Crystal structure of methyl (2Z)-3-(4-chlorophenyl)-2-[(3-methyl-1H-indol-1-yl)methyl]prop-2-enoate

In the title indole derivative, the chlorophenyl ring is almost perpendicular to the indole moiety, making a dihedral angle of 87.59 (6)°. In the crystal, molecules are linked via C—H⋯π interactions, forming C(9) chains along the [10] direction.


Chemical context
Indole derivatives inhibit hepatitis C virus replication through induction of pro-inflammatory cytokines (Lee et al., 2015) and these derivatives act as a new anti-hepatitis C virus agents (Andreev et al., 2015). These derivatives also act as potential mushroom tyrosinase inhibitors (Ferro et al., 2015). Indole derivatives also exhibit anti-proliferative (Parrino et al., 2015), anti-inflammatory (Chen et al., 2015) and anti-tumor (Ma et al., 2015) activities. In view of the many interesting applications of indole derivatives, we synthesized the title compound and report herein on its crystal structure.

Supramolecular features
In the crystal, C-HÁ Á Á interactions link the molecules, forming C(9) chains propagating along [101]; see The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.   Table 1 Hydrogen-bond geometry (Å , ).

Figure 3
The molecular packing of the title compound, viewed along the b axis. C-HÁ Á Á interactions (Table 1)

Synthesis and crystallization
Substituted (Z)-methyl-2-(bromomethyl)-3-phenylacrylate (1 mmol), tetra-butyl-ammonium bromide (0.5 mmol), and 50% NaOH (20 ml) were added to a solution of 3-methyl indole (1 mmol) in benzene (55 ml). The mixture was stirred vigorously at room temperature for 5-6 h. The organic layer was separated, washed with water and dried over MgSO 4 . The solvent was evaporated under reduced pressure (yield: 70%). Suitable crystals were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.

Methyl (2Z)-3-(4-chlorophenyl)-2-[(3-methyl-1H-indol-1-yl)methyl]prop-2-enoate
Crystal data 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.