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

ABSTRACT: 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.

SUBMITTER: Khan IU

PROVIDER: S-EPMC3007528 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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

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

Acta crystallographica. Section E, Structure reports online 20100731 Pt 8

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 ...[more]

PMID: 21588423

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

Project description: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.

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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.

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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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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.

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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.

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