Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Ten new N4-substituted 1H-pyrazolo[3,4-d]pyrimidine-4,6-diamines have been synthesized and the structures of nine of them are reported here, falling into two clear groups, those which are stoichiometric hydrates and those which crystallize in solvent-free forms. In each of N4-methyl-N4-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine, C12H12N6 (I), N4-cyclohexyl-N4-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine, C12H18N6 (II), and N4-(3-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine, C11H9ClN6 (III), the molecules are linked into hydrogen-bonded sheets. The molecules of 2-{4-(6-amino-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl}ethanol, C11H17N7O (IV), are linked into a three-dimensional framework, while the structure of N4-methyl-N4-(4-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine monohydrate, C13H14N6·H2O (V), is only two-dimensional despite the presence of five independent hydrogen bonds. The stoichiometric hemihydrates N4-ethyl-N4-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine hemihydrate, C13H14N6·0.5H2O (VI) and N4-(4-methoxyphenyl)-N4-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine hemihydrate, C13H14N6O·0.5H2O (VII), exhibit remarkably similar sheet structures, despite different space groups and Z′ values, Z′ = 0.5 in C2/c for (VI) and Z′ = 1 in P\bar 1 for (VII). N4-4-Benzyl-N4-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine monohydrate, C18H16N6·H2O (VIII), crystallizes with Z′ = 2 in P21/n, and the four independent molecular components are linked into sheets by a total of 11 intermolecular hydrogen bonds. The sheet structure in {4-(pyrrolidin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine-6-amine} ethanol hemisolvate hemihydrate, C9H12N6·0.5C2H6O·0.5H2O (IX), is built from the pyrimidine and water components only; it contains eight independent hydrogen bonds, and it very closely mimics the sheets in (VI) and (VII); the ethanol molecules are pendent from these sheets. The N4-alkyl-N4-aryl-4-aminopyrazolopyrimidine molecules in (I), (V)–(VIII) all adopt very similar conformations, dominated in each case by an intramolecular C—H...π(arene) hydrogen bond: this interaction is absent from (III) where the molecular conformation is entirely different and probably dominated by the intermolecular hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108019903/bm5056sup1.cif
Contains datablocks global, I, II, III, IV, V, VI, VII, VIII, IX

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019903/bm5056Isup2.fcf
Contains datablock I

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019903/bm5056IIsup3.fcf
Contains datablock II

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019903/bm5056IIIsup4.fcf
Contains datablock III

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019903/bm5056IVsup5.fcf
Contains datablock IV

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019903/bm5056Vsup6.fcf
Contains datablock V

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019903/bm5056VIsup7.fcf
Contains datablock VI

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019903/bm5056VIIsup8.fcf
Contains datablock VII

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019903/bm5056VIIIsup9.fcf
Contains datablock VIII

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019903/bm5056IXsup10.fcf
Contains datablock IX

CCDC references: 705604; 705605; 705606; 705607; 705608; 705609; 705610; 705611; 705612

Comment top

In full text version

Experimental top

In full text version

Refinement top

In full text version

Computing details top

For all compounds, data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: Sir2004 (Burla et al., 2005); program(s) used to refine structure: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
In full text version
(I) N4-Methyl-N4-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine top
Crystal data top
C12H12N6F(000) = 504
Mr = 240.28Dx = 1.369 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2674 reflections
a = 10.6661 (12) Åθ = 3.0–27.5°
b = 7.7279 (9) ŵ = 0.09 mm1
c = 14.359 (2) ÅT = 120 K
β = 100.071 (7)°Block, colourless
V = 1165.3 (3) Å30.58 × 0.41 × 0.34 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2674 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1737 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ϕ & ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
h = 1313
Tmin = 0.953, Tmax = 0.970k = 1010
27117 measured reflectionsl = 1818
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0702P)2 + 1.151P]
where P = (Fo2 + 2Fc2)/3
2674 reflections(Δ/σ)max < 0.001
164 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C12H12N6V = 1165.3 (3) Å3
Mr = 240.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.6661 (12) ŵ = 0.09 mm1
b = 7.7279 (9) ÅT = 120 K
c = 14.359 (2) Å0.58 × 0.41 × 0.34 mm
β = 100.071 (7)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2674 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
1737 reflections with I > 2σ(I)
Tmin = 0.953, Tmax = 0.970Rint = 0.054
27117 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 1.10Δρmax = 0.27 e Å3
2674 reflectionsΔρmin = 0.43 e Å3
164 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.61207 (17)0.1677 (2)0.51997 (12)0.0236 (4)
N40.58721 (17)0.5923 (2)0.28872 (13)0.0246 (4)
N70.43838 (17)0.1459 (2)0.39011 (12)0.0231 (4)
N50.43211 (17)0.3819 (2)0.27905 (12)0.0219 (4)
N60.28309 (17)0.1679 (3)0.25756 (13)0.0284 (5)
C3A0.6022 (2)0.3725 (3)0.41199 (15)0.0219 (5)
C410.7043 (2)0.6662 (3)0.33631 (15)0.0224 (5)
C40.5403 (2)0.4506 (3)0.32582 (14)0.0207 (5)
N20.71484 (18)0.2724 (3)0.54971 (13)0.0279 (5)
C7A0.54342 (19)0.2237 (3)0.43802 (14)0.0203 (5)
C450.9324 (2)0.6619 (3)0.36752 (17)0.0298 (5)
C440.9319 (2)0.7872 (3)0.43652 (18)0.0315 (6)
C60.3885 (2)0.2322 (3)0.31138 (15)0.0220 (5)
C30.7090 (2)0.3953 (3)0.48542 (16)0.0276 (5)
C470.5260 (2)0.6711 (3)0.20045 (16)0.0308 (6)
C420.7037 (2)0.7944 (3)0.40308 (16)0.0271 (5)
C460.8186 (2)0.6025 (3)0.31655 (16)0.0274 (5)
C430.8179 (2)0.8547 (3)0.45335 (18)0.0328 (6)
H10.60350.07440.55100.028*
H6A0.26290.20070.19960.034*
H6B0.25050.06990.26870.034*
H451.01080.61700.35530.036*
H441.01010.82670.47230.038*
H30.76850.48730.48790.033*
H47A0.46610.58860.16500.046*
H47B0.59080.70250.16270.046*
H47C0.48000.77520.21410.046*
H420.62540.84100.41450.033*
H460.81850.51850.26820.033*
H430.81800.94270.49960.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0237 (9)0.0245 (10)0.0203 (9)0.0047 (7)0.0025 (7)0.0038 (7)
N40.0273 (10)0.0225 (10)0.0215 (9)0.0056 (8)0.0029 (7)0.0041 (7)
N70.0228 (9)0.0244 (10)0.0204 (9)0.0027 (7)0.0009 (7)0.0023 (7)
N50.0219 (9)0.0218 (9)0.0209 (9)0.0017 (7)0.0005 (7)0.0015 (7)
N60.0276 (10)0.0300 (11)0.0243 (10)0.0099 (8)0.0048 (8)0.0048 (8)
C3A0.0208 (11)0.0241 (11)0.0194 (10)0.0017 (9)0.0001 (8)0.0001 (9)
C410.0245 (11)0.0202 (11)0.0215 (10)0.0034 (9)0.0008 (8)0.0030 (9)
C40.0215 (10)0.0195 (10)0.0207 (10)0.0003 (8)0.0024 (8)0.0011 (8)
N20.0268 (10)0.0285 (10)0.0253 (10)0.0069 (8)0.0041 (8)0.0015 (8)
C7A0.0194 (10)0.0213 (11)0.0196 (10)0.0010 (8)0.0014 (8)0.0001 (8)
C450.0247 (12)0.0327 (13)0.0336 (13)0.0010 (10)0.0091 (10)0.0039 (10)
C440.0255 (12)0.0324 (13)0.0346 (13)0.0077 (10)0.0001 (10)0.0000 (11)
C60.0213 (10)0.0232 (11)0.0203 (10)0.0003 (8)0.0005 (8)0.0008 (9)
C30.0264 (12)0.0289 (12)0.0249 (11)0.0065 (9)0.0030 (9)0.0028 (9)
C470.0329 (13)0.0302 (13)0.0266 (12)0.0056 (10)0.0025 (10)0.0076 (10)
C420.0262 (11)0.0271 (12)0.0277 (12)0.0005 (9)0.0039 (9)0.0020 (10)
C460.0295 (12)0.0269 (12)0.0253 (11)0.0007 (10)0.0038 (9)0.0002 (9)
C430.0325 (13)0.0311 (13)0.0336 (13)0.0044 (10)0.0020 (10)0.0071 (10)
Geometric parameters (Å, º) top
N1—C7A1.344 (3)C41—C421.380 (3)
N1—N21.369 (3)C41—C461.389 (3)
N1—H10.86N2—C31.318 (3)
N4—C41.352 (3)C45—C461.382 (3)
N4—C411.433 (3)C45—C441.386 (3)
N4—C471.454 (3)C45—H450.95
N7—C61.340 (3)C44—C431.383 (3)
N7—C7A1.349 (3)C44—H440.95
N5—C41.339 (3)C3—H30.95
N5—C61.358 (3)C47—H47A0.98
N6—C61.343 (3)C47—H47B0.98
N6—H6A0.86C47—H47C0.98
N6—H6B0.86C42—C431.384 (3)
C3A—C7A1.392 (3)C42—H420.95
C3A—C31.422 (3)C46—H460.95
C3A—C41.430 (3)C43—H430.95
C7A—N1—N2111.51 (18)C44—C45—H45120.1
C7A—N1—H1129.2C43—C44—C45120.1 (2)
N2—N1—H1119.0C43—C44—H44119.9
C4—N4—C41119.13 (17)C45—C44—H44119.9
C4—N4—C47122.81 (18)N7—C6—N6118.1 (2)
C41—N4—C47118.03 (18)N7—C6—N5127.06 (19)
C6—N7—C7A112.36 (18)N6—C6—N5114.87 (19)
C4—N5—C6118.87 (18)N2—C3—C3A111.3 (2)
C6—N6—H6A119.4N2—C3—H3124.3
C6—N6—H6B122.9C3A—C3—H3124.3
H6A—N6—H6B113.5N4—C47—H47A109.5
C7A—C3A—C3104.07 (19)N4—C47—H47B109.5
C7A—C3A—C4114.79 (19)H47A—C47—H47B109.5
C3—C3A—C4141.1 (2)N4—C47—H47C109.5
C42—C41—C46120.5 (2)H47A—C47—H47C109.5
C42—C41—N4120.5 (2)H47B—C47—H47C109.5
C46—C41—N4118.9 (2)C41—C42—C43119.6 (2)
N5—C4—N4118.01 (19)C41—C42—H42120.2
N5—C4—C3A119.60 (19)C43—C42—H42120.2
N4—C4—C3A122.39 (19)C45—C46—C41119.7 (2)
C3—N2—N1105.67 (17)C45—C46—H46120.2
N1—C7A—N7125.4 (2)C41—C46—H46120.2
N1—C7A—C3A107.42 (18)C44—C43—C42120.2 (2)
N7—C7A—C3A127.15 (19)C44—C43—H43119.9
C46—C45—C44119.9 (2)C42—C43—H43119.9
C46—C45—H45120.1
C4—N4—C41—C4291.1 (3)C3—C3A—C7A—N10.1 (2)
C47—N4—C41—C4290.8 (3)C4—C3A—C7A—N1179.53 (18)
C4—N4—C41—C4686.7 (3)C3—C3A—C7A—N7178.7 (2)
C47—N4—C41—C4691.4 (3)C4—C3A—C7A—N71.6 (3)
C6—N5—C4—N4175.18 (19)C46—C45—C44—C431.0 (4)
C6—N5—C4—C3A4.5 (3)C7A—N7—C6—N6179.79 (19)
C41—N4—C4—N5178.66 (19)C7A—N7—C6—N50.5 (3)
C47—N4—C4—N50.6 (3)C4—N5—C6—N73.9 (3)
C41—N4—C4—C3A1.0 (3)C4—N5—C6—N6176.8 (2)
C47—N4—C4—C3A179.0 (2)N1—N2—C3—C3A0.3 (3)
C7A—C3A—C4—N52.0 (3)C7A—C3A—C3—N20.1 (3)
C3—C3A—C4—N5177.5 (3)C4—C3A—C3—N2179.6 (3)
C7A—C3A—C4—N4177.7 (2)C46—C41—C42—C432.7 (3)
C3—C3A—C4—N42.9 (4)N4—C41—C42—C43175.1 (2)
C7A—N1—N2—C30.4 (3)C44—C45—C46—C411.4 (3)
N2—N1—C7A—N7178.6 (2)C42—C41—C46—C453.2 (3)
N2—N1—C7A—C3A0.3 (2)N4—C41—C46—C45174.5 (2)
C6—N7—C7A—N1179.0 (2)C45—C44—C43—C421.6 (4)
C6—N7—C7A—C3A2.3 (3)C41—C42—C43—C440.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N7i0.861.992.841 (3)172
N6—H6A···N2ii0.862.132.982 (3)168
N6—H6B···N5iii0.862.433.164 (3)144
C3—H3···Cg10.952.483.255 (3)138
Symmetry codes: (i) x+1, y, z+1; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y1/2, z+1/2.
(II) N4-(Cyclohexyl)-N4-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine top
Crystal data top
C12H18N6F(000) = 528
Mr = 246.33Dx = 1.300 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2885 reflections
a = 11.2407 (10) Åθ = 3.1–27.5°
b = 7.3654 (5) ŵ = 0.09 mm1
c = 15.8178 (12) ÅT = 120 K
β = 106.005 (7)°Block, colourless
V = 1258.83 (17) Å30.32 × 0.28 × 0.18 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2885 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1763 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.110
ϕ & ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
h = 1414
Tmin = 0.964, Tmax = 0.985k = 99
32264 measured reflectionsl = 2020
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0435P)2 + 1.3394P]
where P = (Fo2 + 2Fc2)/3
2885 reflections(Δ/σ)max < 0.001
164 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C12H18N6V = 1258.83 (17) Å3
Mr = 246.33Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.2407 (10) ŵ = 0.09 mm1
b = 7.3654 (5) ÅT = 120 K
c = 15.8178 (12) Å0.32 × 0.28 × 0.18 mm
β = 106.005 (7)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2885 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
1763 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.985Rint = 0.110
32264 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.142H-atom parameters constrained
S = 1.06Δρmax = 0.29 e Å3
2885 reflectionsΔρmin = 0.34 e Å3
164 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.50121 (18)0.1950 (3)0.56711 (12)0.0193 (5)
N20.51249 (18)0.3163 (3)0.63479 (12)0.0212 (5)
N50.21659 (18)0.3765 (3)0.37242 (12)0.0187 (4)
N70.37379 (18)0.1458 (3)0.42100 (12)0.0170 (4)
N40.18037 (19)0.6089 (3)0.45963 (13)0.0210 (5)
N60.2389 (2)0.1435 (3)0.28273 (13)0.0259 (5)
C30.4245 (2)0.4373 (3)0.60584 (15)0.0209 (5)
C3A0.3511 (2)0.3957 (3)0.51885 (14)0.0172 (5)
C40.2487 (2)0.4622 (3)0.45064 (15)0.0179 (5)
C60.2785 (2)0.2243 (3)0.36188 (14)0.0173 (5)
C7A0.4064 (2)0.2389 (3)0.49745 (14)0.0158 (5)
C410.1923 (2)0.6918 (3)0.54590 (16)0.0216 (5)
C420.0670 (2)0.7503 (4)0.55806 (16)0.0254 (6)
C430.0843 (2)0.8223 (4)0.65146 (17)0.0270 (6)
C440.1767 (3)0.9793 (4)0.67206 (18)0.0304 (6)
C450.3009 (2)0.9244 (4)0.65707 (17)0.0283 (6)
C460.2824 (2)0.8508 (3)0.56422 (16)0.0252 (6)
C470.0930 (3)0.6881 (4)0.38227 (16)0.0304 (6)
H10.54500.09750.57630.023*
H6A0.17140.17900.24590.031*
H6B0.27500.04560.27340.031*
H30.41140.53970.63870.025*
H410.22690.59700.59130.026*
H42A0.03020.84610.51490.031*
H42B0.00970.64540.54750.031*
H43A0.00350.86410.65790.032*
H43B0.11420.72290.69420.032*
H44A0.19001.01710.73400.037*
H44B0.14221.08420.63400.037*
H45A0.35641.03120.66610.034*
H45B0.34060.83030.70040.034*
H46A0.25020.94870.52110.030*
H46B0.36310.81080.55700.030*
H47A0.00900.64750.37940.046*
H47B0.11450.64900.32910.046*
H47C0.09710.82080.38650.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0215 (11)0.0182 (10)0.0164 (10)0.0054 (8)0.0025 (8)0.0021 (8)
N20.0215 (11)0.0222 (11)0.0185 (10)0.0012 (9)0.0032 (8)0.0046 (9)
N50.0177 (10)0.0187 (10)0.0189 (10)0.0012 (8)0.0038 (8)0.0003 (8)
N70.0176 (10)0.0160 (10)0.0162 (10)0.0031 (8)0.0024 (8)0.0005 (8)
N40.0240 (11)0.0181 (11)0.0204 (11)0.0063 (8)0.0056 (9)0.0004 (8)
N60.0249 (12)0.0274 (12)0.0209 (11)0.0109 (9)0.0014 (9)0.0048 (9)
C30.0240 (13)0.0176 (12)0.0208 (12)0.0000 (10)0.0060 (10)0.0028 (10)
C3A0.0191 (12)0.0153 (11)0.0179 (12)0.0014 (9)0.0063 (10)0.0001 (9)
C40.0188 (12)0.0161 (12)0.0206 (12)0.0008 (9)0.0083 (10)0.0027 (10)
C60.0182 (12)0.0170 (12)0.0163 (12)0.0000 (9)0.0041 (9)0.0003 (10)
C7A0.0146 (11)0.0166 (11)0.0155 (11)0.0006 (9)0.0030 (9)0.0029 (9)
C410.0246 (13)0.0194 (12)0.0214 (12)0.0061 (10)0.0075 (10)0.0010 (10)
C420.0258 (13)0.0225 (13)0.0292 (14)0.0011 (11)0.0098 (11)0.0011 (11)
C430.0264 (14)0.0274 (14)0.0304 (14)0.0022 (11)0.0131 (11)0.0041 (11)
C440.0357 (16)0.0288 (14)0.0293 (15)0.0015 (12)0.0130 (12)0.0085 (12)
C450.0283 (14)0.0269 (14)0.0312 (14)0.0045 (11)0.0110 (12)0.0059 (12)
C460.0276 (14)0.0234 (13)0.0273 (13)0.0004 (11)0.0122 (11)0.0002 (11)
C470.0346 (16)0.0277 (14)0.0264 (14)0.0152 (12)0.0043 (12)0.0040 (11)
Geometric parameters (Å, º) top
N1—C7A1.344 (3)C41—C421.535 (3)
N1—N21.373 (3)C41—H411.00
N1—H10.86C42—C431.531 (3)
N2—C31.316 (3)C42—H42A0.99
N5—C41.347 (3)C42—H42B0.99
N5—C61.354 (3)C43—C441.528 (4)
N7—C61.343 (3)C43—H43A0.99
N7—C7A1.350 (3)C43—H43B0.99
N4—C41.356 (3)C44—C451.533 (4)
N4—C471.463 (3)C44—H44A0.99
N4—C411.467 (3)C44—H44B0.99
N6—C61.347 (3)C45—C461.525 (3)
N6—H6A0.86C45—H45A0.99
N6—H6B0.86C45—H45B0.99
C3—C3A1.429 (3)C46—H46A0.99
C3—H30.95C46—H46B0.99
C3A—C7A1.397 (3)C47—H47A0.98
C3A—C41.429 (3)C47—H47B0.98
C41—C461.523 (3)C47—H47C0.98
C7A—N1—N2111.39 (19)C41—C42—H42A109.7
C7A—N1—H1128.8C43—C42—H42B109.7
N2—N1—H1119.1C41—C42—H42B109.7
C3—N2—N1105.69 (18)H42A—C42—H42B108.2
C4—N5—C6119.0 (2)C44—C43—C42111.5 (2)
C6—N7—C7A111.89 (19)C44—C43—H43A109.3
C4—N4—C47120.0 (2)C42—C43—H43A109.3
C4—N4—C41121.34 (19)C44—C43—H43B109.3
C47—N4—C41118.70 (19)C42—C43—H43B109.3
C6—N6—H6A120.0H43A—C43—H43B108.0
C6—N6—H6B118.6C43—C44—C45111.2 (2)
H6A—N6—H6B120.6C43—C44—H44A109.4
N2—C3—C3A111.7 (2)C45—C44—H44A109.4
N2—C3—H3124.2C43—C44—H44B109.4
C3A—C3—H3124.2C45—C44—H44B109.4
C7A—C3A—C4114.8 (2)H44A—C44—H44B108.0
C7A—C3A—C3103.46 (19)C46—C45—C44110.8 (2)
C4—C3A—C3141.7 (2)C46—C45—H45A109.5
N5—C4—N4117.0 (2)C44—C45—H45A109.5
N5—C4—C3A119.3 (2)C46—C45—H45B109.5
N4—C4—C3A123.7 (2)C44—C45—H45B109.5
N7—C6—N6117.0 (2)H45A—C45—H45B108.1
N7—C6—N5127.5 (2)C41—C46—C45111.3 (2)
N6—C6—N5115.5 (2)C41—C46—H46A109.4
N1—C7A—N7124.8 (2)C45—C46—H46A109.4
N1—C7A—C3A107.8 (2)C41—C46—H46B109.4
N7—C7A—C3A127.4 (2)C45—C46—H46B109.4
N4—C41—C46112.52 (19)H46A—C46—H46B108.0
N4—C41—C42112.4 (2)N4—C47—H47A109.5
C46—C41—C42110.2 (2)N4—C47—H47B109.5
N4—C41—H41107.1H47A—C47—H47B109.5
C46—C41—H41107.1N4—C47—H47C109.5
C42—C41—H41107.1H47A—C47—H47C109.5
C43—C42—C41110.0 (2)H47B—C47—H47C109.5
C43—C42—H42A109.7
C7A—N1—N2—C30.8 (3)N2—N1—C7A—C3A0.2 (3)
N1—N2—C3—C3A1.5 (3)C6—N7—C7A—N1177.6 (2)
N2—C3—C3A—C7A1.5 (3)C6—N7—C7A—C3A1.6 (3)
N2—C3—C3A—C4178.9 (3)C4—C3A—C7A—N1179.2 (2)
C6—N5—C4—N4176.9 (2)C3—C3A—C7A—N11.0 (2)
C6—N5—C4—C3A3.1 (3)C4—C3A—C7A—N70.1 (3)
C47—N4—C4—N511.6 (3)C3—C3A—C7A—N7178.4 (2)
C41—N4—C4—N5168.7 (2)C4—N4—C41—C4694.9 (3)
C47—N4—C4—C3A168.4 (2)C47—N4—C41—C4684.8 (3)
C41—N4—C4—C3A11.2 (3)C4—N4—C41—C42140.0 (2)
C7A—C3A—C4—N52.3 (3)C47—N4—C41—C4240.4 (3)
C3—C3A—C4—N5174.9 (3)N4—C41—C42—C43175.7 (2)
C7A—C3A—C4—N4177.7 (2)C46—C41—C42—C4357.9 (3)
C3—C3A—C4—N45.1 (5)C41—C42—C43—C4456.8 (3)
C7A—N7—C6—N6179.5 (2)C42—C43—C44—C4555.3 (3)
C7A—N7—C6—N50.7 (3)C43—C44—C45—C4654.5 (3)
C4—N5—C6—N71.6 (4)N4—C41—C46—C45175.4 (2)
C4—N5—C6—N6178.2 (2)C42—C41—C46—C4558.3 (3)
N2—N1—C7A—N7179.2 (2)C44—C45—C46—C4156.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N7i0.862.012.858 (3)170
N6—H6A···N2ii0.862.132.959 (3)161
N6—H6B···N5iii0.862.653.289 (3)133
Symmetry codes: (i) x+1, y, z+1; (ii) x1/2, y+1/2, z1/2; (iii) x+1/2, y1/2, z+1/2.
(III) N4-(3-Chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine top
Crystal data top
C11H9ClN6F(000) = 536
Mr = 260.69Dx = 1.580 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2515 reflections
a = 11.1960 (8) Åθ = 3.1–27.5°
b = 8.5040 (8) ŵ = 0.34 mm1
c = 13.3815 (12) ÅT = 120 K
β = 120.674 (5)°Lath, colourless
V = 1095.80 (16) Å30.55 × 0.21 × 0.10 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2515 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1452 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.108
ϕ & ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
h = 1414
Tmin = 0.836, Tmax = 0.967k = 1111
26526 measured reflectionsl = 1717
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0954P)2 + 0.4665P]
where P = (Fo2 + 2Fc2)/3
2515 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.47 e Å3
Crystal data top
C11H9ClN6V = 1095.80 (16) Å3
Mr = 260.69Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.1960 (8) ŵ = 0.34 mm1
b = 8.5040 (8) ÅT = 120 K
c = 13.3815 (12) Å0.55 × 0.21 × 0.10 mm
β = 120.674 (5)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2515 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
1452 reflections with I > 2σ(I)
Tmin = 0.836, Tmax = 0.967Rint = 0.108
26526 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.183H-atom parameters constrained
S = 1.06Δρmax = 0.42 e Å3
2515 reflectionsΔρmin = 0.47 e Å3
163 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl430.94145 (10)0.08799 (10)0.86327 (7)0.0304 (3)
N10.4781 (3)0.8769 (3)0.3832 (2)0.0227 (7)
N20.4385 (3)0.8045 (3)0.2788 (2)0.0237 (7)
N40.6910 (3)0.3905 (3)0.4744 (2)0.0216 (7)
N50.7278 (3)0.5627 (3)0.6231 (2)0.0212 (7)
N60.7696 (3)0.7259 (4)0.7724 (2)0.0299 (8)
N70.6187 (3)0.8196 (3)0.5878 (2)0.0218 (7)
C30.5002 (3)0.6654 (4)0.3064 (3)0.0230 (8)
C3A0.5801 (3)0.6442 (4)0.4277 (3)0.0203 (7)
C40.6675 (3)0.5298 (4)0.5100 (3)0.0194 (7)
C60.7025 (3)0.7030 (4)0.6557 (3)0.0209 (7)
C7A0.5619 (3)0.7830 (4)0.4740 (3)0.0212 (8)
C410.7684 (3)0.2593 (4)0.5412 (3)0.0201 (7)
C420.8109 (3)0.2404 (4)0.6580 (3)0.0212 (8)
C430.8862 (3)0.1070 (4)0.7159 (3)0.0229 (8)
C440.9164 (3)0.0108 (4)0.6613 (3)0.0238 (8)
C450.8698 (3)0.0073 (4)0.5435 (3)0.0257 (8)
C460.7984 (4)0.1417 (4)0.4845 (3)0.0238 (8)
H10.44040.96620.38030.027*
H40.65110.37680.40050.026*
H6A0.83420.65690.80700.036*
H6B0.78500.81830.80250.036*
H30.49160.58920.25120.028*
H420.78880.31740.69760.025*
H440.96740.10140.70270.029*
H450.88710.07310.50320.031*
H460.76970.15380.40480.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl430.0392 (6)0.0291 (5)0.0193 (5)0.0039 (4)0.0122 (4)0.0030 (4)
N10.0236 (15)0.0241 (16)0.0195 (15)0.0009 (12)0.0104 (13)0.0003 (12)
N20.0269 (16)0.0271 (17)0.0168 (15)0.0019 (13)0.0108 (13)0.0008 (12)
N40.0263 (16)0.0217 (16)0.0126 (14)0.0027 (12)0.0069 (12)0.0000 (11)
N50.0234 (15)0.0201 (15)0.0173 (14)0.0014 (12)0.0084 (12)0.0003 (12)
N60.0392 (19)0.0262 (17)0.0184 (16)0.0044 (14)0.0105 (14)0.0027 (13)
N70.0235 (15)0.0227 (16)0.0161 (14)0.0025 (12)0.0079 (12)0.0001 (12)
C30.0257 (19)0.0227 (19)0.0177 (17)0.0022 (15)0.0089 (15)0.0026 (15)
C3A0.0206 (17)0.0203 (17)0.0167 (17)0.0008 (14)0.0071 (14)0.0001 (14)
C40.0194 (17)0.0194 (18)0.0210 (17)0.0012 (14)0.0114 (14)0.0000 (14)
C60.0220 (18)0.0203 (18)0.0186 (17)0.0004 (15)0.0092 (15)0.0000 (14)
C7A0.0199 (18)0.0212 (19)0.0220 (18)0.0008 (14)0.0103 (15)0.0006 (14)
C410.0161 (16)0.0202 (18)0.0213 (17)0.0043 (14)0.0077 (14)0.0014 (14)
C420.0213 (18)0.0219 (18)0.0204 (17)0.0021 (14)0.0106 (15)0.0041 (14)
C430.0220 (18)0.025 (2)0.0175 (17)0.0028 (15)0.0070 (15)0.0004 (14)
C440.0256 (18)0.0175 (18)0.0266 (19)0.0041 (15)0.0121 (16)0.0027 (15)
C450.0284 (19)0.0215 (19)0.0284 (19)0.0018 (16)0.0153 (16)0.0026 (16)
C460.0286 (19)0.0237 (19)0.0179 (18)0.0006 (15)0.0111 (15)0.0029 (15)
Geometric parameters (Å, º) top
Cl43—C431.748 (3)C3—C3A1.408 (4)
N1—C7A1.354 (4)C3—H30.95
N1—N21.377 (4)C3A—C7A1.395 (5)
N1—H10.86C3A—C41.421 (5)
N2—C31.324 (4)C41—C421.392 (4)
N4—C41.352 (4)C41—C461.396 (5)
N4—C411.415 (4)C42—C431.390 (5)
N4—H40.86C42—H420.95
N5—C41.334 (4)C43—C441.380 (5)
N5—C61.349 (4)C44—C451.394 (5)
N6—C61.358 (4)C44—H440.95
N6—H6A0.8601C45—C461.387 (5)
N6—H6B0.86C45—H450.95
N7—C61.349 (4)C46—H460.95
N7—C7A1.353 (4)
C7A—N1—N2111.3 (3)N5—C6—N6114.5 (3)
C7A—N1—H1131.4N7—C7A—N1125.9 (3)
N2—N1—H1116.9N7—C7A—C3A127.1 (3)
C3—N2—N1105.3 (3)N1—C7A—C3A107.0 (3)
C4—N4—C41129.4 (3)C42—C41—C46119.2 (3)
C4—N4—H4116.3C42—C41—N4123.3 (3)
C41—N4—H4114.3C46—C41—N4117.4 (3)
C4—N5—C6118.9 (3)C43—C42—C41118.8 (3)
C6—N6—H6A110.0C43—C42—H42120.6
C6—N6—H6B122.1C41—C42—H42120.6
H6A—N6—H6B117.3C44—C43—C42122.8 (3)
C6—N7—C7A110.8 (3)C44—C43—Cl43119.3 (3)
N2—C3—C3A111.7 (3)C42—C43—Cl43117.9 (3)
N2—C3—H3124.1C43—C44—C45117.8 (3)
C3A—C3—H3124.1C43—C44—H44121.1
C7A—C3A—C3104.6 (3)C45—C44—H44121.1
C7A—C3A—C4115.7 (3)C46—C45—C44120.6 (3)
C3—C3A—C4139.7 (3)C46—C45—H45119.7
N5—C4—N4120.4 (3)C44—C45—H45119.7
N5—C4—C3A119.1 (3)C45—C46—C41120.7 (3)
N4—C4—C3A120.5 (3)C45—C46—H46119.7
N7—C6—N5128.3 (3)C41—C46—H46119.7
N7—C6—N6117.2 (3)
C7A—N1—N2—C30.6 (4)N2—N1—C7A—N7179.8 (3)
N1—N2—C3—C3A0.1 (4)N2—N1—C7A—C3A1.0 (4)
N2—C3—C3A—C7A0.5 (4)C3—C3A—C7A—N7179.7 (3)
N2—C3—C3A—C4179.5 (4)C4—C3A—C7A—N70.3 (5)
C6—N5—C4—N4179.8 (3)C3—C3A—C7A—N10.8 (4)
C6—N5—C4—C3A0.8 (5)C4—C3A—C7A—N1179.1 (3)
C41—N4—C4—N54.3 (5)C4—N4—C41—C4214.2 (5)
C41—N4—C4—C3A176.7 (3)C4—N4—C41—C46168.0 (3)
C7A—C3A—C4—N51.6 (5)C46—C41—C42—C432.1 (5)
C3—C3A—C4—N5178.4 (4)N4—C41—C42—C43179.8 (3)
C7A—C3A—C4—N4179.4 (3)C41—C42—C43—C442.4 (5)
C3—C3A—C4—N40.6 (6)C41—C42—C43—Cl43178.7 (2)
C7A—N7—C6—N52.8 (5)C42—C43—C44—C450.6 (5)
C7A—N7—C6—N6178.3 (3)Cl43—C43—C44—C45179.5 (3)
C4—N5—C6—N71.7 (5)C43—C44—C45—C461.6 (5)
C4—N5—C6—N6179.4 (3)C44—C45—C46—C411.8 (5)
C6—N7—C7A—N1176.9 (3)C42—C41—C46—C450.0 (5)
C6—N7—C7A—C3A1.7 (5)N4—C41—C46—C45177.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N7i0.862.062.901 (4)167
N4—H4···N2ii0.862.173.017 (4)171
N6—H6B···Cl43iii0.862.743.504 (3)148
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y1/2, z+1/2; (iii) x, y+1, z.
(IV) 2-[4-(6-Amino-1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazin-1-yl]ethanol top
Crystal data top
C11H17N7OF(000) = 1120
Mr = 263.32Dx = 1.393 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2877 reflections
a = 7.0297 (9) Åθ = 3.0–27.5°
b = 13.859 (3) ŵ = 0.10 mm1
c = 25.766 (6) ÅT = 120 K
V = 2510.2 (9) Å3Lath, colourless
Z = 80.20 × 0.10 × 0.08 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2877 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1479 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.171
ϕ & ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
h = 99
Tmin = 0.985, Tmax = 0.992k = 1818
59170 measured reflectionsl = 3333
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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.224H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.1298P)2]
where P = (Fo2 + 2Fc2)/3
2877 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C11H17N7OV = 2510.2 (9) Å3
Mr = 263.32Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 7.0297 (9) ŵ = 0.10 mm1
b = 13.859 (3) ÅT = 120 K
c = 25.766 (6) Å0.20 × 0.10 × 0.08 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2877 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
1479 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.992Rint = 0.171
59170 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0710 restraints
wR(F2) = 0.224H-atom parameters constrained
S = 1.01Δρmax = 0.33 e Å3
2877 reflectionsΔρmin = 0.36 e Å3
172 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O40.0758 (3)0.70074 (16)0.30495 (9)0.0357 (6)
N11.0456 (4)0.24499 (18)0.33828 (10)0.0282 (7)
N20.9778 (4)0.28387 (19)0.29284 (10)0.0295 (7)
N50.6912 (3)0.34275 (17)0.44779 (10)0.0266 (6)
N60.8470 (4)0.25795 (19)0.51087 (10)0.0314 (7)
N70.9701 (4)0.24650 (17)0.42870 (10)0.0266 (6)
N410.5186 (4)0.42918 (18)0.38860 (10)0.0275 (6)
N440.2016 (4)0.55466 (18)0.37198 (10)0.0280 (7)
C30.8265 (4)0.3342 (2)0.30558 (12)0.0282 (8)
C3A0.7919 (4)0.3303 (2)0.35955 (12)0.0247 (7)
C40.6661 (4)0.3680 (2)0.39809 (12)0.0250 (7)
C60.8372 (4)0.2819 (2)0.46053 (13)0.0279 (8)
C7A0.9382 (4)0.2714 (2)0.37915 (12)0.0255 (8)
C110.0507 (4)0.6231 (2)0.31542 (12)0.0304 (8)
C180.0004 (4)0.5813 (2)0.36710 (12)0.0288 (8)
C420.4439 (4)0.4902 (2)0.43035 (13)0.0296 (8)
C430.2361 (5)0.5107 (2)0.42264 (12)0.0298 (8)
C450.2620 (4)0.4865 (2)0.33192 (12)0.0286 (8)
C460.4717 (4)0.4626 (2)0.33674 (12)0.0308 (8)
H40.04770.71820.27550.054*
H11.14470.20860.33730.034*
H6B0.93720.22270.52300.038*
H6A0.75320.27290.53070.038*
H30.75010.36880.28160.034*
H11A0.03910.57310.28810.036*
H11B0.18370.64660.31580.036*
H18A0.03210.62880.39440.035*
H18B0.07920.52310.37310.035*
H42A0.51520.55170.43120.035*
H42B0.46260.45730.46410.035*
H43A0.16320.44980.42530.036*
H43B0.19110.55470.45030.036*
H45A0.23720.51470.29730.034*
H45B0.18650.42650.33500.034*
H46A0.50510.41190.31120.037*
H46B0.54790.52070.32860.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0350 (14)0.0362 (14)0.0358 (14)0.0073 (10)0.0050 (11)0.0122 (10)
N10.0291 (14)0.0295 (14)0.0262 (15)0.0059 (12)0.0005 (12)0.0009 (12)
N20.0319 (15)0.0337 (15)0.0230 (15)0.0003 (13)0.0022 (12)0.0020 (12)
N50.0300 (15)0.0237 (13)0.0260 (15)0.0022 (11)0.0006 (11)0.0030 (11)
N60.0310 (15)0.0379 (16)0.0254 (16)0.0082 (13)0.0033 (12)0.0075 (13)
N70.0274 (14)0.0258 (14)0.0264 (15)0.0020 (12)0.0003 (12)0.0006 (11)
N410.0315 (15)0.0278 (15)0.0231 (15)0.0042 (12)0.0008 (11)0.0014 (11)
N440.0310 (15)0.0258 (14)0.0271 (16)0.0037 (12)0.0011 (11)0.0003 (11)
C30.0292 (17)0.0277 (17)0.0276 (19)0.0015 (15)0.0019 (14)0.0007 (14)
C3A0.0252 (16)0.0261 (16)0.0228 (17)0.0001 (14)0.0012 (13)0.0009 (13)
C40.0263 (16)0.0227 (16)0.0259 (18)0.0044 (14)0.0012 (13)0.0001 (14)
C60.0283 (17)0.0267 (16)0.0287 (19)0.0025 (14)0.0010 (14)0.0011 (14)
C7A0.0272 (17)0.0248 (17)0.0245 (18)0.0037 (13)0.0013 (14)0.0019 (13)
C110.0269 (17)0.0245 (17)0.040 (2)0.0012 (14)0.0002 (15)0.0028 (15)
C180.0291 (18)0.0248 (17)0.033 (2)0.0002 (14)0.0006 (14)0.0039 (14)
C420.0345 (18)0.0280 (17)0.0263 (18)0.0053 (15)0.0020 (14)0.0021 (14)
C430.0392 (19)0.0273 (17)0.0227 (18)0.0031 (15)0.0016 (14)0.0006 (14)
C450.0318 (18)0.0295 (17)0.0245 (18)0.0009 (15)0.0008 (14)0.0018 (14)
C460.0378 (19)0.0334 (18)0.0212 (18)0.0072 (15)0.0010 (14)0.0008 (14)
Geometric parameters (Å, º) top
O4—C111.422 (4)C3—C3A1.413 (4)
O4—H40.82C3—H30.95
N1—C7A1.346 (4)C3A—C7A1.407 (4)
N1—N21.374 (3)C3A—C41.429 (4)
N1—H10.86C11—C181.495 (4)
N2—C31.313 (4)C11—H11A0.99
N5—C41.339 (4)C11—H11B0.99
N5—C61.368 (4)C18—H18A0.99
N6—C61.341 (4)C18—H18B0.99
N6—H6B0.86C42—C431.502 (4)
N6—H6A0.86C42—H42A0.99
N7—C61.337 (4)C42—H42B0.99
N7—C7A1.341 (4)C43—H43A0.99
N41—C41.361 (4)C43—H43B0.99
N41—C461.452 (4)C45—C461.516 (4)
N41—C421.465 (4)C45—H45A0.99
N44—C431.461 (4)C45—H45B0.99
N44—C451.462 (4)C46—H46A0.99
N44—C181.472 (4)C46—H46B0.99
C11—O4—H4104.3O4—C11—H11B110.0
C7A—N1—N2111.4 (3)C18—C11—H11B110.0
C7A—N1—H1129.5H11A—C11—H11B108.4
N2—N1—H1119.1N44—C18—C11113.7 (3)
C3—N2—N1106.0 (3)N44—C18—H18A108.8
C4—N5—C6119.3 (3)C11—C18—H18A108.8
C6—N6—H6B122.0N44—C18—H18B108.8
C6—N6—H6A118.5C11—C18—H18B108.8
H6B—N6—H6A119.1H18A—C18—H18B107.7
C6—N7—C7A111.9 (3)N41—C42—C43111.2 (3)
C4—N41—C46122.5 (3)N41—C42—H42A109.4
C4—N41—C42120.0 (3)C43—C42—H42A109.4
C46—N41—C42114.2 (2)N41—C42—H42B109.4
C43—N44—C45108.2 (2)C43—C42—H42B109.4
C43—N44—C18109.9 (2)H42A—C42—H42B108.0
C45—N44—C18112.4 (2)N44—C43—C42111.0 (3)
N2—C3—C3A111.4 (3)N44—C43—H43A109.4
N2—C3—H3124.3C42—C43—H43A109.4
C3A—C3—H3124.3N44—C43—H43B109.4
C7A—C3A—C3104.5 (3)C42—C43—H43B109.4
C7A—C3A—C4114.5 (3)H43A—C43—H43B108.0
C3—C3A—C4141.0 (3)N44—C45—C46111.5 (3)
N5—C4—N41115.8 (3)N44—C45—H45A109.3
N5—C4—C3A119.2 (3)C46—C45—H45A109.3
N41—C4—C3A125.0 (3)N44—C45—H45B109.3
N7—C6—N6117.8 (3)C46—C45—H45B109.3
N7—C6—N5127.1 (3)H45A—C45—H45B108.0
N6—C6—N5115.0 (3)N41—C46—C45111.5 (3)
N7—C7A—N1125.5 (3)N41—C46—H46A109.3
N7—C7A—C3A127.8 (3)C45—C46—H46A109.3
N1—C7A—C3A106.7 (3)N41—C46—H46B109.3
O4—C11—C18108.3 (2)C45—C46—H46B109.3
O4—C11—H11A110.0H46A—C46—H46B108.0
C18—C11—H11A110.0
C7A—N1—N2—C30.4 (3)N2—N1—C7A—N7178.7 (3)
N1—N2—C3—C3A0.4 (3)N2—N1—C7A—C3A0.2 (3)
N2—C3—C3A—C7A0.3 (3)C3—C3A—C7A—N7178.9 (3)
N2—C3—C3A—C4177.0 (4)C4—C3A—C7A—N70.8 (5)
C6—N5—C4—N41179.6 (3)C3—C3A—C7A—N10.0 (3)
C6—N5—C4—C3A0.3 (4)C4—C3A—C7A—N1178.1 (3)
C46—N41—C4—N5179.4 (3)C43—N44—C18—C11177.5 (3)
C42—N41—C4—N522.2 (4)C45—N44—C18—C1156.9 (3)
C46—N41—C4—C3A0.7 (5)O4—C11—C18—N4453.0 (3)
C42—N41—C4—C3A157.7 (3)C4—N41—C42—C43150.4 (3)
C7A—C3A—C4—N52.3 (4)C46—N41—C42—C4349.6 (4)
C3—C3A—C4—N5179.4 (4)C45—N44—C43—C4261.4 (3)
C7A—C3A—C4—N41177.6 (3)C18—N44—C43—C42175.4 (2)
C3—C3A—C4—N410.5 (6)N41—C42—C43—N4456.1 (3)
C7A—N7—C6—N6176.5 (3)C43—N44—C45—C4660.1 (3)
C7A—N7—C6—N55.0 (4)C18—N44—C45—C46178.3 (2)
C4—N5—C6—N73.8 (5)C4—N41—C46—C45152.2 (3)
C4—N5—C6—N6177.7 (3)C42—N41—C46—C4548.3 (3)
C6—N7—C7A—N1178.7 (3)N44—C45—C46—N4153.8 (3)
C6—N7—C7A—C3A2.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.862.142.863 (3)142
N1—H1···N44i0.862.553.297 (4)145
N6—H6A···N7ii0.862.263.074 (4)157
N6—H6B···N5iii0.862.142.990 (4)170
O4—H4···N2iv0.821.992.796 (3)167
Symmetry codes: (i) x+3/2, y1/2, z; (ii) x1/2, y+1/2, z+1; (iii) x+1/2, y+1/2, z+1; (iv) x+1, y+1/2, z+1/2.
(V) N4-Methyl-N4-(4-phenylmethyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine monohydrate top
Crystal data top
C13H14N6·H2OF(000) = 1152
Mr = 272.32Dx = 1.363 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3046 reflections
a = 16.5577 (12) Åθ = 3.3–27.5°
b = 8.6833 (3) ŵ = 0.09 mm1
c = 18.4640 (13) ÅT = 120 K
V = 2654.7 (3) Å3Block, colourless
Z = 80.37 × 0.24 × 0.23 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
3046 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode2146 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
ϕ & ω scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
h = 2121
Tmin = 0.969, Tmax = 0.979k = 1111
61337 measured reflectionsl = 2323
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0501P)2 + 1.7622P]
where P = (Fo2 + 2Fc2)/3
3046 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C13H14N6·H2OV = 2654.7 (3) Å3
Mr = 272.32Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 16.5577 (12) ŵ = 0.09 mm1
b = 8.6833 (3) ÅT = 120 K
c = 18.4640 (13) Å0.37 × 0.24 × 0.23 mm
Data collection top
Bruker-Nonius KappaCCD
diffractometer
3046 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
2146 reflections with I > 2σ(I)
Tmin = 0.969, Tmax = 0.979Rint = 0.066
61337 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.09Δρmax = 0.26 e Å3
3046 reflectionsΔρmin = 0.29 e Å3
183 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.45042 (9)0.75734 (17)0.43453 (8)0.0197 (3)
N20.52896 (9)0.76445 (17)0.40995 (8)0.0214 (3)
N40.50382 (8)0.26531 (16)0.34624 (8)0.0201 (3)
N50.38597 (8)0.31554 (16)0.40814 (8)0.0184 (3)
N60.26251 (9)0.36047 (17)0.46060 (8)0.0246 (4)
N70.34479 (9)0.57044 (16)0.44702 (8)0.0193 (3)
C30.54657 (11)0.6244 (2)0.38710 (9)0.0206 (4)
C3A0.48052 (10)0.52248 (19)0.39677 (9)0.0180 (4)
C40.45786 (10)0.36621 (19)0.38387 (9)0.0174 (4)
C60.33342 (10)0.4186 (2)0.43784 (9)0.0184 (4)
C7A0.41980 (10)0.61376 (19)0.42747 (9)0.0179 (4)
C410.58589 (10)0.29925 (19)0.32738 (9)0.0190 (4)
C420.64458 (11)0.3072 (2)0.38076 (10)0.0233 (4)
C430.72371 (11)0.3429 (2)0.36250 (10)0.0244 (4)
C440.74590 (11)0.3677 (2)0.29099 (10)0.0226 (4)
C450.68651 (11)0.3531 (2)0.23748 (10)0.0237 (4)
C460.60733 (11)0.3189 (2)0.25528 (10)0.0208 (4)
C470.83125 (11)0.4100 (2)0.27156 (11)0.0300 (4)
C480.47283 (11)0.1145 (2)0.32465 (10)0.0239 (4)
O10.61376 (7)0.96207 (14)0.50869 (7)0.0222 (3)
H10.42880.83960.45190.024*
H6B0.22630.42070.47830.030*
H6A0.25020.26550.45300.030*
H30.59710.59560.36680.025*
H420.63060.28820.42990.028*
H430.76330.35050.39960.029*
H450.70080.36700.18810.028*
H460.56780.30880.21830.025*
H47A0.83560.42300.21900.036*0.50
H47B0.84590.50670.29570.036*0.50
H47C0.86790.32810.28740.036*0.50
H47D0.86400.41550.31570.036*0.50
H47E0.85370.33180.23900.036*0.50
H47F0.83170.51040.24730.036*0.50
H48A0.41370.11720.32390.036*
H48B0.49100.03650.35940.036*
H48C0.49300.08870.27630.036*
H1A0.59410.92270.47230.033*
H1B0.61720.88970.53710.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0203 (7)0.0155 (7)0.0233 (7)0.0006 (6)0.0014 (6)0.0026 (6)
N20.0186 (7)0.0210 (8)0.0247 (8)0.0021 (6)0.0013 (6)0.0006 (6)
N40.0184 (7)0.0163 (7)0.0256 (8)0.0006 (6)0.0017 (6)0.0039 (6)
N50.0177 (7)0.0166 (7)0.0210 (7)0.0007 (6)0.0010 (6)0.0015 (6)
N60.0207 (8)0.0180 (7)0.0351 (9)0.0008 (6)0.0067 (7)0.0033 (6)
N70.0201 (7)0.0160 (7)0.0219 (7)0.0006 (6)0.0012 (6)0.0016 (6)
C30.0211 (9)0.0185 (9)0.0221 (9)0.0008 (7)0.0004 (7)0.0013 (7)
C3A0.0197 (8)0.0180 (8)0.0163 (8)0.0007 (7)0.0005 (7)0.0016 (6)
C40.0187 (8)0.0177 (8)0.0157 (8)0.0017 (7)0.0018 (7)0.0007 (6)
C60.0186 (8)0.0184 (8)0.0183 (8)0.0004 (7)0.0008 (7)0.0001 (7)
C7A0.0200 (8)0.0165 (8)0.0171 (8)0.0006 (7)0.0007 (7)0.0004 (6)
C410.0198 (8)0.0143 (8)0.0231 (9)0.0020 (7)0.0017 (7)0.0024 (7)
C420.0258 (10)0.0259 (9)0.0181 (9)0.0016 (8)0.0012 (7)0.0014 (7)
C430.0224 (9)0.0275 (10)0.0234 (9)0.0004 (8)0.0036 (7)0.0023 (8)
C440.0226 (9)0.0193 (9)0.0259 (9)0.0022 (7)0.0030 (8)0.0002 (7)
C450.0271 (10)0.0236 (9)0.0205 (9)0.0018 (8)0.0037 (7)0.0028 (7)
C460.0233 (9)0.0185 (8)0.0207 (9)0.0013 (7)0.0036 (7)0.0003 (7)
C470.0249 (10)0.0319 (11)0.0333 (11)0.0027 (8)0.0026 (8)0.0005 (9)
C480.0250 (9)0.0168 (9)0.0298 (10)0.0007 (7)0.0036 (8)0.0053 (7)
O10.0247 (7)0.0170 (6)0.0248 (7)0.0018 (5)0.0028 (5)0.0012 (5)
Geometric parameters (Å, º) top
N1—C7A1.352 (2)C42—C431.388 (3)
N1—N21.379 (2)C42—H420.95
N1—H10.86C43—C441.387 (3)
N2—C31.320 (2)C43—H430.95
N4—C41.353 (2)C44—C451.400 (3)
N4—C411.433 (2)C44—C471.504 (3)
N4—C481.462 (2)C45—C461.384 (2)
N5—C41.346 (2)C45—H450.95
N5—C61.363 (2)C46—H460.95
N6—C61.345 (2)C47—H47A0.98
N6—H6B0.86C47—H47B0.9801
N6—H6A0.86C47—H47C0.98
N7—C61.343 (2)C47—H47D0.9801
N7—C7A1.347 (2)C47—H47E0.98
C3—C3A1.418 (2)C47—H47F0.98
C3—H30.95C48—H48A0.98
C3A—C7A1.400 (2)C48—H48B0.98
C3A—C41.428 (2)C48—H48C0.98
C41—C421.386 (2)O1—H1A0.82
C41—C461.388 (2)O1—H1B0.82
C7A—N1—N2111.30 (14)C43—C44—C47120.93 (17)
C7A—N1—H1130.2C45—C44—C47120.93 (17)
N2—N1—H1118.5C46—C45—C44121.16 (17)
C3—N2—N1105.81 (14)C46—C45—H45119.4
C4—N4—C41121.67 (14)C44—C45—H45119.4
C4—N4—C48121.52 (14)C45—C46—C41119.75 (16)
C41—N4—C48116.79 (14)C45—C46—H46120.1
C4—N5—C6118.94 (14)C41—C46—H46120.1
C6—N6—H6B119.9C44—C47—H47A109.5
C6—N6—H6A121.0C44—C47—H47B109.5
H6B—N6—H6A118.7H47A—C47—H47B109.5
C6—N7—C7A111.70 (14)C44—C47—H47C109.5
N2—C3—C3A111.37 (15)H47A—C47—H47C109.5
N2—C3—H3124.3H47B—C47—H47C109.5
C3A—C3—H3124.3C44—C47—H47D109.5
C7A—C3A—C3104.56 (15)H47A—C47—H47D141.1
C7A—C3A—C4114.63 (15)H47B—C47—H47D56.3
C3—C3A—C4140.78 (16)H47C—C47—H47D56.2
N5—C4—N4117.18 (15)C44—C47—H47E109.5
N5—C4—C3A119.18 (15)H47A—C47—H47E56.3
N4—C4—C3A123.60 (15)H47B—C47—H47E141.1
N7—C6—N6116.83 (15)H47C—C47—H47E56.3
N7—C6—N5127.30 (16)H47D—C47—H47E109.5
N6—C6—N5115.88 (15)C44—C47—H47F109.5
N7—C7A—N1125.27 (15)H47A—C47—H47F56.2
N7—C7A—C3A127.77 (15)H47B—C47—H47F56.3
N1—C7A—C3A106.96 (15)H47C—C47—H47F141.1
C42—C41—C46119.78 (16)H47D—C47—H47F109.5
C42—C41—N4120.15 (16)H47E—C47—H47F109.5
C46—C41—N4120.04 (16)N4—C48—H48A109.5
C41—C42—C43120.02 (17)N4—C48—H48B109.5
C41—C42—H42120.0H48A—C48—H48B109.5
C43—C42—H42120.0N4—C48—H48C109.5
C44—C43—C42121.06 (17)H48A—C48—H48C109.5
C44—C43—H43119.5H48B—C48—H48C109.5
C42—C43—H43119.5H1A—O1—H1B103.4
C43—C44—C45118.14 (17)
C7A—N1—N2—C30.45 (19)N2—N1—C7A—N7179.65 (15)
N1—N2—C3—C3A0.54 (19)N2—N1—C7A—C3A0.18 (19)
N2—C3—C3A—C7A0.4 (2)C3—C3A—C7A—N7179.97 (16)
N2—C3—C3A—C4178.4 (2)C4—C3A—C7A—N71.5 (3)
C6—N5—C4—N4171.45 (15)C3—C3A—C7A—N10.14 (18)
C6—N5—C4—C3A6.6 (2)C4—C3A—C7A—N1178.72 (14)
C41—N4—C4—N5170.51 (15)C4—N4—C41—C4268.7 (2)
C48—N4—C4—N57.7 (2)C48—N4—C41—C42109.56 (19)
C41—N4—C4—C3A11.6 (3)C4—N4—C41—C46113.54 (19)
C48—N4—C4—C3A170.21 (16)C48—N4—C41—C4668.2 (2)
C7A—C3A—C4—N56.8 (2)C46—C41—C42—C433.5 (3)
C3—C3A—C4—N5175.4 (2)N4—C41—C42—C43178.80 (16)
C7A—C3A—C4—N4171.10 (16)C41—C42—C43—C441.5 (3)
C3—C3A—C4—N46.7 (3)C42—C43—C44—C451.1 (3)
C7A—N7—C6—N6175.30 (15)C42—C43—C44—C47178.54 (17)
C7A—N7—C6—N54.4 (2)C43—C44—C45—C461.6 (3)
C4—N5—C6—N70.7 (3)C47—C44—C45—C46177.97 (17)
C4—N5—C6—N6179.63 (15)C44—C45—C46—C410.3 (3)
C6—N7—C7A—N1175.96 (16)C42—C41—C46—C452.9 (3)
C6—N7—C7A—C3A3.8 (2)N4—C41—C46—C45179.36 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N20.822.092.871 (2)158
O1—H1B···N5i0.822.052.858 (2)168
N1—H1···O1ii0.862.002.857 (2)176
N6—H6A···N7iii0.862.313.092 (2)150
N6—H6B···O1iv0.862.142.960 (2)160
C3—H3···Cg10.952.773.526 (2)137
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+2, z+1; (iii) x+1/2, y1/2, z; (iv) x1/2, y+3/2, z+1.
(VI) N4-Ethyl-N4-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine hemihydrate top
Crystal data top
2(C13H14N6)·H2OF(000) = 1112
Mr = 526.62Dx = 1.344 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2987 reflections
a = 17.642 (3) Åθ = 3.2–27.5°
b = 18.278 (3) ŵ = 0.09 mm1
c = 8.3034 (18) ÅT = 120 K
β = 103.512 (17)°Plate, colourless
V = 2603.4 (9) Å30.45 × 0.21 × 0.07 mm
Z = 4
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2987 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1829 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
ϕ & ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
h = 2222
Tmin = 0.966, Tmax = 0.994k = 2323
32439 measured reflectionsl = 1010
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0797P)2 + 1.7517P]
where P = (Fo2 + 2Fc2)/3
2987 reflections(Δ/σ)max < 0.001
178 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
2(C13H14N6)·H2OV = 2603.4 (9) Å3
Mr = 526.62Z = 4
Monoclinic, C2/cMo Kα radiation
a = 17.642 (3) ŵ = 0.09 mm1
b = 18.278 (3) ÅT = 120 K
c = 8.3034 (18) Å0.45 × 0.21 × 0.07 mm
β = 103.512 (17)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
2987 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
1829 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.994Rint = 0.060
32439 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 1.07Δρmax = 0.27 e Å3
2987 reflectionsΔρmin = 0.26 e Å3
178 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.30796 (10)0.20876 (9)0.1732 (2)0.0295 (4)
N20.36958 (10)0.18962 (10)0.3008 (2)0.0339 (4)
N50.11989 (9)0.12919 (9)0.30734 (19)0.0262 (4)
N60.03910 (10)0.17229 (10)0.0707 (2)0.0350 (5)
N70.16933 (9)0.19546 (9)0.1007 (2)0.0282 (4)
N40.19919 (10)0.07825 (9)0.5426 (2)0.0285 (4)
C30.33912 (12)0.15355 (12)0.4079 (3)0.0315 (5)
C3A0.25704 (11)0.14876 (11)0.3531 (2)0.0265 (4)
C40.19126 (12)0.11877 (10)0.4028 (2)0.0252 (4)
C60.11201 (12)0.16586 (11)0.1620 (2)0.0266 (5)
C7A0.24001 (11)0.18529 (10)0.2019 (2)0.0257 (4)
C410.27459 (12)0.07066 (11)0.6528 (2)0.0271 (5)
C420.30463 (12)0.12715 (11)0.7598 (2)0.0308 (5)
C430.37934 (12)0.12241 (12)0.8584 (3)0.0336 (5)
C440.42360 (13)0.06039 (12)0.8523 (3)0.0349 (5)
C450.39276 (13)0.00308 (12)0.7483 (3)0.0352 (5)
C460.31820 (12)0.00788 (11)0.6484 (3)0.0314 (5)
C470.13308 (12)0.04369 (12)0.5922 (3)0.0332 (5)
C480.11208 (14)0.08256 (15)0.7351 (3)0.0478 (6)
O10.50000.25671 (11)0.25000.0323 (5)
H10.31520.23600.09370.035*
H6A0.00130.15620.11000.042*
H6B0.02720.19350.02450.042*
H30.36840.13340.50880.038*
H20.27380.16930.76550.037*
H430.40030.16160.93030.040*
H440.47510.05710.91930.042*
H450.42290.03980.74560.042*
H460.29710.03150.57730.038*
H47A0.14640.00780.62360.040*
H47B0.08740.04360.49670.040*
H48A0.15710.08250.83020.072*
H48B0.06830.05740.76510.072*
H48C0.09720.13310.70330.072*
H1A0.46440.23180.26900.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0292 (10)0.0346 (9)0.0260 (9)0.0016 (7)0.0088 (7)0.0070 (7)
N20.0283 (10)0.0406 (11)0.0337 (10)0.0030 (8)0.0094 (8)0.0059 (8)
N50.0282 (9)0.0271 (9)0.0243 (9)0.0011 (7)0.0081 (7)0.0018 (7)
N60.0272 (10)0.0490 (11)0.0280 (9)0.0034 (8)0.0047 (8)0.0083 (8)
N70.0278 (10)0.0320 (9)0.0258 (9)0.0005 (7)0.0082 (7)0.0006 (7)
N40.0294 (9)0.0295 (9)0.0275 (9)0.0010 (7)0.0084 (7)0.0051 (7)
C30.0327 (12)0.0348 (12)0.0283 (11)0.0043 (9)0.0095 (9)0.0076 (9)
C3A0.0258 (11)0.0279 (10)0.0267 (10)0.0019 (8)0.0077 (8)0.0008 (8)
C40.0297 (11)0.0224 (10)0.0253 (10)0.0019 (8)0.0100 (9)0.0016 (8)
C60.0282 (11)0.0280 (11)0.0244 (10)0.0009 (8)0.0079 (9)0.0019 (8)
C7A0.0266 (11)0.0257 (10)0.0267 (10)0.0013 (8)0.0101 (9)0.0000 (8)
C410.0295 (11)0.0289 (10)0.0252 (10)0.0017 (8)0.0108 (8)0.0063 (8)
C420.0355 (12)0.0282 (11)0.0304 (11)0.0049 (9)0.0111 (9)0.0016 (9)
C430.0332 (12)0.0384 (12)0.0303 (11)0.0002 (9)0.0096 (10)0.0004 (9)
C440.0306 (12)0.0445 (13)0.0313 (11)0.0049 (10)0.0105 (9)0.0072 (10)
C450.0337 (12)0.0355 (12)0.0402 (12)0.0098 (9)0.0163 (10)0.0073 (10)
C460.0359 (12)0.0288 (11)0.0333 (11)0.0016 (9)0.0159 (9)0.0026 (9)
C470.0317 (12)0.0344 (12)0.0341 (11)0.0033 (9)0.0089 (9)0.0089 (9)
C480.0358 (13)0.0720 (18)0.0389 (13)0.0049 (12)0.0149 (11)0.0030 (12)
O10.0272 (11)0.0367 (12)0.0339 (12)0.0000.0091 (9)0.000
Geometric parameters (Å, º) top
N1—C7A1.346 (3)C41—C421.385 (3)
N1—N21.374 (2)C41—C461.387 (3)
N1—H10.86C42—C431.382 (3)
N2—C31.318 (3)C42—H20.95
N5—C41.335 (3)C43—C441.384 (3)
N5—C61.359 (2)C43—H430.95
N6—C61.337 (2)C44—C451.385 (3)
N6—H6A0.86C44—H440.95
N6—H6B0.86C45—C461.384 (3)
N7—C7A1.344 (3)C45—H450.95
N7—C61.347 (3)C46—H460.95
N4—C41.357 (2)C47—C481.502 (3)
N4—C411.434 (3)C47—H47A0.99
N4—C471.467 (3)C47—H47B0.99
C3—C3A1.416 (3)C48—H48A0.98
C3—H30.95C48—H48B0.98
C3A—C7A1.391 (3)C48—H48C0.98
C3A—C41.429 (3)O1—H1A0.82
C7A—N1—N2111.06 (17)C46—C41—N4120.05 (18)
C7A—N1—H1128.2C43—C42—C41120.2 (2)
N2—N1—H1120.4C43—C42—H2119.9
C3—N2—N1105.88 (17)C41—C42—H2119.9
C4—N5—C6118.95 (17)C42—C43—C44119.8 (2)
C6—N6—H6A118.9C42—C43—H43120.1
C6—N6—H6B123.8C44—C43—H43120.1
H6A—N6—H6B117.2C43—C44—C45120.0 (2)
C7A—N7—C6112.15 (17)C43—C44—H44120.0
C4—N4—C41119.56 (16)C45—C44—H44120.0
C4—N4—C47123.04 (17)C46—C45—C44120.4 (2)
C41—N4—C47117.34 (16)C46—C45—H45119.8
N2—C3—C3A111.19 (18)C44—C45—H45119.8
N2—C3—H3124.4C45—C46—C41119.5 (2)
C3A—C3—H3124.4C45—C46—H46120.3
C7A—C3A—C3104.46 (17)C41—C46—H46120.3
C7A—C3A—C4115.22 (18)N4—C47—C48112.15 (18)
C3—C3A—C4140.32 (19)N4—C47—H47A109.2
N5—C4—N4118.69 (17)C48—C47—H47A109.2
N5—C4—C3A119.39 (17)N4—C47—H47B109.2
N4—C4—C3A121.90 (18)C48—C47—H47B109.2
N6—C6—N7117.28 (18)H47A—C47—H47B107.9
N6—C6—N5115.60 (18)C47—C48—H48A109.5
N7—C6—N5127.11 (18)C47—C48—H48B109.5
N7—C7A—N1125.45 (18)H48A—C48—H48B109.5
N7—C7A—C3A127.15 (18)C47—C48—H48C109.5
N1—C7A—C3A107.41 (17)H48A—C48—H48C109.5
C42—C41—C46120.17 (19)H48B—C48—H48C109.5
C42—C41—N4119.75 (18)
C7A—N1—N2—C30.5 (2)N2—N1—C7A—N7179.92 (18)
N1—N2—C3—C3A0.3 (2)N2—N1—C7A—C3A0.5 (2)
N2—C3—C3A—C7A0.0 (2)C3—C3A—C7A—N7179.85 (19)
N2—C3—C3A—C4179.1 (2)C4—C3A—C7A—N70.5 (3)
C6—N5—C4—N4175.97 (17)C3—C3A—C7A—N10.3 (2)
C6—N5—C4—C3A2.4 (3)C4—C3A—C7A—N1179.04 (17)
C41—N4—C4—N5175.65 (17)C4—N4—C41—C4278.2 (2)
C47—N4—C4—N51.6 (3)C47—N4—C41—C4299.2 (2)
C41—N4—C4—C3A6.0 (3)C4—N4—C41—C4699.8 (2)
C47—N4—C4—C3A176.79 (19)C47—N4—C41—C4682.8 (2)
C7A—C3A—C4—N52.0 (3)C46—C41—C42—C432.4 (3)
C3—C3A—C4—N5179.0 (2)N4—C41—C42—C43175.62 (18)
C7A—C3A—C4—N4176.32 (17)C41—C42—C43—C441.2 (3)
C3—C3A—C4—N42.6 (4)C42—C43—C44—C450.5 (3)
C7A—N7—C6—N6179.54 (17)C43—C44—C45—C461.0 (3)
C7A—N7—C6—N50.1 (3)C44—C45—C46—C410.1 (3)
C4—N5—C6—N6178.06 (17)C42—C41—C46—C451.8 (3)
C4—N5—C6—N71.4 (3)N4—C41—C46—C45176.16 (18)
C6—N7—C7A—N1179.99 (18)C4—N4—C47—C48106.3 (2)
C6—N7—C7A—C3A0.5 (3)C41—N4—C47—C4871.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N20.821.912.726 (2)169
N1—H1···N7i0.862.112.971 (2)179
N6—H6A···N5ii0.862.443.293 (2)169
N6—H6B···O1i0.862.042.897 (2)179
C3—H3···Cg10.952.473.260 (3)140
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y, z+1/2.
(VII) N4-(4-Methoxyphenyl)-N4-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine hemihydrate top
Crystal data top
2(C13H14N6O)·H2OZ = 2
Mr = 558.62F(000) = 588
Triclinic, P1Dx = 1.338 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9516 (5) ÅCell parameters from 6316 reflections
b = 12.0627 (7) Åθ = 3.8–27.5°
c = 12.9053 (7) ŵ = 0.09 mm1
α = 91.612 (4)°T = 120 K
β = 92.065 (3)°Block, colourless
γ = 95.259 (5)°0.54 × 0.48 × 0.40 mm
V = 1386.06 (13) Å3
Data collection top
Bruker-Nonius KappaCCD
diffractometer
6316 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode4620 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ϕ & ω scansθmax = 27.5°, θmin = 3.8°
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
h = 1111
Tmin = 0.955, Tmax = 0.963k = 1515
31433 measured reflectionsl = 1616
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.025P)2 + 1.067P]
where P = (Fo2 + 2Fc2)/3
6316 reflections(Δ/σ)max = 0.001
374 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
2(C13H14N6O)·H2Oγ = 95.259 (5)°
Mr = 558.62V = 1386.06 (13) Å3
Triclinic, P1Z = 2
a = 8.9516 (5) ÅMo Kα radiation
b = 12.0627 (7) ŵ = 0.09 mm1
c = 12.9053 (7) ÅT = 120 K
α = 91.612 (4)°0.54 × 0.48 × 0.40 mm
β = 92.065 (3)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
6316 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
4620 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 0.963Rint = 0.030
31433 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.104H-atom parameters constrained
S = 1.11Δρmax = 0.26 e Å3
6316 reflectionsΔρmin = 0.28 e Å3
374 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O140.88960 (14)0.39539 (11)0.50974 (10)0.0277 (3)
N110.16054 (15)0.09692 (11)0.51768 (10)0.0165 (3)
N120.28222 (15)0.16483 (12)0.55742 (11)0.0194 (3)
N140.50386 (16)0.10912 (12)0.25573 (11)0.0207 (3)
N150.28424 (15)0.00678 (12)0.23784 (11)0.0175 (3)
N160.06661 (16)0.11967 (12)0.21153 (11)0.0226 (3)
N170.09054 (15)0.01625 (11)0.36478 (10)0.0154 (3)
C130.38265 (19)0.16706 (14)0.48484 (13)0.0186 (3)
C13A0.33003 (18)0.09931 (13)0.39713 (12)0.0159 (3)
C140.37451 (18)0.06679 (13)0.29634 (12)0.0156 (3)
C160.14874 (18)0.04505 (13)0.27428 (12)0.0156 (3)
C17A0.18695 (17)0.05532 (13)0.42286 (12)0.0141 (3)
C1410.60971 (18)0.18074 (14)0.31848 (13)0.0177 (3)
C1420.69949 (19)0.13607 (15)0.39270 (14)0.0215 (4)
C1430.79459 (19)0.20513 (15)0.45956 (14)0.0220 (4)
C1440.80066 (18)0.31966 (14)0.44965 (14)0.0201 (4)
C1450.71228 (19)0.36431 (15)0.37339 (14)0.0219 (4)
C1460.61742 (19)0.29567 (15)0.30807 (14)0.0208 (4)
C1470.9706 (2)0.35624 (18)0.59598 (15)0.0319 (5)
C1480.5426 (2)0.0818 (2)0.14961 (15)0.0386 (5)
O240.36346 (14)0.52229 (11)0.60950 (10)0.0264 (3)
N210.34896 (15)0.48485 (12)0.90715 (11)0.0182 (3)
N220.23389 (16)0.44450 (12)0.83850 (11)0.0215 (3)
C230.1348 (2)0.51917 (15)0.84109 (13)0.0208 (4)
N240.00986 (16)0.75434 (12)0.91269 (11)0.0191 (3)
N260.42071 (17)0.79306 (13)1.13795 (12)0.0250 (3)
N270.40754 (15)0.63965 (11)1.02714 (10)0.0168 (3)
C27A0.31927 (18)0.58162 (13)0.95342 (12)0.0154 (3)
C23A0.18130 (18)0.60842 (14)0.91216 (12)0.0165 (3)
C240.13336 (18)0.71065 (14)0.95126 (12)0.0159 (3)
N250.21448 (15)0.76827 (11)1.02738 (10)0.0170 (3)
C260.34639 (18)0.73114 (14)1.06149 (12)0.0167 (3)
C2410.08765 (18)0.69347 (14)0.83610 (13)0.0180 (3)
C2420.18882 (19)0.60792 (16)0.86520 (13)0.0229 (4)
C2430.28168 (19)0.54638 (16)0.79153 (14)0.0238 (4)
C2440.27389 (18)0.57398 (15)0.68797 (13)0.0200 (4)
C2450.17221 (19)0.66035 (15)0.65863 (13)0.0211 (4)
C2460.07945 (19)0.71990 (15)0.73215 (13)0.0207 (4)
C2470.4570 (2)0.42474 (16)0.63362 (17)0.0315 (4)
C2480.0328 (2)0.86190 (16)0.95045 (16)0.0322 (5)
O10.25840 (13)0.21899 (10)0.77303 (9)0.0229 (3)
H110.08770.07610.55650.020*
H16B0.02380.14410.22470.027*
H16A0.10490.14120.15510.027*
H130.47800.20880.49070.022*
H1420.69640.05750.39820.026*
H1430.85470.17410.51140.026*
H1450.71740.44270.36630.026*
H1460.55750.32660.25610.025*
H14A0.90010.31860.64290.048*
H14B1.02760.41940.63310.048*
H14C1.03980.30370.57150.048*
H14D0.60260.01780.14970.058*
H14E0.60080.14600.12110.058*
H14F0.45050.06340.10690.058*
H210.42040.44470.92340.022*
H230.04380.51370.80040.025*
H26B0.51060.78191.15810.030*
H26A0.38510.85341.15850.030*
H2420.19520.59080.93640.027*
H2430.34950.48630.81180.029*
H2450.16660.67850.58760.025*
H2460.01010.77890.71180.025*
H24A0.52550.44330.68770.047*
H24B0.39430.36770.65850.047*
H24C0.51540.39620.57120.047*
H24D0.05780.91160.96830.048*
H24E0.09260.85121.01220.048*
H24F0.09240.89500.89620.048*
H1B0.24770.28530.78270.034*
H1A0.27010.21310.71040.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O140.0229 (7)0.0232 (7)0.0356 (8)0.0003 (5)0.0051 (6)0.0048 (6)
N110.0137 (6)0.0190 (7)0.0162 (7)0.0006 (5)0.0019 (5)0.0037 (6)
N120.0171 (7)0.0192 (7)0.0210 (7)0.0004 (6)0.0002 (6)0.0046 (6)
N140.0186 (7)0.0248 (8)0.0177 (7)0.0041 (6)0.0048 (6)0.0021 (6)
N150.0160 (7)0.0198 (7)0.0165 (7)0.0004 (6)0.0019 (5)0.0019 (6)
N160.0182 (7)0.0291 (8)0.0187 (7)0.0054 (6)0.0039 (6)0.0081 (6)
N170.0148 (7)0.0163 (7)0.0146 (7)0.0005 (5)0.0008 (5)0.0012 (5)
C130.0169 (8)0.0185 (8)0.0201 (8)0.0005 (7)0.0021 (7)0.0030 (7)
C13A0.0156 (8)0.0149 (8)0.0171 (8)0.0009 (6)0.0008 (6)0.0004 (6)
C140.0155 (8)0.0141 (8)0.0174 (8)0.0014 (6)0.0016 (6)0.0017 (6)
C160.0167 (8)0.0156 (8)0.0146 (8)0.0020 (6)0.0001 (6)0.0009 (6)
C17A0.0143 (7)0.0136 (8)0.0146 (8)0.0028 (6)0.0005 (6)0.0003 (6)
C1410.0144 (8)0.0196 (9)0.0190 (8)0.0010 (6)0.0053 (6)0.0006 (7)
C1420.0195 (8)0.0178 (9)0.0274 (9)0.0017 (7)0.0037 (7)0.0028 (7)
C1430.0166 (8)0.0229 (9)0.0267 (9)0.0034 (7)0.0016 (7)0.0044 (7)
C1440.0136 (8)0.0203 (9)0.0259 (9)0.0008 (7)0.0033 (7)0.0032 (7)
C1450.0208 (9)0.0154 (8)0.0299 (10)0.0020 (7)0.0025 (7)0.0030 (7)
C1460.0182 (8)0.0229 (9)0.0219 (9)0.0036 (7)0.0026 (7)0.0046 (7)
C1470.0280 (10)0.0379 (12)0.0290 (10)0.0023 (9)0.0039 (8)0.0058 (9)
C1480.0375 (12)0.0513 (14)0.0237 (10)0.0165 (10)0.0161 (9)0.0090 (9)
O240.0225 (6)0.0321 (7)0.0235 (7)0.0007 (5)0.0050 (5)0.0056 (6)
N210.0164 (7)0.0190 (7)0.0194 (7)0.0042 (6)0.0011 (6)0.0041 (6)
N220.0222 (7)0.0223 (8)0.0200 (7)0.0042 (6)0.0012 (6)0.0061 (6)
C230.0215 (9)0.0217 (9)0.0195 (8)0.0049 (7)0.0013 (7)0.0031 (7)
N240.0219 (7)0.0175 (7)0.0184 (7)0.0066 (6)0.0035 (6)0.0027 (6)
N260.0216 (8)0.0239 (8)0.0294 (8)0.0088 (6)0.0088 (6)0.0120 (7)
N270.0172 (7)0.0161 (7)0.0170 (7)0.0025 (6)0.0000 (6)0.0019 (6)
C27A0.0175 (8)0.0142 (8)0.0151 (8)0.0026 (6)0.0043 (6)0.0012 (6)
C23A0.0189 (8)0.0177 (8)0.0129 (8)0.0020 (7)0.0006 (6)0.0007 (6)
C240.0171 (8)0.0166 (8)0.0142 (8)0.0010 (6)0.0023 (6)0.0020 (6)
N250.0179 (7)0.0164 (7)0.0168 (7)0.0032 (6)0.0003 (6)0.0016 (6)
C260.0183 (8)0.0159 (8)0.0160 (8)0.0016 (6)0.0016 (6)0.0003 (6)
C2410.0182 (8)0.0187 (8)0.0180 (8)0.0078 (7)0.0017 (7)0.0014 (7)
C2420.0219 (9)0.0310 (10)0.0165 (8)0.0042 (8)0.0030 (7)0.0043 (7)
C2430.0192 (9)0.0270 (10)0.0251 (9)0.0001 (7)0.0016 (7)0.0048 (8)
C2440.0153 (8)0.0240 (9)0.0211 (9)0.0062 (7)0.0016 (7)0.0036 (7)
C2450.0233 (9)0.0259 (9)0.0150 (8)0.0060 (7)0.0011 (7)0.0031 (7)
C2460.0215 (9)0.0207 (9)0.0203 (9)0.0033 (7)0.0008 (7)0.0032 (7)
C2470.0257 (10)0.0267 (10)0.0408 (12)0.0005 (8)0.0049 (9)0.0070 (9)
C2480.0386 (11)0.0268 (10)0.0323 (11)0.0182 (9)0.0136 (9)0.0100 (8)
O10.0270 (7)0.0204 (6)0.0209 (6)0.0027 (5)0.0001 (5)0.0055 (5)
Geometric parameters (Å, º) top
O14—C1441.361 (2)O24—C2471.429 (2)
O14—C1471.422 (2)N21—C27A1.349 (2)
N11—C17A1.347 (2)N21—N221.379 (2)
N11—N121.3759 (19)N21—H210.86
N11—H110.86N22—C231.321 (2)
N12—C131.321 (2)C23—C23A1.417 (2)
N14—C141.351 (2)C23—H230.95
N14—C1411.434 (2)N24—C241.353 (2)
N14—C1481.461 (2)N24—C2411.434 (2)
N15—C141.341 (2)N24—C2481.461 (2)
N15—C161.362 (2)N26—C261.340 (2)
N16—C161.342 (2)N26—H26B0.86
N16—H16B0.86N26—H26A0.86
N16—H16A0.86N27—C261.347 (2)
N17—C161.345 (2)N27—C27A1.351 (2)
N17—C17A1.354 (2)C27A—C23A1.396 (2)
C13—C13A1.418 (2)C23A—C241.427 (2)
C13—H130.95C24—N251.339 (2)
C13A—C17A1.396 (2)N25—C261.364 (2)
C13A—C141.429 (2)C241—C2421.379 (2)
C141—C1421.381 (2)C241—C2461.390 (2)
C141—C1461.392 (2)C242—C2431.392 (3)
C142—C1431.393 (2)C242—H2420.95
C142—H1420.95C243—C2441.389 (2)
C143—C1441.387 (2)C243—H2430.95
C143—H1430.95C244—C2451.389 (2)
C144—C1451.391 (2)C245—C2461.379 (2)
C145—C1461.377 (3)C245—H2450.95
C145—H1450.95C246—H2460.95
C146—H1460.95C247—H24A0.98
C147—H14A0.98C247—H24B0.98
C147—H14B0.98C247—H24C0.98
C147—H14C0.98C248—H24D0.98
C148—H14D0.98C248—H24E0.98
C148—H14E0.98C248—H24F0.98
C148—H14F0.98O1—H1B0.82
O24—C2441.368 (2)O1—H1A0.82
C144—O14—C147118.13 (15)C27A—N21—N22111.26 (13)
C17A—N11—N12111.18 (13)C27A—N21—H21127.2
C17A—N11—H11127.2N22—N21—H21120.7
N12—N11—H11120.5C23—N22—N21105.50 (14)
C13—N12—N11105.72 (13)N22—C23—C23A111.60 (15)
C14—N14—C141119.81 (14)N22—C23—H23124.2
C14—N14—C148122.08 (15)C23A—C23—H23124.2
C141—N14—C148118.09 (14)C24—N24—C241120.58 (14)
C14—N15—C16118.96 (14)C24—N24—C248121.65 (14)
C16—N16—H16B122.1C241—N24—C248117.72 (14)
C16—N16—H16A118.4C26—N26—H26B121.8
H16B—N16—H16A119.4C26—N26—H26A118.5
C16—N17—C17A111.97 (13)H26B—N26—H26A118.5
N12—C13—C13A111.40 (15)C26—N27—C27A112.10 (14)
N12—C13—H13124.3N21—C27A—N27125.44 (15)
C13A—C13—H13124.3N21—C27A—C23A107.34 (14)
C17A—C13A—C13104.23 (14)N27—C27A—C23A127.21 (15)
C17A—C13A—C14114.94 (14)C27A—C23A—C23104.28 (14)
C13—C13A—C14140.80 (15)C27A—C23A—C24114.94 (15)
N15—C14—N14117.87 (14)C23—C23A—C24140.78 (16)
N15—C14—C13A119.52 (14)N25—C24—N24117.73 (15)
N14—C14—C13A122.59 (15)N25—C24—C23A119.62 (15)
N16—C16—N17117.79 (15)N24—C24—C23A122.63 (15)
N16—C16—N15115.03 (14)C24—N25—C26118.95 (14)
N17—C16—N15127.18 (15)N26—C26—N27117.62 (15)
N11—C17A—N17125.30 (14)N26—C26—N25115.37 (15)
N11—C17A—C13A107.44 (14)N27—C26—N25127.01 (15)
N17—C17A—C13A127.26 (15)C242—C241—C246119.81 (16)
C142—C141—C146119.85 (16)C242—C241—N24120.10 (15)
C142—C141—N14119.93 (16)C246—C241—N24120.09 (16)
C146—C141—N14120.16 (15)C241—C242—C243120.78 (16)
C141—C142—C143120.59 (16)C241—C242—H242119.6
C141—C142—H142119.7C243—C242—H242119.6
C143—C142—H142119.7C244—C243—C242119.07 (17)
C144—C143—C142119.33 (16)C244—C243—H243120.5
C144—C143—H143120.3C242—C243—H243120.5
C142—C143—H143120.3O24—C244—C243124.21 (16)
O14—C144—C143124.75 (16)O24—C244—C245115.63 (15)
O14—C144—C145115.33 (16)C243—C244—C245120.15 (16)
C143—C144—C145119.92 (16)C246—C245—C244120.27 (16)
C146—C145—C144120.51 (16)C246—C245—H245119.9
C146—C145—H145119.7C244—C245—H245119.9
C144—C145—H145119.7C245—C246—C241119.90 (16)
C145—C146—C141119.78 (16)C245—C246—H246120.1
C145—C146—H146120.1C241—C246—H246120.1
C141—C146—H146120.1O24—C247—H24A109.5
O14—C147—H14A109.5O24—C247—H24B109.5
O14—C147—H14B109.5H24A—C247—H24B109.5
H14A—C147—H14B109.5O24—C247—H24C109.5
O14—C147—H14C109.5H24A—C247—H24C109.5
H14A—C147—H14C109.5H24B—C247—H24C109.5
H14B—C147—H14C109.5N24—C248—H24D109.5
N14—C148—H14D109.5N24—C248—H24E109.5
N14—C148—H14E109.5H24D—C248—H24E109.5
H14D—C148—H14E109.5N24—C248—H24F109.5
N14—C148—H14F109.5H24D—C248—H24F109.5
H14D—C148—H14F109.5H24E—C248—H24F109.5
H14E—C148—H14F109.5H1B—O1—H1A103.8
C244—O24—C247117.61 (15)
C17A—N11—N12—C131.62 (18)C27A—N21—N22—C231.61 (19)
N11—N12—C13—C13A1.04 (19)N21—N22—C23—C23A0.96 (19)
N12—C13—C13A—C17A0.14 (19)N22—N21—C27A—N27177.49 (15)
N12—C13—C13A—C14178.2 (2)N22—N21—C27A—C23A1.62 (18)
C16—N15—C14—N14175.71 (15)C26—N27—C27A—N21177.82 (16)
C16—N15—C14—C13A2.9 (2)C26—N27—C27A—C23A1.1 (2)
C141—N14—C14—N15174.76 (15)N21—C27A—C23A—C230.96 (18)
C148—N14—C14—N153.4 (3)N27—C27A—C23A—C23178.13 (16)
C141—N14—C14—C13A6.6 (2)N21—C27A—C23A—C24178.77 (14)
C148—N14—C14—C13A175.14 (18)N27—C27A—C23A—C242.1 (2)
C17A—C13A—C14—N154.3 (2)N22—C23—C23A—C27A0.0 (2)
C13—C13A—C14—N15177.8 (2)N22—C23—C23A—C24179.6 (2)
C17A—C13A—C14—N14174.26 (15)C241—N24—C24—N25175.73 (15)
C13—C13A—C14—N143.7 (3)C248—N24—C24—N251.4 (2)
C17A—N17—C16—N16177.10 (15)C241—N24—C24—C23A6.0 (2)
C17A—N17—C16—N152.8 (2)C248—N24—C24—C23A176.88 (17)
C14—N15—C16—N16179.02 (15)C27A—C23A—C24—N254.7 (2)
C14—N15—C16—N170.9 (3)C23—C23A—C24—N25175.7 (2)
N12—N11—C17A—N17178.29 (15)C27A—C23A—C24—N24173.57 (15)
N12—N11—C17A—C13A1.56 (18)C23—C23A—C24—N246.0 (3)
C16—N17—C17A—N11178.81 (15)N24—C24—N25—C26174.38 (14)
C16—N17—C17A—C13A1.0 (2)C23A—C24—N25—C264.0 (2)
C13—C13A—C17A—N110.85 (18)C27A—N27—C26—N26177.27 (15)
C14—C13A—C17A—N11177.78 (14)C27A—N27—C26—N252.2 (2)
C13—C13A—C17A—N17178.99 (16)C24—N25—C26—N26179.80 (15)
C14—C13A—C17A—N172.4 (2)C24—N25—C26—N270.4 (3)
C14—N14—C141—C14276.1 (2)C24—N24—C241—C24278.1 (2)
C148—N14—C141—C142102.1 (2)C248—N24—C241—C24299.2 (2)
C14—N14—C141—C146100.91 (19)C24—N24—C241—C246101.36 (19)
C148—N14—C141—C14680.8 (2)C248—N24—C241—C24681.4 (2)
C146—C141—C142—C1432.0 (3)C246—C241—C242—C2430.9 (3)
N14—C141—C142—C143175.07 (15)N24—C241—C242—C243178.48 (16)
C141—C142—C143—C1441.3 (3)C241—C242—C243—C2441.6 (3)
C147—O14—C144—C1437.0 (2)C247—O24—C244—C2438.5 (2)
C147—O14—C144—C145173.43 (16)C247—O24—C244—C245172.70 (15)
C142—C143—C144—O14179.56 (16)C242—C243—C244—O24177.39 (16)
C142—C143—C144—C1450.0 (3)C242—C243—C244—C2451.4 (3)
O14—C144—C145—C146179.81 (16)O24—C244—C245—C246178.26 (15)
C143—C144—C145—C1460.6 (3)C243—C244—C245—C2460.6 (3)
C144—C145—C146—C1410.1 (3)C244—C245—C246—C2410.0 (3)
C142—C141—C146—C1451.4 (2)C242—C241—C246—C2450.1 (3)
N14—C141—C146—C145175.66 (15)N24—C241—C246—C245179.27 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N120.822.052.860 (2)168
O1—H1B···N220.822.052.856 (2)168
N11—H11···N17i0.862.012.868 (2)174
N21—H21···N27ii0.862.022.875 (2)175
N16—H16A···N25iii0.862.253.099 (2)167
N26—H26A···N15iv0.862.233.076 (2)170
N16—H16B···O1i0.862.213.059 (2)169
N26—H26B···O1ii0.862.223.073 (2)170
C13—H13···Cg20.952.523.300 (2)139
C23—H23···Cg30.952.623.393 (2)139
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+2; (iii) x, y1, z1; (iv) x, y+1, z+1.
(VIII) N4-Benzyl-N4-phenylyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine monohydrate top
Crystal data top
C18H16N6·H2OF(000) = 1408
Mr = 334.38Dx = 1.362 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7493 reflections
a = 10.1880 (11) Åθ = 3.0–27.5°
b = 9.5136 (10) ŵ = 0.09 mm1
c = 33.695 (4) ÅT = 120 K
β = 93.131 (7)°Block, colourless
V = 3261.0 (6) Å30.44 × 0.33 × 0.24 mm
Z = 8
