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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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Detalles Bibliográficos
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
Descripción
Sumario: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.