Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 3 (March 2013)

organic compounds

Acta Cryst. (2013). E69, o425    [ doi:10.1107/S1600536813004571 ]

A polymorph of 2,4-dinitro­phenyl­hydrazine

K. Amimoto and H. Nishiguchi

Abstract: The crystal structure of a previously unreported polymorph (form II) of 2,4-dinitro­phenyl­hydrazine (DNPH), C6H6N4O4, was determined at 90 K. The first polymorph (form I) is described in the monoclinic space group P21/c [Okabe et al. (1993). Acta Cryst. C49, 1678-1680; Wardell et al. (2006). Acta Cryst. C62, o318-320], whereas form II is in the monoclinic space group Cc. The mol­ecular structures in forms I and II are closely similar, with the nitro groups at the 2- and 4-positions being almost coplanar with the benzene ring [dihedral angles of 3.54 (1) and 3.38 (1)°, respectively in II]. However, their packing arrangements are completely different. Form I exhibits a herringbone packing motif, whereas form II displays a coplanar chain structure. Each chain in form II is connected to adjacent chains by the inter­molecular inter­action between hydrazine NH2 and 2-nitro groups, forming a sheet normal to (101). The sheet is stabilized by N-H...[pi] inter­actions.

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