Home Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
Article Open Access

Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8

  • Xue-Guo Liu ORCID logo EMAIL logo , Wan-Yao Chen and Hui-Yan Pan
Published/Copyright: February 2, 2022

Abstract

C42H30N14Ni2S8, triclinic, P 1 (no. 2), a = 9.5083(17) Å, b = 10.744(2) Å, c = 12.188(2) Å, α = 80.109(4)°, β = 84.876(4)°, γ = 88.758(3)°, V = 1221.7(4) Å3, Z = 1, R gt (F) = 0.0268, wRref(F2) = 0.0701, T = 296.15 K.

CCDC no.: 2141881

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: 0.23 × 0.20 × 0.18 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 1.16 mm−1
Diffractometer, scan mode: φ and ω
θmax, completeness: 27.7°, 99%
N(hkl)measured, N(hkl)unique, Rint: 14,613, 5581, 0.027
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 4890
N(param)refined: 302
Programs: SHELX [1], Bruker [2]
Table 2:

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

Atom x y z Uiso*/Ueq
C1 0.42192 (18) 0.75001 (15) 0.93099 (13) 0.0370 (3)
C2 0.56160 (17) 0.76129 (15) 0.89510 (13) 0.0360 (3)
C3 0.63737 (19) 0.66774 (17) 0.84277 (16) 0.0446 (4)
C4 0.3417 (2) 0.64191 (18) 0.92029 (16) 0.0471 (4)
C5 0.88675 (17) 0.33807 (16) 0.80122 (15) 0.0385 (4)
H5 0.839258 0.413493 0.778913 0.046*
C6 0.97260 (18) 0.32824 (18) 0.88625 (16) 0.0468 (4)
H6 0.983144 0.396523 0.922421 0.056*
C7 1.04376 (18) 0.2163 (2) 0.91831 (16) 0.0494 (5)
H7 1.102710 0.208706 0.976057 0.059*
C8 1.02670 (18) 0.11634 (18) 0.86416 (16) 0.0476 (4)
H8 1.074516 0.040672 0.884728 0.057*
C9 0.93922 (17) 0.12861 (16) 0.78002 (15) 0.0401 (4)
H9 0.926818 0.060871 0.743592 0.048*
C10 0.78502 (17) 0.25269 (17) 0.65288 (13) 0.0383 (4)
H10A 0.829266 0.313223 0.591997 0.046*
H10B 0.780618 0.172223 0.627467 0.046*
C11 0.60006 (19) 0.41425 (16) 0.64345 (16) 0.0443 (4)
H11 0.662705 0.469753 0.597527 0.053*
C12 0.4644 (2) 0.45276 (18) 0.67121 (18) 0.0529 (5)
H12 0.434572 0.534344 0.644006 0.063*
C13 0.3736 (2) 0.3695 (2) 0.73947 (17) 0.0528 (5)
H13 0.282155 0.394997 0.759577 0.063*
C14 0.41792 (19) 0.2488 (2) 0.77794 (16) 0.0542 (5)
H14 0.356604 0.191682 0.823429 0.065*
C15 0.55263 (17) 0.21350 (17) 0.74883 (14) 0.0411 (4)
H15 0.583398 0.131821 0.774577 0.049*
C16 0.5872 (3) 0.1532 (2) 0.40578 (19) 0.0627 (6)
C17 0.6025 (3) 0.0519 (2) 0.34180 (19) 0.0719 (6)
H17A 0.681454 0.068627 0.286663 0.108*
H17B 0.518129 0.045836 0.305326 0.108*
H17C 0.618162 −0.026201 0.390825 0.108*
C18 0.8358 (2) −0.12958 (18) 0.57556 (16) 0.0477 (4)
C19 0.90563 (17) −0.24751 (15) 0.56991 (14) 0.0364 (3)
C20 1.00398 (17) −0.29073 (15) 0.64180 (14) 0.0366 (3)
C21 1.0363 (2) −0.22038 (18) 0.72606 (17) 0.0477 (4)
N1 0.2746 (2) 0.55663 (18) 0.91448 (18) 0.0706 (5)
N2 0.70046 (19) 0.59504 (17) 0.79991 (17) 0.0633 (5)
N3 0.64128 (13) 0.29584 (12) 0.68320 (10) 0.0313 (3)
N4 0.87062 (13) 0.23871 (12) 0.74947 (11) 0.0320 (3)
N5 0.7818 (2) −0.03458 (17) 0.58174 (18) 0.0729 (6)
N6 1.0604 (2) −0.16311 (19) 0.79275 (18) 0.0725 (6)
N7 0.5744 (3) 0.2312 (2) 0.4567 (2) 0.0927 (7)
Ni1 0.500000 1.000000 1.000000 0.02856 (7)
Ni2 1.000000 −0.500000 0.500000 0.03001 (8)
S1 0.33334 (4) 0.86928 (4) 0.98950 (4) 0.03823 (10)
S2 0.65479 (4) 0.89470 (4) 0.90973 (3) 0.03589 (10)
S3 0.86132 (4) −0.33534 (4) 0.47093 (4) 0.03766 (10)
S4 1.08996 (4) −0.43333 (4) 0.63615 (4) 0.03938 (10)