Data collection top
Bruker-Nonius KappaCCD
diffractometer
7493 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode3887 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.095
ϕ & ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
h = 1313
Tmin = 0.968, Tmax = 0.979k = 1212
83278 measured reflectionsl = 4343
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.220H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.1085P)2 + 1.9398P]
where P = (Fo2 + 2Fc2)/3
7493 reflections(Δ/σ)max < 0.001
451 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C18H16N6·H2OV = 3261.0 (6) Å3
Mr = 334.38Z = 8
Monoclinic, P21/nMo Kα radiation
a = 10.1880 (11) ŵ = 0.09 mm1
b = 9.5136 (10) ÅT = 120 K
c = 33.695 (4) Å0.44 × 0.33 × 0.24 mm
β = 93.131 (7)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
7493 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
3887 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.979Rint = 0.095
83278 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.220H-atom parameters constrained
S = 1.04Δρmax = 0.42 e Å3
7493 reflectionsΔρmin = 0.33 e Å3
451 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.4954 (2)0.3661 (3)0.66767 (7)0.0281 (6)
N120.4359 (2)0.3813 (3)0.70291 (7)0.0294 (6)
N140.8322 (2)0.4853 (3)0.75854 (7)0.0263 (5)
N150.8722 (2)0.4543 (2)0.69310 (7)0.0260 (5)
N160.9199 (2)0.4348 (3)0.62837 (7)0.0323 (6)
N170.7076 (2)0.3894 (2)0.64284 (7)0.0264 (5)
C130.5304 (3)0.4151 (3)0.72940 (8)0.0285 (7)
C13A0.6531 (3)0.4201 (3)0.71188 (8)0.0261 (6)
C140.7865 (3)0.4533 (3)0.72154 (8)0.0245 (6)
C160.8296 (3)0.4254 (3)0.65569 (8)0.0269 (6)
C17A0.6242 (3)0.3907 (3)0.67209 (8)0.0248 (6)
C1410.7546 (3)0.4620 (3)0.79197 (8)0.0268 (6)
C1420.7339 (3)0.3267 (3)0.80463 (9)0.0317 (7)
C1430.6594 (3)0.3043 (4)0.83683 (9)0.0350 (7)
C1440.6076 (3)0.4164 (4)0.85628 (9)0.0372 (8)
C1450.6299 (3)0.5500 (4)0.84353 (10)0.0409 (8)
C1460.7025 (3)0.5728 (3)0.81116 (9)0.0337 (7)
C1470.9603 (3)0.5512 (3)0.76613 (9)0.0285 (7)
C1511.0688 (3)0.4536 (3)0.78000 (8)0.0293 (7)
C1521.0724 (3)0.3144 (3)0.76936 (9)0.0339 (7)
C1531.1775 (3)0.2314 (4)0.78229 (10)0.0395 (8)
C1541.2785 (3)0.2859 (4)0.80574 (11)0.0462 (9)
C1551.2751 (3)0.4247 (4)0.81655 (11)0.0492 (9)
C1561.1709 (3)0.5083 (4)0.80370 (10)0.0386 (8)
O10.1674 (2)0.3991 (3)0.67914 (6)0.0438 (6)
N210.5882 (2)0.3153 (3)0.56803 (7)0.0304 (6)
N220.6494 (2)0.3007 (3)0.53336 (7)0.0358 (6)
N240.2621 (2)0.1649 (3)0.47681 (7)0.0287 (6)
N250.2161 (2)0.2095 (3)0.54118 (7)0.0282 (6)
N260.1620 (2)0.2353 (3)0.60504 (7)0.0325 (6)
N270.3745 (2)0.2858 (3)0.59207 (7)0.0279 (6)
C230.5578 (3)0.2608 (3)0.50660 (9)0.0336 (7)
C23A0.4347 (3)0.2506 (3)0.52338 (8)0.0282 (7)
C240.3035 (3)0.2088 (3)0.51343 (8)0.0280 (7)
C260.2548 (3)0.2452 (3)0.57856 (8)0.0275 (7)
C27A0.4597 (3)0.2850 (3)0.56293 (8)0.0270 (6)
C2410.3425 (3)0.1765 (3)0.44351 (8)0.0295 (7)
C2420.3712 (3)0.3066 (3)0.42853 (9)0.0322 (7)
C2430.4477 (3)0.3159 (4)0.39610 (9)0.0359 (8)
C2440.4918 (3)0.1968 (4)0.37829 (9)0.0387 (8)
C2450.4616 (3)0.0669 (4)0.39340 (9)0.0384 (8)
C2460.3870 (3)0.0571 (3)0.42601 (9)0.0340 (7)
C2470.1347 (3)0.0982 (3)0.47029 (9)0.0327 (7)
C2510.0235 (3)0.1936 (3)0.45735 (8)0.0292 (7)
C2520.0296 (3)0.3375 (3)0.46150 (9)0.0346 (7)
C2530.0782 (3)0.4204 (4)0.44958 (9)0.0405 (8)
C2540.1897 (3)0.3589 (4)0.43346 (10)0.0446 (9)
C2550.1956 (3)0.2159 (4)0.42920 (10)0.0446 (9)
C2560.0905 (3)0.1341 (4)0.44097 (9)0.0341 (7)
O20.9139 (2)0.2560 (2)0.55334 (6)0.0386 (6)
H110.44760.33460.64320.034*
H16A0.90590.40110.60100.039*
H16B1.00820.45680.63970.039*
H130.51780.43360.75660.034*
H1420.77080.24940.79130.038*
H1430.64360.21130.84560.042*
H1440.55640.40110.87860.045*
H1450.59470.62760.85720.049*
H1460.71650.66590.80210.040*
H14A0.95180.62530.78640.034*
H14B0.98570.59760.74140.034*
H1521.00260.27510.75310.041*
H1531.17950.13520.77480.047*
H1541.35050.22810.81450.055*
H1551.34490.46340.83290.059*
H1561.16940.60450.81130.046*
H1A0.25050.39060.69500.066*
H1B0.10620.39230.70050.066*
H210.63670.34410.59260.037*
H26A0.17680.27350.63190.039*
H26B0.07260.22150.59350.039*
H230.57290.24140.47960.040*
H2420.33870.38930.44040.039*
H2430.47000.40560.38610.043*
H2440.54290.20370.35560.046*
H2450.49240.01600.38120.046*
H2460.36630.03250.43640.041*
H24A0.11230.05130.49530.039*
H24B0.14220.02420.44990.039*
H2520.10750.38040.47250.042*
H2530.07400.51950.45270.049*
H2540.26320.41520.42520.053*
H2550.27340.17320.41800.054*
H2560.09590.03500.43780.041*
H2A0.82810.27890.54040.058*
H2B0.97040.25390.53070.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0230 (13)0.0404 (15)0.0208 (12)0.0016 (11)0.0006 (10)0.0009 (11)
N120.0252 (13)0.0365 (14)0.0264 (13)0.0026 (11)0.0011 (10)0.0009 (11)
N140.0231 (12)0.0340 (14)0.0216 (12)0.0037 (10)0.0018 (10)0.0018 (10)
N150.0243 (12)0.0297 (13)0.0241 (12)0.0035 (10)0.0007 (10)0.0011 (10)
N160.0267 (13)0.0457 (16)0.0244 (13)0.0010 (11)0.0005 (10)0.0045 (11)
N170.0231 (13)0.0320 (14)0.0238 (12)0.0020 (10)0.0001 (10)0.0001 (10)
C130.0281 (16)0.0321 (17)0.0250 (15)0.0027 (13)0.0007 (12)0.0000 (12)
C13A0.0279 (16)0.0261 (15)0.0242 (15)0.0012 (12)0.0008 (12)0.0010 (12)
C140.0233 (15)0.0246 (15)0.0255 (15)0.0004 (12)0.0002 (12)0.0003 (12)
C160.0256 (15)0.0278 (16)0.0272 (15)0.0025 (12)0.0011 (12)0.0009 (12)
C17A0.0222 (15)0.0278 (15)0.0240 (14)0.0010 (12)0.0017 (11)0.0003 (12)
C1410.0219 (14)0.0359 (17)0.0221 (14)0.0011 (13)0.0026 (11)0.0016 (12)
C1420.0330 (17)0.0300 (17)0.0317 (17)0.0009 (13)0.0015 (13)0.0021 (13)
C1430.0318 (17)0.0413 (19)0.0317 (17)0.0044 (14)0.0008 (13)0.0091 (14)
C1440.0308 (17)0.055 (2)0.0255 (16)0.0074 (15)0.0018 (13)0.0025 (15)
C1450.0402 (19)0.045 (2)0.0384 (19)0.0028 (16)0.0088 (15)0.0123 (16)
C1460.0321 (17)0.0335 (18)0.0357 (17)0.0018 (13)0.0038 (14)0.0050 (14)
C1470.0270 (16)0.0317 (16)0.0265 (15)0.0048 (13)0.0013 (12)0.0024 (12)
C1510.0252 (15)0.0384 (18)0.0245 (15)0.0023 (13)0.0027 (12)0.0012 (13)
C1520.0320 (17)0.0369 (18)0.0327 (17)0.0023 (14)0.0009 (13)0.0012 (14)
C1530.0361 (18)0.0370 (19)0.0457 (19)0.0035 (15)0.0041 (15)0.0013 (15)
C1540.0290 (18)0.052 (2)0.057 (2)0.0054 (16)0.0034 (16)0.0027 (18)
C1550.0306 (18)0.053 (2)0.062 (2)0.0021 (16)0.0142 (17)0.0024 (18)
C1560.0295 (17)0.0391 (19)0.0466 (19)0.0018 (14)0.0045 (14)0.0051 (15)
O10.0277 (12)0.0718 (17)0.0319 (12)0.0007 (11)0.0014 (9)0.0089 (11)
N210.0248 (13)0.0456 (16)0.0207 (12)0.0028 (11)0.0003 (10)0.0023 (11)
N220.0295 (14)0.0528 (17)0.0250 (13)0.0029 (12)0.0018 (11)0.0024 (12)
N240.0263 (13)0.0365 (15)0.0230 (13)0.0027 (11)0.0003 (10)0.0025 (10)
N250.0259 (13)0.0350 (14)0.0235 (12)0.0001 (11)0.0004 (10)0.0013 (10)
N260.0235 (13)0.0510 (17)0.0232 (13)0.0005 (11)0.0031 (10)0.0038 (11)
N270.0220 (13)0.0381 (15)0.0235 (12)0.0021 (11)0.0004 (10)0.0015 (11)
C230.0300 (16)0.049 (2)0.0215 (15)0.0010 (14)0.0007 (13)0.0014 (14)
C23A0.0246 (15)0.0375 (17)0.0222 (14)0.0004 (13)0.0010 (12)0.0006 (12)
C240.0283 (16)0.0314 (16)0.0241 (15)0.0003 (12)0.0001 (12)0.0004 (12)
C260.0269 (16)0.0296 (16)0.0255 (15)0.0022 (12)0.0021 (12)0.0005 (12)
C27A0.0257 (15)0.0302 (16)0.0248 (15)0.0001 (12)0.0016 (12)0.0004 (12)
C2410.0264 (16)0.0403 (18)0.0214 (15)0.0006 (13)0.0036 (12)0.0030 (13)
C2420.0317 (17)0.0362 (18)0.0283 (16)0.0030 (14)0.0033 (13)0.0028 (13)
C2430.0313 (17)0.045 (2)0.0313 (17)0.0053 (15)0.0013 (14)0.0099 (14)
C2440.0315 (17)0.058 (2)0.0263 (16)0.0032 (16)0.0002 (13)0.0009 (15)
C2450.0317 (17)0.046 (2)0.0376 (18)0.0062 (15)0.0006 (14)0.0079 (15)
C2460.0313 (17)0.0365 (18)0.0339 (17)0.0031 (14)0.0008 (14)0.0030 (14)
C2470.0309 (17)0.0379 (18)0.0290 (16)0.0084 (14)0.0028 (13)0.0014 (13)
C2510.0246 (15)0.0419 (19)0.0212 (14)0.0031 (13)0.0009 (12)0.0012 (13)
C2520.0328 (17)0.0431 (19)0.0279 (16)0.0066 (14)0.0015 (13)0.0011 (14)
C2530.0386 (19)0.044 (2)0.0392 (19)0.0017 (15)0.0021 (15)0.0087 (15)
C2540.0299 (18)0.058 (2)0.046 (2)0.0074 (16)0.0011 (15)0.0038 (17)
C2550.0276 (18)0.063 (3)0.043 (2)0.0032 (16)0.0000 (15)0.0009 (17)
C2560.0284 (17)0.0445 (19)0.0294 (16)0.0075 (14)0.0003 (13)0.0023 (14)
O20.0288 (12)0.0552 (15)0.0319 (12)0.0015 (10)0.0026 (9)0.0043 (10)
Geometric parameters (Å, º) top
N11—C17A1.333 (3)N21—C27A1.342 (4)
N11—N121.370 (3)N21—N221.361 (3)
N11—H110.98N21—H210.9799
N12—C131.317 (4)N22—C231.318 (4)
N14—C141.342 (3)N24—C241.348 (3)
N14—C1411.428 (3)N24—C2411.429 (4)
N14—C1471.457 (3)N24—C2471.450 (4)
N15—C141.331 (3)N25—C241.325 (4)
N15—C161.339 (4)N25—C261.342 (3)
N16—C161.340 (4)N26—C261.338 (4)
N16—H16A0.98N26—H26A0.9799
N16—H16B0.9799N26—H26B0.98
N17—C17A1.336 (3)N27—C261.335 (4)
N17—C161.338 (4)N27—C27A1.346 (4)
C13—C13A1.412 (4)C23—C23A1.407 (4)
C13—H130.95C23—H230.95
C13A—C17A1.385 (4)C23A—C27A1.382 (4)
C13A—C141.416 (4)C23A—C241.417 (4)
C141—C1461.360 (4)C241—C2461.369 (4)
C141—C1421.377 (4)C241—C2421.374 (4)
C142—C1431.375 (4)C242—C2431.379 (4)
C142—H1420.95C242—H2420.95
C143—C1441.372 (5)C243—C2441.369 (4)
C143—H1430.95C243—H2430.95
C144—C1451.365 (5)C244—C2451.377 (5)
C144—H1440.95C244—H2440.95
C145—C1461.369 (4)C245—C2461.373 (4)
C145—H1450.95C245—H2450.95
C146—H1460.95C246—H2460.95
C147—C1511.498 (4)C247—C2511.498 (4)
C147—H14A0.99C247—H24A0.99
C147—H14B0.99C247—H24B0.99
C151—C1521.373 (4)C251—C2521.377 (4)
C151—C1561.378 (4)C251—C2561.380 (4)
C152—C1531.382 (4)C252—C2531.393 (4)
C152—H1520.95C252—H2520.95
C153—C1541.365 (5)C253—C2541.364 (5)
C153—H1530.95C253—H2530.95
C154—C1551.371 (5)C254—C2551.369 (5)
C154—H1540.95C254—H2540.95
C155—C1561.377 (5)C255—C2561.365 (5)
C155—H1550.95C255—H2550.95
C156—H1560.95C256—H2560.95
O1—H1A0.9799O2—H2A0.98
O1—H1B0.98O2—H2B0.9799
C17A—N11—N12111.4 (2)C27A—N21—N22111.0 (2)
C17A—N11—H11126.1C27A—N21—H21127.7
N12—N11—H11122.5N22—N21—H21121.3
C13—N12—N11105.7 (2)C23—N22—N21106.0 (2)
C14—N14—C141121.2 (2)C24—N24—C241122.0 (2)
C14—N14—C147121.5 (2)C24—N24—C247120.5 (2)
C141—N14—C147117.2 (2)C241—N24—C247117.5 (2)
C14—N15—C16119.0 (2)C24—N25—C26119.3 (2)
C16—N16—H16A123.7C26—N26—H26A120.8
C16—N16—H16B113.4C26—N26—H26B114.8
H16A—N16—H16B121.3H26A—N26—H26B120.7
C17A—N17—C16112.1 (2)C26—N27—C27A111.3 (2)
N12—C13—C13A110.9 (3)N22—C23—C23A111.0 (3)
N12—C13—H13124.6N22—C23—H23124.5
C13A—C13—H13124.6C23A—C23—H23124.5
C17A—C13A—C13104.6 (2)C27A—C23A—C23104.4 (3)
C17A—C13A—C14114.7 (3)C27A—C23A—C24114.6 (3)
C13—C13A—C14140.5 (3)C23—C23A—C24140.8 (3)
N15—C14—N14117.3 (2)N25—C24—N24117.3 (3)
N15—C14—C13A119.7 (2)N25—C24—C23A119.5 (3)
N14—C14—C13A123.0 (3)N24—C24—C23A123.2 (3)
N17—C16—N15127.2 (3)N27—C26—N26117.3 (2)
N17—C16—N16117.1 (2)N27—C26—N25127.5 (3)
N15—C16—N16115.7 (3)N26—C26—N25115.2 (3)
N11—C17A—N17125.3 (2)N21—C27A—N27124.7 (2)
N11—C17A—C13A107.4 (2)N21—C27A—C23A107.5 (3)
N17—C17A—C13A127.3 (3)N27—C27A—C23A127.8 (3)
C146—C141—C142120.5 (3)C246—C241—C242120.5 (3)
C146—C141—N14120.2 (3)C246—C241—N24119.4 (3)
C142—C141—N14119.4 (3)C242—C241—N24120.1 (3)
C143—C142—C141119.3 (3)C241—C242—C243119.3 (3)
C143—C142—H142120.3C241—C242—H242120.3
C141—C142—H142120.3C243—C242—H242120.3
C144—C143—C142120.0 (3)C244—C243—C242120.5 (3)
C144—C143—H143120.0C244—C243—H243119.8
C142—C143—H143120.0C242—C243—H243119.8
C145—C144—C143119.9 (3)C243—C244—C245119.7 (3)
C145—C144—H144120.0C243—C244—H244120.2
C143—C144—H144120.0C245—C244—H244120.2
C144—C145—C146120.3 (3)C246—C245—C244120.1 (3)
C144—C145—H145119.8C246—C245—H245120.0
C146—C145—H145119.8C244—C245—H245120.0
C141—C146—C145119.9 (3)C241—C246—C245120.0 (3)
C141—C146—H146120.1C241—C246—H246120.0
C145—C146—H146120.1C245—C246—H246120.0
N14—C147—C151115.3 (2)N24—C247—C251115.8 (3)
N14—C147—H14A108.5N24—C247—H24A108.3
C151—C147—H14A108.5C251—C247—H24A108.3
N14—C147—H14B108.5N24—C247—H24B108.3
C151—C147—H14B108.5C251—C247—H24B108.3
H14A—C147—H14B107.5H24A—C247—H24B107.4
C152—C151—C156119.0 (3)C252—C251—C256118.7 (3)
C152—C151—C147123.1 (3)C252—C251—C247123.0 (3)
C156—C151—C147117.9 (3)C256—C251—C247118.3 (3)
C151—C152—C153120.0 (3)C251—C252—C253120.2 (3)
C151—C152—H152120.0C251—C252—H252119.9
C153—C152—H152120.0C253—C252—H252119.9
C154—C153—C152120.8 (3)C254—C253—C252119.9 (3)
C154—C153—H153119.6C254—C253—H253120.0
C152—C153—H153119.6C252—C253—H253120.0
C153—C154—C155119.4 (3)C253—C254—C255119.9 (3)
C153—C154—H154120.3C253—C254—H254120.1
C155—C154—H154120.3C255—C254—H254120.1
C154—C155—C156120.2 (3)C256—C255—C254120.4 (3)
C154—C155—H155119.9C256—C255—H255119.8
C156—C155—H155119.9C254—C255—H255119.8
C155—C156—C151120.6 (3)C255—C256—C251120.8 (3)
C155—C156—H156119.7C255—C256—H256119.6
C151—C156—H156119.7C251—C256—H256119.6
H1A—O1—H1B99.2H2A—O2—H2B101.9
C17A—N11—N12—C130.4 (3)C27A—N21—N22—C230.1 (3)
N11—N12—C13—C13A0.9 (3)N21—N22—C23—C23A0.8 (4)
N12—C13—C13A—C17A1.8 (3)N22—C23—C23A—C27A1.2 (4)
N12—C13—C13A—C14176.3 (3)N22—C23—C23A—C24175.3 (4)
C16—N15—C14—N14178.8 (2)C26—N25—C24—N24176.4 (3)
C16—N15—C14—C13A0.8 (4)C26—N25—C24—C23A2.3 (4)
C141—N14—C14—N15168.3 (2)C241—N24—C24—N25171.8 (3)
C147—N14—C14—N1514.7 (4)C247—N24—C24—N2510.7 (4)
C141—N14—C14—C13A12.1 (4)C241—N24—C24—C23A9.5 (4)
C147—N14—C14—C13A165.0 (3)C247—N24—C24—C23A168.0 (3)
C17A—C13A—C14—N150.0 (4)C27A—C23A—C24—N252.0 (4)
C13—C13A—C14—N15174.1 (3)C23—C23A—C24—N25175.7 (4)
C17A—C13A—C14—N14179.6 (3)C27A—C23A—C24—N24176.7 (3)
C13—C13A—C14—N145.5 (6)C23—C23A—C24—N242.9 (6)
C17A—N17—C16—N153.0 (4)C27A—N27—C26—N26177.1 (3)
C17A—N17—C16—N16176.5 (3)C27A—N27—C26—N251.4 (4)
C14—N15—C16—N172.6 (4)C24—N25—C26—N272.1 (5)
C14—N15—C16—N16176.9 (2)C24—N25—C26—N26176.3 (3)
N12—N11—C17A—N17177.3 (3)N22—N21—C27A—N27177.8 (3)
N12—N11—C17A—C13A1.5 (3)N22—N21—C27A—C23A0.6 (3)
C16—N17—C17A—N11176.6 (3)C26—N27—C27A—N21177.1 (3)
C16—N17—C17A—C13A2.0 (4)C26—N27—C27A—C23A1.0 (4)
C13—C13A—C17A—N112.0 (3)C23—C23A—C27A—N211.1 (3)
C14—C13A—C17A—N11178.1 (2)C24—C23A—C27A—N21177.0 (3)
C13—C13A—C17A—N17176.8 (3)C23—C23A—C27A—N27177.3 (3)
C14—C13A—C17A—N170.7 (4)C24—C23A—C27A—N271.4 (5)
C14—N14—C141—C146108.3 (3)C24—N24—C241—C246113.7 (3)
C147—N14—C141—C14668.9 (3)C247—N24—C241—C24663.9 (4)
C14—N14—C141—C14272.1 (4)C24—N24—C241—C24268.3 (4)
C147—N14—C141—C142110.7 (3)C247—N24—C241—C242114.1 (3)
C146—C141—C142—C1430.3 (4)C246—C241—C242—C2431.3 (4)
N14—C141—C142—C143179.9 (2)N24—C241—C242—C243179.3 (3)
C141—C142—C143—C1440.7 (4)C241—C242—C243—C2441.8 (4)
C142—C143—C144—C1450.3 (5)C242—C243—C244—C2451.3 (5)
C143—C144—C145—C1460.6 (5)C243—C244—C245—C2460.4 (5)
C142—C141—C146—C1450.6 (4)C242—C241—C246—C2450.4 (4)
N14—C141—C146—C145179.0 (3)N24—C241—C246—C245178.4 (3)
C144—C145—C146—C1411.1 (5)C244—C245—C246—C2410.1 (5)
C14—N14—C147—C151100.4 (3)C24—N24—C247—C25193.8 (3)
C141—N14—C147—C15182.4 (3)C241—N24—C247—C25188.6 (3)
N14—C147—C151—C15229.9 (4)N24—C247—C251—C25217.2 (4)
N14—C147—C151—C156151.8 (3)N24—C247—C251—C256163.6 (3)
C156—C151—C152—C1530.2 (5)C256—C251—C252—C2530.5 (4)
C147—C151—C152—C153178.1 (3)C247—C251—C252—C253178.7 (3)
C151—C152—C153—C1540.2 (5)C251—C252—C253—C2540.5 (5)
C152—C153—C154—C1550.1 (5)C252—C253—C254—C2550.3 (5)
C153—C154—C155—C1560.2 (6)C253—C254—C255—C2560.0 (5)
C154—C155—C156—C1510.2 (5)C254—C255—C256—C2510.0 (5)
C152—C151—C156—C1550.0 (5)C252—C251—C256—C2550.2 (4)
C147—C151—C156—C155178.3 (3)C247—C251—C256—C255179.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N120.981.892.813 (3)155
O2—H2A···N220.981.832.774 (3)160
O1—H1B···N15i0.982.463.114 (3)124
O2—H2B···N25ii0.982.543.160 (3)121
N11—H11···N270.981.902.872 (3)172
N16—H16A···O20.982.123.045 (3)156
N16—H16B···O1ii0.982.112.988 (3)148
N21—H21···N170.981.852.828 (3)172
N26—H26A···O10.982.002.941 (3)161
N26—H26B···O2i0.982.082.997 (3)156
C13—H13···Cg20.952.743.472 (3)134
C23—H23···Cg30.952.783.526 (3)136
C244—H244···Cg4iii0.952.653.563 (3)161
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x1/2, y+1/2, z1/2.
(IX) (4-(Pyrrolidin-1-yl)-1/H/-pyrazolo[3,4-/d/]pyrimidin-6-amine) ethanol hemisolvate hemihydrate top
Crystal data top
2(C9H12N6)·C2H6O·H2OZ = 2
Mr = 472.58F(000) = 504
Triclinic, P1Dx = 1.367 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9342 (15) ÅCell parameters from 5275 reflections
b = 8.9219 (19) Åθ = 3.0–27.5°
c = 16.767 (3) ŵ = 0.10 mm1
α = 76.855 (16)°T = 120 K
β = 83.505 (14)°Plate, colourless
γ = 88.003 (17)°0.46 × 0.19 × 0.10 mm
V = 1148.3 (4) Å3
Data collection top
Bruker-Nonius KappaCCD
diffractometer
5275 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode3372 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
ϕ & ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
h = 1010
Tmin = 0.967, Tmax = 0.991k = 1111
28718 measured reflectionsl = 2121
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0811P)2 + 0.4703P]
where P = (Fo2 + 2Fc2)/3
5275 reflections(Δ/σ)max < 0.001
308 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
2(C9H12N6)·C2H6O·H2Oγ = 88.003 (17)°
Mr = 472.58V = 1148.3 (4) Å3
Triclinic, P1Z = 2
a = 7.9342 (15) ÅMo Kα radiation
b = 8.9219 (19) ŵ = 0.10 mm1
c = 16.767 (3) ÅT = 120 K
α = 76.855 (16)°0.46 × 0.19 × 0.10 mm
β = 83.505 (14)°
Data collection top
Bruker-Nonius KappaCCD
diffractometer
5275 independent reflections
Absorption correction: multi-scan
SADABS 2.10 (Sheldrick, 2003)
3372 reflections with I > 2σ(I)
Tmin = 0.967, Tmax = 0.991Rint = 0.064
28718 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.163H-atom parameters constrained
S = 1.05Δρmax = 0.32 e Å3
5275 reflectionsΔρmin = 0.32 e Å3
308 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.4818 (2)0.17503 (19)0.42237 (10)0.0200 (4)
N120.4935 (2)0.29356 (19)0.35371 (10)0.0224 (4)
N140.2001 (2)0.58580 (18)0.50653 (10)0.0196 (4)
N150.2139 (2)0.35172 (18)0.59792 (10)0.0192 (4)
N160.2277 (2)0.12251 (19)0.69327 (10)0.0236 (4)
N170.3589 (2)0.12835 (18)0.56290 (10)0.0188 (4)
C130.4138 (3)0.4119 (2)0.37627 (13)0.0220 (5)
C13A0.3469 (3)0.3727 (2)0.46033 (12)0.0174 (4)
C140.2530 (3)0.4392 (2)0.52157 (12)0.0180 (4)
C160.2671 (3)0.2031 (2)0.61433 (12)0.0185 (4)
C17A0.3944 (3)0.2189 (2)0.48712 (12)0.0187 (4)
C1410.1108 (3)0.6551 (2)0.57069 (12)0.0202 (4)
C1420.0618 (3)0.8156 (2)0.52534 (13)0.0232 (5)
C1430.1870 (3)0.8511 (2)0.44775 (13)0.0239 (5)
C1440.2326 (3)0.6952 (2)0.42737 (13)0.0220 (5)
N210.8747 (2)0.3347 (2)0.04059 (10)0.0234 (4)
N220.7905 (2)0.2106 (2)0.09043 (11)0.0271 (4)
N240.8217 (2)0.00084 (19)0.12914 (11)0.0232 (4)
N250.9639 (2)0.22692 (19)0.17981 (10)0.0208 (4)
N261.0936 (2)0.4576 (2)0.23629 (11)0.0271 (4)
N270.9968 (2)0.41587 (19)0.09901 (10)0.0220 (4)
C230.7762 (3)0.1126 (2)0.04324 (13)0.0252 (5)
C23A0.8510 (3)0.1703 (2)0.03810 (12)0.0195 (4)
C240.8786 (3)0.1298 (2)0.11606 (13)0.0205 (4)
C261.0158 (3)0.3643 (2)0.16940 (13)0.0208 (4)
C27A0.9138 (3)0.3148 (2)0.03629 (12)0.0206 (4)
C2410.8251 (3)0.0333 (3)0.21138 (14)0.0292 (5)
C2420.6848 (3)0.1513 (3)0.19921 (15)0.0347 (6)
C2430.6924 (3)0.2407 (3)0.11097 (15)0.0316 (5)
C2440.7275 (3)0.1167 (2)0.06583 (14)0.0257 (5)
O310.5139 (2)0.25081 (19)0.76120 (10)0.0402 (4)
C310.4618 (3)0.2639 (3)0.84302 (14)0.0329 (6)
C320.5172 (4)0.4156 (3)0.85512 (17)0.0421 (6)
O10.77435 (19)0.22078 (16)0.25481 (9)0.0255 (4)
H110.53050.08760.42170.024*
H16A0.14780.15880.72280.028*
H16B0.23890.02400.70270.028*
H130.40260.51040.34090.026*
H41A0.18580.66040.61330.024*
H41B0.00890.59510.59730.024*
H42A0.07150.89130.55950.028*
H42B0.05620.81750.51110.028*
H43A0.28940.90140.45780.029*
H43B0.13440.91990.40200.029*
H44A0.16050.67360.38690.026*
H44B0.35320.69150.40490.026*
H210.90170.40910.06140.028*
H26A1.11420.42890.28210.033*
H26B1.12300.54850.23430.033*
H230.72230.01550.06170.030*
H41C0.93640.07640.22860.035*
H41D0.80070.06070.25290.035*
H42C0.57290.10030.20630.042*
H42D0.70690.21950.23840.042*
H43C0.78460.31880.10750.038*
H43D0.58350.29250.08800.038*
H44C0.62040.07310.04390.031*
H44D0.79590.15860.01980.031*
H310.43340.20730.74980.060*
H31A0.51230.17890.88220.040*
H31B0.33680.25610.85400.040*
H32A0.64010.42570.84080.063*
H32B0.48840.42070.91280.063*
H32C0.45930.49940.81960.063*
H1A0.68100.24070.27660.038*
H1B0.76590.22330.20620.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0261 (10)0.0159 (8)0.0173 (9)0.0022 (7)0.0019 (7)0.0047 (7)
N120.0293 (10)0.0191 (9)0.0175 (9)0.0006 (7)0.0013 (7)0.0033 (7)
N140.0258 (9)0.0149 (8)0.0174 (9)0.0008 (7)0.0007 (7)0.0040 (7)
N150.0239 (9)0.0147 (8)0.0184 (9)0.0001 (7)0.0001 (7)0.0037 (7)
N160.0342 (11)0.0163 (9)0.0177 (9)0.0019 (8)0.0054 (8)0.0026 (7)
N170.0224 (9)0.0154 (8)0.0174 (9)0.0010 (7)0.0014 (7)0.0032 (7)
C130.0265 (11)0.0192 (10)0.0192 (11)0.0005 (8)0.0011 (9)0.0030 (8)
C13A0.0211 (10)0.0145 (9)0.0165 (10)0.0018 (8)0.0012 (8)0.0037 (8)
C140.0200 (10)0.0151 (10)0.0192 (10)0.0021 (8)0.0018 (8)0.0044 (8)
C160.0216 (11)0.0162 (10)0.0184 (10)0.0025 (8)0.0020 (8)0.0051 (8)
C17A0.0195 (10)0.0183 (10)0.0192 (10)0.0012 (8)0.0000 (8)0.0067 (8)
C1410.0242 (11)0.0182 (10)0.0191 (11)0.0001 (8)0.0006 (9)0.0074 (8)
C1420.0285 (12)0.0171 (10)0.0246 (11)0.0016 (9)0.0031 (9)0.0060 (9)
C1430.0305 (12)0.0160 (10)0.0244 (11)0.0009 (9)0.0001 (9)0.0044 (9)
C1440.0276 (11)0.0185 (10)0.0191 (11)0.0002 (8)0.0003 (9)0.0034 (8)
N210.0327 (11)0.0209 (9)0.0180 (9)0.0079 (8)0.0017 (8)0.0081 (7)
N220.0348 (11)0.0244 (10)0.0213 (10)0.0073 (8)0.0021 (8)0.0049 (8)
N240.0291 (10)0.0201 (9)0.0222 (9)0.0044 (7)0.0015 (8)0.0088 (7)
N250.0254 (10)0.0192 (9)0.0188 (9)0.0030 (7)0.0004 (7)0.0072 (7)
N260.0412 (12)0.0208 (9)0.0202 (10)0.0073 (8)0.0036 (8)0.0090 (8)
N270.0285 (10)0.0212 (9)0.0177 (9)0.0026 (8)0.0007 (8)0.0085 (7)
C230.0321 (12)0.0212 (11)0.0223 (11)0.0064 (9)0.0006 (9)0.0051 (9)
C23A0.0225 (11)0.0169 (10)0.0194 (10)0.0017 (8)0.0008 (8)0.0051 (8)
C240.0205 (11)0.0192 (10)0.0218 (11)0.0003 (8)0.0008 (9)0.0052 (9)
C260.0233 (11)0.0208 (10)0.0184 (10)0.0010 (8)0.0011 (8)0.0051 (8)
C27A0.0226 (11)0.0206 (10)0.0194 (11)0.0007 (8)0.0012 (8)0.0064 (8)
C2410.0356 (13)0.0314 (12)0.0238 (12)0.0052 (10)0.0014 (10)0.0147 (10)
C2420.0386 (14)0.0350 (13)0.0365 (14)0.0097 (11)0.0038 (11)0.0192 (11)
C2430.0353 (13)0.0215 (11)0.0407 (14)0.0056 (10)0.0035 (11)0.0120 (10)
C2440.0287 (12)0.0217 (11)0.0273 (12)0.0051 (9)0.0023 (10)0.0065 (9)
O310.0419 (11)0.0421 (10)0.0373 (10)0.0078 (8)0.0027 (8)0.0101 (8)
C310.0355 (14)0.0317 (13)0.0302 (13)0.0015 (10)0.0057 (11)0.0031 (10)
C320.0528 (17)0.0349 (14)0.0414 (15)0.0034 (12)0.0102 (13)0.0111 (12)
O10.0329 (9)0.0242 (8)0.0190 (8)0.0008 (7)0.0021 (6)0.0067 (6)
Geometric parameters (Å, º) top
N11—C17A1.348 (2)N24—C2441.459 (3)
N11—N121.371 (2)N24—C2411.469 (3)
N11—H110.86N25—C241.344 (3)
N12—C131.318 (3)N25—C261.360 (3)
N14—C141.337 (3)N26—C261.337 (3)
N14—C1441.460 (3)N26—H26A0.86
N14—C1411.463 (2)N26—H26B0.86
N15—C141.348 (3)N27—C27A1.344 (3)
N15—C161.354 (2)N27—C261.353 (3)
N16—C161.362 (3)C23—C23A1.413 (3)
N16—H16A0.86C23—H230.95
N16—H16B0.86C23A—C27A1.406 (3)
N17—C161.343 (2)C23A—C241.425 (3)
N17—C17A1.347 (3)C241—C2421.524 (3)
C13—C13A1.418 (3)C241—H41C0.99
C13—H130.95C241—H41D0.99
C13A—C17A1.396 (3)C242—C2431.519 (3)
C13A—C141.426 (3)C242—H42C0.99
C141—C1421.521 (3)C242—H42D0.99
C141—H41A0.99C243—C2441.524 (3)
C141—H41B0.99C243—H43C0.99
C142—C1431.524 (3)C243—H43D0.99
C142—H42A0.99C244—H44C0.99
C142—H42B0.99C244—H44D0.99
C143—C1441.528 (3)O31—C311.417 (3)
C143—H43A0.99O31—H310.82
C143—H43B0.99C31—C321.500 (3)
C144—H44A0.99C31—H31A0.99
C144—H44B0.99C31—H31B0.99
N21—C27A1.341 (3)C32—H32A0.98
N21—N221.370 (2)C32—H32B0.98
N21—H210.86C32—H32C0.98
N22—C231.321 (3)O1—H1A0.82
N24—C241.337 (3)O1—H1B0.82
C17A—N11—N12111.05 (16)C24—N25—C26119.30 (17)
C17A—N11—H11127.6C26—N26—H26A121.0
N12—N11—H11121.3C26—N26—H26B120.3
C13—N12—N11106.16 (16)H26A—N26—H26B118.7
C14—N14—C144124.51 (17)C27A—N27—C26112.01 (17)
C14—N14—C141122.37 (17)N22—C23—C23A111.52 (19)
C144—N14—C141113.03 (15)N22—C23—H23124.2
C14—N15—C16118.66 (17)C23A—C23—H23124.2
C16—N16—H16A117.3C27A—C23A—C23104.06 (18)
C16—N16—H16B117.4C27A—C23A—C24115.12 (18)
H16A—N16—H16B117.0C23—C23A—C24140.82 (19)
C16—N17—C17A112.01 (16)N24—C24—N25118.02 (18)
N12—C13—C13A111.11 (18)N24—C24—C23A122.78 (18)
N12—C13—H13124.4N25—C24—C23A119.20 (18)
C13A—C13—H13124.4N26—C26—N27116.94 (18)
C17A—C13A—C13104.35 (17)N26—C26—N25116.04 (18)
C17A—C13A—C14115.08 (18)N27—C26—N25127.02 (18)
C13—C13A—C14140.57 (18)N21—C27A—N27125.65 (18)
N14—C14—N15117.88 (17)N21—C27A—C23A107.05 (18)
N14—C14—C13A122.73 (18)N27—C27A—C23A127.29 (18)
N15—C14—C13A119.39 (17)N24—C241—C242102.75 (17)
N17—C16—N15127.64 (18)N24—C241—H41C111.2
N17—C16—N16116.66 (17)C242—C241—H41C111.2
N15—C16—N16115.65 (17)N24—C241—H41D111.2
N17—C17A—N11125.47 (18)C242—C241—H41D111.2
N17—C17A—C13A127.19 (18)H41C—C241—H41D109.1
N11—C17A—C13A107.33 (17)C243—C242—C241103.15 (19)
N14—C141—C142104.46 (16)C243—C242—H42C111.1
N14—C141—H41A110.9C241—C242—H42C111.1
C142—C141—H41A110.9C243—C242—H42D111.1
N14—C141—H41B110.9C241—C242—H42D111.1
C142—C141—H41B110.9H42C—C242—H42D109.1
H41A—C141—H41B108.9C242—C243—C244103.39 (18)
C141—C142—C143104.88 (16)C242—C243—H43C111.1
C141—C142—H42A110.8C244—C243—H43C111.1
C143—C142—H42A110.8C242—C243—H43D111.1
C141—C142—H42B110.8C244—C243—H43D111.1
C143—C142—H42B110.8H43C—C243—H43D109.0
H42A—C142—H42B108.8N24—C244—C243103.74 (17)
C142—C143—C144105.28 (16)N24—C244—H44C111.0
C142—C143—H43A110.7C243—C244—H44C111.0
C144—C143—H43A110.7N24—C244—H44D111.0
C142—C143—H43B110.7C243—C244—H44D111.0
C144—C143—H43B110.7H44C—C244—H44D109.0
H43A—C143—H43B108.8C31—O31—H31102.8
N14—C144—C143103.77 (16)O31—C31—C32109.9 (2)
N14—C144—H44A111.0O31—C31—H31A109.7
C143—C144—H44A111.0C32—C31—H31A109.7
N14—C144—H44B111.0O31—C31—H31B109.7
C143—C144—H44B111.0C32—C31—H31B109.7
H44A—C144—H44B109.0H31A—C31—H31B108.2
C27A—N21—N22111.67 (17)C31—C32—H32A109.5
C27A—N21—H21128.8C31—C32—H32B109.5
N22—N21—H21119.4H32A—C32—H32B109.5
C23—N22—N21105.70 (17)C31—C32—H32C109.5
C24—N24—C244124.01 (17)H32A—C32—H32C109.5
C24—N24—C241123.39 (17)H32B—C32—H32C109.5
C244—N24—C241112.03 (16)H1A—O1—H1B108.2
C17A—N11—N12—C130.4 (2)C27A—N21—N22—C230.5 (2)
N11—N12—C13—C13A0.5 (2)N21—N22—C23—C23A0.2 (2)
N12—C13—C13A—C17A0.3 (2)N22—C23—C23A—C27A0.1 (2)
N12—C13—C13A—C14179.9 (2)N22—C23—C23A—C24179.1 (3)
C144—N14—C14—N15179.75 (18)C244—N24—C24—N25179.96 (18)
C141—N14—C14—N153.5 (3)C241—N24—C24—N259.3 (3)
C144—N14—C14—C13A0.7 (3)C244—N24—C24—C23A0.7 (3)
C141—N14—C14—C13A177.02 (19)C241—N24—C24—C23A170.0 (2)
C16—N15—C14—N14179.71 (18)C26—N25—C24—N24176.66 (19)
C16—N15—C14—C13A0.8 (3)C26—N25—C24—C23A2.7 (3)
C17A—C13A—C14—N14178.94 (19)C27A—C23A—C24—N24177.53 (19)
C13—C13A—C14—N140.6 (4)C23—C23A—C24—N241.6 (4)
C17A—C13A—C14—N151.6 (3)C27A—C23A—C24—N251.8 (3)
C13—C13A—C14—N15178.9 (2)C23—C23A—C24—N25179.1 (2)
C17A—N17—C16—N151.2 (3)C27A—N27—C26—N26178.56 (18)
C17A—N17—C16—N16178.57 (18)C27A—N27—C26—N251.4 (3)
C14—N15—C16—N170.7 (3)C24—N25—C26—N26177.31 (18)
C14—N15—C16—N16178.14 (18)C24—N25—C26—N272.6 (3)
C16—N17—C17A—N11178.84 (19)N22—N21—C27A—N27179.72 (19)
C16—N17—C17A—C13A0.2 (3)N22—N21—C27A—C23A0.5 (2)
N12—N11—C17A—N17178.95 (19)C26—N27—C27A—N21179.3 (2)
N12—N11—C17A—C13A0.2 (2)C26—N27—C27A—C23A0.4 (3)
C13—C13A—C17A—N17179.2 (2)C23—C23A—C27A—N210.4 (2)
C14—C13A—C17A—N171.1 (3)C24—C23A—C27A—N21179.04 (18)
C13—C13A—C17A—N110.0 (2)C23—C23A—C27A—N27179.9 (2)
C14—C13A—C17A—N11179.72 (17)C24—C23A—C27A—N270.7 (3)
C14—N14—C141—C142175.13 (19)C24—N24—C241—C242156.0 (2)
C144—N14—C141—C1428.2 (2)C244—N24—C241—C24215.7 (2)
N14—C141—C142—C14323.3 (2)N24—C241—C242—C24333.2 (2)
C141—C142—C143—C14429.8 (2)C241—C242—C243—C24438.8 (2)
C14—N14—C144—C143166.35 (19)C24—N24—C244—C243180.0 (2)
C141—N14—C144—C14310.2 (2)C241—N24—C244—C2438.3 (2)
C142—C143—C144—N1424.5 (2)C242—C243—C244—N2429.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N120.821.972.773 (2)164
O1—H1B···N220.821.962.767 (2)169
N11—H11···N17i0.862.062.918 (2)172
N21—H21···N27ii0.862.032.886 (2)170
N16—H16A···N25iii0.862.243.088 (2)169
N26—H26A···N15iv0.862.323.172 (3)171
N16—H16B···O1i0.862.142.988 (2)168
N26—H26B···O1ii0.862.183.026 (2)168
O31—H31···N160.822.213.021 (2)168
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y+1, z; (iii) x1, y, z+1; (iv) x+1, y, z1.

Experimental details

(I)(II)(III)(IV)
Crystal data
Chemical formulaC12H12N6C12H18N6C11H9ClN6C11H17N7O
Mr240.28246.33260.69263.32
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/nMonoclinic, P21/cOrthorhombic, Pbca
Temperature (K)120120120120
a, b, c (Å)10.6661 (12), 7.7279 (9), 14.359 (2)11.2407 (10), 7.3654 (5), 15.8178 (12)11.1960 (8), 8.5040 (8), 13.3815 (12)7.0297 (9), 13.859 (3), 25.766 (6)
α, β, γ (°)90, 100.071 (7), 9090, 106.005 (7), 9090, 120.674 (5), 9090, 90, 90
V3)1165.3 (3)1258.83 (17)1095.80 (16)2510.2 (9)
Z4448
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.090.090.340.10
Crystal size (mm)0.58 × 0.41 × 0.340.32 × 0.28 × 0.180.55 × 0.21 × 0.100.20 × 0.10 × 0.08
Data collection
DiffractometerBruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Tmin, Tmax0.953, 0.9700.964, 0.9850.836, 0.9670.985, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
27117, 2674, 1737 32264, 2885, 1763 26526, 2515, 1452 59170, 2877, 1479
Rint0.0540.1100.1080.171
(sin θ/λ)max1)0.6500.6500.6500.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.169, 1.10 0.061, 0.142, 1.06 0.060, 0.183, 1.06 0.071, 0.224, 1.01
No. of reflections2674288525152877
No. of parameters164164163172
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.430.29, 0.340.42, 0.470.33, 0.36


(V)(VI)(VII)(VIII)
Crystal data
Chemical formulaC13H14N6·H2O2(C13H14N6)·H2O2(C13H14N6O)·H2OC18H16N6·H2O
Mr272.32526.62558.62334.38
Crystal system, space groupOrthorhombic, PbcaMonoclinic, C2/cTriclinic, P1Monoclinic, P21/n
Temperature (K)120120120120
a, b, c (Å)16.5577 (12), 8.6833 (3), 18.4640 (13)17.642 (3), 18.278 (3), 8.3034 (18)8.9516 (5), 12.0627 (7), 12.9053 (7)10.1880 (11), 9.5136 (10), 33.695 (4)
α, β, γ (°)90, 90, 9090, 103.512 (17), 9091.612 (4), 92.065 (3), 95.259 (5)90, 93.131 (7), 90
V3)2654.7 (3)2603.4 (9)1386.06 (13)3261.0 (6)
Z8428
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.090.090.090.09
Crystal size (mm)0.37 × 0.24 × 0.230.45 × 0.21 × 0.070.54 × 0.48 × 0.400.44 × 0.33 × 0.24
Data collection
DiffractometerBruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Bruker-Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Multi-scan
SADABS 2.10 (Sheldrick, 2003)
Tmin, Tmax0.969, 0.9790.966, 0.9940.955, 0.9630.968, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
61337, 3046, 2146 32439, 2987, 1829 31433, 6316, 4620 83278, 7493, 3887
Rint0.0660.0600.0300.095
(sin θ/λ)max1)0.6500.6500.6500.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.122, 1.09 0.052, 0.159, 1.07 0.046, 0.104, 1.11 0.068, 0.220, 1.04
No. of reflections3046298763167493
No. of parameters183178374451
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.290.27, 0.260.26, 0.280.42, 0.33


(IX)
Crystal data
Chemical formula2(C9H12N6)·C2H6O·H2O
Mr472.58
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)7.9342 (15), 8.9219 (19), 16.767 (3)
α, β, γ (°)76.855 (16), 83.505 (14), 88.003 (17)
V3)1148.3 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.46 × 0.19 × 0.10
Data collection
DiffractometerBruker-Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
SADABS 2.10 (Sheldrick, 2003)
Tmin, Tmax0.967, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
28718, 5275, 3372
Rint0.064
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.163, 1.05
No. of reflections5275
No. of parameters308
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.32

Computer programs: COLLECT (Hooft, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), Sir2004 (Burla et al., 2005), OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

 

Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds