2-[1-(1-Naphthyl)-1H-1,2,3-triazol-4-yl]pyridine

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(1)2-[1-(1-Naphthyl)-1H-1,2,3-triazol-4-yl]pyridine Citation for published version (APA): Happ, B., Hoogenboom, R., Winter, A., Hager, M. D., Baumann, S. O., Kickelbick, G., & Schubert, U. S. (2009). 2-[1-(1-Naphthyl)-1H-1,2,3-triazol-4-yl]pyridine. Acta Crystallographica, Section E: Structure Reports, E65(5), o1146-sup-8. https://doi.org/10.1107/S160053680901407X. DOI: 10.1107/S160053680901407X Document status and date: Published: 01/01/2009 Document Version: Publisher’s PDF, also known as Version of Record (includes final page, issue and volume numbers) Please check the document version of this publication: • A submitted manuscript is the version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. People interested in the research are advised to contact the author for the final version of the publication, or visit the DOI to the publisher's website. • The final author version and the galley proof are versions of the publication after peer review. • The final published version features the final layout of the paper including the volume, issue and page numbers. Link to publication. General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. • Users may download and print one copy of any publication from the public portal for the purpose of private study or research. • You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal. If the publication is distributed under the terms of Article 25fa of the Dutch Copyright Act, indicated by the “Taverne” license above, please follow below link for the End User Agreement: www.tue.nl/taverne. Take down policy If you believe that this document breaches copyright please contact us at: openaccess@tue.nl providing details and we will investigate your claim.. Download date: 04. Oct. 2021.

(2) electronic reprint Acta Crystallographica Section E. Structure Reports Online ISSN 1600-5368. Editors: W.T. A. Harrison, J. Simpson and M. Weil. 2-[1-(1-Naphthyl)-1H -1,2,3-triazol-4-yl]pyridine Bobby Happ, Richard Hoogenboom, Andreas Winter, Martin D. Hager, Stefan O. Baumann, Guido Kickelbick and Ulrich S. Schubert. Acta Cryst. (2009). E65, o1146. This open-access article is distributed under the terms of the Creative Commons Attribution Licence http://creativecommons.org/licenses/by/2.0/uk/legalcode, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.. ISSN 1600-5368. Volume 61 Part 11 November 2005. Acta Crystallographica Section E. Structure Reports Online Editors: W. Clegg and D. G. Watson. Inorganic compounds. Metal-organic compounds. Organic compounds. journals.iucr.org International Union of Crystallography. *. Acta Crystallographica Section E: Structure Reports Online is the IUCr’s highly popular open-access structural journal. It provides a simple and easily accessible publication mechanism for the growing number of inorganic, metal-organic and organic crystal structure determinations. The electronic submission, validation, refereeing and publication facilities of the journal ensure very rapid and high-quality publication, whilst key indicators and validation reports provide measures of structural reliability. In 2007, the journal published over 5000 structures. The average publication time is less than one month.. Chester. Crystallography Journals Online is available from journals.iucr.org Acta Cryst. (2009). E65, o1146. Happ et al. · C17 H12 N4.

(3) organic compounds Acta Crystallographica Section E. Data collection. Structure Reports Online ISSN 1600-5368. Bruker Kappa APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2008a) Tmin = 0.950, Tmax = 0.994. 2-[1-(1-Naphthyl)-1H-1,2,3-triazol-4-yl]pyridine. Refinement. Bobby Happ,a Richard Hoogenboom,b Andreas Winter,b Martin D. Hager,a Stefan O. Baumann,c Guido Kickelbickc and Ulrich S. Schuberta,b* a. Laboratory of Organic and Macromolecular Chemistry, Friedrich-Schiller-Universita¨t Jena, Humboldtstrasse 10, 07743 Jena, Germany, bEindhoven University of Technology, Laboratory of Macromolecular Chemistry and Nanoscience, Den Dolech 2, NL-5612AZ Eindhoven, The Netherlands, and cVienna University of Technology, Institute of Materials Chemistry, Getreidemarkt 9/165, 1060 Wien, Austria Correspondence e-mail: ulrich.schubert@uni-jena.de Received 2 April 2009; accepted 15 April 2009 ˚; Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.002 A R factor = 0.035; wR factor = 0.120; data-to-parameter ratio = 12.6.. In the crystal structure of the title compound, C17H12N4, the angle between the naphthalene and 1H-1,2,3-triazole ring systems is 71.02 (4) and that between the pyridine and triazole rings is 8.30 (9) .. Related literature For related literature on the synthesis of polypyridyl ligands and 1,2,3-triazole-containing compounds, see: Marin et al. (2007); Winter et al. (2007); Balzani et al. (1996); Newkome et al. (2004); Chan et al. (2004); Rostovtsev et al. (2002); Kolb et al. (2001). The synthesis of the title compound is reported in Happ et al. (2009). For related crystal structures, see: Obata et al. (2008); Schweinfurth et al. (2008); Schulze et al. (2009); Li et al. (2007); Richardson et al. (2008); Angell & Burgess (2007).. Experimental Crystal data C17H12N4 Mr = 272.31 Orthorhombic, Pbca ˚ a = 11.6378 (4) A ˚ b = 9.3228 (4) A ˚ c = 25.0592 (9) A. o1146. Happ et al.. ˚3 V = 2718.84 (18) A Z=8 Mo K radiation = 0.08 mm 1 T = 296 K 0.63 0.18 0.07 mm. R[F 2 > 2(F 2)] = 0.035 wR(F 2) = 0.120 S = 1.01 2391 reflections. 14517 measured reflections 2391 independent reflections 1934 reflections with I > 2(I) Rint = 0.027. 190 parameters H-atom parameters constrained ˚ 3 max = 0.14 e A ˚ 3 min = 0.18 e A. Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: CARINE (Boudias & Monceau, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).. This structure examination is part of ongoing work financially supported by the Dutch Polymer Institute (DPI), the Nederlandse Organisatie voor Wetenschappelijk Onderzoek (NWO, VICI award to USS) and the Fonds der Chemischen Industrie. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2322).. References Angell, Y. & Burgess, K. (2007). Angew. Chem. Int. Ed. 46, 3649–3651. Balzani, V., Juris, A. & Venturi, M. (1996). Chem. Rev. 96, 759–833. Boudias, C. & Monceau, D. (1998). CARINE. Carine Crystallography, Divergent S. A., Compie`gne, France. Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Chan, T. R., Hilgraf, R., Sharpless, K. B. & Fokin, V. V. (2004). Org. Lett. 6, 2853–2855. Happ, B., Friebe, C., Winter, A., Hager, M. D., Hoogenboom, R. & Schubert, U. S. (2009). Chem. Asian J. 4, 154–163. Kolb, H. C., Finn, M. G. & Sharpless, K. B. (2001). Angew. Chem. Int. Ed. 40, 2004–2021. Li, Y., Huffman, J. C. & Flood, A. H. (2007). Chem. Commun. pp. 2692–2694. Marin, V., Holder, E., Hoogenboom, R. & Schubert, U. S. (2007). Chem. Soc. Rev. 36, 618–635. Newkome, G. R., Patri, A. K., Holder, E. & Schubert, U. S. (2004). Eur. J. Org. Chem. pp. 235–254. Obata, M., Kitamura, A., Mori, A., Kameyama, C., Czaplewska, J. A., Tanaka, R., Kinoshita, I., Kusumoto, T., Hashimoto, H., Harada, M., Mikata, Y., Funabiki, T. & Yano, S. (2008). Dalton Trans. pp. 3292–3300. Richardson, C., Fitchett, C. M., Keene, F. R. & Steel, P. J. (2008). Dalton Trans. pp. 2534–2537. Rostovtsev, V. V., Green, L. G., Fokin, V. V. & Sharpless, K. B. (2002). Angew. Chem. Int. Ed. 41, 2596–2599. Schulze, B., Friebe, C., Hager, M. D., Winter, A., Hoogenboom, R., Goerls, H. & Schubert, U. S. (2009). Dalton Trans. pp. 787–794. Schweinfurth, D., Hardcastle, K. I. & Bunz, U. H. F. (2008). Chem. Commun. pp. 2203–2205. Sheldrick, G. M. (2008a). SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (2008b). Acta Cryst. A64, 112–122. Winter, A., Egbe, D. A. M. & Schubert, U. S. (2007). Org. Lett. 9, 2345–2348.. doi:10.1107/S160053680901407X. electronic reprint. Acta Cryst. (2009). E65, o1146.

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