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Methyl 2-(4-ferrocenylbenzamido)thiophene-3-carboxylate and ethyl 2-(4-ferrocenylbenzamido)-1,3-thiazole-4-acetate, a unique ferrocen
Alley, Steven; Gallagher, John F.; Hooper, Vincent M.; Kenny, Peter T.M.; Lough, Alan J.
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-H...O=Cester hydrogen bond [graph set S(6), N...O = 2.768 (2) Å and N-H...O = 134 (2)°] effects the molecular planarity, and aggregation occurs via hydrogen-bonded chains formed from intermolecular Car-H...O=Cester/amide interactions along [010], with C...O 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-H...O=Cester hydrogen bonds [N...O = 2.972 (4) and 2.971 (3) Å], each augmented by a Cphenylene-H...O=Cester interaction [3.184 (5) and 3.395 (4) Å], form motifs with graph set R¹₂(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.
Keyword(s): Organic chemistry; Chemistry; Crystallography
Publication Date:
2005
Type: Other
Peer-Reviewed: Unknown
Language(s): English
Institution: Dublin City University
Citation(s): Alley, Steven, Gallagher, John F. ORCID: 0000-0003-4130-4556 <https://orcid.org/0000-0003-4130-4556>, Hooper, Vincent M., Kenny, Peter T.M. and Lough, Alan J. (2005) Methyl 2-(4-ferrocenylbenzamido)thiophene-3-carboxylate and ethyl 2-(4-ferrocenylbenzamido)-1,3-thiazole-4-acetate, a unique ferrocen. Acta Crystallographica Section C, 61 (7). pp. 365-369. ISSN 0108-2701
Publisher(s): International Union of Crystallography
File Format(s): application/pdf
Related Link(s): http://doras.dcu.ie/126/1/acta_crys_c_61_7.pdf,
http://dx.doi.org/10.1107/S010827010501783X
First Indexed: 2009-11-05 02:00:17 Last Updated: 2019-02-09 07:05:31