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ISSN: 2056-9890

Corymbolone

aSchool of Agriculture, Food and Wine, The University of Adelaide, Waite Campus, PMB 1, Glen Osmond, SA 5064, Australia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: dennis.taylor@adelaide.edu.au, edward.tiekink@gmail.com

(Received 2 June 2014; accepted 4 June 2014; online 11 June 2014)

The title compound, C15H24O2 [systematic name: (4S,4aR,6R,8aR)-4a-hy­droxy-4,8a-dimethyl-6-(prop-1-en-2-yl)octahydro­naphthalen-1(2H)-one], features two edge-shared six-membered rings with the hydroxyl and methyl substituents at this bridge being trans. One adopts a flattened chair conformation with the C atoms bearing the carbonyl and methyl substituents lying 0.5227 (16) and 0.6621 (15) Å, respectively, above and below the mean plane through the remaining four C atoms (r.m.s. deviation = 0.0145 Å). The second ring, bearing the prop-1-en-2-yl group, has a chair conformation. Supra­molecular helical chains along the b axis are found in the crystal packing, which are sustained by hy­droxy–carbonyl O—H⋯O hydrogen bonding.

Related literature

For the first isolation and the spectroscopic data of corymbolone, see: Garbarino et al. (1985[Garbarino, J. A., Gambaro, V. & Chamy, M. C. (1985). J. Nat. Prod. 48, 323-325.]). For the synthesis of corymbolone in racemic form, see: Ferraz et al. (2006[Ferraz, H. M. C., Souza, A. J. C., Tenius, B. S. M. & Bianco, G. G. (2006). Tetrahedron, 62, 9232-9236.]).

[Scheme 1]

Experimental

Crystal data
  • C15H24O2

  • Mr = 236.34

  • Monoclinic, P 21

  • a = 6.1057 (2) Å

  • b = 12.1389 (2) Å

  • c = 9.2737 (2) Å

  • β = 99.302 (2)°

  • V = 678.30 (3) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 0.58 mm−1

  • T = 100 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]) Tmin = 0.689, Tmax = 1.000

  • 4848 measured reflections

  • 2631 independent reflections

  • 2621 reflections with I > 2σ(I)

  • Rint = 0.011

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.083

  • S = 1.03

  • 2631 reflections

  • 161 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.14 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1200 Friedel pairs

  • Absolute structure parameter: 0.02 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O1i 0.863 (19) 1.993 (19) 2.8513 (12) 172.5 (16)
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+1].

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Technologies Inc., Santa Clara, CA, USA.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Structural commentary top

The title compound, corymbolone, was first characterised in 1985 (Garbarino et al., 1985), and more recently synthesized in racemic form (Ferraz et al., 2006). In the present study, it was isolated from the product mixture that resulted from aerial oxidation of α-guaiene.

The molecular structure of the title molecule, Fig. 1, features two fused six-membered rings. The C2,C3,C5 and C6 atoms of the C1–C6 ring are planar with a r.m.s. deviation of 0.0145 Å, and with the C1 and C4 atoms lying 0.5227 (16) and 0.6621 (15) Å above and below this plane, respectively, so that the conformation of the ring is best described as being a flattened chair. By contrast, the C5–C10 ring closely approximates a chair conformation. With respect to the C1–C6 ring the C1-carbonyl, C4-methyl, C5-hydroxyl and C6-methyl groups have equatorial (eq), axial (ax), ax and eq dispositions, respectively. For the C5–C10 ring, the C5-hydroxyl, C6-methyl and C9-prop-1-en-2-yl groups have have ax, ax and eq dispositions, respectively.

The most prominent feature of the crystal packing is the formation of hydroxyl-O—H···O(carbonyl) hydrogen bonding that leads to helical supra­molecular chains along the b axis (Table 1 and Fig. 2).

Synthesis and crystallization top

Air was slowly bubbled through a neat solution of α-guaiene (7.0 g, 34.3 mmol) and after 21 days the crude mixture of products was subjected to column chromatography with a gradient of 100% hexane to 100% EtOAc. The product (0.12 g, 1.5%) at Rf 0.07 (10% EtOAc/hexane) was collected as a white crystalline solid and recrystallized from hexane to afford block-like colourless crystals of corymboline. M.p. 408–409 K; Lit. M.p. 409–410 K (Garbarino et al., 1985). Spectroscopic data for the title compound are available in the archived CIF.

Refinement top

The hy­droxy-H atom was located in a difference Fourier map and freely refined. C-bound H-atoms were placed in calculated positions [C—H = 0.95 - 1.00 Å] and included in the refinement in the riding model approximation with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms. Owing to poor agreement, two reflections, i.e. (1 1 0) and (2 -4 2), were omitted from the final cycles of refinement.

Related literature top

For the first isolation and the spectroscopic data of corymbolone, see: Garbarino et al. (1985). For the synthesis of corymbolone in racemic form, see: Ferraz et al. (2006).

Structure description top

The title compound, corymbolone, was first characterised in 1985 (Garbarino et al., 1985), and more recently synthesized in racemic form (Ferraz et al., 2006). In the present study, it was isolated from the product mixture that resulted from aerial oxidation of α-guaiene.

The molecular structure of the title molecule, Fig. 1, features two fused six-membered rings. The C2,C3,C5 and C6 atoms of the C1–C6 ring are planar with a r.m.s. deviation of 0.0145 Å, and with the C1 and C4 atoms lying 0.5227 (16) and 0.6621 (15) Å above and below this plane, respectively, so that the conformation of the ring is best described as being a flattened chair. By contrast, the C5–C10 ring closely approximates a chair conformation. With respect to the C1–C6 ring the C1-carbonyl, C4-methyl, C5-hydroxyl and C6-methyl groups have equatorial (eq), axial (ax), ax and eq dispositions, respectively. For the C5–C10 ring, the C5-hydroxyl, C6-methyl and C9-prop-1-en-2-yl groups have have ax, ax and eq dispositions, respectively.

The most prominent feature of the crystal packing is the formation of hydroxyl-O—H···O(carbonyl) hydrogen bonding that leads to helical supra­molecular chains along the b axis (Table 1 and Fig. 2).

For the first isolation and the spectroscopic data of corymbolone, see: Garbarino et al. (1985). For the synthesis of corymbolone in racemic form, see: Ferraz et al. (2006).

Synthesis and crystallization top

Air was slowly bubbled through a neat solution of α-guaiene (7.0 g, 34.3 mmol) and after 21 days the crude mixture of products was subjected to column chromatography with a gradient of 100% hexane to 100% EtOAc. The product (0.12 g, 1.5%) at Rf 0.07 (10% EtOAc/hexane) was collected as a white crystalline solid and recrystallized from hexane to afford block-like colourless crystals of corymboline. M.p. 408–409 K; Lit. M.p. 409–410 K (Garbarino et al., 1985). Spectroscopic data for the title compound are available in the archived CIF.

Refinement details top

The hy­droxy-H atom was located in a difference Fourier map and freely refined. C-bound H-atoms were placed in calculated positions [C—H = 0.95 - 1.00 Å] and included in the refinement in the riding model approximation with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms. Owing to poor agreement, two reflections, i.e. (1 1 0) and (2 -4 2), were omitted from the final cycles of refinement.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the helical supramolecular chain along the b axis in the title compound. The O—H···O hydrogen bonds are shown as orange dashed lines.
(4S,4aR,6R,8aR)-4a-hydroxy-4,8a-dimethyl-6-(prop-1-en-2-yl)octahydronaphthalen-1(2H)-one top
Crystal data top
C15H24O2F(000) = 260
Mr = 236.34Dx = 1.157 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ybCell parameters from 3768 reflections
a = 6.1057 (2) Åθ = 3.6–74.3°
b = 12.1389 (2) ŵ = 0.58 mm1
c = 9.2737 (2) ÅT = 100 K
β = 99.302 (2)°Block, colourless
V = 678.30 (3) Å30.30 × 0.25 × 0.20 mm
Z = 2
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
2631 independent reflections
Radiation source: SuperNova (Cu) X-ray Source2621 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.011
Detector resolution: 10.4041 pixels mm-1θmax = 74.5°, θmin = 6.1°
ω scanh = 77
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
k = 1414
Tmin = 0.689, Tmax = 1.000l = 1111
4848 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0567P)2 + 0.0924P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2631 reflectionsΔρmax = 0.24 e Å3
161 parametersΔρmin = 0.14 e Å3
1 restraintAbsolute structure: Flack (1983), 1200 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (16)
Crystal data top
C15H24O2V = 678.30 (3) Å3
Mr = 236.34Z = 2
Monoclinic, P21Cu Kα radiation
a = 6.1057 (2) ŵ = 0.58 mm1
b = 12.1389 (2) ÅT = 100 K
c = 9.2737 (2) Å0.30 × 0.25 × 0.20 mm
β = 99.302 (2)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector
2631 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2013)
2621 reflections with I > 2σ(I)
Tmin = 0.689, Tmax = 1.000Rint = 0.011
4848 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083Δρmax = 0.24 e Å3
S = 1.03Δρmin = 0.14 e Å3
2631 reflectionsAbsolute structure: Flack (1983), 1200 Friedel pairs
161 parametersAbsolute structure parameter: 0.02 (16)
1 restraint
Special details top

Experimental. Spectroscopic data for the title compound, 1H NMR (600 MHz, CDCl3) δ 4.74 (s, 2H), 2.68 (ddd, J = 17.2, 9.9, 7.8 Hz, 1H), 2.44-2.36 (m, 2H), 2.32 (dddd, J = 12.0, 12.0, 4.2, 4.2 Hz, 1H), 1.93-1.83 (m, 3H), 1.75 (s, 3H), 1.71-1.65 (m, 2H), 1.60 (ddd, J = 13.8, 3.0, 3.0 Hz, 1H), 1.43 (ddd, J = 13.7, 3.7, 2.0 Hz, 1H), 1.37 (dddd, J = 13.3, 13.3, 13.3, 3.6 Hz, 1H), 1.29 (br, 1H), 1.24 (s, 3H), 1.19 (d, J = 7.8 Hz, 3H); 13C NMR (600 MHz, CDCl3) δ 215.8, 149.5, 108.9, 78.6, 51.2, 40.6, 39.4, 37.2, 34.2, 30.2, 28.0, 25.5, 21.1, 20.4, 17.8; MS: m/z (%) 236 (8), 218 (17), 203 (33), 175 (28), 153 (27), 137 (35), 135 (42), 124 (40), 109 (100), 93 (50), 84 (27), 69 (57), 55 (62), 41 (67). All other physical and spectral data were identical to those previously reported by Garbarino et al. (1985).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.00899 (15)0.49702 (8)0.42187 (10)0.0276 (2)
O20.02823 (12)0.20248 (7)0.43171 (9)0.01677 (18)
H20.026 (3)0.1374 (16)0.4692 (19)0.025 (4)*
C10.1255 (2)0.42790 (10)0.47357 (14)0.0195 (2)
C20.2007 (2)0.41919 (11)0.63667 (14)0.0218 (3)
H2A0.09160.45780.68680.026*
H2B0.34440.45790.66200.026*
C30.2279 (2)0.30153 (11)0.69525 (13)0.0204 (3)
H3A0.07930.26870.69460.024*
H3B0.30470.30350.79780.024*
C40.36071 (18)0.22809 (10)0.60493 (12)0.0177 (2)
H40.33630.15060.63520.021*
C50.25743 (17)0.23588 (9)0.44117 (12)0.0145 (2)
C60.24052 (19)0.35347 (10)0.37568 (13)0.0162 (2)
C70.1070 (2)0.34852 (10)0.22026 (13)0.0201 (2)
H7A0.04560.32290.22500.024*
H7B0.09690.42330.17720.024*
C80.2149 (2)0.27089 (11)0.12238 (13)0.0212 (3)
H8A0.36070.30120.10890.025*
H8B0.12040.26680.02510.025*
C90.2478 (2)0.15434 (10)0.18670 (13)0.0179 (2)
H90.09710.12290.18910.021*
C100.37049 (19)0.15834 (9)0.34538 (13)0.0165 (2)
H10A0.37640.08320.38740.020*
H10B0.52490.18330.34570.020*
C110.3657 (2)0.07717 (11)0.09544 (13)0.0234 (3)
C120.5839 (2)0.11391 (13)0.05605 (16)0.0319 (3)
H12A0.65100.05300.00930.048*
H12B0.68370.13630.14480.048*
H12C0.55910.17640.01160.048*
C130.2792 (3)0.02085 (13)0.05543 (16)0.0351 (3)
H13A0.35550.06960.00060.042*
H13B0.14120.04210.08170.042*
C140.6114 (2)0.24905 (12)0.64454 (14)0.0249 (3)
H14A0.68810.21500.57090.037*
H14B0.66640.21700.74060.037*
H14C0.63960.32860.64740.037*
C150.4677 (2)0.40859 (11)0.36941 (14)0.0234 (3)
H15A0.56060.35830.32280.035*
H15B0.54150.42540.46880.035*
H15C0.44450.47690.31270.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0305 (5)0.0183 (5)0.0343 (5)0.0084 (4)0.0058 (4)0.0029 (4)
