2-Isopropyl-5-methyl­cyclo­hexyl diphenyl­phospho­namidate

Meng, F.-J.; Zhao, C.-Q.

doi:10.1107/S1600536811010580

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o998

doi:10.1107/S1600536811010580

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2-Isopropyl-5-methylcyclohexyl diphenylphosphonamidate

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 compound, C₂₂H₃₀NO₂P, the P atom has an irregular tetrahedral geometry. In the crystal, molecules are connected by N—H⋯O hydrogen-bonding interactions, giving rise to a chain along the b axis. The phenyl ring of the anilino group is twisted by 77.40 (16)° relative to the other phenyl ring. The absolute configuration of phosphorus is S_p.

Related literature

For applications of chiral phosphinoylimines, see: Benamer et al. (2010 ). For related structures, see: Balakrishna et al. (2001 ). For the use of chiral organophosphorus compounds in metal-catalyzed and organocatalytic reactions, see: Steinberg (1950 ).

Experimental

Crystal data

C₂₂H₃₀NO₂P
M_r = 371.44
Monoclinic, P 2₁
a = 8.6934 (8) Å
b = 5.4716 (5) Å
c = 22.100 (2) Å
β = 101.006 (1)°
V = 1031.90 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 298 K
0.45 × 0.36 × 0.17 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.936, T_max = 0.975
5183 measured reflections
3589 independent reflections
2814 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.104
S = 1.09
3589 reflections
238 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1550 Friedel pairs
Flack parameter: −0.06 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H6⋯O2ⁱ	0.86	2.24	3.053 (3)	157
Symmetry code: (i) x, y-1, z.

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/S1600536811010580/bq2285sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010580/bq2285Isup2.hkl

checkCIF report

Comment top

The catalytic asymmetric synthesis of chiral organophosphorus compounds has attracted considerable attention in the past decades, for these compounds can serve as precursors of many biologically active molecules and play an important role in metal-catalyzed and organocatalytic reactions (Steinberg, 1950). The molecular structure of the P-chiral title compound, (I), is composed of 2-isopropyl-5-methylcyclohexyl phenylphosphinate core with phenylamine (Fig. 1.). The configuration of the central P atom is S. The four groups around the P atom form a irregular tetrahedron (Benamer et al., 2010). The torsion angles of the O(2)–P(1)–N(1)–C(3) and O(1)–P(1)–N(1)–C(3) are -45.0 (3) Å and -170.0 (2) Å. In the crystal structure (Balakrishna et al., 2001), intermolecular N—H···O hydrogen bonds connect molecules into a one-dimensional chain (Table 1. , Fig. 2.).

Related literature top

For applications of chiral phosphinoylimines, see: Benamer et al. (2010). For related structures, see: Balakrishna et al. (2001). For the use of chiral organophosphorus compounds in metal-catalyzed and organocatalytic reactions, see: Steinberg (1950)

Experimental top

Carbon tetrachloride was added to a solution of 2-isopropyl-5-methylcyclohexyl phenylphosphinate dissolved in dry ether and phenylamine. The reaction mixture was stirred for 38 h at room temperature. After washing with water, the resulting solution was purified by preparative TLC on silica gel to afford optically pure product. Single crystals of the title compound suitable for x–ray diffraction were obtained by slow evaporation of ether solution.

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 (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The one–dimensional chain of (I), linked by N—H···O hydrogen bonds.

N-({[5-methyl-2-(propan-2-yl)cyclohexyl]oxy}(phenyl)phosphoryl)aniline top

Crystal data top

C₂₂H₃₀NO₂P	F(000) = 400
M_r = 371.44	D_x = 1.195 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1942 reflections
a = 8.6934 (8) Å	θ = 2.7–25.2°
b = 5.4716 (5) Å	µ = 0.15 mm⁻¹
c = 22.100 (2) Å	T = 298 K
β = 101.006 (1)°	Block, colorless
V = 1031.90 (17) Å³	0.45 × 0.36 × 0.17 mm
Z = 2

Data collection top

Siemens SMART CCD area-detector diffractometer	3589 independent reflections
Radiation source: fine-focus sealed tube	2814 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.936, T_max = 0.975	k = −6→6
5183 measured reflections	l = −26→13

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0475P)² + 0.0269P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
3589 reflections	Δρ_max = 0.15 e Å⁻³
238 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1550 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (12)

Crystal data top

C₂₂H₃₀NO₂P	V = 1031.90 (17) Å³
M_r = 371.44	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.6934 (8) Å	µ = 0.15 mm⁻¹
b = 5.4716 (5) Å	T = 298 K
c = 22.100 (2) Å	0.45 × 0.36 × 0.17 mm
β = 101.006 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	3589 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2814 reflections with I > 2σ(I)
T_min = 0.936, T_max = 0.975	R_int = 0.021
5183 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.104	Δρ_max = 0.15 e Å⁻³
S = 1.09	Δρ_min = −0.25 e Å⁻³
3589 reflections	Absolute structure: Flack (1983), 1550 Friedel pairs
238 parameters	Absolute structure parameter: −0.06 (12)
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
C1	−0.0896 (4)	0.6404 (9)	0.08739 (15)	0.0830 (12)
H1A	−0.0743	0.4702	0.0778	0.100*
H1B	−0.1840	0.6970	0.0602	0.100*
P1	0.36057 (8)	0.79230 (14)	0.29338 (3)	0.03738 (19)
C2	0.5704 (3)	0.8039 (6)	0.30983 (11)	0.0402 (6)
O2	0.2888 (2)	1.0296 (3)	0.30075 (8)	0.0446 (5)
C3	0.2897 (3)	0.5828 (5)	0.39742 (11)	0.0351 (6)
O1	0.3227 (2)	0.6846 (4)	0.22586 (8)	0.0436 (5)
C4	0.3333 (4)	0.7801 (7)	0.49563 (12)	0.0570 (8)
H4	0.3754	0.9087	0.5210	0.068*
C5	0.3513 (3)	0.7748 (7)	0.43486 (11)	0.0459 (7)
H5	0.4046	0.9000	0.4193	0.055*
N1	0.3040 (3)	0.5712 (4)	0.33461 (10)	0.0424 (6)
H6	0.2807	0.4340	0.3161	0.051*
C7	0.0423 (3)	0.6000 (7)	0.19730 (13)	0.0543 (8)
H7A	0.0304	0.6289	0.2395	0.065*
H7B	0.0660	0.4282	0.1934	0.065*
C8	0.6462 (4)	0.9995 (6)	0.28841 (14)	0.0566 (9)
H8	0.5884	1.1207	0.2648	0.068*
C9	0.2115 (3)	0.3967 (6)	0.42092 (13)	0.0458 (8)
H9	0.1710	0.2659	0.3960	0.055*
C10	0.1771 (3)	0.7509 (6)	0.18402 (11)	0.0439 (8)
H10	0.1549	0.9240	0.1899	0.053*
C11	0.2538 (4)	0.5968 (7)	0.51885 (14)	0.0611 (9)
H11	0.2408	0.6024	0.5596	0.073*
C12	0.6582 (4)	0.6285 (6)	0.34548 (13)	0.0507 (8)
H12	0.6085	0.4972	0.3604	0.061*
C13	0.2020 (4)	0.7132 (6)	0.11828 (12)	0.0534 (9)
H13	0.2114	0.5362	0.1132	0.064*
C14	0.1938 (4)	0.4062 (7)	0.48197 (14)	0.0590 (9)
H14	0.1406	0.2815	0.4979	0.071*
C15	0.8088 (4)	1.0140 (7)	0.30229 (16)	0.0660 (10)
H15	0.8597	1.1438	0.2873	0.079*
C16	−0.1120 (4)	0.6599 (7)	0.15376 (15)	0.0641 (10)
H16	−0.1400	0.8292	0.1613	0.077*
C17	0.3526 (5)	0.8226 (9)	0.10465 (16)	0.0738 (11)
H17	0.4384	0.7565	0.1356	0.089*
C18	0.0482 (4)	0.7874 (9)	0.07536 (13)	0.0765 (10)
H18A	0.0285	0.9595	0.0812	0.092*
H18B	0.0590	0.7642	0.0329	0.092*
C19	0.8948 (4)	0.8369 (7)	0.33812 (16)	0.0634 (11)
H19	1.0035	0.8479	0.3477	0.076*
C20	0.3841 (5)	0.7449 (10)	0.04193 (16)	0.1023 (16)
H20A	0.3830	0.5697	0.0392	0.153*
H20B	0.4847	0.8050	0.0370	0.153*
H20C	0.3044	0.8109	0.0100	0.153*
C21	0.3603 (7)	1.0937 (9)	0.1111 (3)	0.1244 (19)
H21A	0.2736	1.1659	0.0835	0.187*
H21B	0.4567	1.1518	0.1013	0.187*
H21C	0.3555	1.1379	0.1527	0.187*
C22	−0.2440 (5)	0.4933 (9)	0.1665 (2)	0.0947 (14)
H22A	−0.2187	0.3263	0.1595	0.142*
H22B	−0.3403	0.5366	0.1396	0.142*
H22C	−0.2556	0.5128	0.2086	0.142*
C23	0.8201 (4)	0.6464 (7)	0.35934 (15)	0.0633 (10)
H23	0.8783	0.5267	0.3834	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.074 (3)	0.110 (3)	0.054 (2)	0.010 (3)	−0.0144 (19)	−0.006 (2)
P1	0.0433 (4)	0.0378 (4)	0.0310 (3)	0.0023 (4)	0.0073 (3)	−0.0027 (4)
C2	0.0466 (16)	0.0431 (15)	0.0316 (13)	−0.0011 (18)	0.0092 (11)	−0.0062 (16)
O2	0.0501 (13)	0.0402 (11)	0.0438 (11)	0.0053 (10)	0.0098 (9)	−0.0045 (10)
C3	0.0356 (15)	0.0374 (15)	0.0322 (14)	0.0056 (13)	0.0061 (11)	−0.0004 (13)
O1	0.0471 (11)	0.0513 (11)	0.0321 (10)	0.0098 (10)	0.0065 (8)	−0.0039 (8)
C4	0.083 (2)	0.0498 (17)	0.0370 (15)	0.002 (2)	0.0088 (14)	−0.0086 (18)
C5	0.0541 (17)	0.0452 (16)	0.0381 (15)	−0.0033 (18)	0.0077 (12)	−0.0003 (17)
N1	0.0543 (16)	0.0373 (13)	0.0365 (13)	−0.0036 (12)	0.0110 (11)	−0.0059 (11)
C7	0.052 (2)	0.069 (2)	0.0417 (17)	0.0033 (18)	0.0096 (14)	−0.0063 (17)
C8	0.057 (2)	0.056 (2)	0.056 (2)	−0.0012 (18)	0.0110 (16)	0.0024 (17)
C9	0.052 (2)	0.0386 (16)	0.0476 (18)	−0.0023 (14)	0.0106 (15)	0.0001 (14)
C10	0.0489 (17)	0.048 (2)	0.0322 (13)	0.0108 (16)	0.0015 (12)	−0.0048 (14)
C11	0.087 (3)	0.064 (2)	0.0363 (17)	0.011 (2)	0.0221 (17)	0.0024 (18)
C12	0.049 (2)	0.054 (2)	0.0504 (18)	0.0049 (16)	0.0124 (15)	0.0018 (16)
C13	0.070 (2)	0.058 (2)	0.0328 (15)	0.0075 (17)	0.0113 (15)	0.0003 (14)
C14	0.074 (3)	0.058 (2)	0.051 (2)	0.0003 (18)	0.0259 (18)	0.0130 (18)
C15	0.055 (2)	0.069 (2)	0.077 (2)	−0.021 (2)	0.0205 (19)	−0.011 (2)
C16	0.055 (2)	0.076 (2)	0.057 (2)	0.005 (2)	−0.0003 (16)	−0.0064 (18)
C17	0.081 (3)	0.087 (3)	0.058 (2)	0.010 (3)	0.0235 (18)	0.015 (2)
C18	0.090 (3)	0.098 (3)	0.0375 (17)	0.013 (3)	0.0002 (16)	0.006 (2)
C19	0.0388 (19)	0.085 (3)	0.066 (2)	0.002 (2)	0.0081 (16)	−0.025 (2)
C20	0.116 (3)	0.141 (5)	0.062 (2)	0.019 (3)	0.047 (2)	0.022 (3)
C21	0.155 (5)	0.084 (3)	0.153 (5)	−0.012 (4)	0.076 (4)	0.010 (3)
C22	0.060 (3)	0.114 (4)	0.106 (3)	−0.005 (3)	0.005 (2)	−0.012 (3)
C23	0.056 (2)	0.072 (3)	0.059 (2)	0.017 (2)	0.0045 (17)	−0.0031 (19)

Geometric parameters (Å, º) top

C1—C18	1.508 (5)	C11—C14	1.364 (5)
C1—C16	1.520 (4)	C11—H11	0.9300
C1—H1A	0.9700	C12—C23	1.386 (4)
C1—H1B	0.9700	C12—H12	0.9300
P1—O2	1.463 (2)	C13—C17	1.521 (5)
P1—O1	1.5795 (19)	C13—C18	1.539 (4)
P1—N1	1.645 (2)	C13—H13	0.9800
P1—C2	1.792 (3)	C14—H14	0.9300
C2—C12	1.376 (4)	C15—C19	1.378 (5)
C2—C8	1.386 (4)	C15—H15	0.9300
C3—C9	1.380 (4)	C16—C22	1.533 (5)
C3—C5	1.380 (4)	C16—H16	0.9800
C3—N1	1.419 (3)	C17—C21	1.490 (7)
O1—C10	1.463 (3)	C17—C20	1.524 (5)
C4—C11	1.372 (5)	C17—H17	0.9800
C4—C5	1.382 (4)	C18—H18A	0.9700
C4—H4	0.9300	C18—H18B	0.9700
C5—H5	0.9300	C19—C23	1.358 (5)
N1—H6	0.8600	C19—H19	0.9300
C7—C10	1.507 (4)	C20—H20A	0.9600
C7—C16	1.530 (4)	C20—H20B	0.9600
C7—H7A	0.9700	C20—H20C	0.9600
C7—H7B	0.9700	C21—H21A	0.9600
C8—C15	1.390 (4)	C21—H21B	0.9600
C8—H8	0.9300	C21—H21C	0.9600
C9—C14	1.388 (4)	C22—H22A	0.9600
C9—H9	0.9300	C22—H22B	0.9600
C10—C13	1.523 (4)	C22—H22C	0.9600
C10—H10	0.9800	C23—H23	0.9300

C18—C1—C16	112.6 (3)	C17—C13—C18	117.0 (3)
C18—C1—H1A	109.1	C10—C13—C18	106.7 (2)
C16—C1—H1A	109.1	C17—C13—H13	105.8
C18—C1—H1B	109.1	C10—C13—H13	105.8
C16—C1—H1B	109.1	C18—C13—H13	105.8
H1A—C1—H1B	107.8	C11—C14—C9	120.6 (3)
O2—P1—O1	114.83 (11)	C11—C14—H14	119.7
O2—P1—N1	114.34 (11)	C9—C14—H14	119.7
O1—P1—N1	102.61 (11)	C19—C15—C8	120.3 (3)
O2—P1—C2	112.65 (14)	C19—C15—H15	119.9
O1—P1—C2	103.04 (11)	C8—C15—H15	119.9
N1—P1—C2	108.29 (14)	C1—C16—C7	109.5 (3)
C12—C2—C8	119.1 (3)	C1—C16—C22	112.0 (3)
C12—C2—P1	121.5 (2)	C7—C16—C22	110.7 (3)
C8—C2—P1	119.3 (2)	C1—C16—H16	108.2
C9—C3—C5	119.9 (2)	C7—C16—H16	108.2
C9—C3—N1	118.5 (3)	C22—C16—H16	108.2
C5—C3—N1	121.6 (3)	C21—C17—C20	110.6 (4)
C10—O1—P1	120.25 (16)	C21—C17—C13	113.4 (4)
C11—C4—C5	120.4 (3)	C20—C17—C13	112.4 (4)
C11—C4—H4	119.8	C21—C17—H17	106.6
C5—C4—H4	119.8	C20—C17—H17	106.6
C3—C5—C4	119.7 (3)	C13—C17—H17	106.6
C3—C5—H5	120.1	C1—C18—C13	112.1 (3)
C4—C5—H5	120.1	C1—C18—H18A	109.2
C3—N1—P1	126.9 (2)	C13—C18—H18A	109.2
C3—N1—H6	116.5	C1—C18—H18B	109.2
P1—N1—H6	116.5	C13—C18—H18B	109.2
C10—C7—C16	112.4 (3)	H18A—C18—H18B	107.9
C10—C7—H7A	109.1	C23—C19—C15	119.7 (3)
C16—C7—H7A	109.1	C23—C19—H19	120.2
C10—C7—H7B	109.1	C15—C19—H19	120.2
C16—C7—H7B	109.1	C17—C20—H20A	109.5
H7A—C7—H7B	107.9	C17—C20—H20B	109.5
C2—C8—C15	119.9 (3)	H20A—C20—H20B	109.5
C2—C8—H8	120.1	C17—C20—H20C	109.5
C15—C8—H8	120.1	H20A—C20—H20C	109.5
C3—C9—C14	119.5 (3)	H20B—C20—H20C	109.5
C3—C9—H9	120.2	C17—C21—H21A	109.5
C14—C9—H9	120.2	C17—C21—H21B	109.5
O1—C10—C7	110.6 (2)	H21A—C21—H21B	109.5
O1—C10—C13	107.8 (2)	C17—C21—H21C	109.5
C7—C10—C13	111.6 (2)	H21A—C21—H21C	109.5
O1—C10—H10	108.9	H21B—C21—H21C	109.5
C7—C10—H10	108.9	C16—C22—H22A	109.5
C13—C10—H10	108.9	C16—C22—H22B	109.5
C14—C11—C4	119.8 (3)	H22A—C22—H22B	109.5
C14—C11—H11	120.1	C16—C22—H22C	109.5
C4—C11—H11	120.1	H22A—C22—H22C	109.5
C2—C12—C23	120.4 (3)	H22B—C22—H22C	109.5
C2—C12—H12	119.8	C19—C23—C12	120.7 (3)
C23—C12—H12	119.8	C19—C23—H23	119.7
C17—C13—C10	114.8 (3)	C12—C23—H23	119.7

O2—P1—C2—C12	134.9 (2)	C5—C4—C11—C14	0.9 (5)
O1—P1—C2—C12	−100.8 (2)	C8—C2—C12—C23	−0.5 (4)
N1—P1—C2—C12	7.4 (3)	P1—C2—C12—C23	−177.7 (2)
O2—P1—C2—C8	−42.3 (3)	O1—C10—C13—C17	−47.9 (4)
O1—P1—C2—C8	82.0 (2)	C7—C10—C13—C17	−169.6 (3)
N1—P1—C2—C8	−169.8 (2)	O1—C10—C13—C18	−179.3 (3)
O2—P1—O1—C10	−27.3 (2)	C7—C10—C13—C18	59.1 (3)
N1—P1—O1—C10	97.4 (2)	C4—C11—C14—C9	−0.5 (5)
C2—P1—O1—C10	−150.1 (2)	C3—C9—C14—C11	−0.4 (5)
C9—C3—C5—C4	−0.4 (4)	C2—C8—C15—C19	−1.1 (5)
N1—C3—C5—C4	179.4 (3)	C18—C1—C16—C7	−52.1 (5)
C11—C4—C5—C3	−0.5 (5)	C18—C1—C16—C22	−175.3 (3)
C9—C3—N1—P1	167.3 (2)	C10—C7—C16—C1	53.0 (4)
C5—C3—N1—P1	−12.5 (4)	C10—C7—C16—C22	177.0 (3)
O2—P1—N1—C3	−45.0 (3)	C10—C13—C17—C21	−62.8 (5)
O1—P1—N1—C3	−170.0 (2)	C18—C13—C17—C21	63.4 (5)
C2—P1—N1—C3	81.5 (2)	C10—C13—C17—C20	170.8 (3)
C12—C2—C8—C15	1.0 (4)	C18—C13—C17—C20	−63.0 (5)
P1—C2—C8—C15	178.2 (2)	C16—C1—C18—C13	57.0 (5)
C5—C3—C9—C14	0.8 (4)	C17—C13—C18—C1	171.6 (3)
N1—C3—C9—C14	−179.0 (3)	C10—C13—C18—C1	−58.3 (4)
P1—O1—C10—C7	−81.0 (3)	C8—C15—C19—C23	0.7 (5)
P1—O1—C10—C13	156.7 (2)	C15—C19—C23—C12	−0.2 (5)
C16—C7—C10—O1	−178.9 (2)	C2—C12—C23—C19	0.1 (5)
C16—C7—C10—C13	−58.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H6···O2ⁱ	0.86	2.24	3.053 (3)	157

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₃₀NO₂P
M_r	371.44
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	8.6934 (8), 5.4716 (5), 22.100 (2)
β (°)	101.006 (1)
V (Å³)	1031.90 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.45 × 0.36 × 0.17

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.936, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	5183, 3589, 2814
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.104, 1.09
No. of reflections	3589
No. of parameters	238
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.25
Absolute structure	Flack (1983), 1550 Friedel pairs
Absolute structure parameter	−0.06 (12)

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
N1—H6···O2ⁱ	0.86	2.24	3.053 (3)	157

Symmetry code: (i) x, y−1, z.

Acknowledgements

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

References

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