Synthesis and crystal structure of [(Sp )-(2-phenyl-ferrocen-yl)meth-yl]tri-methyl-ammonium iodide di-chloro-methane monosolvate

Abdelhak Lachguar; Eric Deydier; Agnès Labande; Eric Manoury; Rinaldo Poli; Jean-Claude Daran

doi:10.1107/S2056989022006053

Synthesis and crystal structure of [(S_p )-(2-phenyl-ferrocen-yl)meth-yl]tri-methyl-ammonium iodide di-chloro-methane monosolvate

Acta Crystallogr E Crystallogr Commun. 2022 Jun 14;78(Pt 7):722-726. doi: 10.1107/S2056989022006053. eCollection 2022 Jul 1.

Authors

Abdelhak Lachguar^{1

2}, Eric Deydier^{1

2}, Agnès Labande¹, Eric Manoury¹, Rinaldo Poli¹, Jean-Claude Daran¹

Affiliations

¹ CNRS, LCC (Laboratoire de Chimie de Coordination), Université de Toulouse, UPS, INPT, 205 Route de Narbonne, F-31077 Toulouse Cedex 4, France.
² IUT A Paul Sabatier, de Chimie, Avenue Georges Pompidou, CS 20258, F-81104, Castres Cedex, France.

Abstract

As a follow-up to our research on the chemistry of disubstituted ferrocene derivatives, the synthesis and the structure of the title compound, [Fe(C₅H₅)(C₁₅H₁₉N)]I·CH₂Cl₂, is described. The cation mol-ecule is built up from a ferrocene disubstituted by a tri-methyl-ammonium methyl group and a phenyl ring. The asymmetric unit contains the iodide to equilibrate the charge and a disordered di-chloro-methane solvate. The disordered model results from a roughly statistical exchange (0.6/0.4) between one Cl and one H. The packing of the structure is stabilized by weak C-H⋯X (X = I, Cl), C-H⋯π(Cp) and C-Cl⋯π(phen-yl) inter-actions, building a three-dimensional network. The cation has planar chirality with S_p (Fc) absolute configuration. The structure of the title compound is compared with related disubstituted (tri-meth-ylammonio)-methyl ferrocenes.

Keywords: 1,2-disubstitued ferrocene; asymetric catalysis; chiral ligands; crystal structure; disordered dichloromethane; planar chirality.

Grants and funding

Funding for this research was provided by: Centre National de la Recherche Scientifique (CNRS), Midi-Pyrénnées region, Institut Universitaire de Technologie (IUT) Paul Sabatier and the Syndicat Mixte de Castres Mazamet (PhD grant ALDOCT000431.