organic compounds
(5RS,10SR,15RS)-Trimethyltruxene1
aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
*Correspondence e-mail: ffroncz@lsu.edu
The title molecule, C30H24, was prepared as a possible precursor to buckminsterfullerene cages. The two enantiomers adopt the anti configuration, with one S/R and two R/S methyl groups, one anti to the other two. The truxene framework is slightly non-planar: with respect to the central six-ring mean plane, the three methyl C atoms are 1.377 (3), −1.475 (3) and 1.515 (3) Å distant, whereas the respective proximate peripheral six-ring mean planes make dihedral angles of 6.27 (6), 3.45 (7) and −7.37 (7)°.
Related literature
For related structures, see: De Frutos et al. (1999, 2002). For the synthesis of truxenes, see: Amick & Scott (2007); Dehmlow & Kelle (1997); Kipping (1894a,b); Hausmann (1889); Wislicenus (1887). For buckminsterfullerene, see: Kroto et al. (1985). Buckybowls are intermediates in the synthesis of buckminsterfullerene. Truxene compounds, which serve as backbone of bucky bowl derivatives, have been fabricated for use as star-shaped organic semiconductors in solution, see: Sun et al. (2005).
Experimental
Crystal data
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Data collection: COLLECT (Nonius, 2000); cell SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
https://doi.org/10.1107/S1600536811048616/qm2041sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048616/qm2041Isup2.hkl
Synthesis of truxene was carried by the one-pot, acid catalyzed, head-to-tail cyclotrimerization synthesis method detailed in (Amick & Scott, 2007) The trimethylation of truxene was carried out by treating truxene with n-butyl lithium, followed by treatment with methyl iodide. A suitable single-crystal was obtained by recrystallization from diethyl ether, dichloromethane and methanol.
All H atoms were placed in calculated positions, guided by difference maps, with C—H bond distances 0.95 (aromatic C), 1.00 (alkyl C) Å, and Uiso=1.2Ueq, thereafter refined as riding. A torsional parameter was refined for each methyl group, with C—H bond distances 0.98 Å and Uiso = 1.5Ueq. The largest peak in the final difference map was at the center of the C18–C26 bond, and the top 33 peaks lay near bond centers.
Buckminsterfullerene is a spherical fullerene molecule with the formula C60. It was first prepared in 1985 by Kroto et al. Buckybowls have been recognized as valuable intermediates in the synthesis of buckminsterfullerene and also show many valuable and interesting properties, including surface selective chemistry. As a part of ongoing investigations for synthesis of bucky bowls, the title molecule, trimethyltruxene, C30H24, was prepared as a possible precursor to buckminsterfullerene cages. Furthermore, these truxene compounds, which serve as backbone of bucky bowl derivatives also have shown properties of organic field-effect transistors (OFETs) based on oligothiophene-functionalized truxene derivatives, which have been fabricated for use as novel star-shaped organic semiconductors in solution (Sun et al., 2005).
Two isomers of the title compound, syn and anti are possible. De Frutos et al. (2002) prepared mixtures of the two isomers, which could be converted to the pure, more stable syn compound by reaction with base, potassium t-butoxide. We report here the structure of the less stable anti isomer, which is not a viable precursor for buckybowls.
The parent heptacyclic aromatic system, truxene (10,15-dihydro-5H-diindeno[1,2 - a:1',2'-c]fluorene), is planar with 3/m (C3 h) symmetry. The title molecule, I, is slightly non-planar with no discernable pattern: with respect to the central 6-ring mean plane, the three methyl groups are +1.377 (3), -1.475 (3) and +1.515 (3) Å distant, whereas the proximate peripheral 6-ring mean planes make dihedral angles of +6.27 (6)°, +3.45 (7)° and -7.37 (7)°.
For related structures, see: De Frutos et al. (1999, 2002). For the synthesis of truxenes, see: Amick & Scott (2007); Dehmlow & Kelle (1997); Kipping (1894a,b); Hausmann (1889); Wislicenus (1887). For buckminsterfullerene, see: Kroto et al. (1985). Buckybowls are intermediates in the synthesis of buckminsterfullerene. Truxene compounds, which serve as backbone of bucky bowl derivatives, have been fabricated for use as novel star-shaped organic semiconductors in solution, see:Sun et al. (2005).
Data collection: COLLECT (Nonius, 2000); cell
SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).C30H24 | F(000) = 816 |
Mr = 384.49 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6571 reflections |
a = 8.6755 (2) Å | θ = 2.5–33.5° |
b = 18.2860 (4) Å | µ = 0.07 mm−1 |
c = 12.8206 (3) Å | T = 90 K |
β = 96.007 (1)° | Prism, yellow |
V = 2022.69 (8) Å3 | 0.15 × 0.15 × 0.13 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 7338 independent reflections |
Radiation source: sealed tube | 5008 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 9 pixels mm-1 | θmax = 33.5°, θmin = 2.6° |
CCD rotation images, thick slices scans | h = −13→13 |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | k = −28→23 |
Tmin = 0.955, Tmax = 0.976 | l = −19→19 |
13386 measured reflections |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0893P)2 + 0.0548P] where P = (Fo2 + 2Fc2)/3 |
7338 reflections | (Δ/σ)max = 0.001 |
274 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
0 constraints |
C30H24 | V = 2022.69 (8) Å3 |
Mr = 384.49 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.6755 (2) Å | µ = 0.07 mm−1 |
b = 18.2860 (4) Å | T = 90 K |
c = 12.8206 (3) Å | 0.15 × 0.15 × 0.13 mm |
β = 96.007 (1)° |
Nonius KappaCCD diffractometer | 7338 independent reflections |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | 5008 reflections with I > 2σ(I) |
Tmin = 0.955, Tmax = 0.976 | Rint = 0.034 |
13386 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.48 e Å−3 |
7338 reflections | Δρmin = −0.29 e Å−3 |
274 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. |
x | y | z | Uiso*/Ueq | ||
C01 | −0.07933 (13) | 0.09157 (6) | 0.49364 (9) | 0.0170 (2) | |
H01 | −0.0475 | 0.0572 | 0.5526 | 0.020* | |
C02 | −0.19146 (13) | 0.05432 (6) | 0.41175 (10) | 0.0174 (2) | |
C03 | −0.33977 (14) | 0.02847 (7) | 0.42222 (10) | 0.0203 (2) | |
H03 | −0.3798 | 0.0296 | 0.4884 | 0.024* | |
C04 | −0.42872 (14) | 0.00091 (7) | 0.33434 (10) | 0.0206 (2) | |
H04 | −0.5294 | −0.0178 | 0.3409 | 0.025* | |
C05 | −0.37157 (14) | 0.00050 (7) | 0.23706 (10) | 0.0192 (2) | |
H05 | −0.4346 | −0.0173 | 0.1774 | 0.023* | |
C06 | −0.22251 (13) | 0.02602 (6) | 0.22615 (10) | 0.0177 (2) | |
H06 | −0.1835 | 0.0254 | 0.1596 | 0.021* | |
C07 | −0.13174 (13) | 0.05235 (6) | 0.31430 (9) | 0.0154 (2) | |
C08 | 0.02504 (13) | 0.08458 (6) | 0.32688 (9) | 0.0153 (2) | |
C09 | 0.13369 (13) | 0.09525 (6) | 0.25572 (9) | 0.0152 (2) | |
C10 | 0.13230 (13) | 0.06937 (6) | 0.14305 (9) | 0.0172 (2) | |
H10 | 0.0400 | 0.0894 | 0.0990 | 0.021* | |
C11 | 0.28051 (14) | 0.10304 (6) | 0.11113 (10) | 0.0174 (2) | |
C12 | 0.34197 (15) | 0.09751 (7) | 0.01588 (10) | 0.0213 (3) | |
H12 | 0.2860 | 0.0734 | −0.0418 | 0.026* | |
C13 | 0.48723 (15) | 0.12793 (7) | 0.00611 (10) | 0.0223 (3) | |
H13 | 0.5300 | 0.1249 | −0.0590 | 0.027* | |
C14 | 0.57001 (14) | 0.16264 (6) | 0.09067 (10) | 0.0197 (2) | |
H14 | 0.6696 | 0.1823 | 0.0832 | 0.024* | |
C15 | 0.50823 (14) | 0.16888 (6) | 0.18647 (10) | 0.0182 (2) | |
H15 | 0.5647 | 0.1928 | 0.2441 | 0.022* | |
C16 | 0.36210 (13) | 0.13934 (6) | 0.19621 (9) | 0.0154 (2) | |
C17 | 0.27069 (13) | 0.13486 (6) | 0.28678 (9) | 0.0149 (2) | |
C18 | 0.30010 (12) | 0.16021 (6) | 0.38920 (9) | 0.0148 (2) | |
C19 | 0.43313 (13) | 0.20650 (6) | 0.43845 (9) | 0.0165 (2) | |
H19 | 0.5346 | 0.1829 | 0.4286 | 0.020* | |
C20 | 0.40577 (13) | 0.20572 (6) | 0.55330 (9) | 0.0162 (2) | |
C21 | 0.49513 (13) | 0.23644 (7) | 0.63774 (10) | 0.0191 (2) | |
H21 | 0.5885 | 0.2614 | 0.6278 | 0.023* | |
C22 | 0.44625 (14) | 0.23020 (7) | 0.73774 (10) | 0.0204 (2) | |
H22 | 0.5061 | 0.2515 | 0.7962 | 0.025* | |
C23 | 0.30980 (14) | 0.19282 (7) | 0.75213 (10) | 0.0197 (2) | |
H23 | 0.2784 | 0.1884 | 0.8206 | 0.024* | |
C24 | 0.21912 (13) | 0.16198 (6) | 0.66747 (9) | 0.0178 (2) | |
H24 | 0.1268 | 0.1363 | 0.6779 | 0.021* | |
C25 | 0.26576 (13) | 0.16933 (6) | 0.56710 (9) | 0.0153 (2) | |
C26 | 0.19633 (13) | 0.14324 (6) | 0.46379 (9) | 0.0148 (2) | |
C27 | 0.05726 (13) | 0.10782 (6) | 0.43211 (9) | 0.0149 (2) | |
C28 | −0.15190 (14) | 0.16121 (7) | 0.53548 (11) | 0.0226 (3) | |
H28A | −0.0753 | 0.1860 | 0.5849 | 0.034* | |
H28B | −0.2422 | 0.1479 | 0.5714 | 0.034* | |
H28C | −0.1843 | 0.1940 | 0.4768 | 0.034* | |
C29 | 0.13709 (15) | −0.01460 (7) | 0.13416 (11) | 0.0230 (3) | |
H29A | 0.1441 | −0.0285 | 0.0610 | 0.034* | |
H29B | 0.0425 | −0.0354 | 0.1578 | 0.034* | |
H29C | 0.2277 | −0.0334 | 0.1781 | 0.034* | |
C30 | 0.42829 (15) | 0.28518 (7) | 0.39498 (10) | 0.0223 (3) | |
H30A | 0.4338 | 0.2838 | 0.3190 | 0.033* | |
H30B | 0.5166 | 0.3129 | 0.4286 | 0.033* | |
H30C | 0.3315 | 0.3088 | 0.4097 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C01 | 0.0155 (5) | 0.0216 (5) | 0.0142 (5) | −0.0022 (4) | 0.0025 (4) | 0.0001 (4) |
C02 | 0.0162 (5) | 0.0190 (5) | 0.0171 (6) | −0.0013 (4) | 0.0021 (4) | 0.0002 (4) |
C03 | 0.0189 (5) | 0.0244 (6) | 0.0184 (6) | −0.0038 (5) | 0.0051 (5) | −0.0007 (5) |
C04 | 0.0163 (5) | 0.0235 (6) | 0.0224 (6) | −0.0043 (5) | 0.0036 (5) | −0.0006 (5) |
C05 | 0.0167 (5) | 0.0208 (6) | 0.0196 (6) | −0.0017 (4) | −0.0004 (4) | −0.0024 (5) |
C06 | 0.0165 (5) | 0.0205 (5) | 0.0162 (6) | −0.0013 (4) | 0.0016 (4) | −0.0009 (4) |
C07 | 0.0137 (5) | 0.0161 (5) | 0.0164 (5) | −0.0005 (4) | 0.0022 (4) | −0.0001 (4) |
C08 | 0.0144 (5) | 0.0170 (5) | 0.0143 (5) | −0.0010 (4) | 0.0007 (4) | −0.0001 (4) |
C09 | 0.0147 (5) | 0.0172 (5) | 0.0139 (5) | 0.0002 (4) | 0.0019 (4) | 0.0004 (4) |
C10 | 0.0160 (5) | 0.0215 (5) | 0.0143 (5) | −0.0022 (4) | 0.0023 (4) | −0.0018 (4) |
C11 | 0.0177 (5) | 0.0193 (5) | 0.0155 (5) | −0.0012 (4) | 0.0035 (4) | −0.0004 (4) |
C12 | 0.0229 (6) | 0.0254 (6) | 0.0156 (6) | −0.0037 (5) | 0.0026 (5) | −0.0035 (5) |
C13 | 0.0246 (6) | 0.0269 (6) | 0.0168 (6) | −0.0022 (5) | 0.0080 (5) | −0.0001 (5) |
C14 | 0.0190 (5) | 0.0197 (5) | 0.0214 (6) | −0.0024 (4) | 0.0065 (5) | 0.0001 (5) |
C15 | 0.0174 (5) | 0.0193 (5) | 0.0183 (6) | −0.0018 (4) | 0.0032 (4) | −0.0004 (4) |
C16 | 0.0158 (5) | 0.0166 (5) | 0.0142 (5) | 0.0005 (4) | 0.0033 (4) | 0.0003 (4) |
C17 | 0.0141 (5) | 0.0165 (5) | 0.0143 (5) | 0.0007 (4) | 0.0019 (4) | 0.0007 (4) |
C18 | 0.0132 (5) | 0.0163 (5) | 0.0147 (5) | 0.0004 (4) | 0.0007 (4) | −0.0002 (4) |
C19 | 0.0147 (5) | 0.0197 (5) | 0.0153 (5) | −0.0012 (4) | 0.0021 (4) | −0.0024 (4) |
C20 | 0.0157 (5) | 0.0172 (5) | 0.0154 (5) | 0.0017 (4) | 0.0003 (4) | −0.0013 (4) |
C21 | 0.0169 (5) | 0.0207 (5) | 0.0197 (6) | −0.0020 (5) | 0.0012 (4) | −0.0040 (5) |
C22 | 0.0212 (6) | 0.0226 (6) | 0.0169 (6) | −0.0003 (5) | −0.0013 (5) | −0.0046 (5) |
C23 | 0.0221 (6) | 0.0228 (6) | 0.0139 (6) | 0.0024 (5) | 0.0011 (4) | 0.0003 (4) |
C24 | 0.0173 (5) | 0.0205 (5) | 0.0155 (6) | 0.0001 (4) | 0.0018 (4) | 0.0004 (4) |
C25 | 0.0153 (5) | 0.0159 (5) | 0.0144 (5) | 0.0016 (4) | 0.0002 (4) | −0.0004 (4) |
C26 | 0.0147 (5) | 0.0161 (5) | 0.0134 (5) | 0.0014 (4) | 0.0011 (4) | −0.0002 (4) |
