Phenyl bis­(morpholin-4-yl­amido)­phosphinate

Mehrdad Pourayoubi; Hossein Eshtiagh-Hosseini; Monireh Negari; Marek Nečas

doi:10.1107/S1600536811029734

. 2011 Jul 30;67(Pt 8):o2202. doi: 10.1107/S1600536811029734

Phenyl bis(morpholin-4-ylamido)phosphinate

Mehrdad Pourayoubi ^a,^*, Hossein Eshtiagh-Hosseini ^a, Monireh Negari ^a, Marek Nečas ^b

PMCID: PMC3213632 PMID: 22091209

Abstract

In the title compound, C₁₄H₂₃N₄O₄P, the P atom is in a distorted tetrahedral environment with bond angles in the range 96.87 (6)–119.86 (6)°. The two morpholinyl groups adopt a chair conformation. The phenyl ring is disordered over two sets of sites with equal occupancies [0.500 (2)]. In the crystal, adjacent molecules are linked via N—H⋯O hydrogen bonds into an extended chain running parallel to the a axis. Only one of the amidate N—H groups is involved in hydrogen bonding.

Related literature

For background to compounds having a P(=O)(O)(N)(N) skeleton, see: Sabbaghi et al. (2010 ▶). For bond lengths and angles in related structures, see: Ghadimi et al. (2009 ▶).

Experimental

Crystal data

C₁₄H₂₃N₄O₄P
M _r = 342.33
Triclinic,
a = 4.7469 (2) Å
b = 12.3528 (5) Å
c = 14.2149 (5) Å
α = 90.542 (3)°
β = 98.389 (4)°
γ = 93.009 (4)°
V = 823.35 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 120 K
0.20 × 0.10 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur S diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.877, T _max = 1.000
10043 measured reflections
2888 independent reflections
2272 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.029
wR(F ²) = 0.070
S = 0.99
2888 reflections
262 parameters
162 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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, global. DOI: 10.1107/S1600536811029734/gk2392sup1.cif

e-67-o2202-sup1.cif^{(26.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029734/gk2392Isup2.hkl

e-67-o2202-Isup2.hkl^{(141.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811029734/gk2392Isup3.cml

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
N3—H3N⋯O1ⁱ	0.823 (15)	2.093 (16)	2.8951 (16)	164.9 (15)

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Symmetry code: (i) Inline graphic .

Acknowledgments

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

supplementary crystallographic information

Comment

Structure determination of the title compound, P(O)[OC₆H₅][NHNC₄H₈O]₂ (Fig. 1), was performed as a part of a project in our laboratory on the synthesis of compounds having a P(═O)(O)(N)(N) skeleton (Sabbaghi et al., 2010). Single crystals of title compound were obtained from a mixture of CH₃OH/CH₃CN (4:1 v/v) after slow evaporation at room temperature.

The P═O (1.4705 (10) Å), P—O (1.5975 (10) Å) and P—N (1.6295 (13) Å & 1.6331 (13) Å) bond lengths and the C—O—P angle (122.17 (8)°) are standard for this category of compounds (Ghadimi et al., 2009). The P atom has a distorted tetrahedral configuration (Fig. 1), the bond angles at the P atom vary in the range from 96.87 (6)° [the angle O2—P1—N3] to 119.86 (6)° [the angle O1—P1—N3].

In the crystal, the molecules are hydrogen-bonded in a linear arrangement parallel to [100] through N3—H3N···O1ⁱ [symmetry code: (i) x - 1, y, z] hydrogen bond (Table 1, Fig. 2).

Experimental

To a solution of phenyldichlorophosphate (2.507 mmol) in chloroform (15 ml), a solution of aminomorpholine (10.028 mmol) in chloroform (30 ml) was added at 273 K. After 4 h of stirring, the solvent was evaporated in vacuum. The solid was washed with distilled water. Single crystals, suitable for crystallography, were obtained from a solution of the title compound in methanol and acetonitrile (4:1) after slow evaporation at room temperature. IR (KBr, cm^-1): 3278, 3107, 2945, 2869, 2830, 1588, 1488, 1223, 1107, 926, 869, 759, 698.