organic compounds
H-spiro[pyrazolo[3,4-d]pyrimidine-4,2′-[1,3,4]thiadiazole]
of 1,5-diethyl-3′,5′-diphenyl-1,5-dihydro-3′aLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, bLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, University Mohammed V, Rabat, Morocco, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: em_essassi@yahoo.fr
In the title compound, C22H22N6S, the pyrazolo[3,4-d]pyrimidine rings system is almost planar, with the r.m.s. deviation for the fitted atoms being 0.011 Å. The two phenyl groups linked to the thiadiazole ring are nearly perpendicular to the fused-ring system as indicated by the dihedral angles of 86.93 (10) and 83.35 (11)°. However, the phenyl rings are almost coplanar with the thiadiazole ring (r.m.s. deviation = 0.015 Å), forming dihedral angles of 10.44 (11) and 10.06 (12)°. In the crystal, molecules are connected into a supramolecular layer in the ac plane via C—H⋯π interactions.
Keywords: crystal structure; pyrazolo[3,4-d]pyrimidine; thiadiazole.
CCDC reference: 1425539
1. Related literature
For biological properties of pyrazolo[3,4-d]pyrimidine derivatives, see: Chern et al. (2004); Schenone et al. (2009); Dinér et al. (2012); Taliani et al. (2010); Trivedi et al. (2012). For related structures, see: El Fal et al. (2014, 2015); Ahoya et al. (2011); Anothane et al. (2012).
2. Experimental
2.1. Crystal data
|
2.3. Refinement
|
Data collection: APEX2 (Bruker, 2009); cell SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2013.
Supporting information
CCDC reference: 1425539
10.1107/S2056989015017405/tk5387sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015017405/tk5387Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015017405/tk5387Isup3.cml
To a solution of 1,5-diethyl-1H-pyrazolo [3,4-d] pyrimidin-4(5H)–thione (2.08 g, 10 mmol) and diphenyl hydrazonoyl chloride (3.00 g, 13 mmol) in THF (30 ml) was added triethylamine (2 ml). The mixture was refluxed for 24 h. The precipitate was collected by filtration and was separated by silica gel
(hexane/ethyl acetate: 8/2). The solid obtained was recrystallized from ethanol to afford the title compound as yellow crystals (yield: 60%; m.p. = 468 K).The H atoms were located in a difference map and treated as riding with C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene) and C—H = 0.96 Å (methyl). All hydrogen with Uiso(H) = 1.2 Ueq(aromatic and methylene) and Uiso(H) = 1.5 Ueq(methyl). The reflection (0 2 0) was affected by beamstop and was removed from the refinement.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXL2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles. |
C22H22N6S | Dx = 1.292 Mg m−3 |
Mr = 402.51 | Melting point: 468 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 14.501 (5) Å | Cell parameters from 4224 reflections |
b = 22.898 (5) Å | θ = 2.3–26.4° |
c = 12.468 (4) Å | µ = 0.18 mm−1 |
V = 4140 (2) Å3 | T = 296 K |
Z = 8 | Block, yellow |
F(000) = 1696 | 0.37 × 0.34 × 0.29 mm |
Bruker X8 APEX diffractometer | 4224 independent reflections |
Radiation source: fine-focus sealed tube | 2566 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.079 |
φ and ω scans | θmax = 26.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −18→17 |
Tmin = 0.589, Tmax = 0.746 | k = −24→28 |
25025 measured reflections | l = −15→15 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.0625P)2 + 0.732P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
4224 reflections | Δρmax = 0.31 e Å−3 |
262 parameters | Δρmin = −0.30 e Å−3 |
C22H22N6S | V = 4140 (2) Å3 |
Mr = 402.51 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 14.501 (5) Å | µ = 0.18 mm−1 |
b = 22.898 (5) Å | T = 296 K |
c = 12.468 (4) Å | 0.37 × 0.34 × 0.29 mm |
Bruker X8 APEX diffractometer | 4224 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2566 reflections with I > 2σ(I) |
Tmin = 0.589, Tmax = 0.746 | Rint = 0.079 |
25025 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.31 e Å−3 |
4224 reflections | Δρmin = −0.30 e Å−3 |
262 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.48041 (15) | 0.16398 (10) | 0.52664 (19) | 0.0383 (5) | |
C2 | 0.54607 (15) | 0.07863 (9) | 0.63901 (19) | 0.0363 (5) | |
C3 | 0.49773 (15) | 0.04386 (10) | 0.72025 (19) | 0.0373 (5) | |
C4 | 0.41299 (17) | 0.04978 (11) | 0.7732 (2) | 0.0511 (7) | |
H4 | 0.3727 | 0.0809 | 0.7631 | 0.061* | |
C5 | 0.53365 (15) | −0.00752 (10) | 0.75801 (19) | 0.0377 (5) | |
C6 | 0.65913 (16) | −0.00200 (10) | 0.6605 (2) | 0.0413 (6) | |
H6 | 0.7162 | −0.0164 | 0.6392 | 0.050* | |
C7 | 0.69620 (18) | 0.07699 (12) | 0.5361 (2) | 0.0554 (7) | |
H7A | 0.7560 | 0.0814 | 0.5700 | 0.066* | |
H7B | 0.6733 | 0.1158 | 0.5199 | 0.066* | |
C8 | 0.7081 (3) | 0.04447 (17) | 0.4342 (3) | 0.1022 (13) | |
H8A | 0.7498 | 0.0654 | 0.3884 | 0.153* | |
H8B | 0.6495 | 0.0406 | 0.3992 | 0.153* | |
H8C | 0.7327 | 0.0064 | 0.4492 | 0.153* | |
C9 | 0.4750 (2) | −0.08616 (13) | 0.8837 (3) | 0.0726 (9) | |
H9A | 0.4554 | −0.0814 | 0.9576 | 0.087* | |
H9B | 0.5377 | −0.1009 | 0.8841 | 0.087* | |
C10 | 0.4139 (3) | −0.12911 (14) | 0.8295 (3) | 0.0962 (13) | |
H10A | 0.4166 | −0.1657 | 0.8668 | 0.144* | |
H10B | 0.4340 | −0.1345 | 0.7568 | 0.144* | |
H10C | 0.3517 | −0.1148 | 0.8298 | 0.144* | |
C11 | 0.61067 (15) | 0.15818 (10) | 0.76316 (19) | 0.0383 (6) | |
C12 | 0.66082 (17) | 0.11905 (11) | 0.8257 (2) | 0.0478 (6) | |
H12 | 0.6632 | 0.0797 | 0.8072 | 0.057* | |