O20.0142 (4)0.0150 (4)0.0219 (4)0.0027 (3)0.0056 (3)0.0001 (3)
C10.0194 (5)0.0139 (6)0.0266 (6)0.0026 (4)0.0078 (4)0.0024 (5)
C20.0211 (6)0.0228 (6)0.0230 (6)0.0009 (5)0.0076 (4)0.0077 (5)
C30.0181 (5)0.0269 (7)0.0173 (6)0.0012 (5)0.0066 (4)0.0028 (5)
C40.0166 (5)0.0205 (6)0.0169 (5)0.0016 (4)0.0051 (4)0.0001 (4)
C50.0124 (5)0.0145 (5)0.0173 (5)0.0005 (4)0.0047 (4)0.0001 (4)
C60.0172 (5)0.0135 (5)0.0191 (5)0.0007 (4)0.0068 (4)0.0011 (4)
C70.0244 (6)0.0159 (6)0.0203 (5)0.0050 (5)0.0044 (4)0.0032 (5)
C80.0254 (6)0.0223 (6)0.0165 (5)0.0034 (5)0.0050 (4)0.0009 (5)
C90.0173 (5)0.0184 (6)0.0181 (5)0.0024 (4)0.0037 (4)0.0024 (4)
C100.0174 (5)0.0156 (5)0.0172 (5)0.0023 (4)0.0046 (4)0.0008 (4)
C110.0235 (6)0.0291 (7)0.0168 (6)0.0087 (5)0.0011 (5)0.0039 (5)
C120.0321 (7)0.0383 (8)0.0285 (6)0.0116 (6)0.0143 (5)0.0000 (6)
C130.0343 (7)0.0341 (8)0.0352 (7)0.0082 (6)0.0006 (6)0.0173 (6)
C140.0169 (5)0.0379 (8)0.0198 (6)0.0035 (5)0.0024 (4)0.0035 (5)
C150.0251 (6)0.0190 (6)0.0286 (6)0.0078 (5)0.0125 (5)0.0024 (5)
Geometric parameters (Å, º) top
O1—C11.2171 (16)C8—C91.5360 (17)
O2—C51.4459 (12)C8—H8A0.9900
O2—H20.863 (19)C8—H8B0.9900
C1—C21.5117 (17)C9—C111.5193 (16)
C1—C61.5294 (15)C9—C101.5403 (15)
C2—C31.5277 (19)C9—H91.0000
C2—H2A0.9900C10—H10A0.9900
C2—H2B0.9900C10—H10B0.9900
C3—C41.5405 (15)C11—C131.330 (2)
C3—H3A0.9900C11—C121.505 (2)
C3—H3B0.9900C12—H12A0.9800
C4—C141.5365 (16)C12—H12B0.9800
C4—C51.5503 (15)C12—H12C0.9800
C4—H41.0000C13—H13A0.9500
C5—C101.5329 (15)C13—H13B0.9500
C5—C61.5482 (16)C14—H14A0.9800
C6—C71.5380 (16)C14—H14B0.9800
C6—C151.5493 (16)C14—H14C0.9800
C7—C81.5293 (17)C15—H15A0.9800
C7—H7A0.9900C15—H15B0.9800
C7—H7B0.9900C15—H15C0.9800
C5—O2—H2108.0 (11)C7—C8—H8A109.2
O1—C1—C2121.25 (11)C9—C8—H8A109.2
O1—C1—C6121.25 (11)C7—C8—H8B109.2
C2—C1—C6117.28 (10)C9—C8—H8B109.2
C1—C2—C3114.78 (10)H8A—C8—H8B107.9
C1—C2—H2A108.6C11—C9—C8113.31 (10)
C3—C2—H2A108.6C11—C9—C10110.53 (9)
C1—C2—H2B108.6C8—C9—C10110.78 (9)
C3—C2—H2B108.6C11—C9—H9107.3
H2A—C2—H2B107.5C8—C9—H9107.3
C2—C3—C4112.60 (9)C10—C9—H9107.3
C2—C3—H3A109.1C5—C10—C9112.21 (9)
C4—C3—H3A109.1C5—C10—H10A109.2
C2—C3—H3B109.1C9—C10—H10A109.2
C4—C3—H3B109.1C5—C10—H10B109.2
H3A—C3—H3B107.8C9—C10—H10B109.2
C14—C4—C3111.45 (10)H10A—C10—H10B107.9
C14—C4—C5117.12 (9)C13—C11—C12121.63 (13)
C3—C4—C5109.32 (9)C13—C11—C9120.31 (13)
C14—C4—H4106.1C12—C11—C9118.04 (12)
C3—C4—H4106.1C11—C12—H12A109.5
C5—C4—H4106.1C11—C12—H12B109.5
O2—C5—C10108.35 (9)H12A—C12—H12B109.5
O2—C5—C6103.43 (8)C11—C12—H12C109.5
C10—C5—C6110.27 (9)H12A—C12—H12C109.5
O2—C5—C4106.19 (8)H12B—C12—H12C109.5
C10—C5—C4112.35 (9)C11—C13—H13A120.0
C6—C5—C4115.55 (9)C11—C13—H13B120.0
C1—C6—C7110.78 (10)H13A—C13—H13B120.0
C1—C6—C5108.65 (9)C4—C14—H14A109.5
C7—C6—C5108.86 (10)C4—C14—H14B109.5
C1—C6—C15105.47 (10)H14A—C14—H14B109.5
C7—C6—C15108.88 (9)C4—C14—H14C109.5
C5—C6—C15114.18 (9)H14A—C14—H14C109.5
C8—C7—C6111.50 (9)H14B—C14—H14C109.5
C8—C7—H7A109.3C6—C15—H15A109.5
C6—C7—H7A109.3C6—C15—H15B109.5
C8—C7—H7B109.3H15A—C15—H15B109.5
C6—C7—H7B109.3C6—C15—H15C109.5
H7A—C7—H7B108.0H15A—C15—H15C109.5
C7—C8—C9112.27 (9)H15B—C15—H15C109.5
O1—C1—C2—C3140.04 (12)C10—C5—C6—C758.86 (11)
C6—C1—C2—C345.32 (15)C4—C5—C6—C7172.39 (9)
C1—C2—C3—C447.77 (14)O2—C5—C6—C15178.70 (9)
C2—C3—C4—C1479.04 (13)C10—C5—C6—C1563.02 (12)
C2—C3—C4—C552.02 (12)C4—C5—C6—C1565.72 (12)
C14—C4—C5—O2174.50 (10)C1—C6—C7—C8177.79 (10)
C3—C4—C5—O257.55 (11)C5—C6—C7—C858.38 (12)
C14—C4—C5—C1056.22 (14)C15—C6—C7—C866.66 (13)
C3—C4—C5—C10175.83 (9)C6—C7—C8—C955.87 (13)
C14—C4—C5—C671.50 (13)C7—C8—C9—C11176.99 (10)
C3—C4—C5—C656.45 (11)C7—C8—C9—C1052.10 (13)
O1—C1—C6—C720.66 (16)O2—C5—C10—C955.14 (12)
C2—C1—C6—C7164.70 (10)C6—C5—C10—C957.40 (12)
O1—C1—C6—C5140.19 (11)C4—C5—C10—C9172.14 (9)
C2—C1—C6—C545.17 (13)C11—C9—C10—C5179.72 (10)
O1—C1—C6—C1596.99 (13)C8—C9—C10—C553.27 (13)
C2—C1—C6—C1577.64 (13)C8—C9—C11—C13128.63 (13)
O2—C5—C6—C163.91 (10)C10—C9—C11—C13106.35 (14)
C10—C5—C6—C1179.59 (9)C8—C9—C11—C1253.00 (15)
C4—C5—C6—C151.67 (11)C10—C9—C11—C1272.02 (14)
O2—C5—C6—C756.81 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.863 (19)1.993 (19)2.8513 (12)172.5 (16)
Symmetry code: (i) x, y1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.863 (19)1.993 (19)2.8513 (12)172.5 (16)
Symmetry code: (i) x, y1/2, z+1.
 

Acknowledgements

This project was supported in part by the School of Agriculture, Food and Wine, The University of Adelaide, and by Australia's grape growers and wine makers through their investment body, the Grape and Wine Research and Development Corporation, with matching funds from the Australian Government. SB thanks the Faculty of Science for a PhD scholarship. Intensity data were provided by the University of Malaya Crystallographic Laboratory. We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

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