2-Chloro-N-{3-cyano-1-[2,6-dichloro-4-(trifluoro-meth-yl)phen-yl]-1H-pyrazol-5-yl}acetamide.

The title compound, C(13)H(6)Cl(3)F(3)N(4)O, was synthesized by the reaction of 5-amino-1-[2,6-dichloro-4-(trifluoro-meth-yl)phen-yl]-1H-pyrazole-3-carbonitrile and 2-chloro-acetyl chloride. The five-membered pyrazole ring makes a dihedral angle of 71.5 (3)° with the benzene ring. The -CF(3) group is disordered by rotation, and the F atoms are split over two sets of sites with occupancies of 0.59 (2) and 0.41 (2). The crystal structure features weak C-H⋯O and N-H⋯N inter-actions involving the carbonyl and cyano groups as acceptors.

Related literature

For biological properties of N-pyrazole derivatives, see: Cheng et al. (2008 ▶); Liu et al. (2010 ▶); Hatton et al. (1993 ▶). For related structures, see: Yang et al. (2004 ▶); Zhang et al. (2005 ▶); Zhong et al. (2004 ▶).

Experimental

Crystal data

C13H6Cl3F3N4O

M = 397.57

Triclinic,

a = 8.4190 (17) Å

b = 9.2650 (19) Å

c = 11.944 (2) Å

α = 69.77 (3)°

β = 76.74 (3)°

γ = 66.10 (3)°

V = 794.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.62 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.837, T max = 0.887

3133 measured reflections

2921 independent reflections

2313 reflections with I > 2σ(I)

R int = 0.030

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.155

S = 1.01

2921 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.58 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052743/bh2393sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052743/bh2393Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052743/bh2393Isup3.cml

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

C13H6Cl3F3N4O	Z = 2
Mr = 397.57	F(000) = 396
Triclinic, P1	Dx = 1.661 Mg m−3
Hall symbol: -P 1	Melting point: 483 K
a = 8.4190 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2650 (19) Å	Cell parameters from 25 reflections
c = 11.944 (2) Å	θ = 9–13°
α = 69.77 (3)°	µ = 0.62 mm−1
β = 76.74 (3)°	T = 293 K
γ = 66.10 (3)°	Block, colourless
V = 794.9 (3) Å3	0.30 × 0.20 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	2313 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 25.4°, θmin = 1.8°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −10→11
Tmin = 0.837, Tmax = 0.887	l = −14→14
3133 measured reflections	3 standard reflections every 200 reflections
2921 independent reflections	intensity decay: 1%

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.1P)2 + 0.320P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2921 reflections	Δρmax = 0.60 e Å−3
246 parameters	Δρmin = −0.58 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.195 (13)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O	0.3070 (3)	0.0918 (3)	0.0994 (3)	0.0713 (8)
Cl1	0.20070 (11)	0.26994 (9)	0.46773 (7)	0.0529 (3)
Cl2	0.04187 (13)	0.81751 (11)	0.09593 (7)	0.0636 (3)
Cl3	0.66610 (14)	0.09291 (16)	0.24189 (12)	0.0861 (4)
N1	0.0425 (3)	0.4846 (3)	0.2382 (2)	0.0414 (6)
C1	0.1882 (4)	0.4703 (3)	0.3992 (3)	0.0380 (6)
N2	−0.1343 (3)	0.5475 (3)	0.2373 (2)	0.0462 (6)
C2	0.2458 (4)	0.5460 (4)	0.4546 (3)	0.0444 (7)
H2B	0.2910	0.4894	0.5282	0.053*
C3	0.2352 (4)	0.7066 (4)	0.3993 (3)	0.0480 (7)
N3	−0.4748 (4)	0.5210 (5)	0.1439 (4)	0.0816 (11)
N4	0.3004 (3)	0.2913 (4)	0.1692 (3)	0.0510 (7)
H4A	0.3625	0.3317	0.1884	0.061*
C4	0.1707 (4)	0.7917 (4)	0.2891 (3)	0.0482 (7)
H4B	0.1657	0.8996	0.2520	0.058*
C5	0.1144 (4)	0.7150 (4)	0.2353 (3)	0.0431 (7)
C6	0.1175 (3)	0.5552 (3)	0.2906 (2)	0.0371 (6)
C7	0.2921 (6)	0.7937 (5)	0.4592 (5)	0.0759 (12)
C8	−0.1616 (4)	0.4631 (4)	0.1792 (3)	0.0468 (7)
C9	−0.0098 (4)	0.3489 (4)	0.1413 (3)	0.0504 (8)
H9A	0.0011	0.2764	0.0998	0.060*
C10	0.1202 (4)	0.3680 (4)	0.1793 (3)	0.0419 (7)
C11	−0.3373 (5)	0.4970 (5)	0.1602 (3)	0.0597 (9)
C12	0.3826 (4)	0.1554 (4)	0.1304 (3)	0.0511 (8)
C13	0.5789 (5)	0.0841 (6)	0.1261 (4)	0.0791 (13)
H13A	0.6268	0.1419	0.0503	0.095*
H13B	0.6178	−0.0302	0.1271	0.095*
F1	0.193 (2)	0.9401 (14)	0.447 (3)	0.155 (10)	0.59 (2)
F2	0.4449 (12)	0.8100 (17)	0.3936 (8)	0.104 (3)	0.59 (2)
F3	0.3470 (18)	0.7085 (13)	0.5612 (6)	0.111 (4)	0.59 (2)
F1'	0.1496 (12)	0.851 (3)	0.5471 (17)	0.111 (6)	0.41 (2)
F2'	0.327 (6)	0.913 (4)	0.4027 (11)	0.169 (13)	0.41 (2)
F3'	0.3932 (17)	0.6929 (17)	0.5431 (17)	0.135 (8)	0.41 (2)

	U11	U22	U33	U12	U13	U23
O	0.0581 (15)	0.0791 (18)	0.097 (2)	−0.0240 (13)	−0.0006 (14)	−0.0539 (16)
