Abstract
C34H34CuN4O6, Monoclinic, P21/c, a = 10.4018(4) Å, b = 6.1634(2) Å, c = 24.2227(15) Å, β = 101.820(5)°, Z = 2, V = 1520.01(13) Å3, Rgt(F) = 0.0565, wRref(F2) = 0.1455, T = 292 K.
The crystal title structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.
Crystal: | Clear light red block |
Size: | 0.24 × 0.21 × 0.16 mm |
Wavelength: | Mo Kα radiation (0.71073 Å) |
μ: | 0.77 mm−1 |
Diffractometer, scan mode: | SuperNova, ω |
θmax, completeness: | 26.0°, 99.7% |
N(hkl)measured, N(hkl)unique, Rint: | 5769, 2976, 0.039 |
Criterion for Iobs, N(hkl)gt: | Iobs > 2 σ(Iobs), 2206 |
N(param)refined: | 208 |
Programs: | Olex2 [25], CrysAlis PRO [26], SHEL [24] |
Atom | x | y | z | Uiso*/Ueq |
---|---|---|---|---|
Cu1 | 1.0000 | 0.0000 | 0.5000 | 0.0247(2) |
O1 | 0.3629(3) | 0.3197(5) | 0.65238(12) | 0.0356(7) |
O2 | 1.0320(3) | −0.0707(4) | 0.42829(11) | 0.0312(7) |
O3 | 1.2118(3) | 0.1246(5) | 0.27022(11) | 0.0325(7) |
N1 | 0.4417(3) | 0.2707(6) | 0.61350(14) | 0.0311(8) |
N2 | 0.8768(3) | 0.2317(5) | 0.46522(12) | 0.0236(7) |
C1 | 0.7781(3) | 0.2979(6) | 0.49570(15) | 0.0221(8) |
C2 | 0.6921(4) | 0.1419(6) | 0.50698(17) | 0.0283(9) |
H2 | 0.6928 | 0.0043 | 0.4913 | 0.034* |
C3 | 0.6056(4) | 0.1880(7) | 0.54112(17) | 0.0289(9) |
H3 | 0.5483 | 0.0807 | 0.5483 | 0.035* |
C4 | 0.6018(3) | 0.3928(6) | 0.56541(15) | 0.0228(8) |
C5 | 0.6863(3) | 0.5500(6) | 0.55223(16) | 0.0267(9) |
H5 | 0.6846 | 0.6888 | 0.5671 | 0.032* |
C6 | 0.7731(3) | 0.5045(6) | 0.51729(16) | 0.0252(8) |
H6 | 0.8278 | 0.6127 | 0.5084 | 0.030* |
C7 | 0.5134(3) | 0.4341(7) | 0.60514(16) | 0.0253(9) |
C8 | 0.5133(4) | 0.6493(7) | 0.6334(2) | 0.0437(12) |
H8A | 0.4864 | 0.7596 | 0.6054 | 0.066* |
H8B | 0.6001 | 0.6811 | 0.6542 | 0.066* |
H8C | 0.4533 | 0.6457 | 0.6586 | 0.066* |
C9 | 0.2949(5) | 0.1265(8) | 0.6611(2) | 0.0492(13) |
H9A | 0.2519 | 0.0682 | 0.6253 | 0.074* |
H9B | 0.2307 | 0.1588 | 0.6833 | 0.074* |
H9C | 0.3563 | 0.0221 | 0.6806 | 0.074* |
C10 | 0.8904(3) | 0.3362(6) | 0.42059(15) | 0.0245(8) |
H10 | 0.8403 | 0.4609 | 0.4113 | 0.029* |
C11 | 0.9770(3) | 0.2742(6) | 0.38423(15) | 0.0228(8) |
C12 | 0.9939(4) | 0.4171(7) | 0.34096(16) | 0.0296(9) |
H12 | 0.9513 | 0.5506 | 0.3376 | 0.036* |
C13 | 1.0715(4) | 0.3637(7) | 0.30390(16) | 0.0315(9) |
H13 | 1.0825 | 0.4603 | 0.2757 | 0.038* |
C14 | 1.1347(3) | 0.1607(7) | 0.30881(15) | 0.0267(9) |
C15 | 1.1186(4) | 0.0163(6) | 0.34978(15) | 0.0252(8) |
H15 | 1.1590 | −0.1188 | 0.3516 | 0.030* |
C16 | 1.0413(3) | 0.0708(6) | 0.38914(15) | 0.0235(8) |
C17 | 1.2808(4) | −0.0752(8) | 0.27302(19) | 0.0411(11) |
H17A | 1.3351 | −0.0757 | 0.2454 | 0.062* |
H17B | 1.2191 | −0.1928 | 0.2656 | 0.062* |
H17C | 1.3349 | −0.0923 | 0.3100 | 0.062* |
Source of material
All reagents and starting materials were obtained from commercial suppliers and used as received. Synthesis of the ligand was prepared by a similar method reported earlier [1], [2], [3], [4], [5]. A solution of copper(II) acetate monohydrate (2.0 mg, 10 mmol) in ethanol (2 mL) was added dropwise to a solution of ligand (E)-1-(4-(((E)-2-hydroxy-4-methoxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime (6.0 mg, 20 mmol) in ethanol (5 mL) at room temperature. Immediately, the color of the solution turned brown, and the solution was stirred for 1 h. The solution was filtered and the filtrate was allowed to stand at room temperature for about six weeks, and we got several clear light red block crystals. Elemental analysis: Anal. calcd for C34H34CuN4O6: C, 62.04%; H, 5.21%; N, 8.51%; Found: C, 62.09%; H, 5.20%; N, 8.46%.
Experimental details
Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.
Discussion
Oxime-type compounds, a unique family of organic compounds with a wide spectrum of practical applications, can act as chelating agents with various metal ions [6], [7], [8], [9], [10], [11]. Owing to their unique chemical reactivity, oxime derivatives have found their ways into a wide range of industrial practices and engineering applications, including photophysical properties [12], [13], [14], [15], [16], molecular recognition [17, 18] and supramolecular architectures [19], [20], [21], [22], [23] and so on.
We have designed and synthesized a new copper(II) complex, which is built up by the C34H34CuN4O6 complexes. Cu1 is four-coordinated by two O atoms and two N atoms from two different ligands. The Cu1–N2 bond lengths are both 1.987(3) Å and the Cu1–O2 bond lengths are both 1.885(3) Å . The angles of N2–Cu1–O2 and N2–Cu1–O2i are 89.76(12) and 90.25(12), respectively. All geometric parameters are in the typical ranges.
References
Zhao, L.; Zhao, J. X.; An, Q. Q.; Wang, F.: Crystal structure of (E)-1-(4-(((E)-3,5-dibromo-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime C17H16Br2N2O2. Z. Kristallogr. NCS 231 (2016) 1053–1054.10.1515/ncrs-2016-0047Search in Google Scholar
Yang, Y. H.; Wu, J. C.; Gong, S. S.; Wang, J. S.: 4-Bromo-2-({4-[(hydroxyimino)methyl]phenyl}imino-methyl)phenol. Acta Crystallogr. E66 (2010) o2014.10.1107/S160053681002698XSearch in Google Scholar PubMed PubMed Central
Zhao, L.; Wang, F.; An, Q. Q.; Zhao, J. X.: Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-ethyl oxime, C17H16Cl2N2O2. Z. Kristallogr. NCS 231 (2016) 1045–1046.10.1515/ncrs-2016-0044Search in Google Scholar
Zhao, L.; Dong, X. T.; Wang, L.; Cheng, Q.; Zhao, J. X.: Synthesis and crystal structure of 1-(4-{[(E)-3,5-dibromo-2-hydroxybenzylidene]amino}phenyl) ethanone oxime. Asian J. Chem. 25 (2013) 4061–4063.10.14233/ajchem.2013.14022Search in Google Scholar
Zhao, L.; Yan, X. L.; Wang, P.; Cheng, Q.; Guo, H. X.: Synthesis, characterization and crystal structure of 1-(4-{[(E)-4-methoxyl-2-hydroxybenzylidene]amino} henyl)ethanone oxime and its copper(II) complex. Asian J. Chem. 26 (2014) 8098–8100.10.14233/ajchem.2014.17378Search in Google Scholar
Lacroix, P. G.; Averseng, F.; Malfant, I.; Nakatani, K.: Synthesis, crystal structures, and molecular hyperpolarizabilities of a new Schiff base ligand, and its copper(II), nickel(II), and cobalt(II) metal complexes. Inorg. Chim. Acta 357 (2004) 3825–3835.10.1016/j.ica.2004.03.004Search in Google Scholar
Han, Q. F.; Jian, F. F.; Lu, L. D.; Yang, X. J.; Wang, X.: Structure and characterization of bis(N-p-chloro-phenyl-salicylideneaminate) Schiff base copper(II) complex: Cu[N-p-Cl-Ph-Sal]2. J. Chem. Cryst. 31 (2001) 247–250.10.1023/A:1014366326391Search in Google Scholar
Kamenar, B.; Stefanovic, A.; Antolic, S.: Redetermination of the crystal structure of bis(N-phenylsalicylideneaminato)copper(II), Cu(C13H10NO)2. Z. Kristallogr. NCS 210 (1995) 730–730.10.1524/zkri.1995.210.9.730Search in Google Scholar
Dong, W. K.; Zhang, J. T.; Dong, Y. J.; Zhang, Y.; Wang, Z. K.: Construction of mononuclear copper(II) and trinuclear cobalt(II) complexes based on asymmetric Salamo-type ligands. Z. Anorg. Allg. Chem. 642 (2016) 189–196.10.1002/zaac.201500751Search in Google Scholar
Burgess, J.; Fawcett, J.; Palma, V.; Gilani, S. R.: Fluoro derivatives of bis(salicylideneaminato-N,O) copper(II) and -oxovanadium(IV). Acta Crystallogr. C57 (2001) 277–280.10.1107/S0108270100020059Search in Google Scholar PubMed
Cseh, L.; Pantenburg, I.; Meyer, G.; Costisor, O.: Structures and spectral properties of a copper(II) complex with N-salicylidene-p-toluidine. Rev. Roumaine Chim. 49 (2004) 287–291.Search in Google Scholar
