Kokosanolide from the seed of Lansium domesticum Corr.

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

doi:10.1107/S1600536809008009

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o750

doi:10.1107/S1600536809008009

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Kokosanolide from the seed of Lansium domesticum Corr.

Tri Mayanti,^a Unang Supratman,^a Mat Ropi Mukhtar,^b Khalijah Awang ^b and Seik Weng Ng ^b ^*

^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⋯O_ester hydrogen bond into a helical chain.

Related literature

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

Crystal data

C₂₇H₃₂O₉
M_r = 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)
R_int = 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
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008009/bt2893sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008009/bt2893Isup2.hkl

checkCIF report

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).

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

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

C₂₇H₃₂O₉	F(000) = 532
M_r = 500.53	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8527 reflections
a = 8.8326 (1) Å	θ = 2.5–28.3°
b = 12.8977 (2) Å	µ = 0.11 mm⁻¹
c = 11.1555 (1) Å	T = 123 K
β = 110.777 (1)°	Block, colorless
V = 1188.19 (3) Å³	0.40 × 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 tube	R_int = 0.020
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
ω scans	h = −11→11
11333 measured reflections	k = −16→16
2856 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0619P)² + 0.1566P] where P = (F_o² + 2F_c²)/3
2856 reflections	(Δ/σ)_max = 0.001
331 parameters	Δρ_max = 0.32 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₇H₃₂O₉	V = 1188.19 (3) Å³
M_r = 500.53	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.8326 (1) Å	µ = 0.11 mm⁻¹
b = 12.8977 (2) Å	T = 123 K
c = 11.1555 (1) Å	0.40 × 0.30 × 0.10 mm
β = 110.777 (1)°

Data collection top

Bruker SMART APEX diffractometer	2760 reflections with I > 2σ(I)
11333 measured reflections	R_int = 0.020
2856 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	1 restraint
wR(F²) = 0.083	H-atom parameters constrained
S = 1.03	Δρ_max = 0.32 e Å⁻³
2856 reflections	Δρ_min = −0.21 e Å⁻³
331 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.84140 (14)	0.50022 (10)	0.13328 (11)	0.0178 (2)
O2	0.76288 (15)	0.65296 (11)	0.03392 (13)	0.0216 (3)
O3	1.14818 (14)	0.54506 (9)	0.20719 (11)	0.0149 (2)
O4	0.96159 (15)	0.32343 (10)	0.00956 (13)	0.0206 (3)
O5	1.42245 (14)	0.50619 (9)	0.27176 (11)	0.0153 (2)
O6	1.34114 (15)	0.35288 (10)	0.07332 (12)	0.0170 (2)
H6	1.3135	0.2934	0.0428	0.026*
O7	1.59091 (18)	0.01203 (12)	0.27280 (16)	0.0320 (3)
O8	1.77358 (16)	0.12432 (10)	0.38724 (14)	0.0236 (3)
O9	2.20986 (18)	0.18614 (14)	0.66355 (16)	0.0361 (4)
C1	0.6733 (2)	0.47246 (17)	0.10624 (19)	0.0243 (4)
H1A	0.6663	0.3989	0.1258	0.036*
H1B	0.6109	0.4850	0.0154	0.036*
H1C	0.6293	0.5147	0.1592	0.036*
C2	0.8676 (2)	0.59050 (14)	0.08735 (16)	0.0161 (3)
C3	1.04435 (18)	0.60764 (13)	0.10460 (15)	0.0146 (3)
H3	1.0710	0.6821	0.1276	0.017*
C4	1.09301 (19)	0.58216 (13)	−0.01273 (15)	0.0147 (3)
H4	1.0674	0.6416	−0.0743	0.018*
C5	1.27793 (19)	0.57214 (13)	0.05798 (16)	0.0151 (3)
H5	1.3274	0.5339	0.0030	0.018*
C6	1.3650 (2)	0.67574 (14)	0.10056 (18)	0.0199 (3)
H6A	1.4797	0.6630	0.1498	0.030*
H6B	1.3158	0.7128	0.1543	0.030*
H6C	1.3551	0.7177	0.0249	0.030*
C7	1.27580 (18)	0.50317 (13)	0.16845 (15)	0.0136 (3)
C8	1.22596 (19)	0.39101 (13)	0.12532 (16)	0.0137 (3)
C9	1.0573 (2)	0.39205 (13)	0.01658 (16)	0.0146 (3)
C10	1.0219 (2)	0.47930 (13)	−0.08308 (15)	0.0159 (3)
C11	0.8397 (2)	0.48559 (15)	−0.16080 (16)	0.0199 (3)
H11A	0.8027	0.4195	−0.2048	0.030*
H11B	0.8193	0.5414	−0.2242	0.030*
H11C	0.7807	0.4999	−0.1029	0.030*
C12	1.1023 (2)	0.45050 (16)	−0.18142 (17)	0.0220 (4)
H12A	1.0540	0.3864	−0.2257	0.033*
H12B	1.2187	0.4403	−0.1367	0.033*
H12C	1.0849	0.5066	−0.2441	0.033*
C13	1.2208 (2)	0.32682 (13)	0.23880 (16)	0.0161 (3)
H13A	1.2015	0.2532	0.2127	0.019*
H13B	1.1293	0.3506	0.2634	0.019*
C14	1.3790 (2)	0.33558 (13)	0.35547 (16)	0.0162 (3)
H14	1.3509	0.3102	0.4297	0.019*
C15	1.4203 (2)	0.45085 (13)	0.38358 (15)	0.0159 (3)
H15	1.3358	0.4828	0.4123	0.019*
C16	1.5849 (2)	0.46840 (14)	0.48766 (16)	0.0186 (3)
H16A	1.5790	0.4487	0.5717	0.022*
H16B	1.6121	0.5431	0.4911	0.022*
C17	1.7188 (2)	0.40598 (13)	0.46466 (17)	0.0171 (3)
H17A	1.8226	0.4193	0.5355	0.021*
H17B	1.7306	0.4296	0.3840	0.021*
C18	1.6839 (2)	0.28830 (13)	0.45591 (16)	0.0159 (3)
C19	1.6878 (2)	0.24514 (15)	0.58587 (17)	0.0204 (3)
H19A	1.6774	0.1695	0.5807	0.031*
H19B	1.5979	0.2746	0.6067	0.031*
H19C	1.7906	0.2639	0.6529	0.031*
C20	1.5183 (2)	0.26731 (13)	0.35417 (16)	0.0156 (3)
C21	1.4975 (2)	0.18237 (14)	0.28188 (17)	0.0197 (3)
H21	1.3999	0.1746	0.2103	0.024*
C22	1.6205 (2)	0.10045 (16)	0.30943 (19)	0.0225 (4)
C23	1.8114 (2)	0.23374 (14)	0.41244 (18)	0.0186 (3)
H23	1.8107	0.2672	0.3314	0.022*
C24	1.9817 (2)	0.23557 (16)	0.50764 (19)	0.0212 (4)
C25	2.0961 (2)	0.31887 (18)	0.53514 (19)	0.0252 (4)
H25	2.0804	0.3850	0.4950	0.030*
C26	2.2305 (2)	0.28487 (19)	0.6295 (2)	0.0290 (4)
H26	2.3264	0.3245	0.6669	0.035*
C27	2.0560 (3)	0.15765 (18)	0.5880 (2)	0.0329 (5)
H27	2.0083	0.0923	0.5917	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0136 (5)	0.0176 (6)	0.0218 (6)	0.0018 (5)	0.0058 (5)	0.0033 (5)
O2	0.0158 (6)	0.0207 (6)	0.0260 (6)	0.0053 (5)	0.0045 (5)	0.0052 (5)
O3	0.0122 (5)	0.0162 (6)	0.0147 (5)	0.0043 (4)	0.0027 (4)	0.0011 (4)
O4	0.0149 (6)	0.0150 (6)	0.0271 (6)	−0.0020 (5)	0.0017 (5)	−0.0014 (5)
O5	0.0121 (5)	0.0144 (5)	0.0159 (5)	−0.0007 (4)	0.0006 (4)	−0.0001 (4)
O6	0.0146 (5)	0.0147 (5)	0.0221 (6)	0.0007 (5)	0.0069 (5)	−0.0035 (5)
O7	0.0263 (7)	0.0196 (7)	0.0467 (9)	0.0014 (6)	0.0086 (6)	−0.0097 (6)
O8	0.0197 (6)	0.0176 (6)	0.0296 (7)	0.0049 (5)	0.0043 (5)	−0.0040 (5)
O9	0.0207 (7)	0.0400 (9)	0.0372 (8)	0.0037 (7)	−0.0027 (6)	0.0026 (7)
C1	0.0160 (8)	0.0291 (10)	0.0283 (9)	−0.0012 (7)	0.0084 (7)	0.0054 (8)
C2	0.0154 (7)	0.0169 (8)	0.0152 (7)	0.0018 (6)	0.0045 (6)	−0.0007 (6)
C3	0.0132 (7)	0.0139 (7)	0.0149 (7)	0.0022 (6)	0.0029 (6)	0.0016 (6)
C4	0.0129 (7)	0.0150 (7)	0.0151 (7)	−0.0001 (6)	0.0034 (6)	0.0011 (6)
C5	0.0123 (7)	0.0147 (7)	0.0169 (7)	−0.0010 (6)	0.0035 (6)	−0.0005 (6)
C6	0.0170 (8)	0.0151 (8)	0.0243 (8)	−0.0015 (6)	0.0033 (6)	0.0028 (6)
C7	0.0101 (7)	0.0139 (7)	0.0149 (7)	0.0008 (6)	0.0021 (6)	−0.0012 (6)
C8	0.0104 (7)	0.0126 (7)	0.0165 (7)	−0.0005 (6)	0.0027 (6)	−0.0014 (6)
C9	0.0130 (7)	0.0141 (7)	0.0158 (7)	0.0017 (6)	0.0041 (6)	−0.0031 (6)
C10	0.0146 (7)	0.0174 (8)	0.0138 (7)	0.0004 (6)	0.0027 (6)	−0.0015 (6)
C11	0.0150 (8)	0.0229 (8)	0.0171 (7)	0.0009 (7)	0.0001 (6)	−0.0012 (7)
C12	0.0219 (8)	0.0274 (9)	0.0169 (7)	0.0014 (7)	0.0072 (7)	−0.0029 (7)
C13	0.0131 (7)	0.0140 (7)	0.0189 (8)	−0.0006 (6)	0.0029 (6)	0.0022 (6)
C14	0.0146 (7)	0.0155 (7)	0.0159 (7)	0.0014 (6)	0.0023 (6)	0.0011 (6)
C15	0.0158 (7)	0.0154 (7)	0.0140 (7)	0.0042 (6)	0.0021 (6)	0.0002 (6)
C16	0.0185 (8)	0.0156 (8)	0.0168 (7)	0.0032 (6)	0.0001 (6)	−0.0027 (6)
C17	0.0153 (7)	0.0158 (8)	0.0169 (7)	0.0008 (6)	0.0016 (6)	−0.0001 (6)
C18	0.0137 (7)	0.0160 (8)	0.0163 (7)	0.0023 (6)	0.0033 (6)	0.0001 (6)
C19	0.0206 (8)	0.0220 (9)	0.0160 (8)	0.0033 (7)	0.0034 (6)	0.0046 (7)
C20	0.0140 (7)	0.0157 (7)	0.0162 (7)	0.0017 (6)	0.0043 (6)	0.0029 (6)
C21	0.0163 (8)	0.0187 (8)	0.0213 (8)	0.0025 (7)	0.0032 (6)	−0.0001 (7)
C22	0.0203 (8)	0.0199 (8)	0.0267 (9)	0.0034 (7)	0.0076 (7)	−0.0028 (7)
C23	0.0159 (8)	0.0173 (8)	0.0214 (8)	0.0026 (6)	0.0051 (7)	−0.0020 (7)
C24	0.0169 (8)	0.0244 (9)	0.0217 (8)	0.0025 (7)	0.0059 (7)	−0.0038 (7)
C25	0.0183 (8)	0.0317 (10)	0.0274 (9)	−0.0014 (8)	0.0104 (7)	−0.0025 (8)
C26	0.0176 (9)	0.0388 (12)	0.0300 (10)	−0.0009 (8)	0.0075 (8)	−0.0078 (9)
C27	0.0204 (9)	0.0289 (10)	0.0392 (11)	0.0034 (8)	−0.0022 (8)	0.0025 (9)

Geometric parameters (Å, º) top

O1—C2	1.325 (2)	C11—H11B	0.9800
O1—C1	1.451 (2)	C11—H11C	0.9800
O2—C2	1.212 (2)	C12—H12A	0.9800
O3—C3	1.4344 (19)	C12—H12B	0.9800
O3—C7	1.4473 (19)	C12—H12C	0.9800
O4—C9	1.207 (2)	C13—C14	1.539 (2)
O5—C7	1.3959 (18)	C13—H13A	0.9900
O5—C15	1.443 (2)	C13—H13B	0.9900
O6—C8	1.4255 (19)	C14—C20	1.517 (2)
O6—H6	0.8400	C14—C15	1.536 (2)
O7—C22	1.208 (3)	C14—H14	1.0000
O8—C22	1.358 (2)	C15—C16	1.521 (2)
O8—C23	1.455 (2)	C15—H15	1.0000
O9—C26	1.360 (3)	C16—C17	1.526 (2)
O9—C27	1.370 (2)	C16—H16A	0.9900
C1—H1A	0.9800	C16—H16B	0.9900
C1—H1B	0.9800	C17—C18	1.545 (2)
C1—H1C	0.9800	C17—H17A	0.9900
C2—C3	1.520 (2)	C17—H17B	0.9900
C3—C4	1.551 (2)	C18—C20	1.524 (2)
C3—H3	1.0000	C18—C23	1.545 (2)
C4—C5	1.547 (2)	C18—C19	1.542 (2)
C4—C10	1.556 (2)	C19—H19A	0.9800
C4—H4	1.0000	C19—H19B	0.9800
C5—C7	1.525 (2)	C19—H19C	0.9800
C5—C6	1.531 (2)	C20—C21	1.334 (2)
C5—H5	1.0000	C21—C22	1.468 (2)
C6—H6A	0.9800	C21—H21	0.9500
C6—H6B	0.9800	C23—C24	1.503 (2)
C6—H6C	0.9800	C23—H23	1.0000
C7—C8	1.539 (2)	C24—C27	1.352 (3)
C8—C13	1.527 (2)	C24—C25	1.431 (3)
C8—C9	1.552 (2)	C25—C26	1.350 (3)
C9—C10	1.534 (2)	C25—H25	0.9500
C10—C11	1.536 (2)	C26—H26	0.9500
C10—C12	1.548 (2)	C27—H27	0.9500
C11—H11A	0.9800

