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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2015 Mar 21;71(Pt 4):o248. doi: 10.1107/S2056989015003965

Redetermination and absolute configuration of berkeleydione

Andrea Stierle a,*, Donald Stierle a, Daniel Decato a
PMCID: PMC4438833  PMID: 26029438

Abstract

The crystal structure of the title compound, berkeleydione [systematic name; (5aS,7R,9S,11R,11aS)-methyl 9-hy­droxy-1,1,5,7,9,11a-hexa­methyl-14-methyl­idene-3,8,10-trioxo-1,3,4,5a,6,7,8,9,10,11,11a,12-dodeca­hydro-7,11-methano­cycloocta­[4,5]cyclo­hepta­[1,2-c]pyran-11-carboxyl­ate], C26H32O7, has been reported previously [Stierle et al. (2004 ▸). Org. Lett. 6, 1049–1052]. However, the absolute configuration could not be determined from the data collected with Mo Kα radiation and has now been determined by refinement of the Flack parameter with data collected using Cu Kα radiation. It is in agreement with the previous circular dichroism assignment, and the crystal packing is similar to that described previously.

Keywords: crystal structure, absolute structure, resonant scattering, Berkeley pit, helicity rule

Related literature  

For further information on the isolation and properties of berkeleydione and related compounds, see: Stierle et al. (2004 ▸, 2011 ▸). For the previous NMR and circular dichroism structure determination, see: Stierle et al. (2004 ▸).graphic file with name e-71-0o248-scheme1.jpg

Experimental  

Crystal data  

  • C26H32O7

  • M r = 456.51

  • Orthorhombic, Inline graphic

  • a = 9.1832 (6) Å

  • b = 14.5805 (9) Å

  • c = 17.5148 (11) Å

  • V = 2345.2 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.77 mm−1

  • T = 100 K

  • 0.1 × 0.1 × 0.1 mm

Data collection  

  • Bruker D8 Venture diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.646, T max = 0.754

  • 39170 measured reflections

  • 4814 independent reflections

  • 4533 reflections with I > 2σ(I)

  • R int = 0.051

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.034

  • wR(F 2) = 0.091

  • S = 1.06

  • 4814 reflections

  • 309 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.19 e Å−3

  • Absolute structure: Flack x determined using 1914 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

  • Absolute structure parameter: 0.07 (7)

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▸); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015003965/su5086sup1.cif

e-71-0o248-sup1.cif (1.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015003965/su5086Isup2.hkl

e-71-0o248-Isup2.hkl (264KB, hkl)
Click here for additional data file. (1.2MB, tif)

. DOI: 10.1107/S2056989015003965/su5086fig1.tif

Mol­ecular structure of the title compound with atom labelling. Displacement ellipsoides aredrawn at the 50% probability level. Hydrogen atoms have been omitted for clarity.

CCDC reference: 1051259

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by grants from the National Science Foundation (NSF)-MRI (CHE-1337908) and the National Institute of Health (NIH) NIGMS P20GM103546.

supplementary crystallographic information

S1. Synthesis and crystallization

Clear prisms of the title compound were grown by slow evaporation of a solution in water and methanol at 245 K.

S2. Refinement

All the H atoms were located in difference Fourier maps and the hydroxyl H atom was freely refined. The C-bound H atoms were included in calculated positions and refined using a riding model: C—H = 0.98 - 1.00 Å with Uiso(H) = 1.5Ueq(C) for the methyl H atoms and = 1.2Ueq(C) for the other H atoms.

S3. Comment

The structure of berkeleydione, determined by detailed analysis of MS and NMR data has been reported (Stierle et al., 2004). The X-ray structure was also determined but the absolute configuration could not be determined from the MoKα data collected. The helicity rule of circular dichroism for cisoid homoannular dienes (Stierle et al., 2011) was applied to determine the absolute configuration of berkeleydione. The absolute configuration has now been determined by X-ray by refinement of the Flack parameter with data collected using CuKα radiation. This absolute configuration was shown to be the same as that determined with the helicity rule.

Figures

Fig. 1.

Fig. 1.

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Molecular structure of the title compound with atom labelling. Displacement ellipsoides aredrawn at the 50% probability level. Hydrogen atoms have been omitted for clarity.

Crystal data

C26H32O7 Dx = 1.293 Mg m−3
Mr = 456.51 Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121 Cell parameters from 9233 reflections
a = 9.1832 (6) Å θ = 3.9–74.7°
b = 14.5805 (9) Å µ = 0.77 mm−1
c = 17.5148 (11) Å T = 100 K
V = 2345.2 (3) Å3 Prism, colourless
Z = 4 0.1 × 0.1 × 0.1 mm
F(000) = 976
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Data collection

Bruker D8 Venture diffractometer 4814 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµus 4533 reflections with I > 2σ(I)
Double Bounce Multilayer Mirror monochromator Rint = 0.051
Detector resolution: 10.5 pixels mm-1 θmax = 74.8°, θmin = 4.0°
ω and φ scans h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009) k = −18→18
Tmin = 0.646, Tmax = 0.754 l = −21→21
39170 measured reflections
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Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.034 H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0569P)2 + 0.2309P] where P = (Fo2 + 2Fc2)/3
S = 1.06 (Δ/σ)max < 0.001
4814 reflections Δρmax = 0.20 e Å−3
309 parameters Δρmin = −0.19 e Å−3
0 restraints Absolute structure: Flack x determined using 1914 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods Absolute structure parameter: 0.07 (7)
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.83088 (19) 0.23759 (10) 0.57687 (9) 0.0347 (4)
O2 0.89494 (17) 0.30771 (9) 0.47209 (8) 0.0285 (3)
O3 0.8155 (2) 0.76251 (12) 0.40185 (9) 0.0419 (4)
O4 0.66301 (16) 0.56275 (9) 0.22151 (8) 0.0281 (3)
O5 0.69193 (19) 0.77820 (9) 0.23618 (9) 0.0317 (3)
O6 0.26938 (18) 0.55485 (13) 0.23397 (10) 0.0431 (4)
O7 0.40659 (17) 0.65832 (10) 0.17368 (9) 0.0325 (3)
C1 0.8103 (2) 0.30106 (13) 0.53388 (11) 0.0263 (4)
C2 0.6911 (2) 0.36998 (14) 0.54887 (11) 0.0283 (4)
H2A 0.7163 0.4042 0.5959 0.034*
H2B 0.6000 0.3359 0.5593 0.034*
C3 0.6607 (2) 0.43885 (13) 0.48639 (11) 0.0242 (4)
C4 0.5814 (2) 0.51480 (14) 0.49700 (11) 0.0256 (4)
C5 0.5717 (2) 0.58423 (13) 0.43178 (11) 0.0231 (4)
H5A 0.6701 0.5848 0.4074 0.028*
C6 0.5449 (2) 0.68248 (14) 0.45934 (11) 0.0286 (4)
H6A 0.6173 0.6985 0.4990 0.034*
H6B 0.4467 0.6868 0.4824 0.034*
C7 0.5568 (3) 0.75115 (14) 0.39198 (11) 0.0300 (5)
C8 0.7131 (3) 0.74107 (14) 0.36265 (12) 0.0303 (5)
C9 0.7363 (2) 0.70236 (14) 0.28192 (11) 0.0267 (4)
C10 0.6291 (2) 0.62327 (12) 0.26507 (11) 0.0223 (4)
C11 0.4753 (2) 0.62691 (14) 0.30026 (11) 0.0244 (4)
C12 0.4637 (2) 0.55420 (14) 0.36813 (11) 0.0252 (4)
C13 0.5029 (2) 0.45512 (14) 0.34211 (12) 0.0281 (4)
H13A 0.4463 0.4116 0.3737 0.034*
H13B 0.4700 0.4475 0.2886 0.034*
C14 0.6610 (2) 0.42778 (12) 0.34624 (11) 0.0256 (4)
H14 0.7127 0.4174 0.3001 0.031*
C15 0.7308 (2) 0.41761 (12) 0.41267 (12) 0.0240 (4)
C16 0.8869 (2) 0.38926 (13) 0.42057 (11) 0.0272 (4)
C17 0.9756 (3) 0.46460 (15) 0.45895 (13) 0.0324 (5)
H17A 0.9326 0.4792 0.5087 0.049*
H17B 0.9752 0.5195 0.4267 0.049*
H17C 1.0760 0.4435 0.4661 0.049*
C18 0.9605 (3) 0.35696 (16) 0.34803 (13) 0.0377 (5)
H18A 1.0577 0.3334 0.3602 0.057*
H18B 0.9692 0.4084 0.3123 0.057*
H18C 0.9023 0.3082 0.3246 0.057*
C19 0.3075 (2) 0.55189 (18) 0.39963 (13) 0.0366 (5)
H19A 0.3050 0.5147 0.4462 0.055*
H19B 0.2423 0.5250 0.3614 0.055*
H19C 0.2757 0.6145 0.4114 0.055*
C20 0.3701 (2) 0.60662 (14) 0.23390 (13) 0.0290 (4)
C21 0.8924 (2) 0.67381 (16) 0.26896 (14) 0.0351 (5)
H21A 0.9055 0.6559 0.2155 0.053*
H21B 0.9159 0.6218 0.3022 0.053*
H21C 0.9572 0.7253 0.2808 0.053*
C22 0.4455 (2) 0.72279 (14) 0.33273 (11) 0.0284 (4)
C23 0.3275 (3) 0.77049 (16) 0.31622 (13) 0.0399 (5)
H23A 0.3083 0.8264 0.3422 0.048*
H23B 0.2618 0.7489 0.2784 0.048*
C24 0.5349 (3) 0.84908 (15) 0.42152 (14) 0.0449 (6)
H24A 0.5350 0.8919 0.3784 0.067*
H24B 0.6141 0.8649 0.4566 0.067*
H24C 0.4415 0.8531 0.4484 0.067*
C25 0.5110 (3) 0.53681 (16) 0.57273 (12) 0.0339 (5)
H25A 0.5036 0.4808 0.6034 0.051*
H25B 0.4134 0.5619 0.5640 0.051*
H25C 0.5703 0.5821 0.6000 0.051*
C26 0.3148 (3) 0.64775 (18) 0.10765 (13) 0.0379 (5)
H26A 0.3550 0.6834 0.0652 0.057*
H26B 0.2166 0.6698 0.1195 0.057*
H26C 0.3104 0.5828 0.0933 0.057*
H5 0.690 (3) 0.760 (2) 0.1879 (18) 0.048 (8)*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0492 (9) 0.0275 (7) 0.0272 (7) 0.0056 (7) −0.0029 (7) 0.0036 (6)
O2 0.0348 (8) 0.0230 (6) 0.0278 (7) 0.0035 (6) −0.0013 (6) 0.0001 (6)
O3 0.0490 (10) 0.0459 (9) 0.0308 (8) −0.0174 (8) −0.0085 (8) −0.0017 (7)
