2,2,2-Trifluoro-N-(2-iodophenyl)acetamide

The three F atoms in the title compound, C8H5F3INO, are disordered over two sets of sites [relative occupancies = 0.615 (14):0.385 (14)]. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming chains running along the c-axis direction. The dihedral angle between the ring and the amide group is 62.1 (3)°.


Comment
Aromatic compounds play an important role in the pharmaceutical and agrochemical industries as important intermediates. The fluorine atom has a strong electron withdrawing character and small atomic radius. Introduction of one or more F atoms can change the physiological activity, pharmacological activity and metabolic stability properties of the compound (Jeschke, 2004;Mueller, et al., 2007;Purser, et al., 2008). In our study, we report an aromatic compounds containing fluorine, 2,2,2-trifluoro-N-(2-iodophenyl)acetamide, which could be used in the synthesis of many bioactive compounds.
The crystal packing is stabilized by N1-H1···O1 hydrogen bond that connect molecules into chains running along the c direction.

Experimental
The title compound was synthesized according to the previously reported procedure (Konfink, et al., 2007).

Refinement
H atoms bond to N were located in a difference map and refined with N-H = 0.86 Å and U iso (H) = 1.2U eq (N) other H atoms attached to C were fixed geometrically and treated as riding with C-H = 0.96 Å (methyl) or 0.93 Å (aromatic) and with U iso (H) = 1.2U eq (aromatic) or U iso (H) = 1.5U eq (methyl).

2,2,2-Trifluoro-N-(2-iodophenyl)acetamide
Crystal data Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o 2 ) + (0.0324P) 2 + 3.0148P] where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.42 e Å −3 Δρ min = −0.54 e Å −3 Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 )
x y z U iso */U eq Occ. (