(5RS,10SR,15RS)-Trimethyl-truxene.

The title mol-ecule, C(30)H(24), was prepared as a possible precursor to buckminsterfullerene cages. The two enanti-omers 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

C30H24

M = 384.49

Monoclinic,

a = 8.6755 (2) Å

b = 18.2860 (4) Å

c = 12.8206 (3) Å

β = 96.007 (1)°

V = 2022.69 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 90 K

0.15 × 0.15 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.955, T max = 0.976

13386 measured reflections

7338 independent reflections

5008 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.157

S = 1.04

7338 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048616/qm2041sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048616/qm2041Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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	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

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)