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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 [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.100
Data-to-parameter ratio = 19.0
Details
Open access

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

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-H...O hydrogen bonds form a double chain along the ab plane interconnected by C-H...O interactions.

Related literature

For applications of steroids as radiodiagnostic compounds and drug delivery systems, see: Katzenellenbogen (1995[Katzenellenbogen, J. A. (1995). J. Nucl. Med. 36, S8-S13.]); Silva et al. (2001[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.]); Wang et al. (2003[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.]). For related compounds, see: Cooper et al. (1969[Cooper, A., Norton, D. A. & Hauptman, H. (1969). Acta Cryst. B25, 814-828.]); Cody et al. (1971[Cody, V., DeJarnette, F., Duax, W. & Norton, D. A. (1971). Acta Cryst. B27, 2458-2468.]); Rajnikant et al. (2006[Rajnikant, Dinesh, & Bhavnaish, C. (2006). Acta Cryst. A62, 136-145.]); Gunasekaran et al. (2009[Gunasekaran, B., Murugan, R., Narayanan, S. S. & Manivannan, V. (2009). Acta Cryst. E65, o73.]). For conformational analysis of ring systems, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]); Duax et al. (1976[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.]).

[Scheme 1]

Experimental

Crystal data
  • C25H25ClO2

  • Mr = 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[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.974

  • 23011 measured reflections

  • 4819 independent reflections

  • 3788 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.100

  • S = 1.02

  • 4819 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2037 Friedel pairs

  • Flack parameter: 0.06 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.82 2.03 2.762 (3) 148
C14A-H14A...O1ii 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[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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.  [CrossRef] [ChemPort] [details]
Cooper, A., Norton, D. A. & Hauptman, H. (1969). Acta Cryst. B25, 814-828.  [CrossRef] [ChemPort] [details]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
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.  [CrossRef] [details]
Gunasekaran, B., Murugan, R., Narayanan, S. S. & Manivannan, V. (2009). Acta Cryst. E65, o73.  [CSD] [CrossRef] [details]
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.  [CrossRef] [details]
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.  [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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.  [ChemPort]


Acta Cryst (2013). E69, o111  [ doi:10.1107/S1600536812050349 ]

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