Crystal structures of two 2,3-diaryl-2,3-dihydro-4H-1,3-benzothiazin-4-ones

Hemant P. Yennawar, Michaela J. Buchwalter, Baylee K. Colburn, Lee Jonathan Silverberg

Research output: Contribution to journalArticle

Abstract

The syntheses and crystal structures of 2,3-bis[3-(trifluoromethyl)phenyl]-2,3-dihydro-4H-1,3-benzothiazin-4-one (di-m-CF3; C22H13F6NOS) (1) and 2,3-bis(4-methylphenyl)-2,3-dihydro-4H-1,3-benzothiazin-4-one (di-p-CH3; C22H19NOS) (2) are reported. Each structure is racemic: the asymmetric unit of 2 consists of two molecules. In both 1 and 2, the six-membered 1,3-thiazine ring is close to an envelope conformation with the chiral C atom forming the flap. In 1, the 2-aryl group is pseudo-equatorial, while in 2 it is pseudo-axial. In 1, the pendant aryl rings form a V shape with an inter-centroid distance of 3.938 (3) A and an acute dihedral angle of 48.3 (2)° between them. Both CF3 groups are disordered over two orientations in 0.687 (19):0.313 (19) and 0.667 (16):0.33 (16) ratios. In each of the independent molecules of 2, the aryl rings are almost orthogonal to each other [dihedral angles = 85.50 (12) and 86.07 (11)°]. In both structures, the chiral C atom and the O atoms participate in C - H. . .O-type hydrogen bonding between symmetry-related molecules of 1 or the independent enantiomers in 2, forming chains along the c-axis direction in 1 and the b-axis direction in 2. Additionally, in 1, π-π contacts of both face-to-face and edge-to-face type, as well as π-H. . .O and π-H. . .F interactions are observed. In 2, a racemic mixture of molecules forms layers in the ac plane linked by weak π-π and C - H. . .π interactions.

Original languageEnglish (US)
Pages (from-to)363-366
Number of pages4
JournalActa Crystallographica Section E: Crystallographic Communications
Volume74
DOIs
StatePublished - Jan 1 2018

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Crystal structure
crystal structure
Molecules
Dihedral angle
Atoms
dihedral angle
molecules
rings
Thiazines
thiazine (trademark)
atoms
Enantiomers
enantiomers
centroids
Conformations
Hydrogen bonds
envelopes
interactions
symmetry
hydrogen

All Science Journal Classification (ASJC) codes

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

Cite this

@article{5d6ec1711c224ad5b41b2facce52fc7e,
title = "Crystal structures of two 2,3-diaryl-2,3-dihydro-4H-1,3-benzothiazin-4-ones",
abstract = "The syntheses and crystal structures of 2,3-bis[3-(trifluoromethyl)phenyl]-2,3-dihydro-4H-1,3-benzothiazin-4-one (di-m-CF3; C22H13F6NOS) (1) and 2,3-bis(4-methylphenyl)-2,3-dihydro-4H-1,3-benzothiazin-4-one (di-p-CH3; C22H19NOS) (2) are reported. Each structure is racemic: the asymmetric unit of 2 consists of two molecules. In both 1 and 2, the six-membered 1,3-thiazine ring is close to an envelope conformation with the chiral C atom forming the flap. In 1, the 2-aryl group is pseudo-equatorial, while in 2 it is pseudo-axial. In 1, the pendant aryl rings form a V shape with an inter-centroid distance of 3.938 (3) A and an acute dihedral angle of 48.3 (2)° between them. Both CF3 groups are disordered over two orientations in 0.687 (19):0.313 (19) and 0.667 (16):0.33 (16) ratios. In each of the independent molecules of 2, the aryl rings are almost orthogonal to each other [dihedral angles = 85.50 (12) and 86.07 (11)°]. In both structures, the chiral C atom and the O atoms participate in C - H. . .O-type hydrogen bonding between symmetry-related molecules of 1 or the independent enantiomers in 2, forming chains along the c-axis direction in 1 and the b-axis direction in 2. Additionally, in 1, π-π contacts of both face-to-face and edge-to-face type, as well as π-H. . .O and π-H. . .F interactions are observed. In 2, a racemic mixture of molecules forms layers in the ac plane linked by weak π-π and C - H. . .π interactions.",
author = "Yennawar, {Hemant P.} and Buchwalter, {Michaela J.} and Colburn, {Baylee K.} and Silverberg, {Lee Jonathan}",
year = "2018",
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language = "English (US)",
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Crystal structures of two 2,3-diaryl-2,3-dihydro-4H-1,3-benzothiazin-4-ones. / Yennawar, Hemant P.; Buchwalter, Michaela J.; Colburn, Baylee K.; Silverberg, Lee Jonathan.

In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 74, 01.01.2018, p. 363-366.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Crystal structures of two 2,3-diaryl-2,3-dihydro-4H-1,3-benzothiazin-4-ones

AU - Yennawar, Hemant P.

AU - Buchwalter, Michaela J.

AU - Colburn, Baylee K.

AU - Silverberg, Lee Jonathan

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N2 - The syntheses and crystal structures of 2,3-bis[3-(trifluoromethyl)phenyl]-2,3-dihydro-4H-1,3-benzothiazin-4-one (di-m-CF3; C22H13F6NOS) (1) and 2,3-bis(4-methylphenyl)-2,3-dihydro-4H-1,3-benzothiazin-4-one (di-p-CH3; C22H19NOS) (2) are reported. Each structure is racemic: the asymmetric unit of 2 consists of two molecules. In both 1 and 2, the six-membered 1,3-thiazine ring is close to an envelope conformation with the chiral C atom forming the flap. In 1, the 2-aryl group is pseudo-equatorial, while in 2 it is pseudo-axial. In 1, the pendant aryl rings form a V shape with an inter-centroid distance of 3.938 (3) A and an acute dihedral angle of 48.3 (2)° between them. Both CF3 groups are disordered over two orientations in 0.687 (19):0.313 (19) and 0.667 (16):0.33 (16) ratios. In each of the independent molecules of 2, the aryl rings are almost orthogonal to each other [dihedral angles = 85.50 (12) and 86.07 (11)°]. In both structures, the chiral C atom and the O atoms participate in C - H. . .O-type hydrogen bonding between symmetry-related molecules of 1 or the independent enantiomers in 2, forming chains along the c-axis direction in 1 and the b-axis direction in 2. Additionally, in 1, π-π contacts of both face-to-face and edge-to-face type, as well as π-H. . .O and π-H. . .F interactions are observed. In 2, a racemic mixture of molecules forms layers in the ac plane linked by weak π-π and C - H. . .π interactions.

AB - The syntheses and crystal structures of 2,3-bis[3-(trifluoromethyl)phenyl]-2,3-dihydro-4H-1,3-benzothiazin-4-one (di-m-CF3; C22H13F6NOS) (1) and 2,3-bis(4-methylphenyl)-2,3-dihydro-4H-1,3-benzothiazin-4-one (di-p-CH3; C22H19NOS) (2) are reported. Each structure is racemic: the asymmetric unit of 2 consists of two molecules. In both 1 and 2, the six-membered 1,3-thiazine ring is close to an envelope conformation with the chiral C atom forming the flap. In 1, the 2-aryl group is pseudo-equatorial, while in 2 it is pseudo-axial. In 1, the pendant aryl rings form a V shape with an inter-centroid distance of 3.938 (3) A and an acute dihedral angle of 48.3 (2)° between them. Both CF3 groups are disordered over two orientations in 0.687 (19):0.313 (19) and 0.667 (16):0.33 (16) ratios. In each of the independent molecules of 2, the aryl rings are almost orthogonal to each other [dihedral angles = 85.50 (12) and 86.07 (11)°]. In both structures, the chiral C atom and the O atoms participate in C - H. . .O-type hydrogen bonding between symmetry-related molecules of 1 or the independent enantiomers in 2, forming chains along the c-axis direction in 1 and the b-axis direction in 2. Additionally, in 1, π-π contacts of both face-to-face and edge-to-face type, as well as π-H. . .O and π-H. . .F interactions are observed. In 2, a racemic mixture of molecules forms layers in the ac plane linked by weak π-π and C - H. . .π interactions.

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