Home Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
Article Open Access

Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2

  • Lingyi Shen , Na Xu , Mengna Jiang , Jiang Zhao , Xiaoling Xu , Xian-Jiong Yang and Qi-Long Zhang ORCID logo EMAIL logo
Published/Copyright: November 3, 2023

Abstract

C30H40N2NiO2, orthorhombic, Pnma (no. 62), a = 12.8114(19) Å, b = 21.301(3) Å, c = 10.6536(16) Å, V = 2907.3(8) Å3, Z = 4, R gt(F) = 0.0290, wR ref(F 2) = 0.0808, T = 273(2) K.

CCDC no.: 2292959

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: Purple block
Size: 0.32 × 0.25 × 0.22 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.69 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 25.0°, >99 %
N(hkl)measured, N(hkl)unique, R int: 17,151, 2634, 0.028
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2386
N(param)refined: 172
Programs: SHELX [1, 2], Olex2 [3], Diamond [4]
Table 2:

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

Atom x y z U iso*/U eq
C1 0.49304 (12) 0.28463 (7) 0.44437 (15) 0.0339 (4)
C2 0.58099 (16) 0.32077 (10) 0.5023 (2) 0.0639 (6)
H2A 0.5643 0.3647 0.5022 0.096*
H2B 0.6436 0.3139 0.4548 0.096*
H2C 0.5914 0.3069 0.5871 0.096*
C3 0.39049 (12) 0.37605 (7) 0.41154 (15) 0.0315 (3)
C4 0.33668 (14) 0.39501 (8) 0.51984 (16) 0.0402 (4)
C5 0.31313 (15) 0.45851 (9) 0.5324 (2) 0.0512 (5)
H5 0.2777 0.4723 0.6035 0.061*
C6 0.34122 (17) 0.50120 (9) 0.4417 (2) 0.0576 (5)
H6 0.3243 0.5434 0.4514 0.069*
C7 0.39429 (17) 0.48156 (9) 0.3368 (2) 0.0522 (5)
H7 0.4134 0.5110 0.2765 0.063*
C8 0.42029 (13) 0.41856 (8) 0.31852 (16) 0.0380 (4)
C9 0.30435 (18) 0.34916 (10) 0.62179 (19) 0.0569 (5)
H9 0.3244 0.3070 0.5941 0.068*
C10 0.3612 (3) 0.36240 (18) 0.7452 (3) 0.1153 (12)
H10A 0.4351 0.3635 0.7304 0.173*
H10B 0.3454 0.3299 0.8046 0.173*
H10C 0.3387 0.4021 0.7780 0.173*
C11 0.1866 (2) 0.34903 (15) 0.6436 (3) 0.0876 (9)
H11A 0.1652 0.3893 0.6748 0.131*
H11B 0.1691 0.3172 0.7038 0.131*
H11C 0.1514 0.3405 0.5659 0.131*
C12 0.47950 (16) 0.39838 (9) 0.20219 (16) 0.0462 (4)
H12 0.4872 0.3526 0.2056 0.055*
C13 0.5893 (2) 0.42691 (15) 0.1991 (3) 0.0824 (8)
H13A 0.5842 0.4718 0.1958 0.124*
H13B 0.6258 0.4120 0.1263 0.124*
H13C 0.6267 0.4148 0.2733 0.124*
C14 0.4192 (2) 0.41421 (14) 0.0828 (2) 0.0807 (8)
H14A 0.3502 0.3968 0.0879 0.121*
H14B 0.4548 0.3968 0.0116 0.121*
H14C 0.4146 0.4590 0.0739 0.121*
C15 0.1822 (2) 0.2500 0.3443 (3) 0.0495 (7)
C16 0.3328 (2) 0.2500 0.1435 (3) 0.0483 (6)
N1 0.41037 (10) 0.30968 (6) 0.39643 (11) 0.0283 (3)
Ni1 0.31582 (2) 0.2500 0.30825 (3) 0.03177 (13)
O1 0.09369 (17) 0.2500 0.3555 (3) 0.0926 (9)
O2 0.3380 (2) 0.2500 0.0373 (2) 0.0818 (7)

1 Source of materials

Under a nitrogen atmosphere, the grass-green Ni–Ni-bonded complex [{Ni I (μ–L)}2] (0.232 g, 0.25 mmol) (L = N,N2-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine), which was synthesized from the literature [5, 6], was dissolved in 20 ml anhydrous n-hexane at room temperature. A CO gas stream bubbled into the solution which was stirred for 0.5 h. The color of the reaction mixture changed from grass green to purple. After then, the mixture was filtered and concentrated by vacuum to about 6 ml. The solution was stored at room temperature for about one week to afford purple crystals with yield of 82 % (0.213 g).

2 Experimental details

SADABS [1] was applied for absorption correction and the structure was solved and refined to convergence using the SHELXL-2014 programs [2] and OLEX2 [3]. All hydrogen atoms were positioned geometrically, with the d(C–H) = 0.97–0.99 Å, U iso(H) = 1.2 times U eq(C) and U iso(H) = 1.5 times U eq(O).

3 Comment

Many nickel complexes have been verified as good catalysts for organic chemical reactions, especially in olefin polymerization [7, 8] and alkyne cyclization [9, 10]. α-Diimine is widely used in metal coordination chemistry as a serial of nitrogen-containing bidentate ligands which can form different coordination structures with metals because of their electronic effects. Based on the above advantages and research results, α-diimide is also favored by researchers in the synthesis of metal-organic catalysts. Here, we report a crystal structure of mononuclear nickel carbonyl complex.

In the title structure, the nickel is coordinated with four atoms those two nitrogen atoms of the ligand and two carbon atoms of CO. The title molecule is located on a mirror plane. Moreover, C1, N1, Ni1, N1#, C1# are in the same plane which is perpendicular to the plane of O1–C15–Ni1–C16–O2 (dihedral angle is 90°). In addition, as a metal catalyst, it is important to determine the oxidation state of its ligand and metal. Based on the literature [11, 12], the central core bond lengths (C1–C1# (1.475(3) Å) and C1–N1 (1.291(2)) refer to the neutral form of the ligand. Moreover, the C–O bond lengths are 1.140(3) Å and 1.133(4) Å, respectively, so the triple-bond is still retained, and therefore, the central nickel valence state has zero valence, which provides potential as a catalyst.


Corresponding author: Qi-Long Zhang, School of Basic Medical Science, Guizhou Medical University, Guiyang, 550025, People’s Republic of China, E-mail:

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

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

  3. Research funding: Guizhou Medical University Startup Project of Doctor Scientific Research (grant number YJ2020-BK024), the Cultivation program of the Guizhou Medical University, (20NSP012), the Guizhou Provincial Department of Education Foundation KY [2022]229 and the Provincial General Project of University Student Innovation and Entrepreneurship Fund (No. S202110660004).

References

1. Sheldrick, G. M. Program SADABS: Area-Detector Absorption Correction; University of Göttingen: Germany, 1996.Search in Google Scholar

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

3. 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

4. Brandenburg, K. DIAMOND. Visual Crystal Structure Information System. Ver.0; Crystal Impact: Bonn, Germany, 2015.Search in Google Scholar

5. Dong, Q., Yang, X.-J., Gong, S., Luo, Q., Li, Q.-S., Su, J.-H., Zhao, Y., Wu, B. Distinct stepwise reduction of a nickel–nickel-bonded compound containing an α-diimine ligand: from perpendicular to coaxial structures. Chem. Eur. J. 2013, 19, 15240–15247; https://doi.org/10.1002/chem.201302463.Search in Google Scholar PubMed

6. Dong, Q., Su, J.-H., Gong, S., Li, Q.-S., Zhao, Y., Wu, B., Yang, X.-J. Nickel complexes with two types of noninnocent ligands: α-diimine and phenazine. Organometallics 2013, 32, 2866–2869; https://doi.org/10.1021/om400130m.Search in Google Scholar

7. Killian, C. M., Tempel, D. J., Johnson, L. K., Brookhart, M. Living polymerization of α-olefins using NiII-α-diimine catalysts. Synthesis of new block polymers based on α-olefins. J. Am. Chem. Soc. 1996, 118, 11664–11665; https://doi.org/10.1021/ja962516h.Search in Google Scholar

8. Léonard, N. G., Yruegas, S., Ho, S. C., Sattler, A., Bezdek, M. J., Chirik, P. J. Synthesis of cationic, dimeric α-diimine nickel hydride complexes and relevance to the polymerization of olefins. Organometallics 2020, 39, 2630–2635; https://doi.org/10.1021/acs.organomet.0c00257.Search in Google Scholar

9. Saito, S., Yamamoto, Y. Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives. Chem. Rev. 2000, 100, 2901–2916; https://doi.org/10.1021/cr990281x.Search in Google Scholar PubMed

