Crystal structures and anti­oxidant capacity of (E)-5-benz­yloxy-2-{[(4-chloro­phen­yl)imino]­meth­yl}phenol and (E)-5-benz­yloxy-2-({[2-(1H-indol-3-yl)eth­yl]iminium­yl}meth­yl)phenolate

The title Schiff base compounds, C(20)H(16)ClNO(2) (I) and C(24)H(22)N(2)O(2) (II), were synthesized via the condensation reaction of 2-amino-4-chloro­phenol for (I), and 2-(2,3-di­hydro-1H-indol-3-yl)ethan-1-amine for (II), with 4-benz­yloxy-2-hy­droxy­benzaldehyde. In both compounds, the configuration about the C=N imine bond is E. Neither mol­ecule is planar. In (I), the central benzene ring makes dihedral angles of 49.91 (12) and 53.52 (11)° with the outer phenyl and chloro­phenyl rings, respectively. In (II), the central benzene ring makes dihedral angles of 89.59 (9) and 72.27 (7)°, respectively, with the outer phenyl ring and the mean plane of the indole ring system (r.m.s. deviation = 0.011 Å). In both compounds there is an intra­molecular hydrogen bond forming an S(6) ring motif; an O—H⋯O hydrogen bond in (I), but a charge-assisted N(+)—H⋯O(−) hydrogen bond in (II). In the crystal of (I), mol­ecules are linked by C—H⋯π inter­actions, forming slabs parallel to plane (001). In the crystal of (II), mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers. The dimers are linked by C—H⋯O hydrogen bonds, C—H⋯π inter­actions and a weak N—H⋯π inter­action, forming columns propagating along the a-axis direction. The anti­oxidant capacity of the synthesized compounds was determined by cupric reducing anti­oxidant capacity (CUPRAC) for compound (I) and by 2,2-picrylhydrazyl hydrate (DPPH) for compound (II).