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The title compound, C20H14Cl2F3N5, is a tricyclic amide with an overall U-shape, each of the the three rings being planar. There are π–π interactions between the pyrazole ring and the benzene ring with the di­methyl­amine substituent.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004654/kp6044sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004654/kp6044Isup2.hkl
Contains datablock I

CCDC reference: 269805

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.066
  • wR factor = 0.186
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C20
Author Response: see _publ_section_exptl_refinement

Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT213_ALERT_2_C Atom F1 has ADP max/min Ratio ............. 3.20 prolat PLAT213_ALERT_2_C Atom F2 has ADP max/min Ratio ............. 3.70 prolat PLAT213_ALERT_2_C Atom F3 has ADP max/min Ratio ............. 3.50 prolat PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.67 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for F1 - C20 .. 5.66 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.56 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C12 - C13 ... 1.43 Ang.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 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 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: SHELXTL.

1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]- 5-[(4-dimethylaminobenzylidene)amino]-1H-pyrazole-3-carbonitrile top
Crystal data top
C20H14Cl2F3N5Z = 2
Mr = 452.26F(000) = 460
Triclinic, P1Dx = 1.464 Mg m3
Hall symbol: -P1Melting point = 456–458 K
a = 6.5692 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.365 (3) ÅCell parameters from 2322 reflections
c = 13.878 (3) Åθ = 2.8–24.7°
α = 67.312 (4)°µ = 0.36 mm1
β = 80.447 (4)°T = 298 K
γ = 86.740 (4)°Block, colorless
V = 1025.6 (4) Å30.42 × 0.29 × 0.23 mm
Data collection top
Bruker APEX area-detector
diffractometer
3638 independent reflections
Radiation source: fine-focus sealed tube2936 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
φ and ω scansθmax = 25.3°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 77
Tmin = 0.863, Tmax = 0.922k = 1414
5431 measured reflectionsl = 1615
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0899P)2 + 0.8389P]
where P = (Fo2 + 2Fc2)/3
3638 reflections(Δ/σ)max < 0.001
273 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.43 e Å3
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
Cl10.17763 (15)1.01711 (10)0.62395 (8)0.0776 (3)
Cl20.3709 (2)0.66437 (11)0.73789 (9)0.0986 (4)
F10.2047 (11)0.7678 (5)0.3594 (3)0.216 (3)
F20.2414 (10)0.6069 (3)0.4702 (3)0.227 (3)
F30.4448 (8)0.7388 (7)0.4263 (6)0.248 (3)
N10.7462 (4)0.5893 (3)1.1675 (2)0.0640 (8)
N20.0223 (4)0.8040 (2)0.88375 (18)0.0479 (6)
N30.1974 (4)0.8768 (2)0.75264 (19)0.0517 (6)
N40.3703 (4)0.9399 (3)0.7278 (2)0.0572 (7)
N50.7601 (5)1.0858 (3)0.8320 (3)0.0722 (9)
C10.8836 (6)0.5116 (4)1.1322 (3)0.0742 (10)
H1A0.82600.43381.16310.111*
H1B1.01540.51081.15370.111*
H1C0.90040.53861.05660.111*
C20.7723 (7)0.5953 (4)1.2671 (3)0.0871 (13)
H2A0.76150.67531.26120.131*
H2B0.90570.56571.28390.131*
H2C0.66710.54901.32200.131*
C30.5790 (5)0.6381 (3)1.1203 (2)0.0492 (7)
C40.4341 (5)0.7030 (3)1.1628 (2)0.0570 (8)
H40.45000.71001.22550.068*
C50.2705 (5)0.7560 (3)1.1132 (2)0.0540 (8)
H50.17800.79851.14290.065*
C60.2386 (4)0.7480 (3)1.0196 (2)0.0458 (7)
C70.3807 (5)0.6828 (3)0.9781 (2)0.0501 (7)
H70.36320.67530.91580.060*
C80.5447 (5)0.6298 (3)1.0265 (2)0.0520 (7)
H80.63590.58700.99640.062*
C90.0661 (4)0.8067 (3)0.9694 (2)0.0479 (7)
H90.01980.84971.00150.057*
C100.1495 (4)0.8675 (3)0.8479 (2)0.0453 (7)
C110.3009 (5)0.9267 (3)0.8875 (2)0.0497 (7)
H110.31420.93680.95130.060*
C120.4308 (5)0.9686 (3)0.8113 (2)0.0500 (7)
C130.6153 (5)1.0348 (3)0.8186 (3)0.0549 (8)
C140.0812 (5)0.8350 (3)0.6772 (2)0.0539 (8)
C150.0980 (5)0.8923 (3)0.6149 (2)0.0580 (8)
C160.2121 (6)0.8510 (4)0.5426 (3)0.0705 (10)
H160.33420.88830.50210.085*
C170.1420 (7)0.7544 (4)0.5317 (3)0.0782 (12)
C180.0373 (7)0.6981 (3)0.5907 (3)0.0760 (11)
H180.08380.63360.58150.091*
C190.1485 (6)0.7381 (3)0.6640 (3)0.0634 (9)
C200.2551 (11)0.7103 (5)0.4511 (4)0.121 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0658 (6)0.1047 (8)0.0728 (6)0.0015 (5)0.0118 (4)0.0446 (6)
Cl20.1089 (9)0.1047 (9)0.0861 (8)0.0259 (7)0.0308 (6)0.0555 (7)
F10.346 (8)0.204 (4)0.082 (3)0.091 (5)0.027 (3)0.076 (3)
F20.379 (8)0.097 (2)0.147 (3)0.027 (3)0.134 (4)0.057 (2)
F30.142 (4)0.380 (9)0.310 (7)0.018 (5)0.069 (5)0.273 (7)
N10.0603 (17)0.0737 (19)0.0635 (18)0.0192 (14)0.0175 (14)0.0315 (15)
N20.0478 (14)0.0580 (15)0.0401 (13)0.0042 (11)0.0040 (10)0.0227 (11)
N30.0487 (14)0.0712 (17)0.0403 (13)0.0170 (12)0.0073 (10)0.0290 (12)
N40.0538 (15)0.0758 (18)0.0484 (14)0.0194 (13)0.0108 (12)0.0322 (13)
N50.0612 (18)0.083 (2)0.086 (2)0.0205 (16)0.0112 (16)0.0498 (18)
C10.060 (2)0.078 (2)0.094 (3)0.0213 (19)0.019 (2)0.044 (2)
C20.096 (3)0.104 (3)0.076 (3)0.035 (3)0.041 (2)0.045 (2)
C30.0476 (16)0.0517 (17)0.0476 (16)0.0005 (13)0.0024 (13)0.0201 (14)
C40.0586 (19)0.077 (2)0.0461 (17)0.0121 (16)0.0110 (14)0.0353 (16)
C50.0543 (18)0.067 (2)0.0494 (17)0.0117 (15)0.0051 (14)0.0340 (15)
C60.0443 (15)0.0537 (17)0.0409 (15)0.0003 (13)0.0005 (12)0.0223 (13)
C70.0534 (17)0.0603 (18)0.0438 (16)0.0018 (14)0.0040 (13)0.0293 (14)
C80.0506 (17)0.0571 (18)0.0548 (18)0.0061 (14)0.0004 (14)0.0325 (15)
C90.0449 (16)0.0582 (18)0.0442 (16)0.0037 (13)0.0013 (12)0.0263 (14)
C100.0473 (16)0.0525 (16)0.0375 (14)0.0018 (13)0.0024 (12)0.0207 (13)
C110.0520 (17)0.0586 (18)0.0447 (16)0.0036 (14)0.0033 (13)0.0286 (14)
C120.0483 (17)0.0565 (18)0.0481 (16)0.0050 (13)0.0012 (13)0.0262 (14)
C130.0554 (19)0.0622 (19)0.0532 (18)0.0066 (16)0.0058 (14)0.0304 (16)
C140.0561 (19)0.071 (2)0.0378 (15)0.0221 (16)0.0094 (13)0.0261 (15)
C150.0519 (18)0.080 (2)0.0421 (16)0.0191 (16)0.0100 (14)0.0248 (16)
C160.065 (2)0.088 (3)0.0504 (19)0.0225 (19)0.0017 (16)0.0244 (19)
C170.103 (3)0.075 (2)0.0447 (19)0.029 (2)0.0087 (19)0.0220 (18)
C180.111 (3)0.063 (2)0.0492 (19)0.015 (2)0.006 (2)0.0267 (17)
C190.076 (2)0.070 (2)0.0429 (17)0.0110 (18)0.0012 (15)0.0266 (16)
C200.162 (6)0.100 (4)0.067 (3)0.037 (4)0.048 (3)0.025 (3)
Geometric parameters (Å, º) top
Cl1—C151.713 (4)C4—C51.370 (4)
Cl2—C191.718 (4)C4—H40.9300
F1—C201.285 (7)C5—C61.390 (4)
F2—C201.207 (7)C5—H50.9300
F3—C201.268 (8)C6—C71.395 (4)
N1—C31.363 (4)C6—C91.441 (4)
N1—C11.447 (4)C7—C81.364 (4)
N1—C21.451 (5)C7—H70.9300
N2—C91.281 (4)C8—H80.9300
N2—C101.386 (4)C9—H90.9300
N3—N41.357 (3)C10—C111.368 (4)
N3—C101.371 (4)C11—C121.394 (4)
N3—C141.433 (4)C11—H110.9300
N4—C121.332 (4)C12—C131.436 (4)
N5—C131.140 (4)C14—C151.386 (5)
C1—H1A0.9600C14—C191.387 (5)
C1—H1B0.9600C15—C161.390 (5)
C1—H1C0.9600C16—C171.374 (6)
C2—H2A0.9600C16—H160.9300
C2—H2B0.9600C17—C181.369 (6)
C2—H2C0.9600C17—C201.500 (5)
C3—C81.399 (4)C18—C191.383 (5)
C3—C41.411 (4)C18—H180.9300
C3—N1—C1121.8 (3)N2—C9—C6124.8 (3)
C3—N1—C2120.9 (3)N2—C9—H9117.6
C1—N1—C2116.3 (3)C6—C9—H9117.6
C9—N2—C10115.7 (2)C11—C10—N3105.7 (3)
N4—N3—C10113.3 (2)C11—C10—N2134.9 (3)
N4—N3—C14118.7 (2)N3—C10—N2119.4 (2)
C10—N3—C14127.8 (2)C10—C11—C12104.9 (3)
C12—N4—N3102.6 (2)C10—C11—H11127.6
N1—C1—H1A109.5C12—C11—H11127.6
N1—C1—H1B109.5N4—C12—C11113.5 (3)
H1A—C1—H1B109.5N4—C12—C13121.1 (3)
N1—C1—H1C109.5C11—C12—C13125.4 (3)
H1A—C1—H1C109.5N5—C13—C12174.9 (4)
H1B—C1—H1C109.5C15—C14—C19119.0 (3)
N1—C2—H2A109.5C15—C14—N3120.5 (3)
N1—C2—H2B109.5C19—C14—N3120.5 (3)
H2A—C2—H2B109.5C14—C15—C16120.5 (4)
N1—C2—H2C109.5C14—C15—Cl1120.2 (2)
H2A—C2—H2C109.5C16—C15—Cl1119.3 (3)
H2B—C2—H2C109.5C17—C16—C15119.1 (4)
N1—C3—C8122.4 (3)C17—C16—H16120.5
N1—C3—C4121.0 (3)C15—C16—H16120.5
C8—C3—C4116.6 (3)C18—C17—C16121.4 (3)
C5—C4—C3121.0 (3)C18—C17—C20117.8 (5)
C5—C4—H4119.5C16—C17—C20120.8 (5)
C3—C4—H4119.5C17—C18—C19119.4 (4)
C4—C5—C6121.9 (3)C17—C18—H18120.3
C4—C5—H5119.0C19—C18—H18120.3
C6—C5—H5119.0C18—C19—C14120.6 (4)
C5—C6—C7117.0 (3)C18—C19—Cl2118.3 (3)
C5—C6—C9119.9 (3)C14—C19—Cl2121.1 (2)
C7—C6—C9123.0 (3)F2—C20—F3108.3 (6)
C8—C7—C6121.7 (3)F2—C20—F1108.5 (7)
C8—C7—H7119.1F3—C20—F196.8 (5)
C6—C7—H7119.1F2—C20—C17117.2 (4)
C7—C8—C3121.7 (3)F3—C20—C17113.0 (6)
C7—C8—H8119.2F1—C20—C17111.2 (5)
C3—C8—H8119.2
 

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