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.

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??(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).

SUBMITTER: Manawar RB 

PROVIDER: S-EPMC7274017 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature