Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 8| August 2009| Pages o1867-o1868
doi:10.1107/S1600536809026701

Cynaratriol, a sesquiterpene lactone from Centaurea musimomum

Matías López-Rodríguez,a Victor P. García,b Hanêne Zater,c Samir Benayached and Fadila Benayachec*

aInstituto de Bioorgánica "A. González", Universidad de La Laguna, Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain, bInstituto de Productos Naturales y Agrobiología del CSIC, Instituto de Bioorgánica "A. González", Universidad de La Laguna, Astrofísico Francisco Sánchez, 2, 38206 La Laguna, Tenerife, Spain, cLaboratoire de Phytochemie et Analyses Physico-Chimiques et Biologiques, Equipe Associée à l'ANDRS, Université Mentouri, Route de Aïn El Bey, 25000 Constantine, Algeria, and dLaboratoire de Valorisation des Resources Naturelles et Synthèse de Substances, Bioactives, Equipe Associée à l'ANDRS, Université Mentouri, Route de Aïn El Bey, 25000 Constantine, Algeria
*Correspondence e-mail: malopez@ull.es

(Received 30 June 2009; accepted 8 July 2009; online 15 July 2009)

The title compound [systematic name: 3,8-dihydr­oxy-3-(hydroxy­meth­yl)-9-methyl-6-methyl­enedeca­hydro­azuleno[4,5-b]furan-2(3H)-one], C15H22O5, is a sesquiterpene lactone showing the typical tricyclic guaianolide skeleton which has been isolated, together with other related metabolites, from the plant Centaurea musimomum. The present study confirms the mol­ecular structure, assigned by 1H NMR and MS spectroscopy, as well as the the 11β-hydroxy­methyl, 3β-hydr­oxy and 4α-methyl stereochemistry. The crystal structure is built through a network of O—H⋯O hydrogen bonds involving the three hydroxyl groups that are present in the mol­ecular skeleton.

Related literature

For the ethyl acetate soluble extract of Centaurea musimomum, an endemic specie from Algeria, see: Quezel & Santa (1963[Quezel, P. & Santa, S. (1963). Nouvelle flore de l'Algérie et des régions désertiques méridionales. Paris, Editions du CNRS.]). For the structures of several guaianolide type sesquiterpene lactones isolated from the chloro­form-soluble part of Centaurea musimomum, see: Medjroubi et al. (1997[Medjroubi, K., Benayache, F., Benayache, S., Akkal, S., Khalfallah, N. & Aclinou, P. (1997). Phytochemistry, 45, 1449-1452.], 2003[Medjroubi, K., Benayache, F., León, F. & Bermejo, J. (2003). Rev. Colombiana Quim., 32, 17-25.], 2005[Medjroubi, K., Benayache, F. & Bermejo, J. (2005). Fitoterapia, 76, 744-745.]); González-Platas et al. (1999[González-Platas, J., Ruiz-Pérez, C., González, A. G., Bermejo, J. & Medjroubi, K. (1999). Acta Cryst. C55, 1837-1839.]). Cynaratriol was previously isolated from Cynara species, see: von Heinz et al. (1979[Heinz, B. O. von, Thiele, K. & Pretsch, E. (1979). Helv. Chim. Acta, 62, 1289-1297.]). For related structures, see: Oksuz et al. (1993[Oksuz, S., Clark, R. J. & Herz, W. (1993). Phytochem, 33, 1267.]); González-Platas et al. (1999[González-Platas, J., Ruiz-Pérez, C., González, A. G., Bermejo, J. & Medjroubi, K. (1999). Acta Cryst. C55, 1837-1839.]).

[Scheme 1]

Experimental

Crystal data

  • C15H22O5

  • Mr = 282.33

  • Orthorhombic, P 21 21 21

  • a = 8.417 (4) Å

  • b = 9.919 (3) Å

  • c = 17.187 (8) Å

  • V = 1434.9 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.40 × 0.30 × 0.25 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: none

  • 8829 measured reflections

  • 2054 independent reflections

  • 1847 reflections with I > 2σ(I)

  • Rint = 0.038
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.101

  • S = 1.11

  • 2054 reflections

  • 194 parameters

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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O4—H4O⋯O1i 0.84 (3) 1.93 (3) 2.756 (2) 169 (3)
O5—H5O⋯O3ii 0.86 (3) 1.99 (3) 2.844 (2) 176 (3)
O1—H1O⋯O3iii 0.76 (4) 2.26 (4) 2.978 (3) 159 (4)
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (iii) [-x-{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026701/bx2222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026701/bx2222Isup2.hkl

checkCIF report


Comment top

The Centaurea genus plants are a natural source of various type of sesquiterpenic lactones, many of which have been shown to be biologically active: Medjroubi, Benayache & Bermejo. In connection with a systematic study of this genus, we have investigated the ethyl acetate soluble extract of Centaurea musimomum, an endemic specie from Algeria: Quezel & Santa, (1963). Our previous phytochemical study of the chloroform soluble part led to the isolation an molecular structure determination of several guaianolide type sesquiterpene lactones: Medjroubi et al., 1997; González-Platas et al. 1999; Medjroubi et al., 2003. Cynaratriol was previously isolated from Cynara species (Heinz, Thiele & Pretsch, 1979). In this work we report the isolation and the molecular and crystal structure determination of the title compound, which it is described for the first time as a metabolite for the Centaurea genus. The lack of suitable anomalous scatters did not allow us to reliably determine the absolute structure and that shown was chosen to be the same as that the, close related, 4β,15-Dihydro-3-dehydrosolstiatilin A (González-Platas et al., 1999) and its acetate (Oksuz, Clark & Herz, 1993).

Related literature top

For the ethyl acetate soluble extract of Centaurea musimomum, an endemic specie from Algeria, see: Quezel & Santa (1963). For the structures of several guaianolide type sesquiterpene lactones isolated from the chloroform-soluble part of Centaurea musimomum, see: Medjroubi et al. (1997, 2003, 2005); González-Platas et al. (1999). Cynaratriol was previously isolated from Cynara species, see: von Heinz et al. (1979). For related structures, see: Oksuz et al. (1993); González-Platas et al. (1999).

For related literature, see: González-Platas, Ruiz-Pérez, González, Bermejo & Medjroubi (1999).

Refinement top

The H-atoms of the hydroxyl groups were located on difference-Fourier map and freely refined. All other H atoms were positioned with idealized geometry: C—H = 0.98(CH3), 0.99(CH2), 1.00(CH) Å and included in the refinement in a riding-model approximation with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq for methyl. The lack of suitable anomalous scatters did not allow us to reliably determine the absolute structure according to the Flack parameters: -10 (10) and, therefore, the Friedel pairs were merged prior to the final refinement.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of cynaratriol represented showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. A view of the hydrogen-bonding network. Hydrogen atoms not involved in the O—H···O interactions have been omitted.
3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylenedecahydroazuleno[4,5-b]furan-2(3H)-one top
Crystal data top
C15H22O5F(000) = 608
Mr = 282.33Dx = 1.307 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7053 reflections
a = 8.417 (4) Åθ = 3.2–28.6°
b = 9.919 (3) ŵ = 0.10 mm−1
c = 17.187 (8) ÅT = 293 K
V = 1434.9 (10) Å3Block, colourless
Z = 40.40 × 0.30 × 0.25 mm
Data collection top
Enraf–Nonius KappaCCD
diffractometer		1847 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 28.6°, θmin = 3.2°
Detector resolution: 9 pixels mm-1h = −10→11
ϕ and ω scansk = −12→12
8829 measured reflectionsl = −22→23
2054 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0447P)2 + 0.2149P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.101(Δ/σ)max = 0.01
S = 1.11Δρmax = 0.21 e Å−3
2054 reflectionsΔρmin = −0.17 e Å−3
194 parameters
Crystal data top
C15H22O5V = 1434.9 (10) Å3
Mr = 282.33Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.417 (4) ŵ = 0.10 mm−1
b = 9.919 (3) ÅT = 293 K
c = 17.187 (8) Å0.40 × 0.30 × 0.25 mm
Data collection top
Enraf–Nonius KappaCCD
diffractometer		1847 reflections with I > 2σ(I)
8829 measured reflectionsRint = 0.038
2054 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.21 e Å−3
2054 reflectionsΔρmin = −0.17 e Å−3
194 parameters
Special details top

Experimental. Centaurea musimomum L.was collected in June 2002 in Didouche Mourad (Constantine) Algeria and authenticated by Professor Nadra Khalfallah (Quezel & Santa, 1963). A voucher specimen was deposited in the herbarium of the Department of Nature and Life Sciences, Mentouri University, Constantine. Air-dried leaves (339 g) and air-dried flowers (202 g) were separately macerated, three times for 24 h, at room temperature with a mixture of methanol-water (70:30). The filtrates were concentrated and successsively extracted with petrol, chloroform, ethyl acetate and n-butanol. The ethyl acetate phases yield, after drying and solvent evaporation 10.8 g and 4.9 g respectively. Analysis by TLC on silica-gel plates showed no significant differences between the leaves and the flowers extract and they were mixed. A part (13 g) of the combined extract was chromatographed on a 230–400 mesh silica gel (325 g) column with chloroform-acetone mixtures of increasing polarity as elution solvents to yield the title compound: cynaratriol together with other related sesquiterpene lactones.

The molecular formula C~15~ H~22~ O~5~ was deduced from its high resolution MS spectrum which shows a molecular ion at m/z=280.1329. The ^13Ĉ and ^1ĤNMR data are very similar to those of 4β,15-Dihydro-3-dehydrosolstiatilin A (Medjroubi et al., 2003), the differences arises from the replacement of the oxo group at C3 by an hydroxyl group.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1−0.0496 (3)0.33998 (17)0.44392 (9)0.0577 (5)
H1O−0.107 (5)0.379 (4)0.469 (2)0.108 (15)*
O2−0.14872 (16)0.42543 (15)0.15121 (8)0.0379 (3)
O3−0.30157 (18)0.45503 (19)0.04747 (9)0.0540 (4)
O4−0.0339 (3)0.60068 (15)−0.01439 (9)0.0521 (5)
H4O−0.020 (4)0.673 (3)0.0102 (18)0.070 (9)*
O50.0257 (3)0.25259 (15)0.02916 (9)0.0536 (5)
H5O0.074 (3)0.190 (3)0.0041 (15)0.052 (7)*
C10.2066 (2)0.4743 (2)0.28881 (12)0.0388 (5)
H10.23760.56130.31120.047*
C20.1768 (3)0.3797 (2)0.35773 (12)0.0472 (5)
H2A0.17270.28630.34120.057*
H2B0.2580.38980.39730.057*
C30.0174 (3)0.4275 (2)0.38653 (11)0.0422 (5)
H30.02920.51790.40880.051*
C4−0.0815 (2)0.4369 (2)0.31246 (11)0.0358 (4)
H4−0.10960.34530.29620.043*
C50.0359 (2)0.49556 (18)0.25231 (10)0.0308 (4)
H50.01630.59260.24780.037*
C60.0215 (2)0.43313 (19)0.17180 (10)0.0289 (4)
H60.06750.34240.17210.035*
C70.0949 (2)0.51598 (19)0.10596 (10)0.0326 (4)
H70.08130.61110.120.039*
C80.2719 (3)0.4939 (3)0.09333 (13)0.0476 (5)
H8A0.30760.54930.05020.057*
H8B0.29060.40030.07980.057*
C90.3682 (3)0.5293 (3)0.16608 (14)0.0542 (6)
H9A0.48040.52680.15330.065*
H9B0.34250.62060.18190.065*
C100.3375 (2)0.4353 (2)0.23343 (13)0.0461 (5)
C11−0.0147 (2)0.48927 (19)0.03617 (10)0.0346 (4)
C12−0.1702 (2)0.4552 (2)0.07626 (11)0.0373 (4)
C130.0313 (3)0.37152 (19)−0.01605 (12)0.0422 (5)
H13A−0.0420.3648−0.05940.051*
H13B0.13750.3848−0.03660.051*
C140.4258 (3)0.3269 (3)0.24326 (18)0.0706 (8)
H14A0.40850.27090.28580.085*
H14B0.50550.30650.20770.085*
C15−0.2339 (3)0.5172 (3)0.32204 (14)0.0529 (6)
H15B−0.20880.60690.33910.079*
H15A−0.30050.47420.360.079*
H15C−0.28870.52130.27310.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0988 (15)0.0417 (8)0.0325 (8)0.0184 (9)0.0167 (9)0.0085 (6)
O20.0299 (6)0.0527 (8)0.0313 (7)−0.0041 (6)−0.0031 (6)−0.0017 (6)
O30.0408 (8)0.0734 (11)0.0476 (9)0.0025 (8)−0.0155 (7)−0.0084 (8)
O40.0908 (13)0.0333 (7)0.0323 (8)−0.0003 (8)−0.0162 (9)0.0022 (6)
O50.0823 (13)0.0323 (7)0.0462 (9)0.0082 (8)0.0134 (9)−0.0018 (7)
C10.0402 (10)0.0410 (10)0.0353 (10)−0.0029 (8)−0.0124 (8)−0.0052 (8)
C20.0600 (13)0.0485 (11)0.0330 (11)0.0082 (11)−0.0148 (10)−0.0014 (9)
C30.0679 (14)0.0321 (9)0.0268 (9)0.0063 (10)−0.0025 (10)−0.0004 (7)
C40.0454 (10)0.0334 (9)0.0286 (9)−0.0013 (9)0.0015 (8)0.0000 (7)
C50.0344 (9)0.0299 (8)0.0280 (8)0.0005 (7)−0.0039 (7)−0.0003 (7)
C60.0264 (8)0.0318 (8)0.0286 (9)0.0000 (7)−0.0024 (7)−0.0003 (7)
C70.0358 (9)0.0345 (9)0.0276 (9)−0.0040 (8)−0.0006 (8)−0.0009 (7)
C80.0375 (11)0.0649 (14)0.0403 (11)−0.0067 (11)0.0058 (9)−0.0016 (11)
C90.0317 (10)0.0745 (16)0.0563 (14)−0.0137 (11)0.0001 (10)−0.0048 (12)
C100.0295 (9)0.0611 (12)0.0476 (12)−0.0039 (10)−0.0109 (9)−0.0071 (10)
C110.0464 (10)0.0300 (8)0.0272 (9)0.0007 (8)−0.0045 (8)−0.0004 (7)
C120.0395 (10)0.0387 (10)0.0338 (10)0.0014 (9)−0.0068 (8)−0.0092 (8)
C130.0572 (13)0.0373 (10)0.0320 (10)0.0021 (10)0.0015 (10)−0.0045 (8)
C140.0441 (13)0.088 (2)0.0794 (19)0.0196 (15)−0.0051 (14)−0.0036 (16)
C150.0459 (12)0.0723 (15)0.0405 (12)0.0069 (12)0.0112 (10)0.0035 (11)
Geometric parameters (Å, º) top
O1—C31.430 (3)C5—H50.98
O1—H1O0.76 (4)C6—C71.529 (3)
O2—C121.334 (2)C6—H60.98
O2—C61.477 (2)C7—C81.522 (3)
O3—C121.211 (2)C7—C111.536 (3)
O4—C111.415 (2)C7—H70.98
O4—H4O0.84 (3)C8—C91.531 (3)
O5—C131.413 (3)C8—H8A0.97
O5—H5O0.86 (3)C8—H8B0.97
C1—C101.507 (3)C9—C101.509 (3)
C1—C21.531 (3)C9—H9A0.97
C1—C51.582 (3)C9—H9B0.97
C1—H10.98C10—C141.317 (4)
C2—C31.507 (3)C11—C121.517 (3)
C2—H2A0.97C11—C131.523 (3)
C2—H2B0.97C13—H13A0.97
C3—C41.524 (3)C13—H13B0.97
C3—H30.98C14—H14A0.93
C4—C151.519 (3)C14—H14B0.93
C4—C51.544 (3)C15—H15B0.96
C4—H40.98C15—H15A0.96
C5—C61.521 (2)C15—H15C0.96
C3—O1—H1O110 (3)C8—C7—H7106.7
C12—O2—C6110.58 (15)C6—C7—H7106.7
C11—O4—H4O110 (2)C11—C7—H7106.7
C13—O5—H5O108.2 (17)C7—C8—C9111.64 (18)
C10—C1—C2116.82 (18)C7—C8—H8A109.3
C10—C1—C5116.63 (16)C9—C8—H8A109.3
C2—C1—C5103.87 (16)C7—C8—H8B109.3
C10—C1—H1106.2C9—C8—H8B109.3
C2—C1—H1106.2H8A—C8—H8B108
C5—C1—H1106.2C10—C9—C8113.23 (19)
C3—C2—C1101.96 (17)C10—C9—H9A108.9
C3—C2—H2A111.4C8—C9—H9A108.9
C1—C2—H2A111.4C10—C9—H9B108.9
C3—C2—H2B111.4C8—C9—H9B108.9
C1—C2—H2B111.4H9A—C9—H9B107.7
H2A—C2—H2B109.2C14—C10—C1122.8 (2)
O1—C3—C2112.74 (18)C14—C10—C9120.4 (2)
O1—C3—C4113.45 (19)C1—C10—C9116.8 (2)
C2—C3—C4103.36 (16)O4—C11—C12110.76 (17)
O1—C3—H3109O4—C11—C13105.43 (15)
C2—C3—H3109C12—C11—C13108.42 (17)
C4—C3—H3109O4—C11—C7114.41 (16)
C15—C4—C3113.75 (17)C12—C11—C7101.65 (15)
C15—C4—C5114.55 (17)C13—C11—C7116.10 (17)
C3—C4—C5103.48 (16)O3—C12—O2121.20 (19)
C15—C4—H4108.3O3—C12—C11127.03 (18)
C3—C4—H4108.3O2—C12—C11111.76 (16)
C5—C4—H4108.3O5—C13—C11107.92 (16)
C6—C5—C4113.89 (15)O5—C13—H13A110.1
C6—C5—C1112.26 (15)C11—C13—H13A110.1
C4—C5—C1105.39 (15)O5—C13—H13B110.1
C6—C5—H5108.4C11—C13—H13B110.1
C4—C5—H5108.4H13A—C13—H13B108.4
C1—C5—H5108.4C10—C14—H14A120
O2—C6—C5108.44 (14)C10—C14—H14B120
O2—C6—C7104.02 (14)H14A—C14—H14B120
C5—C6—C7114.98 (15)C4—C15—H15B109.5
O2—C6—H6109.7C4—C15—H15A109.5
C5—C6—H6109.7H15B—C15—H15A109.5
C7—C6—H6109.7C4—C15—H15C109.5
C8—C7—C6115.08 (17)H15B—C15—H15C109.5
C8—C7—C11116.86 (17)H15A—C15—H15C109.5
C6—C7—C11104.04 (15)
C10—C1—C2—C3−165.75 (17)C6—C7—C8—C9−59.8 (3)
C5—C1—C2—C3−35.80 (18)C11—C7—C8—C9177.73 (18)
C1—C2—C3—O1170.47 (17)C7—C8—C9—C1067.0 (3)
C1—C2—C3—C447.57 (19)C2—C1—C10—C14−1.2 (3)
O1—C3—C4—C1572.7 (2)C5—C1—C10—C14−124.9 (2)
C2—C3—C4—C15−164.87 (18)C2—C1—C10—C9−179.27 (18)
O1—C3—C4—C5−162.39 (16)C5—C1—C10—C957.1 (2)
C2—C3—C4—C5−39.96 (19)C8—C9—C10—C1491.2 (3)
C15—C4—C5—C6−95.3 (2)C8—C9—C10—C1−90.7 (2)
C3—C4—C5—C6140.34 (15)C8—C7—C11—O4−86.5 (2)
C15—C4—C5—C1141.25 (19)C6—C7—C11—O4145.49 (17)
C3—C4—C5—C116.86 (18)C8—C7—C11—C12154.14 (18)
C10—C1—C5—C617.1 (2)C6—C7—C11—C1226.08 (18)
C2—C1—C5—C6−112.97 (17)C8—C7—C11—C1336.7 (3)
C10—C1—C5—C4141.60 (18)C6—C7—C11—C13−91.3 (2)
C2—C1—C5—C411.53 (19)C6—O2—C12—O3−179.83 (19)
C12—O2—C6—C5140.81 (16)C6—O2—C12—C11−0.8 (2)
C12—O2—C6—C718.0 (2)O4—C11—C12—O340.5 (3)
C4—C5—C6—O245.5 (2)C13—C11—C12—O3−74.7 (3)
C1—C5—C6—O2165.20 (15)C7—C11—C12—O3162.5 (2)
C4—C5—C6—C7161.46 (16)O4—C11—C12—O2−138.44 (16)
C1—C5—C6—C7−78.87 (19)C13—C11—C12—O2106.34 (18)
O2—C6—C7—C8−156.38 (16)C7—C11—C12—O2−16.5 (2)
C5—C6—C7—C885.2 (2)O4—C11—C13—O5−170.20 (19)
O2—C6—C7—C11−27.24 (18)C12—C11—C13—O5−51.6 (2)
C5—C6—C7—C11−145.67 (15)C7—C11—C13—O562.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O1i0.84 (3)1.93 (3)2.756 (2)169 (3)
O5—H5O···O3ii0.86 (3)1.99 (3)2.844 (2)176 (3)
O1—H1O···O3iii0.76 (4)2.26 (4)2.978 (3)159 (4)
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x+1/2, −y+1/2, −z; (iii) −x−1/2, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H22O5
Mr282.33
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)8.417 (4), 9.919 (3), 17.187 (8)
V (Å3)1434.9 (10)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.40 × 0.30 × 0.25
Data collection
DiffractometerEnraf–Nonius KappaCCD
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		8829, 2054, 1847
Rint0.038
(sin θ/λ)max (Å−1)0.674
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.101, 1.11
No. of reflections2054
No. of parameters194
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.21, −0.17

Computer programs: COLLECT (Nonius, 2000), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4O···O1i0.84 (3)1.93 (3)2.756 (2)169 (3)
O5—H5O···O3ii0.86 (3)1.99 (3)2.844 (2)176 (3)
O1—H1O···O3iii0.76 (4)2.26 (4)2.978 (3)159 (4)
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x+1/2, −y+1/2, −z; (iii) −x−1/2, −y+1, z+1/2.
 

Acknowledgements

The authors wish to thank Professor N. Khalfallah of the Nature and Life Sciences Department, Mentorui University of Constantine, Algerie, for the identification of the plant material.

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationGonzález-Platas, J., Ruiz-Pérez, C., González, A. G., Bermejo, J. & Medjroubi, K. (1999). Acta Cryst. C55, 1837–1839.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationHeinz, B. O. von, Thiele, K. & Pretsch, E. (1979). Helv. Chim. Acta, 62, 1289–1297.  Google Scholar
 First citationMedjroubi, K., Benayache, F., Benayache, S., Akkal, S., Khalfallah, N. & Aclinou, P. (1997). Phytochemistry, 45, 1449–1452.  CrossRef CAS Web of Science Google Scholar
 First citationMedjroubi, K., Benayache, F. & Bermejo, J. (2005). Fitoterapia, 76, 744–745.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationMedjroubi, K., Benayache, F., León, F. & Bermejo, J. (2003). Rev. Colombiana Quim., 32, 17-25.  CAS Google Scholar
 First citationNonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOksuz, S., Clark, R. J. & Herz, W. (1993). Phytochem, 33, 1267.  CSD CrossRef Web of Science Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationQuezel, P. & Santa, S. (1963). Nouvelle flore de l'Algérie et des régions désertiques méridionales. Paris, Editions du CNRS.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 8| August 2009| Pages o1867-o1868
doi:10.1107/S1600536809026701
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS