Diphenyl (cyclo­pentyl­amido)­phospho­nate

Fahimeh Sabbaghi; Mehrdad Pourayoubi; Poorya Zargaran; Giuseppe Bruno; Hadi Amiri Rudbari

doi:10.1107/S1600536811017028

. 2011 May 11;67(Pt 6):o1378. doi: 10.1107/S1600536811017028

Diphenyl (cyclopentylamido)phosphonate

Fahimeh Sabbaghi ^a,^*, Mehrdad Pourayoubi ^b, Poorya Zargaran ^b, Giuseppe Bruno ^c, Hadi Amiri Rudbari ^c

PMCID: PMC3120324 PMID: 21754768

Abstract

In the title molecule, C₁₇H₂₀NO₃P, the P atom is bonded in a distorted tetrahedral environment. The dihedral angle between the two phenyl rings is 23.52 (10)°. The phosphoryl and N—H groups are anti with respect to one another. The –CH₂–CH₂–CH₂–CH₂– sequence of atoms in the cyclopentyl ring is disordered over two sets of sites with refined occupancies of 0.574 (10) and 0.426 (10). In the crystal, molecules are linked via N—H⋯O=P hydrogen bonds to form extended chains along [010].

Related literature

For a related structure, see: Pourayoubi et al. (2011 ▶).

Experimental

Crystal data

C₁₇H₂₀NO₃P
M _r = 317.31
Monoclinic,
a = 18.0095 (4) Å
b = 5.3471 (1) Å
c = 17.9387 (4) Å
β = 109.731 (1)°
V = 1626.05 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 296 K
0.5 × 0.4 × 0.2 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.709, T _max = 0.747
139394 measured reflections
3531 independent reflections
3180 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.110
S = 1.08
3531 reflections
240 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008 ▶) and enCIFer (Allen et al., 2004 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017028/lh5228sup1.cif

e-67-o1378-sup1.cif^{(21.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017028/lh5228Isup2.hkl

e-67-o1378-Isup2.hkl^{(169.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811017028/lh5228Isup3.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
N—H⋯O1ⁱ	0.790 (19)	2.23 (2)	3.0039 (17)	167.7 (19)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

We have already studied the crystal structure of a diphenyl(amido)phosphonate, (C₆H₅O)₂P(O)(NHCH₂(2-ClC₆H₄) (Pourayoubi et al., 2011). Here, we report the synthesis and crystal structure of title compound.

The P═O, P—O and P—N bond lengths are standard for (amido)phosphonate compounds. The P atom has a distorted tetrahedral configuration (Fig. 1) with the bond angles in the range of 99.72 (6)° [O2–P–O3] to 115.93 (6)° [O1–P–O2]. The phosphoryl group and the N–H unit are in an anti orientation with respect to each other which allows adjacent molecules to form extended chains along [010] via N—H···O(P) hydrogen bonds (Table 1).

Experimental

To a solution of (C₆H₅O)₂P(O)Cl in chloroform, a solution of cyclopentylamine (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. Single crystals were obtained from a solution of the title compound in CH₃OH after slow evaporation at room temperature.