Sofiane Bouacida

Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus

Several new highly functionalized imidazolium derivatives were synthesized, via appropriate synthetic routes, using imidazole, 1-methylimidazole and 2-phenyl-1-methylimidazole as key intermediates. The antibacterial activity of the prepared compounds was evaluated against: Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella thipymurium using disk-diffusion and MIC methods. Crystal X-ray structures are reported for six compounds.

Methyl 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetate

In the crystal of the title compound, C7H9N3O4, molecules are linked by weak C—H⋯O hydrogen bonds into chains along the a-axis direction. The dihedral angle between the ring and the nitro group is 3.03 (6), while that between the ring and the acetate group is 85.01 (3)°.

4,5-Dibromo-1,2-dimethyl-1H-imidazol-3-ium bromide.

In the title salt, C5H7Br2N2 +·Br−, the cation and anion are connected by an N—H⋯Br hydrogen bond. In the crystal, there are intercalated layers parallel to (10-2) in which bromide ions are located between the cations. Weak intermolecular C—H⋯Br hydrogen bonds are also observed.

2-Amino-3-carb-oxy-pyrazin-1-ium nitrate monohydrate.

In crystal structure of the title compound, C5H6N3O2 +·NO3 −·H2O, intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds link the cations, anions and water molecules into ribbons extending in [10]. Weak intermolecular C—H⋯O hydrogen bonds further link these ribbons into sheets parallel to ( 3).

3,4-Dimethylanilinium chloride monohydrate

The crystal structure of the title compound, C8H12N+·Cl−·H2O, consists of hydrophobic layers of dimethylanilinium cations parallel to the bc plane alternated by hydrophilic layers of chloride anions and water molecules. The layers are linked by N—H⋯O and N—H⋯Cl hydrogen bonds involving the ammonium groups of the cations. The cohesion of the ionic structure is further stabilized by O—H⋯Cl hydrogen-bonding interactions.

Bis[4-(di­methyl­amino)­pyridinium] tetra­chlorido­cuprate(II)

The asymmetric unit of the title salt, (C7H11N2)2[CuCl4], comprises half a tetrahedral tetrachloridocuprate anion, being located on a twofold axis, and a protonated 4-(dimethylamino)pyridine cation. The geometry around the CuII ion is highly distorted with the range of Cl—Cu—Cl angles being 94.94 (1)–141.03 (1)°. The crystal structure is stabilized by N—H⋯Cl and C—H⋯Cl hydrogen bonds. In the three-dimensional network, cations and anions pack in the lattice so as to generate chains of [CuCl4]2− anions separated by two orientations of cation layers, which are interlocked through π–π stacking contacts between pairs of pyridine rings, with centroid–centroid distances of 3.7874 (7) Å.

(E)-1-[(2,4,6-Tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol.

The title azo molecule, C16H9Br3N2O, adopts a trans conformation with respect to the azo N=N double bond. An intramolecular O—H⋯N hydrogen bond forms an S(6) ring motif. The dihedral angle between the naphthalene ring system and the benzene ring is 33.80 (16)°. In the crystal, molecules are stacked in columns along the a axis by π–π interactions [centroid–centroid distances = 3.815 (3) and 3.990 (3) Å].

2-Hy­droxy­methyl-1,3-dimethyl­imidazolium iodide

The crystal packing of the title compound, C6H11N2O+·I−, can be described as intercalated layers lying parallel to (010), with the iodide ions located between the cations. A weak intramolecular C—H⋯O hydrogen bond occurs within the cation. In the crystal, intermolecular O—H⋯I hydrogen bonds result in the formation of a three-dimensional network and reinforce the cohesion of the ionic structure.

2-(2-Chloro-6,7-dimethyl­quinolin-3-yl)-2,3-dihydro­quinolin-4(1H)-one

In the title molecule, C20H17ClN2O, the dihedral angle between the mean plane of the quinoline ring system and the benzene ring of the dihydroquinolinone moiety is 57.84 (8)°. In the crystal, molecules are linked into centrosymmetric dimers via pairs of intermolecular N—H⋯N hydrogen bonds. These dimers are further stabilized by weak π–π stacking interactions between pyridine rings with a centroid–centroid distance of 3.9414 (12) Å.

Bis[3‐acetyl‐6‐methyl‐2H‐pyran‐2,4(3H)‐dionato]bis­(dimethyl sulfoxide)copper(II)

Laboratoire d0Electrochimie des Matériaux Moléculaires et Complexes, Département de Génie des Procédés, Faculté des Science de l0Ingénieur, Université Farhat Abbes de Setif, DZ-19000 Sétif, Algeria, Département de Chimie, Faculté des Sciences et Sciences de l0Ingénieur, Université A. Mira de Béjaia, Route Targua Ouzmour 06000 Béjaia, Algeria, and Laboratoire de Chimie Moléculaire, du Contrôle de l0Environnement et de Mesures Physico-Chimiques, Département de Chimie, Faculté des Sciences, Université Mentouri 25000, Constantine, Algeria