Crystal structure of chlorfluazuron.

The title compound (systematic name: 1-{3,5-di-chloro-4-[3-chloro-5-(tri-fluoro-meth-yl)pyridin-2-yl-oxy]phen-yl}-3-(2,6-difluoro-benzo-yl)urea), C20H9Cl3F5N3O3, is a benzoyl-phenyl-urea insecticide. The dihedral angles between the planes of the central di-chloro-phenyl and the terminal di-fluoro-phenyl and chloro-pyridyl rings are 79.51 (6) and 78.84 6)°, respectively. In the crystal, pairs of N-H⋯O hydrogen bonds link adjacent mol-ecules, forming R 2 (2)(8) inversion dimers. In addition, the dimers are linked by short F⋯Cl [3.1060 (16) Å] and Cl⋯Cl [3.2837 (7) Å] contacts, as well as weak inter-molecular π-π inter-actions [ring centroid separation = 3.6100 (11) and 3.7764 (13) Å], resulting in a two-dimensional architecture parallel to (111).

Related literature

For information on the insecticidal properties of the title compound, see: Choi et al. (2011 ▸); Lee et al. (2013 ▸). For a related crystal structure, see: Jeon et al. (2014 ▸).

Experimental

Crystal data

C20H9Cl3F5N3O3

M = 540.65

Triclinic,

a = 8.5805 (3) Å

b = 10.1281 (4) Å

c = 12.5883 (4) Å

α = 79.498 (2)°

β = 82.930 (2)°

γ = 83.485 (2)°

V = 1062.82 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.51 mm−1

T = 173 K

0.28 × 0.12 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.872, T max = 0.975

19710 measured reflections

5259 independent reflections

4090 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.127

S = 1.06

5259 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2010 ▸); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014026632/sj5431sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026632/sj5431Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014026632/sj5431Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014026632/sj5431fig1.tif

The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Click here for additional data file.

a . DOI: 10.1107/S2056989014026632/sj5431fig2.tif

Crystal packing viewed along the a axis. The inter­molecular N—H⋯O hydrogen bonds, short F⋯Cl, Cl⋯Cl contacts and π–π inter­actions are shown as dashed lines.

CCDC reference: 1037499

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H9Cl3F5N3O3	Z = 2
Mr = 540.65	F(000) = 540
Triclinic, P1	Dx = 1.689 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5805 (3) Å	Cell parameters from 6417 reflections
b = 10.1281 (4) Å	θ = 2.4–28.1°
c = 12.5883 (4) Å	µ = 0.51 mm−1
α = 79.498 (2)°	T = 173 K
β = 82.930 (2)°	Plate, colourless
γ = 83.485 (2)°	0.28 × 0.12 × 0.05 mm
V = 1062.82 (7) Å3

Bruker APEXII CCD diffractometer	5259 independent reflections
Radiation source: fine-focus sealed tube	4090 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→10
Tmin = 0.872, Tmax = 0.975	k = −13→13
19710 measured reflections	l = −16→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0631P)2 + 0.4257P] where P = (Fo2 + 2Fc2)/3
5259 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.54 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
Cl1	0.51049 (7)	0.65788 (5)	0.51055 (4)	0.03275 (16)
Cl2	0.82607 (7)	1.05194 (6)	0.59008 (4)	0.03172 (15)
Cl3	0.64381 (7)	0.71391 (8)	0.88086 (5)	0.0459 (2)
F1	1.05653 (18)	1.14118 (18)	−0.13423 (14)	0.0590 (5)
F2	0.54499 (16)	1.35343 (16)	−0.10772 (12)	0.0470 (4)
F3	1.33225 (17)	0.60959 (17)	0.78423 (15)	0.0549 (5)
F4	1.28741 (18)	0.43892 (17)	0.72279 (14)	0.0552 (5)
F5	1.2067 (2)	0.4572 (2)	0.88756 (14)	0.0753 (7)
O1	0.86100 (19)	1.20897 (17)	0.06450 (12)	0.0347 (4)
O2	0.51802 (19)	0.94182 (16)	0.13689 (12)	0.0323 (4)
O3	0.66744 (16)	0.79859 (14)	0.64590 (11)	0.0237 (3)
N1	0.6634 (2)	1.09625 (17)	0.02702 (13)	0.0229 (4)
H1	0.6120	1.0859	−0.0268	0.027*
N2	0.6858 (2)	1.04878 (17)	0.21206 (13)	0.0218 (4)
H2	0.7469	1.1153	0.1963	0.026*
N3	0.9237 (2)	0.70890 (17)	0.60728 (14)	0.0245 (4)
C1	0.9398 (3)	1.2235 (2)	−0.1811 (2)	0.0323 (5)
C2	0.9644 (3)	1.2813 (3)	−0.2889 (2)	0.0382 (6)
H2A	1.0617	1.2633	−0.3309	0.046*
C3	0.8436 (3)	1.3662 (3)	−0.33402 (18)	0.0382 (6)
H3	0.8589	1.4080	−0.4080	0.046*
C4	0.7021 (3)	1.3915 (2)	−0.27473 (18)	0.0356 (6)
H4	0.6197	1.4502	−0.3066	0.043*
C5	0.6822 (3)	1.3296 (2)	−0.16762 (18)	0.0275 (5)
C6	0.7993 (2)	1.2441 (2)	−0.11733 (16)	0.0220 (4)
C7	0.7787 (2)	1.1828 (2)	0.00044 (16)	0.0228 (4)
C8	0.6163 (2)	1.0217 (2)	0.12916 (16)	0.0222 (4)
C9	0.6721 (2)	0.98326 (19)	0.32049 (15)	0.0190 (4)
C10	0.5976 (2)	0.86569 (19)	0.35643 (16)	0.0207 (4)
H10	0.5464	0.8274	0.3081	0.025*
C11	0.5998 (2)	0.80569 (19)	0.46473 (16)	0.0204 (4)
C12	0.6729 (2)	0.85890 (19)	0.53728 (15)	0.0202 (4)
C13	0.7419 (2)	0.9786 (2)	0.50062 (16)	0.0221 (4)
C14	0.7433 (2)	1.0399 (2)	0.39305 (16)	0.0221 (4)
H14	0.7929	1.1208	0.3685	0.026*
C15	0.8040 (2)	0.73051 (19)	0.67978 (16)	0.0192 (4)
C16	0.8070 (2)	0.6866 (2)	0.79131 (16)	0.0237 (4)
C17	0.9430 (2)	0.6189 (2)	0.82825 (17)	0.0258 (5)
H17	0.9492	0.5881	0.9037	0.031*
C18	1.0710 (2)	0.5965 (2)	0.75305 (17)	0.0235 (4)
C19	1.0565 (3)	0.6423 (2)	0.64440 (17)	0.0250 (4)
H19	1.1445	0.6262	0.5932	0.030*
C20	1.2233 (3)	0.5247 (2)	0.78821 (19)	0.0321 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0441 (3)	0.0284 (3)	0.0261 (3)	−0.0152 (2)	−0.0103 (2)	0.0063 (2)
