Research Article: N,N′-Dibenzyl-N′′-(2,4-difluoro­benzo­yl)-N,N′-dimethyl­phospho­ric triamide

Date Published: February 01, 2012

Publisher: International Union of Crystallography

Author(s): Mehrdad Pourayoubi, Samad Shoghpour, Laura Torre-Fernández, Santiago García-Granda.


In the title mol­ecule, C23H24F2N3O2P, the P atom is in a distorted tetra­hedral P(=O)(N)(N)2 environment, with the bond angles around the P atom in the range 106.78 (11)–114.10 (13)°. The phosphoryl and carbonyl groups, which are separated by an N atom, adopt an anti orientation relative to each other. In the C(=O)NHP(=O) fragment, the P—N bond is longer [1.683 (2) Å] and the O—P—N angle is smaller [106.78 (11)°] than the other P—N bonds [1.613 (2) and 1.632 (2) Å] and O—P—N bond angles [114.10 (13) and 110.83 (12)°], respectively. The N atoms have sp2 character. In the crystal, pairs of P=O⋯H—N hydrogen bonds form inversion dimers with R22(8) ring motifs.

Partial Text

For hydrogen-bond patterns in compounds with formula RC(O)NHP(O)[NR1R2]2 and RC(O)NHP(O)[NHR1]2 and for the discussion of different C(=O) versus P(=O) orientations in the C(O)NHP(O) fragment, see: Toghraee et al. (2011 ▶). For hydrogen-bond strengths in cyclic hydrogen-bond motifs and for bond lengths and angles, see: Pourayoubi et al. (2011 ▶). For graph-set analysis of hydrogen-bonds motifs, see: Bernstein et al. (1995 ▶). For the synthesis of the starting phospho­rous–chlorine compound, see: Pourayoubi et al. (2010 ▶).