{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T10:03:42Z","timestamp":1790330622806,"version":"4.1.0"},"reference-count":38,"publisher":"International Union of Crystallography (IUCr)","issue":"7","license":[{"start":{"date-parts":[[2026,6,23]],"date-time":"2026-06-23T00:00:00Z","timestamp":1782172800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2026,6,23]],"date-time":"2026-06-23T00:00:00Z","timestamp":1782172800000},"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":[[2026,6,12]]},"published-print":{"date-parts":[[2026,7,1]]},"abstract":"<jats:p>\n                    The title compound, C\n                    <jats:sub>10<\/jats:sub>\n                    H\n                    <jats:sub>14<\/jats:sub>\n                    N\n                    <jats:sub>3<\/jats:sub>\n                    OBr, was prepared by a nucleophilic aromatic substitution reaction between 2,6-dimethylmorpholine and 2-chloropyrimidine, followed by bromination of the pyrimidine ring. The compound crystallizes in the monoclinic system (space group\n                    <jats:italic>P<\/jats:italic>\n                    2\n                    <jats:sub>1<\/jats:sub>\n                    \/c) with four molecules in the unit cell (\n                    <jats:italic>Z<\/jats:italic>\n                    = 4). The molecule exhibits approximate\n                    <jats:italic>C<\/jats:italic>\n                    <jats:sub>S<\/jats:sub>\n                    point-group symmetry (r.m.s. deviation: 0.1072\u2005\u00c5). The arrangement of the molecules in the solid state is dominated by close packing. C\u2014H...N contacts between pyrimidinyl rings in adjacent molecules with an\n                    <jats:italic>R<\/jats:italic>\n                    <jats:sup>2<\/jats:sup>\n                    <jats:sub>2<\/jats:sub>\n                    (6) motif are encountered, whereas the bromine atom does not exhibit any short contacts that could be regarded as halogen bonds.\n                  <\/jats:p>","DOI":"10.1107\/s2056989026006158","type":"journal-article","created":{"date-parts":[[2026,6,15]],"date-time":"2026-06-15T13:23:58Z","timestamp":1781529838000},"page":"768-772","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structure of the\n                    <i>meso<\/i>\n                    compound (2\n                    <i>R<\/i>\n                    ,6\n                    <i>S<\/i>\n                    )-4-(5-bromopyrimidin-2-yl)-2,6-dimethylmorpholine"],"prefix":"10.1107","volume":"82","author":[{"given":"Paul R.","family":"Palme","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0357-3173","authenticated-orcid":true,"given":"Richard","family":"Goddard","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8171-9399","authenticated-orcid":true,"given":"Markus","family":"Leutzsch","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0062-7896","authenticated-orcid":true,"given":"Adrian","family":"Richter","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"Imming","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3438-4666","authenticated-orcid":true,"given":"R\u00fcdiger W.","family":"Seidel","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2026,6,23]]},"reference":[{"key":"meu2003_bb1","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1107\/S0108768110012048","volume":"66","author":"Allen","year":"2010","journal-title":"Acta Cryst. B"},{"key":"meu2003_bb2","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"meu2003_bb3","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":"meu2003_bb4","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1021\/j100785a001","volume":"68","author":"Bondi","year":"1964","journal-title":"J. Phys. Chem."},{"key":"meu2003_bb5","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1107\/S2053273314022207","volume":"71","author":"Bourhis","year":"2015","journal-title":"Acta Cryst. A"},{"key":"meu2003_bb6","unstructured":"Brandenburg, K. (2018). DIAMOND. Crystal Impact GbR, Bonn, Germany."},{"key":"meu2003_bb7","doi-asserted-by":"crossref","first-page":"425","DOI":"10.1002\/mrc.1270010602","volume":"1","author":"Br\u00fcgel","year":"1969","journal-title":"Org. Magn. Reson."},{"key":"meu2003_bb8","unstructured":"Bruker (2019). SAINT. Bruker AXS LLC, Madison, Wisconsin, USA."},{"key":"meu2003_bb9","unstructured":"Bruker (2024). APEX6. Bruker AXS LLC, Madison, Wisconsin, USA."},{"key":"meu2003_bb10","doi-asserted-by":"crossref","first-page":"1350","DOI":"10.1007\/s11172-014-0602-y","volume":"63","author":"Cheprakova","year":"2014","journal-title":"Russ. Chem. Bull."},{"key":"meu2003_bb11","doi-asserted-by":"crossref","first-page":"2311","DOI":"10.1002\/anie.199523111","volume":"34","author":"Desiraju","year":"1995","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"meu2003_bb12","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"meu2003_bb13","doi-asserted-by":"crossref","first-page":"766","DOI":"10.1007\/s10593-013-1308-z","volume":"49","author":"Gorbunov","year":"2013","journal-title":"Chem. Heterocycl. Cmpd"},{"key":"meu2003_bb14","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"meu2003_bb15","doi-asserted-by":"crossref","first-page":"18936","DOI":"10.1039\/D5SC00912J","volume":"16","author":"Hall","year":"2025","journal-title":"Chem. Sci."},{"key":"meu2003_bb16","unstructured":"Hanyu, N., Saito, T., Shibata, T., Sato, K. & Ogino, K. (2009). Shiseido Co Ltd. WO20090991912A1."},{"key":"meu2003_bb17","unstructured":"Heng, R., Koch, G., Schlapbach, A. & Seiler, M. P. (2008). Novartis A.-G. WO2008034600A1."},{"key":"meu2003_bb18","doi-asserted-by":"crossref","first-page":"1132","DOI":"10.1007\/s11426-022-1507-2","volume":"66","author":"Jiang","year":"2023","journal-title":"Sci. China Chem."},{"key":"meu2003_bb19","unstructured":"Kitajgorodskij, A. I. (1973). Molecular crystals and molecules. New York: Academic Press."},{"key":"meu2003_bb20","doi-asserted-by":"crossref","first-page":"1675","DOI":"10.1039\/D0SC05526C","volume":"12","author":"Kleemiss","year":"2021","journal-title":"Chem. Sci."},{"key":"meu2003_bb21","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S1600576714022985","volume":"48","author":"Krause","year":"2015","journal-title":"J. Appl. Cryst."},{"key":"meu2003_bb22","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"meu2003_bb23","doi-asserted-by":"crossref","first-page":"519","DOI":"10.1107\/S2053273321009086","volume":"77","author":"Midgley","year":"2021","journal-title":"Acta Cryst. A"},{"key":"meu2003_bb24","doi-asserted-by":"crossref","unstructured":"Neese, F. (2025). WIREs Comput. Mol. Sci. 15, e70019.","DOI":"10.1002\/wcms.70019"},{"key":"meu2003_bb25","doi-asserted-by":"crossref","first-page":"25274","DOI":"10.1021\/acs.jmedchem.5c02284","volume":"68","author":"Palme","year":"2025","journal-title":"J. Med. Chem."},{"key":"meu2003_bb26","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"meu2003_bb27","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"meu2003_bb28","unstructured":"Shojaei, F., Fang, C., Semple, J. E. & Gillings, M. (2023). Huyabio International LLC. WO2023177592A1."},{"key":"meu2003_bb29","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1039\/B818330A","volume":"11","author":"Spackman","year":"2009","journal-title":"CrystEngComm"},{"key":"meu2003_bb30","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.1107\/S1600576721002910","volume":"54","author":"Spackman","year":"2021","journal-title":"J. Appl. Cryst."},{"key":"meu2003_bb31","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1107\/S090744490804362X","volume":"65","author":"Spek","year":"2009","journal-title":"Acta Cryst. D"},{"key":"meu2003_bb32","doi-asserted-by":"crossref","first-page":"7142","DOI":"10.1002\/ejoc.201901364","volume":"2019","author":"Wei","year":"2019","journal-title":"Eur. J. Org. Chem."},{"key":"meu2003_bb33","doi-asserted-by":"crossref","first-page":"3297","DOI":"10.1039\/b508541a","volume":"7","author":"Weigend","year":"2005","journal-title":"Phys. Chem. Chem. Phys."},{"key":"meu2003_bb34","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Cryst."},{"key":"meu2003_bb35","unstructured":"Wu, H., Lin, J., Li, Y., Wei, C. & Chen, S. (2015). Medshine Discovery Inc. CN104945377 A."},{"key":"meu2003_bb36","unstructured":"Yoshihara, K., Suzuki, D., Yamaki, S., Koga, Y., Seki, N., Fujiyasu, J. & Neya, M. (2011). Astellas Pharma Inc. WO2011034078A1."},{"key":"meu2003_bb37","unstructured":"You, Q., Guo, X., Shojaei, F., Chen, X., Semple, J. E., Jiang, Z., Xu, X. & Gillings, M. (2023). Huyabio International LLC, China Pharmaceutical University. US20230286925A1."},{"key":"meu2003_bb38","doi-asserted-by":"crossref","first-page":"4877","DOI":"10.1021\/acs.orglett.4c01315","volume":"26","author":"Yuan","year":"2024","journal-title":"Org. Lett."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2026\/07\/00\/meu2003\/meu2003.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2026\/07\/00\/meu2003\/meu2003.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T09:28:38Z","timestamp":1790328518000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989026006158"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,6,23]]},"references-count":38,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2026,7]]}},"alternative-id":["S2056989026006158"],"URL":"https:\/\/doi.org\/10.1107\/s2056989026006158","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989026006158\/meu2003sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026006158\/meu2003Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026006158\/meu2003Isup3.cdx","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026006158\/meu2003sup4.pdf","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026006158\/meu2003sup5.pdf","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026006158\/meu2003sup6.pdf","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,6,23]]},"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?meu2003","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 May 2026","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"12 June 2026","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"23 June 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?meu2003"}},{"value":"\u00a9 2026 Palme\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"}}]}}