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/Corpus ); 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 ; Emmanuel Ngwang Nfor ; Patrice Kenfack Tsobnang ; Valoise Brenda Nguepmeni Eloundou ; Joseph Ngwain Yong ; Ikome Iris EfetiSource :
- 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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pubmed:30800461Le document en format XML
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<author><name sortKey="Majoumo Mbe, Felicite" sort="Majoumo Mbe, Felicite" uniqKey="Majoumo Mbe F" first="Felicite" last="Majoumo-Mbe">Felicite Majoumo-Mbe</name>
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<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>
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<author><name sortKey="Ngwain Yong, Joseph" sort="Ngwain Yong, Joseph" uniqKey="Ngwain Yong J" first="Joseph" last="Ngwain Yong">Joseph Ngwain Yong</name>
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<author><name sortKey="Iris Efeti, Ikome" sort="Iris Efeti, Ikome" uniqKey="Iris Efeti I" first="Ikome" last="Iris Efeti">Ikome Iris Efeti</name>
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<sourceDesc><biblStruct><analytic><title xml:lang="en">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.</title>
<author><name sortKey="Majoumo Mbe, Felicite" sort="Majoumo Mbe, Felicite" uniqKey="Majoumo Mbe F" first="Felicite" last="Majoumo-Mbe">Felicite Majoumo-Mbe</name>
<affiliation><nlm:affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</nlm:affiliation>
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<author><name sortKey="Ngwang Nfor, Emmanuel" sort="Ngwang Nfor, Emmanuel" uniqKey="Ngwang Nfor E" first="Emmanuel" last="Ngwang Nfor">Emmanuel Ngwang Nfor</name>
<affiliation><nlm:affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</nlm:affiliation>
</affiliation>
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<author><name sortKey="Kenfack Tsobnang, Patrice" sort="Kenfack Tsobnang, Patrice" uniqKey="Kenfack Tsobnang P" first="Patrice" last="Kenfack Tsobnang">Patrice Kenfack Tsobnang</name>
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<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><nlm:affiliation>Department of Chemistry, University of Dschang, PO Box 67, Dschang, Cameroon.</nlm:affiliation>
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<author><name sortKey="Ngwain Yong, Joseph" sort="Ngwain Yong, Joseph" uniqKey="Ngwain Yong J" first="Joseph" last="Ngwain Yong">Joseph Ngwain Yong</name>
<affiliation><nlm:affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</nlm:affiliation>
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<author><name sortKey="Iris Efeti, Ikome" sort="Iris Efeti, Ikome" uniqKey="Iris Efeti I" first="Ikome" last="Iris Efeti">Ikome Iris Efeti</name>
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<series><title level="j">Acta crystallographica. Section E, Crystallographic communications</title>
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<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>
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<DateRevised><Year>2020</Year>
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<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>
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<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>
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<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>
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<AffiliationInfo><Affiliation>Department of Chemistry, University of Buea, PO Box 63 Buea, Cameroon.</Affiliation>
</AffiliationInfo>
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<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>
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<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>
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<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>
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<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>
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<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>
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<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>
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