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The mol­ecule of the title compound, C19H11Cl2F3N4O, is a tricyclic amide with an overall U shape. The dihedral angles between the pyrazole and outermost benzene and phenyl rings are 89.4 (1) and 114.5 (1)°, respectively. In the crystal structure, inter­molecular N—H...N hydrogen bonds, with an N(amide)...N(cyano) separation of 3.220 (7) Å, link the mol­ecules into linear chains along the [110] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805032514/cv6589sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805032514/cv6589Isup2.hkl
Contains datablock I

CCDC reference: 289705

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.055
  • wR factor = 0.153
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C1
Author Response: see _publ_section_exptl_refinement

Alert level B PLAT213_ALERT_2_B Atom F2 has ADP max/min Ratio ............. 4.20 prolat
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C11 ... 1.45 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. F3 .. 3.18 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 41 N2 -C8 -C11 -N3 148.00 8.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 42 C9 -C8 -C11 -N3 -30.00 8.00 1.555 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.13 From the CIF: _reflns_number_total 2389 Count of symmetry unique reflns 1758 Completeness (_total/calc) 135.89% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 631 Fraction of Friedel pairs measured 0.359 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 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 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-(phenylacetamido)-1H-pyrazole- 3-carbonitrile top
Crystal data top
C19H11Cl2F3N4OF(000) = 888
Mr = 439.22Dx = 1.490 Mg m3
Monoclinic, CcMelting point: 463 K
Hall symbol: C -2ycMo Kα radiation, λ = 0.71073 Å
a = 15.302 (8) ÅCell parameters from 2534 reflections
b = 8.604 (5) Åθ = 2.7–25.0°
c = 14.872 (8) ŵ = 0.38 mm1
β = 90.25 (1)°T = 298 K
V = 1957.9 (19) Å3Block, colourless
Z = 40.42 × 0.28 × 0.25 mm
Data collection top
Bruker APEX area-detector
diffractometer
2389 independent reflections
Radiation source: fine-focus sealed tube2254 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 25.1°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1718
Tmin = 0.858, Tmax = 0.912k = 910
4794 measured reflectionsl = 1712
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.153 w = 1/[σ2(Fo2) + (0.0814P)2 + 2.8261P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2389 reflectionsΔρmax = 0.52 e Å3
262 parametersΔρmin = 0.27 e Å3
2 restraintsAbsolute structure: Flack (1983), 631 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.13 (13)
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
xyzUiso*/Ueq
Cl10.27732 (11)0.9258 (2)0.76138 (11)0.0668 (5)
Cl20.32840 (17)0.55890 (18)0.47378 (14)0.0870 (7)
F10.4710 (6)1.2302 (9)0.5406 (4)0.169 (4)
F20.5016 (7)1.0871 (6)0.4366 (9)0.247 (7)
F30.3919 (5)1.2133 (7)0.4338 (5)0.139 (2)
O10.4156 (3)0.2752 (4)0.7695 (3)0.0533 (10)
N10.2686 (3)0.6295 (5)0.6584 (3)0.0412 (10)
N20.1805 (3)0.6007 (5)0.6496 (3)0.0458 (11)
N30.0223 (3)0.3275 (6)0.7057 (4)0.0623 (14)
N40.4000 (3)0.5241 (5)0.7209 (3)0.0448 (11)
H40.42630.61040.71000.054*
C10.4394 (5)1.1302 (7)0.4845 (5)0.0621 (16)
C20.3930 (4)0.9972 (6)0.5268 (4)0.0497 (13)
C30.3596 (3)1.0199 (6)0.6125 (4)0.0452 (12)
H30.36581.11540.64110.054*
C40.3171 (3)0.8992 (6)0.6546 (4)0.0419 (11)
C50.3081 (3)0.7566 (6)0.6130 (4)0.0389 (10)
C60.3398 (4)0.7364 (6)0.5262 (4)0.0484 (13)
C70.3821 (4)0.8593 (7)0.4836 (4)0.0510 (13)
H70.40310.84690.42540.061*
C80.1704 (3)0.4701 (6)0.6954 (4)0.0434 (12)
C90.2479 (3)0.4122 (6)0.7327 (4)0.0444 (12)
H90.25500.32270.76700.053*
C100.3102 (3)0.5158 (6)0.7078 (4)0.0409 (11)
C110.0857 (4)0.3953 (6)0.7010 (4)0.0471 (13)
C120.4489 (3)0.3975 (6)0.7511 (4)0.0425 (12)
C130.5469 (3)0.4271 (7)0.7575 (4)0.0471 (13)
H13A0.57730.35510.71830.057*
H13B0.55930.53160.73670.057*
C140.5810 (3)0.4084 (6)0.8523 (4)0.0432 (12)
C150.5952 (4)0.5388 (8)0.9061 (5)0.0601 (16)
H150.58290.63710.88330.072*
C160.6271 (5)0.5243 (11)0.9921 (6)0.078 (2)
H160.63590.61261.02700.094*
C170.6457 (4)0.3815 (10)1.0264 (5)0.074 (2)
H170.66730.37291.08460.089*
C180.6324 (5)0.2446 (9)0.9736 (5)0.073 (2)
H180.64490.14660.99670.088*
C190.6006 (4)0.2622 (7)0.8878 (4)0.0558 (14)
H190.59180.17440.85240.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0669 (9)0.0783 (10)0.0551 (9)0.0188 (8)0.0187 (7)0.0115 (8)
Cl20.1396 (18)0.0487 (8)0.0728 (12)0.0182 (10)0.0253 (11)0.0158 (8)
F10.235 (8)0.165 (6)0.105 (5)0.150 (6)0.004 (5)0.028 (4)
F20.253 (10)0.060 (3)0.430 (17)0.008 (4)0.269 (12)0.049 (6)
F30.168 (6)0.086 (3)0.161 (6)0.022 (3)0.015 (5)0.069 (4)
O10.055 (2)0.041 (2)0.064 (3)0.0106 (18)0.013 (2)0.0079 (17)
N10.029 (2)0.036 (2)0.058 (3)0.0068 (17)0.0001 (19)0.0102 (19)
N20.033 (2)0.045 (2)0.059 (3)0.0057 (19)0.001 (2)0.004 (2)
N30.042 (3)0.064 (3)0.081 (4)0.014 (3)0.001 (2)0.008 (3)
N40.034 (2)0.037 (2)0.063 (3)0.0075 (18)0.002 (2)0.011 (2)
C10.065 (4)0.050 (3)0.070 (4)0.013 (3)0.009 (3)0.012 (3)
C20.047 (3)0.043 (3)0.059 (4)0.004 (3)0.001 (3)0.011 (3)
C30.040 (3)0.040 (3)0.055 (3)0.007 (2)0.002 (2)0.002 (2)
C40.033 (3)0.045 (3)0.047 (3)0.002 (2)0.000 (2)0.003 (2)
C50.033 (2)0.039 (2)0.045 (3)0.0007 (19)0.004 (2)0.0070 (19)
C60.056 (3)0.038 (3)0.051 (3)0.004 (2)0.001 (2)0.002 (2)
C70.065 (3)0.048 (3)0.040 (3)0.006 (3)0.010 (2)0.006 (2)
C80.035 (3)0.050 (3)0.045 (3)0.010 (2)0.003 (2)0.004 (2)
C90.042 (3)0.038 (3)0.054 (3)0.007 (2)0.004 (2)0.011 (2)
C100.035 (3)0.041 (2)0.047 (3)0.002 (2)0.004 (2)0.000 (2)
C110.039 (3)0.045 (3)0.057 (4)0.007 (3)0.003 (2)0.003 (2)
C120.041 (3)0.050 (3)0.036 (3)0.003 (2)0.001 (2)0.001 (2)
C130.031 (3)0.058 (3)0.053 (3)0.001 (2)0.004 (2)0.012 (3)
C140.026 (2)0.055 (3)0.049 (3)0.001 (2)0.003 (2)0.001 (2)
C150.052 (3)0.059 (4)0.069 (4)0.002 (3)0.002 (3)0.007 (3)
C160.069 (5)0.089 (5)0.077 (5)0.009 (4)0.010 (4)0.024 (4)
C170.059 (4)0.105 (6)0.058 (4)0.012 (4)0.015 (3)0.003 (4)
C180.076 (5)0.079 (5)0.065 (4)0.009 (4)0.003 (4)0.021 (4)
C190.061 (3)0.055 (3)0.052 (3)0.002 (3)0.002 (3)0.001 (3)
Geometric parameters (Å, º) top
Cl1—C41.716 (6)C6—C71.393 (8)
Cl2—C61.723 (6)C7—H70.9300
F1—C11.293 (9)C8—C91.401 (8)
F2—C11.245 (9)C8—C111.449 (8)
F3—C11.268 (9)C9—C101.356 (7)
O1—C121.201 (6)C9—H90.9300
N1—N21.377 (6)C12—C131.524 (7)
N1—C101.379 (6)C13—C141.512 (8)
N1—C51.421 (7)C13—H13A0.9700
N2—C81.323 (7)C13—H13B0.9700
N3—C111.134 (7)C14—C151.394 (8)
N4—C101.390 (6)C14—C191.397 (8)
N4—C121.396 (7)C15—C161.375 (11)
N4—H40.8600C15—H150.9300
C1—C21.486 (8)C16—C171.361 (12)
C2—C71.359 (8)C16—H160.9300
C2—C31.387 (8)C17—C181.430 (11)
C3—C41.376 (8)C17—H170.9300
C3—H30.9300C18—C191.374 (9)
C4—C51.380 (7)C18—H180.9300
C5—C61.390 (8)C19—H190.9300
N2—N1—C10112.0 (4)C10—C9—C8104.7 (4)
N2—N1—C5120.7 (4)C10—C9—H9127.7
C10—N1—C5127.1 (4)C8—C9—H9127.7
C8—N2—N1102.6 (4)C9—C10—N1106.7 (4)
C10—N4—C12122.4 (4)C9—C10—N4133.6 (5)
C10—N4—H4118.8N1—C10—N4119.7 (4)
C12—N4—H4118.8N3—C11—C8175.3 (6)
F2—C1—F3105.4 (9)O1—C12—N4122.0 (5)
F2—C1—F1106.3 (9)O1—C12—C13123.3 (5)
F3—C1—F1102.9 (7)N4—C12—C13114.7 (4)
F2—C1—C2112.2 (6)C14—C13—C12112.4 (4)
F3—C1—C2114.3 (6)C14—C13—H13A109.1
F1—C1—C2114.7 (6)C12—C13—H13A109.1
C7—C2—C3120.8 (5)C14—C13—H13B109.1
C7—C2—C1122.0 (6)C12—C13—H13B109.1
C3—C2—C1117.2 (5)H13A—C13—H13B107.9
C4—C3—C2119.0 (5)C15—C14—C19118.4 (5)
C4—C3—H3120.5C15—C14—C13120.2 (5)
C2—C3—H3120.5C19—C14—C13121.5 (5)
C3—C4—C5121.0 (5)C16—C15—C14121.1 (6)
C3—C4—Cl1119.2 (4)C16—C15—H15119.5
C5—C4—Cl1119.8 (4)C14—C15—H15119.5
C4—C5—C6119.5 (5)C17—C16—C15120.3 (7)
C4—C5—N1120.9 (5)C17—C16—H16119.8
C6—C5—N1119.6 (5)C15—C16—H16119.8
C5—C6—C7119.3 (5)C16—C17—C18120.6 (7)
C5—C6—Cl2119.7 (4)C16—C17—H17119.7
C7—C6—Cl2120.9 (5)C18—C17—H17119.7
C2—C7—C6120.3 (5)C19—C18—C17118.0 (6)
C2—C7—H7119.8C19—C18—H18121.0
C6—C7—H7119.8C17—C18—H18121.0
N2—C8—C9114.0 (5)C18—C19—C14121.7 (6)
N2—C8—C11120.8 (5)C18—C19—H19119.1
C9—C8—C11125.2 (5)C14—C19—H19119.1
C10—N1—N2—C80.9 (6)N1—N2—C8—C90.6 (6)
C5—N1—N2—C8175.7 (5)N1—N2—C8—C11178.2 (5)
F2—C1—C2—C735.8 (11)N2—C8—C9—C100.0 (7)
F3—C1—C2—C784.3 (9)C11—C8—C9—C10177.6 (5)
F1—C1—C2—C7157.2 (7)C8—C9—C10—N10.5 (6)
F2—C1—C2—C3145.2 (10)C8—C9—C10—N4178.2 (6)
F3—C1—C2—C394.8 (8)N2—N1—C10—C90.9 (6)
F1—C1—C2—C323.7 (9)C5—N1—C10—C9175.3 (5)
C7—C2—C3—C41.8 (8)N2—N1—C10—N4178.0 (5)
C1—C2—C3—C4179.2 (5)C5—N1—C10—N43.6 (8)
C2—C3—C4—C50.5 (8)C12—N4—C10—C914.0 (10)
C2—C3—C4—Cl1178.9 (4)C12—N4—C10—N1164.6 (5)
C3—C4—C5—C62.2 (7)N2—C8—C11—N3148 (8)
Cl1—C4—C5—C6179.4 (4)C9—C8—C11—N330 (8)
C3—C4—C5—N1176.5 (4)C10—N4—C12—O11.8 (8)
Cl1—C4—C5—N11.9 (7)C10—N4—C12—C13177.5 (5)
N2—N1—C5—C493.0 (6)O1—C12—C13—C1461.6 (7)
C10—N1—C5—C493.0 (7)N4—C12—C13—C14119.1 (5)
N2—N1—C5—C688.3 (6)C12—C13—C14—C1599.5 (6)
C10—N1—C5—C685.7 (7)C12—C13—C14—C1981.6 (6)
C4—C5—C6—C71.7 (8)C19—C14—C15—C160.4 (9)
N1—C5—C6—C7177.0 (5)C13—C14—C15—C16179.3 (6)
C4—C5—C6—Cl2179.8 (4)C14—C15—C16—C170.2 (11)
N1—C5—C6—Cl21.5 (7)C15—C16—C17—C180.1 (11)
C3—C2—C7—C62.2 (8)C16—C17—C18—C190.2 (11)
C1—C2—C7—C6178.8 (6)C17—C18—C19—C140.4 (10)
C5—C6—C7—C20.5 (8)C15—C14—C19—C180.5 (9)
Cl2—C6—C7—C2178.0 (5)C13—C14—C19—C18179.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···N3i0.862.383.220 (7)167
Symmetry code: (i) x+1/2, y+1/2, z.
 

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