Dong, W. K.; Duan, J. G.; Guan, Y. H.; Shi, J. Y.; Zhao, C. Y.: Synthesis, crystal structure and spectroscopic behaviors of Co(II) and Cu(II) complexes with Salen-type bisoxime ligands. Inorg. Chim. Acta 362 (2009) 1129–1134.10.1016/j.ica.2008.05.028Search in Google Scholar
Dong, W. K.; Gong, S. S.; Tong, J. F.; Sun, Y. X.; Wu, J. C.: Syntheses and structure of two copper(II) complexes with salicyl mono-oxime ligands. Chinese J. Inorg. Chem. 26 (2010) 1868–1874.Search in Google Scholar
Dong, W. K.; Zhu, L. C.; Dong, Y. J.; Ma, J. C.; Zhang, Y.: Mono, di and heptanuclear metal(II) complexes based on symmetric and asymmetric tetradentate Salamo-type ligands: Syntheses, structures and spectroscopic properties. Polyhedron 117 (2016) 148–154.10.1016/j.poly.2016.05.055Search in Google Scholar
Sun, Y. X.; Li, C. Y.; Yang, C. J.; Zhao, Y. Y.; Guo, J. Q.; Yu, B.: Two Cu(II) complexes with Schiff base ligands: syntheses, crystal structure, spectroscopic roperties, and substituent effect. Chin. J. Inorg. Chem. 32 (2016) 327–335.Search in Google Scholar
Dong, W. K.; Ma, J. C.; Zhu, L. C.; Sun, Y. X.; Sunday, F. A.; Zhang, Y.: A series of heteromultinuclear zinc(II)-lanthanide(III) complexes based on 3-MeOsalamo: syntheses, structural characterizations, and luminescent properties. Cryst. Growth Des. 16 (2016) 6903–6914.10.1021/acs.cgd.6b01067Search in Google Scholar
Dong, W. K.; Li, X. L.; Wang, L.; Zhang, Y.; Ding, Y. J.: A new application of Salamo-type bisoximes: as a relay-sensor for Zn2+/Cu2+ and its novel complexes for successive sensing of H+/OH−. Sens. Actuators B 229 (2016) 370–378.10.1016/j.snb.2016.01.139Search in Google Scholar
Dong, W. K.; Sunday, F. A.; Zhang, Y.; Sun, Y. X.; Dong, X. Y.: A reversible ”turn-on” fluorescent sensor for selective detection of Zn2+. Sens. Actuators B 238 (2017) 723–734.10.1016/j.snb.2016.07.047Search in Google Scholar
Sun, Y. X.; Lu, R. E.; Li, X. R.; Zhao, Y. Y.; Li, C. Y.: A Schiff base ligand containing oxime group and its Cu(II) complex: Syntheses and supramolecular structures. Chin. J. Inorg. Chem. 31 (2015) 1055–1062.Search in Google Scholar
Dong, W. K.; Sun, Y. X.; Zhang, Y. P.; Li, L.; He, X. N.; Tang, X. L.: Synthesis, crystal structure, and properties of supramolecular Cu(II), Zn(II), and Cd(II) complexes with Salen-type bisoxime ligands. Inorg. Chim. Acta 362 (2009) 117–124.10.1016/j.ica.2008.03.128Search in Google Scholar
Zhao, L.; Dong, X. T.; Sun, Y. X.; Cheng, Q.; Dong, X. Y.; Wang, L.: Synthesis, crystal structure and thermal property of a 1D chain-like copper(II) complex. Chinese J. Inorg. Chem. 28 (2012) 2413–2418.Search in Google Scholar
Sun, Y. X.; Xu, L.; Zhao, T. H.; Liu, S. H.; Liu, G. H.; Dong, X. T.: Synthesis and crystal structure of a 3D supramolecular copper(II) complex with 1-(3-phenyl)ethanone oxime. Synth. React. Inorg. Metal-Org. Nano-Met. Chem. 43 (2013) 509–513.10.1080/15533174.2012.740756Search in Google Scholar
Sun, Y. X.; Zhao, Y. Y.; Li, C. Y.; Yu, B.; Guo, J. Q.; Li, J.: Supramolecular cobalt(II) and copper(II) complexes with Schiff base ligand: syntheses, characterizations and crystal structures. Chin. J. Inorg. Chem. 32 (2016) 913–920.Search in Google Scholar
Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed
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. 42 (2009) 339–341.10.1107/S0021889808042726Search in Google Scholar
CrysAlis PRO: Oxford Diffraction/Agilent Technologies UK Ltd, Yarnton, England.Search in Google Scholar
©2017 Ji-Xing Zhao, et al., published by De Gruyter, Berlin/Boston
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.