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This study of the title compound, C14H9F3N4O, is part of a series of structural investigations of cyclo­oxygenase-2 (COX-2) inhibitors containing 1,3-diaryl­pyrazole derivatives. The crystal structure is stabilized by inter­molecular N—H...O and C—H...F hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680504256X/at2001sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680504256X/at2001Isup2.hkl
Contains datablock I

CCDC reference: 298356

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.141
  • Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C14 H9 F3 N4 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

6-[3-Phenyl-5-(trifluoromethyl)pyrazol-1-yl]pyridazin-3(2H)-one top
Crystal data top
C14H9F3N4OZ = 2
Mr = 306.25F(000) = 312
Triclinic, P1Dx = 1.546 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 7.603 (2) ÅCell parameters from 25 reflections
b = 8.079 (2) Åθ = 4.1–74.2°
c = 11.202 (4) ŵ = 1.14 mm1
α = 82.97 (3)°T = 295 K
β = 74.84 (3)°Prism, colourless
γ = 84.95 (3)°0.40 × 0.40 × 0.30 mm
V = 658.0 (3) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
1979 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.014
Graphite monochromatorθmax = 74.2°, θmin = 4.1°
ω/2θ scansh = 99
Absorption correction: ψ scan
(North et al., 1968)
k = 410
Tmin = 0.658, Tmax = 0.726l = 1313
2839 measured reflections3 standard reflections every 120 min
2555 independent reflections intensity decay: none
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)] = 0.047Hydrogen site location: difference Fourier map
wR(F2) = 0.141All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.1019P)2 + 0.0709P]
where P = (Fo2 + 2Fc2)/3
2555 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.23 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2938 (3)0.4488 (2)1.13582 (18)0.0463 (4)
C20.1313 (3)0.3913 (2)1.1007 (2)0.0534 (5)
C30.1241 (3)0.2370 (3)1.0412 (2)0.0568 (5)
C40.2788 (3)0.1348 (2)1.01490 (19)0.0512 (5)
C50.4237 (3)0.6724 (2)1.27347 (19)0.0495 (4)
C60.5696 (3)0.5850 (3)1.3019 (2)0.0583 (5)
C70.3721 (3)0.8290 (2)1.3213 (2)0.0539 (5)
C80.2182 (3)0.8535 (2)1.27909 (18)0.0496 (4)
C90.1033 (3)0.9978 (2)1.31147 (19)0.0499 (5)
C100.1569 (3)1.1399 (3)1.3798 (2)0.0627 (6)
C110.0464 (4)1.2738 (3)1.4165 (3)0.0702 (7)
C120.1156 (4)1.2688 (3)1.3852 (2)0.0659 (6)
C130.1695 (3)1.1301 (3)1.3154 (2)0.0652 (6)
C140.0602 (3)0.9949 (3)1.2787 (2)0.0580 (5)
