Date Published: August 01, 2012
Publisher: International Union of Crystallography
Author(s): Hiroki Takahashi.
The title compound [systematic name: 2-(4-methoxybenzyl)isoindoline-1,3-dione], C16H13NO3, represents a triclinic polymorph of the previously reported monoclinic form [Warzecha et al. (2006 ▶). Acta Cryst. E62, o5450–o5452]. The reaction of potassium phthalimide and 4-methoxybenzyl chloride in dimethylformamide gave platelet-shaped crystals; these were harvested and then needle-shaped crystals were deposited. The platelet- and needle-shaped crystals correspond to the triclinic and monoclinic forms, respectively. The N—C—Car—Car torsion angles between the ring systems are −82.66 (14) and 95.28 (13)°, resulting in a roof-shaped conformation. In the crystal, molecules are accumulated by offset face–face π–π interactions between phthalimide units [centroid–centroid distances = 3.640 (2) and 3.651 (2) Å], with interplanar distances of 3.321 (1) and 3.435 (1) Å. Weak intermolecular Caryl—H⋯O=C and Calkyl—H⋯O=C contacts form C(8) and C(11) infinite chain motifs, respectively.
For the crystal structure of the monoclinic form of the title compound, see: Warzecha et al. (2006b ▶). For a photochemical study of the title compound, see: Warzecha, Görner et al. (2006 ▶). For related compounds, see: Lü et al. (2006 ▶); Warzecha et al. (2006a ▶); Chen et al. (2006 ▶). For graph-set motifs, see: Etter (1990 ▶).