2-Isopropyl-5-methyl­cyclo­hexyl cyclo­hex­yl(phen­yl)phosphinate

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

doi:10.1107/S1600536811010592

. 2011 Mar 31;67(Pt 4):o991. doi: 10.1107/S1600536811010592

2-Isopropyl-5-methylcyclohexyl cyclohexyl(phenyl)phosphinate

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

PMCID: PMC3099872 PMID: 21754248

Abstract

In the title molecule, C₂₂H₃₅O₂P, the two cyclohexyl rings exhibit chair conformations. In the crystal, molecules related by translation along the b axis are linked by the weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the crystal structure of a related P-chiral compound, see: Fu & Zhao (2010 ▶).

Experimental

Crystal data

C₂₂H₃₅O₂P
M _r = 362.47
Monoclinic,
a = 11.4892 (13) Å
b = 5.8872 (6) Å
c = 16.3531 (17) Å
β = 94.696 (1)°
V = 1102.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 298 K
0.45 × 0.11 × 0.08 mm

Data collection

Bruker SMART-1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.941, T _max = 0.989
5833 measured reflections
3646 independent reflections
2125 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.119
S = 0.92
3646 reflections
229 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ▶), 1493 Friedel pairs
Flack parameter: 0.19 (14)

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/S1600536811010592/cv5058sup1.cif

e-67-0o991-sup1.cif^{(22.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010592/cv5058Isup2.hkl

e-67-0o991-Isup2.hkl^{(178.7KB, 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
C21—H21A⋯O2ⁱ	0.97	2.54	3.376 (5)	145
C17—H17⋯O2ⁱ	0.98	2.47	3.346 (5)	149

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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

In continuation of our study of phenylphosphinates (Fu & Zhao, 2010), we present here the title compound (I) prepared from substitution of O-menthyl phenylphosphoryl chloride with cyclohexyl magnesium chloride.

In (I) (Fig. 1), the configuration of phosphorus atom was determined as R. The compound is comprised of fully extended substituents: cyclohexyl, menthyoxy and phenyl, which form an irregular tetrahedron. The geometric parameters of (I) are usual. The bond angle of C17—P—C11 is 108.65 (18)°, O1—P—C11 is 105.37 (15)°, O1—P—C17 is 102.47 (15)°, O2—P—O1 is 113.94 (16)°, O2—P—C17 is 115.03 (18)° and O2—P—C11 is 110.65 (18) °.

In the crystal structure, the molecules related by translation along b axis are linked by the weak intermolecular C—H···O hydrogen bonds (Table 1) into chains.

Experimental

O-Menthyl phenylphosphoryl chloride (0.3 mmol) was added to a stirred ether solution of cyclohexyl magnesium chloride (0.6 mmol) under nitrogen and the mixture was stirred for 24 h at room temperature. After washing with water, the resulting solution was purified by preparative TLC on silica gel to afford optically pure product. The crystal suitable for X-ray diffraction was obtained from recrystallization with ethyl ether/hexane.