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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1732.
Published online 2010 June 23. doi:  10.1107/S1600536810023238
PMCID: PMC3006806

4-[(3,4-Dimeth­oxy­benzyl­idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Abstract

The imino–carbon double-bond in the title Schiff base, C20H21N3O3, has an E configuration; the six-membered aromatic substituent (r.m.s. deviation = 0.012 Å) is nearly coplanar with five-membered pyrazole substituent (r.m.s. deviation = 0.031 Å), the dihedral angle between the two systems being 11.4 (1)°]. The phenyl ring connected to the pyrazole ring is aligned at 45.5 (1)° with respect to this five-membered ring. The N atoms in the ring show pyramidal coordinations.

Related literature

For background literature on Schiff bases derived from 4-amino­anti­pyridine, see: Montalvo-González & Ariza-Castolo (2003 [triangle]).

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Object name is e-66-o1732-scheme1.jpg

Experimental

Crystal data

  • C20H21N3O3
  • M r = 351.40
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1732-efi1.jpg
  • a = 12.5584 (8) Å
  • b = 10.4752 (7) Å
  • c = 14.6002 (9) Å
  • β = 109.039 (1)°
  • V = 1815.6 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.35 × 0.25 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 16900 measured reflections
  • 4164 independent reflections
  • 3442 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.103
  • S = 1.00
  • 4164 reflections
  • 239 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023238/cv2733sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023238/cv2733Isup2.hkl

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

Acknowledgments

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

4-Aminoantipyrine (4-amino-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one) possesses an aminopyrazolone unit, a feature that allows the compound to condense with aromatic aldehydes to yield Schiff bases. The Schiff base derived from the benzaldehyde homolog has nearly coplanar phenyl and pyrazoly rings (Montalvo-González & Ariza-Castolo, 2003). In the title benzaldehyde analog (Scheme I, Fig. 1), the 6-membered ring is nearly coplanar with 5-membered pyrazolyl ring [dihedral angle between the two systems 11.4 (1) °]. The phenyl ring connected to the pyrazolyl ring is aligned at 45.5 (1)°.

Experimental

3,4-Dimethoxybenzaldehyde (0.36 g, 2.2 mmol) and 4-aminoantipyrine (0.45 g, 2.2 mmol) here heated in methanol (15 ml) for 5 h to afford a colorless precipitate. The solid material was collected and recrystallized from methanol.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C–H 0.95 to 0.98 Å, U(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation.

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of C20H21N3O3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C20H21N3O3F(000) = 744
Mr = 351.40Dx = 1.286 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6153 reflections
a = 12.5584 (8) Åθ = 2.4–28.2°
b = 10.4752 (7) ŵ = 0.09 mm1
c = 14.6002 (9) ÅT = 100 K
β = 109.039 (1)°Prism, colourless
V = 1815.6 (2) Å30.35 × 0.25 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer3442 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
graphiteθmax = 27.5°, θmin = 1.7°
ω scansh = −16→16
16900 measured reflectionsk = −13→12
4164 independent reflectionsl = −18→17

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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0548P)2 + 0.5659P] where P = (Fo2 + 2Fc2)/3
4164 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.24 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.28425 (6)0.77513 (8)0.59527 (6)0.01980 (19)
O20.86240 (7)0.62990 (8)0.50221 (6)0.02147 (19)
O30.86452 (8)0.84966 (8)0.42541 (7)0.0292 (2)
N10.26678 (8)0.60441 (9)0.69085 (7)0.0185 (2)
N20.33485 (8)0.50111 (9)0.73701 (7)0.0190 (2)
N30.50498 (8)0.62594 (9)0.60372 (7)0.0187 (2)
C10.18777 (9)0.65675 (11)0.73138 (8)0.0189 (2)
C20.09077 (9)0.71284 (11)0.66951 (9)0.0204 (2)
H20.07780.71550.60170.025*
C30.01286 (10)0.76508 (12)0.70792 (9)0.0235 (3)
H3−0.05300.80520.66620.028*
C40.03033 (10)0.75915 (12)0.80662 (9)0.0252 (3)
H4−0.02400.79360.83230.030*
C50.12751 (11)0.70267 (13)0.86781 (9)0.0258 (3)
H50.13940.69820.93540.031*
C60.20713 (10)0.65278 (12)0.83089 (9)0.0230 (3)
H60.27450.61610.87310.028*
C70.31965 (9)0.67280 (11)0.63587 (8)0.0171 (2)
C80.41934 (9)0.59911 (11)0.64197 (8)0.0173 (2)
C90.42229 (9)0.49573 (11)0.70009 (8)0.0179 (2)
C100.50361 (10)0.38826 (12)0.72347 (9)0.0231 (3)
H10A0.56630.40770.69960.035*
H10B0.46570.31020.69240.035*
H10C0.53260.37590.79380.035*
C110.27490 (10)0.38645 (11)0.75111 (9)0.0225 (3)
H11A0.23430.40540.79650.034*
H11B0.32920.31770.77740.034*
H11C0.22120.35970.68880.034*
C120.49724 (9)0.72136 (11)0.54678 (8)0.0191 (2)
H120.43040.77130.52740.023*
C130.59014 (9)0.75419 (11)0.51128 (8)0.0187 (2)
C140.68242 (9)0.67130 (11)0.52633 (8)0.0182 (2)
H140.68380.59190.55820.022*
C150.77102 (9)0.70504 (11)0.49495 (8)0.0186 (2)
C160.77122 (10)0.82494 (11)0.45064 (9)0.0213 (2)
C170.68007 (11)0.90626 (12)0.43516 (9)0.0241 (3)
H170.67940.98670.40490.029*
C180.58924 (10)0.86946 (11)0.46420 (9)0.0222 (3)
H180.52570.92420.45150.027*
C190.87115 (10)0.51317 (11)0.55464 (9)0.0229 (3)
H19A0.94040.46870.55640.034*
H19B0.80600.45900.52260.034*
H19C0.87300.53160.62090.034*
C200.86692 (15)0.96944 (14)0.37878 (14)0.0452 (4)
H20A0.93810.97750.36520.068*
H20B0.86051.03930.42130.068*
H20C0.80380.97350.31790.068*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0190 (4)0.0167 (4)0.0230 (4)0.0009 (3)0.0060 (3)0.0034 (3)
O20.0217 (4)0.0182 (4)0.0269 (4)0.0041 (3)0.0112 (3)0.0044 (3)
O30.0333 (5)0.0184 (4)0.0463 (6)0.0023 (4)0.0273 (4)0.0066 (4)
N10.0171 (4)0.0173 (5)0.0208 (5)0.0008 (4)0.0060 (4)0.0036 (4)
N20.0183 (4)0.0165 (5)0.0216 (5)0.0006 (4)0.0057 (4)0.0036 (4)
N30.0178 (4)0.0192 (5)0.0192 (5)−0.0019 (4)0.0062 (4)−0.0020 (4)
C10.0170 (5)0.0173 (5)0.0228 (6)−0.0038 (4)0.0071 (4)−0.0013 (5)
C20.0188 (5)0.0214 (6)0.0208 (6)−0.0040 (4)0.0060 (4)−0.0001 (5)
C30.0176 (5)0.0232 (6)0.0293 (6)−0.0018 (5)0.0071 (5)−0.0010 (5)
C40.0241 (6)0.0237 (6)0.0319 (7)−0.0058 (5)0.0147 (5)−0.0083 (5)
C50.0302 (6)0.0271 (7)0.0212 (6)−0.0061 (5)0.0097 (5)−0.0051 (5)
C60.0220 (6)0.0236 (6)0.0211 (6)−0.0021 (5)0.0039 (5)−0.0013 (5)
C70.0164 (5)0.0169 (5)0.0167 (5)−0.0032 (4)0.0038 (4)−0.0016 (4)
C80.0163 (5)0.0172 (5)0.0174 (5)−0.0008 (4)0.0042 (4)−0.0013 (4)
C90.0169 (5)0.0179 (5)0.0170 (5)−0.0012 (4)0.0030 (4)−0.0019 (4)
C100.0232 (6)0.0190 (6)0.0258 (6)0.0036 (5)0.0064 (5)0.0027 (5)
C110.0249 (6)0.0185 (6)0.0251 (6)−0.0033 (5)0.0096 (5)0.0031 (5)
C120.0184 (5)0.0198 (6)0.0189 (5)0.0007 (4)0.0060 (4)−0.0012 (4)
C130.0207 (5)0.0190 (6)0.0171 (5)−0.0008 (4)0.0070 (4)−0.0022 (4)
C140.0219 (5)0.0160 (5)0.0170 (5)−0.0006 (4)0.0069 (4)0.0001 (4)
C150.0206 (5)0.0161 (5)0.0192 (5)0.0017 (4)0.0069 (4)−0.0019 (4)
C160.0250 (6)0.0184 (6)0.0253 (6)−0.0005 (5)0.0149 (5)−0.0008 (5)
C170.0325 (6)0.0166 (6)0.0284 (6)0.0030 (5)0.0169 (5)0.0034 (5)
C180.0256 (6)0.0191 (6)0.0241 (6)0.0046 (5)0.0113 (5)0.0006 (5)
C190.0246 (6)0.0176 (6)0.0273 (6)0.0028 (5)0.0095 (5)0.0041 (5)
C200.0552 (9)0.0222 (7)0.0797 (12)0.0092 (7)0.0513 (9)0.0175 (7)

Geometric parameters (Å, °)

O1—C71.2354 (14)C9—C101.4830 (16)
O2—C151.3669 (14)C10—H10A0.9800
O2—C191.4277 (14)C10—H10B0.9800
O3—C161.3627 (14)C10—H10C0.9800
O3—C201.4326 (16)C11—H11A0.9800
N1—C71.3950 (14)C11—H11B0.9800
N1—N21.4072 (13)C11—H11C0.9800
N1—C11.4206 (15)C12—C131.4638 (16)
N2—C91.3731 (15)C12—H120.9500
N2—C111.4673 (14)C13—C181.3876 (17)
N3—C121.2833 (15)C13—C141.4067 (16)
N3—C81.3926 (14)C14—C151.3804 (16)
C1—C21.3883 (16)C14—H140.9500
C1—C61.3933 (17)C15—C161.4132 (16)
C2—C31.3890 (17)C16—C171.3851 (17)
C2—H20.9500C17—C181.3946 (17)
C3—C41.3865 (18)C17—H170.9500
C3—H30.9500C18—H180.9500
C4—C51.3879 (19)C19—H19A0.9800
C4—H40.9500C19—H19B0.9800
C5—C61.3839 (18)C19—H19C0.9800
C5—H50.9500C20—H20A0.9800
C6—H60.9500C20—H20B0.9800
C7—C81.4486 (15)C20—H20C0.9800
C8—C91.3688 (16)
C15—O2—C19116.78 (9)H10B—C10—H10C109.5
C16—O3—C20116.62 (10)N2—C11—H11A109.5
C7—N1—N2109.98 (9)N2—C11—H11B109.5
C7—N1—C1124.72 (10)H11A—C11—H11B109.5
N2—N1—C1119.67 (9)N2—C11—H11C109.5
C9—N2—N1106.39 (9)H11A—C11—H11C109.5
C9—N2—C11122.28 (10)H11B—C11—H11C109.5
N1—N2—C11115.93 (9)N3—C12—C13120.78 (10)
C12—N3—C8120.78 (10)N3—C12—H12119.6
C2—C1—C6120.57 (11)C13—C12—H12119.6
C2—C1—N1118.44 (10)C18—C13—C14119.19 (11)
C6—C1—N1120.99 (10)C18—C13—C12120.08 (10)
C1—C2—C3119.23 (11)C14—C13—C12120.71 (10)
C1—C2—H2120.4C15—C14—C13120.15 (11)
C3—C2—H2120.4C15—C14—H14119.9
C4—C3—C2120.56 (11)C13—C14—H14119.9
C4—C3—H3119.7O2—C15—C14125.03 (10)
C2—C3—H3119.7O2—C15—C16114.87 (10)
C3—C4—C5119.73 (11)C14—C15—C16120.10 (10)
C3—C4—H4120.1O3—C16—C17125.23 (11)
C5—C4—H4120.1O3—C16—C15115.00 (10)
C6—C5—C4120.37 (12)C17—C16—C15119.77 (11)
C6—C5—H5119.8C16—C17—C18119.66 (11)
C4—C5—H5119.8C16—C17—H17120.2
C5—C6—C1119.50 (11)C18—C17—H17120.2
C5—C6—H6120.2C13—C18—C17121.05 (11)
C1—C6—H6120.2C13—C18—H18119.5
O1—C7—N1123.87 (10)C17—C18—H18119.5
O1—C7—C8131.33 (10)O2—C19—H19A109.5
N1—C7—C8104.77 (9)O2—C19—H19B109.5
C9—C8—N3122.68 (10)H19A—C19—H19B109.5
C9—C8—C7107.92 (10)O2—C19—H19C109.5
N3—C8—C7129.26 (10)H19A—C19—H19C109.5
C8—C9—N2110.34 (10)H19B—C19—H19C109.5
C8—C9—C10128.36 (11)O3—C20—H20A109.5
N2—C9—C10121.31 (10)O3—C20—H20B109.5
C9—C10—H10A109.5H20A—C20—H20B109.5
C9—C10—H10B109.5O3—C20—H20C109.5
H10A—C10—H10B109.5H20A—C20—H20C109.5
C9—C10—H10C109.5H20B—C20—H20C109.5
H10A—C10—H10C109.5
C7—N1—N2—C9−8.00 (12)C7—C8—C9—N2−3.61 (13)
C1—N1—N2—C9−162.78 (10)N3—C8—C9—C10−8.03 (19)
C7—N1—N2—C11−147.65 (10)C7—C8—C9—C10175.83 (11)
C1—N1—N2—C1157.57 (13)N1—N2—C9—C87.08 (12)
C7—N1—C1—C258.12 (15)C11—N2—C9—C8143.54 (11)
N2—N1—C1—C2−151.03 (10)N1—N2—C9—C10−172.41 (10)
C7—N1—C1—C6−121.50 (12)C11—N2—C9—C10−35.94 (16)
N2—N1—C1—C629.34 (16)C8—N3—C12—C13176.26 (10)
C6—C1—C2—C3−0.05 (17)N3—C12—C13—C18−168.62 (11)
N1—C1—C2—C3−179.68 (10)N3—C12—C13—C149.85 (17)
C1—C2—C3—C4−1.31 (18)C18—C13—C14—C150.35 (17)
C2—C3—C4—C51.22 (18)C12—C13—C14—C15−178.13 (10)
C3—C4—C5—C60.25 (19)C19—O2—C15—C14−6.31 (16)
C4—C5—C6—C1−1.59 (19)C19—O2—C15—C16174.22 (10)
C2—C1—C6—C51.50 (18)C13—C14—C15—O2−177.20 (10)
N1—C1—C6—C5−178.89 (11)C13—C14—C15—C162.23 (17)
N2—N1—C7—O1−172.69 (10)C20—O3—C16—C17−0.3 (2)
C1—N1—C7—O1−19.46 (17)C20—O3—C16—C15178.96 (13)
N2—N1—C7—C85.75 (12)O2—C15—C16—O3−2.53 (15)
C1—N1—C7—C8158.98 (10)C14—C15—C16—O3177.98 (11)
C12—N3—C8—C9177.56 (11)O2—C15—C16—C17176.81 (11)
C12—N3—C8—C7−7.18 (18)C14—C15—C16—C17−2.68 (18)
O1—C7—C8—C9176.90 (12)O3—C16—C17—C18179.80 (12)
N1—C7—C8—C9−1.37 (12)C15—C16—C17—C180.52 (19)
O1—C7—C8—N31.1 (2)C14—C13—C18—C17−2.54 (18)
N1—C7—C8—N3−177.18 (11)C12—C13—C18—C17175.95 (11)
N3—C8—C9—N2172.54 (10)C16—C17—C18—C132.10 (19)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2733).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Montalvo-González, R. & Ariza-Castolo, A. (2003). J. Mol. Struct.655, 375–389.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43 Submitted.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography