2-fluoro­benzyl (Z)-2-(5-chloro-2-oxoindolin-3-yl­­idene)hydrazine-1-carbodi­thio­ate di­methyl sulfoxide monosolvate

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

doi:10.1107/S2414314625008491

2-fluorobenzyl (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate dimethyl sulfoxide monosolvate

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

^*Corresponding author for this work

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

Abstract

In the title solvate, C₁₆H₁₁ClFN₃OS₂·C₂H₆OS, the C=N bond adopts a Z-configuration facilitating the formation of an intramolecular N—H⋯O hydrogen bond to the carbonyl O atom in an S(6) loop. The dimethylsulfoxide solvent molecule accepts a strong discrete N—H⋯O hydrogen bond from the γ-lactam grouping. In the extended structure, C_ar—H⋯S hydrogen bonds and quasi-Type I/II Cl⋯F halogen⋯halogen bonds are observed, while adjacent dimethyl sulfoxide molecules form S⋯O chalcogen-bonded chains.

Original language	English
Article number	x250849
Number of pages	9
Journal	IUCrData
Volume	10
Issue number	10
DOIs	https://doi.org/10.1107/S2414314625008491
Publication status	Published - 1 Oct 2025

Keywords

Crystal structure
Hydrogen bonding
Halogen bonding
Chalcogen bonding

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McKay_2025_IUCrData_2-fluorobenzyl-sufloxide-monosolvate_CC
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Cite this

@article{83028875b4a649629e10bd42023d5479,

title = "2-fluorobenzyl (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate dimethyl sulfoxide monosolvate",

abstract = "In the title solvate, C16H11ClFN3OS2·C2H6OS, the C=N bond adopts a Z-configuration facilitating the formation of an intramolecular N—H⋯O hydrogen bond to the carbonyl O atom in an S(6) loop. The dimethylsulfoxide solvent molecule accepts a strong discrete N—H⋯O hydrogen bond from the γ-lactam grouping. In the extended structure, Car—H⋯S hydrogen bonds and quasi-Type I/II Cl⋯F halogen⋯halogen bonds are observed, while adjacent dimethyl sulfoxide molecules form S⋯O chalcogen-bonded chains.",

keywords = "Crystal structure, Hydrogen bonding, Halogen bonding, Chalcogen bonding",

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

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

year = "2025",

month = oct,

day = "1",

doi = "10.1107/S2414314625008491",

language = "English",

volume = "10",

journal = "IUCrData",

issn = "2414-3146",

publisher = "International Union of Crystallography",

number = "10",

}

TY - JOUR

T1 - 2-fluorobenzyl (Z)-2-(5-chloro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate dimethyl sulfoxide monosolvate

AU - McKay, Aidan P.

AU - Cordes, David B.

AU - Fatah Abdul Manan, Mohd Abdul

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

PY - 2025/10/1

Y1 - 2025/10/1

N2 - In the title solvate, C16H11ClFN3OS2·C2H6OS, the C=N bond adopts a Z-configuration facilitating the formation of an intramolecular N—H⋯O hydrogen bond to the carbonyl O atom in an S(6) loop. The dimethylsulfoxide solvent molecule accepts a strong discrete N—H⋯O hydrogen bond from the γ-lactam grouping. In the extended structure, Car—H⋯S hydrogen bonds and quasi-Type I/II Cl⋯F halogen⋯halogen bonds are observed, while adjacent dimethyl sulfoxide molecules form S⋯O chalcogen-bonded chains.

AB - In the title solvate, C16H11ClFN3OS2·C2H6OS, the C=N bond adopts a Z-configuration facilitating the formation of an intramolecular N—H⋯O hydrogen bond to the carbonyl O atom in an S(6) loop. The dimethylsulfoxide solvent molecule accepts a strong discrete N—H⋯O hydrogen bond from the γ-lactam grouping. In the extended structure, Car—H⋯S hydrogen bonds and quasi-Type I/II Cl⋯F halogen⋯halogen bonds are observed, while adjacent dimethyl sulfoxide molecules form S⋯O chalcogen-bonded chains.

KW - Crystal structure

KW - Hydrogen bonding

KW - Halogen bonding

KW - Chalcogen bonding

U2 - 10.1107/S2414314625008491

DO - 10.1107/S2414314625008491

M3 - Article

SN - 2414-3146

VL - 10

JO - IUCrData

JF - IUCrData

IS - 10

M1 - x250849

ER -