4-Iodo-2-methylaniline

In the molecule of the title compound, C7H8IN, the methyl C, I and N atoms lie in the benzene ring plane. In the crystal structure, intermolecular N—H⋯N hydrogen bonds link the molecules in a stacked arrangement along the a axis.

In the molecule of the title compound, C 7 H 8 IN, the methyl C, I and N atoms lie in the benzene ring plane. In the crystal structure, intermolecular N-HÁ Á ÁN hydrogen bonds link the molecules in a stacked arrangement along the a axis.

Comment
The title compound, (I), contains amino and halogen groups, which can react with different groups to prepare various function organic compounds. It is a kind of aromatic organic intermediate that can be used for many fields such as aromatic conductive polymer, organometallic chemistry etc. (Kajigaeshi et al., 1988). We report herein its crystal structure.
In the molecule of (I), (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The atoms I, N and C7 lie in the benzene ring plane.
In the crystal structure, intermolecular N-H···N hydrogen bonds (Table 1) link the molecules stacked along the a axis, (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental
The title compound, (I), was prepared by the literature method (Kajigaeshi et al., 1988). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in hexane (20 ml) and evaporating the solvent slowly at room temperature for about 7 d.

Refinement
H atoms were positioned geometrically, with N-H = 0.86 Å (for NH 2 ) and C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with U iso (H) = xU eq (C,N), where x = 1.5 for methyl H, and x= 1.2 for all other H atoms. Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )