N-[4-(Benzylsulfamoyl)phenyl]acetamide

A folded conformation is found for the title compound, C15H16N2O3S, whereby the benzene rings come into close proximity [centroid–centroid distance = 4.0357 (12) Å and the dihedral angle between them = 24.37 (10)°]. The amide group is coplanar with the benzene ring to which it is bound [C—C—N—C torsion angle = 11.1 (3)°]. In the crystal packing, two-dimensional arrays in the (101) plane are formed via N—H⋯O hydrogen bonding.

We are grateful to Mr Munawar Hussain, Engineering Cell GC University, Lahore, for providing support services to the Materials Chemistry Laboratory.
The molecule of C 15 H 16 N 2 O 3 S has a folded conformation with the benzene ring of the benzyl group somewhat orientated over the S-bound benzene ring. The rings are approximately parallel, forming a dihedral angle of 24.37 (10) °; the distance between the ring centroids is 4.0357 (12) Å. The amide group is essentially co-planar with the ring to which it is bound as seen in the C10-C11-N2-C14 torsion angle of 11.1 (3) °.
The crystal packing is dominated by N-H···O hydrogen bonds whereby the N1-H atom forms a hydrogen bond to the amide-carbonyl, and the amide N2-H forms a contact with the S-bound O2 atom, Table 1. The former leads to centrosymmetric aggregates and these are connected by the latter into a 2-D array in the (1 0 1) plane, Fig. 2.

Experimental
To 4-acetamidobenzenesulfonyl chloride (498 mg, 2.14 mmol) in distilled water (10 ml) was added benzylamine (234 ml, 2.14 mmol), the reaction mixture was stirred at room temperature while maintaining the pH of the reaction mixture at 8 using 3% sodium carbonate. The progress of the reaction was monitored by TLC. After consumption of all the reactants, the precipitates were filtered, dried and crystallized from methanol to yield colourless crystals.
The N-bound H atom was refined with the distance restraint N-H = 0.88±0.01 Å, and with U iso (H) = 1.2U eq (N). Fig. 1 as those based on F, and R-factors based on ALL data will be even larger.