organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1-[3-(2-Nitro­phen­yl)-5-phenyl-2-pyrazolin-1-yl]ethanone

aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China, and bDepartment of Chemistry & Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: ffjian2008@163.com

(Received 16 May 2010; accepted 31 May 2010; online 5 June 2010)

The title compound, C17H15N3O3, was prepared from 1-(2-nitro­phen­yl)-3-phenyl­prop-2-en-1-one and hydrazine. The dihedral angle between the benzene and phenyl rings is 74.55 (2)°. The pyrazoline ring is in a slight envelope conformation with the C atom bonded to the phenyl ring forming the flap. In the crystal structure, weak inter­molecular C—H⋯O hydrogen bonds connect mol­ecules into chains along [100].

Related literature

For the biological activity of pyrazoline and its derivatives, see: Rawal et al. (1963[Rawal, A. A., Thakor, V. M. & Shah, N. M. (1963). J. Indian Chem. Soc. 40, 323-326.]); Dhal et al. (1975[Dhal, P. N., Acharya, T. E. & Nayak, A. (1975). J. Indian Chem. Soc. 52, 1196-1200.]); Lombardino & Ottemes (1981[Lombardino, G. & Ottemes, I. G. (1981). J. Med. Chem. 24, 830-834.]); Manna et al. (2002[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.]). For related structures, see: Guo et al. (2006[Guo, H.-M., Jian, F.-F., Zhou, L.-Y., Zhao, P.-S. & Zheng, J. (2006). Acta Cryst. E62, o4337-o4338.]); Fahrni et al. (2003[Fahrni, C. J., Yang, L. C. & VanDerveer, D. G. (2003). J. Am. Chem. Soc. 125, 3799-3812.]); Kimura et al. (1977[Kimura, T., Kai, Y., Yasuoka, N. & Kasai, N. (1977). Acta Cryst. B33, 1786-1792.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15N3O3

  • Mr = 309.32

  • Monoclinic, C c

  • a = 6.5064 (13) Å

  • b = 12.385 (3) Å

  • c = 18.752 (4) Å

  • β = 98.26 (3)°

  • V = 1495.4 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.22 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART CCD diffractometer

  • 7203 measured reflections

  • 1710 independent reflections

  • 1354 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.087

  • S = 1.13

  • 1710 reflections

  • 208 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6A⋯O3i 0.93 2.41 3.293 (4) 157
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Pyrazoline and its derivatives are important and useful five-membered heterocyclic compounds, which are found to possess antiviral (Rawal et al., 1963), antifungal (Dhal et al.,1975) and immunosuppressive activities (Lombardino & Ottemes, 1981). 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 herein the crystal structure of the title compound, (I).

In the structure of (I) (Fig. 1), the bond lengths and angles are comparable with those in related structures (Guo et al.,2006; Fahrni et al., 2003; Kimura et al., 1977). The dihehral angle between the benzene and phenyl rings is 74.55 (2)°. The pyrazoline ring is in a slight envelope conformation with atom C13 deviating by 0.158 (4) Å form the essentially planar atoms N1/N2/C14/C15 (rms deviation = 0.003 Å). In the crystal structure, weak intermolecular C—H···O hydrogen bonds connect molecules into chains along [100].

Related literature top

For the biological activity of pyrazoline and its derivatives, see: Rawal et al. (1963); Dhal et al. (1975); Lombardino & Ottemes (1981); Manna et al. (2002). For related structures, see: Guo et al. (2006); Fahrni et al. (2003); Kimura et al. (1977).

Experimental top

3-phenyl-1-(2-nitrophenyl)-2-propen-1-one (0.01 mol) and hydrazine (0.03 mol, 80%) were mixed in acetic acid (30 ml) and stirred under reflux for 6 h; the mixture was then poured into ice-water to afford colourless solids. The solids were filtered off and washed with water until the pH of the solution was about 7.0. Finally, the crystals were dried at room temperature. Single crystals of compound (I) suitable for X-ray measurements were obtained by recrystallization from EtOH at room temperature.

Refinement top

In the absence of anomalous dispersion effects the Freidel pairs were merged. All H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances in the range 0.93–0.98Å and with Uiso=1.2–1.5Ueq.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
1-[3-(2-Nitrophenyl)-5-phenyl-2-pyrazolin-1-yl]ethanone top
Crystal data top
C17H15N3O3F(000) = 648
Mr = 309.32Dx = 1.374 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1354 reflections
a = 6.5064 (13) Åθ = 3.3–27.3°
b = 12.385 (3) ŵ = 0.10 mm1
c = 18.752 (4) ÅT = 293 K
β = 98.26 (3)°Bar, colourless
V = 1495.4 (5) Å30.22 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
1354 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 27.5°, θmin = 3.3°
ϕ and ω scansh = 87
7203 measured reflectionsk = 1616
1710 independent reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0483P)2 + 0.1147P]
where P = (Fo2 + 2Fc2)/3
1710 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.20 e Å3
2 restraintsΔρmin = 0.13 e Å3
Crystal data top
C17H15N3O3V = 1495.4 (5) Å3
Mr = 309.32Z = 4
Monoclinic, CcMo Kα radiation
a = 6.5064 (13) ŵ = 0.10 mm1
b = 12.385 (3) ÅT = 293 K
c = 18.752 (4) Å0.22 × 0.20 × 0.18 mm
β = 98.26 (3)°
Data collection top
Bruker SMART CCD
diffractometer
1354 reflections with I > 2σ(I)
7203 measured reflectionsRint = 0.024
1710 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0302 restraints
wR(F2) = 0.087H-atom parameters constrained
S = 1.13Δρmax = 0.20 e Å3
1710 reflectionsΔρmin = 0.13 e Å3
208 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
C70.1900 (3)0.67920 (17)0.28552 (12)0.0384 (5)
N10.1077 (3)0.79477 (16)0.27976 (10)0.0373 (4)
C120.2478 (3)0.68202 (17)0.36067 (13)0.0381 (5)
N20.2744 (3)0.82918 (16)0.23108 (10)0.0410 (4)
O30.5900 (3)0.90449 (18)0.20896 (11)0.0596 (5)
C150.0046 (3)0.73132 (18)0.24741 (12)0.0376 (5)
C80.3234 (4)0.6223 (2)0.24684 (14)0.0455 (5)
H8A0.29190.61800.19700.055*
N30.1191 (3)0.73560 (17)0.40852 (11)0.0455 (5)
O20.0409 (3)0.69121 (17)0.41903 (11)0.0593 (5)
C170.4397 (4)0.8805 (2)0.25303 (13)0.0408 (5)
C160.4249 (4)0.9042 (2)0.33180 (14)0.0485 (6)
H16A0.54930.93990.34110.073*
H16B0.30750.95020.34640.073*
H16C0.40830.83790.35850.073*
C90.5016 (4)0.5720 (2)0.28093 (17)0.0520 (6)
H9A0.58730.53450.25390.062*
C130.2630 (4)0.7933 (2)0.15621 (12)0.0438 (5)
H13A0.39020.75430.13720.053*
C10.2353 (4)0.8890 (2)0.10825 (11)0.0427 (5)
C20.4070 (4)0.9335 (2)0.06620 (13)0.0505 (6)
H2A0.53630.90120.06520.061*
O10.1846 (4)0.8190 (2)0.43697 (15)0.0842 (8)
C110.4254 (4)0.6332 (2)0.39490 (15)0.0483 (6)
H11A0.45950.63790.44470.058*
C100.5517 (4)0.5776 (2)0.35494 (18)0.0557 (7)
H10A0.67090.54370.37770.067*
C140.0785 (5)0.7133 (2)0.16914 (13)0.0533 (6)
H14A0.12490.63940.16050.064*
H14B0.02540.73000.13850.064*
C60.0422 (4)0.9367 (2)0.10715 (13)0.0503 (6)
H6A0.07540.90710.13420.060*
C50.0242 (5)1.0285 (3)0.06587 (15)0.0595 (7)
H5A0.10521.06030.06570.071*
C30.3884 (5)1.0259 (3)0.02551 (14)0.0614 (7)
H3A0.50541.05600.00150.074*
C40.1966 (5)1.0726 (3)0.02533 (14)0.0633 (8)
H4A0.18361.13400.00220.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C70.0380 (11)0.0305 (11)0.0467 (12)0.0000 (9)0.0063 (10)0.0020 (9)
N10.0378 (10)0.0350 (10)0.0380 (9)0.0039 (8)0.0018 (8)0.0045 (7)
C120.0385 (12)0.0295 (11)0.0452 (11)0.0034 (9)0.0027 (10)0.0010 (9)
N20.0412 (10)0.0440 (11)0.0367 (9)0.0071 (9)0.0013 (8)0.0042 (8)
O30.0403 (10)0.0773 (14)0.0593 (10)0.0098 (9)0.0003 (9)0.0081 (9)
C150.0407 (12)0.0329 (12)0.0389 (11)0.0003 (9)0.0044 (10)0.0005 (9)
C80.0484 (13)0.0356 (13)0.0532 (13)0.0031 (10)0.0097 (11)0.0009 (10)
N30.0442 (11)0.0482 (12)0.0426 (10)0.0021 (10)0.0008 (9)0.0013 (9)
O20.0479 (10)0.0729 (13)0.0590 (11)0.0043 (9)0.0140 (9)0.0091 (9)
C170.0342 (11)0.0398 (13)0.0484 (12)0.0009 (9)0.0063 (10)0.0061 (10)
C160.0465 (13)0.0472 (14)0.0542 (14)0.0025 (11)0.0153 (11)0.0020 (12)
C90.0420 (13)0.0403 (14)0.0751 (18)0.0055 (11)0.0128 (13)0.0027 (12)
C130.0474 (14)0.0434 (13)0.0381 (12)0.0024 (10)0.0030 (10)0.0042 (10)
C10.0454 (13)0.0489 (14)0.0321 (10)0.0046 (10)0.0006 (10)0.0062 (9)
C20.0465 (13)0.0651 (17)0.0378 (11)0.0047 (12)0.0015 (10)0.0027 (11)
O10.0747 (14)0.0793 (16)0.1018 (18)0.0201 (12)0.0239 (13)0.0516 (14)
C110.0477 (14)0.0379 (13)0.0553 (14)0.0013 (11)0.0065 (11)0.0005 (11)
C100.0402 (13)0.0409 (14)0.0829 (19)0.0066 (12)0.0018 (13)0.0042 (13)
C140.0695 (17)0.0472 (15)0.0409 (12)0.0148 (13)0.0004 (12)0.0066 (10)
C60.0459 (14)0.0654 (17)0.0372 (12)0.0006 (13)0.0026 (10)0.0036 (11)
C50.0654 (17)0.0661 (18)0.0475 (13)0.0154 (15)0.0103 (13)0.0063 (13)
C30.0671 (18)0.074 (2)0.0427 (13)0.0159 (16)0.0055 (12)0.0105 (13)
C40.086 (2)0.0612 (19)0.0443 (14)0.0036 (16)0.0155 (15)0.0074 (12)
Geometric parameters (Å, º) top
C7—C81.399 (3)C9—H9A0.9300
C7—C121.406 (3)C13—C11.514 (4)
C7—C151.461 (3)C13—C141.548 (4)
N1—C151.283 (3)C13—H13A0.9800
N1—N21.381 (3)C1—C21.386 (3)
C12—C111.378 (3)C1—C61.392 (4)
C12—N31.471 (3)C2—C31.390 (4)
N2—C171.363 (3)C2—H2A0.9300
N2—C131.484 (3)C11—C101.375 (4)
O3—C171.223 (3)C11—H11A0.9300
C15—C141.506 (3)C10—H10A0.9300
C8—C91.388 (4)C14—H14A0.9700
C8—H8A0.9300C14—H14B0.9700
N3—O11.212 (3)C6—C51.390 (4)
N3—O21.218 (3)C6—H6A0.9300
C17—C161.496 (3)C5—C41.374 (4)
C16—H16A0.9600C5—H5A0.9300
C16—H16B0.9600C3—C41.376 (5)
C16—H16C0.9600C3—H3A0.9300
C9—C101.381 (4)C4—H4A0.9300
C8—C7—C12115.8 (2)N2—C13—H13A109.7
C8—C7—C15120.0 (2)C1—C13—H13A109.7
C12—C7—C15124.2 (2)C14—C13—H13A109.7
C15—N1—N2108.84 (18)C2—C1—C6118.6 (2)
C11—C12—C7122.8 (2)C2—C1—C13119.7 (2)
C11—C12—N3115.2 (2)C6—C1—C13121.7 (2)
C7—C12—N3121.9 (2)C1—C2—C3120.9 (3)
C17—N2—N1121.55 (18)C1—C2—H2A119.5
C17—N2—C13125.0 (2)C3—C2—H2A119.5
N1—N2—C13113.05 (17)C10—C11—C12119.5 (2)
N1—C15—C7121.70 (19)C10—C11—H11A120.2
N1—C15—C14113.7 (2)C12—C11—H11A120.2
C7—C15—C14124.5 (2)C11—C10—C9120.0 (2)
C9—C8—C7121.8 (3)C11—C10—H10A120.0
C9—C8—H8A119.1C9—C10—H10A120.0
C7—C8—H8A119.1C15—C14—C13102.69 (19)
O1—N3—O2124.6 (2)C15—C14—H14A111.2
O1—N3—C12117.3 (2)C13—C14—H14A111.2
O2—N3—C12118.0 (2)C15—C14—H14B111.2
O3—C17—N2119.9 (2)C13—C14—H14B111.2
O3—C17—C16123.5 (2)H14A—C14—H14B109.1
N2—C17—C16116.6 (2)C5—C6—C1120.3 (2)
C17—C16—H16A109.5C5—C6—H6A119.9
C17—C16—H16B109.5C1—C6—H6A119.9
H16A—C16—H16B109.5C4—C5—C6120.4 (3)
C17—C16—H16C109.5C4—C5—H5A119.8
H16A—C16—H16C109.5C6—C5—H5A119.8
H16B—C16—H16C109.5C4—C3—C2119.9 (3)
C10—C9—C8120.1 (2)C4—C3—H3A120.1
C10—C9—H9A120.0C2—C3—H3A120.1
C8—C9—H9A120.0C5—C4—C3120.0 (3)
N2—C13—C1110.74 (19)C5—C4—H4A120.0
N2—C13—C14100.74 (17)C3—C4—H4A120.0
C1—C13—C14116.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O3i0.932.413.293 (4)157
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC17H15N3O3
Mr309.32
Crystal system, space groupMonoclinic, Cc
Temperature (K)293
a, b, c (Å)6.5064 (13), 12.385 (3), 18.752 (4)
β (°) 98.26 (3)
V3)1495.4 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.22 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7203, 1710, 1354
Rint0.024
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.087, 1.13
No. of reflections1710
No. of parameters208
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.13

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O3i0.932.413.293 (4)157
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

This work was supported by the Natural Science Foundation of Shandong Province (No. Y2008B29), P. R. China, and the Yuandu Scholar Fund of Weifang City.

References

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First citationFahrni, C. J., Yang, L. C. & VanDerveer, D. G. (2003). J. Am. Chem. Soc. 125, 3799–3812.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationGuo, H.-M., Jian, F.-F., Zhou, L.-Y., Zhao, P.-S. & Zheng, J. (2006). Acta Cryst. E62, o4337–o4338.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKimura, T., Kai, Y., Yasuoka, N. & Kasai, N. (1977). Acta Cryst. B33, 1786–1792.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationLombardino, G. & Ottemes, I. G. (1981). J. Med. Chem. 24, 830–834.  CrossRef CAS PubMed Web of Science Google Scholar
First citationManna, 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.  Web of Science CrossRef PubMed CAS Google Scholar
First citationRawal, A. A., Thakor, V. M. & Shah, N. M. (1963). J. Indian Chem. Soc. 40, 323–326.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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