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The crystal structure of diphenyl (benzylcarbamothioyl)phosphoramide, (C 6 H 5 O) 2 P(O)(NHC(S)NHCH 2 C 6 H 5 ), is reported. In the P(O)NHC(S)NH moiety the conformations are − ap /+ ap /− sp , based on the O = P-N-C/P-N-C-N/P-N-C = S torsion angles ( ap  = antiperiplanar and  sp  = synperiplanar), which are different from the conformations of similar moiety in analogous structures retrieved from the Cambridge Structural Database (CSD). The calculated energies of the most stable seven conformers of the title compound (gas phase) are compared with the conformer found in the crystal structure, and the latter shows a relatively high energy value. In the crystal structure, a double-layered two-dimensional supramolecular assembly, along the  bc  plane, is mediated through (N-H···)(N-H···)O = P and π···π interactions, with cooperation from C-H···π, C-H···O and C-H···S. Energy framework calculations show the significant role of N-H···O hydrogen bonds in the  c  direction and the weak interactions with mainly dispersion component in the other two directions. The hydrogen bonds and weak interactions were confirmed by the quantum theory of atoms in molecules (AIM).

phosphorus, sulfur, and silicon and the related elements

A comparative conformational study of (C 6 H 5 O) 2 P(O)(NHC(S)NHCH 2 C 6 H 5 ) and analogous X-ray structures: energy calculations (solid-state/gas phase)