
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
Author(s) -
Alley Steven,
Gallagher John F.,
Hooper Vincent M.,
Kenny Peter T. M.,
Lough Alan J.
Publication year - 2005
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s010827010501783x
Subject(s) - thiazole , chemistry , hydrogen bond , intramolecular force , thiophene , moiety , stereochemistry , molecule , amide , crystallography , intermolecular force , ferrocene , organic chemistry , electrochemistry , electrode
The conformations and hydrogen bonding in the thiophene and thiazole title compounds, [Fe(C 5 H 5 )(C 20 H 14 NO 3 S)], (I), and [Fe(C 5 H 5 )(C 19 H 17 N 2 O 3 S)], (II), are discussed. The sequence (C 5 H 4 )–(C 6 H 4 )–(CONH)–(C 4 H 2 S)–(CO 2 Me) of rings and moieties in (I) is close to being planar; all consecutive interplanar angles are less than 10°. An intramolecular N—H⋯O=C ester 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 C ar —H⋯O=C ester/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 (C 6 H 4 ) and thiazole (C 3 NS) rings is 8.1 (2)° in one molecule and 27.66 (14)° in the other. Intermolecular N—H⋯O=C ester hydrogen bonds [N⋯O = 2.972 (4) and 2.971 (3) Å], each augmented by a C phenylene —H⋯O=C ester interaction [3.184 (5) and 3.395 (4) Å], form motifs with graph set (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.