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

Zhang, X.-Y.; Li, X.-Y.; Wang, X.; Fan, X.-S.; Qu, G.-R.

doi:10.1107/S1600536808006156

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o689

doi:10.1107/S1600536808006156

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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 ^* and Gui-Rong Qu ^a

^aSchool of Chemical and Environmental Sciences, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, Xinxiang, Henan 453007, People's Republic of China
^*Correspondence e-mail: xyzh518@sohu.com, xuesen.fan@yahoo.com

(Received 2 March 2008; accepted 5 March 2008; online 12 March 2008)

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, C 2/c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 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

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
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

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

Crystal data top

C₂₀H₁₄N₆O₂	F(000) = 1536
M_r = 370.37	D_x = 1.359 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2825 reflections
a = 16.470 (11) Å	θ = 2.5–21.6°
b = 9.742 (7) Å	µ = 0.09 mm⁻¹
c = 23.46 (2) Å	T = 294 K
β = 105.857 (8)°	Block, yellow
V = 3621 (5) Å³	0.39 × 0.25 × 0.15 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3374 independent reflections
Radiation source: fine-focus sealed tube	2287 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
T_min = 0.945, T_max = 0.986	k = −11→11
13443 measured reflections	l = −28→28

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0546P)² + 1.3917P] where P = (F_o² + 2F_c²)/3
3374 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₀H₁₄N₆O₂	V = 3621 (5) Å³
M_r = 370.37	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 16.470 (11) Å	µ = 0.09 mm⁻¹
b = 9.742 (7) Å	T = 294 K
c = 23.46 (2) Å	0.39 × 0.25 × 0.15 mm
β = 105.857 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3374 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2287 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.986	R_int = 0.027
13443 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.02	Δρ_max = 0.18 e Å⁻³
3374 reflections	Δρ_min = −0.16 e Å⁻³
254 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.14291 (11)	0.3249 (2)	0.22385 (8)	0.0539 (5)
C2	0.13161 (11)	0.17956 (19)	0.22657 (8)	0.0508 (4)
C3	0.12907 (11)	0.06720 (19)	0.18900 (8)	0.0514 (5)
C4	0.11731 (12)	−0.0608 (2)	0.21136 (8)	0.0579 (5)
C5	0.10829 (12)	−0.0751 (2)	0.27046 (8)	0.0586 (5)
C6	0.11882 (11)	0.1536 (2)	0.28254 (8)	0.0515 (5)
C7	0.16473 (14)	0.4076 (2)	0.17675 (9)	0.0675 (6)
H7A	0.1171	0.4109	0.1424	0.101*
H7B	0.2117	0.3663	0.1665	0.101*
H7C	0.1795	0.4992	0.1910	0.101*
C8	0.11094 (16)	−0.1792 (2)	0.17454 (10)	0.0771 (7)
C9	0.13676 (11)	0.08314 (19)	0.12762 (8)	0.0516 (5)
C10	0.06928 (13)	0.1307 (3)	0.08327 (9)	0.0750 (7)
H10	0.0187	0.1510	0.0919	0.090*
C11	0.07559 (14)	0.1485 (2)	0.02644 (9)	0.0749 (7)
H11	0.0300	0.1808	−0.0034	0.090*
C12	0.15017 (13)	0.11769 (19)	0.01483 (8)	0.0573 (5)
C13	0.21832 (13)	0.0685 (2)	0.05755 (9)	0.0656 (6)
H13	0.2684	0.0471	0.0484	0.079*
C14	0.21111 (12)	0.0516 (2)	0.11416 (8)	0.0617 (5)
