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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o1927
https://doi.org/10.1107/S160053681002564X

14-De­oxyxyloccensin K from Chisocheton ceramicus (Meliaceae)

Ibrahim A. Najmuldeen,a Abdul Hamid Abdul Hadi,a Khalijah Awang,a Khalit Mohamadb and Seik Weng Nga*

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and bDepartment of Pharmacy, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 29 June 2010; accepted 29 June 2010; online 7 July 2010)

The title limonoid 14-de­oxyxyloccensin K, C27H34O7, isolated from Chisocheton ceramicus (Meliaceae), features an oxygen linkage between carbon-3 and carbon-8 along with a tetra­hydro­furyl sub-unit. The six-membered rings adopt chair configurations and the tetra­hydro­furyl sub-unit has an envelope shape.

Related literature

For the synthesis of 14-de­oxyxyloccensin K from xyloccensin K, see: Kim et al. (2004[Kim, J.-G., Cho, D. H. & Jang, D. O. (2004). Tetrahedron Lett. 45, 3031-3033.]). For the crystal structure of xyloccensin K, see: Kokpol et al. (1996[Kokpol, U., Chavasiri, W., Tip-Pyang, S., Veerachato, G., Zhao, F., Simpson, J. & Weavers, R. T. (1996). Phytochemistry, 41, 903-905.]). For a description of other xyloccensin limonoids, see: Wu et al. (2003[Wu, J., Zhang, S., Xiao, Q., Li, Q.-X., Huang, J.-S., Xiao, Z.-H. & Long, L.-J. (2003). Z. Naturforsch. Teil B, 58, 1216-1219.]).

[Scheme 1]

Experimental

Crystal data

  • C27H34O7

  • Mr = 470.54

  • Orthorhombic, P 21 21 21

  • a = 8.7174 (6) Å

  • b = 11.7401 (8) Å

  • c = 23.1106 (16) Å

  • V = 2365.2 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.25 × 0.15 × 0.05 mm
Data collection

  • Bruker SMART APEX diffractometer

  • 22814 measured reflections

  • 3083 independent reflections

  • 2674 reflections with I > 2σ(I)

  • Rint = 0.053
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.098

  • S = 1.03

  • 3083 reflections

  • 307 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681002564X/bt5284sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681002564X/bt5284Isup2.hkl

checkCIF report


Comment top

The limonoid, xyloccensin K, which was isolated from the seeds of Xylocarpus granatum, has a structure similar to those of other limonoids but it features an ether linkage connecting the C3 and C8 atoms along with a tetrahydrofuryl sub-unit (Kokpol et al., 1996). As the compound is also a tertiary alcohol, the compound can also be deoxygenated by a free-radical process (Kim et al., 2004). The synthetic compound was fully characterized by spectroscopic methods. This deoxygenated compound (Scheme I, Fig. 1) was isolated from the bark of Chisocheton ceramicus in the present study; the spectroscopic assignments are confirmed by the crystal structure determination.

Related literature top

For the synthesis of 14-deoxyxyloccensin K from xyloccensin K, see: Kim et al. (2004). For the crystal structure of xyloccensin K, see: Kokpol et al. (1996). For a description of other xyloccensin limonoids, see: Wu et al. (2003).

Experimental top

The bark of C. ceramicine (900 g), collected in Kedah, Peninsular Malaysia, was dried, ground, and extracted successively with methanol. The extract (200 g) was partitioned with 10% aqueous methanol and ethyl acetate. The ethyl acetate-soluble fraction (10 g) was subjected to silica gel column-chromatography (hexane/ethyl acetate 1:0 to 0:1). The fraction eluted with hexane/ethyl acetate (2:8) was purified on a silica gel column (ethyl acetate:acetone:hexane 65:10:25). Further HPLC purification followed by recrystallization from aqueous methanol yielded colorless crystals.

Refinement top

H-atoms were placed in calculated positions (C—H 0.95 to 1.00 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).

The absolute configuration was set to that of xyloccensin K, which was isolated from the seeds of Xylocarpus granatum (Kokpol et al., 1996).

2348 Friedel pairs were merged.

Structure description top

The limonoid, xyloccensin K, which was isolated from the seeds of Xylocarpus granatum, has a structure similar to those of other limonoids but it features an ether linkage connecting the C3 and C8 atoms along with a tetrahydrofuryl sub-unit (Kokpol et al., 1996). As the compound is also a tertiary alcohol, the compound can also be deoxygenated by a free-radical process (Kim et al., 2004). The synthetic compound was fully characterized by spectroscopic methods. This deoxygenated compound (Scheme I, Fig. 1) was isolated from the bark of Chisocheton ceramicus in the present study; the spectroscopic assignments are confirmed by the crystal structure determination.

For the synthesis of 14-deoxyxyloccensin K from xyloccensin K, see: Kim et al. (2004). For the crystal structure of xyloccensin K, see: Kokpol et al. (1996). For a description of other xyloccensin limonoids, see: Wu et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C27H34O7 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
(I) top
Crystal data top
C27H34O7F(000) = 1008
Mr = 470.54Dx = 1.321 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5382 reflections
a = 8.7174 (6) Åθ = 2.5–27.9°
b = 11.7401 (8) ŵ = 0.10 mm−1
c = 23.1106 (16) ÅT = 100 K
V = 2365.2 (3) Å3Triangular plate, colorless
Z = 40.25 × 0.15 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		2674 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
Graphite monochromatorθmax = 27.5°, θmin = 1.8°
ω scansh = −11→10
22814 measured reflectionsk = −15→15
3083 independent reflectionsl = −29→29
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0502P)2 + 0.7549P]
where P = (Fo2 + 2Fc2)/3
3083 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C27H34O7V = 2365.2 (3) Å3
Mr = 470.54Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.7174 (6) ŵ = 0.10 mm−1
b = 11.7401 (8) ÅT = 100 K
c = 23.1106 (16) Å0.25 × 0.15 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		2674 reflections with I > 2σ(I)
22814 measured reflectionsRint = 0.053
3083 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.03Δρmax = 0.29 e Å−3
3083 reflectionsΔρmin = −0.20 e Å−3
307 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7791 (2)0.99435 (15)0.16955 (8)0.0278 (4)
O20.34822 (19)0.79390 (12)0.19484 (7)0.0208 (4)
O30.1819 (2)0.65454 (13)0.19079 (8)0.0267 (4)
O40.20193 (19)0.82792 (12)0.31200 (6)0.0177 (3)
O50.5624 (2)1.06497 (15)0.44621 (7)0.0281 (4)
