The P atom of the title compound, C20H21N2O2P, has a distorted tetrahedral configuration; the bond angles at P are in the range 96.11 (6)–117.32 (8)°. The N atom exhibits sp 2 character. In the crystal, molecules are connected via N—H⋯O hydrogen bonds into bands along the a axis, consisting of R 2 2(8) rings.
In the hydrogen-bond patterns of phenyl bis(2-chlorobenzylamido)phosphinate, C(20)H(19)Cl(2)N(2)O(2)P, (I), and N,N'-bis(2-chlorobenzyl)-N''-(2,2,2-trifluoroacetyl)phosphoric triamide, C(16)H(15)Cl(2)F(3)N(3)O(2)P, (II), the O atoms of the related phosphoryl groups act as double H-atom acceptors, so that the P=O···(H-N)(2) hydrogen bond in (I) and the P=O···(H-N(amide))(2) and C=O···H-N(C(O)NHP(O)) hydrogen bonds in (II) are responsible for the aggregation of the molecules in the crystal packing. The presence of a double H-atom acceptor centre is a result of the involvement of a greater number of H-atom donor sites with a smaller number of H-atom acceptor sites in the hydrogen-bonding interactions. This article also reviews structures having a P(O)NH group, with the aim of finding similar three-centre hydrogen bonds in the packing of phosphoramidate compounds. This analysis shows that the factors affecting the preference of the above-mentioned O atom to act as a double H-atom acceptor are: (i) a higher number of H-atom donor sites relative to H-atom acceptor centres in molecules with P(=O)(NH)(3), (N)P(=O)(NH)(2), C(=O)NHP(=O)(NH)(2) and (NH)(2)P(=O)OP(=O)(NH)(2) groups, and (ii) the remarkable H-atom acceptability of this atom relative to the other acceptor centre(s) in molecules containing an OP(=O)(NH)(2) group, with the explanation that the N atom bound to the P atom in almost all of the structures found does not take part in hydrogen bonding as an acceptor. Moreover, the differences in the H-atom acceptability of the phosphoryl O atom relative to the O atom of the alkoxy or phenoxy groups in amidophosphoric acid esters may be illustrated by considering the molecular packing of compounds having (O)(2)P(=O)(NH) and (O)P(=O)(NH)(N)groups, in which the unique N-H unit in the above-mentioned molecules almost always selects the phosphoryl O atom as a partner in forming hydrogen-bond interactions. The P atoms in (I) and (II) are in tetrahedral coordination environments, and the phosphoryl and carbonyl groups in (II) are anti with respect to each other (the P and C groups are separated by one N atom). In the crystal structures of (I) and (II), adjacent molecules are linked via the above-mentioned hydrogen bonds into a linear arrangement parallel to [100] in both cases, in (I) by forming R(2)(2)(8) rings and in (II) through a combination of R(2)(2)(10) and R(2)(1)(6) rings.
In the new tin(IV) and copper(II) complexes, cis-dichlorido-trans-dimethyl-cis-bis(N,N',N''-tricyclohexylphosphoric triamide-κO)tin(IV), [Sn(CH(3))(2)Cl(2)(C(18)H(36)N(3)OP)(2)], (I), and trans-diaquabis(N,N',N''-tricyclohexylphosphoric triamide-κO)copper(II) dinitrate-N,N',N''-tricyclohexylphosphoric triamide (1/2), [Cu(C(18)H(36)N(3)OP)(2)(H(2)O)(2)](NO(3))(2)·2C(18)H(36)N(3)OP, (II), the N,N',N''-tricyclohexylphosphoric triamide (PTA) ligands exist as hydrogen-bonded dimers via P=O···H-N interactions around the metal center. The asymmetric unit in (I) consists of one complete complex molecule located on a general position. The Sn(IV) coordination geometry is octahedral with two cis hydrogen-bonded PTA ligands, two cis chloride ligands and two trans methyl groups. The asymmetric unit in (II) contains one half of a [Cu(PTA)(2)(H(2)O)(2)](2+) dication on a special position (site symmetry ̅1 for the Cu atom), one nitrate anion and one free PTA molecule, both on general positions. The complex adopts a square-planar trans-[CuO(2)O(2)] coordination geometry, with the Cu(II) ion coordinated by two PTA ligands and two water molecules. Each of the noncoordinated PTA molecules is hydrogen bonded to a neighboring coordinated PTA molecule and an adjacent water molecule; the phosphoryl O atom acts as a double-H-atom acceptor. The P atoms in the PTA ligands of both complexes and in the noncoordinated hydrogen-bonded molecules in (II) adopt a slightly distorted tetrahedral environment.
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.
In the title salt, C10H16N+·Cl−, the cations and anions are linked by two N—H⋯Cl hydrogen bonds, forming a centrosymmetric tetramer.
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