Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803001673/bt6233sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803001673/bt62333sup2.hkl |
CCDC reference: 204665
Key indicators
- Single-crystal X-ray study
- T = 178 K
- Mean (C-C) = 0.004 Å
- R factor = 0.028
- wR factor = 0.071
- Data-to-parameter ratio = 14.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Hydrocarbon (1) was monometalated using methyl lithium in THF at 233 K. The mixture was stirred for 30 min at 273 K and the pentamethylcyclopentadienyl ruthenium chloride tetramer was then added. Reaction was complete after 1 h at room temperature. The solvent was removed in vacuo and the remaining solid recrystallized from hexane; the monoruthenium complex, (2), was isolated in 92% yield as yellow needles and characterized by spectroscopic and analytical data. Repetition of the reaction sequence furnished the bis-ruthenium complex, (3), as yellow prisms in 91% yield. Spectroscopic data are again in full accord with the structural assignment. For full details, see Hartig (1991).
Methyl H atoms were identified in difference syntheses, idealized and then refined using rigid methyl groups allowed to rotate but not tip. Other H atoms were included using a riding model, with fixed C—H bond lengths (aromatic C—H = 0.95 Å, and methyl and methylene C—H = 0.99 Å); Uiso(H) values were fixed at 1.2Ueq of the parent atom.
Data collection: P3 (Nicolet, 1987); cell refinement: P3; data reduction: XDISK (Nicolet, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
[Ru2(C10H15)2(C22H18)] | F(000) = 1552 |
Mr = 754.94 | Dx = 1.473 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.647 (2) Å | Cell parameters from 50 reflections |
b = 13.604 (4) Å | θ = 10–11.5° |
c = 28.959 (8) Å | µ = 0.92 mm−1 |
β = 92.41 (2)° | T = 178 K |
V = 3403.5 (16) Å3 | Prism, yellow |
Z = 4 | 0.7 × 0.4 × 0.15 mm |
Nicolet R3 diffractometer | 5079 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.0°, θmin = 3.1° |
ω–2θ scans | h = 0→10 |
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983) | k = −16→10 |
Tmin = 0.66, Tmax = 0.84 | l = −34→34 |
11146 measured reflections | 3 standard reflections every 147 reflections |
5984 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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.071 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0398P)2 + 1.6478P] where P = (Fo2 + 2Fc2)/3 |
5984 reflections | (Δ/σ)max = 0.002 |
407 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.61 e Å−3 |
[Ru2(C10H15)2(C22H18)] | V = 3403.5 (16) Å3 |
Mr = 754.94 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.647 (2) Å | µ = 0.92 mm−1 |
b = 13.604 (4) Å | T = 178 K |
c = 28.959 (8) Å | 0.7 × 0.4 × 0.15 mm |
β = 92.41 (2)° |
Nicolet R3 diffractometer | 5079 reflections with I > 2σ(I) |
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983) | Rint = 0.020 |
Tmin = 0.66, Tmax = 0.84 | 3 standard reflections every 147 reflections |
11146 measured reflections | intensity decay: none |
5984 independent reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.071 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.42 e Å−3 |
5984 reflections | Δρmin = −0.61 e Å−3 |
