organic compounds 1490 # 2000 International Union of Crystallography Printed in Great Britain – all rights reserved Acta Cryst. (2000). C56, 1490–1491 4-Methyl-N-[2-(p-tolylsulfanyl)- phenyl]benzenesulfonamide Surajit Banerjee, a Alok K. Mukherjee, a * Bidisha Nandi, b Nitya G. Kundu b and Madeleine Helliwell c a Department of Physics, Jadavpur University, Calcutta 700 032, India, b Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta 700 032, India, and c Department of Chemistry, University of Manchester, Manchester M13 9PL, England Correspondence e-mail: akm@juphys.ernet.in Received 25 July 2000 Accepted 14 September 2000 The title compound, C 20 H 19 NO 2 S 2 , is formed by a palladium– copper-catalyzed reaction between 4-methyl-N-[2-(prop-2- ynylsulfanyl)phenyl]benzenesulfonamide and p-iodotoluene. The molecules contain three essentially planar parts, namely an aminothiophenol moiety (A), a toluenesulfone moiety excluding the oxo ligands (B) and a tolyl group (C), approximately orthogonal to each other; the dihedral angles A/B, A/C and B/C are 111.6 (1), 89.3 (1) and 101.4 (1) , respectively. Intermolecular N—HO hydrogen bonds link the molecules into infinite one-dimensional chains. Comment Metal-catalyzed heteroannulation is an important synthetic tool for the formation of a variety of heterocyclic systems of biological importance (Mukherjee et al., 2000; Kundu et al., 1999). During the synthesis of a sulfur-containing heterocyclic compound, benzothiazine, (II), via a palladium–copper-cata- lyzed reaction between 4-methyl-N-[2-(prop-2-ynylsulfanyl)- phenyl]benzenesulfonamide, (I), and p-iodotoluene, the title compound, 4-methyl-N-[2-(p-tolylsulfanyl)phenyl]benzene- sulfonamide, (III), was obtained through a novel depropargylation and S-arylation. The X-ray structural study of (III) was undertaken in order to establish the regio- and stereospecificities of the reaction. The structure of (III) (Fig. 1) consists of three essentially planar parts (A, B and C) approximately orthogonal to each other. The central aminothiophenol moiety A (atoms C8–C13, N1, S2) is planar to within 0.031 (4) A ˚ . The other two parts, p-toluenesulfone excluding the two oxo ligands (B: atoms C1– C7, S1) and p-tolyl (C: atoms C14–C20), with a maximum deviation of 0.025 (4) A ˚ for an in-plane atom (C1) from the corresponding least-squares plane, are inclined by 101.4 (1) with respect to each other. The dihedral angles A/B and A/C are 111.6 (1) and 89.3 (1) , respectively. The torsion angle C5—S1—N1—C8 of 62.4 (3) establishes a gauche confor- mation of the molecule when viewed along the S—N axis. The geometric parameters of (III) agree well with those found in other substituted p-toluenesulfonamide structures (Parvez et al., 1999; Goswami et al., 1998; Bachechi et al., 1996; Gainsford & Lensink, 1996). The N atom with a bond angle sum of 349.5 (2) indicates a pyramidal configuration. The angular disposition of the bonds about the sulfonyl S atom (S1) deviate significantly from that of regular tetrahedron. The widening of the O1—S1—O2 angle of 119.1 (1) from the ideal tetrahedral value is presumably the result of the repulsive interaction between the short S O bonds (Table 1). The lack of bonding in the branches among the phenyl rings precludes any possible conjugation across the whole mol- ecule. The aromatic nature of the rings is therefore localized within the rings and on their direct substituents. One of the sulfonyl O atoms, O1, is nearly coplanar with the tolyl substituent [O1—S1—C5—C6 14.2 (3) ]; the other sulfonyl O atom, O2, forms a torsion angle O2—S1—C5—C6 of 144.8 (3) . In the solid state, the molecules translated in the b direction are linked through N1—H8O2 intermolecular hydrogen bonds (Table 2) to form infinite one-dimensional chains. Acta Crystallographica Section C Crystal Structure Communications ISSN 0108-2701 Figure 1 ZORTEP (Zsolnai, 1995) view (50% probability level) of the title molecule.