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In the title compound, C22H19FN2, the mean plane of the pyrazoline ring forms dihedral angles of 18.52 (10)° with the phenyl ring, 71.69 (10)° with the fluoro­phenyl ring and 4.82 (10)° with the p-tolyl ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028711/at2325sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028711/at2325Isup2.hkl
Contains datablock I

CCDC reference: 654965

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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.

Related literature top

For related literature, see: Guo et al. (2006); Manna et al. (2002); Wiley et al. (1958).

Experimental top

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.

Refinement top

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.

Structure description top

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).

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 (I), with displacement ellipsoids drawn at the 30% probability level.
5-(4-Fluorophenyl)-3-(4-methylphenyl)-1-phenyl-2-pyrazoline top
Crystal data top
C22H19FN2F(000) = 696
Mr = 330.39Dx = 1.263 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2776 reflections
a = 14.854 (3) Åθ = 2.3–24.0°
b = 11.429 (2) ŵ = 0.08 mm1
c = 10.833 (2) ÅT = 298 K
β = 109.090 (3)°Block, yellow
V = 1738.0 (6) Å30.50 × 0.45 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2155 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
φ and ω scansh = 1716
7135 measured reflectionsk = 1213
3066 independent reflectionsl = 1112
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-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 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C22H19FN2V = 1738.0 (6) Å3
Mr = 330.39Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.854 (3) ŵ = 0.08 mm1
b = 11.429 (2) ÅT = 298 K
c = 10.833 (2) Å0.50 × 0.45 × 0.10 mm
β = 109.090 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2155 reflections with I > 2σ(I)
7135 measured reflectionsRint = 0.020
3066 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.02Δρmax = 0.16 e Å3
3066 reflectionsΔρmin = 0.19 e Å3
227 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
xyzUiso*/Ueq
C10.84586 (13)1.01263 (17)0.0443 (2)0.0773 (5)
H10.84300.93880.08140.093*
C20.90293 (14)1.09809 (18)0.07041 (19)0.0812 (5)
H20.93791.08140.12550.097*
C30.90851 (13)1.20709 (18)0.0161 (2)0.0848 (6)
H30.94601.26500.03510.102*
C40.85805 (13)1.22952 (17)0.0669 (2)0.0845 (6)
H40.86251.30290.10550.101*
C50.80102 (12)1.14601 (16)0.09424 (19)0.0739 (5)
H50.76771.16280.15140.089*
C60.79317 (12)1.03656 (15)0.03659 (17)0.0650 (4)
C70.70449 (13)0.84353 (15)0.01505 (18)0.0730 (5)
H70.68900.86040.10840.088*
C80.78013 (12)0.75006 (14)0.02456 (16)0.0616 (4)
C90.77887 (13)0.65943 (16)0.06012 (17)0.0711 (5)
H90.73290.65930.14260.085*
C100.84354 (14)0.56954 (17)0.0260 (2)0.0791 (5)
H100.84200.50900.08400.095*
C110.90948 (13)0.57141 (17)0.0943 (2)0.0755 (5)
C120.91423 (13)0.65768 (19)0.18137 (19)0.0817 (6)
H120.96040.65630.26360.098*
C130.84913 (14)0.74803 (17)0.14589 (17)0.0756 (5)
H130.85190.80830.20470.091*
C140.61277 (13)0.81138 (17)0.0143 (2)0.0825 (6)
H14A0.55780.81230.06470.099*
H14B0.61800.73480.05450.099*
C150.60609 (11)0.90527 (14)0.10650 (16)0.0612 (4)
C160.53417 (11)0.91201 (14)0.17113 (16)0.0617 (4)
C170.46009 (12)0.83265 (16)0.14551 (19)0.0753 (5)
H170.45520.77360.08460.090*
C180.39311 (12)0.83949 (18)0.2089 (2)0.0812 (6)
H180.34440.78440.19000.097*
C190.39667 (12)0.92547 (16)0.29887 (19)0.0737 (5)
C200.32370 (13)0.9332 (2)0.3669 (2)0.0968 (7)
H20A0.26690.89300.31630.145*
H20B0.30911.01380.37640.145*
H20C0.34840.89760.45160.145*
C210.47016 (14)1.00439 (18)0.3234 (2)0.0862 (6)
H210.47461.06370.38380.103*
C220.53736 (13)0.99869 (17)0.2615 (2)0.0810 (6)
H220.58591.05410.28080.097*
F10.97450 (8)0.48320 (11)0.13006 (15)0.1102 (5)
N10.67233 (10)0.98251 (12)0.12690 (13)0.0657 (4)
N20.73301 (11)0.95237 (12)0.06048 (16)0.0777 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0876 (12)0.0718 (11)0.0851 (13)0.0018 (9)0.0454 (11)0.0045 (10)
C20.0812 (12)0.0913 (14)0.0851 (13)0.0026 (10)0.0462 (10)0.0124 (11)
C30.0767 (11)0.0812 (13)0.1082 (16)0.0091 (10)0.0461 (11)0.0126 (12)
C40.0788 (12)0.0689 (11)0.1175 (16)0.0094 (9)0.0480 (12)0.0024 (11)
C50.0719 (10)0.0672 (11)0.0941 (13)0.0009 (9)0.0430 (10)0.0006 (10)
C60.0659 (9)0.0604 (10)0.0760 (11)0.0025 (8)0.0331 (9)0.0074 (8)
C70.0870 (11)0.0666 (11)0.0736 (11)0.0032 (9)0.0376 (9)0.0034 (9)
C80.0734 (10)0.0604 (9)0.0608 (10)0.0114 (8)0.0354 (9)0.0045 (8)
C90.0782 (11)0.0760 (11)0.0635 (11)0.0098 (10)0.0293 (9)0.0112 (9)
C100.0902 (13)0.0680 (12)0.0921 (14)0.0091 (10)0.0476 (12)0.0156 (10)
C110.0734 (11)0.0673 (11)0.0992 (15)0.0039 (9)0.0467 (11)0.0090 (11)
C120.0800 (12)0.0912 (14)0.0733 (12)0.0115 (11)0.0242 (10)0.0079 (11)
C130.0938 (12)0.0746 (12)0.0628 (11)0.0103 (11)0.0315 (10)0.0103 (9)
C140.0778 (11)0.0760 (12)0.0999 (14)0.0071 (9)0.0377 (10)0.0111 (11)
C150.0616 (9)0.0561 (9)0.0644 (10)0.0025 (8)0.0187 (8)0.0083 (8)
C160.0553 (9)0.0582 (9)0.0702 (11)0.0039 (7)0.0187 (8)0.0115 (8)
C170.0630 (10)0.0696 (11)0.0913 (13)0.0031 (9)0.0225 (9)0.0051 (10)
C180.0544 (9)0.0796 (13)0.1092 (15)0.0072 (9)0.0261 (10)0.0081 (12)
C190.0603 (10)0.0727 (11)0.0917 (13)0.0054 (9)0.0297 (9)0.0128 (10)
C200.0713 (12)0.1072 (16)0.1243 (18)0.0014 (11)0.0491 (12)0.0124 (13)
C210.0844 (12)0.0781 (12)0.1126 (16)0.0115 (10)0.0550 (12)0.0112 (11)
C220.0751 (11)0.0708 (12)0.1084 (15)0.0156 (9)0.0454 (11)0.0075 (11)
F10.0939 (8)0.0929 (8)0.1555 (12)0.0150 (7)0.0567 (8)0.0225 (8)
N10.0708 (9)0.0589 (8)0.0762 (9)0.0022 (7)0.0361 (7)0.0072 (7)
N20.0917 (10)0.0588 (8)0.1033 (12)0.0085 (7)0.0600 (9)0.0090 (8)
Geometric parameters (Å, º) top
C1—C61.380 (2)C12—C131.381 (3)
C1—C21.382 (3)C12—H120.9300
C1—H10.9300C13—H130.9300
C2—C31.369 (3)C14—C151.492 (3)
C2—H20.9300C14—H14A0.9700
C3—C41.369 (3)C14—H14B0.9700
C3—H30.9300C15—N11.2862 (19)
C4—C51.371 (2)C15—C161.458 (2)
C4—H40.9300C16—C171.382 (2)
C5—C61.386 (2)C16—C221.383 (3)
C5—H50.9300C17—C181.383 (3)
C6—N21.394 (2)C17—H170.9300
C7—N21.473 (2)C18—C191.373 (3)
C7—C81.507 (2)C18—H180.9300
C7—C141.541 (2)C19—C211.373 (3)
C7—H70.9800C19—C201.500 (3)
C8—C131.377 (2)C20—H20A0.9600
C8—C91.380 (2)C20—H20B0.9600
C9—C101.372 (3)C20—H20C0.9600
C9—H90.9300C21—C221.373 (3)
C10—C111.350 (3)C21—H210.9300
C10—H100.9300C22—H220.9300
C11—C121.350 (3)N1—N21.3686 (19)
C11—F11.362 (2)
C6—C1—C2120.21 (18)C8—C13—H13119.6
C6—C1—H1119.9C12—C13—H13119.6
C2—C1—H1119.9C15—C14—C7102.92 (14)
C3—C2—C1120.67 (18)C15—C14—H14A111.2
C3—C2—H2119.7C7—C14—H14A111.2
C1—C2—H2119.7C15—C14—H14B111.2
C2—C3—C4118.92 (18)C7—C14—H14B111.2
C2—C3—H3120.5H14A—C14—H14B109.1
C4—C3—H3120.5N1—C15—C16121.38 (15)
C3—C4—C5121.39 (19)N1—C15—C14113.20 (15)
C3—C4—H4119.3C16—C15—C14125.41 (15)
C5—C4—H4119.3C17—C16—C22116.93 (16)
C4—C5—C6119.85 (17)C17—C16—C15121.94 (16)
C4—C5—H5120.1C22—C16—C15121.14 (15)
C6—C5—H5120.1C16—C17—C18121.18 (18)
C1—C6—C5118.91 (16)C16—C17—H17119.4
C1—C6—N2120.82 (16)C18—C17—H17119.4
C5—C6—N2120.27 (16)C19—C18—C17121.72 (17)
N2—C7—C8112.84 (15)C19—C18—H18119.1
N2—C7—C14101.54 (14)C17—C18—H18119.1
C8—C7—C14113.54 (15)C18—C19—C21116.80 (17)
N2—C7—H7109.6C18—C19—C20121.65 (17)
C8—C7—H7109.6C21—C19—C20121.55 (19)
C14—C7—H7109.6C19—C20—H20A109.5
C13—C8—C9117.76 (17)C19—C20—H20B109.5
C13—C8—C7122.44 (16)H20A—C20—H20B109.5
C9—C8—C7119.74 (16)C19—C20—H20C109.5
C10—C9—C8121.78 (17)H20A—C20—H20C109.5
C10—C9—H9119.1H20B—C20—H20C109.5
C8—C9—H9119.1C22—C21—C19122.22 (19)
C11—C10—C9118.13 (18)C22—C21—H21118.9
C11—C10—H10120.9C19—C21—H21118.9
C9—C10—H10120.9C21—C22—C16121.15 (17)
C12—C11—C10122.76 (19)C21—C22—H22119.4
C12—C11—F1118.17 (19)C16—C22—H22119.4
C10—C11—F1119.07 (19)C15—N1—N2109.60 (14)
C11—C12—C13118.69 (18)N1—N2—C6119.76 (14)
C11—C12—H12120.7N1—N2—C7112.66 (13)
C13—C12—H12120.7C6—N2—C7124.43 (15)
C8—C13—C12120.87 (18)
C6—C1—C2—C30.4 (3)N1—C15—C16—C17176.97 (15)
C1—C2—C3—C41.3 (3)C14—C15—C16—C174.0 (3)
C2—C3—C4—C51.3 (3)N1—C15—C16—C223.2 (2)
C3—C4—C5—C60.5 (3)C14—C15—C16—C22175.91 (17)
C2—C1—C6—C52.1 (3)C22—C16—C17—C180.7 (3)
C2—C1—C6—N2177.96 (18)C15—C16—C17—C18179.21 (15)
C4—C5—C6—C12.2 (3)C16—C17—C18—C190.5 (3)
C4—C5—C6—N2177.92 (17)C17—C18—C19—C210.2 (3)
N2—C7—C8—C1323.6 (2)C17—C18—C19—C20179.66 (17)
C14—C7—C8—C1391.3 (2)C18—C19—C21—C220.0 (3)
N2—C7—C8—C9159.53 (15)C20—C19—C21—C22179.81 (19)
C14—C7—C8—C985.6 (2)C19—C21—C22—C160.2 (3)
C13—C8—C9—C100.1 (3)C17—C16—C22—C210.5 (3)
C7—C8—C9—C10176.90 (16)C15—C16—C22—C21179.36 (17)
C8—C9—C10—C110.1 (3)C16—C15—N1—N2176.66 (14)
C9—C10—C11—C120.1 (3)C14—C15—N1—N22.50 (19)
C9—C10—C11—F1179.81 (15)C15—N1—N2—C6161.69 (15)
C10—C11—C12—C130.2 (3)C15—N1—N2—C70.88 (19)
F1—C11—C12—C13179.52 (16)C1—C6—N2—N1171.52 (16)
C9—C8—C13—C120.4 (3)C5—C6—N2—N18.6 (3)
C7—C8—C13—C12176.52 (16)C1—C6—N2—C713.1 (3)
C11—C12—C13—C80.5 (3)C5—C6—N2—C7167.00 (16)
N2—C7—C14—C152.16 (18)C8—C7—N2—N1120.91 (15)
C8—C7—C14—C15119.24 (16)C14—C7—N2—N10.97 (19)
C7—C14—C15—N13.0 (2)C8—C7—N2—C679.3 (2)
C7—C14—C15—C16176.13 (14)C14—C7—N2—C6158.79 (16)

Experimental details

Crystal data
Chemical formulaC22H19FN2
Mr330.39
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)14.854 (3), 11.429 (2), 10.833 (2)
β (°) 109.090 (3)
V3)1738.0 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.50 × 0.45 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7135, 3066, 2155
Rint0.020
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.133, 1.02
No. of reflections3066
No. of parameters227
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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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