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Volume 65 
Part 3 
Page o538  
March 2009  

Received 10 February 2009
Accepted 11 February 2009
Online 18 February 2009

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Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.120
Data-to-parameter ratio = 12.1
Details
Open access

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

Mansoor Movahedi,a Hassan Hadadzadeh,b Karla Fejfarova,c Michal Dusekc* and Aliakbar Dehno Khalajid

aDepartment of Science, Golestan University, Gorgan, Iran,bDepartment of Chemistry, Isfahan University of Technology, Isfahan 84156-83111, Iran,cInstitute of Physics of the ASCR, Na Slovance 2, 182 21 Prague 8, Czech Republic, and dDepartment of Science, Gorgan University of Agricultural Sciences and Natural Resources, Gorgan 49189-43464, Iran
Correspondence e-mail: dusek@fzu.cz

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)°.

Related literature

For the synthesis of the title compound, see: Khalaji & Ng (2008[Khalaji, A. D. & Ng, S. W. (2008). Acta Cryst. E64, o1771.]). For related structures, see: Hu et al. (2008[Hu, S.-L., Li, Y.-T. & Cao, L.-P. (2008). Acta Cryst. E64, o115.]); Xu et al. (2008[Xu, H.-W., Li, J.-X. & Li, Y.-H. (2008). Acta Cryst. E64, o1145.]). For background to transition metal complexes, see: Laye (2007[Laye, R. H. (2007). Inorg. Chim. Acta, 360, 439-447.]); Huang et al. (2005[Huang, Z., Tian, J.-L. & Bu, X. H. (2005). Inorg. Chem. Commun. 8, 194-198.]); Chu & Huang (2007[Chu, Z. & Huang, W. (2007). J. Mol. Struct. 837, 15-22.]).

[Scheme 1]

Experimental

Crystal data

  • C32H28N2O

  • Mr = 456.6

  • Monoclinic, P 21 /n

  • a = 7.4737 (3) Å

  • b = 55.929 (3) Å

  • c = 6.0275 (3) Å

  • [beta] = 90.022 (4)°

  • V = 2519.5 (2) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.56 mm-1

  • T = 295 K

  • 0.51 × 0.38 × 0.02 mm
Data collection

  • Oxford Diffraction Gemini diffractometer with Atlas CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.682, Tmax = 0.99

  • 15440 measured reflections

  • 3838 independent reflections

  • 3428 reflections with I > 3[sigma](I)

  • Rint = 0.016

  • [theta]max = 61.4°
Refinement

  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.120

  • S = 2.32

  • 3838 reflections

  • 317 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: JANA2006 (Petrícek et al., 2008[Petrícek, V., Dusek, M. & Palatinus, L. (2008). JANA2006. Institute of Physics, Praha, Czech Republic.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: JANA2006.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2870 ).

Acknowledgements

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

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [details]
Chu, Z. & Huang, W. (2007). J. Mol. Struct. 837, 15-22.  [ISI] [CSD] [CrossRef] [ChemPort]
Hu, S.-L., Li, Y.-T. & Cao, L.-P. (2008). Acta Cryst. E64, o115.  [CSD] [CrossRef] [details]
Huang, Z., Tian, J.-L. & Bu, X. H. (2005). Inorg. Chem. Commun. 8, 194-198.  [ISI] [CSD] [CrossRef] [ChemPort]
Khalaji, A. D. & Ng, S. W. (2008). Acta Cryst. E64, o1771.  [CSD] [CrossRef] [details]
Laye, R. H. (2007). Inorg. Chim. Acta, 360, 439-447.  [ISI] [CSD] [CrossRef] [ChemPort]
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Petrícek, V., Dusek, M. & Palatinus, L. (2008). JANA2006. Institute of Physics, Praha, Czech Republic.
Xu, H.-W., Li, J.-X. & Li, Y.-H. (2008). Acta Cryst. E64, o1145.  [CSD] [CrossRef] [details]

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

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