C27 | 0.0146 (5) | 0.0169 (5) | 0.0132 (5) | 0.0000 (4) | 0.0019 (4) | 0.0006 (4) |
C28 | 0.0165 (5) | 0.0283 (6) | 0.0230 (6) | −0.0009 (5) | 0.0023 (5) | −0.0062 (5) |
C29 | 0.0229 (6) | 0.0226 (6) | 0.0240 (7) | −0.0045 (5) | 0.0055 (5) | −0.0057 (5) |
C30 | 0.0254 (6) | 0.0201 (6) | 0.0218 (6) | −0.0035 (5) | 0.0046 (5) | −0.0013 (5) |
C01—C02 | 1.5161 (17) | C15—C16 | 1.3956 (16) |
C01—C27 | 1.5201 (15) | C15—H15 | 0.9500 |
C01—C28 | 1.5416 (17) | C16—C17 | 1.4754 (15) |
C01—H01 | 1.0000 | C17—C18 | 1.3906 (16) |
C02—C03 | 1.3904 (16) | C18—C26 | 1.4148 (15) |
C02—C07 | 1.4021 (16) | C18—C19 | 1.5148 (16) |
C03—C04 | 1.3917 (18) | C19—C20 | 1.5159 (16) |
C03—H03 | 0.9500 | C19—C30 | 1.5419 (17) |
C04—C05 | 1.3895 (17) | C19—H19 | 1.0000 |
C04—H04 | 0.9500 | C20—C21 | 1.3831 (16) |
C05—C06 | 1.3955 (16) | C20—C25 | 1.4123 (16) |
C05—H05 | 0.9500 | C21—C22 | 1.3966 (17) |
C06—C07 | 1.3939 (17) | C21—H21 | 0.9500 |
C06—H06 | 0.9500 | C22—C23 | 1.3958 (17) |
C07—C08 | 1.4756 (15) | C22—H22 | 0.9500 |
C08—C09 | 1.3924 (15) | C23—C24 | 1.3915 (17) |
C08—C27 | 1.4142 (16) | C23—H23 | 0.9500 |
C09—C17 | 1.4131 (16) | C24—C25 | 1.3952 (16) |
C09—C10 | 1.5188 (16) | C24—H24 | 0.9500 |
C10—C11 | 1.5199 (16) | C25—C26 | 1.4756 (16) |
C10—C29 | 1.5405 (17) | C26—C27 | 1.3919 (16) |
C10—H10 | 1.0000 | C28—H28A | 0.9800 |
C11—C12 | 1.3864 (16) | C28—H28B | 0.9800 |
C11—C16 | 1.4035 (17) | C28—H28C | 0.9800 |
C12—C13 | 1.3950 (17) | C29—H29A | 0.9800 |
C12—H12 | 0.9500 | C29—H29B | 0.9800 |
C13—C14 | 1.3896 (18) | C29—H29C | 0.9800 |
C13—H13 | 0.9500 | C30—H30A | 0.9800 |
C14—C15 | 1.3951 (16) | C30—H30B | 0.9800 |
C14—H14 | 0.9500 | C30—H30C | 0.9800 |
C02—C01—C27 | 101.95 (9) | C18—C17—C09 | 120.18 (10) |
C02—C01—C28 | 110.87 (9) | C18—C17—C16 | 131.61 (10) |
C27—C01—C28 | 112.83 (10) | C09—C17—C16 | 108.19 (10) |
C02—C01—H01 | 110.3 | C17—C18—C26 | 119.89 (10) |
C27—C01—H01 | 110.3 | C17—C18—C19 | 129.52 (10) |
C28—C01—H01 | 110.3 | C26—C18—C19 | 110.59 (10) |
C03—C02—C07 | 120.61 (11) | C18—C19—C20 | 102.11 (9) |
C03—C02—C01 | 128.25 (11) | C18—C19—C30 | 112.34 (10) |
C07—C02—C01 | 111.01 (10) | C20—C19—C30 | 111.02 (10) |
C02—C03—C04 | 119.03 (11) | C18—C19—H19 | 110.4 |
C02—C03—H03 | 120.5 | C20—C19—H19 | 110.4 |
C04—C03—H03 | 120.5 | C30—C19—H19 | 110.4 |
C05—C04—C03 | 120.59 (11) | C21—C20—C25 | 120.82 (11) |
C05—C04—H04 | 119.7 | C21—C20—C19 | 128.64 (10) |
C03—C04—H04 | 119.7 | C25—C20—C19 | 110.51 (10) |
C04—C05—C06 | 120.64 (12) | C20—C21—C22 | 119.09 (11) |
C04—C05—H05 | 119.7 | C20—C21—H21 | 120.5 |
C06—C05—H05 | 119.7 | C22—C21—H21 | 120.5 |
C07—C06—C05 | 119.01 (11) | C23—C22—C21 | 120.30 (11) |
C07—C06—H06 | 120.5 | C23—C22—H22 | 119.8 |
C05—C06—H06 | 120.5 | C21—C22—H22 | 119.8 |
C06—C07—C02 | 120.09 (10) | C24—C23—C22 | 120.90 (11) |
C06—C07—C08 | 131.50 (11) | C24—C23—H23 | 119.6 |
C02—C07—C08 | 108.34 (10) | C22—C23—H23 | 119.6 |
C09—C08—C27 | 120.21 (10) | C23—C24—C25 | 119.04 (11) |
C09—C08—C07 | 131.59 (11) | C23—C24—H24 | 120.5 |
C27—C08—C07 | 108.19 (10) | C25—C24—H24 | 120.5 |
C08—C09—C17 | 119.62 (11) | C24—C25—C20 | 119.81 (11) |
C08—C09—C10 | 129.86 (10) | C24—C25—C26 | 131.77 (10) |
C17—C09—C10 | 110.52 (9) | C20—C25—C26 | 108.39 (10) |
C09—C10—C11 | 101.95 (9) | C27—C26—C18 | 119.88 (10) |
C09—C10—C29 | 112.54 (10) | C27—C26—C25 | 132.24 (10) |
C11—C10—C29 | 110.72 (9) | C18—C26—C25 | 107.88 (10) |
C09—C10—H10 | 110.5 | C26—C27—C08 | 119.80 (10) |
C11—C10—H10 | 110.5 | C26—C27—C01 | 129.68 (10) |
C29—C10—H10 | 110.5 | C08—C27—C01 | 110.44 (10) |
C12—C11—C16 | 120.66 (11) | C01—C28—H28A | 109.5 |
C12—C11—C10 | 128.45 (11) | C01—C28—H28B | 109.5 |
C16—C11—C10 | 110.75 (10) | H28A—C28—H28B | 109.5 |
C11—C12—C13 | 118.97 (12) | C01—C28—H28C | 109.5 |
C11—C12—H12 | 120.5 | H28A—C28—H28C | 109.5 |
C13—C12—H12 | 120.5 | H28B—C28—H28C | 109.5 |
C14—C13—C12 | 120.66 (11) | C10—C29—H29A | 109.5 |
C14—C13—H13 | 119.7 | C10—C29—H29B | 109.5 |
C12—C13—H13 | 119.7 | H29A—C29—H29B | 109.5 |
C13—C14—C15 | 120.62 (11) | C10—C29—H29C | 109.5 |
C13—C14—H14 | 119.7 | H29A—C29—H29C | 109.5 |
C15—C14—H14 | 119.7 | H29B—C29—H29C | 109.5 |
C14—C15—C16 | 118.91 (11) | C19—C30—H30A | 109.5 |
C14—C15—H15 | 120.5 | C19—C30—H30B | 109.5 |
C16—C15—H15 | 120.5 | H30A—C30—H30B | 109.5 |
C15—C16—C11 | 120.16 (11) | C19—C30—H30C | 109.5 |
C15—C16—C17 | 131.30 (11) | H30A—C30—H30C | 109.5 |
C11—C16—C17 | 108.46 (10) | H30B—C30—H30C | 109.5 |
C27—C01—C02—C03 | −178.33 (12) | C11—C16—C17—C18 | 178.54 (12) |
C28—C01—C02—C03 | −57.99 (16) | C15—C16—C17—C09 | −176.37 (12) |
C27—C01—C02—C07 | −2.60 (12) | C11—C16—C17—C09 | 0.28 (13) |
C28—C01—C02—C07 | 117.74 (11) | C09—C17—C18—C26 | 3.09 (16) |
C07—C02—C03—C04 | −0.37 (18) | C16—C17—C18—C26 | −174.99 (11) |
C01—C02—C03—C04 | 175.00 (11) | C09—C17—C18—C19 | −176.57 (11) |
C02—C03—C04—C05 | −1.24 (18) | C16—C17—C18—C19 | 5.3 (2) |
C03—C04—C05—C06 | 1.61 (19) | C17—C18—C19—C20 | −173.01 (11) |
C04—C05—C06—C07 | −0.33 (18) | C26—C18—C19—C20 | 7.30 (12) |
C05—C06—C07—C02 | −1.26 (17) | C17—C18—C19—C30 | 67.99 (15) |
C05—C06—C07—C08 | −177.68 (11) | C26—C18—C19—C30 | −111.70 (11) |
C03—C02—C07—C06 | 1.63 (18) | C18—C19—C20—C21 | 176.85 (11) |
C01—C02—C07—C06 | −174.48 (10) | C30—C19—C20—C21 | −63.23 (16) |
C03—C02—C07—C08 | 178.80 (11) | C18—C19—C20—C25 | −5.03 (12) |
C01—C02—C07—C08 | 2.70 (13) | C30—C19—C20—C25 | 114.90 (11) |
C06—C07—C08—C09 | −3.7 (2) | C25—C20—C21—C22 | 0.88 (17) |
C02—C07—C08—C09 | 179.52 (12) | C19—C20—C21—C22 | 178.83 (11) |
C06—C07—C08—C27 | 175.11 (12) | C20—C21—C22—C23 | 0.61 (18) |
C02—C07—C08—C27 | −1.63 (13) | C21—C22—C23—C24 | −0.82 (18) |
C27—C08—C09—C17 | −5.30 (17) | C22—C23—C24—C25 | −0.48 (18) |
C07—C08—C09—C17 | 173.44 (11) | C23—C24—C25—C20 | 1.95 (17) |
C27—C08—C09—C10 | 173.82 (11) | C23—C24—C25—C26 | 179.84 (12) |
C07—C08—C09—C10 | −7.4 (2) | C21—C20—C25—C24 | −2.18 (17) |
C08—C09—C10—C11 | 177.42 (12) | C19—C20—C25—C24 | 179.53 (10) |
C17—C09—C10—C11 | −3.40 (12) | C21—C20—C25—C26 | 179.47 (10) |
C08—C09—C10—C29 | −63.93 (16) | C19—C20—C25—C26 | 1.18 (12) |
C17—C09—C10—C29 | 115.25 (11) | C17—C18—C26—C27 | −6.66 (16) |
C09—C10—C11—C12 | 179.26 (12) | C19—C18—C26—C27 | 173.06 (10) |
C29—C10—C11—C12 | 59.33 (17) | C17—C18—C26—C25 | 173.32 (10) |
C09—C10—C11—C16 | 3.59 (13) | C19—C18—C26—C25 | −6.95 (12) |
C29—C10—C11—C16 | −116.35 (11) | C24—C25—C26—C27 | 5.5 (2) |
C16—C11—C12—C13 | 0.69 (18) | C20—C25—C26—C27 | −176.45 (12) |
C10—C11—C12—C13 | −174.61 (12) | C24—C25—C26—C18 | −174.51 (12) |
C11—C12—C13—C14 | 0.63 (19) | C20—C25—C26—C18 | 3.56 (12) |
C12—C13—C14—C15 | −1.14 (19) | C18—C26—C27—C08 | 4.24 (16) |
C13—C14—C15—C16 | 0.32 (18) | C25—C26—C27—C08 | −175.74 (11) |
C14—C15—C16—C11 | 1.00 (17) | C18—C26—C27—C01 | −172.36 (11) |
C14—C15—C16—C17 | 177.32 (11) | C25—C26—C27—C01 | 7.7 (2) |
C12—C11—C16—C15 | −1.52 (18) | C09—C08—C27—C26 | 1.74 (17) |
C10—C11—C16—C15 | 174.55 (10) | C07—C08—C27—C26 | −177.27 (10) |
C12—C11—C16—C17 | −178.61 (11) | C09—C08—C27—C01 | 178.95 (10) |
C10—C11—C16—C17 | −2.54 (13) | C07—C08—C27—C01 | −0.06 (13) |
C08—C09—C17—C18 | 2.87 (17) | C02—C01—C27—C26 | 178.41 (11) |
C10—C09—C17—C18 | −176.40 (10) | C28—C01—C27—C26 | 59.45 (16) |
C08—C09—C17—C16 | −178.63 (10) | C02—C01—C27—C08 | 1.55 (12) |
C10—C09—C17—C16 | 2.09 (13) | C28—C01—C27—C08 | −117.41 (11) |
C15—C16—C17—C18 | 1.9 (2) |
Experimental details
Crystal data | |
Chemical formula | C30H24 |
Mr | 384.49 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 90 |
a, b, c (Å) | 8.6755 (2), 18.2860 (4), 12.8206 (3) |
