Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113005489/dt3019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005489/dt3019Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005489/dt3019IIsup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108270113005489/dt3019sup4.pdf | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108270113005489/dt3019sup5.pdf | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108270113005489/dt3019sup6.pdf |
CCDC references: 934600; 934601
For both compounds, data collection: P3/P4-PC (Siemens, 1991); cell refinement: P3/P4-PC (Siemens, 1991); data reduction: P3/P4-PC (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-NT (Sheldrick, 2008); software used to prepare material for publication: SHELXTL-NT (Sheldrick, 2008) and PLATON (Spek, 2009).
[Ru(C31H21P)(CO)3] | F(000) = 1232 |
Mr = 609.55 | Dx = 1.481 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 10.029 (7) Å | θ = 5–12.5° |
b = 15.242 (5) Å | µ = 0.67 mm−1 |
c = 17.922 (5) Å | T = 295 K |
β = 93.50 (5)° | Needle, colourless |
V = 2735 (2) Å3 | 0.28 × 0.10 × 0.08 mm |
Z = 4 |
Siemens R3m diffractometer | 2864 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.060 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
ω/2θ scans | h = −11→11 |
Absorption correction: ψ scan (XEMP in SHELXTL-NT; Sheldrick, 2008) | k = −1→18 |
Tmin = 0.90, Tmax = 0.94 | l = −1→21 |
4957 measured reflections | 2 standard reflections every 98 reflections |
4799 independent reflections | intensity decay: 1% |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2))2 + 4.5949P] where P = (Fo2 + 2Fc2)/3 |
4799 reflections | (Δ/σ)max < 0.001 |
352 parameters | Δρmax = 0.44 e Å−3 |
124 restraints | Δρmin = −0.46 e Å−3 |
Experimental. Spectroscopic data for (I): IR data [cyclohexane, ν(CO), cm-1]: 2080m, 2024s, 2000ms; 1H NMR (acetone-d6, δ, p.p.m.): 8.10d (2H), 7.99d (2H), 7.23dd (2H), 6.93dd (2H), 6.38d (2H), 7.38dd (2H), 7.31dd (2H), 7.59dd (2H), 7.14dd (2H), 7.50dd (2H), 7.65dd (1H); 31P NMR data for (I) (δ, p.p.m.): 11.9. |
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. |
x | y | z | Uiso*/Ueq | ||
Ru1 | 0.16017 (5) | 0.51744 (3) | 0.16295 (3) | 0.03182 (13) | |
P1 | 0.03200 (18) | 0.43142 (11) | 0.28827 (9) | 0.0347 (4) | |
C1 | 0.2871 (7) | 0.6082 (5) | 0.1520 (3) | 0.0480 (18) | |
O1 | 0.3668 (5) | 0.6595 (3) | 0.1462 (3) | 0.0682 (15) | |
C2 | 0.0413 (7) | 0.5667 (4) | 0.0845 (3) | 0.0477 (17) | |
O2 | −0.0304 (5) | 0.6020 (3) | 0.0412 (2) | 0.0630 (15) | |
C3 | 0.2557 (7) | 0.4350 (5) | 0.0998 (3) | 0.0437 (17) | |
O3 | 0.3083 (5) | 0.3909 (3) | 0.0638 (3) | 0.0613 (15) | |
C11 | −0.0641 (7) | 0.3669 (4) | 0.3508 (4) | 0.0381 (16) | |
C21 | −0.1521 (7) | 0.3057 (4) | 0.3215 (3) | 0.0398 (16) | |
H21 | −0.1595 | 0.2968 | 0.2701 | 0.048* | |
C31 | −0.2296 (7) | 0.2572 (4) | 0.3666 (4) | 0.058 (2) | |
H31 | −0.2869 | 0.2142 | 0.3464 | 0.070* | |
C41 | −0.2207 (7) | 0.2735 (4) | 0.4433 (4) | 0.0546 (19) | |
H41 | −0.2761 | 0.2432 | 0.4742 | 0.066* | |
C51 | −0.1319 (7) | 0.3332 (5) | 0.4738 (4) | 0.066 (2) | |
