Download citation
Download citation
link to html
The title compound, 2,10-di­hydroxy-1,6,10-tri­methyl-4,14-dioxatri­cyclo­[9.2.1.03,7]­tetradecan-5-one, C15H24O5, a novel sesquiterpene lactone synthesized from di­hydro­parthenolide, has a 1,4-furano bridge in the 10-membered ring and a trans-fused α-methyl-γ-lactone.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801004111/cv6008sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801004111/cv6008Isup2.hkl
Contains datablock I

CCDC reference: 162816

Key indicators

  • Single-crystal X-ray study
  • T = 300 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.128
  • Data-to-parameter ratio = 15.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
RADNW_01 Alert C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 1.54175-1.54180 Wavelength given = 1.54184 STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack -0.300 From the CIF: _refine_ls_abs_structure_Flack_su 0.200 Alert C Flack parameter is too small General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 76.00 From the CIF: _reflns_number_total 2975 Count of symmetry unique reflns 1758 Completeness (_total/calc) 169.23% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1217 Fraction of Friedel pairs measured 0.692 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

The α,β-unsaturated lactones have aroused much interest in medicine because of their remarkable biological properties, mainly as cytotoxic, antitumor, and bactericidal agents (El-Feraly & Chan, 1978). Among these compounds, sesquiterpenes (α-methylene-γ-lactones) have been intensively studied using both medicinal and chemical approaches (Picman, 1986). Recently, it has been shown that sesquiterpene lactones stimulate germination of Striga seeds at concentrations lower than 10-5 M (Rugutt, 1996). Striga (witchweed) are parasitic weeds that cause severe damage to graminaceous and leguminous crops in tropical and semitropical areas of the eastern hemisphere (Nour et al., 1983).

We have recently begun a program aimed at synthesis and separation (Shamsi & Warner, 1997) of antimycobacterial agents. Specifically, a long-range goal of our efforts in this area is to rationally design novel classes of drugs against the multidrug-resistant Mycobacterium tuberculosis and M. avium. It is important to recognize that dihydroparthenolide contains the 4,5-epoxide as a reactive receptor site. Although this epoxide function is not directly accessible due to steric hindrance of the associated medium ring structure, it provides increased reactivity as well as regio- and stereospecificity of subsequent intramolecular cyclizations. We envision that the reaction of dihydroparthenolide with OsO4 lead to the formation of a 1,10-diol (both OH α-oriented). This diol undergoes a Markovnikov-type transannular cyclization to afford dihydroparthenolide diol, (I). In the 400 MHz 1H NMR spectrum of (I), a doublet at δ 3.66 was attributed to H-5 which coupled with H-6. The signal of H-6 (δ 4.17) appeared as a well defined one-proton of doublet with large coupling constants (J5,6 = 10.4 Hz; J6,7 = 7.2 Hz). This indicated a trans-axial relationship between H-5, H-6 and H-7, i.e. H-5 α, H-6 β, and H-7 α-oriented. The stereochemistry of methylene proton resonances (which overlapped at δ 1.4–2.3) could not be determined from the NMR data. In order to unambiguously assign the stereochemistry of dihydroparthenolide diol, the crystal structure was determined.

The structure (Fig. 1) is identical to that of the naturally occurring achillifolin (Ulubelen, et al., 1990), except that the title compound has a β-methyl group and an α-OH at C10 rather than an exocyclic CH2 group. The tetrahydrofuran ring has the half-chair conformation with O3 on the twist axis, and asymmetry parameter (Duax & Norton, 1975) ΔC2 = 3.5°. The α-methyl-γ-lactone is trans-fused at C6—C7, and has its methyl group α-oriented, with C11 having the S configuration. The conformation of the lactone ring is an envelope, with C7 at the flap position, and asymmetry parameter ΔCs = 1.0°. O—H···O hydrogen bonding (Table 2) form chains in the [010] direction. The crystal structure of dihydroparthenolide has been reported (Rugutt & Rugutt, 1997).

Dihydroparthenolide diol and dihydroparthenolide were tested against Mycobacterium tuberculosis and M. avium. Stock solutions (10.24 mg ml-1) were dissolved in DMSO and filter sterilized. The bioassay was performed by a broth dilution method as previously reported (Franzblau, 1989). The MICs of both compounds against M. tuberculosis and M. avium was 128 µg ml-1. The minimum inhibitory concentration (MIC) is the lowest concentration of the compound needed to inhibit 99% of the organisms.

Experimental top

The leaves of Ambrosia artemisifolia (1.0 kg) was exhaustively extracted by percolation with methanol following the method described by El-Feraly (1978). The methanol was evaporated in vacuo to afford 72 g of gummy residue, which was chromatographed on 800 g of silica gel and eluted with hexane and increasing amounts of ethyl acetate (EtOAc). Hexane–EtOAc (15:85) afforded fractions, which after repeated crystallizations from methanol yielded dihydroparthenolide as colorless needles. Dihydroparthenolide diol was synthesized by subjecting dihydroparthenolide to dihydroxylation (Norby et al., 1999) with OsO4 under catalytic conditions. To a cold solution of 4-methylmorpholine N-oxide (0.8 g, 4.4 mmol) in water (2.5 ml) and acetone (1.0 ml) was added a solution of OsO4 (1% in t-BuOH, 0.33 ml, 1.3 × 10 -5 mol). Dihydroparthenolide (1.1 g, 4.4 mmol) was added, and the reaction mixture stirred for 20 h. The reaction mixture was chromatographed on silica gel (hexane–EtOAc (1:4)) to afford colorless crystals of dihydroparthenolide diol in 85% yield.

Refinement top

The absolute configuration was determined by refinement of the Flack parameter. The reported configuration, which agrees with that of sesquiterpene lactones from higher plants (Fischer et al., 1979), yielded x = -0.3 (2), while the inverse configuration yielded x = 1.3 (2). The OH H-atom positions were located in a difference Fourier map and refined isotropically, with Uiso = 1.5Ueq(O). Other H atoms were placed in calculated positions with C—H bond distances 0.97 (CH), 0.97 (CH2) and 0.96 Å (CH3), Uiso = 1.2Ueq of the attached C atom (1.5 for methyl), and thereafter treated as riding. A torsional parameter was refined for each methyl group.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: maXus (Mackay et al., 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The atom-numbering scheme for (I) with ellipsoids at the 30% probability level.
2,10-dihydroxy-1,6,10-trimethyl-4,14-dioxztricyclo[9.2.1.0<3,7>] tetradecan-5-one top
Crystal data top
C15H24O5Dx = 1.291 Mg m3
Mr = 284.34Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 9.2706 (13) Åθ = 21.3–42.2°
b = 10.4565 (8) ŵ = 0.79 mm1
c = 15.094 (3) ÅT = 300 K
V = 1463.2 (4) Å3Fragment, colorless
Z = 40.38 × 0.32 × 0.17 mm
F(000) = 616
Data collection top
Enraf-Nonius CAD-4
diffractometer
2731 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 76.0°, θmin = 5.1°
ω–2θ scansh = 011
Absorption correction: ψ scan
(North, et al, 1968)
k = 013
Tmin = 0.808, Tmax = 0.875l = 1818
3269 measured reflections3 standard reflections every 40 min
2975 independent reflections intensity decay: 3.3%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.078P)2 + 0.2091P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.128(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.17 e Å3
2975 reflectionsΔρmin = 0.15 e Å3
191 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0042 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: (Flack, 1983), 1217 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.3 (2)
Crystal data top
C15H24O5V = 1463.2 (4) Å3
Mr = 284.34Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 9.2706 (13) ŵ = 0.79 mm1
b = 10.4565 (8) ÅT = 300 K
c = 15.094 (3) Å0.38 × 0.32 × 0.17 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
2731 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North, et al, 1968)
Rint = 0.018
Tmin = 0.808, Tmax = 0.8753 standard reflections every 40 min
3269 measured reflections intensity decay: 3.3%
2975 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128Δρmax = 0.17 e Å3
S = 1.07Δρmin = 0.15 e Å3
2975 reflectionsAbsolute structure: (Flack, 1983), 1217 Friedel pairs
191 parametersAbsolute structure parameter: 0.3 (2)
0 restraints
Special details top

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
O10.25990 (19)0.39108 (13)0.31506 (12)0.0585 (4)
O20.3331 (2)0.20483 (16)0.36804 (16)0.0809 (6)
O30.19097 (14)0.77712 (13)0.35784 (9)0.0413 (3)
O40.2259 (2)0.54554 (17)0.18149 (11)0.0614 (5)
H4O0.303 (4)0.502 (4)0.162 (2)0.092*
O50.50052 (18)0.98461 (15)0.40080 (14)0.0639 (5)
H5O0.455 (4)1.063 (4)0.403 (2)0.096*
C10.2748 (2)0.89276 (18)0.35280 (14)0.0448 (4)
H10.21100.96520.36530.054*
C20.3248 (3)0.9029 (2)0.25695 (16)0.0610 (6)
H2A0.33130.99140.23820.073*
H2B0.41780.86200.24870.073*
C30.2076 (3)0.8328 (2)0.20715 (15)0.0581 (6)
H3A0.24360.79910.15150.070*
H3B0.12620.88860.19530.070*
C40.1657 (2)0.7254 (2)0.27012 (12)0.0436 (4)
C50.2678 (2)0.61033 (19)0.25950 (13)0.0432 (4)
H50.36650.64210.25190.052*
C60.2624 (2)0.52513 (17)0.34328 (14)0.0423 (4)
H60.17380.54400.37620.051*
C70.3911 (2)0.52959 (18)0.40717 (13)0.0385 (4)
H70.47970.52600.37190.046*
C80.4010 (2)0.64537 (18)0.46861 (13)0.0440 (4)
H8A0.45320.62070.52160.053*
H8B0.30420.66970.48640.053*
C90.4760 (2)0.76292 (19)0.42726 (17)0.0483 (5)
H9A0.56470.77770.45980.058*
H9B0.50300.74080.36710.058*
C100.3930 (2)0.88970 (19)0.42385 (15)0.0458 (5)
C110.3721 (2)0.39996 (18)0.45337 (14)0.0443 (4)
H110.29320.40750.49620.053*
C120.3218 (3)0.3185 (2)0.37812 (17)0.0544 (5)
C130.5020 (3)0.3444 (2)0.50059 (17)0.0568 (6)
H13A0.47640.26380.52680.085*
H13B0.53310.40230.54610.085*
H13C0.57880.33180.45880.085*
C140.3308 (3)0.9239 (2)0.51443 (16)0.0559 (5)
H14A0.40500.91720.55850.084*
H14B0.25370.86600.52860.084*
H14C0.29441.00980.51310.084*
C150.0085 (3)0.6876 (3)0.26291 (16)0.0577 (6)
H15A0.01020.61620.30120.087*
H15B0.01290.66430.20280.087*
H15C0.05110.75850.28020.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0715 (10)0.0304 (7)0.0735 (10)0.0018 (7)0.0253 (8)0.0044 (7)
O20.0971 (14)0.0308 (8)0.1149 (17)0.0011 (8)0.0369 (13)0.0002 (9)
O30.0477 (7)0.0342 (6)0.0419 (7)0.0009 (5)0.0015 (5)0.0019 (5)
O40.0746 (11)0.0612 (10)0.0484 (9)0.0130 (8)0.0114 (8)0.0124 (8)
O50.0526 (9)0.0334 (7)0.1056 (14)0.0063 (7)0.0076 (9)0.0059 (8)
C10.0526 (10)0.0291 (8)0.0528 (11)0.0048 (8)0.0053 (9)0.0040 (8)
C20.0815 (16)0.0440 (11)0.0575 (13)0.0012 (11)0.0160 (12)0.0131 (10)
C30.0792 (16)0.0485 (12)0.0466 (11)0.0099 (11)0.0054 (11)0.0134 (9)
C40.0507 (10)0.0430 (10)0.0372 (9)0.0076 (9)0.0007 (8)0.0035 (8)
C50.0489 (10)0.0395 (9)0.0413 (9)0.0042 (8)0.0027 (8)0.0017 (8)
C60.0462 (10)0.0287 (8)0.0519 (10)0.0002 (7)0.0058 (8)0.0013 (8)
C70.0426 (9)0.0296 (8)0.0433 (9)0.0011 (7)0.0013 (7)0.0036 (7)
C80.0502 (10)0.0351 (9)0.0468 (10)0.0001 (8)0.0055 (8)0.0002 (8)
C90.0406 (9)0.0334 (9)0.0710 (13)0.0011 (8)0.0032 (9)0.0012 (9)
C100.0434 (10)0.0289 (9)0.0650 (12)0.0009 (7)0.0018 (9)0.0013 (9)
C110.0480 (10)0.0323 (9)0.0527 (11)0.0002 (8)0.0001 (8)0.0083 (8)
C120.0567 (12)0.0332 (10)0.0732 (14)0.0024 (8)0.0126 (11)0.0050 (9)
C130.0640 (13)0.0438 (11)0.0625 (13)0.0024 (11)0.0102 (11)0.0133 (10)
C140.0604 (13)0.0442 (11)0.0630 (13)0.0041 (10)0.0052 (10)0.0096 (10)
C150.0507 (11)0.0700 (15)0.0525 (12)0.0081 (11)0.0086 (10)0.0035 (11)
Geometric parameters (Å, º) top
O1—C121.346 (3)C6—H60.9800
O1—C61.465 (2)C7—C81.528 (3)
O2—C121.203 (3)C7—C111.534 (2)
O3—C11.439 (2)C7—H70.9800
O3—C41.450 (2)C8—C91.544 (3)
O4—C51.413 (2)C8—H8A0.9700
O4—H4O0.90 (4)C8—H8B0.9700
O5—C101.449 (2)C9—C101.534 (3)
O5—H5O0.92 (4)C9—H9A0.9700
C1—C21.523 (3)C9—H9B0.9700
C1—C101.534 (3)C10—C141.526 (3)
C1—H10.9800C11—C121.495 (3)
C2—C31.511 (4)C11—C131.515 (3)
C2—H2A0.9700C11—H110.9800
C2—H2B0.9700C13—H13A0.9600
C3—C41.522 (3)C13—H13B0.9600
C3—H3A0.9700C13—H13C0.9600
C3—H3B0.9700C14—H14A0.9600
C4—C151.514 (3)C14—H14B0.9600
C4—C51.539 (3)C14—H14C0.9600
C5—C61.548 (3)C15—H15A0.9600
C5—H50.9800C15—H15B0.9600
C6—C71.535 (3)C15—H15C0.9600
C12—O1—C6109.11 (16)C7—C8—C9114.36 (18)
C1—O3—C4110.65 (14)C7—C8—H8A108.7
C5—O4—H4O107 (2)C9—C8—H8A108.7
C10—O5—H5O107 (2)C7—C8—H8B108.7
O3—C1—C2105.84 (17)C9—C8—H8B108.7
O3—C1—C10109.36 (15)H8A—C8—H8B107.6
C2—C1—C10116.6 (2)C10—C9—C8118.40 (17)
O3—C1—H1108.2C10—C9—H9A107.7
C2—C1—H1108.2C8—C9—H9A107.7
C10—C1—H1108.2C10—C9—H9B107.7
C3—C2—C1102.71 (19)C8—C9—H9B107.7
C3—C2—H2A111.2H9A—C9—H9B107.1
C1—C2—H2A111.2O5—C10—C14108.36 (18)
C3—C2—H2B111.2O5—C10—C1108.02 (18)
C1—C2—H2B111.2C14—C10—C1110.57 (18)
H2A—C2—H2B109.1O5—C10—C9104.78 (16)
C2—C3—C4103.34 (18)C14—C10—C9111.21 (19)
C2—C3—H3A111.1C1—C10—C9113.57 (17)
C4—C3—H3A111.1C12—C11—C13112.78 (18)
C2—C3—H3B111.1C12—C11—C7101.18 (16)
C4—C3—H3B111.1C13—C11—C7117.50 (17)
H3A—C3—H3B109.1C12—C11—H11108.3
O3—C4—C15108.58 (17)C13—C11—H11108.3
O3—C4—C3104.68 (17)C7—C11—H11108.3
C15—C4—C3113.16 (19)O2—C12—O1120.3 (2)
O3—C4—C5106.71 (15)O2—C12—C11129.2 (2)
C15—C4—C5112.40 (19)O1—C12—C11110.44 (17)
C3—C4—C5110.79 (17)C11—C13—H13A109.5
O4—C5—C4107.00 (17)C11—C13—H13B109.5
O4—C5—C6113.33 (16)H13A—C13—H13B109.5
C4—C5—C6110.16 (16)C11—C13—H13C109.5
O4—C5—H5108.8H13A—C13—H13C109.5
C4—C5—H5108.8H13B—C13—H13C109.5
C6—C5—H5108.8C10—C14—H14A109.5
O1—C6—C7102.93 (15)C10—C14—H14B109.5
O1—C6—C5108.27 (16)H14A—C14—H14B109.5
C7—C6—C5118.07 (16)C10—C14—H14C109.5
O1—C6—H6109.1H14A—C14—H14C109.5
C7—C6—H6109.1H14B—C14—H14C109.5
C5—C6—H6109.1C4—C15—H15A109.5
C8—C7—C11115.53 (16)C4—C15—H15B109.5
C8—C7—C6116.88 (16)H15A—C15—H15B109.5
C11—C7—C699.78 (15)C4—C15—H15C109.5
C8—C7—H7108.0H15A—C15—H15C109.5
C11—C7—H7108.0H15B—C15—H15C109.5
C6—C7—H7108.0
C4—O3—C1—C29.1 (2)O1—C6—C7—C1138.4 (2)
C4—O3—C1—C10135.49 (16)C5—C6—C7—C11157.55 (16)
O3—C1—C2—C327.9 (2)C11—C7—C8—C9157.72 (17)
C10—C1—C2—C3149.75 (18)C6—C7—C8—C985.3 (2)
C1—C2—C3—C435.5 (2)C7—C8—C9—C10123.2 (2)
C1—O3—C4—C15134.60 (18)O3—C1—C10—O5162.79 (15)
C1—O3—C4—C313.5 (2)C2—C1—C10—O542.8 (2)
C1—O3—C4—C5104.03 (17)O3—C1—C10—C1478.8 (2)
C2—C3—C4—O330.6 (2)C2—C1—C10—C14161.21 (19)
C2—C3—C4—C15148.6 (2)O3—C1—C10—C947.0 (2)
C2—C3—C4—C584.1 (2)C2—C1—C10—C973.0 (2)
O3—C4—C5—O4169.53 (16)C8—C9—C10—O5167.66 (19)
C15—C4—C5—O450.6 (2)C8—C9—C10—C1450.8 (3)
C3—C4—C5—O477.1 (2)C8—C9—C10—C174.7 (3)
O3—C4—C5—C645.9 (2)C8—C7—C11—C12163.36 (17)
C15—C4—C5—C673.0 (2)C6—C7—C11—C1237.16 (19)
C3—C4—C5—C6159.33 (18)C8—C7—C11—C1373.4 (2)
C12—O1—C6—C725.4 (2)C6—C7—C11—C13160.37 (19)
C12—O1—C6—C5151.16 (19)C6—O1—C12—O2179.0 (3)
O4—C5—C6—O118.0 (2)C6—O1—C12—C110.7 (3)
C4—C5—C6—O1137.79 (18)C13—C11—C12—O227.5 (4)
O4—C5—C6—C7134.27 (19)C7—C11—C12—O2153.9 (3)
C4—C5—C6—C7105.9 (2)C13—C11—C12—O1150.6 (2)
O1—C6—C7—C8163.68 (17)C7—C11—C12—O124.2 (2)
C5—C6—C7—C877.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O5i0.90 (4)2.06 (4)2.895 (3)154 (3)
O5—H5O···O2ii0.92 (4)1.94 (4)2.821 (2)160 (3)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC15H24O5
Mr284.34
Crystal system, space groupOrthorhombic, P212121
Temperature (K)300
a, b, c (Å)9.2706 (13), 10.4565 (8), 15.094 (3)
V3)1463.2 (4)
Z4
Radiation typeCu Kα
µ (mm1)0.79
Crystal size (mm)0.38 × 0.32 × 0.17
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North, et al, 1968)
Tmin, Tmax0.808, 0.875
No. of measured, independent and
observed [I > 2σ(I)] reflections
3269, 2975, 2731
Rint0.018
(sin θ/λ)max1)0.629
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.128, 1.07
No. of reflections2975
No. of parameters191
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.15
Absolute structure(Flack, 1983), 1217 Friedel pairs
Absolute structure parameter0.3 (2)

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, maXus (Mackay et al., 1999), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97.

Selected torsion angles (º) top
C4—O3—C1—C29.1 (2)C5—C6—C7—C877.2 (2)
O3—C1—C2—C327.9 (2)O1—C6—C7—C1138.4 (2)
C10—C1—C2—C3149.75 (18)C6—C7—C8—C985.3 (2)
C1—C2—C3—C435.5 (2)C7—C8—C9—C10123.2 (2)
C1—O3—C4—C313.5 (2)C2—C1—C10—C973.0 (2)
C2—C3—C4—O330.6 (2)C8—C9—C10—C174.7 (3)
C2—C3—C4—C584.1 (2)C6—C7—C11—C1237.16 (19)
C3—C4—C5—C6159.33 (18)C6—O1—C12—C110.7 (3)
C12—O1—C6—C725.4 (2)C7—C11—C12—O124.2 (2)
C4—C5—C6—C7105.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O5i0.90 (4)2.06 (4)2.895 (3)154 (3)
O5—H5O···O2ii0.92 (4)1.94 (4)2.821 (2)160 (3)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds