Crystal structure and Hirshfeld surface analysis study of (E)-1-(4-chlorophenyl)-N-(4-ferrocenylphenyl)methanimine

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Sghyar R., Moussaoui O., Sebbar N. K., Elmachkouri Y. A., Irrou E., HÖKELEK T., ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.77, pp.875-886, 2021 (ESCI, Scopus)

  • Publication Type: Article / Article
  • Volume: 77
  • Publication Date: 2021
  • Doi Number: 10.1107/s2056989021008033
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.875-886
  • Keywords: crystal structure, ferrocenyl, imine, C-H center dot center dot center dot pi(ring) interaction, FERROCENYL SCHIFF-BASE, INTERMOLECULAR INTERACTIONS, QUANTITATIVE-ANALYSIS, DERIVATIVES, ANTIOXIDANT, COMPLEXES, DNA
  • Open Archive Collection: AVESIS Open Access Collection
  • Hacettepe University Affiliated: Yes

Abstract

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)degrees, respectively. The unsubstituted cyclopentadienyl 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 molecules 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 center dot center dot center dot pi(ring) interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H center dot center dot center dot H (46.1%), H center dot center dot center dot C/C center dot center dot center dot H (35.4%) and H center dot center dot center dot Cl/Cl center dot center dot center dot H (13.8%) interactions. Thus C-H center dot center dot center dot pi(ring) and van der Waals interactions are the dominant interactions in the crystal packing.