organic papers
o1964
Watcharee Waratchareeyakulet al. C26H30O6 doi: 10.1107/S160053680402450X Acta Cryst.(2004). E60, o1964±o1966 Acta Crystallographica Section EStructure Reports
Online ISSN 1600-5368
7-Oxogedunin
Watcharee Waratchareeyakul,a
Suchada Chantrapromma,a*
Hoong-Kun Fun,bIbrahim Abdul
Razak,bChatchanok Karalaiaand
Chanita Ponglimanonta
aDepartment of Chemistry, Faculty of Science,
Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, andbX-ray Crystallography
Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: [email protected]
Key indicators Single-crystal X-ray study T= 293 K
Mean(C±C) = 0.005 AÊ Rfactor = 0.047 wRfactor = 0.110 Data-to-parameter ratio = 7.9
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved
The title compound, 1-(3-furyl)-4b,7,7,10a,12a-pentamethyl-1,6a,7,10a,10b,11,12,12a-octahydronaphtho[2,1-f
]oxireno[2,3-d]isochromene-3,5,8(3aH,4bH,6H)-trione, C26H30O6, has
been isolated from Xylocarpus granatum Koenig. All four
rings are trans-fused. The four six-membered rings adopt
distorted sofa, chair, twist-boat and half-chair conformations. The furan substituent is planar and attached equatorially to the lactone ring of the gedunin skeleton. The crystal structure is stabilized by CÐH O intramolecular and intermolecular interactions.
Comment
Xylocarpus granatum Koenig is a mangrove plant from the family Meliaceae, growing around the littoral of the tropical Indian ocean and extending to the Paci®c islands. Limonoids from this plant have been reported to exhibit important biological activities such as antimalarial (MacKinnon et al.,
1997) and insect antifeedant (Champagne et al., 1992),
whereas the aqueous extract showed signi®cant anti®larial activity (Zaridah et al., 2001). The title compound, 7-oxoge-dunin, (I), was previously isolated from various genera of the Meliaceae family, such as Guarea Guidona(Lukacova et al., 1982), Xylocarpus moluccenis (Mulholland & Taylor, 1992) andCedrela Odorata(Paulaet al., 1997). It was found not to possess antitubercular, antimalarial or antitumor activities.
The title compound was isolated from the seeds of
Xylo-carpus granatumKoenig, which were collected from Nakhon-Si-Thammarat province in southern Thailand. As part of our research on bioactive constituents from Thai mangrove plants (Chantraprommaet al., 2003; Funet al., 2003; Cheenprachaet al., 2004), we report here the crystal structure of (I). The results will be useful for molecular modeling and biotrans-formation studies, which are the current interests of our research group. Although the title compound has no activity, a modi®cation of its molecular structure to induce antimalarial activity and cytotoxicity will be under investigation.
The structure of (I) contains a four-ring A/B/C/D fused triterpenoid system, known as the gedunin skeleton (Fig. 1). The A/B, B/C and C/D ring junctions are trans-fused. The bond lengths and angles in (I) show normal values (Allen et al., 1987) and are comparable with the corresponding values in the related compounds mexicanolide (Sanniet al., 1987) and
6-hydroxymexicanolide (Chantrapromma et al., 2004). The
crystal structure of gedunin itself has been reported earlier (Toscanoet al., 1996).
The conformations adopted by rings A, B, C and D are
distorted sofa, approximate chair, twist-boat and half-chair, respectively (Cremer & Pople, 1975). The distorted sofa conformation is induced by the,-unsaturated ketone func-tion of ringA. The methyl groups are attached axially to rings
A, BandCat atoms C1, C5, C9 and C13. The furan ring is
planar to within 0.007 (4) AÊ and is attached equatorially to lactone ring D, the torsion angle C13ÐC17ÐC18ÐC21 being 89.2 (4). The conformations of the carbonyl groups C4 O1,
C8 O2 and C16 O5 are: (ÿ)-synclinal with O1ÐC4ÐC5Ð
C22 = ÿ63.7 (5), (ÿ)-anticlinal with O2ÐC8ÐC9ÐC25 =
ÿ116.2 (4) and (+)-anticlinal with O3ÐC15ÐC16ÐO5 =
137.5 (4).
The crystal structure is stabilized by CÐH O intra- and intermolecular interactions (Table 2). The latter link mol-ecules together, forming a molecular chain along the aaxis (Fig. 2).
Experimental
Air-dried seeds of Xylocarpus granatum Koeing (5.2 kg) were extracted with hexane, CH2Cl2 and MeOH, successively. The
di-chloromethane extract was dried under reduced pressure to yield a crude extract (68.67 g). The crude extract (26.14 g) was separated by fast column chromatography on silica gel and eluted initially with hexane enriched with ethyl acetate, followed by an increasing amount of methanol in ethyl acetate and ®nally with methanol. Each fraction was monitored by thin-layer chromatography; fractions that appeared similar were combined to yield 20 major fractions, denoted F1±F20. Fraction F5 (0.41 g) was further puri®ed by crystallization to give (I) (0.25 g). Compound (I) was recrystallized from hexane±CH2Cl2±
EtOAc (4:4:2) to give colorless single crystals after a few days (m.p. 533±535 K).
Crystal data C26H30O6
Mr= 438.50 Monoclinic,P21
a= 7.6623 (12) AÊ
b= 11.1298 (18) AÊ
c= 13.350 (2) AÊ
= 100.547 (3)
V= 1119.2 (3) AÊ3
Z= 2
Dx= 1.301 Mg mÿ3 MoKradiation Cell parameters from 3780
re¯ections
= 1.6±28.3 = 0.09 mmÿ1
T= 293 (2) K Plate, colorless 0.250.190.08 mm Data collection
Siemens SMART CCD area detector diffractometer
!scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)
Tmin= 0.977,Tmax= 0.993 8802 measured re¯ections
2330 independent re¯ections 2052 re¯ections withI> 2(I)
Rint= 0.031
max= 26.0
h=ÿ9!9
k=ÿ13!13
l=ÿ16!16 Refinement
Re®nement onF2
R[F2> 2(F2)] = 0.047
wR(F2) = 0.110
S= 1.11 2330 re¯ections 294 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0538P)2 + 0.1209P]
whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001
max= 0.19 e AÊÿ3
min=ÿ0.22 e AÊÿ3
Table 1
Selected geometric parameters (AÊ,). O1ÐC4 1.210 (4) O2ÐC8 1.211 (4) O5ÐC16 1.195 (4) O3ÐC15 1.431 (4) O3ÐC14 1.453 (4) O4ÐC16 1.340 (4) O4ÐC17 1.464 (4)
O6ÐC20 1.349 (6) O6ÐC21 1.357 (5) C2ÐC3 1.318 (5) C18ÐC21 1.341 (5) C18ÐC19 1.422 (5) C19ÐC20 1.330 (6)
C15ÐO3ÐC14 61.4 (2)
C16ÐO4ÐC17 121.1 (2) C23ÐC5ÐC22 108.1 (3) O1ÐC4ÐC5ÐC22 ÿ63.7 (5)
O1ÐC4ÐC5ÐC6 171.5 (4) O2ÐC8ÐC9ÐC25 ÿ116.2 (4) O2ÐC8ÐC9ÐC10 120.4 (4)
O3ÐC15ÐC16ÐO5 137.5 (4) C14ÐC15ÐC16ÐO5 ÿ153.4 (3) C13ÐC17ÐC18ÐC21 89.2 (4)
organic papers
Acta Cryst.(2004). E60, o1964±o1966 Watcharee Waratchareeyakulet al. C26H30O6
o1965
Figure 1The structure of the title compound, showing 50% probability displace-ment ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
Figure 2
Table 2
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
C11ÐH11B O2i 0.97 2.35 3.288 (4) 162 C21ÐH21A O5i 0.93 2.43 3.361 (5) 176 C23ÐH23A O1 0.96 2.50 2.846 (6) 101 Symmetry code: (i)xÿ1;y;z.
H atoms were placed in calculated positions, with CÐH distances in the range 0.93±0.98 AÊ. The Uiso values were constrained to be
1.5Ueqof the carrier atom for methyl H atoms and 1.2Ueqfor the
remaining H atoms. In the absence of signi®cant anomalous disper-sion effects, Friedel pairs were merged before the ®nal re®nement. Owing to a large fraction of weak data at higher angles, the 2
maximum was limited to 52.
Data collection:SMART(Siemens, 1996); cell re®nement:SAINT
(Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to re®ne structure:SHELXTL; molecular graphics:SHELXTL; software used to prepare material for publication:SHELXTLandPLATON(Spek, 2003).
WW thanks the Higher Education Development Project: Postgraduate Education and Research Program in Chemistry for ®nancial support and data collection. The authors thank Prince of Songkla University and also the Malaysian
Government and Universiti Sains Malaysia for research grant R&D No. 304/PFIZIK/635028.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987).J. Chem. Soc. Perkin Trans.2, pp. S1±19.
Champagne, D. E., Koul, O., Isman, M. B., Scudder, G. E. & Towers, G. H. N. (1992).Phytochemistry,31, 377±394.
Chantrapromma, S., Fun, H.-K., Ibrahim A. R., Laphookhieo, S. & Karalai, C. (2003).Acta Cryst.E59, o1864±o1866.
Chantrapromma, K., Saewan, N., Fun, H.-K., Chantrapromma, S. & Rahman, A. A. (2004).Acta Cryst.E60, o312±o314.
Cheenpracha, S. Karalai, C., Rat-A-Pa, Y., Ponglimanont, C. & Chantra-promma, K. (2004).Chem. Pharm. Bull.52, 1023±1025.
Cremer, D. & Pople, J. A. (1975).J. Am. Chem. Soc.97, 1354±1358. Fun, H.-K., Chantrapromma, S., Cheenpracha, S., Karalai, C., Anjum, S.,
Chantrapromma, K. & Rahman, A. A. (2003).Acta Cryst.E59, o1694± o1696.
Lukacova, V., Polonsky, J. & Moretti, C. (1982).J. Nat. Prod.45, 287±294. MacKinnon, S., Durst, T. & Arnason, J. T. (1997).J. Nat. Prod.60, 336±341. Mulholland, D. A. & Taylor, D. A. H. (1992).Phytochemistry,31, 4163±4166. Paula, J. R., Vieira, I. J. V., Silva, M. F. G. F., Fo, E. R., Fernandes, J. B., Vieira, P. C., Pinheiro, A. L. & Vilela, E. F. (1997).Phytochemistry,44, 1449±1454. Sanni, S. B., Behm, H. & Beurskens, P. T. (1987).Acta Cryst.C43, 1400±1403. Sheldrick, G. M. (1996).SADABS.University of GoÈttingen, Germany. Sheldrick, G. M. (1997).SHELXTL.Version 5.1. Bruker AXS Inc., Madison,
Wisconsin, USA.
Siemens (1996).SMARTandSAINT.Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Spek, A. L. (2003).J. Appl. Cryst.36, 7±13.
Toscano, R. A., Mata, R., Calderon, J. & Segura, R. (1996). J. Chem. Crystallogr.26, 707±711.
Zaridah, M. Z., Idid, S. Z., Omar, A. W. & Khozirah, S. (2001). J. Ethnopharmacol.78, 79±84.
organic papers
supporting information
sup-1 Acta Cryst. (2004). E60, o1964–o1966
supporting information
Acta Cryst. (2004). E60, o1964–o1966 [https://doi.org/10.1107/S160053680402450X]
7-Oxogedunin
Watcharee Waratchareeyakul, Suchada Chantrapromma, Hoong-Kun Fun, Ibrahim Abdul
Razak, Chatchanok Karalai and Chanita Ponglimanont
1-(3-furyl)-4 b,7,7,10a,12a-pentamethyl-1,6a,7,10a,10b,11,12,12a- octahydronaphtho[2,1-f
]oxireno[2,3-d]isochromene-3,5,8(3aH,4bH,6H)-trione
Crystal data
C26H30O6 Mr = 438.50
Monoclinic, P21 a = 7.6623 (12) Å b = 11.1298 (18) Å c = 13.350 (2) Å β = 100.547 (3)° V = 1119.2 (3) Å3 Z = 2
F(000) = 468
Dx = 1.301 Mg m−3
Melting point = 533–535 K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 3780 reflections θ = 1.6–28.3°
µ = 0.09 mm−1 T = 293 K Plate, colorless 0.25 × 0.19 × 0.08 mm
Data collection
Siemens SMART CCD area detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
Detector resolution: 8.33 pixels mm-1 ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.977, Tmax = 0.993
8802 measured reflections 2330 independent reflections 2052 reflections with I > 2σ(I) Rint = 0.031
θmax = 26.0°, θmin = 1.6° h = −9→9
k = −13→13 l = −16→16
Refinement
Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.047 wR(F2) = 0.110 S = 1.11 2330 reflections 294 parameters 1 restraint
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) + (0.0538P)2 + 0.1209P] where P = (Fo2 + 2Fc2)/3
supporting information
sup-2 Acta Cryst. (2004). E60, o1964–o1966
Special details
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
O1 0.1781 (4) 0.1681 (3) 1.0009 (2) 0.0918 (11)
O2 0.5747 (3) 0.4522 (3) 0.64031 (19) 0.0640 (8)
O5 0.5713 (3) 0.6475 (3) 0.36168 (19) 0.0621 (7)
O3 0.2527 (3) 0.7087 (2) 0.51167 (18) 0.0485 (6)
O4 0.2930 (3) 0.5894 (2) 0.32426 (17) 0.0486 (6)
O6 −0.2004 (4) 0.4147 (3) 0.1606 (2) 0.0780 (10)
C1 0.1490 (4) 0.4382 (3) 0.7851 (2) 0.0336 (7)
C2 0.0036 (4) 0.3460 (3) 0.7886 (2) 0.0418 (8)
H2A −0.1019 0.3527 0.7418 0.050*
C3 0.0204 (5) 0.2571 (3) 0.8548 (3) 0.0484 (9)
H3A −0.0748 0.2048 0.8532 0.058*
C4 0.1809 (5) 0.2364 (3) 0.9307 (3) 0.0538 (9)
C5 0.3512 (5) 0.3044 (3) 0.9224 (2) 0.0460 (8)
C6 0.3259 (4) 0.3696 (3) 0.8180 (2) 0.0371 (7)
H6A 0.3199 0.3042 0.7683 0.045*
C7 0.4893 (4) 0.4431 (4) 0.8028 (3) 0.0528 (9)
H7A 0.5012 0.5131 0.8468 0.063*
H7B 0.5955 0.3947 0.8211 0.063*
C8 0.4699 (4) 0.4825 (4) 0.6933 (3) 0.0454 (9)
C9 0.3050 (4) 0.5563 (3) 0.6543 (2) 0.0359 (7)
C10 0.1448 (3) 0.4753 (3) 0.6729 (2) 0.0308 (6)
H10A 0.1614 0.3996 0.6383 0.037*
C11 −0.0236 (4) 0.5286 (3) 0.6100 (2) 0.0444 (8)
H11A −0.0237 0.6152 0.6184 0.053*
H11B −0.1272 0.4963 0.6327 0.053*
C12 −0.0299 (4) 0.4971 (3) 0.4978 (3) 0.0436 (8)
H12A −0.1107 0.5520 0.4560 0.052*
H12B −0.0775 0.4166 0.4855 0.052*
C13 0.1535 (4) 0.5029 (3) 0.4636 (2) 0.0326 (6)
C14 0.2766 (4) 0.5824 (3) 0.5383 (2) 0.0342 (7)
C15 0.4123 (4) 0.6502 (3) 0.4967 (3) 0.0453 (8)
H15A 0.5203 0.6709 0.5452 0.054*
C16 0.4339 (4) 0.6307 (3) 0.3897 (3) 0.0448 (8)
C17 0.1252 (4) 0.5634 (3) 0.3577 (2) 0.0399 (7)
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sup-3 Acta Cryst. (2004). E60, o1964–o1966
C18 0.0223 (4) 0.4901 (3) 0.2732 (2) 0.0443 (8)
C19 0.0916 (6) 0.4112 (4) 0.2063 (3) 0.0662 (11)
H19A 0.2103 0.3919 0.2085 0.079*
C20 −0.0468 (8) 0.3705 (5) 0.1401 (3) 0.0748 (13)
H20A −0.0388 0.3184 0.0867 0.090*
C21 −0.1544 (5) 0.4886 (4) 0.2420 (3) 0.0574 (10)
H21A −0.2344 0.5323 0.2721 0.069*
C22 0.3961 (6) 0.3883 (4) 1.0151 (3) 0.0642 (11)
H22A 0.4106 0.3417 1.0766 0.096*
H22B 0.3015 0.4451 1.0143 0.096*
H22C 0.5043 0.4306 1.0122 0.096*
C23 0.5000 (6) 0.2108 (5) 0.9290 (3) 0.0732 (12)
H23A 0.4982 0.1591 0.9864 0.110*
H23B 0.6126 0.2510 0.9371 0.110*
H23C 0.4823 0.1639 0.8677 0.110*
C24 0.1085 (5) 0.5429 (4) 0.8538 (3) 0.0530 (9)
H24A 0.0198 0.5943 0.8157 0.079*
H24B 0.2149 0.5882 0.8767 0.079*
H24C 0.0657 0.5110 0.9117 0.079*
C25 0.3216 (6) 0.6778 (3) 0.7107 (3) 0.0587 (10)
H25A 0.4090 0.7265 0.6869 0.088*
H25B 0.3570 0.6643 0.7826 0.088*
H25C 0.2091 0.7183 0.6978 0.088*
C26 0.2393 (5) 0.3790 (3) 0.4574 (2) 0.0438 (8)
H26A 0.3440 0.3874 0.4280 0.066*
H26B 0.1567 0.3267 0.4156 0.066*
H26C 0.2706 0.3456 0.5245 0.066*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O1 0.110 (2) 0.094 (3) 0.0705 (19) −0.023 (2) 0.0160 (17) 0.040 (2)
O2 0.0319 (12) 0.102 (2) 0.0614 (16) 0.0095 (14) 0.0169 (12) 0.0213 (16)
O5 0.0501 (14) 0.0780 (19) 0.0634 (17) −0.0167 (14) 0.0247 (12) 0.0089 (15)
O3 0.0663 (15) 0.0293 (12) 0.0528 (14) −0.0011 (11) 0.0190 (12) 0.0026 (11)
O4 0.0474 (13) 0.0593 (16) 0.0405 (13) −0.0092 (12) 0.0122 (10) 0.0064 (11)
O6 0.080 (2) 0.089 (2) 0.0566 (18) −0.0281 (19) −0.0088 (15) 0.0046 (17)
C1 0.0335 (15) 0.0342 (15) 0.0353 (15) 0.0001 (13) 0.0120 (12) −0.0038 (13)
C2 0.0386 (18) 0.050 (2) 0.0392 (17) −0.0049 (15) 0.0147 (14) −0.0037 (16)
C3 0.055 (2) 0.049 (2) 0.047 (2) −0.0187 (17) 0.0235 (17) −0.0053 (17)
C4 0.076 (3) 0.045 (2) 0.0430 (19) −0.0054 (19) 0.0179 (18) 0.0047 (17)
C5 0.053 (2) 0.051 (2) 0.0330 (17) 0.0027 (17) 0.0057 (15) 0.0053 (15)
C6 0.0361 (17) 0.0392 (17) 0.0365 (16) 0.0007 (14) 0.0077 (13) −0.0017 (14)
C7 0.0368 (18) 0.074 (3) 0.0456 (19) −0.0034 (18) 0.0015 (14) 0.0102 (19)
C8 0.0249 (15) 0.062 (2) 0.0490 (19) −0.0151 (15) 0.0050 (14) 0.0057 (17)
C9 0.0344 (16) 0.0349 (17) 0.0400 (17) −0.0066 (13) 0.0106 (13) −0.0007 (14)
C10 0.0267 (14) 0.0316 (16) 0.0356 (15) 0.0018 (12) 0.0093 (12) −0.0012 (12)
supporting information
sup-4 Acta Cryst. (2004). E60, o1964–o1966
C12 0.0299 (17) 0.053 (2) 0.0463 (18) 0.0005 (15) 0.0042 (13) 0.0118 (16)
C13 0.0320 (15) 0.0308 (15) 0.0347 (15) 0.0002 (13) 0.0051 (12) 0.0025 (13)
C14 0.0341 (16) 0.0293 (16) 0.0400 (17) 0.0027 (13) 0.0087 (13) 0.0027 (14)
C15 0.0450 (18) 0.0440 (19) 0.0474 (19) −0.0151 (16) 0.0092 (15) 0.0049 (16)
C16 0.046 (2) 0.0406 (19) 0.049 (2) −0.0060 (15) 0.0116 (16) 0.0112 (16)
C17 0.0345 (16) 0.0439 (18) 0.0420 (17) 0.0019 (15) 0.0092 (13) 0.0075 (15)
C18 0.051 (2) 0.0437 (19) 0.0367 (17) −0.0012 (16) 0.0046 (15) 0.0097 (15)
C19 0.077 (3) 0.075 (3) 0.048 (2) −0.003 (2) 0.013 (2) −0.005 (2)
C20 0.104 (4) 0.071 (3) 0.048 (2) −0.015 (3) 0.010 (2) −0.010 (2)
C21 0.057 (2) 0.063 (3) 0.049 (2) −0.004 (2) 0.0003 (17) 0.0036 (19)
C22 0.074 (3) 0.079 (3) 0.0351 (18) −0.002 (2) −0.0014 (18) 0.001 (2)
C23 0.079 (3) 0.076 (3) 0.062 (2) 0.022 (3) 0.006 (2) 0.021 (2)
C24 0.062 (2) 0.050 (2) 0.052 (2) 0.0065 (18) 0.0248 (18) −0.0042 (18)
C25 0.082 (3) 0.049 (2) 0.046 (2) −0.024 (2) 0.0169 (19) −0.0066 (18)
C26 0.051 (2) 0.0404 (19) 0.0398 (18) 0.0012 (16) 0.0091 (15) −0.0004 (15)
Geometric parameters (Å, º)
O1—C4 1.210 (4) C11—H11B 0.9700
O2—C8 1.211 (4) C12—C13 1.556 (4)
O5—C16 1.195 (4) C12—H12A 0.9700
O3—C15 1.431 (4) C12—H12B 0.9700
O3—C14 1.453 (4) C13—C14 1.523 (4)
O4—C16 1.340 (4) C13—C26 1.536 (4)
O4—C17 1.464 (4) C13—C17 1.545 (4)
O6—C20 1.349 (6) C14—C15 1.473 (4)
O6—C21 1.357 (5) C15—C16 1.483 (5)
C1—C2 1.522 (4) C15—H15A 0.9800
C1—C6 1.548 (4) C17—C18 1.495 (5)
C1—C10 1.548 (4) C17—H17A 0.9800
C1—C24 1.550 (5) C18—C21 1.341 (5)
C2—C3 1.318 (5) C18—C19 1.422 (5)
C2—H2A 0.9300 C19—C20 1.330 (6)
C3—C4 1.462 (5) C19—H19A 0.9300
C3—H3A 0.9300 C20—H20A 0.9300
C4—C5 1.529 (5) C21—H21A 0.9300
C5—C23 1.535 (6) C22—H22A 0.9600
C5—C22 1.538 (5) C22—H22B 0.9600
C5—C6 1.552 (4) C22—H22C 0.9600
C6—C7 1.540 (5) C23—H23A 0.9600
C6—H6A 0.9800 C23—H23B 0.9600
C7—C8 1.507 (5) C23—H23C 0.9600
C7—H7A 0.9700 C24—H24A 0.9600
C7—H7B 0.9700 C24—H24B 0.9600
C8—C9 1.517 (5) C24—H24C 0.9600
C9—C25 1.542 (5) C25—H25A 0.9600
C9—C14 1.552 (4) C25—H25B 0.9600
supporting information
sup-5 Acta Cryst. (2004). E60, o1964–o1966
C10—C11 1.525 (4) C26—H26A 0.9600
C10—H10A 0.9800 C26—H26B 0.9600
C11—C12 1.530 (5) C26—H26C 0.9600
C11—H11A 0.9700
C15—O3—C14 61.4 (2) C14—C13—C12 108.5 (2)
C16—O4—C17 121.1 (2) C26—C13—C12 113.4 (3)
C20—O6—C21 106.0 (3) C17—C13—C12 107.7 (2)
C2—C1—C6 105.4 (3) O3—C14—C15 58.6 (2)
C2—C1—C10 108.9 (2) O3—C14—C13 111.5 (2)
C6—C1—C10 105.6 (2) C15—C14—C13 116.5 (3)
C2—C1—C24 105.2 (2) O3—C14—C9 114.5 (2)
C6—C1—C24 117.6 (3) C15—C14—C9 119.5 (3)
C10—C1—C24 113.7 (3) C13—C14—C9 120.0 (2)
C3—C2—C1 123.0 (3) O3—C15—C14 60.00 (19)
C3—C2—H2A 118.5 O3—C15—C16 116.7 (3)
C1—C2—H2A 118.5 C14—C15—C16 119.9 (3)
C2—C3—C4 123.4 (3) O3—C15—H15A 116.1
C2—C3—H3A 118.3 C14—C15—H15A 116.1
C4—C3—H3A 118.3 C16—C15—H15A 116.1
O1—C4—C3 120.2 (4) O5—C16—O4 120.0 (3)
O1—C4—C5 120.2 (4) O5—C16—C15 122.6 (3)
C3—C4—C5 119.5 (3) O4—C16—C15 117.4 (3)
C4—C5—C23 107.2 (3) O4—C17—C18 104.4 (2)
C4—C5—C22 108.1 (3) O4—C17—C13 112.4 (2)
C23—C5—C22 108.1 (3) C18—C17—C13 114.8 (3)
C4—C5—C6 109.2 (3) O4—C17—H17A 108.3
C23—C5—C6 109.8 (3) C18—C17—H17A 108.3
C22—C5—C6 114.3 (3) C13—C17—H17A 108.3
C7—C6—C1 113.0 (3) C21—C18—C19 105.6 (4)
C7—C6—C5 113.4 (3) C21—C18—C17 127.1 (3)
C1—C6—C5 116.4 (2) C19—C18—C17 127.2 (3)
C7—C6—H6A 104.1 C20—C19—C18 106.5 (4)
C1—C6—H6A 104.1 C20—C19—H19A 126.8
C5—C6—H6A 104.1 C18—C19—H19A 126.8
C8—C7—C6 110.2 (3) C19—C20—O6 111.1 (4)
C8—C7—H7A 109.6 C19—C20—H20A 124.5
C6—C7—H7A 109.6 O6—C20—H20A 124.5
C8—C7—H7B 109.6 C18—C21—O6 110.8 (4)
C6—C7—H7B 109.6 C18—C21—H21A 124.6
H7A—C7—H7B 108.1 O6—C21—H21A 124.6
O2—C8—C7 121.8 (3) C5—C22—H22A 109.5
O2—C8—C9 123.4 (3) C5—C22—H22B 109.5
C7—C8—C9 114.7 (3) H22A—C22—H22B 109.5
C8—C9—C25 108.6 (3) C5—C22—H22C 109.5
C8—C9—C14 113.5 (2) H22A—C22—H22C 109.5
C25—C9—C14 107.8 (3) H22B—C22—H22C 109.5
supporting information
sup-6 Acta Cryst. (2004). E60, o1964–o1966
C25—C9—C10 114.9 (3) C5—C23—H23B 109.5
C14—C9—C10 107.0 (2) H23A—C23—H23B 109.5
C11—C10—C1 120.2 (2) C5—C23—H23C 109.5
C11—C10—C9 107.2 (3) H23A—C23—H23C 109.5
C1—C10—C9 115.1 (2) H23B—C23—H23C 109.5
C11—C10—H10A 104.2 C1—C24—H24A 109.5
C1—C10—H10A 104.2 C1—C24—H24B 109.5
C9—C10—H10A 104.2 H24A—C24—H24B 109.5
C10—C11—C12 108.8 (3) C1—C24—H24C 109.5
C10—C11—H11A 109.9 H24A—C24—H24C 109.5
C12—C11—H11A 109.9 H24B—C24—H24C 109.5
C10—C11—H11B 109.9 C9—C25—H25A 109.5
C12—C11—H11B 109.9 C9—C25—H25B 109.5
H11A—C11—H11B 108.3 H25A—C25—H25B 109.5
C11—C12—C13 114.1 (3) C9—C25—H25C 109.5
C11—C12—H12A 108.7 H25A—C25—H25C 109.5
C13—C12—H12A 108.7 H25B—C25—H25C 109.5
C11—C12—H12B 108.7 C13—C26—H26A 109.5
C13—C12—H12B 108.7 C13—C26—H26B 109.5
H12A—C12—H12B 107.6 H26A—C26—H26B 109.5
C14—C13—C26 109.7 (2) C13—C26—H26C 109.5
C14—C13—C17 108.2 (2) H26A—C26—H26C 109.5
C26—C13—C17 109.3 (2) H26B—C26—H26C 109.5
C6—C1—C2—C3 32.8 (4) C15—O3—C14—C13 −108.7 (3)
C10—C1—C2—C3 145.7 (3) C15—O3—C14—C9 110.9 (3)
C24—C1—C2—C3 −92.1 (4) C26—C13—C14—O3 151.2 (2)
C1—C2—C3—C4 −1.0 (5) C17—C13—C14—O3 32.0 (3)
C2—C3—C4—O1 166.4 (4) C12—C13—C14—O3 −84.5 (3)
C2—C3—C4—C5 −11.9 (5) C26—C13—C14—C15 86.6 (3)
O1—C4—C5—C23 52.6 (5) C17—C13—C14—C15 −32.6 (4)
C3—C4—C5—C23 −129.0 (4) C12—C13—C14—C15 −149.1 (3)
O1—C4—C5—C22 −63.7 (5) C26—C13—C14—C9 −70.9 (3)
C3—C4—C5—C22 114.7 (4) C17—C13—C14—C9 169.9 (2)
O1—C4—C5—C6 171.5 (4) C12—C13—C14—C9 53.4 (3)
C3—C4—C5—C6 −10.2 (4) C8—C9—C14—O3 −127.0 (3)
C2—C1—C6—C7 170.8 (3) C25—C9—C14—O3 −6.6 (4)
C10—C1—C6—C7 55.6 (3) C10—C9—C14—O3 117.5 (3)
C24—C1—C6—C7 −72.4 (3) C8—C9—C14—C15 −60.6 (4)
C2—C1—C6—C5 −55.4 (3) C25—C9—C14—C15 59.8 (4)
C10—C1—C6—C5 −170.6 (3) C10—C9—C14—C15 −176.1 (3)
C24—C1—C6—C5 61.3 (4) C8—C9—C14—C13 96.3 (3)
C4—C5—C6—C7 178.8 (3) C25—C9—C14—C13 −143.4 (3)
C23—C5—C6—C7 −64.0 (4) C10—C9—C14—C13 −19.2 (3)
C22—C5—C6—C7 57.7 (4) C14—O3—C15—C16 110.7 (3)
C4—C5—C6—C1 45.2 (4) C13—C14—C15—O3 100.1 (3)
C23—C5—C6—C1 162.4 (3) C9—C14—C15—O3 −102.2 (3)
supporting information
sup-7 Acta Cryst. (2004). E60, o1964–o1966
C1—C6—C7—C8 −56.3 (4) C13—C14—C15—C16 −5.4 (5)
C5—C6—C7—C8 168.5 (3) C9—C14—C15—C16 152.3 (3)
C6—C7—C8—O2 −119.2 (4) C17—O4—C16—O5 177.5 (3)
C6—C7—C8—C9 57.6 (4) C17—O4—C16—C15 −0.7 (5)
O2—C8—C9—C25 −116.2 (4) O3—C15—C16—O5 137.5 (4)
C7—C8—C9—C25 67.0 (4) C14—C15—C16—O5 −153.4 (3)
O2—C8—C9—C14 3.7 (5) O3—C15—C16—O4 −44.4 (4)
C7—C8—C9—C14 −173.0 (3) C14—C15—C16—O4 24.7 (5)
O2—C8—C9—C10 120.4 (4) C16—O4—C17—C18 −165.2 (3)
C7—C8—C9—C10 −56.4 (4) C16—O4—C17—C13 −40.1 (4)
C2—C1—C10—C11 58.0 (4) C14—C13—C17—O4 54.8 (3)
C6—C1—C10—C11 170.8 (3) C26—C13—C17—O4 −64.7 (3)
C24—C1—C10—C11 −58.9 (4) C12—C13—C17—O4 171.8 (3)
C2—C1—C10—C9 −171.4 (2) C14—C13—C17—C18 173.9 (3)
C6—C1—C10—C9 −58.6 (3) C26—C13—C17—C18 54.5 (3)
C24—C1—C10—C9 71.7 (3) C12—C13—C17—C18 −69.1 (3)
C8—C9—C10—C11 −164.8 (3) O4—C17—C18—C21 −147.3 (3)
C25—C9—C10—C11 75.9 (3) C13—C17—C18—C21 89.2 (4)
C14—C9—C10—C11 −43.8 (3) O4—C17—C18—C19 29.9 (5)
C8—C9—C10—C1 58.6 (3) C13—C17—C18—C19 −93.6 (4)
C25—C9—C10—C1 −60.7 (4) C21—C18—C19—C20 1.0 (5)
C14—C9—C10—C1 179.6 (2) C17—C18—C19—C20 −176.7 (3)
C1—C10—C11—C12 −150.9 (3) C18—C19—C20—O6 −1.5 (5)
C9—C10—C11—C12 75.1 (3) C21—O6—C20—C19 1.5 (5)
C10—C11—C12—C13 −38.9 (4) C19—C18—C21—O6 −0.1 (4)
C11—C12—C13—C14 −21.1 (4) C17—C18—C21—O6 177.6 (3)
C11—C12—C13—C26 101.0 (3) C20—O6—C21—C18 −0.8 (4)
C11—C12—C13—C17 −138.0 (3)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C11—H11B···O2i 0.97 2.35 3.288 (4) 162
C21—H21A···O5i 0.93 2.43 3.361 (5) 176
C23—H23A···O1 0.96 2.50 2.846 (6) 101
