Crystal structures of 3-chloro-2-nitrobenzoic acid with quinoline derivatives: 3-chloro-2-nitrobenzoic acid-5-nitroquinoline (1/1), 3-chloro-2-nitrobenzoic acid-6-nitroquinoline (1/1) and 8-hydroxyquinolinium 3-chloro-2-nitrobenzoate

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Abstract

The structures of three compounds of 3-chloro-2-nitrobenzoic acid with 5-nitroquinoline, (I), 6-nitroquinoline, (II), and 8-hydroxyquinoline, (III), have been determined at 190K. In each of the two isomeric compounds, (I) and (II), C7H4ClNO4·C9H6N2O2, the acid and base molecules are held together by O - H⋯N and C - H⋯O hydrogen bonds. In compound (III), C9H8NO+·C7H3ClNO4 -, an acid-base interaction involving H-atom transfer occurs and the H atom is located at the N site of the base molecule. In the crystal of (I), the hydrogen-bonded acid-base units are linked by C - H⋯O hydrogen bonds, forming a tape structure along the b-axis direction. Adjacent tapes, which are related by a twofold rotation axis, are linked by a third C - H⋯O hydrogen bond, forming wide ribbons parallel to the ( 03) plane. These ribbons are stacked via π-π interactions between the quinoline ring systems [centroid-centroid distances = 3.4935(5)-3.7721(6)Å], forming layers parallel to the ab plane. In the crystal of (II), the hydrogen-bonded acid-base units are also linked into a tape structure along the b-axis direction via C - H⋯O hydrogen bonds. Inversion-related tapes are linked by further C - H⋯O hydrogen bonds to form wide ribbons parallel to the ( 08) plane. The ribbons are linked by weak π-π interactions [centroid-centroid distances = 3.8016(8)-3.9247(9)Å], forming a three-dimensional structure. In the crystal of (III), the cations and the anions are alternately linked via N - H⋯O and O - H⋯O hydrogen bonds, forming a 21 helix running along the b-axis direction. The cations and the anions are further stacked alternately in columns along the a-axis direction via π-π interactions [centroid-centroid distances = 3.8016(8)-3.9247(9)Å], and the molecular chains are linked into layers parallel to the ab plane through these interactions.

Original languageEnglish
Pages (from-to)1552-1557
Number of pages6
JournalActa Crystallographica Section E: Crystallographic Communications
Volume75
DOIs
Publication statusPublished - Oct 1 2019

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Nitroquinolines
Nitrobenzoates
quinoline
centroids
Hydrogen bonds
Crystal structure
hydrogen bonds
Derivatives
Tapes
ribbons
tapes
acids
crystal structure
Acids
Crystals
Anions
Cations
Hydrogen
Negative ions
Positive ions

Keywords

  • 3-chloro-2-nitrobonzoic acid
  • 5-nitroquinoline
  • 6-nitroquinoline
  • 8-hydroxyqunoline
  • Crystal structure
  • Hydrogen bond

ASJC Scopus subject areas

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

Cite this

@article{c1666da0289f408fa594bff3691bd5e2,
title = "Crystal structures of 3-chloro-2-nitrobenzoic acid with quinoline derivatives: 3-chloro-2-nitrobenzoic acid-5-nitroquinoline (1/1), 3-chloro-2-nitrobenzoic acid-6-nitroquinoline (1/1) and 8-hydroxyquinolinium 3-chloro-2-nitrobenzoate",
abstract = "The structures of three compounds of 3-chloro-2-nitrobenzoic acid with 5-nitroquinoline, (I), 6-nitroquinoline, (II), and 8-hydroxyquinoline, (III), have been determined at 190K. In each of the two isomeric compounds, (I) and (II), C7H4ClNO4·C9H6N2O2, the acid and base molecules are held together by O - H⋯N and C - H⋯O hydrogen bonds. In compound (III), C9H8NO+·C7H3ClNO4 -, an acid-base interaction involving H-atom transfer occurs and the H atom is located at the N site of the base molecule. In the crystal of (I), the hydrogen-bonded acid-base units are linked by C - H⋯O hydrogen bonds, forming a tape structure along the b-axis direction. Adjacent tapes, which are related by a twofold rotation axis, are linked by a third C - H⋯O hydrogen bond, forming wide ribbons parallel to the ( 03) plane. These ribbons are stacked via π-π interactions between the quinoline ring systems [centroid-centroid distances = 3.4935(5)-3.7721(6){\AA}], forming layers parallel to the ab plane. In the crystal of (II), the hydrogen-bonded acid-base units are also linked into a tape structure along the b-axis direction via C - H⋯O hydrogen bonds. Inversion-related tapes are linked by further C - H⋯O hydrogen bonds to form wide ribbons parallel to the ( 08) plane. The ribbons are linked by weak π-π interactions [centroid-centroid distances = 3.8016(8)-3.9247(9){\AA}], forming a three-dimensional structure. In the crystal of (III), the cations and the anions are alternately linked via N - H⋯O and O - H⋯O hydrogen bonds, forming a 21 helix running along the b-axis direction. The cations and the anions are further stacked alternately in columns along the a-axis direction via π-π interactions [centroid-centroid distances = 3.8016(8)-3.9247(9){\AA}], and the molecular chains are linked into layers parallel to the ab plane through these interactions.",
keywords = "3-chloro-2-nitrobonzoic acid, 5-nitroquinoline, 6-nitroquinoline, 8-hydroxyqunoline, Crystal structure, Hydrogen bond",
author = "Kazuma Gotoh and Hiroyuki Ishida",
year = "2019",
month = "10",
day = "1",
doi = "10.1107/S2056989019012799",
language = "English",
volume = "75",
pages = "1552--1557",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Crystal structures of 3-chloro-2-nitrobenzoic acid with quinoline derivatives

T2 - 3-chloro-2-nitrobenzoic acid-5-nitroquinoline (1/1), 3-chloro-2-nitrobenzoic acid-6-nitroquinoline (1/1) and 8-hydroxyquinolinium 3-chloro-2-nitrobenzoate

AU - Gotoh, Kazuma

AU - Ishida, Hiroyuki

PY - 2019/10/1

Y1 - 2019/10/1

N2 - The structures of three compounds of 3-chloro-2-nitrobenzoic acid with 5-nitroquinoline, (I), 6-nitroquinoline, (II), and 8-hydroxyquinoline, (III), have been determined at 190K. In each of the two isomeric compounds, (I) and (II), C7H4ClNO4·C9H6N2O2, the acid and base molecules are held together by O - H⋯N and C - H⋯O hydrogen bonds. In compound (III), C9H8NO+·C7H3ClNO4 -, an acid-base interaction involving H-atom transfer occurs and the H atom is located at the N site of the base molecule. In the crystal of (I), the hydrogen-bonded acid-base units are linked by C - H⋯O hydrogen bonds, forming a tape structure along the b-axis direction. Adjacent tapes, which are related by a twofold rotation axis, are linked by a third C - H⋯O hydrogen bond, forming wide ribbons parallel to the ( 03) plane. These ribbons are stacked via π-π interactions between the quinoline ring systems [centroid-centroid distances = 3.4935(5)-3.7721(6)Å], forming layers parallel to the ab plane. In the crystal of (II), the hydrogen-bonded acid-base units are also linked into a tape structure along the b-axis direction via C - H⋯O hydrogen bonds. Inversion-related tapes are linked by further C - H⋯O hydrogen bonds to form wide ribbons parallel to the ( 08) plane. The ribbons are linked by weak π-π interactions [centroid-centroid distances = 3.8016(8)-3.9247(9)Å], forming a three-dimensional structure. In the crystal of (III), the cations and the anions are alternately linked via N - H⋯O and O - H⋯O hydrogen bonds, forming a 21 helix running along the b-axis direction. The cations and the anions are further stacked alternately in columns along the a-axis direction via π-π interactions [centroid-centroid distances = 3.8016(8)-3.9247(9)Å], and the molecular chains are linked into layers parallel to the ab plane through these interactions.

AB - The structures of three compounds of 3-chloro-2-nitrobenzoic acid with 5-nitroquinoline, (I), 6-nitroquinoline, (II), and 8-hydroxyquinoline, (III), have been determined at 190K. In each of the two isomeric compounds, (I) and (II), C7H4ClNO4·C9H6N2O2, the acid and base molecules are held together by O - H⋯N and C - H⋯O hydrogen bonds. In compound (III), C9H8NO+·C7H3ClNO4 -, an acid-base interaction involving H-atom transfer occurs and the H atom is located at the N site of the base molecule. In the crystal of (I), the hydrogen-bonded acid-base units are linked by C - H⋯O hydrogen bonds, forming a tape structure along the b-axis direction. Adjacent tapes, which are related by a twofold rotation axis, are linked by a third C - H⋯O hydrogen bond, forming wide ribbons parallel to the ( 03) plane. These ribbons are stacked via π-π interactions between the quinoline ring systems [centroid-centroid distances = 3.4935(5)-3.7721(6)Å], forming layers parallel to the ab plane. In the crystal of (II), the hydrogen-bonded acid-base units are also linked into a tape structure along the b-axis direction via C - H⋯O hydrogen bonds. Inversion-related tapes are linked by further C - H⋯O hydrogen bonds to form wide ribbons parallel to the ( 08) plane. The ribbons are linked by weak π-π interactions [centroid-centroid distances = 3.8016(8)-3.9247(9)Å], forming a three-dimensional structure. In the crystal of (III), the cations and the anions are alternately linked via N - H⋯O and O - H⋯O hydrogen bonds, forming a 21 helix running along the b-axis direction. The cations and the anions are further stacked alternately in columns along the a-axis direction via π-π interactions [centroid-centroid distances = 3.8016(8)-3.9247(9)Å], and the molecular chains are linked into layers parallel to the ab plane through these interactions.

KW - 3-chloro-2-nitrobonzoic acid

KW - 5-nitroquinoline

KW - 6-nitroquinoline

KW - 8-hydroxyqunoline

KW - Crystal structure

KW - Hydrogen bond

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U2 - 10.1107/S2056989019012799

DO - 10.1107/S2056989019012799

M3 - Article

AN - SCOPUS:85073076998

VL - 75

SP - 1552

EP - 1557

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

ER -