Download citation
Download citation
link to html
The title compound, C18H18O6, was prepared by the reaction of 4-hydr­oxy-3-methoxy­benzaldehyde and 1,2-dibromo­ethane. There are one and a half mol­ecules in the asymmetric unit; one has C1 mol­ecular symmetry and the other Ci, with the centre of inversion at the mid-point of the aliphatic C-C bond. The ethyl­enedi­oxy groups are coplanar with the aromatic systems of the vanillin groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032861/kp6051sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032861/kp6051Isup2.hkl
Contains datablock I

CCDC reference: 289789

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.062
  • wR factor = 0.191
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C7 .. 6.65 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.26 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

4-[2-(4-Formyl-2-methoxyphenoxy)ethoxy]-3-methoxybenzaldehyde top
Crystal data top
C18H18O6F(000) = 1044
Mr = 330.32Dx = 1.373 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ynCell parameters from 4375 reflections
a = 14.692 (4) Åθ = 2.8–26.3°
b = 7.805 (2) ŵ = 0.10 mm1
c = 22.048 (6) ÅT = 294 K
β = 108.551 (4)°Prism, colourless
V = 2396.8 (11) Å30.30 × 0.24 × 0.22 mm
Z = 6
Data collection top
Bruker SMART CCD area-detector
diffractometer
4170 independent reflections
Radiation source: fine-focus sealed tube2809 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1710
Tmin = 0.960, Tmax = 0.978k = 98
11241 measured reflectionsl = 2326
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0898P)2 + 1.1951P]
where P = (Fo2 + 2Fc2)/3
4170 reflections(Δ/σ)max < 0.001
328 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.33 e Å3
Special details top

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 > 2 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
O10.73125 (13)0.6129 (2)0.95201 (8)0.0358 (5)
O20.60106 (12)0.3972 (2)1.04076 (7)0.0333 (4)
O30.82650 (15)0.8629 (2)0.92602 (9)0.0488 (6)
O40.90678 (18)0.6518 (3)0.72197 (10)0.0649 (7)
O50.51552 (14)0.1375 (2)1.06937 (8)0.0418 (5)
O60.44523 (18)0.3363 (3)1.27841 (10)0.0652 (7)
O70.93391 (13)0.3805 (2)0.04066 (8)0.0362 (5)
O80.83355 (15)0.1213 (2)0.05471 (9)0.0469 (6)
O90.80159 (17)0.4659 (3)0.28834 (10)0.0613 (7)
C10.76262 (17)0.5888 (3)0.90067 (11)0.0302 (6)
C20.81430 (18)0.7269 (3)0.88622 (11)0.0326 (6)
C30.84873 (19)0.7124 (3)0.83537 (11)0.0362 (6)
H30.88320.80230.82560.043*
C40.83229 (18)0.5637 (3)0.79829 (11)0.0353 (6)
C50.78274 (19)0.4311 (3)0.81308 (12)0.0370 (6)
H50.77280.33160.78860.044*
C60.74692 (18)0.4424 (3)0.86412 (12)0.0359 (6)
H60.71260.35170.87350.043*
C70.8650 (2)0.5457 (4)0.74105 (13)0.0434 (7)
H70.85160.44290.71860.052*
C80.8854 (3)1.0005 (4)0.91691 (16)0.0635 (10)
H8A0.94830.95790.92090.095*
H8B0.89011.08730.94860.095*
H8C0.85721.04870.87510.095*
C90.67984 (18)0.4744 (3)0.96822 (11)0.0306 (6)
H9A0.72000.37320.97950.037*
H9B0.62310.44660.93260.037*
C100.65239 (18)0.5365 (3)1.02446 (11)0.0310 (6)
H10A0.70910.56461.06000.037*
H10B0.61200.63751.01320.037*
C110.57300 (17)0.4173 (3)1.09334 (10)0.0281 (6)
C120.52692 (18)0.2742 (3)1.10936 (11)0.0304 (6)
C130.49662 (19)0.2828 (3)1.16230 (11)0.0349 (6)
H130.46710.18861.17390.042*
C140.51023 (19)0.4340 (3)1.19897 (11)0.0343 (6)
C150.55290 (18)0.5727 (3)1.18162 (12)0.0361 (6)
H150.56020.67341.20530.043*
C160.58550 (18)0.5653 (3)1.12926 (12)0.0347 (6)
H160.61570.65971.11840.042*
C170.4652 (3)0.0070 (4)1.08213 (15)0.0585 (9)
H17A0.49830.05031.12410.088*
H17B0.46200.09471.05100.088*
H17C0.40130.02671.07990.088*
C180.4809 (2)0.4468 (4)1.25641 (13)0.0451 (7)
H180.49110.55151.27770.054*
C190.89998 (17)0.3897 (3)0.09120 (11)0.0296 (6)
C200.91589 (18)0.5256 (3)0.13373 (12)0.0359 (6)
H200.95220.61900.12880.043*
C210.87782 (18)0.5219 (3)0.18343 (12)0.0360 (6)
H210.88930.61240.21240.043*
C220.82233 (18)0.3836 (3)0.19039 (11)0.0329 (6)
C230.80551 (19)0.2487 (3)0.14715 (11)0.0337 (6)
H230.76690.15770.15110.040*
C240.84544 (18)0.2482 (3)0.09845 (11)0.0310 (6)
C250.7811 (2)0.3749 (4)0.24300 (13)0.0433 (7)
H250.73510.29090.24040.052*
C260.7796 (3)0.0248 (4)0.06196 (17)0.0679 (11)
H26A0.81220.08080.10170.102*
H26B0.77340.10290.02720.102*
H26C0.71700.01090.06180.102*
C270.98484 (18)0.5254 (3)0.02818 (11)0.0333 (6)
H27A1.04040.55080.06490.040*
H27B0.94360.62550.01820.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0475 (11)0.0364 (10)0.0329 (9)0.0099 (8)0.0262 (8)0.0025 (8)
O20.0444 (11)0.0369 (10)0.0275 (9)0.0070 (8)0.0238 (8)0.0011 (7)
O30.0742 (14)0.0362 (11)0.0502 (12)0.0155 (10)0.0399 (11)0.0058 (9)
O40.0892 (18)0.0698 (15)0.0543 (13)0.0029 (13)0.0492 (13)0.0077 (12)
O50.0709 (14)0.0307 (9)0.0363 (10)0.0054 (9)0.0346 (10)0.0021 (8)
O60.0943 (18)0.0657 (15)0.0569 (14)0.0026 (13)0.0541 (13)0.0048 (12)
O70.0478 (11)0.0374 (10)0.0327 (9)0.0108 (8)0.0260 (8)0.0019 (8)
O80.0735 (14)0.0368 (10)0.0441 (11)0.0152 (10)0.0382 (10)0.0093 (8)
O90.0831 (17)0.0647 (14)0.0465 (12)0.0114 (12)0.0354 (12)0.0079 (11)
C10.0317 (13)0.0397 (14)0.0225 (11)0.0004 (11)0.0131 (10)0.0051 (10)
C20.0394 (15)0.0311 (13)0.0308 (13)0.0002 (11)0.0160 (11)0.0019 (10)
C30.0410 (15)0.0389 (15)0.0350 (13)0.0001 (12)0.0209 (12)0.0108 (11)
C40.0384 (15)0.0444 (15)0.0271 (12)0.0078 (12)0.0162 (11)0.0073 (11)
C50.0440 (16)0.0433 (15)0.0285 (13)0.0034 (13)0.0183 (12)0.0052 (11)
C60.0398 (15)0.0394 (14)0.0337 (13)0.0089 (12)0.0190 (12)0.0003 (11)
C70.0480 (17)0.0449 (16)0.0464 (16)0.0089 (14)0.0282 (14)0.0113 (13)
C80.097 (3)0.0413 (17)0.066 (2)0.0249 (18)0.045 (2)0.0083 (15)
C90.0343 (14)0.0354 (13)0.0272 (12)0.0047 (11)0.0168 (11)0.0036 (10)
C100.0348 (14)0.0358 (13)0.0278 (12)0.0042 (11)0.0174 (11)0.0036 (10)
C110.0298 (13)0.0354 (13)0.0219 (11)0.0037 (11)0.0122 (10)0.0011 (10)
C120.0387 (14)0.0314 (13)0.0257 (12)0.0034 (11)0.0166 (11)0.0020 (10)
C130.0432 (15)0.0366 (14)0.0319 (13)0.0048 (12)0.0220 (12)0.0090 (11)
C140.0404 (15)0.0410 (14)0.0252 (12)0.0108 (12)0.0158 (11)0.0023 (11)
C150.0422 (15)0.0382 (14)0.0312 (13)0.0003 (12)0.0165 (12)0.0076 (11)
C160.0360 (14)0.0367 (14)0.0357 (13)0.0059 (12)0.0173 (11)0.0020 (11)
C170.098 (3)0.0357 (16)0.0560 (19)0.0167 (16)0.0439 (19)0.0049 (14)
C180.0594 (19)0.0436 (16)0.0397 (15)0.0091 (15)0.0260 (14)0.0028 (13)
C190.0310 (13)0.0366 (13)0.0247 (12)0.0006 (11)0.0139 (10)0.0046 (10)
C200.0359 (15)0.0410 (15)0.0336 (13)0.0060 (12)0.0152 (11)0.0012 (11)
C210.0392 (15)0.0407 (14)0.0299 (13)0.0014 (12)0.0137 (11)0.0068 (11)
C220.0367 (14)0.0400 (14)0.0258 (12)0.0080 (12)0.0155 (11)0.0076 (11)
C230.0434 (15)0.0306 (13)0.0338 (13)0.0004 (11)0.0216 (12)0.0085 (11)
C240.0411 (15)0.0299 (13)0.0255 (12)0.0002 (11)0.0154 (11)0.0023 (10)
C250.0585 (19)0.0372 (15)0.0432 (16)0.0118 (13)0.0291 (14)0.0002 (13)
C260.113 (3)0.0415 (17)0.067 (2)0.0312 (19)0.055 (2)0.0164 (16)
C270.0346 (14)0.0382 (14)0.0310 (13)0.0051 (11)0.0161 (11)0.0048 (11)
Geometric parameters (Å, º) top
O1—C11.364 (3)C10—H10B0.9700
O1—C91.428 (3)C11—C161.379 (3)
O2—C111.358 (3)C11—C121.408 (3)
O2—C101.433 (3)C12—C131.377 (3)
O3—C21.352 (3)C13—C141.408 (4)
O3—C81.433 (3)C13—H130.9300
O4—C71.185 (3)C14—C151.365 (4)
O5—C121.360 (3)C14—C181.465 (4)
O5—C171.425 (3)C15—C161.385 (3)
O6—C181.190 (3)C15—H150.9300
O7—C191.360 (3)C16—H160.9300
O7—C271.430 (3)C17—H17A0.9600
O8—C241.355 (3)C17—H17B0.9600
O8—C261.426 (3)C17—H17C0.9600
O9—C251.185 (3)C18—H180.9300
C1—C61.375 (4)C19—C201.385 (3)
C1—C21.412 (3)C19—C241.403 (3)
C2—C31.373 (3)C20—C211.380 (4)
C3—C41.396 (4)C20—H200.9300
C3—H30.9300C21—C221.391 (4)
C4—C51.364 (4)C21—H210.9300
C4—C71.493 (4)C22—C231.389 (3)
C5—C61.388 (3)C22—C251.471 (4)
C5—H50.9300C23—C241.378 (3)
C6—H60.9300C23—H230.9300
C7—H70.9300C25—H250.9300
C8—H8A0.9600C26—H26A0.9600
C8—H8B0.9600C26—H26B0.9600
C8—H8C0.9600C26—H26C0.9600
C9—C101.501 (3)C27—C27i1.500 (5)
C9—H9A0.9700C27—H27A0.9700
C9—H9B0.9700C27—H27B0.9700
C10—H10A0.9700
C1—O1—C9116.68 (18)C14—C13—H13119.9
C11—O2—C10116.97 (18)C15—C14—C13119.8 (2)
C2—O3—C8117.3 (2)C15—C14—C18118.4 (2)
C12—O5—C17117.21 (19)C13—C14—C18121.8 (2)
C19—O7—C27117.84 (18)C14—C15—C16120.8 (2)
C24—O8—C26117.09 (19)C14—C15—H15119.6
O1—C1—C6124.2 (2)C16—C15—H15119.6
O1—C1—C2115.5 (2)C11—C16—C15119.7 (2)
C6—C1—C2120.3 (2)C11—C16—H16120.2
O3—C2—C3126.0 (2)C15—C16—H16120.2
O3—C2—C1115.0 (2)O5—C17—H17A109.5
C3—C2—C1119.0 (2)O5—C17—H17B109.5
C2—C3—C4120.4 (2)H17A—C17—H17B109.5
C2—C3—H3119.8O5—C17—H17C109.5
C4—C3—H3119.8H17A—C17—H17C109.5
C5—C4—C3119.8 (2)H17B—C17—H17C109.5
C5—C4—C7118.1 (2)O6—C18—C14126.3 (3)
C3—C4—C7122.1 (2)O6—C18—H18116.9
C4—C5—C6120.9 (2)C14—C18—H18116.9
C4—C5—H5119.5O7—C19—C20124.6 (2)
C6—C5—H5119.5O7—C19—C24115.1 (2)
C1—C6—C5119.5 (2)C20—C19—C24120.3 (2)
C1—C6—H6120.3C21—C20—C19119.9 (2)
C5—C6—H6120.3C21—C20—H20120.1
O4—C7—C4125.2 (3)C19—C20—H20120.1
O4—C7—H7117.4C20—C21—C22120.2 (2)
C4—C7—H7117.4C20—C21—H21119.9
O3—C8—H8A109.5C22—C21—H21119.9
O3—C8—H8B109.5C23—C22—C21119.7 (2)
H8A—C8—H8B109.5C23—C22—C25118.6 (2)
O3—C8—H8C109.5C21—C22—C25121.7 (2)
H8A—C8—H8C109.5C24—C23—C22120.7 (2)
H8B—C8—H8C109.5C24—C23—H23119.7
O1—C9—C10105.3 (2)C22—C23—H23119.7
O1—C9—H9A110.7O8—C24—C23124.5 (2)
C10—C9—H9A110.7O8—C24—C19116.3 (2)
O1—C9—H9B110.7C23—C24—C19119.1 (2)
C10—C9—H9B110.7O9—C25—C22125.4 (3)
H9A—C9—H9B108.8O9—C25—H25117.3
O2—C10—C9105.2 (2)C22—C25—H25117.3
O2—C10—H10A110.7O8—C26—H26A109.5
C9—C10—H10A110.7O8—C26—H26B109.5
O2—C10—H10B110.7H26A—C26—H26B109.5
C9—C10—H10B110.7O8—C26—H26C109.5
H10A—C10—H10B108.8H26A—C26—H26C109.5
O2—C11—C16124.5 (2)H26B—C26—H26C109.5
O2—C11—C12115.1 (2)O7—C27—C27i105.2 (2)
C16—C11—C12120.5 (2)O7—C27—H27A110.7
O5—C12—C13125.6 (2)C27i—C27—H27A110.7
O5—C12—C11115.43 (19)O7—C27—H27B110.7
C13—C12—C11119.0 (2)C27i—C27—H27B110.7
C12—C13—C14120.2 (2)H27A—C27—H27B108.8
C12—C13—H13119.9
C9—O1—C1—C60.7 (3)C11—C12—C13—C141.1 (4)
C9—O1—C1—C2179.2 (2)C12—C13—C14—C150.5 (4)
C8—O3—C2—C33.9 (4)C12—C13—C14—C18178.6 (2)
C8—O3—C2—C1174.8 (3)C13—C14—C15—C161.8 (4)
O1—C1—C2—O30.9 (3)C18—C14—C15—C16177.4 (2)
C6—C1—C2—O3179.0 (2)O2—C11—C16—C15179.1 (2)
O1—C1—C2—C3179.7 (2)C12—C11—C16—C150.3 (4)
C6—C1—C2—C30.2 (4)C14—C15—C16—C111.4 (4)
O3—C2—C3—C4179.1 (2)C15—C14—C18—O6178.0 (3)
C1—C2—C3—C40.4 (4)C13—C14—C18—O61.2 (5)
C2—C3—C4—C50.8 (4)C27—O7—C19—C203.8 (3)
C2—C3—C4—C7177.5 (2)C27—O7—C19—C24176.1 (2)
C3—C4—C5—C61.0 (4)O7—C19—C20—C21179.8 (2)
C7—C4—C5—C6177.4 (2)C24—C19—C20—C210.1 (4)
O1—C1—C6—C5179.5 (2)C19—C20—C21—C221.0 (4)
C2—C1—C6—C50.3 (4)C20—C21—C22—C230.1 (4)
C4—C5—C6—C10.7 (4)C20—C21—C22—C25179.6 (2)
C5—C4—C7—O4178.3 (3)C21—C22—C23—C241.8 (4)
C3—C4—C7—O40.0 (4)C25—C22—C23—C24177.7 (2)
C1—O1—C9—C10178.7 (2)C26—O8—C24—C233.1 (4)
C11—O2—C10—C9176.1 (2)C26—O8—C24—C19179.0 (3)
O1—C9—C10—O2179.84 (17)C22—C23—C24—O8179.3 (2)
C10—O2—C11—C164.1 (3)C22—C23—C24—C192.9 (4)
C10—O2—C11—C12177.1 (2)O7—C19—C24—O80.1 (3)
C17—O5—C12—C132.2 (4)C20—C19—C24—O8180.0 (2)
C17—O5—C12—C11177.1 (2)O7—C19—C24—C23177.9 (2)
O2—C11—C12—O51.1 (3)C20—C19—C24—C232.0 (4)
C16—C11—C12—O5177.8 (2)C23—C22—C25—O9167.5 (3)
O2—C11—C12—C13179.6 (2)C21—C22—C25—O912.0 (4)
C16—C11—C12—C131.5 (4)C19—O7—C27—C27i178.3 (2)
O5—C12—C13—C14178.1 (2)
Symmetry code: (i) x+2, y+1, z.
 

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