Abstract
A new copper(II) complex [Cu(3,5,6-tcpa)(2,2′-bipy)Cl] (1) has been obtained through the one-pot hydrothermal reaction of copper chloride dihydrate with triclopyr (systematic name 2-((3,5,6-trichloropyridin-2-yl)oxy)acetic acid, abbreviation 3,5,6-Htcpa) and 2,2′-bipyridine (2,2′-bipy) coligands. 1 has crystallized in triclinic crystal system, P
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Author contributions: Jun-Xia Li: Conceptualization, Methodology, Software, Data curation, Writing – original draft, Writing – review & editing. Shuai Ge: Formal analysis. Yi-Jing Lu: Writing draft. Ke-Ying Quan: Software. Li-Bing Wu: Validation. Ai-Rong Wang: Resources, Review and editing.
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Research funding: This work was supported by Key Scientific Research Project of Colleges and Universities in Henan Province (No. 21A150036).
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Conflict of interest statement: The authors declare that they have no conflicts of interest.
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Code availability: Not applicable.
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Supplementary material: The CCDC number 2057591 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif.
References
1. Cho, S., Kim, J., Jeon, Y., Kim, T. H. Crystal structure of triclopyr. Acta Crystallogr. 2014, E70, o940. https://doi.org/10.1107/S160053681401681X.Search in Google Scholar PubMed PubMed Central
2. Gibson, D. J., Shupert, L. A., Liu, X. Do no harm: efficacy of a single herbicide application to control an invasive shrub while minimizing collateral damage to native species. Plants 2019, 8, 426. https://doi.org/10.3390/plants8100426.Search in Google Scholar PubMed PubMed Central
3. Anésio, A. H. C., Santos, M. V., Silveira, R. R., Ferreira, E. A., Santos, J. B. D., Silva, L. D. D. Persistence of auxinic herbicides applied on pasture and toxicity for succeeding crops. An Acad. Bras. Ciências 2018, 90, 1717–1732. https://doi.org/10.1590/0001-3765201820170134.Search in Google Scholar PubMed
4. Stern, A. R., Ben-Arie, R. Pre-harvest drop control of ‘red delicious’ and ‘Jonathan’ apple (Malus domestica) as affected by the synthetic auxin 3,5,6-TPA. J. Hortic. Sci. Biotechnol. 2006, 81, 943–948. https://doi.org/10.1080/14620316.2006.11512180.Search in Google Scholar
5. Turner, M. A., Gulsby, W. D., Harper, C. A. Mixture of triclopyr and imazapyr more effective than triclopyr alone for hardwood forest stand improvement. For. Sci. 2021, 67, 43–48. https://doi.org/10.1093/forsci/fxaa039.Search in Google Scholar
6. Barlow, S. M., TerryGehen, C. S., Corvaro, M. Developmental toxicity studies on triclopyr acid, triclopyr butoxyethyl ester and triclopyr triethylamine salt in the rabbit. Food Chem. Toxicol. 2022, 161, 112845. https://doi.org/10.1016/j.fct.2022.112845.Search in Google Scholar PubMed
7. Barlow, S. M., Terry, C., Gehen, S., Corvaro, M. Reproductive and developmental evaluations of triclopyr acid, triclopyr butoxyethyl ester and triclopyr triethylamine salt in the rat. Food Chem. Toxicol. 2022, 161, 112806. https://doi.org/10.1016/j.fct.2021.112806.Search in Google Scholar PubMed
