The X-ray structures of 2- and 3-sulfolene and two halogenated derivatives

R Alan Aitken; Alexandra M.Z. Slawin; Dheirya K. Sonecha

doi:10.1007/s10870-023-00982-4

The X-ray structures of 2- and 3-sulfolene and two halogenated derivatives

R Alan Aitken^*, Alexandra M.Z. Slawin, Dheirya K. Sonecha

^*Corresponding author for this work

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

Abstract

The structures of the isomeric 2,5-dihydrothiophene 1,1-dioxide [orthorhombic, a = 11.340(2), b = 7.0887(15), c = 6.2811(13) Å, space group Pnma] and 2,3-dihydrothiophene 1,1-dioxide [orthorhombic, a = 6.3903(13), b = 7.2783(16), c = 11.075(2) Å, space group Pnma] have been determined and show perfectly planar rings with the expected bond lengths and angles. In contrast, the halogenated derivatives 3,3,4,4-tetrachlorotetrahydrothiophene 1,1-dioxide [monoclinic, a = 11.8716(8), b = 6.5579(4), c = 11.4802(8) Å, β = 97.705(17), space group P2₁/c] and 2,3-dibromotetrahydrothiophene 1,1-dioxide [orthorhombic, a = 5.2502(3), b = 11.3561(6), c = 24.9802(17) Å, space group Pbca] both show twisted conformations. The degree of planarity is compared with that in the structures of comparable 5-membered ring cyclic sulfones and C–H…O hydrogen bonding patterns are discussed for all four structures.

Original language	English
Pages (from-to)	431-437
Number of pages	7
Journal	Journal of Chemical Crystallography
Volume	53
Issue number	3
Early online date	29 Mar 2023
DOIs	https://doi.org/10.1007/s10870-023-00982-4
Publication status	Published - 1 Sept 2023

Keywords

Cyclic sulfones
X-ray structure
Conformation

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CCDC 2225717 - 2225720: Experimental Crystal Structure Determination
Aitken, R. A. (Creator), Slawin, A. M. Z. (Creator) & Sonecha, D. K. (Creator), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2dq1bj, https://dx.doi.org/10.5517/ccdc.csd.cc2dq1fm and 2 more links, https://dx.doi.org/10.5517/ccdc.csd.cc2dq1ck, https://dx.doi.org/10.5517/ccdc.csd.cc2dq1hp (show fewer)
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@article{fba27df8351c4e478db52f7587b0cbfd,

title = "The X-ray structures of 2- and 3-sulfolene and two halogenated derivatives",

abstract = "The structures of the isomeric 2,5-dihydrothiophene 1,1-dioxide [orthorhombic, a = 11.340(2), b = 7.0887(15), c = 6.2811(13) {\AA}, space group Pnma] and 2,3-dihydrothiophene 1,1-dioxide [orthorhombic, a = 6.3903(13), b = 7.2783(16), c = 11.075(2) {\AA}, space group Pnma] have been determined and show perfectly planar rings with the expected bond lengths and angles. In contrast, the halogenated derivatives 3,3,4,4-tetrachlorotetrahydrothiophene 1,1-dioxide [monoclinic, a = 11.8716(8), b = 6.5579(4), c = 11.4802(8) {\AA}, β = 97.705(17), space group P21/c] and 2,3-dibromotetrahydrothiophene 1,1-dioxide [orthorhombic, a = 5.2502(3), b = 11.3561(6), c = 24.9802(17) {\AA}, space group Pbca] both show twisted conformations. The degree of planarity is compared with that in the structures of comparable 5-membered ring cyclic sulfones and C–H…O hydrogen bonding patterns are discussed for all four structures.",

keywords = "Cyclic sulfones, X-ray structure, Conformation",

author = "Aitken, {R Alan} and Slawin, {Alexandra M.Z.} and Sonecha, {Dheirya K.}",

year = "2023",

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doi = "10.1007/s10870-023-00982-4",

language = "English",

volume = "53",

pages = "431--437",

journal = "Journal of Chemical Crystallography",

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TY - JOUR

T1 - The X-ray structures of 2- and 3-sulfolene and two halogenated derivatives

AU - Aitken, R Alan

AU - Slawin, Alexandra M.Z.

AU - Sonecha, Dheirya K.

PY - 2023/9/1

Y1 - 2023/9/1

N2 - The structures of the isomeric 2,5-dihydrothiophene 1,1-dioxide [orthorhombic, a = 11.340(2), b = 7.0887(15), c = 6.2811(13) Å, space group Pnma] and 2,3-dihydrothiophene 1,1-dioxide [orthorhombic, a = 6.3903(13), b = 7.2783(16), c = 11.075(2) Å, space group Pnma] have been determined and show perfectly planar rings with the expected bond lengths and angles. In contrast, the halogenated derivatives 3,3,4,4-tetrachlorotetrahydrothiophene 1,1-dioxide [monoclinic, a = 11.8716(8), b = 6.5579(4), c = 11.4802(8) Å, β = 97.705(17), space group P21/c] and 2,3-dibromotetrahydrothiophene 1,1-dioxide [orthorhombic, a = 5.2502(3), b = 11.3561(6), c = 24.9802(17) Å, space group Pbca] both show twisted conformations. The degree of planarity is compared with that in the structures of comparable 5-membered ring cyclic sulfones and C–H…O hydrogen bonding patterns are discussed for all four structures.

AB - The structures of the isomeric 2,5-dihydrothiophene 1,1-dioxide [orthorhombic, a = 11.340(2), b = 7.0887(15), c = 6.2811(13) Å, space group Pnma] and 2,3-dihydrothiophene 1,1-dioxide [orthorhombic, a = 6.3903(13), b = 7.2783(16), c = 11.075(2) Å, space group Pnma] have been determined and show perfectly planar rings with the expected bond lengths and angles. In contrast, the halogenated derivatives 3,3,4,4-tetrachlorotetrahydrothiophene 1,1-dioxide [monoclinic, a = 11.8716(8), b = 6.5579(4), c = 11.4802(8) Å, β = 97.705(17), space group P21/c] and 2,3-dibromotetrahydrothiophene 1,1-dioxide [orthorhombic, a = 5.2502(3), b = 11.3561(6), c = 24.9802(17) Å, space group Pbca] both show twisted conformations. The degree of planarity is compared with that in the structures of comparable 5-membered ring cyclic sulfones and C–H…O hydrogen bonding patterns are discussed for all four structures.

KW - Cyclic sulfones

KW - X-ray structure

KW - Conformation

U2 - 10.1007/s10870-023-00982-4

DO - 10.1007/s10870-023-00982-4

M3 - Article

SN - 1074-1542

VL - 53

SP - 431

EP - 437

JO - Journal of Chemical Crystallography

JF - Journal of Chemical Crystallography

IS - 3

ER -

The X-ray structures of 2- and 3-sulfolene and two halogenated derivatives

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Datasets

CCDC 2225717 - 2225720: Experimental Crystal Structure Determination

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