{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,6]],"date-time":"2025-10-06T09:13:43Z","timestamp":1759742023935,"version":"3.37.3"},"reference-count":0,"publisher":"International Union of Crystallography (IUCr)","issue":"6","license":[{"start":{"date-parts":[[2019,5,15]],"date-time":"2019-05-15T00:00:00Z","timestamp":1557878400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2019,5,15]],"date-time":"2019-05-15T00:00:00Z","timestamp":1557878400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"accepted":{"date-parts":[[2019,4,23]]},"published-print":{"date-parts":[[2019,6,1]]},"abstract":"<jats:p>The structures of seven divalent metal cation compounds of Ponceau Xylidine {PX; systematic name of dication: 4-[2-(3,4-dimethylphenyl)hydrazin-1-ylidene]-3-oxo-3,4-dihydronaphthalene-2,7-disulfonate}, also known as Acid Red 26, CI 16150, and of five divalent metal cation compounds of Crystal Scarlet {CS; systematic name of dication: 8-[2-(naphthalen-1-yl)hydrazin-1-ylidene]-7-oxo-7,8-dihydronaphthalene-1,3-disulfonate}, also known as Acid Red 44, CI 16250, are presented. These are hexaaquamagnesium(II) PX dimethylformamide (DMF) monosolvate, [Mg(H<jats:sub>2<\/jats:sub>O)<jats:sub>6<\/jats:sub>](C<jats:sub>18<\/jats:sub>H<jats:sub>14<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>7<\/jats:sub>S<jats:sub>2<\/jats:sub>)\u00b7C<jats:sub>3<\/jats:sub>H<jats:sub>7<\/jats:sub>NO, (I); heptaaquacalcium(II) PX 2.5-hydrate, [Ca(H<jats:sub>2<\/jats:sub>O)<jats:sub>7<\/jats:sub>](C<jats:sub>18<\/jats:sub>H<jats:sub>14<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>7<\/jats:sub>S<jats:sub>2<\/jats:sub>)\u00b72.5H<jats:sub>2<\/jats:sub>O, (II); <jats:italic>catena<\/jats:italic>-poly[aqua(\u03bc-DMF)tris(DMF)bis(\u03bc<jats:sub>3<\/jats:sub>-PX)distrontium(II)], [Sr(C<jats:sub>18<\/jats:sub>H<jats:sub>14<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>7<\/jats:sub>S<jats:sub>2<\/jats:sub>)(C<jats:sub>3<\/jats:sub>H<jats:sub>7<\/jats:sub>NO)<jats:sub>2<\/jats:sub>(H<jats:sub>2<\/jats:sub>O)<jats:sub>0.5<\/jats:sub>]<jats:sub>\n                     <jats:italic>n<\/jats:italic>\n                  <\/jats:sub>, (III);  the transition-metal series hexaaquametal(II) PX DMF monosolvate, [<jats:italic>M<\/jats:italic>(H<jats:sub>2<\/jats:sub>O)<jats:sub>6<\/jats:sub>](C<jats:sub>18<\/jats:sub>H<jats:sub>14<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>7<\/jats:sub>S<jats:sub>2<\/jats:sub>)\u00b7C<jats:sub>3<\/jats:sub>H<jats:sub>7<\/jats:sub>NO, where <jats:italic>M<\/jats:italic> (metal) = Co, (IV), Ni, (V), Cu, (VI), and Zn, (VII); heptaaquacalcium(II) CS monohydrate, [Ca(H<jats:sub>2<\/jats:sub>O)<jats:sub>7<\/jats:sub>](C<jats:sub>20<\/jats:sub>H<jats:sub>13<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>7<\/jats:sub>S<jats:sub>2<\/jats:sub>)\u00b7H<jats:sub>2<\/jats:sub>O, (VIII); octaaquastrontium(II) CS monohydrate, [Sr(H<jats:sub>2<\/jats:sub>O)<jats:sub>8<\/jats:sub>](C<jats:sub>20<\/jats:sub>H<jats:sub>13<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>7<\/jats:sub>S<jats:sub>2<\/jats:sub>)\u00b7H<jats:sub>2<\/jats:sub>O, (IX); <jats:italic>catena<\/jats:italic>-poly[[triaqua(DMF)barium(II)]-\u03bc-CS], [Ba(C<jats:sub>20<\/jats:sub>H<jats:sub>13<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>7<\/jats:sub>S<jats:sub>2<\/jats:sub>)(C<jats:sub>3<\/jats:sub>H<jats:sub>7<\/jats:sub>NO)(H<jats:sub>2<\/jats:sub>O)<jats:sub>3<\/jats:sub>]<jats:sub>\n                     <jats:italic>n<\/jats:italic>\n                  <\/jats:sub>, (X); tetrakis(DMF)(CS)copper(II) monohydrate, [Cu(C<jats:sub>20<\/jats:sub>H<jats:sub>13<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>7<\/jats:sub>S<jats:sub>2<\/jats:sub>)(C<jats:sub>3<\/jats:sub>H<jats:sub>7<\/jats:sub>NO)<jats:sub>4<\/jats:sub>]\u00b7H<jats:sub>2<\/jats:sub>O, (XI); and <jats:italic>catena<\/jats:italic>-poly[[[aquatris(DMF)zinc(III)]-\u03bc-CS] diethyl ether hemisolvate], {[Zn(C<jats:sub>20<\/jats:sub>H<jats:sub>13<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>7<\/jats:sub>S<jats:sub>2<\/jats:sub>)(C<jats:sub>3<\/jats:sub>H<jats:sub>7<\/jats:sub>NO)<jats:sub>3<\/jats:sub>(H<jats:sub>2<\/jats:sub>O)]\u00b70.5C<jats:sub>4<\/jats:sub>H<jats:sub>10<\/jats:sub>O}<jats:sub>\n                     <jats:italic>n<\/jats:italic>\n                  <\/jats:sub>, (XII). In all cases, the structures obtained were solvates with dimethylformamide (DMF) and\/or water present. The disulfonated naphthalene-based azo anions adopt hydrazone tautomeric forms. The structures of the Mg salt and of four transition-metal forms (<jats:italic>M<\/jats:italic> = Co, Ni, Cu and Zn) of PX are found to form an isostructural series. All have solvent-separated ion-pair (SSIP) type structures and the formula [<jats:italic>M<\/jats:italic>(H<jats:sub>2<\/jats:sub>O)<jats:sub>6<\/jats:sub>][PX]\u00b7DMF. The Ca salt of PX also has an SSIP structure, but has a higher hydration state, [Ca(H<jats:sub>2<\/jats:sub>O)<jats:sub>7<\/jats:sub>][PX]\u00b72.5H<jats:sub>2<\/jats:sub>O. In contrast, the Sr salt of PX, [Sr(PX)(DMF)<jats:sub>2<\/jats:sub>(H<jats:sub>2<\/jats:sub>O)<jats:sub>0.5<\/jats:sub>]<jats:sub>\n                     <jats:italic>n<\/jats:italic>\n                  <\/jats:sub> forms a one-dimensional coordination polymer. Both the Ca and the Sr salt of CS have an SSIP structure, namely [Ca(H<jats:sub>2<\/jats:sub>O)<jats:sub>7<\/jats:sub>][CS]\u00b7H<jats:sub>2<\/jats:sub>O and [Sr(H<jats:sub>2<\/jats:sub>O)<jats:sub>8<\/jats:sub>][CS]\u00b7H<jats:sub>2<\/jats:sub>O, whilst the heavier Ba analogue, [Ba(CS)(DMF)(H<jats:sub>2<\/jats:sub>O)<jats:sub>3<\/jats:sub>]<jats:sub>\n                     <jats:italic>n<\/jats:italic>\n                  <\/jats:sub>, forms a one-dimensional coordination polymer. Unlike PX, two CS structures containing transition metals are found to be coordination complexes, [Cu(CS)(DMF)<jats:sub>4<\/jats:sub>]\u00b7H<jats:sub>2<\/jats:sub>O and {[Zn(CS)(DMF)<jats:sub>3<\/jats:sub>(H<jats:sub>2<\/jats:sub>O)]\u00b70.5Et<jats:sub>2<\/jats:sub>O}<jats:sub>\n                     <jats:italic>n<\/jats:italic>\n                  <\/jats:sub>. This suggests that CS is a better ligand than PX for transition metals. The Cu complex forms discrete molecules with Cu in a square-pyramidal environment, whilst the Zn species is a one-dimensional coordination polymer based on octahedral Zn centres.<\/jats:p>","DOI":"10.1107\/s2053229619005540","type":"journal-article","created":{"date-parts":[[2019,5,15]],"date-time":"2019-05-15T12:44:05Z","timestamp":1557924245000},"page":"633-642","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":5,"title":["Disulfonated azo dyes: metal coordination and ion-pair separation in twelve <i>M<\/i>\n                  <sup>II<\/sup> compounds of Ponceau Xylidine and Crystal Scarlet"],"prefix":"10.1107","volume":"75","author":[{"given":"David T.","family":"Black","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2319-3725","authenticated-orcid":true,"given":"Alan R.","family":"Kennedy","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kiara M.","family":"Lobato","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2019,5,15]]},"container-title":["Acta Crystallographica Section C Structural 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