Synthesis, crystal structure and Hirshfeld surface analysis of the orthorhombic polymorph of 4-bromo-N-(4-bromobenzylidene)aniline
-
Published:2023-02-09
Issue:3
Volume:79
Page:146-150
-
ISSN:2056-9890
-
Container-title:Acta Crystallographica Section E Crystallographic Communications
-
language:
-
Short-container-title:Acta Cryst E
Author:
Subashini A.,
Ramamurthi K.,
Ramesh Babu R.,
Philip Reji,
Stoeckli-Evans HelenORCID
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.
Funder
University Grants Commission
Publisher
International Union of Crystallography (IUCr)
Subject
Condensed Matter Physics,General Materials Science,General Chemistry