Crystal structure of 5-bromo-1-ethylindoline-2,3-dione

Abstract

The title compound, C10H8BrNO2, crystallizes with two independent molcules (A and B) in the asymmetric unit. In each molecule, the indoline ring system is almost planar, with the largest deviation from the mean plane being 0.016 (2) Å in molecule A and 0.040 (13) Å in molecule B. In each molecule, the ethyl group is nearly perpendicular to the indoline ring system with C—C—N—C torsion angles of −94.8 (3) and 93.0 (3)° in molecules A and B, respectively. In the crystal, the two molecules are inclined to each other, making a dihedral angle of 6.28 (8)°. In the molecular packing, the A and B molecules are linked by C—H...O hydrogen bonds, forming –A–B–A–B– chains along [01-1]. Parallel chains are linked via a weak slipped parallel π–π interaction [inter-centroid distance = 3.6107 (14) Å] and a short Br...O contact [3.183 (2) Å], forming a three-dimensional structure.

Keywords

• crystal structure
• indoline
• C—H...O hydrogen bonds
• slipped parallel π–π interaction
• short Br...O interaction