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

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5-(Pyridin-4-ylmeth­yl)-1H-pyrazolo­[3,4-d]pyrimidin-4(5H)-one

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and bLaboratoires de Diffraction des Rayons X, Centre National pour la Recherche, Scientifique et Technique, Rabat, Morocco
*Correspondence e-mail: abdalsalam_1977@hotmail.com

(Received 17 June 2011; accepted 25 June 2011; online 6 July 2011)

In the title compound, C11H9N5O, the pyrazolo­pyrimidin-4-one ring system is almost planar, with a maximum deviation of 0.0546 (13) Å for the O atom. The crystal packing is stabilized by inter­molecular N—H⋯N, C—H⋯O and C—H⋯N hydrogen bonds. In addition, ππ stacking is found between the pyridine ring and the pyrazolo­pyrimidin-4-one ring systems, with centroid–centroid distances in the range 3.9627 (12)–4.6781 (12) Å.

Related literature

For a related structure, see: Al Subari et al. (2010[Al Subari, A., Bouhfid, R., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o454.]). For the biological activity of pyrazolo­pyrimidinone derivatives, see: Kim et al. (2001[Kim, D. K., Ryu, D. H., Lee, N., Lee, J. Y., Kim, J. S., Lee, S., Choi, J. Y., Ru, J. H., Kim, N. H., Im, G. J., Choi, W. S. & Kim, T. K. (2001). Bioorg. Med. Chem. 9, 1895-1899.]); Ali et al. (2009[Ali, T. E. S. (2009). Eur. J. Med. Chem. 44, 4385-4392.]).

[Scheme 1]

Experimental

Crystal data
  • C11H9N5O

  • Mr = 227.23

  • Monoclinic, P 21

  • a = 4.6371 (3) Å

  • b = 19.2731 (10) Å

  • c = 5.8593 (3) Å

  • β = 102.498 (2)°

  • V = 511.24 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.25 × 0.22 × 0.17 mm

Data collection
  • Bruker APEXII CCD detector diffractometer

  • 6285 measured reflections

  • 2603 independent reflections

  • 2201 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.085

  • S = 1.05

  • 2603 reflections

  • 158 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3N⋯N5i 0.90 (2) 1.96 (2) 2.840 (2) 168 (2)
C4—H4⋯N4ii 0.93 2.61 3.526 (2) 167
C9—H9⋯N2iii 0.93 2.36 3.289 (2) 174
C11—H11⋯O1iv 0.93 2.52 3.430 (2) 167
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+1]; (ii) [-x+1, y-{\script{1\over 2}}, -z]; (iii) x-1, y, z-1; (iv) x+1, y, z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Pyrazolopyrimidinone derivatives have attracted the attention of numerous researchers over many years due to their important biological activities [Kim, et al. 2001 and Ali, et al. 2009].

In the title compound, C11H9N5O, the 4H-pyrazolo[3,4-d]pyrimidin-4-one core is almost planar (maximum atomic deviation = 0.0546 (13) Å for the oxygen atom of the system) and makes a dihedral angle of 73.94 (7)° with the attached pyridin ring (maximum atomic deviation = 0.041 (18) Å of the nitrogen atom of the ring). The crystal packing is stabilized by N—H···O and C—H···N intermolecular H-bonds and ππ stacking between pyridin and pyrazolo ring systems [Cg to Cg distances = 4.6781 (12) Å to 3.9627 (12) Å].

Related literature top

For a related structure, see: Al Subari et al. (2010). For the biological activity of pyrazolopyrimidinone derivatives, see: Kim et al. (2001); Ali et al. (2009).

Experimental top

allopurinol (1 g, 7.4 mmol), 4-chloromethylpyridine (1.8 g, 14.7 mmol) and potassium carbonate (1.5 g, 11.2 mmol) with amount of catalytic tetra-n-butylammonium bromide were stirred in DMF (30 ml) for 72 h. The solid material was removed by filtration and the solvent evaporated under vacuum. Dichloromethane (20 ml) was added and the solution filtered. The solid product was purified by recrystallization from ethanol to afford white crystals in 60% yield.

Refinement top

The H atoms bound to C were treated as riding with their parent atoms [C—H distances are 0.93Å for CH groups with Uiso(H) = 1.2 Ueq(C), and 0.97 Å for CH3 groups with Uiso(H) = 1.5 Ueq(C). The nitrogen-bound H atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.88 (2).

The title compound crystallizes in the non centrosymmetric space group P21 and as the absolute configuration is not determined from the measured data, the Friedel equivalent reflections are merged before refinement with XPREP software.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular view of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Partial packing view showing the chain formed by N—H···O and C—H···N hydrogen bondings. H atoms not involved in hydrogen bonds have been omitted for clarity.
5-(Pyridin-4-ylmethyl)-1H-pyrazolo[3,4-d]pyrimidin- 4(5H)-one top
Crystal data top
C11H9N5OF(000) = 236
Mr = 227.23Dx = 1.476 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 342 reflections
a = 4.6371 (3) Åθ = 2.4–25.6°
b = 19.2731 (10) ŵ = 0.10 mm1
c = 5.8593 (3) ÅT = 296 K
β = 102.498 (2)°Prism, colourless
V = 511.24 (5) Å30.25 × 0.22 × 0.17 mm
Z = 2
Data collection top
Bruker APEXII CCD detector
diffractometer
2201 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 28.9°, θmin = 2.1°
ω and ϕ scansh = 66
6285 measured reflectionsk = 2626
2603 independent reflectionsl = 77
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0427P)2 + 0.0014P]
where P = (Fo2 + 2Fc2)/3
2603 reflections(Δ/σ)max = 0.001
158 parametersΔρmax = 0.16 e Å3
2 restraintsΔρmin = 0.22 e Å3
Crystal data top
C11H9N5OV = 511.24 (5) Å3
Mr = 227.23Z = 2
Monoclinic, P21Mo Kα radiation
a = 4.6371 (3) ŵ = 0.10 mm1
b = 19.2731 (10) ÅT = 296 K
c = 5.8593 (3) Å0.25 × 0.22 × 0.17 mm
β = 102.498 (2)°
Data collection top
Bruker APEXII CCD detector
diffractometer
2201 reflections with I > 2σ(I)
6285 measured reflectionsRint = 0.030
2603 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0362 restraints
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.16 e Å3
2603 reflectionsΔρmin = 0.22 e Å3
158 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
xyzUiso*/Ueq
N20.7680 (3)1.03978 (7)0.5859 (2)0.0280 (3)
N10.3899 (3)0.95388 (6)0.5329 (2)0.0242 (3)
N30.7129 (3)1.11511 (7)0.2529 (2)0.0275 (3)
N50.8324 (3)0.71619 (7)0.6387 (3)0.0326 (3)
N40.5292 (3)1.12382 (7)0.0394 (2)0.0312 (3)
O10.0403 (3)0.93783 (6)0.1944 (2)0.0343 (3)
C80.3807 (3)1.03227 (8)0.2246 (3)0.0233 (3)
C110.6365 (3)0.98760 (8)0.6577 (3)0.0257 (3)
H110.71550.97130.80750.031*
C100.6293 (3)1.06125 (8)0.3675 (3)0.0235 (3)
C70.2488 (4)0.97246 (8)0.3022 (3)0.0242 (3)
C10.4678 (3)0.83113 (8)0.6455 (3)0.0250 (3)
C60.2764 (4)0.89454 (8)0.6453 (3)0.0289 (4)
H6A0.07640.88420.56260.035*
H6B0.27080.90660.80500.035*
C20.6726 (4)0.81124 (9)0.8437 (3)0.0298 (4)
H20.69260.83600.98250.036*
C50.4487 (4)0.79196 (8)0.4448 (3)0.0322 (4)
H50.31300.80360.30870.039*
C40.6333 (4)0.73540 (8)0.4486 (3)0.0351 (4)
H40.61810.70950.31250.042*
C90.3281 (4)1.07419 (8)0.0210 (3)0.0286 (3)
H90.17351.06770.10780.034*
C30.8469 (4)0.75365 (9)0.8304 (3)0.0332 (4)
H30.98270.74040.96460.040*
H3N0.869 (4)1.1429 (12)0.304 (4)0.060 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0245 (7)0.0290 (7)0.0283 (7)0.0012 (6)0.0011 (6)0.0026 (6)
N10.0251 (6)0.0209 (6)0.0264 (7)0.0009 (5)0.0052 (5)0.0002 (5)
N30.0274 (7)0.0252 (7)0.0290 (8)0.0025 (6)0.0042 (6)0.0006 (6)
N50.0329 (8)0.0251 (7)0.0411 (9)0.0029 (6)0.0108 (7)0.0017 (6)
N40.0343 (8)0.0293 (7)0.0288 (8)0.0020 (6)0.0045 (6)0.0010 (6)
O10.0323 (6)0.0308 (6)0.0355 (7)0.0077 (5)0.0025 (5)0.0025 (5)
C80.0213 (7)0.0222 (7)0.0252 (8)0.0027 (6)0.0020 (6)0.0028 (6)
C110.0259 (8)0.0267 (8)0.0222 (8)0.0053 (6)0.0003 (6)0.0015 (6)
C100.0227 (7)0.0215 (7)0.0263 (8)0.0017 (6)0.0050 (6)0.0034 (6)
C70.0225 (7)0.0223 (7)0.0268 (8)0.0032 (6)0.0032 (6)0.0039 (6)
C10.0264 (8)0.0221 (7)0.0280 (8)0.0036 (6)0.0096 (7)0.0014 (6)
C60.0298 (9)0.0261 (8)0.0334 (10)0.0017 (7)0.0130 (8)0.0010 (6)
C20.0357 (9)0.0269 (8)0.0256 (8)0.0006 (7)0.0041 (7)0.0001 (6)
C50.0360 (10)0.0319 (9)0.0264 (9)0.0023 (7)0.0019 (7)0.0006 (7)
C40.0448 (11)0.0282 (9)0.0337 (10)0.0017 (8)0.0114 (9)0.0033 (7)
C90.0296 (8)0.0289 (8)0.0252 (8)0.0009 (7)0.0015 (7)0.0023 (6)
C30.0317 (9)0.0289 (8)0.0360 (11)0.0002 (7)0.0006 (8)0.0058 (7)
Geometric parameters (Å, º) top
N2—C111.293 (2)C8—C71.425 (2)
N2—C101.366 (2)C11—H110.9300
N1—C111.379 (2)C1—C51.384 (2)
N1—C71.415 (2)C1—C21.386 (2)
N1—C61.4725 (19)C1—C61.510 (2)
N3—C101.339 (2)C6—H6A0.9700
N3—N41.363 (2)C6—H6B0.9700
N3—H3N0.897 (16)C2—C31.385 (3)
N5—C31.325 (2)C2—H20.9300
N5—C41.336 (2)C5—C41.383 (2)
N4—C91.324 (2)C5—H50.9300
O1—C71.231 (2)C4—H40.9300
C8—C101.387 (2)C9—H90.9300
C8—C91.418 (2)C3—H30.9300
C11—N2—C10112.37 (14)C2—C1—C6121.35 (15)
C11—N1—C7123.10 (13)N1—C6—C1111.23 (11)
C11—N1—C6117.67 (14)N1—C6—H6A109.4
C7—N1—C6119.20 (13)C1—C6—H6A109.4
C10—N3—N4111.39 (14)N1—C6—H6B109.4
C10—N3—H3N126.6 (15)C1—C6—H6B109.4
N4—N3—H3N122.0 (15)H6A—C6—H6B108.0
C3—N5—C4117.08 (15)C3—C2—C1118.49 (16)
C9—N4—N3105.96 (13)C3—C2—H2120.8
C10—C8—C9104.34 (14)C1—C2—H2120.8
C10—C8—C7119.42 (14)C4—C5—C1119.39 (16)
C9—C8—C7136.22 (15)C4—C5—H5120.3
N2—C11—N1126.12 (15)C1—C5—H5120.3
N2—C11—H11116.9N5—C4—C5123.05 (16)
N1—C11—H11116.9N5—C4—H4118.5
N3—C10—N2125.17 (14)C5—C4—H4118.5
N3—C10—C8107.61 (13)N4—C9—C8110.70 (15)
N2—C10—C8127.23 (14)N4—C9—H9124.7
O1—C7—N1120.18 (14)C8—C9—H9124.7
O1—C7—C8128.22 (16)N5—C3—C2124.12 (17)
N1—C7—C8111.59 (14)N5—C3—H3117.9
C5—C1—C2117.87 (15)C2—C3—H3117.9
C5—C1—C6120.77 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···N5i0.90 (2)1.96 (2)2.840 (2)168 (2)
C4—H4···N4ii0.932.613.526 (2)167
C9—H9···N2iii0.932.363.289 (2)174
C11—H11···O1iv0.932.523.430 (2)167
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x+1, y1/2, z; (iii) x1, y, z1; (iv) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC11H9N5O
Mr227.23
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)4.6371 (3), 19.2731 (10), 5.8593 (3)
β (°) 102.498 (2)
V3)511.24 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.25 × 0.22 × 0.17
Data collection
DiffractometerBruker APEXII CCD detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6285, 2603, 2201
Rint0.030
(sin θ/λ)max1)0.680
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.085, 1.05
No. of reflections2603
No. of parameters158
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.22

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···N5i0.90 (2)1.96 (2)2.840 (2)168 (2)
C4—H4···N4ii0.932.613.526 (2)167
C9—H9···N2iii0.932.363.289 (2)174
C11—H11···O1iv0.932.523.430 (2)167
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x+1, y1/2, z; (iii) x1, y, z1; (iv) x+1, y, z+1.
 

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UA TRS, CNRST) for the X-ray measurements.

References

First citationAli, T. E. S. (2009). Eur. J. Med. Chem. 44, 4385–4392.  Web of Science CrossRef PubMed Google Scholar
First citationAl Subari, A., Bouhfid, R., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o454.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKim, D. K., Ryu, D. H., Lee, N., Lee, J. Y., Kim, J. S., Lee, S., Choi, J. Y., Ru, J. H., Kim, N. H., Im, G. J., Choi, W. S. & Kim, T. K. (2001). Bioorg. Med. Chem. 9, 1895–1899.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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