{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T08:53:10Z","timestamp":1791276790783,"version":"4.1.0"},"reference-count":43,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T00:00:00Z","timestamp":1791244800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T00:00:00Z","timestamp":1791244800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["RI\u20101063\/17\u20101"],"award-info":[{"award-number":["RI\u20101063\/17\u20101"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["RI\u20101063\/22\u20101"],"award-info":[{"award-number":["RI\u20101063\/22\u20101"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Packing into a crystal lattice is not easy for flexible molecules with an irregular shape, as all molecules have to adopt the same conformation in order to fit into the same position of a well\u2010ordered lattice. When numerous conformations are populated at the crystallization temperature, crystal growth can be impaired. The larger and more flexible the analyte to be crystallized, the greater the challenge to obtain single crystals suitable for x\u2010ray crystallography. Here we show how vitamin K\n                    <jats:sub>2<\/jats:sub>\n                    , a natural product with a rigid, bicyclic menaquinone head group and a long flexible terpenoid chain, can be crystallized. A second\u2010generation chaperone and an optimized protocol gave co\u2010crystals that diffract to a resolution of 0.8 \u00c5. The chaperone employed was 1,3,5,7\u2010tetrakis(2\u2010fluoro\u20104\u2010methoxyphenyl)adamantane (TFM). The protocol involved seeding with crystals selected from the conglomerate of an initial run, and a three\u2010stage temperature protocol. The x\u2010ray crystal structure shows layers of chaperones and vitamin K\n                    <jats:sub>2<\/jats:sub>\n                    molecules, with back\u2010folding of the terpene chains of the latter. Together with another structure showing layers of chaperone and solvent, this confirms that tetraaryladamantanes can facilitate crystallization in more ways than by just filling voids in their packing arrangements.\n                  <\/jats:p>","DOI":"10.1002\/chem.71741","type":"journal-article","created":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T08:26:47Z","timestamp":1791275207000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Getting the Big Ones to Pack: Crystal Structure of Vitamin K\n                    <sub>2<\/sub>\n                    With a Chaperone"],"prefix":"10.1002","author":[{"given":"Jan","family":"Hartenfels","sequence":"first","affiliation":[{"name":"Institut F\u00fcr Organische Chemie Universit\u00e4t Stuttgart  Stuttgart Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Greta L\u00edlia","family":"Runge\u2010Seither","sequence":"additional","affiliation":[{"name":"Institut F\u00fcr Organische Chemie Universit\u00e4t Stuttgart  Stuttgart Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tim","family":"Berking","sequence":"additional","affiliation":[{"name":"Institut F\u00fcr Organische Chemie Universit\u00e4t Stuttgart  Stuttgart Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Johanna","family":"Osterbrink","sequence":"additional","affiliation":[{"name":"Institut F\u00fcr Organische Chemie Universit\u00e4t Stuttgart  Stuttgart Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carsten","family":"Wolf","sequence":"additional","affiliation":[{"name":"Bruker AXS SE  Karlsruhe Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6907-0205","authenticated-orcid":false,"given":"Clemens","family":"Richert","sequence":"additional","affiliation":[{"name":"Institut F\u00fcr Organische Chemie Universit\u00e4t Stuttgart  Stuttgart Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,10,6]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"crossref","DOI":"10.1007\/978-3-662-06431-3","volume-title":"Crystal Structure Determination","author":"Massa W.","year":"2004"},{"key":"e_1_2_8_3_1","article-title":"Development of an Efficient Stereoretentive Para\u2010Claisen\u2010Cope Rearrangement","volume":"3","author":"Breinsperger J.","year":"2025","journal-title":"Chemistry Europe"},{"key":"e_1_2_8_4_1","doi-asserted-by":"crossref","first-page":"2143","DOI":"10.1021\/jo00952a006","article-title":"Correlation of Configuration and Fluorine\u201019 Chemical Shifts of Alpha\u2010methoxy\u2010alpha\u2010trifluoromethylphenyl Acetate Derivatives","volume":"12","author":"Sullivan G. 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