1-[2-(3-Methoxyphenyl)ethyl]pyrrolidine-2,5-dione

In the title compound, C13H15NO3, the pyrrolidine ring makes a dihedral angle of 4.69 (9)° with the 3-methoxy-phenyl ring. In the crystal, hydrogen-bonded chains running along [101] are generated by connecting neighbouring molecules via C—H⋯O hydrogen bonds. Parallel chains are linked by further C—H⋯O hydrogen bonds, forming a three-dimensional structure.

In the title compound, C 13 H 15 NO 3 , the pyrrolidine ring makes a dihedral angle of 4.69 (9) with the 3-methoxy-phenyl ring. In the crystal, hydrogen-bonded chains running along [101] are generated by connecting neighbouring molecules via C-HÁ Á ÁO hydrogen bonds. Parallel chains are linked by further C-HÁ Á ÁO hydrogen bonds, forming a three-dimensional structure.

Comment
Pyrrolidine-2,5-dione derivates are an important class of heterocylic compounds with essential applications in medicinal chemistry and organic synthesis. They exhibit numerous bioactivities, for example anticonvulsant (Obniska et al., 2012;Kaminski et al., 2011) and tyrosinase inhibitory activity (Ha et al., 2011). In the field of organic chemistry derivates, like 1-bromopyrrolidine-2,5-dione (NBS), are the most commonly used halogenation reagents. In view of the different applications of this class of compounds, we have synthesized the title derivative and report herein on its crystal structure.
In the crystal, hydrogen-bonded chains running along [101] are generated by connecting neighbouring molecules via C -H···O hydrogen bonds (Table 1 and Fig. 2). Parallel chains are linked by further C-H···O hydrogen bonds forming a three-dimensional structure (Table 1 and Fig. 2).

Experimental
3-methoxy phenethylamine (1.51 g, 10 mmol) and succinic anhydride (1.2 g, 12 mmol) were stirred at room temperature in dry ethyl acetate for 30 min. Ethyl acetate was removed under reduced pressure, and the resulting residue was dissolved in toluene. Acetyl chloride (5 equiv) was then added and the mixture refluxed for 1 h. The reaction mixture was washed with aqueous Na 2 CO 3 and dried over anhydrous Na 2 SO 4 , filtered and concentrated under reduced pressure followed by silica gel column purification using hexane ethyl acetate (30:70) as eluent to afford the title compound as a colourless solid. Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a solution of the title compound in ethanol at room temperature.

Refinement
The H atoms were placed in calculated positions and treated as riding atoms: C-H = 0.93 Å to 0.97 Å, with U iso (H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.

Figure 2
The crystal packing of the title compound viewed along the c axis. Hydrogen bonds are shown as dashed lines (see Table   1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).  (15) Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. 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.