Acta Cryst. (2008). E64, o1391 [ doi:10.1107/S1600536808018333 ]
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.
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.
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.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./at2570fig1thm.gif)
| Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level. |
![[Figure 2]](./at2570fig2thm.gif)
| Fig. 2. View of the crysytal packing of (I) in the unit cell. |
| C17H14ClFN2O | F000 = 656 |
| Mr = 316.75 | Dx = 1.389 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 2887 reflections |
| a = 14.5425 (19) Å | θ = 2.9–25.9º |
| b = 11.3580 (14) Å | µ = 0.27 mm−1 |
| c = 9.6494 (13) Å | T = 273 (2) K |
| β = 108.154 (2)º | Bar, colourless |
| V = 1514.5 (3) Å3 | 0.14 × 0.12 × 0.06 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 2077 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.021 |
| Monochromator: graphite | θmax = 25.1º |
| T = 273(2) K | θmin = 2.3º |
| φ and ω scans | h = −17→17 |
| Absorption correction: none | k = −13→11 |
| 7793 measured reflections | l = −11→9 |
| 2676 independent reflections |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-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 = 1.03 | Δρmax = 0.20 e Å−3 |
| 2676 reflections | Δρmin = −0.21 e Å−3 |
| 200 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0031 (10) |
| Secondary atom site location: difference Fourier map |
| C17H14ClFN2O | V = 1514.5 (3) Å3 |
| Mr = 316.75 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 14.5425 (19) Å | µ = 0.27 mm−1 |
| b = 11.3580 (14) Å | T = 273 (2) K |
| c = 9.6494 (13) Å | 0.14 × 0.12 × 0.06 mm |
| β = 108.154 (2)º |
| Bruker SMART CCD area-detector diffractometer | 2676 independent reflections |
| Absorption correction: none | 2077 reflections with I > 2σ(I) |
| 7793 measured reflections | Rint = 0.021 |
| R[F2 > 2σ(F2)] = 0.037 | 200 parameters |
| wR(F2) = 0.098 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 0.20 e Å−3 |
| 2676 reflections | Δρmin = −0.21 e Å−3 |
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. |
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.45884 (5) | 0.34606 (6) | 0.02764 (8) | 0.0949 (3) | |
| F1 | 0.70769 (11) | −0.14714 (11) | 1.10898 (14) | 0.0851 (4) | |
| O1 | 1.00066 (10) | −0.13914 (13) | 0.72130 (15) | 0.0685 (4) | |
| N1 | 0.88095 (10) | −0.02205 (13) | 0.59652 (15) | 0.0491 (4) | |
| N2 | 0.80952 (10) | 0.00960 (13) | 0.46876 (15) | 0.0477 (4) | |
| C1 | 0.93307 (15) | −0.17908 (18) | 0.4668 (2) | 0.0610 (5) | |
| H1A | 0.9661 | −0.1361 | 0.4109 | 0.092* | |
| H1B | 0.8660 | −0.1873 | 0.4111 | 0.092* | |
| H1C | 0.9617 | −0.2557 | 0.4898 | 0.092* | |
| C2 | 0.94144 (13) | −0.11419 (16) | 0.6044 (2) | 0.0494 (4) | |
| C3 | 0.88134 (13) | 0.05353 (16) | 0.72122 (18) | 0.0477 (4) | |
| H3 | 0.9474 | 0.0797 | 0.7730 | 0.057* | |
| C4 | 0.82018 (14) | 0.15743 (16) | 0.64155 (19) | 0.0500 (5) | |
| H4A | 0.7728 | 0.1808 | 0.6881 | 0.060* | |
| H4B | 0.8604 | 0.2246 | 0.6373 | 0.060* | |
| C5 | 0.77233 (12) | 0.10719 (16) | 0.49247 (18) | 0.0454 (4) | |
| C6 | 0.83785 (12) | −0.00700 (15) | 0.82540 (18) | 0.0446 (4) | |
| C7 | 0.76197 (13) | −0.08590 (17) | 0.7766 (2) | 0.0530 (5) | |
| H7 | 0.7404 | −0.1070 | 0.6786 | 0.064* | |
| C8 | 0.71794 (15) | −0.13366 (18) | 0.8711 (2) | 0.0593 (5) | |
| H8 | 0.6671 | −0.1868 | 0.8382 | 0.071* | |
| C9 | 0.75105 (15) | −0.10081 (18) | 1.0151 (2) | 0.0574 (5) | |
| C10 | 0.82613 (14) | −0.02457 (17) | 1.0681 (2) | 0.0537 (5) | |
| H10 | 0.8474 | −0.0044 | 1.1664 | 0.064* | |
| C11 | 0.86977 (13) | 0.02200 (16) | 0.97206 (18) | 0.0481 (4) | |
| H11 | 0.9215 | 0.0737 | 1.0065 | 0.058* | |
| C12 | 0.69236 (12) | 0.16303 (16) | 0.37998 (19) | 0.0455 (4) | |
| C13 | 0.63734 (14) | 0.10150 (18) | 0.2576 (2) | 0.0557 (5) | |
| H13 | 0.6499 | 0.0222 | 0.2473 | 0.067* | |
| C14 | 0.56443 (15) | 0.15720 (19) | 0.1515 (2) | 0.0621 (5) | |
| H14 | 0.5275 | 0.1154 | 0.0703 | 0.075* | |
| C15 | 0.54634 (13) | 0.27427 (18) | 0.1657 (2) | 0.0588 (5) | |
| C16 | 0.59780 (14) | 0.33572 (18) | 0.2860 (3) | 0.0630 (6) | |
| H16 | 0.5842 | 0.4147 | 0.2957 | 0.076* | |
| C17 | 0.67020 (14) | 0.28007 (17) | 0.3936 (2) | 0.0558 (5) | |
| H17 | 0.7046 | 0.3218 | 0.4764 | 0.067* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0695 (4) | 0.0900 (5) | 0.1055 (5) | 0.0056 (3) | −0.0012 (3) | 0.0364 (4) |
| F1 | 0.1184 (11) | 0.0792 (9) | 0.0750 (9) | −0.0204 (8) | 0.0552 (8) | 0.0010 (7) |
| O1 | 0.0622 (9) | 0.0758 (10) | 0.0578 (9) | 0.0125 (7) | 0.0045 (7) | 0.0014 (7) |
| N1 | 0.0505 (8) | 0.0581 (9) | 0.0370 (8) | 0.0056 (7) | 0.0111 (7) | −0.0052 (7) |
| N2 | 0.0485 (8) | 0.0565 (9) | 0.0372 (8) | 0.0015 (7) | 0.0121 (6) | −0.0026 (7) |
| C1 | 0.0680 (13) | 0.0577 (12) | 0.0615 (12) | 0.0051 (10) | 0.0261 (10) | −0.0078 (10) |
| C2 | 0.0464 (10) | 0.0528 (11) | 0.0501 (11) | −0.0025 (9) | 0.0167 (9) | 0.0005 (9) |
| C3 | 0.0456 (10) | 0.0571 (11) | 0.0393 (9) | −0.0055 (8) | 0.0115 (8) | −0.0086 (8) |
| C4 | 0.0573 (11) | 0.0502 (11) | 0.0437 (10) | −0.0045 (9) | 0.0177 (8) | −0.0045 (8) |
| C5 | 0.0474 (10) | 0.0504 (11) | 0.0413 (9) | −0.0051 (8) | 0.0180 (8) | −0.0026 (8) |
| C6 | 0.0431 (9) | 0.0497 (10) | 0.0381 (9) | 0.0034 (8) | 0.0084 (7) | −0.0024 (8) |
| C7 | 0.0529 (11) | 0.0613 (12) | 0.0416 (10) | −0.0062 (9) | 0.0098 (8) | −0.0067 (9) |
| C8 | 0.0599 (12) | 0.0570 (12) | 0.0623 (13) | −0.0115 (10) | 0.0209 (10) | −0.0044 (10) |
| C9 | 0.0710 (13) | 0.0546 (12) | 0.0542 (12) | 0.0017 (10) | 0.0302 (10) | 0.0049 (9) |
| C10 | 0.0666 (12) | 0.0541 (11) | 0.0388 (10) | 0.0037 (10) | 0.0142 (9) | −0.0018 (8) |
| C11 | 0.0487 (10) | 0.0498 (10) | 0.0416 (10) | 0.0001 (8) | 0.0078 (8) | −0.0043 (8) |
| C12 | 0.0452 (10) | 0.0504 (11) | 0.0441 (10) | −0.0035 (8) | 0.0188 (8) | 0.0003 (8) |
| C13 | 0.0609 (12) | 0.0519 (11) | 0.0513 (11) | −0.0008 (9) | 0.0131 (9) | −0.0012 (9) |
| C14 | 0.0592 (12) | 0.0677 (14) | 0.0526 (12) | −0.0076 (10) | 0.0075 (10) | 0.0003 (10) |
| C15 | 0.0450 (11) | 0.0608 (13) | 0.0685 (13) | −0.0036 (9) | 0.0144 (9) | 0.0141 (10) |
| C16 | 0.0534 (12) | 0.0488 (11) | 0.0880 (16) | 0.0000 (9) | 0.0238 (11) | 0.0063 (11) |
| C17 | 0.0511 (11) | 0.0532 (12) | 0.0636 (12) | −0.0058 (9) | 0.0183 (10) | −0.0062 (10) |
| Cl1—C15 | 1.733 (2) | C6—C7 | 1.385 (2) |
| F1—C9 | 1.361 (2) | C7—C8 | 1.378 (3) |
| O1—C2 | 1.220 (2) | C7—H7 | 0.9300 |
| N1—C2 | 1.354 (2) | C8—C9 | 1.373 (3) |
| N1—N2 | 1.3893 (19) | C8—H8 | 0.9300 |
| N1—C3 | 1.477 (2) | C9—C10 | 1.362 (3) |
| N2—C5 | 1.285 (2) | C10—C11 | 1.381 (3) |
| C1—C2 | 1.490 (3) | C10—H10 | 0.9300 |
| C1—H1A | 0.9600 | C11—H11 | 0.9300 |
| C1—H1B | 0.9600 | C12—C17 | 1.384 (3) |
| C1—H1C | 0.9600 | C12—C13 | 1.391 (3) |
| C3—C6 | 1.510 (2) | C13—C14 | 1.377 (3) |
| C3—C4 | 1.533 (3) | C13—H13 | 0.9300 |
| C3—H3 | 0.9800 | C14—C15 | 1.371 (3) |
| C4—C5 | 1.502 (2) | C14—H14 | 0.9300 |
| C4—H4A | 0.9700 | C15—C16 | 1.362 (3) |
| C4—H4B | 0.9700 | C16—C17 | 1.380 (3) |
| C5—C12 | 1.465 (2) | C16—H16 | 0.9300 |
| C6—C11 | 1.385 (2) | C17—H17 | 0.9300 |
| C2—N1—N2 | 122.87 (14) | C8—C7—H7 | 119.5 |
| C2—N1—C3 | 124.48 (15) | C6—C7—H7 | 119.5 |
| N2—N1—C3 | 112.62 (14) | C9—C8—C7 | 118.28 (18) |
| C5—N2—N1 | 107.76 (14) | C9—C8—H8 | 120.9 |
| C2—C1—H1A | 109.5 | C7—C8—H8 | 120.9 |
| C2—C1—H1B | 109.5 | F1—C9—C10 | 118.61 (18) |
| H1A—C1—H1B | 109.5 | F1—C9—C8 | 118.66 (19) |
| C2—C1—H1C | 109.5 | C10—C9—C8 | 122.73 (18) |
| H1A—C1—H1C | 109.5 | C9—C10—C11 | 118.23 (17) |
| H1B—C1—H1C | 109.5 | C9—C10—H10 | 120.9 |
| O1—C2—N1 | 119.36 (17) | C11—C10—H10 | 120.9 |
| O1—C2—C1 | 123.17 (18) | C10—C11—C6 | 121.12 (17) |
| N1—C2—C1 | 117.46 (17) | C10—C11—H11 | 119.4 |
| N1—C3—C6 | 112.45 (15) | C6—C11—H11 | 119.4 |
| N1—C3—C4 | 100.64 (13) | C17—C12—C13 | 118.28 (18) |
| C6—C3—C4 | 112.75 (14) | C17—C12—C5 | 120.02 (17) |
| N1—C3—H3 | 110.2 | C13—C12—C5 | 121.70 (17) |
| C6—C3—H3 | 110.2 | C14—C13—C12 | 120.43 (19) |
| C4—C3—H3 | 110.2 | C14—C13—H13 | 119.8 |
| C5—C4—C3 | 102.19 (14) | C12—C13—H13 | 119.8 |
| C5—C4—H4A | 111.3 | C15—C14—C13 | 119.92 (19) |
| C3—C4—H4A | 111.3 | C15—C14—H14 | 120.0 |
| C5—C4—H4B | 111.3 | C13—C14—H14 | 120.0 |
| C3—C4—H4B | 111.3 | C16—C15—C14 | 120.72 (19) |
| H4A—C4—H4B | 109.2 | C16—C15—Cl1 | 119.42 (17) |
| N2—C5—C12 | 121.50 (16) | C14—C15—Cl1 | 119.84 (17) |
| N2—C5—C4 | 113.79 (16) | C15—C16—C17 | 119.62 (19) |
| C12—C5—C4 | 124.69 (16) | C15—C16—H16 | 120.2 |
| C11—C6—C7 | 118.63 (17) | C17—C16—H16 | 120.2 |
| C11—C6—C3 | 119.71 (16) | C16—C17—C12 | 120.97 (19) |
| C7—C6—C3 | 121.53 (15) | C16—C17—H17 | 119.5 |
| C8—C7—C6 | 120.99 (17) | C12—C17—H17 | 119.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4B···O1i | 0.97 | 2.57 | 3.425 (2) | 147 |
| Symmetry codes: (i) −x+2, y+1/2, −z+3/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C4—H4B···O1i | 0.97 | 2.57 | 3.425 (2) | 147 |
| Symmetry codes: (i) −x+2, y+1/2, −z+3/2. |
The authors thank the Sparking Plan of Shandong Province (grant No. 200674006017) and the National Sparking Plan Project (grant No. 2007E740083).
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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.