{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:49:31Z","timestamp":1740174571412,"version":"3.37.3"},"reference-count":42,"publisher":"International Union of Crystallography (IUCr)","issue":"4","license":[{"start":{"date-parts":[[2022,3,15]],"date-time":"2022-03-15T00:00:00Z","timestamp":1647302400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2022,3,15]],"date-time":"2022-03-15T00:00:00Z","timestamp":1647302400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/100000086","name":"National Science Foundation, Directorate for Mathematical and Physical Sciences","doi-asserted-by":"publisher","award":["CHE-1625543","CHE-1800361"],"award-info":[{"award-number":["CHE-1625543","CHE-1800361"]}],"id":[{"id":"10.13039\/100000086","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"accepted":{"date-parts":[[2022,3,10]]},"published-print":{"date-parts":[[2022,4,1]]},"abstract":"<jats:p>The title chlorin, <jats:bold>2<jats:sup>Ph<\/jats:sup>H<jats:sub>2<\/jats:sub>\n                  <\/jats:bold>, hydrogen-bonded to dimethylaminopyridine (DMAP), C<jats:sub>44<\/jats:sub>H<jats:sub>32<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>2<\/jats:sub>\u00b7C<jats:sub>7<\/jats:sub>H<jats:sub>10<\/jats:sub>N<jats:sub>2<\/jats:sub>, and its corresponding zinc(II) complex, <jats:bold>2<jats:sup>Ph<\/jats:sup>Zn<\/jats:bold>, axially coordinated to ethylenediamine (EDA), [Zn(C<jats:sub>44<\/jats:sub>H<jats:sub>30<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>2<\/jats:sub>)]\u00b7C<jats:sub>2<\/jats:sub>H<jats:sub>8<\/jats:sub>N<jats:sub>2<\/jats:sub>, were isolated and crystallized by adventitious reduction of the corresponding osmate esters by DMAP and EDA, respectively. Known since 1996 and, <jats:italic>inter alia<\/jats:italic>, used for the preparation of a wide range of (planar and non-planar) chlorin analogues (so-called pyrrole-modified porphyrins), their conformational analyses in the solid state are important benchmarks. Both macrocycles are only modestly distorted from planarity and both are slightly more non-planar than the corresponding dimethoxy-derivative, but less planar than a free-base <jats:italic>meso<\/jats:italic>-pentafluorophenyl-based osmate ester. NSD analyses provide quantitative and qualitative analyses of the distortion modes. One origin of the non-planarity is presumably the avoidance of the eclipsed configuration of the two <jats:italic>vic\u2013cis<\/jats:italic> diols on the pyrroline moiety; the resulting deformation of the pyrroline translates in some cases into the macrocycle. The structure of <jats:bold>2<jats:sup>Ph<\/jats:sup>H<jats:sub>2<\/jats:sub>\n                  <\/jats:bold> features voids making up <jats:italic>ca<\/jats:italic> 26% of the unit-cell volume filled with highly disordered solvate molecules (chloroform and hexanes). <jats:bold>2<jats:sup>Ph<\/jats:sup>Zn<\/jats:bold> crystallized with a 13.6\u2005(4)% occupied solvate methanol molecule.<\/jats:p>","DOI":"10.1107\/s2056989022002729","type":"journal-article","created":{"date-parts":[[2022,3,15]],"date-time":"2022-03-15T09:21:44Z","timestamp":1647336104000},"page":"392-398","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["Crystal structure of <i>cis<\/i>-7,8-dihydroxy-5,10,15,20-tetraphenylchlorin and its zinc(II)\u2013ethylenediamine complex"],"prefix":"10.1107","volume":"78","author":[{"given":"Nivedita","family":"Chaudhri","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1560-7345","authenticated-orcid":true,"given":"Christian","family":"Br\u00fcckner","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Matthias","family":"Zeller","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2022,3,15]]},"reference":[{"key":"dj2044_bb1","doi-asserted-by":"crossref","first-page":"576","DOI":"10.1142\/S1088424612500654","volume":"16","author":"Banerjee","year":"2012","journal-title":"J. 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