2-Chloro-4-iodoaniline

The title dihaloaniline, C6H5ClIN, shows no significant hydrogen bonds nor the commonly observed I⋯I interactions in the crystal structure, although an amino group and an I atom are available for such contacts. The crystal structure is stabilized by weak interactions involving the amine functionality as donor group and N or halogen atoms as acceptors.

The title dihaloaniline, C 6 H 5 ClIN, shows no significant hydrogen bonds nor the commonly observed IÁ Á ÁI interactions in the crystal structure, although an amino group and an I atom are available for such contacts. The crystal structure is stabilized by weak interactions involving the amine functionality as donor group and N or halogen atoms as acceptors.
The asymmetric unit contains one molecule (Fig. 1). The N atom is not coplanar with the aromatic ring; H atoms of the amino group are also out of the halogenated benzene ring, but in the opposite direction to that of the N atom. So, the C(Ar)NH 2 group has a pyramidal shape. This is similar to the structure of aniline at 252 K (Fukuyo et al., 1982), 2-iodoaniline at 100 K (Parkin et al., 2005) and 4-iodoaniline at 203 K (Dey et al., 2003).
Despite the presence of amino, chloro and iodo groups, no classic interactions associated with them, such as hydrogen bonds, Cl···Cl, or I···I contacts were observed in the crystal structure of (I). Instead, weak interactions such as N-H···N, N-H···I, and N-H···Cl are found to provide stability to the crystal (Fig. 2).

Experimental
The compound was purchased from TCI America Laboratory Chemicals as colorless block crystals suitable for single-crystal X-ray diffraction measurement.

Refinement
H atoms were found in a difference map and those on the aromatic ring subsequently placed in idealized positions with C-H distances of 0.95 Å and isotropic displacement parameters equal to 1.2U eq of the carrier C atom. Amine H atoms H1N and H2N were refined freely but were restrained to converge to the same N-H bond lengths, with a standard deviation of 0.02 Å. Isotropic displacement parameters for H1N and H2N were computed as 1.5U eq (N1) supplementary materials sup-2 Figures   Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level (arbitrary spheres for the H atoms).  Geometric parameters (Å, °)