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Volume 70 
Part 1 
Page m2  
January 2014  

Received 20 May 2013
Accepted 15 November 2013
Online 4 December 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.004 Å
R = 0.031
wR = 0.078
Data-to-parameter ratio = 14.1
Details
Open access

(6-Chloropyridazin-3-yl)ferrocene

aSchool of Chemical Engineering and Energy, Zhengzhou University, Henan, Zhengzhou, 450052, People's Republic of China,bSchool of Food and Bioengineering, Zhengzhou University of Light Industry, Henan, Zhengzhou, 450052, People's Republic of China, and cHenan Industrial University Chemical Technology Vocational College, Henan, Zhengzhou, 450052, People's Republic of China
Correspondence e-mail: zhaowenen@zzu.edu.cn

The asymmetric unit of the title compound, [Fe(C5H5)(C9H6ClN2)], contains two independent mol­ecules in which the cyclo­penta­dienyl rings are almost parallel, making dihedral angles of 2.16 (4) and 2.71 (5), and the dihedral angles between the pyridazinyl and substituted cyclo­penta­dienyl rings are 9.65 (5) and 11.53 (8)°. In the crystal, mol­ecules are linked by C-H...N hydrogen bonds into chains along the c-axis direction.

Related literature

For the synthesis of the title compound, see: Xu et al. (2012[Xu, C., Li, H. M., Wang, Z. Q., Fu, W. J., Zhang, Y. Q. & Ji, B. M. (2012). Aust. J. Chem. 65, 366-370.]). For applications of organomercury compounds, see: Beletskaya et al. (2001[Beletskaya, I. P., Tsvetkov, A. V., Latyshev, G. V., Tafeenko, V. A. & Lukashev, N. V. (2001). J. Organomet. Chem. 637-639, 653-663.]); Tsvetkov et al. (2000[Tsvetkov, A. V., Tsvetkov, A. V., Lukashev, N. V. & Beletskaya, I. P. (2000). Tetrahedron Lett. 41, 3987-3990.]); Xu et al. (2010[Xu, C., Zhang, Y. P., Wang, Z. Q., Fu, W. J., Hao, X. Q., Xu, Y. & Ji, B. M. (2010). Chem. Commun. 46, 6852-6854.]); For palladium-catalysed reactions, see: Meijere & Diederich (2004[Meijere, A. D. & Diederich, F. (2004). Metal-catalyzed Cross-coupling Reactions. 2nd ed. Weinheim: Wiley-VCH.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C9H6ClN2)]

  • Mr = 298.55

  • Monoclinic, C 2/c

  • a = 20.5488 (19) Å

  • b = 12.3788 (6) Å

  • c = 23.043 (2) Å

  • [beta] = 122.843 (13)°

  • V = 4924.5 (7) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 1.42 mm-1

  • T = 291 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Oxford Diffraction Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Abingdon, England.]) Tmin = 0.675, Tmax = 0.718

  • 18413 measured reflections

  • 4575 independent reflections

  • 3783 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.078

  • S = 1.04

  • 4575 reflections

  • 325 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...N3i 0.98 2.55 3.454 (4) 153
C12-H12...N4i 0.93 2.41 3.320 (4) 166
C26-H26...N2ii 0.93 2.43 3.302 (4) 156
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: RN2116 ).


References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Abingdon, England.
Beletskaya, I. P., Tsvetkov, A. V., Latyshev, G. V., Tafeenko, V. A. & Lukashev, N. V. (2001). J. Organomet. Chem. 637-639, 653-663.  [CSD] [CrossRef] [ChemPort]
Meijere, A. D. & Diederich, F. (2004). Metal-catalyzed Cross-coupling Reactions. 2nd ed. Weinheim: Wiley-VCH.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tsvetkov, A. V., Tsvetkov, A. V., Lukashev, N. V. & Beletskaya, I. P. (2000). Tetrahedron Lett. 41, 3987-3990.  [Web of Science] [CrossRef] [ChemPort]
Xu, C., Li, H. M., Wang, Z. Q., Fu, W. J., Zhang, Y. Q. & Ji, B. M. (2012). Aust. J. Chem. 65, 366-370.  [ChemPort]
Xu, C., Zhang, Y. P., Wang, Z. Q., Fu, W. J., Hao, X. Q., Xu, Y. & Ji, B. M. (2010). Chem. Commun. 46, 6852-6854.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2014). E70, m2  [ doi:10.1107/S1600536813031310 ]

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