3-Chloro-1-methyl-4-[2-(3-phenylallylidene)hydrazinylidene]-3, 4-dihydro-1H-2λ6,1-benzothiazine-2,2-dione

Muhammad Shafiq*, M. Nawaz Tahir, William T. A. Harrison, Islam Ullah Khan, Sidra Shafique

*Corresponding author for this work

Research output: Contribution to journalArticle

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Abstract

In the title compound, C18H16ClN3O2S, the dihedral angle between the aromatic rings is 4.81 (2)° and the alkyl chain takes on an extended conformation [N - C - C - C = 179.2 (4)°]. The conformation of the thiazine ring is an envelope, with the S atom displaced by -0.805 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.046 Å). The Cl atom is an axial conformation and is displaced by 1.761 (4) Å from the thiazine ring plane. In the crystal, inversion dimers linked by pairs of C - H⋯O interactions generate R 2 2(20) loops and further C - H⋯O hydrogen bonds link the dimers into (001) sheets. Weak aromatic π-π stacking interactions [centroid-centroid separations = 3.870 (3) and 3.883 (3) Å] are also observed.

Original languageEnglish
Pages (from-to)o165-o165
Number of pages1
JournalActa Crystallographica Section E: Structure Reports Online
Volume69
Issue number2
Early online date4 Jan 2013
DOIs
Publication statusPublished - 1 Feb 2013

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Dione
Thiazines
thiazine (trademark)
Conformations
Dimers
Atoms
centroids
rings
dimers
atoms
Dihedral angle
dihedral angle
Hydrogen bonds
envelopes
interactions
inversions
hydrogen bonds
deviation
Crystals
crystals

ASJC Scopus subject areas

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

Cite this

3-Chloro-1-methyl-4-[2-(3-phenylallylidene)hydrazinylidene]-3, 4-dihydro-1H-2λ6,1-benzothiazine-2,2-dione. / Shafiq, Muhammad; Tahir, M. Nawaz; Harrison, William T. A.; Khan, Islam Ullah; Shafique, Sidra.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 69, No. 2, 01.02.2013, p. o165-o165.

Research output: Contribution to journalArticle

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title = "3-Chloro-1-methyl-4-[2-(3-phenylallylidene)hydrazinylidene]-3, 4-dihydro-1H-2λ6,1-benzothiazine-2,2-dione",
abstract = "In the title compound, C18H16ClN3O2S, the dihedral angle between the aromatic rings is 4.81 (2)° and the alkyl chain takes on an extended conformation [N - C - C - C = 179.2 (4)°]. The conformation of the thiazine ring is an envelope, with the S atom displaced by -0.805 (3) {\AA} from the mean plane of the other five atoms (r.m.s. deviation = 0.046 {\AA}). The Cl atom is an axial conformation and is displaced by 1.761 (4) {\AA} from the thiazine ring plane. In the crystal, inversion dimers linked by pairs of C - H⋯O interactions generate R 2 2(20) loops and further C - H⋯O hydrogen bonds link the dimers into (001) sheets. Weak aromatic π-π stacking interactions [centroid-centroid separations = 3.870 (3) and 3.883 (3) {\AA}] are also observed.",
author = "Muhammad Shafiq and Tahir, {M. Nawaz} and Harrison, {William T. A.} and Khan, {Islam Ullah} and Sidra Shafique",
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AU - Shafiq, Muhammad

AU - Tahir, M. Nawaz

AU - Harrison, William T. A.

AU - Khan, Islam Ullah

AU - Shafique, Sidra

N1 - Acknowledgements MS acknowledges the HEC Pakistan for granting a PhD fellowship.

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N2 - In the title compound, C18H16ClN3O2S, the dihedral angle between the aromatic rings is 4.81 (2)° and the alkyl chain takes on an extended conformation [N - C - C - C = 179.2 (4)°]. The conformation of the thiazine ring is an envelope, with the S atom displaced by -0.805 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.046 Å). The Cl atom is an axial conformation and is displaced by 1.761 (4) Å from the thiazine ring plane. In the crystal, inversion dimers linked by pairs of C - H⋯O interactions generate R 2 2(20) loops and further C - H⋯O hydrogen bonds link the dimers into (001) sheets. Weak aromatic π-π stacking interactions [centroid-centroid separations = 3.870 (3) and 3.883 (3) Å] are also observed.

AB - In the title compound, C18H16ClN3O2S, the dihedral angle between the aromatic rings is 4.81 (2)° and the alkyl chain takes on an extended conformation [N - C - C - C = 179.2 (4)°]. The conformation of the thiazine ring is an envelope, with the S atom displaced by -0.805 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.046 Å). The Cl atom is an axial conformation and is displaced by 1.761 (4) Å from the thiazine ring plane. In the crystal, inversion dimers linked by pairs of C - H⋯O interactions generate R 2 2(20) loops and further C - H⋯O hydrogen bonds link the dimers into (001) sheets. Weak aromatic π-π stacking interactions [centroid-centroid separations = 3.870 (3) and 3.883 (3) Å] are also observed.

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