 | 80.6 (3) | O2—Ru1—C15—C14 | 121.2 (2) |
C2—P1—C5—C6 | 79.1 (3) | C13—Ru1—C15—C14 | −38.4 (2) |
C8—P1—C5—C6 | −174.7 (3) | C12—Ru1—C15—C14 | −81.8 (3) |
Ru1—P1—C5—C6 | −46.9 (3) | C16—Ru1—C15—C14 | −118.9 (4) |
C2—P1—C8—C9 | −38.5 (4) | P1—Ru1—C15—C14 | −155.2 (2) |
C5—P1—C8—C9 | −144.6 (3) | C1—Ru1—C15—C16 | 142.7 (3) |
Ru1—P1—C8—C9 | 86.0 (3) | O2—Ru1—C15—C16 | −119.9 (2) |
C2—P1—C8—C10 | −163.7 (3) | C13—Ru1—C15—C16 | 80.5 (3) |
C5—P1—C8—C10 | 90.2 (3) | C12—Ru1—C15—C16 | 37.1 (2) |
Ru1—P1—C8—C10 | −39.2 (3) | C14—Ru1—C15—C16 | 118.9 (4) |
O4—S1—C11—F1 | 51.8 (3) | C16—Ru1—C15—C16 | 0.000 (1) |
O3—S1—C11—F1 | 174.9 (3) | P1—Ru1—C15—C16 | −36.3 (3) |
O2—S1—C11—F1 | −67.4 (3) | C1—Ru1—C15—C20 | −97.4 (4) |
O4—S1—C11—F3 | 172.8 (3) | O2—Ru1—C15—C20 | 0.0 (4) |
O3—S1—C11—F3 | −64.0 (3) | C13—Ru1—C15—C20 | −159.6 (4) |
O2—S1—C11—F3 | 53.7 (3) | C12—Ru1—C15—C20 | 157.0 (4) |
O4—S1—C11—F2 | −68.4 (3) | C14—Ru1—C15—C20 | −121.2 (5) |
O3—S1—C11—F2 | 54.7 (3) | C16—Ru1—C15—C20 | 119.9 (5) |
O2—S1—C11—F2 | 172.4 (3) | P1—Ru1—C15—C20 | 83.6 (4) |
C1—Ru1—C12—C16 | −156.8 (2) | C14—C15—C16—C12 | 1.5 (5) |
O2—Ru1—C12—C16 | 4.2 (3) | C20—C15—C16—C12 | −178.4 (4) |
C13—Ru1—C12—C16 | −116.1 (3) | Ru1—C15—C16—C12 | −59.4 (3) |
C14—Ru1—C12—C16 | −78.1 (3) | C14—C15—C16—C21 | −166.3 (4) |
C15—Ru1—C12—C16 | −36.3 (2) | C20—C15—C16—C21 | 13.8 (6) |
P1—Ru1—C12—C16 | 104.8 (2) | Ru1—C15—C16—C21 | 132.8 (4) |
C1—Ru1—C12—C13 | −40.6 (3) | C14—C15—C16—Ru1 | 60.9 (3) |
O2—Ru1—C12—C13 | 120.4 (3) | C20—C15—C16—Ru1 | −119.0 (4) |
C14—Ru1—C12—C13 | 38.0 (2) | C13—C12—C16—C15 | −1.8 (4) |
C15—Ru1—C12—C13 | 79.8 (3) | C17—C12—C16—C15 | −169.2 (4) |
C16—Ru1—C12—C13 | 116.1 (3) | Ru1—C12—C16—C15 | 60.7 (3) |
P1—Ru1—C12—C13 | −139.1 (2) | C13—C12—C16—C21 | 165.6 (4) |
C1—Ru1—C12—C17 | 79.7 (4) | C17—C12—C16—C21 | −1.8 (7) |
O2—Ru1—C12—C17 | −119.3 (4) | Ru1—C12—C16—C21 | −132.0 (4) |
C13—Ru1—C12—C17 | 120.3 (5) | C13—C12—C16—Ru1 | −62.4 (3) |
C14—Ru1—C12—C17 | 158.3 (5) | C17—C12—C16—Ru1 | 130.2 (4) |
C15—Ru1—C12—C17 | −159.9 (5) | C1—Ru1—C16—C15 | −74.0 (4) |
C16—Ru1—C12—C17 | −123.6 (5) | O2—Ru1—C16—C15 | 64.3 (3) |
P1—Ru1—C12—C17 | −18.8 (4) | C13—Ru1—C16—C15 | −79.7 (3) |
C16—C12—C13—C14 | 1.4 (4) | C12—Ru1—C16—C15 | −118.4 (4) |
C17—C12—C13—C14 | 168.8 (4) | C14—Ru1—C16—C15 | −36.6 (2) |
Ru1—C12—C13—C14 | −63.5 (3) | P1—Ru1—C16—C15 | 156.4 (2) |
C16—C12—C13—C18 | −171.3 (4) | C1—Ru1—C16—C12 | 44.4 (4) |
C17—C12—C13—C18 | −3.8 (7) | O2—Ru1—C16—C12 | −177.4 (2) |
Ru1—C12—C13—C18 | 123.9 (4) | C13—Ru1—C16—C12 | 38.7 (2) |
C16—C12—C13—Ru1 | 64.9 (3) | C14—Ru1—C16—C12 | 81.8 (3) |
C17—C12—C13—Ru1 | −127.7 (4) | C15—Ru1—C16—C12 | 118.4 (4) |
C1—Ru1—C13—C14 | −98.4 (3) | P1—Ru1—C16—C12 | −85.2 (2) |
O2—Ru1—C13—C14 | 0.4 (4) | C1—Ru1—C16—C21 | 166.0 (4) |
C12—Ru1—C13—C14 | 116.6 (4) | O2—Ru1—C16—C21 | −55.7 (4) |
C15—Ru1—C13—C14 | 37.4 (2) | C13—Ru1—C16—C21 | 160.3 (5) |
C16—Ru1—C13—C14 | 78.8 (3) | C12—Ru1—C16—C21 | 121.7 (5) |
P1—Ru1—C13—C14 | 170.9 (2) | C14—Ru1—C16—C21 | −156.6 (5) |
C1—Ru1—C13—C12 | 145.1 (3) | C15—Ru1—C16—C21 | −120.0 (5) |
O2—Ru1—C13—C12 | −116.2 (3) | P1—Ru1—C16—C21 | 36.5 (4) |
C14—Ru1—C13—C12 | −116.6 (4) |
Experimental details
Crystal data | |
Chemical formula | [Ru(CF3O3S)(C10H15)(C9H21P)(CO)] |
Mr | 573.60 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 128 |
a, b, c (Å) | 16.056 (1), 9.1258 (5), 17.005 (1) |
β (°) | 98.796 (1) |
V (Å3) | 2462.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.83 |
Crystal size (mm) | 0.27 × 0.13 × 0.08 |
Data collection | |
Diffractometer | SMART CCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (Blessing, 1995) |
Tmin, Tmax | 0.81, 0.91 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10547, 4036, 3238 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.587 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.089, 1.05 |
No. of reflections | 4035 |
No. of parameters | 280 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.71 |
Computer programs: SMART (Bruker, 1999), SAINT (Siemens, 1995), SAINT, SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1995), TEXSAN (Molecular Structure Corporation, 1992), SHELXL97.
Ru1—C1 | 1.862 (4) | Ru1—C14 | 2.227 (4) |
Ru1—O2 | 2.195 (3) | Ru1—C15 | 2.261 (4) |
Ru1—C13 | 2.198 (4) | Ru1—C16 | 2.284 (4) |
Ru1—C12 | 2.218 (4) | Ru1—P1 | 2.3952 (11) |
C1—Ru1—O2 | 96.76 (14) | O2—Ru1—P1 | 87.12 (7) |
C1—Ru1—P1 | 91.82 (13) |
Monocyclopentadienyl complexes of group VIII transition metals are of interest because of their participation in a variety of important stoichiometric and catalytic processes. Especially of interest are those group VIII complexes with highly labile substituents, such as trifluoromethanesulfonate groups, since such groups can easily generate a vacant coordination site during chemical reactions.
In the compound studied, the Ru atom is coordinated in a `three-legged piano-stool' fashion by one O atom of the trifluoromethanesulfonate, a carbonyl, a triisopropylphosphine, and a pentamethylcyclopentadienyl (Cp*). An examination of the Cambridge Structural Database (CSD; Allen & Kennard, 1993) reveals that even though there exist numerous cationic species containing Cp or Cp*, a P(iPr)3 and a carbonyl ligand; there are only four neutral species. The distance between the Ru atom and the coordinated O atom of the trifluoromethanesulfonate [2.195 (3) Å] is longer than that of most Ru—O distances in similar Ru–trifluoromethanesulfonate compounds [2.125 (5)–2.177 (4) Å; Gemel et al., 1997; Svetlanova-Larsen et al., 1996; Burns & Hubbard, 1994; Ontko et al., 1998]; only one of six compounds had a longer distance [2.277 (2) Å; Mauthner et al., 1997]. The Ru—P bond distance [2.395 (1) Å] is comparable with that found in similar Cp*–Ru–carbonyl–triisopropylphosphine complexes (typically 2.39 Å; Campion et al., 1988; Bernad et al., 2000). The Ru—CCp* bond distances [2.203 (4)–2.287 (4) Å] are within the expected range for half-sandwich RuII compounds (Johnson et al., 1995).