Abstract
C33H23Br2N5O4, triclinic, P1̄ (no. 2), a = 10.649(3) Å, b = 11.244(3) Å, c = 14.301(4) Å, α = 68.254(7)°, β = 72.939(7)°, γ = 81.125(7)°, V = 1518.5(7) Å3, Z = 2, Rgt(F) = 0.0514, wRref(F2) = 0.1327, T = 273(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.
Crystal: | Brown block |
Size: | 0.20 × 0.18 × 0.17 mm |
Wavelength: | MoKα radiation (0.71073 Å) |
μ: | 2.72 mm−1 |
Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
θmax, completeness: | 25.0°, 98 % |
N(hkl)measured, N(hkl)unique, Rint: | 12114, 5231, 0.059 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2σ(Iobs), 2863 |
N(param)refined: | 399 |
Programs: | Olex2 [1], Bruker [2], SHELX [3], Diamond [4] |
Atom | x | y | z | Uiso*/Ueq |
---|---|---|---|---|
Br1 | 0.08924 (5) | 0.65586 (6) | 1.00304 (6) | 0.1123 (3) |
Br2 | 0.32398 (6) | 0.92901 (5) | 0.50625 (6) | 0.0987 (3) |
O1 | 0.5868 (3) | 0.3468 (3) | 0.8911 (2) | 0.0584 (8) |
H1 | 0.6418 | 0.3915 | 0.8425 | 0.088* |
O2 | 1.1052 (3) | 0.3544 (3) | 0.6714 (3) | 0.0758 (10) |
O3 | 0.6299 (3) | 0.4212 (3) | 0.6078 (2) | 0.0550 (8) |
H3 | 0.5856 | 0.3658 | 0.6565 | 0.082* |
O4 | 0.6280 (3) | −0.0896 (3) | 0.8121 (3) | 0.0772 (10) |
N1 | 0.6907 (3) | 0.5610 (3) | 0.7584 (3) | 0.0451 (9) |
N2 | 0.8920 (3) | 0.4192 (3) | 0.6746 (3) | 0.0490 (9) |
H2 | 0.8150 | 0.3930 | 0.6873 | 0.059* |
N3 | 0.8292 (3) | 0.1690 (3) | 0.7443 (3) | 0.0481 (9) |
N4 | 0.5708 (3) | 0.1108 (3) | 0.8181 (3) | 0.0541 (10) |
H4 | 0.6017 | 0.1837 | 0.8037 | 0.065* |
N5 | 0.4164 (3) | 0.3208 (3) | 0.7444 (2) | 0.0408 (8) |
C1 | 0.2536 (4) | 0.4299 (5) | 1.0137 (4) | 0.0577 (12) |
H1A | 0.1805 | 0.3893 | 1.0636 | 0.069* |
C2 | 0.3672 (4) | 0.3587 (4) | 0.9890 (3) | 0.0542 (12) |
H2A | 0.3712 | 0.2703 | 1.0221 | 0.065* |
C3 | 0.4769 (4) | 0.4201 (4) | 0.9137 (3) | 0.0422 (10) |
C4 | 0.4709 (4) | 0.5526 (4) | 0.8636 (3) | 0.0412 (10) |
C5 | 0.5810 (4) | 0.6196 (4) | 0.7849 (3) | 0.0454 (10) |
H5 | 0.5719 | 0.7079 | 0.7527 | 0.054* |
C6 | 0.8001 (4) | 0.6273 (4) | 0.6828 (3) | 0.0441 (10) |
C7 | 0.9040 (4) | 0.5531 (4) | 0.6425 (3) | 0.0453 (10) |
C8 | 0.9911 (4) | 0.3299 (5) | 0.6867 (3) | 0.0538 (12) |
C9 | 0.9564 (4) | 0.1938 (4) | 0.7185 (3) | 0.0493 (11) |
C10 | 0.8016 (4) | 0.0463 (4) | 0.7717 (3) | 0.0497 (11) |
C11 | 0.6578 (5) | 0.0157 (4) | 0.8026 (3) | 0.0548 (12) |
C12 | 0.4333 (4) | 0.1017 (4) | 0.8562 (3) | 0.0448 (10) |
C13 | 0.3535 (4) | 0.2115 (4) | 0.8224 (3) | 0.0414 (10) |
C14 | 0.3583 (4) | 0.4319 (4) | 0.7197 (3) | 0.0426 (10) |
H14 | 0.2709 | 0.4425 | 0.7544 | 0.051* |
C15 | 0.4248 (4) | 0.5415 (4) | 0.6392 (3) | 0.0381 (9) |
C16 | 0.5573 (4) | 0.5333 (4) | 0.5868 (3) | 0.0405 (10) |
C17 | 0.6169 (4) | 0.6420 (4) | 0.5109 (3) | 0.0511 (11) |
H17 | 0.7048 | 0.6361 | 0.4755 | 0.061* |
C18 | 0.5481 (5) | 0.7576 (4) | 0.4874 (3) | 0.0562 (12) |
H18 | 0.5888 | 0.8300 | 0.4366 | 0.067* |
C19 | 0.2472 (4) | 0.5601 (5) | 0.9656 (4) | 0.0603 (13) |
C20 | 0.3531 (4) | 0.6221 (4) | 0.8913 (3) | 0.0536 (12) |
H20 | 0.3471 | 0.7107 | 0.8591 | 0.064* |
C21 | 1.0567 (5) | 0.0995 (5) | 0.7211 (4) | 0.0686 (14) |
H21 | 1.1438 | 0.1203 | 0.7036 | 0.082* |
C22 | 1.0256 (5) | −0.0252 (5) | 0.7497 (4) | 0.0796 (17) |
H22 | 1.0913 | −0.0904 | 0.7518 | 0.096* |
C23 | 0.8967 (5) | −0.0523 (5) | 0.7751 (4) | 0.0696 (14) |
H23 | 0.8734 | −0.1361 | 0.7944 | 0.084* |
C24 | 0.4177 (5) | 0.7659 (4) | 0.5397 (4) | 0.0548 (12) |
C25 | 0.3556 (4) | 0.6608 (4) | 0.6144 (3) | 0.0478 (11) |
H25 | 0.2676 | 0.6684 | 0.6488 | 0.057* |
C26 | 0.2184 (4) | 0.2061 (4) | 0.8665 (3) | 0.0532 (12) |
H26 | 0.1642 | 0.2791 | 0.8465 | 0.064* |
C27 | 0.1637 (5) | 0.0952 (5) | 0.9387 (4) | 0.0619 (13) |
H27 | 0.0732 | 0.0933 | 0.9669 | 0.074* |
C28 | 0.2430 (5) | −0.0134 (5) | 0.9695 (4) | 0.0643 (13) |
H28 | 0.2056 | −0.0891 | 1.0174 | 0.077* |
C29 | 0.3767 (5) | −0.0102 (4) | 0.9298 (3) | 0.0585 (12) |
H29 | 0.4299 | −0.0831 | 0.9523 | 0.070* |
C30 | 1.0172 (4) | 0.6125 (5) | 0.5700 (3) | 0.0544 (12) |
H30 | 1.0869 | 0.5635 | 0.5430 | 0.065* |
C31 | 1.0248 (5) | 0.7427 (5) | 0.5390 (4) | 0.0624 (13) |
H31 | 1.0999 | 0.7817 | 0.4911 | 0.075* |
C32 | 0.9227 (5) | 0.8156 (5) | 0.5780 (4) | 0.0684 (14) |
H32 | 0.9288 | 0.9038 | 0.5563 | 0.082* |
C33 | 0.8112 (5) | 0.7592 (4) | 0.6491 (4) | 0.0589 (12) |
H33 | 0.7424 | 0.8098 | 0.6750 | 0.071* |
1 Source of materials
In a 100 mL three necked flask, N2,N6-bis(2-aminophenyl)pyridine-2,6-dicarboxamide (0.69 g, 2 mmol), 5-bromo-2-hydroxybenzaldehyde (0.80 g, 4 mmol) and 60 mL ethanol solution were added, heated and refluxed for 7 h, cooled to room temperature to precipitate a yellow powder, filtered under reduced pressure, washed with ethanol for 4 times, and dried in vacuum. A yellow solid weighing 1.03 g was obtained with a yield of 72 %. Take 0.1 g of solid into a 25 mL beaker, add 10 mL chloroform, stir and dissolve it, let it stand still at room temperature and volatilize it naturally for 9 days, and then precipitate crystals.
2 Experimental details
Using Olex2 [1], the structure was solved using charge flipping and refined with the ShelXL [3] refinement. All hydrogen atoms were positioned geometrically, with the d(C–H) = 0.97–0.99 Å, Uiso(H) = 1.2 times Ueq(C) and Uiso(H) = 1.5 times Ueq(O).
3 Comment
Schiff bases are a class of organic compounds formed by the condensation of amines and active carbonyl groups, which contain imine or imine characteristic groups. They are widely used in metal ion recognition and construction of coordination compounds [5]. Schiff bases and their metal complexes have important application prospects in catalysis, analytical chemistry, medicine, corrosion, photochromism, and other fields [6, 7]. N2,N6-bis (2-aminophenyl) pyridine-2,6-dicarboxamide is widely used for metal ion recognition and the construction of Schiff base complexes due to its presence of multiple nitrogen atoms and the presence of multiple coordination atoms in the Schiff base formed by condensation reaction with aldehydes [8, 9]. The single crystal structure shows that the two amino groups have undergone a condensation reaction with the aldehyde group of 5-bromo-2-hydroxybenzaldehyde. The bond length of N2=C7 is 1.416(5) Å, and the bond length of N4=C12 is 1.411(5) Å [10, 11]. There are O1–H1⋯N1, O3–H3⋯N5, N2–H2⋯O3 and N4–H4⋯O1 intramolecular hydrogen bonds in the molecule.
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Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: None declared.
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Search in Google Scholar
2. Bruker. APEX2, SAINT and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2012.Search in Google Scholar
3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar
4. Brandenburg, K. Diamond. Visual Crystal Structure Information System. (version 4.0); Crystal Impact, Bonn, Germany, 2015.Search in Google Scholar
5. Zhao, W. Z. Crystal structure of N2,N6-bis(2-(((E)-quinolin-8-ylmethylene)amino)phenyl) pyridine-2,6-dicarboxamide, C39H27N7O2. Z. Kristallogr. N. Cryst. Struct. 2022, 237, 1013–1015; https://doi.org/10.1515/ncrs-2022-0338.Search in Google Scholar
6. Shen, L. Y., Chen, X. L., Yang, X. J., Xu, H., Huang, Y. L., Zhang, X., Redshaw, C., Zhang, Q. L. A highly selective turn-on fluorescent probe for the detection of zinc. Molecules 2021, 26, 1233; https://doi.org/10.3390/molecules26133825.Search in Google Scholar PubMed PubMed Central
7. Zhong, X., Li, Z. K., Shi, R. F., Yan, L., Zhu, Y. H., Li, H. Schiff base-modified nanomaterials for ion detection: a review. ACS Appl. Nano Mater. 2022, 5, 13998–14020; https://doi.org/10.1021/acsanm.2c03477.Search in Google Scholar
8. Zhang, X., Wu, S. T., Yang, X. J., Shen, L. Y., Huang, Y. L., Xu, H., Zhang, Q. L., Sun, T., Redshaw, C., Feng, X. Dynamic coordination between atriphenylamine-functionalized salicylaldehyde Schiff base and a copper(II) ion. Inorg. Chem. 2021, 60, 8581–8591; https://doi.org/10.1021/acs.inorgchem.1c00523.Search in Google Scholar PubMed
9. Shen, L. Y., Yu, C. J., Xie, H. F., Xu, N., Xu, H., Huang, Y. L., Redshaw, C., Feng, X., Zhang, Q. L. Naphthaldehyde-based Schiff base dyes: aggregation-induced emission and high-contrast reversible mechanochromic luminescence. Mater. Chem. Front. 2022, 6, 2491–2498; https://doi.org/10.1039/d2qm00542e.Search in Google Scholar
10. Yang, J., Xu, J., Liao, N., Wu, Q. [2,2′-{ethane-1,2-diylbis[(azanylylidene) methanylylidene]}bis(3-bromo-2-hydroxyphenyl)]iron(III) nitrate, C20H12Br2CuN2O2. Z. Kristallogr. N. Cryst. Struct. 2022, 237, 1091–1092, https://doi.org/10.1515/ncrs-2022-0297.Search in Google Scholar
11. Kumar, N., Asatkar, A. K., Panda, S., Zade, S. S. Synthesis, characterization and supramolecular building motifs of substituted salphen- and thiasalphen-metal complexes. Polyhedron 2016, 117, 718–728; https://doi.org/10.1016/j.poly.2016.06.050.Search in Google Scholar
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