2-(2-Amino-4-nitro-phen-yl)-7-nitro-4H-3,1-benzoxazin-4-one

Edward R T Tiekink; James L Wardell

doi:10.1107/S1600536814000609

2-(2-Amino-4-nitro-phen-yl)-7-nitro-4H-3,1-benzoxazin-4-one

Acta Crystallogr Sect E Struct Rep Online. 2014 Jan 18;70(Pt 2):o158-9. doi: 10.1107/S1600536814000609. eCollection 2014 Feb 1.

Authors

Edward R T Tiekink¹, James L Wardell²

Affiliations

¹ Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.
² Fundação Oswaldo Cruz, Instituto de Tecnologia em, Fármacos-Farmanguinhos, R. Sizenando Nabuco, 100, Manguinhos 21041-250, Rio de Janeiro, RJ, Brazil ; Chemistry Department, University of Aberdeen, Old Aberdeen AB24 3UE, Scotland.

Abstract

In the title compound, C14H8N4O6, the benzoxazin-4-one fused-ring system (r.m.s. deviation = 0.018 Å) is coplanar with the attached benzene ring [dihedral angle = 0.81 (4)°], there being an intra-molecular N-H⋯N hydrogen bond between them. Each nitro group is twisted out of the plane of the attached benzene ring [O-N-C-C torsion angles = 167.94 (11) and 170.38 (11)°]. In the crystal, amine-nitro N-H⋯O hydrogen bonds lead to centrosymmetric dimeric aggregates that are connected into a three-dimensional architecture by oxazin-yl-nitro C-H⋯O and π-π inter-actions [inter-centroid distance between the oxazinyl and terminal benzene rings = 3.5069 (7) Å].