N′-(4-Hy­droxy­benzyl­idene)ferrocene-1-carbohydrazide

Li, W.; Song, M.; Xu, Y.

doi:10.1107/S1600536811050835

Volume 68
Part 1
Page m8
January 2012

Received 30 October 2011
Accepted 26 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R = 0.047
wR = 0.097
Data-to-parameter ratio = 17.7
Details

N'-(4-Hydroxybenzylidene)ferrocene-1-carbohydrazide

Wen-juan Li,^a Manman Song ^a and Yan Xu ^a ^*

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China
Correspondence e-mail: xuyan@zzu.edu.cn

In the title compound, [Fe(C₅H₅)₂(C₁₃H₁₁N₂O₂)], the dihedral angle between the benzene ring and the cyclopentadiene ring bonded to the carbonyl group is 26.1 (2)°. In the crystal, bifurcated O-H(O,N) and N-HO hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For background to ferrocenylcarbonylhydrazone complexes and the synthesis of the title compound, see: Ma et al. (1988).

Experimental

Crystal data

[Fe(C₅H₅)₂(C₁₃H₁₁N₂O₂)]
M_r = 348.18
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.341 (2) Å
b = 11.669 (2) Å
c = 11.748 (2) Å
V = 1554.7 (5) Å³
Z = 4
Mo K radiation
= 0.98 mm^-1
T = 293 K
0.21 × 0.18 × 0.17 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006) T_min = 0.821, T_max = 0.851
13023 measured reflections
3691 independent reflections
3139 reflections with I > 2(I)
R_int = 0.043

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.097
S = 1.06
3691 reflections
208 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.28 e Å^-3
Absolute structure: Flack (1983), 1583 Friedel pairs
Flack parameter: 0.07 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2BO1ⁱ	0.86	2.20	3.035 (3)	163
O1-H1AO2ⁱⁱ	0.82	2.03	2.838 (3)	170
O1-H1AN1ⁱⁱ	0.82	2.59	3.028 (3)	115
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5370 ).

Acknowledgements

We gratefully acknowledge financial support by the National Natural Science Foundation of China (No. 21171149).

References

Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Ma, Y.-X., Li, F., Sun, H.-S. & Xie, J. (1988). Inorg. Chim. Acta, 149, 209-212.
Rigaku/MSC (2006). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

metal-organic compounds