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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...

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Autores principales: Suchetan, P. A., Prakash, Shet M., Lokanath, N. K., Naveen, S., Warad, Ismail
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
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%).
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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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