Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802020615/cf6222sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802020615/cf6222Isup2.hkl |
CCDC reference: 202311
A mixture of lithium tricyclohexylcyclopentadienide (637 mg, 2.0 mmol), molybdenum hexacarbonyl (539 mg, 2.0 mmol), and tetrahydrofuran (50 ml) was stirred at reflux temperature for 5 h and allowed to cool to ambient temperature. Methyl iodide (281 mg, 2.0 mmol) was added and the mixture was heated to reflux temperature for 2 h. The solvent was evaporated and the residue extracted with toluene (30 ml). Evaporation of the filtered toluene solution and recrystallization from hexane–tetrahydrofuran (5:1) at ambient temperature yielded yellow crystalline (I) (712 mg, 1.41 mmol, 70%). C27H38MoO3 (Mr = 506.54), calculated: C 64.02, H 7.56%; found: C 63.31, H 7.64%. 1H NMR (C6D6, 400.13 MHz): 4.75 (s, 2H, ring H), 2.11–0.93 (m, cyclohexyl protons), 0.45 p.p.m. (s, 3H, Mo-methyl). 13C NMR (C6D6, 100.62 MHz): 243.2 (1 C, carbonyl), 229.1 (2 C, carbonyl), 120.9 (s, 1 C, ring C), 117.3 (s, 2 C, ring C), 86.6 (dd, 2 C, J = 163 Hz/5 Hz, ring CH), 37.7 (2 C, methylene), 36.4 (1 C, ipso-CH), 35.7 (2 C, ipso-CH), 35.2 (2 C, cyclohexyl), 34.4 (2 C, cyclohexyl), 27.1 (2 C, cyclohexyl), 27.0 (2 C, cyclohexyl), 26.5 (2 C, cyclohexyl), 26.4 (1 C, cyclohexyl), 26.2 (2 C, cyclohexyl), −14.3 p.p.m. (q, 1 C, J = 136 Hz, Mo-methyl). C,H coupling constants of cyclohexyl carbon signals could not be determined, because of signal superimposition.
Data collection: EXPOSE in IPDS (Stoe & Cie, 1997); cell refinement: CELL in IPDS; data reduction: INTEGRATE in IPDS; program(s) used to solve structure: SIR97 (Altomare et al., 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
[Mo(CH3)(C23H35)(CO)3] | F(000) = 1064 |
Mr = 506.51 | Dx = 1.357 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1480 reflections |
a = 10.8664 (8) Å | θ = 2–25° |
b = 9.8320 (5) Å | µ = 0.55 mm−1 |
c = 23.3279 (17) Å | T = 293 K |
β = 95.838 (9)° | Transparent block, colourless |
V = 2479.4 (3) Å3 | 0.25 × 0.13 × 0.08 mm |
Z = 4 |
Stoe IPDS diffractometer | 4495 independent reflections |
Radiation source: fine-focus sealed tube | 2569 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.097 |
ϕ scans | θmax = 25.4°, θmin = 2.8° |
Absorption correction: analytical (ABST in PLATON; Spek, 2000) | h = −13→13 |
Tmin = 0.922, Tmax = 0.979 | k = −11→11 |
18023 measured reflections | l = −28→28 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.062 | H-atom parameters constrained |
S = 0.80 | w = 1/[σ2(Fo2) + (0.001P)2] where P = (Fo2 + 2Fc2)/3 |
4495 reflections | (Δ/σ)max = 0.001 |
281 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
[Mo(CH3)(C23H35)(CO)3] | V = 2479.4 (3) Å3 |
Mr = 506.51 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.8664 (8) Å | µ = 0.55 mm−1 |
b = 9.8320 (5) Å | T = 293 K |
c = 23.3279 (17) Å | 0.25 × 0.13 × 0.08 mm |
β = 95.838 (9)° |
Stoe IPDS diffractometer | 4495 independent reflections |
Absorption correction: analytical (ABST in PLATON; Spek, 2000) | 2569 reflections with I > 2σ(I) |
Tmin = 0.922, Tmax = 0.979 | Rint = 0.097 |
18023 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.062 | H-atom parameters constrained |
S = 0.80 | Δρmax = 0.47 e Å−3 |
4495 reflections | Δρmin = −0.28 e Å−3 |
281 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 | ||
Mo1 | 0.24948 (3) | 0.78939 (4) | 0.145882 (14) | 0.03463 (9) | |
O1 | 0.4447 (3) | 0.7140 (4) | 0.24899 (13) | 0.0813 (10) | |
O2 | 0.2347 (3) | 1.1055 (4) | 0.14270 (17) | 0.0772 (9) | |
O3 | 0.4941 (3) | 0.8586 (4) | 0.09410 (13) | 0.0709 (10) | |
C1 | 0.1616 (3) | 0.7094 (4) | 0.05652 (12) | 0.0280 (7) | |
C2 | 0.2209 (3) | 0.5972 (4) | 0.08760 (13) | 0.0285 (8) | |
C3 | 0.1556 (3) | 0.5740 (4) | 0.13597 (14) | 0.0335 (9) | |
H3 | 0.1752 | 0.5070 | 0.1635 | 0.040* | |
C4 | 0.0564 (3) | 0.6668 (4) | 0.13684 (14) | 0.0341 (10) | |
C5 | 0.0634 (3) | 0.7522 (3) | 0.08776 (13) | 0.0324 (11) | |
H5 | 0.0112 | 0.8253 | 0.0778 | 0.039* | |
C6 | 0.1743 (4) | 0.8694 (5) | 0.22982 (17) | 0.0606 (13) | |
H6A | 0.2326 | 0.9323 | 0.2488 | 0.091* | |
H6B | 0.1629 | 0.7943 | 0.2550 | 0.091* | |
H6C | 0.0966 | 0.9145 | 0.2202 | 0.091* | |
C7 | 0.3742 (4) | 0.7435 (4) | 0.21102 (18) | 0.0536 (14) | |
C8 | 0.2432 (4) | 0.9871 (5) | 0.1438 (2) | 0.0472 (10) | |
C9 | 0.4041 (4) | 0.8313 (4) | 0.11316 (16) | 0.0478 (11) | |
C11 | 0.1832 (3) | 0.7598 (4) | −0.00255 (13) | 0.0348 (11) | |
H11 | 0.2611 | 0.7204 | −0.0125 | 0.042* | |
C12 | 0.0802 (3) | 0.7078 (5) | −0.04579 (14) | 0.0460 (9) | |
H12A | 0.0780 | 0.6093 | −0.0437 | 0.055* | |
H12B | 0.0018 | 0.7418 | −0.0353 | 0.055* | |
C13 | 0.0942 (4) | 0.7493 (4) | −0.10733 (15) | 0.0584 (15) | |
H13A | 0.1674 | 0.7068 | −0.1199 | 0.070* | |
H13B | 0.0230 | 0.7181 | −0.1323 | 0.070* | |
C14 | 0.1051 (4) | 0.9030 (5) | −0.11199 (18) | 0.0549 (12) | |
H14A | 0.1205 | 0.9272 | −0.1509 | 0.066* | |
H14B | 0.0278 | 0.9449 | −0.1040 | 0.066* | |
C15 | 0.2076 (4) | 0.9558 (5) | −0.07062 (17) | 0.0539 (12) | |
H15A | 0.2098 | 1.0542 | −0.0731 | 0.065* | |
H15B | 0.2858 | 0.9211 | −0.0811 | 0.065* | |
C16 | 0.1919 (4) | 0.9144 (4) | −0.00900 (16) | 0.0497 (11) | |
H16A | 0.2617 | 0.9478 | 0.0163 | 0.060* | |
H16B | 0.1175 | 0.9560 | 0.0027 | 0.060* | |
C21 | 0.3202 (3) | 0.5079 (4) | 0.06751 (14) | 0.0318 (9) | |
H21 | 0.3685 | 0.5633 | 0.0430 | 0.038* | |
C22 | 0.4097 (3) | 0.4487 (5) | 0.11552 (16) | 0.0509 (11) | |
H22A | 0.3637 | 0.3943 | 0.1407 | 0.061* | |
H22B | 0.4486 | 0.5225 | 0.1382 | 0.061* | |
C23 | 0.5096 (3) | 0.3611 (5) | 0.09326 (18) | 0.0561 (13) | |
H23A | 0.5620 | 0.4172 | 0.0717 | 0.067* | |
H23B | 0.5607 | 0.3218 | 0.1256 | 0.067* | |
C24 | 0.4535 (4) | 0.2486 (4) | 0.0550 (2) | 0.0566 (14) | |
H24A | 0.5189 | 0.1992 | 0.0386 | 0.068* | |
H24B | 0.4106 | 0.1853 | 0.0779 | 0.068* | |
C25 | 0.3645 (4) | 0.3035 (5) | 0.00722 (18) | 0.0605 (12) | |
H25A | 0.3255 | 0.2286 | −0.0147 | 0.073* | |
H25B | 0.4092 | 0.3577 | −0.0186 | 0.073* | |
C26 | 0.2646 (3) | 0.3916 (4) | 0.03119 (17) | 0.0495 (11) | |
H26A | 0.2099 | 0.4279 | −0.0006 | 0.059* | |
H26B | 0.2156 | 0.3354 | 0.0544 | 0.059* | |
C41 | −0.0433 (3) | 0.6678 (4) | 0.17624 (15) | 0.0389 (10) | |
H41 | −0.0463 | 0.7595 | 0.1925 | 0.047* | |
C42 | −0.1692 (3) | 0.6404 (5) | 0.14179 (16) | 0.0465 (11) | |
H42A | −0.1843 | 0.7090 | 0.1120 | 0.056* | |
H42B | −0.1670 | 0.5524 | 0.1231 | 0.056* | |
C43 | −0.2740 (4) | 0.6423 (5) | 0.1800 (2) | 0.0682 (15) | |
H43A | −0.3507 | 0.6187 | 0.1573 | 0.082* | |
H43B | −0.2827 | 0.7334 | 0.1951 | 0.082* | |
C44 | −0.2510 (4) | 0.5439 (6) | 0.2294 (2) | 0.0763 (16) | |
H44A | −0.3174 | 0.5509 | 0.2541 | 0.092* | |
H44B | −0.2506 | 0.4518 | 0.2145 | 0.092* | |
C45 | −0.1282 (4) | 0.5730 (6) | 0.26449 (18) | 0.0701 (15) | |
H45A | −0.1134 | 0.5058 | 0.2949 | 0.084* | |
H45B | −0.1311 | 0.6619 | 0.2823 | 0.084* | |
C46 | −0.0244 (3) | 0.5689 (5) | 0.22611 (15) | 0.0463 (11) | |
H46A | 0.0529 | 0.5900 | 0.2489 | 0.056* | |
H46B | −0.0178 | 0.4775 | 0.2111 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mo1 | 0.03622 (15) | 0.03567 (19) | 0.03131 (15) | −0.0015 (2) | 0.00017 (11) | −0.0044 (2) |
O1 | 0.089 (2) | 0.084 (3) | 0.0614 (19) | 0.001 (2) | −0.0402 (17) | 0.005 (2) |
O2 | 0.092 (2) | 0.042 (2) | 0.099 (2) | −0.003 (2) | 0.0153 (18) | −0.004 (2) |
O3 | 0.0519 (18) | 0.088 (3) | 0.076 (2) | −0.0101 (16) | 0.0215 (16) | −0.0055 (18) |
C1 | 0.0279 (16) | 0.026 (2) | 0.0290 (17) | 0.0001 (19) | −0.0009 (13) | −0.003 (2) |
C2 | 0.0288 (18) | 0.025 (2) | 0.032 (2) | −0.0005 (15) | 0.0019 (15) | −0.0037 (16) |
C3 | 0.035 (2) | 0.038 (3) | 0.0274 (19) | 0.0053 (17) | 0.0004 (15) | 0.0015 (17) |
C4 | 0.034 (2) | 0.035 (3) | 0.032 (2) | 0.0007 (16) | −0.0002 (16) | −0.0015 (16) |
C5 | 0.0328 (18) | 0.030 (3) | 0.0337 (19) | 0.0026 (14) | −0.0010 (15) | −0.0009 (15) |
C6 | 0.068 (3) | 0.066 (4) | 0.048 (3) | −0.018 (2) | 0.008 (2) | −0.019 (2) |
C7 | 0.066 (3) | 0.045 (4) | 0.049 (3) | −0.013 (2) | 0.004 (2) | −0.007 (2) |
C8 | 0.050 (2) | 0.041 (3) | 0.050 (2) | −0.005 (3) | 0.0057 (17) | −0.003 (3) |
C9 | 0.060 (3) | 0.045 (3) | 0.037 (2) | 0.003 (2) | −0.006 (2) | −0.0097 (18) |
C11 | 0.0363 (18) | 0.038 (4) | 0.0315 (18) | 0.0078 (15) | 0.0075 (14) | 0.0041 (16) |
C12 | 0.060 (2) | 0.036 (2) | 0.040 (2) | 0.004 (2) | −0.0067 (16) | −0.005 (2) |
C13 | 0.080 (3) | 0.057 (5) | 0.035 (2) | 0.005 (2) | −0.008 (2) | −0.0025 (19) |
C14 | 0.073 (3) | 0.044 (3) | 0.047 (3) | 0.011 (2) | 0.002 (2) | 0.014 (2) |
C15 | 0.059 (3) | 0.044 (3) | 0.057 (3) | −0.003 (2) | −0.002 (2) | 0.021 (2) |
C16 | 0.057 (3) | 0.044 (3) | 0.046 (2) | −0.008 (2) | −0.0058 (19) | 0.003 (2) |
C21 | 0.0277 (18) | 0.031 (3) | 0.038 (2) | −0.0001 (16) | 0.0061 (15) | 0.0040 (17) |
C22 | 0.044 (2) | 0.062 (3) | 0.044 (2) | 0.016 (2) | −0.0063 (18) | 0.002 (2) |
C23 | 0.043 (2) | 0.064 (4) | 0.062 (3) | 0.024 (2) | 0.005 (2) | 0.004 (2) |
C24 | 0.048 (2) | 0.035 (4) | 0.089 (3) | 0.0141 (18) | 0.020 (2) | 0.006 (2) |
C25 | 0.052 (2) | 0.053 (3) | 0.075 (3) | 0.011 (2) | 0.003 (2) | −0.023 (3) |
C26 | 0.044 (2) | 0.042 (3) | 0.061 (3) | 0.009 (2) | −0.0007 (19) | −0.014 (2) |
C41 | 0.035 (2) | 0.044 (3) | 0.038 (2) | 0.0016 (16) | 0.0043 (16) | −0.0018 (17) |
C42 | 0.042 (2) | 0.055 (3) | 0.041 (2) | 0.000 (2) | 0.0034 (18) | 0.005 (2) |
C43 | 0.040 (2) | 0.082 (4) | 0.085 (4) | 0.002 (2) | 0.015 (2) | −0.002 (3) |
C44 | 0.065 (3) | 0.090 (5) | 0.080 (4) | −0.012 (3) | 0.035 (3) | 0.006 (3) |
C45 | 0.066 (3) | 0.097 (5) | 0.049 (3) | −0.001 (3) | 0.016 (2) | 0.011 (3) |
C46 | 0.045 (2) | 0.057 (3) | 0.038 (2) | −0.002 (2) | 0.0124 (17) | 0.008 (2) |
Mo1—C8 | 1.946 (5) | C15—H15A | 0.970 |
Mo1—C9 | 1.958 (5) | C15—H15B | 0.970 |
Mo1—C7 | 1.982 (4) | C16—H16A | 0.970 |
Mo1—C6 | 2.333 (4) | C16—H16B | 0.970 |
Mo1—C2 | 2.330 (3) | C21—C22 | 1.523 (4) |
Mo1—C1 | 2.339 (3) | C21—C26 | 1.512 (5) |
Mo1—C5 | 2.346 (3) | C21—H21 | 0.980 |
Mo1—C3 | 2.351 (4) | C22—C23 | 1.518 (5) |
Mo1—C4 | 2.411 (3) | C22—H22A | 0.970 |
O1—C7 | 1.148 (4) | C22—H22B | 0.970 |
