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

Zhang, X.-Y.; Li, X.-Y.; Wang, X.; Li, D.-F.; Fan, X.-S.

doi:10.1107/S1600536808027852

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1888

doi:10.1107/S1600536808027852

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

Xin-Ying Zhang,^a ^* Xiao-Yan Li,^a Xia Wang,^a Dong-Fang Li ^a and Xue-Sen Fan ^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

(Received 22 August 2008; accepted 30 August 2008; online 6 September 2008)

In the title compound, C₂₁H₁₆N₄O₂, the dihedral angle between the methoxy-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, molecules are linked together via intermolecular 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_r = 356.38
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.114
S = 1.02
3136 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) -x, -y+1, -z+2.

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).

Supporting information

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

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

checkCIF report

Comment top

Pyrazolo[3,4-b]pyridine derivatives have been found of interests for their biological and pharmacological activities, such as antiviral (Ludwig et al., 2004). Moreover, pyrazolo[3,4-b]pyridin-6-ones as a subunit of pyrazolo[3,4-b]pyridine acted as potential hypnotic drugs in many cases (Falcó et al., 2005). Due to their importance, many methods have been reported for the construction of pyrazolo[3,4-b]pyridine derivatives including pyrazolo[3,4-b]pyridin-6-ones (Quiroga et al., 1999; Falcó et al., 2005). Herein, we report the crystal structure of the title compound, one of pyrazolo[3,4-b]pyridin-6-one derivatives.

In the title compound there are four rings including two phenyl rings, one pyridinone ring and one pyrazole ring. The pyridinone ring and the pyrazole ring is almost co-planar and formed a ring system. The dihedral angle between this ring system and the methoxy-substituted phenyl ring is 57.4 (1)°, which is probably due to the repulsion of the cyano group on the pyridinone ring and the hydrogen atoms on the ortho-positions of the phenyl ring connected with the pyridinone ring, and the repulsion between these hydrogen atoms and the methyl group on the pyrazole ring. The dihedral angle between the non-substituted phenyl ring and the ring system is 135.6 (1)°.

In the crystal structure the molecules are connected via intermolecular N—H···O hydrogen bonding (Table 1).

Related literature top

For 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 top

To 1 ml of 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF₄]) were added 4-methoxybenzaldehyde (1 mmol, II) and ethyl cyanoacetate (1 mmol). The mixture was stirred at 80 °C until the disappearance of II. Then, 5-amino-3-methyl-1-phenylpyrazole (1 mmol) and FeCl₃.6H₂O (0.2 mmol) was added and the mixture was continued to be stirred at the same temperature to complete the reaction (monitored by TLC). The reaction time was 10 h totally. Upon completion, the mixture was cooled to room temperature and 2 ml of 50% ethanol in water was added. The product was collected by suction and rinsed with water and cool ethanol in a yield of 90% as white solid. Single crystals of the title compound were obtained by slow evaporation of the solvent from an ethyl acetate-ethanol (1:1 v/v) solution.

Computing details top

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).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal Structure of the title compound with view along the a axis. Intermolecular N—H···O hydrogen bonding is shown as dashed lines.

6,7-Dihydro-4-(4-methoxyphenyl)-3-methyl-6-oxo-1-phenyl-1H- pyrazolo[3,4-b]pyridine-5-carbonitrile top

Crystal data top

C₂₁H₁₆N₄O₂	Z = 2
M_r = 356.38	F(000) = 372
Triclinic, P1	D_x = 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

Data collection top

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

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) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0514P)² + 0.1601P] where P = (F_o² + 2F_c²)/3
3136 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₁H₁₆N₄O₂	γ = 87.471 (2)°
M_r = 356.38	V = 865.2 (2) Å³
Triclinic, P1	Z = 2
a = 7.0621 (11) Å	Mo Kα radiation
b = 11.0272 (17) Å	µ = 0.09 mm⁻¹
c = 12.1743 (19) Å	T = 295 K
α = 68.467 (2)°	0.43 × 0.30 × 0.11 mm
β = 78.949 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2236 reflections with I > 2σ(I)
6198 measured reflections	R_int = 0.019
3136 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	Δρ_max = 0.15 e Å⁻³
3136 reflections	Δρ_min = −0.21 e Å⁻³
246 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	0.2756 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆N₄O₂
M_r	356.38
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.0621 (11), 11.0272 (17), 12.1743 (19)
α, β, γ (°)	68.467 (2), 78.949 (2), 87.471 (2)
V (Å³)	865.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.30 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6198, 3136, 2236
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.114, 1.02
No. of reflections	3136
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.06	2.8523 (18)	152.5

Symmetry code: (i) −x, −y+1, −z+2.

Acknowledgements

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

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Falcó, J. L., Lloveras, M., Buira, I., Teixidó, J., Borrell, J. I., Méndez, E., Terencio, J., Palomer, A. & Guglietta, A. (2005). Eur. J. Med. Chem. 40, 1179–1187. Web of Science PubMed Google Scholar
Ludwig, S., Planz, O., Sedlacek, H. H. & Pleschka, S. (2004). PCT Int. Appl. WO 2 004 085 682. 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 10| October 2008| Page o1888

doi:10.1107/S1600536808027852

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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