2,2'-Dimethoxy-4,4'-[rel-(2R,3S)-2,3-di-methylbutane-1,4-diyl]diphenol.

The title mol-ecule, C(20)H(26)O(4), commonly known as meso-dihydro-guaiaretic acid, is a naturally occurring lignan extracted from Larrea tridentata and other plants. The mol-ecule has a noncrystallographic inversion center situated at the midpoint of the central C-C bond, generating the meso stereoisomer. The central C-C-C-C alkyl chain displays an all-trans conformation, allowing an almost parallel arrangement of the benzene rings, which make a dihedral angle of 5.0 (3)°. Both hydr-oxy groups form weak O-H⋯O-H chains of hydrogen bonds along [100]. The resulting supra-molecular structure is an undulating plane parallel to (010).

Related literature

For the extraction of the title mol­ecule from Larrea tridentata, see: Waller & Gisvold (1945 ▶). For previous phytochemical characterizations, see: Gnabre et al. (1995 ▶); Konno et al. (1990 ▶); Tyler & Foster (1999 ▶). For the activity of this plant against Mycobacterium tuberculosis, see: Camacho-Corona et al. (2008 ▶).

Experimental

Crystal data

C20H26O4

M = 330.41

Orthorhombic,

a = 5.1355 (8) Å

b = 12.024 (2) Å

c = 30.158 (5) Å

V = 1862.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.50 × 0.40 × 0.18 mm

Data collection

Siemens P4 diffractometer

Absorption correction: none

3966 measured reflections

1937 independent reflections

1196 reflections with I > 2σ(I)

R int = 0.159

2 standard reflections every 98 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.139

S = 1.00

1937 reflections

227 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; 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., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017292/is2391sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017292/is2391Isup2.hkl

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

C20H26O4	Dx = 1.179 Mg m−3
Mr = 330.41	Melting point: 360 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 54 reflections
a = 5.1355 (8) Å	θ = 4.4–11.0°
b = 12.024 (2) Å	µ = 0.08 mm−1
c = 30.158 (5) Å	T = 298 K
V = 1862.2 (5) Å3	Plate, colourless
Z = 4	0.50 × 0.40 × 0.18 mm
F(000) = 712

Siemens P4 diffractometer	Rint = 0.159
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.8°
graphite	h = −6→6
ω scans	k = −14→1
3966 measured reflections	l = −35→1
1937 independent reflections	2 standard reflections every 98 reflections
1196 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3
1937 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.18 e Å−3
2 restraints	Δρmin = −0.17 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
O1	0.7382 (7)	0.4677 (2)	0.26965 (7)	0.0629 (8)
O2	0.4317 (8)	0.3034 (3)	0.24222 (9)	0.0732 (10)
H2	0.580 (6)	0.327 (5)	0.2350 (16)	0.110*
O13	0.2881 (7)	0.5103 (3)	0.67472 (8)	0.0703 (9)
O14	0.5820 (8)	0.6849 (3)	0.69302 (8)	0.0712 (10)
H14	0.451 (8)	0.650 (4)	0.7037 (14)	0.107*
C1	0.5599 (9)	0.4296 (3)	0.29987 (11)	0.0493 (11)
C2	0.4047 (9)	0.3442 (3)	0.28494 (10)	0.0505 (11)
C3	0.2159 (10)	0.2992 (3)	0.31135 (13)	0.0614 (12)
H3A	0.1110	0.2419	0.3009	0.074*
C4	0.1827 (10)	0.3406 (4)	0.35425 (11)	0.0619 (12)
H4A	0.0536	0.3109	0.3723	0.074*
C5	0.3379 (9)	0.4242 (4)	0.36995 (11)	0.0540 (11)
C6	0.5250 (10)	0.4695 (3)	0.34251 (11)	0.0541 (11)
H6A	0.6286	0.5275	0.3528	0.065*
C7	0.3030 (9)	0.4706 (4)	0.41668 (11)	0.0676 (13)
H7A	0.1446	0.4400	0.4292	0.081*
H7B	0.2811	0.5506	0.4147	0.081*
C8	0.5292 (10)	0.4456 (3)	0.44808 (11)	0.0516 (11)
H8B	0.6859	0.4789	0.4352	0.062*
C9	0.4850 (9)	0.5012 (3)	0.49355 (10)	0.0494 (10)
H9A	0.3223	0.4712	0.5056	0.059*
C10	0.7010 (10)	0.4725 (3)	0.52650 (10)	0.0656 (14)
H10B	0.7041	0.3925	0.5306	0.079*
H10C	0.8668	0.4941	0.5137	0.079*
C11	0.6747 (9)	0.5273 (3)	0.57162 (11)	0.0556 (12)
C12	0.4889 (9)	0.4893 (3)	0.60132 (11)	0.0549 (11)
H12C	0.3845	0.4288	0.5941	0.066*
C13	0.4594 (10)	0.5421 (3)	0.64204 (11)	0.0518 (11)
C14	0.6091 (10)	0.6318 (3)	0.65279 (11)	0.0532 (11)
C15	0.7953 (11)	0.6697 (3)	0.62395 (12)	0.0658 (12)
H15B	0.8990	0.7304	0.6313	0.079*
C16	0.8261 (11)	0.6157 (4)	0.58344 (12)	0.0634 (13)
H16A	0.9535	0.6406	0.5639	0.076*
C17	0.9001 (11)	0.5584 (4)	0.28192 (12)	0.0683 (13)
H17B	1.0187	0.5746	0.2582	0.102*
H17C	0.9968	0.5393	0.3081	0.102*
H17D	0.7943	0.6225	0.2878	0.102*
C18	0.5765 (13)	0.3217 (3)	0.45129 (11)	0.0801 (16)
H18C	0.5897	0.2908	0.4220	0.120*
H18D	0.4342	0.2873	0.4667	0.120*
H18E	0.7355	0.3083	0.4672	0.120*
C19	0.4509 (15)	0.6260 (3)	0.48960 (12)	0.0877 (18)
H19D	0.4239	0.6573	0.5185	0.131*
H19E	0.3030	0.6419	0.4712	0.131*
H19F	0.6043	0.6580	0.4766	0.131*
C20	0.1181 (10)	0.4196 (4)	0.66747 (13)	0.0668 (13)
H20B	0.0149	0.4072	0.6936	0.100*
H20C	0.2181	0.3541	0.6611	0.100*
H20D	0.0058	0.4358	0.6429	0.100*

	U11	U22	U33	U12	U13	U23
O1	0.069 (2)	0.0660 (18)	0.0537 (14)	−0.0157 (19)	0.0004 (17)	−0.0018 (13)
O2	0.084 (3)	0.086 (2)	0.0494 (16)	−0.026 (2)	−0.0004 (17)	−0.0086 (14)
O13	0.078 (2)	0.082 (2)	0.0511 (14)	−0.022 (2)	0.0105 (16)	−0.0045 (14)
O14	0.090 (3)	0.070 (2)	0.0543 (16)	−0.020 (2)	0.0049 (18)	−0.0109 (14)
C1	0.049 (3)	0.054 (2)	0.045 (2)	−0.002 (2)	−0.008 (2)	0.0090 (18)
C2	0.055 (3)	0.053 (2)	0.044 (2)	0.001 (3)	−0.008 (2)	0.0010 (18)
C3	0.057 (3)	0.064 (3)	0.063 (2)	−0.011 (3)	−0.008 (2)	0.004 (2)
C4	0.049 (3)	0.080 (3)	0.056 (2)	−0.006 (3)	−0.007 (2)	0.008 (2)
C5	0.046 (3)	0.069 (3)	0.047 (2)	0.013 (3)	−0.005 (2)	−0.002 (2)
C6	0.049 (3)	0.061 (3)	0.052 (2)	0.002 (3)	−0.007 (2)	0.0010 (19)
C7	0.050 (3)	0.101 (3)	0.052 (2)	0.011 (3)	−0.004 (2)	−0.006 (2)
C8	0.047 (3)	0.063 (3)	0.0448 (19)	−0.004 (3)	0.008 (2)	0.0034 (18)
C9	0.045 (2)	0.058 (2)	0.0451 (19)	0.003 (3)	0.004 (2)	0.0060 (17)
C10	0.066 (3)	0.084 (3)	0.047 (2)	0.015 (3)	0.001 (2)	0.000 (2)
C11	0.055 (3)	0.067 (3)	0.045 (2)	0.010 (3)	−0.004 (2)	0.005 (2)
C12	0.059 (3)	0.055 (2)	0.051 (2)	0.001 (3)	−0.009 (2)	−0.0018 (19)
C13	0.052 (3)	0.059 (2)	0.044 (2)	0.002 (3)	−0.003 (2)	0.0064 (19)
C14	0.067 (3)	0.045 (2)	0.048 (2)	0.002 (3)	−0.002 (2)	0.0045 (19)
C15	0.075 (3)	0.063 (3)	0.060 (2)	−0.010 (3)	−0.001 (3)	0.009 (2)
C16	0.064 (3)	0.076 (3)	0.051 (2)	−0.007 (3)	0.006 (2)	0.013 (2)
C17	0.072 (4)	0.067 (3)	0.066 (2)	−0.016 (3)	−0.007 (3)	0.012 (2)
C18	0.116 (5)	0.066 (3)	0.058 (2)	0.016 (4)	0.002 (3)	−0.004 (2)
C19	0.122 (5)	0.068 (3)	0.073 (3)	0.025 (4)	−0.026 (3)	−0.005 (2)
C20	0.059 (3)	0.069 (3)	0.073 (3)	−0.014 (3)	−0.001 (3)	0.008 (2)

