Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E )-2-[(E )-2,6-di-chloro-benzyl-idene]hydrazin-1-yl-idene}meth-yl)-6-meth-oxy-phenol and 4-bromo-2-({(E )-2-[(E )-2,6-di-chloro-benzyl-idene]hydrazin-1-yl-idene}meth-yl)phenol

Acta Crystallographica. Section E, Crystallographic Communications
Rohit B ManawarEdward R T Tiekink

Abstract

Each of the title dis-symmetric di-Schiff base compounds, C15H12Cl2N2O2 (I) and C14H9BrCl2N2O (II), features a central azo-N-N bond connecting two imine groups, each with an E-configuration. One imine bond in each mol-ecule connects to a 2,6-di-chloro-benzene substituent while the other links a 2-hydroxyl-3-meth-oxy-substituted benzene ring in (I) or a 2-hydroxyl-4-bromo benzene ring in (II). Each mol-ecule features an intra-molecular hydroxyl-O-H⋯N(imine) hydrogen bond. The C-N-N-C torsion angles of -151.0 (3)° for (I) and 177.8 (6)° (II) indicates a significant twist in the former. The common feature of the mol-ecular packing is the formation of supra-molecular chains. In (I), the linear chains are aligned along the a-axis direction and the mol-ecules are linked by meth-oxy-C-H⋯O(meth-oxy) and chloro-benzene-C-Cl⋯π(chlorobenzene) inter-actions. The chain in (II) is also aligned along the a axis but, has a zigzag topology and is sustained by Br⋯O [3.132 (4) Å] secondary bonding inter-actions. In each crystal, the chains pack without directional inter-actions between them. The non-covalent inter-actions are delineated in the study of the calculated Hirshfeld surfaces. Dispersion forces make the most significant contributions to...Continue Reading

References

Dec 12, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Tirtha MukherjeeAsit R Sarkar
May 31, 2013·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Simon ParsonsTrixie Wagner
Jul 11, 2013·The Journal of Antibiotics·Hossein NaeimiMehdi Amouheidari
Apr 12, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Ryan M Clarke, Tim Storr
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Mar 15, 2019·Acta Crystallographica. Section E, Crystallographic Communications·Sang Loon TanEdward R T Tiekink
Oct 23, 2019·Acta Crystallographica. Section E, Crystallographic Communications·Rohit B ManawarEdward R T Tiekink

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