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Acta Cryst. (2009). E65, o750    [ doi:10.1107/S1600536809008009 ]

Kokosanolide from the seed of Lansium domesticum Corr.

T. Mayanti, U. Supratman, M. R. Mukhtar, K. Awang and S. W. Ng

Abstract top

In the title compound, [systematic name: 8,14-secogammacera-7,14(27)-diene-3,21-dione], C27H32O9, each of the six-membered rings adopts the common chair conformation. In the crystal, molecules are linked by an O-H...Oester hydrogen bond into a helical chain.

Related literature top

For compounds from this plant species, see: Habaguchi et al. (1968); Kiang et al. (1967); Nishizawa et al. (1982, 1983, 1984, 1985, 1988); Saewan et al. (2006).

Experimental top

Lansium domesticum Corr. (Meliaceae) was collected in Cililin, Bandung, Indonesia, in 2006. The plant was identified by the staff at Department of Biology, Padjadjaran University. The dried and milled seeds of L.domesticum (2 kg) was extracted exhaustively by methanol at room temperature. The methanol extract (84 g) was partitioned between n-hexane and 10% aqueous methanol to give an n-hexane soluble fraction (4 g). The n-hexane extract were subjected to column chromatography on silica gel 60 by using step gradient of n-hexane and dichloromethane (8:2). The fraction eluted by n-hexane/dichloromethane (6:4) was further separated by column chromatography on silica gel (n-hexane:ethyl acetate 7:3) to give kokosanolide (48 mg).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The hydroxy H-atom was similarly treated.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C27H32O9 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
8,14-secogammacera-7,14 (27)-diene-3,21-dione top
Crystal data top
C27H32O9F(000) = 532
Mr = 500.53Dx = 1.399 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8527 reflections
a = 8.8326 (1) Åθ = 2.5–28.3°
b = 12.8977 (2) ŵ = 0.11 mm−1
c = 11.1555 (1) ÅT = 123 K
β = 110.777 (1)°Block, colorless
V = 1188.19 (3) Å30.40 × 0.30 × 0.10 mm
Z = 2
Data collection top
Bruker SMART APEX
diffractometer		2760 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
graphiteθmax = 27.5°, θmin = 2.0°
ω scansh = −11→11
11333 measured reflectionsk = −16→16
2856 independent reflectionsl = −14→14
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0619P)2 + 0.1566P]
where P = (Fo2 + 2Fc2)/3
2856 reflections(Δ/σ)max = 0.001
331 parametersΔρmax = 0.32 e Å−3
1 restraintΔρmin = −0.21 e Å−3
Crystal data top
C27H32O9V = 1188.19 (3) Å3
Mr = 500.53Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.8326 (1) ŵ = 0.11 mm−1
b = 12.8977 (2) ÅT = 123 K
c = 11.1555 (1) Å0.40 × 0.30 × 0.10 mm
β = 110.777 (1)°
Data collection top
Bruker SMART APEX
diffractometer		2760 reflections with I > 2σ(I)
11333 measured reflectionsRint = 0.020
2856 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.083Δρmax = 0.32 e Å−3
S = 1.03Δρmin = −0.21 e Å−3
2856 reflectionsAbsolute structure: ?
331 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.84140 (14)0.50022 (10)0.13328 (11)0.0178 (2)
O20.76288 (15)0.65296 (11)0.03392 (13)0.0216 (3)
O31.14818 (14)0.54506 (9)0.20719 (11)0.0149 (2)
O40.96159 (15)0.32343 (10)0.00956 (13)0.0206 (3)
O51.42245 (14)0.50619 (9)0.27176 (11)0.0153 (2)
O61.34114 (15)0.35288 (10)0.07332 (12)0.0170 (2)
H61.31350.29340.04280.026*
O71.59091 (18)0.01203 (12)0.27280 (16)0.0320 (3)
O81.77358 (16)0.12432 (10)0.38724 (14)0.0236 (3)
O92.20986 (18)0.18614 (14)0.66355 (16)0.0361 (4)
C10.6733 (2)0.47246 (17)0.10624 (19)0.0243 (4)
H1A0.66630.39890.12580.036*
H1B0.61090.48500.01540.036*
H1C0.62930.51470.15920.036*
C20.8676 (2)0.59050 (14)0.08735 (16)0.0161 (3)
C31.04435 (18)0.60764 (13)0.10460 (15)0.0146 (3)
H31.07100.68210.12760.017*
C41.09301 (19)0.58216 (13)−0.01273 (15)0.0147 (3)
H41.06740.6416−0.07430.018*
C51.27793 (19)0.57214 (13)0.05798 (16)0.0151 (3)
H51.32740.53390.00300.018*
C61.3650 (2)0.67574 (14)0.10056 (18)0.0199 (3)
H6A1.47970.66300.14980.030*
H6B1.31580.71280.15430.030*
H6C1.35510.71770.02490.030*
C71.27580 (18)0.50317 (13)0.16845 (15)0.0136 (3)
C81.22596 (19)0.39101 (13)0.12532 (16)0.0137 (3)
C91.0573 (2)0.39205 (13)0.01658 (16)0.0146 (3)
C101.0219 (2)0.47930 (13)−0.08308 (15)0.0159 (3)
C110.8397 (2)0.48559 (15)−0.16080 (16)0.0199 (3)
H11A0.80270.4195−0.20480.030*
H11B0.81930.5414−0.22420.030*
H11C0.78070.4999−0.10290.030*
C121.1023 (2)0.45050 (16)−0.18142 (17)0.0220 (4)
H12A1.05400.3864−0.22570.033*
H12B1.21870.4403−0.13670.033*
H12C1.08490.5066−0.24410.033*
C131.2208 (2)0.32682 (13)0.23880 (16)0.0161 (3)
H13A1.20150.25320.21270.019*
H13B1.12930.35060.26340.019*
C141.3790 (2)0.33558 (13)0.35547 (16)0.0162 (3)
H141.35090.31020.42970.019*
C151.4203 (2)0.45085 (13)0.38358 (15)0.0159 (3)
H151.33580.48280.41230.019*
C161.5849 (2)0.46840 (14)0.48766 (16)0.0186 (3)
H16A1.57900.44870.57170.022*
H16B1.61210.54310.49110.022*
C171.7188 (2)0.40598 (13)0.46466 (17)0.0171 (3)
H17A1.82260.41930.53550.021*
H17B1.73060.42960.38400.021*
C181.6839 (2)0.28830 (13)0.45591 (16)0.0159 (3)
C191.6878 (2)0.24514 (15)0.58587 (17)0.0204 (3)
H19A1.67740.16950.58070.031*
H19B1.59790.27460.60670.031*
H19C1.79060.26390.65290.031*
C201.5183 (2)0.26731 (13)0.35417 (16)0.0156 (3)
C211.4975 (2)0.18237 (14)0.28188 (17)0.0197 (3)
H211.39990.17460.21030.024*
C221.6205 (2)0.10045 (16)0.30943 (19)0.0225 (4)
C231.8114 (2)0.23374 (14)0.41244 (18)0.0186 (3)
H231.81070.26720.33140.022*
C241.9817 (2)0.23557 (16)0.50764 (19)0.0212 (4)
C252.0961 (2)0.31887 (18)0.53514 (19)0.0252 (4)
H252.08040.38500.49500.030*
C262.2305 (2)0.28487 (19)0.6295 (2)0.0290 (4)
H262.32640.32450.66690.035*
C272.0560 (3)0.15765 (18)0.5880 (2)0.0329 (5)
H272.00830.09230.59170.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0136 (5)0.0176 (6)0.0218 (6)0.0018 (5)0.0058 (5)0.0033 (5)
O20.0158 (6)0.0207 (6)0.0260 (6)0.0053 (5)0.0045 (5)0.0052 (5)
