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Single crystals of senecio lactone, C8H8O4, isolated from Senecio scandens Buch–Ham, were obtained from an acetone solution. In the crystal structure, mol­ecules are linked to each other by inter­molecular O—H...O hydrogen bonds involving a ketone group and the hydroxyl group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042868/bh6047sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042868/bh6047Isup2.hkl
Contains datablock I

CCDC reference: 298669

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.055
  • wR factor = 0.147
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ... 1.19 PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95 PLAT432_ALERT_2_B Short Inter X...Y Contact O2 .. C6 .. 2.91 Ang.
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C8 H8 O4
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALE (Otwinowski & Minor, 1997); data reduction: SCALE; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLUTON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(3aRS,7aRS)-3a-Hydroxy-3,3a,7,7a-tetrahydrobenzofuran-2,6-dione top
Crystal data top
C8H8O4Dx = 1.524 Mg m3
Mr = 168.15Melting point = 382–384 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.7870 (14) ÅCell parameters from 2341 reflections
b = 10.711 (2) Åθ = 2.8–25.0°
c = 10.311 (2) ŵ = 0.12 mm1
β = 102.06 (3)°T = 295 K
V = 733.0 (3) Å3Plate, colourless
Z = 40.50 × 0.40 × 0.10 mm
F(000) = 352
Data collection top
MAC DIP-2030K
diffractometer
1533 reflections with I > 2σ(I)
Radiation source: rotating-anodeRint = 0.032
Graphite monochromatorθmax = 25.0°, θmin = 2.8°
ω scansh = 08
2341 measured reflectionsk = 1213
1534 independent reflectionsl = 1312
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)] = 0.055H-atom parameters constrained
wR(F2) = 0.147 w = 1/[σ2(Fo2) + (0.0589P)2 + 0.3161P]
where P = (Fo2 + 2Fc2)/3
S = 1.27(Δ/σ)max < 0.001
1534 reflectionsΔρmax = 0.24 e Å3
110 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.122 (15)
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
O10.1607 (2)0.06981 (15)0.60570 (15)0.0488 (4)
O20.4950 (2)0.08404 (16)0.63864 (16)0.0562 (5)
O30.1067 (2)0.32862 (14)0.67556 (16)0.0498 (4)
H3A0.00400.36260.65850.075*
O40.2691 (2)0.02618 (16)0.90892 (16)0.0546 (5)
C10.3425 (3)0.10692 (19)0.6760 (2)0.0424 (5)
C20.3156 (3)0.17683 (19)0.7978 (2)0.0415 (5)
H2A0.40860.24640.81700.050*
H2B0.33360.12240.87460.050*
C30.0981 (3)0.22170 (17)0.75689 (19)0.0378 (5)
C40.0063 (3)0.2518 (2)0.8676 (2)0.0421 (5)
H4A0.01610.32970.90780.051*
C50.1292 (3)0.17322 (19)0.9117 (2)0.0433 (5)
H5A0.19450.19990.97760.052*
C60.1652 (3)0.04606 (19)0.8599 (2)0.0421 (5)
C70.0591 (3)0.00511 (19)0.7529 (2)0.0446 (5)
H7A0.14700.05110.69350.054*
H7B0.06050.04140.79350.054*
C80.0026 (3)0.1112 (2)0.6716 (2)0.0412 (5)
H8A0.11430.13980.60560.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0446 (8)0.0609 (9)0.0429 (8)0.0028 (7)0.0139 (6)0.0098 (7)
O20.0484 (9)0.0675 (11)0.0580 (10)0.0130 (7)0.0235 (7)0.0091 (8)
O30.0492 (8)0.0429 (8)0.0612 (9)0.0076 (6)0.0205 (7)0.0153 (7)
O40.0534 (9)0.0562 (9)0.0545 (9)0.0137 (7)0.0122 (7)0.0086 (7)
C10.0422 (10)0.0444 (10)0.0425 (10)0.0056 (8)0.0135 (8)0.0079 (8)
C20.0379 (9)0.0436 (10)0.0432 (10)0.0004 (8)0.0091 (8)0.0017 (8)
C30.0385 (9)0.0354 (9)0.0409 (9)0.0004 (7)0.0116 (7)0.0032 (7)
C40.0439 (10)0.0395 (9)0.0444 (10)0.0013 (8)0.0129 (8)0.0035 (8)
C50.0434 (10)0.0466 (11)0.0432 (10)0.0024 (8)0.0161 (8)0.0013 (8)
C60.0368 (9)0.0435 (10)0.0444 (10)0.0009 (8)0.0051 (8)0.0057 (8)
C70.0424 (10)0.0388 (10)0.0529 (11)0.0021 (8)0.0108 (9)0.0058 (9)
C80.0365 (9)0.0477 (11)0.0395 (9)0.0038 (8)0.0083 (7)0.0034 (8)
Geometric parameters (Å, º) top
O1—C11.354 (3)C3—C81.535 (3)
O1—C81.454 (2)C4—C51.330 (3)
O2—C11.203 (2)C4—H4A0.9300
O3—C31.428 (2)C5—C61.465 (3)
O3—H3A0.8200C5—H5A0.9300
O4—C61.225 (2)C6—C71.503 (3)
C1—C21.506 (3)C7—C81.522 (3)
C2—C31.526 (3)C7—H7A0.9700
C2—H2A0.9700C7—H7B0.9700
C2—H2B0.9700C8—H8A0.9800
C3—C41.500 (3)
C1—O1—C8109.83 (15)C3—C4—H4A118.2
C3—O3—H3A109.5C4—C5—C6122.18 (18)
O2—C1—O1121.2 (2)C4—C5—H5A118.9
O2—C1—C2129.1 (2)C6—C5—H5A118.9
O1—C1—C2109.70 (16)O4—C6—C5120.22 (19)
C1—C2—C3101.82 (16)O4—C6—C7121.59 (19)
C1—C2—H2A111.4C5—C6—C7118.04 (17)
C3—C2—H2A111.4C6—C7—C8114.55 (17)
C1—C2—H2B111.4C6—C7—H7A108.6
C3—C2—H2B111.4C8—C7—H7A108.6
H2A—C2—H2B109.3C6—C7—H7B108.6
O3—C3—C4111.02 (15)C8—C7—H7B108.6
O3—C3—C2105.02 (15)H7A—C7—H7B107.6
C4—C3—C2116.16 (17)O1—C8—C7110.18 (17)
O3—C3—C8110.27 (16)O1—C8—C3103.77 (15)
C4—C3—C8113.06 (16)C7—C8—C3113.09 (17)
C2—C3—C8100.60 (15)O1—C8—H8A109.9
C5—C4—C3123.65 (19)C7—C8—H8A109.9
C5—C4—H4A118.2C3—C8—H8A109.9
C8—O1—C1—O2179.06 (19)O4—C6—C7—C8160.35 (19)
C8—O1—C1—C20.4 (2)C5—C6—C7—C824.1 (3)
O2—C1—C2—C3156.0 (2)C1—O1—C8—C798.59 (19)
O1—C1—C2—C323.4 (2)C1—O1—C8—C322.8 (2)
C1—C2—C3—O379.57 (18)C6—C7—C8—O1159.93 (16)
C1—C2—C3—C4157.36 (16)C6—C7—C8—C344.3 (2)
C1—C2—C3—C834.95 (18)O3—C3—C8—O174.90 (18)
O3—C3—C4—C5142.3 (2)C4—C3—C8—O1160.15 (16)
C2—C3—C4—C597.8 (2)C2—C3—C8—O135.60 (18)
C8—C3—C4—C517.8 (3)O3—C3—C8—C7165.73 (15)
C3—C4—C5—C63.4 (3)C4—C3—C8—C740.8 (2)
C4—C5—C6—O4175.3 (2)C2—C3—C8—C783.77 (19)
C4—C5—C6—C70.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O4i0.821.962.756 (2)165
Symmetry code: (i) x+1/2, y1/2, z3/2.
 

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