Sulfonyl Benzene Rings Research Articles

2,4-Dichloro-N-(2,6-dimethylphenyl)benzenesulfonamide

In the crystal of the title compound, C14H13Cl2NO2S, the N—H bond in the C—SO2—NH—C segment orients itself away from the two ortho-methyl groups in the aniline benzene ring and towards the ortho-chloro group of the sulfonyl benzene ring. The mol­ecule is bent at the S atom with a C—SO2—NH—C torsion angle of −100.48 (18)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 69.6 (1)°. Inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into infinite chains.

4-Chloro-N-(2,3-dimethylphenyl)-2-methylbenzenesulfonamide

The asymmetric unit of the title compound, C15H16ClNO2S, contains two independent moleules. The conformation of the N—H bonds are anti to the ortho-methyl groups in the sulfonyl benzene rings of both the mol­ecules, while the N—H bonds are anti to the ortho- and meta-methyl groups in the aniline ring of one of the mol­ecules and syn in the other. Furthermore, the torsion angles of the C—SO2—NH—C segments in the two mol­ecules of are −66.8 (3) and 70.3 (3)°. The sulfonyl and the aniline benzene rings are oriented at angles of 44.1 (1) and 39.7 (1)° in the two mol­ecules. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into dimers.

N-{(2S)-3-Hydroxy-4-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-1-phenyl-2-butyl}-4-methylbenzenesulfonamide

The thia­diazoyl and sulfonyl-benzene rings in the title compound, C20H23N3O3S3, are aligned to the same side of the mol­ecule, forming a twisted ‘U’ shape [dihedral angle = 77.6 (5)°]. The benzyl-benzene ring is orientated in the opposite direction from the mol­ecule but projects approximately along the same axis as the other rings [dihedral angle between benzene rings = 28.2 (5)°] so that, overall, the mol­ecule has a flattened shape. The hy­droxy and amine groups are almost syn which enables the formation of inter­molecular hy­droxy-OH⋯N(thia­diazo­yl) and amine-H⋯O(sulfon­yl) hydrogen bonds leading to a supra­molecular chain aligned along the a axis.

N′-[(1E,2E)-1-(2-Phenylhydrazin-1-ylidene)-1-(phenylsulfonyl)propan-2-ylidene]benzohydrazide

The configuration about each C=N bond in the title compound, C22H20N4O3S, is E. While to a first approximation the phenyl­hydrazin-1-yl­idene and benzohydrazide residues are coplanar, in part due to the presence of an intra­molecular N—H⋯N hydrogen bond, significant twists are evident in the orientations of the hydrazine [N—N—C—C torsion angle = −170.74 (11)°] and benzoyl benzene [N—C—C—C = −21.72 (18)°] rings. The sulfonyl benzene ring occupies a position almost normal to the rest of the mol­ecule [C—S—C—N = −92.28 (10)°]. Centrosymmetric aggregates mediated by pairs of hydrazide–sulfonyl N—H⋯O hydrogen bonds are the predominant packing motif in the crystal. These are connected into linear supra­molecular chains via C—H⋯O inter­actions which are, in turn, linked into layers in the ac plane via C—H⋯π inter­actions. Connections between layers along the b-axis direction are of the π–π type and occur between centrosymmetrically related hydrazine-bound benzene rings [centroid–centroid separation = 3.7425 (9) Å].

4-Chloro-N-phenylbenzenesulfonamide

In the crystal of the title compound, C12H10ClNO2S, the asymmetric unit contains two independent mol­ecules. The N—C bonds in the C—SO2—NH—C segments have gauche torsions with respect to the S=O bonds. The mol­ecules are twisted at the S atoms with C—SO2—NH—C torsion angles of −53.8 (3) and −63.4 (3)° in the two mol­ecules. The benzene rings are tilted relative to each other by 69.1 (1) and 82.6 (1)°. The dihedral angle between the sulfonyl benzene rings of the two independent mol­ecules is 23.7 (2)°. The crystal structure features inversion-related dimers linked by N—H⋯O hydrogen bonds.

2-Methyl-N-(4-nitrobenzoyl)benzenesulfonamide

In the title compound, C14H12N2O5S, the conformation of the N—C bond in the C—SO2—NH—C(O) segment has gauche torsions with respect to the S=O bonds. The mol­ecule is twisted at the S atom, the C—S(O2)—NH—C(O) torsion angle being 61.8 (5)°. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 86.8 (2)° and that between the sulfonyl and the benzoyl benzene rings is 83.8 (2)°. In the crystal, mol­ecules are linked into zigzag chains along the a axis via N—H⋯O hydrogen bonds.

4-Methyl-N-(4-nitrobenzoyl)benzenesulfonamide

In title compound, C14H12N2O5S, the dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 81.5 (2)° and that between the sulfonyl and the benzoyl benzene rings is 89.8 (1)°. In the crystal, mol­ecules are linked into chains along the b axis via inter­molecular N—H⋯O hydrogen bonds. C—H⋯O inter­actions are also observed.

Etoricoxibium picrate.

In the cation of the title salt (systematic name: 5-{5-chloro-3-[4-(methyl­sulfon­yl)phen­yl]-2-pyrid­yl}-2-methyl­pyridinium 2,4,6-trinitro­phenolate), C18H16ClN2O2S+·C6H2N3O7 −, the mean planes of the two pyridine rings in the bipyridine unit are twisted by 33.9 (2)° with respect to each other. The dihedral angles between the mean planes of the sulfonyl­benzene ring and the chloro­pyridine and methyl­pyridine rings are 51.2 (0) and 49.3 (9)°, respectively. The picrate anion inter­acts with the protonated N atom through a bifurcated N—H⋯(O,O) hydrogen bond, forming an R 1 2(6) ring motif with the N atom from the methyl­pyridine group of an adjacent cation. N—H⋯O hydrogen bonds, weak C—H⋯O and π–π stacking inter­actions [centroid–centroid distances = 3.8192 (9)and 3.6749 (9)] occur in the crystal packing, creating a two-dimensional network structure along [110].

4-Chloro-N-(4-chlorophenyl)-2-methylbenzenesulfonamide

In the title compound, C13H11Cl2NO2S, the conformations of the N—C bonds in the C—SO2—NH—C segment have gauche torsions with respect to the S=O bonds. Further, the conformation of the N—H bond is syn to the ortho-methyl group in the sulfonyl benzene ring. The torsion angle of the C—SO2—NH—C segment in the mol­ecule is 55.0 (2)°. The two benzene rings are tilted relative to each other by 67.0 (1)°. In the crystal, inter­molecular N–H⋯O hydrogen bonds link the mol­ecules into infinite column-like chains.

N-(4-Chlorobenzoyl)-2-methylbenzenesulfonamide

The asymmetric unit of the title compound, C14H12ClNO3S, contains two independent mol­ecules. The conformations of the N—C bonds in the C—SO2—NH—C(O) segments have gauche torsions with respect to the S=O bonds. The mol­ecules are twisted at the S atoms with torsion angles of −54.2 (2) and 63.8 (2)° in the two mol­ecules. The dihedral angles between the sulfonyl benzene rings and the —SO2—NH—C—O segments are 85.0 (1) and 87.0 (1)°. Furthermore, the dihedral angles between the sulfonyl and benzoyl benzene rings are 89.4 (1) and 82.4 (1)° in the two mol­ecules. In the crystal, mol­ecules are linked by N—H⋯O(S) hydrogen bonds.

4-Chloro-N-(3-chlorobenzoyl)benzenesulfonamide monohydrate

In the title compound, C13H9Cl2NO3S·H2O, the conformation of the C=O bond is syn to the meta-Cl group in the benzoyl ring. The mol­ecules are twisted at the S—N bond with a C—S—N—C torsion angle of 72.9 (2)°. The dihedral angle between the sulfonyl benzene ring and the S—NH—C—O segment is 77.8 (1)° and that between the sulfonyl and benzoyl benzene rings is 80.5 (1)°. In the crystal, mol­ecules are linked into a two-dimensional network parallel to (100) by N—H⋯O and O—H⋯O hydrogen bonds.

N-(4-Methylbenzoyl)benzenesulfonamide

In the title compound, C14H13NO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. The dihedral angle between the sulfonyl benzene ring and the S—N—C—O segment (r.m.s. deviation = 0.039 Å) is 77.1 (1)° and that between the sulfonyl and benzoyl benzene rings is 71.9 (1)°.

4-Chloro-N-(4-methylbenzoyl)benzenesulfonamide

In the title compound, C14H12ClNO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. The mol­ecule is twisted at the S atom with a torsion angle of 69.0 (2)°. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 77.2 (1)° and that between the sulfonyl and the benzoyl benzene rings is 89.5 (1)°. In the structure, mol­ecules are linked into chains via N—H⋯O hydrogen bonds, forming inversion dimers.

4-Methyl-N-(2-methylbenzoyl)benzenesulfonamide

In the title compound, C15H15NO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. Further, the conformation of the C=O bond is syn to the ortho-methyl group in the benzoyl ring. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 87.1 (1)° and that between the sulfonyl and the benzoyl benzene rings is 58.2 (1)°. In the crystal structure, mol­ecules are linked by pairs of N—H⋯O(S) hydrogen bonds, forming inversion dimers.

4-Methyl-N-(4-methylbenzoyl)benzenesulfonamide

In the title compound, C15H15NO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 84.9 (1)° and that between the sulfonyl and the benzoyl benzene rings is 89.0 (1)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur.

2-Chloro-N-(4-methylbenzoyl)benzenesulfonamide

In the title compound, C14H12ClNO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 89.4 (1)° and that between the sulfonyl and benzoyl benzene rings is 89.1 (2)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

4-Chloro-N-(2-chlorobenzoyl)benzenesulfonamide

In the structure of the title compound, C13H9Cl2NO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. The mol­ecule is twisted at the S atom with a torsion angle of 65.7 (2)°. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 88.5 (1)°, and that between the sulfonyl and the benzoyl benzene rings is 58.0 (1)°. In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers.

4-Chloro-N-(4-chlorobenzoyl)benzenesulfonamide

In the title compound, C13H9Cl2NO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. The mol­ecule is twisted at the S atom with a torsion angle of 67.5 (3)°. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 79.0 (1)° and that between the sulfonyl and benzoyl benzene rings is 85.6 (1)°. In the crystal, mol­ecules are linked by N—H⋯O(S) hydrogen bonds with graph-set descriptor C(4) along the [010] direction.

N-Benzoyl-4-chlorobenzenesulfonamide

The asymmetric unit of the title compound, C13H10ClNO3S, contains two independent mol­ecules. The mol­ecules have C—S—N—C torsion angles of −70.0 (2) and 61.3 (2)° for mol­ecules 1 and 2, respectively. The dihedral angles between the sulfonyl benzene rings and the –SO2—NH—C—O segments are 72.0 (1) and 77.3 (1)° for mol­ecules 1 and 2, respectively, and the dihedral angles between the sulfonyl and the benzoyl benzene rings are 62.8 (1) and 78.6 (1)°, respectively. In the crystal, mol­ecules 1 and 2 are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers.

2-Methyl-N-(4-methylbenzoyl)benzenesulfonamide

The asymmetric unit of the title compound, C15H15NO3S, contains two independent mol­ecules. The conformations of the N—C bonds in the C—SO2—NH—C(O) segments have gauche torsions with respect to the SO bonds. Further, the mol­ecules are twisted at the S atoms with torsion angles of −53.1 (2) and 61.2 (2)° in the two mol­ecules. The dihedral angles between the sulfonyl benzene rings and the —SO2—NH—C—O segments are 86.0 (1) and 87.9 (1)°. Furthermore, the dihedral angles between the sulfonyl and the benzoyl benzene rings are 88.1 (1) and 83.5 (1)° in the two mol­ecules. In the crystal, mol­ecules are linked by N—H⋯O(S) hydrogen bonds.