Acta Cryst.(2003). E59, o1867±o1868 DOI: 10.1107/S1600536803024796 Rebecca A. Sampsonet al. C20H30O4
o1867
organic papers
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Conformation of (±)-membrenone-C
Rebecca A. Sampson, Michael V. Perkins and Max R. Taylor*
School of Chemistry, Physics and Earth Sciences, The Flinders University of South Australia, GPO Box 2100, Adelaide, SA 5001, Australia
Correspondence e-mail: max.taylor@flinders.edu.au
Key indicators Single-crystal X-ray study T= 123 K
Mean(C±C) = 0.003 AÊ Rfactor = 0.040 wRfactor = 0.079
Data-to-parameter ratio = 10.0
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2003 International Union of Crystallography Printed in Great Britain ± all rights reserved
The conformation of (ÿ)-membrenone-C, (2S,20R,3S,30S
)-(1S)-2,20
-ethane-1,1-diylbis(6-ethyl-3,5-dimethyl-2,3-dihydro-4H-pyran-4-one), C20H30O4, in the solid state is found to be the same as that predicted in solution by1H NMR spectros-copy and nOe (nuclear Overhauser effect) correlations.
Comment
Membrenone-C was ®rst isolated as a natural product, along
with membrenone-A and membrenone-B, from a
Mediterranean mollusc Pleurobranchus membranaceus by Ciavatta et al. (1993). Subsequent synthesis of (ÿ )-membrenone-A and (ÿ)-membrenone-B by Sampson & Perkins (2002) indicated an apparent error in the sign of the optical rotation reported for natural membrenone-C in the original isolation paper (Ciavatta et al., 1993). It was thus concluded by Sampson & Perkins (2002) that the structure of natural membrenone-C is enantiomeric to that reported here for (ÿ)-membrenone-C. Both (+)- and (ÿ)-membrenone-C have since been synthesized by Marshall & Ellis (2003) and their stereochemical results are consistent with ours (Perkins & Sampson, 2001; Sampson & Perkins, 2002).
The crystal structure of (ÿ)-membrenone-C, (I), reveals that the two dihydropyran-4-one rings each have pseudo-equatorial and axial substituents at their two tetrahedral centres (Fig. 1). For the (2S,3S)-dihydropyran ring, both the methyl substituent and the larger alkyl group are in pseudo-equatorial positions. The (20R,30S)-dihydropyran ring,
however, has the large alkyl group in a pseudo-equatorial orientation but the methyl group is in a pseudo-axial position. The conformation about the central C1ÐC2 and C1ÐC20
bonds is shown to be such that the A 1,3 strain is minimized. The 1,3-syn pentane interactions present all involve at least one H atom and are thus expected to be small. All other possible staggered conformations about the C1ÐC2 and C1Ð C20bonds lead to 1,3-synpentane interactions of large
(non-H) groups. The interplanar angle between the dihydropyran rings is approximately 62. The above conformation is the
same as that determined in solution by1H NMR spectroscopy and nOe (nuclear Overhauser effect) correlations (Perkins & Sampson, 2001; Sampson, 2001). The observed coupling H3Ð H2 ofJ= 13.8 Hz is consistent with a dihedral angle close to
180, as expected for pseudo-diaxial H atoms
(pseudo-diequatorial alkyl groups). Similarly, the observed coupling H30ÐH20ofJ= 2.1 Hz is consistent with a dihedral angle close
to 60, as expected for a pseudo-axial to equatorial coupling
(pseudo-axial methyl and pseudo-equatorial alkyl group). The couplings H1ÐH2,J= 3.0 Hz and H1ÐH20,J= 10.2 Hz are
consistent with HCÐCH dihedral angles of 60 and
180, respectively. Corresponding values from the crystal
structure are listed in Table 1. Further evidence for this conformation in solution comes from the strong nOe correl-ation between H30and H2, showing that these two protons are
close in space (H30 H2 = 2.240 AÊ in the crystal). Other nOe
correlations consistent with this conformation were observed. This conformation is also predicted, by molecular modelling studies, to be the low energy conformer in solution (Sampson, 2001).
Experimental
The (ÿ)-membrenone-C used in this study was obtainedviaa short enantiocontrolled synthesis (Perkins & Sampson, 2001) and crystal-lized from ether.
Crystal data
C20H30O4
Mr= 334.46
Orthorhombic,P212121
a= 9.836 (3) AÊ b= 13.065 (4) AÊ c= 14.391 (4) AÊ V= 1849.3 (10) AÊ3
Z= 4
Dx= 1.201 Mg mÿ3
MoKradiation Cell parameters from 3123
re¯ections
= 2.6±25.1 = 0.08 mmÿ1
T= 123 (2) K Needle, colourless 0.750.120.11 mm
Data collection
BrukerP4/SMART CCD area-detector diffractometer
!scans
Absorption correction: none 12757 measured re¯ections 2294 independent re¯ections
1648 re¯ections withF2> 2(F2)
Rint= 0.07
max= 27.7
h=ÿ12!12 k=ÿ16!17 l=ÿ18!6
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.040
wR(F2) = 0.079
S= 1.20 2177 re¯ections 217 parameters
H-atom parameters not re®ned w= 1/[2(F
o2) + (0.02Fo2)2]1/2
(/)max< 0.001
max= 0.26 e AÊÿ3
min=ÿ0.33 e AÊÿ3
Table 1
Selected torsion angles ().
H2ÐC2ÐC3ÐH3 177
H2ÐC2ÐC1ÐH1 ÿ58 H2
0ÐC20ÐC30ÐH30 ÿ52
H20ÐC20ÐC1ÐH1 178
All re¯ections with F2 > 0 were included in the least-squares
re®nement. Friedel pairs (1725 pairs) were averaged owing to the lack of signi®cant anomalous scattering. H atom peaks were observed in a difference map but these atoms were placed at calculated positions (CÐH = 0.946±0.968 AÊ). Their coordinates were not re®ned but were recalculated several times during the re®nement.
Data collection:SMART(Bruker, 1999); cell re®nement:SMART; data reduction: SAINT(Bruker, 1999) and Xtal3.7ADDREF and
SORTRF (Hall et al., 2000); program(s) used to solve structure:
SIR97 (Altomareet al., 1999); program(s) used to re®ne structure:
Xtal3.7 CRYLSQ; molecular graphics: Xtal3.7; software used to prepare material for publication:Xtal3.7BONDLAandCIFIO.
We thank Dr Jan Wikaira of the University of Canterbury, Christchurch, New Zealand, for collecting the data, and the Australian Research Council for ®nancial support.
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.
Bruker (1999).SMARTandSAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Ciavatta, M. L., Trivellone, E., Villani, G. & Cimino, G. (1993).Tetrahedron Lett.34, 6791±6794.
Hall, S. R., du Boulay, D. J. & Olthof-Hazekamp, R. (2000). Editors.Xtal3.7 System. University of Western Australia, Perth: Lamb.
Marshall, J. A. & Ellis, K. C. (2003).Org. Lett.5, 1729±1732. Perkins, M. V. & Sampson, R. A. (2001).Org. Lett.3, 123±126.
Sampson, R. A. (2001). PhD thesis, The Flinders University of South Australia, Adelaide, Australia.
Sampson, R. A. & Perkins, M. V. (2002).Org. Lett.4, 1655±1658.
Figure 1
supporting information
sup-1 Acta Cryst. (2003). E59, o1867–o1868
supporting information
Acta Cryst. (2003). E59, o1867–o1868 [https://doi.org/10.1107/S1600536803024796]
Conformation of (
–
)-membrenone-C
Rebecca A. Sampson, Michael V. Perkins and Max R. Taylor
(2S,2′R,3S,3′S)-(1S)-2,2′-ethane-1,1-diylbis(6-ethyl-3,5-dimethyl-2,3-dihydro- 4H-pyran-4-one)
Crystal data
C20H30O4 Mr = 334.46
Orthorhombic, P212121 Hall symbol: p_2ac_2ab
a = 9.836 (3) Å
b = 13.065 (4) Å
c = 14.391 (4) Å
V = 1849.3 (10) Å3 Z = 4
F(000) = 728
Dx = 1.201 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 3123 reflections
θ = 2.6–25.1°
µ = 0.08 mm−1 T = 123 K Needle, colourless 0.75 × 0.12 × 0.11 mm
Data collection
Bruker P4 CCD area-detector diffractometer
Radiation source: sealed tube Graphite monochromator
ω scans
12757 measured reflections 2294 independent reflections
1648 reflections with F2 > 2σ(F2) Rint = 0.07
θmax = 27.7° h = −12→12
k = −16→17
l = −18→6
Refinement
Refinement on F2 R[F2 > 2σ(F2)] = 0.040 wR(F2) = 0.079 S = 1.20 2177 reflections 217 parameters
H-atom parameters not refined
w = 1/[σ2(F
o2) + (0.02Fo2)2]1/2 (Δ/σ)max = 0.0003
Δρmax = 0.26 e Å−3 Δρmin = −0.33 e Å−3
Special details
Experimental. A 1 mm diameter collimator was used.
Refinement. Refinement of F2 against reflections with F2>0. 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 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement Friedel related data were averaged because an attempt to refine a Flack parameter was unsuccessful.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
C1 0.7737 (3) 0.97960 (17) 0.70830 (14) 0.0241 (13)
C2′ 0.7483 (3) 0.89901 (17) 0.63256 (14) 0.0226 (13)
C3 0.7927 (2) 1.17478 (18) 0.73629 (14) 0.0248 (14)
C3′ 0.6243 (3) 0.91530 (17) 0.57182 (13) 0.0221 (13)
C4 0.8026 (3) 1.2748 (2) 0.68225 (15) 0.0255 (14)
C4′ 0.6040 (3) 0.82316 (19) 0.50883 (14) 0.0260 (14)
C5 0.8773 (3) 1.26960 (18) 0.59387 (14) 0.0239 (14)
C5′ 0.6524 (3) 0.72541 (19) 0.54290 (14) 0.0252 (14)
C6 0.9264 (2) 1.17911 (19) 0.56446 (13) 0.0244 (14)
C6′ 0.7073 (3) 0.71902 (19) 0.62872 (15) 0.0247 (14)
C7 0.6755 (3) 1.1768 (2) 0.80563 (15) 0.0348 (16)
C7′ 0.4931 (3) 0.93527 (19) 0.62545 (15) 0.0306 (15)
C8 0.9024 (3) 1.36845 (18) 0.54250 (16) 0.0349 (16)
C8′ 0.6251 (3) 0.63131 (19) 0.48516 (16) 0.0360 (16)
C9 1.0178 (3) 1.16186 (19) 0.48291 (15) 0.0300 (15)
C9′ 0.7450 (3) 0.62110 (17) 0.67683 (15) 0.0305 (15)
C10 0.9428 (3) 1.1174 (2) 0.39987 (16) 0.0407 (17)
C10′ 0.7649 (3) 0.62845 (18) 0.78042 (17) 0.0388 (16)
C11 0.8992 (3) 0.95350 (18) 0.76603 (15) 0.0315 (15)
O1 0.89603 (17) 1.08727 (12) 0.60472 (9) 0.0239 (9)
O1′ 0.73589 (17) 0.80256 (11) 0.68176 (9) 0.0246 (9)
O4 0.7559 (2) 1.35533 (12) 0.71207 (11) 0.0355 (11)
O4′ 0.54170 (18) 0.83307 (14) 0.43506 (10) 0.0369 (11)
H2 0.69634 1.10126 0.63704 0.02900*
H2′ 0.82189 0.90175 0.58980 0.02900*
H3 0.87252 1.16517 0.77258 0.03200*
H3′ 0.64284 0.97538 0.53690 0.02800*
H7a 0.68755 1.23257 0.84726 0.05200*
H7b 0.67375 1.11461 0.83928 0.05200*
H7c 0.59224 1.18522 0.77289 0.05200*
H7'a 0.42032 0.94509 0.58291 0.04600*
H7'b 0.50349 0.99545 0.66228 0.04600*
H7'c 0.47368 0.87888 0.66462 0.04600*
H9a 1.08761 1.11532 0.50063 0.03700*
H9b 1.05719 1.22521 0.46548 0.03700*
H9'a 0.82733 0.59700 0.65037 0.03800*
H9'b 0.67459 0.57270 0.66575 0.03800*
H10a 1.00447 1.10793 0.34993 0.06200*
H10b 0.87291 1.16360 0.38124 0.06200*
H10c 0.90333 1.05371 0.41639 0.06200*
H10'a 0.78858 0.56316 0.80435 0.05900*
H10'b 0.68328 0.65144 0.80868 0.05900*
H10'c 0.83602 0.67575 0.79330 0.05900*
H1 0.69787 0.97880 0.74954 0.03000*
H11a 0.89020 0.88609 0.79014 0.04800*
H11b 0.90722 1.00071 0.81578 0.04800*
H11c 0.97757 0.95717 0.72777 0.04800*
H8a 0.86329 1.36752 0.48239 0.05300*
supporting information
sup-3 Acta Cryst. (2003). E59, o1867–o1868
H8c 0.86381 1.42533 0.57655 0.05300*
H8'a 0.69304 0.57924 0.49619 0.05200*
H8'b 0.62681 0.64629 0.41960 0.05200*
H8'c 0.53836 0.60220 0.49937 0.05200*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.0325 (16) 0.0227 (13) 0.0170 (11) −0.0013 (12) −0.0022 (11) 0.0019 (10)
C2 0.0226 (15) 0.0225 (13) 0.0234 (12) 0.0007 (12) 0.0019 (11) 0.0026 (10)
C2′ 0.0284 (15) 0.0186 (13) 0.0209 (11) −0.0030 (12) 0.0020 (11) 0.0036 (10)
C3 0.0300 (15) 0.0244 (14) 0.0200 (11) −0.0009 (12) −0.0008 (10) −0.0015 (11)
C3′ 0.0281 (15) 0.0175 (13) 0.0207 (11) −0.0034 (12) −0.0005 (11) 0.0070 (10)
C4 0.0250 (16) 0.0250 (15) 0.0265 (12) −0.0020 (12) −0.0063 (11) 0.0001 (11)
C4′ 0.0250 (15) 0.0309 (15) 0.0222 (12) −0.0059 (13) 0.0023 (11) −0.0000 (11)
C5 0.0296 (15) 0.0209 (14) 0.0213 (11) −0.0014 (12) −0.0069 (11) 0.0020 (10)
C5′ 0.0274 (16) 0.0235 (15) 0.0247 (12) −0.0045 (12) 0.0006 (11) −0.0042 (11)
C6 0.0240 (14) 0.0284 (15) 0.0208 (12) −0.0048 (13) −0.0037 (10) 0.0024 (11)
C6′ 0.0234 (15) 0.0225 (14) 0.0282 (13) −0.0031 (12) 0.0045 (10) 0.0005 (11)
C7 0.0431 (18) 0.0277 (15) 0.0335 (14) 0.0001 (13) 0.0107 (12) −0.0012 (13)
C7′ 0.0302 (16) 0.0316 (16) 0.0300 (13) 0.0005 (13) −0.0028 (12) 0.0034 (12)
C8 0.0457 (19) 0.0313 (17) 0.0276 (13) −0.0063 (14) −0.0015 (13) 0.0007 (11)
C8′ 0.0419 (19) 0.0326 (17) 0.0335 (14) −0.0065 (14) −0.0008 (13) −0.0094 (11)
C9 0.0360 (17) 0.0291 (15) 0.0250 (12) −0.0074 (13) 0.0046 (11) −0.0016 (11)
C9′ 0.0342 (17) 0.0225 (14) 0.0347 (13) −0.0014 (13) 0.0035 (13) 0.0025 (11)
C10 0.055 (2) 0.0424 (18) 0.0251 (12) −0.0006 (15) 0.0001 (13) −0.0043 (12)
C10′ 0.055 (2) 0.0273 (15) 0.0340 (13) 0.0028 (15) −0.0055 (14) 0.0092 (11)
