Home Crystal structure of azido-k1 N-{6,6′-((((methylazanediyl)bis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenolato)k5 N,N′,N″,O,O′}cobalt(III)-methanol (1/1)), C21H23Br4CoN6O3
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Crystal structure of azido-k1 N-{6,6′-((((methylazanediyl)bis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenolato)k5 N,N′,N″,O,O′}cobalt(III)-methanol (1/1)), C21H23Br4CoN6O3

  • Rui Duan , Hui Tian , Yu Guojun and Qiong Wu ORCID logo EMAIL logo
Published/Copyright: November 17, 2021

Abstract

C21H23Br4CoN6O3, monoclinic, P21/c (no. 14), a = 16.2300(4) Å, b = 20.9661(6) Å, c = 7.8269(2) Å, β = 97.2250(11)°, V = 2642.19(12) Å3, Z = 4, R gt (F) = 0.0336, wR ref (F 2) = 0.0981, T = 150.0 K.

CCDC no.: 2112998

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 × 0.20 × 0.18 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 6.73 mm−1
Diffractometer, scan mode: Xcalibur Eos, φ and ω
θ max, completeness: 26.4°, 99%
N(hkl)measured, N(hkl)unique, R int: 37,075, 5358, 0.045
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 4612
N(param)refined: 318
Programs: CrysAlisPRO [1], Olex2 [2], SHELX [3, 4]
Table 2:

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

Atom x y z U iso*/U eq
Br1 0.35748 (3) 0.70775 (2) −0.06633 (6) 0.04175 (12)
Br2 0.04508 (3) 0.71859 (2) −0.47685 (6) 0.05029 (13)
Br3 0.15392 (3) 0.31527 (2) 0.34082 (6) 0.04569 (13)
Br4 0.44511 (3) 0.20401 (3) 0.15173 (8) 0.06241 (16)
Co0A 0.25949 (3) 0.51921 (2) 0.19441 (6) 0.02955 (12)
O1 0.27174 (16) 0.60307 (13) 0.1100 (3) 0.0352 (6)
O2 0.24622 (16) 0.43650 (12) 0.2831 (3) 0.0338 (6)
N1 0.14114 (19) 0.53000 (15) 0.1745 (4) 0.0316 (7)
N2 0.2715 (2) 0.55001 (17) 0.4342 (4) 0.0385 (7)
H2 0.295521 0.512652 0.502650 0.046*
N3 0.37812 (19) 0.50775 (17) 0.2161 (4) 0.0348 (7)
N4 0.24707 (19) 0.48515 (16) −0.0407 (4) 0.0341 (7)
N5 0.3028 (2) 0.48924 (19) −0.1266 (4) 0.0426 (8)
N6 0.3556 (3) 0.4933 (3) −0.2144 (5) 0.0677 (13)
C1 0.1363 (2) 0.60913 (18) −0.0521 (5) 0.0328 (8)
C2 0.2207 (2) 0.62761 (18) −0.0143 (5) 0.0322 (8)
C3 0.2471 (2) 0.67741 (19) −0.1175 (5) 0.0349 (8)
C4 0.1962 (2) 0.70480 (19) −0.2525 (5) 0.0365 (8)
H4 0.216392 0.737577 −0.319905 0.044*
C5 0.1146 (3) 0.68336 (19) −0.2876 (5) 0.0361 (8)
C6 0.0844 (2) 0.63690 (19) −0.1874 (5) 0.0350 (8)
H6 0.028116 0.623734 −0.210636 0.042*
C7 0.0994 (2) 0.56606 (18) 0.0611 (5) 0.0325 (8)
H7 0.040537 0.564193 0.051346 0.039*
C8 0.0943 (2) 0.49533 (19) 0.2959 (5) 0.0355 (8)
H8A 0.096260 0.448933 0.273255 0.043*
H8B 0.035481 0.508991 0.279128 0.043*
C9 0.1325 (3) 0.5092 (2) 0.4826 (6) 0.0488 (11)
H9A 0.086820 0.518868 0.551364 0.059*
H9B 0.160327 0.469974 0.530908 0.059*
C10 0.1937 (3) 0.5628 (2) 0.5046 (6) 0.0487 (11)
H10A 0.167669 0.601304 0.447785 0.058*
H10B 0.206682 0.572366 0.628934 0.058*
C11 0.3343 (3) 0.6009 (3) 0.4743 (6) 0.0525 (11)
H11A 0.335212 0.613296 0.596492 0.063*
H11B 0.317119 0.638722 0.402972 0.063*
C12 0.4200 (3) 0.5826 (3) 0.4442 (6) 0.0541 (12)
H12A 0.438148 0.546369 0.520901 0.065*
H12B 0.457501 0.618895 0.478634 0.065*
C13 0.4309 (3) 0.5640 (2) 0.2608 (5) 0.0416 (9)
H13A 0.414041 0.599564 0.180935 0.050*
H13B 0.489826 0.553584 0.252583 0.050*
C14 0.4129 (2) 0.4536 (2) 0.2032 (5) 0.0378 (9)
H14 0.471080 0.453426 0.197924 0.045*
C15 0.3711 (2) 0.3925 (2) 0.1959 (5) 0.0382 (9)
C16 0.4164 (3) 0.3376 (2) 0.1652 (5) 0.0426 (9)
H16 0.470606 0.341411 0.132326 0.051*
C17 0.3825 (3) 0.2787 (2) 0.1826 (6) 0.0442 (10)
C18 0.3039 (3) 0.2717 (2) 0.2326 (6) 0.0440 (10)
H18 0.281083 0.230470 0.244834 0.053*
C19 0.2600 (2) 0.3253 (2) 0.2639 (5) 0.0384 (9)
C20 0.2900 (2) 0.38790 (19) 0.2461 (5) 0.0344 (8)
O3 0.09136 (19) 0.42434 (16) −0.1247 (5) 0.0555 (8)
H3 0.135219 0.445995 −0.110078 0.083*
C21 0.1106 (3) 0.3611 (2) −0.1612 (7) 0.0587 (13)
H21A 0.132326 0.359242 −0.272361 0.088*
H21B 0.060295 0.334921 −0.166228 0.088*
H21C 0.152491 0.344889 −0.070615 0.088*

Source of material

N′, N-bis(3-aminopropyl) methylamine (0.81 mL, 5 mmol) was added into an anhydrous ethanol solution (40 mL) of 3,5-bromosalicylaldehyde (1.90 g, 10 mmol). The solution was refluxed at 60 °C for ca. 3 h, the yellow suspension was then stirred at 60 °C for 30 min. Then, Co(NO3)2·6H2O (0.145 g, 0.5 mmol) was added and the resulting brown mixture was further stirred for another 30 min and filtered. The black crystals of the title compound were obtained after one week by slow evaporation.

Experimental details

The crystal sample was selected by microscope and mounted on a glass fiber. Structure solution and refinements were carried out using the Olex2 software package [2]. All the hydrogen atoms were theoretically placed onto the ligand and refined using the riding model approximation. For the –CH2-groups, C–H bonds length were fixed at 0.97 Å and for the aromatic C–H distances 0.93 Å was used.

Comment

Since the N atoms in –C=N– in Schiff bases have the advantages of a high affinity and coordination ability for different transition metal ions, Schiff base ligands can construct versatile functional complexes, and the design and synthesis of Schiff base complexes arouse great interest [5, 6]. Structures with corresponding halogenated ligands are still rare [7], [8], [9]. As a part of our current research the title complex was studied.

The Co(III) ion adopts a distorted octahedral geometry with a CoN4O2 core in the title compound. The environment around Co(III) comprises an azide ion and a nitrogen atom at the apical position and two nitrogen atoms and two oxygen atoms in the basal plane of which all the nitrogen and oxygen atoms (N1, N3, O1, O2) are from the pentadentate Schiff base ligand. Not surprisingly, the Co–N bond distances are longer than the Co–O bonds in the basal plane. The bond angles range from 87.34(13)° to 179.43(14)° in the title compound and are all in the expected ranges [10, 11].


