2-Isopropyl-5-methyl­cyclo­hexyl N-cyclo­hexyl-P-phenyl­phospho­namidate

Fan-Jie Meng; Hao Xu; Li-Juan Liu; Daqi Wang; Chang-Qiu Zhao

doi:10.1107/S1600536810032319

. 2010 Aug 18;66(Pt 9):o2352. doi: 10.1107/S1600536810032319

2-Isopropyl-5-methylcyclohexyl N-cyclohexyl-P-phenylphosphonamidate

Fan-Jie Meng ^a, Hao Xu ^a, Li-Juan Liu ^a, Daqi Wang ^a, Chang-Qiu Zhao ^a,^*

PMCID: PMC3007901 PMID: 21588695

Abstract

The title compound, C₂₂H₃₆NO₂P, features a P atom bonded to a phenyl ring, a cyclohexylamine unit and the O atom of a menthyl group. In the crystal structure, intermolecular N—H⋯O hydrogen bonds connect molecules into a one-dimensional chain in the b direction.

Related literature

For the general synthesis of phosphorus–amine compounds, see: Steinberg (1950 ▶); Benamer et al. (2010 ▶). For the structures of related phosphorus–amine compounds, see: Balakrishna et al. (2001 ▶).

Experimental

Crystal data

C₂₂H₃₆NO₂P
M _r = 377.49
Orthorhombic,
a = 10.0205 (10) Å
b = 10.4317 (11) Å
c = 22.101 (2) Å
V = 2310.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 298 K
0.40 × 0.14 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.949, T _max = 0.991
11780 measured reflections
4064 independent reflections
2537 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.083
S = 1.00
4064 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 1727 Friedel pairs
Flack parameter: −0.01 (11)

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032319/vm2032sup1.cif

e-66-o2352-sup1.cif^{(23KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032319/vm2032Isup2.hkl

e-66-o2352-Isup2.hkl^{(199.2KB, 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⋯O2ⁱ	0.86	2.15	2.969 (3)	160

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the financial support of the Natural Science Foundation of China (grant No. 20772055).

supplementary crystallographic information

Comment

The molecular structure of the P-chiral title compound consists of an O-menthyl phenylphosphinate core and cyclohexylamine (Steinberg, 1950). The absolute configuration of the central P atom is S and the four groups around the central P atom form an irregular tetrahedron (Benamer et al., 2010). In the crystal structure intermolecular N—H···O hydrogen bonds connect molecules into a one-dimensional chain in the b-direction (Table 1, Fig. 2).

Experimental

Carbon tetrachloride was added to a solution of (R_p)-O-menthyl-phenyl phosphonothioate dissolved in dry ether and cyclohexylamine. The reaction mixture was stirred for 38 h at room temperature. A single crystal of the title compound suitable for X-ray diffraction was obtained by slow evaporation of an ether solution of the title compound.