Acta Cryst.(2002). E58, o129±o131 DOI: 10.1107/S1600536802000302 Jeffrey C. Bryanet al. C40H44O8
o129
organic papers
Acta Crystallographica Section E
Structure Reports
Online ISSN 1600-5368
(9,10-Triptyceno)benzo-28-crown-8
Jeffrey C. Bryan,a* Andrei A.
Gakhband Richard A.
Sachlebenc
aChemical Sciences Division, Oak Ridge
National Laboratory, Oak Ridge, TN 37831-6119, USA,bChemical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, TN 37831-6197, USA, andcUS House of Representatives, Committee on Science, Energy Subcommittee, 390 Ford House Office Building, Washington, DC 20515, USA
Correspondence e-mail: [email protected]
Key indicators Single-crystal X-ray study
T= 233 K
Mean(C±C) = 0.004 AÊ Disorder in main residue
Rfactor = 0.048
wRfactor = 0.134
Data-to-parameter ratio = 12.4
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved
The structure of the title compound, C40H44O8, differs from
previously determined structures of triptyceno±crown ether molecules as its longer crown ether chain does not congest a triptycene cavity.
Comment
We have studied triptycene-substituted crown ether rings as molecular gearing systems (Gakh et al., 1997; Bryan et al., 1999) and as potential recognition agents for cations with a low charge-to-size ratio (Gakh et al., 1995). Since the steric demands of inserting the relatively large triptycene group into 18-crown-6 or 21-crown-7 resulted in an elliptically shaped cavity, poorly suited for binding spherical cations (Gakhet al., 1995; Bryan et al., 1999), we decided to investigate the title compound, (I).
The title compound can be thought of as the result of inserting a triptycene group into benzo-24-crown-8. The crown ring does not collapse in on itself to the extent normally observed for large crown ether molecules (Bryanet al., 2000, and references therein). In contrast to the previously deter-mined structures of triptyceno-22-crown-6 (Bryan,et al., 1999) and triptyceno-25-crown-7 (Gakhet al., 1995), the crown ether does not ®ll the space between two triptycene arene rings, but is elongated away from it. As a result, the inter-arene angles of the triptycene group are all close to 120, whereas the smaller
crown segments force a larger inter-arene angle between the two rings occupied by the crown. The inter-arene angles for the triptycene group in the title compound are: A1ÐA2 = 121.7 (1),A1ÐA3 = 119.4 (1), andA2ÐA3 = 118.9 (1), where
A1 = C3±8,A2 = C9±14, andA3 = C15±20.
Experimental
The compound was prepared as previously described (Gakhet al., 1997). Crystals were grown from 2-methoxyethanol. Similarly sized crystals were also found to grow from 2-propanol.
Crystal data
C40H44O8
Mr= 652.8 Monoclinic,P21=c
a= 9.3198 (17) AÊ
b= 23.416 (2) AÊ
c= 15.838 (3) AÊ
= 91.333 (9) V= 3455.4 (10) AÊ3
Z= 4
Dx= 1.255 Mg mÿ3
Mo Kradiation Cell parameters from 25
re¯ections
= 10.1±12.2
= 0.09 mmÿ1
T= 233 K Plate, colorless 0.630.500.04 mm
Data collection
Enraf±Nonius CAD-4 diffractometer
!scans
Absorption correction: none 7830 measured re¯ections 6061 independent re¯ections 3227 re¯ections withI> 2(I)
Rint= 0.029
max= 25.0
h= 0!11
k=ÿ16!27
l=ÿ18!18 3 standard re¯ections
frequency: 120 min intensity decay: 2%
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.048
wR(F2) = 0.134
S= 1.01 6061 re¯ections 487 parameters
H-atom parameters constrained
w= 1/[2(Fo2) + (0.061P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 0.27 e AÊÿ3
=ÿ0.28 e AÊÿ3
Table 1
Selected geometric parameters (AÊ,).
