Dichlorido(η6-p-cymene)(4-fluoro­aniline-κN)ruthenium(II)

Sykora, R.E.; Harris, A.G.; Clements, J.W.; Hoffman, N.W.

doi:10.1107/S1600536810051962

Volume 67
Part 1
Pages m99-m100
January 2011

Received 1 December 2010
Accepted 11 December 2010
Online 18 December 2010

Key indicators
Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.007 Å
R = 0.034
wR = 0.090
Data-to-parameter ratio = 15.7
Details

Dichlorido(⁶-p-cymene)(4-fluoroaniline-N)ruthenium(II)

Richard E. Sykora,^a Andrew G. Harris,^a Jason W. Clements ^a and Norris W. Hoffman ^a ^*

^aDepartment of Chemistry, University of South Alabama, Mobile, AL 36688-0002, USA
Correspondence e-mail: nhoffman@jaguar1.usouthal.edu

The title compound, [RuCl₂(C₁₀H₁₄)(C₆H₆FN)], a pseudo-octahedral d⁶ complex, has the expected piano-stool geometry around the Ru(II) atom. The fluoroaniline ring forms a dihedral angle of 19.3 (2)° with the p-cymene ring. In the crystal, two molecules form an inversion dimer via a pair of N-HCl hydrogen bonds. Weak intermolecular C-HCl interactions involving the p-cymene ring consolidate the crystal packing.

Related literature

For applications of ( [eta] ⁶-p-cymene)Ru(II) dihalides in organic synthesis, see: Boutadla et al. (2010). For studies of ( [eta] ⁶-arene)Ru(II) dihalides in bioinorganic chemistry, see: den Heeten et al. (2010). For anti-tumor medical applications of ( [eta] ⁶-arene)Ru(II) systems, see: Hanif et al. (2010). For conversion of [( [eta] ⁶-p-cymene)RuCl₂]₂ with two molar equivalents of neutral unidentate nitrogen ligands into monomeric pseudo-octahedral piano-stool complexes of general formula ( [eta] ⁶-p-cymene)Ru(N-ligand)Cl₂, see: Burrell & Steedman (1997); Govindaswamy & Kollipara (2006); Begley et al. (1991). For crystal structures of Ni-triad complexes of 4-fluoroaniline, see: Randell et al. (2006); Fawcett et al. (2005); Padmanabhan et al. (1985). For applications of ¹⁹F-NMR reporter moieties in monitoring ligand-substitution equilibria, see: Hoffman et al. (2009); Carter et al. (2004).

Experimental

Crystal data

[RuCl₂(C₁₀H₁₄)(C₆H₆FN)]
M_r = 417.30
Monoclinic, P 2₁ /n
a = 8.6492 (9) Å
b = 12.2458 (13) Å
c = 15.6471 (16) Å
= 93.271 (8)°
V = 1654.6 (3) Å³
Z = 4
Mo K radiation
= 1.27 mm^-1
T = 290 K
0.26 × 0.25 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.635, T_max = 0.779
3234 measured reflections
3027 independent reflections
2284 reflections with I > 2(I)
R_int = 0.048
3 standard reflections every 120 min intensity decay: none

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.090
S = 1.00
3027 reflections
193 parameters
H-atom parameters constrained
_max = 0.57 e Å^-3
_min = -0.67 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1BCl2ⁱ	0.90	2.39	3.225 (3)	154
C6-H6Cl1ⁱⁱ	0.93	2.72	3.384 (4)	129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CAD-4-PC (Enraf-Nonius, 1993); cell refinement: CAD-4-PC; data reduction: XCAD-4PC (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2638 ).

Acknowledgements

The authors gratefully acknowledge the Department of Chemistry and the Univeristy Committee for Undergraduate Research at USA for their generous support and the Department of Energy and Oak Ridge National Laboratory for the diffractometer used in this study.

References

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