Crystal structure of methyl (E)-2-(1-methyl-2-oxoindolin-3-ylidene)acetate

Abstract

The title compound, C12H11NO3, is essentially planar, with the mean plane of the acetate side chain [–C—C(=O)—O—C] being inclined to the mean plane of the indole ring system by 12.49 (7)°. The five- and six-membered rings of the indole group are almost coplanar, making a dihedral angle of 1.76 (8)°. The conformation about the C=C bond is E and there is an intramolecular C—H...O hydrogen bond present. In the crystal, molecules are linked by pairs of C—H...O hydrogen bonds forming inversion dimers, with an R22(16) ring motif. The dimers are linked by a second pair of C—H...O hydrogen bonds, enclosing R22(16) ring motifs, forming ribbons lying parallel to (-114). The ribbons are linked via C—H...π interactions, forming a three-dimensional structure.

Keywords

• crystal structure
• indole
• 3-substituted indoles
• C—H...O hydrogen bonds
• C—H...π interactions
• π–π stacking interactions