17-Deoxoestrone [estra-1,3,5(10)-trien-3-ol]–methanol (3/1)

Ketuly, K.A.; Hadi, A.H.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811013651

Volume 67
Part 5
Pages o1160-o1161
May 2011

Received 11 April 2011
Accepted 11 April 2011
Online 16 April 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.052
wR = 0.141
Data-to-parameter ratio = 9.1
Details

17-Deoxoestrone [estra-1,3,5(10)-trien-3-ol]-methanol (3/1)

Kamal Aziz Ketuly,^a ⁺ A. Hamid A. Hadi,^a Seik Weng Ng ^a and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

Three independent molecules of the title estrone derivative and a molecule of methanol comprise the asymmetric unit of the title compound [systematic name: 13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrocyclopenta[a]phenanthren-3-ol-methanol (3/1)], 3C₁₈H₂₄O·CH₃OH. Two of the estrone molecules exhibit 50:50 disorder (one displays whole-molecule disorder and the other partial disorder in the fused five- and six-membered rings) so that five (partial) molecular conformations are discernable. The conformation of the six-membered ring abutting the aromatic ring is close to a half-chair in all five components. The conformation of the six-membered ring fused to the five-membered ring is based on a chair with varying degrees of distortion ranging from minor to significant. Two distinct conformations are found for the five-membered ring: in four molecules, the five-membered ring is twisted about the bond linking it to the six-membered ring, and in the other, the five-membered ring is an envelope with the quaternary C atom being the flap atom. The crystal packing features O-HO hydrogen bonding whereby the four molecules comprising the asymmetric unit are linked into a supramolecular chain along the b axis.

Related literature

For the original synthesis, see: Huang-Minlon (1949). For geometric and structural features for a series of cholestane derivatives, see: Rajnikant et al. (2006). For background to steroidal estrogen boronic acids and boronates, see: Ketuly & Hadi (2010). For related structures see: Ketuly et al. (1997, 2010).

Experimental

Crystal data

3C₁₈H₂₄O·CH₄O
M_r = 801.16
Monoclinic, C 2
a = 24.3084 (16) Å
b = 7.7235 (5) Å
c = 26.6479 (18) Å
= 114.292 (1)°
V = 4560.1 (5) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 100 K
0.35 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.976, T_max = 0.993
21707 measured reflections
5612 independent reflections
4481 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.141
S = 1.02
5612 reflections
616 parameters
234 restraints
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O3	0.84	1.83	2.662 (3)	170
O2-H2O4	0.84	1.82	2.655 (4)	170
O3-H3O2	0.84	1.88	2.711 (3)	173
O4-H4O1ⁱ	0.84	1.90	2.736 (4)	178
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMOL (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5844 ).

Acknowledgements

The authors thank the University of Malaya for support and greatly appreciate UMRG grant No. RG035/10BIO.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.
Huang-Minlon (1949). J. Am. Chem. Soc. 71, 3301-3303.
Ketuly, K. A. & Hadi, A. H. (2010). Molecules, 15, 2347-2356.
Ketuly, K. A., Hadi, A. H. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2265.
Ketuly, K. A., Yufit, D. S., Brooks, C. J. W. & Freer, A. A. (1997). Acta Cryst. C53, 981-982.
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.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds