6-Ferrocenoyl-7-(4-fluorophenyl)spiro[hexahydropyrrolo[1,2-c][1,3]thiazole-5,11′-indeno[1,2-b]quinoxaline]

In the title compound, [Fe(C5H5)(C32H23FN3OS)], both the thiazolidine ring and the pyrrolidine ring adopt a twist conformation on the N—C(H) bridging bond. Their mean planes are inclined to one another by 10.05 (10)°, and they make dihedral angles of 82.09 (10) and 89.67 (11)°, respectively, with the cyclopentane ring. The F atom deviates by −0.0238 (2) Å from the benzene ring to which it is attached. In the crystal, molecules are linked by a pair of C—H⋯O hydrogen bonds, forming inversion dimers.

In the title compound, [Fe(C 5 H 5 )(C 32 H 23 FN 3 OS)], both the thiazolidine ring and the pyrrolidine ring adopt a twist conformation on the N-C(H) bridging bond. Their mean planes are inclined to one another by 10.05 (10) , and they make dihedral angles of 82.09 (10) and 89.67 (11) , respectively, with the cyclopentane ring. The F atom deviates by À0.0238 (2) Å from the benzene ring to which it is attached. In the crystal, molecules are linked by a pair of C-HÁ Á ÁO hydrogen bonds, forming inversion dimers.

Comment
Ferrocene attached compounds are well known to have biological activities, such as antimalarial, antifungal (Biot et al., 2004), antitumor (Jaouen et al., 2004), and antibacterial (Fouda et al., 2007). Against this background, and in order to gain information on the molecular conformations and crystal packing, we report herein on the synthesis and crystal structure of the title compound.
In the title compound, Fig. 1, both the thiazolidine ring and the pyrrolidine ring adopt a twist conformation on bond N3-C18. The thiazolidine ring (S1/N3/C18-C20) mean plane makes a dihedral angle of 10.05 (10)° with the pyrrolidine ring (N3/C15-C18) mean plane, it also makes a dihedral angle of 82.09 (10)° with the cyclopentane ring (C7-C9/C14/C15) which shows that they are almost perpendicular to each other. The pyrrolidine ring mean plane makes a dihedral angle of 89.67 (11)° with the cyclopentane ring which shows they too are almost orthogonal to each other. The fluorine atom F1 attached with the phenyl ring (C21-C26) deviates by -0.0238 (2)Å.
In the crystal, molecules are linked by a pair of C-H···O hydrogen bonds forming inversion dimers (Table 1 and Fig. 2).

Experimental
Ninhydrin (1 mmol) and 1, 2-phenylenediamine (1 mmol) were mixed and stirred with 10 ml of methanol for 10 min. To this mixture 1 mmol of thioproline and 1-ferrocenyl-3-(4-fluoro) phenyl prop-2-ene-1-one dipolarophile were added and the mixture was refluxed up to the end of the reaction as observed by TLC. The solvent content from the mixture was removed under reduced pressure and the crude product was obtained. Using column chromatography the crude extract was purified with a 4:1 ratio of petroleum ether and ethyl acetate. Finally, single crystals suitable for the X-ray diffraction were obtained by slow evaporation of the solvent at room temperature.

Refinement
Hydrogen atoms were placed in calculated positions with C-H ranging from 0.93 -0.98 Å and refined using the riding model approximation with U iso (H) = 1.2U eq (C).

Computing details
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009   The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.  The crystal packing of the title compound viewed along the a axis. The C-H···O hydrogen bonds are shown as dashed lines (see Table 1 for details; H-atoms not involved in hydrogen bonding have been omitted for clarity).

6-Ferrocenoyl-7-(4-fluorophenyl)spiro[hexahydropyrrolo[1,2-c][1,3]thiazole-5,11′-indeno[1,2-b]quinoxaline]
Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. 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 > 2sigma(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.