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Synthesis, Characterization, and Crystal Structure of (2E)-3-(4-Fluorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

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Abstract

The title chalcone, of formula C15H11F1O2, crystallized in the orthorhombic space group P212121 (# 19) with crystal parameters a = 6.9998(8) Å, b = 12.6740(15) Å, c = 12.8997(15) Å, V = 1144.4(2) Å3, Z = 4, determined at 100 K with MoKα radiation. The solid-state structure displays an intramolecular S(6) hydrogen bond and the crystal architecture is maintained by intermolecular F⋯H, O⋯H, and C⋯C short contacts. A DFT geometry optimization is compared with the experimental structure. As 19F NMR spectroscopy can be used for metabolic tagging of biologically active compounds (including chalcones), the solution-state 19F chemical shift and 13C19F coupling constants (nJ) are also reported.

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Acknowledgements

The authors acknowledge the support of the University of KwaZulu-Natal (Pietermaritzburg) and the National Research Foundation (NRF) of South Africa.

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Authors and Affiliations

  1. School of Chemistry, University of the Witwatersrand, Johannesburg, South Africa

    Cathryn A. Slabber & Orde Q. Munro

  2. School of Chemistry and Physics, University of KwaZulu-Natal, Pietermaritzburg, South Africa

    Craig D. Grimmer & Ross S. Robinson

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  1. Cathryn A. Slabber
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Correspondence to Ross S. Robinson.

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10870_2018_732_MOESM1_ESM.pdf

Supplementary material 1. Supplementary information in the form of crystallographic data (CCDC 1048845) may be obtained via the web at the URL http://www.ccdc.cam.ac.uk/, via email from data_request@ccdc.cam, or by contacting the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB21FZ, United Kindgom. (PDF 1841 KB)

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Slabber, C.A., Grimmer, C.D., Munro, O.Q. et al. Synthesis, Characterization, and Crystal Structure of (2E)-3-(4-Fluorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one. J Chem Crystallogr 48, 213–219 (2018). https://doi.org/10.1007/s10870-018-0732-4

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