Download citation
Download citation
link to html
In the crystal structure of the title compound, C18H18O6, mol­ecules are connected by strong O—H...O hydrogen bonds to form centrosymmetric dimers. The angle Caryl—Cvinyl—Cvinyl is considerably larger (130.2°) than could be expected (ca 120°). This is attributed to steric interactions. The structure of the title compound provides a basis for the assignment of the stereoisomers of 3-(3,4-di­methoxy­phenyl)-2-(2-methoxy­phenoxy)-2-propenal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803029519/lh6154sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803029519/lh6154Isup2.hkl
Contains datablock I

CCDC reference: 234846

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.101
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: TEXSANTEXRAY (Molecular Structure Corporation, 1985); cell refinement: TEXSANTEXRAY; data reduction: TEXSANTEXRAY; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.

(Z)-3-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-2-propenoic acid top
Crystal data top
C18H18O6F(000) = 696
Mr = 330.32Dx = 1.331 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 8.920 (7) Åθ = 18.6–23.1°
b = 12.053 (6) ŵ = 0.10 mm1
c = 15.658 (6) ÅT = 296 K
β = 101.70 (4)°Prism, light yellow
V = 1648.4 (16) Å30.60 × 0.50 × 0.30 mm
Z = 4
Data collection top
Rigaku AFC-6
diffractometer
Rint = 0.016
Radiation source: normal-focus rotating anodeθmax = 25.0°, θmin = 2.2°
Graphite monochromatorh = 010
2θω scansk = 014
3100 measured reflectionsl = 1818
2901 independent reflections3 standard reflections every 150 reflections
1919 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.0335P)2 + 0.3604P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2901 reflectionsΔρmax = 0.21 e Å3
240 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0178 (15)
Special details top

Experimental. Data were collected at room temperature using a Rigaku AFC6R diffractometer. The data were collected using 2θ-ω-scan. Scans of (1.37 + 0.30tanθ) were made at a speed of 8.0ο/min in ω. The weak reflections (I<10.0σI) were rescanned (maximum 3 rescans) and the counts were accumulated to assure good counting statistics. Stationary bacground counts were recored on each side of the reflection·The ratio of peak counting time to backgroud counting time was 2:1. The crystal–to–detector distance was 400 mm.

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*/Ueq
C10.09822 (19)0.06378 (14)0.15409 (11)0.0434 (4)
C20.19625 (19)0.01258 (15)0.12446 (12)0.0450 (4)
H20.23570.07220.15970.044 (5)*
C30.2341 (2)0.00002 (15)0.04427 (12)0.0465 (4)
C40.1760 (2)0.09056 (15)0.00920 (12)0.0472 (4)
C50.0789 (2)0.16437 (15)0.01894 (12)0.0492 (5)
H50.03870.22350.01660.044 (5)*
C60.0405 (2)0.15131 (15)0.09991 (12)0.0481 (5)
H60.02500.20210.11810.056 (6)*
C70.05540 (19)0.05622 (15)0.23897 (12)0.0441 (4)
H70.01020.11180.25040.050 (5)*
C80.09545 (19)0.01783 (14)0.30291 (11)0.0430 (4)
C90.3805 (3)0.1671 (2)0.05904 (17)0.0795 (8)
H9A0.29490.21050.06840.105 (10)*
H9B0.44150.21050.02750.100 (8)*
H9C0.44150.14560.11430.109 (10)*
C100.1711 (3)0.18840 (19)0.14195 (15)0.0713 (6)
H10A0.06120.18860.15650.079 (7)*
H10B0.20660.25600.11220.077 (7)*
H10C0.21080.18270.19440.105 (9)*
C110.33326 (19)0.11361 (15)0.33168 (11)0.0433 (4)
C120.4065 (2)0.21467 (16)0.32813 (12)0.0514 (5)
C130.5622 (2)0.22145 (19)0.36244 (15)0.0658 (6)
H130.61340.28830.36040.088 (8)*
C140.6415 (2)0.1291 (2)0.39975 (16)0.0707 (6)
H140.74610.13430.42230.095 (8)*
C150.5684 (2)0.0303 (2)0.40394 (15)0.0671 (6)
H150.62230.03100.43010.092 (8)*
C160.4125 (2)0.02229 (17)0.36861 (13)0.0560 (5)
H160.36210.04500.37010.075 (7)*
C170.3793 (3)0.40837 (19)0.2980 (2)0.0796 (7)
H17A0.41370.42600.35860.129 (12)*
H17B0.30270.46080.27180.120 (11)*
H17C0.46430.41160.26900.113 (10)*
C180.0490 (2)0.01075 (15)0.38762 (12)0.0444 (4)
O10.32630 (16)0.07083 (12)0.01010 (9)0.0636 (4)
O20.22250 (16)0.09634 (12)0.08689 (9)0.0610 (4)
O30.17836 (13)0.11280 (10)0.29338 (8)0.0459 (3)
O40.31587 (16)0.29951 (11)0.28993 (10)0.0716 (4)
O50.09173 (15)0.08234 (11)0.44459 (8)0.0556 (4)
O60.03502 (17)0.07398 (11)0.39865 (10)0.0603 (4)
H6A0.05560.07100.44730.129 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0377 (9)0.0434 (10)0.0473 (10)0.0015 (8)0.0045 (8)0.0046 (8)
C20.0407 (10)0.0458 (10)0.0473 (10)0.0012 (8)0.0066 (8)0.0003 (8)
C30.0405 (9)0.0493 (11)0.0497 (10)0.0008 (8)0.0095 (8)0.0044 (8)
C40.0459 (10)0.0489 (11)0.0456 (10)0.0095 (9)0.0061 (8)0.0017 (8)
C50.0488 (11)0.0441 (10)0.0520 (11)0.0006 (9)0.0040 (9)0.0035 (9)
C60.0449 (10)0.0441 (10)0.0537 (11)0.0003 (9)0.0062 (9)0.0028 (8)
C70.0373 (9)0.0447 (10)0.0503 (10)0.0002 (8)0.0084 (8)0.0061 (8)
C80.0375 (9)0.0437 (10)0.0477 (10)0.0019 (8)0.0086 (8)0.0053 (8)
C90.0874 (18)0.0756 (16)0.0825 (18)0.0362 (15)0.0336 (16)0.0110 (14)
C100.0863 (19)0.0669 (15)0.0627 (14)0.0026 (13)0.0201 (13)0.0165 (12)
C110.0385 (9)0.0526 (11)0.0391 (9)0.0030 (8)0.0088 (7)0.0042 (8)
C120.0478 (11)0.0528 (12)0.0535 (11)0.0056 (9)0.0100 (9)0.0021 (9)
C130.0487 (12)0.0647 (14)0.0818 (15)0.0143 (11)0.0080 (11)0.0081 (12)
C140.0440 (12)0.0793 (16)0.0842 (16)0.0040 (12)0.0024 (11)0.0125 (13)
C150.0496 (12)0.0698 (15)0.0777 (15)0.0077 (11)0.0028 (11)0.0002 (12)
C160.0452 (11)0.0564 (12)0.0654 (13)0.0010 (10)0.0087 (9)0.0026 (10)
C170.0782 (17)0.0530 (14)0.109 (2)0.0128 (13)0.0231 (16)0.0118 (14)
C180.0383 (9)0.0438 (10)0.0517 (11)0.0015 (8)0.0099 (8)0.0031 (9)
O10.0675 (9)0.0671 (9)0.0620 (9)0.0190 (8)0.0272 (7)0.0070 (7)
O20.0701 (9)0.0637 (9)0.0533 (8)0.0008 (7)0.0220 (7)0.0089 (7)
O30.0393 (6)0.0470 (7)0.0501 (7)0.0046 (6)0.0060 (5)0.0052 (6)
O40.0592 (9)0.0513 (9)0.0983 (12)0.0099 (7)0.0016 (8)0.0104 (8)
O50.0628 (8)0.0533 (8)0.0546 (8)0.0068 (7)0.0207 (7)0.0058 (6)
O60.0694 (9)0.0572 (8)0.0606 (9)0.0157 (7)0.0282 (7)0.0023 (7)
Geometric parameters (Å, º) top
C1—C61.386 (2)C10—H10B0.9600
C1—C21.411 (2)C10—H10C0.9600
C1—C71.458 (3)C11—C161.371 (3)
C2—C31.373 (3)C11—C121.389 (3)
C2—H20.9300C11—O31.390 (2)
C3—O11.368 (2)C12—O41.364 (2)
C3—C41.409 (3)C12—C131.386 (3)
C4—O21.364 (2)C13—C141.384 (3)
C4—C51.375 (3)C13—H130.9300
C5—C61.388 (3)C14—C151.365 (3)
C5—H50.9300C14—H140.9300
C6—H60.9300C15—C161.392 (3)
C7—C81.335 (2)C15—H150.9300
C7—H70.9300C16—H160.9300
C8—O31.387 (2)C17—O41.424 (3)
C8—C181.470 (3)C17—H17A0.9600
C9—O11.421 (3)C17—H17B0.9600
C9—H9A0.9600C17—H17C0.9600
C9—H9B0.9600C18—O51.244 (2)
C9—H9C0.9600C18—O61.299 (2)
C10—O21.423 (2)O6—H6A0.8200
C10—H10A0.9600
C6—C1—C2118.25 (17)H10A—C10—H10C109.5
C6—C1—C7118.17 (16)H10B—C10—H10C109.5
C2—C1—C7123.58 (17)C16—C11—C12120.96 (17)
C3—C2—C1120.80 (18)C16—C11—O3123.96 (16)
C3—C2—H2119.6C12—C11—O3115.05 (16)
C1—C2—H2119.6O4—C12—C13125.72 (18)
O1—C3—C2124.58 (17)O4—C12—C11115.67 (17)
O1—C3—C4115.41 (16)C13—C12—C11118.61 (19)
C2—C3—C4120.01 (17)C12—C13—C14120.2 (2)
O2—C4—C5125.29 (17)C12—C13—H13119.9
O2—C4—C3115.34 (16)C14—C13—H13119.9
C5—C4—C3119.37 (17)C15—C14—C13120.9 (2)
C4—C5—C6120.50 (18)C15—C14—H14119.6
C4—C5—H5119.7C13—C14—H14119.6
C6—C5—H5119.7C14—C15—C16119.3 (2)
C5—C6—C1121.05 (18)C14—C15—H15120.3
C5—C6—H6119.5C16—C15—H15120.3
C1—C6—H6119.5C11—C16—C15120.0 (2)
C8—C7—C1130.22 (17)C11—C16—H16120.0
C8—C7—H7114.9C15—C16—H16120.0
C1—C7—H7114.9O4—C17—H17A109.5
C7—C8—O3122.59 (16)O4—C17—H17B109.5
C7—C8—C18123.81 (16)H17A—C17—H17B109.5
O3—C8—C18113.51 (15)O4—C17—H17C109.5
O1—C9—H9A109.5H17A—C17—H17C109.5
O1—C9—H9B109.5H17B—C17—H17C109.5
H9A—C9—H9B109.5O5—C18—O6123.46 (17)
O1—C9—H9C109.5O5—C18—C8120.34 (16)
H9A—C9—H9C109.5O6—C18—C8116.19 (16)
H9B—C9—H9C109.5C3—O1—C9117.71 (16)
O2—C10—H10A109.5C4—O2—C10117.47 (16)
O2—C10—H10B109.5C8—O3—C11117.66 (13)
H10A—C10—H10B109.5C12—O4—C17117.54 (18)
O2—C10—H10C109.5C18—O6—H6A109.5
C6—C1—C2—C30.4 (3)O4—C12—C13—C14179.9 (2)
C7—C1—C2—C3179.01 (17)C11—C12—C13—C140.4 (3)
C1—C2—C3—O1179.02 (17)C12—C13—C14—C150.4 (4)
C1—C2—C3—C40.6 (3)C13—C14—C15—C161.2 (4)
O1—C3—C4—O21.4 (2)C12—C11—C16—C150.6 (3)
C2—C3—C4—O2179.01 (16)O3—C11—C16—C15178.69 (18)
O1—C3—C4—C5178.24 (16)C14—C15—C16—C111.3 (3)
C2—C3—C4—C51.4 (3)C7—C8—C18—O5179.37 (17)
O2—C4—C5—C6179.21 (17)O3—C8—C18—O54.1 (2)
C3—C4—C5—C61.2 (3)C7—C8—C18—O60.4 (3)
C4—C5—C6—C10.3 (3)O3—C8—C18—O6176.94 (15)
C2—C1—C6—C50.6 (3)C2—C3—O1—C93.3 (3)
C7—C1—C6—C5178.89 (16)C4—C3—O1—C9176.27 (19)
C6—C1—C7—C8179.26 (18)C5—C4—O2—C102.5 (3)
C2—C1—C7—C80.2 (3)C3—C4—O2—C10177.91 (17)
C1—C7—C8—O37.4 (3)C7—C8—O3—C11103.1 (2)
C1—C7—C8—C18176.45 (17)C18—C8—O3—C1180.32 (18)
C16—C11—C12—O4179.95 (17)C16—C11—O3—C88.4 (2)
O3—C11—C12—O41.8 (2)C12—C11—O3—C8173.35 (15)
C16—C11—C12—C130.3 (3)C13—C12—O4—C1710.7 (3)
O3—C11—C12—C13178.00 (17)C11—C12—O4—C17169.55 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···O5i0.821.792.607 (2)173
C2—H2···O30.932.312.941 (2)125
C7—H7···O60.932.422.787 (2)103
Symmetry code: (i) x, y, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds