4,4'-[Thiophene-2,5-diylbis(ethyne-2,1-diyl)]dibenzonitrile

João Figueira; Viatslav Vertlib; João Rodrigues; Kalle Nättinen; Kari Rissanen

doi:10.1107/S1600536808008106

4,4'-[Thiophene-2,5-diylbis(ethyne-2,1-diyl)]dibenzonitrile

João Figueira, Viatslav Vertlib, João Rodrigues, Kalle Nättinen, Kari Rissanen

VTT Technical Research Centre of Finland

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

Abstract

In the solid state, the title compound, C22H10N2S, forms centrosymmetric dimers by pairs of non-classical C-H...S hydrogen bonds linking approximately coplanar molecules. The benzene ring involved in this interaction makes a dihedral angle of only 7.21 (16)° with the thiophene ring, while the other benzene ring is twisted somewhat out of the plane, with a dihedral angle of 39.58 (9)°. The hydrogen-bonded dimers stack on top of each other with an interplanar spacing of 3.44 Å. C-H...N hydrogen bonds link together stacks that run in approximately perpendicular directions. Each molecule thus interacts with 12 adjacent molecules, five of them approaching closer than the sum of the van der Waals radii for the relevant atoms. Optimization of the inter-stack contacts contributes to the non-planarity of the molecule.

Original language	English
Pages (from-to)	o765-o766
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	E64
Issue number	4
DOIs	https://doi.org/10.1107/S1600536808008106
Publication status	Published - 2008
MoE publication type	A1 Journal article-refereed

Keywords

organic compounds
nanoelectronics
optoelectronics
molecular electronics

Access to Document

10.1107/S1600536808008106

Cite this

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title = "4,4'-[Thiophene-2,5-diylbis(ethyne-2,1-diyl)]dibenzonitrile",

abstract = "In the solid state, the title compound, C22H10N2S, forms centrosymmetric dimers by pairs of non-classical C-H...S hydrogen bonds linking approximately coplanar molecules. The benzene ring involved in this interaction makes a dihedral angle of only 7.21 (16)° with the thiophene ring, while the other benzene ring is twisted somewhat out of the plane, with a dihedral angle of 39.58 (9)°. The hydrogen-bonded dimers stack on top of each other with an interplanar spacing of 3.44 {\AA}. C-H...N hydrogen bonds link together stacks that run in approximately perpendicular directions. Each molecule thus interacts with 12 adjacent molecules, five of them approaching closer than the sum of the van der Waals radii for the relevant atoms. Optimization of the inter-stack contacts contributes to the non-planarity of the molecule.",

keywords = "organic compounds, nanoelectronics, optoelectronics, molecular electronics",

author = "Jo{\~a}o Figueira and Viatslav Vertlib and Jo{\~a}o Rodrigues and Kalle N{\"a}ttinen and Kari Rissanen",

year = "2008",

doi = "10.1107/S1600536808008106",

language = "English",

volume = "E64",

pages = "o765--o766",

journal = "Acta Crystallographica Section E: Structure Reports Online",

issn = "1600-5368",

publisher = "Elsevier",

number = "4",

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TY - JOUR

T1 - 4,4'-[Thiophene-2,5-diylbis(ethyne-2,1-diyl)]dibenzonitrile

AU - Figueira, João

AU - Vertlib, Viatslav

AU - Rodrigues, João

AU - Nättinen, Kalle

AU - Rissanen, Kari

PY - 2008

Y1 - 2008

N2 - In the solid state, the title compound, C22H10N2S, forms centrosymmetric dimers by pairs of non-classical C-H...S hydrogen bonds linking approximately coplanar molecules. The benzene ring involved in this interaction makes a dihedral angle of only 7.21 (16)° with the thiophene ring, while the other benzene ring is twisted somewhat out of the plane, with a dihedral angle of 39.58 (9)°. The hydrogen-bonded dimers stack on top of each other with an interplanar spacing of 3.44 Å. C-H...N hydrogen bonds link together stacks that run in approximately perpendicular directions. Each molecule thus interacts with 12 adjacent molecules, five of them approaching closer than the sum of the van der Waals radii for the relevant atoms. Optimization of the inter-stack contacts contributes to the non-planarity of the molecule.

AB - In the solid state, the title compound, C22H10N2S, forms centrosymmetric dimers by pairs of non-classical C-H...S hydrogen bonds linking approximately coplanar molecules. The benzene ring involved in this interaction makes a dihedral angle of only 7.21 (16)° with the thiophene ring, while the other benzene ring is twisted somewhat out of the plane, with a dihedral angle of 39.58 (9)°. The hydrogen-bonded dimers stack on top of each other with an interplanar spacing of 3.44 Å. C-H...N hydrogen bonds link together stacks that run in approximately perpendicular directions. Each molecule thus interacts with 12 adjacent molecules, five of them approaching closer than the sum of the van der Waals radii for the relevant atoms. Optimization of the inter-stack contacts contributes to the non-planarity of the molecule.

KW - organic compounds

KW - nanoelectronics

KW - optoelectronics

KW - molecular electronics

U2 - 10.1107/S1600536808008106

DO - 10.1107/S1600536808008106

M3 - Article

SN - 1600-5368

VL - E64

SP - o765-o766

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 4

ER -

4,4'-[Thiophene-2,5-diylbis(ethyne-2,1-diyl)]dibenzonitrile

Abstract

Keywords

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