organic compounds
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—HO and C—HF hydrogen-bonding interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680504256X/at2001sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680504256X/at2001Isup2.hkl |
CCDC reference: 298356
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
C14H9F3N4O | Z = 2 |
Mr = 306.25 | F(000) = 312 |
Triclinic, P1 | Dx = 1.546 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 7.603 (2) Å | Cell parameters from 25 reflections |
b = 8.079 (2) Å | θ = 4.1–74.2° |
c = 11.202 (4) Å | µ = 1.14 mm−1 |
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 tube | Rint = 0.014 |
Graphite monochromator | θmax = 74.2°, θmin = 4.1° |
ω/2θ scans | h = −9→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −4→10 |
Tmin = 0.658, Tmax = 0.726 | l = −13→13 |
2839 measured reflections | 3 standard reflections every 120 min |
2555 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.141 | All 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 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.2938 (3) | −0.4488 (2) | 1.13582 (18) | 0.0463 (4) | |
C2 | 0.1313 (3) | −0.3913 (2) | 1.1007 (2) | 0.0534 (5) | |
C3 | 0.1241 (3) | −0.2370 (3) | 1.0412 (2) | 0.0568 (5) | |
C4 | 0.2788 (3) | −0.1348 (2) | 1.01490 (19) | 0.0512 (5) | |
C5 | 0.4237 (3) | −0.6724 (2) | 1.27347 (19) | 0.0495 (4) | |
C6 | 0.5696 (3) | −0.5850 (3) | 1.3019 (2) | 0.0583 (5) | |
C7 | 0.3721 (3) | −0.8290 (2) | 1.3213 (2) | 0.0539 (5) | |
C8 | 0.2182 (3) | −0.8535 (2) | 1.27909 (18) | 0.0496 (4) | |
C9 | 0.1033 (3) | −0.9978 (2) | 1.31147 (19) | 0.0499 (5) | |
C10 | 0.1569 (3) | −1.1399 (3) | 1.3798 (2) | 0.0627 (6) | |
C11 | 0.0464 (4) | −1.2738 (3) | 1.4165 (3) | 0.0702 (7) | |
C12 | −0.1156 (4) | −1.2688 (3) | 1.3852 (2) | 0.0659 (6) | |
C13 | −0.1695 (3) | −1.1301 (3) | 1.3154 (2) | 0.0652 (6) | |
C14 | −0.0602 (3) | −0.9949 (3) | 1.2787 (2) | 0.0580 (5) | |
N1 | 0.4381 (2) | −0.36511 (19) | 1.11129 (17) | 0.0527 (4) | |
N2 | 0.4271 (2) | −0.2098 (2) | 1.05103 (18) | 0.0538 (4) | |
N3 | 0.3045 (2) | −0.60768 (18) | 1.20470 (15) | 0.0485 (4) | |
N4 | 0.1778 (2) | −0.71823 (19) | 1.20758 (16) | 0.0515 (4) | |
O1 | 0.2841 (2) | 0.01111 (18) | 0.96438 (16) | 0.0671 (5) | |
F1 | 0.6319 (2) | −0.67911 (18) | 1.39104 (15) | 0.0837 (5) | |
F2 | 0.5104 (2) | −0.43810 (16) | 1.34564 (14) | 0.0744 (4) | |
F3 | 0.71366 (17) | −0.55744 (18) | 1.20686 (15) | 0.0775 (4) | |
H1 | 0.031 (4) | −0.467 (3) | 1.117 (2) | 0.077 (7)* | |
H2 | 0.538 (4) | −0.148 (3) | 1.046 (2) | 0.079 (8)* | |
H3 | 0.026 (4) | −0.189 (4) | 1.020 (3) | 0.089 (9)* | |
H7 | 0.429 (3) | −0.899 (3) | 1.381 (2) | 0.073 (7)* | |
H10 | 0.265 (3) | −1.139 (3) | 1.400 (2) | 0.062 (6)* | |
H11 | 0.085 (4) | −1.362 (4) | 1.463 (3) | 0.098 (10)* | |
H12 | −0.191 (4) | −1.358 (4) | 1.409 (3) | 0.096 (9)* | |
H13 | −0.280 (3) | −1.126 (3) | 1.292 (2) | 0.060 (6)* | |
H14 | −0.100 (3) | −0.896 (3) | 1.233 (2) | 0.063 (6)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0490 (10) | 0.0345 (9) | 0.0551 (10) | −0.0043 (7) | −0.0154 (8) | 0.0021 (7) |
C2 | 0.0507 (10) | 0.0430 (10) | 0.0678 (12) | −0.0085 (8) | −0.0203 (9) | 0.0046 (9) |
C3 | 0.0495 (11) | 0.0480 (11) | 0.0756 (14) | −0.0059 (8) | −0.0267 (10) | 0.0093 (10) |
C4 | 0.0532 (11) | 0.0397 (10) | 0.0620 (11) | −0.0060 (8) | −0.0212 (9) | 0.0063 (8) |
C5 | 0.0490 (10) | 0.0398 (9) | 0.0612 (11) | −0.0034 (7) | −0.0187 (8) | 0.0002 (8) |
C6 | 0.0541 (11) | 0.0492 (11) | 0.0769 (14) | −0.0035 (9) | −0.0280 (10) | −0.0022 (10) |
C7 | 0.0565 (11) | 0.0423 (10) | 0.0653 (12) | −0.0033 (8) | −0.0238 (10) | 0.0046 (9) |
C8 | 0.0551 (11) | 0.0348 (9) | 0.0596 (11) | −0.0027 (7) | −0.0188 (9) | 0.0016 (8) |
C9 | 0.0565 (11) | 0.0351 (9) | 0.0589 (11) | −0.0051 (8) | −0.0180 (9) | 0.0016 (8) |
C10 | 0.0655 (14) | 0.0445 (11) | 0.0839 (15) | −0.0115 (9) | −0.0351 (12) | 0.0128 (10) |
C11 | 0.0840 (16) | 0.0413 (11) | 0.0897 (17) | −0.0183 (10) | −0.0370 (14) | 0.0190 (11) |
C12 | 0.0752 (15) | 0.0487 (12) | 0.0746 (14) | −0.0210 (11) | −0.0204 (12) | 0.0054 (10) |
C13 | 0.0617 (13) | 0.0544 (12) | 0.0842 (16) | −0.0122 (10) | −0.0270 (12) | −0.0005 (11) |
C14 | 0.0621 (12) | 0.0398 (10) | 0.0743 (13) | −0.0040 (9) | −0.0257 (10) | 0.0038 (9) |
O1 | 0.0664 (9) | 0.0454 (8) | 0.0934 (11) | −0.0124 (7) | −0.0372 (8) | 0.0210 (7) |
F1 | 0.0898 (10) | 0.0726 (9) | 0.1057 (11) | −0.0128 (8) | −0.0617 (9) | 0.0119 (8) |
F2 | 0.0815 (9) | 0.0558 (8) | 0.0974 (10) | −0.0064 (6) | −0.0367 (8) | −0.0202 (7) |
F3 | 0.0483 (7) | 0.0808 (10) | 0.1012 (10) | −0.0109 (6) | −0.0168 (7) | −0.0003 (8) |
N1 | 0.0485 (9) | 0.0367 (8) | 0.0730 (11) | −0.0055 (6) | −0.0204 (8) | 0.0072 (7) |
N2 | 0.0509 (9) | 0.0372 (8) | 0.0740 (11) | −0.0086 (7) | −0.0223 (8) | 0.0094 (7) |
N3 | 0.0504 (9) | 0.0343 (8) | 0.0633 (10) | −0.0071 (6) | −0.0208 (7) | 0.0024 (7) |
N4 | 0.0533 (9) | 0.0362 (8) | 0.0687 (10) | −0.0094 (7) | −0.0243 (8) | 0.0040 (7) |
Geometric parameters (Å, º) top
O1—C4 | 1.243 (2) | C3—C4 | 1.444 (3) |
F2—C6 | 1.336 (3) | C3—H3 | 0.88 (3) |
N3—N4 | 1.362 (2) | C8—C7 | 1.409 (3) |
N3—C5 | 1.368 (2) | C2—H1 | 0.99 (3) |
N3—C1 | 1.422 (2) | C7—C5 | 1.362 (3) |
F3—C6 | 1.326 (3) | C7—H7 | 0.99 (2) |
N1—C1 | 1.290 (2) | C14—C13 | 1.387 (3) |
N1—N2 | 1.357 (2) | C14—H14 | 0.96 (2) |
N4—C8 | 1.336 (2) | C5—C6 | 1.486 (3) |
F1—C6 | 1.341 (2) | C10—C11 | 1.385 (3) |
N2—C4 | 1.363 (3) | C10—H10 | 0.91 (2) |
N2—H2 | 1.01 (3) | C11—C12 | 1.362 (4) |
C1—C2 | 1.416 (3) | C11—H11 | 0.91 (3) |
C9—C14 | 1.383 (3) | C12—C13 | 1.381 (3) |
C9—C10 | 1.392 (3) | C12—H12 | 0.93 (3) |
C9—C8 | 1.471 (3) | C13—H13 | 0.94 (2) |
C3—C2 | 1.344 (3) | ||
N4—N3—C5 | 111.44 (15) | C5—C7—H7 | 122.7 (15) |
N4—N3—C1 | 118.10 (15) | C8—C7—H7 | 130.6 (15) |
C5—N3—C1 | 130.45 (16) | C13—C14—C9 | 120.4 (2) |
C1—N1—N2 | 116.18 (16) | C13—C14—H14 | 120.3 (15) |
C8—N4—N3 | 105.40 (15) | C9—C14—H14 | 119.2 (15) |
N1—N2—C4 | 126.27 (16) | C7—C5—N3 | 106.53 (17) |
N1—N2—H2 | 110.8 (15) | C7—C5—C6 | 125.89 (19) |
C4—N2—H2 | 122.4 (15) | N3—C5—C6 | 127.31 (17) |
N1—C1—C2 | 124.50 (17) | C9—C10—C11 | 120.5 (2) |
N1—C1—N3 | 115.41 (16) | C9—C10—H10 | 117.3 (15) |
C2—C1—N3 | 120.08 (17) | C11—C10—H10 | 122.2 (15) |
C14—C9—C10 | 118.65 (19) | F3—C6—F2 | 107.08 (18) |
C14—C9—C8 | 121.75 (17) | F3—C6—F1 | 106.23 (18) |
C10—C9—C8 | 119.57 (18) | F2—C6—F1 | 106.37 (19) |
C2—C3—C4 | 120.13 (19) | F3—C6—C5 | 114.65 (19) |
C2—C3—H3 | 124.0 (19) | F2—C6—C5 | 113.01 (17) |
C4—C3—H3 | 115.8 (19) | F1—C6—C5 | 108.98 (17) |
O1—C4—N2 | 119.92 (18) | C12—C11—C10 | 120.4 (2) |
O1—C4—C3 | 125.26 (18) | C12—C11—H11 | 122 (2) |
N2—C4—C3 | 114.82 (17) | C10—C11—H11 | 117 (2) |
N4—C8—C7 | 110.35 (17) | C11—C12—C13 | 119.9 (2) |
N4—C8—C9 | 121.68 (17) | C11—C12—H12 | 121.5 (19) |
C7—C8—C9 | 127.85 (17) | C13—C12—H12 | 118.6 (19) |
C3—C2—C1 | 118.02 (19) | C14—C13—C12 | 120.1 (2) |
C3—C2—H1 | 122.4 (15) | C14—C13—H13 | 119.2 (15) |
C1—C2—H1 | 119.5 (15) | C12—C13—H13 | 120.7 (15) |
C5—C7—C8 | 106.27 (18) | ||
C5—N3—N4—C8 | 0.1 (2) | N4—C8—C7—C5 | 0.5 (2) |
C1—N3—N4—C8 | −179.13 (17) | C9—C8—C7—C5 | −175.5 (2) |
C1—N1—N2—C4 | 0.3 (3) | C10—C9—C14—C13 | 1.2 (4) |
N2—N1—C1—C2 | 2.1 (3) | C8—C9—C14—C13 | −177.0 (2) |
N2—N1—C1—N3 | −176.82 (17) | C8—C7—C5—N3 | −0.4 (2) |
N4—N3—C1—N1 | −164.22 (18) | C8—C7—C5—C6 | 174.1 (2) |
C5—N3—C1—N1 | 16.8 (3) | N4—N3—C5—C7 | 0.2 (2) |
N4—N3—C1—C2 | 16.8 (3) | C1—N3—C5—C7 | 179.28 (19) |
C5—N3—C1—C2 | −162.3 (2) | N4—N3—C5—C6 | −174.14 (19) |
N1—N2—C4—O1 | 177.2 (2) | C1—N3—C5—C6 | 4.9 (4) |
N1—N2—C4—C3 | −2.3 (3) | C14—C9—C10—C11 | −1.5 (4) |
C2—C3—C4—O1 | −177.4 (2) | C8—C9—C10—C11 | 176.8 (2) |
C2—C3—C4—N2 | 2.1 (3) | C7—C5—C6—F3 | 113.4 (2) |
N3—N4—C8—C7 | −0.3 (2) | N3—C5—C6—F3 | −73.3 (3) |
N3—N4—C8—C9 | 175.91 (17) | C7—C5—C6—F2 | −123.5 (2) |
C14—C9—C8—N4 | −5.7 (3) | N3—C5—C6—F2 | 49.8 (3) |
C10—C9—C8—N4 | 176.1 (2) | C7—C5—C6—F1 | −5.4 (3) |
C14—C9—C8—C7 | 169.8 (2) | N3—C5—C6—F1 | 167.9 (2) |
C10—C9—C8—C7 | −8.4 (3) | C9—C10—C11—C12 | 0.6 (4) |
C4—C3—C2—C1 | −0.1 (4) | C10—C11—C12—C13 | 0.6 (4) |
N1—C1—C2—C3 | −2.2 (3) | C9—C14—C13—C12 | 0.0 (4) |
N3—C1—C2—C3 | 176.7 (2) | C11—C12—C13—C14 | −0.9 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 1.00 (3) | 1.79 (3) | 2.790 (2) | 172 (2) |
C2—H1···F3ii | 0.99 (3) | 2.50 (3) | 3.418 (3) | 156 (2) |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x−1, y, z. |