Ferrocenylbutadiyne

Victor N Nemykin,Roman I Subbotin,Jason D Dorweiler

doi:10.1107/s1600536809005522

Ferrocenylbutadiyne

Victor N Nemykin, Roman I Subbotin + Show 1 more

Open Access

https://doi.org/10.1107/s1600536809005522

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Abstract

The title compound, [Fe(C5H5)(C9H5)], crystallizes in a form of a π–π-stacked assembly formed as a result of strong intermolecular π–π interactions between (a) the triple bonds of two neighboring butadiyne substituents overlapping in a ‘head-to-tail’ fashion [characterized by C⋯C short contacts of 3.622 (5), 3.567 (6) and 3.556 (6) Å] and (b) the triple bonds of the butadiyne substituent and substituted cyclopendadiene ring of neighboring molecules [C⋯C = 3.474 (5) and 3.492 (6) Å]. The linear butadiyne substituent has alternating C—C triple and single bonds, while the unsubstituted cyclopentadiene ring is slightly positionally disordered (although the structure reported here was solved as non-disordered) and retains a close to eclipsed conformation.

Highlights

The title compound, [Fe(C5H5)(C9H5)], crystallizes in a form of a –-stacked assembly formed as a result of strong intermolecular – interactions between (a) the triple bonds of two neighboring butadiyne substituents overlapping in a ‘head-to-tail’ fashion [characterized by CÁ Á ÁC short contacts of 3.622 (5), 3.567 (6) and 3.556 (6) A ] and (b) the triple bonds of the butadiyne substituent and substituted cyclopendadiene ring of neighboring molecules [CÁ Á ÁC = 3.474 (5) and 3.492 (6) A ]
The X-ray data were collected at the University of Minnesota Duluth X-ray crystallography facility
Comment Ferrocene derivatives have been useful as antitumor agents (Fouda et al, 2007) and as electron transfer molecules. (Stepnika, 2008; Nemykin et al, 2001, 2007a, 2007b, 2007c, 2008; Osakada et al, 2006) The title compound represents a precursor for the preparation of butadiyne like dinuclear ferrocene molecules. (Bruce et al, 2004, Yuan et al, 1993)

Summary

Introduction

For the synthesis of the title compound, see: Yuan et al (1993); Nemykin et al (2007c). Rigaku AFC-7R diffractometer Absorption correction: scan (North et al, 1968) Tmin = 0.58, Tmax = 0.70 2549 measured reflections 2411 independent reflections

Results

Conclusion