Tert-Butyl 6-bromo-1,4-dimethyl-9H-carbazole-9-carboxylate

Abstract

The title compound, C19H20BrNO2, consists of a carbazole skeleton with methyl groups at positions 1 and 4, a protecting group located at the N atom and a Br atom at position 6. The pyrrole ring is oriented at dihedral angles of 1.27 (7) and 4.86 (7)° with respect to the adjacent benzene rings. The dihedral angle between the benzene rings is 5.11 (7). The crystal structure is determined mainly by intra­molecular C—H⋯O and inter­molecular π–π inter­actions. π-stacking between adjacent molecules forms columns with a parallel arrangement of the carbazole ring systems. The presence of the tert-but­oxy­carbonyl group on the carbazole N atom and the intra­molecular hydrogen bond induce a particular conformation of the exocyclic N—C bond within the mol­ecule.