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

Xu, H.; Liu, L.-J.; Meng, F.-J.; Zhao, C.-Q.

doi:10.1107/S1600536811010592

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o991

doi:10.1107/S1600536811010592

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

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

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: literabc@hotmail.com

(Received 2 March 2011; accepted 22 March 2011; online 31 March 2011)

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, P 2₁
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[F² > 2σ(F²)] = 0.053
wR(F²) = 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)

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
Symmetry code: (i) x, y-1, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010592/cv5058sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

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

Crystal data top

C₂₂H₃₅O₂P	F(000) = 396
M_r = 362.47	D_x = 1.092 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1233 reflections
a = 11.4892 (13) Å	θ = 2.5–26.0°
b = 5.8872 (6) Å	µ = 0.14 mm⁻¹
c = 16.3531 (17) Å	T = 298 K
β = 94.696 (1)°	Block, colourless
V = 1102.4 (2) Å³	0.45 × 0.11 × 0.08 mm
Z = 2

Data collection top

Bruker SMART-1000 CCD area-detector diffractometer	3646 independent reflections
Radiation source: fine-focus sealed tube	2125 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
T_min = 0.941, T_max = 0.989	k = −6→6
5833 measured reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0454P)²] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max < 0.001
3646 reflections	Δρ_max = 0.15 e Å⁻³
229 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1493 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.19 (14)

Crystal data top

C₂₂H₃₅O₂P	V = 1102.4 (2) Å³
M_r = 362.47	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.4892 (13) Å	µ = 0.14 mm⁻¹
b = 5.8872 (6) Å	T = 298 K
c = 16.3531 (17) Å	0.45 × 0.11 × 0.08 mm
β = 94.696 (1)°

Data collection top

Bruker SMART-1000 CCD area-detector diffractometer	3646 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2125 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.989	R_int = 0.051
5833 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.119	Δρ_max = 0.15 e Å⁻³
S = 0.92	Δρ_min = −0.16 e Å⁻³
3646 reflections	Absolute structure: Flack (1983), 1493 Friedel pairs
229 parameters	Absolute structure parameter: 0.19 (14)
1 restraint

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.23767 (17)	0.3099 (5)	0.23127 (13)	0.0631 (7)
O2	0.0655 (2)	0.5689 (4)	0.26004 (16)	0.0743 (8)
P1	0.11424 (7)	0.33939 (18)	0.26861 (5)	0.0574 (3)
C1	0.3668 (4)	0.8147 (10)	0.1266 (3)	0.1001 (15)
H1	0.3503	0.9307	0.1671	0.120*
C2	0.2885 (3)	0.6094 (8)	0.1401 (2)	0.0784 (13)
H2A	0.2073	0.6561	0.1330	0.094*
H2B	0.3008	0.4947	0.0991	0.094*
C3	0.3131 (3)	0.5077 (7)	0.2245 (2)	0.0656 (11)
H3	0.2941	0.6204	0.2654	0.079*
C4	0.4397 (3)	0.4344 (8)	0.2429 (3)	0.0788 (13)
H4	0.4556	0.3199	0.2017	0.095*
C5	0.5175 (4)	0.6387 (9)	0.2281 (3)	0.1134 (18)
H5A	0.5059	0.7535	0.2692	0.136*
H5B	0.5986	0.5913	0.2351	0.136*
C6	0.4939 (4)	0.7439 (10)	0.1434 (3)	0.118 (2)
H6A	0.5436	0.8759	0.1392	0.141*
H6B	0.5136	0.6351	0.1022	0.141*
C7	0.3404 (5)	0.9182 (10)	0.0410 (3)	0.141 (2)
H7A	0.3626	0.8129	0.0003	0.211*
H7B	0.3837	1.0566	0.0371	0.211*
H7C	0.2583	0.9498	0.0322	0.211*
C8	0.4657 (3)	0.3225 (10)	0.3271 (3)	0.0899 (13)
H8	0.4093	0.1986	0.3305	0.108*
C9	0.5883 (4)	0.2143 (10)	0.3369 (4)	0.138 (2)
H9A	0.6015	0.1294	0.2884	0.207*
H9B	0.5936	0.1145	0.3835	0.207*
H9C	0.6462	0.3316	0.3450	0.207*
C10	0.4503 (4)	0.4809 (11)	0.4004 (3)	0.1130 (18)
H10A	0.5076	0.5998	0.4014	0.170*
H10B	0.4603	0.3955	0.4505	0.170*
H10C	0.3735	0.5462	0.3950	0.170*
C11	0.1394 (3)	0.2629 (7)	0.3751 (2)	0.0579 (11)
C12	0.1898 (3)	0.0589 (8)	0.4006 (3)	0.0777 (12)
H12	0.2096	−0.0463	0.3617	0.093*
C13	0.2111 (4)	0.0089 (9)	0.4834 (3)	0.0985 (16)
H13	0.2465	−0.1278	0.4995	0.118*
C14	0.1804 (5)	0.1593 (12)	0.5412 (3)	0.1094 (18)
H14	0.1933	0.1251	0.5967	0.131*
C15	0.1302 (4)	0.3623 (12)	0.5164 (3)	0.1083 (17)
H15	0.1102	0.4666	0.5556	0.130*
C16	0.1088 (3)	0.4143 (8)	0.4334 (2)	0.0821 (14)
H16	0.0738	0.5516	0.4176	0.099*
C17	0.0280 (3)	0.1208 (6)	0.2167 (2)	0.0535 (9)
H17	0.0700	−0.0232	0.2254	0.064*
C18	0.0112 (4)	0.1628 (9)	0.1254 (2)	0.0875 (14)
H18A	0.0867	0.1661	0.1029	0.105*
H18B	−0.0256	0.3095	0.1153	0.105*
C19	−0.0646 (4)	−0.0220 (11)	0.0820 (2)	0.1093 (17)
H19A	−0.0772	0.0142	0.0241	0.131*
H19B	−0.0238	−0.1662	0.0871	0.131*
C20	−0.1814 (4)	−0.0440 (10)	0.1178 (3)	0.1077 (17)
H20A	−0.2260	0.0944	0.1077	0.129*
H20B	−0.2251	−0.1684	0.0913	0.129*
C21	−0.1641 (3)	−0.0873 (8)	0.2087 (3)	0.0850 (15)
H21A	−0.1264	−0.2334	0.2183	0.102*
H21B	−0.2396	−0.0931	0.2312	0.102*
C22	−0.0900 (3)	0.0966 (8)	0.2526 (2)	0.0755 (13)
H22A	−0.1313	0.2402	0.2478	0.091*
H22B	−0.0776	0.0593	0.3104	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0564 (13)	0.0584 (18)	0.0767 (15)	−0.0131 (15)	0.0192 (11)	−0.0118 (15)
O2	0.0739 (17)	0.055 (2)	0.096 (2)	0.0069 (16)	0.0223 (14)	0.0092 (15)
P1	0.0537 (5)	0.0531 (6)	0.0667 (6)	−0.0016 (6)	0.0136 (4)	0.0013 (6)
C1	0.118 (4)	0.091 (4)	0.098 (3)	−0.049 (4)	0.050 (3)	−0.018 (3)
C2	0.081 (3)	0.080 (3)	0.078 (3)	−0.022 (3)	0.025 (2)	−0.011 (2)
C3	0.064 (3)	0.057 (3)	0.078 (3)	−0.024 (2)	0.021 (2)	−0.018 (2)
C4	0.053 (3)	0.083 (3)	0.102 (3)	−0.020 (2)	0.016 (2)	−0.037 (3)
C5	0.079 (3)	0.119 (5)	0.146 (5)	−0.050 (3)	0.031 (3)	−0.034 (4)
C6	0.106 (4)	0.126 (5)	0.130 (5)	−0.055 (3)	0.060 (3)	−0.032 (4)
C7	0.193 (6)	0.128 (6)	0.109 (4)	−0.060 (5)	0.062 (4)	0.013 (4)
C8	0.063 (2)	0.088 (3)	0.116 (4)	−0.007 (3)	−0.013 (2)	−0.017 (4)
C9	0.083 (3)	0.115 (5)	0.208 (6)	0.013 (3)	−0.039 (4)	−0.046 (4)
C10	0.110 (4)	0.134 (5)	0.093 (3)	0.004 (3)	−0.004 (3)	−0.026 (4)
C11	0.051 (2)	0.063 (3)	0.061 (2)	−0.0008 (19)	0.0085 (18)	−0.005 (2)
C12	0.088 (3)	0.076 (3)	0.068 (3)	0.005 (3)	−0.003 (2)	−0.007 (2)
C13	0.112 (4)	0.099 (4)	0.080 (3)	0.007 (3)	−0.024 (3)	0.011 (3)
C14	0.129 (4)	0.132 (6)	0.065 (3)	−0.011 (4)	−0.003 (3)	−0.001 (4)
C15	0.131 (4)	0.125 (6)	0.072 (3)	0.005 (4)	0.028 (3)	−0.023 (4)
C16	0.090 (3)	0.088 (4)	0.071 (3)	0.001 (3)	0.021 (2)	−0.014 (3)
C17	0.047 (2)	0.053 (2)	0.062 (2)	−0.0024 (18)	0.0107 (17)	0.0018 (19)
C18	0.085 (3)	0.116 (4)	0.061 (3)	−0.025 (3)	0.007 (2)	0.000 (3)
C19	0.104 (4)	0.156 (5)	0.067 (3)	−0.027 (3)	−0.001 (3)	−0.023 (3)
C20	0.074 (3)	0.140 (5)	0.104 (4)	−0.027 (3)	−0.019 (3)	−0.012 (3)
C21	0.053 (2)	0.096 (4)	0.106 (3)	−0.017 (2)	0.003 (2)	−0.003 (3)
C22	0.052 (2)	0.101 (4)	0.074 (3)	−0.011 (3)	0.0116 (19)	0.007 (3)

Geometric parameters (Å, º) top

O1—C3	1.461 (4)	C10—H10A	0.9600
O1—P1	1.599 (2)	C10—H10B	0.9600
O2—P1	1.465 (3)	C10—H10C	0.9600
P1—C17	1.794 (4)	C11—C16	1.372 (5)
P1—C11	1.799 (4)	C11—C12	1.382 (5)
C1—C6	1.523 (6)	C12—C13	1.388 (5)
C1—C2	1.533 (6)	C12—H12	0.9300
C1—C7	1.534 (6)	C13—C14	1.362 (7)
C1—H1	0.9800	C13—H13	0.9300
C2—C3	1.510 (5)	C14—C15	1.374 (7)
C2—H2A	0.9700	C14—H14	0.9300
C2—H2B	0.9700	C15—C16	1.393 (6)
C3—C4	1.523 (5)	C15—H15	0.9300
C3—H3	0.9800	C16—H16	0.9300
C4—C5	1.529 (6)	C17—C18	1.511 (4)
C4—C8	1.535 (6)	C17—C22	1.528 (4)
C4—H4	0.9800	C17—H17	0.9800
C5—C6	1.521 (6)	C18—C19	1.530 (6)
C5—H5A	0.9700	C18—H18A	0.9700
C5—H5B	0.9700	C18—H18B	0.9700
C6—H6A	0.9700	C19—C20	1.513 (5)
C6—H6B	0.9700	C19—H19A	0.9700
C7—H7A	0.9600	C19—H19B	0.9700
C7—H7B	0.9600	C20—C21	1.506 (5)
C7—H7C	0.9600	C20—H20A	0.9700
C8—C10	1.540 (6)	C20—H20B	0.9700
C8—C9	1.542 (6)	C21—C22	1.520 (5)
C8—H8	0.9800	C21—H21A	0.9700
C9—H9A	0.9600	C21—H21B	0.9700
C9—H9B	0.9600	C22—H22A	0.9700
C9—H9C	0.9600	C22—H22B	0.9700

C3—O1—P1	119.5 (2)	C8—C10—H10A	109.5
O2—P1—O1	114.04 (15)	C8—C10—H10B	109.5
O2—P1—C17	115.11 (17)	H10A—C10—H10B	109.5
O1—P1—C17	102.36 (14)	C8—C10—H10C	109.5
O2—P1—C11	110.69 (17)	H10A—C10—H10C	109.5
O1—P1—C11	105.39 (14)	H10B—C10—H10C	109.5
C17—P1—C11	108.49 (17)	C16—C11—C12	118.6 (4)
C6—C1—C2	108.9 (4)	C16—C11—P1	118.7 (3)
C6—C1—C7	112.8 (4)	C12—C11—P1	122.7 (3)
C2—C1—C7	111.7 (4)	C11—C12—C13	121.0 (4)
C6—C1—H1	107.7	C11—C12—H12	119.5
C2—C1—H1	107.7	C13—C12—H12	119.5
C7—C1—H1	107.7	C14—C13—C12	120.2 (5)
C3—C2—C1	112.1 (3)	C14—C13—H13	119.9
C3—C2—H2A	109.2	C12—C13—H13	119.9
C1—C2—H2A	109.2	C13—C14—C15	119.1 (5)
C3—C2—H2B	109.2	C13—C14—H14	120.4
C1—C2—H2B	109.2	C15—C14—H14	120.4
H2A—C2—H2B	107.9	C14—C15—C16	121.0 (5)
O1—C3—C2	108.5 (3)	C14—C15—H15	119.5
O1—C3—C4	108.8 (3)	C16—C15—H15	119.5
C2—C3—C4	113.4 (3)	C11—C16—C15	119.9 (4)
O1—C3—H3	108.7	C11—C16—H16	120.0
C2—C3—H3	108.7	C15—C16—H16	120.0
C4—C3—H3	108.7	C18—C17—C22	110.4 (3)
C3—C4—C5	107.9 (4)	C18—C17—P1	111.8 (3)
C3—C4—C8	114.3 (3)	C22—C17—P1	111.0 (2)
C5—C4—C8	114.0 (4)	C18—C17—H17	107.8
C3—C4—H4	106.7	C22—C17—H17	107.8
C5—C4—H4	106.7	P1—C17—H17	107.8
C8—C4—H4	106.7	C17—C18—C19	111.3 (4)
C6—C5—C4	113.7 (4)	C17—C18—H18A	109.4
C6—C5—H5A	108.8	C19—C18—H18A	109.4
C4—C5—H5A	108.8	C17—C18—H18B	109.4
C6—C5—H5B	108.8	C19—C18—H18B	109.4
C4—C5—H5B	108.8	H18A—C18—H18B	108.0
H5A—C5—H5B	107.7	C20—C19—C18	111.8 (4)
C1—C6—C5	111.9 (4)	C20—C19—H19A	109.3
C1—C6—H6A	109.2	C18—C19—H19A	109.3
C5—C6—H6A	109.2	C20—C19—H19B	109.3
C1—C6—H6B	109.2	C18—C19—H19B	109.3
C5—C6—H6B	109.2	H19A—C19—H19B	107.9
H6A—C6—H6B	107.9	C21—C20—C19	110.3 (3)
C1—C7—H7A	109.5	C21—C20—H20A	109.6
C1—C7—H7B	109.5	C19—C20—H20A	109.6
H7A—C7—H7B	109.5	C21—C20—H20B	109.6
C1—C7—H7C	109.5	C19—C20—H20B	109.6
H7A—C7—H7C	109.5	H20A—C20—H20B	108.1
H7B—C7—H7C	109.5	C20—C21—C22	111.7 (4)
C4—C8—C10	114.4 (4)	C20—C21—H21A	109.3
C4—C8—C9	112.3 (4)	C22—C21—H21A	109.3
C10—C8—C9	109.3 (4)	C20—C21—H21B	109.3
C4—C8—H8	106.8	C22—C21—H21B	109.3
C10—C8—H8	106.8	H21A—C21—H21B	108.0
C9—C8—H8	106.8	C17—C22—C21	111.5 (3)
C8—C9—H9A	109.5	C17—C22—H22A	109.3
C8—C9—H9B	109.5	C21—C22—H22A	109.3
H9A—C9—H9B	109.5	C17—C22—H22B	109.3
C8—C9—H9C	109.5	C21—C22—H22B	109.3
H9A—C9—H9C	109.5	H22A—C22—H22B	108.0
H9B—C9—H9C	109.5

C3—O1—P1—O2	25.3 (3)	O2—P1—C11—C12	−177.1 (3)
C3—O1—P1—C17	150.3 (3)	O1—P1—C11—C12	−53.3 (3)
C3—O1—P1—C11	−96.4 (3)	C17—P1—C11—C12	55.7 (3)
C6—C1—C2—C3	55.2 (5)	C16—C11—C12—C13	−1.2 (6)
C7—C1—C2—C3	−179.5 (4)	P1—C11—C12—C13	178.0 (3)
P1—O1—C3—C2	−93.0 (3)	C11—C12—C13—C14	1.3 (7)
P1—O1—C3—C4	143.1 (3)	C12—C13—C14—C15	−1.2 (8)
C1—C2—C3—O1	−178.3 (3)	C13—C14—C15—C16	1.0 (8)
C1—C2—C3—C4	−57.3 (5)	C12—C11—C16—C15	0.9 (6)
O1—C3—C4—C5	175.1 (3)	P1—C11—C16—C15	−178.2 (3)
C2—C3—C4—C5	54.3 (5)	C14—C15—C16—C11	−0.9 (7)
O1—C3—C4—C8	−57.0 (4)	O2—P1—C17—C18	60.0 (3)
C2—C3—C4—C8	−177.9 (4)	O1—P1—C17—C18	−64.3 (3)
C3—C4—C5—C6	−53.9 (5)	C11—P1—C17—C18	−175.4 (3)
C8—C4—C5—C6	178.1 (4)	O2—P1—C17—C22	−63.8 (3)
C2—C1—C6—C5	−54.5 (5)	O1—P1—C17—C22	171.9 (3)
C7—C1—C6—C5	−179.2 (4)	C11—P1—C17—C22	60.8 (3)
C4—C5—C6—C1	56.4 (6)	C22—C17—C18—C19	−54.7 (5)
C3—C4—C8—C10	−64.6 (5)	P1—C17—C18—C19	−178.8 (3)
C5—C4—C8—C10	60.1 (5)	C17—C18—C19—C20	55.9 (5)
C3—C4—C8—C9	170.0 (4)	C18—C19—C20—C21	−55.8 (6)
C5—C4—C8—C9	−65.3 (5)	C19—C20—C21—C22	56.0 (5)
O2—P1—C11—C16	2.0 (3)	C18—C17—C22—C21	55.1 (4)
O1—P1—C11—C16	125.8 (3)	P1—C17—C22—C21	179.7 (3)
C17—P1—C11—C16	−125.2 (3)	C20—C21—C22—C17	−56.2 (5)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₃₅O₂P
M_r	362.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	11.4892 (13), 5.8872 (6), 16.3531 (17)
β (°)	94.696 (1)
V (Å³)	1102.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.45 × 0.11 × 0.08

Data collection
Diffractometer	Bruker SMART1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.941, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	5833, 3646, 2125
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.119, 0.92
No. of reflections	3646
No. of parameters	229
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16
Absolute structure	Flack (1983), 1493 Friedel pairs
Absolute structure parameter	0.19 (14)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x, y−1, z.

Acknowledgements

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

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fu, B. & Zhao, C.-Q. (2010). Acta Cryst. E66, o859. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar