organic papers
Acta Cryst.(2006). E62, o777–o779 doi:10.1107/S160053680600256X Liet al. C
27H24
o777
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
1,3,5-Tris(4-methylphenyl)benzene
Zhong-Shui Li, Jian-Xin Chen,* Yuan-Biao Huang, Gu-Rong Chen and Ting-Yan Lan
College of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian 350007, People’s Republic of China
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 293 K
Mean(C–C) = 0.003 A˚ Rfactor = 0.054 wRfactor = 0.102
Data-to-parameter ratio = 18.9
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 3 January 2006 Accepted 20 January 2006
#2006 International Union of Crystallography All rights reserved
The title compound, C27H24, with a propeller-like shape,
crystallizes with two crystallographically independent mol-ecules in the asymmetric unit. Intermolecular–interactions are pronounced in the crystal structure.
Comment
Numerous small molecular propellers of approximate D3
symmetry are known, but the vast majority of these compounds have the structure (aryl)3X, where Xis a single
atom (Tonget al., 1997). However, we present the structure of (I) where the central atom is replaced by a benzene ring (Weberet al., 1988; Thallapallyet al., 2000; Elmorsyet al., 1991; Grilliet al., 2002; Lindemanet al., 1984).
The crystal stucture of the title compound, (I), has two molecules (1 and 2) in the asymmetric unit (Fig. 1). Selected geometric parameters are shown in Table 1. In molecule 1, the central aromatic ring 1 (atoms C1–C6) is tilted with respect to thep-methylphenyl rings 2 (atoms C19–C24), 3 (C7–C12) and 4 (C13–C18), with dihedral angles of 42.93 (6), 35.15 (7) and 39.95 (8), respectively. In molecule 2, the dihedral angles of
ring 10 (atoms C28–C33) with rings 20 (atoms C46–C51), 30
(C34–C39) and 40 (C40–C45) are 40.38 (8), 34.48 (7) and
47.99 (7), respectively.p-Methylphenyl ring 4 in molecule 1 is close to being perpendicular to ring 40in molecule 2, with a dihedral angle of 88.08 (6). However, rings 1, 2 and 3 are
approximately parallel to the corresponding rings 10, 20and 30
centroid–centroid distances of 3.46–3.64 A˚ ) support the crystal packing (Fig. 2).
Experimental
All reagents were of AR grade, available commercially and used without further purification. The title compound was prepared according to the procedure of Lyleet al.(1953). To 50 ml of absolute ethanol saturated with hydrogen chloride, 10 g of p -methyl-acetophenone was added. After standing for 30 d, the reaction mixture was filtered and the solid residue was washed with cold absolute ethanol, giving pure 1,3,5-tris(4-methylphenyl)benzene. A small amount of product was obtained by pouring the above filtrate
Crystal data
C27H24
Mr= 348.46 Monoclinic,P21=c
a= 13.1640 (6) A˚
b= 15.2531 (9) A˚
c= 20.5554 (11) A˚
= 97.3083 (17)
V= 4093.8 (4) A˚3
Z= 8
Dx= 1.131 Mg m
3 MoKradiation Cell parameters from 9186
reflections
= 2.0–27.5 = 0.06 mm1
T= 293 (2) K Prism, yellow 0.430.210.15 mm
Data collection
Rigaku Weissenberg IP diffractometer Scintillation counter scans Absorption correction: multi-scan
(TEXSAN; Molecular Structure Corporation, 1998)
Tmin= 0.899,Tmax= 0.994 31594 measured reflections
9186 independent reflections 3366 reflections withI> 2(I)
Rint= 0.049 max= 27.5
h= 0!16
k= 0!19
l=26!26
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.054
wR(F2) = 0.102
S= 0.99 9186 reflections 487 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0251P)2] whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001
max= 0.19 e A˚
3
min=0.19 e A˚
[image:2.610.56.482.61.533.2]3
Table 1
Selected geometric parameters (A˚ ,).
C1—C7 1.486 (3) C3—C13 1.489 (3) C5—C19 1.477 (3) C10—C25 1.513 (3) C16—C26 1.520 (3) C22—C27 1.524 (3)
C28—C34 1.477 (3) C30—C40 1.490 (3) C32—C46 1.487 (3) C37—C52 1.520 (3) C43—C53 1.513 (3) C49—C54 1.516 (3)
C2—C1—C7 121.0 (2) C2—C3—C13 121.9 (2) C6—C5—C19 121.7 (2) C8—C7—C1 120.3 (2) C9—C10—C25 121.3 (2) C14—C13—C3 120.7 (2) C15—C16—C26 120.9 (2) C24—C19—C5 120.2 (2) C23—C22—C27 119.9 (3)
C29—C28—C34 119.9 (2) C29—C30—C40 120.4 (2) C33—C32—C46 121.1 (2) C35—C34—C28 120.9 (2) C36—C37—C52 121.6 (2) C41—C40—C30 120.8 (2) C42—C43—C53 120.8 (2) C51—C46—C32 121.0 (2) C50—C49—C54 121.2 (2)
All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with aromatic C—H = 0.93 A˚ and methyl C—H = 0.96 A˚ , andUiso(H) = 1.2Ueq(C) and 1.5Ueq(C) for aromatic and
methyl H atoms, respectively.
Data collection: TEXSAN (Molecular Structure Corporation, 1998); cell refinement: TEXSAN; data reduction: TEXSAN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics:SHELXL97; software used to prepare material for publication:SHELXL97.
[image:2.610.47.296.69.311.2]We are grateful for financial support from the Natural Science Foundation of Fujian Province, China (No. E0310016), and the Education Commission Foundation of Fujian Province, China (No. JB05309).
Figure 1
View of the asymmetric unit of (I), showing the atom-labelling scheme. All H atoms have been omitted for clarity.
Figure 2
[image:2.610.45.294.349.531.2]References
Elmorsy, S. S., Pelter, A. & Smith, K. (1991).Tetrahedron Lett.32, 4175–4176. Grilli, S., Lunazzi, L., Mazzanti, A. & Pinamonti, M. (2002).J. Org. Chem.67,
5733–5738.
Lindeman, S. V., Shklover, V. E., Struchkov, Yu. T., Khotina, I. A., Salykhova, T. M., Teplyakov, M. M. & Korshak, V. V. (1984).Makromol. Chem.185, 417–427.
Lyle, R. E., Dewitt, E. J., Nichols, N. M. & Cleland, W. (1953).J. Am. Chem. Soc.75, 5959–5961.
Molecular Structure Corporation (1998).TEXSAN. Version 1.9. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Go¨ttingen, Germany.
Thallapally, P. K., Chakraborty, K., Carrell, H. L., Kotha, S. & Desiraju, G. R. (2000).Tetrahedron,56, 6721–6728.
Tong, L., Ho, D. M., Vogelaar, N. J., Schutt, C. E. & Pascal, R. A. Jr (1997).J. Am. Chem. Soc.119, 7291–7302.
Weber, E., Hecker, M., Koepp, E., Orlia, W., Czugler, M. & Csoregh, I. (1988).
J. Chem. Soc. Perkin Trans. 2, pp. 1251–1257.
organic papers
Acta Cryst.(2006). E62, o777–o779 Liet al. C
supporting information
Acta Cryst. (2006). E62, o777–o779 [https://doi.org/10.1107/S160053680600256X]
1,3,5-Tris(4-methylphenyl)benzene
Zhong-Shui Li, Jian-Xin Chen, Yuan-Biao Huang, Gu-Rong Chen and Ting-Yan Lan
1,3,5-Tris(4-methylphenyl)benzene
Crystal data C27H24
Mr = 348.46 Monoclinic, P21/c
Hall symbol: -P 2ybc a = 13.1640 (6) Å b = 15.2531 (9) Å c = 20.5554 (11) Å β = 97.3083 (17)° V = 4093.8 (4) Å3
Z = 8
F(000) = 1488 Dx = 1.131 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 9186 reflections θ = 2.0–27.5°
µ = 0.06 mm−1
T = 293 K Prism, yellow
0.43 × 0.21 × 0.15 mm
Data collection Rigaku Weissenberg IP
diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
scintillation counter scans
Absorption correction: multi-scan
(TEXSAN; Molecular Structure Corporation, 1998)
Tmin = 0.899, Tmax = 0.994
31594 measured reflections 9186 independent reflections 3366 reflections with I > 2σ(I) Rint = 0.049
θmax = 27.5°, θmin = 2.0°
h = 0→16 k = 0→19 l = −26→26
Refinement Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.054
wR(F2) = 0.102
S = 0.99 9186 reflections 487 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0251P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.19 e Å−3
Δρmin = −0.19 e Å−3