8. Tayeb, M. A., Ismail, B. S., Khairiatul-Mardiana, J. Runoff of the herbicides triclopyr and glufosinate ammonium from oil palm plantation soil. Environ. Moint. Assess. 2017, 189, 551. https://doi.org/10.1007/s10661-017-6236-4.Search in Google Scholar PubMed
9. Maddila, S., Rana, S., Pagadala, R., Maddila, S. N., Vasam, C., Jonnalagadda, S. B. Ozone-driven photocatalyzed degradation and mineralization of pesticide, Triclopyr by Au/TiO2. J. Environ. Sci. Health B 2015, 50, 571–583. https://doi.org/10.1080/03601234.2015.1028835.Search in Google Scholar PubMed
10. Pozdnyakov, I. P., Snytnikova, O. A., Yanshole, V. V., Fedunov, R. G., Grivin, V. P., Plyusnin, V. F. Direct UV photodegradation of herbicide triclopyr in aqueous solutions: a mechanistic study. Chemosphere 2022, 293, 133573. https://doi.org/10.1016/j.chemosphere.2022.133573.Search in Google Scholar PubMed
11. Isoardi, K. Z., Page, C. B., Roberts, M. S., Isbister, G. K. Life-threatening triclopyr poisoning due to diethylene glycol monoethyl ether solvent. Clin. Toxicol. 2021, 59, 61–64. https://doi.org/10.1080/15563650.2020.1757103.Search in Google Scholar PubMed
12. Pandey, A., Sharma, S., Jain, R. Voltammetric sensor for the monitoring of hazardous herbicide triclopyr (TCP). J. Hazard Mater. 2019, 367, 246–255. https://doi.org/10.1016/j.jhazmat.2018.12.083.Search in Google Scholar PubMed
13. Kennard, C. H. L., Smith, G. (2-Chlorophenoxy)acetic acid. Acta Crystallogr. B 1981, 37, 1456–1458. https://doi.org/10.1107/S0567740881006274.Search in Google Scholar
14. Kumar, S. V., Rao, L. M. (4-Chlorophenoxy)acetic acid. Acta Crystallogr. B 1982, 38, 2062–2064. https://doi.org/10.1107/S0567740882007961.Search in Google Scholar
15. Smith, G., Kennard, C. H. L., White, A. H. (3,4-Dichlorophenoxy)acetic acid. Acta Crystallogr. B 1981, 37, 1454–1455. https://doi.org/10.1107/S0567740881006262.Search in Google Scholar
16. Smith, G., Kennard, C. L., White, A. H. Herbicides. II. Crystal structure of 2,4,5-T (2,4,5-trichlorophenoxyacetic acid). Aust. J. Chem. 1976, 29, 2727–2730. https://doi.org/10.1071/CH9762727.Search in Google Scholar
17. Smith, G., Kennard, C. H. L., White, A. H. The structure of 2,4,6-trichlorophenoxyacetic acid. Cryst. Struct. Commun. 1977, 6, 49–52.Search in Google Scholar
18. Mirosław, B., Mahmoudi, G., Ferenc, W., Cristóvão, B., Osypiuk, D., Sarzyński, J., Głuchowska, H., Franconetti, A., Frontera, A. Halogen interactions in dinuclear copper(II) 2,4-dibromophenoxyacetate: crystal structure and quantum chemical calculations. J. Mol. Struct. 2020, 1202, 127227. https://doi.org/10.1016/j.molstruc.2019.127227.Search in Google Scholar
19. Xu, X. L., Hu, F., Shuai, Q. Facile synthesis, crystal structure and bioactivity evaluation of two novel barium complexes based on 2,4,6-trichlorophenoxyacetic acid and o-ferrocenylcarbonyl benzoic acid. New J. Chem. 2017, 41, 13319–13326. https://doi.org/10.1039/c7nj03046k.Search in Google Scholar
20. Sharma, R. P., Saini, A., Kumar, J., Kumar, S., Venugopalan, P., Ferretti, V. Coordination complexes of copper(II) with herbicide-trichlorophenoxyacetate: syntheses, characterization, single crystal X-ray structure and packing analyses of monomeric [Cu(γ-pic)3(2,4,5-trichlorophenoxyacetate)]·H2O, [trans-Cu(en)2(2,4,5-trichlorophenoxy acetate)2]·2H2O and dimeric Cu2(H2tea)2(2,4,5-trichlorophenoxyacetate)2]·2(H2O). Inorg. Chim. Acta 2017, 457, 59–68. https://doi.org/10.1016/j.ica.2016.12.008.Search in Google Scholar
21. Qin, L., Li, Y., Liang, F. L., Li, L. J., Lan, Y. W., Li, Z. Y., Lu, X. T., Yang, M. Q., Ma, D. Y. A microporous 2D cobalt-based MOF with pyridyl sites and open metal sites for selective adsorption of CO2. Microporous Mesoporous Mater. 2022, 341, 112098. https://doi.org/10.1016/j.micromeso.2022.112098.Search in Google Scholar
22. Li, J. X., Xiong, L. Y., Fu, L. L., Bo, W. B., Du, Z. X., Feng, X. Structural diversity of Mn(II) and Cu(II) complexes based on 2-carboxyphenoxyacetate linker: syntheses, conformation comparison and magnetic properties. J. Solid State Chem. 2022, 305, 122636. https://doi.org/10.1016/j.jssc.2021.122636.Search in Google Scholar
23. Hu, P., Xiao, F. P., Wang, H. K., Rogach, A. L. Dual-functional hosts derived from metal- organic frameworks reduce dissolution of polyselenides and inhibit dendrite growth in a sodium-selenium battery. Energy Storage Mater. 2022, 51, 249–258. https://doi.org/10.1016/j.ensm.2022.06.019.Search in Google Scholar
24. Zhou, Z., Wang, Y., Peng, F., Meng, F., Zha, J., Ma, L., Du, Y., Peng, N., Ma, L., Zhang, Q., Gu, L., Yin, W., Gu, Z., Tan, C. Intercalation-activated layered MoO3 nanobelts as biodegradable nanozymes for tumor-specific photo-enhanced catalytic therapy. Angew. Chem. Int. Ed. 2022, 61, e202115939. https://onlinelibrary.wiley.com/doi/10.1002/anie.202115939.10.1002/anie.202115939Search in Google Scholar PubMed
25. Li, R. F., Zhang, H., Hong, M. Z., Shi, J. G., Liu, X. F., Feng, X. Two Co(II)/Ni(II) complexes based on nitrogenous heterocyclic ligand as high-performance electrocatalyst for hydrogen evolution reaction. Dalton Trans. 2022, 51, 3970–3976. https://doi.org/10.1039/D1DT03814A.Search in Google Scholar
26. Li, J. X., Zhang, T., Chen, H. J., Du, Z. X. A (4,4)-connected zinc(II) coordination polymer constructed with the flexible 2-carboxy phenoxyacetate ligand: synthesis, conformation alteration and fluorescent properties. Z. Kristallogr. 2021, 236, 251–259. https://doi.org/10.1515/zkri-2021-2043.Search in Google Scholar
27. Dang, L. L., Li, T. T., Zhang, T. T., Zhao, Y., Chen, T., Gao, X., Ma, L. F., Jin, G. X. Highly selective synthesis and near-infrared photothermal conversion of metalla-Borromean ring and [2]catenane assemblies. Chem. Sci. 2022, 13, 5130–5140. https://doi.org/10.1039/d2sc00437b.Search in Google Scholar PubMed PubMed Central
28. Li, R. F., Wang, M. Z., Liu, X. F., Feng, X. Near-infrared luminescence and magnetism of several lanthanide polymers by biphenyl carboxylic acid ligand. Inorg. Chim. Acta 2022, 539, 121029. https://doi.org/10.1016/j.ica.2022.121029.Search in Google Scholar
29. Li, J. X., Du, Z. X., Xiong, L. Y., Fu, L. L., Bo, W. B. Supramolecular isomerism in two nickel(II) coordination polymers constructed with the flexible 2-carboxyphenoxyacetate linker: syntheses, structure analyses and magnetic properties. J. Solid State Chem. 2021, 293, 121799. https://doi.org/10.1016/j.jssc.2020.121799.Search in Google Scholar
30. Hu, P., Xiao, F. P., Wu, Y. F., Yang, X. M., Li, N., Wang, H. K., Jia, J. F. Covalent encapsulation of sulfur in a graphene/N-doped carbon host for enhanced sodium-sulfur batteries. Chem. Eng. J. 2022, 443, 136257. https://doi.org/10.1016/j.cej.2022.136257.Search in Google Scholar
31. Li, J. X., Xia, Y. Q., Cheng, L. M., Feng, X. One-pot hydrothermal synthesis of a mononuclear cobalt(II) complex and an organic-inorganic supramolecular adduct: structures, properties and hirshfeld surface analyses. J. Solid State Chem. 2022, 313, 123271. https://doi.org/10.1016/j.jssc.2022.123271.Search in Google Scholar
32. Li, J. X., Xiong, L. Y., Xu, X. J., Liu, C., Wang, Z. G. The synthesis, crystal structure and conformation analysis of triclopyr ethyl ester. Z. Kristallogr. 2022, 237, 385–391. https://doi.org/10.1515/zkri-2022-0047.Search in Google Scholar
33. Zhang, C. L., Li, Y. L., Wang, T., Ju, Z. M., Zheng, H. G., Ma, J. Three different metal-organic frameworks derived from a one-pot crystallization and their controllable synthesis. Chem. Commun. 2015, 51, 8338–8341. https://doi.org/10.1039/c5cc01072a.Search in Google Scholar PubMed
34. zaman, A., Mohammad, M., Khan, S., Dutta, B., Maity, S., Naaz, S., Alam, S. M., Ghosh, P., Islam, M. M., Mir, M. H. One-pot crystallization of two 1,4-cyclohexanedicarboxylate- based tetranuclear Cu(II) compounds and their DNA binding affinities. CrystEngComm 2021, 23, 1091–1098. https://doi.org/10.1039/D0CE01734E.Search in Google Scholar
35. Chen, J. X. One-pot solvothermal crystallization of two three-dimensional manganese 2,6-naphthalenedicarboxylates: secondary ligand-induced pseudopolymorphism. Chem. Lett. 2011, 40, 886–887. https://doi.org/10.1246/cl.2011.886.Search in Google Scholar
36. Li, J. X., Du, Z. X., Wang, J., Feng, X. Two mononuclear zinc(II) complexes constructed by two types of phenoxyacetic acid ligands: syntheses, crystal structures and fluorescence properties. Z. Naturforsch. 2019, 74b, 839–845. https://doi.org/10.1515/znb-2019-0147.Search in Google Scholar
37. Li, J. X., Du, Z. X. A binuclear cadmium(II) cluster based on π⋯π stacking and halogen⋯halogen interactions: synthesis, crystal analysis and fluorescent properties. J. Cluster Sci. 2020, 31, 507–511. https://doi.org/10.1007/s10876-019-01666-w.Search in Google Scholar
38. Li, J. X., Du, Z. X., Zhang, L. L., Liu, D. L., Pan, Q. Y. Doubly mononuclear cocrystal and oxalato-bridged binuclear copper compounds containing flexible 2-((3,5,6-trichloro pyridin-2-yl)oxy)acetate tectons: synthesis, crystal analysis and magnetic properties. Inorg. Chim. Acta 2020, 512, 119890. https://doi.org/10.1016/j.ica.2020.119890.Search in Google Scholar
39. Li, J. X., Du, Z. X., Pan, Q. Y., Zhang, L. L., Liu, D. L. The first 3,5,6-trichloro pyridine-2-oxyacetate bridged manganese coordination polymer with features of π⋯π stacking and halogen⋯halogen interactions: synthesis, crystal analysis and magnetic properties. Inorg. Chim. Acta 2020, 509, 119677. https://doi.org/10.1016/j.ica.2020.119677.Search in Google Scholar
40. Du, Z. X., Li, J. X., Bai, R. F. Crystal structure of catena-poly[(μ2-4,4′-bipyridine-κ2N:N′)- tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dicobalt(II)], C19H10Cl6CoN3O6. Z. Kristallogr. - New Cryst. Struct. 2020, 235, 15–17. https://doi.org/10.1515/ncrs-2019-0434.Search in Google Scholar
41. Du, Z. X., Li, J. X., Bai, R. F. The crystal structure of catena-poly [(μ2-4,4′-bipyridine- κ2N:N′)-tetrakis(μ2-2-((3,5,6-trichloropyridin-2-yl)oxy)acetato-κ2O:O′)dinickel(II)], C19H10Cl6N3NiO6. Z. Kristallogr. - New Cryst. Struct. 2020, 235, 55–56. https://doi.org/10.1515/ncrs-2019-0470.Search in Google Scholar
42. Li, J. X., Du, Z. X., Bai, R. F. Crystal structure of aqua-bis(5-bromo-6-methyl-picolinato- κ2N,O)zinc(II) dihydrate, C14H16Br2N2O7Zn. Z. Kristallogr. - New Cryst. Struct. 2020, 235, 63–65. https://doi.org/10.1515/ncrs-2019-0486.Search in Google Scholar
43. Du, Z. X., Li, J. X. Crystal structure of tetraaqua-bis(2-((3,5,6-trichloropyridin-2-yl)oxy) acetato-κO)-nickel(II)—diaqua-bis(2-((3,5,6-trichloropyridin-2-yl)oxy)acetato)-nickel(II), C28H24Cl12N4Ni2O18. Z. Kristallogr. – New Cryst. Struct. 2020, 235, 881–883. https://doi.org/10.1515/ncrs-2020-0075.Search in Google Scholar
44. Li, J. X., Du, Z. X. The crystal structure of catena-poly[(μ2-4,4′-dipyridine-κ2N,N′)- bis(3,5,6-trichloropyridine-2-oxyacetato-κO)-bis(ethanol-κO)nickel(II)], C28H26Cl6N4NiO8. Z. Kristallogr. – New Cryst. Struct. 2020, 235, 887–890. https://doi.org/10.1515/ncrs-2020-0083.Search in Google Scholar
45. Li, J. X., Zhang, Y. H., Du, Z. X., Feng, X. One-pot solvothermal synthesis of mononuclear and oxalate-bridged binuclear nickel compounds: structural analyses, conformation alteration and magnetic properties. Inorg. Chim. Acta 2022, 530, 120697. https://doi.org/10.1016/j.ica.2021.120697.Search in Google Scholar
46. CrysAlis Pro . Rigaku Oxford Diffraction single crystal X-ray diffractometers; Rigaku Corporation: Wilmington, MA, 2016.Search in Google Scholar
47. 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. Crystallogr. 2009, 42, 339–341. https://doi.org/10.1107/S0021889808042726.Search in Google Scholar
48. Sheldrick, G. M. Shelxt – integrated space-group and crystal-structure determination. Acta Crystallogr. A 2015, 71, 3–8. https://doi.org/10.1107/S2053273314026370.Search in Google Scholar PubMed PubMed Central
49. Sheldrick, G. M., Crystal structure refinement with Shelxl, Acta Crystallogr. C 71 (2015) 3–8. https://doi.org/10.1107/S2053229614024218.Search in Google Scholar PubMed PubMed Central
50. Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Jayatilaka, D., Spackman, M. A. Crystal Explorer 2.0; University of Western Australia: Perth, Australia, 2007.Search in Google Scholar
51. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G., Taylor, R. J. J. Chem. Soc., Perkin Trans. 1987, 2, S1–S19.10.1039/p298700000s1Search in Google Scholar
52. McKinnon, J. J., Spackman, M. A., Mitchell, A. S. Novel tools for visualizing and exploring intermolecular interactions in molecular crystals. Acta Crystallogr. B 2004, 60, 627–668. https://doi.org/10.1107/S0108768104020300.Search in Google Scholar PubMed
53. Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J., Verschoor, G. C. Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2′-yl) -2,6-dithiaheptane]copper(II) perchlorate. J. Chem. Soc. Dalton Trans. 1984, 1349–1356. https://doi.org/10.1039/DT9840001349.Search in Google Scholar
54. Cavallo, G., Metrangolo, P., Milani, R., Pilati, T., Priimagi, A., Resnati, G., Terraneo, G. Chem. Rev. The Halogen Bond 2016, 116, 2478–2601. https://doi.org/10.1021/acs.chemrev.5b00484.Search in Google Scholar PubMed PubMed Central
55. Liu, C. Y., Lee, G. H., Wang, H. T. Synthesis, structural characterization and thermal stability of [Mn(3-bpd)2(NCS)2(H2O)2]·2H2O (1) and {[Mn(bpe)(NCS)2(H2O)2]·(3-bpd)·(bpe)·H2O}n (2) from one-pot crystallization. J. Chin. Chem. Soc. 2009, 56, 709–717. https://doi.org/10.1002/jccs.200900106.Search in Google Scholar
56. Zhong, K. L. Bis(1,10-phenanthroline-κ2N,N’)(sulfato-κ2O,O’)cobalt(II) propane-1,3-diol solvate. Acta Crystallogr. E. 2010, 66, m247. https://doi.org/10.1107/S1600536810003478.Search in Google Scholar PubMed PubMed Central
57. Du, Z. X., Li, J. X. The synthesis, structure and magnetic properties of a mononuclear cobalt compound with dipyrimidine sulfane ligand derived from 2-thio-barbituric acid. Inorg. Chim. Acta 2015, 436, 159–162. https://doi.org/10.1016/j.ica.2015.07.036.Search in Google Scholar
58. Liu, C. M., Zhang, D. Q., Hao, X., Zhu, D. B. Simultaneous assembly of mononuclear and dinuclear dysprosium(III) complexes behaving as single-molecule magnets in a one-pot hydrothermal synthesis. Sci. China Chem. 2017, 60, 358–365. https://doi.org/10.1007/s11426-016-0359-x.Search in Google Scholar
59. Du, Z. X., Li, J. X., Liu, S. J., Wang, Z. Q., Pan, Q. J. The syntheses, structures, and magnetic properties of two mononuclear manganese(II) complexes involving in situ hydrothermal decarboxylation. Z. Naturforsch. 2020, 75b, 567–575. https://doi.org/10.1515/znb-2020-0036.Search in Google Scholar
60. Ay, B., Sahin, O., Yildiz, E. One-pot hydrothermal synthesis of 1D copper (II) coordination polymers involving in-situ decarboxylation. Solid State Sci. 2019, 96, 105958. https://doi.org/10.1016/j.solidstatesciences.2019.105958.Search in Google Scholar
61. Zhang, X. M. Hydro(solvo)thermal in situ ligand syntheses. Coord. Chem. Rev. 2005, 249, 1201–1219. https://doi.org/10.1016/j.ccr.2005.01.004.Search in Google Scholar
62. Liang, Y. J., Feng, G., Zhang, X., Li, J. X., Jiang, Y. Bis(pyridyl) ancillary ligands and pyrazine sulfonic acid in the synthesis of two Ag(I) supramolecular structures and fluorescent properties of the latter. J. Struct. Chem. 2021, 62, 300–308; https://doi.org/10.1134/s0022476621020153.Search in Google Scholar
63. Zheng, Z., Xu, P., Jiang, Y., Liang, Y. J., Li, J. X. “Soft–hard” strategy to construct a pyrazine sulfonic acid copper(II) supramolecular structure and a study of its fluorescent property. J. Struct. Chem. 2021, 62, 292–299; https://doi.org/10.1134/s0022476621020141.Search in Google Scholar
64. Hu, H., Quan, J., Tan, Z., Fu, J. H., Liang, Y. J., Li, J. X. Synthesis and properties of dimercury(I) crystal network constructed with functionalized pyrazine sulfonate and nitrate linkers. Russ. J. Gen. Chem. 2021, 91, 910–914; https://doi.org/10.1134/S1070363221050224.Search in Google Scholar
65. Liang, Y. J., Hu, D., Zhang, L., Jiang, Y., Li, J. X. The synthesis and properties of a sodium supramolecular crystal network constructed with functional pyrazine sulfonic acid. J. Struct. Chem. 2021, 62, 1801–1809; https://doi.org/10.1134/S0022476621110172.Search in Google Scholar
Supplementary Material
This article contains supplementary material (https://doi.org/10.1515/zkri-2022-0063).
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