(Dimeth­oxy­phosphor­yl)(furan-2-yl)methyl 2-(2,4-dichloro­phen­oxy)acetate

Tan, X.; Peng, H.; He, H.

doi:10.1107/S1600536810042820

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2962

https://doi.org/10.1107/S1600536810042820

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(Dimethoxyphosphoryl)(furan-2-yl)methyl 2-(2,4-dichlorophenoxy)acetate

Xiaosong Tan,^a ^* Hao Peng ^a and Hongwu He ^a

^aKey Laboratory of Pesticide and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: txs3542@mail.ccnu.edu.cn

(Received 15 October 2010; accepted 21 October 2010; online 30 October 2010)

In the title compound, C₁₅H₁₅Cl₂O₇P, the benzene and furan rings form a dihedral angle of 73.54 (1)°. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into layers parallel to (100).

Related literature

For the synthesis and biological activity of 1-(substituted phenoxyacetoxy)alkylphosphonate derivatives, see: He et al. (2001 , 2005 ); Chen et al. (2006 ). The synthesis and biological activity of the title compound have been discussed by Peng et al. (2007 ).

Experimental

Crystal data

C₁₅H₁₅Cl₂O₇P
M_r = 409.14
Monoclinic, P 2₁ /c
a = 8.5380 (7) Å
b = 17.3111 (14) Å
c = 12.4003 (10) Å
β = 98.475 (1)°
V = 1812.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 292 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
12335 measured reflections
4135 independent reflections
3158 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.133
S = 1.05
4135 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O5ⁱ	0.93	2.50	3.322 (3)	148
C9—H9⋯O2ⁱⁱ	0.98	2.35	3.270 (2)	157
C14—H14B⋯O5ⁱ	0.96	2.44	3.379 (3)	165
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810042820/cv2778sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042820/cv2778Isup2.hkl

checkCIF report

Comment top

Phosphonate derivatives are particularly important in connection with their remarkable biological activities. They have been widely used as enzyme inhibitors, antibacterial agents, anti-HIV agents, and also used as pesticides. As a continuation of our search for novel herbicides, series of 1-(substituted phenoxyacetoxy)alkylphosphonate derivatives have been designed and synthesized. Some of them have shown good herbicidal activities acting as inhibitors of PDHc (He et al., 2001, 2005; Chen et al., 2006; Peng et al., 2007). The title compound (I) can be used as herbicide to control broadleaf weeds and sedge weeds effectively and showed good selectivity between monocotyledonous crops and dicotyledonous weeds. Here, we report the crystal structure of (I).

The title compound (Fig. 1), has formed a racemate crystal with monoclinic (P2₁/c) symmetry. The benzene and furan rings in the molecule are nonplanar, and the dihedral angle between the two rings is 73.54 (1)°.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to the (100) plane. Weak C—H···π interaction (C15···Cg1 = 3.690 (3) Å, C15—H15···Cg1=137°, symmetry code: x, y, z, Cg1 is the centroid defined by atoms O4/C10—C13) was also observed in the crystal structure.

Related literature top

For the synthesis and biological activity of 1-(substituted phenoxyacetoxy)alkylphosphonate derivatives, see: He et al. (2001, 2005); Chen et al. (2006). The synthesis and biological activity of the title compound have been discussed by Peng et al. (2007).

Experimental top

A solution of 2,4-dichorophenoxyacetyl chloride (11 mmol) in trichloromethane (15 ml) was added to stirred mixture of 1-hydroxy (furan-2-yl)methylphosphonate (10 mmol) and triethyl amine (11 mmol) in trichloromethane (15 ml) at 273 K. The resultant mixture was stirred at ambient temperature for 3 h, then washed with dilute hydrochloric acid solution, saturated sodium hydrogen carbonate and brine separately, dried and evaporated. The residue was chromatographed on silica with acetone and petroleum ether as eluent to give the title compound as a white solid.

Structure description top

For the synthesis and biological activity of 1-(substituted phenoxyacetoxy)alkylphosphonate derivatives, see: He et al. (2001, 2005); Chen et al. (2006). The synthesis and biological activity of the title compound have been discussed by Peng et al. (2007).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme for the non-H atoms and 50% probability displacement ellipsoids.
	Fig. 2. Part of the crystal packing, showing the C—H···O hydrogen bonds as dashed lines.

(Dimethoxyphosphoryl)(furan-2-yl)methyl 2-(2,4-dichlorophenoxy)acetate top

Crystal data top

C₁₅H₁₅Cl₂O₇P	F(000) = 840
M_r = 409.14	D_x = 1.499 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4066 reflections
a = 8.5380 (7) Å	θ = 2.4–28.2°
b = 17.3111 (14) Å	µ = 0.48 mm⁻¹
c = 12.4003 (10) Å	T = 292 K
β = 98.475 (1)°	Block, colourless
V = 1812.8 (3) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3158 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
phi and ω scans	h = −11→11
12335 measured reflections	k = −22→19
4135 independent reflections	l = −15→15

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0672P)² + 0.2806P] where P = (F_o² + 2F_c²)/3
4135 reflections	(Δ/σ)_max = 0.001
228 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₅H₁₅Cl₂O₇P	V = 1812.8 (3) Å³
M_r = 409.14	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5380 (7) Å	µ = 0.48 mm⁻¹
b = 17.3111 (14) Å	T = 292 K
c = 12.4003 (10) Å	0.30 × 0.20 × 0.20 mm
β = 98.475 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3158 reflections with I > 2σ(I)
12335 measured reflections	R_int = 0.048
4135 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.05	Δρ_max = 0.36 e Å⁻³
4135 reflections	Δρ_min = −0.31 e Å⁻³
228 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
C1	0.6128 (3)	0.35463 (14)	0.10119 (19)	0.0489 (5)
C2	0.4929 (3)	0.40648 (14)	0.10635 (19)	0.0545 (6)
H2	0.4350	0.4262	0.0429	0.065*
C3	0.4592 (3)	0.42900 (14)	0.20734 (19)	0.0474 (5)
C4	0.5448 (2)	0.40033 (12)	0.30291 (17)	0.0377 (4)
C5	0.6644 (2)	0.34767 (12)	0.29467 (18)	0.0411 (5)
H5	0.7220	0.3274	0.3578	0.049*
C6	0.7000 (3)	0.32463 (13)	0.1940 (2)	0.0459 (5)
H6	0.7812	0.2896	0.1892	0.055*
C7	0.5786 (2)	0.39588 (13)	0.49683 (17)	0.0412 (5)
H7A	0.5747	0.3400	0.4922	0.049*
H7B	0.5227	0.4116	0.5559	0.049*
C8	0.7491 (2)	0.42157 (12)	0.52171 (16)	0.0361 (4)
C9	0.9975 (2)	0.39109 (12)	0.62871 (16)	0.0361 (4)
H9	1.0269	0.4344	0.5849	0.043*
C10	1.0363 (2)	0.41187 (12)	0.74493 (17)	0.0390 (5)
C11	1.1050 (3)	0.47563 (13)	0.78872 (19)	0.0449 (5)
H11	1.1352	0.5186	0.7517	0.054*
C12	1.1229 (3)	0.46505 (18)	0.9034 (2)	0.0631 (7)
H12	1.1684	0.4998	0.9560	0.076*
C13	1.0633 (3)	0.39691 (18)	0.9214 (2)	0.0642 (7)
H13	1.0593	0.3757	0.9898	0.077*
C14	1.1220 (4)	0.35140 (18)	0.3883 (2)	0.0681 (8)
H14A	1.0862	0.4032	0.3976	0.102*
H14B	1.0867	0.3348	0.3149	0.102*
H14C	1.2355	0.3499	0.4026	0.102*
C15	1.3707 (3)	0.3126 (2)	0.7176 (2)	0.0762 (9)
H15A	1.3491	0.3517	0.7684	0.114*
H15B	1.4810	0.3138	0.7104	0.114*
H15C	1.3442	0.2628	0.7438	0.114*
Cl1	0.65651 (11)	0.32723 (5)	−0.02623 (6)	0.0777 (3)
Cl2	0.30927 (9)	0.49516 (5)	0.21544 (6)	0.0819 (3)
O1	0.50190 (16)	0.42765 (9)	0.39781 (12)	0.0444 (4)
O2	0.80530 (19)	0.47377 (9)	0.47743 (14)	0.0548 (4)
O3	0.82710 (15)	0.37669 (8)	0.59892 (11)	0.0394 (3)
O4	1.0077 (2)	0.36170 (10)	0.82338 (14)	0.0610 (5)
O5	1.0513 (2)	0.23366 (9)	0.64065 (14)	0.0552 (4)
O6	1.0582 (2)	0.30095 (10)	0.46306 (13)	0.0546 (4)
O7	1.27695 (17)	0.32711 (10)	0.61288 (14)	0.0510 (4)
P1	1.09650 (6)	0.30439 (3)	0.58986 (5)	0.04063 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0557 (13)	0.0517 (14)	0.0399 (12)	−0.0049 (11)	0.0090 (10)	−0.0065 (10)
C2	0.0591 (14)	0.0644 (16)	0.0368 (13)	0.0079 (12)	−0.0036 (11)	0.0024 (11)
C3	0.0411 (11)	0.0545 (13)	0.0442 (13)	0.0110 (10)	−0.0014 (10)	0.0008 (11)
C4	0.0301 (9)	0.0439 (11)	0.0377 (11)	−0.0011 (8)	0.0003 (8)	−0.0009 (9)
C5	0.0352 (10)	0.0446 (12)	0.0415 (12)	0.0010 (9)	−0.0015 (9)	0.0027 (9)
C6	0.0425 (11)	0.0432 (12)	0.0522 (14)	0.0026 (9)	0.0082 (10)	−0.0050 (10)
C7	0.0357 (10)	0.0517 (13)	0.0356 (11)	−0.0018 (9)	0.0031 (8)	0.0030 (9)
C8	0.0373 (10)	0.0402 (11)	0.0301 (10)	−0.0008 (8)	0.0023 (8)	−0.0016 (8)
C9	0.0308 (9)	0.0402 (11)	0.0362 (11)	−0.0047 (8)	0.0018 (8)	0.0062 (9)
C10	0.0356 (10)	0.0443 (12)	0.0369 (11)	0.0040 (9)	0.0046 (9)	0.0037 (9)
C11	0.0509 (13)	0.0404 (12)	0.0436 (13)	−0.0089 (10)	0.0070 (10)	−0.0034 (10)
C12	0.0587 (15)	0.0773 (19)	0.0502 (15)	0.0000 (14)	−0.0022 (12)	−0.0206 (14)
C13	0.0732 (17)	0.084 (2)	0.0352 (13)	0.0139 (16)	0.0064 (12)	0.0061 (13)
C14	0.0799 (19)	0.088 (2)	0.0378 (14)	−0.0214 (16)	0.0133 (13)	0.0000 (13)
C15	0.0442 (14)	0.116 (3)	0.0642 (19)	0.0139 (15)	−0.0057 (13)	0.0160 (17)
Cl1	0.1028 (6)	0.0855 (5)	0.0477 (4)	0.0091 (4)	0.0213 (4)	−0.0122 (3)
Cl2	0.0755 (5)	0.1100 (6)	0.0563 (4)	0.0552 (4)	−0.0029 (3)	0.0040 (4)
O1	0.0355 (7)	0.0607 (10)	0.0353 (8)	0.0096 (7)	−0.0004 (6)	−0.0011 (7)
O2	0.0500 (9)	0.0558 (10)	0.0541 (10)	−0.0142 (8)	−0.0072 (7)	0.0202 (8)
O3	0.0322 (7)	0.0458 (8)	0.0389 (8)	−0.0049 (6)	0.0004 (6)	0.0105 (6)
O4	0.0774 (12)	0.0568 (11)	0.0505 (10)	−0.0025 (9)	0.0147 (9)	0.0053 (8)
O5	0.0657 (10)	0.0453 (9)	0.0558 (10)	−0.0021 (8)	0.0123 (8)	0.0066 (8)
O6	0.0633 (10)	0.0619 (10)	0.0387 (9)	−0.0138 (8)	0.0074 (8)	−0.0046 (7)
O7	0.0370 (8)	0.0686 (11)	0.0468 (9)	0.0026 (7)	0.0043 (7)	0.0063 (8)
P1	0.0402 (3)	0.0448 (3)	0.0369 (3)	−0.0021 (2)	0.0060 (2)	0.0002 (2)

Geometric parameters (Å, º) top

C1—C2	1.370 (3)	C9—H9	0.9800
C1—C6	1.377 (3)	C10—C11	1.328 (3)
C1—Cl1	1.742 (2)	C10—O4	1.353 (2)
C2—C3	1.382 (3)	C11—C12	1.419 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.389 (3)	C12—C13	1.317 (4)
C3—Cl2	1.732 (2)	C12—H12	0.9300
C4—O1	1.367 (2)	C13—O4	1.380 (3)
C4—C5	1.384 (3)	C13—H13	0.9300
C5—C6	1.386 (3)	C14—O6	1.438 (3)
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—O1	1.415 (2)	C14—H14C	0.9600
C7—C8	1.509 (3)	C15—O7	1.444 (3)
C7—H7A	0.9700	C15—H15A	0.9600
C7—H7B	0.9700	C15—H15B	0.9600
C8—O2	1.194 (2)	C15—H15C	0.9600
C8—O3	1.333 (2)	O5—P1	1.4548 (16)
C9—O3	1.468 (2)	O6—P1	1.5591 (17)
C9—C10	1.475 (3)	O7—P1	1.5749 (16)
C9—P1	1.822 (2)

C2—C1—C6	121.6 (2)	C11—C10—C9	128.6 (2)
C2—C1—Cl1	118.84 (19)	O4—C10—C9	120.50 (19)
C6—C1—Cl1	119.56 (19)	C10—C11—C12	106.2 (2)
C1—C2—C3	118.9 (2)	C10—C11—H11	126.9
C1—C2—H2	120.5	C12—C11—H11	126.9
C3—C2—H2	120.5	C13—C12—C11	107.3 (2)
C2—C3—C4	121.3 (2)	C13—C12—H12	126.3
C2—C3—Cl2	119.57 (18)	C11—C12—H12	126.3
C4—C3—Cl2	119.15 (18)	C12—C13—O4	109.7 (2)
O1—C4—C5	125.83 (19)	C12—C13—H13	125.1
O1—C4—C3	115.91 (19)	O4—C13—H13	125.1
C5—C4—C3	118.3 (2)	O6—C14—H14A	109.5
C4—C5—C6	121.2 (2)	O6—C14—H14B	109.5
C4—C5—H5	119.4	H14A—C14—H14B	109.5
C6—C5—H5	119.4	O6—C14—H14C	109.5
C1—C6—C5	118.7 (2)	H14A—C14—H14C	109.5
C1—C6—H6	120.6	H14B—C14—H14C	109.5
C5—C6—H6	120.6	O7—C15—H15A	109.5
O1—C7—C8	111.83 (16)	O7—C15—H15B	109.5
O1—C7—H7A	109.2	H15A—C15—H15B	109.5
C8—C7—H7A	109.2	O7—C15—H15C	109.5
O1—C7—H7B	109.2	H15A—C15—H15C	109.5
C8—C7—H7B	109.2	H15B—C15—H15C	109.5
H7A—C7—H7B	107.9	C4—O1—C7	117.64 (16)
O2—C8—O3	125.38 (18)	C8—O3—C9	116.97 (15)
O2—C8—C7	124.74 (19)	C10—O4—C13	105.9 (2)
O3—C8—C7	109.87 (17)	C14—O6—P1	125.73 (16)
O3—C9—C10	111.03 (15)	C15—O7—P1	121.16 (16)
O3—C9—P1	105.95 (13)	O5—P1—O6	112.02 (9)
C10—C9—P1	114.39 (14)	O5—P1—O7	116.52 (10)
O3—C9—H9	108.4	O6—P1—O7	104.26 (9)
C10—C9—H9	108.4	O5—P1—C9	114.57 (9)
P1—C9—H9	108.4	O6—P1—C9	105.17 (9)
C11—C10—O4	110.8 (2)	O7—P1—C9	103.06 (9)

C6—C1—C2—C3	0.0 (4)	C5—C4—O1—C7	−4.5 (3)
Cl1—C1—C2—C3	−179.22 (19)	C3—C4—O1—C7	175.69 (18)
C1—C2—C3—C4	0.2 (4)	C8—C7—O1—C4	71.0 (2)
C1—C2—C3—Cl2	179.42 (19)	O2—C8—O3—C9	−2.4 (3)
C2—C3—C4—O1	179.2 (2)	C7—C8—O3—C9	176.68 (16)
Cl2—C3—C4—O1	0.0 (3)	C10—C9—O3—C8	119.82 (19)
C2—C3—C4—C5	−0.6 (3)	P1—C9—O3—C8	−115.43 (16)
Cl2—C3—C4—C5	−179.82 (16)	C11—C10—O4—C13	−0.4 (3)
O1—C4—C5—C6	−178.97 (19)	C9—C10—O4—C13	177.36 (19)
C3—C4—C5—C6	0.8 (3)	C12—C13—O4—C10	0.0 (3)
C2—C1—C6—C5	0.2 (4)	C14—O6—P1—O5	−163.4 (2)
Cl1—C1—C6—C5	179.39 (16)	C14—O6—P1—O7	−36.6 (2)
C4—C5—C6—C1	−0.6 (3)	C14—O6—P1—C9	71.5 (2)
O1—C7—C8—O2	14.4 (3)	C15—O7—P1—O5	−36.0 (2)
O1—C7—C8—O3	−164.71 (17)	C15—O7—P1—O6	−160.0 (2)
O3—C9—C10—C11	−121.5 (2)	C15—O7—P1—C9	90.4 (2)
P1—C9—C10—C11	118.6 (2)	O3—C9—P1—O5	−57.93 (15)
O3—C9—C10—O4	61.2 (2)	C10—C9—P1—O5	64.71 (17)
P1—C9—C10—O4	−58.7 (2)	O3—C9—P1—O6	65.52 (14)
O4—C10—C11—C12	0.6 (3)	C10—C9—P1—O6	−171.84 (14)
C9—C10—C11—C12	−176.9 (2)	O3—C9—P1—O7	174.48 (12)
C10—C11—C12—C13	−0.6 (3)	C10—C9—P1—O7	−62.88 (16)
C11—C12—C13—O4	0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O5ⁱ	0.93	2.50	3.322 (3)	148
C9—H9···O2ⁱⁱ	0.98	2.35	3.270 (2)	157
C14—H14B···O5ⁱ	0.96	2.44	3.379 (3)	165

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅Cl₂O₇P
M_r	409.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	292
a, b, c (Å)	8.5380 (7), 17.3111 (14), 12.4003 (10)
β (°)	98.475 (1)
V (Å³)	1812.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12335, 4135, 3158
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.133, 1.05
No. of reflections	4135
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.31

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
C6—H6···O5ⁱ	0.93	2.50	3.322 (3)	147.5
C9—H9···O2ⁱⁱ	0.98	2.35	3.270 (2)	156.9
C14—H14B···O5ⁱ	0.96	2.44	3.379 (3)	164.7

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y+1, −z+1.

Acknowledgements

We gratefully acknowledge financial support of this work by the National Basic Research Program of China (grant No. 2010CB126100) and the National Natural Science Foundation of China (grant No. 20772042).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, T., Shen, P., Li, Y.-J. & He, H.-W. (2006). J. Fluorine Chem. 127, 291–295. Web of Science CrossRef CAS Google Scholar
He, H.-W. & Liu, Z.-J. (2001). Chin. J. Org. Chem. 21 878–883. CAS Google Scholar
He, H.-W., Wang, T. & Yuan, J.-L. (2005). J. Organomet. Chem. 690, 2608–2613. Web of Science CrossRef CAS Google Scholar
Peng, H., Wang, T., Xie, P., Chen, T., He, H.-W. & Wan, J. (2007). J. Agric. Food Chem. 55, 1871–1880. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar