tert-butyl [(4-fluoro-3-isopropoxyisoxazol-5-yl)meth­yl](phenyl­sulfon­yl)carbamate

Mohd Abdul Fatah Abdul Manan; David B. Cordes

doi:10.1107/S2414314625003852

tert-butyl [(4-fluoro-3-isopropoxyisoxazol-5-yl)methyl](phenylsulfonyl)carbamate

Mohd Abdul Fatah Abdul Manan^*, David B. Cordes

^*Corresponding author for this work

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

Abstract

The title compound, C₁₈H₂₃FN₂O₆S, a new derivative of a fluoroisoxazole containing sulfonamide functionality has been structurally characterized. The C—S—N—C_ipr and C—S—N—C_carb (ipr = 3-isopropoxyisoxazole, carb = carbamate) torsion angles are 111.1 (3)° and −70.0 (4)°, respectively. The sulfonamide functional group of this structure features S=O bond lengths of 1.403 (3) and 1.433 (3) Å, an S—N bond length of 1.672 (4) Å, and an S—C bond length of 1.753 (4) Å. The crystal packing features non-classical C—H⋯O hydrogen-bond interactions, with the carbonyl atom acting as a bifurcated acceptor, resulting in an R¹₂(8) ring.

Original language	English
Article number	x250385
Number of pages	3
Journal	IUCrData
Volume	10
Issue number	5
DOIs	https://doi.org/10.1107/S2414314625003852
Publication status	Published - 2 May 2025

Keywords

Crystal structure
Isoxazole
Fluorine
N-fluorobenzenesulfonimide
Sulfonamide
Bifurcated hydrogen bond

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10.1107/S2414314625003852Licence: CC BY

Abdul-Manan_2025_IUCrData_tert-butyl-phenylsulfonyl-carbamate_CC
© The Author(s) 2025. This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence (https://creativecommons.org/licenses/by/4.0/legalcode), which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Final published version, 2.69 MBLicence: CC BY

CCDC 2447656: Experimental Crystal Structure Determination
Manan, M. A. F. A. (Creator) & Cordes, D. B. (Creator), Cambridge Crystallographic Data Centre, 2025
DOI: 10.5517/ccdc.csd.cc2n4zng
Dataset

Cite this

@article{bbde0f3941144308a4abc59114f9897c,

title = "tert-butyl [(4-fluoro-3-isopropoxyisoxazol-5-yl)methyl](phenylsulfonyl)carbamate",

abstract = "The title compound, C18H23FN2O6S, a new derivative of a fluoroisoxazole containing sulfonamide functionality has been structurally characterized. The C—S—N—Cipr and C—S—N—Ccarb (ipr = 3-isopropoxyisoxazole, carb = carbamate) torsion angles are 111.1 (3)° and −70.0 (4)°, respectively. The sulfonamide functional group of this structure features S=O bond lengths of 1.403 (3) and 1.433 (3) {\AA}, an S—N bond length of 1.672 (4) {\AA}, and an S—C bond length of 1.753 (4) {\AA}. The crystal packing features non-classical C—H⋯O hydrogen-bond interactions, with the carbonyl atom acting as a bifurcated acceptor, resulting in an R12(8) ring.",

keywords = "Crystal structure, Isoxazole, Fluorine, N-fluorobenzenesulfonimide, Sulfonamide, Bifurcated hydrogen bond",

author = "{Abdul Manan}, {Mohd Abdul Fatah} and Cordes, {David B.}",

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

year = "2025",

month = may,

day = "2",

doi = "10.1107/S2414314625003852",

language = "English",

volume = "10",

journal = "IUCrData",

issn = "2414-3146",

publisher = "International Union of Crystallography",

number = "5",

}

TY - JOUR

T1 - tert-butyl [(4-fluoro-3-isopropoxyisoxazol-5-yl)methyl](phenylsulfonyl)carbamate

AU - Abdul Manan, Mohd Abdul Fatah

AU - Cordes, David B.

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

PY - 2025/5/2

Y1 - 2025/5/2

N2 - The title compound, C18H23FN2O6S, a new derivative of a fluoroisoxazole containing sulfonamide functionality has been structurally characterized. The C—S—N—Cipr and C—S—N—Ccarb (ipr = 3-isopropoxyisoxazole, carb = carbamate) torsion angles are 111.1 (3)° and −70.0 (4)°, respectively. The sulfonamide functional group of this structure features S=O bond lengths of 1.403 (3) and 1.433 (3) Å, an S—N bond length of 1.672 (4) Å, and an S—C bond length of 1.753 (4) Å. The crystal packing features non-classical C—H⋯O hydrogen-bond interactions, with the carbonyl atom acting as a bifurcated acceptor, resulting in an R12(8) ring.

AB - The title compound, C18H23FN2O6S, a new derivative of a fluoroisoxazole containing sulfonamide functionality has been structurally characterized. The C—S—N—Cipr and C—S—N—Ccarb (ipr = 3-isopropoxyisoxazole, carb = carbamate) torsion angles are 111.1 (3)° and −70.0 (4)°, respectively. The sulfonamide functional group of this structure features S=O bond lengths of 1.403 (3) and 1.433 (3) Å, an S—N bond length of 1.672 (4) Å, and an S—C bond length of 1.753 (4) Å. The crystal packing features non-classical C—H⋯O hydrogen-bond interactions, with the carbonyl atom acting as a bifurcated acceptor, resulting in an R12(8) ring.

KW - Crystal structure

KW - Isoxazole

KW - Fluorine

KW - N-fluorobenzenesulfonimide

KW - Sulfonamide

KW - Bifurcated hydrogen bond

U2 - 10.1107/S2414314625003852

DO - 10.1107/S2414314625003852

M3 - Article

SN - 2414-3146

VL - 10

JO - IUCrData

JF - IUCrData

IS - 5

M1 - x250385

ER -

tert-butyl [(4-fluoro-3-isopropoxyisoxazol-5-yl)meth­yl](phenyl­sulfon­yl)carbamate

Abstract

Keywords

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Datasets

CCDC 2447656: Experimental Crystal Structure Determination

Cite this

tert-butyl [(4-fluoro-3-isopropoxyisoxazol-5-yl)methyl](phenylsulfonyl)carbamate