O1ÐC21 1.411 (3) O1ÐC22 1.411 (3) O2ÐC23 1.418 (3) O2ÐC24 1.412 (3) O3ÐC25 1.412 (3) O3ÐC26 1.415 (3) O4ÐC27 1.426 (3) O4ÐC28 1.384 (3) O5ÐC29 1.362 (3) O5ÐC34 1.475 (12) O5ÐC34A 1.35 (3)
O6ÐC35 1.414 (9) O6ÐC36 1.394 (7) O6AÐC35A 1.407 (15) O6AÐC36A 1.425 (14) O7ÐC37 1.443 (16) O7ÐC38 1.469 (16) O7AÐC38 1.33 (3) O7AÐC37A 1.43 (3) O8ÐC39 1.420 (3) O8ÐC40 1.422 (3) C21ÐO1ÐC22 113.47 (18)
C23ÐO2ÐC24 111.13 (19) C25ÐO3ÐC26 112.36 (19) C27ÐO4ÐC28 113.36 (19) C29ÐO5ÐC34 113.7 (5) C29ÐO5ÐC34A 128.4 (12) C35ÐO6ÐC36 113.6 (5) C35AÐO6AÐC36A 111.7 (10) C37ÐO7ÐC38 113.4 (9) C37AÐO7AÐC38 115.8 (18) C39ÐO8ÐC40 111.68 (19) O1ÐC21ÐC1 109.53 (19) O1ÐC22ÐC23 108.41 (19) O2ÐC23ÐC22 109.29 (18) O2ÐC24ÐC25 110.3 (2) O3ÐC25ÐC24 109.8 (2) O3ÐC26ÐC27 109.5 (2)
O4ÐC27ÐC26 109.7 (2) O4ÐC28ÐC29 120.8 (2) O4ÐC28ÐC33 118.9 (2) O5ÐC29ÐC30 124.9 (2) O5ÐC29ÐC28 116.3 (2) O5ÐC34ÐC35 105.6 (9) O5ÐC34AÐC35A 114 (2) O6ÐC35ÐC34 107.2 (8) O6AÐC35AÐC34A 109.0 (15) O6ÐC36ÐC37 116.3 (5) O6AÐC36AÐC37A 109.9 (10) O7ÐC37ÐC36 107.9 (8) O7AÐC37AÐC36A 106.5 (16) O7ÐC38ÐC39 117.8 (7) O7AÐC38ÐC39 108.5 (13) O8ÐC39ÐC38 108.9 (2) O8ÐC40ÐC2 110.16 (19) C22ÐO1ÐC21ÐC1 175.73 (17)
C21ÐO1ÐC22ÐC23 175.31 (18) C24ÐO2ÐC23ÐC22 173.31 (19) C23ÐO2ÐC24ÐC25 174.2 (2) C26ÐO3ÐC25ÐC24 ÿ174.6 (2) C25ÐO3ÐC26ÐC27 ÿ168.7 (2) C28ÐO4ÐC27ÐC26 153.3 (2) C27ÐO4ÐC28ÐC29 89.3 (3) C27ÐO4ÐC28ÐC33 ÿ91.9 (3) C34ÐO5ÐC29ÐC28 174.9 (6) C34ÐO5ÐC29ÐC30 ÿ4.8 (7) C29ÐO5ÐC34ÐC35 ÿ168.9 (7) C36ÐO6ÐC35ÐC34 ÿ151.2 (8)
C35ÐO6ÐC36ÐC37 ÿ93.9 (7) C38ÐO7ÐC37ÐC36 ÿ165.9 (8) C37ÐO7ÐC38ÐC39 ÿ81.4 (11) C40ÐO8ÐC39ÐC38 168.9 (2) C39ÐO8ÐC40ÐC2 167.38 (19) O1ÐC22ÐC23ÐO2 ÿ76.4 (2) O2ÐC24ÐC25ÐO3 74.4 (3) O3ÐC26ÐC27ÐO4 75.3 (3) O4ÐC28ÐC29ÐO5 ÿ2.1 (4) O5ÐC34ÐC35ÐO6 178.7 (8) O6ÐC36ÐC37ÐO7 ÿ73.0 (9) O7ÐC38ÐC39ÐO8 68.5 (7)
Part of the crown ring (between C34 and O7) is disordered, and was modeled over two sites (67:33). Chemically equivalent bond distances and angles between the two disorder components were restrained to be approximately equal. Additionally, the displacement parameters for all disordered atoms were restrained to be similar to their nearest neighbor, or any atom within 0.7 AÊ. A 1.1 mm colli-mator was used. All H atoms were placed in calculated positions, re®ned using a riding model, and given an isotropic displacement parameter equal to 1.2 times the equivalent isotropic displacement parameter of the atom to which they were attached. The CÐH distances used depended on the type of C atom: CmethyleneÐH =
