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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1621.
Published online 2010 June 9. doi:  10.1107/S1600536810021136
PMCID: PMC3006935

14-Hy­droxy-8,14-secogammacera-7-ene-3,21-dione from the bark of Lansium domesticum Corr.

Abstract

In the title compound (kokosanolide B), C30H48O3, the hexa­hydro- and octa­hydro­naphthalen-2-one ring systems are connected through an ethyl­ene fragment, with a C—CH2—CH2—C torsion angle of 176.2 (2)°. The cyclo­hexene ring adopts a half-chair conformation, while the other six-membered rings adopt distorted chair conformations. In the crystal, adjacent mol­ecules are linked into a zigzag chain along the b axis by O—H(...)O hydrogen bonds involving the hy­droxy and carbonyl groups.

Related literature

For a related compound from the same species, see: Tjokronegero et al. (2009 [triangle]). For kokosanolide A, see: Mayanti et al. (2009 [triangle]).

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Object name is e-66-o1621-scheme1.jpg

Experimental

Crystal data

  • C30H48O3
  • M r = 456.68
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1621-efi1.jpg
  • a = 11.8841 (11) Å
  • b = 14.8301 (13) Å
  • c = 15.2755 (13) Å
  • V = 2692.2 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 100 K
  • 0.20 × 0.10 × 0.05 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • 26171 measured reflections
  • 3469 independent reflections
  • 3033 reflections with I > 2σ(I)
  • R int = 0.067

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.098
  • S = 1.01
  • 3469 reflections
  • 310 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.20 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]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021136/ci5095sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021136/ci5095Isup2.hkl

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

Acknowledgments

This work was supported by the Directorate of Higher Education, Indonesia, the University of Padjadjaran (I-MHERE Project) and the University of Malaya (UMRG RG011/09BIO).

supplementary crystallographic information

Comment

A previous study on the bark of Lansium domesticum Corr (Meliaceae) yielded a co-crystal, 8,14-secogammacera-7,14 (27)-diene–3,21-dione-8,14-secogammacera-7,14-diene-3,21-dione (1.5/0.5). The major component has an excocyclic double bond and an endocyclic double bond (Tjokronegero et al., 2009). In the present compound (Scheme I), a molecule of water has been added across the endocyclic double bond to furnish the corresponding alcohol (Fig. 1).

The hexahydro-naphthalen-2-one and octahydro-naphthalen-2-one ring systems are connected through an ethylene fragment, with a C–CH2–CH2–C torsion angle of 176.2 (2)°. The hydroxy unit of one fused-ring forms a hydrogen bond to the ketonic unit of the other fused-ring of an adjacent molecule to generate a zigzag chain.

Experimental

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 bark of L. domesticum (3 kg) was extracted exhaustively by methanol at room temperature. The methanol extract (250 g) was partitioned between n-hexane and ethyl acetate to give an n-hexane soluble fraction (70 g) and an ethyl acetate soluble fraction (40 g). The ethyl acetate fraction was subjected to vacuum column chromatography on silica gel 60 by using a step gradient of n-hexane/ethyl acetate/methanol. The fraction eluted by n-hexane/ethyl acetate (80:20) was further separated by column chromatography on silica gel n-hexane/ethyl acetate (95:5) and n-hexane/acetone (90:10). Single crystals were obtained by slow evaporation of the solvent.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C—H = 0.95–1.00 Å] and were included in the refinement in the riding-model approximation, with Uiso(H) = 1.2–1.5U(C). The hydroxy H-atom was located in a difference Fourier map and was refined with a distance restraint of O–H = 0.84 (1) Å; its Uiso parameter was freely refined. 2721 Friedel pairs were merged

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of C30H48O3 at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.

Crystal data

C30H48O3F(000) = 1008
Mr = 456.68Dx = 1.127 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3379 reflections
a = 11.8841 (11) Åθ = 2.6–20.6°
b = 14.8301 (13) ŵ = 0.07 mm1
c = 15.2755 (13) ÅT = 100 K
V = 2692.2 (4) Å3Plate, colourless
Z = 40.20 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEXII diffractometer3033 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.067
graphiteθmax = 27.5°, θmin = 1.9°
ω scansh = −15→15
26171 measured reflectionsk = −17→19
3469 independent reflectionsl = −19→19

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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0534P)2 + 0.4471P] where P = (Fo2 + 2Fc2)/3
3469 reflections(Δ/σ)max = 0.001
310 parametersΔρmax = 0.25 e Å3
1 restraintΔρmin = −0.20 e Å3

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

xyzUiso*/Ueq
O10.85660 (14)0.46079 (11)1.07799 (11)0.0313 (4)
O20.92757 (12)0.95328 (10)1.00483 (10)0.0193 (3)
H20.956 (2)0.9990 (13)1.0283 (17)0.044 (9)*
O30.97661 (13)0.62965 (10)0.44013 (10)0.0230 (3)
C11.00012 (16)0.70418 (13)0.99742 (13)0.0139 (4)
C20.94385 (17)0.63545 (13)0.93607 (13)0.0171 (4)
H2A0.86270.64970.93150.021*
H2B0.97700.64140.87690.021*
C30.95721 (19)0.53755 (14)0.96705 (14)0.0205 (5)
H3A0.91410.49740.92760.025*
H3B1.03750.52020.96320.025*
C40.91696 (17)0.52388 (14)1.05964 (15)0.0190 (4)
C50.95844 (18)0.59017 (14)1.12907 (14)0.0188 (4)
C60.95358 (17)0.68799 (13)1.09158 (13)0.0155 (4)
H60.87140.70171.08700.019*
C71.07759 (19)0.55946 (15)1.15649 (15)0.0234 (5)
H7A1.07350.49901.18220.035*
H7B1.10810.60171.19970.035*
H7C1.12670.55821.10490.035*
C80.8817 (2)0.58287 (17)1.20997 (15)0.0296 (5)
H8A0.87240.51931.22590.044*
H8B0.80800.60911.19650.044*
H8C0.91580.61561.25900.044*
C91.12928 (17)0.69324 (14)0.98960 (14)0.0185 (4)
H9A1.14780.62930.98200.028*
H9B1.16530.71601.04290.028*
H9C1.15650.72750.93900.028*
C100.99922 (19)0.75933 (14)1.15478 (13)0.0199 (4)
H10A0.97210.74651.21480.024*
H10B1.08250.75711.15530.024*
C110.96049 (19)0.85294 (14)1.12704 (14)0.0204 (4)
H11A0.99250.89801.16790.025*
H11B0.87750.85611.13180.025*
C120.99487 (18)0.87777 (13)1.03345 (13)0.0162 (4)
C130.96039 (16)0.80090 (13)0.97016 (12)0.0133 (4)
H130.87650.79830.97490.016*
C141.11914 (18)0.90456 (14)1.03022 (15)0.0212 (5)
H14A1.14280.91100.96910.032*
H14B1.16450.85781.05870.032*
H14C1.12960.96201.06080.032*
C150.98231 (16)0.82616 (14)0.87297 (13)0.0160 (4)
H15A1.00860.88940.86980.019*
H15B1.04280.78720.84950.019*
C160.87697 (17)0.81557 (14)0.81600 (13)0.0159 (4)
H16A0.81520.85110.84250.019*
H16B0.85390.75140.81660.019*
C170.89186 (16)0.84596 (14)0.71915 (12)0.0152 (4)
H170.97470.85200.70920.018*
C180.84100 (17)0.93890 (14)0.70231 (13)0.0168 (4)
C190.78520 (18)0.95775 (14)0.62919 (14)0.0184 (4)
H190.75111.01550.62450.022*
C200.77245 (18)0.89399 (14)0.55361 (13)0.0178 (4)
H20A0.78460.92700.49810.021*
H20B0.69500.86940.55300.021*
C210.85675 (16)0.81635 (13)0.56021 (13)0.0138 (4)
H210.93250.84560.55790.017*
C220.84927 (16)0.77380 (13)0.65296 (13)0.0133 (4)
C230.8624 (2)1.01122 (15)0.76957 (15)0.0237 (5)
H23A0.82261.06640.75270.036*
H23B0.94341.02340.77290.036*
H23C0.83530.99090.82680.036*
C240.72842 (17)0.74445 (14)0.67586 (13)0.0165 (4)
H24A0.72860.71260.73210.025*
H24B0.69980.70430.63000.025*
H24C0.68010.79780.68010.025*
C250.92925 (17)0.69270 (14)0.65756 (13)0.0171 (4)
H25A1.00770.71430.65210.021*
H25B0.92140.66350.71550.021*
C260.90659 (19)0.62292 (14)0.58610 (13)0.0194 (4)
H26A0.96020.57220.59220.023*
H26B0.82950.59870.59290.023*
C270.91895 (17)0.66457 (14)0.49686 (13)0.0166 (4)
C280.85347 (18)0.75171 (14)0.47911 (12)0.0163 (4)
C290.73416 (19)0.72086 (16)0.45128 (14)0.0226 (5)
H29A0.73910.68590.39700.034*
H29B0.68650.77390.44180.034*
H29C0.70140.68330.49750.034*
C300.9062 (2)0.80059 (15)0.40058 (14)0.0240 (5)
H30A0.90830.75980.35010.036*
H30B0.98300.81930.41540.036*
H30C0.86110.85380.38610.036*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0368 (9)0.0232 (9)0.0339 (10)−0.0136 (8)−0.0019 (8)0.0039 (7)
O20.0229 (8)0.0134 (7)0.0215 (8)0.0024 (6)−0.0014 (6)−0.0003 (6)
O30.0264 (8)0.0221 (8)0.0205 (8)0.0031 (7)0.0032 (7)−0.0024 (7)
C10.0152 (9)0.0139 (10)0.0125 (9)−0.0004 (8)0.0005 (8)−0.0016 (8)
C20.0207 (9)0.0159 (10)0.0148 (10)−0.0006 (8)−0.0008 (8)−0.0018 (8)
C30.0266 (11)0.0153 (10)0.0195 (10)−0.0006 (9)−0.0009 (9)−0.0049 (8)
C40.0173 (9)0.0163 (10)0.0234 (11)0.0010 (8)−0.0042 (9)0.0012 (9)
C50.0233 (11)0.0160 (10)0.0171 (10)0.0011 (8)0.0001 (9)0.0032 (8)
C60.0175 (9)0.0147 (9)0.0142 (9)0.0007 (8)−0.0008 (8)0.0004 (8)
C70.0302 (11)0.0168 (10)0.0232 (11)0.0001 (10)−0.0095 (10)0.0006 (9)
C80.0416 (14)0.0241 (12)0.0230 (12)−0.0026 (11)0.0101 (11)0.0047 (10)
C90.0168 (9)0.0185 (10)0.0203 (10)0.0013 (8)−0.0009 (8)−0.0004 (9)
C100.0282 (11)0.0168 (10)0.0146 (10)−0.0029 (9)−0.0019 (9)−0.0017 (8)
C110.0296 (11)0.0157 (10)0.0160 (10)0.0018 (9)0.0005 (9)−0.0032 (8)
C120.0198 (10)0.0129 (10)0.0159 (10)0.0022 (8)−0.0011 (8)−0.0004 (8)
C130.0138 (9)0.0137 (10)0.0124 (9)−0.0008 (8)−0.0008 (7)−0.0006 (8)
C140.0209 (10)0.0169 (10)0.0257 (11)−0.0029 (8)−0.0066 (9)−0.0010 (9)
C150.0152 (9)0.0181 (10)0.0146 (10)−0.0016 (8)0.0006 (8)0.0010 (8)
C160.0172 (9)0.0155 (10)0.0149 (9)−0.0016 (8)−0.0004 (8)0.0004 (8)
C170.0159 (9)0.0158 (10)0.0139 (9)−0.0008 (8)−0.0003 (8)0.0015 (8)
C180.0189 (9)0.0133 (10)0.0182 (10)−0.0013 (8)0.0041 (8)−0.0009 (8)
C190.0211 (10)0.0134 (10)0.0208 (11)0.0027 (8)0.0032 (8)−0.0002 (8)
C200.0224 (10)0.0163 (10)0.0146 (10)0.0029 (8)−0.0013 (8)−0.0003 (8)
C210.0151 (9)0.0136 (10)0.0128 (9)−0.0013 (8)0.0005 (8)0.0002 (8)
C220.0135 (9)0.0124 (9)0.0140 (9)−0.0002 (7)−0.0005 (8)0.0003 (8)
C230.0336 (12)0.0156 (11)0.0220 (11)−0.0013 (9)−0.0010 (10)−0.0029 (9)
C240.0182 (9)0.0184 (10)0.0129 (9)−0.0033 (8)0.0015 (8)0.0001 (8)
C250.0198 (10)0.0181 (10)0.0134 (9)0.0022 (8)−0.0005 (8)0.0009 (8)
C260.0264 (11)0.0133 (10)0.0187 (11)0.0031 (9)0.0011 (9)0.0011 (8)
C270.0182 (9)0.0150 (10)0.0166 (10)−0.0030 (8)0.0001 (8)−0.0031 (8)
C280.0198 (10)0.0161 (10)0.0130 (10)−0.0006 (8)0.0009 (8)−0.0001 (8)
C290.0249 (11)0.0232 (11)0.0195 (11)−0.0003 (9)−0.0051 (9)−0.0027 (9)
C300.0366 (12)0.0191 (11)0.0164 (10)−0.0002 (10)0.0065 (9)0.0010 (9)

Geometric parameters (Å, °)

O1—C41.212 (3)C15—C161.533 (3)
O2—C121.444 (2)C15—H15A0.99
O2—H20.841 (10)C15—H15B0.99
O3—C271.220 (2)C16—C171.557 (3)
C1—C21.538 (3)C16—H16A0.99
C1—C91.548 (3)C16—H16B0.99
C1—C61.560 (3)C17—C181.527 (3)
C1—C131.566 (3)C17—C221.557 (3)
C2—C31.535 (3)C17—H171.00
C2—H2A0.99C18—C191.329 (3)
C2—H2B0.99C18—C231.507 (3)
C3—C41.507 (3)C19—C201.500 (3)
C3—H3A0.99C19—H190.95
C3—H3B0.99C20—C211.530 (3)
C4—C51.528 (3)C20—H20A0.99
C5—C81.540 (3)C20—H20B0.99
C5—C71.545 (3)C21—C221.553 (3)
C5—C61.561 (3)C21—C281.567 (3)
C6—C101.531 (3)C21—H211.00
C6—H61.00C22—C251.535 (3)
C7—H7A0.98C22—C241.541 (3)
C7—H7B0.98C23—H23A0.98
C7—H7C0.98C23—H23B0.98
C8—H8A0.98C23—H23C0.98
C8—H8B0.98C24—H24A0.98
C8—H8C0.98C24—H24B0.98
C9—H9A0.98C24—H24C0.98
C9—H9B0.98C25—C261.528 (3)
C9—H9C0.98C25—H25A0.99
C10—C111.523 (3)C25—H25B0.99
C10—H10A0.99C26—C271.504 (3)
C10—H10B0.99C26—H26A0.99
C11—C121.532 (3)C26—H26B0.99
C11—H11A0.99C27—C281.533 (3)
C11—H11B0.99C28—C301.535 (3)
C12—C141.530 (3)C28—C291.549 (3)
C12—C131.550 (3)C29—H29A0.98
C13—C151.553 (3)C29—H29B0.98
C13—H131.00C29—H29C0.98
C14—H14A0.98C30—H30A0.98
C14—H14B0.98C30—H30B0.98
C14—H14C0.98C30—H30C0.98
C12—O2—H2106 (2)C16—C15—H15B109.1
C2—C1—C9108.35 (16)C13—C15—H15B109.1
C2—C1—C6107.81 (16)H15A—C15—H15B107.9
C9—C1—C6113.99 (17)C15—C16—C17114.65 (16)
C2—C1—C13108.29 (16)C15—C16—H16A108.6
C9—C1—C13111.98 (16)C17—C16—H16A108.6
C6—C1—C13106.21 (15)C15—C16—H16B108.6
C3—C2—C1113.21 (17)C17—C16—H16B108.6
C3—C2—H2A108.9H16A—C16—H16B107.6
C1—C2—H2A108.9C18—C17—C22112.49 (16)
C3—C2—H2B108.9C18—C17—C16112.11 (16)
C1—C2—H2B108.9C22—C17—C16112.41 (16)
H2A—C2—H2B107.8C18—C17—H17106.4
C4—C3—C2112.56 (18)C22—C17—H17106.4
C4—C3—H3A109.1C16—C17—H17106.4
C2—C3—H3A109.1C19—C18—C23120.51 (19)
C4—C3—H3B109.1C19—C18—C17121.94 (19)
C2—C3—H3B109.1C23—C18—C17117.44 (18)
H3A—C3—H3B107.8C18—C19—C20124.39 (19)
O1—C4—C3120.6 (2)C18—C19—H19117.8
O1—C4—C5121.8 (2)C20—C19—H19117.8
C3—C4—C5117.56 (18)C19—C20—C21110.95 (17)
C4—C5—C8108.71 (18)C19—C20—H20A109.4
C4—C5—C7107.11 (17)C21—C20—H20A109.4
C8—C5—C7107.74 (18)C19—C20—H20B109.4
C4—C5—C6109.35 (17)C21—C20—H20B109.4
C8—C5—C6109.75 (18)H20A—C20—H20B108.0
C7—C5—C6114.03 (18)C20—C21—C22109.17 (16)
C10—C6—C1110.45 (16)C20—C21—C28113.08 (16)
C10—C6—C5113.44 (17)C22—C21—C28118.11 (16)
C1—C6—C5117.93 (17)C20—C21—H21105.1
C10—C6—H6104.5C22—C21—H21105.1
C1—C6—H6104.5C28—C21—H21105.1
C5—C6—H6104.5C25—C22—C24110.21 (16)
C5—C7—H7A109.5C25—C22—C21108.94 (16)
C5—C7—H7B109.5C24—C22—C21112.03 (16)
H7A—C7—H7B109.5C25—C22—C17107.92 (16)
C5—C7—H7C109.5C24—C22—C17110.47 (16)
H7A—C7—H7C109.5C21—C22—C17107.13 (15)
H7B—C7—H7C109.5C18—C23—H23A109.5
C5—C8—H8A109.5C18—C23—H23B109.5
C5—C8—H8B109.5H23A—C23—H23B109.5
H8A—C8—H8B109.5C18—C23—H23C109.5
C5—C8—H8C109.5H23A—C23—H23C109.5
H8A—C8—H8C109.5H23B—C23—H23C109.5
H8B—C8—H8C109.5C22—C24—H24A109.5
C1—C9—H9A109.5C22—C24—H24B109.5
C1—C9—H9B109.5H24A—C24—H24B109.5
H9A—C9—H9B109.5C22—C24—H24C109.5
C1—C9—H9C109.5H24A—C24—H24C109.5
H9A—C9—H9C109.5H24B—C24—H24C109.5
H9B—C9—H9C109.5C26—C25—C22112.89 (16)
C11—C10—C6110.33 (17)C26—C25—H25A109.0
C11—C10—H10A109.6C22—C25—H25A109.0
C6—C10—H10A109.6C26—C25—H25B109.0
C11—C10—H10B109.6C22—C25—H25B109.0
C6—C10—H10B109.6H25A—C25—H25B107.8
H10A—C10—H10B108.1C27—C26—C25110.62 (16)
C10—C11—C12113.46 (17)C27—C26—H26A109.5
C10—C11—H11A108.9C25—C26—H26A109.5
C12—C11—H11A108.9C27—C26—H26B109.5
C10—C11—H11B108.9C25—C26—H26B109.5
C12—C11—H11B108.9H26A—C26—H26B108.1
H11A—C11—H11B107.7O3—C27—C26121.62 (19)
O2—C12—C14108.86 (16)O3—C27—C28121.16 (18)
O2—C12—C11108.74 (17)C26—C27—C28117.20 (17)
C14—C12—C11110.49 (18)C27—C28—C30109.20 (17)
O2—C12—C13103.60 (15)C27—C28—C29105.32 (17)
C14—C12—C13115.21 (17)C30—C28—C29107.38 (17)
C11—C12—C13109.57 (16)C27—C28—C21111.30 (16)
C12—C13—C15112.00 (16)C30—C28—C21108.59 (16)
C12—C13—C1115.34 (16)C29—C28—C21114.86 (17)
C15—C13—C1115.11 (16)C28—C29—H29A109.5
C12—C13—H13104.2C28—C29—H29B109.5
C15—C13—H13104.2H29A—C29—H29B109.5
C1—C13—H13104.2C28—C29—H29C109.5
C12—C14—H14A109.5H29A—C29—H29C109.5
C12—C14—H14B109.5H29B—C29—H29C109.5
H14A—C14—H14B109.5C28—C30—H30A109.5
C12—C14—H14C109.5C28—C30—H30B109.5
H14A—C14—H14C109.5H30A—C30—H30B109.5
H14B—C14—H14C109.5C28—C30—H30C109.5
C16—C15—C13112.40 (16)H30A—C30—H30C109.5
C16—C15—H15A109.1H30B—C30—H30C109.5
C13—C15—H15A109.1
C9—C1—C2—C369.8 (2)C1—C13—C15—C1699.7 (2)
C6—C1—C2—C3−54.1 (2)C13—C15—C16—C17176.18 (17)
C13—C1—C2—C3−168.58 (17)C15—C16—C17—C18−101.6 (2)
C1—C2—C3—C454.2 (2)C15—C16—C17—C22130.50 (18)
C2—C3—C4—O1133.3 (2)C22—C17—C18—C19−12.3 (3)
C2—C3—C4—C5−48.9 (3)C16—C17—C18—C19−140.2 (2)
O1—C4—C5—C8−19.3 (3)C22—C17—C18—C23171.38 (17)
C3—C4—C5—C8162.88 (19)C16—C17—C18—C2343.5 (2)
O1—C4—C5—C796.9 (2)C23—C18—C19—C20171.8 (2)
C3—C4—C5—C7−81.0 (2)C17—C18—C19—C20−4.3 (3)
O1—C4—C5—C6−139.1 (2)C18—C19—C20—C21−15.5 (3)
C3—C4—C5—C643.1 (2)C19—C20—C21—C2250.8 (2)
C2—C1—C6—C10−175.45 (16)C19—C20—C21—C28−175.54 (17)
C9—C1—C6—C1064.2 (2)C20—C21—C22—C25176.90 (16)
C13—C1—C6—C10−59.6 (2)C28—C21—C22—C2545.9 (2)
C2—C1—C6—C551.8 (2)C20—C21—C22—C2454.7 (2)
C9—C1—C6—C5−68.5 (2)C28—C21—C22—C24−76.3 (2)
C13—C1—C6—C5167.74 (17)C20—C21—C22—C17−66.60 (19)
C4—C5—C6—C10−177.08 (17)C28—C21—C22—C17162.38 (16)
C8—C5—C6—C1063.8 (2)C18—C17—C22—C25163.45 (16)
C7—C5—C6—C10−57.2 (2)C16—C17—C22—C25−68.9 (2)
C4—C5—C6—C1−45.7 (2)C18—C17—C22—C24−76.0 (2)
C8—C5—C6—C1−164.88 (18)C16—C17—C22—C2451.7 (2)
C7—C5—C6—C174.2 (2)C18—C17—C22—C2146.3 (2)
C1—C6—C10—C1162.1 (2)C16—C17—C22—C21173.97 (15)
C5—C6—C10—C11−162.95 (18)C24—C22—C25—C2667.7 (2)
C6—C10—C11—C12−57.2 (2)C21—C22—C25—C26−55.6 (2)
C10—C11—C12—O2163.03 (17)C17—C22—C25—C26−171.57 (16)
C10—C11—C12—C14−77.5 (2)C22—C25—C26—C2759.3 (2)
C10—C11—C12—C1350.4 (2)C25—C26—C27—O3129.9 (2)
O2—C12—C13—C1558.4 (2)C25—C26—C27—C28−51.7 (2)
C14—C12—C13—C15−60.4 (2)O3—C27—C28—C30−21.1 (3)
C11—C12—C13—C15174.34 (16)C26—C27—C28—C30160.48 (18)
O2—C12—C13—C1−167.31 (16)O3—C27—C28—C2994.0 (2)
C14—C12—C13—C173.9 (2)C26—C27—C28—C29−84.5 (2)
C11—C12—C13—C1−51.4 (2)O3—C27—C28—C21−140.96 (19)
C2—C1—C13—C12171.36 (16)C26—C27—C28—C2140.6 (2)
C9—C1—C13—C12−69.2 (2)C20—C21—C28—C27−167.41 (17)
C6—C1—C13—C1255.8 (2)C22—C21—C28—C27−38.2 (2)
C2—C1—C13—C15−55.8 (2)C20—C21—C28—C3072.3 (2)
C9—C1—C13—C1563.6 (2)C22—C21—C28—C30−158.42 (17)
C6—C1—C13—C15−171.39 (16)C20—C21—C28—C29−47.9 (2)
C12—C13—C15—C16−125.90 (18)C22—C21—C28—C2981.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.84 (1)2.15 (1)2.974 (2)167 (3)

Symmetry codes: (i) −x+2, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5095).

References

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  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mayanti, T., Supratman, U., Mukhtar, M. R., Awang, K. & Ng, S. W. (2009). Acta Cryst. E65, o750. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tjokronegero, R., Mayanti, T., Supratman, U., Mukhtar, M. R. & Ng, S. W. (2009). Acta Cryst. E65, o1448. [PMC free article] [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

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