N10.4381 (2)0.36511 (19)1.11129 (17)0.0527 (4)
N20.4271 (2)0.2098 (2)1.05103 (18)0.0538 (4)
N30.3045 (2)0.60768 (18)1.20470 (15)0.0485 (4)
N40.1778 (2)0.71823 (19)1.20758 (16)0.0515 (4)
O10.2841 (2)0.01111 (18)0.96438 (16)0.0671 (5)
F10.6319 (2)0.67911 (18)1.39104 (15)0.0837 (5)
F20.5104 (2)0.43810 (16)1.34564 (14)0.0744 (4)
F30.71366 (17)0.55744 (18)1.20686 (15)0.0775 (4)
H10.031 (4)0.467 (3)1.117 (2)0.077 (7)*
H20.538 (4)0.148 (3)1.046 (2)0.079 (8)*
H30.026 (4)0.189 (4)1.020 (3)0.089 (9)*
H70.429 (3)0.899 (3)1.381 (2)0.073 (7)*
H100.265 (3)1.139 (3)1.400 (2)0.062 (6)*
H110.085 (4)1.362 (4)1.463 (3)0.098 (10)*
H120.191 (4)1.358 (4)1.409 (3)0.096 (9)*
H130.280 (3)1.126 (3)1.292 (2)0.060 (6)*
H140.100 (3)0.896 (3)1.233 (2)0.063 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0490 (10)0.0345 (9)0.0551 (10)0.0043 (7)0.0154 (8)0.0021 (7)
C20.0507 (10)0.0430 (10)0.0678 (12)0.0085 (8)0.0203 (9)0.0046 (9)
C30.0495 (11)0.0480 (11)0.0756 (14)0.0059 (8)0.0267 (10)0.0093 (10)
C40.0532 (11)0.0397 (10)0.0620 (11)0.0060 (8)0.0212 (9)0.0063 (8)
C50.0490 (10)0.0398 (9)0.0612 (11)0.0034 (7)0.0187 (8)0.0002 (8)
C60.0541 (11)0.0492 (11)0.0769 (14)0.0035 (9)0.0280 (10)0.0022 (10)
C70.0565 (11)0.0423 (10)0.0653 (12)0.0033 (8)0.0238 (10)0.0046 (9)
C80.0551 (11)0.0348 (9)0.0596 (11)0.0027 (7)0.0188 (9)0.0016 (8)
C90.0565 (11)0.0351 (9)0.0589 (11)0.0051 (8)0.0180 (9)0.0016 (8)
C100.0655 (14)0.0445 (11)0.0839 (15)0.0115 (9)0.0351 (12)0.0128 (10)
C110.0840 (16)0.0413 (11)0.0897 (17)0.0183 (10)0.0370 (14)0.0190 (11)
C120.0752 (15)0.0487 (12)0.0746 (14)0.0210 (11)0.0204 (12)0.0054 (10)
C130.0617 (13)0.0544 (12)0.0842 (16)0.0122 (10)0.0270 (12)0.0005 (11)
C140.0621 (12)0.0398 (10)0.0743 (13)0.0040 (9)0.0257 (10)0.0038 (9)
O10.0664 (9)0.0454 (8)0.0934 (11)0.0124 (7)0.0372 (8)0.0210 (7)
F10.0898 (10)0.0726 (9)0.1057 (11)0.0128 (8)0.0617 (9)0.0119 (8)
F20.0815 (9)0.0558 (8)0.0974 (10)0.0064 (6)0.0367 (8)0.0202 (7)
F30.0483 (7)0.0808 (10)0.1012 (10)0.0109 (6)0.0168 (7)0.0003 (8)
N10.0485 (9)0.0367 (8)0.0730 (11)0.0055 (6)0.0204 (8)0.0072 (7)
N20.0509 (9)0.0372 (8)0.0740 (11)0.0086 (7)0.0223 (8)0.0094 (7)
N30.0504 (9)0.0343 (8)0.0633 (10)0.0071 (6)0.0208 (7)0.0024 (7)
N40.0533 (9)0.0362 (8)0.0687 (10)0.0094 (7)0.0243 (8)0.0040 (7)
Geometric parameters (Å, º) top
O1—C41.243 (2)C3—C41.444 (3)
F2—C61.336 (3)C3—H30.88 (3)
N3—N41.362 (2)C8—C71.409 (3)
N3—C51.368 (2)C2—H10.99 (3)
N3—C11.422 (2)C7—C51.362 (3)
F3—C61.326 (3)C7—H70.99 (2)
N1—C11.290 (2)C14—C131.387 (3)
N1—N21.357 (2)C14—H140.96 (2)
N4—C81.336 (2)C5—C61.486 (3)
F1—C61.341 (2)C10—C111.385 (3)
N2—C41.363 (3)C10—H100.91 (2)
N2—H21.01 (3)C11—C121.362 (4)
C1—C21.416 (3)C11—H110.91 (3)
C9—C141.383 (3)C12—C131.381 (3)
C9—C101.392 (3)C12—H120.93 (3)
C9—C81.471 (3)C13—H130.94 (2)
C3—C21.344 (3)
N4—N3—C5111.44 (15)C5—C7—H7122.7 (15)
N4—N3—C1118.10 (15)C8—C7—H7130.6 (15)
C5—N3—C1130.45 (16)C13—C14—C9120.4 (2)
C1—N1—N2116.18 (16)C13—C14—H14120.3 (15)
C8—N4—N3105.40 (15)C9—C14—H14119.2 (15)
N1—N2—C4126.27 (16)C7—C5—N3106.53 (17)
N1—N2—H2110.8 (15)C7—C5—C6125.89 (19)
C4—N2—H2122.4 (15)N3—C5—C6127.31 (17)
N1—C1—C2124.50 (17)C9—C10—C11120.5 (2)
N1—C1—N3115.41 (16)C9—C10—H10117.3 (15)
C2—C1—N3120.08 (17)C11—C10—H10122.2 (15)
C14—C9—C10118.65 (19)F3—C6—F2107.08 (18)
C14—C9—C8121.75 (17)F3—C6—F1106.23 (18)
C10—C9—C8119.57 (18)F2—C6—F1106.37 (19)
C2—C3—C4120.13 (19)F3—C6—C5114.65 (19)
C2—C3—H3124.0 (19)F2—C6—C5113.01 (17)
C4—C3—H3115.8 (19)F1—C6—C5108.98 (17)
O1—C4—N2119.92 (18)C12—C11—C10120.4 (2)
O1—C4—C3125.26 (18)C12—C11—H11122 (2)
N2—C4—C3114.82 (17)C10—C11—H11117 (2)
N4—C8—C7110.35 (17)C11—C12—C13119.9 (2)
N4—C8—C9121.68 (17)C11—C12—H12121.5 (19)
C7—C8—C9127.85 (17)C13—C12—H12118.6 (19)
C3—C2—C1118.02 (19)C14—C13—C12120.1 (2)
C3—C2—H1122.4 (15)C14—C13—H13119.2 (15)
C1—C2—H1119.5 (15)C12—C13—H13120.7 (15)
C5—C7—C8106.27 (18)
C5—N3—N4—C80.1 (2)N4—C8—C7—C50.5 (2)
C1—N3—N4—C8179.13 (17)C9—C8—C7—C5175.5 (2)
C1—N1—N2—C40.3 (3)C10—C9—C14—C131.2 (4)
N2—N1—C1—C22.1 (3)C8—C9—C14—C13177.0 (2)
N2—N1—C1—N3176.82 (17)C8—C7—C5—N30.4 (2)
N4—N3—C1—N1164.22 (18)C8—C7—C5—C6174.1 (2)
C5—N3—C1—N116.8 (3)N4—N3—C5—C70.2 (2)
N4—N3—C1—C216.8 (3)C1—N3—C5—C7179.28 (19)
C5—N3—C1—C2162.3 (2)N4—N3—C5—C6174.14 (19)
N1—N2—C4—O1177.2 (2)C1—N3—C5—C64.9 (4)
N1—N2—C4—C32.3 (3)C14—C9—C10—C111.5 (4)
C2—C3—C4—O1177.4 (2)C8—C9—C10—C11176.8 (2)
C2—C3—C4—N22.1 (3)C7—C5—C6—F3113.4 (2)
N3—N4—C8—C70.3 (2)N3—C5—C6—F373.3 (3)
N3—N4—C8—C9175.91 (17)C7—C5—C6—F2123.5 (2)
C14—C9—C8—N45.7 (3)N3—C5—C6—F249.8 (3)
C10—C9—C8—N4176.1 (2)C7—C5—C6—F15.4 (3)
C14—C9—C8—C7169.8 (2)N3—C5—C6—F1167.9 (2)
C10—C9—C8—C78.4 (3)C9—C10—C11—C120.6 (4)
C4—C3—C2—C10.1 (4)C10—C11—C12—C130.6 (4)
N1—C1—C2—C32.2 (3)C9—C14—C13—C120.0 (4)
N3—C1—C2—C3176.7 (2)C11—C12—C13—C140.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i1.00 (3)1.79 (3)2.790 (2)172 (2)
C2—H1···F3ii0.99 (3)2.50 (3)3.418 (3)156 (2)
Symmetry codes: (i) x+1, y, z+2; (ii) x1, y, z.
 

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