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Volume 69 
Part 9 
Page m486  
September 2013  

Received 5 August 2013
Accepted 6 August 2013
Online 10 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
Disorder in main residue
R = 0.060
wR = 0.122
Data-to-parameter ratio = 15.1
Details
Open access

2-(3-Chlorobenzoyl)-3-(3,4-dichlorophenyl)-1-(4-ferrocenylphenyl)guanidine

aDepartment of Chemistry, Gomal University, Dera Ismail Khan, K.P.K, Pakistan,bDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the title compound, [Fe(C5H5)(C25H17Cl3N3O)], the isolated cyclopentadienyl (Cp) ring is disordered over two set of sites in a 0.577 (8):0.423 (8) ratio. The dihedral angle between the other Cp ring and its attached benzene ring is 13.6 (3)°, and that between the benzene ring and the guanidine group is 64.8 (2)°. One of the N-H groups forms both an intra- and an intermolecular N-H...O hydrogen bond; the other N-H group does not form any hydrogen bonds. In the crystal, pairs of the intermolecular N-H...O hydrogen bonds link the molecules into inversion dimers.

Related literature

For a related structure, see: Bequeath et al. (2007[Bequeath, D. M., Zeller, M., Karnofel, W. J., Hoch, C. L. & Curtin, L. S. (2007). Acta Cryst. E63, m1866-m1867.]). For further synthetic details, see: Gul et al. (2013[Gul, R., Khan, A., Badshah, A., Rauf, M. K., Shah, A., Rahman, Z., Bano, A., Naz, R. & Tahir, M. N. (2013). J. Coord. Chem. 66, 1959-1973.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C25H17Cl3N3O)]

  • Mr = 602.71

  • Monoclinic, P 21 /c

  • a = 17.674 (3) Å

  • b = 6.1352 (12) Å

  • c = 23.961 (5) Å

  • [beta] = 95.359 (9)°

  • V = 2586.8 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.92 mm-1

  • T = 296 K

  • 0.32 × 0.15 × 0.14 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009)[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 0.757, Tmax = 0.882

  • 20020 measured reflections

  • 4828 independent reflections

  • 2612 reflections with I > 2[sigma](I)

  • Rint = 0.088

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.122

  • S = 1.01

  • 4828 reflections

  • 319 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1 0.86 1.97 2.616 (4) 131
N1-H1...O1i 0.86 2.55 3.193 (5) 132
Symmetry code: (i) -x, -y, -z.

Data collection: APEX2 (Bruker, 2009)[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]; cell refinement: SAINT (Bruker, 2009)[Bruker (2009). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7118 ).


Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

Bequeath, D. M., Zeller, M., Karnofel, W. J., Hoch, C. L. & Curtin, L. S. (2007). Acta Cryst. E63, m1866-m1867.  [CSD] [CrossRef] [ChemPort] [details]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gul, R., Khan, A., Badshah, A., Rauf, M. K., Shah, A., Rahman, Z., Bano, A., Naz, R. & Tahir, M. N. (2013). J. Coord. Chem. 66, 1959-1973.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m486  [ doi:10.1107/S1600536813021892 ]

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