Crystal structures of three co-crystals of 4,4′-bipyridyl with 4-alkoxybenzoic acids

4-ethoxybenzoic acid-4,4′-bipyridyl (2/1), 4-n-propoxybenzoic acid-4,4′-bipyridyl (2/1) and 4-n-butoxybenzoic acid-4,4′-bipyridyl (2/1)

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Abstract

The crystal structures of three hydrogen-bonded co-crystals of 4-alkoxybenzoic acid-4,4′-bipyridyl (2/1), namely, 2C9H10O3·C10H8N2, (I), 2C10H12O3·C10H8N2, (II) and 2C11H14O3·C10H8N2, (III), have been determined at 93 K. Although the structure of (I) has been determined in the space group P21 with Z = 4 [Lai et al. (2008). J. Struct. Chem. 49, 1137-1140], the present study shows that the space group is P21/n with Z = 4. In each crystal, the 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 unit of (I) adopts nearly pseudo-C 2 symmetry, viz. twofold rotation around an axis passing through the mid-point of the central C - C bond of 4,4′-bipyridyl, while the units of (II) and (III), except for the terminal alkyl chains, have pseudo-inversion symmetry. The 2:1 units of (I), (II) and (III) are linked via C - H⋯O hydrogen bonds, forming sheet, double-tape and tape structures, respectively.

Original languageEnglish
Pages (from-to)1290-1295
Number of pages6
JournalActa Crystallographica Section E: Crystallographic Communications
Volume71
DOIs
Publication statusPublished - 2015

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2,2'-Dipyridyl
Tapes
tapes
Hydrogen
Hydrogen bonds
Crystal structure
hydrogen bonds
Crystals
acids
crystal structure
Acids
symmetry
hydrogen
crystals
inversions
ethoxybenzoic acid

Keywords

  • 4,4′-bipyridyl
  • 4-alkoxybenzoic acid
  • crystal structure
  • hydrogen-bonded liquid crystal

ASJC Scopus subject areas

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

Cite this

@article{b42518ab852b4bc1b4269cb3cf0f3895,
title = "Crystal structures of three co-crystals of 4,4′-bipyridyl with 4-alkoxybenzoic acids: 4-ethoxybenzoic acid-4,4′-bipyridyl (2/1), 4-n-propoxybenzoic acid-4,4′-bipyridyl (2/1) and 4-n-butoxybenzoic acid-4,4′-bipyridyl (2/1)",
abstract = "The crystal structures of three hydrogen-bonded co-crystals of 4-alkoxybenzoic acid-4,4′-bipyridyl (2/1), namely, 2C9H10O3·C10H8N2, (I), 2C10H12O3·C10H8N2, (II) and 2C11H14O3·C10H8N2, (III), have been determined at 93 K. Although the structure of (I) has been determined in the space group P21 with Z = 4 [Lai et al. (2008). J. Struct. Chem. 49, 1137-1140], the present study shows that the space group is P21/n with Z = 4. In each crystal, the 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 unit of (I) adopts nearly pseudo-C 2 symmetry, viz. twofold rotation around an axis passing through the mid-point of the central C - C bond of 4,4′-bipyridyl, while the units of (II) and (III), except for the terminal alkyl chains, have pseudo-inversion symmetry. The 2:1 units of (I), (II) and (III) are linked via C - H⋯O hydrogen bonds, forming sheet, double-tape and tape structures, respectively.",
keywords = "4,4′-bipyridyl, 4-alkoxybenzoic acid, crystal structure, hydrogen-bonded liquid crystal",
author = "Yohei Tabuchi and Kazuma Gotoh and Hiroyuki Ishida",
year = "2015",
doi = "10.1107/S2056989015018435",
language = "English",
volume = "71",
pages = "1290--1295",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Crystal structures of three co-crystals of 4,4′-bipyridyl with 4-alkoxybenzoic acids

T2 - 4-ethoxybenzoic acid-4,4′-bipyridyl (2/1), 4-n-propoxybenzoic acid-4,4′-bipyridyl (2/1) and 4-n-butoxybenzoic acid-4,4′-bipyridyl (2/1)

AU - Tabuchi, Yohei

AU - Gotoh, Kazuma

AU - Ishida, Hiroyuki

PY - 2015

Y1 - 2015

N2 - The crystal structures of three hydrogen-bonded co-crystals of 4-alkoxybenzoic acid-4,4′-bipyridyl (2/1), namely, 2C9H10O3·C10H8N2, (I), 2C10H12O3·C10H8N2, (II) and 2C11H14O3·C10H8N2, (III), have been determined at 93 K. Although the structure of (I) has been determined in the space group P21 with Z = 4 [Lai et al. (2008). J. Struct. Chem. 49, 1137-1140], the present study shows that the space group is P21/n with Z = 4. In each crystal, the 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 unit of (I) adopts nearly pseudo-C 2 symmetry, viz. twofold rotation around an axis passing through the mid-point of the central C - C bond of 4,4′-bipyridyl, while the units of (II) and (III), except for the terminal alkyl chains, have pseudo-inversion symmetry. The 2:1 units of (I), (II) and (III) are linked via C - H⋯O hydrogen bonds, forming sheet, double-tape and tape structures, respectively.

AB - The crystal structures of three hydrogen-bonded co-crystals of 4-alkoxybenzoic acid-4,4′-bipyridyl (2/1), namely, 2C9H10O3·C10H8N2, (I), 2C10H12O3·C10H8N2, (II) and 2C11H14O3·C10H8N2, (III), have been determined at 93 K. Although the structure of (I) has been determined in the space group P21 with Z = 4 [Lai et al. (2008). J. Struct. Chem. 49, 1137-1140], the present study shows that the space group is P21/n with Z = 4. In each crystal, the 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 unit of (I) adopts nearly pseudo-C 2 symmetry, viz. twofold rotation around an axis passing through the mid-point of the central C - C bond of 4,4′-bipyridyl, while the units of (II) and (III), except for the terminal alkyl chains, have pseudo-inversion symmetry. The 2:1 units of (I), (II) and (III) are linked via C - H⋯O hydrogen bonds, forming sheet, double-tape and tape structures, respectively.

KW - 4,4′-bipyridyl

KW - 4-alkoxybenzoic acid

KW - crystal structure

KW - hydrogen-bonded liquid crystal

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U2 - 10.1107/S2056989015018435

DO - 10.1107/S2056989015018435

M3 - Article

VL - 71

SP - 1290

EP - 1295

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

ER -