Abstract
C16H19ClO6, triclinic, P1̅ (no. 2), a = 7.905(3) Å, b = 9.194(4) Å, c = 13.094(5) Å, α = 99.928(4)°, β = 105.341(4)°, γ = 109.283(4)°, V = 830.2(6) Å3, Z = 2, Rgt(F) = 0.0343, wRref(F2) = 0.0898, T = 296(2)K.
The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Block, colorless |
| Size: | 0.42 × 0.40 × 0.36 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 0.26 mm−1 |
| Diffractometer, scan mode: | Bruker SMART, φ and ω-scans |
| 2θmax, completeness: | 50°, >99% |
| N(hkl)measured, N(hkl)unique, Rint: | 7794, 2918, 0.018 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 2685 |
| N(param)refined: | 211 |
| Programs: | Bruker programs [1], SHELX [2, 3] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| Cl1 | 0.07422(8) | 0.25949(7) | 0.94239(4) | 0.0747(2) |
| O1 | −0.45979(15) | 0.05796(11) | 1.25129(8) | 0.0441(3) |
| O2 | −0.42244(14) | 0.32241(11) | 1.26091(8) | 0.0403(2) |
| O3 | −0.86012(15) | 0.13316(18) | 1.38751(11) | 0.0709(4) |
| O4 | −0.63109(14) | 0.21825(12) | 1.55315(8) | 0.0450(3) |
| O5 | −0.26490(15) | 0.17232(13) | 1.50798(9) | 0.0507(3) |
| O6 | −0.26856(13) | 0.41872(11) | 1.52970(8) | 0.0431(3) |
| C1 | −0.3431(2) | 0.18110(16) | 1.12498(11) | 0.0400(3) |
| C2 | −0.1998(2) | 0.12440(18) | 1.14777(12) | 0.0459(4) |
| H2 | −0.1881 | 0.0713 | 1.2020 | 0.055* |
| C3 | −0.0735(2) | 0.14611(19) | 1.09042(13) | 0.0495(4) |
| H3 | 0.0223 | 0.1072 | 1.1055 | 0.059* |
| C4 | −0.0910(2) | 0.22587(18) | 1.01089(12) | 0.0479(4) |
| C5 | −0.2339(3) | 0.2809(2) | 0.98523(13) | 0.0546(4) |
| H5 | −0.2455 | 0.3330 | 0.9304 | 0.066* |
| C6 | −0.3604(2) | 0.2577(2) | 1.04230(13) | 0.0513(4) |
| H6 | −0.4584 | 0.2939 | 1.0252 | 0.062* |
| C7 | −0.4760(2) | 0.16675(16) | 1.18987(11) | 0.0405(3) |
| H7 | −0.6078 | 0.1284 | 1.1393 | 0.049* |
| C8 | −0.5823(2) | 0.03951(17) | 1.31508(12) | 0.0435(3) |
| H8A | −0.5649 | −0.0344 | 1.3575 | 0.052* |
| H8B | −0.7143 | −0.0055 | 1.2661 | 0.052* |
| C9 | −0.5454(2) | 0.32040(17) | 1.32363(12) | 0.0398(3) |
| H9A | −0.6753 | 0.2874 | 1.2741 | 0.048* |
| H9B | −0.5059 | 0.4276 | 1.3714 | 0.048* |
| C10 | −0.53787(18) | 0.20298(16) | 1.39407(11) | 0.0358(3) |
| C11 | −0.34170(18) | 0.25997(16) | 1.48304(11) | 0.0353(3) |
| C12 | −0.6956(2) | 0.18094(17) | 1.44417(13) | 0.0426(3) |
| C13 | −0.0854(2) | 0.4846(2) | 1.62007(14) | 0.0542(4) |
| H13A | −0.0288 | 0.6004 | 1.6345 | 0.065* |
| H13B | 0.0004 | 0.4412 | 1.5984 | 0.065* |
| C14 | −0.1074(3) | 0.4454(2) | 1.72299(14) | 0.0669(5) |
| H14A | −0.1483 | 0.3315 | 1.7117 | 0.100* |
| H14B | −0.2009 | 0.4798 | 1.7409 | 0.100* |
| H14C | 0.0128 | 0.4999 | 1.7826 | 0.100* |
| C15 | −0.7760(3) | 0.1840(3) | 1.60595(16) | 0.0654(5) |
| H15A | −0.8399 | 0.0689 | 1.5921 | 0.078* |
| H15B | −0.8709 | 0.2251 | 1.5761 | 0.078* |
| C16 | −0.6793(3) | 0.2631(2) | 1.72671(16) | 0.0700(5) |
| H16A | −0.6218 | 0.3774 | 1.7398 | 0.105* |
| H16B | −0.5823 | 0.2248 | 1.7550 | 0.105* |
| H16C | −0.7712 | 0.2380 | 1.7632 | 0.105* |
Source of material
Diethyl 2,2-bis(hydroxymethyl)malonate (2.64 g, 12 mmol), 4-chlorobenzaldehyde (1.41 g, 10 mmol) and nanosolid superacid SO42−/Fe2O3 (0.1 g) were added into a mixture of N,N-dimethylformamide (12 mL) and cyclohexane (8 mL) and refluxed for 4 h at 378 K with stirring. After workup, the reaction mixture was filtrated and the organic layer was washed with water (10×3 mL) and then dried over Na2SO4. Then the white powder (2.43 g, yield 71%) was isolated after filtration and evaporation. The product was recrystallized from ethyl acetate to afford colorless crystals.
Experimental details
All hydrogen atoms were identified in difference Fourier syntheses. The Uiso values of the hydrogen atoms of methyl groups were set to 1.5Ueq(C) and the Uiso values of all other hydrogen atons were set to 1.2Ueq(C).
Discussion
1,3-Dioxane compounds of the main group elements are intriguing structurally due to the variety of 1,3-dioxane ring bonding modes which they display [4]. We previously synthesized a series of acetal compounds [5, 6] .
A new acetal compound was synthesized and characterized by single-crystal X-ray diffraction [2, 3] . In the 1,3-dioxane ring, the bond lengths of O1–C7 and O2–C7 are 1.4039(17) Å and 1.4257(18) Å, respectively. All geometric parameters are in the expected ranges for this class of compounds [7, 8]
Acknowledgements
This work was financially supported by the Scientific Research Fund of Hunan Provincial Education Department (no. 16B104), the Opening Project of Key Laboratory of Comprehensive Utilization of Advantage Plants Resources in Hunan South (no. XNZW16C01) and the Scientific Research Fund of Hunan University of Science and Engineering (no. 16XKY063), Natural Science Foundation of Hunan Province of China (2017JJ3093).
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©2017 Xian-You Yuan et al., published by De Gruyter, Berlin/Boston
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