(E)-3-Hydr­oxy-13-methyl-16-[4-(methyl­sulfan­yl)benzyl­idene]-7,8,9,11,12,13,15,16-octa­hydro-6H-cyclo­penta­[a]phen­an­­­­thren-17(14H)-one

Gunasekaran, B.; Murugan, R.; Narayanan, S.S.; Manivannan, V.

doi:10.1107/S1600536808040877

Volume 65
Part 1
Page o73
January 2009

Received 27 November 2008
Accepted 3 December 2008
Online 10 December 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.049
wR = 0.142
Data-to-parameter ratio = 12.9
Details

(E)-3-Hydroxy-13-methyl-16-[4-(methylsulfanyl)benzylidene]-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one

B. Gunasekaran,^a R. Murugan,^b S. Sriman Narayanan ^b and V. Manivannan ^c ^*

^aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India,^bDepartment of Analytical Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cReader in Physics, Presidency College, Chennai 600 005, India
Correspondence e-mail: manivan_1999@yahoo.com

In the title compound, C₂₆H₂₈O₂S, the dihedral angles between the mean plane of the five membered ring and the 4-(methylsulfanyl)benzylidine ring in the two crystallographically independent molecules are 34.05 (10) and 40.53 (15)°. The packing is stabilized by intermolecular O-HO and C-HO interactions.

Related literature

For the biological activity of testosterone derivatives, see: Alvarez-Ginarte et al. (2005). For puckering parameters, see: Cremer & Pople (1975). For related structures, see: Suitchmezian et al. (2007); Ye (2007).

Experimental

Crystal data

C₂₆H₂₈O₂S
M_r = 404.54
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.9654 (3) Å
b = 13.0262 (4) Å
c = 27.9441 (8) Å
V = 4355.5 (2) Å³
Z = 8
Mo K radiation
= 0.17 mm^-1
T = 293 (2) K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.959, T_max = 0.975
21727 measured reflections
6847 independent reflections
4775 reflections with I > 2(I)
R_int = 0.040
_max = 24.1°

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.142
S = 1.06
6847 reflections
529 parameters
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.30 e Å^-3
Absolute structure: Flack (1983), 2995 Friedel pairs
Flack parameter: -0.06 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.82	1.95	2.746 (3)	163
C10-H10O2ⁱ	0.93	2.53	3.179 (4)	127
O3-H3AO4ⁱⁱ	0.82	2.03	2.830 (4)	166
C36-H36O4ⁱⁱ	0.93	2.47	3.209 (4)	136
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, 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, 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2822 ).

Acknowledgements

BG thanks AMET University management, India, for their kind support.

References

Alvarez-Ginarte, Y. M., Crespo, R., Montero-Cabrera, L. A., Ruiz-Garcia, J. A., Ponce, Y. M., Santana, R., Pardillo-Fontdevila, E. & Alonso-Becerra, E. (2005). QSAR Comb. Sci. 24, 218-226.
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Suitchmezian, V., Jess, I. & Näther, C. (2007). Acta Cryst. E63, o4839.
Ye, Y.-Y. (2007). Acta Cryst. E63, o3022.

organic compounds