Cl1	0.0595 (5)	0.0366 (4)	0.0579 (5)	−0.0150 (3)	−0.0143 (4)	−0.0052 (3)
Cl2	0.0760 (6)	0.0575 (5)	0.0474 (5)	−0.0184 (4)	−0.0215 (4)	0.0000 (4)
Cl3	0.0623 (6)	0.0942 (8)	0.1011 (8)	−0.0006 (5)	−0.0307 (6)	−0.0455 (7)
N1	0.0354 (13)	0.0464 (14)	0.0460 (13)	−0.0133 (11)	−0.0082 (10)	−0.0167 (11)
C1	0.0340 (14)	0.0352 (14)	0.0432 (15)	−0.0093 (11)	−0.0075 (11)	−0.0105 (12)
N2	0.0336 (13)	0.0546 (15)	0.0508 (15)	−0.0133 (11)	−0.0082 (11)	−0.0159 (12)
C2	0.0419 (16)	0.0485 (17)	0.0454 (16)	−0.0113 (13)	−0.0148 (13)	−0.0157 (13)
C3	0.0396 (16)	0.0499 (18)	0.0607 (19)	−0.0134 (14)	−0.0091 (14)	−0.0236 (15)
N3	0.0492 (19)	0.114 (3)	0.097 (3)	−0.0287 (19)	−0.0217 (17)	−0.040 (2)
N4	0.0399 (14)	0.0645 (17)	0.0633 (17)	−0.0206 (12)	−0.0029 (12)	−0.0346 (14)
C4	0.0478 (18)	0.0361 (15)	0.0593 (19)	−0.0151 (13)	−0.0093 (14)	−0.0093 (13)
C5	0.0390 (15)	0.0418 (16)	0.0433 (15)	−0.0090 (12)	−0.0095 (12)	−0.0089 (12)
C6	0.0320 (14)	0.0402 (15)	0.0407 (15)	−0.0103 (11)	−0.0059 (11)	−0.0150 (12)
C7	0.075 (3)	0.058 (2)	0.112 (4)	−0.018 (2)	−0.040 (3)	−0.031 (2)
C8	0.0410 (17)	0.0599 (19)	0.0465 (16)	−0.0212 (14)	−0.0118 (13)	−0.0149 (14)
C9	0.0486 (18)	0.063 (2)	0.0535 (18)	−0.0246 (15)	−0.0079 (14)	−0.0256 (15)
C10	0.0407 (16)	0.0487 (16)	0.0420 (15)	−0.0174 (13)	−0.0047 (12)	−0.0174 (13)
C11	0.053 (2)	0.077 (2)	0.058 (2)	−0.0258 (18)	−0.0128 (16)	−0.0231 (18)
C12	0.0449 (18)	0.063 (2)	0.0556 (19)	−0.0200 (16)	0.0018 (14)	−0.0334 (16)
C13	0.044 (2)	0.116 (4)	0.095 (3)	−0.013 (2)	−0.0016 (19)	−0.072 (3)
F1	0.120 (7)	0.087 (7)	0.31 (3)	0.014 (6)	−0.107 (12)	−0.124 (12)
F2	0.106 (6)	0.127 (7)	0.122 (5)	−0.082 (5)	−0.039 (4)	−0.020 (5)
F3	0.200 (10)	0.138 (7)	0.059 (4)	−0.118 (8)	−0.023 (4)	−0.027 (4)
F1'	0.075 (5)	0.149 (12)	0.155 (11)	−0.020 (6)	−0.009 (5)	−0.124 (10)
F2'	0.35 (4)	0.16 (2)	0.100 (7)	−0.21 (3)	−0.044 (17)	−0.007 (11)
F3'	0.074 (5)	0.128 (9)	0.230 (19)	0.043 (7)	−0.106 (8)	−0.119 (12)

O—C12	1.205 (4)	N4—H4A	0.8600
Cl1—C1	1.720 (3)	C4—C5	1.368 (4)
Cl2—C5	1.717 (3)	C4—H4B	0.9300
Cl3—C13	1.747 (4)	C5—C6	1.390 (4)
N1—C10	1.353 (4)	C7—F2'	1.192 (11)
N1—N2	1.362 (3)	C7—F1	1.249 (8)
N1—C6	1.420 (4)	C7—F3	1.273 (9)
C1—C2	1.382 (4)	C7—F3'	1.304 (13)
C1—C6	1.387 (4)	C7—F2	1.381 (9)
N2—C8	1.319 (4)	C7—F1'	1.454 (11)
C2—C3	1.378 (5)	C8—C9	1.389 (5)
C2—H2B	0.9300	C8—C11	1.437 (4)
C3—C4	1.383 (5)	C9—C10	1.369 (4)
C3—C7	1.504 (5)	C9—H9A	0.9300
N3—C11	1.137 (5)	C12—C13	1.506 (5)
N4—C12	1.353 (4)	C13—H13A	0.9700
N4—C10	1.387 (4)	C13—H13B	0.9700
C10—N1—N2	111.9 (2)	F2'—C7—F1'	103.7 (13)
C10—N1—C6	130.1 (2)	F3'—C7—F1'	91.6 (9)
N2—N1—C6	117.8 (2)	F2'—C7—F3'	114.9 (16)
C2—C1—C6	120.8 (3)	F1—C7—C3	112.7 (5)
C2—C1—Cl1	119.3 (2)	F2—C7—C3	106.0 (6)
C6—C1—Cl1	119.9 (2)	F3—C7—C3	115.0 (5)
C8—N2—N1	103.3 (2)	F1'—C7—C3	107.6 (5)
C3—C2—C1	119.0 (3)	F2'—C7—C3	120.9 (7)
C3—C2—H2B	120.5	F3'—C7—C3	113.0 (7)
C1—C2—H2B	120.5	N2—C8—C9	113.8 (3)
C2—C3—C4	121.2 (3)	N2—C8—C11	119.2 (3)
C2—C3—C7	120.2 (3)	C9—C8—C11	127.1 (3)
C4—C3—C7	118.6 (3)	C10—C9—C8	103.8 (3)
C12—N4—C10	122.7 (3)	C10—C9—H9A	128.1
C12—N4—H4A	118.6	C8—C9—H9A	128.1
C10—N4—H4A	118.6	N1—C10—C9	107.2 (3)
C5—C4—C3	119.0 (3)	N1—C10—N4	120.4 (3)
C5—C4—H4B	120.5	C9—C10—N4	132.4 (3)
C3—C4—H4B	120.5	N3—C11—C8	178.4 (4)
C4—C5—C6	121.2 (3)	O—C12—N4	123.4 (3)
C4—C5—Cl2	119.2 (2)	O—C12—C13	120.0 (3)
C6—C5—Cl2	119.6 (2)	N4—C12—C13	116.7 (3)
C1—C6—C5	118.7 (3)	C12—C13—Cl3	115.8 (2)
C1—C6—N1	121.4 (3)	C12—C13—H13A	108.3
C5—C6—N1	119.8 (3)	Cl3—C13—H13A	108.3
F1—C7—F2	102.2 (9)	C12—C13—H13B	108.3
F1—C7—F3	118.1 (10)	Cl3—C13—H13B	108.3
F3—C7—F2	100.1 (6)	H13A—C13—H13B	107.4
C10—N1—N2—C8	1.6 (3)	C4—C3—C7—F1	39.4 (16)
C6—N1—N2—C8	177.3 (3)	C2—C3—C7—F3	−0.4 (9)
C6—C1—C2—C3	−1.3 (4)	C4—C3—C7—F3	178.8 (8)
Cl1—C1—C2—C3	−179.9 (2)	C2—C3—C7—F3'	18.7 (11)
C1—C2—C3—C4	−1.0 (5)	C4—C3—C7—F3'	−162.0 (10)
C1—C2—C3—C7	178.2 (3)	C2—C3—C7—F2	109.2 (6)
C2—C3—C4—C5	0.9 (5)	C4—C3—C7—F2	−71.6 (6)
C7—C3—C4—C5	−178.3 (3)	C2—C3—C7—F1'	−80.8 (11)
C3—C4—C5—C6	1.4 (5)	C4—C3—C7—F1'	98.4 (11)
C3—C4—C5—Cl2	−177.6 (2)	N1—N2—C8—C9	−0.6 (4)
C2—C1—C6—C5	3.5 (4)	N1—N2—C8—C11	−179.8 (3)
Cl1—C1—C6—C5	−177.8 (2)	N2—C8—C9—C10	−0.6 (4)
C2—C1—C6—N1	−173.9 (2)	C11—C8—C9—C10	178.6 (3)
Cl1—C1—C6—N1	4.8 (4)	N2—N1—C10—C9	−2.0 (3)
C4—C5—C6—C1	−3.6 (4)	C6—N1—C10—C9	−177.0 (3)
Cl2—C5—C6—C1	175.4 (2)	N2—N1—C10—N4	179.1 (3)
C4—C5—C6—N1	173.8 (3)	C6—N1—C10—N4	4.0 (5)
Cl2—C5—C6—N1	−7.1 (4)	C8—C9—C10—N1	1.5 (4)
C10—N1—C6—C1	−76.2 (4)	C8—C9—C10—N4	−179.8 (3)
N2—N1—C6—C1	109.0 (3)	C12—N4—C10—N1	168.1 (3)
C10—N1—C6—C5	106.4 (4)	C12—N4—C10—C9	−10.5 (6)
N2—N1—C6—C5	−68.3 (3)	C10—N4—C12—O	1.4 (6)
C2—C3—C7—F2'	161 (3)	C10—N4—C12—C13	−179.0 (3)
C4—C3—C7—F2'	−20 (3)	O—C12—C13—Cl3	−143.6 (4)
C2—C3—C7—F1	−139.8 (16)	N4—C12—C13—Cl3	36.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N3i	0.86	2.49	3.280 (5)	153.
C4—H4B···Oii	0.93	2.53	3.349 (5)	148.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N3i	0.86	2.49	3.280 (5)	153
C4—H4B⋯Oii	0.93	2.53	3.349 (5)	148

Symmetry codes: (i) ; (ii) .