{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T00:03:05Z","timestamp":1787011385654,"version":"build-2736575974"},"reference-count":19,"publisher":"International Union of Crystallography (IUCr)","issue":"4","license":[{"start":{"date-parts":[[2026,3,27]],"date-time":"2026-03-27T00:00:00Z","timestamp":1774569600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2026,3,27]],"date-time":"2026-03-27T00:00:00Z","timestamp":1774569600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"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":[[2026,3,23]]},"published-print":{"date-parts":[[2026,4,1]]},"abstract":"<jats:p>\n                    In the title compound, C\n                    <jats:sub>20<\/jats:sub>\n                    H\n                    <jats:sub>23<\/jats:sub>\n                    ClN\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    , the cyclooctene ring has a boat\u2013chair conformation. The ethyl formate moiety is equally disordered over two positions. The dihedral angle between the pyridine and chlorophenyl rings is 81.33\u2005(13)\u00b0. An intramolecular N\u2014H...O hydrogen bond helps to stabilize the molecular conformation. In the crystal, N\u2014H...N hydrogen-bonding leads to the formation of dimers with an\n                    <jats:italic>R<\/jats:italic>\n                    <jats:sub>2<\/jats:sub>\n                    <jats:sup>2<\/jats:sup>\n                    (8) graph-set motif. Additional consolidation of the packing in the crystal is achieved through C\u2014H...\u03c0 and \u03c0\u2013\u03c0 stacking interactions. The intermolecular interactions were quantified and analysed using Hirshfeld surface analysis, revealing that H...H interactions contribute by far the most to the crystal packing (63.6%).\n                  <\/jats:p>","DOI":"10.1107\/s2056989026003087","type":"journal-article","created":{"date-parts":[[2026,3,24]],"date-time":"2026-03-24T06:32:41Z","timestamp":1774333961000},"page":"413-417","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Crystal structure and Hirshfeld surface analysis of ethyl 2-amino-4-(4-chlorophenyl)-5,6,7,8,9,10-hexahydrocycloocta[\n                    <i>b<\/i>\n                    ]pyridine-3-carboxylate"],"prefix":"10.1107","volume":"82","author":[{"given":"Srinivasan","family":"Pazhamalai","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/01x24z140","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chandiran","family":"Jayakodi","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/01x24z140","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Velayutham","family":"Mahalakshmi","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/01x24z140","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rajendran Arivu","family":"Selvan","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/01x24z140","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sivashanmugam","family":"Selvanayagam","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2026,3,27]]},"reference":[{"key":"wm5792_bb13","first-page":"5800","volume":"80","author":"Bagley","year":"2015","journal-title":"J. Org. Chem."},{"key":"wm5792_bb1","first-page":"e1600244","volume":"350","author":"Bekhit","year":"2017","journal-title":"Arch. Pharm."},{"key":"wm5792_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."},{"key":"wm5792_bb3","unstructured":"Bruker (2017). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, U. S. A."},{"key":"wm5792_bb4","first-page":"451","volume":"75","author":"El-Gazzar","year":"2021","journal-title":"Chem. Pap."},{"key":"wm5792_bb5","doi-asserted-by":"crossref","first-page":"256","DOI":"10.1107\/S0108768189012929","volume":"46","author":"Etter","year":"1990","journal-title":"Acta Cryst. B"},{"key":"wm5792_bb6","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1107\/S0108768188008730","volume":"44","author":"Evans","year":"1988","journal-title":"Acta Cryst. B"},{"key":"wm5792_bb7","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0021889812029111","volume":"45","author":"Farrugia","year":"2012","journal-title":"J. Appl. Cryst."},{"key":"wm5792_bb8","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S1600576714022985","volume":"48","author":"Krause","year":"2015","journal-title":"J. Appl. Cryst."},{"key":"wm5792_bb9","doi-asserted-by":"crossref","first-page":"3814","DOI":"10.1039\/b704980c","author":"McKinnon","year":"2007","journal-title":"Chem. Commun."},{"key":"wm5792_bb10","doi-asserted-by":"crossref","first-page":"3211","DOI":"10.3390\/molecules25143211","volume":"25","author":"Shaaban","year":"2020","journal-title":"Molecules"},{"key":"wm5792_bb11","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"wm5792_bb12","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"wm5792_bb14","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1039\/B818330A","volume":"11","author":"Spackman","year":"2009","journal-title":"CrystEngComm"},{"key":"wm5792_bb15","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1039\/B203191B","volume":"4","author":"Spackman","year":"2002","journal-title":"CrystEngComm"},{"key":"wm5792_bb16","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.1107\/S1600576721002910","volume":"54","author":"Spackman","year":"2021","journal-title":"J. Appl. Cryst."},{"key":"wm5792_bb17","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1107\/S2056989019016244","volume":"76","author":"Spek","year":"2020","journal-title":"Acta Cryst. E"},{"key":"wm5792_bb23","doi-asserted-by":"crossref","first-page":"1111","DOI":"10.2217\/fmb.15.39","volume":"10","author":"Van Bambeke","year":"2015","journal-title":"Fut. Microbiol."},{"key":"wm5792_bb19","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":"https:\/\/journals.iucr.org\/e\/issues\/2026\/04\/00\/wm5792\/wm5792.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2026\/04\/00\/wm5792\/wm5792.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,4,7]],"date-time":"2026-04-07T16:01:14Z","timestamp":1775577674000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989026003087"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,3,27]]},"references-count":19,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2026,4]]}},"alternative-id":["S2056989026003087"],"URL":"https:\/\/doi.org\/10.1107\/s2056989026003087","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989026003087\/wm5792sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026003087\/wm5792Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026003087\/wm5792Isup3.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,3,27]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","order":0,"name":"journal","label":"Publication","explanation":{"URL":"https:\/\/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?wm5792","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":"2 March 2026","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"23 March 2026","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"27 March 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?wm5792"}},{"value":"\u00a9 2026 Pazhamalai\n                      et al.","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"https:\/\/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"}}]}}