ent-5α,3,15-Dioxodolabr-4(18)-ene-16,18-diol.

The title compound, C(20)H(30)O(4), is a dolabrane diterpenoid isolated from Ceriops tagal, in which one of the three fused cyclo-hexane rings adopts a half-chair conformation and the other two are in the standard chair conformations. The hy-droxy-methyl-idene substituent is attached to the half-chair cyclo-hexane. An intra-molecular O-H⋯O hydrogen bond generate an S(6) ring motif. In the crystal, mol-ecules are arranged into screw chains along the [001] direction. The crystal is stabilized by O-H⋯O hydrogen bonds and weaker C-H⋯O inter-actions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For background to diterpenoids, see, for example: Hu et al. (2010 ▶); Zhang et al. (2005 ▶). For related structures, see: Chantrapromma et al. (2007 ▶); Fun et al. (2006 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C20H30O4

M = 334.44

Orthorhombic,

a = 7.9633 (3) Å

b = 10.7166 (4) Å

c = 20.8338 (7) Å

V = 1777.95 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.58 × 0.51 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.952, T max = 0.992

20568 measured reflections

2691 independent reflections

2084 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.157

S = 1.09

2691 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.45 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/S1600536810042078/fj2353sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042078/fj2353Isup2.hkl

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

C20H30O4	Dx = 1.249 Mg m−3
Mr = 334.44	Melting point = 495–496 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2691 reflections
a = 7.9633 (3) Å	θ = 2.0–29.0°
b = 10.7166 (4) Å	µ = 0.09 mm−1
c = 20.8338 (7) Å	T = 100 K
V = 1777.95 (11) Å3	Plate, colourless
Z = 4	0.58 × 0.51 × 0.10 mm
F(000) = 728

Bruker APEXII CCD area-detector diffractometer	2691 independent reflections
Radiation source: sealed tube	2084 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 29.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
Tmin = 0.952, Tmax = 0.992	k = −14→10
20568 measured reflections	l = −24→28

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.077P)2 + 0.7994P] where P = (Fo2 + 2Fc2)/3
2691 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.44 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	0.9767 (3)	0.4254 (2)	0.05460 (11)	0.0420 (6)
O2	1.2362 (4)	0.3517 (3)	0.10215 (15)	0.0633 (8)
H1O2	1.1724	0.3988	0.0830	0.095*
O3	0.5983 (4)	0.4271 (2)	0.41250 (10)	0.0413 (6)
O4	0.6697 (4)	0.3378 (2)	0.52946 (11)	0.0552 (8)
H1O4	0.6102	0.4000	0.5273	0.083*
C1	0.6196 (4)	0.2200 (3)	0.09423 (15)	0.0360 (8)
H1A	0.5759	0.1550	0.0665	0.043*
H1B	0.5242	0.2658	0.1110	0.043*
C2	0.7243 (4)	0.3092 (3)	0.05327 (15)	0.0379 (8)
H2A	0.7218	0.2792	0.0094	0.045*
H2B	0.6696	0.3900	0.0537	0.045*
C3	0.9026 (4)	0.3276 (3)	0.07172 (13)	0.0294 (7)
C4	0.9885 (3)	0.2325 (3)	0.10845 (12)	0.0221 (5)
C5	0.8927 (4)	0.1186 (3)	0.13108 (13)	0.0230 (6)
C6	0.9782 (4)	0.0532 (3)	0.18765 (13)	0.0301 (7)
H6A	0.9239	−0.0267	0.1947	0.036*
H6B	1.0944	0.0370	0.1765	0.036*
C7	0.9731 (4)	0.1276 (3)	0.24997 (14)	0.0272 (6)
H7A	1.0337	0.2054	0.2446	0.033*
H7B	1.0269	0.0805	0.2840	0.033*
C8	0.7911 (4)	0.1547 (2)	0.26801 (13)	0.0226 (6)
H8A	0.7344	0.0737	0.2708	0.027*
C9	0.6987 (3)	0.2298 (2)	0.21580 (13)	0.0200 (5)
C10	0.7108 (4)	0.1569 (3)	0.15117 (13)	0.0241 (6)
H10A	0.6510	0.0783	0.1585	0.029*
C11	0.5122 (4)	0.2385 (3)	0.23683 (14)	0.0318 (7)
H11A	0.4514	0.2889	0.2059	0.038*
H11B	0.4636	0.1555	0.2363	0.038*
C12	0.4884 (4)	0.2955 (3)	0.30434 (14)	0.0338 (7)
H12A	0.5200	0.3828	0.3030	0.041*
H12B	0.3705	0.2912	0.3157	0.041*
C13	0.5915 (4)	0.2302 (3)	0.35673 (14)	0.0276 (6)
C14	0.7769 (4)	0.2146 (2)	0.33451 (13)	0.0227 (6)
H14A	0.8305	0.2958	0.3336	0.027*
H14B	0.8364	0.1633	0.3654	0.027*
C15	0.6017 (4)	0.3139 (3)	0.41616 (14)	0.0290 (6)
C16	0.6242 (5)	0.2539 (3)	0.48109 (14)	0.0394 (8)
H16A	0.5201	0.2133	0.4932	0.047*
H16B	0.7100	0.1900	0.4778	0.047*
C17	0.5129 (5)	0.1042 (3)	0.37320 (18)	0.0463 (9)
H17A	0.4050	0.1172	0.3926	0.070*
H17B	0.5844	0.0603	0.4026	0.070*
H17C	0.4998	0.0559	0.3347	0.070*
C18	1.1538 (4)	0.2500 (3)	0.11951 (15)	0.0342 (7)
H18A	1.2130	0.1872	0.1404	0.041*
C19	0.8839 (5)	0.0238 (3)	0.07522 (15)	0.0352 (7)
H19A	0.9938	−0.0099	0.0674	0.053*
H19B	0.8441	0.0649	0.0372	0.053*
H19C	0.8085	−0.0427	0.0864	0.053*
C20	0.7677 (4)	0.3630 (2)	0.21044 (13)	0.0236 (6)
H20A	0.7370	0.4095	0.2480	0.035*
H20B	0.7213	0.4026	0.1731	0.035*
H20C	0.8878	0.3602	0.2068	0.035*

	U11	U22	U33	U12	U13	U23
O1	0.0564 (16)	0.0328 (12)	0.0369 (12)	0.0036 (12)	0.0098 (12)	0.0126 (10)
O2	0.0435 (16)	0.0705 (19)	0.076 (2)	−0.0151 (15)	0.0071 (15)	0.0049 (17)
O3	0.0643 (16)	0.0281 (11)	0.0314 (11)	0.0050 (12)	−0.0030 (12)	−0.0080 (10)
O4	0.088 (2)	0.0437 (14)	0.0337 (12)	0.0225 (15)	−0.0180 (13)	−0.0096 (11)
C1	0.0222 (14)	0.056 (2)	0.0301 (15)	0.0036 (14)	−0.0107 (12)	−0.0167 (15)
C2	0.0410 (19)	0.0438 (19)	0.0290 (16)	0.0139 (16)	−0.0147 (14)	−0.0040 (14)
C3	0.0375 (16)	0.0331 (16)	0.0177 (13)	0.0076 (14)	0.0011 (12)	0.0008 (12)
C4	0.0231 (13)	0.0252 (13)	0.0180 (12)	0.0007 (11)	−0.0014 (10)	−0.0005 (10)
C5	0.0233 (13)	0.0212 (13)	0.0245 (13)	0.0021 (11)	−0.0020 (11)	−0.0020 (10)
C6	0.0374 (17)	0.0228 (14)	0.0303 (14)	0.0123 (13)	0.0022 (13)	0.0022 (12)
C7	0.0310 (15)	0.0272 (14)	0.0232 (12)	0.0127 (13)	−0.0015 (12)	0.0032 (11)
C8	0.0289 (14)	0.0133 (11)	0.0254 (13)	0.0001 (11)	0.0041 (11)	0.0011 (10)
C9	0.0154 (11)	0.0198 (12)	0.0248 (13)	−0.0013 (10)	−0.0024 (10)	−0.0051 (11)
C10	0.0212 (13)	0.0241 (14)	0.0269 (14)	−0.0030 (11)	−0.0016 (11)	−0.0068 (12)
C11	0.0190 (13)	0.0440 (18)	0.0325 (16)	−0.0016 (13)	−0.0016 (11)	−0.0148 (14)
C12	0.0187 (14)	0.0483 (18)	0.0345 (15)	0.0004 (14)	0.0012 (12)	−0.0138 (14)
C13	0.0288 (14)	0.0250 (14)	0.0290 (14)	−0.0062 (13)	0.0068 (12)	−0.0070 (12)
C14	0.0293 (14)	0.0145 (12)	0.0242 (13)	0.0027 (11)	0.0002 (11)	0.0009 (10)
C15	0.0265 (14)	0.0320 (15)	0.0286 (15)	0.0014 (13)	0.0044 (12)	−0.0051 (12)
C16	0.050 (2)	0.0347 (17)	0.0333 (18)	0.0056 (17)	0.0005 (15)	−0.0039 (15)
C17	0.057 (2)	0.0367 (18)	0.0451 (19)	−0.0219 (17)	0.0195 (18)	−0.0115 (15)
C18	0.0254 (14)	0.0401 (18)	0.0372 (17)	−0.0031 (14)	−0.0048 (13)	0.0034 (15)
C19	0.0434 (19)	0.0287 (15)	0.0335 (16)	0.0018 (15)	0.0058 (15)	−0.0086 (13)
C20	0.0285 (14)	0.0170 (12)	0.0253 (13)	0.0036 (11)	−0.0081 (11)	−0.0002 (11)

