Home Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
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Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9

  • Zhou Zhongyuan , Yang Liguo ORCID logo EMAIL logo , Zou Kun , Fu Jiaqi and Ji Xinyu
Published/Copyright: November 18, 2022

Abstract

C76H65N13Cl2Ni3O9, monoclinic, P21/n, a = 15.937(4) Å, b = 16.805(4) Å, c = 27.463(7) Å, β = 94.613(3)°, V = 7332(3) Å3, Z = 4, Rgt (F) = 0.0490, wRref (F 2) = 0.1596, T = 298 K.

CCDC no.: 2217920

The crystal 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: 0.17 × 0.12 × 0.08 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.90 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω-scans
θ max, completeness: 27.6°, >99%
N(hkl)measured, N(hkl)unique, R int: 78367, 16866, 0.041
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 11675
N(param)refined: 928
Programs: Bruker programs [1], Shelx [2, 3]
Table 2:

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

x y z U iso*/U eq
Ni1 0.57840 (2) 0.26476 (2) 0.38038 (2) 0.03263 (10)
Cl1 0.48043 (7) 0.31827 (11) 0.12749 (4) 0.1068 (5)
O1 0.76547 (18) 0.32019 (16) 0.48243 (9) 0.0661 (7)
N1 0.96745 (16) 0.34201 (16) 0.30767 (10) 0.0451 (6)
C1 0.1390 (2) 0.1977 (3) 0.41881 (16) 0.0776 (13)
H1 0.1611 0.2011 0.3885 0.093*
Ni2 0.83732 (2) 0.32671 (2) 0.31229 (2) 0.03728 (11)
Cl2 0.67252 (8) 0.26969 (9) 0.63572 (4) 0.0850 (4)
O2 0.84896 (12) 0.29712 (13) 0.38655 (7) 0.0428 (5)
N2 0.71812 (14) 0.30550 (14) 0.32390 (8) 0.0331 (5)
C2 0.0556 (3) 0.1781 (4) 0.4200 (2) 0.114 (2)
H2 0.0228 0.1673 0.3912 0.137*
Ni3 0.31677 (2) 0.23389 (2) 0.45099 (2) 0.04128 (11)
O3 0.80597 (13) 0.35326 (14) 0.24237 (7) 0.0461 (5)
N3 0.70463 (14) 0.28382 (14) 0.37274 (8) 0.0339 (5)
C3 0.0221 (3) 0.1747 (4) 0.4632 (2) 0.111 (2)
H3 −0.0344 0.1623 0.4648 0.133*
O4 0.57639 (12) 0.28586 (13) 0.30787 (7) 0.0392 (5)
N4 0.45166 (14) 0.25054 (13) 0.38845 (8) 0.0324 (5)
C4 0.0716 (3) 0.1894 (5) 0.5039 (2) 0.119 (2)
H4 0.0497 0.1877 0.5343 0.142*
O5 0.36931 (19) 0.32895 (15) 0.29200 (9) 0.0650 (7)
N5 0.43664 (15) 0.24795 (14) 0.43871 (8) 0.0343 (5)
C5 0.1562 (3) 0.2071 (4) 0.50020 (16) 0.0871 (15)
H5 0.1907 0.2159 0.5287 0.105*
O6 0.30644 (12) 0.23896 (13) 0.37511 (7) 0.0411 (5)
N6 0.82958 (17) 0.45276 (16) 0.33275 (9) 0.0457 (6)
C6 0.38798 (19) 0.1942 (2) 0.27219 (11) 0.0457 (7)
N7 0.56249 (16) 0.39070 (15) 0.39421 (9) 0.0426 (6)
O7 0.34524 (15) 0.23180 (16) 0.52280 (8) 0.0568 (6)
C7 0.3755 (3) 0.2069 (3) 0.22198 (13) 0.0672 (10)
H7 0.3625 0.2577 0.2102 0.081*
N8 0.29200 (17) 0.36276 (17) 0.45093 (10) 0.0494 (6)
O8 0.58011 (12) 0.24454 (12) 0.45332 (7) 0.0383 (4)
C8 0.3822 (3) 0.1455 (4) 0.18979 (16) 0.0930 (16)
H8 0.3746 0.1548 0.1563 0.112*
N9 0.3786 (6) 0.4744 (5) 0.2181 (3) 0.179 (3)
C9 0.4000 (4) 0.0706 (4) 0.2069 (2) 0.1001 (17)
H9 0.4039 0.0290 0.1849 0.120*
O9 0.0262 (5) 0.5537 (5) 0.5280 (3) 0.236 (3)
H9C −0.0109 0.5227 0.5348 0.354*
C10 0.4123 (3) 0.0556 (3) 0.2565 (2) 0.0926 (16)
H10 0.4240 0.0043 0.2678 0.111*
N10 0.85686 (16) 0.20157 (17) 0.29187 (11) 0.0488 (6)
C11 0.4071 (3) 0.1184 (2) 0.28947 (15) 0.0647 (10)
H11 0.4164 0.1093 0.3229 0.078*
N11 0.59065 (15) 0.13856 (15) 0.36634 (9) 0.0396 (5)
C13 0.38073 (18) 0.24715 (16) 0.36093 (10) 0.0344 (6)
N13 0.18932 (17) 0.21193 (18) 0.45791 (11) 0.0528 (7)
C12 0.38180 (19) 0.26154 (19) 0.30631 (11) 0.0401 (6)
N12 0.33098 (17) 0.10332 (17) 0.44434 (11) 0.0515 (7)
C14 0.49781 (19) 0.24723 (17) 0.52215 (10) 0.0373 (6)
C15 0.5734 (2) 0.25677 (18) 0.55108 (11) 0.0421 (7)
H15 0.6234 0.2619 0.5361 0.051*
C16 0.5754 (2) 0.2587 (2) 0.60129 (11) 0.0501 (8)
C17 0.5022 (3) 0.2505 (2) 0.62461 (12) 0.0575 (9)
H17 0.5038 0.2514 0.6585 0.069*
C18 0.4274 (2) 0.2410 (2) 0.59724 (12) 0.0556 (9)
H18 0.3788 0.2347 0.6134 0.067*
C19 0.4200 (2) 0.24027 (19) 0.54488 (11) 0.0444 (7)
C20 0.50583 (17) 0.24621 (16) 0.46825 (10) 0.0324 (6)
C21 0.3062 (3) 0.0655 (2) 0.40349 (16) 0.0654 (10)
H21 0.2793 0.0946 0.3780 0.078*
C22 0.3183 (3) −0.0146 (3) 0.3967 (2) 0.0858 (14)
H22 0.3005 −0.0386 0.3671 0.103*
C23 0.3563 (3) −0.0583 (3) 0.4337 (2) 0.0906 (15)
H23 0.3641 −0.1128 0.4302 0.109*
C24 0.3825 (3) −0.0208 (3) 0.4759 (2) 0.0881 (15)
H24 0.4096 −0.0493 0.5016 0.106*
C25 0.3687 (2) 0.0604 (2) 0.48046 (17) 0.0698 (11)
H25 0.3864 0.0856 0.5097 0.084*
C26 0.6347 (2) 0.1100 (2) 0.33113 (12) 0.0502 (8)
H26 0.6642 0.1459 0.3131 0.060*
C28 0.5955 (2) −0.0235 (2) 0.34638 (17) 0.0701 (11)
H28 0.5965 −0.0776 0.3394 0.084*
C27 0.6393 (3) 0.0302 (2) 0.31987 (14) 0.0643 (10)
H27 0.6711 0.0129 0.2950 0.077*
C29 0.5509 (2) 0.0051 (2) 0.38314 (17) 0.0696 (11)
H29 0.5214 −0.0295 0.4020 0.083*
C30 0.5501 (2) 0.0852 (2) 0.39186 (13) 0.0511 (8)
H30 0.5195 0.1036 0.4170 0.061*
C31 0.8508 (3) 0.1767 (3) 0.24590 (17) 0.0850 (14)
H31 0.8391 0.2142 0.2213 0.102*
C32 0.8609 (4) 0.0983 (4) 0.2324 (3) 0.120 (2)
H32 0.8575 0.0832 0.1998 0.144*
C33 0.8760 (4) 0.0434 (3) 0.2693 (3) 0.126 (3)
H33 0.8814 −0.0103 0.2619 0.151*
C34 0.8830 (4) 0.0677 (3) 0.3155 (3) 0.116 (2)
H34 0.8952 0.0316 0.3408 0.139*
C35 0.8721 (3) 0.1462 (2) 0.32525 (18) 0.0758 (12)
H35 0.8757 0.1618 0.3578 0.091*
C36 1.0032 (2) 0.3342 (2) 0.26566 (14) 0.0617 (10)
H36 0.9686 0.3255 0.2373 0.074*
C37 1.0884 (3) 0.3383 (3) 0.2622 (2) 0.0800 (13)
H37 1.1108 0.3331 0.2321 0.096*
C38 1.1401 (3) 0.3503 (3) 0.3040 (2) 0.0881 (15)
H38 1.1982 0.3528 0.3028 0.106*
C39 1.1046 (3) 0.3585 (3) 0.3471 (2) 0.0884 (15)
H39 1.1382 0.3668 0.3759 0.106*
C40 1.0182 (2) 0.3544 (3) 0.34761 (15) 0.0693 (11)
H40 0.9946 0.3605 0.3773 0.083*
C41 0.8741 (3) 0.5083 (2) 0.31126 (15) 0.0631 (10)
