Home Crystal structure of [6,6′-((1E,1′E)-(propane-1,3- diylbis(azaneylylidene))bis(methaneylylidene)) bis(3-chlorophenol)-κ4N,N′,O,O′] copper(II), C17H14Cl2CuN2O2
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Crystal structure of [6,6′-((1E,1′E)-(propane-1,3- diylbis(azaneylylidene))bis(methaneylylidene)) bis(3-chlorophenol)-κ4N,N′,O,O′] copper(II), C17H14Cl2CuN2O2

  • Baiying Wei ORCID logo and Chenzhong Cao EMAIL logo
Published/Copyright: August 3, 2021

Abstract

C17H14Cl2CuN2O2, monoclinic, C2/c (no. 15), a = 22.743(4) Å, b = 8.0434(15) Å, c = 8.9388(17) Å, V = 1630.8(5) Å3, Z = 4, R gt (F) = 0.0376, wRref(F2) = 0.0997, T = 296(2) K.

CCDC no.: 2090336

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.

Table 1:

Data collection and handling.

Crystal: Black block
Size: 0.22 × 0.18 × 0.14 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.68 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θmax, completeness: 25.0°, >99%
N(hkl)measured, N(hkl)unique, Rint: 4151, 1449, 0.023
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1154
N(param)refined: 123
Programs: Bruker [1], SHELX [2], Olex2 [3]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z Uiso*/Ueq
Cu1 0.500000 0.46495 (6) 0.750000 0.0615 (2)
Cl1 0.28741 (5) −0.06158 (17) 0.44459 (13) 0.1018 (4)
O1 0.44328 (10) 0.2942 (3) 0.7093 (3) 0.0628 (6)
N1 0.45644 (15) 0.6245 (3) 0.6191 (4) 0.0748 (9)
C1 0.40053 (13) 0.2882 (4) 0.6034 (4) 0.0580 (8)
C2 0.36714 (13) 0.1414 (5) 0.5848 (4) 0.0629 (9)
H2 0.373861 0.053845 0.651793 0.075*
C3 0.32476 (14) 0.1267 (6) 0.4684 (4) 0.0737 (10)
C4 0.31140 (18) 0.2532 (7) 0.3696 (5) 0.0928 (13)
H4 0.283212 0.239169 0.289861 0.111*
C5 0.34051 (19) 0.4007 (7) 0.3910 (4) 0.0899 (13)
H5 0.330381 0.488990 0.327046 0.108*
C6 0.38572 (15) 0.4242 (5) 0.5072 (4) 0.0668 (9)
C7 0.41233 (19) 0.5829 (5) 0.5270 (5) 0.0768 (10)
H7 0.396109 0.667446 0.466207 0.092*
C8a 0.4630 (11) 0.8084 (12) 0.618 (3) 0.125 (9)
H8Aa 0.427850 0.859470 0.652911 0.150*
H8Ba 0.467233 0.846092 0.516234 0.150*
C9a 0.5166 (5) 0.8622 (9) 0.7182 (16) 0.100 (4)
H9Aa 0.551721 0.827456 0.671390 0.120*
H9Ba 0.517028 0.982707 0.722659 0.120*
C10a 0.5200 (10) 0.7979 (13) 0.872 (2) 0.103 (9)
H10Aa 0.481044 0.799724 0.909843 0.123*
H10Ba 0.545369 0.869600 0.936092 0.123*
  1. aOccupancy: 0.5.

Source of material

The title salen-type Schiff base ligand was prepared according to the literature method [4, 5] and the title complex was prepared according to the literature reported earlier [6]. The ethanol solution (20 ml) of the copper(II) acetate monohydrate (2 mmol) was slowly added into the ethanol solution (10 ml) of the title Schiff base ligand (2 mmol). The resulting mixture was kept being stirred for 1 h at room temperature until precipitation occurs. The product was collected by filtration and washed with ethanol solution. Then the product was dissolved in anhydrous ethanol and allowed to stand at room temperature 30 days in a quiet environment. Several block crystals were obtained.

Experimental details

H atoms were geometrically added and isotropically refined by the riding model. The propan-diyl moiety is disordered (see the Figure).

Comment

Some salen-type Schiff base complexes show photophysical properties, extensive attention has been attracted and were applied to many fields [7, 8]. And copper salen-type Schiff base complexes are amongst the most versatile catalysts known for oxygenation reactions [9]. So, a variety of salen-type complexes have been synthesized and investigated [10], [11], [12], [13].

In the crystal structure of the title compound the Cu atom is four-coordinated by two O atoms and two N atoms of the corresponding salen-type Schiff base ligand forming a tetrahedral N2O2 coordination mode. The bond lengths of Cu1–O1 is 1.901(2) Å and the Cu1–N1 is 1.957(3) Å. The angles of N1–Cu1–O1, N1–Cu1–N1′, O1–N1–O1′ and N1–Cu1–O1′ are 93.00(2), 98.0(2), 87.50(13) and 153.53(11)°, respectively.


Corresponding author: Chenzhong Cao, School of Resource Environment and Safety Engineering, School of Chemistry and Chemical Engineering, Key Laboratory of Theoretical Organic Chemistry and Function Molecule, Ministry of Education, Hunan University of Science and Technology, Xiangtan, 411201, P. R. China, E-mail:

Award Identifier / Grant number: 21672058

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: The work was supported by the National Natural Science Foundation of China (21672058).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Bruker. APEX2, Saint and SADABS; Bruker AXS Inc.: Madison, WI, USA, 2012.Search in Google Scholar

2. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Search in Google Scholar

3. 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

4. Shi, L., Ge, H., Tan, S., Li, H., Song, Y., Zhu, H., Tan, R. Synthesis and antimicrobial activities of Schiff bases derived from 5-chloro- salicylaldehyde. Eur. J. Med. Chem. 2007, 42, 558–564; https://doi.org/10.1016/j.ejmech.2006.11.010.Search in Google Scholar

5. Asadi, Z., Shorkaei, M. R. Synthesis, X-ray crystallography, thermal studies, spectroscopic and electrochemistry investigations of uranyl Schiff base complexes. Spectrochim. Acta, Part A 2013, 105, 344–351; https://doi.org/10.1016/j.saa.2012.12.024.Search in Google Scholar

6. Kargar, H., Ardakani, A. A., Tahir, M. N., Ashfaq, M., Munawar, K. S. Synthesis, spectral characterization, crystal structure and antibacterial activity of nickel(II), copper(II) and zinc(II) complexes containing ONNO donor Schiff base ligands. J. Mol. Struct. 2021, 1233, 130112; https://doi.org/10.1016/j.molstruc.2021.130112.Search in Google Scholar

7. Andruh, M. Compartmental Schiff-base ligands–a rich library of tectons in designing magnetic and luminescent materials. Chem. Commun. 2011, 47, 3025–3042; https://doi.org/10.1039/c0cc04506c.Search in Google Scholar

8. Chen, L., Ding, L., Chu, Z., Yong, L., Lü, X., Song, J., Fan, D., Jin, W. Bulk solvent-free melt ring-opening polymerization of L -lactide catalyzed by Cu(II) and Cu(II)—Nd(III) complexes of the Salen-type Schiff-base ligand. J. Appl. Organomet. Chem. 2011, 25, 310–316; https://doi.org/10.1002/aoc.1760.Search in Google Scholar

9. Rayati, S., Zakavi, S., Koliaei, M., Kozakiewicz, A. Electron-rich salen-type Schiff base complexes of Cu(II) as catalysts for oxidation of cyclooctene and styrene with tert-butylhydroperoxide: a comparison with electron-deficient ones. Inorg. Chem. Commun. 2010, 13, 203–207; https://doi.org/10.1016/j.inoche.2009.11.016.Search in Google Scholar

10. Nathan, L. C., Koehne, J. E., Gilmore, J. M., Hannibal, K. A., Dewhirst, W. E., Mai, T. D. The X-ray structures of a series of copper(II) complexes with tetradentate Schiff base ligands derived from salicylaldehyde and polymethylenediamines of varying chain length. Polyhedron 2003, 22, 887–894; https://doi.org/10.1016/s0277-5387(03)00029-9.Search in Google Scholar

11. You, Z. L., Lu, Y., Zhang, N., Ding, B. W., Sun, H., Hou, P., Wang, C. Preparation and structural characterization of hetero-dinuclear Schiff base copper(II)-zinc(II) complexes and their inhibition studies on Helicobacter pylori urease. Polyhedron 2011, 30, 2186–2194; https://doi.org/10.1016/j.poly.2011.05.048.Search in Google Scholar

12. Tella, S., Bekiari, V., Kessler, V. G., Papaefstathiou, G. S. Gallium(III) complexes based on N,N′-bis(salicylidene)propane-1,3-diamine and its derivatives. Polyhedron 2013, 64, 77–83; https://doi.org/10.1016/j.poly.2013.02.057.Search in Google Scholar

13. Xiao, J. C., Zhou, C., Huang, M. F., Tan, H., Wu, Q. Crystal structure of aqua-azido-κ1N-(6,6′-((propane-1,3-diylbis(azanylylidene)) bis(methanylylidene)) bis(3-bromophenolato)- κ4N,N′,O,O′iron(III), C17H16Br2FeN5O3. Z. Kristallogr. NCS 2020, 235, 903–904; https://doi.org/10.1515/ncrs-2020-0091.Search in Google Scholar

Received: 2021-06-18
Accepted: 2021-07-20
Published Online: 2021-08-03
Published in Print: 2021-12-20

© 2021 Baiying Wei and Chenzhong Cao, published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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