Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027833/lh2419sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027833/lh2419Isup2.hkl |
CCDC reference: 654930
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.109
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... 2 PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... 1
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The medicinal and biological properties of pyrazoline derivatives has been reported previously (Rawal et al., 1963; Dhal et al., 1975; Lombardino & Ottemes, 1981; Manna et al., 2002). The bond lengths and angles of the title compound are similar to related structures (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007).
1-(p-Nitrophenyl)-3-(p-fluorophenyl)-2-propenyl-1-ketone (0.02 mol)and hydrazine (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 a colourless solid. This solid was filtered and washed with water until the pH of the solution was ca 7.0. Finally, the solid was dry at 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, C—H distances 0.93–0.96 Å,respectively, and with Uiso = 1.2–1.5Ueq of the parent atoms.
Pyrazoline and its derivatives are useful compounds found to possess antiviral (Rawal et al., 1963), antifungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. 1-Acetyl-3,5-diaryl-2-pyrazoline has been found to inhibit the monoamine oxidases (Manna et al., 2002). As part of our ongoing investgation of pyrazolines and their metal complexes, we report here the crystal strucutre of the title compound.
In the molecule (Fig. 1), all of the bond lengthes and bond angles fall in the normal ranges (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007). The dihedral angles formed by pyrazolinyl ring with phenyl groups at positions 3 and 5 of the pyrazoline are 3.82 (8) and 66.57 (8)°, respectively. Intermolecular C—H···O hydrogen bonds help stabilize the crystal structure of.
The medicinal and biological properties of pyrazoline derivatives has been reported previously (Rawal et al., 1963; Dhal et al., 1975; Lombardino & Ottemes, 1981; Manna et al., 2002). The bond lengths and angles of the title compound are similar to related structures (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007).
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/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXTL/PC.
Fig. 1. The molecular structure and atom-labeling scheme with displacement ellipsoids drawn at the 30% probability level. |
C17H14FN3O3 | F(000) = 680 |
Mr = 327.31 | Dx = 1.420 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3251 reflections |
a = 5.7992 (11) Å | θ = 2.5–26.6° |
b = 16.661 (3) Å | µ = 0.11 mm−1 |
c = 16.056 (3) Å | T = 298 K |
β = 99.387 (2)° | Bar, colourless |
V = 1530.5 (5) Å3 | 0.50 × 0.25 × 0.21 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2326 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 25.5°, θmin = 1.8° |
φ and ω scans | h = −6→7 |
7736 measured reflections | k = −17→20 |
2826 independent reflections | l = −19→17 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.055P)2 + 0.2585P] where P = (Fo2 + 2Fc2)/3 |
2826 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C17H14FN3O3 | V = 1530.5 (5) Å3 |
Mr = 327.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.7992 (11) Å | µ = 0.11 mm−1 |
b = 16.661 (3) Å | T = 298 K |
c = 16.056 (3) Å | 0.50 × 0.25 × 0.21 mm |
β = 99.387 (2)° |
Bruker SMART CCD area-detector diffractometer | 2326 reflections with I > 2σ(I) |
7736 measured reflections | Rint = 0.023 |
2826 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.18 e Å−3 |
2826 reflections | Δρmin = −0.20 e Å−3 |
218 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 | 0.1716 (3) | 0.28095 (9) | 0.31214 (10) | 0.0497 (4) | |
H1 | 0.0514 | 0.2449 | 0.2940 | 0.060* | |
C2 | 0.1713 (3) | 0.32338 (10) | 0.38636 (10) | 0.0576 (4) | |
H2 | 0.0515 | 0.3163 | 0.4178 | 0.069* | |
C3 | 0.3486 (3) | 0.37541 (10) | 0.41247 (10) | 0.0591 (4) | |
C4 | 0.5251 (4) | 0.38828 (12) | 0.36756 (12) | 0.0691 (5) | |
H4 | 0.6436 | 0.4248 | 0.3862 | 0.083* | |
C5 | 0.5239 (3) | 0.34580 (11) | 0.29357 (11) | 0.0584 (4) | |
H5 | 0.6436 | 0.3538 | 0.2623 | 0.070* | |
C6 | 0.3472 (2) | 0.29139 (8) | 0.26500 (9) | 0.0422 (3) | |
C7 | 0.3543 (3) | 0.24768 (9) | 0.18283 (9) | 0.0459 (4) | |
H7 | 0.4945 | 0.2140 | 0.1882 | 0.055* | |
C8 | 0.3488 (3) | 0.30551 (11) | 0.10788 (9) | 0.0525 (4) | |
H8A | 0.3740 | 0.3606 | 0.1269 | 0.063* | |
H8B | 0.4653 | 0.2911 | 0.0735 | 0.063* | |
C9 | 0.1069 (3) | 0.29371 (9) | 0.06089 (8) | 0.0419 (3) | |
C10 | −0.0012 (3) | 0.34281 (8) | −0.01095 (8) | 0.0392 (3) | |
C11 | −0.2240 (3) | 0.32545 (9) | −0.05429 (9) | 0.0447 (4) | |
H11 | −0.3050 | 0.2816 | −0.0378 | 0.054* | |
C12 | −0.3259 (3) | 0.37190 (10) | −0.12099 (9) | 0.0486 (4) | |
H12 | −0.4751 | 0.3595 | −0.1489 | 0.058* | |
C13 | −0.2074 (3) | 0.43700 (9) | −0.14678 (9) | 0.0465 (4) | |
H13 | −0.2756 | 0.4693 | −0.1913 | 0.056* | |
C14 | 0.0134 (3) | 0.45268 (8) | −0.10489 (8) | 0.0401 (3) | |
C15 | 0.1209 (3) | 0.40736 (8) | −0.03730 (8) | 0.0398 (3) | |
H15 | 0.2709 | 0.4197 | −0.0102 | 0.048* | |
C16 | 0.1205 (3) | 0.12039 (10) | 0.17533 (10) | 0.0548 (4) | |
C17 | −0.0864 (4) | 0.07640 (11) | 0.13026 (12) | 0.0713 (6) | |
H17A | −0.0725 | 0.0708 | 0.0718 | 0.107* | |
H17B | −0.2260 | 0.1058 | 0.1350 | 0.107* | |
H17C | −0.0942 | 0.0242 | 0.1550 | 0.107* | |
F1 | 0.3487 (2) | 0.41655 (7) | 0.48573 (7) | 0.0914 (4) | |
N1 | 0.1449 (2) | 0.19873 (8) | 0.15372 (7) | 0.0490 (3) | |
N2 | −0.0014 (2) | 0.23332 (7) | 0.08576 (7) | 0.0466 (3) | |
N3 | 0.1435 (2) | 0.52153 (7) | −0.13096 (8) | 0.0483 (3) | |
O1 | 0.2651 (3) | 0.09008 (7) | 0.22967 (8) | 0.0733 (4) | |
O2 | 0.3452 (2) | 0.53098 (7) | −0.09699 (8) | 0.0662 (4) | |
O3 | 0.0411 (2) | 0.56620 (7) | −0.18506 (8) | 0.0696 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0534 (10) | 0.0437 (8) | 0.0520 (9) | −0.0073 (7) | 0.0088 (7) | 0.0059 (7) |
C2 | 0.0713 (12) | 0.0525 (10) | 0.0529 (9) | 0.0023 (8) | 0.0215 (8) | 0.0073 (7) |
C3 | 0.0758 (12) | 0.0501 (10) | 0.0496 (9) | 0.0042 (9) | 0.0046 (8) | −0.0025 (7) |
C4 | 0.0653 (12) | 0.0657 (12) | 0.0723 (12) | −0.0146 (9) | −0.0012 (10) | −0.0138 (9) |
C5 | 0.0499 (10) | 0.0642 (11) | 0.0617 (10) | −0.0105 (8) | 0.0105 (8) | −0.0009 (8) |
C6 | 0.0426 (8) | 0.0395 (8) | 0.0431 (8) | 0.0004 (6) | 0.0028 (6) | 0.0096 (6) |
C7 | 0.0446 (8) | 0.0470 (8) | 0.0459 (8) | −0.0014 (7) | 0.0065 (7) | 0.0067 (7) |
C8 | 0.0512 (10) | 0.0637 (10) | 0.0430 (8) | −0.0079 (8) | 0.0093 (7) | 0.0111 (7) |
C9 | 0.0494 (9) | 0.0407 (8) | 0.0371 (7) | −0.0017 (6) | 0.0118 (6) | −0.0015 (6) |
C10 | 0.0463 (8) | 0.0379 (7) | 0.0352 (7) | 0.0011 (6) | 0.0120 (6) | −0.0032 (6) |
C11 | 0.0482 (9) | 0.0427 (8) | 0.0451 (8) | −0.0039 (6) | 0.0129 (6) | −0.0024 (6) |
C12 | 0.0442 (9) | 0.0531 (9) | 0.0474 (8) | −0.0013 (7) | 0.0039 (7) | −0.0049 (7) |
C13 | 0.0532 (9) | 0.0457 (8) | 0.0405 (8) | 0.0081 (7) | 0.0067 (7) | 0.0014 (6) |
C14 | 0.0500 (9) | 0.0334 (7) | 0.0387 (7) | 0.0018 (6) | 0.0126 (6) | −0.0026 (6) |
C15 | 0.0436 (8) | 0.0389 (7) | 0.0376 (7) | −0.0006 (6) | 0.0084 (6) | −0.0038 (6) |
C16 | 0.0752 (12) | 0.0448 (9) | 0.0433 (8) | −0.0074 (8) | 0.0062 (8) | 0.0038 (7) |
C17 | 0.0936 (15) | 0.0519 (10) | 0.0634 (11) | −0.0215 (10) | −0.0018 (10) | 0.0059 (8) |
F1 | 0.1220 (11) | 0.0845 (8) | 0.0669 (7) | 0.0009 (7) | 0.0134 (7) | −0.0266 (6) |
N1 | 0.0603 (8) | 0.0426 (7) | 0.0417 (6) | −0.0075 (6) | 0.0011 (6) | 0.0059 (5) |
N2 | 0.0562 (8) | 0.0426 (7) | 0.0399 (6) | −0.0049 (6) | 0.0045 (6) | 0.0026 (5) |
N3 | 0.0611 (9) | 0.0362 (7) | 0.0501 (7) | 0.0019 (6) | 0.0164 (6) | 0.0012 (6) |
O1 | 0.0935 (10) | 0.0537 (7) | 0.0648 (8) | −0.0072 (6) | −0.0107 (7) | 0.0180 (6) |
O2 | 0.0631 (8) | 0.0568 (7) | 0.0771 (8) | −0.0177 (6) | 0.0060 (7) | 0.0093 (6) |
O3 | 0.0817 (9) | 0.0512 (7) | 0.0761 (8) | 0.0083 (6) | 0.0138 (7) | 0.0260 (6) |
C1—C6 | 1.375 (2) | C10—C15 | 1.391 (2) |
C1—C2 | 1.386 (2) | C10—C11 | 1.394 (2) |
C1—H1 | 0.9300 | C11—C12 | 1.374 (2) |
C2—C3 | 1.358 (3) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—C13 | 1.383 (2) |
C3—F1 | 1.3613 (19) | C12—H12 | 0.9300 |
C3—C4 | 1.362 (3) | C13—C14 | 1.371 (2) |
C4—C5 | 1.382 (2) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | C14—C15 | 1.3842 (19) |
C5—C6 | 1.389 (2) | C14—N3 | 1.4709 (19) |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C6—C7 | 1.513 (2) | C16—O1 | 1.217 (2) |
C7—N1 | 1.4745 (19) | C16—N1 | 1.364 (2) |
C7—C8 | 1.538 (2) | C16—C17 | 1.489 (2) |
C7—H7 | 0.9800 | C17—H17A | 0.9600 |
C8—C9 | 1.494 (2) | C17—H17B | 0.9600 |
C8—H8A | 0.9700 | C17—H17C | 0.9600 |
C8—H8B | 0.9700 | N1—N2 | 1.3930 (17) |
C9—N2 | 1.2841 (18) | N3—O2 | 1.2176 (17) |
C9—C10 | 1.4686 (19) | N3—O3 | 1.2219 (17) |
C6—C1—C2 | 120.90 (15) | C15—C10—C9 | 119.73 (13) |
C6—C1—H1 | 119.5 | C11—C10—C9 | 121.26 (13) |
C2—C1—H1 | 119.5 | C12—C11—C10 | 121.21 (14) |
C3—C2—C1 | 118.94 (16) | C12—C11—H11 | 119.4 |
C3—C2—H2 | 120.5 | C10—C11—H11 | 119.4 |
C1—C2—H2 | 120.5 | C11—C12—C13 | 120.20 (14) |
C2—C3—F1 | 118.79 (17) | C11—C12—H12 | 119.9 |
C2—C3—C4 | 122.27 (16) | C13—C12—H12 | 119.9 |
F1—C3—C4 | 118.94 (17) | C14—C13—C12 | 118.20 (14) |
C3—C4—C5 | 118.41 (17) | C14—C13—H13 | 120.9 |
C3—C4—H4 | 120.8 | C12—C13—H13 | 120.9 |
C5—C4—H4 | 120.8 | C13—C14—C15 | 123.10 (14) |
C4—C5—C6 | 121.22 (16) | C13—C14—N3 | 119.37 (13) |
C4—C5—H5 | 119.4 | C15—C14—N3 | 117.51 (13) |
C6—C5—H5 | 119.4 | C14—C15—C10 | 118.25 (14) |
C1—C6—C5 | 118.26 (14) | C14—C15—H15 | 120.9 |
C1—C6—C7 | 123.15 (14) | C10—C15—H15 | 120.9 |
C5—C6—C7 | 118.58 (13) | O1—C16—N1 | 119.46 (15) |
N1—C7—C6 | 113.84 (12) | O1—C16—C17 | 123.41 (15) |
N1—C7—C8 | 100.81 (11) | N1—C16—C17 | 117.13 (15) |
C6—C7—C8 | 112.37 (13) | C16—C17—H17A | 109.5 |
N1—C7—H7 | 109.8 | C16—C17—H17B | 109.5 |
C6—C7—H7 | 109.8 | H17A—C17—H17B | 109.5 |
C8—C7—H7 | 109.8 | C16—C17—H17C | 109.5 |
C9—C8—C7 | 102.17 (12) | H17A—C17—H17C | 109.5 |
C9—C8—H8A | 111.3 | H17B—C17—H17C | 109.5 |
C7—C8—H8A | 111.3 | C16—N1—N2 | 121.34 (13) |
C9—C8—H8B | 111.3 | C16—N1—C7 | 124.25 (13) |
C7—C8—H8B | 111.3 | N2—N1—C7 | 112.62 (11) |
H8A—C8—H8B | 109.2 | C9—N2—N1 | 107.54 (12) |
N2—C9—C10 | 120.84 (13) | O2—N3—O3 | 124.03 (14) |
N2—C9—C8 | 114.40 (13) | O2—N3—C14 | 118.26 (13) |
C10—C9—C8 | 124.69 (13) | O3—N3—C14 | 117.70 (14) |
C15—C10—C11 | 119.01 (13) | ||
C6—C1—C2—C3 | −0.4 (2) | C10—C11—C12—C13 | 0.4 (2) |
C1—C2—C3—F1 | −179.51 (14) | C11—C12—C13—C14 | 0.9 (2) |
C1—C2—C3—C4 | 1.0 (3) | C12—C13—C14—C15 | −1.2 (2) |
C2—C3—C4—C5 | −0.9 (3) | C12—C13—C14—N3 | 180.00 (12) |
F1—C3—C4—C5 | 179.60 (16) | C13—C14—C15—C10 | 0.1 (2) |
C3—C4—C5—C6 | 0.3 (3) | N3—C14—C15—C10 | 178.97 (12) |
C2—C1—C6—C5 | −0.2 (2) | C11—C10—C15—C14 | 1.16 (19) |
C2—C1—C6—C7 | −179.00 (14) | C9—C10—C15—C14 | −179.63 (12) |
C4—C5—C6—C1 | 0.3 (2) | O1—C16—N1—N2 | 172.89 (15) |
C4—C5—C6—C7 | 179.14 (16) | C17—C16—N1—N2 | −7.4 (2) |
C1—C6—C7—N1 | 5.5 (2) | O1—C16—N1—C7 | 9.3 (2) |
C5—C6—C7—N1 | −173.28 (14) | C17—C16—N1—C7 | −170.99 (15) |
C1—C6—C7—C8 | 119.32 (15) | C6—C7—N1—C16 | −89.44 (18) |
C5—C6—C7—C8 | −59.47 (18) | C8—C7—N1—C16 | 150.03 (15) |
N1—C7—C8—C9 | 14.43 (15) | C6—C7—N1—N2 | 105.70 (14) |
C6—C7—C8—C9 | −107.14 (14) | C8—C7—N1—N2 | −14.83 (16) |
C7—C8—C9—N2 | −11.41 (17) | C10—C9—N2—N1 | 179.48 (12) |
C7—C8—C9—C10 | 171.64 (13) | C8—C9—N2—N1 | 2.40 (17) |
N2—C9—C10—C15 | −179.24 (13) | C16—N1—N2—C9 | −156.81 (14) |
C8—C9—C10—C15 | −2.5 (2) | C7—N1—N2—C9 | 8.55 (17) |
N2—C9—C10—C11 | −0.1 (2) | C13—C14—N3—O2 | −174.83 (13) |
C8—C9—C10—C11 | 176.70 (14) | C15—C14—N3—O2 | 6.29 (19) |
C15—C10—C11—C12 | −1.4 (2) | C13—C14—N3—O3 | 5.8 (2) |
C9—C10—C11—C12 | 179.36 (12) | C15—C14—N3—O3 | −173.06 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···02i | 0.97 | 2.53 | 3.271 (2) | 133 |
C12—H12···01ii | 0.93 | 2.41 | 3.150 (2) | 136 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, −y−1/2, z−3/2. |
Experimental details
Crystal data | |
Chemical formula | C17H14FN3O3 |
Mr | 327.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 5.7992 (11), 16.661 (3), 16.056 (3) |
β (°) | 99.387 (2) |
V (Å3) | 1530.5 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.50 × 0.25 × 0.21 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7736, 2826, 2326 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.109, 1.05 |
No. of reflections | 2826 |
No. of parameters | 218 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.20 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), SHELXTL/PC.
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···02i | 0.97 | 2.53 | 3.271 (2) | 133 |
C12—H12···01ii | 0.93 | 2.41 | 3.150 (2) | 136 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, −y−1/2, z−3/2. |
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Pyrazoline and its derivatives are useful compounds found to possess antiviral (Rawal et al., 1963), antifungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. 1-Acetyl-3,5-diaryl-2-pyrazoline has been found to inhibit the monoamine oxidases (Manna et al., 2002). As part of our ongoing investgation of pyrazolines and their metal complexes, we report here the crystal strucutre of the title compound.
In the molecule (Fig. 1), all of the bond lengthes and bond angles fall in the normal ranges (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007). The dihedral angles formed by pyrazolinyl ring with phenyl groups at positions 3 and 5 of the pyrazoline are 3.82 (8) and 66.57 (8)°, respectively. Intermolecular C—H···O hydrogen bonds help stabilize the crystal structure of.