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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 May 22;66(Pt 6):o1396. doi: 10.1107/S1600536810017733

Swietenolide diacetate from the seeds of Swietenia macrophylla

Bey Hing Goh a, Habsah Abdul Kadir a, Sri Nurestri Abdul Malek a, Seik Weng Ng b,*
PMCID: PMC2979530  PMID: 21579475

Abstract

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 ▶); 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 ▶).graphic file with name e-66-o1396-scheme1.jpg

Experimental

Crystal data

  • C31H38O10

  • M r = 570.61

  • Orthorhombic, Inline graphic

  • 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)

  • R int = 0.077

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043

  • wR(F 2) = 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 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017733/bt5263sup1.cif

e-66-o1396-sup1.cif (27.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017733/bt5263Isup2.hkl

e-66-o1396-Isup2.hkl (184.9KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.

Fig. 1.

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Anisotropic displacement ellipsoid plot (Barbour, 2001) of C31H38O10 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C31H38O10 F(000) = 1216
Mr = 570.61 Dx = 1.291 Mg m−3
Orthorhombic, P212121 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab Cell parameters from 4600 reflections
a = 12.5889 (11) Å θ = 2.2–21.7°
b = 13.7109 (12) Å µ = 0.10 mm−1
c = 17.0045 (14) Å T = 293 K
V = 2935.1 (4) Å3 Prism, colorless
Z = 4 0.35 × 0.15 × 0.10 mm
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Data collection

Bruker SMART APEX diffractometer 2491 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.077
graphite θmax = 27.5°, θmin = 1.9°
ω scans h = −14→16
28065 measured reflections k = −17→17
3771 independent reflections l = −21→22
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Refinement

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)] = 0.043 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127 H-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 parameters Δρmax = 0.16 e Å−3
0 restraints Δρmin = −0.13 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.6572 (2) 0.3236 (2) −0.20580 (14) 0.0747 (7)
O2 0.7345 (2) 0.35757 (17) 0.04692 (14) 0.0651 (6)
O3 0.7606 (3) 0.4265 (2) 0.16075 (17) 0.0924 (9)
O4 0.9749 (2) −0.1523 (2) 0.17405 (16) 0.0828 (8)
O5 0.55375 (19) −0.11379 (15) −0.08732 (13) 0.0571 (6)
O6 0.61162 (19) 0.03581 (15) −0.06055 (15) 0.0622 (6)
O7 0.72148 (19) −0.20206 (14) −0.03800 (12) 0.0521 (5)
O8 0.7631 (3) −0.19051 (19) −0.16536 (15) 0.0807 (8)
O9 0.6687 (2) 0.0434 (2) 0.19007 (13) 0.0720 (7)
O10 0.5727 (4) 0.0137 (4) 0.2958 (3) 0.169 (2)
C1 0.6620 (3) 0.2682 (3) −0.13924 (19) 0.0620 (9)
H1 0.6269 0.2091 −0.1325 0.074*
C2 0.7183 (4) 0.4023 (3) −0.1918 (2) 0.0801 (12)
H2 0.7296 0.4527 −0.2274 0.096*
C3 0.7605 (4) 0.3985 (3) −0.1201 (2) 0.0729 (11)
H3 0.8053 0.4445 −0.0975 0.087*
C4 0.7242 (3) 0.3105 (2) −0.08472 (19) 0.0520 (8)
C5 0.7473 (3) 0.2725 (2) −0.00418 (18) 0.0491 (7)
H5 0.6923 0.2248 0.0095 0.059*
C6 0.7706 (3) 0.3546 (3) 0.1211 (2) 0.0622 (9)
C7 0.8189 (4) 0.2635 (3) 0.1517 (2) 0.0704 (11)
H7A 0.7672 0.2321 0.1856 0.084*
H7B 0.8790 0.2814 0.1844 0.084*
C8 0.8569 (3) 0.1887 (2) 0.09253 (17) 0.0486 (7)
C9 0.8563 (2) 0.2247 (2) 0.00792 (16) 0.0431 (7)
C10 0.9466 (3) 0.2977 (2) −0.0049 (2) 0.0582 (8)
H10A 1.0136 0.2651 0.0011 0.087*
H10B 0.9412 0.3493 0.0330 0.087*
H10C 0.9416 0.3244 −0.0570 0.087*
C11 0.8891 (3) 0.0997 (2) 0.11439 (17) 0.0481 (7)
C12 0.9384 (2) 0.0273 (2) 0.05864 (17) 0.0485 (7)
H12 1.0107 0.0171 0.0784 0.058*
C13 0.9526 (3) 0.0679 (2) −0.02434 (17) 0.0510 (7)
H13A 1.0207 0.1009 −0.0273 0.061*
H13B 0.9543 0.0140 −0.0613 0.061*
C14 0.8658 (2) 0.1386 (2) −0.04903 (16) 0.0455 (7)
H14A 0.7985 0.1043 −0.0512 0.055*
H14B 0.8812 0.1630 −0.1013 0.055*
C15 0.8823 (2) −0.0758 (2) 0.06588 (17) 0.0490 (7)
C16 0.9398 (3) −0.1515 (3) 0.0156 (2) 0.0609 (9)
H16A 0.9102 −0.2149 0.0254 0.091*
H16B 1.0140 −0.1518 0.0287 0.091*
H16C 0.9315 −0.1354 −0.0390 0.091*
C17 0.7588 (2) −0.0670 (2) 0.05172 (17) 0.0438 (7)
H17 0.7446 0.0033 0.0537 0.053*
C18 0.7268 (3) −0.09720 (19) −0.03206 (16) 0.0432 (7)
H18 0.7836 −0.0755 −0.0673 0.052*
C19 0.6247 (3) −0.0503 (2) −0.06065 (16) 0.0443 (7)
C20 0.4543 (3) −0.0743 (3) −0.1149 (2) 0.0680 (10)
H20A 0.4184 −0.1222 −0.1464 0.102*
H20B 0.4677 −0.0172 −0.1460 0.102*
H20C 0.4107 −0.0572 −0.0707 0.102*
C21 0.7431 (3) −0.2402 (2) −0.1093 (2) 0.0565 (8)
C22 0.7397 (4) −0.3485 (2) −0.1083 (3) 0.0834 (13)
H22A 0.8030 −0.3738 −0.1322 0.125*
H22B 0.6787 −0.3706 −0.1371 0.125*
H22C 0.7351 −0.3709 −0.0549 0.125*
C23 0.6916 (3) −0.1102 (3) 0.12000 (18) 0.0590 (9)
C24 0.5717 (3) −0.1013 (3) 0.1041 (2) 0.0760 (11)
H24A 0.5331 −0.1158 0.1513 0.114*
H24B 0.5517 −0.1465 0.0636 0.114*
H24C 0.5556 −0.0361 0.0874 0.114*
C25 0.7149 (4) −0.2193 (3) 0.1370 (2) 0.0815 (13)
H25A 0.7901 −0.2286 0.1426 0.122*
H25B 0.6893 −0.2584 0.0941 0.122*
H25C 0.6797 −0.2385 0.1846 0.122*
C26 0.7198 (3) −0.0507 (3) 0.19481 (19) 0.0641 (9)
H26 0.6901 −0.0852 0.2402 0.077*
C27 0.8403 (3) −0.0385 (3) 0.20878 (18) 0.0599 (9)
H27 0.8563 −0.0606 0.2623 0.072*
C28 0.8853 (3) 0.0659 (3) 0.19881 (18) 0.0620 (9)
H28A 0.8418 0.1109 0.2288 0.074*
H28B 0.9566 0.0679 0.2205 0.074*
C29 0.9034 (3) −0.0992 (3) 0.1525 (2) 0.0599 (9)
C30 0.5932 (4) 0.0658 (5) 0.2431 (3) 0.0993 (16)
C31 0.5422 (5) 0.1596 (5) 0.2259 (3) 0.135 (3)
H31A 0.4720 0.1484 0.2058 0.203*
H31B 0.5833 0.1943 0.1875 0.203*
H31C 0.5379 0.1976 0.2733 0.203*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0871 (19) 0.0801 (18) 0.0570 (15) 0.0094 (16) −0.0090 (14) −0.0018 (13)
O2 0.0688 (15) 0.0690 (14) 0.0576 (14) 0.0173 (13) −0.0014 (12) −0.0152 (12)
O3 0.123 (2) 0.0782 (17) 0.0757 (18) 0.0140 (19) 0.0052 (17) −0.0303 (15)
O4 0.0820 (18) 0.0923 (19) 0.0742 (17) 0.0214 (17) −0.0234 (15) 0.0242 (16)
O5 0.0546 (13) 0.0524 (12) 0.0643 (14) −0.0015 (11) −0.0160 (12) −0.0047 (10)
O6 0.0572 (14) 0.0449 (12) 0.0844 (16) 0.0046 (10) −0.0142 (13) 0.0017 (11)
O7 0.0649 (14) 0.0394 (10) 0.0521 (12) 0.0058 (10) −0.0030 (11) 0.0013 (9)
O8 0.119 (2) 0.0714 (15) 0.0516 (15) 0.0022 (17) 0.0051 (15) −0.0070 (13)
O9 0.0713 (16) 0.103 (2) 0.0417 (12) 0.0149 (15) 0.0016 (12) −0.0055 (12)
O10 0.176 (5) 0.226 (5) 0.103 (3) 0.026 (4) 0.082 (3) 0.017 (3)
C1 0.070 (2) 0.064 (2) 0.0519 (19) −0.0011 (19) −0.0007 (18) −0.0028 (17)
C2 0.098 (3) 0.065 (2) 0.077 (3) 0.011 (2) −0.005 (3) 0.014 (2)
C3 0.093 (3) 0.0507 (19) 0.075 (3) 0.004 (2) −0.019 (2) 0.0056 (17)
C4 0.0514 (19) 0.0491 (17) 0.0555 (19) 0.0085 (15) −0.0043 (16) −0.0057 (14)
C5 0.0475 (19) 0.0506 (17) 0.0493 (17) −0.0008 (15) 0.0021 (14) −0.0059 (14)
C6 0.067 (2) 0.066 (2) 0.054 (2) −0.0016 (19) 0.0086 (18) −0.0122 (17)
C7 0.099 (3) 0.066 (2) 0.0456 (18) 0.001 (2) 0.0063 (19) −0.0097 (16)
C8 0.0516 (18) 0.0564 (18) 0.0377 (15) −0.0057 (15) 0.0005 (14) −0.0047 (14)
C9 0.0406 (16) 0.0487 (16) 0.0400 (15) −0.0035 (13) 0.0003 (13) −0.0020 (13)
C10 0.0514 (19) 0.063 (2) 0.060 (2) −0.0124 (17) −0.0019 (17) 0.0026 (17)
C11 0.0483 (18) 0.0587 (18) 0.0374 (15) −0.0050 (16) −0.0054 (14) 0.0009 (13)
C12 0.0408 (16) 0.0629 (18) 0.0419 (15) 0.0054 (15) −0.0063 (15) 0.0020 (15)
C13 0.0502 (18) 0.0547 (17) 0.0481 (17) 0.0027 (16) 0.0063 (15) 0.0004 (14)
C14 0.0504 (17) 0.0508 (16) 0.0353 (13) −0.0019 (14) 0.0025 (14) 0.0018 (13)
C15 0.0468 (17) 0.0568 (17) 0.0435 (16) 0.0072 (15) −0.0059 (14) 0.0059 (14)
C16 0.058 (2) 0.0603 (19) 0.064 (2) 0.0185 (18) −0.0057 (18) 0.0014 (17)
C17 0.0451 (17) 0.0465 (15) 0.0397 (14) 0.0014 (14) −0.0031 (13) 0.0044 (13)
C18 0.0523 (17) 0.0366 (14) 0.0407 (15) 0.0025 (14) −0.0043 (14) 0.0012 (12)
C19 0.0543 (18) 0.0414 (16) 0.0372 (14) −0.0011 (14) −0.0023 (14) 0.0008 (12)
C20 0.055 (2) 0.080 (2) 0.069 (2) 0.002 (2) −0.0195 (19) −0.0008 (19)
C21 0.056 (2) 0.0523 (18) 0.061 (2) 0.0036 (17) −0.0063 (17) −0.0084 (16)
C22 0.092 (3) 0.052 (2) 0.106 (3) 0.009 (2) 0.005 (3) −0.022 (2)
C23 0.064 (2) 0.070 (2) 0.0426 (17) −0.0084 (18) −0.0010 (16) 0.0080 (15)
C24 0.059 (2) 0.116 (3) 0.053 (2) −0.016 (2) 0.0049 (18) 0.010 (2)
C25 0.096 (3) 0.081 (3) 0.067 (2) −0.022 (2) −0.007 (2) 0.029 (2)
C26 0.067 (2) 0.086 (2) 0.0386 (17) −0.005 (2) 0.0029 (17) 0.0158 (16)
C27 0.070 (2) 0.076 (2) 0.0341 (15) 0.0009 (19) −0.0117 (16) 0.0160 (15)
C28 0.072 (2) 0.075 (2) 0.0385 (16) 0.000 (2) −0.0092 (16) 0.0015 (16)
C29 0.061 (2) 0.063 (2) 0.056 (2) 0.0001 (18) −0.0147 (17) 0.0156 (17)
C30 0.087 (3) 0.162 (5) 0.049 (2) 0.010 (4) 0.008 (2) −0.016 (3)
C31 0.100 (4) 0.208 (7) 0.099 (4) 0.070 (5) −0.027 (3) −0.056 (4)
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Geometric parameters (Å, °)

O1—C2 1.347 (5) C13—H13B 0.9700
O1—C1 1.364 (4) C14—H14A 0.9700
O2—C6 1.342 (4) C14—H14B 0.9700
O2—C5 1.463 (4) C15—C16 1.528 (5)
O3—C6 1.200 (4) C15—C29 1.531 (5)
O4—C29 1.214 (4) C15—C17 1.578 (4)
O5—C19 1.327 (3) C16—H16A 0.9600
O5—C20 1.442 (4) C16—H16B 0.9600
O6—C19 1.193 (3) C16—H16C 0.9600
O7—C21 1.348 (4) C17—C18 1.538 (4)
O7—C18 1.443 (3) C17—C23 1.554 (4)
O8—C21 1.198 (4) C17—H17 0.9800
O9—C30 1.345 (5) C18—C19 1.517 (4)
O9—C26 1.445 (5) C18—H18 0.9800
O10—C30 1.175 (7) C20—H20A 0.9600
C1—C4 1.345 (5) C20—H20B 0.9600
C1—H1 0.9300 C20—H20C 0.9600
C2—C3 1.330 (5) C21—C22 1.486 (5)
C2—H2 0.9300 C22—H22A 0.9600
C3—C4 1.423 (5) C22—H22B 0.9600
C3—H3 0.9300 C22—H22C 0.9600
C4—C5 1.494 (5) C23—C24 1.538 (5)
C5—C9 1.535 (4) C23—C26 1.552 (5)
C5—H5 0.9800 C23—C25 1.552 (5)
C6—C7 1.484 (5) C24—H24A 0.9600
C7—C8 1.514 (4) C24—H24B 0.9600
C7—H7A 0.9700 C24—H24C 0.9600
C7—H7B 0.9700 C25—H25A 0.9600
C8—C11 1.339 (4) C25—H25B 0.9600
C8—C9 1.521 (4) C25—H25C 0.9600
C9—C10 1.530 (4) C26—C27 1.544 (5)
C9—C14 1.532 (4) C26—H26 0.9800
C10—H10A 0.9600 C27—C29 1.497 (5)
C10—H10B 0.9600 C27—C28 1.549 (5)
C10—H10C 0.9600 C27—H27 0.9800
C11—C12 1.506 (4) C28—H28A 0.9700
C11—C28 1.509 (4) C28—H28B 0.9700
C12—C13 1.528 (4) C30—C31 1.467 (8)
C12—C15 1.585 (4) C31—H31A 0.9600
C12—H12 0.9800 C31—H31B 0.9600
C13—C14 1.520 (4) C31—H31C 0.9600
C13—H13A 0.9700
C2—O1—C1 105.9 (3) H16B—C16—H16C 109.5
C6—O2—C5 119.8 (3) C18—C17—C23 116.6 (3)
C19—O5—C20 116.7 (2) C18—C17—C15 112.3 (2)
C21—O7—C18 116.1 (2) C23—C17—C15 113.1 (2)
C30—O9—C26 118.8 (4) C18—C17—H17 104.5
C4—C1—O1 111.0 (3) C23—C17—H17 104.5
C4—C1—H1 124.5 C15—C17—H17 104.5
O1—C1—H1 124.5 O7—C18—C19 111.1 (2)
C3—C2—O1 111.0 (4) O7—C18—C17 110.2 (2)
C3—C2—H2 124.5 C19—C18—C17 113.9 (2)
O1—C2—H2 124.5 O7—C18—H18 107.1
C2—C3—C4 107.0 (4) C19—C18—H18 107.1
C2—C3—H3 126.5 C17—C18—H18 107.1
C4—C3—H3 126.5 O6—C19—O5 123.8 (3)
C1—C4—C3 105.1 (3) O6—C19—C18 122.4 (3)
C1—C4—C5 126.5 (3) O5—C19—C18 113.7 (2)
C3—C4—C5 128.4 (3) O5—C20—H20A 109.5
O2—C5—C4 104.2 (2) O5—C20—H20B 109.5
O2—C5—C9 111.0 (2) H20A—C20—H20B 109.5
C4—C5—C9 116.5 (3) O5—C20—H20C 109.5
O2—C5—H5 108.3 H20A—C20—H20C 109.5
C4—C5—H5 108.3 H20B—C20—H20C 109.5
C9—C5—H5 108.3 O8—C21—O7 122.5 (3)
O3—C6—O2 117.9 (3) O8—C21—C22 125.7 (3)
O3—C6—C7 122.5 (3) O7—C21—C22 111.8 (3)
O2—C6—C7 119.6 (3) C21—C22—H22A 109.5
C6—C7—C8 117.8 (3) C21—C22—H22B 109.5
C6—C7—H7A 107.8 H22A—C22—H22B 109.5
C8—C7—H7A 107.8 C21—C22—H22C 109.5
