Synthesis, crystal structure and Hirshfeld surface analysis of the orthorhombic polymorph of 4-bromo-N-(4-bromobenzylidene)aniline

Abstract

The crystal structure of the title compound, C13H9Br2N [systematic name: (E)-N,1-bis(4-bromophenyl)methanimine], is a second polymorph (Form II) crystallizing in the orthorhombic space group Pccn. The first polymorph (Form I) crystallizes in the monoclinic space group P21/c [Bernstein & Izak (1975). J. Cryst. Mol. Struct. 5, 257–266; Marin et al. (2013). J. Mol. Struct. 1049, 377–385]. The molecule is disordered about an inversion center situated in the middle of the C=N bond, similar to the situation in the monoclinic polymorph: the C=N bond length is 1.243 (7) Å. In the crystal, molecules stack along the b-axis direction and are linked by C—H...π interactions. The interatomic contacts in the crystal for both polymorphs were studied by Hirshfeld surface analysis and have notable differences. The solid-state fluorescence spectrum of Form II shows an emission peak at ca 469 nm. The two-photon absorption coefficient measured from the open aperture Z-scan technique is 1.3 × 10 −11 m W−1, hence, Form II shows optical limiting behaviour.

Keywords

• crystal structure
• n-benzylideneaniline
• polymorphism
• hirshfeld surface
• fluorescence
• two-photon absorption