6-Hydr-oxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexa-hydro-phenanthren-9(1H)-one.

The title compound, C(20)H(28)O(2), commonly named Sugiol, is a natural oxygenated diterpene that we have isolated for the first time from a hexane extract of the fruits of Juniperus Oxycedrus L. Its X-ray crystal structure determination confirms an abietane skeleton which was predicted by spectroscopic analysis, mainly by (1)H and (13)C NMR. The cyclo-hexane ring adopts a flattened chair conformation, while the cyclo-hexene ring adopts an envelope conformation. The mol-ecules are linked through O-H⋯O hydrogen bonds to form a zigzag chain extending parallel to the c axis.

Related literature

For related literature, see: Bai-Ping & Isao (1991 ▶); Bouhlal et al. (1988 ▶); Cremer & Pople (1975 ▶); Iwamato et al. (2003 ▶); Politi et al. (2003 ▶); Ulubelen et al. (1997 ▶).

Experimental

Crystal data

C20H28O2

M = 300.42

Orthorhombic,

a = 9.6060 (4) Å

b = 12.6617 (6) Å

c = 14.0920 (7) Å

V = 1713.99 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 180 (2) K

0.31 × 0.16 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: none

13398 measured reflections

2003 independent reflections

1212 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.154

S = 1.05

2003 reflections

205 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007769/pk2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007769/pk2088Isup2.hkl

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

C20H28O2	F000 = 656
Mr = 300.42	Dx = 1.164 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3571 reflections
a = 9.6060 (4) Å	θ = 2.7–32.1º
b = 12.6617 (6) Å	µ = 0.07 mm−1
c = 14.0920 (7) Å	T = 180 (2) K
V = 1713.99 (14) Å3	Flattened box, colorless
Z = 4	0.31 × 0.16 × 0.07 mm

Oxford Diffraction Xcalibur diffractometer	2003 independent reflections
Radiation source: fine-focus sealed tube	1212 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.068
Detector resolution: 8.2632 pixels mm-1	θmax = 26.4º
T = 180(2) K	θmin = 2.7º
ω and φ scans	h = −12→12
Absorption correction: none	k = −15→15
13398 measured reflections	l = −14→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.0842P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2003 reflections	Δρmax = 0.36 e Å−3
205 parameters	Δρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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	0.0789 (4)	0.8588 (3)	0.0839 (3)	0.0291 (10)
C2	0.1754 (4)	0.9176 (3)	0.1515 (3)	0.0339 (11)
H2A	0.2674	0.9211	0.1234	0.041*
H2B	0.1418	0.9894	0.1588	0.041*
C3	0.1869 (5)	0.8673 (3)	0.2486 (3)	0.0366 (11)
H3A	0.0966	0.8681	0.2794	0.044*
H3B	0.2511	0.9077	0.2874	0.044*
C4	0.2389 (4)	0.7525 (3)	0.2400 (3)	0.0296 (10)
H4A	0.2430	0.7215	0.3029	0.036*
H4B	0.3327	0.7531	0.2145	0.036*
C4A	0.1464 (4)	0.6828 (3)	0.1762 (3)	0.0217 (9)
C4B	0.2182 (4)	0.5776 (3)	0.1555 (3)	0.0202 (9)
C5	0.3090 (4)	0.5314 (3)	0.2203 (3)	0.0252 (9)
H5	0.3286	0.5661	0.2768	0.030*
C6	0.3699 (4)	0.4356 (3)	0.2023 (3)	0.0255 (9)
C7	0.3444 (4)	0.3792 (3)	0.1186 (3)	0.0296 (10)
C8	0.2533 (4)	0.4252 (3)	0.0564 (3)	0.0244 (10)
H8	0.2335	0.3898	0.0002	0.029*
C8A	0.1892 (4)	0.5211 (3)	0.0724 (3)	0.0219 (9)
C9	0.0961 (4)	0.5626 (3)	0.0010 (3)	0.0220 (9)
C10	0.0395 (4)	0.6713 (3)	0.0137 (3)	0.0307 (10)
H10A	−0.0545	0.6663	0.0384	0.037*
H10B	0.0344	0.7054	−0.0479	0.037*
C10A	0.1257 (4)	0.7408 (3)	0.0804 (3)	0.0227 (9)
H10C	0.2186	0.7426	0.0518	0.027*
C11	0.0945 (5)	0.9073 (3)	−0.0143 (3)	0.0455 (13)
H11A	0.0847	0.9826	−0.0099	0.068*
H11B	0.0239	0.8795	−0.0556	0.068*
H11C	0.1847	0.8905	−0.0393	0.068*
C12	−0.0741 (4)	0.8754 (3)	0.1138 (3)	0.0397 (12)
H12A	−0.1013	0.9468	0.1006	0.060*
H12B	−0.0836	0.8618	0.1805	0.060*
H12C	−0.1328	0.8278	0.0790	0.060*
C13	0.0112 (4)	0.6551 (3)	0.2292 (3)	0.0333 (11)
H13A	−0.0494	0.6162	0.1879	0.050*
H13B	−0.0343	0.7190	0.2490	0.050*
H13C	0.0328	0.6130	0.2839	0.050*
C14	0.4133 (5)	0.2730 (3)	0.1025 (3)	0.0322 (11)
H14	0.5100	0.2792	0.1240	0.039*
C15	0.4171 (6)	0.2384 (4)	0.0019 (4)	0.0672 (18)
H15A	0.3239	0.2261	−0.0201	0.101*
H15B	0.4701	0.1743	−0.0032	0.101*
H15C	0.4598	0.2923	−0.0362	0.101*
C16	0.3443 (6)	0.1868 (4)	0.1627 (4)	0.0614 (16)
H16A	0.2516	0.1744	0.1399	0.092*
H16B	0.3406	0.2093	0.2277	0.092*
H16C	0.3976	0.1229	0.1582	0.092*
O6	0.4598 (3)	0.3917 (2)	0.2654 (2)	0.0353 (8)
H6	0.4641	0.4287	0.3131	0.053*
O9	0.0639 (3)	0.5113 (2)	−0.06942 (18)	0.0304 (7)

	U11	U22	U33	U12	U13	U23
C1	0.033 (2)	0.018 (2)	0.036 (2)	0.0086 (18)	−0.001 (2)	0.0033 (19)
C2	0.033 (2)	0.021 (2)	0.048 (3)	0.0042 (19)	0.000 (2)	−0.002 (2)
C3	0.032 (2)	0.029 (2)	0.048 (3)	0.001 (2)	−0.008 (2)	−0.014 (2)
C4	0.032 (2)	0.027 (2)	0.029 (2)	0.0046 (19)	−0.0046 (19)	−0.0085 (19)
C4A	0.022 (2)	0.021 (2)	0.022 (2)	−0.0028 (16)	−0.0010 (18)	0.0000 (17)
C4B	0.0183 (18)	0.0196 (19)	0.023 (2)	−0.0009 (16)	0.0041 (18)	0.0026 (17)
C5	0.028 (2)	0.025 (2)	0.023 (2)	−0.0008 (18)	0.000 (2)	−0.0038 (18)
C6	0.029 (2)	0.028 (2)	0.019 (2)	0.0069 (19)	0.0023 (18)	0.0033 (19)
C7	0.032 (3)	0.025 (2)	0.032 (2)	0.0043 (19)	0.007 (2)	0.002 (2)
C8	0.028 (2)	0.023 (2)	0.022 (2)	0.0025 (19)	−0.0002 (18)	0.0010 (18)
C8A	0.026 (2)	0.0196 (19)	0.020 (2)	−0.0039 (17)	−0.0026 (19)	0.0021 (18)
C9	0.024 (2)	0.021 (2)	0.020 (2)	−0.0005 (17)	0.0018 (18)	0.0018 (18)
C10	0.033 (2)	0.032 (2)	0.027 (2)	0.0024 (19)	−0.006 (2)	−0.0011 (19)
C10A	0.021 (2)	0.024 (2)	0.023 (2)	0.0048 (16)	−0.0008 (18)	−0.0035 (18)
C11	0.059 (3)	0.029 (3)	0.049 (3)	0.008 (2)	0.001 (3)	0.011 (2)
C12	0.035 (3)	0.035 (3)	0.048 (3)	0.013 (2)	−0.009 (2)	−0.010 (2)
C13	0.030 (2)	0.033 (2)	0.037 (3)	0.0033 (19)	0.003 (2)	0.003 (2)
C14	0.036 (3)	0.025 (2)	0.035 (2)	0.010 (2)	−0.002 (2)	0.0025 (18)
C15	0.093 (5)	0.065 (4)	0.044 (3)	0.045 (4)	0.001 (3)	−0.011 (3)
C16	0.067 (4)	0.036 (3)	0.080 (4)	0.006 (3)	0.017 (3)	0.006 (3)
O6	0.0436 (18)	0.0353 (17)	0.0271 (17)	0.0196 (15)	−0.0073 (15)	−0.0031 (14)
O9	0.0393 (17)	0.0288 (15)	0.0231 (15)	0.0002 (14)	−0.0061 (14)	−0.0076 (13)

C1—C11	1.521 (6)	C8A—C9	1.445 (5)
C1—C2	1.524 (6)	C9—O9	1.226 (4)
C1—C12	1.543 (6)	C9—C10	1.491 (5)
C1—C10A	1.561 (5)	C10—C10A	1.530 (5)
C2—C3	1.514 (6)	C10—H10A	0.9700
C2—H2A	0.9700	C10—H10B	0.9700
C2—H2B	0.9700	C10A—H10C	0.9800
C3—C4	1.542 (5)	C11—H11A	0.9600
C3—H3A	0.9700	C11—H11B	0.9600
C3—H3B	0.9700	C11—H11C	0.9600
C4—C4A	1.542 (5)	C12—H12A	0.9600
C4—H4A	0.9700	C12—H12B	0.9600
C4—H4B	0.9700	C12—H12C	0.9600
C4A—C4B	1.528 (5)	C13—H13A	0.9600
C4A—C13	1.539 (5)	C13—H13B	0.9600
C4A—C10A	1.550 (5)	C13—H13C	0.9600
C4B—C5	1.391 (5)	C14—C15	1.485 (6)
C4B—C8A	1.401 (5)	C14—C16	1.532 (6)
C5—C6	1.370 (5)	C14—H14	0.9800
C5—H5	0.9300	C15—H15A	0.9600
C6—O6	1.359 (4)	C15—H15B	0.9600
C6—C7	1.401 (5)	C15—H15C	0.9600
C7—C8	1.369 (5)	C16—H16A	0.9600
C7—C14	1.517 (5)	C16—H16B	0.9600
C8—C8A	1.380 (5)	C16—H16C	0.9600
C8—H8	0.9300	O6—H6	0.8200
C11—C1—C2	108.1 (4)	C8A—C9—C10	118.6 (3)
C11—C1—C12	106.7 (4)	C9—C10—C10A	114.0 (3)
C2—C1—C12	110.0 (3)	C9—C10—H10A	108.7
C11—C1—C10A	109.3 (3)	C10A—C10—H10A	108.7
C2—C1—C10A	108.2 (3)	C9—C10—H10B	108.7
C12—C1—C10A	114.4 (3)	C10A—C10—H10B	108.7
C3—C2—C1	113.9 (3)	H10A—C10—H10B	107.6
C3—C2—H2A	108.8	C10—C10A—C4A	109.4 (3)
C1—C2—H2A	108.8	C10—C10A—C1	114.4 (3)
C3—C2—H2B	108.8	C4A—C10A—C1	117.6 (3)
C1—C2—H2B	108.8	C10—C10A—H10C	104.6
H2A—C2—H2B	107.7	C4A—C10A—H10C	104.6
C2—C3—C4	110.4 (3)	C1—C10A—H10C	104.6
C2—C3—H3A	109.6	C1—C11—H11A	109.5
C4—C3—H3A	109.6	C1—C11—H11B	109.5
C2—C3—H3B	109.6	H11A—C11—H11B	109.5
C4—C3—H3B	109.6	C1—C11—H11C	109.5
H3A—C3—H3B	108.1	H11A—C11—H11C	109.5
C3—C4—C4A	113.5 (3)	H11B—C11—H11C	109.5
C3—C4—H4A	108.9	C1—C12—H12A	109.5
C4A—C4—H4A	108.9	C1—C12—H12B	109.5
C3—C4—H4B	108.9	H12A—C12—H12B	109.5
C4A—C4—H4B	108.9	C1—C12—H12C	109.5
H4A—C4—H4B	107.7	H12A—C12—H12C	109.5
C4B—C4A—C13	106.0 (3)	H12B—C12—H12C	109.5
C4B—C4A—C4	110.5 (3)	C4A—C13—H13A	109.5
C13—C4A—C4	109.5 (3)	C4A—C13—H13B	109.5
C4B—C4A—C10A	107.8 (3)	H13A—C13—H13B	109.5
C13—C4A—C10A	115.0 (3)	C4A—C13—H13C	109.5
C4—C4A—C10A	108.1 (3)	H13A—C13—H13C	109.5
C5—C4B—C8A	117.3 (3)	H13B—C13—H13C	109.5
C5—C4B—C4A	121.6 (3)	C15—C14—C7	114.6 (4)
C8A—C4B—C4A	121.0 (3)	C15—C14—C16	109.2 (4)
C6—C5—C4B	121.3 (4)	C7—C14—C16	111.0 (4)
C6—C5—H5	119.4	C15—C14—H14	107.2
C4B—C5—H5	119.4	C7—C14—H14	107.2
O6—C6—C5	120.9 (4)	C16—C14—H14	107.2
O6—C6—C7	117.0 (3)	C14—C15—H15A	109.5
C5—C6—C7	122.2 (4)	C14—C15—H15B	109.5
C8—C7—C6	115.8 (3)	H15A—C15—H15B	109.5
C8—C7—C14	124.1 (4)	C14—C15—H15C	109.5
C6—C7—C14	120.1 (4)	H15A—C15—H15C	109.5
C7—C8—C8A	123.7 (4)	H15B—C15—H15C	109.5
C7—C8—H8	118.2	C14—C16—H16A	109.5
C8A—C8—H8	118.2	C14—C16—H16B	109.5
C8—C8A—C4B	119.8 (4)	H16A—C16—H16B	109.5
C8—C8A—C9	118.9 (3)	C14—C16—H16C	109.5
C4B—C8A—C9	121.3 (3)	H16A—C16—H16C	109.5
O9—C9—C8A	121.7 (3)	H16B—C16—H16C	109.5
O9—C9—C10	119.6 (4)	C6—O6—H6	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O9i	0.82	1.84	2.642 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6⋯O9i	0.82	1.84	2.642 (4)	165

Symmetry code: (i) .