Acta Cryst. (2009). E65, o1052-o1053  [ doi:10.1107/S1600536809011088 ]

3,3',5,5'-Tetranitrobiphenyl

N. Hammond, P. Carvalho, Y. Wu and M. A. Avery

Abstract: The title compound, C₁₂H₆N₄O₈, is a biphenyl system that was synthesized as a building block for a new series of antimalarial compounds. The aromatic rings are oriented at a dihedral angle of 45.5 (2)°, and intermolecular short OO contacts form a chain along the b axis. The strength of the interactions involved in this chain cause one of the rings to be slightly distorted, with the torsion angle between the nitro groups being 23.4 (2)°, whereas, in the other ring, both nitro systems are parallel, forming an angle of 9.6 (2)° with the plane of the aromatic ring to which they are bound. Furthermore, the three ring C atoms around the ring-ring linkage belong to a plane inclined by 4.5 (1)° in relation to the plane containing the other three C atoms, i.e. (NO₂-)C-C-C(NO₂). This distortion of the ring causes uncommonly short intermolecular OO [3.038 (2) Å] and OC [3.000 (4) and 3.214 (1) Å] contacts.

Online 18 April 2009

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