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4-(3-Fluoro­anilino)thieno[2,3-b]pyridine-6-carb­oxy­lic acid

In the title compound, C(14)H(9)FN(2)O(2)S, the thieno[2,3-b]pyridine residue is almost planar (r.m.s. deviation = 0.0194 Å), with the carb­oxy­lic acid group [dihedral angle = 11.9 (3)°] and the benzene ring [71.1 (4)°] being twisted out of this plane to different extents. An intra­molecular N—H⋯O(...

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Detalles Bibliográficos
Autores principales: Pinheiro, Luiz C. S., Bernardino, Alice M. R., Wardell, Solange M. S. V., Wardell, James L., Tiekink, Edward R. T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3394012/
https://www.ncbi.nlm.nih.gov/pubmed/22798877
http://dx.doi.org/10.1107/S1600536812027195
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author Pinheiro, Luiz C. S.
Bernardino, Alice M. R.
Wardell, Solange M. S. V.
Wardell, James L.
Tiekink, Edward R. T.
author_facet Pinheiro, Luiz C. S.
Bernardino, Alice M. R.
Wardell, Solange M. S. V.
Wardell, James L.
Tiekink, Edward R. T.
author_sort Pinheiro, Luiz C. S.
collection PubMed
description In the title compound, C(14)H(9)FN(2)O(2)S, the thieno[2,3-b]pyridine residue is almost planar (r.m.s. deviation = 0.0194 Å), with the carb­oxy­lic acid group [dihedral angle = 11.9 (3)°] and the benzene ring [71.1 (4)°] being twisted out of this plane to different extents. An intra­molecular N—H⋯O(carbon­yl) hydrogen bond closes an S(6) ring. Supra­molecular chains along [01-1] mediated by O—H⋯N(pyridine) hydrogen bonds feature in the crystal. A three-dimensional architecture is completed by π–π inter­actions occurring between the benzene ring and the two rings of the thieno[2,3-b]pyridine residue [centroid–centroid distances = 3.6963 (13) and 3.3812 (13) Å]. The F atom is disordered over the two meta sites in a near statistical ratio [0.545 (5):0.455 (5)].
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spelling pubmed-33940122012-07-13 4-(3-Fluoro­anilino)thieno[2,3-b]pyridine-6-carb­oxy­lic acid Pinheiro, Luiz C. S. Bernardino, Alice M. R. Wardell, Solange M. S. V. Wardell, James L. Tiekink, Edward R. T. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(14)H(9)FN(2)O(2)S, the thieno[2,3-b]pyridine residue is almost planar (r.m.s. deviation = 0.0194 Å), with the carb­oxy­lic acid group [dihedral angle = 11.9 (3)°] and the benzene ring [71.1 (4)°] being twisted out of this plane to different extents. An intra­molecular N—H⋯O(carbon­yl) hydrogen bond closes an S(6) ring. Supra­molecular chains along [01-1] mediated by O—H⋯N(pyridine) hydrogen bonds feature in the crystal. A three-dimensional architecture is completed by π–π inter­actions occurring between the benzene ring and the two rings of the thieno[2,3-b]pyridine residue [centroid–centroid distances = 3.6963 (13) and 3.3812 (13) Å]. The F atom is disordered over the two meta sites in a near statistical ratio [0.545 (5):0.455 (5)]. International Union of Crystallography 2012-06-27 /pmc/articles/PMC3394012/ /pubmed/22798877 http://dx.doi.org/10.1107/S1600536812027195 Text en © Pinheiro et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Pinheiro, Luiz C. S.
Bernardino, Alice M. R.
Wardell, Solange M. S. V.
Wardell, James L.
Tiekink, Edward R. T.
4-(3-Fluoro­anilino)thieno[2,3-b]pyridine-6-carb­oxy­lic acid
title 4-(3-Fluoro­anilino)thieno[2,3-b]pyridine-6-carb­oxy­lic acid
title_full 4-(3-Fluoro­anilino)thieno[2,3-b]pyridine-6-carb­oxy­lic acid
title_fullStr 4-(3-Fluoro­anilino)thieno[2,3-b]pyridine-6-carb­oxy­lic acid
title_full_unstemmed 4-(3-Fluoro­anilino)thieno[2,3-b]pyridine-6-carb­oxy­lic acid
title_short 4-(3-Fluoro­anilino)thieno[2,3-b]pyridine-6-carb­oxy­lic acid
title_sort 4-(3-fluoro­anilino)thieno[2,3-b]pyridine-6-carb­oxy­lic acid
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3394012/
https://www.ncbi.nlm.nih.gov/pubmed/22798877
http://dx.doi.org/10.1107/S1600536812027195
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