4-[(1,3-Dioxoisoindolin-2-yl)methyl]benzenesulfonamide

The title compound, C15H12N2O4S, is V-shaped with the isoindoline ring system (r.m.s. deviation = 0.006 Å) inclined to the benzene ring by 84.27 (13)°. In the crystal, inversion dimers are formed via pairwise N—H⋯O hydrogen bonds. These dimers associate further into corrugated ribbons, via pairwise N—H⋯O and C—H⋯O hydrogen bonds, propagating along the a-axis direction and lying parallel to (001).

As part of our ongoing studies in drug design and discovery, we report herein on the crystal structure of the title compound.

Experimental
The synthesis of the title compound has been reported previously (Abdel-Aziz et al., 2011a). A solution of 4-(aminomethyl)benzene-1-sulfonamide (10 mmol) and phthalic anhydride (10 mmol) in glacial acetic acid (10 ml) was heated under reflux for 6 h. After evaporation of the reaction mixture to dryness under reduced pressure, the residue was neutralized using aqueous sodium bicarbonate solution (4%) until effervescence ceased. The precipitate obtained was washed with water, dried in vacuo and recrystallized from methanol yielding colourless plate-like crystals.

Refinement
The NH 2 H atoms were located in a difference electron-density map and freely refined. The C bound H atoms were included in calculated positions and treated as riding atoms: C-H = 0.95 and 0.99 Å for CH and CH 2 H atoms, respectively, with U iso (H) = 1.2U eq (C).  A view of the molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
A view along a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (N-H···O purple; C-H···O green; see Table 1 for details).

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. H-atoms attached to carbon were placed in calculated positions (C-H = 0.95 Å) and included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq S1 0.34446 (