Crystal structure of N-{4-[(6-chloro­pyridin-3-yl)meth­oxy]phen­yl}-2,6-di­fluoro­benzamide

Liang, Y.; Shi, L.-Q.; Yang, Z.-W.

doi:10.1107/S2056989015023701

research communications

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ISSN: 2056-9890

Volume 72| Part 1| January 2016| Pages 60-62

doi:10.1107/S2056989015023701

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Crystal structure of N-{4-[(6-chloropyridin-3-yl)methoxy]phenyl}-2,6-difluorobenzamide

Ying Liang,^a ^* Li-Qiao Shi ^a and Zi-Wen Yang ^a

^aHubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Science, Wuhan 430064, People's Republic of China
^*Correspondence e-mail: ying.liang@nberc.com

Edited by J. Simpson, University of Otago, New Zealand (Received 30 November 2015; accepted 10 December 2015; online 1 January 2016)

In the title compound, C₁₉H₁₃ClF₂N₂O₂, the conformation of the N—H bond in the amide segment is anti to the C=O bond. The molecule is not planar, with dihedral angles between the central benzene ring and the outer benzene and pyridyl rings of 73.35 (7) and 81.26 (6)°, respectively. A weak intramolecular C—H⋯O hydrogen bond occurs. In the crystal, N—H⋯N, C—H⋯O and C—H⋯F hydrogen bonds lead to the formation of dimers. The N—H⋯N inversion dimers are linked by π–π contacts between adjacent pyridine rings [centroid–centroid = 3.8541 (12) Å] and C—H⋯π interactions. These contacts combine to stack the molecules along the a axis.

Keywords: crystal structure; amide derivative; pyridine; hydrogen bonding; π–π contacts.

CCDC reference: 1441555

1. Chemical context

Amide derivatives show diverse biological properties, acting as insecticides (Liu et al., 2004a ), fungicides (Liu et al., 2004b ) and acaricides (Shiga et al., 2003 ). Amides in regular commercial use include benzamide (flutolanil, fluopicolide), nicotinamide (boscalid) and thiazole carboxamide (thifluzamide, ethaboxam). As a part of our work on the synthesis of novel fluorine-containing compounds with good biological activities, we report herein on the crystal structure of the title compound,(I), Fig. 1.

Figure 1
The structure of (I)

, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

2. Structural commentary

The conformation of the N—H and the C=O bonds in the amide segment are anti to one another, similar to the conformation observed in another amide compound (Gowda et al., 2010 ). The dihedral angle between the two benzene rings is 73.35 (6)° while that between the central benzene ring and the chloro-substituted pyridine ring is 81.26 (6). The amide residue C1/N1/C7/O1 lies close to the plane of the central benzene ring, making a dihedral angle of 8.73 (6)°. A weak intramolecular C9—H9⋯O1 hydrogen bond (Table 1) contributes to the planarity of this part of the molecule.

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1	0.93	2.27	2.863 (2)	121
N1—H1⋯N2ⁱ	0.88 (2)	2.24 (2)	3.109 (2)	170.6 (18)
C19—H19⋯F2ⁱⁱ	0.93	2.54	3.309 (2)	140
C14—H14B⋯O1ⁱⁱ	0.97	2.42	3.344 (3)	160
C16—H16⋯Cg2ⁱⁱⁱ	0.93	2.99	3.912 (2)	173
Symmetry codes: (i) -x, -y+1, -z; (ii) x-1, y, z; (iii) x-1, y, z+1.

3. Supramolecular features

In the crystal structure, pairs of classical N1—H1⋯N2ⁱ hydrogen bonds, Table 1, link the molecules into inversion dimers and generate R₂²(22) rings (Bernstein et al., 1995 ). C14—H14B⋯O1ⁱⁱ and C19—H19⋯F2ⁱⁱ hydrogen bonds also form dimers, which enclose an R₂²(10) ring motif, Fig. 2. The N—H⋯N dimers are linked into chains along the c-axis direction by π–π stacking interactions between adjacent pyridyl rings [Cg1⋯Cg1^iv = 3.8541 (12) Å; symmetry code: (iv) 1 − x, 1 − y, 1 − z] augmented by a weak C16—H16⋯Cg2 contact (Cg2 is the centroid of the C1–C6 benzene ring), Table 1, Fig. 3. These contacts combine to stack the molecules along the a axis, Fig. 4.

Figure 2
A pair of dimers with hydrogen bonds drawn as blue dashed lines.

Figure 3
Chains of inversion dimers along the c-axis direction. Hydrogen bonds are drawn as dashed lines with π–π and C—H⋯π contacts shown as green dotted lines.

Figure 4
The overall packing for (I)

viewed along the a-axis direction.

4. Synthesis and crystallization

Triethylamine (6mmol) was added dropwise to a stirred solution of 4-(6-chloropyridin-3-yl) methoxy aniline (5mmol) and 2,6-difluorobenzoyl chloride (5mmol) in dry dichloromethane (20ml) at 275-277 K. The mixture was stirred at 283–288 K for 2 h, then washed with 0.5% hydrochloric acid solution, and a saturated aqueous solution of sodium hydrogen carbonate, dried and evaporated. The residue was recrystallized from dichloromethane, giving colourless blocks of the title compound after three weeks.

5. Database survey

A search of the Cambridge Structural Database (Version 5.36 with three updates) (Groom & Allen, 2014 ) for N-(4-(pyridin-3-ylmethoxy)phenyl)benzamide or its substituted derivatives gave no hits. However, structures of eight substituted 2,6-difluoro-N-phenylbenzamide derivatives were found, see for example Cockroft et al. (2007 ); Spitaleri et al. (2004 ); Fun et al. (2010 ). Two structures of purely organic 3-(phenoxymethyl)pyridine derivatives have also been reported (Lakshminarayana et al., 2009 ; Liu et al., 2010 ) together with that of a cadmium complex of 4-[(6-chloropyridin-3-yl)methoxy]benzoate, Li et al. (2007 ).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The NH H atom was located in a difference Fourier map and freely refined. The C-bound H atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93–0.97 Å and U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₃ClF₂N₂O₂
M_r	374.76
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	298
a, b, c (Å)	8.8173 (11), 10.7036 (13), 10.8452 (14)
α, β, γ (°)	61.939 (2), 77.597 (2), 69.636 (2)
V (Å³)	845.15 (18)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.26
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001 )
T_min, T_max	0.959, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	5474, 3271, 2886
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.116, 1.06
No. of reflections	3271
No. of parameters	239
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23
Computer programs: SMART and SAINT (Bruker, 2000 ), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Supporting information

CCDC reference: 1441555

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015023701/sj5486sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015023701/sj5486Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015023701/sj5486Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

N-{4-[(6-Chloropyridin-3-yl)methoxy]phenyl}-2,6-difluorobenzamide top

Crystal data top

C₁₉H₁₃ClF₂N₂O₂	Z = 2
M_r = 374.76	F(000) = 384
Triclinic, P1	D_x = 1.473 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8173 (11) Å	Cell parameters from 2810 reflections
b = 10.7036 (13) Å	θ = 2.3–28.3°
c = 10.8452 (14) Å	µ = 0.26 mm⁻¹
α = 61.939 (2)°	T = 298 K
β = 77.597 (2)°	Block, colorless
γ = 69.636 (2)°	0.16 × 0.12 × 0.10 mm
V = 845.15 (18) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3271 independent reflections
Radiation source: fine-focus sealed tube	2886 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
T_min = 0.959, T_max = 0.974	k = −13→13
5474 measured reflections	l = −12→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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0526P)² + 0.196P] where P = (F_o² + 2F_c²)/3
3271 reflections	(Δ/σ)_max < 0.001
239 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.7630 (2)	0.2167 (2)	−0.02643 (18)	0.0427 (4)
C2	0.8270 (2)	0.1167 (2)	−0.08394 (19)	0.0478 (4)
C3	0.9422 (3)	0.1317 (3)	−0.1918 (2)	0.0611 (6)
H3	0.9816	0.0618	−0.2276	0.073*
C4	0.9982 (3)	0.2526 (3)	−0.2461 (2)	0.0706 (7)
H4	1.0773	0.2644	−0.3195	0.085*
C5	0.9403 (3)	0.3566 (3)	−0.1949 (2)	0.0750 (7)
H5	0.9787	0.4388	−0.2327	0.090*
C6	0.8239 (3)	0.3360 (2)	−0.0861 (2)	0.0602 (5)
C7	0.6521 (2)	0.1886 (2)	0.10413 (18)	0.0432 (4)
C8	0.3644 (2)	0.21024 (17)	0.18987 (17)	0.0391 (4)
C9	0.3813 (2)	0.1688 (2)	0.32952 (18)	0.0462 (4)
H9	0.4817	0.1503	0.3590	0.055*
C10	0.2489 (2)	0.1551 (2)	0.42425 (18)	0.0461 (4)
H10	0.2609	0.1273	0.5176	0.055*
C11	0.0990 (2)	0.18196 (17)	0.38294 (18)	0.0408 (4)
C12	0.0809 (2)	0.2233 (2)	0.24416 (19)	0.0470 (4)
H12	−0.0198	0.2422	0.2149	0.056*
C13	0.2140 (2)	0.2363 (2)	0.14935 (18)	0.0461 (4)
H13	0.2019	0.2631	0.0563	0.055*
C14	−0.1851 (2)	0.2030 (2)	0.4525 (2)	0.0497 (5)
H14A	−0.2488	0.1521	0.5341	0.060*
H14B	−0.1861	0.1737	0.3806	0.060*
C15	−0.2607 (2)	0.36755 (19)	0.40005 (18)	0.0414 (4)
C16	−0.2680 (2)	0.4370 (2)	0.4829 (2)	0.0498 (5)
H16	−0.2264	0.3819	0.5710	0.060*
C17	−0.3362 (2)	0.5864 (2)	0.4347 (2)	0.0506 (5)
H17	−0.3418	0.6348	0.4885	0.061*
C18	−0.3961 (2)	0.6622 (2)	0.3043 (2)	0.0479 (4)
C19	−0.3260 (2)	0.4551 (2)	0.2721 (2)	0.0503 (5)
H19	−0.3230	0.4098	0.2161	0.060*
Cl1	−0.48341 (8)	0.85162 (6)	0.23999 (7)	0.0783 (2)
F1	0.77345 (18)	−0.00346 (13)	−0.02627 (13)	0.0741 (4)
F2	0.7661 (2)	0.43493 (16)	−0.03160 (16)	0.1031 (6)
N1	0.49454 (18)	0.22686 (16)	0.08547 (16)	0.0430 (4)
H1	0.468 (2)	0.265 (2)	−0.001 (2)	0.052*
N2	−0.3942 (2)	0.60203 (18)	0.22226 (16)	0.0537 (4)
O1	0.71012 (17)	0.1345 (2)	0.21658 (15)	0.0727 (5)
O2	−0.02172 (15)	0.16015 (14)	0.48849 (13)	0.0495 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0410 (9)	0.0482 (10)	0.0375 (9)	−0.0112 (8)	−0.0013 (7)	−0.0189 (8)
C2	0.0514 (11)	0.0483 (10)	0.0415 (10)	−0.0084 (8)	−0.0054 (8)	−0.0207 (8)
C3	0.0524 (12)	0.0763 (15)	0.0463 (11)	0.0010 (11)	−0.0033 (9)	−0.0335 (11)
C4	0.0484 (12)	0.116 (2)	0.0456 (12)	−0.0288 (13)	0.0066 (9)	−0.0342 (13)
C5	0.0860 (17)	0.1005 (19)	0.0517 (13)	−0.0615 (15)	0.0073 (12)	−0.0240 (13)
C6	0.0785 (15)	0.0630 (13)	0.0489 (11)	−0.0310 (11)	0.0043 (10)	−0.0278 (10)
C7	0.0470 (10)	0.0465 (9)	0.0385 (9)	−0.0125 (8)	−0.0001 (8)	−0.0220 (8)
C8	0.0434 (9)	0.0330 (8)	0.0364 (9)	−0.0069 (7)	0.0014 (7)	−0.0159 (7)
C9	0.0425 (10)	0.0540 (10)	0.0408 (10)	−0.0085 (8)	−0.0032 (8)	−0.0230 (8)
C10	0.0508 (11)	0.0483 (10)	0.0347 (9)	−0.0076 (8)	−0.0026 (8)	−0.0188 (8)
C11	0.0453 (10)	0.0322 (8)	0.0391 (9)	−0.0062 (7)	0.0016 (7)	−0.0160 (7)
C12	0.0423 (10)	0.0523 (10)	0.0444 (10)	−0.0092 (8)	−0.0041 (8)	−0.0219 (9)
C13	0.0512 (11)	0.0480 (10)	0.0355 (9)	−0.0090 (8)	−0.0030 (8)	−0.0188 (8)
C14	0.0457 (10)	0.0462 (10)	0.0515 (11)	−0.0141 (8)	0.0055 (8)	−0.0194 (9)
C15	0.0353 (9)	0.0447 (9)	0.0424 (9)	−0.0120 (7)	0.0045 (7)	−0.0198 (8)
C16	0.0479 (11)	0.0540 (11)	0.0457 (10)	−0.0101 (8)	−0.0079 (8)	−0.0214 (9)
C17	0.0483 (11)	0.0552 (11)	0.0573 (12)	−0.0160 (9)	0.0002 (9)	−0.0321 (10)
C18	0.0379 (9)	0.0427 (9)	0.0550 (11)	−0.0123 (7)	0.0062 (8)	−0.0179 (9)
C19	0.0544 (11)	0.0524 (11)	0.0444 (10)	−0.0118 (9)	0.0011 (8)	−0.0254 (9)
Cl1	0.0732 (4)	0.0415 (3)	0.0948 (5)	−0.0080 (2)	0.0032 (3)	−0.0186 (3)
F1	0.1111 (11)	0.0569 (7)	0.0632 (8)	−0.0301 (7)	0.0031 (7)	−0.0322 (6)
F2	0.1807 (18)	0.0716 (9)	0.0786 (10)	−0.0650 (11)	0.0283 (10)	−0.0444 (8)
N1	0.0453 (9)	0.0451 (8)	0.0327 (8)	−0.0082 (6)	−0.0008 (6)	−0.0161 (7)
N2	0.0541 (10)	0.0527 (9)	0.0428 (9)	−0.0079 (7)	−0.0019 (7)	−0.0173 (7)
O1	0.0500 (8)	0.1190 (14)	0.0444 (8)	−0.0210 (9)	−0.0008 (7)	−0.0348 (9)
O2	0.0436 (7)	0.0507 (7)	0.0411 (7)	−0.0063 (6)	0.0034 (5)	−0.0170 (6)

Geometric parameters (Å, º) top

C1—C6	1.374 (3)	C11—O2	1.377 (2)
C1—C2	1.382 (2)	C11—C12	1.383 (2)
C1—C7	1.504 (2)	C12—C13	1.384 (2)
C2—F1	1.344 (2)	C12—H12	0.9300
C2—C3	1.361 (3)	C13—H13	0.9300
C3—C4	1.366 (3)	C14—O2	1.432 (2)
C3—H3	0.9300	C14—C15	1.508 (2)
C4—C5	1.368 (4)	C14—H14A	0.9700
C4—H4	0.9300	C14—H14B	0.9700
C5—C6	1.374 (3)	C15—C19	1.371 (3)
C5—H5	0.9300	C15—C16	1.391 (2)
C6—F2	1.347 (2)	C16—C17	1.368 (3)
C7—O1	1.217 (2)	C16—H16	0.9300
C7—N1	1.336 (2)	C17—C18	1.372 (3)
C8—C13	1.381 (3)	C17—H17	0.9300
C8—C9	1.390 (2)	C18—N2	1.316 (2)
C8—N1	1.423 (2)	C18—Cl1	1.7328 (19)
C9—C10	1.379 (2)	C19—N2	1.345 (2)
C9—H9	0.9300	C19—H19	0.9300
C10—C11	1.378 (3)	N1—H1	0.88 (2)
C10—H10	0.9300

C6—C1—C2	115.21 (17)	C11—C12—C13	119.36 (17)
C6—C1—C7	121.35 (16)	C11—C12—H12	120.3
C2—C1—C7	122.93 (16)	C13—C12—H12	120.3
F1—C2—C3	119.06 (18)	C8—C13—C12	121.47 (16)
F1—C2—C1	117.06 (16)	C8—C13—H13	119.3
C3—C2—C1	123.86 (19)	C12—C13—H13	119.3
C2—C3—C4	118.0 (2)	O2—C14—C15	111.33 (15)
C2—C3—H3	121.0	O2—C14—H14A	109.4
C4—C3—H3	121.0	C15—C14—H14A	109.4
C3—C4—C5	121.5 (2)	O2—C14—H14B	109.4
C3—C4—H4	119.3	C15—C14—H14B	109.4
C5—C4—H4	119.3	H14A—C14—H14B	108.0
C4—C5—C6	118.1 (2)	C19—C15—C16	116.97 (17)
C4—C5—H5	121.0	C19—C15—C14	122.83 (17)
C6—C5—H5	121.0	C16—C15—C14	120.19 (16)
F2—C6—C1	116.98 (18)	C17—C16—C15	119.99 (17)
F2—C6—C5	119.7 (2)	C17—C16—H16	120.0
C1—C6—C5	123.4 (2)	C15—C16—H16	120.0
O1—C7—N1	125.21 (17)	C16—C17—C18	117.59 (17)
O1—C7—C1	118.93 (16)	C16—C17—H17	121.2
N1—C7—C1	115.86 (15)	C18—C17—H17	121.2
C13—C8—C9	118.73 (16)	N2—C18—C17	124.97 (17)
C13—C8—N1	117.80 (15)	N2—C18—Cl1	116.22 (15)
C9—C8—N1	123.47 (16)	C17—C18—Cl1	118.81 (15)
C10—C9—C8	119.84 (17)	N2—C19—C15	124.31 (17)
C10—C9—H9	120.1	N2—C19—H19	117.8
C8—C9—H9	120.1	C15—C19—H19	117.8
C11—C10—C9	121.11 (16)	C7—N1—C8	127.66 (15)
C11—C10—H10	119.4	C7—N1—H1	116.4 (13)
C9—C10—H10	119.4	C8—N1—H1	115.9 (13)
O2—C11—C10	115.23 (15)	C18—N2—C19	116.17 (17)
O2—C11—C12	125.25 (16)	C11—O2—C14	118.83 (14)
C10—C11—C12	119.49 (16)

C6—C1—C2—F1	178.43 (17)	C10—C11—C12—C13	0.3 (3)
C7—C1—C2—F1	6.5 (3)	C9—C8—C13—C12	0.6 (3)
C6—C1—C2—C3	0.0 (3)	N1—C8—C13—C12	−179.67 (16)
C7—C1—C2—C3	−171.90 (18)	C11—C12—C13—C8	−0.6 (3)
F1—C2—C3—C4	−178.15 (19)	O2—C14—C15—C19	123.96 (19)
C1—C2—C3—C4	0.2 (3)	O2—C14—C15—C16	−56.7 (2)
C2—C3—C4—C5	−0.4 (3)	C19—C15—C16—C17	−0.8 (3)
C3—C4—C5—C6	0.3 (4)	C14—C15—C16—C17	179.80 (17)
C2—C1—C6—F2	−179.11 (18)	C15—C16—C17—C18	0.3 (3)
C7—C1—C6—F2	−7.1 (3)	C16—C17—C18—N2	0.6 (3)
C2—C1—C6—C5	−0.1 (3)	C16—C17—C18—Cl1	179.99 (14)
C7—C1—C6—C5	171.9 (2)	C16—C15—C19—N2	0.7 (3)
C4—C5—C6—F2	178.9 (2)	C14—C15—C19—N2	−179.97 (17)
C4—C5—C6—C1	0.0 (4)	O1—C7—N1—C8	−1.5 (3)
C6—C1—C7—O1	−77.8 (3)	C1—C7—N1—C8	178.76 (15)
C2—C1—C7—O1	93.7 (2)	C13—C8—N1—C7	−170.21 (16)
C6—C1—C7—N1	102.0 (2)	C9—C8—N1—C7	9.5 (3)
C2—C1—C7—N1	−86.6 (2)	C17—C18—N2—C19	−0.7 (3)
C13—C8—C9—C10	−0.3 (3)	Cl1—C18—N2—C19	179.84 (14)
N1—C8—C9—C10	−179.98 (16)	C15—C19—N2—C18	0.1 (3)
C8—C9—C10—C11	0.0 (3)	C10—C11—O2—C14	172.31 (14)
C9—C10—C11—O2	178.18 (16)	C12—C11—O2—C14	−9.6 (2)
C9—C10—C11—C12	0.0 (3)	C15—C14—O2—C11	−78.49 (19)
O2—C11—C12—C13	−177.66 (16)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.93	2.27	2.863 (2)	121
N1—H1···N2ⁱ	0.88 (2)	2.24 (2)	3.109 (2)	170.6 (18)
C19—H19···F2ⁱⁱ	0.93	2.54	3.309 (2)	140
C14—H14B···O1ⁱⁱ	0.97	2.42	3.344 (3)	160
C16—H16···Cg2ⁱⁱⁱ	0.93	2.99	3.912 (2)	173

Symmetry codes: (i) −x, −y+1, −z; (ii) x−1, y, z; (iii) x−1, y, z+1.

Acknowledgements

We gratefully acknowledge the financial support of this work by the Youth Science Foundation of Hubei Academy of Agricultural Sciences (grant No. 2013NKYJJ22) and the Key Laboratory of Integrated Pest Management in Crops in Central China, the Ministry of Agriculture and Hubei Key Laboratory of Crop Diseases, Insect Pests and Weed Control (grant No. 2015ZTSJJ9).

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