5-(4-Fluorophenyl)-2-methyl-3-methylsulfinyl-1-benzofuran

In the title compound, C16H13FO2S, the 4-fluorophenyl ring makes a dihedral angle of 38.75 (8)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds.

In the title compound, C 16 H 13 FO 2 S, the 4-fluorophenyl ring makes a dihedral angle of 38.75 (8) with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C-HÁ Á ÁO hydrogen bonds.

Experimental
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QK2019). Galal et al., 2009, Khan et al., 2005. These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003;Soekamto et al., 2003). As a part of our ongoing studies of the substituent effect on the solid state structures of 5-aryl-2-methyl-3-methylsulfinyl-1-benzofuran analogues, see: Choi et al. (2006Choi et al. ( , 2009, we report herein the crystal structure of the title compound. In the title molecule ( Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.011 (2) Å from the least-squares plane defined by the nine constituent atoms. The diheral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofurn fragment is 38.75 (8)°. In the crystal packing ( Fig. 2), molecules are linked by weak intermolecular C-H···O hydrogen bonds; the first one between a benzene H atom and the O atom of the sulfinyl group (Table 1; C5-H5···O2 i ), the second one between a methyl H atom of the methylsulfinyl group and the O atom of the sulfinyl group (Table 1; C16-H16B···O2 ii ).

Refinement
All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.95 Å for aryl and 0.98 Å for methyl H atoms. U iso (H) = 1.2U eq (C) for aryl and 1.5U eq (C) for methyl H atoms.
supplementary materials sup-2 Figures Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.

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.