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Absolute configuration of 3β-acet-oxy-olean-11,12-aziridin-28,13-β-olide.
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PMID:  21754518     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The title compound, C(32)H(49)NO(4), has been isolated from the dichloro-methane extract of the stem bark of Garcinia atroviridis Griff. ex T. Anders. Rings A and B, B and C, and C and D are trans-fused, whereas rings D and E are cis-fused. Rings A, B, C and E have slightly distorted chair conformations, while ring D is most heavily distorted towards a half-chair conformation owing to the strain induced by the lactonization. The ester group attached to ring A is in an equatorial position.
Authors:
Wen Nee Tan; Keng Chong Wong; Melati Khairuddean; Madhukar Hemamalini; Hoong-Kun Fun
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Publication Detail:
Type:  Journal Article     Date:  2011-04-29
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Title:  Acta crystallographica. Section E, Structure reports online     Volume:  67     ISSN:  1600-5368     ISO Abbreviation:  Acta Crystallogr Sect E Struct Rep Online     Publication Date:  2011 May 
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Created Date:  2011-07-14     Completed Date:  2011-07-14     Revised Date:  2011-12-09    
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Nlm Unique ID:  101089178     Medline TA:  Acta Crystallogr Sect E Struct Rep Online     Country:  England    
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Languages:  eng     Pagination:  o1220     Citation Subset:  -    
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Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online
Journal ID (publisher-id): Acta Cryst. E
ISSN: 1600-5368
Publisher: International Union of Crystallography
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A full version of this article is available from Crystallography Journals Online.© Tan et al. 2011
open-access:
Received Day: 08 Month: 4 Year: 2011
Accepted Day: 20 Month: 4 Year: 2011
collection publication date: Day: 01 Month: 5 Year: 2011
Electronic publication date: Day: 29 Month: 4 Year: 2011
pmc-release publication date: Day: 29 Month: 4 Year: 2011
Volume: 67 Issue: Pt 5
First Page: o1220 Last Page: o1220
ID: 3089217
PubMed Id: 21754518
Publisher Id: is2699
DOI: 10.1107/S1600536811014875
Coden: ACSEBH
Publisher Item Identifier: S1600536811014875

Absolute configuration of 3β-acet­oxy­olean-11,12-aziridin-28,13-β-olide Alternate Title:C32H49NO4
Wen Nee Tana
Keng Chong Wonga
Melati Khairuddeana
Madhukar Hemamalinib
Hoong-Kun Funb*
aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Pulau Penang, Malaysia
bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence: Correspondence e-mail: hkfun@usm.my
Thomson Reuters ResearcherID: A-3561-2009.

Related literature

For details and applications of Garcinia atroviridis Griff. ex T. Anders, see: Permana et al. (2001); Amran et al. (2009). For bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).[Chemical Structure ID: scheme1]


Experimental
Crystal data

  • C32H49NO4
  • Mr = 511.72
  • Monoclinic,
  • a = 13.0197 (2) Å
  • b = 6.7460 (1) Å
  • c = 32.0674 (5) Å
  • β = 100.6452 (4)°
  • V = 2768.04 (7) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 0.62 mm−1
  • T = 100 K
  • 0.73 × 0.15 × 0.14 mm

Data collection

  • Bruker SMART APEX DUO CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009) Tmin = 0.659, Tmax = 0.917
  • 8407 measured reflections
  • 3061 independent reflections
  • 3050 reflections with I > 2σ(I)
  • Rint = 0.018

Refinement

  • R[F2 > 2σ(F2)] = 0.033
  • wR(F2) = 0.087
  • S = 1.02
  • 3061 reflections
  • 342 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.37 e Å−3
  • Absolute structure: Flack (1983), 721 Friedel pairs
  • Flack parameter: 0.1 (2)

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).


Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014875/is2699sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014875/is2699Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report


Notes

fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2699).

TWN, WKC and MK wish to acknowledge the research grant RU1001/PKIMIA/811129 provided by the Universiti Sains Malaysia, Penang, that has resulted in this article. TWN would like to thank USM for the award of a postgraduate fellowship. MH and HKF thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

supplementary crystallographic information
Comment

Garcinia atroviridis Griff. ex T. Anders. (Clusiaceae) is a medium-sized fruit tree which may be found growing wild or cultivated throughout Peninsular Malaysia (Permana et al., 2001). In folkloric medicine, it has been used as a postpartum medication agent as well as an agent to treat earache, throat irritation, cough, dandruff and some stomachache associated with pregnancy (Amran et al., 2009). In our research on this plant, the stem bark extracts of G. atroviridis were examined. The title compound (I), 3β-acetoxyolean-11,12-aziridin-28,13-β-olide, has been isolated from the dichloromethane extract.

