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Volume 67 
Part 8 
Page m1113  
August 2011  

Received 29 June 2011
Accepted 3 July 2011
Online 23 July 2011

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.034
wR = 0.097
Data-to-parameter ratio = 17.7
Details
Open access

N-(Quinolin-8-yl)ferrocene-1-carboxamide

Xia Lia* and Ling-Zhi Dua

aDepartment of Chemistry and Chemical Engineering, Henan University of Urban Construction, Pingdingshan, Henan 467044, People's Republic of China
Correspondence e-mail: lixia@hncj.edu.cn

In the title compound, [Fe(C5H5)(C15H11N2O)], the cyclopentadienyl rings are essentially eclipsed, and the dihedral angle between the cyclopentadienyl ring planes is 0.632 (10)°. The Fe atom is slightly closer to the substituted cyclopentadienyl ring, with an Fe-centroid distance of 1.6374 (3) Å [1.6494 (3) Å for the unsubstituted ring]. The amide group is essentially coplanar with the substituted cyclopentadienyl ring, with an N-C(O)-C-C torsion angle of 2.3 (3)°.

Related literature

For background to the chemical, stereochemical and electrochemical properties of ferrocene, see: Togni & Hayashi (1995[Togni, A. & Hayashi, T. (1995). In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science. New York: VCH Publishers.]). Ferrocene has been extensively incorporated into larger compounds in order to take advantage of these properties, see: Abd-El-Aziz & Manners (2007[Abd-El-Aziz, A. S. & Manners, I. (2007). In Frontiers in Transition Metal-Containing Polymers. Hoboken, NJ: Wiley.]); Fang et al. (2001[Fang, C. J., Duan, C. Y., Guo, D., He, C., Meng, Q. J., Wang, Z. M. & Yan, C. H. (2001). Chem. Commun. pp. 2540-2541.]); Mata et al. (2001[Mata, J. A., Peris, E., Asselberghs, I., Van Boxel, R. & Persoons, A. (2001). New J. Chem. 25, 1043-1046.]). For our research on ferrocenyl derivatives and their metal complexes, see: Li et al. (2008[Li, X., Liu, W., Zhang, H. Y. & Wu, B. L. (2008). J. Organomet. Chem. 693, 3295-3302.], 2009[Li, X., Wu, B. L., Liu, W., Niu, C. Y., Niu, Y. Y. & Zhang, H. Y. (2009). J. Coord. Chem. 62, 3142-3156.]).

[Scheme 1]

Experimental

Crystal data

  • [Fe(C5H5)(C15H11N2O)]

  • Mr = 356.20

  • Orthorhombic, P b c a

  • a = 10.1680 (17) Å

  • b = 12.133 (2) Å

  • c = 26.079 (4) Å

  • V = 3217.4 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.95 mm-1

  • T = 296 K

  • 0.46 × 0.37 × 0.25 mm
Data collection

  • Rigaku Mercury CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2000[Rigaku (2000). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.668, Tmax = 0.795

  • 18658 measured reflections

  • 3940 independent reflections

  • 2996 reflections with I > 2[sigma](I)

  • Rint = 0.031
Refinement

  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.097

  • S = 1.01

  • 3940 reflections

  • 222 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Data collection: CrystalClear (Rigaku, 2000[Rigaku (2000). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2441 ).

Acknowledgements

We gratefully acknowledge financial support from the Foundation of Henan Educational Committee (2011B150001) and the Foundation of Henan University of Urban Construction (2010JYB007).

References

Abd-El-Aziz, A. S. & Manners, I. (2007). In Frontiers in Transition Metal-Containing Polymers. Hoboken, NJ: Wiley.
Fang, C. J., Duan, C. Y., Guo, D., He, C., Meng, Q. J., Wang, Z. M. & Yan, C. H. (2001). Chem. Commun. pp. 2540-2541.
Li, X., Liu, W., Zhang, H. Y. & Wu, B. L. (2008). J. Organomet. Chem. 693, 3295-3302.  [CrossRef] [ChemPort]
Li, X., Wu, B. L., Liu, W., Niu, C. Y., Niu, Y. Y. & Zhang, H. Y. (2009). J. Coord. Chem. 62, 3142-3156.  [CrossRef] [ChemPort]
Mata, J. A., Peris, E., Asselberghs, I., Van Boxel, R. & Persoons, A. (2001). New J. Chem. 25, 1043-1046.  [CrossRef] [ChemPort]
Rigaku (2000). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Togni, A. & Hayashi, T. (1995). In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science. New York: VCH Publishers.

Acta Cryst (2011). E67, m1113  [ doi:10.1107/S1600536811026341 ]

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