Crystal structure and Hirshfeld surface analysis of (Z)- N-{chloro-[(4-ferrocenylphen-yl)imino]-meth-yl}-4-ferrocenylaniline N, N-di-methyl-formamide monosolvate

Riham Sghyar; Abdeslem Bentama; Amal Haoudi; Ahmed Mazzah; Joel T Mague; Tuncer Hökelek; El Mestafa El Hadrami; Nada Kheira Sebbar

doi:10.1107/S2056989024001002

Crystal structure and Hirshfeld surface analysis of (Z)- N-{chloro-[(4-ferrocenylphen-yl)imino]-meth-yl}-4-ferrocenylaniline N, N-di-methyl-formamide monosolvate

Acta Crystallogr E Crystallogr Commun. 2024 Feb 2;80(Pt 3):262-266. doi: 10.1107/S2056989024001002. eCollection 2024 Mar 1.

Authors

Riham Sghyar¹, Abdeslem Bentama¹, Amal Haoudi¹, Ahmed Mazzah², Joel T Mague³, Tuncer Hökelek⁴, El Mestafa El Hadrami¹, Nada Kheira Sebbar^{5

6}

Affiliations

¹ Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Science And Technology, Road Immouzer, BP 2202 Fez, Morocco.
² Science and Technology of Lille USR 3290, Villeneuve d'ascq cedex, France.
³ Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
⁴ Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Türkiye.
⁵ Laboratory of Organic and Physical Chemistry, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibnou Zohr University, Agadir, Morocco.
⁶ Laboratory of Plant Chemistry, Organic and Bioorganic Synthesis, Faculty of Sciences, Mohammed V University in Rabat, 4 Avenue Ibn Battouta BP 1014 RP, Rabat, Morocco.

Abstract

The title mol-ecule, [Fe₂(C₅H₅)₂(C₂₃H₁₇ClN₂)]·C₃H₇NO, is twisted end to end and the central N/C/N unit is disordered. In the crystal, several C-H⋯π(ring) inter-actions lead to the formation of layers, which are connected by further 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 (60.2%) and H⋯C/C⋯H (27.0%) inter-actions. Hydrogen bonding, C-H⋯π(ring) inter-actions and van der Waals inter-actions dominate the crystal packing.

Keywords: C—H⋯π(ring) interactions; carbamidic chloride; crystal structure; ferrocene; hydrogen bond.

Grants and funding

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory. TH is grateful to Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004).