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/Corpus ); précédent : 000005; suivant : 000007Crystal 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 ; Djamil-Azzeddine Rouag ; Jean-Pierre Djukic ; Christian G. Bochet ; Rachid Touzani ; Corinne Bailly ; Aurélien Crochet ; Katharina M. FrommSource :
- Acta Crystallographica Section E: Crystallographic Communications [ 2056-9890 ] ; 2016.
Abstract
In the title copper(II) complex, the metal atom is coordinated by two N atoms and two O atoms from two bidentate (
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DOI: 10.1107/S205698901601080X
PubMed: 27536389
PubMed Central: 4971848
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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 (<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><affiliation><nlm:aff id="a">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></nlm:aff></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:aff id="a">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></nlm:aff></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:aff id="b">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></nlm:aff></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:aff id="c">Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg,<country>Switzerland</country></nlm:aff></affiliation></author><author><name sortKey="Touzani, Rachid" sort="Touzani, Rachid" uniqKey="Touzani R" first="Rachid" last="Touzani">Rachid Touzani</name><affiliation><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></affiliation><affiliation><nlm:aff id="e">Faculté Pluridisciplinaire Nador BP 300, Selouane 62702, Nador,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Bailly, Corinne" sort="Bailly, Corinne" uniqKey="Bailly C" first="Corinne" last="Bailly">Corinne Bailly</name><affiliation><nlm:aff id="f">Service de Radiocristallographie, Institut de Chimie, Université de Strasbourg, UMR 7177, 67008 Strasbourg Cedex,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Crochet, Aurelien" sort="Crochet, Aurelien" uniqKey="Crochet A" first="Aurélien" last="Crochet">Aurélien Crochet</name><affiliation><nlm:aff id="g">Fribourg Center for Nanomaterials, FriMat, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg,<country>Switzerland</country></nlm:aff></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:aff id="c">Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg,<country>Switzerland</country></nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">27536389</idno><idno type="pmc">4971848</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4971848</idno><idno type="RBID">PMC:4971848</idno><idno type="doi">10.1107/S205698901601080X</idno><date when="2016">2016</date><idno type="wicri:Area/Pmc/Corpus">000006</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000006</idno></publicationStmt><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><affiliation><nlm:aff id="a">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></nlm:aff></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:aff id="a">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></nlm:aff></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:aff id="b">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></nlm:aff></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:aff id="c">Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg,<country>Switzerland</country></nlm:aff></affiliation></author><author><name sortKey="Touzani, Rachid" sort="Touzani, Rachid" uniqKey="Touzani R" first="Rachid" last="Touzani">Rachid Touzani</name><affiliation><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></affiliation><affiliation><nlm:aff id="e">Faculté Pluridisciplinaire Nador BP 300, Selouane 62702, Nador,<country>Morocco</country></nlm:aff></affiliation></author><author><name sortKey="Bailly, Corinne" sort="Bailly, Corinne" uniqKey="Bailly C" first="Corinne" last="Bailly">Corinne Bailly</name><affiliation><nlm:aff id="f">Service de Radiocristallographie, Institut de Chimie, Université de Strasbourg, UMR 7177, 67008 Strasbourg Cedex,<country>France</country></nlm:aff></affiliation></author><author><name sortKey="Crochet, Aurelien" sort="Crochet, Aurelien" uniqKey="Crochet A" first="Aurélien" last="Crochet">Aurélien Crochet</name><affiliation><nlm:aff id="g">Fribourg Center for Nanomaterials, FriMat, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg,<country>Switzerland</country></nlm:aff></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:aff id="c">Chemistry Department, University of Fribourg, Chemin du Musee 9, CH-1700 Fribourg,<country>Switzerland</country></nlm:aff></affiliation></author></analytic><series><title level="j">Acta Crystallographica Section E: Crystallographic Communications</title><idno type="eISSN">2056-9890</idno><imprint><date when="2016">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><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></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI><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
<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
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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><body><sec id="sec1"><title>Chemical context </title><p>Recently, 1-phenylazo-2-naphthol derivatives have attracted attention because the phenylazo-naphtholate group can provide <italic>N</italic>,<italic>O</italic>-bidentate chelation to stabilize transition or main group metal complexes. Azo-metal chelates have also attracted increasing attention due to their interesting electronic and geometrical features in connection with their applications in molecular memory storage, non-linear optical elements and printing systems. Another advantage of complexes involving azo DNO’s (dyes and pigments) and transition metal ions is the possibility to obtain new compounds with biological activity (Thomas <italic>et al.</italic>, 2004<xref ref-type="bibr" rid="bb25"> ▸</xref>; Reed <italic>et al.</italic>, 2006<xref ref-type="bibr" rid="bb19"> ▸</xref>). Transition metals have also been used in the treatment of several diseases, as metal complexes which are capable of cleaving DNA under physiological conditions are of interest in the development of metal-based anticancer agents. This is an impetus for chemists to develop innovative strategies for the preparation of more effective, target-specific and preferably non-covalently bound anticancer drugs (Chen <italic>et al.</italic>, 2010<xref ref-type="bibr" rid="bb11"> ▸</xref>; Cvek <italic>et al.</italic>, 2008<xref ref-type="bibr" rid="bb8"> ▸</xref>).