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

Notes:

To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

Search: From to Advanced search