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In the centrosymmetric title compound, C28H26O6, the dihedral angle between the central and terminal aromatic rings is 27.72 (9)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026281/tk2159sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026281/tk2159Isup2.hkl
Contains datablock I

CCDC reference: 654856

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.042
  • wR factor = 0.117
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 90 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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

As part of our ongoing studies of organic nonlinear optical materials derived from chalcone (Harrison et al., 2007a,b), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

The molecule of (I) is centrosymmetric and the dihedral angle between the central C1—C3/C1i—C3i (i = -x, 1 - y, 2 - z) and pendant C7—C12 benzene rings is 27.72 (9)°. The dihedral angles for the enone (C4/C5/C6/O1) fragment with respect to C1—C3/C1i—C3i and C7—C12 are 15.54 (12)° and 12.93 (12)°, respectively. The terminal C14 methyl carbon atom is displaced slightly further from the C7—C12 ring than is C13 [deviations = -0.073 (3) Å and 0.151 (3) Å, respectively].

There are no π-π stacking interactions in (I) and the crystal packing (Fig. 2), which bears little if any resemblence to that in the related compound (2E,2'E)-3,3'-(1,4-phenylene)bis[1-(4-methoxyphenyl)prop-2-en-1-one] (Harrison et al., 2007a), appears to be controlled by van der Waals forces.

Related literature top

For a related structure, see: Harrison et al. (2007a). For background, see: Harrison et al. (2007b).

Experimental top

A solution of ethanol (25 ml) and 10% sodium hydroxide (5 ml) solution were taken in a conical flask. A previously prepared small portion of terephthalaldehyde (0.001 mol) and 1-(3,4-dimethoxyphenyl)ethanone (0.002 mol) dissolved in methanol was added to the conical flask with stirring and the temperature of the solution was maintained between 298–303 K. A precipitate was obtained after stirring the solution for about five minutes. The remaining portion of the aldehyde and ketone mixture was added and the solution was stirred for a further 30 minutes. The separated product was filtered and washed with water and dried. The crude product was recrystallized from DMF solution and single crystals of (I) were grown by slow evaporation of a second DMF solution.

Refinement top

The hydrogen atoms were placed in calculated positions (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate but not to tip to best fit the electron density.

Structure description top

As part of our ongoing studies of organic nonlinear optical materials derived from chalcone (Harrison et al., 2007a,b), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

The molecule of (I) is centrosymmetric and the dihedral angle between the central C1—C3/C1i—C3i (i = -x, 1 - y, 2 - z) and pendant C7—C12 benzene rings is 27.72 (9)°. The dihedral angles for the enone (C4/C5/C6/O1) fragment with respect to C1—C3/C1i—C3i and C7—C12 are 15.54 (12)° and 12.93 (12)°, respectively. The terminal C14 methyl carbon atom is displaced slightly further from the C7—C12 ring than is C13 [deviations = -0.073 (3) Å and 0.151 (3) Å, respectively].

There are no π-π stacking interactions in (I) and the crystal packing (Fig. 2), which bears little if any resemblence to that in the related compound (2E,2'E)-3,3'-(1,4-phenylene)bis[1-(4-methoxyphenyl)prop-2-en-1-one] (Harrison et al., 2007a), appears to be controlled by van der Waals forces.

For a related structure, see: Harrison et al. (2007a). For background, see: Harrison et al. (2007b).

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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) showing 30% displacement ellipsoids (H atoms are drawn as spheres of arbitrary radius). Symmetry code: (i) -x, 1 - y, 2 - z.
[Figure 2] Fig. 2. Unit cell packing for (I) with hydrogen atoms omitted for clarity.
(2E,2'E)-3,3'-(1,4-Phenylene)bis[1-(3,4-methoxyphenyl)prop-2-en-1-one] top
Crystal data top
C28H26O6F(000) = 484
Mr = 458.48Dx = 1.328 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2493 reflections
a = 10.6974 (9) Åθ = 4.4–27.3°
b = 10.4056 (9) ŵ = 0.09 mm1
c = 11.0337 (9) ÅT = 295 K
β = 111.015 (2)°Slab, pale yellow
V = 1146.50 (17) Å30.51 × 0.47 × 0.28 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1845 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 27.6°, θmin = 4.5°
ω scansh = 1213
6150 measured reflectionsk = 137
2593 independent reflectionsl = 1413
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0581P)2 + 0.102P]
where P = (Fo2 + 2Fc2)/3
2593 reflections(Δ/σ)max = 0.001
156 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C28H26O6V = 1146.50 (17) Å3
Mr = 458.48Z = 2
Monoclinic, P21/nMo Kα radiation
a = 10.6974 (9) ŵ = 0.09 mm1
b = 10.4056 (9) ÅT = 295 K
c = 11.0337 (9) Å0.51 × 0.47 × 0.28 mm
β = 111.015 (2)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1845 reflections with I > 2σ(I)
6150 measured reflectionsRint = 0.037
2593 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.03Δρmax = 0.14 e Å3
2593 reflectionsΔρmin = 0.23 e Å3
156 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
C10.02570 (14)0.62724 (13)0.98401 (14)0.0531 (4)
H10.04260.71340.97350.064*
C20.06430 (13)0.53394 (12)0.91311 (12)0.0458 (3)
C30.03669 (14)0.40569 (13)0.93106 (14)0.0543 (4)
H30.06080.34160.88490.065*
C40.13242 (13)0.57377 (13)0.82596 (13)0.0492 (3)
H40.15270.66080.82690.059*
C50.16902 (14)0.50108 (13)0.74548 (14)0.0520 (3)
H50.15100.41340.74090.062*
C60.23769 (14)0.55662 (13)0.66305 (14)0.0522 (3)
C70.24029 (13)0.48429 (12)0.54784 (13)0.0480 (3)
C80.16721 (13)0.37084 (12)0.50367 (13)0.0488 (3)
H80.11490.33800.54790.059*
C90.17175 (13)0.30731 (13)0.39578 (13)0.0480 (3)
C100.25223 (13)0.35637 (14)0.32880 (13)0.0497 (3)
C110.32134 (15)0.46974 (14)0.37027 (15)0.0567 (4)
H110.37200.50410.32500.068*
C120.31592 (15)0.53259 (14)0.47846 (15)0.0561 (4)
H120.36360.60850.50550.067*
C130.01953 (17)0.14495 (16)0.40800 (18)0.0678 (4)
H13A0.02190.06760.36450.102*
H13B0.04840.20670.40430.102*
H13C0.07160.12600.49700.102*
C140.34061 (18)0.32855 (19)0.16052 (17)0.0758 (5)
H14A0.33660.26900.09270.114*
H14B0.43120.33460.22070.114*
H14C0.31090.41160.12350.114*
O10.29246 (12)0.66240 (10)0.68998 (12)0.0766 (4)
O20.10457 (11)0.19627 (10)0.34583 (11)0.0651 (3)
O30.25563 (10)0.28434 (11)0.22740 (10)0.0629 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0634 (9)0.0385 (7)0.0622 (8)0.0027 (6)0.0285 (7)0.0062 (6)
C20.0445 (7)0.0438 (7)0.0477 (7)0.0000 (5)0.0148 (6)0.0045 (5)
C30.0655 (9)0.0433 (7)0.0609 (8)0.0002 (6)0.0311 (7)0.0108 (6)
C40.0506 (7)0.0428 (7)0.0547 (8)0.0004 (6)0.0196 (6)0.0022 (6)
C50.0585 (8)0.0417 (7)0.0610 (8)0.0018 (6)0.0278 (7)0.0023 (6)
C60.0536 (8)0.0422 (7)0.0668 (9)0.0002 (6)0.0287 (7)0.0003 (6)
C70.0497 (7)0.0412 (7)0.0576 (8)0.0022 (6)0.0249 (6)0.0044 (6)
C80.0500 (7)0.0453 (7)0.0586 (8)0.0011 (6)0.0286 (6)0.0045 (6)
C90.0450 (7)0.0449 (7)0.0568 (8)0.0017 (5)0.0216 (6)0.0023 (6)
C100.0490 (7)0.0548 (8)0.0480 (7)0.0026 (6)0.0205 (6)0.0052 (6)
C110.0615 (8)0.0566 (8)0.0624 (9)0.0058 (7)0.0347 (7)0.0075 (7)
C120.0610 (8)0.0455 (7)0.0683 (9)0.0090 (6)0.0312 (7)0.0016 (7)
C130.0689 (10)0.0598 (9)0.0853 (11)0.0209 (8)0.0404 (9)0.0075 (8)
C140.0750 (11)0.1011 (14)0.0658 (10)0.0157 (10)0.0426 (9)0.0087 (9)
O10.0974 (9)0.0538 (7)0.1000 (9)0.0231 (6)0.0612 (7)0.0188 (6)
O20.0719 (7)0.0612 (6)0.0760 (7)0.0203 (5)0.0433 (6)0.0156 (5)
O30.0667 (6)0.0735 (7)0.0580 (6)0.0107 (5)0.0339 (5)0.0067 (5)
Geometric parameters (Å, º) top
C1—C3i1.3746 (19)C8—H80.9300
C1—C21.3988 (18)C9—O21.3679 (16)
C1—H10.9300C9—C101.4157 (18)
C2—C31.3962 (19)C10—O31.3580 (16)
C2—C41.4594 (18)C10—C111.380 (2)
C3—C1i1.3746 (19)C11—C121.380 (2)
C3—H30.9300C11—H110.9300
C4—C51.3279 (18)C12—H120.9300
C4—H40.9300C13—O21.4250 (17)
C5—C61.4765 (18)C13—H13A0.9600
C5—H50.9300C13—H13B0.9600
C6—O11.2322 (17)C13—H13C0.9600
C6—C71.4861 (19)C14—O31.4366 (18)
C7—C121.3918 (18)C14—H14A0.9600
C7—C81.4033 (18)C14—H14B0.9600
C8—C91.3777 (19)C14—H14C0.9600
C3i—C1—C2121.41 (13)O2—C9—C10115.10 (12)
C3i—C1—H1119.3C8—C9—C10119.64 (12)
C2—C1—H1119.3O3—C10—C11125.13 (12)
C3—C2—C1117.65 (12)O3—C10—C9115.60 (12)
C3—C2—C4123.09 (12)C11—C10—C9119.26 (13)
C1—C2—C4119.25 (12)C10—C11—C12120.53 (12)
C1i—C3—C2120.94 (12)C10—C11—H11119.7
C1i—C3—H3119.5C12—C11—H11119.7
C2—C3—H3119.5C11—C12—C7121.16 (13)
C5—C4—C2127.99 (13)C11—C12—H12119.4
C5—C4—H4116.0C7—C12—H12119.4
C2—C4—H4116.0O2—C13—H13A109.5
C4—C5—C6121.34 (12)O2—C13—H13B109.5
C4—C5—H5119.3H13A—C13—H13B109.5
C6—C5—H5119.3O2—C13—H13C109.5
O1—C6—C5119.98 (13)H13A—C13—H13C109.5
O1—C6—C7120.36 (12)H13B—C13—H13C109.5
C5—C6—C7119.65 (12)O3—C14—H14A109.5
C12—C7—C8118.30 (13)O3—C14—H14B109.5
C12—C7—C6118.72 (12)H14A—C14—H14B109.5
C8—C7—C6122.96 (12)O3—C14—H14C109.5
C9—C8—C7121.06 (12)H14A—C14—H14C109.5
C9—C8—H8119.5H14B—C14—H14C109.5
C7—C8—H8119.5C9—O2—C13117.16 (11)
O2—C9—C8125.26 (12)C10—O3—C14117.09 (12)
C3i—C1—C2—C30.3 (2)C7—C8—C9—O2179.78 (12)
C3i—C1—C2—C4178.89 (12)C7—C8—C9—C100.5 (2)
C1—C2—C3—C1i0.3 (2)O2—C9—C10—O32.31 (18)
C4—C2—C3—C1i178.86 (13)C8—C9—C10—O3177.00 (12)
C3—C2—C4—C55.4 (2)O2—C9—C10—C11178.49 (12)
C1—C2—C4—C5175.49 (14)C8—C9—C10—C112.2 (2)
C2—C4—C5—C6179.98 (13)O3—C10—C11—C12176.94 (13)
C4—C5—C6—O118.6 (2)C9—C10—C11—C122.2 (2)
C4—C5—C6—C7161.43 (13)C10—C11—C12—C70.5 (2)
O1—C6—C7—C125.9 (2)C8—C7—C12—C111.2 (2)
C5—C6—C7—C12174.11 (13)C6—C7—C12—C11179.64 (13)
O1—C6—C7—C8172.50 (14)C8—C9—O2—C132.3 (2)
C5—C6—C7—C87.5 (2)C10—C9—O2—C13178.43 (13)
C12—C7—C8—C91.1 (2)C11—C10—O3—C141.6 (2)
C6—C7—C8—C9179.53 (12)C9—C10—O3—C14177.53 (13)
Symmetry code: (i) x, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC28H26O6
Mr458.48
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)10.6974 (9), 10.4056 (9), 11.0337 (9)
β (°) 111.015 (2)
V3)1146.50 (17)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.51 × 0.47 × 0.28
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6150, 2593, 1845
Rint0.037
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.117, 1.03
No. of reflections2593
No. of parameters156
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.23

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

 

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