Phenyl(3-methyl-1-phenylsulfonyl-1H-indol-2-yl)methanone

In the title compound, C22H17NO3S, the N atom of the indole ring system deviates by 0.031 (3) Å from a least-squares plane fitted through all nine non-H ring atoms. The geometry around the S atom can be described as distorted tetrahedral. As a result of the electron-withdrawing character of the phenylsulfonyl groups, the N—Csp 2 bond lengths are longer than the typical mean value for N atoms with a planar configuration.

In the title compound, C 22 H 17 NO 3 S, the N atom of the indole ring system deviates by 0.031 (3) Å from a least-squares plane fitted through all nine non-H ring atoms. The geometry around the S atom can be described as distorted tetrahedral. As a result of the electron-withdrawing character of the phenylsulfonyl groups, the N-Csp 2 bond lengths are longer than the typical mean value for N atoms with a planar configuration.

Comment
The indole ring system is present in a number of natural products, many of which are found to possess anticancer, antimalarial and antihypertensive activities (Ma et al., 2001). Sulfonamide derivates are well known drugs and are used to control diseases caused by bacterial infections. Against this background and in order to obtain detailed information on molecular conformations in the solid state, X-ray study of the title compound was carried out.
X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The indole ring system is essentially planar with a mean deviation from a plane defined by the nine non-H ring atoms of 0.031 (3) Å for N. The sum of bond angles around N1 [348.4 (12)°] of the pyrrole ring is in accordance with sp 3 hybridization (Beddoes et al., 1986). The indole ring system makes dihedral angles of 61.7 (8) and 77.7 (8)°, respectively, with the benzene and phenyl rings.

Experimental
To a solution of N-(2-acetylphenyl)benzenesulfonamide (0.4 g, 1.45 mmol) in dry CH 3 CN (20 ml), K 2 CO 3 (0.6 g, 4.34 mmol), 2-bromo-1-phenylethanone (0.34 g, 1.70 mmol) were added. The reaction mixture was stirred at room temperature for 6 h under N 2 atmosphere. The solvent was removed and the residue was quenched with ice-water (50 ml), extracted with chloroform (3 × 10 ml) and dried (Na 2 SO 4 ). Removal of solvent followed by the residue was dissolved in CH 3 CN (20 ml), Concentrated HCl (3 ml) was added. The reaction mixture was then refluxed for 2 h. It was then poured over ice-water (50 ml), extracted with CHCl 3 (3 × 10 ml) and dried (Na 2 SO 4 ). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.

Refinement
All H atoms were fixed geometrically and allowed to ride on their parent C atoms, with C-H distances fixed in the range 0.93-0.97 Å with U iso (H) = 1.5U eq (C) for methyl H 1.2U eq (C) for other H atoms.
supplementary materials sup-2 Figures Fig. 1. The structure of showing the atom-numbering scheme and intramolecular hydrogen bond. Displacement ellipsoids are drawn at the 30% probability level.
Cell parameters from 5682 reflections a = 22.8120 (7)  as those based on F, and R-factors based on ALL data will be even larger.