Crystal structures and anti-oxidant capacity of (E )-5-benz-yloxy-2-{[(4-chloro-phen-yl)imino]-meth-yl}phenol and (E )-5-benz-yloxy-2-({[2-(1H -indol-3-yl)eth-yl]iminium-yl}meth-yl)phenolate

Acta Crystallographica. Section E, Crystallographic Communications
Nadir GhichiHocine Merazig

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-...Continue Reading

References

Nov 14, 2006·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Liyan ZhaoShimei Jiang
Nov 21, 2007·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Moamen S RefatAhmed S Ahmed
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jan 28, 2009·Acta Crystallographica. Section D, Biological Crystallography·Anthony L Spek
Oct 14, 2014·Acta Crystallographica. Section E, Structure Reports Online·Nadir GhichiHocine Merazig
Jan 2, 2015·Acta Crystallographica. Section E, Structure Reports Online·Nadir GhichiHocine Merazig
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Feb 13, 2016·Acta Crystallographica. Section E, Crystallographic Communications·Nadir GhichiHocine Merazig
Apr 7, 2016·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Colin R GroomSuzanna C Ward

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