Acta Cryst. (2013). C69, 1181-1185 [ doi:10.1107/S010827011302341X ]
Abstract: The mixed-amide phosphinates, rac-phenyl (N-methylcyclohexylamido)(p-tolylamido)phosphinate, C20H27N2O2P, (I), and rac-phenyl (allylamido)(p-tolylamido)phosphinate, C16H19N2O2P, (II), were synthesized from the racemic phosphorus-chlorine compound (R,S)-(Cl)P(O)(OC6H5)(NHC6H4-p-CH3). Furthermore, the phosphorus-chlorine compound ClP(O)(OC6H5)(NH-cyclo-C6H11) was synthesized for the first time and used for the synthesis of rac-phenyl (benzylamido)(cyclohexylamido)phosphinate, C19H25N2O2P, (III). The strategies for the synthesis of racemic mixed-amide phosphinates are discussed. The P atom in each compound is in a distorted tetrahedral (N1)P(=O)(O)(N2) environment. In (I) and (II), the p-tolylamido substituent makes a longer P-N bond than those involving the N-methylcyclohexylamido and allylamido substituents. In (III), the differences between the P-N bond lengths involving the cyclohexylamido and benzylamido substituents are not significant. In all three structures, the phosphoryl O atom takes part with the N-H unit in hydrogen-bonding interactions, viz. an N-HO=P hydrogen bond for (I) and (N-H)(N-H)O=P hydrogen bonds for (II) and (III), building linear arrangements along  for (I) and along  for (III), and a ladder arrangement along  for (II).
Formula: C20H27N2O2P, C16H19N2O2P and C19H25N2O2P
Keywords: crystal structure; racemic mixed-amide phosphinates; P-N bonds; N-HO=P hydrogen bonds.
Structure factor file (CIF format) (141.2 kbytes)
Structure factor file (CIF format) (113.5 kbytes)
Structure factor file (CIF format) (129.9 kbytes)
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