Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803001016/bt6227sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803001016/bt62273sup2.hkl |
CCDC reference: 204699
Compound (3) was obtained as described by Höpfner (1996) and recrystallized from methanol.
Methyl H atoms were identified in difference syntheses, idealized and then refined using rigid methyl groups (C—H = 0.98 Å and H—C—H = 109.5°) Other H atoms were included using a riding model with fixed C—H bond lengths of 0.95 Å; Uiso(H) values were fixed at 1.2 times the Ueq values of the parent atom. The bond lengths of the methylethenyl substituent, and the fact that the largest difference peaks were at bonding distance to C17 and C17' (the corresponding methyl H atoms were the least well resolved) may indicate some disorder between the methylene and methyl sites C17 and C18 (and C17' and C18').
Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1996); software used to prepare material for publication: SHELXL97.
C24H36 | F(000) = 1440 |
Mr = 324.53 | Dx = 1.035 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.382 (2) Å | Cell parameters from 54 reflections |
b = 17.062 (2) Å | θ = 10–11° |
c = 17.053 (2) Å | µ = 0.06 mm−1 |
β = 95.436 (12)° | T = 143 K |
V = 4165.6 (9) Å3 | Prism, colourless |
Z = 8 | 0.6 × 0.5 × 0.4 mm |
Stoe Stadi-4 diffractometer | Rint = 0.025 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 3.1° |
Graphite monochromator | h = −17→17 |
ω–θ scans | k = 0→20 |
7622 measured reflections | l = −20→1 |
7330 independent reflections | 3 standard reflections every 60 min |
4782 reflections with I > 2σ(I) | 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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0543P)2 + 2.454P] where P = (Fo2 + 2Fc2)/3 |
7330 reflections | (Δ/σ)max = 0.036 |
455 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C24H36 | V = 4165.6 (9) Å3 |
Mr = 324.53 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.382 (2) Å | µ = 0.06 mm−1 |
b = 17.062 (2) Å | T = 143 K |
c = 17.053 (2) Å | 0.6 × 0.5 × 0.4 mm |
β = 95.436 (12)° |
Stoe Stadi-4 diffractometer | Rint = 0.025 |
7622 measured reflections | 3 standard reflections every 60 min |
7330 independent reflections | intensity decay: none |
4782 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.29 e Å−3 |
7330 reflections | Δρmin = −0.27 e Å−3 |
455 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 | ||
C1 | 0.20134 (16) | 0.64983 (13) | 0.24293 (13) | 0.0223 (5) | |
C2 | 0.25543 (16) | 0.60076 (14) | 0.30790 (13) | 0.0219 (5) | |
C3 | 0.23382 (16) | 0.52548 (14) | 0.32256 (13) | 0.0220 (5) | |
C4 | 0.16990 (16) | 0.48270 (13) | 0.26335 (13) | 0.0226 (5) | |
C5 | 0.18062 (16) | 0.51489 (13) | 0.18318 (13) | 0.0220 (5) | |
C6 | 0.14962 (16) | 0.59804 (14) | 0.17881 (14) | 0.0229 (5) | |
C7 | 0.13380 (18) | 0.70126 (15) | 0.28646 (15) | 0.0309 (6) | |
H7A | 0.1671 | 0.7228 | 0.3345 | 0.037* | |
H7B | 0.0813 | 0.6692 | 0.3004 | 0.037* | |
H7C | 0.1103 | 0.7443 | 0.2520 | 0.037* | |
C8 | 0.27032 (18) | 0.70094 (15) | 0.20212 (15) | 0.0318 (6) | |
H8A | 0.3010 | 0.7378 | 0.2403 | 0.038* | |
H8B | 0.2365 | 0.7302 | 0.1589 | 0.038* | |
H8C | 0.3175 | 0.6674 | 0.1811 | 0.038* | |
C9 | 0.32968 (18) | 0.64425 (15) | 0.35538 (14) | 0.0282 (6) | |
H9 | 0.3104 | 0.6896 | 0.3818 | 0.034* | |
C10 | 0.41966 (19) | 0.62747 (16) | 0.36537 (16) | 0.0352 (6) | |
C11 | 0.27873 (17) | 0.48101 (15) | 0.39150 (14) | 0.0286 (6) | |
C12 | 0.10868 (17) | 0.42621 (14) | 0.27783 (15) | 0.0275 (6) | |
C13 | 0.22378 (18) | 0.47683 (15) | 0.12826 (14) | 0.0293 (6) | |
C14 | 0.08328 (17) | 0.62306 (15) | 0.12419 (14) | 0.0274 (6) | |
C15 | 0.4866 (2) | 0.6785 (2) | 0.41532 (19) | 0.0556 (9) | |
H15A | 0.4529 | 0.7234 | 0.4347 | 0.067* | |
H15B | 0.5356 | 0.6973 | 0.3837 | 0.067* | |
H15C | 0.5150 | 0.6482 | 0.4601 | 0.067* | |
C16 | 0.4632 (2) | 0.55855 (17) | 0.3292 (2) | 0.0494 (8) | |
H16A | 0.4801 | 0.5192 | 0.3699 | 0.059* | |
H16B | 0.5195 | 0.5754 | 0.3056 | 0.059* | |
H16C | 0.4187 | 0.5358 | 0.2884 | 0.059* | |
C17 | 0.2757 (2) | 0.51297 (18) | 0.47073 (15) | 0.0481 (8) | |
H17A | 0.3119 | 0.4792 | 0.5088 | 0.058* | |
H17B | 0.2107 | 0.5153 | 0.4835 | 0.058* | |
H17C | 0.3024 | 0.5658 | 0.4730 | 0.058* | |
C18 | 0.31915 (19) | 0.40983 (16) | 0.38042 (16) | 0.0369 (7) | |
H18A | 0.3456 | 0.3806 | 0.4245 | 0.044* | |
H18B | 0.3208 | 0.3896 | 0.3287 | 0.044* | |
C19 | 0.09067 (19) | 0.39797 (16) | 0.35839 (15) | 0.0346 (6) | |
H19A | 0.1186 | 0.3460 | 0.3676 | 0.042* | |
H19B | 0.0232 | 0.3948 | 0.3620 | 0.042* | |
H19C | 0.1185 | 0.4347 | 0.3981 | 0.042* | |
C20 | 0.04864 (19) | 0.38616 (16) | 0.21281 (17) | 0.0370 (7) | |
H20A | 0.0623 | 0.4077 | 0.1619 | 0.044* | |
H20B | −0.0173 | 0.3948 | 0.2201 | 0.044* | |
H20C | 0.0618 | 0.3298 | 0.2141 | 0.044* | |
C21 | 0.2578 (2) | 0.39357 (15) | 0.13865 (16) | 0.0394 (7) | |
H21A | 0.2530 | 0.3769 | 0.1931 | 0.047* | |
H21B | 0.3231 | 0.3905 | 0.1269 | 0.047* | |
H21C | 0.2194 | 0.3592 | 0.1027 | 0.047* | |
C22 | 0.2438 (2) | 0.51301 (17) | 0.05137 (15) | 0.0375 (7) | |
H22A | 0.2052 | 0.4876 | 0.0082 | 0.045* | |
H22B | 0.3099 | 0.5059 | 0.0438 | 0.045* | |
H22C | 0.2292 | 0.5691 | 0.0520 | 0.045* | |
C23 | 0.03249 (19) | 0.56951 (16) | 0.06454 (15) | 0.0379 (7) | |
H23A | 0.0511 | 0.5815 | 0.0121 | 0.045* | |
H23B | −0.0350 | 0.5772 | 0.0648 | 0.045* | |
H23C | 0.0483 | 0.5149 | 0.0779 | 0.045* | |
C24 | 0.0478 (2) | 0.70605 (16) | 0.11344 (16) | 0.0386 (7) | |
H24A | −0.0096 | 0.7121 | 0.1396 | 0.046* | |
H24B | 0.0347 | 0.7173 | 0.0571 | 0.046* | |
H24C | 0.0952 | 0.7426 | 0.1367 | 0.046* | |
C1' | 0.30796 (16) | 0.88366 (14) | 0.77252 (14) | 0.0239 (5) | |
C2' | 0.25355 (16) | 0.83892 (14) | 0.70453 (13) | 0.0226 (5) | |
C3' | 0.27110 (16) | 0.76316 (14) | 0.68756 (13) | 0.0226 (5) | |
C4' | 0.33046 (16) | 0.71599 (13) | 0.74610 (13) | 0.0218 (5) | |
C5' | 0.31981 (16) | 0.74614 (14) | 0.82705 (14) | 0.0235 (5) | |
C6' | 0.35559 (16) | 0.82765 (14) | 0.83554 (13) | 0.0227 (5) | |
C7' | 0.37930 (18) | 0.93452 (15) | 0.73317 (15) | 0.0325 (6) | |
H7'1 | 0.3484 | 0.9594 | 0.6858 | 0.039* | |
H7'2 | 0.4306 | 0.9014 | 0.7186 | 0.039* | |
H7'3 | 0.4041 | 0.9751 | 0.7701 | 0.039* | |
C8' | 0.23969 (18) | 0.93598 (15) | 0.81307 (15) | 0.0331 (6) | |
H8'1 | 0.2106 | 0.9737 | 0.7749 | 0.040* | |
H8'2 | 0.2738 | 0.9642 | 0.8568 | 0.040* | |
H8'3 | 0.1912 | 0.9033 | 0.8333 | 0.040* | |
C9' | 0.18299 (18) | 0.88555 (15) | 0.65556 (14) | 0.0289 (6) | |
H9' | 0.2052 | 0.9305 | 0.6303 | 0.035* | |
C10' | 0.09208 (19) | 0.87104 (16) | 0.64331 (16) | 0.0356 (7) | |
C11' | 0.22586 (17) | 0.72332 (15) | 0.61578 (14) | 0.0263 (6) | |
C12' | 0.38889 (17) | 0.65805 (14) | 0.73057 (14) | 0.0258 (6) | |
C13' | 0.27311 (18) | 0.70862 (15) | 0.87967 (14) | 0.0286 (6) | |
C14' | 0.42218 (17) | 0.84749 (15) | 0.89223 (14) | 0.0290 (6) | |
C15' | 0.0288 (2) | 0.9219 (2) | 0.58928 (19) | 0.0567 (9) | |
H15D | 0.0650 | 0.9651 | 0.5696 | 0.068* | |
H15E | −0.0212 | 0.9431 | 0.6183 | 0.068* | |
H15F | 0.0015 | 0.8905 | 0.5448 | 0.068* | |
C16' | 0.0444 (2) | 0.80442 (18) | 0.6800 (2) | 0.0485 (8) | |
H16D | 0.0880 | 0.7793 | 0.7199 | 0.058* | |
H16E | 0.0235 | 0.7660 | 0.6393 | 0.058* | |
H16F | −0.0098 | 0.8242 | 0.7048 | 0.058* | |
C17' | 0.2360 (2) | 0.75746 (17) | 0.53835 (15) | 0.0394 (7) | |
H17D | 0.2076 | 0.7225 | 0.4972 | 0.047* | |
H17E | 0.3025 | 0.7641 | 0.5317 | 0.047* | |
H17F | 0.2049 | 0.8086 | 0.5343 | 0.047* | |
C18' | 0.17941 (18) | 0.65451 (16) | 0.62295 (16) | 0.0339 (6) | |
H18C | 0.1530 | 0.6279 | 0.5772 | 0.041* | |
H18D | 0.1734 | 0.6331 | 0.6737 | 0.041* | |
C19' | 0.40771 (18) | 0.63178 (15) | 0.64908 (15) | 0.0309 (6) | |
H19D | 0.3789 | 0.5804 | 0.6380 | 0.037* | |
H19E | 0.4753 | 0.6279 | 0.6461 | 0.037* | |
H19F | 0.3812 | 0.6699 | 0.6102 | 0.037* | |
C20' | 0.4447 (2) | 0.61292 (16) | 0.79430 (17) | 0.0395 (7) | |
H20D | 0.4299 | 0.6319 | 0.8459 | 0.047* | |
H20E | 0.5115 | 0.6203 | 0.7893 | 0.047* | |
H20F | 0.4292 | 0.5571 | 0.7893 | 0.047* | |
C21' | 0.2342 (2) | 0.62724 (16) | 0.86563 (16) | 0.0405 (7) | |
H21D | 0.2401 | 0.6119 | 0.8109 | 0.049* | |
H21E | 0.1682 | 0.6266 | 0.8755 | 0.049* | |
H21F | 0.2691 | 0.5903 | 0.9013 | 0.049* | |
C22' | 0.2546 (2) | 0.74269 (18) | 0.95819 (15) | 0.0400 (7) | |
H22D | 0.2931 | 0.7156 | 1.0003 | 0.048* | |
H22E | 0.1884 | 0.7360 | 0.9661 | 0.048* | |
H22F | 0.2701 | 0.7986 | 0.9593 | 0.048* | |
C23' | 0.46983 (19) | 0.78845 (17) | 0.94823 (15) | 0.0376 (7) | |
H23D | 0.4527 | 0.7354 | 0.9302 | 0.045* | |
H23E | 0.4501 | 0.7966 | 1.0011 | 0.045* | |
H23F | 0.5377 | 0.7949 | 0.9498 | 0.045* | |
C24' | 0.4618 (2) | 0.92882 (16) | 0.90898 (17) | 0.0404 (7) | |
H24D | 0.5205 | 0.9345 | 0.8846 | 0.048* | |
H24E | 0.4735 | 0.9364 | 0.9660 | 0.048* | |
H24F | 0.4169 | 0.9682 | 0.8871 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0244 (13) | 0.0180 (12) | 0.0243 (12) | −0.0009 (10) | 0.0017 (10) | −0.0014 (10) |
C2 | 0.0243 (13) | 0.0213 (13) | 0.0203 (12) | 0.0028 (10) | 0.0029 (10) | −0.0039 (10) |
C3 | 0.0233 (12) | 0.0214 (13) | 0.0217 (12) | 0.0034 (10) | 0.0046 (10) | 0.0007 (10) |
C4 | 0.0260 (13) | 0.0177 (12) | 0.0244 (12) | 0.0035 (10) | 0.0032 (10) | 0.0002 (10) |
C5 | 0.0231 (12) | 0.0200 (12) | 0.0221 (12) | −0.0019 (10) | −0.0022 (10) | 0.0015 (10) |
C6 | 0.0252 (13) | 0.0203 (13) | 0.0234 (12) | −0.0033 (10) | 0.0033 (10) | 0.0021 (10) |
C7 | 0.0322 (14) | 0.0257 (14) | 0.0346 (15) | 0.0058 (11) | 0.0023 (12) | −0.0043 (11) |
C8 | 0.0320 (14) | 0.0270 (14) | 0.0363 (15) | −0.0064 (12) | 0.0015 (12) | 0.0038 (12) |
C9 | 0.0365 (15) | 0.0230 (13) | 0.0244 (13) | −0.0002 (11) | −0.0007 (11) | −0.0054 (11) |
C10 | 0.0341 (15) | 0.0335 (16) | 0.0361 (15) | −0.0046 (12) | −0.0064 (12) | −0.0004 (12) |
C11 | 0.0321 (14) | 0.0283 (14) | 0.0252 (13) | −0.0063 (12) | 0.0010 (11) | 0.0050 (11) |
C12 | 0.0282 (14) | 0.0211 (13) | 0.0330 (14) | 0.0011 (11) | 0.0018 (11) | 0.0022 (11) |
C13 | 0.0351 (15) | 0.0268 (14) | 0.0257 (13) | −0.0031 (11) | 0.0020 (11) | −0.0031 (11) |
C14 | 0.0296 (14) | 0.0251 (14) | 0.0271 (13) | −0.0017 (11) | 0.0016 (11) | 0.0014 (11) |
C15 | 0.0446 (19) | 0.058 (2) | 0.060 (2) | −0.0089 (16) | −0.0211 (16) | −0.0037 (17) |
C16 | 0.0311 (16) | 0.0401 (18) | 0.078 (2) | 0.0010 (14) | 0.0079 (15) | −0.0018 (16) |
C17 | 0.070 (2) | 0.0478 (19) | 0.0254 (15) | −0.0008 (17) | 0.0008 (14) | 0.0055 (14) |
C18 | 0.0439 (17) | 0.0316 (15) | 0.0339 (15) | 0.0058 (13) | −0.0035 (13) | 0.0079 (12) |
C19 | 0.0333 (15) | 0.0320 (15) | 0.0394 (16) | −0.0003 (12) | 0.0082 (12) | 0.0073 (12) |
C20 | 0.0363 (15) | 0.0270 (15) | 0.0468 (17) | −0.0058 (12) | −0.0009 (13) | 0.0016 (13) |
C21 | 0.0557 (19) | 0.0297 (15) | 0.0333 (15) | 0.0073 (14) | 0.0066 (13) | −0.0042 (12) |
C22 | 0.0459 (17) | 0.0399 (17) | 0.0276 (14) | 0.0002 (14) | 0.0082 (12) | −0.0015 (12) |
C23 | 0.0422 (16) | 0.0389 (17) | 0.0303 (15) | 0.0013 (13) | −0.0085 (12) | −0.0012 (13) |
C24 | 0.0401 (16) | 0.0334 (16) | 0.0402 (16) | 0.0031 (13) | −0.0071 (13) | 0.0080 (13) |
C1' | 0.0244 (13) | 0.0193 (12) | 0.0283 (13) | −0.0011 (10) | 0.0042 (10) | −0.0019 (10) |
C2' | 0.0245 (13) | 0.0205 (13) | 0.0231 (12) | −0.0008 (10) | 0.0042 (10) | 0.0018 (10) |
C3' | 0.0229 (12) | 0.0249 (13) | 0.0205 (12) | −0.0030 (10) | 0.0048 (10) | 0.0019 (10) |
C4' | 0.0241 (12) | 0.0171 (12) | 0.0239 (12) | −0.0031 (10) | 0.0004 (10) | 0.0009 (10) |
C5' | 0.0247 (13) | 0.0213 (13) | 0.0238 (13) | 0.0018 (10) | −0.0012 (10) | 0.0026 (10) |
C6' | 0.0250 (13) | 0.0206 (13) | 0.0234 (12) | 0.0011 (10) | 0.0070 (10) | −0.0024 (10) |
C7' | 0.0343 (15) | 0.0263 (14) | 0.0367 (15) | −0.0066 (12) | 0.0019 (12) | 0.0036 (12) |
C8' | 0.0359 (15) | 0.0288 (15) | 0.0345 (15) | 0.0072 (12) | 0.0025 (12) | −0.0076 (12) |
C9' | 0.0380 (15) | 0.0213 (13) | 0.0266 (13) | 0.0020 (11) | −0.0009 (11) | 0.0002 (11) |
C10' | 0.0332 (15) | 0.0324 (15) | 0.0397 (16) | 0.0075 (12) | −0.0051 (12) | −0.0091 (13) |
C11' | 0.0270 (13) | 0.0279 (14) | 0.0234 (13) | 0.0051 (11) | −0.0010 (10) | −0.0025 (11) |
C12' | 0.0268 (13) | 0.0187 (12) | 0.0310 (14) | −0.0035 (11) | −0.0025 (11) | −0.0022 (11) |
C13' | 0.0329 (14) | 0.0266 (14) | 0.0252 (13) | −0.0036 (11) | −0.0023 (11) | 0.0045 (11) |
C14' | 0.0299 (14) | 0.0317 (15) | 0.0255 (13) | −0.0015 (12) | 0.0031 (11) | −0.0056 (11) |
C15' | 0.053 (2) | 0.051 (2) | 0.060 (2) | 0.0199 (16) | −0.0248 (17) | −0.0081 (17) |
C16' | 0.0267 (15) | 0.0463 (19) | 0.072 (2) | 0.0005 (14) | 0.0036 (14) | −0.0132 (17) |
C17' | 0.0482 (18) | 0.0431 (17) | 0.0264 (14) | 0.0057 (14) | 0.0013 (13) | −0.0007 (13) |
C18' | 0.0344 (15) | 0.0333 (15) | 0.0332 (15) | −0.0035 (12) | −0.0014 (12) | −0.0113 (12) |
C19' | 0.0304 (14) | 0.0235 (14) | 0.0390 (15) | 0.0033 (11) | 0.0050 (12) | −0.0055 (12) |
C20' | 0.0401 (16) | 0.0318 (16) | 0.0444 (17) | 0.0104 (13) | −0.0069 (13) | −0.0037 (13) |
C21' | 0.0534 (19) | 0.0351 (16) | 0.0328 (15) | −0.0122 (14) | 0.0040 (13) | 0.0079 (13) |
C22' | 0.0439 (17) | 0.0469 (18) | 0.0305 (15) | −0.0029 (14) | 0.0105 (13) | 0.0044 (13) |
C23' | 0.0379 (16) | 0.0428 (17) | 0.0299 (14) | −0.0021 (13) | −0.0085 (12) | −0.0045 (13) |
C24' | 0.0435 (17) | 0.0374 (16) | 0.0393 (16) | −0.0076 (14) | −0.0013 (13) | −0.0136 (13) |
C1—C8 | 1.536 (3) | C1'—C2' | 1.539 (3) |
C1—C2 | 1.540 (3) | C1'—C8' | 1.539 (3) |
C1—C6 | 1.541 (3) | C1'—C7' | 1.545 (3) |
C1—C7 | 1.550 (3) | C1'—C6' | 1.548 (3) |
C2—C3 | 1.350 (3) | C2'—C3' | 1.354 (3) |
C2—C9 | 1.477 (3) | C2'—C9' | 1.483 (3) |
C3—C4 | 1.490 (3) | C3'—C4' | 1.487 (3) |
C3—C11 | 1.494 (3) | C3'—C11' | 1.494 (3) |
C4—C12 | 1.344 (3) | C4'—C12' | 1.340 (3) |
C4—C5 | 1.495 (3) | C4'—C5' | 1.495 (3) |
C5—C13 | 1.340 (3) | C5'—C13' | 1.334 (3) |
C5—C6 | 1.487 (3) | C5'—C6' | 1.485 (3) |
C6—C14 | 1.339 (3) | C6'—C14' | 1.338 (3) |
C7—H7A | 0.9800 | C7'—H7'1 | 0.9800 |
C7—H7B | 0.9800 | C7'—H7'2 | 0.9800 |
C7—H7C | 0.9800 | C7'—H7'3 | 0.9800 |
C8—H8A | 0.9800 | C8'—H8'1 | 0.9800 |
C8—H8B | 0.9800 | C8'—H8'2 | 0.9800 |
C8—H8C | 0.9800 | C8'—H8'3 | 0.9800 |
C9—C10 | 1.321 (4) | C9'—C10' | 1.328 (4) |
C9—H9 | 0.9500 | C9'—H9' | 0.9500 |
C10—C16 | 1.493 (4) | C10'—C16' | 1.495 (4) |
C10—C15 | 1.502 (4) | C10'—C15' | 1.507 (4) |
C11—C18 | 1.367 (4) | C11'—C18' | 1.362 (4) |
C11—C17 | 1.461 (4) | C11'—C17' | 1.463 (3) |
C12—C19 | 1.501 (3) | C12'—C20' | 1.501 (3) |
C12—C20 | 1.504 (3) | C12'—C19' | 1.509 (3) |
C13—C22 | 1.501 (3) | C13'—C22' | 1.507 (4) |
C13—C21 | 1.507 (4) | C13'—C21' | 1.507 (4) |
C14—C23 | 1.504 (3) | C14'—C23' | 1.507 (4) |
C14—C24 | 1.511 (3) | C14'—C24' | 1.517 (4) |
C15—H15A | 0.9800 | C15'—H15D | 0.9800 |
C15—H15B | 0.9800 | C15'—H15E | 0.9800 |
C15—H15C | 0.9800 | C15'—H15F | 0.9800 |
C16—H16A | 0.9800 | C16'—H16D | 0.9800 |
C16—H16B | 0.9800 | C16'—H16E | 0.9800 |
C16—H16C | 0.9800 | C16'—H16F | 0.9800 |
C17—H17A | 0.9800 | C17'—H17D | 0.9800 |
C17—H17B | 0.9800 | C17'—H17E | 0.9800 |
C17—H17C | 0.9800 | C17'—H17F | 0.9800 |
C18—H18A | 0.9500 | C18'—H18C | 0.9500 |
C18—H18B | 0.9500 | C18'—H18D | 0.9500 |
C19—H19A | 0.9800 | C19'—H19D | 0.9800 |
C19—H19B | 0.9800 | C19'—H19E | 0.9800 |
C19—H19C | 0.9800 | C19'—H19F | 0.9800 |
C20—H20A | 0.9800 | C20'—H20D | 0.9800 |
C20—H20B | 0.9800 | C20'—H20E | 0.9800 |
C20—H20C | 0.9800 | C20'—H20F | 0.9800 |
C21—H21A | 0.9800 | C21'—H21D | 0.9800 |
C21—H21B | 0.9800 | C21'—H21E | 0.9800 |
C21—H21C | 0.9800 | C21'—H21F | 0.9800 |
C22—H22A | 0.9800 | C22'—H22D | 0.9800 |
C22—H22B | 0.9800 | C22'—H22E | 0.9800 |
C22—H22C | 0.9800 | C22'—H22F | 0.9800 |
C23—H23A | 0.9800 | C23'—H23D | 0.9800 |
C23—H23B | 0.9800 | C23'—H23E | 0.9800 |
C23—H23C | 0.9800 | C23'—H23F | 0.9800 |
C24—H24A | 0.9800 | C24'—H24D | 0.9800 |
C24—H24B | 0.9800 | C24'—H24E | 0.9800 |
C24—H24C | 0.9800 | C24'—H24F | 0.9800 |
C8—C1—C2 | 109.31 (19) | C2'—C1'—C8' | 109.0 (2) |
C8—C1—C6 | 107.04 (19) | C2'—C1'—C7' | 105.22 (19) |
C2—C1—C6 | 112.08 (19) | C8'—C1'—C7' | 110.3 (2) |
C8—C1—C7 | 110.9 (2) | C2'—C1'—C6' | 112.14 (19) |
C2—C1—C7 | 105.07 (19) | C8'—C1'—C6' | 107.78 (19) |
C6—C1—C7 | 112.5 (2) | C7'—C1'—C6' | 112.3 (2) |
C3—C2—C9 | 122.9 (2) | C3'—C2'—C9' | 121.6 (2) |
C3—C2—C1 | 122.7 (2) | C3'—C2'—C1' | 122.9 (2) |
C9—C2—C1 | 114.3 (2) | C9'—C2'—C1' | 115.5 (2) |
C2—C3—C4 | 118.6 (2) | C2'—C3'—C4' | 118.7 (2) |
C2—C3—C11 | 122.6 (2) | C2'—C3'—C11' | 122.3 (2) |
C4—C3—C11 | 118.5 (2) | C4'—C3'—C11' | 118.8 (2) |
C12—C4—C3 | 126.8 (2) | C12'—C4'—C3' | 126.7 (2) |
C12—C4—C5 | 123.9 (2) | C12'—C4'—C5' | 123.9 (2) |
C3—C4—C5 | 109.21 (19) | C3'—C4'—C5' | 109.3 (2) |
C13—C5—C6 | 125.7 (2) | C13'—C5'—C6' | 125.1 (2) |
C13—C5—C4 | 123.8 (2) | C13'—C5'—C4' | 123.9 (2) |
C6—C5—C4 | 109.9 (2) | C6'—C5'—C4' | 110.3 (2) |
C14—C6—C5 | 122.0 (2) | C14'—C6'—C5' | 121.7 (2) |
C14—C6—C1 | 125.1 (2) | C14'—C6'—C1' | 125.8 (2) |
C5—C6—C1 | 112.90 (19) | C5'—C6'—C1' | 112.57 (19) |
C1—C7—H7A | 109.5 | C1'—C7'—H7'1 | 109.5 |
C1—C7—H7B | 109.5 | C1'—C7'—H7'2 | 109.5 |
H7A—C7—H7B | 109.5 | H7'1—C7'—H7'2 | 109.5 |
C1—C7—H7C | 109.5 | C1'—C7'—H7'3 | 109.5 |
H7A—C7—H7C | 109.5 | H7'1—C7'—H7'3 | 109.5 |
H7B—C7—H7C | 109.5 | H7'2—C7'—H7'3 | 109.5 |
C1—C8—H8A | 109.5 | C1'—C8'—H8'1 | 109.5 |
C1—C8—H8B | 109.5 | C1'—C8'—H8'2 | 109.5 |
H8A—C8—H8B | 109.5 | H8'1—C8'—H8'2 | 109.5 |
C1—C8—H8C | 109.5 | C1'—C8'—H8'3 | 109.5 |
H8A—C8—H8C | 109.5 | H8'1—C8'—H8'3 | 109.5 |
H8B—C8—H8C | 109.5 | H8'2—C8'—H8'3 | 109.5 |
C10—C9—C2 | 127.6 (2) | C10'—C9'—C2' | 126.8 (2) |
C10—C9—H9 | 116.2 | C10'—C9'—H9' | 116.6 |
C2—C9—H9 | 116.2 | C2'—C9'—H9' | 116.6 |
C9—C10—C16 | 124.2 (2) | C9'—C10'—C16' | 124.1 (3) |
C9—C10—C15 | 121.0 (3) | C9'—C10'—C15' | 121.2 (3) |
C16—C10—C15 | 114.8 (3) | C16'—C10'—C15' | 114.8 (3) |
C18—C11—C17 | 120.6 (2) | C18'—C11'—C17' | 121.1 (2) |
C18—C11—C3 | 120.0 (2) | C18'—C11'—C3' | 119.9 (2) |
C17—C11—C3 | 119.3 (2) | C17'—C11'—C3' | 119.0 (2) |
C4—C12—C19 | 124.8 (2) | C4'—C12'—C20' | 122.5 (2) |
C4—C12—C20 | 122.1 (2) | C4'—C12'—C19' | 124.9 (2) |
C19—C12—C20 | 113.1 (2) | C20'—C12'—C19' | 112.6 (2) |
C5—C13—C22 | 123.4 (2) | C5'—C13'—C22' | 123.7 (2) |
C5—C13—C21 | 122.8 (2) | C5'—C13'—C21' | 122.5 (2) |
C22—C13—C21 | 113.8 (2) | C22'—C13'—C21' | 113.7 (2) |
C6—C14—C23 | 123.1 (2) | C6'—C14'—C23' | 122.7 (2) |
C6—C14—C24 | 126.4 (2) | C6'—C14'—C24' | 126.7 (2) |
C23—C14—C24 | 110.5 (2) | C23'—C14'—C24' | 110.6 (2) |
C10—C15—H15A | 109.5 | C10'—C15'—H15D | 109.5 |
C10—C15—H15B | 109.5 | C10'—C15'—H15E | 109.5 |
H15A—C15—H15B | 109.5 | H15D—C15'—H15E | 109.5 |
C10—C15—H15C | 109.5 | C10'—C15'—H15F | 109.5 |
H15A—C15—H15C | 109.5 | H15D—C15'—H15F | 109.5 |
H15B—C15—H15C | 109.5 | H15E—C15'—H15F | 109.5 |
C10—C16—H16A | 109.5 | C10'—C16'—H16D | 109.5 |
C10—C16—H16B | 109.5 | C10'—C16'—H16E | 109.5 |
H16A—C16—H16B | 109.5 | H16D—C16'—H16E | 109.5 |
C10—C16—H16C | 109.5 | C10'—C16'—H16F | 109.5 |
H16A—C16—H16C | 109.5 | H16D—C16'—H16F | 109.5 |
H16B—C16—H16C | 109.5 | H16E—C16'—H16F | 109.5 |
C11—C17—H17A | 109.5 | C11'—C17'—H17D | 109.5 |
C11—C17—H17B | 109.5 | C11'—C17'—H17E | 109.5 |
H17A—C17—H17B | 109.5 | H17D—C17'—H17E | 109.5 |
C11—C17—H17C | 109.5 | C11'—C17'—H17F | 109.5 |
H17A—C17—H17C | 109.5 | H17D—C17'—H17F | 109.5 |
H17B—C17—H17C | 109.5 | H17E—C17'—H17F | 109.5 |
C11—C18—H18A | 120.0 | C11'—C18'—H18C | 120.0 |
C11—C18—H18B | 120.0 | C11'—C18'—H18D | 120.0 |
H18A—C18—H18B | 120.0 | H18C—C18'—H18D | 120.0 |
C12—C19—H19A | 109.5 | C12'—C19'—H19D | 109.5 |
C12—C19—H19B | 109.5 | C12'—C19'—H19E | 109.5 |
H19A—C19—H19B | 109.5 | H19D—C19'—H19E | 109.5 |
C12—C19—H19C | 109.5 | C12'—C19'—H19F | 109.5 |
H19A—C19—H19C | 109.5 | H19D—C19'—H19F | 109.5 |
H19B—C19—H19C | 109.5 | H19E—C19'—H19F | 109.5 |
C12—C20—H20A | 109.5 | C12'—C20'—H20D | 109.5 |
C12—C20—H20B | 109.5 | C12'—C20'—H20E | 109.5 |
H20A—C20—H20B | 109.5 | H20D—C20'—H20E | 109.5 |
C12—C20—H20C | 109.5 | C12'—C20'—H20F | 109.5 |
H20A—C20—H20C | 109.5 | H20D—C20'—H20F | 109.5 |
H20B—C20—H20C | 109.5 | H20E—C20'—H20F | 109.5 |
C13—C21—H21A | 109.5 | C13'—C21'—H21D | 109.5 |
C13—C21—H21B | 109.5 | C13'—C21'—H21E | 109.5 |
H21A—C21—H21B | 109.5 | H21D—C21'—H21E | 109.5 |
