Crystal structure of bis{2-(((4-(1-(hydroxyl-imino)ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C30H26CoN4O4

Yi Jin; Tao Fu; Bo-Yang Ma; Ping Wei; Ji-Xing Zhao; Li Zhao

doi:10.1515/ncrs-2020-0189

Open Access Published by De Gruyter (O) May 22, 2020

Crystal structure of bis{2-(((4-(1-(hydroxyl-imino)ethyl)phenyl)imino)methyl)phenolato-κ²N,O}cobalt(II), C₃₀H₂₆CoN₄O₄

Yi Jin , Tao Fu , Bo-Yang Ma , Ping Wei , Ji-Xing Zhao and Li Zhao

From the journal Zeitschrift für Kristallographie - New Crystal Structures

https://doi.org/10.1515/ncrs-2020-0189

Abstract

C₃₀H₂₆CoN₄O₄, monoclinic, C2/c (no. 15), a = 16.0520(5) Å, b = 19.1890(5) Å, c = 16.7292(4) Å, β = 93.064(1)°, Z = 8, V = 5145.6(2) Å³, R_gt(F) = 0.0400, wR_ref(F²) = 0.0932, T = 173(2) K.

CCDC no.: 2003147

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:	Red block
Size:	0.19 × 0.17 × 0.14 mm
Wavelength:	Mo Kα radiation (0.71073 Å)
μ:	0.71 mm⁻¹
Diffractometer, scan mode:	Bruker D8 Venture, φ and ω
θ_max, completeness:	25.4°, >99%
N(hkl)_measured, N(hkl)_unique, R_int:	27339, 4709, 0.045
Criterion for I_obs, N(hkl)_gt:	I_obs > 2 σ(I_obs), 3751
N(param)_refined:	358
Programs:	Bruker [1], SHELX [2]

Table 2:

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

Atom	x	y	z	U_iso*/U_eq
Co1	0.74731(2)	0.43934(2)	0.37733(2)	0.02373(11)
O1	0.82360(11)	0.48662(9)	0.45013(10)	0.0286(4)
N1	0.69604(12)	0.38128(10)	0.45953(12)	0.0237(4)
C1	0.83809(15)	0.47118(13)	0.52682(15)	0.0263(5)
N2	0.41722(13)	0.14739(12)	0.40231(13)	0.0338(5)
O2	0.34500(12)	0.11064(11)	0.37963(12)	0.0447(5)
H2A	0.3426(11)	0.0684(18)	0.4111(18)	0.067*
C2	0.90436(18)	0.50524(14)	0.56937(17)	0.0350(7)
H2	0.937538	0.537733	0.542337	0.042*
O3	0.67156(11)	0.48823(9)	0.30517(10)	0.0297(4)
N3	0.79967(12)	0.38342(10)	0.29381(12)	0.0253(5)
C3	0.92185(19)	0.49228(16)	0.64930(18)	0.0427(8)
H3	0.967406	0.515582	0.676229	0.051*
N4	1.07329(14)	0.14491(12)	0.35527(13)	0.0358(5)
O4	1.14596(13)	0.10895(11)	0.37776(12)	0.0467(5)
H4A	1.1487(11)	0.0666(19)	0.3468(19)	0.070*
C4	0.87437(18)	0.44583(16)	0.69170(17)	0.0407(7)
H4	0.886542	0.437708	0.747111	0.049*
C5	0.80956(17)	0.41208(14)	0.65142(16)	0.0336(6)
H5	0.776474	0.380674	0.680085	0.040*
C6	0.79016(15)	0.42230(13)	0.56881(15)	0.0261(5)
C7	0.72269(15)	0.38164(12)	0.53407(15)	0.0261(5)
H7	0.694614	0.351927	0.569231	0.031*
C8	0.62912(15)	0.33508(13)	0.43514(14)	0.0252(5)
C9	0.62881(15)	0.26510(13)	0.45680(15)	0.0288(6)
H9	0.673686	0.246452	0.489409	0.035*
C11	0.49572(15)	0.24892(13)	0.38429(15)	0.0253(5)
C10	0.56331(15)	0.22277(13)	0.43094(15)	0.0291(6)
H10	0.564249	0.174841	0.445179	0.035*
C12	0.49805(16)	0.31873(13)	0.36151(16)	0.0299(6)
H12	0.453237	0.337502	0.328924	0.036*
C13	0.56450(16)	0.36123(13)	0.38553(16)	0.0300(6)
H13	0.565820	0.408299	0.368023	0.036*
C14	0.42261(16)	0.20464(13)	0.36227(15)	0.0278(6)
C15	0.35862(18)	0.22933(16)	0.30051(18)	0.0426(7)
H15A	0.383966	0.233235	0.248685	0.064*
H15B	0.337534	0.274997	0.316140	0.064*
H15C	0.312400	0.195941	0.296192	0.064*
C16	0.66026(15)	0.47724(13)	0.22702(15)	0.0260(5)
C17	0.59728(17)	0.51499(14)	0.18439(17)	0.0328(6)
H17	0.564443	0.547141	0.212276	0.039*
C18	0.58212(18)	0.50647(15)	0.10338(18)	0.0379(7)
H18	0.539406	0.532960	0.076151	0.045*
C19	0.62876(18)	0.45935(15)	0.06070(17)	0.0382(7)
H19	0.617721	0.453252	0.004779	0.046*
C20	0.69052(17)	0.42210(14)	0.10042(16)	0.0332(6)
H20	0.722803	0.390607	0.071048	0.040*
C21	0.70810(15)	0.42884(13)	0.18410(15)	0.0271(5)
C22	0.77454(16)	0.38646(13)	0.21899(15)	0.0275(6)
H22	0.803045	0.357581	0.183279	0.033*
C23	0.86621(15)	0.33682(13)	0.31798(14)	0.0261(5)
C24	0.86606(16)	0.26708(13)	0.29573(15)	0.0296(6)
H24	0.820763	0.248770	0.263397	0.035*
C25	0.93149(16)	0.22441(13)	0.32047(15)	0.0304(6)
H25	0.930426	0.176725	0.305201	0.036*
C26	0.99954(16)	0.24982(13)	0.36763(15)	0.0274(5)
C27	0.99701(16)	0.31923(14)	0.39149(16)	0.0329(6)
H27	1.041568	0.337521	0.424792	0.039*
C28	0.93112(16)	0.36212(13)	0.36779(17)	0.0323(6)
H28	0.930272	0.409091	0.385675	0.039*
C29	1.07295(16)	0.20528(13)	0.38951(15)	0.0286(6)
C30	1.14302(18)	0.23117(16)	0.44496(17)	0.0414(7)
H30A	1.196566	0.218239	0.423624	0.062*
H30B	1.138546	0.210138	0.497941	0.062*
H30C	1.139629	0.281996	0.449455	0.062*

Source of material

Synthesis of the title complex was prepared by a similar method reported earlier [3], [4] and the ligand was prepared according to the literature reported earlier [5]. A solution of cobalt acetate tetrahydrate (249.08 mg, 1 mmol) in MeOH (2 mL) was added to a stirring solution of the educt 1-(4-((2-hydroxybenzylidene)amino)phenyl)ethan-1-one oxime (254.30 mg, 1 mmol) in CH₂Cl₂ (2 mL). The mixture was continuously stirred for 1 h at room temperature. The product was filtered and the filtrate was allowed to stand at room temperature 20 days in a quiet environment. Several clear light red block crystals were obtained. Anal. Calcd. for C₃₀H₂₆CoN₄O₄: C, 63.72%; H, 4.63%; N, 9.91%. Found: C, 63.56%; H, 4.81%; N, 9.33%.

Experimental details

Hydrogen atoms were placed in their geometrically idealized positions and constrained to ride on their parent atoms.

Comment

The transition metal complexes based on Schiff bases ligand have also attracted considerable attention in the past decade [6], [7]. Cobalt complexes show effective applications in various fields of scientific research [8], [9], For example, the cobalt complex based on Schiff base are widely utilized in magnetic [10], [11], luminescence materials [12], [13] and supramolecular constructing [13], [14] fields and so on.

The crystal structure of the title compound was determined by X-ray crystallography. Co1 is four–coordinated by two O atoms and two N atoms forming a N₂O₂ coordination mode. The bond lengths of Co1—O1 is 1.9096(17) Å and the Co1—O3 is 1.9128(18) Å. And the bond lengths of Co1—N1 is 1.983(2) Å and the Co1—N3 is 1.984(2) Å. On the other hand, the angles of N1—Co1—O1 is 95.76(8)° and O1—Co1—O3 is 122.27(7)°. Compared with other similar structures, all geometric parameters are in the typical ranges [3], [4].

References

1. Bruker. APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, WI, USA (2012).Search in Google Scholar

2. Sheldrick, G. M.: A short history of SHELX. Acta Crystallogr. A64 (2008) 112–122.10.1107/S0108767307043930Search in Google Scholar PubMed

3. Fu, T.; Ma, J. X.; Wei, P.; Li, Q. L.; Zhao, J. X.; Zhao, L.: Synthesis and crystal structure of bis{2-bromo-6-(((4-(1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato–κ²N,O}cobalt(II)–dichloromethane(1/1), C₃₄H₃₂Br₂Cl₄CoN₄O₄. Z. Kristallogr. NCS 235 (2020) 59–60.10.1515/ncrs-2019-0474Search in Google Scholar

4. Yang, Y. H.; Wei, Z. L.; Li, Y. Z.; Zhao, J. X.; Dong, W. K.: Synthesis and crystal structure of bis{2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato–κ²N,O}cobalt(II)–ethanol(1/1), C₃₄H₃₆CoN₄O₅. Z. Kristallogr. NCS 234 (2019) 379–381.10.1515/ncrs-2017-0413Search in Google Scholar

5. Li, P. P.; Zhao, L.; Liu, G. H.; Zhao, J. X.; Zhu, Z. B.: Synthesis and crystal structure of 1-{4-[(2-hydroxy-benzylidene)amino]phenyl}ethanone oxime, C₁₅H₁₄N₂O₂. Z. Kristallogr. NCS 232 (2017) 1005–1006.10.1515/ncrs-2017-0134Search in Google Scholar

6. Ma, J. X.; Li, Q. L.; Li, P. P.; Zhao, J. X.; Zhao, L.: Crystal structure of bis{5-methoxy-2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato–κ²N,O}nickel(II), C₃₄H₃₄N₄NiO₆. Z. Kristallogr. NCS 233 (2018) 767–769.10.1515/ncrs-2017-0379Search in Google Scholar

7. Li, Q. L.; Li, P. P.; Ma, J. X.; Zhao, J. X.; Zhao, L.: Crystal structure of bis{2-((E)-((4-((E)-1-(methoxyimino)ethyl)phenyl)imino)methyl)phenolato–κ²N,O}zinc(II), C₃₂H₃₀N₄O₄Zn. Z. Kristallogr. NCS 233 (2018) 637–639.10.1515/ncrs-2017-0404Search in Google Scholar

8. Zhang, H.; Dong, W. K.; Zhang, Y.; Akogun, S. F.: Naphthalenediol based bis(salamo)–type homo– and heterotrinuclear cobalt(II) complexes: syntheses, structures and magnetic properties. Polyhedron 133 (2017) 279–293.10.1016/j.poly.2017.05.051Search in Google Scholar

9. Jia, H. R.; Li, J.; Sun, Y. X.; Guo, J. Q.; Yu, B.; Wen, N.; Xu, L.: Two supramolecular cobalt(II) complexes: syntheses, crystal structures, spectroscopic behaviors, and counter anion effects. Crystals 7 (2017) 247–261.10.3390/cryst7080247Search in Google Scholar

10. Zheng, S. S.; Dong, W. K.; Zhang, Y.; Chen, L.; Ding, Y. J.: Four Salamo-type 3d–4f hetero-bimetallic [Zn^IILn^III] complexes: syntheses, crystal structures, and luminescent and magnetic properties. New J. Chem. 41 (2017) 4966–4973.10.1039/C6NJ04090JSearch in Google Scholar

11. Dong, W. K.; Ma, J. C.; Zhu, L. C.; Zhang, Y.: Nine self–assembled nickel(II)–lanthanide(III) heterometallic complexes constructed from a salamo–type bisoxime and bearing a N– or O–donor auxiliary ligand: syntheses, structures and magnetic properties. New J. Chem. 40 (2016) 6998–7010.10.1039/C6NJ00855KSearch in Google Scholar

12. Yu, B.; Sun, Y. X.; Yang, C. J.; Guo, J. Q.; Li, J.: Synthesis and crystal structures of an unexpected tetranuclear zinc(II) complex and a benzoquinone compound derived from Zn^II– and Cd^II– promoted reactivity of Schiff base ligands. Z. Anorg. Allg. Chem. 643 (2017) 689–698.10.1002/zaac.201700034Search in Google Scholar

13. 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

14. 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

Received: 2020-04-18

Accepted: 2020-05-11

Published Online: 2020-05-22

Published in Print: 2020-08-26

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