<chem-struct id="scheme1"><graphic xlink:href="e-72-01093-scheme1.jpg" position="float"></graphic></chem-struct></p><p>Being interested in the synthesis and preparation of metal complexes bearing such ligands, we have successfully synthesized and structurally characterized Cu<sup>II</sup> complexes with <italic>N</italic>,<italic>O</italic>-bidentate phenylazo-naphtholate ligands (Chetioui <italic>et al.</italic>, 2015<italic>a</italic><xref ref-type="bibr" rid="bb6"> ▸</xref>,<italic>b</italic><xref ref-type="bibr" rid="bb7"> ▸</xref>). In this work we are involved in the colour-generation mechanism of azo pigments typically characterized by the chromophore of the azo group (–N=N–) (Chetioui <italic>et al.</italic>, 2013<italic>c</italic><xref ref-type="bibr" rid="bb4"> ▸</xref>,<italic>d</italic><xref ref-type="bibr" rid="bb5"> ▸</xref>) in order to synthesize new complexes with Cu(OAc)<sub>2</sub>·H<sub>2</sub>O, Ni(OAc)<sub>2</sub>·H<sub>2</sub>O, and Pd(OAc)<sub>2</sub>·H<sub>2</sub>O. We report herein on the synthesis and crystal structures of the title complexes, (I)–(III), of the ligand (<italic>E</italic>)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol, whose crystal structure has been described previously (Chetioui <italic>et al.</italic>, 2013<italic>c</italic><xref ref-type="bibr" rid="bb4"> ▸</xref>).</p></sec><sec id="sec2"><title>Structural commentary </title><p>In all three compounds the ligand (<italic>E</italic>)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol (Chetioui <italic>et al.</italic>, 2013<italic>c</italic><xref ref-type="bibr" rid="bb4"> ▸</xref>) coordinates in a <italic>N</italic>,<italic>O</italic>-bidentate manner. The metal atoms are coordinated by two oxygen atoms in a <italic>trans</italic> position of the C—O<sup>−</sup> function and two nitrogen atoms in a <italic>trans</italic> position of the N=N function. In compound (I)<xref ref-type="chem" rid="scheme1"></xref>, Fig. 1<xref ref-type="fig" rid="fig1"> ▸</xref>, the values of the angles involving the copper and the two oxygen and two nitrogen atoms (Table 1<xref ref-type="table" rid="table1"> ▸</xref>) indicate that the geometry of the coordination polyhedron is distorted square-planar. It has a τ<sub>4</sub> value of 0.15 [Yang <italic>et al.</italic>, 2007<xref ref-type="bibr" rid="bb26"> ▸</xref>; extreme configurations: 0.00 for square-pyramidal (SQP) and 1.00 for tetrahedral (TET); 0.85 for trigonal–pyramidal (TRP)]. In one of the ligands, the tribromobenzene ring (C17–C22) is inclined to the naphthalene ring system (C23–C32) by 37.4 (5)°, creating a weak intramolecular Cu⋯Br interaction [Cu1⋯Br4 = 3.134 (2) Å]. In the other ligand, the tribromobenzene ring (C1–C6) is almost normal to the naphthalene ring system (C7-C16), making a dihedral angle of 72.1 (6)°. A similar short intramolecular metal–halogen contact has been observed in the centrosymmetric complex bis(1-[(<italic>E</italic>)-(2-chlorophenyl)diazenyl]naphthalen-2-olato)copper(II), <italic>viz.</italic> Cu⋯Cl = 3.153 (1) Å (Benaouida <italic>et al.</italic>, 2013<xref ref-type="bibr" rid="bb3"> ▸</xref>), and the chlorobenzene ring is inclined to the naphthalene ring system by 32.72 (12)°.</p><p>Compounds (II)<xref ref-type="chem" rid="scheme1"></xref> and (III)<xref ref-type="chem" rid="scheme1"></xref>, the nickel(II) (Fig. 2<xref ref-type="fig" rid="fig2"> ▸</xref>, Table 2<xref ref-type="table" rid="table2"> ▸</xref>) and palladium(II) (Fig. 3<xref ref-type="fig" rid="fig3"> ▸</xref>, Table 3<xref ref-type="table" rid="table3"> ▸</xref>) complexes, respectively, are isotypic. The metal atoms are each located on inversion centres, coordinating in a bidentate fashion to the N and O atoms of the ligand, hence the metal coordination spheres have perfect square-planar geometry. The tribromobenzene rings (C1–C6) are almost normal to the naphthalene ring systems (C7–C16) with a dihedral angle of 80.79 (18)° in (II)<xref ref-type="chem" rid="scheme1"></xref> and 80.8 (3)° in (III)<xref ref-type="chem" rid="scheme1"></xref>.</p></sec><sec id="sec3"><title>Supramolecular features </title><p>As shown in Fig. 4<xref ref-type="fig" rid="fig4"> ▸</xref>, in the crystal of compound (I)<xref ref-type="chem" rid="scheme1"></xref>, molecules are linked by C—H⋯Br hydrogen bonds, forming chains along [001]. The chains are linked by C—H⋯π interactions, forming sheets lying parallel to (011). Details of these interactions are given in Table 4<xref ref-type="table" rid="table4"> ▸</xref>.</p><p>The crystal packing in compound (II)<xref ref-type="chem" rid="scheme1"></xref> [and isotypic compound (III)<xref ref-type="chem" rid="scheme1"></xref>] is illustrated in Fig. 5<xref ref-type="fig" rid="fig5"> ▸</xref>. Molecules are linked by C—H⋯π interactions, forming slabs lying parallel to (10<inline-formula><inline-graphic xlink:href="e-72-01093-efi1.jpg" mimetype="image" mime-subtype="gif"></inline-graphic></inline-formula>). Details of the intermolecular interactions are given in Table 5<xref ref-type="table" rid="table5"> ▸</xref> for (II)<xref ref-type="chem" rid="scheme1"></xref> and Table 6<xref ref-type="table" rid="table6"> ▸</xref> for (III)<xref ref-type="chem" rid="scheme1"></xref>.</p></sec><sec id="sec4"><title>Database survey </title><p>In the title ligand (<italic>E</italic>)-1-[(2,4,6-tribromophenyl)diazenyl]naphthalen-2-ol (CSD refcode AFOFIM; Chetioui <italic>et al.</italic>, 2013<italic>c</italic><xref ref-type="bibr" rid="bb4"> ▸</xref>) the benzene ring is inclined to the naphthalene ring system by 33.80 (16)°. A search of the Cambridge Structural Database (Version 5.37, update February 2016; Groom <italic>et al.</italic>, 2016<xref ref-type="bibr" rid="bb12"> ▸</xref>) for square-planar metal complexes of (<italic>E</italic>)-1-(phenyldiazenyl)naphthalen-2-ol and its derivatives gave seven hits (Fig. 6<xref ref-type="fig" rid="fig6"> ▸</xref>). They include a zinc(II) complex of the ligand (<italic>E</italic>)-1-(phenyldiazenyl)naphthalen-2-ol (LUQQIZ; Gallegos <italic>et al.</italic>, 2015<xref ref-type="bibr" rid="bb10"> ▸</xref>), where the zinc atom has a distorted trigonal–pyramidal configuration with a τ<sub>4</sub> parameter of 0.77. In the two ligands, the phenyl rings are inclined to the naphthalene ring systems by 11.4 (2) and 9.2 (3)°. Among the other six complexes, in which the metal atoms are all located on inversion centres, there are three copper(II) complexes with the ligands (<italic>E</italic>)-1-(phenyldiazenyl)naphthalen-2-ol (refcode CBANAP; Jarvis, 1961<xref ref-type="bibr" rid="bb13"> ▸</xref>), (<italic>E</italic>)-1-(2-chlorophenyl)diazenyl]naphthalen-2-ol (AFATIM; Benaouida <italic>et al.</italic>, 2013<xref ref-type="bibr" rid="bb3"> ▸</xref>) and (<italic>E</italic>)-1-(2,4-dimethylphenyl)diazenyl]naphthalen-2-ol (NOTNOB; Ferreira <italic>et al.</italic>, 2015<xref ref-type="bibr" rid="bb9"> ▸</xref>); two nickel complexes with the ligands (<italic>E</italic>)-1-(phenyldiazenyl)naphthalen-2-ol (NOTNUH; Ferreira <italic>et al.</italic>, 2015<xref ref-type="bibr" rid="bb9"> ▸</xref>) and (<italic>E</italic>)-1-(3-methylphenyl)diazenyl]naphthalen-2-ol (TOAZNI; Alcock <italic>et al.</italic>, 1968<xref ref-type="bibr" rid="bb1"> ▸</xref>); and one palladium complex with the ligand [(<italic>E</italic>)-1-(2-methylphenyl)diazenyl]naphthalen-2-ol (DURRIS; Lin <italic>et al.</italic>, 2010<xref ref-type="bibr" rid="bb14"> ▸</xref>). The orientation of the phenyl/benzene ring with respect to the naphthalene ring system varies quite considerably. In the palladium complex (DURRIS) and the copper complex (NOTNOB), where the benzene ring has a methyl group in the <italic>ortho</italic> position, the benzene ring is inclined to the naphthalene ring system by 74.41 (4) and 83.87 (6)°, respectively. In the other four complexes, the corresponding dihedral angles are 19.12 and 32.72 (12)° for the copper complexes CBANAP and AFATIM, respectively, and 24.06 (15) and <italic>ca</italic> 35.56° for the nickel complexes NOTNUH and TOAZNI, respectively.</p></sec><sec id="sec5"><title>Synthesis and crystallization </title><p>The title compounds were synthesized by the following procedure: (<italic>E</italic>)-1-[(2,4,6-tribromophenyl)diazenyl]-naphthalen-2-ol (2.0 mmol) and <italic>M</italic>(OAc)<sub>2</sub>·H<sub>2</sub>O (1.0 mmol; where <italic>M</italic> = Cu, Ni, Pd) was stirred at 298 K in a mixture of THF/MeOH (10/10 ml) for 24 h. The solvents were removed under vacuum and the residue was washed twice with hexane to give dark solids. The resulting solids were crystallized from CH<sub>2</sub>Cl<sub>2</sub> to yield red block-like crystals for (I)<xref ref-type="chem" rid="scheme1"></xref>, black prismatic crystals for (II)<xref ref-type="chem" rid="scheme1"></xref> and dark-red plate-like crystals for (III)<xref ref-type="chem" rid="scheme1"></xref>.</p></sec><sec id="sec6"><title>Refinement details </title><p>Crystal data, data collection and structure refinement details are summarized in Table 7<xref ref-type="table" rid="table7"> ▸</xref>. For all three compounds the C-bound H atoms were included in calculated positions and refined as riding: C—H = 0.95 Å for (I)<xref ref-type="chem" rid="scheme1"></xref> and (II)<xref ref-type="chem" rid="scheme1"></xref> and 0.93 Å for (III)<xref ref-type="chem" rid="scheme1"></xref>, with <italic>U</italic><sub>iso</sub>(H) = 1.2<italic>U</italic><sub>eq</sub>(C). For the copper(II) complex (I)<xref ref-type="chem" rid="scheme1"></xref>, 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>). The formula mass and unit-cell characteristics of the disordered solvent molecules were not taken into account during refinement. This complex crystallizes in the monoclinic space group <italic>P</italic>2<sub>1</sub>, with the Flack parameter = −0.006 (14).</p></sec><sec sec-type="supplementary-material"><title>Supplementary Material</title><supplementary-material content-type="local-data"><p>Crystal structure: contains datablock(s) global, I, II, III. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S205698901601080X/su5299sup1.cif">10.1107/S205698901601080X/su5299sup1.cif</ext-link></p><media mimetype="chemical" mime-subtype="x-cif" xlink:href="e-72-01093-sup1.cif" xlink:type="simple" id="d36e241" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) I. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S205698901601080X/su5299Isup3.hkl">10.1107/S205698901601080X/su5299Isup3.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-72-01093-Isup3.hkl" xlink:type="simple" id="d36e248" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) II. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S205698901601080X/su5299IIsup4.hkl">10.1107/S205698901601080X/su5299IIsup4.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-72-01093-IIsup4.hkl" xlink:type="simple" id="d36e255" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><p>Structure factors: contains datablock(s) III. DOI: <ext-link ext-link-type="uri" xlink:href="http://dx.doi.org/10.1107/S205698901601080X/su5299IIIsup2.hkl">10.1107/S205698901601080X/su5299IIIsup2.hkl</ext-link></p><media mimetype="text" mime-subtype="plain" xlink:href="e-72-01093-IIIsup2.hkl" xlink:type="simple" id="d36e262" position="anchor"></media></supplementary-material><supplementary-material content-type="local-data"><p>CCDC references: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1490056">1490056</ext-link>, <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1490055">1490055</ext-link>, <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1490054">1490054</ext-link></p></supplementary-material><supplementary-material content-type="local-data"><p>Additional supporting information: <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendsupfiles?su5299&file=su5299sup0.html&mime=text/html">crystallographic information</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/sendcif?su5299sup1&Qmime=cif">3D view</ext-link>; <ext-link ext-link-type="uri" xlink:href="http://scripts.iucr.org/cgi-bin/paper?su5299&checkcif=yes">checkCIF report</ext-link></p></supplementary-material></sec></body><back><ack><p>The authors are grateful to the Algerian Ministry of Higher Education and Scientific Research, the Algerian Directorate General for Scientific Research and Technological Development, and the University of Constantine for financial support.