407 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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) − 0.2007 (0.0124) x + 1.9710 (0.0193) y + 28.6485 (0.0117) z = 3.1397 (0.0043) * 0.0024 (0.0018) C19 * −0.0041 (0.0018) C20 * 0.0042 (0.0017) C21 * −0.0027 (0.0018) C22 * 0.0003 (0.0018) C23 1.7952 (0.0014) Ru1 Rms deviation of fitted atoms = 0.0031 − 0.0177 (0.0118) x + 1.4424 (0.0176) y + 28.7727 (0.0109) z = 6.7179 (0.0045) Angle to previous plane (with approximate e.s.d.) = 2.55 (0.05) * 0.0089 (0.0016) C3A * −0.0115 (0.0016) C4 * 0.0097 (0.0017) C5 * −0.0041 (0.0017) C6 * −0.0029 (0.0016) C6A −1.8353 (0.0013) Ru1 Rms deviation of fitted atoms = 0.0082 − 0.3566 (0.0121) x − 1.0905 (0.0185) y + 28.8658 (0.0106) z = 9.3512 (0.0071) Angle to previous plane (with approximate e.s.d.) = 10.92 (0.04) * −0.0018 (0.0017) C12A * 0.0070 (0.0018) C13 * −0.0096 (0.0018) C14 * 0.0083 (0.0018) C15 * −0.0040 (0.0017) C15A 1.8416 (0.0014) Ru2 Rms deviation of fitted atoms = 0.0068 − 0.2139 (0.0124) x − 1.6263 (0.0186) y + 28.7471 (0.0111) z = 12.8521 (0.0082) Angle to previous plane (with approximate e.s.d.) = 2.45 (0.05) * −0.0033 (0.0017) C19' * 0.0019 (0.0017) C20' * 0.0002 (0.0018) C21' * −0.0022 (0.0018) C22' * 0.0034 (0.0017) C23' −1.7978 (0.0014) Ru2 Rms deviation of fitted atoms = 0.0025 − 0.1351 (0.0147) x + 0.4123 (0.0169) y + 28.9356 (0.0102) z = 6.5725 (0.0030) Angle to previous plane (with approximate e.s.d.) = 8.62 (0.04) * −0.0086 (0.0013) C3A * 0.0086 (0.0013) C6A * −0.0088 (0.0013) C8 * 0.0087 (0.0013) C9 0.1512 (0.0039) C3 0.1421 (0.0040) C7 Rms deviation of fitted atoms = 0.0087 − 0.1316 (0.0152) x − 0.0392 (0.0175) y + 28.9484 (0.0102) z = 9.6061 (0.0041) Angle to previous plane (with approximate e.s.d.) = 1.90 (0.02) * −0.0044 (0.0013) C12A * 0.0044 (0.0013) C15A * −0.0045 (0.0014) C17 * 0.0045 (0.0014) C18 − 0.1487 (0.0042) C12 − 0.1506 (0.0040) C16 Rms deviation of fitted atoms = 0.0044 |
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 | 0.21577 (3) | 0.211206 (16) | 0.159240 (7) | 0.01877 (7) | |
Ru2 | 0.24087 (3) | 0.234186 (17) | 0.399575 (7) | 0.02075 (7) | |
C1 | −0.1676 (3) | 0.1775 (3) | 0.30503 (10) | 0.0322 (7) | |
H1A | −0.1774 | 0.2478 | 0.3133 | 0.039* | |
H1B | −0.2554 | 0.1419 | 0.3182 | 0.039* | |
C2 | −0.1789 (3) | 0.1672 (2) | 0.25058 (10) | 0.0261 (6) | |
H2A | −0.2693 | 0.1256 | 0.2418 | 0.031* | |
H2B | −0.1971 | 0.2331 | 0.2369 | 0.031* | |
C3 | −0.0370 (3) | 0.1233 (2) | 0.23044 (9) | 0.0202 (6) | |
C3A | 0.0977 (3) | 0.1825 (2) | 0.22470 (8) | 0.0172 (5) | |
C4 | 0.1177 (3) | 0.2861 (2) | 0.21881 (9) | 0.0205 (6) | |
H4 | 0.0372 | 0.3334 | 0.2156 | 0.025* | |
C5 | 0.2790 (3) | 0.3059 (2) | 0.21866 (9) | 0.0256 (7) | |
H5 | 0.3246 | 0.3691 | 0.2162 | 0.031* | |
C6 | 0.3611 (3) | 0.2155 (2) | 0.22276 (9) | 0.0241 (6) | |
H6 | 0.4704 | 0.2079 | 0.2229 | 0.029* | |
C6A | 0.2501 (3) | 0.1373 (2) | 0.22665 (9) | 0.0202 (6) | |
C7 | 0.2647 (3) | 0.0334 (2) | 0.23281 (9) | 0.0234 (6) | |
C8 | 0.1322 (4) | −0.0204 (2) | 0.22775 (9) | 0.0252 (6) | |
H8 | 0.1398 | −0.0897 | 0.2246 | 0.030* | |
C9 | −0.0179 (3) | 0.0238 (2) | 0.22702 (9) | 0.0235 (6) | |
H9 | −0.1068 | −0.0171 | 0.2241 | 0.028* | |
C10 | 0.4115 (4) | −0.0097 (2) | 0.25436 (11) | 0.0318 (7) | |
H10A | 0.5014 | 0.0199 | 0.2395 | 0.038* | |
H10B | 0.4130 | −0.0812 | 0.2482 | 0.038* | |
C11 | 0.4287 (4) | 0.0076 (3) | 0.30785 (12) | 0.0424 (9) | |
H11A | 0.4519 | −0.0560 | 0.3233 | 0.051* | |
H11B | 0.5177 | 0.0520 | 0.3145 | 0.051* | |
C12 | 0.2859 (4) | 0.0516 (2) | 0.32807 (10) | 0.0279 (7) | |
C12A | 0.2690 (3) | 0.1563 (2) | 0.33312 (9) | 0.0240 (6) | |
C13 | 0.3779 (4) | 0.2356 (3) | 0.33777 (10) | 0.0311 (7) | |
H13 | 0.4874 | 0.2291 | 0.3394 | 0.037* | |
C14 | 0.2947 (4) | 0.3256 (3) | 0.33956 (10) | 0.0339 (7) | |
H14 | 0.3392 | 0.3894 | 0.3418 | 0.041* | |
C15 | 0.1340 (4) | 0.3041 (2) | 0.33739 (9) | 0.0281 (7) | |
H15 | 0.0527 | 0.3508 | 0.3387 | 0.034* | |
C15A | 0.1153 (3) | 0.1995 (2) | 0.33278 (9) | 0.0217 (6) | |
C16 | −0.0177 (3) | 0.1380 (2) | 0.32674 (9) | 0.0238 (6) | |
C17 | 0.0052 (4) | 0.0390 (2) | 0.33176 (9) | 0.0275 (7) | |
H17 | −0.0820 | −0.0027 | 0.3347 | 0.033* | |
C18 | 0.1557 (4) | −0.0032 (2) | 0.33269 (10) | 0.0297 (7) | |
H18 | 0.1658 | −0.0723 | 0.3367 | 0.036* | |
C19 | 0.2579 (4) | 0.2760 (2) | 0.09249 (10) | 0.0310 (7) | |
C20 | 0.1001 (4) | 0.2469 (2) | 0.09317 (9) | 0.0259 (6) | |
C21 | 0.0946 (3) | 0.1428 (2) | 0.10058 (9) | 0.0239 (6) | |
C22 | 0.2515 (3) | 0.1071 (2) | 0.10389 (10) | 0.0276 (7) | |
C23 | 0.3524 (4) | 0.1892 (3) | 0.09906 (10) | 0.0322 (7) | |
C24 | 0.3159 (5) | 0.3778 (3) | 0.08325 (11) | 0.0502 (10) | |
H24A | 0.4215 | 0.3849 | 0.0965 | 0.060* | |
H24B | 0.2483 | 0.4260 | 0.0974 | 0.060* | |
H24C | 0.3158 | 0.3890 | 0.0498 | 0.060* | |
C25 | −0.0383 (4) | 0.3115 (3) | 0.08402 (11) | 0.0412 (8) | |
H25A | −0.0681 | 0.3097 | 0.0510 | 0.049* | |
H25B | −0.0127 | 0.3791 | 0.0931 | 0.049* | |
H25C | −0.1245 | 0.2879 | 0.1019 | 0.049* | |
C26 | −0.0495 (4) | 0.0825 (2) | 0.10334 (11) | 0.0339 (7) | |
H26A | −0.1293 | 0.1210 | 0.1181 | 0.041* | |
H26B | −0.0269 | 0.0231 | 0.1216 | 0.041* | |
H26C | −0.0865 | 0.0639 | 0.0721 | 0.041* | |
C27 | 0.2979 (4) | 0.0014 (3) | 0.10996 (12) | 0.0426 (9) | |
H27A | 0.2965 | −0.0310 | 0.0797 | 0.051* | |
H27B | 0.2252 | −0.0317 | 0.1298 | 0.051* | |
H27C | 0.4025 | −0.0021 | 0.1243 | 0.051* | |
C28 | 0.5257 (4) | 0.1859 (4) | 0.09858 (13) | 0.0575 (11) | |
H28A | 0.5642 | 0.1306 | 0.1174 | 0.069* | |
H28B | 0.5685 | 0.2475 | 0.1112 | 0.069* | |
H28C | 0.5576 | 0.1776 | 0.0667 | 0.069* | |
C19' | 0.1257 (3) | 0.1701 (2) | 0.45752 (9) | 0.0234 (6) | |
C20' | 0.1327 (4) | 0.2747 (2) | 0.46367 (10) | 0.0261 (7) | |
C21' | 0.2919 (4) | 0.3033 (2) | 0.46641 (9) | 0.0271 (7) | |
C22' | 0.3850 (4) | 0.2157 (2) | 0.46206 (10) | 0.0274 (7) | |
C23' | 0.2813 (4) | 0.1335 (2) | 0.45684 (9) | 0.0264 (6) | |
C24' | −0.0181 (4) | 0.1090 (2) | 0.45310 (11) | 0.0336 (7) | |
H24D | −0.0388 | 0.0795 | 0.4831 | 0.040* | |
H24E | −0.0041 | 0.0568 | 0.4303 | 0.040* | |
H24F | −0.1057 | 0.1506 | 0.4430 | 0.040* | |
C25' | −0.0034 (4) | 0.3412 (2) | 0.46980 (11) | 0.0369 (8) | |
H25D | −0.0294 | 0.3419 | 0.5024 | 0.044* | |
H25E | −0.0923 | 0.3171 | 0.4510 | 0.044* | |
H25F | 0.0227 | 0.4079 | 0.4600 | 0.044* | |
C26' | 0.3520 (4) | 0.4051 (2) | 0.47592 (11) | 0.0378 (8) | |
H26D | 0.2831 | 0.4532 | 0.4605 | 0.045* | |
H26E | 0.4562 | 0.4115 | 0.4641 | 0.045* | |
H26F | 0.3561 | 0.4172 | 0.5093 | 0.045* | |
C27' | 0.5576 (4) | 0.2111 (3) | 0.46530 (13) | 0.0448 (9) | |
H27D | 0.5925 | 0.1999 | 0.4975 | 0.054* | |
H27E | 0.6003 | 0.2733 | 0.4545 | 0.054* | |
H27F | 0.5932 | 0.1571 | 0.4460 | 0.054* | |
C28' | 0.3259 (4) | 0.0278 (2) | 0.45288 (11) | 0.0354 (8) | |
H28D | 0.4332 | 0.0232 | 0.4434 | 0.042* | |
H28E | 0.2573 | −0.0045 | 0.4298 | 0.042* | |
H28F | 0.3166 | −0.0046 | 0.4829 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.01803 (12) | 0.01958 (12) | 0.01875 (12) | −0.00265 (9) | 0.00121 (9) | 0.00049 (8) |
