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In the title compound, C24H18F3N3O2, the dihedral angles formed by the pyrazolone ring with one benzene and two phenyl rings are 26.18 (6), 74.42 (6) and 46.75 (8)°, respectively. The compound is in an enamine–keto form and its structure is stabilized by three intra­molecular (N—H...O, C—H...O and C—H...F) and two inter­molecular (C—H...O and C—H...F) hydrogen-bond inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029655/at2067sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029655/at2067Isup2.hkl
Contains datablock I

CCDC reference: 620523

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.049
  • wR factor = 0.125
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.67 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.60 Deg. C24' -O2 -C24 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2004); software used to prepare material for publication: CrystalStructure.

(4Z)-3-Methyl-1-phenyl-4-{(phenyl)[4-(trifluoromethoxy)anilino]methylene}- 1H-pyrazol-5(4H)-one top
Crystal data top
C24H18F3N3O2Z = 2
Mr = 437.41F(000) = 452
Triclinic, P1Dx = 1.420 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 8.0696 (9) ÅCell parameters from 2686 reflections
b = 11.0945 (12) Åθ = 1.7–27.9°
c = 13.1253 (14) ŵ = 0.11 mm1
α = 106.698 (4)°T = 113 K
β = 99.688 (5)°Platelet, yellow
γ = 108.459 (9)°0.32 × 0.20 × 0.10 mm
V = 1023.2 (2) Å3
Data collection top
Rigaku Saturn
diffractometer
4770 independent reflections
Radiation source: Rotating anode2854 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.040
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.7°
ω scansh = 910
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1412
Tmin = 0.966, Tmax = 0.989l = 1716
9409 measured reflections
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)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0558P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.003
4770 reflectionsΔρmax = 0.27 e Å3
332 parametersΔρmin = 0.28 e Å3
175 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.028 (4)
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*/UeqOcc. (<1)
O10.75299 (16)0.61087 (13)0.75314 (11)0.0270 (3)
N11.0507 (2)0.76483 (16)0.85706 (12)0.0234 (4)
N21.1526 (2)0.90516 (16)0.89128 (13)0.0260 (4)
N30.5576 (2)0.74522 (17)0.68609 (13)0.0255 (4)
C10.8722 (2)0.72936 (19)0.79899 (15)0.0230 (4)
C20.8595 (2)0.85739 (19)0.80125 (15)0.0231 (4)
C31.0399 (2)0.9593 (2)0.85964 (15)0.0248 (4)
C41.1115 (3)1.10967 (19)0.88521 (17)0.0315 (5)
H4A1.24441.14810.91590.047*
H4B1.05781.15230.93950.047*
H4C1.07941.12720.81700.047*
C51.1405 (2)0.67718 (19)0.87229 (15)0.0225 (4)
C61.3272 (2)0.7184 (2)0.88455 (15)0.0264 (4)
H61.39510.80560.88430.032*
C71.4128 (3)0.6309 (2)0.89710 (16)0.0304 (5)
H71.53960.65810.90450.036*
C81.3152 (3)0.5043 (2)0.89891 (16)0.0320 (5)