</p></ack><app-group><app><title>supplementary crystallographic information</title><sec id="tablewrapcrystaldatalong"><title>Crystal data</title><table-wrap position="anchor" id="d1e34"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">[Pd(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"><italic>F</italic>(000) = 1016</td></tr><tr><td rowspan="1" colspan="1"><italic>M</italic><italic><sub>r</sub></italic> = 1074.35</td><td rowspan="1" colspan="1"><italic>D</italic><sub>x</sub> = 2.142 Mg m<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">Monoclinic, <italic>P</italic>2<sub>1</sub>/<italic>n</italic></td><td rowspan="1" colspan="1">Cu <italic>K</italic>α radiation, λ = 1.54186 Å</td></tr><tr><td rowspan="1" colspan="1"><italic>a</italic> = 11.1896 (8) Å</td><td rowspan="1" colspan="1">Cell parameters from 3651 reflections</td></tr><tr><td rowspan="1" colspan="1"><italic>b</italic> = 12.4540 (8) Å</td><td rowspan="1" colspan="1">θ = 2.1–22.3°</td></tr><tr><td rowspan="1" colspan="1"><italic>c</italic> = 12.5511 (9) Å</td><td rowspan="1" colspan="1">µ = 13.23 mm<sup>−</sup><sup>1</sup></td></tr><tr><td rowspan="1" colspan="1">β = 107.749 (5)°</td><td rowspan="1" colspan="1"><italic>T</italic> = 200 K</td></tr><tr><td rowspan="1" colspan="1"><italic>V</italic> = 1665.8 (2) Å<sup>3</sup></td><td rowspan="1" colspan="1">Square plate, dark red</td></tr><tr><td rowspan="1" colspan="1"><italic>Z</italic> = 2</td><td rowspan="1" colspan="1">0.12 × 0.09 × 0.03 mm</td></tr></table></table-wrap></sec><sec id="tablewrapdatacollectionlong"><title>Data collection</title><table-wrap position="anchor" id="d1e164"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">STOE IPDS 2T diffractometer</td><td rowspan="1" colspan="1">2895 independent reflections</td></tr><tr><td rowspan="1" colspan="1">Radiation source: Genix-Cu,3D</td><td rowspan="1" colspan="1">2371 reflections with <italic>I</italic> > 2σ(<italic>I</italic>)</td></tr><tr><td rowspan="1" colspan="1">Graphite monochromator</td><td rowspan="1" colspan="1"><italic>R</italic><sub>int</sub> = 0.142</td></tr><tr><td rowspan="1" colspan="1">Detector resolution: 6.67 pixels mm<sup>-1</sup></td><td rowspan="1" colspan="1">θ<sub>max</sub> = 67.7°, θ<sub>min</sub> = 5.5°</td></tr><tr><td rowspan="1" colspan="1">rotation method scans</td><td rowspan="1" colspan="1"><italic>h</italic> = −13→12</td></tr><tr><td rowspan="1" colspan="1">Absorption correction: multi-scan (MULABS; Spek, 2009)</td><td rowspan="1" colspan="1"><italic>k</italic> = −14→14</td></tr><tr><td rowspan="1" colspan="1"><italic>T</italic><sub>min</sub> = 0.360, <italic>T</italic><sub>max</sub> = 1.000</td><td rowspan="1" colspan="1"><italic>l</italic> = −14→15</td></tr><tr><td rowspan="1" colspan="1">13003 measured reflections</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewraprefinementdatalong"><title>Refinement</title><table-wrap position="anchor" id="d1e279"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="2"><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">Refinement on <italic>F</italic><sup>2</sup></td><td rowspan="1" colspan="1">Secondary atom site location: difference Fourier map</td></tr><tr><td rowspan="1" colspan="1">Least-squares matrix: full</td><td rowspan="1" colspan="1">Hydrogen site location: inferred from neighbouring sites</td></tr><tr><td rowspan="1" colspan="1"><italic>R</italic>[<italic>F</italic><sup>2</sup> > 2σ(<italic>F</italic><sup>2</sup>)] = 0.057</td><td rowspan="1" colspan="1">H-atom parameters constrained</td></tr><tr><td rowspan="1" colspan="1"><italic>wR</italic>(<italic>F</italic><sup>2</sup>) = 0.170</td><td rowspan="1" colspan="1"><italic>w</italic> = 1/[σ<sup>2</sup>(<italic>F</italic><sub>o</sub><sup>2</sup>) + (0.1019<italic>P</italic>)<sup>2</sup> + 0.8121<italic>P</italic>] where <italic>P</italic> = (<italic>F</italic><sub>o</sub><sup>2</sup> + 2<italic>F</italic><sub>c</sub><sup>2</sup>)/3</td></tr><tr><td rowspan="1" colspan="1"><italic>S</italic> = 1.11</td><td rowspan="1" colspan="1">(Δ/σ)<sub>max</sub> < 0.001</td></tr><tr><td rowspan="1" colspan="1">2895 reflections</td><td rowspan="1" colspan="1">Δρ<sub>max</sub> = 0.88 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">206 parameters</td><td rowspan="1" colspan="1">Δρ<sub>min</sub> = −1.10 e Å<sup>−</sup><sup>3</sup></td></tr><tr><td rowspan="1" colspan="1">0 restraints</td><td rowspan="1" colspan="1">Extinction correction: SHELXL, Fc<sup>*</sup>=kFc[1+0.001xFc<sup>2</sup>λ<sup>3</sup>/sin(2θ)]<sup>-1/4</sup></td></tr><tr><td rowspan="1" colspan="1">Primary atom site location: structure-invariant direct methods</td><td rowspan="1" colspan="1">Extinction coefficient: 0.0040 (4)</td></tr></table></table-wrap></sec><sec id="specialdetails"><title>Special details</title><table-wrap position="anchor" id="d1e456"><table rules="all" frame="box" style="table-layout:fixed"><tr><td rowspan="1" colspan="1">Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.</td></tr></table></table-wrap></sec><sec id="tablewrapcoords"><title>Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e477"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"><italic>x</italic></td><td rowspan="1" colspan="1"><italic>y</italic></td><td rowspan="1" colspan="1"><italic>z</italic></td><td rowspan="1" colspan="1"><italic>U</italic><sub>iso</sub>*/<italic>U</italic><sub>eq</sub></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Br1</td><td rowspan="1" colspan="1">0.16311 (8)</td><td rowspan="1" colspan="1">0.39498 (7)</td><td rowspan="1" colspan="1">0.53262 (6)</td><td rowspan="1" colspan="1">0.0659 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Br2</td><td rowspan="1" colspan="1">0.33399 (8)</td><td rowspan="1" colspan="1">0.60480 (8)</td><td rowspan="1" colspan="1">0.20631 (7)</td><td rowspan="1" colspan="1">0.0737 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Br3</td><td rowspan="1" colspan="1">−0.07036 (8)</td><td rowspan="1" colspan="1">0.31295 (7)</td><td rowspan="1" colspan="1">0.07577 (7)</td><td rowspan="1" colspan="1">0.0754 (4)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">Pd1</td><td rowspan="1" colspan="1">0.5000</td><td rowspan="1" colspan="1">0.5000</td><td rowspan="1" colspan="1">0.5000</td><td rowspan="1" colspan="1">0.0456 (3)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.5428 (4)</td><td rowspan="1" colspan="1">0.6130 (4)</td><td rowspan="1" colspan="1">0.6155 (4)</td><td rowspan="1" colspan="1">0.0573 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.3223 (5)</td><td rowspan="1" colspan="1">0.5521 (4)</td><td rowspan="1" colspan="1">0.4432 (4)</td><td rowspan="1" colspan="1">0.0468 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.2730 (5)</td><td rowspan="1" colspan="1">0.6310 (4)</td><td rowspan="1" colspan="1">0.4798 (4)</td><td rowspan="1" colspan="1">0.0486 (12)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.2323 (6)</td><td rowspan="1" colspan="1">0.4941 (5)</td><td rowspan="1" colspan="1">0.3582 (5)</td><td rowspan="1" colspan="1">0.0471 (15)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.2246 (6)</td><td rowspan="1" colspan="1">0.5074 (5)</td><td rowspan="1" colspan="1">0.2447 (5)</td><td rowspan="1" colspan="1">0.0482 (15)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.1354 (7)</td><td rowspan="1" colspan="1">0.4532 (6)</td><td rowspan="1" colspan="1">0.1598 (5)</td><td rowspan="1" colspan="1">0.0563 (17)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H3</td><td rowspan="1" colspan="1">0.1311</td><td rowspan="1" colspan="1">0.4629</td><td rowspan="1" colspan="1">0.0836</td><td rowspan="1" colspan="1">0.068*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.0544 (7)</td><td rowspan="1" colspan="1">0.3855 (5)</td><td rowspan="1" colspan="1">0.1889 (6)</td><td rowspan="1" colspan="1">0.0532 (16)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.0597 (6)</td><td rowspan="1" colspan="1">0.3675 (5)</td><td rowspan="1" colspan="1">0.2996 (6)</td><td rowspan="1" colspan="1">0.0495 (15)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H5</td><td rowspan="1" colspan="1">0.0032</td><td rowspan="1" colspan="1">0.3195</td><td rowspan="1" colspan="1">0.3184</td><td rowspan="1" colspan="1">0.059*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.1513 (6)</td><td rowspan="1" colspan="1">0.4227 (5)</td><td rowspan="1" colspan="1">0.3817 (5)</td><td rowspan="1" colspan="1">0.0474 (14)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.3371 (6)</td><td rowspan="1" colspan="1">0.6961 (5)</td><td rowspan="1" colspan="1">0.5647 (5)</td><td rowspan="1" colspan="1">0.0464 (14)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.4672 (6)</td><td rowspan="1" colspan="1">0.6842 (6)</td><td rowspan="1" colspan="1">0.6279 (5)</td><td rowspan="1" colspan="1">0.0523 (15)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.5192 (7)</td><td rowspan="1" colspan="1">0.7634 (6)</td><td rowspan="1" colspan="1">0.7146 (6)</td><td rowspan="1" colspan="1">0.0570 (17)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H9</td><td rowspan="1" colspan="1">0.6039</td><td rowspan="1" colspan="1">0.7562</td><td rowspan="1" colspan="1">0.7601</td><td rowspan="1" colspan="1">0.068*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.4511 (7)</td><td rowspan="1" colspan="1">0.8468 (6)</td><td rowspan="1" colspan="1">0.7323 (6)</td><td rowspan="1" colspan="1">0.0604 (18)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H10</td><td rowspan="1" colspan="1">0.4904</td><td rowspan="1" colspan="1">0.8983</td><td rowspan="1" colspan="1">0.7877</td><td rowspan="1" colspan="1">0.072*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.3214 (7)</td><td rowspan="1" colspan="1">0.8605 (6)</td><td rowspan="1" colspan="1">0.6705 (6)</td><td rowspan="1" colspan="1">0.0536 (16)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.2640 (7)</td><td rowspan="1" colspan="1">0.7831 (5)</td><td rowspan="1" colspan="1">0.5895 (5)</td><td rowspan="1" colspan="1">0.0505 (15)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.1345 (7)</td><td rowspan="1" colspan="1">0.7932 (6)</td><td rowspan="1" colspan="1">0.5352 (6)</td><td rowspan="1" colspan="1">0.0583 (17)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H13</td><td rowspan="1" colspan="1">0.0933</td><td rowspan="1" colspan="1">0.7427</td><td rowspan="1" colspan="1">0.4793</td><td rowspan="1" colspan="1">0.070*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.0678 (8)</td><td rowspan="1" colspan="1">0.8748 (7)</td><td rowspan="1" colspan="1">0.5619 (7)</td><td rowspan="1" colspan="1">0.070 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H14</td><td rowspan="1" colspan="1">−0.0202</td><td rowspan="1" colspan="1">0.8783</td><td rowspan="1" colspan="1">0.5263</td><td rowspan="1" colspan="1">0.084*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.1257 (8)</td><td rowspan="1" colspan="1">0.9538 (7)</td><td rowspan="1" colspan="1">0.6406 (6)</td><td rowspan="1" colspan="1">0.071 (2)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H15</td><td rowspan="1" colspan="1">0.0780</td><td rowspan="1" colspan="1">1.0109</td><td rowspan="1" colspan="1">0.6573</td><td rowspan="1" colspan="1">0.085*</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.2509 (8)</td><td rowspan="1" colspan="1">0.9469 (7)</td><td rowspan="1" colspan="1">0.6922 (7)</td><td rowspan="1" colspan="1">0.0652 (19)</td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">H16</td><td rowspan="1" colspan="1">0.2917</td><td rowspan="1" colspan="1">1.0010</td><td rowspan="1" colspan="1">0.7438</td><td rowspan="1" colspan="1">0.078*</td><td rowspan="1" colspan="1"></td></tr></table></table-wrap></sec><sec id="tablewrapadps"><title>Atomic displacement parameters (Å<sup>2</sup>)</title><table-wrap position="anchor" id="d1e891"><table rules="all" frame="box" style="table-layout:fixed" summary=""><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"><italic>U</italic><sup>11</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>22</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>33</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>12</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>13</sup></td><td rowspan="1" colspan="1"><italic>U</italic><sup>23</sup></td></tr><tr><td rowspan="1" colspan="1">Br1</td><td rowspan="1" colspan="1">0.0649 (6)</td><td rowspan="1" colspan="1">0.0817 (6)</td><td rowspan="1" colspan="1">0.0436 (5)</td><td rowspan="1" colspan="1">−0.0081 (4)</td><td rowspan="1" colspan="1">0.0055 (4)</td><td rowspan="1" colspan="1">0.0092 (3)</td></tr><tr><td rowspan="1" colspan="1">Br2</td><td rowspan="1" colspan="1">0.0614 (6)</td><td rowspan="1" colspan="1">0.0997 (7)</td><td rowspan="1" colspan="1">0.0531 (5)</td><td rowspan="1" colspan="1">−0.0261 (4)</td><td rowspan="1" colspan="1">0.0070 (4)</td><td rowspan="1" colspan="1">0.0073 (4)</td></tr><tr><td rowspan="1" colspan="1">Br3</td><td rowspan="1" colspan="1">0.0648 (6)</td><td rowspan="1" colspan="1">0.0834 (6)</td><td rowspan="1" colspan="1">0.0603 (6)</td><td rowspan="1" colspan="1">−0.0172 (4)</td><td rowspan="1" colspan="1">−0.0073 (4)</td><td rowspan="1" colspan="1">−0.0226 (4)</td></tr><tr><td rowspan="1" colspan="1">Pd1</td><td rowspan="1" colspan="1">0.0353 (4)</td><td rowspan="1" colspan="1">0.0550 (4)</td><td rowspan="1" colspan="1">0.0369 (4)</td><td rowspan="1" colspan="1">−0.0014 (3)</td><td rowspan="1" colspan="1">−0.0032 (3)</td><td rowspan="1" colspan="1">−0.0038 (3)</td></tr><tr><td rowspan="1" colspan="1">O1</td><td rowspan="1" colspan="1">0.042 (3)</td><td rowspan="1" colspan="1">0.065 (3)</td><td rowspan="1" colspan="1">0.052 (3)</td><td rowspan="1" colspan="1">0.003 (2)</td><td rowspan="1" colspan="1">−0.005 (2)</td><td rowspan="1" colspan="1">−0.009 (2)</td></tr><tr><td rowspan="1" colspan="1">N1</td><td rowspan="1" colspan="1">0.042 (3)</td><td rowspan="1" colspan="1">0.053 (3)</td><td rowspan="1" colspan="1">0.037 (3)</td><td rowspan="1" colspan="1">−0.007 (2)</td><td rowspan="1" colspan="1">−0.001 (2)</td><td rowspan="1" colspan="1">−0.004 (2)</td></tr><tr><td rowspan="1" colspan="1">N2</td><td rowspan="1" colspan="1">0.040 (3)</td><td rowspan="1" colspan="1">0.054 (3)</td><td rowspan="1" colspan="1">0.042 (3)</td><td rowspan="1" colspan="1">−0.004 (2)</td><td rowspan="1" colspan="1">−0.003 (2)</td><td rowspan="1" colspan="1">0.000 (2)</td></tr><tr><td rowspan="1" colspan="1">C1</td><td rowspan="1" colspan="1">0.038 (3)</td><td rowspan="1" colspan="1">0.054 (3)</td><td rowspan="1" colspan="1">0.037 (3)</td><td rowspan="1" colspan="1">0.007 (3)</td><td rowspan="1" colspan="1">−0.007 (3)</td><td rowspan="1" colspan="1">0.001 (3)</td></tr><tr><td rowspan="1" colspan="1">C2</td><td rowspan="1" colspan="1">0.036 (3)</td><td rowspan="1" colspan="1">0.061 (4)</td><td rowspan="1" colspan="1">0.037 (3)</td><td rowspan="1" colspan="1">0.000 (3)</td><td rowspan="1" colspan="1">−0.005 (3)</td><td rowspan="1" colspan="1">0.002 (3)</td></tr><tr><td rowspan="1" colspan="1">C3</td><td rowspan="1" colspan="1">0.049 (4)</td><td rowspan="1" colspan="1">0.073 (4)</td><td rowspan="1" colspan="1">0.038 (3)</td><td rowspan="1" colspan="1">0.004 (3)</td><td rowspan="1" colspan="1">−0.001 (3)</td><td rowspan="1" colspan="1">−0.001 (3)</td></tr><tr><td rowspan="1" colspan="1">C4</td><td rowspan="1" colspan="1">0.045 (4)</td><td rowspan="1" colspan="1">0.056 (4)</td><td rowspan="1" colspan="1">0.048 (4)</td><td rowspan="1" colspan="1">−0.005 (3)</td><td rowspan="1" colspan="1">−0.002 (3)</td><td rowspan="1" colspan="1">−0.005 (3)</td></tr><tr><td rowspan="1" colspan="1">C5</td><td rowspan="1" colspan="1">0.043 (4)</td><td rowspan="1" colspan="1">0.047 (3)</td><td rowspan="1" colspan="1">0.054 (4)</td><td rowspan="1" colspan="1">−0.002 (3)</td><td rowspan="1" colspan="1">0.008 (3)</td><td rowspan="1" colspan="1">0.002 (3)</td></tr><tr><td rowspan="1" colspan="1">C6</td><td rowspan="1" colspan="1">0.042 (3)</td><td rowspan="1" colspan="1">0.049 (3)</td><td rowspan="1" colspan="1">0.040 (3)</td><td rowspan="1" colspan="1">−0.002 (3)</td><td rowspan="1" colspan="1">−0.003 (3)</td><td rowspan="1" colspan="1">0.000 (3)</td></tr><tr><td rowspan="1" colspan="1">C7</td><td rowspan="1" colspan="1">0.035 (3)</td><td rowspan="1" colspan="1">0.057 (3)</td><td rowspan="1" colspan="1">0.042 (3)</td><td rowspan="1" colspan="1">−0.001 (3)</td><td rowspan="1" colspan="1">0.004 (3)</td><td rowspan="1" colspan="1">−0.005 (3)</td></tr><tr><td rowspan="1" colspan="1">C8</td><td rowspan="1" colspan="1">0.045 (4)</td><td rowspan="1" colspan="1">0.063 (4)</td><td rowspan="1" colspan="1">0.040 (3)</td><td rowspan="1" colspan="1">−0.007 (3)</td><td rowspan="1" colspan="1">0.001 (3)</td><td rowspan="1" colspan="1">0.001 (3)</td></tr><tr><td rowspan="1" colspan="1">C9</td><td rowspan="1" colspan="1">0.046 (4)</td><td rowspan="1" colspan="1">0.070 (4)</td><td rowspan="1" colspan="1">0.047 (4)</td><td rowspan="1" colspan="1">−0.004 (3)</td><td rowspan="1" colspan="1">0.002 (3)</td><td rowspan="1" colspan="1">−0.012 (3)</td></tr><tr><td rowspan="1" colspan="1">C10</td><td rowspan="1" colspan="1">0.059 (4)</td><td rowspan="1" colspan="1">0.070 (4)</td><td rowspan="1" colspan="1">0.043 (4)</td><td rowspan="1" colspan="1">−0.014 (4)</td><td rowspan="1" colspan="1">0.002 (3)</td><td rowspan="1" colspan="1">−0.010 (3)</td></tr><tr><td rowspan="1" colspan="1">C11</td><td rowspan="1" colspan="1">0.053 (4)</td><td rowspan="1" colspan="1">0.060 (4)</td><td rowspan="1" colspan="1">0.046 (4)</td><td rowspan="1" colspan="1">0.001 (3)</td><td rowspan="1" colspan="1">0.012 (3)</td><td rowspan="1" colspan="1">−0.002 (3)</td></tr><tr><td rowspan="1" colspan="1">C12</td><td rowspan="1" colspan="1">0.048 (4)</td><td rowspan="1" colspan="1">0.057 (4)</td><td rowspan="1" colspan="1">0.043 (3)</td><td rowspan="1" colspan="1">−0.007 (3)</td><td rowspan="1" colspan="1">0.008 (3)</td><td rowspan="1" colspan="1">−0.001 (3)</td></tr><tr><td rowspan="1" colspan="1">C13</td><td rowspan="1" colspan="1">0.046 (4)</td><td rowspan="1" colspan="1">0.070 (4)</td><td rowspan="1" colspan="1">0.052 (4)</td><td rowspan="1" colspan="1">0.000 (3)</td><td rowspan="1" colspan="1">0.004 (3)</td><td rowspan="1" colspan="1">−0.010 (3)</td></tr><tr><td rowspan="1" colspan="1">C14</td><td rowspan="1" colspan="1">0.056 (5)</td><td rowspan="1" colspan="1">0.080 (5)</td><td rowspan="1" colspan="1">0.064 (5)</td><td rowspan="1" colspan="1">0.002 (4)</td><td rowspan="1" colspan="1">0.004 (4)</td><td rowspan="1" colspan="1">−0.003 (4)</td></tr><tr><td rowspan="1" colspan="1">C15</td><td rowspan="1" colspan="1">0.074 (6)</td><td rowspan="1" colspan="1">0.072 (5)</td><td rowspan="1" colspan="1">0.060 (5)</td><td rowspan="1" colspan="1">0.019 (4)</td><td rowspan="1" colspan="1">0.009 (4)</td><td rowspan="1" colspan="1">0.001 (4)</td></tr><tr><td rowspan="1" colspan="1">C16</td><td rowspan="1" colspan="1">0.069 (5)</td><td rowspan="1" colspan="1">0.065 (4)</td><td rowspan="1" colspan="1">0.057 (4)</td><td rowspan="1" colspan="1">−0.002 (4)</td><td rowspan="1" colspan="1">0.013 (4)</td><td rowspan="1" colspan="1">0.002 (4)</td></tr></table></table-wrap></sec><sec id="tablewrapgeomlong"><title>Geometric parameters (Å, º)</title><table-wrap position="anchor" id="d1e1358"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="4"><col span="1"></col><col span="1"></col><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1">Br1—C6</td><td rowspan="1" colspan="1">1.889 (6)</td><td rowspan="1" colspan="1">C5—H5</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">Br2—C2</td><td rowspan="1" colspan="1">1.887 (7)</td><td rowspan="1" colspan="1">C7—C8</td><td rowspan="1" colspan="1">1.437 (9)</td></tr><tr><td rowspan="1" colspan="1">Br3—C4</td><td rowspan="1" colspan="1">1.890 (7)</td><td rowspan="1" colspan="1">C7—C12</td><td rowspan="1" colspan="1">1.448 (9)</td></tr><tr><td rowspan="1" colspan="1">Pd1—O1</td><td rowspan="1" colspan="1">1.972 (5)</td><td rowspan="1" colspan="1">C8—C9</td><td rowspan="1" colspan="1">1.452 (10)</td></tr><tr><td rowspan="1" colspan="1">Pd1—O1<sup>i</sup></td><td rowspan="1" colspan="1">1.972 (5)</td><td rowspan="1" colspan="1">C9—C10</td><td rowspan="1" colspan="1">1.346 (10)</td></tr><tr><td rowspan="1" colspan="1">Pd1—N1<sup>i</sup></td><td rowspan="1" colspan="1">2.004 (5)</td><td rowspan="1" colspan="1">C9—H9</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">Pd1—N1</td><td rowspan="1" colspan="1">2.004 (5)</td><td rowspan="1" colspan="1">C10—C11</td><td rowspan="1" colspan="1">1.432 (10)</td></tr><tr><td rowspan="1" colspan="1">O1—C8</td><td rowspan="1" colspan="1">1.268 (8)</td><td rowspan="1" colspan="1">C10—H10</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">N1—N2</td><td rowspan="1" colspan="1">1.279 (8)</td><td rowspan="1" colspan="1">C11—C12</td><td rowspan="1" colspan="1">1.406 (10)</td></tr><tr><td rowspan="1" colspan="1">N1—C1</td><td rowspan="1" colspan="1">1.422 (8)</td><td rowspan="1" colspan="1">C11—C16</td><td rowspan="1" colspan="1">1.409 (11)</td></tr><tr><td rowspan="1" colspan="1">N2—C7</td><td rowspan="1" colspan="1">1.356 (8)</td><td rowspan="1" colspan="1">C12—C13</td><td rowspan="1" colspan="1">1.406 (10)</td></tr><tr><td rowspan="1" colspan="1">C1—C6</td><td rowspan="1" colspan="1">1.365 (9)</td><td rowspan="1" colspan="1">C13—C14</td><td rowspan="1" colspan="1">1.362 (11)</td></tr><tr><td rowspan="1" colspan="1">C1—C2</td><td rowspan="1" colspan="1">1.410 (9)</td><td rowspan="1" colspan="1">C13—H13</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C2—C3</td><td rowspan="1" colspan="1">1.393 (9)</td><td rowspan="1" colspan="1">C14—C15</td><td rowspan="1" colspan="1">1.405 (12)</td></tr><tr><td rowspan="1" colspan="1">C3—C4</td><td rowspan="1" colspan="1">1.367 (10)</td><td rowspan="1" colspan="1">C14—H14</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C3—H3</td><td rowspan="1" colspan="1">0.9500</td><td rowspan="1" colspan="1">C15—C16</td><td rowspan="1" colspan="1">1.355 (11)</td></tr><tr><td rowspan="1" colspan="1">C4—C5</td><td rowspan="1" colspan="1">1.390 (10)</td><td rowspan="1" colspan="1">C15—H15</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1">C5—C6</td><td rowspan="1" colspan="1">1.394 (9)</td><td rowspan="1" colspan="1">C16—H16</td><td rowspan="1" colspan="1">0.9500</td></tr><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">O1—Pd1—O1<sup>i</sup></td><td rowspan="1" colspan="1">180.0</td><td rowspan="1" colspan="1">N2—C7—C12</td><td rowspan="1" colspan="1">114.7 (6)</td></tr><tr><td rowspan="1" colspan="1">O1—Pd1—N1<sup>i</sup></td><td rowspan="1" colspan="1">88.7 (2)</td><td rowspan="1" colspan="1">C8—C7—C12</td><td rowspan="1" colspan="1">120.1 (6)</td></tr><tr><td rowspan="1" colspan="1">O1<sup>i</sup>—Pd1—N1<sup>i</sup></td><td rowspan="1" colspan="1">91.3 (2)</td><td rowspan="1" colspan="1">O1—C8—C7</td><td rowspan="1" colspan="1">127.3 (6)</td></tr><tr><td rowspan="1" colspan="1">O1—Pd1—N1</td><td rowspan="1" colspan="1">91.3 (2)</td><td rowspan="1" colspan="1">O1—C8—C9</td><td rowspan="1" colspan="1">115.9 (6)</td></tr><tr><td rowspan="1" colspan="1">O1<sup>i</sup>—Pd1—N1</td><td rowspan="1" colspan="1">88.7 (2)</td><td rowspan="1" colspan="1">C7—C8—C9</td><td rowspan="1" colspan="1">116.8 (6)</td></tr><tr><td rowspan="1" colspan="1">N1<sup>i</sup>—Pd1—N1</td><td rowspan="1" colspan="1">180.0</td><td rowspan="1" colspan="1">C10—C9—C8</td><td rowspan="1" colspan="1">122.0 (7)</td></tr><tr><td rowspan="1" colspan="1">C8—O1—Pd1</td><td rowspan="1" colspan="1">124.6 (4)</td><td rowspan="1" colspan="1">C10—C9—H9</td><td rowspan="1" colspan="1">119.0</td></tr><tr><td rowspan="1" colspan="1">N2—N1—C1</td><td rowspan="1" colspan="1">112.0 (5)</td><td rowspan="1" colspan="1">C8—C9—H9</td><td rowspan="1" colspan="1">119.0</td></tr><tr><td rowspan="1" colspan="1">N2—N1—Pd1</td><td rowspan="1" colspan="1">127.7 (4)</td><td rowspan="1" colspan="1">C9—C10—C11</td><td rowspan="1" colspan="1">122.3 (6)</td></tr><tr><td rowspan="1" colspan="1">C1—N1—Pd1</td><td rowspan="1" colspan="1">120.1 (4)</td><td rowspan="1" colspan="1">C9—C10—H10</td><td rowspan="1" colspan="1">118.9</td></tr><tr><td rowspan="1" colspan="1">N1—N2—C7</td><td rowspan="1" colspan="1">123.9 (5)</td><td rowspan="1" colspan="1">C11—C10—H10</td><td rowspan="1" colspan="1">118.9</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C2</td><td rowspan="1" colspan="1">117.1 (6)</td><td rowspan="1" colspan="1">C12—C11—C16</td><td rowspan="1" colspan="1">120.3 (7)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—N1</td><td rowspan="1" colspan="1">122.3 (6)</td><td rowspan="1" colspan="1">C12—C11—C10</td><td rowspan="1" colspan="1">118.3 (6)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—N1</td><td rowspan="1" colspan="1">120.6 (6)</td><td rowspan="1" colspan="1">C16—C11—C10</td><td rowspan="1" colspan="1">121.4 (7)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—C1</td><td rowspan="1" colspan="1">121.7 (6)</td><td rowspan="1" colspan="1">C13—C12—C11</td><td rowspan="1" colspan="1">117.7 (6)</td></tr><tr><td rowspan="1" colspan="1">C3—C2—Br2</td><td rowspan="1" colspan="1">119.0 (5)</td><td rowspan="1" colspan="1">C13—C12—C7</td><td rowspan="1" colspan="1">121.9 (6)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—Br2</td><td rowspan="1" colspan="1">119.3 (5)</td><td rowspan="1" colspan="1">C11—C12—C7</td><td rowspan="1" colspan="1">120.4 (6)</td></tr><tr><td rowspan="1" colspan="1">C4—C3—C2</td><td rowspan="1" colspan="1">118.2 (6)</td><td rowspan="1" colspan="1">C14—C13—C12</td><td rowspan="1" colspan="1">120.6 (7)</td></tr><tr><td rowspan="1" colspan="1">C4—C3—H3</td><td rowspan="1" colspan="1">120.9</td><td rowspan="1" colspan="1">C14—C13—H13</td><td rowspan="1" colspan="1">119.7</td></tr><tr><td rowspan="1" colspan="1">C2—C3—H3</td><td rowspan="1" colspan="1">120.9</td><td rowspan="1" colspan="1">C12—C13—H13</td><td rowspan="1" colspan="1">119.7</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5</td><td rowspan="1" colspan="1">122.5 (6)</td><td rowspan="1" colspan="1">C13—C14—C15</td><td rowspan="1" colspan="1">121.7 (8)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—Br3</td><td rowspan="1" colspan="1">119.5 (5)</td><td rowspan="1" colspan="1">C13—C14—H14</td><td rowspan="1" colspan="1">119.1</td></tr><tr><td rowspan="1" colspan="1">C5—C4—Br3</td><td rowspan="1" colspan="1">118.0 (5)</td><td rowspan="1" colspan="1">C15—C14—H14</td><td rowspan="1" colspan="1">119.1</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6</td><td rowspan="1" colspan="1">117.2 (6)</td><td rowspan="1" colspan="1">C16—C15—C14</td><td rowspan="1" colspan="1">118.7 (8)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—H5</td><td rowspan="1" colspan="1">121.4</td><td rowspan="1" colspan="1">C16—C15—H15</td><td rowspan="1" colspan="1">120.7</td></tr><tr><td rowspan="1" colspan="1">C6—C5—H5</td><td rowspan="1" colspan="1">121.4</td><td rowspan="1" colspan="1">C14—C15—H15</td><td rowspan="1" colspan="1">120.7</td></tr><tr><td rowspan="1" colspan="1">C1—C6—C5</td><td rowspan="1" colspan="1">123.3 (6)</td><td rowspan="1" colspan="1">C15—C16—C11</td><td rowspan="1" colspan="1">120.9 (7)</td></tr><tr><td rowspan="1" colspan="1">C1—C6—Br1</td><td rowspan="1" colspan="1">119.2 (5)</td><td rowspan="1" colspan="1">C15—C16—H16</td><td rowspan="1" colspan="1">119.5</td></tr><tr><td rowspan="1" colspan="1">C5—C6—Br1</td><td rowspan="1" colspan="1">117.5 (5)</td><td rowspan="1" colspan="1">C11—C16—H16</td><td rowspan="1" colspan="1">119.5</td></tr><tr><td rowspan="1" colspan="1">N2—C7—C8</td><td rowspan="1" colspan="1">125.2 (6)</td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td><td rowspan="1" colspan="1"></td></tr><tr><td rowspan="1" colspan="1">C1—N1—N2—C7</td><td rowspan="1" colspan="1">176.7 (6)</td><td rowspan="1" colspan="1">Pd1—O1—C8—C9</td><td rowspan="1" colspan="1">−177.0 (5)</td></tr><tr><td rowspan="1" colspan="1">Pd1—N1—N2—C7</td><td rowspan="1" colspan="1">1.8 (9)</td><td rowspan="1" colspan="1">N2—C7—C8—O1</td><td rowspan="1" colspan="1">0.2 (11)</td></tr><tr><td rowspan="1" colspan="1">N2—N1—C1—C6</td><td rowspan="1" colspan="1">−77.8 (7)</td><td rowspan="1" colspan="1">C12—C7—C8—O1</td><td rowspan="1" colspan="1">−179.5 (6)</td></tr><tr><td rowspan="1" colspan="1">Pd1—N1—C1—C6</td><td rowspan="1" colspan="1">97.6 (6)</td><td rowspan="1" colspan="1">N2—C7—C8—C9</td><td rowspan="1" colspan="1">179.0 (6)</td></tr><tr><td rowspan="1" colspan="1">N2—N1—C1—C2</td><td rowspan="1" colspan="1">103.1 (7)</td><td rowspan="1" colspan="1">C12—C7—C8—C9</td><td rowspan="1" colspan="1">−0.7 (9)</td></tr><tr><td rowspan="1" colspan="1">Pd1—N1—C1—C2</td><td rowspan="1" colspan="1">−81.6 (6)</td><td rowspan="1" colspan="1">O1—C8—C9—C10</td><td rowspan="1" colspan="1">176.2 (7)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C2—C3</td><td rowspan="1" colspan="1">2.2 (9)</td><td rowspan="1" colspan="1">C7—C8—C9—C10</td><td rowspan="1" colspan="1">−2.7 (10)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C2—C3</td><td rowspan="1" colspan="1">−178.6 (6)</td><td rowspan="1" colspan="1">C8—C9—C10—C11</td><td rowspan="1" colspan="1">2.8 (11)</td></tr><tr><td rowspan="1" colspan="1">C6—C1—C2—Br2</td><td rowspan="1" colspan="1">−180.0 (5)</td><td rowspan="1" colspan="1">C9—C10—C11—C12</td><td rowspan="1" colspan="1">0.7 (11)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C2—Br2</td><td rowspan="1" colspan="1">−0.8 (8)</td><td rowspan="1" colspan="1">C9—C10—C11—C16</td><td rowspan="1" colspan="1">178.4 (7)</td></tr><tr><td rowspan="1" colspan="1">C1—C2—C3—C4</td><td rowspan="1" colspan="1">−0.1 (10)</td><td rowspan="1" colspan="1">C16—C11—C12—C13</td><td rowspan="1" colspan="1">−2.3 (10)</td></tr><tr><td rowspan="1" colspan="1">Br2—C2—C3—C4</td><td rowspan="1" colspan="1">−178.0 (5)</td><td rowspan="1" colspan="1">C10—C11—C12—C13</td><td rowspan="1" colspan="1">175.4 (7)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—C5</td><td rowspan="1" colspan="1">−1.4 (11)</td><td rowspan="1" colspan="1">C16—C11—C12—C7</td><td rowspan="1" colspan="1">178.2 (6)</td></tr><tr><td rowspan="1" colspan="1">C2—C3—C4—Br3</td><td rowspan="1" colspan="1">178.6 (5)</td><td rowspan="1" colspan="1">C10—C11—C12—C7</td><td rowspan="1" colspan="1">−4.1 (10)</td></tr><tr><td rowspan="1" colspan="1">C3—C4—C5—C6</td><td rowspan="1" colspan="1">0.8 (10)</td><td rowspan="1" colspan="1">N2—C7—C12—C13</td><td rowspan="1" colspan="1">4.8 (9)</td></tr><tr><td rowspan="1" colspan="1">Br3—C4—C5—C6</td><td rowspan="1" colspan="1">−179.2 (5)</td><td rowspan="1" colspan="1">C8—C7—C12—C13</td><td rowspan="1" colspan="1">−175.4 (6)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—C5</td><td rowspan="1" colspan="1">−2.9 (10)</td><td rowspan="1" colspan="1">N2—C7—C12—C11</td><td rowspan="1" colspan="1">−175.7 (6)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C6—C5</td><td rowspan="1" colspan="1">177.9 (6)</td><td rowspan="1" colspan="1">C8—C7—C12—C11</td><td rowspan="1" colspan="1">4.1 (9)</td></tr><tr><td rowspan="1" colspan="1">C2—C1—C6—Br1</td><td rowspan="1" colspan="1">176.4 (5)</td><td rowspan="1" colspan="1">C11—C12—C13—C14</td><td rowspan="1" colspan="1">−0.8 (11)</td></tr><tr><td rowspan="1" colspan="1">N1—C1—C6—Br1</td><td rowspan="1" colspan="1">−2.8 (8)</td><td rowspan="1" colspan="1">C7—C12—C13—C14</td><td rowspan="1" colspan="1">178.7 (7)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—C1</td><td rowspan="1" colspan="1">1.5 (10)</td><td rowspan="1" colspan="1">C12—C13—C14—C15</td><td rowspan="1" colspan="1">2.6 (13)</td></tr><tr><td rowspan="1" colspan="1">C4—C5—C6—Br1</td><td rowspan="1" colspan="1">−177.8 (5)</td><td rowspan="1" colspan="1">C13—C14—C15—C16</td><td rowspan="1" colspan="1">−1.2 (13)</td></tr><tr><td rowspan="1" colspan="1">N1—N2—C7—C8</td><td rowspan="1" colspan="1">−2.2 (10)</td><td rowspan="1" colspan="1">C14—C15—C16—C11</td><td rowspan="1" colspan="1">−2.0 (12)</td></tr><tr><td rowspan="1" colspan="1">N1—N2—C7—C12</td><td rowspan="1" colspan="1">177.6 (6)</td><td rowspan="1" colspan="1">C12—C11—C16—C15</td><td rowspan="1" colspan="1">3.8 (11)</td></tr><tr><td rowspan="1" colspan="1">Pd1—O1—C8—C7</td><td rowspan="1" colspan="1">1.8 (10)</td><td rowspan="1" colspan="1">C10—C11—C16—C15</td><td rowspan="1" colspan="1">−173.9 (7)</td></tr></table></table-wrap><p>Symmetry code: (i) −<italic>x</italic>+1, −<italic>y</italic>+1, −<italic>z</italic>+1.</p></sec><sec id="tablewraphbondslong"><title>Hydrogen-bond geometry (Å, º)</title><p>Cg2 is the centroid of ring C1-C6.</p><table-wrap position="anchor" id="d1e2138"><table rules="all" frame="box" style="table-layout:fixed" summary=""><colgroup span="5"><col span="1"></col><col span="1"></col><col span="1"></col><col span="1"></col><col span="1"></col></colgroup><tr><td rowspan="1" colspan="1"><italic>D</italic>—H···<italic>A</italic></td><td rowspan="1" colspan="1"><italic>D</italic>—H</td><td rowspan="1" colspan="1">H···<italic>A</italic></td><td rowspan="1" colspan="1"><italic>D</italic>···<italic>A</italic></td><td rowspan="1" colspan="1"><italic>D</italic>—H···<italic>A</italic></td></tr><tr><td rowspan="1" colspan="1">C10—H10···<italic>Cg</italic>2<sup>ii</sup></td><td rowspan="1" colspan="1">0.95</td><td rowspan="1" colspan="1">2.70</td><td rowspan="1" colspan="1">3.371 (8)</td><td rowspan="1" colspan="1">128</td></tr></table></table-wrap><p>Symmetry code: (ii) <italic>x</italic>+1/2, −<italic>y</italic>+3/2, <italic>z</italic>+1/2.</p></sec></app></app-group><ref-list><title>References</title><ref id="bb1"><mixed-citation publication-type="other">Alcock, N. 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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>Pour manipuler ce document sous Unix (Dilib)
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