Ru2 | 0.02073 (13) | 0.02264 (13) | 0.01883 (12) | −0.00141 (9) | 0.00025 (9) | 0.00011 (9) |
C1 | 0.0190 (15) | 0.044 (2) | 0.0335 (16) | 0.0009 (14) | 0.0049 (13) | −0.0052 (14) |
C2 | 0.0158 (14) | 0.0326 (17) | 0.0300 (15) | −0.0002 (12) | 0.0008 (12) | 0.0019 (13) |
C3 | 0.0169 (14) | 0.0253 (15) | 0.0181 (13) | −0.0024 (11) | −0.0021 (11) | 0.0019 (11) |
C3A | 0.0163 (13) | 0.0197 (14) | 0.0156 (12) | −0.0002 (11) | −0.0009 (10) | 0.0006 (10) |
C4 | 0.0252 (15) | 0.0177 (14) | 0.0186 (13) | 0.0001 (12) | 0.0010 (11) | −0.0001 (10) |
C5 | 0.0278 (16) | 0.0256 (16) | 0.0232 (14) | −0.0121 (13) | 0.0002 (12) | −0.0004 (12) |
C6 | 0.0173 (14) | 0.0316 (17) | 0.0232 (14) | −0.0043 (12) | −0.0016 (11) | 0.0023 (12) |
C6A | 0.0157 (14) | 0.0282 (16) | 0.0166 (13) | −0.0016 (12) | −0.0002 (11) | 0.0015 (11) |
C7 | 0.0260 (16) | 0.0250 (15) | 0.0194 (13) | 0.0064 (12) | 0.0033 (12) | 0.0021 (11) |
C8 | 0.0375 (18) | 0.0179 (14) | 0.0205 (14) | 0.0005 (13) | 0.0045 (12) | 0.0000 (11) |
C9 | 0.0239 (15) | 0.0235 (15) | 0.0227 (14) | −0.0082 (12) | −0.0027 (12) | 0.0008 (11) |
C10 | 0.0270 (17) | 0.0339 (18) | 0.0349 (17) | 0.0116 (14) | 0.0057 (14) | 0.0045 (13) |
C11 | 0.0325 (19) | 0.055 (2) | 0.0390 (19) | 0.0213 (17) | −0.0116 (15) | −0.0152 (16) |
C12 | 0.0307 (17) | 0.0326 (17) | 0.0201 (14) | 0.0115 (14) | −0.0039 (12) | −0.0033 (12) |
C12A | 0.0209 (15) | 0.0360 (17) | 0.0151 (13) | 0.0007 (13) | 0.0013 (11) | −0.0026 (12) |
C13 | 0.0228 (16) | 0.048 (2) | 0.0224 (14) | −0.0069 (14) | 0.0034 (12) | −0.0036 (14) |
C14 | 0.044 (2) | 0.0337 (18) | 0.0242 (15) | −0.0143 (15) | 0.0007 (14) | 0.0019 (13) |
C15 | 0.0400 (18) | 0.0249 (16) | 0.0190 (13) | 0.0010 (14) | −0.0019 (13) | 0.0020 (12) |
C15A | 0.0230 (15) | 0.0255 (15) | 0.0167 (13) | 0.0020 (12) | 0.0007 (11) | 0.0005 (11) |
C16 | 0.0227 (15) | 0.0308 (16) | 0.0182 (13) | 0.0001 (12) | 0.0047 (11) | −0.0021 (12) |
C17 | 0.0291 (17) | 0.0316 (17) | 0.0220 (14) | −0.0085 (13) | 0.0040 (12) | 0.0002 (12) |
C18 | 0.0439 (19) | 0.0238 (16) | 0.0212 (15) | 0.0039 (14) | −0.0003 (13) | 0.0005 (12) |
C19 | 0.0423 (19) | 0.0333 (17) | 0.0177 (14) | −0.0113 (15) | 0.0035 (13) | 0.0016 (12) |
C20 | 0.0373 (17) | 0.0220 (15) | 0.0183 (13) | −0.0001 (13) | −0.0020 (12) | −0.0021 (11) |
C21 | 0.0273 (16) | 0.0259 (16) | 0.0183 (13) | −0.0015 (13) | 0.0003 (12) | −0.0027 (11) |
C22 | 0.0285 (16) | 0.0319 (17) | 0.0225 (14) | 0.0046 (13) | 0.0037 (12) | −0.0055 (12) |
C23 | 0.0271 (17) | 0.047 (2) | 0.0231 (15) | −0.0052 (15) | 0.0087 (13) | −0.0031 (14) |
C24 | 0.077 (3) | 0.046 (2) | 0.0278 (17) | −0.033 (2) | 0.0046 (18) | 0.0046 (15) |
C25 | 0.054 (2) | 0.0330 (19) | 0.0359 (18) | 0.0146 (17) | −0.0123 (16) | −0.0040 (14) |
C26 | 0.0343 (18) | 0.0336 (18) | 0.0335 (17) | −0.0132 (15) | −0.0015 (14) | −0.0082 (14) |
C27 | 0.051 (2) | 0.038 (2) | 0.0391 (19) | 0.0177 (17) | 0.0055 (17) | −0.0063 (15) |
C28 | 0.029 (2) | 0.095 (3) | 0.050 (2) | −0.010 (2) | 0.0164 (17) | −0.008 (2) |
C19' | 0.0293 (16) | 0.0229 (15) | 0.0181 (13) | 0.0017 (13) | 0.0026 (12) | 0.0024 (11) |
C20' | 0.0335 (17) | 0.0244 (16) | 0.0206 (14) | 0.0042 (13) | 0.0033 (12) | 0.0031 (11) |
C21' | 0.0354 (18) | 0.0274 (16) | 0.0183 (13) | −0.0025 (14) | −0.0026 (12) | −0.0006 (12) |
C22' | 0.0284 (16) | 0.0299 (17) | 0.0234 (14) | 0.0023 (13) | −0.0056 (12) | −0.0001 (12) |
C23' | 0.0325 (17) | 0.0267 (16) | 0.0197 (14) | 0.0037 (13) | −0.0015 (12) | 0.0026 (12) |
C24' | 0.0352 (18) | 0.0320 (18) | 0.0342 (17) | −0.0059 (14) | 0.0093 (14) | 0.0029 (14) |
C25' | 0.044 (2) | 0.0310 (18) | 0.0362 (17) | 0.0116 (15) | 0.0102 (15) | 0.0046 (14) |
C26' | 0.052 (2) | 0.0306 (18) | 0.0299 (17) | −0.0077 (16) | −0.0061 (15) | −0.0034 (13) |
C27' | 0.0293 (19) | 0.058 (2) | 0.047 (2) | −0.0002 (17) | −0.0090 (16) | −0.0019 (17) |
C28' | 0.043 (2) | 0.0269 (17) | 0.0359 (17) | 0.0111 (15) | −0.0006 (15) | 0.0007 (14) |
Ru1—C23 | 2.167 (3) | C15—C15A | 1.438 (4) |
Ru1—C21 | 2.168 (3) | C15—H15 | 0.9500 |
Ru1—C19 | 2.169 (3) | C15A—C16 | 1.428 (4) |
Ru1—C22 | 2.171 (3) | C16—C17 | 1.367 (4) |
Ru1—C20 | 2.176 (3) | C17—C18 | 1.422 (4) |
Ru1—C6 | 2.185 (3) | C17—H17 | 0.9500 |
Ru1—C5 | 2.200 (3) | C18—H18 | 0.9500 |
Ru1—C4 | 2.204 (3) | C19—C20 | 1.422 (4) |
Ru1—C6A | 2.205 (3) | C19—C23 | 1.444 (5) |
Ru1—C3A | 2.225 (3) | C19—C24 | 1.500 (4) |
Ru2—C23' | 2.168 (3) | C20—C21 | 1.433 (4) |
Ru2—C22' | 2.168 (3) | C20—C25 | 1.499 (4) |
Ru2—C19' | 2.170 (3) | C21—C22 | 1.441 (4) |
Ru2—C21' | 2.180 (3) | C21—C26 | 1.497 (4) |
Ru2—C20' | 2.184 (3) | C22—C23 | 1.428 (4) |
Ru2—C13 | 2.188 (3) | C22—C27 | 1.501 (4) |
Ru2—C14 | 2.203 (3) | C23—C28 | 1.500 (4) |
Ru2—C15 | 2.205 (3) | C24—H24A | 0.9800 |
Ru2—C12A | 2.219 (3) | C24—H24B | 0.9800 |
Ru2—C15A | 2.228 (3) | C24—H24C | 0.9800 |
C1—C16 | 1.515 (4) | C25—H25A | 0.9800 |
C1—C2 | 1.582 (4) | C25—H25B | 0.9800 |
C1—H1A | 0.9900 | C25—H25C | 0.9800 |
C1—H1B | 0.9900 | C26—H26A | 0.9800 |
C2—C3 | 1.504 (4) | C26—H26B | 0.9800 |
C2—H2A | 0.9900 | C26—H26C | 0.9800 |
C2—H2B | 0.9900 | C27—H27A | 0.9800 |
C3—C9 | 1.368 (4) | C27—H27B | 0.9800 |
C3—C3A | 1.431 (4) | C27—H27C | 0.9800 |
C3A—C4 | 1.430 (4) | C28—H28A | 0.9800 |
C3A—C6A | 1.454 (4) | C28—H28B | 0.9800 |
C4—C5 | 1.421 (4) | C28—H28C | 0.9800 |
C4—H4 | 0.9500 | C19'—C20' | 1.435 (4) |
C5—C6 | 1.423 (4) | C19'—C23' | 1.436 (4) |
C5—H5 | 0.9500 | C19'—C24' | 1.497 (4) |
C6—C6A | 1.440 (4) | C20'—C21' | 1.430 (4) |
C6—H6 | 0.9500 | C20'—C25' | 1.500 (4) |
C6A—C7 | 1.430 (4) | C21'—C22' | 1.446 (4) |
C7—C8 | 1.362 (4) | C21'—C26' | 1.501 (4) |
C7—C10 | 1.509 (4) | C22'—C23' | 1.437 (4) |
C8—C9 | 1.430 (4) | C22'—C27' | 1.493 (4) |
C8—H8 | 0.9500 | C23'—C28' | 1.495 (4) |
C9—H9 | 0.9500 | C24'—H24D | 0.9800 |
C10—C11 | 1.568 (4) | C24'—H24E | 0.9800 |
C10—H10A | 0.9900 | C24'—H24F | 0.9800 |
C10—H10B | 0.9900 | C25'—H25D | 0.9800 |
C11—C12 | 1.512 (4) | C25'—H25E | 0.9800 |
C11—H11A | 0.9900 | C25'—H25F | 0.9800 |
C11—H11B | 0.9900 | C26'—H26D | 0.9800 |
C12—C18 | 1.362 (4) | C26'—H26E | 0.9800 |
C12—C12A | 1.440 (4) | C26'—H26F | 0.9800 |
C12A—C13 | 1.435 (4) | C27'—H27D | 0.9800 |
C12A—C15A | 1.453 (4) | C27'—H27E | 0.9800 |
C13—C14 | 1.422 (5) | C27'—H27F | 0.9800 |
C13—H13 | 0.9500 | C28'—H28D | 0.9800 |
C14—C15 | 1.419 (4) | C28'—H28E | 0.9800 |
C14—H14 | 0.9500 | C28'—H28F | 0.9800 |
C23—Ru1—C21 | 64.67 (11) | C13—C12A—C12 | 133.2 (3) |
C23—Ru1—C19 | 38.91 (13) | C13—C12A—C15A | 107.0 (3) |
C21—Ru1—C19 | 64.53 (11) | C12—C12A—C15A | 119.8 (3) |
C23—Ru1—C22 | 38.43 (12) | C13—C12A—Ru2 | 69.81 (16) |
C21—Ru1—C22 | 38.79 (11) | C12—C12A—Ru2 | 125.1 (2) |
C19—Ru1—C22 | 64.72 (12) | C15A—C12A—Ru2 | 71.28 (15) |
C23—Ru1—C20 | 64.51 (12) | C14—C13—C12A | 108.7 (3) |
C21—Ru1—C20 | 38.51 (11) | C14—C13—Ru2 | 71.67 (17) |
C19—Ru1—C20 | 38.21 (12) | C12A—C13—Ru2 | 72.20 (16) |
C22—Ru1—C20 | 64.58 (11) | C14—C13—H13 | 125.7 |
C23—Ru1—C6 | 111.54 (11) | C12A—C13—H13 | 125.7 |
C21—Ru1—C6 | 155.96 (11) | Ru2—C13—H13 | 122.1 |
C19—Ru1—C6 | 128.84 (11) | C15—C14—C13 | 108.5 (3) |
C22—Ru1—C6 | 122.98 (11) | C15—C14—Ru2 | 71.31 (17) |
C20—Ru1—C6 | 164.01 (11) | C13—C14—Ru2 | 70.53 (17) |
C23—Ru1—C5 | 125.74 (11) | C15—C14—H14 | 125.8 |
C21—Ru1—C5 | 163.78 (11) | C13—C14—H14 | 125.8 |
C19—Ru1—C5 | 114.41 (11) | Ru2—C14—H14 | 124.0 |
C22—Ru1—C5 | 157.10 (11) | C14—C15—C15A | 108.3 (3) |
C20—Ru1—C5 | 130.32 (11) | C14—C15—Ru2 | 71.14 (17) |
C6—Ru1—C5 | 37.87 (11) | C15A—C15—Ru2 | 71.97 (16) |
C23—Ru1—C4 | 159.12 (12) | C14—C15—H15 | 125.8 |
C21—Ru1—C4 | 128.51 (11) | C15A—C15—H15 | 125.8 |
C19—Ru1—C4 | 126.46 (12) | Ru2—C15—H15 | 122.7 |
C22—Ru1—C4 | 161.99 (11) | C16—C15A—C15 | 132.7 (3) |
C20—Ru1—C4 | 114.05 (11) | C16—C15A—C12A | 119.7 (3) |
C6—Ru1—C4 | 63.59 (11) | C15—C15A—C12A | 107.5 (3) |
C5—Ru1—C4 | 37.65 (10) | C16—C15A—Ru2 | 126.24 (19) |
C23—Ru1—C6A | 126.26 (12) | C15—C15A—Ru2 | 70.19 (16) |
C21—Ru1—C6A | 122.75 (11) | C12A—C15A—Ru2 | 70.60 (15) |
C19—Ru1—C6A | 162.34 (12) | C17—C16—C15A | 116.9 (3) |
C22—Ru1—C6A | 109.77 (11) | C17—C16—C1 | 120.7 (3) |
C20—Ru1—C6A | 156.92 (11) | C15A—C16—C1 | 120.9 (3) |
C6—Ru1—C6A | 38.30 (10) | C16—C17—C18 | 121.9 (3) |
C5—Ru1—C6A | 63.55 (11) | C16—C17—H17 | 119.1 |
C4—Ru1—C6A | 63.86 (10) | C18—C17—H17 | 119.1 |
C23—Ru1—C3A | 161.11 (12) | C12—C18—C17 | 122.5 (3) |
C21—Ru1—C3A | 111.61 (10) | C12—C18—H18 | 118.8 |
C19—Ru1—C3A | 158.54 (12) | C17—C18—H18 | 118.8 |
C22—Ru1—C3A | 126.81 (11) | C20—C19—C23 | 107.9 (3) |
C20—Ru1—C3A | 125.28 (11) | C20—C19—C24 | 126.0 (3) |
C6—Ru1—C3A | 63.62 (10) | C23—C19—C24 | 126.0 (3) |
C5—Ru1—C3A | 62.89 (10) | C20—C19—Ru1 | 71.16 (16) |
C4—Ru1—C3A | 37.68 (10) | C23—C19—Ru1 | 70.45 (16) |
C6A—Ru1—C3A | 38.31 (10) | C24—C19—Ru1 | 127.2 (2) |
C23'—Ru2—C22' | 38.72 (11) | C19—C20—C21 | 108.4 (3) |
C23'—Ru2—C19' | 38.67 (11) | C19—C20—C25 | 126.4 (3) |
C22'—Ru2—C19' | 64.81 (11) | C21—C20—C25 | 125.1 (3) |
C23'—Ru2—C21' | 64.74 (11) | C19—C20—Ru1 | 70.63 (17) |
C22'—Ru2—C21' | 38.85 (11) | C21—C20—Ru1 | 70.43 (16) |
C19'—Ru2—C21' | 64.48 (11) | C25—C20—Ru1 | 128.3 (2) |
C23'—Ru2—C20' | 64.58 (11) | C20—C21—C22 | 107.8 (3) |
C22'—Ru2—C20' | 64.64 (12) | C20—C21—C26 | 125.6 (3) |
C19'—Ru2—C20' | 38.49 (11) | C22—C21—C26 | 126.5 (3) |
C21'—Ru2—C20' | 38.25 (11) | C20—C21—Ru1 | 71.06 (16) |
C23'—Ru2—C13 | 123.77 (12) | C22—C21—Ru1 | 70.72 (16) |
C22'—Ru2—C13 | 111.83 (12) | C26—C21—Ru1 | 124.7 (2) |
C19'—Ru2—C13 | 156.68 (12) | C23—C22—C21 | 107.9 (3) |
C21'—Ru2—C13 | 128.76 (12) | C23—C22—C27 | 126.8 (3) |
C20'—Ru2—C13 | 163.55 (12) | C21—C22—C27 | 125.3 (3) |
C23'—Ru2—C14 | 158.07 (12) | C23—C22—Ru1 | 70.63 (17) |
C22'—Ru2—C14 | 126.22 (12) | C21—C22—Ru1 | 70.49 (16) |
C19'—Ru2—C14 | 162.95 (12) | C27—C22—Ru1 | 125.8 (2) |
C21'—Ru2—C14 | 114.54 (12) | C22—C23—C19 | 108.0 (3) |
C20'—Ru2—C14 | 129.80 (12) | C22—C23—C28 | 126.4 (3) |
C13—Ru2—C14 | 37.80 (13) | C19—C23—C28 | 125.6 (3) |
C23'—Ru2—C15 | 161.08 (12) | C22—C23—Ru1 | 70.94 (16) |
C22'—Ru2—C15 | 159.73 (12) | C19—C23—Ru1 | 70.64 (17) |
C19'—Ru2—C15 | 127.93 (11) | C28—C23—Ru1 | 126.2 (2) |
C21'—Ru2—C15 | 126.97 (11) | C19—C24—H24A | 109.5 |
C20'—Ru2—C15 | 113.92 (11) | C19—C24—H24B | 109.5 |
C13—Ru2—C15 | 63.30 (12) | H24A—C24—H24B | 109.5 |
C14—Ru2—C15 | 37.55 (11) | C19—C24—H24C | 109.5 |
