organic compounds
(1R,4R,5aS,7S,9aS)-7,9a-Dimethyl-6-methylene-3-oxo-1,3,4,5,5a,6,7,8,9,9a-decahydronaphtho[1,2-c]furan-1,4-diyl diacetate
aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
*Correspondence e-mail: ffroncz@lsu.edu
The title compound, C19H24O6, is a sesquiterpene lactone isolated from the Kenyan plant Warburgia ugandensis. Ring A adopts a chair conformation, ring B is in a C2 twist conformation and the lactone ring is nearly planar with maximum deviation 0.007 (1) Å. The reported is based on that of the similar compound bromo-parasiticolide A and is supported by analysis of Bijvoet differences from light atoms in Mo Kα radiation.
Related literature
For related structures, see: Fukuyama et al. (1975) (Bromo-parasiticolide A; PARASB); Ikhiri et al. (1995) (ZOXLIH); Aranda et al. (2001) (ABUKIR); King et al. (1973) (PRPRDE); Rossmann & Lipscomb (1958) (IRSBBZ); Rahbaek et al. (1997) (NEYKOR), Zhang et al. (2006) (UCOLAA, UCOKUT); Harinantenaina et al. (2007) (NIDJUG); McCorkindale et al. (1981) (PEBRLD); Hayashi et al. (2010) (VUTCIX). For the of sesquiterpene see: Fischer et al. (1979). For a description of the Cambridge Structural Database, see: Allen (2002). For the from Bijvoet pairs, see: Hooft et al. (2008). For compounds from Warburgia ugandensis, see: Wube et al. (2005) and for related compounds, see: Garland (1969); Kokwaro (1976).
Experimental
Crystal data
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Data collection: COLLECT (Nonius, 2000); cell DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536812033636/bt5979sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812033636/bt5979Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812033636/bt5979Isup3.cml
Compound I was isolated from the stem bark of Warburgia ugandensis Sprague (Canellaceae) collected in Eldoret, Uasin Gishu District, Kenya. Crystals suitable for diffraction were grown from acetone/hexane/ethyl ether.
H atoms were placed in calculated positions, guided by difference maps, with C—H bond distances 0.95–1.00 Å, Uiso = 1.2Ueq of the attached carbon atom (1.5 for methyl), and thereafter treated as riding. A torsional parameter was refined for each methyl group.
The
and assignment were established in part by analysis of 2776 Bijvoet pairs. Although the refined x = 0.4 (6) (Flack, 1983) is not definitive, the Hooft parameter y = 0.1 (3) and Hooft P2(true) = 0.998 (Hooft et al., 2008) are strong indicators that the reported configuration is correct. This configuration is consistent with that of bromo-parasiticolide A (Fukuyama et al., 1975), CCDC refcode PARASB (Allen, 2002) and with the accepted configuration of sesquiterpene from higher plants (Fischer et al., 1979).Data collection: COLLECT (Nonius, 2000); cell
DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).C19H24O6 | Dx = 1.291 Mg m−3 |
Mr = 348.38 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43212 | Cell parameters from 6310 reflections |
Hall symbol: P 4nw 2abw | θ = 2.5–32.6° |
a = 13.014 (2) Å | µ = 0.10 mm−1 |
c = 21.167 (3) Å | T = 100 K |
V = 3584.9 (9) Å3 | Prism, colorless |
Z = 8 | 0.37 × 0.25 × 0.25 mm |
F(000) = 1488 |
Nonius KappaCCD diffractometer | 6507 independent reflections |
Radiation source: sealed tube | 5934 reflections with I > 2σ(I) |
Horizonally mounted graphite crystal monochromator | Rint = 0.021 |
Detector resolution: 9 pixels mm-1 | θmax = 32.6°, θmin = 3.1° |
ϕ and ω scans | h = −19→19 |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | k = −13→13 |
Tmin = 0.966, Tmax = 0.977 | l = −30→31 |
11378 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.092 | w = 1/[σ2(Fo2) + (0.0489P)2 + 0.548P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
6507 reflections | Δρmax = 0.28 e Å−3 |
231 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Absolute structure: Flack (1983). 2776 Bijvoet pairs |
0 constraints | Absolute structure parameter: 0.4 (6) |
Primary atom site location: structure-invariant direct methods |
C19H24O6 | Z = 8 |
Mr = 348.38 | Mo Kα radiation |
Tetragonal, P43212 | µ = 0.10 mm−1 |
a = 13.014 (2) Å | T = 100 K |
c = 21.167 (3) Å | 0.37 × 0.25 × 0.25 mm |
V = 3584.9 (9) Å3 |
Nonius KappaCCD diffractometer | 6507 independent reflections |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | 5934 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.977 | Rint = 0.021 |
11378 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.092 | Δρmax = 0.28 e Å−3 |
S = 1.02 | Δρmin = −0.21 e Å−3 |
6507 reflections | Absolute structure: Flack (1983). 2776 Bijvoet pairs |
231 parameters | Absolute structure parameter: 0.4 (6) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.99387 (7) | 0.15194 (7) | 0.38460 (4) | 0.01487 (16) | |
C2 | 1.10097 (8) | 0.17487 (8) | 0.41219 (5) | 0.01852 (17) | |
H2A | 1.1216 | 0.2454 | 0.4001 | 0.022* | |
H2B | 1.0972 | 0.172 | 0.4589 | 0.022* | |
C3 | 1.18311 (8) | 0.09896 (9) | 0.38923 (5) | 0.02218 (19) | |
H3A | 1.2483 | 0.1131 | 0.4117 | 0.027* | |
H3B | 1.1952 | 0.11 | 0.3436 | 0.027* | |
C4 | 1.15268 (8) | −0.01396 (8) | 0.40011 (5) | 0.02003 (18) | |
H4 | 1.1451 | −0.0238 | 0.4467 | 0.024* | |
C5 | 1.04822 (8) | −0.03292 (8) | 0.37083 (4) | 0.01737 (17) | |
C6 | 0.96687 (7) | 0.03709 (7) | 0.39832 (4) | 0.01477 (15) | |
H6 | 0.9717 | 0.0288 | 0.4452 | 0.018* | |
C7 | 0.85545 (7) | 0.01232 (8) | 0.38106 (4) | 0.01717 (17) | |
H7A | 0.8433 | −0.0624 | 0.3855 | 0.021* | |
H7B | 0.8425 | 0.0315 | 0.3365 | 0.021* | |
C8 | 0.78177 (8) | 0.07130 (7) | 0.42426 (4) | 0.01629 (17) | |
H8 | 0.711 | 0.0714 | 0.4058 | 0.02* | |
C9 | 0.81884 (7) | 0.17881 (7) | 0.43274 (4) | 0.01617 (16) | |
C10 | 0.75719 (8) | 0.26445 (8) | 0.45837 (5) | 0.01949 (18) | |
C11 | 0.91383 (8) | 0.32891 (8) | 0.42864 (5) | 0.01760 (17) | |
H11 | 0.9261 | 0.3685 | 0.3889 | 0.021* | |
C12 | 0.91114 (7) | 0.21474 (7) | 0.41591 (4) | 0.01502 (16) | |
C13 | 0.99210 (8) | 0.17746 (8) | 0.31324 (4) | 0.02007 (18) | |
H13A | 0.9224 | 0.1675 | 0.2967 | 0.03* | |
H13B | 1.0398 | 0.1319 | 0.2908 | 0.03* | |
H13C | 1.013 | 0.2491 | 0.3069 | 0.03* | |
C14 | 1.23690 (9) | −0.08734 (10) | 0.37789 (6) | 0.0301 (2) | |
H14A | 1.216 | −0.1583 | 0.3865 | 0.045* | |
H14B | 1.3008 | −0.0722 | 0.4005 | 0.045* | |
H14C | 1.2478 | −0.0785 | 0.3324 | 0.045* | |
C15 | 1.02974 (9) | −0.10108 (9) | 0.32528 (5) | 0.0227 (2) | |
H15A | 0.9625 | −0.1076 | 0.3083 | 0.027* | |
H15B | 1.0838 | −0.1431 | 0.3098 | 0.027* | |
C16 | 1.02993 (9) | 0.44956 (8) | 0.47234 (5) | 0.02094 (19) | |
C17 | 1.10061 (10) | 0.46776 (9) | 0.52658 (5) | 0.0266 (2) | |
H17A | 1.139 | 0.5315 | 0.5196 | 0.04* | |
H17B | 1.1487 | 0.4101 | 0.5302 | 0.04* | |
H17C | 1.0605 | 0.4736 | 0.5656 | 0.04* | |
C18 | 0.71756 (8) | −0.05724 (8) | 0.49413 (5) | 0.02047 (18) | |
C19 | 0.72455 (9) | −0.10197 (10) | 0.55937 (5) | 0.0262 (2) | |
H19A | 0.6552 | −0.1138 | 0.5759 | 0.039* | |
H19B | 0.7611 | −0.054 | 0.5871 | 0.039* | |
H19C | 0.7619 | −0.1673 | 0.5577 | 0.039* | |
O1 | 1.00912 (8) | 0.50921 (7) | 0.43108 (4) | 0.0327 (2) | |
O2 | 0.98905 (6) | 0.35231 (6) | 0.47497 (3) | 0.01904 (14) | |
O3 | 0.81477 (6) | 0.35250 (6) | 0.45508 (4) | 0.02120 (15) | |
O4 | 0.67051 (6) | 0.26478 (7) | 0.47800 (4) | 0.02641 (17) | |
O5 | 0.78024 (6) | 0.02495 (6) | 0.48730 (3) | 0.01794 (14) | |
O6 | 0.66441 (8) | −0.09022 (8) | 0.45248 (4) | 0.0323 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0147 (4) | 0.0157 (4) | 0.0142 (4) | −0.0010 (3) | −0.0002 (3) | 0.0010 (3) |
C2 | 0.0154 (4) | 0.0190 (4) | 0.0212 (4) | −0.0020 (3) | −0.0014 (3) | −0.0006 (4) |
C3 | 0.0148 (4) | 0.0253 (5) | 0.0265 (5) | 0.0002 (4) | 0.0006 (4) | −0.0006 (4) |
C4 | 0.0184 (4) | 0.0222 (5) | 0.0195 (4) | 0.0046 (3) | 0.0007 (3) | −0.0013 (3) |
C5 | 0.0191 (4) | 0.0171 (4) | 0.0159 (4) | 0.0011 (3) | 0.0017 (3) | 0.0018 (3) |
C6 | 0.0154 (4) | 0.0153 (4) | 0.0137 (4) | −0.0006 (3) | 0.0001 (3) | 0.0005 (3) |
C7 | 0.0178 (4) | 0.0176 (4) | 0.0161 (4) | −0.0031 (3) | −0.0002 (3) | −0.0014 (3) |
C8 | 0.0149 (4) | 0.0186 (4) | 0.0154 (4) | −0.0019 (3) | −0.0008 (3) | 0.0012 (3) |
C9 | 0.0158 (4) | 0.0168 (4) | 0.0160 (4) | 0.0010 (3) | −0.0007 (3) | −0.0002 (3) |
C10 | 0.0187 (4) | 0.0206 (4) | 0.0192 (4) | 0.0020 (3) | −0.0018 (3) | −0.0011 (3) |
C11 | 0.0185 (4) | 0.0165 (4) | 0.0178 (4) | 0.0004 (3) | −0.0019 (3) | 0.0008 (3) |
C12 | 0.0162 (4) | 0.0152 (4) | 0.0137 (4) | 0.0005 (3) | −0.0020 (3) | 0.0008 (3) |
C13 | 0.0241 (5) | 0.0214 (4) | 0.0147 (4) | −0.0002 (4) | 0.0017 (3) | 0.0038 (3) |
C14 | 0.0222 (5) | 0.0337 (6) | 0.0342 (6) | 0.0087 (4) | 0.0005 (4) | −0.0060 (5) |
C15 | 0.0255 (5) | 0.0218 (5) | 0.0208 (4) | 0.0002 (4) | 0.0027 (4) | −0.0028 (4) |
C16 | 0.0249 (5) | 0.0159 (4) | 0.0220 (4) | −0.0026 (4) | 0.0036 (4) | −0.0028 (3) |
C17 | 0.0311 (6) | 0.0235 (5) | 0.0253 (5) | −0.0089 (4) | −0.0024 (4) | −0.0033 (4) |
C18 | 0.0191 (4) | 0.0222 (4) | 0.0202 (4) | −0.0040 (4) | 0.0008 (4) | 0.0028 (4) |
C19 | 0.0248 (5) | 0.0304 (6) | 0.0233 (5) | −0.0026 (4) | −0.0003 (4) | 0.0089 (4) |
O1 | 0.0492 (6) | 0.0191 (4) | 0.0299 (4) | −0.0068 (4) | −0.0052 (4) | 0.0050 (3) |
O2 | 0.0226 (4) | 0.0154 (3) | 0.0191 (3) | −0.0040 (3) | −0.0034 (3) | 0.0015 (2) |
O3 | 0.0197 (3) | 0.0178 (3) | 0.0261 (3) | 0.0027 (3) | 0.0010 (3) | −0.0020 (3) |
O4 | 0.0181 (3) | 0.0295 (4) | 0.0316 (4) | 0.0029 (3) | 0.0022 (3) | −0.0046 (3) |
O5 | 0.0172 (3) | 0.0207 (3) | 0.0159 (3) | −0.0035 (3) | −0.0009 (2) | 0.0027 (3) |
O6 | 0.0364 (5) | 0.0361 (5) | 0.0243 (4) | −0.0189 (4) | −0.0047 (4) | 0.0026 (3) |
C1—C12 | 1.5054 (14) | C10—O3 | 1.3709 (13) |
C1—C2 | 1.5403 (14) | C11—O2 | 1.4187 (12) |
C1—C13 | 1.5468 (13) | C11—O3 | 1.4386 (13) |
C1—C6 | 1.5627 (13) | C11—C12 | 1.5104 (14) |
C2—C3 | 1.5346 (15) | C11—H11 | 1 |
C2—H2A | 0.99 | C13—H13A | 0.98 |
C2—H2B | 0.99 | C13—H13B | 0.98 |
C3—C4 | 1.5393 (16) | C13—H13C | 0.98 |
C3—H3A | 0.99 | C14—H14A | 0.98 |
C3—H3B | 0.99 | C14—H14B | 0.98 |
C4—C5 | 1.5143 (14) | C14—H14C | 0.98 |
C4—C14 | 1.5279 (15) | C15—H15A | 0.95 |
C4—H4 | 1 | C15—H15B | 0.95 |
C5—C15 | 1.3321 (14) | C16—O1 | 1.1994 (14) |
C5—C6 | 1.5131 (13) | C16—O2 | 1.3740 (12) |
C6—C7 | 1.5297 (14) | C16—C17 | 1.4902 (15) |
C6—H6 | 1 | C17—H17A | 0.98 |
C7—C8 | 1.5313 (14) | C17—H17B | 0.98 |
C7—H7A | 0.99 | C17—H17C | 0.98 |
C7—H7B | 0.99 | C18—O6 | 1.2000 (13) |
C8—O5 | 1.4646 (12) | C18—O5 | 1.3529 (12) |
C8—C9 | 1.4908 (14) | C18—C19 | 1.5013 (15) |
C8—H8 | 1 | C19—H19A | 0.98 |
C9—C12 | 1.3373 (14) | C19—H19B | 0.98 |
C9—C10 | 1.4766 (14) | C19—H19C | 0.98 |
C10—O4 | 1.2021 (13) | ||
C12—C1—C2 | 112.03 (8) | O4—C10—O3 | 121.84 (10) |
C12—C1—C13 | 107.62 (8) | O4—C10—C9 | 129.76 (10) |
C2—C1—C13 | 110.01 (8) | O3—C10—C9 | 108.37 (8) |
C12—C1—C6 | 106.06 (7) | O2—C11—O3 | 107.67 (8) |
C2—C1—C6 | 108.56 (8) | O2—C11—C12 | 110.52 (8) |
C13—C1—C6 | 112.55 (8) | O3—C11—C12 | 104.98 (8) |
C3—C2—C1 | 112.68 (8) | O2—C11—H11 | 111.1 |
C3—C2—H2A | 109.1 | O3—C11—H11 | 111.1 |
C1—C2—H2A | 109.1 | C12—C11—H11 | 111.1 |
C3—C2—H2B | 109.1 | C9—C12—C1 | 124.74 (9) |
C1—C2—H2B | 109.1 | C9—C12—C11 | 108.49 (9) |
H2A—C2—H2B | 107.8 | C1—C12—C11 | 126.58 (9) |
C2—C3—C4 | 112.83 (8) | C1—C13—H13A | 109.5 |
C2—C3—H3A | 109 | C1—C13—H13B | 109.5 |
C4—C3—H3A | 109 | H13A—C13—H13B | 109.5 |
C2—C3—H3B | 109 | C1—C13—H13C | 109.5 |
C4—C3—H3B | 109 | H13A—C13—H13C | 109.5 |
H3A—C3—H3B | 107.8 | H13B—C13—H13C | 109.5 |
C5—C4—C14 | 114.59 (9) | C4—C14—H14A | 109.5 |
C5—C4—C3 | 108.98 (8) | C4—C14—H14B | 109.5 |
C14—C4—C3 | 111.47 (9) | H14A—C14—H14B | 109.5 |
C5—C4—H4 | 107.1 | C4—C14—H14C | 109.5 |
C14—C4—H4 | 107.1 | H14A—C14—H14C | 109.5 |
C3—C4—H4 | 107.1 | H14B—C14—H14C | 109.5 |
C15—C5—C6 | 123.58 (9) | C5—C15—H15A | 120 |
C15—C5—C4 | 124.53 (9) | C5—C15—H15B | 120 |
C6—C5—C4 | 111.88 (8) | H15A—C15—H15B | 120 |
C5—C6—C7 | 116.39 (8) | O1—C16—O2 | 122.57 (10) |
C5—C6—C1 | 110.31 (8) | O1—C16—C17 | 126.69 (10) |
C7—C6—C1 | 111.73 (8) | O2—C16—C17 | 110.74 (9) |
C5—C6—H6 | 105.9 | C16—C17—H17A | 109.5 |
C7—C6—H6 | 105.9 | C16—C17—H17B | 109.5 |
C1—C6—H6 | 105.9 | H17A—C17—H17B | 109.5 |
C6—C7—C8 | 110.20 (8) | C16—C17—H17C | 109.5 |
C6—C7—H7A | 109.6 | H17A—C17—H17C | 109.5 |
C8—C7—H7A | 109.6 | H17B—C17—H17C | 109.5 |
C6—C7—H7B | 109.6 | O6—C18—O5 | 123.49 (10) |
C8—C7—H7B | 109.6 | O6—C18—C19 | 124.89 (10) |
H7A—C7—H7B | 108.1 | O5—C18—C19 | 111.61 (9) |
O5—C8—C9 | 106.34 (7) | C18—C19—H19A | 109.5 |
O5—C8—C7 | 110.25 (8) | C18—C19—H19B | 109.5 |
C9—C8—C7 | 109.86 (8) | H19A—C19—H19B | 109.5 |
O5—C8—H8 | 110.1 | C18—C19—H19C | 109.5 |
C9—C8—H8 | 110.1 | H19A—C19—H19C | 109.5 |
C7—C8—H8 | 110.1 | H19B—C19—H19C | 109.5 |
C12—C9—C10 | 108.79 (9) | C16—O2—C11 | 115.91 (8) |
C12—C9—C8 | 125.92 (9) | C10—O3—C11 | 109.35 (8) |
C10—C9—C8 | 125.23 (9) | C18—O5—C8 | 115.54 (8) |
C12—C1—C2—C3 | 170.06 (8) | C8—C9—C10—O4 | 1.98 (17) |
C13—C1—C2—C3 | −70.28 (11) | C12—C9—C10—O3 | 1.20 (11) |
C6—C1—C2—C3 | 53.28 (10) | C8—C9—C10—O3 | −176.04 (9) |
C1—C2—C3—C4 | −53.11 (12) | C10—C9—C12—C1 | −176.62 (8) |
C2—C3—C4—C5 | 53.61 (11) | C8—C9—C12—C1 | 0.59 (15) |
C2—C3—C4—C14 | −178.93 (9) | C10—C9—C12—C11 | −1.26 (10) |
C14—C4—C5—C15 | −5.67 (16) | C8—C9—C12—C11 | 175.95 (9) |
C3—C4—C5—C15 | 120.00 (11) | C2—C1—C12—C9 | −137.96 (10) |
C14—C4—C5—C6 | 175.82 (9) | C13—C1—C12—C9 | 100.99 (11) |
C3—C4—C5—C6 | −58.51 (10) | C6—C1—C12—C9 | −19.68 (12) |
C15—C5—C6—C7 | 11.94 (14) | C2—C1—C12—C11 | 47.52 (12) |
C4—C5—C6—C7 | −169.54 (8) | C13—C1—C12—C11 | −73.53 (11) |
C15—C5—C6—C1 | −116.70 (11) | C6—C1—C12—C11 | 165.80 (8) |
C4—C5—C6—C1 | 61.83 (10) | O2—C11—C12—C9 | 116.73 (9) |
C12—C1—C6—C5 | −177.79 (7) | O3—C11—C12—C9 | 0.90 (10) |
C2—C1—C6—C5 | −57.24 (9) | O2—C11—C12—C1 | −68.02 (12) |
C13—C1—C6—C5 | 64.78 (10) | O3—C11—C12—C1 | 176.15 (8) |
C12—C1—C6—C7 | 51.08 (9) | O1—C16—O2—C11 | −4.93 (15) |
C2—C1—C6—C7 | 171.64 (8) | C17—C16—O2—C11 | 174.94 (9) |
C13—C1—C6—C7 | −66.34 (10) | O3—C11—O2—C16 | −92.25 (10) |
C5—C6—C7—C8 | 166.12 (8) | C12—C11—O2—C16 | 153.62 (8) |
C1—C6—C7—C8 | −65.93 (10) | O4—C10—O3—C11 | −178.80 (10) |
C6—C7—C8—O5 | −74.35 (10) | C9—C10—O3—C11 | −0.60 (11) |
C6—C7—C8—C9 | 42.52 (10) | O2—C11—O3—C10 | −117.91 (9) |
O5—C8—C9—C12 | 107.52 (10) | C12—C11—O3—C10 | −0.14 (10) |
C7—C8—C9—C12 | −11.78 (13) | O6—C18—O5—C8 | −1.47 (15) |
O5—C8—C9—C10 | −75.71 (11) | C19—C18—O5—C8 | 177.62 (9) |
C7—C8—C9—C10 | 164.99 (9) | C9—C8—O5—C18 | 158.03 (8) |
C12—C9—C10—O4 | 179.22 (11) | C7—C8—O5—C18 | −82.93 (10) |
Experimental details
Crystal data | |
Chemical formula | C19H24O6 |
Mr | 348.38 |
Crystal system, space group | Tetragonal, P43212 |
Temperature (K) | 100 |
a, c (Å) | 13.014 (2), 21.167 (3) |
V (Å3) | 3584.9 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.37 × 0.25 × 0.25 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SCALEPACK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.966, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11378, 6507, 5934 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.757 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.092, 1.02 |
No. of reflections | 6507 |
No. of parameters | 231 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.21 |
Absolute structure | Flack (1983). 2776 Bijvoet pairs |
Absolute structure parameter | 0.4 (6) |
Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Acknowledgements
Purchase of the diffractometer was made possible by grant No. LEQSF(1999–2000)-ESH-TR-13, administered by the Louisiana Board of Regents.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Coloratanolide and drimanolide sesquiterpene lactones, such as title compound I, have been isolated from the stem bark of Warburgia ugandensis Sprague (Canellaceae) as described by Wube et al. (2005). Plants of the genus Warburgia are of interest because of their use by herbalists in Kenya for the treatment of a number of parasitic diseases (Kokwaro, 1976). Compound I is the first sesquiterpene lactone to be crystallographically characterized which has the coloratanolide skeleton, (CAS 60306–54-9). The absolute configuration reported herein is based on the configuration of bromo-parasiticolide A (Fukuyama et al., 1975), CCDC refcode PARASB (Allen, 2002), and supported by analysis of 2776 Bijvoet pairs.