title: Crystal structure of 4-bromo-N-(2-bromo-3-nitro-benz-yl)-2-nitro-naphthalen-1-amine.
abstract: In the title compound, C17H11Br2N3O4, the dihedral angle between the planes of the naphthalene system and the benzene ring is 52.86 (8)°. The nitro substituent and the attached naphthalene system are almost coplanar [dihedral angle = 5.6 (4)°], probably as a consequence of an intra-molecular N-H⋯O hydrogen bond with the amine group. The nitro substituent attached to the benzene ring is disordered over two sets of sites with occupancies of 0.694 (3) and 0.306 (3). The major component deviates significantly from the ring plane [dihedral angle = 53.6 (2)°]. In the crystal, the mol-ecules are linked into a three-dimensional array by extensive π-π inter-actions involving both the naphthalene and benzene rings [range of centroid-centroid distances = 3.5295 (16)-3.9629 (18) Å] and C-H⋯O inter-actions involving the methyl-ene H atoms and the phenyl-attached nitro group.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India.
authors.forename: Vijay P
authors.initials: VP
authors.lastname: Singh
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India.
authors.forename: Krishnan
authors.initials: K
authors.lastname: Venkateshwaran
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India.
authors.forename: Harkesh B
authors.initials: HB
authors.lastname: Singh
authors.affiliation: Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA.
authors.forename: Ray J
authors.initials: RJ
authors.lastname: Butcher
keywords: aryl­selenium compounds; crystal structure; hydrogen bonding; naphthalen-1-amine; photoluminescent seleno­spiro­cyclic compounds; π–π inter­actions