6-Amino-3-methyl-4-(4-nitro­phen­yl)-1-phenyl­pyrazolo[3,4-b]pyridine-5-carbonitrile

Xin-Ying Zhang; Xiao-Yan Li; Xia Wang; Xue-Sen Fan; Gui-Rong Qu

doi:10.1107/S1600536808006156

. 2008 Mar 12;64(Pt 4):o689. doi: 10.1107/S1600536808006156

6-Amino-3-methyl-4-(4-nitrophenyl)-1-phenylpyrazolo[3,4-b]pyridine-5-carbonitrile

Xin-Ying Zhang ^a,^*, Xiao-Yan Li ^a, Xia Wang ^a, Xue-Sen Fan ^a,^*, Gui-Rong Qu ^a

PMCID: PMC2961049 PMID: 21202081

Abstract

The title compound, C₂₀H₁₄N₆O₂, contains four rings. The dihedral angle between the pyridine ring and the pyrazole ring is 1.9 (1)°, i.e. almost coplanar, which gives rise to a conjugated structure. The dihedral angle between the nitro-substituted phenyl ring and the pyridine ring is 76.3 (1)° and that between the pyrazole ring and the non-substituted phenyl ring is 40.5 (1)°. In the crystal structure, symmetry-related molecules are linked by N—H⋯O and C—H⋯N hydrogen bonds.

Related literature

For related structures, see: Quiroga et al. (1999 ▶); Zhu et al. (2005 ▶). For the biological and pharmacological activities, see: Kamal et al. (1991 ▶); Straub et al. (2001 ▶); Sekikawa et al. (1973 ▶).

Experimental

Crystal data

C₂₀H₁₄N₆O₂
M _r = 370.37
Monoclinic,
a = 16.470 (11) Å
b = 9.742 (7) Å
c = 23.46 (2) Å
β = 105.857 (8)°
V = 3621 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.39 × 0.25 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.945, T _max = 0.986
13443 measured reflections
3374 independent reflections
2287 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.121
S = 1.02
3374 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006156/su2046sup1.cif

e-64-0o689-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006156/su2046Isup2.hkl

e-64-0o689-Isup2.hkl^{(165.6KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯O2ⁱ	0.86	2.13	2.981 (3)	168
C14—H14⋯N2ⁱⁱ	0.93	2.61	3.529 (3)	168

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20772025) and the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 2008 HASTIT006).

supplementary crystallographic information

Comment

The structure of the title compound, (I), is shown below. Dimensions are available in the archived CIF.

For related literature, see Quiroga et al. (1999); Zhu et al. (2005). For the biological and pharmacological activities, see Kamal et al. (1991); Straub et al. (2001); Sekikawa et al. (1973).

Experimental

The title compound was prepared by the following procedure: To 1 ml of 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF₄]) were added 4-nitrobenzaldehyde (1 mmol), malononitrile (1 mmol) and 5-amino-3-methyl-1-phenylpyrazole (1 mmol). The reaction mixture was stirred at 80°C for 10 hrs. The yellow solid product that was obtained was collected by suction and rinsed with water and ethanol (yield 93%). Single crystals of the title compound were obtained by slow evaporation from ethanol.