H41 0.9101 0.4917 0.2882 0.076*
C42 0.8700 (3) 0.5882 (3) 0.3212 (2) 0.0851 (14)
H42 0.9019 0.6245 0.3050 0.102*
C43 0.8184 (3) 0.6134 (3) 0.3553 (2) 0.0866 (14)
H43 0.8147 0.6671 0.3631 0.104*
C44 0.7716 (3) 0.5574 (3) 0.37818 (16) 0.0736 (11)
H44 0.7356 0.5728 0.4015 0.088*
C45 0.7791 (2) 0.4789 (2) 0.36584 (13) 0.0563 (9)
H45 0.7473 0.4417 0.3814 0.068*
C46 0.5251 (2) 0.4385 (2) 0.36033 (13) 0.0553 (8)
H46 0.5102 0.4180 0.3294 0.066*
C47 0.5078 (3) 0.5176 (2) 0.36945 (17) 0.0719 (11)
H47 0.4816 0.5495 0.3451 0.086*
C48 0.5297 (3) 0.5479 (2) 0.41478 (19) 0.0774 (12)
H48 0.5178 0.6006 0.4218 0.093*
C49 0.5694 (3) 0.5000 (2) 0.45000 (16) 0.0655 (10)
H49 0.5852 0.5197 0.4811 0.079*
C50 0.5850 (2) 0.4229 (2) 0.43813 (13) 0.0516 (8)
H50 0.6128 0.3907 0.4618 0.062*
C51 0.3181 (3) 0.4109 (2) 0.41701 (15) 0.0650 (10)
H51 0.3510 0.3892 0.3939 0.078*
C52 0.2999 (3) 0.4900 (2) 0.41382 (17) 0.0758 (12)
H52 0.3197 0.5207 0.3890 0.091*
C53 0.2526 (3) 0.5238 (3) 0.44738 (18) 0.0796 (13)
H53 0.2387 0.5775 0.4457 0.096*
C54 0.2257 (3) 0.4763 (3) 0.48373 (18) 0.0875 (15)
H54 0.1941 0.4973 0.5077 0.105*
C55 0.2468 (3) 0.3967 (3) 0.48392 (14) 0.0717 (11)
H55 0.2284 0.3648 0.5086 0.086*
C56 0.4011 (6) 0.5255 (8) 0.1837 (3) 0.164 (3)
H56 0.4207 0.5064 0.1549 0.197*
C57 0.3952 (6) 0.6013 (9) 0.1908 (4) 0.194 (6)
H57 0.4259 0.6365 0.1731 0.233*
C58 0.3503 (7) 0.6263 (5) 0.2202 (6) 0.201 (6)
H58 0.3326 0.6790 0.2180 0.242*
C59 0.3244 (5) 0.5803 (5) 0.2566 (3) 0.143 (3)
H59 0.2993 0.6025 0.2828 0.171*
C60 0.3359 (6) 0.5039 (5) 0.2537 (3) 0.151 (3)
H60 0.3142 0.4700 0.2763 0.181*
C61 0.0062 (7) 0.5620 (7) 0.4726 (4) 0.222 (4)
H61A −0.0425 0.5953 0.4665 0.334*
H61B −0.0045 0.5109 0.4578 0.334*
H61C 0.0536 0.5863 0.4590 0.334*
C62 0.7834 (2) 0.1190 (2) 0.44030 (13) 0.0563 (9)
H62 0.7638 0.1269 0.4078 0.068*
C63 0.8043 (3) 0.0431 (3) 0.45651 (18) 0.0789 (12)
H63 0.7980 0.0002 0.4351 0.095*
C64 0.8340 (3) 0.0312 (3) 0.5037 (2) 0.0934 (16)
H64 0.8495 −0.0197 0.5143 0.112*
C65 0.8413 (3) 0.0930 (3) 0.53541 (18) 0.0909 (16)
H65 0.8609 0.0841 0.5678 0.109*
C66 0.8198 (2) 0.1692 (3) 0.52009 (13) 0.0666 (11)
H66 0.8244 0.2112 0.5422 0.080*
C67 0.79125 (18) 0.1828 (2) 0.47167 (11) 0.0436 (7)
C68 0.77291 (18) 0.26548 (19) 0.45476 (10) 0.0407 (7)
C69 0.77531 (17) 0.28291 (17) 0.40020 (10) 0.0341 (6)
C70 0.64904 (17) 0.30409 (17) 0.29423 (9) 0.0330 (6)
C71 0.65591 (18) 0.32185 (17) 0.24138 (9) 0.0344 (6)
C72 0.73149 (18) 0.34339 (17) 0.21996 (10) 0.0370 (6)
C73 0.7230 (2) 0.3544 (2) 0.16815 (11) 0.0469 (7)
H73 0.7710 0.3669 0.1525 0.056*
C74 0.6486 (2) 0.3475 (2) 0.14038 (11) 0.0544 (9)
H74 0.6462 0.3559 0.1068 0.065*
C75 0.5769 (2) 0.3279 (2) 0.16269 (11) 0.0553 (9)
C76 0.5805 (2) 0.3146 (2) 0.21218 (10) 0.0455 (7)
H76 0.5317 0.3006 0.2265 0.055*

Source of material

The ligand was synthesized from the reaction of benzoyl hydrazine (100 mg, 0.60 mmol) and benzoate (50 mg, 0.60 mmol) according to the procedure reported earlier [4]. Yield (0.020 g, 60%).

Experimental details

The C-bound H atoms were geometrically placed (C—H = 0.95–0.98 Å) and refined as riding with U iso(H) = 1.2–1.5 U eq(C). The N-bound H atoms were located in a difference Fourier map but were refined with a distance restraint of N—H = 0.88 ± 0.01 Å, and with U iso(H) set to 1.2 U equiv(N) [1], [2], [3].

Discussion

Aldooxime and acyl compounds both containing multiple O and N atoms can participate in coordination, so the coordination ability of them are very strong, then they can show diversity in their coordination forms. A part of the multinuclear complexes have been one of the research hotspots in recent years [4], [5], [6], [7]. A lot of multinuclear metal complexes with aldooxime and acyl compounds have been reported. In this paper, a three nuclear Ni complex is reported.

The title complex is composed of three Ni atoms, two acylhydrazine ligands, nine pyridines and one methanol molecule. It is the first trinuclear Ni complex with this specific salycilate ligand. The coordination geometry of three Ni atoms is octahedral. The Ni1 atoms is bound to two carbonyl oxygens, two hydrazine nitrogens of two ligands and two nitrogens of pyridines. The bond lengths of Ni1–O are 2.020 and 2.029 Å, which are similar to the corresponding values of the reference [710]. For the Ni2 and Ni3 atoms, the octahedral geometry is realized with one carbonyl oxygen atom, one phenolate oxygen atom, one hydrazine nitrogen of ligand and three pyridine nitrogen atoms. The average bond distances of Ni–N and Ni–O for Ni2 and Ni3 are 2.123 and 2.039 Å, which is shorter than the distances of Ni1 atoms. This difference may be attributed to the difference in stereochemistry between the central and terminal Ni atoms. The neighboring Ni–Ni interatomic distances are 4.766 and 4.780 Å, respectively [10].


Corresponding author: Yang Liguo, College of Chemistry and Environmental Engineering, Anyang Institute of Technology, Anyang 455000, Henan, P. R. China, E-mail:

Funding source: Henan Province Science and Technology Research Project 501100017700

Award Identifier / Grant number: 212102210118

  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 funded by Henan Province Science and Technology Research Project (501100017700) and (212102210118).

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

References

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Received: 2022-08-23
Accepted: 2022-11-07
Published Online: 2022-11-18
Published in Print: 2023-01-27

© 2022 the author(s), published by De Gruyter, Berlin/Boston

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

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  23. Crystal structure of poly[(N,N-dimethylacetamide-κO) (μ4-2-nitroisophthalato-κ 4 O:O′:O″:O′″)manganese(II)], C11H10N2O7Mn
  24. Crystal structure of 14-O-acetyldelcosine, C26H41NO8
  25. The crystal structure of poly[(1,10-phenanthroline-κ2 N,N′)-(μ 4-2-chlorobenzene-1,3-dicarboxylato-κ5 O:O′:O″:O‴) cadmium(II)] monohydrate, C20H13CdClN2O5
  26. Crystal structure of propane-1,3-diylbis(diphenylphosphine sulfide) ethanol solvate, C27H26P2S2
  27. Crystal structure of bis{[(4-diethylamino-2-hydroxy-benzylidene)-hydrazinocarbonylmethyl]-trimethylammonium} tetrabromozincate, C32H54N8O4ZnBr4
  28. Synthesis and crystal structure of dimethyl 2,2′-(2,5-bis(4-hydroxyphenyl)-2,5-dihydrofuran-3,4-diyl)dibenzoate, C34H30O7
  29. Synthesis and crystal structure of 2-(2-oxo-2-phenylethyl)-4H-chromen-4-one, C17H12O3
  30. The crystal structure of tetra(imidazole-κ1 N)zinc(II) μ2-oxido-hexaoxido-divanadium(VI) C12H16N8O6V2Zn
  31. Crystal structure of S-2-(1-(5-methylpyridin-2-ylamino)octyl)-3-hydroxynaphthalene-1,4-dione, C24H28N2O3
  32. Crystal structure of bis(μ2-5-chloro-2-oxido-N-(1-oxido-2-oxo-2-phenylethylidene)-benzohydrazonato-κ5 N,O,O′:N′,O′′)-oktakis(pyridine-κ1 N)trinickel(II) – methanol – pyridine (1/1/1) C76H65N13Cl2Ni3O9
  33. The crystal structure of methyl 3,5-diaminobenzoate, C8H10N2O2
  34. Crystal structure of 10-(9H-carbazol-9-yl)-5H-dibenzo[a,d][7]annelen-5-one, C27H17NO
  35. Crystal structure of ethyl 1-(2-hydroxyethyl)-4-((4-methoxyphenyl)amino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate, C16H20N2O5
  36. The crystal structure of 1-(4-bromophenyl)-3-cycloheptylurea, C14H19BrN2O
  37. The crystal structure of 1,4-bis(1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-yl)-3,6-bis ((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methylene)-1,4-dialuminacyclohexane – benzene (1/2), C50H72Al2B2O4
  38. Crystal structure of bis(μ 3-diphenylphosphinato)-tetrakis(μ 2-diphenylphosphinato)-bis(diphenylphosphinato)-bis(μ 2-hydroxo)dicopper(II)-ditin(IV), C104H100O18P8Cu2Sn2
  39. Crystal structure of 3-((3,4-dichloroisothiazol-5-yl)methoxy)benzo[d] isothiazole 1,1-dioxide, C11H6Cl2N2O3S2
  40. Synthesis and crystal structure of 2-(2-(2-fluorophenyl)-2-oxoethyl)-4H-chromen-4-one, C17H11FO3
  41. The crystal structure of tris(carbonyl)-bis(carbonyl)-[μ-propane-1,2- dithiolato]-(benzyldiphenylphosphine)diiron (Fe—Fe), C27H23Fe2O5PS2
  42. Crystal structure of 1-(2-(4-chlorophenethyl)-2-hydroxy-3,3-dimethylbutyl)-1H-1,2,4-triazol-4-ium nitrate, C16H23N4O4Cl
  43. The crystal structure of 3,3′-disulfanediyldi(1H-1,2,4-triazol-5-amine) monohydrate, C4H8N8OS2
  44. The crystal structure of trans-[bis(4-methylpyridine-κN)bis(quinoline-2-carboxylato- κ 2 N,O)cadmium(II)], C32H26CdN4O4
  45. The crystal structure of ethyl 2′-hydroxy-4′,6′-dimethoxy-3-(4-methoxynaphthalen-1-yl)-5-oxo-2,3,4,5-tetrahydro-[1,1′-biphenyl]-4-carboxylate, C28H28O7
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