Hydrogen-bonded mol-ecular salts of reduced benzo-thia-zole derivatives with carboxyl-ates: a robust (8) supra-molecular motif (even when disordered).
Identifieur interne : 000633 ( PubMed/Corpus ); précédent : 000632; suivant : 000634Hydrogen-bonded mol-ecular salts of reduced benzo-thia-zole derivatives with carboxyl-ates: a robust (8) supra-molecular motif (even when disordered).
Auteurs : Mohammed A E. Shaibah ; Belakavadi K. Sagar ; Hemmige S. Yathirajan ; David B. Cordes ; Alexandra M Z. Slawin ; William T A. HarrisonSource :
- Acta crystallographica. Section E, Crystallographic communications [ 2056-9890 ] ; 2019.
Abstract
The syntheses and structures of five mol-ecular salts of protonated 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine (C11H19N2S+) with different deprotonated carb-oxy-lic acids (4-methyl-benzoic acid, 4-bromo-benzoic acid, 3,5-di-nitro-benzoic acid, fumaric acid and succinic acid) are reported, namely 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-methyl-benzoate, C11H19N2S+·C8H7O2-, (I), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-bromo-benzoate, C11H19N2S+·C7H4BrO2-, (II), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 3,5-di-nitro-benzoate, C11H19N2S+·C7H3N2O6-, (III), bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) fumarate, 2C11H19N2S+·C4H2O42-,(IV), and the 1:1 co-crystal of bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) succinate and 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium hydrogen succin-ate 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine, 1.5C11H19N2S+·0.5C4H4O42-·0.5C4H5O4-. 0.5C11H18N2S, (V). In every case, the cation protonation occurs at the N atom of the thia-zole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methyl-ene groups are disordered over two sets of sites). The C-N bond lengths of the nominal -NH+=C-NH2 fragment of the cation are indistinguishable, indicating a significant contribution of the -NH-C=N+H2 resonance form to the structure. The packing for (I)-(V) features a robust local R22(8) loop motif in which the cation forms two near-linear N-H⋯O hydrogen bonds from the N+-H group and syn H atom of the amine group to the carboxyl-ate group of an adjacent anion [(V) shows disorder of one of these bonds over N-H⋯O and N⋯H-O contributors but the same R22(8) loop results for both disorder components]. The anti H atom of the -NH2 group also forms an N-H⋯O hydrogen bond, which results in [001] chains in (I) and (II), isolated centrosymmetric tetra-mers in (III) and [100] chains in (IV) and (V). Hirshfeld fingerprint plots and contact percentages for the different types of contacts of the cations are discussed.
DOI: 10.1107/S2056989018018224
PubMed: 30800445
Links to Exploration step
pubmed:30800445Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Hydrogen-bonded mol-ecular salts of reduced benzo-thia-zole derivatives with carboxyl-ates: a robust (8) supra-molecular motif (even when disordered).</title>
<author><name sortKey="Shaibah, Mohammed A E" sort="Shaibah, Mohammed A E" uniqKey="Shaibah M" first="Mohammed A E" last="Shaibah">Mohammed A E. Shaibah</name>
<affiliation><nlm:affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Sagar, Belakavadi K" sort="Sagar, Belakavadi K" uniqKey="Sagar B" first="Belakavadi K" last="Sagar">Belakavadi K. Sagar</name>
<affiliation><nlm:affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Yathirajan, Hemmige S" sort="Yathirajan, Hemmige S" uniqKey="Yathirajan H" first="Hemmige S" last="Yathirajan">Hemmige S. Yathirajan</name>
<affiliation><nlm:affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Cordes, David B" sort="Cordes, David B" uniqKey="Cordes D" first="David B" last="Cordes">David B. Cordes</name>
<affiliation><nlm:affiliation>School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Slawin, Alexandra M Z" sort="Slawin, Alexandra M Z" uniqKey="Slawin A" first="Alexandra M Z" last="Slawin">Alexandra M Z. Slawin</name>
<affiliation><nlm:affiliation>School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Harrison, William T A" sort="Harrison, William T A" uniqKey="Harrison W" first="William T A" last="Harrison">William T A. Harrison</name>
<affiliation><nlm:affiliation>Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.</nlm:affiliation>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PubMed</idno>
<date when="2019">2019</date>
<idno type="RBID">pubmed:30800445</idno>
<idno type="pmid">30800445</idno>
<idno type="doi">10.1107/S2056989018018224</idno>
<idno type="wicri:Area/PubMed/Corpus">000633</idno>
<idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000633</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en">Hydrogen-bonded mol-ecular salts of reduced benzo-thia-zole derivatives with carboxyl-ates: a robust (8) supra-molecular motif (even when disordered).</title>
<author><name sortKey="Shaibah, Mohammed A E" sort="Shaibah, Mohammed A E" uniqKey="Shaibah M" first="Mohammed A E" last="Shaibah">Mohammed A E. Shaibah</name>
<affiliation><nlm:affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Sagar, Belakavadi K" sort="Sagar, Belakavadi K" uniqKey="Sagar B" first="Belakavadi K" last="Sagar">Belakavadi K. Sagar</name>
<affiliation><nlm:affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Yathirajan, Hemmige S" sort="Yathirajan, Hemmige S" uniqKey="Yathirajan H" first="Hemmige S" last="Yathirajan">Hemmige S. Yathirajan</name>
<affiliation><nlm:affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Cordes, David B" sort="Cordes, David B" uniqKey="Cordes D" first="David B" last="Cordes">David B. Cordes</name>
<affiliation><nlm:affiliation>School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Slawin, Alexandra M Z" sort="Slawin, Alexandra M Z" uniqKey="Slawin A" first="Alexandra M Z" last="Slawin">Alexandra M Z. Slawin</name>
<affiliation><nlm:affiliation>School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Harrison, William T A" sort="Harrison, William T A" uniqKey="Harrison W" first="William T A" last="Harrison">William T A. Harrison</name>
<affiliation><nlm:affiliation>Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.</nlm:affiliation>
</affiliation>
</author>
</analytic>
<series><title level="j">Acta crystallographica. Section E, Crystallographic communications</title>
<idno type="ISSN">2056-9890</idno>
<imprint><date when="2019" type="published">2019</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">The syntheses and structures of five mol-ecular salts of protonated 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
) with different deprotonated carb-oxy-lic acids (4-methyl-benzoic acid, 4-bromo-benzoic acid, 3,5-di-nitro-benzoic acid, fumaric acid and succinic acid) are reported, namely 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-methyl-benzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>8</sub>
H<sub>7</sub>
O<sub>2</sub>
<sup>-</sup>
, (I), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-bromo-benzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>4</sub>
BrO<sub>2</sub>
<sup>-</sup>
, (II), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 3,5-di-nitro-benzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>3</sub>
N<sub>2</sub>
O<sub>6</sub>
<sup>-</sup>
, (III), bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) fumarate, 2C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>4</sub>
H<sub>2</sub>
O<sub>4</sub>
<sup>2-</sup>
,(IV), and the 1:1 co-crystal of bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) succinate and 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium hydrogen succin-ate 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine, 1.5C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·0.5C<sub>4</sub>
H<sub>4</sub>
O<sub>4</sub>
<sup>2-</sup>
·0.5C<sub>4</sub>
H<sub>5</sub>
O<sub>4</sub>
<sup>-</sup>
. 0.5C<sub>11</sub>
H<sub>18</sub>
N<sub>2</sub>
S, (V). In every case, the cation protonation occurs at the N atom of the thia-zole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methyl-ene groups are disordered over two sets of sites). The C-N bond lengths of the nominal -NH<sup>+</sup>
=C-NH<sub>2</sub>
fragment of the cation are indistinguishable, indicating a significant contribution of the -NH-C=N<sup>+</sup>
H<sub>2</sub>
resonance form to the structure. The packing for (I)-(V) features a robust local <i>R</i>
<sub>2</sub>
<sup>2</sup>
(8) loop motif in which the cation forms two near-linear N-H⋯O hydrogen bonds from the N<sup>+</sup>
-H group and <i>syn</i>
H atom of the amine group to the carboxyl-ate group of an adjacent anion [(V) shows disorder of one of these bonds over N-H⋯O and N⋯H-O contributors but the same <i>R</i>
<sub>2</sub>
<sup>2</sup>
(8) loop results for both disorder components]. The <i>anti</i>
H atom of the -NH<sub>2</sub>
group also forms an N-H⋯O hydrogen bond, which results in [001] chains in (I) and (II), isolated centrosymmetric tetra-mers in (III) and [100] chains in (IV) and (V). Hirshfeld fingerprint plots and contact percentages for the different types of contacts of the cations are discussed.</div>
</front>
</TEI>
<pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">30800445</PMID>
<DateRevised><Year>2020</Year>
<Month>02</Month>
<Day>25</Day>
</DateRevised>
<Article PubModel="Electronic-eCollection"><Journal><ISSN IssnType="Print">2056-9890</ISSN>
<JournalIssue CitedMedium="Print"><Volume>75</Volume>
<Issue>Pt 2</Issue>
<PubDate><Year>2019</Year>
<Month>Feb</Month>
<Day>01</Day>
</PubDate>
</JournalIssue>
<Title>Acta crystallographica. Section E, Crystallographic communications</Title>
<ISOAbbreviation>Acta Crystallogr E Crystallogr Commun</ISOAbbreviation>
</Journal>
<ArticleTitle>Hydrogen-bonded mol-ecular salts of reduced benzo-thia-zole derivatives with carboxyl-ates: a robust (8) supra-molecular motif (even when disordered).</ArticleTitle>
<Pagination><MedlinePgn>167-174</MedlinePgn>
</Pagination>
<ELocationID EIdType="doi" ValidYN="Y">10.1107/S2056989018018224</ELocationID>
<Abstract><AbstractText>The syntheses and structures of five mol-ecular salts of protonated 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine (C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
) with different deprotonated carb-oxy-lic acids (4-methyl-benzoic acid, 4-bromo-benzoic acid, 3,5-di-nitro-benzoic acid, fumaric acid and succinic acid) are reported, namely 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-methyl-benzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>8</sub>
H<sub>7</sub>
O<sub>2</sub>
<sup>-</sup>
, (I), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-bromo-benzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>4</sub>
BrO<sub>2</sub>
<sup>-</sup>
, (II), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 3,5-di-nitro-benzoate, C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>7</sub>
H<sub>3</sub>
N<sub>2</sub>
O<sub>6</sub>
<sup>-</sup>
, (III), bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) fumarate, 2C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·C<sub>4</sub>
H<sub>2</sub>
O<sub>4</sub>
<sup>2-</sup>
,(IV), and the 1:1 co-crystal of bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) succinate and 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium hydrogen succin-ate 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine, 1.5C<sub>11</sub>
H<sub>19</sub>
N<sub>2</sub>
S<sup>+</sup>
·0.5C<sub>4</sub>
H<sub>4</sub>
O<sub>4</sub>
<sup>2-</sup>
·0.5C<sub>4</sub>
H<sub>5</sub>
O<sub>4</sub>
<sup>-</sup>
. 0.5C<sub>11</sub>
H<sub>18</sub>
N<sub>2</sub>
S, (V). In every case, the cation protonation occurs at the N atom of the thia-zole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methyl-ene groups are disordered over two sets of sites). The C-N bond lengths of the nominal -NH<sup>+</sup>
=C-NH<sub>2</sub>
fragment of the cation are indistinguishable, indicating a significant contribution of the -NH-C=N<sup>+</sup>
H<sub>2</sub>
resonance form to the structure. The packing for (I)-(V) features a robust local <i>R</i>
<sub>2</sub>
<sup>2</sup>
(8) loop motif in which the cation forms two near-linear N-H⋯O hydrogen bonds from the N<sup>+</sup>
-H group and <i>syn</i>
H atom of the amine group to the carboxyl-ate group of an adjacent anion [(V) shows disorder of one of these bonds over N-H⋯O and N⋯H-O contributors but the same <i>R</i>
<sub>2</sub>
<sup>2</sup>
(8) loop results for both disorder components]. The <i>anti</i>
H atom of the -NH<sub>2</sub>
group also forms an N-H⋯O hydrogen bond, which results in [001] chains in (I) and (II), isolated centrosymmetric tetra-mers in (III) and [100] chains in (IV) and (V). Hirshfeld fingerprint plots and contact percentages for the different types of contacts of the cations are discussed.</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Shaibah</LastName>
<ForeName>Mohammed A E</ForeName>
<Initials>MAE</Initials>
<AffiliationInfo><Affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Sagar</LastName>
<ForeName>Belakavadi K</ForeName>
<Initials>BK</Initials>
<AffiliationInfo><Affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Yathirajan</LastName>
<ForeName>Hemmige S</ForeName>
<Initials>HS</Initials>
<Identifier Source="ORCID">https://orcid.org/0000-0001-9039-0273</Identifier>
<AffiliationInfo><Affiliation>Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Cordes</LastName>
<ForeName>David B</ForeName>
<Initials>DB</Initials>
<Identifier Source="ORCID">https://orcid.org/0000-0002-5366-9168</Identifier>
<AffiliationInfo><Affiliation>School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Slawin</LastName>
<ForeName>Alexandra M Z</ForeName>
<Initials>AMZ</Initials>
<AffiliationInfo><Affiliation>School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Harrison</LastName>
<ForeName>William T A</ForeName>
<Initials>WTA</Initials>
<Identifier Source="ORCID">https://orcid.org/0000-0003-2253-4866</Identifier>
<AffiliationInfo><Affiliation>Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland.</Affiliation>
</AffiliationInfo>
</Author>
</AuthorList>
<Language>eng</Language>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic"><Year>2019</Year>
<Month>01</Month>
<Day>08</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo><Country>England</Country>
<MedlineTA>Acta Crystallogr E Crystallogr Commun</MedlineTA>
<NlmUniqueID>101648987</NlmUniqueID>
</MedlineJournalInfo>
<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">benzothiazole</Keyword>
<Keyword MajorTopicYN="N">crystal structure</Keyword>
<Keyword MajorTopicYN="N">hydrogen bond</Keyword>
<Keyword MajorTopicYN="N">molecular salt</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2018</Year>
<Month>12</Month>
<Day>10</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="accepted"><Year>2018</Year>
<Month>12</Month>
<Day>21</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2019</Year>
<Month>2</Month>
<Day>26</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed"><Year>2019</Year>
<Month>2</Month>
<Day>26</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2019</Year>
<Month>2</Month>
<Day>26</Day>
<Hour>6</Hour>
<Minute>1</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>epublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">30800445</ArticleId>
<ArticleId IdType="doi">10.1107/S2056989018018224</ArticleId>
<ArticleId IdType="pii">mw2140</ArticleId>
<ArticleId IdType="pmc">PMC6362640</ArticleId>
</ArticleIdList>
<ReferenceList><Reference><Citation>J Med Chem. 1991 Sep;34(9):2736-46</Citation>
<ArticleIdList><ArticleId IdType="pubmed">1680195</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Acta Crystallogr A. 2008 Jan;64(Pt 1):112-22</Citation>
<ArticleIdList><ArticleId IdType="pubmed">18156677</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Chem Commun (Camb). 2007 Oct 7;(37):3814-6</Citation>
<ArticleIdList><ArticleId IdType="pubmed">18217656</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Phys Chem A. 2011 Apr 14;115(14):3154-66</Citation>
<ArticleIdList><ArticleId IdType="pubmed">21428393</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Inorg Chem. 2011 Jun 6;50(11):4732-41</Citation>
<ArticleIdList><ArticleId IdType="pubmed">21520903</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Acta Crystallogr B Struct Sci Cryst Eng Mater. 2013 Jun;69(Pt 3):249-59</Citation>
<ArticleIdList><ArticleId IdType="pubmed">23719469</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Acta Crystallogr C Struct Chem. 2015 Jan;71(Pt 1):3-8</Citation>
<ArticleIdList><ArticleId IdType="pubmed">25567568</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Acta Crystallogr B Struct Sci Cryst Eng Mater. 2015 Apr;71(Pt 2):228-34</Citation>
<ArticleIdList><ArticleId IdType="pubmed">25827376</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Acta Crystallogr B Struct Sci Cryst Eng Mater. 2016 Apr;72(Pt 2):171-9</Citation>
<ArticleIdList><ArticleId IdType="pubmed">27048719</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Can J Neurol Sci. 2018 Jul;45(4):375-404</Citation>
<ArticleIdList><ArticleId IdType="pubmed">29747716</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>ACS Med Chem Lett. 2018 May 30;9(6):552-556</Citation>
<ArticleIdList><ArticleId IdType="pubmed">29937981</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 1987 Mar;30(3):494-8</Citation>
<ArticleIdList><ArticleId IdType="pubmed">3820220</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
</PubmedData>
</pubmed>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Sante/explor/MersV1/Data/PubMed/Corpus
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000633 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/PubMed/Corpus/biblio.hfd -nk 000633 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Sante |area= MersV1 |flux= PubMed |étape= Corpus |type= RBID |clé= pubmed:30800445 |texte= Hydrogen-bonded mol-ecular salts of reduced benzo-thia-zole derivatives with carboxyl-ates: a robust (8) supra-molecular motif (even when disordered). }}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/PubMed/Corpus/RBID.i -Sk "pubmed:30800445" \ | HfdSelect -Kh $EXPLOR_AREA/Data/PubMed/Corpus/biblio.hfd \ | NlmPubMed2Wicri -a MersV1
![]() | This area was generated with Dilib version V0.6.33. | ![]() |