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Crystal structure of N-allyl-4-methyl-benzene-sulfonamide.

ABSTRACT: The title compound, C10H13NO2S, was synthesized by a nucleophilic substitution reaction between allyl amine and p-toluene-sulfonyl chloride. The sulfonate S-O bond lengths are 1.4282 (17) and 1.4353 (17) Å, and the C-N-S-C torsion angle involving the sulfonamide moiety is -61.0 (2)°. In the crystal, centrosymmetric dimers of the title compound are present via inter-molecular N-H⋯O hydrogen bonds between sulfonamide groups. These dimers are linked into ribbons along the c-axis direction through offset π-π inter-actions.

SUBMITTER: Patel ZS

PROVIDER: S-EPMC6072992 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure of N-(1-allyl-3-chloro-1H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

Project description:The 3-chloro-1H-indazole system in the title mol-ecule, C17H16ClN3O2S, is almost planar, with the largest deviation from the mean plane being 0.029?(2)?Å for one of the N atoms. This system is nearly perpendicular to the allyl chain, as indicated by the C-C-N-N torsion angle of -90.1?(6)° between them. The allyl group is split into two fragments, the major component has a site occupancy of 0.579?(7). The indazole system makes a dihedral angle of 47.53?(10)° with the plane through the benzene ring. In the crystal, mol-ecules are connected by N-H?O and C-H?O hydrogen bonds, forming a three-dimensional network.

| S-EPMC4186064 | biostudies-literature

Crystal structure of 4-methyl-N-propyl-benzene-sulfonamide.

Project description:The crystal structure of the title sulfonamide, C10H15NO2S, comprises two mol-ecules 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 mol-ecules in the asymmetric unit), and S-N bond lengths of 1.618?(2) and 1.622?(3)?Å, respectively. When both mol-ecules are viewed down the N-S bond, the propyl group is gauche to the toluene moiety. In the crystal structure, mol-ecules of the title compound are arranged in an intricate three-dimensional network that is formed via inter-molecular C-H?O and N-H?O hydrogen bonds. The crystal structure was refined from a crystal twinned by inversion.

| S-EPMC7336776 | biostudies-literature

Crystal structure of N,N-diisopropyl-4-methyl-benzene-sulfonamide.

Project description:The synthesis of the title compound, C13H21NO2S, is reported here along with its crystal structure. This compound crystallizes with two mol-ecules in the asymmetric unit. The sulfonamide functional group of this structure features S=O bond lengths ranging from 1.433?(3) to 1.439?(3)?Å, S-C bond lengths of 1.777?(3) and 1.773?(4)?Å, and S-N bond lengths of 1.622?(3) and 1.624?(3)?Å. When viewing the mol-ecules down the S-N bond, the isopropyl groups are gauche to the aromatic ring. On each mol-ecule, two methyl hydrogen atoms of one isopropyl group are engaged in intra-molecular C-H?O hydrogen bonds with a nearby sulfonamide oxygen atom. Inter-molecular C-H?O hydrogen bonds and C-H?? inter-actions link mol-ecules of the title compound in the solid state.

| S-EPMC7336799 | biostudies-literature

Crystal structure of 4-methyl-N-(4-methyl-benz-yl)benzene-sulfonamide.

Project description:The title compound, C15H17NO2S, was synthesized via a substitution reaction between 4-methyl-benzyl-amine and p-toluene-sulfonyl chloride. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules, forming ribbons running along the b-axis direction. One of the aromatic rings hosts two inter-molecular C-H⋯π inter-actions that link these hydrogen-bonded ribbons into a three-dimensional network.

| S-EPMC7001832 | biostudies-literature

N-(2-Allyl-4-eth-oxy-2H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

Project description:The indazole ring system of the title compound, C19H21N3O3S, is almost planar (r.m.s. deviation = 0.0192?Å) and forms dihedral angles of 77.99?(15) and 83.9?(3)° with the benzene ring and allyl group, respectively. In the crystal, centrosymmetrically related mol-ecules are connected by pairs of N-H?O hydrogen bonds into dimers, which are further linked by C-H?O hydrogen bonds, forming columns parallel to the b axis.

| S-EPMC4011273 | biostudies-literature

N-(1-Allyl-1H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

Project description:The asymmetric unit of the title compound, C17H17N3O2S, contains two independent mol-ecules linked by an N-H?O hydrogen bond. The mol-ecules show different conformations. In the first mol-ecule, the fused five- and six-membered ring system is almost perpendicular to the plane through the atoms forming the allyl group, as indicated by the dihedral angle of 85.1?(4)°. The dihedral angle with the methyl-benzene-sulfonamide group is 78.8?(1)°. On the other hand, in the second mol-ecule, the dihedral angles between the indazole plane and the allyl and methyl-benzene-sulfonamide groups are 80.3?(3) and 41.5?(1)°, respectively. In the crystal, mol-ecules are further linked by N-H?N and C-H?O hydrogen bonds, forming a three-dimensional network.

| S-EPMC3885088 | biostudies-other

Crystal structures of N-(3-fluoro-benzo-yl)benzene-sulfonamide and N-(3-fluoro-benzo-yl)-4-methyl-benzene-sulfonamide.

Project description:The crystal structures of two N-(aryl-sulfon-yl)aryl-amides, namely N-(3-fluoro-benzo-yl)benzene-sulfonamide, C13H10FNO3S, (I), and N-(3-fluoro-benzo-yl)-4-methyl-benzene-sulfonamide, C14H12FNO3S, (II), are described and compared with related structures. The dihedral angle between the benzene rings is 82.73 (10)° in (I) compared to 72.60 (12)° in (II). In the crystal of (I), the mol-ecules are linked by C-H⋯O and C-H⋯π inter-actions, resulting in a three-dimensional grid-like architecture, while C-H⋯O inter-actions lead to one-dimensional ribbons in (II). The crystals of both (I) and (II) feature strong but non-structure-directing N-H⋯O hydrogen bonds with R 2 (2)(8) ring motifs. The structure of (I) also features π-π stacking inter-actions.

| S-EPMC4910323 | biostudies-literature

N-(1-Allyl-3-chloro-4-eth-oxy-1H-indazol-5-yl)-4-methyl-benzene-sulfonamide.

Project description:In the title compound, C19H20ClN3O3S, the benzene ring is inclined to the indazole ring system by 51.23?(8)°. In the crystal, mol-ecules are linked by pairs of N-H?O hydrogen bonds, forming inversion dimers which stack in columns parallel to [011]. The atoms in the allyl group are disordered over two sets of sites with an occupancy ratio of 0.624?(8):0.376?(8).

| S-EPMC4051038 | biostudies-literature

Crystal structure of N-(3-chloro-1-methyl-1H-indazol-5-yl)-4-meth-oxy-benzene-sulfonamide.

Project description:In the title compound, C15H14ClN3O3S, the dihedral angle between the planes of the indazole ring system (r.m.s. deviation = 0.007?Å) and the benzene ring is 89.05?(7)°. The meth-oxy C atom deviates from its attached ring by 0.196?(3)?Å. In the crystal, inversion dimers linked by pairs of N-H?O hydrogen bonds generate R 2 (2)(8) loops. The dimers are connected into [010] chains by C-H?O inter-actions.

| S-EPMC4186104 | biostudies-literature

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

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