The P atom in the title compound, C19H29N4O4P, exhibits a tetra­hedral coordination and the phosphoryl and carbonyl groups are anti to each other. Adjacent mol­ecules are linked by N—H⋯O hydrogen bonds to form a layer motif.

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In the title compound, C14H30N3OP, both cyclo­hexyl groups adopt chair conformations with the NH unit in an equatorial position. The P atom adopts a slightly distorted tetra­hedral environment. In the (CH3)2NP(O) unit, the O—P—N—C torsion angles, showing the orientations of the methyl groups with respect to the phosphoryl group, are −166.6 (3) and 34.6 (4)°. The O atom of the P=O group acts as a double hydrogen-bond acceptor and is involved in two different inter­molecular N—H⋯OP hydrogen bonds, building R 2 2(8) rings that are further linked into chains running parallel to the b axis.

The crystal structures of two single-enantiomer amidophosphoesters with an (O) 2 P(O)(N) skeleton, i.e. diphenyl [(R)-(+)--methylbenzylamido]phosphate, (I), and diphenyl [(S)-(À)--methylbenzylamido]phosphate, (II), both C 20 H 20 -NO 3 P, are reported. In both structures, chiral one-dimensional hydrogenbonded architectures, along [010], are mediated by N-HÁ Á ÁOP interactions. The statistically identical assemblies include the noncentrosymmetric graph-set motif C(4) and the compounds crystallize in the chiral space group P2 1 . As a result of synergistic co-operation from C-HÁ Á ÁO interactions, a two-dimensional superstructure is built including a noncentrosymmetric R 4 4 (22) hydrogenbonded motif. A Cambridge Structural Database survey was performed on (O) 2 P(O)(N)-based structures in order to review the frequency of space groups observed in this family of compounds; the hydrogen-bond motifs in structures with chiral space groups and the types of groups inducing chirality are discussed. The 2,3 J X-P (X = H or C) coupling constants from the NMR spectra of (I) and (II) have been studied. In each compound, the two diastereotopic C 6 H 5 O groups are different, which is reflected in the different chemical shifts and some coupling constants.

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In the structure of 2-(4-chloroanilino)-1,3,2λ-diazaphosphol-2-one, CHClNOP, each molecule is connected with four neighbouring molecules through (N-H)...O hydrogen bonds. These hydrogen bonds form a tubular arrangement along the [001] direction built from R(12) and R(14) hydrogen-bond ring motifs, combined with a C(4) chain motif. The hole constructed in the tubular architecture includes a 12-atom arrangement (three P, three N, three O and three H atoms) belonging to three adjacent molecules hydrogen bonded to each other. One of the N-H groups of the diazaphosphole ring, not co-operating in classical hydrogen bonding, takes part in an N-H...π interaction. This interaction occurs within the tubular array and does not change the dimension of the hydrogen-bond pattern. The energies of the N-H...O and N-H...π hydrogen bonds were studied by NBO (natural bond orbital) analysis, using the experimental hydrogen-bonded cluster of molecules as the input file for the chemical calculations. In the H NMR experiment, the nitrogen-bound proton of the diazaphosphole ring has a high value of 17.2 Hz for theJ coupling constant.

In the title mol­ecule, C19H25N2O2P, the P atom is bonded in a distorted tetra­hedral environment. The dihedral angle between the two phenyl rings is 89.09 (8)°. The methyl H atoms are disordered over two sets of sites with equal occupancy. The O atom of the P=O group acts as a double hydrogen-bond acceptor of the type (N—H)2⋯(O=)P—, forming R 2 2(8) rings which are further linked into chains along [010].

Key indicators: single-crystal X-ray study; T = 150 K; mean (C-C) = 0.004 Å; R factor = 0.054; wR factor = 0.103; data-to-parameter ratio = 21.4.In the title compound, C 10 H 16 N + ÁC 12 H 15 F 3 N 2 O 3 P À , the two P-N distances are significantly different [1.740 (2) and 1.641 (2) Å ]. In the crystal structure, cations and anions are connected via intermolecular N-HÁ Á ÁO hydrogen bonds to form chains of centrosymmetric rings propagating in the b-axis direction. organic compounds o4318 # 2007 International Union of Crystallography