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In the title compound, C20H26O8, the mol­ecules adopt a conformation in which the torsion angle C(aryl)—C—C—O(aryl­oxy) is −70.8 (2)° and the torsion angle C(aryl)—O—C—C(benzyl­ic) is −152.71 (18)°, leading to a C(aryl)...C(aryl) distance of 4.426 (3) Å. This distance is identical, within experimental error, to the calculated maximum value obtained when the torsion angle C(aryl)—O—C—C(benzyl­ic) is varied and the torsion angle C(aryl)—C—C—O(aryl­oxy) is kept constant. The angle between the aromatic ring planes is 64.13 (7)°. The conformation is compared with those of related lignin model compounds. The hydrogen-bonding pattern reveals intramolecular interactions, and the formation of centrosymmetric dimers and chains of mol­ecules by intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007865/ac6164sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007865/ac6164Isup2.hkl
Contains datablock I

CCDC reference: 270223

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.049
  • wR factor = 0.120
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A .. O1 .. 2.61 Ang. PLAT726_ALERT_1_C H...A Calc 2.41821, Rep 2.43000 Dev... 0.01 Ang. H8A -O5 1.555 1.555 PLAT728_ALERT_1_C D-H..A Calc 110.86, Rep 112.00 Dev... 1.14 Deg. O8 -H8A -O4 1.555 1.555 1.555 PLAT728_ALERT_1_C D-H..A Calc 155.30, Rep 154.00 Dev... 1.30 Deg. O8 -H8A -O5 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995) and SADABS (Sheldrick, 2002; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXTL.

erythro-2-(2,6-Dimethoxy-4-methylphenoxy)-1-(4-hydroxy-3,5- dimethoxyphenyl)propane-1,3-diol top
Crystal data top
C20H26O8Z = 2
Mr = 394.41F(000) = 420
Triclinic, P1Dx = 1.356 Mg m3
Hall symbol: -P 1Melting point = 420–422 K
a = 8.6930 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.8976 (2) ÅCell parameters from 4159 reflections
c = 13.1057 (3) Åθ = 1.6–25.5°
α = 73.852 (1)°µ = 0.11 mm1
β = 86.150 (1)°T = 173 K
γ = 83.062 (1)°Prism, colourless
V = 965.96 (4) Å30.24 × 0.12 × 0.08 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3607 independent reflections
Radiation source: fine-focus sealed tube2409 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 1010
Tmin = 0.975, Tmax = 0.992k = 1010
10905 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.3785P]
where P = (Fo2 + 2Fc2)/3
3607 reflections(Δ/σ)max < 0.001
261 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

Experimental. Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with a LT-2 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, 20 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 4159 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 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. 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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.74929 (19)0.31626 (18)0.79907 (13)0.0336 (4)
O20.9884 (2)0.20449 (17)0.91973 (13)0.0327 (4)
H2A1.04100.18900.97390.049*
O31.20416 (18)0.38230 (18)0.94010 (13)0.0345 (4)
O40.65180 (16)0.90028 (17)0.68637 (12)0.0237 (4)
O50.65548 (18)1.13536 (19)0.50803 (12)0.0332 (4)
O60.41150 (18)0.88773 (19)0.82912 (13)0.0347 (4)
O70.89908 (19)0.94500 (19)0.88914 (14)0.0338 (4)
H7A0.89931.04140.88330.051*
O80.9347 (2)0.8642 (2)0.58124 (13)0.0386 (5)
H8A0.85150.91290.55480.058*
C10.9447 (3)0.6773 (3)0.75319 (18)0.0248 (5)
C20.8366 (3)0.5799 (3)0.74325 (18)0.0269 (5)
H20.75290.62090.69690.032*
C30.8505 (3)0.4231 (3)0.80077 (18)0.0252 (5)
C40.9752 (3)0.3612 (2)0.86679 (17)0.0231 (5)
C51.0841 (3)0.4580 (3)0.87512 (18)0.0245 (5)
C61.0681 (3)0.6159 (3)0.81996 (18)0.0254 (5)
H61.14160.68240.82780.031*
C70.9296 (3)0.8506 (3)0.69182 (18)0.0273 (5)
H71.02240.89620.70690.033*
C80.7862 (2)0.9463 (3)0.72375 (18)0.0237 (5)
H80.79371.06060.68910.028*
C90.6210 (3)0.3727 (3)0.7312 (2)0.0406 (7)
H9A0.56230.46320.74960.061*
H9B0.55350.28900.74030.061*
H9C0.65920.40460.65710.061*
C101.3161 (3)0.4762 (3)0.9572 (2)0.0386 (6)
H10A1.36630.52650.88910.058*
H10B1.39430.40961.00500.058*
H10C1.26470.55730.98910.058*
C110.5262 (2)1.0153 (3)0.66575 (18)0.0224 (5)
C120.5235 (3)1.1349 (3)0.57048 (18)0.0258 (5)
C130.3936 (3)1.2437 (3)0.54675 (19)0.0304 (6)
H130.39181.32440.48160.036*
C140.2664 (3)1.2357 (3)0.61720 (19)0.0314 (6)
C150.2704 (3)1.1183 (3)0.71258 (19)0.0311 (6)
H150.18431.11300.76160.037*
C160.3995 (3)1.0087 (3)0.73664 (18)0.0259 (5)
C170.6645 (3)1.2631 (3)0.4143 (2)0.0410 (7)
H17A0.58681.25850.36470.062*
H17B0.76821.25550.38060.062*
H17C0.64471.36290.43320.062*
C180.3190 (3)0.9136 (3)0.9180 (2)0.0435 (7)
H18A0.33201.01770.92590.065*
H18B0.35170.83260.98260.065*
H18C0.20970.90840.90660.065*
C190.1238 (3)1.3521 (3)0.5894 (2)0.0452 (7)
H19A0.05451.34350.65240.068*0.50
H19B0.06981.32930.53300.068*0.50
H19C0.15461.45910.56460.068*0.50
H19D0.13141.41110.51430.068*0.50
H19E0.11621.42530.63370.068*0.50
H19F0.03141.29550.60210.068*0.50
C200.7640 (3)0.9206 (3)0.84382 (18)0.0277 (5)
H20A0.67600.99400.85870.033*
H20B0.73830.81190.87720.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0346 (9)0.0225 (9)0.0420 (10)0.0045 (7)0.0176 (8)0.0018 (8)
O20.0407 (10)0.0215 (9)0.0328 (10)0.0022 (7)0.0164 (8)0.0009 (7)
O30.0299 (9)0.0273 (9)0.0421 (11)0.0021 (7)0.0169 (8)0.0009 (8)
O40.0202 (8)0.0218 (8)0.0290 (9)0.0017 (7)0.0069 (7)0.0072 (7)
O50.0317 (9)0.0366 (10)0.0233 (9)0.0053 (8)0.0023 (7)0.0005 (8)
O60.0318 (9)0.0331 (9)0.0318 (10)0.0007 (8)0.0048 (8)0.0009 (8)
O70.0379 (10)0.0279 (9)0.0377 (10)0.0021 (8)0.0157 (8)0.0097 (8)
O80.0390 (11)0.0432 (11)0.0293 (10)0.0008 (9)0.0009 (8)0.0056 (8)
C10.0225 (12)0.0220 (12)0.0288 (13)0.0007 (10)0.0005 (10)0.0057 (10)
C20.0260 (13)0.0241 (12)0.0281 (13)0.0035 (10)0.0063 (10)0.0046 (10)
C30.0239 (12)0.0208 (12)0.0313 (13)0.0009 (10)0.0046 (10)0.0075 (10)
C40.0286 (13)0.0149 (11)0.0229 (12)0.0014 (9)0.0018 (10)0.0020 (9)
C50.0219 (12)0.0259 (12)0.0233 (12)0.0018 (10)0.0047 (10)0.0038 (10)
C60.0228 (12)0.0226 (12)0.0305 (13)0.0036 (10)0.0024 (10)0.0058 (10)
C70.0261 (13)0.0257 (13)0.0282 (13)0.0019 (10)0.0001 (10)0.0050 (10)
C80.0237 (12)0.0174 (11)0.0286 (13)0.0023 (9)0.0070 (10)0.0024 (10)
C90.0387 (15)0.0303 (14)0.0522 (18)0.0052 (12)0.0224 (13)0.0048 (13)
C100.0292 (14)0.0394 (15)0.0446 (16)0.0063 (12)0.0142 (12)0.0031 (13)
C110.0205 (12)0.0219 (12)0.0257 (12)0.0016 (9)0.0073 (10)0.0079 (10)
C120.0250 (12)0.0298 (13)0.0228 (12)0.0011 (10)0.0022 (10)0.0086 (10)
C130.0352 (14)0.0295 (13)0.0231 (13)0.0056 (11)0.0079 (11)0.0038 (11)
C140.0277 (13)0.0360 (14)0.0309 (14)0.0070 (11)0.0087 (11)0.0122 (12)
C150.0237 (13)0.0384 (14)0.0323 (14)0.0009 (11)0.0005 (11)0.0136 (12)
C160.0239 (12)0.0270 (13)0.0255 (13)0.0034 (10)0.0025 (10)0.0043 (10)
C170.0470 (16)0.0377 (15)0.0298 (15)0.0012 (13)0.0064 (12)0.0017 (12)
C180.0465 (16)0.0470 (17)0.0304 (15)0.0037 (14)0.0091 (13)0.0026 (13)
C190.0355 (15)0.0516 (17)0.0447 (17)0.0170 (13)0.0099 (13)0.0143 (14)
C200.0295 (13)0.0256 (13)0.0285 (13)0.0025 (10)0.0044 (11)0.0073 (10)
Geometric parameters (Å, º) top
O1—C31.377 (3)C9—H9A0.9800
O1—C91.427 (3)C9—H9B0.9800
O2—C41.368 (2)C9—H9C0.9800
O2—H2A0.8400C10—H10A0.9800
O3—C51.378 (3)C10—H10B0.9800
O3—C101.423 (3)C10—H10C0.9800
O4—C111.388 (2)C11—C161.389 (3)
O4—C81.441 (3)C11—C121.397 (3)
O5—C121.364 (3)C12—C131.386 (3)
O5—C171.428 (3)C13—C141.388 (3)
O6—C161.380 (3)C13—H130.9500
O6—C181.427 (3)C14—C151.388 (3)
O7—C201.416 (3)C14—C191.511 (3)
O7—H7A0.8400C15—C161.386 (3)
O8—C71.418 (3)C15—H150.9500
O8—H8A0.8400C17—H17A0.9800
C1—C21.389 (3)C17—H17B0.9800
C1—C61.390 (3)C17—H17C0.9800
C1—C71.522 (3)C18—H18A0.9800
C2—C31.384 (3)C18—H18B0.9800
C2—H20.9500C18—H18C0.9800
C3—C41.394 (3)C19—H19A0.9800
C4—C51.383 (3)C19—H19B0.9800
C5—C61.385 (3)C19—H19C0.9800
C6—H60.9500C19—H19D0.9800
C7—C81.526 (3)C19—H19E0.9800
C7—H71.0000C19—H19F0.9800
C8—C201.528 (3)C20—H20A0.9900
C8—H81.0000C20—H20B0.9900
C3—O1—C9116.76 (17)H10A—C10—H10C109.5
C4—O2—H2A109.5H10B—C10—H10C109.5
C5—O3—C10117.22 (18)C16—C11—O4120.7 (2)
C11—O4—C8115.02 (16)C16—C11—C12119.4 (2)
C12—O5—C17117.47 (18)O4—C11—C12119.9 (2)
C16—O6—C18115.87 (18)O5—C12—C13125.0 (2)
C20—O7—H7A109.5O5—C12—C11115.07 (19)
C7—O8—H8A109.5C13—C12—C11119.9 (2)
C2—C1—C6119.6 (2)C14—C13—C12120.7 (2)
C2—C1—C7120.7 (2)C14—C13—H13119.7
C6—C1—C7119.7 (2)C12—C13—H13119.7
C3—C2—C1120.1 (2)C13—C14—C15119.4 (2)
C3—C2—H2120.0C13—C14—C19120.3 (2)
C1—C2—H2120.0C15—C14—C19120.4 (2)
O1—C3—C2125.3 (2)C16—C15—C14120.3 (2)
O1—C3—C4114.40 (19)C16—C15—H15119.8
C2—C3—C4120.3 (2)C14—C15—H15119.8
O2—C4—C5121.8 (2)O6—C16—C11115.85 (19)
O2—C4—C3118.8 (2)O6—C16—C15123.7 (2)
C5—C4—C3119.46 (19)C11—C16—C15120.4 (2)
O3—C5—C6125.5 (2)O5—C17—H17A109.5
O3—C5—C4114.09 (19)O5—C17—H17B109.5
C6—C5—C4120.4 (2)H17A—C17—H17B109.5
C5—C6—C1120.1 (2)O5—C17—H17C109.5
C5—C6—H6119.9H17A—C17—H17C109.5
C1—C6—H6119.9H17B—C17—H17C109.5
O8—C7—C1109.34 (19)O6—C18—H18A109.5
O8—C7—C8111.09 (18)O6—C18—H18B109.5
C1—C7—C8114.07 (19)H18A—C18—H18B109.5
O8—C7—H7107.3O6—C18—H18C109.5
C1—C7—H7107.3H18A—C18—H18C109.5
C8—C7—H7107.3H18B—C18—H18C109.5
O4—C8—C20107.87 (17)C14—C19—H19A109.5
O4—C8—C7108.24 (17)C14—C19—H19B109.5
C20—C8—C7113.42 (18)H19A—C19—H19B109.5
O4—C8—H8109.1C14—C19—H19C109.5
C20—C8—H8109.1H19A—C19—H19C109.5
C7—C8—H8109.1H19B—C19—H19C109.5
O1—C9—H9A109.5C14—C19—H19D109.5
O1—C9—H9B109.5C14—C19—H19E109.5
H9A—C9—H9B109.5H19D—C19—H19E109.5
O1—C9—H9C109.5C14—C19—H19F109.5
H9A—C9—H9C109.5O7—C20—C8111.56 (19)
H9B—C9—H9C109.5O7—C20—H20A109.3
O3—C10—H10A109.5C8—C20—H20A109.3
O3—C10—H10B109.5O7—C20—H20B109.3
H10A—C10—H10B109.5C8—C20—H20B109.3
O3—C10—H10C109.5H20A—C20—H20B108.0
C6—C1—C2—C30.9 (3)C1—C7—C8—O470.8 (2)
C7—C1—C2—C3179.0 (2)O8—C7—C8—C20173.04 (18)
C9—O1—C3—C20.8 (3)C1—C7—C8—C2048.9 (3)
C9—O1—C3—C4178.8 (2)C8—O4—C11—C16103.0 (2)
C1—C2—C3—O1178.7 (2)C8—O4—C11—C1280.0 (2)
C1—C2—C3—C41.7 (4)C17—O5—C12—C134.1 (3)
O1—C3—C4—O21.9 (3)C17—O5—C12—C11174.5 (2)
C2—C3—C4—O2177.8 (2)C16—C11—C12—O5177.5 (2)
O1—C3—C4—C5179.7 (2)O4—C11—C12—O55.5 (3)
C2—C3—C4—C50.6 (3)C16—C11—C12—C131.2 (3)
C10—O3—C5—C64.1 (3)O4—C11—C12—C13175.7 (2)
C10—O3—C5—C4176.6 (2)O5—C12—C13—C14178.1 (2)
O2—C4—C5—O30.2 (3)C11—C12—C13—C140.5 (4)
C3—C4—C5—O3178.1 (2)C12—C13—C14—C150.6 (4)
O2—C4—C5—C6179.6 (2)C12—C13—C14—C19178.4 (2)
C3—C4—C5—C61.2 (3)C13—C14—C15—C160.9 (4)
O3—C5—C6—C1177.3 (2)C19—C14—C15—C16178.1 (2)
C4—C5—C6—C11.9 (3)C18—O6—C16—C11155.3 (2)
C2—C1—C6—C50.8 (3)C18—O6—C16—C1525.3 (3)
C7—C1—C6—C5179.2 (2)O4—C11—C16—O63.4 (3)
C2—C1—C7—O860.2 (3)C12—C11—C16—O6179.65 (19)
C6—C1—C7—O8119.8 (2)O4—C11—C16—C15176.0 (2)
C2—C1—C7—C864.8 (3)C12—C11—C16—C150.9 (3)
C6—C1—C7—C8115.2 (2)C14—C15—C16—O6179.2 (2)
C11—O4—C8—C2084.2 (2)C14—C15—C16—C110.1 (4)
C11—O4—C8—C7152.71 (18)O4—C8—C20—O7172.91 (16)
O8—C7—C8—O453.4 (2)C7—C8—C20—O753.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O30.842.292.666 (2)108
O2—H2A···O7i0.841.922.676 (2)148
O7—H7A···O1ii0.842.613.316 (2)142
O7—H7A···O2ii0.841.912.662 (2)149
O8—H8A···O40.842.352.766 (2)112
O8—H8A···O50.842.433.201 (2)154
C2—H2···O40.952.503.022 (3)114
C19—H19B···O8iii0.982.593.428 (3)144
C20—H20B···O3i0.992.573.323 (3)132
Symmetry codes: (i) x+2, y+1, z+2; (ii) x, y+1, z; (iii) x+1, y+2, z+1.
Hydrogen-bonding geometry (Å, °) top
LabelD—H···AD—HH···AD···AD—H···A
[a]O2—H2A···O30.842.292.666 (2)108
[b]O2—H2A···O7i0.841.922.676 (2)148
[c]O7—H7A···O1ii0.842.613.316 (2)142
[d]O7—H7A···O2ii0.841.912.662 (2)149
[e]O8—H8A···O40.842.352.766 (2)112
[f]O8—H8A···O50.842.433.201 (3)154
[g]C2—H2···O40.952.503.022 (3)114
[h]C19—H19B···O8iii0.982.593.428 (3)144
[i]C20—H20B···O3i0.992.573.323 (3)132
Symmetry codes: (i) 2-x, 1-y, 2-z; (ii) x, 1+y, z; (iii) 1-x, 2-y, 1-z.
 

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