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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2873.
Published online 2009 October 28. doi:  10.1107/S1600536809043785
PMCID: PMC2971212

4-[1-Acetyl-3-(4-methoxy­phen­yl)-2-pyrazolin-5-yl]phenol

Abstract

In the title compound, C18H18N2O3, the dihedral angle formed by the benzene rings is 71.75 (4)°. In the crystal structure, centrosymmetrically related mol­ecules are linked into dimers by inter­molecular O—H(...)O hydrogen bonds and π–π stacking inter­actions with centroid–centroid distances of 3.5511 (6) Å.

Related literature

For the biological activity of 2-pyrazoline derivatives, see: Grimm et al. (2009 [triangle]). For the synthesis and crystal structure of 2-pyrazoline derivatives, see: Chen et al. (2009 [triangle]); Li et al. (2008 [triangle]); Humaira et al. (2008 [triangle]); Shoman et al. (2009 [triangle]).

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Object name is e-65-o2873-scheme1.jpg

Experimental

Crystal data

  • C18H18N2O3
  • M r = 310.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2873-efi1.jpg
  • a = 8.7037 (17) Å
  • b = 15.673 (3) Å
  • c = 11.096 (2) Å
  • β = 100.31 (3)°
  • V = 1489.2 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 113 K
  • 0.28 × 0.25 × 0.23 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.974, T max = 0.978
  • 12107 measured reflections
  • 3542 independent reflections
  • 2857 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.107
  • S = 1.07
  • 3542 reflections
  • 211 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043785/rz2374sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043785/rz2374Isup2.hkl

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

Acknowledgments

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

supplementary crystallographic information

Comment

The 2-pyrazoline ring system has attracted significant interest in organic and medicinal chemistry over the past several decades. Scaffolds containing the 2-pyrazoline (4,5-dihydropyrazole) heterocycle have demonstrated a wide range of biological activity, including anticancer activity through the inhibition of kinesin spindle protein, CB1 receptor antagonism for obesity, monoamine oxidase inhibition for depression, and a host of other antibacterial, antiviral, and anti-inflammatory activities (Grimm et al., 2009). Some crystal structure of pyrazoline derivatives have been recently reported (Chen et al., 2009; Li et al., 2008). The synthesis and characterization of pyrazoline derivatives was also reported (Humaira et al., 2008; Shoman et al., 2009).

In the molecule of the title compound (Fig. 1), the five-membered 2-pyrazoline ring assumes an envelope conformation, with atom C7 displaced by 0.2690 (11) Å from the mean plane of the N1/N2/C8/C9 atoms. The benzene rings form a dihedral angle of 108.25 (4)°. In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular O—H···.O hydrogen bonds (Table 1) and by a π–π stacking interaction involving the C1–C6 aromatic rings, with a centroid-to-centroid distance of 3.5511 (6) Å.

Experimental

A mixture of 4'-methoxy-4-hydroxychalcone (0.64 g,2.5 mmol) and hydrazine hydrate (1 ml) in acetic acid (15 ml) was refluxed for 2 h. The reaction mixture was then cooled at room temperature, and poured into ice-cold water. The light yellow solid obtained was filtered, washed with water, dichloromethane, and dried. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone/dichloromethane (3:1 v/v) solution at room temperature.

Refinement

H atoms were positioned geometrically (C—H = 0.93–0.98 Å, O—H = 0.82 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C, O) for methyl and hydroxy H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C18H18N2O3F(000) = 656
Mr = 310.34Dx = 1.384 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4953 reflections
a = 8.7037 (17) Åθ = 1.9–27.9°
b = 15.673 (3) ŵ = 0.10 mm1
c = 11.096 (2) ÅT = 113 K
β = 100.31 (3)°Block, colourless
V = 1489.2 (5) Å30.28 × 0.25 × 0.23 mm
Z = 4

Data collection

Rigaku Saturn CCD area-detector diffractometer3542 independent reflections
Radiation source: rotating anode2857 reflections with I > 2σ(I)
confocalRint = 0.035
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.3°
ω and [var phi] scansh = −11→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −20→20
Tmin = 0.974, Tmax = 0.978l = −10→14
12107 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0618P)2 + 0.155P] where P = (Fo2 + 2Fc2)/3
3542 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = −0.22 e Å3

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 > 2σ(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
O10.94883 (10)0.38855 (6)0.70894 (7)0.0229 (2)
H11.04330.37490.71600.034*
O20.75176 (10)0.66339 (5)0.27990 (7)0.0225 (2)
O3−0.11026 (10)0.27148 (5)−0.04411 (8)0.0231 (2)
N10.58975 (11)0.55520 (6)0.21083 (8)0.0167 (2)
N20.43790 (11)0.52531 (6)0.17203 (8)0.0171 (2)
C10.89186 (13)0.40973 (7)0.59032 (10)0.0168 (2)
C20.75202 (13)0.45422 (7)0.56538 (10)0.0182 (2)
H20.69740.46750.62980.022*
C30.69165 (13)0.47942 (7)0.44593 (10)0.0168 (2)
H30.59580.50990.42950.020*
C40.77000 (13)0.46058 (7)0.35034 (9)0.0151 (2)
C50.90875 (13)0.41512 (7)0.37684 (10)0.0163 (2)
H50.96310.40150.31230.020*
C60.97009 (13)0.38908 (7)0.49508 (10)0.0164 (2)
H61.06460.35740.51110.020*
C70.70776 (13)0.48686 (7)0.21887 (10)0.0159 (2)
H70.79570.50530.17800.019*
C80.61163 (13)0.41600 (7)0.14272 (10)0.0171 (2)
H8A0.63860.41130.06000.021*
H8B0.62770.36000.18430.021*
C90.44632 (13)0.44749 (7)0.13665 (9)0.0160 (2)
C100.61741 (14)0.63762 (7)0.24368 (9)0.0179 (2)
C110.47757 (15)0.69509 (8)0.23326 (11)0.0233 (3)
H11A0.51210.75370.25340.035*
H11B0.41070.67590.29030.035*
H11C0.41860.69310.14930.035*
C120.30403 (13)0.39938 (7)0.09013 (9)0.0163 (2)
C130.31003 (14)0.31987 (7)0.03532 (10)0.0183 (2)
H130.40880.29560.03060.022*
C140.17471 (14)0.27499 (7)−0.01279 (10)0.0191 (2)
H140.18120.2213−0.05120.023*
C150.03036 (13)0.30954 (7)−0.00400 (10)0.0180 (2)
C160.02255 (14)0.38880 (7)0.05220 (10)0.0205 (3)
H16−0.07630.41230.05840.025*
C170.15651 (14)0.43316 (8)0.09871 (10)0.0199 (2)
H170.14940.48690.13690.024*
C18−0.11105 (16)0.19636 (9)−0.11600 (13)0.0320 (3)
H18A−0.06430.2087−0.18810.048*
H18B−0.21880.1769−0.14240.048*
H18C−0.05060.1516−0.06710.048*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0209 (5)0.0314 (5)0.0155 (4)0.0013 (4)0.0014 (3)0.0053 (3)
O20.0226 (5)0.0219 (4)0.0217 (4)−0.0016 (3)0.0006 (3)0.0008 (3)
O30.0177 (4)0.0242 (4)0.0269 (4)−0.0011 (3)0.0027 (3)−0.0048 (3)
N10.0146 (5)0.0173 (5)0.0179 (4)0.0021 (4)0.0021 (4)0.0011 (3)
N20.0161 (5)0.0191 (5)0.0158 (4)0.0003 (4)0.0021 (4)0.0015 (4)
C10.0174 (6)0.0167 (5)0.0158 (5)−0.0046 (4)0.0017 (4)0.0015 (4)
C20.0174 (6)0.0216 (6)0.0165 (5)−0.0023 (4)0.0058 (4)−0.0007 (4)
C30.0133 (5)0.0182 (5)0.0190 (5)0.0000 (4)0.0035 (4)−0.0002 (4)
C40.0156 (5)0.0144 (5)0.0150 (5)−0.0021 (4)0.0022 (4)0.0001 (4)
C50.0174 (6)0.0155 (5)0.0168 (5)−0.0007 (4)0.0054 (4)−0.0013 (4)
C60.0141 (6)0.0147 (5)0.0201 (5)−0.0002 (4)0.0020 (4)0.0008 (4)
C70.0154 (5)0.0172 (5)0.0155 (5)0.0033 (4)0.0040 (4)0.0002 (4)
C80.0170 (6)0.0193 (5)0.0148 (5)0.0024 (4)0.0023 (4)−0.0011 (4)
C90.0177 (6)0.0187 (5)0.0118 (5)0.0037 (4)0.0030 (4)0.0018 (4)
C100.0229 (6)0.0177 (5)0.0134 (5)0.0007 (5)0.0037 (4)0.0021 (4)
C110.0261 (6)0.0176 (5)0.0260 (6)0.0033 (5)0.0046 (5)−0.0011 (5)
C120.0176 (6)0.0186 (5)0.0128 (5)0.0017 (4)0.0027 (4)0.0022 (4)
C130.0174 (6)0.0196 (5)0.0184 (5)0.0042 (4)0.0043 (4)0.0007 (4)
C140.0216 (6)0.0171 (5)0.0183 (5)0.0021 (4)0.0030 (4)−0.0009 (4)
C150.0179 (6)0.0212 (6)0.0146 (5)0.0003 (4)0.0019 (4)0.0029 (4)
C160.0177 (6)0.0230 (6)0.0212 (5)0.0041 (5)0.0047 (4)−0.0009 (4)
C170.0210 (6)0.0202 (5)0.0188 (5)0.0041 (5)0.0040 (4)−0.0017 (4)
C180.0253 (7)0.0251 (6)0.0435 (8)−0.0009 (5)0.0008 (6)−0.0114 (6)

Geometric parameters (Å, °)

O1—C11.3619 (13)C8—C91.5112 (15)
O1—H10.8400C8—H8A0.9900
O2—C101.2345 (15)C8—H8B0.9900
O3—C151.3626 (14)C9—C121.4628 (16)
O3—C181.4216 (15)C10—C111.5018 (16)
N1—C101.3521 (15)C11—H11A0.9800
N1—N21.3957 (13)C11—H11B0.9800
N1—C71.4757 (14)C11—H11C0.9800
N2—C91.2873 (14)C12—C131.3917 (15)
C1—C21.3870 (16)C12—C171.4077 (16)
C1—C61.3939 (15)C13—C141.3935 (16)
C2—C31.3927 (16)C13—H130.9500
C2—H20.9500C14—C151.3875 (16)
C3—C41.3915 (15)C14—H140.9500
C3—H30.9500C15—C161.3970 (16)
C4—C51.3876 (16)C16—C171.3762 (17)
C4—C71.5193 (15)C16—H160.9500
C5—C61.3865 (15)C17—H170.9500
C5—H50.9500C18—H18A0.9800
C6—H60.9500C18—H18B0.9800
C7—C81.5474 (16)C18—H18C0.9800
C7—H71.0000
C1—O1—H1109.5N2—C9—C12120.34 (10)
C15—O3—C18117.37 (9)N2—C9—C8113.68 (10)
C10—N1—N2121.13 (9)C12—C9—C8125.91 (10)
C10—N1—C7126.07 (10)O2—C10—N1120.86 (10)
N2—N1—C7112.67 (9)O2—C10—C11122.43 (10)
C9—N2—N1108.04 (9)N1—C10—C11116.71 (10)
O1—C1—C2118.04 (10)C10—C11—H11A109.5
O1—C1—C6122.24 (10)C10—C11—H11B109.5
C2—C1—C6119.72 (10)H11A—C11—H11B109.5
C1—C2—C3120.04 (10)C10—C11—H11C109.5
C1—C2—H2120.0H11A—C11—H11C109.5
C3—C2—H2120.0H11B—C11—H11C109.5
C4—C3—C2120.82 (10)C13—C12—C17118.18 (11)
C4—C3—H3119.6C13—C12—C9121.34 (10)
C2—C3—H3119.6C17—C12—C9120.47 (10)
C5—C4—C3118.30 (10)C12—C13—C14121.61 (10)
C5—C4—C7119.33 (9)C12—C13—H13119.2
C3—C4—C7122.36 (10)C14—C13—H13119.2
C6—C5—C4121.65 (10)C15—C14—C13119.34 (10)
C6—C5—H5119.2C15—C14—H14120.3
C4—C5—H5119.2C13—C14—H14120.3
C5—C6—C1119.44 (10)O3—C15—C14125.30 (11)
C5—C6—H6120.3O3—C15—C16114.99 (10)
C1—C6—H6120.3C14—C15—C16119.69 (11)
N1—C7—C4112.31 (9)C17—C16—C15120.73 (11)
N1—C7—C8100.69 (9)C17—C16—H16119.6
C4—C7—C8113.25 (9)C15—C16—H16119.6
N1—C7—H7110.1C16—C17—C12120.42 (11)
C4—C7—H7110.1C16—C17—H17119.8
C8—C7—H7110.1C12—C17—H17119.8
C9—C8—C7101.97 (9)O3—C18—H18A109.5
C9—C8—H8A111.4O3—C18—H18B109.5
C7—C8—H8A111.4H18A—C18—H18B109.5
C9—C8—H8B111.4O3—C18—H18C109.5
C7—C8—H8B111.4H18A—C18—H18C109.5
H8A—C8—H8B109.2H18B—C18—H18C109.5
C10—N1—N2—C9174.49 (9)N1—N2—C9—C8−2.58 (12)
C7—N1—N2—C9−9.40 (11)C7—C8—C9—N212.40 (12)
O1—C1—C2—C3178.11 (10)C7—C8—C9—C12−170.70 (9)
C6—C1—C2—C3−1.14 (16)N2—N1—C10—O2178.76 (9)
C1—C2—C3—C4−0.03 (17)C7—N1—C10—O23.20 (16)
C2—C3—C4—C50.80 (16)N2—N1—C10—C11−1.45 (14)
C2—C3—C4—C7179.90 (10)C7—N1—C10—C11−177.02 (9)
C3—C4—C5—C6−0.41 (16)N2—C9—C12—C13170.72 (10)
C7—C4—C5—C6−179.55 (10)C8—C9—C12—C13−5.99 (16)
C4—C5—C6—C1−0.73 (16)N2—C9—C12—C17−8.61 (15)
O1—C1—C6—C5−177.70 (10)C8—C9—C12—C17174.68 (10)
C2—C1—C6—C51.51 (16)C17—C12—C13—C141.49 (16)
C10—N1—C7—C471.36 (13)C9—C12—C13—C14−177.86 (10)
N2—N1—C7—C4−104.52 (10)C12—C13—C14—C15−1.19 (16)
C10—N1—C7—C8−167.87 (10)C18—O3—C15—C14−9.49 (16)
N2—N1—C7—C816.25 (10)C18—O3—C15—C16171.96 (10)
C5—C4—C7—N1−162.58 (9)C13—C14—C15—O3−178.16 (10)
C3—C4—C7—N118.32 (15)C13—C14—C15—C160.33 (16)
C5—C4—C7—C884.19 (12)O3—C15—C16—C17178.82 (10)
C3—C4—C7—C8−94.91 (12)C14—C15—C16—C170.18 (17)
N1—C7—C8—C9−15.77 (10)C15—C16—C17—C120.15 (17)
C4—C7—C8—C9104.33 (10)C13—C12—C17—C16−0.96 (16)
N1—N2—C9—C12−179.67 (8)C9—C12—C17—C16178.39 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.841.872.7117 (13)175

Symmetry codes: (i) −x+2, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2374).

References

  • Chen, J., Li, H., Huang, C. & Wu, J. (2009). Acta Cryst. E65, o2147. [PMC free article] [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Grimm, J. B., Wilson, K. J. & Witter, D. J. (2009). J. Org. Chem.74, 6390–6393. [PubMed]
  • Humaira, P., Prince, F. I. & Amir, A. (2008). Synth. Commun.38, 3973–3983.
  • Li, J., Xiao, H.-F. & Yang, J. (2008). Acta Cryst. E64, o1391. [PMC free article] [PubMed]
  • Rigaku/MSC (2005). CrystalClear and CrystalStructure, Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shoman, M. E., Abdel-Aziz, M., Aly, O. M., Farag, H. H. & Morsy, M. A. (2009). Eur. J. Med. Chem.44, 3068–3076. [PubMed]

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