Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol.
Identifieur interne : 000012 ( PubMed/Corpus ); précédent : 000011; suivant : 000013Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol.
Auteurs : Souheyla Chetioui ; Djamil-Azzeddine Rouag ; Jean-Pierre Djukic ; Christian G. Bochet ; Rachid Touzani ; Corinne Bailly ; Aurélien Crochet ; Katharina M. FrommSource :
- Acta crystallographica. Section E, Crystallographic communications ; 2016.
Abstract
In the copper(II) complex, bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naph-thalen-2-olato}copper(II), [Cu(C16H8Br3N2O)2], (I), the metal cation is coord-inated by two N atoms and two O atoms from two bidentate (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olate ligands, forming a slightly distorted square-planar environment. In one of the ligands, the tri-bromo-benzene ring is inclined to the naphthalene ring system by 37.4 (5)°, creating a weak intra-molecular Cu⋯Br inter-action [3.134 (2) Å], while in the other ligand, the tri-bromo-benzene ring is inclined to the naphthalene ring system by 72.1 (6)°. In the isotypic nickel(II) and palladium(II) complexes, namely bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olato}nickel(II), [Ni(C16H8Br3N2O)2], (II), and bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olato}palladium(II), [Pd(C16H8Br3N2O)2], (III), respectively, the metal atoms are located on centres of inversion, hence the metal coordination spheres have perfect square-planar geometries. The tri-bromo-benzene rings are inclined to the naphthalene ring systems by 80.79 (18)° in (II) and by 80.8 (3)° in (III). In the crystal of (I), mol-ecules are linked by C-H⋯Br hydrogen bonds, forming chains along [010]. The chains are linked by C-H⋯π inter-actions, forming sheets parallel to (011). In the crystals of (II) and (III), mol-ecules are linked by C-H⋯π inter-actions, forming slabs parallel to (10-1). For the copper(II) complex (I), a region of disordered electron density was corrected for using the SQUEEZE routine in PLATON [Spek (2015 ▸). Acta Cryst. C71, 9-18]. The formula mass and unit-cell characteristics of the disordered solvent mol-ecules were not taken into account during refinement.
DOI: 10.1107/S205698901601080X
PubMed: 27536389
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol.</title><author><name sortKey="Chetioui, Souheyla" sort="Chetioui, Souheyla" uniqKey="Chetioui S" first="Souheyla" last="Chetioui">Souheyla Chetioui</name><affiliation><nlm:affiliation>Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université des Frères Mentouri Constantine, Constantine 25000, Algeria.</nlm:affiliation></affiliation></author><author><name sortKey="Rouag, Djamil Azzeddine" sort="Rouag, Djamil Azzeddine" uniqKey="Rouag D" first="Djamil-Azzeddine" last="Rouag">Djamil-Azzeddine Rouag</name><affiliation><nlm:affiliation>Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université des Frères Mentouri Constantine, Constantine 25000, Algeria.</nlm:affiliation></affiliation></author><author><name sortKey="Djukic, Jean Pierre" sort="Djukic, Jean Pierre" uniqKey="Djukic J" first="Jean-Pierre" last="Djukic">Jean-Pierre Djukic</name><affiliation><nlm:affiliation>Laboratoire de Chimie et Systémique Organométallique (LCSOM), Institut de Chimie, Université de Strasbourg, UMR 7177., 4 rue Blaise Pascal, F-67070 Strasbourg Cedex, France.</nlm:affiliation></affiliation></author><author><name sortKey="Bochet, Christian G" sort="Bochet, Christian G" uniqKey="Bochet C" first="Christian G" last="Bochet">Christian G. Bochet</name><affiliation><nlm:affiliation>Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland.</nlm:affiliation></affiliation></author><author><name sortKey="Touzani, Rachid" sort="Touzani, Rachid" uniqKey="Touzani R" first="Rachid" last="Touzani">Rachid Touzani</name><affiliation><nlm:affiliation>Laboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000 Oujda, Morocco; Faculté Pluridisciplinaire Nador BP 300, Selouane 62702, Nador, Morocco.</nlm:affiliation></affiliation></author><author><name sortKey="Bailly, Corinne" sort="Bailly, Corinne" uniqKey="Bailly C" first="Corinne" last="Bailly">Corinne Bailly</name><affiliation><nlm:affiliation>Service de Radiocristallographie, Institut de Chimie, Université de Strasbourg, UMR 7177, 67008 Strasbourg Cedex, France.</nlm:affiliation></affiliation></author><author><name sortKey="Crochet, Aurelien" sort="Crochet, Aurelien" uniqKey="Crochet A" first="Aurélien" last="Crochet">Aurélien Crochet</name><affiliation><nlm:affiliation>Fribourg Center for Nanomaterials, FriMat, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland.</nlm:affiliation></affiliation></author><author><name sortKey="Fromm, Katharina M" sort="Fromm, Katharina M" uniqKey="Fromm K" first="Katharina M" last="Fromm">Katharina M. Fromm</name><affiliation><nlm:affiliation>Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland.</nlm:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2016">2016</date><idno type="RBID">pubmed:27536389</idno><idno type="pmid">27536389</idno><idno type="doi">10.1107/S205698901601080X</idno><idno type="wicri:Area/PubMed/Corpus">000012</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000012</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol.</title><author><name sortKey="Chetioui, Souheyla" sort="Chetioui, Souheyla" uniqKey="Chetioui S" first="Souheyla" last="Chetioui">Souheyla Chetioui</name><affiliation><nlm:affiliation>Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université des Frères Mentouri Constantine, Constantine 25000, Algeria.</nlm:affiliation></affiliation></author><author><name sortKey="Rouag, Djamil Azzeddine" sort="Rouag, Djamil Azzeddine" uniqKey="Rouag D" first="Djamil-Azzeddine" last="Rouag">Djamil-Azzeddine Rouag</name><affiliation><nlm:affiliation>Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université des Frères Mentouri Constantine, Constantine 25000, Algeria.</nlm:affiliation></affiliation></author><author><name sortKey="Djukic, Jean Pierre" sort="Djukic, Jean Pierre" uniqKey="Djukic J" first="Jean-Pierre" last="Djukic">Jean-Pierre Djukic</name><affiliation><nlm:affiliation>Laboratoire de Chimie et Systémique Organométallique (LCSOM), Institut de Chimie, Université de Strasbourg, UMR 7177., 4 rue Blaise Pascal, F-67070 Strasbourg Cedex, France.</nlm:affiliation></affiliation></author><author><name sortKey="Bochet, Christian G" sort="Bochet, Christian G" uniqKey="Bochet C" first="Christian G" last="Bochet">Christian G. Bochet</name><affiliation><nlm:affiliation>Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland.</nlm:affiliation></affiliation></author><author><name sortKey="Touzani, Rachid" sort="Touzani, Rachid" uniqKey="Touzani R" first="Rachid" last="Touzani">Rachid Touzani</name><affiliation><nlm:affiliation>Laboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000 Oujda, Morocco; Faculté Pluridisciplinaire Nador BP 300, Selouane 62702, Nador, Morocco.</nlm:affiliation></affiliation></author><author><name sortKey="Bailly, Corinne" sort="Bailly, Corinne" uniqKey="Bailly C" first="Corinne" last="Bailly">Corinne Bailly</name><affiliation><nlm:affiliation>Service de Radiocristallographie, Institut de Chimie, Université de Strasbourg, UMR 7177, 67008 Strasbourg Cedex, France.</nlm:affiliation></affiliation></author><author><name sortKey="Crochet, Aurelien" sort="Crochet, Aurelien" uniqKey="Crochet A" first="Aurélien" last="Crochet">Aurélien Crochet</name><affiliation><nlm:affiliation>Fribourg Center for Nanomaterials, FriMat, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland.</nlm:affiliation></affiliation></author><author><name sortKey="Fromm, Katharina M" sort="Fromm, Katharina M" uniqKey="Fromm K" first="Katharina M" last="Fromm">Katharina M. Fromm</name><affiliation><nlm:affiliation>Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland.</nlm:affiliation></affiliation></author></analytic><series><title level="j">Acta crystallographica. Section E, Crystallographic communications</title><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">In the copper(II) complex, bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naph-thalen-2-olato}copper(II), [Cu(C16H8Br3N2O)2], (I), the metal cation is coord-inated by two N atoms and two O atoms from two bidentate (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olate ligands, forming a slightly distorted square-planar environment. In one of the ligands, the tri-bromo-benzene ring is inclined to the naphthalene ring system by 37.4 (5)°, creating a weak intra-molecular Cu⋯Br inter-action [3.134 (2) Å], while in the other ligand, the tri-bromo-benzene ring is inclined to the naphthalene ring system by 72.1 (6)°. In the isotypic nickel(II) and palladium(II) complexes, namely bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olato}nickel(II), [Ni(C16H8Br3N2O)2], (II), and bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olato}palladium(II), [Pd(C16H8Br3N2O)2], (III), respectively, the metal atoms are located on centres of inversion, hence the metal coordination spheres have perfect square-planar geometries. The tri-bromo-benzene rings are inclined to the naphthalene ring systems by 80.79 (18)° in (II) and by 80.8 (3)° in (III). In the crystal of (I), mol-ecules are linked by C-H⋯Br hydrogen bonds, forming chains along [010]. The chains are linked by C-H⋯π inter-actions, forming sheets parallel to (011). In the crystals of (II) and (III), mol-ecules are linked by C-H⋯π inter-actions, forming slabs parallel to (10-1). For the copper(II) complex (I), a region of disordered electron density was corrected for using the SQUEEZE routine in PLATON [Spek (2015 ▸). Acta Cryst. C71, 9-18]. The formula mass and unit-cell characteristics of the disordered solvent mol-ecules were not taken into account during refinement.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">27536389</PMID><DateCreated><Year>2016</Year><Month>08</Month><Day>18</Day></DateCreated><DateCompleted><Year>2016</Year><Month>08</Month><Day>18</Day></DateCompleted><DateRevised><Year>2016</Year><Month>08</Month><Day>20</Day></DateRevised><Article PubModel="Electronic-eCollection"><Journal><JournalIssue CitedMedium="Print"><Volume>72</Volume><Issue>Pt 8</Issue><PubDate><Year>2016</Year><Month>Aug</Month><Day>01</Day></PubDate></JournalIssue><Title>Acta crystallographica. Section E, Crystallographic communications</Title><ISOAbbreviation>Acta Crystallogr E Crystallogr Commun</ISOAbbreviation></Journal><ArticleTitle>Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-ol.</ArticleTitle><Pagination><MedlinePgn>1093-8</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1107/S205698901601080X</ELocationID><Abstract><AbstractText>In the copper(II) complex, bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naph-thalen-2-olato}copper(II), [Cu(C16H8Br3N2O)2], (I), the metal cation is coord-inated by two N atoms and two O atoms from two bidentate (E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olate ligands, forming a slightly distorted square-planar environment. In one of the ligands, the tri-bromo-benzene ring is inclined to the naphthalene ring system by 37.4 (5)°, creating a weak intra-molecular Cu⋯Br inter-action [3.134 (2) Å], while in the other ligand, the tri-bromo-benzene ring is inclined to the naphthalene ring system by 72.1 (6)°. In the isotypic nickel(II) and palladium(II) complexes, namely bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olato}nickel(II), [Ni(C16H8Br3N2O)2], (II), and bis-{(E)-1-[(2,4,6-tri-bromo-phen-yl)diazen-yl]naphthalen-2-olato}palladium(II), [Pd(C16H8Br3N2O)2], (III), respectively, the metal atoms are located on centres of inversion, hence the metal coordination spheres have perfect square-planar geometries. The tri-bromo-benzene rings are inclined to the naphthalene ring systems by 80.79 (18)° in (II) and by 80.8 (3)° in (III). In the crystal of (I), mol-ecules are linked by C-H⋯Br hydrogen bonds, forming chains along [010]. The chains are linked by C-H⋯π inter-actions, forming sheets parallel to (011). In the crystals of (II) and (III), mol-ecules are linked by C-H⋯π inter-actions, forming slabs parallel to (10-1). For the copper(II) complex (I), a region of disordered electron density was corrected for using the SQUEEZE routine in PLATON [Spek (2015 ▸). Acta Cryst. C71, 9-18]. The formula mass and unit-cell characteristics of the disordered solvent mol-ecules were not taken into account during refinement.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Chetioui</LastName><ForeName>Souheyla</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université des Frères Mentouri Constantine, Constantine 25000, Algeria.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Rouag</LastName><ForeName>Djamil-Azzeddine</ForeName><Initials>DA</Initials><AffiliationInfo><Affiliation>Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université des Frères Mentouri Constantine, Constantine 25000, Algeria.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Djukic</LastName><ForeName>Jean-Pierre</ForeName><Initials>JP</Initials><AffiliationInfo><Affiliation>Laboratoire de Chimie et Systémique Organométallique (LCSOM), Institut de Chimie, Université de Strasbourg, UMR 7177., 4 rue Blaise Pascal, F-67070 Strasbourg Cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Bochet</LastName><ForeName>Christian G</ForeName><Initials>CG</Initials><AffiliationInfo><Affiliation>Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Touzani</LastName><ForeName>Rachid</ForeName><Initials>R</Initials><AffiliationInfo><Affiliation>Laboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000 Oujda, Morocco; Faculté Pluridisciplinaire Nador BP 300, Selouane 62702, Nador, Morocco.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Bailly</LastName><ForeName>Corinne</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Service de Radiocristallographie, Institut de Chimie, Université de Strasbourg, UMR 7177, 67008 Strasbourg Cedex, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Crochet</LastName><ForeName>Aurélien</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Fribourg Center for Nanomaterials, FriMat, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Fromm</LastName><ForeName>Katharina M</ForeName><Initials>KM</Initials><AffiliationInfo><Affiliation>Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg, Switzerland.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>07</Month><Day>12</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Acta Crystallogr E Crystallogr Commun</MedlineTA><NlmUniqueID>101648987</NlmUniqueID></MedlineJournalInfo><OtherID Source="NLM">PMC4971848</OtherID><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Cu⋯Br short contact</Keyword><Keyword MajorTopicYN="N">C—H⋯Br hydrogen bonds</Keyword><Keyword MajorTopicYN="N">C—H⋯π interactions</Keyword><Keyword MajorTopicYN="N">copper(II)</Keyword><Keyword MajorTopicYN="N">crystal structures</Keyword><Keyword MajorTopicYN="N">isotypic complexes</Keyword><Keyword MajorTopicYN="N">nickel(II)</Keyword><Keyword MajorTopicYN="N">palladium(II)</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2016</Year><Month>05</Month><Day>07</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2016</Year><Month>07</Month><Day>04</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>8</Month><Day>19</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>8</Month><Day>19</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2016</Year><Month>8</Month><Day>19</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate></History><PublicationStatus>epublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">27536389</ArticleId><ArticleId IdType="doi">10.1107/S205698901601080X</ArticleId><ArticleId IdType="pii">su5299</ArticleId><ArticleId IdType="pmc">PMC4971848</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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