The title molecule presented in Fig. 1 contains five six-membered rings, namely, A (C15–C20), B (C14/C15/C20–C23), C (C9/C8/C12–C14/C23), D (C2/C7–C11) and E (C2–C7). The ester group attached to ring A is in an equatorial position. The bond distances (Allen et al., 1987) and angles in (I) are as expected. Rings A/B, B/C and C/D are trans-fused, whereas rings D/E are cis-fused. Rings A, B, C and E have slightly distorted chair conformations, ring D being most heavily distorted towards a half-chair conformation due to the strain induced by the lactonization, as shown by the Cremer & Pople, (1975) parameters: [ring A: Q = 0.572 (2) Å, θ = 175.5 (2)° and φ = 325 (3)°; B: Q = 0.584 (2) Å, θ = 11.6 (2)° and f = 118.6 (10)°; C: Q = 0.574 (2) Å, θ = 46.9 (2)° and φ = 111.4 (3)°; D: Q = 0.629 (2) Å, θ = 166.06 (18)° and f = 236.5 (8); E: Q = 0.571 (2) Å, θ = 3.8 (2)° and f = 202 (4)°]. The absolute configurations of the natural product molecule were determined by the refinement of the Flack parameter to 0.1 (2). There are eleven chiral centres in the molecule. From the structure presented, these centers exhibit the following chiralities: C2 = S, C7 = R, C8 = S, C9 = S, C12 = S, C13 = S, C14 = R, C15 = S, C18 = S, C20 = R and C23 = R. There are no classical hydrogen bond, weak interaction, CgCg and C—H···π interactions in the crystal packing.

Experimental

Air-dried stem bark of G. atroviridis was ground and sequentially extracted in a Soxhlet apparatus with hexane, dichloromethane and methanol. The dichloromethane extract after concentration was subjected to silica gel column chromatography using a hexane-chloroform-ethylacetate-methanol gradient to afford 58 fractions (D1–D58). Fraction D8 was further fractionated with hexane-ethyl acetate gradient as the eluting solvent, to afford 25 sub-fractions (D8a–D8y). The solid from fractions D8c–D8d was recrystallized from ethanol to yield the title compound (m.p. 581–583 K) as a colourless crystalline solid.

Refinement

All hydrogen atoms were positioned geometrically (N—H = 0.88 Å and C—H = 0.98–1.0 Å) and were refined using a riding model, with Uiso(H) = 1.2Ueq(C). 721 Friedel pairs were used to determine the absolute configuration.

Figures
Crystal data
Data collection
Refinement
Special details
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, °)

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.
Amran, A. A., Zaiton, Z., Faizah, O. & Morat, P. (2009). Singapore Med. J.50, 295–299.
Bruker (2009). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Permana, D., Lajis, N. H., Mackeen, M. M., Ali, A. M., Aimi, N., Kitajima, M. & Takayama, H. (2001). J. Nat. Prod.64, 976–979.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Figures

[Figure ID: Fap1]
Fig. 1. 

The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms omitted for clarity.



Tables
[TableWrap ID: d1e230]
C32H49NO4 F(000) = 1120
Mr = 511.72 Dx = 1.228 Mg m3
Monoclinic, C2 Cu Kα radiation, λ = 1.54178 Å
Hall symbol: C 2y Cell parameters from 8407 reflections
a = 13.0197 (2) Å θ = 4.2–62.5°
b = 6.7460 (1) Å µ = 0.62 mm1
c = 32.0674 (5) Å T = 100 K
β = 100.6452 (4)° Block, colourless
V = 2768.04 (7) Å3 0.73 × 0.15 × 0.14 mm
Z = 4

[TableWrap ID: d1e352]
Bruker SMART APEX DUO CCD area-detector diffractometer 3061 independent reflections
Radiation source: fine-focus sealed tube 3050 reflections with I > 2σ(I)
graphite Rint = 0.018
φ and ω scans θmax = 62.5°, θmin = 4.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009) h = −14→14
Tmin = 0.659, Tmax = 0.917 k = −7→5
8407 measured reflections l = −36→36

[TableWrap ID: d1e469]
Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033 H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0534P)2 + 1.724P] where P = (Fo2 + 2Fc2)/3
S = 1.02 (Δ/σ)max = 0.001
3061 reflections Δρmax = 0.32 e Å3
342 parameters Δρmin = −0.37 e Å3
1 restraint Absolute structure: Flack (1983), 721 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: 0.1 (2)

[TableWrap ID: d1e631]
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

[TableWrap ID: d1e685]
x y z Uiso*/Ueq
O1 0.32106 (11) −0.0737 (2) 0.17064 (4) 0.0246 (3)
O2 0.62607 (11) 0.4500 (2) 0.44068 (4) 0.0270 (4)
O3 0.67821 (13) 0.7573 (3) 0.42805 (4) 0.0378 (4)
O4 0.19103 (13) −0.2023 (3) 0.12291 (5) 0.0355 (4)
N1 0.55624 (13) 0.2185 (4) 0.21012 (6) 0.0339 (5)
H1 0.5937 0.3172 0.2030 0.041*
C1 0.24506 (16) −0.0616 (4) 0.13528 (6) 0.0246 (5)
C2 0.24394 (14) 0.1455 (3) 0.11795 (6) 0.0205 (4)
C3 0.21283 (15) 0.1641 (4) 0.06963 (6) 0.0218 (4)
H3A 0.1363 0.1478 0.0611 0.026*
H3B 0.2472 0.0582 0.0558 0.026*
C4 0.24546 (15) 0.3678 (4) 0.05499 (6) 0.0243 (5)
H4A 0.2039 0.4715 0.0661 0.029*
H4B 0.2283 0.3734 0.0236 0.029*
C5 0.36277 (16) 0.4152 (4) 0.06945 (6) 0.0256 (5)
C6 0.39041 (15) 0.4014 (4) 0.11863 (6) 0.0234 (5)
H6A 0.4663 0.4229 0.1283 0.028*
H6B 0.3525 0.5055 0.1314 0.028*
C7 0.36000 (15) 0.1978 (3) 0.13284 (6) 0.0196 (4)
H7A 0.3993 0.1012 0.1181 0.023*
C8 0.37372 (15) 0.1226 (3) 0.17907 (6) 0.0197 (4)
C9 0.31546 (14) 0.2417 (3) 0.20917 (5) 0.0169 (4)
C10 0.19759 (14) 0.2301 (4) 0.19046 (5) 0.0217 (4)
H10A 0.1599 0.3287 0.2049 0.026*
H10B 0.1713 0.0969 0.1961 0.026*
C11 0.17391 (14) 0.2695 (4) 0.14213 (5) 0.0214 (4)
H11A 0.1845 0.4120 0.1369 0.026*
H11B 0.0997 0.2377 0.1309 0.026*
C12 0.48492 (15) 0.0697 (4) 0.19851 (6) 0.0282 (5)
H12A 0.5131 −0.0480 0.1854 0.034*
C13 0.52441 (15) 0.0924 (4) 0.24330 (6) 0.0304 (6)
H13A 0.5763 −0.0087 0.2568 0.036*
C14 0.46077 (14) 0.1942 (3) 0.27216 (5) 0.0184 (4)
H14A 0.4692 0.3391 0.2672 0.022*
C15 0.50418 (14) 0.1640 (3) 0.32060 (6) 0.0194 (4)
C16 0.61602 (14) 0.2523 (4) 0.32994 (6) 0.0234 (5)
H16A 0.6639 0.1625 0.3183 0.028*
H16B 0.6158 0.3814 0.3153 0.028*
C17 0.65743 (15) 0.2823 (4) 0.37752 (6) 0.0243 (5)
H17A 0.6627 0.1528 0.3923 0.029*
H17B 0.7280 0.3423 0.3818 0.029*
C18 0.58362 (15) 0.4169 (3) 0.39561 (5) 0.0230 (5)
H18A 0.5801 0.5472 0.3805 0.028*
C19 0.47224 (15) 0.3357 (3) 0.39178 (6) 0.0222 (5)
C20 0.43358 (14) 0.2950 (3) 0.34356 (5) 0.0192 (4)
H20A 0.4339 0.4281 0.3299 0.023*
C21 0.31921 (14) 0.2264 (4) 0.33240 (5) 0.0218 (4)
H21A 0.3146 0.0843 0.3396 0.026*
H21B 0.2765 0.3026 0.3493 0.026*
C22 0.27630 (14) 0.2569 (4) 0.28508 (5) 0.0217 (4)
H22A 0.2741 0.4007 0.2788 0.026*
H22B 0.2038 0.2061 0.2785 0.026*
C23 0.34200 (14) 0.1521 (3) 0.25602 (6) 0.0183 (4)
C24 0.66861 (15) 0.6269 (3) 0.45241 (6) 0.0240 (5)
C25 0.7020 (2) 0.6407 (4) 0.49973 (7) 0.0368 (6)
H25A 0.6668 0.7533 0.5104 0.055*
H25B 0.7778 0.6598 0.5068 0.055*
H25C 0.6831 0.5182 0.5129 0.055*
C26 0.43081 (16) 0.2772 (4) 0.04793 (6) 0.0336 (6)
H26A 0.5047 0.3078 0.0582 0.050*
H26B 0.4140 0.2964 0.0171 0.050*
H26C 0.4171 0.1391 0.0547 0.050*
C27 0.38219 (18) 0.6281 (4) 0.05690 (6) 0.0342 (6)
H27A 0.4548 0.6647 0.0684 0.051*
H27B 0.3349 0.7174 0.0684 0.051*
H27C 0.3693 0.6391 0.0259 0.051*
C28 0.34752 (16) 0.4625 (3) 0.20954 (6) 0.0227 (5)
H28A 0.3000 0.5337 0.1873 0.034*
H28B 0.4192 0.4731 0.2043 0.034*
H28C 0.3438 0.5205 0.2372 0.034*
C29 0.51138 (16) −0.0556 (4) 0.33404 (6) 0.0255 (5)
H29A 0.5653 −0.0711 0.3595 0.038*
H29B 0.5296 −0.1362 0.3110 0.038*
H29C 0.4438 −0.0992 0.3401 0.038*
C30 0.40528 (17) 0.5014 (4) 0.40603 (6) 0.0296 (5)
H30A 0.4392 0.5506 0.4339 0.044*
H30B 0.3360 0.4490 0.4078 0.044*
H30C 0.3980 0.6101 0.3854 0.044*
C31 0.46755 (16) 0.1551 (4) 0.42054 (6) 0.0270 (5)
H31A 0.4845 0.1964 0.4503 0.040*
H31B 0.5181 0.0554 0.4150 0.040*
H31C 0.3971 0.0984 0.4146 0.040*
C32 0.31756 (17) −0.0706 (3) 0.25724 (6) 0.0246 (5)
H32A 0.3163 −0.1105 0.2865 0.037*
H32B 0.3716 −0.1460 0.2465 0.037*
H32C 0.2493 −0.0971 0.2395 0.037*

[TableWrap ID: d1e1786]
U11 U22 U33 U12 U13 U23
O1 0.0363 (8) 0.0157 (8) 0.0206 (6) 0.0029 (7) 0.0019 (5) −0.0023 (6)
O2 0.0373 (8) 0.0246 (9) 0.0164 (6) −0.0043 (7) −0.0025 (5) 0.0014 (6)
O3 0.0515 (9) 0.0313 (10) 0.0270 (7) −0.0149 (9) −0.0024 (6) 0.0025 (8)
O4 0.0508 (9) 0.0236 (10) 0.0292 (7) −0.0085 (8) 0.0001 (7) −0.0039 (7)
N1 0.0171 (8) 0.0479 (14) 0.0367 (9) −0.0027 (9) 0.0048 (7) −0.0081 (10)
C1 0.0309 (10) 0.0235 (13) 0.0194 (9) −0.0020 (10) 0.0045 (7) −0.0024 (9)
C2 0.0205 (9) 0.0193 (11) 0.0212 (9) 0.0002 (9) 0.0024 (7) −0.0009 (9)
C3 0.0224 (9) 0.0237 (12) 0.0180 (9) −0.0003 (9) 0.0001 (7) −0.0030 (8)
C4 0.0265 (10) 0.0295 (13) 0.0157 (8) −0.0002 (10) 0.0008 (7) 0.0017 (9)
C5 0.0271 (10) 0.0305 (14) 0.0188 (9) −0.0020 (10) 0.0033 (7) 0.0029 (9)
C6 0.0196 (9) 0.0314 (14) 0.0185 (9) −0.0025 (9) 0.0017 (7) 0.0008 (9)
C7 0.0203 (9) 0.0213 (13) 0.0173 (8) 0.0031 (8) 0.0038 (7) −0.0021 (8)
C8 0.0231 (9) 0.0150 (12) 0.0210 (9) 0.0025 (9) 0.0043 (7) −0.0018 (8)
C9 0.0182 (9) 0.0143 (11) 0.0183 (8) 0.0028 (8) 0.0035 (7) −0.0014 (8)
C10 0.0199 (9) 0.0254 (12) 0.0200 (9) 0.0040 (9) 0.0043 (7) −0.0003 (9)
C11 0.0185 (8) 0.0236 (12) 0.0205 (9) 0.0019 (9) −0.0003 (7) −0.0001 (9)
C12 0.0246 (10) 0.0370 (15) 0.0241 (10) 0.0137 (11) 0.0074 (8) −0.0003 (10)
C13 0.0234 (9) 0.0482 (17) 0.0193 (9) 0.0122 (11) 0.0035 (8) −0.0008 (10)
C14 0.0198 (9) 0.0177 (12) 0.0177 (8) 0.0022 (8) 0.0036 (7) −0.0008 (8)
C15 0.0205 (9) 0.0210 (12) 0.0163 (8) 0.0031 (9) 0.0025 (7) −0.0002 (8)
C16 0.0205 (9) 0.0301 (13) 0.0195 (9) 0.0031 (9) 0.0034 (7) 0.0017 (9)
C17 0.0225 (9) 0.0295 (13) 0.0195 (9) −0.0016 (10) 0.0006 (7) 0.0038 (9)
C18 0.0318 (10) 0.0221 (13) 0.0135 (8) −0.0025 (10) −0.0005 (7) 0.0010 (9)
C19 0.0280 (10) 0.0217 (12) 0.0176 (9) 0.0017 (9) 0.0059 (7) −0.0002 (8)
C20 0.0224 (9) 0.0182 (12) 0.0172 (8) 0.0023 (9) 0.0041 (7) 0.0020 (8)
C21 0.0217 (9) 0.0256 (12) 0.0194 (9) 0.0003 (9) 0.0072 (7) −0.0019 (9)
C22 0.0193 (8) 0.0243 (12) 0.0216 (9) 0.0035 (9) 0.0042 (7) −0.0007 (9)
C23 0.0194 (9) 0.0168 (11) 0.0191 (9) 0.0013 (8) 0.0044 (7) −0.0022 (8)
C24 0.0228 (9) 0.0257 (13) 0.0228 (10) 0.0004 (10) 0.0019 (7) 0.0003 (10)
C25 0.0522 (13) 0.0316 (15) 0.0242 (10) −0.0048 (12) 0.0009 (9) −0.0020 (10)
C26 0.0277 (10) 0.0529 (18) 0.0213 (9) 0.0005 (12) 0.0069 (8) −0.0001 (11)
C27 0.0378 (11) 0.0404 (16) 0.0229 (10) −0.0111 (12) 0.0018 (9) 0.0070 (10)
C28 0.0300 (10) 0.0180 (12) 0.0192 (9) 0.0017 (9) 0.0021 (7) −0.0006 (9)
C29 0.0321 (10) 0.0210 (12) 0.0213 (9) 0.0071 (10) −0.0005 (8) −0.0009 (9)
C30 0.0349 (11) 0.0317 (15) 0.0215 (9) 0.0058 (10) 0.0038 (8) −0.0042 (9)
C31 0.0317 (10) 0.0299 (13) 0.0195 (9) −0.0041 (10) 0.0053 (8) 0.0015 (9)
C32 0.0342 (11) 0.0181 (12) 0.0210 (9) −0.0048 (10) 0.0033 (8) 0.0016 (9)

[TableWrap ID: d1e2477]
O1—C1 1.363 (2) C15—C20 1.555 (3)
O1—C8 1.493 (3) C16—C17 1.535 (2)
O2—C24 1.340 (3) C16—H16A 0.9900
O2—C18 1.466 (2) C16—H16B 0.9900
O3—C24 1.198 (3) C17—C18 1.514 (3)
O4—C1 1.204 (3) C17—H17A 0.9900
N1—C12 1.371 (3) C17—H17B 0.9900
N1—C13 1.480 (3) C18—C19 1.534 (3)
N1—H1 0.8800 C18—H18A 1.0000
C1—C2 1.502 (3) C19—C31 1.536 (3)
C2—C3 1.533 (2) C19—C30 1.538 (3)
C2—C7 1.539 (3) C19—C20 1.560 (2)
C2—C11 1.547 (3) C20—C21 1.537 (2)
C3—C4 1.537 (3) C20—H20A 1.0000
C3—H3A 0.9900 C21—C22 1.531 (2)
C3—H3B 0.9900 C21—H21A 0.9900
C4—C5 1.546 (3) C21—H21B 0.9900
C4—H4A 0.9900 C22—C23 1.547 (3)
C4—H4B 0.9900 C22—H22A 0.9900
C5—C27 1.525 (4) C22—H22B 0.9900
C5—C26 1.534 (3) C23—C32 1.538 (3)
C5—C6 1.554 (2) C24—C25 1.502 (3)
C6—C7 1.522 (3) C25—H25A 0.9800
C6—H6A 0.9900 C25—H25B 0.9800
C6—H6B 0.9900 C25—H25C 0.9800
C7—C8 1.546 (2) C26—H26A 0.9800
C7—H7A 1.0000 C26—H26B 0.9800
C8—C12 1.510 (3) C26—H26C 0.9800
C8—C9 1.557 (2) C27—H27A 0.9800
C9—C10 1.543 (2) C27—H27B 0.9800
C9—C28 1.546 (3) C27—H27C 0.9800
C9—C23 1.597 (2) C28—H28A 0.9800
C10—C11 1.546 (2) C28—H28B 0.9800
C10—H10A 0.9900 C28—H28C 0.9800
C10—H10B 0.9900 C29—H29A 0.9800
C11—H11A 0.9900 C29—H29B 0.9800
C11—H11B 0.9900 C29—H29C 0.9800
C12—C13 1.442 (3) C30—H30A 0.9800
C12—H12A 1.0000 C30—H30B 0.9800
C13—C14 1.516 (3) C30—H30C 0.9800
C13—H13A 1.0000 C31—H31A 0.9800
C14—C23 1.563 (2) C31—H31B 0.9800
C14—C15 1.565 (2) C31—H31C 0.9800
C14—H14A 1.0000 C32—H32A 0.9800
C15—C29 1.541 (3) C32—H32B 0.9800
C15—C16 1.550 (3) C32—H32C 0.9800
C1—O1—C8 109.63 (16) C15—C16—H16B 109.0
C24—O2—C18 118.26 (16) H16A—C16—H16B 107.8
C12—N1—C13 60.61 (15) C18—C17—C16 109.20 (15)
C12—N1—H1 149.7 C18—C17—H17A 109.8
C13—N1—H1 149.7 C16—C17—H17A 109.8
O4—C1—O1 121.1 (2) C18—C17—H17B 109.8
O4—C1—C2 130.24 (18) C16—C17—H17B 109.8
O1—C1—C2 108.64 (18) H17A—C17—H17B 108.3
C1—C2—C3 115.65 (17) O2—C18—C17 108.59 (15)
C1—C2—C7 99.01 (16) O2—C18—C19 108.18 (14)
C3—C2—C7 110.84 (15) C17—C18—C19 114.38 (18)
C1—C2—C11 106.48 (16) O2—C18—H18A 108.5
C3—C2—C11 113.10 (16) C17—C18—H18A 108.5
C7—C2—C11 110.87 (16) C19—C18—H18A 108.5
C2—C3—C4 110.22 (16) C18—C19—C31 112.16 (16)
C2—C3—H3A 109.6 C18—C19—C30 107.22 (18)
C4—C3—H3A 109.6 C31—C19—C30 108.08 (16)
C2—C3—H3B 109.6 C18—C19—C20 105.63 (14)
C4—C3—H3B 109.6 C31—C19—C20 114.48 (18)
H3A—C3—H3B 108.1 C30—C19—C20 109.00 (16)
C3—C4—C5 114.01 (17) C21—C20—C15 110.54 (16)
C3—C4—H4A 108.8 C21—C20—C19 113.90 (14)
C5—C4—H4A 108.8 C15—C20—C19 117.30 (15)
C3—C4—H4B 108.8 C21—C20—H20A 104.5
C5—C4—H4B 108.8 C15—C20—H20A 104.5
H4A—C4—H4B 107.6 C19—C20—H20A 104.5
C27—C5—C26 108.38 (18) C22—C21—C20 110.53 (15)
C27—C5—C4 108.57 (18) C22—C21—H21A 109.5
C26—C5—C4 111.10 (18) C20—C21—H21A 109.5
C27—C5—C6 107.80 (18) C22—C21—H21B 109.5
C26—C5—C6 112.04 (17) C20—C21—H21B 109.5
C4—C5—C6 108.83 (15) H21A—C21—H21B 108.1
C7—C6—C5 109.49 (17) C21—C22—C23 113.23 (16)
C7—C6—H6A 109.8 C21—C22—H22A 108.9
C5—C6—H6A 109.8 C23—C22—H22A 108.9
C7—C6—H6B 109.8 C21—C22—H22B 108.9
C5—C6—H6B 109.8 C23—C22—H22B 108.9
H6A—C6—H6B 108.2 H22A—C22—H22B 107.7
C6—C7—C2 114.13 (17) C32—C23—C22 106.92 (17)
C6—C7—C8 126.37 (17) C32—C23—C14 111.44 (17)
C2—C7—C8 98.92 (15) C22—C23—C14 109.92 (15)
C6—C7—H7A 105.2 C32—C23—C9 112.57 (16)
C2—C7—H7A 105.2 C22—C23—C9 110.26 (16)
C8—C7—H7A 105.2 C14—C23—C9 105.77 (14)
O1—C8—C12 103.81 (17) O3—C24—O2 123.95 (18)
O1—C8—C7 98.61 (14) O3—C24—C25 124.6 (2)
C12—C8—C7 113.93 (15) O2—C24—C25 111.48 (19)
O1—C8—C9 108.06 (14) C24—C25—H25A 109.5
C12—C8—C9 113.95 (15) C24—C25—H25B 109.5
C7—C8—C9 116.24 (17) H25A—C25—H25B 109.5
C10—C9—C28 107.43 (17) C24—C25—H25C 109.5
C10—C9—C8 107.23 (15) H25A—C25—H25C 109.5
C28—C9—C8 109.88 (15) H25B—C25—H25C 109.5
C10—C9—C23 111.93 (15) C5—C26—H26A 109.5
C28—C9—C23 110.24 (16) C5—C26—H26B 109.5
C8—C9—C23 110.04 (16) H26A—C26—H26B 109.5
C9—C10—C11 112.39 (14) C5—C26—H26C 109.5
C9—C10—H10A 109.1 H26A—C26—H26C 109.5
C11—C10—H10A 109.1 H26B—C26—H26C 109.5
C9—C10—H10B 109.1 C5—C27—H27A 109.5
C11—C10—H10B 109.1 C5—C27—H27B 109.5
H10A—C10—H10B 107.9 H27A—C27—H27B 109.5
C10—C11—C2 112.49 (16) C5—C27—H27C 109.5
C10—C11—H11A 109.1 H27A—C27—H27C 109.5
C2—C11—H11A 109.1 H27B—C27—H27C 109.5
C10—C11—H11B 109.1 C9—C28—H28A 109.5
C2—C11—H11B 109.1 C9—C28—H28B 109.5
H11A—C11—H11B 107.8 H28A—C28—H28B 109.5
N1—C12—C13 63.43 (16) C9—C28—H28C 109.5
N1—C12—C8 119.3 (2) H28A—C28—H28C 109.5
C13—C12—C8 121.65 (17) H28B—C28—H28C 109.5
N1—C12—H12A 114.4 C15—C29—H29A 109.5
C13—C12—H12A 114.4 C15—C29—H29B 109.5
C8—C12—H12A 114.4 H29A—C29—H29B 109.5
C12—C13—N1 55.96 (15) C15—C29—H29C 109.5
C12—C13—C14 121.46 (17) H29A—C29—H29C 109.5
N1—C13—C14 115.9 (2) H29B—C29—H29C 109.5
C12—C13—H13A 116.5 C19—C30—H30A 109.5
N1—C13—H13A 116.5 C19—C30—H30B 109.5
C14—C13—H13A 116.5 H30A—C30—H30B 109.5
C13—C14—C23 109.54 (15) C19—C30—H30C 109.5
C13—C14—C15 114.15 (16) H30A—C30—H30C 109.5
C23—C14—C15 117.30 (15) H30B—C30—H30C 109.5
C13—C14—H14A 104.8 C19—C31—H31A 109.5
C23—C14—H14A 104.8 C19—C31—H31B 109.5
C15—C14—H14A 104.8 H31A—C31—H31B 109.5
C29—C15—C16 107.99 (18) C19—C31—H31C 109.5
C29—C15—C20 115.13 (16) H31A—C31—H31C 109.5
C16—C15—C20 107.86 (17) H31B—C31—H31C 109.5
C29—C15—C14 113.26 (16) C23—C32—H32A 109.5
C16—C15—C14 107.20 (15) C23—C32—H32B 109.5
C20—C15—C14 105.03 (15) H32A—C32—H32B 109.5
C17—C16—C15 112.80 (15) C23—C32—H32C 109.5
C17—C16—H16A 109.0 H32A—C32—H32C 109.5
C15—C16—H16A 109.0 H32B—C32—H32C 109.5
C17—C16—H16B 109.0
C8—O1—C1—O4 −178.70 (18) C12—N1—C13—C14 −111.9 (2)
C8—O1—C1—C2 0.5 (2) C12—C13—C14—C23 33.2 (3)
O4—C1—C2—C3 −33.0 (3) N1—C13—C14—C23 97.6 (2)
O1—C1—C2—C3 147.89 (16) C12—C13—C14—C15 167.0 (2)
O4—C1—C2—C7 −151.4 (2) N1—C13—C14—C15 −128.61 (18)
O1—C1—C2—C7 29.49 (19) C13—C14—C15—C29 −58.5 (2)
O4—C1—C2—C11 93.6 (2) C23—C14—C15—C29 71.6 (2)
O1—C1—C2—C11 −85.54 (19) C13—C14—C15—C16 60.5 (2)
C1—C2—C3—C4 −163.28 (17) C23—C14—C15—C16 −169.39 (18)
C7—C2—C3—C4 −51.7 (2) C13—C14—C15—C20 175.07 (19)
C11—C2—C3—C4 73.6 (2) C23—C14—C15—C20 −54.8 (2)
C2—C3—C4—C5 55.2 (2) C29—C15—C16—C17 −72.5 (2)
C3—C4—C5—C27 −174.19 (16) C20—C15—C16—C17 52.5 (2)
C3—C4—C5—C26 66.7 (2) C14—C15—C16—C17 165.10 (18)
C3—C4—C5—C6 −57.1 (2) C15—C16—C17—C18 −57.9 (3)
C27—C5—C6—C7 173.35 (17) C24—O2—C18—C17 106.1 (2)
C26—C5—C6—C7 −67.5 (2) C24—O2—C18—C19 −129.18 (19)
C4—C5—C6—C7 55.8 (2) C16—C17—C18—O2 −177.98 (17)
C5—C6—C7—C2 −57.1 (2) C16—C17—C18—C19 61.1 (2)
C5—C6—C7—C8 −179.84 (18) O2—C18—C19—C31 −52.2 (2)
C1—C2—C7—C6 177.12 (15) C17—C18—C19—C31 69.0 (2)
C3—C2—C7—C6 55.2 (2) O2—C18—C19—C30 66.3 (2)
C11—C2—C7—C6 −71.3 (2) C17—C18—C19—C30 −172.55 (16)
C1—C2—C7—C8 −46.17 (17) O2—C18—C19—C20 −177.56 (17)
C3—C2—C7—C8 −168.12 (18) C17—C18—C19—C20 −56.4 (2)
C11—C2—C7—C8 65.4 (2) C29—C15—C20—C21 −64.4 (2)
C1—O1—C8—C12 −147.48 (15) C16—C15—C20—C21 175.02 (16)
C1—O1—C8—C7 −30.11 (18) C14—C15—C20—C21 60.9 (2)
C1—O1—C8—C9 91.20 (17) C29—C15—C20—C19 68.5 (2)
C6—C7—C8—O1 175.33 (17) C16—C15—C20—C19 −52.1 (2)
C2—C7—C8—O1 46.32 (17) C14—C15—C20—C19 −166.21 (17)
C6—C7—C8—C12 −75.3 (3) C18—C19—C20—C21 −175.71 (18)
C2—C7—C8—C12 155.67 (19) C31—C19—C20—C21 60.4 (2)
C6—C7—C8—C9 60.2 (2) C30—C19—C20—C21 −60.8 (2)
C2—C7—C8—C9 −68.8 (2) C18—C19—C20—C15 53.0 (2)
O1—C8—C9—C10 −48.83 (19) C31—C19—C20—C15 −71.0 (2)
C12—C8—C9—C10 −163.63 (19) C30—C19—C20—C15 167.88 (18)
C7—C8—C9—C10 60.8 (2) C15—C20—C21—C22 −64.6 (2)
O1—C8—C9—C28 −165.30 (14) C19—C20—C21—C22 160.85 (18)
C12—C8—C9—C28 79.9 (2) C20—C21—C22—C23 56.1 (2)
C7—C8—C9—C28 −55.6 (2) C21—C22—C23—C32 74.7 (2)
O1—C8—C9—C23 73.13 (18) C21—C22—C23—C14 −46.4 (2)
C12—C8—C9—C23 −41.7 (2) C21—C22—C23—C9 −162.63 (17)
C7—C8—C9—C23 −177.21 (16) C13—C14—C23—C32 62.1 (2)
C28—C9—C10—C11 72.3 (2) C15—C14—C23—C32 −70.1 (2)
C8—C9—C10—C11 −45.8 (2) C13—C14—C23—C22 −179.53 (19)
C23—C9—C10—C11 −166.56 (18) C15—C14—C23—C22 48.3 (2)
C9—C10—C11—C2 49.1 (3) C13—C14—C23—C9 −60.5 (2)
C1—C2—C11—C10 45.1 (2) C15—C14—C23—C9 167.27 (17)
C3—C2—C11—C10 173.17 (18) C10—C9—C23—C32 63.8 (2)
C7—C2—C11—C10 −61.6 (2) C28—C9—C23—C32 −176.72 (16)
C13—N1—C12—C8 113.1 (2) C8—C9—C23—C32 −55.4 (2)
O1—C8—C12—N1 179.68 (16) C10—C9—C23—C22 −55.5 (2)
C7—C8—C12—N1 73.5 (2) C28—C9—C23—C22 64.0 (2)
C9—C8—C12—N1 −63.0 (2) C8—C9—C23—C22 −174.65 (16)
O1—C8—C12—C13 −105.2 (2) C10—C9—C23—C14 −174.31 (17)
C7—C8—C12—C13 148.7 (2) C28—C9—C23—C14 −54.80 (19)
C9—C8—C12—C13 12.1 (3) C8—C9—C23—C14 66.6 (2)
C8—C12—C13—N1 −109.5 (3) C18—O2—C24—O3 −3.3 (3)
N1—C12—C13—C14 101.7 (3) C18—O2—C24—C25 176.38 (17)
C8—C12—C13—C14 −7.8 (4)


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