Ethyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-methyl­ene-14-oxotetra­cyclo­[11.2.1.01,10.04,9]hexa­decane-5-carboxyl­ate

Shi, H.

doi:10.1107/S1600536809053380

Volume 66
Part 1
Page o154
January 2010

Received 16 November 2009
Accepted 11 December 2009
Online 16 December 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.010 Å
R = 0.067
wR = 0.189
Data-to-parameter ratio = 7.5
Details

Ethyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-methylene-14-oxotetracyclo[11.2.1.0^1,10.0^4,9]hexadecane-5-carboxylate

Hao Shi ^a ^*

^aThe College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: shihao@zjut.edu.cn

The title compound, C₂₂H₃₄O₃, was synthesized from isosteviol. The asymmetric unit contains of two independent molecules with the same absolute configurations. In both the molecules, the three six-membered rings adopt chair conformations, the stereochemistry of the A/B and B/C ring junctions are trans, and the five-membered ring D adopts an envelope conformation.

Related literature

Since the title compound was prepared from isosteviol, the configuration can be deduced from the known chirality of the isosteviol, see: Rodrigues & Lechat (1988), Xue et al. (1993). For the pharmacological activity of isosteviol, see: Liu et al. (2001); Mizushina et al. (2005); Wong et al. (2004); Zhang & Xu (2004). For ring conformations, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₂H₃₄O₃
M_r = 346.49
Triclinic, P 1
a = 6.5365 (9) Å
b = 12.5639 (15) Å
c = 13.1212 (16) Å
= 69.174 (1)°
= 87.518 (2)°
= 79.018 (1)°
V = 988.4 (2) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.49 × 0.42 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999) T_min = 0.964, T_max = 0.989
5226 measured reflections
3451 independent reflections
1824 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.067
wR(F²) = 0.189
S = 0.90
3451 reflections
459 parameters
3 restraints
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.27 e Å^-3

Table 1
Comparison of the puckering parameters (Å, °) for the six and five-membered rings in molecules 1 and 2

Molecule		1			2
Puckering parameters	Q			Q
Ring A1, A2	0.536 (7)	180.0 (7)	273 (27)	0.545 (8)	177.2 (8)	251 (29)
Ring B1, B2	0.557 (7)	9.5 (7)	72 (4)	0.561 (7)	7.8 (7)	71 (5)
Ring C1, C2	0.633 (7)	164.8 (6)	120 (3)	0.646 (8)	163.2 (7)	131 (2)
Puckering parameters		q₂	₂		q₂	₂
Ring D1, D2		0.467 (8)	333.7 (10)		0.452 (8)	332.2 (11)
Ring A1 atoms C2-C7, A2 C24-C29, B1 C6-C11, B2 C28-C33, C1 C10-C14/C17, C2 C32-C36/C39, D1 C14-C16/C10/C17 and D2 C36-C38/C32/C39.

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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); software used to prepare material for publication: SHELXL97 nd PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2514 ).

Acknowledgements

This material is based upon work funded by the Zhejiang Provincial Natural Science Foundation of China under grant No. Y2090552 and the Open Foundation of Key Disciplines within the Zhejiang Provincial Key Disciplines.

References

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