O30.0122 (5)0.0162 (6)0.0147 (5)0.0043 (4)0.0027 (4)0.0011 (4)
O40.0149 (6)0.0150 (6)0.0271 (6)−0.0020 (5)0.0017 (5)−0.0014 (5)
O50.0121 (5)0.0144 (5)0.0159 (5)−0.0007 (4)0.0006 (4)−0.0001 (4)
O60.0146 (5)0.0147 (5)0.0221 (6)0.0007 (5)0.0069 (5)−0.0035 (5)
O70.0263 (7)0.0196 (7)0.0467 (9)0.0014 (6)0.0086 (6)−0.0097 (6)
O80.0197 (6)0.0176 (6)0.0296 (7)0.0049 (5)0.0043 (5)−0.0040 (5)
O90.0207 (7)0.0400 (9)0.0372 (8)0.0037 (7)−0.0027 (6)0.0026 (7)
C10.0160 (8)0.0291 (10)0.0283 (9)−0.0012 (7)0.0084 (7)0.0054 (8)
C20.0154 (7)0.0169 (8)0.0152 (7)0.0018 (6)0.0045 (6)−0.0007 (6)
C30.0132 (7)0.0139 (7)0.0149 (7)0.0022 (6)0.0029 (6)0.0016 (6)
C40.0129 (7)0.0150 (7)0.0151 (7)−0.0001 (6)0.0034 (6)0.0011 (6)
C50.0123 (7)0.0147 (7)0.0169 (7)−0.0010 (6)0.0035 (6)−0.0005 (6)
C60.0170 (8)0.0151 (8)0.0243 (8)−0.0015 (6)0.0033 (6)0.0028 (6)
C70.0101 (7)0.0139 (7)0.0149 (7)0.0008 (6)0.0021 (6)−0.0012 (6)
C80.0104 (7)0.0126 (7)0.0165 (7)−0.0005 (6)0.0027 (6)−0.0014 (6)
C90.0130 (7)0.0141 (7)0.0158 (7)0.0017 (6)0.0041 (6)−0.0031 (6)
C100.0146 (7)0.0174 (8)0.0138 (7)0.0004 (6)0.0027 (6)−0.0015 (6)
C110.0150 (8)0.0229 (8)0.0171 (7)0.0009 (7)0.0001 (6)−0.0012 (7)
C120.0219 (8)0.0274 (9)0.0169 (7)0.0014 (7)0.0072 (7)−0.0029 (7)
C130.0131 (7)0.0140 (7)0.0189 (8)−0.0006 (6)0.0029 (6)0.0022 (6)
C140.0146 (7)0.0155 (7)0.0159 (7)0.0014 (6)0.0023 (6)0.0011 (6)
C150.0158 (7)0.0154 (7)0.0140 (7)0.0042 (6)0.0021 (6)0.0002 (6)
C160.0185 (8)0.0156 (8)0.0168 (7)0.0032 (6)0.0001 (6)−0.0027 (6)
C170.0153 (7)0.0158 (8)0.0169 (7)0.0008 (6)0.0016 (6)−0.0001 (6)
C180.0137 (7)0.0160 (8)0.0163 (7)0.0023 (6)0.0033 (6)0.0001 (6)
C190.0206 (8)0.0220 (9)0.0160 (8)0.0033 (7)0.0034 (6)0.0046 (7)
C200.0140 (7)0.0157 (7)0.0162 (7)0.0017 (6)0.0043 (6)0.0029 (6)
C210.0163 (8)0.0187 (8)0.0213 (8)0.0025 (7)0.0032 (6)−0.0001 (7)
C220.0203 (8)0.0199 (8)0.0267 (9)0.0034 (7)0.0076 (7)−0.0028 (7)
C230.0159 (8)0.0173 (8)0.0214 (8)0.0026 (6)0.0051 (7)−0.0020 (7)
C240.0169 (8)0.0244 (9)0.0217 (8)0.0025 (7)0.0059 (7)−0.0038 (7)
C250.0183 (8)0.0317 (10)0.0274 (9)−0.0014 (8)0.0104 (7)−0.0025 (8)
C260.0176 (9)0.0388 (12)0.0300 (10)−0.0009 (8)0.0075 (8)−0.0078 (9)
C270.0204 (9)0.0289 (10)0.0392 (11)0.0034 (8)−0.0022 (8)0.0025 (9)
Geometric parameters (Å, °) top
O1—C21.325 (2)C11—H11B0.9800
O1—C11.451 (2)C11—H11C0.9800
O2—C21.212 (2)C12—H12A0.9800
O3—C31.4344 (19)C12—H12B0.9800
O3—C71.4473 (19)C12—H12C0.9800
O4—C91.207 (2)C13—C141.539 (2)
O5—C71.3959 (18)C13—H13A0.9900
O5—C151.443 (2)C13—H13B0.9900
O6—C81.4255 (19)C14—C201.517 (2)
O6—H60.8400C14—C151.536 (2)
O7—C221.208 (3)C14—H141.0000
O8—C221.358 (2)C15—C161.521 (2)
O8—C231.455 (2)C15—H151.0000
O9—C261.360 (3)C16—C171.526 (2)
O9—C271.370 (2)C16—H16A0.9900
C1—H1A0.9800C16—H16B0.9900
C1—H1B0.9800C17—C181.545 (2)
C1—H1C0.9800C17—H17A0.9900
C2—C31.520 (2)C17—H17B0.9900
C3—C41.551 (2)C18—C201.524 (2)
C3—H31.0000C18—C231.545 (2)
C4—C51.547 (2)C18—C191.542 (2)
C4—C101.556 (2)C19—H19A0.9800
C4—H41.0000C19—H19B0.9800
C5—C71.525 (2)C19—H19C0.9800
C5—C61.531 (2)C20—C211.334 (2)
C5—H51.0000C21—C221.468 (2)
C6—H6A0.9800C21—H210.9500
C6—H6B0.9800C23—C241.503 (2)
C6—H6C0.9800C23—H231.0000
C7—C81.539 (2)C24—C271.352 (3)
C8—C131.527 (2)C24—C251.431 (3)
C8—C91.552 (2)C25—C261.350 (3)
C9—C101.534 (2)C25—H250.9500
C10—C111.536 (2)C26—H260.9500
C10—C121.548 (2)C27—H270.9500
C11—H11A0.9800
C2—O1—C1116.25 (14)H12B—C12—H12C109.5
C3—O3—C7108.49 (12)C8—C13—C14112.08 (13)
C7—O5—C15114.02 (12)C8—C13—H13A109.2
C8—O6—H6109.5C14—C13—H13A109.2
C22—O8—C23116.86 (14)C8—C13—H13B109.2
C26—O9—C27106.34 (17)C14—C13—H13B109.2
O1—C1—H1A109.5H13A—C13—H13B107.9
O1—C1—H1B109.5C20—C14—C15115.40 (14)
H1A—C1—H1B109.5C20—C14—C13116.45 (14)
O1—C1—H1C109.5C15—C14—C13108.80 (13)
H1A—C1—H1C109.5C20—C14—H14105.0
H1B—C1—H1C109.5C15—C14—H14105.0
O2—C2—O1124.55 (16)C13—C14—H14105.0
O2—C2—C3122.41 (16)O5—C15—C16106.52 (14)
O1—C2—C3113.02 (14)O5—C15—C14112.16 (13)
O3—C3—C2110.89 (13)C16—C15—C14113.15 (13)
O3—C3—C4105.31 (12)O5—C15—H15108.3
C2—C3—C4116.24 (13)C16—C15—H15108.3
O3—C3—H3108.0C14—C15—H15108.3
C2—C3—H3108.0C15—C16—C17112.39 (14)
C4—C3—H3108.0C15—C16—H16A109.1
C5—C4—C398.39 (12)C17—C16—H16A109.1
C5—C4—C10110.50 (13)C15—C16—H16B109.1
C3—C4—C10115.04 (14)C17—C16—H16B109.1
C5—C4—H4110.8H16A—C16—H16B107.9
C3—C4—H4110.8C16—C17—C18112.30 (15)
C10—C4—H4110.8C16—C17—H17A109.1
C7—C5—C6114.03 (14)C18—C17—H17A109.1
C7—C5—C498.47 (13)C16—C17—H17B109.1
C6—C5—C4114.11 (14)C18—C17—H17B109.1
C7—C5—H5109.9H17A—C17—H17B107.9
C6—C5—H5109.9C20—C18—C23107.41 (13)
C4—C5—H5109.9C20—C18—C19109.36 (14)
C5—C6—H6A109.5C23—C18—C19110.80 (14)
C5—C6—H6B109.5C20—C18—C17109.81 (14)
H6A—C6—H6B109.5C23—C18—C17108.41 (14)
C5—C6—H6C109.5C19—C18—C17110.97 (15)
H6A—C6—H6C109.5C18—C19—H19A109.5
H6B—C6—H6C109.5C18—C19—H19B109.5
O5—C7—O3109.63 (12)H19A—C19—H19B109.5
O5—C7—C5112.14 (13)C18—C19—H19C109.5
O3—C7—C5104.93 (13)H19A—C19—H19C109.5
O5—C7—C8111.30 (13)H19B—C19—H19C109.5
O3—C7—C8106.12 (12)C21—C20—C14122.97 (16)
C5—C7—C8112.32 (13)C21—C20—C18119.08 (15)
O6—C8—C13112.70 (13)C14—C20—C18117.20 (14)
O6—C8—C7106.58 (12)C20—C21—C22122.12 (16)
C13—C8—C7109.87 (13)C20—C21—H21118.9
O6—C8—C9108.09 (13)C22—C21—H21118.9
C13—C8—C9110.49 (13)O7—C22—O8118.50 (17)
C7—C8—C9108.97 (13)O7—C22—C21123.59 (18)
O4—C9—C10122.19 (15)O8—C22—C21117.77 (17)
O4—C9—C8120.02 (15)O8—C23—C24104.80 (14)
C10—C9—C8117.72 (14)O8—C23—C18111.08 (14)
C9—C10—C11110.56 (14)C24—C23—C18115.43 (15)
C9—C10—C12108.10 (14)O8—C23—H23108.4
C11—C10—C12105.35 (13)C24—C23—H23108.4
C9—C10—C4108.54 (13)C18—C23—H23108.4
C11—C10—C4113.22 (14)C27—C24—C25106.02 (18)
C12—C10—C4110.95 (14)C27—C24—C23125.89 (18)
C10—C11—H11A109.5C25—C24—C23128.07 (18)
C10—C11—H11B109.5C26—C25—C24106.4 (2)
H11A—C11—H11B109.5C26—C25—H25126.8
C10—C11—H11C109.5C24—C25—H25126.8
H11A—C11—H11C109.5C25—C26—O9110.73 (19)
H11B—C11—H11C109.5C25—C26—H26124.6
C10—C12—H12A109.5O9—C26—H26124.6
C10—C12—H12B109.5C24—C27—O9110.5 (2)
H12A—C12—H12B109.5C24—C27—H27124.7
C10—C12—H12C109.5O9—C27—H27124.7
H12A—C12—H12C109.5
C1—O1—C2—O25.7 (2)C3—C4—C10—C12−169.29 (14)
C1—O1—C2—C3−172.55 (15)O6—C8—C13—C1466.52 (17)
C7—O3—C3—C2138.99 (13)C7—C8—C13—C14−52.18 (17)
C7—O3—C3—C412.48 (16)C9—C8—C13—C14−172.45 (13)
O2—C2—C3—O3158.88 (15)C8—C13—C14—C20−81.44 (18)
O1—C2—C3—O3−22.83 (19)C8—C13—C14—C1551.05 (18)
O2—C2—C3—C4−80.9 (2)C7—O5—C15—C16−176.46 (13)
O1—C2—C3—C497.37 (17)C7—O5—C15—C1459.23 (17)
O3—C3—C4—C5−37.89 (15)C20—C14—C15—O580.22 (17)
C2—C3—C4—C5−161.05 (14)C13—C14—C15—O5−52.82 (17)
O3—C3—C4—C1079.47 (16)C20—C14—C15—C16−40.3 (2)
C2—C3—C4—C10−43.69 (19)C13—C14—C15—C16−173.35 (13)
C3—C4—C5—C747.08 (14)O5—C15—C16—C17−74.21 (17)
C10—C4—C5—C7−73.71 (15)C14—C15—C16—C1749.5 (2)
C3—C4—C5—C6−74.10 (17)C15—C16—C17—C18−57.93 (19)
C10—C4—C5—C6165.11 (15)C16—C17—C18—C2054.44 (19)
C15—O5—C7—O357.64 (17)C16—C17—C18—C23171.52 (13)
C15—O5—C7—C5173.77 (13)C16—C17—C18—C19−66.58 (18)
C15—O5—C7—C8−59.45 (16)C15—C14—C20—C21−150.03 (16)
C3—O3—C7—O5139.56 (13)C13—C14—C20—C21−20.6 (2)
C3—O3—C7—C518.95 (16)C15—C14—C20—C1840.0 (2)
C3—O3—C7—C8−100.14 (14)C13—C14—C20—C18169.39 (14)
C6—C5—C7—O5−39.71 (19)C23—C18—C20—C2125.9 (2)
C4—C5—C7—O5−160.94 (13)C19—C18—C20—C21−94.40 (19)
C6—C5—C7—O379.23 (16)C17—C18—C20—C21143.61 (17)
C4—C5—C7—O3−42.00 (15)C23—C18—C20—C14−163.70 (15)
C6—C5—C7—C8−165.93 (13)C19—C18—C20—C1475.99 (18)
C4—C5—C7—C872.83 (15)C17—C18—C20—C14−46.00 (19)
O5—C7—C8—O6−67.25 (16)C14—C20—C21—C22−160.32 (17)
O3—C7—C8—O6173.53 (12)C18—C20—C21—C229.5 (3)
C5—C7—C8—O659.42 (16)C23—O8—C22—O7170.30 (18)
O5—C7—C8—C1355.14 (17)C23—O8—C22—C21−13.9 (2)
O3—C7—C8—C13−64.08 (15)C20—C21—C22—O7157.6 (2)
C5—C7—C8—C13−178.18 (13)C20—C21—C22—O8−18.0 (3)
O5—C7—C8—C9176.32 (12)C22—O8—C23—C24175.76 (15)
O3—C7—C8—C957.11 (15)C22—O8—C23—C1850.5 (2)
C5—C7—C8—C9−57.00 (17)C20—C18—C23—O8−54.44 (18)
O6—C8—C9—O4100.48 (17)C19—C18—C23—O864.95 (18)
C13—C8—C9—O4−23.3 (2)C17—C18—C23—O8−173.05 (14)
C7—C8—C9—O4−144.06 (15)C20—C18—C23—C24−173.55 (15)
O6—C8—C9—C10−76.61 (17)C19—C18—C23—C24−54.2 (2)
C13—C8—C9—C10159.65 (14)C17—C18—C23—C2467.85 (19)
C7—C8—C9—C1038.84 (18)O8—C23—C24—C27−23.5 (3)
O4—C9—C10—C1117.8 (2)C18—C23—C24—C2799.1 (2)
C8—C9—C10—C11−165.21 (13)O8—C23—C24—C25158.54 (18)
O4—C9—C10—C12−97.08 (19)C18—C23—C24—C25−78.9 (2)
C8—C9—C10—C1279.95 (17)C27—C24—C25—C260.2 (2)
O4—C9—C10—C4142.50 (16)C23—C24—C25—C26178.52 (18)
C8—C9—C10—C4−40.47 (19)C24—C25—C26—O90.1 (2)
C5—C4—C10—C959.63 (17)C27—O9—C26—C25−0.4 (2)
C3—C4—C10—C9−50.65 (17)C25—C24—C27—O9−0.4 (2)
C5—C4—C10—C11−177.22 (14)C23—C24—C27—O9−178.81 (18)
C3—C4—C10—C1172.50 (17)C26—O9—C27—C240.5 (2)
C5—C4—C10—C12−59.01 (17)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O2i0.842.012.854 (2)178
Symmetry codes: (i) −x+2, y−1/2, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O2i0.842.012.854 (2)178
Symmetry codes: (i) −x+2, y−1/2, −z.
Acknowledgements top

This work was supported by the Directorate of Higher Education, Indonesia, University of Padjadjaran (I-MHERE Project) and the Sciencefund (12–02–03–2063).

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Habaguchi, K., Watanabe, M., Nakadaira, Y., Nakanishi, K., Kiang, A. K. & Lim, F. L. (1968). Tetrahedron Lett. Volume? 3731–3734.

Kiang, A. K., Tan, E. L., Lim, F. Y., Habaguchi, K., Nakanishi, K., Fachan, L. & Ourisson, G. (1967). Tetrahedron Lett. 37, 3571–3574.

Nishizawa, M., Nademoto, Y., Sastrapradja, S., Shiro, M. & Hayashi, Y. (1985). J. Org. Chem. 50, 5487–5490.

Nishizawa, M., Nademoto, Y., Sastrapradja, S., Shiro, M. & Hayashi, Y. (1988). Phytochemistry, 27, 237–239.

Nishizawa, M., Nishide, H. & Hayashi, Y. (1984). Tetrahedron Lett. 25, 5071–5074.

Nishizawa, M., Nishide, H., Hayashi, Y. & Kosela, S. (1982). Tetrahedron Lett. 23, 1349–1350.

Nishizawa, M., Nishide, H., Kosela, S. & Hayashi, Y. (1983). J. Org. Chem. 48, 4462–4466.

Saewan, N., Sutherland, J. D. & Chantrapromma, K. (2006). Phytochemistry, 67, 2288–2293.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.