European Journal of Chemistry

Synthesis and crystal structure of the copper (II) carboxylate with 2,2-bipyridine, [Cu(4-mba)2(bipy)(H2O)]

Crossmark


Main Article Content

Sibel Demir Kanmazalp
Adnan Qadir
Necmi Dege

Abstract

The new Cu(II) carboxylate complex, aqua(2,2'-bipyridine-κ2N,N')bis(4-methylbenzoato-κO)copper(II) [Cu(4-mba)2(bipy)(H2O)] (4-mba: 4-methylbenzoate, bipy: 2,2'-bipyridine) was synthesized, and the molecular structure of the complex was characterized by the single crystal X-ray diffraction technique. The X-ray diffraction analysis indicated that the asymmetric unit comprises an independent molecule. Crystal data for [Cu(4-meb)2(2,2-bipy)(H2O)]: Triclinic, space group P-1 (no. 2), a = 7.0452(13) Å, b = 11.260(2) Å, c = 16.635(3) Å, α = 103.543(7)°, β = 91.002(7)°, γ = 104.106(6)°, = 1240.4(4) Å3, Z = 2, T = 296 K, μ(MoKα) = 0.918 mm-1, Dcalc = 1.360 g/cm3, 51364 reflections measured (5.054° ≤ 2Θ ≤ 57.38°), 6258 unique (Rint = 0.0398, Rsigma = 0.0284) which were used in all calculations. The final R1 was 0.0392 (I > 2σ(I)) and wR2 was 0.1021 (all data). The Cu(II) ion was found to be coordinated with two nitrogen atoms of the 2,2'-bipyridine ligand, two oxygen atoms of the 4-methyl benzoate molecule, and one oxygen atom of the aqua ligand. In the three-dimensional supramolecular architecture, molecules are connected through pairs of O-H···O and C-H···O intermolecular interactions, consisting of chains. The molecule also demonstrates Cg···Cg intermolecular interactions between six-membered rings of 2,2'-bipyridine.


icon graph This Abstract was viewed 390 times | icon graph Article PDF downloaded 255 times icon graph Article CIF FILE downloaded 0 times

How to Cite
(1)
Kanmazalp, S. D.; Qadir, A.; Dege, N. Synthesis and Crystal Structure of the Copper (II) Carboxylate With 2,2-Bipyridine, [Cu(4-mba)2(bipy)(H2O)]. Eur. J. Chem. 2023, 14, 109-113.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Jennifer, S. J.; Muthiah, P. T. Synthesis, crystal structures and supramolecular architectures of square pyramidal Cu(II) complexes containing aromatic chelating N,N'-donor ligands. Chemistry Central Journal 2014, 8, 42.
https://doi.org/10.1186/1752-153X-8-42

[2]. Liu, F.-Y.; Zhang, M.-H.; Kou, J.-F. (2,2'-Bi-pyridine-κ(2) N,N')bis-(nitrato-κ(2) O,O')copper(II). Acta Crystallogr. Sect. E Struct. Rep. Online 2013, 69, m609.
https://doi.org/10.1107/S1600536813028201

[3]. Atria, A. M.; Cortés, P.; Acevedo, L.; Trujillo, R.; Manzur, J.; Peña, O.; Baggio, R. PREPARATION, STRUCTURE AND PROPERTIES OF BIS (M2-CHLORO)-(NITRATO-O)-(2,2'-BIPYRIDINE-N.n')­COPPER(II):[cu(2,2'-BP)cl NO3]2. J. Chil. Chem. Soc. 2004, 49, 341-344.
https://doi.org/10.4067/S0717-97072004000400013

[4]. Cody, C. C.; Kelly, H. R.; Mercado, B. Q.; Batista, V. S.; Crabtree, R. H.; Brudvig, G. W. Distorted copper(II) complex with unusually short CF···Cu distances. Inorg. Chem. 2021, 60, 14759-14764.
https://doi.org/10.1021/acs.inorgchem.1c01958

[5]. Kansız, S.; Qadir, A. M.; Dege, N.; Faizi, S. H. Two new copper (II) carboxylate complexes based on N,N,N',N'-tetramethylethyleneamine: Synthesis, crystal structures, spectral properties, dft studies and hirshfeld surface analysis. J. Mol. Struct. 2021, 1230, 129916.
https://doi.org/10.1016/j.molstruc.2021.129916

[6]. Llases, M.-E.; Morgada, M. N.; Vila, A. J. Biochemistry of copper site assembly in heme-copper oxidases: A theme with variations. Int. J. Mol. Sci. 2019, 20, 3830-3848.
https://doi.org/10.3390/ijms20153830

[7]. Abdul-Ghani, A.-S.; Abu-Hijleh, A. L.; Qazzaz, M. Effect of bis(acetato)tetrakis(imidazole) copper(II) in delaying the onset and reducing the mortality rate of strychnine- and thiosemicarbazide- induced convulsions. Biol. Trace Elem. Res. 2004, 101, 87-95.
https://doi.org/10.1385/BTER:101:1:87

[8]. Gawlig, C.; Jung, J.; Mollenhauer, D.; Schindler, S. Synthesis and characterization of copper complexes with tripodal ligands bearing amino acid groups. Z. Anorg. Allg. Chem. 2021, 647, 951-959.
https://doi.org/10.1002/zaac.202000320

[9]. Valentine, J. S.; Mota de Freitas, D. Copper-zinc superoxide dismutase: A unique biological "ligand" for bioinorganic studies. J. Chem. Educ. 1985, 62, 990-997.
https://doi.org/10.1007/978-1-349-17889-6_19

[10]. Batool, S. S.; Ahmad, S.; Khan, I. U.; Ejaz; Harrison, W. T. A. Structural characterization of a new copper(II) complex of 1,10-phenanthroline and benzoate [Cu(phen)(C6H5CO 2 − )2]. J. Struct. Chem. 2015, 56, 387-391.
https://doi.org/10.1134/S0022476615020286

[11]. Mojumdar, S. C.; Madgurambal, G.; Saleh, M. T. A study on synthesis and thermal, spectral and biological properties of carboxylato-Mg(II) and carboxylato-Cu(II) complexes with bioactive ligands. J. Therm. Anal. Calorim. 2005, 81, 205-210.
https://doi.org/10.1007/s10973-005-0768-5

[12]. Kozlevčar, B.; Leban, I.; Turel, I.; Šegedin, P.; Petric, M.; Pohleven, F.; White, A. J. P.; Williams, D. J.; Sieler, J. Complexes of copper (II) acetate with nicotinamide: preparation, characterization and fungicidal activity; crystal structures of [Cu2 (O2CCH3)4 (nia)] and [Cu2 (O2CCH3)4 (nia)2]. Polyhedron 1999, 18, 755-762.
https://doi.org/10.1016/S0277-5387(98)00350-7

[13]. Ranford, J. D.; Sadler, P. J.; Tocher, D. A. Cytotoxicity and antiviral activity of transition-metal salicylato complexes and crystal structure of Bis(diisopropylsalicylato)(1,10-phenanthroline)copper(II). J. Chem. Soc., Dalton Trans. 1993, 3393.
https://doi.org/10.1039/dt9930003393

[14]. Devereux, M.; O'Shea, D.; O'Connor, M.; Grehan, H.; Connor, G.; McCann, M.; Rosair, G.; Lyng, F.; Kellett, A.; Walsh, M.; Egan, D.; Thati, B. Synthesis, catalase, superoxide dismutase and antitumour activities of copper(II) carboxylate complexes incorporating benzimidazole, 1,10-phenanthroline and bipyridine ligands: X-ray crystal structures of [Cu(BZA)2(bipy)(H2O)], [Cu(SalH)2(BZDH)2] and [Cu(CH3COO)2 (5,6-DMBZDH)2] (SalH2=salicylic acid; BZAH=benzoic acid; BZDH = benzimidazole and 5,6-DMBZDH=5,6-dimethyl benzimidazole). Polyhedron 2007, 26, 4073-4084.
https://doi.org/10.1016/j.poly.2007.05.006

[15]. Farrugia, L. J. WinGXsuite for small-molecule single-crystal crystallography. J. Appl. Crystallogr. 1999, 32, 837-838.
https://doi.org/10.1107/S0021889899006020

[16]. Sheldrick, G. M. (1996). SHELXS97 and SHELXL97. University of Göttingen, Germany.

[17]. Spek, A. L. PLATON SQUEEZE: a tool for the calculation of the disordered solvent contribution to the calculated structure factors. Acta Crystallogr. C Struct. Chem. 2015, 71, 9-18.
https://doi.org/10.1107/S2053229614024929

[18]. Spek, A. L. checkCIF validation ALERTS: what they mean and how to respond. Acta Crystallogr. E Crystallogr. Commun. 2020, 76, 1-11.
https://doi.org/10.1107/S2056989019016244

[19]. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. Mercury: visualization and analysis of crystal structures. J. Appl. Crystallogr. 2006, 39, 453-457.
https://doi.org/10.1107/S002188980600731X

[20]. 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

[21]. Abedi, A.; Mehri-Lighvan, Z.; Yasan, M.; Amani, V. Novel Cu(II) complexes of bithiazole: structure and biological study. J. Iran. Chem. Soc. 2017, 14, 491-502.
https://doi.org/10.1007/s13738-016-0997-5

[22]. Su, C.-C.; Lin, Y.-L.; Liu, S.-J.; Chang, T.-H.; Wang, S.-L.; Liao, F.-L. Bonding properties of copper(II)-N chromophores: Molecular and electronic structures of copper(II) complexes containing ethylenediamine and heterocyclic diimine ligands. Polyhedron 1993, 12, 2687-2696.
https://doi.org/10.1016/S0277-5387(00)80119-9

[23]. 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

[24]. Pirsiavash, F.; Amani, V.; Abedi, A. Coordination number in copper(II) complexes with bipyridine-dicarboxylate anion and diamine derivatives. Res. Chem. Intermed. 2018, 44, 7411-7426.
https://doi.org/10.1007/s11164-018-3563-1

[25]. Merabet, L.; Setifi, Z.; Ferjani, H.; Geiger, D. K.; Glidewell, C.; Kanmazalp, S. D.; Setifi, F.; Kaboub, L. Dinuclear azide-bridged copper(II) polymer with azido···π(pyridiyl) interaction: Synthesis, crystal structure and Hirshfeld surface analysis. J. Chem. Crystallogr. 2022, https://doi.org/10.1007/s10870-022-00960-2.
https://doi.org/10.1007/s10870-022-00960-2

[26]. Yousefi, M.; Khalighi, A.; Tadayon Pour, N.; Amani, V.; Khavasi, H. R. Diaqua(2,2′-bipyridine-5,5′-dicarboxylato-κ2N,N′)(ethylenediamine-κ2N,N′)copper(II) 2.5-hydrate. Acta Crystallogr. Sect. E Struct. Rep. Online 2008, 64, m1284-m1285.
https://doi.org/10.1107/S1600536808029061

[27]. Strotmeyer, K. P.; Fritsky, I. O.; Ott, R.; Pritzkow, H.; Krämer, R. Evaluating the conformational role of an allosteric CuII ion in anion recognition and catalysis by a tricopper complex. Supramol. Chem. 2003, 15, 529-547.
https://doi.org/10.1080/10610270310001605124

[28]. Iskenderov, T. S.; Golenya, I. A.; Gumienna-Kontecka, E.; Fritsky, I. O.; Prisyazhnaya, E. V. (2RS)-3-Hydr-oxy-2-methyl-2-(2-pyrid-yl) imidazolidine-4-one. Acta Crystallogr. Sect. E Struct. Rep. Online 2009, 65, o2123-4.
https://doi.org/10.1107/S1600536809030840

[29]. Golenya, I. A.; Gumienna-Kontecka, E.; Boyko, A. N.; Haukka, M.; Fritsky, I. O. Collapsed Cu(II)-hydroxamate metallacrowns. Inorg. Chem. 2012, 51, 6221-6227.
https://doi.org/10.1021/ic300387e

[30]. Qadir, A. M.; Kansiz, S.; Rosair, G. M.; Dege, N.; Safyanova, I. S. Crystal structure and Hirshfeld surface analysis of a zinc xanthate complex containing the 2,2'-bi-pyridine ligand. Acta Crystallogr. E Crystallogr. Commun. 2019, 75, 1857-1860.
https://doi.org/10.1107/S2056989019014968

[31]. Saeed, A.; Rafique, H.; Flörke, U. Methyl 4-methyl-benzoate. Acta Crystallogr. Sect. E Struct. Rep. Online 2008, 64, o821.
https://doi.org/10.1107/S1600536808008738

[32]. Demir, S.; Cakmak, S.; Dege, N.; Kutuk, H.; Odabasoglu, M.; Kepekci, R. A. A novel 3-acetoxy-2-methyl-N-(4-methoxyphenyl)benzamide: Molecular structural describe, antioxidant activity with use X-ray diffractions and DFT calculations. J. Mol. Struct. 2015, 1100, 582-591.
https://doi.org/10.1016/j.molstruc.2015.08.014

Supporting Agencies

The Scientific and Technological. Research Application and Research Center, Sinop University, Sinop, Turkey.
Most read articles by the same author(s)

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).