Ethyl 4-{2,6-dichloro-4-[3-(2,6-difluoro-benzo-yl)ureido]phen-oxy}butanoate.

The title compound, C(20)H(18)Cl(2)F(2)N(2)O(5), is considered to belong to the fourth generation of insecticides with properties such as high selectivity, low acute toxicity for mammals and high biological activity. An intramolecular N-H⋯O hydrogen bond results in the formation of a six-membered ring. In the crystal structure, intermolecular N-H⋯O and C-H⋯F hydrogen bonds link the molecules.

Related literature

For related literature, see: Wang et al. (1998 ▶, 1999 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H18Cl2F2N2O5

M = 475.26

Monoclinic,

a = 11.262 (2) Å

b = 10.463 (2) Å

c = 18.613 (4) Å

β = 98.78 (3)°

V = 2167.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 293 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.872, T max = 0.933

4157 measured reflections

3944 independent reflections

2385 reflections with I > 2σ(I)

R int = 0.041

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.290

S = 1.13

3944 reflections

268 parameters

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −0.99 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024987/cs2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024987/cs2088Isup2.hkl

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

C20H18Cl2F2N2O5	F000 = 976
Mr = 475.26	Dx = 1.456 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.262 (2) Å	θ = 9–12º
b = 10.463 (2) Å	µ = 0.35 mm−1
c = 18.613 (4) Å	T = 293 (2) K
β = 98.78 (3)º	Block, colourless
V = 2167.5 (8) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.041
Radiation source: fine-focus sealed tube	θmax = 25.3º
Monochromator: graphite	θmin = 2.0º
T = 293(2) K	h = −13→13
ω/2θ scans	k = 0→12
Absorption correction: ψ scan(North et al., 1968)	l = 0→22
Tmin = 0.872, Tmax = 0.933	3 standard reflections
4157 measured reflections	every 200 reflections
3944 independent reflections	intensity decay: none
2385 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.082	H-atom parameters constrained
wR(F2) = 0.290	w = 1/[σ2(Fo2) + (0.1372P)2 + 4.2262P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
3944 reflections	Δρmax = 0.77 e Å−3
268 parameters	Δρmin = −0.99 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. (North et al., 1968)

	x	y	z	Uiso*/Ueq
Cl1	0.23061 (14)	0.09615 (16)	0.16895 (10)	0.0611 (5)
Cl2	0.02268 (15)	−0.30602 (15)	0.02019 (10)	0.0672 (6)
F1	−0.5092 (6)	0.3204 (6)	0.2109 (3)	0.127 (2)
F2	−0.5604 (4)	0.3418 (6)	−0.0403 (2)	0.0995 (17)
N1	−0.2177 (4)	0.0877 (5)	0.0826 (3)	0.0473 (12)
H1A	−0.2132	0.1606	0.1042	0.057*
O1	0.5929 (5)	0.0111 (5)	0.2331 (3)	0.0813 (16)
C1	0.7375 (8)	0.1501 (10)	0.2970 (5)	0.095
H1B	0.7622	0.1938	0.3421	0.142*
H1C	0.7173	0.2116	0.2588	0.142*
H1D	0.8019	0.0969	0.2861	0.142*
N2	−0.4207 (4)	0.1420 (5)	0.0532 (3)	0.0481 (12)
H2A	−0.4908	0.1202	0.0316	0.058*
O2	0.4801 (5)	−0.1199 (6)	0.2895 (3)	0.092
C2	0.6371 (8)	0.0743 (9)	0.3027 (4)	0.092 (3)
H2B	0.5738	0.1271	0.3170	0.110*
H2C	0.6583	0.0100	0.3400	0.110*
O3	0.2254 (3)	−0.1568 (4)	0.09703 (19)	0.0458 (10)
C3	0.5158 (6)	−0.0854 (7)	0.2341 (3)	0.0544 (16)
O4	−0.3529 (4)	−0.0477 (4)	0.0170 (2)	0.0578 (12)
C4	0.4795 (5)	−0.1407 (6)	0.1610 (4)	0.0545 (16)
H4A	0.5512	−0.1638	0.1411	0.065*
H4B	0.4376	−0.0757	0.1297	0.065*
O5	−0.3196 (4)	0.3054 (5)	0.1175 (3)	0.0775 (16)
C5	0.3991 (5)	−0.2578 (6)	0.1597 (4)	0.0513 (15)
H5A	0.4037	−0.3058	0.1156	0.062*
H5B	0.4293	−0.3121	0.2006	0.062*
C6	0.2705 (5)	−0.2267 (6)	0.1628 (3)	0.0436 (13)
H6A	0.2246	−0.3046	0.1655	0.052*
H6B	0.2640	−0.1751	0.2053	0.052*
C7	0.1154 (5)	−0.1029 (6)	0.0964 (3)	0.0419 (13)
C8	0.1028 (5)	0.0189 (6)	0.1269 (3)	0.0431 (13)
C9	−0.0055 (5)	0.0791 (6)	0.1230 (3)	0.0455 (14)
H9A	−0.0108	0.1591	0.1440	0.055*
C10	−0.1091 (5)	0.0182 (5)	0.0867 (3)	0.0440 (14)
C11	−0.1009 (5)	−0.1023 (5)	0.0560 (3)	0.0453 (14)
H11A	−0.1688	−0.1437	0.0323	0.054*
C12	0.0113 (5)	−0.1586 (5)	0.0618 (3)	0.0464 (14)
C13	−0.3273 (5)	0.0529 (6)	0.0489 (3)	0.0428 (13)
C14	−0.4138 (6)	0.2591 (6)	0.0874 (3)	0.0509 (15)
C15	−0.5308 (5)	0.3250 (5)	0.0855 (3)	0.0431 (13)
C16	−0.5738 (7)	0.3548 (7)	0.1491 (4)	0.0622 (18)
C17	−0.6834 (8)	0.4151 (7)	0.1493 (5)	0.076 (2)
H17A	−0.7108	0.4325	0.1930	0.091*
C18	−0.7493 (7)	0.4481 (7)	0.0858 (5)	0.074 (2)
H18A	−0.8236	0.4871	0.0854	0.089*
C19	−0.7083 (6)	0.4251 (7)	0.0223 (4)	0.071 (2)
H19A	−0.7535	0.4498	−0.0215	0.085*
C20	−0.6010 (6)	0.3657 (7)	0.0230 (3)	0.0574 (17)

	U11	U22	U33	U12	U13	U23
Cl1	0.0473 (9)	0.0581 (10)	0.0746 (11)	−0.0088 (7)	−0.0015 (7)	−0.0205 (8)
Cl2	0.0649 (11)	0.0426 (9)	0.0892 (13)	0.0079 (8)	−0.0042 (9)	−0.0222 (8)
F1	0.181 (6)	0.146 (5)	0.057 (3)	0.081 (5)	0.027 (3)	0.020 (3)
F2	0.104 (3)	0.145 (5)	0.048 (2)	0.052 (3)	0.006 (2)	−0.015 (3)
N1	0.047 (3)	0.041 (3)	0.050 (3)	0.010 (2)	−0.007 (2)	−0.010 (2)
O1	0.092 (4)	0.072 (3)	0.068 (3)	−0.033 (3)	−0.024 (3)	0.011 (3)
C1	0.095	0.095	0.095	0.000	0.014	0.000
N2	0.048 (3)	0.038 (3)	0.056 (3)	0.009 (2)	0.001 (2)	−0.010 (2)
O2	0.092	0.092	0.092	0.000	0.014	0.000
C2	0.109 (7)	0.085 (6)	0.068 (5)	−0.039 (5)	−0.029 (5)	−0.001 (4)
O3	0.042 (2)	0.058 (3)	0.038 (2)	0.0023 (19)	0.0072 (16)	−0.0027 (18)
C3	0.055 (4)	0.060 (4)	0.047 (4)	−0.001 (3)	0.006 (3)	0.015 (3)
O4	0.048 (2)	0.041 (2)	0.077 (3)	0.0065 (19)	−0.015 (2)	−0.021 (2)
C4	0.045 (3)	0.056 (4)	0.063 (4)	−0.008 (3)	0.009 (3)	−0.001 (3)
O5	0.053 (3)	0.058 (3)	0.111 (4)	0.000 (2)	−0.020 (3)	−0.034 (3)
C5	0.038 (3)	0.052 (4)	0.063 (4)	0.002 (3)	0.008 (3)	−0.001 (3)
C6	0.043 (3)	0.042 (3)	0.045 (3)	0.003 (3)	0.004 (2)	0.001 (3)
C7	0.041 (3)	0.048 (3)	0.036 (3)	0.002 (3)	0.004 (2)	0.004 (3)
C8	0.046 (3)	0.043 (3)	0.040 (3)	−0.009 (3)	0.004 (2)	−0.003 (3)
C9	0.052 (3)	0.043 (3)	0.039 (3)	0.002 (3)	0.001 (3)	−0.008 (3)
C10	0.047 (3)	0.040 (3)	0.041 (3)	0.002 (3)	−0.004 (2)	−0.001 (3)
C11	0.045 (3)	0.038 (3)	0.051 (3)	0.002 (3)	−0.001 (3)	−0.006 (3)
C12	0.054 (3)	0.035 (3)	0.049 (3)	0.001 (3)	0.005 (3)	0.000 (3)
C13	0.040 (3)	0.043 (3)	0.043 (3)	0.011 (3)	−0.004 (2)	−0.003 (3)
C14	0.053 (4)	0.046 (4)	0.051 (4)	0.001 (3)	0.003 (3)	−0.002 (3)
C15	0.044 (3)	0.037 (3)	0.049 (3)	−0.005 (2)	0.008 (3)	−0.001 (3)
C16	0.091 (5)	0.051 (4)	0.049 (4)	0.010 (4)	0.024 (4)	0.011 (3)
C17	0.101 (6)	0.055 (4)	0.085 (6)	0.026 (4)	0.056 (5)	0.005 (4)
C18	0.060 (4)	0.050 (4)	0.114 (7)	0.015 (3)	0.020 (4)	−0.022 (4)
C19	0.062 (4)	0.073 (5)	0.074 (5)	0.016 (4)	0.001 (4)	−0.019 (4)
C20	0.059 (4)	0.061 (4)	0.050 (4)	0.007 (3)	−0.002 (3)	−0.018 (3)

Cl1—C8	1.730 (6)	C4—H4B	0.9700
Cl2—C12	1.739 (6)	O5—C14	1.222 (7)
F1—C16	1.314 (9)	C5—C6	1.494 (8)
F2—C20	1.350 (7)	C5—H5A	0.9700
N1—C13	1.347 (7)	C5—H5B	0.9700
N1—C10	1.414 (7)	C6—H6A	0.9700
N1—H1A	0.8600	C6—H6B	0.9700
O1—C3	1.333 (8)	C7—C12	1.379 (8)
O1—C2	1.472 (9)	C7—C8	1.410 (8)
C1—C2	1.399 (11)	C8—C9	1.365 (8)
C1—H1B	0.9600	C9—C10	1.408 (8)
C1—H1C	0.9600	C9—H9A	0.9300
C1—H1D	0.9600	C10—C11	1.394 (8)
N2—C14	1.378 (8)	C11—C12	1.383 (8)
N2—C13	1.417 (7)	C11—H11A	0.9300
N2—H2A	0.8600	C14—C15	1.482 (8)
O2—C3	1.217 (8)	C15—C20	1.372 (9)
C2—H2B	0.9700	C15—C16	1.381 (8)
C2—H2C	0.9700	C16—C17	1.386 (10)
O3—C7	1.360 (6)	C17—C18	1.342 (11)
O3—C6	1.449 (7)	C17—H17A	0.9300
C3—C4	1.477 (9)	C18—C19	1.354 (10)
O4—C13	1.223 (7)	C18—H18A	0.9300
C4—C5	1.522 (9)	C19—C20	1.358 (9)
C4—H4A	0.9700	C19—H19A	0.9300
C13—N1—C10	127.6 (5)	O3—C7—C8	121.3 (5)
C13—N1—H1A	116.2	C12—C7—C8	116.1 (5)
C10—N1—H1A	116.2	C9—C8—C7	122.6 (5)
C3—O1—C2	117.4 (6)	C9—C8—Cl1	118.9 (4)
C2—C1—H1B	109.5	C7—C8—Cl1	118.4 (4)
C2—C1—H1C	109.5	C8—C9—C10	119.1 (5)
H1B—C1—H1C	109.5	C8—C9—H9A	120.5
C2—C1—H1D	109.5	C10—C9—H9A	120.5
H1B—C1—H1D	109.5	C11—C10—C9	120.2 (5)
H1C—C1—H1D	109.5	C11—C10—N1	123.7 (5)
C14—N2—C13	128.4 (5)	C9—C10—N1	116.1 (5)
C14—N2—H2A	115.8	C12—C11—C10	118.1 (5)
C13—N2—H2A	115.8	C12—C11—H11A	121.0
C1—C2—O1	110.9 (8)	C10—C11—H11A	121.0
C1—C2—H2B	109.5	C7—C12—C11	123.9 (5)
O1—C2—H2B	109.5	C7—C12—Cl2	117.9 (5)
C1—C2—H2C	109.5	C11—C12—Cl2	118.1 (5)
O1—C2—H2C	109.5	O4—C13—N1	126.2 (5)
H2B—C2—H2C	108.1	O4—C13—N2	118.2 (5)
C7—O3—C6	114.7 (4)	N1—C13—N2	115.6 (5)
O2—C3—O1	122.5 (7)	O5—C14—N2	123.3 (6)
O2—C3—C4	125.6 (6)	O5—C14—C15	122.2 (6)
O1—C3—C4	111.9 (5)	N2—C14—C15	114.5 (5)
C3—C4—C5	114.3 (6)	C20—C15—C16	115.1 (6)
C3—C4—H4A	108.7	C20—C15—C14	124.0 (5)
C5—C4—H4A	108.7	C16—C15—C14	120.8 (6)
C3—C4—H4B	108.7	F1—C16—C15	117.9 (6)
C5—C4—H4B	108.7	F1—C16—C17	119.7 (6)
H4A—C4—H4B	107.6	C15—C16—C17	122.3 (7)
C6—C5—C4	113.7 (5)	C18—C17—C16	119.2 (7)
C6—C5—H5A	108.8	C18—C17—H17A	120.4
C4—C5—H5A	108.8	C16—C17—H17A	120.4
C6—C5—H5B	108.8	C17—C18—C19	120.4 (7)
C4—C5—H5B	108.8	C17—C18—H18A	119.8
H5A—C5—H5B	107.7	C19—C18—H18A	119.8
O3—C6—C5	107.1 (5)	C18—C19—C20	119.7 (7)
O3—C6—H6A	110.3	C18—C19—H19A	120.1
C5—C6—H6A	110.3	C20—C19—H19A	120.1
O3—C6—H6B	110.3	F2—C20—C19	119.8 (6)
C5—C6—H6B	110.3	F2—C20—C15	117.1 (6)
H6A—C6—H6B	108.5	C19—C20—C15	123.2 (6)
O3—C7—C12	122.4 (5)
C3—O1—C2—C1	165.2 (8)	C10—C11—C12—C7	0.4 (9)
C2—O1—C3—O2	1.5 (10)	C10—C11—C12—Cl2	−177.4 (4)
C2—O1—C3—C4	−179.5 (7)	C10—N1—C13—O4	2.0 (10)
O2—C3—C4—C5	−5.6 (10)	C10—N1—C13—N2	−179.6 (5)
O1—C3—C4—C5	175.5 (5)	C14—N2—C13—O4	178.4 (6)
C3—C4—C5—C6	79.5 (7)	C14—N2—C13—N1	−0.2 (9)
C7—O3—C6—C5	−169.7 (5)	C13—N2—C14—O5	3.4 (10)
C4—C5—C6—O3	64.3 (7)	C13—N2—C14—C15	−176.1 (5)
C6—O3—C7—C12	−99.1 (6)	O5—C14—C15—C20	116.7 (8)
C6—O3—C7—C8	85.8 (6)	N2—C14—C15—C20	−63.8 (8)
O3—C7—C8—C9	175.6 (5)	O5—C14—C15—C16	−60.2 (9)
C12—C7—C8—C9	0.3 (8)	N2—C14—C15—C16	119.3 (6)
O3—C7—C8—Cl1	−2.8 (7)	C20—C15—C16—F1	−178.7 (7)
C12—C7—C8—Cl1	−178.2 (4)	C14—C15—C16—F1	−1.5 (10)
C7—C8—C9—C10	−0.5 (9)	C20—C15—C16—C17	3.5 (10)
Cl1—C8—C9—C10	177.9 (4)	C14—C15—C16—C17	−179.3 (6)
C8—C9—C10—C11	0.7 (9)	F1—C16—C17—C18	−179.1 (8)
C8—C9—C10—N1	−178.0 (5)	C15—C16—C17—C18	−1.3 (12)
C13—N1—C10—C11	−1.2 (9)	C16—C17—C18—C19	−1.3 (12)
C13—N1—C10—C9	177.4 (6)	C17—C18—C19—C20	1.4 (12)
C9—C10—C11—C12	−0.6 (9)	C18—C19—C20—F2	179.5 (7)
N1—C10—C11—C12	178.0 (5)	C18—C19—C20—C15	1.1 (11)
O3—C7—C12—C11	−175.5 (5)	C16—C15—C20—F2	178.1 (6)
C8—C7—C12—C11	−0.2 (9)	C14—C15—C20—F2	1.0 (10)
O3—C7—C12—Cl2	2.2 (8)	C16—C15—C20—C19	−3.4 (10)
C8—C7—C12—Cl2	177.5 (4)	C14—C15—C20—C19	179.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4i	0.86	2.00	2.856 (6)	173
C5—H5A···F2ii	0.97	2.44	3.201 (8)	135
N1—H1A···O5	0.86	1.97	2.675 (7)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4i	0.86	2.00	2.856 (6)	173
C5—H5A⋯F2ii	0.97	2.44	3.201 (8)	135
N1—H1A⋯O5	0.86	1.97	2.675 (7)	138

Symmetry codes: (i) ; (ii) .