O2—C8 | 1.168 (4) | C23—C24 | 1.510 (6) |
O3—C9 | 1.147 (4) | C23—H23A | 0.970 |
C1—C5 | 1.416 (4) | C23—H23B | 0.970 |
C1—C2 | 1.436 (5) | C24—C25 | 1.500 (6) |
C1—C11 | 1.505 (4) | C24—H24A | 0.970 |
C2—C3 | 1.411 (4) | C24—H24B | 0.970 |
C2—C21 | 1.502 (4) | C25—C26 | 1.538 (5) |
C3—C4 | 1.414 (5) | C25—H25A | 0.970 |
C3—H3 | 0.930 | C25—H25B | 0.970 |
C4—C5 | 1.428 (4) | C26—H26A | 0.970 |
C4—C41 | 1.490 (5) | C26—H26B | 0.970 |
C5—H5 | 0.930 | C41—C46 | 1.514 (5) |
C6—H6A | 0.960 | C41—C42 | 1.538 (5) |
C6—H6B | 0.960 | C41—H41 | 0.980 |
C6—H6C | 0.960 | C42—C43 | 1.516 (5) |
C11—C16 | 1.531 (5) | C42—H42A | 0.970 |
C11—C12 | 1.517 (5) | C42—H42B | 0.970 |
C11—H11 | 0.980 | C43—C44 | 1.506 (6) |
C12—C13 | 1.515 (5) | C43—H43A | 0.970 |
C12—H12A | 0.970 | C43—H43B | 0.970 |
C12—H12B | 0.970 | C44—C45 | 1.520 (6) |
C13—C14 | 1.521 (6) | C44—H44A | 0.970 |
C13—H13A | 0.970 | C44—H44B | 0.970 |
C13—H13B | 0.970 | C45—C46 | 1.511 (5) |
C14—C15 | 1.490 (5) | C45—H45A | 0.970 |
C14—H14A | 0.970 | C45—H45B | 0.970 |
C14—H14B | 0.970 | C46—H46A | 0.970 |
C15—C16 | 1.520 (5) | C46—H46B | 0.970 |
C8—Mo1—C9 | 79.00 (18) | H13A—C13—H13B | 108.1 |
C8—Mo1—C7 | 105.43 (19) | C15—C14—C13 | 111.0 (3) |
C9—Mo1—C7 | 78.46 (16) | C15—C14—H14A | 109.4 |
C8—Mo1—C6 | 70.73 (18) | C13—C14—H14A | 109.4 |
C9—Mo1—C6 | 130.04 (15) | C15—C14—H14B | 109.4 |
C7—Mo1—C6 | 72.77 (16) | C13—C14—H14B | 109.4 |
C8—Mo1—C2 | 142.50 (16) | H14A—C14—H14B | 108.0 |
C9—Mo1—C2 | 90.68 (13) | C14—C15—C16 | 111.8 (3) |
C7—Mo1—C2 | 107.63 (15) | C14—C15—H15A | 109.3 |
C6—Mo1—C2 | 136.53 (13) | C16—C15—H15A | 109.3 |
C8—Mo1—C1 | 107.66 (17) | C14—C15—H15B | 109.3 |
C9—Mo1—C1 | 90.68 (13) | C16—C15—H15B | 109.3 |
C7—Mo1—C1 | 142.36 (15) | H15A—C15—H15B | 107.9 |
C6—Mo1—C1 | 135.67 (12) | C11—C16—C15 | 111.9 (3) |
C2—Mo1—C1 | 35.83 (12) | C11—C16—H16A | 109.2 |
C8—Mo1—C5 | 96.60 (16) | C15—C16—H16A | 109.2 |
C9—Mo1—C5 | 122.05 (13) | C11—C16—H16B | 109.2 |
C7—Mo1—C5 | 152.81 (14) | C15—C16—H16B | 109.2 |
C6—Mo1—C5 | 100.54 (13) | H16A—C16—H16B | 107.9 |
C2—Mo1—C5 | 58.71 (11) | C2—C21—C22 | 114.8 (3) |
C1—Mo1—C5 | 35.20 (10) | C2—C21—C26 | 111.0 (3) |
C8—Mo1—C3 | 152.06 (16) | C22—C21—C26 | 108.2 (3) |
C9—Mo1—C3 | 122.14 (14) | C2—C21—H21 | 107.5 |
C7—Mo1—C3 | 97.27 (15) | C22—C21—H21 | 107.5 |
C6—Mo1—C3 | 101.58 (14) | C26—C21—H21 | 107.5 |
C2—Mo1—C3 | 35.08 (11) | C21—C22—C23 | 113.0 (3) |
C1—Mo1—C3 | 58.40 (13) | C21—C22—H22A | 109.0 |
C5—Mo1—C3 | 57.53 (12) | C23—C22—H22A | 109.0 |
C8—Mo1—C4 | 117.99 (16) | C21—C22—H22B | 109.0 |
C9—Mo1—C4 | 147.64 (13) | C23—C22—H22B | 109.0 |
C7—Mo1—C4 | 118.33 (15) | H22A—C22—H22B | 107.8 |
C6—Mo1—C4 | 82.31 (13) | C24—C23—C22 | 111.0 (3) |
C2—Mo1—C4 | 58.69 (11) | C24—C23—H23A | 109.4 |
C1—Mo1—C4 | 58.75 (11) | C22—C23—H23A | 109.4 |
C5—Mo1—C4 | 34.92 (11) | C24—C23—H23B | 109.4 |
C3—Mo1—C4 | 34.52 (11) | C22—C23—H23B | 109.4 |
C5—C1—C2 | 106.9 (3) | H23A—C23—H23B | 108.0 |
C5—C1—C11 | 124.7 (3) | C25—C24—C23 | 111.5 (4) |
C2—C1—C11 | 127.7 (3) | C25—C24—H24A | 109.3 |
C5—C1—Mo1 | 72.67 (18) | C23—C24—H24A | 109.3 |
C2—C1—Mo1 | 71.77 (17) | C25—C24—H24B | 109.3 |
C11—C1—Mo1 | 128.2 (2) | C23—C24—H24B | 109.3 |
C3—C2—C1 | 106.9 (3) | H24A—C24—H24B | 108.0 |
C3—C2—C21 | 126.2 (3) | C24—C25—C26 | 111.0 (3) |
C1—C2—C21 | 126.2 (3) | C24—C25—H25A | 109.4 |
C3—C2—Mo1 | 73.3 (2) | C26—C25—H25A | 109.4 |
C1—C2—Mo1 | 72.4 (2) | C24—C25—H25B | 109.4 |
C21—C2—Mo1 | 126.8 (2) | C26—C25—H25B | 109.4 |
C4—C3—C2 | 110.7 (3) | H25A—C25—H25B | 108.0 |
C4—C3—Mo1 | 75.0 (2) | C21—C26—C25 | 111.9 (3) |
C2—C3—Mo1 | 71.6 (2) | C21—C26—H26A | 109.2 |
C4—C3—H3 | 124.6 | C25—C26—H26A | 109.2 |
C2—C3—H3 | 124.6 | C21—C26—H26B | 109.2 |
Mo1—C3—H3 | 120.3 | C25—C26—H26B | 109.2 |
C3—C4—C5 | 105.3 (3) | H26A—C26—H26B | 107.9 |
C3—C4—C41 | 128.0 (3) | C4—C41—C46 | 114.8 (3) |
C5—C4—C41 | 126.3 (3) | C4—C41—C42 | 109.9 (3) |
C3—C4—Mo1 | 70.4 (2) | C46—C41—C42 | 109.5 (3) |
C5—C4—Mo1 | 70.05 (18) | C4—C41—H41 | 107.5 |
C41—C4—Mo1 | 128.6 (2) | C46—C41—H41 | 107.5 |
C1—C5—C4 | 110.0 (3) | C42—C41—H41 | 107.5 |
C1—C5—Mo1 | 72.13 (17) | C43—C42—C41 | 111.8 (3) |
C4—C5—Mo1 | 75.03 (18) | C43—C42—H42A | 109.3 |
C1—C5—H5 | 125.0 | C41—C42—H42A | 109.3 |
C4—C5—H5 | 125.0 | C43—C42—H42B | 109.3 |
Mo1—C5—H5 | 119.5 | C41—C42—H42B | 109.3 |
Mo1—C6—H6A | 109.5 | H42A—C42—H42B | 107.9 |
Mo1—C6—H6B | 109.5 | C42—C43—C44 | 111.5 (4) |
H6A—C6—H6B | 109.5 | C42—C43—H43A | 109.3 |
Mo1—C6—H6C | 109.5 | C44—C43—H43A | 109.3 |
H6A—C6—H6C | 109.5 | C42—C43—H43B | 109.3 |
H6B—C6—H6C | 109.5 | C44—C43—H43B | 109.3 |
O1—C7—Mo1 | 178.2 (4) | H43A—C43—H43B | 108.0 |
O2—C8—Mo1 | 177.5 (4) | C45—C44—C43 | 111.1 (4) |
O3—C9—Mo1 | 178.7 (4) | C45—C44—H44A | 109.4 |
C1—C11—C16 | 115.7 (3) | C43—C44—H44A | 109.4 |
C1—C11—C12 | 109.0 (3) | C45—C44—H44B | 109.4 |
C16—C11—C12 | 108.5 (3) | C43—C44—H44B | 109.4 |
C1—C11—H11 | 107.8 | H44A—C44—H44B | 108.0 |
C16—C11—H11 | 107.8 | C44—C45—C46 | 110.1 (4) |
C12—C11—H11 | 107.8 | C44—C45—H45A | 109.6 |
C13—C12—C11 | 113.7 (3) | C46—C45—H45A | 109.6 |
C13—C12—H12A | 108.8 | C44—C45—H45B | 109.6 |
C11—C12—H12A | 108.8 | C46—C45—H45B | 109.6 |
C13—C12—H12B | 108.8 | H45A—C45—H45B | 108.2 |
C11—C12—H12B | 108.8 | C41—C46—C45 | 112.8 (3) |
H12A—C12—H12B | 107.7 | C41—C46—H46A | 109.0 |
C14—C13—C12 | 110.6 (3) | C45—C46—H46A | 109.0 |
C14—C13—H13A | 109.5 | C41—C46—H46B | 109.0 |
C12—C13—H13A | 109.5 | C45—C46—H46B | 109.0 |
C14—C13—H13B | 109.5 | H46A—C46—H46B | 107.8 |
C12—C13—H13B | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Mo(CH3)(C23H35)(CO)3] |
Mr | 506.51 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 10.8664 (8), 9.8320 (5), 23.3279 (17) |
β (°) | 95.838 (9) |
V (Å3) | 2479.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.55 |
Crystal size (mm) | 0.25 × 0.13 × 0.08 |
Data collection | |
Diffractometer | Stoe IPDS diffractometer |
Absorption correction | Analytical (ABST in PLATON; Spek, 2000) |
Tmin, Tmax | 0.922, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18023, 4495, 2569 |
Rint | 0.097 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.062, 0.80 |
No. of reflections | 4495 |
No. of parameters | 281 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.28 |
Computer programs: EXPOSE in IPDS (Stoe & Cie, 1997), CELL in IPDS, INTEGRATE in IPDS, SIR97 (Altomare et al., 1998), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
The title compound, (I), is the first known half-sandwich complex of the 1,2,4-tricyclohexylcyclopentadienyl ligand. The perpendicular distance of Mo from the five-membered ring plane [2.0206 (15) Å] and all Mo—C distances are comparable to the values found for other tricarbonyl(cyclopentadienyl)methylmolybdenum derivatives (El Mouatassim et al., 1995; Lai et al., 1993; Bell et al., 1988). All cyclohexyl (Cy) substituents exhibit a chair conformation. The angles between the cyclopentadienyl ring plane and one plane for each substituent, defined by the cyclopentadienyl ring atom connected to the ipso-C atom and the two nearest methylene C atoms, are 83.17 (13)° for 1-Cy and 68.27 (14)° for 2-Cy. With these two substituents rotated away from each other, a maximum of space is provided for carbonyl C9—O3. The Cy substituent in the 4-position adopts a dihedral angle of 41.91 (18)° with the Cp ring plane, avoiding any close contact with the methyl group bonded to Mo. The absence of steric strain has also been noted for hexa(cyclohexyl)ferrocene, the only other known complex of the 1,2,4-tricyclohexacyclopentadienyl ligand (Burman et al., 1994).