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

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.

In the title compound, [Fe(C 5 H 5 )(C 25 H 17 Cl 3 N 3 O)], 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-HÁ Á ÁO hydrogen bond; the other N-H group does not form any hydrogen bonds. In the crystal, pairs of the intermolecular N-HÁ Á ÁO hydrogen bonds link the molecules into inversion dimers.

Related literature
For a related structure, see: Bequeath et al. (2007). For further synthetic details, see: Gul et al. (2013).

Comment
The crystal structure of p-ferrocenylaniline (Bequeath et al., 2007) has been published. As part of our studies in this area, the title compound (I, Fig. 1) has been prepared.

Experimental
The synthesis of the compound (I) was achieved in four steps. In the first step; 4-nitrophenylferrocene was made by the coupling of ferrocene with diazonium salts of nitroaniline using phase transfer catalyst (Gul et al., 2013). In the second step; this nitro phenyl ferrocene was reduced into 4-ferrocenylaniline using palladium on charcoal and hydrazine as reducing agent. In the third step, 3-chlorobenzoyl-3,4-dichlorophenyl thiourea was synthesized by the coupling of substituted aniline with thiocynates in acetone. In the fourth step; the thiourea was mixed with the 4-ferrocenyl aniline in dimethylformamide (DMF) in equimolar ratio with two equivalents of triethylamine (Et 3 N). The temperature was maintained below 278 K using an ice bath and one equivalent of mercuric chloride (HgCl 2 ) was added to the reaction mixture with vigorous stirring. The ice bath was removed after 30 minutes while the stirring continued overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) till the completion of reaction. Chloroform (CHCl 3 , 20 ml) was added to the reaction mixture and the suspension was filtered through a sintered glass funnel to remove the mercuric sulfide (HgS) residue. The solvents from filtrate were evaporated under reduced pressure and residue was re-dissolved in dichloromethane (CH 2 Cl 2 , 20 ml), washed with water (4 × 30 ml) and dried the organic phase over anhydrous magnesium sulfate (MgSO 4 ). The solvent was evaporated and residue was purified by column chromatography to afford orange needles.

Refinement
The non-coordinating ferrocine ring is disordered over two set of sites with refined occupancy ratio of

Figure 1
View of the title compound with displacement ellipsoids drawn at the 50% probability level. Only the major part of disordered ferrocene is shown for clarity.  The partial packing, which shows that molecules form dimers.

2-(3-Chlorobenzoyl)-3-(3,4-dichlorophenyl)-1-(4-ferrocenylphenyl)guanidine
Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. The disordered cyclopentadienyl was refined in two groups as regular pentagons. All the disordered Catoms were treated anisotropically having equal thermal parameters because refinement anisotropically with individual atoms or rings affoarded large ellipsoids. The sides of regular pentagons after final refinement have naearly 1.392 and 1.436 Å. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.   108.0 (9) C16-C15-H15 120.00