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

Paramasivam, S.; Purushothaman, S.; Seshadri, P.R.; Raghunathan, R.

doi:10.1107/S1600536813003395

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 (C-C) = 0.003 Å
R = 0.035
wR = 0.096
Data-to-parameter ratio = 18.9
Details

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

S. Paramasivam,^a Santhanagopalan Purushothaman,^b P. R. Seshadri ^a ^* and Raghavachary Raghunathan ^b

^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-HO hydrogen bonds. Weak C-HO hydrogen bonds are observed between the dimers.

Related literature

For the biological activity of ferrocenyl derivatives, see: Jaouen et al. (2004); Fouda et al. (2007); Biot et al. (2004); Edwards et al. (1975). For a related structure, see: Zora et al. (2006).

Experimental

Crystal data

[Fe(C₅H₅)(C₁₆H₁₅O₃)]
M_r = 376.22
Monoclinic, P 2₁ /c
a = 12.5649 (10) Å
b = 19.0531 (14) Å
c = 7.4930 (6) Å
= 103.932 (3)°
V = 1741.1 (2) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.096
S = 1.06
4310 reflections
228 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O3ⁱ	0.88	1.98	2.841 (2)	165
C7-H7O3ⁱⁱ	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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.
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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Fouda, M. F. R., Abd-Elzaher, M. M., Abdelsamaia, R. A. & Labib, A. A. (2007). Appl. Organomet. Chem. 21, 613-625.
Jaouen, G., Top, S., Vessireres, A., Leclercq, G., Vaissermann, J. & McGlinchey, M. J. (2004). Curr. Med. Chem. 11, 2505-2517.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Zora, M., Açikgöz, C., Tumay, T. A., Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. C62, m327-m330.

metal-organic compounds