7-Hy-droxy-8-isopropyl-1,1,4a-trimethyl-4a,9,10,10a-tetra-hydro-phenanthren-2(1H)-one.

The title compound, C(20)H(26)O(2), was isolated from a chloro-form extract of Tetra-clinis articulata wood. The mol-ecule contains three fused rings which exhibit different conformations. The non-aromatic oxo-substituted ring has a screw-boat conformation, while the central ring has a half-chair conformation. In the crystal, mol-ecules are linked to each other by inter-molecular O-H⋯O hydrogen bonds involving the carbonyl and hy-droxy groups.

Related literature

For background to the biological activity of diterpenoids, see: Atta-ur-Rahman & Choudhary (1999 ▶); Azucena & Mobashery (2001 ▶); Panter et al. (2002 ▶); Ulusu et al. (2002 ▶). For their use in traditional medicine, see: Bellakhdar (1997 ▶) and for their medicinal properties, see: Barrero et al. (2003 ▶); Comte et al. (1995 ▶); Evidente et al. (1997 ▶). For the synthesis see: Zeroual et al. (2007 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C20H26O2

M = 298.41

Monoclinic,

a = 11.6731 (8) Å

b = 6.4314 (4) Å

c = 12.1488 (10) Å

β = 111.592 (9)°

V = 848.06 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 180 K

0.48 × 0.36 × 0.29 mm

Data collection

Agilent Xcalibur Eos Gemini ultra diffractometer

9252 measured reflections

1893 independent reflections

1591 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.128

S = 1.03

1893 reflections

207 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009561/fj2405sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009561/fj2405Isup2.hkl

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

C20H26O2	F(000) = 324
Mr = 298.41	Dx = 1.169 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3905 reflections
a = 11.6731 (8) Å	θ = 3.6–29.2°
b = 6.4314 (4) Å	µ = 0.07 mm−1
c = 12.1488 (10) Å	T = 180 K
β = 111.592 (9)°	Prism, colourless
V = 848.06 (11) Å3	0.48 × 0.36 × 0.29 mm
Z = 2

Agilent Xcalibur Eos Gemini ultra diffractometer	1591 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.066
graphite	θmax = 26.4°, θmin = 3.7°
Detector resolution: 16.1978 pixels mm-1	h = −14→14
ω scans	k = −8→8
9252 measured reflections	l = −15→15
1893 independent reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0659P)2 + 0.2266P] where P = (Fo2 + 2Fc2)/3
1893 reflections	(Δ/σ)max < 0.001
207 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.22 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 > 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.

	x	y	z	Uiso*/Ueq
C1	−0.3286 (2)	0.3531 (5)	0.7146 (2)	0.0290 (6)
C2	−0.4104 (2)	0.3898 (5)	0.5849 (3)	0.0314 (7)
C3	−0.3525 (3)	0.4063 (6)	0.4963 (3)	0.0364 (7)
H3	−0.4016	0.3822	0.4154	0.045 (10)*
C4	−0.2337 (3)	0.4540 (5)	0.5251 (3)	0.0324 (7)
H4	−0.2019	0.4667	0.4638	0.047 (10)*
C4A	−0.1473 (2)	0.4886 (5)	0.6526 (2)	0.0283 (6)
C4B	−0.0133 (2)	0.4386 (4)	0.6696 (2)	0.0274 (6)
C5	0.0337 (2)	0.5177 (5)	0.5876 (3)	0.0296 (6)
H5	−0.0179	0.6000	0.5237	0.036*
C6	0.1537 (2)	0.4788 (5)	0.5974 (3)	0.0303 (7)
H6	0.1846	0.5371	0.5420	0.036*
C7	0.2287 (2)	0.3544 (5)	0.6887 (2)	0.0299 (6)
C8	0.1866 (2)	0.2729 (5)	0.7742 (2)	0.0287 (6)
C8A	0.0651 (2)	0.3211 (5)	0.7647 (2)	0.0273 (6)
C9	0.0224 (2)	0.2470 (6)	0.8626 (3)	0.0351 (7)
H9A	0.0867	0.2814	0.9402	0.042*
H9B	0.0136	0.0938	0.8579	0.042*
C10	−0.0995 (2)	0.3422 (6)	0.8568 (2)	0.0336 (7)
H10A	−0.1329	0.2626	0.9079	0.040*
H10B	−0.0861	0.4875	0.8856	0.040*
C10A	−0.1905 (2)	0.3373 (5)	0.7292 (2)	0.0282 (6)
H10	−0.1817	0.1953	0.6997	0.034*
C11	0.2702 (3)	0.1345 (6)	0.8719 (3)	0.0383 (8)
H11	0.2229	0.0978	0.9231	0.046*
C12	0.3000 (3)	−0.0718 (6)	0.8246 (4)	0.0526 (9)
H12A	0.3534	−0.0452	0.7800	0.079*
H12B	0.2233	−0.1371	0.7725	0.079*
H21A	0.3421	−0.1649	0.8911	0.079*
C13	0.3870 (3)	0.2455 (7)	0.9521 (3)	0.0474 (9)
H13A	0.4396	0.2761	0.9071	0.071*
H13B	0.4317	0.1559	1.0195	0.071*
H13C	0.3646	0.3757	0.9810	0.071*
C15	−0.3538 (3)	0.5228 (6)	0.7922 (3)	0.0422 (8)
H15A	−0.4422	0.5272	0.7773	0.063*
H15B	−0.3274	0.6580	0.7727	0.063*
H15C	−0.3079	0.4913	0.8758	0.063*
C16	−0.3680 (3)	0.1419 (5)	0.7484 (3)	0.0371 (7)
H16A	−0.3634	0.0355	0.6925	0.056*
H16B	−0.4528	0.1515	0.7457	0.056*
H16C	−0.3130	0.1042	0.8286	0.056*
C18	−0.1553 (3)	0.7207 (5)	0.6809 (3)	0.0427 (8)
H18A	−0.1174	0.8047	0.6362	0.064*
H18B	−0.1117	0.7442	0.7658	0.064*
H18C	−0.2419	0.7606	0.6587	0.064*
O1	−0.52293 (18)	0.4045 (4)	0.5543 (2)	0.0440 (6)
O2	0.34674 (17)	0.3068 (4)	0.69940 (18)	0.0396 (6)
H2	0.3623	0.3635	0.6442	0.059*

	U11	U22	U33	U12	U13	U23
C1	0.0193 (12)	0.0352 (16)	0.0359 (15)	0.0034 (12)	0.0140 (11)	0.0023 (13)
C2	0.0210 (13)	0.0368 (17)	0.0389 (15)	0.0037 (12)	0.0138 (11)	0.0033 (13)
C3	0.0240 (14)	0.056 (2)	0.0299 (14)	0.0060 (14)	0.0106 (11)	0.0032 (14)
C4	0.0247 (14)	0.0416 (18)	0.0355 (15)	0.0089 (12)	0.0165 (12)	0.0062 (13)
C4A	0.0213 (13)	0.0343 (16)	0.0338 (14)	0.0029 (12)	0.0153 (11)	0.0026 (13)
C4B	0.0208 (13)	0.0313 (16)	0.0338 (14)	−0.0026 (11)	0.0145 (11)	−0.0017 (12)
C5	0.0245 (14)	0.0317 (15)	0.0345 (14)	0.0003 (12)	0.0129 (11)	0.0013 (12)
C6	0.0258 (14)	0.0365 (17)	0.0346 (14)	−0.0068 (13)	0.0182 (12)	−0.0015 (13)
C7	0.0166 (12)	0.0403 (17)	0.0354 (15)	−0.0036 (13)	0.0126 (11)	−0.0034 (14)
C8	0.0204 (13)	0.0335 (15)	0.0335 (14)	−0.0016 (12)	0.0115 (11)	0.0003 (12)
C8A	0.0180 (12)	0.0329 (15)	0.0334 (14)	−0.0017 (11)	0.0125 (11)	0.0000 (12)
C9	0.0195 (14)	0.0533 (19)	0.0340 (15)	−0.0013 (13)	0.0117 (11)	0.0041 (14)
C10	0.0235 (13)	0.0494 (19)	0.0310 (14)	−0.0024 (14)	0.0136 (11)	0.0025 (14)
C10A	0.0171 (12)	0.0396 (16)	0.0309 (14)	0.0030 (12)	0.0124 (10)	0.0005 (13)
C11	0.0193 (13)	0.055 (2)	0.0408 (16)	0.0001 (14)	0.0119 (12)	0.0067 (15)
C12	0.0414 (19)	0.049 (2)	0.061 (2)	0.0066 (16)	0.0101 (17)	0.0116 (18)
C13	0.0300 (17)	0.069 (3)	0.0414 (18)	−0.0075 (16)	0.0115 (14)	0.0022 (18)
C15	0.0279 (16)	0.053 (2)	0.054 (2)	−0.0006 (15)	0.0258 (15)	−0.0119 (17)
C16	0.0241 (14)	0.0423 (18)	0.0495 (18)	0.0017 (13)	0.0187 (13)	0.0097 (15)
C18	0.0426 (19)	0.0361 (19)	0.061 (2)	0.0025 (14)	0.0327 (17)	0.0003 (16)
O1	0.0197 (10)	0.0687 (17)	0.0459 (12)	0.0077 (10)	0.0146 (9)	0.0109 (12)
O2	0.0212 (10)	0.0626 (16)	0.0409 (12)	0.0021 (10)	0.0184 (9)	0.0044 (11)

C1—C2	1.531 (4)	C9—H9A	0.9900
C1—C16	1.538 (4)	C9—H9B	0.9900
C1—C15	1.539 (4)	C10—C10A	1.523 (4)
C1—C10A	1.559 (3)	C10—H10A	0.9900
C2—O1	1.230 (3)	C10—H10B	0.9900
C2—C3	1.471 (4)	C10A—H10	1.0000
C3—C4	1.336 (4)	C11—C13	1.530 (5)
C3—H3	0.9500	C11—C12	1.536 (5)
C4—C4A	1.522 (4)	C11—H11	1.0000
C4—H4	0.9500	C12—H12A	0.9800
C4A—C4B	1.535 (4)	C12—H12B	0.9800
C4A—C18	1.542 (4)	C12—H21A	0.9800
C4A—C10A	1.554 (4)	C13—H13A	0.9800
C4B—C5	1.397 (4)	C13—H13B	0.9800
C4B—C8A	1.401 (4)	C13—H13C	0.9800
C5—C6	1.385 (4)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C6—C7	1.386 (4)	C15—H15C	0.9800
C6—H6	0.9500	C16—H16A	0.9800
C7—O2	1.371 (3)	C16—H16B	0.9800
C7—C8	1.403 (4)	C16—H16C	0.9800
C8—C8A	1.414 (4)	C18—H18A	0.9800
C8—C11	1.517 (4)	C18—H18B	0.9800
C8A—C9	1.526 (4)	C18—H18C	0.9800
C9—C10	1.526 (4)	O2—H2	0.8400
C2—C1—C16	106.1 (2)	C9—C10—H10A	109.8
C2—C1—C15	109.5 (2)	C10A—C10—H10B	109.8
C16—C1—C15	108.7 (2)	C9—C10—H10B	109.8
C2—C1—C10A	110.7 (2)	H10A—C10—H10B	108.3
C16—C1—C10A	108.1 (2)	C10—C10A—C4A	109.7 (2)
C15—C1—C10A	113.5 (2)	C10—C10A—C1	114.8 (2)
O1—C2—C3	120.0 (3)	C4A—C10A—C1	116.2 (2)
O1—C2—C1	121.0 (2)	C10—C10A—H10	104.9
C3—C2—C1	119.0 (2)	C4A—C10A—H10	104.9
C4—C3—C2	122.5 (3)	C1—C10A—H10	104.9
C4—C3—H3	118.8	C8—C11—C13	113.0 (3)
C2—C3—H3	118.8	C8—C11—C12	112.5 (3)
C3—C4—C4A	122.4 (2)	C13—C11—C12	111.7 (3)
C3—C4—H4	118.8	C8—C11—H11	106.3
C4A—C4—H4	118.8	C13—C11—H11	106.3
C4—C4A—C4B	111.5 (2)	C12—C11—H11	106.3
C4—C4A—C18	107.3 (3)	C11—C12—H12A	109.5
C4B—C4A—C18	108.4 (3)	C11—C12—H12B	109.5
C4—C4A—C10A	106.2 (2)	H12A—C12—H12B	109.5
C4B—C4A—C10A	109.2 (2)	C11—C12—H21A	109.5
C18—C4A—C10A	114.4 (2)	H12A—C12—H21A	109.5
C5—C4B—C8A	118.4 (2)	H12B—C12—H21A	109.5
C5—C4B—C4A	118.4 (2)	C11—C13—H13A	109.5
C8A—C4B—C4A	123.2 (2)	C11—C13—H13B	109.5
C6—C5—C4B	121.5 (3)	H13A—C13—H13B	109.5
C6—C5—H5	119.2	C11—C13—H13C	109.5
C4B—C5—H5	119.2	H13A—C13—H13C	109.5
C5—C6—C7	119.6 (2)	H13B—C13—H13C	109.5
C5—C6—H6	120.2	C1—C15—H15A	109.5
C7—C6—H6	120.2	C1—C15—H15B	109.5
O2—C7—C6	121.4 (2)	H15A—C15—H15B	109.5
O2—C7—C8	117.4 (2)	C1—C15—H15C	109.5
C6—C7—C8	121.2 (2)	H15A—C15—H15C	109.5
C7—C8—C8A	118.1 (3)	H15B—C15—H15C	109.5
C7—C8—C11	119.9 (2)	C1—C16—H16A	109.5
C8A—C8—C11	122.0 (2)	C1—C16—H16B	109.5
C4B—C8A—C8	121.1 (2)	H16A—C16—H16B	109.5
C4B—C8A—C9	120.7 (2)	C1—C16—H16C	109.5
C8—C8A—C9	118.2 (2)	H16A—C16—H16C	109.5
C8A—C9—C10	113.9 (3)	H16B—C16—H16C	109.5
C8A—C9—H9A	108.8	C4A—C18—H18A	109.5
C10—C9—H9A	108.8	C4A—C18—H18B	109.5
C8A—C9—H9B	108.8	H18A—C18—H18B	109.5
C10—C9—H9B	108.8	C4A—C18—H18C	109.5
H9A—C9—H9B	107.7	H18A—C18—H18C	109.5
C10A—C10—C9	109.2 (2)	H18B—C18—H18C	109.5
C10A—C10—H10A	109.8	C7—O2—H2	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.84	2.03	2.791 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.84	2.03	2.791 (3)	150

Symmetry code: (i) .