The title compound, C
23H
19N
3O
2, a condensation product of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone and
o-aminophenol, is a neutral tridentate ligand in enamine–keto form, due to a strong intramolecular N—H
O hydrogen bond. A pair of intermolecular O—H
O hydrogen bonds link molecules to give dimers.
Supporting information
CCDC reference: 202328
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.051
- wR factor = 0.141
- Data-to-parameter ratio = 11.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
THETM_01 Alert B The value of sine(theta_max)/wavelength is less than 0.575
Calculated sin(theta_max)/wavelength = 0.5565
Alert Level C:
PLAT_601 Alert C Structure Contains Solvent Accessible VOIDS of 66.00 A 3
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check
Ethanol solutions of 0.1 mol of PMBP and 0.1 mol of o-aminophenol were refluxed together for 4 h over a steam bath. The excess solvent was removed by evaporation and the concentrated solution was cooled in an ice bath with stirring. The title compound separated out as a cream powder, which was collected and dried in air. Bright-yellow single crystals, suitable for X-ray analysis, were obtained by slow cooling of a warmed ethanol solution, and were dried in a vacuum over CaCl2. The product is stable in air, and soluble in acetone and ethanol. Elemental analysis: calculated C 74.78, H 5.19, N 11.41%; found C 74.63, H 5.09, N 11.41%.
H atoms were placed geometrically and refined with riding-model constraints.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
4-[(2-Hydroxyphenylamino)phenylmethylene]-5-methyl-2-phenyl-2
H-pyrazol-3(4
H)- one
top
Crystal data top
C23H19N3O2 | F(000) = 388 |
Mr = 369.41 | Dx = 1.243 Mg m−3 |
Triclinic, P1 | Melting point = 239–240 K |
a = 7.267 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.150 (6) Å | Cell parameters from 2764 reflections |
c = 13.822 (8) Å | θ = 1.7–25.1° |
α = 111.794 (9)° | µ = 0.08 mm−1 |
β = 92.210 (11)° | T = 293 K |
γ = 105.987 (10)° | Prism, yellow |
V = 987.2 (10) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 2 | |
Data collection top
Bruker SMART 1000 CCD diffractometer | 1687 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 23.3°, θmin = 1.6° |
ω scans | h = −8→8 |
3405 measured reflections | k = −12→12 |
2830 independent reflections | l = −9→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.141 | w = 1/[σ2(Fo2) + (0.0697P)2 + 0.0157P] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.005 |
2830 reflections | Δρmax = 0.17 e Å−3 |
254 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.012 (3) |
Crystal data top
