{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T11:36:36Z","timestamp":1785411396791,"version":"3.56.0"},"reference-count":33,"publisher":"International Union of Crystallography (IUCr)","issue":"5","license":[{"start":{"date-parts":[[2025,4,8]],"date-time":"2025-04-08T00:00:00Z","timestamp":1744070400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2025,4,8]],"date-time":"2025-04-08T00:00:00Z","timestamp":1744070400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"funder":[{"name":"University of the National Education Commission","award":["BN.711-56\/PBU\/2021"],"award-info":[{"award-number":["BN.711-56\/PBU\/2021"]}]}],"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":[[2025,3,21]]},"published-print":{"date-parts":[[2025,5,1]]},"abstract":"<jats:p>\n                    A number of piperazine derivatives of hydantoin display high affinity for \u03b1\n                    <jats:sub>1<\/jats:sub>\n                    -adrenoreceptors and antagonistic properties, which make them potent hypotensive agents. In order to study the correlations between affinity for \u03b1\n                    <jats:sub>1<\/jats:sub>\n                    -adrenoreceptors and molecular structures, the crystal structures of six piperazine derivatives of 5,5-dimethylhydantoin were determined by X-ray diffraction, namely, 4-(3-{3-[(2,4-dichlorophenyl)methyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hydroxypropyl)-1-phenylpiperazine-1,4-diium dichloride monohydrate ethyl acetate hemisolvate, C\n                    <jats:sub>25<\/jats:sub>\n                    H\n                    <jats:sub>32<\/jats:sub>\n                    Cl\n                    <jats:sub>2<\/jats:sub>\n                    N\n                    <jats:sub>4<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    <jats:sup>2+<\/jats:sup>\n                    \u00b72Cl\n                    <jats:sup>\u2212<\/jats:sup>\n                    \u00b7H\n                    <jats:sub>2<\/jats:sub>\n                    O\u00b70.5C\n                    <jats:sub>4<\/jats:sub>\n                    H\n                    <jats:sub>8<\/jats:sub>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    (\n                    <jats:bold>1<\/jats:bold>\n                    ), 4-(2-cyanophenyl)-1-(3-{3-[(2,4-dichlorophenyl)methyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hydroxypropyl)piperazin-1-ium chloride acetonitrile monosolvate, C\n                    <jats:sub>26<\/jats:sub>\n                    H\n                    <jats:sub>30<\/jats:sub>\n                    Cl\n                    <jats:sub>2<\/jats:sub>\n                    N\n                    <jats:sub>5<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7Cl\n                    <jats:sup>\u2212<\/jats:sup>\n                    \u00b7C\n                    <jats:sub>2<\/jats:sub>\n                    H\n                    <jats:sub>3<\/jats:sub>\n                    N (\n                    <jats:bold>2<\/jats:bold>\n                    ), 1-(3-{3-[(2,4-dichlorophenyl)methyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hydroxypropyl)-4-(3,4-dimethylphenyl)piperazin-1-ium chloride, C\n                    <jats:sub>27<\/jats:sub>\n                    H\n                    <jats:sub>35<\/jats:sub>\n                    Cl\n                    <jats:sub>2<\/jats:sub>\n                    N\n                    <jats:sub>4<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7Cl\n                    <jats:sup>\u2212<\/jats:sup>\n                    (\n                    <jats:bold>3<\/jats:bold>\n                    ), 1-(3-{3-[(2,4-dichlorophenyl)methyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hydroxypropyl)-4-(3-methoxyphenyl)piperazin-1-ium chloride, C\n                    <jats:sub>26<\/jats:sub>\n                    H\n                    <jats:sub>33<\/jats:sub>\n                    Cl\n                    <jats:sub>2<\/jats:sub>\n                    N\n                    <jats:sub>4<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7Cl\n                    <jats:sup>\u2212<\/jats:sup>\n                    (\n                    <jats:bold>4<\/jats:bold>\n                    ), 4-(2,3-dichlorophenyl)-1-(3-{3-[(2,4-dichlorophenyl)methyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl}-2-hydroxypropyl)piperazin-1-ium chloride 0.2-hydrate, C\n                    <jats:sub>25<\/jats:sub>\n                    H\n                    <jats:sub>29<\/jats:sub>\n                    Cl\n                    <jats:sub>4<\/jats:sub>\n                    N\n                    <jats:sub>4<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    <jats:sup>+<\/jats:sup>\n                    \u00b7Cl\n                    <jats:sup>\u2212<\/jats:sup>\n                    \u00b70.2H\n                    <jats:sub>2<\/jats:sub>\n                    O (\n                    <jats:bold>5<\/jats:bold>\n                    ), and 3-[(2,4-dichlorophenyl)methyl]-1-{3-[4-(3,4-dichlorophenyl)piperazin-1-yl]-2-hydroxypropyl}-5,5-dimethylimidazolidine-2,4-dione, C\n                    <jats:sub>25<\/jats:sub>\n                    H\n                    <jats:sub>28<\/jats:sub>\n                    Cl\n                    <jats:sub>4<\/jats:sub>\n                    N\n                    <jats:sub>4<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    (\n                    <jats:bold>6<\/jats:bold>\n                    ). The compounds crystallize in the centrosymmetric triclinic space group, except for\n                    <jats:bold>2<\/jats:bold>\n                    , which crystallizes in the monoclinic space group\n                    <jats:italic>P<\/jats:italic>\n                    2\n                    <jats:sub>1<\/jats:sub>\n                    \/\n                    <jats:italic>c<\/jats:italic>\n                    . For all six compounds, one molecule is observed in the asymmetric unit. The molecule of\n                    <jats:bold>1<\/jats:bold>\n                    is doubly protonated at both N atoms of the piperazine ring, whereas\n                    <jats:bold>2<\/jats:bold>\n                    ,\n                    <jats:bold>3<\/jats:bold>\n                    ,\n                    <jats:bold>4<\/jats:bold>\n                    and\n                    <jats:bold>5<\/jats:bold>\n                    are only protonated at one ring N atom. The protonated N atoms are engaged in charge-assisted hydrogen bonds with the chloride anions, and in\n                    <jats:bold>1<\/jats:bold>\n                    the N atom interacts with the chloride anion\n                    <jats:italic>via<\/jats:italic>\n                    the water molecule. The crystal packing in the protonated molecules (\n                    <jats:bold>1<\/jats:bold>\n                    \u2013\n                    <jats:bold>5<\/jats:bold>\n                    ) is in each case dominated by a network of N\u2014H\n                    <jats:sup>+<\/jats:sup>\n                    ...Cl\n                    <jats:sup>\u2212<\/jats:sup>\n                    , O\u2014H...Cl\n                    <jats:sup>\u2212<\/jats:sup>\n                    and C\u2014H...Cl\n                    <jats:sup>\u2212<\/jats:sup>\n                    hydrogen bonds, while in the base molecule of\n                    <jats:bold>6<\/jats:bold>\n                    , O\u2014H...O hydrogen bonds dominate.\n                  <\/jats:p>","DOI":"10.1107\/s2053229625002608","type":"journal-article","created":{"date-parts":[[2025,3,31]],"date-time":"2025-03-31T06:26:05Z","timestamp":1743402365000},"page":"264-272","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystallographic studies of piperazine derivatives of 5,5-dimethylhydantoin in the search for structural features of \u03b1\n                    <sub>1<\/sub>\n                    -adrenoreceptors antagonists"],"prefix":"10.1107","volume":"81","author":[{"given":"Ewa","family":"\u017bes\u0142awska","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0276-9003","authenticated-orcid":true,"given":"Wojciech","family":"Nitek","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03bqmcz70","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jadwiga","family":"Handzlik","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03bqmcz70","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2025,4,8]]},"reference":[{"key":"eq3022_bb1","doi-asserted-by":"crossref","first-page":"2118","DOI":"10.1021\/jm010821u","volume":"44","author":"Barbaro","year":"2001","journal-title":"J. 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