Synthesis, mol-ecular and crystal structure of 1-(1,2-di-hydro-phthalazin-1-yl-idene)-2-[1-(thio-phen-2-yl)ethyl-idene]hydrazine.
Identifieur interne : 000632 ( PubMed/Curation ); précédent : 000631; suivant : 000633Synthesis, mol-ecular and crystal structure of 1-(1,2-di-hydro-phthalazin-1-yl-idene)-2-[1-(thio-phen-2-yl)ethyl-idene]hydrazine.
Auteurs : Felicite Majoumo-Mbe [Cameroun] ; Emmanuel Ngwang Nfor [Cameroun] ; Patrice Kenfack Tsobnang [Cameroun] ; Valoise Brenda Nguepmeni Eloundou [Cameroun] ; Joseph Ngwain Yong [Cameroun] ; Ikome Iris Efeti [Cameroun]Source :
- Acta crystallographica. Section E, Crystallographic communications [ 2056-9890 ] ; 2019.
Abstract
The title compound, C14H12N4S, was synthesized by the condensation reaction of hydralazine and 2-acetyl-thio-phene and during the reaction, a proton transfer from the imino nitro-gen atom to one of the endocylic nitro-gen atoms occurred. The compound crystallizes in the monoclinic crystal system with two independent mol-ecules (mol-ecules 1 and 2) in the asymmetric unit. In each mol-ecule, there is a slight difference in the orientation of the thio-phene ring with respect to phthalazine ring system, mol-ecule 1 showing a dihedral angle of 42.51 (1)° compared to 8.48 (1)° in mol-ecule 2. This implies an r.m.s deviation of 0.428 (1) Å between the two mol-ecules for the 19 non-H atoms. The two independent mol-ecules are connected via two N-H⋯N hydrogen bonds, forming dimers which inter-act by two bifurcated π-π stacking inter-actions to build tetra-meric motifs. The latter are packed in the ac plane via weak C-H⋯π inter-actions and along the b axis via C-H ⋯N and C-H⋯π inter-actions. This results a three-dimensional architecture with a tilted herringbone packing mode.
DOI: 10.1107/S2056989019000732
PubMed: 30800461
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wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</nlm:affiliation><country xml:lang="fr">Cameroun</country><wicri:regionArea>Department of Chemistry, University of Buea, PO Box 63 Buea</wicri:regionArea></affiliation></author><author><name sortKey="Ngwang Nfor, Emmanuel" sort="Ngwang Nfor, Emmanuel" uniqKey="Ngwang Nfor E" first="Emmanuel" last="Ngwang Nfor">Emmanuel Ngwang Nfor</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</nlm:affiliation><country xml:lang="fr">Cameroun</country><wicri:regionArea>Department of Chemistry, University of Buea, PO Box 63 Buea</wicri:regionArea></affiliation></author><author><name sortKey="Kenfack Tsobnang, Patrice" sort="Kenfack Tsobnang, Patrice" uniqKey="Kenfack Tsobnang P" first="Patrice" last="Kenfack Tsobnang">Patrice Kenfack Tsobnang</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Dschang, PO Box 67, Dschang, Cameroon.</nlm:affiliation><country xml:lang="fr">Cameroun</country><wicri:regionArea>Department of Chemistry, University of Dschang, PO Box 67, Dschang</wicri:regionArea></affiliation></author><author><name sortKey="Nguepmeni Eloundou, Valoise Brenda" sort="Nguepmeni Eloundou, Valoise Brenda" uniqKey="Nguepmeni Eloundou V" first="Valoise Brenda" last="Nguepmeni Eloundou">Valoise Brenda Nguepmeni Eloundou</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Dschang, PO Box 67, Dschang, Cameroon.</nlm:affiliation><country xml:lang="fr">Cameroun</country><wicri:regionArea>Department of Chemistry, University of Dschang, PO Box 67, Dschang</wicri:regionArea></affiliation></author><author><name sortKey="Ngwain Yong, Joseph" sort="Ngwain Yong, Joseph" uniqKey="Ngwain Yong J" first="Joseph" last="Ngwain Yong">Joseph Ngwain Yong</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</nlm:affiliation><country xml:lang="fr">Cameroun</country><wicri:regionArea>Department of Chemistry, University of Buea, PO Box 63 Buea</wicri:regionArea></affiliation></author><author><name sortKey="Iris Efeti, Ikome" sort="Iris Efeti, Ikome" uniqKey="Iris Efeti I" first="Ikome" last="Iris Efeti">Ikome Iris Efeti</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</nlm:affiliation><country xml:lang="fr">Cameroun</country><wicri:regionArea>Department of Chemistry, University of Buea, PO Box 63 Buea</wicri:regionArea></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 title compound, C<sub>14</sub>H<sub>12</sub>N<sub>4</sub>S, was synthesized by the condensation reaction of hydralazine and 2-acetyl-thio-phene and during the reaction, a proton transfer from the imino nitro-gen atom to one of the endocylic nitro-gen atoms occurred. The compound crystallizes in the monoclinic crystal system with two independent mol-ecules (mol-ecules 1 and 2) in the asymmetric unit. In each mol-ecule, there is a slight difference in the orientation of the thio-phene ring with respect to phthalazine ring system, mol-ecule 1 showing a dihedral angle of 42.51 (1)° compared to 8.48 (1)° in mol-ecule 2. This implies an r.m.s deviation of 0.428 (1) Å between the two mol-ecules for the 19 non-H atoms. The two independent mol-ecules are connected <i>via</i> two N-H⋯N hydrogen bonds, forming dimers which inter-act by two bifurcated π-π stacking inter-actions to build tetra-meric motifs. The latter are packed in the <i>ac</i> plane <i>via</i> weak C-H⋯π inter-actions and along the <i>b</i> axis <i>via</i> C-H ⋯N and C-H⋯π inter-actions. This results a three-dimensional architecture with a tilted herringbone packing mode.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">30800461</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>Synthesis, mol-ecular and crystal structure of 1-(1,2-di-hydro-phthalazin-1-yl-idene)-2-[1-(thio-phen-2-yl)ethyl-idene]hydrazine.</ArticleTitle><Pagination><MedlinePgn>251-254</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1107/S2056989019000732</ELocationID><Abstract><AbstractText>The title compound, C<sub>14</sub>H<sub>12</sub>N<sub>4</sub>S, was synthesized by the condensation reaction of hydralazine and 2-acetyl-thio-phene and during the reaction, a proton transfer from the imino nitro-gen atom to one of the endocylic nitro-gen atoms occurred. The compound crystallizes in the monoclinic crystal system with two independent mol-ecules (mol-ecules 1 and 2) in the asymmetric unit. In each mol-ecule, there is a slight difference in the orientation of the thio-phene ring with respect to phthalazine ring system, mol-ecule 1 showing a dihedral angle of 42.51 (1)° compared to 8.48 (1)° in mol-ecule 2. This implies an r.m.s deviation of 0.428 (1) Å between the two mol-ecules for the 19 non-H atoms. The two independent mol-ecules are connected <i>via</i> two N-H⋯N hydrogen bonds, forming dimers which inter-act by two bifurcated π-π stacking inter-actions to build tetra-meric motifs. The latter are packed in the <i>ac</i> plane <i>via</i> weak C-H⋯π inter-actions and along the <i>b</i> axis <i>via</i> C-H ⋯N and C-H⋯π inter-actions. This results a three-dimensional architecture with a tilted herringbone packing mode.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Majoumo-Mbe</LastName><ForeName>Felicite</ForeName><Initials>F</Initials><AffiliationInfo><Affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ngwang Nfor</LastName><ForeName>Emmanuel</ForeName><Initials>E</Initials><AffiliationInfo><Affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kenfack Tsobnang</LastName><ForeName>Patrice</ForeName><Initials>P</Initials><Identifier Source="ORCID">https://orcid.org/0000-0002-1888-0099</Identifier><AffiliationInfo><Affiliation>Department of Chemistry, University of Dschang, PO Box 67, Dschang, Cameroon.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Nguepmeni Eloundou</LastName><ForeName>Valoise Brenda</ForeName><Initials>VB</Initials><AffiliationInfo><Affiliation>Department of Chemistry, University of Dschang, PO Box 67, Dschang, Cameroon.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ngwain Yong</LastName><ForeName>Joseph</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Iris Efeti</LastName><ForeName>Ikome</ForeName><Initials>I</Initials><Identifier Source="ORCID">https://orcid.org/0000-0002-5296-0092</Identifier><AffiliationInfo><Affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</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>22</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Acta Crystallogr E Crystallogr Commun</MedlineTA><NlmUniqueID>101648987</NlmUniqueID></MedlineJournalInfo><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">2-Acetylthiophene-1-phthalazinylhydrazone</Keyword><Keyword MajorTopicYN="N">C—H⋯π interactions</Keyword><Keyword MajorTopicYN="N">bifurcated stacking interactions</Keyword><Keyword MajorTopicYN="N">chevron-shaped motifs</Keyword><Keyword MajorTopicYN="N">co-planar rings</Keyword><Keyword MajorTopicYN="N">condensation reaction</Keyword><Keyword MajorTopicYN="N">crystal structure</Keyword><Keyword MajorTopicYN="N">tetramers</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2018</Year><Month>12</Month><Day>13</Day></PubMedPubDate><PubMedPubDate 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