C11 0.0410 (18) 0.0259 (15) 0.0277 (13) −0.0002 (13) −0.0092 (13) 0.0021 (11)
O1 0.0302 (11) 0.0203 (9) 0.0213 (8) 0.0006 (8) 0.0043 (7) 0.0018 (7)
O1′ 0.0355 (11) 0.0177 (9) 0.0207 (8) −0.0001 (8) −0.0021 (7) 0.0022 (6)
O4 0.0465 (12) 0.0196 (10) 0.0402 (10) 0.0049 (10) 0.0059 (10) −0.0036 (8)
O4′ 0.0452 (12) 0.0415 (11) 0.0239 (9) −0.0006 (10) −0.0091 (8) −0.0004 (8)
Geometric parameters (Å, º)
C2—C3 1.520 (3) C7—H7c 0.951
C2—C1 1.532 (3) C7′—H7'a 0.951
C2—O1 1.447 (3) C7′—H7'b 0.954
C2—H2 0.950 C7′—H7'c 0.947
C2′—C3′ 1.516 (3) C8—H8a 0.947
C2′—C1 1.536 (3) C8—H8b 0.959
C2′—O1′ 1.451 (3) C8—H8c 0.968
C2′—H2′ 0.950 C8′—H8'a 0.967
C3—C4 1.524 (3) C8′—H8'b 0.964
C3—C7 1.525 (3) C8′—H8'c 0.956
C3—H3 0.952 C9—C10 1.520 (3)
C3′—C4′ 1.520 (3) C9—H9a 0.952
C3′—H3′ 0.950 C9′—C10′ 1.507 (3)
C4—C5 1.470 (3) C9′—H9'a 0.948
C4—O4 1.226 (3) C9′—H9'b 0.952
C4′—C5′ 1.448 (3) C10—H10a 0.948
C4′—O4′ 1.233 (3) C10—H10b 0.954
C5—C6 1.346 (3) C10—H10c 0.948
C5—C8 1.508 (3) C10′—H10'a 0.949
C5′—C6′ 1.351 (3) C10′—H10'b 0.949
C5′—C8′ 1.508 (3) C10′—H10'c 0.952
C6—C9 1.495 (3) C1—C11 1.527 (4)
C6—O1 1.366 (3) C1—H1 0.953
C6′—C9′ 1.501 (3) C11—H11a 0.951
C6′—O1′ 1.361 (3) C11—H11b 0.948
C7—H7a 0.951 C11—H11c 0.948
C7—H7b 0.946
C3—C2—C1 116.01 (17) H7'a—C7′—H7'c 109.7
C3—C2—O1 110.25 (19) H7'b—C7′—H7'c 109.4
C3—C2—H2 103.0 C5—C8—H8a 111.7
C1—C2—O1 105.81 (18) C5—C8—H8b 110.4
C1—C2—H2 108.2 C5—C8—H8c 110.2
O1—C2—H2 113.87 H8a—C8—H8b 109.0
C3′—C2′—C1 116.3 (2) H8a—C8—H8c 108.2
C3′—C2′—O1′ 109.6 (2) H8b—C8—H8c 107.2
C3′—C2′—H2′ 103.53 C5′—C8′—H8'a 111.1
C1—C2′—O1′ 105.24 (16) C5′—C8′—H8'b 111.8
C1—C2′—H2′ 108.1 C5′—C8′—H8'c 111.4
O1′—C2′—H2′ 114.4 H8'a—C8′—H8'b 107.0
C2—C3—C4 108.24 (17) H8'a—C8′—H8'c 107.6
C2—C3—C7 112.5 (2) H8'b—C8′—H8'c 107.8
C2—C3—H3 109.1 C6—C9—C10 112.5 (2)
C4—C3—C7 111.6 (2) C6—C9—H9a 108.6
C4—C3—H3 109.9 C6—C9—H9b 108.8
C7—C3—H3 105.49 C10—C9—H9a 108.4
C2′—C3′—C4′ 109.8 (2) C10—C9—H9b 108.9
C2′—C3′—C7′ 114.40 (17) H9a—C9—H9b 109.5
C2′—C3′—H3′ 105.5 C6′—C9′—C10′ 115.7 (2)
C4′—C3′—C7′ 109.0 (2) C6′—C9′—H9'a 108.0
C4′—C3′—H3′ 111.36 C6′—C9′—H9'b 108.0
C7′—C3′—H3′ 106.8 C10′—C9′—H9'a 107.9
C3—C4—C5 115.7 (2) C10′—C9′—H9'b 107.6
