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The title compound, C19H15ClN2O, was prepared from phenyl­hydrazine and 1-(4-chloro­phen­yl)-3-(2-fur­yl)-2-propen­yl-1-ketone. The pyrazoline ring forms a dihedral angle of 11.09 (10)° with the phenyl ring, 89.23 (1)° with the furan ring and 7.58 (10)° with the chloro­phenyl ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027080/at2318sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027080/at2318Isup2.hkl
Contains datablock I

CCDC reference: 654908

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.126
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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

As important and useful five-membered heterocyclic compounds, pyrazoline and its derivatives were found to possess antiviral (Rawal et al., 1963), antifungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. Several 1,3,5-triaryl-2-pyrazolines were also used as scintillation solutes (Wiley et al.,1958). We report herein the crystal structure of the title compound (I).

In the structure of (I) (Fig. 1), all of the bond lengths and bond angles fall in the normal range (Rurack, et al., 2000; Fahrni et al., 2003; Guo et al., 2006). The mean plane of pyrazolinyl ring N1/N2/C7/C12/C13 makes dihedral angles of 11.09 (10), 7.58 (10) and 89.23 (1)°, with phenyl ring C1—C6 and benzene ring C14—C19 and furan ring O1/C8—C11, respectively.

Related literature top

For related literature, see: Dhal et al. (1975); Fahrni et al. (2003); Guo et al. (2006); Lombardino & Ottemes (1981); Orzeszka et al. (2000); Rawal et al. (1963); Rurack et al. (2000); Wiley et al. (1958).

Experimental top

1-(p-Chloromophenyl)-3-(p-fluorophenyl)-2-propenyl-1-ketone (0.02 mol) and phenylhydrazine (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 yellow solids·The solids were filtrated and washed with water until the pH of solution is about to 7.0. Finally, the red 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 top

H atoms were fixed geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å and with Uiso(H) = 1.2Ueq(C).

Structure description top

As important and useful five-membered heterocyclic compounds, pyrazoline and its derivatives were found to possess antiviral (Rawal et al., 1963), antifungal (Dhal et al., 1975), and immunosuppressive (Lombardino & Ottemes, 1981) activities. Several 1,3,5-triaryl-2-pyrazolines were also used as scintillation solutes (Wiley et al.,1958). We report herein the crystal structure of the title compound (I).

In the structure of (I) (Fig. 1), all of the bond lengths and bond angles fall in the normal range (Rurack, et al., 2000; Fahrni et al., 2003; Guo et al., 2006). The mean plane of pyrazolinyl ring N1/N2/C7/C12/C13 makes dihedral angles of 11.09 (10), 7.58 (10) and 89.23 (1)°, with phenyl ring C1—C6 and benzene ring C14—C19 and furan ring O1/C8—C11, respectively.

For related literature, see: Dhal et al. (1975); Fahrni et al. (2003); Guo et al. (2006); Lombardino & Ottemes (1981); Orzeszka et al. (2000); Rawal et al. (1963); Rurack et al. (2000); Wiley et al. (1958).

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.
3-(4-Chlorophenyl)-5-(2-furyl)-1-phenyl-2-pyrazoline top
Crystal data top
C19H15ClN2OZ = 2
Mr = 322.78F(000) = 336
Triclinic, P1Dx = 1.357 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.9247 (14) ÅCell parameters from 2279 reflections
b = 8.482 (2) Åθ = 2.5–27.7°
c = 16.284 (4) ŵ = 0.25 mm1
α = 101.424 (3)°T = 298 K
β = 90.909 (3)°Bar, colourless
γ = 99.468 (3)°0.50 × 0.27 × 0.24 mm
V = 790.2 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2425 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 25.5°, θmin = 2.5°
φ and ω scansh = 67
4160 measured reflectionsk = 910
2886 independent reflectionsl = 1910
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0609P)2 + 0.1935P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2886 reflectionsΔρmax = 0.19 e Å3
209 parametersΔρmin = 0.35 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.050 (6)
Crystal data top
C19H15ClN2Oγ = 99.468 (3)°
Mr = 322.78V = 790.2 (3) Å3
Triclinic, P1Z = 2
a = 5.9247 (14) ÅMo Kα radiation
b = 8.482 (2) ŵ = 0.25 mm1
c = 16.284 (4) ÅT = 298 K
α = 101.424 (3)°0.50 × 0.27 × 0.24 mm
β = 90.909 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2425 reflections with I > 2σ(I)
4160 measured reflectionsRint = 0.019
2886 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.05Δρmax = 0.19 e Å3
2886 reflectionsΔρmin = 0.35 e Å3
209 parameters
Special details top

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) top
xyzUiso*/Ueq
C10.2263 (3)0.3482 (2)0.90901 (11)0.0489 (4)
H10.33160.42970.94270.059*
C20.0290 (4)0.2820 (2)0.94263 (13)0.0580 (5)
H20.00290.31900.99880.070*
C30.1287 (4)0.1619 (3)0.89393 (14)0.0641 (6)
H30.26120.11720.91670.077*
C40.0881 (3)0.1084 (2)0.81056 (13)0.0574 (5)
H40.19510.02760.77730.069*
C50.1076 (3)0.1722 (2)0.77587 (11)0.0458 (4)
H50.13250.13410.71970.055*
C60.2692 (3)0.29446 (19)0.82523 (10)0.0403 (4)
C70.6222 (3)0.5127 (2)0.83136 (11)0.0431 (4)
H70.68030.50250.88640.052*
C80.5065 (3)0.6574 (2)0.84082 (11)0.0436 (4)
C90.4495 (4)0.7644 (2)0.90572 (13)0.0587 (5)
H90.47990.76680.96220.070*
C100.3343 (4)0.8731 (2)0.87274 (16)0.0645 (6)
H100.27420.96020.90310.077*
C110.3291 (4)0.8265 (3)0.79033 (16)0.0649 (6)
H110.26330.87730.75270.078*
C120.8169 (3)0.5140 (2)0.77046 (11)0.0475 (4)
H12A0.84970.61740.75240.057*
H12B0.95550.49300.79570.057*
C130.7202 (3)0.3770 (2)0.69861 (11)0.0430 (4)
C140.8373 (3)0.3343 (2)0.62124 (11)0.0448 (4)
C150.7365 (4)0.2127 (3)0.55436 (13)0.0589 (5)
H150.58820.15870.55800.071*
C160.8527 (4)0.1711 (3)0.48325 (13)0.0668 (6)
H160.78380.08940.43900.080*
C171.0720 (4)0.2513 (3)0.47784 (12)0.0567 (5)
C181.1761 (4)0.3720 (3)0.54203 (13)0.0597 (5)
H181.32420.42560.53770.072*
C191.0582 (3)0.4134 (3)0.61333 (12)0.0542 (5)
H191.12810.49580.65700.065*
Cl11.21959 (12)0.20021 (9)0.38763 (4)0.0841 (3)
N10.5275 (2)0.29548 (17)0.71306 (9)0.0448 (4)
N20.4665 (3)0.36129 (17)0.79203 (9)0.0483 (4)
O10.4334 (2)0.69357 (17)0.76793 (8)0.0591 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0487 (11)0.0472 (10)0.0446 (10)0.0019 (8)0.0019 (8)0.0034 (7)
C20.0607 (12)0.0584 (11)0.0483 (11)0.0001 (9)0.0108 (9)0.0025 (9)
C30.0523 (12)0.0603 (12)0.0695 (13)0.0068 (9)0.0150 (10)0.0015 (10)
C40.0471 (11)0.0499 (10)0.0644 (12)0.0053 (8)0.0007 (9)0.0028 (9)
C50.0475 (10)0.0405 (9)0.0463 (9)0.0073 (7)0.0009 (7)0.0015 (7)
C60.0406 (9)0.0358 (8)0.0450 (9)0.0072 (7)0.0002 (7)0.0087 (7)
C70.0410 (9)0.0421 (9)0.0416 (9)0.0009 (7)0.0040 (7)0.0031 (7)
C80.0376 (9)0.0432 (9)0.0449 (9)0.0022 (7)0.0002 (7)0.0050 (7)
C90.0664 (13)0.0514 (11)0.0528 (11)0.0085 (9)0.0049 (9)0.0016 (9)
C100.0569 (13)0.0439 (10)0.0876 (16)0.0103 (9)0.0074 (11)0.0006 (10)
C110.0594 (13)0.0516 (11)0.0845 (16)0.0141 (10)0.0090 (11)0.0135 (11)
C120.0397 (10)0.0479 (10)0.0514 (10)0.0059 (7)0.0004 (7)0.0033 (8)
C130.0403 (10)0.0449 (9)0.0433 (9)0.0084 (7)0.0022 (7)0.0075 (7)
C140.0428 (10)0.0480 (9)0.0439 (9)0.0094 (7)0.0006 (7)0.0087 (7)
C150.0549 (12)0.0607 (12)0.0527 (11)0.0011 (9)0.0036 (9)0.0006 (9)
C160.0686 (14)0.0691 (13)0.0532 (12)0.0028 (11)0.0055 (10)0.0029 (10)
C170.0634 (13)0.0652 (12)0.0452 (10)0.0201 (10)0.0083 (9)0.0119 (9)
C180.0464 (11)0.0729 (13)0.0593 (12)0.0070 (9)0.0086 (9)0.0144 (10)
C190.0473 (11)0.0626 (11)0.0479 (10)0.0052 (9)0.0006 (8)0.0032 (9)
Cl10.0923 (5)0.1062 (5)0.0554 (4)0.0281 (4)0.0260 (3)0.0092 (3)
N10.0462 (9)0.0446 (8)0.0409 (8)0.0060 (7)0.0013 (6)0.0036 (6)
N20.0503 (9)0.0426 (8)0.0441 (8)0.0021 (6)0.0059 (6)0.0024 (6)
O10.0660 (9)0.0584 (8)0.0532 (8)0.0172 (7)0.0056 (6)0.0072 (6)
Geometric parameters (Å, º) top
C1—C21.381 (3)C10—H100.9300
C1—C61.392 (2)C11—O11.364 (2)
C1—H10.9300C11—H110.9300
C2—C31.372 (3)C12—C131.506 (2)
C2—H20.9300C12—H12A0.9700
C3—C41.382 (3)C12—H12B0.9700
C3—H30.9300C13—N11.285 (2)
C4—C51.375 (3)C13—C141.459 (2)
C4—H40.9300C14—C191.389 (3)
C5—C61.399 (2)C14—C151.393 (3)
C5—H50.9300C15—C161.372 (3)
C6—N21.380 (2)C15—H150.9300
C7—N21.475 (2)C16—C171.377 (3)
C7—C81.485 (2)C16—H160.9300
C7—C121.533 (2)C17—C181.367 (3)
C7—H70.9800C17—Cl11.739 (2)
C8—C91.337 (3)C18—C191.380 (3)
C8—O11.365 (2)C18—H180.9300
C9—C101.412 (3)C19—H190.9300
C9—H90.9300N1—N21.376 (2)
C10—C111.320 (3)
C2—C1—C6120.70 (17)C10—C11—H11124.7
C2—C1—H1119.6O1—C11—H11124.7
C6—C1—H1119.6C13—C12—C7102.38 (14)
C3—C2—C1120.57 (19)C13—C12—H12A111.3
C3—C2—H2119.7C7—C12—H12A111.3
C1—C2—H2119.7C13—C12—H12B111.3
C2—C3—C4119.11 (18)C7—C12—H12B111.3
C2—C3—H3120.4H12A—C12—H12B109.2
C4—C3—H3120.4N1—C13—C14122.54 (16)
C5—C4—C3121.30 (18)N1—C13—C12113.56 (15)
C5—C4—H4119.3C14—C13—C12123.84 (16)
C3—C4—H4119.3C19—C14—C15117.91 (17)
C4—C5—C6119.85 (17)C19—C14—C13120.04 (16)
C4—C5—H5120.1C15—C14—C13122.04 (17)
C6—C5—H5120.1C16—C15—C14121.01 (19)
N2—C6—C1120.40 (15)C16—C15—H15119.5
N2—C6—C5121.13 (16)C14—C15—H15119.5
C1—C6—C5118.47 (16)C15—C16—C17119.5 (2)
N2—C7—C8111.74 (14)C15—C16—H16120.3
N2—C7—C12101.52 (13)C17—C16—H16120.3
