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The title compound, C19H16N4O3, was synthesized by the reaction of 5-amino-3-meth­yl-1-phenyl­pyrazole with 4-nitro­benzaldehyde and Medrum's acid in glycol under microwave irradiation. X-ray crystal structure analysis reveals that the dihydro­pyridine ring adopts a distorted half-chair conformation. In the crystal structure, the mol­ecules exist as N—H...O hydrogen-bonded dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017800/ci6587sup1.cif
Contains datablocks 050518, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017800/ci6587Isup2.hkl
Contains datablock I

CCDC reference: 277222

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.062
  • wR factor = 0.154
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C17 .. 5.02 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

3-methyl-4-(4-nitrophenyl)–6-oxo-1-phenyl-4,5-dihydropyrazolo[3,4-b]pyridine top
Crystal data top
C19H16N4O3F(000) = 728
Mr = 348.36Dx = 1.375 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 2111 reflections
a = 7.846 (5) Åθ = 3.1–27.5°
b = 16.758 (14) ŵ = 0.10 mm1
c = 12.940 (15) ÅT = 193 K
β = 98.374 (12)°Block, yellow
V = 1683 (3) Å30.39 × 0.30 × 0.28 mm
Z = 4
Data collection top
Rigaku Mercury CCD area-detector
diffractometer
3850 independent reflections
Radiation source: fine-focus sealed tube3234 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1010
Absorption correction: multi-scan
(Jacobson, 1998)
k = 2121
Tmin = 0.964, Tmax = 0.974l = 1516
18328 measured reflections
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0624P)2 + 0.765P]
where P = (Fo2 + 2Fc2)/3
3850 reflections(Δ/σ)max = 0.001
240 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.34 e Å3
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
O10.98820 (17)0.54242 (9)0.62102 (10)0.0417 (4)
O20.0742 (3)0.41329 (15)1.02807 (18)0.0916 (7)
O30.3037 (3)0.35734 (11)1.10530 (14)0.0727 (6)
N10.8122 (2)0.44718 (9)0.54238 (11)0.0329 (4)
N20.60602 (19)0.34421 (9)0.47547 (11)0.0311 (3)
N30.44634 (19)0.31740 (10)0.49284 (12)0.0350 (4)
N40.2247 (3)0.39549 (12)1.03321 (15)0.0545 (5)
C10.6614 (2)0.40376 (10)0.54230 (13)0.0286 (4)
C20.5411 (2)0.41689 (11)0.60652 (13)0.0303 (4)
C30.5669 (2)0.48268 (11)0.68675 (14)0.0325 (4)
H30.51160.53220.65420.039*
C40.7619 (2)0.49817 (12)0.71309 (14)0.0386 (5)
H4A0.77890.55000.74980.046*
H4B0.81230.45640.76240.046*
C50.8614 (2)0.49959 (11)0.62127 (14)0.0330 (4)
C60.4090 (2)0.36127 (11)0.57273 (14)0.0333 (4)
C70.6904 (2)0.30902 (10)0.39569 (13)0.0323 (4)
C80.8600 (3)0.28510 (13)0.42012 (16)0.0439 (5)
H80.91710.28910.48990.053*
C90.9465 (3)0.25533 (15)0.34234 (19)0.0545 (6)
H91.06380.23980.35820.065*
C100.8617 (3)0.24841 (14)0.24228 (18)0.0548 (6)
H100.92100.22830.18880.066*
C110.6915 (3)0.27038 (13)0.21863 (15)0.0491 (6)
H110.63380.26450.14920.059*
C120.6036 (3)0.30103 (12)0.29534 (15)0.0399 (5)
H120.48610.31620.27920.048*
C130.2461 (3)0.34548 (14)0.61605 (19)0.0484 (5)
H13A0.18360.30160.57740.073*
H13B0.17430.39360.60930.073*
H13C0.27340.33090.69000.073*
C140.4844 (2)0.46347 (10)0.78336 (14)0.0320 (4)
C150.3325 (2)0.50101 (12)0.79778 (15)0.0378 (4)
H150.28720.54200.75090.045*
C160.2456 (3)0.47983 (13)0.87941 (17)0.0431 (5)
H160.14040.50500.88850.052*
C170.3162 (3)0.42104 (12)0.94724 (15)0.0408 (5)
C180.4689 (3)0.38406 (12)0.93707 (16)0.0448 (5)
H180.51640.34480.98590.054*
C190.5519 (3)0.40544 (12)0.85402 (15)0.0399 (5)
H190.65690.37990.84520.048*
H10.877 (3)0.4487 (15)0.4870 (19)0.054 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0452 (8)0.0457 (8)0.0377 (7)0.0143 (6)0.0178 (6)0.0103 (6)
O20.0799 (14)0.1071 (18)0.1026 (17)0.0087 (12)0.0630 (13)0.0197 (13)
O30.1160 (16)0.0627 (11)0.0485 (10)0.0095 (11)0.0426 (10)0.0127 (9)
N10.0373 (8)0.0352 (8)0.0286 (7)0.0071 (7)0.0128 (6)0.0064 (6)
N20.0340 (8)0.0337 (8)0.0267 (7)0.0028 (6)0.0075 (6)0.0041 (6)
N30.0308 (8)0.0386 (9)0.0358 (8)0.0022 (6)0.0049 (6)0.0033 (7)
N40.0751 (14)0.0463 (11)0.0503 (11)0.0009 (10)0.0371 (10)0.0048 (9)
C10.0324 (9)0.0290 (8)0.0245 (8)0.0014 (7)0.0051 (7)0.0006 (6)
C20.0315 (9)0.0317 (9)0.0282 (8)0.0009 (7)0.0064 (7)0.0000 (7)
C30.0403 (10)0.0300 (9)0.0293 (9)0.0002 (7)0.0126 (7)0.0008 (7)
C40.0443 (11)0.0446 (11)0.0302 (9)0.0107 (9)0.0161 (8)0.0102 (8)
C50.0375 (9)0.0342 (9)0.0291 (9)0.0027 (8)0.0106 (7)0.0035 (7)
C60.0314 (9)0.0351 (9)0.0341 (9)0.0017 (7)0.0068 (7)0.0024 (7)
C70.0435 (10)0.0285 (9)0.0265 (8)0.0031 (7)0.0104 (7)0.0038 (7)
C80.0424 (11)0.0508 (12)0.0389 (10)0.0016 (9)0.0076 (9)0.0100 (9)
C90.0482 (12)0.0608 (14)0.0578 (14)0.0015 (11)0.0184 (11)0.0169 (11)
C100.0708 (16)0.0532 (13)0.0468 (12)0.0082 (12)0.0300 (11)0.0159 (10)
C110.0783 (16)0.0415 (11)0.0284 (10)0.0085 (11)0.0108 (10)0.0073 (8)
C120.0532 (12)0.0350 (10)0.0309 (9)0.0040 (9)0.0042 (8)0.0038 (8)
C130.0334 (10)0.0551 (13)0.0590 (13)0.0064 (9)0.0149 (9)0.0142 (11)
C140.0379 (9)0.0302 (9)0.0299 (9)0.0028 (7)0.0116 (7)0.0045 (7)
C150.0404 (10)0.0378 (10)0.0368 (10)0.0034 (8)0.0105 (8)0.0016 (8)
C160.0399 (10)0.0454 (11)0.0476 (12)0.0034 (9)0.0188 (9)0.0042 (9)
C170.0566 (12)0.0367 (10)0.0345 (10)0.0070 (9)0.0249 (9)0.0056 (8)
C180.0631 (13)0.0359 (10)0.0386 (10)0.0081 (10)0.0186 (10)0.0052 (8)
C190.0463 (11)0.0354 (10)0.0414 (10)0.0101 (8)0.0181 (9)0.0016 (8)
Geometric parameters (Å, º) top
O1—C51.227 (2)C8—C91.386 (3)
O2—N41.210 (3)C8—H80.95
O3—N41.222 (3)C9—C101.372 (4)
N1—C51.359 (2)C9—H90.95
N1—C11.389 (2)C10—C111.376 (3)
N1—H10.94 (2)C10—H100.95
N2—C11.350 (2)C11—C121.387 (3)
N2—N31.380 (2)C11—H110.95
N2—C71.432 (2)C12—H120.95
N3—C61.335 (3)C13—H13A0.98
N4—C171.473 (3)C13—H13B0.98
C1—C21.364 (3)C13—H13C0.98
C2—C61.415 (3)C14—C151.384 (3)
C2—C31.508 (3)C14—C191.386 (3)
C3—C141.523 (3)C15—C161.385 (3)
C3—C41.540 (3)C15—H150.95
C3—H31.00C16—C171.381 (3)
C4—C51.514 (3)C16—H160.95
C4—H4A0.99C17—C181.372 (3)
C4—H4B0.99C18—C191.382 (3)
C6—C131.493 (3)C18—H180.95
C7—C81.382 (3)C19—H190.95
C7—C121.382 (3)
C5—N1—C1119.20 (15)C7—C8—H8120.2
C5—N1—H1115.4 (15)C9—C8—H8120.2
C1—N1—H1124.9 (14)C10—C9—C8119.7 (2)
C1—N2—N3110.59 (14)C10—C9—H9120.2
C1—N2—C7128.79 (16)C8—C9—H9120.2
N3—N2—C7120.62 (15)C9—C10—C11120.6 (2)
C6—N3—N2104.68 (15)C9—C10—H10119.7
O2—N4—O3123.6 (2)C11—C10—H10119.7
O2—N4—C17117.8 (2)C10—C11—C12120.5 (2)
O3—N4—C17118.7 (2)C10—C11—H11119.7
N2—C1—C2108.81 (16)C12—C11—H11119.7
N2—C1—N1125.63 (16)C7—C12—C11118.7 (2)
C2—C1—N1125.49 (16)C7—C12—H12120.7
C1—C2—C6104.26 (16)C11—C12—H12120.7
C1—C2—C3120.13 (16)C6—C13—H13A109.5
C6—C2—C3135.54 (16)C6—C13—H13B109.5
C2—C3—C14112.33 (16)H13A—C13—H13B109.5
C2—C3—C4107.78 (14)C6—C13—H13C109.5
C14—C3—C4112.40 (16)H13A—C13—H13C109.5
C2—C3—H3108.1H13B—C13—H13C109.5
C14—C3—H3108.1C15—C14—C19118.91 (17)
C4—C3—H3108.1C15—C14—C3119.45 (17)
C5—C4—C3115.99 (16)C19—C14—C3121.51 (17)
C5—C4—H4A108.3C14—C15—C16121.06 (19)
C3—C4—H4A108.3C14—C15—H15119.5
C5—C4—H4B108.3C16—C15—H15119.5
C3—C4—H4B108.3C17—C16—C15118.12 (19)
H4A—C4—H4B107.4C17—C16—H16120.9
O1—C5—N1121.19 (16)C15—C16—H16120.9
O1—C5—C4121.47 (16)C18—C17—C16122.43 (18)
N1—C5—C4117.17 (16)C18—C17—N4118.02 (19)
N3—C6—C2111.64 (16)C16—C17—N4119.54 (19)
N3—C6—C13119.31 (17)C17—C18—C19118.30 (19)
C2—C6—C13129.01 (17)C17—C18—H18120.8
C8—C7—C12120.87 (18)C19—C18—H18120.8
C8—C7—N2119.04 (17)C18—C19—C14121.14 (19)
C12—C7—N2120.07 (18)C18—C19—H19119.4
C7—C8—C9119.7 (2)C14—C19—H19119.4
C1—N2—N3—C61.07 (19)N3—N2—C7—C8130.46 (19)
C7—N2—N3—C6178.58 (15)C1—N2—C7—C12129.4 (2)
N3—N2—C1—C20.9 (2)N3—N2—C7—C1251.0 (2)
C7—N2—C1—C2178.66 (17)C12—C7—C8—C92.3 (3)
N3—N2—C1—N1176.16 (16)N2—C7—C8—C9176.18 (19)
C7—N2—C1—N14.2 (3)C7—C8—C9—C101.3 (4)
C5—N1—C1—N2172.89 (17)C8—C9—C10—C110.3 (4)
C5—N1—C1—C210.5 (3)C9—C10—C11—C121.0 (4)
N2—C1—C2—C60.4 (2)C8—C7—C12—C111.7 (3)
N1—C1—C2—C6176.69 (17)N2—C7—C12—C11176.81 (17)
N2—C1—C2—C3177.72 (15)C10—C11—C12—C70.0 (3)
N1—C1—C2—C30.6 (3)C2—C3—C14—C15104.8 (2)
C1—C2—C3—C14149.58 (17)C4—C3—C14—C15133.41 (19)
C6—C2—C3—C1434.2 (3)C2—C3—C14—C1971.0 (2)
C1—C2—C3—C425.2 (2)C4—C3—C14—C1950.8 (2)
C6—C2—C3—C4158.5 (2)C19—C14—C15—C161.9 (3)
C2—C3—C4—C542.6 (2)C3—C14—C15—C16174.05 (18)
C14—C3—C4—C5166.95 (16)C14—C15—C16—C171.1 (3)
C1—N1—C5—O1175.70 (17)C15—C16—C17—C180.8 (3)
C1—N1—C5—C49.0 (3)C15—C16—C17—N4178.32 (18)
C3—C4—C5—O1147.80 (19)O2—N4—C17—C18162.7 (2)
C3—C4—C5—N136.9 (3)O3—N4—C17—C1816.9 (3)
N2—N3—C6—C20.8 (2)O2—N4—C17—C1616.4 (3)
N2—N3—C6—C13177.30 (17)O3—N4—C17—C16163.9 (2)
C1—C2—C6—N30.3 (2)C16—C17—C18—C191.7 (3)
C3—C2—C6—N3176.41 (19)N4—C17—C18—C19177.38 (19)
C1—C2—C6—C13177.6 (2)C17—C18—C19—C140.9 (3)
C3—C2—C6—C135.7 (4)C15—C14—C19—C180.9 (3)
C1—N2—C7—C849.1 (3)C3—C14—C19—C18174.95 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O3i0.992.593.465 (5)148
C12—H12···O3ii0.952.583.285 (4)131
C16—H16···O2iii0.952.533.437 (3)160
N1—H1···O1iv0.94 (2)1.87 (2)2.814 (3)177 (2)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y, z1; (iii) x, y+1, z+2; (iv) x+2, y+1, z+1.
 

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