N,N′-Bis[4-(trifluoro­meth­yl)phen­yl]pyridine-2,6-dicarboxamide

Chen, L.; He, H.; Peng, H.

doi:10.1107/S1600536810001753

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o405

https://doi.org/10.1107/S1600536810001753

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N,N′-Bis[4-(trifluoromethyl)phenyl]pyridine-2,6-dicarboxamide

Le Chen,^a Hongwu He ^a and Hao Peng ^a ^*

^aKey Laboratory of Pesticide and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.
^*Correspondence e-mail: penghao@mail.ccnu.edu.cn

(Received 28 November 2009; accepted 14 January 2010; online 20 January 2010)

In the title molecule, C₂₁H₁₃F₆N₃O₂, the pyridine ring forms dihedral angles of 1.7 (1) and 5.2 (1)° with the two benzene rings. In the crystal structure, intermolecular N—H⋯O hydrogen bonds and π⋯π interactions [centroid–centroid distance of 3.628 (3) Å between aromatic rings] link molecules into stacks along the c axis. The two trifluoromethyl groups are each rotationally disordered between two orientations, with occupancy ratios of 0.58 (1):0.42 (1) and 0.55 (1):0.45 (1).

Related literature

For the synthesis and biological activity of acyl thiourea derivatives, see: Duan et al. (2003 ); Li et al. (2007 ).

Experimental

Crystal data

C₂₁H₁₃F₆N₃O₂
M_r = 453.34
Monoclinic, P 2₁ /c
a = 9.8308 (10) Å
b = 23.787 (3) Å
c = 8.9577 (10) Å
β = 109.474 (2)°
V = 1974.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 298 K
0.20 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
12033 measured reflections
3653 independent reflections
3138 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.181
S = 1.17
3653 reflections
351 parameters
96 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.84 (3)	2.58 (3)	3.303 (4)	144 (3)
N3—H3A⋯O2ⁱⁱ	0.85 (4)	2.36 (4)	3.051 (3)	139 (3)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810001753/cv2671sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810001753/cv2671Isup2.hkl

checkCIF report

Comment top

Acyl thiourea derivatives have attracted considerable attention from chemists and biologists because of their wide range of biological activities and potential therapeutic value (Duan et al., 2003; Li et al., 2007). In our research work aimed at searching for novel agrochemicals, we attempted to synthesize the pyridine-2,6-dicarbonyl thiourea derivatives,and the title compound, (I), was obtained as byproduct. Here we report its crystal structure.

In (I) (Fig.1), the central pyridine ring makes the dihedral angles of 1.7 (1) and 5.2 (1)° with the two benzene rings, respectively. In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) and π–π interactions proved by short distance of 3.628 (3) Å between the centroids of aromatic rings link molecules into stacks along axis c.

Related literature top

For the synthesis and biological activity of acyl thiourea derivatives, see: Duan et al. (2003); Li et al. (2007).

Experimental top

Pyridine-2,6-dicarbonyl chloride (II) was prepared according to the literature procedures (Duan et al., 2003). To a solution of (II) (5 mmol) in dichloromethane (30 ml) was added KSCN (15 mmol) and PEG-400 (0.2 g). The mixture was stirred at room temperature for 2 h, then 4-trifluoroaniline (10 mmol) was added and the suspension was stirred for 1 h. The mixture was filtered and the precipitate was washed with a little ethanol. The solvent was removed under reduced pressure and the residue was purified by recrystallization from DMF and water (20:1,v/v). Then recrystallization from actone over a period of one week gave colourless crystals of (I).

Structure description top

For the synthesis and biological activity of acyl thiourea derivatives, see: Duan et al. (2003); Li et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of (I), showing the labeling scheme with 50% probability displacement ellipsoids. Only major parts of disordered fluorine atoms are shown.
	Fig. 2. Part of the crystal packing, showing the intermolecular hydrogen bonds as dashed lines.

N,N'-Bis[4-(trifluoromethyl)phenyl]pyridine-2,6-dicarboxamide top

Crystal data top

C₂₁H₁₃F₆N₃O₂	F(000) = 920
M_r = 453.34	D_x = 1.525 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3607 reflections
a = 9.8308 (10) Å	θ = 2.4–25.0°
b = 23.787 (3) Å	µ = 0.14 mm⁻¹
c = 8.9577 (10) Å	T = 298 K
β = 109.474 (2)°	Block, colourless
V = 1974.8 (4) Å³	0.20 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3138 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Graphite monochromator	θ_max = 25.5°, θ_min = 2.2°
phi and ω scans	h = −11→11
12033 measured reflections	k = −28→22
3653 independent reflections	l = −10→10

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ²(F_o²) + (0.0634P)² + 1.4024P] where P = (F_o² + 2F_c²)/3
3653 reflections	(Δ/σ)_max = 0.001
351 parameters	Δρ_max = 0.32 e Å⁻³
96 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₁H₁₃F₆N₃O₂	V = 1974.8 (4) Å³
M_r = 453.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8308 (10) Å	µ = 0.14 mm⁻¹
b = 23.787 (3) Å	T = 298 K
c = 8.9577 (10) Å	0.20 × 0.12 × 0.10 mm
β = 109.474 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3138 reflections with I > 2σ(I)
12033 measured reflections	R_int = 0.043
3653 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	96 restraints
wR(F²) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	Δρ_max = 0.32 e Å⁻³
3653 reflections	Δρ_min = −0.25 e Å⁻³
351 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	Occ. (<1)
C1	0.1924 (3)	0.17950 (12)	0.0978 (3)	0.0384 (7)
C2	0.1982 (4)	0.12169 (14)	0.1004 (4)	0.0491 (8)
H2	0.1447	0.1009	0.1492	0.059*
C3	0.2849 (4)	0.09535 (14)	0.0289 (4)	0.0557 (9)
H3	0.2902	0.0563	0.0282	0.067*
C4	0.3637 (3)	0.12687 (13)	−0.0413 (4)	0.0461 (8)
H4	0.4218	0.1097	−0.0914	0.055*
C5	0.3546 (3)	0.18462 (12)	−0.0356 (3)	0.0356 (6)
C6	0.0990 (3)	0.21071 (13)	0.1728 (3)	0.0400 (7)
C7	−0.0025 (3)	0.30625 (13)	0.1730 (3)	0.0394 (7)
C8	−0.1031 (3)	0.29432 (15)	0.2475 (4)	0.0498 (8)
H8	−0.1244	0.2573	0.2643	0.060*
C9	−0.1704 (3)	0.33774 (17)	0.2959 (4)	0.0581 (9)
H9	−0.2373	0.3298	0.3458	0.070*
C10	−0.1409 (3)	0.39243 (16)	0.2721 (4)	0.0565 (9)
C11	−0.0435 (4)	0.40445 (15)	0.1948 (5)	0.0620 (10)
H11	−0.0236	0.4416	0.1772	0.074*
C12	0.0234 (4)	0.36158 (14)	0.1444 (4)	0.0535 (9)
H12	0.0869	0.3698	0.0904	0.064*
C13	−0.2060 (4)	0.4394 (2)	0.3348 (5)	0.0853 (14)
C14	0.4430 (3)	0.22150 (13)	−0.1048 (3)	0.0377 (7)
C15	0.5242 (3)	0.32122 (13)	−0.0892 (3)	0.0400 (7)
C16	0.4878 (4)	0.37330 (15)	−0.0475 (4)	0.0564 (9)
H16	0.4215	0.3760	0.0057	0.068*
C17	0.5477 (4)	0.42116 (16)	−0.0833 (5)	0.0661 (10)
H17	0.5200	0.4561	−0.0567	0.079*
C18	0.6488 (4)	0.41772 (16)	−0.1585 (4)	0.0599 (10)
C19	0.6873 (4)	0.36594 (17)	−0.1989 (4)	0.0620 (10)
H19	0.7560	0.3635	−0.2492	0.074*
C20	0.6258 (3)	0.31734 (15)	−0.1662 (4)	0.0491 (8)
H20	0.6518	0.2825	−0.1952	0.059*
C21	0.7100 (6)	0.4701 (2)	−0.2000 (5)	0.0930 (16)
N1	0.2702 (2)	0.21094 (10)	0.0320 (3)	0.0357 (6)
N2	0.0727 (3)	0.26423 (11)	0.1232 (3)	0.0430 (6)
H2A	0.110 (4)	0.2753 (14)	0.057 (4)	0.052*
N3	0.4573 (3)	0.27437 (11)	−0.0487 (3)	0.0442 (7)
H3A	0.420 (4)	0.2803 (14)	0.022 (4)	0.053*
O1	0.0553 (3)	0.18852 (10)	0.2706 (3)	0.0663 (7)
O2	0.4942 (3)	0.20366 (10)	−0.2017 (3)	0.0566 (7)
F1	−0.3471 (7)	0.4321 (5)	0.3055 (10)	0.104 (3)	0.55 (1)
F2	−0.1415 (10)	0.4449 (5)	0.4902 (8)	0.130 (4)	0.55 (1)
F3	−0.1944 (10)	0.4899 (3)	0.2690 (12)	0.127 (4)	0.55 (1)
F4	0.7508 (11)	0.5071 (4)	−0.0789 (9)	0.143 (4)	0.58 (1)
F5	0.6273 (14)	0.4946 (5)	−0.3320 (9)	0.122 (4)	0.58 (1)
F6	0.8385 (8)	0.4579 (5)	−0.2243 (14)	0.133 (4)	0.58 (1)
F4'	0.8527 (8)	0.4711 (6)	−0.1667 (18)	0.119 (5)	0.45 (1)
F1'	−0.3145 (10)	0.4220 (6)	0.3872 (14)	0.130 (5)	0.45 (1)
F5'	0.6697 (11)	0.5178 (4)	−0.1386 (12)	0.109 (3)	0.45 (1)
F3'	−0.1123 (11)	0.4662 (5)	0.4586 (11)	0.088 (3)	0.42 (1)
F2'	−0.2616 (11)	0.4801 (5)	0.2255 (12)	0.110 (4)	0.42 (1)
F6'	0.6506 (17)	0.4783 (6)	−0.3602 (9)	0.102 (4)	0.42 (1)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0394 (16)	0.0387 (17)	0.0408 (16)	−0.0035 (12)	0.0182 (13)	−0.0019 (13)
C2	0.0565 (19)	0.0434 (19)	0.0562 (19)	−0.0060 (15)	0.0305 (16)	−0.0004 (15)
C3	0.073 (2)	0.0319 (17)	0.072 (2)	0.0011 (15)	0.038 (2)	−0.0021 (16)
C4	0.0534 (18)	0.0430 (18)	0.0489 (18)	0.0050 (14)	0.0265 (15)	−0.0026 (14)
C5	0.0329 (14)	0.0392 (16)	0.0366 (15)	0.0050 (12)	0.0141 (12)	0.0006 (12)
C6	0.0395 (16)	0.0422 (18)	0.0456 (17)	−0.0055 (13)	0.0240 (14)	−0.0025 (13)
C7	0.0328 (15)	0.0467 (18)	0.0411 (16)	0.0030 (13)	0.0156 (13)	−0.0040 (13)
C8	0.0390 (17)	0.055 (2)	0.063 (2)	0.0000 (15)	0.0275 (16)	−0.0046 (16)
C9	0.0402 (18)	0.079 (3)	0.065 (2)	0.0021 (17)	0.0302 (17)	−0.0110 (19)
C10	0.0404 (18)	0.064 (2)	0.066 (2)	0.0063 (16)	0.0181 (16)	−0.0184 (18)
C11	0.053 (2)	0.048 (2)	0.089 (3)	0.0048 (16)	0.029 (2)	−0.0085 (19)
C12	0.0492 (19)	0.050 (2)	0.071 (2)	0.0047 (15)	0.0340 (17)	0.0023 (17)
C13	0.063 (3)	0.097 (4)	0.100 (4)	0.010 (3)	0.033 (3)	−0.036 (3)
C14	0.0383 (15)	0.0421 (17)	0.0366 (15)	0.0093 (12)	0.0176 (13)	0.0027 (13)
C15	0.0410 (16)	0.0450 (18)	0.0356 (15)	−0.0033 (13)	0.0148 (13)	0.0016 (13)
C16	0.065 (2)	0.052 (2)	0.064 (2)	−0.0091 (17)	0.0378 (19)	−0.0066 (17)
C17	0.084 (3)	0.047 (2)	0.076 (3)	−0.0112 (19)	0.039 (2)	−0.0073 (18)
C18	0.069 (2)	0.060 (2)	0.051 (2)	−0.0187 (18)	0.0202 (18)	0.0026 (17)
C19	0.062 (2)	0.077 (3)	0.059 (2)	−0.0150 (19)	0.0363 (19)	0.0027 (19)
C20	0.0469 (18)	0.054 (2)	0.0533 (19)	−0.0017 (15)	0.0264 (16)	0.0008 (16)
C21	0.127 (5)	0.078 (4)	0.087 (4)	−0.039 (3)	0.053 (4)	0.003 (3)
N1	0.0353 (12)	0.0357 (13)	0.0395 (13)	0.0021 (10)	0.0172 (10)	0.0003 (10)
N2	0.0471 (15)	0.0428 (16)	0.0516 (15)	0.0024 (11)	0.0330 (13)	0.0022 (12)
N3	0.0548 (16)	0.0436 (15)	0.0489 (15)	−0.0040 (12)	0.0371 (13)	−0.0027 (12)
O1	0.0879 (18)	0.0535 (15)	0.0839 (18)	0.0034 (13)	0.0640 (16)	0.0105 (13)
O2	0.0733 (16)	0.0520 (14)	0.0635 (15)	0.0044 (12)	0.0482 (13)	−0.0026 (11)
F1	0.063 (4)	0.126 (6)	0.131 (6)	0.029 (4)	0.044 (4)	−0.042 (5)
F2	0.124 (7)	0.159 (10)	0.107 (5)	0.023 (5)	0.040 (5)	−0.073 (5)
F3	0.128 (8)	0.071 (4)	0.203 (11)	0.015 (5)	0.084 (7)	−0.041 (6)
F4	0.209 (10)	0.102 (6)	0.134 (6)	−0.089 (6)	0.078 (7)	−0.024 (5)
F5	0.175 (7)	0.070 (7)	0.137 (7)	−0.004 (4)	0.072 (6)	0.036 (5)
F6	0.147 (7)	0.129 (8)	0.147 (8)	−0.095 (5)	0.081 (5)	−0.024 (5)
F4'	0.115 (7)	0.088 (7)	0.157 (11)	−0.060 (5)	0.049 (6)	−0.004 (7)
F1'	0.091 (7)	0.134 (9)	0.197 (12)	−0.011 (6)	0.092 (7)	−0.084 (9)
F5'	0.168 (9)	0.055 (4)	0.127 (7)	−0.043 (5)	0.082 (7)	−0.019 (5)
F3'	0.071 (4)	0.078 (6)	0.111 (7)	0.003 (4)	0.024 (5)	−0.050 (4)
F2'	0.097 (8)	0.094 (8)	0.118 (6)	0.052 (6)	0.007 (6)	−0.025 (6)
F6'	0.171 (10)	0.067 (8)	0.090 (6)	−0.008 (5)	0.075 (6)	0.022 (4)

Geometric parameters (Å, º) top

C1—N1	1.339 (4)	C13—F3'	1.342 (8)
C1—C2	1.376 (4)	C13—F2'	1.355 (8)
C1—C6	1.502 (4)	C13—F3	1.358 (7)
C2—C3	1.376 (4)	C13—F1'	1.365 (8)
C2—H2	0.9300	C14—O2	1.216 (3)
C3—C4	1.372 (4)	C14—N3	1.344 (4)
C3—H3	0.9300	C15—C16	1.375 (5)
C4—C5	1.379 (4)	C15—C20	1.393 (4)
C4—H4	0.9300	C15—N3	1.402 (4)
C5—N1	1.335 (3)	C16—C17	1.368 (5)
C5—C14	1.506 (4)	C16—H16	0.9300
C6—O1	1.217 (3)	C17—C18	1.377 (5)
C6—N2	1.345 (4)	C17—H17	0.9300
C7—C12	1.381 (5)	C18—C19	1.372 (5)
C7—C8	1.394 (4)	C18—C21	1.484 (5)
C7—N2	1.402 (4)	C19—C20	1.380 (5)
C8—C9	1.373 (5)	C19—H19	0.9300
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.365 (5)	C21—F5	1.326 (8)
C9—H9	0.9300	C21—F4'	1.334 (8)
C10—C11	1.386 (5)	C21—F4	1.350 (7)
C10—C13	1.488 (5)	C21—F6'	1.371 (8)
C11—C12	1.369 (5)	C21—F5'	1.375 (8)
C11—H11	0.9300	C21—F6	1.383 (8)
C12—H12	0.9300	N2—H2A	0.84 (3)
C13—F2	1.330 (7)	N3—H3A	0.85 (4)
C13—F1	1.335 (7)

N1—C1—C2	122.6 (3)	F3'—C13—C10	113.9 (6)
N1—C1—C6	116.4 (2)	F2'—C13—C10	112.7 (7)
C2—C1—C6	120.9 (3)	F3—C13—C10	113.1 (6)
C1—C2—C3	118.4 (3)	F1'—C13—C10	112.7 (7)
C1—C2—H2	120.8	O2—C14—N3	125.2 (3)
C3—C2—H2	120.8	O2—C14—C5	121.6 (3)
C4—C3—C2	119.8 (3)	N3—C14—C5	113.2 (2)
C4—C3—H3	120.1	C16—C15—C20	119.2 (3)
C2—C3—H3	120.1	C16—C15—N3	117.3 (3)
C3—C4—C5	118.3 (3)	C20—C15—N3	123.5 (3)
C3—C4—H4	120.8	C17—C16—C15	121.0 (3)
C5—C4—H4	120.8	C17—C16—H16	119.5
N1—C5—C4	122.8 (3)	C15—C16—H16	119.5
N1—C5—C14	116.4 (2)	C16—C17—C18	120.2 (4)
C4—C5—C14	120.8 (3)	C16—C17—H17	119.9
O1—C6—N2	125.0 (3)	C18—C17—H17	119.9
O1—C6—C1	121.5 (3)	C19—C18—C17	119.3 (3)
N2—C6—C1	113.5 (2)	C19—C18—C21	121.2 (4)
C12—C7—C8	119.1 (3)	C17—C18—C21	119.4 (4)
C12—C7—N2	118.1 (3)	C18—C19—C20	121.1 (3)
C8—C7—N2	122.7 (3)	C18—C19—H19	119.4
C9—C8—C7	119.5 (3)	C20—C19—H19	119.4
C9—C8—H8	120.3	C19—C20—C15	119.1 (3)
C7—C8—H8	120.3	C19—C20—H20	120.4
C10—C9—C8	121.2 (3)	C15—C20—H20	120.4
C10—C9—H9	119.4	F5—C21—F4'	118.5 (12)
C8—C9—H9	119.4	F5—C21—F4	111.1 (7)
C9—C10—C11	119.6 (3)	F4'—C21—F4	78.5 (7)
C9—C10—C13	121.1 (3)	F5—C21—F6'	23.6 (8)
C11—C10—C13	119.3 (4)	F4'—C21—F6'	106.3 (8)
C12—C11—C10	119.9 (3)	F4—C21—F6'	131.1 (9)
C12—C11—H11	120.0	F5—C21—F5'	79.7 (7)
C10—C11—H11	120.0	F4'—C21—F5'	108.5 (7)
C11—C12—C7	120.7 (3)	F4—C21—F5'	35.8 (6)
C11—C12—H12	119.7	F6'—C21—F5'	102.9 (7)
C7—C12—H12	119.7	F5—C21—F6	105.8 (7)
F2—C13—F1	108.7 (6)	F4'—C21—F6	24.6 (7)
F2—C13—F3'	29.8 (7)	F4—C21—F6	102.8 (6)
F1—C13—F3'	127.3 (8)	F6'—C21—F6	87.6 (10)
F2—C13—F2'	128.5 (8)	F5'—C21—F6	129.5 (7)
F1—C13—F2'	79.0 (7)	F5—C21—C18	114.4 (8)
F3'—C13—F2'	105.0 (7)	F4'—C21—C18	116.3 (8)
F2—C13—F3	106.7 (6)	F4—C21—C18	112.5 (6)
F1—C13—F3	105.2 (6)	F6'—C21—C18	108.3 (8)
F3'—C13—F3	78.8 (7)	F5'—C21—C18	113.5 (6)
F2'—C13—F3	29.3 (5)	F6—C21—C18	109.3 (6)
F2—C13—F1'	79.9 (7)	C5—N1—C1	118.1 (2)
F1—C13—F1'	31.5 (6)	C6—N2—C7	129.3 (3)
F3'—C13—F1'	105.0 (7)	C6—N2—H2A	117 (2)
F2'—C13—F1'	106.9 (7)	C7—N2—H2A	114 (2)
F3—C13—F1'	127.2 (8)	C14—N3—C15	130.2 (3)
F2—C13—C10	110.7 (6)	C14—N3—H3A	115 (2)
F1—C13—C10	112.1 (6)	C15—N3—H3A	115 (2)

