Crystal structure of 4-bromo-N-(2- bromo-3-nitrobenzyl)-2-nitronaphthalen- 1-amine Vijay P. Singh, a Krishnan Venkateshwaran, a Harkesh B. Singh a and Ray J. Butcher b * a Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India, and b Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA. *Correspondence e-mail: rbutcher99@yahoo.com Received 27 June 2014; accepted 25 July 2014 Edited by E. R. T. Tiekink, University of Malaya, Malaysia In the title compound, C 17 H 11 Br 2 N 3 O 4 , 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—HO 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 molecules are linked into a three- dimensional array by extensive – interactions involving both the naphthalene and benzene rings [range of centroid– centroid distances = 3.5295 (16)–3.9629 (18) A ˚ ] and C— HO interactions involving the methylene H atoms and the phenyl-attached nitro group. Keywords: crystal structure; naphthalen-1-amine; – interactions; hydrogen bonding; arylselenium compounds; photoluminescent seleno- spirocyclic compounds. CCDC reference: 1015963 1. Related literature For the role of secondary interactions in stabilizing organo- selenium compounds, see; Singh et al. (2010, 2012); Mugesh & Singh (2000). For the isolation of novel photoluminescent selenospirocyclic compounds via intermolecular C—C bond formation, see: Singh et al. (2011). 2. Experimental 2.1. Crystal data C 17 H 11 Br 2 N 3 O 4 M r = 481.11 Triclinic, P 1 a = 8.3675 (4) A ˚ b = 8.5812 (5) A ˚ c = 12.2691 (5) A ˚ = 76.973 (4) = 81.053 (4) = 76.302 (5) V = 829.00 (8) A ˚ 3 Z =2 Mo K radiation = 4.92 mm 1 T = 123 K 0.44 0.32 0.12 mm 2.2. Data collection Agilent Xcalibur (Ruby, Gemini) diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T min = 0.345, T max = 1.000 12164 measured reflections 6700 independent reflections 4118 reflections with I >2(I) R int = 0.033 2.3. Refinement R[F 2 >2(F 2 )] = 0.053 wR(F 2 ) = 0.129 S = 1.02 6700 reflections 246 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Á max = 1.04 e A ˚ 3 Á min = 0.77 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ , ). D—HA D—H HA DA D—HA N1—H1NO2 0.84 (3) 1.91 (3) 2.624 (3) 141 (3) C12—H12BO4A i 0.99 2.54 3.532 (4) 177 C12—H12BO4B i 0.99 2.61 3.462 (8) 144 Symmetry code: (i) x 1; y; z. Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 2012). Acknowledgements RJB acknowledges the NSF MRI program (grant No. CHE- 0619278) for funds to purchase an X-ray diffractometer. data reports o960 Singh et al. doi:10.1107/S160053681401719X Acta Cryst. (2014). E70, o960–o961 ISSN 1600-5368