<i>N</i>-(4-Aminophenyl)-4-methylbenzenesulfonamide

The title compound, C10H14N2O3S, crystallized with two molecules (A and B) in the asymmetric unit. The terminal methyl group of the ethylsulfonamide moiety in molecule B is disordered over two sets of sites with an occupancy ratio of 0.61 (1):0.39 (1). Both molecules have L-shaped conformations. In molecule A, the dihedral angles between the benzene ring and its ethylsulfonamide and methylamide substituents are 83.5 (3) and 13.34 (18)°, respectively. Equivalent values for molecule B are 87.9 (3) and 6.32 (16)°, respectively. The C—S—N—C torsion angles are 66.5 (3)° for A and −64.4 (3)° for B, indicating similar twists about the S—N bonds, but in opposite senses. In the crystal, the A molecules are linked by pairs of Ns—H⋯O (s = sulfonamide) hydrogen bonds, generating inversion dimers containing R 2 2(8) rings, while the B molecules are linked by Ns—H⋯O hydrogen bonds into C(10) [100] chains. Finally, Na—H⋯O (a = amide) hydrogen bonds link the A-molecule dimers and B-molecule chains into a three-dimensional network.

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“…For related structures, see: Hou et al (2009); Khan et al (2011); Rehman et al (2011). Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

N-[4-(Ethylsulfamoyl)phenyl]acetamide

et al. 2011

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Crystal structure of 4-methyl-N-propylbenzenesulfonamide

Stenfors¹,

Collins²,

Duran³

et al. 2020

Acta Cryst E

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The crystal structure of the title sulfonamide, C10H15NO2S, comprises two molecules in the asymmetric unit. The S=O bond lengths of the sulfonamide functional group range from 1.428 (2) to 1.441 (2) Å, with S—C bond lengths of 1.766 (3) Å (for both molecules in the asymmetric unit), and S—N bond lengths of 1.618 (2) and 1.622 (3) Å, respectively. When both molecules are viewed down the N—S bond, the propyl group is gauche to the toluene moiety. In the crystal structure, molecules of the title compound are arranged in an intricate three-dimensional network that is formed via intermolecular C—H...O and N—H...O hydrogen bonds. The crystal structure was refined from a crystal twinned by inversion.

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N-(4-Aminophenyl)-4-methylbenzenesulfonamide

Cited by 2 publications

References 7 publications

N-[4-(Ethylsulfamoyl)phenyl]acetamide

N-[4-(Ethylsulfamoyl)phenyl]acetamide

Crystal structure of 4-methyl-N-propylbenzenesulfonamide

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