Crystal structure of flufenoxuron: a benzoyl-urea pesticide.

The title compound, C21H11ClF6N2O3 (systematic name: 1-{4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl}-3-(2,6-di-fluoro-benzo-yl)urea), is a benzoyl-urea pesticide. The dihedral angles between the central fluoro-benzene ring and the terminal di-fluoro-phenyl ring and chloro-phenyl ring system are 62.15 (5) and 88.03 (5)°, respectively. In the crystal, N-H⋯O hydrogen bonds link adjacent mol-ecules, forming R 2 (2)(8) inversion dimers that pack into loop chains along the a-axis direction by short F⋯F contacts [2.729 (2) Å]. In addition, the chains are linked by weak C-H⋯π and π-π inter-actions [inter-centroid distances = 3.661 (2) and 3.535 (12) Å], resulting in a three-dimensional architecture.

Related literature

For information on the toxicity and pesticidal properties of the title compound, see: Kamel et al. (2007 ▶); Salokhe et al. (2006 ▶). For a related crystal structure, see: Liu et al. (2008 ▶).

Experimental

Crystal data

C21H11ClF6N2O3

M = 488.77

Triclinic,

a = 10.017 (2) Å

b = 10.640 (2) Å

c = 10.677 (2) Å

α = 62.520 (9)°

β = 75.874 (8)°

γ = 81.831 (8)°

V = 978.4 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 173 K

0.35 × 0.30 × 0.28 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.908, T max = 0.926

14229 measured reflections

3822 independent reflections

3324 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 1.07

3822 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.30 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/S1600536814020649/su2781sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814020649/su2781Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814020649/su2781Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814020649/su2781fig1.tif

The mol­ecular structure of the title mol­ecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

b . DOI: 10.1107/S1600536814020649/su2781fig2.tif

Crystal packing of the title compound viewed along the b axis. The N—H⋯O hydrogen bonds, weak π⋯π inter­actions, and short F⋯F contacts are shown as dashed lines (see Table 1 for details).

CCDC reference: 1024205

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

C21H11ClF6N2O3	Z = 2
Mr = 488.77	F(000) = 492
Triclinic, P1	Dx = 1.659 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.017 (2) Å	Cell parameters from 8341 reflections
b = 10.640 (2) Å	θ = 2.2–28.4°
c = 10.677 (2) Å	µ = 0.28 mm−1
α = 62.520 (9)°	T = 173 K
β = 75.874 (8)°	Block, colourless
γ = 81.831 (8)°	0.35 × 0.30 × 0.28 mm
V = 978.4 (4) Å3

