Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 10 (October 2013)

organic compounds

Acta Cryst. (2013). C69, 1181-1185    [ doi:10.1107/S010827011302341X ]

New rac-XP(O)(OC6H5)(NHC6H4-p-CH3) [X = N(CH3)(cyclo-C6H11) and NH(C3H5)] and rac-(C6H5CH2NH)P(O)(OC6H5)(NH-cyclo-C6H11) mixed-amide phosphinates

M. Pourayoubi, F. Karimi Ahmadabad, H. Eshtiagh-Hosseini, M. Kuceráková, V. Eigner and M. Dusek

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-H...O=P hydrogen bond for (I) and (N-H)(N-H)...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).

Formula: C20H27N2O2P, C16H19N2O2P and C19H25N2O2P

Keywords: crystal structure; racemic mixed-amide phosphinates; P-N bonds; N-H...O=P hydrogen bonds.

hkldisplay filedownload file

Structure factor file (CIF format) (141.2 kbytes)
[ doi:10.1107/S010827011302341X/lg3117Isup2.hkl ]
Contains datablock I

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Structure factor file (CIF format) (113.5 kbytes)
[ doi:10.1107/S010827011302341X/lg3117IIsup3.hkl ]
Contains datablock II

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Structure factor file (CIF format) (129.9 kbytes)
[ doi:10.1107/S010827011302341X/lg3117IIIsup4.hkl ]
Contains datablock III


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