The X-ray Structures of 2- and 3-Sulfolene and Two Halogenated Derivatives

IF 0.4 4区化学 Q4 CRYSTALLOGRAPHY Journal of Chemical Crystallography Pub Date : 2023-03-29 DOI:10.1007/s10870-023-00982-4

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

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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.

Graphical Abstract

The two isomeric sulfolenes are perfectly planar while tetrachloro- and dibromo-derivatives adopt twisted structures.

Abstract Image

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2-和3-亚砜及其两种卤化衍生物的x射线结构

确定了2,5-二氢噻吩1,1-二氧化二异构体[正交，a = 11.340(2)， b = 7.0887(15)， c = 6.2811(13) Å，空间群Pnma]和2,3-二氢噻吩1,1-二氧化二异构体[正交，a = 6.3903(13)， b = 7.2783(16)， c = 11.075(2) Å，空间群Pnma]的结构，并显示出符合预期键长和键角的完美平面环。而卤代衍生物3,3,4,4-四氯四氢噻吩1,1- 2[单斜晶，a = 11.8716(8)， b = 6.5579(4)， c = 11.4802(8) Å， β = 97.705(17)，空间群P21/c]和2,3-二溴四氢噻吩1,1- 2[正交晶，a = 5.2502(3)， b = 11.3561(6)， c = 24.9802(17) Å，空间群Pbca]均表现为扭曲构象。与同类5元环砜结构的平面度进行了比较，并讨论了这四种结构的C-H…O氢键模式。两种同分异构体亚砜是完美的平面结构，而四氯衍生物和二溴衍生物则是扭曲结构。

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来源期刊

Journal of Chemical Crystallography 化学-光谱学

CiteScore

1.50

自引率

12.50%

发文量

审稿时长

6.3 months

期刊介绍： Journal of Chemical Crystallography is an international and interdisciplinary publication dedicated to the rapid dissemination of research results in the general areas of crystallography and spectroscopy. Timely research reports detail topics in crystal chemistry and physics and their relation to problems of molecular structure; structural studies of solids, liquids, gases, and solutions involving spectroscopic, spectrometric, X-ray, and electron and neutron diffraction; and theoretical studies.