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

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

doi:10.1107/S1600536807024634

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

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

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024634/bh2102sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024634/bh2102Isup2.hkl Contains datablock I

CCDC reference: 651490

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R factor = 0.061
wR factor = 0.222
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =       1.00
            Cell volume su given      =       4.00
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...    1747.00 Ang-3
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C9     = ...          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   5 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
   2 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

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.

Structure description top

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

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

C₂₂H₁₉FN₂	F(000) = 696
M_r = 330.39	D_x = 1.256 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1300 reflections
a = 20.050 (2) Å	θ = 2.5–22.9°
b = 5.588 (3) Å	µ = 0.08 mm⁻¹
c = 16.480 (2) Å	T = 294 K
β = 108.913 (19)°	Block, yellow
V = 1747 (4) Å³	0.30 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3081 independent reflections
Radiation source: fine-focus sealed tube	1371 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
φ and ω scans	θ_max = 25.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −23→23
T_min = 0.976, T_max = 0.984	k = −6→5
8200 measured reflections	l = −16→19

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)] = 0.061	H-atom parameters constrained
wR(F²) = 0.222	w = 1/[σ²(F_o²)] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max < 0.001
3081 reflections	Δρ_max = 0.17 e Å⁻³
228 parameters	Δρ_min = −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: 0.011 (3)

Crystal data top

C₂₂H₁₉FN₂	V = 1747 (4) Å³
M_r = 330.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.050 (2) Å	µ = 0.08 mm⁻¹
b = 5.588 (3) Å	T = 294 K
c = 16.480 (2) Å	0.30 × 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)
T_min = 0.976, T_max = 0.984	R_int = 0.089
8200 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.222	H-atom parameters constrained
S = 0.91	Δρ_max = 0.17 e Å⁻³
3081 reflections	Δρ_min = −0.19 e Å⁻³
228 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.47935 (9)	0.2677 (5)	0.44618 (15)	0.0950 (9)
N1	0.67472 (13)	0.4524 (6)	0.21806 (17)	0.0555 (9)
N2	0.72962 (13)	0.4153 (6)	0.18606 (18)	0.0629 (9)
C1	0.57510 (17)	0.4651 (7)	0.3086 (2)	0.0578 (10)
H1	0.5744	0.5909	0.2714	0.069*
C2	0.52539 (17)	0.4577 (7)	0.3500 (2)	0.0616 (11)
H2	0.4909	0.5754	0.3405	0.074*
C3	0.52810 (16)	0.2733 (8)	0.4051 (2)	0.0640 (12)
C4	0.57658 (18)	0.0955 (8)	0.4198 (2)	0.0663 (11)
H4	0.5765	−0.0293	0.4571	0.080*
C5	0.62618 (17)	0.1041 (7)	0.3778 (2)	0.0576 (10)
H5	0.6601	−0.0156	0.3875	0.069*
C6	0.62597 (15)	0.2896 (7)	0.3213 (2)	0.0505 (9)
C7	0.67859 (15)	0.2964 (7)	0.2776 (2)	0.0505 (9)
C8	0.73981 (17)	0.1281 (7)	0.2917 (2)	0.0621 (11)
H8A	0.7238	−0.0321	0.2721	0.074*
H8B	0.7682	0.1217	0.3518	0.074*
C9	0.78135 (16)	0.2389 (7)	0.2373 (2)	0.0564 (10)
H9	0.7900	0.1168	0.1992	0.068*
C10	0.85006 (16)	0.3557 (7)	0.2878 (2)	0.0541 (10)
C11	0.91418 (18)	0.2616 (7)	0.2897 (2)	0.0645 (11)
H11	0.9154	0.1203	0.2604	0.077*
C12	0.97669 (19)	0.3746 (9)	0.3345 (3)	0.0728 (13)
H12	1.0192	0.3065	0.3351	0.087*
C13	0.97758 (19)	0.5875 (8)	0.3786 (2)	0.0674 (12)
C14	0.91340 (19)	0.6792 (8)	0.3770 (2)	0.0700 (11)
H14	0.9122	0.8205	0.4063	0.084*
C15	0.85109 (19)	0.5671 (8)	0.3333 (2)	0.0629 (11)
H15	0.8087	0.6336	0.3339	0.075*
C16	1.04571 (19)	0.7126 (9)	0.4272 (3)	0.0934 (15)
H16A	1.0464	0.8690	0.4033	0.140*
H16B	1.0849	0.6210	0.4227	0.140*
H16C	1.0492	0.7273	0.4865	0.140*
C17	0.73954 (16)	0.5733 (7)	0.1260 (2)	0.0510 (10)
C18	0.79532 (18)	0.5398 (8)	0.0943 (2)	0.0677 (12)
H18	0.8257	0.4106	0.1129	0.081*
C19	0.80556 (19)	0.6973 (9)	0.0355 (2)	0.0763 (13)
H19	0.8439	0.6755	0.0162	0.092*
C20	0.76105 (19)	0.8849 (9)	0.0048 (2)	0.0723 (12)
H20	0.7683	0.9895	−0.0354	0.087*
C21	0.70498 (17)	0.9152 (8)	0.0348 (2)	0.0686 (12)
H21	0.6739	1.0415	0.0140	0.082*
C22	0.69399 (16)	0.7640 (7)	0.0945 (2)	0.0572 (11)
H22	0.6559	0.7888	0.1140	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0643 (13)	0.129 (2)	0.1097 (19)	−0.0038 (14)	0.0529 (13)	0.0221 (16)
N1	0.0469 (15)	0.075 (2)	0.0486 (17)	0.0069 (16)	0.0208 (14)	0.0043 (17)
N2	0.0556 (16)	0.082 (2)	0.0600 (18)	0.0223 (17)	0.0312 (15)	0.0262 (18)
C1	0.0478 (19)	0.073 (3)	0.051 (2)	0.000 (2)	0.0143 (18)	0.008 (2)
C2	0.0445 (19)	0.080 (3)	0.060 (2)	0.004 (2)	0.0172 (18)	0.002 (2)
C3	0.0378 (18)	0.100 (4)	0.058 (2)	−0.014 (2)	0.0207 (18)	0.004 (2)
C4	0.053 (2)	0.084 (3)	0.065 (2)	−0.013 (2)	0.023 (2)	0.014 (2)
C5	0.0502 (19)	0.066 (3)	0.058 (2)	−0.006 (2)	0.0187 (18)	0.005 (2)
C6	0.0395 (17)	0.068 (3)	0.0424 (18)	−0.0103 (19)	0.0103 (15)	−0.003 (2)
C7	0.0457 (18)	0.066 (3)	0.0413 (18)	0.0001 (19)	0.0157 (16)	0.002 (2)
C8	0.059 (2)	0.068 (3)	0.063 (2)	0.004 (2)	0.0263 (18)	0.005 (2)
C9	0.056 (2)	0.065 (3)	0.055 (2)	0.012 (2)	0.0271 (18)	0.011 (2)
C10	0.053 (2)	0.065 (3)	0.052 (2)	0.010 (2)	0.0276 (18)	0.011 (2)
C11	0.061 (2)	0.069 (3)	0.073 (3)	0.010 (2)	0.035 (2)	0.003 (2)
C12	0.057 (2)	0.087 (4)	0.083 (3)	0.012 (2)	0.035 (2)	0.020 (3)
C13	0.066 (2)	0.081 (3)	0.062 (2)	−0.004 (3)	0.031 (2)	0.015 (2)
C14	0.074 (3)	0.073 (3)	0.071 (3)	−0.004 (2)	0.035 (2)	−0.002 (2)
C15	0.061 (2)	0.069 (3)	0.067 (2)	0.011 (2)	0.031 (2)	0.004 (2)
C16	0.077 (3)	0.111 (4)	0.093 (3)	−0.022 (3)	0.028 (2)	0.014 (3)
C17	0.0434 (18)	0.071 (3)	0.0363 (18)	0.0020 (19)	0.0091 (16)	0.0070 (19)
C18	0.064 (2)	0.090 (3)	0.057 (2)	0.014 (2)	0.030 (2)	0.017 (2)
C19	0.058 (2)	0.119 (4)	0.057 (2)	0.007 (3)	0.026 (2)	0.015 (3)
C20	0.062 (2)	0.103 (4)	0.053 (2)	−0.006 (3)	0.019 (2)	0.022 (2)
C21	0.056 (2)	0.084 (3)	0.059 (2)	0.002 (2)	0.0089 (19)	0.020 (2)
C22	0.0396 (18)	0.080 (3)	0.048 (2)	0.001 (2)	0.0085 (16)	0.009 (2)

Geometric parameters (Å, º) top

F1—C3	1.358 (4)	C11—C12	1.384 (5)
N1—C7	1.296 (4)	C11—H11	0.9300
N1—N2	1.382 (3)	C12—C13	1.392 (6)
N2—C17	1.388 (4)	C12—H12	0.9300
N2—C9	1.481 (4)	C13—C14	1.377 (5)
C1—C2	1.378 (4)	C13—C16	1.512 (5)
C1—C6	1.381 (5)	C14—C15	1.375 (5)
C1—H1	0.9300	C14—H14	0.9300
C2—C3	1.363 (5)	C15—H15	0.9300
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.356 (5)	C16—H16B	0.9600
C4—C5	1.384 (4)	C16—H16C	0.9600
C4—H4	0.9300	C17—C22	1.390 (5)
C5—C6	1.392 (5)	C17—C18	1.392 (4)
C5—H5	0.9300	C18—C19	1.373 (5)
C6—C7	1.459 (4)	C18—H18	0.9300
C7—C8	1.503 (5)	C19—C20	1.363 (6)
C8—C9	1.538 (4)	C19—H19	0.9300
C8—H8A	0.9700	C20—C21	1.377 (5)
C8—H8B	0.9700	C20—H20	0.9300
C9—C10	1.508 (5)	C21—C22	1.368 (5)
C9—H9	0.9800	C21—H21	0.9300
C10—C11	1.380 (5)	C22—H22	0.9300
C10—C15	1.395 (5)

C7—N1—N2	109.2 (3)	C10—C11—C12	120.9 (4)
N1—N2—C17	119.5 (3)	C10—C11—H11	119.5
N1—N2—C9	112.3 (3)	C12—C11—H11	119.5
C17—N2—C9	126.5 (3)	C11—C12—C13	121.7 (4)
C2—C1—C6	121.4 (3)	C11—C12—H12	119.2
C2—C1—H1	119.3	C13—C12—H12	119.2
C6—C1—H1	119.3	C14—C13—C12	117.0 (4)
C3—C2—C1	118.3 (3)	C14—C13—C16	121.1 (4)
C3—C2—H2	120.9	C12—C13—C16	121.9 (4)
C1—C2—H2	120.9	C15—C14—C13	121.7 (4)
C4—C3—F1	119.0 (4)	C15—C14—H14	119.2
C4—C3—C2	122.9 (3)	C13—C14—H14	119.2
F1—C3—C2	118.1 (4)	C14—C15—C10	121.4 (3)
C3—C4—C5	118.4 (4)	C14—C15—H15	119.3
C3—C4—H4	120.8	C10—C15—H15	119.3
C5—C4—H4	120.8	C13—C16—H16A	109.5
C4—C5—C6	120.9 (4)	C13—C16—H16B	109.5
C4—C5—H5	119.6	H16A—C16—H16B	109.5
C6—C5—H5	119.6	C13—C16—H16C	109.5
C1—C6—C5	118.2 (3)	H16A—C16—H16C	109.5
C1—C6—C7	121.6 (3)	H16B—C16—H16C	109.5
C5—C6—C7	120.3 (3)	N2—C17—C22	121.7 (3)
N1—C7—C6	121.1 (3)	N2—C17—C18	120.0 (3)
N1—C7—C8	112.6 (3)	C22—C17—C18	118.2 (3)
C6—C7—C8	126.3 (3)	C19—C18—C17	120.1 (4)
C7—C8—C9	103.1 (3)	C19—C18—H18	120.0
C7—C8—H8A	111.1	C17—C18—H18	120.0
C9—C8—H8A	111.1	C20—C19—C18	121.7 (3)
C7—C8—H8B	111.1	C20—C19—H19	119.1
C9—C8—H8B	111.1	C18—C19—H19	119.1
H8A—C8—H8B	109.1	C19—C20—C21	118.3 (3)
N2—C9—C10	111.9 (3)	C19—C20—H20	120.9
N2—C9—C8	100.9 (2)	C21—C20—H20	120.9
C10—C9—C8	115.0 (3)	C22—C21—C20	121.5 (4)
N2—C9—H9	109.6	C22—C21—H21	119.2
C10—C9—H9	109.6	C20—C21—H21	119.2
C8—C9—H9	109.6	C21—C22—C17	120.2 (3)
C11—C10—C15	117.3 (3)	C21—C22—H22	119.9
C11—C10—C9	121.7 (3)	C17—C22—H22	119.9
C15—C10—C9	121.0 (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—C11	112.0 (4)
C6—C1—C2—C3	0.9 (5)	N2—C9—C10—C15	44.9 (4)
C1—C2—C3—C4	−1.2 (6)	C8—C9—C10—C15	−69.4 (4)
C1—C2—C3—F1	179.5 (3)	C15—C10—C11—C12	−0.4 (5)
F1—C3—C4—C5	−179.7 (3)	C9—C10—C11—C12	178.3 (3)
C2—C3—C4—C5	1.1 (6)	C10—C11—C12—C13	−0.6 (6)
C3—C4—C5—C6	−0.6 (5)	C11—C12—C13—C14	1.1 (6)
C2—C1—C6—C5	−0.4 (5)	C11—C12—C13—C16	−179.6 (3)
C2—C1—C6—C7	179.9 (3)	C12—C13—C14—C15	−0.6 (6)
C4—C5—C6—C1	0.3 (5)	C16—C13—C14—C15	−179.9 (3)
C4—C5—C6—C7	180.0 (3)	C13—C14—C15—C10	−0.5 (6)
N2—N1—C7—C6	−178.4 (3)	C11—C10—C15—C14	1.0 (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—N1	172.5 (3)	C9—N2—C17—C22	−166.4 (3)
C1—C6—C7—C8	174.6 (3)	N1—N2—C17—C18	179.0 (3)
C5—C6—C7—C8	−5.1 (5)	C9—N2—C17—C18	15.1 (5)
N1—C7—C8—C9	8.9 (4)	N2—C17—C18—C19	−179.4 (4)
C6—C7—C8—C9	−173.3 (3)	C22—C17—C18—C19	2.1 (5)
N1—N2—C9—C10	−109.1 (3)	C17—C18—C19—C20	−1.9 (6)
C17—N2—C9—C10	55.8 (4)	C18—C19—C20—C21	0.5 (6)
N1—N2—C9—C8	13.7 (4)	C19—C20—C21—C22	0.6 (6)
C17—N2—C9—C8	178.6 (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—C10	108.0 (3)	C18—C17—C22—C21	−0.9 (5)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉FN₂
M_r	330.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	20.050 (2), 5.588 (3), 16.480 (2)
β (°)	108.913 (19)
V (Å³)	1747 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.976, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8200, 3081, 1371
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.222, 0.91
No. of reflections	3081
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −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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