Special details
supporting information
sup-2
Acta Cryst. (2006). E62, o777–o779
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. A part of the non-H atoms were determined from subsequence difference Fourier synthesis and all were refined with anisotropic thermal parameters with full-matrix least-squares techniques on F2.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
C1 0.37360 (15) 0.45760 (13) 0.19232 (10) 0.0517 (5)
C2 0.43648 (15) 0.43696 (13) 0.14457 (10) 0.0559 (6)
H2A 0.4615 0.4820 0.1205 0.067*
C3 0.46272 (15) 0.35033 (14) 0.13212 (10) 0.0538 (5)
C4 0.42590 (15) 0.28403 (14) 0.16902 (10) 0.0558 (6)
H4A 0.4421 0.2261 0.1608 0.067*
C5 0.36509 (15) 0.30230 (13) 0.21820 (10) 0.0534 (6)
C6 0.34042 (15) 0.38992 (14) 0.22937 (10) 0.0556 (6)
H6A 0.3008 0.4030 0.2625 0.067*
C7 0.34585 (15) 0.54999 (13) 0.20481 (9) 0.0508 (5)
C8 0.24968 (15) 0.57004 (15) 0.22301 (10) 0.0627 (6)
H8A 0.2028 0.5254 0.2272 0.075*
C9 0.22399 (17) 0.65652 (16) 0.23483 (10) 0.0670 (6)
H9A 0.1601 0.6685 0.2475 0.080*
C10 0.28998 (18) 0.72485 (14) 0.22843 (10) 0.0607 (6)
C11 0.38481 (17) 0.70472 (14) 0.21118 (10) 0.0611 (6)
H11A 0.4313 0.7497 0.2071 0.073*
C12 0.41277 (16) 0.61878 (13) 0.19976 (10) 0.0569 (6)
H12A 0.4777 0.6073 0.1885 0.068*
C13 0.53453 (15) 0.32807 (13) 0.08416 (10) 0.0528 (5)
C14 0.60938 (17) 0.26480 (14) 0.09862 (11) 0.0641 (6)
H14A 0.6122 0.2342 0.1379 0.077*
C15 0.68023 (16) 0.24578 (15) 0.05628 (11) 0.0676 (6)
H15A 0.7302 0.2035 0.0680 0.081*
C16 0.67780 (18) 0.28812 (16) −0.00229 (11) 0.0664 (6)
C17 0.6028 (2) 0.34971 (16) −0.01783 (11) 0.0822 (7)
H17A 0.5993 0.3787 −0.0578 0.099*
C18 0.53174 (18) 0.37008 (15) 0.02432 (11) 0.0730 (7)
H18A 0.4819 0.4123 0.0122 0.088*
C19 0.33637 (14) 0.23076 (14) 0.26074 (12) 0.0556 (6)
C20 0.30599 (15) 0.14892 (15) 0.23588 (12) 0.0671 (7)
H20A 0.2986 0.1396 0.1908 0.081*
C21 0.28671 (17) 0.08156 (16) 0.27690 (17) 0.0832 (8)
H21A 0.2662 0.0274 0.2590 0.100*
C22 0.29705 (18) 0.09224 (18) 0.34372 (17) 0.0809 (8)
C23 0.32502 (18) 0.17392 (18) 0.36884 (13) 0.0811 (8)
H23A 0.3310 0.1830 0.4139 0.097*
H24A 0.3627 0.2971 0.3461 0.081*
C25 0.25928 (18) 0.81877 (14) 0.23946 (12) 0.0861 (8)
H25A 0.3148 0.8572 0.2328 0.129*
H25B 0.2434 0.8253 0.2835 0.129*
H25C 0.2002 0.8335 0.2091 0.129*
C26 0.75435 (19) 0.26601 (18) −0.04930 (12) 0.1003 (9)
H26A 0.8003 0.2214 −0.0303 0.150*
H26B 0.7927 0.3176 −0.0573 0.150*
H26C 0.7184 0.2451 −0.0899 0.150*
C27 0.2804 (2) 0.01707 (18) 0.39008 (16) 0.1304 (12)
H27A 0.2614 −0.0348 0.3650 0.196*
H27B 0.2268 0.0323 0.4156 0.196*
H27C 0.3425 0.0064 0.4188 0.196*
C28 0.12408 (16) 0.20754 (14) 0.06644 (10) 0.0567 (6)
C29 0.20013 (17) 0.18572 (14) 0.02801 (10) 0.0609 (6)
H29A 0.2341 0.2301 0.0084 0.073*
C30 0.22625 (16) 0.09853 (14) 0.01834 (10) 0.0576 (6)
C31 0.17545 (16) 0.03278 (14) 0.04838 (10) 0.0610 (6)
H31A 0.1919 −0.0256 0.0417 0.073*
C32 0.10026 (16) 0.05280 (14) 0.08834 (10) 0.0580 (6)
C33 0.07574 (16) 0.14052 (14) 0.09626 (10) 0.0600 (6)
H33A 0.0254 0.1547 0.1224 0.072*
C34 0.09483 (17) 0.30024 (14) 0.07340 (10) 0.0578 (6)
C35 −0.00618 (17) 0.32339 (15) 0.07830 (11) 0.0752 (7)
H35A −0.0559 0.2799 0.0771 0.090*
C36 −0.03353 (19) 0.40995 (16) 0.08492 (12) 0.0847 (8)
H36A −0.1017 0.4233 0.0879 0.102*
C37 0.0368 (2) 0.47737 (15) 0.08725 (11) 0.0702 (7)
C38 0.13630 (18) 0.45454 (15) 0.08176 (10) 0.0698 (7)
H38A 0.1856 0.4983 0.0825 0.084*
C39 0.16502 (17) 0.36792 (15) 0.07515 (10) 0.0672 (6)
H39A 0.2332 0.3550 0.0718 0.081*
C40 0.30755 (17) 0.07646 (14) −0.02318 (10) 0.0570 (6)
C41 0.40143 (18) 0.11994 (15) −0.01477 (10) 0.0663 (6)
H41A 0.4132 0.1634 0.0170 0.080*
C42 0.47762 (18) 0.09931 (16) −0.05319 (11) 0.0703 (7)
H42A 0.5395 0.1295 −0.0469 0.084*
C43 0.46306 (18) 0.03493 (16) −0.10043 (11) 0.0656 (6)
C44 0.37007 (19) −0.00755 (15) −0.10880 (11) 0.0704 (7)
H44A 0.3584 −0.0508 −0.1408 0.085*
C45 0.29308 (18) 0.01243 (15) −0.07081 (11) 0.0678 (6)
H45A 0.2312 −0.0177 −0.0776 0.081*
C46 0.05166 (15) −0.01760 (14) 0.12379 (11) 0.0576 (6)
C47 0.02522 (17) −0.09781 (16) 0.09480 (12) 0.0707 (7)
H47A 0.0354 −0.1071 0.0514 0.085*
C48 −0.01594 (17) −0.16412 (16) 0.12886 (13) 0.0751 (7)
H48A −0.0337 −0.2169 0.1078 0.090*
supporting information
sup-4
Acta Cryst. (2006). E62, o777–o779
C50 −0.00743 (17) −0.07306 (17) 0.22193 (12) 0.0737 (7)
H50A −0.0190 −0.0636 0.2651 0.088*
C51 0.03313 (16) −0.00605 (15) 0.18819 (11) 0.0684 (6)
H51A 0.0482 0.0475 0.2089 0.082*
C52 0.00553 (19) 0.57231 (14) 0.09514 (13) 0.0922 (8)
H52A 0.0645 0.6094 0.0957 0.138*
H52B −0.0231 0.5789 0.1356 0.138*
H52C −0.0446 0.5886 0.0591 0.138*
C53 0.54673 (18) 0.01234 (17) −0.14167 (11) 0.0925 (8)
H53A 0.5232 −0.0332 −0.1722 0.139*
H53B 0.6062 −0.0075 −0.1137 0.139*
H53C 0.5638 0.0634 −0.1653 0.139*
C54 −0.07041 (18) −0.22810 (16) 0.23240 (12) 0.0975 (9)
H54A −0.0830 −0.2787 0.2047 0.146*
H54B −0.1329 −0.2106 0.2482 0.146*
H54C −0.0201 −0.2422 0.2689 0.146*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.0531 (13) 0.0465 (14) 0.0541 (14) 0.0025 (11) 0.0016 (11) −0.0028 (11)
C2 0.0612 (13) 0.0459 (14) 0.0600 (15) 0.0036 (11) 0.0051 (11) 0.0002 (11)
C3 0.0592 (14) 0.0485 (14) 0.0525 (14) 0.0052 (11) 0.0025 (11) 0.0009 (11)
C4 0.0610 (14) 0.0440 (13) 0.0623 (15) 0.0049 (11) 0.0074 (12) −0.0023 (12)
C5 0.0528 (13) 0.0450 (14) 0.0614 (15) −0.0030 (11) 0.0030 (11) −0.0027 (12)
C6 0.0560 (13) 0.0508 (14) 0.0597 (15) 0.0019 (11) 0.0056 (11) −0.0062 (12)
C7 0.0560 (13) 0.0453 (13) 0.0497 (14) 0.0024 (11) 0.0013 (10) −0.0051 (10)
C8 0.0548 (14) 0.0595 (15) 0.0735 (16) −0.0028 (12) 0.0076 (12) −0.0087 (12)
C9 0.0603 (15) 0.0672 (17) 0.0737 (17) 0.0160 (13) 0.0095 (12) −0.0109 (13)
C10 0.0687 (15) 0.0473 (14) 0.0626 (15) 0.0107 (13) −0.0048 (12) −0.0119 (12)
C11 0.0592 (14) 0.0489 (14) 0.0729 (16) −0.0036 (12) −0.0005 (12) −0.0054 (12)
C12 0.0559 (13) 0.0512 (14) 0.0618 (15) 0.0063 (12) 0.0004 (11) −0.0065 (12)
C13 0.0640 (14) 0.0448 (13) 0.0494 (14) 0.0018 (11) 0.0067 (11) −0.0032 (11)
C14 0.0758 (15) 0.0574 (15) 0.0600 (15) 0.0086 (13) 0.0122 (13) 0.0071 (12)
C15 0.0695 (15) 0.0682 (17) 0.0667 (16) 0.0130 (13) 0.0146 (13) 0.0002 (14)
C16 0.0775 (16) 0.0697 (17) 0.0533 (16) −0.0012 (14) 0.0139 (13) −0.0035 (13)
C17 0.111 (2) 0.0851 (19) 0.0515 (16) 0.0150 (17) 0.0148 (15) 0.0109 (14)
C18 0.0898 (17) 0.0690 (17) 0.0597 (16) 0.0214 (14) 0.0081 (13) 0.0083 (14)
C19 0.0457 (12) 0.0482 (14) 0.0738 (17) 0.0020 (11) 0.0118 (11) 0.0003 (13)
C20 0.0594 (15) 0.0499 (15) 0.0932 (19) −0.0027 (12) 0.0138 (13) −0.0050 (14)
C21 0.0612 (15) 0.0474 (16) 0.144 (3) −0.0046 (12) 0.0256 (17) 0.0006 (19)
C22 0.0592 (15) 0.0591 (18) 0.131 (3) 0.0084 (13) 0.0385 (17) 0.0283 (18)
C23 0.0791 (17) 0.0771 (19) 0.092 (2) 0.0062 (16) 0.0293 (14) 0.0205 (17)
C24 0.0733 (15) 0.0527 (15) 0.0773 (18) −0.0039 (12) 0.0172 (13) 0.0047 (14)
C25 0.0917 (18) 0.0550 (16) 0.109 (2) 0.0181 (14) 0.0013 (15) −0.0175 (14)
C26 0.100 (2) 0.131 (3) 0.0769 (18) 0.0118 (18) 0.0369 (16) −0.0057 (17)
C27 0.108 (2) 0.087 (2) 0.208 (3) 0.0070 (18) 0.070 (2) 0.065 (2)
C29 0.0732 (15) 0.0538 (15) 0.0551 (15) −0.0019 (12) 0.0057 (12) 0.0022 (12)
C30 0.0695 (14) 0.0504 (14) 0.0532 (15) 0.0052 (12) 0.0087 (12) −0.0012 (12)
C31 0.0747 (16) 0.0499 (14) 0.0580 (15) 0.0043 (12) 0.0070 (12) −0.0011 (12)
C32 0.0649 (14) 0.0514 (15) 0.0563 (15) 0.0042 (12) 0.0027 (12) 0.0010 (12)
C33 0.0673 (14) 0.0558 (15) 0.0577 (15) 0.0053 (12) 0.0107 (11) −0.0013 (12)
C34 0.0605 (14) 0.0517 (14) 0.0598 (15) 0.0054 (12) 0.0020 (11) −0.0031 (12)
C35 0.0679 (16) 0.0551 (16) 0.102 (2) 0.0000 (13) 0.0100 (14) −0.0031 (14)
C36 0.0697 (16) 0.0639 (18) 0.120 (2) 0.0123 (15) 0.0104 (15) −0.0055 (16)
C37 0.0826 (18) 0.0500 (15) 0.0748 (17) 0.0133 (14) −0.0020 (14) −0.0077 (12)
C38 0.0715 (17) 0.0523 (15) 0.0820 (19) 0.0014 (13) −0.0040 (13) −0.0068 (13)
C39 0.0640 (15) 0.0590 (16) 0.0761 (17) 0.0074 (13) −0.0007 (12) −0.0071 (13)
C40 0.0675 (15) 0.0510 (14) 0.0528 (14) 0.0058 (12) 0.0086 (12) −0.0003 (12)
C41 0.0774 (16) 0.0603 (15) 0.0617 (15) 0.0015 (13) 0.0100 (13) −0.0044 (12)
C42 0.0685 (15) 0.0748 (17) 0.0682 (17) −0.0015 (13) 0.0107 (13) 0.0053 (14)
C43 0.0707 (16) 0.0691 (16) 0.0576 (15) 0.0117 (14) 0.0109 (13) 0.0105 (13)
C44 0.0893 (19) 0.0581 (15) 0.0649 (16) 0.0095 (14) 0.0138 (14) −0.0048 (12)
C45 0.0726 (15) 0.0610 (16) 0.0709 (17) −0.0046 (13) 0.0131 (13) −0.0080 (13)
C46 0.0599 (14) 0.0546 (15) 0.0579 (15) 0.0021 (12) 0.0065 (11) 0.0024 (12)
C47 0.0807 (16) 0.0656 (17) 0.0652 (17) −0.0048 (14) 0.0061 (13) −0.0022 (14)
C48 0.0802 (17) 0.0587 (16) 0.085 (2) −0.0083 (14) 0.0045 (15) 0.0028 (15)
C49 0.0534 (14) 0.0665 (18) 0.091 (2) −0.0028 (13) 0.0135 (13) 0.0115 (16)
C50 0.0719 (15) 0.0826 (19) 0.0703 (17) 0.0064 (15) 0.0240 (13) 0.0081 (16)
C51 0.0772 (16) 0.0623 (16) 0.0672 (17) 0.0030 (13) 0.0153 (13) −0.0013 (14)
C52 0.104 (2) 0.0561 (16) 0.113 (2) 0.0160 (15) 0.0024 (16) −0.0113 (15)
C53 0.0918 (18) 0.116 (2) 0.0744 (18) 0.0238 (17) 0.0283 (15) 0.0033 (16)
C54 0.0802 (17) 0.094 (2) 0.123 (2) −0.0112 (16) 0.0282 (16) 0.0301 (18)
Geometric parameters (Å, º)
C1—C6 1.386 (3) C28—C33 1.387 (3)
C1—C2 1.398 (3) C28—C29 1.392 (3)
C1—C7 1.486 (3) C28—C34 1.477 (3)
C2—C3 1.398 (3) C29—C30 1.394 (3)
C2—H2A 0.9300 C29—H29A 0.9300
C3—C4 1.388 (3) C30—C31 1.393 (3)
C3—C13 1.489 (3) C30—C40 1.490 (3)
C4—C5 1.395 (2) C31—C32 1.398 (3)
C4—H4A 0.9300 C31—H31A 0.9300
C5—C6 1.401 (3) C32—C33 1.391 (3)
C5—C19 1.477 (3) C32—C46 1.487 (3)
C6—H6A 0.9300 C33—H33A 0.9300
C7—C12 1.382 (3) C34—C39 1.383 (3)
C7—C8 1.399 (3) C34—C35 1.392 (3)
C8—C9 1.391 (3) C35—C36 1.380 (3)
C8—H8A 0.9300 C35—H35A 0.9300
C9—C10 1.374 (3) C36—C37 1.381 (3)
C9—H9A 0.9300 C36—H36A 0.9300
supporting information
sup-6
Acta Cryst. (2006). E62, o777–o779
C10—C25 1.513 (3) C37—C52 1.520 (3)
C11—C12 1.390 (3) C38—C39 1.386 (3)
C11—H11A 0.9300 C38—H38A 0.9300
C12—H12A 0.9300 C39—H39A 0.9300
C13—C18 1.383 (3) C40—C45 1.379 (3)
C13—C14 1.384 (3) C40—C41 1.394 (3)
C14—C15 1.385 (3) C41—C42 1.389 (3)
C14—H14A 0.9300 C41—H41A 0.9300
C15—C16 1.363 (3) C42—C43 1.377 (3)
C15—H15A 0.9300 C42—H42A 0.9300
C16—C17 1.371 (3) C43—C44 1.376 (3)
C16—C26 1.520 (3) C43—C53 1.513 (3)
C17—C18 1.388 (3) C44—C45 1.390 (3)
C17—H17A 0.9300 C44—H44A 0.9300
C18—H18A 0.9300 C45—H45A 0.9300
C19—C24 1.387 (3) C46—C47 1.386 (3)
C19—C20 1.388 (3) C46—C51 1.388 (3)
C20—C21 1.373 (3) C47—C48 1.380 (3)
C20—H20A 0.9300 C47—H47A 0.9300
C21—C22 1.373 (3) C48—C49 1.379 (3)
C21—H21A 0.9300 C48—H48A 0.9300
C22—C23 1.381 (3) C49—C50 1.381 (3)
C22—C27 1.524 (3) C49—C54 1.516 (3)
C23—C24 1.384 (3) C50—C51 1.380 (3)
C23—H23A 0.9300 C50—H50A 0.9300
C24—H24A 0.9300 C51—H51A 0.9300
C25—H25A 0.9600 C52—H52A 0.9600
C25—H25B 0.9600 C52—H52B 0.9600
C25—H25C 0.9600 C52—H52C 0.9600
C26—H26A 0.9600 C53—H53A 0.9600
C26—H26B 0.9600 C53—H53B 0.9600
C26—H26C 0.9600 C53—H53C 0.9600
C27—H27A 0.9600 C54—H54A 0.9600
C27—H27B 0.9600 C54—H54B 0.9600
C27—H27C 0.9600 C54—H54C 0.9600
C6—C1—C2 118.3 (2) C33—C28—C29 118.5 (2)
C6—C1—C7 120.65 (19) C33—C28—C34 121.5 (2)
C2—C1—C7 121.0 (2) C29—C28—C34 119.9 (2)
C3—C2—C1 121.6 (2) C28—C29—C30 121.1 (2)
C3—C2—H2A 119.2 C28—C29—H29A 119.4
C1—C2—H2A 119.2 C30—C29—H29A 119.4
C4—C3—C2 118.5 (2) C31—C30—C29 118.9 (2)
C4—C3—C13 119.40 (19) C31—C30—C40 120.8 (2)
C2—C3—C13 121.9 (2) C29—C30—C40 120.4 (2)
C3—C4—C5 121.5 (2) C30—C31—C32 121.3 (2)
C3—C4—H4A 119.2 C30—C31—H31A 119.4
C4—C5—C6 118.4 (2) C33—C32—C31 118.1 (2)
C4—C5—C19 119.68 (19) C33—C32—C46 121.1 (2)
C6—C5—C19 121.7 (2) C31—C32—C46 120.7 (2)
C1—C6—C5 121.6 (2) C28—C33—C32 122.1 (2)
C1—C6—H6A 119.2 C28—C33—H33A 119.0
C5—C6—H6A 119.2 C32—C33—H33A 119.0
C12—C7—C8 117.46 (19) C39—C34—C35 116.7 (2)
C12—C7—C1 122.26 (19) C39—C34—C28 122.4 (2)
C8—C7—C1 120.3 (2) C35—C34—C28 120.9 (2)
C9—C8—C7 120.2 (2) C36—C35—C34 120.9 (2)
C9—C8—H8A 119.9 C36—C35—H35A 119.5
C7—C8—H8A 119.9 C34—C35—H35A 119.5
C10—C9—C8 122.1 (2) C35—C36—C37 122.3 (2)
C10—C9—H9A 118.9 C35—C36—H36A 118.9
C8—C9—H9A 118.9 C37—C36—H36A 118.9
C9—C10—C11 117.5 (2) C38—C37—C36 116.8 (2)
C9—C10—C25 121.3 (2) C38—C37—C52 121.6 (2)
C11—C10—C25 121.2 (2) C36—C37—C52 121.6 (2)
C10—C11—C12 121.5 (2) C37—C38—C39 121.6 (2)
C10—C11—H11A 119.2 C37—C38—H38A 119.2
C12—C11—H11A 119.2 C39—C38—H38A 119.2
C7—C12—C11 121.23 (19) C34—C39—C38 121.6 (2)
C7—C12—H12A 119.4 C34—C39—H39A 119.2
C11—C12—H12A 119.4 C38—C39—H39A 119.2
C18—C13—C14 116.8 (2) C45—C40—C41 117.7 (2)
C18—C13—C3 122.4 (2) C45—C40—C30 121.5 (2)
C14—C13—C3 120.7 (2) C41—C40—C30 120.8 (2)
C13—C14—C15 121.9 (2) C42—C41—C40 121.0 (2)
C13—C14—H14A 119.0 C42—C41—H41A 119.5
C15—C14—H14A 119.0 C40—C41—H41A 119.5
C16—C15—C14 120.9 (2) C43—C42—C41 121.1 (2)
C16—C15—H15A 119.5 C43—C42—H42A 119.5
C14—C15—H15A 119.5 C41—C42—H42A 119.4
C15—C16—C17 117.8 (2) C44—C43—C42 117.8 (2)
C15—C16—C26 120.9 (2) C44—C43—C53 121.5 (2)
C17—C16—C26 121.3 (2) C42—C43—C53 120.8 (2)
C16—C17—C18 122.0 (2) C43—C44—C45 121.8 (2)
C16—C17—H17A 119.0 C43—C44—H44A 119.1
C18—C17—H17A 119.0 C45—C44—H44A 119.1
C13—C18—C17 120.5 (2) C40—C45—C44 120.6 (2)
C13—C18—H18A 119.8 C40—C45—H45A 119.7
C17—C18—H18A 119.8 C44—C45—H45A 119.7
C24—C19—C20 117.7 (2) C47—C46—C51 117.2 (2)
C24—C19—C5 120.2 (2) C47—C46—C32 121.8 (2)
C20—C19—C5 122.0 (2) C51—C46—C32 121.0 (2)
C21—C20—C19 120.9 (2) C48—C47—C46 121.5 (2)
C21—C20—H20A 119.5 C48—C47—H47A 119.3
supporting information
sup-8
Acta Cryst. (2006). E62, o777–o779
C22—C21—C20 121.5 (3) C49—C48—C47 121.3 (2)
C22—C21—H21A 119.2 C49—C48—H48A 119.3
C20—C21—H21A 119.2 C47—C48—H48A 119.3
C21—C22—C23 118.0 (2) C48—C49—C50 117.2 (2)
C21—C22—C27 122.2 (3) C48—C49—C54 121.6 (2)
C23—C22—C27 119.9 (3) C50—C49—C54 121.2 (2)
C22—C23—C24 121.1 (3) C51—C50—C49 121.9 (2)
C22—C23—H23A 119.4 C51—C50—H50A 119.0
C24—C23—H23A 119.4 C49—C50—H50A 119.0
C23—C24—C19 120.7 (2) C50—C51—C46 120.8 (2)
C23—C24—H24A 119.7 C50—C51—H51A 119.6
C19—C24—H24A 119.7 C46—C51—H51A 119.6
C10—C25—H25A 109.5 C37—C52—H52A 109.5
C10—C25—H25B 109.5 C37—C52—H52B 109.5
H25A—C25—H25B 109.5 H52A—C52—H52B 109.5
C10—C25—H25C 109.5 C37—C52—H52C 109.5
H25A—C25—H25C 109.5 H52A—C52—H52C 109.5
H25B—C25—H25C 109.5 H52B—C52—H52C 109.5
C16—C26—H26A 109.5 C43—C53—H53A 109.5
C16—C26—H26B 109.5 C43—C53—H53B 109.5
H26A—C26—H26B 109.5 H53A—C53—H53B 109.5
C16—C26—H26C 109.5 C43—C53—H53C 109.5
H26A—C26—H26C 109.5 H53A—C53—H53C 109.5
H26B—C26—H26C 109.5 H53B—C53—H53C 109.5
C22—C27—H27A 109.5 C49—C54—H54A 109.5
C22—C27—H27B 109.5 C49—C54—H54B 109.5
H27A—C27—H27B 109.5 H54A—C54—H54B 109.5
C22—C27—H27C 109.5 C49—C54—H54C 109.5
H27A—C27—H27C 109.5 H54A—C54—H54C 109.5
H27B—C27—H27C 109.5 H54B—C54—H54C 109.5
C6—C1—C2—C3 2.5 (3) C33—C28—C29—C30 1.3 (3)
C7—C1—C2—C3 −179.67 (18) C34—C28—C29—C30 −177.28 (19)
C1—C2—C3—C4 −0.8 (3) C28—C29—C30—C31 −0.6 (3)
C1—C2—C3—C13 −176.33 (18) C28—C29—C30—C40 179.74 (19)
C2—C3—C4—C5 −0.8 (3) C29—C30—C31—C32 −0.8 (3)
C13—C3—C4—C5 174.81 (18) C40—C30—C31—C32 178.9 (2)
C3—C4—C5—C6 0.8 (3) C30—C31—C32—C33 1.4 (3)
C3—C4—C5—C19 −173.77 (19) C30—C31—C32—C46 −175.78 (19)
C2—C1—C6—C5 −2.5 (3) C29—C28—C33—C32 −0.7 (3)
C7—C1—C6—C5 179.59 (17) C34—C28—C33—C32 177.86 (19)
C4—C5—C6—C1 1.0 (3) C31—C32—C33—C28 −0.6 (3)
C19—C5—C6—C1 175.38 (18) C46—C32—C33—C28 176.50 (19)
C6—C1—C7—C12 143.2 (2) C33—C28—C34—C39 146.6 (2)
C2—C1—C7—C12 −34.6 (3) C29—C28—C34—C39 −34.9 (3)
C6—C1—C7—C8 −36.1 (3) C33—C28—C34—C35 −33.6 (3)
C2—C1—C7—C8 146.07 (19) C29—C28—C34—C35 144.9 (2)
C1—C7—C8—C9 179.84 (19) C28—C34—C35—C36 179.9 (2)
C7—C8—C9—C10 0.9 (3) C34—C35—C36—C37 −0.2 (4)
C8—C9—C10—C11 −1.5 (3) C35—C36—C37—C38 0.8 (4)
C8—C9—C10—C25 178.1 (2) C35—C36—C37—C52 −179.5 (2)
C9—C10—C11—C12 0.8 (3) C36—C37—C38—C39 −0.9 (3)
C25—C10—C11—C12 −178.8 (2) C52—C37—C38—C39 179.4 (2)
C8—C7—C12—C11 −1.1 (3) C35—C34—C39—C38 0.3 (3)
C1—C7—C12—C11 179.49 (19) C28—C34—C39—C38 −179.9 (2)
C10—C11—C12—C7 0.5 (3) C37—C38—C39—C34 0.3 (3)
C4—C3—C13—C18 143.2 (2) C31—C30—C40—C45 47.7 (3)
C2—C3—C13—C18 −41.4 (3) C29—C30—C40—C45 −132.6 (2)
C4—C3—C13—C14 −38.3 (3) C31—C30—C40—C41 −132.0 (2)
C2—C3—C13—C14 137.2 (2) C29—C30—C40—C41 47.7 (3)
C18—C13—C14—C15 1.8 (3) C45—C40—C41—C42 0.0 (3)
C3—C13—C14—C15 −176.86 (19) C30—C40—C41—C42 179.7 (2)
C13—C14—C15—C16 −1.1 (3) C40—C41—C42—C43 −0.4 (3)
C14—C15—C16—C17 −0.3 (3) C41—C42—C43—C44 0.7 (3)
C14—C15—C16—C26 −178.9 (2) C41—C42—C43—C53 −179.5 (2)
C15—C16—C17—C18 0.8 (4) C42—C43—C44—C45 −0.7 (3)
C26—C16—C17—C18 179.4 (2) C53—C43—C44—C45 179.6 (2)
C14—C13—C18—C17 −1.2 (3) C41—C40—C45—C44 0.0 (3)
C3—C13—C18—C17 177.4 (2) C30—C40—C45—C44 −179.6 (2)
C16—C17—C18—C13 −0.1 (4) C43—C44—C45—C40 0.3 (3)
C4—C5—C19—C24 134.2 (2) C33—C32—C46—C47 142.6 (2)
C6—C5—C19—C24 −40.2 (3) C31—C32—C46—C47 −40.3 (3)
C4—C5—C19—C20 −42.5 (3) C33—C32—C46—C51 −38.9 (3)
C6—C5—C19—C20 143.2 (2) C31—C32—C46—C51 138.1 (2)
C24—C19—C20—C21 −1.4 (3) C51—C46—C47—C48 −1.3 (3)
C5—C19—C20—C21 175.3 (2) C32—C46—C47—C48 177.3 (2)
C19—C20—C21—C22 −0.3 (3) C46—C47—C48—C49 −0.8 (4)
C20—C21—C22—C23 1.7 (4) C47—C48—C49—C50 2.4 (3)
C20—C21—C22—C27 −177.3 (2) C47—C48—C49—C54 −176.2 (2)
C21—C22—C23—C24 −1.4 (4) C48—C49—C50—C51 −2.0 (3)
C27—C22—C23—C24 177.6 (2) C54—C49—C50—C51 176.7 (2)
C22—C23—C24—C19 −0.3 (3) C49—C50—C51—C46 −0.1 (3)
C20—C19—C24—C23 1.7 (3) C47—C46—C51—C50 1.7 (3)
