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In the crystals of the lignin model, threo-1-(3,4-di­methoxy­phenyl)-2-(2-methoxy­phenoxy)-1,3-propane­diol, C18H22O6, the mol­ecules adopt a conformation in which the Caryl...Caryl distance between the bulky 2-methoxy­phenyl and 3,4-di­methoxy­phenyl groups, 4.871 (3) Å, is very close to the calculated maximum value, 4.88 Å. The torsion angle between the 2-methoxy­phenoxy group and the 3,4-di­methoxy­phenyl group is 176.02 (19)°. Intermolecular hydrogen bonding between benzyl­ic hydroxyl groups results in a helical arrangement of the mol­ecules in the crystals.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004828/cm6003sup1.cif
Contains datablocks I, n

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004828/cm6003Isup2.hkl
Contains datablock I

CCDC reference: 183804

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.065
  • wR factor = 0.175
  • Data-to-parameter ratio = 13.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2001); 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.

threo-1-(3,4-Dimethoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol top
Crystal data top
C18H22O6F(000) = 712
Mr = 334.36Dx = 1.363 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.7932 (2) ÅCell parameters from 6757 reflections
b = 4.6909 (1) Åθ = 2.1–26.6°
c = 25.2138 (3) ŵ = 0.10 mm1
β = 93.06°T = 183 K
V = 1629.06 (5) Å3Needle, colourless
Z = 40.55 × 0.05 × 0.05 mm
Data collection top
Siemens SMART CCD
diffractometer
3375 independent reflections
Radiation source: fine-focus sealed tube2422 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
ω scansθmax = 26.6°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1717
Tmin = 0.946, Tmax = 0.995k = 55
15921 measured reflectionsl = 3131
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0874P)2 + 1.0506P]
where P = (Fo2 + 2Fc2)/3
3375 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.39 e Å3
Special details top

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, 30 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 6757 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.

