(4aS,4bR,7R,10aS)-3,7-Dimethyl-10a-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-deca­hydro­phenanthrene-1,4-dione

Caracelli, I.; Zukerman-Schpector, J.; Machado, A.T.L.; Brocksom, T.J.; Ferreira, M.L.; Tiekink, E.R.T.

doi:10.1107/S160053681104517X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3192

https://doi.org/10.1107/S160053681104517X

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(4aS,4bR,7R,10aS)-3,7-Dimethyl-10a-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-decahydrophenanthrene-1,4-dione

Ignez Caracelli,^a ^* Julio Zukerman-Schpector,^b André T. Lousada Machado,^b Timothy J. Brocksom,^c M. Lúcia Ferreira ^c and Edward R. T. Tiekink ^d

^aBioMat-Departamento de Física, Universidade Federal de São Carlos, CP 676, 13565-905 São Carlos, SP, Brazil, ^bLaboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Universidade Federal de São Carlos, Departamento de Química, CP 676, 13565-905 São Carlos, SP, Brazil, ^cUniversidade Federal de São Carlos, Departamento de Química, CP 676, 13565-905 São Carlos, SP, Brazil, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: ignez@ufscar.br

(Received 24 October 2011; accepted 27 October 2011; online 5 November 2011)

In the title compound, C₁₉H₂₆O₂, the A ring adopts a chair conformation, whereas the B and C rings both adopt distorted half-chair conformations with the quaternary C atom common to both rings lying 0.577 (3) and 0.648 (3) Å out of the approximate plane defined by the remaining five C atoms (r.m.s. deviations = 0.1386 and 0.1156 Å) for the B and C rings, respectively. Molecules are assembled in the crystal through C—H⋯O interactions involving both carbonyl O atoms, which lead to supramolecular chains aligned along the b axis.

Related literature

For background to the biological activity of some diterpene compounds, see: Guo et al. (2011 ); Slusarczyk et al. (2011 ). For the synthesis, see: Ferreira (2002 ). For conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₉H₂₆O₂
M_r = 286.40
Monoclinic, P 2₁
a = 10.882 (1) Å
b = 6.6015 (9) Å
c = 11.656 (1) Å
β = 102.53 (2)°
V = 817.40 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 290 K
0.15 × 0.10 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 Mach 3 diffractometer
2470 measured reflections
2334 independent reflections
1100 reflections with I > 2σ(I)
R_int = 0.045
3 standard reflections every 30 min intensity decay: 1.4%

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.122
S = 0.98
2334 reflections
191 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.98	2.50	3.443 (3)	161
C5—H5⋯O1ⁱⁱ	0.93	2.52	3.438 (4)	171
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990 ); program(s) used to solve structure: SIR92 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ), DIAMOND (Brandenburg, 2006 ) and MarvinSketch (Chemaxon, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681104517X/hg5119sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104517X/hg5119Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681104517X/hg5119Isup3.cml

checkCIF report

Comment top

Natural diterpenes exhibit a wide range of biological activities such as neuroprotectives (Guo et al. 2011) and as antiplasmodials and antitrypanocidals (Slusarczyk et al. 2011). While aiming at the synthesis of some hydrophenanthrene diterpenes, a series of new intermediates were obtained and among them, was the title compound (Ferreira, 2002), (I), which has been characterized crystallographically.

In (I), Fig. 1, a chair conformation is found for ring A. Each of the B and C rings presents a distorted half-chair conformation, with the C7 atom, common to both rings, lying 0.5769 (26) and 0.6480 (28) Å, respectively, out of the approximate plane defined by the remaining five C atoms (r.m.s. deviation = 0.1386 and 0.1156 Å for B and C, respectively). The ring puckering parameters for the three rings are: q₂ = 0.022 (3), 0.315 (3), 0.384 (3) Å, q₃ = 0.563 (3), -0.273 (3), -0.282 (3) Å, QT = 0.563 (3), 0.417 (3), 0.477 (3) Å, and θ = 2.3 (3), 130.9 (4), 126.3 (4)°, for rings A, B and C, respectively (Cremer & Pople, 1975).

In the crystal packing, the molecules are linked through C–H···O interactions, Table 1, involving both carbonyl-O atoms. This results in the formation of a supramolecular chain along the b axis, Fig. 2. The chains pack in the crystal structure with no specific interactions between them, Fig. 3.

Related literature top

For background to the biological activity of some diterpene compounds, see: Guo et al. (2011); Slusarczyk et al. (2011). For the synthesis, see: Ferreira (2002). For conformational analysis, see: Cremer & Pople (1975).

Experimental top

The detailed synthesis of the title compound is described in a Ph.D. thesis (Ferreira, 2002). Crystals were grown by slow evaporation from its methanol solution held at 293 K; M.pt: 429.6–432.2 K. ¹H-NMR (CDCl₃, 400 MHz): δ (p.p.m.) 6.52 (q, 1H, J = 1.5 Hz); 5.35 (d, 1H, J = 3.9 Hz); 3.36 (d, 1H, J = 7.7 Hz); 2.65 (m, 1H); 2.35–2.38 (m, 2H); 2.18–2.19 (m, 2H); 2.01–2.06 (m, 1H); 1.96 (d, 3H, J = 1.5 Hz); 1.90–1.20 (m, 1H); 1.42–1.51 (m, 2H); 1.17–1.27 (m, 2H); 0.94 (d, 3H, J = 6.8 Hz); 0.75 (d, 3H, J = 5.8 Hz); 0.69 (d, 3H, J = 6.8 Hz); ¹³C (CDCl₃, 100 MHz) δ (p.p.m.) 203.2; 202.6; 149.4; 136.5; 134.3; 118.7; 54.5; 54.2; 42.4; 41.2; 35.9; 32.9; 29.5; 28.0; 21.5; 17.6; 17.4; 16.9; 15.5. Analysis found: C 79.42, H 9.17%. C₁₉H₂₆O₂ requires: C 79.68, H 9.15%.

Structure description top

For background to the biological activity of some diterpene compounds, see: Guo et al. (2011); Slusarczyk et al. (2011). For the synthesis, see: Ferreira (2002). For conformational analysis, see: Cremer & Pople (1975).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and MarvinSketch (Chemaxon, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of compound (I) showing atom labelling scheme and displacement ellipsoids at the 30% probability level (arbitrary spheres for the H atoms).
	Fig. 2. A view of the supramolecular chain in (I) aligned along the b axis and sustained by C—H···O interactions shown as orange dashed lines.
	Fig. 3. A view in projection down the b axis of the unit-cell contents of (I).

(4aS,4bR,7R,10aS)-3,7-Dimethyl- 10a-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-decahydrophenanthrene-1,4-dione top

Crystal data top

C₁₉H₂₆O₂	F(000) = 312
M_r = 286.40	D_x = 1.164 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 10.882 (1) Å	θ = 10.3–18.3°
b = 6.6015 (9) Å	µ = 0.07 mm⁻¹
c = 11.656 (1) Å	T = 290 K
β = 102.53 (2)°	Irregular, colourless
V = 817.40 (16) Å³	0.15 × 0.10 × 0.08 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 Mach 3 diffractometer	R_int = 0.045
Radiation source: fine-focus sealed tube	θ_max = 29.0°, θ_min = 1.8°
Graphite monochromator	h = −14→14
ω/–2θ scans	k = 0→8
2470 measured reflections	l = 0→15
2334 independent reflections	3 standard reflections every 30 min
1100 reflections with I > 2σ(I)	intensity decay: 1.4%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.058P)²] where P = (F_o² + 2F_c²)/3
2334 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₉H₂₆O₂	V = 817.40 (16) Å³
M_r = 286.40	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.882 (1) Å	µ = 0.07 mm⁻¹
b = 6.6015 (9) Å	T = 290 K
c = 11.656 (1) Å	0.15 × 0.10 × 0.08 mm
β = 102.53 (2)°

Data collection top

Enraf–Nonius CAD-4 Mach 3 diffractometer	R_int = 0.045
2470 measured reflections	3 standard reflections every 30 min
2334 independent reflections	intensity decay: 1.4%
1100 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.122	H-atom parameters constrained
S = 0.98	Δρ_max = 0.18 e Å⁻³
2334 reflections	Δρ_min = −0.18 e Å⁻³
191 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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	0.0639 (2)	0.5986 (4)	0.7953 (2)	0.0384 (6)
H1	0.0437	0.4610	0.8167	0.046*
C2	0.2045 (2)	0.5917 (4)	0.7858 (2)	0.0343 (6)
H2	0.2203	0.4553	0.7591	0.041*
C3	0.2885 (2)	0.6188 (4)	0.9059 (2)	0.0370 (6)
C4	0.3242 (2)	0.8281 (5)	0.9474 (3)	0.0410 (7)
C5	0.2941 (3)	0.9818 (5)	0.8724 (2)	0.0432 (7)
H5	0.3120	1.1128	0.9005	0.052*
C6	0.2337 (3)	0.9551 (4)	0.7467 (2)	0.0415 (7)
C7	0.2397 (3)	0.7433 (4)	0.6959 (2)	0.0372 (7)
C8	0.1491 (3)	0.7223 (5)	0.5767 (2)	0.0471 (7)
H8A	0.1565	0.8416	0.5300	0.057*
H8B	0.1741	0.6062	0.5361	0.057*
C9	0.0148 (3)	0.6975 (5)	0.5837 (2)	0.0467 (7)
H9	−0.0461	0.7233	0.5159	0.056*
C10	−0.0248 (2)	0.6416 (4)	0.6784 (2)	0.0422 (7)
C11	−0.1614 (3)	0.6269 (6)	0.6815 (3)	0.0566 (8)
H11A	−0.1813	0.4878	0.6972	0.068*
H11B	−0.2119	0.6641	0.6052	0.068*
C12	−0.1952 (3)	0.7642 (6)	0.7752 (3)	0.0559 (9)
H12	−0.2815	0.7323	0.7813	0.067*
C13	−0.1084 (3)	0.7170 (6)	0.8930 (3)	0.0537 (8)
H13A	−0.1243	0.5799	0.9159	0.064*
H13B	−0.1274	0.8083	0.9520	0.064*
C14	0.0305 (2)	0.7376 (5)	0.8899 (2)	0.0437 (7)
H14A	0.0819	0.7022	0.9661	0.052*
H14B	0.0485	0.8771	0.8733	0.052*
C15	0.3875 (3)	0.8537 (6)	1.0739 (2)	0.0571 (9)
H15A	0.4098	0.9934	1.0890	0.086*
H15B	0.4621	0.7718	1.0914	0.086*
H15C	0.3311	0.8124	1.1225	0.086*
C16	0.3807 (3)	0.7097 (5)	0.6859 (2)	0.0479 (7)
H16	0.4338	0.7277	0.7647	0.057*
C17	0.4060 (3)	0.4981 (6)	0.6445 (3)	0.0711 (11)
H17A	0.3798	0.3992	0.6947	0.107*
H17B	0.4943	0.4827	0.6475	0.107*
H17C	0.3597	0.4788	0.5653	0.107*
C18	0.4232 (4)	0.8654 (8)	0.6055 (4)	0.0969 (16)
H18A	0.4079	0.9995	0.6311	0.145*
H18B	0.3769	0.8457	0.5263	0.145*
H18C	0.5115	0.8488	0.6086	0.145*
C19	−0.1910 (4)	0.9882 (7)	0.7419 (3)	0.0748 (11)
H19A	−0.2468	1.0110	0.6671	0.112*
H19B	−0.1068	1.0240	0.7372	0.112*
H19C	−0.2169	1.0700	0.8005	0.112*
O1	0.32371 (19)	0.4746 (3)	0.96994 (17)	0.0523 (6)
O2	0.1854 (2)	1.0979 (3)	0.6885 (2)	0.0685 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0447 (15)	0.0296 (14)	0.0405 (14)	−0.0061 (13)	0.0087 (11)	0.0004 (13)
C2	0.0455 (15)	0.0231 (14)	0.0352 (13)	0.0008 (13)	0.0106 (12)	−0.0005 (12)
C3	0.0402 (15)	0.0341 (16)	0.0387 (14)	0.0034 (13)	0.0130 (12)	0.0045 (14)
C4	0.0362 (13)	0.0428 (18)	0.0443 (16)	−0.0067 (13)	0.0093 (12)	−0.0088 (15)
C5	0.0481 (16)	0.0291 (15)	0.0515 (16)	−0.0075 (15)	0.0089 (13)	−0.0057 (16)
C6	0.0456 (15)	0.0309 (16)	0.0481 (17)	−0.0071 (14)	0.0100 (13)	0.0028 (15)
C7	0.0477 (15)	0.0298 (16)	0.0355 (14)	−0.0007 (13)	0.0121 (12)	0.0008 (12)
C8	0.0636 (19)	0.0435 (18)	0.0357 (14)	0.0031 (16)	0.0135 (13)	0.0008 (14)
C9	0.0567 (18)	0.0395 (17)	0.0395 (15)	−0.0014 (14)	0.0005 (14)	−0.0069 (14)
C10	0.0456 (16)	0.0366 (17)	0.0421 (15)	−0.0070 (13)	0.0041 (12)	−0.0100 (13)
C11	0.0468 (17)	0.061 (2)	0.0570 (18)	−0.0093 (17)	0.0007 (14)	0.0006 (18)
C12	0.0418 (15)	0.069 (2)	0.0583 (19)	−0.0028 (16)	0.0130 (14)	0.0004 (18)
C13	0.0484 (17)	0.064 (2)	0.0515 (17)	0.0008 (17)	0.0178 (13)	0.0047 (17)
C14	0.0427 (15)	0.0497 (19)	0.0393 (15)	−0.0011 (14)	0.0103 (12)	−0.0004 (14)
C15	0.0494 (17)	0.070 (2)	0.0501 (18)	−0.0090 (18)	0.0060 (14)	−0.0125 (18)
C16	0.0486 (17)	0.0531 (19)	0.0451 (15)	0.0001 (16)	0.0170 (13)	0.0074 (16)
C17	0.076 (2)	0.073 (3)	0.070 (2)	0.021 (2)	0.0293 (18)	−0.007 (2)
C18	0.081 (3)	0.098 (4)	0.127 (4)	0.004 (3)	0.058 (3)	0.046 (3)
C19	0.079 (2)	0.073 (3)	0.075 (2)	0.020 (2)	0.0200 (19)	0.003 (2)
O1	0.0620 (13)	0.0425 (13)	0.0506 (12)	0.0052 (11)	0.0081 (10)	0.0102 (11)
O2	0.0952 (18)	0.0276 (12)	0.0723 (15)	0.0052 (13)	−0.0047 (13)	0.0091 (12)

Geometric parameters (Å, º) top

C1—C10	1.515 (4)	C11—H11B	0.9700
C1—C14	1.538 (4)	C12—C13	1.521 (4)
C1—C2	1.559 (3)	C12—C19	1.532 (6)
C1—H1	0.9800	C12—H12	0.9800
C2—C3	1.507 (4)	C13—C14	1.526 (4)
C2—C7	1.556 (3)	C13—H13A	0.9700
C2—H2	0.9800	C13—H13B	0.9700
C3—O1	1.219 (3)	C14—H14A	0.9700
C3—C4	1.488 (4)	C14—H14B	0.9700
C4—C5	1.333 (4)	C15—H15A	0.9600
C4—C15	1.495 (4)	C15—H15B	0.9600
C5—C6	1.480 (4)	C15—H15C	0.9600
C5—H5	0.9300	C16—C17	1.522 (5)
C6—O2	1.213 (4)	C16—C18	1.528 (5)
C6—C7	1.526 (4)	C16—H16	0.9800
C7—C8	1.525 (4)	C17—H17A	0.9600
C7—C16	1.580 (4)	C17—H17B	0.9600
C8—C9	1.491 (4)	C17—H17C	0.9600
C8—H8A	0.9700	C18—H18A	0.9600
C8—H8B	0.9700	C18—H18B	0.9600
C9—C10	1.322 (4)	C18—H18C	0.9600
C9—H9	0.9300	C19—H19A	0.9600
C10—C11	1.498 (4)	C19—H19B	0.9600
C11—C12	1.524 (5)	C19—H19C	0.9600
C11—H11A	0.9700

C10—C1—C14	109.2 (2)	C13—C12—C11	109.0 (3)
C10—C1—C2	112.7 (2)	C13—C12—C19	112.3 (3)
C14—C1—C2	117.2 (2)	C11—C12—C19	111.6 (3)
C10—C1—H1	105.6	C13—C12—H12	107.9
C14—C1—H1	105.6	C11—C12—H12	107.9
C2—C1—H1	105.6	C19—C12—H12	107.9
C3—C2—C7	111.2 (2)	C12—C13—C14	112.6 (2)
C3—C2—C1	109.7 (2)	C12—C13—H13A	109.1
C7—C2—C1	114.7 (2)	C14—C13—H13A	109.1
C3—C2—H2	106.9	C12—C13—H13B	109.1
C7—C2—H2	106.9	C14—C13—H13B	109.1
C1—C2—H2	106.9	H13A—C13—H13B	107.8
O1—C3—C4	120.0 (2)	C13—C14—C1	110.7 (2)
O1—C3—C2	121.5 (3)	C13—C14—H14A	109.5
C4—C3—C2	118.4 (2)	C1—C14—H14A	109.5
C5—C4—C3	118.9 (2)	C13—C14—H14B	109.5
C5—C4—C15	123.8 (3)	C1—C14—H14B	109.5
C3—C4—C15	117.2 (3)	H14A—C14—H14B	108.1
C4—C5—C6	123.5 (3)	C4—C15—H15A	109.5
C4—C5—H5	118.3	C4—C15—H15B	109.5
C6—C5—H5	118.3	H15A—C15—H15B	109.5
O2—C6—C5	120.4 (3)	C4—C15—H15C	109.5
O2—C6—C7	123.0 (2)	H15A—C15—H15C	109.5
C5—C6—C7	116.5 (2)	H15B—C15—H15C	109.5
C8—C7—C6	111.3 (2)	C17—C16—C18	108.9 (3)
C8—C7—C2	110.5 (2)	C17—C16—C7	113.4 (3)
C6—C7—C2	106.9 (2)	C18—C16—C7	112.3 (3)
C8—C7—C16	111.5 (2)	C17—C16—H16	107.3
C6—C7—C16	106.3 (2)	C18—C16—H16	107.3
C2—C7—C16	110.1 (2)	C7—C16—H16	107.3
C9—C8—C7	114.1 (2)	C16—C17—H17A	109.5
C9—C8—H8A	108.7	C16—C17—H17B	109.5
C7—C8—H8A	108.7	H17A—C17—H17B	109.5
C9—C8—H8B	108.7	C16—C17—H17C	109.5
C7—C8—H8B	108.7	H17A—C17—H17C	109.5
H8A—C8—H8B	107.6	H17B—C17—H17C	109.5
C10—C9—C8	125.3 (3)	C16—C18—H18A	109.5
C10—C9—H9	117.4	C16—C18—H18B	109.5
C8—C9—H9	117.4	H18A—C18—H18B	109.5
C9—C10—C11	122.9 (3)	C16—C18—H18C	109.5
C9—C10—C1	122.9 (2)	H18A—C18—H18C	109.5
C11—C10—C1	114.1 (2)	H18B—C18—H18C	109.5
C10—C11—C12	111.9 (3)	C12—C19—H19A	109.5
C10—C11—H11A	109.2	C12—C19—H19B	109.5
C12—C11—H11A	109.2	H19A—C19—H19B	109.5
C10—C11—H11B	109.2	C12—C19—H19C	109.5
C12—C11—H11B	109.2	H19A—C19—H19C	109.5
H11A—C11—H11B	107.9	H19B—C19—H19C	109.5

C10—C1—C2—C3	161.1 (2)	C1—C2—C7—C16	−175.1 (2)
C14—C1—C2—C3	33.1 (3)	C6—C7—C8—C9	−76.9 (3)
C10—C1—C2—C7	35.2 (3)	C2—C7—C8—C9	41.7 (3)
C14—C1—C2—C7	−92.8 (3)	C16—C7—C8—C9	164.6 (2)
C7—C2—C3—O1	−143.0 (3)	C7—C8—C9—C10	−18.3 (4)
C1—C2—C3—O1	89.0 (3)	C8—C9—C10—C11	177.6 (3)
C7—C2—C3—C4	39.3 (3)	C8—C9—C10—C1	1.2 (5)
C1—C2—C3—C4	−88.6 (3)	C14—C1—C10—C9	122.4 (3)
O1—C3—C4—C5	174.1 (3)	C2—C1—C10—C9	−9.7 (4)
C2—C3—C4—C5	−8.2 (4)	C14—C1—C10—C11	−54.3 (3)
O1—C3—C4—C15	−8.5 (4)	C2—C1—C10—C11	173.6 (2)
C2—C3—C4—C15	169.2 (2)	C9—C10—C11—C12	−121.1 (3)
C3—C4—C5—C6	−4.0 (4)	C1—C10—C11—C12	55.6 (4)
C15—C4—C5—C6	178.8 (3)	C10—C11—C12—C13	−54.3 (4)
C4—C5—C6—O2	164.9 (3)	C10—C11—C12—C19	70.3 (4)
C4—C5—C6—C7	−16.9 (4)	C11—C12—C13—C14	56.3 (4)
O2—C6—C7—C8	−15.4 (4)	C19—C12—C13—C14	−67.8 (4)
C5—C6—C7—C8	166.5 (2)	C12—C13—C14—C1	−57.5 (4)
O2—C6—C7—C2	−136.2 (3)	C10—C1—C14—C13	54.0 (3)
C5—C6—C7—C2	45.7 (3)	C2—C1—C14—C13	−176.3 (2)
O2—C6—C7—C16	106.2 (3)	C8—C7—C16—C17	−62.7 (3)
C5—C6—C7—C16	−72.0 (3)	C6—C7—C16—C17	175.8 (2)
C3—C2—C7—C8	−176.7 (2)	C2—C7—C16—C17	60.4 (3)
C1—C2—C7—C8	−51.5 (3)	C8—C7—C16—C18	61.2 (4)
C3—C2—C7—C6	−55.4 (3)	C6—C7—C16—C18	−60.3 (3)
C1—C2—C7—C6	69.8 (3)	C2—C7—C16—C18	−175.7 (3)
C3—C2—C7—C16	59.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.98	2.50	3.443 (3)	161
C5—H5···O1ⁱⁱ	0.93	2.52	3.438 (4)	171

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₆O₂
M_r	286.40
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	290
a, b, c (Å)	10.882 (1), 6.6015 (9), 11.656 (1)
β (°)	102.53 (2)
V (Å³)	817.40 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.15 × 0.10 × 0.08

Data collection
Diffractometer	Enraf–Nonius CAD-4 Mach 3
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2470, 2334, 1100
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.681

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.122, 0.98
No. of reflections	2334
No. of parameters	191
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), MolEN (Fair, 1990), SIR92 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and MarvinSketch (Chemaxon, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.98	2.50	3.443 (3)	161
C5—H5···O1ⁱⁱ	0.93	2.52	3.438 (4)	171

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z.

Acknowledgements

We thank FAPESP, CNPq (306532/2009–3 to JZ-S; 308116/2010–0 to IC) and CAPES (808/2009 to JZ-S and IC) for financial support.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Chemaxon (2009). MarvinSketch. www.chemaxon.com. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Fair, C. K. (1990). MolEN. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Ferreira, M. L. (2002). PhD thesis, Universidade Federal de São Carlos, Brazil. Google Scholar
Guo, P., Li, Y., Xu, J., Guo, Y., Jin, D.-Q., Gao, J., Hou, W. & Zhang, T. (2011). Fitoterapia, 82, 1123–1127. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Slusarczyk, S., Zimmermann, S., Kaiser, M., Matkowski, A., Hamburger, M. & Adams, M. (2011). Planta Med. 77, 1594–1596. Web of Science CAS PubMed Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

(4aS,4bR,7R,10aS)-3,7-Di­methyl-10a-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-deca­hydro­phenanthrene-1,4-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(4aS,4bR,7R,10aS)-3,7-Dimethyl-10a-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-decahydrophenanthrene-1,4-dione