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Zeitschrift für Kristallographie - New Crystal Structures

Editor-in-Chief: Huppertz, Hubert

Editorial Board: Hübschle, Christian / Janka, Oliver / Lemmerer, Andreas / Reiß, Guido / Tiekink, Edward R.T.


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2197-4578
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Volume 231, Issue 2

Issues

Crystal structure of 2,2′-[pentane-1,5-diylbis(oxy)]dibenzaldehyde, C19H20O4

Tomislav Balić
  • Corresponding author
  • Department of Chemistry, Josip Juraj Strossmayer University of Osijek, Cara, Hadrijana 8/A, 31000 Osijek, Croatia
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Berislav Marković
  • Department of Chemistry, Josip Juraj Strossmayer University of Osijek, Cara, Hadrijana 8/A, 31000 Osijek, Croatia
  • Other articles by this author:
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Published Online: 2016-02-26 | DOI: https://doi.org/10.1515/ncrs-2015-0213

Abstract

C19H20O4, monoclinic, P21/c (no. 14), a = 16.5979(5) Å, b = 8.5654(2) Å, c = 11.8418(4) Å, β = 108.537(4)°, V = 1596.18(8) Å3, Z = 4, Rgt(F) = 0.0385, wRref(F2) = 0.0973, T = 190 K.

This article offers supplementary material which is provided at the end of the article.

CCDC no.:: 1452071

The crystal structure is shown in the figure. Tables 13 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Table 2

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Table 3

Atomic coordinates and displacement parameters (Å2).

Source of material

Salicylaldehyde (0.1 mol) and K2CO3 (0.1 mol) were mixed in DMF and heated to boiling temperature. 0.05 mol of 1,5-dibromopentane dissolved in DMF were then added and the reaction mixture was refluxed for 4 h. After the reaction was complete, 500 mL of water were added and the resulting percipitate was filtered and washed with water. The product was recrystallized from absolute ethanol. Single crystals suitable for diffraction experiments were obtained by slow evaporation of an ethanol solution.

Experimental details

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å and with Uiso(H) = 1.2 times Ueq(C).

Discussion

Aldehydes comprising two carbonyl functional groups (so called two-arm aldehydes) are promising starting materials for synthesis of macrocyclic Schiff bases. Condensation reactions of ortho substituted dialdehydes with primary amines and ketones have been recently investigated for preparation of complex macrocyclic compounds [1, 2], porous organic materials [3] and macrocyclic chalcones [4]. The title molecule is comprised of two formylphenoxy groups linked by five methylene carbon atoms (see the figure). The benzaldehyde groups enclose a dihedral angle of 67.5(6)° and therefore the molecule is non-planar. It is interesting to note, as reported in our previous contributions [5, 6], as well as in other related studies [79], that similar dialdehydes with even number of atoms in the aliphatic chain are planar, while molecules with odd number of atoms are non-planar. These deviations cause differences in some properties of these dialdehydes, such as melting point and crystal packing arrangement. In the crystal, the molecules are linked into dimers through weak C—H⋯O hydrogen bonds [graph set R22(28)] [10]. These dimers are connected into chains along [101] direction via weak C—H⋯O interactions. Additional stabilization of the crystal structure is achieved by a number of weak C—H⋯O and C—H⋯π interactions which are linking the chains of dimers.

Acknowledgements:

The authors wish to thank prof. Dubravka Matković-Čalogović for all the help during data collection and structure refinement.

References

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About the article

Corresponding author: Tomislav Balić, Department of Chemistry, Josip Juraj Strossmayer University of Osijek, Cara, Hadrijana 8/A, 31000 Osijek, Croatia, e-mail:


Received: 2015-09-10

Accepted: 2016-02-07

Published Online: 2016-02-26

Published in Print: 2016-06-01


Citation Information: Zeitschrift für Kristallographie - New Crystal Structures, Volume 231, Issue 2, Pages 619–621, ISSN (Online) 2197-4578, ISSN (Print) 1433-7266, DOI: https://doi.org/10.1515/ncrs-2015-0213.

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©2016 Tomislav Balić et al., published by De Gruyter.. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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