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The title compound, (1R,3aS,6aS,9S)-(+)-α,3a,7-trimethyl-5-oxo-1,4-ethano­perhydro­penta­lene-1,8-carbolactone, C15H18O3, is the enol lactone of (−)-isosantonic acid, and a diastereomer of (+)-parasantonide. It is a skeletally rigid tetra­cyclic sesquiterpene derived from (−)-α-santonin, an anthelminthic obtained from various species of Artemisia. Molecules are linked by C—H...O close intermolecular contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007982/tk2133sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007982/tk2133Isup2.hkl
Contains datablock I

CCDC reference: 640506

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.025
  • wR factor = 0.060
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5878 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 65.00 Deg. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C12
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 65.00 From the CIF: _reflns_number_total 2023 Count of symmetry unique reflns 1239 Completeness (_total/calc) 163.28% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 784 Fraction of Friedel pairs measured 0.633 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6A = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 5 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 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(1R,3aS,6aS,9S)-(+)-α,3a,7-trimethyl-5-oxo-1,4-ethanoperhydropentalene- 1,8-carbolactone top
Crystal data top
C15H18O3Dx = 1.316 Mg m3
Mr = 246.29Melting point: 403 K
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 4812 reflections
a = 7.8611 (2) Åθ = 3.4–65.0°
b = 12.0650 (3) ŵ = 0.73 mm1
c = 13.1038 (4) ÅT = 100 K
V = 1242.82 (6) Å3Prism, colourless
Z = 40.24 × 0.20 × 0.10 mm
F(000) = 528
Data collection top
Bruker SMART APEX II CCD area-detector
diffractometer
2023 independent reflections
Radiation source: fine-focus sealed tube2021 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
φ and ω scansθmax = 65.0°, θmin = 5.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 99
Tmin = 0.844, Tmax = 0.930k = 1114
4823 measured reflectionsl = 1115
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.025 w = 1/[σ2(Fo2) + (0.0243P)2 + 0.3284P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.060(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.15 e Å3
2023 reflectionsΔρmin = 0.10 e Å3
167 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0021 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 783 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.12 (18)
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
O10.88853 (12)0.84461 (7)0.90876 (7)0.0250 (2)
C11.01164 (16)0.69781 (10)0.81328 (10)0.0208 (3)
O20.52538 (11)0.65202 (8)0.63889 (7)0.0278 (2)
C21.17714 (16)0.73978 (11)0.76301 (11)0.0239 (3)
H2A1.21150.81230.79170.029*
H2B1.27100.68610.77280.029*
O31.00221 (13)0.81354 (9)1.06220 (7)0.0349 (3)
C3A0.96813 (16)0.68073 (10)0.63582 (9)0.0210 (3)
C31.13061 (16)0.75048 (11)0.64964 (11)0.0237 (3)
H3A1.22360.72180.60610.028*
H3B1.10920.82890.63150.028*
C40.80057 (15)0.74877 (11)0.64201 (11)0.0208 (3)
H40.77370.78860.57710.025*
C50.67149 (16)0.65834 (11)0.66735 (10)0.0218 (3)
C6A0.95009 (16)0.61074 (10)0.73507 (10)0.0201 (3)
H6A1.02680.54470.73380.024*
C60.76184 (17)0.57606 (11)0.73777 (10)0.0229 (3)
H6B0.74770.49920.71260.027*
H6C0.71610.58080.80800.027*
C70.79081 (15)0.82362 (10)0.73554 (10)0.0209 (3)
C80.88641 (17)0.79259 (10)0.81351 (10)0.0215 (3)
C91.03550 (17)0.67341 (11)0.92759 (10)0.0247 (3)
H91.15900.66070.94180.030*
C100.98048 (17)0.78150 (11)0.97702 (10)0.0255 (3)
C110.93179 (19)0.57825 (12)0.97376 (11)0.0325 (3)
H11A0.95700.57231.04680.049*
H11B0.96190.50870.93970.049*
H11C0.81020.59300.96430.049*
C120.66081 (17)0.91498 (11)0.73617 (11)0.0264 (3)
H12A0.54680.88310.72920.040*
H12B0.68260.96550.67910.040*
H12C0.66830.95590.80060.040*
C130.96969 (18)0.61192 (11)0.53816 (10)0.0256 (3)
H13A0.97600.66140.47890.038*
H13B0.86540.56770.53430.038*
H13C1.06870.56250.53850.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0240 (5)0.0255 (5)0.0255 (5)0.0004 (4)0.0008 (4)0.0043 (4)
C10.0176 (6)0.0195 (6)0.0252 (6)0.0004 (5)0.0002 (5)0.0029 (5)
O20.0185 (5)0.0297 (5)0.0352 (5)0.0019 (4)0.0020 (4)0.0017 (4)
C20.0182 (6)0.0214 (6)0.0322 (7)0.0008 (5)0.0002 (6)0.0004 (6)
O30.0354 (6)0.0431 (6)0.0262 (5)0.0033 (5)0.0022 (4)0.0058 (5)
C3A0.0193 (6)0.0201 (6)0.0236 (6)0.0022 (5)0.0001 (6)0.0011 (5)
C30.0178 (6)0.0241 (7)0.0291 (7)0.0011 (5)0.0031 (6)0.0037 (6)
C40.0177 (6)0.0213 (7)0.0233 (6)0.0014 (5)0.0011 (5)0.0015 (6)
C50.0203 (6)0.0209 (6)0.0242 (6)0.0004 (5)0.0036 (5)0.0069 (5)
C6A0.0173 (6)0.0177 (6)0.0254 (6)0.0022 (5)0.0017 (5)0.0004 (5)
C60.0206 (6)0.0196 (6)0.0285 (7)0.0033 (5)0.0003 (6)0.0014 (5)
C70.0165 (6)0.0187 (6)0.0277 (7)0.0018 (5)0.0017 (5)0.0009 (5)
C80.0176 (6)0.0204 (6)0.0264 (7)0.0038 (5)0.0038 (5)0.0022 (5)
C90.0201 (6)0.0285 (7)0.0256 (7)0.0002 (6)0.0019 (6)0.0021 (6)
C100.0190 (6)0.0312 (7)0.0263 (7)0.0057 (6)0.0007 (6)0.0006 (6)
C110.0370 (8)0.0332 (8)0.0274 (7)0.0056 (6)0.0021 (6)0.0065 (6)
C120.0222 (7)0.0222 (6)0.0347 (7)0.0016 (5)0.0023 (6)0.0029 (6)
C130.0234 (6)0.0266 (7)0.0268 (7)0.0029 (6)0.0031 (6)0.0008 (6)
Geometric parameters (Å, º) top
O1—C101.3792 (17)C5—C61.5303 (19)
O1—C81.3972 (15)C6A—C61.5383 (17)
C1—C81.5089 (17)C6A—H6A1.0000
C1—C91.5380 (18)C6—H6B0.9900
C1—C21.5437 (17)C6—H6C0.9900
C1—C6A1.5453 (17)C7—C81.3224 (19)
O2—C51.2100 (16)C7—C121.5031 (18)
C2—C31.5354 (19)C9—C101.5190 (19)
C2—H2A0.9900C9—C111.5326 (19)
C2—H2B0.9900C9—H91.0000
O3—C101.1935 (16)C11—H11A0.9800
C3A—C131.5254 (18)C11—H11B0.9800
C3A—C31.5403 (18)C11—H11C0.9800
C3A—C41.5542 (17)C12—H12A0.9800
C3A—C6A1.5571 (17)C12—H12B0.9800
C3—H3A0.9900C12—H12C0.9800
C3—H3B0.9900C13—H13A0.9800
C4—C71.5243 (18)C13—H13B0.9800
