Acta Crystallographica Section C

Volume 65, Part 11 (November 2009)

metal-organic compounds

 

Monohalogenated ferrocenes C₅H₅FeC₅H₄X (X = Cl, Br and I) and a second polymorph of C₅H₅FeC₅H₄I

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

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, 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 II 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.

Formula: [Fe(C₅H₅)(C₅H₄Cl)], [Fe(C₅H₅)(C₅H₄Br)] and [Fe(C₅H₅)(C₅H₄I)]

	Structure factor file (CIF format) (225.2 kbytes) [ doi:10.1107/S0108270109034763/sf3110Isup2.hkl ] Contains datablock I
	Structure factor file (CIF format) (220.7 kbytes) [ doi:10.1107/S0108270109034763/sf3110IIsup3.hkl ] Contains datablock II
	Structure factor file (CIF format) (194.7 kbytes) [ doi:10.1107/S0108270109034763/sf3110IVsup5.hkl ] Contains datablock IV
	Structure factor file (CIF format) (229.0 kbytes) [ doi:10.1107/S0108270109034763/sf3110IIIsup4.hkl ] Contains datablock III

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