N′-(1,3-Benzo­thia­zol-2-yl) benzene­sulfono­hydrazide

crystal structure, Hirshfeld surface analysis and computational chemistry

Thomas C. Baddeley, Marcus V. N. de Souza, James L. Wardell (Corresponding Author), Mukesh M. Jotani, Edward R. T. Tiekink (Corresponding Author)

Research output: Contribution to journalArticle

Abstract

The asymmetric unit of the title compound, C13H11N3O2S2, comprises two independent mol­ecules (Aand B); the crystal structure was determined by employing synchrotron radiation. The mol­ecules exhibit essentially the same features with an almost planar benzo­thia­zole ring (r.m.s. deviation = 0.026 and 0.009 Å for A and B, respectively), which forms an inclined dihedral angle with the phenyl ring [28.3 (3) and 29.1 (3)°, respectively]. A difference between the mol­ecules is noted in a twist about the N—S bonds [the C—S—N—N torsion angles = −56.2 (5) and −68.8 (5)°, respectively], which leads to a minor difference in orientation of the phenyl rings. In the mol­ecular packing, A and B are linked into a supra­molecular dimer via pairwise hydrazinyl-N—H⋯N(thiazol­yl) hydrogen bonds. Hydrazinyl-N—H⋯O(sulfon­yl) hydrogen bonds between A mol­ecules assemble the dimers into chains along the a-axis direction, while links between centrosymmetrically related B mol­ecules, leading to eight-membered {⋯HNSO}2 synthons, link the mol­ecules along [001]. The result is an undulating supra­molecular layer. Layers stack along the b-axis direction with benzo­thia­zole-C—H⋯O(sulfon­yl) points of contact being evident. The analyses of the calculated Hirshfeld surfaces confirm the relevance of the above inter­molecular inter­actions, but also serve to further differentiate the weaker inter­molecular inter­actions formed by the independent mol­ecules, such as π–π inter­actions. This is also highlighted in distinctive energy frameworks calculated for the individual mol­ecules.

Original languageEnglish
Pages (from-to)516-523
Number of pages8
JournalActa Crystallographica Section E: Crystallographic Communications
Volume75
Issue number4
Early online date29 Mar 2019
DOIs
Publication statusPublished - 1 Apr 2019

Fingerprint

Computational chemistry
computational chemistry
Surface analysis
Crystal structure
chemistry
crystal structure
Molecules
molecules
rings
Hydrogen bonds
hydrogen bonds
Dihedral angle
Synchrotron radiation
Dimers
Torsional stress
torsion
dihedral angle
synchrotron radiation
dimers
interactions

Keywords

  • Hirshfeld surface analysis
  • benzothiazole
  • computational chemistry.
  • crystal structure
  • hydrogen bonding
  • sulfonylhydrazinyl

ASJC Scopus subject areas

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

Cite this

N′-(1,3-Benzo­thia­zol-2-yl) benzene­sulfono­hydrazide : crystal structure, Hirshfeld surface analysis and computational chemistry. / Baddeley, Thomas C.; de Souza, Marcus V. N.; Wardell, James L. (Corresponding Author); Jotani, Mukesh M.; Tiekink, Edward R. T. (Corresponding Author).

In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 75, No. 4, 01.04.2019, p. 516-523.

Research output: Contribution to journalArticle

@article{91781afea67c4ccf8dcd03c32825224b,
title = "N′-(1,3-Benzo­thia­zol-2-yl) benzene­sulfono­hydrazide: crystal structure, Hirshfeld surface analysis and computational chemistry",
abstract = "The asymmetric unit of the title compound, C13H11N3O2S2, comprises two independent mol­ecules (Aand B); the crystal structure was determined by employing synchrotron radiation. The mol­ecules exhibit essentially the same features with an almost planar benzo­thia­zole ring (r.m.s. deviation = 0.026 and 0.009 {\AA} for A and B, respectively), which forms an inclined dihedral angle with the phenyl ring [28.3 (3) and 29.1 (3)°, respectively]. A difference between the mol­ecules is noted in a twist about the N—S bonds [the C—S—N—N torsion angles = −56.2 (5) and −68.8 (5)°, respectively], which leads to a minor difference in orientation of the phenyl rings. In the mol­ecular packing, A and B are linked into a supra­molecular dimer via pairwise hydrazinyl-N—H⋯N(thiazol­yl) hydrogen bonds. Hydrazinyl-N—H⋯O(sulfon­yl) hydrogen bonds between A mol­ecules assemble the dimers into chains along the a-axis direction, while links between centrosymmetrically related B mol­ecules, leading to eight-membered {⋯HNSO}2 synthons, link the mol­ecules along [001]. The result is an undulating supra­molecular layer. Layers stack along the b-axis direction with benzo­thia­zole-C—H⋯O(sulfon­yl) points of contact being evident. The analyses of the calculated Hirshfeld surfaces confirm the relevance of the above inter­molecular inter­actions, but also serve to further differentiate the weaker inter­molecular inter­actions formed by the independent mol­ecules, such as π–π inter­actions. This is also highlighted in distinctive energy frameworks calculated for the individual mol­ecules.",
keywords = "Hirshfeld surface analysis, benzothiazole, computational chemistry., crystal structure, hydrogen bonding, sulfonylhydrazinyl",
author = "Baddeley, {Thomas C.} and {de Souza}, {Marcus V. N.} and Wardell, {James L.} and Jotani, {Mukesh M.} and Tiekink, {Edward R. T.}",
note = "Acknowledgements We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections.",
year = "2019",
month = "4",
day = "1",
doi = "10.1107/S2056989019003980",
language = "English",
volume = "75",
pages = "516--523",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",
number = "4",

}

TY - JOUR

T1 - N′-(1,3-Benzo­thia­zol-2-yl) benzene­sulfono­hydrazide

T2 - crystal structure, Hirshfeld surface analysis and computational chemistry

AU - Baddeley, Thomas C.

AU - de Souza, Marcus V. N.

AU - Wardell, James L.

AU - Jotani, Mukesh M.

AU - Tiekink, Edward R. T.

N1 - Acknowledgements We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections.

PY - 2019/4/1

Y1 - 2019/4/1

N2 - The asymmetric unit of the title compound, C13H11N3O2S2, comprises two independent mol­ecules (Aand B); the crystal structure was determined by employing synchrotron radiation. The mol­ecules exhibit essentially the same features with an almost planar benzo­thia­zole ring (r.m.s. deviation = 0.026 and 0.009 Å for A and B, respectively), which forms an inclined dihedral angle with the phenyl ring [28.3 (3) and 29.1 (3)°, respectively]. A difference between the mol­ecules is noted in a twist about the N—S bonds [the C—S—N—N torsion angles = −56.2 (5) and −68.8 (5)°, respectively], which leads to a minor difference in orientation of the phenyl rings. In the mol­ecular packing, A and B are linked into a supra­molecular dimer via pairwise hydrazinyl-N—H⋯N(thiazol­yl) hydrogen bonds. Hydrazinyl-N—H⋯O(sulfon­yl) hydrogen bonds between A mol­ecules assemble the dimers into chains along the a-axis direction, while links between centrosymmetrically related B mol­ecules, leading to eight-membered {⋯HNSO}2 synthons, link the mol­ecules along [001]. The result is an undulating supra­molecular layer. Layers stack along the b-axis direction with benzo­thia­zole-C—H⋯O(sulfon­yl) points of contact being evident. The analyses of the calculated Hirshfeld surfaces confirm the relevance of the above inter­molecular inter­actions, but also serve to further differentiate the weaker inter­molecular inter­actions formed by the independent mol­ecules, such as π–π inter­actions. This is also highlighted in distinctive energy frameworks calculated for the individual mol­ecules.

AB - The asymmetric unit of the title compound, C13H11N3O2S2, comprises two independent mol­ecules (Aand B); the crystal structure was determined by employing synchrotron radiation. The mol­ecules exhibit essentially the same features with an almost planar benzo­thia­zole ring (r.m.s. deviation = 0.026 and 0.009 Å for A and B, respectively), which forms an inclined dihedral angle with the phenyl ring [28.3 (3) and 29.1 (3)°, respectively]. A difference between the mol­ecules is noted in a twist about the N—S bonds [the C—S—N—N torsion angles = −56.2 (5) and −68.8 (5)°, respectively], which leads to a minor difference in orientation of the phenyl rings. In the mol­ecular packing, A and B are linked into a supra­molecular dimer via pairwise hydrazinyl-N—H⋯N(thiazol­yl) hydrogen bonds. Hydrazinyl-N—H⋯O(sulfon­yl) hydrogen bonds between A mol­ecules assemble the dimers into chains along the a-axis direction, while links between centrosymmetrically related B mol­ecules, leading to eight-membered {⋯HNSO}2 synthons, link the mol­ecules along [001]. The result is an undulating supra­molecular layer. Layers stack along the b-axis direction with benzo­thia­zole-C—H⋯O(sulfon­yl) points of contact being evident. The analyses of the calculated Hirshfeld surfaces confirm the relevance of the above inter­molecular inter­actions, but also serve to further differentiate the weaker inter­molecular inter­actions formed by the independent mol­ecules, such as π–π inter­actions. This is also highlighted in distinctive energy frameworks calculated for the individual mol­ecules.

KW - Hirshfeld surface analysis

KW - benzothiazole

KW - computational chemistry.

KW - crystal structure

KW - hydrogen bonding

KW - sulfonylhydrazinyl

UR - http://www.scopus.com/inward/record.url?scp=85065476702&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/n13benzothiazol2ylbenzenesulfonohydrazide-crystal-structure-hirshfeld-surface-analysis-computational

U2 - 10.1107/S2056989019003980

DO - 10.1107/S2056989019003980

M3 - Article

VL - 75

SP - 516

EP - 523

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

IS - 4

ER -