(4R,4aS,4bS,7R,10aR)-4-Hy­droxy-4a,7-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/S1600536811044540

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3136

doi:10.1107/S1600536811044540

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(4R,4aS,4bS,7R,10aR)-4-Hydroxy-4a,7-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, Universidade Federal de São Carlos, Departamento de Química, CP 676, 13565-905, São Carlos, SP, Brazil, ^cDepartment of Chemistry, 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 24 October 2011; accepted 25 October 2011; online 29 October 2011)

In the title compound, C₁₉H₂₈O₂, the A ring adopts a chair conformation, and each of the B and C rings adopts a distorted half-chair conformation with the methine C atom in the CH₂C(H)C(=O) residue, common to both rings, lying 0.6397 (19) and 0.6328 (18) Å out of the approximate plane defined by the remaining five C atoms (r.m.s. deviations = 0.0791 and 0.0901 Å for rings B and C, respectively). Helical supramolecular chains along the a axis mediated by hydroxy–carbonyl O—H⋯O hydrogen bonds feature in 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 = 7.3029 (9) Å
b = 13.211 (2) Å
c = 17.224 (3) Å
V = 1661.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 290 K
0.12 × 0.08 × 0.07 mm

Data collection

Enraf–Nonius CAD-4 MACH 3 diffractometer
3684 measured reflections
3243 independent reflections
2253 reflections with I > 2σ(I)
R_int = 0.031
3 standard reflections every 30 min intensity decay: 1.1%

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.113
S = 1.04
3243 reflections
195 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 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	2.01	2.805 (2)	162
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: 10.1107/S1600536811044540/hg5120sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811044540/hg5120Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811044540/hg5120Isup3.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.

The A ring has a chair conformation. Each of the B and C rings presents a distorted half-chair conformation with atom C7, common to both rings, lying 0.6397 (19) and 0.6328 (18) Å, for B and C, respectively, out of the approximate plane defined by the remaining five C atoms (r.m.s. deviations = 0.0791 and 0.0901, respectively). The ring puckering parameters are: q₂ = 0.003 (2), 0.360 (2), 0.363 (2) Å; q₃ = 0.570 (2), -0.315 (2), -0.332 (2) Å; QT = 0.570 (2), 0.478 (2), 0.492 (2) Å; and θ = 1.7 (2), 131.1 (2), 132.5 (2)°, 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 supramolecular helical chains along the a axis, Fig. 2 and Table 1.

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; M.pt: 466.2–468.1 K. ¹H-NMR (CDCl₃, 400 MHz): δ (p.p.m.): 6.44 (d, 1H, J = 3.8 Hz); 5.26 (s, 1H); 4.58 (s, 1H); 2.81–2.87 (m, 1H); 2.86–2.92 (m, 1H); 2.24 (d, 1H, J = 6.4 Hz); 2.10–2.26 (m, 2H); 1.90–2.10 (m, 2H); 1.82–2.10 (m, 1H); 1.37–1.54 (m, 4H); 1.27 (s, 3H); 1.04 (d, 3H, J = 6.8 Hz); 1.01 (d, 3H, J = 6.8 Hz); 0.73 (d, 3H, J = 6.8 Hz); δ(OH) not obs. ¹³C (CDCl₃, 100 MHz) δ (p.p.m.): 197.9; 144.4; 142.7; 135.5; 117.2; 76.1; 49.6; 49.5; 45.9; 44.6; 35.7; 35.6; 33.6; 23.6; 22.3; 21.7; 21.5; 20.2; 20.0. Analysis found: C 78.99, H 9.77%. C₁₉H₂₈O₂ requires: C 79.12, H 9.79%.

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 helical supramolecular chain along the a axis in (I). The hydroxy-O—H···O(carbonyl) hydrogen bonds are represented by orange dashed lines.

(4R,4aS,4 bS,7R,10aR)- 4-Hydroxy-4a,7-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 = 1.153 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 7.3029 (9) Å	θ = 9.2–14.3°
b = 13.211 (2) Å	µ = 0.07 mm⁻¹
c = 17.224 (3) Å	T = 290 K
V = 1661.8 (4) Å³	Irregular, colourless
Z = 4	0.12 × 0.08 × 0.07 mm

Data collection top

Enraf–Nonius CAD-4 MACH 3 diffractometer	R_int = 0.031
Radiation source: fine-focus sealed tube	θ_max = 26.0°, θ_min = 1.9°
Graphite monochromator	h = 0→8
ω/–2θ scans	k = 0→16
3684 measured reflections	l = −21→21
3243 independent reflections	3 standard reflections every 30 min
2253 reflections with I > 2σ(I)	intensity decay: 1.1%

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) = 0.113	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0653P)² + 0.0421P] where P = (F_o² + 2F_c²)/3
3243 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₉H₂₈O₂	V = 1661.8 (4) Å³
M_r = 288.41	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3029 (9) Å	µ = 0.07 mm⁻¹
b = 13.211 (2) Å	T = 290 K
c = 17.224 (3) Å	0.12 × 0.08 × 0.07 mm

Data collection top

Enraf–Nonius CAD-4 MACH 3 diffractometer	R_int = 0.031
3684 measured reflections	3 standard reflections every 30 min
3243 independent reflections	intensity decay: 1.1%
2253 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.04	Δρ_max = 0.15 e Å⁻³
3243 reflections	Δρ_min = −0.13 e Å⁻³
195 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	0.6835 (3)	0.92045 (14)	0.83208 (11)	0.0386 (4)
H1	0.5721	0.9042	0.8613	0.046*
C2	0.6251 (2)	0.99993 (14)	0.77072 (11)	0.0378 (4)
C3	0.5391 (2)	0.95441 (16)	0.69613 (12)	0.0457 (5)
H3	0.4762	1.0096	0.6691	0.055*
C4	0.6752 (3)	0.91091 (16)	0.64072 (11)	0.0448 (5)
H4	0.6311	0.8659	0.6036	0.054*
C5	0.8545 (2)	0.93064 (15)	0.63955 (10)	0.0387 (4)
C6	0.9268 (2)	0.99737 (15)	0.70073 (11)	0.0382 (4)
C7	0.7918 (3)	1.06323 (13)	0.74402 (11)	0.0417 (5)
H7	0.7468	1.1144	0.7075	0.050*
C8	0.8794 (3)	1.11916 (16)	0.81222 (12)	0.0498 (5)
H8A	0.9985	1.1447	0.7967	0.060*
H8B	0.8036	1.1766	0.8263	0.060*
C9	0.9011 (3)	1.05182 (15)	0.88050 (12)	0.0471 (5)
H9	0.9814	1.0725	0.9193	0.056*
C10	0.8151 (3)	0.96451 (16)	0.89061 (11)	0.0415 (4)
C11	0.8553 (3)	0.89695 (17)	0.95906 (12)	0.0571 (6)
H11A	0.7435	0.8853	0.9881	0.068*
H11B	0.9424	0.9300	0.9932	0.068*
C12	0.9340 (4)	0.79528 (18)	0.93174 (14)	0.0613 (7)
H12	0.9403	0.7499	0.9767	0.074*
C13	0.8019 (4)	0.74886 (17)	0.87258 (13)	0.0626 (7)
H13A	0.8539	0.6862	0.8532	0.075*
H13B	0.6878	0.7324	0.8985	0.075*
C14	0.7615 (3)	0.81779 (14)	0.80467 (12)	0.0462 (5)
H14A	0.6739	0.7852	0.7705	0.055*
H14B	0.8731	0.8292	0.7755	0.055*
C15	0.4816 (3)	1.06970 (16)	0.80839 (13)	0.0520 (5)
H15A	0.4561	1.1254	0.7743	0.078*
H15B	0.5282	1.0950	0.8568	0.078*
H15C	0.3711	1.0322	0.8176	0.078*
C16	0.9912 (3)	0.88187 (16)	0.58484 (11)	0.0439 (5)
H16	1.0830	0.8479	0.6172	0.053*
C17	1.0923 (3)	0.95967 (18)	0.53606 (13)	0.0618 (6)
H17A	1.1538	1.0067	0.5696	0.093*
H17B	1.0064	0.9954	0.5040	0.093*
H17C	1.1806	0.9260	0.5038	0.093*
C18	0.9070 (3)	0.80139 (17)	0.53282 (14)	0.0597 (6)
H18A	0.8167	0.8319	0.4998	0.090*
H18B	0.8501	0.7503	0.5643	0.090*
H18C	1.0009	0.7711	0.5015	0.090*
C19	1.1271 (4)	0.8076 (2)	0.89947 (16)	0.0762 (8)
H19A	1.1246	0.8534	0.8562	0.114*
H19B	1.1724	0.7430	0.8827	0.114*
H19C	1.2058	0.8343	0.9392	0.114*
O1	1.09041 (18)	1.00004 (12)	0.71585 (9)	0.0548 (4)
O2	0.4059 (2)	0.87899 (12)	0.71243 (11)	0.0637 (5)
H2o	0.3032	0.9036	0.7089	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0338 (9)	0.0390 (10)	0.0431 (10)	0.0005 (8)	0.0042 (8)	0.0009 (8)
C2	0.0291 (9)	0.0410 (10)	0.0433 (10)	0.0040 (8)	−0.0015 (8)	−0.0020 (9)
C3	0.0289 (9)	0.0551 (12)	0.0531 (11)	0.0041 (8)	−0.0081 (8)	−0.0028 (10)
C4	0.0362 (10)	0.0579 (13)	0.0403 (10)	0.0065 (9)	−0.0090 (8)	−0.0087 (10)
C5	0.0311 (10)	0.0456 (10)	0.0395 (10)	0.0037 (8)	−0.0032 (7)	0.0031 (9)
C6	0.0313 (9)	0.0415 (10)	0.0419 (10)	−0.0020 (8)	−0.0019 (8)	0.0072 (9)
C7	0.0419 (11)	0.0357 (10)	0.0476 (11)	0.0007 (9)	−0.0046 (8)	0.0046 (9)
C8	0.0495 (12)	0.0389 (10)	0.0611 (13)	−0.0058 (10)	−0.0002 (10)	−0.0079 (10)
C9	0.0450 (11)	0.0497 (12)	0.0465 (11)	0.0010 (10)	−0.0085 (9)	−0.0142 (9)
C10	0.0393 (10)	0.0458 (11)	0.0393 (10)	0.0087 (9)	0.0003 (8)	−0.0045 (9)
C11	0.0652 (15)	0.0656 (14)	0.0404 (11)	0.0150 (12)	0.0001 (10)	0.0004 (10)
C12	0.0764 (16)	0.0607 (14)	0.0467 (12)	0.0222 (13)	0.0046 (11)	0.0148 (11)
C13	0.0857 (18)	0.0395 (12)	0.0626 (14)	0.0097 (12)	0.0142 (13)	0.0084 (11)
C14	0.0527 (11)	0.0352 (10)	0.0507 (11)	−0.0007 (9)	−0.0008 (10)	−0.0012 (9)
C15	0.0426 (11)	0.0572 (12)	0.0563 (12)	0.0147 (10)	−0.0011 (10)	−0.0066 (11)
C16	0.0340 (10)	0.0536 (12)	0.0440 (11)	0.0109 (10)	−0.0015 (9)	−0.0001 (9)
C17	0.0585 (14)	0.0705 (15)	0.0565 (13)	0.0026 (13)	0.0138 (12)	0.0031 (12)
C18	0.0542 (13)	0.0635 (14)	0.0615 (14)	0.0150 (12)	−0.0001 (12)	−0.0155 (11)
C19	0.0692 (17)	0.0917 (19)	0.0677 (15)	0.0340 (16)	−0.0017 (13)	0.0006 (15)
O1	0.0310 (7)	0.0714 (10)	0.0622 (10)	−0.0043 (7)	−0.0035 (7)	−0.0086 (8)
O2	0.0282 (7)	0.0769 (11)	0.0861 (12)	−0.0086 (8)	−0.0018 (8)	−0.0182 (9)

Geometric parameters (Å, º) top

C1—C10	1.510 (3)	C11—H11B	0.9700
C1—C14	1.545 (3)	C12—C19	1.524 (4)
C1—C2	1.550 (3)	C12—C13	1.532 (4)
C1—H1	0.9800	C12—H12	0.9800
C2—C15	1.539 (3)	C13—C14	1.511 (3)
C2—C7	1.547 (3)	C13—H13A	0.9700
C2—C3	1.551 (3)	C13—H13B	0.9700
C3—O2	1.421 (3)	C14—H14A	0.9700
C3—C4	1.493 (3)	C14—H14B	0.9700
C3—H3	0.9800	C15—H15A	0.9600
C4—C5	1.335 (3)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.472 (3)	C16—C17	1.519 (3)
C5—C16	1.517 (3)	C16—C18	1.520 (3)
C6—O1	1.223 (2)	C16—H16	0.9800
C6—C7	1.512 (3)	C17—H17A	0.9600
C7—C8	1.528 (3)	C17—H17B	0.9600
C7—H7	0.9800	C17—H17C	0.9600
C8—C9	1.483 (3)	C18—H18A	0.9600
C8—H8A	0.9700	C18—H18B	0.9600
C8—H8B	0.9700	C18—H18C	0.9600
C9—C10	1.325 (3)	C19—H19A	0.9600
C9—H9	0.9300	C19—H19B	0.9600
C10—C11	1.507 (3)	C19—H19C	0.9600
C11—C12	1.535 (3)	O2—H2o	0.8200
C11—H11A	0.9700

C10—C1—C14	107.93 (16)	H11A—C11—H11B	108.1
C10—C1—C2	111.68 (15)	C19—C12—C13	112.5 (2)
C14—C1—C2	119.21 (15)	C19—C12—C11	111.4 (2)
C10—C1—H1	105.7	C13—C12—C11	108.6 (2)
C14—C1—H1	105.7	C19—C12—H12	108.1
C2—C1—H1	105.7	C13—C12—H12	108.1
C15—C2—C7	109.71 (16)	C11—C12—H12	108.1
C15—C2—C1	107.80 (15)	C14—C13—C12	113.36 (19)
C7—C2—C1	110.64 (15)	C14—C13—H13A	108.9
C15—C2—C3	107.81 (15)	C12—C13—H13A	108.9
C7—C2—C3	106.38 (15)	C14—C13—H13B	108.9
C1—C2—C3	114.42 (16)	C12—C13—H13B	108.9
O2—C3—C4	108.20 (17)	H13A—C13—H13B	107.7
O2—C3—C2	112.67 (17)	C13—C14—C1	111.38 (16)
C4—C3—C2	114.15 (15)	C13—C14—H14A	109.4
O2—C3—H3	107.1	C1—C14—H14A	109.4
C4—C3—H3	107.1	C13—C14—H14B	109.4
C2—C3—H3	107.1	C1—C14—H14B	109.4
C5—C4—C3	125.97 (18)	H14A—C14—H14B	108.0
C5—C4—H4	117.0	C2—C15—H15A	109.5
C3—C4—H4	117.0	C2—C15—H15B	109.5
C4—C5—C6	117.27 (17)	H15A—C15—H15B	109.5
C4—C5—C16	124.90 (18)	C2—C15—H15C	109.5
C6—C5—C16	117.57 (16)	H15A—C15—H15C	109.5
O1—C6—C5	121.36 (18)	H15B—C15—H15C	109.5
O1—C6—C7	121.03 (18)	C5—C16—C17	112.10 (17)
C5—C6—C7	117.61 (15)	C5—C16—C18	113.38 (17)
C6—C7—C8	112.58 (17)	C17—C16—C18	110.12 (18)
C6—C7—C2	110.42 (15)	C5—C16—H16	107.0
C8—C7—C2	111.26 (16)	C17—C16—H16	107.0
C6—C7—H7	107.4	C18—C16—H16	107.0
C8—C7—H7	107.4	C16—C17—H17A	109.5
C2—C7—H7	107.4	C16—C17—H17B	109.5
C9—C8—C7	111.36 (16)	H17A—C17—H17B	109.5
C9—C8—H8A	109.4	C16—C17—H17C	109.5
C7—C8—H8A	109.4	H17A—C17—H17C	109.5
C9—C8—H8B	109.4	H17B—C17—H17C	109.5
C7—C8—H8B	109.4	C16—C18—H18A	109.5
H8A—C8—H8B	108.0	C16—C18—H18B	109.5
C10—C9—C8	125.16 (18)	H18A—C18—H18B	109.5
C10—C9—H9	117.4	C16—C18—H18C	109.5
C8—C9—H9	117.4	H18A—C18—H18C	109.5
C9—C10—C11	121.7 (2)	H18B—C18—H18C	109.5
C9—C10—C1	123.35 (18)	C12—C19—H19A	109.5
C11—C10—C1	114.70 (18)	C12—C19—H19B	109.5
C10—C11—C12	110.57 (17)	H19A—C19—H19B	109.5
C10—C11—H11A	109.5	C12—C19—H19C	109.5
C12—C11—H11A	109.5	H19A—C19—H19C	109.5
C10—C11—H11B	109.5	H19B—C19—H19C	109.5
C12—C11—H11B	109.5	C3—O2—H2o	109.5

C10—C1—C2—C15	−77.5 (2)	C3—C2—C7—C6	−58.80 (19)
C14—C1—C2—C15	155.54 (17)	C15—C2—C7—C8	59.1 (2)
C10—C1—C2—C7	42.5 (2)	C1—C2—C7—C8	−59.7 (2)
C14—C1—C2—C7	−84.5 (2)	C3—C2—C7—C8	175.44 (16)
C10—C1—C2—C3	162.63 (15)	C6—C7—C8—C9	−79.0 (2)
C14—C1—C2—C3	35.6 (2)	C2—C7—C8—C9	45.5 (2)
C15—C2—C3—O2	−73.6 (2)	C7—C8—C9—C10	−17.0 (3)
C7—C2—C3—O2	168.73 (15)	C8—C9—C10—C11	175.48 (19)
C1—C2—C3—O2	46.3 (2)	C8—C9—C10—C1	1.1 (3)
C15—C2—C3—C4	162.42 (17)	C14—C1—C10—C9	118.6 (2)
C7—C2—C3—C4	44.8 (2)	C2—C1—C10—C9	−14.3 (3)
C1—C2—C3—C4	−77.7 (2)	C14—C1—C10—C11	−56.2 (2)
O2—C3—C4—C5	−144.8 (2)	C2—C1—C10—C11	170.94 (16)
C2—C3—C4—C5	−18.5 (3)	C9—C10—C11—C12	−116.8 (2)
C3—C4—C5—C6	3.3 (3)	C1—C10—C11—C12	58.0 (3)
C3—C4—C5—C16	177.17 (19)	C10—C11—C12—C19	70.1 (3)
C4—C5—C6—O1	162.0 (2)	C10—C11—C12—C13	−54.3 (3)
C16—C5—C6—O1	−12.4 (3)	C19—C12—C13—C14	−68.0 (3)
C4—C5—C6—C7	−18.4 (3)	C11—C12—C13—C14	55.8 (3)
C16—C5—C6—C7	167.19 (17)	C12—C13—C14—C1	−56.9 (3)
O1—C6—C7—C8	−7.3 (3)	C10—C1—C14—C13	54.0 (2)
C5—C6—C7—C8	173.06 (16)	C2—C1—C14—C13	−177.28 (19)
O1—C6—C7—C2	−132.3 (2)	C4—C5—C16—C17	121.9 (2)
C5—C6—C7—C2	48.0 (2)	C6—C5—C16—C17	−64.2 (2)
C15—C2—C7—C6	−175.15 (16)	C4—C5—C16—C18	−3.5 (3)
C1—C2—C7—C6	66.04 (19)	C6—C5—C16—C18	170.39 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O1ⁱ	0.82	2.01	2.805 (2)	162

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)	7.3029 (9), 13.211 (2), 17.224 (3)
V (Å³)	1661.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.12 × 0.08 × 0.07

Data collection
Diffractometer	Enraf–Nonius CAD-4 MACH 3 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3684, 3243, 2253
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.113, 1.04
No. of reflections	3243
No. of parameters	195
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.13

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	2.01	2.805 (2)	162

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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Volume 67| Part 11| November 2011| Page o3136

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

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