C6—C7—H7B 107.8 H22A—C22—H22C 109.5
C8—C7—H7B 107.8 H22B—C22—H22C 109.5
H7A—C7—H7B 107.2 C24—C23—C26 109.1 (3)
C11—C8—C7 121.9 (3) C24—C23—C25 107.1 (3)
C11—C8—C9 124.0 (3) C26—C23—C25 108.1 (3)
C7—C8—C9 114.0 (3) C24—C23—C17 111.9 (3)
C8—C9—C10 110.1 (2) C26—C23—C17 106.7 (3)
C8—C9—C14 110.3 (2) C25—C23—C17 113.8 (3)
C10—C9—C14 110.8 (2) C23—C24—H24A 109.5
C8—C9—C5 105.6 (2) C23—C24—H24B 109.5
C10—C9—C5 111.5 (2) H24A—C24—H24B 109.5
C14—C9—C5 108.3 (2) C23—C24—H24C 109.5
C9—C10—H10A 109.5 H24A—C24—H24C 109.5
C9—C10—H10B 109.5 H24B—C24—H24C 109.5
H10A—C10—H10B 109.5 C23—C25—H25A 109.5
C9—C10—H10C 109.5 C23—C25—H25B 109.5
H10A—C10—H10C 109.5 H25A—C25—H25B 109.5
H10B—C10—H10C 109.5 C23—C25—H25C 109.5
C8—C11—C12 123.4 (3) H25A—C25—H25C 109.5
C8—C11—C28 122.3 (3) H25B—C25—H25C 109.5
C12—C11—C28 114.2 (3) O9—C26—C27 110.4 (3)
C11—C12—C13 112.9 (3) O9—C26—C23 108.8 (3)
C11—C12—C15 110.8 (2) C27—C26—C23 114.1 (3)
C13—C12—C15 116.7 (3) O9—C26—H26 107.8
C11—C12—H12 105.1 C27—C26—H26 107.8
C13—C12—H12 105.1 C23—C26—H26 107.8
C15—C12—H12 105.1 C29—C27—C26 111.3 (3)
C14—C13—C12 113.8 (3) C29—C27—C28 104.4 (3)
C14—C13—H13A 108.8 C26—C27—C28 116.3 (3)
C12—C13—H13A 108.8 C29—C27—H27 108.2
C14—C13—H13B 108.8 C26—C27—H27 108.2
C12—C13—H13B 108.8 C28—C27—H27 108.2
H13A—C13—H13B 107.7 C11—C28—C27 113.5 (3)
C13—C14—C9 111.9 (2) C11—C28—H28A 108.9
C13—C14—H14A 109.2 C27—C28—H28A 108.9
C9—C14—H14A 109.2 C11—C28—H28B 108.9
C13—C14—H14B 109.2 C27—C28—H28B 108.9
C9—C14—H14B 109.2 H28A—C28—H28B 107.7
H14A—C14—H14B 107.9 O4—C29—C27 122.3 (3)
C16—C15—C29 108.3 (3) O4—C29—C15 123.0 (3)
C16—C15—C17 115.7 (3) C27—C29—C15 114.0 (3)
C29—C15—C17 109.6 (3) O10—C30—O9 121.8 (6)
C16—C15—C12 110.5 (3) O10—C30—C31 126.1 (5)
C29—C15—C12 100.6 (3) O9—C30—C31 112.1 (5)
C17—C15—C12 111.0 (2) C30—C31—H31A 109.5
C15—C16—H16A 109.5 C30—C31—H31B 109.5
C15—C16—H16B 109.5 H31A—C31—H31B 109.5
H16A—C16—H16B 109.5 C30—C31—H31C 109.5
C15—C16—H16C 109.5 H31A—C31—H31C 109.5
H16A—C16—H16C 109.5 H31B—C31—H31C 109.5
C2—O1—C1—C4 0.0 (4) C12—C15—C17—C18 100.0 (3)
C1—O1—C2—C3 0.0 (5) C16—C15—C17—C23 107.4 (3)
O1—C2—C3—C4 0.0 (5) C29—C15—C17—C23 −15.4 (4)
O1—C1—C4—C3 0.0 (4) C12—C15—C17—C23 −125.6 (3)
O1—C1—C4—C5 179.0 (3) C21—O7—C18—C19 82.4 (3)
C2—C3—C4—C1 0.0 (4) C21—O7—C18—C17 −150.4 (3)
C2—C3—C4—C5 −179.0 (3) C23—C17—C18—O7 −52.8 (3)
C6—O2—C5—C4 −166.2 (3) C15—C17—C18—O7 80.0 (3)
C6—O2—C5—C9 −40.0 (4) C23—C17—C18—C19 72.9 (3)
C1—C4—C5—O2 −134.2 (3) C15—C17—C18—C19 −154.4 (2)
C3—C4—C5—O2 44.6 (4) C20—O5—C19—O6 −2.2 (4)
C1—C4—C5—C9 103.2 (4) C20—O5—C19—C18 179.5 (3)
C3—C4—C5—C9 −78.0 (4) O7—C18—C19—O6 179.6 (3)
C5—O2—C6—O3 178.5 (3) C17—C18—C19—O6 54.4 (4)
C5—O2—C6—C7 −2.7 (5) O7—C18—C19—O5 −2.1 (3)
O3—C6—C7—C8 −162.5 (4) C17—C18—C19—O5 −127.3 (3)
O2—C6—C7—C8 18.8 (5) C18—O7—C21—O8 −1.8 (5)
C6—C7—C8—C11 −171.5 (3) C18—O7—C21—C22 177.7 (3)
C6—C7—C8—C9 9.4 (5) C18—C17—C23—C24 −47.1 (4)
C11—C8—C9—C10 −106.3 (3) C15—C17—C23—C24 −179.4 (3)
C7—C8—C9—C10 72.8 (4) C18—C17—C23—C26 −166.3 (3)
C11—C8—C9—C14 16.4 (4) C15—C17—C23—C26 61.3 (4)
C7—C8—C9—C14 −164.5 (3) C18—C17—C23—C25 74.5 (4)
C11—C8—C9—C5 133.3 (3) C15—C17—C23—C25 −57.9 (4)
C7—C8—C9—C5 −47.7 (3) C30—O9—C26—C27 −119.0 (4)
O2—C5—C9—C8 63.6 (3) C30—O9—C26—C23 115.2 (4)
C4—C5—C9—C8 −177.4 (3) C24—C23—C26—O9 −45.9 (4)
O2—C5—C9—C10 −55.9 (3) C25—C23—C26—O9 −162.1 (3)
C4—C5—C9—C10 63.0 (3) C17—C23—C26—O9 75.1 (3)
O2—C5—C9—C14 −178.1 (2) C24—C23—C26—C27 −169.6 (3)
C4—C5—C9—C14 −59.2 (3) C25—C23—C26—C27 74.2 (4)
C7—C8—C11—C12 −173.2 (3) C17—C23—C26—C27 −48.6 (4)
C9—C8—C11—C12 5.9 (5) O9—C26—C27—C29 −130.9 (3)
C7—C8—C11—C28 2.8 (5) C23—C26—C27—C29 −8.0 (4)
C9—C8—C11—C28 −178.1 (3) O9—C26—C27—C28 −11.4 (4)
C8—C11—C12—C13 2.8 (4) C23—C26—C27—C28 111.4 (4)
C28—C11—C12—C13 −173.5 (3) C8—C11—C28—C27 135.0 (3)
C8—C11—C12—C15 −130.2 (3) C12—C11—C28—C27 −48.6 (4)
C28—C11—C12—C15 53.5 (3) C29—C27—C28—C11 51.4 (4)
C11—C12—C13—C14 −33.9 (4) C26—C27—C28—C11 −71.7 (4)
C15—C12—C13—C14 96.2 (3) C26—C27—C29—O4 −130.9 (4)
C12—C13—C14—C9 57.0 (3) C28—C27—C29—O4 102.9 (4)
C8—C9—C14—C13 −46.3 (3) C26—C27—C29—C15 58.6 (4)
C10—C9—C14—C13 76.0 (3) C28—C27—C29—C15 −67.7 (4)
C5—C9—C14—C13 −161.5 (2) C16—C15—C29—O4 17.0 (5)
C11—C12—C15—C16 −174.1 (2) C17—C15—C29—O4 144.1 (3)
C13—C12—C15—C16 54.8 (3) C12—C15—C29—O4 −98.9 (4)
C11—C12—C15—C29 −59.9 (3) C16—C15—C29—C27 −172.5 (3)
C13—C12—C15—C29 169.0 (3) C17—C15—C29—C27 −45.4 (4)
C11—C12—C15—C17 56.0 (3) C12—C15—C29—C27 71.6 (3)
C13—C12—C15—C17 −75.1 (3) C26—O9—C30—O10 4.9 (7)
C16—C15—C17—C18 −27.1 (4) C26—O9—C30—C31 −174.6 (4)
C29—C15—C17—C18 −149.8 (3)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5263).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017733/bt5263sup1.cif

e-66-o1396-sup1.cif (27.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017733/bt5263Isup2.hkl

e-66-o1396-Isup2.hkl (184.9KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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