Crystal structures of isoquinoline-3-chloro-2-nitro-benzoic acid (1/1) and isoquinolinium 4-chloro-2-nitrobenzoate

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Abstract

In each of the title isomeric compounds, C9H7.3N·C7H3.7ClNO4, (I), and C9H8N·C7H3ClNO4, (II), of isoquinoline with 3-chloro-2-nitrobenzoic acid and 4-chloro-2-nitrobenzoic acid, the two components are linked by a short hydrogen bond between a base N atom and a carboxy O atom. In the hydrogen-bonded unit of (I), the H atom is disordered over two positions with N and O site occupancies of 0.30 (3) and 0.70 (3), respectively, while in (II), an acid-base interaction involving H-atom transfer occurs and the H atom is located at the N site. In the crystal of (I), the acid-base units are connected through C - H⋯O hydrogen bonds into a tape structure along the b-axis direction. Inversion-related adjacent tapes are further linked through π-π interactions [centroid-centroid distances = 3.6389 (7)-3.7501 (7) Á], forming a layer parallel to (001). In the crystal of (II), the acid-base units are connected through C - H⋯O hydrogen bonds into a ladder structure along the a-axis direction. The ladders are further linked by another C - H⋯O hydrogen bond into a layer parallel to (001).

Original languageEnglish
Pages (from-to)31-34
Number of pages4
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number1
DOIs
Publication statusPublished - Jan 1 2015

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Benzoic Acid
Benzoic acid
benzoic acid
Crystal structure
Hydrogen bonds
Atoms
acids
crystal structure
Acids
hydrogen bonds
atoms
Ladders
ladders
centroids
Tapes
tapes
Hydrogen
Crystals
crystals
isoquinoline

Keywords

  • Chloro- and nitro-substituted benzoic acid
  • Crystal structure
  • Isoquinoline
  • Short hydrogen bond

ASJC Scopus subject areas

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

Cite this

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title = "Crystal structures of isoquinoline-3-chloro-2-nitro-benzoic acid (1/1) and isoquinolinium 4-chloro-2-nitrobenzoate",
abstract = "In each of the title isomeric compounds, C9H7.3N·C7H3.7ClNO4, (I), and C9H8N·C7H3ClNO4, (II), of isoquinoline with 3-chloro-2-nitrobenzoic acid and 4-chloro-2-nitrobenzoic acid, the two components are linked by a short hydrogen bond between a base N atom and a carboxy O atom. In the hydrogen-bonded unit of (I), the H atom is disordered over two positions with N and O site occupancies of 0.30 (3) and 0.70 (3), respectively, while in (II), an acid-base interaction involving H-atom transfer occurs and the H atom is located at the N site. In the crystal of (I), the acid-base units are connected through C - H⋯O hydrogen bonds into a tape structure along the b-axis direction. Inversion-related adjacent tapes are further linked through π-π interactions [centroid-centroid distances = 3.6389 (7)-3.7501 (7) {\'A}], forming a layer parallel to (001). In the crystal of (II), the acid-base units are connected through C - H⋯O hydrogen bonds into a ladder structure along the a-axis direction. The ladders are further linked by another C - H⋯O hydrogen bond into a layer parallel to (001).",
keywords = "Chloro- and nitro-substituted benzoic acid, Crystal structure, Isoquinoline, Short hydrogen bond",
author = "Kazuma Gotoh and Hiroyuki Ishida and Lough, {A. J.}",
year = "2015",
month = "1",
day = "1",
doi = "10.1107/S2056989014026152",
language = "English",
volume = "71",
pages = "31--34",
journal = "Acta Crystallographica Section E: Structure Reports Online",
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TY - JOUR

T1 - Crystal structures of isoquinoline-3-chloro-2-nitro-benzoic acid (1/1) and isoquinolinium 4-chloro-2-nitrobenzoate

AU - Gotoh, Kazuma

AU - Ishida, Hiroyuki

AU - Lough, A. J.

PY - 2015/1/1

Y1 - 2015/1/1

N2 - In each of the title isomeric compounds, C9H7.3N·C7H3.7ClNO4, (I), and C9H8N·C7H3ClNO4, (II), of isoquinoline with 3-chloro-2-nitrobenzoic acid and 4-chloro-2-nitrobenzoic acid, the two components are linked by a short hydrogen bond between a base N atom and a carboxy O atom. In the hydrogen-bonded unit of (I), the H atom is disordered over two positions with N and O site occupancies of 0.30 (3) and 0.70 (3), respectively, while in (II), an acid-base interaction involving H-atom transfer occurs and the H atom is located at the N site. In the crystal of (I), the acid-base units are connected through C - H⋯O hydrogen bonds into a tape structure along the b-axis direction. Inversion-related adjacent tapes are further linked through π-π interactions [centroid-centroid distances = 3.6389 (7)-3.7501 (7) Á], forming a layer parallel to (001). In the crystal of (II), the acid-base units are connected through C - H⋯O hydrogen bonds into a ladder structure along the a-axis direction. The ladders are further linked by another C - H⋯O hydrogen bond into a layer parallel to (001).

AB - In each of the title isomeric compounds, C9H7.3N·C7H3.7ClNO4, (I), and C9H8N·C7H3ClNO4, (II), of isoquinoline with 3-chloro-2-nitrobenzoic acid and 4-chloro-2-nitrobenzoic acid, the two components are linked by a short hydrogen bond between a base N atom and a carboxy O atom. In the hydrogen-bonded unit of (I), the H atom is disordered over two positions with N and O site occupancies of 0.30 (3) and 0.70 (3), respectively, while in (II), an acid-base interaction involving H-atom transfer occurs and the H atom is located at the N site. In the crystal of (I), the acid-base units are connected through C - H⋯O hydrogen bonds into a tape structure along the b-axis direction. Inversion-related adjacent tapes are further linked through π-π interactions [centroid-centroid distances = 3.6389 (7)-3.7501 (7) Á], forming a layer parallel to (001). In the crystal of (II), the acid-base units are connected through C - H⋯O hydrogen bonds into a ladder structure along the a-axis direction. The ladders are further linked by another C - H⋯O hydrogen bond into a layer parallel to (001).

KW - Chloro- and nitro-substituted benzoic acid

KW - Crystal structure

KW - Isoquinoline

KW - Short hydrogen bond

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