10,13-Dimethyl-16-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetra­deca­hydro-1H-cyclo­penta­[a]phenanthren-17-yl acetate

Shi, R.; Zhang, C.-S.; Huang, R.; Wei, K.

doi:10.1107/S1600536810028412

Volume 66
Part 8
Page o2092
August 2010

Received 29 June 2010
Accepted 15 July 2010
Online 24 July 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.010 Å
R = 0.053
wR = 0.136
Data-to-parameter ratio = 8.1
Details

10,13-Dimethyl-16-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

Rui Shi,^a Chun-Sheng Zhang,^b Rong Huang ^c and Kun Wei ^c ^*

^aKey Laboratory of Forest Resources Conservation and Use in the Southwest Mountains of China (Ministry of Education), Southwest Forestry University, Kunming 650224, People's Republic of China,^bZhejiang Apeloa Kangyu Pharmaceutical Co Ltd, Jinhua 322118, People's Republic of China, and ^cSchool of Chemical Science and Technology, Key Laboratory of Medicinal Chemistry for Natural Resources (Ministry of Education), Yunnan University, Kunming 650091, People's Republic of China
Correspondence e-mail: kunwei2008@126.com

In the title compound, C₂₁H₃₀O₃, the five-membered ring adopts an envelope conformation, the cyclohexene ring displays a half-chair conformation and the two cyclohexane rings have normal chair conformations. In the crystal structure, weak intermolecular C-HO hydrogen bonding links the molecules into supramolecular chains running along [100].

Related literature

Rocuronium is a non-depolarizing neuromuscular blocking agent. The title compound was obtained as an intermediate during our ongoing investigation of the synthesis of rocuronium bromide; for further information on rocuronium bromide, see: Tuba et al. (2002); Auer (2007). For the synthesis, see: Tuba (1980); Newaz & Tcholakian (1984).

Experimental

Crystal data

C₂₁H₃₀O₃
M_r = 330.45
Monoclinic, P 2₁
a = 7.383 (5) Å
b = 13.200 (9) Å
c = 9.843 (7) Å
= 95.687 (10)°
V = 954.5 (11) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.45 × 0.40 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer
5527 measured reflections
1794 independent reflections
864 reflections with I > 2(I)
R_int = 0.102

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.136
S = 0.86
1794 reflections
221 parameters
1 restraint
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.11 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C19-H19CO1ⁱ	0.96	2.55	3.496 (11)	170
Symmetry code: (i) x-1, y, z.

Data collection: SMART (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: 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: XU2791 ).

Acknowledgements

The authors gratefully acknowledge computing time provided by the X-ray Diffraction Analysis Centre of the Key Laboratory of Medicinal Chemistry for Natural Resources (Ministry of Education), Yunnan University, China.

References

Auer, U. (2007). Vet. J. 173, 422-427.
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Newaz, S. N. & Tcholakian, R. K. (1984). Steroids, 43, 445-456.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tuba, Z. (1980). Arzneim. Forschung. 30, 342-346.
Tuba, Z., Maho, S. & Vizi, S. (2002). Curr. Med. Chem. 9, 1507-1536.

organic compounds