Hydrogen bonding in C-substituted nitroanilines: pi-stacked sheets of R4 4(20) and R4 4(28) rings in 2-cyano-4-nitroaniline.
In the title compound, C(7)H(5)N(3)O(2), 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 A, N...O = 3.022 (2) and 3.043 (2) A and N-H...O both 159 degrees ] and two N-H...N hydrogen bonds [H...N = 2.14 and 2.17 A, N...N = 2.990 (2) and 3.001 (2) A, and N-H...N = 162 and 158 degrees ]. The sheets are linked into a three-dimensional framework by a single aromatic pi-pi stacking interaction.
Glidewell
Christopher
C
School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland. cg@st-andrews.ac.uk
Low
John N
JN
Skakle
Janet M S
JM
Wardell
James L
JL