organic papers
Acta Cryst.(2006). E62, o2195–o2197 doi:10.1107/S1600536806015807 Andolfiet al. C25H36O4
o2195
Acta Crystallographica Section EStructure Reports Online
ISSN 1600-5368
Ophiobolin A
Anna Andolfi,aAntonio
Evidente,aAntonello Santiniband Angela Tuzic*
aDipartimento di Scienze del Suolo, della Pianta
e dell’Ambiente, Universita` degli Studi di Napoli ‘Federico II’, Via Universita` 100, 80055 Portici, Italy,bDipartimento di Scienza degli Alimenti, Universita` degli Studi di Napoli ‘Federico II’, Via Universita` 100, 80055 Portici, Italy, and c
Dipartimento di Chimica, Universita` degli Studi di Napoli ‘Federico II’, Complesso Universitario di Monte S. Angelo, Via Cinthia, 80126 Napoli, Italy
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 173 K
Mean(C–C) = 0.007 A˚
Rfactor = 0.054
wRfactor = 0.114 Data-to-parameter ratio = 8.3
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 10 April 2006 Accepted 28 April 2006
#2006 International Union of Crystallography All rights reserved
The title compound, namely (20S,30S,3aR,50R,6aS,9R,9aS
,-10aR)-1,3a,4,40,50,6a,7,8,9,9a,10,10a-dodecahydro-9-hydroxy
-30,9,10a-trimethyl-50
-(2-methylpropen-1-yl)-7-oxospiro-[dicyclopenta[a,d]cyclooctene-3(2H),20(30H
)-furan]-6-carb-aldehyde, C25H36O4, displays phytotoxic behaviour that may
be correlated with some structural features of the molecule. The eight-membered ring of the terpenoid tricyclic skeleton is
cis- andtrans-joined with the fused five-membered rings. One intramolecular O—H O hydrogen bond and two inter-molecular C—H O hydrogen bonds are present.
Comment
Ophiobolin A was the first member of a group of polycyclic sesterterpenoids to be isolated and characterized (Ishibashi & Nakamura, 1958; Nozoe et al., 1965). Structural studies were reported on its methoxybromide and tetrahydro derivatives (Morisakiet al., 1968; Anastasiaet al., 1978). Ophiobolins have been extensively studied (Fujiwaraet al., 2000, Auet al., 2000). Recently, it has been shown that the phytotoxic behaviour of ophiobolin A may be correlated to some structural features of the molecule, such as the presence of the hydroxy group at C3, the aldehyde group at C7 and the stereochemistry at C6 (Evidente et al., 2006). Here, we report a low-temperature X-ray crystallographic analysis of ophiobolin A, (I), in order to contribute to a better understanding of the role of the stereochemistry of the carbotricyclic ring system in the affinity of the receptors.
5-position of the tetrahydrofuran ring (ring D). The absolute configuration of the molecule has been assigned in accordance with the methoxybromide derivative (Morisakiet al., 1968) as
S,R,S,R,R,S,S,Rat C2, C3, C6, C10, C11, C14, C15, C17, respectively. All bond lengths and angles (Table 1) are in normal ranges (Allenet al., 1987); only a slight contraction of the C10—C11—C12 angle may be noted, probably as a consequence of the puckering of ringCand its junction with ring B. Rings A andB are cis-joined (H2—C2—C6—H6 = 31.3), while rings B and C are trans-joined (C22—C11—
C10—H10 =179.7). BothAandCrings adopt an envelope
conformation, with atom C3 0.52 (6) A˚ out of the plane defined by atoms C2/C4/C5/C6 and atom C11 0.66 (5) A˚ out of the plane defined by atoms C10/C12/C13/C14.
The eight-membered ring B adopts a twist–boat confor-mation [atom C1 lies 0.39 (5) A˚ above and atom C11 lies 0.43 (5) A˚ below the plane defined by atoms C2/C6/C9/C10], which allows an intramolecular O—H O hydrogen bond. Two additional C—H O hydrogen bonds are present (Table 2), involving atoms C4 and C8. An envelope confor-mation is adopted by ring D, but, in contrast with the methoxybromide derivative, atom C17 atom is 0.50 (6) A˚ out of the plane through atoms O4/C14/C15/C16. In the isopropylidene side-chain, the mean plane of atoms C18/C19/ C24/C25 including the C18 C19 double bond is tilted with respect to the mean plane of ringDby 63.5 (3). Atransoid
conformation of the H atoms bound to C17 and C18 is adopted (H17—C17—C18—H18 = 149.8).
Experimental
Ophiobolin A was purified from the culture filtrate of Dreschlera gigantea (Biological Control of Weeds Collection at the Plant Pathology Department, University of Florida/IFAS, Gainesville, Florida, USA, No. LCLF-1), which was isolated during extensive field surveys in Florida from naturally infected large crabgrass (Digitaria sanguinalis). This fungus was grown as recently described by some of us (Evidenteet al., 2006). Its culture filtrates (2.7 l) were exhaustively extracted with EtOAc and the organic extract, showing a high phytotoxicity when assayed on detached leaves of Phalaris canar-iensis, was fractionated by column chromatography (CHCl3–
iPrOH,
94:6 v/v) followed by preparative thin-layer chromatography. The residue of the third fraction (149.0 mg) was crystallized three times from ethyl acetate–n-hexane (1:5 v/v) to give the main metabolite (43 mg) as a white crystalline powder. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a benzene solution.
Crystal data
C25H36O4
Mr= 400.54
Orthorhombic,P212121
a= 7.251 (4) A˚
b= 14.756 (9) A˚
c= 20.55 (2) A˚
V= 2199 (3) A˚3
Z= 4
Dx= 1.210 Mg m 3 MoKradiation
= 0.08 mm1
T= 173 (2) K Prism, colourless 0.200.200.07 mm
Data collection
Bruker Nonius KappaCCD area-detector diffractometer Thick–slice’and!scans Absorption correction: multi-scan
(SADABS; Bruker Nonius, 2002)
Tmin= 0.980,Tmax= 0.994
7226 measured reflections 2208 independent reflections 1356 reflections withI> 2(I)
Rint= 0.112
max= 25.0
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.054
wR(F2) = 0.114
S= 1.03 2208 reflections 267 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0367P)2 + 0.6026P]
whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001
max= 0.24 e A˚
3
min=0.25 e A˚
3
Table 1
Selected geometric parameters (A˚ ,).
O1—C3 1.434 (5) O2—C5 1.207 (6) O3—C21 1.202 (6) O4—C17 1.439 (6)
O4—C14 1.453 (5) C2—C6 1.556 (6) C10—C11 1.551 (6) C18—C19 1.315 (7)
C4—C3—C2 102.3 (4) O2—C5—C6 124.7 (5) C4—C5—C6 109.3 (4) C7—C6—C5 114.2 (4) C21—C7—C6 120.9 (4) C9—C10—C11 119.3 (4) C14—C10—C11 105.6 (4)
C12—C11—C10 98.5 (4) C1—C11—C10 115.8 (4) O4—C14—C15 105.2 (4) O4—C17—C16 103.6 (4) C18—C17—C16 114.5 (4) C19—C18—C17 128.0 (6) O3—C21—C7 125.4 (5)
O1—C3—C4—C5 90.6 (5) C3—C2—C6—C7 96.6 (5) C3—C2—C6—C5 29.8 (4) C14—C10—C11—C12 44.5 (4) C9—C10—C11—C1 66.0 (5)
C12—C13—C14—O4 122.9 (4) O4—C17—C18—C19 150.5 (5) C16—C17—C18—C19 94.3 (6) C8—C7—C21—O3 171.4 (5)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O1—H1 O3 0.84 2.01 2.794 (5) 154 C4—H4A O3i 0.99 2.47 3.352 (6) 148 C8—H8 O2ii
0.95 2.54 3.328 (6) 140
Symmetry codes: (i)xþ1 2;yþ
3
2;zþ1; (ii)x1;y;z.
organic papers
[image:2.610.47.296.72.211.2]o2196
Andolfiet al. C25H36O4 Acta Cryst.(2006). E62, o2195–o2197Figure 1
All H atoms were positioned geometrically, except for the hydroxy H atom, which was found in a difference Fourier map. They were constrained to standard bond lengths (Csp2—H = 0.95 A˚ , Csp3—H = 0.98, 0.99 and 1.00 A˚ for methyl, methylene and methyne groups, respectively, and O—H = 0.84 A˚ ) and allowed to ride on their parent atoms, with Uiso(H) = Ueq(C,O). In the absence of any significant
anomalous scattering, Friedel pairs were averaged prior to the final refinement and the absolute configuration was set by reference to the bromomethoxy derivative of ophiobolin A (Morisaki et al., 1968). The poor quality of the crystal may explain the rather high value of Rint.
Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ(Duisenberget al., 2000); data reduction:EVALCCD (Duisenberget al., 2003); program(s) used to solve structure:SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication:WinGX(Farrugia, 1999).
The authors thanks Professor Charudattan, Plant Pathology Department, University of Florida/IFAS, Gainsville, Florida, USA, and Maurizio Vurro, Istituto di Scienze delle Produzioni Alimentari, for the supply of the strain of Dreschlera gigantea and the fungal culture filtrate, respectively. Contribution DISSPA (111). Thanks are also due to the Centro Inter-dipartimentale di Metodologie Chimico Fisiche of the University of Naples ‘Federico II’ and to the Centro
Regio-nale di Competenza, Regione Campania, NTAP, for X-ray equipment.
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.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999).J. Appl. Cryst.32, 115–119.
Anastasia, M., Fiecchi, A., Galli Kienle, M., Scala, A., Bolognesi, M. & Rossi, G. (1978).Symp. Pap. 11th IUPAC Int. Symp. Chem. Nat. Prod.2, 108–111. Au, T. K., Chick, W. S. H. & Leung, P. C. (2000).Life Sci.67, 733–742. Bruker Nonius (2002).SADABS. Bruker Nonius, Delft, The Netherlands. Duisenberg, A. J. M., Hooft, R. W. W. & Schreurs, A. M. M. (2000).J. Appl.
Cryst.33, 893–898.
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003).
J. Appl. Cryst.36, 220–229.
Evidente, A., Andolfi, A., Cimmino, A., Vurro, M., Fracchiolla, M. & Charudattan, R. (2006).J. Agric. Food. Chem.54, 1779–1783.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565. Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838. Flack, H. D. (1983).Acta Cryst.A39, 876–881.
Fujiwara, H., Matsunaga, K., Kumagai, H., Ishizuka, M. & Ohizumi, Y. (2000).
Pharm. Pharmacol. Commun.6, 427–431.
Ishibashi, K. & Nakamura, R. (1958).J. Agric. Chem. Soc. Jpn, 32, 739– 744.
Morisaki, M., Nozoe, S. & Iitaka, Y. (1968).Acta Cryst.B24, 1293–1303. Nonius (1999).COLLECT. Nonius BV, Delft, The Netherlands.
Nozoe, S., Morisaki, M., Tsuda, K., Iitaka, Y., Takahashi, N., Tamura, S., Ishibashi, K. & Shirasaka, M. (1965).J. Am. Chem. Soc.87, 4968–70. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
Go¨ttingen, Germany.
organic papers
supporting information
sup-1
Acta Cryst. (2006). E62, o2195–o2197
supporting information
Acta Cryst. (2006). E62, o2195–o2197 [https://doi.org/10.1107/S1600536806015807]
Ophiobolin A
Anna Andolfi, Antonio Evidente, Antonello Santini and Angela Tuzi
(2′S,3′S,3aR,5′R,6aS,9R,9aS,10aR)-1,3a,4,4′,5′,6a,7,8,9,9a,10,10a- dodecahydro-9-hydroxy-3′,9,10a
-trimethyl-5′-(2-methylpropen-1-yl)-7- oxospiro[dicyclopenta[a,d]cyclooctene-3(2H),2′(3′H
)-furan]-6-carbaldehyde
Crystal data
C25H36O4 Mr = 400.54
Orthorhombic, P212121 Hall symbol: P 2ac 2ab
a = 7.251 (4) Å
b = 14.756 (9) Å
c = 20.55 (2) Å
V = 2199 (3) Å3 Z = 4
F(000) = 872
Dx = 1.210 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 192 reflections
θ = 4.1–24.2°
µ = 0.08 mm−1 T = 173 K Prism, colourless 0.20 × 0.20 × 0.07 mm
Data collection
Bruker Nonius KappaCCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
Detector resolution: 9 pixels mm-1 Thick–slice φ and ω scans Absorption correction: multi-scan
(SADABS; Bruker Nonius, 2002)
Tmin = 0.980, Tmax = 0.994
7226 measured reflections 2208 independent reflections 1356 reflections with I > 2σ(I)
Rint = 0.112
θmax = 25.0°, θmin = 3°
h = −8→7
k = −17→16
l = −24→20
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.054 wR(F2) = 0.114 S = 1.04 2208 reflections 267 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) + (0.0367P)2 + 0.6026P] where P = (Fo2 + 2Fc2)/3
supporting information
sup-2
Acta Cryst. (2006). E62, o2195–o2197
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 0.9599 (4) 0.5785 (2) 0.55823 (15) 0.0298 (9)
H1 0.9345 0.6298 0.5430 0.030*
O2 1.2591 (5) 0.6516 (2) 0.38921 (19) 0.0384 (10)
O3 0.9319 (5) 0.7256 (2) 0.47325 (18) 0.0359 (9)
O4 0.2862 (4) 0.4017 (2) 0.32500 (14) 0.0254 (8)
C1 0.7966 (6) 0.4362 (3) 0.4762 (2) 0.0209 (11)
H1A 0.7113 0.4865 0.4866 0.021*
H1B 0.8068 0.3982 0.5158 0.021*
C2 0.9863 (6) 0.4771 (3) 0.4628 (2) 0.0206 (12)
H2 1.0666 0.4256 0.4488 0.021*
C3 1.0823 (6) 0.5195 (3) 0.5234 (2) 0.0224 (12)
C4 1.2423 (6) 0.5728 (3) 0.4925 (2) 0.0275 (13)
H4A 1.2709 0.6273 0.5188 0.027*
H4B 1.3543 0.5346 0.4900 0.027*
C5 1.1801 (7) 0.5999 (3) 0.4252 (3) 0.0271 (12)
C6 1.0028 (6) 0.5502 (3) 0.4086 (2) 0.0234 (12)
H6 1.0236 0.5177 0.3665 0.023*
C7 0.8372 (7) 0.6116 (3) 0.3993 (2) 0.0233 (12)
C8 0.6930 (7) 0.5878 (3) 0.3629 (2) 0.0252 (12)
H8 0.5968 0.6311 0.3589 0.025*
