Crystal structure of 5-bromo-1-ethyl-indoline-2,3-dione

Acta Crystallogr E Crystallogr Commun. 2015 Dec 6;71(Pt 12):o1024-5. doi: 10.1107/S2056989015023002. eCollection 2015 Dec 1.

Abstract

The title compound, C10H8BrNO2, crystallizes with two independent molcules (A and B) in the asymmetric unit. In each mol-ecule, the indoline ring system is almost planar, with the largest deviation from the mean plane being 0.016 (2) Å in mol-ecule A and 0.040 (13) Å in mol-ecule B. In each mol-ecule, 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 mol-ecules A and B, respectively. In the crystal, the two mol-ecules are inclined to each other, making a dihedral angle of 6.28 (8)°. In the molecular packing, the A and B mol-ecules 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 inter-action [inter-centroid distance = 3.6107 (14) Å] and a short Br⋯O contact [3.183 (2) Å], forming a three-dimensional structure.

Keywords: C—H⋯O hydrogen bonds; crystal structure; indoline; short Br⋯O inter­action; slipped parallel π–π inter­action.