Crystal structure of (E)-N1-[(anthracen-9-yl)methyl-idene]-N4-phenyl-benzene-1,4-di-amine.

Musheer Ahmad,Md Serajul Haque Faizi,Irina A Golenya,Ashanul Haque

doi:10.1107/s2056989016020612

Abstract

The title compound, C27H20N2, a Schiff base synthesized via a condensation reaction between anthracene-9-carbaldehyde and N-phenyl-p-phenyl-enedi-amine, crystallizes with three independent mol-ecules in the asymmetric unit. The three mol-ecules have slightly varying overall conformations, all having trans conformations with respect to the C=N bond. In the crystal, the packing features N-H⋯N hydrogen bonds, which connect mol-ecules into chains extending along the c-axis direction, inter-linked by C-H⋯π inter-actions (minimum H⋯Cg = 2.65 Å) into sheets lying parallel to (001).

Highlights

The title compound, C27H20N2, a Schiff base synthesized via a condensation reaction between anthracene-9-carbaldehyde and N-phenyl-p-phenylenediamine, crystallizes with three independent molecules in the asymmetric unit
Anthracene derivatives have been widely used in the field of anion recognition, metal ion fluorescent sensors, as well as pH
As part of our ongoing studies of Schiff bases (Faizi et al, 2016), we report on the synthesis and crystal structure of the title compound, (E)-N1-[(anthracen-9-yl)methylidene]N4-phenylbenzene-1,4-diamine, obtained from the condensation of 9-anthracenecarboxaldehyde with N-phenyl-pphenylenediamine

Summary

Chemical context

Anthracene derivatives have been widely used in the field of anion recognition, metal ion fluorescent sensors, as well as pH sensors 2002; Bernhardt et al 2001) because of their excellent photophysical properties and high fluorescence. The crystal structures of several anthracene derivatives have been reported previously for supramolecular photochemistry (Akiba et al, 1999; Yuan et al, 2004; Yamashita et al, 2005). As part of our ongoing studies of Schiff bases (Faizi et al., 2016), we report on the synthesis and crystal structure of the title compound, (E)-N1-[(anthracen-9-yl)methylidene]N4-phenylbenzene-1,4-diamine, obtained from the condensation of 9-anthracenecarboxaldehyde with N-phenyl-pphenylenediamine.

Structural commentary

Supramolecular features

Database survey

Synthesis and crystallization

Findings

Refinement