C9 0.6670 (7) 0.4999 (3) 0.3277 (2) 0.0255 (12)
H9A 0.7875 0.4774 0.3119 0.025*
H9B 0.5856 0.5091 0.2896 0.025*
C10 0.5805 (6) 0.4298 (3) 0.3739 (2) 0.0163 (11)
H10 0.4943 0.4655 0.4019 0.016*
C11 0.7058 (6) 0.3780 (3) 0.4225 (2) 0.0202 (11)
C12 0.5579 (7) 0.3157 (3) 0.4529 (2) 0.0244 (12)
H12A 0.6161 0.2613 0.4722 0.024*
H12B 0.4895 0.3482 0.4874 0.024*
C13 0.4280 (7) 0.2888 (3) 0.3977 (2) 0.0254 (12)
H13A 0.2983 0.2909 0.4127 0.025*
H13B 0.4557 0.2265 0.3827 0.025*
C14 0.4586 (6) 0.3572 (3) 0.3417 (2) 0.0247 (12)
C15 0.5354 (7) 0.3191 (3) 0.2756 (2) 0.0277 (13)
supporting information
sup-3
Acta Cryst. (2006). E62, o2195–o2197
C16 0.4164 (7) 0.3667 (4) 0.2242 (2) 0.0307 (13)
H16A 0.4723 0.4250 0.2108 0.031*
H16B 0.4002 0.3280 0.1853 0.031*
C17 0.2326 (7) 0.3818 (3) 0.2591 (2) 0.0285 (13)
H17 0.1573 0.3251 0.2579 0.029*
C18 0.1223 (6) 0.4595 (4) 0.2337 (2) 0.0318 (14)
H18 0.1508 0.5172 0.2514 0.032*
C19 −0.0096 (7) 0.4577 (4) 0.1898 (2) 0.0363 (14)
C20 1.1435 (7) 0.4498 (4) 0.5724 (2) 0.0334 (14)
H20A 1.2119 0.4798 0.6075 0.033*
H20B 1.2232 0.4052 0.5511 0.033*
H20C 1.0351 0.4192 0.5906 0.033*
C21 0.8247 (7) 0.6984 (4) 0.4332 (3) 0.0312 (13)
H21 0.7233 0.7364 0.4227 0.031*
C22 0.8522 (6) 0.3181 (3) 0.3887 (2) 0.0226 (12)
H22A 0.9302 0.3560 0.3608 0.023*
H22B 0.7906 0.2720 0.3622 0.023*
H22C 0.9288 0.2885 0.4218 0.023*
C23 0.5289 (8) 0.2167 (4) 0.2665 (3) 0.0403 (15)
H23A 0.4008 0.1958 0.2695 0.040*
H23B 0.6027 0.1873 0.3004 0.040*
H23C 0.5788 0.2010 0.2236 0.040*
C24 −0.1017 (8) 0.5426 (5) 0.1668 (3) 0.0556 (19)
H24A −0.0512 0.5947 0.1904 0.056*
H24B −0.2347 0.5384 0.1749 0.056*
H24C −0.0797 0.5503 0.1201 0.056*
C25 −0.0768 (8) 0.3725 (5) 0.1568 (3) 0.0542 (19)
H25A −0.0414 0.3737 0.1108 0.054*
H25B −0.2114 0.3689 0.1603 0.054*
H25C −0.0213 0.3195 0.1779 0.054*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O1 0.032 (2) 0.024 (2) 0.034 (2) 0.0062 (16) 0.0032 (17) −0.0072 (17)
O2 0.029 (2) 0.041 (2) 0.045 (2) −0.0038 (18) 0.0115 (19) 0.009 (2)
O3 0.041 (2) 0.023 (2) 0.044 (2) 0.0047 (18) −0.006 (2) −0.0072 (19)
O4 0.0224 (18) 0.038 (2) 0.0154 (18) 0.0064 (16) −0.0032 (15) −0.0013 (16)
C1 0.020 (3) 0.021 (3) 0.022 (3) 0.004 (2) −0.002 (2) 0.004 (2)
C2 0.019 (3) 0.023 (3) 0.020 (3) 0.003 (2) 0.000 (2) −0.002 (2)
C3 0.019 (3) 0.023 (3) 0.025 (3) −0.001 (2) 0.001 (2) −0.003 (2)
C4 0.018 (3) 0.029 (3) 0.035 (3) −0.005 (2) −0.002 (2) −0.009 (2)
C5 0.017 (3) 0.027 (3) 0.037 (3) 0.005 (2) 0.006 (2) −0.001 (3)
C6 0.026 (3) 0.024 (3) 0.020 (3) 0.004 (2) 0.006 (2) −0.002 (2)
C7 0.026 (3) 0.019 (3) 0.024 (3) 0.001 (2) 0.003 (2) 0.000 (2)
C8 0.027 (3) 0.019 (3) 0.029 (3) 0.001 (2) 0.007 (2) 0.009 (2)
C9 0.028 (3) 0.032 (3) 0.016 (3) −0.003 (2) −0.003 (2) 0.007 (2)
supporting information
sup-4
Acta Cryst. (2006). E62, o2195–o2197
C11 0.021 (3) 0.022 (3) 0.018 (3) −0.002 (2) −0.002 (2) 0.002 (2)
C12 0.027 (3) 0.027 (3) 0.019 (3) −0.007 (2) −0.004 (2) 0.002 (2)
C13 0.025 (3) 0.026 (3) 0.025 (3) −0.004 (2) 0.004 (2) 0.000 (2)
C14 0.018 (3) 0.028 (3) 0.028 (3) 0.008 (2) 0.000 (2) −0.003 (2)
C15 0.022 (3) 0.033 (3) 0.028 (3) 0.003 (2) 0.002 (2) −0.002 (3)
C16 0.023 (3) 0.048 (4) 0.021 (3) 0.001 (3) −0.001 (2) −0.002 (3)
C17 0.024 (3) 0.042 (3) 0.020 (3) 0.000 (3) −0.004 (2) −0.007 (3)
C18 0.026 (3) 0.042 (4) 0.027 (3) 0.003 (3) 0.004 (3) 0.006 (3)
C19 0.020 (3) 0.069 (4) 0.020 (3) 0.011 (3) 0.005 (2) 0.010 (3)
C20 0.037 (3) 0.035 (4) 0.028 (3) −0.002 (3) −0.008 (3) −0.005 (3)
C21 0.034 (3) 0.023 (3) 0.036 (3) 0.008 (3) 0.005 (3) 0.005 (3)
C22 0.023 (3) 0.022 (3) 0.023 (3) 0.000 (2) −0.007 (2) −0.003 (2)
C23 0.036 (3) 0.050 (4) 0.035 (4) −0.001 (3) −0.007 (3) −0.009 (3)
C24 0.040 (4) 0.088 (5) 0.039 (4) 0.019 (4) 0.004 (3) 0.026 (4)
C25 0.032 (3) 0.096 (6) 0.034 (4) 0.007 (3) −0.007 (3) −0.004 (4)
Geometric parameters (Å, º)
O1—C3 1.434 (5) C12—H12A 0.9900
O1—H1 0.8400 C12—H12B 0.9900
O2—C5 1.207 (6) C13—C14 1.546 (7)
O3—C21 1.202 (6) C13—H13A 0.9900
O4—C17 1.439 (6) C13—H13B 0.9900
O4—C14 1.453 (5) C14—C15 1.573 (7)
C1—C2 1.527 (6) C15—C23 1.524 (7)
C1—C11 1.546 (6) C15—C16 1.534 (7)
C1—H1A 0.9900 C15—H15 1.0000
C1—H1B 0.9900 C16—C17 1.530 (7)
C2—C6 1.556 (6) C16—H16A 0.9900
C2—C3 1.557 (6) C16—H16B 0.9900
C2—H2 1.0000 C17—C18 1.491 (7)
C3—C20 1.506 (7) C17—H17 1.0000
C3—C4 1.539 (7) C18—C19 1.315 (7)
C4—C5 1.509 (7) C18—H18 0.9500
C4—H4A 0.9900 C19—C24 1.496 (8)
C4—H4B 0.9900 C19—C25 1.510 (8)
C5—C6 1.519 (7) C20—H20A 0.9800
C6—C7 1.515 (6) C20—H20B 0.9800
C6—H6 1.0000 C20—H20C 0.9800
C7—C8 1.332 (7) C21—H21 0.9500
C7—C21 1.460 (7) C22—H22A 0.9800
C8—C9 1.497 (7) C22—H22B 0.9800
C8—H8 0.9500 C22—H22C 0.9800
C9—C10 1.537 (6) C23—H23A 0.9800
C9—H9A 0.9900 C23—H23B 0.9800
C9—H9B 0.9900 C23—H23C 0.9800
C10—C14 1.538 (6) C24—H24A 0.9800
supporting information
sup-5
Acta Cryst. (2006). E62, o2195–o2197
C10—H10 1.0000 C24—H24C 0.9800
C11—C12 1.544 (6) C25—H25A 0.9800
C11—C22 1.546 (6) C25—H25B 0.9800
C12—C13 1.527 (6) C25—H25C 0.9800
C3—O1—H1 119.8 C14—C13—H13A 110.3
C17—O4—C14 111.3 (3) C12—C13—H13B 110.3
C2—C1—C11 118.3 (4) C14—C13—H13B 110.3
C2—C1—H1A 107.7 H13A—C13—H13B 108.5
C11—C1—H1A 107.7 O4—C14—C10 106.3 (4)
C2—C1—H1B 107.7 O4—C14—C13 110.3 (4)
C11—C1—H1B 107.7 C10—C14—C13 102.5 (4)
H1A—C1—H1B 107.1 O4—C14—C15 105.2 (4)
C1—C2—C6 118.2 (4) C10—C14—C15 114.7 (4)
C1—C2—C3 114.7 (4) C13—C14—C15 117.4 (4)
C6—C2—C3 105.0 (4) C23—C15—C16 110.6 (4)
C1—C2—H2 106.0 C23—C15—C14 116.8 (4)
C6—C2—H2 106.0 C16—C15—C14 103.4 (4)
C3—C2—H2 106.0 C23—C15—H15 108.6
O1—C3—C20 105.2 (4) C16—C15—H15 108.6
O1—C3—C4 111.2 (4) C14—C15—H15 108.6
C20—C3—C4 113.8 (4) C17—C16—C15 103.5 (4)
O1—C3—C2 111.5 (4) C17—C16—H16A 111.1
C20—C3—C2 113.1 (4) C15—C16—H16A 111.1
C4—C3—C2 102.3 (4) C17—C16—H16B 111.1
C5—C4—C3 106.7 (4) C15—C16—H16B 111.1
C5—C4—H4A 110.4 H16A—C16—H16B 109.0
C3—C4—H4A 110.4 O4—C17—C18 108.5 (4)
C5—C4—H4B 110.4 O4—C17—C16 103.6 (4)
C3—C4—H4B 110.4 C18—C17—C16 114.5 (4)
H4A—C4—H4B 108.6 O4—C17—H17 110.0
O2—C5—C4 125.9 (5) C18—C17—H17 110.0
O2—C5—C6 124.7 (5) C16—C17—H17 110.0
C4—C5—C6 109.3 (4) C19—C18—C17 128.0 (6)
C7—C6—C5 114.2 (4) C19—C18—H18 116.0
C7—C6—C2 116.3 (4) C17—C18—H18 116.0
C5—C6—C2 103.8 (4) C18—C19—C24 121.7 (6)
C7—C6—H6 107.3 C18—C19—C25 124.0 (6)
C5—C6—H6 107.3 C24—C19—C25 114.3 (5)
C2—C6—H6 107.3 C3—C20—H20A 109.5
C8—C7—C21 116.7 (5) C3—C20—H20B 109.5
C8—C7—C6 122.3 (4) H20A—C20—H20B 109.5
C21—C7—C6 120.9 (4) C3—C20—H20C 109.5
C7—C8—C9 126.7 (4) H20A—C20—H20C 109.5
C7—C8—H8 116.6 H20B—C20—H20C 109.5
C9—C8—H8 116.6 O3—C21—C7 125.4 (5)
C8—C9—C10 109.6 (4) O3—C21—H21 117.3
supporting information
sup-6
Acta Cryst. (2006). E62, o2195–o2197
C10—C9—H9A 109.7 C11—C22—H22A 109.5
C8—C9—H9B 109.7 C11—C22—H22B 109.5
C10—C9—H9B 109.7 H22A—C22—H22B 109.5
H9A—C9—H9B 108.2 C11—C22—H22C 109.5
C9—C10—C14 115.9 (4) H22A—C22—H22C 109.5
C9—C10—C11 119.3 (4) H22B—C22—H22C 109.5
C14—C10—C11 105.6 (4) C15—C23—H23A 109.5
C9—C10—H10 104.8 C15—C23—H23B 109.5
C14—C10—H10 104.8 H23A—C23—H23B 109.5
C11—C10—H10 104.8 C15—C23—H23C 109.5
C12—C11—C22 108.6 (4) H23A—C23—H23C 109.5
C12—C11—C1 109.7 (4) H23B—C23—H23C 109.5
C22—C11—C1 110.2 (4) C19—C24—H24A 109.5
C12—C11—C10 98.5 (4) C19—C24—H24B 109.5
C22—C11—C10 113.3 (4) H24A—C24—H24B 109.5
C1—C11—C10 115.8 (4) C19—C24—H24C 109.5
C13—C12—C11 106.4 (4) H24A—C24—H24C 109.5
C13—C12—H12A 110.5 H24B—C24—H24C 109.5
C11—C12—H12A 110.5 C19—C25—H25A 109.5
C13—C12—H12B 110.5 C19—C25—H25B 109.5
C11—C12—H12B 110.5 H25A—C25—H25B 109.5
H12A—C12—H12B 108.6 C19—C25—H25C 109.5
C12—C13—C14 107.1 (4) H25A—C25—H25C 109.5
C12—C13—H13A 110.3 H25B—C25—H25C 109.5
C11—C1—C2—C6 65.8 (6) C9—C10—C11—C1 66.0 (5)
C11—C1—C2—C3 −169.4 (4) C14—C10—C11—C1 −161.3 (4)
C1—C2—C3—O1 −48.5 (5) C22—C11—C12—C13 −80.6 (5)
C6—C2—C3—O1 82.9 (4) C1—C11—C12—C13 158.9 (4)
C1—C2—C3—C20 69.8 (5) C10—C11—C12—C13 37.5 (5)
C6—C2—C3—C20 −158.8 (4) C11—C12—C13—C14 −17.9 (5)
C1—C2—C3—C4 −167.5 (4) C17—O4—C14—C10 132.1 (4)
C6—C2—C3—C4 −36.0 (4) C17—O4—C14—C13 −117.4 (4)
O1—C3—C4—C5 −90.6 (5) C17—O4—C14—C15 10.1 (5)
C20—C3—C4—C5 150.9 (4) C9—C10—C14—O4 −75.1 (5)
C2—C3—C4—C5 28.6 (5) C11—C10—C14—O4 150.3 (4)
C3—C4—C5—O2 170.4 (5) C9—C10—C14—C13 169.0 (4)
C3—C4—C5—C6 −10.7 (5) C11—C10—C14—C13 34.5 (4)
O2—C5—C6—C7 −65.3 (6) C9—C10—C14—C15 40.6 (5)
C4—C5—C6—C7 115.8 (5) C11—C10—C14—C15 −93.9 (4)
O2—C5—C6—C2 167.0 (5) C12—C13—C14—O4 −122.9 (4)
C4—C5—C6—C2 −11.9 (5) C12—C13—C14—C10 −9.9 (5)
C1—C2—C6—C7 32.8 (6) C12—C13—C14—C15 116.7 (4)
C3—C2—C6—C7 −96.6 (5) O4—C14—C15—C23 −108.6 (5)
C1—C2—C6—C5 159.2 (4) C10—C14—C15—C23 135.0 (5)
C3—C2—C6—C5 29.8 (4) C13—C14—C15—C23 14.5 (6)
C5—C6—C7—C8 154.9 (5) O4—C14—C15—C16 13.1 (5)
supporting information
sup-7
Acta Cryst. (2006). E62, o2195–o2197
C5—C6—C7—C21 −28.4 (7) C13—C14—C15—C16 136.2 (4)
C2—C6—C7—C21 92.6 (5) C23—C15—C16—C17 95.9 (5)
C21—C7—C8—C9 −175.2 (4) C14—C15—C16—C17 −29.9 (5)
C6—C7—C8—C9 1.6 (8) C14—O4—C17—C18 −151.4 (4)
C7—C8—C9—C10 86.2 (6) C14—O4—C17—C16 −29.3 (5)
C8—C9—C10—C14 150.4 (4) C15—C16—C17—O4 36.3 (5)
C8—C9—C10—C11 −81.5 (5) C15—C16—C17—C18 154.3 (4)
C2—C1—C11—C12 159.0 (4) O4—C17—C18—C19 −150.5 (5)
C2—C1—C11—C22 39.5 (5) C16—C17—C18—C19 94.3 (6)
C2—C1—C11—C10 −90.7 (5) C17—C18—C19—C24 −176.9 (5)
C9—C10—C11—C12 −177.2 (4) C17—C18—C19—C25 1.0 (9)
C14—C10—C11—C12 −44.5 (4) C8—C7—C21—O3 171.4 (5)
C9—C10—C11—C22 −62.7 (5) C6—C7—C21—O3 −5.4 (8)
C14—C10—C11—C22 70.0 (5)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O1—H1···O3 0.84 2.01 2.794 (5) 154
C4—H4A···O3i 0.99 2.47 3.352 (6) 148
C8—H8···O2ii 0.95 2.54 3.328 (6) 140
