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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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Autores principales: Tahir, M. Nawaz, Shad, Hazoor Ahmad
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
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.
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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
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