NickelMaghrebV1, Pmc, Curation, bibRecord, 000006

Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol

Identifieur interne : 000006 ( Pmc/Curation ); précédent : 000005; suivant : 000007

Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol

Auteurs : Souheyla Chetioui [Algérie] ; Djamil-Azzeddine Rouag [Algérie] ; Jean-Pierre Djukic [France] ; Christian G. Bochet [Suisse] ; Rachid Touzani [Maroc] ; Corinne Bailly [France] ; Aurélien Crochet [Suisse] ; Katharina M. Fromm [Suisse]

Source :

Acta Crystallographica Section E: Crystallographic Communications [ 2056-9890 ] ; 2016.

RBID : PMC:4971848

Abstract

In the title copper(II) complex, the metal atom is coordinated by two N atoms and two O atoms from two bidentate (E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol ligands, forming a slightly distorted square-planar environment. In the isotypic nickel(II) and palladium(II) complexes, the metal atoms are located on centres of inversion, hence the metal coordination spheres have perfect square-planar geometries.

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4971848

DOI: 10.1107/S205698901601080X
PubMed: 27536389
PubMed Central: 4971848

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Le document en format XML

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)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol</title>
<author><name sortKey="Chetioui, Souheyla" sort="Chetioui, Souheyla" uniqKey="Chetioui S" first="Souheyla" last="Chetioui">Souheyla Chetioui</name>
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<author><name sortKey="Rouag, Djamil Azzeddine" sort="Rouag, Djamil Azzeddine" uniqKey="Rouag D" first="Djamil-Azzeddine" last="Rouag">Djamil-Azzeddine Rouag</name>
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<author><name sortKey="Djukic, Jean Pierre" sort="Djukic, Jean Pierre" uniqKey="Djukic J" first="Jean-Pierre" last="Djukic">Jean-Pierre Djukic</name>
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<author><name sortKey="Bochet, Christian G" sort="Bochet, Christian G" uniqKey="Bochet C" first="Christian G." last="Bochet">Christian G. Bochet</name>
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<author><name sortKey="Touzani, Rachid" sort="Touzani, Rachid" uniqKey="Touzani R" first="Rachid" last="Touzani">Rachid Touzani</name>
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<country xml:lang="fr">Maroc</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
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<author><name sortKey="Bailly, Corinne" sort="Bailly, Corinne" uniqKey="Bailly C" first="Corinne" last="Bailly">Corinne Bailly</name>
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<country xml:lang="fr">France</country>
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<author><name sortKey="Crochet, Aurelien" sort="Crochet, Aurelien" uniqKey="Crochet A" first="Aurélien" last="Crochet">Aurélien Crochet</name>
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</nlm:aff>
<country xml:lang="fr">Suisse</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
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<author><name sortKey="Fromm, Katharina M" sort="Fromm, Katharina M" uniqKey="Fromm K" first="Katharina M." last="Fromm">Katharina M. Fromm</name>
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<country xml:lang="fr">Suisse</country>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (<italic>E</italic>
)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol</title>
<author><name sortKey="Chetioui, Souheyla" sort="Chetioui, Souheyla" uniqKey="Chetioui S" first="Souheyla" last="Chetioui">Souheyla Chetioui</name>
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</nlm:aff>
<country xml:lang="fr">Algérie</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
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<author><name sortKey="Rouag, Djamil Azzeddine" sort="Rouag, Djamil Azzeddine" uniqKey="Rouag D" first="Djamil-Azzeddine" last="Rouag">Djamil-Azzeddine Rouag</name>
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</nlm:aff>
<country xml:lang="fr">Algérie</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Djukic, Jean Pierre" sort="Djukic, Jean Pierre" uniqKey="Djukic J" first="Jean-Pierre" last="Djukic">Jean-Pierre Djukic</name>
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</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
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<author><name sortKey="Bochet, Christian G" sort="Bochet, Christian G" uniqKey="Bochet C" first="Christian G." last="Bochet">Christian G. Bochet</name>
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</nlm:aff>
<country xml:lang="fr">Suisse</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Touzani, Rachid" sort="Touzani, Rachid" uniqKey="Touzani R" first="Rachid" last="Touzani">Rachid Touzani</name>
<affiliation wicri:level="1"><nlm:aff id="d">Laboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000 Oujda,<country>Morocco</country>
</nlm:aff>
<country xml:lang="fr">Maroc</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
<affiliation wicri:level="1"><nlm:aff id="e">Faculté Pluridisciplinaire Nador BP 300, Selouane 62702, Nador,<country>Morocco</country>
</nlm:aff>
<country xml:lang="fr">Maroc</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Bailly, Corinne" sort="Bailly, Corinne" uniqKey="Bailly C" first="Corinne" last="Bailly">Corinne Bailly</name>
<affiliation wicri:level="1"><nlm:aff id="f">Service de Radiocristallographie, Institut de Chimie, Université de Strasbourg, UMR 7177, 67008 Strasbourg Cedex,<country>France</country>
</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Crochet, Aurelien" sort="Crochet, Aurelien" uniqKey="Crochet A" first="Aurélien" last="Crochet">Aurélien Crochet</name>
<affiliation wicri:level="1"><nlm:aff id="g">Fribourg Center for Nanomaterials, FriMat, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg,<country>Switzerland</country>
</nlm:aff>
<country xml:lang="fr">Suisse</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</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 wicri:level="1"><nlm:aff id="c">Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg,<country>Switzerland</country>
</nlm:aff>
<country xml:lang="fr">Suisse</country>
<wicri:regionArea># see nlm:aff country strict</wicri:regionArea>
</affiliation>
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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"><p>In the title copper(II) complex, the metal atom is coordinated by two N atoms and two O atoms from two bidentate (<italic>E</italic>
)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol ligands, forming a slightly distorted square-planar environment. In the isotypic nickel(II) and palladium(II) complexes, the metal atoms are located on centres of inversion, hence the metal coordination spheres have perfect square-planar geometries.</p>
</div>
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<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">27536389</article-id>
<article-id pub-id-type="pmc">4971848</article-id>
<article-id pub-id-type="publisher-id">su5299</article-id>
<article-id pub-id-type="doi">10.1107/S205698901601080X</article-id>
<article-id pub-id-type="coden">ACSECI</article-id>
<article-id pub-id-type="pii">S205698901601080X</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Research Communications</subject>
</subj-group>
</article-categories>
<title-group><article-title>Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (<italic>E</italic>
)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol</article-title>
<alt-title><italic>[Cu(C<sub>16</sub>
H<sub>8</sub>
Br<sub>3</sub>
N<sub>2</sub>
O)<sub>2</sub>
], [Ni(C<sub>16</sub>
H<sub>8</sub>
Br<sub>3</sub>
N<sub>2</sub>
O)<sub>2</sub>
] and [Pd(C<sub>16</sub>
H<sub>8</sub>
Br<sub>3</sub>
N<sub>2</sub>
O)<sub>2</sub>
]</italic>
</alt-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Chetioui</surname>
<given-names>Souheyla</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
<xref ref-type="corresp" rid="cor">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Rouag</surname>
<given-names>Djamil-Azzeddine</given-names>
</name>
<xref ref-type="aff" rid="a">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Djukic</surname>
<given-names>Jean-Pierre</given-names>
</name>
<xref ref-type="aff" rid="b">b</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Bochet</surname>
<given-names>Christian G.</given-names>
</name>
<xref ref-type="aff" rid="c">c</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Touzani</surname>
<given-names>Rachid</given-names>
</name>
<xref ref-type="aff" rid="d">d</xref>
<xref ref-type="aff" rid="e">e</xref>
<xref ref-type="corresp" rid="cor">*</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Bailly</surname>
<given-names>Corinne</given-names>
</name>
<xref ref-type="aff" rid="f">f</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Crochet</surname>
<given-names>Aurélien</given-names>
</name>
<xref ref-type="aff" rid="g">g</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Fromm</surname>
<given-names>Katharina M.</given-names>
</name>
<xref ref-type="aff" rid="c">c</xref>
</contrib>
<aff id="a"><label>a</label>
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,<country>Algeria</country>
</aff>
<aff id="b"><label>b</label>
Laboratoire de Chimie et Systémique Organométallique (LCSOM), Institut de Chimie, Université de Strasbourg, UMR 7177., 4 rue Blaise Pascal, F-67070 Strasbourg Cedex,<country>France</country>
</aff>
<aff id="c"><label>c</label>
Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg,<country>Switzerland</country>
</aff>
<aff id="d"><label>d</label>
Laboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000 Oujda,<country>Morocco</country>
</aff>
<aff id="e"><label>e</label>
Faculté Pluridisciplinaire Nador BP 300, Selouane 62702, Nador,<country>Morocco</country>
</aff>
<aff id="f"><label>f</label>
Service de Radiocristallographie, Institut de Chimie, Université de Strasbourg, UMR 7177, 67008 Strasbourg Cedex,<country>France</country>
</aff>
<aff id="g"><label>g</label>
Fribourg Center for Nanomaterials, FriMat, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg,<country>Switzerland</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor">Correspondence e-mail: <email>souheilachetioui@yahoo.fr</email>
, <email>touzanir@yahoo.fr</email>
</corresp>
</author-notes>
<pub-date pub-type="collection"><day>01</day>
<month>8</month>
<year>2016</year>
</pub-date>
<pub-date pub-type="epub"><day>12</day>
<month>7</month>
<year>2016</year>
</pub-date>
<pub-date pub-type="pmc-release"><day>12</day>
<month>7</month>
<year>2016</year>
</pub-date>
<pmc-comment> PMC Release delay is 0 months and 0 days and was based on the . </pmc-comment>
      <volume>72</volume>
<issue>Pt 8</issue>
<issue-id pub-id-type="publisher-id">e160800</issue-id>
<fpage>1093</fpage>
<lpage>1098</lpage>
<history><date date-type="received"><day>07</day>
<month>5</month>
<year>2016</year>
</date>
<date date-type="accepted"><day>04</day>
<month>7</month>
<year>2016</year>
</date>
</history>
<permissions><copyright-statement>© Chetioui et al. 2016</copyright-statement>
<copyright-year>2016</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
Licence, which permits unrestricted use,
distribution, and reproduction in any medium,
provided the original authors and source are
cited.</license-p>
</license>
</permissions>
<self-uri xlink:type="simple" xlink:href="http://dx.doi.org/10.1107/S205698901601080X">A full version of this
article is available from Crystallography Journals Online.</self-uri>
<abstract abstract-type="toc"><p>In the title copper(II) complex, the metal atom is coordinated by two N atoms and two O atoms from two bidentate (<italic>E</italic>
)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol ligands, forming a slightly distorted square-planar environment. In the isotypic nickel(II) and palladium(II) complexes, the metal atoms are located on centres of inversion, hence the metal coordination spheres have perfect square-planar geometries.</p>
</abstract>
<abstract><p>In the copper(II) complex, bis{(<italic>E</italic>
)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-olato}copper(II), [Cu(C<sub>16</sub>
