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Molecular and crystal structures of two 1,2,4-benzothiadiazine derivatives

  • Structure of Organic Compounds: Calculations and Experiments
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Abstract

The synthesis of two 1,2,4-benzothiadiazine derivatives, namely, 6-bromo-4H-spiro[1,2,4-benzothiadiazine- 3,1′-cyclobutane] 1,1-dioxide (1) and 6-bromo-1′-ethyl-4H-spiro[1,2,4-benzothiadiazine-3,4′- piperidine] 1,1-dioxide (2) is described in the present work. The synthesized compounds were studied by IR, 1H and 13C NMR, and single crystal X-ray diffraction to determine their molecular and crystal structure. In both structures the conformation of the 1,2,4-thiadiazinane ring is a twisted chair and is stabilized by the intramolecular interaction of the C–H…O type. Compound 1 crystallizes in the monoclinic crystal system and space group C2/c with the unit cell parameters a = 15.8690(17) Å, b = 12.1453(16) Å, c = 12.0152(15) Å, β = 99.686(7)°, Z = 8 and V = 2282.7(5) Å3. Compound 2 crystallizes in the monoclinic crystal system and space group P21/c with the unit cell parameters a = 14.5748(6) Å, b = 9.3340(5) Å, c = 12.4283(6) Å, β = 112.757(2)°, Z = 4 and V = 1559.14(13) Å3. In the crystal structures different packing motifs are implemented with the formation of supramolecular assemblies of different types due to classical hydrogen bonds such as N–H…O and intermolecular interactions of N–H…Br, N–H…N, C–H…O types and π…π stacking.

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Authors and Affiliations

  1. Department of Studies and Research in Chemistry, Tumkur University, Tumkur, India

    P. P. S. Kumar, S. Sreenivasa & D. B. A. Kumar

  2. Department of Chemistry, University College of Science, Tumkur University, Tumkur, India

    P. A. Suchetan

  3. Institution of Excellence, Vijnana Bhavan, University of Mysore, Manasagangotri, India

    S. Naveen

  4. Department of Studies in Physics, University of Mysore, Manasagangotri, India

    N. K. Lokanath

Authors
  1. P. P. S. Kumar
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  2. P. A. Suchetan
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  3. S. Sreenivasa
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  4. S. Naveen
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  5. N. K. Lokanath
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  6. D. B. A. Kumar
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Correspondence to S. Sreenivasa.

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Original Russian Text © 2015 P. P. S. Kumar, P. A. Suchetan, S. Sreenivasa, S. Naveen, N. K. Lokanath, D. B. A. Kumar.

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 56, No. 7, pp. 1449-1456, November-December, 2015.

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Kumar, P.P.S., Suchetan, P.A., Sreenivasa, S. et al. Molecular and crystal structures of two 1,2,4-benzothiadiazine derivatives. J Struct Chem 56, 1390–1397 (2015). https://doi.org/10.1134/S0022476615070215

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  • DOI: https://doi.org/10.1134/S0022476615070215

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