{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T14:13:01Z","timestamp":1785420781952,"version":"3.56.0"},"reference-count":22,"publisher":"International Union of Crystallography (IUCr)","issue":"4","license":[{"start":{"date-parts":[[2026,3,5]],"date-time":"2026-03-05T00:00:00Z","timestamp":1772668800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2026,3,5]],"date-time":"2026-03-05T00:00:00Z","timestamp":1772668800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/100007472","name":"University of Kentucky","doi-asserted-by":"crossref","id":[{"id":"10.13039\/100007472","id-type":"DOI","asserted-by":"crossref"}]}],"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":[[2026,2,27]]},"published-print":{"date-parts":[[2026,4,1]]},"abstract":"<jats:p>\n                    Etoxazole (C\n                    <jats:sub>21<\/jats:sub>\n                    H\n                    <jats:sub>23<\/jats:sub>\n                    F\n                    <jats:sub>2<\/jats:sub>\n                    NO\n                    <jats:sub>2<\/jats:sub>\n                    ) is a fluorinated insecticide\/acaricide that acts as an inhibitor of chitin biosynthesis. Its degradation products include several persistent environmental contaminants, including a metabolite designated \u2018R7\u2019 (C\n                    <jats:sub>19<\/jats:sub>\n                    H\n                    <jats:sub>25<\/jats:sub>\n                    F\n                    <jats:sub>2<\/jats:sub>\n                    NO\n                    <jats:sub>3<\/jats:sub>\n                    ), which has a readily protonated amine group, to give the R7H\n                    <jats:sup>+<\/jats:sup>\n                    cation, namely, 2-azaniumyl-2-(4-\n                    <jats:italic>tert<\/jats:italic>\n                    -butyl-2-ethoxyphenyl)ethyl 2,6-difluorobenzoate. This paper reports the crystal structures of two salts of R7H\n                    <jats:sup>+<\/jats:sup>\n                    : the bromide (\n                    <jats:bold>I<\/jats:bold>\n                    : C\n                    <jats:sub>21<\/jats:sub>\n                    H\n                    <jats:sub>26<\/jats:sub>\n                    F\n                    <jats:sub>2<\/jats:sub>\n                    NO\n                    <jats:sub>3<\/jats:sub>\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7Br\n                    <jats:sup>\u2212<\/jats:sup>\n                    ) and the 3-carboxyprop-2-enoate (hereafter fumarate) (\n                    <jats:bold>II<\/jats:bold>\n                    : C\n                    <jats:sub>21<\/jats:sub>\n                    H\n                    <jats:sub>26<\/jats:sub>\n                    F\n                    <jats:sub>2<\/jats:sub>\n                    NO\n                    <jats:sub>3<\/jats:sub>\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7C\n                    <jats:sub>4<\/jats:sub>\n                    H\n                    <jats:sub>3<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    <jats:sup>\u2212<\/jats:sup>\n                    ). Although the R7H\n                    <jats:sup>+<\/jats:sup>\n                    cations in\n                    <jats:bold>I<\/jats:bold>\n                    and\n                    <jats:bold>II<\/jats:bold>\n                    are chemically identical, the salts crystallize in substantially different structures. Crystals of\n                    <jats:bold>I<\/jats:bold>\n                    are tetragonal, space-group type\n                    <jats:italic>P<\/jats:italic>\n                    <jats:overline>4<\/jats:overline>\n                    2\n                    <jats:sub>1<\/jats:sub>\n                    <jats:italic>c<\/jats:italic>\n                    , whereas those of\n                    <jats:bold>II<\/jats:bold>\n                    are monoclinic, space-group type\n                    <jats:italic>P<\/jats:italic>\n                    2\n                    <jats:sub>1<\/jats:sub>\n                    \/\n                    <jats:italic>n<\/jats:italic>\n                    , each containing one cation\u2013anion pair in their respective asymmetric units (\n                    <jats:italic>Z<\/jats:italic>\n                    \u2032 = 1). The R7H\n                    <jats:sup>+<\/jats:sup>\n                    cation in both structures feature a central 2-azaniumyl linker connecting 4-\n                    <jats:italic>tert<\/jats:italic>\n                    -butyl-2-ethoxyphenyl and 2,6-difluorobenzoate rings. Cation conformation is primarily governed by different torsional degrees of freedom, leading to distinct overall conformations. The crystal packing in\n                    <jats:bold>I<\/jats:bold>\n                    is driven by N\u2014H...Br hydrogen bonds, \u03c0\u2013\u03c0 and C\u2014H...\u03c0 interactions, which arrange the cations into columns parallel to the crystallographic\n                    <jats:italic>c<\/jats:italic>\n                    -axis. In contrast, the packing in\n                    <jats:bold>II<\/jats:bold>\n                    consists of N\u2014H...O hydrogen bonds to adjacent fumarate anions, forming extended hydrogen-bonded chains. The fumarate anions are sandwiched between R7H\n                    <jats:sup>+<\/jats:sup>\n                    cations, placing the fumarate double bond between aromatic rings. Hirshfeld-surface analysis shows that intermolecular contacts in both structures are dominated by interactions involving hydrogen (93.4% in\n                    <jats:bold>I<\/jats:bold>\n                    , 92.2% in\n                    <jats:bold>II<\/jats:bold>\n                    ).\n                  <\/jats:p>","DOI":"10.1107\/s2056989026002197","type":"journal-article","created":{"date-parts":[[2026,2,27]],"date-time":"2026-02-27T16:56:51Z","timestamp":1772211411000},"page":"326-330","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Crystal structures and Hirshfeld surface comparison of fumarate and bromide salts of the etoxazole metabolite designated R7 (aminium ions)"],"prefix":"10.1107","volume":"82","author":[{"given":"Thaluru M.","family":"Mohan Kumar","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03am10p12","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chaluvarangaiah","family":"Sowbhagya","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03am10p12","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Papegowda","family":"Bhavya","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hemmige S.","family":"Yathirajan","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/012bxv356","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5777-3918","authenticated-orcid":true,"given":"Sean","family":"Parkin","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02k3smh20","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2026,3,5]]},"reference":[{"key":"nx2032_bb1","unstructured":"Bruker (2023). 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