Crystal structure of 5-(5-chloro-2-hydroxybenzoyl)-2-(2-methyl-1H-indol-3-yl)nicotinonitrile

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].

5-(2-Hydroxybenzoyl)-2-(1H-indol-3-yl)pyridine-3-carbonitrile

“…The C-N distances range from 1.345 (2) to 1.370 (2) Å , and are in good agreement with the related reported values (Vishnupriya et al, 2014). The C14-O1 and C21-N3 bond lengths are 1.2347 (14) Å and 1.1413 (16) Å , respectively, in agreement with values reported by Vimala et al (2015), confirming the presence of double and triple bonds. The pyridine ring (C9/N2/ C10-C13) is in an antiperiplanar (Àap) orientation with the indole ring system (C1/N1/ C2-C8) and in an antiperiplanar (+ap) orientation with the hydroxyphenyl ring (C15-C20), as evidenced by the torsion angles C7-C8-C9-C13 = À163.54 (11) and C10-data reports C11-C14-C15 = 155.15 (11) , respectively.…”