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Two subsets of data, corresponding to different crystalline modifications of the title compound, 5-oxatricyclo­[5.1.0.01,3]octane-4-one (C7H8O2), have been obtained from the same experiment. Both structures were successfully solved and refined. The packing of identical layers of molecules is different for monoclinic and orthorhombic forms.
Keywords: polymorphs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810200887X/an0591sup1.cif
Contains datablocks global, a, b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810200887X/an0591sup2.hkl
Contains datablocks a, b

CCDC references: 193577; 193578

Computing details top

For both compounds, data collection: Bruker SMART; cell refinement: Bruker SAINT; data reduction: Bruker SHELXTL; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
(a) 5-oxatricyclo[5.1.0.01,3]octane-4-one top
Crystal data top
C7H8O2Dx = 1.358 Mg m3
Mr = 124.13Melting point = 42–43 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 9.9644 (8) ÅCell parameters from 4038 reflections
b = 8.1854 (7) Åθ = 2.3–30.1°
c = 7.4422 (6) ŵ = 0.10 mm1
V = 607.01 (9) Å3T = 110 K
Z = 4Plate, colourless
F(000) = 2640.48 × 0.34 × 0.16 mm
Data collection top
Bruker SMART CCD 1K
diffractometer
1166 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 30.2°, θmin = 3.2°
Detector resolution: 8 pixels mm-1h = 1313
ω–scank = 1111
4859 measured reflectionsl = 1010
1266 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037All H-atom parameters refined
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max < 0.001
1266 reflectionsΔρmax = 0.16 e Å3
114 parametersΔρmin = 0.15 e Å3
0 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.2 (12)
Crystal data top
C7H8O2V = 607.01 (9) Å3
Mr = 124.13Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.9644 (8) ŵ = 0.10 mm1
b = 8.1854 (7) ÅT = 110 K
c = 7.4422 (6) Å0.48 × 0.34 × 0.16 mm
Data collection top
Bruker SMART CCD 1K
diffractometer
1166 reflections with I > 2σ(I)
4859 measured reflectionsRint = 0.049
1266 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037All H-atom parameters refined
wR(F2) = 0.089Δρmax = 0.16 e Å3
S = 1.17Δρmin = 0.15 e Å3
1266 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
114 parametersAbsolute structure parameter: 0.2 (12)
0 restraints
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
O10.21905 (11)0.15125 (12)0.26290 (18)0.0260 (3)
O20.38301 (9)0.02799 (12)0.25365 (16)0.0210 (2)
C10.34883 (14)0.32494 (17)0.2517 (2)0.0201 (3)
C20.26266 (16)0.42739 (19)0.1214 (2)0.0252 (3)
C30.15590 (15)0.12333 (19)0.1939 (2)0.0198 (3)
C40.09789 (14)0.2307 (2)0.3476 (2)0.0239 (3)
C50.20336 (14)0.29164 (17)0.2272 (2)0.0196 (3)
C60.43111 (15)0.18587 (19)0.1806 (2)0.0213 (3)
C70.25171 (13)0.01082 (17)0.23866 (19)0.0190 (3)
H1A0.382 (2)0.378 (2)0.365 (3)0.028 (5)*
H2A0.2750 (19)0.401 (3)0.013 (3)0.033 (6)*
H2B0.2432 (19)0.536 (3)0.165 (3)0.023 (5)*
H3A0.0930 (16)0.098 (2)0.090 (2)0.022 (5)*
H4A0.125 (2)0.205 (3)0.476 (3)0.041 (5)*
H4B0.0041 (14)0.262 (2)0.332 (3)0.019 (5)*
H6A0.5222 (16)0.196 (2)0.208 (2)0.012 (4)*
H6B0.4208 (15)0.175 (3)0.050 (2)0.019 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0261 (5)0.0182 (5)0.0339 (6)0.0019 (4)0.0004 (5)0.0015 (5)
O20.0166 (5)0.0185 (5)0.0279 (5)0.0011 (3)0.0010 (4)0.0019 (4)
C10.0197 (6)0.0174 (6)0.0230 (6)0.0009 (5)0.0016 (6)0.0008 (6)
C20.0317 (8)0.0172 (7)0.0269 (8)0.0031 (6)0.0025 (6)0.0046 (6)
C30.0189 (6)0.0192 (7)0.0213 (7)0.0003 (5)0.0024 (5)0.0011 (6)
C40.0177 (7)0.0269 (8)0.0272 (8)0.0044 (6)0.0032 (6)0.0011 (6)
C50.0194 (6)0.0190 (7)0.0203 (6)0.0016 (5)0.0014 (5)0.0007 (5)
C60.0190 (6)0.0197 (7)0.0252 (7)0.0027 (6)0.0030 (5)0.0001 (6)
C70.0199 (6)0.0202 (6)0.0169 (6)0.0014 (5)0.0013 (5)0.0003 (5)
Geometric parameters (Å, º) top
O1—C71.2082 (18)C3—C51.477 (2)
O2—C71.3510 (17)C3—C71.493 (2)
O2—C61.4816 (18)C3—C41.555 (2)
C1—C51.4861 (19)C3—H3A1.017 (18)
C1—C61.499 (2)C4—C51.469 (2)
C1—C21.543 (2)C4—H4A1.01 (2)
C1—H1A1.00 (2)C4—H4B0.976 (14)
C2—C51.484 (2)C6—H6A0.935 (16)
C2—H2A1.03 (2)C6—H6B0.982 (18)
C2—H2B0.97 (2)
C7—O2—C6119.22 (11)C5—C4—H4A116.9 (14)
C5—C1—C6110.55 (11)C3—C4—H4A118.2 (14)
C5—C1—C258.66 (9)C5—C4—H4B121.6 (12)
C6—C1—C2119.70 (13)C3—C4—H4B114.6 (11)
C5—C1—H1A120.0 (11)H4A—C4—H4B115.2 (16)
C6—C1—H1A116.6 (11)C4—C5—C363.70 (10)
C2—C1—H1A118.3 (11)C4—C5—C2149.61 (14)
C5—C2—C158.76 (9)C3—C5—C2137.43 (15)
C5—C2—H2A114.0 (12)C4—C5—C1133.27 (14)
C1—C2—H2A115.5 (11)C3—C5—C1120.25 (12)
C5—C2—H2B115.7 (12)C2—C5—C162.58 (10)
C1—C2—H2B113.8 (13)O2—C6—C1110.85 (11)
H2A—C2—H2B122.6 (16)O2—C6—H6A107.9 (10)
C5—C3—C7116.34 (12)C1—C6—H6A112.8 (10)
C5—C3—C457.87 (10)O2—C6—H6B104.4 (12)
C7—C3—C4119.31 (13)C1—C6—H6B111.2 (11)
C5—C3—H3A120.9 (11)H6A—C6—H6B109.3 (13)
C7—C3—H3A114.5 (11)O1—C7—O2118.18 (12)
C4—C3—H3A116.4 (10)O1—C7—C3124.12 (13)
C5—C4—C358.43 (10)O2—C7—C3117.70 (12)
(b) 5-oxatricyclo[5.1.0.01,3]octane-4-one top
Crystal data top
C7H8O2Dx = 1.367 Mg m3
Mr = 124.13Melting point = 42–43 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.9533 (8) ÅCell parameters from 3630 reflections
b = 8.1831 (7) Åθ = 2.6–30.1°
c = 7.8129 (6) ŵ = 0.10 mm1
β = 108.61 (2)°T = 110 K
V = 603.06 (8) Å3Plate, colourless
Z = 40.48 × 0.34 × 0.16 mm
F(000) = 264
Data collection top
Bruker SMART CCD 1K
diffractometer
1061 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.043
Graphite monochromatorθmax = 30.2°, θmin = 2.2°
Detector resolution: 8 pixels mm-1h = 1313
ω–scank = 1111
4733 measured reflectionsl = 1010
1264 independent reflections
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126All H-atom parameters refined
S = 1.60 w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
1264 reflections(Δ/σ)max < 0.001
114 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C7H8O2V = 603.06 (8) Å3
Mr = 124.13Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.9533 (8) ŵ = 0.10 mm1
b = 8.1831 (7) ÅT = 110 K
c = 7.8129 (6) Å0.48 × 0.34 × 0.16 mm
β = 108.61 (2)°
Data collection top
Bruker SMART CCD 1K
diffractometer
1061 reflections with I > 2σ(I)
4733 measured reflectionsRint = 0.043
1264 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.126All H-atom parameters refined
S = 1.60Δρmax = 0.33 e Å3
1264 reflectionsΔρmin = 0.18 e Å3
114 parameters
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
O10.75403 (11)0.60977 (13)0.21444 (15)0.0261 (3)
O20.59845 (11)0.80545 (12)0.19477 (15)0.0243 (3)
C10.65810 (15)1.09741 (19)0.2253 (2)0.0220 (3)
C20.77115 (18)1.1846 (2)0.3804 (2)0.0265 (4)
C30.84934 (15)0.87395 (18)0.31893 (19)0.0195 (3)
C40.90300 (17)0.9773 (2)0.1871 (2)0.0235 (3)
C50.80878 (15)1.04741 (18)0.28113 (19)0.0187 (3)
C60.56940 (16)0.9651 (2)0.2670 (2)0.0245 (3)
C70.73306 (15)0.75293 (17)0.24005 (18)0.0191 (3)
H1A0.616 (2)1.159 (3)0.116 (3)0.037 (5)*
H2A0.788 (2)1.297 (2)0.350 (3)0.030 (5)*
H2B0.770 (2)1.158 (2)0.506 (3)0.030 (5)*
H3A0.931 (2)0.835 (3)0.434 (3)0.031 (5)*
H4A0.995 (3)0.999 (3)0.221 (3)0.036 (6)*
H4B0.868 (2)0.956 (2)0.064 (3)0.030 (5)*
H6A0.4684 (19)0.977 (2)0.205 (2)0.018 (4)*
H6B0.5890 (17)0.948 (2)0.391 (2)0.013 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0237 (6)0.0183 (5)0.0353 (6)0.0004 (4)0.0081 (5)0.0027 (4)
O20.0163 (5)0.0204 (6)0.0350 (6)0.0003 (4)0.0066 (4)0.0020 (4)
C10.0194 (7)0.0214 (7)0.0243 (7)0.0025 (5)0.0057 (6)0.0001 (5)
C20.0269 (8)0.0226 (8)0.0296 (8)0.0003 (6)0.0085 (6)0.0063 (6)
C30.0166 (6)0.0192 (7)0.0213 (7)0.0002 (5)0.0040 (5)0.0010 (5)
C40.0196 (8)0.0232 (7)0.0298 (8)0.0032 (5)0.0107 (6)0.0019 (6)
C50.0164 (7)0.0178 (7)0.0210 (6)0.0017 (5)0.0048 (5)0.0014 (5)
C60.0183 (7)0.0219 (8)0.0349 (8)0.0028 (5)0.0105 (6)0.0017 (6)
C70.0162 (7)0.0203 (7)0.0203 (6)0.0005 (5)0.0051 (5)0.0008 (5)
Geometric parameters (Å, º) top
O1—C71.2177 (18)C3—C51.479 (2)
O2—C71.3425 (17)C3—C71.4981 (19)
O2—C61.4874 (18)C3—C41.553 (2)
C1—C51.480 (2)C3—H3A1.05 (2)
C1—C61.497 (2)C4—C51.479 (2)
C1—C21.540 (2)C4—H4A0.89 (2)
C1—H1A0.97 (2)C4—H4B0.93 (2)
C2—C51.479 (2)C6—H6A0.971 (18)
C2—H2A0.98 (2)C6—H6B0.936 (17)
C2—H2B1.01 (2)
C7—O2—C6118.66 (11)C5—C4—H4A122.2 (14)
C5—C1—C6110.40 (12)C3—C4—H4A116.8 (14)
C5—C1—C258.61 (10)C5—C4—H4B119.8 (12)
C6—C1—C2119.84 (14)C3—C4—H4B119.0 (12)
C5—C1—H1A121.3 (12)H4A—C4—H4B111.2 (18)
C6—C1—H1A116.8 (13)C4—C5—C2149.48 (14)
C2—C1—H1A117.1 (13)C4—C5—C363.34 (10)
C5—C2—C158.65 (10)C2—C5—C3136.24 (13)
C5—C2—H2A119.7 (12)C4—C5—C1134.80 (13)
C1—C2—H2A112.5 (12)C2—C5—C162.74 (10)
C5—C2—H2B115.6 (11)C3—C5—C1120.69 (12)
C1—C2—H2B115.6 (12)O2—C6—C1110.68 (12)
H2A—C2—H2B119.6 (16)O2—C6—H6A101.2 (11)
C5—C3—C7115.23 (12)C1—C6—H6A114.1 (11)
C5—C3—C458.31 (9)O2—C6—H6B105.1 (10)
C7—C3—C4118.12 (12)C1—C6—H6B113.0 (10)
C5—C3—H3A123.3 (11)H6A—C6—H6B111.8 (14)
C7—C3—H3A115.9 (11)O1—C7—O2118.27 (13)
C4—C3—H3A113.4 (11)O1—C7—C3123.58 (13)
C5—C4—C358.35 (9)O2—C7—C3118.15 (12)
C6—C1—C2—C596.93 (15)C6—C1—C5—C2113.27 (15)
C7—C3—C4—C5103.78 (14)C6—C1—C5—C316.45 (19)
C3—C4—C5—C2137.7 (3)C2—C1—C5—C3129.72 (16)
C3—C4—C5—C1107.84 (19)C7—O2—C6—C153.47 (18)
C1—C2—C5—C4133.4 (3)C5—C1—C6—O250.68 (17)
C1—C2—C5—C3106.99 (19)C2—C1—C6—O2115.38 (15)
C7—C3—C5—C4108.74 (14)C6—O2—C7—O1164.39 (13)
C7—C3—C5—C2100.9 (2)C6—O2—C7—C315.77 (19)
C4—C3—C5—C2150.4 (2)C5—C3—C7—O1159.22 (14)
C7—C3—C5—C119.50 (19)C4—C3—C7—O193.22 (17)
C4—C3—C5—C1128.24 (16)C5—C3—C7—O220.60 (18)
C6—C1—C5—C498.1 (2)C4—C3—C7—O286.61 (16)
C2—C1—C5—C4148.7 (2)

Experimental details

(a)(b)
Crystal data
Chemical formulaC7H8O2C7H8O2
Mr124.13124.13
Crystal system, space groupOrthorhombic, P212121Monoclinic, P21/c
Temperature (K)110110
a, b, c (Å)9.9644 (8), 8.1854 (7), 7.4422 (6)9.9533 (8), 8.1831 (7), 7.8129 (6)
α, β, γ (°)90, 90, 9090, 108.61 (2), 90
V3)607.01 (9)603.06 (8)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.100.10
Crystal size (mm)0.48 × 0.34 × 0.160.48 × 0.34 × 0.16
Data collection
DiffractometerBruker SMART CCD 1K
diffractometer
Bruker SMART CCD 1K
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4859, 1266, 1166 4733, 1264, 1061
Rint0.0490.043
(sin θ/λ)max1)0.7090.707
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.089, 1.17 0.047, 0.126, 1.60
No. of reflections12661264
No. of parameters114114
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.16, 0.150.33, 0.18
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881?
Absolute structure parameter0.2 (12)?

Computer programs: Bruker SMART, Bruker SAINT, Bruker SHELXTL, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).

Selected geometric parameters (Å, º) for (a) top
O1—C71.2082 (18)C2—C51.484 (2)
O2—C71.3510 (17)C3—C51.477 (2)
O2—C61.4816 (18)C3—C71.493 (2)
C1—C51.4861 (19)C3—C41.555 (2)
C1—C61.499 (2)C4—C51.469 (2)
C1—C21.543 (2)
C7—O2—C6119.22 (11)C4—C5—C2149.61 (14)
C5—C1—C6110.55 (11)C3—C5—C2137.43 (15)
C5—C1—C258.66 (9)C4—C5—C1133.27 (14)
C6—C1—C2119.70 (13)C3—C5—C1120.25 (12)
C5—C2—C158.76 (9)C2—C5—C162.58 (10)
C5—C3—C7116.34 (12)O2—C6—C1110.85 (11)
C5—C3—C457.87 (10)O1—C7—O2118.18 (12)
C7—C3—C4119.31 (13)O1—C7—C3124.12 (13)
C5—C4—C358.43 (10)O2—C7—C3117.70 (12)
C4—C5—C363.70 (10)
Selected geometric parameters (Å, º) for (b) top
O1—C71.2177 (18)C2—C51.479 (2)
O2—C71.3425 (17)C3—C51.479 (2)
O2—C61.4874 (18)C3—C71.4981 (19)
C1—C51.480 (2)C3—C41.553 (2)
C1—C61.497 (2)C4—C51.479 (2)
C1—C21.540 (2)
C7—O2—C6118.66 (11)C4—C5—C363.34 (10)
C5—C1—C6110.40 (12)C2—C5—C3136.24 (13)
C5—C1—C258.61 (10)C4—C5—C1134.80 (13)
C6—C1—C2119.84 (14)C2—C5—C162.74 (10)
C5—C2—C158.65 (10)C3—C5—C1120.69 (12)
C5—C3—C7115.23 (12)O2—C6—C1110.68 (12)
C5—C3—C458.31 (9)O1—C7—O2118.27 (13)
C7—C3—C4118.12 (12)O1—C7—C3123.58 (13)
C5—C4—C358.35 (9)O2—C7—C3118.15 (12)
C4—C5—C2149.48 (14)
 

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