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Crystal Structure of 3-(4-Methoxy-benzylidene)-isothiochroman-4-one

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Abstract

The title compound, 3-(4-methoxy-benzylidene)-isothiochroman-4-one (C17H14O2S) was prepared from the reaction of isothiochroman-4-one with benzaldehyde in the presence of small amount of HCl. The structure of the synthesised compound was determined by IR, 1H NMR and X-ray crystallography. The structure was solved in monoclinic, space group P21/n with a = 3.9773 (7) Å, b = 10.918 (2) Å, c = 30.609 (6) Å, β = 90.615 (3)°, V = 1329.1 (4) Å3, Z = 4 and with R int = 0.047. The bicyclic ring of isothiochroman-4-one moiety does not adopt a planar geometry. The molecular conformation is stable via C10–H···O1 and C16–H···S1 intramolecular hydrogen-bonding interactions. These contacts involve molecules in an extended two-dimensional sheet to the bc plane.

Graphical Abstract

3-(4-Methoxybenzylidene)isothiochroman-4-one (C17H14O2S) was prepared from the reaction of isothiochroman-4-one with benzaldehyde in the presence of small amount of HCl. The structure of the synthesized compound was determined by IR, 1H NMR and X-ray crystallography. The bicyclic ring of isothiochroman-4-one does not adopt a planar geometry. The molecular conformation is stable via intramolecular hydrogen-bonding.

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Scheme 1
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Acknowledgments

This work was supported by the Program du Projet Global de Recherche de l’Universite′ Mohamed Premier d’Oujda ‘PGR-BH-20050 and PARS CO4 Grants from the Ministry of National Education of Morocco.

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Authors and Affiliations

  1. Department of Physics, F.A.S., Erciyes University, 38039, Kayseri, Turkey

    M. Akkurt & S. Ö. Yıldırım

  2. Laboratoire de Chimie Organique, Faculté des Sciences Dhar El Mehraz, Fes, Morocco

    A. Kerbal & B. Bennani

  3. Laboratoire de Chimie des Matériaux, Université Mohammed Premier, Oujda, Morocco

    T. Ben Hadda

  4. Department of Chemistry, Bahauddin Zakariya University, Multan, Pakistan

    Z. H. Chohan

  5. Department of Chemistry, Loughborough University, Leicestershire, LE11 3TU, UK

    Vickie McKee

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  1. M. Akkurt
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  2. S. Ö. Yıldırım
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  3. A. Kerbal
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  4. B. Bennani
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  5. T. Ben Hadda
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  6. Z. H. Chohan
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  7. Vickie McKee
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Correspondence to M. Akkurt or Z. H. Chohan.

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Akkurt, M., Yıldırım, S.Ö., Kerbal, A. et al. Crystal Structure of 3-(4-Methoxy-benzylidene)-isothiochroman-4-one. J Chem Crystallogr 40, 165–168 (2010). https://doi.org/10.1007/s10870-009-9628-7

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  • DOI: https://doi.org/10.1007/s10870-009-9628-7

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