4,4'-[(2R*,3R*,4R*,5R*)-3,4-Dimethyl-tetra-hydro-furan-2,5-di-yl]diphenol.

The title mol-ecule, C(18)H(20)O(3), is a furan-oid lignan extracted from the leaves of Larrea tridentata. The relative absolute configuration for the four chiral centers was established, showing that this compound is 4-epi-larreatricin, which has been previously reported in the literature. The mol-ecule displays noncrystallographic C(2) symmetry, with the methyl and phenol substituents alternating above and below the mean plane of the furan ring. The conformation of this ring is described by the pseudorotation phase angle P = 171.3° and the maximum out-of-plane pucker ν(m) = 37.7°. These parameters indicate that the furan ring adopts the same conformation as the ribose residues in B-DNA. The packing is dominated by inter-molecular O-H⋯O hydrogen bonds. The phenol hy-droxy groups form chains in the [110] direction and these chains inter-act via O-H⋯O(furan) contacts.

Related literature

For the extraction, synthesis, characterization and biological activity of the title compound, see: Konno et al. (1990 ▶); Moinuddin et al. (2003 ▶); Favela-Hernández et al. (2012 ▶). For the conformational analysis of sugar rings, see: Altona & Sundaralingam (1972 ▶); Sun et al. (2004 ▶). For an example of another naturally occurring furan­oid lignan, see: Soepadamo et al. (1991 ▶).

Experimental

Crystal data

C18H20O3

M = 284.34

Monoclinic,

a = 6.4225 (4) Å

b = 12.4973 (7) Å

c = 9.8176 (7) Å

β = 101.243 (6)°

V = 772.88 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.36 × 0.26 × 0.21 mm

Data collection

Agilent Xcalibur (Atlas, Gemini) diffractometer

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.980, T max = 0.985

5223 measured reflections

1592 independent reflections

1107 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.106

S = 1.05

1592 reflections

198 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: 1004 measured Friedel pairs merged for refinement

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039359/mw2082sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039359/mw2082Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039359/mw2082Isup3.cml

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

C18H20O3	F(000) = 304
Mr = 284.34	Dx = 1.222 Mg m−3
Monoclinic, P21	Melting point: 503 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 6.4225 (4) Å	Cell parameters from 1308 reflections
b = 12.4973 (7) Å	θ = 3.5–26.0°
c = 9.8176 (7) Å	µ = 0.08 mm−1
β = 101.243 (6)°	T = 298 K
V = 772.88 (9) Å3	Block, colourless
Z = 2	0.36 × 0.26 × 0.21 mm

Agilent Xcalibur (Atlas, Gemini) diffractometer	1592 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1107 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 10.4685 pixels mm-1	θmax = 26.1°, θmin = 3.5°
φ and ω scans	h = −7→6
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −15→15
Tmin = 0.980, Tmax = 0.985	l = −12→11
5223 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0498P)2] where P = (Fo2 + 2Fc2)/3
1592 reflections	(Δ/σ)max < 0.001
198 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.18 e Å−3
0 constraints	Absolute structure: 1004 measured Friedel pairs merged for refinement

	x	y	z	Uiso*/Ueq
O1	0.6576 (4)	0.17906 (19)	0.2077 (2)	0.0608 (7)
O2	0.3301 (4)	−0.29301 (19)	0.0656 (2)	0.0569 (6)
H2	0.377 (5)	−0.303 (4)	−0.014 (4)	0.085*
O3	0.9213 (4)	0.64265 (18)	0.0690 (3)	0.0741 (8)
H3	1.056 (8)	0.659 (4)	0.058 (5)	0.111*
C2	0.5625 (5)	0.1142 (3)	0.3000 (3)	0.0489 (8)
H2A	0.4333	0.1500	0.3155	0.059*
C3	0.7244 (5)	0.1130 (3)	0.4373 (4)	0.0588 (9)
H3A	0.8255	0.0553	0.4313	0.071*
C4	0.8399 (5)	0.2166 (3)	0.4337 (3)	0.0598 (9)
H4A	0.7472	0.2739	0.4551	0.072*
C5	0.8532 (5)	0.2269 (3)	0.2820 (4)	0.0519 (9)
H5A	0.9727	0.1835	0.2651	0.062*
C6	0.6305 (7)	0.0920 (5)	0.5619 (4)	0.0953 (16)
H6A	0.7419	0.0872	0.6426	0.143*
H6B	0.5530	0.0259	0.5498	0.143*
H6C	0.5362	0.1493	0.5737	0.143*
C7	1.0528 (6)	0.2277 (4)	0.5332 (4)	0.0903 (14)
H7A	1.1126	0.2967	0.5212	0.135*
H7B	1.1476	0.1728	0.5140	0.135*
H7C	1.0323	0.2207	0.6270	0.135*
C8	0.5031 (5)	0.0063 (2)	0.2373 (4)	0.0459 (8)
C9	0.6388 (5)	−0.0506 (3)	0.1717 (4)	0.0564 (9)
H9A	0.7700	−0.0214	0.1659	0.068*
C10	0.5841 (5)	−0.1507 (3)	0.1138 (4)	0.0574 (9)
H10A	0.6780	−0.1878	0.0700	0.069*
C11	0.3913 (5)	−0.1941 (3)	0.1217 (3)	0.0448 (8)
C12	0.2553 (5)	−0.1400 (3)	0.1891 (4)	0.0561 (9)
H12A	0.1254	−0.1701	0.1963	0.067*
C13	0.3120 (5)	−0.0407 (3)	0.2462 (4)	0.0571 (9)
H13A	0.2189	−0.0047	0.2918	0.069*
C14	0.8752 (5)	0.3372 (3)	0.2270 (3)	0.0467 (8)
C15	0.7158 (5)	0.4127 (3)	0.2230 (4)	0.0586 (10)
H15A	0.5943	0.3948	0.2563	0.070*
C16	0.7343 (5)	0.5140 (3)	0.1703 (4)	0.0615 (10)
H16A	0.6250	0.5632	0.1675	0.074*
C17	0.9120 (5)	0.5420 (3)	0.1225 (4)	0.0526 (9)
C18	1.0742 (5)	0.4688 (3)	0.1258 (4)	0.0535 (9)
H18A	1.1962	0.4877	0.0937	0.064*
C19	1.0533 (5)	0.3675 (3)	0.1771 (4)	0.0516 (9)
H19A	1.1621	0.3182	0.1781	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0838 (15)	0.0455 (15)	0.0496 (14)	−0.0226 (12)	0.0047 (11)	0.0036 (11)
O2	0.0778 (15)	0.0387 (14)	0.0569 (15)	−0.0091 (12)	0.0199 (11)	−0.0006 (13)
O3	0.0794 (17)	0.0361 (15)	0.109 (2)	−0.0074 (13)	0.0236 (16)	0.0085 (14)
C2	0.0552 (18)	0.037 (2)	0.055 (2)	−0.0024 (15)	0.0118 (15)	0.0019 (16)
C3	0.070 (2)	0.051 (2)	0.055 (2)	−0.0058 (18)	0.0119 (17)	0.0035 (19)
C4	0.063 (2)	0.059 (2)	0.054 (2)	−0.0017 (18)	0.0007 (15)	0.006 (2)
C5	0.0527 (19)	0.039 (2)	0.063 (2)	−0.0002 (15)	0.0098 (15)	−0.0003 (18)
C6	0.107 (3)	0.109 (4)	0.069 (3)	−0.019 (3)	0.013 (2)	0.015 (3)
C7	0.086 (3)	0.097 (4)	0.077 (3)	−0.015 (3)	−0.009 (2)	0.002 (3)
C8	0.0547 (19)	0.0343 (19)	0.049 (2)	−0.0024 (14)	0.0109 (15)	0.0031 (15)
C9	0.0549 (19)	0.048 (2)	0.070 (3)	−0.0090 (16)	0.0216 (17)	−0.006 (2)
C10	0.058 (2)	0.053 (2)	0.067 (2)	0.0024 (17)	0.0249 (17)	−0.005 (2)
C11	0.0588 (19)	0.0306 (18)	0.0461 (19)	−0.0029 (15)	0.0128 (14)	0.0048 (15)
C12	0.0563 (19)	0.043 (2)	0.073 (3)	−0.0117 (17)	0.0253 (17)	−0.0023 (19)
C13	0.062 (2)	0.048 (2)	0.067 (3)	−0.0035 (17)	0.0257 (17)	−0.0069 (19)
C14	0.0513 (18)	0.038 (2)	0.050 (2)	−0.0052 (14)	0.0076 (14)	−0.0030 (16)
C15	0.054 (2)	0.043 (2)	0.081 (3)	−0.0055 (16)	0.0191 (18)	−0.0015 (19)
C16	0.057 (2)	0.040 (2)	0.088 (3)	−0.0006 (16)	0.0154 (18)	0.003 (2)
C17	0.060 (2)	0.0313 (19)	0.064 (2)	−0.0072 (16)	0.0073 (16)	−0.0056 (17)
C18	0.0538 (19)	0.045 (2)	0.064 (2)	−0.0055 (16)	0.0176 (16)	−0.0077 (18)
C19	0.0507 (18)	0.037 (2)	0.068 (2)	0.0000 (15)	0.0155 (16)	−0.0045 (17)

O1—C2	1.437 (4)	C7—H7C	0.9600
O1—C5	1.452 (3)	C8—C9	1.378 (5)
O2—C11	1.378 (4)	C8—C13	1.379 (4)
O2—H2	0.90 (4)	C9—C10	1.390 (5)
O3—C17	1.368 (4)	C9—H9A	0.9300
O3—H3	0.92 (5)	C10—C11	1.368 (4)
C2—C8	1.501 (4)	C10—H10A	0.9300
C2—C3	1.533 (5)	C11—C12	1.373 (5)
C2—H2A	0.9800	C12—C13	1.381 (5)
C3—C6	1.489 (5)	C12—H12A	0.9300
C3—C4	1.496 (5)	C13—H13A	0.9300
C3—H3A	0.9800	C14—C19	1.383 (5)
C4—C5	1.513 (5)	C14—C15	1.387 (4)
C4—C7	1.524 (4)	C15—C16	1.381 (5)
C4—H4A	0.9800	C15—H15A	0.9300
C5—C14	1.497 (5)	C16—C17	1.362 (5)
C5—H5A	0.9800	C16—H16A	0.9300
C6—H6A	0.9600	C17—C18	1.382 (5)
C6—H6B	0.9600	C18—C19	1.379 (5)
C6—H6C	0.9600	C18—H18A	0.9300
C7—H7A	0.9600	C19—H19A	0.9300
C7—H7B	0.9600
C2—O1—C5	110.3 (2)	H7B—C7—H7C	109.5
C11—O2—H2	111 (3)	C9—C8—C13	117.5 (3)
C17—O3—H3	112 (3)	C9—C8—C2	121.5 (3)
O1—C2—C8	110.7 (3)	C13—C8—C2	121.0 (3)
O1—C2—C3	105.1 (2)	C8—C9—C10	121.5 (3)
C8—C2—C3	115.2 (3)	C8—C9—H9A	119.2
O1—C2—H2A	108.5	C10—C9—H9A	119.2
C8—C2—H2A	108.5	C11—C10—C9	119.6 (3)
C3—C2—H2A	108.5	C11—C10—H10A	120.2
C6—C3—C4	117.0 (4)	C9—C10—H10A	120.2
C6—C3—C2	114.2 (3)	C10—C11—C12	120.0 (3)
C4—C3—C2	103.0 (3)	C10—C11—O2	121.6 (3)
C6—C3—H3A	107.4	C12—C11—O2	118.4 (3)
C4—C3—H3A	107.4	C11—C12—C13	119.7 (3)
C2—C3—H3A	107.4	C11—C12—H12A	120.1
C3—C4—C5	102.7 (3)	C13—C12—H12A	120.1
C3—C4—C7	116.8 (3)	C8—C13—C12	121.7 (3)
C5—C4—C7	114.0 (3)	C8—C13—H13A	119.2
C3—C4—H4A	107.6	C12—C13—H13A	119.2
C5—C4—H4A	107.6	C19—C14—C15	117.4 (3)
C7—C4—H4A	107.6	C19—C14—C5	121.5 (3)
O1—C5—C14	109.3 (2)	C15—C14—C5	121.1 (3)
O1—C5—C4	104.5 (2)	C16—C15—C14	121.1 (3)
C14—C5—C4	117.4 (3)	C16—C15—H15A	119.4
O1—C5—H5A	108.4	C14—C15—H15A	119.4
C14—C5—H5A	108.4	C17—C16—C15	120.3 (3)
C4—C5—H5A	108.4	C17—C16—H16A	119.9
C3—C6—H6A	109.5	C15—C16—H16A	119.9
C3—C6—H6B	109.5	C16—C17—O3	118.1 (3)
H6A—C6—H6B	109.5	C16—C17—C18	120.0 (3)
C3—C6—H6C	109.5	O3—C17—C18	121.9 (3)
H6A—C6—H6C	109.5	C19—C18—C17	119.3 (3)
H6B—C6—H6C	109.5	C19—C18—H18A	120.3
C4—C7—H7A	109.5	C17—C18—H18A	120.3
C4—C7—H7B	109.5	C18—C19—C14	121.8 (3)
H7A—C7—H7B	109.5	C18—C19—H19A	119.1
C4—C7—H7C	109.5	C14—C19—H19A	119.1
H7A—C7—H7C	109.5
C5—O1—C2—C8	−131.3 (3)	C8—C9—C10—C11	0.1 (5)
C5—O1—C2—C3	−6.2 (3)	C9—C10—C11—C12	−1.4 (5)
O1—C2—C3—C6	155.4 (4)	C9—C10—C11—O2	179.9 (3)
C8—C2—C3—C6	−82.5 (4)	C10—C11—C12—C13	1.4 (5)
O1—C2—C3—C4	27.4 (3)	O2—C11—C12—C13	−179.9 (3)
C8—C2—C3—C4	149.6 (3)	C9—C8—C13—C12	−1.4 (5)
C6—C3—C4—C5	−163.5 (3)	C2—C8—C13—C12	−179.9 (3)
C2—C3—C4—C5	−37.3 (3)	C11—C12—C13—C8	0.1 (5)
C6—C3—C4—C7	71.0 (5)	O1—C5—C14—C19	−124.5 (3)
C2—C3—C4—C7	−162.8 (3)	C4—C5—C14—C19	116.8 (3)
C2—O1—C5—C14	−143.7 (3)	O1—C5—C14—C15	54.8 (4)
C2—O1—C5—C4	−17.2 (3)	C4—C5—C14—C15	−63.9 (4)
C3—C4—C5—O1	34.0 (3)	C19—C14—C15—C16	0.3 (5)
C7—C4—C5—O1	161.3 (3)	C5—C14—C15—C16	−179.0 (3)
C3—C4—C5—C14	155.2 (3)	C14—C15—C16—C17	−0.7 (6)
C7—C4—C5—C14	−77.5 (4)	C15—C16—C17—O3	178.8 (3)
O1—C2—C8—C9	44.0 (4)	C15—C16—C17—C18	0.4 (6)
C3—C2—C8—C9	−75.1 (4)	C16—C17—C18—C19	0.3 (5)
O1—C2—C8—C13	−137.5 (3)	O3—C17—C18—C19	−178.0 (3)
C3—C2—C8—C13	103.4 (4)	C17—C18—C19—C14	−0.7 (5)
C13—C8—C9—C10	1.3 (5)	C15—C14—C19—C18	0.4 (5)
C2—C8—C9—C10	179.9 (3)	C5—C14—C19—C18	179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2i	0.92 (5)	1.84 (5)	2.752 (4)	169 (5)
O2—H2···O1ii	0.90 (4)	1.89 (4)	2.723 (3)	154 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2i	0.92 (5)	1.84 (5)	2.752 (4)	169 (5)
O2—H2⋯O1ii	0.90 (4)	1.89 (4)	2.723 (3)	154 (3)

Symmetry codes: (i) ; (ii) .