(4R*,4aS*,4bS*,5R*,10aR*)-4-Hy­droxy-4a,5-dimethyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-deca­hydro­phenan­thren-1-one

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

doi:10.1107/S1600536811048008

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3338

https://doi.org/10.1107/S1600536811048008

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(4R,4aS,4bS,5R,10aR*)-4-Hydroxy-4a,5-dimethyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-decahydrophenanthren-1-one

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

(Received 26 October 2011; accepted 11 November 2011; online 16 November 2011)

In the title compound, C₁₉H₂₈O₂, the A ring adopts a chair conformation. Both the B and C rings adopt envelope conformations with the C atoms common to both rings and adjacent to the carbonyl and hydroxyl groups, respectively, lying 0.604 (3) and 0.634 (3) Å out of the mean planes defined by the remaining five C atoms of rings B and C, respectively (r.m.s. deviations = 0.0100 and 0.0157 Å, respectively). The formation of linear supramolecular C(7) chains along the a axis mediated by hydroxy-O—H⋯O(carbonyl) hydrogen bonds is the most prominent feature of the crystal packing.

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

C₁₉H₂₈O₂
M_r = 288.41
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.5507 (9) Å
b = 11.733 (1) Å
c = 22.338 (3) Å
V = 1716.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 290 K
0.15 × 0.12 × 0.09 mm

Data collection

Enraf–Nonius CAD-4 Mach 3 diffractometer
2272 measured reflections
1945 independent reflections
1077 reflections with I > 2σ(I)
R_int = 0.038
3 standard reflections every 30 min intensity decay: 2.0%

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.122
S = 1.02
1945 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.15 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
O2—H2o⋯O1ⁱ	0.82	2.02	2.804 (3)	160
Symmetry code: (i) x-1, y, 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/S1600536811048008/hb6477sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048008/hb6477Isup2.hkl

checkCIF report

Comment top

Natural diterpenes exhibit a wide range of biological activities such as neuroprotectives (Guo et al., 2011) and as anti-plasmodials and anti-trypanocidals (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.

The A ring in (I), Fig. 1, has a chair conformation. Each of the B and C rings presents a half-chair conformation with atom C7 lying 0.604 (3) Å and C2 lying 0.634 (3) Å out of the approximate plane defined by the remaining five C atoms of rings B and C, respectively (r.m.s. deviation 0.0100 and 0.0157 Å for rings B and C, respectively). The ring puckering parameters are: q₂ = 0.040 (4), 0.348 (3), 0.367 (3) Å; q₃ = 0.530 (4), 0.265 (3), 0.269 (3) Å; QT = 0.531 (4), 0.438 (3), 0.455 (3) Å; and θ = 3.9 (4), 52.7 (4), 53.7 (4)°, for rings A, B and C, respectively (Cremer & Pople, 1975).

In the crystal packing, the molecules are linked through O–H···O hydrogen bonds to form linear supramolecular chains along the a axis, Fig. 2 and Table 1. Chains pack in the crystal structure with no specific intermolecular interactions operating 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 hexane solution held at 293 K. ¹H-NMR (CDCl₃, 400 MHz): δ (p.p.m.): 6.47 (d, 1H, J = 5.4 Hz); 5.50 (d, 1H, J = 4.5 Hz); 4.4 (d, 1H, J = 5.4 Hz); 2.87 (heptet, 1H, J = 6.8 Hz); 2.39 (d, 1H, J = 3.7 Hz); 2.29–2.33 (m, 1H); 2.08–2.13 (m, 2H); 1.98–2.03 (m, 2H); 1.68–1.78 (m, 1H); 1.68–1.78 (m, 2H); 1.35 (dt, 2H, J₁ = 12.8 and J₂ = 3.6 Hz); 1.21 (d, 3H, J = 6.5 Hz); 1.16 (s, 3H); 1.06 (d, 3H, J = 6.9 Hz); 1.02 (d, 3H, J = 6.9 Hz); δ(OH) not obs. ¹³C (CDCl₃, 100 MHz) δ (p.p.m.): 202.5; 142.2; 141.8; 136.0; 118.3; 71.0; 53.9; 53.1; 37.6; 36.7; 36.7; 33.6; 29.0; 27.5; 26.1; 26.0; 25.2; 21.4; 21.4 Analysis found: C 78.98, H 9.79%. C₁₉H₂₈O₂ requires: C 79.12, H 9.79%.

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 displacement ellipsoids at the 30% probability level (arbitrary spheres for the H atoms).
	Fig. 2. A view of the linear supramolecular chain along the a axis in (I). The hydroxy-O—H···O(carbonyl) hydrogen bonds are represented by orange dashed lines.
	Fig. 3. A view in projection down the a axis of the unit-cell contents of (I). The hydroxy-O—H···O(carbonyl) hydrogen bonds are represented by orange dashed lines.

(4R*,4aS*,4bS*,5R*,10aR*)-4-Hydroxy-4a,5-dimethyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-decahydrophenanthren-1-one top

Crystal data top

C₁₉H₂₈O₂	F(000) = 632
M_r = 288.41	D_x = 1.116 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 23 reflections
a = 6.5507 (9) Å	θ = 9.1–16.5°
b = 11.733 (1) Å	µ = 0.07 mm⁻¹
c = 22.338 (3) Å	T = 290 K
V = 1716.9 (4) Å³	Irregular, colourless
Z = 4	0.15 × 0.12 × 0.09 mm

Data collection top

Enraf–Nonius CAD-4 Mach 3 diffractometer	R_int = 0.038
Radiation source: fine-focus sealed tube	θ_max = 26.0°, θ_min = 2.0°
Graphite monochromator	h = −1→8
ω/–2θ scans	k = −14→0
2272 measured reflections	l = −27→0
1945 independent reflections	3 standard reflections every 30 min
1077 reflections with I > 2σ(I)	intensity decay: 2.0%

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 = 1.02	w = 1/[σ²(F_o²) + (0.0557P)² + 0.0441P] where P = (F_o² + 2F_c²)/3
1945 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₁₉H₂₈O₂	V = 1716.9 (4) Å³
M_r = 288.41	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.5507 (9) Å	µ = 0.07 mm⁻¹
b = 11.733 (1) Å	T = 290 K
c = 22.338 (3) Å	0.15 × 0.12 × 0.09 mm

Data collection top

Enraf–Nonius CAD-4 Mach 3 diffractometer	R_int = 0.038
2272 measured reflections	3 standard reflections every 30 min
1945 independent reflections	intensity decay: 2.0%
1077 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.02	Δρ_max = 0.15 e Å⁻³
1945 reflections	Δρ_min = −0.11 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	0.5700 (5)	0.1474 (3)	0.87731 (12)	0.0536 (8)
H1	0.6626	0.1974	0.8996	0.064*
C2	0.6209 (4)	0.1683 (2)	0.80946 (13)	0.0488 (8)
C3	0.4355 (4)	0.1501 (3)	0.76804 (12)	0.0478 (7)
H3	0.3371	0.2113	0.7758	0.057*
C4	0.4904 (5)	0.1535 (3)	0.70352 (13)	0.0527 (8)
H4	0.3867	0.1723	0.6769	0.063*
C5	0.6731 (5)	0.1322 (3)	0.68010 (13)	0.0508 (7)
C6	0.8399 (5)	0.1005 (3)	0.72195 (15)	0.0559 (8)
C7	0.7936 (4)	0.0895 (2)	0.78799 (14)	0.0526 (8)
H7	0.9173	0.1121	0.8096	0.063*
C8	0.7588 (5)	−0.0363 (3)	0.80105 (14)	0.0616 (9)
H8A	0.6508	−0.0653	0.7755	0.074*
H8B	0.8823	−0.0789	0.7925	0.074*
C9	0.7016 (6)	−0.0514 (3)	0.86456 (15)	0.0656 (9)
H9	0.7258	−0.1223	0.8818	0.079*
C10	0.6191 (5)	0.0279 (3)	0.89854 (14)	0.0592 (8)
C11	0.5787 (7)	0.0058 (4)	0.96343 (16)	0.0875 (13)
H11A	0.6721	0.0509	0.9874	0.105*
H11B	0.6046	−0.0739	0.9720	0.105*
C12	0.3627 (8)	0.0344 (4)	0.98085 (18)	0.1012 (15)
H12A	0.2688	−0.0165	0.9606	0.121*
H12B	0.3454	0.0245	1.0237	0.121*
C13	0.3167 (8)	0.1551 (3)	0.96402 (16)	0.0900 (12)
H13A	0.4014	0.2053	0.9880	0.108*
H13B	0.1753	0.1712	0.9738	0.108*
C14	0.3521 (6)	0.1821 (3)	0.89755 (16)	0.0699 (10)
H14	0.2546	0.1368	0.8743	0.084*
C15	0.6977 (6)	0.2914 (3)	0.80117 (15)	0.0750 (11)
H15A	0.5933	0.3438	0.8135	0.113*
H15B	0.7300	0.3041	0.7598	0.113*
H15C	0.8177	0.3030	0.8251	0.113*
C16	0.7253 (5)	0.1371 (3)	0.61470 (13)	0.0627 (9)
H16	0.8109	0.0708	0.6056	0.075*
C17	0.8497 (8)	0.2431 (4)	0.60174 (17)	0.1106 (16)
H17A	0.8863	0.2445	0.5601	0.166*
H17B	0.9713	0.2425	0.6257	0.166*
H17C	0.7704	0.3095	0.6111	0.166*
C18	0.5396 (6)	0.1315 (4)	0.57472 (15)	0.0879 (13)
H18A	0.5818	0.1327	0.5336	0.132*
H18B	0.4530	0.1958	0.5826	0.132*
H18C	0.4659	0.0624	0.5826	0.132*
C19	0.2980 (9)	0.3082 (3)	0.88848 (17)	0.1022 (16)
H19A	0.1605	0.3215	0.9015	0.153*
H19B	0.3100	0.3272	0.8468	0.153*
H19C	0.3898	0.3547	0.9114	0.153*
O1	1.0090 (3)	0.0749 (2)	0.70292 (10)	0.0824 (8)
O2	0.3390 (3)	0.04403 (17)	0.78121 (9)	0.0563 (6)
H2o	0.2390	0.0359	0.7595	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0577 (17)	0.0556 (18)	0.0474 (17)	−0.0035 (17)	−0.0097 (15)	−0.0039 (15)
C2	0.0480 (18)	0.0450 (17)	0.0533 (17)	−0.0047 (15)	−0.0104 (15)	0.0007 (13)
C3	0.0434 (16)	0.0470 (17)	0.0529 (17)	0.0061 (15)	−0.0055 (13)	0.0023 (14)
C4	0.0456 (16)	0.0577 (19)	0.0546 (18)	0.0020 (16)	−0.0140 (15)	0.0068 (15)
C5	0.0432 (16)	0.0584 (19)	0.0509 (16)	−0.0044 (16)	−0.0060 (15)	0.0036 (15)
C6	0.0357 (15)	0.068 (2)	0.064 (2)	−0.0068 (16)	−0.0025 (16)	0.0015 (16)
C7	0.0381 (16)	0.0631 (19)	0.0566 (19)	−0.0061 (15)	−0.0127 (15)	0.0056 (16)
C8	0.0565 (18)	0.060 (2)	0.068 (2)	0.0132 (17)	−0.0010 (17)	0.0056 (17)
C9	0.069 (2)	0.057 (2)	0.071 (2)	0.0115 (19)	−0.0020 (18)	0.0172 (17)
C10	0.0614 (19)	0.062 (2)	0.0543 (19)	0.0002 (18)	−0.0080 (17)	0.0110 (17)
C11	0.112 (3)	0.089 (3)	0.062 (2)	−0.001 (3)	0.001 (2)	0.012 (2)
C12	0.127 (4)	0.109 (3)	0.068 (2)	−0.018 (3)	0.028 (3)	0.005 (2)
C13	0.094 (3)	0.108 (3)	0.068 (2)	0.009 (3)	0.014 (2)	−0.017 (2)
C14	0.072 (2)	0.074 (2)	0.064 (2)	0.007 (2)	0.002 (2)	−0.0152 (17)
C15	0.092 (3)	0.054 (2)	0.079 (2)	−0.018 (2)	−0.014 (2)	0.0031 (17)
C16	0.0524 (18)	0.082 (2)	0.0536 (19)	−0.0020 (19)	−0.0015 (16)	0.0041 (17)
C17	0.129 (4)	0.126 (4)	0.077 (3)	−0.042 (4)	0.018 (3)	0.021 (3)
C18	0.077 (2)	0.130 (3)	0.057 (2)	0.019 (3)	−0.017 (2)	−0.009 (2)
C19	0.129 (4)	0.091 (3)	0.087 (3)	0.044 (3)	0.007 (3)	−0.018 (2)
O1	0.0360 (11)	0.143 (2)	0.0685 (15)	0.0035 (15)	0.0004 (12)	0.0002 (15)
O2	0.0438 (11)	0.0629 (13)	0.0623 (13)	−0.0109 (12)	−0.0077 (11)	−0.0014 (11)

Geometric parameters (Å, º) top

C1—C10	1.514 (4)	C11—H11B	0.9700
C1—C14	1.552 (5)	C12—C13	1.495 (6)
C1—C2	1.571 (4)	C12—H12A	0.9700
C1—H1	0.9800	C12—H12B	0.9700
C2—C7	1.538 (4)	C13—C14	1.536 (5)
C2—C15	1.541 (4)	C13—H13A	0.9700
C2—C3	1.542 (4)	C13—H13B	0.9700
C3—O2	1.427 (3)	C14—C19	1.535 (5)
C3—C4	1.486 (4)	C14—H14	0.9800
C3—H3	0.9800	C15—H15A	0.9600
C4—C5	1.330 (4)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.485 (4)	C16—C18	1.511 (5)
C5—C16	1.501 (4)	C16—C17	1.515 (5)
C6—O1	1.224 (4)	C16—H16	0.9800
C6—C7	1.512 (5)	C17—H17A	0.9600
C7—C8	1.522 (4)	C17—H17B	0.9600
C7—H7	0.9800	C17—H17C	0.9600
C8—C9	1.478 (4)	C18—H18A	0.9600
C8—H8A	0.9700	C18—H18B	0.9600
C8—H8B	0.9700	C18—H18C	0.9600
C9—C10	1.317 (4)	C19—H19A	0.9600
C9—H9	0.9300	C19—H19B	0.9600
C10—C11	1.496 (5)	C19—H19C	0.9600
C11—C12	1.505 (6)	O2—H2o	0.8200
C11—H11A	0.9700

C10—C1—C14	110.3 (3)	H11A—C11—H11B	107.9
C10—C1—C2	113.7 (2)	C13—C12—C11	109.6 (4)
C14—C1—C2	115.8 (3)	C13—C12—H12A	109.7
C10—C1—H1	105.3	C11—C12—H12A	109.7
C14—C1—H1	105.3	C13—C12—H12B	109.7
C2—C1—H1	105.3	C11—C12—H12B	109.7
C7—C2—C15	106.6 (3)	H12A—C12—H12B	108.2
C7—C2—C3	108.0 (2)	C12—C13—C14	114.1 (3)
C15—C2—C3	108.3 (2)	C12—C13—H13A	108.7
C7—C2—C1	111.3 (2)	C14—C13—H13A	108.7
C15—C2—C1	109.4 (2)	C12—C13—H13B	108.7
C3—C2—C1	113.0 (2)	C14—C13—H13B	108.7
O2—C3—C4	109.3 (2)	H13A—C13—H13B	107.6
O2—C3—C2	110.2 (2)	C19—C14—C13	106.9 (3)
C4—C3—C2	112.8 (2)	C19—C14—C1	115.2 (4)
O2—C3—H3	108.1	C13—C14—C1	111.5 (3)
C4—C3—H3	108.1	C19—C14—H14	107.6
C2—C3—H3	108.1	C13—C14—H14	107.6
C5—C4—C3	126.5 (3)	C1—C14—H14	107.6
C5—C4—H4	116.8	C2—C15—H15A	109.5
C3—C4—H4	116.8	C2—C15—H15B	109.5
C4—C5—C6	117.5 (3)	H15A—C15—H15B	109.5
C4—C5—C16	125.5 (3)	C2—C15—H15C	109.5
C6—C5—C16	117.0 (3)	H15A—C15—H15C	109.5
O1—C6—C5	120.6 (3)	H15B—C15—H15C	109.5
O1—C6—C7	120.0 (3)	C5—C16—C18	113.0 (3)
C5—C6—C7	119.2 (3)	C5—C16—C17	109.8 (3)
C6—C7—C8	107.5 (3)	C18—C16—C17	110.9 (3)
C6—C7—C2	113.6 (2)	C5—C16—H16	107.6
C8—C7—C2	114.4 (3)	C18—C16—H16	107.6
C6—C7—H7	107.0	C17—C16—H16	107.6
C8—C7—H7	107.0	C16—C17—H17A	109.5
C2—C7—H7	107.0	C16—C17—H17B	109.5
C9—C8—C7	109.8 (3)	H17A—C17—H17B	109.5
C9—C8—H8A	109.7	C16—C17—H17C	109.5
C7—C8—H8A	109.7	H17A—C17—H17C	109.5
C9—C8—H8B	109.7	H17B—C17—H17C	109.5
C7—C8—H8B	109.7	C16—C18—H18A	109.5
H8A—C8—H8B	108.2	C16—C18—H18B	109.5
C10—C9—C8	124.9 (3)	H18A—C18—H18B	109.5
C10—C9—H9	117.6	C16—C18—H18C	109.5
C8—C9—H9	117.6	H18A—C18—H18C	109.5
C9—C10—C11	120.5 (3)	H18B—C18—H18C	109.5
C9—C10—C1	124.1 (3)	C14—C19—H19A	109.5
C11—C10—C1	115.2 (3)	C14—C19—H19B	109.5
C10—C11—C12	112.2 (4)	H19A—C19—H19B	109.5
C10—C11—H11A	109.2	C14—C19—H19C	109.5
C12—C11—H11A	109.2	H19A—C19—H19C	109.5
C10—C11—H11B	109.2	H19B—C19—H19C	109.5
C12—C11—H11B	109.2	C3—O2—H2o	109.5

C10—C1—C2—C7	−26.9 (3)	C15—C2—C7—C8	171.6 (3)
C14—C1—C2—C7	−156.1 (3)	C3—C2—C7—C8	−72.2 (3)
C10—C1—C2—C15	−144.5 (3)	C1—C2—C7—C8	52.4 (3)
C14—C1—C2—C15	86.3 (4)	C6—C7—C8—C9	−176.9 (3)
C10—C1—C2—C3	94.8 (3)	C2—C7—C8—C9	−49.8 (4)
C14—C1—C2—C3	−34.5 (4)	C7—C8—C9—C10	23.6 (5)
C7—C2—C3—O2	74.3 (3)	C8—C9—C10—C11	−176.3 (3)
C15—C2—C3—O2	−170.6 (3)	C8—C9—C10—C1	0.0 (6)
C1—C2—C3—O2	−49.2 (3)	C14—C1—C10—C9	133.7 (4)
C7—C2—C3—C4	−48.2 (3)	C2—C1—C10—C9	1.7 (5)
C15—C2—C3—C4	67.0 (3)	C14—C1—C10—C11	−49.8 (4)
C1—C2—C3—C4	−171.7 (3)	C2—C1—C10—C11	178.2 (3)
O2—C3—C4—C5	−99.1 (4)	C9—C10—C11—C12	−128.9 (4)
C2—C3—C4—C5	23.9 (4)	C1—C10—C11—C12	54.5 (5)
C3—C4—C5—C6	0.8 (5)	C10—C11—C12—C13	−55.1 (5)
C3—C4—C5—C16	−179.5 (3)	C11—C12—C13—C14	55.9 (5)
C4—C5—C6—O1	176.7 (3)	C12—C13—C14—C19	−179.9 (4)
C16—C5—C6—O1	−3.1 (5)	C12—C13—C14—C1	−53.1 (5)
C4—C5—C6—C7	2.3 (4)	C10—C1—C14—C19	169.7 (3)
C16—C5—C6—C7	−177.4 (3)	C2—C1—C14—C19	−59.4 (4)
O1—C6—C7—C8	−77.0 (4)	C10—C1—C14—C13	47.6 (4)
C5—C6—C7—C8	97.4 (3)	C2—C1—C14—C13	178.5 (3)
O1—C6—C7—C2	155.4 (3)	C4—C5—C16—C18	−18.6 (5)
C5—C6—C7—C2	−30.2 (4)	C6—C5—C16—C18	161.2 (3)
C15—C2—C7—C6	−64.5 (3)	C4—C5—C16—C17	105.8 (4)
C3—C2—C7—C6	51.7 (3)	C6—C5—C16—C17	−74.5 (4)
C1—C2—C7—C6	176.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O1ⁱ	0.82	2.02	2.804 (3)	160

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₈O₂
M_r	288.41
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	290
a, b, c (Å)	6.5507 (9), 11.733 (1), 22.338 (3)
V (Å³)	1716.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.15 × 0.12 × 0.09

Data collection
Diffractometer	Enraf–Nonius CAD-4 Mach 3
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2272, 1945, 1077
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.122, 1.02
No. of reflections	1945
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.11

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
O2—H2o···O1ⁱ	0.82	2.02	2.804 (3)	160

Symmetry code: (i) x−1, y, 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\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(4R*,4aS*,4bS*,5R*,10aR*)-4-Hy­dr­oxy-4a,5-di­methyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-deca­hydro­phenan­thren-1-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(4R,4aS,4bS,5R,10aR*)-4-Hydroxy-4a,5-dimethyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-decahydrophenanthren-1-one