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Crystallographic Studies of Dehydration Phenomenon in Methyl 3-hydroxy-2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1λ 6-benzo[e][1,2]thiazine-3-carboxylate

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Abstract

Methyl 3-hydroxy-2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1λ6-benzo[e][1,2]thiazine-3-carboxylate was synthesized in single step through in situ bromination of methyl 2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1λ6-benzo[e][1,2]thiazine-3-carboxylate using dibenzoyl peroxide & N-bromosuccinamide and was crystallized in acetone-ethyl acetate mixture (1:1). However, crystallization in methanol converted the title compound to methyl 3-methoxy-2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1λ6-benzo[e][1,2]thiazine-3-carboxylate, an unsymmetrical ether. The titled compound C11H11NO6S (3) crystallized in nonoclinic space group P21/c whereas, the compound C12H13NO6S (4) crystallized in triclinic space group P-1. X-ray studies shows that the molecules of 1 are linked into a one-dimensional framework structure by C–H···O and O–H···O hydrogen bonds, while in 4, intermolecular C–H···O and C–H···π hydrogen bonds and a π···π interaction result in the formation of infinite chains running along the [010] and [001] directions.

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Acknowledgments

The authors acknowledge the Centre for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah, Saudi Arabia and GC University, Lahore, Pakistan for supporting this study.

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Authors and Affiliations

  1. Chemistry Department & Centre of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, Jeddah, 21589, Saudi Arabia

    Muhammad Nadeem Arshad, Abdullah M. Asiri, Sher Bahadar Khan & Khalid A. Alamry

  2. Scientific and Technological Research Application and Research Center, Sinop University, 57010, Sinop, Turkey

    Onur Şahin

  3. Applied Chemistry Research Center, PCSIR Laboratories Complex, Ferozpur Road, Lahore, 54600, Pakistan

    Muhammad Zia-ur-Rehman

  4. Department of Chemistry, GC University, Faisalabad, 30800, Pakistan

    Muhammad Shafiq

  5. Materials Chemistry Laboratory, Department of Chemistry, GC University, Lahore, 54000, Pakistan

    Islam Ullah Khan

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  1. Muhammad Nadeem Arshad
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  2. Onur Şahin
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  3. Muhammad Zia-ur-Rehman
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  4. Muhammad Shafiq
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  5. Islam Ullah Khan
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  6. Abdullah M. Asiri
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  8. Khalid A. Alamry
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Correspondence to Muhammad Nadeem Arshad or Onur Şahin.

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Arshad, M.N., Şahin, O., Zia-ur-Rehman, M. et al. Crystallographic Studies of Dehydration Phenomenon in Methyl 3-hydroxy-2-methyl-1,1,4-trioxo-1,2,3,4-tetrahydro-1λ 6-benzo[e][1,2]thiazine-3-carboxylate. J Chem Crystallogr 43, 671–676 (2013). https://doi.org/10.1007/s10870-013-0471-5

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  • DOI: https://doi.org/10.1007/s10870-013-0471-5

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