2-[3-(Trifluoro­meth­yl)phen­oxy]ethyl 1-oxo-2,6,7-trioxa-1λ5-phosphabicyclo­[2.2.2]octane-4-carboxyl­ate

Wang, W.; Wang, W.-D.; Wang, S.-B.; Shen, Y.-L.; He, H.-W.

doi:10.1107/S1600536808003735

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o582

doi:10.1107/S1600536808003735

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2-[3-(Trifluoromethyl)phenoxy]ethyl 1-oxo-2,6,7-trioxa-1λ⁵-phosphabicyclo[2.2.2]octane-4-carboxylate

Wei Wang,^a Wei-Dong Wang,^a Shao-Bin Wang,^a Yun-Li Shen ^a and Hong-Wu He ^a ^*

^aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: he1208@mail.ccnu.edu.cn

(Received 22 November 2007; accepted 4 February 2008; online 13 February 2008)

In the crystal structure of the title compound, C₁₄H₁₄F₃O₇P, the central chain, which connects the phosphate bicyclic system and the benzene ring, is made up of an approximately planar C—C(O)—O—C(H₂) fragment and a C(H₂)—O—C(Ph) link; the mean planes make a dihedral angle of 75.9 (2)°. The F atoms are disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

Related literature

For industrial and biological applications of heterocyclic compounds involving bicyclic phosphate, see: Ratz (1966 ); Li et al., (2002 ). Many related derivatives have been prepared by Verkade & Reynolds (1960 ) and Sheng & He (2006 ). For the synthesis of the starting material, see: Chen & Jin (2000 ). For related literature, see: Nimrod et al. (1968 ).

Experimental

Crystal data

C₁₄H₁₄F₃O₇P
M_r = 382.22
Monoclinic, P 2₁ /n
a = 5.7824 (3) Å
b = 27.5060 (16) Å
c = 10.2878 (6) Å
β = 96.738 (1)°
V = 1624.98 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 295 (2) K
0.30 × 0.20 × 0.06 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: none
18233 measured reflections
3547 independent reflections
2332 reflections with I > 2σ(I)
R_int = 0.091

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.137
S = 0.98
3547 reflections
254 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003735/ya2064sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003735/ya2064Isup2.hkl

checkCIF report

Comment top

Heterocyclic derivatives containing bicyclic phosphate system are important compounds with versatile industrial and biological applications (Ratz, 1966; Li et al., 2002). In continuation of our work on new biologically active heterocyclic derivatives, we report here the crystal structure of the title compound,(I) (Fig.1).Bond lengths and angles of the phosphorus-containing bicyclic cage of (I) are close to those observed previously in similar compounds (Nimrod et al., 1968; Sheng & He, 2006). The central chain of the molecule, which connects phosphate bicyclic system and benzene ring, is made up of approximately planar C4—C5—O6—C6 fragment and C7—O7—C8 link; their mean planes form dihedral angle of 75.9 (2)°.

Related literature top

For industrial and biological applications of heterocyclic compounds involving bicyclic phosphate, see: Ratz (1966); Li et al., (2002). Many related derivatives have been prepared by Verkade & Reynolds (1960) and Sheng & He (2006). For the synthesis of the starting material, see: Chen & Jin (2000).

For related literature, see: Nimrod et al. (1968).

Experimental top

The solution of anhydrous 1-oxo-2,6,7-trioxa-1λ⁵-phospha-bicyclo[2.2.2] octane-4-carbonyl chloride (Chen & Jin, 2000) (1.14 g, 0.0055 mol) in 5 ml of acetonitrile was added dropwise under stirring to the solution of 2-(3-trifluoromethylphenoxy)ethanol (1.03 g, 0.005 mol) and triethylamine (0.61 g, 0.006 mol) in 25 ml of acetonitrile. The stirring was continued for about 3 h. Then, the solvent was removed under reduced pressure and the residue was washed with water (20 ml). The raw product was recrystallized from acetonitrile, yielding the title compound as a white solid with 81% yield. Colourless crystals of (I) suitable for X-ray structure analysis were grown from the mixture of dichloromethane and n-hexane (v/v, 1:8).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme; the minor component of the CF₃ group disorder is omitted. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. Packing diagram for (I).
	Fig. 3. The formation of the title compound, (I).

2-[3-(Trifluoromethyl)phenoxy]ethyl 1-oxo-2,6,7-trioxa-1λ⁵-phosphabicyclo[2.2.2]octane-4-carboxylate top

Crystal data top

C₁₄H₁₄F₃O₇P	F(000) = 784
M_r = 382.22	D_x = 1.562 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4355 reflections
a = 5.7824 (3) Å	θ = 2.4–19.3°
b = 27.5060 (16) Å	µ = 0.24 mm⁻¹
c = 10.2878 (6) Å	T = 295 K
β = 96.738 (1)°	Plate, colourless
V = 1624.98 (16) Å³	0.30 × 0.20 × 0.06 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2332 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.091
Graphite monochromator	θ_max = 27.0°, θ_min = 1.5°
ϕ and ω scans	h = −7→7
18233 measured reflections	k = −35→35
3547 independent reflections	l = −13→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0771P)²] where P = (F_o² + 2F_c²)/3
3547 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.27 e Å⁻³
30 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₁₄F₃O₇P	V = 1624.98 (16) Å³
M_r = 382.22	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.7824 (3) Å	µ = 0.24 mm⁻¹
b = 27.5060 (16) Å	T = 295 K
c = 10.2878 (6) Å	0.30 × 0.20 × 0.06 mm
β = 96.738 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2332 reflections with I > 2σ(I)
18233 measured reflections	R_int = 0.091
3547 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	30 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 0.98	Δρ_max = 0.27 e Å⁻³
3547 reflections	Δρ_min = −0.22 e Å⁻³
254 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	Occ. (<1)
C1	0.3969 (4)	0.14250 (8)	0.3106 (2)	0.0518 (6)
H1A	0.5300	0.1356	0.3744	0.062*
H1B	0.3031	0.1133	0.2985	0.062*
C2	0.4076 (4)	0.22884 (9)	0.3762 (2)	0.0502 (6)
H2A	0.3254	0.2552	0.4134	0.060*
H2B	0.5473	0.2218	0.4350	0.060*
C3	0.0422 (4)	0.19358 (11)	0.2599 (2)	0.0579 (7)
H3A	−0.0585	0.1653	0.2523	0.069*
H3B	−0.0459	0.2207	0.2886	0.069*
C4	0.2525 (3)	0.18376 (8)	0.3603 (2)	0.0405 (5)
C5	0.1682 (4)	0.16870 (8)	0.4885 (2)	0.0479 (6)
C6	0.2903 (5)	0.15256 (10)	0.7125 (2)	0.0630 (7)
H6A	0.1908	0.1241	0.7030	0.076*
H6B	0.2108	0.1778	0.7559	0.076*
C7	0.5158 (5)	0.14044 (9)	0.7905 (2)	0.0602 (7)
H7A	0.6266	0.1666	0.7853	0.072*
H7B	0.4938	0.1356	0.8817	0.072*
C8	0.8002 (4)	0.07776 (9)	0.7983 (2)	0.0497 (6)
C9	0.8907 (5)	0.03932 (9)	0.7345 (2)	0.0567 (7)
H9	0.8138	0.0281	0.6557	0.068*
C10	1.0948 (5)	0.01744 (10)	0.7873 (3)	0.0665 (8)
C11	1.2075 (6)	0.03407 (13)	0.9055 (3)	0.0844 (9)
H11	1.3452	0.0195	0.9418	0.101*
C12	1.1166 (6)	0.07149 (13)	0.9678 (3)	0.0832 (9)
H12	1.1933	0.0824	1.0469	0.100*
C13	0.9127 (5)	0.09386 (10)	0.9166 (2)	0.0657 (7)
H13	0.8516	0.1194	0.9610	0.079*
C14	1.1925 (6)	−0.02293 (13)	0.7178 (4)	0.0947 (11)
F1	1.0315 (9)	−0.0476 (3)	0.6324 (13)	0.136 (3)	0.591 (16)
F2	1.3280 (17)	−0.0092 (4)	0.6315 (8)	0.136 (4)	0.591 (16)
F3	1.295 (3)	−0.0570 (4)	0.7881 (7)	0.202 (7)	0.591 (16)
F1'	1.0849 (18)	−0.0629 (3)	0.7297 (14)	0.115 (5)	0.409 (16)
F2'	1.4149 (10)	−0.0324 (4)	0.7722 (12)	0.113 (4)	0.409 (16)
F3'	1.218 (3)	−0.0137 (5)	0.5991 (8)	0.135 (6)	0.409 (16)
O1	0.4623 (3)	0.22048 (7)	0.00883 (16)	0.0676 (5)
O2	0.4701 (3)	0.24307 (6)	0.24834 (15)	0.0583 (5)
O3	0.4763 (3)	0.15669 (6)	0.18650 (16)	0.0570 (5)
O4	0.1178 (3)	0.20463 (7)	0.13298 (16)	0.0661 (5)
O5	−0.0280 (3)	0.15716 (8)	0.49924 (19)	0.0766 (6)
O6	0.3411 (3)	0.16937 (6)	0.58442 (16)	0.0580 (5)
O7	0.5992 (3)	0.09700 (6)	0.73729 (15)	0.0592 (5)
P1	0.38795 (10)	0.20768 (2)	0.13331 (6)	0.0473 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0521 (14)	0.0443 (13)	0.0594 (15)	0.0020 (10)	0.0080 (11)	−0.0002 (11)
C2	0.0553 (15)	0.0499 (13)	0.0472 (14)	−0.0098 (11)	0.0134 (11)	−0.0049 (11)
C3	0.0347 (13)	0.0757 (17)	0.0628 (16)	0.0004 (11)	0.0039 (11)	0.0092 (13)
C4	0.0319 (11)	0.0415 (12)	0.0478 (13)	−0.0008 (9)	0.0041 (9)	−0.0008 (9)
C5	0.0428 (13)	0.0444 (13)	0.0577 (15)	−0.0006 (10)	0.0116 (12)	0.0022 (11)
C6	0.0696 (18)	0.0645 (16)	0.0583 (16)	0.0197 (13)	0.0215 (13)	0.0145 (13)
C7	0.0821 (19)	0.0515 (14)	0.0485 (14)	0.0154 (13)	0.0141 (13)	−0.0017 (11)
C8	0.0545 (14)	0.0476 (13)	0.0467 (13)	0.0021 (11)	0.0042 (11)	0.0045 (11)
C9	0.0610 (16)	0.0507 (14)	0.0583 (16)	−0.0001 (12)	0.0065 (13)	−0.0031 (12)
C10	0.0608 (17)	0.0529 (15)	0.086 (2)	0.0086 (13)	0.0088 (16)	0.0105 (14)
C11	0.070 (2)	0.086 (2)	0.092 (2)	0.0152 (17)	−0.0144 (18)	0.018 (2)
C12	0.085 (2)	0.089 (2)	0.0686 (19)	−0.0008 (18)	−0.0211 (17)	0.0045 (17)
C13	0.083 (2)	0.0616 (16)	0.0499 (15)	0.0021 (14)	−0.0007 (14)	−0.0002 (12)
C14	0.085 (3)	0.079 (3)	0.120 (3)	0.024 (2)	0.012 (3)	−0.001 (2)
F1	0.126 (4)	0.084 (4)	0.202 (9)	0.010 (3)	0.037 (5)	−0.061 (5)
F2	0.108 (5)	0.159 (6)	0.151 (8)	−0.032 (5)	0.055 (5)	−0.069 (6)
F3	0.268 (16)	0.152 (9)	0.190 (7)	0.147 (11)	0.042 (9)	0.040 (6)
F1'	0.123 (6)	0.066 (5)	0.163 (11)	−0.031 (4)	0.044 (7)	−0.051 (6)
F2'	0.062 (4)	0.092 (5)	0.178 (10)	0.033 (3)	−0.018 (4)	−0.038 (5)
F3'	0.165 (12)	0.141 (11)	0.099 (5)	0.060 (10)	0.018 (7)	−0.018 (6)
O1	0.0735 (13)	0.0802 (13)	0.0510 (11)	−0.0054 (10)	0.0153 (9)	0.0008 (9)
O2	0.0748 (12)	0.0507 (9)	0.0518 (10)	−0.0220 (8)	0.0168 (8)	−0.0027 (8)
O3	0.0627 (11)	0.0535 (10)	0.0572 (11)	0.0088 (8)	0.0178 (8)	−0.0041 (8)
O4	0.0411 (10)	0.1008 (14)	0.0544 (11)	0.0014 (9)	−0.0035 (8)	0.0136 (9)
O5	0.0527 (11)	0.0998 (15)	0.0798 (14)	−0.0187 (10)	0.0189 (10)	0.0094 (11)
O6	0.0479 (10)	0.0716 (11)	0.0551 (10)	0.0023 (8)	0.0082 (8)	0.0188 (9)
O7	0.0657 (11)	0.0579 (10)	0.0524 (10)	0.0154 (8)	−0.0006 (8)	−0.0095 (8)
P1	0.0443 (4)	0.0516 (4)	0.0460 (4)	−0.0027 (3)	0.0054 (3)	−0.0017 (3)

Geometric parameters (Å, º) top

C1—O3	1.460 (3)	C8—O7	1.361 (3)
C1—C4	1.532 (3)	C8—C9	1.380 (3)
C1—H1A	0.9700	C8—C13	1.384 (3)
C1—H1B	0.9700	C9—C10	1.378 (4)
C2—O2	1.458 (2)	C9—H9	0.9300
C2—C4	1.528 (3)	C10—C11	1.388 (4)
C2—H2A	0.9700	C10—C14	1.469 (5)
C2—H2B	0.9700	C11—C12	1.351 (5)
C3—O4	1.457 (3)	C11—H11	0.9300
C3—C4	1.525 (3)	C12—C13	1.378 (4)
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700	C13—H13	0.9300
C4—C5	1.516 (3)	C14—F3'	1.274 (7)
C5—O5	1.196 (3)	C14—F1'	1.277 (6)
C5—O6	1.320 (3)	C14—F3	1.284 (5)
C6—O6	1.459 (3)	C14—F2	1.307 (6)
C6—C7	1.487 (3)	C14—F2'	1.366 (6)
C6—H6A	0.9700	C14—F1	1.382 (6)
C6—H6B	0.9700	O1—P1	1.4416 (18)
C7—O7	1.422 (3)	O2—P1	1.5625 (16)
C7—H7A	0.9700	O3—P1	1.5689 (17)
C7—H7B	0.9700	O4—P1	1.5642 (18)

O3—C1—C4	109.50 (18)	C9—C10—C11	119.6 (3)
O3—C1—H1A	109.8	C9—C10—C14	119.9 (3)
C4—C1—H1A	109.8	C11—C10—C14	120.5 (3)
O3—C1—H1B	109.8	C12—C11—C10	119.9 (3)
C4—C1—H1B	109.8	C12—C11—H11	120.1
H1A—C1—H1B	108.2	C10—C11—H11	120.1
O2—C2—C4	109.03 (16)	C11—C12—C13	121.5 (3)
O2—C2—H2A	109.9	C11—C12—H12	119.3
C4—C2—H2A	109.9	C13—C12—H12	119.3
O2—C2—H2B	109.9	C12—C13—C8	119.1 (3)
C4—C2—H2B	109.9	C12—C13—H13	120.5
H2A—C2—H2B	108.3	C8—C13—H13	120.5
O4—C3—C4	110.18 (18)	F3'—C14—F1'	112.2 (6)
O4—C3—H3A	109.6	F3'—C14—F3	125.9 (8)
C4—C3—H3A	109.6	F1'—C14—F3	61.0 (5)
O4—C3—H3B	109.6	F3'—C14—F2	31.0 (6)
C4—C3—H3B	109.6	F1'—C14—F2	130.6 (7)
H3A—C3—H3B	108.1	F3—C14—F2	108.7 (5)
C5—C4—C3	108.98 (18)	F3'—C14—F2'	102.7 (6)
C5—C4—C2	111.94 (18)	F1'—C14—F2'	104.0 (5)
C3—C4—C2	109.88 (19)	F3—C14—F2'	44.0 (5)
C5—C4—C1	109.37 (18)	F2—C14—F2'	73.9 (5)
C3—C4—C1	109.12 (19)	F3'—C14—F1	68.6 (6)
C2—C4—C1	107.51 (18)	F1'—C14—F1	48.5 (4)
O5—C5—O6	125.3 (2)	F3—C14—F1	103.3 (5)
O5—C5—C4	124.0 (2)	F2—C14—F1	97.1 (5)
O6—C5—C4	110.72 (18)	F2'—C14—F1	134.3 (5)
O6—C6—C7	107.6 (2)	F3'—C14—C10	114.3 (6)
O6—C6—H6A	110.2	F1'—C14—C10	112.7 (4)
C7—C6—H6A	110.2	F3—C14—C10	117.1 (5)
O6—C6—H6B	110.2	F2—C14—C10	114.0 (5)
C7—C6—H6B	110.2	F2'—C14—C10	110.0 (5)
H6A—C6—H6B	108.5	F1—C14—C10	114.4 (3)
O7—C7—C6	107.2 (2)	C2—O2—P1	115.51 (13)
O7—C7—H7A	110.3	C1—O3—P1	114.91 (13)
C6—C7—H7A	110.3	C3—O4—P1	114.44 (13)
O7—C7—H7B	110.3	C5—O6—C6	117.12 (18)
C6—C7—H7B	110.3	C8—O7—C7	117.31 (18)
H7A—C7—H7B	108.5	O1—P1—O2	115.14 (10)
O7—C8—C9	115.4 (2)	O1—P1—O4	114.40 (10)
O7—C8—C13	124.7 (2)	O2—P1—O4	104.46 (10)
C9—C8—C13	119.9 (2)	O1—P1—O3	114.17 (10)
C10—C9—C8	120.1 (2)	O2—P1—O3	103.61 (9)
C10—C9—H9	119.9	O4—P1—O3	103.71 (10)
C8—C9—H9	119.9

O4—C3—C4—C5	−175.80 (19)	C9—C10—C14—F1'	−76.8 (9)
O4—C3—C4—C2	61.2 (3)	C11—C10—C14—F1'	103.7 (9)
O4—C3—C4—C1	−56.4 (3)	C9—C10—C14—F3	−144.7 (10)
O2—C2—C4—C5	−176.43 (17)	C11—C10—C14—F3	35.8 (11)
O2—C2—C4—C3	−55.2 (2)	C9—C10—C14—F2	86.9 (7)
O2—C2—C4—C1	63.4 (2)	C11—C10—C14—F2	−92.6 (7)
O3—C1—C4—C5	179.40 (17)	C9—C10—C14—F2'	167.6 (7)
O3—C1—C4—C3	60.3 (2)	C11—C10—C14—F2'	−11.9 (8)
O3—C1—C4—C2	−58.9 (2)	C9—C10—C14—F1	−23.6 (8)
C3—C4—C5—O5	13.7 (3)	C11—C10—C14—F1	156.9 (7)
C2—C4—C5—O5	135.5 (2)	C4—C2—O2—P1	−5.5 (2)
C1—C4—C5—O5	−105.5 (3)	C4—C1—O3—P1	−2.6 (2)
C3—C4—C5—O6	−167.4 (2)	C4—C3—O4—P1	−4.5 (3)
C2—C4—C5—O6	−45.6 (3)	O5—C5—O6—C6	2.9 (4)
C1—C4—C5—O6	73.4 (2)	C4—C5—O6—C6	−175.99 (19)
O6—C6—C7—O7	−71.8 (3)	C7—C6—O6—C5	161.0 (2)
O7—C8—C9—C10	179.5 (2)	C9—C8—O7—C7	−172.2 (2)
C13—C8—C9—C10	−1.0 (4)	C13—C8—O7—C7	8.4 (4)
C8—C9—C10—C11	0.5 (4)	C6—C7—O7—C8	−176.9 (2)
C8—C9—C10—C14	−179.0 (3)	C2—O2—P1—O1	−176.46 (15)
C9—C10—C11—C12	0.0 (5)	C2—O2—P1—O4	57.23 (18)
C14—C10—C11—C12	179.5 (3)	C2—O2—P1—O3	−51.09 (18)
C10—C11—C12—C13	0.0 (5)	C3—O4—P1—O1	−177.70 (18)
C11—C12—C13—C8	−0.5 (5)	C3—O4—P1—O2	−50.93 (19)
O7—C8—C13—C12	−179.5 (3)	C3—O4—P1—O3	57.31 (19)
C9—C8—C13—C12	1.0 (4)	C1—O3—P1—O1	−178.26 (15)
C9—C10—C14—F3'	52.8 (10)	C1—O3—P1—O2	55.75 (17)
C11—C10—C14—F3'	−126.7 (10)	C1—O3—P1—O4	−53.13 (17)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄F₃O₇P
M_r	382.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	5.7824 (3), 27.5060 (16), 10.2878 (6)
β (°)	96.738 (1)
V (Å³)	1624.98 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.20 × 0.06

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18233, 3547, 2332
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.137, 0.98
No. of reflections	3547
No. of parameters	254
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Acknowledgements

We gratefully acknowledge financial support of this work by the National Basic Research Program of China (2003CB114400) and the National Natural Science Foundation of China (No. 20772042).

References

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