Monohalogenated ferrocenes C<inf>5</inf>H<inf>5</inf>FeC<inf>5</inf>H <inf>4</inf> X (X = Cl, Br and I) and a second polymorph of C <inf>5</inf>FeC<inf>5</inf>H<inf>4</inf>I

A.S. Romanov, J.M. Mulroy, V.N. Khrustalev, M.Y. Antipin, T.V. Timofeeva

Research output: Contribution to journalArticlepeer-review

Abstract

The structures of the three title monosubstituted ferrocenes, namely 1-chloro­ferrocene, [Fe(C5H5)(C5H4Cl)], (I), 1-bromo­ferrocene, [Fe(C5H5)(C5H4Br)], (II), and 1-iodo­ferrocene, [Fe(C5H5)(C5H4I)], (III), were determined at 100 K. The chloro- and bromo­ferrocenes are isomorphous crystals. The new triclinic polymorph [space group P\overline{1}, Z = 4, T = 100 K, V = 943.8 (4) Å3] of iodo­ferrocene, (III), and the previously reported monoclinic polymorph of (III) [Laus, Wurst & Schottenberger (2005). Z. Kristallogr. New Cryst. Struct. 220, 229-230; space group Pc, Z = 4, T = 100 K, V = 924.9 Å3] were obtained by crystallization from ethanolic solutions at 253 and 303 K, respectively. All four phases contain two independent mol­ecules in the unit cell. The relative orientations of the cyclo­penta­dienyl (Cp) rings are eclipsed and staggered in the independent mol­ecules of (I) and (II), while (III) demonstrates only an eclipsed conformation. The triclinic and monoclinic polymorphs of (III) contain nonbonded inter­molecular I...I contacts, causing different packing modes. In the triclinic form of (III), the mol­ecules are arranged in zigzag tetra­mers, while in the monoclinic form the mol­ecules are arranged in zigzag chains along the a axis. Crystallographic data for (III), along with the computed lattice energies of the two polymorphs, suggest that the monoclinic form is more stable.
Original languageEnglish
Pages (from-to)M426-M430
Number of pages5
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume65
Issue number11
DOIs
Publication statusPublished - 2009

Keywords

  • Crystallization
  • Ferrous compounds
  • Halogens
  • Models, molecular

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