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

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o2092

https://doi.org/10.1107/S1600536810028412

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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

(Received 29 June 2010; accepted 15 July 2010; online 24 July 2010)

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, P 2₁
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[F² > 2σ(F²)] = 0.053
wR(F²) = 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

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
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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810028412/xu2791Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Structure description top

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).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom labelling scheme and 30% probability displacement ellipsoids.

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 top

Crystal data top

C₂₁H₃₀O₃	F(000) = 360
M_r = 330.45	D_x = 1.150 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 864 reflections
a = 7.383 (5) Å	θ = 5.7–25.7°
b = 13.200 (9) Å	µ = 0.08 mm⁻¹
c = 9.843 (7) Å	T = 293 K
β = 95.687 (10)°	Block, colorless
V = 954.5 (11) Å³	0.45 × 0.40 × 0.32 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	864 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.102
Graphite monochromator	θ_max = 25.2°, θ_min = 2.1°
φ and ω scans	h = −8→8
5527 measured reflections	k = −9→15
1794 independent reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0539P)²] where P = (F_o² + 2F_c²)/3
S = 0.86	(Δ/σ)_max < 0.001
1794 reflections	Δρ_max = 0.13 e Å⁻³
221 parameters	Δρ_min = −0.11 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (3)

Crystal data top

C₂₁H₃₀O₃	V = 954.5 (11) Å³
M_r = 330.45	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.383 (5) Å	µ = 0.08 mm⁻¹
b = 13.200 (9) Å	T = 293 K
c = 9.843 (7) Å	0.45 × 0.40 × 0.32 mm
β = 95.687 (10)°

Data collection top

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

Refinement top

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

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2353 (9)	0.8413 (7)	0.3971 (7)	0.089 (2)
H1A	0.1047	0.8316	0.3809	0.107*
H1B	0.2756	0.8100	0.4841	0.107*
C2	0.2742 (13)	0.9525 (7)	0.4068 (8)	0.104 (3)
H2	0.1975	0.9938	0.4519	0.125*
C3	0.4149 (14)	0.9942 (7)	0.3531 (9)	0.109 (3)
H3	0.4306	1.0640	0.3597	0.130*
C4	0.5469 (11)	0.9345 (7)	0.2835 (8)	0.100 (2)
H4A	0.6690	0.9545	0.3187	0.120*
H4B	0.5318	0.9506	0.1868	0.120*
C5	0.5277 (9)	0.8189 (6)	0.3009 (7)	0.084 (2)
H5	0.5753	0.8028	0.3949	0.100*
C6	0.6463 (9)	0.7619 (6)	0.2068 (8)	0.090 (2)
H6A	0.6053	0.7772	0.1123	0.108*
H6B	0.7716	0.7842	0.2245	0.108*
C7	0.6356 (8)	0.6477 (6)	0.2303 (7)	0.087 (2)
H7A	0.7052	0.6129	0.1660	0.104*
H7B	0.6896	0.6319	0.3217	0.104*
C8	0.4396 (8)	0.6097 (5)	0.2132 (6)	0.0669 (18)
H8	0.3895	0.6192	0.1181	0.080*
C9	0.3222 (8)	0.6712 (6)	0.3088 (6)	0.0703 (19)
H9	0.3770	0.6599	0.4023	0.084*
C10	0.3266 (8)	0.7864 (5)	0.2843 (6)	0.0674 (18)
C11	0.1274 (8)	0.6266 (6)	0.3010 (7)	0.083 (2)
H11A	0.0603	0.6610	0.3673	0.100*
H11B	0.0660	0.6400	0.2111	0.100*
C12	0.1231 (9)	0.5120 (7)	0.3282 (7)	0.089 (2)
H12A	0.1719	0.4987	0.4217	0.107*
H12B	−0.0019	0.4884	0.3170	0.107*
C13	0.2347 (8)	0.4539 (5)	0.2304 (6)	0.0716 (19)
C14	0.4277 (8)	0.4979 (5)	0.2504 (6)	0.067 (2)
H14	0.4674	0.4928	0.3481	0.081*
C15	0.5425 (9)	0.4225 (6)	0.1788 (7)	0.091 (2)
H15A	0.5404	0.4378	0.0823	0.110*
H15B	0.6677	0.4223	0.2195	0.110*
C16	0.4499 (12)	0.3221 (8)	0.2014 (8)	0.100 (3)
C17	0.2753 (9)	0.3439 (6)	0.2690 (7)	0.0768 (19)
H17	0.3009	0.3385	0.3683	0.092*
C18	0.0718 (10)	0.2130 (6)	0.3117 (10)	0.084 (2)
C19	−0.0681 (10)	0.1408 (6)	0.2474 (8)	0.116 (3)
H19A	−0.0850	0.0864	0.3097	0.174*
H19B	−0.0276	0.1138	0.1650	0.174*
H19C	−0.1813	0.1758	0.2262	0.174*
C20	0.2325 (8)	0.8158 (5)	0.1428 (6)	0.083 (2)
H20A	0.1055	0.7990	0.1384	0.125*
H20B	0.2876	0.7794	0.0732	0.125*
H20C	0.2457	0.8873	0.1288	0.125*
C21	0.1481 (8)	0.4600 (5)	0.0849 (6)	0.083 (2)
H21A	0.2156	0.4187	0.0273	0.125*
H21B	0.1489	0.5290	0.0542	0.125*
H21C	0.0249	0.4361	0.0806	0.125*
O1	0.4948 (9)	0.2388 (5)	0.1678 (7)	0.129 (2)
O2	0.1340 (7)	0.2744 (4)	0.2230 (5)	0.0994 (16)
O3	0.1307 (8)	0.2124 (5)	0.4295 (6)	0.127 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.089 (5)	0.107 (7)	0.075 (5)	0.001 (5)	0.020 (4)	−0.015 (5)
C2	0.122 (7)	0.091 (7)	0.098 (6)	0.004 (5)	0.007 (5)	−0.003 (5)
C3	0.123 (7)	0.094 (7)	0.104 (7)	−0.012 (7)	−0.012 (6)	−0.010 (6)
C4	0.092 (6)	0.108 (7)	0.099 (6)	−0.036 (5)	0.000 (5)	0.003 (5)
C5	0.067 (5)	0.100 (7)	0.083 (5)	−0.012 (4)	0.000 (4)	0.001 (4)
C6	0.057 (4)	0.096 (6)	0.119 (6)	−0.014 (4)	0.016 (4)	0.008 (5)
C7	0.051 (4)	0.103 (6)	0.109 (6)	−0.010 (4)	0.016 (4)	0.003 (5)
C8	0.052 (4)	0.082 (6)	0.064 (4)	−0.001 (4)	−0.005 (3)	0.015 (4)
C9	0.041 (4)	0.102 (6)	0.069 (5)	−0.014 (4)	0.015 (3)	−0.002 (4)
C10	0.057 (4)	0.083 (6)	0.062 (4)	−0.005 (4)	0.001 (4)	−0.001 (4)
C11	0.047 (4)	0.114 (7)	0.091 (6)	−0.010 (4)	0.020 (4)	−0.005 (5)
C12	0.064 (5)	0.125 (7)	0.079 (5)	−0.025 (4)	0.016 (4)	0.011 (5)
C13	0.057 (4)	0.104 (6)	0.054 (4)	−0.014 (4)	0.005 (3)	−0.002 (4)
C14	0.056 (4)	0.090 (6)	0.058 (4)	−0.001 (4)	0.015 (3)	−0.005 (4)
C15	0.067 (5)	0.102 (6)	0.104 (6)	−0.006 (5)	0.005 (4)	0.009 (5)
C16	0.088 (6)	0.109 (8)	0.099 (6)	0.004 (6)	−0.010 (5)	0.012 (7)
C17	0.068 (5)	0.083 (6)	0.077 (5)	−0.018 (5)	−0.003 (4)	0.014 (4)
C18	0.076 (5)	0.083 (6)	0.094 (6)	−0.002 (5)	0.014 (5)	−0.020 (6)
C19	0.088 (6)	0.096 (6)	0.160 (8)	−0.033 (5)	−0.011 (5)	0.000 (5)
C20	0.076 (4)	0.095 (6)	0.077 (5)	0.000 (4)	−0.003 (4)	0.006 (4)
C21	0.075 (4)	0.104 (6)	0.069 (5)	−0.007 (4)	0.001 (4)	0.002 (4)
O1	0.124 (5)	0.096 (5)	0.168 (6)	0.011 (4)	0.022 (4)	0.013 (4)
O2	0.107 (4)	0.100 (4)	0.087 (4)	−0.037 (3)	−0.008 (3)	0.020 (3)
O3	0.141 (5)	0.142 (5)	0.100 (4)	−0.057 (4)	0.027 (4)	0.001 (4)

Geometric parameters (Å, º) top

C1—C2	1.497 (11)	C11—H11B	0.9700
C1—C10	1.536 (8)	C12—C13	1.534 (8)
C1—H1A	0.9700	C12—H12A	0.9700
C1—H1B	0.9700	C12—H12B	0.9700
C2—C3	1.331 (10)	C13—C21	1.512 (8)
C2—H2	0.9300	C13—C17	1.522 (9)
C3—C4	1.473 (10)	C13—C14	1.534 (8)
C3—H3	0.9300	C14—C15	1.524 (9)
C4—C5	1.544 (10)	C14—H14	0.9800
C4—H4A	0.9700	C15—C16	1.517 (11)
C4—H4B	0.9700	C15—H15A	0.9700
C5—C6	1.533 (8)	C15—H15B	0.9700
C5—C10	1.538 (8)	C16—O1	1.204 (9)
C5—H5	0.9800	C16—C17	1.536 (10)
C6—C7	1.528 (9)	C17—O2	1.429 (7)
C6—H6A	0.9700	C17—H17	0.9800
C6—H6B	0.9700	C18—O3	1.197 (8)
C7—C8	1.525 (8)	C18—O2	1.306 (9)
C7—H7A	0.9700	C18—C19	1.500 (9)
C7—H7B	0.9700	C19—H19A	0.9600
C8—C14	1.525 (8)	C19—H19B	0.9600
C8—C9	1.568 (8)	C19—H19C	0.9600
C8—H8	0.9800	C20—H20A	0.9600
C9—C10	1.541 (8)	C20—H20B	0.9600
C9—C11	1.549 (7)	C20—H20C	0.9600
C9—H9	0.9800	C21—H21A	0.9600
C10—C20	1.543 (8)	C21—H21B	0.9600
C11—C12	1.536 (9)	C21—H21C	0.9600
C11—H11A	0.9700

C2—C1—C10	114.4 (7)	C9—C11—H11B	108.8
C2—C1—H1A	108.7	H11A—C11—H11B	107.7
C10—C1—H1A	108.7	C13—C12—C11	111.2 (5)
C2—C1—H1B	108.7	C13—C12—H12A	109.4
C10—C1—H1B	108.7	C11—C12—H12A	109.4
H1A—C1—H1B	107.6	C13—C12—H12B	109.4
C3—C2—C1	122.2 (8)	C11—C12—H12B	109.4
C3—C2—H2	118.9	H12A—C12—H12B	108.0
C1—C2—H2	118.9	C21—C13—C17	110.0 (5)
C2—C3—C4	122.8 (8)	C21—C13—C12	111.4 (5)
C2—C3—H3	118.6	C17—C13—C12	115.2 (6)
C4—C3—H3	118.6	C21—C13—C14	113.6 (5)
C3—C4—C5	113.9 (7)	C17—C13—C14	99.9 (5)
C3—C4—H4A	108.8	C12—C13—C14	106.3 (5)
C5—C4—H4A	108.8	C15—C14—C8	118.2 (5)
C3—C4—H4B	108.8	C15—C14—C13	104.2 (5)
C5—C4—H4B	108.8	C8—C14—C13	114.3 (6)
H4A—C4—H4B	107.7	C15—C14—H14	106.4
C6—C5—C10	113.7 (6)	C8—C14—H14	106.4
C6—C5—C4	110.7 (6)	C13—C14—H14	106.4
C10—C5—C4	111.2 (6)	C16—C15—C14	102.9 (6)
C6—C5—H5	106.9	C16—C15—H15A	111.2
C10—C5—H5	106.9	C14—C15—H15A	111.2
C4—C5—H5	106.9	C16—C15—H15B	111.2
C7—C6—C5	110.6 (6)	C14—C15—H15B	111.2
C7—C6—H6A	109.5	H15A—C15—H15B	109.1
C5—C6—H6A	109.5	O1—C16—C15	128.1 (8)
C7—C6—H6B	109.5	O1—C16—C17	123.8 (9)
C5—C6—H6B	109.5	C15—C16—C17	108.1 (8)
H6A—C6—H6B	108.1	O2—C17—C13	114.5 (5)
C8—C7—C6	111.8 (6)	O2—C17—C16	111.1 (6)
C8—C7—H7A	109.3	C13—C17—C16	102.9 (6)
C6—C7—H7A	109.3	O2—C17—H17	109.4
C8—C7—H7B	109.3	C13—C17—H17	109.4
C6—C7—H7B	109.3	C16—C17—H17	109.4
H7A—C7—H7B	107.9	O3—C18—O2	122.2 (8)
C14—C8—C7	111.6 (5)	O3—C18—C19	125.0 (9)
C14—C8—C9	108.0 (5)	O2—C18—C19	112.7 (8)
C7—C8—C9	109.8 (5)	C18—C19—H19A	109.5
C14—C8—H8	109.1	C18—C19—H19B	109.5
C7—C8—H8	109.1	H19A—C19—H19B	109.5
C9—C8—H8	109.1	C18—C19—H19C	109.5
C10—C9—C11	113.7 (6)	H19A—C19—H19C	109.5
C10—C9—C8	113.3 (5)	H19B—C19—H19C	109.5
C11—C9—C8	109.9 (5)	C10—C20—H20A	109.5
C10—C9—H9	106.5	C10—C20—H20B	109.5
C11—C9—H9	106.5	H20A—C20—H20B	109.5
C8—C9—H9	106.5	C10—C20—H20C	109.5
C1—C10—C5	106.3 (6)	H20A—C20—H20C	109.5
C1—C10—C9	109.5 (6)	H20B—C20—H20C	109.5
C5—C10—C9	107.1 (5)	C13—C21—H21A	109.5
C1—C10—C20	110.1 (5)	C13—C21—H21B	109.5
C5—C10—C20	111.7 (5)	H21A—C21—H21B	109.5
C9—C10—C20	112.0 (5)	C13—C21—H21C	109.5
C12—C11—C9	113.6 (6)	H21A—C21—H21C	109.5
C12—C11—H11A	108.8	H21B—C21—H21C	109.5
C9—C11—H11A	108.8	C18—O2—C17	118.7 (6)
C12—C11—H11B	108.8

C10—C1—C2—C3	−19.1 (10)	C11—C12—C13—C21	−67.3 (7)
C1—C2—C3—C4	−1.9 (13)	C11—C12—C13—C17	166.6 (5)
C2—C3—C4—C5	−10.3 (11)	C11—C12—C13—C14	57.0 (7)
C3—C4—C5—C6	170.4 (6)	C7—C8—C14—C15	−54.7 (8)
C3—C4—C5—C10	43.0 (8)	C9—C8—C14—C15	−175.5 (5)
C10—C5—C6—C7	−57.3 (8)	C7—C8—C14—C13	−177.9 (5)
C4—C5—C6—C7	176.7 (6)	C9—C8—C14—C13	61.3 (6)
C5—C6—C7—C8	55.4 (8)	C21—C13—C14—C15	−70.3 (7)
C6—C7—C8—C14	−174.4 (6)	C17—C13—C14—C15	46.7 (6)
C6—C7—C8—C9	−54.7 (7)	C12—C13—C14—C15	166.8 (5)
C14—C8—C9—C10	178.5 (5)	C21—C13—C14—C8	60.2 (7)
C7—C8—C9—C10	56.5 (7)	C17—C13—C14—C8	177.3 (5)
C14—C8—C9—C11	−53.2 (7)	C12—C13—C14—C8	−62.7 (7)
C7—C8—C9—C11	−175.1 (6)	C8—C14—C15—C16	−161.0 (5)
C2—C1—C10—C5	49.1 (8)	C13—C14—C15—C16	−32.9 (7)
C2—C1—C10—C9	164.4 (6)	C14—C15—C16—O1	−177.1 (9)
C2—C1—C10—C20	−72.0 (7)	C14—C15—C16—C17	6.5 (7)
C6—C5—C10—C1	173.3 (7)	C21—C13—C17—O2	−42.2 (7)
C4—C5—C10—C1	−60.9 (7)	C12—C13—C17—O2	84.6 (6)
C6—C5—C10—C9	56.3 (7)	C14—C13—C17—O2	−162.0 (5)
C4—C5—C10—C9	−177.9 (5)	C21—C13—C17—C16	78.5 (6)
C6—C5—C10—C20	−66.6 (8)	C12—C13—C17—C16	−154.6 (6)
C4—C5—C10—C20	59.2 (8)	C14—C13—C17—C16	−41.3 (6)
C11—C9—C10—C1	63.0 (6)	O1—C16—C17—O2	−31.4 (11)
C8—C9—C10—C1	−170.6 (5)	C15—C16—C17—O2	145.2 (6)
C11—C9—C10—C5	177.9 (5)	O1—C16—C17—C13	−154.4 (8)
C8—C9—C10—C5	−55.7 (6)	C15—C16—C17—C13	22.2 (7)
C11—C9—C10—C20	−59.4 (7)	O3—C18—O2—C17	−0.9 (11)
C8—C9—C10—C20	67.0 (6)	C19—C18—O2—C17	−176.8 (6)
C10—C9—C11—C12	−178.9 (6)	C13—C17—O2—C18	−127.4 (6)
C8—C9—C11—C12	53.0 (7)	C16—C17—O2—C18	116.5 (7)
C9—C11—C12—C13	−56.0 (7)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₃₀O₃
M_r	330.45
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	7.383 (5), 13.200 (9), 9.843 (7)
β (°)	95.687 (10)
V (Å³)	954.5 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.40 × 0.32

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5527, 1794, 864
R_int	0.102
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.136, 0.86
No. of reflections	1794
No. of parameters	221
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.11

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x−1, y, z.

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. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Newaz, S. N. & Tcholakian, R. K. (1984). Steroids, 43, 445–456. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tuba, Z. (1980). Arzneim. Forschung. 30, 342–346. CAS Google Scholar
Tuba, Z., Maho, S. & Vizi, S. (2002). Curr. Med. Chem. 9, 1507–1536. Web of Science CrossRef PubMed CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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