The cocrystal rac‐1‐[(N, 4‐dimethylbenzenesulfonamido)methyl]‐2‐(diphenylphosphoryl)ferrocene–rac‐1‐[(N, 4‐dimethylbenzenesulfonamido)methyl]‐2‐(diphenylphosphanyl)ferrocene (0.45/0.55). Issue 3 (22nd February 2014)

• Record Type: Journal Article
• Authors: Wei, Muh‐Mei; Audin, Catherine; Manoury, Eric; Deydier, Eric; Daran, Jean‐Claude
• Is Part Of: Acta crystallographica. Volume 70:Issue 3(2014:Mar.)
• Page Start: 281
• Page End: 284
• Publication Date: 2014-02-22
• Subjects: Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229614002988
• Languages: English
• ISSNs: 2053-2296

Abstract

<abstract abstract-type="main" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p>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 <italic>rac</italic>‐1‐[(<italic>N</italic>, 4‐dimethylbenzenesulfonamido)methyl]‐2‐(diphenylphosphanyl)ferrocene, the title compound, [Fe(C<sub>5</sub>H<sub>5</sub>)(C<sub>26</sub>H<sub>25</sub>NO<sub>2</sub>PS)]<sub>0.55</sub>·[Fe(C<sub>5</sub>H<sub>5</sub>)(C<sub>26</sub>H<sub>25</sub>NO<sub>3</sub>PS)]<sub>0.45</sub>, was obtained as a by‐product. It is composed of a ferrocene group disubstituted by a partially oxidized diphenylphosphanyl group, as confirmed by <sup>31</sup>P NMR analysis, and an (<italic>N</italic>, 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 <italic>R</italic><sub>2</sub><sup>2</sup>(10) hydrogen‐bonding motifs, which build up a chain along the <italic>c</italic> axis.</p> </abstract>