title: The cocrystal rac-1-[(N,4-dimethylbenzenesulfonamido)methyl]-2-(diphenylphosphoryl)ferrocene-rac-1-[(N,4-dimethylbenzenesulfonamido)methyl]-2-(diphenylphosphanyl)ferrocene (0.45/0.55).
abstract: As part of our interest in the synthesis and catalytic applications of chiral (diphenylphosphanyl)ferrocene ligands, we designed a number of P,N-containing ligands for use in asymmetric transfer hydrogenation (ATH). During the synthetic procedure to obtain rac-1-[(N,4-dimethylbenzenesulfonamido)methyl]-2-(diphenylphosphanyl)ferrocene, the title compound, [Fe(C5H5)(C26H25NO2PS)]0.55 · [Fe(C5H5)(C26H25NO3PS)]0.45, was obtained as a by-product. It is composed of a ferrocene group disubstituted by a partially oxidized diphenylphosphanyl group, as confirmed by (31)P NMR analysis, and an (N,4-dimethylbenzenesulfonamido)methyl substituent. Owing to the partially oxidized diphenylphosphanyl group, it is best to view the crystal as being composed of a mixture of non-oxidized and oxidized phosphane, so it can be regarded as a cocrystal. It is also a racemate. To the best of our knowledge, the P=O distance [1.344 (4) Å] is the shortest observed for related (diphenylphosphoryl)ferrocene compounds. The packing is stabilized by weak C-H...O interactions, forming R2(2)(10) hydrogen-bonding motifs, which build up a chain along the c axis.
authors.affiliation: Laboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France.
authors.forename: Muh Mei
authors.initials: MM
authors.lastname: Wei
authors.affiliation: Laboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France.
authors.forename: Catherine
authors.initials: C
authors.lastname: Audin
authors.affiliation: Laboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France.
authors.forename: Eric
authors.initials: E
authors.lastname: Manoury
authors.affiliation: Laboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France.
authors.forename: Eric
authors.initials: E
authors.lastname: Deydier
authors.affiliation: Laboratoire de Chimie de Coordination, 205 route de Narbonne, 31077 Toulouse Cedex 04, France.
authors.forename: Jean Claude
authors.initials: JC
authors.lastname: Daran
mesh_terms: D056831:Coordination Complexes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005296:Ferrous Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D008024:Ligands; D000075163:Metallocenes; D015394:Molecular Structure
chemical_list: D056831:Coordination Complexes; D005296:Ferrous Compounds; D008024:Ligands; D000075163:Metallocenes; C004998:ferrocene
keywords: asymmetric transfer hydrogenation (ATH); crystal structure; diphenylphosphanyl oxidation; short P=O bond