Research Article: 2-Amino-4-nitro­phenol–1-(2,4,6-trihy­droxy­phen­yl)ethanone (1/1)

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Can Kocabıyık, Hümeyra Paşaoğlu, Taşkın Basılı, Erbil Ağar.


In the title compound, C6H6N2O3·C8H8O4, the 2-amino-4-nitro­phenol (ANP) and 1-(2,4,6-trihy­droxy­phen­yl)ethanone (THA) mol­ecules are both nearly planar, with r.m.s. deviations of 0.0630 and 0.0313 Å, respectively. The angle between the least-squares planes of THA and ANP is 48.99 (2)°. In THA, an intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds lead to the formation of a three-dimensional network. There are also inter­molecular π–π inter­actions between the benzene rings of ANP–ANP and of THA–THA mol­ecules, with centroid–centroid distances of 3.5313 (14) and 3.8440 (16) Å, respectively. Weak C—O⋯π and N—O⋯π inter­actions also occur.

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For the use of nitro­aromatics as inter­mediates in explosives, dyestuffs, pesticides and organic synthesis, see: Yan et al. (2006 ▶). For the occurrence of nitro­aromatics in industrial wastes and as direct pollutants in the environment, see: Yan et al. (2006 ▶); Soojhawon et al. (2005 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Tanak et al. (2009 ▶, 2010 ▶); Ali et al. (2008 ▶); Bi et al. (2009 ▶); Garden et al. (2004 ▶); Serdiuk et al. (2011 ▶).