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; Chun-Sheng Zhang; Rong Huang; Kun Wei

doi:10.1107/S1600536810028412

. 2010 Jul 24;66(Pt 8):o2092. doi: 10.1107/S1600536810028412

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, Kun Wei ^c,^*

PMCID: PMC3007217 PMID: 21588387

Abstract

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—H⋯O 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,
a = 7.383 (5) Å
b = 13.200 (9) Å
c = 9.843 (7) Å
β = 95.687 (10)°
V = 954.5 (11) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.102

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.136
S = 0.86
1794 reflections
221 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.11 e Å⁻³

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 Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810028412/xu2791sup1.cif

e-66-o2092-sup1.cif^{(22.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028412/xu2791Isup2.hkl

e-66-o2092-Isup2.hkl^{(86.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19C⋯O1ⁱ	0.96	2.55	3.496 (11)	170

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Symmetry code: (i) Inline graphic .

Acknowledgments

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.

supplementary crystallographic information

Comment

Rocuronium is a nondepolarizing neuromuscular blocking agent, which produces neuromuscular blockade by competing with acetylcholine for cholinergic receptors at the motor end plate (Tuba et al., 2002; Auer, 2007). The title compound was obtained as an intermediate during our ongoing investigation of the synthese of rocuronium bromide. In this paper, we report the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. In the molecular structure, the cyclohexene ring displays a half-chair conformtion, the five ring adopts an envelope conformation, and two cyclohexane rings have the normal chair conformation. In the crystal structure weak intermolecular C—H···O hydrogen bonding links the molecules to form the supra-molecular chain running along the [1 0 0] direction (Table 1).

Experimental

The title compound was synthesized according to the procedure reported by Tuba et al. (1980) and by Newaz & Tcholakian (1984). Single crystals were obtained from a mixture of ethyl acetate and petroleum ether by slow evaporation at room temperature.