C13—C21—H21C | 109.5 | C13'—C21'—H21F | 109.5 |
H21A—C21—H21C | 109.5 | H21D—C21'—H21F | 109.5 |
H21B—C21—H21C | 109.5 | H21E—C21'—H21F | 109.5 |
C13—C22—H22A | 109.5 | C13'—C22'—H22D | 109.5 |
C13—C22—H22B | 109.5 | C13'—C22'—H22E | 109.5 |
H22A—C22—H22B | 109.5 | H22D—C22'—H22E | 109.5 |
C13—C22—H22C | 109.5 | C13'—C22'—H22F | 109.5 |
H22A—C22—H22C | 109.5 | H22D—C22'—H22F | 109.5 |
H22B—C22—H22C | 109.5 | H22E—C22'—H22F | 109.5 |
C14—C23—H23A | 109.5 | C14'—C23'—H23D | 109.5 |
C14—C23—H23B | 109.5 | C14'—C23'—H23E | 109.5 |
H23A—C23—H23B | 109.5 | H23D—C23'—H23E | 109.5 |
C14—C23—H23C | 109.5 | C14'—C23'—H23F | 109.5 |
H23A—C23—H23C | 109.5 | H23D—C23'—H23F | 109.5 |
H23B—C23—H23C | 109.5 | H23E—C23'—H23F | 109.5 |
C14—C24—H24A | 109.5 | C14'—C24'—H24D | 109.5 |
C14—C24—H24B | 109.5 | C14'—C24'—H24E | 109.5 |
H24A—C24—H24B | 109.5 | H24D—C24'—H24E | 109.5 |
C14—C24—H24C | 109.5 | C14'—C24'—H24F | 109.5 |
H24A—C24—H24C | 109.5 | H24D—C24'—H24F | 109.5 |
H24B—C24—H24C | 109.5 | H24E—C24'—H24F | 109.5 |
C8—C1—C2—C3 | −140.8 (2) | C8'—C1'—C2'—C3' | −140.6 (2) |
C6—C1—C2—C3 | −22.3 (3) | C7'—C1'—C2'—C3' | 101.1 (3) |
C7—C1—C2—C3 | 100.2 (3) | C6'—C1'—C2'—C3' | −21.3 (3) |
C8—C1—C2—C9 | 42.2 (3) | C8'—C1'—C2'—C9' | 42.4 (3) |
C6—C1—C2—C9 | 160.7 (2) | C7'—C1'—C2'—C9' | −75.9 (3) |
C7—C1—C2—C9 | −76.8 (2) | C6'—C1'—C2'—C9' | 161.7 (2) |
C9—C2—C3—C4 | −169.4 (2) | C9'—C2'—C3'—C4' | −169.8 (2) |
C1—C2—C3—C4 | 13.8 (3) | C1'—C2'—C3'—C4' | 13.3 (3) |
C9—C2—C3—C11 | 4.2 (4) | C9'—C2'—C3'—C11' | 4.4 (4) |
C1—C2—C3—C11 | −172.5 (2) | C1'—C2'—C3'—C11' | −172.5 (2) |
C2—C3—C4—C12 | −147.9 (2) | C2'—C3'—C4'—C12' | −147.5 (2) |
C11—C3—C4—C12 | 38.1 (3) | C11'—C3'—C4'—C12' | 38.2 (3) |
C2—C3—C4—C5 | 29.5 (3) | C2'—C3'—C4'—C5' | 29.2 (3) |
C11—C3—C4—C5 | −144.4 (2) | C11'—C3'—C4'—C5' | −145.2 (2) |
C12—C4—C5—C13 | −75.4 (3) | C12'—C4'—C5'—C13' | −76.0 (3) |
C3—C4—C5—C13 | 107.1 (3) | C3'—C4'—C5'—C13' | 107.3 (3) |
C12—C4—C5—C6 | 113.0 (3) | C12'—C4'—C5'—C6' | 112.5 (3) |
C3—C4—C5—C6 | −64.5 (2) | C3'—C4'—C5'—C6' | −64.2 (2) |
C13—C5—C6—C14 | 64.7 (3) | C13'—C5'—C6'—C14' | 64.9 (3) |
C4—C5—C6—C14 | −123.9 (2) | C4'—C5'—C6'—C14' | −123.7 (2) |
C13—C5—C6—C1 | −115.5 (3) | C13'—C5'—C6'—C1' | −115.4 (3) |
C4—C5—C6—C1 | 55.9 (3) | C4'—C5'—C6'—C1' | 56.0 (3) |
C8—C1—C6—C14 | −73.9 (3) | C2'—C1'—C6'—C14' | 165.5 (2) |
C2—C1—C6—C14 | 166.2 (2) | C8'—C1'—C6'—C14' | −74.5 (3) |
C7—C1—C6—C14 | 48.1 (3) | C7'—C1'—C6'—C14' | 47.2 (3) |
C8—C1—C6—C5 | 106.3 (2) | C2'—C1'—C6'—C5' | −14.2 (3) |
C2—C1—C6—C5 | −13.6 (3) | C8'—C1'—C6'—C5' | 105.8 (2) |
C7—C1—C6—C5 | −131.7 (2) | C7'—C1'—C6'—C5' | −132.4 (2) |
C3—C2—C9—C10 | 61.1 (4) | C3'—C2'—C9'—C10' | 61.6 (4) |
C1—C2—C9—C10 | −121.9 (3) | C1'—C2'—C9'—C10' | −121.4 (3) |
C2—C9—C10—C16 | −0.4 (5) | C2'—C9'—C10'—C16' | 1.9 (4) |
C2—C9—C10—C15 | 179.4 (3) | C2'—C9'—C10'—C15' | −177.5 (3) |
C2—C3—C11—C18 | −127.2 (3) | C2'—C3'—C11'—C18' | −126.4 (3) |
C4—C3—C11—C18 | 46.4 (3) | C4'—C3'—C11'—C18' | 47.7 (3) |
C2—C3—C11—C17 | 55.1 (3) | C2'—C3'—C11'—C17' | 56.3 (3) |
C4—C3—C11—C17 | −131.2 (3) | C4'—C3'—C11'—C17' | −129.5 (2) |
C3—C4—C12—C19 | 2.8 (4) | C3'—C4'—C12'—C20' | −178.9 (2) |
C5—C4—C12—C19 | −174.3 (2) | C5'—C4'—C12'—C20' | 4.9 (4) |
C3—C4—C12—C20 | −179.0 (2) | C3'—C4'—C12'—C19' | 2.3 (4) |
C5—C4—C12—C20 | 4.0 (4) | C5'—C4'—C12'—C19' | −173.9 (2) |
