N-(4-Ferrocenylphenyl)benzamide

In the title compound, [Fe(C5H5)(C18H14NO)], the unsubstituted cyclopentadienyl ring is disordered over two sets of sites with occupancy ratio of 0.55 (1):0.45 (1). One conformation has the rings eclipsed and the other staggered. An intramolecular C—H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, intermolecular C—H⋯O and N—H⋯O hydrogen bonds lead to R 2 1(7) ring motifs. The molecules are linked into polymeric chains extending along the b axis.

In the title compound, [Fe(C 5 H 5 )(C 18 H 14 NO)], the unsubstituted cyclopentadienyl ring is disordered over two sets of sites with occupancy ratio of 0.55 (1):0.45 (1). One conformation has the rings eclipsed and the other staggered. An intramolecular C-HÁ Á ÁO hydrogen bond forms an S(6) ring motif. In the crystal, intermolecular C-HÁ Á ÁO and N-HÁ Á ÁO hydrogen bonds lead to R 2 1 (7) ring motifs. The molecules are linked into polymeric chains extending along the b axis.
In (I) the cyclopentadienyl ring A (C6-C10), phenyl rings B (C11-C16) and C (C18-C23) are planar with r. m. s. deviations of 0.0024, 0.0020 and 0.0030 Å, respectively. The dihedral angle between A/B is 2.31 (23)° which shows that central phenyl ring is almost planar with attached cyclopentadienyl. The dihedral angle between B/C is 69.05 (8)°. The Fe-atom is at a distance of 1.6435 (17) Å from the centroid of ring A. The important bond distances [Fe-C] and bond angles [C-Fe-C] are given in Table 1. Cyclopentadienyl ring of ferrocene not attached with 4-(benzoylamino)phenyl is disordered over two set of sites with occupancy ratio of 0.548 (14):0.452 (14). There exist intramolecular H-bonding of C-H···O type forming S (6) ring motif (Bernstein et al., 1995). The intermolecular H-bondings of C-H···O and N-H···O type complete R 2 1 (7) ring motif ( Table 2, Fig. 2). The molecules are stabilized in the form of polymeric chains extending along the crystallographic b axis (Fig. 2). In these chains molecules are connected in helical way due to screw symmetry.
The completion of reaction monitored through TLC. To remove extra triethylamine and un-reacted acid chloride and the formed ammonium chloride, the mixture was extracted with distilled water (6 × 100 ml). The solution was evaporated under reduced pressure to give orange solid and re-crystallized form CH 2 Cl 2 . (yield: 84%)

Refinement
The disordered cyclopentadienyl was refined in two groups as regular pentagons of 1.42 Å. The anisotropic temperature factors of the disordered C atoms were restrained to be nearly isotropic.
The H-atoms were positioned geometrically (N-H = 0.86 Å, C-H = 0.93 Å) and refined as riding with U iso (H) = xU eq (C, N), where x = 1.2 for all H-atoms. Fig. 1. View of (I) with the atom numbering scheme having atoms of greater occupancy ratio. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. The dotted lines indicate the intra-molecular H-bondings.