N-[4-Chloro-2-methyl-6-(N-methyl­car­bam­oyl)phen­yl]-1-(3-chloro-2-pyrid­yl)-3-trifluoro­meth­yl-1H-pyrazole-5-carboxamide

Yang, H.; Yu, H.; Li, B.

doi:10.1107/S1600536808037604

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2378

doi:10.1107/S1600536808037604

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N-[4-Chloro-2-methyl-6-(N-methylcarbamoyl)phenyl]-1-(3-chloro-2-pyridyl)-3-trifluoromethyl-1H-pyrazole-5-carboxamide

Huibin Yang,^a Haibo Yu ^a and Bin Li ^a ^*

^aAgrochemicals Division, Shenyang Research Institute of Chemical Industry, Shenyang 110021, People's Republic of China
^*Correspondence e-mail: libin1@sinochem.com

(Received 8 August 2008; accepted 16 November 2008; online 20 November 2008)

In the title compound, C₁₉H₁₄Cl₂F₃N₅O₂, which shows insecticidal activity, the dihedral angle between the pyrazole and pyridine rings is 68.15 (16)°. In the crystal structure, the molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds and an intramolecular N—H⋯O interaction also occurs. The F atoms of the –CF₃ 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_r = 472.25
Orthorhombic, F d d 2
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.082
S = 1.04
3565 reflections
310 parameters
49 restraints
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 1621 Friedel pairs
Flack parameter: −0.01 (7)

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) -x+1, -y+2, z; (ii) $[x+{\script{1\over 4}}, -y+{\script{7\over 4}}, z-{\script{1\over 4}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Anthranilamide compounds containing an N-pyridyl pyrazole grouping are a new class of inseticides showing potent activity against a broad spectrum of Lepidoptera and no-cross resistance to existing insecticides (Lahm et al., 2003) and their mode of action has been been established (Lahm et al., 2005). Anthranilamides show little effect on mammalian ryanodine receptors and as a result they show excellent insect versus mammalian selectivity. As part of our studies in this area, we now report the crystal structures of the title compound, (I), (Fig. 1) which possesses high insecticidal activity.

The pyrazole ring and pyridine rings are not coplanar, the dihedral angle formed by the least-squares planes of the rings being equal to 68.15 (16)°. The dihedral angle between the mean plane of the pyrazole ring and the plane of the C10/O1/N4 group is 23.4 (2)° and the dihedral angle between the mean plane of the phenyl ring and the plane of the C10/O1/N4 group is 59.9 (2)°.

An intramolecular N—H···O hydrogen bond (Table 1) is observed, which helps to establish the molecular conformation. Intermolecular N—H···O and C—H···O bonds result in a three-dimensional network.

Related literature top

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

Experimental top

The title compound was prepared by the literature method (Lahm et al., 2003). The crude products were purified by silica-gel column chromatography and then grown from acetone to afford colourless blocks of (I).

Anal. Calcd for C₁₂H₁₄N₄O₃: C, 48.32; H, 2.99; N, 14.83. Found: C, 48.47; H, 3.04; N, 14.66. ¹H NMR(CDCl₃): 2.19 (s, 3H, CH₃), 2.70 (d, J=4.5 Hz, 3H, CH₃), 7.30–7.31 (m, 2H, Ph), 7.57 (dd, 1H), 8.05 (d, J=8.1 Hz, 1H), 8.22 (br s, J=4.5 Hz, 1H, NH), 8.46 (d, J=4.8 Hz, 1H), 7.64 (s, 1H), 10.43 (s, 1H, NH).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

N-[4-Chloro-2-methyl-6-(N-methylcarbamoyl)phenyl]-1-(3-chloro-2- pyridyl)-3-trifluoromethyl-1H-pyrazole-5-carboxamide top

Crystal data top

C₁₉H₁₄Cl₂F₃N₅O₂	D_x = 1.524 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0387P)² + 8.8659P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3565 reflections	Δρ_max = 0.18 e Å⁻³
310 parameters	Δρ_min = −0.20 e Å⁻³
49 restraints	Absolute structure: Flack (1983), 1621 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (7)

Crystal data top

C₁₉H₁₄Cl₂F₃N₅O₂	V = 8233.9 (9) Å³
M_r = 472.25	Z = 16
Orthorhombic, Fdd2	Mo Kα radiation
a = 26.4612 (16) Å	µ = 0.37 mm⁻¹
b = 32.8657 (19) Å	T = 296 K
c = 9.4679 (6) Å	0.24 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD diffractometer	3565 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	3284 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.937	R_int = 0.021
10439 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.082	Δρ_max = 0.18 e Å⁻³
S = 1.04	Δρ_min = −0.20 e Å⁻³
3565 reflections	Absolute structure: Flack (1983), 1621 Friedel pairs
310 parameters	Absolute structure parameter: −0.01 (7)
49 restraints

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)
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, z; (ii) x+1/4, −y+7/4, z−1/4.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄Cl₂F₃N₅O₂
M_r	472.25
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	296
a, b, c (Å)	26.4612 (16), 32.8657 (19), 9.4679 (6)
V (Å³)	8233.9 (9)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.917, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	10439, 3565, 3284
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.082, 1.04
No. of reflections	3565
No. of parameters	310
No. of restraints	49
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20
Absolute structure	Flack (1983), 1621 Friedel pairs
Absolute structure parameter	−0.01 (7)

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, z; (ii) x+1/4, −y+7/4, z−1/4.

References

Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Lahm, G. P., Selby, T. P., Freudenberger, J. H., Stevenson, T. M., Myers, B. M., Seburyamo, G., Smith, B. K., Flexner, L., Clark, C. E. & Cordova, D. (2005). Bioorg. Med. Chem. Lett. 15, 4898–4906. Web of Science CrossRef PubMed CAS Google Scholar
Lahm, G. P., Selby, T. P. & Stevenson, T. M. (2003). International Patent Number WO 03/015 519. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 12| December 2008| Page o2378

doi:10.1107/S1600536808037604

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-[4-Chloro-2-methyl-6-(N-methyl­car­bam­oyl)phen­yl]-1-(3-chloro-2-pyrid­yl)-3-tri­fluoro­meth­yl-1H-pyrazole-5-carboxamide

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Experimental

Crystal data

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Supporting information

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organic compounds

N-[4-Chloro-2-methyl-6-(N-methylcarbamoyl)phenyl]-1-(3-chloro-2-pyridyl)-3-trifluoromethyl-1H-pyrazole-5-carboxamide