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.
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).
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  and macrocyclic chalcones . 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 [7–9], 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)] . These dimers are connected into chains along  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.
The authors wish to thank prof. Dubravka Matković-Čalogović for all the help during data collection and structure refinement.
Balić, T.; Marković, B.; Jaźwiński, J.; Matković-Čalogović, D.: Synthesis and structural characterization of new N2O2-donor Schiff base macrocycles and their silver(I) coordination polymers. Inorg. Chim. Acta 435 (2015) 283–291. Web of ScienceGoogle Scholar
Ilhan, S.; Temel, H.; Yilmaz, I.; Kilic, A.: Synthesis, characterization and redox properties of macrocyclic Schiff base by reaction of 2,6-diaminopyridine and 1,3-bis(2-carboxyaldehydephenoxy)propane and its Cu(II), Ni(II), Pb(II), Co(III) and La(III) complexes. Transition Met. Chem. 32 (2007) 344–349. Web of ScienceGoogle Scholar
Mondal, R., Mandal, T. K.; Mallik, A. K.: Simple synthesis of a new family of 22- to 28-membered macrocycles containing two chalcone moieties. Arkivoc 13 (2012) 95–110. Google Scholar
Balić, T.; Marković, B.; Balić, I.: 4-[5-(4-Formylphenoxy)pentoxy] benzaldehyde. Acta Crystallogr. E68 (2012) 2664. Google Scholar
Balić, T.; Marković, B.; Balić, I.: Triclinic polymorph of 4-[4-(4-formylphenoxy)butoxy]benzaldehyde. Acta Crystallogr. E69 (2013) 126. Google Scholar
Ali, Q.; Raza Shah, M.; Ng, S. W.: 4,4′-(Propane-1,3-diyldioxy) dibenzaldehyde. Acta Crystallogr. E66 (2010) 1620. Google Scholar
Dehno Khalaji, A.; Hafez Ghoran, S.; Gotoh, K.; Ishida, H.: 2-[4-(2-Formylphenoxy)butoxy]benzaldehyde. Acta Crystallogr. E67 (2011) o2484.Google Scholar
Han, J.-R.; Zhen, X.-L.: 4-[4-(4-Formylphenoxy)butoxy]benzaldehyde. Acta Crystallogr. E61 (2005) 4358–4359. Google Scholar
Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L.: Patterns in hydrogen bonding: functionality and graph set analysis in crystals. Angew. Chem. Int. Ed. 34 (1995) 1555–1573. Google Scholar
Oxford Diffraction: CrysAlisPRO CCD and CrysAlisPRO RED, including ABSPACK. Oxford Diffraction Ltd, Yarnton, England, 2009. Google Scholar
Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; DeCaro, L.; Giacovazzo, C.; Polidori, G.; Spagna, R.: SIR2004: an improved tool for crystal structure determination and refinement. J. Appl. Cryst. 38 (2005) 381–388. Google Scholar
Burnett, M. N.; Johnson, C. K.: ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895, 1996. Google Scholar
About the article
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.
©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