C6—C5—C13—C22 | −2.6 (4) | C6'—C5'—C13'—C22' | −3.6 (4) |
C4—C5—C13—C22 | −172.9 (2) | C4'—C5'—C13'—C22' | −173.8 (2) |
C6—C5—C13—C21 | 176.7 (2) | C6'—C5'—C13'—C21' | 176.7 (2) |
C4—C5—C13—C21 | 6.4 (4) | C4'—C5'—C13'—C21' | 6.5 (4) |
C5—C6—C14—C23 | 2.0 (4) | C5'—C6'—C14'—C23' | 3.8 (4) |
C1—C6—C14—C23 | −177.8 (2) | C1'—C6'—C14'—C23' | −175.8 (2) |
C5—C6—C14—C24 | −178.8 (2) | C5'—C6'—C14'—C24' | −177.5 (2) |
C1—C6—C14—C24 | 1.4 (4) | C1'—C6'—C14'—C24' | 2.9 (4) |
Experimental details
Crystal data | |
Chemical formula | C24H36 |
Mr | 324.53 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 143 |
a, b, c (Å) | 14.382 (2), 17.062 (2), 17.053 (2) |
β (°) | 95.436 (12) |
V (Å3) | 4165.6 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.06 |
Crystal size (mm) | 0.6 × 0.5 × 0.4 |
Data collection | |
Diffractometer | Stoe Stadi-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7622, 7330, 4782 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.165, 1.04 |
No. of reflections | 7330 |
No. of parameters | 455 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.27 |
Computer programs: DIF4 (Stoe & Cie, 1992), DIF4, REDU4 (Stoe & Cie, 1992), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1996), SHELXL97.
C2—C3 | 1.350 (3) | C2'—C3' | 1.354 (3) |
C4—C12 | 1.344 (3) | C4'—C12' | 1.340 (3) |
C5—C13 | 1.340 (3) | C5'—C13' | 1.334 (3) |
C6—C14 | 1.339 (3) | C6'—C14' | 1.338 (3) |
C9—C10 | 1.321 (4) | C9'—C10' | 1.328 (4) |
C11—C18 | 1.367 (4) | C11'—C18' | 1.362 (4) |
C2—C1—C6 | 112.08 (19) | C2'—C1'—C6' | 112.14 (19) |
C3—C2—C1 | 122.7 (2) | C3'—C2'—C1' | 122.9 (2) |
C2—C3—C4 | 118.6 (2) | C2'—C3'—C4' | 118.7 (2) |
C3—C4—C5 | 109.21 (19) | C3'—C4'—C5' | 109.3 (2) |
C6—C5—C4 | 109.9 (2) | C6'—C5'—C4' | 110.3 (2) |
C5—C6—C1 | 112.90 (19) | C5'—C6'—C1' | 112.57 (19) |
C6—C1—C2—C3 | −22.3 (3) | C6'—C1'—C2'—C3' | −21.3 (3) |
C1—C2—C3—C4 | 13.8 (3) | C1'—C2'—C3'—C4' | 13.3 (3) |
C2—C3—C4—C5 | 29.5 (3) | C2'—C3'—C4'—C5' | 29.2 (3) |
C3—C4—C5—C6 | −64.5 (2) | C3'—C4'—C5'—C6' | −64.2 (2) |
C4—C5—C6—C1 | 55.9 (3) | C4'—C5'—C6'—C1' | 56.0 (3) |
C2—C1—C6—C5 | −13.6 (3) | C2'—C1'—C6'—C5' | −14.2 (3) |
Permethylbutatriene, (1), generated in situ, is known to cyclooligomerize to dodecamethyl[6]radialene, (2), in the presence of nickel catalyst systems (Iyoda et al., 1984, 1988; Stehling & Wilke, 1985). Although the yield of this process is good (>70%), it is accompanied by the formation of several by-products, most of which have not been fully characterized. Repeating this trimerization (Höpfner, 1996), we have isolated one of the minor (5%) products and have identified it as the title compound, (3), by X-ray methods.
Compound (3) crystallizes with two independent but closely similar molecules (Fig. 1); a least-squares fit of all non-H atoms (Fig. 2) gave an r.m.s. deviation of only 0.04 Å. For this reason, only the dimensions of molecule 1 (unprimed atoms) will be discussed explicitly.
The ring shows a torsion angle of 13.8 (3)° about the C2═C3 double bond. The sp2 angles at the radialene-type ring junctions are markedly narrowed, with ring angles of 109.2 (2), 109.9 (2) and 112.9 (2)° at C4, C5 and C6, respectively. Other molecular dimensions may be regarded as normal (e.g. the double-bond lengths in Table 1), but considering the caveat given in the Experimental section.