10. Shen, L., Zhao, Y., Luo, Q., Li, Q.-S., Liu, B., Redshaw, C., Wu, B., Yang, X.-J. Cyclotrimerization of alkynes catalyzed by a self-supported cyclic tri-nuclear nickel(0) complex with α-diimine ligands. Dalton Trans. 2019, 48, 4643–4649; https://doi.org/10.1039/c9dt00819e.Search in Google Scholar PubMed

11. Dong, Q., Zhao, Y., Su, Y., Su, J.-H., Wu, B., Yang, X.-J. Synthesis and reactivity of nickel hydride complexes of an α-diimine ligand. Inorg. Chem. 2012, 51, 13162–13170; https://doi.org/10.1021/ic301392p.Search in Google Scholar PubMed

12. Herebian, D., Bothe, E., Neese, F., Weyhermüller, T., Wieghardt, K. Molecular and electronic structures of bis-(o-diiminobenzosemiquinonato)metal(II) complexes (Ni, Pd, Pt), their monocations and -anions, and of dimeric dications containing weak metal-metal monds. J. Am. Chem. Soc. 2003, 125, 9116–9128; https://doi.org/10.1021/ja030123u.Search in Google Scholar PubMed

Received: 2023-09-06
Accepted: 2023-10-25
Published Online: 2023-11-03
Published in Print: 2023-12-15

© 2023 the author(s), 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 bis(dimethylammonium) poly[(μ4-1,1′-(1,4-phenylenebis(methylene))bis(1H-pyrazole-3,5-dicarboxylato))-κ6O1, N2:O2:O3:O1′,N2′]nickel (II)], C22H26N6NiO8
  4. Hydrothermal synthesis and crystal structure of catena-poly[diaqua-bis(μ2-4-((pyridin-4-ylmethyl)amino)benzoato-κ2N:O)cobalt(II)] 4,4′-bipyridine – water (1/2/2)
  5. Crystal structure of (2S,3S,4S,5S, Z)-2,3,5,6-tetrakis(benzyloxy)-4-hydroxyhexanal oxime, C34H37NO6
  6. The crystal structure of hexakis(3-thiophenecarboxylato-κ2O,O″)-bis(1,10-phenanthroline-κ2N,N′) trimanganese(II), C54H34N4O12S6Mn3
  7. Crystal structure of catena-poly[(μ2-1,4-di(pyridin-4-yl)benzene-κ2N:N′)-(4-bromobenzoate-κ2O:O′)-(μ-2-bromobenzoate-κ2O,O′)nickel(II)] – water (2/1), C30H21Br2N2NiO4.5
  8. The crystal structure of poly[(μ3-1,3-phenylenedioxydiacetate-κ5O,O,O′,O″,O‴)-bis(4′-(4-(1H-imidazol-1-yl)phenyl)-4,2′:6′,4″-terpyridine-kN) cadmium(II)], C58H42CdN10O6
  9. The crystal structure of 5-chloro-6′-methyl-3-(4-(methylsulfonyl)phenyl)-[2,3′-bipyridin]-1′-ium 4-methylbenzenesulfonate
  10. Crystal structure of poly[(μ-benzoato)-(μ-cis-4–hydroxy-D-proline)lithium], C12H14LiNO5
  11. The crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O)-copper(II)] monohydrate, C7H6NO6ICu
  12. The crystal structure of catena-[diaqua-(4-acetylphenoxyacetato-κ2O,O)-bis(4-acetylphenoxyacetato-κ3O,O:O)-dihydrate-lanthanum(III)]–4,4′-bipyridine (2/1), C35H35NO14La
  13. The crystal structure of catena-poly[(4-iodopyridine-2,6-dicarboxylato-κ4 O,N,O′,O′′)(4-imidazol-1-yl-pyridine-κN)copper(II)], C15H9N4O4ICu
  14. Crystal structure of polybis(μ 4-3,5-dicarboxylatopyrazol-1-yl)-bis(N,N-dimethylformamide)tri-copper(II)–acetonitrile (1/2), C20H22Cu3N8O10
  15. Crystal structure of poly[(μ2-5-hydroxy-isophthalato-κ4O,O′:O″,O‴)-(μ2-1,5-bis(imidazol-2-methyl)pentane-κ2N:N′)cadmium(II)], C21H24CdN4O5
  16. The crystal structure of poly[bis(μ2-1,4-bi(1-imidazolyl)benzene-κ2N:N′)bis(μ2-4,4′-methylenebis(3-hydroxy-2-naphthoate)-κ2O:O′)cobalt(II)], C35H24CoN4O6
  17. The crystal structure of a cobalt-vanadium-oxido hydrate
  18. The crystal structure of catena-poly[(μ 2-2H-1,2,3-triazole-4,5-dicarboxylato-κ 2 O, O′)-(μ 2-1,3-bis((1H-imidazol-1-yl)methyl)benzene-κ 2 N,N′) zinc(II)], C18H15N7O4Zn
  19. Crystal structure of poly[diaqua-(bis(m2-1,4-bis(imidazol-1-ylmethyl)benzene)-κ2N,N′-manganese] dichloride, C28H32MnN8O2Cl2
  20. The crystal structure of 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino [3,2-a]isoquinolin-7-ium (E)-3-(4-nitrophenyl)acrylate pentahydrate, C29H34N2O13
  21. Crystal structure of poly[(μ6-ammoniotris(methylene))tris(hydrogen phosphonato)cadmium(II)], C3H10CdNO9P3
  22. Crystal structure of Zn2[(1,1′-(hexane-1,6-diyl)bis(3-(pyridin-3-yl)urea))·(H2O)2·(DMF)2·(SO4)2], C24H50N8O18S2Zn2
  23. The crystal structure of 2-anilino-1,4-naphthoquinone, C10H11NO2
  24. Crystal structure of (E)-2-(2-(4-(diethylamino)styryl)-1-ethyl-1,4-dihydroquinolin-4-yl) malononitrile, C26H26N4
  25. Crystal structure of ethyl 2-((2,6-dichloro-4-(cyanomethyl)phenyl) amino)benzoate, C17H14Cl2N2O2
  26. Synthesis and crystal structure of 2-(3-oxo-3-phenylpropyl)isoindoline-1,3-dione, C17H13NO3
  27. The crystal structure of bis(acetonitrile-κ1N)tetrakis(μ2-2,6-difluorobenzoato-κ2O:O′)rhodium(II) (Rh–Rh), C32H18F8O8N2Rh2
  28. The crystal structure of a new polymorph of 6-hydroxy-2-naphthoic acid, C11H8O3
  29. The crystal structure of [(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)-2,2′-bipyridine-κ2N-copper(II)] tetrahydrate, C22H23N3O9Cu
  30. The crystal structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-(2-oxo-2H-chromen-6-yl)-2,5-dihydro-1H-pyrrole-3-carboxylate, C23H19NO7
  31. Crystal structure of 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one, C10H10O2
  32. Crystal structure of bis(tetrapropylammonium) dodecacarbonyltetratelluridotetraferrate(2-), (Pr4N)2[Fe4Te4(CO)12]
  33. The crystal structure of poly[bis(μ2−3−aminopyridine−4−carboxylatoκ2N:O)Zinc(II)], [Zn(C6H5N2O2)2] n
  34. The crystal structure of methyl 5-nitro-2-(tosyloxy)benzoate, C15H13NO7S
  35. The crystal structure of 18-crown-6 ― tetraaqua-dichlorido-di-μ2-chloridodicopper(II) (2/1), C12H32O10Cu2Cl4
  36. Crystal structure of 6,6a,7,8,9,10-hexahydro-5H-pyrazino [2,3-e]pyrido[1,2-a]pyrazine, C10H14N4
  37. Crystal structure of catena-poly-{diaqua-bis[μ-(((4-chlorophenyl)sulfonyl)glycinato-κO)](μ2-4, 4′-bipyridine-κ2N:N′)cobalt(II)} dihydrate, C26H30Cl2CoN4O12S2
  38. Crystal structure of bis{N′-[1,3-diphenylprop-2-en-1-ylidene]-N-phenylcarbamohydrazonothioato}zinc(II), C44H36N6S2Zn
  39. Crystal structure of tetraaqua-bis(((4-chlorophenyl)sulfonyl)glycinato-κO)cobalt(II) dihydrate, C16H26Cl2CoN2O14S2
  40. Crystal structure of 2-(5-phenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenol, C24H19N3O
  41. Crystal structure of 2-((2-fluoro-4-(trifluoromethyl)phenyl)(hydroxy)methyl)-7-methoxy-3,4-dihydronaphthalen-1((2H))-one, C19H16F4O3
  42. Crystal structure of 2-amino-4-(2-fluoro-3-(trifluoromethyl)phenyl)-9-methoxy-1,4,5,6-tetrahydrobenzo[h]quinazolin-3-ium chloride, C20H18ClF4N3O
  43. Crystal structure of (2-phenylimino methylquinoline-κ 2 N,N′)-bis(1–phenylpyrazole-κ 2 C,N)-iridium(III) hexafluorophosphate, C34H26F6IrN6P
  44. Crystal structure of (3-hydroxy-4-methoxyphenyl)(pyrrolidin-1-yl)methanone, C12H15NO3
  45. The crystal structure of bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)] C6H18O2S2NaInBr6
  46. Crystal structure of N-cyclopropyl-3-hydroxy-4-methoxybenzamide, C11H13NO3
  47. The crystal structure of (bis(benzimidazol-2-yl-methyl)amine-κ3N,N,N )-(dihydrogen L-malate-κ2O,O )copper(II) perchlorate dihydrate, CuC20H24ClN5O12
  48. Crystal structure of (1E,1′E)-4,4′-(9,9-diethyl-9H-fluorene-2,7-diyl)dibenzaldehyde dioxime, C31H28N2O2
  49. Crystal structure of diethyl 1,9-bis(4-fluorophenyl)-4,6-diphenylhexahydro-3H-2,7,3,5-(epimethanetriyliminomethanetriyl)cyclopenta [b]pyridine-3,7(2H)-dicarboxylate, C40H36F2N2O4
  50. Crystal structure of bis(benzene-1 carboxylato-O 3,5-carboxyl-κ1O)-[(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) ─ benzene-1,3,5-tricarboxylic acid ─ water (1/2/4), C52H66N4NiO28
  51. Crystal structure of 1,4-dibromo-2,5-bis(2-methoxyethoxy)benzene-1,4-diol, C12H16Br2O4
  52. Crystal structure of dicarbonyl[N,N′-(1,2-dimethyl-1,2-ethanediylidene)bis[2,6-bis(1-methylethyl)benzenamine]-N,N′]nickel(0), C30H40N2NiO2
  53. Crystal structure of 1,4-dibromo-2,5-bis(prop-2-yn-1-yloxy)benzene, C12H8Br2O2
  54. Crystal structure of O-(3-(benzo[d]thiazol-2-yl)naphthalen-2-yl) O-phenyl carbonothioate, C24H15NO2S2
  55. The crystal structure of (E)-4-fluoro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15FN2O2
  56. Crystal structure of (E)-1-(benzo[d]thiazol-2-yl)-N-(4,5-dihydropyren-2-yl)methanimine, C24H16N2S
  57. Crystal structure of 3-((4-bromophenyl)thio)-1H-indole, C14H10BrNS
  58. Synthesis and crystal structure of 1-((7-hydroxy-3-(4-hydroxy-3-nitrophenyl)-4-oxo-4H-chromen-8-yl)methyl)piperidin-1-ium-4-carboxylate monohydrate, C22H22N2O9
  59. Synthesis and crystal structure of (3E,5S,10S,13S,14S,17Z)-17-ethylidene-10,13-dimethylhexadecahydro-3H-cyclopenta[α]phenanthren-3-one O-(methacryloyl) oxime, C50H74N2O4
  60. Crystal structure of the hydrogen storage active phase La12Mg46LiMn
  61. The crystal structure of the salt: 4-((1,3-dioxoisoindolin-2-yl)carbamoyl)pyridine-1-ium 2-carboxybenzoate, C14H10N3O3·C8H5O4
  62. Crystal structure of (2-(2-pyridine)-benzimidazole-κ2 N,N′)-bis(1-phenylpyrazole-κ2 C,N)iridium(III) hexafluorophosphate, C30H22F6IrN7P
  63. Crystal structure of dichlorido-bis[2-(2,4-difluorophenyl)pyridine-κ1N]platinum(II), C22H14Cl2F4N2Pt
  64. Crystal structure of (5R,8R,9R,10R,12R,13R,14R, 17S,17Z)-2-((3-fluoropyridin-4-yl)methylene)-12-hydroxy-4,4,8,10,14-pentamethyl-17-((R)-2,6,6-trimethyltetrahydro-2H-pyran-2-yl)hexadecahydro-3H-cyclopenta[a]phenanthren-3-one, C36H52FNO3
Downloaded on 21.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2023-0399/html
Scroll to top button