Characterization of New Acetic Acid Solvates and Studies of Acetic Acid Binding Interactions

A report submitted by Daniel Adsmond to the Research and Creative Productions Committee in January of 1998 on the binding interactions in acetic acid solvates with specific emphasis on binding of acetic acid to sulfa drugs

4-[(2-Hy­droxy­benzyl­idene)amino]-N-(5-methyl­isoxazol-3-yl)benzene­sulfonamide: a monoclinic polymorph

The title compound, C17H15N3O4S, is a monoclinic polymorph with space group P21/c of the previously reported triclinic form in P [Subashini et al. (2009 ▶). J. Chem. Crystallogr. 39, 112–116]. In both polymorphs, intra­molecular O—H⋯N hydrogen bonds and dimer formation via a pair of inter­molecular N—H⋯N hydrogen bonds with an R 2 2(8) motif are observed. The two polymorphs differ in the next level of supra­molecular organization involving C—H⋯O hydrogen bonds with varied packing and different conformations

N-(2-Chloro­phenyl­sulfon­yl)-2,2-dimethyl­propanamide

In the title compound, C11H14ClNO3S, the C—S—N—C torsion angle is −61.69 (17)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur, generating R 2 2(8) loops

N-(2-Methyl­phenyl­sulfon­yl)propanamide

In the title compound, C10H13NO3S, the conformations of the N—H and C=O bonds of the SO2—NH—CO—C segment are anti to each other, while the amide H atom is syn with respect to the ortho-methyl group in the benzene ring. The C—S—N—C torsion angle is −66.7 (2)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) hydrogen bonds

4-Chloro-N-(3-methyl­phen­yl)benzene­sulfonamide

In the crystal of the title compound, C13H12ClNO2S, the N—H bond is anti to the meta-methyl group in the aniline ring. The C—SO2—NH—C torsion angle is −57.6 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 84.7 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds

N-(1-Naphth­yl)benzene­sulfonamide

In the title compound, C16H13NO2S, the C—SO2—NH—C torsion angle is −70.1 (2)°. The dihedral angle between the planes of the naphthyl ring system and the phenyl ring is 34.67 (4)°. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O hydrogen bonds into chains along [100]. There are also π–π inter­actions between adjacent naphthyl groups [inter­planar spacing = 3.541 (3) Å] for mol­ecules stacked along [100]

4-Chloro-N-(3,5-dichloro­phenyl)benzene­sulfonamide

In the title compound, C12H8Cl3NO2S, the dihedral angle between the aromatic rings is 87.9 (1)° and the C—S—N—C torsion angle is 77.8 (2)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur

N-(2-Methyl­phenyl­sulfon­yl)acetamide

In the mol­ecular structure of the title compound, C9H11NO3S, the N—H and C=O bonds are anti to each other, while the amide H atom is syn with respect to the ortho-methyl group in the benzene ring. The C—S—N—C torsion angle is −58.2 (2)°, indicating a twist in the mol­ecule. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into chains along the c axis

N-(2-Chloro­phenyl­sulfon­yl)acetamide

The asymmetric unit of the title compound, C8H8ClNO3S, contains two independent mol­ecules in which the C—S—N—C torsion angles are −71.7 (3) and 61.2 (3)°. The benzene rings and the SO2—NH—CO—C segments form dihedral angles of 80.2 (1) and 88.1 (2)° in the two independent mol­ecules. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into chains in the b-axis direction

N-(2,6-Dimethyl­phen­yl)-2,4-dimethyl­benzene­sulfonamide

Mol­ecules of the title compound, C16H19NO2S, are bent at the S atom with a C—SO2—NH—C torsion angle of −60.0 (2)°. The dihedral angle between the phenyl­sulfonyl and aniline rings is 41.7 (1)°. In the crystal, mol­ecules are packed into centrosymmetric dimers through pairs of N—H⋯O(S) hydrogen bonds