Crystal structure of (2-methyl-1-phenylsulfonyl-1H-indol-3-yl)(phenyl)methanone

In the title compound, the indole ring system makes the dihedral angles of 84.89 (7) and 57.32 (5)° with the phenyl rings. In the crystal, molecules are linked by C—H⋯O hydrogen bonds.


Chemical context
In a continuation of our studies on indole derivatives, which possess various biological activities such as antihepatitis B virus (Chai et al., 2006) and antibacterial (Nieto et al., 2005) etc, we herein report the synthesis and the crystal structure of the title compound, (I).

Figure 1
The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Synthesis and crystallization
To a solution of benzoyl chloride (1.55 g, 11.07 mmol) in dry DCM (25 ml), SnCl 4 (2.88 g, 10.10 mmol) at 273 K was added dropwise. To this, phenylsulfonyl-1H-indole (2 g, 7.38 mmol) in dry DCM (10 ml) was added dropwise (5 min) and stirred for 30 min at the same temperature. After completion of the reaction (monitored by TLC), it was poured over ice-water (50 ml) and extracted with saturated aqueous NaHCO 3 (2 Â 30 ml) and brine (2 Â 30 ml), dried (Na 2 SO 4 ) and concentrated under reduced pressure. Then, the crude product was crystallized from methanol to afford single crystals of the title compound suitable for X-ray diffraction.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms for C aromatic and C methyl were positioned geometrically and refined using a riding model, with C-H = 0.93 and 0.97 Å , respectively with U iso (H) = 1.5U eq (C) for methyl H atoms and 1.2U eq (C) for other H atoms.

(2-Methyl-1-phenylsulfonyl-1H-indol-3-yl)(phenyl)methanone
Crystal data Orthorhombic, P2 1 2 1 2 1 Hall symbol: P 2ac 2ab a = 8.9989 (7)  Extinction correction: SHELXL97 (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.0039 (8) Absolute structure: Flack (1983), 2109 Friedel pairs Absolute structure parameter: −0.01 (7) 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.