Melampodinone

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organic papers

o874

Fronczek and Fischer C₂₁H₂₂O₁₀ DOI: 10.1107/S1600536802011844 Acta Cryst.(2002). E58, o874±o876 Acta Crystallographica Section E

Structure Reports

Online ISSN 1600-5368

Melampodinone

Frank R. Fronczeka_{* and}

Nikolaus H. Fischerb

a_{Department of Chemistry, Louisiana State}

University, Baton Rouge, LA 70803-1804, USA, andb_{Department of Pharmacognosy, Research} Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 120 K

Mean(C±C) = 0.003 AÊ

Rfactor = 0.042

wRfactor = 0.090

Data-to-parameter ratio = 11.7

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

The title compound, methyl {1aS-[1aR*,2aR*,3aR*,4E,5aS *,-8aR*,9R*(2S*,3S*),9aR *]}-9-{[(2,3-dimethyloxiranyl)carbon- yl]oxy}-2a,3a,5a,7,8,8a,9,9a-octahydro-4-methyl-8-methylene-2,7-dioxobisoxireno[4,5:7,8]cyclodeca[1,2-b]furan-1a(2H )-car-boxylate, C21H22O10, is an oxidation product of melampodin

A. It hasZ0_{= 2, and the conformations of the ten-membered}

rings in the two molecules are quite similar, with a mean difference of 2.4_{between endocyclic torsion angles.}

Comment

The structure of melampodin A, which differs from the title compound, (I), only by having acis-double bond at C1 C10 and an OH group at C9 instead of the ketone at C1 and epoxide at C9ÐC10, has been reported, based on X-ray (Watkins et al., 1973) and neutron (Neidle & Rogers, 1972) data. CrO3 oxidation of melampodin A fromMelampodium

leucanthumhas led to the title keto compound (Fischeret al., 1975). The formation of a rearranged ketone at C1 rather than C9 appears to result from a relief of strain in the ten-membered ring, and the structure of (I) was studied in order to determine the ten-ring conformation.

There are two independent molecules in the asymmetric unit of (I), and their conformations are described by the endocyclic torsion angles in Table 1. The ten-membered rings of the two molecules have very similar conformations, with a mean difference of 2.4_{between endocyclic torsion angles, the}

maximum difference being only 4.0 (4) _{for the torsion angle}

about C1ÐC10. This conformation differs from the typical melampolide conformation (Fronczek et al., 1986, and refer-ences therein) mainly in the portion of the ring near the C1Ð C2 bond. Typical melampolides tend to have endocyclic torsion angles near zero,ÿ100_{, and 70}_{about C1 C10, C1Ð}

C2, and C2ÐC3, respectively.

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The conformations of the epoxyangelate substituents at C8 in the two independent molecules of melampodinone differ by somewhat more than those of the ten-membered rings. The torsion angles about C8ÐO8 differ by 11.8 (3)_{, and those}

about C17ÐC18 by 21.7 (4)_.

Cell dimensions at 293 K area= 7.777 (2),b= 11.681 (4), andc= 23.812 (4) AÊ, and= 97.67 (2)_{; thus,}_Z0_{= 2 is not a}

result of a phase change on cooling.

Experimental

The preparation of the title compound by epoxidation of melampodin A using CrO3 in glacial acetic acid has been previously described

(Fischeret al., 1975). Crystals were grown from methanol.

Crystal data

C21H22O10

Mr= 434.39

Monoclinic,P21

a= 7.646 (2) AÊ b= 11.633 (2) AÊ c= 23.709 (4) AÊ

= 97.385 (6)

V= 2091.3 (7) AÊ3

Z= 4

Dx= 1.380 Mg mÿ3

MoKradiation Cell parameters from 6013

re¯ections

= 2.5±30.5

= 0.11 mmÿ1

T= 120 K Fragment, colorless 0.470.350.25 mm

Data collection

KappaCCD diffractometer (with Oxford Cryosystems Cryostream cooler)

!scans withoffsets 23 672 measured re¯ections 6629 independent re¯ections

5688 re¯ections withI> 2(I) Rint= 0.025

max= 30.5

h=ÿ10!10 k=ÿ16!16 l=ÿ33!33

Re®nement

Re®nement onF2

R[F2_{> 2}₍_F2_{)] = 0.042}

wR(F2_{) = 0.090}

S= 1.05 6629 re¯ections 568 parameters

H-atom parameters constrained

w= 1/[2₍_F

o2) + (0.0326P)2

+ 0.6091P]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.001 max= 0.26 e AÊÿ3 min=ÿ0.20 e AÊÿ3

Extinction correction:SHELXL97 Extinction coef®cient: 0.0074 (11)

Table 1

Selected geometric parameters (AÊ,_).

O3ÐC1 1.201 (3)

O4ÐC10 1.442 (2)

O4ÐC9 1.442 (3)

O7ÐC2 1.434 (3)

O7ÐC3 1.435 (3)

O10ÐC18 1.436 (3) O10ÐC19 1.449 (3)

C4ÐC5 1.338 (3)

O30_ÐC10 _{1.199 (3)}

O40_ÐC100 _{1.435 (3)}

O40_ÐC90 _{1.437 (3)}

O70_ÐC20 _{1.432 (3)}

O70_ÐC30 _{1.435 (4)}

O100_ÐC180 _{1.440 (3)}

O100_ÐC190 _{1.445 (3)}

C40_ÐC50 _{1.338 (3)}

C10ÐC1ÐC2ÐC3 62.6 (3) C1ÐC2ÐC3ÐC4 ÿ3.4 (3) C2ÐC3ÐC4ÐC5 ÿ86.3 (3) C3ÐC4ÐC5ÐC6 162.63 (19) C4ÐC5ÐC6ÐC7 ÿ123.9 (2) C5ÐC6ÐC7ÐC8 84.9 (2) C17ÐO8ÐC8ÐC7 137.91 (17) C6ÐC7ÐC8ÐC9 ÿ45.4 (2) C7ÐC8ÐC9ÐC10 ÿ67.1 (3) C8ÐC9ÐC10ÐC1 155.57 (19) C2ÐC1ÐC10ÐC9 ÿ110.6 (2) O8ÐC17ÐC18ÐC20 ÿ42.3 (3)

C100_ÐC10_ÐC20_ÐC30 _{65.8 (3)}

C10_ÐC20_ÐC30_ÐC40 _{ÿ4.4 (4)}

C20_ÐC30_ÐC40_ÐC50 _{ÿ87.9 (3)}

C30_ÐC40_ÐC50_ÐC60 _{160.5 (2)}

C40_ÐC50_ÐC60_ÐC70 _{ÿ121.0 (3)}

C50_ÐC60_ÐC70_ÐC80 _{86.3 (2)}

C170_ÐO80_ÐC80_ÐC70 _{126.12 (19)}

C60_ÐC70_ÐC80_ÐC90 _{ÿ48.3 (2)}

C70_ÐC80_ÐC90_ÐC100 _{ÿ71.1 (3)}

C80_ÐC90_ÐC100_ÐC10 _{154.2 (2)}

C20_ÐC10_ÐC100_ÐC90 _{ÿ106.6 (3)}

O80_ÐC170_ÐC180_ÐC200 _{ÿ20.6 (3)}

Friedel pairs were averaged before re®nement. H atoms were placed in calculated positions, with CÐH distances in the range 0.95± 1.00 AÊ andUiso = 1.2Ueqof the attached atom (1.5Ueqfor methyl

groups), and thereafter treated as riding. A torsional parameter was re®ned for each methyl group. The absolute con®guration could not be determined, and was assigned based on the known con®guration of the starting material (Neidle & Rogers, 1972).

Data collection: COLLECT (Nonius, 2000); cell re®nement:

DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure:SIR97 (Altomareet al., 1999); 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:SHELXL97.