H14	0.2568	0.0184	0.1437	0.074*
C15	0.11107 (11)	0.3128 (2)	0.36614 (8)	0.0539 (5)
C16	0.14851 (12)	0.2328 (2)	0.41484 (9)	0.0610 (5)
H16	0.1792	0.1550	0.4107	0.073*
C17	0.13988 (13)	0.2697 (2)	0.47001 (9)	0.0674 (6)
H17	0.1640	0.2155	0.5029	0.081*
C18	0.09585 (14)	0.3862 (3)	0.47639 (10)	0.0732 (7)
H18	0.0910	0.4111	0.5136	0.088*
C19	0.05918 (14)	0.4654 (2)	0.42781 (11)	0.0722 (6)
H19	0.0294	0.5440	0.4322	0.087*
C20	0.06610 (12)	0.4293 (2)	0.37226 (10)	0.0636 (5)
H20	0.0408	0.4828	0.3394	0.076*
N1	0.12015 (10)	0.27857 (17)	0.30914 (7)	0.0569 (4)
N2	0.13518 (10)	0.38354 (17)	0.27275 (7)	0.0592 (4)
N3	0.10738 (10)	0.03211 (17)	0.30563 (6)	0.0575 (4)
N4	0.1045 (2)	−0.2721 (2)	0.14393 (10)	0.1197 (9)
N5	0.10113 (12)	−0.20117 (18)	0.29226 (8)	0.0784 (6)
H5A	0.0962	−0.2102	0.3276	0.094*
H5B	0.1015	−0.2726	0.2708	0.094*
N6	0.15858 (14)	0.14160 (19)	−0.04520 (8)	0.0750 (5)
O1	0.22406 (12)	0.1080 (2)	−0.05634 (7)	0.0962 (6)
O2	0.09960 (14)	0.1956 (2)	−0.08097 (7)	0.1125 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0489 (10)	0.0631 (12)	0.0496 (11)	0.0009 (9)	0.0132 (8)	0.0005 (9)
C2	0.0476 (10)	0.0611 (12)	0.0439 (10)	0.0024 (8)	0.0128 (8)	−0.0009 (9)
C3	0.0479 (10)	0.0626 (12)	0.0425 (10)	0.0093 (9)	0.0102 (8)	0.0001 (9)
C4	0.0672 (13)	0.0611 (12)	0.0430 (10)	0.0062 (9)	0.0111 (9)	−0.0021 (9)
C5	0.0655 (12)	0.0633 (13)	0.0455 (11)	−0.0049 (10)	0.0128 (9)	−0.0017 (9)
C6	0.0499 (11)	0.0610 (12)	0.0439 (10)	−0.0028 (9)	0.0135 (8)	−0.0063 (9)
C7	0.0721 (13)	0.0687 (13)	0.0632 (13)	−0.0008 (11)	0.0210 (10)	0.0070 (11)
C8	0.1150 (19)	0.0602 (14)	0.0533 (13)	0.0113 (13)	0.0184 (12)	0.0015 (11)
C9	0.0545 (11)	0.0572 (11)	0.0428 (10)	0.0114 (9)	0.0128 (8)	−0.0004 (8)
C10	0.0606 (13)	0.1155 (19)	0.0501 (11)	0.0348 (12)	0.0173 (10)	0.0073 (12)
C11	0.0726 (14)	0.1049 (18)	0.0449 (11)	0.0368 (13)	0.0120 (10)	0.0089 (11)
C12	0.0760 (13)	0.0552 (11)	0.0441 (10)	0.0137 (10)	0.0221 (9)	−0.0006 (9)
C13	0.0623 (12)	0.0805 (14)	0.0601 (13)	0.0194 (11)	0.0267 (10)	0.0038 (10)
C14	0.0560 (12)	0.0791 (14)	0.0490 (11)	0.0208 (10)	0.0130 (9)	0.0070 (10)
C15	0.0470 (10)	0.0664 (12)	0.0498 (11)	−0.0113 (9)	0.0157 (8)	−0.0135 (9)
C16	0.0535 (11)	0.0732 (13)	0.0557 (12)	−0.0040 (10)	0.0141 (9)	−0.0105 (10)
C17	0.0603 (12)	0.0911 (16)	0.0513 (11)	−0.0140 (11)	0.0161 (9)	−0.0092 (11)
C18	0.0684 (14)	0.0973 (18)	0.0617 (14)	−0.0247 (13)	0.0310 (11)	−0.0278 (13)
C19	0.0646 (13)	0.0787 (15)	0.0832 (17)	−0.0096 (11)	0.0370 (12)	−0.0239 (13)
C20	0.0565 (12)	0.0698 (13)	0.0672 (13)	−0.0063 (10)	0.0216 (10)	−0.0086 (11)
N1	0.0641 (10)	0.0628 (10)	0.0464 (9)	−0.0078 (8)	0.0193 (7)	−0.0086 (8)
N2	0.0627 (10)	0.0615 (10)	0.0540 (10)	−0.0048 (8)	0.0171 (8)	−0.0040 (8)
N3	0.0638 (10)	0.0638 (11)	0.0449 (9)	−0.0083 (8)	0.0151 (7)	−0.0043 (8)
N4	0.206 (3)	0.0672 (14)	0.0819 (15)	0.0173 (16)	0.0322 (16)	−0.0113 (13)
N5	0.1225 (16)	0.0619 (11)	0.0510 (10)	−0.0128 (10)	0.0238 (10)	−0.0003 (8)
N6	0.1076 (16)	0.0713 (12)	0.0516 (10)	0.0168 (11)	0.0311 (11)	0.0007 (9)
O1	0.1160 (14)	0.1135 (14)	0.0769 (11)	0.0135 (11)	0.0567 (11)	0.0013 (10)
O2	0.1504 (18)	0.1383 (16)	0.0511 (9)	0.0640 (14)	0.0312 (10)	0.0233 (10)

Geometric parameters (Å, º) top

C1—N2	1.318 (3)	C12—C13	1.371 (3)
C1—C2	1.431 (3)	C12—N6	1.471 (3)
C1—C7	1.489 (3)	C13—C14	1.375 (3)
C2—C3	1.399 (3)	C13—H13	0.9300
C2—C6	1.408 (3)	C14—H14	0.9300
C3—C4	1.386 (3)	C15—C16	1.381 (3)
C3—C9	1.488 (3)	C15—C20	1.384 (3)
C4—C8	1.428 (3)	C15—N1	1.425 (2)
C4—C5	1.441 (3)	C16—C17	1.387 (3)
C5—N3	1.333 (2)	C16—H16	0.9300
C5—N5	1.348 (3)	C17—C18	1.376 (3)
C6—N3	1.336 (2)	C17—H17	0.9300
C6—N1	1.365 (2)	C18—C19	1.372 (3)
C7—H7A	0.9600	C18—H18	0.9300
C7—H7B	0.9600	C19—C20	1.384 (3)
C7—H7C	0.9600	C19—H19	0.9300
C8—N4	1.142 (3)	C20—H20	0.9300
C9—C10	1.378 (3)	N1—N2	1.397 (2)
C9—C14	1.380 (3)	N5—H5A	0.8600
C10—C11	1.376 (3)	N5—H5B	0.8600
C10—H10	0.9300	N6—O2	1.216 (2)
C11—C12	1.362 (3)	N6—O1	1.222 (2)
C11—H11	0.9300

N2—C1—C2	110.21 (17)	C13—C12—N6	118.86 (19)
N2—C1—C7	120.72 (18)	C12—C13—C14	118.58 (18)
C2—C1—C7	129.00 (18)	C12—C13—H13	120.7
C3—C2—C6	117.42 (18)	C14—C13—H13	120.7
C3—C2—C1	136.70 (18)	C13—C14—C9	120.68 (17)
C6—C2—C1	105.87 (16)	C13—C14—H14	119.7
C4—C3—C2	116.66 (17)	C9—C14—H14	119.7
C4—C3—C9	121.18 (17)	C16—C15—C20	120.50 (19)
C2—C3—C9	122.16 (17)	C16—C15—N1	120.44 (18)
C3—C4—C8	119.51 (18)	C20—C15—N1	119.04 (18)
C3—C4—C5	120.85 (17)	C15—C16—C17	119.3 (2)
C8—C4—C5	119.60 (19)	C15—C16—H16	120.4
N3—C5—N5	117.52 (18)	C17—C16—H16	120.4
N3—C5—C4	122.75 (19)	C18—C17—C16	120.4 (2)
N5—C5—C4	119.73 (18)	C18—C17—H17	119.8
N3—C6—N1	126.23 (17)	C16—C17—H17	119.8
N3—C6—C2	127.62 (17)	C19—C18—C17	119.9 (2)
N1—C6—C2	106.15 (17)	C19—C18—H18	120.0
C1—C7—H7A	109.5	C17—C18—H18	120.0
C1—C7—H7B	109.5	C18—C19—C20	120.5 (2)
H7A—C7—H7B	109.5	C18—C19—H19	119.7
C1—C7—H7C	109.5	C20—C19—H19	119.7
H7A—C7—H7C	109.5	C19—C20—C15	119.4 (2)
H7B—C7—H7C	109.5	C19—C20—H20	120.3
N4—C8—C4	178.2 (3)	C15—C20—H20	120.3
C10—C9—C14	119.01 (18)	C6—N1—N2	110.91 (15)
C10—C9—C3	120.08 (17)	C6—N1—C15	130.13 (16)
C14—C9—C3	120.91 (16)	N2—N1—C15	118.94 (16)
C11—C10—C9	120.98 (19)	C1—N2—N1	106.83 (16)
C11—C10—H10	119.5	C5—N3—C6	114.61 (17)
C9—C10—H10	119.5	C5—N5—H5A	120.0
C12—C11—C10	118.46 (18)	C5—N5—H5B	120.0
C12—C11—H11	120.8	H5A—N5—H5B	120.0
C10—C11—H11	120.8	O2—N6—O1	123.6 (2)
C11—C12—C13	122.28 (18)	O2—N6—C12	117.6 (2)
C11—C12—N6	118.84 (18)	O1—N6—C12	118.81 (19)