C4—C51.5265 (18)C13—H13C0.9800
C4—H41.0000
C10—O1—C8109.73 (10)C5—C6—C6A104.84 (10)
C8—C1—C9102.87 (11)C5—C6—H6B110.8
C8—C1—C2107.58 (10)C6A—C6—H6B110.8
C9—C1—C2112.06 (11)C5—C6—H6C110.8
C8—C1—C6A108.19 (10)C6A—C6—H6C110.8
C9—C1—C6A123.64 (11)H6B—C6—H6C108.9
C2—C1—C6A101.76 (10)C8—C7—C12126.14 (12)
C3—C2—C1103.87 (10)C8—C7—C4115.14 (11)
C3—C2—H2A111.0C12—C7—C4118.24 (11)
C1—C2—H2A111.0C7—C8—O1124.73 (12)
C3—C2—H2B111.0C7—C8—C1125.72 (12)
C1—C2—H2B111.0O1—C8—C1109.54 (11)
H2A—C2—H2B109.0C10—C9—C11108.87 (11)
C13—C3A—C3112.91 (11)C10—C9—C1102.49 (10)
C13—C3A—C4109.76 (10)C11—C9—C1117.58 (11)
C3—C3A—C4114.08 (10)C10—C9—H9109.2
C13—C3A—C6A113.98 (10)C11—C9—H9109.2
C3—C3A—C6A105.88 (10)C1—C9—H9109.2
C4—C3A—C6A99.53 (10)O3—C10—O1120.18 (13)
C2—C3—C3A105.39 (10)O3—C10—C9129.50 (13)
C2—C3—H3A110.7O1—C10—C9110.28 (11)
C3A—C3—H3A110.7C9—C11—H11A109.5
C2—C3—H3B110.7C9—C11—H11B109.5
C3A—C3—H3B110.7H11A—C11—H11B109.5
H3A—C3—H3B108.8C9—C11—H11C109.5
C7—C4—C5102.42 (11)H11A—C11—H11C109.5
C7—C4—C3A113.43 (10)H11B—C11—H11C109.5
C5—C4—C3A101.38 (10)C7—C12—H12A109.5
C7—C4—H4112.9C7—C12—H12B109.5
C5—C4—H4112.9H12A—C12—H12B109.5
C3A—C4—H4112.9C7—C12—H12C109.5
O2—C5—C4127.52 (13)H12A—C12—H12C109.5
O2—C5—C6125.84 (12)H12B—C12—H12C109.5
C4—C5—C6106.63 (10)C3A—C13—H13A109.5
C6—C6A—C1118.10 (10)C3A—C13—H13B109.5
C6—C6A—C3A104.73 (10)H13A—C13—H13B109.5
C1—C6A—C3A99.02 (10)C3A—C13—H13C109.5
C6—C6A—H6A111.3H13A—C13—H13C109.5
C1—C6A—H6A111.3H13B—C13—H13C109.5
C3A—C6A—H6A111.3
C8—C1—C2—C371.76 (12)C1—C6A—C6—C588.90 (13)
C9—C1—C2—C3175.87 (10)C3A—C6A—C6—C520.02 (12)
C6A—C1—C2—C341.85 (12)C5—C4—C7—C884.55 (13)
C1—C2—C3—C3A17.74 (12)C3A—C4—C7—C823.84 (16)
C13—C3A—C3—C2138.07 (11)C5—C4—C7—C1287.95 (13)
C4—C3A—C3—C295.70 (12)C3A—C4—C7—C12163.66 (11)
C6A—C3A—C3—C212.70 (13)C12—C7—C8—O13.8 (2)
C13—C3A—C4—C7177.83 (10)C4—C7—C8—O1175.59 (11)
C3—C3A—C4—C749.98 (14)C12—C7—C8—C1177.43 (12)
C6A—C3A—C4—C762.29 (12)C4—C7—C8—C15.62 (19)
C13—C3A—C4—C573.12 (13)C10—O1—C8—C7170.43 (13)
C3—C3A—C4—C5159.02 (11)C10—O1—C8—C110.61 (14)
C6A—C3A—C4—C546.75 (12)C9—C1—C8—C7160.45 (13)
C7—C4—C5—O297.89 (16)C2—C1—C8—C781.09 (16)
C3A—C4—C5—O2144.75 (13)C6A—C1—C8—C728.14 (17)
C7—C4—C5—C681.48 (11)C9—C1—C8—O120.60 (13)
C3A—C4—C5—C635.89 (13)C2—C1—C8—O197.86 (12)
C8—C1—C6A—C647.28 (14)C6A—C1—C8—O1152.92 (10)
C9—C1—C6A—C672.73 (16)C8—C1—C9—C1021.53 (12)
C2—C1—C6A—C6160.44 (11)C2—C1—C9—C1093.74 (12)
C8—C1—C6A—C3A64.84 (12)C6A—C1—C9—C10143.99 (12)
C9—C1—C6A—C3A175.14 (12)C8—C1—C9—C1197.77 (13)
C2—C1—C6A—C3A48.31 (10)C2—C1—C9—C11146.96 (12)
C13—C3A—C6A—C675.29 (13)C6A—C1—C9—C1124.69 (19)
C3—C3A—C6A—C6160.00 (10)C8—O1—C10—O3177.53 (12)
C4—C3A—C6A—C641.45 (12)C8—O1—C10—C94.47 (14)
C13—C3A—C6A—C1162.38 (11)C11—C9—C10—O369.47 (18)
C3—C3A—C6A—C137.67 (11)C1—C9—C10—O3165.31 (14)
C4—C3A—C6A—C180.88 (10)C11—C9—C10—O1108.30 (12)
O2—C5—C6—C6A170.68 (13)C1—C9—C10—O116.93 (13)
C4—C5—C6—C6A9.94 (13)
 

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