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. 2001 Aug;57(Pt 8):942-5.
doi: 10.1107/s0108270101007053. Epub 2001 Aug 9.

Triclinic and orthorhombic polymorphs of 2-iodo-4-nitroaniline: interplay of hydrogen bonds, nitro...I interactions and aromatic pi-pi-stacking interactions

S A McWilliam  1 , J M Skakle, J N Low, J L Wardell, S J Garden, A C Pinto, J C Torres, C Glidewell
Affiliations

Triclinic and orthorhombic polymorphs of 2-iodo-4-nitroaniline: interplay of hydrogen bonds, nitro...I interactions and aromatic pi-pi-stacking interactions

S A McWilliam et al. Acta Crystallogr C. 2001 Aug.

Abstract

In the triclinic polymorph of 2-iodo-4-nitroaniline, C(6)H(5)IN(2)O(2), space group P-1, the molecules are linked by paired N-H...O hydrogen bonds into C(8)[R(2)(2)(6)] chains of rings. These chains are linked into sheets by nitro...I interactions, and the sheets are pairwise linked by aromatic pi-pi-stacking interactions. In the orthorhombic polymorph, space group Pbca, the molecules are linked by single N-H...O hydrogen bonds into spiral C(8) chains; the chains are linked by nitro...O interactions into sheets, each of which is linked to its two immediate neighbours by aromatic pi-pi-stacking interactions, so producing a continuous three-dimensional structure.

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