0.98 AÊ and CareneÐH = 0.94 AÊ.
Data collection:CAD-4-PC(Enraf±Nonius, 1993); cell re®nement:
CAD-4-PC; data reduction:XCAD4 (Harms, 1995); program(s) used to solve structure:SHELXS86 (Sheldrick, 1990); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics:
ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication:PLATON(Spek, 2001).
This research was sponsored by the Division of Chemical Sciences, Geosciences, and Biosciences, Of®ce of Basic Energy Sciences, US Department of Energy, under contract DE-AC05-00OR22725 with Oak Ridge National Laboratory,
Figure 1
References
Bryan, J. C., Sachleben, R. A., Gakh, A. A. & Bunick, G. J. (1999).J. Chem. Crystallogr.29, 513±521.
Bryan, J. C., Lavis, J. M., Hay, B. P. & Sachleben, R. A. (2000).Acta Cryst.C56, 391±392.
Enraf±Nonius (1993). CAD-4-PC. Version 1.2. Enraf±Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Gakh, A. A., Sachleben, R. A. & Bryan, J. C. (1997).CHEMTECH,27(11), 26±33.
Gakh, A. A., Sachleben, R. A., Bryan, J. C. & Moyer, B. A. (1995).
Tetrahedron Lett.45, 8163±8166.
Harms, K. (1995).XCAD4. UniversitaÈt Marburg, Germany. Sheldrick, G. M. (1990).Acta Cryst.A46, 467±473.
Sheldrick, G. M. (1997).SHELXL97. University of GoÈttingen, Germany. Spek, A. L. (2001).PLATON.University of Utrecht, The Netherlands.
supporting information
Acta Cryst. (2002). E58, o129–o131 [https://doi.org/10.1107/S1600536802000302]
(9,10-Triptyceno)benzo-28-crown-8
Jeffrey C. Bryan, Andrei A. Gakh and Richard A. Sachleben
(I)
Crystal data
C40H44O8
Mr = 652.8 Monoclinic, P21/c Hall symbol: -P 2ybc a = 9.3198 (17) Å b = 23.416 (2) Å c = 15.838 (3) Å β = 91.333 (9)° V = 3455.4 (10) Å3
Z = 4
F(000) = 1392 Dx = 1.255 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections θ = 10.1–12.2°
µ = 0.09 mm−1
T = 233 K Plate, colourless 0.63 × 0.50 × 0.04 mm
Data collection
Enraf-Nonius CAD-4 diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
7830 measured reflections 6061 independent reflections 3227 reflections with I > 2σ(I)
Rint = 0.029
θmax = 25.0°, θmin = 2.1°
h = 0→11 k = −16→27 l = −18→18
3 standard reflections every 120 min intensity decay: 2%
Refinement
Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.048
wR(F2) = 0.134
S = 1.01 6061 reflections 487 parameters 51 restraints 0 constraints
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) + (0.061P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.001
Δρmax = 0.27 e Å−3 Δρmin = −0.28 e Å−3
Special details
supporting information
sup-2 Acta Cryst. (2002). E58, o129–o131
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. WeightedR-factorswRand all goodnesses of fitSare based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion ofF2 > σ(F2) is used only for calculating
-R-factor-obsetc. and is not relevant to the choice of reflections for refinement.R-factors based onF2 are statistically about twice as large as those based on F, and
R-factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq Occ. (<1)
O1 0.37625 (17) 0.33879 (7) 0.93471 (10) 0.0460 (6) O2 0.35324 (16) 0.44710 (7) 1.02445 (11) 0.0432 (6) O3 0.09346 (17) 0.47780 (7) 1.11586 (11) 0.0521 (6) O4 −0.15915 (17) 0.46637 (7) 1.22264 (11) 0.0503 (7) O5 −0.27604 (19) 0.36083 (8) 1.21919 (12) 0.0588 (7)
O6 −0.2829 (5) 0.20700 (18) 1.2127 (3) 0.0683 (18) 0.670 O7 −0.2302 (14) 0.0953 (7) 1.1290 (10) 0.065 (3) 0.670 O8 −0.04470 (17) 0.10844 (7) 0.97597 (11) 0.0491 (6)
C33 −0.3686 (3) 0.50313 (13) 1.28521 (18) 0.0590 (11)
C34 −0.3401 (14) 0.3036 (5) 1.2278 (9) 0.050 (3) 0.670 C35 −0.2262 (10) 0.2626 (3) 1.2034 (7) 0.065 (3) 0.670 C36 −0.1791 (6) 0.1658 (2) 1.2317 (3) 0.0711 (19) 0.670 C37 −0.1211 (7) 0.1344 (3) 1.1594 (5) 0.060 (3) 0.670 C38 −0.1757 (4) 0.05180 (12) 1.0711 (2) 0.0701 (13)
C39 −0.1582 (3) 0.06820 (11) 0.98109 (18) 0.0598 (10) C40 −0.0043 (3) 0.11774 (10) 0.89102 (15) 0.0441 (9)
C34A −0.302 (3) 0.3040 (11) 1.219 (2) 0.067 (7) 0.330 C35A −0.1826 (19) 0.2696 (5) 1.1853 (12) 0.049 (5) 0.330 C36A −0.1056 (11) 0.1749 (5) 1.1706 (8) 0.074 (4) 0.330 C37A −0.150 (2) 0.1140 (6) 1.1858 (10) 0.094 (7) 0.330 O7A −0.229 (2) 0.0963 (13) 1.1122 (19) 0.041 (4) 0.330 O6A −0.2251 (9) 0.2120 (4) 1.1810 (6) 0.062 (3) 0.330 H12 −0.26050 0.29140 0.97810 0.0650*
H11 −0.17900 0.20100 0.94410 0.0520*
H17 0.04990 0.11310 0.73150 0.0520*
H18 0.13560 0.13780 0.59950 0.0620*
H19 0.27260 0.21900 0.58380 0.0640*
H20 0.33330 0.27540 0.70030 0.0540*
H21A 0.44490 0.29910 0.83360 0.0520* H13 −0.11450 0.36990 0.96580 0.0630*
H14 0.11760 0.35950 0.91690 0.0500*
H5 0.21380 0.09160 1.00050 0.0570*
H6 0.43510 0.09690 1.07160 0.0740*
H7 0.58400 0.17470 1.05220 0.0730*
H8 0.51280 0.24830 0.96330 0.0560*
H24B 0.33740 0.43850 1.14760 0.0570* H25A 0.23300 0.53250 1.16490 0.0640* H25B 0.21940 0.53530 1.06490 0.0640* H26A −0.04210 0.53070 1.05840 0.0620* H26B −0.01730 0.54400 1.15600 0.0620* H27A −0.24600 0.49960 1.11820 0.0630* H27B −0.15780 0.44280 1.10230 0.0630* H30 −0.53200 0.35960 1.28970 0.0680* H31 −0.65460 0.43740 1.34110 0.0810* H32 −0.55620 0.52750 1.33700 0.0840* H33 −0.32620 0.53960 1.28560 0.0710*
H34A −0.42480 0.29970 1.19040 0.0600* 0.670 H34B −0.36880 0.29690 1.28610 0.0600* 0.670 H35A −0.19910 0.26900 1.14480 0.0780* 0.670 H35B −0.14080 0.26740 1.24000 0.0780* 0.670 H36A −0.22070 0.13800 1.27040 0.0850* 0.670 H36B −0.09910 0.18440 1.26190 0.0850* 0.670 H37A −0.09570 0.16110 1.11460 0.0720* 0.670 H37B −0.03470 0.11330 1.17700 0.0720* 0.670 H38A −0.08210 0.03890 1.09330 0.0500*
supporting information
sup-4 Acta Cryst. (2002). E58, o129–o131
H39A −0.13620 0.03430 0.94750 0.0720* H39B −0.24750 0.08500 0.95860 0.0720* H40A −0.09030 0.12350 0.85530 0.0530* H40B 0.04660 0.08410 0.87020 0.0530* H21B 0.30700 0.33750 0.81620 0.0520* H22A 0.43940 0.41230 0.88710 0.0530* H22B 0.56800 0.37160 0.91580 0.0530* H23A 0.48550 0.38490 1.05940 0.0530* H23B 0.56380 0.43820 1.01890 0.0530* H24A 0.43610 0.49030 1.12060 0.0570*
H34C −0.38840 0.29650 1.18440 0.0800* 0.330 H34D −0.32000 0.29150 1.27640 0.0800* 0.330 H35C −0.15820 0.28320 1.12890 0.0590* 0.330 H35D −0.09750 0.27340 1.22230 0.0590* 0.330 H36C −0.02820 0.18550 1.21050 0.0880* 0.330 H36D −0.06970 0.17880 1.11320 0.0880* 0.330 H37C −0.06550 0.08970 1.19480 0.1130* 0.330 H37D −0.20990 0.11150 1.23580 0.1130* 0.330
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C19 0.0653 (18) 0.0600 (18) 0.0364 (16) 0.0005 (15) 0.0114 (14) 0.0022 (14) C20 0.0477 (15) 0.0426 (15) 0.0451 (16) −0.0049 (12) 0.0113 (13) 0.0041 (13) C21 0.0415 (14) 0.0433 (15) 0.0462 (16) −0.0061 (12) 0.0064 (12) −0.0019 (12) C22 0.0311 (13) 0.0380 (14) 0.0625 (18) −0.0111 (11) 0.0073 (12) −0.0024 (13) C23 0.0270 (13) 0.0413 (15) 0.0638 (19) −0.0043 (11) 0.0004 (12) −0.0011 (13) C24 0.0413 (15) 0.0457 (16) 0.0560 (18) −0.0037 (12) 0.0050 (13) −0.0011 (13) C25 0.0450 (16) 0.0463 (16) 0.068 (2) −0.0052 (14) 0.0121 (14) −0.0052 (14) C26 0.0469 (15) 0.0458 (16) 0.0629 (19) 0.0092 (13) 0.0167 (13) 0.0135 (13) C27 0.0383 (15) 0.0695 (19) 0.0507 (18) 0.0072 (14) 0.0072 (13) 0.0069 (14) C28 0.0333 (14) 0.0506 (17) 0.0478 (16) −0.0027 (13) 0.0082 (12) 0.0042 (13) C29 0.0430 (15) 0.0483 (16) 0.0455 (16) 0.0000 (14) 0.0009 (13) 0.0045 (13) C30 0.0518 (17) 0.0584 (18) 0.0596 (19) −0.0187 (15) 0.0109 (14) 0.0075 (15) C31 0.0555 (19) 0.085 (2) 0.064 (2) −0.0134 (18) 0.0254 (16) −0.0118 (18) C32 0.0555 (19) 0.077 (2) 0.079 (2) −0.0050 (17) 0.0233 (17) −0.0232 (17) C33 0.0504 (17) 0.0569 (19) 0.070 (2) −0.0066 (15) 0.0095 (15) −0.0105 (15) C34 0.040 (6) 0.047 (3) 0.064 (5) −0.004 (3) −0.004 (4) −0.004 (3) C35 0.069 (6) 0.062 (4) 0.065 (6) 0.002 (3) 0.018 (3) 0.004 (3) C36 0.097 (4) 0.055 (3) 0.061 (3) 0.005 (3) −0.007 (3) 0.003 (3) C37 0.055 (3) 0.056 (5) 0.069 (5) 0.009 (3) 0.001 (3) 0.001 (4) C38 0.082 (2) 0.0376 (16) 0.093 (3) −0.0010 (16) 0.0491 (19) 0.0011 (16) C39 0.0637 (18) 0.0431 (16) 0.074 (2) −0.0194 (14) 0.0296 (16) −0.0080 (15) C40 0.0484 (15) 0.0408 (15) 0.0435 (16) −0.0078 (12) 0.0092 (13) 0.0011 (12) C34A 0.032 (12) 0.052 (8) 0.117 (16) −0.012 (7) −0.002 (8) 0.009 (8) C35A 0.075 (11) 0.036 (5) 0.036 (8) −0.007 (5) −0.005 (7) −0.009 (5) C36A 0.087 (8) 0.052 (6) 0.080 (8) 0.007 (5) −0.038 (7) −0.011 (6) C37A 0.143 (15) 0.057 (7) 0.080 (12) 0.003 (8) −0.037 (10) 0.005 (8) O7A 0.031 (6) 0.054 (7) 0.039 (7) −0.002 (5) 0.016 (4) −0.005 (5) O6A 0.067 (6) 0.045 (4) 0.074 (7) −0.013 (4) 0.004 (4) −0.010 (4)
Geometric parameters (Å, º)
O1—C21 1.411 (3) C34A—C35A 1.48 (3)
O1—C22 1.411 (3) C36—C37 1.474 (9)
O2—C23 1.418 (3) C36A—C37A 1.506 (19)
O2—C24 1.412 (3) C38—C39 1.489 (4)
O3—C25 1.412 (3) C5—H5 0.94
O3—C26 1.415 (3) C6—H6 0.94
O4—C27 1.426 (3) C7—H7 0.94
O4—C28 1.384 (3) C8—H8 0.94
O5—C29 1.362 (3) C11—H11 0.94
O5—C34 1.475 (12) C12—H12 0.94
O5—C34A 1.35 (3) C13—H13 0.94
O6—C35 1.414 (9) C14—H14 0.94
O6—C36 1.394 (7) C17—H17 0.94
O6A—C35A 1.407 (15) C18—H18 0.94
O6A—C36A 1.425 (14) C19—H19 0.94
O7—C37 1.443 (16) C20—H20 0.94
supporting information
sup-6 Acta Cryst. (2002). E58, o129–o131
O7A—C38 1.33 (3) C21—H21B 0.98
O7A—C37A 1.43 (3) C22—H22A 0.98
O8—C39 1.420 (3) C22—H22B 0.98
O8—C40 1.422 (3) C23—H23A 0.98
C1—C3 1.528 (3) C23—H23B 0.98
C1—C9 1.542 (3) C24—H24A 0.98
C1—C15 1.536 (3) C24—H24B 0.98
C1—C21 1.509 (3) C25—H25A 0.98
C2—C10 1.537 (3) C25—H25B 0.98
C2—C16 1.542 (3) C26—H26A 0.98
C2—C4 1.535 (3) C26—H26B 0.98
C2—C40 1.511 (3) C27—H27A 0.98
C3—C8 1.387 (3) C27—H27B 0.98
C3—C4 1.400 (3) C30—H30 0.94
C4—C5 1.379 (3) C31—H31 0.94
C5—C6 1.391 (4) C32—H32 0.94
C6—C7 1.378 (4) C33—H33 0.94
C7—C8 1.376 (4) C34—H34A 0.98
C9—C10 1.394 (3) C34—H34B 0.98
C9—C14 1.376 (3) C34A—H34D 0.97
C10—C11 1.390 (3) C34A—H34C 0.98
C11—C12 1.378 (4) C35—H35B 0.98
C12—C13 1.366 (4) C35—H35A 0.98
C13—C14 1.385 (4) C35A—H35C 0.98
C15—C20 1.383 (3) C35A—H35D 0.98
C15—C16 1.398 (3) C36—H36B 0.98
C16—C17 1.379 (3) C36—H36A 0.98
C17—C18 1.388 (4) C36A—H36D 0.98
C18—C19 1.374 (4) C36A—H36C 0.98
C19—C20 1.386 (4) C37—H37A 0.98
C22—C23 1.489 (4) C37—H37B 0.98
C24—C25 1.494 (4) C37A—H37C 0.98
C26—C27 1.494 (4) C37A—H37D 0.98
C28—C29 1.389 (4) C38—H38B 0.98
C28—C33 1.370 (4) C38—H38A 0.98
C29—C30 1.390 (4) C39—H39A 0.98
C30—C31 1.376 (4) C39—H39B 0.98
C31—C32 1.365 (5) C40—H40A 0.98
C32—C33 1.385 (4) C40—H40B 0.98
C34—C35 1.489 (15)
C21—O1—C22 113.47 (18) C20—C19—H19 120
C23—O2—C24 111.13 (19) C15—C20—H20 120
C25—O3—C26 112.36 (19) C19—C20—H20 120
C27—O4—C28 113.36 (19) O1—C21—H21A 110
C29—O5—C34 113.7 (5) O1—C21—H21B 110
C29—O5—C34A 128.4 (12) C1—C21—H21A 110
C35A—O6A—C36A 111.7 (10) H21A—C21—H21B 108
C37—O7—C38 113.4 (9) O1—C22—H22A 110
C37A—O7A—C38 115.8 (18) O1—C22—H22B 110
C39—O8—C40 111.68 (19) C23—C22—H22A 110
C3—C1—C9 105.41 (17) C23—C22—H22B 110
C9—C1—C15 104.58 (15) H22A—C22—H22B 108
C3—C1—C15 104.88 (17) O2—C23—H23A 110
C3—C1—C21 114.69 (17) O2—C23—H23B 110
C15—C1—C21 112.27 (18) C22—C23—H23A 110
C9—C1—C21 114.05 (18) C22—C23—H23B 110
C4—C2—C40 115.66 (18) H23A—C23—H23B 108
C10—C2—C16 104.59 (17) O2—C24—H24A 110
C10—C2—C40 114.84 (17) O2—C24—H24B 110
C16—C2—C40 111.08 (18) C25—C24—H24A 110
C4—C2—C10 104.83 (17) C25—C24—H24B 110
C4—C2—C16 104.77 (15) H24A—C24—H24B 108
C1—C3—C8 126.29 (19) O3—C25—H25A 110
C1—C3—C4 114.03 (17) O3—C25—H25B 110
C4—C3—C8 119.7 (2) C24—C25—H25A 110
C2—C4—C5 126.6 (2) C24—C25—H25B 110
C3—C4—C5 119.9 (2) H25A—C25—H25B 108
C2—C4—C3 113.57 (18) O3—C26—H26A 110
C4—C5—C6 119.8 (2) O3—C26—H26B 110
C5—C6—C7 120.3 (3) C27—C26—H26A 110
C6—C7—C8 120.3 (3) C27—C26—H26B 110
C3—C8—C7 120.1 (2) H26A—C26—H26B 108
C10—C9—C14 120.3 (2) O4—C27—H27A 110
C1—C9—C14 126.4 (2) O4—C27—H27B 110
C1—C9—C10 113.29 (18) C26—C27—H27A 110
C2—C10—C9 114.31 (17) C26—C27—H27B 110
C2—C10—C11 126.1 (2) H27A—C27—H27B 108
C9—C10—C11 119.6 (2) C29—C30—H30 120
C10—C11—C12 119.2 (2) C31—C30—H30 120
C11—C12—C13 121.2 (2) C30—C31—H31 119
C12—C13—C14 120.1 (2) C32—C31—H31 119
C9—C14—C13 119.7 (2) C31—C32—H32 120
C1—C15—C16 113.73 (19) C33—C32—H32 120
C1—C15—C20 126.1 (2) C28—C33—H33 120
C16—C15—C20 120.1 (2) C32—C33—H33 120
C2—C16—C15 113.70 (19) O5—C34—H34A 111
C15—C16—C17 120.0 (2) O5—C34—H34B 111
C2—C16—C17 126.3 (2) C35—C34—H34A 111
C16—C17—C18 119.6 (2) C35—C34—H34B 111
C17—C18—C19 120.3 (2) H34A—C34—H34B 109
C18—C19—C20 120.7 (2) C35A—C34A—H34C 108
C15—C20—C19 119.3 (2) O5—C34A—H34C 109
O1—C21—C1 109.53 (19) O5—C34A—H34D 109
supporting information
sup-8 Acta Cryst. (2002). E58, o129–o131
O2—C23—C22 109.29 (18) H34C—C34A—H34D 108
O2—C24—C25 110.3 (2) O6—C35—H35A 110
O3—C25—C24 109.8 (2) H35A—C35—H35B 109
O3—C26—C27 109.5 (2) O6—C35—H35B 110
O4—C27—C26 109.7 (2) C34—C35—H35A 110
C29—C28—C33 120.3 (3) C34—C35—H35B 110
O4—C28—C29 120.8 (2) O6A—C35A—H35D 110
O4—C28—C33 118.9 (2) C34A—C35A—H35C 110
C28—C29—C30 118.8 (2) C34A—C35A—H35D 110
O5—C29—C30 124.9 (2) O6A—C35A—H35C 110
O5—C29—C28 116.3 (2) H35C—C35A—H35D 108
C29—C30—C31 119.9 (3) O6—C36—H36B 108
C30—C31—C32 121.2 (3) C37—C36—H36A 108
C31—C32—C33 119.1 (3) O6—C36—H36A 108
C28—C33—C32 120.6 (3) H36A—C36—H36B 107
O5—C34—C35 105.6 (9) C37—C36—H36B 108
O5—C34A—C35A 114 (2) O6A—C36A—H36D 110
O6—C35—C34 107.2 (8) C37A—C36A—H36C 110
O6A—C35A—C34A 109.0 (15) H36C—C36A—H36D 108
O6—C36—C37 116.3 (5) C37A—C36A—H36D 110
O6A—C36A—C37A 109.9 (10) O6A—C36A—H36C 110
O7—C37—C36 107.9 (8) H37A—C37—H37B 109
O7A—C37A—C36A 106.5 (16) O7—C37—H37A 110
O7—C38—C39 117.8 (7) O7—C37—H37B 110
O7A—C38—C39 108.5 (13) C36—C37—H37A 110
O8—C39—C38 108.9 (2) C36—C37—H37B 110
O8—C40—C2 110.16 (19) O7A—C37A—H37C 110
C4—C5—H5 120 C36A—C37A—H37D 110
C6—C5—H5 120 O7A—C37A—H37D 110
C5—C6—H6 120 C36A—C37A—H37C 111
C7—C6—H6 120 H37C—C37A—H37D 109
C6—C7—H7 120 O7—C38—H38A 108
C8—C7—H7 120 O7A—C38—H38B 111
C3—C8—H8 120 O7A—C38—H38A 114
C7—C8—H8 120 C39—C38—H38A 108
C10—C11—H11 120 C39—C38—H38B 108
C12—C11—H11 120 O7—C38—H38B 108
C11—C12—H12 119 H38A—C38—H38B 107
C13—C12—H12 119 O8—C39—H39B 110
C12—C13—H13 120 C38—C39—H39A 110
C14—C13—H13 120 O8—C39—H39A 110
C9—C14—H14 120 H39A—C39—H39B 108
C13—C14—H14 120 C38—C39—H39B 110
C16—C17—H17 120 H40A—C40—H40B 108
C18—C17—H17 120 C2—C40—H40B 110
C17—C18—H18 120 O8—C40—H40A 110
C19—C18—H18 120 O8—C40—H40B 110
supporting information
sup-10 Acta Cryst. (2002). E58, o129–o131
C10—C2—C40—O8 −63.5 (3) O5—C29—C30—C31 −178.4 (3) C16—C2—C40—O8 178.11 (17) C28—C29—C30—C31 2.0 (4) C4—C2—C16—C17 124.4 (2) C29—C30—C31—C32 −0.7 (4) C10—C2—C16—C15 54.2 (2) C30—C31—C32—C33 −1.4 (5) C16—C2—C10—C9 −55.4 (2) C31—C32—C33—C28 2.1 (4) C16—C2—C10—C11 123.8 (2) O5—C34—C35—O6 178.7 (8) C40—C2—C10—C9 −177.42 (19) O6—C36—C37—O7 −73.0 (9) C40—C2—C10—C11 1.8 (3) O7—C38—C39—O8 68.5 (7)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C5—H5···O8 0.94 2.46 2.994 (3) 116
C8—H8···O1 0.94 2.51 2.995 (3) 113
C11—H11···O8 0.94 2.55 3.047 (3) 114
C14—H14···O1 0.94 2.47 2.978 (3) 114
