In the title compound, C22H14ClN3O2, the indole unit is essentially coplanar, with a maximum deviation of 0.035 Å for the C atom bearing the methyl group. The central pyridine ring is inclined to the indole ring system by 43.7 (1)°. The dihedral angle between the phenyl ring and the indole ring system is 15.7 (2)°, while that between the phenyl ring and the central pyridine ring is 46.3 (1)°. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O hydrogen bonding, forming an S(6) ring motif. In the crystal, mol-ecules are linked via pairs of N-H⋯N hydrogen bonds, forming inversion dimers with an R 2 (2)(16) ring motif. The crystal structure also features C-H⋯π and π-π inter-actions [centroid-centroid separation = 3.688 (1) Å].

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4645016PMC
http://dx.doi.org/10.1107/S2056989015018058DOI Listing

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