N-[4-Chloro-2-methyl-6-(N-methyl-car-bam-oyl)phen-yl]-1-(3-chloro-2-pyrid-yl)-3-trifluoro-meth-yl-1H-pyrazole-5-carboxamide.

In the title compound, C(19)H(14)Cl(2)F(3)N(5)O(2), which shows insecticidal activity, the dihedral angle between the pyrazole and pyridine rings is 68.15 (16)°. In the crystal structure, the mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds and an intra-molecular N-H⋯O inter-action also occurs. The F atoms of the -CF(3) group are disordered over two sets of sites in a 0.800 (8):0.200 (8) ratio.

Related literature

For the synthesis and background to the insecticidal properties of the title compound, see: Lahm et al. (2003 ▶, 2005 ▶).

Experimental

Crystal data

C19H14Cl2F3N5O2

M = 472.25

Orthorhombic,

a = 26.4612 (16) Å

b = 32.8657 (19) Å

c = 9.4679 (6) Å

V = 8233.9 (9) Å3

Z = 16

Mo Kα radiation

μ = 0.37 mm−1

T = 296 (2) K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.917, T max = 0.937

10439 measured reflections

3565 independent reflections

3284 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.082

S = 1.04

3565 reflections

310 parameters

49 restraints

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1621 Friedel pairs

Flack parameter: −0.01 (7)

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808037604/hb2777sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037604/hb2777Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H14Cl2F3N5O2	Dx = 1.524 Mg m−3
Mr = 472.25	Melting point: 492(1) K
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
a = 26.4612 (16) Å	Cell parameters from 3952 reflections
b = 32.8657 (19) Å	θ = 2.4–23.9°
c = 9.4679 (6) Å	µ = 0.37 mm−1
V = 8233.9 (9) Å3	T = 296 K
Z = 16	Block, colourless
F(000) = 3840	0.24 × 0.20 × 0.18 mm

Bruker SMART CCD diffractometer	3565 independent reflections
Radiation source: fine-focus sealed tube	3284 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −31→24
Tmin = 0.917, Tmax = 0.937	k = −34→38
10439 measured reflections	l = −11→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0387P)2 + 8.8659P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3565 reflections	Δρmax = 0.18 e Å−3
310 parameters	Δρmin = −0.20 e Å−3
49 restraints	Absolute structure: Flack (1983), 1621 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (7)

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	Occ. (<1)
Cl1	0.28309 (3)	1.00598 (3)	0.40561 (10)	0.0647 (3)
Cl2	0.46782 (4)	0.85540 (5)	−0.17854 (12)	0.1075 (5)
F1	0.39895 (14)	1.06805 (12)	0.8595 (6)	0.1059 (17)	0.800 (8)
F2	0.4312 (2)	1.01859 (14)	0.9614 (4)	0.1148 (18)	0.800 (8)
F3	0.47071 (12)	1.04708 (16)	0.7981 (5)	0.0958 (15)	0.800 (8)
F1'	0.4028 (5)	1.0381 (5)	0.9535 (11)	0.074 (4)	0.200 (8)
F2'	0.4714 (4)	1.0263 (5)	0.8653 (18)	0.087 (5)	0.200 (8)
F3'	0.4283 (7)	1.0724 (3)	0.7878 (16)	0.106 (6)	0.200 (8)
O1	0.36097 (7)	0.91496 (6)	0.4022 (2)	0.0453 (5)
O2	0.52136 (8)	0.96046 (6)	0.3535 (3)	0.0576 (6)
N1	0.35642 (9)	0.99358 (8)	0.7518 (3)	0.0445 (6)
N2	0.34753 (8)	0.97021 (6)	0.6376 (2)	0.0360 (5)
N3	0.28654 (9)	0.92344 (8)	0.7109 (3)	0.0479 (6)
N4	0.42127 (8)	0.95772 (6)	0.3170 (2)	0.0342 (5)
H4	0.4359	0.9808	0.3291	0.041*
N5	0.56488 (8)	0.90701 (7)	0.2779 (3)	0.0419 (6)
H5	0.5672	0.8873	0.2186	0.050*
C1	0.26575 (11)	0.96695 (9)	0.5174 (3)	0.0448 (7)
C2	0.21856 (11)	0.94974 (11)	0.5056 (4)	0.0566 (9)
H2	0.1958	0.9587	0.4375	0.068*
C3	0.20605 (12)	0.91908 (11)	0.5966 (4)	0.0602 (10)
H3	0.1747	0.9064	0.5899	0.072*
C4	0.23980 (14)	0.90720 (10)	0.6975 (4)	0.0592 (9)
H4A	0.2302	0.8869	0.7604	0.071*
C5	0.29811 (10)	0.95245 (8)	0.6209 (3)	0.0379 (6)
C6	0.40279 (10)	1.00776 (9)	0.7321 (3)	0.0434 (7)
C7	0.42585 (12)	1.03518 (11)	0.8368 (4)	0.0596 (9)
C8	0.42392 (10)	0.99401 (9)	0.6056 (3)	0.0429 (7)
H8	0.4558	1.0000	0.5695	0.052*
C9	0.38752 (10)	0.96987 (8)	0.5464 (3)	0.0346 (6)
C10	0.38824 (9)	0.94496 (7)	0.4152 (3)	0.0329 (6)
C11	0.43316 (10)	0.93476 (7)	0.1941 (3)	0.0323 (6)
C12	0.48281 (9)	0.92011 (7)	0.1738 (3)	0.0319 (6)
C13	0.49293 (10)	0.89622 (9)	0.0565 (3)	0.0415 (6)
H13	0.5254	0.8864	0.0410	0.050*
C14	0.45484 (12)	0.88718 (10)	−0.0367 (3)	0.0534 (8)
C15	0.40693 (11)	0.90324 (10)	−0.0207 (3)	0.0507 (8)
H15	0.3822	0.8976	−0.0875	0.061*
C16	0.39557 (10)	0.92751 (9)	0.0935 (3)	0.0401 (6)
C17	0.34412 (11)	0.94686 (11)	0.1030 (4)	0.0565 (8)
H17A	0.3290	0.9476	0.0108	0.085*
H17B	0.3474	0.9741	0.1385	0.085*
H17C	0.3232	0.9313	0.1656	0.085*
C18	0.52432 (10)	0.93058 (8)	0.2762 (3)	0.0334 (6)
C19	0.60538 (12)	0.91391 (11)	0.3778 (4)	0.0597 (9)
H19A	0.6216	0.9394	0.3571	0.090*
H19B	0.6296	0.8923	0.3708	0.090*
H19C	0.5918	0.9147	0.4718	0.090*

	U11	U22	U33	U12	U13	U23
Cl1	0.0572 (5)	0.0631 (5)	0.0737 (6)	0.0044 (4)	−0.0053 (4)	0.0203 (5)
Cl2	0.0781 (7)	0.1621 (12)	0.0821 (8)	0.0360 (7)	−0.0273 (6)	−0.0839 (8)
F1	0.090 (2)	0.090 (2)	0.137 (3)	0.0050 (19)	−0.020 (2)	−0.063 (2)
F2	0.168 (4)	0.117 (3)	0.059 (2)	−0.042 (3)	−0.040 (2)	−0.0052 (18)
F3	0.067 (2)	0.132 (3)	0.088 (3)	−0.0499 (19)	0.0139 (17)	−0.043 (2)
F1'	0.067 (6)	0.095 (6)	0.060 (6)	−0.014 (5)	0.009 (4)	−0.021 (5)
F2'	0.072 (6)	0.094 (6)	0.094 (7)	0.004 (5)	−0.017 (5)	−0.018 (5)
F3'	0.121 (8)	0.094 (7)	0.103 (7)	−0.008 (5)	−0.014 (5)	−0.004 (5)
O1	0.0485 (11)	0.0440 (11)	0.0433 (11)	−0.0146 (9)	0.0108 (10)	−0.0005 (9)
O2	0.0434 (12)	0.0537 (12)	0.0757 (17)	0.0105 (10)	−0.0185 (11)	−0.0324 (12)
N1	0.0407 (13)	0.0564 (15)	0.0365 (13)	−0.0054 (11)	0.0038 (10)	−0.0095 (11)
N2	0.0312 (11)	0.0441 (12)	0.0326 (12)	−0.0019 (9)	0.0043 (9)	−0.0051 (10)
N3	0.0511 (15)	0.0500 (14)	0.0426 (14)	−0.0052 (12)	0.0153 (11)	−0.0014 (12)
N4	0.0332 (11)	0.0331 (11)	0.0364 (13)	−0.0044 (9)	0.0052 (10)	−0.0030 (10)
N5	0.0347 (12)	0.0433 (13)	0.0478 (14)	0.0065 (10)	−0.0059 (10)	−0.0128 (11)
C1	0.0378 (16)	0.0472 (16)	0.0492 (18)	0.0027 (13)	0.0053 (13)	−0.0069 (14)
C2	0.0356 (17)	0.067 (2)	0.067 (2)	−0.0003 (15)	−0.0020 (16)	−0.0149 (18)
C3	0.0381 (17)	0.068 (2)	0.075 (2)	−0.0137 (16)	0.0124 (17)	−0.022 (2)
C4	0.065 (2)	0.0553 (19)	0.058 (2)	−0.0176 (17)	0.0271 (17)	−0.0078 (16)
C5	0.0335 (14)	0.0422 (15)	0.0380 (16)	−0.0023 (11)	0.0100 (12)	−0.0074 (12)
C6	0.0380 (16)	0.0545 (17)	0.0376 (16)	−0.0054 (13)	−0.0001 (12)	−0.0042 (13)
C7	0.0503 (19)	0.077 (2)	0.052 (2)	−0.0108 (18)	0.0062 (16)	−0.0155 (18)
C8	0.0326 (14)	0.0557 (17)	0.0405 (16)	−0.0058 (13)	0.0051 (12)	−0.0010 (13)
C9	0.0337 (14)	0.0392 (14)	0.0307 (13)	0.0022 (11)	0.0021 (11)	0.0020 (11)
C10	0.0288 (13)	0.0351 (13)	0.0347 (14)	0.0006 (11)	0.0028 (11)	0.0050 (11)
C11	0.0330 (13)	0.0329 (13)	0.0310 (14)	−0.0043 (11)	0.0016 (11)	0.0042 (10)
C12	0.0314 (13)	0.0310 (12)	0.0333 (14)	−0.0044 (10)	0.0008 (11)	0.0008 (11)
C13	0.0357 (14)	0.0499 (16)	0.0391 (15)	0.0027 (12)	0.0002 (12)	−0.0068 (13)
C14	0.0502 (18)	0.069 (2)	0.0405 (17)	0.0035 (16)	−0.0066 (13)	−0.0218 (16)
C15	0.0422 (17)	0.071 (2)	0.0392 (17)	−0.0054 (15)	−0.0108 (13)	−0.0092 (16)
C16	0.0319 (14)	0.0501 (16)	0.0383 (16)	−0.0040 (12)	0.0012 (11)	0.0034 (13)
C17	0.0365 (15)	0.085 (2)	0.0481 (19)	0.0068 (16)	−0.0051 (14)	0.0040 (16)
C18	0.0335 (14)	0.0308 (13)	0.0359 (15)	−0.0015 (11)	−0.0003 (11)	−0.0020 (11)
C19	0.0393 (17)	0.073 (2)	0.067 (2)	0.0107 (15)	−0.0141 (15)	−0.0186 (19)

Cl1—C1	1.725 (3)	C2—H2	0.9300
Cl2—C14	1.736 (3)	C3—C4	1.365 (5)
F1—C7	1.311 (4)	C3—H3	0.9300
F2—C7	1.307 (4)	C4—H4A	0.9300
F3—C7	1.303 (4)	C6—C8	1.397 (4)
F1'—C7	1.266 (8)	C6—C7	1.472 (4)
F2'—C7	1.269 (8)	C8—C9	1.368 (4)
F3'—C7	1.310 (8)	C8—H8	0.9300
O1—C10	1.228 (3)	C9—C10	1.488 (4)
O2—C18	1.227 (3)	C11—C16	1.397 (4)
N1—C6	1.326 (4)	C11—C12	1.412 (4)
N1—N2	1.347 (3)	C12—C13	1.387 (4)
N2—C9	1.366 (3)	C12—C18	1.505 (3)
N2—C5	1.441 (3)	C13—C14	1.372 (4)
N3—C5	1.315 (4)	C13—H13	0.9300
N3—C4	1.353 (4)	C14—C15	1.382 (4)
N4—C10	1.343 (3)	C15—C16	1.377 (4)
N4—C11	1.423 (3)	C15—H15	0.9300
N4—H4	0.8600	C16—C17	1.505 (4)
N5—C18	1.324 (3)	C17—H17A	0.9600
N5—C19	1.447 (4)	C17—H17B	0.9600
N5—H5	0.8600	C17—H17C	0.9600
C1—C2	1.375 (4)	C19—H19A	0.9600
C1—C5	1.386 (4)	C19—H19B	0.9600
C2—C3	1.367 (5)	C19—H19C	0.9600
C6—N1—N2	104.4 (2)	F3—C7—C6	111.8 (3)
N1—N2—C9	112.1 (2)	F2—C7—C6	113.4 (3)
N1—N2—C5	118.5 (2)	F3'—C7—C6	110.7 (7)
C9—N2—C5	129.1 (2)	F1—C7—C6	112.9 (3)
C5—N3—C4	116.0 (3)	C9—C8—C6	104.9 (2)
C10—N4—C11	123.0 (2)	C9—C8—H8	127.5
C10—N4—H4	118.5	C6—C8—H8	127.5
C11—N4—H4	118.5	N2—C9—C8	106.3 (2)
C18—N5—C19	121.1 (2)	N2—C9—C10	122.9 (2)
C18—N5—H5	119.5	C8—C9—C10	130.7 (2)
C19—N5—H5	119.5	O1—C10—N4	124.3 (2)
C2—C1—C5	118.5 (3)	O1—C10—C9	121.2 (2)
C2—C1—Cl1	119.8 (3)	N4—C10—C9	114.5 (2)
C5—C1—Cl1	121.7 (2)	C16—C11—C12	120.8 (2)
C3—C2—C1	118.1 (3)	C16—C11—N4	119.4 (2)
C3—C2—H2	120.9	C12—C11—N4	119.8 (2)
C1—C2—H2	120.9	C13—C12—C11	118.8 (2)
C4—C3—C2	119.6 (3)	C13—C12—C18	120.3 (2)
C4—C3—H3	120.2	C11—C12—C18	120.9 (2)
C2—C3—H3	120.2	C14—C13—C12	119.7 (3)
N3—C4—C3	123.4 (3)	C14—C13—H13	120.1
N3—C4—H4A	118.3	C12—C13—H13	120.1
C3—C4—H4A	118.3	C13—C14—C15	121.4 (3)
N3—C5—C1	124.3 (3)	C13—C14—Cl2	118.8 (2)
N3—C5—N2	115.7 (3)	C15—C14—Cl2	119.8 (2)
C1—C5—N2	119.9 (2)	C16—C15—C14	120.5 (3)
N1—C6—C8	112.2 (3)	C16—C15—H15	119.7
N1—C6—C7	120.2 (3)	C14—C15—H15	119.7
C8—C6—C7	127.6 (3)	C15—C16—C11	118.6 (3)
F1'—C7—F2'	106.9 (8)	C15—C16—C17	119.3 (3)
F1'—C7—F3	131.5 (6)	C11—C16—C17	122.1 (3)
F2'—C7—F3	42.6 (7)	C16—C17—H17A	109.5
F1'—C7—F2	45.3 (7)	C16—C17—H17B	109.5
F2'—C7—F2	67.0 (8)	H17A—C17—H17B	109.5
F3—C7—F2	106.3 (4)	C16—C17—H17C	109.5
F1'—C7—F3'	105.2 (8)	H17A—C17—H17C	109.5
F2'—C7—F3'	104.1 (8)	H17B—C17—H17C	109.5
F3—C7—F3'	64.8 (8)	O2—C18—N5	120.9 (2)
F2—C7—F3'	134.7 (7)	O2—C18—C12	121.4 (2)
F1'—C7—F1	62.1 (7)	N5—C18—C12	117.7 (2)
F2'—C7—F1	132.1 (7)	N5—C19—H19A	109.5
F3—C7—F1	107.1 (4)	N5—C19—H19B	109.5
F2—C7—F1	104.8 (4)	H19A—C19—H19B	109.5
F3'—C7—F1	46.8 (8)	N5—C19—H19C	109.5
F1'—C7—C6	115.8 (6)	H19A—C19—H19C	109.5
F2'—C7—C6	113.3 (7)	H19B—C19—H19C	109.5
C6—N1—N2—C9	−0.5 (3)	N1—N2—C9—C10	177.2 (2)
C6—N1—N2—C5	−175.3 (2)	C5—N2—C9—C10	−8.7 (4)
C5—C1—C2—C3	−0.1 (4)	C6—C8—C9—N2	−0.2 (3)
Cl1—C1—C2—C3	−179.5 (3)	C6—C8—C9—C10	−176.6 (3)
C1—C2—C3—C4	1.5 (5)	C11—N4—C10—O1	−8.6 (4)
C5—N3—C4—C3	1.0 (4)	C11—N4—C10—C9	170.3 (2)
C2—C3—C4—N3	−2.0 (5)	N2—C9—C10—O1	−22.0 (4)
C4—N3—C5—C1	0.5 (4)	C8—C9—C10—O1	154.0 (3)
C4—N3—C5—N2	178.7 (2)	N2—C9—C10—N4	159.1 (2)
C2—C1—C5—N3	−1.0 (4)	C8—C9—C10—N4	−24.9 (4)
Cl1—C1—C5—N3	178.5 (2)	C10—N4—C11—C16	64.7 (3)
C2—C1—C5—N2	−179.1 (3)	C10—N4—C11—C12	−116.2 (3)
Cl1—C1—C5—N2	0.4 (4)	C16—C11—C12—C13	−3.9 (4)
N1—N2—C5—N3	−69.8 (3)	N4—C11—C12—C13	177.1 (2)
C9—N2—C5—N3	116.4 (3)	C16—C11—C12—C18	175.2 (2)
N1—N2—C5—C1	108.4 (3)	N4—C11—C12—C18	−3.8 (3)
C9—N2—C5—C1	−65.4 (4)	C11—C12—C13—C14	−0.3 (4)
N2—N1—C6—C8	0.4 (3)	C18—C12—C13—C14	−179.4 (3)
N2—N1—C6—C7	179.6 (3)	C12—C13—C14—C15	3.7 (5)
N1—C6—C7—F1'	11.8 (10)	C12—C13—C14—Cl2	−177.2 (2)
C8—C6—C7—F1'	−169.1 (10)	C13—C14—C15—C16	−2.8 (5)
N1—C6—C7—F2'	135.8 (10)	Cl2—C14—C15—C16	178.0 (3)
C8—C6—C7—F2'	−45.1 (11)	C14—C15—C16—C11	−1.4 (4)
N1—C6—C7—F3	−177.9 (4)	C14—C15—C16—C17	175.9 (3)
C8—C6—C7—F3	1.1 (6)	C12—C11—C16—C15	4.7 (4)
N1—C6—C7—F2	61.9 (5)	N4—C11—C16—C15	−176.2 (2)
C8—C6—C7—F2	−119.0 (5)	C12—C11—C16—C17	−172.5 (3)
N1—C6—C7—F3'	−107.7 (10)	N4—C11—C16—C17	6.6 (4)
C8—C6—C7—F3'	71.4 (11)	C19—N5—C18—O2	4.6 (4)
N1—C6—C7—F1	−57.1 (5)	C19—N5—C18—C12	−177.1 (3)
C8—C6—C7—F1	122.0 (4)	C13—C12—C18—O2	157.4 (3)
N1—C6—C8—C9	−0.2 (3)	C11—C12—C18—O2	−21.8 (4)
C7—C6—C8—C9	−179.3 (3)	C13—C12—C18—N5	−21.0 (4)
N1—N2—C9—C8	0.4 (3)	C11—C12—C18—N5	159.9 (2)
C5—N2—C9—C8	174.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2	0.86	2.37	2.673 (3)	101
N4—H4···O2i	0.86	2.25	3.107 (3)	176
N5—H5···O1ii	0.86	2.16	2.915 (3)	146
C8—H8···O2i	0.93	2.50	3.168 (4)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O2	0.86	2.37	2.673 (3)	101
N4—H4⋯O2i	0.86	2.25	3.107 (3)	176
N5—H5⋯O1ii	0.86	2.16	2.915 (3)	146
C8—H8⋯O2i	0.93	2.50	3.168 (4)	129

Symmetry codes: (i) ; (ii) .