Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039462/xu6071sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039462/xu6071Isup2.hkl |
CCDC reference: 296731
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.057
- wR factor = 0.165
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
A dry flask (25 ml) was charged with 5-amino-3-methyl-1-phenylpyrazole (2 mmol), ethyl 2-cyano-3-(4-fluorophenyl)-1-acylate (2 mmol) and 1 ml glycol as energy transfer. The unsealed reaction vessel was put into a modified household microwave oven and connected with refluxing equipment. After microwave irradiation for 5 min (250 W), the reaction mixture was cooled and washed with small amount ethanol. The crude product was filtered and single crystals of (I) were obtained by recrystallization from a 95% ethanol solution (yield 80%). Spectroscopic analysis: IR (KBr, ν, cm−1): 3360, 3074 (NH2), 2228 (CN), 1703 (CO); 1H NMR (300 MHz, DMSO-d6): 2.04 (3H, s, CH3), 4.96–5.18 (1H, m, CH), 4.68–4.77 (1H, m, CH), 7.16–7.81 (9H, m, ArH), 11.30(1H, s, NH).
Methyl H atoms were placed in calculated positions, with C—H = 0.96 Å and torsion angles refined to fit the electron density, with Uiso(H) = 1.5Ueq(C). Other H atoms were placed in idealized positions, with C—H = 0.93 − 0.98 Å and N—H = 0.86 Å, and allowed to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(carrier).
Data collection: SMART (Bruker, 1999); cell refinement: SAINT; data reduction: SAINT (Bruker, 1999); 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.
Fig. 1. The molecular structure of (I), showing 40% probability displacement ellipsoids (arbitrary spheres for H atoms). |
C20H15FN4O | Dx = 1.322 Mg m−3 |
Mr = 346.36 | Melting point = 497–498 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2536 reflections |
a = 10.856 (5) Å | θ = 2.1–21.1° |
b = 8.245 (4) Å | µ = 0.09 mm−1 |
c = 38.898 (17) Å | T = 298 K |
V = 3482 (3) Å3 | Block, colorless |
Z = 8 | 0.45 × 0.41 × 0.35 mm |
F(000) = 1440 |
Bruker SMART CCD area-detector diffractometer | 1712 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.061 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ϕ and ω scans | h = −12→12 |
17020 measured reflections | k = −8→9 |
3069 independent reflections | l = −34→46 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.054P)2 + 3.1712P] where P = (Fo2 + 2Fc2)/3 |
3069 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C20H15FN4O | V = 3482 (3) Å3 |
Mr = 346.36 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.856 (5) Å | µ = 0.09 mm−1 |
b = 8.245 (4) Å | T = 298 K |
c = 38.898 (17) Å | 0.45 × 0.41 × 0.35 mm |
Bruker SMART CCD area-detector diffractometer | 1712 reflections with I > 2σ(I) |
17020 measured reflections | Rint = 0.061 |
3069 independent reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.17 e Å−3 |
3069 reflections | Δρmin = −0.20 e Å−3 |
236 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
F1 | 0.5985 (3) | 0.3427 (4) | 0.49399 (7) | 0.1356 (12) | |
N1 | 0.4743 (2) | 0.1085 (3) | 0.66799 (7) | 0.0479 (7) | |
H1 | 0.4430 | 0.1726 | 0.6831 | 0.058* | |
N2 | 0.2834 (2) | −0.0461 (3) | 0.66026 (7) | 0.0468 (7) | |
N3 | 0.2384 (2) | −0.1592 (3) | 0.63736 (7) | 0.0511 (7) | |
N4 | 0.8660 (3) | 0.0407 (4) | 0.61601 (9) | 0.0696 (9) | |
O1 | 0.6632 (2) | 0.2236 (3) | 0.67158 (6) | 0.0589 (7) | |
C1 | 0.5971 (3) | 0.1169 (4) | 0.66039 (8) | 0.0462 (8) | |
C2 | 0.6450 (2) | −0.0233 (4) | 0.63825 (9) | 0.0463 (8) | |
H2 | 0.6520 | −0.1179 | 0.6534 | 0.056* | |
C3 | 0.5599 (3) | −0.0737 (4) | 0.60773 (8) | 0.0450 (8) | |
H3 | 0.5860 | −0.1817 | 0.6001 | 0.054* | |
C4 | 0.4338 (3) | −0.0907 (4) | 0.62334 (8) | 0.0447 (8) | |
C5 | 0.4001 (3) | −0.0040 (4) | 0.65128 (8) | 0.0443 (8) | |
C6 | 0.3311 (3) | −0.1871 (4) | 0.61542 (9) | 0.0477 (8) | |
C7 | 0.7699 (3) | 0.0152 (4) | 0.62641 (9) | 0.0525 (9) | |
C8 | 0.5677 (3) | 0.0389 (4) | 0.57698 (9) | 0.0472 (8) | |
C9 | 0.6277 (4) | −0.0099 (5) | 0.54775 (10) | 0.0795 (13) | |
H9 | 0.6622 | −0.1131 | 0.5468 | 0.095* | |
C10 | 0.6378 (5) | 0.0929 (7) | 0.51946 (11) | 0.1000 (16) | |
H10 | 0.6781 | 0.0592 | 0.4996 | 0.120* | |
C11 | 0.5878 (4) | 0.2421 (6) | 0.52155 (10) | 0.0813 (13) | |
C12 | 0.5286 (4) | 0.2951 (5) | 0.54961 (10) | 0.0719 (11) | |
H12 | 0.4950 | 0.3989 | 0.5502 | 0.086* | |
C13 | 0.5183 (3) | 0.1936 (4) | 0.57759 (9) | 0.0581 (9) | |
H13 | 0.4774 | 0.2296 | 0.5972 | 0.070* | |
C14 | 0.2059 (3) | 0.0187 (4) | 0.68625 (9) | 0.0489 (8) | |
C15 | 0.0829 (3) | 0.0493 (5) | 0.67888 (10) | 0.0618 (10) | |
H15 | 0.0513 | 0.0240 | 0.6573 | 0.074* | |
C16 | 0.0082 (4) | 0.1170 (6) | 0.70340 (12) | 0.0799 (13) | |
H16 | −0.0749 | 0.1343 | 0.6988 | 0.096* | |
C17 | 0.0563 (4) | 0.1593 (6) | 0.73481 (13) | 0.0911 (15) | |
H17 | 0.0064 | 0.2096 | 0.7511 | 0.109* | |
C18 | 0.1774 (4) | 0.1280 (6) | 0.74243 (11) | 0.0914 (15) | |
H18 | 0.2088 | 0.1552 | 0.7639 | 0.110* | |
C19 | 0.2525 (4) | 0.0561 (5) | 0.71824 (9) | 0.0683 (11) | |
H19 | 0.3342 | 0.0331 | 0.7235 | 0.082* | |
C20 | 0.3188 (3) | −0.3058 (5) | 0.58706 (9) | 0.0667 (11) | |
H20A | 0.2540 | −0.3810 | 0.5923 | 0.100* | |
H20B | 0.3949 | −0.3637 | 0.5843 | 0.100* | |
H20C | 0.2996 | −0.2497 | 0.5661 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.201 (3) | 0.136 (3) | 0.0688 (17) | 0.016 (2) | 0.0285 (19) | 0.0418 (18) |
N1 | 0.0346 (14) | 0.0499 (17) | 0.0592 (18) | −0.0046 (13) | 0.0005 (12) | −0.0043 (14) |
N2 | 0.0359 (14) | 0.0485 (17) | 0.0560 (17) | −0.0087 (13) | −0.0018 (12) | 0.0018 (13) |
N3 | 0.0400 (15) | 0.0506 (18) | 0.0628 (18) | −0.0125 (13) | −0.0065 (14) | 0.0014 (14) |
N4 | 0.0414 (17) | 0.066 (2) | 0.101 (3) | −0.0054 (16) | 0.0015 (17) | 0.0100 (18) |
O1 | 0.0483 (13) | 0.0606 (16) | 0.0679 (16) | −0.0215 (12) | −0.0073 (11) | −0.0004 (13) |
C1 | 0.0380 (18) | 0.049 (2) | 0.052 (2) | −0.0054 (16) | −0.0073 (15) | 0.0135 (16) |
C2 | 0.0297 (16) | 0.0400 (19) | 0.069 (2) | −0.0011 (14) | −0.0055 (15) | 0.0145 (16) |
C3 | 0.0347 (16) | 0.0344 (18) | 0.066 (2) | −0.0003 (14) | 0.0011 (15) | −0.0011 (16) |
C4 | 0.0349 (16) | 0.0435 (19) | 0.056 (2) | −0.0051 (15) | −0.0046 (15) | 0.0039 (16) |
C5 | 0.0306 (16) | 0.045 (2) | 0.057 (2) | −0.0051 (14) | −0.0063 (15) | 0.0077 (17) |
C6 | 0.0386 (17) | 0.045 (2) | 0.059 (2) | −0.0042 (15) | −0.0061 (16) | 0.0054 (17) |
C7 | 0.0363 (19) | 0.048 (2) | 0.074 (2) | −0.0001 (16) | −0.0085 (17) | 0.0060 (18) |
C8 | 0.0363 (17) | 0.047 (2) | 0.058 (2) | −0.0011 (16) | 0.0007 (15) | −0.0040 (17) |
C9 | 0.092 (3) | 0.076 (3) | 0.071 (3) | 0.030 (3) | 0.020 (2) | −0.003 (2) |
C10 | 0.129 (4) | 0.114 (4) | 0.056 (3) | 0.027 (4) | 0.030 (3) | 0.004 (3) |
C11 | 0.105 (3) | 0.086 (3) | 0.053 (3) | 0.003 (3) | 0.005 (2) | 0.021 (2) |
C12 | 0.090 (3) | 0.064 (3) | 0.062 (3) | 0.009 (2) | 0.004 (2) | 0.013 (2) |
C13 | 0.065 (2) | 0.053 (2) | 0.056 (2) | 0.0035 (19) | 0.0079 (18) | 0.0020 (18) |
C14 | 0.0394 (17) | 0.055 (2) | 0.053 (2) | −0.0078 (16) | 0.0052 (15) | 0.0059 (17) |
C15 | 0.0405 (19) | 0.084 (3) | 0.061 (2) | −0.0038 (19) | 0.0048 (17) | 0.008 (2) |
C16 | 0.047 (2) | 0.106 (4) | 0.087 (3) | −0.001 (2) | 0.020 (2) | 0.002 (3) |
C17 | 0.074 (3) | 0.114 (4) | 0.085 (3) | −0.019 (3) | 0.038 (3) | −0.013 (3) |
C18 | 0.080 (3) | 0.133 (4) | 0.061 (3) | −0.028 (3) | 0.012 (2) | −0.011 (3) |
C19 | 0.052 (2) | 0.090 (3) | 0.063 (2) | −0.017 (2) | 0.002 (2) | 0.002 (2) |
C20 | 0.059 (2) | 0.070 (3) | 0.071 (3) | −0.020 (2) | 0.0012 (19) | −0.006 (2) |
F1—C11 | 1.360 (5) | C9—C10 | 1.393 (6) |
N1—C1 | 1.368 (4) | C9—H9 | 0.9300 |
N1—C5 | 1.389 (4) | C10—C11 | 1.347 (6) |
N1—H1 | 0.8600 | C10—H10 | 0.9300 |
N2—C5 | 1.359 (4) | C11—C12 | 1.340 (6) |
N2—N3 | 1.379 (4) | C12—C13 | 1.377 (5) |
N2—C14 | 1.420 (4) | C12—H12 | 0.9300 |
N3—C6 | 1.339 (4) | C13—H13 | 0.9300 |
N4—C7 | 1.139 (4) | C14—C19 | 1.378 (5) |
O1—C1 | 1.216 (4) | C14—C15 | 1.388 (5) |
C1—C2 | 1.532 (5) | C15—C16 | 1.371 (5) |
C2—C7 | 1.466 (4) | C15—H15 | 0.9300 |
C2—C3 | 1.561 (4) | C16—C17 | 1.374 (6) |
C2—H2 | 0.9800 | C16—H16 | 0.9300 |
C3—C4 | 1.503 (4) | C17—C18 | 1.372 (6) |
C3—C8 | 1.516 (5) | C17—H17 | 0.9300 |
C3—H3 | 0.9800 | C18—C19 | 1.379 (5) |
C4—C5 | 1.351 (4) | C18—H18 | 0.9300 |
C4—C6 | 1.403 (4) | C19—H19 | 0.9300 |
C6—C20 | 1.481 (5) | C20—H20A | 0.9600 |
C8—C9 | 1.370 (5) | C20—H20B | 0.9600 |
C8—C13 | 1.385 (5) | C20—H20C | 0.9600 |
C1—N1—C5 | 119.8 (3) | C10—C9—H9 | 119.5 |
C1—N1—H1 | 120.1 | C11—C10—C9 | 118.4 (4) |
C5—N1—H1 | 120.1 | C11—C10—H10 | 120.8 |
C5—N2—N3 | 109.7 (3) | C9—C10—H10 | 120.8 |
C5—N2—C14 | 129.7 (3) | C12—C11—C10 | 122.7 (4) |
N3—N2—C14 | 120.3 (2) | C12—C11—F1 | 118.9 (5) |
C6—N3—N2 | 105.2 (2) | C10—C11—F1 | 118.4 (4) |
O1—C1—N1 | 122.3 (3) | C11—C12—C13 | 119.0 (4) |
O1—C1—C2 | 123.2 (3) | C11—C12—H12 | 120.5 |
N1—C1—C2 | 114.5 (3) | C13—C12—H12 | 120.5 |
C7—C2—C1 | 109.1 (3) | C12—C13—C8 | 121.0 (3) |
C7—C2—C3 | 111.5 (3) | C12—C13—H13 | 119.5 |
C1—C2—C3 | 115.3 (2) | C8—C13—H13 | 119.5 |
C7—C2—H2 | 106.8 | C19—C14—C15 | 119.9 (3) |
C1—C2—H2 | 106.8 | C19—C14—N2 | 120.6 (3) |
C3—C2—H2 | 106.8 | C15—C14—N2 | 119.4 (3) |
C4—C3—C8 | 115.3 (3) | C16—C15—C14 | 120.0 (4) |
C4—C3—C2 | 104.9 (3) | C16—C15—H15 | 120.0 |
C8—C3—C2 | 113.8 (3) | C14—C15—H15 | 120.0 |
C4—C3—H3 | 107.5 | C15—C16—C17 | 119.8 (4) |
C8—C3—H3 | 107.5 | C15—C16—H16 | 120.1 |
C2—C3—H3 | 107.5 | C17—C16—H16 | 120.1 |
C5—C4—C6 | 105.1 (3) | C18—C17—C16 | 120.6 (4) |
C5—C4—C3 | 121.5 (3) | C18—C17—H17 | 119.7 |
C6—C4—C3 | 133.4 (3) | C16—C17—H17 | 119.7 |
C4—C5—N2 | 108.9 (3) | C17—C18—C19 | 120.0 (4) |
C4—C5—N1 | 124.9 (3) | C17—C18—H18 | 120.0 |
N2—C5—N1 | 126.2 (3) | C19—C18—H18 | 120.0 |
N3—C6—C4 | 111.1 (3) | C14—C19—C18 | 119.7 (4) |
N3—C6—C20 | 121.3 (3) | C14—C19—H19 | 120.2 |
C4—C6—C20 | 127.5 (3) | C18—C19—H19 | 120.2 |
N4—C7—C2 | 177.0 (4) | C6—C20—H20A | 109.5 |
C9—C8—C13 | 117.9 (3) | C6—C20—H20B | 109.5 |
C9—C8—C3 | 120.1 (3) | H20A—C20—H20B | 109.5 |
C13—C8—C3 | 121.9 (3) | C6—C20—H20C | 109.5 |
C8—C9—C10 | 121.0 (4) | H20A—C20—H20C | 109.5 |
C8—C9—H9 | 119.5 | H20B—C20—H20C | 109.5 |
C5—N2—N3—C6 | 1.9 (3) | C3—C4—C6—N3 | 179.6 (3) |
C14—N2—N3—C6 | 176.4 (3) | C5—C4—C6—C20 | −179.8 (3) |
C5—N1—C1—O1 | 172.2 (3) | C3—C4—C6—C20 | −0.7 (6) |
C5—N1—C1—C2 | −10.7 (4) | C4—C3—C8—C9 | −132.2 (4) |
O1—C1—C2—C7 | −13.8 (4) | C2—C3—C8—C9 | 106.5 (4) |
N1—C1—C2—C7 | 169.2 (3) | C4—C3—C8—C13 | 49.4 (4) |
O1—C1—C2—C3 | −140.1 (3) | C2—C3—C8—C13 | −71.8 (4) |
N1—C1—C2—C3 | 42.8 (4) | C13—C8—C9—C10 | −0.4 (6) |
C7—C2—C3—C4 | −173.9 (3) | C3—C8—C9—C10 | −178.9 (4) |
C1—C2—C3—C4 | −48.8 (3) | C8—C9—C10—C11 | 0.4 (8) |
C7—C2—C3—C8 | −47.1 (4) | C9—C10—C11—C12 | −0.3 (8) |
C1—C2—C3—C8 | 78.0 (3) | C9—C10—C11—F1 | 179.6 (4) |
C8—C3—C4—C5 | −97.6 (4) | C10—C11—C12—C13 | 0.1 (7) |
C2—C3—C4—C5 | 28.3 (4) | F1—C11—C12—C13 | −179.7 (4) |
C8—C3—C4—C6 | 83.4 (4) | C11—C12—C13—C8 | −0.1 (6) |
C2—C3—C4—C6 | −150.6 (3) | C9—C8—C13—C12 | 0.3 (5) |
C6—C4—C5—N2 | 0.6 (4) | C3—C8—C13—C12 | 178.7 (3) |
C3—C4—C5—N2 | −178.5 (3) | C5—N2—C14—C19 | −41.8 (5) |
C6—C4—C5—N1 | −179.9 (3) | N3—N2—C14—C19 | 144.9 (3) |
C3—C4—C5—N1 | 0.9 (5) | C5—N2—C14—C15 | 136.0 (4) |
N3—N2—C5—C4 | −1.6 (4) | N3—N2—C14—C15 | −37.2 (5) |
C14—N2—C5—C4 | −175.4 (3) | C19—C14—C15—C16 | 0.1 (6) |
N3—N2—C5—N1 | 179.0 (3) | N2—C14—C15—C16 | −177.8 (4) |
C14—N2—C5—N1 | 5.1 (5) | C14—C15—C16—C17 | 2.2 (7) |
C1—N1—C5—C4 | −11.9 (5) | C15—C16—C17—C18 | −2.8 (7) |
C1—N1—C5—N2 | 167.5 (3) | C16—C17—C18—C19 | 1.2 (8) |
N2—N3—C6—C4 | −1.5 (4) | C15—C14—C19—C18 | −1.8 (6) |
N2—N3—C6—C20 | 178.8 (3) | N2—C14—C19—C18 | 176.1 (4) |
C5—C4—C6—N3 | 0.6 (4) | C17—C18—C19—C14 | 1.1 (7) |
Experimental details
Crystal data | |
Chemical formula | C20H15FN4O |
Mr | 346.36 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 298 |
a, b, c (Å) | 10.856 (5), 8.245 (4), 38.898 (17) |
V (Å3) | 3482 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.45 × 0.41 × 0.35 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17020, 3069, 1712 |
Rint | 0.061 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.165, 1.03 |
No. of reflections | 3069 |
No. of parameters | 236 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.20 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
N1—C1 | 1.368 (4) | C2—C3 | 1.561 (4) |
N1—C5 | 1.389 (4) | C3—C4 | 1.503 (4) |
C1—C2 | 1.532 (5) | C4—C5 | 1.351 (4) |
C1—N1—C5 | 119.8 (3) | C4—C3—C8 | 115.3 (3) |
N1—C1—C2 | 114.5 (3) | C4—C3—C2 | 104.9 (3) |
C7—C2—C1 | 109.1 (3) | C8—C3—C2 | 113.8 (3) |
C7—C2—C3 | 111.5 (3) | C5—C4—C3 | 121.5 (3) |
C1—C2—C3 | 115.3 (2) | C4—C5—N1 | 124.9 (3) |
The pyrazolo[3,4-b]pyridine system has many interesting biological and pharmacological properties and is used in the treatment of a wide variety of stress-related illnesses (Sekikawa et al., 1973; Kuczynski et al., 1979; El-Dean et al., 1991). As part of our program aimed at employing microwave irradiation for the preparation of heterocyclic compounds (Tu et al., 2004), we have recently synthesized the title pyrazolo[3,4-b]pyridine derivative, (I), under microwave irradiation and we report here its crystal structure.
The molecular structure of (I) is shown in Fig. 1. The tetrahydropyridine ring adopts a distorted envelope conformation, with atom C1 and C2 deviating from the C3/C4/C5/N1 plane by 0.231 (1) and 0.731 (1) Å, respectively. The dihedral angle of 0.62 (3)° between the C3/C4/C5/N1 plane and the fused pyrazole plane indicates they are coplanar. The pyrazole ring forms a dihedral angle of 39.2 (3)° with the attached phenyl ring.