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

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ISSN: 2056-9890

Swietenolide di­acetate from the seeds of Swietenia macrophylla

aInstitute of Biological Sciences, University of Malaya, 50603 Kuala Lumpur, Malaysia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 4 May 2010; accepted 14 May 2010; online 22 May 2010)

The title compound, C31H38O10 [systematic name: (αR,4R,4aR,6aS,7R,8S,10R,11S)-methyl α,10-di­acet­oxy-4-(3-furyl)-4a,7,9,9-tetra­methyl-2,13-dioxo-1,4,4a,5,6,6a,7,8,9,10,11,12-dodeca­hydro-7,11-methano-2H-cyclo­octa­[f][2]benzo­pyran-8-acetate], was isolated from the seeds of Swietenia macrophylla. The mol­ecule contains four six-membered rings connected together in the shape of a bowl; one of the inner rings adopts a twisted chair conformation owing to the carbon–carbon double bond. The furyl substitutent is connected to an outer ring, and it points away from the bowl cavity.

Related literature

For the isolation, spectroscopic characterization and absolute structure of the title compound, see: Chan et al. (1976[Chan, K. C., Tang, T. S. & Toh, H. T. (1976). Phytochemistry, 15, 429-430.]); Connolly & Labbe (1980[Connolly, J. D. & Labbe, C. (1980). J. Chem. Soc. Perkin Trans. 1, pp. 529-530.]); Connolly et al. (1965[Connolly, J. D., McCrindle, R., Overton, K. H. & Warnock, W. D. C. (1965). Tetrahedron Lett. pp. 2937-2940.]); Govindachari et al. (1999[Govindachari, T. R., Suresh, G., Banumathy, B., Masilamani, S., Gopala­krish­nan, G. & Kumari, G. N. K. (1999). J. Chem. Ecol. 25, 923-933.]); Kadota, Marpaung et al. (1990[Kadota, S., Marpaung, L., Kikuchi, T. & Ekimoto, H. (1990). Chem. Pharm. Bull. 38, 639-651.]); Kadota, Yanagawa et al. (1990[Kadota, S., Yanagawa, K., Kikuchi, T. & Tanaka, K. (1990). Tetrahedron Lett. 31, 5943-5946.]); Mootoo et al. (1999[Mootoo, B. S., Ali, A., Motilal, R., Pingal, R., Ramlal, A., Khan, A., Reynolds, W. F. & McLean, S. (1999). J. Nat. Prod. 62, 1514-1517.]); Narender et al. (2008[Narender,T., Khaliq, T. Shweta (2008). Nat. Prod. Res. A22, 763-800.]); Schefer et al. (2006[Schefer, A. B., Braumann, U., Tseng, L.-H., Spraul, M., Soares, M. G., Fernandes, J. B., da Silva, M. F. G. F., Vieira, P. C. & Ferreira, A. G. (2006). J. Chromatograph. A, 1128, 152-163.]); Taylor & Taylor (1983[Taylor, A. R. H. & Taylor, D. A. H. (1983). S. Afr. Phytochem. 22, 2870-2871.]); Yuan et al. (2010[Yuan, T., Zhang, C.-R., Yang, S.-P. & Yue, J.-M. (2010). J. Nat. Prod. 73, 669-674.]).

[Scheme 1]

Experimental

Crystal data
  • C31H38O10

  • Mr = 570.61

  • Orthorhombic, P 21 21 21

  • a = 12.5889 (11) Å

  • b = 13.7109 (12) Å

  • c = 17.0045 (14) Å

  • V = 2935.1 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.35 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART APEX diffractometer

  • 28065 measured reflections

  • 3771 independent reflections

  • 2491 reflections with I > 2σ(I)

  • Rint = 0.077

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.127

  • S = 1.02

  • 3771 reflections

  • 377 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.13 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. Submitted.]).

Supporting information


Comment top

Sweietenia macrophylla is a large mahogany tree growing in the rainforests of Malaysia. The extracts of the seeds contain flavonoids, saponins and alkaloids that are commecialized in local herbal products. The isolation of the title compound (Scheme I, Fig. 1) has been reported a long time ago. The present crystal structure analysis confirms the spectroscopic structure determination.

Related literature top

For the isolation and spectroscopic characterization of the title compound, see: Chan et al. (1976); Connolly & Labbe (1980); Connolly et al. (1965); Govindachari et al. (1999); Kadota, Marpaung et al. (1990); Kadota, Yanagawa et al. (1990); Mootoo et al. (1999); Narender et al. (2008); Schefer et al. (2006); Taylor & Taylor (1983); Yuan et al. (2010).

Experimental top

Swietenolide diacetate was isloated from the seeds of Swietenia macrophylla by using a reported procedure (Chan et al., 1976).

The finely ground seeds (600 g) were soaked in ethanol at room temperature for three days. The mixture was filtered and the sovlent evaporated to give a dark yellow crude material (70 g). A portion (40 g) was successively extracted with n-hexane, ethyl acetate and water to give an n-hexane-insoluble residue. The residue was partitioned between ethyl acetate-water (1:1) to give an ethyl acetate-soluble fraction (30 g, 80%).

This fraction (3 g) was subjected to column chromatography on silica gel (70-230 mesh, 300 g), with initial elution by n-hexane, followed by increasing proportions of chloroform. Eleven fractions were obtained. The fourth fraction (2 g) was further subjected to column chromatography (70-230 mesh,200 g), initially eluting with n-hexane and later with acetone to give twelve fractions.

The eighth fraction (600 mg) was dissolved in methanol and kept in a refrigerator. A white solid was obtained after two days, and a second crop was obtained after another two days. Recrystallization of the first crop from chloroform yielded colorless crystals of the title compound (yield 15 mg).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5Ueq(C). The Flack parameter was fixed to be zero. 2976 Friedel pairs were merged.

Structure description top

Sweietenia macrophylla is a large mahogany tree growing in the rainforests of Malaysia. The extracts of the seeds contain flavonoids, saponins and alkaloids that are commecialized in local herbal products. The isolation of the title compound (Scheme I, Fig. 1) has been reported a long time ago. The present crystal structure analysis confirms the spectroscopic structure determination.

For the isolation and spectroscopic characterization of the title compound, see: Chan et al. (1976); Connolly & Labbe (1980); Connolly et al. (1965); Govindachari et al. (1999); Kadota, Marpaung et al. (1990); Kadota, Yanagawa et al. (1990); Mootoo et al. (1999); Narender et al. (2008); Schefer et al. (2006); Taylor & Taylor (1983); Yuan et al. (2010).

