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

Saeed Ahmad; Muhammad Shafiq; M. Nawaz Tahir; William T. A. Harrison; Islam Ullah Khan

doi:10.1107/S1600536813004443

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

Saeed Ahmad, Muhammad Shafiq^*, M. Nawaz Tahir, William T. A. Harrison, Islam Ullah Khan

^*Corresponding author for this work

Chemistry

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Abstract

In the title compound, C16H13Cl2N3O2S, the dihedral angle between the aromatic rings is 6.62 (2)° and the C=N - N=C torsion angle is 176.2 (4)°. The thiazine ring shows an envelope conformation, with the S atom displaced by 0.633 (6) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.037 Å). The Cl atom is an an axial conformation and is displaced by 2.015 (6) Å from the thiazine ring plane. In the crystal, molecules are linked by C - H⋯O interactions, generating a three-dimensional network. Very weak aromatic π-π stacking interactions [centroid-centroid separations = 3.928 (2) Å] are also observed.

Original language	English
Pages (from-to)	o422-o423
Number of pages	2
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	69
Issue number	3
Early online date	23 Feb 2013
DOIs	https://doi.org/10.1107/S1600536813004443
Publication status	Published - 1 Mar 2013

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10.1107/S1600536813004443Licence: CC BY

3-Chloro-4-[2-(4-chlorobenzylidene)- hydrazinylidene]-1-methyl-3,4-dihydro- 1 H -2 k 6 ,1-benzothiazine-2,2-dione
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@article{2916fda25b10474b8c9ce4d80f45fdd8,

title = "3-Chloro-4-[2-(4-chlorobenzylidene)hydrazinylidene]-1-methyl-3, 4-dihydro-1H-2λ6,1-benzothiazine-2,2-dione",

abstract = "In the title compound, C16H13Cl2N3O2S, the dihedral angle between the aromatic rings is 6.62 (2)° and the C=N - N=C torsion angle is 176.2 (4)°. The thiazine ring shows an envelope conformation, with the S atom displaced by 0.633 (6) {\AA} from the mean plane of the other five atoms (r.m.s. deviation = 0.037 {\AA}). The Cl atom is an an axial conformation and is displaced by 2.015 (6) {\AA} from the thiazine ring plane. In the crystal, molecules are linked by C - H⋯O interactions, generating a three-dimensional network. Very weak aromatic π-π stacking interactions [centroid-centroid separations = 3.928 (2) {\AA}] are also observed.",

author = "Saeed Ahmad and Muhammad Shafiq and Tahir, {M. Nawaz} and Harrison, {William T. A.} and Khan, {Islam Ullah}",

note = "Acknowledgements MS acknowledges the HEC Pakistan for providing a PhD fellowship and the UOS, Sargodha, for X-ray diffraction facility.",

year = "2013",

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doi = "10.1107/S1600536813004443",

language = "English",

volume = "69",

pages = "o422--o423",

journal = "Acta Crystallographica Section E: Structure Reports Online",

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publisher = "International Union of Crystallography",

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TY - JOUR

T1 - 3-Chloro-4-[2-(4-chlorobenzylidene)hydrazinylidene]-1-methyl-3, 4-dihydro-1H-2λ6,1-benzothiazine-2,2-dione

AU - Ahmad, Saeed

AU - Shafiq, Muhammad

AU - Tahir, M. Nawaz

AU - Harrison, William T. A.

AU - Khan, Islam Ullah

N1 - Acknowledgements MS acknowledges the HEC Pakistan for providing a PhD fellowship and the UOS, Sargodha, for X-ray diffraction facility.

PY - 2013/3/1

Y1 - 2013/3/1

N2 - In the title compound, C16H13Cl2N3O2S, the dihedral angle between the aromatic rings is 6.62 (2)° and the C=N - N=C torsion angle is 176.2 (4)°. The thiazine ring shows an envelope conformation, with the S atom displaced by 0.633 (6) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.037 Å). The Cl atom is an an axial conformation and is displaced by 2.015 (6) Å from the thiazine ring plane. In the crystal, molecules are linked by C - H⋯O interactions, generating a three-dimensional network. Very weak aromatic π-π stacking interactions [centroid-centroid separations = 3.928 (2) Å] are also observed.

AB - In the title compound, C16H13Cl2N3O2S, the dihedral angle between the aromatic rings is 6.62 (2)° and the C=N - N=C torsion angle is 176.2 (4)°. The thiazine ring shows an envelope conformation, with the S atom displaced by 0.633 (6) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.037 Å). The Cl atom is an an axial conformation and is displaced by 2.015 (6) Å from the thiazine ring plane. In the crystal, molecules are linked by C - H⋯O interactions, generating a three-dimensional network. Very weak aromatic π-π stacking interactions [centroid-centroid separations = 3.928 (2) Å] are also observed.

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U2 - 10.1107/S1600536813004443

DO - 10.1107/S1600536813004443

M3 - Article

AN - SCOPUS:84874885044

VL - 69

SP - o422-o423

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

SN - 1600-5368

IS - 3

ER -

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

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