p-Tolyl bis­(o-tolyl­amido)­phosphinate

Fahimeh Sabbaghi; Teresa Mancilla Percino; Mehrdad Pourayoubi; Marco A Leyva

doi:10.1107/S1600536810023512

. 2010 Jun 23;66(Pt 7):o1755. doi: 10.1107/S1600536810023512

p-Tolyl bis(o-tolylamido)phosphinate

Fahimeh Sabbaghi ^a,^*, Teresa Mancilla Percino ^b, Mehrdad Pourayoubi ^c, Marco A Leyva ^b

PMCID: PMC3006771 PMID: 21587971

Abstract

In the title compound, C₂₁H₂₃N₂O₂P, the P atom has a distorted tetrahedral configuration. The O atom of the OC₆H₄-4-CH₃ group and the N atoms show sp ² character. In the crystal, adjacent molecules are linked by N—H⋯O hydrogen bonds into helical chains parallel to the b axis.

Related literature

For a related structure, see: Pourayoubi et al. (2009 ▶).

Experimental

Crystal data

C₂₁H₂₃N₂O₂P
M _r = 366.38
Monoclinic,
a = 12.157 (3) Å
b = 8.978 (2) Å
c = 18.080 (5) Å
β = 101.569 (1)°
V = 1933.3 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.6 × 0.54 × 0.47 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (Blessing, 1995 ▶) T _min = 0.860, T _max = 0.968
23372 measured reflections
4402 independent reflections
3097 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.128
S = 1.06
4402 reflections
257 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: HKL DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023512/ng2779sup1.cif

e-66-o1755-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023512/ng2779Isup2.hkl

e-66-o1755-Isup2.hkl^{(211.3KB, 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⋯O1ⁱ	0.91 (2)	2.02 (2)	2.8963 (19)	161 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

In the previous work, the structure determination of p-tolyl bis(p-tolylamido)phosphate (Pourayoubi et al., 2009) has been investigated; we report here on the crystal structure of title compound (Fig. 1). The title compound was synthesized from the reaction of (4-tolyl)-dichlorophosphate with an excess amount of ortho-toluidine (1:4 mole ratio). Single crystals were obtained from CHCl₃/n-C₆H₁₄ at room temperature. Molecular structure of [4-H₃C—C₆H₄O]P(O)[NHC₆H₄-2-CH₃]₂ is shown in Fig. 1. The phosphorus atom has a distorted tetrahedral configuration. The bond angles around P atom are in the range of 96.87 (7)° to 118.95 (8)°. The oxygen atom of OC₆H₄-4-CH₃ moiety and the nitrogen atoms show sp² character (the C15—O2—P1 angle is 124.67 (11)°, the C1—N1—P1 and C8—N2—P1 are 123.77 (12)° and 127.71 (12)°, respectively. In the crystal structure, molecules are linked via N—H···O hydrogen bonds (N1···O1 = 2.8963 (19) Å) into an extended chain (Fig. 2) parallel to the b axis.

Experimental

To a solution of (4-tolyl)-dichlorophosphate (2.250 g, 10 mmol) in 15 ml dry acetonitrile, a solution of ortho-toluidine (4.286 g, 40 mmol) in 30 ml acetonitrile was added at 0°C. After 4 h stirring, the solvent was evaporated in vacuum. The solid was washed with distilled water. Single crystals of the product were obtained from a solution of CHCl₃/n-C₆H₁₄ at room temperature.