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The anti stereochemistry between the fused rings of the bicyclic lactone (\pm)-2,5-dioxoper­hydro­cyclo­octa­[b]­furan-3-carboxyl­ic acid, C11H14O5, has been established. Intermolec­ular hydrogen bonds are observed between the carboxyl­ic acid group and the carbonyl O atom of an adjacent mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001964/ww6006sup1.cif
Contains datablocks k59_01, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001964/ww6006Isup2.hkl
Contains datablock I

CCDC reference: 182606

Key indicators

  • Single-crystal X-ray study
  • T = 123 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.095
  • Data-to-parameter ratio = 18.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

The anti stereochemistry of the fused ring systems of the title compound, (I), has been established. The molecular structure of (I) is shown in Fig. 1. A hydrogen-bonded chain structure is formed through an intermolecular hydrogen bond between the carboxylic acid group and the ketone O atom of an adjacent molecule.

Experimental top

The title compound was prepared by base-catalyzed hydrolysis of the parent ethyl ester (26a) as previously described (Greatrex et al., 2002). Crystals suitable for X-ray analysis were grown by slow evaporation from an ethyl acetate/hexane (1:1) solution of the compound.

Refinement top

The H atoms were included in the riding-model approximation. The torsion angle about the C—O bond of the carboxylic acid group has been refined.

Computing details top

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of (I) (50% probability displacement ellipsoids).
(I) top
Crystal data top
C11H14O5Dx = 1.416 Mg m3
Mr = 226.22Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 25701 reflections
a = 8.0792 (1) Åθ = 3–28.3°
b = 10.6879 (2) ŵ = 0.11 mm1
c = 24.5704 (5) ÅT = 123 K
V = 2121.65 (6) Å3Tabular, colourless
Z = 80.24 × 0.14 × 0.04 mm
F(000) = 960
Data collection top
KappaCCD
diffractometer
θmax = 28.3°, θmin = 3.0°
CCD rotation images, thick slices scansh = 1010
23956 measured reflectionsk = 1414
2630 independent reflectionsl = 3232
1847 reflections with I > 2σ(I)
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.043 w = 1/[σ2(Fo2) + (0.0434P)2 + 0.2022P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.095(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.21 e Å3
2630 reflectionsΔρmin = 0.22 e Å3
146 parameters
Crystal data top
C11H14O5V = 2121.65 (6) Å3
Mr = 226.22Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 8.0792 (1) ŵ = 0.11 mm1
b = 10.6879 (2) ÅT = 123 K
c = 24.5704 (5) Å0.24 × 0.14 × 0.04 mm
Data collection top
KappaCCD
diffractometer
2630 independent reflections
23956 measured reflections1847 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.21 e Å3
2630 reflectionsΔρmin = 0.22 e Å3
146 parameters
Special details top

Experimental. m.p. 128–102°C decomp.

IR(nujol) 1776, 1726, 1677, 1377, 1162 cm-1.

1H n.m.r. (600 MHz, CDCl3): δ 1.42–1.48 (m, 1H), 1.73–1.86 (m,3H), 1.88–1.94 (m, 1H), 2.19–2.24 (m, 1H), 2.33–2.37 (m, 1H), 2.42–2.47 (dd,J=12, 14.4 Hz, 1H), 2.73–2.78 (m,1H), 3.01–3.04 (dd,J=3.6, 14.4 Hz, 1H), 3.10–3.16 (m,1H), 3.39 (d,J=12.6 Hz, 1H), 4.18–4.21 (m, 1H).

MS (M+,%) 226 (M.+, 10), 208 (27), 153 (22), 125 (23), 124 (88), 95 (40), 68 (55), 41 (100).

HRMS Calcd. for C11H14O5: 226.0841; Found: 226.0849.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C20.25936 (17)0.71910 (12)0.39367 (5)0.0222 (3)
C30.18115 (16)0.76712 (12)0.34165 (5)0.0195 (3)
H20.24450.84180.32870.023*
C3A0.00819 (16)0.80962 (12)0.36046 (5)0.0187 (3)
H30.06810.7360.36040.022*
C40.06406 (16)0.91178 (12)0.32415 (5)0.0201 (3)
H10A0.01540.98230.32320.024*
H10B0.07240.87830.28670.024*
C50.23037 (17)0.96266 (12)0.33993 (5)0.0199 (3)
C60.35421 (17)0.88299 (13)0.36949 (6)0.0238 (3)
H8A0.31560.79510.36980.029*
H8B0.46150.88590.35010.029*
C70.37844 (18)0.92861 (13)0.42852 (6)0.0263 (3)
H7A0.44211.00780.42780.032*
H7B0.44550.8660.44840.032*
C80.21789 (18)0.95045 (13)0.45991 (5)0.0264 (3)
H6A0.24650.97240.49790.032*
H6B0.16081.02360.44380.032*
C90.09544 (17)0.83986 (13)0.46108 (5)0.0244 (3)
H5A0.04580.83470.49780.029*
H5B0.15770.76140.45470.029*
C9A0.04278 (16)0.84862 (12)0.41947 (5)0.0212 (3)
H40.08770.93580.41960.025*
C100.17803 (15)0.67021 (13)0.29689 (5)0.0206 (3)
O10.17430 (11)0.76198 (9)0.43694 (4)0.0264 (3)
O20.38100 (12)0.65480 (9)0.39857 (4)0.0287 (3)
O30.26599 (13)1.07091 (9)0.32865 (4)0.0284 (3)
O40.18102 (12)0.55878 (9)0.30398 (4)0.0288 (3)
O50.16712 (14)0.72439 (9)0.24839 (4)0.0329 (3)
H50.17950.67030.2240.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0224 (7)0.0189 (7)0.0252 (7)0.0024 (6)0.0015 (6)0.0006 (6)
C30.0194 (7)0.0179 (6)0.0213 (7)0.0005 (5)0.0002 (5)0.0013 (6)
C3A0.0182 (7)0.0176 (6)0.0203 (7)0.0010 (5)0.0005 (6)0.0003 (6)
C40.0212 (7)0.0210 (7)0.0182 (7)0.0003 (5)0.0000 (6)0.0016 (5)
C50.0230 (7)0.0214 (7)0.0152 (6)0.0015 (6)0.0025 (6)0.0017 (5)
C60.0194 (7)0.0247 (7)0.0272 (8)0.0002 (6)0.0007 (6)0.0003 (6)
C70.0248 (8)0.0273 (8)0.0268 (8)0.0008 (6)0.0066 (6)0.0019 (6)
C80.0328 (9)0.0254 (8)0.0210 (7)0.0004 (6)0.0055 (6)0.0020 (6)
C90.0300 (8)0.0253 (8)0.0181 (7)0.0011 (6)0.0002 (6)0.0011 (6)
C9A0.0229 (7)0.0193 (7)0.0214 (7)0.0016 (6)0.0029 (6)0.0004 (6)
C100.0154 (7)0.0218 (7)0.0247 (8)0.0016 (6)0.0025 (6)0.0010 (6)
O10.0275 (5)0.0295 (6)0.0222 (5)0.0065 (4)0.0028 (4)0.0017 (4)
O20.0268 (5)0.0268 (6)0.0325 (6)0.0061 (5)0.0060 (5)0.0024 (4)
O30.0336 (6)0.0229 (5)0.0287 (6)0.0078 (4)0.0074 (5)0.0057 (4)
O40.0352 (6)0.0182 (5)0.0331 (6)0.0002 (4)0.0007 (5)0.0003 (4)
O50.0554 (7)0.0230 (5)0.0205 (5)0.0036 (5)0.0037 (5)0.0017 (4)
Geometric parameters (Å, º) top
C2—O21.2052 (16)C6—H8B0.99
C2—O11.3464 (16)C7—C81.527 (2)
C2—C31.5152 (18)C7—H7A0.99
C3—C101.5110 (18)C7—H7B0.99
C3—C3A1.5403 (18)C8—C91.5416 (19)
C3—H21C8—H6A0.99
C3A—C41.5261 (18)C8—H6B0.99
C3A—C9A1.5342 (18)C9—C9A1.5169 (18)
C3A—H31C9—H5A0.99
C4—C51.5005 (19)C9—H5B0.99
C4—H10A0.99C9A—O11.4734 (15)
C4—H10B0.99C9A—H41
C5—O31.2240 (15)C10—O41.2040 (15)
C5—C61.5013 (19)C10—O51.3277 (17)
C6—C71.5426 (19)O5—H50.84
C6—H8A0.99
O2—C2—O1122.10 (12)C8—C7—C6114.54 (11)
O2—C2—C3128.13 (12)C8—C7—H7A108.6
O1—C2—C3109.75 (11)C6—C7—H7A108.6
C10—C3—C2112.87 (11)C8—C7—H7B108.6
C10—C3—C3A113.92 (10)C6—C7—H7B108.6
C2—C3—C3A103.02 (10)H7A—C7—H7B107.6
C10—C3—H2108.9C7—C8—C9115.93 (12)
C2—C3—H2108.9C7—C8—H6A108.3
C3A—C3—H2108.9C9—C8—H6A108.3
C4—C3A—C9A115.33 (11)C7—C8—H6B108.3
C4—C3A—C3112.50 (11)C9—C8—H6B108.3
C9A—C3A—C3101.44 (10)H6A—C8—H6B107.4
C4—C3A—H3109.1C9A—C9—C8114.36 (11)
C9A—C3A—H3109.1C9A—C9—H5A108.7
C3—C3A—H3109.1C8—C9—H5A108.7
C5—C4—C3A116.79 (11)C9A—C9—H5B108.7
C5—C4—H10A108.1C8—C9—H5B108.7
C3A—C4—H10A108.1H5A—C9—H5B107.6
C5—C4—H10B108.1O1—C9A—C9107.20 (10)
C3A—C4—H10B108.1O1—C9A—C3A103.65 (10)
H10A—C4—H10B107.3C9—C9A—C3A119.08 (11)
O3—C5—C4119.65 (12)O1—C9A—H4108.8
O3—C5—C6119.27 (12)C9—C9A—H4108.8
C4—C5—C6121.08 (11)C3A—C9A—H4108.8
C5—C6—C7111.11 (11)O4—C10—O5124.24 (13)
C5—C6—H8A109.4O4—C10—C3124.92 (12)
C7—C6—H8A109.4O5—C10—C3110.82 (11)
C5—C6—H8B109.4C2—O1—C9A110.61 (10)
C7—C6—H8B109.4C10—O5—H5109.5
H8A—C6—H8B108
O2—C2—C3—C1041.29 (19)C7—C8—C9—C9A98.00 (15)
O1—C2—C3—C10140.41 (11)C8—C9—C9A—O1162.10 (11)
O2—C2—C3—C3A164.60 (13)C8—C9—C9A—C3A80.84 (15)
O1—C2—C3—C3A17.11 (14)C4—C3A—C9A—O1154.82 (10)
C10—C3—C3A—C483.43 (13)C3—C3A—C9A—O132.98 (12)
C2—C3—C3A—C4153.96 (11)C4—C3A—C9A—C986.28 (14)
C10—C3—C3A—C9A152.78 (11)C3—C3A—C9A—C9151.87 (11)
C2—C3—C3A—C9A30.16 (12)C2—C3—C10—O424.40 (19)
C9A—C3A—C4—C562.51 (16)C3A—C3—C10—O492.64 (16)
C3—C3A—C4—C5178.20 (11)C2—C3—C10—O5157.24 (11)
C3A—C4—C5—O3150.56 (12)C3A—C3—C10—O585.72 (13)
C3A—C4—C5—C629.34 (18)O2—C2—O1—C9A173.95 (12)
O3—C5—C6—C768.98 (16)C3—C2—O1—C9A4.47 (14)
C4—C5—C6—C7110.92 (13)C9—C9A—O1—C2151.11 (11)
C5—C6—C7—C848.88 (16)C3A—C9A—O1—C224.33 (13)
C6—C7—C8—C953.38 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O3i0.841.812.6292 (13)164
Symmetry code: (i) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC11H14O5
Mr226.22
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)123
a, b, c (Å)8.0792 (1), 10.6879 (2), 24.5704 (5)
V3)2121.65 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.24 × 0.14 × 0.04
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
23956, 2630, 1847
Rint?
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.095, 1.06
No. of reflections2630
No. of parameters146
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.22

Computer programs: COLLECT (Nonius, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O3i0.841.812.6292 (13)163.6
Symmetry code: (i) x, y1/2, z+1/2.
 

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