Bruker APEXII CCD diffractometer	3822 independent reflections
Radiation source: fine-focus sealed tube	3324 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.908, Tmax = 0.926	k = −13→13
14229 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.2919P] where P = (Fo2 + 2Fc2)/3
3822 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.30 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	1.05546 (6)	−0.22505 (6)	1.07307 (7)	0.06363 (18)
F1	0.72246 (14)	0.77531 (13)	0.68591 (13)	0.0641 (3)
F2	0.69987 (15)	0.81354 (13)	0.23893 (12)	0.0675 (4)
F3	0.60803 (12)	0.16340 (12)	0.85938 (13)	0.0628 (3)
F4	1.49311 (11)	−0.44174 (14)	0.79601 (15)	0.0679 (4)
F5	1.39871 (13)	−0.60799 (15)	0.79606 (16)	0.0717 (4)
F6	1.41608 (12)	−0.61650 (13)	0.99444 (13)	0.0641 (3)
N1	0.66935 (13)	0.55105 (12)	0.51095 (14)	0.0308 (3)
H1	0.5984	0.5943	0.4709	0.037*
N2	0.78988 (14)	0.33879 (13)	0.61862 (17)	0.0392 (3)
H2	0.8522	0.3912	0.6156	0.047*
O1	0.86135 (14)	0.59246 (13)	0.56208 (18)	0.0583 (4)
O2	0.59312 (11)	0.34257 (11)	0.55010 (13)	0.0374 (3)
O3	0.87566 (11)	−0.24450 (11)	0.90357 (13)	0.0390 (3)
C1	0.70453 (17)	0.85551 (18)	0.5500 (2)	0.0403 (4)
C2	0.67730 (18)	0.99811 (19)	0.5047 (2)	0.0499 (5)
H2A	0.6733	1.0404	0.5669	0.060*
C3	0.6561 (2)	1.07764 (19)	0.3669 (3)	0.0555 (5)
H3	0.6367	1.1766	0.3335	0.067*
C4	0.6621 (2)	1.0175 (2)	0.2763 (2)	0.0560 (5)
H4	0.6475	1.0735	0.1809	0.067*
C5	0.68988 (18)	0.87424 (18)	0.32706 (19)	0.0419 (4)
C6	0.71198 (15)	0.78873 (15)	0.46415 (18)	0.0339 (3)
C7	0.75540 (16)	0.63483 (16)	0.51697 (18)	0.0355 (4)
C8	0.68046 (15)	0.40302 (15)	0.56139 (16)	0.0296 (3)
C9	0.81003 (16)	0.18930 (15)	0.68433 (18)	0.0332 (3)
C10	0.92643 (16)	0.12655 (16)	0.63537 (19)	0.0384 (4)
H10	0.9899	0.1833	0.5515	0.046*
C11	0.95320 (16)	−0.01844 (17)	0.70618 (19)	0.0382 (4)
H11	1.0345	−0.0608	0.6719	0.046*
C12	0.86001 (16)	−0.09984 (15)	0.82683 (17)	0.0315 (3)
C13	0.74046 (17)	−0.04027 (17)	0.87751 (17)	0.0369 (4)
H13	0.6752	−0.0971	0.9593	0.044*
C14	0.71953 (17)	0.10336 (17)	0.80564 (18)	0.0370 (4)
C15	1.00506 (16)	−0.30610 (15)	0.88616 (16)	0.0324 (3)
C16	1.03725 (17)	−0.37490 (16)	0.79989 (17)	0.0365 (4)
H16	0.9738	−0.3717	0.7452	0.044*
C17	1.16171 (17)	−0.44842 (17)	0.79308 (17)	0.0366 (4)
H17	1.1843	−0.4958	0.7335	0.044*
C18	1.25330 (16)	−0.45299 (16)	0.87284 (17)	0.0340 (3)
C19	1.22220 (17)	−0.38360 (17)	0.95874 (18)	0.0372 (4)
H19	1.2857	−0.3865	1.0132	0.045*
C20	1.09787 (17)	−0.31014 (16)	0.96449 (18)	0.0368 (4)
C21	1.38909 (18)	−0.53102 (19)	0.8653 (2)	0.0426 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0639 (3)	0.0762 (4)	0.0827 (4)	0.0180 (3)	−0.0260 (3)	−0.0621 (3)
F1	0.0877 (9)	0.0590 (7)	0.0562 (7)	−0.0061 (6)	−0.0288 (6)	−0.0267 (6)
F2	0.1045 (10)	0.0538 (7)	0.0453 (6)	−0.0072 (7)	−0.0209 (7)	−0.0190 (5)
F3	0.0616 (7)	0.0458 (6)	0.0604 (7)	0.0227 (5)	0.0026 (6)	−0.0204 (5)
F4	0.0379 (6)	0.0673 (8)	0.0858 (9)	−0.0064 (5)	0.0052 (6)	−0.0309 (7)
F5	0.0624 (8)	0.0797 (9)	0.1068 (10)	0.0300 (7)	−0.0318 (7)	−0.0716 (8)
F6	0.0514 (7)	0.0652 (7)	0.0604 (7)	0.0206 (6)	−0.0210 (6)	−0.0168 (6)
N1	0.0298 (6)	0.0220 (6)	0.0409 (7)	0.0023 (5)	−0.0152 (5)	−0.0113 (5)
N2	0.0356 (7)	0.0221 (6)	0.0619 (9)	0.0018 (5)	−0.0261 (7)	−0.0132 (6)
O1	0.0441 (7)	0.0319 (6)	0.1053 (12)	0.0034 (5)	−0.0421 (8)	−0.0241 (7)
O2	0.0350 (6)	0.0266 (5)	0.0551 (7)	0.0012 (4)	−0.0212 (5)	−0.0168 (5)
O3	0.0319 (6)	0.0237 (5)	0.0490 (7)	0.0025 (4)	−0.0073 (5)	−0.0071 (5)
C1	0.0345 (8)	0.0365 (8)	0.0518 (10)	−0.0056 (7)	−0.0105 (7)	−0.0191 (8)
C2	0.0396 (9)	0.0396 (10)	0.0765 (14)	−0.0066 (8)	−0.0031 (9)	−0.0336 (10)
C3	0.0423 (10)	0.0263 (8)	0.0855 (15)	−0.0017 (7)	−0.0064 (10)	−0.0175 (9)
C4	0.0546 (12)	0.0350 (9)	0.0571 (12)	−0.0039 (8)	−0.0148 (9)	−0.0003 (9)
C5	0.0435 (9)	0.0342 (8)	0.0445 (9)	−0.0045 (7)	−0.0098 (8)	−0.0133 (7)
C6	0.0285 (7)	0.0256 (7)	0.0453 (9)	−0.0039 (6)	−0.0094 (7)	−0.0122 (7)
C7	0.0324 (8)	0.0265 (7)	0.0471 (9)	−0.0016 (6)	−0.0133 (7)	−0.0132 (7)
C8	0.0294 (7)	0.0242 (7)	0.0339 (7)	0.0005 (6)	−0.0088 (6)	−0.0110 (6)
C9	0.0333 (8)	0.0243 (7)	0.0448 (9)	0.0018 (6)	−0.0196 (7)	−0.0128 (7)
C10	0.0292 (8)	0.0287 (8)	0.0473 (9)	−0.0035 (6)	−0.0087 (7)	−0.0075 (7)
C11	0.0285 (8)	0.0289 (8)	0.0487 (9)	0.0026 (6)	−0.0056 (7)	−0.0122 (7)
C12	0.0331 (8)	0.0230 (7)	0.0380 (8)	0.0025 (6)	−0.0137 (6)	−0.0110 (6)
C13	0.0357 (8)	0.0327 (8)	0.0359 (8)	0.0018 (7)	−0.0055 (7)	−0.0115 (7)
C14	0.0368 (8)	0.0345 (8)	0.0410 (9)	0.0092 (7)	−0.0111 (7)	−0.0192 (7)
C15	0.0324 (8)	0.0219 (7)	0.0353 (8)	0.0018 (6)	−0.0083 (6)	−0.0065 (6)
C16	0.0411 (9)	0.0320 (8)	0.0347 (8)	−0.0004 (7)	−0.0149 (7)	−0.0102 (7)
C17	0.0427 (9)	0.0324 (8)	0.0348 (8)	−0.0006 (7)	−0.0069 (7)	−0.0156 (7)
C18	0.0351 (8)	0.0259 (7)	0.0352 (8)	−0.0006 (6)	−0.0058 (7)	−0.0095 (6)
C19	0.0351 (8)	0.0358 (8)	0.0441 (9)	0.0018 (7)	−0.0131 (7)	−0.0190 (7)
C20	0.0416 (9)	0.0299 (8)	0.0412 (9)	0.0003 (7)	−0.0088 (7)	−0.0179 (7)
C21	0.0379 (9)	0.0400 (9)	0.0488 (10)	0.0031 (7)	−0.0074 (8)	−0.0207 (8)

Cl1—C20	1.7214 (17)	C4—C5	1.373 (3)
F1—C1	1.344 (2)	C4—H4	0.9500
F2—C5	1.345 (2)	C5—C6	1.375 (2)
F3—C14	1.3444 (19)	C6—C7	1.501 (2)
F4—C21	1.339 (2)	C9—C10	1.372 (2)
F5—C21	1.315 (2)	C9—C14	1.380 (2)
F6—C21	1.325 (2)	C10—C11	1.389 (2)
N1—C7	1.3566 (19)	C10—H10	0.9500
N1—C8	1.4070 (18)	C11—C12	1.376 (2)
N1—H1	0.8800	C11—H11	0.9500
N2—C8	1.331 (2)	C12—C13	1.383 (2)
N2—C9	1.4180 (19)	C13—C14	1.369 (2)
N2—H2	0.8800	C13—H13	0.9500
O1—C7	1.214 (2)	C15—C16	1.378 (2)
O2—C8	1.2152 (18)	C15—C20	1.379 (2)
O3—C12	1.3767 (18)	C16—C17	1.379 (2)
O3—C15	1.3776 (18)	C16—H16	0.9500
C1—C2	1.371 (2)	C17—C18	1.378 (2)
C1—C6	1.379 (2)	C17—H17	0.9500
C2—C3	1.370 (3)	C18—C19	1.380 (2)
C2—H2A	0.9500	C18—C21	1.494 (2)
C3—C4	1.371 (3)	C19—C20	1.377 (2)
C3—H3	0.9500	C19—H19	0.9500
C7—N1—C8	127.52 (12)	C12—C11—C10	118.92 (15)
C7—N1—H1	116.2	C12—C11—H11	120.5
C8—N1—H1	116.2	C10—C11—H11	120.5
C8—N2—C9	122.64 (13)	C11—C12—O3	123.56 (14)
C8—N2—H2	118.7	C11—C12—C13	121.33 (14)
C9—N2—H2	118.7	O3—C12—C13	115.09 (13)
C12—O3—C15	118.26 (12)	C14—C13—C12	117.68 (15)
F1—C1—C2	118.69 (17)	C14—C13—H13	121.2
F1—C1—C6	117.85 (15)	C12—C13—H13	121.2
C2—C1—C6	123.45 (17)	F3—C14—C13	118.10 (15)
C3—C2—C1	117.89 (18)	F3—C14—C9	118.80 (14)
C3—C2—H2A	121.1	C13—C14—C9	123.05 (15)
C1—C2—H2A	121.1	O3—C15—C16	119.66 (14)
C2—C3—C4	121.44 (17)	O3—C15—C20	120.24 (14)
C2—C3—H3	119.3	C16—C15—C20	119.85 (14)
C4—C3—H3	119.3	C15—C16—C17	119.88 (15)
C3—C4—C5	118.30 (19)	C15—C16—H16	120.1
C3—C4—H4	120.8	C17—C16—H16	120.1
C5—C4—H4	120.8	C18—C17—C16	119.86 (15)
F2—C5—C4	119.35 (17)	C18—C17—H17	120.1
F2—C5—C6	117.60 (15)	C16—C17—H17	120.1
C4—C5—C6	123.02 (18)	C17—C18—C19	120.59 (15)
C5—C6—C1	115.89 (15)	C17—C18—C21	120.41 (15)
C5—C6—C7	123.76 (15)	C19—C18—C21	118.99 (15)
C1—C6—C7	120.09 (15)	C20—C19—C18	119.12 (15)
O1—C7—N1	124.19 (14)	C20—C19—H19	120.4
O1—C7—C6	120.04 (14)	C18—C19—H19	120.4
N1—C7—C6	115.76 (13)	C19—C20—C15	120.69 (15)
O2—C8—N2	124.43 (14)	C19—C20—Cl1	120.01 (13)
O2—C8—N1	119.65 (13)	C15—C20—Cl1	119.28 (12)
N2—C8—N1	115.91 (12)	F5—C21—F6	107.35 (15)
C10—C9—C14	117.81 (14)	F5—C21—F4	106.12 (15)
C10—C9—N2	120.57 (14)	F6—C21—F4	105.84 (15)
C14—C9—N2	121.43 (14)	F5—C21—C18	112.98 (15)
C9—C10—C11	121.19 (15)	F6—C21—C18	112.64 (14)
C9—C10—H10	119.4	F4—C21—C18	111.43 (14)
C11—C10—H10	119.4
F1—C1—C2—C3	−178.48 (16)	C15—O3—C12—C11	19.0 (2)
C6—C1—C2—C3	0.2 (3)	C15—O3—C12—C13	−162.55 (14)
C1—C2—C3—C4	−0.2 (3)	C11—C12—C13—C14	−1.7 (2)
C2—C3—C4—C5	0.2 (3)	O3—C12—C13—C14	179.82 (14)
C3—C4—C5—F2	−178.29 (18)	C12—C13—C14—F3	−175.87 (15)
C3—C4—C5—C6	−0.1 (3)	C12—C13—C14—C9	1.6 (3)
F2—C5—C6—C1	178.30 (15)	C10—C9—C14—F3	176.97 (15)
C4—C5—C6—C1	0.1 (3)	N2—C9—C14—F3	2.0 (2)
F2—C5—C6—C7	4.2 (2)	C10—C9—C14—C13	−0.5 (2)
C4—C5—C6—C7	−174.03 (16)	N2—C9—C14—C13	−175.52 (15)
F1—C1—C6—C5	178.56 (15)	C12—O3—C15—C16	−101.84 (17)
C2—C1—C6—C5	−0.1 (2)	C12—O3—C15—C20	83.96 (18)
F1—C1—C6—C7	−7.1 (2)	O3—C15—C16—C17	−173.73 (14)
C2—C1—C6—C7	174.21 (15)	C20—C15—C16—C17	0.5 (2)
C8—N1—C7—O1	3.9 (3)	C15—C16—C17—C18	0.1 (2)
C8—N1—C7—C6	−175.67 (14)	C16—C17—C18—C19	−0.6 (2)
C5—C6—C7—O1	121.8 (2)	C16—C17—C18—C21	−179.38 (15)
C1—C6—C7—O1	−52.1 (2)	C17—C18—C19—C20	0.4 (2)
C5—C6—C7—N1	−58.6 (2)	C21—C18—C19—C20	179.20 (15)
C1—C6—C7—N1	127.49 (16)	C18—C19—C20—C15	0.3 (2)
C9—N2—C8—O2	−5.5 (3)	C18—C19—C20—Cl1	178.96 (12)
C9—N2—C8—N1	174.92 (14)	O3—C15—C20—C19	173.50 (14)
C7—N1—C8—O2	178.80 (15)	C16—C15—C20—C19	−0.7 (2)
C7—N1—C8—N2	−1.6 (2)	O3—C15—C20—Cl1	−5.2 (2)
C8—N2—C9—C10	122.32 (18)	C16—C15—C20—Cl1	−179.39 (12)
C8—N2—C9—C14	−62.8 (2)	C17—C18—C21—F5	−9.8 (2)
C14—C9—C10—C11	−0.6 (2)	C19—C18—C21—F5	171.34 (15)
N2—C9—C10—C11	174.45 (15)	C17—C18—C21—F6	−131.67 (17)
C9—C10—C11—C12	0.6 (3)	C19—C18—C21—F6	49.5 (2)
C10—C11—C12—O3	179.01 (15)	C17—C18—C21—F4	109.55 (18)
C10—C11—C12—C13	0.6 (3)	C19—C18—C21—F4	−69.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.88	1.97	2.8157 (17)	161
C2—H2A···Cg2ii	0.95	2.89	3.661 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.88	1.97	2.8157 (17)	161
C2—H2A⋯Cg2ii	0.95	2.89	3.661 (2)	139

Symmetry codes: (i) ; (ii) .