C2—O1—C1	116.25 (14)	H12B—C12—H12C	109.5
C3—O3—C7	108.49 (12)	C8—C13—C14	112.08 (13)
C7—O5—C15	114.02 (12)	C8—C13—H13A	109.2
C8—O6—H6	109.5	C14—C13—H13A	109.2
C22—O8—C23	116.86 (14)	C8—C13—H13B	109.2
C26—O9—C27	106.34 (17)	C14—C13—H13B	109.2
O1—C1—H1A	109.5	H13A—C13—H13B	107.9
O1—C1—H1B	109.5	C20—C14—C15	115.40 (14)
H1A—C1—H1B	109.5	C20—C14—C13	116.45 (14)
O1—C1—H1C	109.5	C15—C14—C13	108.80 (13)
H1A—C1—H1C	109.5	C20—C14—H14	105.0
H1B—C1—H1C	109.5	C15—C14—H14	105.0
O2—C2—O1	124.55 (16)	C13—C14—H14	105.0
O2—C2—C3	122.41 (16)	O5—C15—C16	106.52 (14)
O1—C2—C3	113.02 (14)	O5—C15—C14	112.16 (13)
O3—C3—C2	110.89 (13)	C16—C15—C14	113.15 (13)
O3—C3—C4	105.31 (12)	O5—C15—H15	108.3
C2—C3—C4	116.24 (13)	C16—C15—H15	108.3
O3—C3—H3	108.0	C14—C15—H15	108.3
C2—C3—H3	108.0	C15—C16—C17	112.39 (14)
C4—C3—H3	108.0	C15—C16—H16A	109.1
C5—C4—C3	98.39 (12)	C17—C16—H16A	109.1
C5—C4—C10	110.50 (13)	C15—C16—H16B	109.1
C3—C4—C10	115.04 (14)	C17—C16—H16B	109.1
C5—C4—H4	110.8	H16A—C16—H16B	107.9
C3—C4—H4	110.8	C16—C17—C18	112.30 (15)
C10—C4—H4	110.8	C16—C17—H17A	109.1
C7—C5—C6	114.03 (14)	C18—C17—H17A	109.1
C7—C5—C4	98.47 (13)	C16—C17—H17B	109.1
C6—C5—C4	114.11 (14)	C18—C17—H17B	109.1
C7—C5—H5	109.9	H17A—C17—H17B	107.9
C6—C5—H5	109.9	C20—C18—C23	107.41 (13)
C4—C5—H5	109.9	C20—C18—C19	109.36 (14)
C5—C6—H6A	109.5	C23—C18—C19	110.80 (14)
C5—C6—H6B	109.5	C20—C18—C17	109.81 (14)
H6A—C6—H6B	109.5	C23—C18—C17	108.41 (14)
C5—C6—H6C	109.5	C19—C18—C17	110.97 (15)
H6A—C6—H6C	109.5	C18—C19—H19A	109.5
H6B—C6—H6C	109.5	C18—C19—H19B	109.5
O5—C7—O3	109.63 (12)	H19A—C19—H19B	109.5
O5—C7—C5	112.14 (13)	C18—C19—H19C	109.5
O3—C7—C5	104.93 (13)	H19A—C19—H19C	109.5
O5—C7—C8	111.30 (13)	H19B—C19—H19C	109.5
O3—C7—C8	106.12 (12)	C21—C20—C14	122.97 (16)
C5—C7—C8	112.32 (13)	C21—C20—C18	119.08 (15)
O6—C8—C13	112.70 (13)	C14—C20—C18	117.20 (14)
O6—C8—C7	106.58 (12)	C20—C21—C22	122.12 (16)
C13—C8—C7	109.87 (13)	C20—C21—H21	118.9
O6—C8—C9	108.09 (13)	C22—C21—H21	118.9
C13—C8—C9	110.49 (13)	O7—C22—O8	118.50 (17)
C7—C8—C9	108.97 (13)	O7—C22—C21	123.59 (18)
O4—C9—C10	122.19 (15)	O8—C22—C21	117.77 (17)
O4—C9—C8	120.02 (15)	O8—C23—C24	104.80 (14)
C10—C9—C8	117.72 (14)	O8—C23—C18	111.08 (14)
C9—C10—C11	110.56 (14)	C24—C23—C18	115.43 (15)
C9—C10—C12	108.10 (14)	O8—C23—H23	108.4
C11—C10—C12	105.35 (13)	C24—C23—H23	108.4
C9—C10—C4	108.54 (13)	C18—C23—H23	108.4
C11—C10—C4	113.22 (14)	C27—C24—C25	106.02 (18)
C12—C10—C4	110.95 (14)	C27—C24—C23	125.89 (18)
C10—C11—H11A	109.5	C25—C24—C23	128.07 (18)
C10—C11—H11B	109.5	C26—C25—C24	106.4 (2)
H11A—C11—H11B	109.5	C26—C25—H25	126.8
C10—C11—H11C	109.5	C24—C25—H25	126.8
H11A—C11—H11C	109.5	C25—C26—O9	110.73 (19)
H11B—C11—H11C	109.5	C25—C26—H26	124.6
C10—C12—H12A	109.5	O9—C26—H26	124.6
C10—C12—H12B	109.5	C24—C27—O9	110.5 (2)
H12A—C12—H12B	109.5	C24—C27—H27	124.7
C10—C12—H12C	109.5	O9—C27—H27	124.7
H12A—C12—H12C	109.5

C1—O1—C2—O2	5.7 (2)	C3—C4—C10—C12	−169.29 (14)
C1—O1—C2—C3	−172.55 (15)	O6—C8—C13—C14	66.52 (17)
C7—O3—C3—C2	138.99 (13)	C7—C8—C13—C14	−52.18 (17)
C7—O3—C3—C4	12.48 (16)	C9—C8—C13—C14	−172.45 (13)
O2—C2—C3—O3	158.88 (15)	C8—C13—C14—C20	−81.44 (18)
O1—C2—C3—O3	−22.83 (19)	C8—C13—C14—C15	51.05 (18)
O2—C2—C3—C4	−80.9 (2)	C7—O5—C15—C16	−176.46 (13)
O1—C2—C3—C4	97.37 (17)	C7—O5—C15—C14	59.23 (17)
O3—C3—C4—C5	−37.89 (15)	C20—C14—C15—O5	80.22 (17)
C2—C3—C4—C5	−161.05 (14)	C13—C14—C15—O5	−52.82 (17)
O3—C3—C4—C10	79.47 (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—C7	47.08 (14)	O5—C15—C16—C17	−74.21 (17)
C10—C4—C5—C7	−73.71 (15)	C14—C15—C16—C17	49.5 (2)
C3—C4—C5—C6	−74.10 (17)	C15—C16—C17—C18	−57.93 (19)
C10—C4—C5—C6	165.11 (15)	C16—C17—C18—C20	54.44 (19)
C15—O5—C7—O3	57.64 (17)	C16—C17—C18—C23	171.52 (13)
C15—O5—C7—C5	173.77 (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—O5	139.56 (13)	C13—C14—C20—C21	−20.6 (2)
C3—O3—C7—C5	18.95 (16)	C15—C14—C20—C18	40.0 (2)
C3—O3—C7—C8	−100.14 (14)	C13—C14—C20—C18	169.39 (14)
C6—C5—C7—O5	−39.71 (19)	C23—C18—C20—C21	25.9 (2)
C4—C5—C7—O5	−160.94 (13)	C19—C18—C20—C21	−94.40 (19)
C6—C5—C7—O3	79.23 (16)	C17—C18—C20—C21	143.61 (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—C14	75.99 (18)
C4—C5—C7—C8	72.83 (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—O6	173.53 (12)	C18—C20—C21—C22	9.5 (3)
C5—C7—C8—O6	59.42 (16)	C23—O8—C22—O7	170.30 (18)
O5—C7—C8—C13	55.14 (17)	C23—O8—C22—C21	−13.9 (2)
O3—C7—C8—C13	−64.08 (15)	C20—C21—C22—O7	157.6 (2)
C5—C7—C8—C13	−178.18 (13)	C20—C21—C22—O8	−18.0 (3)
O5—C7—C8—C9	176.32 (12)	C22—O8—C23—C24	175.76 (15)
O3—C7—C8—C9	57.11 (15)	C22—O8—C23—C18	50.5 (2)
C5—C7—C8—C9	−57.00 (17)	C20—C18—C23—O8	−54.44 (18)
O6—C8—C9—O4	100.48 (17)	C19—C18—C23—O8	64.95 (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—C10	159.65 (14)	C17—C18—C23—C24	67.85 (19)
C7—C8—C9—C10	38.84 (18)	O8—C23—C24—C27	−23.5 (3)
O4—C9—C10—C11	17.8 (2)	C18—C23—C24—C27	99.1 (2)
C8—C9—C10—C11	−165.21 (13)	O8—C23—C24—C25	158.54 (18)
O4—C9—C10—C12	−97.08 (19)	C18—C23—C24—C25	−78.9 (2)
C8—C9—C10—C12	79.95 (17)	C27—C24—C25—C26	0.2 (2)
O4—C9—C10—C4	142.50 (16)	C23—C24—C25—C26	178.52 (18)
C8—C9—C10—C4	−40.47 (19)	C24—C25—C26—O9	0.1 (2)
C5—C4—C10—C9	59.63 (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—C11	72.50 (17)	C26—O9—C27—C24	0.5 (2)
C5—C4—C10—C12	−59.01 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O2ⁱ	0.84	2.01	2.854 (2)	178

Symmetry code: (i) −x+2, y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₇H₃₂O₉
M_r	500.53
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	123
a, b, c (Å)	8.8326 (1), 12.8977 (2), 11.1555 (1)
β (°)	110.777 (1)
V (Å³)	1188.19 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.40 × 0.30 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11333, 2856, 2760
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.083, 1.03
No. of reflections	2856
No. of parameters	331
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
O6—H6···O2ⁱ	0.84	2.01	2.854 (2)	178

Symmetry code: (i) −x+2, y−1/2, −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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