Cargando…
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(...
Autores principales: | , , , , |
---|---|
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 |
_version_ | 1782237803204050944 |
---|---|
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)]. |
format | Online Article Text |
id | pubmed-3394012 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT pinheiroluizcs 43fluoroanilinothieno23bpyridine6carboxylicacid AT bernardinoalicemr 43fluoroanilinothieno23bpyridine6carboxylicacid AT wardellsolangemsv 43fluoroanilinothieno23bpyridine6carboxylicacid AT wardelljamesl 43fluoroanilinothieno23bpyridine6carboxylicacid AT tiekinkedwardrt 43fluoroanilinothieno23bpyridine6carboxylicacid |