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The title structure, (3 R *, 1′ S *, 3′ R *)-3-(1′- tert- butylamino-1′ H ,3′ H -benzo[ c ]furan-3′-yl)-2- tert -butyl-2,3-dihydro-1 H- benzo[ c ]pyrrol-1-one has been determined at 290 and 150 K by single-crystal X-ray diffraction. The structure comprises two symmetry independent molecules with very similar conformations which differ mostly by orientations of the  tert -butyl groups, situated at the periphery of these molecules. The molecules are composed of two parts, the cores of which are isoindolinone and isobenzofuran rings being bound by C–C bonds. The planarities of the pyrrolone and furan rings are compared with the known structures retrieved from the Cambridge Crystal Structure Database. It transpires in the title molecules, the planarity of the carbonyl-substituted pyrrole rings is exceptionally distorted in contrast to the furan rings. This fact is just the opposite of the tendency inferred from the Cambridge Crystal Structure Database. The reason may be the influence of the voluminous  tert -butyl group which is attached to the nitrogen of the pyrrole group, as well as short centroid–centroid distances between the carbonyl-substituted pyrrole and furan rings. Cohesion forces between the molecules and their parts are provided by weak interactions only: The packing suggests C–H···O,  π – π -electron ring interactions, N–H··· π -electron ring as well as C–H··· π -electron ring interactions. The structure determination of the title compound, the product of the reaction of  o -phthalaldehyde with  tert -butylamine, has provided indication about the mechanism of a chemical reaction which resulted in the formation of the title molecule.

zeitschrift für kristallographie - crystalline materials

Planarity of substituted pyrrole and furan rings in (3 R *, 1′ S *, 3′ R *)-3-(1′- tert- butylamino-1′ H , 3′  H -benzo[ c ]furan-3′-yl)-2- tert -butyl-2,3-dihydro-1 H- benzo[ c ]pyrrol-1-one