Crystal structure of 4-methyl-2-oxo-2H-chromen-7-yl ferrocenecarboxylate

Abstract

The title mol­ecule, [Fe(C5H5)(C16H11O4)], consists of a ferrocenyl moiety and a 4-methyl­coumarin group linked through an ester unit to one of the cyclo­penta­dienyl (Cp) rings. The two Cp rings are virually parallel, with an angle between the two least-squares planes of 0.74 (16)°. The distances between the FeII atom and the centroids of the two Cp rings are 1.639 (2) and 1.652 (2) Å. The conformation of the ferrocenyl moiety is slightly away from eclipsed. The dihedral angle between the coumarin ring system and the ferrocenyl ester moiety is 69.17 (19)°. π–π stacking inter­actions involving the benzene rings of neighbouring coumarin moieties, with centroid–centroid distances of 3.739 (2) Å, consolidate the crystal packing.

Crystal structure of 2-oxo-2H-chromen-7-yl 4-fluorobenzoate

“…tuents at the 7 position (Ramasubbu et al, 1982;Gnanaguru et al, 1985;Parveen et al, 2011;Ji et al, 2014Ji et al, , 2017. In these structures and those of meta-substituted coumarin esters (Abou et al, 2013;Bibila Mayaya Bisseyou et al, 2013;Yu et al, 2014;Gomes et al, 2016;Ziki et al, 2016Ziki et al, , 2017, the pyrone rings show three long (in the range 1.37-1.46 Å ) and one short (1.32-1.34 Å ) C-C distances, suggesting that the electronic density is preferentially located in the short C-C bond at the pyrone ring. This pattern is clearly repeated for (I) with C2-C3 = 1.332 (5) Å , while C1-C2 = 1.451 (5), C3-C4 = 1.434 (4) and C4-C5 = 1.399 (4) Å .…”

2-Oxo-2H-chromen-7-yl 4-tert-butylbenzoate

“…A CSD search (Web CSD version 5.39; March 9, 2018; Groom et al, 2016) found five coumarin ester structures with substituents at the 7 positions (Ramasubbu et al,1982;Gnanaguru et al, 1985;Parveen et al, 2011;Ji et al, 2014Ji et al, , 2017. In these structures and those of meta-substituted coumarin esters (Abou et al, 2012(Abou et al, , 2013Bibila Mayaya Bisseyou et al, 2013;Yu et al, 2014;Gomes et al, 2016;Ziki et al, 2016Ziki et al, , 2017 Hydrogen-bond geometry (Å , ).…”