11,12-Dihy-droxy-10,6,8,11,13-icetexapentan-1-one.

THE TITLE COMPOUND [SYSTEMATIC NAME: 14,15-dihy-droxy-7,7-dimethyl-13-(propan-2-yl)tricyclo-[9.4.0.0(3,8)]penta-deca-1(11),3(8),9,12,14-pentaen-4-one], C(20)H(24)O(3), is a new icetexane diterpenoid which was isolated from the roots of Premna obtusifolia (Verbenaceae). The mol-ecule has three fused rings: a cyclo-hexenone, a central cyclo-heptene and a benzene ring. The cyclo-hexenone ring is in an envelope conformation, whereas the cyclo-heptene ring is in a twisted boat conformation. Intra-molecular O-H⋯O hydrogen bonds generate S(5) and S(8) ring motifs. In the crystal, mol-ecules are linked into dimers through O-H⋯O hydrogen bonds. These dimers are arranged in to sheets parallel to the ac plane. C-H⋯O and weak C-H⋯π inter-actions are also present.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶) and for ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to Verbenaceae plants and the bioactivity of icetexane, see: Bunluepuech & Tewtrakul (2009 ▶); Hymavathi et al. (2009 ▶); Simmons & Sarpong (2009 ▶). For related structures, see: Asik et al. (2010 ▶); Razak et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H24O3

M = 312.39

Monoclinic,

a = 25.1090 (9) Å

b = 9.4317 (3) Å

c = 14.9609 (4) Å

β = 108.683 (2)°

V = 3356.35 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.60 × 0.32 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.953, T max = 0.977

60861 measured reflections

7404 independent reflections

6198 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.125

S = 1.03

7404 reflections

304 parameters

All H-atom parameters refined

Δρmax = 0.48 e Å−3

Δρmin = −0.21 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/S1600536810053754/ng5091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053754/ng5091Isup2.hkl

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

C20H24O3	F(000) = 1344
Mr = 312.39	Dx = 1.236 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7404 reflections
a = 25.1090 (9) Å	θ = 2.3–35.0°
b = 9.4317 (3) Å	µ = 0.08 mm−1
c = 14.9609 (4) Å	T = 100 K
β = 108.683 (2)°	Needle, yellow
V = 3356.35 (19) Å3	0.60 × 0.32 × 0.28 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	7404 independent reflections
Radiation source: sealed tube	6198 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 35.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −38→40
Tmin = 0.953, Tmax = 0.977	k = −14→15
60861 measured reflections	l = −24→24

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0755P)2 + 1.0087P] where P = (Fo2 + 2Fc2)/3
7404 reflections	(Δ/σ)max = 0.001
304 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.21 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	0.34135 (2)	0.18997 (7)	0.45441 (4)	0.02727 (13)
O2	0.22121 (2)	0.14713 (6)	0.42998 (3)	0.02042 (11)
H1O2	0.2573 (7)	0.1602 (17)	0.4448 (11)	0.048 (4)*
O3	0.11523 (2)	0.24175 (6)	0.35038 (3)	0.01917 (10)
H1O3	0.1377 (6)	0.2421 (15)	0.4088 (10)	0.041 (4)*
C1	0.35660 (3)	0.18067 (8)	0.38355 (5)	0.02009 (13)
C2	0.40308 (3)	0.27126 (10)	0.37203 (6)	0.02604 (15)
H2A	0.4322 (6)	0.2867 (15)	0.4357 (10)	0.038 (3)*
H2B	0.3867 (6)	0.3655 (16)	0.3534 (10)	0.040 (3)*
C3	0.42779 (3)	0.20818 (9)	0.30042 (6)	0.02461 (14)
H3A	0.4475 (5)	0.1170 (14)	0.3235 (9)	0.031 (3)*
H3B	0.4575 (6)	0.2728 (14)	0.2903 (9)	0.035 (3)*
C4	0.38338 (3)	0.17810 (8)	0.20403 (5)	0.01959 (12)
C5	0.33387 (3)	0.09795 (7)	0.21853 (5)	0.01718 (11)
C6	0.29158 (3)	0.04077 (8)	0.13478 (5)	0.02060 (13)
H6A	0.3058 (5)	0.0138 (14)	0.0831 (9)	0.030 (3)*
C7	0.23475 (3)	0.03856 (8)	0.11708 (5)	0.02164 (13)
H7A	0.2123 (5)	0.0114 (13)	0.0533 (8)	0.027 (3)*
C8	0.20317 (3)	0.08458 (7)	0.17837 (4)	0.01703 (11)
C9	0.22671 (3)	0.07722 (7)	0.27714 (4)	0.01548 (11)
C10	0.32690 (3)	0.08736 (7)	0.30526 (4)	0.01682 (11)
C11	0.19897 (3)	0.14125 (7)	0.33345 (4)	0.01495 (11)
C12	0.14429 (3)	0.19365 (7)	0.29375 (4)	0.01505 (11)
C13	0.11813 (3)	0.19232 (7)	0.19542 (4)	0.01734 (11)
C14	0.14864 (3)	0.14018 (8)	0.13931 (5)	0.01940 (12)
H14A	0.1327 (5)	0.1435 (13)	0.0691 (8)	0.029 (3)*
C15	0.05752 (3)	0.24151 (8)	0.15458 (5)	0.02181 (13)
H15A	0.0487 (6)	0.3020 (16)	0.2035 (10)	0.043 (4)*
C16	0.01786 (3)	0.11352 (11)	0.13660 (7)	0.03109 (18)
H16A	0.0246 (6)	0.0563 (16)	0.0858 (10)	0.041 (3)*
H16B	−0.0208 (6)	0.1452 (14)	0.1209 (10)	0.038 (3)*
H16C	0.0246 (6)	0.0539 (16)	0.1939 (10)	0.043 (4)*
C17	0.04657 (4)	0.32889 (10)	0.06447 (7)	0.03084 (17)
H17A	0.0749 (7)	0.4078 (17)	0.0732 (11)	0.051 (4)*
H17B	0.0075 (6)	0.3743 (15)	0.0475 (10)	0.040 (3)*
H17C	0.0477 (6)	0.2691 (16)	0.0078 (10)	0.043 (4)*
C18	0.41211 (4)	0.08869 (9)	0.14665 (6)	0.02682 (15)
H18A	0.3865 (6)	0.0729 (15)	0.0807 (10)	0.036 (3)*
H18B	0.4239 (6)	−0.0029 (16)	0.1787 (9)	0.039 (3)*
H18C	0.4464 (5)	0.1393 (14)	0.1442 (9)	0.034 (3)*
C19	0.36195 (4)	0.31667 (9)	0.15095 (7)	0.03147 (17)
H19A	0.3940 (6)	0.3712 (17)	0.1398 (11)	0.048 (4)*
H19B	0.3440 (6)	0.3764 (17)	0.1896 (10)	0.045 (4)*
H19C	0.3354 (6)	0.2977 (15)	0.0893 (10)	0.037 (3)*
C20	0.28082 (3)	−0.00267 (7)	0.31829 (5)	0.01867 (12)
H20A	0.2799 (5)	−0.0936 (12)	0.2844 (8)	0.022 (3)*
H20B	0.2880 (4)	−0.0209 (12)	0.3870 (8)	0.022 (2)*

	U11	U22	U33	U12	U13	U23
O1	0.0226 (2)	0.0428 (3)	0.0156 (2)	0.0040 (2)	0.00490 (18)	−0.0048 (2)
O2	0.0181 (2)	0.0313 (3)	0.01191 (19)	0.00406 (19)	0.00491 (16)	0.00394 (17)
O3	0.0166 (2)	0.0264 (2)	0.0148 (2)	0.00275 (17)	0.00536 (16)	−0.00128 (17)
C1	0.0154 (3)	0.0273 (3)	0.0159 (3)	0.0042 (2)	0.0026 (2)	−0.0018 (2)
C2	0.0178 (3)	0.0336 (4)	0.0254 (3)	−0.0039 (3)	0.0051 (2)	−0.0100 (3)
C3	0.0174 (3)	0.0287 (4)	0.0284 (3)	−0.0002 (2)	0.0082 (2)	−0.0037 (3)
C4	0.0206 (3)	0.0185 (3)	0.0220 (3)	0.0002 (2)	0.0100 (2)	−0.0002 (2)
C5	0.0178 (3)	0.0177 (3)	0.0167 (2)	0.0012 (2)	0.0065 (2)	−0.0009 (2)
C6	0.0210 (3)	0.0246 (3)	0.0174 (3)	0.0002 (2)	0.0078 (2)	−0.0051 (2)
C7	0.0210 (3)	0.0267 (3)	0.0172 (3)	0.0002 (2)	0.0061 (2)	−0.0069 (2)
C8	0.0169 (2)	0.0185 (3)	0.0154 (2)	−0.0007 (2)	0.0048 (2)	−0.0037 (2)
C9	0.0155 (2)	0.0155 (2)	0.0158 (2)	0.00006 (19)	0.00547 (19)	0.00067 (19)
C10	0.0154 (2)	0.0197 (3)	0.0151 (2)	0.0027 (2)	0.00442 (19)	0.0006 (2)
C11	0.0157 (2)	0.0166 (2)	0.0127 (2)	0.00038 (19)	0.00469 (18)	0.00190 (19)
C12	0.0152 (2)	0.0160 (2)	0.0140 (2)	−0.00001 (19)	0.00473 (19)	−0.00030 (18)
C13	0.0156 (2)	0.0200 (3)	0.0147 (2)	0.0005 (2)	0.00235 (19)	−0.0028 (2)
C14	0.0182 (3)	0.0241 (3)	0.0143 (2)	−0.0001 (2)	0.0030 (2)	−0.0046 (2)
C15	0.0183 (3)	0.0285 (3)	0.0157 (3)	0.0051 (2)	0.0013 (2)	−0.0036 (2)
C16	0.0164 (3)	0.0421 (5)	0.0334 (4)	−0.0012 (3)	0.0060 (3)	0.0097 (3)
C17	0.0259 (4)	0.0298 (4)	0.0305 (4)	0.0017 (3)	0.0002 (3)	0.0083 (3)
C18	0.0278 (3)	0.0259 (3)	0.0338 (4)	−0.0016 (3)	0.0198 (3)	−0.0033 (3)
C19	0.0345 (4)	0.0222 (3)	0.0384 (4)	0.0030 (3)	0.0126 (4)	0.0088 (3)
C20	0.0184 (3)	0.0186 (3)	0.0201 (3)	0.0032 (2)	0.0077 (2)	0.0038 (2)

O1—C1	1.2403 (9)	C9—C20	1.5022 (9)
O2—C11	1.3725 (8)	C10—C20	1.4976 (9)
O2—H1O2	0.869 (16)	C11—C12	1.3998 (9)
O3—C12	1.3610 (8)	C12—C13	1.4058 (9)
O3—H1O3	0.875 (14)	C13—C14	1.3948 (9)
C1—C10	1.4638 (10)	C13—C15	1.5196 (9)
C1—C2	1.5003 (11)	C14—H14A	0.997 (12)
C2—C3	1.5208 (11)	C15—C17	1.5280 (12)
C2—H2A	1.008 (14)	C15—C16	1.5329 (12)
C2—H2B	0.982 (15)	C15—H15A	1.006 (15)
C3—C4	1.5406 (11)	C16—H16A	0.989 (14)
C3—H3A	0.996 (13)	C16—H16B	0.969 (14)
C3—H3B	1.011 (13)	C16—H16C	0.993 (15)
C4—C5	1.5286 (10)	C17—H17A	1.008 (16)
C4—C19	1.5345 (11)	C17—H17B	1.026 (14)
C4—C18	1.5379 (10)	C17—H17C	1.026 (15)
C5—C10	1.3674 (9)	C18—H18A	1.001 (13)
C5—C6	1.4615 (10)	C18—H18B	0.987 (15)
C6—C7	1.3655 (10)	C18—H18C	0.996 (13)
C6—H6A	0.984 (12)	C19—H19A	1.013 (15)
C7—C8	1.4574 (9)	C19—H19B	1.011 (15)
C7—H7A	0.975 (12)	C19—H19C	0.966 (14)
C8—C9	1.4065 (9)	C20—H20A	0.993 (11)
C8—C14	1.4068 (9)	C20—H20B	1.000 (11)
C9—C11	1.3912 (9)
C11—O2—H1O2	108.3 (10)	O3—C12—C13	119.36 (6)
C12—O3—H1O3	108.7 (9)	C11—C12—C13	120.46 (6)
O1—C1—C10	120.59 (7)	C14—C13—C12	118.06 (6)
O1—C1—C2	121.49 (7)	C14—C13—C15	122.54 (6)
C10—C1—C2	117.78 (6)	C12—C13—C15	119.35 (6)
C1—C2—C3	111.47 (6)	C13—C14—C8	122.04 (6)
C1—C2—H2A	109.2 (8)	C13—C14—H14A	120.7 (7)
C3—C2—H2A	112.7 (8)	C8—C14—H14A	117.3 (7)
C1—C2—H2B	106.1 (8)	C13—C15—C17	113.17 (6)
C3—C2—H2B	112.5 (8)	C13—C15—C16	109.93 (6)
H2A—C2—H2B	104.4 (11)	C17—C15—C16	110.29 (6)
C2—C3—C4	113.28 (6)	C13—C15—H15A	107.8 (8)
C2—C3—H3A	111.3 (7)	C17—C15—H15A	108.4 (9)
C4—C3—H3A	107.2 (7)	C16—C15—H15A	107.0 (9)
C2—C3—H3B	110.9 (7)	C15—C16—H16A	107.6 (8)
C4—C3—H3B	108.5 (7)	C15—C16—H16B	110.0 (8)
H3A—C3—H3B	105.3 (10)	H16A—C16—H16B	112.7 (11)
C5—C4—C19	109.16 (6)	C15—C16—H16C	111.9 (8)
C5—C4—C18	110.87 (6)	H16A—C16—H16C	109.3 (12)
C19—C4—C18	109.12 (7)	H16B—C16—H16C	105.3 (11)
C5—C4—C3	109.63 (6)	C15—C17—H17A	111.3 (9)
C19—C4—C3	110.87 (7)	C15—C17—H17B	109.3 (8)
C18—C4—C3	107.17 (6)	H17A—C17—H17B	107.7 (12)
C10—C5—C6	120.53 (6)	C15—C17—H17C	112.8 (8)
C10—C5—C4	121.86 (6)	H17A—C17—H17C	108.0 (12)
C6—C5—C4	117.47 (6)	H17B—C17—H17C	107.6 (11)
C7—C6—C5	126.80 (6)	C4—C18—H18A	111.3 (8)
C7—C6—H6A	117.7 (7)	C4—C18—H18B	109.3 (8)
C5—C6—H6A	114.9 (7)	H18A—C18—H18B	110.3 (11)
C6—C7—C8	128.23 (6)	C4—C18—H18C	108.9 (8)
C6—C7—H7A	115.8 (7)	H18A—C18—H18C	109.0 (10)
C8—C7—H7A	115.7 (7)	H18B—C18—H18C	108.0 (11)
C9—C8—C14	118.71 (6)	C4—C19—H19A	110.6 (9)
C9—C8—C7	121.08 (6)	C4—C19—H19B	109.0 (9)
C14—C8—C7	120.20 (6)	H19A—C19—H19B	109.6 (12)
C11—C9—C8	119.44 (6)	C4—C19—H19C	110.9 (8)
C11—C9—C20	122.14 (6)	H19A—C19—H19C	106.1 (12)
C8—C9—C20	118.41 (6)	H19B—C19—H19C	110.6 (12)
C5—C10—C1	121.89 (6)	C10—C20—C9	107.30 (5)
C5—C10—C20	120.26 (6)	C10—C20—H20A	108.4 (6)
C1—C10—C20	116.97 (6)	C9—C20—H20A	110.8 (6)
O2—C11—C9	122.74 (6)	C10—C20—H20B	109.8 (6)
O2—C11—C12	116.45 (5)	C9—C20—H20B	110.4 (6)
C9—C11—C12	120.63 (6)	H20A—C20—H20B	110.1 (9)
O3—C12—C11	120.14 (5)
O1—C1—C2—C3	160.07 (7)	O1—C1—C10—C20	−4.42 (10)
C10—C1—C2—C3	−24.13 (10)	C2—C1—C10—C20	179.74 (6)
C1—C2—C3—C4	54.32 (9)	C8—C9—C11—O2	−175.30 (6)
C2—C3—C4—C5	−48.51 (9)	C20—C9—C11—O2	5.92 (10)
C2—C3—C4—C19	72.08 (9)	C8—C9—C11—C12	9.76 (9)
C2—C3—C4—C18	−168.92 (7)	C20—C9—C11—C12	−169.02 (6)
C19—C4—C5—C10	−108.14 (8)	O2—C11—C12—O3	−2.53 (9)
C18—C4—C5—C10	131.62 (7)	C9—C11—C12—O3	172.71 (6)
C3—C4—C5—C10	13.49 (9)	O2—C11—C12—C13	179.82 (6)
C19—C4—C5—C6	67.64 (8)	C9—C11—C12—C13	−4.93 (10)
C18—C4—C5—C6	−52.61 (8)	O3—C12—C13—C14	−178.92 (6)
C3—C4—C5—C6	−170.74 (6)	C11—C12—C13—C14	−1.26 (10)
C10—C5—C6—C7	35.04 (12)	O3—C12—C13—C15	−1.36 (10)
C4—C5—C6—C7	−140.79 (8)	C11—C12—C13—C15	176.30 (6)
C5—C6—C7—C8	−3.68 (14)	C12—C13—C14—C8	2.58 (11)
C6—C7—C8—C9	−29.82 (12)	C15—C13—C14—C8	−174.89 (7)
C6—C7—C8—C14	148.89 (8)	C9—C8—C14—C13	2.18 (10)
C14—C8—C9—C11	−8.32 (10)	C7—C8—C14—C13	−176.55 (7)
C7—C8—C9—C11	170.41 (6)	C14—C13—C15—C17	−42.19 (10)
C14—C8—C9—C20	170.51 (6)	C12—C13—C15—C17	140.37 (7)
C7—C8—C9—C20	−10.77 (9)	C14—C13—C15—C16	81.62 (9)
C6—C5—C10—C1	−159.14 (6)	C12—C13—C15—C16	−95.82 (8)
C4—C5—C10—C1	16.50 (10)	C5—C10—C20—C9	−75.85 (8)
C6—C5—C10—C20	9.77 (10)	C1—C10—C20—C9	93.60 (7)
C4—C5—C10—C20	−174.58 (6)	C11—C9—C20—C10	−106.68 (7)
O1—C1—C10—C5	164.85 (7)	C8—C9—C20—C10	74.52 (7)
C2—C1—C10—C5	−10.99 (10)

Cg1 is the centroid of C8–C9/C11–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.870 (18)	2.088 (18)	2.9479 (8)	169.8 (15)
O2—H1O2···O2i	0.870 (18)	2.541 (16)	2.8818 (7)	104.3 (12)
O3—H1O3···O2	0.875 (14)	2.208 (16)	2.6955 (7)	114.9 (12)
O3—H1O3···O1i	0.875 (14)	2.046 (14)	2.8448 (7)	151.3 (14)
C7—H7A···O2ii	0.974 (12)	2.440 (12)	3.2262 (9)	137.5 (10)
C15—H15A···O3	1.007 (15)	2.364 (15)	2.8216 (8)	106.6 (10)
C18—H18B···O3iii	0.986 (15)	2.585 (15)	3.3467 (10)	134.1 (11)
C19—H19B···Cg1ii	1.011 (15)	2.798 (16)	3.7130 (10)	150.8 (12)
C20—H20A···Cg1iv	0.993 (11)	2.847 (12)	3.7506 (8)	151.6 (9)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C8–C9/C11–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.870 (18)	2.088 (18)	2.9479 (8)	169.8 (15)
O2—H1O2⋯O2i	0.870 (18)	2.541 (16)	2.8818 (7)	104.3 (12)
O3—H1O3⋯O2	0.875 (14)	2.208 (16)	2.6955 (7)	114.9 (12)
O3—H1O3⋯O1i	0.875 (14)	2.046 (14)	2.8448 (7)	151.3 (14)
C7—H7A⋯O2ii	0.974 (12)	2.440 (12)	3.2262 (9)	137.5 (10)
C15—H15A⋯O3	1.007 (15)	2.364 (15)	2.8216 (8)	106.6 (10)
C18—H18B⋯O3iii	0.986 (15)	2.585 (15)	3.3467 (10)	134.1 (11)
C19—H19B⋯Cg1ii	1.011 (15)	2.798 (16)	3.7130 (10)	150.8 (12)
C20—H20A⋯Cg1iv	0.993 (11)	2.847 (12)	3.7506 (8)	151.6 (9)

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