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Acta Cryst. (2007). E63, o2980    [ doi:10.1107/S1600536807024634 ]

3-(4-Fluorophenyl)-1-phenyl-5-(p-tolyl)-2-pyrazoline

H.-M. Guo, F.-F. Jian, J. Wang, B.-Y. Huang and Y. Zhang

Abstract top

The title compound, C22H19FN2, was prepared by reacting phenylhydrazine with 1-(4-fluorophenyl)-3-(p-tolyl)prop-2-enone. The pyrazoline ring forms a dihedral angle of 5.2 (3)° with the phenyl ring, 8.8 (1)° with the fluorophenyl ring and 80.7 (2)° with the p-tolyl ring.

Comment top

As important and useful five-membered heterocyclic compounds, pyrazoline and its derivatives were found to possess antiviral (Rawal et al., 1963), antifungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) properties. Several 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, a functionalized pyrazoline (Fig. 1). All bond lengths and angles fall in the normal ranges (Rurack et al., 2000; Fahrni et al., 2003; Guo et al., 2006; Foces-Foces et al., 2001). The mean plane of the pyrazoline ring, N1/N2/C7/C8/C9 makes dihedral angles of 80.7 (2), 8.8 (1) and 5.2 (3)° with the benzene ring C10/C11/C12/C13/C14/C15, the benzene ring C1/C2/C3/C4/C5/C6, and the phenyl ring C17/C18/C19/C20/C21/C22, respectively.

Related literature top

For literature about properties of pyrazoline derivatives, see: Dhal et al. (1975); Fahrni et al. (2003); Lombardino & Ottemes (1981); Rawal et al. (1963); Rurack et al. (2000); Wiley et al. (1958). Two X-ray structures closely related to that of the title compound were previously reported (Foces-Foces et al., 2001; Guo et al., 2006).

Experimental top

Amounts of 1-(4-fluorophenyl)-3-(p-tolyl)-2-propenone (0.02 mol) and phenylhydrazine (0.02 mol) were mixed in 99.5% acetic acid (40 ml) and refluxed 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 was ca. 7. Yellow single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from EtOH at room temperature.

Refinement top

H atoms were placed geometrically and allowed to ride on their parent atoms, with C—H distances constrained to 0.93 (aromatic CH), 0.97 (methylene CH2) aor 0.98 Å (methine CH), and with Uiso(H) = 1.2Ueq(carrier C).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure and atom-labeling scheme for the title molecule, with displacement ellipsoids drawn at the 30% probability level.
3-(4-Fluorophenyl)-1-phenyl-5-(p-tolyl)-2-pyrazoline top
Crystal data top
C22H19FN2F(000) = 696
Mr = 330.39Dx = 1.256 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1300 reflections
a = 20.050 (2) Åθ = 2.5–22.9°
b = 5.588 (3) ŵ = 0.08 mm−1
c = 16.480 (2) ÅT = 294 K
β = 108.913 (19)°Block, yellow
V = 1747 (4) Å30.30 × 0.24 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		3081 independent reflections
Radiation source: fine-focus sealed tube1371 reflections with I > 2σ(I)
graphiteRint = 0.089
φ and ω scansθmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −23→23
Tmin = 0.976, Tmax = 0.984k = −6→5
8200 measured reflectionsl = −16→19
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.222 w = 1/[σ2(Fo2)]
where P = (Fo2 + 2Fc2)/3
S = 0.91(Δ/σ)max < 0.001
3081 reflectionsΔρmax = 0.17 e Å−3
228 parametersΔρmin = −0.19 e Å−3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (3)
Crystal data top
C22H19FN2V = 1747 (4) Å3
Mr = 330.39Z = 4
Monoclinic, P21/cMo Kα radiation
a = 20.050 (2) ŵ = 0.08 mm−1
b = 5.588 (3) ÅT = 294 K
c = 16.480 (2) Å0.30 × 0.24 × 0.20 mm
β = 108.913 (19)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3081 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		1371 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.984Rint = 0.089
8200 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.222Δρmax = 0.17 e Å−3
S = 0.91Δρmin = −0.19 e Å−3
3081 reflectionsAbsolute structure: ?
228 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.47935 (9)0.2677 (5)0.44618 (15)0.0950 (9)
N10.67472 (13)0.4524 (6)0.21806 (17)0.0555 (9)
N20.72962 (13)0.4153 (6)0.18606 (18)0.0629 (9)
C10.57510 (17)0.4651 (7)0.3086 (2)0.0578 (10)
H10.57440.59090.27140.069*
C20.52539 (17)0.4577 (7)0.3500 (2)0.0616 (11)
H20.49090.57540.34050.074*
C30.52810 (16)0.2733 (8)0.4051 (2)0.0640 (12)
C40.57658 (18)0.0955 (8)0.4198 (2)0.0663 (11)
H40.5765−0.02930.45710.080*
C50.62618 (17)0.1041 (7)0.3778 (2)0.0576 (10)
H50.6601−0.01560.38750.069*
C60.62597 (15)0.2896 (7)0.3213 (2)0.0505 (9)
C70.67859 (15)0.2964 (7)0.2776 (2)0.0505 (9)
C80.73981 (17)0.1281 (7)0.2917 (2)0.0621 (11)
H8A0.7238−0.03210.27210.074*
H8B0.76820.12170.35180.074*
C90.78135 (16)0.2389 (7)0.2373 (2)0.0564 (10)
H90.79000.11680.19920.068*
C100.85006 (16)0.3557 (7)0.2878 (2)0.0541 (10)
C110.91418 (18)0.2616 (7)0.2897 (2)0.0645 (11)
H110.91540.12030.26040.077*
C120.97669 (19)0.3746 (9)0.3345 (3)0.0728 (13)
H121.01920.30650.33510.087*
C130.97758 (19)0.5875 (8)0.3786 (2)0.0674 (12)
C140.91340 (19)0.6792 (8)0.3770 (2)0.0700 (11)
H140.91220.82050.40630.084*
C150.85109 (19)0.5671 (8)0.3333 (2)0.0629 (11)
H150.80870.63360.33390.075*
C161.04571 (19)0.7126 (9)0.4272 (3)0.0934 (15)
H16A1.04640.86900.40330.140*
H16B1.08490.62100.42270.140*
H16C1.04920.72730.48650.140*
C170.73954 (16)0.5733 (7)0.1260 (2)0.0510 (10)
C180.79532 (18)0.5398 (8)0.0943 (2)0.0677 (12)
H180.82570.41060.11290.081*
C190.80556 (19)0.6973 (9)0.0355 (2)0.0763 (13)
H190.84390.67550.01620.092*
C200.76105 (19)0.8849 (9)0.0048 (2)0.0723 (12)
H200.76830.9895−0.03540.087*
C210.70498 (17)0.9152 (8)0.0348 (2)0.0686 (12)
H210.67391.04150.01400.082*
C220.69399 (16)0.7640 (7)0.0945 (2)0.0572 (11)
H220.65590.78880.11400.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0643 (13)0.129 (2)0.1097 (19)−0.0038 (14)0.0529 (13)0.0221 (16)
N10.0469 (15)0.075 (2)0.0486 (17)0.0069 (16)0.0208 (14)0.0043 (17)
N20.0556 (16)0.082 (2)0.0600 (18)0.0223 (17)0.0312 (15)0.0262 (18)
C10.0478 (19)0.073 (3)0.051 (2)0.000 (2)0.0143 (18)0.008 (2)
C20.0445 (19)0.080 (3)0.060 (2)0.004 (2)0.0172 (18)0.002 (2)
C30.0378 (18)0.100 (4)0.058 (2)−0.014 (2)0.0207 (18)0.004 (2)
C40.053 (2)0.084 (3)0.065 (2)−0.013 (2)0.023 (2)0.014 (2)
C50.0502 (19)0.066 (3)0.058 (2)−0.006 (2)0.0187 (18)0.005 (2)
C60.0395 (17)0.068 (3)0.0424 (18)−0.0103 (19)0.0103 (15)−0.003 (2)
C70.0457 (18)0.066 (3)0.0413 (18)0.0001 (19)0.0157 (16)0.002 (2)
C80.059 (2)0.068 (3)0.063 (2)0.004 (2)0.0263 (18)0.005 (2)
C90.056 (2)0.065 (3)0.055 (2)0.012 (2)0.0271 (18)0.011 (2)
C100.053 (2)0.065 (3)0.052 (2)0.010 (2)0.0276 (18)0.011 (2)
C110.061 (2)0.069 (3)0.073 (3)0.010 (2)0.035 (2)0.003 (2)
C120.057 (2)0.087 (4)0.083 (3)0.012 (2)0.035 (2)0.020 (3)
C130.066 (2)0.081 (3)0.062 (2)−0.004 (3)0.031 (2)0.015 (2)
C140.074 (3)0.073 (3)0.071 (3)−0.004 (2)0.035 (2)−0.002 (2)
C150.061 (2)0.069 (3)0.067 (2)0.011 (2)0.031 (2)0.004 (2)
C160.077 (3)0.111 (4)0.093 (3)−0.022 (3)0.028 (2)0.014 (3)
C170.0434 (18)0.071 (3)0.0363 (18)0.0020 (19)0.0091 (16)0.0070 (19)
C180.064 (2)0.090 (3)0.057 (2)0.014 (2)0.030 (2)0.017 (2)
C190.058 (2)0.119 (4)0.057 (2)0.007 (3)0.026 (2)0.015 (3)
C200.062 (2)0.103 (4)0.053 (2)−0.006 (3)0.019 (2)0.022 (2)
C210.056 (2)0.084 (3)0.059 (2)0.002 (2)0.0089 (19)0.020 (2)
C220.0396 (18)0.080 (3)0.048 (2)0.001 (2)0.0085 (16)0.009 (2)
Geometric parameters (Å, °) top
F1—C31.358 (4)C11—C121.384 (5)
N1—C71.296 (4)C11—H110.9300
N1—N21.382 (3)C12—C131.392 (6)
N2—C171.388 (4)C12—H120.9300
N2—C91.481 (4)C13—C141.377 (5)
C1—C21.378 (4)C13—C161.512 (5)
C1—C61.381 (5)C14—C151.375 (5)
C1—H10.9300C14—H140.9300
C2—C31.363 (5)C15—H150.9300
C2—H20.9300C16—H16A0.9600
C3—C41.356 (5)C16—H16B0.9600
C4—C51.384 (4)C16—H16C0.9600
C4—H40.9300C17—C221.390 (5)
C5—C61.392 (5)C17—C181.392 (4)
C5—H50.9300C18—C191.373 (5)
C6—C71.459 (4)C18—H180.9300
C7—C81.503 (5)C19—C201.363 (6)
C8—C91.538 (4)C19—H190.9300
C8—H8A0.9700C20—C211.377 (5)
C8—H8B0.9700C20—H200.9300
C9—C101.508 (5)C21—C221.368 (5)
C9—H90.9800C21—H210.9300
C10—C111.380 (5)C22—H220.9300
C10—C151.395 (5)
C7—N1—N2109.2 (3)C10—C11—C12120.9 (4)
N1—N2—C17119.5 (3)C10—C11—H11119.5
N1—N2—C9112.3 (3)C12—C11—H11119.5
C17—N2—C9126.5 (3)C11—C12—C13121.7 (4)
C2—C1—C6121.4 (3)C11—C12—H12119.2
C2—C1—H1119.3C13—C12—H12119.2
C6—C1—H1119.3C14—C13—C12117.0 (4)
C3—C2—C1118.3 (3)C14—C13—C16121.1 (4)
C3—C2—H2120.9C12—C13—C16121.9 (4)
C1—C2—H2120.9C15—C14—C13121.7 (4)
C4—C3—F1119.0 (4)C15—C14—H14119.2
C4—C3—C2122.9 (3)C13—C14—H14119.2
F1—C3—C2118.1 (4)C14—C15—C10121.4 (3)
C3—C4—C5118.4 (4)C14—C15—H15119.3
C3—C4—H4120.8C10—C15—H15119.3
C5—C4—H4120.8C13—C16—H16A109.5
C4—C5—C6120.9 (4)C13—C16—H16B109.5
C4—C5—H5119.6H16A—C16—H16B109.5
C6—C5—H5119.6C13—C16—H16C109.5
C1—C6—C5118.2 (3)H16A—C16—H16C109.5
C1—C6—C7121.6 (3)H16B—C16—H16C109.5
C5—C6—C7120.3 (3)N2—C17—C22121.7 (3)
N1—C7—C6121.1 (3)N2—C17—C18120.0 (3)
N1—C7—C8112.6 (3)C22—C17—C18118.2 (3)
C6—C7—C8126.3 (3)C19—C18—C17120.1 (4)
C7—C8—C9103.1 (3)C19—C18—H18120.0
C7—C8—H8A111.1C17—C18—H18120.0
C9—C8—H8A111.1C20—C19—C18121.7 (3)
C7—C8—H8B111.1C20—C19—H19119.1
C9—C8—H8B111.1C18—C19—H19119.1
H8A—C8—H8B109.1C19—C20—C21118.3 (3)
N2—C9—C10111.9 (3)C19—C20—H20120.9
N2—C9—C8100.9 (2)C21—C20—H20120.9
C10—C9—C8115.0 (3)C22—C21—C20121.5 (4)
N2—C9—H9109.6C22—C21—H21119.2
C10—C9—H9109.6C20—C21—H21119.2
C8—C9—H9109.6C21—C22—C17120.2 (3)
C11—C10—C15117.3 (3)C21—C22—H22119.9
C11—C10—C9121.7 (3)C17—C22—H22119.9
C15—C10—C9121.0 (3)
C7—N1—N2—C17−175.0 (3)N2—C9—C10—C11−133.7 (3)
C7—N1—N2—C9−8.9 (4)C8—C9—C10—C11112.0 (4)
C6—C1—C2—C30.9 (5)N2—C9—C10—C1544.9 (4)
C1—C2—C3—C4−1.2 (6)C8—C9—C10—C15−69.4 (4)
C1—C2—C3—F1179.5 (3)C15—C10—C11—C12−0.4 (5)
F1—C3—C4—C5−179.7 (3)C9—C10—C11—C12178.3 (3)
C2—C3—C4—C51.1 (6)C10—C11—C12—C13−0.6 (6)
C3—C4—C5—C6−0.6 (5)C11—C12—C13—C141.1 (6)
C2—C1—C6—C5−0.4 (5)C11—C12—C13—C16−179.6 (3)
C2—C1—C6—C7179.9 (3)C12—C13—C14—C15−0.6 (6)
C4—C5—C6—C10.3 (5)C16—C13—C14—C15−179.9 (3)
C4—C5—C6—C7180.0 (3)C13—C14—C15—C10−0.5 (6)
N2—N1—C7—C6−178.4 (3)C11—C10—C15—C141.0 (5)
N2—N1—C7—C8−0.5 (4)C9—C10—C15—C14−177.7 (3)
C1—C6—C7—N1−7.8 (5)N1—N2—C17—C22−2.5 (5)
C5—C6—C7—N1172.5 (3)C9—N2—C17—C22−166.4 (3)
C1—C6—C7—C8174.6 (3)N1—N2—C17—C18179.0 (3)
C5—C6—C7—C8−5.1 (5)C9—N2—C17—C1815.1 (5)
N1—C7—C8—C98.9 (4)N2—C17—C18—C19−179.4 (4)
C6—C7—C8—C9−173.3 (3)C22—C17—C18—C192.1 (5)
N1—N2—C9—C10−109.1 (3)C17—C18—C19—C20−1.9 (6)
C17—N2—C9—C1055.8 (4)C18—C19—C20—C210.5 (6)
N1—N2—C9—C813.7 (4)C19—C20—C21—C220.6 (6)
C17—N2—C9—C8178.6 (3)C20—C21—C22—C17−0.4 (6)
C7—C8—C9—N2−12.6 (3)N2—C17—C22—C21−179.5 (3)
C7—C8—C9—C10108.0 (3)C18—C17—C22—C21−0.9 (5)
Acknowledgements top

The authors thank the Natural Science Foundation of Shandong Province (grant No. Y2005B04) and the Doctoral Fund of Qingdao University of Science and Technology.

references
References top

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