Source of material

All reagents and chemicals were purchased from commercial sources and used without further purification. The starting materials disodium maleonitriledithiolate and 1,1′-(methylene)bis(pyridin-1-ium)bromide were synthesized following the literature procedures [3, 4]. An aqueous solution (10 mL) of 1,1′-(methylene)bis(pyridin-1-ium)bromide (0.0661 g, 0.2 mmol) was added slowly to an aqueous solution (15 mL) of disodium maleonitriledithiolate (0.0712 g, 0.4 mmol) and NiCl2. 6H2O (0.0463 g, 0.2 mmol), and the mixture was stirred at room temperature for several minutes. A red precipitate was filtered off, washed by water and dried under vacuum. The precipitate was dissolved in acetonitrile and dimethylformamide with ether diffusion. Fourteen days later red crystals were obtained.

Experimental details

Absorption corrections were applied by using multi-scan program. The structure was refined based on F2 with the SHELXL software package. Hydrogen atoms were treated as riding atoms. The Uiso values of the hydrogen atoms were set to 1.2Ueq (C).

Comment

Much effort has been devoted to the study of square-planar [M(mnt)2]n complexes because of their structures and properties in conducting and magnetic materials, dyes, non-linear optics and catalysis [5], [6], [7], [8], [9], [10]. Recently, maleonitriledithiolate complexes have been obtained by selecting different divalent cations [11], [12], [13], [14]. These salts generally consist of [M(mnt)2]n (M = Ni(II), Pd(II), Zn(II), etc.) anions and cationic counterions. It is interesting to note that different cations or metals lead to significantly different stacking patterns. Herein, we choose 1,1′-(methylene)bis(pyridin-1-ium) as organic divalent cation to obtain the title salt. The title complex crystallizes in the triclinic space group P 1 , with two half of [Ni(mnt)2]2−, one 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) dication and one acetonitrile molecule in the asymmetric unit (see the figure). The presence of acetonitrile molecule is obviously different from the compounds previously synthesized [12], [13], [14]. Each Ni(II) ion is coordinated by four sulfur atoms, and exhibits a square-planar coordination geometry. The Ni–S bond lengths and S–Ni–S bond angles are in agreement with reported values [12]. It should be noted the title structure possesses segregated stacking column. The C–H⃛N interactions are observed between anions and cations [15]. The three-dimensional supramolecular structure is formed by such weak interactions.


Corresponding author: Xue-Guo Liu, School of Biology and Chemical Engineering, Nanyang Institute of Technology, Nanyang 473004, China, E-mail:

Funding source: Scientific and Technological Research Projects of Henan Province

Award Identifier / Grant number: 182102311077

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

  2. Research funding: This study was financially supported by Scientific and Technological Research Projects of Henan Province (182102311077).

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

References

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

2. Bruker. SMART APEX-II CCD; Bruker AXS Inc.: Madison, WI, USA, 2006.Search in Google Scholar

3. Simmons, H. E., Blomstrom, D. C., Vest, R. D. Thiacyanocarbons. II. Chemistry of disodium dimercaptomaleonitrile. J. Am. Chem. Soc. 1962, 84, 4756–4771; https://doi.org/10.1021/ja00883a029.Search in Google Scholar

4. Musilek, K., Komloova, M., Zavadova, V., Holas, O., rabinova, M., Pohanka, M., Dohnal, V., Nachon, F., Dolezal, M., Kuca, K., Jung, Y. S. Preparation and in vitro screening of symmetrical bispyridinium cholinesterase inhibitors bearing different connecting linkage-initial study for Myasthenia gravis implications. Bioorg. Med. Chem. Lett 2010, 20, 1763–1766; https://doi.org/10.1016/j.bmcl.2010.01.034.Search in Google Scholar

5. Tanaka, H., Okano, Y., Kobayashi, H., Suzuki, W., Kobayashi, A. A Three-dimensional synthetic metallic crystal composed of single-component molecules. Science 2001, 291, 285–287; https://doi.org/10.1126/science.291.5502.285.Search in Google Scholar

6. Bigoli, F., Chen, C. T., Wu, W. C., Deplano, P., Mercuri, M. L., Pellinghelli, M. A., Pilia, L., Pintus, G., Serpe, A., Trogu, E. F. [Ni(R2pipdt)2](BF4)2 (R2pipdt = 1,4-disubstituted- piperazine-3,2-dithione) as useful precursors of mixed-ligand dithiolenes of interest for non-linear optics. Chem. Commun. 2001, 2246–2247; https://doi.org/10.1039/b106064n.Search in Google Scholar

7. Robertson, N., Cronin, L. Metal bis-1,2-dithiolene complexes in conducting or magnetic crystalline assemblies. Coord. Chem. Rev. 2002, 227, 93–127; https://doi.org/10.1016/s0010-8545(01)00457-x.Search in Google Scholar

8. Duan, H. B., Ren, X. M., Meng, Q. J. One-dimensional (1D) [Ni(mnt)2]− based spin-Peierls-like complexes: structural, magnetic and transition properties. Coord. Chem. Rev. 2010, 254, 1509–1522; https://doi.org/10.1016/j.ccr.2009.12.021.Search in Google Scholar

9. Wang, P. Crystal structure of Mn(II)(H2O)(2,13-dimethyl-3,6,9,12,18-pentaazabicyclo[12.3.1]octadeca-1(18),2,12,14,16-pentaene)-bis-(maleonitriledithiolate)nickel(II), C23H25MnN9NiOS4. Z. Kristallogr. N. Cryst. Struct. 2012, 227, 511–512; https://doi.org/10.1524/ncrs.2012.0244.Search in Google Scholar

10. Nishijo, J., Uchida, M., Enomoto, M., Akita, M. A chromium(III) bis-acetylide complex containing a trans-diethyl-ethylenedithio-substituted tetrathiafulvalene (TTF) derivative: synthesis, crystal structures, and magnetic properties. Transit. Met. Chem. 2021, 46, 373–380; https://doi.org/10.1007/s11243-021-00453-9.Search in Google Scholar

11. Yan, W. H., Ji, E. Y., Shen, M. L., Li, Z. Y., Li, X., Xu, X. L. Two ion-pair complexes constructed by [M(mnt)2]n−(M = Ni, Co, mnt = maleonitriledithiolate): syntheses, characterization and thermal stability. Chin. J. Struct. Chem. 2015, 34, 306–312.Search in Google Scholar

12. Yan, W. H., Pan, H. Y. Crystal structure of 1,4-bis(methylpyridinium benzene) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S) nickel(II), C26H18N6NiS4. Z. Kristallogr. N. Cryst. Struct. 2021, 236, 107–108; https://doi.org/10.1515/ncrs-2020-0407.Search in Google Scholar

13. Yan, W. H., Liu, X. G., Shen, M. L., Pan, H. Y. Crystal structure of 1,1′-(1,4-phenylenebis(methylene))bis(pyridin-1-ium) bis (1,2-dicyanoethene-1,2-dithiolato-κ2S:S) zinc(II), C26H18N6ZnS4. Z. Kristallogr. N. Cryst. Struct. 2021, 236, 533–535; https://doi.org/10.1515/ncrs-2020-0624.Search in Google Scholar

14. Liu, X. G., Pan, H. Y. Crystal structure of 1,1′-(1,3-phenylenebis (methylene))bis(pyridm)bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)palladium(II), C26H18N6PdS4. Z. Kristallogr. N. Cryst. Struct. 2021, 236, 1247–1249; https://doi.org/10.1515/ncrs-2021-0292.Search in Google Scholar

15. Jeffrey, G. A. Hydrogen-bonding: an update. Crystallogr. Rev. 2003, 9, 135–176; https://doi.org/10.1080/08893110310001621754.Search in Google Scholar

Received: 2021-11-09
Accepted: 2022-01-13
Published Online: 2022-02-02
Published in Print: 2022-04-26

© 2022 Xue-Guo Liu et al., published by De Gruyter, Berlin/Boston

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

Articles in the same Issue

  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
Downloaded on 22.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2021-0434/html
Scroll to top button