Ethyl 4-{2,6-dichloro-4-[3-(2,6-difluoro­benzo­yl)ureido]phen­oxy}butanoate

Liu, Y.-H.; Li, F.-S.; Li, Y.; Yu, D.-S.; Lu, C.

doi:10.1107/S1600536808024987

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1729

doi:10.1107/S1600536808024987

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Ethyl 4-{2,6-dichloro-4-[3-(2,6-difluorobenzoyl)ureido]phenoxy}butanoate

Yin-Hong Liu,^a Fang-Shi Li,^a ^* Yi Li,^a Da-Sheng Yu ^a and Chui Lu ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technolgy, Xinmofan Road No. 5, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: fangshi.li@njut.edu.cn

(Received 16 July 2008; accepted 3 August 2008; online 9 August 2008)

The title compound, C₂₀H₁₈Cl₂F₂N₂O₅, 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_r = 475.26
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.082
wR(F²) = 0.290
S = 1.13
3944 reflections
268 parameters
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.99 e Å⁻³

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) -x-1, -y, -z; (ii) -x, -y, -z.

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.

Supporting information

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

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

checkCIF report

Comment top

The title compound is generally recognized as an insect growth regulator that interferes with chitin synthesis in target pests, causing death or abortive development (Wang et al. 1998). Bonding dimensions conform to expected values (Allen et al., 1987).

Related literature top

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

Experimental top

The title compound was prepared according to a literature method (Wang et al. 1999). The crystals suitable for X-ray analysis were obtained by dissolving it (0.1 g) in acetonitrile (25 ml) and evaporating the solvent slowly at room temperature for about 6 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. N—H···O intramolecular hydrogen bond is shown by dashed line.
	Fig. 2. A packing diagram detail from the crystal structure. N—H···O and C—H···F intermolecular hydrogen bonds are shown by dashed lines.

Ethyl 4-{2,6-dichloro-4-[3-(2,6-difluorobenzoyl)ureido]phenoxy}butanoate top

Crystal data top

C₂₀H₁₈Cl₂F₂N₂O₅	F(000) = 976
M_r = 475.26	D_x = 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 = 9–12°
b = 10.463 (2) Å	µ = 0.35 mm⁻¹
c = 18.613 (4) Å	T = 293 K
β = 98.78 (3)°	Block, colourless
V = 2167.5 (8) Å³	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 25.3°, θ_min = 2.0°
ω/2θ scans	h = −13→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
T_min = 0.872, T_max = 0.933	l = 0→22
4157 measured reflections	3 standard reflections every 200 reflections
3944 independent reflections	intensity decay: none

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.290	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.1372P)² + 4.2262P] where P = (F_o² + 2F_c²)/3
3944 reflections	(Δ/σ)_max < 0.001
268 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.99 e Å⁻³

Crystal data top

C₂₀H₁₈Cl₂F₂N₂O₅	V = 2167.5 (8) Å³
M_r = 475.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.262 (2) Å	µ = 0.35 mm⁻¹
b = 10.463 (2) Å	T = 293 K
c = 18.613 (4) Å	0.40 × 0.30 × 0.20 mm
β = 98.78 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2385 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.041
T_min = 0.872, T_max = 0.933	3 standard reflections every 200 reflections
4157 measured reflections	intensity decay: none
3944 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.290	H-atom parameters constrained
S = 1.13	Δρ_max = 0.77 e Å⁻³
3944 reflections	Δρ_min = −0.99 e Å⁻³
268 parameters

Special details top

Experimental. (North et al., 1968)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x−1, −y, −z; (ii) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈Cl₂F₂N₂O₅
M_r	475.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.262 (2), 10.463 (2), 18.613 (4)
β (°)	98.78 (3)
V (Å³)	2167.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.872, 0.933
No. of measured, independent and observed [I > 2σ(I)] reflections	4157, 3944, 2385
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.290, 1.13
No. of reflections	3944
No. of parameters	268
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.99

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cl1—C8	1.730 (6)	N2—C14	1.378 (8)
Cl2—C12	1.739 (6)	N2—C13	1.417 (7)
F1—C16	1.314 (9)	O2—C3	1.217 (8)
F2—C20	1.350 (7)	O3—C7	1.360 (6)
N1—C13	1.347 (7)	O3—C6	1.449 (7)
N1—C10	1.414 (7)	O4—C13	1.223 (7)
O1—C3	1.333 (8)	O5—C14	1.222 (7)
O1—C2	1.472 (9)

C13—N1—C10	127.6 (5)	C9—C10—N1	116.1 (5)
C10—N1—H1A	116.2	C7—C12—Cl2	117.9 (5)
C3—O1—C2	117.4 (6)	C11—C12—Cl2	118.1 (5)
C1—C2—O1	110.9 (8)	O4—C13—N1	126.2 (5)
C7—O3—C6	114.7 (4)	O4—C13—N2	118.2 (5)
O2—C3—O1	122.5 (7)	N1—C13—N2	115.6 (5)
O2—C3—C4	125.6 (6)	O5—C14—N2	123.3 (6)
O1—C3—C4	111.9 (5)	O5—C14—C15	122.2 (6)
O3—C6—C5	107.1 (5)	N2—C14—C15	114.5 (5)
O3—C7—C12	122.4 (5)	F1—C16—C15	117.9 (6)
O3—C7—C8	121.3 (5)	F1—C16—C17	119.7 (6)
C9—C8—Cl1	118.9 (4)	F2—C20—C19	119.8 (6)
C7—C8—Cl1	118.4 (4)	F2—C20—C15	117.1 (6)
C11—C10—N1	123.7 (5)

Hydrogen-bond geometry (Å, º) top

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) −x−1, −y, −z; (ii) −x, −y, −z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, S., Allan, R. D., Skerritt, J. H. & Kennedy, I. R. (1998). J. Agric. Food Chem. 46, 3330–3338. Web of Science CrossRef CAS Google Scholar
Wang, S., Allan, R. D., Skerritt, J. H. & Kennedy, I. R. (1999). J. Agric. Food Chem. 47, 3416–3424. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 64| Part 9| September 2008| Page o1729

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