C23H19N3O2 | γ = 105.987 (10)° |
Mr = 369.41 | V = 987.2 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.267 (4) Å | Mo Kα radiation |
b = 11.150 (6) Å | µ = 0.08 mm−1 |
c = 13.822 (8) Å | T = 293 K |
α = 111.794 (9)° | 0.30 × 0.25 × 0.20 mm |
β = 92.210 (11)° | |
Data collection top
Bruker SMART 1000 CCD diffractometer | 1687 reflections with I > 2σ(I) |
3405 measured reflections | Rint = 0.024 |
2830 independent reflections | θmax = 23.3° |
Refinement top
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.17 e Å−3 |
2830 reflections | Δρmin = −0.19 e Å−3 |
254 parameters | |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.0194 (3) | 0.6134 (2) | 0.72338 (15) | 0.0479 (6) | |
O2 | 0.0988 (3) | 0.3694 (2) | 0.45905 (16) | 0.0596 (7) | |
H2 | 0.0857 | 0.3606 | 0.3974 | 0.089* | |
N1 | −0.2391 (4) | 0.4939 (3) | 0.89890 (19) | 0.0480 (7) | |
N2 | −0.1741 (4) | 0.5886 (3) | 0.85161 (18) | 0.0426 (7) | |
N3 | 0.1779 (4) | 0.4046 (3) | 0.65675 (19) | 0.0470 (7) | |
H3 | 0.1469 | 0.4714 | 0.6518 | 0.071* | |
C1 | −0.0494 (4) | 0.5515 (3) | 0.7818 (2) | 0.0386 (8) | |
C2 | −0.0200 (4) | 0.4326 (3) | 0.7901 (2) | 0.0390 (8) | |
C3 | −0.1449 (4) | 0.4038 (3) | 0.8632 (2) | 0.0436 (8) | |
C4 | −0.1862 (5) | 0.2880 (4) | 0.8989 (3) | 0.0592 (10) | |
H4A | −0.0810 | 0.3045 | 0.9512 | 0.089* | |
H4B | −0.2000 | 0.2047 | 0.8396 | 0.089* | |
H4C | −0.3040 | 0.2810 | 0.9286 | 0.089* | |
C5 | 0.0970 (4) | 0.3621 (3) | 0.7285 (2) | 0.0393 (8) | |
C11 | −0.2587 (5) | 0.6946 (3) | 0.8672 (2) | 0.0419 (8) | |
C12 | −0.1411 (5) | 0.8204 (4) | 0.8751 (3) | 0.0552 (9) | |
H12 | −0.0089 | 0.8360 | 0.8740 | 0.083* | |
C13 | −0.2220 (6) | 0.9233 (4) | 0.8844 (3) | 0.0640 (10) | |
H13 | −0.1433 | 1.0074 | 0.8893 | 0.096* | |
C14 | −0.4176 (6) | 0.9016 (4) | 0.8865 (3) | 0.0657 (11) | |
H14 | −0.4714 | 0.9698 | 0.8911 | 0.098* | |
C15 | −0.5333 (5) | 0.7775 (4) | 0.8818 (3) | 0.0659 (11) | |
H15 | −0.6647 | 0.7633 | 0.8852 | 0.099* | |
C16 | −0.4541 (5) | 0.6723 (3) | 0.8719 (2) | 0.0537 (9) | |
H16 | −0.5324 | 0.5889 | 0.8684 | 0.081* | |
C21 | 0.1298 (4) | 0.2383 (3) | 0.7368 (2) | 0.0403 (8) | |
C22 | 0.2330 (5) | 0.2475 (3) | 0.8276 (2) | 0.0510 (9) | |
H22 | 0.2823 | 0.3308 | 0.8847 | 0.077* | |
C23 | 0.2623 (5) | 0.1306 (4) | 0.8324 (3) | 0.0622 (10) | |
H23 | 0.3301 | 0.1362 | 0.8932 | 0.093* | |
C24 | 0.1905 (6) | 0.0069 (4) | 0.7469 (3) | 0.0704 (11) | |
H24 | 0.2132 | −0.0699 | 0.7499 | 0.106* | |
C25 | 0.0863 (7) | −0.0033 (4) | 0.6578 (3) | 0.0801 (13) | |
H25 | 0.0359 | −0.0872 | 0.6013 | 0.120* | |
C26 | 0.0556 (6) | 0.1127 (4) | 0.6519 (2) | 0.0655 (11) | |
H26 | −0.0143 | 0.1059 | 0.5913 | 0.098* | |
C31 | 0.3075 (4) | 0.3579 (3) | 0.5865 (2) | 0.0408 (8) | |
C32 | 0.2665 (4) | 0.3454 (3) | 0.4826 (2) | 0.0425 (8) | |
C33 | 0.3932 (5) | 0.3112 (3) | 0.4130 (2) | 0.0530 (9) | |
H33 | 0.3679 | 0.3041 | 0.3442 | 0.080* | |
C34 | 0.5586 (5) | 0.2874 (4) | 0.4453 (3) | 0.0663 (11) | |
H34 | 0.6425 | 0.2633 | 0.3977 | 0.099* | |
C35 | 0.5990 (5) | 0.2992 (4) | 0.5476 (3) | 0.0666 (11) | |
H35 | 0.7100 | 0.2836 | 0.5689 | 0.100* | |
C36 | 0.4734 (5) | 0.3344 (4) | 0.6184 (2) | 0.0576 (10) | |
H36 | 0.5002 | 0.3422 | 0.6872 | 0.086* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0564 (14) | 0.0540 (15) | 0.0510 (14) | 0.0276 (12) | 0.0160 (11) | 0.0320 (12) |
O2 | 0.0574 (16) | 0.0883 (19) | 0.0542 (14) | 0.0384 (14) | 0.0133 (11) | 0.0397 (13) |
N1 | 0.0530 (18) | 0.0510 (18) | 0.0490 (16) | 0.0209 (15) | 0.0140 (13) | 0.0258 (14) |
N2 | 0.0494 (17) | 0.0440 (17) | 0.0462 (15) | 0.0237 (14) | 0.0156 (13) | 0.0236 (13) |
N3 | 0.0565 (18) | 0.0543 (18) | 0.0475 (16) | 0.0322 (15) | 0.0138 (14) | 0.0277 (14) |
C1 | 0.0428 (19) | 0.041 (2) | 0.0360 (18) | 0.0173 (17) | 0.0048 (15) | 0.0170 (16) |
C2 | 0.0431 (19) | 0.043 (2) | 0.0394 (17) | 0.0188 (17) | 0.0089 (15) | 0.0214 (15) |
C3 | 0.046 (2) | 0.046 (2) | 0.0438 (19) | 0.0181 (18) | 0.0066 (16) | 0.0214 (16) |
C4 | 0.067 (3) | 0.059 (2) | 0.073 (2) | 0.029 (2) | 0.0233 (19) | 0.041 (2) |
C5 | 0.0400 (19) | 0.044 (2) | 0.0359 (17) | 0.0133 (16) | −0.0003 (15) | 0.0179 (15) |
C11 | 0.047 (2) | 0.047 (2) | 0.0396 (18) | 0.0227 (18) | 0.0087 (15) | 0.0198 (16) |
C12 | 0.054 (2) | 0.057 (2) | 0.067 (2) | 0.028 (2) | 0.0141 (18) | 0.0292 (19) |
C13 | 0.075 (3) | 0.053 (3) | 0.076 (3) | 0.030 (2) | 0.019 (2) | 0.031 (2) |
C14 | 0.085 (3) | 0.069 (3) | 0.064 (2) | 0.048 (3) | 0.019 (2) | 0.031 (2) |
C15 | 0.053 (2) | 0.088 (3) | 0.066 (2) | 0.041 (3) | 0.0129 (19) | 0.027 (2) |
C16 | 0.047 (2) | 0.059 (2) | 0.056 (2) | 0.021 (2) | 0.0078 (17) | 0.0191 (18) |
C21 | 0.0411 (19) | 0.042 (2) | 0.0396 (19) | 0.0169 (17) | 0.0048 (15) | 0.0159 (16) |
C22 | 0.055 (2) | 0.049 (2) | 0.054 (2) | 0.0219 (19) | 0.0020 (17) | 0.0218 (17) |
C23 | 0.067 (3) | 0.074 (3) | 0.071 (3) | 0.038 (2) | 0.015 (2) | 0.045 (2) |
C24 | 0.103 (3) | 0.053 (3) | 0.072 (3) | 0.039 (2) | 0.032 (2) | 0.031 (2) |
C25 | 0.128 (4) | 0.043 (2) | 0.057 (3) | 0.023 (3) | 0.008 (2) | 0.010 (2) |
C26 | 0.094 (3) | 0.051 (3) | 0.043 (2) | 0.019 (2) | −0.0025 (19) | 0.0142 (19) |
C31 | 0.0436 (19) | 0.040 (2) | 0.0427 (19) | 0.0215 (17) | 0.0102 (15) | 0.0149 (15) |
C32 | 0.044 (2) | 0.045 (2) | 0.0408 (19) | 0.0173 (17) | 0.0073 (15) | 0.0177 (15) |
C33 | 0.058 (2) | 0.060 (2) | 0.041 (2) | 0.021 (2) | 0.0100 (17) | 0.0171 (17) |
C34 | 0.063 (3) | 0.081 (3) | 0.056 (2) | 0.036 (2) | 0.0222 (19) | 0.018 (2) |
C35 | 0.056 (2) | 0.086 (3) | 0.062 (2) | 0.040 (2) | 0.0091 (19) | 0.021 (2) |
C36 | 0.059 (2) | 0.068 (3) | 0.049 (2) | 0.033 (2) | 0.0065 (18) | 0.0190 (18) |
Geometric parameters (Å, º) top
O1—C1 | 1.278 (3) | C14—H14 | 0.930 |
O2—C32 | 1.370 (3) | C15—C16 | 1.408 (5) |
O2—H2 | 0.820 | C15—H15 | 0.930 |
N1—C3 | 1.326 (4) | C16—H16 | 0.930 |
N1—N2 | 1.423 (3) | C21—C22 | 1.391 (4) |
N2—C1 | 1.379 (3) | C21—C26 | 1.393 (4) |
N2—C11 | 1.429 (4) | C22—C23 | 1.402 (4) |
N3—C5 | 1.340 (4) | C22—H22 | 0.930 |
N3—C31 | 1.437 (3) | C23—C24 | 1.385 (5) |
N3—H3 | 0.860 | C23—H23 | 0.930 |
C1—C2 | 1.444 (4) | C24—C25 | 1.370 (5) |
C2—C5 | 1.411 (4) | C24—H24 | 0.930 |
C2—C3 | 1.449 (4) | C25—C26 | 1.402 (5) |
C3—C4 | 1.507 (4) | C25—H25 | 0.930 |
C4—H4A | 0.960 | C26—H26 | 0.930 |
C4—H4B | 0.960 | C31—C36 | 1.392 (4) |
C4—H4C | 0.960 | C31—C32 | 1.402 (4) |
C5—C21 | 1.507 (4) | C32—C33 | 1.382 (4) |
C11—C16 | 1.381 (4) | C33—C34 | 1.392 (4) |
C11—C12 | 1.389 (5) | C33—H33 | 0.930 |
C12—C13 | 1.395 (4) | C34—C35 | 1.382 (5) |
C12—H12 | 0.930 | C34—H34 | 0.930 |
C13—C14 | 1.378 (5) | C35—C36 | 1.388 (4) |
C13—H13 | 0.930 | C35—H35 | 0.930 |
C14—C15 | 1.383 (5) | C36—H36 | 0.930 |
| | | |
C32—O2—H2 | 109.5 | C16—C15—H15 | 119.7 |
C3—N1—N2 | 105.6 (2) | C11—C16—C15 | 119.2 (3) |
C1—N2—N1 | 111.9 (2) | C11—C16—H16 | 120.4 |
C1—N2—C11 | 127.3 (2) | C15—C16—H16 | 120.4 |
N1—N2—C11 | 120.2 (2) | C22—C21—C26 | 119.6 (3) |
C5—N3—C31 | 131.2 (2) | C22—C21—C5 | 121.0 (3) |
C5—N3—H3 | 114.4 | C26—C21—C5 | 119.3 (3) |
C31—N3—H3 | 114.4 | C21—C22—C23 | 119.6 (3) |
O1—C1—N2 | 124.7 (3) | C21—C22—H22 | 120.2 |
O1—C1—C2 | 129.8 (3) | C23—C22—H22 | 120.2 |
N2—C1—C2 | 105.5 (2) | C24—C23—C22 | 120.2 (3) |
C5—C2—C1 | 122.7 (3) | C24—C23—H23 | 119.9 |
C5—C2—C3 | 132.1 (3) | C22—C23—H23 | 119.9 |
C1—C2—C3 | 105.0 (2) | C25—C24—C23 | 120.5 (3) |
N1—C3—C2 | 111.8 (3) | C25—C24—H24 | 119.8 |
N1—C3—C4 | 118.0 (3) | C23—C24—H24 | 119.8 |
C2—C3—C4 | 130.1 (3) | C24—C25—C26 | 120.0 (3) |
C3—C4—H4A | 109.5 | C24—C25—H25 | 120.0 |
C3—C4—H4B | 109.5 | C26—C25—H25 | 120.0 |
H4A—C4—H4B | 109.5 | C21—C26—C25 | 120.1 (3) |
C3—C4—H4C | 109.5 | C21—C26—H26 | 119.9 |
H4A—C4—H4C | 109.5 | C25—C26—H26 | 119.9 |
H4B—C4—H4C | 109.5 | C36—C31—C32 | 120.0 (3) |
N3—C5—C2 | 118.4 (3) | C36—C31—N3 | 123.6 (3) |
N3—C5—C21 | 118.3 (3) | C32—C31—N3 | 116.3 (2) |
C2—C5—C21 | 123.2 (3) | O2—C32—C33 | 125.1 (3) |
C16—C11—C12 | 120.3 (3) | O2—C32—C31 | 115.4 (2) |
C16—C11—N2 | 121.0 (3) | C33—C32—C31 | 119.5 (3) |
C12—C11—N2 | 118.6 (3) | C32—C33—C34 | 120.2 (3) |
C11—C12—C13 | 119.8 (3) | C32—C33—H33 | 119.9 |
C11—C12—H12 | 120.1 | C34—C33—H33 | 119.9 |
C13—C12—H12 | 120.1 | C35—C34—C33 | 120.4 (3) |
C14—C13—C12 | 120.6 (4) | C35—C34—H34 | 119.8 |
C14—C13—H13 | 119.7 | C33—C34—H34 | 119.8 |
C12—C13—H13 | 119.7 | C34—C35—C36 | 119.8 (3) |
C13—C14—C15 | 119.5 (3) | C34—C35—H35 | 120.1 |
C13—C14—H14 | 120.3 | C36—C35—H35 | 120.1 |
C15—C14—H14 | 120.3 | C35—C36—C31 | 120.1 (3) |
C14—C15—C16 | 120.7 (3) | C35—C36—H36 | 120.0 |
C14—C15—H15 | 119.7 | C31—C36—H36 | 120.0 |
| | | |
C3—N1—N2—C1 | 3.8 (3) | C13—C14—C15—C16 | −1.8 (5) |
C3—N1—N2—C11 | 175.3 (3) | C12—C11—C16—C15 | 1.6 (5) |
N1—N2—C1—O1 | 174.9 (3) | N2—C11—C16—C15 | −176.7 (3) |
C11—N2—C1—O1 | 4.2 (5) | C14—C15—C16—C11 | 0.2 (5) |
N1—N2—C1—C2 | −4.5 (3) | N3—C5—C21—C22 | 115.1 (3) |
C11—N2—C1—C2 | −175.2 (3) | C2—C5—C21—C22 | −67.2 (4) |
O1—C1—C2—C5 | −0.8 (5) | N3—C5—C21—C26 | −64.8 (4) |
N2—C1—C2—C5 | 178.6 (3) | C2—C5—C21—C26 | 113.0 (4) |
O1—C1—C2—C3 | −176.0 (3) | C26—C21—C22—C23 | 0.4 (5) |
N2—C1—C2—C3 | 3.3 (3) | C5—C21—C22—C23 | −179.5 (3) |
N2—N1—C3—C2 | −1.5 (3) | C21—C22—C23—C24 | 0.6 (5) |
N2—N1—C3—C4 | −179.1 (3) | C22—C23—C24—C25 | −1.6 (6) |
C5—C2—C3—N1 | −175.7 (3) | C23—C24—C25—C26 | 1.5 (6) |
C1—C2—C3—N1 | −1.1 (3) | C22—C21—C26—C25 | −0.5 (5) |
C5—C2—C3—C4 | 1.5 (6) | C5—C21—C26—C25 | 179.4 (3) |
C1—C2—C3—C4 | 176.2 (3) | C24—C25—C26—C21 | −0.5 (6) |
C31—N3—C5—C2 | 177.3 (3) | C5—N3—C31—C36 | −47.9 (5) |
C31—N3—C5—C21 | −4.8 (5) | C5—N3—C31—C32 | 136.5 (3) |
C1—C2—C5—N3 | −2.6 (4) | C36—C31—C32—O2 | 179.4 (3) |
C3—C2—C5—N3 | 171.2 (3) | N3—C31—C32—O2 | −4.8 (4) |
C1—C2—C5—C21 | 179.7 (3) | C36—C31—C32—C33 | −0.8 (5) |
C3—C2—C5—C21 | −6.5 (5) | N3—C31—C32—C33 | 175.0 (3) |
C1—N2—C11—C16 | 133.0 (3) | O2—C32—C33—C34 | −179.2 (3) |
N1—N2—C11—C16 | −37.0 (4) | C31—C32—C33—C34 | 1.0 (5) |
C1—N2—C11—C12 | −45.3 (4) | C32—C33—C34—C35 | −0.8 (6) |
N1—N2—C11—C12 | 144.7 (3) | C33—C34—C35—C36 | 0.3 (6) |
C16—C11—C12—C13 | −1.9 (5) | C34—C35—C36—C31 | −0.1 (6) |
N2—C11—C12—C13 | 176.4 (3) | C32—C31—C36—C35 | 0.3 (5) |
C11—C12—C13—C14 | 0.3 (5) | N3—C31—C36—C35 | −175.1 (3) |
C12—C13—C14—C15 | 1.5 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1 | 0.86 | 2.01 | 2.750 (3) | 143 |
O2—H2···O1i | 0.82 | 1.96 | 2.724 (3) | 155 |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data |
Chemical formula | C23H19N3O2 |
Mr | 369.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.267 (4), 11.150 (6), 13.822 (8) |
α, β, γ (°) | 111.794 (9), 92.210 (11), 105.987 (10) |
V (Å3) | 987.2 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
|
Data collection |
Diffractometer | Bruker SMART 1000 CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3405, 2830, 1687 |
Rint | 0.024 |
θmax (°) | 23.3 |
(sin θ/λ)max (Å−1) | 0.557 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.141, 0.98 |
No. of reflections | 2830 |
No. of parameters | 254 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.19 |
Selected geometric parameters (Å, º) topO1—C1 | 1.278 (3) | N3—C5 | 1.340 (4) |
N1—C3 | 1.326 (4) | C1—C2 | 1.444 (4) |
N1—N2 | 1.423 (3) | C2—C5 | 1.411 (4) |
N2—C1 | 1.379 (3) | C2—C3 | 1.449 (4) |
| | | |
C3—N1—N2 | 105.6 (2) | C1—C2—C3 | 105.0 (2) |
C1—N2—N1 | 111.9 (2) | N1—C3—C2 | 111.8 (3) |
N2—C1—C2 | 105.5 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1 | 0.86 | 2.01 | 2.750 (3) | 143 |
O2—H2···O1i | 0.82 | 1.96 | 2.724 (3) | 155 |
Symmetry code: (i) −x, −y+1, −z+1. |
A view of the molecular structure of the title compound, (I), is shown in Fig. 1. The compound was prepared from the reaction of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone (PMBP) and o-aminophenol, forming this tridentate ligand. In the pyrazole ring, the bond lengths C1—C2, C2—C3, C3—N1, N1—N2 and N2—C1 (Table 1) lie between classical single- and double-bond lengths. The bond angles within this ring deviate by up to 4° from the 108° angle of a regular pentagon.
The bond lengths O1—C1, C2—C5, C1—C2 and C5—N3 also lie between classical single- and double-bond lengths. Atoms O1, C1, C2, C5 and N3 are essentially coplanar, the largest deviation from the mean plane being 0.020 (2) Å for C5. The dihedral angle between this mean plane and that of the pyrazoline ring is 5.05 (3)°, indicating a high degree of conjugation and electron delocalization. The dihedral angles between the first mean plane and phenyl rings C11–C16, C21–C26 and C31–C36 are 45.91 (3), 113.79 (4) and 129.96 (4)°, respectively, because of steric hindrance effects. The C11—N2—N1—C3 torsion angle is −4.7 (3)°, different from the value of 16.7 (3)° in 3-(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenylpyrazol-4-ylmino)-4,4,4-trifluoro- 1-(2-thienyl)butane-1,2-dione (Wang et al., 2002). Small torsion angles for C1—C2—C5—N3 [−2.6 (4)°] and N3—C31—C32—O2 [−4.8 (4)°], show that atoms O1, N3 and O2 are in a cis conformation and can act as the coordinating atoms of a tridentate ligand.
A strong intramolecular N3—H3···O1 hydrogen bond is found (Table 2), resulting in an enamine–keto tautomeric form. Pairs of intermolecular O—H···O hydrogen bonds link molecules into centrosymmetric dimers, with the formation of a 14-membered ring (Fig. 2).