C8—C7—C12114.22 (14)C18—C17—C16121.16 (19)
N2—C7—H7109.7C18—C17—Cl1119.11 (17)
C8—C7—H7109.7C16—C17—Cl1119.72 (16)
C12—C7—H7109.7C17—C18—C19119.06 (19)
C9—C8—O1109.14 (17)C17—C18—H18120.5
C9—C8—C7135.12 (17)C19—C18—H18120.5
O1—C8—C7115.72 (15)C18—C19—C14121.38 (18)
C8—C9—C10107.40 (19)C18—C19—H19119.3
C8—C9—H9126.3C14—C19—H19119.3
C10—C9—H9126.3C13—N1—N2108.75 (14)
C11—C10—C9106.41 (19)N1—N2—C6121.33 (14)
C11—C10—H10126.8N1—N2—C7112.76 (13)
C9—C10—H10126.8C6—N2—C7125.74 (14)
C10—C11—O1110.64 (19)C11—O1—C8106.40 (16)
C6—C1—C2—C30.1 (3)C13—C14—C15—C16177.95 (19)
C1—C2—C3—C40.2 (3)C14—C15—C16—C170.2 (3)
C2—C3—C4—C50.5 (3)C15—C16—C17—C180.2 (3)
C3—C4—C5—C60.4 (3)C15—C16—C17—Cl1179.60 (17)
C2—C1—C6—N2179.94 (17)C16—C17—C18—C190.1 (3)
C2—C1—C6—C50.2 (3)Cl1—C17—C18—C19179.52 (16)
C4—C5—C6—N2179.69 (16)C17—C18—C19—C140.4 (3)
C4—C5—C6—C10.1 (3)C15—C14—C19—C180.7 (3)
N2—C7—C8—C9115.2 (2)C13—C14—C19—C18177.90 (17)
C12—C7—C8—C9130.3 (2)C14—C13—N1—N2177.55 (15)
N2—C7—C8—O163.19 (19)C12—C13—N1—N20.4 (2)
C12—C7—C8—O151.3 (2)C13—N1—N2—C6178.02 (15)
O1—C8—C9—C100.2 (2)C13—N1—N2—C76.48 (19)
C7—C8—C9—C10178.27 (19)C1—C6—N2—N1171.10 (15)
C8—C9—C10—C110.2 (2)C5—C6—N2—N19.1 (2)
C9—C10—C11—O10.2 (3)C1—C6—N2—C714.0 (3)
N2—C7—C12—C139.09 (16)C5—C6—N2—C7165.74 (16)
C8—C7—C12—C13111.32 (16)C8—C7—N2—N1112.14 (16)
C7—C12—C13—N16.46 (19)C12—C7—N2—N110.00 (18)
C7—C12—C13—C14176.41 (15)C8—C7—N2—C663.1 (2)
N1—C13—C14—C19171.77 (17)C12—C7—N2—C6174.74 (15)
C12—C13—C14—C195.1 (3)C10—C11—O1—C80.1 (2)
N1—C13—C14—C156.8 (3)C9—C8—O1—C110.1 (2)
C12—C13—C14—C15176.32 (18)C7—C8—O1—C11178.72 (15)
C19—C14—C15—C160.6 (3)

Experimental details

Crystal data
Chemical formulaC19H15ClN2O
Mr322.78
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)5.9247 (14), 8.482 (2), 16.284 (4)
α, β, γ (°)101.424 (3), 90.909 (3), 99.468 (3)
V3)790.2 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.50 × 0.27 × 0.24
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4160, 2886, 2425
Rint0.019
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.126, 1.05
No. of reflections2886
No. of parameters209
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.35

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

 

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