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The title compound, C21H15N3O2, was synthesized by the reaction of tetronic acid with benzaldehyde and 5-amino-3-methyl-1-phenyl­pyrazole in an aqueous medium under microwave irradition. Its mol­ecular structure shows a planar fused ring system, with the N-bound phenyl ring almost coplanar with it and the C-bound phenyl ring twisted by 63.0 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008999/ci2295sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008999/ci2295Isup2.hkl
Contains datablock I

CCDC reference: 643637

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.069
  • wR factor = 0.156
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 37 Perc.
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.126 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.13 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.31 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 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 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

3-Methyl-1,4-diphenyl-1H,5H,7H-furo[3,4-b]pyrazolo[4,3-e]pyridin-5-one top
Crystal data top
C21H15N3O2F(000) = 712
Mr = 341.36Dx = 1.361 Mg m3
Monoclinic, P21/cMelting point = 489–491 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.067 (4) ÅCell parameters from 883 reflections
b = 22.4393 (12) Åθ = 2.7–21.4°
c = 10.871 (5) ŵ = 0.09 mm1
β = 104.909 (9)°T = 298 K
V = 1665.9 (12) Å3Needle, light-yellow
Z = 40.42 × 0.21 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2941 independent reflections
Radiation source: fine-focus sealed tube1091 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.126
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.963, Tmax = 0.991k = 2626
8562 measured reflectionsl = 1012
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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0338P)2]
where P = (Fo2 + 2Fc2)/3
2941 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. IR: 1752 (CO); 1H NMR: 2.08 (3H, s, CH3), 5.48 (2H, s, CH2), 7.41–7.63 (7H, m, ArH), 8.19 (2H, d, J = 7.6 Hz, ArH).

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
N10.7397 (6)0.63353 (16)0.3565 (3)0.0464 (10)
N21.0425 (5)0.58194 (15)0.4535 (3)0.0432 (10)
N31.1518 (5)0.56675 (16)0.5764 (3)0.0485 (10)
O10.3034 (4)0.70791 (13)0.3836 (3)0.0645 (10)
O20.3184 (5)0.71327 (15)0.5904 (3)0.0715 (11)
C10.8813 (7)0.61332 (19)0.4573 (4)0.0403 (12)
C21.0530 (7)0.58875 (19)0.6534 (4)0.0429 (12)
C30.8832 (7)0.62002 (19)0.5874 (4)0.0394 (12)
C40.7282 (7)0.64968 (18)0.6197 (4)0.0412 (12)
C50.5784 (6)0.66698 (19)0.5165 (4)0.0411 (12)
C60.3984 (7)0.6980 (2)0.5107 (4)0.0534 (14)
C70.4260 (7)0.6877 (2)0.3053 (4)0.0559 (14)
H7A0.46720.72090.26140.067*
H7B0.35670.65920.24250.067*
C80.5966 (7)0.65929 (19)0.3933 (4)0.0437 (12)
C91.1204 (7)0.5651 (2)0.3509 (4)0.0454 (12)
C101.0169 (8)0.5779 (2)0.2239 (4)0.0650 (16)
H100.89580.59680.20600.078*
C111.1003 (8)0.5617 (2)0.1279 (5)0.0723 (17)
H111.03630.57190.04470.087*
C121.2682 (9)0.5322 (2)0.1487 (5)0.0740 (18)
H121.31660.52040.08070.089*
C131.3718 (8)0.5188 (2)0.2731 (5)0.0726 (17)
H131.49230.49960.28920.087*
C141.2914 (8)0.5348 (2)0.3731 (4)0.0597 (14)
H141.35630.52460.45610.072*
C151.1305 (6)0.5776 (2)0.7953 (3)0.0552 (14)
H15A1.25070.55550.81060.083*
H15B1.03590.55520.82560.083*
H15C1.15410.61500.83930.083*
C160.7325 (6)0.66367 (19)0.7553 (4)0.0416 (12)
C170.5936 (6)0.6422 (2)0.8115 (4)0.0534 (14)
H170.49190.61880.76440.064*
C180.6028 (8)0.6547 (2)0.9374 (4)0.0648 (15)
H180.50800.63980.97480.078*
C190.7519 (8)0.6892 (2)1.0067 (4)0.0604 (15)
H190.75820.69741.09150.072*
C200.8935 (7)0.7121 (2)0.9530 (4)0.0579 (14)
H200.99360.73581.00080.070*
C210.8840 (7)0.69913 (19)0.8254 (4)0.0564 (13)
H210.97840.71410.78780.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.042 (3)0.056 (3)0.034 (2)0.003 (2)0.003 (2)0.002 (2)
N20.044 (3)0.053 (3)0.029 (2)0.010 (2)0.0015 (19)0.0023 (19)
N30.040 (2)0.071 (3)0.029 (2)0.011 (2)0.0015 (19)0.008 (2)
O10.056 (2)0.074 (2)0.054 (2)0.018 (2)0.0045 (18)0.0005 (19)
O20.065 (3)0.093 (3)0.051 (2)0.013 (2)0.0069 (19)0.021 (2)
C10.040 (3)0.044 (3)0.035 (3)0.000 (3)0.006 (2)0.000 (2)
C20.039 (3)0.054 (3)0.038 (3)0.003 (3)0.013 (3)0.002 (3)
C30.040 (3)0.053 (3)0.025 (3)0.002 (3)0.007 (2)0.001 (2)
C40.040 (3)0.043 (3)0.036 (3)0.008 (3)0.002 (2)0.000 (2)
C50.033 (3)0.042 (3)0.045 (3)0.002 (3)0.004 (2)0.003 (2)
C60.057 (4)0.057 (4)0.035 (3)0.000 (3)0.009 (3)0.006 (3)
C70.050 (3)0.064 (4)0.046 (3)0.010 (3)0.000 (3)0.001 (3)
C80.040 (3)0.043 (3)0.041 (3)0.002 (3)0.004 (2)0.005 (2)
C90.054 (4)0.049 (3)0.035 (3)0.008 (3)0.014 (3)0.001 (2)
C100.079 (4)0.081 (4)0.032 (3)0.021 (3)0.010 (3)0.001 (3)
C110.083 (5)0.090 (5)0.042 (3)0.024 (4)0.013 (3)0.011 (3)
C120.105 (5)0.082 (4)0.044 (4)0.012 (4)0.034 (3)0.014 (3)
C130.083 (5)0.077 (4)0.068 (4)0.005 (3)0.038 (4)0.018 (3)
C140.069 (4)0.068 (4)0.041 (3)0.013 (3)0.010 (3)0.002 (3)
C150.052 (3)0.083 (4)0.029 (3)0.012 (3)0.007 (2)0.012 (3)
C160.038 (3)0.050 (3)0.036 (3)0.005 (3)0.007 (2)0.001 (2)
C170.041 (3)0.076 (4)0.042 (3)0.014 (3)0.007 (2)0.010 (3)
C180.068 (4)0.085 (4)0.047 (3)0.016 (3)0.026 (3)0.005 (3)
C190.064 (4)0.076 (4)0.038 (3)0.006 (3)0.008 (3)0.009 (3)
C200.056 (4)0.057 (3)0.048 (3)0.002 (3)0.009 (3)0.013 (3)
C210.056 (4)0.059 (3)0.048 (3)0.008 (3)0.002 (2)0.011 (3)
Geometric parameters (Å, º) top
N1—C81.313 (5)C10—H100.93
N1—C11.358 (5)C11—C121.327 (6)
N2—C11.349 (5)C11—H110.93
N2—N31.403 (4)C12—C131.394 (7)
N2—C91.416 (5)C12—H120.93
N3—C21.316 (5)C13—C141.397 (6)
O1—C61.389 (5)C13—H130.93
O1—C71.436 (5)C14—H140.93
O2—C61.200 (5)C15—H15A0.96
C1—C31.418 (5)C15—H15B0.96
C2—C31.416 (5)C15—H15C0.96
C2—C151.519 (5)C16—C171.370 (5)
C3—C41.402 (6)C16—C211.393 (5)
C4—C51.386 (5)C17—C181.383 (5)
C4—C161.500 (5)C17—H170.93
C5—C81.388 (5)C18—C191.367 (6)
C5—C61.437 (6)C18—H180.93
C7—C81.477 (5)C19—C201.380 (6)
C7—H7A0.97C19—H190.93
C7—H7B0.97C20—C211.402 (5)
C9—C141.353 (6)C20—H200.93
C9—C101.415 (5)C21—H210.93
C10—C111.372 (6)
C8—N1—C1111.5 (4)C9—C10—H10120.9
C1—N2—N3111.1 (3)C12—C11—C10122.9 (5)
C1—N2—C9131.8 (4)C12—C11—H11118.6
N3—N2—C9117.1 (4)C10—C11—H11118.6
C2—N3—N2105.2 (4)C11—C12—C13119.7 (5)
C6—O1—C7109.1 (4)C11—C12—H12120.1
N2—C1—N1127.0 (4)C13—C12—H12120.1
N2—C1—C3107.2 (4)C12—C13—C14118.8 (5)
N1—C1—C3125.8 (4)C12—C13—H13120.6
N3—C2—C3112.5 (4)C14—C13—H13120.6
N3—C2—C15118.2 (4)C9—C14—C13120.9 (5)
C3—C2—C15129.3 (4)C9—C14—H14119.5
C4—C3—C2136.3 (4)C13—C14—H14119.5
C4—C3—C1119.5 (4)C2—C15—H15A109.5
C2—C3—C1104.0 (4)C2—C15—H15B109.5
C5—C4—C3114.4 (4)H15A—C15—H15B109.5
C5—C4—C16123.7 (4)C2—C15—H15C109.5
C3—C4—C16121.8 (4)H15A—C15—H15C109.5
C4—C5—C8120.4 (4)H15B—C15—H15C109.5
C4—C5—C6130.9 (4)C17—C16—C21119.7 (4)
C8—C5—C6108.6 (4)C17—C16—C4121.9 (4)
O2—C6—O1118.4 (5)C21—C16—C4118.4 (4)
O2—C6—C5133.0 (5)C16—C17—C18120.9 (4)
O1—C6—C5108.5 (4)C16—C17—H17119.6
O1—C7—C8105.6 (4)C18—C17—H17119.6
O1—C7—H7A110.6C19—C18—C17119.6 (5)
C8—C7—H7A110.6C19—C18—H18120.2
O1—C7—H7B110.6C17—C18—H18120.2
C8—C7—H7B110.6C18—C19—C20121.2 (5)
H7A—C7—H7B108.8C18—C19—H19119.4
N1—C8—C5128.2 (4)C20—C19—H19119.4
N1—C8—C7123.9 (4)C19—C20—C21119.0 (5)
C5—C8—C7108.0 (4)C19—C20—H20120.5
C14—C9—C10119.3 (4)C21—C20—H20120.5
C14—C9—N2120.3 (4)C16—C21—C20119.6 (4)
C10—C9—N2120.4 (4)C16—C21—H21120.2
C11—C10—C9118.2 (5)C20—C21—H21120.2
C11—C10—H10120.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···N10.932.352.988 (6)126
C14—H14···N30.932.382.738 (6)103
C7—H7A···O2i0.972.393.172 (5)137
C20—H20···O2ii0.932.523.427 (6)164
C7—H7B···Cg1iii0.972.753.506 (5)136
C15—H15B···Cg1iv0.962.843.597 (6)137
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y+3/2, z+1/2; (iii) x1, y, z; (iv) x+2, y+3/2, z+3/2.
 

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