The growth of crystals suitable for X-ray crystallography has resulted in the first complete structural characterizations of two iminoiodinanes PhINTs, 1, and MesINTs, 2 (Mes = 2,4,6-Me(3)C(6)H(2); Ts = SO2C6H4-4-Me). Two different types of structures were observed. They consist of monomeric ArINTs units, bridged either by I ... N interactions 2.482(2) Angstrom in length in the case of 1 or by long (2.857(4) Angstrom) I ... O interactions in the case of 2. The structural parameters of 1 and 2 show that the intramolecular I-N distance is consistent with a single bond and that the structures are probably best represented by resonance forms that feature negative charge at the oxygens and positive charge at iodine. Compounds 1 and 2 are closely related to the iodosylaryls, ArIO, and their structures lend further weight to the proposed associated structures of these oxygen derivatives which are thought to have a backbone composed of an -I-O ... I-O- bridging array. The structure of TripICl(2) (Trip = 2,4,6-i-Pr3C6H2), 3, shows that the iodine center has T-shaped geometry and that the molecules are very weakly associated in the solid state through a long I ... Cl interaction of 3.490(2) Angstrom. Crystal data at 130 K with Mo K alpha (lambda = 0.710 73 Angstrom) radiation : 1, C13H12INO2S, a = 11.519(2) Angstrom, b = 7.687(2) Angstrom, c = 15.181(4) Angstrom, beta = 104.88(2)degrees, Z = 4, monoclinic, space group P2(1)/c, R = 0.021, for 2537 (I > 2 sigma(I)) data; 2, C16H18INO2S, a = 9.203(2) Angstrom, b = 17.010(7) Angstrom, c = 19.888(5) Angstrom, Z = 8, orthorhombic, space group Pbca, R = 0.033 for 2642 (I > 2 sigma(I)) data; 3, C16H23Cl2I, a = 8.485(2) Angstrom, b = 17.308(3) Angstrom, c = 11.880(3) Angstrom, beta = 101.75(2)degrees, Z = 4, monoclinic, space group P2(1)/c, R = 0.046 for 3314 (I > 2 sigma(I)) data.