1-Acetyl-5-(4-fluoro­phen­yl)-3-(4-methyl­phen­yl)-2-pyrazoline

Guo, H.-M.

doi:10.1107/S1600536807038810

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1-Acetyl-5-(4-fluorophenyl)-3-(4-methylphenyl)-2-pyrazoline

H.-M. Guo

In the title compound, C₁₈H₁₇FN₂O, all bond lengths and angles show normal values. The mean plane of pyrazoline ring makes dihedral angles of 83.33 (9) and 17.03 (9)° with the benzene rings; the two benzene rings make a dihedral angle of 76.01 (5)°. The H atoms of both methyl groups are disordered over two positions by rotation about their C—C σ bonds, with occupancies of 0.52 (3) and 0.48 (3) for the methyl of the tolyl group, and 0.62 (2) and 0.38 (2) for the methyl belonging to the acetyl group. Weak intermolecular C—H

F hydrogen bonds connect molecules into centrosymmetric dimers in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038810/bh2115sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038810/bh2115Isup2.hkl Contains datablock I

CCDC reference: 660268

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R factor = 0.040
wR factor = 0.105
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C7     = ...          R

   0 ALERT level A = In general: serious problem
   0 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
   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

Comment top

Pyrazoline and its derivatives are important and useful five-membered heterocyclic compounds, which possess antiviral (Rawal et al., 1963), antifungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Otterness, 1981) activities. 1-Acetyl-3,5-diaryl-2-pyrazoline have also been found to inhibit the monoamine oxidases (Manna et al., 2002). As part of our ongoing investigations on pyrazolines and their metal complexes, we report here the crystal structure of the title compound, (I).

In the structure of (I) (Fig. 1), all bond lengths and angles fall in the normal ranges (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007; Jian et al., 2006). The dihedral angles formed by pyrazolinyl ring with aromatic groups at positions 3 and 5 are 17.03 (1) and 83.33 (2)°, respectively. A weak C—H···F hydrogen bond stabilizes the crystal structure of (I), forming centrosymmetric dimers in the cell.

Related literature top

For related pyrazoline derivatives, see: Fahrni et al. (2003); Guo et al. (2007); Jian et al. (2006); Kimura et al. (1977); Manna et al. (2002); For biological properties, see: Rawal et al. (1963); Dhal et al. (1975); Lombardino & Otterness (1981).

Experimental top

1-(p-Methylphenyl)-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 refluxed for 6 h. Then, the mixture was poured into ice–water to afford colourless solids. The solids were filtrated and washed with water, until the pH of the solution reached 7.0. Finally, the solid product was dried at room temperature. 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 (I), with displacement ellipsoids drawn at the 30% probability level.

1-Acetyl-5-(4-fluorophenyl)-3-(4-methylphenyl)-2-pyrazoline top

Crystal data top

C₁₈H₁₇FN₂O	F(000) = 624
M_r = 296.34	D_x = 1.288 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2013 reflections
a = 14.521 (3) Å	θ = 2.3–24.1°
b = 11.405 (2) Å	µ = 0.09 mm⁻¹
c = 9.719 (2) Å	T = 298 K
β = 108.368 (3)°	Prism, colourless
V = 1527.6 (5) Å³	0.48 × 0.25 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2015 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
φ and ω scans	h = −12→17
6307 measured reflections	k = −13→13
2690 independent reflections	l = −10→11

Refinement top

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) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0477P)² + 0.1686P] where P = (F_o² + 2F_c²)/3
2690 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₁₇FN₂O	V = 1527.6 (5) Å³
M_r = 296.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.521 (3) Å	µ = 0.09 mm⁻¹
b = 11.405 (2) Å	T = 298 K
c = 9.719 (2) Å	0.48 × 0.25 × 0.10 mm
β = 108.368 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2015 reflections with I > 2σ(I)
6307 measured reflections	R_int = 0.023
2690 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	Δρ_max = 0.12 e Å⁻³
2690 reflections	Δρ_min = −0.15 e Å⁻³
203 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.37035 (11)	0.47632 (13)	1.46974 (16)	0.0490 (4)
H1	0.4222	0.4248	1.5039	0.059*
C2	0.32733 (13)	0.52340 (14)	1.56553 (17)	0.0558 (4)
H2	0.3493	0.5039	1.6634	0.067*
C3	0.25217 (14)	0.59881 (15)	1.51273 (19)	0.0586 (4)
C4	0.21734 (13)	0.63002 (16)	1.36947 (19)	0.0643 (5)
H4	0.1657	0.6820	1.3365	0.077*
C5	0.26131 (12)	0.58203 (15)	1.27545 (18)	0.0575 (4)
H5	0.2391	0.6023	1.1778	0.069*
C6	0.33761 (11)	0.50461 (13)	1.32401 (15)	0.0461 (4)
C7	0.38072 (11)	0.44494 (14)	1.21964 (15)	0.0496 (4)
H7	0.4468	0.4182	1.2709	0.059*
C8	0.31881 (12)	0.34222 (14)	1.13874 (16)	0.0522 (4)
H8A	0.3588	0.2750	1.1347	0.063*
H8B	0.2709	0.3192	1.1840	0.063*
C9	0.27163 (11)	0.39268 (13)	0.99076 (16)	0.0463 (4)
C10	0.19172 (11)	0.33801 (13)	0.87748 (16)	0.0471 (4)
C11	0.16780 (12)	0.22164 (15)	0.89026 (19)	0.0569 (4)
H11	0.2009	0.1794	0.9729	0.068*
C12	0.09508 (13)	0.16799 (15)	0.7811 (2)	0.0624 (5)
H12	0.0806	0.0897	0.7915	0.075*
C13	0.04356 (12)	0.22696 (16)	0.65762 (19)	0.0592 (5)
C14	−0.03119 (15)	0.16550 (18)	0.5358 (2)	0.0848 (6)
H14A	−0.0819	0.1358	0.5701	0.127*	0.52 (3)
H14B	−0.0013	0.1016	0.5016	0.127*	0.52 (3)
H14C	−0.0582	0.2198	0.4581	0.127*	0.52 (3)
H14D	−0.0060	0.1538	0.4566	0.127*	0.48 (3)
H14E	−0.0889	0.2125	0.5040	0.127*	0.48 (3)
H14F	−0.0464	0.0909	0.5691	0.127*	0.48 (3)
C15	0.06540 (13)	0.34419 (16)	0.64840 (18)	0.0622 (5)
H15	0.0299	0.3871	0.5677	0.075*
C16	0.13788 (12)	0.39907 (15)	0.75489 (17)	0.0561 (4)
H16	0.1511	0.4778	0.7449	0.067*
C17	0.44121 (12)	0.61308 (14)	1.10642 (18)	0.0518 (4)
C18	0.43325 (13)	0.67838 (15)	0.96995 (19)	0.0650 (5)
H18A	0.4675	0.6365	0.9155	0.098*	0.62 (2)
H18B	0.4609	0.7551	0.9935	0.098*	0.62 (2)
H18C	0.3662	0.6855	0.9131	0.098*	0.62 (2)
H18D	0.4966	0.7028	0.9706	0.098*	0.38 (2)
H18E	0.3927	0.7460	0.9635	0.098*	0.38 (2)
H18F	0.4053	0.6282	0.8881	0.098*	0.38 (2)
F1	0.20957 (9)	0.64612 (10)	1.60668 (12)	0.0882 (4)
N1	0.38063 (10)	0.52101 (11)	1.09674 (13)	0.0512 (3)
N2	0.30906 (9)	0.49040 (12)	0.96894 (13)	0.0502 (3)
O1	0.50015 (9)	0.63776 (11)	1.22326 (13)	0.0713 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0485 (9)	0.0517 (9)	0.0431 (9)	0.0004 (7)	0.0090 (7)	0.0043 (7)
C2	0.0667 (11)	0.0571 (10)	0.0416 (9)	−0.0045 (9)	0.0145 (8)	0.0023 (8)
C3	0.0710 (12)	0.0565 (10)	0.0538 (10)	0.0029 (9)	0.0274 (9)	−0.0033 (8)
C4	0.0642 (11)	0.0663 (11)	0.0613 (11)	0.0185 (9)	0.0183 (9)	0.0058 (9)
C5	0.0570 (10)	0.0689 (11)	0.0430 (9)	0.0092 (9)	0.0104 (8)	0.0071 (8)
C6	0.0433 (8)	0.0507 (9)	0.0406 (8)	−0.0009 (7)	0.0080 (7)	0.0030 (7)
C7	0.0454 (9)	0.0598 (10)	0.0407 (9)	0.0043 (8)	0.0095 (7)	0.0087 (7)
C8	0.0573 (10)	0.0528 (9)	0.0480 (9)	0.0041 (8)	0.0186 (8)	0.0047 (7)
C9	0.0483 (9)	0.0502 (9)	0.0432 (9)	0.0041 (7)	0.0185 (7)	0.0014 (7)
C10	0.0474 (9)	0.0511 (9)	0.0464 (9)	0.0032 (7)	0.0197 (7)	−0.0005 (7)
C11	0.0540 (10)	0.0548 (10)	0.0621 (11)	0.0051 (8)	0.0187 (9)	0.0057 (8)
C12	0.0562 (10)	0.0511 (10)	0.0810 (13)	−0.0020 (9)	0.0234 (10)	−0.0063 (9)
C13	0.0483 (10)	0.0639 (11)	0.0646 (11)	0.0041 (9)	0.0168 (9)	−0.0152 (9)
C14	0.0695 (13)	0.0827 (14)	0.0901 (15)	−0.0002 (11)	0.0077 (11)	−0.0286 (11)
C15	0.0625 (11)	0.0651 (11)	0.0519 (10)	0.0084 (9)	0.0079 (9)	−0.0009 (8)
C16	0.0630 (11)	0.0519 (9)	0.0503 (10)	0.0017 (8)	0.0134 (9)	−0.0004 (8)
C17	0.0482 (9)	0.0555 (10)	0.0525 (10)	0.0011 (8)	0.0170 (8)	−0.0013 (8)
C18	0.0724 (12)	0.0603 (11)	0.0666 (11)	−0.0068 (9)	0.0280 (10)	0.0060 (9)
F1	0.1181 (10)	0.0863 (8)	0.0758 (7)	0.0254 (7)	0.0528 (7)	−0.0003 (6)
N1	0.0514 (8)	0.0606 (8)	0.0396 (7)	−0.0064 (7)	0.0115 (6)	0.0041 (6)
N2	0.0498 (8)	0.0596 (8)	0.0400 (7)	−0.0037 (7)	0.0125 (6)	0.0015 (6)
O1	0.0626 (8)	0.0786 (9)	0.0624 (8)	−0.0137 (7)	0.0051 (7)	−0.0010 (6)

Geometric parameters (Å, º) top

C1—C2	1.383 (2)	C10—C16	1.389 (2)
C1—C6	1.383 (2)	C11—C12	1.382 (2)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.357 (2)	C12—C13	1.373 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—F1	1.3651 (19)	C13—C15	1.383 (2)
C3—C4	1.370 (2)	C13—C14	1.504 (2)
C4—C5	1.382 (2)	C15—C16	1.373 (2)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.379 (2)	C16—H16	0.9300
C5—H5	0.9300	C17—O1	1.2201 (19)
C6—C7	1.511 (2)	C17—N1	1.354 (2)
C7—N1	1.4760 (19)	C17—C18	1.494 (2)
C7—C8	1.534 (2)	N1—N2	1.3897 (17)
C7—H7	0.9800	C14—H14A	0.9600
C8—C9	1.499 (2)	C14—H14B	0.9600
C8—H8A	0.9700	C14—H14C	0.9600
C8—H8B	0.9700	C18—H18A	0.9600
C9—N2	1.2865 (19)	C18—H18B	0.9600
C9—C10	1.464 (2)	C18—H18C	0.9600
C10—C11	1.387 (2)

C2—C1—C6	121.11 (15)	C10—C9—C8	124.91 (14)
C2—C1—H1	119.4	C11—C10—C16	117.86 (15)
C6—C1—H1	119.4	C11—C10—C9	120.11 (14)
C3—C2—C1	118.15 (15)	C16—C10—C9	122.02 (14)
C3—C2—H2	120.9	C12—C11—C10	120.47 (16)
C1—C2—H2	120.9	C12—C11—H11	119.8
C2—C3—F1	118.53 (15)	C10—C11—H11	119.8
C2—C3—C4	122.97 (16)	C13—C12—C11	121.89 (17)
F1—C3—C4	118.50 (16)	C13—C12—H12	119.1
C3—C4—C5	118.00 (16)	C11—C12—H12	119.1
C3—C4—H4	121.0	C12—C13—C15	117.20 (16)
C5—C4—H4	121.0	C12—C13—C14	121.25 (17)
C6—C5—C4	121.08 (15)	C15—C13—C14	121.53 (17)
C6—C5—H5	119.5	C16—C15—C13	121.92 (16)
C4—C5—H5	119.5	C16—C15—H15	119.0
C5—C6—C1	118.68 (15)	C13—C15—H15	119.0
C5—C6—C7	121.12 (13)	C15—C16—C10	120.59 (16)
C1—C6—C7	120.07 (14)	C15—C16—H16	119.7
N1—C7—C6	112.55 (13)	C10—C16—H16	119.7
N1—C7—C8	100.55 (11)	O1—C17—N1	119.57 (15)
C6—C7—C8	112.84 (13)	O1—C17—C18	123.15 (16)
N1—C7—H7	110.2	N1—C17—C18	117.27 (15)
C6—C7—H7	110.2	C17—N1—N2	122.92 (13)
C8—C7—H7	110.2	C17—N1—C7	124.39 (13)
C9—C8—C7	102.44 (12)	N2—N1—C7	112.67 (12)
C9—C8—H8A	111.3	C9—N2—N1	107.82 (12)
C7—C8—H8A	111.3	C13—C14—H14A	109.5
C9—C8—H8B	111.3	C13—C14—H14B	109.5
C7—C8—H8B	111.3	C13—C14—H14C	109.5
H8A—C8—H8B	109.2	C17—C18—H18A	109.5
N2—C9—C10	121.40 (14)	C17—C18—H18B	109.5
N2—C9—C8	113.67 (13)	C17—C18—H18C	109.5

C6—C1—C2—C3	−0.3 (2)	C16—C10—C11—C12	2.5 (2)
C1—C2—C3—F1	−179.69 (15)	C9—C10—C11—C12	−177.35 (15)
C1—C2—C3—C4	0.0 (3)	C10—C11—C12—C13	−0.6 (3)
C2—C3—C4—C5	0.0 (3)	C11—C12—C13—C15	−1.9 (3)
F1—C3—C4—C5	179.70 (16)	C11—C12—C13—C14	176.26 (16)
C3—C4—C5—C6	0.3 (3)	C12—C13—C15—C16	2.5 (3)
C4—C5—C6—C1	−0.6 (2)	C14—C13—C15—C16	−175.68 (17)
C4—C5—C6—C7	175.26 (15)	C13—C15—C16—C10	−0.6 (3)
C2—C1—C6—C5	0.6 (2)	C11—C10—C16—C15	−1.9 (2)
C2—C1—C6—C7	−175.30 (14)	C9—C10—C16—C15	177.90 (15)
C5—C6—C7—N1	35.0 (2)	O1—C17—N1—N2	177.33 (14)
C1—C6—C7—N1	−149.18 (14)	C18—C17—N1—N2	−3.9 (2)
C5—C6—C7—C8	−77.93 (18)	O1—C17—N1—C7	−0.6 (2)
C1—C6—C7—C8	97.86 (17)	C18—C17—N1—C7	178.08 (14)
N1—C7—C8—C9	−15.53 (14)	C6—C7—N1—C17	73.61 (19)
C6—C7—C8—C9	104.59 (14)	C8—C7—N1—C17	−166.07 (14)
C7—C8—C9—N2	12.45 (17)	C6—C7—N1—N2	−104.54 (14)
C7—C8—C9—C10	−168.70 (14)	C8—C7—N1—N2	15.78 (16)
N2—C9—C10—C11	164.88 (15)	C10—C9—N2—N1	178.27 (13)
C8—C9—C10—C11	−13.9 (2)	C8—C9—N2—N1	−2.83 (18)
N2—C9—C10—C16	−14.9 (2)	C17—N1—N2—C9	172.91 (14)
C8—C9—C10—C16	166.30 (15)	C7—N1—N2—C9	−8.90 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14E···F1ⁱ	0.96	2.37	3.314 (2)	166

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇FN₂O
M_r	296.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	14.521 (3), 11.405 (2), 9.719 (2)
β (°)	108.368 (3)
V (Å³)	1527.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.25 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6307, 2690, 2015
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.02
No. of reflections	2690
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.15

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14E···F1ⁱ	0.96	2.37	3.314 (2)	166.4

Symmetry code: (i) −x, −y+1, −z+2.

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