2-Benzyl-5-methoxyisoindoline-1,3-dione

The title N-benzylphthalimide derivative, C16H13NO3, consists of two planar moieties, viz. the phthalimide system (r.m.s. deviation = 0.007 Å) and the phenyl ring, which make a dihedral angle of 84.7 (6)°. The methoxy group is almost coplanar with the phathalimide ring, as shown by the C—C—O—C torsion angle of −171.5 (2)°. In the crystal, the molecules are self-assembled via non-classical C—H⋯O hydrogen bonds, forming a tape motif along [110].


Comment
Phthalimide derivatives represent a significant family of organic compounds because of their numerous applications in different fields of chemistry. They are not only useful intermediates for synthesis (Luzzio, 2005), but are also important The title compound (I) is a N-benzylphthalimide substituted at C5 with a methoxy group. It was obtained by the reaction of dimethyl phthalimide with benzyl hydrazine under microwave irradiation.
The molecular structure of (I) is illustrated in Figure 1. There are some similar structures reported before (Warzecha et al., 2006a;Warzecha et al., 2006b;Warzecha et al., 2006c;Jiang et al., 2008). The molecule consists of two planar moieties, the phthalimide system and the phenyl ring, linked by the methylene group C9 (N2-C9-C10 bond angle of 114.4°), resulting in a non-planar structure. The two planar subunits make a dihedral angle of 84.7 (6)°, which is similar to the value reported for the same angle in the crystal structure of the monoclinic form of the parent N-benzylphthalimide (Jiang et al., 2008). Furthermore, the methoxy group at C5 is almost coplanar with the phathalimide ring [torsion angle In addition, the C1-N2-C9-C10 and C3-N2-C9-C10 torsion angles of 93.1 (3)° and -86.0 (3)°, respectively, are also very similar to those of N-benzylphthalimide (Jiang et al., 2008) and they corroborate that the phenyl group is virtually orthogonal to the phthalimide benzene ring. In the crystal structure, the molecules are self-assembled via nonclassical C-H···O hydrogen bonds, involving CH and CH 3 groups as donors and oxygen atoms as acceptors, to form a one-dimensional supramolecular organization (Table 1, Figure 2).

Figure 1
Molecular structure of (I) showing the atom-numbering scheme. Displacement ellipsoids are shown at the 50% probability level.

Figure 2
View of the supramolecular tape motif in the crystal structure of the title compound. View of the unit-cell contents of (I).

2-Benzyl-5-methoxyisoindoline-1,3-dione
Crystal data Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq C1 0.3240 (