Crystal structures of hydrogen-bonded co-crystals as liquid crystal precursors: 4-(n-pentyloxy)benzoic acid-(E)-1,2-bis(pyridin-4-yl)ethene (2/1) and 4-(n-hexyloxy)benzoic acid-(E)-1,2-bis(pyridin-4-yl)ethene (2/1)

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Abstract

The crystal structures of title hydrogen-bonded co-crystals, 2C12H16O3 C12H10N2, (I), and 2C13H18O3 C12H10N2, (II), have been determined at 93K. In (I), the asymmetric unit consists of one 4-(n-pentyloxy)benzoic acid molecule and one half-molecule of (E)-1,2-bis(pyridin-4-yl)ethene, which lies about an inversion centre. The asymmetric unit of (II) comprises two crystallographically independent 4-(n-hexyloxy)benzoic acid molecules and one 1,2-bis(pyridin-4-yl)ethene molecule. 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. The 2:1 units are linked via C - H⋯π and π-π interactions [centroid-centroid distances of 3.661(2) and 3.909(2)Å for (I), and 3.546(2)-3.725(4)Å for (II)], forming column structures. In (II), the base molecule is orientationally disordered over two sets of sites approximately around the N⋯N molecular axis, with an occupancy ratio of 0.647(4):0.353(4), and the average structure of the 2:1 unit adopts nearly pseudo-C 2 symmetry. Both compounds show liquid-crystal behaviour.

Original languageEnglish
Pages (from-to)1771-1775
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
Volume72
DOIs
Publication statusPublished - 2016

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Liquid Crystals
Benzoic Acid
Benzoic acid
benzoic acid
Liquid crystals
Hydrogen
Crystal structure
liquid crystals
Crystals
crystal structure
Molecules
hydrogen
crystals
molecules
centroids
acids
Acids
Crystal symmetry
Hydrogen bonds
ethylene

Keywords

  • (E)-1,2-bis(pyridin-4-yl)ethene
  • 4-(n-hexyloxy)benzoic acid hydrogen-bonded liquid crystal
  • 4-(n-pentyloxy)benzoic acid
  • crystal structure

ASJC Scopus subject areas

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

Cite this

@article{4d03330b14034eae809bccd477000c1d,
title = "Crystal structures of hydrogen-bonded co-crystals as liquid crystal precursors: 4-(n-pentyloxy)benzoic acid-(E)-1,2-bis(pyridin-4-yl)ethene (2/1) and 4-(n-hexyloxy)benzoic acid-(E)-1,2-bis(pyridin-4-yl)ethene (2/1)",
abstract = "The crystal structures of title hydrogen-bonded co-crystals, 2C12H16O3 C12H10N2, (I), and 2C13H18O3 C12H10N2, (II), have been determined at 93K. In (I), the asymmetric unit consists of one 4-(n-pentyloxy)benzoic acid molecule and one half-molecule of (E)-1,2-bis(pyridin-4-yl)ethene, which lies about an inversion centre. The asymmetric unit of (II) comprises two crystallographically independent 4-(n-hexyloxy)benzoic acid molecules and one 1,2-bis(pyridin-4-yl)ethene molecule. 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. The 2:1 units are linked via C - H⋯π and π-π interactions [centroid-centroid distances of 3.661(2) and 3.909(2){\AA} for (I), and 3.546(2)-3.725(4){\AA} for (II)], forming column structures. In (II), the base molecule is orientationally disordered over two sets of sites approximately around the N⋯N molecular axis, with an occupancy ratio of 0.647(4):0.353(4), and the average structure of the 2:1 unit adopts nearly pseudo-C 2 symmetry. Both compounds show liquid-crystal behaviour.",
keywords = "(E)-1,2-bis(pyridin-4-yl)ethene, 4-(n-hexyloxy)benzoic acid hydrogen-bonded liquid crystal, 4-(n-pentyloxy)benzoic acid, crystal structure",
author = "Yohei Tabuchi and Kazuma Gotoh and Hiroyuki Ishida",
year = "2016",
doi = "10.1107/S2056989016017655",
language = "English",
volume = "72",
pages = "1771--1775",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Crystal structures of hydrogen-bonded co-crystals as liquid crystal precursors

T2 - 4-(n-pentyloxy)benzoic acid-(E)-1,2-bis(pyridin-4-yl)ethene (2/1) and 4-(n-hexyloxy)benzoic acid-(E)-1,2-bis(pyridin-4-yl)ethene (2/1)

AU - Tabuchi, Yohei

AU - Gotoh, Kazuma

AU - Ishida, Hiroyuki

PY - 2016

Y1 - 2016

N2 - The crystal structures of title hydrogen-bonded co-crystals, 2C12H16O3 C12H10N2, (I), and 2C13H18O3 C12H10N2, (II), have been determined at 93K. In (I), the asymmetric unit consists of one 4-(n-pentyloxy)benzoic acid molecule and one half-molecule of (E)-1,2-bis(pyridin-4-yl)ethene, which lies about an inversion centre. The asymmetric unit of (II) comprises two crystallographically independent 4-(n-hexyloxy)benzoic acid molecules and one 1,2-bis(pyridin-4-yl)ethene molecule. 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. The 2:1 units are linked via C - H⋯π and π-π interactions [centroid-centroid distances of 3.661(2) and 3.909(2)Å for (I), and 3.546(2)-3.725(4)Å for (II)], forming column structures. In (II), the base molecule is orientationally disordered over two sets of sites approximately around the N⋯N molecular axis, with an occupancy ratio of 0.647(4):0.353(4), and the average structure of the 2:1 unit adopts nearly pseudo-C 2 symmetry. Both compounds show liquid-crystal behaviour.

AB - The crystal structures of title hydrogen-bonded co-crystals, 2C12H16O3 C12H10N2, (I), and 2C13H18O3 C12H10N2, (II), have been determined at 93K. In (I), the asymmetric unit consists of one 4-(n-pentyloxy)benzoic acid molecule and one half-molecule of (E)-1,2-bis(pyridin-4-yl)ethene, which lies about an inversion centre. The asymmetric unit of (II) comprises two crystallographically independent 4-(n-hexyloxy)benzoic acid molecules and one 1,2-bis(pyridin-4-yl)ethene molecule. 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. The 2:1 units are linked via C - H⋯π and π-π interactions [centroid-centroid distances of 3.661(2) and 3.909(2)Å for (I), and 3.546(2)-3.725(4)Å for (II)], forming column structures. In (II), the base molecule is orientationally disordered over two sets of sites approximately around the N⋯N molecular axis, with an occupancy ratio of 0.647(4):0.353(4), and the average structure of the 2:1 unit adopts nearly pseudo-C 2 symmetry. Both compounds show liquid-crystal behaviour.

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

KW - 4-(n-hexyloxy)benzoic acid hydrogen-bonded liquid crystal

KW - 4-(n-pentyloxy)benzoic acid

KW - crystal structure

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U2 - 10.1107/S2056989016017655

DO - 10.1107/S2056989016017655

M3 - Article

AN - SCOPUS:85003671300

VL - 72

SP - 1771

EP - 1775

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

ER -