{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,17]],"date-time":"2026-02-17T05:39:47Z","timestamp":1771306787136,"version":"3.50.1"},"reference-count":67,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2025,9,15]],"date-time":"2025-09-15T00:00:00Z","timestamp":1757894400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100012190","name":"Ministry of Science and Higher Education, Russia","doi-asserted-by":"publisher","award":["075\u201000365\u201025\u221200"],"award-info":[{"award-number":["075\u201000365\u201025\u221200"]}],"id":[{"id":"10.13039\/501100012190","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100012190","name":"Ministry of Science and Higher Education, Russia","doi-asserted-by":"publisher","award":["FSER\u20102024\u22120003"],"award-info":[{"award-number":["FSER\u20102024\u22120003"]}],"id":[{"id":"10.13039\/501100012190","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemPlusChem"],"published-print":{"date-parts":[[2025,11,10]]},"abstract":"<jats:p>\n                    New H\u2010bonded supramolecular assembliesare obtained using the polyfluorobiphenyl H\u2010donor derivatives and 18\u2010crown\u20106 ether. Cocrystals of octafluorobenzidine with 18\u2010crown\u20106 of 1:1 stoichiometry belong to the enantiomorphous space groups\n                    <jats:italic>P<\/jats:italic>\n                    6\n                    <jats:sub>5<\/jats:sub>\n                    and\n                    <jats:italic>P<\/jats:italic>\n                    6\n                    <jats:sub>1<\/jats:sub>\n                    . The helical self\u2010assembly of these achiral molecules is achieved due to the interplanar angle of the bis\u2010aryl molecule (\u224860\u00b0), which is fixed by directed N\u2013H\n                    <jats:bold>\u00b7\u00b7\u00b7<\/jats:bold>\n                    O\n                    <jats:sub>cr<\/jats:sub>\n                    H\u2010bonds between two H\n                    <jats:sub>amino<\/jats:sub>\n                    atoms with two O\n                    <jats:sub>cr<\/jats:sub>\n                    atoms at both ends of the molecule. Cocrystallization of octafluorobiphenol results in the formation of a crystalline hydrate based on the water\u2010mediated H\u2010bond Ar\u2010O\u2010H\u00b7\u00b7\u00b7O(H)\u2010H\u00b7\u00b7\u00b7O\n                    <jats:sub>cr<\/jats:sub>\n                    . Flexible water linker eliminates the effect of the H\u2010donor coformer structure and makes this cocrystal achiral. The hydrogen bonding details between octafluorobenzidine and 18\u2010crown\u20106 within a unit cell are investigated through a combination of vibrational spectroscopy and quantum mechanical calculations. An oxygen atom in 18\u2010crown\u20106 is identified as a chiral center, as a result of intermolecular interactions involving this atom and hydrogen atoms bonded to its\n                    <jats:italic>\u03b1<\/jats:italic>\n                    and\n                    <jats:italic>\u03b2<\/jats:italic>\n                    carbon atoms. The unique interaction patterns of 18\u2010crown\u20106 with acetone and chloroform, along with scanning electron microscopic images, reveal the role of solvent molecules in determining the chirality of the self\u2010assembly.\n                  <\/jats:p>","DOI":"10.1002\/cplu.202500481","type":"journal-article","created":{"date-parts":[[2025,9,15]],"date-time":"2025-09-15T11:55:31Z","timestamp":1757937331000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Crown Ether\u2013Promoted Helical Self\u2010Assembly of Achiral Molecules: Symmetry Breaking in Cocrystallization of Octafluorobenzidine with 18\u2010Crown\u20106"],"prefix":"10.1002","volume":"90","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9076-8720","authenticated-orcid":false,"given":"Tamara","family":"Vaganova","sequence":"first","affiliation":[{"name":"Laboratory of Heterocyclic Compounds N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry Siberian Branch of the Russian Academy of Sciences  9 Lavrentiev Avenue Novosibirsk 630090 Russian Federation"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yurij","family":"Gatilov","sequence":"additional","affiliation":[{"name":"Center of Spectral Research N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry Siberian Branch of the Russian Academy of Sciences  9 Lavrentiev Avenue Novosibirsk 630090 Russian Federation"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4614-1568","authenticated-orcid":false,"given":"Enrico","family":"Benassi","sequence":"additional","affiliation":[{"name":"Infochemistry Scientific Center ITMO University  Saint\u2010Petersburg 191002 Russian Federation"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8537-1825","authenticated-orcid":false,"given":"Haiyan","family":"Fan","sequence":"additional","affiliation":[{"name":"Department of Chemistry School of Sciences and Humanities Nazarbayev University  Qabanbay Batyr 53 Nursultan 010000 Kazakhstan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Denis","family":"Pishchur","sequence":"additional","affiliation":[{"name":"Laboratory of Physical Chemistry of Condensed Matter Nikolaev Institute of Inorganic Chemistry Siberian Branch of the Russian Academy of Sciences  3 Lavrentiev Avenue Novosibirsk 630090 Russian Federation"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Evgenij","family":"Malykhin","sequence":"additional","affiliation":[{"name":"Laboratory of Heterocyclic Compounds N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry Siberian Branch of the Russian Academy of Sciences  9 Lavrentiev Avenue Novosibirsk 630090 Russian Federation"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,9,15]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/b511119f"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr2003147"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CE00776C"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00308C"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00677"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00599"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aan3256"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.201803147"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/adom.202202811"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC06861A"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja030299w"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.105.115702"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2020.128362"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC08277D"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CE00655E"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.8b00972"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3tb20193g"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200700534"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/b500829h"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/cg060180"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010917)40:18<3435::AID-ANIE3435>3.0.CO;2-M"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2860(99)00457-3"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1039\/b403631j"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202109987"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2019.127158"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3ce42515k"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CE00530H"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352788"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CE00081D"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.9b00829"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CE00227A"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CE00369F"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1ce05581j"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja503344b"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja204540g"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/b702072d"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/a902014d"},{"key":"e_1_2_8_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/a907608e"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/cg060117k"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2016.06.015"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2ce26796a"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201407026"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CE01109A"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11172-015-1069-1"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molstruc.2016.11.091"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CE00327B"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.8b01062"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8TC04867C"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25112701"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2020.109577"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200902816"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/cg400805c"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1080\/10610278.2013.833336"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00176a025"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39910000426"},{"key":"e_1_2_8_55_1","unstructured":"Cambridge Structural Database System2025. version 6.0 (update May)."},{"key":"e_1_2_8_56_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11172-007-0351-2"},{"key":"e_1_2_8_57_1","volume":"159","author":"Yakobson G. G.","year":"1964","journal-title":"Dokl. Akad. Nauk SSSR."},{"key":"e_1_2_8_57_2","unstructured":"b) Sintezy Ftororganicheskikh Soedinenii (monomery i Promezhutochnye Produkty) [Syntheses of Organofluorine Compounds (monomers and Intermediate Products)] I. L.Knunyants G. G.Yakobson Moscow 1977 191."},{"key":"e_1_2_8_58_1","unstructured":"SADABS version 2008\/1 Bruker AXS Inc Madison Wisconsin USA."},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053229614024218"},{"key":"e_1_2_8_60_1","volume-title":"PLATON, a Multipurpose Crystallographic Tool, Version 10M","author":"Spek A. L.","year":"2003"},{"key":"e_1_2_8_60_2","doi-asserted-by":"publisher","DOI":"10.1107\/S2053229614024929"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576719014092"},{"key":"e_1_2_8_62_1","volume-title":"APEX2","author":"Bruker","year":"2012"},{"key":"e_1_2_8_63_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10973-015-5186-8"},{"key":"e_1_2_8_64_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.saa.2022.121632"}],"container-title":["ChemPlusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cplu.202500481","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,11,12]],"date-time":"2025-11-12T06:42:15Z","timestamp":1762929735000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cplu.202500481"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,9,15]]},"references-count":67,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2025,11,10]]}},"alternative-id":["10.1002\/cplu.202500481"],"URL":"https:\/\/doi.org\/10.1002\/cplu.202500481","archive":["Portico"],"relation":{},"ISSN":["2192-6506","2192-6506"],"issn-type":[{"value":"2192-6506","type":"print"},{"value":"2192-6506","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,9,15]]},"assertion":[{"value":"2025-07-20","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-09-15","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202500481"}}