Crystal structure of 4-chloro-2-nitrobenzoic acid with 4-hydroxyquinoline: a disordered structure over two states of 4-chloro-2-nitrobenzoic acid-quinolin-4(1H)-one (1/1) and 4-hydroxyquinolinium 4-chloro-2-nitrobenzoate

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Abstract

The title compound, C9H7.5NO·C7H3.5ClNO4, was analysed as a disordered structure over two states, viz. co-crystal and salt, accompanied by a keto-enol tautomerization in the base molecule. The co-crystal is 4-chloro-2-nitrobenzoic acid-quinolin-4(1H)-one (1/1), C7H4ClNO4·C9H7NO, and the salt is 4-hydroxyquinolinium 4-chloro-2-nitrobenzoate, C9H8NO+·C7H3ClNO4 -. In the compound, the acid and base molecules are held together by a short hydrogen bond [O⋯O = 2.4393(15)Å], in which the H atom is disordered over two positions with equal occupancies. In the crystal, the hydrogen-bonded acid-base units are linked by N - H⋯O and C - H⋯O hydrogen bonds, forming a tape structure along the a-axis direction. The tapes are stacked into a layer parallel to the ab plane via π-π interactions [centroid-centroid distances = 3.5504(8)-3.9010(11)Å]. The layers are further linked by another C - H⋯O hydrogen bond, forming a three-dimensional network. Hirshfeld surfaces for the title compound mapped over shape-index and d norm were generated to visualize the intermolecular interactions.

Original languageEnglish
Pages (from-to)1853-1856
Number of pages4
JournalActa Crystallographica Section E: Crystallographic Communications
Volume75
DOIs
Publication statusPublished - Dec 1 2019

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quinoline
Hydrogen bonds
Crystal structure
hydrogen bonds
centroids
Tapes
Crystals
tapes
acids
crystal structure
Acids
Salts
salts
crystals
Molecules
norms
molecules
Hydrogen
interactions
Atoms

Keywords

  • 4(1H)-quinolinone
  • 4-chloro-2-nitrobenzoic acid
  • 4-hydroxyquinoline
  • crystal structure
  • Hirshfeld surface
  • hydrogen bond
  • keto-enol tautomerization

ASJC Scopus subject areas

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

Cite this

@article{1fa5c9981649454bbb6eff6026f9c83c,
title = "Crystal structure of 4-chloro-2-nitrobenzoic acid with 4-hydroxyquinoline: a disordered structure over two states of 4-chloro-2-nitrobenzoic acid-quinolin-4(1H)-one (1/1) and 4-hydroxyquinolinium 4-chloro-2-nitrobenzoate",
abstract = "The title compound, C9H7.5NO·C7H3.5ClNO4, was analysed as a disordered structure over two states, viz. co-crystal and salt, accompanied by a keto-enol tautomerization in the base molecule. The co-crystal is 4-chloro-2-nitrobenzoic acid-quinolin-4(1H)-one (1/1), C7H4ClNO4·C9H7NO, and the salt is 4-hydroxyquinolinium 4-chloro-2-nitrobenzoate, C9H8NO+·C7H3ClNO4 -. In the compound, the acid and base molecules are held together by a short hydrogen bond [O⋯O = 2.4393(15){\AA}], in which the H atom is disordered over two positions with equal occupancies. In the crystal, the hydrogen-bonded acid-base units are linked by N - H⋯O and C - H⋯O hydrogen bonds, forming a tape structure along the a-axis direction. The tapes are stacked into a layer parallel to the ab plane via π-π interactions [centroid-centroid distances = 3.5504(8)-3.9010(11){\AA}]. The layers are further linked by another C - H⋯O hydrogen bond, forming a three-dimensional network. Hirshfeld surfaces for the title compound mapped over shape-index and d norm were generated to visualize the intermolecular interactions.",
keywords = "4(1H)-quinolinone, 4-chloro-2-nitrobenzoic acid, 4-hydroxyquinoline, crystal structure, Hirshfeld surface, hydrogen bond, keto-enol tautomerization",
author = "Kazuma Gotoh and Hiroyuki Ishida",
year = "2019",
month = "12",
day = "1",
doi = "10.1107/S205698901901497X",
language = "English",
volume = "75",
pages = "1853--1856",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Crystal structure of 4-chloro-2-nitrobenzoic acid with 4-hydroxyquinoline

T2 - a disordered structure over two states of 4-chloro-2-nitrobenzoic acid-quinolin-4(1H)-one (1/1) and 4-hydroxyquinolinium 4-chloro-2-nitrobenzoate

AU - Gotoh, Kazuma

AU - Ishida, Hiroyuki

PY - 2019/12/1

Y1 - 2019/12/1

N2 - The title compound, C9H7.5NO·C7H3.5ClNO4, was analysed as a disordered structure over two states, viz. co-crystal and salt, accompanied by a keto-enol tautomerization in the base molecule. The co-crystal is 4-chloro-2-nitrobenzoic acid-quinolin-4(1H)-one (1/1), C7H4ClNO4·C9H7NO, and the salt is 4-hydroxyquinolinium 4-chloro-2-nitrobenzoate, C9H8NO+·C7H3ClNO4 -. In the compound, the acid and base molecules are held together by a short hydrogen bond [O⋯O = 2.4393(15)Å], in which the H atom is disordered over two positions with equal occupancies. In the crystal, the hydrogen-bonded acid-base units are linked by N - H⋯O and C - H⋯O hydrogen bonds, forming a tape structure along the a-axis direction. The tapes are stacked into a layer parallel to the ab plane via π-π interactions [centroid-centroid distances = 3.5504(8)-3.9010(11)Å]. The layers are further linked by another C - H⋯O hydrogen bond, forming a three-dimensional network. Hirshfeld surfaces for the title compound mapped over shape-index and d norm were generated to visualize the intermolecular interactions.

AB - The title compound, C9H7.5NO·C7H3.5ClNO4, was analysed as a disordered structure over two states, viz. co-crystal and salt, accompanied by a keto-enol tautomerization in the base molecule. The co-crystal is 4-chloro-2-nitrobenzoic acid-quinolin-4(1H)-one (1/1), C7H4ClNO4·C9H7NO, and the salt is 4-hydroxyquinolinium 4-chloro-2-nitrobenzoate, C9H8NO+·C7H3ClNO4 -. In the compound, the acid and base molecules are held together by a short hydrogen bond [O⋯O = 2.4393(15)Å], in which the H atom is disordered over two positions with equal occupancies. In the crystal, the hydrogen-bonded acid-base units are linked by N - H⋯O and C - H⋯O hydrogen bonds, forming a tape structure along the a-axis direction. The tapes are stacked into a layer parallel to the ab plane via π-π interactions [centroid-centroid distances = 3.5504(8)-3.9010(11)Å]. The layers are further linked by another C - H⋯O hydrogen bond, forming a three-dimensional network. Hirshfeld surfaces for the title compound mapped over shape-index and d norm were generated to visualize the intermolecular interactions.

KW - 4(1H)-quinolinone

KW - 4-chloro-2-nitrobenzoic acid

KW - 4-hydroxyquinoline

KW - crystal structure

KW - Hirshfeld surface

KW - hydrogen bond

KW - keto-enol tautomerization

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U2 - 10.1107/S205698901901497X

DO - 10.1107/S205698901901497X

M3 - Article

AN - SCOPUS:85076374196

VL - 75

SP - 1853

EP - 1856

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

ER -