N1—C1—C2—C3	−1.6 (5)	C4—C5—C14—N3	−160.5 (3)
C6—C1—C2—C3	179.6 (3)	C20—C15—C16—C17	1.3 (5)
C1—C2—C3—C4	0.5 (5)	N3—C15—C16—C17	−179.7 (3)
C2—C3—C4—C5	0.9 (5)	C15—C16—C17—C18	−1.7 (6)
C3—C4—C5—N1	−1.5 (5)	C16—C17—C18—C19	0.9 (6)
C3—C4—C5—C14	177.6 (3)	C16—C17—C18—C21	178.5 (4)
N1—C1—C6—O1	−159.9 (3)	C17—C18—C19—C20	0.3 (6)
C2—C1—C6—O1	19.0 (5)	C21—C18—C19—C20	−177.2 (4)
N1—C1—C6—N2	18.9 (4)	C18—C19—C20—C15	−0.7 (5)
C2—C1—C6—N2	−162.2 (3)	C16—C15—C20—C19	0.0 (5)
C12—C7—C8—C9	−2.3 (5)	N3—C15—C20—C19	−179.0 (3)
N2—C7—C8—C9	178.7 (3)	C19—C18—C21—F5	96.4 (7)
C7—C8—C9—C10	0.1 (5)	C17—C18—C21—F5	−81.2 (7)
C8—C9—C10—C11	1.3 (5)	C19—C18—C21—F4'	−47.7 (8)
C8—C9—C10—C13	−175.6 (3)	C17—C18—C21—F4'	134.7 (8)
C9—C10—C11—C12	−0.6 (5)	C19—C18—C21—F4	−135.6 (6)
C13—C10—C11—C12	176.3 (4)	C17—C18—C21—F4	46.8 (7)
C10—C11—C12—C7	−1.5 (5)	C19—C18—C21—F6'	71.8 (8)
C8—C7—C12—C11	3.0 (5)	C17—C18—C21—F6'	−105.7 (7)
N2—C7—C12—C11	−178.0 (3)	C19—C18—C21—F5'	−174.6 (6)
C9—C10—C13—F2	75.5 (6)	C17—C18—C21—F5'	7.8 (7)
C11—C10—C13—F2	−101.4 (6)	C19—C18—C21—F6	−22.1 (7)
C9—C10—C13—F1	−46.1 (7)	C17—C18—C21—F6	160.3 (6)
C11—C10—C13—F1	137.0 (6)	C4—C5—N1—C1	0.6 (4)
C9—C10—C13—F3'	107.6 (7)	C14—C5—N1—C1	−178.6 (2)
C11—C10—C13—F3'	−69.4 (7)	C2—C1—N1—C5	1.0 (4)
C9—C10—C13—F2'	−133.0 (6)	C6—C1—N1—C5	179.9 (2)
C11—C10—C13—F2'	50.1 (7)	O1—C6—N2—C7	2.6 (5)
C9—C10—C13—F3	−164.8 (6)	C1—C6—N2—C7	−176.2 (3)
C11—C10—C13—F3	18.2 (7)	C12—C7—N2—C6	159.3 (3)
C9—C10—C13—F1'	−11.9 (7)	C8—C7—N2—C6	−21.7 (5)
C11—C10—C13—F1'	171.2 (6)	O2—C14—N3—C15	3.4 (5)
N1—C5—C14—O2	−161.2 (3)	C5—C14—N3—C15	−176.4 (3)
C4—C5—C14—O2	19.7 (4)	C16—C15—N3—C14	161.7 (3)
N1—C5—C14—N3	18.6 (4)	C20—C15—N3—C14	−19.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.84 (3)	2.58 (3)	3.303 (4)	144 (3)
N3—H3A···O2ⁱⁱ	0.85 (4)	2.36 (4)	3.051 (3)	139 (3)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₃F₆N₃O₂
M_r	453.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.8308 (10), 23.787 (3), 8.9577 (10)
β (°)	109.474 (2)
V (Å³)	1974.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.20 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12033, 3653, 3138
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.181, 1.17
No. of reflections	3653
No. of parameters	351
No. of restraints	96
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.25

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.84 (3)	2.58 (3)	3.303 (4)	144 (3)
N3—H3A···O2ⁱⁱ	0.85 (4)	2.36 (4)	3.051 (3)	139 (3)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2.

Acknowledgements

We gratefully acknowledge the financial support of this work by the Opening Foundation of the Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University (grant No. 2009GDGP0101), the National Basic Research Program of China (2010CB126100) and the National Natural Science Foundation of China (No. 20772042).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Duan, Z. F., Gu, L. Q., Huang, Z. S., Xie, W. L. & Ma, L. (2003). Chin. J. Appl. Chem. 20, 80–82. CAS Google Scholar
Li, Y. J., Zhang, Z. G., Jin, K., Peng, Q. J., Ding, W. G. & Liu, J. (2007). Acta Chim. Sin. 65, 834–840. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar