Research Article: N-(2-Formyl­phen­yl)-4-toluene­sulfonamide: a second monoclinic polymorph

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): S. Murugavel, N. Manikandan, D. Kannan, M. Bakthadoss.


The title compound, C14H13NO3S, (I), is a second monoclinic polymorph. The original polymorph, (II), was reported by Mahía et al. [Acta Cryst. (1999), C55, 2158–2160]. Polymorph (II) crystalllized in the space group P21/c (Z = 4), whereas the title polymorph (I) occurs in the space group P21/n (Z = 4). The dihedral angle between the two aromatic rings is 75.9 (1)° in (I) compared to 81.9 (1)° for (II). In both polymorphs, two S(6) rings are generated by intra­molecular N—H⋯O and C—H⋯O hydrogen bonds, resulting in similar mol­ecular geometries. However, the two polymorphs differ concerning their crystal packing. In (I), mol­ecules are linked into C(8) zigzag chains along the b axis by C—H⋯O hydrogen bonds, whereas in (II) mol­ecules are linked by C—H⋯O hydrogen bonds, forming C(7) chains along the b axis. The title polymorph is further stabilized by inter­molecular C—H⋯π and π–π inter­actions [centroid–centroid distance = 3.814 (1) Å]. These inter­actions are not evident in polymorph (II).

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For biological applications of sulfonamides, see: Connor (1998 ▶); Berredjem et al. (2000 ▶); Lee & Lee (2002 ▶); Xiao & Timberlake (2000 ▶). For the first monoclinic polymorph, see: Mahía et al. (1999 ▶). For a related structure, see: Zhang et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).