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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">The crystal structures of two isomers of 5-(phenylisothiazolyl)-1,3,4-oxathiazol-2-one</title>
<author><name sortKey="Zhu, Shuguang" sort="Zhu, Shuguang" uniqKey="Zhu S" first="Shuguang" last="Zhu">Shuguang Zhu</name>
<affiliation><nlm:aff id="a">Teva Pharmaceuticals, 3333 N Torrey Pines Ct, Suite 400, La Jolla, CA 92130</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Schriver, Melbourne J" sort="Schriver, Melbourne J" uniqKey="Schriver M" first="Melbourne J." last="Schriver">Melbourne J. Schriver</name>
<affiliation><nlm:aff id="b">Department of Chemistry, Crandall University, PO Box 6004, Moncton, New Brunswick, E1C 9L7,<country>Canada</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Hendsbee, Arthur D" sort="Hendsbee, Arthur D" uniqKey="Hendsbee A" first="Arthur D." last="Hendsbee">Arthur D. Hendsbee</name>
<affiliation><nlm:aff id="c">The Atlantic Centre for Green Chemistry and the Department of Chemistry, Saint Mary’s University, Halifax, Nova Scotia, B3H 3C3,<country>Canada</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Masuda, Jason D" sort="Masuda, Jason D" uniqKey="Masuda J" first="Jason D." last="Masuda">Jason D. Masuda</name>
<affiliation><nlm:aff id="c">The Atlantic Centre for Green Chemistry and the Department of Chemistry, Saint Mary’s University, Halifax, Nova Scotia, B3H 3C3,<country>Canada</country>
</nlm:aff>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PMC</idno>
<idno type="pmid">29152360</idno>
<idno type="pmc">5683500</idno>
<idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683500</idno>
<idno type="RBID">PMC:5683500</idno>
<idno type="doi">10.1107/S2056989017015067</idno>
<date when="2017">2017</date>
<idno type="wicri:Area/Pmc/Corpus">000981</idno>
<idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000981</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">The crystal structures of two isomers of 5-(phenylisothiazolyl)-1,3,4-oxathiazol-2-one</title>
<author><name sortKey="Zhu, Shuguang" sort="Zhu, Shuguang" uniqKey="Zhu S" first="Shuguang" last="Zhu">Shuguang Zhu</name>
<affiliation><nlm:aff id="a">Teva Pharmaceuticals, 3333 N Torrey Pines Ct, Suite 400, La Jolla, CA 92130</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Schriver, Melbourne J" sort="Schriver, Melbourne J" uniqKey="Schriver M" first="Melbourne J." last="Schriver">Melbourne J. Schriver</name>
<affiliation><nlm:aff id="b">Department of Chemistry, Crandall University, PO Box 6004, Moncton, New Brunswick, E1C 9L7,<country>Canada</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Hendsbee, Arthur D" sort="Hendsbee, Arthur D" uniqKey="Hendsbee A" first="Arthur D." last="Hendsbee">Arthur D. Hendsbee</name>
<affiliation><nlm:aff id="c">The Atlantic Centre for Green Chemistry and the Department of Chemistry, Saint Mary’s University, Halifax, Nova Scotia, B3H 3C3,<country>Canada</country>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Masuda, Jason D" sort="Masuda, Jason D" uniqKey="Masuda J" first="Jason D." last="Masuda">Jason D. Masuda</name>
<affiliation><nlm:aff id="c">The Atlantic Centre for Green Chemistry and the Department of Chemistry, Saint Mary’s University, Halifax, Nova Scotia, B3H 3C3,<country>Canada</country>
</nlm:aff>
</affiliation>
</author>
</analytic>
<series><title level="j">Acta Crystallographica Section E: Crystallographic Communications</title>
<idno type="eISSN">2056-9890</idno>
<imprint><date when="2017">2017</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en"><p>The 3,5-isomer of the title compound contains two almost planar molecules in the asymmetric unit, whereas the 3,4-isomer contains a single substantially twisted molecule. Both crystal structures feature short S⋯N and S⋯O interactions.</p>
</div>
</front>
<back><div1 type="bibliography"><listBibl><biblStruct></biblStruct>
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</TEI>
<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Acta Crystallogr E Crystallogr Commun</journal-id>
<journal-id journal-id-type="iso-abbrev">Acta Crystallogr E Crystallogr Commun</journal-id>
<journal-id journal-id-type="publisher-id">Acta Cryst. E</journal-id>
<journal-title-group><journal-title>Acta Crystallographica Section E: Crystallographic Communications</journal-title>
</journal-title-group>
<issn pub-type="epub">2056-9890</issn>
<publisher><publisher-name>International Union of Crystallography</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">29152360</article-id>
<article-id pub-id-type="pmc">5683500</article-id>
<article-id pub-id-type="publisher-id">hb7705</article-id>
<article-id pub-id-type="doi">10.1107/S2056989017015067</article-id>
<article-id pub-id-type="coden">ACSECI</article-id>
<article-id pub-id-type="pii">S2056989017015067</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Research Communications</subject>
</subj-group>
</article-categories>
<title-group><article-title>The crystal structures of two isomers of 5-(phenylisothiazolyl)-1,3,4-oxathiazol-2-one</article-title>
<alt-title><italic>C<sub>11</sub>
H<sub>6</sub>
N<sub>2</sub>
O<sub>2</sub>
S<sub>2</sub>
and C<sub>11</sub>
H<sub>6</sub>
N<sub>2</sub>
O<sub>2</sub>
S<sub>2</sub>
</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Zhu</surname>
<given-names>Shuguang</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><contrib-id contrib-id-type="orcid" authenticated="true">https://orcid.org/0000-0002-2107-7280</contrib-id>
<name><surname>Schriver</surname>
<given-names>Melbourne J.</given-names>
</name>
<xref ref-type="aff" rid="b">b</xref>
<xref ref-type="corresp" rid="cor">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Hendsbee</surname>
<given-names>Arthur D.</given-names>
</name>
<xref ref-type="aff" rid="c">c</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Masuda</surname>
<given-names>Jason D.</given-names>
</name>
<xref ref-type="aff" rid="c">c</xref>
</contrib>
<aff id="a"><label>a</label>
Teva Pharmaceuticals, 3333 N Torrey Pines Ct, Suite 400, La Jolla, CA 92130</aff>
<aff id="b"><label>b</label>
Department of Chemistry, Crandall University, PO Box 6004, Moncton, New Brunswick, E1C 9L7,<country>Canada</country>
</aff>
<aff id="c"><label>c</label>
The Atlantic Centre for Green Chemistry and the Department of Chemistry, Saint Mary’s University, Halifax, Nova Scotia, B3H 3C3,<country>Canada</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>mel.schriver@crandallu.ca</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>11</month>
<year>2017</year>
</pub-date>
<pub-date pub-type="epub"><day>20</day>
<month>10</month>
<year>2017</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>20</day>
<month>10</month>
<year>2017</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the . </pmc-comment>
<volume>73</volume>
<issue>Pt 11</issue>
<issue-id pub-id-type="publisher-id">e171100</issue-id>
<fpage>1726</fpage>
<lpage>1731</lpage>
<history><date date-type="received"><day>14</day>
<month>9</month>
<year>2017</year>
</date>
<date date-type="accepted"><day>16</day>
<month>10</month>
<year>2017</year>
</date>
</history>
<permissions><copyright-statement>© Zhu et al. 2017</copyright-statement>
<copyright-year>2017</copyright-year>
<license license-type="open-access" xlink:href="http://creativecommons.org/licenses/by/2.0/uk/"><license-p>This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted
use, distribution, and reproduction in any medium, provided the original authors and source are cited.</license-p>
<ali:license_ref>http://creativecommons.org/licenses/by/2.0/uk/</ali:license_ref>
</license>
</permissions>
<self-uri xlink:href="https://doi.org/10.1107/S2056989017015067">A full version of this article is available from Crystallography Journals Online.</self-uri>
<abstract abstract-type="toc"><p>The 3,5-isomer of the title compound contains two almost planar molecules in the asymmetric unit, whereas the 3,4-isomer contains a single substantially twisted molecule. Both crystal structures feature short S⋯N and S⋯O interactions.</p>
</abstract>
<abstract><p>The syntheses and crystal structures of two isomers of phenyl isothiazolyl oxathiazolone, C<sub>11</sub>
H<sub>6</sub>
N<sub>2</sub>
O<sub>2</sub>
S<sub>2</sub>
, 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 S⋯N [3.072 (2) Å] and S⋯O contacts [3.089 (1) Å]. The tetramers are π-stacked parallel to the <italic>a</italic>
-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 π-conjugation between the heteroaromatic isothiazoloyl ring and the non-aromatic oxathiazolone heterocycle. In the crystal of isomer (II), the strong S⋯O [3.020 (1) Å] and S⋯C contacts [3.299 (2) Å] and the non-planar structure of the molecule lead to a form of π-stacking not observed in isomer (I) or other oxathiazolone derivatives.</p>
</abstract>
<kwd-group><kwd>crystal structure</kwd>
<kwd>isothiazoyl</kwd>
<kwd>oxathiazolone</kwd>
<kwd>conjugation</kwd>
<kwd>nitrile sulfide</kwd>
<kwd>π-stacking</kwd>
</kwd-group>
</article-meta>
</front>
<body><sec id="sec1"><title>Chemical context </title>
<p>Compounds containing the isothiazolyl moiety are well known in organic and pharmacological research, with extensive reviews on the synthesis and chemistry of the ring (Abdel-Sattar & Elgazwy, 2003<xref ref-type="bibr" rid="bb8"> ▸</xref>
) and the medicinal and industrial uses of compounds containing the isothiazolyl heterocycle (Kaberdin & Potkin 2002<xref ref-type="bibr" rid="bb14"> ▸</xref>
). The solid-state structural features of isothiazole derivatives have been reviewed (Abdel-Sattar & Elgazwy, 2003<xref ref-type="bibr" rid="bb8"> ▸</xref>
). In general, the isothiazolyl ring is recognised as a heteroaromatic ring with extensive π-delocalization (incorporating the empty sulfur 3<italic>d</italic>
-orbitals) within the ring leading to almost planar heterocycles.</p>
<p>Derivatives of the oxathiazolone heterocycle have been known since their first preparation fifty years ago (Muhlbauer & Weiss, 1967<xref ref-type="bibr" rid="bb21"> ▸</xref>
). The facile synthesis of the heterocycle from commercially available amides reacting with chlorocarbonyl sulfenyl chloride under a range of conditions has resulted in the publication of significant libraries of substituted oxathiazolone compounds (Senning & Rasmussen, 1973<xref ref-type="bibr" rid="bb26"> ▸</xref>
; Howe <italic>et al.</italic>
, 1978<xref ref-type="bibr" rid="bb13"> ▸</xref>
; Lin <italic>et al.</italic>
, 2009<xref ref-type="bibr" rid="bb18"> ▸</xref>
; Fordyce <italic>et al.</italic>
, 2010<xref ref-type="bibr" rid="bb10"> ▸</xref>
; Russo <italic>et al.</italic>
, 2015<xref ref-type="bibr" rid="bb24"> ▸</xref>
) leading to hundreds of known oxathiazolone derivatives. The predominant chemistry of the heterocycle has been the thermal cycloreversion to the short lived nitrile sulfide [<italic>R</italic>
—C≡N<sup>(+)</sup>
—S<sup>(−)</sup>
] , a propargyl allenyl 1,3-dipole, which can be trapped by electron-deficient π bonds in reasonable yield to give families of new heterocycles (Paton, 1989<xref ref-type="bibr" rid="bb23"> ▸</xref>
), including isothiazole derivatives. As a result of the electronic properties of the short-lived nitrile sulfide intermediates, optimal conditions for cyclization require trapping reactions with electron-deficient dipolariphiles. Industrially, various derivatives of the oxathiazolone heterocycle have been reported as potential fungicides (Klaus <italic>et al.</italic>
, 1965<xref ref-type="bibr" rid="bb15"> ▸</xref>
), pesticides (Hölzl, 2004<xref ref-type="bibr" rid="bb12"> ▸</xref>
) and as polymer additives (Crosby 1978<xref ref-type="bibr" rid="bb6"> ▸</xref>
). More recently, the medicinal properties of the oxathiazolone heterocycle have been explored as selective inhibitors for tuberculosis (Lin <italic>et al.</italic>
, 2009<xref ref-type="bibr" rid="bb18"> ▸</xref>
), inflammatory diseases (Fan <italic>et al.</italic>
, 2014<xref ref-type="bibr" rid="bb9"> ▸</xref>
) and as proteasome inhibitors (Russo <italic>et al.</italic>
, 2015<xref ref-type="bibr" rid="bb24"> ▸</xref>
).</p>
<p>In previous structural studies on oxathiazolone compounds, the non-aromatic heterocyclic rings were found to be planar with largely localized C=N and C=O double bonds. The extent of π-delocalization within the oxathiazolone ring and to the substituent group and the effect on the structure and chemical properties have been discussed spectroscopically (Markgraf <italic>et al.</italic>
, 2007<xref ref-type="bibr" rid="bb19"> ▸</xref>
) and structurally (Krayushkin <italic>et al.</italic>
, 2010<italic>a</italic>
<xref ref-type="bibr" rid="bb16"> ▸</xref>
,<italic>b</italic>
<xref ref-type="bibr" rid="bb17"> ▸</xref>
). Our interest in this system was prompted by the possibility that catenated systems of isothiazolone heterocycles may have useful electronic properties as the number of π systems is increased.<chem-struct id="scheme1"><graphic xlink:href="e-73-01726-scheme1.jpg" position="float" orientation="portrait"></graphic>
</chem-struct>
</p>
</sec>
<sec id="sec2"><title>Structural commentary </title>
<p>There are two independent molecules in the asymmetric unit of (I)<xref ref-type="chem" rid="scheme1"></xref>
(Fig. 1<xref ref-type="fig" rid="fig1"> ▸</xref>
). In general, the two molecules are not significantly different with the exception of the C—S bonds in the oxathiazolone rings. In one of the molecules, the C1—S1 distance [1.762 (2) Å] is longer than the same bond in the second molecule, C12—S3 [1.746 (2) Å]. The difference may arise from the nature of the intermolecular contacts to the sulfur atoms, with a strong pair of co-planar S⋯N contacts [3.086 (2) Å] in the first molecule but only one S⋯N contact [3.072 (2) Å] in the second molecule (which is also twisted out of the plane of the molecule). These differences are due to the position of the independent molecules in the tetramer that will be described below. For the purposes of further structural analysis, we will restrict our discussion to the first molecule in the asymmetric unit. The asymmetric unit of (II)<xref ref-type="chem" rid="scheme1"></xref>
is shown in Fig. 2<xref ref-type="fig" rid="fig2"> ▸</xref>
.</p>
<p>The bond distances and angles within the terminal phenyl rings in compounds (I)<xref ref-type="chem" rid="scheme1"></xref>
and (II)<xref ref-type="chem" rid="scheme1"></xref>
are not significantly different from the those reported for related compounds (Schriver & Zaworotko, 1995<xref ref-type="bibr" rid="bb25"> ▸</xref>
; Krayushkin <italic>et al.</italic>
, 2010<italic>a</italic>
<xref ref-type="bibr" rid="bb16"> ▸</xref>
,<italic>b</italic>
<xref ref-type="bibr" rid="bb17"> ▸</xref>
). The sum of the endocyclic bond angles in the isothiazole moieties for both (I)<xref ref-type="chem" rid="scheme1"></xref>
and (II)<xref ref-type="chem" rid="scheme1"></xref>
(540.0°) is consistent with planar (ideal sum = 540°) π-delocalized five-membered rings, as expected. The bond lengths of the endocyclic bonds in the isothiazolyl moieties in (I)<xref ref-type="chem" rid="scheme1"></xref>
and (II)<xref ref-type="chem" rid="scheme1"></xref>
are not significantly (δ > 3σ) different from the statistical averages from previous structural studies (Bridson <italic>et al.</italic>
, 1994<xref ref-type="bibr" rid="bb3"> ▸</xref>
, 1995<xref ref-type="bibr" rid="bb4"> ▸</xref>
). While the C=N bonds in the isothiazolyl rings of (I)<xref ref-type="chem" rid="scheme1"></xref>
[1.327 (3) Å] and (II)<xref ref-type="chem" rid="scheme1"></xref>
[1.321 (2) Å] and the C=C bonds in (I)<xref ref-type="chem" rid="scheme1"></xref>
[1.361 (3) Å] and (II)<xref ref-type="chem" rid="scheme1"></xref>
[1.374 (2) Å] are mostly longer than the statistical averages for C=N [1.308 ± 0.016 Å] and C=C bonds [1.369 ± 0.002 Å], the differences are not sufficient to warrant an assessment of their cause or their effect on the structure.</p>
<p>The bond distances and angles within the oxathiazolone rings in compounds (I)<xref ref-type="chem" rid="scheme1"></xref>
and (II)<xref ref-type="chem" rid="scheme1"></xref>
are not significantly different (δ ≥ 3σ) from the statistical averages for published crystal structures (Schriver & Zaworotko, 1995<xref ref-type="bibr" rid="bb25"> ▸</xref>
; Bridson <italic>et al.</italic>
1994<xref ref-type="bibr" rid="bb3"> ▸</xref>
, 1995<xref ref-type="bibr" rid="bb4"> ▸</xref>
; Vorontsova <italic>et al.</italic>
, 1996<xref ref-type="bibr" rid="bb28"> ▸</xref>
; McMillan <italic>et al.</italic>
, 2006<xref ref-type="bibr" rid="bb20"> ▸</xref>
; Krayushkin <italic>et al.</italic>
, 2010<italic>a</italic>
<xref ref-type="bibr" rid="bb16"> ▸</xref>
,<italic>b</italic>
<xref ref-type="bibr" rid="bb17"> ▸</xref>
; Nason <italic>et al.</italic>
, 2017<xref ref-type="bibr" rid="bb22"> ▸</xref>
). The sum of the endocyclic bond angles in the oxathiazolone rings for both (I)<xref ref-type="chem" rid="scheme1"></xref>
and (II)<xref ref-type="chem" rid="scheme1"></xref>
(540.0°) is consistent with planar rings (ideal sum = 540°). The S—N bonds in the oxathiazolone rings of (I)<xref ref-type="chem" rid="scheme1"></xref>
[1.685 (2) Å] and (II)<xref ref-type="chem" rid="scheme1"></xref>
[1.682 (1) Å], the C<sub>sub</sub>
—O bonds in (I)<xref ref-type="chem" rid="scheme1"></xref>
[1.364 (2) Å] and (II)<xref ref-type="chem" rid="scheme1"></xref>
[1.375 (1) Å] and the inter-ring C<italic>sp</italic>
<sup>2</sup>
—C<italic>sp</italic>
<sup>2</sup>
bonds in (I)<xref ref-type="chem" rid="scheme1"></xref>
[1.449 (3) Å] and (II)<xref ref-type="chem" rid="scheme1"></xref>
[1.451 (2) Å] are all consistently shorter than the statistical averages for S—N [1.696 ± 0.022 Å], C<sub>sub</sub>
—O [1.392 ± 0.030 Å] and C=C bonds [1.461 ± 0.025 Å]. These differences, however, are not sufficient to warrant an assessment of their cause or their effect on the structure.</p>
<p>The three rings in the molecules of (I)<xref ref-type="chem" rid="scheme1"></xref>
are nearly co-planar, with the dihedral angles between central isothiazolyl ring and the pendant oxathiazolone and phenyl rings being 3.06 (11) and 1.10 (12)°, respectively, for the S1 molecule and 2.62 (9) and 6.84 (10)°, respectively, for the S3 molecule. Overall r.m.s. deviations for the S1 and S3 molecules are 0.032 and 0.063 Å, respectively. In contrast to the near planarity of both asymmetric molecules of (I)<xref ref-type="chem" rid="scheme1"></xref>
, the single molecule of (II)<xref ref-type="chem" rid="scheme1"></xref>
features significant twists between the central isothiazolyl ring and the pendant oxathiazolone and phenyl rings [dihedral angles of 13.27 (6) and 61.18 (7)°, respectively], which may be ascribed to steric crowding. It has been argued, based on spectroscopic and structural evidence, that π-delocalization extends between the rings of oxathiazolone heterocycles attached to aromatic rings, resulting in observable differences (Schriver & Zaworotko, 1995<xref ref-type="bibr" rid="bb25"> ▸</xref>
; Krayushkin <italic>et al.</italic>
, 2010<italic>a</italic>
<xref ref-type="bibr" rid="bb16"> ▸</xref>
,<italic>b</italic>
<xref ref-type="bibr" rid="bb17"> ▸</xref>
; Markgraf <italic>et al.</italic>
, 2007<xref ref-type="bibr" rid="bb19"> ▸</xref>
). In this work it can be seen that nearly identical molecules result, even when torsion angles are present that would effectively disrupt any π conjugation between the rings, suggesting that the presence or absence of inter-ring π delocalization does not have a significant effect on the structure of the molecules.</p>
</sec>
<sec id="sec3"><title>Supramolecular features </title>
<p>In all previous reports on the solid-state structures of compounds containing the oxathiazolone heterocycle, the intermolecular interactions have been ignored or described as insignificant, with the exception of the recent observation of π-stacking in the styryl derivative (Nason <italic>et al.</italic>
, 2017<xref ref-type="bibr" rid="bb22"> ▸</xref>
). The strongest intermolecular contacts in (I)<xref ref-type="chem" rid="scheme1"></xref>
are S3⋯N3 [3.086 (2) Å], S1⋯N4 [3.072 (2) Å] and S4⋯O1 [3.089 (1) Å] (Fig. 3<xref ref-type="fig" rid="fig3"> ▸</xref>
). The S3⋯N3 contacts assist in the formation of a co-planar pair of identical molecules within the asymmetric unit. The other molecules in the asymmetric unit are connected <italic>via</italic>
the S1⋯N4 [3.072 (2) Å] and S4⋯O1 [3.089 (1) Å] contacts. Taken together, the contacts between two pairs of identical molecules in the asymmetric unit form a centrosymmetric tetramer that in turn form π-stacks parallel to the <italic>a</italic>
axis. The intermolecular contacts between sulfur and nitrogen and oxygen have been observed in another oxathiazolone ring that also resulted in π-stacking of the planar molecules (Nason <italic>et al.</italic>
, 2017<xref ref-type="bibr" rid="bb22"> ▸</xref>
).</p>
<p>The strongest intermolecular contacts in (II)<xref ref-type="chem" rid="scheme1"></xref>
are S2⋯O2 [3.020 (1) Å], S1⋯C10 [3.299 (2) Å] and C4⋯O2 [3.100 (2) Å] (Fig. 4<xref ref-type="fig" rid="fig4"> ▸</xref>
). The C4⋯O2 contact, while significantly shorter than the sum of van der Waals radii for the atoms, is to some extent, the result of the adjacent stronger S2⋯O2 contact. The geometry of the molecule (II)<xref ref-type="chem" rid="scheme1"></xref>
reduces the opportunity for the formation of π-stacks but it is observed that the centroid of the terminal phenyl ring is 3.632 (2) Å above and parallel to the nearly planar portion of an adjacent molecule formed by the two heterocyclic rings (Fig. 4<xref ref-type="fig" rid="fig4"> ▸</xref>
).</p>
<sec id="sec3.1"><title>Database survey </title>
<p>A search of the Cambridge Structural Database (Version 5.38; Groom <italic>et al.</italic>
, 2016<xref ref-type="bibr" rid="bb11"> ▸</xref>
) revealed that eleven crystal structures of oxathiazolone derivatives in peer-reviewed journals have been reported previously (Bridson <italic>et al.</italic>
, 1994<xref ref-type="bibr" rid="bb3"> ▸</xref>
, 1995<xref ref-type="bibr" rid="bb4"> ▸</xref>
; Schriver & Zaworotko, 1995<xref ref-type="bibr" rid="bb25"> ▸</xref>
; Vorontsova <italic>et al.</italic>
, 1996<xref ref-type="bibr" rid="bb28"> ▸</xref>
; McMillan <italic>et al.</italic>
, 2006<xref ref-type="bibr" rid="bb20"> ▸</xref>
; Krayushkin <italic>et al.</italic>
, 2010<italic>a</italic>
<xref ref-type="bibr" rid="bb16"> ▸</xref>
,<italic>b</italic>
<xref ref-type="bibr" rid="bb17"> ▸</xref>
; Nason <italic>et al.</italic>
, 2017<xref ref-type="bibr" rid="bb22"> ▸</xref>
), which have been partially reviewed (McMillan <italic>et al.</italic>
, 2006<xref ref-type="bibr" rid="bb20"> ▸</xref>
and Krayushkin <italic>et al.</italic>
, 2010<italic>a</italic>
<xref ref-type="bibr" rid="bb16"> ▸</xref>
,<italic>b</italic>
<xref ref-type="bibr" rid="bb17"> ▸</xref>
). An additional five X-ray oxathiazolone crystal structures have been reported in theses (Demas, 1982<xref ref-type="bibr" rid="bb7"> ▸</xref>
; Zhu, 1997<xref ref-type="bibr" rid="bb29"> ▸</xref>
). There are also two published gas-phase electron-diffraction structures of oxathiazolone derivatives (Bak <italic>et al.</italic>
, 1978<xref ref-type="bibr" rid="bb2"> ▸</xref>
, 1982<xref ref-type="bibr" rid="bb1"> ▸</xref>
). The structures fall into two groups: those that feature a C<italic>sp</italic>
<sup>2</sup>
—C<italic>sp</italic>
<sup>3</sup>
bond between the heterocycle and the saturated organic substituent and those that feature a C<italic>sp</italic>
<sup>2</sup>
—C<italic>sp</italic>
<sup>2</sup>
bond between the heterocycle and the unsaturated organic substituent (either a phenyl group, heterocyclic ring or alkenyl moiety).</p>
</sec>
</sec>
<sec id="sec4"><title>Synthesis and crystallization </title>
<p><bold>Compound (I)</bold>
was prepared following a local variation of literature methods (Howe <italic>et al.</italic>
, 1978<xref ref-type="bibr" rid="bb13"> ▸</xref>
). 3-Phenylisothiazole-4-carbonamide (Zhu, 1997<xref ref-type="bibr" rid="bb29"> ▸</xref>
) (2.90 g, 14.2 mmol) was placed in 50 ml of toluene under nitrogen and chlorocarbonyl sulfenyl chloride (4.20 g, 32.0 mmol, approximately 2 × molar excess) was added dropwise to the stirred solution. The resulting mixture was heated (363–373 K) under nitrogen for 1.5 h and allowed to evaporate to a solid residue. The evaporate was recrystallized from toluene solution to give colourless needle-shaped crystals (Fig. 5<xref ref-type="fig" rid="fig5"> ▸</xref>
) (3.20 g, 12.2 mmol, 86%). Elemental analysis: calculated % (Found %): 50.35 (50.2); H 2.3 (2.4); N 10.7 (10.7). IR (KBr): 3100 (<italic>w</italic>
), 1812 (<italic>w</italic>
), 1749 (<italic>s</italic>
), 1735 (<italic>s</italic>
), 1598 (<italic>s</italic>
), 1182 (<italic>m</italic>
), 1088 (<italic>m</italic>
), 1014 (<italic>w</italic>
), 959 (<italic>s</italic>
), 884 (<italic>ms</italic>
). 834 (<italic>ms</italic>
), 765 (<italic>s</italic>
), 734 (<italic>s</italic>
), 692 (<italic>ms</italic>
). <sup>1</sup>
H NMR (400 MHz, CDCl<sub>3</sub>
, δ p.p.m.): 9.28 (5, 1H), 7.61 (<italic>m</italic>
, 2H), 7.46 (<italic>m</italic>
, 3H). <sup>13</sup>
C NMR (100 MHz, CDCl<sub>3</sub>
, δ p.p.m.): 172.7,167.0, 154.1, 152.1, 134.0, 129.6, 129.0, 128.2, 123.3. MS (EI): C<sub>11</sub>
H<sub>6</sub>
N<sub>2</sub>
O<sub>2</sub>
S<sub>2</sub>
requires (<italic>M</italic>
<sup>+</sup>
), 262.301, found <italic>m</italic>
/<italic>e</italic>
(%, assign.): 262 (22, <italic>M</italic>
+), 218 (2, <italic>M-</italic>
-CO<sub>2</sub>
), 188 (78, <italic>M</italic>
–CONS), 186 (100, C<sub>6</sub>
H<sub>5</sub>
[CCCNS)CN), 160 (1 3, <italic>M</italic>
–COCONS), 135 (26, C<sub>6</sub>
H<sub>5</sub>
CNS), 103 (13, C<sub>6</sub>
H<sub>5</sub>
CN), 77 (29, C<sub>6</sub>
H<sub>5</sub>
). UV–visible spectroscopy (hexane) λ<sub>xax</sub>
(log ∊) : 275–230 nm (4.11), 197 nm (4.72).</p>
<p><bold>Compound (II)</bold>
prepared following a local variation of literature methods (Howe <italic>et al.</italic>
, 1978<xref ref-type="bibr" rid="bb13"> ▸</xref>
). 3-Phenylisothiazole-5-carbonamide (Zhu, 1997<xref ref-type="bibr" rid="bb29"> ▸</xref>
) (4.08 g, 20.0 mmol) was placed in 50 ml of toluene under nitrogen and chlorocarbonyl sulfenyl chloride (6.50 g, 50.0 mmol, approximately 2.5 × molar excess) was added dropwise to the stirred solution. The resulting mixture was heated (363–373 K) under nitrogen for 8.5 h and allowed to evaporate to a solid residue (6.093 g). The evaporate was recrystallized from toluene solution to give colourless block-shaped crystals (Fig. 6<xref ref-type="fig" rid="fig6"> ▸</xref>
) (4.20 g, 20.6 mmol, 83%), Elemental analysis: calculated % (found%) 50.35 (50.0); H 2.3 (2.35); N 10.7 (10.5). IR (KBr): 3097 (<italic>w</italic>
), 3066 (<italic>w</italic>
), 3032 (<italic>w</italic>
), 1813 (<italic>ms</italic>
), 1759 (<italic>s</italic>
), 1738 (<italic>s</italic>
), 1600 (<italic>ms</italic>
), 1590 (<italic>ms</italic>
), 1517 (<italic>s</italic>
), 1496 (<italic>s</italic>
), 1055 (<italic>ms</italic>
), 973 (<italic>s</italic>
), 902 (<italic>s</italic>
), 776 (<italic>s</italic>
), 695 (<italic>s</italic>
) cm<sup>−1. 1</sup>
H NMR (400 MHz, CDCl<sub>3</sub>
, δ p.p.m.): 7.425–7.487 (<italic>m</italic>
, 3H), 7.906–7.937 (<italic>m</italic>
, 2H), 7.976 (5, 1H). <sup>13</sup>
C NMR (100MHz, CDCl<sub>3</sub>
, δ p.p.m.): 171.5, 167.9, 150.7, 150.5, 133.4, 129.9, 128.9, 126.8, 122.5. MS (EI): C<sub>11</sub>
H<sub>6</sub>
N<sub>2</sub>
O<sub>2</sub>
S<sub>2</sub>
requires (<italic>M</italic>
<sup>+</sup>
), 262.301, found <italic>m</italic>
/<italic>e</italic>
(%, assign.): 262 (52, <italic>M</italic>
+), 218 (3, M-CO<sub>2</sub>
), 188 (100, <italic>M</italic>
–CONS), 160 (9, <italic>M</italic>
–COCONS), 135 (2, <italic>M</italic>
–HC–CCOCONS). UV–visible spectroscopy (hexane) λ<sub>xax</sub>
(log ∊) : 283 nm (4.25), 248 nm (4.36), 203 nm (94.49).</p>
</sec>
<sec id="sec5"><title>Refinement </title>
<p>Crystal data, data collection and structure refinement details are summarized in Table 1<xref ref-type="table" rid="table1"> ▸</xref>
. H atoms were positioned geometrically (C—H = 0.93 Å) and refined as riding with <italic>U</italic>
<sub>iso</sub>
(H) = 1.2<italic>U</italic>
<sub>eq</sub>
(C).</p>
</sec>
<sec sec-type="supplementary-material"><title>Supplementary Material</title>
<supplementary-material content-type="local-data"><p>Crystal structure: contains datablock(s) I, II, ms003_0m. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989017015067/hb7705sup1.cif">10.1107/S2056989017015067/hb7705sup1.cif</ext-link>
</p>
<media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-73-01726-sup1.cif" orientation="portrait" id="d35e163" position="anchor"></media>
</supplementary-material>
<supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989017015067/hb7705Isup2.hkl">10.1107/S2056989017015067/hb7705Isup2.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-73-01726-Isup2.hkl" orientation="portrait" id="d35e170" position="anchor"></media>
</supplementary-material>
<supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) II. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989017015067/hb7705IIsup3.hkl">10.1107/S2056989017015067/hb7705IIsup3.hkl</ext-link>
</p>
<media mimetype="text" mime-subtype="plain" xlink:href="e-73-01726-IIsup3.hkl" orientation="portrait" id="d35e177" position="anchor"></media>
</supplementary-material>
<supplementary-material content-type="local-data"><media xlink:href="e-73-01726-Isup4.cml"><caption><p>Click here for additional data file.</p>
</caption>
</media>
<p>Supporting information file. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989017015067/hb7705Isup4.cml">10.1107/S2056989017015067/hb7705Isup4.cml</ext-link>
</p>
</supplementary-material>
<supplementary-material content-type="local-data"><media xlink:href="e-73-01726-IIsup5.cml"><caption><p>Click here for additional data file.</p>
</caption>
</media>
<p>Supporting information file. DOI: <ext-link ext-link-type="uri" xlink:href="https://doi.org/10.1107/S2056989017015067/hb7705IIsup5.cml">10.1107/S2056989017015067/hb7705IIsup5.cml</ext-link>
</p>
</supplementary-material>
<supplementary-material content-type="local-data"><p>CCDC references: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1580338">1580338</ext-link>
, <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1580337">1580337</ext-link>
</p>
</supplementary-material>
<supplementary-material content-type="local-data"><p>Additional supporting information: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?hb7705&file=hb7705sup0.html&mime=text/html"> crystallographic information</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?hb7705sup1&Qmime=cif">3D view</ext-link>
; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?hb7705&checkcif=yes">checkCIF report</ext-link>
</p>
</supplementary-material>
</sec>
</body>
<back><ack><p>SZ and MJS thank John Bridson and David Miller of the Chemistry Department of Memorial University for preliminary crystallographic work. MS would like to acknowledge the work of many student co-workers in the course Chemistry 2113 who worked on the oxathiazolone synthesis and characterization project, and the support of Crandall University. MS would like to acknowledge the Stephen and Ella Steeves Research Fund for operating funds. JDM would like to acknowledge the Canadian Foundation for Innovation Leaders Opportunity fund (CFI–LFO) for upgrades to the diffractometer, the Natural Science and Engineering Council of Canada (NSERC) for operating funds and Saint Mary’s University for support.</p>
</ack>
<app-group><app><title>supplementary crystallographic information</title>
<sec id="d1e151" sec-type="tablewrapcrystaldatalong"><label>5-(3-Phenylisothiazol-5-yl)-1,3,4-oxathiazol-2-one (I) </label>
<title>Crystal data</title>
<table-wrap position="anchor" id="d1e160"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">C<sub>11</sub>
H<sub>6</sub>
N<sub>2</sub>
O<sub>2</sub>
S<sub>2</sub>
</td>
<td rowspan="1" colspan="1"><italic>Z</italic>
= 4</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
= 262.30</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 536</td>
</tr>
<tr><td rowspan="1" colspan="1">Triclinic, <italic>P</italic>
1</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
= 1.557 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
= 7.2739 (7) Å</td>
<td rowspan="1" colspan="1">Mo <italic>K</italic>
α radiation, λ = 0.71073 Å</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
= 11.2713 (11) Å</td>
<td rowspan="1" colspan="1">Cell parameters from 5699 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
= 14.6909 (15) Å</td>
<td rowspan="1" colspan="1">θ = 2.4–28.6°</td>
</tr>
<tr><td rowspan="1" colspan="1">α = 87.562 (1)°</td>
<td rowspan="1" colspan="1">µ = 0.46 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 78.341 (1)°</td>
<td rowspan="1" colspan="1"><italic>T</italic>
= 296 K</td>
</tr>
<tr><td rowspan="1" colspan="1">γ = 71.624 (1)°</td>
<td rowspan="1" colspan="1">Needle, colourless</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
= 1119.16 (19) Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">0.49 × 0.25 × 0.14 mm</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e285" sec-type="tablewrapdatacollectionlong"><label>5-(3-Phenylisothiazol-5-yl)-1,3,4-oxathiazol-2-one (I) </label>
<title>Data collection</title>
<table-wrap position="anchor" id="d1e294"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Bruker APEXII CCD diffractometer</td>
<td rowspan="1" colspan="1">3485 reflections with <italic>I</italic>
> 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">Radiation source: fine-focus sealed tube</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
= 0.015</td>
</tr>
<tr><td rowspan="1" colspan="1">φ and ω scans</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
= 25.0°, θ<sub>min</sub>
= 1.9°</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (SADABS; Bruker, 2008)</td>
<td rowspan="1" colspan="1"><italic>h</italic>
= −5→8</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
= 0.804, <italic>T</italic>
<sub>max</sub>
= 0.936</td>
<td rowspan="1" colspan="1"><italic>k</italic>
= −13→13</td>
</tr>
<tr><td rowspan="1" colspan="1">7476 measured reflections</td>
<td rowspan="1" colspan="1"><italic>l</italic>
= −17→17</td>
</tr>
<tr><td rowspan="1" colspan="1">3862 independent reflections</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e398" sec-type="tablewraprefinementdatalong"><label>5-(3-Phenylisothiazol-5-yl)-1,3,4-oxathiazol-2-one (I) </label>
<title>Refinement</title>
<table-wrap position="anchor" id="d1e407"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic>
<sup>2</sup>
</td>
<td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td>
</tr>
<tr><td rowspan="1" colspan="1">Least-squares matrix: full</td>
<td rowspan="1" colspan="1">H-atom parameters constrained</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
> 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.031</td>
<td rowspan="1" colspan="1"><italic>w</italic>
= 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0697<italic>P</italic>
)<sup>2</sup>
+ 0.2729<italic>P</italic>
] where <italic>P</italic>
= (<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
+ 2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
)/3</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.106</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
< 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
= 1.04</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
= 0.33 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">3862 reflections</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
= −0.23 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">308 parameters</td>
<td rowspan="1" colspan="1">Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc<sup>*</sup>
=kFc[1+0.001xFc<sup>2</sup>
λ<sup>3</sup>
/sin(2θ)]<sup>-1/4</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">0 restraints</td>
<td rowspan="1" colspan="1">Extinction coefficient: 0.031 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e573" sec-type="specialdetails"><label>5-(3-Phenylisothiazol-5-yl)-1,3,4-oxathiazol-2-one (I) </label>
<title>Special details</title>
<table-wrap position="anchor" id="d1e583"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e592" sec-type="tablewrapcoords"><label>5-(3-Phenylisothiazol-5-yl)-1,3,4-oxathiazol-2-one (I) </label>
<title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e604"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>x</italic>
</td>
<td rowspan="1" colspan="1"><italic>y</italic>
</td>
<td rowspan="1" colspan="1"><italic>z</italic>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sub>iso</sub>
*/<italic>U</italic>
<sub>eq</sub>
</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.85294 (8)</td>
<td rowspan="1" colspan="1">0.03895 (4)</td>
<td rowspan="1" colspan="1">0.15683 (4)</td>
<td rowspan="1" colspan="1">0.05223 (17)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.8238 (2)</td>
<td rowspan="1" colspan="1">0.18576 (13)</td>
<td rowspan="1" colspan="1">0.30252 (9)</td>
<td rowspan="1" colspan="1">0.0593 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.8263 (3)</td>
<td rowspan="1" colspan="1">0.12000 (15)</td>
<td rowspan="1" colspan="1">0.05875 (12)</td>
<td rowspan="1" colspan="1">0.0510 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.8229 (3)</td>
<td rowspan="1" colspan="1">0.17293 (17)</td>
<td rowspan="1" colspan="1">0.22295 (13)</td>
<td rowspan="1" colspan="1">0.0446 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S2</td>
<td rowspan="1" colspan="1">0.77918 (10)</td>
<td rowspan="1" colspan="1">0.29901 (5)</td>
<td rowspan="1" colspan="1">−0.10629 (4)</td>
<td rowspan="1" colspan="1">0.05823 (18)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.7971 (2)</td>
<td rowspan="1" colspan="1">0.27252 (11)</td>
<td rowspan="1" colspan="1">0.16249 (8)</td>
<td rowspan="1" colspan="1">0.0443 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.7537 (3)</td>
<td rowspan="1" colspan="1">0.44255 (17)</td>
<td rowspan="1" colspan="1">−0.14107 (11)</td>
<td rowspan="1" colspan="1">0.0541 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.8016 (3)</td>
<td rowspan="1" colspan="1">0.23440 (17)</td>
<td rowspan="1" colspan="1">0.07498 (12)</td>
<td rowspan="1" colspan="1">0.0415 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S3</td>
<td rowspan="1" colspan="1">0.59888 (8)</td>
<td rowspan="1" colspan="1">0.83750 (5)</td>
<td rowspan="1" colspan="1">0.55508 (4)</td>
<td rowspan="1" colspan="1">0.05152 (17)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">0.6679 (3)</td>
<td rowspan="1" colspan="1">0.59670 (16)</td>
<td rowspan="1" colspan="1">0.59752 (14)</td>
<td rowspan="1" colspan="1">0.0797 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N3</td>
<td rowspan="1" colspan="1">0.4193 (2)</td>
<td rowspan="1" colspan="1">0.89051 (14)</td>
<td rowspan="1" colspan="1">0.49359 (11)</td>
<td rowspan="1" colspan="1">0.0454 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.7806 (3)</td>
<td rowspan="1" colspan="1">0.33109 (18)</td>
<td rowspan="1" colspan="1">0.00604 (12)</td>
<td rowspan="1" colspan="1">0.0415 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S4</td>
<td rowspan="1" colspan="1">0.09624 (8)</td>
<td rowspan="1" colspan="1">0.94818 (4)</td>
<td rowspan="1" colspan="1">0.37616 (4)</td>
<td rowspan="1" colspan="1">0.05119 (17)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">0.4345 (2)</td>
<td rowspan="1" colspan="1">0.68529 (12)</td>
<td rowspan="1" colspan="1">0.51338 (9)</td>
<td rowspan="1" colspan="1">0.0472 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N4</td>
<td rowspan="1" colspan="1">−0.0487 (3)</td>
<td rowspan="1" colspan="1">0.89146 (15)</td>
<td rowspan="1" colspan="1">0.33086 (11)</td>
<td rowspan="1" colspan="1">0.0479 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.7628 (3)</td>
<td rowspan="1" colspan="1">0.45417 (17)</td>
<td rowspan="1" colspan="1">0.01441 (12)</td>
<td rowspan="1" colspan="1">0.0419 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4B</td>
<td rowspan="1" colspan="1">0.7607</td>
<td rowspan="1" colspan="1">0.4931</td>
<td rowspan="1" colspan="1">0.0693</td>
<td rowspan="1" colspan="1">0.050*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.7479 (3)</td>
<td rowspan="1" colspan="1">0.51552 (18)</td>
<td rowspan="1" colspan="1">−0.07130 (12)</td>
<td rowspan="1" colspan="1">0.0410 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.7266 (3)</td>
<td rowspan="1" colspan="1">0.64887 (18)</td>
<td rowspan="1" colspan="1">−0.08776 (13)</td>
<td rowspan="1" colspan="1">0.0425 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.7228 (3)</td>
<td rowspan="1" colspan="1">0.72818 (19)</td>
<td rowspan="1" colspan="1">−0.01704 (14)</td>
<td rowspan="1" colspan="1">0.0503 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H7A</td>
<td rowspan="1" colspan="1">0.7348</td>
<td rowspan="1" colspan="1">0.6969</td>
<td rowspan="1" colspan="1">0.0418</td>
<td rowspan="1" colspan="1">0.060*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.7015 (3)</td>
<td rowspan="1" colspan="1">0.8528 (2)</td>
<td rowspan="1" colspan="1">−0.03326 (18)</td>
<td rowspan="1" colspan="1">0.0604 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8A</td>
<td rowspan="1" colspan="1">0.6980</td>
<td rowspan="1" colspan="1">0.9050</td>
<td rowspan="1" colspan="1">0.0149</td>
<td rowspan="1" colspan="1">0.073*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.6854 (3)</td>
<td rowspan="1" colspan="1">0.9007 (2)</td>
<td rowspan="1" colspan="1">−0.12035 (19)</td>
<td rowspan="1" colspan="1">0.0652 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9A</td>
<td rowspan="1" colspan="1">0.6719</td>
<td rowspan="1" colspan="1">0.9847</td>
<td rowspan="1" colspan="1">−0.1312</td>
<td rowspan="1" colspan="1">0.078*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.6895 (4)</td>
<td rowspan="1" colspan="1">0.8231 (2)</td>
<td rowspan="1" colspan="1">−0.19106 (17)</td>
<td rowspan="1" colspan="1">0.0658 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10A</td>
<td rowspan="1" colspan="1">0.6784</td>
<td rowspan="1" colspan="1">0.8551</td>
<td rowspan="1" colspan="1">−0.2498</td>
<td rowspan="1" colspan="1">0.079*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.7101 (3)</td>
<td rowspan="1" colspan="1">0.6982 (2)</td>
<td rowspan="1" colspan="1">−0.17573 (15)</td>
<td rowspan="1" colspan="1">0.0553 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11A</td>
<td rowspan="1" colspan="1">0.7129</td>
<td rowspan="1" colspan="1">0.6467</td>
<td rowspan="1" colspan="1">−0.2242</td>
<td rowspan="1" colspan="1">0.066*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.5796 (3)</td>
<td rowspan="1" colspan="1">0.68671 (19)</td>
<td rowspan="1" colspan="1">0.56116 (15)</td>
<td rowspan="1" colspan="1">0.0526 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.3557 (3)</td>
<td rowspan="1" colspan="1">0.80060 (16)</td>
<td rowspan="1" colspan="1">0.47969 (12)</td>
<td rowspan="1" colspan="1">0.0396 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.2024 (3)</td>
<td rowspan="1" colspan="1">0.81178 (16)</td>
<td rowspan="1" colspan="1">0.42756 (12)</td>
<td rowspan="1" colspan="1">0.0399 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.1224 (3)</td>
<td rowspan="1" colspan="1">0.72317 (17)</td>
<td rowspan="1" colspan="1">0.40912 (12)</td>
<td rowspan="1" colspan="1">0.0411 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H15A</td>
<td rowspan="1" colspan="1">0.1576</td>
<td rowspan="1" colspan="1">0.6415</td>
<td rowspan="1" colspan="1">0.4299</td>
<td rowspan="1" colspan="1">0.049*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">−0.0219 (3)</td>
<td rowspan="1" colspan="1">0.77277 (16)</td>
<td rowspan="1" colspan="1">0.35387 (12)</td>
<td rowspan="1" colspan="1">0.0400 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">−0.1434 (3)</td>
<td rowspan="1" colspan="1">0.70474 (18)</td>
<td rowspan="1" colspan="1">0.32326 (12)</td>
<td rowspan="1" colspan="1">0.0430 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">−0.2967 (3)</td>
<td rowspan="1" colspan="1">0.7675 (2)</td>
<td rowspan="1" colspan="1">0.27896 (14)</td>
<td rowspan="1" colspan="1">0.0523 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H18A</td>
<td rowspan="1" colspan="1">−0.3229</td>
<td rowspan="1" colspan="1">0.8525</td>
<td rowspan="1" colspan="1">0.2681</td>
<td rowspan="1" colspan="1">0.063*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C19</td>
<td rowspan="1" colspan="1">−0.4109 (3)</td>
<td rowspan="1" colspan="1">0.7038 (2)</td>
<td rowspan="1" colspan="1">0.25083 (15)</td>
<td rowspan="1" colspan="1">0.0595 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H19A</td>
<td rowspan="1" colspan="1">−0.5127</td>
<td rowspan="1" colspan="1">0.7462</td>
<td rowspan="1" colspan="1">0.2207</td>
<td rowspan="1" colspan="1">0.071*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C20</td>
<td rowspan="1" colspan="1">−0.3750 (3)</td>
<td rowspan="1" colspan="1">0.5778 (2)</td>
<td rowspan="1" colspan="1">0.26715 (16)</td>
<td rowspan="1" colspan="1">0.0622 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H20A</td>
<td rowspan="1" colspan="1">−0.4528</td>
<td rowspan="1" colspan="1">0.5355</td>
<td rowspan="1" colspan="1">0.2485</td>
<td rowspan="1" colspan="1">0.075*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C21</td>
<td rowspan="1" colspan="1">−0.2239 (4)</td>
<td rowspan="1" colspan="1">0.5153 (2)</td>
<td rowspan="1" colspan="1">0.31101 (18)</td>
<td rowspan="1" colspan="1">0.0665 (6)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H21A</td>
<td rowspan="1" colspan="1">−0.1988</td>
<td rowspan="1" colspan="1">0.4303</td>
<td rowspan="1" colspan="1">0.3219</td>
<td rowspan="1" colspan="1">0.080*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C22</td>
<td rowspan="1" colspan="1">−0.1083 (3)</td>
<td rowspan="1" colspan="1">0.5782 (2)</td>
<td rowspan="1" colspan="1">0.33915 (16)</td>
<td rowspan="1" colspan="1">0.0551 (5)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H22A</td>
<td rowspan="1" colspan="1">−0.0063</td>
<td rowspan="1" colspan="1">0.5351</td>
<td rowspan="1" colspan="1">0.3690</td>
<td rowspan="1" colspan="1">0.066*</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e1234" sec-type="tablewrapadps"><label>5-(3-Phenylisothiazol-5-yl)-1,3,4-oxathiazol-2-one (I) </label>
<title>Atomic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e1246"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>11</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>22</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>33</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>12</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>13</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>23</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.0666 (4)</td>
<td rowspan="1" colspan="1">0.0408 (3)</td>
<td rowspan="1" colspan="1">0.0557 (3)</td>
<td rowspan="1" colspan="1">−0.0208 (2)</td>
<td rowspan="1" colspan="1">−0.0206 (2)</td>
<td rowspan="1" colspan="1">0.0026 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.0852 (11)</td>
<td rowspan="1" colspan="1">0.0496 (8)</td>
<td rowspan="1" colspan="1">0.0412 (8)</td>
<td rowspan="1" colspan="1">−0.0173 (7)</td>
<td rowspan="1" colspan="1">−0.0144 (7)</td>
<td rowspan="1" colspan="1">0.0018 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.0606 (11)</td>
<td rowspan="1" colspan="1">0.0476 (9)</td>
<td rowspan="1" colspan="1">0.0501 (9)</td>
<td rowspan="1" colspan="1">−0.0188 (8)</td>
<td rowspan="1" colspan="1">−0.0199 (8)</td>
<td rowspan="1" colspan="1">−0.0004 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.0459 (10)</td>
<td rowspan="1" colspan="1">0.0403 (9)</td>
<td rowspan="1" colspan="1">0.0471 (11)</td>
<td rowspan="1" colspan="1">−0.0130 (8)</td>
<td rowspan="1" colspan="1">−0.0093 (8)</td>
<td rowspan="1" colspan="1">0.0029 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">S2</td>
<td rowspan="1" colspan="1">0.0818 (4)</td>
<td rowspan="1" colspan="1">0.0563 (3)</td>
<td rowspan="1" colspan="1">0.0435 (3)</td>
<td rowspan="1" colspan="1">−0.0271 (3)</td>
<td rowspan="1" colspan="1">−0.0187 (3)</td>
<td rowspan="1" colspan="1">−0.0022 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.0543 (8)</td>
<td rowspan="1" colspan="1">0.0386 (7)</td>
<td rowspan="1" colspan="1">0.0404 (7)</td>
<td rowspan="1" colspan="1">−0.0131 (6)</td>
<td rowspan="1" colspan="1">−0.0127 (6)</td>
<td rowspan="1" colspan="1">0.0008 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.0673 (11)</td>
<td rowspan="1" colspan="1">0.0586 (10)</td>
<td rowspan="1" colspan="1">0.0407 (9)</td>
<td rowspan="1" colspan="1">−0.0234 (9)</td>
<td rowspan="1" colspan="1">−0.0148 (8)</td>
<td rowspan="1" colspan="1">0.0033 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.0387 (9)</td>
<td rowspan="1" colspan="1">0.0452 (10)</td>
<td rowspan="1" colspan="1">0.0420 (9)</td>
<td rowspan="1" colspan="1">−0.0133 (8)</td>
<td rowspan="1" colspan="1">−0.0108 (7)</td>
<td rowspan="1" colspan="1">−0.0007 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">S3</td>
<td rowspan="1" colspan="1">0.0545 (3)</td>
<td rowspan="1" colspan="1">0.0546 (3)</td>
<td rowspan="1" colspan="1">0.0554 (3)</td>
<td rowspan="1" colspan="1">−0.0224 (2)</td>
<td rowspan="1" colspan="1">−0.0255 (2)</td>
<td rowspan="1" colspan="1">0.0045 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3</td>
<td rowspan="1" colspan="1">0.0906 (13)</td>
<td rowspan="1" colspan="1">0.0567 (10)</td>
<td rowspan="1" colspan="1">0.1022 (14)</td>
<td rowspan="1" colspan="1">−0.0145 (9)</td>
<td rowspan="1" colspan="1">−0.0602 (11)</td>
<td rowspan="1" colspan="1">0.0188 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">N3</td>
<td rowspan="1" colspan="1">0.0500 (9)</td>
<td rowspan="1" colspan="1">0.0432 (8)</td>
<td rowspan="1" colspan="1">0.0505 (9)</td>
<td rowspan="1" colspan="1">−0.0191 (7)</td>
<td rowspan="1" colspan="1">−0.0202 (7)</td>
<td rowspan="1" colspan="1">0.0050 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.0358 (9)</td>
<td rowspan="1" colspan="1">0.0496 (10)</td>
<td rowspan="1" colspan="1">0.0399 (9)</td>
<td rowspan="1" colspan="1">−0.0125 (8)</td>
<td rowspan="1" colspan="1">−0.0105 (7)</td>
<td rowspan="1" colspan="1">0.0008 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">S4</td>
<td rowspan="1" colspan="1">0.0666 (3)</td>
<td rowspan="1" colspan="1">0.0398 (3)</td>
<td rowspan="1" colspan="1">0.0594 (3)</td>
<td rowspan="1" colspan="1">−0.0221 (2)</td>
<td rowspan="1" colspan="1">−0.0330 (3)</td>
<td rowspan="1" colspan="1">0.0094 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4</td>
<td rowspan="1" colspan="1">0.0534 (8)</td>
<td rowspan="1" colspan="1">0.0396 (7)</td>
<td rowspan="1" colspan="1">0.0538 (8)</td>
<td rowspan="1" colspan="1">−0.0150 (6)</td>
<td rowspan="1" colspan="1">−0.0225 (6)</td>
<td rowspan="1" colspan="1">0.0052 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">N4</td>
<td rowspan="1" colspan="1">0.0575 (10)</td>
<td rowspan="1" colspan="1">0.0443 (9)</td>
<td rowspan="1" colspan="1">0.0500 (9)</td>
<td rowspan="1" colspan="1">−0.0191 (7)</td>
<td rowspan="1" colspan="1">−0.0244 (7)</td>
<td rowspan="1" colspan="1">0.0048 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.0408 (10)</td>
<td rowspan="1" colspan="1">0.0469 (10)</td>
<td rowspan="1" colspan="1">0.0387 (9)</td>
<td rowspan="1" colspan="1">−0.0130 (8)</td>
<td rowspan="1" colspan="1">−0.0099 (7)</td>
<td rowspan="1" colspan="1">−0.0016 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.0322 (9)</td>
<td rowspan="1" colspan="1">0.0530 (10)</td>
<td rowspan="1" colspan="1">0.0381 (9)</td>
<td rowspan="1" colspan="1">−0.0136 (7)</td>
<td rowspan="1" colspan="1">−0.0070 (7)</td>
<td rowspan="1" colspan="1">−0.0002 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.0329 (9)</td>
<td rowspan="1" colspan="1">0.0512 (10)</td>
<td rowspan="1" colspan="1">0.0434 (9)</td>
<td rowspan="1" colspan="1">−0.0129 (7)</td>
<td rowspan="1" colspan="1">−0.0084 (7)</td>
<td rowspan="1" colspan="1">0.0039 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.0424 (10)</td>
<td rowspan="1" colspan="1">0.0569 (12)</td>
<td rowspan="1" colspan="1">0.0515 (11)</td>
<td rowspan="1" colspan="1">−0.0151 (9)</td>
<td rowspan="1" colspan="1">−0.0098 (8)</td>
<td rowspan="1" colspan="1">0.0013 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.0518 (12)</td>
<td rowspan="1" colspan="1">0.0536 (12)</td>
<td rowspan="1" colspan="1">0.0756 (15)</td>
<td rowspan="1" colspan="1">−0.0155 (10)</td>
<td rowspan="1" colspan="1">−0.0120 (11)</td>
<td rowspan="1" colspan="1">−0.0060 (10)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.0525 (13)</td>
<td rowspan="1" colspan="1">0.0535 (12)</td>
<td rowspan="1" colspan="1">0.0885 (17)</td>
<td rowspan="1" colspan="1">−0.0163 (10)</td>
<td rowspan="1" colspan="1">−0.0142 (11)</td>
<td rowspan="1" colspan="1">0.0128 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.0649 (15)</td>
<td rowspan="1" colspan="1">0.0684 (14)</td>
<td rowspan="1" colspan="1">0.0657 (14)</td>
<td rowspan="1" colspan="1">−0.0224 (11)</td>
<td rowspan="1" colspan="1">−0.0186 (11)</td>
<td rowspan="1" colspan="1">0.0252 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.0554 (12)</td>
<td rowspan="1" colspan="1">0.0638 (13)</td>
<td rowspan="1" colspan="1">0.0487 (11)</td>
<td rowspan="1" colspan="1">−0.0201 (10)</td>
<td rowspan="1" colspan="1">−0.0139 (9)</td>
<td rowspan="1" colspan="1">0.0073 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C12</td>
<td rowspan="1" colspan="1">0.0551 (12)</td>
<td rowspan="1" colspan="1">0.0499 (11)</td>
<td rowspan="1" colspan="1">0.0563 (12)</td>
<td rowspan="1" colspan="1">−0.0133 (9)</td>
<td rowspan="1" colspan="1">−0.0248 (9)</td>
<td rowspan="1" colspan="1">0.0056 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C13</td>
<td rowspan="1" colspan="1">0.0423 (10)</td>
<td rowspan="1" colspan="1">0.0378 (9)</td>
<td rowspan="1" colspan="1">0.0394 (9)</td>
<td rowspan="1" colspan="1">−0.0129 (7)</td>
<td rowspan="1" colspan="1">−0.0094 (7)</td>
<td rowspan="1" colspan="1">0.0012 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C14</td>
<td rowspan="1" colspan="1">0.0419 (10)</td>
<td rowspan="1" colspan="1">0.0391 (9)</td>
<td rowspan="1" colspan="1">0.0399 (9)</td>
<td rowspan="1" colspan="1">−0.0125 (7)</td>
<td rowspan="1" colspan="1">−0.0115 (7)</td>
<td rowspan="1" colspan="1">0.0016 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C15</td>
<td rowspan="1" colspan="1">0.0418 (10)</td>
<td rowspan="1" colspan="1">0.0377 (9)</td>
<td rowspan="1" colspan="1">0.0456 (10)</td>
<td rowspan="1" colspan="1">−0.0134 (7)</td>
<td rowspan="1" colspan="1">−0.0119 (8)</td>
<td rowspan="1" colspan="1">0.0033 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C16</td>
<td rowspan="1" colspan="1">0.0411 (10)</td>
<td rowspan="1" colspan="1">0.0416 (9)</td>
<td rowspan="1" colspan="1">0.0380 (9)</td>
<td rowspan="1" colspan="1">−0.0139 (7)</td>
<td rowspan="1" colspan="1">−0.0081 (7)</td>
<td rowspan="1" colspan="1">0.0002 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C17</td>
<td rowspan="1" colspan="1">0.0419 (10)</td>
<td rowspan="1" colspan="1">0.0496 (10)</td>
<td rowspan="1" colspan="1">0.0391 (9)</td>
<td rowspan="1" colspan="1">−0.0179 (8)</td>
<td rowspan="1" colspan="1">−0.0046 (7)</td>
<td rowspan="1" colspan="1">−0.0051 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C18</td>
<td rowspan="1" colspan="1">0.0532 (12)</td>
<td rowspan="1" colspan="1">0.0622 (12)</td>
<td rowspan="1" colspan="1">0.0491 (11)</td>
<td rowspan="1" colspan="1">−0.0252 (10)</td>
<td rowspan="1" colspan="1">−0.0164 (9)</td>
<td rowspan="1" colspan="1">0.0030 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1">C19</td>
<td rowspan="1" colspan="1">0.0531 (12)</td>
<td rowspan="1" colspan="1">0.0857 (16)</td>
<td rowspan="1" colspan="1">0.0502 (11)</td>
<td rowspan="1" colspan="1">−0.0313 (11)</td>
<td rowspan="1" colspan="1">−0.0171 (9)</td>
<td rowspan="1" colspan="1">−0.0032 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C20</td>
<td rowspan="1" colspan="1">0.0600 (14)</td>
<td rowspan="1" colspan="1">0.0822 (16)</td>
<td rowspan="1" colspan="1">0.0566 (12)</td>
<td rowspan="1" colspan="1">−0.0385 (12)</td>
<td rowspan="1" colspan="1">−0.0090 (10)</td>
<td rowspan="1" colspan="1">−0.0175 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C21</td>
<td rowspan="1" colspan="1">0.0719 (16)</td>
<td rowspan="1" colspan="1">0.0575 (13)</td>
<td rowspan="1" colspan="1">0.0790 (16)</td>
<td rowspan="1" colspan="1">−0.0310 (11)</td>
<td rowspan="1" colspan="1">−0.0153 (12)</td>
<td rowspan="1" colspan="1">−0.0107 (11)</td>
</tr>
<tr><td rowspan="1" colspan="1">C22</td>
<td rowspan="1" colspan="1">0.0540 (12)</td>
<td rowspan="1" colspan="1">0.0494 (11)</td>
<td rowspan="1" colspan="1">0.0671 (13)</td>
<td rowspan="1" colspan="1">−0.0195 (9)</td>
<td rowspan="1" colspan="1">−0.0170 (10)</td>
<td rowspan="1" colspan="1">−0.0051 (9)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e1951" sec-type="tablewrapgeomlong"><label>5-(3-Phenylisothiazol-5-yl)-1,3,4-oxathiazol-2-one (I) </label>
<title>Geometric parameters (Å, º)</title>
<table-wrap position="anchor" id="d1e1961"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="4"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">S1—N1</td>
<td rowspan="1" colspan="1">1.6845 (17)</td>
<td rowspan="1" colspan="1">C7—C8</td>
<td rowspan="1" colspan="1">1.380 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1</td>
<td rowspan="1" colspan="1">1.7616 (19)</td>
<td rowspan="1" colspan="1">C7—H7A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C1</td>
<td rowspan="1" colspan="1">1.185 (2)</td>
<td rowspan="1" colspan="1">C8—C9</td>
<td rowspan="1" colspan="1">1.380 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C2</td>
<td rowspan="1" colspan="1">1.271 (2)</td>
<td rowspan="1" colspan="1">C8—H8A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—O2</td>
<td rowspan="1" colspan="1">1.391 (2)</td>
<td rowspan="1" colspan="1">C9—C10</td>
<td rowspan="1" colspan="1">1.376 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">S2—N2</td>
<td rowspan="1" colspan="1">1.6406 (18)</td>
<td rowspan="1" colspan="1">C9—H9A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">S2—C3</td>
<td rowspan="1" colspan="1">1.7071 (18)</td>
<td rowspan="1" colspan="1">C10—C11</td>
<td rowspan="1" colspan="1">1.382 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—C2</td>
<td rowspan="1" colspan="1">1.364 (2)</td>
<td rowspan="1" colspan="1">C10—H10A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C5</td>
<td rowspan="1" colspan="1">1.327 (2)</td>
<td rowspan="1" colspan="1">C11—H11A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3</td>
<td rowspan="1" colspan="1">1.449 (3)</td>
<td rowspan="1" colspan="1">C13—C14</td>
<td rowspan="1" colspan="1">1.447 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">S3—N3</td>
<td rowspan="1" colspan="1">1.6790 (16)</td>
<td rowspan="1" colspan="1">C14—C15</td>
<td rowspan="1" colspan="1">1.365 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">S3—C12</td>
<td rowspan="1" colspan="1">1.746 (2)</td>
<td rowspan="1" colspan="1">C15—C16</td>
<td rowspan="1" colspan="1">1.417 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O3—C12</td>
<td rowspan="1" colspan="1">1.187 (3)</td>
<td rowspan="1" colspan="1">C15—H15A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N3—C13</td>
<td rowspan="1" colspan="1">1.278 (2)</td>
<td rowspan="1" colspan="1">C16—C17</td>
<td rowspan="1" colspan="1">1.479 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4</td>
<td rowspan="1" colspan="1">1.361 (3)</td>
<td rowspan="1" colspan="1">C17—C22</td>
<td rowspan="1" colspan="1">1.386 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">S4—N4</td>
<td rowspan="1" colspan="1">1.6457 (17)</td>
<td rowspan="1" colspan="1">C17—C18</td>
<td rowspan="1" colspan="1">1.387 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">S4—C14</td>
<td rowspan="1" colspan="1">1.7084 (18)</td>
<td rowspan="1" colspan="1">C18—C19</td>
<td rowspan="1" colspan="1">1.384 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—C13</td>
<td rowspan="1" colspan="1">1.361 (2)</td>
<td rowspan="1" colspan="1">C18—H18A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">O4—C12</td>
<td rowspan="1" colspan="1">1.385 (2)</td>
<td rowspan="1" colspan="1">C19—C20</td>
<td rowspan="1" colspan="1">1.380 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">N4—C16</td>
<td rowspan="1" colspan="1">1.329 (2)</td>
<td rowspan="1" colspan="1">C19—H19A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5</td>
<td rowspan="1" colspan="1">1.417 (3)</td>
<td rowspan="1" colspan="1">C20—C21</td>
<td rowspan="1" colspan="1">1.371 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—H4B</td>
<td rowspan="1" colspan="1">0.9300</td>
<td rowspan="1" colspan="1">C20—H20A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C6</td>
<td rowspan="1" colspan="1">1.476 (3)</td>
<td rowspan="1" colspan="1">C21—C22</td>
<td rowspan="1" colspan="1">1.386 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C7</td>
<td rowspan="1" colspan="1">1.390 (3)</td>
<td rowspan="1" colspan="1">C21—H21A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C11</td>
<td rowspan="1" colspan="1">1.398 (3)</td>
<td rowspan="1" colspan="1">C22—H22A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1—S1—C1</td>
<td rowspan="1" colspan="1">93.13 (8)</td>
<td rowspan="1" colspan="1">C9—C10—H10A</td>
<td rowspan="1" colspan="1">119.6</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—N1—S1</td>
<td rowspan="1" colspan="1">109.43 (14)</td>
<td rowspan="1" colspan="1">C11—C10—H10A</td>
