Received 25 January 2013
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 interactions.
For the use of DNPH for the identification of a carbonyl group, see: Brady & Elsmie (1926); Williamson et al. (2006). For the crystal structure of the first polymorph of DNPH, see: Okabe et al. (1993); Wardell et al. (2006).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2226 ).
This work was partially supported by a Grant-in-Aid for Young Scientists (B) (23700956) and a Grant-in-Aid for Scientific Research (C) (22300272) from the Japan Society for the Promotion of Science (JSPS). The data collection was performed at the Natural Science Center for Basic Research and Development (N-BARD), Hiroshima University.
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