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Acta Crystallogr Sect E Struct Rep Online. Oct 1, 2012; 68(Pt 10): o3036.
Published online Sep 29, 2012. doi:  10.1107/S1600536812040330
PMCID: PMC3470389
(Z)-3-Methyl-1-phenyl-4-[(p-tol­yl)(p-tolyl­amino)­methyl­idene]-1H-pyrazol-5(4H)-one
Naresh Sharma,a Komal M. Vyas,b R. N. Jadeja,b Rajni Kant,a and Vivek K. Guptaa*
aPost-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
bDepartment of Chemistry, Faculty of Science, The M. S. University of Baroda, Vadodara 390 002, India
Correspondence e-mail: vivek_gupta2k2/at/hotmail.com
Received September 17, 2012; Accepted September 24, 2012.
Abstract
In the title mol­ecule, C25H23N3O2, the pyrazole ring forms dihedral angles of 28.56 (7), 80.35 (7) and 31.99 (7)° with the phenyl ring, the p-tolyl ring and the p-tolyl­amino ring, respectively. The N—H group attached to the exocyclic C=C bond is in a syn arrangement with respect to the C=O bond of the pyrazolone group and an intra­molecular N—H(...)O hydrogen bond is observed. In the crystal, weak C—H(...)π inter­actions link mol­ecules along [100].
Related literature  
For related structures, see: Vyas et al. (2011 [triangle]); Ma et al. (2006 [triangle]); Sun et al. (2007 [triangle]).
An external file that holds a picture, illustration, etc.
Object name is e-68-o3036-scheme1.jpg Object name is e-68-o3036-scheme1.jpg
Crystal data  
  • C25H23N3O
  • M r = 381.46
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o3036-efi1.jpg
  • a = 9.2694 (4) Å
  • b = 18.3156 (8) Å
  • c = 12.6716 (7) Å
  • β = 105.124 (5)°
  • V = 2076.80 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.30 × 0.30 × 0.20 mm
Data collection  
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 [triangle]) T min = 0.914, T max = 1.000
  • 9542 measured reflections
  • 4077 independent reflections
  • 2343 reflections with I > 2σ(I)
  • R int = 0.039
Refinement  
  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.132
  • S = 1.01
  • 4077 reflections
  • 270 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.14 e Å−3
Data collection: CrysAlis PRO (Oxford Diffraction, 2010 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).
Table 1
Table 1
Hydrogen-bond geometry (Å, °)
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812040330/lh5535sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040330/lh5535Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812040330/lh5535Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. VKG is thankful to the University of Jammu, Jammu, for financial support.
supplementary crystallographic information
Comment
The title compound (I) was prepared as a continuation of our studies of the structures 4-toluoyl pyrazolones (Vyas et al., 2011). The molecular structure of (I) is shown in Fig 1. The bond lengths and angles in (I) are normal and correspond to those observed in related structures (Ma et al., 2006; Sun et al., 2007). The pyrazolone ring forms dihedral angles of 28.56 (7)°, 80.35 (7)° and 31.99 (7)° with the phenyl ring (C7—C12) and two benzene rings (C14—C19 and C22—C27). In The N—H group attached to the exocyclic C═C bond (C4-C13) is in a syn arrangement with respect to the C═O bond of the pyrazolone group and an intramolecular N—H···O hydrogen bond is observed. In the crystal, a weak C—H···π interaction link molecules along [100] (Fig .2).
Experimental
Equimolar (10 mmol) ethanolic solution (50 ml) of 5-Methyl-4-(4-methyl-benzoyl)-2-phenyl-2,4-dihydro-pyrazol-3-one and p-toluidine was refluxed for 6 h in round bottom flask, whereupon a microcrystalline yellow precipitate appeared. The product was then isolated and recrystallized from ethanol, and then dried in vacuo to give the title compound in 85% yield. Yellow single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution of the title compound.
Refinement
The H atom bonded to N was located in a difference Fourier map and refined isotropically. The remaining H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.96 Å and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C).
Figures
Fig. 1.
Fig. 1.
The molecular structure of the title compound with ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. The dashed line indicates a hydrogen bond.
Fig. 2.
Fig. 2.
Part of the one-dimensional motif along [100] formed by weak C—H···π interactions (shown as dashed lines).
Crystal data
C25H23N3OF(000) = 808
Mr = 381.46Dx = 1.220 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3374 reflections
a = 9.2694 (4) Åθ = 3.5–29.0°
b = 18.3156 (8) ŵ = 0.08 mm1
c = 12.6716 (7) ÅT = 293 K
β = 105.124 (5)°Block, yellow
V = 2076.80 (17) Å30.30 × 0.30 × 0.20 mm
Z = 4
Data collection
Oxford Diffraction Xcalibur Sapphire3 diffractometer4077 independent reflections
Radiation source: fine-focus sealed tube2343 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 16.1049 pixels mm-1θmax = 26.0°, θmin = 3.5°
ω scansh = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −22→19
Tmin = 0.914, Tmax = 1.000l = −15→12
9542 measured reflections
Refinement
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.132w = 1/[σ2(Fo2) + (0.0435P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
4077 reflectionsΔρmax = 0.17 e Å3
270 parametersΔρmin = −0.14 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0018 (5)
Special details
Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
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
N10.37979 (16)0.27791 (8)0.08898 (14)0.0507 (5)
N20.34012 (18)0.35209 (9)0.07998 (16)0.0566 (5)
C30.1970 (2)0.35428 (11)0.03270 (17)0.0497 (6)
C40.1351 (2)0.28261 (10)0.01024 (16)0.0453 (5)
C50.2589 (2)0.23347 (11)0.04912 (16)0.0466 (5)
O50.26105 (14)0.16518 (7)0.04952 (12)0.0560 (4)
C60.1232 (2)0.42734 (11)0.0119 (2)0.0711 (8)
H6A0.19270.46450.04600.107*
H6B0.03800.42840.04160.107*
H6C0.09140.4361−0.06540.107*
C70.5268 (2)0.25907 (11)0.14877 (18)0.0489 (5)
C80.5900 (2)0.19386 (12)0.12908 (19)0.0588 (6)
H80.53690.16210.07570.071*
C90.7325 (2)0.17612 (13)0.1892 (2)0.0707 (7)
H90.77530.13220.17610.085*
C100.8117 (3)0.22272 (15)0.2681 (2)0.0741 (8)
H100.90720.21020.30890.089*
C110.7492 (2)0.28799 (14)0.28674 (19)0.0656 (7)
H110.80330.31980.33970.079*
C120.6064 (2)0.30674 (12)0.22733 (18)0.0562 (6)
H120.56440.35090.24010.067*
C13−0.0104 (2)0.25866 (11)−0.03560 (16)0.0447 (5)
C14−0.1359 (2)0.31073 (10)−0.07300 (16)0.0426 (5)
C15−0.2309 (2)0.32528 (11)−0.00777 (18)0.0503 (6)
H15−0.21870.30080.05830.060*
C16−0.3446 (2)0.37642 (12)−0.04055 (19)0.0574 (6)
H16−0.40670.38610.00470.069*
C17−0.3674 (2)0.41302 (11)−0.1384 (2)0.0541 (6)
C18−0.2724 (2)0.39762 (12)−0.20344 (18)0.0593 (6)
H18−0.28580.4217−0.26990.071*
