2,2′-Bis(ferrocenylmethyl)-5,5′-(m-phenyl­ene)di-2H-tetra­zole

Fang Chen

doi:10.1107/S1600536809022442

. 2009 Jun 17;65(Pt 7):m788. doi: 10.1107/S1600536809022442

2,2′-Bis(ferrocenylmethyl)-5,5′-(m-phenylene)di-2H-tetrazole

Fang Chen ^a,^*

PMCID: PMC2969445 PMID: 21582716

Abstract

In the title compound, [Fe₂(C₅H₅)₂(C₂₀H₁₆N₈)], one of the unsubstituted cyclopentadiene (Cp) rings is disordered over two positions, with site-occupancy factors of 0.609 (19) and 0.391 (19). The dihedral angle formed by the benzene ring with the tetrazole rings are 51.86 (15) and 3.76 (11)°. In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular C—H⋯N hydrogen-bonding interactions.

Related literature

For the applications of ferrocene derivatives, see: Yang et al. (2002 ▶); Togni & Hayashi (1995 ▶); Long (1995 ▶); Roberto et al. (2000 ▶). For the crystal structures of related compounds, see: Hess et al. (1999 ▶); Base et al. (2002 ▶); Cao & Ye (2008 ▶).

Experimental

Crystal data

[Fe₂(C₅H₅)₂(C₂₀H₁₆N₈)]
M _r = 610.29
Triclinic,
a = 10.9665 (3) Å
b = 11.0860 (2) Å
c = 12.9410 (3) Å
α = 74.982 (4)°
β = 67.793 (4)°
γ = 70.738 (5)°
V = 1358.69 (8) Å³
Z = 2
Mo Kα radiation
μ = 1.10 mm⁻¹
T = 293 K
0.25 × 0.15 × 0.10 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: none
13984 measured reflections
6158 independent reflections
3375 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.117
S = 0.95
6158 reflections
407 parameters
621 restraints
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022442/rz2333sup1.cif

e-65-0m788-sup1.cif^{(29.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022442/rz2333Isup2.hkl

e-65-0m788-Isup2.hkl^{(301.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20B⋯N2ⁱ	0.97	2.49	3.391 (5)	154

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by a start-up grant from Southeast University.

supplementary crystallographic information

Comment

The chemistry of ferrocene has received much attention because of its applications in many fields, such as catalysis (Yang et al., 2002), organic or organometallic synthesis and materials (Togni & Hayashi, 1995), and non-linear optical (NLO) materials (Long, 1995; Roberto et al., 2000). As part of our continuing studies on new ferrocene compounds, the crystal structure of the title compound is reported herein.

In the title compound (Fig. 1), one of the unsubstituted cyclopentadiene (Cp) rings is disordered over two positions, with site-occupancy factors of 0.609 (19) and 0.391 (19) for the major and minor components, respectively. The dihedral angles formed within the (Cp)₂Fe unit by the disordered components with the substituted Cp ring are 1.1 (4) and 1.7 (6)°. The benzene ring forms dihedral angles of 3.76 (11) and 51.86 (15)° with the N1–N4/C7 and N5–N8/C19 tetrazole rings, respectively. The Fe—C distances range from 2.00 (2) to 2.06 (3) Å, and are in agreement with those reported for related compounds (Hess et al., 1999; Base et al., 2002). In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular C—H···N hydrogen bonding interactions (Table 1).

Experimental

To a mixture of [Fe(C₅H₅)(C₅H₄)N⁺(CH₃)₃I^-] (10 mmol) in H₂O (50 ml) was added 5-(3-(2H-tetrazol-5-yl)phenyl)-2H-tetrazole (5 mmol) and the mixture was heated to reflux temperature for 5 h. Then, the formed yellow precipitate was filtered. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a dichloromethane solution at room temperature after 3 days.