Acta Cryst. (2013). E69, o204 [ doi:10.1107/S1600536813000147 ]
The title compound, C24H40O2, lies on an inversion center with a half-molecule in the asymmetric unit. The central dioxane ring adopts a chair conformation. The four-membered ring is slightly puckered with a butterfly angle of 13.50 (14)°.
The synthesis of the title compound has been reported earlier (Rauk et al., 1995). Crystals suitable for crystallolgraphic studies were grown from pentane/CH2Cl2 (1:1).
Though the H-atoms were observable in the difference electron density maps they were included at geometrically idealized positions with C—H distances = 0.99 and 0.98 Å for methylene and methyl type H-atoms, respectively. The H-atoms were assigned Uiso = 1.2 times Ueq(C).
Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./zl2528fig1thm.gif)
| Fig. 1. ORTEP drawing (Farrugia, 2012) of the title molecule with the displacement ellipsoids plotted at 50% probability level; H atoms are presented as small spheres of arbitrary radius. Symmetry code: i -x + 1, -y + 1, -z + 1. |
![[Figure 2]](./zl2528fig2thm.gif)
| Fig. 2. A view of the unit cell packing of the crystal structure of the title compound. H atoms were omitted for clarity. |
| C24H40O2 | Z = 1 |
| Mr = 360.56 | F(000) = 200 |
| Triclinic, P1 | Dx = 1.116 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 5.843 (2) Å | Cell parameters from 2272 reflections |
| b = 9.383 (3) Å | θ = 1.0–27.5° |
| c = 10.126 (4) Å | µ = 0.07 mm−1 |
| α = 97.209 (12)° | T = 170 K |
| β = 96.014 (13)° | Plate, colorless |
| γ = 100.703 (19)° | 0.20 × 0.15 × 0.05 mm |
| V = 536.5 (3) Å3 |
| Nonius APEXII CCD diffractometer | 2412 independent reflections |
| Radiation source: fine-focus sealed tube | 1957 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.018 |
| ω and φ scans | θmax = 27.4°, θmin = 4.1° |
| Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −7→7 |
| Tmin = 0.987, Tmax = 0.997 | k = −12→12 |
| 4499 measured reflections | l = −13→13 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.104 | H-atom parameters constrained |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0415P)2 + 0.1563P] where P = (Fo2 + 2Fc2)/3 |
| 2412 reflections | (Δ/σ)max < 0.001 |
| 124 parameters | Δρmax = 0.27 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
| C24H40O2 | γ = 100.703 (19)° |
| Mr = 360.56 | V = 536.5 (3) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 5.843 (2) Å | Mo Kα radiation |
| b = 9.383 (3) Å | µ = 0.07 mm−1 |
| c = 10.126 (4) Å | T = 170 K |
| α = 97.209 (12)° | 0.20 × 0.15 × 0.05 mm |
| β = 96.014 (13)° |
| Nonius APEXII CCD diffractometer | 2412 independent reflections |
| Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 1957 reflections with I > 2σ(I) |
| Tmin = 0.987, Tmax = 0.997 | Rint = 0.018 |
| 4499 measured reflections | θmax = 27.4° |
| R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
| wR(F2) = 0.104 | Δρmax = 0.27 e Å−3 |
| S = 1.04 | Δρmin = −0.19 e Å−3 |
| 2412 reflections | Absolute structure: ? |
| 124 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.25855 (13) | 0.40276 (8) | 0.50016 (8) | 0.0194 (2) | |
| C1 | 0.36790 (19) | 0.43605 (12) | 0.39096 (11) | 0.0183 (2) | |
| C2 | 0.38127 (19) | 0.36693 (12) | 0.26899 (11) | 0.0195 (2) | |
| C3 | 0.6042 (2) | 0.47693 (13) | 0.25541 (12) | 0.0225 (3) | |
| H3A | 0.5931 | 0.5253 | 0.1742 | 0.027* | |
| H3B | 0.7506 | 0.4384 | 0.2666 | 0.027* | |
| C4 | 0.44599 (19) | 0.43136 (12) | 0.61504 (11) | 0.0184 (2) | |
| C5 | 0.2453 (2) | 0.23533 (13) | 0.17350 (12) | 0.0226 (3) | |
| C6 | 0.0667 (2) | 0.14183 (14) | 0.24394 (13) | 0.0304 (3) | |
| H6A | −0.0295 | 0.0617 | 0.1785 | 0.037* | |
| H6B | −0.0346 | 0.2029 | 0.2839 | 0.037* | |
| H6C | 0.1499 | 0.1010 | 0.3146 | 0.037* | |
| C7 | 0.4145 (2) | 0.14319 (15) | 0.11795 (14) | 0.0343 (3) | |
| H7A | 0.3251 | 0.0586 | 0.0549 | 0.041* | |
| H7B | 0.5003 | 0.1089 | 0.1921 | 0.041* | |
| H7C | 0.5263 | 0.2032 | 0.0714 | 0.041* | |
| C8 | 0.1150 (2) | 0.28994 (15) | 0.05637 (13) | 0.0335 (3) | |
| H8A | 0.0317 | 0.2058 | −0.0093 | 0.040* | |
| H8B | 0.2283 | 0.3532 | 0.0133 | 0.040* | |
| H8C | 0.0017 | 0.3457 | 0.0903 | 0.040* | |
| C9 | 0.5229 (2) | 0.28551 (12) | 0.63873 (12) | 0.0219 (3) | |
| C10 | 0.7097 (2) | 0.30967 (15) | 0.76230 (14) | 0.0325 (3) | |
| H10A | 0.7518 | 0.2159 | 0.7764 | 0.039* | |
| H10B | 0.6468 | 0.3501 | 0.8416 | 0.039* | |
| H10C | 0.8497 | 0.3785 | 0.7477 | 0.039* | |
| C11 | 0.3063 (2) | 0.17552 (14) | 0.66121 (14) | 0.0306 (3) | |
| H11A | 0.3515 | 0.0826 | 0.6755 | 0.037* | |
| H11B | 0.1872 | 0.1588 | 0.5822 | 0.037* | |
| H11C | 0.2418 | 0.2149 | 0.7403 | 0.037* | |
| C12 | 0.6320 (2) | 0.22114 (13) | 0.51932 (13) | 0.0273 (3) | |
| H12A | 0.6876 | 0.1332 | 0.5403 | 0.033* | |
| H12B | 0.7646 | 0.2940 | 0.5018 | 0.033* | |
| H12C | 0.5136 | 0.1952 | 0.4396 | 0.033* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0169 (4) | 0.0215 (4) | 0.0192 (4) | 0.0009 (3) | 0.0034 (3) | 0.0036 (3) |
| C1 | 0.0168 (5) | 0.0176 (5) | 0.0209 (6) | 0.0029 (4) | 0.0030 (4) | 0.0050 (4) |
| C2 | 0.0194 (5) | 0.0186 (5) | 0.0202 (6) | 0.0028 (4) | 0.0029 (4) | 0.0033 (4) |
| C3 | 0.0249 (6) | 0.0216 (6) | 0.0204 (6) | 0.0019 (5) | 0.0060 (5) | 0.0022 (5) |
| C4 | 0.0179 (5) | 0.0192 (5) | 0.0173 (6) | 0.0016 (4) | 0.0023 (4) | 0.0026 (4) |
| C5 | 0.0223 (6) | 0.0224 (6) | 0.0212 (6) | 0.0024 (5) | 0.0022 (5) | −0.0007 (5) |
| C6 | 0.0286 (6) | 0.0280 (7) | 0.0292 (7) | −0.0041 (5) | 0.0021 (5) | −0.0005 (5) |
| C7 | 0.0310 (7) | 0.0306 (7) | 0.0373 (8) | 0.0061 (6) | 0.0040 (6) | −0.0098 (6) |
| C8 | 0.0367 (7) | 0.0359 (7) | 0.0244 (7) | 0.0045 (6) | −0.0033 (5) | 0.0010 (5) |
| C9 | 0.0241 (6) | 0.0188 (6) | 0.0230 (6) | 0.0028 (4) | 0.0034 (5) | 0.0059 (5) |
| C10 | 0.0387 (7) | 0.0283 (7) | 0.0307 (7) | 0.0095 (6) | −0.0036 (6) | 0.0081 (5) |
| C11 | 0.0340 (7) | 0.0208 (6) | 0.0382 (7) | 0.0020 (5) | 0.0091 (6) | 0.0098 (5) |
| C12 | 0.0305 (6) | 0.0226 (6) | 0.0312 (7) | 0.0106 (5) | 0.0054 (5) | 0.0046 (5) |
| O1—C1 | 1.3744 (14) | C7—H7A | 0.9800 |
| O1—C4 | 1.4733 (14) | C7—H7B | 0.9800 |
| C1—C2 | 1.3380 (16) | C7—H7C | 0.9800 |
| C1—C4i | 1.5048 (15) | C8—H8A | 0.9800 |
| C2—C5 | 1.5053 (16) | C8—H8B | 0.9800 |
| C2—C3 | 1.5344 (16) | C8—H8C | 0.9800 |
| C3—C4i | 1.5615 (16) | C9—C11 | 1.5338 (17) |
| C3—H3A | 0.9900 | C9—C12 | 1.5347 (17) |
| C3—H3B | 0.9900 | C9—C10 | 1.5361 (18) |
| C4—C1i | 1.5048 (15) | C10—H10A | 0.9800 |
| C4—C9 | 1.5557 (16) | C10—H10B | 0.9800 |
| C4—C3i | 1.5615 (16) | C10—H10C | 0.9800 |
| C5—C6 | 1.5299 (17) | C11—H11A | 0.9800 |
| C5—C7 | 1.5340 (17) | C11—H11B | 0.9800 |
| C5—C8 | 1.5354 (18) | C11—H11C | 0.9800 |
| C6—H6A | 0.9800 | C12—H12A | 0.9800 |
| C6—H6B | 0.9800 | C12—H12B | 0.9800 |
| C6—H6C | 0.9800 | C12—H12C | 0.9800 |
| C1—O1—C4 | 105.98 (8) | C5—C7—H7C | 109.5 |
| C2—C1—O1 | 136.58 (10) | H7A—C7—H7C | 109.5 |
| C2—C1—C4i | 95.84 (9) | H7B—C7—H7C | 109.5 |
| O1—C1—C4i | 127.01 (10) | C5—C8—H8A | 109.5 |
| C1—C2—C5 | 137.73 (11) | C5—C8—H8B | 109.5 |
| C1—C2—C3 | 91.75 (9) | H8A—C8—H8B | 109.5 |
| C5—C2—C3 | 130.52 (10) | C5—C8—H8C | 109.5 |
| C2—C3—C4i | 86.07 (8) | H8A—C8—H8C | 109.5 |
| C2—C3—H3A | 114.3 | H8B—C8—H8C | 109.5 |
| C4i—C3—H3A | 114.3 | C11—C9—C12 | 109.70 (10) |
| C2—C3—H3B | 114.3 | C11—C9—C10 | 109.15 (10) |
| C4i—C3—H3B | 114.3 | C12—C9—C10 | 106.61 (10) |
| H3A—C3—H3B | 111.5 | C11—C9—C4 | 108.43 (10) |
| O1—C4—C1i | 112.31 (9) | C12—C9—C4 | 111.81 (10) |
| O1—C4—C9 | 109.61 (9) | C10—C9—C4 | 111.11 (10) |
| C1i—C4—C9 | 118.82 (9) | C9—C10—H10A | 109.5 |
| O1—C4—C3i | 115.51 (9) | C9—C10—H10B | 109.5 |
| C1i—C4—C3i | 84.71 (8) | H10A—C10—H10B | 109.5 |
| C9—C4—C3i | 114.21 (9) | C9—C10—H10C | 109.5 |
| C2—C5—C6 | 110.63 (10) | H10A—C10—H10C | 109.5 |
| C2—C5—C7 | 109.91 (10) | H10B—C10—H10C | 109.5 |
| C6—C5—C7 | 109.95 (11) | C9—C11—H11A | 109.5 |
| C2—C5—C8 | 108.22 (10) | C9—C11—H11B | 109.5 |
| C6—C5—C8 | 109.26 (11) | H11A—C11—H11B | 109.5 |
| C7—C5—C8 | 108.82 (11) | C9—C11—H11C | 109.5 |
| C5—C6—H6A | 109.5 | H11A—C11—H11C | 109.5 |
| C5—C6—H6B | 109.5 | H11B—C11—H11C | 109.5 |
| H6A—C6—H6B | 109.5 | C9—C12—H12A | 109.5 |
| C5—C6—H6C | 109.5 | C9—C12—H12B | 109.5 |
| H6A—C6—H6C | 109.5 | H12A—C12—H12B | 109.5 |
| H6B—C6—H6C | 109.5 | C9—C12—H12C | 109.5 |
| C5—C7—H7A | 109.5 | H12A—C12—H12C | 109.5 |
| C5—C7—H7B | 109.5 | H12B—C12—H12C | 109.5 |
| H7A—C7—H7B | 109.5 | ||
| C4—O1—C1—C2 | 124.33 (14) | C1—C2—C5—C7 | −133.88 (15) |
| C4—O1—C1—C4i | −44.73 (14) | C3—C2—C5—C7 | 46.30 (16) |
| O1—C1—C2—C5 | 19.1 (2) | C1—C2—C5—C8 | 107.40 (16) |
| C4i—C1—C2—C5 | −169.70 (13) | C3—C2—C5—C8 | −72.42 (15) |
| O1—C1—C2—C3 | −161.07 (13) | O1—C4—C9—C11 | −57.21 (12) |
| C4i—C1—C2—C3 | 10.17 (9) | C1i—C4—C9—C11 | 171.79 (10) |
| C1—C2—C3—C4i | −9.77 (9) | C3i—C4—C9—C11 | 74.21 (12) |
| C5—C2—C3—C4i | 170.11 (12) | O1—C4—C9—C12 | 63.86 (12) |
| C1—O1—C4—C1i | 37.41 (12) | C1i—C4—C9—C12 | −67.14 (13) |
| C1—O1—C4—C9 | −96.97 (10) | C3i—C4—C9—C12 | −164.73 (9) |
| C1—O1—C4—C3i | 132.31 (10) | O1—C4—C9—C10 | −177.16 (9) |
| C1—C2—C5—C6 | −12.26 (19) | C1i—C4—C9—C10 | 51.84 (14) |
| C3—C2—C5—C6 | 167.92 (11) | C3i—C4—C9—C10 | −45.74 (13) |
| Symmetry code: (i) −x+1, −y+1, −z+1. |
Bernassau, J.-M., Bouillot, A., Fétizon, M., Hanna, I., Maia, E. R. & Prangé, T. (1987). J. Org. Chem. 52, 1993–2001.
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Masters, A. P., Parvez, M., Sorensen, T. S. & Sun, F. (1994). J. Am. Chem. Soc. 116, 2804–2811.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
Rauk, A., Sorensen, T. S. & Sun, F. (1995). J. Am. Chem. Soc. 117, 4506–4514.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Our research on the preparation and structure investigations of simple bicyclo[1.1.0]butanones (Rauk et al. 1995) led to the synthesis of the title compound. The stereochemistry of the title compound was not known at that time. In the title compound (Fig. 1), the central dioxane ring adopts a chair conformation with puckering parameters: Q = 0.3934 (11) Å, θ = 0.74 (1)° and φ = 0.0°. The four membered ring (C1/C2/C3/C4i; i = -x + 1, -y + 1, -z + 1) is slightly puckered with the dihedral angle between mean planes C1/C2/C3 and C1/C3/C4i being 13.50 (14)°. The molecular dimesions in the title compound agree very well with the corresponding molecular dimensions reported in closely related compounds (Masters et al., 1994; Bernassau et al., 1987). The crystal structure is devoid of any significant directional intermolecular interactions (Fig. 2).