N-(2-Chlorophenyl)-2-nitrobenzenesulfonamide

U Chaithanya,Sabine Foro,B Thimme Gowda

doi:10.1107/s1600536812033107

U Chaithanya, Sabine Foro + Show 1 more

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https://doi.org/10.1107/s1600536812033107

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Abstract

In the title compound, C12H9ClN2O4S, the N—H bond in the –SO2—NH– segment is syn to both the ortho-nitro group in the sulfonylbenzene ring and the ortho-Cl atom in the aniline ring. The molecule is twisted at the S—N bond with a torsion angle of 75.0 (2)°. The dihedral angle between the sulfonylbenzene and aniline rings is 54.97 (11)°. The amide H atom shows bifurcated hydrogen bonding, generating S(7) and C(4) motifs. In the crystal, N—H⋯O(S) hydrogen bonds link the molecules into chains.

Highlights

In the title compound, C12H9ClN2O4S, the N—H bond in the – SO2—NH– segment is syn to both the ortho-nitro group in the sulfonylbenzene ring and the ortho-Cl atom in the aniline ring
H atoms treated by a mixture of independent and constrained refinement max = 0.23 e Å3
The molecule is twisted at the S—N bond with a torsion angle of 75.0 (2)

Summary

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H atoms treated by a mixture of independent and constrained refinement max = 0.23 e Å3. R factor = 0.043; wR factor = 0.098; data-to-parameter ratio = 15.5. C12H9ClN2O4S, the N—H bond in the – SO2—NH– segment is syn to both the ortho-nitro group in the sulfonylbenzene ring and the ortho-Cl atom in the aniline ring. The molecule is twisted at the S—N bond with a torsion angle of 75.0 (2). The dihedral angle between the sulfonylbenzene and aniline rings is 54.97 (11). The amide H atom shows bifurcated hydrogen bonding, generating S(7) and C(4) motifs. N—H O(S) hydrogen bonds link the molecules into chains

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