C23'—Ru2—C12A | 109.98 (11) | H24A—C24—H24C | 109.5 |
C22'—Ru2—C12A | 126.04 (11) | H24B—C24—H24C | 109.5 |
C19'—Ru2—C12A | 123.33 (11) | C20—C25—H25A | 109.5 |
C21'—Ru2—C12A | 161.85 (11) | C20—C25—H25B | 109.5 |
C20'—Ru2—C12A | 157.52 (11) | H25A—C25—H25B | 109.5 |
C13—Ru2—C12A | 37.99 (11) | C20—C25—H25C | 109.5 |
C14—Ru2—C12A | 63.31 (12) | H25A—C25—H25C | 109.5 |
C15—Ru2—C12A | 63.58 (11) | H25B—C25—H25C | 109.5 |
C23'—Ru2—C15A | 125.97 (11) | C21—C26—H26A | 109.5 |
C22'—Ru2—C15A | 160.36 (11) | C21—C26—H26B | 109.5 |
C19'—Ru2—C15A | 111.32 (11) | H26A—C26—H26B | 109.5 |
C21'—Ru2—C15A | 159.23 (11) | C21—C26—H26C | 109.5 |
C20'—Ru2—C15A | 125.50 (11) | H26A—C26—H26C | 109.5 |
C13—Ru2—C15A | 63.41 (11) | H26B—C26—H26C | 109.5 |
C14—Ru2—C15A | 63.00 (11) | C22—C27—H27A | 109.5 |
C15—Ru2—C15A | 37.84 (10) | C22—C27—H27B | 109.5 |
C12A—Ru2—C15A | 38.12 (10) | H27A—C27—H27B | 109.5 |
C16—C1—C2 | 113.5 (2) | C22—C27—H27C | 109.5 |
C16—C1—H1A | 108.9 | H27A—C27—H27C | 109.5 |
C2—C1—H1A | 108.9 | H27B—C27—H27C | 109.5 |
C16—C1—H1B | 108.9 | C23—C28—H28A | 109.5 |
C2—C1—H1B | 108.9 | C23—C28—H28B | 109.5 |
H1A—C1—H1B | 107.7 | H28A—C28—H28B | 109.5 |
C3—C2—C1 | 113.8 (2) | C23—C28—H28C | 109.5 |
C3—C2—H2A | 108.8 | H28A—C28—H28C | 109.5 |
C1—C2—H2A | 108.8 | H28B—C28—H28C | 109.5 |
C3—C2—H2B | 108.8 | C20'—C19'—C23' | 108.1 (3) |
C1—C2—H2B | 108.8 | C20'—C19'—C24' | 126.3 (3) |
H2A—C2—H2B | 107.7 | C23'—C19'—C24' | 125.6 (3) |
C9—C3—C3A | 116.6 (3) | C20'—C19'—Ru2 | 71.30 (16) |
C9—C3—C2 | 121.6 (3) | C23'—C19'—Ru2 | 70.59 (16) |
C3A—C3—C2 | 120.2 (3) | C24'—C19'—Ru2 | 124.3 (2) |
C4—C3A—C3 | 132.2 (3) | C21'—C20'—C19' | 108.2 (3) |
C4—C3A—C6A | 107.9 (2) | C21'—C20'—C25' | 126.0 (3) |
C3—C3A—C6A | 119.9 (2) | C19'—C20'—C25' | 125.7 (3) |
C4—C3A—Ru1 | 70.34 (15) | C21'—C20'—Ru2 | 70.72 (16) |
C3—C3A—Ru1 | 127.04 (18) | C19'—C20'—Ru2 | 70.21 (16) |
C6A—C3A—Ru1 | 70.08 (14) | C25'—C20'—Ru2 | 128.2 (2) |
C5—C4—C3A | 108.1 (2) | C20'—C21'—C22' | 108.0 (3) |
C5—C4—Ru1 | 71.05 (16) | C20'—C21'—C26' | 125.9 (3) |
C3A—C4—Ru1 | 71.98 (15) | C22'—C21'—C26' | 125.9 (3) |
C5—C4—H4 | 125.9 | C20'—C21'—Ru2 | 71.02 (16) |
C3A—C4—H4 | 125.9 | C22'—C21'—Ru2 | 70.13 (16) |
Ru1—C4—H4 | 122.7 | C26'—C21'—Ru2 | 128.1 (2) |
C4—C5—C6 | 108.8 (3) | C23'—C22'—C21' | 107.7 (3) |
C4—C5—Ru1 | 71.31 (15) | C23'—C22'—C27' | 126.3 (3) |
C6—C5—Ru1 | 70.47 (16) | C21'—C22'—C27' | 126.0 (3) |
C4—C5—H5 | 125.6 | C23'—C22'—Ru2 | 70.63 (16) |
C6—C5—H5 | 125.6 | C21'—C22'—Ru2 | 71.03 (16) |
Ru1—C5—H5 | 124.2 | C27'—C22'—Ru2 | 126.5 (2) |
C5—C6—C6A | 108.2 (3) | C19'—C23'—C22' | 108.0 (3) |
C5—C6—Ru1 | 71.66 (16) | C19'—C23'—C28' | 125.4 (3) |
C6A—C6—Ru1 | 71.61 (15) | C22'—C23'—C28' | 126.5 (3) |
C5—C6—H6 | 125.9 | C19'—C23'—Ru2 | 70.74 (16) |
C6A—C6—H6 | 125.9 | C22'—C23'—Ru2 | 70.66 (16) |
Ru1—C6—H6 | 122.5 | C28'—C23'—Ru2 | 125.7 (2) |
C7—C6A—C6 | 133.2 (3) | C19'—C24'—H24D | 109.5 |
C7—C6A—C3A | 119.9 (2) | C19'—C24'—H24E | 109.5 |
C6—C6A—C3A | 106.9 (2) | H24D—C24'—H24E | 109.5 |
C7—C6A—Ru1 | 124.69 (19) | C19'—C24'—H24F | 109.5 |
C6—C6A—Ru1 | 70.09 (15) | H24D—C24'—H24F | 109.5 |
C3A—C6A—Ru1 | 71.61 (15) | H24E—C24'—H24F | 109.5 |
C8—C7—C6A | 116.6 (3) | C20'—C25'—H25D | 109.5 |
C8—C7—C10 | 121.6 (3) | C20'—C25'—H25E | 109.5 |
C6A—C7—C10 | 120.3 (3) | H25D—C25'—H25E | 109.5 |
C7—C8—C9 | 122.3 (3) | C20'—C25'—H25F | 109.5 |
C7—C8—H8 | 118.9 | H25D—C25'—H25F | 109.5 |
C9—C8—H8 | 118.9 | H25E—C25'—H25F | 109.5 |
C3—C9—C8 | 121.8 (3) | C21'—C26'—H26D | 109.5 |
C3—C9—H9 | 119.1 | C21'—C26'—H26E | 109.5 |
C8—C9—H9 | 119.1 | H26D—C26'—H26E | 109.5 |
C7—C10—C11 | 113.2 (2) | C21'—C26'—H26F | 109.5 |
C7—C10—H10A | 108.9 | H26D—C26'—H26F | 109.5 |
C11—C10—H10A | 108.9 | H26E—C26'—H26F | 109.5 |
C7—C10—H10B | 108.9 | C22'—C27'—H27D | 109.5 |
C11—C10—H10B | 108.9 | C22'—C27'—H27E | 109.5 |
H10A—C10—H10B | 107.8 | H27D—C27'—H27E | 109.5 |
C12—C11—C10 | 113.4 (3) | C22'—C27'—H27F | 109.5 |
C12—C11—H11A | 108.9 | H27D—C27'—H27F | 109.5 |
C10—C11—H11A | 108.9 | H27E—C27'—H27F | 109.5 |
C12—C11—H11B | 108.9 | C23'—C28'—H28D | 109.5 |
C10—C11—H11B | 108.9 | C23'—C28'—H28E | 109.5 |
H11A—C11—H11B | 107.7 | H28D—C28'—H28E | 109.5 |
C18—C12—C12A | 116.3 (3) | C23'—C28'—H28F | 109.5 |
C18—C12—C11 | 120.9 (3) | H28D—C28'—H28F | 109.5 |
C12A—C12—C11 | 121.3 (3) | H28E—C28'—H28F | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Ru2(C10H15)2(C22H18)] |
Mr | 754.94 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 178 |
a, b, c (Å) | 8.647 (2), 13.604 (4), 28.959 (8) |
β (°) | 92.41 (2) |
V (Å3) | 3403.5 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.92 |
Crystal size (mm) | 0.7 × 0.4 × 0.15 |
Data collection | |
Diffractometer | Nicolet R3 diffractometer |
Absorption correction | Part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983) |
Tmin, Tmax | 0.66, 0.84 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11146, 5984, 5079 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.071, 1.05 |
No. of reflections | 5984 |
No. of parameters | 407 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.61 |
Computer programs: P3 (Nicolet, 1987), P3, XDISK (Nicolet, 1987), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), SHELXL97.
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Having prepared and studied various metal complexes of anti-[2.2]indenophanes (Hopf & Dannheim, 1988), we have now prepared ruthenium complexes of syn-[2.2]indenophane, (1). Whereas with the former ligands the metal atoms are oriented in a stepwise fashion, in (1), they were expected to be oriented above each other (eclipsed). Here we present the structure of the doubly-capped ruthenium complex, (3).
The molecule of (3) is shown in Fig. 1. In the following discussion, the rings are defined as ring 1 for atoms C19–C23, ring 2 for C3A/C4/C5/C6/C6A, ring 3 for C12A/C13/C14/C15/C14A, and ring 4 for C19'–C23'; the corresponding centroids are denoted Cent1, Cent2, etc.
The Ru atoms lie 1.795 (1), 1.835 (1), 1.842 (1) and 1.798 (1) Å from the ring planes 1–4, respectively. The general form of the molecule is as expected, in that the four five-membered rings are essentially eclipsed, but there are some deviations from the idealized form (Fig. 2). The sequence Cent1—Ru1—Cent2···Cent3—Ru2—Cent4 is significantly bent at Cent3 (171°), and rings 2 and 3 of the central indenophane ligand are splayed away from each other [interplanar angle 10.92 (4)°]. The distance Cent2···Cent3 is 3.30 Å.
The six-membered rings display the usual flattened boat conformation, in which the bridgehead atoms C3, C7, C12 and C16 lie 0.151 (4), 0.142 (4), 0.149 (4) and 0.151 (4) Å, respectively, out of the plane of the four other atoms; the interplanar angle between the four-atom planes is 1.90 (2)°, and the distance between the corresponding centroids is 3.08 Å.