Abstract

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 mol­ecular structure is stabilized by an intra­molecular O—H⋯O hydrogen bonding, forming an S(6) ring motif. In the crystal, mol­ecules 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 inter­actions [centroid–centroid separation = 3.688 (1) Å].

Highlights

  • The central pyridine ring is inclined to the indole ring system by 43.7 (1)

  • The molecular structure is stabilized by an intramolecular O—H O hydrogen bonding, forming an S(6) ring motif

  • Cg3 and Cg4 are the centroids of the C1–C6 and C16–C21 rings, respectively

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Summary

Crystal data

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 molecular structure is stabilized by an intramolecular O—H O hydrogen bonding, forming an S(6) ring motif. Molecules are linked via pairs of N—H N hydrogen bonds, forming inversion dimers with an R22(16) ring motif. The crystal structure features C—H and – interactions [centroid–centroid separation = 3.688 (1) Å]

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