Sulfonyl Benzene Rings Research Articles

N-[2-(3,4-Di-meth-oxy-phen-yl)-2-(phenyl-sulfan-yl)eth-yl]-2-(2-fluoro-phen-yl)acetamide.

The title compound, C24H24FNO3S, is an inter-mediate in the synthesis of fluorine containing iso-quinoline alkaloids, which crystallizes in the triclinic space group P with one mol-ecule in the asymmetric unit. The structure presents a racemic mixture of enanti-omers. The C-S-C-C torsion angle between the benzene ring system and the sulfonyl benzene ring is -178.5 (1)°. In the crystal, N-H⋯O hydrogen bonds between neighbouring mol-ecules form chains of mol-ecules along the a-axis direction.

Crystal structure of 2-[2-phenyl-1-(phenyl-sulfon-yl)eth-yl]-1-phenyl-sulfonyl-1H-indole.

In the title compound, C28H23NO4S2, the indole ring system (r.m.s. deviation = 0.007 Å) subtends dihedral angles of 78.69 (13) and 38.97 (13)° with the planes of the N- and C-bonded sulfonyl­benzene rings, respectively, and these two benzene rings are inclined to each other at an angle of 65.45 (16)°. The methyl­ene-linked phenyl ring is twisted at an angle of 81.80 (13)° from the indole ring. The mol­ecular structure features two short intra­molecular C—H⋯O contacts, which both generate S(6) rings. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds and C—H⋯π inter­actions, generating a three-dimensional network.

Crystal structures of 4-meth-oxy-N-(4-methyl-phenyl)benzene-sulfonamide and N-(4-fluoro-phenyl)-4-meth-oxy-benzene-sulfonamide.

Crystal structures of two N-(ar-yl)aryl-sulfonamides, namely, 4-meth-oxy-N-(4-methyl-phen-yl)benzene-sulfonamide, C14H15NO3S, (I), and N-(4-fluoro-phen-yl)-4-meth-oxy-benzene-sulfonamide, C13H12FNO3S, (II), were determined and analyzed. In (I), the benzene-sulfonamide ring is disordered over two orientations, in a 0.516 (7):0.484 (7) ratio, which are inclined to each other at 28.0 (1)°. In (I), the major component of the sulfonyl benzene ring and the aniline ring form a dihedral angle of 63.36 (19)°, while in (II), the planes of the two benzene rings form a dihedral angle of 44.26 (13)°. In the crystal structure of (I), N-H⋯O hydrogen bonds form infinite C(4) chains extended in [010], and inter-molecular C-H⋯πar-yl inter-actions link these chains into layers parallel to the ab plane. The crystal structure of (II) features N-H⋯O hydrogen bonds forming infinite one dimensional C(4) chains along [001]. Further, a pair of C-H⋯O inter-molecular inter-actions consolidate the crystal packing of (II) into a three-dimensional supra-molecular architecture.

2-Chloro-N-(4-meth-oxy-benzo-yl)-benzene-sulfonamide.

In the title compound, C14H12ClNO4S, the dihedral angle between the aromatic rings is 82.07 (1)° and the dihedral angle between the planes defined by the S—N—C=O fragment and the sulfonyl benzene ring is 82.46 (3)°. In the crystal, the mol­ecules are linked into C(4) chains running along [001] by strong N—H⋯O hydrogen bonds. A C—H⋯O intera­ction reinforces the [001] chains: its graph-set symbol is C(7). The chains are cross-linked into (100) sheets by further C—H⋯O inter­actions as C(6) chains along [001]. The structure also features weak π–π stacking inter­actions [centroid–centroid distances = 3.577 (1) and 3.8016 (1) Å].

N-(4-Meth-oxy-benzo-yl)-2-methyl-benzene-sulfonamide.

In the title compound, C15H15NO4S, the dihedral angle between the aromatic rings is 80.81 (1)° and the dihedral angle between the planes defined by the S—N—C=O fragment and the sulfonyl benzene ring is 86.34 (1)°. In the extended structure, dimers related by a crystallographic twofold axis are connected by pairs of both N—H⋯O hydrogen bonds and C—H⋯O inter­actions, which generate R 2 2(8) and R 2 2(14) loops, respectively. A weak aromatic π–π stacking inter­action is also observed [centroid–centroid separation = 3.7305 (3) Å].

N-(4-Meth-oxy-benzo-yl)benzene-sulfon-amide.

In the title compound, C14H13NO4S, the dihedral angle between the aromatic rings is 69.81 (1)°; the dihedral angle between the planes defined by the S—N—C=O segment of the central chain and the sulfonyl benzene ring is 74.91 (1)°. In the crystal, the mol­ecules are linked by weak N—H⋯O hydrogen bonds into C(4) chains running along [100]. The mol­ecules in adjacent chains are linked by weak C—H⋯O inter­actions, generating R 2 2 (16) dimeric pairs. Weak C—H⋯π inter­actions connect the double chains into (001) sheets.

N-[(2-Chlorophenyl)sulfonyl]-3-nitrobenzamide

In the title compound, C13H9ClN2O5S, the dihedral angle between the benzene rings is 74.86 (11)°. The mol­ecule is twisted at the S atom, with a dihedral angle of 82.53 (13)° between the sulfonyl benzene ring and the S—N—C=O segment. In the crystal, mol­ecules are linked into inversion dimers through pairs of N—H⋯O hydrogen bonds, thereby forming R 2 2(8) loops. Mol­ecules are linked into C(7) [010] chains by weak C—H⋯O hydrogen bonds, and C—H⋯π inter­actions are also observed.

N-(2,3-Dichlorophenyl)-2-nitrobenzenesulfonamide

In the title compound, C12H8Cl2N2O4S, the N—C bond in the C—SO2—NH—C segment has gauche torsions with respect to the S=O bonds. Further, the N—H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and also syn to both the ortho- and meta-Cl atoms in the aniline ring. The mol­ecule is twisted at the S—N bond with a torsion angle of 61.15 (18)°. The dihedral angle between the planes of the benzene rings is 68.00 (6)°. The amide H atom exhibits an intra­molecular bifurcated N—H⋯(O,O) hydrogen bond. In the crystal, pairs of N—H⋯O(S) hydrogen bonds link the mol­ecules into inversion dimers with R 2 2(8) motifs.

N-(2,5-Dimethylphenyl)-2-nitrobenzenesulfonamide

In the crystal structure of the title compound, C14H14N2O4S, the N—H bond is syn to the ortho-nitro group in the sulfonyl benzene ring and anti to the ortho- and syn to the meta-methyl groups in the aniline ring. The mol­ecule is twisted at the S—N bond with a torsion angle of 71.41 (18)°. The dihedral angle between the planes of the benzene rings is 51.07 (8)°. In the crystal, pairs of N—H⋯Osulfonamide hydrogen bonds link the mol­ecules into inversion dimers.

N-(2,3-Dimethylphenyl)-2-nitrobenzenesulfonamide

There are two independent mol­ecules in the asymmetric unit of the title compound, C14H14N2O4S. The N—H bonds are syn to the ortho-nitro groups in the sulfonyl benzene rings and anti to the methyl groups in the aniline benzene rings. The mol­ecules are twisted at the S—N bonds with torsion angles of −60.4 (3) and 58.8 (3)° in the two mol­ecules. The dihedral angles between the planes of the sulfonyl and the anilino benzene rings are 53.67 (8) and 56.99 (9)°. The amide H atoms of both mol­ecules are involved in an intra­molecular hydrogen bond, generating an S(7) motif. In the crystal, pairs of N—H⋯O(S) hydrogen bonds link like mol­ecules into inversion dimers.

N-(4-Methylphenyl)-2-nitrobenzenesulfonamide

In the crystal of the title compound, C13H12N2O4S, the conformation of the N—H bond in the –SO2—NH– segment is syn to the ortho-nitro group in the sulfonyl benzene ring. The mol­ecule is twisted at the S—N bond with a torsion angle of 76.55 (18)°. The dihedral angle between the planes of the rings is 72.64 (8)°. In the crystal, mol­ecules are linked by pairs of N—H⋯O(S) hydrogen bonds to form inversion dimers.

N-(2-Chlorophenyl)-2-nitrobenzenesulfonamide

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.

N-(3-Nitrobenzoyl)benzenesulfonamide

In the title compound, C13H10N2O5S, the C=O bond in the —SO2—NH—CO— segment is anti to the meta-nitro group in the benzoyl ring, while the N—C bond has gauche torsions with respect to the S=O bonds. The molecule is twisted at the N atom with a dihedral angle of 79.9 (2)° between the sulfonyl benzene ring and the —SO2—NH—CO— segment. Furthermore, the dihedral angle between the benzeneline rings is 86.9 (2)°. In the structure, the mol­ecules are linked into helical chains along the b axis via N—H⋯O hydrogen bonds.

N-(3-Chlorobenzoyl)-2-nitrobenzenesulfonamide

In the title compound, C13H9ClN2O5S, the N—C bond in the C—SO2—NH—C segment has a gauche torsion with respect to the S=O bonds. The conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn, and that between the C=O and the meta-Cl atom in the benzoyl ring is anti. The mol­ecule is twisted at the S—N bond, with a torsion angle of 65.41 (38)°. The dihedral angle between the sulfonyl benzene ring and the –SO2—NH—C—O segment is 75.0 (1)°, and that between the sulfonyl and the benzoyl benzene ring is 89.1 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) hydrogen bonds.

N-(3-Methylbenzoyl)-2-nitrobenzenesulfonamide

In the title compound, C14H12N2O5S, the conformation between the N—H group and the ortho-nitro group in the sulfonyl benzene ring is syn and that between the C=O and meta-methyl groups in the benzoyl ring is anti. The mol­ecule is twisted at the S—N bond with a torsion angle of 64.3 (2)°. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 75.73 (7)° and that between the sulfonyl and benzoyl benzene rings is 89.5 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) hydrogen bonds.

N-Benzoyl-2-nitrobenzenesulfonamide

In the title compound, C13H10N2O5S, the N—C bond in the C—SO2—NH—C segment has gauche torsion angles with respect to the S=O bonds. The conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn. The mol­ecule is twisted at the S—N bond with a torsion angle of −63.4 (2)°. The sulfonyl benzene ring is tilted by 77.1 (1)° relative to the —SO2—NH—C—O segment. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 88.6 (1)°. In the crystal, pairs of N—H⋯O(S) hydrogen bonds link the mol­ecules into inversion dimers, which are linked by weak C—H⋯O and C—H⋯π inter­actions along the b axis.

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

In the title compound, C15H16ClNO2S, the conformation of the N—C bond in the C—SO2—NH—C segment is gauche with respect to the S=O bonds. Further, the N—H bond in the C—SO2—NH—C segment is syn with respect to the meta-methyl group in the aniline benzene ring and the ortho-methyl group in the sulfonyl benzene ring. The C—SO2—NH—C torsion angle is −49.72 (18)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 71.6 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

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

In the title compound, C13H10Cl3NO2S, the N—C bond in the C—SO2—NH—C segment forms trans and gauche torsion angles with respect to the S=O bonds. Further, the N—H bond in the C—SO2—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—SO2—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, mol­ecules are linked into chains along the c-axis direction by inter­molecular N—H⋯O hydrogen bonds.

2,4-Dichloro-N-(2,3-dichlorophenyl)benzenesulfonamide

In the title compound, C12H7Cl4NO2S, the conformation of the N—C bond in the C—SO2—NH—C segment is gauche with respect to the S=O bonds. Further, the N—H bond in the C—SO2—NH—C segment is syn with respect to the ortho-Cl atoms in the aniline and sulfonyl benzene rings. The C—SO2—NH—C torsion angle is −51.98 (18)°. The sulfonyl and aniline benzene rings are tilted by 67.7 (1)° relative to each other. An intra­molecular N—H⋯Cl hydrogen bond occurs.

4-Chloro-N-(2,5-dimethylphenyl)-2-methylbenzenesulfonamide

The asymmetric unit of the title compound, C15H16ClNO2S, 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 mol­ecules. 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 mol­ecules. In the crystal, inter­molecular N—H⋯O hydrogen bonds link each of the mol­ecules into centrosymmetric dimers.