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 C31H38O10 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
(αR,4R,4aR,6aS,7R,8S,10R, 11S)-Methyl α,10-diacetoxy-4-(3-furyl)-4a,7,9,9-tetramethyl-2,13-dioxo- 1,4,4a,5,6,6a,7,8,9,10,11,12-dodecahydro-7,11-methano-2H- cycloocta[f][2]benzopyran-8-acetate top
Crystal data top
C31H38O10F(000) = 1216
Mr = 570.61Dx = 1.291 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4600 reflections
a = 12.5889 (11) Åθ = 2.2–21.7°
b = 13.7109 (12) ŵ = 0.10 mm1
c = 17.0045 (14) ÅT = 293 K
V = 2935.1 (4) Å3Prism, colorless
Z = 40.35 × 0.15 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer
2491 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.077
Graphite monochromatorθmax = 27.5°, θmin = 1.9°
ω scansh = 1416
28065 measured reflectionsk = 1717
3771 independent reflectionsl = 2122
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0642P)2 + 0.2454P]
where P = (Fo2 + 2Fc2)/3
3771 reflections(Δ/σ)max = 0.001
377 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C31H38O10V = 2935.1 (4) Å3
Mr = 570.61Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 12.5889 (11) ŵ = 0.10 mm1
b = 13.7109 (12) ÅT = 293 K
c = 17.0045 (14) Å0.35 × 0.15 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer
2491 reflections with I > 2σ(I)
28065 measured reflectionsRint = 0.077
3771 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.02Δρmax = 0.16 e Å3
3771 reflectionsΔρmin = 0.13 e Å3
377 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6572 (2)0.3236 (2)0.20580 (14)0.0747 (7)
O20.7345 (2)0.35757 (17)0.04692 (14)0.0651 (6)
O30.7606 (3)0.4265 (2)0.16075 (17)0.0924 (9)
O40.9749 (2)0.1523 (2)0.17405 (16)0.0828 (8)
O50.55375 (19)0.11379 (15)0.08732 (13)0.0571 (6)
O60.61162 (19)0.03581 (15)0.06055 (15)0.0622 (6)
O70.72148 (19)0.20206 (14)0.03800 (12)0.0521 (5)
O80.7631 (3)0.19051 (19)0.16536 (15)0.0807 (8)
O90.6687 (2)0.0434 (2)0.19007 (13)0.0720 (7)
O100.5727 (4)0.0137 (4)0.2958 (3)0.169 (2)
C10.6620 (3)0.2682 (3)0.13924 (19)0.0620 (9)
H10.62690.20910.13250.074*
C20.7183 (4)0.4023 (3)0.1918 (2)0.0801 (12)
H20.72960.45270.22740.096*
C30.7605 (4)0.3985 (3)0.1201 (2)0.0729 (11)
H30.80530.44450.09750.087*
C40.7242 (3)0.3105 (2)0.08472 (19)0.0520 (8)
C50.7473 (3)0.2725 (2)0.00418 (18)0.0491 (7)
H50.69230.22480.00950.059*
C60.7706 (3)0.3546 (3)0.1211 (2)0.0622 (9)
C70.8189 (4)0.2635 (3)0.1517 (2)0.0704 (11)
H7A0.76720.23210.18560.084*
H7B0.87900.28140.18440.084*
C80.8569 (3)0.1887 (2)0.09253 (17)0.0486 (7)
C90.8563 (2)0.2247 (2)0.00792 (16)0.0431 (7)
C100.9466 (3)0.2977 (2)0.0049 (2)0.0582 (8)
H10A1.01360.26510.00110.087*
H10B0.94120.34930.03300.087*
H10C0.94160.32440.05700.087*
C110.8891 (3)0.0997 (2)0.11439 (17)0.0481 (7)
C120.9384 (2)0.0273 (2)0.05864 (17)0.0485 (7)
H121.01070.01710.07840.058*
C130.9526 (3)0.0679 (2)0.02434 (17)0.0510 (7)
H13A1.02070.10090.02730.061*
H13B0.95430.01400.06130.061*
C140.8658 (2)0.1386 (2)0.04903 (16)0.0455 (7)
H14A0.79850.10430.05120.055*
H14B0.88120.16300.10130.055*
C150.8823 (2)0.0758 (2)0.06588 (17)0.0490 (7)
C160.9398 (3)0.1515 (3)0.0156 (2)0.0609 (9)
H16A0.91020.21490.02540.091*
H16B1.01400.15180.02870.091*
H16C0.93150.13540.03900.091*
C170.7588 (2)0.0670 (2)0.05172 (17)0.0438 (7)
H170.74460.00330.05370.053*
C180.7268 (3)0.09720 (19)0.03206 (16)0.0432 (7)
H180.78360.07550.06730.052*
C190.6247 (3)0.0503 (2)0.06065 (16)0.0443 (7)
C200.4543 (3)0.0743 (3)0.1149 (2)0.0680 (10)
H20A0.41840.12220.14640.102*
H20B0.46770.01720.14600.102*
H20C0.41070.05720.07070.102*
C210.7431 (3)0.2402 (2)0.1093 (2)0.0565 (8)
C220.7397 (4)0.3485 (2)0.1083 (3)0.0834 (13)
H22A0.80300.37380.13220.125*
H22B0.67870.37060.13710.125*
H22C0.73510.37090.05490.125*
C230.6916 (3)0.1102 (3)0.12000 (18)0.0590 (9)
C240.5717 (3)0.1013 (3)0.1041 (2)0.0760 (11)
H24A0.53310.11580.15130.114*
H24B0.55170.14650.06360.114*
H24C0.55560.03610.08740.114*
C250.7149 (4)0.2193 (3)0.1370 (2)0.0815 (13)
H25A0.79010.22860.14260.122*
H25B0.68930.25840.09410.122*
H25C0.67970.23850.18460.122*
C260.7198 (3)0.0507 (3)0.19481 (19)0.0641 (9)
H260.69010.08520.24020.077*
C270.8403 (3)0.0385 (3)0.20878 (18)0.0599 (9)
H270.85630.06060.26230.072*
C280.8853 (3)0.0659 (3)0.19881 (18)0.0620 (9)
H28A0.84180.11090.22880.074*
H28B0.95660.06790.22050.074*
C290.9034 (3)0.0992 (3)0.1525 (2)0.0599 (9)
C300.5932 (4)0.0658 (5)0.2431 (3)0.0993 (16)
C310.5422 (5)0.1596 (5)0.2259 (3)0.135 (3)
H31A0.47200.14840.20580.203*
H31B0.58330.19430.18750.203*
H31C0.53790.19760.27330.203*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0871 (19)0.0801 (18)0.0570 (15)0.0094 (16)0.0090 (14)0.0018 (13)
O20.0688 (15)0.0690 (14)0.0576 (14)0.0173 (13)0.0014 (12)0.0152 (12)
O30.123 (2)0.0782 (17)0.0757 (18)0.0140 (19)0.0052 (17)0.0303 (15)
O40.0820 (18)0.0923 (19)0.0742 (17)0.0214 (17)0.0234 (15)0.0242 (16)
