Crystal structures of two isomeric 2-aryl-3-phenyl-1,3-thiazepan-4-ones

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Abstract

The crystal of 6-(3-nitrophenyl)-7-phenyl-5-thia-7-azaspiro[2.6]nonan-8-one (1), C19H18N2O3S, has monoclinic (P21/n) symmetry while that of its isomer 6-(4-nitrophenyl)-7-phenyl-5-thia-7-azaspiro[2.6]nonan-8-one (2), has orthorhombic (Pca21) symmetry: compound 1 has two molecules, A and B, in the asymmetric unit while 2 has one. In all three molecules, the seven-membered thiazepan ring exhibits a chair conformation with Q2 and Q3 values (Å) of 0.521 (3), 0.735 (3) and 0.485 (3), 0.749 (3) in 1 and 0.517 (5), 0.699 (5) in 2. In each structure, the phenyl rings attached to adjacent atoms of the thiazepan ring have interplanar angles ranging between 41 and 47∘. Except for the nitro groups, the three molecules have similar conformations when overlayed in pairs. Both crystal structures are consolidated by C-H∙ ∙ ∙O hydrogen bonds.

Original languageEnglish (US)
Pages (from-to)1270-1276
Number of pages7
JournalActa Crystallographica Section E: Crystallographic Communications
Volume75
DOIs
StatePublished - Jan 1 2019

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Crystal structure
crystal structure
Molecules
Conformations
rings
molecules
symmetry
Isomers
seats
Hydrogen bonds
isomers
hydrogen bonds
Atoms
Crystals
crystals
atoms
4-nitrophenyl

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

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title = "Crystal structures of two isomeric 2-aryl-3-phenyl-1,3-thiazepan-4-ones",
abstract = "The crystal of 6-(3-nitrophenyl)-7-phenyl-5-thia-7-azaspiro[2.6]nonan-8-one (1), C19H18N2O3S, has monoclinic (P21/n) symmetry while that of its isomer 6-(4-nitrophenyl)-7-phenyl-5-thia-7-azaspiro[2.6]nonan-8-one (2), has orthorhombic (Pca21) symmetry: compound 1 has two molecules, A and B, in the asymmetric unit while 2 has one. In all three molecules, the seven-membered thiazepan ring exhibits a chair conformation with Q2 and Q3 values ({\AA}) of 0.521 (3), 0.735 (3) and 0.485 (3), 0.749 (3) in 1 and 0.517 (5), 0.699 (5) in 2. In each structure, the phenyl rings attached to adjacent atoms of the thiazepan ring have interplanar angles ranging between 41 and 47∘. Except for the nitro groups, the three molecules have similar conformations when overlayed in pairs. Both crystal structures are consolidated by C-H∙ ∙ ∙O hydrogen bonds.",
author = "Yennawar, {Hemant P.} and Peterson, {Samuel D.} and Silverberg, {Lee Jonathan}",
year = "2019",
month = "1",
day = "1",
doi = "10.1107/S2056989019010429",
language = "English (US)",
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T1 - Crystal structures of two isomeric 2-aryl-3-phenyl-1,3-thiazepan-4-ones

AU - Yennawar, Hemant P.

AU - Peterson, Samuel D.

AU - Silverberg, Lee Jonathan

PY - 2019/1/1

Y1 - 2019/1/1

N2 - The crystal of 6-(3-nitrophenyl)-7-phenyl-5-thia-7-azaspiro[2.6]nonan-8-one (1), C19H18N2O3S, has monoclinic (P21/n) symmetry while that of its isomer 6-(4-nitrophenyl)-7-phenyl-5-thia-7-azaspiro[2.6]nonan-8-one (2), has orthorhombic (Pca21) symmetry: compound 1 has two molecules, A and B, in the asymmetric unit while 2 has one. In all three molecules, the seven-membered thiazepan ring exhibits a chair conformation with Q2 and Q3 values (Å) of 0.521 (3), 0.735 (3) and 0.485 (3), 0.749 (3) in 1 and 0.517 (5), 0.699 (5) in 2. In each structure, the phenyl rings attached to adjacent atoms of the thiazepan ring have interplanar angles ranging between 41 and 47∘. Except for the nitro groups, the three molecules have similar conformations when overlayed in pairs. Both crystal structures are consolidated by C-H∙ ∙ ∙O hydrogen bonds.

AB - The crystal of 6-(3-nitrophenyl)-7-phenyl-5-thia-7-azaspiro[2.6]nonan-8-one (1), C19H18N2O3S, has monoclinic (P21/n) symmetry while that of its isomer 6-(4-nitrophenyl)-7-phenyl-5-thia-7-azaspiro[2.6]nonan-8-one (2), has orthorhombic (Pca21) symmetry: compound 1 has two molecules, A and B, in the asymmetric unit while 2 has one. In all three molecules, the seven-membered thiazepan ring exhibits a chair conformation with Q2 and Q3 values (Å) of 0.521 (3), 0.735 (3) and 0.485 (3), 0.749 (3) in 1 and 0.517 (5), 0.699 (5) in 2. In each structure, the phenyl rings attached to adjacent atoms of the thiazepan ring have interplanar angles ranging between 41 and 47∘. Except for the nitro groups, the three molecules have similar conformations when overlayed in pairs. Both crystal structures are consolidated by C-H∙ ∙ ∙O hydrogen bonds.

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