{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:49:22Z","timestamp":1740174562567,"version":"3.37.3"},"reference-count":14,"publisher":"International Union of Crystallography (IUCr)","issue":"9","license":[{"start":{"date-parts":[[2021,7,16]],"date-time":"2021-07-16T00:00:00Z","timestamp":1626393600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2021,7,16]],"date-time":"2021-07-16T00:00:00Z","timestamp":1626393600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/100005171","name":"Ohio Board of Regents","doi-asserted-by":"publisher","award":["0087210"],"award-info":[{"award-number":["0087210"]}],"id":[{"id":"10.13039\/100005171","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["0087210"],"award-info":[{"award-number":["0087210"]}],"id":[{"id":"10.13039\/100000001","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":[[2021,7,13]]},"published-print":{"date-parts":[[2021,9,1]]},"abstract":"<jats:p>Two crystallographically independent molecules are present in the asymmetric unit of the title compound, C<jats:sub>14<\/jats:sub>H<jats:sub>11<\/jats:sub>NO<jats:sub>2<\/jats:sub>, with virtually identical geometries. The carbazole units are planar. The hydroxy group at position 1, carbaldehyde group at position 2, and methyl group at position 8 (with the exception of two H atoms) are coplanar with the attached benzene rings. The dihedral angle between the two benzene rings is 2.20\u2005(9)\u00b0 in molecule <jats:italic>A<\/jats:italic> and 2.01\u2005(9)\u00b0 in molecule <jats:italic>B<\/jats:italic>. The pyrrole ring makes dihedral angles of 0.82\u2005(10) and 1.40\u2005(10)\u00b0 [0.84\u2005(10) and 1.18\u2005(10)\u00b0 in molecule <jats:italic>B<\/jats:italic>] with the (\u2013CH<jats:sub>3<\/jats:sub>)-substituted and (\u2013OH and \u2013CHO) substituted benzene rings, respectively. The molecular structure is stabilized by the intramolecular O\u2014H...O hydrogen bonds, while the crystal structure features N\u2014H...O and C\u2014H...O hydrogen bonds. A range of \u03c0\u2013\u03c0 contacts further stabilizes the crystal structure.<\/jats:p>","DOI":"10.1107\/s2056989021007210","type":"journal-article","created":{"date-parts":[[2021,7,16]],"date-time":"2021-07-16T08:09:36Z","timestamp":1626422976000},"page":"867-870","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and crystal structure of 1-hydroxy-8-methyl-9<i>H<\/i>-carbazole-2-carbaldehyde"],"prefix":"10.1107","volume":"77","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9896-186X","authenticated-orcid":true,"given":"Aravazhi Amalan","family":"Thiruvalluvar","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"M.","family":"Sridharan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"K. J.","family":"Rajendra Prasad","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3305-852X","authenticated-orcid":true,"given":"M.","family":"Zeller","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2021,7,16]]},"reference":[{"key":"yy2001_bb1","doi-asserted-by":"crossref","first-page":"o3146","DOI":"10.1107\/S1600536810045769","volume":"66","author":"Archana","year":"2010","journal-title":"Acta Cryst. E"},{"key":"yy2001_bb2","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."},{"unstructured":"Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.","key":"yy2001_bb3"},{"key":"yy2001_bb4","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"yy2001_bb5","doi-asserted-by":"crossref","first-page":"o2682","DOI":"10.1107\/S160053680701954X","volume":"63","author":"Gunaseelan","year":"2007","journal-title":"Acta Cryst. E"},{"key":"yy2001_bb6","doi-asserted-by":"crossref","first-page":"4303","DOI":"10.1021\/cr020059j","volume":"102","author":"Kn\u00f6lker","year":"2002","journal-title":"Chem. Rev."},{"doi-asserted-by":"crossref","unstructured":"Shanmugasundaram, K. & Rajendra Prasad, K. J. (1999). Heterocycles, 51, 9, 2163-2169.","key":"yy2001_bb7","DOI":"10.3987\/COM-99-8587"},{"key":"yy2001_bb8","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"yy2001_bb9","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"yy2001_bb10","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1107\/S2056989019016244","volume":"76","author":"Spek","year":"2020","journal-title":"Acta Cryst. E"},{"key":"yy2001_bb11","doi-asserted-by":"crossref","first-page":"572","DOI":"10.3184\/030823408X361110","author":"Sridharan","year":"2008","journal-title":"J. Chem. Res."},{"unstructured":"Sridharan, M. & Rajendra Prasad, K. J. (2011). J. Chem. Res. 53-59.","key":"yy2001_bb12"},{"key":"yy2001_bb13","doi-asserted-by":"crossref","first-page":"o2157","DOI":"10.1107\/S1600536808033862","volume":"64","author":"Sridharan","year":"2008","journal-title":"Acta Cryst. E"},{"key":"yy2001_bb14","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Cryst."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2021\/09\/00\/yy2001\/yy2001.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2021\/09\/00\/yy2001\/yy2001.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T10:36:29Z","timestamp":1736764589000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989021007210"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,7,16]]},"references-count":14,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2021,9]]}},"alternative-id":["S2056989021007210"],"URL":"https:\/\/doi.org\/10.1107\/s2056989021007210","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989021007210\/yy2001sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989021007210\/yy2001Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989021007210\/yy2001Isup3.cdx","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989021007210\/yy2001Isup4.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"type":"electronic","value":"2056-9890"}],"subject":[],"published":{"date-parts":[[2021,7,16]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","order":0,"name":"journal","label":"Publication","explanation":{"URL":"http:\/\/journals.iucr.org\/e"},"group":{"name":"general","label":"General"}},{"value":"research communications","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/e\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?yy2001","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":"21 June 2021","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"13 July 2021","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"16 July 2021","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?yy2001"}},{"value":"\u00a9 2021 Thiruvalluvar et al.","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}},{"value":"Creative Commons Attribution (CC-BY)","order":1,"name":"license","label":"Licence","explanation":{"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}}]}}