Abstract
The title Schiff base compounds, C20H16ClNO2 (I) and C24H22N2O2 (II), were synthesized via the condensation reaction of 2-amino-4-chloro-phenol for (I), and 2-(2,3-di-hydro-1H-indol-3-yl)ethan-1-amine for (II), with 4-benz-yloxy-2-hy-droxy-benzaldehyde. In both compounds, the configuration about the C=N imine bond is E. Neither mol-ecule is planar. In (I), the central benzene ring makes dihedral angles of 49.91 (12) and 53.52 (11)° with the outer phenyl and chloro-phenyl 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 intra-molecular 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), mol-ecules are linked by C-H⋯π inter-actions, forming slabs parallel to plane (001). In the crystal of (II), mol-ecules 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 inter-actions and a weak N-H⋯π inter-action, forming columns propagating along the a-axis direction. The anti-oxidant capacity of the synthesized compounds was determined by cupric reducing anti-oxidant capacity (CUPRAC) for compound (I) and by 2,2-picrylhydrazyl hydrate (DPPH) for compound (II).
Highlights
The title Schiff base compounds, C20H16ClNO2 (I) and C24H22N2O2 (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-2hydroxybenzaldehyde
In the crystal of (II), molecules are linked by pairs of N—HÁ Á ÁO hydrogen bonds, forming inversion dimers
The dimers are linked by C—HÁ Á ÁO hydrogen bonds, C—HÁ Á Á interactions and a weak N—HÁ Á Á interaction, forming columns propagating along the a-axis direction
Summary
Schiff bases of the general type RR0C NR00 exhibit a wide structural diversity and have found a wide range of applications (Jia & Li, 2015). Schiff base derivatives are a biologically versatile class of compounds possessing diverse activities, such as anti-oxidant (Haribabu et al, 2015, 2016), anti-inflammatory (Alam et al, 2012), antianxiety, antidepressant (Jubie et al, 2011), anti-tumour, antibacterial, and fungicidal properties (Refat et al, 2008; Kannan & Ramesh, 2006) They can be used as potential materials for optical memory and switch devices (Zhao et al, 2007). E74, 478–482 is the presence of an azomethine group linked by an -methylene bridge, which can act as hydrogen-bond acceptors In view of this interest we have synthesized the title compounds, (I) and (II), and report on their crystal structures. In the crystal of (I), molecules are linked by C—HÁ Á Á
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