O4 0.0343 (8) 0.0247 (6) 0.0252 (7) −0.0003 (6) 0.0025 (6) −0.0005 (6)
O5 0.0476 (9) 0.0231 (6) 0.0242 (7) −0.0044 (6) −0.0031 (7) 0.0044 (6)
O6 0.0364 (9) 0.0530 (10) 0.0400 (9) −0.0150 (8) −0.0122 (7) 0.0104 (8)
O7 0.0357 (8) 0.0360 (8) 0.0258 (7) −0.0023 (7) −0.0060 (7) 0.0046 (6)
C1 0.0337 (10) 0.0222 (8) 0.0230 (9) −0.0024 (8) −0.0059 (8) −0.0010 (7)
C2 0.0351 (11) 0.0263 (9) 0.0235 (9) 0.0014 (8) 0.0006 (8) 0.0024 (7)
C3 0.0271 (10) 0.0242 (9) 0.0213 (9) −0.0037 (7) −0.0009 (7) 0.0016 (7)
C4 0.0268 (9) 0.0282 (9) 0.0218 (9) −0.0006 (7) 0.0022 (8) 0.0030 (7)
C5 0.0247 (10) 0.0246 (9) 0.0200 (9) 0.0011 (7) 0.0026 (7) 0.0012 (7)
C6 0.0385 (11) 0.0274 (10) 0.0200 (9) 0.0069 (9) 0.0018 (8) −0.0002 (8)
C7 0.0467 (13) 0.0212 (9) 0.0222 (9) 0.0053 (8) −0.0017 (9) −0.0012 (7)
C8 0.0443 (13) 0.0208 (8) 0.0256 (10) −0.0071 (8) −0.0054 (9) 0.0033 (7)
C9 0.0302 (10) 0.0260 (9) 0.0240 (9) −0.0068 (8) −0.0017 (8) 0.0043 (8)
C10 0.0274 (9) 0.0214 (8) 0.0181 (8) −0.0011 (7) −0.0015 (7) 0.0041 (7)
C11 0.0254 (9) 0.0236 (9) 0.0240 (9) 0.0004 (7) −0.0015 (8) 0.0034 (7)
C12 0.0236 (9) 0.0282 (9) 0.0239 (9) −0.0027 (8) 0.0005 (8) 0.0057 (7)
C13 0.0341 (11) 0.0235 (9) 0.0268 (10) −0.0079 (8) −0.0064 (8) 0.0033 (8)
C14 0.0376 (11) 0.0168 (8) 0.0225 (9) −0.0007 (8) 0.0000 (8) −0.0012 (7)
C15 0.0312 (10) 0.0178 (8) 0.0229 (9) −0.0014 (7) 0.0021 (8) 0.0001 (7)
C16 0.0337 (11) 0.0229 (9) 0.0251 (9) 0.0024 (8) 0.0024 (8) 0.0029 (7)
C17 0.0297 (10) 0.0307 (10) 0.0369 (11) −0.0045 (8) −0.0003 (9) 0.0036 (9)
C18 0.0438 (13) 0.0372 (11) 0.0322 (11) 0.0140 (10) 0.0081 (10) 0.0020 (9)
C19 0.0253 (10) 0.0499 (13) 0.0347 (11) −0.0023 (9) 0.0043 (9) 0.0141 (10)
C20 0.0286 (10) 0.0294 (9) 0.0290 (10) 0.0027 (8) −0.0018 (9) 0.0028 (8)
C21 0.0295 (11) 0.0421 (11) 0.0337 (11) −0.0071 (9) −0.0010 (9) 0.0067 (9)
C22 0.0368 (12) 0.0259 (9) 0.0226 (9) 0.0043 (8) 0.0030 (8) 0.0029 (7)
C23 0.0466 (14) 0.0412 (12) 0.0320 (11) 0.0167 (11) 0.0006 (10) 0.0003 (9)
C24 0.0781 (18) 0.0246 (10) 0.0319 (12) 0.0116 (11) −0.0072 (13) −0.0039 (9)
C25 0.0394 (12) 0.0370 (11) 0.0254 (10) 0.0078 (9) 0.0084 (9) 0.0056 (9)
C26 0.0374 (12) 0.0503 (13) 0.0259 (10) 0.0068 (10) −0.0070 (9) 0.0001 (9)
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Geometric parameters (Å, º)