The purchase of the diffractometer was made possible by grant No. LEQSF(1999±2000)-ESH-TR-13, administered by the Louisiana Board of Regents.

References

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.

Farrugia, L. J. (1997).J. Appl. Cryst.30, 565. Figure 1

The atom-numbering scheme for the unprimed molecule, with ellipsoids at the 50% probability level.

Figure 2

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organic papers

o876

Fronczek and Fischer C₂₁H₂₂O₁₀ Acta Cryst.(2002). E58, o874±o876

Fischer, N. H., Wiley, R. A. Jr, Lin, H.-N., Karimian, K. & Politz, S. M. (1975). Phytochemistry,14, 2241±2245.

Fronczek, F. R., Vargas, D. & Fischer, N. H. (1986).Acta Cryst.C42, 1061±1063. Neidle, S. & Rogers, D. (1972).J. Chem. Soc. Chem. Commun.pp. 140±141. Nonius (2000).COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307±326. New York: Academic Press.

Sheldrick, G. M. (1997).SHELXL97. University of GoÈttingen, Germany. Watkins, S. F., Fischer, N. H. & Bernal, I. (1973).Proc. Natl Acad. Sci. USA,70,

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supporting information

Acta Cryst. (2002). E58, o874–o876 [https://doi.org/10.1107/S1600536802011844]

Melampodinone

Frank R. Fronczek and Nikolaus H. Fischer

(I)

Crystal data

C21H22O10

Mr = 434.39

Monoclinic, P21 Hall symbol: P 2yb

a = 7.646 (2) Å

b = 11.633 (2) Å

c = 23.709 (4) Å

β = 97.385 (6)°

V = 2091.3 (7) Å3

Z = 4

F(000) = 912

Dx = 1.380 Mg m−3

Melting point: 492-495K K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 6013 reflections

θ = 2.5–30.5°

µ = 0.11 mm−1

T = 120 K

Fragment, colorless 0.47 × 0.35 × 0.25 mm

Data collection

KappaCCD (with Oxford Cryosystems Cryostream cooler)

diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω scans with κ offsets 23672 measured reflections

6629 independent reflections 5688 reflections with I > 2σ(I)

Rint = 0.025

θmax = 30.5°, θmin = 2.6°

h = −10→10

k = −16→16

l = −33→33

Refinement

Refinement on F2 Least-squares matrix: full

R[F2_{> 2}_σ₍_F2_{)] = 0.042}

wR(F2_{) = 0.090}

S = 1.05 6629 reflections 568 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) + (0.0326P)2 + 0.6091P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max = 0.001 Δρmax = 0.26 e Å−3 Δρmin = −0.20 e Å−3

Extinction correction: SHELXL97, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2_θ_)]-1/4 Extinction coefficient: 0.0074 (11)

Special details

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Acta Cryst. (2002). E58, o874–o876

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 0.28331 (18) 0.00036 (13) 0.56993 (6) 0.0204 (3) O2 0.4839 (2) −0.13872 (14) 0.58788 (7) 0.0301 (4) O3 −0.0298 (2) 0.51331 (16) 0.64556 (7) 0.0310 (4) O4 0.2757 (2) 0.42377 (13) 0.69863 (6) 0.0238 (3) O5 0.5202 (2) 0.38905 (14) 0.60432 (8) 0.0297 (4) O6 0.3654 (2) 0.55119 (13) 0.58477 (7) 0.0255 (3) O7 0.1026 (2) 0.41375 (14) 0.51292 (6) 0.0264 (3) O8 0.32393 (19) 0.14307 (13) 0.72733 (6) 0.0210 (3) O9 0.4951 (3) 0.23224 (19) 0.79823 (7) 0.0481 (5) O10 0.4073 (2) 0.06612 (18) 0.87590 (6) 0.0356 (4) C1 0.0588 (3) 0.46590 (19) 0.61429 (9) 0.0218 (4) C2 −0.0085 (3) 0.4581 (2) 0.55216 (9) 0.0244 (4)

H2 −0.0881 0.5223 0.5371 0.029*

C3 −0.0461 (3) 0.3451 (2) 0.52319 (9) 0.0252 (4)

H3 −0.1475 0.3436 0.4920 0.030*

C4 −0.0081 (3) 0.23570 (19) 0.55482 (9) 0.0212 (4) C5 0.1542 (3) 0.19118 (18) 0.55784 (8) 0.0189 (4)

H5 0.2275 0.2184 0.5313 0.023*

C6 0.2292 (3) 0.10277 (17) 0.59921 (8) 0.0178 (4)

H6 0.1422 0.0819 0.6256 0.021*

C7 0.4028 (2) 0.14662 (17) 0.63311 (8) 0.0169 (4)

H7 0.4636 0.1951 0.6067 0.020*

C8 0.3806 (3) 0.22003 (17) 0.68512 (8) 0.0186 (4)

H8 0.4956 0.2564 0.7002 0.022*

C9 0.2383 (3) 0.31119 (18) 0.67457 (8) 0.0184 (4)

H9 0.1176 0.2824 0.6791 0.022*

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H16C 0.5094 0.5436 0.5200 0.052* C17 0.3967 (3) 0.1562 (2) 0.78179 (9) 0.0247 (4) C18 0.3360 (3) 0.0594 (2) 0.81694 (8) 0.0265 (5) C19 0.4686 (4) −0.0255 (3) 0.84194 (10) 0.0384 (6) H19 0.4200 −0.1033 0.8489 0.046* C20 0.1442 (3) 0.0270 (2) 0.80486 (10) 0.0305 (5) H20A 0.1177 −0.0331 0.8314 0.046* H20B 0.1191 −0.0016 0.7658 0.046* H20C 0.0711 0.0947 0.8095 0.046* C21 0.6602 (4) −0.0239 (4) 0.83443 (13) 0.0579 (10) H21A 0.6960 0.0549 0.8269 0.087* H21B 0.6797 −0.0733 0.8023 0.087* H21C 0.7303 −0.0523 0.8692 0.087* O1′ 0.0386 (2) 0.32377 (15) 0.80503 (8) 0.0325 (4) O2′ −0.1587 (2) 0.27579 (18) 0.73059 (8) 0.0408 (5) O3′ 0.3925 (3) 0.74747 (19) 0.97808 (9) 0.0484 (5) O4′ 0.1170 (2) 0.78812 (14) 0.89640 (7) 0.0291 (4) O5′ −0.1968 (2) 0.6498 (2) 0.92501 (7) 0.0422 (5) O6′ −0.0378 (2) 0.67878 (16) 1.01044 (6) 0.0324 (4) O7′ 0.1772 (3) 0.48272 (17) 1.00935 (7) 0.0399 (4) O8′ 0.0889 (2) 0.66154 (13) 0.77327 (6) 0.0232 (3) O9′ −0.1085 (2) 0.79615 (16) 0.73917 (7) 0.0322 (4) O10′ 0.1378 (2) 0.88097 (14) 0.67055 (7) 0.0288 (4) C1′ 0.2801 (3) 0.6750 (2) 0.97469 (10) 0.0310 (5) C2′ 0.3103 (4) 0.5696 (3) 1.01063 (11) 0.0389 (6)

H2′ 0.3791 0.5827 1.0489 0.047*

C3′ 0.3360 (4) 0.4551 (3) 0.98589 (12) 0.0408 (6)

H3′ 0.4201 0.4028 1.0093 0.049*

C4′ 0.3201 (3) 0.4383 (2) 0.92300 (11) 0.0329 (5) C5′ 0.1609 (3) 0.4155 (2) 0.89486 (11) 0.0297 (5)

H5′ 0.0744 0.3871 0.9167 0.036*

C6′ 0.1056 (3) 0.42999 (19) 0.83278 (10) 0.0255 (4)

H6′ 0.2061 0.4603 0.8140 0.031*

C7′ −0.0517 (3) 0.51425 (19) 0.82377 (9) 0.0214 (4) H7′ −0.1223 0.5031 0.8560 0.026* C8′ −0.0007 (3) 0.64063 (19) 0.82299 (8) 0.0210 (4) H8′ −0.1080 0.6902 0.8217 0.025* C9′ 0.1359 (3) 0.67680 (19) 0.87163 (9) 0.0225 (4)

H9′ 0.2597 0.6586 0.8652 0.027*

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supporting information

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Acta Cryst. (2002). E58, o874–o876

H15E 0.5780 0.4003 0.9156 0.070* H15F 0.5301 0.5325 0.9030 0.070* C16′ −0.1851 (4) 0.6423 (3) 1.03954 (11) 0.0406 (6) H16D −0.2917 0.6842 1.0240 0.061* H16E −0.1581 0.6585 1.0803 0.061* H16F −0.2044 0.5596 1.0339 0.061* C17′ 0.0271 (3) 0.74616 (19) 0.73718 (9) 0.0221 (4) C18′ 0.1573 (3) 0.76786 (19) 0.69522 (9) 0.0228 (4) C19′ 0.0878 (3) 0.78337 (19) 0.63437 (9) 0.0240 (4) H19′ 0.1737 0.7639 0.6074 0.029* C20′ 0.3439 (3) 0.7284 (2) 0.71172 (10) 0.0294 (5) H20D 0.4147 0.7482 0.6815 0.044* H20E 0.3455 0.6449 0.7173 0.044* H20F 0.3932 0.7663 0.7471 0.044* C21′ −0.1019 (3) 0.7762 (2) 0.60909 (9) 0.0279 (5) H21D −0.1761 0.7670 0.6396 0.042* H21E −0.1184 0.7101 0.5833 0.042* H21F −0.1353 0.8468 0.5878 0.042*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

