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Volume 69 
Part 3 
Page m144  
March 2013  

Received 28 January 2013
Accepted 2 February 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.096
Data-to-parameter ratio = 18.9
Details
Open access

(E)-1-Ferrocenyl-3-[2-(2-hydroxyethoxy)phenyl]prop-2-en-1-one

aPost Graduate and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: seshadri_pr@yahoo.com

In the title compound, [Fe(C5H5)(C16H15O3)], the cyclopentadienyl rings are in an eclipsed conformation and the benzene ring makes dihedral angles of 10.84 (9) and 12.35 (9)°, respectively, with the substituted and unsubstituted cyclopentadienyl rings. In the crystal, molecules form inversion dimers through pairs of O-H...O hydrogen bonds. Weak C-H...O hydrogen bonds are observed between the dimers.

Related literature

For the biological activity of ferrocenyl derivatives, see: Jaouen et al. (2004[Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505-2517.]); Fouda et al. (2007[Fouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem. 21, 613-625.]); Biot et al. (2004[Biot, C., Dessolin, J., Richard, I. & Dive, D. (2004). J. Organomet. Chem. 689, 4678-4682.]); Edwards et al. (1975[Edwards, E. I., Epton, R. & Marr, G. (1975). J. Organomet. Chem. 85, C23-C25.]). For a related structure, see: Zora et al. (2006[Zora, M., Açikgöz, C., Tumay, T. A., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. C62, m327-m330.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C5H5)(C16H15O3)]

  • Mr = 376.22

  • Monoclinic, P 21 /c

  • a = 12.5649 (10) Å

  • b = 19.0531 (14) Å

  • c = 7.4930 (6) Å

  • [beta] = 103.932 (3)°

  • V = 1741.1 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.88 mm-1

  • T = 298 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • 16289 measured reflections

  • 4310 independent reflections

  • 3510 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.096

  • S = 1.06

  • 4310 reflections

  • 228 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O3i 0.88 1.98 2.841 (2) 165
C7-H7...O3ii 0.93 2.56 3.409 (3) 152
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.]); 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: SHELXL97 (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: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5242 ).


Acknowledgements

The authors acknowledge the Technology Business Incubator (TBI), CAS in Crystallography, University of Madras, Chennai 600 025, India, for the data collection.

References

Biot, C., Dessolin, J., Richard, I. & Dive, D. (2004). J. Organomet. Chem. 689, 4678-4682.  [CrossRef] [ChemPort]
Bruker (2008). APEX2 and SAINT. Bruker AXS Ins., Madison, Wisconsin, USA.
Edwards, E. I., Epton, R. & Marr, G. (1975). J. Organomet. Chem. 85, C23-C25.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem. 21, 613-625.  [ISI] [CrossRef] [ChemPort]
Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505-2517.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zora, M., Açikgöz, C., Tumay, T. A., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. C62, m327-m330.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, m144  [ doi:10.1107/S1600536813003395 ]

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