(4R,4aS,4bS,7R,10aR)-4-Hy-droxy-4a,7-dimethyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-deca-hydro-phenanthren-1-one.

In the title compound, C(19)H(28)O(2), 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 CH(2)C(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 supra-molecular chains along the a axis mediated by hy-droxy-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 = 288.41

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.113

S = 1.04

3243 reflections

195 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.13 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044540/hg5120sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811044540/hg5120Isup3.cml

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

C19H28O2	F(000) = 632
Mr = 288.41	Dx = 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

Enraf–Nonius CAD-4 MACH 3 diffractometer	Rint = 0.031
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 1.9°
graphite	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 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(Fo2) + (0.0653P)2 + 0.0421P] where P = (Fo2 + 2Fc2)/3
3243 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .