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N-[2-(Trifluoromethyl)phenyl]maleamic acid: crystal structure and Hirshfeld surface analysis
The title molecule, C(11)H(8)F(3)NO(3), adopts a cis configuration across the –C=C– double bond in the side chain and the dihedral angle between the phenyl ring and side chain is 47.35 (1)°. The –COOH group adopts a syn conformation (O=C—O—H = 0°), unlike the anti conformation observed in related m...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658960/ https://www.ncbi.nlm.nih.gov/pubmed/31391962 http://dx.doi.org/10.1107/S2056989019006509 |
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author | Suchetan, P. A. Prakash, Shet M. Lokanath, N. K. Naveen, S. Warad, Ismail |
author_facet | Suchetan, P. A. Prakash, Shet M. Lokanath, N. K. Naveen, S. Warad, Ismail |
author_sort | Suchetan, P. A. |
collection | PubMed |
description | The title molecule, C(11)H(8)F(3)NO(3), adopts a cis configuration across the –C=C– double bond in the side chain and the dihedral angle between the phenyl ring and side chain is 47.35 (1)°. The –COOH group adopts a syn conformation (O=C—O—H = 0°), unlike the anti conformation observed in related maleamic acids. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds are connected via N—H⋯O hydrogen bonds and C—H⋯O interactions into (100) sheets, which are cross-linked by another C—H⋯O interaction to result in a three-dimensional network. The Hirshfeld surface fingerprint plots show that the highest contribution to surface contacts arises from O⋯H/H⋯O contacts (26.5%) followed by H⋯F/F⋯H (23.4%) and H⋯H (17.3%). |
format | Online Article Text |
id | pubmed-6658960 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-66589602019-08-07 N-[2-(Trifluoromethyl)phenyl]maleamic acid: crystal structure and Hirshfeld surface analysis Suchetan, P. A. Prakash, Shet M. Lokanath, N. K. Naveen, S. Warad, Ismail Acta Crystallogr E Crystallogr Commun Research Communications The title molecule, C(11)H(8)F(3)NO(3), adopts a cis configuration across the –C=C– double bond in the side chain and the dihedral angle between the phenyl ring and side chain is 47.35 (1)°. The –COOH group adopts a syn conformation (O=C—O—H = 0°), unlike the anti conformation observed in related maleamic acids. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds are connected via N—H⋯O hydrogen bonds and C—H⋯O interactions into (100) sheets, which are cross-linked by another C—H⋯O interaction to result in a three-dimensional network. The Hirshfeld surface fingerprint plots show that the highest contribution to surface contacts arises from O⋯H/H⋯O contacts (26.5%) followed by H⋯F/F⋯H (23.4%) and H⋯H (17.3%). International Union of Crystallography 2019-05-10 /pmc/articles/PMC6658960/ /pubmed/31391962 http://dx.doi.org/10.1107/S2056989019006509 Text en © Suchetan et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Suchetan, P. A. Prakash, Shet M. Lokanath, N. K. Naveen, S. Warad, Ismail N-[2-(Trifluoromethyl)phenyl]maleamic acid: crystal structure and Hirshfeld surface analysis |
title |
N-[2-(Trifluoromethyl)phenyl]maleamic acid: crystal structure and Hirshfeld surface analysis |
title_full |
N-[2-(Trifluoromethyl)phenyl]maleamic acid: crystal structure and Hirshfeld surface analysis |
title_fullStr |
N-[2-(Trifluoromethyl)phenyl]maleamic acid: crystal structure and Hirshfeld surface analysis |
title_full_unstemmed |
N-[2-(Trifluoromethyl)phenyl]maleamic acid: crystal structure and Hirshfeld surface analysis |
title_short |
N-[2-(Trifluoromethyl)phenyl]maleamic acid: crystal structure and Hirshfeld surface analysis |
title_sort | n-[2-(trifluoromethyl)phenyl]maleamic acid: crystal structure and hirshfeld surface analysis |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658960/ https://www.ncbi.nlm.nih.gov/pubmed/31391962 http://dx.doi.org/10.1107/S2056989019006509 |
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