Phenyl-ring rotational disorder in the two-dimensional hydrogen-bonded structure of the 1:1 proton-transfer salt of the diazo-dye precursor 4-(phenyl-diazenyl)aniline (aniline yellow) with l-tartaric acid

Graham Smith, Urs D. Wermuth, David J. Young

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Abstract

In the structure of the 1:1 proton-transfer compound from the reaction of l-tartaric acid with the azo-dye precursor aniline yellow [4-(phenyl - diazenyl)aniline], namely 4-(phenyl-di-az-enyl)-anilinium (2R,3R)-3-carb-oxy-2, 3-dihy-droxy-propano-ate, C12H12N3 +·C4H5O6 -, the asymmetric unit contains two independent 4-(phenyl-diazenyl)-anilinium cations and two hydrogen l-tartrate anions. The structure is unusual in that all four phenyl rings of the two cations have identical rotational disorder with equal occupancy of the conformations. The two hydrogen l-tartrate anions form independent but similar chains through head-to-tail carboxyl-carboxyl-ate O - H⋯O hydrogen bonds [graph set C(7)], which are then extended into a two-dimensional hydrogen-bonded sheet structure through hy-droxy O - H⋯O hydrogen-bonded links. The anilinium groups of the 4-(phenyl-diazenyl)-anilinium cations are incorporated into the sheets and also provide inter-nal hydrogen-bonded extensions, while their aromatic tails are layered in the structure without significant association except for weak π-π inter-actions [minimum ring centroid separation = 3.844 (3) Å]. The hydrogen l-tartrate residues of both anions exhibit the common short intra-molecular hy-droxy-carboxylate O - H⋯O hydogen bonds. This work provides a solution to the unusual disorder problem inherent in the structure of this salt, as well as giving another example of the utility of the hydrogen tartrate anion in the generation of sheet substructures in mol-ecular assembly processes.

Original languageEnglish
Pages (from-to)o345-o348
Number of pages4
JournalActa Crystallographica Section C: Crystal Structure Communications
VolumeC66
Issue numberPart 7
DOIs
Publication statusPublished - 16 Jul 2010
Externally publishedYes

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p-Aminoazobenzene
Proton transfer
Aniline
aniline
Protons
Hydrogen
Coloring Agents
Dyes
Salts
dyes
disorders
salts
acids
protons
Acids
rings
hydrogen
Anions
Negative ions
anions

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@article{8b4c92fafb7f418bb41e1bccad6bfdf3,
title = "Phenyl-ring rotational disorder in the two-dimensional hydrogen-bonded structure of the 1:1 proton-transfer salt of the diazo-dye precursor 4-(phenyl-diazenyl)aniline (aniline yellow) with l-tartaric acid",
abstract = "In the structure of the 1:1 proton-transfer compound from the reaction of l-tartaric acid with the azo-dye precursor aniline yellow [4-(phenyl - diazenyl)aniline], namely 4-(phenyl-di-az-enyl)-anilinium (2R,3R)-3-carb-oxy-2, 3-dihy-droxy-propano-ate, C12H12N3 +·C4H5O6 -, the asymmetric unit contains two independent 4-(phenyl-diazenyl)-anilinium cations and two hydrogen l-tartrate anions. The structure is unusual in that all four phenyl rings of the two cations have identical rotational disorder with equal occupancy of the conformations. The two hydrogen l-tartrate anions form independent but similar chains through head-to-tail carboxyl-carboxyl-ate O - H⋯O hydrogen bonds [graph set C(7)], which are then extended into a two-dimensional hydrogen-bonded sheet structure through hy-droxy O - H⋯O hydrogen-bonded links. The anilinium groups of the 4-(phenyl-diazenyl)-anilinium cations are incorporated into the sheets and also provide inter-nal hydrogen-bonded extensions, while their aromatic tails are layered in the structure without significant association except for weak π-π inter-actions [minimum ring centroid separation = 3.844 (3) {\AA}]. The hydrogen l-tartrate residues of both anions exhibit the common short intra-molecular hy-droxy-carboxylate O - H⋯O hydogen bonds. This work provides a solution to the unusual disorder problem inherent in the structure of this salt, as well as giving another example of the utility of the hydrogen tartrate anion in the generation of sheet substructures in mol-ecular assembly processes.",
author = "Graham Smith and Wermuth, {Urs D.} and Young, {David J.}",
year = "2010",
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doi = "10.1107/S0108270110020597",
language = "English",
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journal = "Acta Crystallographica Section C: Structural Chemistry",
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TY - JOUR

T1 - Phenyl-ring rotational disorder in the two-dimensional hydrogen-bonded structure of the 1:1 proton-transfer salt of the diazo-dye precursor 4-(phenyl-diazenyl)aniline (aniline yellow) with l-tartaric acid

AU - Smith, Graham

AU - Wermuth, Urs D.

AU - Young, David J.

PY - 2010/7/16

Y1 - 2010/7/16

N2 - In the structure of the 1:1 proton-transfer compound from the reaction of l-tartaric acid with the azo-dye precursor aniline yellow [4-(phenyl - diazenyl)aniline], namely 4-(phenyl-di-az-enyl)-anilinium (2R,3R)-3-carb-oxy-2, 3-dihy-droxy-propano-ate, C12H12N3 +·C4H5O6 -, the asymmetric unit contains two independent 4-(phenyl-diazenyl)-anilinium cations and two hydrogen l-tartrate anions. The structure is unusual in that all four phenyl rings of the two cations have identical rotational disorder with equal occupancy of the conformations. The two hydrogen l-tartrate anions form independent but similar chains through head-to-tail carboxyl-carboxyl-ate O - H⋯O hydrogen bonds [graph set C(7)], which are then extended into a two-dimensional hydrogen-bonded sheet structure through hy-droxy O - H⋯O hydrogen-bonded links. The anilinium groups of the 4-(phenyl-diazenyl)-anilinium cations are incorporated into the sheets and also provide inter-nal hydrogen-bonded extensions, while their aromatic tails are layered in the structure without significant association except for weak π-π inter-actions [minimum ring centroid separation = 3.844 (3) Å]. The hydrogen l-tartrate residues of both anions exhibit the common short intra-molecular hy-droxy-carboxylate O - H⋯O hydogen bonds. This work provides a solution to the unusual disorder problem inherent in the structure of this salt, as well as giving another example of the utility of the hydrogen tartrate anion in the generation of sheet substructures in mol-ecular assembly processes.

AB - In the structure of the 1:1 proton-transfer compound from the reaction of l-tartaric acid with the azo-dye precursor aniline yellow [4-(phenyl - diazenyl)aniline], namely 4-(phenyl-di-az-enyl)-anilinium (2R,3R)-3-carb-oxy-2, 3-dihy-droxy-propano-ate, C12H12N3 +·C4H5O6 -, the asymmetric unit contains two independent 4-(phenyl-diazenyl)-anilinium cations and two hydrogen l-tartrate anions. The structure is unusual in that all four phenyl rings of the two cations have identical rotational disorder with equal occupancy of the conformations. The two hydrogen l-tartrate anions form independent but similar chains through head-to-tail carboxyl-carboxyl-ate O - H⋯O hydrogen bonds [graph set C(7)], which are then extended into a two-dimensional hydrogen-bonded sheet structure through hy-droxy O - H⋯O hydrogen-bonded links. The anilinium groups of the 4-(phenyl-diazenyl)-anilinium cations are incorporated into the sheets and also provide inter-nal hydrogen-bonded extensions, while their aromatic tails are layered in the structure without significant association except for weak π-π inter-actions [minimum ring centroid separation = 3.844 (3) Å]. The hydrogen l-tartrate residues of both anions exhibit the common short intra-molecular hy-droxy-carboxylate O - H⋯O hydogen bonds. This work provides a solution to the unusual disorder problem inherent in the structure of this salt, as well as giving another example of the utility of the hydrogen tartrate anion in the generation of sheet substructures in mol-ecular assembly processes.

UR - http://www.scopus.com/inward/record.url?scp=77954468535&partnerID=8YFLogxK

U2 - 10.1107/S0108270110020597

DO - 10.1107/S0108270110020597

M3 - Article

VL - C66

SP - o345-o348

JO - Acta Crystallographica Section C: Structural Chemistry

JF - Acta Crystallographica Section C: Structural Chemistry

SN - 1600-5759

IS - Part 7

ER -