Crystal structure of flufenoxuron: a benzoyl­urea pesticide

Jeon, Y.; Kang, G.; Lee, S.; Kim, T.H.

doi:10.1107/S1600536814020649

Crystal structure of flufenoxuron: a benzoylurea pesticide

The title compound, C₂₁H₁₁ClF₆N₂O₃ (systematic name: 1-{4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl}-3-(2,6-difluorobenzoyl)urea), is a benzoylurea pesticide. The dihedral angles between the central fluorobenzene ring and the terminal difluorophenyl ring and chlorophenyl ring system are 62.15 (5) and 88.03 (5)°, respectively. In the crystal, N—H

O hydrogen bonds link adjacent molecules, forming R₂²(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 interactions [inter-centroid distances = 3.661 (2) and 3.535 (12) Å], resulting in a three-dimensional architecture.

Keywords: crystal structure; benzoylurea; pesticide; N—H

O hydrogen bonds; C—H

π interactions; π–π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536814020649/su2781sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536814020649/su2781Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536814020649/su2781Isup3.cml Supplementary material

CCDC reference: 1024205

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.038
wR factor = 0.108
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C1     -C6            1.37 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.053 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         13 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT242_ALERT_2_G Low       Ueq as Compared to Neighbors for .....        C21 Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact  F2     ..  F5      .       2.73 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         11 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

Comment top

Flufenoxuron is a benzoylurea pesticide and acts as an insect growth regulator and chitin synthesis inhibitor. It is used to control immature stages of insects and phytophagous mites on fruits and vegetables (Salokhe et al., 2006; Kamel et al., 2007) and its crystal structure is reported on herein.

In th e title compound, Fig. 1, the dihedral angles between the central fluorobenzene ring and the terminal difluorophenyl ring and chlorophenyl ring system are 62.15 (5) and 88.03 (5)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in the crystal structure of a similar compound (Liu et al., 2008).

In the crystal, Fig. 2, molecules are linked by a a pair of urea N—H···O hydrogen bonds (Table 1), forming inversion dimers with an R₂²(8) ring motif. In addition, a short F···F contact [F2···F5ⁱ, 2.729 (2) Å] links the dimers into one-dimensional chains extending along [100]. In addition, a weak intermolecular C—H···π interaction [C2—H2A···Cg2ⁱⁱ, 3.611 (2) Å] and π–π interaction between the terminal chlorophenyl ring systems [Cg3···Cg3ⁱⁱⁱ, 3.535 (12) Å] are present (Cg2 and Cg3 are the centroids of the C9-C14 and C15-C20 rings, respectively) [for symmetry codes: (i), -x + 1, -y + 1, -z + 1, (ii), x, y + 1, z, and (iii), -x + 2, -y + 1, -z + 2].

Related literature top

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 top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH₂Cl₂ gave single crystals suitable for X-ray analysis.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. 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).

1-{4-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl}-3-(2,6-difluorobenzoyl)urea top

Crystal data top

C₂₁H₁₁ClF₆N₂O₃	Z = 2
M_r = 488.77	F(000) = 492
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0571P)² + 0.2919P] where P = (F_o² + 2F_c²)/3
3822 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₁H₁₁ClF₆N₂O₃	γ = 81.831 (8)°
M_r = 488.77	V = 978.4 (4) Å³
Triclinic, P1	Z = 2
a = 10.017 (2) Å	Mo Kα radiation
b = 10.640 (2) Å	µ = 0.28 mm⁻¹
c = 10.677 (2) Å	T = 173 K
α = 62.520 (9)°	0.35 × 0.30 × 0.28 mm
β = 75.874 (8)°

Data collection top

Bruker APEXII CCD diffractometer	3822 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3324 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.926	R_int = 0.023
14229 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.07	Δρ_max = 0.27 e Å⁻³
3822 reflections	Δρ_min = −0.30 e Å⁻³
298 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) x, y+1, z.