Crystal structures of two bis-carbamoyl-methyl-phosphine oxide (CMPO) compounds.

ABSTRACT: Two bis-carbamoyl-methyl-phosphine oxide compounds, namely {[(3-{[2-(di-phen-yl-phosphino-yl)ethanamido]-meth-yl}benz-yl)carbamo-yl]meth-yl}di-phenyl-phos-phine oxide, C₃₆H₃₄N₂O₄P₂, (I), and diethyl [({2-[2-(di-eth-oxy-phosphino-yl)ethanamido]-eth-yl}carbamo-yl)meth-yl]phospho-nate, C₁₄H₃₀N₂O₈P₂, (II), were synthesized via nucleophilic acyl substitution reactions between an ester and a primary amine. Hydrogen-bonding inter-actions are present in both crystals, but these inter-actions are intra-molecular in the case of compound (I) and inter-molecular in compound (II). Intra-molecular ?-? stacking inter-actions are also present in the crystal of compound (I) with a centroid-centroid distance of 3.9479?(12)?Å and a dihedral angle of 9.56?(12)°. Inter-molecular C-H?? inter-actions [C?centroid distance of 3.622?(2)?Å, C-H?centroid angle of 146°] give rise to supra-molecular sheets that lie in the ab plane. Key geometric features for compound (I) involve a nearly planar, trans-amide group with a C-N-C-C torsion angle of 169.12?(17)°, and a torsion angle of -108.39?(15)° between the phosphine oxide phospho-rus atom and the amide nitro-gen atom. For compound (II), the electron density corresponding to the phosphoryl group was disordered, and was modeled as two parts with a 0.7387?(19):0.2613?(19) occupancy ratio. Compound (II) also boasts a trans-amide group that approaches planarity with a C-N-C-C torsion angle of -176.50?(16)°. The hydrogen bonds in this structure are inter-molecular, with a D?A distance of 2.883?(2)?Å and a D-H?A angle of 175.0?(18)° between the amide hydrogen atom and the P=O oxygen atom. These non-covalent inter-actions create ribbons that run along the b-axis direction.

SUBMITTER: VanderWeide AI 

PROVIDER: S-EPMC6659340 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature