Abstract
C11H16BrNO5, monoclinic, P21/c (no. 14), a = 15.164(7) Å, b = 11.798(5) Å, c = 7.359(3) Å, β = 90.792°, V = 1316.4(10) Å3, Z = 4, R gt (F) = 0.0322, wR ref (F 2) = 0.0797, 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: | Yellow block |
| Size: | 0.40 × 0.36 × 0.30 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 3.14 mm−1 |
| Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
| θ max, completeness: | 27.5°, >99% |
| N(hkl)measured, N(hkl)unique, R int: | 14,460, 2974, 0.026 |
| Criterion for I obs, N(hkl)gt: | I obs > 2 σ(I obs), 2400 |
| N(param)refined: | 169 |
| Programs: | Bruker [1], SHELX [2, 3] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | U iso*/U eq |
|---|---|---|---|---|
| Br1 | 0.85816 (2) | 0.21106 (3) | 0.04114 (4) | 0.05558 (12) |
| C1 | 1.12451 (14) | 0.21342 (18) | 0.1810 (3) | 0.0316 (4) |
| O2 | 1.43527 (12) | 0.22951 (14) | 0.3232 (3) | 0.0513 (5) |
| H2 | 1.483797 | 0.225630 | 0.275730 | 0.077* |
| O4 | 1.37491 (11) | −0.11326 (13) | 0.4182 (2) | 0.0423 (4) |
| H4 | 1.369792 | −0.172813 | 0.361542 | 0.063* |
| O3 | 1.31134 (12) | −0.01634 (14) | −0.0275 (2) | 0.0448 (4) |
| H3 | 1.287561 | 0.031911 | −0.091665 | 0.067* |
| O1 | 1.22465 (11) | 0.36110 (13) | 0.2597 (2) | 0.0424 (4) |
| N1 | 1.26999 (11) | 0.14885 (15) | 0.2515 (2) | 0.0309 (4) |
| H1 | 1.283343 | 0.218463 | 0.273074 | 0.037* |
| C5 | 0.97406 (14) | 0.2590 (2) | 0.1071 (3) | 0.0372 (5) |
| C2 | 1.14633 (15) | 0.33010 (19) | 0.2115 (3) | 0.0338 (5) |
| O5 | 1.38540 (13) | −0.18430 (14) | 0.7675 (2) | 0.0454 (4) |
| H5A | 1.362167 | −0.134469 | 0.835257 | 0.068* |
| H5B | 1.376889 | −0.166396 | 0.656646 | 0.068* |
| C7 | 1.18961 (14) | 0.12808 (18) | 0.2029 (3) | 0.0337 (5) |
| H7 | 1.173491 | 0.053201 | 0.181030 | 0.040* |
| C8 | 1.34078 (13) | 0.06529 (17) | 0.2737 (3) | 0.0302 (4) |
| C6 | 1.03874 (14) | 0.1801 (2) | 0.1293 (3) | 0.0355 (5) |
| H6 | 1.026180 | 0.103875 | 0.110268 | 0.043* |
| C3 | 1.07591 (17) | 0.4086 (2) | 0.1847 (3) | 0.0433 (6) |
| H3A | 1.086551 | 0.485563 | 0.201557 | 0.052* |
| C11 | 1.30454 (15) | −0.03947 (19) | 0.3700 (3) | 0.0372 (5) |
| H11A | 1.273483 | −0.016588 | 0.478326 | 0.045* |
| H11B | 1.263163 | −0.078578 | 0.290220 | 0.045* |
| C9 | 1.41180 (15) | 0.1213 (2) | 0.3926 (3) | 0.0413 (5) |
| H9A | 1.390156 | 0.129727 | 0.515326 | 0.050* |
| H9B | 1.463637 | 0.073173 | 0.397594 | 0.050* |
| C4 | 0.99268 (16) | 0.3734 (2) | 0.1347 (3) | 0.0437 (6) |
| H4A | 0.948079 | 0.426755 | 0.119081 | 0.052* |
| C10 | 1.37661 (15) | 0.0359 (2) | 0.0861 (3) | 0.0385 (5) |
| H10A | 1.397303 | 0.104618 | 0.028085 | 0.046* |
| H10B | 1.426498 | −0.014919 | 0.100265 | 0.046* |
Source of material
5-Bromosalicylaldehyde (1.01 g, 5 mmol), tris(hydroxymethyl)methyl aminomethane (0.67 g, 5.5 mmol) and ethanol (15 mL) were heated and stirred at 373 K for 8 h, then cooled to room temperature; then the product was filtered off and recrystallized from ethanol to afford yellow crystals (1.28 g, yield 89%).
Experimental details
All hydrogen atoms were identified in difference Fourier syntheses. The U iso values of the hydrogen atoms of methyl groups and amino group were set to 1.5U eq (C) and the U iso values of all other hydrogen atoms were set to 1.2U eq (C).
Comment
Schiff bases have a wide range of applications in catalysis, medicine, functional materials and corrosion resistance [4], [5], [6]. In recent years, salicylaldehyde Schiff base compounds have attracted extensive attention due to their unique structure and properties [7], [8], [9], [10], [11].
The structure of the target molecule without a water molecule had been reported [12]. The asymmetric unit of the title structure contains one target molecule and one water molecule. It can be clearly observed that the title molecule exists in a keto form in the structure. The NH group of the enamine moiety participates in an intramolecular N–H···O hydrogen bond (N1···O1 = 2.598 Å) to the oxygen atom of the keto group. The OH group of the TRIS moiety is involved in a OH···O hydrogen bond (O3···O1′ = 2.735 Å; ′ = x, −y+1/2, z−1/2). The water molecule donates in total two hydrogen bonds to two title target molecules (O5···O4 = 2.639 Å; O5···O2″ = 2.859 Å; ″ = −x+3, −y, −z+1).
Funding source: Natural Science Foundation of Hunan Province of China
Award Identifier / Grant number: 2021JJ30291
Funding source: Scientific Research Fund of Hunan Provincial Education Department
Award Identifier / Grant number: 21A0518
Award Identifier / Grant number: 21C0691
Funding source: Undergraduate Training Program for Innovation and Entrepreneurship of Hunan Province of China
Award Identifier / Grant number: [2021]197-3585
Funding source: Undergraduate Training Program for Innovation and Entrepreneurship of Hunan University of Science and Engineering
Award Identifier / Grant number: 2021
Funding source: Yongzhou Guiding Science and Technology Plan
Award Identifier / Grant number: 2021
Funding source: Hunan University of Science and Engineering
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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 financially supported by Natural Science Foundation of Hunan Province of China (2021JJ30291), the Scientific Research Fund of Hunan Provincial Education Department (21A0518, 21C0691), Undergraduate Training Program for Innovation and Entrepreneurship of Hunan Province of China ([2021]197-3585), Undergraduate Training Program for Innovation and Entrepreneurship of Hunan University of Science and Engineering (2021), Yongzhou Guiding Science and Technology Plan (2021), the construct program of applied characteristic discipline in Hunan University of Science and Engineering.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
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© 2022 Hai-Bo Qin et al., published by De Gruyter, Berlin/Boston
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