O1—C1	1.371 (5)	C9—H9A	0.9800
O1—C17	1.420 (5)	C10—C11	1.518 (5)
O2—C2	1.386 (5)	C10—H10B	0.9700
O2—H2	0.84 (2)	C10—H10C	0.9700
O13—C13	1.376 (5)	C11—C16	1.364 (6)
O13—C20	1.414 (5)	C11—C12	1.386 (6)
O14—C14	1.378 (5)	C12—C13	1.391 (5)
O14—H14	0.86 (2)	C12—H12C	0.9300
C1—C2	1.375 (6)	C13—C14	1.363 (6)
C1—C6	1.384 (5)	C14—C15	1.371 (6)
C2—C3	1.367 (6)	C15—C16	1.393 (5)
C3—C4	1.396 (5)	C15—H15B	0.9300
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.368 (6)	C17—H17B	0.9600
C4—H4A	0.9300	C17—H17C	0.9600
C5—C6	1.380 (6)	C17—H17D	0.9600
C5—C7	1.526 (5)	C18—H18C	0.9600
C6—H6A	0.9300	C18—H18D	0.9600
C7—C8	1.529 (6)	C18—H18E	0.9600
C7—H7A	0.9700	C19—H19D	0.9600
C7—H7B	0.9700	C19—H19E	0.9600
C8—C18	1.512 (6)	C19—H19F	0.9600
C8—C9	1.542 (5)	C20—H20B	0.9600
C8—H8B	0.9800	C20—H20C	0.9600
C9—C19	1.516 (5)	C20—H20D	0.9600
C9—C10	1.529 (6)
C1—O1—C17	118.3 (3)	C9—C10—H10C	108.6
C2—O2—H2	102 (4)	H10B—C10—H10C	107.5
C13—O13—C20	119.9 (3)	C16—C11—C12	118.7 (4)
C14—O14—H14	101 (3)	C16—C11—C10	121.4 (4)
O1—C1—C2	114.8 (3)	C12—C11—C10	119.8 (4)
O1—C1—C6	126.0 (4)	C11—C12—C13	119.6 (4)
C2—C1—C6	119.2 (4)	C11—C12—H12C	120.2
C3—C2—C1	121.1 (4)	C13—C12—H12C	120.2
C3—C2—O2	118.2 (4)	C14—C13—O13	114.2 (3)
C1—C2—O2	120.7 (4)	C14—C13—C12	120.7 (4)
C2—C3—C4	119.0 (4)	O13—C13—C12	125.1 (4)
C2—C3—H3A	120.5	C13—C14—C15	120.4 (4)
C4—C3—H3A	120.5	C13—C14—O14	121.3 (4)
C5—C4—C3	120.8 (4)	C15—C14—O14	118.3 (4)
C5—C4—H4A	119.6	C14—C15—C16	118.7 (4)
C3—C4—H4A	119.6	C14—C15—H15B	120.6
C4—C5—C6	119.2 (3)	C16—C15—H15B	120.6
C4—C5—C7	121.3 (4)	C11—C16—C15	121.8 (4)
C6—C5—C7	119.4 (4)	C11—C16—H16A	119.1
C5—C6—C1	120.7 (4)	C15—C16—H16A	119.1
C5—C6—H6A	119.7	O1—C17—H17B	109.5
C1—C6—H6A	119.7	O1—C17—H17C	109.5
C5—C7—C8	114.3 (4)	H17B—C17—H17C	109.5
C5—C7—H7A	108.7	O1—C17—H17D	109.5
C8—C7—H7A	108.7	H17B—C17—H17D	109.5
C5—C7—H7B	108.7	H17C—C17—H17D	109.5
C8—C7—H7B	108.7	C8—C18—H18C	109.5
H7A—C7—H7B	107.6	C8—C18—H18D	109.5
C18—C8—C7	110.8 (4)	H18C—C18—H18D	109.5
C18—C8—C9	113.2 (3)	C8—C18—H18E	109.5
C7—C8—C9	110.7 (4)	H18C—C18—H18E	109.5
C18—C8—H8B	107.3	H18D—C18—H18E	109.5
C7—C8—H8B	107.3	C9—C19—H19D	109.5
C9—C8—H8B	107.3	C9—C19—H19E	109.5
C19—C9—C10	111.0 (4)	H19D—C19—H19E	109.5
C19—C9—C8	112.1 (3)	C9—C19—H19F	109.5
C10—C9—C8	111.9 (3)	H19D—C19—H19F	109.5
C19—C9—H9A	107.2	H19E—C19—H19F	109.5
C10—C9—H9A	107.2	O13—C20—H20B	109.5
C8—C9—H9A	107.2	O13—C20—H20C	109.5
C11—C10—C9	114.9 (4)	H20B—C20—H20C	109.5
C11—C10—H10B	108.6	O13—C20—H20D	109.5
C9—C10—H10B	108.6	H20B—C20—H20D	109.5
C11—C10—H10C	108.6	H20C—C20—H20D	109.5
C17—O1—C1—C2	177.9 (4)	C18—C8—C9—C10	51.8 (6)
C17—O1—C1—C6	−1.7 (6)	C7—C8—C9—C10	176.9 (3)
O1—C1—C2—C3	−179.1 (4)	C19—C9—C10—C11	52.1 (5)
C6—C1—C2—C3	0.6 (6)	C8—C9—C10—C11	178.2 (4)
O1—C1—C2—O2	−0.6 (6)	C9—C10—C11—C16	−104.1 (5)
C6—C1—C2—O2	179.0 (4)	C9—C10—C11—C12	74.2 (5)
C1—C2—C3—C4	−0.5 (6)	C16—C11—C12—C13	0.5 (6)
O2—C2—C3—C4	−178.9 (4)	C10—C11—C12—C13	−177.8 (4)
C2—C3—C4—C5	−0.6 (6)	C20—O13—C13—C14	178.9 (4)
C3—C4—C5—C6	1.5 (6)	C20—O13—C13—C12	−2.3 (6)
C3—C4—C5—C7	179.7 (4)	C11—C12—C13—C14	0.8 (6)
C4—C5—C6—C1	−1.4 (6)	C11—C12—C13—O13	−177.9 (4)
C7—C5—C6—C1	−179.6 (4)	O13—C13—C14—C15	177.5 (4)
O1—C1—C6—C5	179.9 (4)	C12—C13—C14—C15	−1.5 (6)
C2—C1—C6—C5	0.3 (6)	O13—C13—C14—O14	−1.1 (6)
C4—C5—C7—C8	112.6 (5)	C12—C13—C14—O14	−180.0 (4)
C6—C5—C7—C8	−69.3 (5)	C13—C14—C15—C16	0.7 (7)
C5—C7—C8—C18	−56.9 (5)	O14—C14—C15—C16	179.2 (4)
C5—C7—C8—C9	176.7 (3)	C12—C11—C16—C15	−1.3 (6)
C18—C8—C9—C19	177.3 (5)	C10—C11—C16—C15	177.0 (4)
C7—C8—C9—C19	−57.6 (6)	C14—C15—C16—C11	0.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O14i	0.84 (2)	2.15 (3)	2.908 (6)	149 (5)
O14—H14···O2ii	0.86 (2)	2.35 (4)	3.030 (5)	137 (5)
O2—H2···O1	0.84 (2)	2.14 (5)	2.658 (4)	119 (5)
O14—H14···O13	0.86 (2)	2.07 (4)	2.644 (5)	124 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O14i	0.84 (2)	2.15 (3)	2.908 (6)	149 (5)
O14—H14⋯O2ii	0.86 (2)	2.35 (4)	3.030 (5)	137 (5)

Symmetry codes: (i) ; (ii) .