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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2962.
Published online 2010 October 30. doi:  10.1107/S1600536810042820
PMCID: PMC3009241

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

Abstract

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 [triangle], 2005 [triangle]); Chen et al. (2006 [triangle]). The synthesis and biological activity of the title compound have been discussed by Peng et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2962-scheme1.jpg

Experimental

Crystal data

  • C15H15Cl2O7P
  • M r = 409.14
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2962-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.133
  • S = 1.05
  • 4135 reflections
  • 228 parameters
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042820/cv2778Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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).

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All hydrogen atoms were geometrically positioned [C—H 0.93-0.98 Å], and refined as riding, with Uiso(H) = 1.2-1.5 Ueq(C).

Figures

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.

Crystal data

C15H15Cl2O7PF(000) = 840
Mr = 409.14Dx = 1.499 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4066 reflections
a = 8.5380 (7) Åθ = 2.4–28.2°
b = 17.3111 (14) ŵ = 0.48 mm1
c = 12.4003 (10) ÅT = 292 K
β = 98.475 (1)°Block, colourless
V = 1812.8 (3) Å30.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer3158 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
graphiteθmax = 27.5°, θmin = 2.0°
phi and ω scansh = −11→11
12335 measured reflectionsk = −22→19
4135 independent reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0672P)2 + 0.2806P] where P = (Fo2 + 2Fc2)/3
4135 reflections(Δ/σ)max = 0.001
228 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = −0.31 e Å3

Special details

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)

xyzUiso*/Ueq
C10.6128 (3)0.35463 (14)0.10119 (19)0.0489 (5)
C20.4929 (3)0.40648 (14)0.10635 (19)0.0545 (6)
H20.43500.42620.04290.065*
C30.4592 (3)0.42900 (14)0.20734 (19)0.0474 (5)
C40.5448 (2)0.40033 (12)0.30291 (17)0.0377 (4)
C50.6644 (2)0.34767 (12)0.29467 (18)0.0411 (5)
H50.72200.32740.35780.049*
C60.7000 (3)0.32463 (13)0.1940 (2)0.0459 (5)
H60.78120.28960.18920.055*
C70.5786 (2)0.39588 (13)0.49683 (17)0.0412 (5)
H7A0.57470.34000.49220.049*
H7B0.52270.41160.55590.049*
C80.7491 (2)0.42157 (12)0.52171 (16)0.0361 (4)
C90.9975 (2)0.39109 (12)0.62871 (16)0.0361 (4)
H91.02690.43440.58490.043*
C101.0363 (2)0.41187 (12)0.74493 (17)0.0390 (5)
C111.1050 (3)0.47563 (13)0.78872 (19)0.0449 (5)
H111.13520.51860.75170.054*
C121.1229 (3)0.46505 (18)0.9034 (2)0.0631 (7)
H121.16840.49980.95600.076*
C131.0633 (3)0.39691 (18)0.9214 (2)0.0642 (7)
H131.05930.37570.98980.077*
C141.1220 (4)0.35140 (18)0.3883 (2)0.0681 (8)
H14A1.08620.40320.39760.102*
H14B1.08670.33480.31490.102*
H14C1.23550.34990.40260.102*
C151.3707 (3)0.3126 (2)0.7176 (2)0.0762 (9)
H15A1.34910.35170.76840.114*
H15B1.48100.31380.71040.114*
H15C1.34420.26280.74380.114*
Cl10.65651 (11)0.32723 (5)−0.02623 (6)0.0777 (3)
Cl20.30927 (9)0.49516 (5)0.21544 (6)0.0819 (3)
O10.50190 (16)0.42765 (9)0.39781 (12)0.0444 (4)
O20.80530 (19)0.47377 (9)0.47743 (14)0.0548 (4)
O30.82710 (15)0.37669 (8)0.59892 (11)0.0394 (3)
O41.0077 (2)0.36170 (10)0.82338 (14)0.0610 (5)
O51.0513 (2)0.23366 (9)0.64065 (14)0.0552 (4)
O61.0582 (2)0.30095 (10)0.46306 (13)0.0546 (4)
O71.27695 (17)0.32711 (10)0.61288 (14)0.0510 (4)
P11.09650 (6)0.30439 (3)0.58986 (5)0.04063 (17)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0557 (13)0.0517 (14)0.0399 (12)−0.0049 (11)0.0090 (10)−0.0065 (10)
C20.0591 (14)0.0644 (16)0.0368 (13)0.0079 (12)−0.0036 (11)0.0024 (11)
C30.0411 (11)0.0545 (13)0.0442 (13)0.0110 (10)−0.0014 (10)0.0008 (11)
C40.0301 (9)0.0439 (11)0.0377 (11)−0.0011 (8)0.0003 (8)−0.0009 (9)
C50.0352 (10)0.0446 (12)0.0415 (12)0.0010 (9)−0.0015 (9)0.0027 (9)
C60.0425 (11)0.0432 (12)0.0522 (14)0.0026 (9)0.0082 (10)−0.0050 (10)
C70.0357 (10)0.0517 (13)0.0356 (11)−0.0018 (9)0.0031 (8)0.0030 (9)
C80.0373 (10)0.0402 (11)0.0301 (10)−0.0008 (8)0.0023 (8)−0.0016 (8)
C90.0308 (9)0.0402 (11)0.0362 (11)−0.0047 (8)0.0018 (8)0.0062 (9)
C100.0356 (10)0.0443 (12)0.0369 (11)0.0040 (9)0.0046 (9)0.0037 (9)
C110.0509 (13)0.0404 (12)0.0436 (13)−0.0089 (10)0.0070 (10)−0.0034 (10)
C120.0587 (15)0.0773 (19)0.0502 (15)0.0000 (14)−0.0022 (12)−0.0206 (14)
C130.0732 (17)0.084 (2)0.0352 (13)0.0139 (16)0.0064 (12)0.0061 (13)
C140.0799 (19)0.088 (2)0.0378 (14)−0.0214 (16)0.0133 (13)0.0000 (13)
C150.0442 (14)0.116 (3)0.0642 (19)0.0139 (15)−0.0057 (13)0.0160 (17)
Cl10.1028 (6)0.0855 (5)0.0477 (4)0.0091 (4)0.0213 (4)−0.0122 (3)
Cl20.0755 (5)0.1100 (6)0.0563 (4)0.0552 (4)−0.0029 (3)0.0040 (4)
O10.0355 (7)0.0607 (10)0.0353 (8)0.0096 (7)−0.0004 (6)−0.0011 (7)
O20.0500 (9)0.0558 (10)0.0541 (10)−0.0142 (8)−0.0072 (7)0.0202 (8)
O30.0322 (7)0.0458 (8)0.0389 (8)−0.0049 (6)0.0004 (6)0.0105 (6)
O40.0774 (12)0.0568 (11)0.0505 (10)−0.0025 (9)0.0147 (9)0.0053 (8)
O50.0657 (10)0.0453 (9)0.0558 (10)−0.0021 (8)0.0123 (8)0.0066 (8)
O60.0633 (10)0.0619 (10)0.0387 (9)−0.0138 (8)0.0074 (8)−0.0046 (7)
O70.0370 (8)0.0686 (11)0.0468 (9)0.0026 (7)0.0043 (7)0.0063 (8)
P10.0402 (3)0.0448 (3)0.0369 (3)−0.0021 (2)0.0060 (2)0.0002 (2)

Geometric parameters (Å, °)

C1—C21.370 (3)C9—H90.9800
C1—C61.377 (3)C10—C111.328 (3)
C1—Cl11.742 (2)C10—O41.353 (2)
C2—C31.382 (3)C11—C121.419 (3)
C2—H20.9300C11—H110.9300
C3—C41.389 (3)C12—C131.317 (4)
C3—Cl21.732 (2)C12—H120.9300
C4—O11.367 (2)C13—O41.380 (3)
C4—C51.384 (3)C13—H130.9300
C5—C61.386 (3)C14—O61.438 (3)
C5—H50.9300C14—H14A0.9600
C6—H60.9300C14—H14B0.9600
C7—O11.415 (2)C14—H14C0.9600
C7—C81.509 (3)C15—O71.444 (3)
C7—H7A0.9700C15—H15A0.9600
C7—H7B0.9700C15—H15B0.9600
C8—O21.194 (2)C15—H15C0.9600
C8—O31.333 (2)O5—P11.4548 (16)
C9—O31.468 (2)O6—P11.5591 (17)
C9—C101.475 (3)O7—P11.5749 (16)
C9—P11.822 (2)
C2—C1—C6121.6 (2)C11—C10—C9128.6 (2)
C2—C1—Cl1118.84 (19)O4—C10—C9120.50 (19)
C6—C1—Cl1119.56 (19)C10—C11—C12106.2 (2)
C1—C2—C3118.9 (2)C10—C11—H11126.9
C1—C2—H2120.5C12—C11—H11126.9
C3—C2—H2120.5C13—C12—C11107.3 (2)
C2—C3—C4121.3 (2)C13—C12—H12126.3
C2—C3—Cl2119.57 (18)C11—C12—H12126.3
C4—C3—Cl2119.15 (18)C12—C13—O4109.7 (2)
O1—C4—C5125.83 (19)C12—C13—H13125.1
O1—C4—C3115.91 (19)O4—C13—H13125.1
C5—C4—C3118.3 (2)O6—C14—H14A109.5
C4—C5—C6121.2 (2)O6—C14—H14B109.5
C4—C5—H5119.4H14A—C14—H14B109.5
C6—C5—H5119.4O6—C14—H14C109.5
C1—C6—C5118.7 (2)H14A—C14—H14C109.5
C1—C6—H6120.6H14B—C14—H14C109.5
C5—C6—H6120.6O7—C15—H15A109.5
O1—C7—C8111.83 (16)O7—C15—H15B109.5
O1—C7—H7A109.2H15A—C15—H15B109.5
C8—C7—H7A109.2O7—C15—H15C109.5
O1—C7—H7B109.2H15A—C15—H15C109.5
C8—C7—H7B109.2H15B—C15—H15C109.5
H7A—C7—H7B107.9C4—O1—C7117.64 (16)
O2—C8—O3125.38 (18)C8—O3—C9116.97 (15)
O2—C8—C7124.74 (19)C10—O4—C13105.9 (2)
O3—C8—C7109.87 (17)C14—O6—P1125.73 (16)
O3—C9—C10111.03 (15)C15—O7—P1121.16 (16)
O3—C9—P1105.95 (13)O5—P1—O6112.02 (9)
C10—C9—P1114.39 (14)O5—P1—O7116.52 (10)
O3—C9—H9108.4O6—P1—O7104.26 (9)
C10—C9—H9108.4O5—P1—C9114.57 (9)
P1—C9—H9108.4O6—P1—C9105.17 (9)
C11—C10—O4110.8 (2)O7—P1—C9103.06 (9)
C6—C1—C2—C30.0 (4)C5—C4—O1—C7−4.5 (3)
Cl1—C1—C2—C3−179.22 (19)C3—C4—O1—C7175.69 (18)
C1—C2—C3—C40.2 (4)C8—C7—O1—C471.0 (2)
C1—C2—C3—Cl2179.42 (19)O2—C8—O3—C9−2.4 (3)
C2—C3—C4—O1179.2 (2)C7—C8—O3—C9176.68 (16)
Cl2—C3—C4—O10.0 (3)C10—C9—O3—C8119.82 (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—C13177.36 (19)
C3—C4—C5—C60.8 (3)C12—C13—O4—C100.0 (3)
C2—C1—C6—C50.2 (4)C14—O6—P1—O5−163.4 (2)
Cl1—C1—C6—C5179.39 (16)C14—O6—P1—O7−36.6 (2)
C4—C5—C6—C1−0.6 (3)C14—O6—P1—C971.5 (2)
O1—C7—C8—O214.4 (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—C990.4 (2)
P1—C9—C10—C11118.6 (2)O3—C9—P1—O5−57.93 (15)
O3—C9—C10—O461.2 (2)C10—C9—P1—O564.71 (17)
P1—C9—C10—O4−58.7 (2)O3—C9—P1—O665.52 (14)
O4—C10—C11—C120.6 (3)C10—C9—P1—O6−171.84 (14)
C9—C10—C11—C12−176.9 (2)O3—C9—P1—O7174.48 (12)
C10—C11—C12—C13−0.6 (3)C10—C9—P1—O7−62.88 (16)
C11—C12—C13—O40.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O5i0.932.503.322 (3)148
C9—H9···O2ii0.982.353.270 (2)157
C14—H14B···O5i0.962.443.379 (3)165

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2778).

References

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

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