4-Methyl-N-(4-methylphenylsulfonyl)-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]benzenesulfonamide

There are two independent molecules in the asymmetric unit of the title compound, C24H22N2O4S3. In each, the sulfonamide N atoms reveal nearly a trigonal-planar geometry with two S atoms of the O=S=O groups and one C atom of the thiazole ring; the angles around the N atoms are between 117.00 (13) and 123.86 (9)°. The methylphenylsulfonyl groups are in anti conformations, forming dihedral angles of 78.00 (7)/72.53 (5) and 77.09 (6)/71.50 (7)° with the trigonal S—N—S planes in the two molecules. The thiazole groups are rotated around the C—N bonds and are almost perpendicular to the S—N—S plane [dihedral angles of 78.00 (7)/72.53 (5) and 77.09 (6)/71.50 (7)°]. In the crystal, pairs of C—H⋯O interactions, with the O atoms of the sulfonamide groups as acceptors, link each of the independent molecules into inversion dimers.

There are two independent molecules in the asymmetric unit of the title compound, C 24 H 22 N 2 O 4 S 3 . In each, the sulfonamide N atoms reveal nearly a trigonal-planar geometry with two S atoms of the O S O groups and one C atom of the thiazole ring; the angles around the N atoms are between 117.00 (13) and 123.86 (9) . The methylphenylsulfonyl groups are in anti conformations, forming dihedral angles of 78.00 (7)/ 72.53 (5) and 77.09 (6)/71.50 (7) with the trigonal S-N-S planes in the two molecules. The thiazole groups are rotated around the C-N bonds and are almost perpendicular to the S-N-S plane [dihedral angles of 78.00 (7)/72.53 (5) and 77.09 (6)/71.50 (7) ]. In the crystal, pairs of C-HÁ Á ÁO interactions, with the O atoms of the sulfonamide groups as acceptors, link each of the independent molecules into inversion dimers. 2 restraints H-atom parameters constrained Á max = 0.23 e Å À3 Á min = À0.28 e Å À3 Table 1 Hydrogen-bond geometry (Å , ). Symmetry codes: (i) Àx þ 1; Ày þ 2; Àz þ 1; (ii) Àx þ 1; Ày þ 2; Àz.
The title compound I crystallized with two independent molecules (A and B) in the asymmetric unit (Fig. 1). The geometries around the N13 and N42 atoms are almost trigonal planar with bonding angles ranging from 117.00° to 123.86°. The sulfonamide nitrogen atoms are bonded to a carbon atom of the thiazole ring and two sulfur atoms of the O=S=O groups, the distances of the C-N bonds are of 1.426 (2) Å for both molecules, and the N-S bonds are between 1.6902 (16) and 1.7040 (17) Å. The thiazole rings are rotated around C-N bond foming the dihedral angles of 85.57 (5)° and 89.28 (5)° with the planes O2S-N-SO2, in molecule A and B, respectively. The methylphenylsulfonyl groups keep anti-conformations forming a dihedral angles of 78.00 (7)°, 72.53 (5)° and 77.09 (6)°, 71.50 (7)° with the trigonal plane S -N-S, in the molecules A and B, respectively. The sulfur atoms of the sulfonamide groups are in a distorted tetrahedral geometry with angles varying from 103.43 (8) to 121.39 (1)°, and S=O bonds from 1.4175 (15) to 1.42358 (14) Å. The thiazole and p-tolyl groups in the molecule B exhibit a coplanar arrangement, while in the molecule A these moieties form an angle of 17.20 (7)° between these planes. Each independent molecule form a dimer arrangement by C-H···O interactions (Table 1, Fig. 2). The crystal packing in the title compound is stabilized by the C-H···O=S intermolecular interactions.
The organic layers were dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was crystallized from acetone to yield single crystals of the title compound (314 mg, 0.63 mmol, 60%).

Refinement
H atoms were included in calculated position (C-H = 0.93 Å for aromatic H, and C-H = 0.96 Å for methyl H), and refined using a riding model U iso (H) = 1.2 U eq of the carrier atoms. In the refinement 10 reflections were considered as disagreeable and were omitted.

Figure 1
The asymmetric unit of the title compound (I). All non-hydrogen atoms are shown as ellipsoids with probability level of 40%. Hydrogen atoms are omitted.

Figure 2
Hydrogen bonds in the crystal packing of the title compound, shown by dashed lines.