O1—C1 1.208 (2) C12—C13 1.557 (3)
O2—C1 1.336 (3) C12—C19 1.537 (3)
O2—C16 1.494 (2) C13—H13A 0.9900
O3—C8 1.206 (3) C13—H13B 0.9900
O4—C10 1.207 (2) C13—C14 1.507 (3)
O5—C9 1.425 (2) C14—H14 0.9500
O5—H5 0.89 (3) C14—C15 1.337 (3)
O6—C20 1.194 (3) C15—C16 1.498 (3)
O7—C20 1.339 (3) C16—C17 1.524 (3)
O7—C26 1.439 (3) C16—C18 1.514 (3)
C1—C2 1.509 (3) C17—H17A 0.9800
C2—H2A 0.9900 C17—H17B 0.9800
C2—H2B 0.9900 C17—H17C 0.9800
C2—C3 1.511 (3) C18—H18A 0.9800
C3—C4 1.338 (3) C18—H18B 0.9800
C3—C15 1.476 (3) C18—H18C 0.9800
C4—C5 1.529 (3) C19—H19A 0.9800
C4—C25 1.510 (3) C19—H19B 0.9800
C5—H5A 1.0000 C19—H19C 0.9800
C5—C6 1.531 (3) C21—H21A 0.9800
C5—C12 1.555 (3) C21—H21B 0.9800
C6—H6A 0.9900 C21—H21C 0.9800
C6—H6B 0.9900 C22—C23 1.320 (3)
C6—C7 1.551 (3) C23—H23A 0.9500
C7—C8 1.531 (3) C23—H23B 0.9500
C7—C22 1.514 (3) C24—H24A 0.9800
C7—C24 1.532 (3) C24—H24B 0.9800
C8—C9 1.537 (3) C24—H24C 0.9800
C9—C10 1.545 (3) C25—H25A 0.9800
C9—C21 1.510 (3) C25—H25B 0.9800
C10—C11 1.542 (3) C25—H25C 0.9800
C11—C12 1.596 (3) C26—H26A 0.9800
C11—C20 1.540 (3) C26—H26B 0.9800
C11—C22 1.534 (3) C26—H26C 0.9800
C1—O2—C16 121.19 (15) C14—C13—H13B 108.0
C9—O5—H5 107.9 (19) C13—C14—H14 118.9
C20—O7—C26 115.23 (17) C15—C14—C13 122.23 (19)
O1—C1—O2 117.99 (19) C15—C14—H14 118.9
O1—C1—C2 121.03 (19) C3—C15—C16 113.24 (17)
O2—C1—C2 120.98 (17) C14—C15—C3 121.92 (19)
C1—C2—H2A 108.1 C14—C15—C16 124.76 (19)
C1—C2—H2B 108.1 O2—C16—C15 108.84 (16)
C1—C2—C3 116.77 (17) O2—C16—C17 106.30 (16)
H2A—C2—H2B 107.3 O2—C16—C18 103.70 (15)
C3—C2—H2A 108.1 C15—C16—C17 110.69 (17)
C3—C2—H2B 108.1 C15—C16—C18 115.82 (18)
C4—C3—C2 123.34 (18) C18—C16—C17 110.82 (19)
C4—C3—C15 122.18 (18) C16—C17—H17A 109.5
C15—C3—C2 114.43 (17) C16—C17—H17B 109.5
C3—C4—C5 118.42 (17) C16—C17—H17C 109.5
C3—C4—C25 122.07 (18) H17A—C17—H17B 109.5
C25—C4—C5 119.37 (17) H17A—C17—H17C 109.5
C4—C5—H5A 105.8 H17B—C17—H17C 109.5
C4—C5—C6 113.15 (16) C16—C18—H18A 109.5
C4—C5—C12 112.74 (16) C16—C18—H18B 109.5
C6—C5—H5A 105.8 C16—C18—H18C 109.5
C6—C5—C12 112.76 (16) H18A—C18—H18B 109.5
C12—C5—H5A 105.8 H18A—C18—H18C 109.5
C5—C6—H6A 109.5 H18B—C18—H18C 109.5
C5—C6—H6B 109.5 C12—C19—H19A 109.5
C5—C6—C7 110.66 (16) C12—C19—H19B 109.5
H6A—C6—H6B 108.1 C12—C19—H19C 109.5
C7—C6—H6A 109.5 H19A—C19—H19B 109.5
C7—C6—H6B 109.5 H19A—C19—H19C 109.5
C8—C7—C6 105.02 (17) H19B—C19—H19C 109.5
C8—C7—C24 109.0 (2) O6—C20—O7 123.4 (2)
C22—C7—C6 107.30 (18) O6—C20—C11 127.3 (2)
C22—C7—C8 112.11 (16) O7—C20—C11 109.24 (17)
C22—C7—C24 113.42 (19) C9—C21—H21A 109.5
C24—C7—C6 109.61 (17) C9—C21—H21B 109.5
O3—C8—C7 121.0 (2) C9—C21—H21C 109.5
O3—C8—C9 120.7 (2) H21A—C21—H21B 109.5
C7—C8—C9 118.28 (18) H21A—C21—H21C 109.5
O5—C9—C8 101.10 (16) H21B—C21—H21C 109.5
O5—C9—C10 106.84 (16) C7—C22—C11 112.51 (17)
O5—C9—C21 113.64 (17) C23—C22—C7 124.1 (2)
C8—C9—C10 111.18 (16) C23—C22—C11 123.1 (2)
C21—C9—C8 111.79 (18) C22—C23—H23A 120.0
C21—C9—C10 111.75 (17) C22—C23—H23B 120.0
O4—C10—C9 120.13 (18) H23A—C23—H23B 120.0
O4—C10—C11 120.94 (17) C7—C24—H24A 109.5
C11—C10—C9 118.79 (16) C7—C24—H24B 109.5
C10—C11—C12 109.63 (15) C7—C24—H24C 109.5
C20—C11—C10 105.44 (16) H24A—C24—H24B 109.5
C20—C11—C12 113.12 (16) H24A—C24—H24C 109.5
C22—C11—C10 110.06 (16) H24B—C24—H24C 109.5
C22—C11—C12 108.50 (16) C4—C25—H25A 109.5
C22—C11—C20 110.07 (17) C4—C25—H25B 109.5
C5—C12—C11 107.71 (15) C4—C25—H25C 109.5
C5—C12—C13 108.88 (16) H25A—C25—H25B 109.5
C13—C12—C11 112.50 (16) H25A—C25—H25C 109.5
C19—C12—C5 110.12 (17) H25B—C25—H25C 109.5
C19—C12—C11 110.13 (17) O7—C26—H26A 109.5
C19—C12—C13 107.49 (18) O7—C26—H26B 109.5
C12—C13—H13A 108.0 O7—C26—H26C 109.5
C12—C13—H13B 108.0 H26A—C26—H26B 109.5
H13A—C13—H13B 107.3 H26A—C26—H26C 109.5
C14—C13—C12 117.01 (16) H26B—C26—H26C 109.5
C14—C13—H13A 108.0
O1—C1—C2—C3 −171.76 (19) C9—C10—C11—C20 131.44 (17)
O2—C1—C2—C3 7.3 (3) C9—C10—C11—C22 12.8 (2)
O3—C8—C9—O5 −106.8 (2) C10—C11—C12—C5 64.23 (19)
O3—C8—C9—C10 140.1 (2) C10—C11—C12—C13 −55.8 (2)
O3—C8—C9—C21 14.4 (3) C10—C11—C12—C19 −175.66 (17)
O4—C10—C11—C12 77.8 (2) C10—C11—C20—O6 133.4 (2)
O4—C10—C11—C20 −44.2 (2) C10—C11—C20—O7 −47.7 (2)
O4—C10—C11—C22 −162.91 (17) C10—C11—C22—C7 −57.5 (2)
O5—C9—C10—O4 99.8 (2) C10—C11—C22—C23 129.0 (2)
O5—C9—C10—C11 −76.0 (2) C11—C12—C13—C14 88.1 (2)
C1—O2—C16—C15 −39.0 (2) C12—C5—C6—C7 −58.2 (2)
C1—O2—C16—C17 80.2 (2) C12—C11—C20—O6 13.6 (3)
C1—O2—C16—C18 −162.85 (18) C12—C11—C20—O7 −167.50 (16)
C1—C2—C3—C4 −165.57 (19) C12—C11—C22—C7 62.4 (2)
C1—C2—C3—C15 12.1 (3) C12—C11—C22—C23 −111.0 (2)
C2—C3—C4—C5 173.63 (18) C12—C13—C14—C15 67.9 (2)
C2—C3—C4—C25 −1.9 (3) C13—C14—C15—C3 −4.4 (3)
C2—C3—C15—C14 137.95 (19) C13—C14—C15—C16 179.03 (17)
C2—C3—C15—C16 −45.1 (2) C14—C15—C16—O2 −125.66 (19)
C3—C4—C5—C6 −152.62 (19) C14—C15—C16—C17 117.9 (2)
C3—C4—C5—C12 77.9 (2) C14—C15—C16—C18 −9.4 (3)
C3—C15—C16—O2 57.5 (2) C15—C3—C4—C5 −3.8 (3)
C3—C15—C16—C17 −59.0 (2) C15—C3—C4—C25 −179.4 (2)
