1,1'-Diethyl-4,4'-bipyridine-1,1'-diium bis(1,1,3,3-tetracyano-2- ethoxypropenide): multiple C-H⋯N hydrogen bonds form a complex sheet structure

Z. Setifi; F. Lehchili; F. Setifi; A. Beghidja; S.W. Ng; C. Glidewell

doi:10.1107/S2053229614004379

1,1'-Diethyl-4,4'-bipyridine-1,1'-diium bis(1,1,3,3-tetracyano-2- ethoxypropenide): multiple C-H⋯N hydrogen bonds form a complex sheet structure

Z. Setifi, F. Lehchili, F. Setifi, A. Beghidja, S.W. Ng, C. Glidewell

School of Chemistry

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

23 Citations (Scopus)

4 Downloads (Pure)

Abstract

In the title salt, C₁₄H₁₈N₂²⁺·2C₉H₅N₄O⁻, the 1,1′-diethyl-4,4′-bipyridine-1,1′-diium dication lies across a centre of inversion in the space group P2₁/c. In the 1,1,3,3-tetracyano-2-ethoxypropenide anion, the two independent –C(CN)₂ units are rotated, in conrotatory fashion, out of the plane of the central propenide unit, making dihedral angles with the central unit of 16.0 (2) and 23.0 (2)°. The ionic components are linked by C—H⋯N hydrogen bonds to form a complex sheet structure, within which each cation acts as a sixfold donor of hydrogen bonds and each anion acts as a threefold acceptor of hydrogen bonds.

Original language	English
Pages (from-to)	338-341
Number of pages	4
Journal	Acta Crystallographica Section C: Crystal Structure Communications
Volume	70
Issue number	3
DOIs	https://doi.org/10.1107/S2053229614004379
Publication status	Published - 1 Mar 2014

Keywords

Crystal structure
Hydrogen-bonded sheets
Polynitrile anions
4,4′-bipyridine-1,1′-diium
1,1,3,3-tetracyano-2-ethoxypropenide

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10.1107/S2053229614004379

Glidewell_2014_OC_11Diethyl
Copyright 2014 International Union of Crystallography
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title = "1,1'-Diethyl-4,4'-bipyridine-1,1'-diium bis(1,1,3,3-tetracyano-2- ethoxypropenide): multiple C-H⋯N hydrogen bonds form a complex sheet structure",

abstract = "In the title salt, C14H18N22+·2C9H5N4O−, the 1,1′-diethyl-4,4′-bipyridine-1,1′-diium dication lies across a centre of inversion in the space group P21/c. In the 1,1,3,3-tetracyano-2-ethoxypropenide anion, the two independent –C(CN)2 units are rotated, in conrotatory fashion, out of the plane of the central propenide unit, making dihedral angles with the central unit of 16.0 (2) and 23.0 (2)°. The ionic components are linked by C—H⋯N hydrogen bonds to form a complex sheet structure, within which each cation acts as a sixfold donor of hydrogen bonds and each anion acts as a threefold acceptor of hydrogen bonds.",

keywords = "Crystal structure, Hydrogen-bonded sheets, Polynitrile anions, 4,4′-bipyridine-1,1′-diium, 1,1,3,3-tetracyano-2-ethoxypropenide",

author = "Z. Setifi and F. Lehchili and F. Setifi and A. Beghidja and S.W. Ng and C. Glidewell",

note = "The authors acknowledge the Algerian ATRST (Agence The´matique de Recherche en Sciences et Technologie; PNR project) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR-MOHE/SC/03) for financial support.",

year = "2014",

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day = "1",

doi = "10.1107/S2053229614004379",

language = "English",

volume = "70",

pages = "338--341",

journal = "Acta Crystallographica Section C: Crystal Structure Communications",

issn = "0108-2701",

publisher = "International Union of Crystallography",

number = "3",

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1,1'-Diethyl-4,4'-bipyridine-1,1'-diium bis(1,1,3,3-tetracyano-2- ethoxypropenide): multiple C-H⋯N hydrogen bonds form a complex sheet structure. / Setifi, Z.; Lehchili, F.; Setifi, F. et al.
In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 70, No. 3, 01.03.2014, p. 338-341.

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

TY - JOUR

T1 - 1,1'-Diethyl-4,4'-bipyridine-1,1'-diium bis(1,1,3,3-tetracyano-2- ethoxypropenide)

T2 - multiple C-H⋯N hydrogen bonds form a complex sheet structure

AU - Setifi, Z.

AU - Lehchili, F.

AU - Setifi, F.

AU - Beghidja, A.

AU - Ng, S.W.

AU - Glidewell, C.

N1 - The authors acknowledge the Algerian ATRST (Agence The´matique de Recherche en Sciences et Technologie; PNR project) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR-MOHE/SC/03) for financial support.

PY - 2014/3/1

Y1 - 2014/3/1

N2 - In the title salt, C14H18N22+·2C9H5N4O−, the 1,1′-diethyl-4,4′-bipyridine-1,1′-diium dication lies across a centre of inversion in the space group P21/c. In the 1,1,3,3-tetracyano-2-ethoxypropenide anion, the two independent –C(CN)2 units are rotated, in conrotatory fashion, out of the plane of the central propenide unit, making dihedral angles with the central unit of 16.0 (2) and 23.0 (2)°. The ionic components are linked by C—H⋯N hydrogen bonds to form a complex sheet structure, within which each cation acts as a sixfold donor of hydrogen bonds and each anion acts as a threefold acceptor of hydrogen bonds.

AB - In the title salt, C14H18N22+·2C9H5N4O−, the 1,1′-diethyl-4,4′-bipyridine-1,1′-diium dication lies across a centre of inversion in the space group P21/c. In the 1,1,3,3-tetracyano-2-ethoxypropenide anion, the two independent –C(CN)2 units are rotated, in conrotatory fashion, out of the plane of the central propenide unit, making dihedral angles with the central unit of 16.0 (2) and 23.0 (2)°. The ionic components are linked by C—H⋯N hydrogen bonds to form a complex sheet structure, within which each cation acts as a sixfold donor of hydrogen bonds and each anion acts as a threefold acceptor of hydrogen bonds.

KW - Crystal structure

KW - Hydrogen-bonded sheets

KW - Polynitrile anions

KW - 4,4′-bipyridine-1,1′-diium

KW - 1,1,3,3-tetracyano-2-ethoxypropenide

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U2 - 10.1107/S2053229614004379

DO - 10.1107/S2053229614004379

M3 - Article

AN - SCOPUS:84904855069

SN - 0108-2701

VL - 70

SP - 338

EP - 341

JO - Acta Crystallographica Section C: Crystal Structure Communications

JF - Acta Crystallographica Section C: Crystal Structure Communications

IS - 3

ER -

1,1'-Diethyl-4,4'-bipyridine-1,1'-diium bis(1,1,3,3-tetracyano-2- ethoxypropenide): multiple C-H⋯N hydrogen bonds form a complex sheet structure

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