Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions

Abderezak Addala; Zouaoui Setifi; Yukio Morimoto; Benãt Artetxe; Takashi Matsumoto; Juan M. Gutiérrez-Zorrilla; Christopher Glidewell

doi:10.1107/S2056989018015426

Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions

Abderezak Addala, Zouaoui Setifi^*, Yukio Morimoto, Benãt Artetxe, Takashi Matsumoto, Juan M. Gutiérrez-Zorrilla, Christopher Glidewell

^*Corresponding author for this work

School of Chemistry

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Abstract

Structures are reported for six closely related salts of tris(bipyridyl)iron(II) cations, namely tris(2,2′-bipyridine)iron(II) bis(1,1,3,3-tetracyano-2-methoxypropenide) 0.776-hydrate, [Fe(C₁₀H₈N₂)₃](C₈H₃N₄O)₂.0.776H₂O, (I), tris(2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(propylsulfanyl)propenide perchlorate, [Fe(C₁₀H₈N₂)₃](C₁₀H₇N₄S)(ClO₄), (II), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-methoxypropenide tetrafluoridoborate ethanol 0.926-solvate, [Fe(C₁₂H₁₂N₂)₃](C₈H₃N₄O)(BF₄).0.926C₂H₂O, (III), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-ethoxypropenide tetrafluoridoborate, [Fe(C₁₂H₁₂N₂)₃](C₉H₅N₄O)(BF₄), (IV), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(ethylsufanyl)propenide tetrafluoridoborate, [Fe(C₁₂H₁₂N₂)₃](C₉H₅N₄S)(BF₄), (V), and tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-propoxypropenide tetrafluoridoborate, [Fe(C₁₂H₁₂N₂)₃](C₁₀H₇N₄O)(BF₄), (VI). In compound (I), one of the anions is disordered over two sets of atomic sites with equal occupancies while, in the second anion, just one of the C(CN)2 units is disordered, again over two sets of atomic sites with equal occupancies: the anionic components are linked by multiple C - H⋯N hydrogen bonds to form a three-dimensional framework. In compound (II), the polynitrile anion is disordered over two sets of atomic sites with occupancies in the approximate ratio 3:1, while the perchlorate anion is disordered over three sets of atomic sites: there are C - N⋯π interactions between the cations and the polynitrile anion. The polynitrile anion in compound (III) is fully ordered, but the tetrafluoridoborate anion is disordered over two sets of atomic sites with occupancies 0.671 (4) and 0.329 (4): the cations and the tetrafluoridoborate anions are linked by C - H⋯F interactions to form an interrupted chain. Compounds (IV) and (V) are isostructural and all of the ionic components are fully ordered in both of them: the cations and tetrafluoridoborate anions are linked into C₂²(12) chains. The polynitrile anion in compound (VI) is disordered over two sets of atomic sites with approximately equal occupancies, and here the chains formed by the cations and the tetrafluoridoborate anions are of the C₂²(13) type.

Original language	English
Pages (from-to)	1717-1726
Number of pages	10
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	74
Issue number	12
Early online date	6 Nov 2018
DOIs	https://doi.org/10.1107/S2056989018015426
Publication status	Published - Dec 2018

Keywords

C - N⋯π interactions
Crystal structure
Disorder
Hydrogen bonding
Polynitrile anions
Supramolecular assembly
Synthesis
tris(bipyridyl)iron(II) complexes

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Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions (crystallography data)
Addala, A. (Creator), Setifi, Z. (Creator), Morimoto, Y. (Creator), Artetxe, B. (Creator), Matsumoto, T. (Creator), Gutiérrez-Zorrilla, J. M. (Creator) & Glidewell, C. (Creator), Cambridge Crystallographic Data Centre, 31 Oct 2018
https://dx.doi.org/10.5517/ccdc.csd.cc20zmk6 and 5 more links, https://dx.doi.org/10.5517/ccdc.csd.cc20zml7, https://dx.doi.org/10.5517/ccdc.csd.cc20zmm8, https://dx.doi.org/10.5517/ccdc.csd.cc20zmn9, https://dx.doi.org/10.5517/ccdc.csd.cc20zmpb, https://dx.doi.org/10.5517/ccdc.csd.cc20zmqc (show fewer)
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Addala, A., Setifi, Z., Morimoto, Y., Artetxe, B., Matsumoto, T., Gutiérrez-Zorrilla, J. M., & Glidewell, C. (2018). Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions. Acta Crystallographica Section E: Crystallographic Communications , 74(12), 1717-1726. https://doi.org/10.1107/S2056989018015426

Addala, Abderezak ; Setifi, Zouaoui ; Morimoto, Yukio et al. / Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions. In: Acta Crystallographica Section E: Crystallographic Communications . 2018 ; Vol. 74, No. 12. pp. 1717-1726.

@article{5de94ba4a58c40008669ef31e23b8921,

title = "Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions",

abstract = "Structures are reported for six closely related salts of tris(bipyridyl)iron(II) cations, namely tris(2,2′-bipyridine)iron(II) bis(1,1,3,3-tetracyano-2-methoxypropenide) 0.776-hydrate, [Fe(C10H8N2)3](C8H3N4O)2.0.776H2O, (I), tris(2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(propylsulfanyl)propenide perchlorate, [Fe(C10H8N2)3](C10H7N4S)(ClO4), (II), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-methoxypropenide tetrafluoridoborate ethanol 0.926-solvate, [Fe(C12H12N2)3](C8H3N4O)(BF4).0.926C2H2O, (III), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-ethoxypropenide tetrafluoridoborate, [Fe(C12H12N2)3](C9H5N4O)(BF4), (IV), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(ethylsufanyl)propenide tetrafluoridoborate, [Fe(C12H12N2)3](C9H5N4S)(BF4), (V), and tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-propoxypropenide tetrafluoridoborate, [Fe(C12H12N2)3](C10H7N4O)(BF4), (VI). In compound (I), one of the anions is disordered over two sets of atomic sites with equal occupancies while, in the second anion, just one of the C(CN)2 units is disordered, again over two sets of atomic sites with equal occupancies: the anionic components are linked by multiple C - H⋯N hydrogen bonds to form a three-dimensional framework. In compound (II), the polynitrile anion is disordered over two sets of atomic sites with occupancies in the approximate ratio 3:1, while the perchlorate anion is disordered over three sets of atomic sites: there are C - N⋯π interactions between the cations and the polynitrile anion. The polynitrile anion in compound (III) is fully ordered, but the tetrafluoridoborate anion is disordered over two sets of atomic sites with occupancies 0.671 (4) and 0.329 (4): the cations and the tetrafluoridoborate anions are linked by C - H⋯F interactions to form an interrupted chain. Compounds (IV) and (V) are isostructural and all of the ionic components are fully ordered in both of them: the cations and tetrafluoridoborate anions are linked into C22(12) chains. The polynitrile anion in compound (VI) is disordered over two sets of atomic sites with approximately equal occupancies, and here the chains formed by the cations and the tetrafluoridoborate anions are of the C22(13) type.",

keywords = "C - N⋯π interactions, Crystal structure, Disorder, Hydrogen bonding, Polynitrile anions, Supramolecular assembly, Synthesis, tris(bipyridyl)iron(II) complexes",

author = "Abderezak Addala and Zouaoui Setifi and Yukio Morimoto and Ben{\~a}t Artetxe and Takashi Matsumoto and Guti{\'e}rrez-Zorrilla, {Juan M.} and Christopher Glidewell",

note = "ZS gratefully acknowledges the Algerian DGRSDT (Direction G{\'e}n{\'e}rale de la Recherche Scientifique et du D{\'e}veloppement Technologique) and Universit{\'e} Ferhat Abbas S{\'e}tif 1 for financial support.",

year = "2018",

month = dec,

doi = "10.1107/S2056989018015426",

language = "English",

volume = "74",

pages = "1717--1726",

journal = "Acta Crystallographica Section E: Crystallographic Communications ",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "12",

}

Addala, A, Setifi, Z, Morimoto, Y, Artetxe, B, Matsumoto, T, Gutiérrez-Zorrilla, JM & Glidewell, C 2018, 'Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions', Acta Crystallographica Section E: Crystallographic Communications , vol. 74, no. 12, pp. 1717-1726. https://doi.org/10.1107/S2056989018015426

Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions. / Addala, Abderezak; Setifi, Zouaoui; Morimoto, Yukio et al.
In: Acta Crystallographica Section E: Crystallographic Communications , Vol. 74, No. 12, 12.2018, p. 1717-1726.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions

AU - Addala, Abderezak

AU - Setifi, Zouaoui

AU - Morimoto, Yukio

AU - Artetxe, Benãt

AU - Matsumoto, Takashi

AU - Gutiérrez-Zorrilla, Juan M.

AU - Glidewell, Christopher

N1 - ZS gratefully acknowledges the Algerian DGRSDT (Direction Générale de la Recherche Scientifique et du Développement Technologique) and Université Ferhat Abbas Sétif 1 for financial support.

PY - 2018/12

Y1 - 2018/12

N2 - Structures are reported for six closely related salts of tris(bipyridyl)iron(II) cations, namely tris(2,2′-bipyridine)iron(II) bis(1,1,3,3-tetracyano-2-methoxypropenide) 0.776-hydrate, [Fe(C10H8N2)3](C8H3N4O)2.0.776H2O, (I), tris(2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(propylsulfanyl)propenide perchlorate, [Fe(C10H8N2)3](C10H7N4S)(ClO4), (II), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-methoxypropenide tetrafluoridoborate ethanol 0.926-solvate, [Fe(C12H12N2)3](C8H3N4O)(BF4).0.926C2H2O, (III), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-ethoxypropenide tetrafluoridoborate, [Fe(C12H12N2)3](C9H5N4O)(BF4), (IV), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(ethylsufanyl)propenide tetrafluoridoborate, [Fe(C12H12N2)3](C9H5N4S)(BF4), (V), and tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-propoxypropenide tetrafluoridoborate, [Fe(C12H12N2)3](C10H7N4O)(BF4), (VI). In compound (I), one of the anions is disordered over two sets of atomic sites with equal occupancies while, in the second anion, just one of the C(CN)2 units is disordered, again over two sets of atomic sites with equal occupancies: the anionic components are linked by multiple C - H⋯N hydrogen bonds to form a three-dimensional framework. In compound (II), the polynitrile anion is disordered over two sets of atomic sites with occupancies in the approximate ratio 3:1, while the perchlorate anion is disordered over three sets of atomic sites: there are C - N⋯π interactions between the cations and the polynitrile anion. The polynitrile anion in compound (III) is fully ordered, but the tetrafluoridoborate anion is disordered over two sets of atomic sites with occupancies 0.671 (4) and 0.329 (4): the cations and the tetrafluoridoborate anions are linked by C - H⋯F interactions to form an interrupted chain. Compounds (IV) and (V) are isostructural and all of the ionic components are fully ordered in both of them: the cations and tetrafluoridoborate anions are linked into C22(12) chains. The polynitrile anion in compound (VI) is disordered over two sets of atomic sites with approximately equal occupancies, and here the chains formed by the cations and the tetrafluoridoborate anions are of the C22(13) type.

AB - Structures are reported for six closely related salts of tris(bipyridyl)iron(II) cations, namely tris(2,2′-bipyridine)iron(II) bis(1,1,3,3-tetracyano-2-methoxypropenide) 0.776-hydrate, [Fe(C10H8N2)3](C8H3N4O)2.0.776H2O, (I), tris(2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(propylsulfanyl)propenide perchlorate, [Fe(C10H8N2)3](C10H7N4S)(ClO4), (II), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-methoxypropenide tetrafluoridoborate ethanol 0.926-solvate, [Fe(C12H12N2)3](C8H3N4O)(BF4).0.926C2H2O, (III), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-ethoxypropenide tetrafluoridoborate, [Fe(C12H12N2)3](C9H5N4O)(BF4), (IV), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(ethylsufanyl)propenide tetrafluoridoborate, [Fe(C12H12N2)3](C9H5N4S)(BF4), (V), and tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-propoxypropenide tetrafluoridoborate, [Fe(C12H12N2)3](C10H7N4O)(BF4), (VI). In compound (I), one of the anions is disordered over two sets of atomic sites with equal occupancies while, in the second anion, just one of the C(CN)2 units is disordered, again over two sets of atomic sites with equal occupancies: the anionic components are linked by multiple C - H⋯N hydrogen bonds to form a three-dimensional framework. In compound (II), the polynitrile anion is disordered over two sets of atomic sites with occupancies in the approximate ratio 3:1, while the perchlorate anion is disordered over three sets of atomic sites: there are C - N⋯π interactions between the cations and the polynitrile anion. The polynitrile anion in compound (III) is fully ordered, but the tetrafluoridoborate anion is disordered over two sets of atomic sites with occupancies 0.671 (4) and 0.329 (4): the cations and the tetrafluoridoborate anions are linked by C - H⋯F interactions to form an interrupted chain. Compounds (IV) and (V) are isostructural and all of the ionic components are fully ordered in both of them: the cations and tetrafluoridoborate anions are linked into C22(12) chains. The polynitrile anion in compound (VI) is disordered over two sets of atomic sites with approximately equal occupancies, and here the chains formed by the cations and the tetrafluoridoborate anions are of the C22(13) type.

KW - C - N⋯π interactions

KW - Crystal structure

KW - Disorder

KW - Hydrogen bonding

KW - Polynitrile anions

KW - Supramolecular assembly

KW - Synthesis

KW - tris(bipyridyl)iron(II) complexes

U2 - 10.1107/S2056989018015426

DO - 10.1107/S2056989018015426

M3 - Article

AN - SCOPUS:85058044189

SN - 2056-9890

VL - 74

SP - 1717

EP - 1726

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

IS - 12

ER -

Addala A, Setifi Z, Morimoto Y, Artetxe B, Matsumoto T, Gutiérrez-Zorrilla JM et al. Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions. Acta Crystallographica Section E: Crystallographic Communications . 2018 Dec;74(12):1717-1726. Epub 2018 Nov 6. doi: 10.1107/S2056989018015426

Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions

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Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C - N⋯π interactions (crystallography data)

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