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Volume 65 
Part 3 
Page m264  
March 2009  

Received 23 January 2009
Accepted 5 February 2009
Online 11 February 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.011 Å
R = 0.098
wR = 0.199
Data-to-parameter ratio = 14.9
Details
Open access

rac-N,N'-Bis(1-ferrocenylethyl)pyridine-2,6-dicarboxamide

aDepartment of Applied Chemistry, College of Engineering, Kyungpook National University, Daegu 702-701, South Korea, and bCentral Instrument Facility, Gyeongsang National University, Jinju, South Korea
Correspondence e-mail: tjkim@knu.ac.kr

The title compound, [Fe2(C5H5)2(C21H21N3O2)], a potential novel N,N',N''-tridentate ligand with (non-crystallographic) C2 axial symmetry, adopts a U-shaped molecular conformation.

Related literature

For the applications of ferrocenes, see: Feng et al. (2008[Feng, Z., Yu, S. & Shang, Y. (2008). Appl. Org. Chem. 22, 577-582.]). For the use of 1,2-disubstituted planar-chiral ferrocenes in asymmetric catalysis, see: Richards & Locke (1998[Richards, C. J. & Locke, A. J. (1998). Tetrahedron Asymmetry, 9, 2377-2407.]); Kagan & Riant (1997[Kagan, H. B. & Riant, O. (1997). In Advances in Asymmetric Synthesis, edited by A. Hassner, Vol. 2, p 189. Greenwich, CT: JAI Press Inc.]). For the use of chiral C2-symmetric bisferrocenylaminophosphine ligands in asymmetric catalysis, see: Cho et al. (1999[Cho, D.-J., Jeon, S.-J., Kim, H.-S., Cho, C. S., Shim, S. C. & Kim, T.-J. (1999). Tetrahedron Asymmetry, 10, 3833-3848.]); Song et al. (1999[Song, J.-H., Cho, D.-J., Jeon, S.-J., Kim, Y.-H. & Kim, T.-J. (1999). Inorg. Chem. 38, 893-896.]). [alpha]-Diimine ligands are known to stablize organometallic complexes (van Koten & Vrieze, 1982[Koten, G. van & Vrieze, K. (1982). Adv. Organomet. Chem. 21, 151-239.]) and have been widely employed in a number of catalytic reactions, see: Fache et al. (2000[Fache, F., Schulz, E., Tommasino, M. L. & Lemaire, M. (2000). Chem. Rev. 100, 2159-2231.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe2(C5H5)2(C21H21N3O2)]

  • Mr = 589.29

  • Monoclinic, P 21 /n

  • a = 13.1787 (8) Å

  • b = 10.2961 (6) Å

  • c = 19.8474 (12) Å

  • [beta] = 103.620 (1)°

  • V = 2617.3 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.14 mm-1

  • T = 298 (2) K

  • 0.41 × 0.19 × 0.15 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.734, Tmax = 0.842

  • 14428 measured reflections

  • 5126 independent reflections

  • 3874 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.098

  • wR(F2) = 0.199

  • S = 1.20

  • 5126 reflections

  • 343 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.75 e Å-3

  • [Delta][rho]min = -0.61 e Å-3

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: WinGX Publication routines (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2359 ).


Acknowledgements

The work was supported by MKE through the Regional Technology Innovation Program (grant No. RTI 04-01-01). We thank Professor Lee Shimsung of Gyeongsang National University for providing instrumental facilities.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cho, D.-J., Jeon, S.-J., Kim, H.-S., Cho, C. S., Shim, S. C. & Kim, T.-J. (1999). Tetrahedron Asymmetry, 10, 3833-3848.  [ISI] [CrossRef] [ChemPort]
Fache, F., Schulz, E., Tommasino, M. L. & Lemaire, M. (2000). Chem. Rev. 100, 2159-2231.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Feng, Z., Yu, S. & Shang, Y. (2008). Appl. Org. Chem. 22, 577-582.  [CSD] [CrossRef] [ChemPort]
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Kagan, H. B. & Riant, O. (1997). In Advances in Asymmetric Synthesis, edited by A. Hassner, Vol. 2, p 189. Greenwich, CT: JAI Press Inc.
Koten, G. van & Vrieze, K. (1982). Adv. Organomet. Chem. 21, 151-239.  [CrossRef]
Richards, C. J. & Locke, A. J. (1998). Tetrahedron Asymmetry, 9, 2377-2407.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Song, J.-H., Cho, D.-J., Jeon, S.-J., Kim, Y.-H. & Kim, T.-J. (1999). Inorg. Chem. 38, 893-896.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2009). E65, m264  [ doi:10.1107/S160053680900422X ]

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