C19−0.1579 (2)0.34719 (11)−0.17182 (17)0.0555 (6)
H19−0.09560.3377−0.21700.067*
C20−0.4894 (2)0.46931 (12)−0.1720 (2)0.0826 (9)
H20A−0.57450.4544−0.14740.124*
H20B−0.51760.4739−0.25020.124*
H20C−0.45380.5155−0.13980.124*
N21−0.0338 (2)0.18632 (9)−0.04121 (15)0.0546 (5)
C22−0.1653 (2)0.14481 (11)−0.08416 (18)0.0503 (6)
C23−0.1729 (3)0.07733 (11)−0.03820 (19)0.0636 (7)
H23−0.09400.06120.01860.076*
C24−0.2965 (3)0.03342 (13)−0.0756 (2)0.0750 (8)
H24−0.2995−0.0122−0.04400.090*
C25−0.4156 (3)0.05601 (13)−0.1591 (2)0.0666 (7)
C26−0.4042 (3)0.12227 (13)−0.2062 (2)0.0676 (7)
H26−0.48240.1379−0.26390.081*
C27−0.2809 (2)0.16660 (12)−0.17105 (19)0.0621 (7)
H27−0.27560.2109−0.20570.074*
C28−0.5540 (3)0.00866 (15)−0.1984 (3)0.1072 (11)
H28A−0.59990.0188−0.27410.161*
H28B−0.62350.0192−0.15600.161*
H28C−0.5261−0.0419−0.19000.161*
H210.060 (2)0.1594 (11)−0.0076 (17)0.071 (7)*
Atomic displacement parameters (Å2)
U11U22U33U12U13U23
N10.0428 (9)0.0367 (10)0.0719 (12)0.0019 (8)0.0134 (8)0.0041 (9)
N20.0461 (10)0.0386 (10)0.0830 (13)0.0030 (8)0.0129 (9)0.0032 (9)
C30.0441 (11)0.0432 (13)0.0617 (14)0.0017 (10)0.0135 (10)0.0022 (11)
C40.0409 (10)0.0384 (12)0.0571 (13)0.0009 (9)0.0136 (9)0.0017 (10)
C50.0500 (12)0.0393 (13)0.0524 (13)−0.0001 (10)0.0167 (10)0.0026 (11)
O50.0573 (9)0.0382 (9)0.0702 (10)0.0036 (7)0.0126 (8)0.0043 (8)
C60.0557 (13)0.0414 (13)0.107 (2)0.0041 (11)0.0059 (13)0.0020 (13)
C70.0434 (11)0.0462 (13)0.0589 (14)0.0036 (10)0.0165 (10)0.0100 (11)
C80.0518 (13)0.0508 (14)0.0747 (16)0.0046 (11)0.0183 (11)0.0078 (12)
C90.0602 (15)0.0585 (16)0.093 (2)0.0177 (12)0.0189 (14)0.0180 (15)
C100.0546 (14)0.0829 (19)0.0786 (19)0.0143 (14)0.0063 (13)0.0259 (16)
C110.0580 (14)0.0756 (18)0.0593 (15)−0.0034 (13)0.0084 (12)0.0096 (13)
C120.0522 (12)0.0586 (15)0.0606 (14)0.0035 (11)0.0197 (11)0.0062 (12)
C130.0487 (11)0.0385 (12)0.0502 (12)0.0021 (10)0.0187 (9)0.0016 (10)
C140.0398 (10)0.0402 (12)0.0481 (12)−0.0007 (9)0.0119 (9)−0.0011 (10)
C150.0489 (12)0.0503 (14)0.0540 (13)−0.0028 (10)0.0174 (10)0.0030 (11)
C160.0471 (12)0.0565 (14)0.0725 (16)−0.0016 (11)0.0227 (11)−0.0076 (13)
C170.0439 (12)0.0397 (13)0.0700 (16)−0.0004 (10)−0.0006 (11)−0.0071 (12)
C180.0719 (15)0.0464 (14)0.0547 (14)0.0044 (12)0.0077 (12)0.0075 (12)
C190.0662 (14)0.0516 (14)0.0529 (14)0.0054 (11)0.0228 (11)0.0029 (11)
C200.0592 (15)0.0561 (15)0.116 (2)0.0091 (12)−0.0072 (15)−0.0108 (15)
N210.0467 (10)0.0416 (11)0.0733 (13)−0.0009 (9)0.0117 (9)0.0031 (10)
C220.0532 (12)0.0380 (12)0.0631 (14)−0.0033 (10)0.0211 (11)−0.0037 (11)
C230.0741 (15)0.0430 (14)0.0709 (16)−0.0051 (12)0.0139 (13)−0.0025 (12)
C240.1014 (19)0.0424 (14)0.0863 (18)−0.0170 (14)0.0338 (16)−0.0045 (14)
C250.0684 (15)0.0524 (15)0.0857 (18)−0.0165 (13)0.0324 (14)−0.0247 (14)
C260.0591 (14)0.0579 (16)0.0823 (17)−0.0048 (12)0.0120 (12)−0.0122 (14)
C270.0601 (14)0.0498 (14)0.0724 (16)−0.0072 (11)0.0102 (12)−0.0001 (12)
C280.099 (2)0.089 (2)0.140 (3)−0.0458 (17)0.0429 (19)−0.038 (2)
Geometric parameters (Å, º)
N1—C51.370 (2)C15—H150.9300
N1—N21.404 (2)C16—C171.377 (3)
N1—C71.418 (2)C16—H160.9300
N2—C31.306 (2)C17—C181.383 (3)
C3—C41.431 (3)C17—C201.507 (3)
C3—C61.495 (3)C18—C191.385 (3)
C4—C131.392 (2)C18—H180.9300
C4—C51.440 (2)C19—H190.9300
C5—O51.251 (2)C20—H20A0.9600
C6—H6A0.9600C20—H20B0.9600
C6—H6B0.9600C20—H20C0.9600
C6—H6C0.9600N21—C221.419 (2)
C7—C81.381 (3)N21—H210.99 (2)
C7—C121.384 (3)C22—C231.376 (3)
C8—C91.381 (3)C22—C271.380 (3)
C8—H80.9300C23—C241.378 (3)
C9—C101.372 (3)C23—H230.9300
C9—H90.9300C24—C251.378 (3)
C10—C111.375 (3)C24—H240.9300
C10—H100.9300C25—C261.369 (3)
C11—C121.384 (3)C25—C281.521 (3)
C11—H110.9300C26—C271.378 (3)
C12—H120.9300C26—H260.9300
C13—N211.342 (2)C27—H270.9300
C13—C141.483 (2)C28—H28A0.9600
C14—C151.382 (3)C28—H28B0.9600
C14—C191.386 (3)C28—H28C0.9600
C15—C161.390 (3)
C5—N1—N2111.90 (14)C17—C16—C15121.6 (2)
C5—N1—C7129.18 (16)C17—C16—H16119.2
N2—N1—C7118.26 (15)C15—C16—H16119.2
C3—N2—N1106.27 (15)C16—C17—C18117.72 (19)
N2—C3—C4111.68 (17)C16—C17—C20121.0 (2)
N2—C3—C6118.15 (18)C18—C17—C20121.2 (2)
C4—C3—C6130.17 (17)C17—C18—C19121.5 (2)
C13—C4—C3131.76 (18)C17—C18—H18119.2
C13—C4—C5122.98 (18)C19—C18—H18119.2
C3—C4—C5105.24 (15)C18—C19—C14120.2 (2)
O5—C5—N1125.57 (16)C18—C19—H19119.9
O5—C5—C4129.53 (17)C14—C19—H19119.9
N1—C5—C4104.89 (16)C17—C20—H20A109.5
C3—C6—H6A109.5C17—C20—H20B109.5
C3—C6—H6B109.5H20A—C20—H20B109.5
H6A—C6—H6B109.5C17—C20—H20C109.5
C3—C6—H6C109.5H20A—C20—H20C109.5
H6A—C6—H6C109.5H20B—C20—H20C109.5
H6B—C6—H6C109.5C13—N21—C22131.33 (18)
C8—C7—C12120.25 (18)C13—N21—H21110.9 (11)
C8—C7—N1120.50 (19)C22—N21—H21117.8 (11)
C12—C7—N1119.25 (18)C23—C22—C27118.87 (19)
C9—C8—C7119.6 (2)C23—C22—N21116.91 (18)
C9—C8—H8120.2C27—C22—N21124.16 (19)
C7—C8—H8120.2C22—C23—C24120.5 (2)
C10—C9—C8120.5 (2)C22—C23—H23119.7
C10—C9—H9119.7C24—C23—H23119.7
C8—C9—H9119.7C25—C24—C23121.1 (2)
C9—C10—C11119.8 (2)C25—C24—H24119.5
C9—C10—H10120.1C23—C24—H24119.5
C11—C10—H10120.1C26—C25—C24117.6 (2)
C10—C11—C12120.5 (2)C26—C25—C28121.1 (2)
C10—C11—H11119.7C24—C25—C28121.2 (2)
C12—C11—H11119.7C25—C26—C27122.2 (2)
C7—C12—C11119.3 (2)C25—C26—H26118.9
C7—C12—H12120.3C27—C26—H26118.9
C11—C12—H12120.3C26—C27—C22119.6 (2)
N21—C13—C4117.32 (17)C26—C27—H27120.2
N21—C13—C14121.02 (17)C22—C27—H27120.2
C4—C13—C14121.62 (17)C25—C28—H28A109.5
C15—C14—C19118.75 (19)C25—C28—H28B109.5
C15—C14—C13120.14 (18)H28A—C28—H28B109.5
C19—C14—C13121.09 (19)C25—C28—H28C109.5
C14—C15—C16120.2 (2)H28A—C28—H28C109.5
C14—C15—H15119.9H28B—C28—H28C109.5
C16—C15—H15119.9
C5—N1—N2—C3−1.5 (2)C3—C4—C13—C140.8 (3)
C7—N1—N2—C3−173.05 (18)C5—C4—C13—C14178.85 (19)
N1—N2—C3—C41.1 (2)N21—C13—C14—C1577.8 (3)
N1—N2—C3—C6−179.7 (2)C4—C13—C14—C15−99.8 (2)
N2—C3—C4—C13178.0 (2)N21—C13—C14—C19−104.0 (2)
C6—C3—C4—C13−1.1 (4)C4—C13—C14—C1978.3 (3)
N2—C3—C4—C5−0.4 (2)C19—C14—C15—C16−1.0 (3)
C6—C3—C4—C5−179.4 (2)C13—C14—C15—C16177.19 (17)
N2—N1—C5—O5−178.0 (2)C14—C15—C16—C170.9 (3)
C7—N1—C5—O5−7.6 (4)C15—C16—C17—C18−0.4 (3)
N2—N1—C5—C41.2 (2)C15—C16—C17—C20−178.89 (18)
C7—N1—C5—C4171.6 (2)C16—C17—C18—C190.0 (3)
C13—C4—C5—O50.1 (4)C20—C17—C18—C19178.46 (18)
C3—C4—C5—O5178.6 (2)C17—C18—C19—C14−0.1 (3)
C13—C4—C5—N1−179.07 (19)C15—C14—C19—C180.6 (3)
C3—C4—C5—N1−0.5 (2)C13—C14—C19—C18−177.60 (18)
C5—N1—C7—C833.6 (3)C4—C13—N21—C22−178.6 (2)
N2—N1—C7—C8−156.5 (2)C14—C13—N21—C223.6 (4)
C5—N1—C7—C12−146.3 (2)C13—N21—C22—C23−152.0 (2)
N2—N1—C7—C1223.6 (3)C13—N21—C22—C2730.9 (4)
C12—C7—C8—C90.8 (3)C27—C22—C23—C24−2.4 (4)
N1—C7—C8—C9−179.15 (19)N21—C22—C23—C24−179.6 (2)
C7—C8—C9—C100.0 (4)C22—C23—C24—C25−0.5 (4)
C8—C9—C10—C11−0.7 (4)C23—C24—C25—C262.5 (4)
C9—C10—C11—C120.7 (4)C23—C24—C25—C28−178.2 (2)
C8—C7—C12—C11−0.7 (3)C24—C25—C26—C27−1.6 (4)
N1—C7—C12—C11179.17 (19)C28—C25—C26—C27179.1 (2)
C10—C11—C12—C70.0 (3)C25—C26—C27—C22−1.3 (4)
C3—C4—C13—N21−176.9 (2)C23—C22—C27—C263.3 (4)
C5—C4—C13—N211.2 (3)N21—C22—C27—C26−179.7 (2)
Hydrogen-bond geometry (Å, º)
Cg is the centroid of the C7–C12 ring
D—H···AD—HH···AD···AD—H···A
N21—H21···O50.99 (2)1.82 (2)2.702 (2)146.4 (17)
C15—H15···Cgi0.932.633.470 (2)152
Symmetry code: (i) x−1, y, z.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5535).
References
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