erythro-2-(2,6-Di­methoxy­phenoxy)-1-(3,4,5-tri­methoxy­phenyl)-1,3-propane­diol

In the crystals of the title lignin model compound, C₂₀H₂₆O₈, the mol­ecules adopt a conformation in which the bulky 2,6-di­methoxy­phenoxy and 3,4,5-tri­methoxy­phenyl groups are distant from each other. The O(phenoxy)-C-C-C(phenyl) torsion angle between these groups is 178.58 (7)°. The hydrogen-bonding pattern is discussed in terms of graph-set theory.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.124
• Data-to-parameter ratio = 25.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C20H26O8	Dx = 1.268 Mg m^−3
Mr = 394.41	Melting point: 105°C K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.7627 (2) Å	Cell parameters from 8192 reflections
b = 9.6220 (2) Å	θ = 1.8–32.9°
c = 18.7387 (3) Å	µ = 0.10 mm^−1
β = 103.034 (1)°	T = 183 K
V = 2066.22 (6) Å^3	Irregular shape, colorless
Z = 4	0.65 × 0.30 × 0.20 mm
F(000) = 840

Data collection

Siemens SMART CCD diffractometer	7394 independent reflections
Radiation source: fine-focus sealed tube	5861 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 32.9°, θmin = 1.8°
Absorption correction: multi-scan (SADABS, Sheldrick, 2001)	h = −17→17
Tmin = 0.939, Tmax = 0.981	k = −14→14
33473 measured reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0586P)^2 + 0.5426P] where P = (Fo^2 + 2Fc^2)/3
7394 reflections	(Δ/σ)max < 0.001
286 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Experimental. Data were collected at 183 K using a Siemens SMART CCD diffractometer equipped with a Siemens LT-2 A low temperature device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 15 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 8192 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995). The data were empirically corrected for absorption and other effects using SADABS (Sheldrick, 2001) based on the method of Blessing (1995).

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. The structure was solved by direct methods and refined by full-matrix least squares on all F² data using SHELXTL (Bruker, 1997). All non-H atoms were refined anisotropically.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.00372 (7)	0.26496 (8)	0.25618 (4)	0.02953 (17)
O2	0.10719 (7)	0.15028 (7)	0.38367 (4)	0.02695 (15)
O3	0.29718 (7)	0.27099 (8)	0.46848 (4)	0.03178 (17)
O4	0.38019 (7)	0.69798 (8)	0.33437 (4)	0.02838 (16)
H4	0.4048	0.7708	0.3183	0.053 (5)*
O5	0.48713 (9)	0.44577 (10)	0.16854 (5)	0.0444 (2)
H5	0.4720	0.5075	0.1361	0.062 (5)*
O6	0.39378 (6)	0.71484 (7)	0.18345 (4)	0.02091 (13)
O7	0.27690 (7)	0.93525 (8)	0.21872 (5)	0.03244 (18)
O8	0.36330 (8)	0.62600 (9)	0.04555 (4)	0.03223 (18)
C1	0.24515 (8)	0.50809 (9)	0.30875 (5)	0.02041 (17)
C2	0.14171 (8)	0.45040 (10)	0.26748 (5)	0.02254 (18)
H2	0.1036	0.4915	0.2223	0.034 (4)*
C3	0.09503 (8)	0.33186 (10)	0.29329 (5)	0.02154 (17)
C4	0.14994 (8)	0.27274 (9)	0.36096 (5)	0.02125 (17)
C5	0.25209 (8)	0.33381 (10)	0.40260 (5)	0.02236 (17)
C6	0.30055 (8)	0.45055 (10)	0.37606 (5)	0.02256 (18)
H6	0.3707	0.4904	0.4037	0.036 (4)*
C7	−0.04562 (11)	0.30136 (15)	0.18097 (6)	0.0378 (3)
H7A	−0.0761	0.3965	0.1776	0.049 (4)*
H7B	−0.1080	0.2372	0.1582	0.055 (5)*
H7C	0.0185	0.2954	0.1556	0.040 (4)*
C8	0.40235 (10)	0.32813 (14)	0.51333 (7)	0.0365 (3)
H8A	0.4649	0.3243	0.4866	0.049 (4)*
H8B	0.4251	0.2740	0.5586	0.045 (4)*
H8C	0.3887	0.4249	0.5253	0.049 (4)*
C9	0.29599 (8)	0.63374 (10)	0.27772 (5)	0.02065 (17)
H9	0.2316	0.7017	0.2597	0.028 (3)*
C10	0.34869 (8)	0.59131 (9)	0.21281 (5)	0.02028 (17)
H10	0.2865	0.5482	0.1738	0.025 (3)*
C11	0.45136 (10)	0.49227 (12)	0.23274 (6)	0.0319 (2)
H11A	0.5174	0.5397	0.2659	0.040 (4)*
H11B	0.4291	0.4111	0.2591	0.042 (4)*
C12	0.31469 (8)	0.78403 (10)	0.12923 (5)	0.02170 (17)
C13	0.25505 (9)	0.90160 (11)	0.14603 (6)	0.0267 (2)
C14	0.17973 (11)	0.97455 (13)	0.08976 (7)	0.0376 (3)
H14	0.1388	1.0540	0.1007	0.058 (5)*
C15	0.16578 (11)	0.92945 (15)	0.01808 (8)	0.0422 (3)
H15	0.1147	0.9790	−0.0199	0.059 (5)*
C16	0.22431 (11)	0.81390 (14)	0.00036 (6)	0.0375 (3)
H16	0.2136	0.7850	−0.0492	0.047 (4)*
C17	0.29933 (9)	0.74021 (11)	0.05620 (5)	0.02623 (19)
C18	0.23050 (16)	1.06279 (15)	0.23917 (10)	0.0539 (4)
H18A	0.2574	1.1402	0.2132	0.058 (5)*
H18B	0.2573	1.0767	0.2921	0.069 (6)*
H18C	0.1451	1.0589	0.2262	0.058 (5)*
C19	0.33984 (14)	0.56785 (14)	−0.02728 (6)	0.0432 (3)
H19A	0.2571	0.5428	−0.0423	0.053 (5)*
H19B	0.3878	0.4847	−0.0275	0.061 (5)*
H19C	0.3586	0.6366	−0.0615	0.045 (4)*
C20	0.02895 (14)	0.16976 (15)	0.43106 (9)	0.0464 (3)
H20A	0.0702	0.2156	0.4762	0.076 (6)*
H20B	−0.0002	0.0793	0.4430	0.055 (5)*
H20C	−0.0368	0.2278	0.4065	0.075 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0262 (3)	0.0334 (4)	0.0260 (3)	−0.0101 (3)	−0.0004 (3)	0.0032 (3)
O2	0.0318 (4)	0.0198 (3)	0.0305 (4)	−0.0029 (3)	0.0095 (3)	0.0032 (3)
O3	0.0352 (4)	0.0289 (4)	0.0261 (4)	−0.0035 (3)	−0.0039 (3)	0.0079 (3)
O4	0.0394 (4)	0.0256 (4)	0.0211 (3)	−0.0129 (3)	0.0089 (3)	−0.0042 (3)
O5	0.0630 (6)	0.0457 (5)	0.0288 (4)	0.0324 (5)	0.0192 (4)	0.0047 (4)
O6	0.0193 (3)	0.0236 (3)	0.0192 (3)	−0.0003 (2)	0.0030 (2)	0.0013 (2)
O7	0.0367 (4)	0.0259 (4)	0.0369 (4)	0.0050 (3)	0.0129 (3)	−0.0039 (3)
O8	0.0465 (5)	0.0305 (4)	0.0194 (3)	−0.0002 (3)	0.0067 (3)	−0.0021 (3)
C1	0.0222 (4)	0.0177 (4)	0.0218 (4)	0.0004 (3)	0.0060 (3)	−0.0005 (3)
C2	0.0228 (4)	0.0216 (4)	0.0222 (4)	−0.0001 (3)	0.0031 (3)	0.0026 (3)
C3	0.0200 (4)	0.0216 (4)	0.0223 (4)	−0.0010 (3)	0.0034 (3)	−0.0014 (3)
C4	0.0243 (4)	0.0172 (4)	0.0227 (4)	−0.0001 (3)	0.0064 (3)	0.0009 (3)
C5	0.0245 (4)	0.0200 (4)	0.0213 (4)	0.0016 (3)	0.0026 (3)	0.0013 (3)
C6	0.0230 (4)	0.0206 (4)	0.0230 (4)	−0.0009 (3)	0.0028 (3)	−0.0010 (3)
C7	0.0338 (6)	0.0487 (7)	0.0263 (5)	−0.0139 (5)	−0.0026 (4)	0.0055 (5)
C8	0.0318 (5)	0.0404 (6)	0.0309 (5)	−0.0001 (5)	−0.0063 (4)	0.0056 (5)
C9	0.0231 (4)	0.0183 (4)	0.0212 (4)	−0.0005 (3)	0.0063 (3)	−0.0008 (3)
C10	0.0236 (4)	0.0182 (4)	0.0185 (4)	0.0020 (3)	0.0038 (3)	0.0003 (3)
C11	0.0393 (6)	0.0346 (5)	0.0233 (5)	0.0182 (5)	0.0100 (4)	0.0041 (4)
C12	0.0209 (4)	0.0215 (4)	0.0221 (4)	−0.0014 (3)	0.0036 (3)	0.0037 (3)
C13	0.0242 (4)	0.0237 (4)	0.0330 (5)	0.0000 (3)	0.0079 (4)	0.0045 (4)
C14	0.0321 (5)	0.0310 (5)	0.0499 (7)	0.0070 (4)	0.0095 (5)	0.0164 (5)
C15	0.0344 (6)	0.0453 (7)	0.0428 (7)	0.0015 (5)	−0.0002 (5)	0.0237 (6)
C16	0.0410 (6)	0.0424 (6)	0.0246 (5)	−0.0060 (5)	−0.0020 (4)	0.0112 (5)
C17	0.0297 (5)	0.0265 (5)	0.0216 (4)	−0.0051 (4)	0.0040 (3)	0.0040 (3)
C18	0.0686 (10)	0.0365 (7)	0.0635 (10)	0.0178 (7)	0.0295 (8)	−0.0059 (6)
C19	0.0679 (9)	0.0379 (6)	0.0231 (5)	−0.0128 (6)	0.0093 (5)	−0.0082 (5)
C20	0.0544 (8)	0.0394 (7)	0.0555 (8)	−0.0057 (6)	0.0334 (7)	0.0052 (6)

Geometric parameters (Å, º)

O1—C3	1.3722 (11)	C8—H8A	0.9800
O1—C7	1.4278 (13)	C8—H8B	0.9800
O2—C4	1.3852 (11)	C8—H8C	0.9800
O2—C20	1.4281 (15)	C9—C10	1.5396 (13)
O3—C5	1.3695 (12)	C9—H9	1.0000
O3—C8	1.4388 (14)	C10—C11	1.5175 (13)
O4—C9	1.4198 (11)	C10—H10	1.0000
O4—H4	0.8400	C11—H11A	0.9900
O5—C11	1.4326 (13)	C11—H11B	0.9900
O5—H5	0.8400	C12—C17	1.4040 (14)
O6—C12	1.3837 (11)	C12—C13	1.4039 (14)
O6—C10	1.4589 (11)	C13—C14	1.4028 (15)
O7—C13	1.3668 (14)	C14—C15	1.386 (2)
O7—C18	1.4301 (15)	C14—H14	0.9500
O8—C17	1.3717 (14)	C15—C16	1.387 (2)
O8—C19	1.4430 (13)	C15—H15	0.9500
C1—C6	1.3969 (13)	C16—C17	1.4000 (15)
C1—C2	1.4007 (13)	C16—H16	0.9500
C1—C9	1.5213 (13)	C18—H18A	0.9800
C2—C3	1.3986 (13)	C18—H18B	0.9800
C2—H2	0.9500	C18—H18C	0.9800
C3—C4	1.4068 (13)	C19—H19A	0.9800
C4—C5	1.4053 (13)	C19—H19B	0.9800
C5—C6	1.4007 (13)	C19—H19C	0.9800
C6—H6	0.9500	C20—H20A	0.9800
C7—H7A	0.9800	C20—H20B	0.9800
C7—H7B	0.9800	C20—H20C	0.9800
C7—H7C	0.9800
C3—O1—C7	116.71 (8)	C11—C10—C9	114.34 (8)
C4—O2—C20	114.14 (9)	O6—C10—H10	109.2
C5—O3—C8	117.72 (9)	C11—C10—H10	109.2
C9—O4—H4	109.5	C9—C10—H10	109.2
C11—O5—H5	109.5	O5—C11—C10	110.96 (8)
C12—O6—C10	115.31 (7)	O5—C11—H11A	109.4
C13—O7—C18	118.23 (10)	C10—C11—H11A	109.4
C17—O8—C19	117.01 (9)	O5—C11—H11B	109.4
C6—C1—C2	120.78 (9)	C10—C11—H11B	109.4
C6—C1—C9	121.10 (8)	H11A—C11—H11B	108.0
C2—C1—C9	118.12 (8)	O6—C12—C17	119.24 (9)
C1—C2—C3	119.48 (9)	O6—C12—C13	120.69 (9)
C1—C2—H2	120.3	C17—C12—C13	119.97 (9)
C3—C2—H2	120.3	O7—C13—C12	115.03 (9)
O1—C3—C2	124.11 (9)	O7—C13—C14	125.13 (10)
O1—C3—C4	115.55 (8)	C12—C13—C14	119.83 (10)
C2—C3—C4	120.34 (8)	C13—C14—C15	119.25 (11)
O2—C4—C3	119.74 (8)	C13—C14—H14	120.4
O2—C4—C5	120.62 (8)	C15—C14—H14	120.4
C3—C4—C5	119.51 (9)	C16—C15—C14	121.77 (11)
O3—C5—C6	124.62 (9)	C16—C15—H15	119.1
O3—C5—C4	115.14 (8)	C14—C15—H15	119.1
C6—C5—C4	120.25 (9)	C15—C16—C17	119.36 (11)
C1—C6—C5	119.60 (9)	C15—C16—H16	120.3
C1—C6—H6	120.2	C17—C16—H16	120.3
C5—C6—H6	120.2	O8—C17—C12	115.35 (9)
O1—C7—H7A	109.5	O8—C17—C16	124.82 (10)
O1—C7—H7B	109.5	C12—C17—C16	119.82 (11)
H7A—C7—H7B	109.5	O7—C18—H18A	109.5
O1—C7—H7C	109.5	O7—C18—H18B	109.5
H7A—C7—H7C	109.5	H18A—C18—H18B	109.5
H7B—C7—H7C	109.5	O7—C18—H18C	109.5
O3—C8—H8A	109.5	H18A—C18—H18C	109.5
O3—C8—H8B	109.5	H18B—C18—H18C	109.5
H8A—C8—H8B	109.5	O8—C19—H19A	109.5
O3—C8—H8C	109.5	O8—C19—H19B	109.5
H8A—C8—H8C	109.5	H19A—C19—H19B	109.5
H8B—C8—H8C	109.5	O8—C19—H19C	109.5
O4—C9—C1	109.16 (7)	H19A—C19—H19C	109.5
O4—C9—C10	111.65 (8)	H19B—C19—H19C	109.5
C1—C9—C10	110.75 (7)	O2—C20—H20A	109.5
O4—C9—H9	108.4	O2—C20—H20B	109.5
C1—C9—H9	108.4	H20A—C20—H20B	109.5
C10—C9—H9	108.4	O2—C20—H20C	109.5
O6—C10—C11	105.52 (8)	H20A—C20—H20C	109.5
O6—C10—C9	109.11 (7)	H20B—C20—H20C	109.5
C6—C1—C2—C3	−1.51 (14)	C12—O6—C10—C9	−89.24 (9)
C9—C1—C2—C3	177.73 (8)	O4—C9—C10—O6	−59.56 (9)
C7—O1—C3—C2	13.75 (15)	C1—C9—C10—O6	178.58 (7)
C7—O1—C3—C4	−165.75 (10)	O4—C9—C10—C11	58.31 (11)
C1—C2—C3—O1	−178.02 (9)	C1—C9—C10—C11	−63.55 (11)
C1—C2—C3—C4	1.46 (14)	O6—C10—C11—O5	−66.51 (11)
C20—O2—C4—C3	−95.46 (12)	C9—C10—C11—O5	173.58 (9)
C20—O2—C4—C5	88.67 (12)	C10—O6—C12—C17	−85.36 (10)
O1—C3—C4—O2	3.71 (13)	C10—O6—C12—C13	98.22 (10)
C2—C3—C4—O2	−175.81 (9)	C18—O7—C13—C12	172.64 (11)
O1—C3—C4—C5	179.62 (9)	C18—O7—C13—C14	−7.40 (17)
C2—C3—C4—C5	0.10 (14)	O6—C12—C13—O7	−3.30 (13)
C8—O3—C5—C6	−0.60 (15)	C17—C12—C13—O7	−179.69 (9)
C8—O3—C5—C4	179.48 (10)	O6—C12—C13—C14	176.73 (9)
O2—C4—C5—O3	−5.83 (13)	C17—C12—C13—C14	0.34 (15)
C3—C4—C5—O3	178.29 (9)	O7—C13—C14—C15	179.74 (11)
O2—C4—C5—C6	174.24 (8)	C12—C13—C14—C15	−0.29 (17)
C3—C4—C5—C6	−1.63 (14)	C13—C14—C15—C16	0.02 (19)
C2—C1—C6—C5	0.00 (14)	C14—C15—C16—C17	0.21 (19)
C9—C1—C6—C5	−179.23 (8)	C19—O8—C17—C12	172.90 (10)
O3—C5—C6—C1	−178.33 (9)	C19—O8—C17—C16	−8.29 (16)
C4—C5—C6—C1	1.58 (14)	O6—C12—C17—O8	2.31 (13)
C6—C1—C9—O4	−16.15 (12)	C13—C12—C17—O8	178.76 (9)
C2—C1—C9—O4	164.61 (8)	O6—C12—C17—C16	−176.56 (9)
C6—C1—C9—C10	107.16 (10)	C13—C12—C17—C16	−0.11 (15)
C2—C1—C9—C10	−72.08 (10)	C15—C16—C17—O8	−178.91 (10)
C12—O6—C10—C11	147.47 (8)	C15—C16—C17—C12	−0.16 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5^i	0.84	2.09	2.8569 (11)	152
O4—H4···O6	0.84	2.56	2.8731 (10)	104
O4—H4···O7	0.84	2.64	3.1934 (12)	125
O5—H5···O6	0.84	2.45	2.8504 (11)	110
O5—H5···O8	0.84	2.20	2.9876 (12)	157
C6—H6···O4	0.95	2.40	2.7360 (12)	101
C9—H9···O7	1.00	2.47	3.0947 (12)	120
C11—H11A···O7^ii	0.99	2.58	3.1676 (14)	118
C19—H19C···O4^iii	0.98	2.58	3.5465 (15)	171

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+3/2, z−1/2.