Steven Alley

2-Ferrocenyl-N-(2-ferrocenylbenzo­yl)-N-(4-methyl-2-pyrid­yl)benzamide

The title compound, [Fe2(C5H5)2(C30H22N2O2)], a 2:1 product of the reaction of 2-ferrocenylbenzoic acid and 2-amino-4-methylpyridine, forms a twisted molecular structure in the solid state due to steric effects from the two benzene rings ortho-substituted with ferrocenyl and carbonyl-derived groups. A short intramolecular C—H⋯π interaction is observed involving a substituted η5-C5H4 ring and an ortho H atom of the benzene ring on the opposite side of the molecule. In the crystal structure, there are no classical hydrogen bonds: interactions comprise a short C6—H⋯π(C6) interaction involving substituted benzene rings and two C—H⋯O=C interactions per molecule.

2-Ferrocenyl-N-(6-methyl-2-pyrid­yl)benzamide

The title compound, [Fe(C5H5)(C18H15N2O)], a product of the reaction of 2-ferrocenylbenzoic acid and 2-amino-6-methylpyridine, crystallizes with two dissimilar molecules in the asymmetric unit. In one molecule, the picoline amide group is directed away from the 2-ferrocenylbenzene moiety (anti) whereas in the other, these are proximate (syn). In the crystal structure, molecules aggregate into dimers via cyclic, asymmetric N—H⋯N interactions with graph set R 2 2(8), and are further augmented via intramolecular C—H⋯O=C and interdimer C—H⋯π(arene) interactions. Dimers are linked into chains along the [102] direction via weak C—H⋯O hydrogen bonds.

Methyl 2-(4-ferrocenylbenzamido)thiophene-3-carboxylate and ethyl 2-(4-ferrocenylbenzamido)-1,3-thiazole-4-acetate, a unique ferrocene derivative containing a thiazole moiety

The conformations and hydrogen bonding in the thiophene and thiazole title compounds, [Fe(C5H5)(C20H14NO3S)], (I), and [Fe(C5H5)(C19H17N2O3S)], (II), are discussed. The sequence (C5H4)-(C6H4)-(CONH)-(C4H2S)-(CO2Me) of rings and moieties in (I) is close to being planar; all consecutive interplanar angles are less than 10 degrees . An intramolecular N-H...O=C(ester) hydrogen bond [graph set S6, N...O = 2.768 (2) A and N-H...O = 134 (2) degrees ] effects the molecular planarity, and aggregation occurs via hydrogen-bonded chains formed from intermolecular C(ar)-H...O=C(ester/amide) interactions along [010], with C...O distances ranging from 3.401 (3) to 3.577 (2) A. The thiazole system in (II) crystallizes with two molecules in the asymmetric unit; these differ in the conformation along their long molecular axes; for example, the interplanar angle between the phenylene (C6H4) and thiazole (C3NS) rings is 8.1 (2) degrees in one molecule and 27.66 (14) degrees in the other. Intermolecular N-H...O=C(ester) hydrogen bonds [N...O = 2.972 (4) and 2.971 (3) A], each augmented by a C(phenylene)-H...O=C(ester) interaction [3.184 (5) and 3.395 (4) A], form motifs with graph set R2(1)(7) and generate chains along [100]. The amide C=O groups do not participate in hydrogen bonding. Compound (II) is the first reported ferrocenyl-containing thiazole structure.