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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2786.
Published online 2010 October 9. doi:  10.1107/S1600536810038912
PMCID: PMC3009137

5-(Anthracen-9-yl)-3-(4-nitro­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazole

Abstract

In the title compound, C29H21N3O2, the five-membered pyrazoline ring is nearly planar, the maximum deviation being 0.037 (3) Å. The anthracene ring system is approximately perpendicular to the central pyrazoline ring, making a dihedral angle of 86.55 (16)°, whereas the two attached benzene rings are oriented at smaller dihedral angles of 12.9 (2) and 14.7 (2)°with respect to the pyrazoline ring. An intra­molecular C—H(...)N hydrogen bond is observed.

Related literature

For applications of pyrazoline derivatives, see: Shaharyar et al. (2006 [triangle]); Christoph et al. (2003 [triangle]); Parmar et al. (1974 [triangle]); Prasad et al. (2005 [triangle]). For a related pyrazoline compound, see: Krishna et al. (1999 [triangle]).

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Object name is e-66-o2786-scheme1.jpg

Experimental

Crystal data

  • C29H21N3O2
  • M r = 443.49
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2786-efi1.jpg
  • a = 23.023 (5) Å
  • b = 10.195 (2) Å
  • c = 9.2005 (18) Å
  • V = 2159.6 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.20 × 0.20 × 0.20 mm

Data collection

  • Rigaku Mercury2 diffractometer
  • 17812 measured reflections
  • 2023 independent reflections
  • 1675 reflections with I > 2σ(I)
  • R int = 0.068

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.095
  • S = 1.08
  • 2023 reflections
  • 308 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL .

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038912/xu5037sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038912/xu5037Isup2.hkl

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

supplementary crystallographic information

Comment

The derivatives of pyrazoline are mostly used in medicine, such as antibacterial (Shaharyar et al., 2006), antidepressant (Prasad et al., 2005) and anticonvulsant (Parmar et al., 1974), furthermore they also have application in cell biological study due to their simple structure and favorable photophysical properties (Christoph et al., 2003). Here we report the structure of the title compound (I), a new derivative of pyrazoline.

In the pyrazoline ring, the bond length of C17=N2 [1.287 (4) Å] indicates a to the normal C=N bond (1.28 Å), while the N2—N3 distance [1.366 (4) Å] agrees with the expected values (Krishna et al., 1999). The mean plane of anthryl ring makes dihedral angles of 84.98 (9) and 82.81 (8)°, with the benzene ring and 4-nitrophenyl group, respectively.

Experimental

3-(9-Anthryl)-1-(4-nitrophenylprop)-2-en-1-one (3 mmol, 1.0 g) and phenylhydrazine (6.5 mmol, 0.7 g) were dissolved in 10 ml acetic acid. The mixture was stirred for 8 h at refluxing temperature to give red solid. The product was isolated and recrystallized from ethanol/ethyl acetate (1:1 v/v) mixed solution, red single-crystal of (1) was obtained.

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C). As no significant anomalous scatterings, Friedel pairs were merged.

Figures

Fig. 1.
Perspective structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C29H21N3O2F(000) = 928
Mr = 443.49Dx = 1.364 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 2023 reflections
a = 23.023 (5) Åθ = 2.6–25.0°
b = 10.195 (2) ŵ = 0.09 mm1
c = 9.2005 (18) ÅT = 293 K
V = 2159.6 (7) Å3Prism, red
Z = 40.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer1675 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.068
graphiteθmax = 25.0°, θmin = 3.1°
Detector resolution: 13.6612 pixels mm-1h = −27→27
CCD_Profile_fitting scansk = −12→12
17812 measured reflectionsl = −10→10
2023 independent 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0418P)2 + 0.3731P] where P = (Fo2 + 2Fc2)/3
2023 reflections(Δ/σ)max < 0.001
308 parametersΔρmax = 0.14 e Å3
2 restraintsΔρmin = −0.16 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 > 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)

