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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1391.
Published online 2008 July 5. doi:  10.1107/S1600536808018333
PMCID: PMC2962024

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

Abstract

In the title mol­ecule, C17H14ClFN2O, the mean plane of the pyrazoline ring makes dihedral angles of 18.19 (1) and 83.51 (4)° with the 4-chloro­benzene and 4-fluoro­benzene rings, respectively. The two benzene rings make a dihedral angle of 76.11 (2)°. Weak inter­molecular C—H(...)O hydrogen bonds help stabilize the crystal structure.

Related literature

For related literature, see: Dhal et al. (1975 [triangle]); Fahrni et al. (2003 [triangle]); Kimura et al. (1977 [triangle]); Lombardino & Ottemes (1981 [triangle]); Manna et al. (2002 [triangle]); Rawal et al. (1963 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1391-scheme1.jpg

Experimental

Crystal data

  • C17H14ClFN2O
  • M r = 316.75
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1391-efi1.jpg
  • a = 14.5425 (19) Å
  • b = 11.3580 (14) Å
  • c = 9.6494 (13) Å
  • β = 108.154 (2)°
  • V = 1514.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 273 (2) K
  • 0.14 × 0.12 × 0.06 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 7793 measured reflections
  • 2676 independent reflections
  • 2077 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.098
  • S = 1.03
  • 2676 reflections
  • 200 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018333/at2570sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018333/at2570Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Sparking Plan of Shandong Province (grant No. 200674006017) and the National Sparking Plan Project (grant No. 2007E740083).

supplementary crystallographic information

Comment

Pyrazoline and some of its derivatives demonstrate antiviral (Rawal et al., 1963), antifungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. 1-Acetyl-3,5-diaryl-2-pyrazolines have been found to inhibit monoamine oxidases (Manna et al., 2002). As part of our ongoing investigation of pyrazolines and their metal complexes, we report here the crystal structure of the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal (Fahrni et al., 2003; Kimura et al., 1977). The mean plane of pyrazoline ring makes dihedral angles of 18.19 (1)° and 83.51 (4)° with 4-chlorobenzene ring and 4-fluorolbenzene ring, respectively. The dihedral angle between the two benzene rings is 76.11 (2)°. Weak intermolecular C—H···O hydrogen bonds help stabilize the crystal structure (Table 1). The crystal packing of (I) is shown in Fig. 2.

Experimental

1-(4-chlorophenyl)-3-(4-fluorophenyl)-2-propenyl-1-ketone (0.02 mol)and hydrazine (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 colourless 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

H atoms were fixed geometrically and allowed to ride on their parent atoms, with C—H distances of 0.93–0.976 Å, and with Uiso=1.2–1.5Ueq of the parent atoms.

Figures

Fig. 1.
The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
View of the crysytal packing of (I) in the unit cell.

Crystal data

C17H14ClFN2OF000 = 656
Mr = 316.75Dx = 1.389 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2887 reflections
a = 14.5425 (19) Åθ = 2.9–25.9º
b = 11.3580 (14) ŵ = 0.27 mm1
c = 9.6494 (13) ÅT = 273 (2) K
β = 108.154 (2)ºBar, colourless
V = 1514.5 (3) Å30.14 × 0.12 × 0.06 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2077 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Monochromator: graphiteθmax = 25.1º
T = 273(2) Kθmin = 2.3º
[var phi] and ω scansh = −17→17
Absorption correction: nonek = −13→11
7793 measured reflectionsl = −11→9
2676 independent reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037  w = 1/[σ2(Fo2) + (0.0385P)2 + 0.4849P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.20 e Å3
2676 reflectionsΔρmin = −0.21 e Å3
200 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0031 (10)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
Cl10.45884 (5)0.34606 (6)0.02764 (8)0.0949 (3)
F10.70769 (11)−0.14714 (11)1.10898 (14)0.0851 (4)
O11.00066 (10)−0.13914 (13)0.72130 (15)0.0685 (4)
N10.88095 (10)−0.02205 (13)0.59652 (15)0.0491 (4)
N20.80952 (10)0.00960 (13)0.46876 (15)0.0477 (4)
C10.93307 (15)−0.17908 (18)0.4668 (2)0.0610 (5)
H1A0.9661−0.13610.41090.092*
H1B0.8660−0.18730.41110.092*
H1C0.9617−0.25570.48980.092*
C20.94144 (13)−0.11419 (16)0.6044 (2)0.0494 (4)
C30.88134 (13)0.05353 (16)0.72122 (18)0.0477 (4)
H30.94740.07970.77300.057*
C40.82018 (14)0.15743 (16)0.64155 (19)0.0500 (5)
H4A0.77280.18080.68810.060*
H4B0.86040.22460.63730.060*
C50.77233 (12)0.10719 (16)0.49247 (18)0.0454 (4)
C60.83785 (12)−0.00700 (15)0.82540 (18)0.0446 (4)
C70.76197 (13)−0.08590 (17)0.7766 (2)0.0530 (5)
H70.7404−0.10700.67860.064*
C80.71794 (15)−0.13366 (18)0.8711 (2)0.0593 (5)
H80.6671−0.18680.83820.071*
C90.75105 (15)−0.10081 (18)1.0151 (2)0.0574 (5)
C100.82613 (14)−0.02457 (17)1.0681 (2)0.0537 (5)
H100.8474−0.00441.16640.064*
C110.86977 (13)0.02200 (16)0.97206 (18)0.0481 (4)
H110.92150.07371.00650.058*
C120.69236 (12)0.16303 (16)0.37998 (19)0.0455 (4)
C130.63734 (14)0.10150 (18)0.2576 (2)0.0557 (5)
H130.64990.02220.24730.067*
C140.56443 (15)0.15720 (19)0.1515 (2)0.0621 (5)
H140.52750.11540.07030.075*
C150.54634 (13)0.27427 (18)0.1657 (2)0.0588 (5)
C160.59780 (14)0.33572 (18)0.2860 (3)0.0630 (6)
H160.58420.41470.29570.076*
C170.67020 (14)0.28007 (17)0.3936 (2)0.0558 (5)
H170.70460.32180.47640.067*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0695 (4)0.0900 (5)0.1055 (5)0.0056 (3)−0.0012 (3)0.0364 (4)
F10.1184 (11)0.0792 (9)0.0750 (9)−0.0204 (8)0.0552 (8)0.0010 (7)
O10.0622 (9)0.0758 (10)0.0578 (9)0.0125 (7)0.0045 (7)0.0014 (7)
N10.0505 (8)0.0581 (9)0.0370 (8)0.0056 (7)0.0111 (7)−0.0052 (7)
N20.0485 (8)0.0565 (9)0.0372 (8)0.0015 (7)0.0121 (6)−0.0026 (7)
C10.0680 (13)0.0577 (12)0.0615 (12)0.0051 (10)0.0261 (10)−0.0078 (10)
C20.0464 (10)0.0528 (11)0.0501 (11)−0.0025 (9)0.0167 (9)0.0005 (9)
C30.0456 (10)0.0571 (11)0.0393 (9)−0.0055 (8)0.0115 (8)−0.0086 (8)
C40.0573 (11)0.0502 (11)0.0437 (10)−0.0045 (9)0.0177 (8)−0.0045 (8)
C50.0474 (10)0.0504 (11)0.0413 (9)−0.0051 (8)0.0180 (8)−0.0026 (8)
C60.0431 (9)0.0497 (10)0.0381 (9)0.0034 (8)0.0084 (7)−0.0024 (8)
C70.0529 (11)0.0613 (12)0.0416 (10)−0.0062 (9)0.0098 (8)−0.0067 (9)
C80.0599 (12)0.0570 (12)0.0623 (13)−0.0115 (10)0.0209 (10)−0.0044 (10)
C90.0710 (13)0.0546 (12)0.0542 (12)0.0017 (10)0.0302 (10)0.0049 (9)
C100.0666 (12)0.0541 (11)0.0388 (10)0.0037 (10)0.0142 (9)−0.0018 (8)
C110.0487 (10)0.0498 (10)0.0416 (10)0.0001 (8)0.0078 (8)−0.0043 (8)
C120.0452 (10)0.0504 (11)0.0441 (10)−0.0035 (8)0.0188 (8)0.0003 (8)
C130.0609 (12)0.0519 (11)0.0513 (11)−0.0008 (9)0.0131 (9)−0.0012 (9)
C140.0592 (12)0.0677 (14)0.0526 (12)−0.0076 (10)0.0075 (10)0.0003 (10)
C150.0450 (11)0.0608 (13)0.0685 (13)−0.0036 (9)0.0144 (9)0.0141 (10)
C160.0534 (12)0.0488 (11)0.0880 (16)0.0000 (9)0.0238 (11)0.0063 (11)
C170.0511 (11)0.0532 (12)0.0636 (12)−0.0058 (9)0.0183 (10)−0.0062 (10)

Geometric parameters (Å, °)

Cl1—C151.733 (2)C6—C71.385 (2)
F1—C91.361 (2)C7—C81.378 (3)
O1—C21.220 (2)C7—H70.9300
N1—C21.354 (2)C8—C91.373 (3)
N1—N21.3893 (19)C8—H80.9300
N1—C31.477 (2)C9—C101.362 (3)
N2—C51.285 (2)C10—C111.381 (3)
C1—C21.490 (3)C10—H100.9300
C1—H1A0.9600C11—H110.9300
C1—H1B0.9600C12—C171.384 (3)
C1—H1C0.9600C12—C131.391 (3)
C3—C61.510 (2)C13—C141.377 (3)
C3—C41.533 (3)C13—H130.9300
C3—H30.9800C14—C151.371 (3)
C4—C51.502 (2)C14—H140.9300
C4—H4A0.9700C15—C161.362 (3)
C4—H4B0.9700C16—C171.380 (3)
C5—C121.465 (2)C16—H160.9300
C6—C111.385 (2)C17—H170.9300
C2—N1—N2122.87 (14)C8—C7—H7119.5
C2—N1—C3124.48 (15)C6—C7—H7119.5
N2—N1—C3112.62 (14)C9—C8—C7118.28 (18)
C5—N2—N1107.76 (14)C9—C8—H8120.9
C2—C1—H1A109.5C7—C8—H8120.9
C2—C1—H1B109.5F1—C9—C10118.61 (18)
H1A—C1—H1B109.5F1—C9—C8118.66 (19)
C2—C1—H1C109.5C10—C9—C8122.73 (18)
H1A—C1—H1C109.5C9—C10—C11118.23 (17)
H1B—C1—H1C109.5C9—C10—H10120.9
O1—C2—N1119.36 (17)C11—C10—H10120.9
O1—C2—C1123.17 (18)C10—C11—C6121.12 (17)
N1—C2—C1117.46 (17)C10—C11—H11119.4
N1—C3—C6112.45 (15)C6—C11—H11119.4
N1—C3—C4100.64 (13)C17—C12—C13118.28 (18)
C6—C3—C4112.75 (14)C17—C12—C5120.02 (17)
N1—C3—H3110.2C13—C12—C5121.70 (17)
C6—C3—H3110.2C14—C13—C12120.43 (19)
C4—C3—H3110.2C14—C13—H13119.8
C5—C4—C3102.19 (14)C12—C13—H13119.8
C5—C4—H4A111.3C15—C14—C13119.92 (19)
C3—C4—H4A111.3C15—C14—H14120.0
C5—C4—H4B111.3C13—C14—H14120.0
C3—C4—H4B111.3C16—C15—C14120.72 (19)
H4A—C4—H4B109.2C16—C15—Cl1119.42 (17)
N2—C5—C12121.50 (16)C14—C15—Cl1119.84 (17)
N2—C5—C4113.79 (16)C15—C16—C17119.62 (19)
C12—C5—C4124.69 (16)C15—C16—H16120.2
C11—C6—C7118.63 (17)C17—C16—H16120.2
C11—C6—C3119.71 (16)C16—C17—C12120.97 (19)
C7—C6—C3121.53 (15)C16—C17—H17119.5
C8—C7—C6120.99 (17)C12—C17—H17119.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4B···O1i0.972.573.425 (2)147

Symmetry codes: (i) −x+2, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2570).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dhal, P. N., Acharya, T. E. & Nayak, A. (1975). J. Indian Chem. Soc.52, 1196–1200.
  • Fahrni, C. J., Yang, L. C. & VanDerveer, D. G. (2003). J. Am. Chem. Soc.125, 3799–3812. [PubMed]
  • Kimura, T., Kai, Y., Yasuoka, N. & Kasai, N. (1977). Acta Cryst. B33, 1786–1792.
  • Lombardino, G. & Ottemes, I. G. (1981). J. Med. Chem.24, 830–834. [PubMed]
  • 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, 3629–3635. [PubMed]
  • Rawal, A. A., Thakor, V. M. & Shah, N. M. (1963). J. Indian Chem. Soc.40, 323–326.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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