Interplay Between Conformation and Hydrogen Bond Pattern: Crystal Structure of N-(2,2-dichloroacetyl)-N',N"-dipropylphosphoric Triamide and a Database Survey

The interplay between conformation and hydrogen bond pattern was studied in 211 (C(O)NH)(N) 2 P(O)-based phosphoric triamides retrieved from the Cambridge Structural Database (CSD) and one new molecular structure, (CHCl 2 C(O)NH)(CH 3 CH 2 CH 2 NH) 2 P(O). The O═C–N–P and C–N–P═O torsion angles were extracted for the conformational study of the C(O)NP(O) segment, and the conformations of ± sp ± ap , ± sp ± sc and ± ap ± sp were found ( sp = synperiplanar, ap = antiperiplanar, sc = synclinal). The conformations of hydrogen bond donor group(s) with respect to the acceptor group(s) were also considered. The investigated structures belong to three classes of (RC(O)NH)(R 1 R 2 N) 2 P(O) (R 1 and R 2 ≠ H), (RC(O)NH)(R 1 NH) 2 P(O) (R 1 ≠ H) and heterocyclic (RC(O)NH)P(O)[NR 1 ] 2 R 2 phosphoric triamides (R 1 = H or ≠ H, R 2 = a hydrocarbon fragment), and the hydrogen bond patterns include dimer, tetramer, chain, tape, ladder, two-dimensional assembly and three-dimensional architecture. In the new structure, the conformation of the C(O)NP(O) fragment is –sp+ap , and molecules are assembled in a tape arrangement (parallel to the [110] axis) through N CP –H···O═P and N P –H···O═C hydrogen bonds (N CP is the nitrogen atom of the C(O)NHP(O) fragment and N P is the other N atom bonded to phosphorus). Graphical Abstract The interplay between conformation and hydrogen bond pattern was studied in 211 (C(O)NH)(N) 2 P(O)-based phosphoric triamides retrieved from the Cambridge Structural Database (CSD) and one new structure, (CHCl 2 C(O)NH)(CH 3 CH 2 CH 2 NH) 2 P(O).