{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,18]],"date-time":"2026-03-18T07:28:40Z","timestamp":1773818920218,"version":"3.50.1"},"reference-count":18,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2013,9,6]],"date-time":"2013-09-06T00:00:00Z","timestamp":1378425600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2013,9,6]],"date-time":"2013-09-06T00:00:00Z","timestamp":1378425600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst Sect C","Acta Crystallogr C","Acta Crystallogr Sect C","Acta Crystallogr Sect C Cryst Struct Commun"],"published-print":{"date-parts":[[2013,10,1]]},"abstract":"<jats:p>The mixed-amide phosphinates,<jats:italic>rac<\/jats:italic>-phenyl (<jats:italic>N<\/jats:italic>-methylcyclohexylamido)(<jats:italic>p<\/jats:italic>-tolylamido)phosphinate, C<jats:sub>20<\/jats:sub>H<jats:sub>27<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>P, (I), and<jats:italic>rac<\/jats:italic>-phenyl (allylamido)(<jats:italic>p<\/jats:italic>-tolylamido)phosphinate, C<jats:sub>16<\/jats:sub>H<jats:sub>19<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>P, (II), were synthesized from the racemic phosphorus\u2013chlorine compound (<jats:italic>R<\/jats:italic>,<jats:italic>S<\/jats:italic>)-(Cl)P(O)(OC<jats:sub>6<\/jats:sub>H<jats:sub>5<\/jats:sub>)(NHC<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>-<jats:italic>p<\/jats:italic>-CH<jats:sub>3<\/jats:sub>). Furthermore, the phosphorus\u2013chlorine compound ClP(O)(OC<jats:sub>6<\/jats:sub>H<jats:sub>5<\/jats:sub>)(NH-<jats:italic>cyclo<\/jats:italic>-C<jats:sub>6<\/jats:sub>H<jats:sub>11<\/jats:sub>) was synthesized for the first time and used for the synthesis of<jats:italic>rac<\/jats:italic>-phenyl (benzylamido)(cyclohexylamido)phosphinate, C<jats:sub>19<\/jats:sub>H<jats:sub>25<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>2<\/jats:sub>P, (III). The strategies for the synthesis of racemic mixed-amide phosphinates are discussed. The P atom in each compound is in a distorted tetrahedral (N<jats:sup>1<\/jats:sup>)P(=O)(O)(N<jats:sup>2<\/jats:sup>) environment. In (I) and (II), the<jats:italic>p<\/jats:italic>-tolylamido substituent makes a longer P\u2014N bond than those involving the<jats:italic>N<\/jats:italic>-methylcyclohexylamido and allylamido substituents. In (III), the differences between the P\u2014N bond lengths involving the cyclohexylamido and benzylamido substituents are not significant. In all three structures, the phosphoryl O atom takes part with the N\u2014H unit in hydrogen-bonding interactions,<jats:italic>viz.<\/jats:italic>an N\u2014H...O=P hydrogen bond for (I) and (N\u2014H)(N\u2014H)...O=P hydrogen bonds for (II) and (III), building linear arrangements along [001] for (I) and along [010] for (III), and a ladder arrangement along [100] for (II).<\/jats:p>","DOI":"10.1107\/s010827011302341x","type":"journal-article","created":{"date-parts":[[2013,9,5]],"date-time":"2013-09-05T15:44:40Z","timestamp":1378395880000},"page":"1181-1185","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":4,"title":["New<i>rac<\/i>-<i>X<\/i>P(O)(OC<sub>6<\/sub>H<sub>5<\/sub>)(NHC<sub>6<\/sub>H<sub>4<\/sub>-<i>p<\/i>-CH<sub>3<\/sub>) [<i>X<\/i>= N(CH<sub>3<\/sub>)(<i>cyclo<\/i>-C<sub>6<\/sub>H<sub>11<\/sub>) and NH(C<sub>3<\/sub>H<sub>5<\/sub>)] and<i>rac<\/i>-(C<sub>6<\/sub>H<sub>5<\/sub>CH<sub>2<\/sub>NH)P(O)(OC<sub>6<\/sub>H<sub>5<\/sub>)(NH-<i>cyclo<\/i>-C<sub>6<\/sub>H<sub>11<\/sub>) mixed-amide phosphinates"],"prefix":"10.1107","volume":"69","author":[{"given":"Mehrdad","family":"Pourayoubi","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fatemeh","family":"Karimi Ahmadabad","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hossein","family":"Eshtiagh-Hosseini","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Monika","family":"Ku\u010der\u00e1kov\u00e1","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"V\u00e1clav","family":"Eigner","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michal","family":"Du\u0161ek","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2013,9,6]]},"reference":[{"key":"lg3117_bb1","unstructured":"Agilent (2013). 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