Crystal structures of four co-crystals of (E)-1,2-di(pyridin-4-yl)ethene with 4-alkoxybenzoic acids

4-methoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1), 4-ethoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1), 4-n-propoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1) and 4-n-butoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1)

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Abstract

The crystal structures of four hydrogen-bonded co-crystals of 4-alkoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1), namely, 2C8H8O3·C12H10N2, (I), 2C9H10O3·C12H10N2, (II), 2C10H12O3·C12H10N2, (III) and 2C11H14O3·C12H10N2, (IV), have been determined at 93 K. In compounds (I) and (IV), the asymmetric units are each composed of one 4-alkoxybenzoic acid molecule and one half-molecule of (E)-1,2-di(pyridin-4-yl)ethene, which lies on an inversion centre. The asymmetric unit of (II) consists of two crystallographically independent 4-ethoxybenzoic acid molecules and one 1,2-di(pyridin-4-yl)ethene molecule. Compound (III) crystallizes in a non-centrosymmetric space group (Pc) and the asymmetric unit comprises four 4-n-propoxybenzoic acid molecules and two (E)-1,2-di(pyridin-4-yl)ethane molecules. In each crystal, the acid and base components are linked by O - H⋯N hydrogen bonds, forming a linear hydrogen-bonded 2:1 unit of the acid and the base. In (I), (II) and (III), intermolecular C - H⋯O interactions are observed. The 2:1 units of (I) and (II) are linked via C - H⋯O hydrogen bonds, forming tape structures. In (III), the C - H⋯O hydrogen bonds, except for those formed in the units, link the two crystallographically independent 2:1 units. In (IV), no C - H⋯O interactions are observed, but π-π and C - H⋯π interactions link the units into a column structure.

Original languageEnglish
Pages (from-to)1666-1671
Number of pages6
JournalActa Crystallographica Section E: Crystallographic Communications
Volume72
DOIs
Publication statusPublished - 2016

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Crystal structure
Crystals
acids
crystal structure
Molecules
Acids
crystals
molecules
Hydrogen bonds
hydrogen bonds
Hydrogen
Ethane
interactions
hydrogen
ethane
Tapes
tapes
ethylene
ethoxybenzoic acid
inversions

Keywords

  • (E)-1,2-di(pyridin-4-yl)ethene
  • 4-alkoxybenzoic acid
  • crystal structure
  • hydrogen-bonded liquid crystal

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

@article{747c892913884596b22ca16e0fa1d4ba,
title = "Crystal structures of four co-crystals of (E)-1,2-di(pyridin-4-yl)ethene with 4-alkoxybenzoic acids: 4-methoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1), 4-ethoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1), 4-n-propoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1) and 4-n-butoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1)",
abstract = "The crystal structures of four hydrogen-bonded co-crystals of 4-alkoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1), namely, 2C8H8O3·C12H10N2, (I), 2C9H10O3·C12H10N2, (II), 2C10H12O3·C12H10N2, (III) and 2C11H14O3·C12H10N2, (IV), have been determined at 93 K. In compounds (I) and (IV), the asymmetric units are each composed of one 4-alkoxybenzoic acid molecule and one half-molecule of (E)-1,2-di(pyridin-4-yl)ethene, which lies on an inversion centre. The asymmetric unit of (II) consists of two crystallographically independent 4-ethoxybenzoic acid molecules and one 1,2-di(pyridin-4-yl)ethene molecule. Compound (III) crystallizes in a non-centrosymmetric space group (Pc) and the asymmetric unit comprises four 4-n-propoxybenzoic acid molecules and two (E)-1,2-di(pyridin-4-yl)ethane molecules. In each crystal, the acid and base components are linked by O - H⋯N hydrogen bonds, forming a linear hydrogen-bonded 2:1 unit of the acid and the base. In (I), (II) and (III), intermolecular C - H⋯O interactions are observed. The 2:1 units of (I) and (II) are linked via C - H⋯O hydrogen bonds, forming tape structures. In (III), the C - H⋯O hydrogen bonds, except for those formed in the units, link the two crystallographically independent 2:1 units. In (IV), no C - H⋯O interactions are observed, but π-π and C - H⋯π interactions link the units into a column structure.",
keywords = "(E)-1,2-di(pyridin-4-yl)ethene, 4-alkoxybenzoic acid, crystal structure, hydrogen-bonded liquid crystal",
author = "Yohei Tabuchi and Kazuma Gotoh and Hiroyuki Ishida",
year = "2016",
doi = "10.1107/S2056989016017138",
language = "English",
volume = "72",
pages = "1666--1671",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Crystal structures of four co-crystals of (E)-1,2-di(pyridin-4-yl)ethene with 4-alkoxybenzoic acids

T2 - 4-methoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1), 4-ethoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1), 4-n-propoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1) and 4-n-butoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1)

AU - Tabuchi, Yohei

AU - Gotoh, Kazuma

AU - Ishida, Hiroyuki

PY - 2016

Y1 - 2016

N2 - The crystal structures of four hydrogen-bonded co-crystals of 4-alkoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1), namely, 2C8H8O3·C12H10N2, (I), 2C9H10O3·C12H10N2, (II), 2C10H12O3·C12H10N2, (III) and 2C11H14O3·C12H10N2, (IV), have been determined at 93 K. In compounds (I) and (IV), the asymmetric units are each composed of one 4-alkoxybenzoic acid molecule and one half-molecule of (E)-1,2-di(pyridin-4-yl)ethene, which lies on an inversion centre. The asymmetric unit of (II) consists of two crystallographically independent 4-ethoxybenzoic acid molecules and one 1,2-di(pyridin-4-yl)ethene molecule. Compound (III) crystallizes in a non-centrosymmetric space group (Pc) and the asymmetric unit comprises four 4-n-propoxybenzoic acid molecules and two (E)-1,2-di(pyridin-4-yl)ethane molecules. In each crystal, the acid and base components are linked by O - H⋯N hydrogen bonds, forming a linear hydrogen-bonded 2:1 unit of the acid and the base. In (I), (II) and (III), intermolecular C - H⋯O interactions are observed. The 2:1 units of (I) and (II) are linked via C - H⋯O hydrogen bonds, forming tape structures. In (III), the C - H⋯O hydrogen bonds, except for those formed in the units, link the two crystallographically independent 2:1 units. In (IV), no C - H⋯O interactions are observed, but π-π and C - H⋯π interactions link the units into a column structure.

AB - The crystal structures of four hydrogen-bonded co-crystals of 4-alkoxybenzoic acid-(E)-1,2-di(pyridin-4-yl)ethene (2/1), namely, 2C8H8O3·C12H10N2, (I), 2C9H10O3·C12H10N2, (II), 2C10H12O3·C12H10N2, (III) and 2C11H14O3·C12H10N2, (IV), have been determined at 93 K. In compounds (I) and (IV), the asymmetric units are each composed of one 4-alkoxybenzoic acid molecule and one half-molecule of (E)-1,2-di(pyridin-4-yl)ethene, which lies on an inversion centre. The asymmetric unit of (II) consists of two crystallographically independent 4-ethoxybenzoic acid molecules and one 1,2-di(pyridin-4-yl)ethene molecule. Compound (III) crystallizes in a non-centrosymmetric space group (Pc) and the asymmetric unit comprises four 4-n-propoxybenzoic acid molecules and two (E)-1,2-di(pyridin-4-yl)ethane molecules. In each crystal, the acid and base components are linked by O - H⋯N hydrogen bonds, forming a linear hydrogen-bonded 2:1 unit of the acid and the base. In (I), (II) and (III), intermolecular C - H⋯O interactions are observed. The 2:1 units of (I) and (II) are linked via C - H⋯O hydrogen bonds, forming tape structures. In (III), the C - H⋯O hydrogen bonds, except for those formed in the units, link the two crystallographically independent 2:1 units. In (IV), no C - H⋯O interactions are observed, but π-π and C - H⋯π interactions link the units into a column structure.

KW - (E)-1,2-di(pyridin-4-yl)ethene

KW - 4-alkoxybenzoic acid

KW - crystal structure

KW - hydrogen-bonded liquid crystal

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U2 - 10.1107/S2056989016017138

DO - 10.1107/S2056989016017138

M3 - Article

VL - 72

SP - 1666

EP - 1671

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

ER -