N-tert-Butyl O-2-isopropyl-5-methyl­cyclo­hexyl phenyl­phospho­namidate

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

doi:10.1107/S1600536811012864

. 2011 Apr 29;67(Pt 5):o1244. doi: 10.1107/S1600536811012864

N-tert-Butyl O-2-isopropyl-5-methylcyclohexyl phenylphosphonamidate

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

PMCID: PMC3089078 PMID: 21754537

Abstract

In the title compound, C₂₀H₃₄NO₂P, the P atom has an irregular tetrahedral environment and exhibits S _p chirality. In the crystal, weak intermolecular N—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains extending in [010].

Related literature

For the crystal structures of related P-chiral compounds, see: Chaloner et al. (1991 ▶); Meng et al. (2010 ▶).

Experimental

Crystal data

C₂₀H₃₄NO₂P
M _r = 351.45
Orthorhombic,
a = 8.305 (3) Å
b = 11.064 (4) Å
c = 22.557 (9) Å
V = 2072.8 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 298 K
0.45 × 0.40 × 0.37 mm

Data collection

Bruker SMART-1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.938, T _max = 0.949
10336 measured reflections
3610 independent reflections
1993 reflections with I > 2σ(I)
R _int = 0.075

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.130
S = 1.02
3610 reflections
223 parameters
114 restraints
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.31 e Å⁻³
Absolute structure: Flack (1983 ▶), 2085 Friedel pairs
Flack parameter: 0.06 (17)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536811012864/cv5071sup1.cif

e-67-o1244-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012864/cv5071Isup2.hkl

e-67-o1244-Isup2.hkl^{(177KB, 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	2.52	3.326 (4)	156
C13—H13⋯O2ⁱ	0.93	2.51	3.391 (5)	157

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Symmetry code: (i) Inline graphic .

Acknowledgments

We acknowledge financial support by the Natural Science Foundation of China (grant No. 20772055).

supplementary crystallographic information

Comment

We recently reported the crystal stucture of 2-isopropyl-5-methylcyclohexyl N-cyclohexyl-P- phenylphosphonamidate synthesized by the reaction of (R_p)-O-menthyl phenylphosphinate with cyclohexylamine (Meng et al., 2010). Herein we report the title compound (I) obtained by the reaction of the same phosphinate with tert-butylamine.

In (I) (Fig.1), the configuration of the central P atom was detemined as S and the four groups around the P atom form an irregular tetrahedron. A stable chair conformation was observed for the 2-isopropyl-5-methylcyclohexyloxy, in which the isopropyl, methyl and oxygen atom locate at equatorial bond. The absolute configuration of C₄, C₇, and C₁₁ are S, R, and R, respectively. The bond angle around the P atom are normal and comparable with those observed in the related compounds (Meng et al., 2010; Chaloner et al. 1991).

In the crystal structure, the molecules are linked by weak intermolecular N1—H1···O2 and C13—H13···O2 hodrogen bonds (Tabel 1) into chains extended in [010].

Experimental

Carbon tetrachloride was added to a solution of (R_p)-O-menthyl-phenylphosphonothioate dissolved in dry ether and tert-butylamine.The reaction mixture was stirred for 30 h at room temperature. The crystal suitable for X-ray diffraction was obtained by recrystallization with dichloromethane/hexane.