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ID 57581
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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 three compounds of 3-chloro-2-nitrobenzoic acid with 5-nitroquinoline, (I), 6-nitroquinoline, (II), and 8-hydroxyquinoline, (III), have been determined at 190 K. In each of the two isomeric compounds, (I) and (II), C7H4ClNO4 center dot C9H6N2O2, the acid and base molecules are held together by O - H center dot center dot center dot N and C - H center dot center dot center dot O hydrogen bonds. In compound (III), C9H8NO+center dot-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 center dot center dot center dot 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 center dot center dot center dot O hydrogen bond, forming wide ribbons parallel to the ((1) over bar 03) plane. These ribbons are stacked via pi-pi interactions between the quinoline ring systems [centroid-centroid distances = 3.4935 (5)-3.7721 (6) angstrom], 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 center dot center dot center dot O hydrogen bonds. Inversion-related tapes are linked by further C-H center dot center dot center dot O hydrogen bonds to form wide ribbons parallel to the ((3) over bar 08) plane. The ribbons are linked by weak pi-pi interactions [centroid-centroid distances = 3.8016 (8)-3.9247 (9) angstrom], forming a three-dimensional structure. In the crystal of (III), the cations and the anions are alternately linked via N - H center dot center dot center dot O and O - H center dot center dot center dot-O hydrogen bonds, forming a 2(1) helix running along the b-axis direction. The cations and the anions are further stacked alternately in columns along the a-axis direction via pi-pi interactions [centroid-centroid distances = 3.8016 (8)-3.9247 (9) angstrom], and the molecular chains are linked into layers parallel to the ab plane through these interactions.
Keywords
crystal structure
3-chloro-2-nitrobonzoic acid
5-nitroquinoline
6-nitroquinoline
8-hydroxyqunoline
hydrogen bond
Published Date
2019-10
Publication Title
Acta Crystallographica Section E: Crystallographic Communications
Volume
volume75
Issue
issue10
Publisher
INT UNION CRYSTALLOGRAPHY
Start Page
1552
End Page
1557
ISSN
2056-9890
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
Copyright Holders
2019 authors
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publisher
PubMed ID
DOI
Web of Science KeyUT
Related Url
isVersionOf https://doi.org/10.1107/S2056989019012799
License
https://creativecommons.org/licenses/by/4.0/