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4-Chloro-N-(3-methyl-phen-yl)benzene-sulfonamide.

ABSTRACT: In the crystal of the title compound, C(13)H(12)ClNO(2)S, the N-H bond is anti to the meta-methyl group in the aniline ring. The C-SO(2)-NH-C torsion angle is -57.6?(2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 84.7?(1)°. The crystal structure features inversion-related dimers linked by pairs of N-H?O hydrogen bonds.

SUBMITTER: Shakuntala K

PROVIDER: S-EPMC3120465 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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4-Chloro-N-(3-methyl-phen-yl)benzene-sulfonamide.

Shakuntala K K Foro Sabine S Gowda B Thimme BT

Acta crystallographica. Section E, Structure reports online 20110528 Pt 6

In the crystal of the title compound, C(13)H(12)ClNO(2)S, the N-H bond is anti to the meta-methyl group in the aniline ring. The C-SO(2)-NH-C torsion angle is -57.6 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 84.7 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds. ...[more]

PMID: 21754899

Similar Datasets

Crystal structures of isomeric 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)benzene-sulfonamide, 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide.

Project description:The crystal structures of three isomeric compounds of formula C14H13Cl2NO2S, namely 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)-benzene-sulfonamide (I), 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide (II) and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide (III) are described. The mol-ecules of all the three compounds are U-shaped with the two aromatic rings inclined at 41.3 (6)° in (I), 42.1 (2)° in (II) and 54.4 (3)° in (III). The mol-ecular conformation of (II) is stabilized by intra-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions. The crystal structure of (I) features N-H⋯O hydrogen-bonded R22(8) loops inter-connected via C(7) chains of C-H⋯O inter-actions, forming a three-dimensional architecture. The structure also features π-π inter-actions [Cg⋯Cg = 3.6970 (14) Å]. In (II), N-H⋯O hydrogen-bonded R22(8) loops are inter-connected via π-π inter-actions [inter-centroid distance = 3.606 (3) Å] to form a one-dimensional architecture running parallel to the a axis. In (III), adjacent C(4) chains of N-H⋯O hydrogen-bonded mol-ecules running parallel to [010] are connected via C-H⋯π inter-actions, forming sheets parallel to the ab plane. Neighbouring sheets are linked via offset π-π inter-actions [inter-centroid distance = 3.8303 (16) Å] to form a three-dimensional architecture.

| S-EPMC5418781 | biostudies-literature

4-Chloro-N-(3-chloro-phen-yl)-2-methyl-benzene-sulfonamide.

Project description:In the title compound, C(13)H(11)Cl(2)NO(2)S, the conformation of the N-H bond in the C-SO(2)-NH-C segment is anti to the meta-Cl atom on the aniline ring and syn to the ortho-methyl group on the sulfonyl-benzene ring. Furthermore, the torsion angle of the C-SO(2)-NH-C segment in the mol-ecule is 80.1?(3)°. The two benzene rings are tilted relative to each other by 70.9?(1)°. In the crystal, pairs of inter-molecular N-H?O hydrogen bonds link the mol-ecules via inversion-related dimers into infinite column-like chains.

| S-EPMC3006774 | biostudies-literature

4-Chloro-N-(2-chloro-phen-yl)-2-methyl-benzene-sulfonamide.

Project description:In the crystal structure of the title compound, C(13)H(11)Cl(2)NO(2)S, the conformations of the N-C bond in the C-SO(2)-NH-C segment are trans and gauche with respect to the S=O bonds. The C-S(O(2))-N(H)-C torsion angle is 74.8 (4)°, indicating that the mol-ecule is bent at the S atom. In the crystal structure, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur. An intramolecular N-H⋯Cl inter-action is also present.

| S-EPMC2968972 | biostudies-literature

4-Chloro-2-methyl-N-(3-methyl-phen-yl)benzene-sulfonamide.

Project description:The N-H bond in the title compound, C(14)H(14)ClNO(2)S, the dihedral angle between the two benzene rings is 75.5?(1)°. The crystal structure features inversion-related dimers linked by pairs of N-H?O hydrogen bonds.

| S-EPMC2980238 | biostudies-literature

4-Chloro-2-methyl-N-(4-methyl-phen-yl)benzene-sulfonamide.

Project description:The asymmetric unit of the title compound, C(14)H(14)ClNO(2)S, contains two independent mol-ecules. The torsion angles of the C-SO(2)-NH-C segments in the two mol-ecules are -76.5 (5) and -48.3 (4)°. The two aromatic rings are tilted relative to each other by 76.6 (2)° in one mol-ecule and 70.7 (2)° in the other. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

| S-EPMC3007926 | biostudies-literature

4-Chloro-2-methyl-N-(2-methyl-phen-yl)-benzene-sulfonamide.

Project description:In the crystal structure of the title compound, C(14)H(14)ClNO(2)S, the two aromatic rings are tilted relative to each other by 45.8 (1)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur.

| S-EPMC2969047 | biostudies-literature

4-Chloro-N-(2,4-dimethyl-phen-yl)-2-methyl-benzene-sulfonamide.

Project description:In the title compound, C(15)H(16)ClNO(2)S, the C-SO(2)-NH-C torsion angle is 67.45?(17)°. The two aromatic rings are tilted relative to each other by 44.5?(1)°. The crystal structure features inversion-related dimers linked by pairs of N-H?O hydrogen bonds..

| S-EPMC3201300 | biostudies-literature

4-Chloro-N-(2,5-dimethyl-phen-yl)-2-methyl-benzene-sulfonamide.

Project description:The asymmetric unit of the title compound, C(15)H(16)ClNO(2)S, contains three independent moleules. The conformation of the N-H bonds are anti to the ortho-methyl groups of the sulfonyl benzene rings in all the mol-ecules. The sulfonyl and the aniline benzene rings are tilted relative to each other by 43.0?(2), 37.0?(2) and by 46.0?(1)° in the three mol-ecules. In the crystal, inter-molecular N-H?O hydrogen bonds link each of the mol-ecules into centrosymmetric dimers.

| S-EPMC3247308 | biostudies-literature

4-Chloro-N-(2,6-dimethyl-phen-yl)-2-methyl-benzene-sulfonamide.

Project description:In the title compound, C(15)H(16)ClNO(2)S, the C-SO(2)-NH-C torsion angle is -61.15?(16)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 38.8?(1)°. The crystal structure features inversion-related dimers linked by pairs of N-H?O hydrogen bonds.

| S-EPMC3247307 | biostudies-literature

4-Chloro-N-(3,4-dichloro-phen-yl)-2-methyl-benzene-sulfonamide.

Project description:In the title compound, C(13)H(10)Cl(3)NO(2)S, the N-C bond in the C-SO(2)-NH-C segment forms trans and gauche torsion angles with respect to the S=O bonds. Further, the N-H bond in the C-SO(2)-NH-C segment is anti to the meta-Cl atom in the anilino benzene ring and nearly syn with respect to the ortho-methyl group in the sulfonyl benzene ring. The C-SO(2)-NH-C torsion angle is -49.4?(2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 54.6?(1)°. In the crystal, mol-ecules are linked into chains along the c-axis direction by inter-molecular N-H?O hydrogen bonds.

| S-EPMC3247351 | biostudies-literature

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