H51 | −0.1223 | 0.3412 | 0.5253 | 0.079* | |
C61 | −0.0566 (6) | 0.3818 (4) | 0.4267 (3) | 0.0476 (18) | |
H61 | 0.0001 | 0.4252 | 0.4466 | 0.057* | |
C4 | 0.0064 (6) | 0.4105 (4) | 0.1911 (3) | 0.0339 (14) | |
C12 | −0.1288 (6) | 0.4287 (4) | 0.1550 (3) | 0.0349 (14) | |
C22 | −0.2191 (5) | 0.4997 (4) | 0.1589 (3) | 0.0424 (16) | |
H22 | −0.2018 | 0.5447 | 0.1931 | 0.051* | |
C32 | −0.3338 (6) | 0.5017 (4) | 0.1114 (3) | 0.0558 (19) | |
H32 | −0.3916 | 0.5493 | 0.1132 | 0.067* | |
C42 | −0.3637 (6) | 0.4342 (5) | 0.0614 (4) | 0.055 (2) | |
H42 | −0.4418 | 0.4359 | 0.0306 | 0.066* | |
C52 | −0.2777 (6) | 0.3653 (4) | 0.0578 (3) | 0.0381 (15) | |
H52 | −0.2975 | 0.3200 | 0.0241 | 0.046* | |
C62 | −0.1637 (5) | 0.3614 (4) | 0.1024 (3) | 0.0311 (14) | |
C13 | 0.0362 (5) | 0.3228 (3) | 0.1633 (3) | 0.0242 (13) | |
C23 | 0.1451 (6) | 0.2648 (3) | 0.1809 (3) | 0.0311 (15) | |
H23 | 0.2134 | 0.2822 | 0.2151 | 0.037* | |
C33 | 0.1506 (8) | 0.1825 (4) | 0.1475 (3) | 0.0531 (19) | |
H33 | 0.2204 | 0.1442 | 0.1603 | 0.064* | |
C43 | 0.0504 (7) | 0.1588 (4) | 0.0950 (3) | 0.0525 (19) | |
H43 | 0.0553 | 0.1041 | 0.0723 | 0.063* | |
C53 | −0.0558 (6) | 0.2119 (4) | 0.0749 (3) | 0.0381 (16) | |
H53 | −0.1209 | 0.1944 | 0.0388 | 0.046* | |
C63 | −0.0634 (5) | 0.2940 (4) | 0.1106 (3) | 0.0269 (13) | |
C14 | −0.0030 (6) | 0.5449 (3) | 0.2964 (3) | 0.0315 (14) | |
C24 | 0.0612 (5) | 0.5927 (3) | 0.2403 (3) | 0.0243 (12) | |
C34 | 0.0368 (6) | 0.6837 (4) | 0.2427 (3) | 0.0405 (17) | |
H34 | 0.0745 | 0.7191 | 0.2073 | 0.049* | |
C44 | −0.0414 (6) | 0.7241 (4) | 0.2955 (3) | 0.0406 (16) | |
H44 | −0.0549 | 0.7844 | 0.2946 | 0.049* | |
C54 | −0.0980 (7) | 0.6724 (4) | 0.3488 (3) | 0.049 (2) | |
H54 | −0.1468 | 0.6988 | 0.3851 | 0.059* | |
C64 | −0.0831 (7) | 0.5830 (5) | 0.3486 (4) | 0.0504 (19) | |
H64 | −0.1256 | 0.5484 | 0.3827 | 0.060* | |
C15 | 0.2087 (6) | 0.4214 (4) | 0.3090 (3) | 0.0305 (14) | |
C25 | 0.2783 (5) | 0.4651 (4) | 0.2556 (3) | 0.0314 (14) | |
C35 | 0.4162 (6) | 0.4629 (4) | 0.2661 (3) | 0.0398 (16) | |
H35 | 0.4673 | 0.4894 | 0.2308 | 0.048* | |
C45 | 0.4795 (7) | 0.4228 (4) | 0.3267 (4) | 0.0504 (18) | |
H45 | 0.5723 | 0.4238 | 0.3324 | 0.060* | |
C55 | 0.4081 (7) | 0.3812 (4) | 0.3791 (3) | 0.0488 (19) | |
H55 | 0.4526 | 0.3537 | 0.4196 | 0.059* | |
C65 | 0.2699 (7) | 0.3801 (4) | 0.3718 (3) | 0.0439 (17) | |
H65 | 0.2198 | 0.3530 | 0.4073 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.0310 (3) | 0.0318 (2) | 0.0328 (2) | −0.0008 (3) | 0.00334 (19) | 0.0045 (3) |
P1 | 0.0393 (11) | 0.0309 (10) | 0.0343 (10) | −0.0036 (8) | 0.0050 (8) | 0.0004 (8) |
C1 | 0.055 (5) | 0.061 (5) | 0.029 (4) | −0.006 (4) | 0.009 (3) | 0.013 (3) |
O1 | 0.062 (4) | 0.049 (3) | 0.093 (4) | −0.022 (3) | 0.008 (3) | 0.003 (3) |
C2 | 0.053 (5) | 0.049 (4) | 0.041 (4) | 0.012 (3) | 0.003 (3) | 0.004 (3) |
O2 | 0.051 (4) | 0.073 (4) | 0.062 (3) | 0.006 (3) | −0.011 (3) | 0.015 (3) |
C3 | 0.045 (4) | 0.062 (5) | 0.025 (3) | −0.017 (3) | 0.009 (3) | −0.001 (3) |
O3 | 0.064 (4) | 0.052 (3) | 0.068 (4) | −0.012 (3) | 0.010 (3) | −0.025 (3) |
C11 | 0.048 (4) | 0.023 (4) | 0.044 (4) | 0.003 (3) | 0.013 (3) | −0.001 (3) |
C21 | 0.052 (4) | 0.039 (4) | 0.028 (4) | −0.001 (3) | −0.001 (3) | −0.005 (3) |
C31 | 0.073 (6) | 0.047 (5) | 0.057 (4) | −0.020 (4) | 0.028 (4) | 0.003 (4) |
C41 | 0.047 (5) | 0.057 (5) | 0.063 (4) | −0.003 (4) | 0.024 (4) | 0.017 (4) |
C51 | 0.068 (6) | 0.087 (6) | 0.043 (4) | −0.017 (5) | −0.002 (4) | 0.018 (4) |
C61 | 0.048 (4) | 0.056 (5) | 0.037 (3) | −0.020 (4) | −0.009 (3) | −0.005 (3) |
C4 | 0.030 (3) | 0.032 (3) | 0.038 (3) | −0.012 (3) | −0.010 (3) | −0.009 (3) |
C12 | 0.029 (3) | 0.040 (4) | 0.036 (3) | −0.007 (3) | −0.001 (3) | 0.012 (3) |
C22 | 0.036 (4) | 0.038 (5) | 0.053 (4) | −0.012 (3) | 0.001 (3) | 0.011 (3) |
C32 | 0.050 (4) | 0.043 (5) | 0.073 (5) | 0.009 (4) | −0.004 (3) | 0.024 (3) |
C42 | 0.025 (4) | 0.066 (5) | 0.072 (5) | −0.006 (4) | −0.014 (4) | 0.021 (4) |
C52 | 0.035 (4) | 0.050 (4) | 0.030 (3) | −0.023 (3) | 0.006 (3) | 0.019 (3) |
C62 | 0.021 (3) | 0.037 (3) | 0.035 (3) | −0.012 (3) | −0.005 (3) | 0.020 (3) |
C13 | 0.028 (3) | 0.030 (3) | 0.014 (3) | −0.001 (2) | −0.006 (2) | 0.009 (2) |
C23 | 0.024 (3) | 0.025 (3) | 0.044 (4) | −0.003 (3) | 0.002 (3) | 0.003 (3) |
C33 | 0.074 (5) | 0.035 (4) | 0.049 (5) | 0.012 (4) | −0.004 (4) | −0.001 (3) |
C43 | 0.070 (5) | 0.048 (4) | 0.040 (4) | 0.004 (4) | 0.006 (4) | −0.007 (3) |
C53 | 0.038 (4) | 0.053 (4) | 0.023 (3) | 0.000 (3) | 0.002 (3) | −0.021 (3) |
C63 | 0.019 (3) | 0.039 (3) | 0.023 (3) | −0.005 (3) | 0.001 (2) | 0.008 (3) |
C14 | 0.032 (4) | 0.025 (3) | 0.036 (3) | −0.001 (3) | −0.010 (3) | −0.005 (2) |
C24 | 0.017 (3) | 0.025 (3) | 0.031 (3) | −0.005 (2) | 0.000 (2) | 0.003 (2) |
C34 | 0.058 (5) | 0.029 (3) | 0.034 (4) | 0.014 (3) | −0.001 (3) | 0.008 (3) |
C44 | 0.041 (4) | 0.039 (4) | 0.042 (4) | 0.015 (3) | 0.002 (3) | −0.008 (3) |
C54 | 0.066 (6) | 0.055 (4) | 0.027 (4) | 0.003 (4) | 0.001 (3) | −0.019 (3) |
C64 | 0.044 (5) | 0.050 (4) | 0.058 (5) | 0.001 (4) | 0.008 (4) | 0.001 (4) |
C15 | 0.032 (3) | 0.032 (4) | 0.026 (3) | −0.008 (3) | −0.009 (3) | −0.004 (3) |
C25 | 0.028 (3) | 0.035 (4) | 0.032 (3) | 0.007 (3) | 0.010 (2) | −0.001 (3) |
C35 | 0.036 (3) | 0.024 (4) | 0.060 (4) | 0.004 (3) | 0.008 (3) | 0.009 (3) |
C45 | 0.032 (4) | 0.064 (5) | 0.053 (4) | −0.008 (4) | −0.012 (3) | −0.007 (4) |
C55 | 0.064 (5) | 0.060 (5) | 0.020 (4) | −0.005 (4) | −0.014 (3) | 0.001 (3) |
C65 | 0.052 (4) | 0.047 (4) | 0.034 (4) | −0.005 (4) | 0.010 (3) | −0.009 (3) |
Ru1—C1 | 1.898 (7) | C52—C62 | 1.355 (7) |
Ru1—C2 | 1.938 (7) | C52—H52 | 0.9300 |
Ru1—C3 | 1.977 (7) | C62—C63 | 1.439 (7) |
Ru1—C24 | 2.095 (5) | C13—C63 | 1.402 (7) |
Ru1—C25 | 2.134 (5) | C13—C23 | 1.426 (7) |
Ru1—C4 | 2.320 (6) | C23—C33 | 1.393 (7) |
P1—C14 | 1.772 (5) | C23—H23 | 0.9300 |
P1—C4 | 1.774 (6) | C33—C43 | 1.382 (8) |
P1—C15 | 1.795 (6) | C33—H33 | 0.9300 |
P1—C11 | 1.812 (6) | C43—C53 | 1.369 (8) |
C1—O1 | 1.128 (7) | C43—H43 | 0.9300 |
C2—O2 | 1.158 (7) | C53—C63 | 1.409 (7) |
C3—O3 | 1.091 (7) | C53—H53 | 0.9300 |
C11—C21 | 1.367 (8) | C14—C64 | 1.397 (8) |
C11—C61 | 1.376 (7) | C14—C24 | 1.427 (7) |
C21—C31 | 1.371 (8) | C24—C34 | 1.410 (7) |
C21—H21 | 0.9300 | C34—C44 | 1.406 (7) |
C31—C41 | 1.396 (8) | C34—H34 | 0.9300 |
C31—H31 | 0.9300 | C44—C54 | 1.386 (8) |
C41—C51 | 1.364 (9) | C44—H44 | 0.9300 |
C41—H41 | 0.9300 | C54—C64 | 1.371 (8) |
C51—C61 | 1.381 (8) | C54—H54 | 0.9300 |
C51—H51 | 0.9300 | C64—H64 | 0.9300 |
C61—H61 | 0.9300 | C15—C25 | 1.390 (7) |
C4—C13 | 1.463 (7) | C15—C65 | 1.398 (7) |
C4—C12 | 1.492 (8) | C25—C35 | 1.385 (7) |
C12—C22 | 1.415 (8) | C35—C45 | 1.368 (8) |
C12—C62 | 1.422 (7) | C35—H35 | 0.9300 |
C22—C32 | 1.390 (7) | C45—C55 | 1.371 (8) |
C22—H22 | 0.9300 | C45—H45 | 0.9300 |
C32—C42 | 1.384 (8) | C55—C65 | 1.384 (9) |
C32—H32 | 0.9300 | C55—H55 | 0.9300 |
C42—C52 | 1.364 (8) | C65—H65 | 0.9300 |
C42—H42 | 0.9300 | ||
C1—Ru1—C2 | 91.7 (3) | C62—C52—C42 | 121.2 (6) |
C1—Ru1—C3 | 93.0 (3) | C62—C52—H52 | 119.4 |
C2—Ru1—C3 | 97.4 (3) | C42—C52—H52 | 119.4 |
C1—Ru1—C24 | 91.0 (2) | C52—C62—C12 | 121.7 (6) |
C2—Ru1—C24 | 88.4 (2) | C52—C62—C63 | 130.5 (6) |
C3—Ru1—C24 | 172.8 (2) | C12—C62—C63 | 107.7 (5) |
C1—Ru1—C25 | 90.5 (2) | C63—C13—C23 | 117.4 (5) |
C2—Ru1—C25 | 175.2 (2) | C63—C13—C4 | 111.3 (5) |
C3—Ru1—C25 | 86.7 (2) | C23—C13—C4 | 131.3 (5) |
C24—Ru1—C25 | 87.3 (2) | C33—C23—C13 | 120.9 (6) |
C1—Ru1—C4 | 173.3 (2) | C33—C23—H23 | 119.5 |
C2—Ru1—C4 | 92.4 (3) | C13—C23—H23 | 119.5 |
C3—Ru1—C4 | 91.7 (2) | C43—C33—C23 | 118.8 (7) |
C24—Ru1—C4 | 83.9 (2) | C43—C33—H33 | 120.6 |
C25—Ru1—C4 | 85.0 (2) | C23—C33—H33 | 120.6 |
C14—P1—C4 | 103.8 (3) | C53—C43—C33 | 123.1 (6) |
C14—P1—C15 | 105.3 (3) | C53—C43—H43 | 118.5 |
C4—P1—C15 | 105.7 (3) | C33—C43—H43 | 118.5 |
C14—P1—C11 | 111.3 (3) | C43—C53—C63 | 118.0 (6) |
C4—P1—C11 | 117.4 (3) | C43—C53—H53 | 121.0 |
C15—P1—C11 | 112.4 (3) | C63—C53—H53 | 121.0 |
O1—C1—Ru1 | 177.0 (7) | C13—C63—C53 | 121.8 (5) |
O2—C2—Ru1 | 174.6 (6) | C13—C63—C62 | 108.1 (5) |
O3—C3—Ru1 | 178.4 (6) | C53—C63—C62 | 130.1 (5) |
C21—C11—C61 | 119.2 (6) | C64—C14—C24 | 124.2 (5) |
C21—C11—P1 | 119.2 (5) | C64—C14—P1 | 125.9 (5) |
C61—C11—P1 | 121.5 (5) | C24—C14—P1 | 109.9 (4) |
C11—C21—C31 | 121.2 (6) | C34—C24—C14 | 113.2 (5) |
C11—C21—H21 | 119.4 | C34—C24—Ru1 | 130.5 (4) |
C31—C21—H21 | 119.4 | C14—C24—Ru1 | 116.0 (4) |
C21—C31—C41 | 118.7 (7) | C44—C34—C24 | 123.8 (6) |
C21—C31—H31 | 120.7 | C44—C34—H34 | 118.1 |
C41—C31—H31 | 120.7 | C24—C34—H34 | 118.1 |
C51—C41—C31 | 120.9 (6) | C54—C44—C34 | 118.9 (6) |
C51—C41—H41 | 119.5 | C54—C44—H44 | 120.5 |
C31—C41—H41 | 119.5 | C34—C44—H44 | 120.5 |
C41—C51—C61 | 118.8 (7) | C64—C54—C44 | 121.0 (6) |
C41—C51—H51 | 120.6 | C64—C54—H54 | 119.5 |
C61—C51—H51 | 120.6 | C44—C54—H54 | 119.5 |
C11—C61—C51 | 121.1 (6) | C54—C64—C14 | 118.8 (6) |
C11—C61—H61 | 119.4 | C54—C64—H64 | 120.6 |
C51—C61—H61 | 119.4 | C14—C64—H64 | 120.6 |
C13—C4—C12 | 102.8 (5) | C25—C15—C65 | 123.8 (6) |
C13—C4—P1 | 118.6 (4) | C25—C15—P1 | 110.3 (4) |
C12—C4—P1 | 117.7 (4) | C65—C15—P1 | 125.8 (5) |
C13—C4—Ru1 | 114.5 (4) | C35—C25—C15 | 115.7 (5) |
C12—C4—Ru1 | 112.0 (4) | C35—C25—Ru1 | 128.1 (4) |
P1—C4—Ru1 | 91.6 (2) | C15—C25—Ru1 | 115.9 (4) |
C22—C12—C62 | 116.8 (5) | C45—C35—C25 | 122.0 (6) |
C22—C12—C4 | 133.5 (6) | C45—C35—H35 | 119.0 |
C62—C12—C4 | 109.5 (5) | C25—C35—H35 | 119.0 |
C32—C22—C12 | 119.7 (6) | C35—C45—C55 | 120.9 (6) |
C32—C22—H22 | 120.2 | C35—C45—H45 | 119.5 |
C12—C22—H22 | 120.2 | C55—C45—H45 | 119.5 |
C42—C32—C22 | 121.2 (6) | C45—C55—C65 | 120.2 (6) |
C42—C32—H32 | 119.4 | C45—C55—H55 | 119.9 |
C22—C32—H32 | 119.4 | C65—C55—H55 | 119.9 |
C52—C42—C32 | 119.4 (6) | C55—C65—C15 | 117.2 (6) |
C52—C42—H42 | 120.3 | C55—C65—H65 | 121.4 |
C32—C42—H42 | 120.3 | C15—C65—H65 | 121.4 |
Cg1 and Cg2 are the centroids of the C12/C62/C63/C13/C4 and C14/C24/C34/C44/C54/C64 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···Cg1 | 0.93 | 2.71 | 3.470 (10) | 140 |
C22—H22···Cg2 | 0.93 | 2.83 | 3.665 (9) | 149 |
[Os3H(C13H7)(CO)9] | F(000) = 1760 |
Mr = 986.88 | Dx = 2.900 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 9.3325 (13) Å | θ = 5–12.5° |
b = 13.960 (2) Å | µ = 16.87 mm−1 |
c = 17.865 (3) Å | T = 295 K |
β = 103.771 (13)° | Needle, orange |
V = 2260.6 (6) Å3 | 0.12 × 0.08 × 0.06 mm |
Z = 4 |
Siemens R3m diffractometer | 2892 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.051 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
ω/2θ scans | h = −1→11 |
Absorption correction: ψ scan (XEMP in SHELXTL-NT; Sheldrick, 2008) | k = −1→16 |
Tmin = 0.22, Tmax = 0.38 | l = −21→20 |
4675 measured reflections | 2 standard reflections every 98 reflections |
3975 independent reflections | intensity decay: 1% |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0364P)2] where P = (Fo2 + 2Fc2)/3 |
3975 reflections | (Δ/σ)max = 0.001 |
311 parameters | Δρmax = 1.17 e Å−3 |
143 restraints | Δρmin = −1.30 e Å−3 |
Experimental. Spectroscopic data for (II): IR data [cyclohexane, n(CO), cm-1]: 2095m, 2067ms, 2050ms, 2032mw, 2016w, 2001w, 1990mw; 1H NMR (acetone-d6, δ, p.p.m.): 8.38dd (1H), 8,28td (1H), 8.06dd (1H), 8.01m (1H), 7.65dd (1H), 7.62dt (1H), 7.53dt (1H), -18.3s (Os-H). |
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. |
x | y | z | Uiso*/Ueq | ||
Os1 | 0.64687 (6) | 0.80258 (4) | 0.05241 (3) | 0.03423 (16) | |
Os2 | 0.69732 (6) | 0.62514 (4) | 0.14762 (3) | 0.02987 (15) | |
H12 | 0.625 (13) | 0.668 (5) | 0.046 (5) | 0.036* | |
Os3 | 0.91348 (6) | 0.77009 (4) | 0.16136 (3) | 0.03143 (15) | |
C1 | 0.4904 (18) | 0.8402 (11) | 0.1037 (9) | 0.050 (3) | |
O1 | 0.4048 (17) | 0.8640 (10) | 0.1326 (8) | 0.093 (5) | |
C2 | 0.6806 (17) | 0.9340 (10) | 0.0394 (8) | 0.046 (3) | |
O2 | 0.7042 (15) | 1.0131 (8) | 0.0302 (8) | 0.079 (4) | |
C3 | 0.5173 (17) | 0.7918 (10) | −0.0467 (8) | 0.043 (3) | |
O3 | 0.4422 (15) | 0.7833 (8) | −0.1060 (6) | 0.072 (4) | |
C4 | 0.5293 (18) | 0.6580 (11) | 0.1903 (10) | 0.051 (4) | |
O4 | 0.4360 (17) | 0.6751 (10) | 0.2168 (10) | 0.106 (5) | |
C5 | 0.7890 (16) | 0.5708 (11) | 0.2447 (9) | 0.045 (3) | |
O5 | 0.8381 (14) | 0.5395 (7) | 0.3042 (6) | 0.065 (3) | |
C6 | 0.6158 (16) | 0.5086 (10) | 0.1035 (8) | 0.035 (3) | |
O6 | 0.5766 (11) | 0.4365 (7) | 0.0750 (6) | 0.048 (3) | |
C7 | 1.005 (2) | 0.8914 (11) | 0.1556 (10) | 0.064 (4) | |
O7 | 1.0633 (17) | 0.9620 (9) | 0.1490 (9) | 0.106 (5) | |
C8 | 1.0765 (17) | 0.7181 (10) | 0.2352 (8) | 0.041 (3) | |
O8 | 1.1673 (12) | 0.6855 (8) | 0.2820 (6) | 0.063 (3) | |
C9 | 0.8105 (18) | 0.8140 (10) | 0.2324 (8) | 0.047 (3) | |
O9 | 0.7459 (12) | 0.8417 (8) | 0.2752 (6) | 0.060 (3) | |
C10 | 0.8903 (14) | 0.6179 (9) | 0.1107 (7) | 0.029 (2) | |
C11 | 0.9271 (14) | 0.6832 (9) | 0.0526 (7) | 0.028 (2) | |
C21 | 0.8445 (16) | 0.7666 (10) | 0.0228 (8) | 0.036 (2) | |
C31 | 0.9179 (19) | 0.8207 (12) | −0.0267 (8) | 0.053 (4) | |
H31 | 0.8774 | 0.8789 | −0.0465 | 0.064* | |
C41 | 1.039 (2) | 0.7910 (11) | −0.0447 (9) | 0.055 (4) | |
H41 | 1.0759 | 0.8284 | −0.0790 | 0.067* | |
C51 | 1.1177 (18) | 0.7082 (11) | −0.0168 (9) | 0.050 (4) | |
H51 | 1.2024 | 0.6905 | −0.0323 | 0.061* | |
C61 | 1.0639 (14) | 0.6542 (10) | 0.0344 (7) | 0.032 (3) | |
C12 | 1.0087 (15) | 0.5455 (9) | 0.1233 (7) | 0.031 (3) | |
C22 | 1.0293 (17) | 0.4653 (10) | 0.1685 (8) | 0.044 (4) | |
H22 | 0.9635 | 0.4506 | 0.1985 | 0.053* | |
C32 | 1.1501 (16) | 0.4054 (11) | 0.1692 (9) | 0.050 (4) | |
H32 | 1.1636 | 0.3510 | 0.2002 | 0.059* | |
C42 | 1.2497 (16) | 0.4249 (10) | 0.1251 (9) | 0.045 (3) | |
H42 | 1.3303 | 0.3850 | 0.1270 | 0.054* | |
C52 | 1.2276 (17) | 0.5047 (10) | 0.0781 (9) | 0.046 (4) | |
H52 | 1.2912 | 0.5171 | 0.0462 | 0.055* | |
C62 | 1.1110 (15) | 0.5668 (10) | 0.0780 (8) | 0.037 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Os1 | 0.0419 (3) | 0.0272 (3) | 0.0301 (3) | 0.0056 (3) | 0.0017 (2) | 0.0003 (2) |
Os2 | 0.0345 (3) | 0.0259 (3) | 0.0306 (3) | −0.0005 (2) | 0.0105 (2) | −0.0005 (2) |
Os3 | 0.0391 (3) | 0.0244 (3) | 0.0280 (3) | −0.0026 (2) | 0.0026 (2) | −0.0023 (2) |
C1 | 0.054 (7) | 0.049 (8) | 0.042 (8) | 0.018 (7) | 0.003 (6) | −0.002 (7) |
O1 | 0.115 (12) | 0.097 (11) | 0.081 (10) | 0.051 (9) | 0.050 (9) | −0.002 (8) |
C2 | 0.060 (10) | 0.033 (5) | 0.034 (8) | 0.008 (5) | −0.014 (6) | 0.002 (5) |
O2 | 0.097 (10) | 0.025 (5) | 0.105 (11) | 0.009 (6) | 0.003 (8) | 0.010 (6) |
C3 | 0.058 (8) | 0.027 (7) | 0.035 (6) | 0.016 (7) | −0.007 (5) | 0.000 (5) |
O3 | 0.102 (10) | 0.068 (8) | 0.031 (6) | −0.010 (7) | −0.013 (6) | 0.003 (6) |
C4 | 0.052 (8) | 0.046 (9) | 0.062 (10) | 0.003 (6) | 0.030 (7) | 0.000 (7) |
O4 | 0.105 (12) | 0.088 (11) | 0.156 (15) | 0.013 (9) | 0.093 (11) | −0.014 (10) |
C5 | 0.043 (8) | 0.049 (9) | 0.042 (6) | −0.016 (6) | 0.007 (6) | 0.008 (6) |
O5 | 0.110 (10) | 0.041 (6) | 0.035 (5) | −0.011 (7) | 0.001 (6) | 0.007 (5) |
C6 | 0.041 (8) | 0.033 (6) | 0.039 (7) | −0.008 (5) | 0.025 (6) | −0.001 (5) |
O6 | 0.058 (7) | 0.036 (5) | 0.048 (6) | −0.012 (5) | 0.011 (5) | 0.000 (5) |
C7 | 0.090 (11) | 0.031 (6) | 0.059 (10) | −0.023 (7) | −0.008 (8) | −0.005 (6) |
O7 | 0.122 (13) | 0.056 (8) | 0.120 (13) | −0.053 (8) | −0.007 (10) | 0.013 (8) |
C8 | 0.043 (6) | 0.036 (8) | 0.038 (7) | −0.006 (5) | −0.003 (5) | −0.004 (5) |
O8 | 0.050 (7) | 0.075 (8) | 0.054 (7) | 0.014 (6) | −0.006 (5) | −0.003 (6) |
C9 | 0.070 (10) | 0.039 (7) | 0.031 (6) | 0.019 (7) | 0.005 (6) | −0.006 (6) |
O9 | 0.061 (7) | 0.078 (8) | 0.038 (6) | 0.030 (6) | 0.004 (5) | −0.016 (6) |
C10 | 0.032 (5) | 0.020 (4) | 0.034 (6) | −0.003 (4) | 0.006 (5) | −0.002 (3) |
C11 | 0.029 (6) | 0.027 (6) | 0.030 (5) | −0.005 (4) | 0.010 (5) | −0.006 (4) |
C21 | 0.048 (6) | 0.033 (6) | 0.028 (4) | 0.002 (5) | 0.010 (5) | 0.005 (4) |
C31 | 0.073 (10) | 0.052 (9) | 0.038 (7) | −0.001 (7) | 0.020 (8) | 0.013 (7) |
C41 | 0.086 (12) | 0.042 (9) | 0.049 (10) | −0.016 (7) | 0.035 (9) | 0.006 (7) |
C51 | 0.067 (10) | 0.046 (9) | 0.048 (9) | −0.007 (7) | 0.031 (8) | −0.003 (6) |
C61 | 0.028 (6) | 0.039 (7) | 0.029 (7) | −0.006 (5) | 0.005 (5) | −0.009 (5) |
C12 | 0.036 (7) | 0.024 (5) | 0.033 (7) | −0.002 (5) | 0.005 (5) | −0.012 (4) |
C22 | 0.051 (9) | 0.041 (8) | 0.045 (9) | 0.013 (6) | 0.017 (7) | 0.005 (6) |
C32 | 0.039 (8) | 0.038 (8) | 0.069 (11) | 0.002 (6) | 0.007 (7) | 0.006 (7) |
C42 | 0.037 (8) | 0.038 (8) | 0.059 (10) | 0.006 (6) | 0.009 (7) | −0.007 (6) |
C52 | 0.044 (9) | 0.047 (8) | 0.051 (9) | 0.003 (6) | 0.023 (7) | −0.002 (6) |
C62 | 0.044 (8) | 0.033 (7) | 0.034 (8) | 0.004 (5) | 0.011 (6) | −0.008 (5) |
Os1—C2 | 1.885 (15) | C7—O7 | 1.144 (18) |
Os1—C3 | 1.898 (14) | C8—O8 | 1.135 (16) |
Os1—C1 | 1.971 (17) | C9—O9 | 1.148 (16) |
Os1—C21 | 2.097 (14) | C10—C11 | 1.482 (17) |
Os1—H12 | 1.89 (7) | C10—C12 | 1.475 (18) |
Os2—C6 | 1.886 (14) | C11—C21 | 1.427 (18) |
Os2—C5 | 1.900 (15) | C11—C61 | 1.448 (18) |
Os2—C4 | 1.954 (16) | C21—C31 | 1.454 (19) |
Os2—C10 | 2.062 (13) | C31—C41 | 1.32 (2) |
Os2—H12 | 1.88 (7) | C31—H31 | 0.9300 |
Os3—C9 | 1.868 (15) | C41—C51 | 1.40 (2) |
Os3—C8 | 1.904 (15) | C41—H41 | 0.9300 |
Os3—C7 | 1.912 (16) | C51—C61 | 1.369 (19) |
Os3—C10 | 2.299 (12) | C51—H51 | 0.9300 |
Os3—C11 | 2.319 (12) | C61—C62 | 1.458 (19) |
Os3—C21 | 2.405 (13) | C12—C22 | 1.367 (19) |
Os1—Os2 | 2.9782 (8) | C12—C62 | 1.422 (19) |
Os1—Os3 | 2.8070 (9) | C22—C32 | 1.402 (19) |
Os2—Os3 | 2.8264 (8) | C22—H22 | 0.9300 |
C1—O1 | 1.101 (18) | C32—C42 | 1.38 (2) |
C2—O2 | 1.146 (17) | C32—H32 | 0.9300 |
C3—O3 | 1.129 (16) | C42—C52 | 1.38 (2) |
C4—O4 | 1.112 (17) | C42—H42 | 0.9300 |
C5—O5 | 1.139 (16) | C52—C62 | 1.391 (19) |
C6—O6 | 1.149 (15) | C52—H52 | 0.9300 |
C2—Os1—C3 | 92.9 (6) | C8—Os3—Os2 | 102.9 (4) |
C2—Os1—C1 | 87.8 (7) | C7—Os3—Os2 | 161.6 (6) |
C3—Os1—C1 | 94.4 (6) | C10—Os3—Os2 | 46.0 (3) |
C2—Os1—C21 | 91.1 (6) | C11—Os3—Os2 | 74.5 (3) |
C3—Os1—C21 | 98.6 (6) | C21—Os3—Os2 | 83.4 (3) |
C1—Os1—C21 | 167.0 (6) | Os1—Os3—Os2 | 63.83 (2) |
C2—Os1—Os3 | 95.5 (4) | O1—C1—Os1 | 177.7 (17) |
C3—Os1—Os3 | 153.8 (4) | O2—C2—Os1 | 177.9 (16) |
C1—Os1—Os3 | 110.7 (4) | O3—C3—Os1 | 178.2 (14) |
C21—Os1—Os3 | 56.5 (4) | O4—C4—Os2 | 177.6 (17) |
C2—Os1—Os2 | 150.6 (4) | O5—C5—Os2 | 176.7 (15) |
C3—Os1—Os2 | 116.5 (4) | O6—C6—Os2 | 174.5 (12) |