xyzUiso*/Ueq
N20.34781 (11)0.8437 (3)0.1581 (3)0.0417 (7)
C180.33011 (15)0.6798 (3)−0.0211 (4)0.0400 (8)
C60.48920 (14)0.7455 (3)0.3722 (4)0.0392 (8)
C70.49683 (14)0.8475 (3)0.2692 (4)0.0380 (8)
C50.53459 (15)0.7161 (3)0.4735 (4)0.0451 (9)
C170.36872 (14)0.7631 (4)0.0641 (4)0.0410 (9)
C210.25650 (16)0.5236 (3)−0.1831 (4)0.0437 (9)
C90.59566 (15)0.8817 (4)0.3653 (4)0.0461 (9)
O10.16551 (13)0.4657 (3)−0.2656 (4)0.0673 (9)
C80.55013 (14)0.9175 (3)0.2655 (4)0.0394 (9)
C150.44934 (13)0.8788 (3)0.1582 (4)0.0408 (8)
H15A0.46190.95490.10130.049*
N30.39237 (12)0.9097 (3)0.2234 (4)0.0434 (7)
C290.42219 (16)1.1131 (3)0.3361 (4)0.0437 (9)
H29A0.45951.10220.29910.052*
C10.43743 (16)0.6694 (3)0.3833 (4)0.0464 (9)
H1A0.40740.68420.31780.056*
C270.35497 (16)1.2377 (4)0.4779 (5)0.0594 (11)
H27A0.34681.30960.53670.071*
C110.65023 (17)0.9509 (4)0.3584 (5)0.0613 (12)
H11A0.68010.92700.42110.074*
C140.56258 (15)1.0242 (3)0.1698 (5)0.0482 (9)
H14A0.53391.05150.10530.058*
C240.37940 (15)1.0216 (3)0.3050 (4)0.0409 (9)
C100.58675 (16)0.7836 (4)0.4662 (4)0.0506 (10)
H10A0.61640.76240.53070.061*
N10.21739 (15)0.4423 (3)−0.2714 (4)0.0558 (9)
C230.35171 (16)0.5779 (4)−0.1053 (5)0.0546 (11)
H23A0.39150.5628−0.10760.066*
C20.43091 (17)0.5761 (4)0.4868 (5)0.0564 (11)
H2A0.39670.52770.49040.068*
C200.23398 (15)0.6237 (4)−0.1030 (4)0.0476 (10)
H20A0.19420.6399−0.10410.057*
O20.23825 (14)0.3550 (3)−0.3453 (4)0.0887 (11)
C280.40961 (17)1.2200 (4)0.4218 (5)0.0509 (10)
H28A0.43851.28100.44190.061*
C120.65894 (18)1.0493 (4)0.2635 (6)0.0689 (13)
H12A0.69461.09210.26050.083*
C160.43391 (13)0.7676 (4)0.0517 (4)0.0453 (9)
H16A0.44610.7885−0.04660.054*
H16B0.45140.68520.08100.054*
C130.61422 (17)1.0873 (4)0.1690 (5)0.0577 (11)
H13A0.62011.15670.10510.069*
C30.47497 (19)0.5511 (4)0.5891 (5)0.0590 (11)
H3A0.46930.48890.66170.071*
C250.32422 (17)1.0409 (4)0.3603 (5)0.0566 (11)
H25A0.29490.98120.33930.068*
C190.27035 (15)0.7011 (3)−0.0203 (4)0.0474 (9)
H19A0.25490.76800.03650.057*
C40.52555 (19)0.6179 (4)0.5811 (5)0.0584 (11)
H4A0.55500.59930.64710.070*
C220.31528 (17)0.4985 (4)−0.1856 (5)0.0572 (11)
H22A0.33010.4294−0.24030.069*
C260.31263 (17)1.1481 (4)0.4460 (6)0.0679 (13)
H26A0.27541.16000.48290.082*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N20.0337 (16)0.0427 (16)0.0487 (18)0.0034 (14)−0.0089 (15)−0.0072 (16)
C180.0364 (18)0.0455 (19)0.038 (2)−0.0010 (16)−0.0049 (17)−0.0013 (18)
C60.0333 (19)0.0358 (18)0.048 (2)0.0078 (15)−0.0037 (16)−0.0067 (18)
C70.0317 (18)0.0382 (18)0.044 (2)0.0055 (15)−0.0054 (16)−0.0067 (18)
C50.046 (2)0.044 (2)0.045 (2)0.0123 (17)−0.0091 (19)−0.005 (2)
C170.0322 (18)0.049 (2)0.041 (2)0.0033 (16)−0.0077 (16)−0.0047 (19)
C210.040 (2)0.052 (2)0.0393 (19)−0.0063 (18)−0.0050 (18)−0.0046 (19)
C90.032 (2)0.054 (2)0.052 (2)0.0026 (17)−0.0061 (17)−0.014 (2)
O10.0474 (17)0.081 (2)0.074 (2)−0.0142 (15)−0.0129 (17)−0.0069 (18)
C80.0347 (19)0.042 (2)0.042 (2)0.0047 (15)−0.0029 (16)−0.0111 (18)
C150.0331 (18)0.044 (2)0.045 (2)0.0027 (15)−0.0080 (17)−0.0037 (19)
N30.0310 (15)0.0459 (17)0.0534 (18)0.0040 (14)−0.0084 (15)−0.0110 (16)
C290.041 (2)0.041 (2)0.049 (2)0.0030 (17)−0.0015 (18)−0.0050 (19)
C10.041 (2)0.042 (2)0.056 (2)0.0045 (17)−0.0084 (19)−0.001 (2)
C270.055 (3)0.052 (2)0.071 (3)0.002 (2)0.005 (2)−0.022 (2)
C110.038 (2)0.074 (3)0.072 (3)0.002 (2)−0.012 (2)−0.015 (3)
C140.040 (2)0.050 (2)0.055 (2)0.0007 (18)0.0018 (19)−0.004 (2)
C240.040 (2)0.0387 (19)0.044 (2)0.0035 (16)−0.0075 (17)−0.0030 (18)
C100.038 (2)0.060 (2)0.054 (3)0.0114 (19)−0.014 (2)−0.012 (2)
N10.054 (2)0.064 (2)0.050 (2)−0.0117 (18)−0.0066 (18)−0.003 (2)
C230.035 (2)0.076 (3)0.053 (2)0.0052 (19)−0.0053 (19)−0.021 (2)
C20.054 (2)0.045 (2)0.071 (3)0.0012 (19)0.001 (2)0.003 (2)
C200.0313 (19)0.055 (2)0.056 (2)0.0010 (17)−0.0054 (19)−0.002 (2)
O20.075 (2)0.097 (2)0.094 (3)−0.007 (2)−0.001 (2)−0.055 (2)
C280.048 (2)0.041 (2)0.064 (3)0.0001 (18)−0.004 (2)−0.005 (2)
C120.048 (3)0.071 (3)0.088 (4)−0.017 (2)0.002 (3)−0.012 (3)
C160.0333 (19)0.059 (2)0.044 (2)0.0019 (17)−0.0053 (17)−0.010 (2)
C130.046 (2)0.060 (3)0.067 (3)−0.009 (2)0.005 (2)−0.007 (2)
C30.071 (3)0.047 (2)0.059 (3)0.013 (2)0.001 (2)0.011 (2)
C250.039 (2)0.056 (2)0.074 (3)−0.0022 (18)0.004 (2)−0.019 (2)
C190.040 (2)0.047 (2)0.055 (2)0.0028 (17)−0.0064 (19)−0.012 (2)
C40.061 (3)0.056 (2)0.058 (3)0.018 (2)−0.011 (2)0.005 (2)
C220.048 (2)0.070 (3)0.053 (2)0.006 (2)−0.002 (2)−0.023 (2)
C260.044 (2)0.073 (3)0.087 (4)0.005 (2)0.013 (2)−0.029 (3)

Geometric parameters (Å, °)

N2—C171.287 (4)C27—C261.368 (5)
N2—N31.366 (4)C27—C281.372 (5)
C18—C231.388 (5)C27—H27A0.9300
C18—C191.393 (5)C11—C121.345 (6)
C18—C171.458 (5)C11—H11A0.9300
C6—C71.417 (5)C14—C131.352 (5)
C6—C11.426 (5)C14—H14A0.9300
C6—C51.432 (5)C24—C251.382 (5)
C7—C81.420 (5)C10—H10A0.9300
C7—C151.530 (5)N1—O21.219 (4)
C5—C101.386 (5)C23—C221.380 (5)
C5—C41.423 (6)C23—H23A0.9300
C17—C161.506 (5)C2—C31.407 (6)
C21—C201.361 (5)C2—H2A0.9300
C21—C221.378 (5)C20—C191.379 (5)
C21—N11.469 (5)C20—H20A0.9300
C9—C101.381 (6)C28—H28A0.9300
C9—C81.440 (5)C12—C131.402 (6)
C9—C111.442 (5)C12—H12A0.9300
O1—N11.219 (4)C16—H16A0.9700
C8—C141.429 (5)C16—H16B0.9700
C15—N31.476 (4)C13—H13A0.9300
C15—C161.540 (5)C3—C41.351 (6)
C15—H15A0.9800C3—H3A0.9300
N3—C241.398 (4)C25—C261.374 (5)
C29—C281.375 (5)C25—H25A0.9300
C29—C241.387 (5)C19—H19A0.9300
C29—H29A0.9300C4—H4A0.9300
C1—C21.354 (5)C22—H22A0.9300
C1—H1A0.9300C26—H26A0.9300
C17—N2—N3109.2 (3)C25—C24—N3120.7 (3)
C23—C18—C19118.3 (3)C29—C24—N3120.5 (3)
C23—C18—C17121.2 (3)C9—C10—C5121.4 (3)
C19—C18—C17120.6 (3)C9—C10—H10A119.3
C7—C6—C1123.4 (3)C5—C10—H10A119.3
C7—C6—C5119.9 (3)O2—N1—O1123.6 (3)
C1—C6—C5116.7 (3)O2—N1—C21118.6 (3)
C6—C7—C8119.5 (3)O1—N1—C21117.8 (3)
C6—C7—C15120.7 (3)C22—C23—C18121.3 (3)
C8—C7—C15119.8 (3)C22—C23—H23A119.3
C10—C5—C4120.7 (4)C18—C23—H23A119.3
C10—C5—C6119.8 (4)C1—C2—C3121.2 (4)
C4—C5—C6119.6 (3)C1—C2—H2A119.4
N2—C17—C18120.4 (3)C3—C2—H2A119.4
N2—C17—C16113.8 (3)C21—C20—C19119.7 (3)
C18—C17—C16125.8 (3)C21—C20—H20A120.1
C20—C21—C22121.5 (3)C19—C20—H20A120.1
C20—C21—N1119.3 (3)C27—C28—C29120.9 (4)
C22—C21—N1119.2 (3)C27—C28—H28A119.6
C10—C9—C8120.3 (3)C29—C28—H28A119.6
C10—C9—C11120.9 (4)C11—C12—C13120.0 (4)
C8—C9—C11118.8 (4)C11—C12—H12A120.0
C7—C8—C14124.8 (3)C13—C12—H12A120.0
C7—C8—C9119.1 (3)C17—C16—C15101.8 (3)
C14—C8—C9116.1 (3)C17—C16—H16A111.4
N3—C15—C7114.1 (3)C15—C16—H16A111.4
N3—C15—C16102.2 (3)C17—C16—H16B111.4
C7—C15—C16115.9 (3)C15—C16—H16B111.4
N3—C15—H15A108.1H16A—C16—H16B109.3
C7—C15—H15A108.1C14—C13—C12120.7 (4)
C16—C15—H15A108.1C14—C13—H13A119.6
N2—N3—C24118.5 (3)C12—C13—H13A119.6
N2—N3—C15112.5 (3)C4—C3—C2119.6 (4)
C24—N3—C15125.6 (3)C4—C3—H3A120.2
C28—C29—C24120.1 (3)C2—C3—H3A120.2
C28—C29—H29A120.0C26—C25—C24120.2 (4)
C24—C29—H29A120.0C26—C25—H25A119.9
C2—C1—C6121.7 (3)C24—C25—H25A119.9
C2—C1—H1A119.1C20—C19—C18120.5 (3)
C6—C1—H1A119.1C20—C19—H19A119.7
C26—C27—C28119.0 (4)C18—C19—H19A119.7
C26—C27—H27A120.5C3—C4—C5121.2 (4)
C28—C27—H27A120.5C3—C4—H4A119.4
C12—C11—C9121.5 (4)C5—C4—H4A119.4
C12—C11—H11A119.2C21—C22—C23118.6 (4)
C9—C11—H11A119.2C21—C22—H22A120.7
C13—C14—C8122.8 (4)C23—C22—H22A120.7
C13—C14—H14A118.6C27—C26—C25121.1 (4)
C8—C14—H14A118.6C27—C26—H26A119.5
C25—C24—C29118.8 (3)C25—C26—H26A119.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1A···N20.932.593.422 (5)150

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5037).

References

  • Christoph, J. F., Liuchun, Y. & Donald, G. V. (2003). J. Am. Chem. Soc 125, 3799–3812. [PubMed]
  • Krishna, R., Velmurugan, D., Murugesan, R., Shanmuga Sundaram, M. & Raghunathan, R. (1999). Acta Cryst. C55, 1676–1677.
  • Parmar, S. S., Pandey, B. R., Dwivedi, C. & Harbinson, R. D. (1974). J. Pharm. Sci.63, 1152–1155. [PubMed]
  • Prasad, Y. R., Rao, A. L., Prasoona, K., Murali, K. & Kumar, P. R. (2005). Bioorg. Med. Chem. Lett.15, 5030–5034. [PubMed]
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Shaharyar, M., Siddiqui, A. A. & Ali, M. A. (2006). Bioorg. Med. Chem. Lett.16, 4571–4574. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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