H<sub>8</sub>
Br<sub>3</sub>
N<sub>2</sub>
O)<sub>2</sub>
], (I), the metal cation is coordinated by two N atoms and two O atoms from two bidentate (<italic>E</italic>
)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-olate ligands, forming a slightly distorted square-planar environment. In one of the ligands, the tribromobenzene ring is inclined to the naphthalene ring system by 37.4 (5)°, creating a weak intramolecular Cu⋯Br interaction [3.134 (2) Å], while in the other ligand, the tribromobenzene ring is inclined to the naphthalene ring system by 72.1 (6)°. In the isotypic nickel(II) and palladium(II) complexes, namely bis{(<italic>E</italic>
)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-olato}nickel(II), [Ni(C<sub>16</sub>
H<sub>8</sub>
Br<sub>3</sub>
N<sub>2</sub>
O)<sub>2</sub>
], (II), and bis{(<italic>E</italic>
)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-olato}palladium(II), [Pd(C<sub>16</sub>
H<sub>8</sub>
Br<sub>3</sub>
N<sub>2</sub>
O)<sub>2</sub>
], (III), respectively, the metal atoms are located on centres of inversion, hence the metal coordination spheres have perfect square-planar geometries. The tribromobenzene 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), molecules are linked by C—H⋯Br hydrogen bonds, forming chains along [010]. The chains are linked by C—H⋯π interactions, forming sheets parallel to (011). In the crystals of (II) and (III), molecules are linked by C—H⋯π interactions, 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 <italic>PLATON</italic>
 [Spek (2015<xref ref-type="bibr" rid="bb23"> ▸</xref>
). <italic>Acta Cryst.</italic>
 C<bold>71</bold>
, 9–18]. The formula mass and unit-cell characteristics of the disordered solvent molecules were not taken into account during refinement.</p>
</abstract>
<kwd-group><kwd>crystal structures</kwd>
<kwd>copper(II)</kwd>
<kwd>nickel(II)</kwd>
<kwd>palladium(II)</kwd>
<kwd>isotypic complexes</kwd>
<kwd>Cu⋯Br short contact</kwd>
<kwd>C—H⋯Br hydrogen bonds</kwd>
<kwd>C—H⋯π interactions</kwd>
</kwd-group>
</article-meta>
</front>
<floats-group><fig id="fig1" position="float"><label>Figure 1</label>
<caption><p>The molecular structure of compound (I)<xref ref-type="chem" rid="scheme1"></xref>
, with atom labelling and 50% probability displacement ellipsoids. The intramolecular Cu⋯Br contact is shown as a dashed line (details are given in Table 1<xref ref-type="table" rid="table1"> ▸</xref>
).</p>
</caption>
<graphic xlink:href="e-72-01093-fig1"></graphic>
</fig>
<fig id="fig2" position="float"><label>Figure 2</label>
<caption><p>The molecular structure of compound (II)<xref ref-type="chem" rid="scheme1"></xref>
, with atom labelling and 50% probability displacement ellipsoids. The unlabelled atoms are related to the labelled atoms by the symmetry operation (−<italic>x</italic>
 + 1, −<italic>y</italic>
 + 1, −<italic>z</italic>
 + 1).</p>
</caption>
<graphic xlink:href="e-72-01093-fig2"></graphic>
</fig>
<fig id="fig3" position="float"><label>Figure 3</label>
<caption><p>The molecular structure of compound (III)<xref ref-type="chem" rid="scheme1"></xref>
, with atom labelling and 50% probability displacement ellipsoids. The unlabelled atoms are related to the labelled atoms by the symmetry operation (−<italic>x</italic>
, −<italic>y</italic>
, −<italic>z</italic>
).</p>
</caption>
<graphic xlink:href="e-72-01093-fig3"></graphic>
</fig>
<fig id="fig4" position="float"><label>Figure 4</label>
<caption><p>The crystal packing of compound (I)<xref ref-type="chem" rid="scheme1"></xref>
, viewed along the <italic>a</italic>
 axis. The intermolecular interactions are shown as dashed lines (see Table 4<xref ref-type="table" rid="table4"> ▸</xref>
 for details), and for clarity only the H atoms involved in these interactions have been included.</p>
</caption>
<graphic xlink:href="e-72-01093-fig4"></graphic>
</fig>
<fig id="fig5" position="float"><label>Figure 5</label>
<caption><p>The crystal packing of compound (II)<xref ref-type="chem" rid="scheme1"></xref>
, viewed along the normal to (10<inline-formula><inline-graphic xlink:href="e-72-01093-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
). The intermolecular interactions are shown as dashed lines (see Table 5<xref ref-type="table" rid="table5"> ▸</xref>
 for details), and for clarity only the H atoms involved in these interactions have been included.</p>
</caption>
<graphic xlink:href="e-72-01093-fig5"></graphic>
</fig>
<fig id="fig6" position="float"><label>Figure 6</label>
<caption><p>The results of the database search (CSD; Groom <italic>et al.</italic>
, 2016<xref ref-type="bibr" rid="bb12"> ▸</xref>
) for four-coordinate metal complexes of the ligand (<italic>E</italic>
)-1-(phenyldiazenyl)naphthalen-2-ol and its derivatives.</p>
</caption>
<graphic xlink:href="e-72-01093-fig6"></graphic>
</fig>
<table-wrap id="table1" position="float"><label>Table 1</label>
<caption><title>Selected geometric parameters (Å, °) for (I)<xref ref-type="chem" rid="scheme1"></xref>
</title>
</caption>
<table frame="hsides" rules="groups"><tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">Cu1—Br4</td>
<td rowspan="1" colspan="1" align="char" valign="top">3.134 (2)</td>
<td rowspan="1" colspan="1" align="left" valign="top">Cu1—O1</td>
<td rowspan="1" colspan="1" align="char" valign="top">1.892 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Cu1—N1</td>
<td rowspan="1" colspan="1" align="char" valign="top">1.947 (12)</td>
<td rowspan="1" colspan="1" align="left" valign="top">Cu1—O2</td>
<td rowspan="1" colspan="1" align="char" valign="top">1.888 (8)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Cu1—N3</td>
<td rowspan="1" colspan="1" align="char" valign="top">1.970 (11)</td>
<td rowspan="1" colspan="1" align="left" valign="top"> </td>
<td rowspan="1" colspan="1" align="char" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"> </td>
<td rowspan="1" colspan="1" align="char" valign="top"> </td>
<td rowspan="1" colspan="1" align="left" valign="top"> </td>
<td rowspan="1" colspan="1" align="char" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">O2—Cu1—O1</td>
<td rowspan="1" colspan="1" align="char" valign="top">169.4 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">O2—Cu1—N3</td>
<td rowspan="1" colspan="1" align="char" valign="top">87.6 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">O2—Cu1—N1</td>
<td rowspan="1" colspan="1" align="char" valign="top">91.3 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">O1—Cu1—N3</td>
<td rowspan="1" colspan="1" align="char" valign="top">92.1 (4)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">O1—Cu1—N1</td>
<td rowspan="1" colspan="1" align="char" valign="top">90.9 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">N1—Cu1—N3</td>
<td rowspan="1" colspan="1" align="char" valign="top">169.3 (5)</td>
</tr>
</tbody>
</table>
</table-wrap>
<table-wrap id="table2" position="float"><label>Table 2</label>
<caption><title>Selected geometric parameters (Å, °) for (II)<xref ref-type="chem" rid="scheme1"></xref>
</title>
</caption>
<table frame="hsides" rules="groups"><tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">Ni—N1</td>
<td rowspan="1" colspan="1" align="char" valign="top">1.876 (3)</td>
<td rowspan="1" colspan="1" align="left" valign="top">Ni—O1</td>
<td rowspan="1" colspan="1" align="char" valign="top">1.821 (3)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"> </td>
<td rowspan="1" colspan="1" align="char" valign="top"> </td>
<td rowspan="1" colspan="1" align="left" valign="top"> </td>
<td rowspan="1" colspan="1" align="char" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">O1—Ni—O1<sup>i</sup>
</td>
<td rowspan="1" colspan="1" align="char" valign="top">180</td>
<td rowspan="1" colspan="1" align="left" valign="top">O1<sup>i</sup>
—Ni—N1</td>
<td rowspan="1" colspan="1" align="char" valign="top">87.41 (14)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">O1—Ni—N1</td>
<td rowspan="1" colspan="1" align="char" valign="top">92.59 (14)</td>
<td rowspan="1" colspan="1" align="left" valign="top">N1—Ni—N1<sup>i</sup>
</td>
<td rowspan="1" colspan="1" align="char" valign="top">180</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry code: (i) <inline-formula><inline-graphic xlink:href="e-72-01093-efi2.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table3" position="float"><label>Table 3</label>
<caption><title>Selected geometric parameters (Å, °) for (III)<xref ref-type="chem" rid="scheme1"></xref>
</title>
</caption>
<table frame="hsides" rules="groups"><tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">Pd1—N1</td>
<td rowspan="1" colspan="1" align="char" valign="top">2.004 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">Pd1—O1</td>
<td rowspan="1" colspan="1" align="char" valign="top">1.972 (5)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top"> </td>
<td rowspan="1" colspan="1" align="char" valign="top"> </td>
<td rowspan="1" colspan="1" align="left" valign="top"> </td>
<td rowspan="1" colspan="1" align="char" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">O1—Pd1—O1<sup>i</sup>
</td>
<td rowspan="1" colspan="1" align="char" valign="top">180</td>
<td rowspan="1" colspan="1" align="left" valign="top">O1<sup>i</sup>
—Pd1—N1</td>
<td rowspan="1" colspan="1" align="char" valign="top">88.7 (2)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">O1—Pd1—N1</td>
<td rowspan="1" colspan="1" align="char" valign="top">91.3 (2)</td>
<td rowspan="1" colspan="1" align="left" valign="top">N1—Pd1—N1<sup>i</sup>
</td>
<td rowspan="1" colspan="1" align="char" valign="top">180</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry code: (i) <inline-formula><inline-graphic xlink:href="e-72-01093-efi3.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table4" position="float"><label>Table 4</label>
<caption><title>Hydrogen-bond geometry (Å, °) for (I)<xref ref-type="chem" rid="scheme1"></xref>
</title>
<p><italic>Cg</italic>
1 is the centroid of the C27–C32 ring.</p>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">C5—H5⋯Br6<sup>i</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.95</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.75</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.546 (15)</td>
<td rowspan="1" colspan="1" align="left" valign="top">142</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">C3—H3⋯<italic>Cg</italic>
1<sup>ii</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.95</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.99</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.729 (15)</td>
<td rowspan="1" colspan="1" align="left" valign="top">136</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry codes: (i) <inline-formula><inline-graphic xlink:href="e-72-01093-efi4.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
; (ii) <inline-formula><inline-graphic xlink:href="e-72-01093-efi5.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table5" position="float"><label>Table 5</label>
<caption><title>Hydrogen-bond geometry (Å, °) for (II)<xref ref-type="chem" rid="scheme1"></xref>
</title>
<p><italic>Cg</italic>
2 is the centroid of the C1–C6 ring.</p>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">C10—H10⋯<italic>Cg</italic>
2<sup>ii</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.95</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.71</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.391 (5)</td>
<td rowspan="1" colspan="1" align="left" valign="top">130</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry code: (ii) <inline-formula><inline-graphic xlink:href="e-72-01093-efi6.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table6" position="float"><label>Table 6</label>
<caption><title>Hydrogen-bond geometry (Å, °) for (III)<xref ref-type="chem" rid="scheme1"></xref>
</title>
<p><italic>Cg</italic>
2 is the centroid of the C1–C6 ring.</p>
</caption>
<table frame="hsides" rules="groups"><thead valign="bottom"><tr><th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom">H⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
⋯<italic>A</italic>
</th>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="bottom"><italic>D</italic>
—H⋯<italic>A</italic>
</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="1" align="left" valign="top">C10—H10⋯<italic>Cg</italic>
2<sup>ii</sup>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.93</td>
<td rowspan="1" colspan="1" align="left" valign="top">2.70</td>
<td rowspan="1" colspan="1" align="left" valign="top">3.371 (8)</td>
<td rowspan="1" colspan="1" align="left" valign="top">129</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Symmetry code: (ii) <inline-formula><inline-graphic xlink:href="e-72-01093-efi7.jpg" mimetype="image" mime-subtype="gif"></inline-graphic>
</inline-formula>
.</p>
</table-wrap-foot>
</table-wrap>
<table-wrap id="table7" position="float"><label>Table 7</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>
<th style="border-bottom:1px solid black;" rowspan="1" colspan="1" align="left" valign="top">(III)</th>
</tr>
</thead>
<tbody valign="top"><tr><td rowspan="1" colspan="4" 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">[Cu(C<sub>16</sub>
H<sub>8</sub>
Br<sub>3</sub>
N<sub>2</sub>
O)<sub>2</sub>
]</td>
<td rowspan="1" colspan="1" align="left" valign="top">[Ni(C<sub>16</sub>
H<sub>8</sub>
Br<sub>3</sub>
N<sub>2</sub>
O)<sub>2</sub>
]</td>
<td rowspan="1" colspan="1" align="left" valign="top">[Pd(C<sub>16</sub>
H<sub>8</sub>
Br<sub>3</sub>
N<sub>2</sub>
O)<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">1031.49</td>
<td rowspan="1" colspan="1" align="left" valign="top">1026.66</td>
<td rowspan="1" colspan="1" align="left" valign="top">1074.35</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">Monoclinic, <italic>P</italic>
2<sub>1</sub>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">Monoclinic, <italic>P</italic>
2<sub>1</sub>
/<italic>n</italic>
</td>
<td rowspan="1" colspan="1" align="left" valign="top">Monoclinic, <italic>P</italic>
2<sub>1</sub>
/<italic>n</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">173</td>
<td rowspan="1" colspan="1" align="left" valign="top">173</td>
<td rowspan="1" colspan="1" align="left" valign="top">200</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">11.9423 (7), 12.1314 (10), 12.8974 (10)</td>
<td rowspan="1" colspan="1" align="left" valign="top">11.0909 (6), 12.4571 (6), 12.5382 (7)</td>
<td rowspan="1" colspan="1" align="left" valign="top">11.1896 (8), 12.4540 (8), 12.5511 (9)</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">β (°)</td>
<td rowspan="1" colspan="1" align="left" valign="top">107.032 (4)</td>
<td rowspan="1" colspan="1" align="left" valign="top">107.820 (2)</td>
<td rowspan="1" colspan="1" align="left" valign="top">107.749 (5)</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">1786.6 (2)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1649.17 (15)</td>
<td rowspan="1" colspan="1" align="left" valign="top">1665.8 (2)</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">2</td>
<td rowspan="1" colspan="1" align="left" valign="top">2</td>
<td rowspan="1" colspan="1" align="left" valign="top">2</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>
<td rowspan="1" colspan="1" align="left" valign="top">Cu <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">7.36</td>
<td rowspan="1" colspan="1" align="left" valign="top">7.89</td>
<td rowspan="1" colspan="1" align="left" valign="top">13.23</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">0.20 × 0.15 × 0.06</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.30 × 0.22 × 0.06</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.12 × 0.09 × 0.03</td>
</tr>
<tr><td rowspan="1" colspan="4" align="left" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="4" 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">Nonius KappaCCD</td>
<td rowspan="1" colspan="1" align="left" valign="top">Nonius KappaCCD</td>
<td rowspan="1" colspan="1" align="left" valign="top">STOE <italic>IPDS</italic>
 2T</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>MULABS</italic>
; Spek, 2009)</td>
<td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>MULABS</italic>
; Spek, 2009)</td>
<td rowspan="1" colspan="1" align="left" valign="top">Multi-scan (<italic>MULABS</italic>
; Spek, 2009)</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">0.311, 0.386</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.151, 0.317</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.360, 1.000</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">14985, 7819, 4785</td>
<td rowspan="1" colspan="1" align="left" valign="top">11360, 3745, 2214</td>
<td rowspan="1" colspan="1" align="left" valign="top">13003, 2895, 2371</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">0.077</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.094</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.142</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">0.650</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.649</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.600</td>
</tr>
<tr><td rowspan="1" colspan="4" align="left" valign="top"> </td>
</tr>
<tr><td rowspan="1" colspan="4" 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">0.064, 0.140, 0.96</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.043, 0.096, 0.95</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.057, 0.170, 1.11</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">7819</td>
<td rowspan="1" colspan="1" align="left" valign="top">3745</td>
<td rowspan="1" colspan="1" align="left" valign="top">2895</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">388</td>
<td rowspan="1" colspan="1" align="left" valign="top">205</td>
<td rowspan="1" colspan="1" align="left" valign="top">206</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">No. of restraints</td>
<td rowspan="1" colspan="1" align="left" valign="top">2</td>
<td rowspan="1" colspan="1" align="left" valign="top">0</td>
<td rowspan="1" colspan="1" align="left" valign="top">0</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>
<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">0.59, −0.58</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.57, −0.66</td>
<td rowspan="1" colspan="1" align="left" valign="top">0.88, −1.10</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Absolute structure</td>
<td rowspan="1" colspan="1" align="left" valign="top">Flack <italic>x</italic>
 determined using 1648 quotients [(<italic>I</italic>
<sup>+</sup>
)-(<italic>I</italic>
<sup>-</sup>
)]/[(<italic>I</italic>
<sup>+</sup>
)+(<italic>I</italic>
<sup>-</sup>
)] (Parsons <italic>et al.</italic>
, 2013<xref ref-type="bibr" rid="bb18"> ▸</xref>
)</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
</tr>
<tr><td rowspan="1" colspan="1" align="left" valign="top">Absolute structure parameter</td>
<td rowspan="1" colspan="1" align="left" valign="top">−0.006 (14)</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
<td rowspan="1" colspan="1" align="left" valign="top">–</td>
</tr>
</tbody>
</table>
<table-wrap-foot><p>Computer programs: <italic>COLLECT</italic>
 (Nonius, 1998<xref ref-type="bibr" rid="bb16"> ▸</xref>
), <italic>X-AREA</italic>
 and <italic>X-RED32</italic>
 (Stoe & Cie, 2002<xref ref-type="bibr" rid="bb24"> ▸</xref>
), <italic>DENZO</italic>
 (Otwinowski & Minor, 1997<xref ref-type="bibr" rid="bb17"> ▸</xref>
), <italic>SIR97</italic>
 (Altomare <italic>et al.</italic>
, 1999<xref ref-type="bibr" rid="bb2"> ▸</xref>
), <italic>SHELXS2014</italic>
 (Sheldrick, 2008<xref ref-type="bibr" rid="bb20"> ▸</xref>
), <italic>SHELXL2014</italic>
 (Sheldrick, 2015<xref ref-type="bibr" rid="bb21"> ▸</xref>
), <italic>Mercury</italic>
 (Macrae <italic>et al.</italic>
, 2008<xref ref-type="bibr" rid="bb15"> ▸</xref>
) and <italic>PLATON</italic>
 (Spek, 2009<xref ref-type="bibr" rid="bb22"> ▸</xref>
).</p>
</table-wrap-foot>
</table-wrap>
</floats-group>
</pmc>
</record>

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Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tri­bromo­phen­yl)diazen­yl]naphthalen-2-ol

Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tri­bromo­phen­yl)diazen­yl]naphthalen-2-ol

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Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol

Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol