Methyl 4-(trifluoromethyl)-1H-pyrrole-3-carboxylate

In the title compound, C7H6F3NO2, all the non-H atoms except for one of the F atoms lie on a crystallographic mirror plane. In the crystal, the molecules are linked into inversion dimers by pairs of C—H⋯F interactions, forming R 2 2(10) loops. These dimers are connected into C(6) chains along [001] through N—H⋯O hydrogen bonds. Aromatic π–π stacking interactions [centroid-centroid separation = 3.8416 (10) A°] connect the molecules into a three-dimensional network.

In the title compound, C 7 H 6 F 3 NO 2 , all the non-H atoms except for one of the F atoms lie on a crystallographic mirror plane. In the crystal, the molecules are linked into inversion dimers by pairs of C-HÁ Á ÁF interactions, forming R 2 2 (10) loops. These dimers are connected into C(6) chains along [001] through N-HÁ Á ÁO hydrogen bonds. Aromaticstacking interactions [centroid-centroid separation = 3.8416 (10) A ] connect the molecules into a three-dimensional network.

Comment
Pyrrole derivatives are given considerable attention due to their synthetic importance and their extensive use in drug discovery (Toja et al., 1987) and pharmacological activity such as anti-inflammatory (Muchowski et al., 1985), cytotoxicity (Dannhardt et al., 2000), in vitro cytotoxic activity against solid tumour models (Burnham et al., 1998), antitumour agents (Krowicki et al., 1988]) etc. As part of our studies in this area, the title compound was synthesized and its structure determined.
The reaction mixture was stirred for 15 min. Toluenesulfonylmethyl isocyanide (TosMIC, 0.01 mol) was added to the reaction mixture and the mixture was heated to 50°C for 2 h. Reaction was monitored by TLC. Ethyl acetate was added to the mixture. Sodium hydride was quenched by using saturated solution of ammonium chloride and the organic layer was separated, dried and concentrated. The crude compound was purified by column chromatography using petroleum ether / ethyl acetate (7:3) as eluent to give the title compound as a colorless solid.
Colourless prisms were obtained from slow evapouration of the solution of the compound in a mixture of petroleum ether/ethyl acetate (7:3).

Refinement
The H atom of the NH group was located in a difference map and later refined freely. The other H atoms were positioned with idealized geometry using a riding model with C-H = 0.93-0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the U eq of the parent atom).

Computing details
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).    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 > σ(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.