Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702781X/lh2418sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680702781X/lh2418Isup2.hkl |
CCDC reference: 654913
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.098
- Data-to-parameter ratio = 13.7
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1-(2,5-dichlorophenyl)-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 stirred in refluxing for 6 h, then the mixture was poured into ice–water to afford a colourless solid. The solid was filtered and washed with water until the pH of solution reached ca 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, C—H distances 0.93–0.96 Å,respectively, and with Uiso = 1.2–1.5Ueq of the parent atoms.
Pyrazoline and its derivatives are useful compounds found to possess antiviral (Rawal et al., 1963), antifungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. 1-Acetyl-3,5-diaryl-2-pyrazoline has been found to inhibit the monoamine oxidases (Manna et al., 2002). As part of our ongoing investgation of pyrazolines and their metal complexes, we report here the crystal strucutre of the title compound.
In the molecule (Fig. 1), all of the bond lengthes and bond angles fall in the normal ranges (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007). The dihedral angles formed by pyrazolinyl ring with phenyl groups at positions 3 and 5 of the pyrazoline are 33.79 (9) and 80.16 (9)°, respectively. Intermolecular C—H···Cl hydrogen bonds form centrosymmetric dimers.
The medicinal and biological properties of pyrazoline derivatives have been reported previously (Rawal et al., 1963; Dhal et al., 1975; Lombardino & Ottemes, 1981; Manna et al., 2002). The bond lengths and angles in the title compound are similar to those in related structures (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007).
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 (Sheldrick, 1990); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure and atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level. |
C17H13Cl2FN2O | F(000) = 1440 |
Mr = 351.19 | Dx = 1.508 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4395 reflections |
a = 21.263 (3) Å | θ = 2.3–27.9° |
b = 9.7330 (15) Å | µ = 0.44 mm−1 |
c = 14.946 (2) Å | T = 298 K |
β = 90.188 (2)° | Prism, colourless |
V = 3093.1 (8) Å3 | 0.50 × 0.44 × 0.10 mm |
Z = 8 |
Bruker SMART CCD area-detector diffractometer | 2874 independent reflections |
Radiation source: fine-focus sealed tube | 2510 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 25.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −25→21 |
Tmin = 0.812, Tmax = 0.958 | k = −10→11 |
7879 measured reflections | l = −18→13 |
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)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0514P)2 + 1.9032P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2874 reflections | Δρmax = 0.24 e Å−3 |
210 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0041 (4) |
C17H13Cl2FN2O | V = 3093.1 (8) Å3 |
Mr = 351.19 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.263 (3) Å | µ = 0.44 mm−1 |
b = 9.7330 (15) Å | T = 298 K |
c = 14.946 (2) Å | 0.50 × 0.44 × 0.10 mm |
β = 90.188 (2)° |
Bruker SMART CCD area-detector diffractometer | 2874 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2510 reflections with I > 2σ(I) |
Tmin = 0.812, Tmax = 0.958 | Rint = 0.020 |
7879 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.24 e Å−3 |
2874 reflections | Δρmin = −0.27 e Å−3 |
210 parameters |
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 | ||
C1 | 0.08006 (9) | 0.13527 (18) | 0.79684 (12) | 0.0476 (4) | |
H1 | 0.0845 | 0.2242 | 0.7750 | 0.057* | |
C2 | 0.08279 (9) | 0.0262 (2) | 0.73842 (13) | 0.0534 (5) | |
H2 | 0.0886 | 0.0403 | 0.6775 | 0.064* | |
C3 | 0.07675 (8) | −0.10387 (18) | 0.77260 (13) | 0.0505 (5) | |
C4 | 0.06837 (8) | −0.12930 (17) | 0.86159 (14) | 0.0497 (4) | |
H4 | 0.0649 | −0.2188 | 0.8828 | 0.060* | |
C5 | 0.06521 (8) | −0.01852 (16) | 0.91935 (12) | 0.0412 (4) | |
H5 | 0.0592 | −0.0336 | 0.9802 | 0.049* | |
C6 | 0.07087 (7) | 0.11499 (16) | 0.88765 (11) | 0.0374 (4) | |
C7 | 0.06956 (8) | 0.23354 (16) | 0.95263 (11) | 0.0399 (4) | |
H7 | 0.0489 | 0.2051 | 1.0081 | 0.048* | |
C8 | 0.13482 (8) | 0.29360 (17) | 0.97412 (13) | 0.0460 (4) | |
H8A | 0.1414 | 0.3009 | 1.0382 | 0.055* | |
H8B | 0.1680 | 0.2378 | 0.9485 | 0.055* | |
C9 | 0.13231 (7) | 0.43332 (16) | 0.93100 (10) | 0.0360 (3) | |
C10 | 0.18616 (7) | 0.52742 (16) | 0.91690 (11) | 0.0389 (4) | |
C11 | 0.23777 (8) | 0.53748 (17) | 0.97440 (13) | 0.0461 (4) | |
C12 | 0.28884 (8) | 0.6198 (2) | 0.95410 (16) | 0.0577 (5) | |
H12 | 0.3232 | 0.6228 | 0.9927 | 0.069* | |
C13 | 0.28910 (9) | 0.6967 (2) | 0.87754 (16) | 0.0595 (6) | |
H13 | 0.3237 | 0.7510 | 0.8634 | 0.071* | |
C14 | 0.23750 (9) | 0.69286 (18) | 0.82176 (13) | 0.0510 (5) | |
C15 | 0.18688 (8) | 0.60848 (17) | 0.83969 (12) | 0.0434 (4) | |
H15 | 0.1530 | 0.6055 | 0.8001 | 0.052* | |
C16 | −0.02538 (7) | 0.36318 (16) | 0.90137 (10) | 0.0375 (4) | |
C17 | −0.05060 (8) | 0.49241 (19) | 0.86017 (13) | 0.0474 (4) | |
H17A | −0.0432 | 0.4910 | 0.7968 | 0.071* | |
H17B | −0.0298 | 0.5704 | 0.8862 | 0.071* | |
H17C | −0.0950 | 0.4986 | 0.8711 | 0.071* | |
Cl1 | 0.23910 (2) | 0.45553 (6) | 1.07729 (4) | 0.06206 (19) | |
Cl2 | 0.23626 (3) | 0.79727 (6) | 0.72775 (4) | 0.0752 (2) | |
F1 | 0.07820 (6) | −0.21172 (12) | 0.71487 (10) | 0.0747 (4) | |
N1 | 0.07803 (6) | 0.46514 (13) | 0.89974 (9) | 0.0367 (3) | |
N2 | 0.03744 (6) | 0.35574 (13) | 0.91536 (10) | 0.0393 (3) | |
O1 | −0.05868 (6) | 0.26601 (13) | 0.92112 (9) | 0.0510 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0561 (10) | 0.0350 (9) | 0.0518 (10) | −0.0013 (8) | 0.0062 (8) | 0.0052 (7) |
C2 | 0.0576 (11) | 0.0549 (11) | 0.0478 (10) | 0.0016 (9) | 0.0035 (8) | −0.0039 (8) |
C3 | 0.0443 (10) | 0.0414 (10) | 0.0657 (12) | 0.0023 (8) | −0.0036 (8) | −0.0146 (8) |
C4 | 0.0450 (10) | 0.0295 (9) | 0.0746 (13) | 0.0000 (7) | −0.0008 (9) | 0.0025 (8) |
C5 | 0.0375 (8) | 0.0347 (8) | 0.0515 (10) | 0.0012 (7) | 0.0007 (7) | 0.0072 (7) |
C6 | 0.0333 (8) | 0.0310 (8) | 0.0478 (9) | −0.0008 (6) | 0.0013 (6) | 0.0031 (7) |
C7 | 0.0405 (9) | 0.0319 (8) | 0.0474 (9) | 0.0023 (6) | 0.0007 (7) | 0.0047 (7) |
C8 | 0.0439 (9) | 0.0354 (9) | 0.0586 (11) | 0.0036 (7) | −0.0072 (8) | −0.0003 (7) |
C9 | 0.0355 (8) | 0.0323 (8) | 0.0402 (8) | 0.0024 (6) | 0.0015 (6) | −0.0058 (6) |
C10 | 0.0321 (8) | 0.0335 (8) | 0.0512 (10) | 0.0012 (6) | 0.0032 (7) | −0.0102 (7) |
C11 | 0.0374 (9) | 0.0410 (9) | 0.0598 (11) | 0.0066 (7) | −0.0025 (8) | −0.0127 (8) |
C12 | 0.0317 (9) | 0.0556 (12) | 0.0858 (15) | 0.0013 (8) | −0.0046 (9) | −0.0199 (11) |
C13 | 0.0370 (10) | 0.0519 (11) | 0.0898 (16) | −0.0094 (8) | 0.0158 (10) | −0.0195 (11) |
C14 | 0.0496 (10) | 0.0429 (10) | 0.0607 (11) | −0.0063 (8) | 0.0181 (9) | −0.0113 (8) |
C15 | 0.0399 (9) | 0.0391 (9) | 0.0512 (10) | −0.0044 (7) | 0.0058 (7) | −0.0083 (7) |
C16 | 0.0355 (8) | 0.0371 (8) | 0.0399 (8) | 0.0002 (7) | 0.0040 (6) | −0.0053 (7) |
C17 | 0.0386 (9) | 0.0481 (10) | 0.0556 (10) | 0.0063 (7) | 0.0004 (8) | 0.0026 (8) |
Cl1 | 0.0583 (3) | 0.0617 (3) | 0.0661 (3) | 0.0081 (2) | −0.0211 (2) | −0.0039 (2) |
Cl2 | 0.0900 (4) | 0.0650 (4) | 0.0708 (4) | −0.0253 (3) | 0.0261 (3) | 0.0020 (3) |
F1 | 0.0812 (9) | 0.0544 (7) | 0.0886 (9) | 0.0047 (6) | −0.0089 (7) | −0.0312 (6) |
N1 | 0.0344 (7) | 0.0296 (7) | 0.0462 (8) | −0.0017 (5) | 0.0037 (6) | −0.0014 (5) |
N2 | 0.0346 (7) | 0.0280 (7) | 0.0554 (8) | −0.0008 (5) | 0.0008 (6) | 0.0034 (6) |
O1 | 0.0399 (7) | 0.0480 (7) | 0.0652 (8) | −0.0094 (5) | 0.0035 (6) | 0.0038 (6) |
C1—C2 | 1.376 (3) | C9—C10 | 1.482 (2) |
C1—C6 | 1.386 (2) | C10—C11 | 1.395 (2) |
C1—H1 | 0.9300 | C10—C15 | 1.398 (2) |
C2—C3 | 1.371 (3) | C11—C12 | 1.384 (3) |
C2—H2 | 0.9300 | C11—Cl1 | 1.733 (2) |
C3—F1 | 1.359 (2) | C12—C13 | 1.368 (3) |
C3—C4 | 1.365 (3) | C12—H12 | 0.9300 |
C4—C5 | 1.383 (2) | C13—C14 | 1.376 (3) |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—C6 | 1.388 (2) | C14—C15 | 1.381 (2) |
C5—H5 | 0.9300 | C14—Cl2 | 1.734 (2) |
C6—C7 | 1.509 (2) | C15—H15 | 0.9300 |
C7—N2 | 1.479 (2) | C16—O1 | 1.2183 (19) |
C7—C8 | 1.539 (2) | C16—N2 | 1.353 (2) |
C7—H7 | 0.9800 | C16—C17 | 1.499 (2) |
C8—C9 | 1.506 (2) | C17—H17A | 0.9600 |
C8—H8A | 0.9700 | C17—H17B | 0.9600 |
C8—H8B | 0.9700 | C17—H17C | 0.9600 |
C9—N1 | 1.282 (2) | N1—N2 | 1.3909 (18) |
C2—C1—C6 | 121.19 (16) | C10—C9—C8 | 126.35 (14) |
C2—C1—H1 | 119.4 | C11—C10—C15 | 117.26 (15) |
C6—C1—H1 | 119.4 | C11—C10—C9 | 124.22 (16) |
C3—C2—C1 | 118.15 (18) | C15—C10—C9 | 118.48 (15) |
C3—C2—H2 | 120.9 | C12—C11—C10 | 121.45 (18) |
C1—C2—H2 | 120.9 | C12—C11—Cl1 | 116.78 (15) |
F1—C3—C4 | 118.80 (17) | C10—C11—Cl1 | 121.67 (14) |
F1—C3—C2 | 118.30 (18) | C13—C12—C11 | 120.38 (18) |
C4—C3—C2 | 122.89 (17) | C13—C12—H12 | 119.8 |
C3—C4—C5 | 118.26 (16) | C11—C12—H12 | 119.8 |
C3—C4—H4 | 120.9 | C12—C13—C14 | 119.11 (17) |
C5—C4—H4 | 120.9 | C12—C13—H13 | 120.4 |
C4—C5—C6 | 120.81 (17) | C14—C13—H13 | 120.4 |
C4—C5—H5 | 119.6 | C13—C14—C15 | 121.27 (19) |
C6—C5—H5 | 119.6 | C13—C14—Cl2 | 118.99 (15) |
C1—C6—C5 | 118.69 (15) | C15—C14—Cl2 | 119.74 (16) |
C1—C6—C7 | 121.63 (14) | C14—C15—C10 | 120.44 (17) |
C5—C6—C7 | 119.63 (15) | C14—C15—H15 | 119.8 |
N2—C7—C6 | 112.46 (14) | C10—C15—H15 | 119.8 |
N2—C7—C8 | 100.84 (12) | O1—C16—N2 | 119.67 (15) |
C6—C7—C8 | 113.98 (13) | O1—C16—C17 | 122.93 (15) |
N2—C7—H7 | 109.7 | N2—C16—C17 | 117.39 (14) |
C6—C7—H7 | 109.7 | C16—C17—H17A | 109.5 |
C8—C7—H7 | 109.7 | C16—C17—H17B | 109.5 |
C9—C8—C7 | 102.89 (13) | H17A—C17—H17B | 109.5 |
C9—C8—H8A | 111.2 | C16—C17—H17C | 109.5 |
C7—C8—H8A | 111.2 | H17A—C17—H17C | 109.5 |
C9—C8—H8B | 111.2 | H17B—C17—H17C | 109.5 |