O50.0546 (13)0.0524 (12)0.0643 (14)0.0015 (11)0.0160 (12)0.0047 (10)
O60.0572 (14)0.0449 (12)0.0844 (16)0.0046 (10)0.0142 (13)0.0017 (11)
O70.0649 (14)0.0394 (10)0.0521 (12)0.0058 (10)0.0030 (11)0.0013 (9)
O80.119 (2)0.0714 (15)0.0516 (15)0.0022 (17)0.0051 (15)0.0070 (13)
O90.0713 (16)0.103 (2)0.0417 (12)0.0149 (15)0.0016 (12)0.0055 (12)
O100.176 (5)0.226 (5)0.103 (3)0.026 (4)0.082 (3)0.017 (3)
C10.070 (2)0.064 (2)0.0519 (19)0.0011 (19)0.0007 (18)0.0028 (17)
C20.098 (3)0.065 (2)0.077 (3)0.011 (2)0.005 (3)0.014 (2)
C30.093 (3)0.0507 (19)0.075 (3)0.004 (2)0.019 (2)0.0056 (17)
C40.0514 (19)0.0491 (17)0.0555 (19)0.0085 (15)0.0043 (16)0.0057 (14)
C50.0475 (19)0.0506 (17)0.0493 (17)0.0008 (15)0.0021 (14)0.0059 (14)
C60.067 (2)0.066 (2)0.054 (2)0.0016 (19)0.0086 (18)0.0122 (17)
C70.099 (3)0.066 (2)0.0456 (18)0.001 (2)0.0063 (19)0.0097 (16)
C80.0516 (18)0.0564 (18)0.0377 (15)0.0057 (15)0.0005 (14)0.0047 (14)
C90.0406 (16)0.0487 (16)0.0400 (15)0.0035 (13)0.0003 (13)0.0020 (13)
C100.0514 (19)0.063 (2)0.060 (2)0.0124 (17)0.0019 (17)0.0026 (17)
C110.0483 (18)0.0587 (18)0.0374 (15)0.0050 (16)0.0054 (14)0.0009 (13)
C120.0408 (16)0.0629 (18)0.0419 (15)0.0054 (15)0.0063 (15)0.0020 (15)
C130.0502 (18)0.0547 (17)0.0481 (17)0.0027 (16)0.0063 (15)0.0004 (14)
C140.0504 (17)0.0508 (16)0.0353 (13)0.0019 (14)0.0025 (14)0.0018 (13)
C150.0468 (17)0.0568 (17)0.0435 (16)0.0072 (15)0.0059 (14)0.0059 (14)
C160.058 (2)0.0603 (19)0.064 (2)0.0185 (18)0.0057 (18)0.0014 (17)
C170.0451 (17)0.0465 (15)0.0397 (14)0.0014 (14)0.0031 (13)0.0044 (13)
C180.0523 (17)0.0366 (14)0.0407 (15)0.0025 (14)0.0043 (14)0.0012 (12)
C190.0543 (18)0.0414 (16)0.0372 (14)0.0011 (14)0.0023 (14)0.0008 (12)
C200.055 (2)0.080 (2)0.069 (2)0.002 (2)0.0195 (19)0.0008 (19)
C210.056 (2)0.0523 (18)0.061 (2)0.0036 (17)0.0063 (17)0.0084 (16)
C220.092 (3)0.052 (2)0.106 (3)0.009 (2)0.005 (3)0.022 (2)
C230.064 (2)0.070 (2)0.0426 (17)0.0084 (18)0.0010 (16)0.0080 (15)
C240.059 (2)0.116 (3)0.053 (2)0.016 (2)0.0049 (18)0.010 (2)
C250.096 (3)0.081 (3)0.067 (2)0.022 (2)0.007 (2)0.029 (2)
C260.067 (2)0.086 (2)0.0386 (17)0.005 (2)0.0029 (17)0.0158 (16)
C270.070 (2)0.076 (2)0.0341 (15)0.0009 (19)0.0117 (16)0.0160 (15)
C280.072 (2)0.075 (2)0.0385 (16)0.000 (2)0.0092 (16)0.0015 (16)
C290.061 (2)0.063 (2)0.056 (2)0.0001 (18)0.0147 (17)0.0156 (17)
C300.087 (3)0.162 (5)0.049 (2)0.010 (4)0.008 (2)0.016 (3)
