(E)-16-(4-Chloro­benzyl­idene)estrone

Suresh, J.; Thenmozhi, H.; Jeyachandran, V.; Kumar, R.R.; Lakshman, P.L.N.

doi:10.1107/S1600536812050349

Volume 69
Part 1
Page o111
January 2013

Received 25 November 2012
Accepted 10 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.100
Data-to-parameter ratio = 19.0
Details

(E)-16-(4-Chlorobenzylidene)estrone

J. Suresh,^a H. Thenmozhi,^a Veerappan Jeyachandran,^b R. Ranjith Kumar ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India,^bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
Correspondence e-mail: plakshmannilantha@ymail.com

In the title compound, C₂₅H₂₅ClO₂, the C ring adopts a chair conformation, while the B ring approximates a half-chair conformation. The five-membered ring D has a twist conformation on the C-C bond fused with the C ring. Aromatic rings A and E are not coplanar, as evidenced by the dihedral angle of 7.51 (1)°. In the crystal, O-HO hydrogen bonds form a double chain along the ab plane interconnected by C-HO interactions.

Related literature

For applications of steroids as radiodiagnostic compounds and drug delivery systems, see: Katzenellenbogen (1995); Silva et al. (2001); Wang et al. (2003). For related compounds, see: Cooper et al. (1969); Cody et al. (1971); Rajnikant et al. (2006); Gunasekaran et al. (2009). For conformational analysis of ring systems, see: Cremer & Pople (1975); Duax et al. (1976).

Experimental

Crystal data

C₂₅H₂₅ClO₂
M_r = 392.90
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.3601 (3) Å
b = 11.2012 (6) Å
c = 28.3043 (14) Å
V = 2016.42 (18) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 293 K
0.17 × 0.15 × 0.13 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.967, T_max = 0.974
23011 measured reflections
4819 independent reflections
3788 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.100
S = 1.02
4819 reflections
253 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.26 e Å^-3
Absolute structure: Flack (1983), 2037 Friedel pairs
Flack parameter: 0.06 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.82	2.03	2.762 (3)	148
C14A-H14AO1ⁱⁱ	0.96	2.55	3.454 (3)	157
Symmetry codes: (i) x-1, y-1, z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2467 ).

Acknowledgements

JS thanks the UGC for the FIST support. JS and HT thank the management of Madura College for their encouragement and support. RRK thanks the DST, New Delhi for funds under the fast-track scheme (No. SR/FT/CS-073/2009)

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cody, V., DeJarnette, F., Duax, W. & Norton, D. A. (1971). Acta Cryst. B27, 2458-2468.
Cooper, A., Norton, D. A. & Hauptman, H. (1969). Acta Cryst. B25, 814-828.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, Vol. 9, edited by E. L. Elliel & N. Allinger, pp. 271-383. New York: John Wiley.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gunasekaran, B., Murugan, R., Narayanan, S. S. & Manivannan, V. (2009). Acta Cryst. E65, o73.
Katzenellenbogen, J. A. (1995). J. Nucl. Med. 36, S8-S13.
Rajnikant, Dinesh, & Bhavnaish, C. (2006). Acta Cryst. A62, 136-145.
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Silva, M. C. M. E., Patricio, L., Gano, L., Melo, M. L. S. E., Inohae, E., Mataka, S. & Thiemann, T. (2001). Appl. Radiat. Isot. 54, 227-239.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, J., Watanabe, M., Mataka, S., Thiemann, T., Morais, G. R., Roleira, F., da Silva, E. T. & Silva, C. M. E. (2003). Z. Naturforsch. Teil B, 58, 799-804.

organic compounds