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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...
Autores principales: | , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
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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 |
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. |
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