Ferrocene compounds: methyl 1'-aminoferrocene-1-carboxylate.
The title compund, [Fe(C(5)H(6)N)(C(7)H(7)O(2))], features one strong intermolecular hydrogen bond of the type N-H...O=C [N...O = 3.028 (2) A] between the amine group and the carbonyl group of a neighbouring molecule, and vice versa, to form a centrosymmetric dimer. Furthermore, the carbonyl group acts as a double H-atom acceptor in the formation of a second, weaker, hydrogen bond of the type C-H...O=C [C...O = 3.283 (2) A] with the methyl group of the ester group of a second neighbouring molecule at (x, -y - 1/2, z - 1/2). The methyl group also acts as a weak hydrogen-bond donor, symmetry-related to the latter described C-H...O=C interaction, to a third molecule at (x, -y - 1/2, z + 1/2) to form a two-dimensional network. The cyclopentadienyl rings of the ferrocene unit are parallel to each other within 0.33 (3) degrees and show an almost eclipsed 1,1'-conformation, with a relative twist angle of 9.32 (12) degrees . The ester group is twisted slightly [11.33 (8) degrees ] relative to the cylopentadienyl plane due to the above-mentioned intermolecular hydrogen bonds of the carbonyl group. The N atom shows pyramidal coordination geometry, with the sum of the X-N-Y angles being 340 (3) degrees .
Förster
Christoph
C
Institute of Inorganic and Analytical Chemistry, Johannes Gutenberg University of Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.
Siebler
Daniel
D
Heinze
Katja
K
D002264:Carboxylic Acids / Q000737:chemistry*; D019281:Dimerization; D005296:Ferrous Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation
C504075:1'-aminoferrocene-1-carboxylic acid; D002264:Carboxylic Acids; D005296:Ferrous Compounds