Abstract
C15H17Br1O4, monoclinic, P21/n (no. 14), a = 7.1178(16) Å, b = 8.752(2) Å, c = 24.554(6) Å, β = 94.761(3)°, V = 1524.3(6) Å3, Z = 4, R gt (F) = 0.0275, wR ref (F2) = 0.0694, T = 296(2) K.
The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Colourless block |
| Size | 0.38 × 0.29 × 0.20 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 2.71 mm−1 |
| Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
| θmax, completeness: | 27.4°, 99% |
| N(hkl)measured, N(hkl)unique, Rint: | 16,555, 3433, 0.022 |
| Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 2728 |
| N(param)refined: | 184 |
| Programs: | Bruker [1], Olex2 [2], SHELX [3] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | Uiso*/Ueq |
|---|---|---|---|---|
| Br1 | 0.73838 (3) | 0.97872 (2) | 0.819505 (9) | 0.05928 (9) |
| O1 | 0.57986 (19) | 0.66873 (15) | 0.86998 (5) | 0.0530 (3) |
| O2 | 0.35401 (17) | 0.83786 (15) | 0.83102 (5) | 0.0474 (3) |
| O3 | 0.3568 (2) | 0.97624 (15) | 0.94541 (6) | 0.0581 (4) |
| O4 | 0.5005 (2) | 0.79176 (18) | 0.99440 (6) | 0.0644 (4) |
| H4 | 0.539 (4) | 0.864 (4) | 1.0136 (12) | 0.0966 (7)* |
| C1 | −0.0108 (4) | 0.7371 (4) | 0.96360 (11) | 0.0898 (9) |
| H1a | 0.0381 (4) | 0.8232 (13) | 0.9844 (7) | 0.1347 (13)* |
| H1b | −0.0786 (18) | 0.772 (2) | 0.93053 (11) | 0.1347 (13)* |
| H1c | −0.0943 (16) | 0.6802 (8) | 0.9847 (7) | 0.1347 (13)* |
| C2 | 0.1497 (3) | 0.6360 (3) | 0.94967 (9) | 0.0698 (6) |
| H2a | 0.2112 (3) | 0.5957 (3) | 0.98337 (9) | 0.0837 (8)* |
| H2b | 0.0981 (3) | 0.5501 (3) | 0.92840 (9) | 0.0837 (8)* |
| C3 | 0.3001 (3) | 0.7149 (2) | 0.91739 (7) | 0.0476 (4) |
| C4 | 0.4485 (3) | 0.5998 (2) | 0.90329 (8) | 0.0579 (5) |
| H4a | 0.3877 (3) | 0.5140 (2) | 0.88401 (8) | 0.0694 (6)* |
| H4b | 0.5147 (3) | 0.5615 (2) | 0.93665 (8) | 0.0694 (6)* |
| C5 | 0.4884 (3) | 0.7264 (2) | 0.82085 (7) | 0.0481 (4) |
| H5 | 0.4265 (3) | 0.6422 (2) | 0.80003 (7) | 0.0577 (5)* |
| C6 | 0.6352 (3) | 0.7959 (2) | 0.78838 (8) | 0.0456 (4) |
| C7 | 0.6869 (3) | 0.7331 (2) | 0.74293 (8) | 0.0492 (5) |
| H7 | 0.6177 (3) | 0.6463 (2) | 0.73254 (8) | 0.0591 (5)* |
| C8 | 0.8299 (3) | 0.7712 (2) | 0.70547 (7) | 0.0463 (4) |
| C9 | 0.9899 (3) | 0.8601 (3) | 0.71834 (9) | 0.0620 (6) |
| H9 | 1.0093 (3) | 0.9047 (3) | 0.75272 (9) | 0.0744 (7)* |
| C10 | 1.1197 (3) | 0.8823 (3) | 0.68044 (10) | 0.0693 (6) |
| H10 | 1.2262 (3) | 0.9414 (3) | 0.68959 (10) | 0.0831 (7)* |
| C11 | 1.0935 (3) | 0.8184 (2) | 0.62946 (9) | 0.0641 (6) |
| H11 | 1.1807 (3) | 0.8354 (2) | 0.60392 (9) | 0.0770 (7)* |
| C12 | 0.2130 (3) | 0.7812 (2) | 0.86365 (8) | 0.0510 (5) |
| H12a | 0.1277 (3) | 0.8635 (2) | 0.87127 (8) | 0.0612 (6)* |
| H12b | 0.1404 (3) | 0.7026 (2) | 0.84357 (8) | 0.0612 (6)* |
| C13 | 0.9377 (3) | 0.7288 (3) | 0.61626 (9) | 0.0615 (6) |
| H13 | 0.9199 (3) | 0.6843 (3) | 0.58183 (9) | 0.0738 (7)* |
| C14 | 0.8088 (3) | 0.7051 (2) | 0.65371 (8) | 0.0513 (5) |
| H14 | 0.7047 (3) | 0.6434 (2) | 0.64440 (8) | 0.0616 (6)* |
| C15 | 0.3902 (3) | 0.8413 (2) | 0.95313 (7) | 0.0428 (4) |
Source of material
The mixture of 2,2-bis(hydroxymethyl)butyric acid (1.0135 g, 6.8406 mmol), (Z)-2-bromo-3-phenylacrylaldehyde (1.5881 g, 7.5247 mmol), cyclohexane (10 mL), N,N-dimethylformamide (5 mL) and p-toluene sulfonic acid (0.0751 g, 0.3037 mmol) were refuxed for 4 h. After the mixture was cooled, sodium bicarbonate (0.0281 g, 0.3341 mmol) was added and stirred at room temperature for half an hour. The solvent was evaporated under reduced pressure and then ethyl acetate was added to dissolve the residue. Subsequently, the solution was washed with brine (20 mL × 2) and water (20 mL × 2), respectively. Then the organic layer was dried with anhydrous sodium sulfate, fltered. The product was recrystallized from n-hexane to aford colorless crystals (1.2930 g, 3.7897 mmol; yield 55.4%).
Experimental details
Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.
Comment
Acetal compounds have a wide application in organic syntheses, because they are used as a protection of carbonyl groups or intermediates [4, 5]. In addition, this type of compounds has insecticidal as well as anti-foaming properties [6, 7]. The crystal structures of some similar 1,3-dioxanes have been reported [8], [9], [10].
There is one crystallographically independent molecules in the asymmetric unit (see the figure). Molecules are pairwise hydrogen bonded to form dimeric units. All bond lengths and angles are in the expected ranges.
Funding source: Hunan University of Science and Engineering
Award Identifier / Grant number: 20XKY072
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: This work was supported by the general scientific research project of Hunan University of Science and Engineering (No. 20XKY072).
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
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© 2022 Guo-Kai Jia and Xian-You Yuan, published by De Gruyter, Berlin/Boston
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