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The mol­ecule of the title compound, C20H20O6, has a centre of symmetry located at the mid-point of the C=C double bond. The aldehyde C, ­oxy O, meth­oxy O and aldehyde O atoms lie in the benzene ring plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018181/hk2231sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018181/hk2231Isup2.hkl
Contains datablock I

CCDC reference: 647574

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.054
  • wR factor = 0.139
  • Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level B REFLT03_ALERT_3_B Reflection count < 90% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _diffrn_reflns_theta_full 25.00 From the CIF: _reflns_number_total 1368 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1537 Completeness (_total/calc) 89.00% PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low .... 0.89
Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.22
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 1 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Benzaldehyde and its derivatives are the major important compounds to obtain biologically active compounds. The aldehyde (thio)semicarbazones are a class of small molecules that have been evaluated over the last 50 years as antiviral, anticancer (Finch et al., 1999) and antiparasitical (Greenbaum et al., 2004; Wilson et al., 1974; Du et al., 2002; Easmon et al., 2001). Benzaldehyde derivatives are important starting materials for obtaining Schiff bases and oxime-type ligands and their transition metal complexes (Vigato & Tamburini, 2004; Sancak et al., 2007). These types of ligands display a wide variety of structures with different flexibility and electronic nature and the presence of additional donor atoms besides imino nitrogen. Further finetuning of their coordination characteristics can be achieved by varying the nature and positions of the substituents. Some Schiff bases and their complexes have been studied because of catalytic activities in hydrogenation of olefins (Jones et al., 1979) and photochromic properties (Dugas & Pennev, 1981). Many reports have demonstrated the potential of Schiff base or oxime complexes in the construction of polynuclear aromatic compounds (Sengottuvelan et al., 2002).

In the molecule of (I), (Fig. 1), the bond lengths and angles (Table 1) are generally within normal ranges (Allen et al., 1987). It has a centre of symmetry located at the mid-point of the CC double bond. The atoms C7, O1, O2 and O3 lie in the benzene ring plane, while atoms C8, C9 and C10 are 0.134 (3), 0.089 (2) and 0.142 (3) Å away, respectively. The O3C7 bond [1.210 (4) Å] agrees with the corresponding value [1.200 (3) Å] in 2,2'-[2,3-bis(1-formyl-2-naphthyloxymethyl)-but-2-ene-1,4-diyldioxy]bis- (naphthalene-1-carbaldehyde) (Ustabaş et al., 2006).

Related literature top

For general backgroud, see: Allen et al. (1987); Du et al. (2002); Dugas & Penney, 1981; Easmon et al. (2001); Finch et al. (1999); Greenbaum et al. (2004); Jones et al. (1979); Sancak et al. (2007); Sengottuvelan et al. (2002); Vigato & Tamburini (2004); Wilson et al. (1974). For a related structure see: Ustabaş et al. (2006). For structure analysis tools used, see: Bruker (1997); Farrugia (1997); Farrugia (1999); Sheldrick (1997).

Experimental top

For the preparation of the title compound, the corresponding 4-hydroxy-3-methoxy benzaldehyde (3.04 g, 10 mmol) was refluxed with potassium hydroxide (1.121 g, 10 mmol) in absolute ethanol (100 ml) for 1 h. Then, trans 1,4-dichloro2-butene (2.138 g, 40 mmol) was added and refluxed for an additional 26 h. The precipitate was filtered off, washed with water and recrystallized from chloroform/acetone (1:1) (yield; 2.145 g, 60%, m.p. 444–445 K).

Refinement top

H10 was located in difference syntheses and refined isotropically [C—H = 0.90 (3) Å and Uiso(H) = 0.056 (9) Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Structure description top

Benzaldehyde and its derivatives are the major important compounds to obtain biologically active compounds. The aldehyde (thio)semicarbazones are a class of small molecules that have been evaluated over the last 50 years as antiviral, anticancer (Finch et al., 1999) and antiparasitical (Greenbaum et al., 2004; Wilson et al., 1974; Du et al., 2002; Easmon et al., 2001). Benzaldehyde derivatives are important starting materials for obtaining Schiff bases and oxime-type ligands and their transition metal complexes (Vigato & Tamburini, 2004; Sancak et al., 2007). These types of ligands display a wide variety of structures with different flexibility and electronic nature and the presence of additional donor atoms besides imino nitrogen. Further finetuning of their coordination characteristics can be achieved by varying the nature and positions of the substituents. Some Schiff bases and their complexes have been studied because of catalytic activities in hydrogenation of olefins (Jones et al., 1979) and photochromic properties (Dugas & Pennev, 1981). Many reports have demonstrated the potential of Schiff base or oxime complexes in the construction of polynuclear aromatic compounds (Sengottuvelan et al., 2002).

In the molecule of (I), (Fig. 1), the bond lengths and angles (Table 1) are generally within normal ranges (Allen et al., 1987). It has a centre of symmetry located at the mid-point of the CC double bond. The atoms C7, O1, O2 and O3 lie in the benzene ring plane, while atoms C8, C9 and C10 are 0.134 (3), 0.089 (2) and 0.142 (3) Å away, respectively. The O3C7 bond [1.210 (4) Å] agrees with the corresponding value [1.200 (3) Å] in 2,2'-[2,3-bis(1-formyl-2-naphthyloxymethyl)-but-2-ene-1,4-diyldioxy]bis- (naphthalene-1-carbaldehyde) (Ustabaş et al., 2006).

For general backgroud, see: Allen et al. (1987); Du et al. (2002); Dugas & Penney, 1981; Easmon et al. (2001); Finch et al. (1999); Greenbaum et al. (2004); Jones et al. (1979); Sancak et al. (2007); Sengottuvelan et al. (2002); Vigato & Tamburini (2004); Wilson et al. (1974). For a related structure see: Ustabaş et al. (2006). For structure analysis tools used, see: Bruker (1997); Farrugia (1997); Farrugia (1999); Sheldrick (1997).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Primed atoms are related to the unprimed atoms by the symmetry operator: 2 - x, 2 - y, 2 - z.
(E)-4,4'-(But-2-ene-1,4-diyldioxy)bis(3-methoxybenzaldehyde) top
Crystal data top
C20H20O6F(000) = 376
Mr = 356.36Dx = 1.359 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 836 reflections
a = 4.0639 (9) Åθ = 2.0–25.0°
b = 15.617 (3) ŵ = 0.10 mm1
c = 13.735 (3) ÅT = 294 K
β = 92.212 (4)°Prism, colorless
V = 871.0 (3) Å30.42 × 0.19 × 0.16 mm
Z = 2
Data collection top
Bruker CCD area-detector
diffractometer
836 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
φ and ω scansh = 44
3568 measured reflectionsk = 1813
1368 independent reflectionsl = 1613
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0692P)2]
where P = (Fo2 + 2Fc2)/3
1368 reflections(Δ/σ)max < 0.001
122 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C20H20O6V = 871.0 (3) Å3
Mr = 356.36Z = 2
Monoclinic, P21/nMo Kα radiation
a = 4.0639 (9) ŵ = 0.10 mm1
b = 15.617 (3) ÅT = 294 K
c = 13.735 (3) Å0.42 × 0.19 × 0.16 mm
β = 92.212 (4)°
Data collection top
Bruker CCD area-detector
diffractometer
836 reflections with I > 2σ(I)
3568 measured reflectionsRint = 0.046
1368 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.16 e Å3
1368 reflectionsΔρmin = 0.18 e Å3
122 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
O11.2583 (5)0.83308 (11)0.95737 (14)0.0456 (6)
O21.4321 (5)0.69144 (11)1.03941 (14)0.0528 (6)
O31.9445 (7)0.51354 (15)0.76387 (18)0.0788 (9)
C11.3981 (7)0.77503 (15)0.8979 (2)0.0368 (7)
C21.4979 (7)0.69800 (15)0.9429 (2)0.0382 (7)
C31.6459 (7)0.63623 (16)0.8898 (2)0.0432 (8)
H31.71290.58530.91970.052*
C41.6976 (7)0.64900 (16)0.7908 (2)0.0418 (8)
C51.6001 (8)0.72447 (18)0.7472 (2)0.0490 (8)
H51.63360.73300.68130.059*
C61.4525 (7)0.78787 (17)0.8007 (2)0.0447 (8)
H61.39010.83920.77100.054*
C71.8599 (8)0.5833 (2)0.7339 (3)0.0585 (10)
H71.90160.59630.66950.070*
C81.5004 (10)0.61245 (19)1.0854 (3)0.0714 (12)
H8A1.44260.61561.15240.107*
H8B1.73090.59981.08190.107*
H8C1.37430.56811.05310.107*
C91.1295 (8)0.91024 (15)0.9134 (2)0.0440 (8)
H9A0.97000.89650.86140.053*
H9B1.30590.94340.88620.053*
C100.9710 (7)0.95961 (17)0.9906 (2)0.0401 (8)
H100.830 (7)0.9284 (18)1.025 (2)0.056 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0663 (15)0.0312 (11)0.0405 (14)0.0094 (9)0.0170 (10)0.0012 (9)
O20.0896 (16)0.0399 (11)0.0303 (13)0.0138 (11)0.0198 (11)0.0025 (9)
O30.102 (2)0.0513 (15)0.085 (2)0.0161 (14)0.0317 (17)0.0153 (13)
C10.0444 (18)0.0317 (15)0.0352 (19)0.0031 (12)0.0125 (14)0.0046 (12)
C20.0543 (19)0.0326 (15)0.0283 (18)0.0017 (13)0.0102 (14)0.0015 (12)
C30.059 (2)0.0293 (15)0.042 (2)0.0005 (13)0.0147 (15)0.0020 (13)
C40.051 (2)0.0380 (17)0.0371 (19)0.0078 (13)0.0144 (15)0.0104 (13)
C50.065 (2)0.0490 (19)0.0344 (19)0.0097 (15)0.0164 (16)0.0047 (14)
C60.061 (2)0.0362 (16)0.0373 (19)0.0002 (14)0.0138 (15)0.0028 (13)
C70.074 (2)0.052 (2)0.051 (2)0.0059 (18)0.0274 (19)0.0176 (16)
C80.120 (3)0.055 (2)0.041 (2)0.023 (2)0.016 (2)0.0109 (17)
C90.0533 (19)0.0331 (15)0.046 (2)0.0032 (13)0.0079 (15)0.0017 (13)
C100.0435 (19)0.0335 (14)0.044 (2)0.0011 (14)0.0118 (15)0.0035 (14)
Geometric parameters (Å, º) top
O1—C11.359 (3)C5—H50.9300
O1—C91.438 (3)C6—C51.383 (4)
O2—C21.366 (3)C6—H60.9300
O2—C81.408 (3)C7—H70.9300
O3—C71.210 (4)C8—H8A0.9600
C1—C61.376 (4)C8—H8B0.9600
C1—C21.405 (3)C8—H8C0.9600
C2—C31.363 (4)C9—H9A0.9700
C3—C41.398 (4)C9—H9B0.9700
C3—H30.9300C10—C10i1.307 (5)
C4—C71.462 (4)C10—C91.479 (4)
C5—C41.373 (4)C10—H100.90 (3)
C1—O1—C9117.4 (2)C5—C6—H6120.0
C2—O2—C8117.3 (2)O3—C7—C4125.3 (3)
O1—C1—C6124.9 (2)O3—C7—H7117.3
O1—C1—C2115.3 (2)C4—C7—H7117.3
C6—C1—C2119.8 (2)O2—C8—H8A109.5
C3—C2—O2124.9 (2)O2—C8—H8B109.5
C3—C2—C1119.8 (3)H8A—C8—H8B109.5
O2—C2—C1115.3 (2)O2—C8—H8C109.5
C2—C3—C4120.3 (3)H8A—C8—H8C109.5
C2—C3—H3119.8H8B—C8—H8C109.5
C4—C3—H3119.8O1—C9—C10107.3 (2)
C5—C4—C3119.7 (3)O1—C9—H9A110.3
C5—C4—C7119.8 (3)C10—C9—H9A110.3
C3—C4—C7120.5 (3)O1—C9—H9B110.3
C4—C5—C6120.4 (3)C10—C9—H9B110.3
C4—C5—H5119.8H9A—C9—H9B108.5
C6—C5—H5119.8C10i—C10—C9124.4 (4)
C1—C6—C5120.0 (3)C10i—C10—H10122 (2)
C1—C6—H6120.0C9—C10—H10113.5 (19)
C9—O1—C1—C66.3 (4)O2—C2—C3—C4179.1 (3)
C9—O1—C1—C2175.4 (2)C1—C2—C3—C40.3 (5)
C1—O1—C9—C10176.0 (2)C2—C3—C4—C50.4 (5)
C8—O2—C2—C35.0 (4)C2—C3—C4—C7179.2 (3)
C8—O2—C2—C1174.4 (3)C5—C4—C7—O3177.1 (3)
O1—C1—C2—C3178.9 (3)C3—C4—C7—O34.1 (5)
C6—C1—C2—C30.5 (4)C6—C5—C4—C30.2 (5)
O1—C1—C2—O21.7 (4)C6—C5—C4—C7178.6 (3)
C6—C1—C2—O2179.9 (3)C1—C6—C5—C41.0 (5)
O1—C1—C6—C5179.3 (3)C10i—C10—C9—O1129.2 (4)
C2—C1—C6—C51.1 (4)
Symmetry code: (i) x+2, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC20H20O6
Mr356.36
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)4.0639 (9), 15.617 (3), 13.735 (3)
β (°) 92.212 (4)
V3)871.0 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.42 × 0.19 × 0.16
Data collection
DiffractometerBruker CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3568, 1368, 836
Rint0.046
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.139, 1.04
No. of reflections1368
No. of parameters122
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.18

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
O1—C11.359 (3)O2—C81.408 (3)
O1—C91.438 (3)O3—C71.210 (4)
O2—C21.366 (3)
C3—C2—O2124.9 (2)O2—C2—C1115.3 (2)
C3—C2—C1119.8 (3)
 

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