Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C15H24O5, was isolated from the flowers of Parthenium hysterophorus. The crystal structure determination confirms the relative stereochemistry unambiguously. The packing is stabilized by O—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032532/bt6566sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032532/bt6566Isup2.hkl
Contains datablock I

CCDC reference: 262467

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.087
  • Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 27.58 From the CIF: _reflns_number_total 1649 Count of symmetry unique reflns 1758 Completeness (_total/calc) 93.80% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

(3R,6S,6aR,9S,9aS)-6,6a,9-Trihydroxy-3,6,9a- trimethylperhydroazuleno[1,2-b]furan-2-one top
Crystal data top
C15H24O5F(000) = 308
Mr = 284.34Dx = 1.295 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.0046 (8) ÅCell parameters from 3140 reflections
b = 13.1146 (14) Åθ = 6.0–56.0°
c = 8.4316 (9) ŵ = 0.10 mm1
β = 109.753 (2)°T = 273 K
V = 728.97 (14) Å3Needle, colourless
Z = 20.24 × 0.20 × 0.14 mm
Data collection top
Bruker Smart APEX CCD area-detector
diffractometer
1615 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 27.6°, θmin = 2.6°
ω scansh = 89
4433 measured reflectionsk = 1617
1649 independent reflectionsl = 1110
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.072P)2 + 0.603P]
where P = (Fo2 + 2Fc2)/3
1649 reflections(Δ/σ)max < 0.001
187 parametersΔρmax = 0.20 e Å3
1 restraintΔρmin = 0.19 e Å3
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
O30.4154 (3)0.58066 (12)0.1796 (2)0.0464 (4)
H30.40850.61170.26190.070*
O50.7294 (3)0.16126 (12)0.2463 (2)0.0489 (4)
O20.3381 (2)0.38911 (12)0.2134 (2)0.0455 (4)
H20.26800.43890.17210.068*
C80.7567 (3)0.30168 (15)0.0766 (3)0.0343 (4)
H80.67120.28130.03710.041*
C50.5921 (3)0.51511 (14)0.2305 (3)0.0343 (4)
C40.5348 (3)0.42262 (15)0.3212 (3)0.0325 (4)
C90.6494 (3)0.26445 (14)0.1984 (2)0.0336 (4)
H90.50450.25810.13360.040*
O10.6757 (3)0.18300 (13)0.5607 (2)0.0597 (5)
H10.71120.14440.49940.090*
C70.7948 (3)0.41640 (16)0.0705 (3)0.0405 (5)
H7A0.90790.43490.17000.049*
H7B0.83470.43030.02690.049*
C100.8923 (4)0.14212 (19)0.1983 (3)0.0509 (6)
O40.9740 (4)0.06046 (16)0.2231 (3)0.0791 (7)
C10.5594 (4)0.26461 (17)0.4629 (3)0.0441 (5)
H1A0.43080.23750.38640.053*
C140.8909 (3)0.34248 (17)0.4705 (3)0.0411 (5)
H14A0.95630.27810.50630.062*
H14B0.89400.38170.56750.062*
H14C0.96060.37890.40780.062*
C150.6687 (3)0.32442 (14)0.3581 (2)0.0319 (4)
C60.6148 (3)0.48453 (16)0.0614 (3)0.0387 (4)
H6A0.49170.44980.00550.046*
H6B0.62500.54640.00170.046*
C130.7714 (4)0.57862 (17)0.3374 (3)0.0465 (5)
H13A0.78600.63750.27470.070*
H13B0.89290.53840.36660.070*
H13C0.74850.60010.43830.070*
C110.9483 (3)0.23610 (18)0.1232 (3)0.0447 (5)
H111.05490.27150.21250.054*
C30.5146 (4)0.44758 (18)0.4943 (3)0.0470 (5)
H3A0.62750.48910.56170.056*
H3B0.38910.48380.48000.056*
C121.0300 (4)0.2139 (2)0.0201 (4)0.0595 (7)
H12A1.14590.16980.02000.089*
H12B1.06900.27670.05910.089*
H12C0.92660.18130.11120.089*
C20.5153 (5)0.3433 (2)0.5783 (3)0.0573 (7)
H2A0.61900.34140.68890.069*
H2B0.38470.33020.59050.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0591 (9)0.0382 (7)0.0431 (8)0.0145 (7)0.0188 (8)0.0023 (7)
O50.0686 (10)0.0285 (7)0.0517 (9)0.0025 (7)0.0229 (8)0.0006 (7)
O20.0317 (7)0.0441 (8)0.0583 (10)0.0038 (6)0.0120 (7)0.0017 (7)
C80.0359 (8)0.0355 (9)0.0333 (10)0.0005 (7)0.0141 (8)0.0044 (8)
C50.0426 (10)0.0272 (8)0.0354 (10)0.0012 (7)0.0163 (9)0.0013 (7)
C40.0343 (8)0.0299 (8)0.0349 (10)0.0032 (7)0.0139 (8)0.0004 (7)
C90.0361 (9)0.0272 (8)0.0372 (10)0.0022 (7)0.0121 (8)0.0002 (7)
O10.0922 (14)0.0391 (9)0.0554 (11)0.0027 (9)0.0350 (10)0.0167 (8)
C70.0476 (10)0.0385 (10)0.0435 (12)0.0050 (9)0.0259 (10)0.0016 (8)
C100.0576 (13)0.0433 (12)0.0454 (13)0.0106 (10)0.0090 (11)0.0071 (10)
O40.0967 (16)0.0567 (12)0.0779 (15)0.0365 (12)0.0215 (13)0.0056 (11)
C10.0566 (12)0.0377 (10)0.0442 (12)0.0062 (9)0.0249 (11)0.0080 (9)
C140.0403 (10)0.0411 (11)0.0360 (11)0.0005 (8)0.0054 (9)0.0008 (9)
C150.0371 (8)0.0283 (8)0.0314 (9)0.0032 (7)0.0129 (8)0.0030 (7)
C60.0525 (11)0.0330 (9)0.0342 (11)0.0000 (8)0.0193 (9)0.0046 (8)
C130.0577 (13)0.0340 (10)0.0502 (13)0.0115 (10)0.0215 (11)0.0042 (9)
C110.0369 (9)0.0471 (12)0.0470 (13)0.0035 (9)0.0102 (9)0.0143 (10)
C30.0636 (13)0.0408 (11)0.0469 (12)0.0005 (10)0.0321 (11)0.0008 (10)
C120.0480 (13)0.0660 (16)0.0709 (17)0.0009 (11)0.0285 (12)0.0253 (14)
C20.0798 (18)0.0538 (14)0.0528 (14)0.0035 (12)0.0415 (14)0.0104 (12)
Geometric parameters (Å, º) top
O3—C51.448 (2)C10—C111.497 (4)
O3—H30.8200C1—C21.520 (3)
O5—C101.357 (3)C1—C151.562 (3)
O5—C91.468 (2)C1—H1A0.9800
O2—C41.439 (2)C14—C151.543 (3)
O2—H20.8200C14—H14A0.9600
C8—C111.529 (3)C14—H14B0.9600
C8—C71.532 (3)C14—H14C0.9600
C8—C91.543 (3)C6—H6A0.9700
C8—H80.9800C6—H6B0.9700
C5—C131.523 (3)C13—H13A0.9600
C5—C61.540 (3)C13—H13B0.9600
C5—C41.558 (3)C13—H13C0.9600
C4—C31.548 (3)C11—C121.530 (3)
C4—C151.561 (3)C11—H110.9800
C9—C151.525 (3)C3—C21.539 (3)
C9—H90.9800C3—H3A0.9700
O1—C11.427 (3)C3—H3B0.9700
O1—H10.8200C12—H12A0.9600
C7—C61.526 (3)C12—H12B0.9600
C7—H7A0.9700C12—H12C0.9600
C7—H7B0.9700C2—H2A0.9700
C10—O41.199 (3)C2—H2B0.9700
C5—O3—H3109.5C15—C14—H14C109.5
C10—O5—C9111.70 (17)H14A—C14—H14C109.5
C4—O2—H2109.5H14B—C14—H14C109.5
C11—C8—C7114.41 (17)C9—C15—C14113.06 (16)
C11—C8—C9103.50 (17)C9—C15—C1109.04 (15)
C7—C8—C9117.58 (16)C14—C15—C1108.37 (17)
C11—C8—H8106.9C9—C15—C4112.43 (15)
C7—C8—H8106.9C14—C15—C4114.15 (16)
C9—C8—H8106.9C1—C15—C498.65 (15)
O3—C5—C13107.59 (17)C7—C6—C5116.62 (18)
O3—C5—C6103.06 (16)C7—C6—H6A108.1
C13—C5—C6111.59 (16)C5—C6—H6A108.1
O3—C5—C4105.73 (15)C7—C6—H6B108.1
C13—C5—C4115.67 (17)C5—C6—H6B108.1
C6—C5—C4112.11 (15)H6A—C6—H6B107.3
O2—C4—C3106.68 (16)C5—C13—H13A109.5
O2—C4—C5106.15 (16)C5—C13—H13B109.5
C3—C4—C5114.79 (17)H13A—C13—H13B109.5
O2—C4—C15104.85 (15)C5—C13—H13C109.5
C3—C4—C15103.13 (16)H13A—C13—H13C109.5
C5—C4—C15120.19 (14)H13B—C13—H13C109.5
O5—C9—C15108.70 (15)C10—C11—C8103.84 (17)
O5—C9—C8104.38 (15)C10—C11—C12113.5 (2)
C15—C9—C8120.44 (16)C8—C11—C12115.7 (2)
O5—C9—H9107.6C10—C11—H11107.8
C15—C9—H9107.6C8—C11—H11107.8
C8—C9—H9107.6C12—C11—H11107.8
C1—O1—H1109.5C2—C3—C4104.99 (18)
C6—C7—C8115.23 (16)C2—C3—H3A110.7
C6—C7—H7A108.5C4—C3—H3A110.7
C8—C7—H7A108.5C2—C3—H3B110.7
C6—C7—H7B108.5C4—C3—H3B110.7
C8—C7—H7B108.5H3A—C3—H3B108.8
H7A—C7—H7B107.5C11—C12—H12A109.5
O4—C10—O5120.9 (3)C11—C12—H12B109.5
O4—C10—C11129.1 (2)H12A—C12—H12B109.5
O5—C10—C11109.92 (18)C11—C12—H12C109.5
O1—C1—C2109.81 (19)H12A—C12—H12C109.5
O1—C1—C15114.24 (18)H12B—C12—H12C109.5
C2—C1—C15105.40 (18)C1—C2—C3106.17 (17)
O1—C1—H1A109.1C1—C2—H2A110.5
C2—C1—H1A109.1C3—C2—H2A110.5
C15—C1—H1A109.1C1—C2—H2B110.5
C15—C14—H14A109.5C3—C2—H2B110.5
C15—C14—H14B109.5H2A—C2—H2B108.7
H14A—C14—H14B109.5
O3—C5—C4—O247.78 (19)O1—C1—C15—C4162.40 (18)
C13—C5—C4—O2166.71 (17)C2—C1—C15—C441.8 (2)
C6—C5—C4—O263.80 (19)O2—C4—C15—C948.40 (18)
O3—C5—C4—C369.8 (2)C3—C4—C15—C9159.91 (16)
C13—C5—C4—C349.1 (2)C5—C4—C15—C970.8 (2)
C6—C5—C4—C3178.62 (18)O2—C4—C15—C14178.89 (15)
O3—C5—C4—C15166.27 (16)C3—C4—C15—C1469.59 (19)
C13—C5—C4—C1574.8 (2)C5—C4—C15—C1459.7 (2)
C6—C5—C4—C1554.7 (2)O2—C4—C15—C166.42 (18)
C10—O5—C9—C15117.59 (19)C3—C4—C15—C145.09 (19)
C10—O5—C9—C812.1 (2)C5—C4—C15—C1174.42 (17)
C11—C8—C9—O522.9 (2)C8—C7—C6—C587.2 (2)
C7—C8—C9—O5150.16 (18)O3—C5—C6—C7178.24 (17)
C11—C8—C9—C1599.37 (19)C13—C5—C6—C763.1 (2)
C7—C8—C9—C1527.8 (3)C4—C5—C6—C768.5 (2)
C11—C8—C7—C6167.57 (18)O4—C10—C11—C8163.5 (3)
C9—C8—C7—C645.8 (3)O5—C10—C11—C819.2 (3)
C9—O5—C10—O4178.0 (2)O4—C10—C11—C1237.0 (4)
C9—O5—C10—C114.4 (3)O5—C10—C11—C12145.7 (2)
O5—C9—C15—C1465.2 (2)C7—C8—C11—C10154.41 (18)
C8—C9—C15—C1455.0 (2)C9—C8—C11—C1025.2 (2)
O5—C9—C15—C155.4 (2)C7—C8—C11—C1280.5 (2)
C8—C9—C15—C1175.59 (18)C9—C8—C11—C12150.3 (2)
O5—C9—C15—C4163.72 (14)O2—C4—C3—C277.4 (2)
C8—C9—C15—C476.1 (2)C5—C4—C3—C2165.29 (19)
O1—C1—C15—C980.2 (2)C15—C4—C3—C232.7 (2)
C2—C1—C15—C9159.20 (19)O1—C1—C2—C3146.2 (2)
O1—C1—C15—C1443.3 (2)C15—C1—C2—C322.7 (3)
C2—C1—C15—C1477.4 (2)C4—C3—C2—C16.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.822.012.818 (2)167
O2—H2···O30.822.122.605 (2)118
O1—H1···O50.822.192.815 (2)133
C6—H6A···O20.972.562.940 (3)104
C9—H9···O20.982.302.762 (2)108
C11—H11···O2ii0.982.513.265 (3)134
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x+1, y, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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