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Synthesis and crystal structures of two novel triazolopyridine compounds solved by local L.S. minimizations from powder diffraction data

  • Oriol Vallcorba (a1), Rosa Adam (a2), Jordi Rius (a1), Rafael Ballesteros (a2), José M. Amigó (a3) and Belén Abarca (a2)...

Abstract

The heteroaryl-substituted triazolopyridines 3-phenyl-7-(pyrazin-2-yl)-[1,2,3]triazolo[1,5-a]pyridine (2) and 3-[6-(pyridazin-3-yl)-pyridin-2-yl]-[1,2,3]triazolo[1,5-a]pyridine (4) have been synthesized and characterized (by HRMS, IR, 1H and 13C NMR, XRPD, melting point). The crystal structures have been solved from laboratory powder X-ray diffraction data with the direct-space strategy TALP for molecular compounds based on fast local least-squares minimizations. The crystal structure confirmed the formation of the tridentate compound 4 from a ring chain isomerization process. The almost planar arrangement of atoms in both the structures favors the presence of intermolecular ππ interactions, although weak C–H···N electrostatic interactions seem to be also important for the stabilization of the structure. Powder diffraction data have also proved to be sensible enough to determine the relative rotations of the six-membered rings despite the weak difference in scattering power between C and N atoms.

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Corresponding author

a) Author to whom correspondence should be addressed. Electronic mail: ovallcorba@icmab.es

References

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Abarca, B., Ballesteros, R., and Elmasnaouy, M. (1998). “A facile route to new potential helicating ligands,” Tetrahedron 54, 1528715292.
Abarca, B., Ballesteros, R., and Chadlaoui, M. (2004). “Triazolopyridines. Part 24: new polynitrogenated potential helicating ligands,” Tetrahedron 60, 57855792.
Abarca, B., Alkorta, I., Ballesteros, R., Blanco, F., Chadlaoui, M., Elguero, J., and Mojarrad, F. (2005). “3-(2-Pyridyl)-[1,2,3]triazolo [1,5-a]pyridines. An experimental and theoretical (DFT) study of the ring–chain isomerization,” Org. Biomol. Chem. 3, 39053910.
Abarca, B., Aucejo, R., Ballesteros, R., Blanco, F., and García-España, E. (2006). “Synthesis of novel fluorescent 3-aryl-and 3-methyl-7-aryl-[1,2,3]triazolo[1,5-a] pyridines by Suzuki cross-coupling reactions,” Tetrahedron Lett. 47, 81018103.
Adam, R., Ballesteros-Garrido, R., Vallcorba, O., Abarca, B., Ballesteros, R., Leroux, F. R., Colobert, F., Amigó, J. M., and Rius, J. (2013). “Synthesis and structural properties of an hexaaza[5]helicene containing two [1,2,3]triazolo[1,5-a]pyridine moieties,” Tetrahedron Lett. 54, 43164319.
Arcís-Castillo, Z., Piñeiro-López, L., Muñoz, M. C., Ballesteros, R., Abarca, B., and Real, J. A. (2013). “Structural, magnetic and calorimetric studies of a crystalline phase of the spin crossover compound [Fe(tzpy)2(NCSe)2],” CrystEngComm 15, 34553462.
Ballesteros, R., Abarca, B., Samadi, A., Server-Carrió, J., and Escrivà, E. (1999). “Coordinating behaviour of 3-methyl[1,2,3]triazolo[1,5-a]pyridine (tzpy): crystal and molecular structure and electronic properties of [Cu(tzpy)2(ONO2)2(OH2)],” Polyhedron 18, 31293133.
Ballesteros-Garrido, R., Abarca, B., Ballesteros, R., de Arellano, C. R., Leroux, F. R., Colobert, F., and García-España, E. (2009). “[1,2,3]Triazolo[1,5-a]pyridine derivatives as molecular chemosensors for zinc (II), nitrite and cyanide anions,” New J. Chem. 33, 21022106.
Ballesteros-Garrido, R., Delgado-Pinar, E., Abarca, B., Ballesteros, R., Leroux, F. R., Colobert, F., Zaragozá, R. J., and García-España, E. (2012). “Triazolopyridines. Part 28. The ring–chain isomerization strategy: triazolopyridine- and triazoloquinoline–pyridine based fluorescence ligands,” Tetrahedron 68, 37013707.
Battaglia, L. P., Carcelli, M., Ferraro, F., Mavilla, L., Pelizzi, C., and Pelizzi, G. (1994). A convenient method for the preparation of 3-(2-pyridyl) triazolo[1,5-a]pyridine (L). Crystal structures of L and [CuL2(OH2)2][NO3]2 ,” J. Chem. Soc., Dalton Trans. 1994, 26512654.
Boultif, A. and Louër, D. (2004). “Powder pattern indexing with the dichotomy method,” J. Appl. Crystallogr. 37, 724731.
Boyer, J. and Goebel, N. (1960). “The identification of C12H8N4O, an oxidation product from α-pyridil monohydrazone,” J. Org. Chem. 25, 304305.
Cerný, R. and Favre-Nicolin, V. (2007). “Direct space methods of structure determination from powder diffraction: principles, guidelines and perspectives,” Z. Kristallogr. 222, 105113.
Chadlaoui, M., Abarca, B., Ballesteros, R., Ramírez de Arellano, C., Aguilar, J., Aucejo, R., and García-España, E. (2006). “Properties of a triazolopyridine system as a molecular chemosensor for metal ions, anions, and amino acids,” J. Org. Chem. 71, 90309034.
Jones, G. and Abarca, B. (2010). “The chemistry of the [1,2,3]triazolo[1,5-a]pyridines: an update,” Adv. Heterocycl. Chem. 100, 195252.
Jones, G. and Sliskovic, D. R. (1980). “[1,2,3]Triazolo[1,5-a]pyridine-a synthon for 6-substituted pyridine-2-carboxaldehydes,” Tetrahedron Lett. 21, 45294530.
Jones, G. and Sliskovic, D. R. (1982). “Triazolopyridines. Part 2. Preparation of 7-substituted triazolo[1,5-a]pyridines by directed lithiation,” J. Chem. Soc., Perkin Trans. 1, 967971.
Jones, G., Mouat, D. J., and Tonkinson, D. J. (1985). “Triazolopyridines. Part 6. Ring opening reactions of triazolopyridines,” J. Chem. Soc., Perkin Trans. 1, 27192723.
Jones, G., Pitman, M. A., Lunt, E., Lythgoe, D. J., Abarca, B., Ballesteros, R., and Elmasnaouy, M. (1997). “Triazolopyridines. 18. Nucleophilic substitution reactions on triazolopyridines; a new route to 2, 2′-bipyridines,” Tetrahedron 53, 82578268.
Kress, T. J. (1979). “Direct metalation of pyrimidine. Synthesis of some 4-substituted pyrimidines,” J. Org. Chem. 44, 20812082.
Mascal, M. (1998). “Statistical analysis of C–H···N hydrogen bonds in the solid state: there are real precedents,” Chem. Commun. 1998, 303304.
Niel, V., Gaspar, A. B., Muñoz, M. C., Abarca, B., Ballesteros, R., and Real, J. A. (2003). “Spin crossover behavior in the iron (II)-2-pyridyl[1,2,3]triazolo[1,5-a]pyridine system: X-ray structure, calorimetric, magnetic, and photomagnetic studies,” Inorg. Chem. 42, 47824788.
Ramírez de Arellano, C., Escrivà, E., Gómez-García, C. J., Mínguez Espallargas, G., Ballesteros, R., and Abarca, B. (2013). “Hydrogen bonding versus π-stacking in ferromagnetic interactions. Studies on a copper triazolopyridine complex,” CrystEngComm 15, 18361839.
Rius, J. (2013). RIBOLS: Least-Squares Refinement from Powder Diffraction Data, version 1310 (Computer Software) (Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Barcelona, Spain).
Thalladi, V. R., Gehrke, A., and Boese, R. (2000). “C–H group acidity and the nature of C–H···N interactions: crystal structural analysis of pyrazine and methyl substituted pyrazines,” New J. Chem. 24, 463470.
Vallcorba, O., Rius, J., Frontera, C., Peral, I., and Miravitlles, C. (2012a). “DAJUST: a suite of computer programs for pattern matching, space-group determination and intensity extraction from powder diffraction data,” J. Appl. Crystallogr. 45, 844848.
Vallcorba, O., Rius, J., Frontera, C., and Miravitlles, C. (2012b). “TALP: a multisolution direct-space strategy for solving molecular crystals from powder diffraction data based on restrained least squares,” J. Appl. Crystallogr. 45, 12701277.

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Synthesis and crystal structures of two novel triazolopyridine compounds solved by local L.S. minimizations from powder diffraction data

  • Oriol Vallcorba (a1), Rosa Adam (a2), Jordi Rius (a1), Rafael Ballesteros (a2), José M. Amigó (a3) and Belén Abarca (a2)...

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