{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T14:14:16Z","timestamp":1785420856401,"version":"3.56.0"},"reference-count":40,"publisher":"International Union of Crystallography (IUCr)","issue":"11","license":[{"start":{"date-parts":[[2025,10,20]],"date-time":"2025-10-20T00:00:00Z","timestamp":1760918400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2025,10,20]],"date-time":"2025-10-20T00:00:00Z","timestamp":1760918400000},"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":["DNa.711.42.2025.PBU"],"award-info":[{"award-number":["DNa.711.42.2025.PBU"]}]},{"DOI":"10.13039\/501100000780","name":"European Union","doi-asserted-by":"crossref","award":["POIR.04.02.00-00-D001\/20"],"award-info":[{"award-number":["POIR.04.02.00-00-D001\/20"]}],"id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"crossref"}]}],"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":[[2025,10,7]]},"published-print":{"date-parts":[[2025,11,1]]},"abstract":"\n Four new crystal structures of the salts of\n N<\/jats:italic>\n -[(2,3-dimethylphenoxy)alkyl]aminoalkanol derivatives with anticonvulsant activity are reported. Bis{D,L-\n trans<\/jats:italic>\n -\n N<\/jats:italic>\n -[(2,3-dimethylphenoxy)ethyl]-1-hydroxycyclohexan-2-aminium} succinate, 2C\n 16<\/jats:sub>\n H\n 26<\/jats:sub>\n NO\n 2<\/jats:sub>\n +<\/jats:sup>\n \u00b7C\n 4<\/jats:sub>\n H\n 4<\/jats:sub>\n O\n 4<\/jats:sub>\n 2\u2212<\/jats:sup>\n ,\n 1<\/jats:bold>\n , and its polymorph\n 1p<\/jats:bold>\n , crystallize in the monoclinic space group\n P<\/jats:italic>\n 2\n 1<\/jats:sub>\n \/\n n<\/jats:italic>\n ,\n 1<\/jats:bold>\n with two cations and one anion, and\n 1p<\/jats:bold>\n with four cations and two anions in the asymmetric unit. The other two salts, D,L-\n trans<\/jats:italic>\n -\n N<\/jats:italic>\n -[(2,3-dimethylphenoxy)ethyl]-1-hydroxycyclohexan-2-aminium 6-carboxypyridine-2-carboxylate, C\n 16<\/jats:sub>\n H\n 25<\/jats:sub>\n NO\n 2<\/jats:sub>\n +<\/jats:sup>\n \u00b7C\n 7<\/jats:sub>\n H\n 4<\/jats:sub>\n O\n 4<\/jats:sub>\n \u2212<\/jats:sup>\n ,\n 2<\/jats:bold>\n , and\n N<\/jats:italic>\n -[(2,3-dimethylphenoxy)propyl]-3-hydroxypiperidinium pyridine-2-carboxylate, C\n 16<\/jats:sub>\n H\n 26<\/jats:sub>\n NO\n 2<\/jats:sub>\n +<\/jats:sup>\n \u00b7C\n 6<\/jats:sub>\n H\n 4<\/jats:sub>\n O\n 2<\/jats:sub>\n \u2212<\/jats:sup>\n ,\n 3<\/jats:bold>\n , crystallize in the monoclinic space group\n P<\/jats:italic>\n 2\n 1<\/jats:sub>\n \/\n c<\/jats:italic>\n , with one cation and one anion in each asymmetric unit. The geometry of the created polymorphs indicates the main differences in the conformation of the linker between the two rings. The arrangement of the ether O atom and the N atom shows an unusual antiperiplanar conformation for the cations of\n 1p<\/jats:bold>\n . The crystal packing of all four salts is dominated by charge-assisted hydrogen bonding between the protonated N atom and the carboxylate group of the corresponding acid. Structural studies have been enriched by quantum chemical calculations.\n <\/jats:p>","DOI":"10.1107\/s2053229625008745","type":"journal-article","created":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T12:14:16Z","timestamp":1760271256000},"page":"639-647","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Conformational analysis of the salts of\n N<\/i>\n -[(2,3-dimethylphenoxy)alkyl]aminoalkanol derivatives"],"prefix":"10.1107","volume":"81","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0276-9003","authenticated-orcid":true,"given":"Wojciech","family":"Nitek","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03bqmcz70","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6042-2510","authenticated-orcid":true,"given":"Krzysztof","family":"Zborowski","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03bqmcz70","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Agnieszka","family":"Kania","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Henryk","family":"Marona","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03bqmcz70","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anna M.","family":"Waszkielewicz","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03bqmcz70","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ewa","family":"\u017bes\u0142awska","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2025,10,20]]},"reference":[{"key":"wv3021_bb1","doi-asserted-by":"crossref","first-page":"o932","DOI":"10.1107\/S1600536811009287","volume":"67","author":"Aghabozorg","year":"2011","journal-title":"Acta Cryst. E"},{"key":"wv3021_bb2","first-page":"231","volume":"8","author":"Alexander","year":"1986","journal-title":"Neurobehav. Toxicol. Teratol."