Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-yl­­idene]­hydrazinecarbodi­thio­ate

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

doi:10.1107/s2414314624007879

Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate

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, C₁₀H₈BrN₃OS₂, a brominated dithiocarbazate imine derivative, was obtained from the condensation reaction of S-methyldithiocarbazate (SMDTC) and 5-bromoisatin. The essentially planar molecule exhibits a Z configuration, with the dithiocarbazate and 5-bromoisatin fragments located on the same sides of the C=N azomethine bond, which allows for the formation of an intramolecular N—H⋯O_b (b = bromoisatin) hydrogen bond generating an S(6) ring motif. In the crystal, adjacent molecules are linked by pairs of N—H⋯O hydrogen bonds, forming dimers characterized by an R²₂(8) loop motif. In the extended structure, molecules are linked into a three-dimensional network by C—H⋯S and C—H⋯Br hydrogen bonds, C—Br⋯S halogen bonds and aromatic π–π stacking.

Original language	English
Article number	x240787
Number of pages	7
Journal	IUCrData
Volume	9
Issue number	8
DOIs	https://doi.org/10.1107/s2414314624007879
Publication status	Published - 16 Aug 2024

Keywords

Crystal structure
Hydrogen bonding
Halogen bond
Dithiocarbazate
Z configuration
5-bromoIsatin

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Abdul-Manan_2024_IUCrData_Methyl-hydrazinecarbodithioate_CC
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CCDC 2376721: Experimental Crystal Structure Determination
Manan, M.A.F. Abdul (Creator), Cordes, D.B. (Creator) & McKay, A.P. (Creator), Cambridge Crystallographic Data Centre, 2024
DOI: 10.5517/ccdc.csd.cc2ks5fz
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Cite this

@article{2b93647bcec14cac85ada13c57fff06d,

title = "Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate",

abstract = "The title compound, C10H8BrN3OS2, a brominated dithiocarbazate imine derivative, was obtained from the condensation reaction of S-methyldithiocarbazate (SMDTC) and 5-bromoisatin. The essentially planar molecule exhibits a Z configuration, with the dithiocarbazate and 5-bromoisatin fragments located on the same sides of the C=N azomethine bond, which allows for the formation of an intramolecular N—H⋯Ob (b = bromoisatin) hydrogen bond generating an S(6) ring motif. In the crystal, adjacent molecules are linked by pairs of N—H⋯O hydrogen bonds, forming dimers characterized by an R22(8) loop motif. In the extended structure, molecules are linked into a three-dimensional network by C—H⋯S and C—H⋯Br hydrogen bonds, C—Br⋯S halogen bonds and aromatic π–π stacking.",

keywords = "Crystal structure, Hydrogen bonding, Halogen bond, Dithiocarbazate, Z configuration, 5-bromoIsatin",

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

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

year = "2024",

month = aug,

day = "16",

doi = "10.1107/s2414314624007879",

language = "English",

volume = "9",

journal = "IUCrData",

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publisher = "International Union of Crystallography",

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T1 - Methyl 2-[(Z)-5-bromo-2-oxoindolin-3-ylidene]hydrazinecarbodithioate

AU - Abdul Manan, Mohd Abdul Fatah

AU - Cordes, David B.

AU - McKay, Aidan P.

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

PY - 2024/8/16

Y1 - 2024/8/16

N2 - The title compound, C10H8BrN3OS2, a brominated dithiocarbazate imine derivative, was obtained from the condensation reaction of S-methyldithiocarbazate (SMDTC) and 5-bromoisatin. The essentially planar molecule exhibits a Z configuration, with the dithiocarbazate and 5-bromoisatin fragments located on the same sides of the C=N azomethine bond, which allows for the formation of an intramolecular N—H⋯Ob (b = bromoisatin) hydrogen bond generating an S(6) ring motif. In the crystal, adjacent molecules are linked by pairs of N—H⋯O hydrogen bonds, forming dimers characterized by an R22(8) loop motif. In the extended structure, molecules are linked into a three-dimensional network by C—H⋯S and C—H⋯Br hydrogen bonds, C—Br⋯S halogen bonds and aromatic π–π stacking.

AB - The title compound, C10H8BrN3OS2, a brominated dithiocarbazate imine derivative, was obtained from the condensation reaction of S-methyldithiocarbazate (SMDTC) and 5-bromoisatin. The essentially planar molecule exhibits a Z configuration, with the dithiocarbazate and 5-bromoisatin fragments located on the same sides of the C=N azomethine bond, which allows for the formation of an intramolecular N—H⋯Ob (b = bromoisatin) hydrogen bond generating an S(6) ring motif. In the crystal, adjacent molecules are linked by pairs of N—H⋯O hydrogen bonds, forming dimers characterized by an R22(8) loop motif. In the extended structure, molecules are linked into a three-dimensional network by C—H⋯S and C—H⋯Br hydrogen bonds, C—Br⋯S halogen bonds and aromatic π–π stacking.

KW - Crystal structure

KW - Hydrogen bonding

KW - Halogen bond

KW - Dithiocarbazate

KW - Z configuration

KW - 5-bromoIsatin

U2 - 10.1107/s2414314624007879

DO - 10.1107/s2414314624007879

M3 - Article

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VL - 9

JO - IUCrData

JF - IUCrData

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