(4-Fluorophenyl)(1H-pyrrol-2-yl)methanone

In the title molecule, C11H8FNO, the dihedral angle between the pyrrole and benzene rings is 49.16 (6)°. In the crystal, adjacent molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers.

Data collection: CrysAlis PRO (Oxford Diffraction,2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009  The chemistry of pyrrole compounds and biological activities of the related compounds have been extensively studied (Fischer & Orth, 1934;Mohamed et al., 2009). With the view of biological importance, the title compound was synthesized and its crystal structure is reported here.
Bond lengths and angles in the title compound ( Fig. 1) have normal values (Allen et al., 1987) and are comparable with the similar crystal structures solved earlier (English et al., 1980). The pyrrole and benzene rings are planar with maximum deviations of 0.004 (2) Å and -0.009 (2) Å, respectively. The two rings are not coplanar with the dihedral angle being 49.16 (6)°. The crystal packing is stabilized by N-H···O intermolecular interactions, generating centrosymmetric dimers (Fig. 2).

Experimental
Amide-phosphoryl complex was prepared by treating 1 equiv. of N,N-dimethyl-4-fluorobenzamide with 3 equiv. of POCl 3 at room temperature and stirred for 6 h. The above complex was treated with pyrrole in anhydrous 1,2-dichloroethane at 25°C and stirred for one hour and kept overnight. The resulting mixture was hydrolyzed using saturated sodium carbonate solution, followed by heating for 45 minutes to obtain the title compound. The title compound was extracted using 1,2-dichloroethane. Single crystals required for X-ray diffraction were obtained by slow evaporation of the methanolic solution of the compound.

Refinement
All H atoms were positioned geometrically and were treated as riding on their parent atoms, with d(N-H)= 0.86 Å and d(C-H) = 0.93 Å for aromatic, and with U iso (H) = 1.2U eq (C aryl , N).

Computing details
Data collection: CrysAlis PRO (Oxford Diffraction,2010); cell refinement: CrysAlis PRO (Oxford Diffraction,2010); data reduction: CrysAlis PRO (Oxford Diffraction,2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009    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.