},{"key":"wv3021_bb3","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"wv3021_bb4","doi-asserted-by":"crossref","first-page":"1555","DOI":"10.1002\/anie.199515551","volume":"34","author":"Bernstein","year":"1995","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"wv3021_bb5","doi-asserted-by":"crossref","first-page":"545","DOI":"10.1016\/j.pharep.2014.03.009","volume":"66","author":"Borowicz","year":"2014","journal-title":"Pharmacol. Rep."},{"key":"wv3021_bb6","doi-asserted-by":"crossref","first-page":"306","DOI":"10.1107\/S1600576715001132","volume":"48","author":"Burla","year":"2015","journal-title":"J. Appl. Cryst."},{"key":"wv3021_bb7","doi-asserted-by":"crossref","first-page":"161","DOI":"10.2165\/00003495-197917030-00003","volume":"17","author":"Chew","year":"1979","journal-title":"Drugs"},{"key":"wv3021_bb8","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/0009-2614(96)00349-1","volume":"255","author":"Cossi","year":"1996","journal-title":"Chem. Phys. Lett."},{"key":"wv3021_bb9","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"wv3021_bb10","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1053\/seiz.2001.0644","volume":"11","author":"Fischer","year":"2002","journal-title":"Seizure"},{"key":"wv3021_bb11","doi-asserted-by":"crossref","first-page":"3654","DOI":"10.1063\/1.444267","volume":"77","author":"Francl","year":"1982","journal-title":"J. Chem. Phys."},{"key":"wv3021_bb12","unstructured":"Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A. Jr, Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, R. L., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, O., Foresman, J. B., Ortiz, J. V., Cioslowski, J. & Fox, D. J. (2013). GAUSSIAN09. Revision D.01. Gaussian Inc., Wallingford, CT, USA. https:\/\/gaussian.com\/."},{"key":"wv3021_bb13","doi-asserted-by":"crossref","first-page":"o2151","DOI":"10.1107\/S1600536809031493","volume":"65","author":"Kim","year":"2009","journal-title":"Acta Cryst. E"},{"key":"wv3021_bb14","doi-asserted-by":"crossref","unstructured":"Koch, W. & Holthausen, M. C. A. (2000). In Chemist's guide to density functional theory. Weinheim: Wiley-VCH Verlag GmbH.","DOI":"10.1002\/3527600043"},{"key":"wv3021_bb15","doi-asserted-by":"crossref","first-page":"14","DOI":"10.1212\/CPJ.0b013e31823d07d1","volume":"1","author":"Krauss","year":"2011","journal-title":"Neur. Clin. Pract."},{"key":"wv3021_bb16","doi-asserted-by":"crossref","first-page":"606","DOI":"10.1124\/pr.120.019539","volume":"72","author":"L\u00f6scher","year":"2020","journal-title":"Pharmacol. Rev."},{"key":"wv3021_bb17","doi-asserted-by":"crossref","first-page":"5639","DOI":"10.1063\/1.438980","volume":"72","author":"McLean","year":"1980","journal-title":"J. Chem. Phys."},{"key":"wv3021_bb18","unstructured":"Murray, J. S. (1996). In Molecular electrostatic potentials: concepts and applications. Amsterdam: Elsevier Science BV."},{"key":"wv3021_bb19","doi-asserted-by":"crossref","first-page":"681","DOI":"10.1107\/S2053229620008244","volume":"76","author":"Nitek","year":"2020","journal-title":"Acta Cryst. C"},{"key":"wv3021_bb20","doi-asserted-by":"crossref","first-page":"14","DOI":"10.1107\/S2053229621012614","volume":"78","author":"Nitek","year":"2022","journal-title":"Acta Cryst. C"},{"key":"wv3021_bb21","doi-asserted-by":"crossref","first-page":"9381","DOI":"10.1002\/slct.201902648","volume":"4","author":"Pa\u0144czyk","year":"2019","journal-title":"ChemistrySelect"},{"key":"wv3021_bb22","doi-asserted-by":"crossref","first-page":"1933","DOI":"10.1039\/C8MD00430G","volume":"9","author":"Pa\u0144czyk","year":"2018","journal-title":"MedChemComm"},{"key":"wv3021_bb23","doi-asserted-by":"crossref","first-page":"329","DOI":"10.1107\/S2053229619002262","volume":"75","author":"Powers","year":"2019","journal-title":"Acta Cryst. C"},{"key":"wv3021_bb24","unstructured":"Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, Oxfordshire, England."},{"key":"wv3021_bb25","unstructured":"Rigaku OD (2023). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, Oxfordshire, England."},{"key":"wv3021_bb26","doi-asserted-by":"crossref","first-page":"116476","DOI":"10.1016\/j.ejmech.2024.116476","volume":"272","author":"S\u00e1nchez","year":"2024","journal-title":"Eur. J. Med. Chem."},{"key":"wv3021_bb27","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"wv3021_bb28","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"wv3021_bb29","doi-asserted-by":"crossref","first-page":"3513","DOI":"10.1039\/D2MA00075J","volume":"3","author":"Singh","year":"2022","journal-title":"Mater. Adv."},{"key":"wv3021_bb30","doi-asserted-by":"crossref","first-page":"135217","DOI":"10.1016\/j.molstruc.2023.135217","volume":"1283","author":"Suku","year":"2023","journal-title":"J. Mol. Struct."},{"key":"wv3021_bb31","doi-asserted-by":"crossref","first-page":"301","DOI":"10.3389\/fneur.2017.00301","volume":"8","author":"Tang","year":"2017","journal-title":"Front. Neurol."},{"key":"wv3021_bb32","doi-asserted-by":"crossref","first-page":"2999","DOI":"10.1021\/cr9904009","volume":"105","author":"Tomasi","year":"2005","journal-title":"Chem. Rev."},{"key":"wv3021_bb33","doi-asserted-by":"crossref","first-page":"2090","DOI":"10.3390\/ph3072090","volume":"3","author":"Wahab","year":"2010","journal-title":"Pharmaceuticals"},{"key":"wv3021_bb34","doi-asserted-by":"crossref","first-page":"4197","DOI":"10.1016\/j.bmc.2015.06.045","volume":"23","author":"Waszkielewicz","year":"2015","journal-title":"Bioorg. Med. Chem."},{"key":"wv3021_bb35","doi-asserted-by":"crossref","first-page":"1793","DOI":"10.1016\/j.bmc.2016.03.006","volume":"24","author":"Waszkielewicz","year":"2016","journal-title":"Bioorg. Med. Chem."},{"key":"wv3021_bb36","doi-asserted-by":"crossref","first-page":"35","DOI":"10.2174\/157018013804142500","volume":"10","author":"Waszkielewicz","year":"2013","journal-title":"Lett Drug Des Discov."},{"key":"wv3021_bb37","unstructured":"WHO. (2019). Epilepsy: a public health imperative. Summary. Geneva: World Health Organization. https:\/\/www.who.int\/publications\/i\/item\/epilepsy-a-public-health-imperative."},{"key":"wv3021_bb38","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1107\/S2053229619015948","volume":"76","author":"\u017bes\u0142awska","year":"2020","journal-title":"Acta Cryst. C"},{"key":"wv3021_bb39","doi-asserted-by":"crossref","first-page":"1151","DOI":"10.1107\/S2053229617016461","volume":"73","author":"\u017bes\u0142awska","year":"2017","journal-title":"Acta Cryst. C"},{"key":"wv3021_bb40","doi-asserted-by":"crossref","first-page":"856","DOI":"10.1107\/S2053229618008574","volume":"74","author":"\u017bes\u0142awska","year":"2018","journal-title":"Acta Cryst. C"}],"container-title":["Acta Crystallographica Section C Structural Chemistry"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/c\/issues\/2025\/11\/00\/wv3021\/wv3021.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/c\/issues\/2025\/11\/00\/wv3021\/wv3021.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,11,5]],"date-time":"2025-11-05T09:47:09Z","timestamp":1762336029000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2053229625008745"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,10,20]]},"references-count":40,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2025,11]]}},"alternative-id":["S2053229625008745"],"URL":"https:\/\/doi.org\/10.1107\/s2053229625008745","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2053229625008745\/wv3021sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2053229625008745\/wv30211sup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2053229625008745\/wv30211psup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2053229625008745\/wv30212sup4.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2053229625008745\/wv30213sup5.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2053229625008745\/wv30211sup6.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2053229625008745\/wv30211psup7.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2053229625008745\/wv30212sup8.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2053229625008745\/wv30213sup9.cml","asserted-by":"subject"}]},"ISSN":["2053-2296"],"issn-type":[{"value":"2053-2296","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,10,20]]},"assertion":[{"value":"Acta Crystallographica Section C: Structural Chemistry","order":0,"name":"journal","label":"Publication","explanation":{"URL":"https:\/\/journals.iucr.org\/c"},"group":{"name":"general","label":"General"}},{"value":"research papers","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/c\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?wv3021","order":2,"name":"article_metrics","label":"Article metrics","group":{"name":"general","label":"General"}},{"value":"Yes","order":0,"name":"peer_reviewed","label":"Peer reviewed","group":{"name":"peer_review","label":"Peer review"}},{"value":"Single blind","order":1,"name":"review_process","label":"Review process","group":{"name":"peer_review","label":"Peer review"}},{"value":"10 September 2025","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"7 October 2025","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"20 October 2025","order":2,"name":"published_online","label":"Published online","group":{"name":"publication_history","label":"Publication history"}},{"value":"This article has supporting information","name":"supplementary_materials","label":"Supplementary materials","explanation":{"URL":"https:\/\/scripts.iucr.org\/cgi-bin\/sendsup?wv3021"}},{"value":"\u00a9 Nitek\n et al.","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licensing","label":"Copyright and licencing"}},{"value":"IUCr licence to publish","order":1,"name":"license","label":"Licence","explanation":{"URL":"https:\/\/journals.iucr.org\/copyright\/licencetopublish.html"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}}]}}