6-Hydr­oxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexa­hydro­phenanthren-9(1H)-one

Rajouani, N.; Ait Itto, My.Y.; Benharref, A.; Auhmani, A.; Daran, J.-C.

doi:10.1107/S1600536808007769

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o762

doi:10.1107/S1600536808007769

Open

access

6-Hydroxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexahydrophenanthren-9(1H)-one

Nezha Rajouani,^a My Youssef Ait Itto,^a Ahmed Benharref,^a Aziz Auhmani ^a and Jean-Claude Daran ^b ^*

^aLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, Université Cadi Ayyad, Faculté des Sciences Semlalia, BP 2390 Marrakech, Morocco, and ^bLaboratoire de Chimie de Coordination, UPR-CNRS 8241, 205 route de Narbonne, 31077 Toulouse cédex, France
^*Correspondence e-mail: daran@lcc-toulouse.fr

(Received 12 March 2008; accepted 21 March 2008; online 29 March 2008)

The title compound, C₂₀H₂₈O₂, 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 ¹H and ¹³C NMR. The cyclohexane ring adopts a flattened chair conformation, while the cyclohexene ring adopts an envelope conformation. The molecules 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_r = 300.42
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.154
S = 1.05
2003 reflections
205 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.38 e Å⁻³

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) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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 ).

Supporting information

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

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

checkCIF report

Comment top

Juniperus oxycedrus L. has been used in traditional folk medicine for the treatment of chronic eczema and other several skin diseases (Bouhlal et al., 1988). Diterpenes are among the identified chemical constituents of this plant. They are of great interest with respect to their biological activity including antitumor, antituberculous and antimalarial effects (Iwamato et al., 2003; Politi et al., 2003; Ulubelen et al., 1997).

The structure of the title compound is built up by three fused six-membered rings A, B and C (Fig. 1). B displays an envelope conformation with puckering parameters, Q=0.510 (4) Å, θ= 124.6 (4)° and ϕ= 227.1 (6)° (Cremer & Pople, 1975) whereas C has a flattened chair conformation with Q= 0.546 (4) Å, θ = 5.0 (4) and ϕ = 234 (5)°. A is an aromatic ring and it is perfectly planar. The molecules are linked through O—H···O hydrogen bonds involving the hydroxyl group as a donor and the ketone oxygen as an acceptor yielding a zig zag chain developing parallel to the c axis (Fig. 2, Table 1).

Related literature top

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 top

In order to isolate similar compounds, we have studied the chemical composition of the fruits of Juniperus oxycedrus L. Thus, 203 g of pulverized cones was extracted with hexane. The solvent was evaporated under reduced pressure to give 14.3 g of the crude hexanic extract which was purified on silica gel column chromatography using hexane–AcOEt (97:3) as eluent, to give crystals of Sugiol (I). All ¹H and ¹³C NMR spectroscopic data of the isolated product were in full accord with the litterature (Bai-Ping & Isao, 1991).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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).

Figures top

	Fig. 1. Molecular view of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view of the compound, showing the formation of the zig zag chain parallel to the c axis and built from O—H···O hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted for clarity. [symmetry codes: (i) -x + 1/2,-y + 1, z + 1/2].

6-Hydroxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexahydrophenanthren- 9(1H)-one top

Crystal data top

C₂₀H₂₈O₂	F(000) = 656
M_r = 300.42	D_x = 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 = 2.7–32.1°
b = 12.6617 (6) Å	µ = 0.07 mm⁻¹
c = 14.0920 (7) Å	T = 180 K
V = 1713.99 (14) Å³	Flattened box, colorless
Z = 4	0.31 × 0.16 × 0.07 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	1212 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.068
Graphite monochromator	θ_max = 26.4°, θ_min = 2.7°
Detector resolution: 8.2632 pixels mm^-1	h = −12→12
ω and ϕ scans	k = −15→15
13398 measured reflections	l = −14→17
2003 independent reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0842P)²] where P = (F_o² + 2F_c²)/3
2003 reflections	(Δ/σ)_max < 0.001
205 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₀H₂₈O₂	V = 1713.99 (14) Å³
M_r = 300.42	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.6060 (4) Å	µ = 0.07 mm⁻¹
b = 12.6617 (6) Å	T = 180 K
c = 14.0920 (7) Å	0.31 × 0.16 × 0.07 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	1212 reflections with I > 2σ(I)
13398 measured reflections	R_int = 0.068
2003 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.05	Δρ_max = 0.36 e Å⁻³
2003 reflections	Δρ_min = −0.38 e Å⁻³
205 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₈O₂
M_r	300.42
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	180
a, b, c (Å)	9.6060 (4), 12.6617 (6), 14.0920 (7)
V (Å³)	1713.99 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.31 × 0.16 × 0.07

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13398, 2003, 1212
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.154, 1.05
No. of reflections	2003
No. of parameters	205
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.38

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6···O9ⁱ	0.82	1.84	2.642 (4)	164.8

Symmetry code: (i) −x+1/2, −y+1, z+1/2.

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
Bai-Ping, Y. & Isao, K. (1991). Phytochemistry, 30, 1951–1955. Google Scholar
Bouhlal, K., Meynadier, J. M., Peyron, J. L., Peyron, L., Marion, J. P., Bonetti, G. & Meynadier, J. (1988). Parfums Cosmét. Arômes, 83, 73–82. CAS Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Iwamato, M., Minami, T., Tokuda, H., Ohtsu, H. & Tanaka, R. (2003). Planta Med. 69, 69–72. Web of Science PubMed Google Scholar
Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Politi, M., Braca, A., Tommasi, N. D., Morelli, I., Manunuta, A., Battinell, L. & Mazzanti, G. (2003). Planta Med. 69, 468–470. Web of Science PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ulubelen, A., Topcu, G. & Johansson, C. B. (1997). J. Nat. Prod. 60, 1275–1280. Web of Science CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o762

doi:10.1107/S1600536808007769

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

6-Hydr­­oxy-7-iso­propyl-1,1,4a-tri­methyl-2,3,4,4a,10,10a-hexa­hydro­phenanthren-9(1H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

6-Hydroxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,4a,10,10a-hexahydrophenanthren-9(1H)-one