2-(4-Sulfamoylphenyl)hydrazin-1-ium chloride

The hydrazinium residue in the cation of the title salt, C6H10N3O2S+·Cl−, is twisted out of the plane of the benzene ring to which it is attached [N—N—C—C torsion angle = 25.9 (2)°] and the amino group is almost perpendicular to the benzene ring [N—S—C—C torsion angle = 88.71 (16)°]. In the crystal, the cations are linked by N—H⋯O hydrogen bonds and π–π interactions [ring centroid distance = 3.7280 (11) Å], forming layers in the bc plane that are connected by N—H⋯Cl hydrogen bonds.

The hydrazinium residue in the cation of the title salt, C 6 H 10 N 3 O 2 S + ÁCl À , is twisted out of the plane of the benzene ring to which it is attached [N-N-C-C torsion angle = 25.9 (2) ] and the amino group is almost perpendicular to the benzene ring [N-S-C-C torsion angle = 88. 71 (16) ]. In the crystal, the cations are linked by N-HÁ Á ÁO hydrogen bonds andinteractions [ring centroid distance = 3.7280 (11) Å ], forming layers in the bc plane that are connected by N-HÁ Á ÁCl hydrogen bonds.
The crystallographic asymmetric unit of (I) comprises a hydrazinium cation charge balanced by a chloride, Fig. 1. The hydrazinium residue is twisted out of the plane of the benzene ring to which it is attached as seen in the value of the N1-N2-C4-C3 torsion angle of 25.9 (2)°. The amino group occupies a position perpendicular to the benzene ring with the N3-S1-C1-C2 torsion angle being 88.71 (16)°; the ammonium and amino groups are orientated to opposite sides of the benzene ring.
The cations are linked by N-H···O hydrogen bonds, Table 1, and π-π interactions [ring centroid distance = 3.7280 (11) Å for symmetry operation: 1 -x, 1 -y, 1 -z] to form layers in the bc plane. The cations are connected to the chloride anions by N-H···Cl hydrogen bonds, Table 1, leading to a three-dimensional architecture.

Experimental
Diazotization of sulfonamide with NaNO 2 /HCl followed by reduction with sodium sulfite afforded the title salt which was crystallized from ethanol as irregular light-brown chunks. Yield: 72%. M.pt. 488-490 K.

Refinement
Carbon-bound H-atoms were placed in calculated positions [C-H = 0.95 Å, U iso (H) = 1.2U eq (C)] and were included in the refinement in the riding model approximation. The N-H atoms were located in a difference Fourier map, and were refined with a distance restraint of N-H = 0.88±0.01 Å; their U iso values were refined.