C3—C4—O4 122.2 (2) H9'a—C9′—H9'b 109.5
C5—C4—O4 122.0 (2) C9—C10—H10a 109.6
C3′—C4′—C5′ 116.95 (18) C9—C10—H10b 109.2
C3′—C4′—O4′ 119.7 (2) C9—C10—H10c 109.7
C5′—C4′—O4′ 123.2 (2) H10a—C10—H10b 109.3
C4—C5—C6 119.5 (2) H10a—C10—H10c 109.8
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sup-5 Acta Cryst. (2003). E59, o1867–o1868
C6—C5—C8 122.6 (2) C9′—C10′—H10'a 109.5
C4′—C5′—C6′ 119.7 (2) C9′—C10′—H10'b 109.5
C4′—C5′—C8′ 118.3 (2) C9′—C10′—H10'c 109.2
C6′—C5′—C8′ 121.6 (2) H10'a—C10′—H10'b 109.7
C5—C6—C9 126.5 (2) H10'a—C10′—H10'c 109.4
C5—C6—O1 124.0 (2) H10'b—C10′—H10'c 109.4
C9—C6—O1 109.4 (2) C2—C1—C2′ 111.24 (17)
C5′—C6′—C9′ 125.0 (2) C2—C1—C11 112.4 (2)
C5′—C6′—O1′ 123.1 (2) C2—C1—H1 106.6
C9′—C6′—O1′ 111.95 (18) C2′—C1—C11 111.4 (2)
C3—C7—H7a 109.3 C2′—C1—H1 107.9
C3—C7—H7b 109.5 C11—C1—H1 106.95
C3—C7—H7c 109.2 C1—C11—H11a 109.3
H7a—C7—H7b 109.8 C1—C11—H11b 109.4
H7a—C7—H7c 109.3 C1—C11—H11c 109.3
H7b—C7—H7c 109.7 H11a—C11—H11b 109.6
C3′—C7′—H7'a 109.5 H11a—C11—H11c 109.6
C3′—C7′—H7'b 109.3 H11b—C11—H11c 109.8
C3′—C7′—H7'c 109.8 C2—O1—C6 115.63 (17)
H7'a—C7′—H7'b 109.1 C2′—O1′—C6′ 116.12 (16)
C1—C2—C3—C4 178.2 (2) C3—C4—C5—C6 2.6 (3)
C1—C2—C3—C7 −58.0 (3) C3—C4—C5—C8 −173.9 (2)
C1—C2—C3—H3 58.6 O4—C4—C5—C6 180.0 (2)
O1—C2—C3—C4 58.0 (2) O4—C4—C5—C8 3.5 (4)
O1—C2—C3—C7 −178.26 (18) C3′—C4′—C5′—C6′ 2.6 (3)
O1—C2—C3—H3 −61.6 C3′—C4′—C5′—C8′ 175.8 (2)
H2—C2—C3—C4 −63.9 O4′—C4′—C5′—C6′ −173.1 (2)
H2—C2—C3—C7 59.9 O4′—C4′—C5′—C8′ 0.0 (4)
H2—C2—C3—H3 176.6 C4—C5—C6—C9 −172.3 (2)
C3—C2—C1—C2′ 174.8 (2) C4—C5—C6—O1 9.5 (4)
C3—C2—C1—C11 −59.5 (3) C8—C5—C6—C9 4.0 (4)
C3—C2—C1—H1 57.4 C8—C5—C6—O1 −174.2 (2)
O1—C2—C1—C2′ −62.7 (2) C4—C5—C8—H8a −120.4
O1—C2—C1—C11 63.0 (2) C4—C5—C8—H8b 118.2
O1—C2—C1—H1 179.94 C4—C5—C8—H8c −0.0
H2—C2—C1—C2′ 59.7 C6—C5—C8—H8a 63.3
H2—C2—C1—C11 −174.58 C6—C5—C8—H8b −58.1
H2—C2—C1—H1 −57.7 C6—C5—C8—H8c −176.4
C3—C2—O1—C6 −49.7 (2) C4′—C5′—C6′—C9′ 171.9 (2)
C1—C2—O1—C6 −175.86 (17) C4′—C5′—C6′—O1′ −8.6 (4)
H2—C2—O1—C6 65.5 C8′—C5′—C6′—C9′ −1.0 (4)
C1—C2′—C3′—C4′ −173.15 (19) C8′—C5′—C6′—O1′ 178.6 (2)
C1—C2′—C3′—C7′ −50.2 (3) C4′—C5′—C8′—H8'a 153.1
C1—C2′—C3′—H3′ 66.8 C4′—C5′—C8′—H8'b 33.7
O1′—C2′—C3′—C4′ −54.0 (2) C4′—C5′—C8′—H8'c −87.0
O1′—C2′—C3′—C7′ 68.9 (2) C6′—C5′—C8′—H8'a −33.9
H2′—C2′—C3′—C4′ 68.5 C6′—C5′—C8′—H8'c 86.0
H2′—C2′—C3′—C7′ −168.6 C5—C6—C9—C10 −104.1 (3)
H2′—C2′—C3′—H3′ −51.6 C5—C6—C9—H9a 135.8
C3′—C2′—C1—C2 −55.0 (3) C5—C6—C9—H9b 16.7
C3′—C2′—C1—C11 178.7 (2) O1—C6—C9—C10 74.3 (2)
C3′—C2′—C1—H1 61.6 O1—C6—C9—H9a −45.8
O1′—C2′—C1—C2 −176.5 (2) O1—C6—C9—H9b −164.9
O1′—C2′—C1—C11 57.2 (2) C5—C6—O1—C2 15.2 (3)
O1′—C2′—C1—H1 −59.9 C9—C6—O1—C2 −163.29 (18)
H2′—C2′—C1—C2 60.8 C5′—C6′—C9′—C10′ −162.5 (3)
H2′—C2′—C1—C11 −65.4 C5′—C6′—C9′—H9'a 76.5
H2′—C2′—C1—H1 177.5 C5′—C6′—C9′—H9'b −41.8
C3′—C2′—O1′—C6′ 51.7 (2) O1′—C6′—C9′—C10′ 18.0 (3)
C1—C2′—O1′—C6′ 177.5 (2) O1′—C6′—C9′—H9'a −103.1
H2′—C2′—O1′—C6′ −64.1 O1′—C6′—C9′—H9'b 138.6
C2—C3—C4—C5 −35.2 (3) C5′—C6′—O1′—C2′ −20.1 (3)
C2—C3—C4—O4 147.5 (2) C9′—C6′—O1′—C2′ 159.5 (2)
C7—C3—C4—C5 −159.5 (2) C6—C9—C10—H10a 179.8
C7—C3—C4—O4 23.1 (3) C6—C9—C10—H10b 60.2
H3—C3—C4—C5 83.8 C6—C9—C10—H10c −59.6
H3—C3—C4—O4 −93.5 H9a—C9—C10—H10a −60.0
C2—C3—C7—H7a −179.9 H9a—C9—C10—H10b −179.7
C2—C3—C7—H7b 59.9 H9a—C9—C10—H10c 60.6
C2—C3—C7—H7c −60.3 H9b—C9—C10—H10a 59.1
C4—C3—C7—H7a −58.0 H9b—C9—C10—H10b −60.6
C4—C3—C7—H7b −178.2 H9b—C9—C10—H10c 179.7
C4—C3—C7—H7c 61.6 C6′—C9′—C10′—H10'a −179.8
H3—C3—C7—H7a 61.3 C6′—C9′—C10′—H10'b 59.8
H3—C3—C7—H7b −58.9 C6′—C9′—C10′—H10'c −60.0
H3—C3—C7—H7c −179.1 H9'a—C9′—C10′—H10'a −58.8
C2′—C3′—C4′—C5′ 28.5 (3) H9'a—C9′—C10′—H10'b −179.1
C2′—C3′—C4′—O4′ −155.5 (2) H9'a—C9′—C10′—H10'c 61.0
C7′—C3′—C4′—C5′ −97.5 (2) H9'b—C9′—C10′—H10'a 59.3
C7′—C3′—C4′—O4′ 78.4 (3) H9'b—C9′—C10′—H10'b −61.0
H3′—C3′—C4′—C5′ 145.0 H9'b—C9′—C10′—H10'c 179.1
H3′—C3′—C4′—O4′ −39.1 C2—C1—C11—H11a 179.9
C2′—C3′—C7′—H7'a 179.7 C2—C1—C11—H11b 60.0
C2′—C3′—C7′—H7'b 60.1 C2—C1—C11—H11c −60.2
C2′—C3′—C7′—H7'c −59.9 C2′—C1—C11—H11a −54.4
C4′—C3′—C7′—H7'a −57.0 C2′—C1—C11—H11b −174.4
C4′—C3′—C7′—H7'b −176.5 C2′—C1—C11—H11c 65.4
C4′—C3′—C7′—H7'c 63.4 H1—C1—C11—H11a 63.2
H3′—C3′—C7′—H7'a 63.4 H1—C1—C11—H11b −56.7
H3′—C3′—C7′—H7'b −56.1 H1—C1—C11—H11c −176.9
