Crystal structure and Hirshfeld surface analysis study of (E)-1-(4-chloro-phen-yl)- N-(4-ferrocenylphen-yl)methanimine

Riham Sghyar; Oussama Moussaoui; Nada Kheira Sebbar; Younesse Ait Elmachkouri; Ezaddine Irrou; Tuncer Hökelek; Joel T Mague; Abdesslam Bentama; El Mestafa El Hadrami

doi:10.1107/S2056989021008033

Crystal structure and Hirshfeld surface analysis study of (E)-1-(4-chloro-phen-yl)- N-(4-ferrocenylphen-yl)methanimine

Acta Crystallogr E Crystallogr Commun. 2021 Aug 10;77(Pt 9):875-879. doi: 10.1107/S2056989021008033. eCollection 2021 Sep 1.

Authors

Riham Sghyar¹, Oussama Moussaoui¹, Nada Kheira Sebbar², Younesse Ait Elmachkouri², Ezaddine Irrou², Tuncer Hökelek³, Joel T Mague⁴, Abdesslam Bentama¹, El Mestafa El Hadrami¹

Affiliations

¹ Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, Road Immouzer, BP 2202 Fez, Morocco.
² Applied Chemistry and Environment Laboratory, Applied Bioorganic Chemistry Team, Faculty of Science, Ibn Zohr University, Agadir, Morocco.
³ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey.
⁴ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.

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.

Keywords: C—H⋯π(ring) interaction; crystal structure; ferrocenyl; imine.

Grants and funding

This work was funded by Tulane University; Hacettepe University Scientific Research Project Unit grant 013 D04 602 004.