H81.37470.44480.90720.038*
C91.1305 (3)0.4651 (2)0.88854 (16)0.0330 (5)
H91.06340.37860.89030.040*
C101.0423 (3)0.5514 (2)0.87561 (16)0.0280 (4)
H100.91580.52440.86910.034*
C110.7013 (2)0.86304 (19)0.74477 (15)0.0230 (4)
C120.6887 (2)0.99317 (19)0.74178 (15)0.0222 (4)
C130.6850 (2)1.0887 (2)0.83605 (16)0.0262 (4)
H130.69371.07270.90370.031*
C140.6686 (2)1.2076 (2)0.83042 (16)0.0284 (5)
H140.66471.27270.89440.034*
C150.6576 (2)1.2319 (2)0.73190 (17)0.0289 (5)
H150.64801.31400.72880.035*
C160.6608 (2)1.1359 (2)0.63806 (16)0.0285 (5)
H160.65261.15210.57050.034*
C170.6759 (2)1.0167 (2)0.64273 (16)0.0259 (4)
H170.67750.95090.57830.031*
C180.3868 (2)0.72462 (19)0.61816 (15)0.0235 (4)
C190.2873 (2)0.8028 (2)0.65143 (15)0.0251 (4)
H190.33440.87460.72200.030*
C200.1192 (2)0.7767 (2)0.58221 (16)0.0264 (4)
H200.05070.82990.60480.032*
C210.0539 (2)0.6720 (2)0.48025 (15)0.0254 (4)
C220.1491 (2)0.5916 (2)0.44563 (16)0.0259 (4)
H220.10070.51910.37550.031*
C230.3160 (2)0.61886 (19)0.51503 (15)0.0243 (4)
H230.38340.56480.49210.029*
O20.11392 (18)0.63400 (15)0.40217 (12)0.0386 (4)
F10.26439 (18)0.7258 (2)0.50398 (12)0.0570 (6)0.921 (3)
F20.1170 (2)0.83808 (19)0.41867 (18)0.0663 (7)0.921 (3)
F30.3549 (3)0.6536 (3)0.3282 (2)0.0758 (9)0.921 (3)
C240.2077 (3)0.7120 (3)0.4127 (2)0.0391 (7)0.921 (3)
C24'0.187 (2)0.7195 (14)0.3866 (15)0.059 (5)0.079 (3)
F1'0.195 (3)0.807 (2)0.4780 (17)0.075 (5)0.079 (3)
F2'0.081 (3)0.7895 (19)0.3384 (17)0.073 (6)0.079 (3)
F3'0.356 (2)0.653 (3)0.318 (2)0.063 (7)0.079 (3)
H30.581 (3)0.671 (3)0.6833 (19)0.061 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0252 (7)0.0205 (8)0.0332 (8)0.0094 (6)0.0046 (6)0.0082 (6)
N10.0242 (8)0.0177 (8)0.0280 (9)0.0086 (7)0.0051 (7)0.0086 (7)
N20.0279 (8)0.0199 (9)0.0290 (9)0.0086 (7)0.0054 (7)0.0096 (7)
N30.0260 (8)0.0212 (9)0.0309 (9)0.0127 (7)0.0053 (7)0.0096 (7)
C10.0234 (9)0.0236 (11)0.0226 (10)0.0103 (8)0.0067 (8)0.0079 (8)
C20.0277 (9)0.0207 (10)0.0242 (10)0.0126 (8)0.0074 (8)0.0091 (8)
C30.0267 (10)0.0238 (11)0.0244 (10)0.0107 (9)0.0060 (8)0.0091 (8)
C40.0307 (10)0.0213 (11)0.0387 (12)0.0088 (9)0.0033 (9)0.0106 (9)
C50.0274 (10)0.0220 (10)0.0219 (9)0.0139 (9)0.0063 (8)0.0089 (8)
C60.0275 (10)0.0294 (11)0.0250 (10)0.0128 (9)0.0067 (8)0.0124 (9)
C70.0290 (10)0.0378 (13)0.0278 (11)0.0185 (10)0.0062 (8)0.0115 (9)
C80.0371 (11)0.0306 (12)0.0298 (11)0.0218 (10)0.0025 (9)0.0073 (9)
C90.0385 (11)0.0237 (11)0.0353 (12)0.0136 (10)0.0030 (9)0.0112 (9)
C100.0287 (10)0.0258 (11)0.0301 (11)0.0124 (9)0.0052 (8)0.0107 (9)
C110.0271 (9)0.0213 (10)0.0213 (10)0.0106 (8)0.0077 (8)0.0068 (8)
C120.0202 (9)0.0199 (10)0.0270 (10)0.0089 (8)0.0050 (7)0.0092 (8)
C130.0286 (10)0.0260 (11)0.0262 (10)0.0125 (9)0.0052 (8)0.0118 (8)
C140.0295 (10)0.0257 (11)0.0306 (11)0.0142 (9)0.0070 (8)0.0080 (9)
C150.0243 (10)0.0228 (11)0.0370 (12)0.0082 (9)0.0013 (8)0.0126 (9)
C160.0283 (10)0.0282 (11)0.0301 (11)0.0093 (9)0.0061 (8)0.0152 (9)
C170.0279 (10)0.0251 (11)0.0266 (10)0.0107 (9)0.0085 (8)0.0112 (9)
C180.0234 (9)0.0228 (10)0.0287 (10)0.0101 (8)0.0086 (8)0.0136 (8)
C190.0268 (10)0.0236 (11)0.0254 (10)0.0107 (8)0.0075 (8)0.0082 (8)
C200.0255 (10)0.0289 (11)0.0313 (11)0.0165 (9)0.0103 (8)0.0122 (9)
C210.0206 (9)0.0279 (11)0.0283 (10)0.0098 (8)0.0048 (8)0.0118 (9)
C220.0271 (9)0.0220 (11)0.0293 (11)0.0096 (8)0.0094 (8)0.0095 (8)
C230.0256 (9)0.0217 (10)0.0298 (10)0.0120 (8)0.0095 (8)0.0114 (8)
O20.0290 (8)0.0412 (10)0.0380 (9)0.0205 (7)0.0019 (6)0.0027 (7)
F10.0301 (8)0.0714 (14)0.0512 (10)0.0182 (8)0.0166 (7)0.0049 (9)
F20.0783 (12)0.0583 (13)0.0782 (15)0.0378 (11)0.0101 (10)0.0414 (11)
F30.0514 (12)0.1042 (18)0.0504 (13)0.0553 (12)0.0156 (10)0.0128 (12)
C240.0320 (12)0.0495 (16)0.0340 (14)0.0264 (12)0.0034 (10)0.0043 (12)
C24'0.056 (6)0.064 (6)0.052 (6)0.029 (5)0.003 (6)0.014 (6)
F1'0.072 (7)0.073 (7)0.073 (7)0.032 (6)0.003 (6)0.022 (6)
F2'0.076 (8)0.075 (9)0.060 (8)0.021 (7)0.012 (7)0.029 (7)
F3'0.059 (9)0.070 (9)0.055 (9)0.041 (7)0.006 (7)0.003 (7)
Geometric parameters (Å, º) top
O1—C11.251 (2)C13—C141.388 (3)
N1—C11.382 (2)C13—H130.9500
N1—N21.402 (2)C14—C151.389 (3)
N1—C51.421 (2)C14—H140.9500
N2—C31.313 (2)C15—C161.388 (3)
N3—C111.344 (2)C15—H150.9500
N3—C181.420 (2)C16—C171.383 (3)
N3—H30.90 (2)C16—H160.9500
C1—C21.448 (2)C17—H170.9500
C2—C111.394 (2)C18—C191.389 (2)
C2—C31.438 (3)C18—C231.392 (2)
C3—C41.494 (3)C19—C201.391 (2)
C4—H4A0.9800C19—H190.9500
C4—H4B0.9800C20—C211.378 (2)
C4—H4C0.9800C20—H200.9500
C5—C101.387 (3)C21—C221.382 (2)
C5—C61.394 (2)C21—O21.409 (2)
C6—C71.388 (3)C22—C231.381 (2)
C6—H60.9500C22—H220.9500
C7—C81.384 (3)C23—H230.9500
C7—H70.9500O2—C24'1.308 (6)
C8—C91.384 (3)O2—C241.312 (2)
C8—H80.9500F1—C241.338 (3)
C9—C101.392 (3)F2—C241.330 (3)
C9—H90.9500F3—C241.311 (3)
C10—H100.9500C24'—F2'1.333 (10)
C11—C121.490 (2)C24'—F1'1.334 (10)
C12—C131.390 (2)C24'—F3'1.337 (10)
C12—C171.392 (3)
C1—N1—N2111.85 (14)C14—C13—H13120.3
C1—N1—C5128.24 (16)C12—C13—H13120.3
N2—N1—C5119.42 (14)C13—C14—C15120.45 (18)
C3—N2—N1106.66 (15)C13—C14—H14119.8
C11—N3—C18128.61 (17)C15—C14—H14119.8
C11—N3—H3113.5 (15)C16—C15—C14119.82 (18)
C18—N3—H3117.3 (15)C16—C15—H15120.1
O1—C1—N1126.04 (17)C14—C15—H15120.1
O1—C1—C2129.19 (16)C17—C16—C15120.11 (18)
N1—C1—C2104.74 (15)C17—C16—H16119.9
C11—C2—C3132.47 (18)C15—C16—H16119.9
C11—C2—C1122.00 (17)C16—C17—C12119.99 (18)
C3—C2—C1105.20 (15)C16—C17—H17120.0
N2—C3—C2111.48 (17)C12—C17—H17120.0
N2—C3—C4118.65 (17)C19—C18—C23119.37 (16)
C2—C3—C4129.85 (16)C19—C18—N3122.90 (17)
C3—C4—H4A109.5C23—C18—N3117.71 (16)
C3—C4—H4B109.5C18—C19—C20120.48 (17)
H4A—C4—H4B109.5C18—C19—H19119.8
C3—C4—H4C109.5C20—C19—H19119.8
H4A—C4—H4C109.5C21—C20—C19118.65 (16)
H4B—C4—H4C109.5C21—C20—H20120.7
C10—C5—C6120.29 (17)C19—C20—H20120.7
C10—C5—N1119.86 (16)C20—C21—C22122.06 (16)
C6—C5—N1119.85 (17)C20—C21—O2124.74 (16)
C7—C6—C5119.35 (19)C22—C21—O2113.20 (16)
C7—C6—H6120.3C23—C22—C21118.70 (18)
C5—C6—H6120.3C23—C22—H22120.6
C8—C7—C6120.71 (18)C21—C22—H22120.6
C8—C7—H7119.6C22—C23—C18120.73 (16)
C6—C7—H7119.6C22—C23—H23119.6
C9—C8—C7119.56 (18)C18—C23—H23119.6
C9—C8—H8120.2C24'—O2—C2418.6 (8)
C7—C8—H8120.2C24'—O2—C21124.4 (8)
C8—C9—C10120.5 (2)C24—O2—C21121.31 (17)
C8—C9—H9119.7F3—C24—O2108.4 (2)
C10—C9—H9119.7F3—C24—F2109.2 (2)
C5—C10—C9119.55 (18)O2—C24—F2114.4 (2)
C5—C10—H10120.2F3—C24—F1106.4 (2)
C9—C10—H10120.2O2—C24—F1112.3 (2)
N3—C11—C2118.34 (17)F2—C24—F1105.9 (2)
N3—C11—C12118.86 (15)O2—C24'—F2'104.5 (10)
C2—C11—C12122.71 (16)O2—C24'—F1'115.7 (11)
C13—C12—C17120.22 (17)F2'—C24'—F1'109.1 (11)
C13—C12—C11120.49 (16)O2—C24'—F3'110.8 (13)
C17—C12—C11119.27 (16)F2'—C24'—F3'108.9 (12)
C14—C13—C12119.40 (17)F1'—C24'—F3'107.6 (12)
C1—N1—N2—C32.4 (2)C2—C11—C12—C17110.3 (2)
C5—N1—N2—C3175.02 (15)C17—C12—C13—C140.0 (3)
N2—N1—C1—O1175.70 (17)C11—C12—C13—C14178.38 (16)
C5—N1—C1—O13.9 (3)C12—C13—C14—C150.6 (3)
N2—N1—C1—C22.61 (19)C13—C14—C15—C160.8 (3)
C5—N1—C1—C2174.40 (16)C14—C15—C16—C170.4 (3)
O1—C1—C2—C112.3 (3)C15—C16—C17—C120.3 (3)
N1—C1—C2—C11175.93 (16)C13—C12—C17—C160.5 (3)
O1—C1—C2—C3176.45 (18)C11—C12—C17—C16178.86 (16)
N1—C1—C2—C31.80 (19)C11—N3—C18—C1946.2 (3)
N1—N2—C3—C21.1 (2)C11—N3—C18—C23135.4 (2)
N1—N2—C3—C4179.99 (16)C23—C18—C19—C200.5 (3)
C11—C2—C3—N2173.66 (19)N3—C18—C19—C20178.93 (18)
C1—C2—C3—N20.4 (2)C18—C19—C20—C210.1 (3)
C11—C2—C3—C45.0 (3)C19—C20—C21—C220.8 (3)
C1—C2—C3—C4178.27 (19)C19—C20—C21—O2179.75 (18)
C1—N1—C5—C1030.8 (3)C20—C21—C22—C231.0 (3)
N2—N1—C5—C10157.91 (17)O2—C21—C22—C23179.99 (17)
C1—N1—C5—C6149.57 (18)C21—C22—C23—C180.4 (3)
N2—N1—C5—C621.7 (2)C19—C18—C23—C220.4 (3)
C10—C5—C6—C71.7 (3)N3—C18—C23—C22178.86 (17)
N1—C5—C6—C7178.69 (16)C20—C21—O2—C24'34.3 (10)
C5—C6—C7—C80.8 (3)C22—C21—O2—C24'146.7 (10)
C6—C7—C8—C90.3 (3)C20—C21—O2—C2412.4 (3)
C7—C8—C9—C100.4 (3)C22—C21—O2—C24168.6 (2)
C6—C5—C10—C91.6 (3)C24'—O2—C24—F373 (2)
N1—C5—C10—C9178.85 (16)C21—O2—C24—F3178.8 (2)
C8—C9—C10—C50.5 (3)C24'—O2—C24—F249 (2)
C18—N3—C11—C2176.67 (17)C21—O2—C24—F256.7 (3)
C18—N3—C11—C120.0 (3)C24'—O2—C24—F1169 (3)
C3—C2—C11—N3171.82 (18)C21—O2—C24—F163.9 (3)
C1—C2—C11—N30.5 (3)C24—O2—C24'—F2'157 (3)
C3—C2—C11—C124.7 (3)C21—O2—C24'—F2'70.6 (14)
C1—C2—C11—C12177.03 (16)C24—O2—C24'—F1'37 (2)
N3—C11—C12—C13112.2 (2)C21—O2—C24'—F1'49.4 (16)
C2—C11—C12—C1371.3 (2)C24—O2—C24'—F3'86 (3)
N3—C11—C12—C1766.2 (2)C21—O2—C24'—F3'172.2 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O10.90 (2)1.92 (2)2.6938 (19)143 (2)
C20—H20···F10.952.382.906 (2)114
C10—H10···O10.952.432.965 (2)115
C15—H15···F3i0.952.533.178 (2)126
C22—H22···O1ii0.952.583.306 (2)133
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+1, z+1.
 

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