6,7-Dihydro-4-(4-methoxy-phen-yl)-3-methyl-6-oxo-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile.

In the title compound, C(21)H(16)N(4)O(2), the dihedral angle between the meth-oxy-substituted benzene ring and the ring system formed by the pyridinone ring and the pyrazole ring is 57.4 (1)°, and that between the unsubstituted phenyl ring and the ring system is 135.6 (1)°. In the crystal structure, mol-ecules are linked together via inter-molecular N-H⋯O hydrogen bonds.

Related literature

For the biological and pharmacological activities of pyrazolo[3,4-b]pyridine derivatives, see Falcó et al. (2005 ▶); Ludwig et al. (2004 ▶). For a related structure, see Quiroga et al. (1999 ▶).

Experimental

Crystal data

C21H16N4O2

M = 356.38

Triclinic,

a = 7.0621 (11) Å

b = 11.0272 (17) Å

c = 12.1743 (19) Å

α = 68.467 (2)°

β = 78.949 (2)°

γ = 87.471 (2)°

V = 865.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 (2) K

0.43 × 0.30 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

6198 measured reflections

3136 independent reflections

2236 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.02

3136 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT (Bruker, 1997 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027852/xu2451sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027852/xu2451Isup2.hkl

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

C21H16N4O2	Z = 2
Mr = 356.38	F(000) = 372
Triclinic, P1	Dx = 1.368 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0621 (11) Å	Cell parameters from 1698 reflections
b = 11.0272 (17) Å	θ = 3.2–26.3°
c = 12.1743 (19) Å	µ = 0.09 mm−1
α = 68.467 (2)°	T = 295 K
β = 78.949 (2)°	Block, colourless
γ = 87.471 (2)°	0.43 × 0.30 × 0.11 mm
V = 865.2 (2) Å3

Bruker SMART CCD area-detector diffractometer	2236 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 25.5°, θmin = 2.9°
φ and ω scans	h = −8→8
6198 measured reflections	k = −13→13
3136 independent reflections	l = −14→14

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) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.1601P] where P = (Fo2 + 2Fc2)/3
3136 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
C1	0.2756 (2)	0.56351 (17)	0.91520 (16)	0.0390 (4)
C2	0.4579 (2)	0.63083 (17)	0.84855 (16)	0.0396 (4)
C3	0.5717 (2)	0.60459 (16)	0.75386 (16)	0.0380 (4)
C4	0.5056 (2)	0.50171 (17)	0.72613 (16)	0.0390 (4)
C5	0.3325 (2)	0.43515 (16)	0.79290 (15)	0.0382 (4)
C6	0.5776 (3)	0.43251 (18)	0.64820 (17)	0.0450 (5)
C7	0.5055 (3)	0.7343 (2)	0.88358 (19)	0.0534 (5)
C8	0.7609 (3)	0.4528 (2)	0.55762 (19)	0.0583 (6)
H8A	0.7738	0.3832	0.5273	0.087*
H8B	0.8686	0.4537	0.5950	0.087*
H8C	0.7580	0.5345	0.4924	0.087*
C9	0.1563 (3)	0.23971 (18)	0.79607 (16)	0.0457 (5)
C10	−0.0341 (3)	0.2728 (2)	0.81733 (18)	0.0549 (5)
H10	−0.0665	0.3585	0.8065	0.066*
C11	−0.1762 (3)	0.1761 (3)	0.8550 (2)	0.0736 (7)
H11	−0.3052	0.1966	0.8713	0.088*
C12	−0.1284 (5)	0.0504 (3)	0.8685 (2)	0.0857 (9)
H12	−0.2250	−0.0137	0.8923	0.103*
C13	0.0630 (5)	0.0186 (2)	0.8470 (2)	0.0813 (8)
H13	0.0947	−0.0670	0.8567	0.098*
C14	0.2069 (3)	0.1128 (2)	0.81120 (19)	0.0623 (6)
H14	0.3360	0.0915	0.7975	0.075*
C15	0.7532 (2)	0.68056 (16)	0.68722 (16)	0.0386 (4)
C16	0.8942 (3)	0.69110 (18)	0.74930 (17)	0.0455 (5)
H16	0.8741	0.6498	0.8325	0.055*
C17	1.0627 (3)	0.76181 (18)	0.68909 (17)	0.0490 (5)
H17	1.1553	0.7678	0.7320	0.059*
C18	1.0963 (2)	0.82417 (17)	0.56554 (17)	0.0437 (5)
C19	0.9568 (3)	0.81699 (17)	0.50216 (17)	0.0452 (5)
H19	0.9768	0.8600	0.4192	0.054*
C20	0.7868 (3)	0.74526 (17)	0.56307 (16)	0.0429 (4)
H20	0.6936	0.7404	0.5201	0.051*
C21	1.3193 (3)	0.9516 (2)	0.39001 (19)	0.0655 (6)
H21A	1.3223	0.8877	0.3534	0.098*
H21B	1.4440	0.9940	0.3686	0.098*
H21C	1.2248	1.0151	0.3623	0.098*
N1	0.22050 (19)	0.46471 (13)	0.88333 (13)	0.0391 (4)
H1	0.1144	0.4213	0.9209	0.047*
N2	0.3060 (2)	0.33757 (15)	0.75584 (14)	0.0446 (4)
N3	0.4599 (2)	0.33551 (16)	0.66572 (14)	0.0510 (4)
N4	0.5383 (3)	0.8162 (2)	0.9136 (2)	0.0929 (8)
O1	0.17078 (18)	0.59323 (13)	0.99468 (12)	0.0513 (4)
O2	1.27013 (19)	0.88929 (14)	0.51707 (13)	0.0605 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0338 (9)	0.0395 (10)	0.0403 (10)	−0.0069 (8)	0.0009 (8)	−0.0136 (8)
C2	0.0333 (9)	0.0393 (10)	0.0432 (10)	−0.0072 (8)	−0.0002 (8)	−0.0141 (8)
C3	0.0308 (9)	0.0356 (9)	0.0413 (10)	−0.0025 (7)	−0.0011 (8)	−0.0091 (8)
C4	0.0307 (9)	0.0399 (10)	0.0413 (10)	−0.0024 (7)	0.0026 (7)	−0.0131 (8)
C5	0.0343 (9)	0.0380 (10)	0.0401 (10)	−0.0019 (7)	0.0001 (8)	−0.0148 (8)
C6	0.0369 (10)	0.0442 (11)	0.0488 (11)	−0.0016 (8)	0.0053 (8)	−0.0173 (9)
C7	0.0392 (11)	0.0556 (13)	0.0624 (13)	−0.0165 (9)	0.0130 (9)	−0.0272 (11)
C8	0.0484 (12)	0.0595 (13)	0.0603 (13)	−0.0036 (10)	0.0143 (10)	−0.0260 (11)
C9	0.0490 (11)	0.0476 (11)	0.0413 (11)	−0.0137 (9)	0.0009 (9)	−0.0200 (9)
C10	0.0488 (12)	0.0673 (14)	0.0520 (12)	−0.0157 (10)	−0.0024 (9)	−0.0273 (11)
C11	0.0568 (14)	0.108 (2)	0.0591 (14)	−0.0353 (14)	0.0017 (11)	−0.0365 (15)
C12	0.105 (2)	0.095 (2)	0.0552 (15)	−0.0659 (18)	0.0019 (14)	−0.0253 (14)
C13	0.117 (2)	0.0580 (15)	0.0675 (16)	−0.0362 (15)	−0.0015 (15)	−0.0248 (13)
C14	0.0752 (15)	0.0500 (13)	0.0617 (14)	−0.0137 (11)	0.0039 (11)	−0.0269 (11)
C15	0.0301 (9)	0.0368 (10)	0.0430 (10)	−0.0029 (7)	0.0023 (8)	−0.0117 (8)
C16	0.0358 (10)	0.0496 (11)	0.0407 (10)	−0.0060 (8)	−0.0007 (8)	−0.0070 (9)
C17	0.0346 (10)	0.0534 (12)	0.0508 (12)	−0.0058 (9)	−0.0056 (9)	−0.0101 (10)
C18	0.0339 (10)	0.0387 (10)	0.0512 (12)	−0.0066 (8)	0.0069 (8)	−0.0144 (9)
C19	0.0470 (11)	0.0420 (10)	0.0377 (10)	−0.0051 (8)	0.0063 (8)	−0.0105 (8)
C20	0.0390 (10)	0.0443 (10)	0.0434 (11)	−0.0039 (8)	−0.0023 (8)	−0.0158 (9)
C21	0.0598 (14)	0.0550 (13)	0.0643 (15)	−0.0165 (10)	0.0248 (11)	−0.0179 (11)
N1	0.0316 (8)	0.0390 (8)	0.0424 (8)	−0.0108 (6)	0.0065 (6)	−0.0151 (7)
N2	0.0395 (8)	0.0440 (9)	0.0488 (9)	−0.0099 (7)	0.0068 (7)	−0.0215 (7)
N3	0.0469 (9)	0.0504 (10)	0.0520 (10)	−0.0053 (8)	0.0107 (8)	−0.0238 (8)
N4	0.0738 (14)	0.0961 (17)	0.1204 (19)	−0.0448 (12)	0.0337 (13)	−0.0735 (16)
O1	0.0405 (7)	0.0616 (9)	0.0534 (8)	−0.0166 (6)	0.0137 (6)	−0.0320 (7)
O2	0.0430 (8)	0.0640 (9)	0.0589 (9)	−0.0189 (7)	0.0111 (7)	−0.0125 (7)

C1—O1	1.236 (2)	C11—H11	0.9300
C1—N1	1.377 (2)	C12—C13	1.381 (4)
C1—C2	1.452 (2)	C12—H12	0.9300
C2—C3	1.388 (2)	C13—C14	1.376 (3)
C2—C7	1.429 (3)	C13—H13	0.9300
C3—C4	1.417 (2)	C14—H14	0.9300
C3—C15	1.484 (2)	C15—C20	1.391 (2)
C4—C5	1.398 (2)	C15—C16	1.392 (2)
C4—C6	1.433 (2)	C16—C17	1.375 (2)
C5—N2	1.343 (2)	C16—H16	0.9300
C5—N1	1.361 (2)	C17—C18	1.382 (3)
C6—N3	1.313 (2)	C17—H17	0.9300
C6—C8	1.496 (2)	C18—O2	1.364 (2)
C7—N4	1.139 (2)	C18—C19	1.384 (3)
C8—H8A	0.9600	C19—C20	1.389 (2)
C8—H8B	0.9600	C19—H19	0.9300
C8—H8C	0.9600	C20—H20	0.9300
C9—C10	1.379 (3)	C21—O2	1.421 (2)
C9—C14	1.383 (3)	C21—H21A	0.9600
C9—N2	1.427 (2)	C21—H21B	0.9600
C10—C11	1.383 (3)	C21—H21C	0.9600
C10—H10	0.9300	N1—H1	0.8600
C11—C12	1.369 (4)	N2—N3	1.394 (2)
O1—C1—N1	120.55 (15)	C14—C13—H13	119.8
O1—C1—C2	123.12 (16)	C12—C13—H13	119.8
N1—C1—C2	116.32 (15)	C13—C14—C9	118.8 (2)
C3—C2—C7	122.01 (15)	C13—C14—H14	120.6
C3—C2—C1	124.02 (16)	C9—C14—H14	120.6
C7—C2—C1	113.84 (15)	C20—C15—C16	118.08 (16)
C2—C3—C4	116.42 (15)	C20—C15—C3	121.91 (16)
C2—C3—C15	120.98 (16)	C16—C15—C3	119.99 (16)
C4—C3—C15	122.60 (15)	C17—C16—C15	120.78 (17)
C5—C4—C3	119.12 (16)	C17—C16—H16	119.6
C5—C4—C6	103.83 (15)	C15—C16—H16	119.6
C3—C4—C6	136.83 (16)	C16—C17—C18	120.81 (18)
N2—C5—N1	127.97 (15)	C16—C17—H17	119.6
N2—C5—C4	108.43 (15)	C18—C17—H17	119.6
N1—C5—C4	123.53 (16)	O2—C18—C17	114.81 (17)
N3—C6—C4	111.18 (15)	O2—C18—C19	125.76 (17)
N3—C6—C8	118.63 (17)	C17—C18—C19	119.43 (16)
C4—C6—C8	130.17 (17)	C18—C19—C20	119.69 (17)
N4—C7—C2	178.0 (2)	C18—C19—H19	120.2
C6—C8—H8A	109.5	C20—C19—H19	120.2
C6—C8—H8B	109.5	C19—C20—C15	121.20 (18)
H8A—C8—H8B	109.5	C19—C20—H20	119.4
C6—C8—H8C	109.5	C15—C20—H20	119.4
H8A—C8—H8C	109.5	O2—C21—H21A	109.5
H8B—C8—H8C	109.5	O2—C21—H21B	109.5
C10—C9—C14	121.36 (18)	H21A—C21—H21B	109.5
C10—C9—N2	120.09 (18)	O2—C21—H21C	109.5
C14—C9—N2	118.54 (18)	H21A—C21—H21C	109.5
C9—C10—C11	118.8 (2)	H21B—C21—H21C	109.5
C9—C10—H10	120.6	C5—N1—C1	120.54 (14)
C11—C10—H10	120.6	C5—N1—H1	119.7
C12—C11—C10	120.4 (2)	C1—N1—H1	119.7
C12—C11—H11	119.8	C5—N2—N3	110.21 (14)
C10—C11—H11	119.8	C5—N2—C9	130.98 (15)
C11—C12—C13	120.2 (2)	N3—N2—C9	118.76 (14)
C11—C12—H12	119.9	C6—N3—N2	106.35 (15)
C13—C12—H12	119.9	C18—O2—C21	118.36 (16)
C14—C13—C12	120.4 (3)
O1—C1—C2—C3	−175.69 (18)	C4—C3—C15—C20	56.1 (2)
N1—C1—C2—C3	2.7 (3)	C2—C3—C15—C16	54.0 (2)
O1—C1—C2—C7	0.3 (3)	C4—C3—C15—C16	−125.4 (2)
N1—C1—C2—C7	178.62 (16)	C20—C15—C16—C17	−1.0 (3)
C7—C2—C3—C4	−178.28 (17)	C3—C15—C16—C17	−179.57 (17)
C1—C2—C3—C4	−2.6 (3)	C15—C16—C17—C18	0.0 (3)
C7—C2—C3—C15	2.3 (3)	C16—C17—C18—O2	−179.12 (17)
C1—C2—C3—C15	177.93 (17)	C16—C17—C18—C19	1.1 (3)
C2—C3—C4—C5	0.8 (2)	O2—C18—C19—C20	179.00 (17)
C15—C3—C4—C5	−179.76 (16)	C17—C18—C19—C20	−1.3 (3)
C2—C3—C4—C6	−172.7 (2)	C18—C19—C20—C15	0.3 (3)
C15—C3—C4—C6	6.7 (3)	C16—C15—C20—C19	0.8 (3)
C3—C4—C5—N2	−176.16 (16)	C3—C15—C20—C19	179.38 (16)
C6—C4—C5—N2	−0.7 (2)	N2—C5—N1—C1	175.58 (17)
C3—C4—C5—N1	0.9 (3)	C4—C5—N1—C1	−0.9 (3)
C6—C4—C5—N1	176.38 (16)	O1—C1—N1—C5	177.60 (16)
C5—C4—C6—N3	0.4 (2)	C2—C1—N1—C5	−0.8 (2)
C3—C4—C6—N3	174.6 (2)	N1—C5—N2—N3	−176.14 (17)
C5—C4—C6—C8	−177.7 (2)	C4—C5—N2—N3	0.8 (2)
C3—C4—C6—C8	−3.5 (4)	N1—C5—N2—C9	1.4 (3)
C3—C2—C7—N4	171 (8)	C4—C5—N2—C9	178.32 (18)
C1—C2—C7—N4	−5(8)	C10—C9—N2—C5	44.7 (3)
C14—C9—C10—C11	0.3 (3)	C14—C9—N2—C5	−136.3 (2)
N2—C9—C10—C11	179.32 (18)	C10—C9—N2—N3	−137.97 (19)
C9—C10—C11—C12	−1.3 (3)	C14—C9—N2—N3	41.1 (3)
C10—C11—C12—C13	1.4 (4)	C4—C6—N3—N2	0.0 (2)
C11—C12—C13—C14	−0.3 (4)	C8—C6—N3—N2	178.40 (17)
C12—C13—C14—C9	−0.7 (4)	C5—N2—N3—C6	−0.5 (2)
C10—C9—C14—C13	0.7 (3)	C9—N2—N3—C6	−178.39 (17)
N2—C9—C14—C13	−178.32 (19)	C17—C18—O2—C21	177.44 (17)
C2—C3—C15—C20	−124.5 (2)	C19—C18—O2—C21	−2.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.06	2.8523 (18)	153.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.06	2.8523 (18)	153

Symmetry code: (i) .