{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,31]],"date-time":"2026-03-31T18:53:29Z","timestamp":1774983209398,"version":"3.50.1"},"reference-count":0,"publisher":"International Union of Crystallography (IUCr)","issue":"1","license":[{"start":{"date-parts":[[2026,2,1]],"date-time":"2026-02-01T00:00:00Z","timestamp":1769904000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2026,2,1]],"date-time":"2026-02-01T00:00:00Z","timestamp":1769904000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"funder":[{"name":"Program for Development of Basic Science (PEDECIBA), Uruguay."}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr B Struct Sci Cryst Eng Mater","Acta Crystallogr B","Acta Crystallogr B Struct Sci","Acta Cryst B","Acta Cryst B Struct Sci Cryst Eng Mater","Acta Cryst Sect B","Acta Cryst Sect B Struct Sci Cryst Eng Mater","Acta Crystallogr Sect B","Acta Crystallogr Sect B Struct Sci Cryst Eng Mater","Acta Crystallogr Sect B Struct Sci"],"accepted":{"date-parts":[[2025,11,18]]},"published-print":{"date-parts":[[2026,2,1]]},"abstract":"<jats:p>\n                    The crystal structures of two polymorphs of lapachol [2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione, C\n                    <jats:sub>15<\/jats:sub>\n                    H\n                    <jats:sub>14<\/jats:sub>\n                    O\n                    <jats:sub>3<\/jats:sub>\n                    ] \u2013 a natural pigment relevant in traditional medicine and of considerable scientific interest due to its broad spectrum of biological and pharmacological activities \u2013 one with triclinic (\n                    <jats:italic>P<\/jats:italic>\n                    <jats:overline>1<\/jats:overline>\n                    )and the other with monoclinic (\n                    <jats:italic>P<\/jats:italic>\n                    2\n                    <jats:sub>1<\/jats:sub>\n                    \/\n                    <jats:italic>c<\/jats:italic>\n                    ) space-group symmetries have been redetermined and are compared with a newly identified form, also monoclinic. The three crystal structures are polytypes since they share dimeric layers of hydrogen-bonded lapachol molecules, which connect through \u03c0-stacking within a layer. Adjacent layers in the three compounds are held together by weak van der Waals forces between allylic side chains. However, they adopt distinct stacking modes: successive layers are translated along the\n                    <jats:italic>c<\/jats:italic>\n                    axis in the triclinic form, translated and rotated 90\u00b0 along the\n                    <jats:italic>b<\/jats:italic>\n                    axis in the first monoclinic form and translated and rotated 90\u00b0 along the\n                    <jats:italic>a<\/jats:italic>\n                    axis in the new monoclinic form. These variations in interlayer arrangement, arising from different relative orientations of interacting allylic moieties, result in subtle differences in the density of the three forms.\n                  <\/jats:p>","DOI":"10.1107\/s2052520625010376","type":"journal-article","created":{"date-parts":[[2025,12,19]],"date-time":"2025-12-19T18:17:25Z","timestamp":1766168245000},"page":"54-60","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Three polytypes of lapachol, a natural pigment with promising pharmacological properties"],"prefix":"10.1107","volume":"82","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3487-8335","authenticated-orcid":true,"given":"Natasha","family":"Di Benedetto","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mario A.","family":"Mac\u00edas","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Noelia","family":"M\u00e9ndez","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Miguel","family":"Mart\u00ednez Cabrera","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7606-8074","authenticated-orcid":true,"given":"Leopoldo","family":"Suescun","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2026,2,1]]},"updated-by":[{"DOI":"10.1107\/s205252062600329x","type":"correction","label":"Correction","source":"publisher","updated":{"date-parts":[[2026,4,1]],"date-time":"2026-04-01T00:00:00Z","timestamp":1775001600000}}],"container-title":["Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/b\/issues\/2026\/01\/00\/aw5103\/aw5103.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/b\/issues\/2026\/01\/00\/aw5103\/aw5103.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,2,3]],"date-time":"2026-02-03T14:09:03Z","timestamp":1770127743000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2052520625010376"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,2,1]]},"references-count":0,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2026,2]]}},"alternative-id":["S2052520625010376"],"URL":"https:\/\/doi.org\/10.1107\/s2052520625010376","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2052520625010376\/aw5103sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2052520625010376\/aw5103LAPAIsup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2052520625010376\/aw5103LAPAIIsup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2052520625010376\/aw5103LAPAIIIsup4.hkl","asserted-by":"subject"}]},"ISSN":["2052-5206"],"issn-type":[{"value":"2052-5206","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,2,1]]},"assertion":[{"value":"Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials","order":0,"name":"journal","label":"Publication","explanation":{"URL":"https:\/\/journals.iucr.org\/b"},"group":{"name":"general","label":"General"}},{"value":"research papers","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/b\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?aw5103","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":"13 August 2025","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"18 November 2025","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"1 February 2026","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?aw5103"}},{"value":"\u00a9 Natasha Di Benedetto\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 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