N2—C1—C2—C3	176.8 (2)	N6—C12—C13—C14	177.45 (19)
C7—C1—C2—C3	−6.2 (4)	C12—C13—C14—C9	0.1 (3)
N2—C1—C2—C6	−1.8 (2)	C10—C9—C14—C13	0.7 (3)
C7—C1—C2—C6	175.12 (18)	C3—C9—C14—C13	−178.96 (19)
C6—C2—C3—C4	−2.4 (2)	C20—C15—C16—C17	0.6 (3)
C1—C2—C3—C4	179.1 (2)	N1—C15—C16—C17	178.90 (17)
C6—C2—C3—C9	176.39 (16)	C15—C16—C17—C18	−1.2 (3)
C1—C2—C3—C9	−2.1 (3)	C16—C17—C18—C19	0.9 (3)
C2—C3—C4—C8	177.67 (19)	C17—C18—C19—C20	0.0 (3)
C9—C3—C4—C8	−1.1 (3)	C18—C19—C20—C15	−0.5 (3)
C2—C3—C4—C5	0.0 (3)	C16—C15—C20—C19	0.2 (3)
C9—C3—C4—C5	−178.80 (17)	N1—C15—C20—C19	−178.06 (17)
C3—C4—C5—N3	2.7 (3)	N3—C6—N1—N2	178.85 (17)
C8—C4—C5—N3	−174.99 (19)	C2—C6—N1—N2	−1.3 (2)
C3—C4—C5—N5	−176.71 (18)	N3—C6—N1—C15	0.7 (3)
C8—C4—C5—N5	5.6 (3)	C2—C6—N1—C15	−179.46 (17)
C3—C2—C6—N3	2.7 (3)	C16—C15—N1—C6	40.1 (3)
C1—C2—C6—N3	−178.33 (18)	C20—C15—N1—C6	−141.6 (2)
C3—C2—C6—N1	−177.13 (15)	C16—C15—N1—N2	−137.89 (18)
C1—C2—C6—N1	1.82 (19)	C20—C15—N1—N2	40.4 (2)
C3—C4—C8—N4	−45 (11)	C2—C1—N2—N1	1.0 (2)
C5—C4—C8—N4	132 (10)	C7—C1—N2—N1	−176.20 (16)
C4—C3—C9—C10	102.6 (2)	C6—N1—N2—C1	0.2 (2)
C2—C3—C9—C10	−76.2 (3)	C15—N1—N2—C1	178.58 (15)
C4—C3—C9—C14	−77.8 (3)	N5—C5—N3—C6	176.90 (17)
C2—C3—C9—C14	103.5 (2)	C4—C5—N3—C6	−2.5 (3)
C14—C9—C10—C11	−0.9 (3)	N1—C6—N3—C5	179.64 (18)
C3—C9—C10—C11	178.8 (2)	C2—C6—N3—C5	−0.2 (3)
C9—C10—C11—C12	0.2 (4)	C11—C12—N6—O2	4.2 (3)
C10—C11—C12—C13	0.7 (4)	C13—C12—N6—O2	−174.2 (2)
C10—C11—C12—N6	−177.6 (2)	C11—C12—N6—O1	−176.6 (2)
C11—C12—C13—C14	−0.8 (3)	C13—C12—N6—O1	5.1 (3)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, −y, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄N₆O₂
M_r	370.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	16.470 (11), 9.742 (7), 23.46 (2)
β (°)	105.857 (8)
V (Å³)	3621 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.39 × 0.25 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.945, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	13443, 3374, 2287
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.122, 1.02
No. of reflections	3374
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O2ⁱ	0.86	2.13	2.981 (3)	168.3
C14—H14···N2ⁱⁱ	0.93	2.61	3.529 (3)	168.3

Symmetry codes: (i) x, −y, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

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).

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kamal, A. M., Atalla, A. A., Mohamed, T. A. A. & Geies, A. (1991). Z. Naturforsch. Teil B, 46, 541–544. Google Scholar
Quiroga, J., Alvarado, M., Insuasty, B., Moreno, R., Ravina, E., Estevez, I. & de Almedia, R. H. (1999). J. Heterocycl. Chem. 36, 1311–1316. CrossRef CAS Google Scholar
Sekikawa, I., Nishie, J., Tono-oka, S., Tanaka, Y. & Kakimoto, S. (1973). J. Heterocycl. Chem. 10, 931–932. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Straub, A., Stasch, J.-P., Alonso-Alija, C., Benet-Buchholz, J., Ducke, B., Feurer, A. & Furstner, C. (2001). Bioorg. Med. Chem. Lett. 11, 781–784. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zhu, S.-L., Tu, S.-J., Li, T.-J., Zhang, X.-J., Ji, S.-J. & Zhang, Y. (2005). Chin. J. Org. Chem. 25, 987–990. CAS Google Scholar

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Volume 64| Part 4| April 2008| Page o689

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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