Crystal structure determination as part of an ongoing undergraduate organic laboratory project: 5-[(<i>E</i>)-styryl]-1,3,4-oxathiazol-2-one

Nason, Trevor R.; Schriver, Melbourne J.; Hendsbee, Arthur D.; Masuda, Jason D.

doi:10.1107/s2056989017011264

Cited by 3 publications

(11 citation statements)

References 16 publications

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“…The bond distances and angles within the oxathiazolone rings in compounds (I) and (II) are not significantly different ( ! 3) from the statistical averages for published crystal structures (Schriver & Zaworotko, 1995;Bridson et al 1994Bridson et al , 1995Vorontsova et al, 1996;McMillan et al, 2006;Krayushkin et al, 2010a,b;Nason et al, 2017). The sum of the endocyclic bond angles in the oxathiazolone rings for both (I) and (II) (540.0 ) is consistent with planar rings (ideal sum = 540 ).…”

Section: Figurementioning

confidence: 75%

“…Taken together, the contacts between two pairs of identical molecules in the asymmetric unit form a centrosymmetric tetramer that in turn form -stacks parallel to the a axis. The intermolecular contacts between sulfur and nitrogen and oxygen have been observed in another oxathiazolone ring that also resulted in -stacking of the planar molecules (Nason et al, 2017).…”

Section: Supramolecular Featuresmentioning

confidence: 96%

“…-stacking in the styryl derivative (Nason et al, 2017). The strongest intermolecular contacts in (Fig.…”

Section: Supramolecular Featuresmentioning

confidence: 99%

“…A search of the Cambridge Structural Database (Version 5.38; Groom et al, 2016) revealed that eleven crystal structures of oxathiazolone derivatives in peer-reviewed journals have been reported previously (Bridson et al, 1994(Bridson et al, , 1995Schriver & Zaworotko, 1995;Vorontsova et al, 1996;McMillan et al, 2006;Krayushkin et al, 2010a,b;Nason et al, 2017), which have been partially reviewed (McMillan et al, 2006 andKrayushkin et al, 2010a,b). An additional five X-ray oxathiazolone crystal structures have been reported in theses (Demas, 1982;Zhu, 1997).…”

Section: Database Surveymentioning

confidence: 99%

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The crystal structures of two isomers of 5-(phenylisothiazolyl)-1,3,4-oxathiazol-2-one

et al. 2017

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The syntheses and crystal structures of two isomers of phenyl isothiazolyl oxathiazolone, C 11 H 6 N 2 O 2 S 2 , are described [systematic names: 5-(3-phenylisothiazol-5-yl)-1,3,4-oxathiazol-2-one, (I), and 5-(3-phenylisothiazol-4-yl)-1,3,4-oxathiazol-2-one, (II)]. There are two almost planar (r.m.s. deviations = 0.032 and 0.063 Å ) molecules of isomer (I) in the asymmetric unit, which form centrosymmetric tetramers linked by strong SÁ Á ÁN [3.072 (2) Å ] and SÁ Á ÁO contacts [3.089 (1) Å ]. The tetramers are -stacked parallel to the a-axis direction. The single molecule in the asymmetric unit of isomer (II) is twisted into a non-planar conformation by steric repulsion [dihedral angles between the central isothiazolyl ring and the pendant oxathiazolone and phenyl rings are 13.27 (6) and 61.18 (7) , respectively], which disrupts the -conjugation between the heteroaromatic isothiazoloyl ring and the non-aromatic oxathiazolone heterocycle. In the crystal of isomer (II), the strong SÁ Á ÁO [3.020 (1) Å ] and SÁ Á ÁC contacts [3.299 (2) Å ] and the non-planar structure of the molecule lead to a form of -stacking not observed in isomer (I) or other oxathiazolone derivatives.

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Section: Figurementioning

confidence: 75%

Section: Supramolecular Featuresmentioning

confidence: 96%

“…-stacking in the styryl derivative (Nason et al, 2017). The strongest intermolecular contacts in (Fig.…”

Section: Supramolecular Featuresmentioning

confidence: 99%

Section: Database Surveymentioning

confidence: 99%

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The crystal structures of two isomers of 5-(phenylisothiazolyl)-1,3,4-oxathiazol-2-one

et al. 2017

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“…The incorporation of the preparation, isolation and structural characterization of heterocyclic compounds to demonstrate the chemistry of carboxylic acid derivatives in the undergraduate organic chemistry laboratory has been previously described (Nason et al, 2017). To date, our attention has been focused on the synthesis of derivatives of the 1,3,4-oxathiazol-2-one heterocycle because of the relative ease of preparation and, until recently, the limited research studying the chemistry of the heterocycle family.…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis and crystal structure of 3-phenyl-1,4,2-dithiazole-5-thione

2022

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In the title compound, C8H5NS3, the dihedral angle between the heterocyclic ring and the phenyl ring is 2.62 (5)°. In the extended structure, aromatic π–π stacking between the 1,4,2-dithiazole-5-thione moiety and the phenyl ring is observed [centroid–centroid distances = 3.717 (6) and 3.712 (6) Å]. The almost planar molecules arrange themselves in parallel chains of head-to-tail molecules oriented by a network of weak C—H...S contacts close to the sum of their van der Waals radii within the chains. All the hydrogen atoms participate in hydrogen-bonding interactions with the sulfur and nitrogen atoms of adjacent molecules. C=S...S contacts between the chains that are significantly shorter than the sum of their van der Waals radii also impact the overall packing.

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Synthesis and crystal structures of halogenated oxathiazolones and an unexpected propanamide

et al. 2023

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The known 1,3,4-oxathiazol-2-ones with crystal structures reported in the Cambridge Structural Database are limited (13 to date) and this article expands the library to 15. In addition, convenient starting materials for the future exploration of 1,3,4-oxathiazol-2-ones are detailed. An unexpected halogenated propanamide has also been identified as a by-product of one reaction, presumably reacting with HCl generated in situ. The space group of 5-[(E)-2-chloroethenyl]-1,3,4-oxathiazol-2-one, C4H2ClNO2S, (1), is P21, with a high Z′ value of 6; the space group of rac-2,3-dibromo-3-chloropropanamide, C3H4Br2ClNO, (2), is P21, with Z′ = 4; and the structure of rac-5-(1,2-dibromo-2-phenylethyl)-1,3,4-oxathiazol-2-one, C10H7Br2NO2S, (3), crystallizes in the space group Pca21, with Z′ = 1. Both of the structures of compounds 2 and 3 are modeled with two-component disorder and each molecular site hosts both of the enantiomers of the racemic pairs (S,S)/(R,R) and (R,S)/(S,R), respectively.

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Crystal structure determination as part of an ongoing undergraduate organic laboratory project: 5-[(E)-styryl]-1,3,4-oxathiazol-2-one

Cited by 3 publications

References 16 publications

The crystal structures of two isomers of 5-(phenylisothiazolyl)-1,3,4-oxathiazol-2-one

The crystal structures of two isomers of 5-(phenylisothiazolyl)-1,3,4-oxathiazol-2-one

Synthesis and crystal structure of 3-phenyl-1,4,2-dithiazole-5-thione

Synthesis and crystal structures of halogenated oxathiazolones and an unexpected propanamide

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