O1—C3	1.254 (4)	C9—C20	1.534 (4)
O2—C18	1.323 (4)	C9—C11	1.551 (4)
O2—H1O2	0.8200	C9—C10	1.560 (4)
O3—C15	1.216 (4)	C10—H10A	0.9800
O4—C16	1.398 (4)	C11—C12	1.545 (4)
O4—H1O4	0.8200	C11—H11A	0.9700
C1—C2	1.529 (5)	C11—H11B	0.9700
C1—C10	1.547 (4)	C12—C13	1.535 (4)
C1—H1A	0.9700	C12—H12A	0.9700
C1—H1B	0.9700	C12—H12B	0.9700
C2—C3	1.484 (5)	C13—C17	1.527 (4)
C2—H2A	0.9700	C13—C15	1.531 (4)
C2—H2B	0.9700	C13—C14	1.556 (4)
C3—C4	1.446 (4)	C14—H14A	0.9700
C4—C18	1.350 (4)	C14—H14B	0.9700
C4—C5	1.515 (4)	C15—C16	1.508 (4)
C5—C6	1.531 (4)	C16—H16A	0.9700
C5—C19	1.547 (4)	C16—H16B	0.9700
C5—C10	1.563 (4)	C17—H17A	0.9600
C6—C7	1.525 (4)	C17—H17B	0.9600
C6—H6A	0.9700	C17—H17C	0.9600
C6—H6B	0.9700	C18—H18A	0.9300
C7—C8	1.525 (4)	C19—H19A	0.9600
C7—H7A	0.9700	C19—H19B	0.9600
C7—H7B	0.9700	C19—H19C	0.9600
C8—C14	1.531 (4)	C20—H20A	0.9600
C8—C9	1.540 (4)	C20—H20B	0.9600
C8—H8A	0.9800	C20—H20C	0.9600
C18—O2—H1O2	109.5	C5—C10—H10A	105.5
C16—O4—H1O4	109.5	C12—C11—C9	113.5 (2)
C2—C1—C10	116.4 (3)	C12—C11—H11A	108.9
C2—C1—H1A	108.2	C9—C11—H11A	108.9
C10—C1—H1A	108.2	C12—C11—H11B	108.9
C2—C1—H1B	108.2	C9—C11—H11B	108.9
C10—C1—H1B	108.2	H11A—C11—H11B	107.7
H1A—C1—H1B	107.3	C13—C12—C11	113.7 (3)
C3—C2—C1	117.4 (3)	C13—C12—H12A	108.8
C3—C2—H2A	107.9	C11—C12—H12A	108.8
C1—C2—H2A	107.9	C13—C12—H12B	108.8
C3—C2—H2B	107.9	C11—C12—H12B	108.8
C1—C2—H2B	107.9	H12A—C12—H12B	107.7
H2A—C2—H2B	107.2	C17—C13—C15	111.0 (2)
O1—C3—C4	121.1 (3)	C17—C13—C12	110.1 (3)
O1—C3—C2	119.2 (3)	C15—C13—C12	109.7 (2)
C4—C3—C2	119.7 (3)	C17—C13—C14	111.2 (3)
C18—C4—C3	117.0 (3)	C15—C13—C14	104.7 (2)
C18—C4—C5	123.4 (3)	C12—C13—C14	110.2 (2)
C3—C4—C5	119.6 (3)	C8—C14—C13	112.6 (2)
C4—C5—C6	112.6 (2)	C8—C14—H14A	109.1
C4—C5—C19	108.5 (2)	C13—C14—H14A	109.1
C6—C5—C19	107.4 (2)	C8—C14—H14B	109.1
C4—C5—C10	109.8 (2)	C13—C14—H14B	109.1
C6—C5—C10	109.0 (2)	H14A—C14—H14B	107.8
C19—C5—C10	109.4 (2)	O3—C15—C16	118.9 (3)
C7—C6—C5	113.8 (2)	O3—C15—C13	122.2 (3)
C7—C6—H6A	108.8	C16—C15—C13	118.8 (3)
C5—C6—H6A	108.8	O4—C16—C15	113.8 (3)
C7—C6—H6B	108.8	O4—C16—H16A	108.8
C5—C6—H6B	108.8	C15—C16—H16A	108.8
H6A—C6—H6B	107.7	O4—C16—H16B	108.8
C6—C7—C8	109.5 (3)	C15—C16—H16B	108.8
C6—C7—H7A	109.8	H16A—C16—H16B	107.7
C8—C7—H7A	109.8	C13—C17—H17A	109.5
C6—C7—H7B	109.8	C13—C17—H17B	109.5
C8—C7—H7B	109.8	H17A—C17—H17B	109.5
H7A—C7—H7B	108.2	C13—C17—H17C	109.5
C7—C8—C14	111.9 (2)	H17A—C17—H17C	109.5
C7—C8—C9	112.3 (2)	H17B—C17—H17C	109.5
C14—C8—C9	112.6 (2)	O2—C18—C4	123.4 (3)
C7—C8—H8A	106.5	O2—C18—H18A	118.3
C14—C8—H8A	106.5	C4—C18—H18A	118.3
C9—C8—H8A	106.5	C5—C19—H19A	109.5
C20—C9—C8	111.5 (2)	C5—C19—H19B	109.5
C20—C9—C11	107.9 (2)	H19A—C19—H19B	109.5
C8—C9—C11	106.8 (2)	C5—C19—H19C	109.5
C20—C9—C10	112.4 (2)	H19A—C19—H19C	109.5
C8—C9—C10	108.6 (2)	H19B—C19—H19C	109.5
C11—C9—C10	109.5 (2)	C9—C20—H20A	109.5
C1—C10—C9	114.5 (2)	C9—C20—H20B	109.5
C1—C10—C5	110.2 (2)	H20A—C20—H20B	109.5
C9—C10—C5	114.9 (2)	C9—C20—H20C	109.5
C1—C10—H10A	105.5	H20A—C20—H20C	109.5
C9—C10—H10A	105.5	H20B—C20—H20C	109.5
C10—C1—C2—C3	−0.2 (4)	C8—C9—C10—C5	−52.4 (3)
C1—C2—C3—O1	−157.0 (3)	C11—C9—C10—C5	−168.7 (3)
C1—C2—C3—C4	23.7 (4)	C4—C5—C10—C1	57.8 (3)
O1—C3—C4—C18	−4.4 (4)	C6—C5—C10—C1	−178.4 (2)
C2—C3—C4—C18	175.0 (3)	C19—C5—C10—C1	−61.2 (3)
O1—C3—C4—C5	177.0 (2)	C4—C5—C10—C9	−73.3 (3)
C2—C3—C4—C5	−3.6 (4)	C6—C5—C10—C9	50.6 (3)
C18—C4—C5—C6	22.3 (4)	C19—C5—C10—C9	167.7 (2)
C3—C4—C5—C6	−159.2 (2)	C20—C9—C11—C12	−64.2 (3)
C18—C4—C5—C19	−96.4 (3)	C8—C9—C11—C12	55.8 (3)
C3—C4—C5—C19	82.1 (3)	C10—C9—C11—C12	173.2 (3)
C18—C4—C5—C10	144.0 (3)	C9—C11—C12—C13	−53.6 (4)
C3—C4—C5—C10	−37.5 (3)	C11—C12—C13—C17	−74.3 (3)
C4—C5—C6—C7	69.2 (3)	C11—C12—C13—C15	163.3 (3)
C19—C5—C6—C7	−171.3 (3)	C11—C12—C13—C14	48.6 (3)
C10—C5—C6—C7	−52.9 (3)	C7—C8—C14—C13	−174.0 (2)
C5—C6—C7—C8	58.1 (3)	C9—C8—C14—C13	58.3 (3)
C6—C7—C8—C14	172.7 (2)	C17—C13—C14—C8	71.3 (3)
C6—C7—C8—C9	−59.5 (3)	C15—C13—C14—C8	−168.8 (2)
C7—C8—C9—C20	−68.1 (3)	C12—C13—C14—C8	−51.0 (3)
C14—C8—C9—C20	59.3 (3)	C17—C13—C15—O3	−151.8 (4)
C7—C8—C9—C11	174.2 (2)	C12—C13—C15—O3	−30.0 (4)
C14—C8—C9—C11	−58.4 (3)	C14—C13—C15—O3	88.2 (4)
C7—C8—C9—C10	56.2 (3)	C17—C13—C15—C16	31.0 (4)
C14—C8—C9—C10	−176.4 (2)	C12—C13—C15—C16	152.8 (3)
C2—C1—C10—C9	91.3 (3)	C14—C13—C15—C16	−89.0 (3)
C2—C1—C10—C5	−40.0 (3)	O3—C15—C16—O4	−11.1 (5)
C20—C9—C10—C1	−57.5 (3)	C13—C15—C16—O4	166.3 (3)
C8—C9—C10—C1	178.7 (2)	C3—C4—C18—O2	4.4 (5)
C11—C9—C10—C1	62.4 (3)	C5—C4—C18—O2	−177.1 (3)
C20—C9—C10—C5	71.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.82	1.69	2.424 (4)	148
O4—H1O4···O1i	0.82	2.07	2.841 (3)	156
C1—H1B···O2ii	0.97	2.48	3.368 (5)	152
C12—H12A···O3	0.97	2.41	2.799 (4)	103
C17—H17A···O4iii	0.96	2.53	3.460 (5)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.82	1.69	2.424 (4)	148
O4—H1O4⋯O1i	0.82	2.07	2.841 (3)	156
C1—H1B⋯O2ii	0.97	2.48	3.368 (5)	152
C12—H12A⋯O3	0.97	2.41	2.799 (4)	103
C17—H17A⋯O4iii	0.96	2.53	3.460 (5)	164

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