Corresponding author: Qiong Wu, Department of Chemical Science and Technology, Kunming University, Kunming, Yunnan 65200, P. R. China, E-mail:

Funding source: Fund for Less Developed National Nature Science Foundation of China

Award Identifier / Grant number: 31760257

Award Identifier / Grant number: 21761017

Funding source: Yunnan Provincial Undergraduate Universities

Award Identifier / Grant number: 2017FH001-002

Funding source: Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province

Funding source: Recruitment Program of Yunnan Province Experts Provincial Young Talents

Award Identifier / Grant number: 2019HB098

Funding source: Ten-Thousand Talents Program of Yunnan Province

Award Identifier / Grant number: YNWR-QNBJ-2018-273

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

  2. Research funding: This work was supported by Fund for Less Developed National Nature Science Foundation of China (Nos. 31760257, 21761017) as well as the Joint Basic Research Program (partial) of Yunnan Provincial Undergraduate Universities (2017FH001-002), the Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province (IRTSTYN), the Recruitment Program of Yunnan Province Experts Provincial Young Talents (2019HB098) and the Ten-Thousand Talents Program of Yunnan Province (YNWR-QNBJ-2018-273).

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

References

1. Agilent Technologies. CrysAlisPRO Software system; Agilent Technologies UK Ltd: Oxford, UK, 2015.Search in Google Scholar

2. 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

3. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.Search in Google Scholar

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

5. Miyasaka, H., Saitoh, A., Abe, S. Magnetic assemblies based on Mn(III) salen analogues. Coord. Chem. Rev. 2007, 251, 2622–2664; https://doi.org/10.1016/j.ccr.2007.07.028.Search in Google Scholar

6. Kachi-Terajima, C., Ishii, R., Tojo, Y., Fukuda, M., Kitagawa, Y., Asaoka, M., Miyasaka, H. Ferromagnetic exchange coupling in a family of MnIII salen-type Schiff-base out-of-plane dimers. J. Phys. Chem. C 2017, 121, 12454–12468; https://doi.org/10.1021/acs.jpcc.7b03336.Search in Google Scholar

7. Ghosh, M., Mandal, S., Fleck, M., Saha, R., Rizzoli, C., Bandyopadhyay, D. Synthesis, crystal structure, and antimicrobial activity of a series of cobalt(III) Schiff base complexes. J. Coord. Chem. 2018, 71, 4180–4193; https://doi.org/10.1080/00958972.2018.1532080.Search in Google Scholar

8. Wu, Q., Tang, Y., Zi, Q. Synthesis, crystallographic structure, Hirshfeld surface analysis and DFT calculations of two salen-type halogenated Schiff- base Ni(II) complexes. Polyhedron 2019, 166, 123–129; https://doi.org/10.1016/j.poly.2019.03.021.Search in Google Scholar

9. Gomes, L., Pinho, D., Freire, C., de Castro, B. (1,4-Dioxane-O) {3,3′,5,5′-tetrachloro-2,2′-[4-methyl-4-azaheptane-1,7-diylbis(nitrilomethyl- idyne-N)]diphenolato-O,O′}nickel(II), [Ni(3,5-Cl4salMetrien)]. Acta Crystallogr. 1999, C55, 1425–1427; https://doi.org/10.1107/s0108270199004588.Search in Google Scholar

10. Mandal, S., Layek, M., Saha, R., Rizzoli, C., Bandyopadhyay, D. Synthesis, crystal structure and antibacterial activity of four mononuclear Schiff base complexes of copper(II) and nickel(II). Transition Met. Chem. 2021, 46, 9–16; https://doi.org/10.1007/s11243-020-00416-6.Search in Google Scholar

11. Li, T., Xu, X., Huang, M., Wang, M., Wu, Q. Crystal structure of tris(azido-κ1N)-(N-(2-aminoethyl)-N-methyl-1,3-propanediamine-κ3N,N′,N″)cobalt(III), C7H19CoN12. Z. Kristallogr. N. Cryst. Struct. 2021, 236, 357–358; https://doi.org/10.1515/ncrs-2020-0544.Search in Google Scholar

Received: 2021-09-29
Accepted: 2021-11-08
Published Online: 2021-11-17
Published in Print: 2022-02-23

© 2021 Rui Duan et al., published by De Gruyter, Berlin/Boston

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

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