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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1396.
Published online 2010 May 22. doi:  10.1107/S1600536810017733
PMCID: PMC2979530

Swietenolide diacetate from the seeds of Swietenia macrophylla

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 [triangle]); Connolly & Labbe (1980 [triangle]); Connolly et al. (1965 [triangle]); Govindachari et al. (1999 [triangle]); Kadota, Marpaung et al. (1990 [triangle]); Kadota, Yanagawa et al. (1990 [triangle]); Mootoo et al. (1999 [triangle]); Narender et al. (2008 [triangle]); Schefer et al. (2006 [triangle]); Taylor & Taylor (1983 [triangle]); Yuan et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1396-scheme1.jpg

Experimental

Crystal data

  • C31H38O10
  • M r = 570.61
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1396-efi1.jpg
  • 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 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017733/bt5263Isup2.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.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C31H38O10 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

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

Bruker SMART APEX diffractometer2491 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.077
graphiteθmax = 27.5°, θmin = 1.9°
ω scansh = −14→16
28065 measured reflectionsk = −17→17
3771 independent reflectionsl = −21→22

Refinement

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 = 1.02w = 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

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

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)
H10.62690.2091−0.13250.074*
C20.7183 (4)0.4023 (3)−0.1918 (2)0.0801 (12)
H20.72960.4527−0.22740.096*
C30.7605 (4)0.3985 (3)−0.1201 (2)0.0729 (11)
H30.80530.4445−0.09750.087*
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*
H10C0.94160.3244−0.05700.087*
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)
H13A1.02070.1009−0.02730.061*
H13B0.95430.0140−0.06130.061*
C140.8658 (2)0.1386 (2)−0.04903 (16)0.0455 (7)
H14A0.79850.1043−0.05120.055*
H14B0.88120.1630−0.10130.055*
C150.8823 (2)−0.0758 (2)0.06588 (17)0.0490 (7)
C160.9398 (3)−0.1515 (3)0.0156 (2)0.0609 (9)
H16A0.9102−0.21490.02540.091*
H16B1.0140−0.15180.02870.091*
H16C0.9315−0.1354−0.03900.091*
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)
H180.7836−0.0755−0.06730.052*
C190.6247 (3)−0.0503 (2)−0.06065 (16)0.0443 (7)
C200.4543 (3)−0.0743 (3)−0.1149 (2)0.0680 (10)
H20A0.4184−0.1222−0.14640.102*
H20B0.4677−0.0172−0.14600.102*
H20C0.4107−0.0572−0.07070.102*
C210.7431 (3)−0.2402 (2)−0.1093 (2)0.0565 (8)
C220.7397 (4)−0.3485 (2)−0.1083 (3)0.0834 (13)
H22A0.8030−0.3738−0.13220.125*
H22B0.6787−0.3706−0.13710.125*
H22C0.7351−0.3709−0.05490.125*
C230.6916 (3)−0.1102 (3)0.12000 (18)0.0590 (9)
C240.5717 (3)−0.1013 (3)0.1041 (2)0.0760 (11)
H24A0.5331−0.11580.15130.114*
H24B0.5517−0.14650.06360.114*
H24C0.5556−0.03610.08740.114*
C250.7149 (4)−0.2193 (3)0.1370 (2)0.0815 (13)
H25A0.7901−0.22860.14260.122*
H25B0.6893−0.25840.09410.122*
H25C0.6797−0.23850.18460.122*
C260.7198 (3)−0.0507 (3)0.19481 (19)0.0641 (9)
H260.6901−0.08520.24020.077*
C270.8403 (3)−0.0385 (3)0.20878 (18)0.0599 (9)
H270.8563−0.06060.26230.072*
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)

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, °)

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—C23−15.4 (4)
O1—C1—C4—C30.0 (4)C12—C15—C17—C23−125.6 (3)
O1—C1—C4—C5179.0 (3)C21—O7—C18—C1982.4 (3)
C2—C3—C4—C10.0 (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—O780.0 (3)
C6—O2—C5—C9−40.0 (4)C23—C17—C18—C1972.9 (3)
C1—C4—C5—O2−134.2 (3)C15—C17—C18—C19−154.4 (2)
C3—C4—C5—O244.6 (4)C20—O5—C19—O6−2.2 (4)
C1—C4—C5—C9103.2 (4)C20—O5—C19—C18179.5 (3)
C3—C4—C5—C9−78.0 (4)O7—C18—C19—O6179.6 (3)
C5—O2—C6—O3178.5 (3)C17—C18—C19—O654.4 (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—C818.8 (5)C18—O7—C21—O8−1.8 (5)
C6—C7—C8—C11−171.5 (3)C18—O7—C21—C22177.7 (3)
C6—C7—C8—C99.4 (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—C1072.8 (4)C18—C17—C23—C26−166.3 (3)
C11—C8—C9—C1416.4 (4)C15—C17—C23—C2661.3 (4)
C7—C8—C9—C14−164.5 (3)C18—C17—C23—C2574.5 (4)
C11—C8—C9—C5133.3 (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—C863.6 (3)C30—O9—C26—C23115.2 (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—C1063.0 (3)C17—C23—C26—O975.1 (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—C2774.2 (4)
C7—C8—C11—C12−173.2 (3)C17—C23—C26—C27−48.6 (4)
C9—C8—C11—C125.9 (5)O9—C26—C27—C29−130.9 (3)
C7—C8—C11—C282.8 (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—C132.8 (4)C23—C26—C27—C28111.4 (4)
C28—C11—C12—C13−173.5 (3)C8—C11—C28—C27135.0 (3)
C8—C11—C12—C15−130.2 (3)C12—C11—C28—C27−48.6 (4)
C28—C11—C12—C1553.5 (3)C29—C27—C28—C1151.4 (4)
C11—C12—C13—C14−33.9 (4)C26—C27—C28—C11−71.7 (4)
C15—C12—C13—C1496.2 (3)C26—C27—C29—O4−130.9 (4)
C12—C13—C14—C957.0 (3)C28—C27—C29—O4102.9 (4)
C8—C9—C14—C13−46.3 (3)C26—C27—C29—C1558.6 (4)
C10—C9—C14—C1376.0 (3)C28—C27—C29—C15−67.7 (4)
C5—C9—C14—C13−161.5 (2)C16—C15—C29—O417.0 (5)
C11—C12—C15—C16−174.1 (2)C17—C15—C29—O4144.1 (3)
C13—C12—C15—C1654.8 (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—C29169.0 (3)C17—C15—C29—C27−45.4 (4)
C11—C12—C15—C1756.0 (3)C12—C15—C29—C2771.6 (3)
C13—C12—C15—C17−75.1 (3)C26—O9—C30—O104.9 (7)
C16—C15—C17—C18−27.1 (4)C26—O9—C30—C31−174.6 (4)
C29—C15—C17—C18−149.8 (3)

Footnotes

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

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