C1—Os1—Os2 | 89.4 (5) | O7—C7—Os3 | 176.3 (19) |
C21—Os1—Os2 | 85.2 (4) | O8—C8—Os3 | 175.5 (14) |
Os3—Os1—Os2 | 58.402 (19) | O9—C9—Os3 | 179.0 (13) |
C2—Os1—H12 | 168 (3) | C11—C10—C12 | 103.8 (11) |
C3—Os1—H12 | 80 (3) | C11—C10—Os2 | 124.0 (9) |
C1—Os1—H12 | 102 (3) | C12—C10—Os2 | 131.6 (9) |
C21—Os1—H12 | 80 (4) | C11—C10—Os3 | 72.0 (7) |
Os3—Os1—H12 | 87 (3) | C12—C10—Os3 | 125.2 (9) |
Os2—Os1—H12 | 38 (3) | Os2—C10—Os3 | 80.6 (4) |
C6—Os2—C5 | 94.9 (6) | C21—C11—C61 | 124.8 (12) |
C6—Os2—C4 | 94.8 (6) | C21—C11—C10 | 124.6 (12) |
C5—Os2—C4 | 88.1 (7) | C61—C11—C10 | 110.5 (11) |
C6—Os2—C10 | 96.9 (5) | C21—C11—Os3 | 75.7 (7) |
C5—Os2—C10 | 92.0 (6) | C61—C11—Os3 | 124.2 (9) |
C4—Os2—C10 | 168.2 (6) | C10—C11—Os3 | 70.6 (7) |
C6—Os2—Os3 | 149.5 (4) | C11—C21—C31 | 111.1 (13) |
C5—Os2—Os3 | 92.9 (4) | C11—C21—Os1 | 122.1 (9) |
C4—Os2—Os3 | 114.9 (5) | C31—C21—Os1 | 126.8 (11) |
C10—Os2—Os3 | 53.4 (3) | C11—C21—Os3 | 69.2 (7) |
C6—Os2—Os1 | 119.0 (4) | C31—C21—Os3 | 124.5 (10) |
C5—Os2—Os1 | 146.0 (4) | Os1—C21—Os3 | 76.8 (4) |
C4—Os2—Os1 | 89.7 (5) | C41—C31—C21 | 122.9 (15) |
C10—Os2—Os1 | 83.6 (3) | C41—C31—H31 | 118.6 |
Os3—Os2—Os1 | 57.77 (2) | C21—C31—H31 | 118.6 |
C6—Os2—H12 | 82 (3) | C31—C41—C51 | 125.7 (15) |
C5—Os2—H12 | 172 (3) | C31—C41—H41 | 117.2 |
C4—Os2—H12 | 100 (3) | C51—C41—H41 | 117.2 |
C10—Os2—H12 | 81 (4) | C61—C51—C41 | 116.7 (15) |
Os3—Os2—H12 | 86 (3) | C61—C51—H51 | 121.7 |
Os1—Os2—H12 | 38 (3) | C41—C51—H51 | 121.7 |
C9—Os3—C8 | 96.3 (6) | C51—C61—C11 | 118.7 (13) |
C9—Os3—C7 | 93.2 (8) | C51—C61—C62 | 134.8 (14) |
C8—Os3—C7 | 94.7 (7) | C11—C61—C62 | 106.4 (11) |
C9—Os3—C10 | 123.7 (6) | C22—C12—C62 | 119.2 (13) |
C8—Os3—C10 | 84.6 (5) | C22—C12—C10 | 130.3 (13) |
C7—Os3—C10 | 143.0 (7) | C62—C12—C10 | 110.5 (12) |
C9—Os3—C11 | 151.7 (6) | C12—C22—C32 | 119.6 (14) |
C8—Os3—C11 | 100.8 (5) | C12—C22—H22 | 120.2 |
C7—Os3—C11 | 107.7 (6) | C32—C22—H22 | 120.2 |
C10—Os3—C11 | 37.4 (4) | C42—C32—C22 | 121.7 (14) |
C9—Os3—C21 | 130.6 (6) | C42—C32—H32 | 119.1 |
C8—Os3—C21 | 132.8 (6) | C22—C32—H32 | 119.1 |
C7—Os3—C21 | 88.6 (6) | C52—C42—C32 | 118.9 (14) |
C10—Os3—C21 | 66.4 (5) | C52—C42—H42 | 120.5 |
C11—Os3—C21 | 35.1 (4) | C32—C42—H42 | 120.5 |
C9—Os3—Os1 | 84.5 (5) | C42—C52—C62 | 120.5 (14) |
C8—Os3—Os1 | 166.4 (4) | C42—C52—H52 | 119.8 |
C7—Os3—Os1 | 98.8 (5) | C62—C52—H52 | 119.8 |
C10—Os3—Os1 | 83.8 (3) | C52—C62—C12 | 120.0 (13) |
C11—Os3—Os1 | 73.7 (3) | C52—C62—C61 | 131.2 (13) |
C21—Os3—Os1 | 46.7 (3) | C12—C62—C61 | 108.7 (12) |
C9—Os3—Os2 | 79.7 (5) |
Group 1···Group 2 | CCD (Å) | IPD (Å) | IPA (°) | SA (°) |
Cg1···Cg3i | 3.808 (8) | 3.526 (6) | 2.3 (7) | 22.15 (16) |
Cg2···Cg3i | 3.850 (8) | 3.520 (6) | 2.6 (7) | 23.9 (2) |
Symmetry code: (i) -x+2, -y+1, -z. Cg1, Cg2 and Cg3 are the centroids of the C10/C11/C61/C62/C12, C11/C21/C31/C41/C51/C61 and C12/C22/C32/C42/C52/C62 rings, respectively. CCD is the centroid-to-centroid distance, IPD is the mean interplanar distance, IPA is the interplanar angle and SA is the mean slippage angle. For details, see Janiak (2000). |