β (°) | 96.007 (1) |
V (Å3) | 2022.69 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.15 × 0.15 × 0.13 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | Multi-scan (SCALEPACK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.955, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13386, 7338, 5008 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.777 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.157, 1.04 |
No. of reflections | 7338 |
No. of parameters | 274 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.29 |
Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Footnotes
1CAS 478358-72-4.
Acknowledgements
The purchase of the diffractometer was made possible by grant No. LEQSF(1999–1200)-ENH-TR-13, administered by the Louisiana Board of Regents.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Buckminsterfullerene is a spherical fullerene molecule with the formula C60. It was first prepared in 1985 by Kroto et al. Buckybowls have been recognized as valuable intermediates in the synthesis of buckminsterfullerene and also show many valuable and interesting properties, including surface selective chemistry. As a part of ongoing investigations for synthesis of bucky bowls, the title molecule, trimethyltruxene, C30H24, was prepared as a possible precursor to buckminsterfullerene cages. Furthermore, these truxene compounds, which serve as backbone of bucky bowl derivatives also have shown properties of organic field-effect transistors (OFETs) based on oligothiophene-functionalized truxene derivatives, which have been fabricated for use as novel star-shaped organic semiconductors in solution (Sun et al., 2005).
Two isomers of the title compound, syn and anti are possible. De Frutos et al. (2002) prepared mixtures of the two isomers, which could be converted to the pure, more stable syn compound by reaction with base, potassium t-butoxide. We report here the structure of the less stable anti isomer, which is not a viable precursor for buckybowls.
The parent heptacyclic aromatic system, truxene (10,15-dihydro-5H-diindeno[1,2 - a:1',2'-c]fluorene), is planar with 3/m (C3 h) symmetry. The title molecule, I, is slightly non-planar with no discernable pattern: with respect to the central 6-ring mean plane, the three methyl groups are +1.377 (3), -1.475 (3) and +1.515 (3) Å distant, whereas the proximate peripheral 6-ring mean planes make dihedral angles of +6.27 (6)°, +3.45 (7)° and -7.37 (7)°.