6-Hydroxy-salvinolone.

The title compound {systematic name: 5,6,10-trihydr-oxy-7-iso-propyl-1,1,4a-trimethyl-2,3,4,4a-tetra-hydro-phenanthren-9(1H)-one}, C(20)H(26)O(4), is a diterpenoid which was isolated from the roots of Premna obtusifolia. The mol-ecule has three fused six-membered rings; the cyclo-hexane ring is in a twisted-boat conformation and the cyclo-hexene ring adopts a sofa form. Intra-molecular O-H⋯O hydrogen bonds generate two S(5) ring motifs. In the crystal, mol-ecules are linked into infinite one-dimensional chains along the [001] direction by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions.

Related literature

For hydrogen bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to diterpenes and their activities, see: Fraga et al. (2005 ▶); Hueso-Rodríguez et al. (1983 ▶); Topcu & Ulubelen (1996 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C20H26O4

M = 330.41

Orthorhombic,

a = 9.4946 (1) Å

b = 13.1716 (1) Å

c = 13.8124 (1) Å

V = 1727.37 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.35 × 0.30 × 0.27 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.970, T max = 0.977

36584 measured reflections

3890 independent reflections

3530 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.114

S = 1.09

3890 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034990/sj2639sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034990/sj2639Isup2.hkl

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

C20H26O4	F(000) = 712
Mr = 330.41	Dx = 1.271 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3890 reflections
a = 9.4946 (1) Å	θ = 2.1–34.0°
b = 13.1716 (1) Å	µ = 0.09 mm−1
c = 13.8124 (1) Å	T = 100 K
V = 1727.37 (3) Å3	Block, colourless
Z = 4	0.35 × 0.30 × 0.27 mm

Bruker APEXII CCD area-detector diffractometer	3890 independent reflections
Radiation source: sealed tube	3530 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 34.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.970, Tmax = 0.977	k = −20→19
36584 measured reflections	l = −21→21

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.065P)2 + 0.2832P] where P = (Fo2 + 2Fc2)/3
3890 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 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
O1	0.26452 (14)	0.14460 (7)	0.64485 (7)	0.0216 (2)
H1O1	0.269 (3)	0.2000 (18)	0.6119 (16)	0.041 (7)*
O2	0.25851 (15)	0.33755 (7)	0.66826 (6)	0.0238 (2)
O3	0.24282 (12)	0.46627 (7)	1.11140 (6)	0.01532 (17)
H1O3	0.2434	0.5285	1.1112	0.023*
O4	0.25735 (12)	0.27209 (7)	1.09834 (6)	0.01710 (18)
H1O4	0.255 (3)	0.3196 (17)	1.1358 (17)	0.036 (6)*
C1	0.14764 (15)	0.10997 (9)	0.98617 (9)	0.0161 (2)
H1A	0.1868	0.1047	1.0509	0.019*
H1B	0.0673	0.1553	0.9895	0.019*
C2	0.09602 (14)	0.00517 (10)	0.95499 (9)	0.0168 (2)
H2A	0.0690	−0.0333	1.0119	0.020*
H2B	0.0132	0.0129	0.9145	0.020*
C3	0.20820 (14)	−0.05358 (9)	0.89937 (9)	0.0152 (2)
H3A	0.1749	−0.1219	0.8868	0.018*
H3B	0.2931	−0.0583	0.9382	0.018*
C4	0.24219 (15)	−0.00022 (9)	0.80244 (8)	0.01321 (19)
C5	0.24938 (13)	0.11553 (8)	0.81616 (8)	0.01206 (19)
C6	0.25713 (15)	0.17857 (9)	0.73871 (8)	0.0149 (2)
C7	0.25656 (15)	0.28915 (9)	0.74601 (8)	0.0148 (2)
C8	0.25181 (14)	0.33614 (8)	0.84122 (7)	0.01221 (19)
C9	0.25195 (13)	0.27427 (8)	0.92386 (7)	0.01059 (18)
C10	0.26085 (13)	0.15838 (8)	0.91835 (8)	0.01090 (18)
C11	0.25257 (14)	0.32476 (8)	1.01300 (8)	0.01188 (19)
C12	0.24742 (13)	0.43145 (8)	1.01841 (7)	0.01168 (19)
C13	0.24969 (14)	0.49232 (9)	0.93547 (8)	0.01231 (19)
C14	0.25199 (14)	0.44240 (9)	0.84711 (8)	0.0138 (2)
H14A	0.2537	0.4803	0.7903	0.017*
C15	0.24938 (15)	0.60771 (8)	0.94329 (8)	0.0140 (2)
H15A	0.3063	0.6260	0.9999	0.017*
C16	0.3149 (2)	0.65916 (11)	0.85549 (11)	0.0284 (3)
H16A	0.4040	0.6281	0.8413	0.043*
H16B	0.3287	0.7300	0.8690	0.043*
H16C	0.2533	0.6519	0.8008	0.043*
C17	0.09920 (15)	0.64681 (10)	0.96124 (11)	0.0208 (3)
H17A	0.1012	0.7192	0.9692	0.031*
H17B	0.0620	0.6159	1.0188	0.031*
H17C	0.0406	0.6297	0.9070	0.031*
C18	0.12286 (15)	−0.02886 (11)	0.73086 (10)	0.0202 (3)
H18A	0.1413	0.0014	0.6689	0.030*
H18B	0.0345	−0.0044	0.7553	0.030*
H18C	0.1189	−0.1013	0.7241	0.030*
C19	0.38326 (14)	−0.04045 (10)	0.76210 (10)	0.0184 (2)
H19A	0.4574	−0.0258	0.8072	0.028*
H19B	0.4032	−0.0080	0.7014	0.028*
H19C	0.3768	−0.1125	0.7526	0.028*
C20	0.41271 (13)	0.13255 (10)	0.95434 (9)	0.0154 (2)
H20A	0.4805	0.1608	0.9104	0.023*
H20B	0.4242	0.0602	0.9570	0.023*
H20C	0.4267	0.1608	1.0177	0.023*

	U11	U22	U33	U12	U13	U23
O1	0.0436 (6)	0.0122 (4)	0.0090 (3)	0.0012 (5)	0.0006 (4)	−0.0013 (3)
O2	0.0489 (6)	0.0129 (4)	0.0097 (3)	0.0008 (5)	0.0007 (4)	0.0023 (3)
O3	0.0266 (4)	0.0104 (4)	0.0090 (3)	−0.0009 (4)	0.0012 (3)	−0.0018 (3)
O4	0.0305 (5)	0.0127 (4)	0.0081 (3)	0.0004 (4)	−0.0006 (4)	0.0015 (3)
C1	0.0209 (5)	0.0107 (5)	0.0166 (5)	−0.0020 (4)	0.0060 (4)	0.0002 (4)
C2	0.0184 (5)	0.0138 (5)	0.0183 (5)	−0.0026 (4)	0.0044 (4)	−0.0001 (4)
C3	0.0205 (5)	0.0093 (5)	0.0160 (5)	−0.0002 (4)	0.0013 (4)	0.0009 (4)
C4	0.0177 (5)	0.0087 (4)	0.0132 (4)	0.0010 (4)	−0.0008 (4)	−0.0007 (3)
C5	0.0156 (5)	0.0094 (4)	0.0112 (4)	0.0009 (5)	−0.0005 (4)	−0.0001 (3)
C6	0.0245 (5)	0.0103 (5)	0.0100 (4)	0.0006 (5)	−0.0002 (4)	−0.0013 (3)
C7	0.0248 (6)	0.0100 (4)	0.0096 (4)	0.0009 (5)	−0.0003 (4)	0.0003 (3)
C8	0.0179 (5)	0.0098 (4)	0.0089 (4)	0.0006 (5)	−0.0001 (4)	0.0001 (3)
C9	0.0141 (4)	0.0084 (4)	0.0093 (4)	0.0002 (4)	0.0002 (4)	0.0002 (3)
C10	0.0140 (4)	0.0088 (4)	0.0100 (4)	0.0003 (4)	−0.0003 (4)	0.0007 (3)
C11	0.0160 (5)	0.0105 (4)	0.0091 (4)	0.0000 (5)	0.0000 (4)	0.0006 (3)
C12	0.0152 (5)	0.0104 (4)	0.0095 (4)	0.0006 (5)	0.0001 (4)	−0.0011 (3)
C13	0.0167 (4)	0.0097 (4)	0.0106 (4)	0.0003 (4)	0.0001 (4)	0.0003 (3)
C14	0.0217 (5)	0.0095 (4)	0.0100 (4)	−0.0001 (5)	0.0002 (4)	0.0001 (3)
C15	0.0223 (5)	0.0077 (4)	0.0121 (4)	0.0001 (5)	0.0018 (4)	0.0000 (3)
C16	0.0519 (10)	0.0117 (5)	0.0215 (6)	0.0005 (6)	0.0146 (6)	0.0016 (5)
C17	0.0232 (6)	0.0134 (5)	0.0259 (6)	0.0024 (5)	−0.0017 (5)	−0.0024 (5)
C18	0.0257 (6)	0.0155 (6)	0.0194 (5)	−0.0024 (5)	−0.0048 (5)	−0.0027 (5)
C19	0.0232 (6)	0.0130 (5)	0.0189 (5)	0.0031 (5)	0.0045 (5)	−0.0007 (4)
C20	0.0164 (5)	0.0130 (5)	0.0168 (5)	0.0017 (4)	−0.0034 (4)	−0.0003 (4)

O1—C6	1.3733 (14)	C9—C11	1.3993 (15)
O1—H1O1	0.86 (2)	C9—C10	1.5307 (16)
O2—C7	1.2490 (14)	C10—C20	1.5626 (17)
O3—C12	1.3645 (13)	C11—C12	1.4081 (15)
O3—H1O3	0.8200	C12—C13	1.3984 (15)
O4—C11	1.3685 (13)	C13—C14	1.3864 (15)
O4—H1O4	0.81 (2)	C13—C15	1.5237 (16)
C1—C2	1.5268 (18)	C14—H14A	0.9300
C1—C10	1.5619 (17)	C15—C16	1.5222 (18)
C1—H1A	0.9700	C15—C17	1.5362 (19)
C1—H1B	0.9700	C15—H15A	0.9800
C2—C3	1.5242 (18)	C16—H16A	0.9600
C2—H2A	0.9700	C16—H16B	0.9600
C2—H2B	0.9700	C16—H16C	0.9600
C3—C4	1.5462 (17)	C17—H17A	0.9600
C3—H3A	0.9700	C17—H17B	0.9600
C3—H3B	0.9700	C17—H17C	0.9600
C4—C5	1.5378 (16)	C18—H18A	0.9600
C4—C19	1.5444 (19)	C18—H18B	0.9600
C4—C18	1.5504 (18)	C18—H18C	0.9600
C5—C6	1.3562 (16)	C19—H19A	0.9600
C5—C10	1.5240 (15)	C19—H19B	0.9600
C6—C7	1.4600 (16)	C19—H19C	0.9600
C7—C8	1.4542 (15)	C20—H20A	0.9600
C8—C14	1.4020 (15)	C20—H20B	0.9600
C8—C9	1.4025 (14)	C20—H20C	0.9600
C6—O1—H1O1	103.0 (15)	O4—C11—C9	121.14 (10)
C12—O3—H1O3	109.5	O4—C11—C12	117.47 (9)
C11—O4—H1O4	99.1 (16)	C9—C11—C12	121.39 (10)
C2—C1—C10	114.88 (10)	O3—C12—C13	125.37 (10)
C2—C1—H1A	108.5	O3—C12—C11	112.74 (9)
C10—C1—H1A	108.5	C13—C12—C11	121.88 (10)
C2—C1—H1B	108.5	C14—C13—C12	116.71 (10)
C10—C1—H1B	108.5	C14—C13—C15	122.37 (10)
H1A—C1—H1B	107.5	C12—C13—C15	120.91 (10)
C3—C2—C1	112.14 (11)	C13—C14—C8	121.63 (10)
C3—C2—H2A	109.2	C13—C14—H14A	119.2
C1—C2—H2A	109.2	C8—C14—H14A	119.2
C3—C2—H2B	109.2	C16—C15—C13	112.76 (10)
C1—C2—H2B	109.2	C16—C15—C17	111.02 (12)
H2A—C2—H2B	107.9	C13—C15—C17	110.34 (11)
C2—C3—C4	110.58 (10)	C16—C15—H15A	107.5
C2—C3—H3A	109.5	C13—C15—H15A	107.5
C4—C3—H3A	109.5	C17—C15—H15A	107.5
C2—C3—H3B	109.5	C15—C16—H16A	109.5
C4—C3—H3B	109.5	C15—C16—H16B	109.5
H3A—C3—H3B	108.1	H16A—C16—H16B	109.5
C5—C4—C19	110.25 (11)	C15—C16—H16C	109.5
C5—C4—C3	110.69 (9)	H16A—C16—H16C	109.5
C19—C4—C3	109.72 (10)	H16B—C16—H16C	109.5
C5—C4—C18	110.63 (10)	C15—C17—H17A	109.5
C19—C4—C18	108.68 (10)	C15—C17—H17B	109.5
C3—C4—C18	106.80 (10)	H17A—C17—H17B	109.5
C6—C5—C10	119.99 (10)	C15—C17—H17C	109.5
C6—C5—C4	120.81 (10)	H17A—C17—H17C	109.5
C10—C5—C4	118.97 (9)	H17B—C17—H17C	109.5
C5—C6—O1	123.23 (11)	C4—C18—H18A	109.5
C5—C6—C7	123.79 (10)	C4—C18—H18B	109.5
O1—C6—C7	112.98 (10)	H18A—C18—H18B	109.5
O2—C7—C8	124.11 (10)	C4—C18—H18C	109.5
O2—C7—C6	116.73 (10)	H18A—C18—H18C	109.5
C8—C7—C6	119.15 (10)	H18B—C18—H18C	109.5
C14—C8—C9	122.20 (10)	C4—C19—H19A	109.5
C14—C8—C7	118.51 (10)	C4—C19—H19B	109.5
C9—C8—C7	119.25 (10)	H19A—C19—H19B	109.5
C11—C9—C8	116.10 (10)	C4—C19—H19C	109.5
C11—C9—C10	121.16 (9)	H19A—C19—H19C	109.5
C8—C9—C10	122.62 (9)	H19B—C19—H19C	109.5
C5—C10—C9	114.30 (9)	C10—C20—H20A	109.5
C5—C10—C1	110.80 (10)	C10—C20—H20B	109.5
C9—C10—C1	109.83 (9)	H20A—C20—H20B	109.5
C5—C10—C20	106.26 (10)	C10—C20—H20C	109.5
C9—C10—C20	104.61 (10)	H20A—C20—H20C	109.5
C1—C10—C20	110.81 (9)	H20B—C20—H20C	109.5
C10—C1—C2—C3	29.06 (15)	C6—C5—C10—C20	−103.51 (13)
C1—C2—C3—C4	−65.02 (14)	C4—C5—C10—C20	71.15 (14)
C2—C3—C4—C5	41.24 (14)	C11—C9—C10—C5	176.26 (11)
C2—C3—C4—C19	163.14 (10)	C8—C9—C10—C5	−7.91 (17)
C2—C3—C4—C18	−79.24 (12)	C11—C9—C10—C1	51.02 (15)
C19—C4—C5—C6	68.23 (16)	C8—C9—C10—C1	−133.15 (12)
C3—C4—C5—C6	−170.18 (12)	C11—C9—C10—C20	−67.95 (14)
C18—C4—C5—C6	−52.01 (17)	C8—C9—C10—C20	107.89 (13)
C19—C4—C5—C10	−106.38 (12)	C2—C1—C10—C5	25.02 (15)
C3—C4—C5—C10	15.20 (16)	C2—C1—C10—C9	152.24 (11)
C18—C4—C5—C10	133.38 (11)	C2—C1—C10—C20	−92.68 (13)
C10—C5—C6—O1	171.98 (12)	C8—C9—C11—O4	−177.87 (12)
C4—C5—C6—O1	−2.6 (2)	C10—C9—C11—O4	−1.77 (19)
C10—C5—C6—C7	−8.9 (2)	C8—C9—C11—C12	2.54 (19)
C4—C5—C6—C7	176.56 (13)	C10—C9—C11—C12	178.63 (11)
C5—C6—C7—O2	−177.17 (14)	O4—C11—C12—O3	−2.26 (19)
O1—C6—C7—O2	2.0 (2)	C9—C11—C12—O3	177.35 (11)
C5—C6—C7—C8	2.0 (2)	O4—C11—C12—C13	176.62 (11)
O1—C6—C7—C8	−178.82 (12)	C9—C11—C12—C13	−3.8 (2)
O2—C7—C8—C14	−1.2 (2)	O3—C12—C13—C14	−178.94 (13)
C6—C7—C8—C14	179.71 (13)	C11—C12—C13—C14	2.33 (19)
O2—C7—C8—C9	−179.12 (14)	O3—C12—C13—C15	1.0 (2)
C6—C7—C8—C9	1.8 (2)	C11—C12—C13—C15	−177.76 (12)
C14—C8—C9—C11	−0.13 (19)	C12—C13—C14—C8	0.1 (2)
C7—C8—C9—C11	177.69 (12)	C15—C13—C14—C8	−179.81 (13)
C14—C8—C9—C10	−176.16 (12)	C9—C8—C14—C13	−1.2 (2)
C7—C8—C9—C10	1.66 (19)	C7—C8—C14—C13	−179.04 (12)
C6—C5—C10—C9	11.32 (18)	C14—C13—C15—C16	−25.4 (2)
C4—C5—C10—C9	−174.02 (10)	C12—C13—C15—C16	154.74 (13)
C6—C5—C10—C1	136.05 (13)	C14—C13—C15—C17	99.41 (15)
C4—C5—C10—C1	−49.30 (15)	C12—C13—C15—C17	−80.49 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.86 (2)	1.97 (2)	2.5626 (13)	124.5 (19)
O3—H1O3···O2i	0.82	1.93	2.7008 (13)	156
O4—H1O4···O3	0.81 (2)	1.96 (2)	2.5677 (13)	131 (2)
C14—H14A···O3ii	0.93	2.57	3.4712 (14)	163
C15—H15A···O2i	0.98	2.45	3.1908 (14)	132
C18—H18A···O1	0.96	2.24	2.9053 (18)	125
C19—H19B···O1	0.96	2.53	3.1360 (17)	121
C20—H20C···O4	0.96	2.44	3.0838 (16)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.86 (2)	1.97 (2)	2.5626 (13)	124.5 (19)
O3—H1O3⋯O2i	0.82	1.93	2.7008 (13)	156
O4—H1O4⋯O3	0.81 (2)	1.96 (2)	2.5677 (13)	131 (2)
C14—H14A⋯O3ii	0.93	2.57	3.4712 (14)	163
C15—H15A⋯O2i	0.98	2.45	3.1908 (14)	132
C18—H18A⋯O1	0.96	2.24	2.9053 (18)	125
C19—H19B⋯O1	0.96	2.53	3.1360 (17)	121
C20—H20C⋯O4	0.96	2.44	3.0838 (16)	124

Symmetry codes: (i) ; (ii) .