Diphenyl [(S)-1-phenylpropanamido]phosphate

Abstract

The title compound, C21H22NO3P, was synthesized from the reaction of (C6H5O)2P(O)(Cl) and S-1-phenyl­propyl­amine (1:2 mole ratio) at 273 K, followed by removal of the S-1-phenyl­propyl­amine hydro­chloride by-product by dissolving in H2O. The P atom is located in a distorted tetra­hedral environment. The bond angles at the P atom vary from 99.51 (12) to 116.68 (12)°. The sp 2 character of the N atom is reflected by the C—N—P angle [120.9 (2)°]. The P=O group and the N—H unit adopt an anti orientation with respect to one another. In the crystal, adjacent mol­ecules are linked via N—H⋯O(P) hydrogen bonds into a one-dimensional arrangement running parallel to the a axis.

Analysis of N—H...O hydrogen bonds in new C(O)—NH—P(O)-based phosphoric triamides and analogous structures deposited in the Cambridge Structural Database

“…The N-HÁ Á ÁO P hydrogen bond was studied in the crystal packing of different families of phosphorus(V)-nitrogen compounds: phosphoric triamides (Chivers et al, 2003;Gholivand & Mahzouni, 2011;Gholivand et al, 2010Gholivand et al, , 2009, amido phosphonates (Sabbaghi et al, 2011), amido phosphinates (Pourayoubi, Eshtiagh-Hosseini et al, 2011), and cyclic oxazaphospholidines and oxazaphosphinanes (van der Lee et al, 2008). In this context, only a few studies have been devoted to the classification of hydrogen-bond patterns in the compounds having a C(O)-NH-P(O) fragment based on gauche or anti conformations of P O versus C O (Toghraee et al, 2011) and in compounds with an (O)P(O)(NH) 2 fragment (Pourayoubi, Nečas & Negari, 2012).…”