C13 | 0.70698 (17) | 0.13906 (13) | 0.9156 (2) | 0.0538 (7) | |
H13 | 0.7404 | 0.1128 | 0.9571 | 0.065* | |
C14 | 0.70444 (18) | 0.19696 (13) | 0.9449 (2) | 0.0576 (8) | |
H14 | 0.7357 | 0.2099 | 1.0054 | 0.069* | |
C15 | 0.65481 (18) | 0.23514 (13) | 0.8829 (2) | 0.0577 (8) | |
H15 | 0.6524 | 0.2744 | 0.9021 | 0.069* | |
C16 | 0.60827 (16) | 0.21655 (11) | 0.7924 (2) | 0.0479 (7) | |
H16 | 0.5753 | 0.2432 | 0.7512 | 0.058* | |
C17 | 0.43453 (15) | 0.20319 (10) | 0.4501 (2) | 0.0399 (6) | |
C18 | 0.39468 (17) | 0.18210 (12) | 0.3574 (2) | 0.0505 (7) | |
H18 | 0.3970 | 0.1423 | 0.3424 | 0.061* | |
C19 | 0.35137 (19) | 0.21958 (14) | 0.2866 (2) | 0.0623 (8) | |
H19 | 0.3252 | 0.2051 | 0.2239 | 0.075* | |
C20 | 0.3471 (2) | 0.27838 (14) | 0.3090 (3) | 0.0665 (9) | |
H20 | 0.3182 | 0.3037 | 0.2614 | 0.080* | |
C21 | 0.38543 (19) | 0.29943 (13) | 0.4014 (3) | 0.0646 (8) | |
H21 | 0.3823 | 0.3392 | 0.4165 | 0.077* | |
C22 | 0.42870 (18) | 0.26235 (11) | 0.4724 (2) | 0.0527 (7) | |
H22 | 0.4540 | 0.2771 | 0.5354 | 0.063* | |
N1 | 0.52713 (13) | 0.18375 (8) | 0.60593 (16) | 0.0414 (5) | |
N2 | 0.56296 (14) | 0.14038 (8) | 0.67014 (16) | 0.0444 (5) | |
N3 | 0.63253 (12) | 0.04874 (8) | 0.61271 (16) | 0.0396 (5) | |
N4 | 0.61620 (13) | −0.03289 (9) | 0.73112 (17) | 0.0430 (5) | |
N5 | 0.47290 (14) | −0.02945 (9) | 0.82976 (18) | 0.0523 (6) | |
N6 | 0.39730 (15) | 0.00565 (10) | 0.8391 (2) | 0.0618 (7) | |
S1 | 0.47272 (5) | 0.08793 (3) | 0.51716 (6) | 0.0486 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0362 (12) | 0.0355 (13) | 0.0431 (14) | 0.0013 (10) | −0.0001 (11) | 0.0032 (11) |
C2 | 0.0380 (12) | 0.0283 (12) | 0.0425 (14) | 0.0008 (10) | −0.0069 (10) | −0.0008 (10) |
C3 | 0.0362 (12) | 0.0305 (12) | 0.0453 (15) | 0.0006 (10) | −0.0020 (10) | −0.0003 (11) |
C4 | 0.0440 (14) | 0.0471 (16) | 0.0621 (19) | 0.0096 (12) | 0.0070 (12) | 0.0006 (14) |
C5 | 0.0365 (12) | 0.0331 (13) | 0.0435 (14) | −0.0019 (10) | −0.0020 (10) | 0.0033 (11) |
C6 | 0.0332 (12) | 0.0411 (14) | 0.0496 (15) | 0.0055 (11) | −0.0048 (11) | −0.0022 (12) |
C7 | 0.0491 (15) | 0.0602 (18) | 0.0568 (19) | −0.0083 (13) | 0.0078 (12) | 0.0152 (15) |
C8 | 0.127 (3) | 0.107 (3) | 0.073 (3) | −0.015 (2) | 0.048 (2) | −0.004 (2) |
C9 | 0.070 (2) | 0.066 (2) | 0.082 (2) | 0.0031 (17) | 0.0156 (17) | 0.0367 (18) |
C10 | 0.118 (3) | 0.054 (2) | 0.117 (3) | −0.008 (2) | 0.038 (3) | 0.014 (2) |
C11 | 0.0373 (12) | 0.0403 (14) | 0.0372 (14) | −0.0053 (10) | 0.0004 (10) | −0.0034 (11) |
C12 | 0.0557 (15) | 0.0409 (15) | 0.0469 (16) | −0.0021 (13) | −0.0091 (12) | 0.0008 (12) |
C13 | 0.0506 (15) | 0.068 (2) | 0.0425 (16) | −0.0036 (14) | −0.0098 (12) | 0.0037 (14) |
C14 | 0.0461 (15) | 0.075 (2) | 0.0516 (18) | −0.0088 (15) | −0.0046 (12) | −0.0178 (15) |
C15 | 0.0515 (15) | 0.0553 (18) | 0.066 (2) | −0.0024 (14) | −0.0024 (14) | −0.0238 (15) |
C16 | 0.0451 (14) | 0.0396 (15) | 0.0591 (18) | 0.0003 (11) | −0.0071 (12) | −0.0098 (13) |
C17 | 0.0360 (12) | 0.0388 (14) | 0.0449 (15) | 0.0055 (11) | 0.0022 (10) | 0.0085 (11) |
C18 | 0.0537 (15) | 0.0487 (16) | 0.0491 (17) | 0.0087 (13) | −0.0019 (13) | 0.0070 (13) |
C19 | 0.0596 (17) | 0.074 (2) | 0.0532 (19) | 0.0092 (15) | −0.0122 (14) | 0.0101 (16) |
C20 | 0.0640 (18) | 0.061 (2) | 0.074 (2) | 0.0148 (16) | −0.0108 (16) | 0.0262 (17) |
C21 | 0.0640 (18) | 0.0450 (17) | 0.085 (2) | 0.0131 (14) | −0.0074 (17) | 0.0128 (16) |
C22 | 0.0547 (15) | 0.0406 (16) | 0.0627 (19) | 0.0054 (13) | −0.0086 (13) | 0.0080 (13) |
N1 | 0.0478 (11) | 0.0308 (11) | 0.0457 (12) | 0.0023 (9) | −0.0042 (10) | 0.0065 (9) |
N2 | 0.0595 (13) | 0.0278 (11) | 0.0461 (13) | −0.0011 (9) | −0.0168 (10) | 0.0046 (9) |
N3 | 0.0373 (10) | 0.0369 (11) | 0.0446 (12) | −0.0005 (9) | 0.0006 (8) | 0.0041 (9) |
N4 | 0.0377 (11) | 0.0395 (12) | 0.0519 (14) | 0.0061 (9) | −0.0012 (9) | 0.0091 (10) |
N5 | 0.0481 (12) | 0.0468 (13) | 0.0619 (15) | 0.0026 (10) | 0.0098 (11) | 0.0169 (11) |
N6 | 0.0516 (13) | 0.0624 (16) | 0.0714 (17) | 0.0052 (12) | 0.0180 (12) | 0.0111 (13) |
S1 | 0.0567 (4) | 0.0362 (4) | 0.0531 (4) | −0.0001 (3) | −0.0217 (3) | 0.0025 (3) |
C1—N1 | 1.281 (3) | C10—H10B | 0.9600 |
C1—C17 | 1.469 (3) | C10—H10C | 0.9600 |
C1—S1 | 1.749 (2) | C11—C16 | 1.386 (3) |
C2—N3 | 1.466 (3) | C11—C12 | 1.393 (3) |
C2—C3 | 1.467 (3) | C11—N2 | 1.411 (3) |
C2—N2 | 1.487 (3) | C12—C13 | 1.383 (3) |
C2—S1 | 1.867 (2) | C12—H12 | 0.9300 |
C3—C5 | 1.370 (3) | C13—C14 | 1.376 (4) |
C3—C4 | 1.401 (3) | C13—H13 | 0.9300 |
C4—N6 | 1.323 (3) | C14—C15 | 1.371 (4) |
C4—H4 | 0.9300 | C14—H14 | 0.9300 |
C5—N5 | 1.352 (3) | C15—C16 | 1.381 (4) |
C5—N4 | 1.372 (3) | C15—H15 | 0.9300 |
C6—N4 | 1.290 (3) | C16—H16 | 0.9300 |
C6—N3 | 1.361 (3) | C17—C18 | 1.379 (4) |
C6—H6 | 0.9300 | C17—C22 | 1.386 (3) |
C7—N3 | 1.478 (3) | C18—C19 | 1.382 (4) |
C7—C8 | 1.482 (4) | C18—H18 | 0.9300 |
C7—H7A | 0.9700 | C19—C20 | 1.377 (4) |
C7—H7B | 0.9700 | C19—H19 | 0.9300 |
C8—H8A | 0.9600 | C20—C21 | 1.368 (4) |
C8—H8B | 0.9600 | C20—H20 | 0.9300 |
C8—H8C | 0.9600 | C21—C22 | 1.378 (4) |
C9—N5 | 1.463 (3) | C21—H21 | 0.9300 |
C9—C10 | 1.486 (5) | C22—H22 | 0.9300 |
C9—H9A | 0.9700 | N1—N2 | 1.377 (3) |
C9—H9B | 0.9700 | N5—N6 | 1.364 (3) |
C10—H10A | 0.9600 | ||
N1—C1—C17 | 121.6 (2) | C12—C11—N2 | 122.1 (2) |
N1—C1—S1 | 115.96 (18) | C13—C12—C11 | 119.6 (2) |
C17—C1—S1 | 122.39 (18) | C13—C12—H12 | 120.2 |
