(Dimeth-oxy-phosphor-yl)(furan-2-yl)methyl 2-(2,4-dichloro-phen-oxy)acetate.

In the title compound, C(15)H(15)Cl(2)O(7)P, the benzene and furan rings form a dihedral angle of 73.54 (1)°. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules 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 = 409.14

Monoclinic,

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 ▶); 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.

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

C15H15Cl2O7P	F(000) = 840
Mr = 409.14	Dx = 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

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

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(Fo2) + (0.0672P)2 + 0.2806P] where P = (Fo2 + 2Fc2)/3
4135 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .