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.