C310.100 (4)0.208 (7)0.099 (4)0.070 (5)0.027 (3)0.056 (4)
Geometric parameters (Å, º) top
O1—C21.347 (5)C13—H13B0.9700
O1—C11.364 (4)C14—H14A0.9700
O2—C61.342 (4)C14—H14B0.9700
O2—C51.463 (4)C15—C161.528 (5)
O3—C61.200 (4)C15—C291.531 (5)
O4—C291.214 (4)C15—C171.578 (4)
O5—C191.327 (3)C16—H16A0.9600
O5—C201.442 (4)C16—H16B0.9600
O6—C191.193 (3)C16—H16C0.9600
O7—C211.348 (4)C17—C181.538 (4)
O7—C181.443 (3)C17—C231.554 (4)
O8—C211.198 (4)C17—H170.9800
O9—C301.345 (5)C18—C191.517 (4)
O9—C261.445 (5)C18—H180.9800
O10—C301.175 (7)C20—H20A0.9600
C1—C41.345 (5)C20—H20B0.9600
C1—H10.9300C20—H20C0.9600
C2—C31.330 (5)C21—C221.486 (5)
C2—H20.9300C22—H22A0.9600
C3—C41.423 (5)C22—H22B0.9600
C3—H30.9300C22—H22C0.9600
C4—C51.494 (5)C23—C241.538 (5)
C5—C91.535 (4)C23—C261.552 (5)
C5—H50.9800C23—C251.552 (5)
C6—C71.484 (5)C24—H24A0.9600
C7—C81.514 (4)C24—H24B0.9600
C7—H7A0.9700C24—H24C0.9600
C7—H7B0.9700C25—H25A0.9600
C8—C111.339 (4)C25—H25B0.9600
C8—C91.521 (4)C25—H25C0.9600
C9—C101.530 (4)C26—C271.544 (5)
C9—C141.532 (4)C26—H260.9800
C10—H10A0.9600C27—C291.497 (5)
C10—H10B0.9600C27—C281.549 (5)
C10—H10C0.9600C27—H270.9800
C11—C121.506 (4)C28—H28A0.9700
C11—C281.509 (4)C28—H28B0.9700
C12—C131.528 (4)C30—C311.467 (8)
C12—C151.585 (4)C31—H31A0.9600
C12—H120.9800C31—H31B0.9600
C13—C141.520 (4)C31—H31C0.9600
C13—H13A0.9700
C2—O1—C1105.9 (3)H16B—C16—H16C109.5
C6—O2—C5119.8 (3)C18—C17—C23116.6 (3)
C19—O5—C20116.7 (2)C18—C17—C15112.3 (2)
C21—O7—C18116.1 (2)C23—C17—C15113.1 (2)
C30—O9—C26118.8 (4)C18—C17—H17104.5
C4—C1—O1111.0 (3)C23—C17—H17104.5
C4—C1—H1124.5C15—C17—H17104.5
O1—C1—H1124.5O7—C18—C19111.1 (2)
C3—C2—O1111.0 (4)O7—C18—C17110.2 (2)
C3—C2—H2124.5C19—C18—C17113.9 (2)
O1—C2—H2124.5O7—C18—H18107.1
C2—C3—C4107.0 (4)C19—C18—H18107.1
C2—C3—H3126.5C17—C18—H18107.1
C4—C3—H3126.5O6—C19—O5123.8 (3)
C1—C4—C3105.1 (3)O6—C19—C18122.4 (3)
C1—C4—C5126.5 (3)O5—C19—C18113.7 (2)
C3—C4—C5128.4 (3)O5—C20—H20A109.5
O2—C5—C4104.2 (2)O5—C20—H20B109.5
O2—C5—C9111.0 (2)H20A—C20—H20B109.5
C4—C5—C9116.5 (3)O5—C20—H20C109.5
O2—C5—H5108.3H20A—C20—H20C109.5
C4—C5—H5108.3H20B—C20—H20C109.5
C9—C5—H5108.3O8—C21—O7122.5 (3)
O3—C6—O2117.9 (3)O8—C21—C22125.7 (3)
O3—C6—C7122.5 (3)O7—C21—C22111.8 (3)
O2—C6—C7119.6 (3)C21—C22—H22A109.5
C6—C7—C8117.8 (3)C21—C22—H22B109.5
C6—C7—H7A107.8H22A—C22—H22B109.5
C8—C7—H7A107.8C21—C22—H22C109.5
C6—C7—H7B107.8H22A—C22—H22C109.5
C8—C7—H7B107.8H22B—C22—H22C109.5
H7A—C7—H7B107.2C24—C23—C26109.1 (3)
C11—C8—C7121.9 (3)C24—C23—C25107.1 (3)
C11—C8—C9124.0 (3)C26—C23—C25108.1 (3)
C7—C8—C9114.0 (3)C24—C23—C17111.9 (3)
C8—C9—C10110.1 (2)C26—C23—C17106.7 (3)
C8—C9—C14110.3 (2)C25—C23—C17113.8 (3)
C10—C9—C14110.8 (2)C23—C24—H24A109.5
C8—C9—C5105.6 (2)C23—C24—H24B109.5
C10—C9—C5111.5 (2)H24A—C24—H24B109.5
C14—C9—C5108.3 (2)C23—C24—H24C109.5
C9—C10—H10A109.5H24A—C24—H24C109.5
C9—C10—H10B109.5H24B—C24—H24C109.5
H10A—C10—H10B109.5C23—C25—H25A109.5
C9—C10—H10C109.5C23—C25—H25B109.5
H10A—C10—H10C109.5H25A—C25—H25B109.5
H10B—C10—H10C109.5C23—C25—H25C109.5
C8—C11—C12123.4 (3)H25A—C25—H25C109.5
C8—C11—C28122.3 (3)H25B—C25—H25C109.5
C12—C11—C28114.2 (3)O9—C26—C27110.4 (3)
C11—C12—C13112.9 (3)O9—C26—C23108.8 (3)
C11—C12—C15110.8 (2)C27—C26—C23114.1 (3)
C13—C12—C15116.7 (3)O9—C26—H26107.8
C11—C12—H12105.1C27—C26—H26107.8
C13—C12—H12105.1C23—C26—H26107.8
C15—C12—H12105.1C29—C27—C26111.3 (3)
C14—C13—C12113.8 (3)C29—C27—C28104.4 (3)
C14—C13—H13A108.8C26—C27—C28116.3 (3)
C12—C13—H13A108.8C29—C27—H27108.2
C14—C13—H13B108.8C26—C27—H27108.2
C12—C13—H13B108.8C28—C27—H27108.2
H13A—C13—H13B107.7C11—C28—C27113.5 (3)
C13—C14—C9111.9 (2)C11—C28—H28A108.9
C13—C14—H14A109.2C27—C28—H28A108.9
C9—C14—H14A109.2C11—C28—H28B108.9
C13—C14—H14B109.2C27—C28—H28B108.9
C9—C14—H14B109.2H28A—C28—H28B107.7
H14A—C14—H14B107.9O4—C29—C27122.3 (3)
C16—C15—C29108.3 (3)O4—C29—C15123.0 (3)
C16—C15—C17115.7 (3)C27—C29—C15114.0 (3)
C29—C15—C17109.6 (3)O10—C30—O9121.8 (6)
C16—C15—C12110.5 (3)O10—C30—C31126.1 (5)
C29—C15—C12100.6 (3)O9—C30—C31112.1 (5)
C17—C15—C12111.0 (2)C30—C31—H31A109.5
C15—C16—H16A109.5C30—C31—H31B109.5
C15—C16—H16B109.5H31A—C31—H31B109.5
H16A—C16—H16B109.5C30—C31—H31C109.5
C15—C16—H16C109.5H31A—C31—H31C109.5
H16A—C16—H16C109.5H31B—C31—H31C109.5
C2—O1—C1—C40.0 (4)C12—C15—C17—C18100.0 (3)
C1—O1—C2—C30.0 (5)C16—C15—C17—C23107.4 (3)
O1—C2—C3—C40.0 (5)C29—C15—C17—C2315.4 (4)
O1—C1—C4—C30.0 (4)C12—C15—C17—C23125.6 (3)
O1—C1—C4—C5179.0 (3)C21—O7—C18—C1982.4 (3)
C2—C3—C4—C10.0 (4)C21—O7—C18—C17150.4 (3)
C2—C3—C4—C5179.0 (3)C23—C17—C18—O752.8 (3)
C6—O2—C5—C4166.2 (3)C15—C17—C18—O780.0 (3)
C6—O2—C5—C940.0 (4)C23—C17—C18—C1972.9 (3)
C1—C4—C5—O2134.2 (3)C15—C17—C18—C19154.4 (2)
C3—C4—C5—O244.6 (4)C20—O5—C19—O62.2 (4)
C1—C4—C5—C9103.2 (4)C20—O5—C19—C18179.5 (3)
C3—C4—C5—C978.0 (4)O7—C18—C19—O6179.6 (3)
C5—O2—C6—O3178.5 (3)C17—C18—C19—O654.4 (4)
C5—O2—C6—C72.7 (5)O7—C18—C19—O52.1 (3)
O3—C6—C7—C8162.5 (4)C17—C18—C19—O5127.3 (3)
O2—C6—C7—C818.8 (5)C18—O7—C21—O81.8 (5)
C6—C7—C8—C11171.5 (3)C18—O7—C21—C22177.7 (3)
C6—C7—C8—C99.4 (5)C18—C17—C23—C2447.1 (4)
C11—C8—C9—C10106.3 (3)C15—C17—C23—C24179.4 (3)
C7—C8—C9—C1072.8 (4)C18—C17—C23—C26166.3 (3)
C11—C8—C9—C1416.4 (4)C15—C17—C23—C2661.3 (4)
C7—C8—C9—C14164.5 (3)C18—C17—C23—C2574.5 (4)
C11—C8—C9—C5133.3 (3)C15—C17—C23—C2557.9 (4)
C7—C8—C9—C547.7 (3)C30—O9—C26—C27119.0 (4)
O2—C5—C9—C863.6 (3)C30—O9—C26—C23115.2 (4)
C4—C5—C9—C8177.4 (3)C24—C23—C26—O945.9 (4)
O2—C5—C9—C1055.9 (3)C25—C23—C26—O9162.1 (3)
C4—C5—C9—C1063.0 (3)C17—C23—C26—O975.1 (3)
O2—C5—C9—C14178.1 (2)C24—C23—C26—C27169.6 (3)
C4—C5—C9—C1459.2 (3)C25—C23—C26—C2774.2 (4)
C7—C8—C11—C12173.2 (3)C17—C23—C26—C2748.6 (4)
C9—C8—C11—C125.9 (5)O9—C26—C27—C29130.9 (3)
C7—C8—C11—C282.8 (5)C23—C26—C27—C298.0 (4)
C9—C8—C11—C28178.1 (3)O9—C26—C27—C2811.4 (4)
C8—C11—C12—C132.8 (4)C23—C26—C27—C28111.4 (4)
C28—C11—C12—C13173.5 (3)C8—C11—C28—C27135.0 (3)
C8—C11—C12—C15130.2 (3)C12—C11—C28—C2748.6 (4)
C28—C11—C12—C1553.5 (3)C29—C27—C28—C1151.4 (4)
C11—C12—C13—C1433.9 (4)C26—C27—C28—C1171.7 (4)
C15—C12—C13—C1496.2 (3)C26—C27—C29—O4130.9 (4)
C12—C13—C14—C957.0 (3)C28—C27—C29—O4102.9 (4)
C8—C9—C14—C1346.3 (3)C26—C27—C29—C1558.6 (4)
C10—C9—C14—C1376.0 (3)C28—C27—C29—C1567.7 (4)
C5—C9—C14—C13161.5 (2)C16—C15—C29—O417.0 (5)
C11—C12—C15—C16174.1 (2)C17—C15—C29—O4144.1 (3)
C13—C12—C15—C1654.8 (3)C12—C15—C29—O498.9 (4)
C11—C12—C15—C2959.9 (3)C16—C15—C29—C27172.5 (3)
C13—C12—C15—C29169.0 (3)C17—C15—C29—C2745.4 (4)
C11—C12—C15—C1756.0 (3)C12—C15—C29—C2771.6 (3)
C13—C12—C15—C1775.1 (3)C26—O9—C30—O104.9 (7)
C16—C15—C17—C1827.1 (4)C26—O9—C30—C31174.6 (4)
C29—C15—C17—C18149.8 (3)

Experimental details

Crystal data
Chemical formulaC31H38O10
Mr570.61
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)12.5889 (11), 13.7109 (12), 17.0045 (14)
V3)2935.1 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.35 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
28065, 3771, 2491
Rint0.077
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.127, 1.02
No. of reflections3771
No. of parameters377
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.13

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 for supporting this study.

References

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