(RP)-Menthyl (1-hydroxy­cyclo­hexyl)phenyl­phosphinate

Fu, B.; Zhao, C.-Q.

doi:10.1107/S1600536810009219

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o859

doi:10.1107/S1600536810009219

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(R_P)-Menthyl (1-hydroxycyclohexyl)phenylphosphinate

Baoci Fu ^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 24 December 2009; accepted 11 March 2010; online 17 March 2010)

The title compound, C₂₂H₃₅O₃P, features a tetrahedral P atom bonded to a phenyl ring, a hydroxycyclohexyl unit and the O atom of a menthyl group. The axial chirality at phosphorus is R_P. In the crystal, molecules are connected through O—H⋯O hydrogen bonds involving the hydroxy and P=O groups, forming chains along the 2₁ screw axis. The methyl groups of the isopropyl fragment in the menthyl unit are disordered over two sites of equal occupancy.

Related literature

For general background to α-hydroxy alkylphosphonates, see: Kim & Wiemer (2003 ). For the structures of related phenylphosphinates, see: Sheldrick et al. (1981 ); Chaloner et al. (1991 ); Grice et al. (2004 ).

Experimental

Crystal data

C₂₂H₃₅O₃P
M_r = 378.47
Monoclinic, P 2₁
a = 10.1808 (11) Å
b = 11.0611 (13) Å
c = 10.4207 (12) Å
β = 106.201 (1)°
V = 1126.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 298 K
0.42 × 0.32 × 0.26 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.944, T_max = 0.965
5667 measured reflections
3787 independent reflections
3248 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.096
S = 1.06
3787 reflections
263 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 1685 Friedel pairs
Flack parameter: 0.14 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.76 (3)	1.94 (3)	2.695 (3)	170 (3)
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009219/bh2267sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009219/bh2267Isup2.hkl

checkCIF report

Comment top

α-Hydroxy alkylphosphonates have received attention both as substrates for the preparation of other α-substituted phosphonates, and because of their potential biological activity. For example, representatives of this class act as inhibitors of farnesyl protein transferase (FPTase), renin, and HIV protease (Kim & Wiemer, 2003).

The P-chiral title compound, which can be synthesized by addition of (R_P)-menthyl-phenylphosphinate to cyclohexanone (see Experimental), is comprised of fully extended substituents: phenyl, menthyl and α-hydroxycyclohexyl. The configuration of the central P atom is R and the four groups around the P atom form an irregular tetrahedron as found in tert-butyl diphenylphosphinate (Grice et al., 2004). The bond angles are C1—P—C17 = 107.13 (11)°, O1—P—C1 = 107.06 (10)°, O1—P—C17 = 102.87 (9)°, O2—P—O1 = 113.87 (9)°, O2—P—C17 = 113.18 (11)° and O2—P—C1 = 112.05 (11)°, which compare with angles observed in related phenylphosphinate derivatives bearing a menthyl group (Chaloner et al., 1991; Sheldrick et al., 1981). Part of methyl groups (C14 and C15) were found to be disordered over two sites with equal occupancies.

Intramolecular O3—H3···O2 hydrogen bonds are found in the crystal structure. The crystal packing is further stabilized by van der Waals interactions.

Related literature top

For general background to α-hydroxy alkylphosphonates, see: Kim & Wiemer (2003). For the structures of related phenylphosphinates, see: Sheldrick et al. (1981); Chaloner et al. (1991); Grice et al. (2004).

Experimental top

Cyclohexanone was added to a stirred DMF solution of (R_P)-menthyl-phenylphosphinate in a flask and the mixture was stirred for 48 h at room temperature. After washing with water, the resulting solid was dried, and recrystallized from diethyl ether, to afford the pure title product.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 the title compound. H atoms have been omitted for clarity. Primed atoms C14' and C15' are disordered with C14 and C15, respectively.

(R_P)-Menthyl (1-hydroxycyclohexyl)phenylphosphinate top

Crystal data top

C₂₂H₃₅O₃P	F(000) = 412
M_r = 378.47	D_x = 1.115 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2598 reflections
a = 10.1808 (11) Å	θ = 2.5–24.8°
b = 11.0611 (13) Å	µ = 0.14 mm⁻¹
c = 10.4207 (12) Å	T = 298 K
β = 106.201 (1)°	Block, colorless
V = 1126.9 (2) Å³	0.42 × 0.32 × 0.26 mm
Z = 2

Data collection top

Siemens SMART CCD area-detector diffractometer	3787 independent reflections
Radiation source: fine-focus sealed tube	3248 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→12
T_min = 0.944, T_max = 0.965	k = −13→13
5667 measured reflections	l = −12→10

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0437P)² + 0.1698P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3787 reflections	Δρ_max = 0.16 e Å⁻³
263 parameters	Δρ_min = −0.24 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1685 Friedel pairs
0 constraints	Absolute structure parameter: 0.14 (10)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₂H₃₅O₃P	V = 1126.9 (2) Å³
M_r = 378.47	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.1808 (11) Å	µ = 0.14 mm⁻¹
b = 11.0611 (13) Å	T = 298 K
c = 10.4207 (12) Å	0.42 × 0.32 × 0.26 mm
β = 106.201 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	3787 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3248 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.965	R_int = 0.019
5667 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	Δρ_max = 0.16 e Å⁻³
S = 1.06	Δρ_min = −0.24 e Å⁻³
3787 reflections	Absolute structure: Flack (1983), 1685 Friedel pairs
263 parameters	Absolute structure parameter: 0.14 (10)
1 restraint

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.95710 (16)	0.72151 (14)	0.74639 (14)	0.0404 (4)
O2	0.97738 (18)	0.87366 (15)	0.56708 (17)	0.0462 (4)
O3	0.8831 (2)	0.52789 (16)	0.54628 (18)	0.0454 (5)
H3	0.930 (3)	0.488 (3)	0.520 (3)	0.056 (10)*
P1	0.99001 (6)	0.74570 (6)	0.60864 (6)	0.03512 (16)
C1	1.1586 (3)	0.6871 (2)	0.6245 (2)	0.0410 (6)
C2	1.2450 (3)	0.7469 (3)	0.5653 (3)	0.0561 (7)
H2	1.2159	0.8181	0.5184	0.067*
C3	1.3736 (4)	0.7031 (3)	0.5743 (4)	0.0805 (11)
H3A	1.4317	0.7456	0.5359	0.097*
C4	1.4161 (3)	0.5965 (4)	0.6402 (4)	0.0815 (11)
H4	1.5020	0.5657	0.6438	0.098*
C5	1.3327 (3)	0.5355 (3)	0.7005 (4)	0.0720 (9)
H5	1.3626	0.4641	0.7465	0.086*
C6	1.2035 (3)	0.5802 (3)	0.6929 (3)	0.0551 (7)
H6	1.1466	0.5386	0.7336	0.066*
C7	0.8846 (3)	0.8021 (3)	0.9295 (3)	0.0561 (7)
H7	0.8856	0.7192	0.9628	0.067*
C8	0.9937 (3)	0.8099 (3)	0.8559 (2)	0.0452 (6)
H8	0.9926	0.8912	0.8181	0.054*
C9	1.1352 (3)	0.7835 (3)	0.9449 (3)	0.0571 (8)
H9A	1.2009	0.7927	0.8937	0.068*
H9B	1.1391	0.7004	0.9752	0.068*
C10	1.1745 (3)	0.8673 (3)	1.0659 (3)	0.0697 (9)
H10	1.1755	0.9504	1.0336	0.084*
C11	1.0682 (4)	0.8595 (4)	1.1413 (3)	0.0788 (10)
H11A	1.0902	0.9170	1.2145	0.095*
H11B	1.0699	0.7791	1.1791	0.095*
C12	0.9261 (4)	0.8856 (4)	1.0522 (3)	0.0797 (11)
H12A	0.9222	0.9689	1.0222	0.096*
H12B	0.8608	0.8763	1.1037	0.096*
C13	0.7400 (3)	0.8263 (4)	0.8383 (3)	0.0776 (11)
H13	0.7166	0.7564	0.7786	0.093*
C14	0.627 (3)	0.8350 (16)	0.911 (3)	0.095 (5)	0.50
H14A	0.6335	0.9114	0.9559	0.143*	0.50
H14B	0.6381	0.7707	0.9749	0.143*	0.50
H14C	0.5388	0.8282	0.8467	0.143*	0.50
C15	0.714 (4)	0.938 (4)	0.748 (3)	0.108 (6)	0.50
H15A	0.7745	0.9366	0.6920	0.162*	0.50
H15B	0.7302	1.0094	0.8022	0.162*	0.50
H15C	0.6209	0.9371	0.6934	0.162*	0.50
C14'	0.635 (3)	0.7783 (17)	0.912 (3)	0.095 (5)	0.50
H14D	0.6474	0.8216	0.9944	0.143*	0.50
H14E	0.6507	0.6936	0.9306	0.143*	0.50
H14F	0.5438	0.7903	0.8562	0.143*	0.50
C15'	0.735 (4)	0.959 (4)	0.789 (3)	0.108 (6)	0.50
H15D	0.7474	1.0123	0.8642	0.162*	0.50
H15E	0.6473	0.9740	0.7266	0.162*	0.50
H15R	0.8057	0.9717	0.7467	0.162*	0.50
C16	1.3180 (4)	0.8374 (5)	1.1542 (4)	0.1122 (16)
H16A	1.3206	0.7549	1.1833	0.168*
H16B	1.3403	0.8899	1.2306	0.168*
H16C	1.3831	0.8487	1.1040	0.168*
C17	0.8687 (2)	0.6464 (2)	0.4925 (2)	0.0352 (5)
C18	0.8980 (3)	0.6531 (2)	0.3562 (2)	0.0448 (6)
H18A	0.8993	0.7372	0.3301	0.054*
H18B	0.9877	0.6192	0.3638	0.054*
C19	0.7919 (3)	0.5853 (3)	0.2483 (3)	0.0588 (8)
H19A	0.8104	0.5973	0.1628	0.071*
H19B	0.7987	0.4995	0.2681	0.071*
C20	0.6479 (3)	0.6285 (3)	0.2392 (3)	0.0709 (9)
H20A	0.6380	0.7123	0.2105	0.085*
H20B	0.5823	0.5807	0.1733	0.085*
C21	0.6187 (3)	0.6171 (3)	0.3728 (3)	0.0657 (9)
H21A	0.6223	0.5326	0.3983	0.079*
H21B	0.5272	0.6467	0.3654	0.079*
C22	0.7219 (3)	0.6887 (3)	0.4808 (3)	0.0492 (7)
H22A	0.7022	0.6777	0.5660	0.059*
H22B	0.7136	0.7741	0.4590	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0456 (9)	0.0393 (11)	0.0388 (8)	−0.0032 (8)	0.0161 (7)	−0.0047 (7)
O2	0.0508 (11)	0.0335 (10)	0.0567 (10)	−0.0007 (8)	0.0190 (8)	0.0038 (8)
O3	0.0580 (12)	0.0339 (10)	0.0494 (11)	−0.0026 (9)	0.0233 (9)	−0.0016 (8)
P1	0.0363 (3)	0.0318 (3)	0.0396 (3)	−0.0007 (3)	0.0144 (2)	0.0000 (3)
C1	0.0396 (14)	0.0410 (14)	0.0434 (14)	0.0005 (11)	0.0132 (11)	−0.0020 (12)
C2	0.0513 (15)	0.0501 (15)	0.0746 (17)	0.0069 (17)	0.0305 (13)	0.0119 (19)
C3	0.058 (2)	0.078 (3)	0.119 (3)	0.0097 (17)	0.048 (2)	0.018 (2)
C4	0.0510 (19)	0.082 (3)	0.119 (3)	0.0225 (19)	0.035 (2)	0.012 (2)
C5	0.059 (2)	0.063 (2)	0.093 (2)	0.0203 (17)	0.0181 (18)	0.0197 (18)
C6	0.0487 (17)	0.0538 (18)	0.0643 (18)	0.0038 (14)	0.0184 (14)	0.0140 (15)
C7	0.0615 (18)	0.0665 (18)	0.0429 (15)	0.0104 (15)	0.0191 (14)	−0.0072 (13)
C8	0.0591 (17)	0.0389 (14)	0.0371 (14)	−0.0023 (14)	0.0128 (13)	−0.0048 (12)
C9	0.0543 (17)	0.065 (2)	0.0514 (16)	−0.0048 (13)	0.0134 (13)	−0.0063 (13)
C10	0.082 (2)	0.069 (2)	0.0504 (17)	−0.0200 (18)	0.0051 (16)	−0.0067 (16)
C11	0.094 (3)	0.092 (3)	0.0444 (17)	−0.004 (2)	0.0104 (18)	−0.0162 (18)
C12	0.095 (3)	0.096 (3)	0.0519 (18)	0.014 (2)	0.0266 (18)	−0.0245 (19)
C13	0.062 (2)	0.114 (3)	0.0585 (19)	0.029 (2)	0.0188 (17)	−0.015 (2)
C14	0.067 (7)	0.137 (16)	0.090 (7)	0.030 (11)	0.034 (5)	−0.024 (13)
C15	0.099 (12)	0.131 (17)	0.072 (14)	0.055 (11)	−0.012 (11)	−0.015 (12)
C14'	0.067 (6)	0.137 (16)	0.089 (7)	0.030 (12)	0.034 (5)	−0.024 (13)
C15'	0.099 (12)	0.130 (17)	0.072 (14)	0.055 (11)	−0.012 (11)	−0.014 (12)
C16	0.089 (3)	0.148 (4)	0.078 (3)	−0.027 (3)	−0.011 (2)	−0.026 (3)
C17	0.0406 (14)	0.0327 (13)	0.0352 (12)	−0.0009 (10)	0.0155 (11)	−0.0018 (10)
C18	0.0491 (15)	0.0478 (16)	0.0400 (13)	0.0045 (12)	0.0163 (12)	0.0001 (12)
C19	0.069 (2)	0.0644 (19)	0.0406 (15)	0.0064 (16)	0.0124 (14)	−0.0084 (14)
C20	0.061 (2)	0.085 (2)	0.0560 (18)	0.0042 (17)	−0.0025 (15)	−0.0180 (16)
C21	0.0420 (16)	0.081 (2)	0.070 (2)	−0.0046 (15)	0.0094 (15)	−0.0206 (17)
C22	0.0413 (15)	0.0544 (17)	0.0514 (15)	0.0028 (13)	0.0121 (12)	−0.0086 (13)

Geometric parameters (Å, º) top

O1—C8	1.469 (3)	C13—C15'	1.55 (5)
O1—P1	1.5853 (16)	C13—C14	1.55 (3)
O2—P1	1.4752 (18)	C13—C14'	1.57 (3)
O3—C17	1.417 (3)	C13—H13	0.9800
O3—H3	0.76 (3)	C14—H14A	0.9600
P1—C1	1.799 (3)	C14—H14B	0.9600
P1—C17	1.834 (2)	C14—H14C	0.9600
C1—C2	1.376 (4)	C15—H15A	0.9600
C1—C6	1.390 (4)	C15—H15B	0.9600
C2—C3	1.375 (4)	C15—H15C	0.9600
C2—H2	0.9300	C14'—H14D	0.9600
C3—C4	1.371 (5)	C14'—H14E	0.9600
C3—H3A	0.9300	C14'—H14F	0.9600
C4—C5	1.367 (5)	C15'—H15D	0.9600
C4—H4	0.9300	C15'—H15E	0.9600
C5—C6	1.387 (4)	C15'—H15R	0.9600
C5—H5	0.9300	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—C8	1.518 (4)	C16—H16C	0.9600
C7—C13	1.537 (4)	C17—C18	1.533 (3)
C7—C12	1.537 (4)	C17—C22	1.538 (3)
C7—H7	0.9800	C18—C19	1.522 (4)
C8—C9	1.508 (4)	C18—H18A	0.9700
C8—H8	0.9800	C18—H18B	0.9700
C9—C10	1.526 (4)	C19—C20	1.520 (4)
C9—H9A	0.9700	C19—H19A	0.9700
C9—H9B	0.9700	C19—H19B	0.9700
C10—C11	1.507 (5)	C20—C21	1.507 (4)
C10—C16	1.529 (5)	C20—H20A	0.9700
C10—H10	0.9800	C20—H20B	0.9700
C11—C12	1.513 (5)	C21—C22	1.529 (4)
C11—H11A	0.9700	C21—H21A	0.9700
C11—H11B	0.9700	C21—H21B	0.9700
C12—H12A	0.9700	C22—H22A	0.9700
C12—H12B	0.9700	C22—H22B	0.9700
C13—C15	1.53 (5)

C8—O1—P1	121.25 (15)	C7—C13—C14'	107.6 (10)
C17—O3—H3	114 (2)	C15'—C13—C14'	121.0 (17)
O2—P1—O1	113.87 (9)	C15—C13—H13	106.1
O2—P1—C1	112.05 (11)	C7—C13—H13	106.1
O1—P1—C1	107.06 (10)	C14—C13—H13	106.1
O2—P1—C17	113.18 (11)	C13—C14—H14A	109.5
O1—P1—C17	102.87 (9)	C13—C14—H14B	109.5
C1—P1—C17	107.13 (11)	C13—C14—H14C	109.5
C2—C1—C6	118.6 (2)	C13—C15—H15A	109.5
C2—C1—P1	119.9 (2)	C13—C15—H15B	109.5
C6—C1—P1	121.5 (2)	C13—C15—H15C	109.5
C3—C2—C1	121.0 (3)	C13—C14'—H14D	109.5
C3—C2—H2	119.5	C13—C14'—H14E	109.5
C1—C2—H2	119.5	H14D—C14'—H14E	109.5
C4—C3—C2	119.9 (3)	C13—C14'—H14F	109.5
C4—C3—H3A	120.0	H14D—C14'—H14F	109.5
C2—C3—H3A	120.0	H14E—C14'—H14F	109.5
C5—C4—C3	120.3 (3)	C13—C15'—H15D	109.5
C5—C4—H4	119.8	C13—C15'—H15E	109.5
C3—C4—H4	119.8	H15D—C15'—H15E	109.5
C4—C5—C6	119.8 (3)	C13—C15'—H15R	109.5
C4—C5—H5	120.1	H15D—C15'—H15R	109.5
C6—C5—H5	120.1	H15E—C15'—H15R	109.5
C5—C6—C1	120.2 (3)	C10—C16—H16A	109.5
C5—C6—H6	119.9	C10—C16—H16B	109.5
C1—C6—H6	119.9	H16A—C16—H16B	109.5
C8—C7—C13	112.8 (2)	C10—C16—H16C	109.5
C8—C7—C12	108.4 (3)	H16A—C16—H16C	109.5
C13—C7—C12	113.8 (3)	H16B—C16—H16C	109.5
C8—C7—H7	107.2	O3—C17—C18	112.73 (19)
C13—C7—H7	107.2	O3—C17—C22	107.7 (2)
C12—C7—H7	107.2	C18—C17—C22	110.4 (2)
O1—C8—C9	109.9 (2)	O3—C17—P1	108.49 (16)
O1—C8—C7	107.0 (2)	C18—C17—P1	108.25 (17)
C9—C8—C7	112.7 (2)	C22—C17—P1	109.30 (16)
O1—C8—H8	109.1	C19—C18—C17	112.3 (2)
C9—C8—H8	109.1	C19—C18—H18A	109.1
C7—C8—H8	109.1	C17—C18—H18A	109.1
C8—C9—C10	112.1 (2)	C19—C18—H18B	109.1
C8—C9—H9A	109.2	C17—C18—H18B	109.1
C10—C9—H9A	109.2	H18A—C18—H18B	107.9
C8—C9—H9B	109.2	C20—C19—C18	111.4 (2)
C10—C9—H9B	109.2	C20—C19—H19A	109.3
H9A—C9—H9B	107.9	C18—C19—H19A	109.3
C11—C10—C9	109.6 (3)	C20—C19—H19B	109.3
C11—C10—C16	112.2 (3)	C18—C19—H19B	109.3
C9—C10—C16	110.6 (3)	H19A—C19—H19B	108.0
C11—C10—H10	108.1	C21—C20—C19	110.6 (3)
C9—C10—H10	108.1	C21—C20—H20A	109.5
C16—C10—H10	108.1	C19—C20—H20A	109.5
C10—C11—C12	111.8 (3)	C21—C20—H20B	109.5
C10—C11—H11A	109.3	C19—C20—H20B	109.5
C12—C11—H11A	109.3	H20A—C20—H20B	108.1
C10—C11—H11B	109.3	C20—C21—C22	111.4 (3)
C12—C11—H11B	109.3	C20—C21—H21A	109.3
H11A—C11—H11B	107.9	C22—C21—H21A	109.3
C11—C12—C7	113.0 (3)	C20—C21—H21B	109.3
C11—C12—H12A	109.0	C22—C21—H21B	109.3
C7—C12—H12A	109.0	H21A—C21—H21B	108.0
C11—C12—H12B	109.0	C21—C22—C17	110.7 (2)
C7—C12—H12B	109.0	C21—C22—H22A	109.5
H12A—C12—H12B	107.8	C17—C22—H22A	109.5
C15—C13—C7	119.6 (14)	C21—C22—H22B	109.5
C7—C13—C15'	108.0 (13)	C17—C22—H22B	109.5
C15—C13—C14	103.0 (17)	H22A—C22—H22B	108.1
C7—C13—C14	115.1 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.76 (3)	1.94 (3)	2.695 (3)	170 (3)

Symmetry code: (i) −x+2, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₃₅O₃P
M_r	378.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	10.1808 (11), 11.0611 (13), 10.4207 (12)
β (°)	106.201 (1)
V (Å³)	1126.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.42 × 0.32 × 0.26

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.944, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	5667, 3787, 3248
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.096, 1.06
No. of reflections	3787
No. of parameters	263
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.24
Absolute structure	Flack (1983), 1685 Friedel pairs
Absolute structure parameter	0.14 (10)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
O3—H3···O2ⁱ	0.76 (3)	1.94 (3)	2.695 (3)	170 (3)

Symmetry code: (i) −x+2, y−1/2, −z+1.

Acknowledgements

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

References

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