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Acta Cryst. (2009). E65, o538    [ doi:10.1107/S1600536809005005 ]

Bis[4-(2-benzylidenepropylideneamino)phenyl] ether

M. Movahedi, H. Hadadzadeh, K. Fejfarova, M. Dusek and A. Dehno Khalaji

Abstract top

The title compound, C32H28N2O, is a flexible Schiff base displaying a trans configuration across the C=N double bond. It was prepared in high yield by condensation of [alpha]-methylcinnamaldehyde and bis(4-aminophenyl) ether in methanol at room temperature. The sample, with pseudo-orthorhombic cell parameters, exhibited merohedral twinning by rotation 180° around a*, with a refined twin domain fraction of 0.722 (1). The elongated shape of the elementary cell corresponds to the shape and direction of the molecules. The dihedral angle between the O-linked aromatic rings is 57.86 (8)°.

Comment top

Flexible Schiff-base ligands have received a lot of attention in the field of supramolecular coordination chemistry (Laye, 2007; Huang et al., 2005; Chu & Huang, 2007). Because of easy syntheses of these compounds by condensation between aldehydes (or ketones) and amines, many of them were designed and sued to prepare transition metal complexes in recent years. Here, we report the synthesis and crystal structure of a new flexible Schiff-base compound (I). The molecule of (I) is shown in Fig. 1. Bond lengths and angles are comparable with those observed in similar compounds (Hu et al., 2008; Xu et al., 2008). The C(7)=N(1) and C(23)=N(2) bond lengths of 1.266 (3) and 1.270 (3) Å, respectively, conform to the usual value for a C=N double bond. Each half of the molecule displays a trans configuration across the C=N double bond. The prolongated shape of the molecule is reflected by very long b axis about 55 Å. The molecules are isolated (Fig. 2), with no intermolecular contacts. From crystallographic point of view merohedric twinning by rotation 180° around a* and pseudo-orthorhombic cell parameters should be noted. The twinning has occurred regularly in all tested samples.

Related literature top

For the synthesis of the title compound, see: Khalaji & Ng (2008). For related structures, see: Hu et al. (2008); Xu et al. (2008). For background to transition metal complexes, see: Laye (2007); Huang et al. (2005); Chu & Huang (2007).

Experimental top

The title compound was synthesized using a method analogous to the literature procedure of Khalaji and Ng (2008). Crystals appropriate for data collection were obtained by slow evaporation from a methanol-chloroform mixture (1:5 v/v) at room temperature (yield; 88%).

Refinement top

All H atoms were found in difference Fourier maps, but they were constrained to ideal positions. The isotropic atomic displacement parameters of hydrogen atoms were set to 1.2Ueq of the parent atom. The sample had a pseudo-orthorhombic cell parameters and exhibited a merohedric twinning by rotation 180° around a* (with twinning matrix 1 0 0 / 0 - 1 0 / 0 0 - 1 applied to indices expressed like row vectors). The volume fraction of the second domain was refined to 0.278 (1).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2008).

Figures top
[Figure 1] Fig. 1. The molecule of (I) viewed along a with atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The packing of (I) viewed along c.
Bis[4-(2-benzylidenepropylideneamino)phenyl] ether top
Crystal data top
C32H28N2OF(000) = 968
Mr = 456.6Dx = 1.203 Mg m−3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ynCell parameters from 9034 reflections
a = 7.4737 (3) Åθ = 3.2–61.2°
b = 55.929 (3) ŵ = 0.56 mm−1
c = 6.0275 (3) ÅT = 295 K
β = 90.022 (4)°Plate, yellow
V = 2519.5 (2) Å30.51 × 0.38 × 0.02 mm
Z = 4
Data collection top
Oxford Diffraction Gemini
diffractometer with Atlas CCD detector		3838 independent reflections
Radiation source: X-ray tube3428 reflections with I > 3σ(I)
mirrorsRint = 0.016
Detector resolution: 20.7567 pixels mm-1θmax = 61.4°, θmin = 3.2°
Rotation method data acquisition using ω scansh = −8→8
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)		k = −62→62
Tmin = 0.682, Tmax = 0.99l = −6→6
15440 measured reflections
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: difference Fourier map
wR(F2) = 0.120H-atom parameters constrained
S = 2.32Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
3838 reflections(Δ/σ)max = 0.001
317 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.18 e Å−3
112 constraints
Crystal data top
C32H28N2OV = 2519.5 (2) Å3
Mr = 456.6Z = 4
Monoclinic, P21/nCu Kα radiation
a = 7.4737 (3) ŵ = 0.56 mm−1
b = 55.929 (3) ÅT = 295 K
c = 6.0275 (3) Å0.51 × 0.38 × 0.02 mm
β = 90.022 (4)°
Data collection top
Oxford Diffraction Gemini
diffractometer with Atlas CCD detector		3838 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2008)		3428 reflections with I > 3σ(I)
Tmin = 0.682, Tmax = 0.99Rint = 0.016
15440 measured reflectionsθmax = 61.4°
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.120Δρmax = 0.19 e Å−3
S = 2.32Δρmin = −0.18 e Å−3
3838 reflectionsAbsolute structure: ?
317 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.41159 (19)0.25020 (2)1.1527 (2)0.0638 (4)
N10.4123 (2)0.33936 (3)0.7401 (3)0.0617 (5)
N20.4264 (2)0.16126 (3)0.7377 (3)0.0623 (5)
C10.4131 (2)0.27183 (3)1.0403 (3)0.0548 (5)
C20.4984 (2)0.29047 (3)1.1464 (3)0.0613 (6)
C30.4970 (2)0.31299 (3)1.0534 (3)0.0635 (6)
C40.4118 (2)0.31709 (3)0.8503 (3)0.0568 (5)
C50.3295 (2)0.29795 (3)0.7467 (3)0.0601 (6)
C60.3268 (2)0.27553 (3)0.8402 (3)0.0616 (6)
C70.4096 (2)0.35875 (3)0.8483 (3)0.0636 (6)
C80.4215 (2)0.38208 (3)0.7420 (3)0.0600 (6)
C90.4227 (2)0.40156 (3)0.8727 (3)0.0639 (6)
C100.4388 (2)0.42689 (3)0.8176 (3)0.0602 (6)
C110.5287 (3)0.43555 (4)0.6318 (4)0.0723 (7)
C120.5396 (3)0.45964 (4)0.5896 (4)0.0859 (9)
C130.4641 (3)0.47591 (4)0.7318 (4)0.0875 (9)
C140.3778 (3)0.46796 (4)0.9185 (4)0.0842 (8)
C150.3661 (3)0.44386 (4)0.9620 (4)0.0712 (7)
C160.4273 (3)0.38214 (4)0.4939 (3)0.0780 (8)
C170.4135 (2)0.22865 (3)1.0395 (3)0.0555 (5)
C180.3308 (2)0.20971 (3)1.1439 (3)0.0613 (6)
C190.3356 (2)0.18727 (3)1.0517 (3)0.0628 (6)
C200.4223 (2)0.18353 (3)0.8484 (3)0.0574 (5)
C210.5012 (2)0.20285 (3)0.7441 (3)0.0606 (6)
C220.5005 (2)0.22525 (3)0.8389 (3)0.0612 (6)
C230.4375 (2)0.14192 (4)0.8456 (3)0.0648 (6)
C240.4369 (2)0.11855 (3)0.7384 (3)0.0609 (6)
C250.4481 (2)0.09907 (3)0.8688 (3)0.0644 (6)
C260.4490 (2)0.07366 (3)0.8136 (3)0.0612 (6)
C270.3678 (3)0.06393 (4)0.6255 (4)0.0716 (7)
C280.3726 (3)0.03972 (4)0.5842 (4)0.0843 (8)
C290.4589 (3)0.02459 (4)0.7274 (4)0.0854 (8)
C300.5381 (3)0.03360 (4)0.9145 (4)0.0862 (9)
C310.5324 (3)0.05778 (4)0.9586 (4)0.0741 (7)
C320.4306 (3)0.11845 (4)0.4907 (3)0.0773 (8)
H20.5586920.2877651.2847870.0735*
H30.5550120.3259791.1287550.0762*
H50.2726970.3003910.6056230.0721*
H60.2657790.2626080.767520.0739*
H110.5840730.4244770.5313630.0868*
H120.6007380.465150.4591630.1031*
H130.4717120.4927230.7008980.105*
H140.3251980.4792571.019140.1011*
H150.3068210.4385871.0945480.0855*
H180.269530.2122261.2818990.0736*
H190.2794150.1741151.1266140.0753*
H210.5577680.2006010.6026120.0728*
H220.5595530.2383630.766850.0734*
H270.3073930.0743050.5230360.0859*
H280.3152010.0334140.4542390.1011*
H290.4638020.007760.6967170.1024*
H300.5979980.0230171.015510.1035*
H310.5867830.0637831.0916860.0889*
H70.3992030.3580451.0069140.0763*
H90.4109470.3982591.0283380.0767*
H230.4465970.1426631.0042790.0778*
H250.4570480.1024631.0244920.0773*
H16a0.3593470.368880.4380360.0936*
H16b0.377140.3968080.4393360.0936*
H16c0.5491680.3807820.4452480.0936*
H32a0.4932570.1321620.4346810.0927*
H32b0.4863020.1041480.4359390.0927*
H32c0.3083130.1189630.4422920.0927*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0715 (8)0.0641 (7)0.0559 (7)−0.0001 (5)0.0032 (7)0.0004 (6)
N10.0581 (8)0.0672 (9)0.0598 (9)−0.0006 (6)0.0011 (7)0.0000 (7)
N20.0611 (8)0.0675 (9)0.0585 (9)−0.0007 (7)0.0045 (7)0.0004 (7)
C10.0445 (8)0.0641 (10)0.0559 (9)0.0018 (7)0.0061 (7)−0.0017 (8)
C20.0571 (9)0.0713 (11)0.0554 (9)0.0006 (8)−0.0064 (8)−0.0025 (9)
C30.0600 (10)0.0670 (11)0.0634 (11)−0.0034 (8)−0.0054 (8)−0.0080 (9)
C40.0503 (8)0.0659 (10)0.0543 (9)0.0003 (7)0.0039 (8)−0.0023 (8)
C50.0541 (9)0.0719 (11)0.0543 (9)0.0012 (7)−0.0042 (8)−0.0032 (8)
C60.0505 (8)0.0688 (11)0.0655 (11)−0.0027 (7)−0.0066 (8)−0.0065 (9)
C70.0698 (11)0.0701 (11)0.0508 (9)0.0010 (8)0.0035 (9)0.0014 (9)
C80.0553 (9)0.0703 (11)0.0543 (10)0.0018 (8)0.0024 (8)0.0043 (8)
C90.0703 (11)0.0720 (11)0.0495 (9)0.0028 (8)0.0028 (8)0.0042 (9)
C100.0555 (9)0.0704 (11)0.0547 (10)0.0015 (8)−0.0040 (8)0.0020 (8)
C110.0742 (11)0.0766 (13)0.0662 (11)0.0011 (9)0.0119 (10)0.0048 (10)
C120.0964 (15)0.0807 (14)0.0807 (15)−0.0061 (11)0.0132 (12)0.0151 (11)
C130.0925 (15)0.0701 (13)0.1000 (17)−0.0013 (11)−0.0004 (14)0.0106 (12)
C140.0870 (14)0.0745 (13)0.0912 (16)0.0068 (10)0.0064 (13)−0.0108 (12)
C150.0702 (12)0.0789 (13)0.0645 (11)−0.0009 (9)0.0054 (9)−0.0040 (9)
C160.0973 (16)0.0812 (13)0.0555 (11)−0.0032 (11)0.0008 (11)0.0019 (9)
C170.0456 (8)0.0639 (10)0.0572 (9)0.0009 (7)−0.0010 (7)0.0014 (8)
C180.0559 (9)0.0714 (11)0.0568 (10)0.0012 (8)0.0096 (8)0.0040 (9)
C190.0580 (9)0.0670 (11)0.0634 (11)−0.0028 (8)0.0117 (8)0.0062 (9)
C200.0493 (8)0.0668 (10)0.0562 (9)0.0013 (7)0.0027 (8)0.0026 (8)
C210.0560 (9)0.0718 (11)0.0541 (9)0.0001 (7)0.0104 (8)0.0029 (8)
C220.0539 (9)0.0674 (11)0.0623 (10)−0.0032 (7)0.0109 (8)0.0061 (8)
C230.0715 (11)0.0708 (11)0.0522 (9)0.0025 (8)0.0015 (9)−0.0015 (9)
C240.0593 (10)0.0709 (11)0.0524 (10)0.0004 (8)0.0033 (8)−0.0021 (8)
C250.0706 (11)0.0733 (11)0.0493 (9)−0.0008 (8)0.0002 (8)−0.0044 (9)
C260.0570 (9)0.0723 (11)0.0543 (10)−0.0016 (8)0.0022 (8)−0.0002 (8)
C270.0707 (11)0.0774 (12)0.0667 (12)−0.0016 (9)−0.0099 (10)−0.0022 (10)
C280.0925 (15)0.0827 (14)0.0776 (14)−0.0149 (11)−0.0013 (12)−0.0131 (12)
C290.0934 (15)0.0725 (13)0.0901 (16)−0.0043 (11)0.0137 (13)−0.0041 (12)
C300.0947 (15)0.0747 (13)0.0892 (16)0.0011 (11)−0.0021 (13)0.0167 (12)
C310.0793 (13)0.0799 (14)0.0630 (11)−0.0062 (10)−0.0057 (10)0.0078 (10)
C320.0954 (15)0.0798 (13)0.0567 (11)−0.0036 (11)0.0032 (11)−0.0016 (9)
Geometric parameters (Å, °) top
O1—C11.386 (2)C16—H16a0.96
O1—C171.385 (2)C16—H16b0.96
N1—C41.412 (2)C16—H16c0.96
N1—C71.266 (2)C17—C181.378 (2)
N2—C201.414 (2)C17—C221.386 (3)
N2—C231.264 (2)C18—C191.373 (3)
C1—C21.379 (2)C18—H180.96
C1—C61.384 (3)C19—C201.402 (3)
C2—C31.379 (3)C19—H190.96
C2—H20.96C20—C211.383 (3)
C3—C41.398 (3)C21—C221.377 (3)
C3—H30.96C21—H210.96
C4—C51.384 (2)C22—H220.96
C5—C61.375 (3)C23—C241.458 (3)
C5—H50.96C23—H230.96
C6—H60.96C24—C251.346 (3)
C7—C81.456 (3)C24—C321.494 (3)
C7—H70.96C25—C261.459 (3)
C8—C91.345 (3)C25—H250.96
C8—C161.496 (3)C26—C271.396 (3)
C9—C101.460 (3)C26—C311.393 (3)
C9—H90.96C27—C281.377 (3)
C10—C111.393 (3)C27—H270.96
C10—C151.398 (3)C28—C291.370 (3)
C11—C121.374 (3)C28—H280.96
C11—H110.96C29—C301.370 (4)
C12—C131.372 (3)C29—H290.96
C12—H120.96C30—C311.379 (3)
C13—C141.372 (4)C30—H300.96
C13—H130.96C31—H310.96
C14—C151.376 (3)C32—H32a0.96
C14—H140.96C32—H32b0.96
C15—H150.96C32—H32c0.96
C1—O1—C17121.25 (14)H16b—C16—H16c109.4707
C4—N1—C7120.89 (16)O1—C17—C18116.07 (16)
C20—N2—C23120.83 (16)O1—C17—C22123.64 (15)
O1—C1—C2115.92 (15)C18—C17—C22120.20 (16)
O1—C1—C6123.52 (15)C17—C18—C19120.40 (17)
C2—C1—C6120.45 (16)C17—C18—H18119.7986
C1—C2—C3119.92 (17)C19—C18—H18119.8003
C1—C2—H2120.0388C18—C19—C20120.14 (16)
C3—C2—H2120.0374C18—C19—H19119.9296
C2—C3—C4120.58 (17)C20—C19—H19119.9325
C2—C3—H3119.7093N2—C20—C19123.66 (15)
C4—C3—H3119.7097N2—C20—C21117.67 (16)
N1—C4—C3123.73 (15)C19—C20—C21118.60 (16)
N1—C4—C5118.11 (16)C20—C21—C22121.35 (17)
C3—C4—C5118.09 (16)C20—C21—H21119.326
C4—C5—C6121.81 (17)C22—C21—H21119.3271
C4—C5—H5119.0935C17—C22—C21119.28 (16)
C6—C5—H5119.0919C17—C22—H22120.3631
C1—C6—C5119.12 (16)C20—C22—H22149.7198
C1—C6—H6120.4391N2—C23—C24122.61 (18)
C5—C6—H6120.4404N2—C23—H23118.6934
N1—C7—C8122.68 (17)C24—C23—H23118.6931
N1—C7—H7118.6563C23—C24—C25117.85 (17)
C8—C7—H7118.6616C23—C24—C32116.50 (16)
C7—C8—C9117.94 (17)C25—C24—C32125.61 (17)
C7—C8—C16116.35 (16)C24—C25—C26130.95 (17)
C9—C8—C16125.70 (17)C24—C25—H25114.5252
C8—C9—C10130.80 (17)C26—C25—H25114.5237
C8—C9—H9114.598C25—C26—C27124.25 (17)
C10—C9—H9114.6038C25—C26—C31118.67 (17)
C9—C10—C11124.07 (17)C27—C26—C31117.06 (18)
C9—C10—C15119.02 (17)C26—C27—C28121.3 (2)
C11—C10—C15116.87 (18)C26—C27—H27119.375
C10—C11—C12121.3 (2)C28—C27—H27119.3729
C10—C11—H11119.3764C27—C28—C29120.4 (2)
C12—C11—H11119.3736C27—C28—H28119.8062
C11—C12—C13120.7 (2)C29—C28—H28119.8072
C11—C12—H12119.6501C28—C29—C30119.7 (2)
C13—C12—H12119.6503C28—C29—H29120.1738
C12—C13—C14119.4 (2)C30—C29—H29120.1722
C12—C13—H13120.2841C29—C30—C31120.4 (2)
C14—C13—H13120.2831C29—C30—H30119.7998
C13—C14—C15120.3 (2)C31—C30—H30119.7949
C13—C14—H14119.8703C26—C31—C30121.2 (2)
C15—C14—H14119.8702C26—C31—H31119.3916
C10—C15—C14121.5 (2)C30—C31—H31119.3905
C10—C15—H15119.2735C24—C32—H32a109.4703
C14—C15—H15119.2764C24—C32—H32b109.4721
C8—C16—H16a109.4718C24—C32—H32c109.4709
C8—C16—H16b109.4708H32a—C32—H32b109.4716
C8—C16—H16c109.4712H32a—C32—H32c109.4711
H16a—C16—H16b109.4705H32b—C32—H32c109.4713
H16a—C16—H16c109.4723
?—?—?—??
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
?—?···?????
Acknowledgements top

We thank Gorgan University of Agricultural Sciences and Natural Resources (GUASNR) and the Institute of Physics of the ASCR (grant No. 202/07/J007) for supporting this study. ADK thanks Dr Jan Fabry (Institute of Physics of ASCR) for his collaboration.

references
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