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2-Hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate
The zwitterionic title compound, C(16)H(12)N(2)O(3), was obtained as a result of the condensation of 5-aminosalicylic acid and 1H-indole-3-carbaldehyde. The whole molecule is roughly planar: the 4-hydroxyanilinic group and the 1H-indole-3-carbaldehyde moieties are only slightly twisted, making a...
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3011759/ https://www.ncbi.nlm.nih.gov/pubmed/21589591 http://dx.doi.org/10.1107/S1600536810048579 |
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author | Tahir, M. Nawaz Shad, Hazoor Ahmad |
author_facet | Tahir, M. Nawaz Shad, Hazoor Ahmad |
author_sort | Tahir, M. Nawaz |
collection | PubMed |
description | The zwitterionic title compound, C(16)H(12)N(2)O(3), was obtained as a result of the condensation of 5-aminosalicylic acid and 1H-indole-3-carbaldehyde. The whole molecule is roughly planar: the 4-hydroxyanilinic group and the 1H-indole-3-carbaldehyde moieties are only slightly twisted, making a dihedral angle of 7.77 (11)°, whereas, the carboxylate group makes a dihedral angle of 3.34 (45)° with the parent 4-hydroxyanilinic group. S(6) ring motifs are formed due to intramolecular O—H⋯O hydrogen bonding. In the crystal, intermolecular N—H⋯O and C—H⋯O hydrogen bonds build up pseudo-rings with R (1) (2)(4), R (2) (1)(7) and R (2) (2)(14) ring motifs. These pseudo-dimers are further linked by N—H⋯O hydrogen bonds into a chain extending along [101]. C—H⋯π interactions also occur, along with offset π–π interactions between the anilinic phenyl and the heterocyclic five-membered rings with a centroid–centroid distance of 3.5716 (19) Å. |
format | Text |
id | pubmed-3011759 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-30117592010-12-30 2-Hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate Tahir, M. Nawaz Shad, Hazoor Ahmad Acta Crystallogr Sect E Struct Rep Online Organic Papers The zwitterionic title compound, C(16)H(12)N(2)O(3), was obtained as a result of the condensation of 5-aminosalicylic acid and 1H-indole-3-carbaldehyde. The whole molecule is roughly planar: the 4-hydroxyanilinic group and the 1H-indole-3-carbaldehyde moieties are only slightly twisted, making a dihedral angle of 7.77 (11)°, whereas, the carboxylate group makes a dihedral angle of 3.34 (45)° with the parent 4-hydroxyanilinic group. S(6) ring motifs are formed due to intramolecular O—H⋯O hydrogen bonding. In the crystal, intermolecular N—H⋯O and C—H⋯O hydrogen bonds build up pseudo-rings with R (1) (2)(4), R (2) (1)(7) and R (2) (2)(14) ring motifs. These pseudo-dimers are further linked by N—H⋯O hydrogen bonds into a chain extending along [101]. C—H⋯π interactions also occur, along with offset π–π interactions between the anilinic phenyl and the heterocyclic five-membered rings with a centroid–centroid distance of 3.5716 (19) Å. International Union of Crystallography 2010-11-27 /pmc/articles/PMC3011759/ /pubmed/21589591 http://dx.doi.org/10.1107/S1600536810048579 Text en © Tahir and Shad 2010 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 Tahir, M. Nawaz Shad, Hazoor Ahmad 2-Hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate |
title | 2-Hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate |
title_full | 2-Hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate |
title_fullStr | 2-Hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate |
title_full_unstemmed | 2-Hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate |
title_short | 2-Hydroxy-5-[(E)-(1H-indol-3-ylmethylidene)azaniumyl]benzoate |
title_sort | 2-hydroxy-5-[(e)-(1h-indol-3-ylmethylidene)azaniumyl]benzoate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3011759/ https://www.ncbi.nlm.nih.gov/pubmed/21589591 http://dx.doi.org/10.1107/S1600536810048579 |
work_keys_str_mv | AT tahirmnawaz 2hydroxy5e1hindol3ylmethylideneazaniumylbenzoate AT shadhazoorahmad 2hydroxy5e1hindol3ylmethylideneazaniumylbenzoate |