Ethyl 3-hydr­oxy-13-methyl-4′-phenyl-2′-(3,4,5-trimethoxy­phen­yl)-6,7,8,9,11,12,13,14,15,16-deca­hydro­spiro­[cyclo­penta­[a]phenanthrene-16,3′-pyrrolidine]-5′-carboxyl­ate

Kamala, E.T.S.; Murugan, R.; Nirmala, S.; Sudha, L.; Narayanan, S.S.

doi:10.1107/S1600536808034582

Volume 64
Part 11
Pages o2219-o2220
November 2008

Received 5 October 2008
Accepted 23 October 2008
Online 31 October 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.047
wR = 0.132
Data-to-parameter ratio = 8.1
Details

Ethyl 3-hydroxy-13-methyl-4'-phenyl-2'-(3,4,5-trimethoxyphenyl)-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-16,3'-pyrrolidine]-5'-carboxylate

E. Theboral Sugi Kamala,^a R. Murugan,^b S. Nirmala,^a L. Sudha ^c ^* and S. Sriman Narayanan ^b

^aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India,^bDepartment of Analytical Chemistry, University of Madras, Guindy Campus, Chennai 600025, India, and ^cDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India
Correspondence e-mail: sudharose18@gmail.com

In the title compound, C₃₉H₄₅NO₇,the pyrrolidine ring is connected to an estrone group, a trimethoxy benzene and a phenyl ring. The pyrrolidine ring exhibits a twist conformation and the other five-membered ring an envelope conformation. Molecules are linked by N-HO hydrogen bonds, C-H [pi] interactions and C-HO hydrogen bonds.

Related literature

For general background, see: García-Peláez et al. (2004); Holland and Roy (1995); Obniska et al. (2002); Suzuki et al. (1994). For bond-length data, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983).

Experimental

Crystal data

C₃₉H₄₅NO₇
M_r = 639.76
Monoclinic, C 2
a = 26.1776 (6) Å
b = 10.3379 (2) Å
c = 13.6631 (3) Å
= 91.1250 (10)°
V = 3696.82 (14) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 (2) K
0.30 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (Blessing, 1995) T_min = 0.977, T_max = 0.981
38566 measured reflections
3462 independent reflections
3186 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.132
S = 1.11
3462 reflections
425 parameters
319 restraints
H-atom parameters constrained
_max = 0.48 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AN1ⁱ	0.82	1.99	2.782 (4)	163
C39-H39AO3ⁱⁱ	0.96	2.56	3.378 (4)	144
C29-H29ACg1ⁱⁱⁱ	0.96	3.00	3.820 (4)	144
Symmetry codes: (i) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2805 ).

Acknowledgements

ETSK thanks Professor M. N. Ponnuswamy and Professor D. Velmurugan, Department of Crystallography and Biophysics, University of Madras, India, for their guidance and valuable suggestions. ETSK also thanks SRM Management for their support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Bruker (2004). SMART, SAINT and XPREP. Bruker AXS Inc., Madison,Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
García-Peláez, B., Ferrer-Lorente, R., Gómez-Ollés, S., Fernández-López, J. A., Remesar, X. & Alemany, M. (2004). J. Dairy Sci. 87, 2331-2336.
Holland, M. B. & Roy, D. (1995). Carcinogenesis, 16, 1955-1961.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Obniska, J., Zeic, A. & Zagorska, A. (2002). Acta Pol. Pharm. 59, 209-213.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Suzuki, T., Nagasu Kawai, H., Fujiwara, K. & Tsuji, T. (1994). Tetrahedron Lett, 44, 6095-6098.

organic compounds