(Z)-3-(1-Chloroprop-1-enyl)-2-methyl-1-phenylsulfonyl-1H-indole

In the title compound, C18H16ClNO2S, the indole ring system forms a dihedral angle of 75.07 (8)° with the phenyl ring. The molecular structure is stabilized by a weak intramolecular C—H⋯O hydrogen bond. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming a chain along [10-1]. C—H⋯π interactions are also observed, leading to a three-dimensional network.

In the title compound, C 18 H 16 ClNO 2 S, the indole ring system forms a dihedral angle of 75.07 (8) with the phenyl ring. The molecular structure is stabilized by a weak intramolecular C-HÁ Á ÁO hydrogen bond. In the crystal, molecules are linked by weak C-HÁ Á ÁO hydrogen bonds, forming a chain along [101]. C-HÁ Á Á interactions are also observed, leading to a threedimensional network.

Comment
The indole derivatives are known to exhibit anti-bacterial and anti-tumour activities (Okabe & Adachi, 1998;Schollmeyer et al., 1995). We herein report the crystal structure of the title compound (I), (Fig. 1). The geometric parameters of (I) are comparable with the reported similar structures (Chakkaravarthi et al., 2007(Chakkaravarthi et al., , 2008. The phenyl ring forms a dihedral angle of 75.07 (8)° with the indole ring system. The five-membered (N1/C7/C12-C14) and sixmembered (C7-C12) rings in the indole ring system are planar, with a dihedral angle of 0.38 (9)° between these rings.
Removal of the solvent followed a column chromatographic purification (Silica gel; hexane-ethyl acetate, 95:5) afforded the title compound, suitable for X-Ray diffraction quality crystals.

Refinement
H atoms were positioned geometrically and refined using riding model, with C-H = 0.93 Å and U iso (H) = 1.2U eq (C) for CH, and C-H = 0.96 Å and U iso (H) = 1.5U eq (C) for CH 3 .

Computing details
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008  The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.   Special details 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.