{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:48:54Z","timestamp":1740174534646,"version":"3.37.3"},"reference-count":19,"publisher":"International Union of Crystallography (IUCr)","issue":"7","license":[{"start":{"date-parts":[[2019,6,14]],"date-time":"2019-06-14T00:00:00Z","timestamp":1560470400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2019,6,14]],"date-time":"2019-06-14T00:00:00Z","timestamp":1560470400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/501100008982","name":"National Science Foundation","doi-asserted-by":"publisher","award":["MRI CHE-1725699","REU CHE-1092944"],"award-info":[{"award-number":["MRI CHE-1725699","REU CHE-1092944"]}],"id":[{"id":"10.13039\/501100008982","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100008117","name":"Grand Valley State University","doi-asserted-by":"crossref","id":[{"id":"10.13039\/100008117","id-type":"DOI","asserted-by":"crossref"}]}],"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":[[2019,6,6]]},"published-print":{"date-parts":[[2019,7,1]]},"abstract":"<jats:p>Two bis-carbamoylmethylphosphine oxide compounds, namely {[(3-{[2-(diphenylphosphinoyl)ethanamido]methyl}benzyl)carbamoyl]methyl}diphenylphosphine oxide, C<jats:sub>36<\/jats:sub>H<jats:sub>34<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>4<\/jats:sub>P<jats:sub>2<\/jats:sub>, (I), and diethyl [({2-[2-(diethoxyphosphinoyl)ethanamido]ethyl}carbamoyl)methyl]phosphonate, C<jats:sub>14<\/jats:sub>H<jats:sub>30<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>8<\/jats:sub>P<jats:sub>2<\/jats:sub>, (II), were synthesized <jats:italic>via<\/jats:italic> nucleophilic acyl substitution reactions between an ester and a primary amine. Hydrogen-bonding interactions are present in both crystals, but these interactions are intramolecular in the case of compound (I) and intermolecular in compound (II). Intramolecular \u03c0\u2013\u03c0 stacking interactions are also present in the crystal of compound (I) with a centroid\u2013centroid distance of 3.9479\u2005(12)\u2005\u00c5 and a dihedral angle of 9.56\u2005(12)\u00b0. Intermolecular C\u2014H...\u03c0 interactions [C...centroid distance of 3.622\u2005(2)\u2005\u00c5, C\u2014H...centroid angle of 146\u00b0] give rise to supramolecular sheets that lie in the <jats:italic>ab<\/jats:italic> plane. Key geometric features for compound (I) involve a nearly planar, <jats:italic>trans-<\/jats:italic>amide group with a C\u2014N\u2014C\u2014C torsion angle of 169.12\u2005(17)\u00b0, and a torsion angle of \u2212108.39\u2005(15)\u00b0 between the phosphine oxide phosphorus atom and the amide nitrogen atom. For compound (II), the electron density corresponding to the phosphoryl group was disordered, and was modeled as two parts with a 0.7387\u2005(19):0.2613\u2005(19) occupancy ratio. Compound (II) also boasts a <jats:italic>trans<\/jats:italic>-amide group that approaches planarity with a C\u2014N\u2014C\u2014C torsion angle of \u2212176.50\u2005(16)\u00b0. The hydrogen bonds in this structure are intermolecular, with a <jats:italic>D<\/jats:italic>...<jats:italic>A<\/jats:italic> distance of 2.883\u2005(2)\u2005\u00c5 and a <jats:italic>D<\/jats:italic>\u2014H...<jats:italic>A<\/jats:italic> angle of 175.0\u2005(18)\u00b0 between the amide hydrogen atom and the P=O oxygen atom. These non-covalent interactions create ribbons that run along the <jats:italic>b<\/jats:italic>-axis direction.<\/jats:p>","DOI":"10.1107\/s205698901900820x","type":"journal-article","created":{"date-parts":[[2019,6,14]],"date-time":"2019-06-14T08:14:23Z","timestamp":1560500063000},"page":"991-996","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Crystal structures of two bis-carbamoylmethylphosphine oxide (CMPO) compounds"],"prefix":"10.1107","volume":"75","author":[{"given":"Andrew I.","family":"VanderWeide","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Richard J.","family":"Staples","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shannon M.","family":"Biros","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2019,6,14]]},"reference":[{"key":"pk2617_bb1","doi-asserted-by":"crossref","first-page":"10349","DOI":"10.1021\/ja0204269","volume":"124","author":"Amrhein","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"pk2617_bb2","doi-asserted-by":"crossref","first-page":"1175","DOI":"10.1039\/P29960001175","volume":"2","author":"Arnaud-Neu","year":"1996","journal-title":"J. Chem. Soc. Perkin Trans."},{"key":"pk2617_bb3","doi-asserted-by":"crossref","first-page":"1440","DOI":"10.1007\/s11172-006-0437-2","volume":"55","author":"Artyushin","year":"2006","journal-title":"Russ. Chem. Bull."},{"key":"pk2617_bb4","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1107\/S2053273314022207","volume":"71","author":"Bourhis","year":"2015","journal-title":"Acta Cryst. A"},{"unstructured":"Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.","key":"pk2617_bb5"},{"key":"pk2617_bb6","doi-asserted-by":"crossref","first-page":"367","DOI":"10.1039\/B603847F","volume":"36","author":"Dam","year":"2007","journal-title":"Chem. Soc. Rev."},{"key":"pk2617_bb7","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"pk2617_bb8","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"pk2617_bb13","doi-asserted-by":"crossref","first-page":"75","DOI":"10.1080\/07366298508918504","volume":"3","author":"Horwitz","year":"1985","journal-title":"Solvent Extr. Ion Exch."},{"key":"pk2617_bb9","doi-asserted-by":"crossref","first-page":"7229","DOI":"10.1039\/C7CS00574A","volume":"46","author":"Leoncini","year":"2017","journal-title":"Chem. Soc. Rev."},{"key":"pk2617_bb10","doi-asserted-by":"crossref","first-page":"1626","DOI":"10.1246\/cl.150861","volume":"44","author":"Miyazaki","year":"2015","journal-title":"Chem. Lett."},{"key":"pk2617_bb11","doi-asserted-by":"crossref","first-page":"8368","DOI":"10.1039\/C3DT53611D","volume":"43","author":"Ouizem","year":"2014","journal-title":"Dalton Trans."},{"unstructured":"Palmer, D. (2007). CrystalMaker. CrystalMaker Software, Bicester, England.","key":"pk2617_bb12"},{"key":"pk2617_bb14","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1070\/RC2014v083n02ABEH004384","volume":"83","author":"Sharova","year":"2014","journal-title":"Russ. Chem. Rev."},{"key":"pk2617_bb15","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Cryst. A"},{"key":"pk2617_bb16","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"pk2617_bb17","doi-asserted-by":"crossref","first-page":"188","DOI":"10.1107\/S1600536814020078","volume":"70","author":"Stoscup","year":"2014","journal-title":"Acta Cryst. E"},{"key":"pk2617_bb18","doi-asserted-by":"crossref","first-page":"2067","DOI":"10.1039\/C9QO00242A","volume":"6","author":"Werner","year":"2019","journal-title":"Org. Chem. Front."},{"key":"pk2617_bb19","doi-asserted-by":"crossref","first-page":"955","DOI":"10.1039\/B617136B","author":"Yang","year":"2007","journal-title":"Dalton Trans."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2019\/07\/00\/pk2617\/pk2617.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2019\/07\/00\/pk2617\/pk2617.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T10:44:58Z","timestamp":1736765098000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S205698901900820X"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,6,14]]},"references-count":19,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2019,7]]}},"alternative-id":["S205698901900820X"],"URL":"https:\/\/doi.org\/10.1107\/s205698901900820x","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S205698901900820X\/pk2617sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S205698901900820X\/pk2617Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S205698901900820X\/pk2617Isup4.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S205698901900820X\/pk2617IIsup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S205698901900820X\/pk2617IIsup5.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"type":"electronic","value":"2056-9890"}],"subject":[],"published":{"date-parts":[[2019,6,14]]},"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":"http:\/\/scripts.iucr.org\/cgi-bin\/citedin?pk2617","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 2019","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"6 June 2019","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"14 June 2019","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":"http:\/\/scripts.iucr.org\/cgi-bin\/sendsup?pk2617"}},{"value":"\u00a9 2019 VanderWeide 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"}}]}}