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.
We present the synthesis and characterization of seven new phosphoric triamides followed by analysis of hydrogen bond patterns of the new compounds as well as the phosphoric triamides found in the Cambridge Structural Database (CSD). The analysis of hydrogen bond patterns updates the previous work (Toghraee, Pourayoubi and Divjakovic in Polyhedron, 2011, 30, 1680) on phosphoric triamides with a CIJO)NHPIJO)ijN] 2 skeleton, and extends the analysis to other phosphoric triamides i.e. ones without a CO attached to the N of N-PO. For the new phosphoric triamides we also investigated their spectroscopic features ( 31 P, 1 H, 13 C, and 15 N NMR, mass spectroscopy, IR spectroscopy), measured the 1 J( 15 N, 31 P) coupling constants and discussed the effective parameters.
Five new compounds belonging to the phosphoric triamide family have been synthesized: two of them with the formula XC(O)NHP(O)Y [X = CF3 (1) and CClF2 (2), Y = NHCH2C(CH3)2CH2NH] involving a 1,3-diazaphosphorinane ring part, and three 2,6-Cl2C6H3C(O)NHP(O)Z2 phosphoric triamides [Z = NHC(CH3)3 (3), N(CH3)(C6H11) (4) and N(CH3)(CH2C6H5) (5)]. The characterization was performed by (31)P{(1)H}, (1)H, (13)C NMR, IR spectroscopy besides (19)F NMR for fluorine containing compounds (1) and (2), and X-ray single-crystal structure analysis for (1), (3), (4) and (5). In each molecule the P atom has a distorted tetrahedral environment. The N atoms bonded to P atom have mainly sp(2) character with a very slight tendency to a pyramidal coordination for some amido groups. Different types of N-H···O hydrogen bonds have been analyzed for (1), (3), (4) and (5) and 118 other structures (including 194 hydrogen bonds) deposited in the Cambridge Structural Database, containing either C(O)-NH-P(O)[N(C)(C)]2 or C(O)-NH-P(O)[NH(C)]2. The participation of N(CP)-H···O=P [N(CP) = the nitrogen atom of the C(O)-NH-P(O) fragment], N-H···O=P, N-H···O=C and N(CP)-H···O=C hydrogen bonds in different hydrogen-bonded motifs are discussed. Moreover, the involvement of the O atoms of C=O or P=O in the [N(CP)-H][N-H]···O=P, [N-H]2···O=P, [N-H]2···O=C and [N-H]3···O=C groups are considered. A histogram of N···O distances, the distribution of N-H···O angles and the scatterplot of N-H···O angles versus N···O distances are studied.
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