4-Fluorobenzyl (Z)-2-(2-oxoindolin-3-ylidene) hydrazine-1-carbodithioate

Mohd Abdul Fatah Abdul Manan; David B. Cordes; Aidan P. McKay

doi:10.1107/S2414314624002359

4-Fluorobenzyl (Z)-2-(2-oxoindolin-3-ylidene) hydrazine-1-carbodithioate

Mohd Abdul Fatah Abdul Manan^*, David B. Cordes, Aidan P. McKay

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

The title compound, C₁₆H₁₂FN₃OS, a fluorinated dithiocarbazate imine derivative, was synthesized by the one-pot, multi-component condensation reaction of hydrazine hydrate, carbon disulfide, 4-fluorobenzyl chloride and isatin. The compound demonstrates near-planarity across much of the molecule in the solid state and a Z configuration for the azomethine C N bond. The Z form is further stabilized by the presence of an intramolecular N—H. . .O hydrogen bond. In the extended structure, molecules are linked into dimers by N—H. . .O hydrogen bonds and further connected into chains along either [210] or [100] by weak C—H. . .S and C—H. . .F hydrogen bonds, which further link into corrugated sheets and in combination form the overall three-dimensional network.

Original language	English
Article number	x240235
Journal	IUCrData
Volume	9
Issue number	Pt 3
Early online date	19 Mar 2024
DOIs	https://doi.org/10.1107/S2414314624002359
Publication status	E-pub ahead of print - 19 Mar 2024

Keywords

crystal structure
dithiocarbazate
fluorine
hydrogen bond
isatin
z configuration

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10.1107/S2414314624002359

Manan_2024_4-Flu_IUCrData_CCBY
© 2024 the authors. This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Final published version, 1.49 MBLicence: CC BY

Cite this

@article{af85efca2daf42eab4b77395faea6b24,

title = "4-Fluorobenzyl (Z)-2-(2-oxoindolin-3-ylidene) hydrazine-1-carbodithioate",

abstract = "The title compound, C16H12FN3OS, a fluorinated dithiocarbazate imine derivative, was synthesized by the one-pot, multi-component condensation reaction of hydrazine hydrate, carbon disulfide, 4-fluorobenzyl chloride and isatin. The compound demonstrates near-planarity across much of the molecule in the solid state and a Z configuration for the azomethine C N bond. The Z form is further stabilized by the presence of an intramolecular N—H. . .O hydrogen bond. In the extended structure, molecules are linked into dimers by N—H. . .O hydrogen bonds and further connected into chains along either [210] or [100] by weak C—H. . .S and C—H. . .F hydrogen bonds, which further link into corrugated sheets and in combination form the overall three-dimensional network.",

keywords = "crystal structure, dithiocarbazate, fluorine, hydrogen bond, isatin, z configuration",

author = "Manan, \{Mohd Abdul Fatah Abdul\} and Cordes, \{David B.\} and McKay, \{Aidan P.\}",

note = "Funding: The authors acknowledge Universiti Teknologi MARA for financial support.",

year = "2024",

month = mar,

day = "19",

doi = "10.1107/S2414314624002359",

language = "English",

volume = "9",

journal = "IUCrData",

issn = "2414-3146",

publisher = "International Union of Crystallography",

number = "Pt 3",

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TY - JOUR

T1 - 4-Fluorobenzyl (Z)-2-(2-oxoindolin-3-ylidene) hydrazine-1-carbodithioate

AU - Manan, Mohd Abdul Fatah Abdul

AU - Cordes, David B.

AU - McKay, Aidan P.

N1 - Funding: The authors acknowledge Universiti Teknologi MARA for financial support.

PY - 2024/3/19

Y1 - 2024/3/19

N2 - The title compound, C16H12FN3OS, a fluorinated dithiocarbazate imine derivative, was synthesized by the one-pot, multi-component condensation reaction of hydrazine hydrate, carbon disulfide, 4-fluorobenzyl chloride and isatin. The compound demonstrates near-planarity across much of the molecule in the solid state and a Z configuration for the azomethine C N bond. The Z form is further stabilized by the presence of an intramolecular N—H. . .O hydrogen bond. In the extended structure, molecules are linked into dimers by N—H. . .O hydrogen bonds and further connected into chains along either [210] or [100] by weak C—H. . .S and C—H. . .F hydrogen bonds, which further link into corrugated sheets and in combination form the overall three-dimensional network.

AB - The title compound, C16H12FN3OS, a fluorinated dithiocarbazate imine derivative, was synthesized by the one-pot, multi-component condensation reaction of hydrazine hydrate, carbon disulfide, 4-fluorobenzyl chloride and isatin. The compound demonstrates near-planarity across much of the molecule in the solid state and a Z configuration for the azomethine C N bond. The Z form is further stabilized by the presence of an intramolecular N—H. . .O hydrogen bond. In the extended structure, molecules are linked into dimers by N—H. . .O hydrogen bonds and further connected into chains along either [210] or [100] by weak C—H. . .S and C—H. . .F hydrogen bonds, which further link into corrugated sheets and in combination form the overall three-dimensional network.

KW - crystal structure

KW - dithiocarbazate

KW - fluorine

KW - hydrogen bond

KW - isatin

KW - z configuration

UR - https://www.scopus.com/pages/publications/85189660845

U2 - 10.1107/S2414314624002359

DO - 10.1107/S2414314624002359

M3 - Article

AN - SCOPUS:85189660845

SN - 2414-3146

VL - 9

JO - IUCrData

JF - IUCrData

IS - Pt 3

M1 - x240235

ER -

4-Fluorobenzyl (Z)-2-(2-oxoindolin-3-ylidene) hydrazine-1-carbodithioate

Abstract

Keywords

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CCDC 2339543: Experimental Crystal Structure Determination

Cite this

4-Fluorobenzyl (Z)-2-(2-oxoindolin-3-ylidene) hydrazine-1-carbodithioate

Abstract

Keywords

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Other files and links

Fingerprint

Datasets

CCDC 2339543: Experimental Crystal Structure Determination

Cite this