C3—C15—C16—C18 173.82 (17) C16—O2—C1—O1 −173.54 (18)
C4—C3—C15—C14 −44.4 (3) C16—O2—C1—C2 7.3 (3)
C4—C3—C15—C16 132.5 (2) C19—C12—C13—C14 −150.45 (18)
C4—C5—C6—C7 172.39 (18) C20—C11—C12—C5 −178.42 (16)
C4—C5—C12—C11 −174.52 (16) C20—C11—C12—C13 61.6 (2)
C4—C5—C12—C13 −52.3 (2) C20—C11—C12—C19 −58.3 (2)
C4—C5—C12—C19 65.4 (2) C20—C11—C22—C7 −173.30 (17)
C5—C6—C7—C8 −61.0 (2) C20—C11—C22—C23 13.2 (3)
C5—C6—C7—C22 58.4 (2) C21—C9—C10—O4 −25.1 (3)
C5—C6—C7—C24 −178.0 (2) C21—C9—C10—C11 159.17 (17)
C5—C12—C13—C14 −31.2 (2) C22—C7—C8—O3 178.38 (19)
C6—C5—C12—C11 55.8 (2) C22—C7—C8—C9 −1.9 (2)
C6—C5—C12—C13 178.09 (16) C22—C11—C12—C5 −56.0 (2)
C6—C5—C12—C19 −64.3 (2) C22—C11—C12—C13 −175.99 (17)
C6—C7—C8—O3 −65.4 (2) C22—C11—C12—C19 64.1 (2)
C6—C7—C8—C9 114.26 (18) C22—C11—C20—O6 −107.9 (3)
C6—C7—C22—C11 −62.5 (2) C22—C11—C20—O7 71.0 (2)
C6—C7—C22—C23 110.9 (2) C24—C7—C8—O3 52.0 (3)
C7—C8—C9—O5 73.5 (2) C24—C7—C8—C9 −128.35 (18)
C7—C8—C9—C10 −39.6 (2) C24—C7—C22—C11 176.34 (19)
C7—C8—C9—C21 −165.25 (18) C24—C7—C22—C23 −10.3 (3)
C8—C7—C22—C11 52.3 (2) C25—C4—C5—C6 23.1 (3)
C8—C7—C22—C23 −134.3 (2) C25—C4—C5—C12 −106.4 (2)
C8—C9—C10—O4 −150.80 (18) C26—O7—C20—O6 0.2 (3)
C8—C9—C10—C11 33.5 (2) C26—O7—C20—C11 −178.71 (17)
C9—C10—C11—C12 −106.49 (19)
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Footnotes

Supporting information for this paper is available from the IUCr electronic archives (Reference: SU5086).

References

  1. Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
  2. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.
  3. Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. [DOI] [PMC free article] [PubMed]
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  7. Stierle, D. B., Stierle, A., Patacini, B., McIntyre, K., Girtsman, T. & Bolstad, E. (2011). J. Nat. Prod. 74, 2273–2277. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015003965/su5086sup1.cif

e-71-0o248-sup1.cif (1.1MB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015003965/su5086Isup2.hkl

e-71-0o248-Isup2.hkl (264KB, hkl)
Click here for additional data file. (1.2MB, tif)

. DOI: 10.1107/S2056989015003965/su5086fig1.tif

Mol­ecular structure of the title compound with atom labelling. Displacement ellipsoides aredrawn at the 50% probability level. Hydrogen atoms have been omitted for clarity.

CCDC reference: 1051259

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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