Cl2	0.0376 (3)	0.0384 (3)	0.0237 (3)	−0.0096 (2)	−0.0131 (2)	−0.0067 (2)
Cl3	0.0296 (3)	0.0784 (5)	0.0193 (3)	0.0167 (3)	0.0006 (2)	0.0036 (3)
F1	0.0343 (8)	0.0660 (11)	0.0626 (11)	0.0190 (8)	0.0036 (8)	0.0059 (9)
F2	0.0289 (7)	0.0586 (9)	0.0402 (8)	0.0124 (7)	0.0018 (6)	0.0122 (7)
F3	0.0285 (8)	0.0604 (10)	0.0824 (13)	−0.0001 (7)	−0.0263 (8)	−0.0180 (9)
F4	0.0402 (9)	0.0576 (10)	0.0721 (12)	0.0233 (8)	−0.0194 (8)	−0.0305 (9)
F5	0.0415 (9)	0.1138 (16)	0.0434 (10)	0.0300 (10)	−0.0047 (8)	0.0351 (10)
O1	0.0393 (9)	0.0434 (9)	0.0243 (8)	−0.0195 (8)	−0.0120 (7)	0.0024 (7)
O2	0.0392 (9)	0.0394 (9)	0.0200 (8)	−0.0185 (7)	−0.0128 (7)	0.0059 (6)
O3	0.0189 (7)	0.0334 (8)	0.0160 (7)	0.0013 (6)	−0.0054 (6)	0.0030 (6)
N1	0.0234 (9)	0.0305 (9)	0.0154 (8)	−0.0070 (7)	−0.0089 (7)	0.0019 (7)
N2	0.0266 (9)	0.0222 (8)	0.0167 (8)	−0.0069 (7)	−0.0071 (7)	0.0022 (6)
N3	0.0261 (9)	0.0269 (9)	0.0188 (9)	0.0010 (7)	−0.0039 (7)	−0.0006 (7)
C1	0.0271 (12)	0.0321 (12)	0.0354 (13)	−0.0008 (9)	0.0004 (10)	−0.0039 (10)
C2	0.0398 (14)	0.0443 (14)	0.0311 (13)	−0.0145 (11)	0.0123 (11)	−0.0124 (11)
C3	0.0571 (16)	0.0417 (14)	0.0184 (11)	−0.0247 (12)	−0.0026 (11)	−0.0002 (10)
C4	0.0447 (14)	0.0369 (13)	0.0243 (12)	−0.0093 (11)	−0.0131 (11)	0.0071 (10)
C5	0.0247 (11)	0.0326 (11)	0.0233 (11)	−0.0045 (9)	−0.0030 (9)	0.0016 (9)
C6	0.0250 (11)	0.0219 (10)	0.0196 (10)	−0.0056 (8)	−0.0039 (8)	−0.0017 (8)
C7	0.0223 (10)	0.0246 (10)	0.0208 (10)	−0.0009 (8)	−0.0049 (8)	−0.0011 (8)
C8	0.0226 (10)	0.0248 (10)	0.0185 (10)	−0.0024 (8)	−0.0058 (8)	0.0006 (8)
C9	0.0181 (9)	0.0221 (9)	0.0159 (9)	0.0020 (7)	−0.0060 (7)	−0.0007 (7)
C10	0.0226 (10)	0.0225 (10)	0.0176 (10)	−0.0019 (8)	−0.0085 (8)	−0.0013 (8)
C11	0.0214 (10)	0.0177 (9)	0.0210 (10)	−0.0013 (7)	−0.0043 (8)	0.0008 (7)
C12	0.0202 (10)	0.0246 (10)	0.0142 (9)	0.0028 (8)	−0.0068 (8)	0.0015 (8)
C13	0.0219 (10)	0.0266 (10)	0.0200 (10)	−0.0006 (8)	−0.0090 (8)	−0.0063 (8)
C14	0.0229 (10)	0.0236 (10)	0.0201 (10)	−0.0052 (8)	−0.0056 (8)	−0.0009 (8)
C15	0.0180 (9)	0.0213 (9)	0.0185 (10)	−0.0019 (7)	−0.0065 (8)	−0.0007 (7)
C16	0.0231 (10)	0.0298 (11)	0.0168 (10)	0.0009 (8)	−0.0020 (8)	−0.0021 (8)
C17	0.0272 (11)	0.0321 (11)	0.0178 (10)	−0.0016 (9)	−0.0079 (9)	−0.0004 (8)
C18	0.0218 (10)	0.0251 (10)	0.0233 (10)	−0.0007 (8)	−0.0067 (8)	−0.0015 (8)
C19	0.0230 (10)	0.0295 (11)	0.0216 (10)	−0.0006 (8)	−0.0018 (8)	−0.0035 (8)
C20	0.0264 (11)	0.0389 (13)	0.0287 (12)	0.0045 (10)	−0.0069 (9)	−0.0020 (10)

Cl1—C11	1.7315 (19)	C2—H2A	0.9500
Cl2—C13	1.723 (2)	C3—C4	1.368 (4)
Cl3—C16	1.716 (2)	C3—H3	0.9500
F1—C1	1.350 (3)	C4—C5	1.378 (3)
F2—C5	1.340 (3)	C4—H4	0.9500
F3—C20	1.331 (3)	C5—C6	1.385 (3)
F4—C20	1.333 (3)	C6—C7	1.497 (3)
F5—C20	1.311 (3)	C9—C10	1.392 (3)
O1—C7	1.217 (2)	C9—C14	1.394 (3)
O2—C8	1.217 (2)	C10—C11	1.389 (3)
O3—C15	1.365 (2)	C10—H10	0.9500
O3—C12	1.390 (2)	C11—C12	1.384 (3)
N1—C7	1.366 (3)	C12—C13	1.387 (3)
N1—C8	1.405 (2)	C13—C14	1.382 (3)
N1—H1	0.8800	C14—H14	0.9500
N2—C8	1.347 (3)	C15—C16	1.396 (3)
N2—C9	1.402 (2)	C16—C17	1.373 (3)
N2—H2	0.8800	C17—C18	1.386 (3)
N3—C15	1.314 (3)	C17—H17	0.9500
N3—C19	1.347 (3)	C18—C19	1.378 (3)
C1—C2	1.377 (3)	C18—C20	1.497 (3)
C1—C6	1.381 (3)	C19—H19	0.9500
C2—C3	1.379 (4)
C15—O3—C12	116.53 (15)	C11—C10—H10	120.8
C7—N1—C8	128.40 (17)	C9—C10—H10	120.8
C7—N1—H1	115.8	C12—C11—C10	122.32 (18)
C8—N1—H1	115.8	C12—C11—Cl1	118.64 (15)
C8—N2—C9	127.54 (17)	C10—C11—Cl1	119.03 (15)
C8—N2—H2	116.2	C11—C12—C13	118.40 (17)
C9—N2—H2	116.2	C11—C12—O3	120.52 (17)
C15—N3—C19	117.22 (17)	C13—C12—O3	120.94 (17)
F1—C1—C2	119.5 (2)	C14—C13—C12	120.64 (18)
F1—C1—C6	117.4 (2)	C14—C13—Cl2	119.64 (15)
C2—C1—C6	123.2 (2)	C12—C13—Cl2	119.72 (15)
C1—C2—C3	118.0 (2)	C13—C14—C9	120.16 (18)
C1—C2—H2A	121.0	C13—C14—H14	119.9
C3—C2—H2A	121.0	C9—C14—H14	119.9
C4—C3—C2	121.5 (2)	N3—C15—O3	119.22 (17)
C4—C3—H3	119.2	N3—C15—C16	123.69 (18)
C2—C3—H3	119.2	O3—C15—C16	117.09 (18)
C3—C4—C5	118.4 (2)	C17—C16—C15	118.60 (19)
C3—C4—H4	120.8	C17—C16—Cl3	120.33 (16)
C5—C4—H4	120.8	C15—C16—Cl3	121.07 (16)
F2—C5—C4	119.4 (2)	C16—C17—C18	118.51 (19)
F2—C5—C6	117.64 (18)	C16—C17—H17	120.7
C4—C5—C6	122.9 (2)	C18—C17—H17	120.7
C1—C6—C5	116.01 (19)	C19—C18—C17	118.80 (19)
C1—C6—C7	121.58 (19)	C19—C18—C20	120.08 (19)
C5—C6—C7	122.35 (19)	C17—C18—C20	121.11 (19)
O1—C7—N1	124.57 (19)	N3—C19—C18	123.18 (19)
O1—C7—C6	121.15 (18)	N3—C19—H19	118.4
N1—C7—C6	114.27 (17)	C18—C19—H19	118.4
O2—C8—N2	125.62 (18)	F5—C20—F3	107.5 (2)
O2—C8—N1	119.61 (18)	F5—C20—F4	108.0 (2)
N2—C8—N1	114.76 (17)	F3—C20—F4	104.67 (19)
C10—C9—C14	120.10 (18)	F5—C20—C18	112.37 (19)
C10—C9—N2	123.68 (18)	F3—C20—C18	111.92 (19)
C14—C9—N2	116.18 (17)	F4—C20—C18	112.02 (19)
C11—C10—C9	118.32 (18)
F1—C1—C2—C3	−179.2 (2)	Cl1—C11—C12—O3	−3.3 (3)
C6—C1—C2—C3	1.5 (4)	C15—O3—C12—C11	107.5 (2)
C1—C2—C3—C4	−0.9 (4)	C15—O3—C12—C13	−77.0 (2)
C2—C3—C4—C5	−0.1 (4)	C11—C12—C13—C14	−2.7 (3)
C3—C4—C5—F2	179.6 (2)	O3—C12—C13—C14	−178.30 (18)
C3—C4—C5—C6	0.6 (4)	C11—C12—C13—Cl2	177.03 (16)
F1—C1—C6—C5	179.7 (2)	O3—C12—C13—Cl2	1.5 (3)
C2—C1—C6—C5	−1.0 (3)	C12—C13—C14—C9	1.4 (3)
F1—C1—C6—C7	2.6 (3)	Cl2—C13—C14—C9	−178.39 (15)
C2—C1—C6—C7	−178.1 (2)	C10—C9—C14—C13	0.8 (3)
F2—C5—C6—C1	−179.1 (2)	N2—C9—C14—C13	−177.08 (18)
C4—C5—C6—C1	−0.1 (3)	C19—N3—C15—O3	179.44 (17)
F2—C5—C6—C7	−2.0 (3)	C19—N3—C15—C16	−1.0 (3)
C4—C5—C6—C7	177.0 (2)	C12—O3—C15—N3	−9.7 (3)
C8—N1—C7—O1	0.0 (4)	C12—O3—C15—C16	170.78 (18)
C8—N1—C7—C6	179.18 (19)	N3—C15—C16—C17	1.1 (3)
C1—C6—C7—O1	60.5 (3)	O3—C15—C16—C17	−179.40 (18)
C5—C6—C7—O1	−116.5 (2)	N3—C15—C16—Cl3	−177.88 (16)
C1—C6—C7—N1	−118.8 (2)	O3—C15—C16—Cl3	1.6 (3)
C5—C6—C7—N1	64.3 (3)	C15—C16—C17—C18	−0.4 (3)
C9—N2—C8—O2	6.7 (4)	Cl3—C16—C17—C18	178.62 (16)
C9—N2—C8—N1	−174.42 (18)	C16—C17—C18—C19	−0.3 (3)
C7—N1—C8—O2	−175.0 (2)	C16—C17—C18—C20	179.3 (2)
C7—N1—C8—N2	6.1 (3)	C15—N3—C19—C18	0.3 (3)
C8—N2—C9—C10	8.7 (3)	C17—C18—C19—N3	0.3 (3)
C8—N2—C9—C14	−173.53 (19)	C20—C18—C19—N3	−179.2 (2)
C14—C9—C10—C11	−1.6 (3)	C19—C18—C20—F5	−163.0 (2)
N2—C9—C10—C11	176.18 (18)	C17—C18—C20—F5	17.4 (3)
C9—C10—C11—C12	0.1 (3)	C19—C18—C20—F3	76.0 (3)
C9—C10—C11—Cl1	−178.97 (15)	C17—C18—C20—F3	−103.6 (2)
C10—C11—C12—C13	2.0 (3)	C19—C18—C20—F4	−41.2 (3)
Cl1—C11—C12—C13	−178.89 (16)	C17—C18—C20—F4	139.2 (2)
C10—C11—C12—O3	177.58 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.88	1.96	2.837 (2)	175

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1O2i	0.88	1.96	2.837(2)	175

Symmetry code: (i) .