MOLECULAR AND CRYSTAL STRUCTURES OF TWO 1,2,4-BENZOTHIADIAZINE DERIVATIVES
P. P. S. Kumar, P. A. Suchetan, S. Sreenivasa, S. Naveen, N. K. Lokanath, D. B. A. Kumar
1Department of Studies and Research in Chemistry, Tumkur University, India
nirmaldb@rediffmail.com
2Department of Chemistry, University College of Science, Tumkur University, India
3Institution of Excellence, Vijnana Bhavan, University of Mysore, Manasagangotri, India
4Department of Studies in Physics, University of Mysore, Manasagangotri, India
Keywords: 1,2,4-benzothiadiazines, IR spectroscopy, X-ray analysis, N-H…O hydrogen bonds, N-H…Br interactions, N-H…N interactions, C-H…O interactions, ПЂ…ПЂ stacking, 124-benzothiadiazines, IR spectroscopy, X-ray analysis, NH…O hydrogen bonds, NH…Br interactions, NH…N interactions, CH…O interactions, ПЂ…ПЂ stacking
Abstract
The synthesis of two 1,2,4-benzothiadiazine derivatives, namely, 6-bromo-4 H -spiro[1,2,4-benzothiadiazine-3,1¢-cyclobutane] 1,1-dioxide (1) and 6-bromo-1¢-ethyl-4 H -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 C 2/ c with the unit cell parameters a = 15.8690(17) Å, b = 12.1453(16) Å, c = 12.0152(15) Å, b = 99.686(7)°, Z = 8 and V = 2282.7(5) Å3. Compound 2 crystallizes in the monoclinic crystal system and space group P 21/c with the unit cell parameters a = 14.5748(6) Å, b = 9.3340(5) Å, c = 12.4283(6) Å, b = 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 p…p stacking.
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