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Acta Cryst. (2007). E63, o3779    [ doi:10.1107/S1600536807038810 ]

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

H.-M. Guo

Abstract top

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 [sigma] 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.

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.

Refinement top

In the case of methyl groups, a difference map revealed that H atoms are disordered over two positions, by rotation about the C—C bonds. In the last refinement cycles, corresponding H positions were regularized, with C—H bond lengths set to 0.96 Å. Site occupation factors of H atoms were refined to 0.52 (3)/0.48 (3) for the methyl of the tolyl group and 0.62 (2)/0.38 (2) for the methyl belonging to the acetyl group. Other H atoms were placed geometrically and allowed to ride on their parent atoms, with C—H distances set to 0.93 (aromatic CH), 0.97 (methylene CH2) and 0.98 Å (methine CH). In all cases, isotropic displacement parameters for H atoms were set to Uiso(H) = xUeq(carrier C atom), with x = 1.5 for methyl groups and x = 1.2 otherwise.

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.
1-Acetyl-5-(4-fluorophenyl)-3-(4-methylphenyl)-2-pyrazoline top
Crystal data top
C18H17FN2OF000 = 624
Mr = 296.34Dx = 1.288 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2013 reflections
a = 14.521 (3) Åθ = 2.3–24.1º
b = 11.405 (2) ŵ = 0.09 mm−1
c = 9.719 (2) ÅT = 298 (2) K
β = 108.368 (3)ºPrism, colourless
V = 1527.6 (5) Å30.48 × 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 tubeRint = 0.023
Monochromator: graphiteθmax = 25.0º
T = 298(2) Kθmin = 2.3º
φ and ω scansh = −12→17
Absorption correction: nonek = −13→13
6307 measured reflectionsl = −10→11
2690 independent reflections
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.105  w = 1/[σ2(Fo2) + (0.0477P)2 + 0.1686P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2690 reflectionsΔρmax = 0.12 e Å−3
203 parametersΔρmin = −0.15 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C18H17FN2OV = 1527.6 (5) Å3
Mr = 296.34Z = 4
Monoclinic, P21/cMo Kα
a = 14.521 (3) ŵ = 0.09 mm−1
b = 11.405 (2) ÅT = 298 (2) K
c = 9.719 (2) Å0.48 × 0.25 × 0.10 mm
β = 108.368 (3)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		2690 independent reflections
Absorption correction: none2015 reflections with I > 2σ(I)
6307 measured reflectionsRint = 0.023
Refinement top
R[F2 > 2σ(F2)] = 0.040203 parameters
wR(F2) = 0.105H-atom parameters constrained
S = 1.02Δρmax = 0.12 e Å−3
2690 reflectionsΔρmin = −0.15 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.37035 (11)0.47632 (13)1.46974 (16)0.0490 (4)
H10.42220.42481.50390.059*
C20.32733 (13)0.52340 (14)1.56553 (17)0.0558 (4)
H20.34930.50391.66340.067*
C30.25217 (14)0.59881 (15)1.51273 (19)0.0586 (4)
C40.21734 (13)0.63002 (16)1.36947 (19)0.0643 (5)
H40.16570.68201.33650.077*
C50.26131 (12)0.58203 (15)1.27545 (18)0.0575 (4)
H50.23910.60231.17780.069*
C60.33761 (11)0.50461 (13)1.32401 (15)0.0461 (4)
C70.38072 (11)0.44494 (14)1.21964 (15)0.0496 (4)
H70.44680.41821.27090.059*
C80.31881 (12)0.34222 (14)1.13874 (16)0.0522 (4)
H8A0.35880.27501.13470.063*
H8B0.27090.31921.18400.063*
C90.27163 (11)0.39268 (13)0.99076 (16)0.0463 (4)
C100.19172 (11)0.33801 (13)0.87748 (16)0.0471 (4)
C110.16780 (12)0.22164 (15)0.89026 (19)0.0569 (4)
H110.20090.17940.97290.068*
C120.09508 (13)0.16799 (15)0.7811 (2)0.0624 (5)
H120.08060.08970.79150.075*
C130.04356 (12)0.22696 (16)0.65762 (19)0.0592 (5)
C14−0.03119 (15)0.16550 (18)0.5358 (2)0.0848 (6)
H14A−0.08190.13580.57010.127*0.52 (3)
H14B−0.00130.10160.50160.127*0.52 (3)
H14C−0.05820.21980.45810.127*0.52 (3)
H14D−0.00600.15380.45660.127*0.48 (3)
H14E−0.08890.21250.50400.127*0.48 (3)
H14F−0.04640.09090.56910.127*0.48 (3)
C150.06540 (13)0.34419 (16)0.64840 (18)0.0622 (5)
H150.02990.38710.56770.075*
C160.13788 (12)0.39907 (15)0.75489 (17)0.0561 (4)
H160.15110.47780.74490.067*
C170.44121 (12)0.61308 (14)1.10642 (18)0.0518 (4)
C180.43325 (13)0.67838 (15)0.96995 (19)0.0650 (5)
H18A0.46750.63650.91550.098*0.62 (2)
H18B0.46090.75510.99350.098*0.62 (2)
H18C0.36620.68550.91310.098*0.62 (2)
H18D0.49660.70280.97060.098*0.38 (2)
H18E0.39270.74600.96350.098*0.38 (2)
H18F0.40530.62820.88810.098*0.38 (2)
F10.20957 (9)0.64612 (10)1.60668 (12)0.0882 (4)
N10.38063 (10)0.52101 (11)1.09674 (13)0.0512 (3)
N20.30906 (9)0.49040 (12)0.96894 (13)0.0502 (3)
O10.50015 (9)0.63776 (11)1.22326 (13)0.0713 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0485 (9)0.0517 (9)0.0431 (9)0.0004 (7)0.0090 (7)0.0043 (7)
C20.0667 (11)0.0571 (10)0.0416 (9)−0.0045 (9)0.0145 (8)0.0023 (8)
C30.0710 (12)0.0565 (10)0.0538 (10)0.0029 (9)0.0274 (9)−0.0033 (8)
C40.0642 (11)0.0663 (11)0.0613 (11)0.0185 (9)0.0183 (9)0.0058 (9)
C50.0570 (10)0.0689 (11)0.0430 (9)0.0092 (9)0.0104 (8)0.0071 (8)
C60.0433 (8)0.0507 (9)0.0406 (8)−0.0009 (7)0.0080 (7)0.0030 (7)
C70.0454 (9)0.0598 (10)0.0407 (9)0.0043 (8)0.0095 (7)0.0087 (7)
C80.0573 (10)0.0528 (9)0.0480 (9)0.0041 (8)0.0186 (8)0.0047 (7)
C90.0483 (9)0.0502 (9)0.0432 (9)0.0041 (7)0.0185 (7)0.0014 (7)
C100.0474 (9)0.0511 (9)0.0464 (9)0.0032 (7)0.0197 (7)−0.0005 (7)
C110.0540 (10)0.0548 (10)0.0621 (11)0.0051 (8)0.0187 (9)0.0057 (8)
C120.0562 (10)0.0511 (10)0.0810 (13)−0.0020 (9)0.0234 (10)−0.0063 (9)
C130.0483 (10)0.0639 (11)0.0646 (11)0.0041 (9)0.0168 (9)−0.0152 (9)
C140.0695 (13)0.0827 (14)0.0901 (15)−0.0002 (11)0.0077 (11)−0.0286 (11)
C150.0625 (11)0.0651 (11)0.0519 (10)0.0084 (9)0.0079 (9)−0.0009 (8)
C160.0630 (11)0.0519 (9)0.0503 (10)0.0017 (8)0.0134 (9)−0.0004 (8)
C170.0482 (9)0.0555 (10)0.0525 (10)0.0011 (8)0.0170 (8)−0.0013 (8)
C180.0724 (12)0.0603 (11)0.0666 (11)−0.0068 (9)0.0280 (10)0.0060 (9)
F10.1181 (10)0.0863 (8)0.0758 (7)0.0254 (7)0.0528 (7)−0.0003 (6)
N10.0514 (8)0.0606 (8)0.0396 (7)−0.0064 (7)0.0115 (6)0.0041 (6)
N20.0498 (8)0.0596 (8)0.0400 (7)−0.0037 (7)0.0125 (6)0.0015 (6)
O10.0626 (8)0.0786 (9)0.0624 (8)−0.0137 (7)0.0051 (7)−0.0010 (6)
Geometric parameters (Å, °) top
C1—C21.383 (2)C10—C161.389 (2)
C1—C61.383 (2)C11—C121.382 (2)
C1—H10.9300C11—H110.9300
C2—C31.357 (2)C12—C131.373 (2)
C2—H20.9300C12—H120.9300
C3—F11.3651 (19)C13—C151.383 (2)
C3—C41.370 (2)C13—C141.504 (2)
C4—C51.382 (2)C15—C161.373 (2)
C4—H40.9300C15—H150.9300
C5—C61.379 (2)C16—H160.9300
C5—H50.9300C17—O11.2201 (19)
C6—C71.511 (2)C17—N11.354 (2)
C7—N11.4760 (19)C17—C181.494 (2)
C7—C81.534 (2)N1—N21.3897 (17)
C7—H70.9800C14—H14A0.9600
C8—C91.499 (2)C14—H14B0.9600
C8—H8A0.9700C14—H14C0.9600
C8—H8B0.9700C18—H18A0.9600
C9—N21.2865 (19)C18—H18B0.9600
C9—C101.464 (2)C18—H18C0.9600
C10—C111.387 (2)
C2—C1—C6121.11 (15)C10—C9—C8124.91 (14)
C2—C1—H1119.4C11—C10—C16117.86 (15)
C6—C1—H1119.4C11—C10—C9120.11 (14)
C3—C2—C1118.15 (15)C16—C10—C9122.02 (14)
C3—C2—H2120.9C12—C11—C10120.47 (16)
C1—C2—H2120.9C12—C11—H11119.8
C2—C3—F1118.53 (15)C10—C11—H11119.8
C2—C3—C4122.97 (16)C13—C12—C11121.89 (17)
F1—C3—C4118.50 (16)C13—C12—H12119.1
C3—C4—C5118.00 (16)C11—C12—H12119.1
C3—C4—H4121.0C12—C13—C15117.20 (16)
C5—C4—H4121.0C12—C13—C14121.25 (17)
C6—C5—C4121.08 (15)C15—C13—C14121.53 (17)
C6—C5—H5119.5C16—C15—C13121.92 (16)
C4—C5—H5119.5C16—C15—H15119.0
C5—C6—C1118.68 (15)C13—C15—H15119.0
C5—C6—C7121.12 (13)C15—C16—C10120.59 (16)
C1—C6—C7120.07 (14)C15—C16—H16119.7
N1—C7—C6112.55 (13)C10—C16—H16119.7
N1—C7—C8100.55 (11)O1—C17—N1119.57 (15)
C6—C7—C8112.84 (13)O1—C17—C18123.15 (16)
N1—C7—H7110.2N1—C17—C18117.27 (15)
C6—C7—H7110.2C17—N1—N2122.92 (13)
C8—C7—H7110.2C17—N1—C7124.39 (13)
C9—C8—C7102.44 (12)N2—N1—C7112.67 (12)
C9—C8—H8A111.3C9—N2—N1107.82 (12)
C7—C8—H8A111.3C13—C14—H14A109.5
C9—C8—H8B111.3C13—C14—H14B109.5
C7—C8—H8B111.3C13—C14—H14C109.5
H8A—C8—H8B109.2C17—C18—H18A109.5
N2—C9—C10121.40 (14)C17—C18—H18B109.5
N2—C9—C8113.67 (13)C17—C18—H18C109.5
C6—C1—C2—C3−0.3 (2)C16—C10—C11—C122.5 (2)
C1—C2—C3—F1−179.69 (15)C9—C10—C11—C12−177.35 (15)
C1—C2—C3—C40.0 (3)C10—C11—C12—C13−0.6 (3)
C2—C3—C4—C50.0 (3)C11—C12—C13—C15−1.9 (3)
F1—C3—C4—C5179.70 (16)C11—C12—C13—C14176.26 (16)
C3—C4—C5—C60.3 (3)C12—C13—C15—C162.5 (3)
C4—C5—C6—C1−0.6 (2)C14—C13—C15—C16−175.68 (17)
C4—C5—C6—C7175.26 (15)C13—C15—C16—C10−0.6 (3)
C2—C1—C6—C50.6 (2)C11—C10—C16—C15−1.9 (2)
C2—C1—C6—C7−175.30 (14)C9—C10—C16—C15177.90 (15)
C5—C6—C7—N135.0 (2)O1—C17—N1—N2177.33 (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—C897.86 (17)C18—C17—N1—C7178.08 (14)
N1—C7—C8—C9−15.53 (14)C6—C7—N1—C1773.61 (19)
C6—C7—C8—C9104.59 (14)C8—C7—N1—C17−166.07 (14)
C7—C8—C9—N212.45 (17)C6—C7—N1—N2−104.54 (14)
C7—C8—C9—C10−168.70 (14)C8—C7—N1—N215.78 (16)
N2—C9—C10—C11164.88 (15)C10—C9—N2—N1178.27 (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—C9172.91 (14)
C8—C9—C10—C16166.30 (15)C7—N1—N2—C9−8.90 (17)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C14—H14E···F1i0.962.373.314 (2)166
Symmetry codes: (i) −x, −y+1, −z+2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C14—H14E···F1i0.962.373.314 (2)166
Symmetry codes: (i) −x, −y+1, −z+2.
references
References top

Bruker (1997). SMART (Version 5.044), SAINT (Version 5.01) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.

Dhal, P. N., Achary, T. E. & Nayak, A. (1975). J. Indian Chem. Soc. 52, 1196–1199.

Fahrni, C. J., Yang, L. & VanDerveer, D. G. (2003). J. Am. Chem. Soc. 125, 3799–3812.

Guo, H.-M., Jian, F.-F., Zhao, P.-S., Sun, X.-Z. & Lin, C.-H. (2007). Acta Cryst. E63, o2618–o2619.

Jian, F.-F., Wang, J. & Xiao, H.-L. (2006). Acta Cryst. E62, o4771–o4772.

Kimura, T., Kai, Y., Yasuoka, N. & Kasai, N. (1977). Acta Cryst. B33, 1786–1792.

Lombardino, J. G. & Otterness, I. G. (1981). J. Med. Chem. 24, 830–834.

Manna, F., Chimenti, F., Bolasco, A., Secci, D., Bizzarri, B., Befani, O., Turini, P., Mondovi, B., Alcaro, S. & Tafi, A. (2002). Bioorg. Med. Chem. Lett. 12, 3629–3633.

Rawal, A. A., Thakor, V. M. & Shah, N. M. (1963). J. Indian Chem. Soc. 40, 323–326.

Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.