N3—C2—C3 | 108.05 (18) | C11—C12—H12 | 120.2 |
N3—C2—N2 | 111.20 (18) | C14—C13—C12 | 121.4 (3) |
C3—C2—N2 | 114.5 (2) | C14—C13—H13 | 119.3 |
N3—C2—S1 | 111.02 (16) | C12—C13—H13 | 119.3 |
C3—C2—S1 | 110.59 (15) | C15—C14—C13 | 118.6 (3) |
N2—C2—S1 | 101.41 (14) | C15—C14—H14 | 120.7 |
C5—C3—C4 | 104.8 (2) | C13—C14—H14 | 120.7 |
C5—C3—C2 | 121.5 (2) | C14—C15—C16 | 121.3 (3) |
C4—C3—C2 | 133.8 (2) | C14—C15—H15 | 119.3 |
N6—C4—C3 | 111.7 (2) | C16—C15—H15 | 119.3 |
N6—C4—H4 | 124.2 | C15—C16—C11 | 120.0 (3) |
C3—C4—H4 | 124.2 | C15—C16—H16 | 120.0 |
N5—C5—C3 | 107.4 (2) | C11—C16—H16 | 120.0 |
N5—C5—N4 | 124.9 (2) | C18—C17—C22 | 119.0 (2) |
C3—C5—N4 | 127.7 (2) | C18—C17—C1 | 121.3 (2) |
N4—C6—N3 | 129.0 (2) | C22—C17—C1 | 119.6 (2) |
N4—C6—H6 | 115.5 | C17—C18—C19 | 120.6 (3) |
N3—C6—H6 | 115.5 | C17—C18—H18 | 119.7 |
N3—C7—C8 | 114.0 (2) | C19—C18—H18 | 119.7 |
N3—C7—H7A | 108.8 | C20—C19—C18 | 119.9 (3) |
C8—C7—H7A | 108.8 | C20—C19—H19 | 120.1 |
N3—C7—H7B | 108.8 | C18—C19—H19 | 120.1 |
C8—C7—H7B | 108.8 | C21—C20—C19 | 119.8 (3) |
H7A—C7—H7B | 107.6 | C21—C20—H20 | 120.1 |
C7—C8—H8A | 109.5 | C19—C20—H20 | 120.1 |
C7—C8—H8B | 109.5 | C20—C21—C22 | 120.6 (3) |
H8A—C8—H8B | 109.5 | C20—C21—H21 | 119.7 |
C7—C8—H8C | 109.5 | C22—C21—H21 | 119.7 |
H8A—C8—H8C | 109.5 | C21—C22—C17 | 120.1 (3) |
H8B—C8—H8C | 109.5 | C21—C22—H22 | 120.0 |
N5—C9—C10 | 111.5 (3) | C17—C22—H22 | 120.0 |
N5—C9—H9A | 109.3 | C1—N1—N2 | 113.15 (19) |
C10—C9—H9A | 109.3 | N1—N2—C11 | 117.04 (18) |
N5—C9—H9B | 109.3 | N1—N2—C2 | 118.15 (18) |
C10—C9—H9B | 109.3 | C11—N2—C2 | 124.77 (19) |
H9A—C9—H9B | 108.0 | C6—N3—C2 | 122.90 (19) |
C9—C10—H10A | 109.5 | C6—N3—C7 | 118.6 (2) |
C9—C10—H10B | 109.5 | C2—N3—C7 | 118.34 (19) |
H10A—C10—H10B | 109.5 | C6—N4—C5 | 110.84 (19) |
C9—C10—H10C | 109.5 | C5—N5—N6 | 111.18 (19) |
H10A—C10—H10C | 109.5 | C5—N5—C9 | 128.3 (2) |
H10B—C10—H10C | 109.5 | N6—N5—C9 | 120.0 (2) |
C16—C11—C12 | 119.1 (2) | C4—N6—N5 | 105.0 (2) |
C16—C11—N2 | 118.9 (2) | C1—S1—C2 | 91.28 (10) |
Cg1 and Cg2 are the ring centroids of the C17–C22 and C11–C16 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Cg1i | 0.93 | 2.75 | 3.615 (3) | 155 |
C20—H20···Cg2ii | 0.93 | 2.77 | 3.564 (4) | 144 |
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) x−1/2, −y+1/2, −z+1. |
Cg1 and Cg2 are the ring centroids of the C17–C22 and C11–C16 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Cg1i | 0.93 | 2.75 | 3.615 (3) | 155 |
C20—H20···Cg2ii | 0.93 | 2.77 | 3.564 (4) | 144 |
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) x−1/2, −y+1/2, −z+1. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements, and the University Mohammed V, Rabat, Morocco, for financial support.
References
Ahoya, C. A., Daouda, B., Bouhfid, R., Hançali, A., Bousmina, M., Zerzouf, A., El Aouad, R. & Essassi, E. M. (2011). Arkivoc, (ii), 217–226. Google Scholar
Anothane, C. A., Bouhfid, R., Essassi, E. M. & Ng, S. W. (2012). Acta Cryst. E68, o103. CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chern, J.-H., Shia, K.-S., Hsu, T.-A., Tai, C.-L., Lee, C.-C., Lee, Y.-C., Chang, C.-S., Tseng, S.-N. & Shih, S.-R. (2004). Bioorg. Med. Chem. Lett. 14, 2519–2525. CrossRef PubMed CAS Google Scholar
Dinér, P., Alao, J. P., Söderlund, J., Sunnerhagen, P. & Grøtli, M. (2012). J. Med. Chem. 55, 4872–4876. PubMed Google Scholar
El Fal, M., Ramli, Y., Essassi, E. M., Saadi, M. & El Ammari, L. (2014). Acta Cryst. E70, o1038. CSD CrossRef IUCr Journals Google Scholar
El Fal, M., Ramli, Y., Essassi, E. M., Saadi, M. & El Ammari, L. (2015). Acta Cryst. E71, o95–o96. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Schenone, S., Bruno, O., Radi, M. & Botta, M. (2009). Mini-Rev. Org. Chem. 6, 220–233. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Taliani, S., La Motta, C., Mugnaini, L., Simorini, F., Salerno, S., Marini, A. M., Da Settimo, F., Cosconati, S., Cosimelli, B. & Greco, G. (2010). J. Med. Chem. 53, 3954–3963. CrossRef CAS PubMed Google Scholar
Trivedi, A. R., Dholariya, B. H., Vakhariya, C. P., Dodiya, D. K., Ram, H. K., Kataria, V. B., Siddiqui, A. B. & Shah, V. H. (2012). Med. Chem. Res. 21, 1887–1891. CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The pyrazolo[3,4-d]pyrimidine nucleus is considered as a very interesting and versatile scaffold for the synthesis of potential drug candidates acting on a wide range of biological targets (Schenone et al., 2009). Among their many applications, they have been used as kinase inhibitors (Dinér et al., 2012), antiviral agents (Chern et al., 2004), adenosine antagonists (Taliani et al., 2010 and as antitubercular agents (Trivedi et al., 2012). In the search for new compounds with therapeutic interest, we have prepared spiro[pyrazolo[3,4-d]pyrimidine-1,2'-[1,3,4]thiadiazole] derivatives via 1,3-dipolar cycloaddition using diphenyl hydrazonoyl chloride as the precursor for diphenyl nitrilimine, and 1,5-diethyl-1H-pyrazolo [3,4-d]pyrimidin-4(5H)-thione as the dipolarophile (El Fal et al., 2014; El Fal et al., 2015; Ahoya et al., 2011, Anothane et al., 2012).
The molecule of the title compound is built up from two fused five- and six-membered heterocycles linked to two ethyls and to two phenyl rings via the thiadiazole ring as shown in Fig. 1. The pyrazolo[3,4-d]pyrimidine system is virtually planar with the largest deviation from the mean plane being 0.016 (2) Å at N3 and makes dihedral angles of 86.93 (10) and 83.35 (11)° with the mean plane through the first (C11 to C16) and the second (C17 to C22) phenyl rings, respectively. Furthermore, the two phenyl rings are virtually coplanar with the largest deviation from the mean plane of -0.069 (2) Å, and makes a dihedral angle of 9.88 (9)° with the thiadiazole ring. No classic hydrogen bonds are observed in the structure.