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The title compound, C20H22O6, was prepared by the reaction of 4-hydr­oxy-3-methoxy­benzaldehyde and 1,4-dibromo­butane. A crystallographic center of symmetry is located at the mid-point of the central C-C bond. The four C atoms linking the two aromatic rings are coplanar and the two aromatic rings are parallel to each other.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502951X/wn6378sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680502951X/wn6378Isup2.hkl
Contains datablock I

CCDC reference: 287747

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.036
  • wR factor = 0.101
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Comment top

Crystal engineering plays an important role in the preparation of crystalline solid materials, enabling their architecture and properties to be predictable (Parashar et al., 1988; Tynan et al., 2005). We are interested in the molecular and ionic recognition of crown ethers. As part of this study, we report the synthesis and structure of the title compound, (I), which will provide useful information on its physical and chemical properties.

A view of the molecule is shown in Fig. 1. A crystallographic center of symmetry is located at the mid-point of the C10—C10i bond [symmetry code: (i) −x, −y, 2 − z]. The vanillin moiety (C1–C8/O1–O3) is planar, with an r.m.s. deviation for fitted atoms of 0.0289 Å. The chain of atoms C9—C10—C10i—C9i linking the two vanillin systems is planar and this plane makes a dihedral angle of 5.2 (2)° with the vanillin plane. The two aromatic rings in the molecule are parallel to each other. The bond lengths and angles are unexceptional.

Experimental top

To a solution of 4-hydroxy-3-methoxybenzaldehyde (15.2 g, 10 mmol) and potassium carbonate (13.8 g, 10 mmol) in acetonitrile (500 ml), 1,4-dibromobutane (10.8 g, 5 mmol) was added over a period of 30 min and the mixture refluxed for 24 h under nitrogen. The solvent was removed and the resultant oil poured into ice–water (500 ml). The white precipitate was then isolated and recrystallized from ethanol to give the pure compound in 63% yield. Colorless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.

Refinement top

H atoms were included in calculated positions and refined using a riding-model approximation; C—H = 0.93 (aromatic), 0.96 (methyl) and 0.97 Å (methylene), and Uiso(H) = xUeq(C), where x = 1.5 for methyl and 1.2 for other H atoms.

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.

Figures top
[Figure 1] Fig. 1. The structure of (I), with displacement ellipsoids for non-H atoms drawn at the 30% probability level. [Symmetry code: (i) −x, −y, 2 − z.]
4-[4-(4-Formyl-2-methoxyphenoxy)butoxy]-3-methoxybenzaldehyde top
Crystal data top
C20H22O6F(000) = 380
Mr = 358.38Dx = 1.282 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybcCell parameters from 1740 reflections
a = 7.4200 (16) Åθ = 2.8–26.3°
b = 7.6630 (16) ŵ = 0.10 mm1
c = 16.407 (3) ÅT = 294 K
β = 95.787 (4)°Block, colorless
V = 928.2 (3) Å30.36 × 0.30 × 0.24 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1632 independent reflections
Radiation source: fine-focus sealed tube1142 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 87
Tmin = 0.944, Tmax = 0.977k = 98
4527 measured reflectionsl = 1419
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0429P)2 + 0.2073P]
where P = (Fo2 + 2Fc2)/3
1632 reflections(Δ/σ)max = 0.001
119 parametersΔρmax = 0.14 e Å3
6 restraintsΔρmin = 0.14 e Å3
Crystal data top
C20H22O6V = 928.2 (3) Å3
Mr = 358.38Z = 2
Monoclinic, P21/cMo Kα radiation
a = 7.4200 (16) ŵ = 0.10 mm1
b = 7.6630 (16) ÅT = 294 K
c = 16.407 (3) Å0.36 × 0.30 × 0.24 mm
β = 95.787 (4)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1632 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
1142 reflections with I > 2σ(I)
Tmin = 0.944, Tmax = 0.977Rint = 0.028
4527 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0366 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.04Δρmax = 0.14 e Å3
1632 reflectionsΔρmin = 0.14 e Å3
119 parameters
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 > 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
O10.34776 (14)0.12609 (14)0.93658 (7)0.0478 (3)
O20.58088 (16)0.37044 (15)0.93058 (8)0.0561 (4)
O30.9952 (2)0.1593 (2)0.70978 (12)0.1046 (6)
C10.4770 (2)0.0965 (2)0.88525 (9)0.0394 (4)
C20.4892 (2)0.0514 (2)0.83826 (10)0.0502 (5)
H20.40700.14210.84160.060*
C30.6242 (2)0.0645 (2)0.78607 (11)0.0529 (5)
H30.63230.16470.75470.063*
C40.7463 (2)0.0687 (2)0.78007 (10)0.0463 (4)
C50.7368 (2)0.2177 (2)0.82858 (10)0.0440 (4)
H50.82010.30740.82520.053*
C60.6049 (2)0.2321 (2)0.88113 (9)0.0389 (4)
C70.7032 (3)0.5134 (2)0.92870 (14)0.0750 (7)
H7A0.82440.47390.94460.112*
H7B0.67150.60210.96600.112*
H7C0.69610.56040.87420.112*
C80.8809 (3)0.0528 (3)0.72112 (13)0.0650 (6)
H80.87780.04830.68970.078*
C90.2067 (2)0.0015 (2)0.93851 (10)0.0452 (4)
H9A0.25740.11290.95730.054*
H9B0.14410.01710.88420.054*
C100.0776 (2)0.0643 (2)0.99644 (10)0.0446 (4)
H10A0.02840.17580.97710.054*
H10B0.14260.08221.05010.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0405 (6)0.0500 (7)0.0558 (7)0.0139 (5)0.0190 (5)0.0081 (6)
O20.0567 (8)0.0428 (7)0.0740 (9)0.0145 (6)0.0326 (6)0.0130 (6)
O30.0961 (12)0.1047 (13)0.1261 (15)0.0170 (11)0.0760 (11)0.0200 (11)
C10.0348 (9)0.0451 (9)0.0387 (8)0.0023 (7)0.0059 (7)0.0001 (7)
C20.0454 (10)0.0517 (11)0.0542 (10)0.0114 (8)0.0085 (8)0.0097 (9)
C30.0504 (10)0.0572 (11)0.0511 (10)0.0007 (9)0.0051 (8)0.0161 (9)
C40.0404 (10)0.0551 (11)0.0444 (9)0.0059 (8)0.0086 (7)0.0004 (8)
C50.0381 (9)0.0454 (10)0.0499 (10)0.0017 (7)0.0119 (7)0.0049 (8)
C60.0375 (8)0.0380 (9)0.0425 (9)0.0004 (7)0.0096 (7)0.0004 (7)
C70.0745 (15)0.0467 (11)0.1113 (18)0.0223 (10)0.0469 (13)0.0203 (11)
C80.0601 (13)0.0738 (14)0.0649 (13)0.0110 (11)0.0245 (10)0.0058 (11)
C90.0369 (9)0.0501 (10)0.0491 (10)0.0144 (8)0.0069 (7)0.0000 (8)
C100.0368 (9)0.0478 (10)0.0497 (10)0.0083 (8)0.0063 (7)0.0027 (8)
Geometric parameters (Å, º) top
O1—C11.3578 (18)C5—C61.372 (2)
O1—C91.4353 (18)C5—H50.9300
O2—C61.3575 (18)C7—H7A0.9600
O2—C71.425 (2)C7—H7B0.9600
O3—C81.205 (2)C7—H7C0.9600
C1—C21.379 (2)C8—H80.9300
C1—C61.414 (2)C9—C101.503 (2)
C2—C31.386 (2)C9—H9A0.9700
C2—H20.9300C9—H9B0.9700
C3—C41.375 (2)C10—C10i1.529 (3)
C3—H30.9300C10—H10A0.9700
C4—C51.397 (2)C10—H10B0.9700
C4—C81.463 (2)
C1—O1—C9117.53 (12)O2—C7—H7B109.5
C6—O2—C7117.70 (13)H7A—C7—H7B109.5
O1—C1—C2125.06 (14)O2—C7—H7C109.5
O1—C1—C6115.24 (14)H7A—C7—H7C109.5
C2—C1—C6119.70 (15)H7B—C7—H7C109.5
C1—C2—C3119.82 (16)O3—C8—C4125.7 (2)
C1—C2—H2120.1O3—C8—H8117.2
C3—C2—H2120.1C4—C8—H8117.2
C4—C3—C2120.89 (16)O1—C9—C10107.33 (13)
C4—C3—H3119.6O1—C9—H9A110.2
C2—C3—H3119.6C10—C9—H9A110.2
C3—C4—C5119.59 (15)O1—C9—H9B110.2
C3—C4—C8118.92 (17)C10—C9—H9B110.2
C5—C4—C8121.46 (17)H9A—C9—H9B108.5
C6—C5—C4120.29 (15)C9—C10—C10i111.39 (17)
C6—C5—H5119.9C9—C10—H10A109.4
C4—C5—H5119.9C10i—C10—H10A109.4
O2—C6—C5125.71 (14)C9—C10—H10B109.4
O2—C6—C1114.59 (13)C10i—C10—H10B109.4
C5—C6—C1119.69 (15)H10A—C10—H10B108.0
O2—C7—H7A109.5
C9—O1—C1—C23.9 (2)C4—C5—C6—O2179.35 (15)
C9—O1—C1—C6175.47 (14)C4—C5—C6—C10.8 (2)
O1—C1—C2—C3177.96 (16)O1—C1—C6—O21.2 (2)
C6—C1—C2—C31.4 (2)C2—C1—C6—O2179.37 (14)
C1—C2—C3—C40.3 (3)O1—C1—C6—C5177.45 (14)
C2—C3—C4—C51.4 (3)C2—C1—C6—C52.0 (2)
C2—C3—C4—C8176.95 (17)C3—C4—C8—O3179.9 (2)
C3—C4—C5—C60.8 (2)C5—C4—C8—O31.7 (3)
C8—C4—C5—C6177.51 (16)C1—O1—C9—C10177.51 (13)
C7—O2—C6—C50.5 (2)O1—C9—C10—C10i179.36 (16)
C7—O2—C6—C1179.06 (16)
Symmetry code: (i) x, y, z+2.

Experimental details

Crystal data
Chemical formulaC20H22O6
Mr358.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)7.4200 (16), 7.6630 (16), 16.407 (3)
β (°) 95.787 (4)
V3)928.2 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.36 × 0.30 × 0.24
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.944, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
4527, 1632, 1142
Rint0.028
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.101, 1.04
No. of reflections1632
No. of parameters119
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.14

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

 

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