Crystal structures and Hirshfeld surface analyses of (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-phenyl-diazene, (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(4-methyl-phen-yl)diazene, (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(4-meth-oxy-phen-yl)diazene and (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(3-methyl-phen-yl)diazene.

Abstract

The crystal structures and Hirshfeld surface analyses of four similar azo compounds are reported. (E)-1-[1-(4-tert-Butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-phenyl-diazene, C18H18Cl2N2, (I), and (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(4-methyl-phen-yl)diazene, C19H20Cl2N2, (II), crystallize in the monoclinic space group C2/c with Z = 8, and (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(4-meth-oxy-phen-yl)diazene, C19H20Cl2N2O, (III), in the monoclinic space group P21/c with Z = 4. (E)-1-[1-(4-tert-Butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(3-methyl-phen-yl)diazene, C19H20Cl2N2, (IV), crystallizes in the triclinic space group P with Z = 4 and comprises two mol-ecules (A and B) in the asymmetric unit. In the crystal structures of (I) and (II), mol-ecules are linked by C-H⋯π and C-Cl⋯π inter-actions, forming layers parallel to (02), while mol-ecules of (III) are linked by C-H⋯O contacts, C-H⋯π and C-Cl⋯π inter-actions forming layers parallel to (02). The stability of the mol-ecular packing is ensured by van der Waals forces between these layers. In the crystal structure of (IV), mol-ecules are linked by C-H⋯π and C-Cl⋯π inter-actions, forming a tri-periodic network.