(IUCr) 2'-Methylpyrazolo[4',3':16,17]androst-5-en-3[beta]-ol

Volume 65
Part 6
Page o1436
June 2009

Received 15 May 2009
Accepted 22 May 2009
Online 29 May 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.065
wR = 0.178
Data-to-parameter ratio = 11.8
Details

2'-Methylpyrazolo[4',3':16,17]androst-5-en-3-ol

Hu-ling Zheng,^a Peng Xia ^a and Ying Chen ^a ^*

^aDepartment of Medicinal Chemistry, School of Pharmacy, Fudan University, 138 Yixueyuan Road Shanghai 200032, People's Republic of China
Correspondence e-mail: yingchen71@fudan.edu.cn

In the title compound, C₂₁H₃₀N₂O, there are five fused rings. The A and C rings adopt chair conformations, ring B adopts an 8 [beta] ,9 [alpha] -half-chair conformation and ring D adopts a 14 [alpha] -envelope conformation. The pyrazole ring is planar. Intermolecular O-HN hydrogen bonds [HN = 1.88 (5) Å] help to stabilize the crystal structure. The absolute structure was deduced from those of the starting materials.

Related literature

For general background, see: Kashiwada et al. (1996); Spek (2009).

Experimental

Crystal data

C₂₁H₃₀N₂O
M_r = 326.47
Orthorhombic, P 2₁ 2₁ 2
a = 11.779 (4) Å
b = 27.996 (10) Å
c = 6.361 (2) Å
V = 2097.6 (12) Å³
Z = 4
Mo K radiation
= 0.06 mm^-1
T = 293 K
0.20 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.988, T_max = 0.995
10038 measured reflections
2633 independent reflections
1670 reflections with I > 2(I)
R_int = 0.089

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.178
S = 0.99
2633 reflections
224 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N2ⁱ	0.96 (5)	1.88 (6)	2.813 (5)	163 (5)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2148 ).

Acknowledgements

The authors acknowledge Miss Wang Jingmei, Center of Analysis and Measurement, Fudan University, for her help with the crystal structure analysis.

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kashiwada, Y., Hashimoto, F. & Cosentino, L. M. (1996). J. Med. Chem. 39, 1016-1017.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds