N-{3-Cyano-1-[2,6-di­chloro-4-(tri­fluoro­methyl)­phenyl]-1H-pyrazol-5-yl}acet­amide

The title compound, C₁₃H₇Cl₂F₃N₄O, has normal bond lengths and angles. The crystal packing is stabilized by intermolecular N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.064
• wR factor = 0.170
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT213_ALERT_2_C Atom F3      has ADP max/min Ratio .............       3.40 prolat
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.41
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C10    -   C11    ...       1.44 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

N-{3-Cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl}acetamide

Crystal data

C13H7Cl2F3N4O	F(000) = 1456
Mr = 363.13	Dx = 1.559 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C2yc	Cell parameters from 2156 reflections
a = 18.8282 (6) Å	θ = 2.6–25.2°
b = 8.6541 (3) Å	µ = 0.46 mm^−1
c = 19.0766 (6) Å	T = 298 K
β = 95.583 (1)°	Block, colorless
V = 3093.62 (18) Å^3	0.44 × 0.16 × 0.13 mm
Z = 8

Data collection

Bruker SMART APEX area-detector diffractometer	2768 independent reflections
Radiation source: fine-focus sealed tube	2373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.3°, θmin = 2.2°
Absorption correction: integration (SADABS; Bruker, 2002)	h = −22→20
Tmin = 0.824, Tmax = 0.943	k = −10→8
7655 measured reflections	l = −18→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ^2(Fo^2) + (0.079P)^2 + 4.3533P] where P = (Fo^2 + 2Fc^2)/3
2768 reflections	(Δ/σ)max = 0.003
209 parameters	Δρmax = 0.65 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.01946 (5)	0.58378 (11)	0.11136 (5)	0.0661 (3)
Cl2	0.75365 (5)	0.45026 (11)	0.00088 (6)	0.0735 (4)
O1	0.81662 (19)	0.4727 (3)	0.29753 (14)	0.0835 (9)
N1	0.88236 (15)	0.4100 (3)	0.10069 (13)	0.0437 (6)
N2	0.89015 (16)	0.2609 (3)	0.08006 (14)	0.0495 (7)
N3	0.85589 (17)	0.5641 (3)	0.19798 (14)	0.0515 (7)
H3	0.8644	0.6456	0.1744	0.062*
N4	0.8823 (3)	−0.1145 (3)	0.1390 (2)	0.0890 (13)
F1	0.83902 (17)	0.9102 (3)	−0.14120 (14)	0.0924 (9)
F2	0.94540 (17)	0.8529 (4)	−0.14565 (16)	0.1202 (12)
F3	0.9151 (3)	1.0206 (3)	−0.07088 (16)	0.1503 (18)
C1	0.8994 (3)	0.8880 (5)	−0.1002 (2)	0.0735 (12)
C2	0.8945 (2)	0.7617 (3)	−0.04721 (16)	0.0506 (8)
C3	0.95232 (19)	0.7347 (3)	0.00116 (17)	0.0498 (8)
H3A	0.9936	0.7934	0.0006	0.060*
C4	0.94806 (18)	0.6198 (3)	0.05024 (16)	0.0446 (7)
C5	0.88713 (16)	0.5305 (3)	0.05079 (14)	0.0393 (7)
C6	0.83010 (18)	0.5599 (3)	0.00141 (17)	0.0470 (7)
C7	0.8332 (2)	0.6753 (4)	−0.04808 (17)	0.0524 (8)
H7	0.7947	0.6941	−0.0813	0.063*
C8	0.86663 (18)	0.4215 (3)	0.16857 (16)	0.0441 (7)
C9	0.8647 (2)	0.2742 (3)	0.19370 (17)	0.0537 (8)
H9	0.8558	0.2425	0.2386	0.064*
C10	0.87919 (19)	0.1825 (3)	0.13742 (17)	0.0500 (8)
C11	0.8817 (2)	0.0160 (4)	0.1367 (2)	0.0659 (11)
C12	0.8322 (2)	0.5814 (4)	0.26343 (17)	0.0524 (8)
C13	0.8274 (2)	0.7454 (4)	0.2878 (2)	0.0666 (10)
H13A	0.8107	0.7472	0.3337	0.100*
H13B	0.7948	0.8015	0.2554	0.100*
H13C	0.8738	0.7924	0.2899	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0685 (6)	0.0588 (6)	0.0672 (6)	−0.0052 (4)	−0.0126 (4)	0.0037 (4)
Cl2	0.0653 (6)	0.0512 (6)	0.1017 (8)	−0.0170 (4)	−0.0037 (5)	0.0105 (5)
O1	0.146 (3)	0.0528 (16)	0.0565 (16)	−0.0066 (17)	0.0344 (17)	0.0017 (13)
N1	0.0649 (16)	0.0236 (12)	0.0434 (14)	0.0005 (11)	0.0094 (12)	0.0024 (10)
N2	0.0747 (18)	0.0243 (12)	0.0511 (15)	0.0008 (11)	0.0145 (13)	−0.0008 (11)
N3	0.084 (2)	0.0264 (12)	0.0457 (15)	0.0033 (12)	0.0120 (13)	0.0012 (11)
N4	0.157 (4)	0.0279 (16)	0.089 (3)	0.0097 (19)	0.046 (3)	0.0071 (15)
F1	0.131 (2)	0.0687 (16)	0.0742 (16)	0.0045 (14)	−0.0066 (15)	0.0311 (12)
F2	0.119 (2)	0.153 (3)	0.095 (2)	0.006 (2)	0.0389 (18)	0.064 (2)
F3	0.289 (5)	0.0559 (16)	0.093 (2)	−0.075 (2)	−0.047 (3)	0.0298 (15)
C1	0.110 (3)	0.057 (2)	0.053 (2)	−0.019 (2)	0.009 (2)	0.0155 (18)
C2	0.082 (2)	0.0320 (15)	0.0385 (16)	−0.0028 (15)	0.0097 (15)	0.0010 (13)
C3	0.067 (2)	0.0339 (16)	0.0499 (18)	−0.0120 (14)	0.0115 (15)	−0.0024 (13)
C4	0.0598 (19)	0.0329 (15)	0.0407 (16)	−0.0011 (13)	0.0030 (13)	−0.0020 (12)
C5	0.0587 (18)	0.0230 (13)	0.0373 (15)	0.0003 (12)	0.0098 (13)	0.0003 (11)
C6	0.0584 (19)	0.0298 (14)	0.0525 (18)	−0.0030 (13)	0.0034 (15)	−0.0007 (13)
C7	0.070 (2)	0.0372 (17)	0.0485 (18)	0.0004 (15)	−0.0031 (15)	0.0013 (14)
C8	0.0638 (19)	0.0280 (14)	0.0409 (16)	0.0017 (13)	0.0072 (14)	0.0000 (12)
C9	0.084 (2)	0.0318 (16)	0.0466 (18)	0.0016 (15)	0.0155 (16)	0.0065 (13)
C10	0.070 (2)	0.0249 (14)	0.0564 (19)	0.0011 (14)	0.0143 (16)	0.0038 (13)
C11	0.108 (3)	0.0324 (19)	0.062 (2)	0.0022 (18)	0.028 (2)	0.0021 (16)
C12	0.074 (2)	0.0396 (18)	0.0441 (18)	0.0027 (15)	0.0061 (16)	−0.0018 (14)
C13	0.094 (3)	0.047 (2)	0.060 (2)	0.0114 (19)	0.0130 (19)	−0.0125 (17)

Geometric parameters (Å, º)

Cl1—C4	1.720 (3)	C2—C3	1.377 (5)
Cl2—C6	1.723 (3)	C3—C4	1.373 (4)
O1—C12	1.196 (4)	C3—H3A	0.9300
N1—C8	1.360 (4)	C4—C5	1.384 (4)
N1—N2	1.361 (3)	C5—C6	1.381 (4)
N1—C5	1.421 (3)	C6—C7	1.379 (4)
N2—C10	1.321 (4)	C7—H7	0.9300
N3—C12	1.375 (4)	C8—C9	1.364 (4)
N3—C8	1.378 (4)	C9—C10	1.383 (5)
N3—H3	0.8600	C9—H9	0.9300
N4—C11	1.130 (5)	C10—C11	1.441 (5)
F1—C1	1.330 (5)	C12—C13	1.499 (5)
F2—C1	1.319 (5)	C13—H13A	0.9600
F3—C1	1.298 (5)	C13—H13B	0.9600
C1—C2	1.497 (5)	C13—H13C	0.9600
C2—C7	1.373 (5)
C8—N1—N2	112.6 (2)	C7—C6—C5	121.2 (3)
C8—N1—C5	128.2 (2)	C7—C6—Cl2	119.1 (3)
N2—N1—C5	119.1 (2)	C5—C6—Cl2	119.7 (2)
C10—N2—N1	102.6 (2)	C2—C7—C6	118.5 (3)
C12—N3—C8	122.7 (3)	C2—C7—H7	120.7
C12—N3—H3	118.6	C6—C7—H7	120.7
C8—N3—H3	118.6	N1—C8—C9	106.4 (3)
F3—C1—F2	110.6 (4)	N1—C8—N3	120.5 (3)
F3—C1—F1	105.7 (4)	C9—C8—N3	133.1 (3)
F2—C1—F1	103.0 (3)	C8—C9—C10	104.5 (3)
F3—C1—C2	112.4 (3)	C8—C9—H9	127.8
F2—C1—C2	111.3 (4)	C10—C9—H9	127.8
F1—C1—C2	113.3 (4)	N2—C10—C9	114.0 (3)
C7—C2—C3	121.6 (3)	N2—C10—C11	119.9 (3)
C7—C2—C1	119.8 (3)	C9—C10—C11	126.1 (3)
C3—C2—C1	118.6 (3)	N4—C11—C10	176.8 (4)
C4—C3—C2	119.0 (3)	O1—C12—N3	121.8 (3)
C4—C3—H3A	120.5	O1—C12—C13	123.4 (3)
C2—C3—H3A	120.5	N3—C12—C13	114.8 (3)
C3—C4—C5	120.8 (3)	C12—C13—H13A	109.5
C3—C4—Cl1	120.0 (3)	C12—C13—H13B	109.5
C5—C4—Cl1	119.2 (2)	H13A—C13—H13B	109.5
C6—C5—C4	118.8 (3)	C12—C13—H13C	109.5
C6—C5—N1	119.8 (3)	H13A—C13—H13C	109.5
C4—C5—N1	121.4 (3)	H13B—C13—H13C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N4^i	0.86	2.22	3.060 (4)	166

Symmetry code: (i) x, y+1, z.