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The mol­ecular structure of the title tricyclic imine, C19H10Cl3F3N4, has an overall Y-shape, with each of the three rings being essentially planar. The dihedral angles between the pyrazole ring and the two benzene rings are 72.28 (14) and 25.6 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015157/lh2046sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015157/lh2046Isup2.hkl
Contains datablock I

CCDC reference: 607275

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.073
  • wR factor = 0.209
  • Data-to-parameter ratio = 13.4

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 C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.09 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C11 ... 1.43 Ang.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 3 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 0 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.

4-Chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-(4- methylbenzylideneamino)-1H-pyrazole3-carbonitrile top
Crystal data top
C19H10Cl3F3N4F(000) = 920
Mr = 457.66Dx = 1.526 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1971 reflections
a = 17.678 (4) Åθ = 2.4–24.2°
b = 10.262 (2) ŵ = 0.50 mm1
c = 11.477 (3) ÅT = 298 K
β = 106.935 (4)°Block, colourless
V = 1991.8 (8) Å30.23 × 0.18 × 0.13 mm
Z = 4
Data collection top
Bruker APEX area-detector
diffractometer
3517 independent reflections
Radiation source: fine-focus sealed tube2685 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 2120
Tmin = 0.894, Tmax = 0.938k = 1210
10217 measured reflectionsl = 1013
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1002P)2 + 2.0911P]
where P = (Fo2 + 2Fc2)/3
3517 reflections(Δ/σ)max < 0.001
263 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = 0.34 e Å3
Special details top

Experimental. Spectroscopic analysis: IR (KBr, ν, cm-1): 2355, 1603, 1568, 1523, 1507, 1366, 1310, 895, 819; 1H NMR (C3D6O, δ, p.p.m.): 9.27 (s, 1H), 8.10 (s, 2H), 7.72 (d, 2H), 7.28 (d, 2H), 2.35 (s, 2H); 13C NMR (C3D6O, δ, p.p.m.): 167.8 (1 C), 147.3 (1 C), 145.8 (1 C), 136.5 (2 C), 135.9 (1 C), 134.6 (1 C), 127.4 (2 C), 126.5 (1 C), 126.4 (2 C), 126.3 (1 C), 125.5 (2 C),112.3 (1 C), 117.0 (1 C), 92.8 (1 C), 20.8 (1 C); 19F NMR (C3D6O, δ, p.p.m.): -63.85 (3 F)

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
Cl10.34538 (7)0.99685 (13)0.38252 (13)0.0764 (5)
Cl20.15596 (10)0.67988 (15)0.05018 (15)0.0969 (6)
Cl30.46062 (7)0.49069 (11)0.23005 (12)0.0681 (4)
F10.0036 (2)1.0837 (5)0.1610 (4)0.1283 (15)
F20.0078 (3)0.9552 (5)0.2949 (6)0.165 (2)
F30.0551 (2)1.1311 (5)0.3396 (5)0.1408 (19)
N10.3104 (2)0.7735 (3)0.2076 (3)0.0535 (9)
N20.3514 (2)0.8241 (4)0.1361 (3)0.0601 (10)
N30.5001 (3)0.7619 (6)0.0078 (5)0.0934 (16)
N40.2957 (2)0.5900 (3)0.3208 (3)0.0520 (9)
C10.0400 (3)1.0324 (5)0.2647 (6)0.0713 (14)
C20.1120 (3)0.9670 (4)0.2522 (4)0.0541 (11)
C30.1024 (3)0.8640 (5)0.1712 (5)0.0630 (12)
H30.05200.83660.12730.076*
C40.1680 (3)0.8028 (4)0.1566 (4)0.0572 (11)
C50.2435 (3)0.8407 (4)0.2224 (4)0.0502 (10)
C60.2523 (2)0.9442 (4)0.3020 (4)0.0523 (11)
C70.1871 (3)1.0087 (4)0.3172 (4)0.0532 (11)
H70.19351.07910.37020.064*
C80.4059 (3)0.7342 (4)0.1381 (4)0.0542 (11)
C90.3998 (3)0.6278 (4)0.2106 (4)0.0537 (11)
C100.3379 (2)0.6537 (4)0.2548 (4)0.0472 (10)
C110.4588 (3)0.7518 (5)0.0662 (4)0.0635 (13)
C120.3274 (3)0.5006 (4)0.3969 (4)0.0529 (11)
H120.38100.48330.41120.064*
C130.2831 (2)0.4248 (4)0.4618 (4)0.0470 (10)
C140.2039 (2)0.4484 (4)0.4461 (4)0.0494 (10)
H140.17870.51650.39630.059*
C150.1621 (3)0.3715 (4)0.5039 (4)0.0556 (11)
H150.10860.38770.49200.067*
C160.1986 (3)0.2703 (4)0.5797 (4)0.0558 (11)
C170.2768 (3)0.2486 (5)0.5955 (5)0.0699 (14)
H170.30210.18120.64620.084*
C180.3193 (3)0.3246 (5)0.5378 (4)0.0664 (13)
H180.37280.30820.55030.080*
C190.1512 (4)0.1854 (5)0.6405 (5)0.0805 (16)
H19A0.17070.09760.64580.121*
H19B0.09660.18680.59340.121*
H19C0.15630.21790.72090.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0508 (7)0.0814 (9)0.0891 (10)0.0010 (6)0.0078 (6)0.0153 (7)
Cl20.0985 (11)0.0762 (10)0.1033 (12)0.0012 (8)0.0094 (9)0.0363 (8)
Cl30.0648 (7)0.0625 (8)0.0906 (9)0.0282 (6)0.0441 (7)0.0249 (6)
F10.088 (2)0.154 (4)0.136 (3)0.055 (3)0.021 (2)0.018 (3)
F20.116 (3)0.121 (3)0.312 (7)0.019 (3)0.148 (4)0.052 (4)
F30.075 (2)0.164 (4)0.183 (4)0.018 (2)0.036 (3)0.089 (4)
N10.058 (2)0.051 (2)0.059 (2)0.0048 (17)0.0282 (18)0.0088 (17)
N20.069 (2)0.057 (2)0.062 (2)0.007 (2)0.031 (2)0.0067 (19)
N30.074 (3)0.123 (4)0.097 (4)0.021 (3)0.047 (3)0.003 (3)
N40.057 (2)0.047 (2)0.057 (2)0.0050 (17)0.0244 (18)0.0082 (17)
C10.053 (3)0.069 (3)0.095 (4)0.004 (3)0.026 (3)0.005 (3)
C20.055 (3)0.051 (3)0.060 (3)0.002 (2)0.021 (2)0.007 (2)
C30.048 (3)0.056 (3)0.081 (3)0.006 (2)0.012 (2)0.002 (3)
C40.063 (3)0.046 (2)0.061 (3)0.002 (2)0.016 (2)0.001 (2)
C50.055 (3)0.044 (2)0.054 (2)0.003 (2)0.021 (2)0.0106 (19)
C60.048 (2)0.048 (2)0.058 (3)0.001 (2)0.011 (2)0.006 (2)
C70.056 (3)0.050 (2)0.056 (3)0.000 (2)0.019 (2)0.002 (2)
C80.048 (2)0.058 (3)0.061 (3)0.003 (2)0.023 (2)0.001 (2)
C90.052 (2)0.057 (3)0.057 (3)0.006 (2)0.022 (2)0.006 (2)
C100.052 (2)0.046 (2)0.047 (2)0.0037 (19)0.019 (2)0.0063 (18)
C110.054 (3)0.077 (3)0.067 (3)0.013 (2)0.028 (2)0.003 (3)
C120.049 (2)0.055 (3)0.058 (3)0.004 (2)0.020 (2)0.003 (2)
C130.054 (2)0.045 (2)0.046 (2)0.0020 (19)0.0196 (19)0.0037 (18)
C140.052 (2)0.049 (2)0.049 (2)0.006 (2)0.018 (2)0.0042 (19)
C150.052 (2)0.063 (3)0.057 (3)0.002 (2)0.023 (2)0.002 (2)
C160.072 (3)0.048 (2)0.056 (3)0.000 (2)0.034 (2)0.001 (2)
C170.081 (3)0.061 (3)0.078 (3)0.020 (3)0.039 (3)0.029 (3)
C180.058 (3)0.073 (3)0.075 (3)0.015 (2)0.030 (3)0.023 (3)
C190.106 (4)0.064 (3)0.089 (4)0.008 (3)0.056 (4)0.008 (3)
Geometric parameters (Å, º) top
Cl1—C61.723 (4)C7—H70.9300
Cl2—C41.725 (5)C8—C91.396 (6)
Cl3—C91.745 (4)C8—C111.427 (6)
F1—C11.325 (7)C9—C101.360 (6)
F2—C11.278 (6)C12—C131.454 (6)
F3—C11.305 (6)C12—H120.9300
N1—N21.346 (5)C13—C181.378 (6)
N1—C101.374 (5)C13—C141.381 (6)
N1—C51.422 (5)C14—C151.375 (6)
N2—C81.329 (6)C14—H140.9300
N3—C111.131 (6)C15—C161.387 (6)
N4—C121.279 (5)C15—H150.9300
N4—C101.374 (5)C16—C171.360 (7)
C1—C21.482 (7)C16—C191.513 (6)
C2—C31.384 (7)C17—C181.379 (7)
C2—C71.388 (6)C17—H170.9300
C3—C41.372 (6)C18—H180.9300
C3—H30.9300C19—H19A0.9600
C4—C51.384 (6)C19—H19B0.9600
C5—C61.380 (6)C19—H19C0.9600
C6—C71.383 (6)
N2—N1—C10113.2 (3)C10—C9—Cl3130.0 (3)
N2—N1—C5120.0 (3)C8—C9—Cl3123.8 (3)
C10—N1—C5126.7 (3)C9—C10—N1105.0 (4)
C8—N2—N1103.8 (3)C9—C10—N4137.6 (4)
C12—N4—C10121.1 (4)N1—C10—N4117.1 (3)
F2—C1—F3109.1 (6)N3—C11—C8177.8 (6)
F2—C1—F1103.4 (5)N4—C12—C13122.6 (4)
F3—C1—F1103.7 (5)N4—C12—H12118.7
F2—C1—C2113.6 (5)C13—C12—H12118.7
F3—C1—C2113.6 (5)C18—C13—C14118.6 (4)
F1—C1—C2112.6 (5)C18—C13—C12120.3 (4)
C3—C2—C7120.5 (4)C14—C13—C12121.1 (4)
C3—C2—C1118.0 (4)C15—C14—C13120.2 (4)
C7—C2—C1121.5 (4)C15—C14—H14119.9
C4—C3—C2119.2 (4)C13—C14—H14119.9
C4—C3—H3120.4C14—C15—C16121.0 (4)
C2—C3—H3120.4C14—C15—H15119.5
C3—C4—C5121.3 (4)C16—C15—H15119.5
C3—C4—Cl2119.1 (4)C17—C16—C15118.3 (4)
C5—C4—Cl2119.5 (4)C17—C16—C19121.5 (4)
C6—C5—C4118.8 (4)C15—C16—C19120.1 (4)
C6—C5—N1121.0 (4)C16—C17—C18121.2 (4)
C4—C5—N1120.1 (4)C16—C17—H17119.4
C5—C6—C7121.0 (4)C18—C17—H17119.4
C5—C6—Cl1120.1 (3)C13—C18—C17120.6 (4)
C7—C6—Cl1118.9 (4)C13—C18—H18119.7
C6—C7—C2119.1 (4)C17—C18—H18119.7
C6—C7—H7120.5C16—C19—H19A109.5
C2—C7—H7120.5C16—C19—H19B109.5
N2—C8—C9111.9 (4)H19A—C19—H19B109.5
N2—C8—C11119.7 (4)C16—C19—H19C109.5
C9—C8—C11128.3 (4)H19A—C19—H19C109.5
C10—C9—C8106.2 (4)H19B—C19—H19C109.5
 

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