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Volume 69 
Part 12 
Page m669  
December 2013  

Received 11 November 2013
Accepted 14 November 2013
Online 20 November 2013

Key indicators
Single-crystal X-ray study
T = 292 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.041
wR = 0.112
Data-to-parameter ratio = 16.8
Details
Open access

2-[(Ferrocen-1-yl)(hy­droxy)meth­yl]prop-2-ene­nitrile

aDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India,bLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India, and cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: s_selvanayagam@rediffmail.com

In the title ferrocene derivative, [Fe(C5H5)(C9H8NO)], the dihedral angle between the ene­nitrile group and the substituted cyclo­penta­dienyl ring is 71.2 (1)°. The cyclopentadienyl rings of the ferrocene moiety are arranged in an eclipsed conformation. The hy­droxy group, and the corresponding methine H atom, are disordered over two sets of sites with site-occupancy factors of 0.744 (4) and 0.256 (4). An intra­molecular C-H...O close contact is observed. In the crystal, O-H...N hydrogen bonds form a C(6) chain along [100].

Related literature

For general background to ferrocene derivatives, see: Li et al. (2013[Li, S., Wang, Z., Wei, Y., Wu, C., Gao, S., Jiang, H., Zhao, X., Yan, H. & Wang, X. (2013). Biomaterials, 34, 902-911.]); Skiba et al. (2012[Skiba, J., Rajinisz, A., de Oliveira, K. N., Ott, I., Solecka, J. & Kowalski, K. (2012). Eur. J. Med. Chem. 57, 234-239.]); Karolyi et al. (2012[Karolyi, B. I., Bosze, S., Orban, E., Sohar, P., Drahos, L., Gal, E. & Csampai, A. (2012). Molecules, 17, 2316-2329.]). For related structures, see: Leka et al. (2012a[Leka, Z., Novakovic, S. B., Stevanovic, D., Bogdanovic, G. A. & Vukicevic, R. D. (2012a). Acta Cryst. E68, m229.],b[Leka, Z., Novakovic, S. B., Stevanovic, D., Bogdanovic, G. A. & Vukicevic, R. D. (2012b). Acta Cryst. E68, m230.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C9H8NO)]

  • Mr = 267.10

  • Triclinic, [P \overline 1]

  • a = 7.4317 (15) Å

  • b = 8.0137 (16) Å

  • c = 10.083 (2) Å

  • [alpha] = 92.09 (3)°

  • [beta] = 93.81 (3)°

  • [gamma] = 101.09 (3)°

  • V = 587.3 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.26 mm-1

  • T = 292 K

  • 0.22 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 6351 measured reflections

  • 2683 independent reflections

  • 2481 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.112

  • S = 1.06

  • 2683 reflections

  • 160 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.78 e Å-3

  • [Delta][rho]min = -0.51 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1i 0.82 2.15 2.841 (3) 141
C14-H14B...O1 0.93 2.31 2.648 (4) 101
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2212 ).


Acknowledgements

SS acknowledges the Department of Science and Technology (DST), India, for providing computing facilities under the DST-Fast Track Scheme and also thanks the Vice Chancellor and management of Kalasalingam University, Krishnankoil, for their support and encouragement.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, U. S. A.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Karolyi, B. I., Bosze, S., Orban, E., Sohar, P., Drahos, L., Gal, E. & Csampai, A. (2012). Molecules, 17, 2316-2329.  [ChemPort] [PubMed]
Leka, Z., Novakovic, S. B., Stevanovic, D., Bogdanovic, G. A. & Vukicevic, R. D. (2012a). Acta Cryst. E68, m229.  [CSD] [CrossRef] [IUCr Journals]
Leka, Z., Novakovic, S. B., Stevanovic, D., Bogdanovic, G. A. & Vukicevic, R. D. (2012b). Acta Cryst. E68, m230.  [CSD] [CrossRef] [IUCr Journals]
Li, S., Wang, Z., Wei, Y., Wu, C., Gao, S., Jiang, H., Zhao, X., Yan, H. & Wang, X. (2013). Biomaterials, 34, 902-911.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Skiba, J., Rajinisz, A., de Oliveira, K. N., Ott, I., Solecka, J. & Kowalski, K. (2012). Eur. J. Med. Chem. 57, 234-239.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, m669  [ doi:10.1107/S1600536813031218 ]

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