<td rowspan="1" colspan="1">119.6</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C1—O2</td>
<td rowspan="1" colspan="1">122.21 (17)</td>
<td rowspan="1" colspan="1">C10—C11—C6</td>
<td rowspan="1" colspan="1">120.3 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C1—S1</td>
<td rowspan="1" colspan="1">131.23 (16)</td>
<td rowspan="1" colspan="1">C10—C11—H11A</td>
<td rowspan="1" colspan="1">119.9</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—C1—S1</td>
<td rowspan="1" colspan="1">106.56 (13)</td>
<td rowspan="1" colspan="1">C6—C11—H11A</td>
<td rowspan="1" colspan="1">119.9</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—S2—C3</td>
<td rowspan="1" colspan="1">94.78 (9)</td>
<td rowspan="1" colspan="1">O3—C12—O4</td>
<td rowspan="1" colspan="1">122.3 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—O2—C1</td>
<td rowspan="1" colspan="1">111.28 (14)</td>
<td rowspan="1" colspan="1">O3—C12—S3</td>
<td rowspan="1" colspan="1">130.15 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—N2—S2</td>
<td rowspan="1" colspan="1">110.54 (13)</td>
<td rowspan="1" colspan="1">O4—C12—S3</td>
<td rowspan="1" colspan="1">107.58 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C2—O2</td>
<td rowspan="1" colspan="1">119.58 (17)</td>
<td rowspan="1" colspan="1">N3—C13—O4</td>
<td rowspan="1" colspan="1">120.27 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C2—C3</td>
<td rowspan="1" colspan="1">124.86 (17)</td>
<td rowspan="1" colspan="1">N3—C13—C14</td>
<td rowspan="1" colspan="1">123.90 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—C2—C3</td>
<td rowspan="1" colspan="1">115.55 (16)</td>
<td rowspan="1" colspan="1">O4—C13—C14</td>
<td rowspan="1" colspan="1">115.82 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">N3—S3—C12</td>
<td rowspan="1" colspan="1">93.31 (9)</td>
<td rowspan="1" colspan="1">C15—C14—C13</td>
<td rowspan="1" colspan="1">128.92 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">C13—N3—S3</td>
<td rowspan="1" colspan="1">108.63 (13)</td>
<td rowspan="1" colspan="1">C15—C14—S4</td>
<td rowspan="1" colspan="1">109.41 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—C2</td>
<td rowspan="1" colspan="1">129.89 (17)</td>
<td rowspan="1" colspan="1">C13—C14—S4</td>
<td rowspan="1" colspan="1">121.66 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—S2</td>
<td rowspan="1" colspan="1">108.82 (14)</td>
<td rowspan="1" colspan="1">C14—C15—C16</td>
<td rowspan="1" colspan="1">110.62 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—C3—S2</td>
<td rowspan="1" colspan="1">121.28 (14)</td>
<td rowspan="1" colspan="1">C14—C15—H15A</td>
<td rowspan="1" colspan="1">124.7</td>
</tr>
<tr><td rowspan="1" colspan="1">N4—S4—C14</td>
<td rowspan="1" colspan="1">94.50 (9)</td>
<td rowspan="1" colspan="1">C16—C15—H15A</td>
<td rowspan="1" colspan="1">124.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C13—O4—C12</td>
<td rowspan="1" colspan="1">110.20 (15)</td>
<td rowspan="1" colspan="1">N4—C16—C15</td>
<td rowspan="1" colspan="1">115.12 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C16—N4—S4</td>
<td rowspan="1" colspan="1">110.35 (13)</td>
<td rowspan="1" colspan="1">N4—C16—C17</td>
<td rowspan="1" colspan="1">119.36 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—C5</td>
<td rowspan="1" colspan="1">111.36 (16)</td>
<td rowspan="1" colspan="1">C15—C16—C17</td>
<td rowspan="1" colspan="1">125.51 (16)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—H4B</td>
<td rowspan="1" colspan="1">124.3</td>
<td rowspan="1" colspan="1">C22—C17—C18</td>
<td rowspan="1" colspan="1">118.80 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C4—H4B</td>
<td rowspan="1" colspan="1">124.3</td>
<td rowspan="1" colspan="1">C22—C17—C16</td>
<td rowspan="1" colspan="1">120.93 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C5—C4</td>
<td rowspan="1" colspan="1">114.50 (17)</td>
<td rowspan="1" colspan="1">C18—C17—C16</td>
<td rowspan="1" colspan="1">120.26 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C5—C6</td>
<td rowspan="1" colspan="1">119.40 (16)</td>
<td rowspan="1" colspan="1">C19—C18—C17</td>
<td rowspan="1" colspan="1">120.2 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C5—C6</td>
<td rowspan="1" colspan="1">126.10 (16)</td>
<td rowspan="1" colspan="1">C19—C18—H18A</td>
<td rowspan="1" colspan="1">119.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—C6—C11</td>
<td rowspan="1" colspan="1">118.40 (19)</td>
<td rowspan="1" colspan="1">C17—C18—H18A</td>
<td rowspan="1" colspan="1">119.9</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—C6—C5</td>
<td rowspan="1" colspan="1">121.30 (17)</td>
<td rowspan="1" colspan="1">C20—C19—C18</td>
<td rowspan="1" colspan="1">120.6 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11—C6—C5</td>
<td rowspan="1" colspan="1">120.29 (18)</td>
<td rowspan="1" colspan="1">C20—C19—H19A</td>
<td rowspan="1" colspan="1">119.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C7—C6</td>
<td rowspan="1" colspan="1">120.7 (2)</td>
<td rowspan="1" colspan="1">C18—C19—H19A</td>
<td rowspan="1" colspan="1">119.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C7—H7A</td>
<td rowspan="1" colspan="1">119.7</td>
<td rowspan="1" colspan="1">C21—C20—C19</td>
<td rowspan="1" colspan="1">119.5 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6—C7—H7A</td>
<td rowspan="1" colspan="1">119.7</td>
<td rowspan="1" colspan="1">C21—C20—H20A</td>
<td rowspan="1" colspan="1">120.2</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—C8—C9</td>
<td rowspan="1" colspan="1">120.5 (2)</td>
<td rowspan="1" colspan="1">C19—C20—H20A</td>
<td rowspan="1" colspan="1">120.2</td>
</tr>
<tr><td rowspan="1" colspan="1">C7—C8—H8A</td>
<td rowspan="1" colspan="1">119.7</td>
<td rowspan="1" colspan="1">C20—C21—C22</td>
<td rowspan="1" colspan="1">120.3 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C8—H8A</td>
<td rowspan="1" colspan="1">119.7</td>
<td rowspan="1" colspan="1">C20—C21—H21A</td>
<td rowspan="1" colspan="1">119.8</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C9—C8</td>
<td rowspan="1" colspan="1">119.4 (2)</td>
<td rowspan="1" colspan="1">C22—C21—H21A</td>
<td rowspan="1" colspan="1">119.8</td>
</tr>
<tr><td rowspan="1" colspan="1">C10—C9—H9A</td>
<td rowspan="1" colspan="1">120.3</td>
<td rowspan="1" colspan="1">C17—C22—C21</td>
<td rowspan="1" colspan="1">120.6 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8—C9—H9A</td>
<td rowspan="1" colspan="1">120.3</td>
<td rowspan="1" colspan="1">C17—C22—H22A</td>
<td rowspan="1" colspan="1">119.7</td>
</tr>
<tr><td rowspan="1" colspan="1">C9—C10—C11</td>
<td rowspan="1" colspan="1">120.7 (2)</td>
<td rowspan="1" colspan="1">C21—C22—H22A</td>
<td rowspan="1" colspan="1">119.7</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e2558" sec-type="tablewrapcrystaldatalong"><label>5-(3-Phenylisothiazol-4-yl)-1,3,4-oxathiazol-2-one (II) </label>
<title>Crystal data</title>
<table-wrap position="anchor" id="d1e2567"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">C<sub>11</sub>
H<sub>6</sub>
N<sub>2</sub>
O<sub>2</sub>
S<sub>2</sub>
</td>
<td rowspan="1" colspan="1"><italic>F</italic>
(000) = 536</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>M</italic>
<italic><sub>r</sub>
</italic>
= 262.30</td>
<td rowspan="1" colspan="1"><italic>D</italic>
<sub>x</sub>
= 1.602 Mg m<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>
2<sub>1</sub>
/<italic>c</italic>
</td>
<td rowspan="1" colspan="1">Mo <italic>K</italic>
α radiation, λ = 0.71073 Å</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>a</italic>
= 9.7202 (6) Å</td>
<td rowspan="1" colspan="1">Cell parameters from 6714 reflections</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>b</italic>
= 9.9723 (6) Å</td>
<td rowspan="1" colspan="1">θ = 2.7–28.3°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>c</italic>
= 11.2165 (7) Å</td>
<td rowspan="1" colspan="1">µ = 0.48 mm<sup>−</sup>
<sup>1</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">β = 90.399 (1)°</td>
<td rowspan="1" colspan="1"><italic>T</italic>
= 296 K</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>V</italic>
= 1087.22 (12) Å<sup>3</sup>
</td>
<td rowspan="1" colspan="1">Block, colorless</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>Z</italic>
= 4</td>
<td rowspan="1" colspan="1">0.48 × 0.43 × 0.37 mm</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e2687" sec-type="tablewrapdatacollectionlong"><label>5-(3-Phenylisothiazol-4-yl)-1,3,4-oxathiazol-2-one (II) </label>
<title>Data collection</title>
<table-wrap position="anchor" id="d1e2696"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Bruker APEXII CCD diffractometer</td>
<td rowspan="1" colspan="1">2228 reflections with <italic>I</italic>
> 2σ(<italic>I</italic>
)</td>
</tr>
<tr><td rowspan="1" colspan="1">φ and ω scans</td>
<td rowspan="1" colspan="1"><italic>R</italic>
<sub>int</sub>
= 0.017</td>
</tr>
<tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (SADABS; Bruker, 2008)</td>
<td rowspan="1" colspan="1">θ<sub>max</sub>
= 27.0°, θ<sub>min</sub>
= 2.9°</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>T</italic>
<sub>min</sub>
= 0.719, <italic>T</italic>
<sub>max</sub>
= 0.837</td>
<td rowspan="1" colspan="1"><italic>h</italic>
= −12→12</td>
</tr>
<tr><td rowspan="1" colspan="1">8041 measured reflections</td>
<td rowspan="1" colspan="1"><italic>k</italic>
= −12→9</td>
</tr>
<tr><td rowspan="1" colspan="1">2362 independent reflections</td>
<td rowspan="1" colspan="1"><italic>l</italic>
= −14→14</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e2796" sec-type="tablewraprefinementdatalong"><label>5-(3-Phenylisothiazol-4-yl)-1,3,4-oxathiazol-2-one (II) </label>
<title>Refinement</title>
<table-wrap position="anchor" id="d1e2805"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic>
<sup>2</sup>
</td>
<td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td>
</tr>
<tr><td rowspan="1" colspan="1">Least-squares matrix: full</td>
<td rowspan="1" colspan="1">H-atom parameters constrained</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
> 2σ(<italic>F</italic>
<sup>2</sup>
)] = 0.030</td>
<td rowspan="1" colspan="1"><italic>w</italic>
= 1/[σ<sup>2</sup>
(<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
) + (0.0465<italic>P</italic>
)<sup>2</sup>
+ 0.4061<italic>P</italic>
] where <italic>P</italic>
= (<italic>F</italic>
<sub>o</sub>
<sup>2</sup>
+ 2<italic>F</italic>
<sub>c</sub>
<sup>2</sup>
)/3</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
) = 0.083</td>
<td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub>
= 0.001</td>
</tr>
<tr><td rowspan="1" colspan="1"><italic>S</italic>
= 1.02</td>
<td rowspan="1" colspan="1">Δρ<sub>max</sub>
= 0.37 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">2362 reflections</td>
<td rowspan="1" colspan="1">Δρ<sub>min</sub>
= −0.28 e Å<sup>−</sup>
<sup>3</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">155 parameters</td>
<td rowspan="1" colspan="1">Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc<sup>*</sup>
=kFc[1+0.001xFc<sup>2</sup>
λ<sup>3</sup>
/sin(2θ)]<sup>-1/4</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">0 restraints</td>
<td rowspan="1" colspan="1">Extinction coefficient: 0.018 (2)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e2967" sec-type="specialdetails"><label>5-(3-Phenylisothiazol-4-yl)-1,3,4-oxathiazol-2-one (II) </label>
<title>Special details</title>
<table-wrap position="anchor" id="d1e2977"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e2986" sec-type="tablewrapcoords"><label>5-(3-Phenylisothiazol-4-yl)-1,3,4-oxathiazol-2-one (II) </label>
<title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e2998"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>x</italic>
</td>
<td rowspan="1" colspan="1"><italic>y</italic>
</td>
<td rowspan="1" colspan="1"><italic>z</italic>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sub>iso</sub>
*/<italic>U</italic>
<sub>eq</sub>
</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S2</td>
<td rowspan="1" colspan="1">0.45224 (4)</td>
<td rowspan="1" colspan="1">0.17168 (4)</td>
<td rowspan="1" colspan="1">0.50567 (3)</td>
<td rowspan="1" colspan="1">0.04262 (13)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.88687 (4)</td>
<td rowspan="1" colspan="1">0.63218 (4)</td>
<td rowspan="1" colspan="1">0.59213 (4)</td>
<td rowspan="1" colspan="1">0.04650 (14)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.65815 (9)</td>
<td rowspan="1" colspan="1">0.53305 (10)</td>
<td rowspan="1" colspan="1">0.65111 (8)</td>
<td rowspan="1" colspan="1">0.0330 (2)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.74809 (14)</td>
<td rowspan="1" colspan="1">0.63165 (15)</td>
<td rowspan="1" colspan="1">0.69017 (12)</td>
<td rowspan="1" colspan="1">0.0365 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.62185 (13)</td>
<td rowspan="1" colspan="1">0.35992 (13)</td>
<td rowspan="1" colspan="1">0.50912 (11)</td>
<td rowspan="1" colspan="1">0.0288 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.72696 (12)</td>
<td rowspan="1" colspan="1">0.69783 (14)</td>
<td rowspan="1" colspan="1">0.77664 (11)</td>
<td rowspan="1" colspan="1">0.0542 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.70630 (13)</td>
<td rowspan="1" colspan="1">0.47087 (13)</td>
<td rowspan="1" colspan="1">0.55025 (10)</td>
<td rowspan="1" colspan="1">0.0288 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.55493 (14)</td>
<td rowspan="1" colspan="1">0.18187 (13)</td>
<td rowspan="1" colspan="1">0.38899 (11)</td>
<td rowspan="1" colspan="1">0.0427 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.82008 (12)</td>
<td rowspan="1" colspan="1">0.51010 (13)</td>
<td rowspan="1" colspan="1">0.50596 (10)</td>
<td rowspan="1" colspan="1">0.0395 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.51836 (13)</td>
<td rowspan="1" colspan="1">0.30589 (14)</td>
<td rowspan="1" colspan="1">0.57667 (12)</td>
<td rowspan="1" colspan="1">0.0330 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H4</td>
<td rowspan="1" colspan="1">0.4894</td>
<td rowspan="1" colspan="1">0.3384</td>
<td rowspan="1" colspan="1">0.6501</td>
<td rowspan="1" colspan="1">0.040*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.63936 (13)</td>
<td rowspan="1" colspan="1">0.28477 (14)</td>
<td rowspan="1" colspan="1">0.40146 (11)</td>
<td rowspan="1" colspan="1">0.0325 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.74116 (14)</td>
<td rowspan="1" colspan="1">0.31005 (14)</td>
<td rowspan="1" colspan="1">0.30578 (11)</td>
<td rowspan="1" colspan="1">0.0337 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.83741 (15)</td>
<td rowspan="1" colspan="1">0.21201 (15)</td>
<td rowspan="1" colspan="1">0.27851 (13)</td>
<td rowspan="1" colspan="1">0.0386 (3)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H11A</td>
<td rowspan="1" colspan="1">0.8384</td>
<td rowspan="1" colspan="1">0.1317</td>
<td rowspan="1" colspan="1">0.3206</td>
<td rowspan="1" colspan="1">0.046*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.73957 (18)</td>
<td rowspan="1" colspan="1">0.42883 (17)</td>
<td rowspan="1" colspan="1">0.24153 (14)</td>
<td rowspan="1" colspan="1">0.0472 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H7A</td>
<td rowspan="1" colspan="1">0.6757</td>
<td rowspan="1" colspan="1">0.4951</td>
<td rowspan="1" colspan="1">0.2595</td>
<td rowspan="1" colspan="1">0.057*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.93225 (15)</td>
<td rowspan="1" colspan="1">0.23383 (18)</td>
<td rowspan="1" colspan="1">0.18830 (14)</td>
<td rowspan="1" colspan="1">0.0465 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H10A</td>
<td rowspan="1" colspan="1">0.9976</td>
<td rowspan="1" colspan="1">0.1687</td>
<td rowspan="1" colspan="1">0.1710</td>
<td rowspan="1" colspan="1">0.056*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.92952 (19)</td>
<td rowspan="1" colspan="1">0.3518 (2)</td>
<td rowspan="1" colspan="1">0.12467 (15)</td>
<td rowspan="1" colspan="1">0.0530 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H9A</td>
<td rowspan="1" colspan="1">0.9927</td>
<td rowspan="1" colspan="1">0.3662</td>
<td rowspan="1" colspan="1">0.0641</td>
<td rowspan="1" colspan="1">0.064*</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.8330 (2)</td>
<td rowspan="1" colspan="1">0.4488 (2)</td>
<td rowspan="1" colspan="1">0.15076 (15)</td>
<td rowspan="1" colspan="1">0.0560 (4)</td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">H8A</td>
<td rowspan="1" colspan="1">0.8307</td>
<td rowspan="1" colspan="1">0.5280</td>
<td rowspan="1" colspan="1">0.1070</td>
<td rowspan="1" colspan="1">0.067*</td>
<td rowspan="1" colspan="1"></td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e3300" sec-type="tablewrapadps"><label>5-(3-Phenylisothiazol-4-yl)-1,3,4-oxathiazol-2-one (II) </label>
<title>Atomic displacement parameters (Å<sup>2</sup>
)</title>
<table-wrap position="anchor" id="d1e3312"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>11</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>22</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>33</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>12</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>13</sup>
</td>
<td rowspan="1" colspan="1"><italic>U</italic>
<sup>23</sup>
</td>
</tr>
<tr><td rowspan="1" colspan="1">S2</td>
<td rowspan="1" colspan="1">0.0448 (2)</td>
<td rowspan="1" colspan="1">0.0372 (2)</td>
<td rowspan="1" colspan="1">0.0460 (2)</td>
<td rowspan="1" colspan="1">−0.01130 (15)</td>
<td rowspan="1" colspan="1">0.00795 (16)</td>
<td rowspan="1" colspan="1">−0.00051 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1</td>
<td rowspan="1" colspan="1">0.0414 (2)</td>
<td rowspan="1" colspan="1">0.0518 (3)</td>
<td rowspan="1" colspan="1">0.0465 (2)</td>
<td rowspan="1" colspan="1">−0.01591 (16)</td>
<td rowspan="1" colspan="1">0.01521 (16)</td>
<td rowspan="1" colspan="1">−0.01786 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1</td>
<td rowspan="1" colspan="1">0.0314 (4)</td>
<td rowspan="1" colspan="1">0.0366 (5)</td>
<td rowspan="1" colspan="1">0.0311 (4)</td>
<td rowspan="1" colspan="1">−0.0004 (4)</td>
<td rowspan="1" colspan="1">0.0070 (3)</td>
<td rowspan="1" colspan="1">−0.0061 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1</td>
<td rowspan="1" colspan="1">0.0343 (6)</td>
<td rowspan="1" colspan="1">0.0385 (7)</td>
<td rowspan="1" colspan="1">0.0368 (7)</td>
<td rowspan="1" colspan="1">0.0007 (5)</td>
<td rowspan="1" colspan="1">0.0045 (5)</td>
<td rowspan="1" colspan="1">−0.0079 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3</td>
<td rowspan="1" colspan="1">0.0290 (6)</td>
<td rowspan="1" colspan="1">0.0297 (6)</td>
<td rowspan="1" colspan="1">0.0277 (6)</td>
<td rowspan="1" colspan="1">0.0022 (5)</td>
<td rowspan="1" colspan="1">0.0018 (4)</td>
<td rowspan="1" colspan="1">0.0015 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2</td>
<td rowspan="1" colspan="1">0.0487 (6)</td>
<td rowspan="1" colspan="1">0.0632 (7)</td>
<td rowspan="1" colspan="1">0.0508 (6)</td>
<td rowspan="1" colspan="1">−0.0034 (5)</td>
<td rowspan="1" colspan="1">0.0123 (5)</td>
<td rowspan="1" colspan="1">−0.0286 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2</td>
<td rowspan="1" colspan="1">0.0309 (6)</td>
<td rowspan="1" colspan="1">0.0307 (6)</td>
<td rowspan="1" colspan="1">0.0248 (5)</td>
<td rowspan="1" colspan="1">0.0034 (5)</td>
<td rowspan="1" colspan="1">0.0032 (4)</td>
<td rowspan="1" colspan="1">−0.0011 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2</td>
<td rowspan="1" colspan="1">0.0485 (7)</td>
<td rowspan="1" colspan="1">0.0387 (7)</td>
<td rowspan="1" colspan="1">0.0409 (6)</td>
<td rowspan="1" colspan="1">−0.0091 (5)</td>
<td rowspan="1" colspan="1">0.0072 (5)</td>
<td rowspan="1" colspan="1">−0.0070 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1</td>
<td rowspan="1" colspan="1">0.0380 (6)</td>
<td rowspan="1" colspan="1">0.0447 (7)</td>
<td rowspan="1" colspan="1">0.0359 (6)</td>
<td rowspan="1" colspan="1">−0.0089 (5)</td>
<td rowspan="1" colspan="1">0.0103 (5)</td>
<td rowspan="1" colspan="1">−0.0122 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C4</td>
<td rowspan="1" colspan="1">0.0341 (6)</td>
<td rowspan="1" colspan="1">0.0325 (6)</td>
<td rowspan="1" colspan="1">0.0325 (6)</td>
<td rowspan="1" colspan="1">0.0005 (5)</td>
<td rowspan="1" colspan="1">0.0038 (5)</td>
<td rowspan="1" colspan="1">0.0025 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5</td>
<td rowspan="1" colspan="1">0.0345 (6)</td>
<td rowspan="1" colspan="1">0.0321 (6)</td>
<td rowspan="1" colspan="1">0.0310 (6)</td>
<td rowspan="1" colspan="1">0.0003 (5)</td>
<td rowspan="1" colspan="1">0.0017 (5)</td>
<td rowspan="1" colspan="1">−0.0014 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C6</td>
<td rowspan="1" colspan="1">0.0359 (7)</td>
<td rowspan="1" colspan="1">0.0375 (7)</td>
<td rowspan="1" colspan="1">0.0277 (6)</td>
<td rowspan="1" colspan="1">−0.0039 (5)</td>
<td rowspan="1" colspan="1">0.0018 (5)</td>
<td rowspan="1" colspan="1">−0.0069 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1">C11</td>
<td rowspan="1" colspan="1">0.0390 (7)</td>
<td rowspan="1" colspan="1">0.0394 (7)</td>
<td rowspan="1" colspan="1">0.0375 (7)</td>
<td rowspan="1" colspan="1">−0.0018 (6)</td>
<td rowspan="1" colspan="1">−0.0013 (5)</td>
<td rowspan="1" colspan="1">−0.0091 (6)</td>
</tr>
<tr><td rowspan="1" colspan="1">C7</td>
<td rowspan="1" colspan="1">0.0556 (9)</td>
<td rowspan="1" colspan="1">0.0439 (9)</td>
<td rowspan="1" colspan="1">0.0422 (8)</td>
<td rowspan="1" colspan="1">0.0062 (7)</td>
<td rowspan="1" colspan="1">0.0132 (7)</td>
<td rowspan="1" colspan="1">0.0012 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C10</td>
<td rowspan="1" colspan="1">0.0381 (7)</td>
<td rowspan="1" colspan="1">0.0568 (10)</td>
<td rowspan="1" colspan="1">0.0448 (8)</td>
<td rowspan="1" colspan="1">−0.0001 (7)</td>
<td rowspan="1" colspan="1">0.0056 (6)</td>
<td rowspan="1" colspan="1">−0.0179 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1">C9</td>
<td rowspan="1" colspan="1">0.0525 (9)</td>
<td rowspan="1" colspan="1">0.0679 (11)</td>
<td rowspan="1" colspan="1">0.0389 (8)</td>
<td rowspan="1" colspan="1">−0.0095 (8)</td>
<td rowspan="1" colspan="1">0.0164 (7)</td>
<td rowspan="1" colspan="1">−0.0097 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1">C8</td>
<td rowspan="1" colspan="1">0.0709 (11)</td>
<td rowspan="1" colspan="1">0.0543 (10)</td>
<td rowspan="1" colspan="1">0.0432 (8)</td>
<td rowspan="1" colspan="1">−0.0021 (8)</td>
<td rowspan="1" colspan="1">0.0166 (8)</td>
<td rowspan="1" colspan="1">0.0065 (7)</td>
</tr>
</table>
</table-wrap>
</sec>
<sec id="d1e3652" sec-type="tablewrapgeomlong"><label>5-(3-Phenylisothiazol-4-yl)-1,3,4-oxathiazol-2-one (II) </label>
<title>Geometric parameters (Å, º)</title>
<table-wrap position="anchor" id="d1e3662"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="4"><col span="1"></col>
<col span="1"></col>
<col span="1"></col>
<col span="1"></col>
</colgroup>
<tr><td rowspan="1" colspan="1">S2—N2</td>
<td rowspan="1" colspan="1">1.6546 (13)</td>
<td rowspan="1" colspan="1">C5—C6</td>
<td rowspan="1" colspan="1">1.4864 (18)</td>
</tr>
<tr><td rowspan="1" colspan="1">S2—C4</td>
<td rowspan="1" colspan="1">1.6827 (14)</td>
<td rowspan="1" colspan="1">C6—C7</td>
<td rowspan="1" colspan="1">1.386 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—N1</td>
<td rowspan="1" colspan="1">1.6820 (12)</td>
<td rowspan="1" colspan="1">C6—C11</td>
<td rowspan="1" colspan="1">1.389 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">S1—C1</td>
<td rowspan="1" colspan="1">1.7463 (14)</td>
<td rowspan="1" colspan="1">C11—C10</td>
<td rowspan="1" colspan="1">1.391 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C2</td>
<td rowspan="1" colspan="1">1.3750 (14)</td>
<td rowspan="1" colspan="1">C11—H11A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C1</td>
<td rowspan="1" colspan="1">1.3849 (17)</td>
<td rowspan="1" colspan="1">C7—C8</td>
<td rowspan="1" colspan="1">1.383 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1">C1—O2</td>
<td rowspan="1" colspan="1">1.1921 (17)</td>
<td rowspan="1" colspan="1">C7—H7A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4</td>
<td rowspan="1" colspan="1">1.3737 (18)</td>
<td rowspan="1" colspan="1">C10—C9</td>
<td rowspan="1" colspan="1">1.376 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C5</td>
<td rowspan="1" colspan="1">1.4324 (17)</td>
<td rowspan="1" colspan="1">C10—H10A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C2</td>
<td rowspan="1" colspan="1">1.4511 (18)</td>
<td rowspan="1" colspan="1">C9—C8</td>
<td rowspan="1" colspan="1">1.380 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—N1</td>
<td rowspan="1" colspan="1">1.2770 (17)</td>
<td rowspan="1" colspan="1">C9—H9A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C5</td>
<td rowspan="1" colspan="1">1.3208 (18)</td>
<td rowspan="1" colspan="1">C8—H8A</td>
<td rowspan="1" colspan="1">0.9300</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—H4</td>
<td rowspan="1" colspan="1">0.9300</td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
<td rowspan="1" colspan="1"></td>
</tr>
<tr><td rowspan="1" colspan="1">N2—S2—C4</td>
<td rowspan="1" colspan="1">95.45 (6)</td>
<td rowspan="1" colspan="1">C3—C5—C6</td>
<td rowspan="1" colspan="1">127.12 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—S1—C1</td>
<td rowspan="1" colspan="1">93.61 (6)</td>
<td rowspan="1" colspan="1">C7—C6—C11</td>
<td rowspan="1" colspan="1">119.48 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—O1—C1</td>
<td rowspan="1" colspan="1">111.27 (10)</td>
<td rowspan="1" colspan="1">C7—C6—C5</td>
<td rowspan="1" colspan="1">121.01 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—C1—O1</td>
<td rowspan="1" colspan="1">122.58 (13)</td>
<td rowspan="1" colspan="1">C11—C6—C5</td>
<td rowspan="1" colspan="1">119.50 (13)</td>
</tr>
<tr><td rowspan="1" colspan="1">O2—C1—S1</td>
<td rowspan="1" colspan="1">130.46 (12)</td>
<td rowspan="1" colspan="1">C6—C11—C10</td>
<td rowspan="1" colspan="1">120.07 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C1—S1</td>
<td rowspan="1" colspan="1">106.96 (9)</td>
<td rowspan="1" colspan="1">C6—C11—H11A</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—C5</td>
<td rowspan="1" colspan="1">110.58 (12)</td>
<td rowspan="1" colspan="1">C10—C11—H11A</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C4—C3—C2</td>
<td rowspan="1" colspan="1">122.58 (12)</td>
<td rowspan="1" colspan="1">C8—C7—C6</td>
<td rowspan="1" colspan="1">120.03 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—C3—C2</td>
<td rowspan="1" colspan="1">126.64 (11)</td>
<td rowspan="1" colspan="1">C8—C7—H7A</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C2—O1</td>
<td rowspan="1" colspan="1">118.86 (12)</td>
<td rowspan="1" colspan="1">C6—C7—H7A</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">N1—C2—C3</td>
<td rowspan="1" colspan="1">126.82 (12)</td>
<td rowspan="1" colspan="1">C9—C10—C11</td>
<td rowspan="1" colspan="1">120.04 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">O1—C2—C3</td>
<td rowspan="1" colspan="1">114.23 (11)</td>
<td rowspan="1" colspan="1">C9—C10—H10A</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C5—N2—S2</td>
<td rowspan="1" colspan="1">109.98 (10)</td>
<td rowspan="1" colspan="1">C11—C10—H10A</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C2—N1—S1</td>
<td rowspan="1" colspan="1">109.27 (9)</td>
<td rowspan="1" colspan="1">C10—C9—C8</td>
<td rowspan="1" colspan="1">119.98 (15)</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—S2</td>
<td rowspan="1" colspan="1">109.25 (10)</td>
<td rowspan="1" colspan="1">C10—C9—H9A</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">C3—C4—H4</td>
<td rowspan="1" colspan="1">125.4</td>
<td rowspan="1" colspan="1">C8—C9—H9A</td>
<td rowspan="1" colspan="1">120.0</td>
</tr>
<tr><td rowspan="1" colspan="1">S2—C4—H4</td>
<td rowspan="1" colspan="1">125.4</td>
<td rowspan="1" colspan="1">C9—C8—C7</td>
<td rowspan="1" colspan="1">120.40 (17)</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C5—C3</td>
<td rowspan="1" colspan="1">114.74 (12)</td>
<td rowspan="1" colspan="1">C9—C8—H8A</td>
<td rowspan="1" colspan="1">119.8</td>
</tr>
<tr><td rowspan="1" colspan="1">N2—C5—C6</td>
<td rowspan="1" colspan="1">118.14 (12)</td>
<td rowspan="1" colspan="1">C7—C8—H8A</td>
<td rowspan="1" colspan="1">119.8</td>
</tr>
</table>
</table-wrap>
</sec>
</app>
</app-group>
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<floats-group><fig id="fig1" orientation="portrait" position="float"><label>Figure 1</label>
<caption><p>The molecular structure of (I)<xref ref-type="chem" rid="scheme1"></xref>
, showing 50% probability displacement ellipsoids.</p>
</caption>
<graphic xlink:href="e-73-01726-fig1"></graphic>
</fig>
<fig id="fig2" orientation="portrait" position="float"><label>Figure 2</label>
<caption><p>The molecular structure of (II)<xref ref-type="chem" rid="scheme1"></xref>
, showing 50% probability displacement ellipsoids.</p>
</caption>
<graphic xlink:href="e-73-01726-fig2"></graphic>
</fig>
<fig id="fig3" orientation="portrait" position="float"><label>Figure 3</label>
<caption><p>A packing diagram of (I)<xref ref-type="chem" rid="scheme1"></xref>
showing π–π stacking parallel to the <italic>a</italic>
-axis direction (top). Co-planar paired head-to-head molecules [green lines, S⋯N distance of 3.086 (2) Å] and paired molecules separated by out-of-plane contacts [blue lines, S⋯N distance of 3.072 (2) Å], violet lines S⋯O distance of 3.089 (1) Å].</p>
</caption>
<graphic xlink:href="e-73-01726-fig3"></graphic>
</fig>
<fig id="fig4" orientation="portrait" position="float"><label>Figure 4</label>
<caption><p>A packing diagram of (II)<xref ref-type="chem" rid="scheme1"></xref>
within the unit cell showing molecular pairs linked by S⋯O contacts of 3.020 (1) Å.</p>
</caption>
<graphic xlink:href="e-73-01726-fig4"></graphic>
</fig>
<fig id="fig5" orientation="portrait" position="float"><label>Figure 5</label>
<caption><p>A photograph of crystals of (I)<xref ref-type="chem" rid="scheme1"></xref>
(5 × 5 mm background grid).</p>
</caption>
<graphic xlink:href="e-73-01726-fig5"></graphic>
</fig>
<fig id="fig6" orientation="portrait" position="float"><label>Figure 6</label>
<caption><p>A photograph of crystals of (II)<xref ref-type="chem" rid="scheme1"></xref>
(5 × 5 mm background grid).</p>
</caption>
<graphic xlink:href="e-73-01726-fig6"></graphic>
</fig>
<table-wrap id="table1" orientation="portrait" position="float"><label>Table 1</label>
<caption><title>Experimental details</title>
</caption>
<table frame="hsides" rules="groups"><thead valign="top"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top"> </th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top">(I)</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top">(II)</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="3" align="left" valign="top">Crystal data</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Chemical formula</td>
<td rowspan="1" colspan="1" align="left" valign="top">C<sub>11</sub>
H<sub>6</sub>
N<sub>2</sub>
O<sub>2</sub>
S<sub>2</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">C<sub>11</sub>
H<sub>6</sub>
N<sub>2</sub>
O<sub>2</sub>
S<sub>2</sub>
</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>M</italic>
<sub>r</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">262.30</td>
<td rowspan="1" colspan="1" align="left" valign="top">262.30</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal system, space group</td>
<td rowspan="1" colspan="1" align="left" valign="top">Triclinic, <italic>P</italic>
<inline-formula><inline-graphic xlink:href="e-73-01726-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">Monoclinic, <italic>P</italic>
2<sub>1</sub>
/<italic>c</italic>
</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Temperature (K)</td>
<td rowspan="1" colspan="1" align="left" valign="top">296</td>
<td rowspan="1" colspan="1" align="left" valign="top">296</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>a</italic>
, <italic>b</italic>
, <italic>c</italic>
(Å)</td>
<td rowspan="1" colspan="1" align="left" valign="top">7.2739 (7), 11.2713 (11), 14.6909 (15)</td>
<td rowspan="1" colspan="1" align="left" valign="top">9.7202 (6), 9.9723 (6), 11.2165 (7)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">α, β, γ (°)</td>
<td rowspan="1" colspan="1" align="left" valign="top">87.562 (1), 78.341 (1), 71.624 (1)</td>
<td rowspan="1" colspan="1" align="left" valign="top">90, 90.399 (1), 90</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>V</italic>
(Å<sup>3</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1119.16 (19)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1087.22 (12)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>Z</italic>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">4</td>
<td rowspan="1" colspan="1" align="left" valign="top">4</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Radiation type</td>
<td rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>
α</td>
<td rowspan="1" colspan="1" align="left" valign="top">Mo <italic>K</italic>
α</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">μ (mm<sup>−1</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.46</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.48</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Crystal size (mm)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.49 × 0.25 × 0.14</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.48 × 0.43 × 0.37</td>
</tr>
<tr><td rowspan="1" colspan="3" align="left" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="3" align="left" valign="top">Data collection</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Diffractometer</td>
<td rowspan="1" colspan="1" align="left" valign="top">Bruker APEXII CCD</td>
<td rowspan="1" colspan="1" align="left" valign="top">Bruker APEXII CCD</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Absorption correction</td>
<td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>SADABS</italic>
; Bruker, 2008<xref ref-type="bibr" rid="bb5"> ▸</xref>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>SADABS</italic>
; Bruker, 2008<xref ref-type="bibr" rid="bb5"> ▸</xref>
)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>T</italic>
<sub>min</sub>
, <italic>T</italic>
<sub>max</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.804, 0.936</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.719, 0.837</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of measured, independent and observed [<italic>I</italic>
> 2σ(<italic>I</italic>
)] reflections</td>
<td rowspan="1" colspan="1" align="left" valign="top">7476, 3862, 3485</td>
<td rowspan="1" colspan="1" align="left" valign="top">8041, 2362, 2228</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic>
<sub>int</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.015</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.017</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">(sin θ/λ)<sub>max</sub>
(Å<sup>−1</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.595</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.639</td>
</tr>
<tr><td rowspan="1" colspan="3" align="left" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="3" align="left" valign="top">Refinement</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"><italic>R</italic>
[<italic>F</italic>
<sup>2</sup>
> 2σ(<italic>F</italic>
<sup>2</sup>
)], <italic>wR</italic>
(<italic>F</italic>
<sup>2</sup>
), <italic>S</italic>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.031, 0.106, 1.04</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.030, 0.083, 1.02</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of reflections</td>
<td rowspan="1" colspan="1" align="left" valign="top">3862</td>
<td rowspan="1" colspan="1" align="left" valign="top">2362</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of parameters</td>
<td rowspan="1" colspan="1" align="left" valign="top">308</td>
<td rowspan="1" colspan="1" align="left" valign="top">155</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">H-atom treatment</td>
<td rowspan="1" colspan="1" align="left" valign="top">H-atom parameters constrained</td>
<td rowspan="1" colspan="1" align="left" valign="top">H-atom parameters constrained</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Δρ<sub>max</sub>
, Δρ<sub>min</sub>
(e Å<sup>−3</sup>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.33, −0.23</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.37, −0.28</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Computer programs: <italic>APEX2</italic>
and <italic>SAINT</italic>
(Bruker, 2008<xref ref-type="bibr" rid="bb5"> ▸</xref>
), <italic>SHELXS97</italic>
(Sheldrick, 2008<xref ref-type="bibr" rid="bb27"> ▸</xref>
) and <italic>SHELXL2014</italic>
(Sheldrick, 2015<xref ref-type="bibr" rid="bb30"> ▸</xref>
).</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
</record>
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