Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028711/at2325sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028711/at2325Isup2.hkl |
CCDC reference: 654965
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.133
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C18 - C19 .. 7.43 su
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Guo et al. (2006); Manna et al. (2002); Wiley et al. (1958).
1-(p-Methylphenyl)-3-(p-fluorophenyl)-2-propenyl-1-ketone (0.02 mol) and phenylhydrazine (0.02 mol) were mixed in 99.5% acetic acid (40 ml) and stirred in refluxing for 6 h, then the mixture was poured into ice-water to afford yellow solids·The solids were filtrated and washed with water until the pH of solution is about to 7.0. Finally, the solid crystals were dry under room temperature. Single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from EtOH at room temperature.
H atoms were fixed geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.96 Å and with Uiso(H) = 1.2Ueq or1.5Ueq of the parent atoms.
Pyrazolines are important and useful five-membered heterocyclic compounds. 1-Acetyl-3,5-diaryl-2-pyrazolines have been found to inhibit the monoamine oxidases (Manna et al., 2002). 1,3,5-Triaryl-2-pyrazolines were also used as scintillation solutes (Wiley et al., 1958). Here, we report the crystal structure of the title compound (I).
In the structure of (I) (Fig. 1), the values of the bond lengths and bond angles arel in the normal range (Guo et al., 2006). The mean plane of pyrazolinyl ring forms a dihedral angle of 18.52 (10)° with the phenyl ring, 71.69 (10)° with the fluorophenyl ring and 4.82 (10)° with the p-tolyl ring.
For related literature, see: Guo et al. (2006); Manna et al. (2002); Wiley et al. (1958).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level. |
C22H19FN2 | F(000) = 696 |
Mr = 330.39 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2776 reflections |
a = 14.854 (3) Å | θ = 2.3–24.0° |
b = 11.429 (2) Å | µ = 0.08 mm−1 |
c = 10.833 (2) Å | T = 298 K |
β = 109.090 (3)° | Block, yellow |
V = 1738.0 (6) Å3 | 0.50 × 0.45 × 0.10 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2155 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
φ and ω scans | h = −17→16 |
7135 measured reflections | k = −12→13 |
3066 independent reflections | l = −11→12 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0747P)2 + 0.1146P] where P = (Fo2 + 2Fc2)/3 |
3066 reflections | (Δ/σ)max = 0.003 |
227 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C22H19FN2 | V = 1738.0 (6) Å3 |
Mr = 330.39 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.854 (3) Å | µ = 0.08 mm−1 |
b = 11.429 (2) Å | T = 298 K |
c = 10.833 (2) Å | 0.50 × 0.45 × 0.10 mm |
β = 109.090 (3)° |
Bruker SMART CCD area-detector diffractometer | 2155 reflections with I > 2σ(I) |
7135 measured reflections | Rint = 0.020 |
3066 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.16 e Å−3 |
3066 reflections | Δρmin = −0.19 e Å−3 |
227 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.84586 (13) | 1.01263 (17) | −0.0443 (2) | 0.0773 (5) | |
H1 | 0.8430 | 0.9388 | −0.0814 | 0.093* | |
C2 | 0.90293 (14) | 1.09809 (18) | −0.07041 (19) | 0.0812 (5) | |
H2 | 0.9379 | 1.0814 | −0.1255 | 0.097* | |
C3 | 0.90851 (13) | 1.20709 (18) | −0.0161 (2) | 0.0848 (6) | |
H3 | 0.9460 | 1.2650 | −0.0351 | 0.102* | |
C4 | 0.85805 (13) | 1.22952 (17) | 0.0669 (2) | 0.0845 (6) | |
H4 | 0.8625 | 1.3029 | 0.1055 | 0.101* | |
C5 | 0.80102 (12) | 1.14601 (16) | 0.09424 (19) | 0.0739 (5) | |
H5 | 0.7677 | 1.1628 | 0.1514 | 0.089* | |
C6 | 0.79317 (12) | 1.03656 (15) | 0.03659 (17) | 0.0650 (4) | |
C7 | 0.70449 (13) | 0.84353 (15) | −0.01505 (18) | 0.0730 (5) | |
H7 | 0.6890 | 0.8604 | −0.1084 | 0.088* | |
C8 | 0.78013 (12) | 0.75006 (14) | 0.02456 (16) | 0.0616 (4) | |
C9 | 0.77887 (13) | 0.65943 (16) | −0.06012 (17) | 0.0711 (5) | |
H9 | 0.7329 | 0.6593 | −0.1426 | 0.085* | |
C10 | 0.84354 (14) | 0.56954 (17) | −0.0260 (2) | 0.0791 (5) | |
H10 | 0.8420 | 0.5090 | −0.0840 | 0.095* | |
C11 | 0.90948 (13) | 0.57141 (17) | 0.0943 (2) | 0.0755 (5) | |
C12 | 0.91423 (13) | 0.65768 (19) | 0.18137 (19) | 0.0817 (6) | |
H12 | 0.9604 | 0.6563 | 0.2636 | 0.098* | |
C13 | 0.84913 (14) | 0.74803 (17) | 0.14589 (17) | 0.0756 (5) | |
H13 | 0.8519 | 0.8083 | 0.2047 | 0.091* | |
C14 | 0.61277 (13) | 0.81138 (17) | 0.0143 (2) | 0.0825 (6) | |
H14A | 0.5578 | 0.8123 | −0.0647 | 0.099* | |
H14B | 0.6180 | 0.7348 | 0.0545 | 0.099* | |
C15 | 0.60609 (11) | 0.90527 (14) | 0.10650 (16) | 0.0612 (4) | |
C16 | 0.53417 (11) | 0.91201 (14) | 0.17113 (16) | 0.0617 (4) | |
C17 | 0.46009 (12) | 0.83265 (16) | 0.14551 (19) | 0.0753 (5) | |
H17 | 0.4552 | 0.7736 | 0.0846 | 0.090* | |
C18 | 0.39311 (12) | 0.83949 (18) | 0.2089 (2) | 0.0812 (6) | |
H18 | 0.3444 | 0.7844 | 0.1900 | 0.097* | |
C19 | 0.39667 (12) | 0.92547 (16) | 0.29887 (19) | 0.0737 (5) | |
C20 | 0.32370 (13) | 0.9332 (2) | 0.3669 (2) | 0.0968 (7) | |
H20A | 0.2669 | 0.8930 | 0.3163 | 0.145* | |
H20B | 0.3091 | 1.0138 | 0.3764 | 0.145* | |
H20C | 0.3484 | 0.8976 | 0.4516 | 0.145* | |
C21 | 0.47016 (14) | 1.00439 (18) | 0.3234 (2) | 0.0862 (6) | |
H21 | 0.4746 | 1.0637 | 0.3838 | 0.103* | |
C22 | 0.53736 (13) | 0.99869 (17) | 0.2615 (2) | 0.0810 (6) | |
H22 | 0.5859 | 1.0541 | 0.2808 | 0.097* | |
F1 | 0.97450 (8) | 0.48320 (11) | 0.13006 (15) | 0.1102 (5) | |
N1 | 0.67233 (10) | 0.98251 (12) | 0.12690 (13) | 0.0657 (4) | |
N2 | 0.73301 (11) | 0.95237 (12) | 0.06048 (16) | 0.0777 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0876 (12) | 0.0718 (11) | 0.0851 (13) | 0.0018 (9) | 0.0454 (11) | 0.0045 (10) |
C2 | 0.0812 (12) | 0.0913 (14) | 0.0851 (13) | 0.0026 (10) | 0.0462 (10) | 0.0124 (11) |
C3 | 0.0767 (11) | 0.0812 (13) | 0.1082 (16) | −0.0091 (10) | 0.0461 (11) | 0.0126 (12) |
C4 | 0.0788 (12) | 0.0689 (11) | 0.1175 (16) | −0.0094 (9) | 0.0480 (12) | −0.0024 (11) |
C5 | 0.0719 (10) | 0.0672 (11) | 0.0941 (13) | −0.0009 (9) | 0.0430 (10) | 0.0006 (10) |
C6 | 0.0659 (9) | 0.0604 (10) | 0.0760 (11) | 0.0025 (8) | 0.0331 (9) | 0.0074 (8) |
C7 | 0.0870 (11) | 0.0666 (11) | 0.0736 (11) | −0.0032 (9) | 0.0376 (9) | −0.0034 (9) |
C8 | 0.0734 (10) | 0.0604 (9) | 0.0608 (10) | −0.0114 (8) | 0.0354 (9) | −0.0045 (8) |
C9 | 0.0782 (11) | 0.0760 (11) | 0.0635 (11) | −0.0098 (10) | 0.0293 (9) | −0.0112 (9) |
C10 | 0.0902 (13) | 0.0680 (12) | 0.0921 (14) | −0.0091 (10) | 0.0476 (12) | −0.0156 (10) |
C11 | 0.0734 (11) | 0.0673 (11) | 0.0992 (15) | −0.0039 (9) | 0.0467 (11) | 0.0090 (11) |
C12 | 0.0800 (12) | 0.0912 (14) | 0.0733 (12) | −0.0115 (11) | 0.0242 (10) | 0.0079 (11) |
C13 | 0.0938 (12) | 0.0746 (12) | 0.0628 (11) | −0.0103 (11) | 0.0315 (10) | −0.0103 (9) |
C14 | 0.0778 (11) | 0.0760 (12) | 0.0999 (14) | −0.0071 (9) | 0.0377 (10) | −0.0111 (11) |
C15 | 0.0616 (9) | 0.0561 (9) | 0.0644 (10) | 0.0025 (8) | 0.0187 (8) | 0.0083 (8) |
C16 | 0.0553 (9) | 0.0582 (9) | 0.0702 (11) | 0.0039 (7) | 0.0187 (8) | 0.0115 (8) |
C17 | 0.0630 (10) | 0.0696 (11) | 0.0913 (13) | −0.0031 (9) | 0.0225 (9) | −0.0051 (10) |
C18 | 0.0544 (9) | 0.0796 (13) | 0.1092 (15) | −0.0072 (9) | 0.0261 (10) | 0.0081 (12) |
C19 | 0.0603 (10) | 0.0727 (11) | 0.0917 (13) | 0.0054 (9) | 0.0297 (9) | 0.0128 (10) |
C20 | 0.0713 (12) | 0.1072 (16) | 0.1243 (18) | −0.0014 (11) | 0.0491 (12) | 0.0124 (13) |
C21 | 0.0844 (12) | 0.0781 (12) | 0.1126 (16) | −0.0115 (10) | 0.0550 (12) | −0.0112 (11) |
C22 | 0.0751 (11) | 0.0708 (12) | 0.1084 (15) | −0.0156 (9) | 0.0454 (11) | −0.0075 (11) |
F1 | 0.0939 (8) | 0.0929 (8) | 0.1555 (12) | 0.0150 (7) | 0.0567 (8) | 0.0225 (8) |
N1 | 0.0708 (9) | 0.0589 (8) | 0.0762 (9) | 0.0022 (7) | 0.0361 (7) | 0.0072 (7) |
N2 | 0.0917 (10) | 0.0588 (8) | 0.1033 (12) | −0.0085 (7) | 0.0600 (9) | −0.0090 (8) |
C1—C6 | 1.380 (2) | C12—C13 | 1.381 (3) |
C1—C2 | 1.382 (3) | C12—H12 | 0.9300 |
C1—H1 | 0.9300 | C13—H13 | 0.9300 |
C2—C3 | 1.369 (3) | C14—C15 | 1.492 (3) |
C2—H2 | 0.9300 | C14—H14A | 0.9700 |
C3—C4 | 1.369 (3) | C14—H14B | 0.9700 |
C3—H3 | 0.9300 | C15—N1 | 1.2862 (19) |
C4—C5 | 1.371 (2) | C15—C16 | 1.458 (2) |
C4—H4 | 0.9300 | C16—C17 | 1.382 (2) |
C5—C6 | 1.386 (2) | C16—C22 | 1.383 (3) |
C5—H5 | 0.9300 | C17—C18 | 1.383 (3) |
C6—N2 | 1.394 (2) | C17—H17 | 0.9300 |
C7—N2 | 1.473 (2) | C18—C19 | 1.373 (3) |
C7—C8 | 1.507 (2) | C18—H18 | 0.9300 |
C7—C14 | 1.541 (2) | C19—C21 | 1.373 (3) |
C7—H7 | 0.9800 | C19—C20 | 1.500 (3) |
C8—C13 | 1.377 (2) | C20—H20A | 0.9600 |
C8—C9 | 1.380 (2) | C20—H20B | 0.9600 |
C9—C10 | 1.372 (3) | C20—H20C | 0.9600 |
C9—H9 | 0.9300 | C21—C22 | 1.373 (3) |
C10—C11 | 1.350 (3) | C21—H21 | 0.9300 |
C10—H10 | 0.9300 | C22—H22 | 0.9300 |
C11—C12 | 1.350 (3) | N1—N2 | 1.3686 (19) |
C11—F1 | 1.362 (2) | ||
C6—C1—C2 | 120.21 (18) | C8—C13—H13 | 119.6 |
C6—C1—H1 | 119.9 | C12—C13—H13 | 119.6 |
C2—C1—H1 | 119.9 | C15—C14—C7 | 102.92 (14) |
C3—C2—C1 | 120.67 (18) | C15—C14—H14A | 111.2 |
C3—C2—H2 | 119.7 | C7—C14—H14A | 111.2 |
C1—C2—H2 | 119.7 | C15—C14—H14B | 111.2 |
C2—C3—C4 | 118.92 (18) | C7—C14—H14B | 111.2 |
C2—C3—H3 | 120.5 | H14A—C14—H14B | 109.1 |
C4—C3—H3 | 120.5 | N1—C15—C16 | 121.38 (15) |
C3—C4—C5 | 121.39 (19) | N1—C15—C14 | 113.20 (15) |
C3—C4—H4 | 119.3 | C16—C15—C14 | 125.41 (15) |
C5—C4—H4 | 119.3 | C17—C16—C22 | 116.93 (16) |
C4—C5—C6 | 119.85 (17) | C17—C16—C15 | 121.94 (16) |
C4—C5—H5 | 120.1 | C22—C16—C15 | 121.14 (15) |
C6—C5—H5 | 120.1 | C16—C17—C18 | 121.18 (18) |
C1—C6—C5 | 118.91 (16) | C16—C17—H17 | 119.4 |
C1—C6—N2 | 120.82 (16) | C18—C17—H17 | 119.4 |
C5—C6—N2 | 120.27 (16) | C19—C18—C17 | 121.72 (17) |
N2—C7—C8 | 112.84 (15) | C19—C18—H18 | 119.1 |
N2—C7—C14 | 101.54 (14) | C17—C18—H18 | 119.1 |
C8—C7—C14 | 113.54 (15) | C18—C19—C21 | 116.80 (17) |
N2—C7—H7 | 109.6 | C18—C19—C20 | 121.65 (17) |
C8—C7—H7 | 109.6 | C21—C19—C20 | 121.55 (19) |
C14—C7—H7 | 109.6 | C19—C20—H20A | 109.5 |
C13—C8—C9 | 117.76 (17) | C19—C20—H20B | 109.5 |
C13—C8—C7 | 122.44 (16) | H20A—C20—H20B | 109.5 |
C9—C8—C7 | 119.74 (16) | C19—C20—H20C | 109.5 |
C10—C9—C8 | 121.78 (17) | H20A—C20—H20C | 109.5 |
C10—C9—H9 | 119.1 | H20B—C20—H20C | 109.5 |
C8—C9—H9 | 119.1 | C22—C21—C19 | 122.22 (19) |
C11—C10—C9 | 118.13 (18) | C22—C21—H21 | 118.9 |
C11—C10—H10 | 120.9 | C19—C21—H21 | 118.9 |
C9—C10—H10 | 120.9 | C21—C22—C16 | 121.15 (17) |
C12—C11—C10 | 122.76 (19) | C21—C22—H22 | 119.4 |
C12—C11—F1 | 118.17 (19) | C16—C22—H22 | 119.4 |
C10—C11—F1 | 119.07 (19) | C15—N1—N2 | 109.60 (14) |
C11—C12—C13 | 118.69 (18) | N1—N2—C6 | 119.76 (14) |
C11—C12—H12 | 120.7 | N1—N2—C7 | 112.66 (13) |
C13—C12—H12 | 120.7 | C6—N2—C7 | 124.43 (15) |
C8—C13—C12 | 120.87 (18) | ||
C6—C1—C2—C3 | 0.4 (3) | N1—C15—C16—C17 | 176.97 (15) |
C1—C2—C3—C4 | 1.3 (3) | C14—C15—C16—C17 | −4.0 (3) |
C2—C3—C4—C5 | −1.3 (3) | N1—C15—C16—C22 | −3.2 (2) |
C3—C4—C5—C6 | −0.5 (3) | C14—C15—C16—C22 | 175.91 (17) |
C2—C1—C6—C5 | −2.1 (3) | C22—C16—C17—C18 | −0.7 (3) |
C2—C1—C6—N2 | 177.96 (18) | C15—C16—C17—C18 | 179.21 (15) |
C4—C5—C6—C1 | 2.2 (3) | C16—C17—C18—C19 | 0.5 (3) |
C4—C5—C6—N2 | −177.92 (17) | C17—C18—C19—C21 | −0.2 (3) |
N2—C7—C8—C13 | 23.6 (2) | C17—C18—C19—C20 | 179.66 (17) |
C14—C7—C8—C13 | −91.3 (2) | C18—C19—C21—C22 | 0.0 (3) |
N2—C7—C8—C9 | −159.53 (15) | C20—C19—C21—C22 | −179.81 (19) |
C14—C7—C8—C9 | 85.6 (2) | C19—C21—C22—C16 | −0.2 (3) |
C13—C8—C9—C10 | 0.1 (3) | C17—C16—C22—C21 | 0.5 (3) |
C7—C8—C9—C10 | −176.90 (16) | C15—C16—C22—C21 | −179.36 (17) |
C8—C9—C10—C11 | 0.1 (3) | C16—C15—N1—N2 | 176.66 (14) |
C9—C10—C11—C12 | −0.1 (3) | C14—C15—N1—N2 | −2.50 (19) |
C9—C10—C11—F1 | −179.81 (15) | C15—N1—N2—C6 | 161.69 (15) |
C10—C11—C12—C13 | −0.2 (3) | C15—N1—N2—C7 | 0.88 (19) |
F1—C11—C12—C13 | 179.52 (16) | C1—C6—N2—N1 | −171.52 (16) |
C9—C8—C13—C12 | −0.4 (3) | C5—C6—N2—N1 | 8.6 (3) |
C7—C8—C13—C12 | 176.52 (16) | C1—C6—N2—C7 | −13.1 (3) |
C11—C12—C13—C8 | 0.5 (3) | C5—C6—N2—C7 | 167.00 (16) |
N2—C7—C14—C15 | −2.16 (18) | C8—C7—N2—N1 | −120.91 (15) |
C8—C7—C14—C15 | 119.24 (16) | C14—C7—N2—N1 | 0.97 (19) |
C7—C14—C15—N1 | 3.0 (2) | C8—C7—N2—C6 | 79.3 (2) |
C7—C14—C15—C16 | −176.13 (14) | C14—C7—N2—C6 | −158.79 (16) |
Experimental details
Crystal data | |
Chemical formula | C22H19FN2 |
Mr | 330.39 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 14.854 (3), 11.429 (2), 10.833 (2) |
β (°) | 109.090 (3) |
V (Å3) | 1738.0 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.45 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7135, 3066, 2155 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.133, 1.02 |
No. of reflections | 3066 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.19 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
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Pyrazolines are important and useful five-membered heterocyclic compounds. 1-Acetyl-3,5-diaryl-2-pyrazolines have been found to inhibit the monoamine oxidases (Manna et al., 2002). 1,3,5-Triaryl-2-pyrazolines were also used as scintillation solutes (Wiley et al., 1958). Here, we report the crystal structure of the title compound (I).
In the structure of (I) (Fig. 1), the values of the bond lengths and bond angles arel in the normal range (Guo et al., 2006). The mean plane of pyrazolinyl ring forms a dihedral angle of 18.52 (10)° with the phenyl ring, 71.69 (10)° with the fluorophenyl ring and 4.82 (10)° with the p-tolyl ring.