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C17 0.0272 (10) 0.0301 (12) 0.0164 (9) 0.0006 (9) 0.0015 (8) −0.0032 (8) C18 0.0345 (11) 0.0319 (12) 0.0127 (8) 0.0054 (10) 0.0012 (8) −0.0003 (8) C19 0.0492 (14) 0.0469 (16) 0.0189 (11) 0.0188 (13) 0.0038 (10) 0.0041 (11) C20 0.0394 (13) 0.0287 (12) 0.0232 (10) −0.0042 (10) 0.0030 (9) 0.0056 (9) C21 0.0482 (16) 0.093 (3) 0.0322 (14) 0.0318 (18) 0.0022 (12) 0.0055 (16) O1′ 0.0320 (8) 0.0233 (8) 0.0412 (10) −0.0031 (7) 0.0011 (7) −0.0070 (7) O2′ 0.0382 (10) 0.0407 (11) 0.0444 (11) −0.0114 (9) 0.0088 (8) −0.0192 (9) O3′ 0.0399 (11) 0.0505 (13) 0.0506 (12) −0.0194 (10) −0.0100 (9) −0.0005 (10) O4′ 0.0435 (9) 0.0199 (8) 0.0236 (8) −0.0050 (7) 0.0034 (7) 0.0006 (6) O5′ 0.0294 (8) 0.0682 (14) 0.0293 (9) −0.0098 (9) 0.0056 (7) −0.0127 (9) O6′ 0.0359 (9) 0.0419 (10) 0.0201 (7) −0.0041 (8) 0.0063 (6) 0.0004 (7) O7′ 0.0518 (11) 0.0369 (10) 0.0291 (9) −0.0025 (9) −0.0024 (8) 0.0091 (8) O8′ 0.0280 (7) 0.0239 (8) 0.0183 (7) 0.0038 (6) 0.0052 (6) 0.0039 (6) O9′ 0.0347 (9) 0.0345 (10) 0.0285 (9) 0.0121 (8) 0.0085 (7) 0.0093 (7) O10′ 0.0434 (9) 0.0188 (8) 0.0249 (8) −0.0024 (7) 0.0063 (7) 0.0020 (6) C1′ 0.0302 (11) 0.0385 (14) 0.0229 (10) −0.0043 (11) −0.0024 (9) −0.0040 (10) C2′ 0.0391 (14) 0.0446 (16) 0.0287 (12) 0.0003 (12) −0.0123 (10) 0.0031 (11) C3′ 0.0405 (14) 0.0392 (15) 0.0374 (14) 0.0076 (12) −0.0156 (11) 0.0075 (12) C4′ 0.0323 (12) 0.0275 (12) 0.0367 (13) 0.0052 (10) −0.0042 (10) 0.0026 (10) C5′ 0.0304 (11) 0.0219 (11) 0.0350 (12) 0.0009 (9) −0.0023 (9) 0.0070 (9) C6′ 0.0238 (10) 0.0216 (11) 0.0303 (11) −0.0014 (9) 0.0007 (9) −0.0010 (9) C7′ 0.0216 (9) 0.0240 (10) 0.0186 (9) −0.0011 (8) 0.0021 (7) 0.0013 (8) C8′ 0.0244 (10) 0.0232 (10) 0.0158 (9) 0.0018 (8) 0.0041 (7) 0.0020 (8) C9′ 0.0258 (10) 0.0209 (10) 0.0209 (9) −0.0010 (8) 0.0034 (8) 0.0025 (8) C10′ 0.0271 (10) 0.0246 (11) 0.0175 (9) −0.0050 (9) −0.0002 (8) 0.0017 (8) C11′ 0.0236 (10) 0.0316 (12) 0.0207 (10) −0.0058 (9) 0.0044 (8) −0.0037 (9) C12′ 0.0264 (10) 0.0319 (12) 0.0284 (11) −0.0057 (10) 0.0085 (9) −0.0046 (10) C13′ 0.0286 (11) 0.0478 (16) 0.0311 (12) −0.0028 (12) −0.0035 (9) −0.0068 (12) C14′ 0.0318 (11) 0.0290 (12) 0.0208 (10) −0.0026 (10) 0.0055 (9) −0.0010 (9) C15′ 0.0288 (12) 0.0494 (18) 0.0598 (18) 0.0036 (13) −0.0038 (12) −0.0117 (15) C16′ 0.0456 (14) 0.0474 (16) 0.0326 (13) −0.0018 (13) 0.0192 (11) 0.0008 (12) C17′ 0.0283 (11) 0.0201 (10) 0.0180 (9) −0.0011 (8) 0.0032 (8) −0.0001 (8) C18′ 0.0294 (11) 0.0187 (10) 0.0206 (9) −0.0005 (9) 0.0044 (8) 0.0023 (8) C19′ 0.0327 (11) 0.0200 (10) 0.0192 (9) 0.0002 (9) 0.0027 (8) 0.0026 (8) C20′ 0.0249 (11) 0.0355 (13) 0.0281 (11) −0.0016 (10) 0.0052 (9) 0.0040 (10) C21′ 0.0312 (11) 0.0304 (12) 0.0216 (10) 0.0055 (10) 0.0017 (9) 0.0025 (9)

Geometric parameters (Å, º)

O1—C12 1.362 (3) O1′—C12′ 1.360 (3)

O1—C6 1.465 (2) O1′—C6′ 1.461 (3)

O2—C12 1.202 (3) O2′—C12′ 1.205 (3)

O3—C1 1.201 (3) O3′—C1′ 1.199 (3)

O4—C10 1.442 (2) O4′—C10′ 1.435 (3)

O4—C9 1.442 (3) O4′—C9′ 1.437 (3)

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Acta Cryst. (2002). E58, o874–o876

O7—C2 1.434 (3) O7′—C2′ 1.432 (3)

O7—C3 1.435 (3) O7′—C3′ 1.435 (4)

O8—C17 1.347 (2) O8′—C17′ 1.350 (3)

O8—C8 1.450 (2) O8′—C8′ 1.458 (2)

O9—C17 1.193 (3) O9′—C17′ 1.194 (3) O10—C18 1.436 (3) O10′—C18′ 1.440 (3) O10—C19 1.449 (3) O10′—C19′ 1.445 (3)

C1—C2 1.499 (3) C1′—C2′ 1.494 (4)

C1—C10 1.530 (3) C1′—C10′ 1.527 (3)

C2—C3 1.494 (3) C2′—C3′ 1.478 (4)

C2—H2 1.0000 C2′—H2′ 1.0000

C3—C4 1.487 (3) C3′—C4′ 1.493 (4)

C3—H3 1.0000 C3′—H3′ 1.0000

C4—C5 1.338 (3) C4′—C5′ 1.338 (3)

C4—C15 1.500 (3) C4′—C15′ 1.503 (4)

C5—C6 1.485 (3) C5′—C6′ 1.488 (3)

C5—H5 0.9500 C5′—H5′ 0.9500

C6—C7 1.547 (3) C6′—C7′ 1.545 (3)

C6—H6 1.0000 C6′—H6′ 1.0000

C7—C11 1.500 (3) C7′—C11′ 1.500 (3)

C7—C8 1.527 (3) C7′—C8′ 1.522 (3)

C7—H7 1.0000 C7′—H7′ 1.0000

C8—C9 1.517 (3) C8′—C9′ 1.513 (3)

C8—H8 1.0000 C8′—H8′ 1.0000

C9—C10 1.485 (3) C9′—C10′ 1.480 (3)

C9—H9 1.0000 C9′—H9′ 1.0000

C10—C14 1.514 (3) C10′—C14′ 1.507 (3) C11—C13 1.329 (3) C11′—C13′ 1.321 (3) C11—C12 1.488 (3) C11′—C12′ 1.486 (3)

C13—H13A 0.9500 C13′—H13C 0.9500

C13—H13B 0.9500 C13′—H13D 0.9500

C15—H15A 0.9800 C15′—H15D 0.9800

C15—H15B 0.9800 C15′—H15E 0.9800

C15—H15C 0.9800 C15′—H15F 0.9800

C16—H16A 0.9800 C16′—H16D 0.9800

C16—H16B 0.9800 C16′—H16E 0.9800

C16—H16C 0.9800 C16′—H16F 0.9800

C17—C18 1.509 (3) C17′—C18′ 1.516 (3) C18—C19 1.483 (3) C18′—C19′ 1.483 (3) C18—C20 1.506 (3) C18′—C20′ 1.502 (3) C19—C21 1.499 (4) C19′—C21′ 1.499 (3)

C19—H19 1.0000 C19′—H19′ 1.0000

C20—H20A 0.9800 C20′—H20D 0.9800

C20—H20B 0.9800 C20′—H20E 0.9800

C20—H20C 0.9800 C20′—H20F 0.9800

C21—H21A 0.9800 C21′—H21D 0.9800

C21—H21B 0.9800 C21′—H21E 0.9800

(10)

C12—O1—C6 109.82 (15) C12′—O1′—C6′ 110.15 (18) C10—O4—C9 61.98 (13) C10′—O4′—C9′ 62.02 (14) C14—O6—C16 114.27 (17) C14′—O6′—C16′ 116.2 (2) C2—O7—C3 62.74 (14) C2′—O7′—C3′ 62.09 (18) C17—O8—C8 117.91 (16) C17′—O8′—C8′ 118.14 (16) C18—O10—C19 61.88 (15) C18′—O10′—C19′ 61.87 (14) O3—C1—C2 118.98 (19) O3′—C1′—C2′ 118.8 (2) O3—C1—C10 120.39 (19) O3′—C1′—C10′ 119.9 (2) C2—C1—C10 120.64 (17) C2′—C1′—C10′ 121.2 (2) O7—C2—C3 58.68 (13) O7′—C2′—C3′ 59.07 (18) O7—C2—C1 120.14 (18) O7′—C2′—C1′ 120.6 (2) C3—C2—C1 121.80 (19) C3′—C2′—C1′ 122.1 (2)

O7—C2—H2 114.9 O7′—C2′—H2′ 114.6

C3—C2—H2 114.9 C3′—C2′—H2′ 114.6

C1—C2—H2 114.9 C1′—C2′—H2′ 114.6

O7—C3—C4 117.00 (18) O7′—C3′—C2′ 58.84 (18) O7—C3—C2 58.58 (14) O7′—C3′—C4′ 116.9 (2) C4—C3—C2 120.49 (18) C2′—C3′—C4′ 121.1 (2)

O7—C3—H3 116.1 O7′—C3′—H3′ 115.9

C4—C3—H3 116.1 C2′—C3′—H3′ 115.9

C2—C3—H3 116.1 C4′—C3′—H3′ 115.9

C5—C4—C3 118.57 (19) C5′—C4′—C3′ 118.4 (2) C5—C4—C15 126.4 (2) C5′—C4′—C15′ 126.3 (2) C3—C4—C15 114.88 (19) C3′—C4′—C15′ 115.2 (2) C4—C5—C6 125.48 (19) C4′—C5′—C6′ 126.5 (2)

C4—C5—H5 117.3 C4′—C5′—H5′ 116.7

C6—C5—H5 117.3 C6′—C5′—H5′ 116.7

O1—C6—H6 110.5 O1′—C6′—H6′ 110.1

C5—C6—H6 110.5 C5′—C6′—H6′ 110.1

C7—C6—H6 110.5 C7′—C6′—H6′ 110.1

C11—C7—C8 116.67 (17) C11′—C7′—C8′ 116.83 (18) C11—C7—C6 102.26 (16) C11′—C7′—C6′ 102.49 (18) C8—C7—C6 115.27 (16) C8′—C7′—C6′ 114.75 (17) C11—C7—H7 107.4 C11′—C7′—H7′ 107.4

C8—C7—H7 107.4 C8′—C7′—H7′ 107.4

C6—C7—H7 107.4 C6′—C7′—H7′ 107.4

O8—C8—H8 110.0 O8′—C8′—H8′ 110.3

C9—C8—H8 110.0 C9′—C8′—H8′ 110.3

C7—C8—H8 110.0 C7′—C8′—H8′ 110.3

(11)

supporting information

sup-8

Acta Cryst. (2002). E58, o874–o876

C10—C9—C8 127.58 (17) C10′—C9′—C8′ 127.83 (19)

O4—C9—H9 113.6 O4′—C9′—H9′ 113.6

C10—C9—H9 113.6 C10′—C9′—H9′ 113.6

C8—C9—H9 113.6 C8′—C9′—H9′ 113.6

(12)

C21—C19—H19 114.8 C21′—C19′—H19′ 114.4 C18—C20—H20A 109.5 C18′—C20′—H20D 109.5 C18—C20—H20B 109.5 C18′—C20′—H20E 109.5 H20A—C20—H20B 109.5 H20D—C20′—H20E 109.5 C18—C20—H20C 109.5 C18′—C20′—H20F 109.5 H20A—C20—H20C 109.5 H20D—C20′—H20F 109.5 H20B—C20—H20C 109.5 H20E—C20′—H20F 109.5 C19—C21—H21A 109.5 C19′—C21′—H21D 109.5 C19—C21—H21B 109.5 C19′—C21′—H21E 109.5 H21A—C21—H21B 109.5 H21D—C21′—H21E 109.5 C19—C21—H21C 109.5 C19′—C21′—H21F 109.5 H21A—C21—H21C 109.5 H21D—C21′—H21F 109.5 H21B—C21—H21C 109.5 H21E—C21′—H21F 109.5

(13)

supporting information

sup-10

Acta Cryst. (2002). E58, o874–o876