C7—C8—H8B | 111.2 | C9—N1—N2 | 108.20 (13) |
H8A—C8—H8B | 109.1 | C16—N2—N1 | 123.08 (13) |
N1—C9—C10 | 119.61 (14) | C16—N2—C7 | 123.74 (13) |
N1—C9—C8 | 113.88 (14) | N1—N2—C7 | 113.12 (12) |
C6—C1—C2—C3 | −0.6 (3) | C15—C10—C11—Cl1 | 173.58 (12) |
C1—C2—C3—F1 | 178.74 (17) | C9—C10—C11—Cl1 | −8.7 (2) |
C1—C2—C3—C4 | −0.2 (3) | C10—C11—C12—C13 | 1.8 (3) |
F1—C3—C4—C5 | −178.22 (15) | Cl1—C11—C12—C13 | −174.68 (15) |
C2—C3—C4—C5 | 0.7 (3) | C11—C12—C13—C14 | 1.0 (3) |
C3—C4—C5—C6 | −0.5 (3) | C12—C13—C14—C15 | −2.8 (3) |
C2—C1—C6—C5 | 0.8 (3) | C12—C13—C14—Cl2 | 176.69 (14) |
C2—C1—C6—C7 | 178.31 (17) | C13—C14—C15—C10 | 1.9 (3) |
C4—C5—C6—C1 | −0.3 (2) | Cl2—C14—C15—C10 | −177.67 (12) |
C4—C5—C6—C7 | −177.83 (15) | C11—C10—C15—C14 | 0.9 (2) |
C1—C6—C7—N2 | 38.3 (2) | C9—C10—C15—C14 | −176.98 (14) |
C5—C6—C7—N2 | −144.20 (15) | C10—C9—N1—N2 | 175.10 (13) |
C1—C6—C7—C8 | −75.7 (2) | C8—C9—N1—N2 | −0.65 (18) |
C5—C6—C7—C8 | 101.81 (17) | O1—C16—N2—N1 | −175.94 (14) |
N2—C7—C8—C9 | −9.30 (16) | C17—C16—N2—N1 | 5.0 (2) |
C6—C7—C8—C9 | 111.43 (15) | O1—C16—N2—C7 | 1.1 (2) |
C7—C8—C9—N1 | 6.82 (19) | C17—C16—N2—C7 | −177.93 (15) |
C7—C8—C9—C10 | −168.60 (15) | C9—N1—N2—C16 | 170.90 (15) |
N1—C9—C10—C11 | 152.10 (15) | C9—N1—N2—C7 | −6.41 (18) |
C8—C9—C10—C11 | −32.7 (2) | C6—C7—N2—C16 | 70.98 (19) |
N1—C9—C10—C15 | −30.2 (2) | C8—C7—N2—C16 | −167.22 (15) |
C8—C9—C10—C15 | 144.99 (16) | C6—C7—N2—N1 | −111.73 (15) |
C15—C10—C11—C12 | −2.7 (2) | C8—C7—N2—N1 | 10.07 (17) |
C9—C10—C11—C12 | 175.05 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···Cl1i | 0.97 | 2.76 | 3.697 (3) | 163 |
Symmetry code: (i) −x+1/2, −y+1/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C17H13Cl2FN2O |
Mr | 351.19 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 21.263 (3), 9.7330 (15), 14.946 (2) |
β (°) | 90.188 (2) |
V (Å3) | 3093.1 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.44 |
Crystal size (mm) | 0.50 × 0.44 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.812, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7879, 2874, 2510 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.098, 1.04 |
No. of reflections | 2874 |
No. of parameters | 210 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.27 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1990), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···Cl1i | 0.970 | 2.76 | 3.697 (3) | 163 |
Symmetry code: (i) −x+1/2, −y+1/2, −z+2. |
Pyrazoline and its derivatives are useful compounds found to possess antiviral (Rawal et al., 1963), antifungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. 1-Acetyl-3,5-diaryl-2-pyrazoline has been found to inhibit the monoamine oxidases (Manna et al., 2002). As part of our ongoing investgation of pyrazolines and their metal complexes, we report here the crystal strucutre of the title compound.
In the molecule (Fig. 1), all of the bond lengthes and bond angles fall in the normal ranges (Fahrni et al., 2003; Kimura et al., 1977; Guo et al., 2007). The dihedral angles formed by pyrazolinyl ring with phenyl groups at positions 3 and 5 of the pyrazoline are 33.79 (9) and 80.16 (9)°, respectively. Intermolecular C—H···Cl hydrogen bonds form centrosymmetric dimers.