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Each of the title dis-symmetric di-Schiff base compounds, C 15 H 12 Cl 2 N 2 O 2 (I) and C 14 H 9 BrCl 2 N 2 O (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 the identified inter-molecular inter-actions in each of (I) and (II).

acta crystallographica. section e, crystallographic communications

Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol