Diphenyl (o-tolyl­amido)­phospho­nate

Fahimeh Sabbaghi; Mehrdad Pourayoubi; Poorya Zargaran

doi:10.1107/S1600536811013924

. 2011 Apr 16;67(Pt 5):o1170. doi: 10.1107/S1600536811013924

Diphenyl (o-tolylamido)phosphonate

Fahimeh Sabbaghi ^a,^*, Mehrdad Pourayoubi ^b, Poorya Zargaran ^b

PMCID: PMC3089329 PMID: 21754476

Abstract

The asymmetric unit of the title compound, C₁₉H₁₈NO₃P, contains two independent molecules in which the P atoms are found in slightly distorted tetrahedral environments. In the crystal, pairs of intermolecular N—H⋯O(P) hydrogen bonds form two independent centrosymmetric dimers.

Related literature

For a related structure, see: Pourayoubi et al. (2010 ▶).

Experimental

Crystal data

C₁₉H₁₈NO₃P
M _r = 339.31
Triclinic,
a = 10.2986 (13) Å
b = 10.3540 (12) Å
c = 17.993 (2) Å
α = 86.650 (2)°
β = 84.036 (2)°
γ = 62.429 (2)°
V = 1691.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 120 K
0.50 × 0.40 × 0.25 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T _min = 0.918, T _max = 0.956
17593 measured reflections
8135 independent reflections
6772 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.104
S = 1.00
8135 reflections
441 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL and enCIFer (Allen et al., 2004 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013924/lh5229sup1.cif

e-67-o1170-sup1.cif^{(28.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013924/lh5229Isup2.hkl

e-67-o1170-Isup2.hkl^{(397.9KB, 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—H1N⋯O1ⁱ	0.85 (2)	2.09 (2)	2.903 (1)	162 (1)
N1′—H1′N⋯O1′ⁱⁱ	0.86 (2)	2.02 (2)	2.867 (1)	167 (1)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

In previous work, the structure of diphenyl (p-tolylamido)phosphate was reported (Pourayoubi et al., 2010). Here, we report on the synthesis and crystal structure of title compound.

The asymmetric unit (Fig. 1) consists of two independent molecules. The P═O, P—O and P—N bond lengths are standard for amidophosphoric acid ester compounds (Pourayoubi et al., 2010). The P atoms of two independent molecules are in slightly distorted tetrahedral environments.

In each molecule, the phosphoryl group and the N-H unit are in a syn orientation with respect to each other and in the crystal, pairs of intermolecular N—H···O(P) hydrogen bonds (Table 1) form two independent centrosymmetric dimers (Fig. 2).

Experimental

To a solution of (C₆H₅O)₂P(O)Cl in chloroform, a solution of ortho-toluidine (1:2 mole ratio) in chloroform was added at 273 K. After 4 h stirring, the solvent was removed and product was washed with distilled water. Colorless plates were obtained by slow evaporation of a methanol solution of the title compound at room temperature.