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Volume 68 
Part 12 
Page m1535  
December 2012  

Received 2 November 2012
Accepted 21 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.022
wR = 0.061
Data-to-parameter ratio = 17.7
Details
Open access

(4-{[(Pyridin-4-yl)methylidene]amino}phenyl)ferrocene

aSchool of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
Correspondence e-mail: owaga@ukzn.ac.za

The asymetric unit of the title compound, [Fe(C5H5)(C17H13N2)], contains two independent molecules whose conformations differ, especially in the 4-{(pyridin-4-yl)methylidene]amino}phenyl unit where one is flipped by almost 180°. The cyclopentadienyl rings of the ferrocene unit also exhibit different staggered conformations: in one molecule the conformation is staggered by 9.43 (2)° and in the other by 24.46 (1)° from an ideal eclipsed geometry. The plane of the benzene ring is tilted away from the ferrocene group in both molecules, with dihedral angles of 6.97 (1) and 10.30 (2)°. The benzene ring is also slightly twisted from the plane of the pyridine ring, with dihedral angles of 5.98 (2) and 6.51 (2)° in the two molecules.

Related literature

For related compounds, see: Nyamori et al. (2012[Nyamori, V. O., Zulu, S. M. & Omondi, B. (2012). Acta Cryst. E68, m353.]); Nyamori & Moodley (2011[Nyamori, V. O. & Moodley, N. N. (2011). Acta Cryst. E67, m1293.]). For the synthesis, see: Rajput et al. (2006[Rajput, J., Hutton, A. T., Moss, J. R., Su, H. & Imrie, C. (2006). J. Organomet. Chem. 691, 4573-4588.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C17H13N2)]

  • Mr = 366.23

  • Monoclinic, P 21

  • a = 10.7200 (3) Å

  • b = 7.4015 (2) Å

  • c = 20.8517 (6) Å

  • [beta] = 93.044 (1)°

  • V = 1652.12 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.92 mm-1

  • T = 173 K

  • 0.56 × 0.45 × 0.10 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.627, Tmax = 0.914

  • 36615 measured reflections

  • 7976 independent reflections

  • 7617 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.022

  • wR(F2) = 0.061

  • S = 1.02

  • 7976 reflections

  • 451 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3568 Friedel pairs

  • Flack parameter: 0.003 (8)

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5267 ).


Acknowledgements

The authors thank the University of KwaZulu-Natal and IBSA for financial support.

References

Bruker (2008). APEX2, SAINT-Plus, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Nyamori, V. O. & Moodley, N. N. (2011). Acta Cryst. E67, m1293.  [CSD] [CrossRef] [details]
Nyamori, V. O., Zulu, S. M. & Omondi, B. (2012). Acta Cryst. E68, m353.  [CSD] [CrossRef] [details]
Rajput, J., Hutton, A. T., Moss, J. R., Su, H. & Imrie, C. (2006). J. Organomet. Chem. 691, 4573-4588.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, m1535  [ doi:10.1107/S1600536812047812 ]

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