O60.4725 (2)1.10625 (17)0.53467 (8)0.0333 (5)
O7−0.0536 (2)0.96552 (15)0.46084 (8)0.0306 (4)
C10.6616 (3)0.9897 (2)0.20877 (11)0.0242 (5)
H10.66431.02320.24620.029*
C20.7301 (3)0.9356 (2)0.12191 (12)0.0280 (6)
H20.78880.92410.08780.034*
C30.5866 (3)0.8964 (2)0.13033 (11)0.0250 (5)
H30.52680.85370.10370.030*
C40.5416 (3)0.93121 (19)0.18712 (10)0.0199 (5)
C50.3928 (3)0.90631 (18)0.21706 (10)0.0181 (5)
H50.41530.89750.25920.022*
C60.2663 (3)0.99724 (19)0.21106 (10)0.0174 (5)
C70.1137 (3)0.94872 (18)0.23416 (10)0.0180 (5)
H70.03201.00600.22530.022*
C80.0746 (3)0.84036 (19)0.20019 (10)0.0199 (5)
H8A−0.01510.80330.21850.024*
H8B0.04480.86210.16040.024*
C90.2029 (3)0.75607 (19)0.19700 (10)0.0201 (5)
C100.2485 (3)1.0343 (2)0.14753 (11)0.0237 (5)
H10A0.34621.06480.13340.036*
H10B0.16921.09320.14470.036*
H10C0.21870.96850.12400.036*
C110.3102 (3)1.10229 (18)0.24743 (10)0.0196 (5)
H11A0.41141.13050.23430.024*
H11B0.23411.16330.24030.024*
C120.3179 (3)1.07930 (19)0.31233 (10)0.0204 (5)
H12A0.34101.15130.33290.024*
H12B0.40231.02510.32030.024*
C130.1678 (3)1.03012 (18)0.33536 (10)0.0187 (5)
H130.08951.09140.32980.022*
C140.1096 (3)0.92757 (18)0.29983 (10)0.0182 (5)
C15−0.0487 (3)0.8923 (2)0.32228 (10)0.0210 (5)
H15A−0.09790.83530.29670.025*
H15B−0.11760.95860.32710.025*
C16−0.0026 (3)0.8406 (2)0.38075 (10)0.0215 (5)
H16−0.08190.78750.39660.026*
C170.1497 (3)0.77978 (19)0.36585 (10)0.0196 (5)
H170.12920.69670.36020.024*
C180.2718 (3)0.79431 (19)0.41271 (10)0.0204 (5)
C190.3077 (3)0.92499 (19)0.42077 (10)0.0200 (5)
H190.39490.94280.39420.024*
C200.1715 (3)1.00645 (19)0.40270 (10)0.0202 (5)
C210.0274 (3)0.9414 (2)0.41994 (10)0.0221 (5)
C220.4198 (3)0.7342 (2)0.39397 (10)0.0238 (5)
H22A0.39970.65270.38880.036*
H22B0.49850.74460.42380.036*
H22C0.45590.76690.35740.036*
C230.2093 (3)0.7351 (2)0.46731 (10)0.0269 (6)
H23A0.18940.65470.45880.040*
H23B0.11380.77210.47940.040*
H23C0.28510.74080.49850.040*
C240.1745 (3)1.1215 (2)0.43403 (11)0.0249 (5)
H24A0.08771.16800.42110.037*
H24B0.27071.16100.42520.037*
H24C0.16711.10900.47590.037*
C250.3663 (3)0.9470 (2)0.48241 (10)0.0245 (5)
H25A0.27620.95550.50810.029*
H25B0.42300.87850.49540.029*
C260.4692 (3)1.0497 (2)0.49100 (10)0.0254 (5)
C270.6748 (3)1.1553 (2)0.45213 (12)0.0317 (6)
H27A0.73751.15920.41700.047*
H27B0.74091.13950.48550.047*
H27C0.62201.22810.45790.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0202 (9)0.0236 (9)0.0395 (10)−0.0015 (8)−0.0016 (8)0.0028 (8)
