Hydrogen bonding in C-substituted nitroanilines: n-stacked sheets of R 4 4(20) and R 4 4(28) rings in 2-cyano-4-nitroaniline

C. Glidewell, Janet Mabel Scott Skakle, J. L. Wardell

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4 Citations (Scopus)


In the title compound, C7H5N3O2, which crystallizes with Z' = 2 in space group P2(1)/c, the two independent molecules both exhibit positional disorder, with refined site-occupancy factors of 0.947 (2) and 0.053 (2) for the major and minor components, respectively. The major components have polarized molecular electronic structures. The two major components are linked into sheets of alternating R-4(4)(20) and R-4(4)(28) rings by two N - H...O hydrogen bonds [H...O = 2.18 and 2.21 Angstrom, N...O = 3.022 (2) and 3.043 (2) Angstrom and N - H...O both 159degrees] and two N - H...N hydrogen bonds [H...N = 2.14 and 2.17 Angstrom, N...N = 2.990 (2) and 3.001 (2) Angstrom, and N - H...N = 162 and 158degrees]. The sheets are linked into a three-dimensional framework by a single aromatic pi-pi stacking interaction.

Original languageEnglish
Pages (from-to)o35-o37
Number of pages3
JournalActa Crystallographica Section C, Crystal Structure Communications
Publication statusPublished - 2004



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