{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T12:41:38Z","timestamp":1790685698870,"version":"4.1.0"},"reference-count":42,"publisher":"International Union of Crystallography (IUCr)","issue":"9","license":[{"start":{"date-parts":[[2019,8,16]],"date-time":"2019-08-16T00:00:00Z","timestamp":1565913600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2019,8,16]],"date-time":"2019-08-16T00:00:00Z","timestamp":1565913600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["MRI CHE1625732"],"award-info":[{"award-number":["MRI CHE1625732"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"accepted":{"date-parts":[[2019,8,8]]},"published-print":{"date-parts":[[2019,9,1]]},"abstract":"<jats:p>Imidazolium salts are common building blocks for functional materials and in the synthesis of N-heterocyclic carbene (NHC) as \u03c3-donor ligands for stable metal complexes. The title salt, 1,3-bis(4-hydroxyphenyl)-1<jats:italic>H<\/jats:italic>-imidazol-3-ium chloride (IOH\u00b7Cl), C<jats:sub>15<\/jats:sub>H<jats:sub>13<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub><jats:sup>+<\/jats:sup>\u00b7Cl<jats:sup>\u2212<\/jats:sup>, is a new imidazolium salt with a hydroxy functionality. The synthesis of IOH\u00b7Cl was achieved in high yield<jats:italic>via<\/jats:italic>a two-step procedure involving a diazabutadiene precursor followed by ring closure using trimethylchlorosilane and paraformaldehyde. The structure of IOH\u00b7Cl consists of a central planar imidazolium ring (r.m.s. deviation = 0.0015\u2005\u00c5), with out-of-plane phenolic side arms. The dihedral angles between the 4-hydroxyphenyl substituents and the imidazole ring are 55.27\u2005(7) and 48.85\u2005(11)\u00b0. In the crystal, O\u2014H...Cl hydrogen bonds connect the distal hydroxy groups and Cl<jats:sup>\u2212<\/jats:sup>anions in adjacent asymmetric units, one related by inversion (\u2212<jats:italic>x<\/jats:italic>\u00a0+\u00a01, \u2212<jats:italic>y<\/jats:italic>\u00a0+\u00a01, \u2212<jats:italic>z<\/jats:italic>\u00a0+\u00a01) and one by the<jats:italic>n<\/jats:italic>-glide (<jats:italic>x<\/jats:italic>\u00a0\u2212\u00a0{1\\over 2}, \u2212<jats:italic>y<\/jats:italic>\u00a0+\u00a0{1\\over 2},<jats:italic>z<\/jats:italic>\u00a0\u2212\u00a0{1\\over 2}), with donor\u2013acceptor distances of 2.977\u2005(2) and 3.0130\u2005(18)\u2005\u00c5, respectively. The phenolic rings are each \u03c0\u2013\u03c0 stacked with their respective inversion-related [(\u2212<jats:italic>x<\/jats:italic>\u00a0+\u00a01, \u2212<jats:italic>y<\/jats:italic>\u00a0+\u00a01, \u2212<jats:italic>z<\/jats:italic>\u00a0+\u00a01) and (\u2212<jats:italic>x<\/jats:italic>, \u2212<jats:italic>y<\/jats:italic>\u00a0+\u00a01, \u2212<jats:italic>z<\/jats:italic>\u00a0+\u00a01)] counterparts, with interplanar distances of 3.560\u2005(3) and 3.778\u2005(3)\u2005\u00c5. The only other noteworthy intermolecular interaction is an O...O (not hydrogen bonded) close contact of 2.999\u2005(3)\u2005\u00c5 between crystallographically different hydroxy O atoms on translationally adjacent molecules (<jats:italic>x<\/jats:italic>\u00a0+\u00a01,<jats:italic>y<\/jats:italic>,<jats:italic>x<\/jats:italic>\u00a0+\u00a01).<\/jats:p>","DOI":"10.1107\/s2056989019011058","type":"journal-article","created":{"date-parts":[[2019,8,15]],"date-time":"2019-08-15T15:01:54Z","timestamp":1565881314000},"page":"1311-1315","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis and crystal structure of 1,3-bis(4-hydroxyphenyl)-1<i>H<\/i>-imidazol-3-ium chloride"],"prefix":"10.1107","volume":"75","author":[{"given":"R. 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