Abstract
The substituted cyclo-penta-dienyl ring in the title mol-ecule, [Fe(C5H5)(C18H13ClN)], is nearly coplanar with the phenyl-1-(4-chloro-phen-yl)methanimine substituent, with dihedral angles between the planes of the phenyl-ene ring and the Cp and 4-(chloro-phen-yl)methanimine units of 7.87 (19) and 9.23 (10)°, respectively. The unsubstituted cyclo-penta-dienyl ring is rotationally disordered, the occupancy ratio for the two orientations refined to a 0.666 (7)/0.334 (7) ratio. In the crystal, the mol-ecules pack in 'bilayers' parallel to the ab plane with the ferrocenyl groups on the outer faces and the substituents directed towards the regions between them. The ferrocenyl groups are linked by C-H⋯π(ring) inter-actions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (46.1%), H⋯C/C⋯ H (35.4%) and H⋯Cl/Cl⋯H (13.8%) inter-actions. Thus C-H⋯π(ring) and van der Waals inter-actions are the dominant inter-actions in the crystal packing.
Highlights
The substituted cyclopentadienyl ring in the title molecule, [Fe(C5H5)(C18H13ClN)], is nearly coplanar with the phenyl-1-(4-chlorophenyl)methanimine substituent, with dihedral angles between the planes of the phenylene ring and the Cp and 4-(chlorophenyl)methanimine units of 7.87 (19) and 9.23 (10), respectively
A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from HÁ Á ÁH (46.1%), HÁ Á ÁC/CÁ Á Á H (35.4%) and HÁ Á ÁCl/ClÁ Á ÁH (13.8%) interactions
C—HÁ Á Á(ring) and van der Waals interactions are the dominant interactions in the crystal packing
Summary
Compounds containing metallocene building units, and ferrocene derivatives, have been studied extensively both in academic and industrial settings (Santos et al, 2017; Singh et al, 2019; Ong & Gasser, 2020). A wide range of therapeutic activities is associated with ferrocenyl Schiff bases, which have shown exceptionally high activities against pathogenic microbes (Chohan & Praveen, 2000; Chohan et al 2001), and these molecules exhibit potent antioxidant and DNAprotecting properties (Li & Liu, 2011). The coordination of a variety of metal centers to produce new complexes of ferrocene-derived Schiff base ligands has been studied for their interesting antibacterial activities compared to the free ligands (Chohan & Praveen, 2000). In a continuation of our research towards the synthesis of ferrocene-derived Schiff bases, we have been using 4-ferrocenyl aniline as an intermediate in the synthesis of new heterocyclic systems and have studied the condensation reactions between 4-ferrocenyl aniline and 4-chlorobenzaldehyde. The title compound (I) was obtained and characterized by single crystal X-ray diffraction techniques as well as by Hirshfeld surface analysis
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