O20.0216 (9)0.0111 (7)0.0297 (9)−0.0028 (7)−0.0001 (7)−0.0013 (6)
O30.0285 (10)0.0143 (8)0.0372 (9)−0.0041 (8)−0.0022 (8)−0.0015 (7)
O40.0210 (9)0.0118 (7)0.0202 (7)0.0020 (6)−0.0004 (7)0.0014 (6)
O50.0338 (11)0.0255 (9)0.0250 (9)−0.0024 (9)−0.0002 (8)−0.0053 (7)
O60.0369 (12)0.0394 (11)0.0235 (9)−0.0049 (10)−0.0029 (9)−0.0100 (8)
O70.0355 (11)0.0244 (9)0.0319 (10)0.0036 (8)0.0113 (9)−0.0022 (7)
C10.0217 (12)0.0238 (12)0.0272 (12)−0.0006 (10)−0.0013 (10)0.0037 (10)
C20.0304 (15)0.0207 (12)0.0328 (13)0.0014 (11)0.0034 (11)−0.0013 (10)
C30.0263 (14)0.0197 (11)0.0290 (13)−0.0043 (10)0.0019 (11)−0.0025 (10)
C40.0211 (12)0.0140 (10)0.0248 (11)−0.0005 (9)−0.0033 (10)0.0020 (9)
C50.0214 (12)0.0101 (10)0.0228 (11)−0.0021 (9)−0.0019 (9)−0.0004 (8)
C60.0165 (11)0.0131 (10)0.0225 (11)−0.0015 (9)−0.0041 (9)0.0019 (9)
C70.0180 (12)0.0123 (10)0.0237 (11)−0.0006 (9)−0.0036 (9)0.0014 (8)
C80.0194 (12)0.0173 (11)0.0231 (12)−0.0026 (9)−0.0046 (9)−0.0013 (9)
C90.0241 (13)0.0169 (10)0.0191 (11)−0.0025 (9)−0.0024 (10)0.0014 (8)
C100.0268 (13)0.0189 (11)0.0255 (12)−0.0012 (10)−0.0043 (10)0.0044 (9)
C110.0219 (13)0.0097 (9)0.0272 (11)−0.0011 (9)−0.0026 (10)0.0025 (8)
C120.0237 (12)0.0130 (10)0.0246 (11)−0.0029 (9)−0.0017 (10)−0.0029 (9)
C130.0217 (12)0.0103 (9)0.0241 (11)0.0002 (9)−0.0016 (9)−0.0024 (8)
C140.0178 (11)0.0114 (9)0.0253 (12)0.0010 (9)−0.0014 (9)−0.0005 (8)
C150.0207 (12)0.0136 (10)0.0286 (12)−0.0022 (9)0.0003 (10)−0.0010 (9)
C160.0227 (13)0.0149 (10)0.0269 (12)0.0005 (10)0.0026 (10)0.0002 (9)
C170.0237 (13)0.0117 (10)0.0234 (11)0.0009 (9)0.0030 (10)0.0017 (8)
C180.0269 (13)0.0148 (10)0.0196 (11)0.0034 (10)−0.0006 (9)−0.0005 (8)
C190.0237 (13)0.0165 (10)0.0198 (11)0.0012 (10)−0.0018 (10)−0.0023 (9)
C200.0231 (13)0.0159 (10)0.0218 (11)0.0018 (10)−0.0005 (10)−0.0026 (9)
C210.0278 (13)0.0149 (11)0.0236 (12)0.0044 (10)0.0000 (10)0.0003 (9)
C220.0282 (14)0.0195 (11)0.0237 (12)0.0063 (10)−0.0016 (10)−0.0007 (9)
C230.0343 (15)0.0215 (12)0.0248 (12)0.0038 (11)0.0024 (11)0.0024 (10)
C240.0270 (14)0.0171 (11)0.0307 (13)0.0028 (10)−0.0005 (11)−0.0055 (9)
C250.0306 (14)0.0226 (12)0.0203 (11)0.0024 (11)−0.0016 (10)−0.0013 (9)
C260.0287 (14)0.0279 (12)0.0197 (11)0.0055 (11)−0.0058 (10)−0.0020 (10)
C270.0345 (16)0.0297 (13)0.0308 (13)−0.0056 (13)−0.0013 (12)−0.0045 (11)
Geometric parameters (Å, º) top
O1—C21.368 (3)C12—H12B0.9900
O1—C11.369 (3)C13—C141.543 (3)
O2—C91.343 (3)C13—C201.581 (3)
O2—C51.468 (3)C13—H131.0000
O3—C91.215 (3)C14—C151.531 (3)
O4—C171.441 (3)C15—C161.535 (3)
O4—C141.448 (3)C15—H15A0.9900
O5—C261.328 (3)C15—H15B0.9900
O5—C271.450 (3)C16—C211.514 (3)
O6—C261.209 (3)C16—C171.546 (3)
O7—C211.214 (3)C16—H161.0000
C1—C41.348 (3)C17—C181.528 (3)
C1—H10.9500C17—H171.0000
C2—C31.347 (4)C18—C221.533 (3)
C2—H20.9500C18—C231.540 (3)
C3—C41.430 (3)C18—C191.577 (3)
C3—H30.9500C19—C251.535 (3)
C4—C51.499 (3)C19—C201.580 (3)
C5—C61.541 (3)C19—H191.0000
C5—H51.0000C20—C211.523 (4)
C6—C101.539 (3)C20—C241.533 (3)
C6—C111.541 (3)C22—H22A0.9800
C6—C71.543 (3)C22—H22B0.9800
C7—C81.533 (3)C22—H22C0.9800
C7—C141.538 (3)C23—H23A0.9800
C7—H71.0000C23—H23B0.9800
C8—C91.495 (3)C23—H23C0.9800
C8—H8A0.9900C24—H24A0.9800
C8—H8B0.9900C24—H24B0.9800
C10—H10A0.9800C24—H24C0.9800
C10—H10B0.9800C25—C261.516 (4)
C10—H10C0.9800C25—H25A0.9900
C11—C121.525 (3)C25—H25B0.9900
C11—H11A0.9900C27—H27A0.9800
C11—H11B0.9900C27—H27B0.9800
C12—C131.526 (3)C27—H27C0.9800
C12—H12A0.9900
C2—O1—C1106.2 (2)C14—C15—C1699.77 (19)
C9—O2—C5122.25 (18)C14—C15—H15A111.8
C17—O4—C14108.00 (17)C16—C15—H15A111.8
C26—O5—C27116.02 (19)C14—C15—H15B111.8
C4—C1—O1110.8 (2)C16—C15—H15B111.8
C4—C1—H1124.6H15A—C15—H15B109.5
O1—C1—H1124.6C21—C16—C15105.23 (19)
C3—C2—O1110.3 (2)C21—C16—C17110.2 (2)
C3—C2—H2124.9C15—C16—C17102.18 (18)
O1—C2—H2124.9C21—C16—H16112.8
C2—C3—C4106.8 (2)C15—C16—H16112.8
C2—C3—H3126.6C17—C16—H16112.8
C4—C3—H3126.6O4—C17—C18110.38 (19)
C1—C4—C3105.9 (2)O4—C17—C16106.42 (18)
C1—C4—C5126.9 (2)C18—C17—C16112.89 (19)
C3—C4—C5127.3 (2)O4—C17—H17109.0
O2—C5—C4104.05 (18)C18—C17—H17109.0
O2—C5—C6113.69 (18)C16—C17—H17109.0
C4—C5—C6116.28 (18)C17—C18—C22109.56 (19)
O2—C5—H5107.5C17—C18—C23106.5 (2)
C4—C5—H5107.5C22—C18—C23108.74 (19)
C6—C5—H5107.5C17—C18—C19109.30 (18)
C10—C6—C11108.62 (18)C22—C18—C19108.3 (2)
C10—C6—C5110.7 (2)C23—C18—C19114.36 (19)
C11—C6—C5109.13 (18)C25—C19—C18109.83 (19)
C10—C6—C7110.34 (19)C25—C19—C20113.17 (19)
C11—C6—C7108.73 (19)C18—C19—C20114.12 (19)
C5—C6—C7109.28 (18)C25—C19—H19106.4
C8—C7—C14111.49 (18)C18—C19—H19106.4
C8—C7—C6108.70 (19)C20—C19—H19106.4
C14—C7—C6114.90 (19)C21—C20—C24109.4 (2)
C8—C7—H7107.1C21—C20—C19104.29 (18)
C14—C7—H7107.1C24—C20—C19113.3 (2)
C6—C7—H7107.1C21—C20—C13109.2 (2)
C9—C8—C7114.10 (19)C24—C20—C13108.09 (18)
C9—C8—H8A108.7C19—C20—C13112.45 (19)
C7—C8—H8A108.7O7—C21—C16123.2 (2)
C9—C8—H8B108.7O7—C21—C20124.5 (2)
C7—C8—H8B108.7C16—C21—C20112.2 (2)
H8A—C8—H8B107.6C18—C22—H22A109.5
O3—C9—O2117.6 (2)C18—C22—H22B109.5
O3—C9—C8122.8 (2)H22A—C22—H22B109.5
O2—C9—C8119.23 (19)C18—C22—H22C109.5
C6—C10—H10A109.5H22A—C22—H22C109.5
C6—C10—H10B109.5H22B—C22—H22C109.5
H10A—C10—H10B109.5C18—C23—H23A109.5
C6—C10—H10C109.5C18—C23—H23B109.5
H10A—C10—H10C109.5H23A—C23—H23B109.5
H10B—C10—H10C109.5C18—C23—H23C109.5
C12—C11—C6113.94 (18)H23A—C23—H23C109.5
C12—C11—H11A108.8H23B—C23—H23C109.5
C6—C11—H11A108.8C20—C24—H24A109.5
C12—C11—H11B108.8C20—C24—H24B109.5
C6—C11—H11B108.8H24A—C24—H24B109.5
H11A—C11—H11B107.7C20—C24—H24C109.5
C11—C12—C13111.8 (2)H24A—C24—H24C109.5
C11—C12—H12A109.2H24B—C24—H24C109.5
C13—C12—H12A109.2C26—C25—C19116.9 (2)
C11—C12—H12B109.2C26—C25—H25A108.1
C13—C12—H12B109.2C19—C25—H25A108.1
H12A—C12—H12B107.9C26—C25—H25B108.1
C12—C13—C14113.05 (19)C19—C25—H25B108.1
C12—C13—C20113.1 (2)H25A—C25—H25B107.3
C14—C13—C20113.16 (18)O6—C26—O5124.2 (3)
C12—C13—H13105.5O6—C26—C25124.1 (2)
C14—C13—H13105.5O5—C26—C25111.6 (2)
C20—C13—H13105.5O5—C27—H27A109.5
O4—C14—C15102.50 (17)O5—C27—H27B109.5
O4—C14—C7108.01 (18)H27A—C27—H27B109.5
C15—C14—C7113.50 (19)O5—C27—H27C109.5
O4—C14—C13110.14 (18)H27A—C27—H27C109.5
C15—C14—C13109.10 (19)H27B—C27—H27C109.5
C7—C14—C13113.05 (18)
C2—O1—C1—C4−0.5 (3)O4—C14—C15—C1645.6 (2)
C1—O1—C2—C30.7 (3)C7—C14—C15—C16161.85 (18)
O1—C2—C3—C4−0.6 (3)C13—C14—C15—C16−71.1 (2)
O1—C1—C4—C30.1 (3)C14—C15—C16—C2177.3 (2)
O1—C1—C4—C5179.1 (2)C14—C15—C16—C17−37.9 (2)
C2—C3—C4—C10.3 (3)C14—O4—C17—C18−111.5 (2)
C2—C3—C4—C5−178.7 (2)C14—O4—C17—C1611.3 (2)
C9—O2—C5—C4−159.5 (2)C21—C16—C17—O4−93.7 (2)
C9—O2—C5—C6−32.0 (3)C15—C16—C17—O417.8 (2)
C1—C4—C5—O2−146.5 (2)C21—C16—C17—C1827.6 (3)
C3—C4—C5—O232.3 (3)C15—C16—C17—C18139.03 (19)
C1—C4—C5—C687.6 (3)O4—C17—C18—C22−59.7 (2)
C3—C4—C5—C6−93.5 (3)C16—C17—C18—C22−178.62 (19)
O2—C5—C6—C10−73.1 (2)O4—C17—C18—C23−177.11 (17)
C4—C5—C6—C1047.7 (3)C16—C17—C18—C2363.9 (2)
O2—C5—C6—C11167.36 (18)O4—C17—C18—C1958.9 (2)
C4—C5—C6—C11−71.8 (2)C16—C17—C18—C19−60.1 (3)
O2—C5—C6—C748.6 (2)C17—C18—C19—C25153.7 (2)
C4—C5—C6—C7169.41 (19)C22—C18—C19—C25−87.0 (2)
C10—C6—C7—C864.1 (2)C23—C18—C19—C2534.5 (3)
C11—C6—C7—C8−176.87 (18)C17—C18—C19—C2025.4 (3)
C5—C6—C7—C8−57.9 (2)C22—C18—C19—C20144.74 (19)
C10—C6—C7—C14−170.21 (19)C23—C18—C19—C20−93.8 (2)
C11—C6—C7—C14−51.2 (2)C25—C19—C20—C21−91.2 (2)
C5—C6—C7—C1467.8 (2)C18—C19—C20—C2135.4 (2)
C14—C7—C8—C9−77.0 (2)C25—C19—C20—C2427.7 (3)
C6—C7—C8—C950.6 (2)C18—C19—C20—C24154.2 (2)
C5—O2—C9—O3−162.9 (2)C25—C19—C20—C13150.6 (2)
C5—O2—C9—C823.9 (3)C18—C19—C20—C13−82.8 (2)
C7—C8—C9—O3153.6 (2)C12—C13—C20—C21−171.48 (18)
C7—C8—C9—O2−33.5 (3)C14—C13—C20—C21−41.3 (3)
C10—C6—C11—C12175.0 (2)C12—C13—C20—C2469.6 (3)
C5—C6—C11—C12−64.2 (3)C14—C13—C20—C24−160.2 (2)
C7—C6—C11—C1254.9 (3)C12—C13—C20—C19−56.2 (2)
C6—C11—C12—C13−55.8 (3)C14—C13—C20—C1974.0 (3)
C11—C12—C13—C1450.3 (2)C15—C16—C21—O7111.6 (3)
C11—C12—C13—C20−179.43 (18)C17—C16—C21—O7−138.9 (2)
C17—O4—C14—C15−36.1 (2)C15—C16—C21—C20−69.5 (2)
C17—O4—C14—C7−156.17 (18)C17—C16—C21—C2039.9 (3)
C17—O4—C14—C1379.9 (2)C24—C20—C21—O7−14.6 (3)
C8—C7—C14—O450.7 (2)C19—C20—C21—O7106.9 (3)
C6—C7—C14—O4−73.6 (2)C13—C20—C21—O7−132.7 (2)
C8—C7—C14—C15−62.3 (2)C24—C20—C21—C16166.6 (2)
C6—C7—C14—C15173.51 (18)C19—C20—C21—C16−71.9 (2)
C8—C7—C14—C13172.8 (2)C13—C20—C21—C1648.5 (2)
C6—C7—C14—C1348.6 (3)C18—C19—C25—C26153.9 (2)
C12—C13—C14—O474.0 (2)C20—C19—C25—C26−77.3 (3)
C20—C13—C14—O4−56.2 (3)C27—O5—C26—O60.8 (4)
C12—C13—C14—C15−174.24 (18)C27—O5—C26—C25−175.0 (2)
C20—C13—C14—C1555.6 (3)C19—C25—C26—O6147.3 (3)
C12—C13—C14—C7−46.9 (3)C19—C25—C26—O5−36.9 (3)
C20—C13—C14—C7−177.13 (19)

Experimental details

Crystal data
Chemical formulaC27H34O7
Mr470.54
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)8.7174 (6), 11.7401 (8), 23.1106 (16)
V (Å3)2365.2 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.25 × 0.15 × 0.05
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		22814, 3083, 2674
Rint0.053
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.098, 1.03
No. of reflections3083
No. of parameters307
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.29, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

 

Acknowledgements

We thank the University of Malaya (PPP PS378/009B) for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
 First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationKim, J.-G., Cho, D. H. & Jang, D. O. (2004). Tetrahedron Lett. 45, 3031–3033.  Web of Science CrossRef CAS Google Scholar
 First citationKokpol, U., Chavasiri, W., Tip-Pyang, S., Veerachato, G., Zhao, F., Simpson, J. & Weavers, R. T. (1996). Phytochemistry, 41, 903–905.  CSD CrossRef CAS Web of Science Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWu, J., Zhang, S., Xiao, Q., Li, Q.-X., Huang, J.-S., Xiao, Z.-H. & Long, L.-J. (2003). Z. Naturforsch. Teil B, 58, 1216–1219.  CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o1927
https://doi.org/10.1107/S160053681002564X
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