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N-{4-[(3,4-Dimethyl-phen-yl)(eth-yl)sulfamo-yl]phen-yl}-N-ethyl-acetamide.

ABSTRACT: When viewed down the central S?N axis of the title compound, C(20)H(26)N(2)O(3)S, it is apparent that the mol-ecule adopts a gauche conformation with all O atoms lying to one side of the central benzene ring; the carbonyl O atom is directed away from the central ring and the N-bound ethyl groups lie to one side of the mol-ecule. Supra-molecular helical chains aligned along the b axis and sustained by C-H?O contacts feature in the crystal packing. These are consolidated in the three-dimensional structure by C-H?? inter-actions.

SUBMITTER: John P

PROVIDER: S-EPMC3011401 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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N-{4-[(3,4-Dimethyl-phen-yl)(eth-yl)sulfamo-yl]phen-yl}-N-ethyl-acetamide.

John Peter P Khizar Saima S Khan Islam Ullah IU Sharif Shahzad S Tiekink Edward R T ER

Acta crystallographica. Section E, Structure reports online 20101113 Pt 12

When viewed down the central S⋯N axis of the title compound, C(20)H(26)N(2)O(3)S, it is apparent that the mol-ecule adopts a gauche conformation with all O atoms lying to one side of the central benzene ring; the carbonyl O atom is directed away from the central ring and the N-bound ethyl groups lie to one side of the mol-ecule. Supra-molecular helical chains aligned along the b axis and sustained by C-H⋯O contacts feature in the crystal packing. These are consolidated in the three-dimensional s ...[more]

PMID: 21589450

Similar Datasets

N-{4-[(3,4-Dimethyl-phen-yl)sulfamo-yl]phen-yl}acetamide.

Project description:Two independent mol-ecules comprise the asymmetric unit of the title compound, C(16)H(18)N(2)O(3)S. Small but significant twists about the (S)N-C and S-C bonds differentiate the mol-ecules but the most obvious difference is found in the relative orientation of the meta-methyl groups, which lie on opposite sides of the mol-ecules. Overall, both mol-ecules adopt a U shape but with significant twisting evident, particularly in the second independent mol-ecule [dihedral angles between benzene rings = 63.90?(13) and 35.78?(11)°]. In the crystal, N-H?O hydrogen bonds lead to supra-molecular chains with a tubular topology propagating in [100] and C-H?O contacts cross-link the chains.

| S-EPMC3007528 | biostudies-literature

N-(3,4-Dimethyl-phen-yl)acetamide.

Project description:The conformation of the N-H bond in the title compound (34DMPA), C(10)H(13)NO, is syn to the 3-methyl substituent in the aromatic ring, in contrast to the anti conformation observed with respect to the 3-chloro substituent in N-(3,4-dichloro-phen-yl)acetamide (34DCPA). The asymmetric unit of the structure contains three mol-ecules. The bond parameters in 34DMPA are similar to those in 34DCPA, N-(2,6-dimethyl-phen-yl)acetamide, N-(3,5-dimethyl-phen-yl)acetamide and other acetanilides. The mol-ecules in 34DMPA are linked into infinite chains through N-H⋯O hydrogen bonding.

| S-EPMC2914973 | biostudies-literature

N-[4-(Ethyl-sulfamo-yl)phen-yl]acetamide.

Project description:The title compound, C(10)H(14)N(2)O(3)S, crystallized with two mol-ecules (A and B) in the asymmetric unit. The terminal methyl group of the ethyl-sulfonamide moiety in mol-ecule B is disordered over two sets of sites with an occupancy ratio of 0.61?(1):0.39?(1). Both mol-ecules have L-shaped conformations. In mol-ecule A, the dihedral angles between the benzene ring and its ethyl-sulfonamide and methyl-amide substituents are 83.5?(3) and 13.34?(18)°, respectively. Equivalent values for mol-ecule B are 87.9?(3) and 6.32?(16)°, respectively. The C-S-N-C torsion angles are 66.5?(3)° for A and -64.4?(3)° for B, indicating similar twists about the S-N bonds, but in opposite senses. In the crystal, the A mol-ecules are linked by pairs of N(s)-H?O (s = sulfonamide) hydrogen bonds, generating inversion dimers containing R(2) (2)(8) rings, while the B mol-ecules are linked by N(s)-H?O hydrogen bonds into C(10) [100] chains. Finally, N(a)-H?O (a = amide) hydrogen bonds link the A-mol-ecule dimers and B-mol-ecule chains into a three-dimensional network.

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2,2-Dichloro-N-(3,4-dimethyl-phen-yl)acetamide.

Project description:In the title compound, C(10)H(11)Cl(2)NO, the N-H bond is syn to the 3-methyl substituent in the aromatic ring, similar to that observed in N-(3,4-dimethyl-phen-yl)acetamide and to the 3-chloro substituent in 2,2-dichloro-N-(3,4-dichloro-phen-yl)acetamide, and contrasting with the anti conformation observed for the 3-methyl substituent in 2,2,2-trichloro-N-(3,4-dimethyl-phen-yl)acetamide. On the other hand, it is anti to the C=O bond. An inter-molecular N-H?O hydrogen bond links mol-ecules into infinite chains along the b axis.

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2-Chloro-N-(3,4-dimethyl-phen-yl)acetamide.

Project description:The conformation of the C=O bond in the structure of the title compound, C(10)H(12)ClNO, is anti to the N-H bond and to the methyl-ene H atoms in the side chain in both the independent mol-ecules comprising the asymmetric unit. However, the conformation of the N-H bond is syn to the meta-methyl substituent in the aromatic ring of one of the mol-ecules and anti in the other mol-ecule. The two independent mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonding into chains parallel to the b axis.

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2,2,2-Trichloro-N-(3,4-dimethyl-phen-yl)acetamide.

Project description:The conformation of the N-H bond in the title compound, C(10)H(10)Cl(3)NO, is anti to the C=O bond. The amide H atom exhibits both intra-molecular N-H⋯Cl and inter-molecular N-H⋯O hydrogen bonding. The latter inter-actions link the mol-ecules into infinite chains.

| S-EPMC2977724 | biostudies-literature

N-[4-(Benzyl-sulfamo-yl)phen-yl]acetamide.

Project description:A folded conformation is found for the title compound, C(15)H(16)N(2)O(3)S, whereby the benzene rings come into close proximity [centroid-centroid distance = 4.0357?(12)?Å and the dihedral angle between them = 24.37?(10)°]. The amide group is coplanar with the benzene ring to which it is bound [C-C-N-C torsion angle = 11.1?(3)°]. In the crystal packing, two-dimensional arrays in the (101) plane are formed via N-H?O hydrogen bonding.

| S-EPMC3007500 | biostudies-literature

N-[4-(Propyl-sulfamo-yl)phen-yl]acetamide.

Project description:In the title compound, C(11)H(16)N(2)O(3)S, the S atom has a distorted tetra-hedral geometry [maximum deviation: O-S-O = 119.48 (15)°]. The dihedral angles between the benzene ring and its propyl-sulfonamide and methyl-amide substituents are 71.8 (2) and 5.8 (1)°, respectively. In the crystal, mol-ecules are linked by N(m)-H⋯O(s) (m = methyl-amide and s = sulfonamide) hydrogen bonds, forming C(8) chains along the a axis. The two mol-ecule chains are connected by N-H⋯O hydrogen bonds, generating R(3) (2)(18) rings. The crystal packing is further stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

| S-EPMC3274984 | biostudies-literature

N-{4-[(4-Methyl-phen-yl)sulfamo-yl]phen-yl}acetamide.

Project description:The title mol-ecule, C(15)H(16)N(2)O(3)S, has a twisted U-shaped conformation. The twist occurs in the central C-S(=O)(2)N(H)-C unit with the C-S-N-C torsion angle being -58.38?(14)°. The benzene rings lie to the same side of the mol-ecule and form a dihedral angle of 67.03?(10)°. The crystal packing features N-H?O hydrogen bonding, which leads to supra-molecular chains with a tubular topology along the b axis. Intra-molecular C-H?O inter-actions are also observed.

| S-EPMC3007302 | biostudies-literature

N-{4-[(2-Meth-oxy-phen-yl)sulfamo-yl]phen-yl}acetamide.

Project description:In the title compound, C(15)H(16)N(2)O(4)S, the S atom has a distorted tetra-hedral geometry [maximum deviation: O-S-O = 118.25 (7)°]. The two aromatic rings make a dihedral angle of 62.67 (10)° with each other. An intra-molecular N-H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, mol-ecules form centrosymmetric dimers via pairwise N-H⋯O inter-actions, forming an R(2) (2)(8) ring motif, and these dimers are connected by N-H⋯O hydrogen bonds, generating a three-dimensional network. Furthermore, a weak C-H⋯π inter-action helps to reinforce the crystal structure. The O atom in the acetamide group is disordered over two positions with major and minor occupancies of 0.52 (5) and 0.48 (5), respectively.

| S-EPMC3051762 | biostudies-literature

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