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Gotoh, Kazuma Department of Chemistry, Faculty of Science, Okayama University Kaken ID researchmap
Ishida, Hiroyuki Department of Chemistry, Faculty of Science, Okayama University Kaken ID publons researchmap
Abstract
The structures of the four isomeric compounds of 6-methyl­quinoline with chloro- and nitro-substituted benzoic acids, C7H4ClNO4·C10H9N, namely, 2-chloro-4-nitro­benzoic acid–6-methyl­quinoline (1/1), (I), 2-chloro-5-nitro­benzoic acid–6-methyl­quinoline (1/1), (II), 3-chloro-2-nitro­benzoic acid–6-methyl­quinoline (1/1), (III), and 4-chloro-2-nitro­benzoic acid–6-methyl­quinoline (1/1), (IV), have been determined at 185–190 K. In each compound, the acid and base mol­ecules are linked by a short hydrogen bond between a carboxyl O atom and an N atom of the base. The O⋯N distances are 2.5452 (12), 2.6569 (13), 2.5640 (17) and 2.514 (2) Å, respectively, for compounds (I)–(IV). In the hydrogen-bonded acid–base units of (I), (III) and (IV), the H atoms are each disordered over two positions with O site:N site occupancies of 0.65 (3):0.35 (3), 0.59 (4):0.41 (4) and 0.48 (5):0.52 (5), respectively, for (I), (III) and (IV). The H atom in the hydrogen-bonded unit of (II) is located at the O-atom site. In all of the crystals of (I)–(IV), π–π inter­actions between the quinoline ring system and the benzene ring of the acid mol­ecule are observed. In addition, a π–π inter­action between the benzene rings of adjacent acid mol­ecules and a C—H⋯O hydrogen bond are observed in the crystal of (I), and C—H⋯O hydrogen bonds and O⋯Cl contacts occur in the crystals of (III) and (IV). These inter­molecular inter­actions connect the acid and base mol­ecules, forming a layer structure parallel to the bc plane in (I), a column along the a-axis direction in (II), a layer parallel to the ab plane in (III) and a three-dimensional network in (IV). Hirshfeld surfaces for the title compounds mapped over dnorm and shape index were generated to visualize the weak inter­molecular inter­actions.
Keywords
crystal structure
2-chloro-4-nitro­benzoic acid
2-chloro-5-nitro­benzoic acid
3-chloro-2-nitro­benzoic acid
4-chloro-2-nitro­benzoic acid
6-methyl­quinoline
hydrogen bond
disorder
Hirshfeld surface
Published Date
2020-11
Publication Title
Acta Crystallographica Section E: Crystallographic Communications
Volume
volume76
Issue
issue11
Publisher
International Union of Crystallography
Start Page
1701
End Page
1707
ISSN
2056-9890
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
Copyright Holders
© Authors.
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DOI
Web of Science KeyUT
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isVersionOf https://doi.org/10.1107/S2056989020013134
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https://creativecommons.org/licenses/by/4.0/