Diisopropyl [(benzoyl­amino)­(phen­yl)meth­yl]phospho­nate

Fang, H.; Fang, M.-J.; Xu, Y.; Yu, W.-C.; Zhao, Y.-F.

doi:10.1107/S1600536809006382

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o642

doi:10.1107/S1600536809006382

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Diisopropyl [(benzoylamino)(phenyl)methyl]phosphonate

Hua Fang,^a ^* Mei-Juan Fang,^b Ying Xu,^b Wen-Cheng Yu ^b and Yu-Fen Zhao ^c

^aThe Third Institute of Oceanography of the State Oceanic Administration, Xiamen 361005, People's Republic of China, ^bDepartment of Pharmaceutical Science, Medical College, Xiamen University, Xiamen 361005, People's Republic of China, and ^cDepartment of Chemistry, Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, People's Republic of China
^*Correspondence e-mail: fangmj@xmu.edu.cn

(Received 13 February 2009; accepted 21 February 2009; online 28 February 2009)

The title compound, C₂₀H₂₆NO₄P, has been obtained by the reaction of benzoyl chloride and diisopropyl[amino(phenyl)methyl]phosphonate. The dihedral angle between the planes of the benzoylamino group and the phenyl ring is 77.0 (2)°. The crystal structure is stabilized by strong intermolecular N—H⋯O hydrogen bonds between the doubly bonded phosphoryl O atom and the amide N atom which link the molecules into pairs about a center of symmetry.

Related literature

For the biological activity and pharmaceutical interest of α-hydroxyphosphonic acid esters, see: Stowasser et al. (1992 ); Chen et al. (1995 ). For their use as reagents in the synthesis of enol ethers and α-ketophosphonates, see: Babak & Rahman (2001 ). For the synthesis, see: Drescher et al. (1995 ). For bond lengths and angles in related compunds, see: Smaardijk et al. (1985 ).

Experimental

Crystal data

C₂₀H₂₆NO₄P
M_r = 375.39
Triclinic, $[P \overline 1]$
a = 10.839 (4) Å
b = 10.925 (5) Å
c = 11.057 (5) Å
α = 61.364 (8)°
β = 83.362 (8)°
γ = 60.470 (6)°
V = 987.3 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 273 K
0.28 × 0.21 × 0.05 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.956, T_max = 0.992
4991 measured reflections
3411 independent reflections
2509 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.174
S = 0.98
3411 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.05	2.895 (3)	165
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006382/fl2235sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006382/fl2235Isup2.hkl

checkCIF report

Comment top

In recent years α-hydroxyphosphonic acids esters have attracted much attention due to their wide biological activity (Stowasser et al., 1992) and pharmaceutical interest (Chen et al., 1995). They are useful reagents for the synthesis of enol ethers and α-ketophosphonates (Babak et al., 2001). Bond lengths and angles in the title compound, (I), are in agreement with the values reported for related compounds (Smaardijk et al., 1985). The dihedral angle between the planes of the benzoylamino group and phenyl ring is 103.0 (2)° (Fig. 1). The amide N atom is involved in a hydrogen-bonding interaction with the phosphoryl O atom of a neighboring molecule linking the molecules into pairs around a centerof symmetry (Table 1 and Fig. 2).

Related literature top

For the biological activity and pharmaceutical interest of α-hydroxyphosphonic acid esters, see: Stowasser et al. (1992); Chen et al. (1995). For their use as reagents in the synthesis of enol ethers and α-ketophosphonates, see: Babak & Rahman (2001). For the synthesis, see: Drescher et al. (1995). For bond lengths and angles in related compunds, see: Smaardijk et al. (1985).

Experimental top

A solution of dry dichloromethane (20 ml) containing (amino-phenyl-methyl)-phosphonic acid diisopropyl ester (1 mmol, 0.27 g) and triethylamine (0.4 ml) was added dropwise to a solution of dichloromethane (10 ml) containing benzoyl chloride (1.2 mmol, 0.17 g). The reaction mixture was stirred for 6 h at room temperature and the solvent was then removed under reduced pressure to give a residue, which was extracted with ethyl acetate (3 × 15 ml). The solution was dried over anhydrous MgSO₄ and concentrated under vacuum to obtain a slurry residue, which was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 2:1) to give (I) as a colorless amorphous solid (Drescher, et al., 1995). Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of a petroleum ether /dichloromethane solution (1:1 v/v).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule showing the anisotropic displacement parameters of the non-hydrogen atoms at the 30% probability level. The H atoms are drawn as spheres of arbitrary radii.
	Fig. 2. Packing diagram of title compound, showing the N—H···O hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonding have been omitted. [Symmetry code: (i) -x + 1, -y + 2, -z + 1)].
	Fig. 3. The formation of the title compound.

Diisopropyl [(benzoylamino)(phenyl)methyl]phosphonate top

Crystal data top

C₂₀H₂₆NO₄P	Z = 2
M_r = 375.39	F(000) = 400
Triclinic, P1	D_x = 1.263 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.839 (4) Å	Cell parameters from 1689 reflections
b = 10.925 (5) Å	θ = 2.3–27.7°
c = 11.057 (5) Å	µ = 0.16 mm⁻¹
α = 61.364 (8)°	T = 273 K
β = 83.362 (8)°	Chunk, colorless
γ = 60.470 (6)°	0.28 × 0.21 × 0.05 mm
V = 987.3 (7) Å³

Data collection top

Bruker APEX area-detector diffractometer	3411 independent reflections
Radiation source: fine-focus sealed tube	2509 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
T_min = 0.956, T_max = 0.992	k = −12→12
4991 measured reflections	l = −10→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.174	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.097P)²] where P = (F_o² + 2F_c²)/3
3411 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₀H₂₆NO₄P	γ = 60.470 (6)°
M_r = 375.39	V = 987.3 (7) Å³
Triclinic, P1	Z = 2
a = 10.839 (4) Å	Mo Kα radiation
b = 10.925 (5) Å	µ = 0.16 mm⁻¹
c = 11.057 (5) Å	T = 273 K
α = 61.364 (8)°	0.28 × 0.21 × 0.05 mm
β = 83.362 (8)°

Data collection top

Bruker APEX area-detector diffractometer	3411 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2509 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.992	R_int = 0.042
4991 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.174	H-atom parameters constrained
S = 0.98	Δρ_max = 0.60 e Å⁻³
3411 reflections	Δρ_min = −0.44 e Å⁻³
235 parameters

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	0.73254 (8)	0.85680 (9)	0.47527 (8)	0.0311 (3)
N1	0.6453 (2)	0.6827 (3)	0.6988 (3)	0.0310 (6)
H1A	0.5566	0.7577	0.6718	0.037*
O1	0.8049 (2)	0.4184 (2)	0.8105 (3)	0.0546 (7)
C1	0.6797 (3)	0.5282 (4)	0.7762 (3)	0.0339 (7)
O2	0.6331 (2)	1.0278 (2)	0.4252 (2)	0.0412 (6)
C2	0.5598 (3)	0.4933 (3)	0.8226 (3)	0.0336 (7)
O3	0.6811 (2)	0.7980 (2)	0.3986 (2)	0.0400 (6)
C3	0.5965 (4)	0.3371 (4)	0.9147 (4)	0.0505 (9)
H3A	0.6928	0.2572	0.9424	0.061*
O4	0.8922 (2)	0.8119 (2)	0.4564 (2)	0.0401 (6)
C4	0.4921 (4)	0.2969 (5)	0.9671 (4)	0.0602 (11)
H4A	0.5182	0.1906	1.0313	0.072*
C5	0.3507 (4)	0.4130 (5)	0.9247 (4)	0.0514 (9)
H5A	0.2804	0.3859	0.9603	0.062*
C6	0.3123 (4)	0.5681 (4)	0.8304 (4)	0.0549 (10)
H6A	0.2158	0.6472	0.8006	0.066*
C7	0.4171 (3)	0.6079 (4)	0.7792 (4)	0.0505 (9)
H7A	0.3905	0.7142	0.7142	0.061*
C8	0.7582 (3)	0.7231 (3)	0.6607 (3)	0.0305 (7)
H8A	0.8470	0.6220	0.6812	0.037*
C9	0.7819 (3)	0.7826 (3)	0.7489 (3)	0.0307 (7)
C10	0.6722 (3)	0.9170 (4)	0.7536 (3)	0.0431 (8)
H10A	0.5844	0.9768	0.6961	0.052*
C11	0.6917 (4)	0.9627 (4)	0.8423 (4)	0.0531 (9)
H11A	0.6166	1.0523	0.8456	0.064*
C12	0.8210 (4)	0.8774 (5)	0.9261 (4)	0.0562 (10)
H12A	0.8336	0.9095	0.9856	0.067*
C13	0.9309 (4)	0.7456 (5)	0.9221 (4)	0.0526 (9)
H13A	1.0191	0.6879	0.9784	0.063*
C14	0.9111 (3)	0.6979 (4)	0.8344 (3)	0.0398 (8)
H14A	0.9862	0.6070	0.8329	0.048*
C15	0.7424 (4)	0.6316 (4)	0.4291 (4)	0.0435 (8)
H15A	0.7990	0.5581	0.5230	0.052*
C16	0.6184 (4)	0.6079 (5)	0.4248 (4)	0.0608 (10)
H16A	0.5615	0.6255	0.4942	0.091*
H16B	0.6538	0.5000	0.4432	0.091*
H16C	0.5604	0.6832	0.3342	0.091*
C17	0.8383 (4)	0.6056 (5)	0.3243 (4)	0.0635 (11)
H17A	0.9161	0.6209	0.3328	0.095*
H17B	0.7841	0.6815	0.2319	0.095*
H17C	0.8758	0.4979	0.3409	0.095*
C18	0.9332 (4)	0.9289 (4)	0.3580 (4)	0.0458 (8)
H18A	0.8731	1.0307	0.3593	0.055*
C19	0.9101 (5)	0.9581 (6)	0.2149 (4)	0.0810 (14)
H19A	0.8101	1.0015	0.1875	0.121*
H19B	0.9658	0.8583	0.2131	0.121*
H19C	0.9393	1.0334	0.1513	0.121*
C20	1.0845 (4)	0.8639 (6)	0.4093 (5)	0.0816 (14)
H20A	1.0916	0.8510	0.5009	0.122*
H20B	1.1162	0.9373	0.3470	0.122*
H20C	1.1438	0.7612	0.4133	0.122*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0254 (4)	0.0278 (5)	0.0360 (5)	−0.0115 (3)	0.0062 (3)	−0.0149 (4)
N1	0.0210 (12)	0.0262 (13)	0.0398 (14)	−0.0105 (10)	0.0066 (11)	−0.0139 (12)
O1	0.0308 (12)	0.0297 (13)	0.0752 (18)	−0.0100 (10)	0.0017 (12)	−0.0102 (13)
C1	0.0348 (17)	0.0299 (17)	0.0363 (17)	−0.0170 (14)	0.0064 (14)	−0.0150 (15)
O2	0.0342 (11)	0.0288 (12)	0.0497 (13)	−0.0118 (9)	0.0050 (10)	−0.0155 (11)
C2	0.0407 (17)	0.0328 (17)	0.0343 (17)	−0.0228 (15)	0.0099 (14)	−0.0176 (15)
O3	0.0379 (12)	0.0357 (12)	0.0442 (12)	−0.0141 (10)	0.0030 (10)	−0.0217 (11)
C3	0.049 (2)	0.036 (2)	0.054 (2)	−0.0231 (17)	0.0061 (18)	−0.0111 (18)
O4	0.0284 (11)	0.0367 (12)	0.0448 (13)	−0.0162 (10)	0.0120 (10)	−0.0142 (11)
C4	0.075 (3)	0.050 (2)	0.055 (2)	−0.046 (2)	0.011 (2)	−0.011 (2)
C5	0.059 (2)	0.073 (3)	0.052 (2)	−0.051 (2)	0.0245 (19)	−0.035 (2)
C6	0.0391 (19)	0.055 (2)	0.077 (3)	−0.0298 (18)	0.0200 (19)	−0.032 (2)
C7	0.0383 (18)	0.0377 (19)	0.070 (2)	−0.0226 (16)	0.0128 (18)	−0.0197 (19)
C8	0.0236 (14)	0.0258 (16)	0.0400 (17)	−0.0107 (12)	0.0052 (13)	−0.0164 (15)
C9	0.0266 (15)	0.0321 (17)	0.0336 (16)	−0.0164 (13)	0.0097 (13)	−0.0155 (15)
C10	0.0386 (18)	0.0392 (19)	0.0472 (19)	−0.0152 (15)	0.0013 (16)	−0.0216 (17)
C11	0.057 (2)	0.050 (2)	0.059 (2)	−0.0245 (19)	0.012 (2)	−0.035 (2)
C12	0.080 (3)	0.068 (3)	0.052 (2)	−0.053 (2)	0.019 (2)	−0.036 (2)
C13	0.052 (2)	0.066 (2)	0.044 (2)	−0.040 (2)	0.0010 (18)	−0.018 (2)
C14	0.0338 (17)	0.0424 (19)	0.0400 (17)	−0.0211 (15)	0.0077 (15)	−0.0163 (16)
C15	0.0454 (19)	0.0363 (18)	0.048 (2)	−0.0177 (15)	0.0026 (17)	−0.0213 (17)
C16	0.064 (2)	0.068 (3)	0.072 (3)	−0.041 (2)	0.019 (2)	−0.043 (2)
C17	0.058 (2)	0.068 (3)	0.082 (3)	−0.033 (2)	0.033 (2)	−0.052 (3)
C18	0.0456 (19)	0.044 (2)	0.049 (2)	−0.0285 (17)	0.0128 (17)	−0.0182 (18)
C19	0.095 (3)	0.108 (4)	0.050 (2)	−0.073 (3)	0.020 (2)	−0.023 (3)
C20	0.063 (3)	0.094 (3)	0.074 (3)	−0.056 (3)	0.006 (2)	−0.013 (3)

Geometric parameters (Å, º) top

P1—O2	1.456 (2)	C10—H10A	0.9300
P1—O3	1.559 (2)	C11—C12	1.369 (5)
P1—O4	1.567 (2)	C11—H11A	0.9300
P1—C8	1.809 (3)	C12—C13	1.361 (5)
N1—C1	1.337 (4)	C12—H12A	0.9300
N1—C8	1.451 (4)	C13—C14	1.379 (5)
N1—H1A	0.8600	C13—H13A	0.9300
O1—C1	1.226 (3)	C14—H14A	0.9300
C1—C2	1.498 (4)	C15—C16	1.498 (5)
C2—C3	1.365 (4)	C15—C17	1.500 (5)
C2—C7	1.370 (4)	C15—H15A	0.9800
O3—C15	1.460 (4)	C16—H16A	0.9600
C3—C4	1.380 (5)	C16—H16B	0.9600
C3—H3A	0.9300	C16—H16C	0.9600
O4—C18	1.460 (4)	C17—H17A	0.9600
C4—C5	1.363 (5)	C17—H17B	0.9600
C4—H4A	0.9300	C17—H17C	0.9600
C5—C6	1.358 (5)	C18—C20	1.482 (5)
C5—H5A	0.9300	C18—C19	1.483 (5)
C6—C7	1.380 (5)	C18—H18A	0.9800
C6—H6A	0.9300	C19—H19A	0.9600
C7—H7A	0.9300	C19—H19B	0.9600
C8—C9	1.507 (4)	C19—H19C	0.9600
C8—H8A	0.9800	C20—H20A	0.9600
C9—C14	1.378 (4)	C20—H20B	0.9600
C9—C10	1.382 (4)	C20—H20C	0.9600
C10—C11	1.370 (4)

O2—P1—O3	109.31 (12)	C10—C11—H11A	119.7
O2—P1—O4	114.66 (12)	C13—C12—C11	119.9 (3)
O3—P1—O4	108.59 (12)	C13—C12—H12A	120.0
O2—P1—C8	116.66 (13)	C11—C12—H12A	120.0
O3—P1—C8	107.29 (13)	C12—C13—C14	119.7 (3)
O4—P1—C8	99.67 (12)	C12—C13—H13A	120.1
C1—N1—C8	119.7 (2)	C14—C13—H13A	120.1
C1—N1—H1A	120.1	C9—C14—C13	121.2 (3)
C8—N1—H1A	120.1	C9—C14—H14A	119.4
O1—C1—N1	121.6 (3)	C13—C14—H14A	119.4
O1—C1—C2	120.7 (3)	O3—C15—C16	106.6 (3)
N1—C1—C2	117.7 (3)	O3—C15—C17	108.8 (3)
C3—C2—C7	118.6 (3)	C16—C15—C17	113.3 (3)
C3—C2—C1	117.3 (3)	O3—C15—H15A	109.4
C7—C2—C1	124.1 (3)	C16—C15—H15A	109.4
C15—O3—P1	126.33 (19)	C17—C15—H15A	109.4
C2—C3—C4	120.6 (3)	C15—C16—H16A	109.5
C2—C3—H3A	119.7	C15—C16—H16B	109.5
C4—C3—H3A	119.7	H16A—C16—H16B	109.5
C18—O4—P1	123.20 (19)	C15—C16—H16C	109.5
C5—C4—C3	120.0 (3)	H16A—C16—H16C	109.5
C5—C4—H4A	120.0	H16B—C16—H16C	109.5
C3—C4—H4A	120.0	C15—C17—H17A	109.5
C6—C5—C4	120.1 (3)	C15—C17—H17B	109.5
C6—C5—H5A	119.9	H17A—C17—H17B	109.5
C4—C5—H5A	119.9	C15—C17—H17C	109.5
C5—C6—C7	119.7 (3)	H17A—C17—H17C	109.5
C5—C6—H6A	120.2	H17B—C17—H17C	109.5
C7—C6—H6A	120.2	O4—C18—C20	106.7 (3)
C2—C7—C6	121.0 (3)	O4—C18—C19	110.1 (3)
C2—C7—H7A	119.5	C20—C18—C19	113.7 (4)
C6—C7—H7A	119.5	O4—C18—H18A	108.7
N1—C8—C9	112.6 (2)	C20—C18—H18A	108.7
N1—C8—P1	112.04 (18)	C19—C18—H18A	108.7
C9—C8—P1	113.18 (19)	C18—C19—H19A	109.5
N1—C8—H8A	106.1	C18—C19—H19B	109.5
C9—C8—H8A	106.1	H19A—C19—H19B	109.5
P1—C8—H8A	106.1	C18—C19—H19C	109.5
C14—C9—C10	118.1 (3)	H19A—C19—H19C	109.5
C14—C9—C8	120.7 (3)	H19B—C19—H19C	109.5
C10—C9—C8	121.0 (2)	C18—C20—H20A	109.5
C11—C10—C9	120.5 (3)	C18—C20—H20B	109.5
C11—C10—H10A	119.7	H20A—C20—H20B	109.5
C9—C10—H10A	119.7	C18—C20—H20C	109.5
C12—C11—C10	120.5 (3)	H20A—C20—H20C	109.5
C12—C11—H11A	119.7	H20B—C20—H20C	109.5

C8—N1—C1—O1	−3.5 (4)	O2—P1—C8—N1	82.0 (2)
C8—N1—C1—C2	175.2 (2)	O3—P1—C8—N1	−40.9 (2)
O1—C1—C2—C3	6.2 (4)	O4—P1—C8—N1	−153.99 (19)
N1—C1—C2—C3	−172.5 (3)	O2—P1—C8—C9	−46.6 (2)
O1—C1—C2—C7	−174.3 (3)	O3—P1—C8—C9	−169.52 (19)
N1—C1—C2—C7	7.0 (4)	O4—P1—C8—C9	77.4 (2)
O2—P1—O3—C15	−173.2 (2)	N1—C8—C9—C14	116.7 (3)
O4—P1—O3—C15	61.0 (3)	P1—C8—C9—C14	−115.0 (3)
C8—P1—O3—C15	−45.8 (3)	N1—C8—C9—C10	−58.9 (4)
C7—C2—C3—C4	−2.5 (5)	P1—C8—C9—C10	69.4 (3)
C1—C2—C3—C4	177.0 (3)	C14—C9—C10—C11	−0.7 (5)
O2—P1—O4—C18	−19.8 (3)	C8—C9—C10—C11	174.9 (3)
O3—P1—O4—C18	102.8 (2)	C9—C10—C11—C12	1.0 (5)
C8—P1—O4—C18	−145.1 (2)	C10—C11—C12—C13	−0.4 (6)
C2—C3—C4—C5	1.4 (6)	C11—C12—C13—C14	−0.5 (6)
C3—C4—C5—C6	0.3 (6)	C10—C9—C14—C13	−0.2 (5)
C4—C5—C6—C7	−0.8 (5)	C8—C9—C14—C13	−175.8 (3)
C3—C2—C7—C6	2.0 (5)	C12—C13—C14—C9	0.8 (5)
C1—C2—C7—C6	−177.4 (3)	P1—O3—C15—C16	136.8 (3)
C5—C6—C7—C2	−0.4 (6)	P1—O3—C15—C17	−100.8 (3)
C1—N1—C8—C9	−101.9 (3)	P1—O4—C18—C20	156.8 (3)
C1—N1—C8—P1	129.2 (2)	P1—O4—C18—C19	−79.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.05	2.895 (3)	165

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₆NO₄P
M_r	375.39
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	10.839 (4), 10.925 (5), 11.057 (5)
α, β, γ (°)	61.364 (8), 83.362 (8), 60.470 (6)
V (Å³)	987.3 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.28 × 0.21 × 0.05

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.956, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	4991, 3411, 2509
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.174, 0.98
No. of reflections	3411
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.44

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.05	2.895 (3)	165.4

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 40806032) and the Scientific Research Foundation of the Third Institute of Oceanography, SOA (No. 2009005).

References

Babak, K. & Rahman, N. (2001). Synth. Commun. 31, 2245–2250. Web of Science CrossRef Google Scholar
Bruker (2001). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, R., Liu, L. & Zhang, Z. (1995). Heteroatom. Chem. 6, 503–506. CrossRef CAS Web of Science Google Scholar
Drescher, M., Hammerschmidt, F. & Kählig, H. (1995). Synthesis, 10, 1267–1272. CrossRef Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smaardijk, Ab. A., Noorda, S., van Bolhuis, F. & Wynberg, H. (1985). Tetrahedron Lett. 26, 493–496. CSD CrossRef CAS Web of Science Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stowasser, B., Budt, K.-H., Jian-Qi, L., Peyman, A. & Ruppert, D. (1992). Tetrahedron Lett. 33, 6625–6628. CrossRef CAS Web of Science Google Scholar