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

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

doi:10.1107/S1600536811012864

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1244

doi:10.1107/S1600536811012864

Open

access

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

Li-Juan Liu,^a Fan-Jie Meng,^a Hao Xu,^a Daqi Wang ^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 3 April 2011; accepted 6 April 2011; online 29 April 2011)

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

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
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536811012864/cv5071sup1.cif

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

checkCIF report

Comment top

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].

Related literature top

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

Experimental top

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.

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 30% probability displacement ellipsoids. H atoms have been omitted for clarity.

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

Crystal data top

C₂₀H₃₄NO₂P	F(000) = 768
M_r = 351.45	D_x = 1.126 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1474 reflections
a = 8.305 (3) Å	θ = 2.6–18.0°
b = 11.064 (4) Å	µ = 0.14 mm⁻¹
c = 22.557 (9) Å	T = 298 K
V = 2072.8 (15) Å³	Block, colourless
Z = 4	0.45 × 0.40 × 0.37 mm

Data collection top

Bruker SMART-1000 CCD area-detector diffractometer	3610 independent reflections
Radiation source: fine-focus sealed tube	1993 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.938, T_max = 0.949	k = −10→13
10336 measured reflections	l = −26→25

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) = 0.130	w = 1/[σ²(F_o²) + (0.0457P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3610 reflections	Δρ_max = 0.27 e Å⁻³
223 parameters	Δρ_min = −0.31 e Å⁻³
114 restraints	Absolute structure: Flack (1983), 2085 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (17)

Crystal data top

C₂₀H₃₄NO₂P	V = 2072.8 (15) Å³
M_r = 351.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.305 (3) Å	µ = 0.14 mm⁻¹
b = 11.064 (4) Å	T = 298 K
c = 22.557 (9) Å	0.45 × 0.40 × 0.37 mm

Data collection top

Bruker SMART-1000 CCD area-detector diffractometer	3610 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1993 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.949	R_int = 0.075
10336 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.130	Δρ_max = 0.27 e Å⁻³
S = 1.02	Δρ_min = −0.31 e Å⁻³
3610 reflections	Absolute structure: Flack (1983), 2085 Friedel pairs
223 parameters	Absolute structure parameter: 0.06 (17)
114 restraints

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
P1	0.54415 (14)	0.34918 (10)	0.23972 (5)	0.0462 (3)
O1	0.6726 (3)	0.2945 (3)	0.19552 (12)	0.0503 (8)
O2	0.5009 (3)	0.4756 (2)	0.23040 (13)	0.0578 (9)
N1	0.3903 (4)	0.2570 (3)	0.23664 (16)	0.0521 (9)
H1	0.4139	0.1816	0.2332	0.063*
C4	0.7421 (5)	0.3383 (5)	0.09282 (17)	0.0586 (13)
H4	0.8542	0.3192	0.1027	0.070*
C5	0.6512 (5)	0.3284 (4)	0.30808 (17)	0.0418 (11)
C6	0.7238 (7)	0.4734 (5)	0.1000 (2)	0.0679 (14)
H6	0.7301	0.4912	0.1425	0.082*
C7	0.6383 (5)	0.2641 (4)	0.13399 (18)	0.0511 (12)
H7	0.5247	0.2806	0.1256	0.061*
C8	0.6923 (6)	0.4277 (4)	0.3410 (2)	0.0624 (14)
H8	0.6632	0.5044	0.3281	0.075*
C9	0.6699 (6)	0.1301 (4)	0.1270 (2)	0.0636 (14)
H9A	0.7795	0.1132	0.1394	0.076*
H9B	0.5983	0.0861	0.1533	0.076*
C10	0.2175 (5)	0.2851 (4)	0.2390 (2)	0.0605 (12)
C11	0.6471 (7)	0.0842 (5)	0.0651 (2)	0.0708 (15)
H11	0.5336	0.0970	0.0551	0.085*
C12	0.7434 (7)	0.1585 (6)	0.0229 (2)	0.0831 (17)
H12A	0.7165	0.1348	−0.0173	0.100*
H12B	0.8568	0.1418	0.0291	0.100*
C13	0.6942 (6)	0.2165 (4)	0.3286 (2)	0.0627 (14)
H13	0.6688	0.1482	0.3065	0.075*
C14	0.7741 (6)	0.2041 (5)	0.3811 (2)	0.0750 (16)
H14	0.7992	0.1275	0.3952	0.090*
C15	0.8169 (6)	0.3034 (6)	0.4129 (2)	0.0723 (16)
H15	0.8739	0.2941	0.4481	0.087*
C16	0.7145 (6)	0.2930 (5)	0.0299 (2)	0.0732 (16)
H16A	0.6046	0.3111	0.0183	0.088*
H16B	0.7856	0.3362	0.0032	0.088*
C17	0.1234 (6)	0.1719 (5)	0.2447 (3)	0.1004 (18)
H17A	0.1550	0.1304	0.2802	0.151*
H17B	0.1435	0.1211	0.2110	0.151*
H17C	0.0107	0.1908	0.2467	0.151*
C18	0.6792 (8)	−0.0509 (5)	0.0587 (2)	0.103 (2)
H18A	0.6648	−0.0744	0.0181	0.154*
H18B	0.6054	−0.0951	0.0833	0.154*
H18C	0.7876	−0.0683	0.0708	0.154*
C19	0.5637 (7)	0.5245 (5)	0.0774 (2)	0.0915 (19)
H19A	0.5523	0.5065	0.0360	0.137*
H19B	0.5621	0.6105	0.0830	0.137*
H19C	0.4764	0.4885	0.0990	0.137*
C20	0.7781 (7)	0.4143 (5)	0.3941 (2)	0.0723 (16)
H20	0.8077	0.4819	0.4160	0.087*
C21	0.8611 (8)	0.5424 (6)	0.0696 (3)	0.109 (2)
H21A	0.9626	0.5089	0.0817	0.163*
H21B	0.8566	0.6261	0.0807	0.163*
H21C	0.8502	0.5354	0.0274	0.163*
C22	0.1788 (8)	0.3622 (6)	0.2900 (3)	0.136 (2)
H22A	0.0641	0.3665	0.2948	0.204*
H22B	0.2210	0.4419	0.2835	0.204*
H22C	0.2260	0.3286	0.3252	0.204*
C23	0.1671 (8)	0.3533 (7)	0.1851 (3)	0.137 (2)
H23A	0.0565	0.3770	0.1890	0.206*
H23B	0.1793	0.3028	0.1508	0.206*
H23C	0.2332	0.4240	0.1809	0.206*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0430 (6)	0.0520 (7)	0.0436 (7)	−0.0011 (6)	−0.0006 (6)	0.0021 (6)
O1	0.0398 (17)	0.071 (2)	0.0398 (17)	−0.0001 (16)	−0.0011 (14)	−0.0013 (14)
O2	0.054 (2)	0.0493 (18)	0.070 (2)	−0.0005 (15)	−0.0028 (16)	0.0074 (15)
N1	0.037 (2)	0.052 (2)	0.068 (2)	−0.0012 (17)	0.0005 (19)	−0.0009 (19)
C4	0.042 (3)	0.093 (4)	0.041 (3)	0.000 (3)	−0.004 (2)	0.006 (3)
C5	0.040 (3)	0.051 (3)	0.035 (2)	−0.003 (2)	−0.0010 (19)	0.005 (2)
C6	0.067 (4)	0.075 (4)	0.062 (3)	−0.014 (3)	0.004 (3)	0.001 (3)
C7	0.040 (3)	0.076 (4)	0.038 (3)	−0.002 (3)	0.003 (2)	−0.009 (2)
C8	0.077 (4)	0.057 (3)	0.053 (3)	0.008 (3)	−0.009 (3)	−0.005 (3)
C9	0.053 (3)	0.080 (4)	0.058 (3)	0.005 (3)	0.003 (2)	−0.005 (3)
C10	0.042 (3)	0.065 (3)	0.074 (3)	−0.004 (2)	0.001 (3)	−0.003 (3)
C11	0.065 (4)	0.090 (4)	0.057 (3)	0.004 (3)	0.001 (3)	−0.011 (3)
C12	0.078 (4)	0.115 (5)	0.056 (3)	0.008 (4)	0.008 (3)	−0.014 (3)
C13	0.074 (4)	0.050 (3)	0.064 (3)	0.001 (3)	−0.017 (3)	−0.002 (2)
C14	0.076 (4)	0.076 (4)	0.073 (4)	−0.001 (3)	−0.028 (3)	0.010 (3)
C15	0.067 (4)	0.101 (5)	0.048 (3)	0.004 (3)	−0.019 (3)	0.002 (3)
C16	0.072 (4)	0.104 (5)	0.044 (3)	−0.003 (3)	0.002 (3)	0.001 (3)
C17	0.055 (3)	0.079 (4)	0.168 (5)	−0.013 (3)	0.010 (4)	−0.014 (4)
C18	0.120 (6)	0.098 (5)	0.090 (4)	0.020 (4)	−0.006 (4)	−0.037 (3)
C19	0.097 (5)	0.084 (4)	0.093 (4)	−0.006 (4)	0.017 (4)	0.014 (3)
C20	0.093 (5)	0.064 (4)	0.059 (4)	−0.002 (4)	−0.018 (3)	−0.016 (3)
C21	0.098 (5)	0.118 (5)	0.110 (5)	−0.046 (4)	0.018 (4)	0.020 (4)
C22	0.081 (4)	0.143 (5)	0.183 (6)	−0.013 (4)	0.033 (4)	−0.072 (5)
C23	0.074 (4)	0.166 (6)	0.172 (6)	−0.017 (4)	−0.036 (4)	0.072 (5)

Geometric parameters (Å, º) top

P1—O2	1.459 (3)	C12—H12A	0.9700
P1—O1	1.581 (3)	C12—H12B	0.9700
P1—N1	1.636 (3)	C13—C14	1.365 (6)
P1—C5	1.794 (4)	C13—H13	0.9300
O1—C7	1.456 (5)	C14—C15	1.359 (6)
N1—C10	1.470 (5)	C14—H14	0.9300
N1—H1	0.8600	C15—C20	1.338 (6)
C4—C7	1.510 (6)	C15—H15	0.9300
C4—C6	1.512 (6)	C16—H16A	0.9700
C4—C16	1.524 (6)	C16—H16B	0.9700
C4—H4	0.9800	C17—H17A	0.9600
C5—C13	1.369 (6)	C17—H17B	0.9600
C5—C8	1.370 (6)	C17—H17C	0.9600
C6—C19	1.533 (7)	C18—H18A	0.9600
C6—C21	1.534 (7)	C18—H18B	0.9600
C6—H6	0.9800	C18—H18C	0.9600
C7—C9	1.514 (6)	C19—H19A	0.9600
C7—H7	0.9800	C19—H19B	0.9600
C8—C20	1.400 (6)	C19—H19C	0.9600
C8—H8	0.9300	C20—H20	0.9300
C9—C11	1.497 (6)	C21—H21A	0.9600
C9—H9A	0.9700	C21—H21B	0.9600
C9—H9B	0.9700	C21—H21C	0.9600
C10—C22	1.469 (7)	C22—H22A	0.9600
C10—C17	1.483 (6)	C22—H22B	0.9600
C10—C23	1.490 (7)	C22—H22C	0.9600
C11—C12	1.490 (7)	C23—H23A	0.9600
C11—C18	1.525 (7)	C23—H23B	0.9600
C11—H11	0.9800	C23—H23C	0.9600
C12—C16	1.516 (7)

O2—P1—O1	116.25 (17)	C16—C12—H12B	109.0
O2—P1—N1	113.53 (18)	H12A—C12—H12B	107.8
O1—P1—N1	105.14 (17)	C5—C13—C14	120.7 (4)
O2—P1—C5	111.6 (2)	C5—C13—H13	119.6
O1—P1—C5	99.14 (18)	C14—C13—H13	119.6
N1—P1—C5	110.08 (19)	C15—C14—C13	120.3 (5)
C7—O1—P1	123.9 (3)	C15—C14—H14	119.9
C10—N1—P1	129.0 (3)	C13—C14—H14	119.9
C10—N1—H1	115.5	C20—C15—C14	120.7 (5)
P1—N1—H1	115.5	C20—C15—H15	119.7
C7—C4—C6	114.5 (4)	C14—C15—H15	119.7
C7—C4—C16	108.0 (4)	C12—C16—C4	113.3 (4)
C6—C4—C16	114.2 (4)	C12—C16—H16A	108.9
C7—C4—H4	106.5	C4—C16—H16A	108.9
C6—C4—H4	106.5	C12—C16—H16B	108.9
C16—C4—H4	106.5	C4—C16—H16B	108.9
C13—C5—C8	118.5 (4)	H16A—C16—H16B	107.7
C13—C5—P1	122.4 (4)	C10—C17—H17A	109.5
C8—C5—P1	119.2 (4)	C10—C17—H17B	109.5
C4—C6—C19	114.6 (4)	H17A—C17—H17B	109.5
C4—C6—C21	111.6 (5)	C10—C17—H17C	109.5
C19—C6—C21	108.2 (4)	H17A—C17—H17C	109.5
C4—C6—H6	107.4	H17B—C17—H17C	109.5
C19—C6—H6	107.4	C11—C18—H18A	109.5
C21—C6—H6	107.4	C11—C18—H18B	109.5
O1—C7—C4	110.4 (4)	H18A—C18—H18B	109.5
O1—C7—C9	107.0 (3)	C11—C18—H18C	109.5
C4—C7—C9	111.7 (4)	H18A—C18—H18C	109.5
O1—C7—H7	109.2	H18B—C18—H18C	109.5
C4—C7—H7	109.2	C6—C19—H19A	109.5
C9—C7—H7	109.2	C6—C19—H19B	109.5
C5—C8—C20	120.4 (5)	H19A—C19—H19B	109.5
C5—C8—H8	119.8	C6—C19—H19C	109.5
C20—C8—H8	119.8	H19A—C19—H19C	109.5
C11—C9—C7	114.0 (4)	H19B—C19—H19C	109.5
C11—C9—H9A	108.7	C15—C20—C8	119.4 (5)
C7—C9—H9A	108.7	C15—C20—H20	120.3
C11—C9—H9B	108.7	C8—C20—H20	120.3
C7—C9—H9B	108.7	C6—C21—H21A	109.5
H9A—C9—H9B	107.6	C6—C21—H21B	109.5
N1—C10—C22	111.4 (4)	H21A—C21—H21B	109.5
N1—C10—C17	109.8 (4)	C6—C21—H21C	109.5
C22—C10—C17	107.8 (5)	H21A—C21—H21C	109.5
N1—C10—C23	110.6 (4)	H21B—C21—H21C	109.5
C22—C10—C23	106.5 (5)	C10—C22—H22A	109.5
C17—C10—C23	110.6 (5)	C10—C22—H22B	109.5
C12—C11—C9	109.9 (4)	H22A—C22—H22B	109.5
C12—C11—C18	112.7 (5)	C10—C22—H22C	109.5
C9—C11—C18	113.5 (4)	H22A—C22—H22C	109.5
C12—C11—H11	106.8	H22B—C22—H22C	109.5
C9—C11—H11	106.8	C10—C23—H23A	109.5
C18—C11—H11	106.8	C10—C23—H23B	109.5
C11—C12—C16	113.0 (4)	H23A—C23—H23B	109.5
C11—C12—H12A	109.0	C10—C23—H23C	109.5
C16—C12—H12A	109.0	H23A—C23—H23C	109.5
C11—C12—H12B	109.0	H23B—C23—H23C	109.5

O2—P1—O1—C7	−73.5 (3)	C16—C4—C7—C9	55.0 (5)
N1—P1—O1—C7	52.9 (3)	C13—C5—C8—C20	0.7 (7)
C5—P1—O1—C7	166.8 (3)	P1—C5—C8—C20	−179.0 (4)
O2—P1—N1—C10	−14.7 (5)	O1—C7—C9—C11	−177.5 (4)
O1—P1—N1—C10	−142.9 (4)	C4—C7—C9—C11	−56.6 (5)
C5—P1—N1—C10	111.2 (4)	P1—N1—C10—C22	−51.2 (6)
O2—P1—C5—C13	175.2 (4)	P1—N1—C10—C17	−170.6 (4)
O1—P1—C5—C13	−61.8 (4)	P1—N1—C10—C23	67.1 (6)
N1—P1—C5—C13	48.1 (4)	C7—C9—C11—C12	52.8 (6)
O2—P1—C5—C8	−5.2 (4)	C7—C9—C11—C18	−180.0 (5)
O1—P1—C5—C8	117.9 (4)	C9—C11—C12—C16	−51.2 (6)
N1—P1—C5—C8	−132.2 (3)	C18—C11—C12—C16	−178.9 (4)
C7—C4—C6—C19	−71.5 (5)	C8—C5—C13—C14	1.0 (7)
C16—C4—C6—C19	53.6 (6)	P1—C5—C13—C14	−179.3 (4)
C7—C4—C6—C21	165.0 (4)	C5—C13—C14—C15	−2.3 (8)
C16—C4—C6—C21	−69.8 (6)	C13—C14—C15—C20	1.7 (9)
P1—O1—C7—C4	118.4 (4)	C11—C12—C16—C4	54.8 (6)
P1—O1—C7—C9	−119.8 (3)	C7—C4—C16—C12	−54.9 (6)
C6—C4—C7—O1	−57.7 (5)	C6—C4—C16—C12	176.5 (4)
C16—C4—C7—O1	173.9 (4)	C14—C15—C20—C8	0.0 (9)
C6—C4—C7—C9	−176.6 (4)	C5—C8—C20—C15	−1.2 (8)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₃₄NO₂P
M_r	351.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	8.305 (3), 11.064 (4), 22.557 (9)
V (Å³)	2072.8 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.45 × 0.40 × 0.37

Data collection
Diffractometer	Bruker SMART1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.938, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	10336, 3610, 1993
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.130, 1.02
No. of reflections	3610
No. of parameters	223
No. of restraints	114
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.31
Absolute structure	Flack (1983), 2085 Friedel pairs
Absolute structure parameter	0.06 (17)

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
N1—H1···O2ⁱ	0.86	2.52	3.326 (4)	156
C13—H13···O2ⁱ	0.93	2.51	3.391 (5)	157

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

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
Chaloner, P. A., Harrison, R. M. & Hitchcock, P. B. (1991). Acta Cryst. C47, 2241–2242. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Meng, F.-J., Xu, H., Liu, L.-J., Wang, D. & Zhao, C.-Q. (2010). Acta Cryst. E66, o2352. Web of Science CSD 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