6α-Hy-droxy-5,6-dihydro-salviasperanol.

In the title compound, C(20)H(28)O(4), a diterpenoid isolated from the roots of Premna obtusifolia (Verbenaceae), the five-membered ring is in a half-chair conformation. One six-membered ring exists in a twisted-boat conformation while the other is in half-boat conformation. The crystal packing is stabilized by inter-molecular O-H⋯O and weak C-H⋯O inter-actions, generating (001) sheets.

Related literature

For background to Verbenaceae, diterpenes and their bio­log­ical activity, see: Hymavathi et al. (2009 ▶); Bunluepuech & Tewtrakul (2009 ▶); Esquivel et al. (1995 ▶). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H28O4

M = 332.42

Orthorhombic,

a = 6.2767 (2) Å

b = 11.7358 (4) Å

c = 23.7496 (7) Å

V = 1749.45 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.49 × 0.36 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005) T min = 0.959, T max = 0.979

15028 measured reflections

3534 independent reflections

3079 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.15

3534 reflections

233 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S160053681004208X/hb5689sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004208X/hb5689Isup2.hkl

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

C20H28O4	F(000) = 720
Mr = 332.42	Dx = 1.262 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6222 reflections
a = 6.2767 (2) Å	θ = 2.4–32.3°
b = 11.7358 (4) Å	µ = 0.09 mm−1
c = 23.7496 (7) Å	T = 100 K
V = 1749.45 (10) Å3	Block, colourless
Z = 4	0.49 × 0.36 × 0.24 mm

Bruker SMART APEXII CCD area-detector diffractometer	3534 independent reflections
Radiation source: sealed tube	3079 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 32.4°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→9
Tmin = 0.959, Tmax = 0.979	k = −17→16
15028 measured reflections	l = −34→35

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.2019P] where P = (Fo2 + 2Fc2)/3
3534 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.25 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.7000 (2)	0.51248 (9)	0.29871 (5)	0.0162 (2)
O2	0.3927 (2)	0.76867 (10)	0.28241 (5)	0.0179 (2)
H1O2	0.295 (4)	0.730 (2)	0.2677 (10)	0.035 (7)*
O3	−0.1349 (2)	0.42654 (11)	0.15694 (5)	0.0212 (3)
H1O3	−0.199 (5)	0.379 (2)	0.1782 (10)	0.036 (7)*
O4	−0.0204 (2)	0.35135 (9)	0.26393 (5)	0.0175 (2)
H1O4	−0.122 (5)	0.391 (2)	0.2762 (10)	0.034 (7)*
C1	0.6494 (3)	0.43356 (13)	0.39056 (7)	0.0193 (3)
H1A	0.7202	0.3676	0.3746	0.023*
H1B	0.5407	0.4058	0.4162	0.023*
C2	0.8142 (3)	0.50212 (15)	0.42483 (7)	0.0231 (3)
H2A	0.8018	0.4811	0.4642	0.028*
H2B	0.9560	0.4811	0.4124	0.028*
C3	0.7889 (3)	0.63252 (15)	0.41961 (7)	0.0200 (3)
H3A	0.8483	0.6684	0.4529	0.024*
H3B	0.8699	0.6588	0.3873	0.024*
C4	0.5563 (3)	0.67027 (13)	0.41290 (6)	0.0162 (3)
C5	0.4707 (3)	0.62326 (12)	0.35629 (6)	0.0141 (3)
H5A	0.3147	0.6257	0.3574	0.017*
C6	0.5467 (3)	0.69065 (12)	0.30370 (6)	0.0141 (3)
H6A	0.6753	0.7334	0.3138	0.017*
C7	0.6093 (3)	0.59624 (12)	0.26148 (6)	0.0146 (3)
H7A	0.7152	0.6239	0.2344	0.018*
C8	0.4169 (3)	0.54859 (12)	0.23181 (6)	0.0145 (3)
C9	0.2902 (3)	0.47081 (12)	0.26130 (6)	0.0144 (3)
C10	0.5406 (3)	0.49841 (12)	0.34320 (6)	0.0147 (3)
C11	0.1059 (3)	0.43033 (12)	0.23603 (6)	0.0145 (3)
C12	0.0464 (3)	0.46583 (13)	0.18190 (6)	0.0155 (3)
C13	0.1739 (3)	0.54262 (13)	0.15161 (6)	0.0161 (3)
C14	0.3583 (3)	0.58331 (12)	0.17780 (6)	0.0154 (3)
H14A	0.4443	0.6350	0.1587	0.018*
C15	0.1063 (3)	0.57665 (14)	0.09244 (6)	0.0196 (3)
H15A	0.0468	0.5085	0.0745	0.023*
C16	0.2922 (3)	0.61702 (16)	0.05555 (7)	0.0237 (4)
H16A	0.2431	0.6281	0.0177	0.036*
H16B	0.4030	0.5606	0.0559	0.036*
H16C	0.3468	0.6876	0.0700	0.036*
C17	−0.0714 (3)	0.66608 (18)	0.09427 (8)	0.0286 (4)
H17A	−0.1905	0.6364	0.1150	0.043*
H17B	−0.1153	0.6841	0.0566	0.043*
H17C	−0.0197	0.7338	0.1124	0.043*
C18	0.5432 (3)	0.80127 (14)	0.41448 (7)	0.0205 (3)
H18A	0.5862	0.8280	0.4510	0.031*
H18B	0.3994	0.8248	0.4072	0.031*
H18C	0.6359	0.8326	0.3863	0.031*
C19	0.4188 (3)	0.62608 (15)	0.46181 (6)	0.0213 (3)
H19A	0.4798	0.6501	0.4969	0.032*
H19B	0.4136	0.5444	0.4606	0.032*
H19C	0.2771	0.6561	0.4585	0.032*
C20	0.3572 (3)	0.42821 (12)	0.31863 (6)	0.0158 (3)
H20A	0.4012	0.3492	0.3156	0.019*
H20B	0.2363	0.4316	0.3440	0.019*

	U11	U22	U33	U12	U13	U23
O1	0.0152 (6)	0.0138 (5)	0.0197 (5)	0.0030 (4)	0.0026 (4)	0.0022 (4)
O2	0.0206 (6)	0.0119 (5)	0.0213 (5)	0.0033 (5)	−0.0016 (5)	0.0015 (4)
O3	0.0204 (7)	0.0206 (5)	0.0226 (5)	−0.0081 (5)	−0.0026 (5)	0.0026 (4)
O4	0.0182 (6)	0.0109 (5)	0.0234 (5)	−0.0024 (4)	0.0037 (5)	0.0006 (4)
C1	0.0231 (9)	0.0138 (6)	0.0211 (6)	0.0039 (6)	−0.0016 (6)	0.0029 (5)
C2	0.0221 (9)	0.0215 (8)	0.0257 (7)	0.0055 (7)	−0.0053 (7)	0.0015 (6)
C3	0.0194 (8)	0.0193 (7)	0.0214 (7)	−0.0001 (7)	−0.0029 (6)	−0.0001 (6)
C4	0.0188 (8)	0.0126 (6)	0.0173 (6)	−0.0004 (6)	−0.0016 (6)	0.0002 (5)
C5	0.0145 (7)	0.0107 (6)	0.0171 (6)	0.0005 (6)	0.0002 (5)	0.0004 (5)
C6	0.0144 (7)	0.0111 (6)	0.0168 (6)	0.0006 (6)	−0.0005 (5)	−0.0001 (5)
C7	0.0153 (7)	0.0120 (6)	0.0165 (6)	0.0000 (6)	0.0008 (5)	0.0015 (5)
C8	0.0147 (8)	0.0115 (6)	0.0174 (6)	0.0003 (5)	0.0014 (5)	−0.0010 (5)
C9	0.0162 (7)	0.0102 (6)	0.0168 (6)	0.0009 (5)	0.0023 (6)	−0.0011 (5)
C10	0.0139 (7)	0.0122 (6)	0.0180 (6)	0.0007 (6)	0.0007 (5)	0.0013 (5)
C11	0.0161 (7)	0.0086 (5)	0.0189 (6)	−0.0002 (5)	0.0037 (5)	−0.0002 (5)
C12	0.0146 (8)	0.0120 (6)	0.0198 (6)	−0.0009 (6)	0.0003 (6)	−0.0019 (5)
C13	0.0184 (8)	0.0130 (6)	0.0168 (6)	0.0008 (6)	0.0011 (6)	−0.0012 (5)
C14	0.0169 (8)	0.0118 (6)	0.0174 (6)	−0.0009 (6)	0.0027 (5)	−0.0009 (5)
C15	0.0236 (9)	0.0180 (7)	0.0171 (6)	−0.0057 (7)	−0.0017 (6)	0.0002 (5)
C16	0.0324 (10)	0.0202 (7)	0.0186 (6)	−0.0058 (8)	0.0027 (7)	−0.0002 (6)
C17	0.0235 (10)	0.0304 (9)	0.0318 (8)	0.0020 (8)	−0.0039 (7)	0.0089 (7)
C18	0.0269 (9)	0.0144 (6)	0.0203 (6)	0.0009 (7)	−0.0026 (7)	−0.0020 (5)
C19	0.0262 (9)	0.0206 (7)	0.0171 (6)	0.0005 (7)	0.0028 (6)	0.0013 (6)
C20	0.0193 (8)	0.0100 (6)	0.0181 (6)	−0.0015 (6)	0.0011 (6)	0.0006 (5)

O1—C7	1.4395 (18)	C8—C14	1.395 (2)
O1—C10	1.4647 (19)	C8—C9	1.399 (2)
O2—C6	1.4244 (19)	C9—C11	1.387 (2)
O2—H1O2	0.84 (3)	C9—C20	1.510 (2)
O3—C12	1.363 (2)	C10—C20	1.531 (2)
O3—H1O3	0.85 (3)	C11—C12	1.402 (2)
O4—C11	1.3882 (18)	C12—C13	1.404 (2)
O4—H1O4	0.84 (3)	C13—C14	1.398 (2)
C1—C10	1.520 (2)	C13—C15	1.521 (2)
C1—C2	1.543 (3)	C14—H14A	0.9300
C1—H1A	0.9700	C15—C17	1.532 (3)
C1—H1B	0.9700	C15—C16	1.534 (2)
C2—C3	1.544 (2)	C15—H15A	0.9800
C2—H2A	0.9700	C16—H16A	0.9600
C2—H2B	0.9700	C16—H16B	0.9600
C3—C4	1.535 (3)	C16—H16C	0.9600
C3—H3A	0.9700	C17—H17A	0.9600
C3—H3B	0.9700	C17—H17B	0.9600
C4—C19	1.537 (2)	C17—H17C	0.9600
C4—C18	1.540 (2)	C18—H18A	0.9600
C4—C5	1.549 (2)	C18—H18B	0.9600
C5—C6	1.553 (2)	C18—H18C	0.9600
C5—C10	1.561 (2)	C19—H19A	0.9600
C5—H5A	0.9800	C19—H19B	0.9600
C6—C7	1.545 (2)	C19—H19C	0.9600
C6—H6A	0.9800	C20—H20A	0.9700
C7—C8	1.506 (2)	C20—H20B	0.9700
C7—H7A	0.9800
C7—O1—C10	104.47 (12)	O1—C10—C20	107.42 (12)
C6—O2—H1O2	107.5 (18)	C1—C10—C20	110.51 (12)
C12—O3—H1O3	110.8 (18)	O1—C10—C5	103.28 (11)
C11—O4—H1O4	103.5 (18)	C1—C10—C5	116.68 (12)
C10—C1—C2	115.50 (13)	C20—C10—C5	111.72 (13)
C10—C1—H1A	108.4	C9—C11—O4	119.91 (13)
C2—C1—H1A	108.4	C9—C11—C12	121.15 (14)
C10—C1—H1B	108.4	O4—C11—C12	118.93 (14)
C2—C1—H1B	108.4	O3—C12—C11	121.38 (14)
H1A—C1—H1B	107.5	O3—C12—C13	118.05 (13)
C3—C2—C1	113.94 (14)	C11—C12—C13	120.57 (15)
C3—C2—H2A	108.8	C14—C13—C12	117.61 (14)
C1—C2—H2A	108.8	C14—C13—C15	123.51 (14)
C3—C2—H2B	108.8	C12—C13—C15	118.88 (15)
C1—C2—H2B	108.8	C8—C14—C13	121.84 (14)
H2A—C2—H2B	107.7	C8—C14—H14A	119.1
C4—C3—C2	113.11 (15)	C13—C14—H14A	119.1
C4—C3—H3A	109.0	C13—C15—C17	110.89 (14)
C2—C3—H3A	109.0	C13—C15—C16	113.37 (15)
C4—C3—H3B	109.0	C17—C15—C16	111.00 (15)
C2—C3—H3B	109.0	C13—C15—H15A	107.1
H3A—C3—H3B	107.8	C17—C15—H15A	107.1
C3—C4—C19	111.00 (13)	C16—C15—H15A	107.1
C3—C4—C18	109.66 (15)	C15—C16—H16A	109.5
C19—C4—C18	106.77 (14)	C15—C16—H16B	109.5
C3—C4—C5	108.49 (13)	H16A—C16—H16B	109.5
C19—C4—C5	109.94 (14)	C15—C16—H16C	109.5
C18—C4—C5	110.99 (13)	H16A—C16—H16C	109.5
C4—C5—C6	114.20 (12)	H16B—C16—H16C	109.5
C4—C5—C10	114.19 (13)	C15—C17—H17A	109.5
C6—C5—C10	103.40 (11)	C15—C17—H17B	109.5
C4—C5—H5A	108.3	H17A—C17—H17B	109.5
C6—C5—H5A	108.3	C15—C17—H17C	109.5
C10—C5—H5A	108.3	H17A—C17—H17C	109.5
O2—C6—C7	113.77 (12)	H17B—C17—H17C	109.5
O2—C6—C5	113.85 (13)	C4—C18—H18A	109.5
C7—C6—C5	103.57 (11)	C4—C18—H18B	109.5
O2—C6—H6A	108.5	H18A—C18—H18B	109.5
C7—C6—H6A	108.5	C4—C18—H18C	109.5
C5—C6—H6A	108.5	H18A—C18—H18C	109.5
O1—C7—C8	110.55 (12)	H18B—C18—H18C	109.5
O1—C7—C6	101.05 (11)	C4—C19—H19A	109.5
C8—C7—C6	111.48 (13)	C4—C19—H19B	109.5
O1—C7—H7A	111.1	H19A—C19—H19B	109.5
C8—C7—H7A	111.1	C4—C19—H19C	109.5
C6—C7—H7A	111.1	H19A—C19—H19C	109.5
C14—C8—C9	120.06 (15)	H19B—C19—H19C	109.5
C14—C8—C7	122.22 (13)	C9—C20—C10	112.02 (12)
C9—C8—C7	117.66 (13)	C9—C20—H20A	109.2
C11—C9—C8	118.76 (14)	C10—C20—H20A	109.2
C11—C9—C20	120.60 (14)	C9—C20—H20B	109.2
C8—C9—C20	120.59 (14)	C10—C20—H20B	109.2
O1—C10—C1	106.44 (13)	H20A—C20—H20B	107.9
C10—C1—C2—C3	19.7 (2)	C2—C1—C10—C20	−171.02 (14)
C1—C2—C3—C4	33.4 (2)	C2—C1—C10—C5	−42.0 (2)
C2—C3—C4—C19	56.16 (18)	C4—C5—C10—O1	−106.69 (14)
C2—C3—C4—C18	173.89 (13)	C6—C5—C10—O1	17.99 (15)
C2—C3—C4—C5	−64.74 (16)	C4—C5—C10—C1	9.7 (2)
C3—C4—C5—C6	−77.19 (16)	C6—C5—C10—C1	134.36 (14)
C19—C4—C5—C6	161.26 (14)	C4—C5—C10—C20	138.16 (14)
C18—C4—C5—C6	43.4 (2)	C6—C5—C10—C20	−97.16 (14)
C3—C4—C5—C10	41.52 (17)	C8—C9—C11—O4	178.72 (13)
C19—C4—C5—C10	−80.04 (17)	C20—C9—C11—O4	1.1 (2)
C18—C4—C5—C10	162.07 (14)	C8—C9—C11—C12	0.2 (2)
C4—C5—C6—O2	−100.27 (16)	C20—C9—C11—C12	−177.48 (14)
C10—C5—C6—O2	135.06 (13)	C9—C11—C12—O3	−179.81 (14)
C4—C5—C6—C7	135.67 (14)	O4—C11—C12—O3	1.6 (2)
C10—C5—C6—C7	11.00 (16)	C9—C11—C12—C13	0.7 (2)
C10—O1—C7—C8	−67.98 (14)	O4—C11—C12—C13	−177.83 (14)
C10—O1—C7—C6	50.16 (14)	O3—C12—C13—C14	179.36 (14)
O2—C6—C7—O1	−160.80 (13)	C11—C12—C13—C14	−1.2 (2)
C5—C6—C7—O1	−36.69 (15)	O3—C12—C13—C15	−1.0 (2)
O2—C6—C7—C8	−43.34 (17)	C11—C12—C13—C15	178.49 (14)
C5—C6—C7—C8	80.77 (14)	C9—C8—C14—C13	0.1 (2)
O1—C7—C8—C14	−149.31 (14)	C7—C8—C14—C13	−176.94 (14)
C6—C7—C8—C14	99.13 (16)	C12—C13—C14—C8	0.8 (2)
O1—C7—C8—C9	33.56 (18)	C15—C13—C14—C8	−178.89 (15)
C6—C7—C8—C9	−77.99 (16)	C14—C13—C15—C17	−101.80 (19)
C14—C8—C9—C11	−0.6 (2)	C12—C13—C15—C17	78.55 (19)
C7—C8—C9—C11	176.60 (13)	C14—C13—C15—C16	23.9 (2)
C14—C8—C9—C20	177.05 (14)	C12—C13—C15—C16	−155.80 (15)
C7—C8—C9—C20	−5.8 (2)	C11—C9—C20—C10	−169.78 (14)
C7—O1—C10—C1	−166.58 (12)	C8—C9—C20—C10	12.6 (2)
C7—O1—C10—C20	75.03 (13)	O1—C10—C20—C9	−46.44 (16)
C7—O1—C10—C5	−43.17 (14)	C1—C10—C20—C9	−162.17 (13)
C2—C1—C10—O1	72.64 (16)	C5—C10—C20—C9	66.15 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O2i	0.85 (3)	2.01 (3)	2.8504 (17)	169 (3)
O4—H1O4···O1ii	0.84 (3)	1.89 (3)	2.7089 (16)	165 (3)
C18—H18B···O3iii	0.96	2.55	3.407 (2)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O2i	0.85 (3)	2.01 (3)	2.8504 (17)	169 (3)
O4—H1O4⋯O1ii	0.84 (3)	1.89 (3)	2.7089 (16)	165 (3)
C18—H18B⋯O3iii	0.96	2.55	3.407 (2)	149

Symmetry codes: (i) ; (ii) ; (iii) .