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Volume 68 
Part 1 
Pages m35-m36  
January 2012  

Received 18 October 2011
Accepted 5 December 2011
Online 10 December 2011

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.025
wR = 0.068
Data-to-parameter ratio = 14.8
Details
Open access

Ethyl 3-ferrocenyl-1-(pyridin-2-ylmethyl)-1H-pyrazole-5-carboxylate

Ilia A. Guzei,a* Lara C. Spencer,a Apollinaire Munyanezab and James Darkwab

aDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706, USA, and bDepartment of Chemistry, University of Johannesburg, Auckland Park Kingsway Campus, Johannesburg 2006, South Africa
Correspondence e-mail: iguzei@chem.wisc.edu

The title compound, [Fe(C5H5)(C17H16N3O2)], crystallizes with an essentially eclipsed conformation of the cyclopentadienyl (Cp) rings. The unsubstituted ring is disordered over two positions with the major component being present 90 (1)% of the time. The substituted Cp ring, the pyrazole ring and three atoms of the ethoxycarbonyl group form a conjugated [pi]-system. These 13 atoms are coplanar within 0.09 Å.

Related literature

For the preparation of (pyrazol-1-ylmethyl)pyridine compounds, see: House et al. (1986[House, D. A., Steel, P. J. & Watson, A. A. (1986). Aust. J. Chem. 39, 1525-1536.]). For modification of the chemistry of metal (pyrazol-1-ylmethyl)pyridine compounds due to the substituents on the pyrazolyl ring, see: Ojwach et al. (2007[Ojwach, S. O., Guzei, I. A., Darkwa, J. & Mapolie, S. F. (2007). Polyhedron, 26, 851-861.], 2009[Ojwach, S. O., Guzei, I. A., Benade, L. L., Mapolie, S. F. & Darkwa, J. (2009). Organometallics, 28, 2127-2133.]). Typical structural parameters were confirmed by a Mogul geometry check, see: Bruno et al. (2002[Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.]). Fe(II)-centroid distances for related compounds were found in the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For discussion of the twinning of a nickel complex utilizing (3-ferrocenyl-5-ethylcarboxylate-pyrazolyl-1-yl-methyl)pyridine as a ligand, see: Guzei et al. (2012[Guzei, I. A., Herbst-Irmer, R., Munyaneza, A. & Darkwa, J. (2012). Inorg. Chem. Submitted.]).

[Scheme 1]

Experimental

Crystal data

  • [Fe(C5H5)(C17H16N3O2)]

  • Mr = 415.27

  • Triclinic, [P \overline 1]

  • a = 10.3913 (2) Å

  • b = 10.6343 (2) Å

  • c = 10.7371 (2) Å

  • [alpha] = 86.6909 (8)°

  • [beta] = 65.5907 (7)°

  • [gamma] = 63.8778 (7)°

  • V = 958.82 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.81 mm-1

  • T = 296 K

  • 0.35 × 0.28 × 0.21 mm
Data collection

  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: analytical (SADABS; Bruker, 2011)[Bruker (2011). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 0.765, Tmax = 0.851

  • 19702 measured reflections

  • 3852 independent reflections

  • 3672 reflections with I > 2[sigma](I)

  • Rint = 0.020
Refinement

  • R[F2 > 2[sigma](F2)] = 0.025

  • wR(F2) = 0.068

  • S = 1.05

  • 3852 reflections

  • 261 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2011[Bruker (2011). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL, OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]), FCF_filter (Guzei, 2007[Guzei, I. A. (2007). FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.]) and INSerter (Guzei, 2007[Guzei, I. A. (2007). FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.]); molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL, publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and modiCIFer (Guzei, 2007[Guzei, I. A. (2007). FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2331 ).

Acknowledgements

We are grateful for financial support for this work through a postdoctoral fellowship to AM by the National Research Foundation (NRF) and the NRF-DST Centre of Excellence in Catalysis (c*change).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2011). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389-397.  [ISI] [CrossRef] [details]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Guzei, I. A. (2007). FCF_filter, INSerter and modiCIFer. Molecular Structure Laboratory, University of Wisconsin-Madison, Madison, Wisconsin, USA.
Guzei, I. A., Herbst-Irmer, R., Munyaneza, A. & Darkwa, J. (2012). Inorg. Chem. Submitted.
House, D. A., Steel, P. J. & Watson, A. A. (1986). Aust. J. Chem. 39, 1525-1536.  [ChemPort]
Ojwach, S. O., Guzei, I. A., Benade, L. L., Mapolie, S. F. & Darkwa, J. (2009). Organometallics, 28, 2127-2133.  [CSD] [CrossRef] [ChemPort]
Ojwach, S. O., Guzei, I. A., Darkwa, J. & Mapolie, S. F. (2007). Polyhedron, 26, 851-861.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2012). E68, m35-m36   [ doi:10.1107/S160053681105238X ]

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