Diphenyl [(S)-1-phenylpropanamido]­phosphate

Fahimeh Sabbaghi; Mehrdad Pourayoubi; Monireh Negari; Marek Nečas

doi:10.1107/S1600536811034507

. 2011 Aug 27;67(Pt 9):o2512. doi: 10.1107/S1600536811034507

Diphenyl [(S)-1-phenylpropanamido]phosphate

Fahimeh Sabbaghi ^a,^*, Mehrdad Pourayoubi ^b, Monireh Negari ^b, Marek Nečas ^c

PMCID: PMC3200690 PMID: 22064755

Abstract

The title compound, C₂₁H₂₂NO₃P, was synthesized from the reaction of (C₆H₅O)₂P(O)(Cl) and S-1-phenylpropylamine (1:2 mole ratio) at 273 K, followed by removal of the S-1-phenylpropylamine hydrochloride by-product by dissolving in H₂O. The P atom is located in a distorted tetrahedral environment. The bond angles at the P atom vary from 99.51 (12) to 116.68 (12)°. The sp ² character of the N atom is reflected by the C—N—P angle [120.9 (2)°]. The P=O group and the N—H unit adopt an anti orientation with respect to one another. In the crystal, adjacent molecules are linked via N—H⋯O(P) hydrogen bonds into a one-dimensional arrangement running parallel to the a axis.

Related literature

For background literature on phosphoramidates having a C(=O)NHP(=O) skeleton, and the hydrogen-bond patterns and strengths, see: Toghraee et al. (2011 ▶); Pourayoubi et al. (2011 ▶). For a related phosphoramidate with a P(=O)(O)₂(N) skeleton, and its bond lengths and angles, see: Pourayoubi et al. (2010 ▶).

Experimental

Crystal data

C₂₁H₂₂NO₃P
M _r = 367.37
Orthorhombic,
a = 5.4853 (3) Å
b = 8.1450 (11) Å
c = 41.162 (4) Å
V = 1839.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 120 K
0.40 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.981, T _max = 1.000
4914 measured reflections
3000 independent reflections
2404 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.089
S = 1.07
3000 reflections
239 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.42 e Å⁻³
Absolute structure: Flack (1983 ▶), 1052 Friedel pairs
Flack parameter: −0.09 (14)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536811034507/dn2713sup1.cif

e-67-o2512-sup1.cif^{(25.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034507/dn2713Isup2.hkl

e-67-o2512-Isup2.hkl^{(147.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.84 (1)	2.25 (1)	3.077 (3)	167 (3)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

Support of this investigation by Islamic Azad University, Zanjan Branch, and Ferdowsi University of Mashhad is gratefully acknowledged.

supplementary crystallographic information

Comment

In recently published papers concerning phosphoramidate compounds having a C(═O)NHP(═O)(N)₂ skeleton, the hydrogen bonds pattern (Toghraee et al., 2011) and strengths (Pourayoubi et al., 2011) were analyzed. In our continuing interest, we collected the structural data related to a new compound with a P(═O)(O)₂(N) skeleton belonging to the phosphoramide family.

The molecular structure of the title compound is given in Fig. 1. The P═O, P—O and P—N bond lengths and the C—N—P and C—O—P angles are standard for this category of phosphoramidate compounds (Pourayoubi et al., 2010).

In the crystal structure, molecules are linked via N—H···O(P) hydrogen bonds into extended chains running parallel to the a axis (Table 1, Fig. 2).

Experimental

To a solution of (C₆H₅O)₂P(O)Cl in chloroform, a solution of S-1-phenylpropylamine (1:2 mole ratio) in chloroform was added at 273 K. After 4 h of stirring, the solvent was removed and the obtained solid was washed with distilled water. Single crystals were obtained from a solution of the title compound in CHCl₃/n-C₇H₁₆ after slow evaporation at room temperature.