An X-ray study of the most probable conformers of s-triazolebenzothiazinès inferred from 1H NMR spectra. The structures of 1-(4-nitrophenyl)-3-(4-chlorophenyl)-7,8-dimethoxy-10-methyl-s-triazolobenzothiazine, 1-phenyl-3-(4-chlorophenyl)-7,8-dimethoxy- 10-methyl-s-triazolobenzothiazine and 1-(4-chlorophenyl)-3-carbethoxy-7,8-dimethoxy-10-methyl-s-triazolobenzothiazine

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Abstract

The structures of the title compounds have been established by X-ray crystallography from diffractometry data. Crystals of the first (2c) C2, H21, ClN4O4S · 2H2O are triclinic, space group P1, with a = 9.292(2), b = 11.521(1), c = 12.077 A, a = 102.83(1), β = 95.59(1), γ = 86.98(1), Z = 2, Dc = 1.412 g cm-3. Crystals of the second (2d) C24H22-CIN3O2S are triclinic, space group P1, with a = 8.688(2), b = 10.248(1), c = 13.707(1) A, α = 104.52(1), β = 94.30(1), γ = 65.88(1)°, Z = 2, Dc = 1.393 g cm-3. Crystals of the third (2g) C21H22ClN3O4S are also triclinic, space group P1, with a = 7.344(2), b = 12.186(1), c = 13.440(2) A, α = 76.80(1), β = 78.67(1), γ = 70.87(1)°, Z = 2, Dc = 1.356 g cm-3. The structures, determined by direct methods were refined to R = 0.083 for 3283 reflections of 2c, R = 0.034 for 2590 reflections of 2d and R = 0.044 for 2488 reflections of 2g. The refinement of 2c was limited by the presence of two positionally disordered water molecules. The ambiguities of the interpretation of 1H NMR spectra have been elucidated by these structure determinations underscoring the predominance of the cis junction between the six- and five-membered hetero kings (E/C) and the cis inverse form of the thiazine ring. It was shown, however, that the inversion of N1 is not hindered. The detailed analysis of the three molecular geometries basically substantiated the flexible B and E conformers suggested by Sohár and co-workers (Org. Magn. Reson., 22 (1984) 720).

Original languageEnglish
Pages (from-to)271-286
Number of pages16
JournalJournal of Molecular Structure
Volume129
Issue number3-4
DOIs
Publication statusPublished - 1985

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Thiazines
X Ray Crystallography
Nuclear magnetic resonance
X-Rays
X rays
nuclear magnetic resonance
Crystals
Water
thiazine (trademark)
crystals
x rays
X ray crystallography
ambiguity
crystallography
inversions
Molecules
Geometry
rings
geometry
water

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Materials Science (miscellaneous)
  • Atomic and Molecular Physics, and Optics

Cite this

@article{4fdb1532afe14cc591628c3e30d8a74c,
title = "An X-ray study of the most probable conformers of s-triazolebenzothiazin{\`e}s inferred from 1H NMR spectra. The structures of 1-(4-nitrophenyl)-3-(4-chlorophenyl)-7,8-dimethoxy-10-methyl-s-triazolobenzothiazine, 1-phenyl-3-(4-chlorophenyl)-7,8-dimethoxy- 10-methyl-s-triazolobenzothiazine and 1-(4-chlorophenyl)-3-carbethoxy-7,8-dimethoxy-10-methyl-s-triazolobenzothiazine",
abstract = "The structures of the title compounds have been established by X-ray crystallography from diffractometry data. Crystals of the first (2c) C2, H21, ClN4O4S · 2H2O are triclinic, space group P1, with a = 9.292(2), b = 11.521(1), c = 12.077 A, a = 102.83(1), β = 95.59(1), γ = 86.98(1), Z = 2, Dc = 1.412 g cm-3. Crystals of the second (2d) C24H22-CIN3O2S are triclinic, space group P1, with a = 8.688(2), b = 10.248(1), c = 13.707(1) A, α = 104.52(1), β = 94.30(1), γ = 65.88(1)°, Z = 2, Dc = 1.393 g cm-3. Crystals of the third (2g) C21H22ClN3O4S are also triclinic, space group P1, with a = 7.344(2), b = 12.186(1), c = 13.440(2) A, α = 76.80(1), β = 78.67(1), γ = 70.87(1)°, Z = 2, Dc = 1.356 g cm-3. The structures, determined by direct methods were refined to R = 0.083 for 3283 reflections of 2c, R = 0.034 for 2590 reflections of 2d and R = 0.044 for 2488 reflections of 2g. The refinement of 2c was limited by the presence of two positionally disordered water molecules. The ambiguities of the interpretation of 1H NMR spectra have been elucidated by these structure determinations underscoring the predominance of the cis junction between the six- and five-membered hetero kings (E/C) and the cis inverse form of the thiazine ring. It was shown, however, that the inversion of N1 is not hindered. The detailed analysis of the three molecular geometries basically substantiated the flexible B and E conformers suggested by Soh{\'a}r and co-workers (Org. Magn. Reson., 22 (1984) 720).",
author = "A. K{\'a}lm{\'a}n and G. Argay and P. Soh{\'a}r and L. Fodor and J. Szab{\'o} and G. Bern{\'a}th",
year = "1985",
doi = "10.1016/0022-2860(85)80171-X",
language = "English",
volume = "129",
pages = "271--286",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",
number = "3-4",

}

TY - JOUR

T1 - An X-ray study of the most probable conformers of s-triazolebenzothiazinès inferred from 1H NMR spectra. The structures of 1-(4-nitrophenyl)-3-(4-chlorophenyl)-7,8-dimethoxy-10-methyl-s-triazolobenzothiazine, 1-phenyl-3-(4-chlorophenyl)-7,8-dimethoxy- 10-methyl-s-triazolobenzothiazine and 1-(4-chlorophenyl)-3-carbethoxy-7,8-dimethoxy-10-methyl-s-triazolobenzothiazine

AU - Kálmán, A.

AU - Argay, G.

AU - Sohár, P.

AU - Fodor, L.

AU - Szabó, J.

AU - Bernáth, G.

PY - 1985

Y1 - 1985

N2 - The structures of the title compounds have been established by X-ray crystallography from diffractometry data. Crystals of the first (2c) C2, H21, ClN4O4S · 2H2O are triclinic, space group P1, with a = 9.292(2), b = 11.521(1), c = 12.077 A, a = 102.83(1), β = 95.59(1), γ = 86.98(1), Z = 2, Dc = 1.412 g cm-3. Crystals of the second (2d) C24H22-CIN3O2S are triclinic, space group P1, with a = 8.688(2), b = 10.248(1), c = 13.707(1) A, α = 104.52(1), β = 94.30(1), γ = 65.88(1)°, Z = 2, Dc = 1.393 g cm-3. Crystals of the third (2g) C21H22ClN3O4S are also triclinic, space group P1, with a = 7.344(2), b = 12.186(1), c = 13.440(2) A, α = 76.80(1), β = 78.67(1), γ = 70.87(1)°, Z = 2, Dc = 1.356 g cm-3. The structures, determined by direct methods were refined to R = 0.083 for 3283 reflections of 2c, R = 0.034 for 2590 reflections of 2d and R = 0.044 for 2488 reflections of 2g. The refinement of 2c was limited by the presence of two positionally disordered water molecules. The ambiguities of the interpretation of 1H NMR spectra have been elucidated by these structure determinations underscoring the predominance of the cis junction between the six- and five-membered hetero kings (E/C) and the cis inverse form of the thiazine ring. It was shown, however, that the inversion of N1 is not hindered. The detailed analysis of the three molecular geometries basically substantiated the flexible B and E conformers suggested by Sohár and co-workers (Org. Magn. Reson., 22 (1984) 720).

AB - The structures of the title compounds have been established by X-ray crystallography from diffractometry data. Crystals of the first (2c) C2, H21, ClN4O4S · 2H2O are triclinic, space group P1, with a = 9.292(2), b = 11.521(1), c = 12.077 A, a = 102.83(1), β = 95.59(1), γ = 86.98(1), Z = 2, Dc = 1.412 g cm-3. Crystals of the second (2d) C24H22-CIN3O2S are triclinic, space group P1, with a = 8.688(2), b = 10.248(1), c = 13.707(1) A, α = 104.52(1), β = 94.30(1), γ = 65.88(1)°, Z = 2, Dc = 1.393 g cm-3. Crystals of the third (2g) C21H22ClN3O4S are also triclinic, space group P1, with a = 7.344(2), b = 12.186(1), c = 13.440(2) A, α = 76.80(1), β = 78.67(1), γ = 70.87(1)°, Z = 2, Dc = 1.356 g cm-3. The structures, determined by direct methods were refined to R = 0.083 for 3283 reflections of 2c, R = 0.034 for 2590 reflections of 2d and R = 0.044 for 2488 reflections of 2g. The refinement of 2c was limited by the presence of two positionally disordered water molecules. The ambiguities of the interpretation of 1H NMR spectra have been elucidated by these structure determinations underscoring the predominance of the cis junction between the six- and five-membered hetero kings (E/C) and the cis inverse form of the thiazine ring. It was shown, however, that the inversion of N1 is not hindered. The detailed analysis of the three molecular geometries basically substantiated the flexible B and E conformers suggested by Sohár and co-workers (Org. Magn. Reson., 22 (1984) 720).

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U2 - 10.1016/0022-2860(85)80171-X

DO - 10.1016/0022-2860(85)80171-X

M3 - Article

AN - SCOPUS:33751280188

VL - 129

SP - 271

EP - 286

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

IS - 3-4

ER -