Startseite Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
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Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O

  • Xu Liu und Xiang-Ru Meng ORCID logo EMAIL logo
Veröffentlicht/Copyright: 31. Januar 2022

Abstract

C16H20N4NiO14, orthorhombic, Pnma (No. 62), a = 7.1945(2) Å, b = 16.1805(4) Å, c = 17.7912(5) Å, V = 2071.08(10) Å3, Z = 4, Rgt(F) = 0.0353, wRref(F2) = 0.0997, T = 293(2) K.

CCDC no.: 2142301

The title complex 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: Blue block
Size: 0.21 × 0.19 × 0.15 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.02 mm−1
Diffractometer, scan mode: Bruker D8 VENTURE PHOTON, φ and ω
θmax, completeness: 27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint: 19,289, 2457, 0.044
Criterion for Iobs, N(hkl)gt: Iobs > 2σ(Iobs), 2071
N(param)refined: 173
Programs: SHELX [1], Bruker [2, 3]
Table 2:

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

Atom x y z Uiso*/Ueq
Ni1 0.85106 (6) 0.750000 −0.02377 (2) 0.02858 (14)
O1 0.8891 (3) 0.64733 (10) −0.09459 (9) 0.0380 (4)
O2 0.8422 (3) 0.51153 (10) −0.09723 (9) 0.0417 (4)
O3 0.7149 (3) 0.40744 (10) −0.01041 (10) 0.0411 (4)
H3 0.761797 0.443422 −0.036739 0.062*
O4 0.5869 (3) 0.40029 (10) 0.10246 (10) 0.0462 (5)
O5 0.5726 (4) 0.750000 −0.05902 (15) 0.0439 (6)
H5 0.525959 0.789800 −0.083862 0.066*
O6 1.1317 (4) 0.750000 −0.00514 (17) 0.0472 (6)
H6 1.190801 0.795420 −0.007356 0.071*
O7 0.5062 (3) 0.49183 (12) 0.24964 (10) 0.0512 (5)
H7A 0.568851 0.484683 0.289612 0.077*
H7B 0.477481 0.441742 0.241101 0.077*
N1 0.7931 (3) 0.65986 (11) 0.05063 (10) 0.0276 (4)
N2 0.6759 (3) 0.56915 (11) 0.12886 (10) 0.0288 (4)
H2 0.629388 0.548025 0.169032 0.035*
C1 0.8400 (3) 0.58154 (14) −0.06440 (13) 0.0316 (5)
C2 0.7783 (3) 0.58545 (13) 0.01493 (12) 0.0283 (4)
C3 0.7058 (3) 0.52823 (13) 0.06308 (12) 0.0286 (4)
C4 0.6643 (3) 0.43920 (14) 0.05327 (14) 0.0328 (5)
C5 0.7319 (3) 0.64909 (13) 0.12055 (12) 0.0272 (4)
C6 0.7391 (3) 0.70621 (13) 0.18527 (11) 0.0270 (4)
C7 0.7506 (3) 0.66589 (14) 0.25481 (12) 0.0350 (5)
H7 0.755439 0.608457 0.255346 0.042*
C8 0.7550 (4) 0.70717 (15) 0.32219 (12) 0.0381 (5)
H8 0.757917 0.678048 0.367237 0.046*
O8a 0.451 (3) 0.3117 (7) 0.2578 (7) 0.252 (10)
O8′a 0.3126 (16) 0.3409 (5) 0.2470 (6) 0.129 (3)
  1. aOccupancy: 0.5.

Source of material

The reagents used in this paper are purchased from commercial sources without further purification. An aqueous solution (2 mL) of NiCl2·4H2O (0.02 mmol) was added dropwise to a methanol solution (2 mL) of 2,2′-(1,2-phenylene)bis(1H-imidazole-4,5-dicarboxylic acid) (H6Phbidc, 0.02 mmol). A clear solution was obtained after filtration and placed in a closed container at room temperature. Light blue crystals can be obtained after four weeks (yield 51%, based H6Phbidc).

Experimental details

Hydrogen atoms bound to C and N atoms were positioned geometrically and refined as riding atoms, with C–H = 0.93 Å and N–H = 0.86 Å. H atoms of the nondeprotonated carboxylic acid groups were refined as riding atoms, with O–H = 0.82 Å. H atoms on O5, O6, O7 were found according to the residual electron-density peaks around each water O atom and the directions of hydrogen bonds, and were then locked in position and included with O–H = 0.85 Å. All H atoms were refined with Uiso(H) = 1.2 Ueq(C, N) and 1.5 UeqO. One guest water molecule (O8) is disordered and the hydrogen atoms of this water molecule could not be located in the difference Fourier map.

Comment

1H-Imidazole-4,5-dicarboxylic acid and its derivatives, such as 2-(hydroxymethyl)-1H-imidazole-4,5-dicarboxylic acid, 2-(pyridin-4-yl)-1H-imidazole-4,5-dicarboxylic acid, 2,2′-(1,2-phenylene)bis(1H-imidazole-4,5-dicarboxylic acid), 2-phenyl-1H-imidazole-4,5-dicarboxylic acid, 2-(1H-tetrazol-1-yl)-1H-imidazole-4,5-dicarboxylic acid, 2,2′-(ethane-1,2-diyl)bis(1H-imidazole-4,5-dicarboxylic acid), are good linkers and have been widely used in the synthesis of new coordination complexes (CPs) since they contain not only N-donors but also O-donors, which have abundant coordination modes and can lead to CPs with various structures and interesting properties [4], [5], [6], [7], [8], [9], [10], [11], [12]. Among the reported ligands, 2,2′-(1,2-phenylene)bis(1H-imidazole-4,5-dicarboxylic acid) (H6Phbidc), and corresponding deprotonated anions are excellent ligands as there are four potential N-donors and eight potential O-donors and can coordinate to almost all soft and hard metal ions with various coordination modes. Up to now, only a small number of CPs based on H6Phbidc have been reported [8, 13, 14]. In order to further enrich the categories and numbers of CPs based on this ligand, we synthesized the title compound.

The asymmetric unit of the title structure consists of one half of Ni(II) ion, one half of 2,2′-(1,2-phenylene)bis(1H-imidazole-4,5-dicarboxylate anion (H4Phbidc2−), two halfs of coordination water molecules and two uncoordinated water molecules. Each Ni1 ion is six-coordinated and located in a distorted octahedral NiN2O4 coordination environment formed by two N atoms (N1 and N1#1) and two O atoms (O1 and O1#1) from one H4Phbidc2− anion and by two water molecules (O5 and O6). The Ni–N bond lengths is 2.0133(18) Å and the Ni–O bond lengths are 2.046(3), 2.099(3), 2.1028(16) and 2.1029(16) Å, respectively; these values are within the normal ranges and close to those reported in other Ni(II) complexes [15], [16], [17]. The bond angles of O6–Ni1–O5, N1–Ni1–O1#1 and N1#1–Ni1–O1 are 171.94(12)°, 173.30(7)° and 173.30(7)°, respectively. The other bond angles around the Ni1 ion are more or less deviated from the ideal values (81.29(7)°–95.63(8)°). There are O–H⋯O intramolecular hydrogen bonds between carboxyl and carboxylate groups, N–H⋯O intermolecular hydrogen bonds between imidazole units and solvent water molecules and O–H⋯O intermolecular hydrogen bonds involving coordination water molecules, solvent water molecules and carboxylate groups. Furthermore, there are π–π stacking interactions between C6/C7/C8/C6#1/C7#1/C8#1 benzene rings with a centroid-centroid distance of 3.6002(1) Å, which are in the range for common π-π interactions [9, 18, 19]. [Ni(H4Phbidc)(H2O)2] molecules are linked by the above hydrogen bonds and π–π interactions, resulting in a three-dimensional supramolecular architecture in the solid state.


Corresponding author: Xiang-Ru Meng, College of Chemistry, Green Catalysis Center, Zhengzhou University, 450001, Henan, P. R. China, E-mail:

Funding source: National Natural Science Foundation

Award Identifier / Grant number: 202010459001

Acknowledgements

This work was financially supported by the National Natural Science Foundation (no. 202010459001).

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

  2. Research funding: National Natural Science Foundation (no. 202010459001).

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

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Received: 2021-12-04
Accepted: 2022-01-15
Published Online: 2022-01-31
Published in Print: 2022-04-26

© 2021 Xu Liu and Xiang-Ru Meng, published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
  4. The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
  5. Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
  6. Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
  7. Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
  8. The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
  9. Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
  10. The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
  11. The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
  12. Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
  13. The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
  14. Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
  15. The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
  16. Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
  17. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
  18. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
  19. Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
  20. Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
  21. The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
  22. The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
  23. The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
  24. The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
  25. Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
  26. The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
  27. The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
  28. Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
  29. The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
  30. Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
  31. The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
  32. The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
  33. The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
  34. Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
  35. The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
  36. The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
  37. The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
  38. Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
  39. Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
  40. Crystal structure of a second modification of Pachypodol, C18H16O7
  41. Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
  42. The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
  43. The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
  44. The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
  45. Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
  46. The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
  47. Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
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