(E )-2-{[(2-Amino-phen-yl)imino]-meth-yl}-5-(benz-yl-oxy)phenol and (Z )-3-benz-yl-oxy-6-{[(5-chloro-2-hy-droxy-phen-yl)amino]-methyl-idene}cyclo-hexa-2,4-dien-1-one

Acta Crystallographica. Section E, Crystallographic Communications
Nadir GhichiHocine Merazig

Abstract

The title Schiff base compounds, C20H18N2O2 (I) and C20H16ClNO3 (II), were synthesized from 4-benz-yloxy-2-hy-droxy-benzaldehyde by reaction with 1,2-di-amino-benzene for (I), and condensation with 2-amino-4-chloro-phenol for (II). Compound (I) adopts the enol-imine tautomeric form with an E configuration about the C=N imine bond. In contrast, the o-hy-droxy Schiff base (II), is in the keto-imine tautomeric form with a Z configuration about the CH-NH bond. Neither mol-ecule is planar. In (I), the central benzene ring makes dihedral angles of 46.80 (10) and 78.19 (10)° with the outer phenyl-amine and phenyl rings, respectively, while for (II), the corresponding angles are 5.11 (9) and 58.42 (11)°, respectively. The mol-ecular structures of both compounds are affected by the formation of intra-molecular contacts, an O-H⋯N hydrogen bond for (I) and an N-H⋯O hydrogen bond for (II); each contact generates an S(6) ring motif. In the crystal of (I), strong N-H⋯O hydrogen bonds form zigzag chains of mol-ecules along the b-axis direction. Mol-ecules are further linked by C-H⋯π inter-actions and offset π-π contacts and these combine to form a three-dimensional network. The density functional theory (DFT) optimized structure of compound (...Continue Reading

References

Nov 28, 2006·The Journal of Physical Chemistry. B·Spyros D ChatziefthimiouIrene M Mavridis
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jan 1, 2008·Acta Crystallographica. Section E, Structure Reports Online·Hoong-Kun FunHasan Zargoshi
Nov 18, 2011·Acta Crystallographica. Section E, Structure Reports Online·Hoong-Kun FunD Jagadeesh Prasad
Jun 2, 2012·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Yuxi SunCheng Yu
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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Citations

May 7, 2021·Acta Crystallographica. Section E, Crystallographic Communications·Shaaban K MohamedElham A Al-Taifi

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Methods Mentioned

BETA
X-ray
NMR

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