The data were empirically corrected for absorption and other effects using SADABS (Sheldrick, 2001) based on the method of Blessing (1995). 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.10205 (12)0.4087 (4)0.58500 (7)0.0344 (5)
O20.05841 (12)0.0413 (4)0.65620 (7)0.0329 (5)
O30.45036 (12)0.6377 (4)0.73276 (7)0.0269 (4)
H30.48380.78630.73730.038 (9)*
O40.45032 (14)0.6655 (5)0.56167 (8)0.0392 (5)
H40.49870.77430.56410.082 (15)*
O50.57763 (11)0.6548 (4)0.65344 (7)0.0258 (4)
O60.65691 (13)0.8499 (4)0.56783 (7)0.0339 (5)
C10.32228 (16)0.4609 (5)0.67451 (9)0.0227 (5)
C20.25725 (16)0.5123 (6)0.63083 (10)0.0240 (6)
H20.27360.64640.60450.019 (6)*
C30.17028 (16)0.3705 (6)0.62583 (10)0.0254 (6)
C40.14631 (16)0.1734 (5)0.66456 (10)0.0249 (6)
C50.20889 (17)0.1282 (6)0.70793 (10)0.0276 (6)
H50.19190.00210.73470.023 (7)*
C60.29690 (17)0.2718 (6)0.71281 (10)0.0267 (6)
H60.33980.23880.74290.039 (8)*
C70.1165 (2)0.6378 (7)0.55016 (11)0.0367 (7)
H7A0.12100.81610.57040.043 (9)*
H7B0.06180.64870.52380.056 (10)*
H7C0.17680.60780.53210.064 (11)*
C80.03223 (19)0.1590 (6)0.69495 (11)0.0325 (6)
H8A0.08310.30410.69950.040 (8)*
H8B0.02920.25040.68340.035 (8)*
H8C0.02470.06120.72880.032 (7)*
C90.41805 (16)0.6152 (6)0.67805 (9)0.0227 (5)
H90.40860.81130.66310.015 (6)*
C100.49589 (16)0.4630 (6)0.64805 (10)0.0239 (6)
H100.51280.27800.66590.027 (7)*
C110.47149 (18)0.4123 (6)0.58993 (10)0.0302 (6)
H11A0.52700.31590.57420.044 (9)*
H11B0.41480.28310.58610.044 (9)*
C120.66575 (16)0.5416 (6)0.64104 (10)0.0242 (5)
C130.71011 (17)0.6559 (6)0.59741 (10)0.0262 (6)
C140.80334 (18)0.5723 (7)0.58763 (11)0.0333 (7)
H140.83600.65630.55930.030 (7)*
C150.84903 (19)0.3667 (7)0.61903 (11)0.0357 (7)
H150.91310.30880.61200.034 (8)*
C160.80294 (18)0.2444 (7)0.66039 (11)0.0339 (7)
H160.83420.09900.68120.035 (8)*
C170.71054 (18)0.3352 (6)0.67141 (10)0.0287 (6)
H170.67840.25340.70010.026 (7)*
C180.6965 (2)0.9488 (8)0.52061 (11)0.0429 (8)
H18A0.75811.04640.52930.067 (11)*
H18B0.65101.08180.50260.042 (9)*
H18C0.70780.78670.49720.051 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0195 (9)0.0442 (13)0.0387 (10)0.0046 (8)0.0067 (7)0.0090 (9)
O20.0148 (8)0.0368 (11)0.0468 (11)0.0058 (8)0.0018 (7)0.0067 (9)
O30.0184 (9)0.0309 (11)0.0313 (9)0.0048 (8)0.0003 (7)0.0036 (8)
O40.0271 (10)0.0531 (14)0.0369 (11)0.0024 (10)0.0039 (8)0.0072 (10)
O50.0109 (8)0.0284 (10)0.0384 (10)0.0005 (7)0.0034 (7)0.0037 (8)
O60.0246 (9)0.0407 (12)0.0368 (10)0.0034 (8)0.0046 (7)0.0085 (9)
C10.0129 (10)0.0231 (13)0.0320 (13)0.0027 (9)0.0014 (9)0.0034 (11)
C20.0174 (11)0.0260 (14)0.0287 (13)0.0014 (10)0.0033 (9)0.0012 (11)
C30.0153 (11)0.0306 (14)0.0301 (13)0.0031 (10)0.0020 (9)0.0018 (11)
C40.0131 (11)0.0240 (13)0.0375 (14)0.0006 (10)0.0010 (9)0.0034 (11)
C50.0191 (12)0.0289 (14)0.0350 (14)0.0009 (11)0.0041 (10)0.0061 (12)
C60.0159 (11)0.0292 (14)0.0348 (14)0.0038 (10)0.0019 (10)0.0009 (12)
C70.0309 (15)0.0460 (19)0.0322 (15)0.0005 (13)0.0064 (11)0.0055 (14)
C80.0204 (12)0.0315 (15)0.0463 (16)0.0039 (11)0.0075 (11)0.0011 (13)
C90.0156 (11)0.0225 (13)0.0298 (13)0.0023 (10)0.0002 (9)0.0011 (11)
C100.0123 (11)0.0260 (13)0.0332 (13)0.0010 (10)0.0006 (9)0.0010 (11)
C110.0178 (12)0.0371 (16)0.0357 (14)0.0014 (11)0.0011 (10)0.0059 (13)
C120.0130 (11)0.0296 (14)0.0298 (13)0.0001 (10)0.0007 (9)0.0061 (11)
C130.0186 (11)0.0293 (14)0.0303 (13)0.0003 (10)0.0017 (9)0.0012 (12)
C140.0197 (12)0.0463 (18)0.0342 (14)0.0019 (12)0.0048 (10)0.0054 (13)
C150.0179 (12)0.0479 (18)0.0415 (15)0.0040 (12)0.0019 (11)0.0096 (14)
C160.0209 (12)0.0396 (17)0.0403 (15)0.0066 (12)0.0074 (11)0.0038 (14)
C170.0205 (12)0.0351 (16)0.0302 (13)0.0005 (11)0.0022 (10)0.0019 (12)
C180.0400 (17)0.052 (2)0.0368 (16)0.0009 (15)0.0030 (12)0.0110 (16)
Geometric parameters (Å, º) top
O1—C31.369 (3)C7—H7C0.9800
O1—C71.409 (3)C8—H8A0.9800
O2—C41.368 (3)C8—H8B0.9800
O2—C81.416 (3)C8—H8C0.9800
O3—C91.431 (3)C9—C101.524 (3)
O3—H30.8400C9—H91.0000
O4—C111.408 (3)C10—C111.505 (4)
O4—H40.8400C10—H101.0000
O5—C121.378 (3)C11—H11A0.9900
O5—C101.443 (3)C11—H11B0.9900
O6—C131.366 (3)C12—C171.362 (4)
O6—C181.414 (3)C12—C131.394 (4)
C1—C61.370 (4)C13—C141.379 (3)
C1—C21.404 (3)C14—C151.379 (4)
C1—C91.505 (3)C14—H140.9500
C2—C31.371 (3)C15—C161.375 (4)
C2—H20.9500C15—H150.9500
C3—C41.397 (4)C16—C171.386 (4)
C4—C51.373 (4)C16—H160.9500
C5—C61.388 (3)C17—H170.9500
C5—H50.9500C18—H18A0.9800
C6—H60.9500C18—H18B0.9800
C7—H7A0.9800C18—H18C0.9800
C7—H7B0.9800
C3—O1—C7117.0 (2)O3—C9—H9108.9
C4—O2—C8116.8 (2)C1—C9—H9108.9
C9—O3—H3109.5C10—C9—H9108.9
C11—O4—H4109.5O5—C10—C11108.9 (2)
C12—O5—C10115.63 (19)O5—C10—C9103.2 (2)
C13—O6—C18117.3 (2)C11—C10—C9115.5 (2)
C6—C1—C2119.2 (2)O5—C10—H10109.7
C6—C1—C9121.7 (2)C11—C10—H10109.7
C2—C1—C9119.1 (2)C9—C10—H10109.7
C3—C2—C1120.5 (2)O4—C11—C10112.9 (2)
C3—C2—H2119.7O4—C11—H11A109.0
C1—C2—H2119.7C10—C11—H11A109.0
O1—C3—C2124.6 (2)O4—C11—H11B109.0
O1—C3—C4115.7 (2)C10—C11—H11B109.0
C2—C3—C4119.7 (2)H11A—C11—H11B107.8
O2—C4—C5124.5 (2)C17—C12—O5121.7 (2)
O2—C4—C3115.7 (2)C17—C12—C13120.8 (2)
C5—C4—C3119.8 (2)O5—C12—C13117.4 (2)
C4—C5—C6120.3 (2)O6—C13—C14124.8 (2)
C4—C5—H5119.8O6—C13—C12116.2 (2)
C6—C5—H5119.8C14—C13—C12119.0 (2)
C5—C6—C1120.5 (2)C13—C14—C15119.9 (3)
C5—C6—H6119.8C13—C14—H14120.1
C1—C6—H6119.8C15—C14—H14120.1
O1—C7—H7A109.5C16—C15—C14120.8 (2)
O1—C7—H7B109.5C16—C15—H15119.6
H7A—C7—H7B109.5C14—C15—H15119.6
O1—C7—H7C109.5C15—C16—C17119.4 (3)
H7A—C7—H7C109.5C15—C16—H16120.3
H7B—C7—H7C109.5C17—C16—H16120.3
O2—C8—H8A109.5C12—C17—C16120.0 (3)
O2—C8—H8B109.5C12—C17—H17120.0
H8A—C8—H8B109.5C16—C17—H17120.0
O2—C8—H8C109.5O6—C18—H18A109.5
H8A—C8—H8C109.5O6—C18—H18B109.5
H8B—C8—H8C109.5H18A—C18—H18B109.5
O3—C9—C1108.66 (19)O6—C18—H18C109.5
O3—C9—C10108.77 (18)H18A—C18—H18C109.5
C1—C9—C10112.6 (2)H18B—C18—H18C109.5
C6—C1—C2—C31.5 (4)C12—O5—C10—C9165.07 (19)
C9—C1—C2—C3178.6 (2)O3—C9—C10—O563.5 (2)
C7—O1—C3—C29.5 (4)C1—C9—C10—O5176.02 (19)
C7—O1—C3—C4169.9 (2)O3—C9—C10—C11177.8 (2)
C1—C2—C3—O1179.3 (2)C1—C9—C10—C1157.3 (3)
C1—C2—C3—C40.0 (4)O5—C10—C11—O457.8 (3)
C8—O2—C4—C51.2 (4)C9—C10—C11—O457.7 (3)
C8—O2—C4—C3179.8 (2)C10—O5—C12—C1767.8 (3)
O1—C3—C4—O20.9 (3)C10—O5—C12—C13115.1 (3)
C2—C3—C4—O2179.7 (2)C18—O6—C13—C147.1 (4)
O1—C3—C4—C5177.8 (2)C18—O6—C13—C12174.2 (2)
C2—C3—C4—C51.6 (4)C17—C12—C13—O6176.4 (2)
O2—C4—C5—C6179.7 (2)O5—C12—C13—O66.5 (3)
C3—C4—C5—C61.7 (4)C17—C12—C13—C144.8 (4)
C4—C5—C6—C10.2 (4)O5—C12—C13—C14172.3 (2)
C2—C1—C6—C51.4 (4)O6—C13—C14—C15177.7 (3)
C9—C1—C6—C5178.7 (2)C12—C13—C14—C153.6 (4)
C6—C1—C9—O326.4 (3)C13—C14—C15—C160.4 (4)
C2—C1—C9—O3153.6 (2)C14—C15—C16—C171.8 (4)
C6—C1—C9—C1094.2 (3)O5—C12—C17—C16174.3 (2)
C2—C1—C9—C1085.9 (3)C13—C12—C17—C162.6 (4)
C12—O5—C10—C1171.7 (3)C15—C16—C17—C120.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O3i0.842.012.8293 (18)165
O4—H4···O60.842.212.974 (3)152
C7—H7A···O2ii0.982.603.406 (4)140
C15—H15···O2iii0.952.573.356 (3)140
C17—H17···O3iv0.952.583.492 (3)162
C18—H18B···O4v0.982.403.351 (4)165
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x+1, y1/2, z+3/2; (v) x+1, y+2, z+1.
 

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