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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 [sigma](C-C) = 0.006 Å
R = 0.047
wR = 0.097
Data-to-parameter ratio = 17.7
Details
Open access

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

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-H...O 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[Ma, Y.-X., Li, F., Sun, H.-S. & Xie, J. (1988). Inorg. Chim. Acta, 149, 209-212.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)2(C13H11N2O2)]

  • Mr = 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[alpha] radiation

  • [mu] = 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[Rigaku/MSC (2006). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.821, Tmax = 0.851

  • 13023 measured reflections

  • 3691 independent reflections

  • 3139 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.097

  • S = 1.06

  • 3691 reflections

  • 208 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1583 Friedel pairs

  • Flack parameter: 0.07 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2B...O1i 0.86 2.20 3.035 (3) 163
O1-H1A...O2ii 0.82 2.03 2.838 (3) 170
O1-H1A...N1ii 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[Rigaku/MSC (2006). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]).


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.  [CrossRef] [details]
Ma, Y.-X., Li, F., Sun, H.-S. & Xie, J. (1988). Inorg. Chim. Acta, 149, 209-212.  [ChemPort]
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.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, m8  [ doi:10.1107/S1600536811050835 ]

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