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Kokosanolide from the seed of Lansium domesticum Corr.

aDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Padjadjaran University, Jatinangor 45363, Indonesia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 4 March 2009; accepted 4 March 2009; online 14 March 2009)

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

For compounds from this plant species, see: Habaguchi et al. (1968[Habaguchi, K., Watanabe, M., Nakadaira, Y., Nakanishi, K., Kiang, A. K. & Lim, F. L. (1968). Tetrahedron Lett. 9, 3731-3734.]); Kiang et al. (1967[Kiang, A. K., Tan, E. L., Lim, F. Y., Habaguchi, K., Nakanishi, K., Fachan, L. & Ourisson, G. (1967). Tetrahedron Lett. 37, 3571-3574.]); Nishizawa et al. (1982[Nishizawa, M., Nishide, H., Hayashi, Y. & Kosela, S. (1982). Tetrahedron Lett. 23, 1349-1350.], 1983[Nishizawa, M., Nishide, H., Kosela, S. & Hayashi, Y. (1983). J. Org. Chem. 48, 4462-4466.], 1984[Nishizawa, M., Nishide, H. & Hayashi, Y. (1984). Tetrahedron Lett. 25, 5071-5074.], 1985[Nishizawa, M., Nademoto, Y., Sastrapradja, S., Shiro, M. & Hayashi, Y. (1985). J. Org. Chem. 50, 5487-5490.], 1988[Nishizawa, M., Nademoto, Y., Sastrapradja, S., Shiro, M. & Hayashi, Y. (1988). Phytochemistry, 27, 237-239.]); Saewan et al. (2006[Saewan, N., Sutherland, J. D. & Chantrapromma, K. (2006). Phytochemistry, 67, 2288-2293.]).

[Scheme 1]

Experimental

Crystal data
  • C27H32O9

  • Mr = 500.53

  • Monoclinic, P 21

  • a = 8.8326 (1) Å

  • b = 12.8977 (2) Å

  • c = 11.1555 (1) Å

  • β = 110.777 (1)°

  • V = 1188.19 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 123 K

  • 0.40 × 0.30 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 11333 measured reflections

  • 2856 independent reflections

  • 2760 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.083

  • S = 1.03

  • 2856 reflections

  • 331 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O6—H6⋯O2i 0.84 2.01 2.854 (2) 178
Symmetry code: (i) [-x+2, y-{\script{1\over 2}}, -z].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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 m3
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 mm1
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
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
ω scansh = 1111
11333 measured reflectionsk = 1616
2856 independent reflectionsl = 1414
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 Å3
1 restraintΔρmin = 0.21 e Å3
Crystal data top
C27H32O9V = 1188.19 (3) Å3
Mr = 500.53Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.8326 (1) ŵ = 0.11 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0301 restraint
wR(F2) = 0.083H-atom parameters constrained
S = 1.03Δρmax = 0.32 e Å3
2856 reflectionsΔρmin = 0.21 e Å3
331 parameters
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)
H41.06740.64160.07430.018*
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)
H11A0.80270.41950.20480.030*
H11B0.81930.54140.22420.030*
H11C0.78070.49990.10290.030*
C121.1023 (2)0.45050 (16)0.18142 (17)0.0220 (4)
H12A1.05400.38640.22570.033*
H12B1.21870.44030.13670.033*
H12C1.08490.50660.24410.033*
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, º) 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—C12169.29 (14)
C1—O1—C2—C3172.55 (15)O6—C8—C13—C1466.52 (17)
C7—O3—C3—C2138.99 (13)C7—C8—C13—C1452.18 (17)
C7—O3—C3—C412.48 (16)C9—C8—C13—C14172.45 (13)
O2—C2—C3—O3158.88 (15)C8—C13—C14—C2081.44 (18)
O1—C2—C3—O322.83 (19)C8—C13—C14—C1551.05 (18)
O2—C2—C3—C480.9 (2)C7—O5—C15—C16176.46 (13)
O1—C2—C3—C497.37 (17)C7—O5—C15—C1459.23 (17)
O3—C3—C4—C537.89 (15)C20—C14—C15—O580.22 (17)
C2—C3—C4—C5161.05 (14)C13—C14—C15—O552.82 (17)
O3—C3—C4—C1079.47 (16)C20—C14—C15—C1640.3 (2)
C2—C3—C4—C1043.69 (19)C13—C14—C15—C16173.35 (13)
C3—C4—C5—C747.08 (14)O5—C15—C16—C1774.21 (17)
C10—C4—C5—C773.71 (15)C14—C15—C16—C1749.5 (2)
C3—C4—C5—C674.10 (17)C15—C16—C17—C1857.93 (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—C1966.58 (18)
C15—O5—C7—C859.45 (16)C15—C14—C20—C21150.03 (16)
C3—O3—C7—O5139.56 (13)C13—C14—C20—C2120.6 (2)
C3—O3—C7—C518.95 (16)C15—C14—C20—C1840.0 (2)
C3—O3—C7—C8100.14 (14)C13—C14—C20—C18169.39 (14)
C6—C5—C7—O539.71 (19)C23—C18—C20—C2125.9 (2)
C4—C5—C7—O5160.94 (13)C19—C18—C20—C2194.40 (19)
C6—C5—C7—O379.23 (16)C17—C18—C20—C21143.61 (17)
C4—C5—C7—O342.00 (15)C23—C18—C20—C14163.70 (15)
C6—C5—C7—C8165.93 (13)C19—C18—C20—C1475.99 (18)
C4—C5—C7—C872.83 (15)C17—C18—C20—C1446.00 (19)
O5—C7—C8—O667.25 (16)C14—C20—C21—C22160.32 (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—C2113.9 (2)
O3—C7—C8—C1364.08 (15)C20—C21—C22—O7157.6 (2)
C5—C7—C8—C13178.18 (13)C20—C21—C22—O818.0 (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—C957.00 (17)C20—C18—C23—O854.44 (18)
O6—C8—C9—O4100.48 (17)C19—C18—C23—O864.95 (18)
C13—C8—C9—O423.3 (2)C17—C18—C23—O8173.05 (14)
C7—C8—C9—O4144.06 (15)C20—C18—C23—C24173.55 (15)
O6—C8—C9—C1076.61 (17)C19—C18—C23—C2454.2 (2)
C13—C8—C9—C10159.65 (14)C17—C18—C23—C2467.85 (19)
C7—C8—C9—C1038.84 (18)O8—C23—C24—C2723.5 (3)
O4—C9—C10—C1117.8 (2)C18—C23—C24—C2799.1 (2)
C8—C9—C10—C11165.21 (13)O8—C23—C24—C25158.54 (18)
O4—C9—C10—C1297.08 (19)C18—C23—C24—C2578.9 (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—C440.47 (19)C24—C25—C26—O90.1 (2)
C5—C4—C10—C959.63 (17)C27—O9—C26—C250.4 (2)
C3—C4—C10—C950.65 (17)C25—C24—C27—O90.4 (2)
C5—C4—C10—C11177.22 (14)C23—C24—C27—O9178.81 (18)
C3—C4—C10—C1172.50 (17)C26—O9—C27—C240.5 (2)
C5—C4—C10—C1259.01 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O2i0.842.012.854 (2)178
Symmetry code: (i) x+2, y1/2, z.

Experimental details

Crystal data
Chemical formulaC27H32O9
Mr500.53
Crystal system, space groupMonoclinic, P21
Temperature (K)123
a, b, c (Å)8.8326 (1), 12.8977 (2), 11.1555 (1)
β (°) 110.777 (1)
V3)1188.19 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.40 × 0.30 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11333, 2856, 2760
Rint0.020
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.083, 1.03
No. of reflections2856
No. of parameters331
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O2i0.842.012.854 (2)178
Symmetry code: (i) x+2, y1/2, z.
 

Acknowledgements

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

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