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

Reddy, P.A.N.; Nasiruzzaman, S.M.; Lee, J.E.; Kim, T.-J.

doi:10.1107/S160053680900422X

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 (C-C) = 0.011 Å
R = 0.098
wR = 0.199
Data-to-parameter ratio = 14.9
Details

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

Pattubala A. N. Reddy,^a Sk. Md Nasiruzzaman,^a Ji Eun Lee ^b and Tae-Jeong Kim ^a ^*

^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). For the use of 1,2-disubstituted planar-chiral ferrocenes in asymmetric catalysis, see: Richards & Locke (1998); Kagan & Riant (1997). For the use of chiral C2-symmetric bisferrocenylaminophosphine ligands in asymmetric catalysis, see: Cho et al. (1999); Song et al. (1999). [alpha] -Diimine ligands are known to stablize organometallic complexes (van Koten & Vrieze, 1982) and have been widely employed in a number of catalytic reactions, see: Fache et al. (2000).

Experimental

Crystal data

[Fe₂(C₅H₅)₂(C₂₁H₂₁N₃O₂)]
M_r = 589.29
Monoclinic, P 2₁ /n
a = 13.1787 (8) Å
b = 10.2961 (6) Å
c = 19.8474 (12) Å
= 103.620 (1)°
V = 2617.3 (3) Å³
Z = 4
Mo K radiation
= 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; Sheldrick, 2004) T_min = 0.734, T_max = 0.842
14428 measured reflections
5126 independent reflections
3874 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.098
wR(F²) = 0.199
S = 1.20
5126 reflections
343 parameters
H-atom parameters constrained
_max = 0.75 e Å^-3
_min = -0.61 e Å^-3

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: WinGX Publication routines (Farrugia, 1999).

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.
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.
Fache, F., Schulz, E., Tommasino, M. L. & Lemaire, M. (2000). Chem. Rev. 100, 2159-2231.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Feng, Z., Yu, S. & Shang, Y. (2008). Appl. Org. Chem. 22, 577-582.
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.
Richards, C. J. & Locke, A. J. (1998). Tetrahedron Asymmetry, 9, 2377-2407.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Song, J.-H., Cho, D.-J., Jeon, S.-J., Kim, Y.-H. & Kim, T.-J. (1999). Inorg. Chem. 38, 893-896.

metal-organic compounds