Acta Crystallographica Section C

Crystal Structure Communications

Volume 61, Part 7 (July 2005)

metal-organic compounds

fg1846 scheme

Acta Cryst. (2005). C61, m365-m369 [doi:10.1107/S010827010501783X]

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

S. Alley, J. F. Gallagher, V. M. Hooper, P. T. M. Kenny and A. J. Lough

Abstract: 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°. An intramolecular N-HO=C_ester hydrogen bond [graph set S(6), NO = 2.768 (2) Å and N-HO = 134 (2)°] effects the molecular planarity, and aggregation occurs via hydrogen-bonded chains formed from intermolecular C_ar-HO=C_ester/amide interactions along [010], with CO distances ranging from 3.401 (3) to 3.577 (2) Å. 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)° in one molecule and 27.66 (14)° in the other. Intermolecular N-HO=C_ester hydrogen bonds [NO = 2.972 (4) and 2.971 (3) Å], each augmented by a C_phenylene-HO=C_ester interaction [3.184 (5) and 3.395 (4) Å], form motifs with graph set $R_{2}^{1}$ (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.

Formula: [Fe(C₅H₅)(C₂₀H₁₄NO₃S)] and [Fe(C₅H₅)(C₁₉H₁₇NO₃S)]


	Structure factor file (CIF format) (211.4 kbytes) Contains datablock I

	Structure factor file (CIF format) (484.6 kbytes) Contains datablock II

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