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

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

Research output: Contribution to journalArticleScientificpeer-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 languageEnglish
Pages (from-to)o765-o766
JournalActa Crystallographica Section E: Structure Reports Online
VolumeE64
Issue number4
DOIs
Publication statusPublished - 2008
MoE publication typeA1 Journal article-refereed

Fingerprint

Thiophenes
Acetylene
Thiophene
thiophenes
Molecules
Dihedral angle
Benzene
Dimers
dihedral angle
molecules
rings
Hydrogen bonds
benzene
dimers
hydrogen bonds
Hydrogen
spacing
solid state
Atoms
optimization

Keywords

  • organic compounds
  • nanoelectronics
  • optoelectronics
  • molecular electronics

Cite this

Figueira, João ; Vertlib, Viatslav ; Rodrigues, João ; Nättinen, Kalle ; Rissanen, Kari. / 4,4'-[Thiophene-2,5-diylbis(ethyne-2,1-diyl)]dibenzonitrile. In: Acta Crystallographica Section E: Structure Reports Online. 2008 ; Vol. E64, No. 4. pp. o765-o766.
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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",
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Figueira, J, Vertlib, V, Rodrigues, J, Nättinen, K & Rissanen, K 2008, '4,4'-[Thiophene-2,5-diylbis(ethyne-2,1-diyl)]dibenzonitrile', Acta Crystallographica Section E: Structure Reports Online, vol. E64, no. 4, pp. o765-o766. https://doi.org/10.1107/S1600536808008106

4,4'-[Thiophene-2,5-diylbis(ethyne-2,1-diyl)]dibenzonitrile. / Figueira, João; Vertlib, Viatslav; Rodrigues, João; Nättinen, Kalle; Rissanen, Kari.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. E64, No. 4, 2008, p. o765-o766.

Research output: Contribution to journalArticleScientificpeer-review

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

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SP - o765-o766

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

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