N′-Ferrocenyl-2-hydroxy­benzohydrazide

Ying Xu; Chun-Ling Chen; Jing Zhou; Ming-Xue Li

doi:10.1107/S1600536807065634

. 2007 Dec 12;64(Pt 1):m177. doi: 10.1107/S1600536807065634

N′-Ferrocenyl-2-hydroxybenzohydrazide

Ying Xu ^a, Chun-Ling Chen ^a, Jing Zhou ^a, Ming-Xue Li ^a,^*

PMCID: PMC2915112 PMID: 21200525

Abstract

The title complex, [Fe(C₅H₅)(C₁₃H₁₁N₂O₃)], was prepared via self-assembly using ferrocenyl hydrazide and ethyl salicylate. The compound is potentially a tridentate ferrocene-based ligand. The conformation of the molecule allows the formation of an intramolecular N—H⋯O hydrogen bond involving the hydroxyl group. The CONHNHCO unit and the rings bonded to it are nearly coplanar. The crystal structure is stabilized by intermolecular O—H⋯O(carbonyl) and N—H⋯O(carbonyl) hydrogen bonds.

Related literature

For related literature about applications of ferrocene complexes, see: Beer (1992 ▶); Beer & Smith (1997 ▶); Long (1995 ▶); Miller & Epstein (1994 ▶); Nguyen et al. (1999 ▶).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₃H₁₁N₂O₃)]
M _r = 364.18
Monoclinic,
a = 20.680 (3) Å
b = 9.9673 (15) Å
c = 16.941 (3) Å
β = 121.704 (3)°
V = 2970.8 (8) Å³
Z = 8
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 293 (2) K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.820, T _max = 0.852
7479 measured reflections
2611 independent reflections
1053 reflections with I > 2σ(I)
R _int = 0.129

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.086
S = 0.57
2611 reflections
230 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065634/bh2153sup1.cif

e-64-0m177-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065634/bh2153Isup2.hkl

e-64-0m177-Isup2.hkl^{(128.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O3	0.860 (10)	1.95 (2)	2.631 (4)	135 (3)
O3—H3B⋯O1ⁱ	0.822 (10)	1.908 (15)	2.705 (4)	163 (4)
N1—H1B⋯O2ⁱⁱ	0.871 (10)	2.03 (2)	2.810 (4)	148 (4)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was financially supported by the Foundation of the Educational Department of Henan Province (No. 2007150012).

supplementary crystallographic information

Comment

The synthesis, isolation and characterization of ferrocene in 1951 marked an important milestone in the evolution of modern organometallic chemistry. Potential applications in material sciences, such as molecular sensors (Beer, 1992; Beer & Smith, 1997), molecular magnetic materials (Miller & Epstein, 1994), and nonlinear optical materials (Nguyen et al., 1999; Long, 1995) attracted much attention. We report here the crystal structure of the title compound, (I), a new ferrocene-based complex (Fig. 1).

The title compound belongs to space group C2/c. The bond lengths O1?C11 and O2?C12 are 1.240 (5) and 1.233 (4) Å, respectively, as excepted for double bonds. The bond length O3—C18, 1.349 (5) Å, corresponds to a single bond. The N1—C11 and N2—C12 bond distances are 1.340 (5) and 1.343 (5) Å, respectively, which make clear they are in the normal range for N—C single bonds. The bond length N1—N2 = 1.381 (4) Å is also consistent with a single N—N bond. An intramolecular N2—H2B···O3 hydrogen bond is observed in the molecular structure.

In the crystal, molecules are connected by intermolecular hydrogen bonds involving carbonyl O atoms O2 and O3 as acceptor and N—H or O—H groups as donors.

Experimental

All reagents were commercially available and of analytical grade. Ferrocenyl hydrazide (1.22 g, 5 mmol) and ethyl salicylate (0.83 g, 5 mmol) were mixed in ethanol and refluxed for 7 h. The resulting red solid was filtered, washed with ethanol and dried under reduced pressure. Anal. Calc. for C₁₈H₁₆FeN₂O₃: C 59.37, H 4.43, N 7.69%. Found: C 59.48, H 4.31, N 7.52%.