Synthesis and antibacterial evaluation of some novel imidazole and benzimidazole sulfonamides.

Several new substituted sulfonamide compounds were synthesized and their structures were confirmed by ¹H-NMR, ¹³C-NMR, FT-IR, and mass spectroscopy. The antibacterial activities of the synthesized compounds were screened against standard strains of six Gram positive and four Gram negative bacteria using the microbroth dilution assay. Most of the compounds studied showed promising activities against both types of bacteria.

N,N'-{[Ethane-1,2-diylbis(-oxy)]bis-(ethane-2,1-di-yl)}bis-(4-methyl-benzene-sulfonamide).

The asymmetric unit of the title compound, C(20)H(28)N(2)O(6)S(2), contains one half-mol-ecule, related to the other half by a twofold rotation axis. The two aromatic rings of the mol-ecule make a dihedral angle of 50.91 (7)°.

tert-Butyl 2-(1H-benzimidazol-1-yl)acetate.

In the title compound, C(13)H(16)N(2)O(2), the planes of the benzimidazole ring system and the acetate O-C=O fragment make a dihedral angle of 84.5 (3)°. In the crystal, mol-ecules are connected through C-H⋯N hydrogen bonds to form infinite chains in the [-110] direction.

tert-Butyl 2-(1H-imidazol-1-yl)acetate.

In the title compound, C(9)H(14)N(2)O(2), the imidazole ring and the acetate O-C=O plane make a dihedral angle of 80.54 (12)°. In the crystal, mol-ecules are connected via pairs of C-H⋯O hydrogen bonds, forming centrosymmetric dimers.

1,1'-{2,2'-[1,4-Phenyl-enebis(methyl-ene)]bis-(-oxy)bis-(2,1-phenyl-ene)}diethanone.

The asymmetric unit of the title compound, C(24)H(22)O(4), contains one half-mol-ecule, the other half being generated by a crystallographic center of inversion. The central benzene ring makes a dihedral angle of 72.49 (5)° with the terminal benzene ring.

1,1'-{[1,4-Phenyl-enebis(methyl-ene)]bis-(-oxy)bis-(4,1-phenyl-ene)}diethanone.

The centroid of the central aromatic ring of the title mol-ecule, C(24)H(22)O(4), is located on an inversion center. The dihedral angle between the central and terminal benzene rings is 75.00 (7)°.

1,1'-{[1,4-Phenyl-enebis(methyl-ene)]bis-(-oxy)bis-(3,1-phenyl-ene)}diethanone.

In the title compound, C(24)H(22)O(4), the centroid of the central benzene ring lies on a special position of 2/m site symmetry, while the terminal aromatic rings are located on a mirror plane. The central and terminal benzene rings are perpendic-ular to each other. In the crystal, the mol-ecules are connected via C-H⋯O hydrogen bonds into a three-dimensional polymeric structure.

2-Methyl-3-[(4-methyl-phen-yl)sulfon-yl-oxy]-2-{[(4-methyl-phen-yl)sulfon-yloxy]meth-yl}propyl 4-methyl-benzene-sulfonate.

The title mol-ecule, C(26)H(30)O(9)S(3), adopts an extended conformation whereby two approximately parallel benzene rings [dihedral angle = 8.32 (10)°] are orientated in opposite directions along the pseudo-threefold axis through the central quaternary C atom, while a third ring occupies a position mid-way and face-on to these rings [dihedral angles = 82.28 (10) and 78.

1-Carb-oxy-methyl-3-octylimidazolium bromide.

In the title compound, C(13)H(23)N(2)O(2) (+)·Br(-), the octyl chain has an all-trans conformation. In the crystal, the cations are linked by C-H⋯O bonds into a zigzag chain along the b axis. The bromide anions further link the chains via C-H⋯Br inter-actions into a two-dimensional array parallel to the ab plane.

Imidazo[1,2-b]isoquinoline-5,10-dione.

The title butterfly-shaped mol-ecule, C(11)H(6)N(2)O(2), is folded slightly along the O=C⋯C=O line, the dihedral angle between the two parts being 6.42 (3)°. In the crystal, adjacent mol-ecules are linked through C-H⋯O hydrogen bonds into infinite layers parallel to the ac plane.

1-Tosyl-2-[(1-tosyl-1H-benzimidazol-2-yl)methyl-sulfanyl]-1H-benzimidazole.

In the title compound, C(29)H(24)N(4)O(4)S(3), the two N-tosyl-benzimidazolyl unit are connected through a -S-CH(2)- fragment, the dihedral angle between the benzimidazole rings being 76.09 (5)°. The methyl-thio group is disordered with respect to exchange of the S and C atoms in a 0.