Anhydrous versus hydrated N⁴-substituted 1H-pyrazolo[3,4-d]pyrimidine-4,6-diamines: hydrogen bonding in two and three dimensions

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 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.

S1. Comment

In full text version

S2. Experimental

In full text version

S3. Refinement

In full text version

Computing details

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

In full text version

(I) N⁴-Methyl-N⁴-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

Crystal data

C12H12N6	F(000) = 504
Mr = 240.28	Dx = 1.369 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2674 reflections
a = 10.6661 (12) Å	θ = 3.0–27.5°
b = 7.7279 (9) Å	µ = 0.09 mm^−1
c = 14.359 (2) Å	T = 120 K
β = 100.071 (7)°	Block, colourless
V = 1165.3 (3) Å^3	0.58 × 0.41 × 0.34 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2674 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1737 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
ϕ & ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −13→13
Tmin = 0.953, Tmax = 0.970	k = −10→10
27117 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0702P)^2 + 1.151P] where P = (Fo^2 + 2Fc^2)/3
2674 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.61207 (17)	0.1677 (2)	0.51997 (12)	0.0236 (4)
N4	0.58721 (17)	0.5923 (2)	0.28872 (13)	0.0246 (4)
N7	0.43838 (17)	0.1459 (2)	0.39011 (12)	0.0231 (4)
N5	0.43211 (17)	0.3819 (2)	0.27905 (12)	0.0219 (4)
N6	0.28309 (17)	0.1679 (3)	0.25756 (13)	0.0284 (5)
C3A	0.6022 (2)	0.3725 (3)	0.41199 (15)	0.0219 (5)
C41	0.7043 (2)	0.6662 (3)	0.33631 (15)	0.0224 (5)
C4	0.5403 (2)	0.4506 (3)	0.32582 (14)	0.0207 (5)
N2	0.71484 (18)	0.2724 (3)	0.54971 (13)	0.0279 (5)
C7A	0.54342 (19)	0.2237 (3)	0.43802 (14)	0.0203 (5)
C45	0.9324 (2)	0.6619 (3)	0.36752 (17)	0.0298 (5)
C44	0.9319 (2)	0.7872 (3)	0.43652 (18)	0.0315 (6)
C6	0.3885 (2)	0.2322 (3)	0.31138 (15)	0.0220 (5)
C3	0.7090 (2)	0.3953 (3)	0.48542 (16)	0.0276 (5)
C47	0.5260 (2)	0.6711 (3)	0.20045 (16)	0.0308 (6)
C42	0.7037 (2)	0.7944 (3)	0.40308 (16)	0.0271 (5)
C46	0.8186 (2)	0.6025 (3)	0.31655 (16)	0.0274 (5)
C43	0.8179 (2)	0.8547 (3)	0.45335 (18)	0.0328 (6)
H1	0.6035	0.0744	0.5510	0.028*
H6A	0.2629	0.2007	0.1996	0.034*
H6B	0.2505	0.0699	0.2687	0.034*
H45	1.0108	0.6170	0.3553	0.036*
H44	1.0101	0.8267	0.4723	0.038*
H3	0.7685	0.4873	0.4879	0.033*
H47A	0.4661	0.5886	0.1650	0.046*
H47B	0.5908	0.7025	0.1627	0.046*
H47C	0.4800	0.7752	0.2141	0.046*
H42	0.6254	0.8410	0.4145	0.033*
H46	0.8185	0.5185	0.2682	0.033*
H43	0.8180	0.9427	0.4996	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0237 (9)	0.0245 (10)	0.0203 (9)	−0.0047 (7)	−0.0025 (7)	0.0038 (7)
N4	0.0273 (10)	0.0225 (10)	0.0215 (9)	−0.0056 (8)	−0.0029 (7)	0.0041 (7)
N7	0.0228 (9)	0.0244 (10)	0.0204 (9)	−0.0027 (7)	−0.0009 (7)	0.0023 (7)
N5	0.0219 (9)	0.0218 (9)	0.0209 (9)	−0.0017 (7)	0.0005 (7)	0.0015 (7)
N6	0.0276 (10)	0.0300 (11)	0.0243 (10)	−0.0099 (8)	−0.0048 (8)	0.0048 (8)
C3A	0.0208 (11)	0.0241 (11)	0.0194 (10)	−0.0017 (9)	−0.0001 (8)	0.0001 (9)
C41	0.0245 (11)	0.0202 (11)	0.0215 (10)	−0.0034 (9)	0.0008 (8)	0.0030 (9)
C4	0.0215 (10)	0.0195 (10)	0.0207 (10)	−0.0003 (8)	0.0024 (8)	−0.0011 (8)
N2	0.0268 (10)	0.0285 (10)	0.0253 (10)	−0.0069 (8)	−0.0041 (8)	0.0015 (8)
C7A	0.0194 (10)	0.0213 (11)	0.0196 (10)	−0.0010 (8)	0.0014 (8)	0.0001 (8)
C45	0.0247 (12)	0.0327 (13)	0.0336 (13)	0.0010 (10)	0.0091 (10)	0.0039 (10)
C44	0.0255 (12)	0.0324 (13)	0.0346 (13)	−0.0077 (10)	−0.0001 (10)	0.0000 (11)
C6	0.0213 (10)	0.0232 (11)	0.0203 (10)	0.0003 (8)	0.0005 (8)	0.0008 (9)
C3	0.0264 (12)	0.0289 (12)	0.0249 (11)	−0.0065 (9)	−0.0030 (9)	0.0028 (9)
C47	0.0329 (13)	0.0302 (13)	0.0266 (12)	−0.0056 (10)	−0.0025 (10)	0.0076 (10)
C42	0.0262 (11)	0.0271 (12)	0.0277 (12)	−0.0005 (9)	0.0039 (9)	−0.0020 (10)
C46	0.0295 (12)	0.0269 (12)	0.0253 (11)	−0.0007 (10)	0.0038 (9)	−0.0002 (9)
C43	0.0325 (13)	0.0311 (13)	0.0336 (13)	−0.0044 (10)	0.0020 (10)	−0.0071 (10)

Geometric parameters (Å, º)

N1—C7A	1.344 (3)	C41—C42	1.380 (3)
N1—N2	1.369 (3)	C41—C46	1.389 (3)
N1—H1	0.86	N2—C3	1.318 (3)
N4—C4	1.352 (3)	C45—C46	1.382 (3)
N4—C41	1.433 (3)	C45—C44	1.386 (3)
N4—C47	1.454 (3)	C45—H45	0.95
N7—C6	1.340 (3)	C44—C43	1.383 (3)
N7—C7A	1.349 (3)	C44—H44	0.95
N5—C4	1.339 (3)	C3—H3	0.95
N5—C6	1.358 (3)	C47—H47A	0.98
N6—C6	1.343 (3)	C47—H47B	0.98
N6—H6A	0.86	C47—H47C	0.98
N6—H6B	0.86	C42—C43	1.384 (3)
C3A—C7A	1.392 (3)	C42—H42	0.95
C3A—C3	1.422 (3)	C46—H46	0.95
C3A—C4	1.430 (3)	C43—H43	0.95
C7A—N1—N2	111.51 (18)	C44—C45—H45	120.1
C7A—N1—H1	129.2	C43—C44—C45	120.1 (2)
N2—N1—H1	119.0	C43—C44—H44	119.9
C4—N4—C41	119.13 (17)	C45—C44—H44	119.9
C4—N4—C47	122.81 (18)	N7—C6—N6	118.1 (2)
C41—N4—C47	118.03 (18)	N7—C6—N5	127.06 (19)
C6—N7—C7A	112.36 (18)	N6—C6—N5	114.87 (19)
C4—N5—C6	118.87 (18)	N2—C3—C3A	111.3 (2)
C6—N6—H6A	119.4	N2—C3—H3	124.3
C6—N6—H6B	122.9	C3A—C3—H3	124.3
H6A—N6—H6B	113.5	N4—C47—H47A	109.5
C7A—C3A—C3	104.07 (19)	N4—C47—H47B	109.5
C7A—C3A—C4	114.79 (19)	H47A—C47—H47B	109.5
C3—C3A—C4	141.1 (2)	N4—C47—H47C	109.5
C42—C41—C46	120.5 (2)	H47A—C47—H47C	109.5
C42—C41—N4	120.5 (2)	H47B—C47—H47C	109.5
C46—C41—N4	118.9 (2)	C41—C42—C43	119.6 (2)
N5—C4—N4	118.01 (19)	C41—C42—H42	120.2
N5—C4—C3A	119.60 (19)	C43—C42—H42	120.2
N4—C4—C3A	122.39 (19)	C45—C46—C41	119.7 (2)
C3—N2—N1	105.67 (17)	C45—C46—H46	120.2
N1—C7A—N7	125.4 (2)	C41—C46—H46	120.2
N1—C7A—C3A	107.42 (18)	C44—C43—C42	120.2 (2)
N7—C7A—C3A	127.15 (19)	C44—C43—H43	119.9
C46—C45—C44	119.9 (2)	C42—C43—H43	119.9
C46—C45—H45	120.1
C4—N4—C41—C42	−91.1 (3)	C3—C3A—C7A—N1	0.1 (2)
C47—N4—C41—C42	90.8 (3)	C4—C3A—C7A—N1	−179.53 (18)
C4—N4—C41—C46	86.7 (3)	C3—C3A—C7A—N7	−178.7 (2)
C47—N4—C41—C46	−91.4 (3)	C4—C3A—C7A—N7	1.6 (3)
C6—N5—C4—N4	175.18 (19)	C46—C45—C44—C43	−1.0 (4)
C6—N5—C4—C3A	−4.5 (3)	C7A—N7—C6—N6	−179.79 (19)
C41—N4—C4—N5	−178.66 (19)	C7A—N7—C6—N5	−0.5 (3)
C47—N4—C4—N5	−0.6 (3)	C4—N5—C6—N7	3.9 (3)
C41—N4—C4—C3A	1.0 (3)	C4—N5—C6—N6	−176.8 (2)
C47—N4—C4—C3A	179.0 (2)	N1—N2—C3—C3A	−0.3 (3)
C7A—C3A—C4—N5	2.0 (3)	C7A—C3A—C3—N2	0.1 (3)
C3—C3A—C4—N5	−177.5 (3)	C4—C3A—C3—N2	179.6 (3)
C7A—C3A—C4—N4	−177.7 (2)	C46—C41—C42—C43	−2.7 (3)
C3—C3A—C4—N4	2.9 (4)	N4—C41—C42—C43	175.1 (2)
C7A—N1—N2—C3	0.4 (3)	C44—C45—C46—C41	−1.4 (3)
N2—N1—C7A—N7	178.6 (2)	C42—C41—C46—C45	3.2 (3)
N2—N1—C7A—C3A	−0.3 (2)	N4—C41—C46—C45	−174.5 (2)
C6—N7—C7A—N1	179.0 (2)	C45—C44—C43—C42	1.6 (4)
C6—N7—C7A—C3A	−2.3 (3)	C41—C42—C43—C44	0.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N7^i	0.86	1.99	2.841 (3)	172
N6—H6A···N2^ii	0.86	2.13	2.982 (3)	168
N6—H6B···N5^iii	0.86	2.43	3.164 (3)	144
C3—H3···Cg1	0.95	2.48	3.255 (3)	138

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2.

(II) N⁴-(Cyclohexyl)-N⁴-methyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

Crystal data

C12H18N6	F(000) = 528
Mr = 246.33	Dx = 1.300 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2885 reflections
a = 11.2407 (10) Å	θ = 3.1–27.5°
b = 7.3654 (5) Å	µ = 0.09 mm^−1
c = 15.8178 (12) Å	T = 120 K
β = 106.005 (7)°	Block, colourless
V = 1258.83 (17) Å^3	0.32 × 0.28 × 0.18 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2885 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1763 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.110
ϕ & ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −14→14
Tmin = 0.964, Tmax = 0.985	k = −9→9
32264 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0435P)^2 + 1.3394P] where P = (Fo^2 + 2Fc^2)/3
2885 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.50121 (18)	0.1950 (3)	0.56711 (12)	0.0193 (5)
N2	0.51249 (18)	0.3163 (3)	0.63479 (12)	0.0212 (5)
N5	0.21659 (18)	0.3765 (3)	0.37242 (12)	0.0187 (4)
N7	0.37379 (18)	0.1458 (3)	0.42100 (12)	0.0170 (4)
N4	0.18037 (19)	0.6089 (3)	0.45963 (13)	0.0210 (5)
N6	0.2389 (2)	0.1435 (3)	0.28273 (13)	0.0259 (5)
C3	0.4245 (2)	0.4373 (3)	0.60584 (15)	0.0209 (5)
C3A	0.3511 (2)	0.3957 (3)	0.51885 (14)	0.0172 (5)
C4	0.2487 (2)	0.4622 (3)	0.45064 (15)	0.0179 (5)
C6	0.2785 (2)	0.2243 (3)	0.36188 (14)	0.0173 (5)
C7A	0.4064 (2)	0.2389 (3)	0.49745 (14)	0.0158 (5)
C41	0.1923 (2)	0.6918 (3)	0.54590 (16)	0.0216 (5)
C42	0.0670 (2)	0.7503 (4)	0.55806 (16)	0.0254 (6)
C43	0.0843 (2)	0.8223 (4)	0.65146 (17)	0.0270 (6)
C44	0.1767 (3)	0.9793 (4)	0.67206 (18)	0.0304 (6)
C45	0.3009 (2)	0.9244 (4)	0.65707 (17)	0.0283 (6)
C46	0.2824 (2)	0.8508 (3)	0.56422 (16)	0.0252 (6)
C47	0.0930 (3)	0.6881 (4)	0.38227 (16)	0.0304 (6)
H1	0.5450	0.0975	0.5763	0.023*
H6A	0.1714	0.1790	0.2459	0.031*
H6B	0.2750	0.0456	0.2734	0.031*
H3	0.4114	0.5397	0.6387	0.025*
H41	0.2269	0.5970	0.5913	0.026*
H42A	0.0302	0.8461	0.5149	0.031*
H42B	0.0097	0.6454	0.5475	0.031*
H43A	0.0035	0.8641	0.6579	0.032*
H43B	0.1142	0.7229	0.6942	0.032*
H44A	0.1900	1.0171	0.7340	0.037*
H44B	0.1422	1.0842	0.6340	0.037*
H45A	0.3564	1.0312	0.6661	0.034*
H45B	0.3406	0.8303	0.7004	0.034*
H46A	0.2502	0.9487	0.5211	0.030*
H46B	0.3631	0.8108	0.5570	0.030*
H47A	0.0090	0.6475	0.3794	0.046*
H47B	0.1145	0.6490	0.3291	0.046*
H47C	0.0971	0.8208	0.3865	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0215 (11)	0.0182 (10)	0.0164 (10)	0.0054 (8)	0.0025 (8)	−0.0021 (8)
N2	0.0215 (11)	0.0222 (11)	0.0185 (10)	0.0012 (9)	0.0032 (8)	−0.0046 (9)
N5	0.0177 (10)	0.0187 (10)	0.0189 (10)	0.0012 (8)	0.0038 (8)	−0.0003 (8)
N7	0.0176 (10)	0.0160 (10)	0.0162 (10)	0.0031 (8)	0.0024 (8)	−0.0005 (8)
N4	0.0240 (11)	0.0181 (11)	0.0204 (11)	0.0063 (8)	0.0056 (9)	0.0004 (8)
N6	0.0249 (12)	0.0274 (12)	0.0209 (11)	0.0109 (9)	−0.0014 (9)	−0.0048 (9)
C3	0.0240 (13)	0.0176 (12)	0.0208 (12)	0.0000 (10)	0.0060 (10)	−0.0028 (10)
C3A	0.0191 (12)	0.0153 (11)	0.0179 (12)	0.0014 (9)	0.0063 (10)	0.0001 (9)
C4	0.0188 (12)	0.0161 (12)	0.0206 (12)	0.0008 (9)	0.0083 (10)	0.0027 (10)
C6	0.0182 (12)	0.0170 (12)	0.0163 (12)	0.0000 (9)	0.0041 (9)	0.0003 (10)
C7A	0.0146 (11)	0.0166 (11)	0.0155 (11)	−0.0006 (9)	0.0030 (9)	0.0029 (9)
C41	0.0246 (13)	0.0194 (12)	0.0214 (12)	0.0061 (10)	0.0075 (10)	0.0010 (10)
C42	0.0258 (13)	0.0225 (13)	0.0292 (14)	0.0011 (11)	0.0098 (11)	−0.0011 (11)
C43	0.0264 (14)	0.0274 (14)	0.0304 (14)	0.0022 (11)	0.0131 (11)	−0.0041 (11)
C44	0.0357 (16)	0.0288 (14)	0.0293 (15)	0.0015 (12)	0.0130 (12)	−0.0085 (12)
C45	0.0283 (14)	0.0269 (14)	0.0312 (14)	−0.0045 (11)	0.0110 (12)	−0.0059 (12)
C46	0.0276 (14)	0.0234 (13)	0.0273 (13)	0.0004 (11)	0.0122 (11)	0.0002 (11)
C47	0.0346 (16)	0.0277 (14)	0.0264 (14)	0.0152 (12)	0.0043 (12)	0.0040 (11)

Geometric parameters (Å, º)

N1—C7A	1.344 (3)	C41—C42	1.535 (3)
N1—N2	1.373 (3)	C41—H41	1.00
N1—H1	0.86	C42—C43	1.531 (3)
N2—C3	1.316 (3)	C42—H42A	0.99
N5—C4	1.347 (3)	C42—H42B	0.99
N5—C6	1.354 (3)	C43—C44	1.528 (4)
N7—C6	1.343 (3)	C43—H43A	0.99
N7—C7A	1.350 (3)	C43—H43B	0.99
N4—C4	1.356 (3)	C44—C45	1.533 (4)
N4—C47	1.463 (3)	C44—H44A	0.99
N4—C41	1.467 (3)	C44—H44B	0.99
N6—C6	1.347 (3)	C45—C46	1.525 (3)
N6—H6A	0.86	C45—H45A	0.99
N6—H6B	0.86	C45—H45B	0.99
C3—C3A	1.429 (3)	C46—H46A	0.99
C3—H3	0.95	C46—H46B	0.99
C3A—C7A	1.397 (3)	C47—H47A	0.98
C3A—C4	1.429 (3)	C47—H47B	0.98
C41—C46	1.523 (3)	C47—H47C	0.98
C7A—N1—N2	111.39 (19)	C41—C42—H42A	109.7
C7A—N1—H1	128.8	C43—C42—H42B	109.7
N2—N1—H1	119.1	C41—C42—H42B	109.7
C3—N2—N1	105.69 (18)	H42A—C42—H42B	108.2
C4—N5—C6	119.0 (2)	C44—C43—C42	111.5 (2)
C6—N7—C7A	111.89 (19)	C44—C43—H43A	109.3
C4—N4—C47	120.0 (2)	C42—C43—H43A	109.3
C4—N4—C41	121.34 (19)	C44—C43—H43B	109.3
C47—N4—C41	118.70 (19)	C42—C43—H43B	109.3
C6—N6—H6A	120.0	H43A—C43—H43B	108.0
C6—N6—H6B	118.6	C43—C44—C45	111.2 (2)
H6A—N6—H6B	120.6	C43—C44—H44A	109.4
N2—C3—C3A	111.7 (2)	C45—C44—H44A	109.4
N2—C3—H3	124.2	C43—C44—H44B	109.4
C3A—C3—H3	124.2	C45—C44—H44B	109.4
C7A—C3A—C4	114.8 (2)	H44A—C44—H44B	108.0
C7A—C3A—C3	103.46 (19)	C46—C45—C44	110.8 (2)
C4—C3A—C3	141.7 (2)	C46—C45—H45A	109.5
N5—C4—N4	117.0 (2)	C44—C45—H45A	109.5
N5—C4—C3A	119.3 (2)	C46—C45—H45B	109.5
N4—C4—C3A	123.7 (2)	C44—C45—H45B	109.5
N7—C6—N6	117.0 (2)	H45A—C45—H45B	108.1
N7—C6—N5	127.5 (2)	C41—C46—C45	111.3 (2)
N6—C6—N5	115.5 (2)	C41—C46—H46A	109.4
N1—C7A—N7	124.8 (2)	C45—C46—H46A	109.4
N1—C7A—C3A	107.8 (2)	C41—C46—H46B	109.4
N7—C7A—C3A	127.4 (2)	C45—C46—H46B	109.4
N4—C41—C46	112.52 (19)	H46A—C46—H46B	108.0
N4—C41—C42	112.4 (2)	N4—C47—H47A	109.5
C46—C41—C42	110.2 (2)	N4—C47—H47B	109.5
N4—C41—H41	107.1	H47A—C47—H47B	109.5
C46—C41—H41	107.1	N4—C47—H47C	109.5
C42—C41—H41	107.1	H47A—C47—H47C	109.5
C43—C42—C41	110.0 (2)	H47B—C47—H47C	109.5
C43—C42—H42A	109.7
C7A—N1—N2—C3	−0.8 (3)	N2—N1—C7A—C3A	−0.2 (3)
N1—N2—C3—C3A	1.5 (3)	C6—N7—C7A—N1	−177.6 (2)
N2—C3—C3A—C7A	−1.5 (3)	C6—N7—C7A—C3A	1.6 (3)
N2—C3—C3A—C4	−178.9 (3)	C4—C3A—C7A—N1	179.2 (2)
C6—N5—C4—N4	−176.9 (2)	C3—C3A—C7A—N1	1.0 (2)
C6—N5—C4—C3A	3.1 (3)	C4—C3A—C7A—N7	−0.1 (3)
C47—N4—C4—N5	−11.6 (3)	C3—C3A—C7A—N7	−178.4 (2)
C41—N4—C4—N5	168.7 (2)	C4—N4—C41—C46	94.9 (3)
C47—N4—C4—C3A	168.4 (2)	C47—N4—C41—C46	−84.8 (3)
C41—N4—C4—C3A	−11.2 (3)	C4—N4—C41—C42	−140.0 (2)
C7A—C3A—C4—N5	−2.3 (3)	C47—N4—C41—C42	40.4 (3)
C3—C3A—C4—N5	174.9 (3)	N4—C41—C42—C43	175.7 (2)
C7A—C3A—C4—N4	177.7 (2)	C46—C41—C42—C43	−57.9 (3)
C3—C3A—C4—N4	−5.1 (5)	C41—C42—C43—C44	56.8 (3)
C7A—N7—C6—N6	179.5 (2)	C42—C43—C44—C45	−55.3 (3)
C7A—N7—C6—N5	−0.7 (3)	C43—C44—C45—C46	54.5 (3)
C4—N5—C6—N7	−1.6 (4)	N4—C41—C46—C45	−175.4 (2)
C4—N5—C6—N6	178.2 (2)	C42—C41—C46—C45	58.3 (3)
N2—N1—C7A—N7	179.2 (2)	C44—C45—C46—C41	−56.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N7^i	0.86	2.01	2.858 (3)	170
N6—H6A···N2^ii	0.86	2.13	2.959 (3)	161
N6—H6B···N5^iii	0.86	2.65	3.289 (3)	133

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2.

(III) N⁴-(3-Chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

Crystal data

C11H9ClN6	F(000) = 536
Mr = 260.69	Dx = 1.580 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2515 reflections
a = 11.1960 (8) Å	θ = 3.1–27.5°
b = 8.5040 (8) Å	µ = 0.34 mm^−1
c = 13.3815 (12) Å	T = 120 K
β = 120.674 (5)°	Lath, colourless
V = 1095.80 (16) Å^3	0.55 × 0.21 × 0.10 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2515 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1452 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.108
ϕ & ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −14→14
Tmin = 0.836, Tmax = 0.967	k = −11→11
26526 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.183	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0954P)^2 + 0.4665P] where P = (Fo^2 + 2Fc^2)/3
2515 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl43	0.94145 (10)	0.08799 (10)	0.86327 (7)	0.0304 (3)
N1	0.4781 (3)	0.8769 (3)	0.3832 (2)	0.0227 (7)
N2	0.4385 (3)	0.8045 (3)	0.2788 (2)	0.0237 (7)
N4	0.6910 (3)	0.3905 (3)	0.4744 (2)	0.0216 (7)
N5	0.7278 (3)	0.5627 (3)	0.6231 (2)	0.0212 (7)
N6	0.7696 (3)	0.7259 (4)	0.7724 (2)	0.0299 (8)
N7	0.6187 (3)	0.8196 (3)	0.5878 (2)	0.0218 (7)
C3	0.5002 (3)	0.6654 (4)	0.3064 (3)	0.0230 (8)
C3A	0.5801 (3)	0.6442 (4)	0.4277 (3)	0.0203 (7)
C4	0.6675 (3)	0.5298 (4)	0.5100 (3)	0.0194 (7)
C6	0.7025 (3)	0.7030 (4)	0.6557 (3)	0.0209 (7)
C7A	0.5619 (3)	0.7830 (4)	0.4740 (3)	0.0212 (8)
C41	0.7684 (3)	0.2593 (4)	0.5412 (3)	0.0201 (7)
C42	0.8109 (3)	0.2404 (4)	0.6580 (3)	0.0212 (8)
C43	0.8862 (3)	0.1070 (4)	0.7159 (3)	0.0229 (8)
C44	0.9164 (3)	−0.0108 (4)	0.6613 (3)	0.0238 (8)
C45	0.8698 (3)	0.0073 (4)	0.5435 (3)	0.0257 (8)
C46	0.7984 (4)	0.1417 (4)	0.4845 (3)	0.0238 (8)
H1	0.4404	0.9662	0.3803	0.027*
H4	0.6511	0.3768	0.4005	0.026*
H6A	0.8342	0.6569	0.8070	0.036*
H6B	0.7850	0.8183	0.8025	0.036*
H3	0.4916	0.5892	0.2512	0.028*
H42	0.7888	0.3174	0.6976	0.025*
H44	0.9674	−0.1014	0.7027	0.029*
H45	0.8871	−0.0731	0.5032	0.031*
H46	0.7697	0.1538	0.4048	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl43	0.0392 (6)	0.0291 (5)	0.0193 (5)	0.0039 (4)	0.0122 (4)	0.0030 (4)
N1	0.0236 (15)	0.0241 (16)	0.0195 (15)	0.0009 (12)	0.0104 (13)	0.0003 (12)
N2	0.0269 (16)	0.0271 (17)	0.0168 (15)	0.0019 (13)	0.0108 (13)	0.0008 (12)
N4	0.0263 (16)	0.0217 (16)	0.0126 (14)	0.0027 (12)	0.0069 (12)	0.0000 (11)
N5	0.0234 (15)	0.0201 (15)	0.0173 (14)	0.0014 (12)	0.0084 (12)	−0.0003 (12)
N6	0.0392 (19)	0.0262 (17)	0.0184 (16)	0.0044 (14)	0.0105 (14)	−0.0027 (13)
N7	0.0235 (15)	0.0227 (16)	0.0161 (14)	0.0025 (12)	0.0079 (12)	0.0001 (12)
C3	0.0257 (19)	0.0227 (19)	0.0177 (17)	0.0022 (15)	0.0089 (15)	−0.0026 (15)
C3A	0.0206 (17)	0.0203 (17)	0.0167 (17)	−0.0008 (14)	0.0071 (14)	0.0001 (14)
C4	0.0194 (17)	0.0194 (18)	0.0210 (17)	−0.0012 (14)	0.0114 (14)	0.0000 (14)
C6	0.0220 (18)	0.0203 (18)	0.0186 (17)	0.0004 (15)	0.0092 (15)	0.0000 (14)
C7A	0.0199 (18)	0.0212 (19)	0.0220 (18)	0.0008 (14)	0.0103 (15)	0.0006 (14)
C41	0.0161 (16)	0.0202 (18)	0.0213 (17)	−0.0043 (14)	0.0077 (14)	−0.0014 (14)
C42	0.0213 (18)	0.0219 (18)	0.0204 (17)	−0.0021 (14)	0.0106 (15)	−0.0041 (14)
C43	0.0220 (18)	0.025 (2)	0.0175 (17)	−0.0028 (15)	0.0070 (15)	0.0004 (14)
C44	0.0256 (18)	0.0175 (18)	0.0266 (19)	0.0041 (15)	0.0121 (16)	0.0027 (15)
C45	0.0284 (19)	0.0215 (19)	0.0284 (19)	0.0018 (16)	0.0153 (16)	−0.0026 (16)
C46	0.0286 (19)	0.0237 (19)	0.0179 (18)	0.0006 (15)	0.0111 (15)	−0.0029 (15)

Geometric parameters (Å, º)

Cl43—C43	1.748 (3)	C3—C3A	1.408 (4)
N1—C7A	1.354 (4)	C3—H3	0.95
N1—N2	1.377 (4)	C3A—C7A	1.395 (5)
N1—H1	0.86	C3A—C4	1.421 (5)
N2—C3	1.324 (4)	C41—C42	1.392 (4)
N4—C4	1.352 (4)	C41—C46	1.396 (5)
N4—C41	1.415 (4)	C42—C43	1.390 (5)
N4—H4	0.86	C42—H42	0.95
N5—C4	1.334 (4)	C43—C44	1.380 (5)
N5—C6	1.349 (4)	C44—C45	1.394 (5)
N6—C6	1.358 (4)	C44—H44	0.95
N6—H6A	0.8601	C45—C46	1.387 (5)
N6—H6B	0.86	C45—H45	0.95
N7—C6	1.349 (4)	C46—H46	0.95
N7—C7A	1.353 (4)
C7A—N1—N2	111.3 (3)	N5—C6—N6	114.5 (3)
C7A—N1—H1	131.4	N7—C7A—N1	125.9 (3)
N2—N1—H1	116.9	N7—C7A—C3A	127.1 (3)
C3—N2—N1	105.3 (3)	N1—C7A—C3A	107.0 (3)
C4—N4—C41	129.4 (3)	C42—C41—C46	119.2 (3)
C4—N4—H4	116.3	C42—C41—N4	123.3 (3)
C41—N4—H4	114.3	C46—C41—N4	117.4 (3)
C4—N5—C6	118.9 (3)	C43—C42—C41	118.8 (3)
C6—N6—H6A	110.0	C43—C42—H42	120.6
C6—N6—H6B	122.1	C41—C42—H42	120.6
H6A—N6—H6B	117.3	C44—C43—C42	122.8 (3)
C6—N7—C7A	110.8 (3)	C44—C43—Cl43	119.3 (3)
N2—C3—C3A	111.7 (3)	C42—C43—Cl43	117.9 (3)
N2—C3—H3	124.1	C43—C44—C45	117.8 (3)
C3A—C3—H3	124.1	C43—C44—H44	121.1
C7A—C3A—C3	104.6 (3)	C45—C44—H44	121.1
C7A—C3A—C4	115.7 (3)	C46—C45—C44	120.6 (3)
C3—C3A—C4	139.7 (3)	C46—C45—H45	119.7
N5—C4—N4	120.4 (3)	C44—C45—H45	119.7
N5—C4—C3A	119.1 (3)	C45—C46—C41	120.7 (3)
N4—C4—C3A	120.5 (3)	C45—C46—H46	119.7
N7—C6—N5	128.3 (3)	C41—C46—H46	119.7
N7—C6—N6	117.2 (3)
C7A—N1—N2—C3	−0.6 (4)	N2—N1—C7A—N7	179.8 (3)
N1—N2—C3—C3A	0.1 (4)	N2—N1—C7A—C3A	1.0 (4)
N2—C3—C3A—C7A	0.5 (4)	C3—C3A—C7A—N7	−179.7 (3)
N2—C3—C3A—C4	−179.5 (4)	C4—C3A—C7A—N7	0.3 (5)
C6—N5—C4—N4	179.8 (3)	C3—C3A—C7A—N1	−0.8 (4)
C6—N5—C4—C3A	0.8 (5)	C4—C3A—C7A—N1	179.1 (3)
C41—N4—C4—N5	4.3 (5)	C4—N4—C41—C42	14.2 (5)
C41—N4—C4—C3A	−176.7 (3)	C4—N4—C41—C46	−168.0 (3)
C7A—C3A—C4—N5	−1.6 (5)	C46—C41—C42—C43	2.1 (5)
C3—C3A—C4—N5	178.4 (4)	N4—C41—C42—C43	179.8 (3)
C7A—C3A—C4—N4	179.4 (3)	C41—C42—C43—C44	−2.4 (5)
C3—C3A—C4—N4	−0.6 (6)	C41—C42—C43—Cl43	178.7 (2)
C7A—N7—C6—N5	−2.8 (5)	C42—C43—C44—C45	0.6 (5)
C7A—N7—C6—N6	178.3 (3)	Cl43—C43—C44—C45	179.5 (3)
C4—N5—C6—N7	1.7 (5)	C43—C44—C45—C46	1.6 (5)
C4—N5—C6—N6	−179.4 (3)	C44—C45—C46—C41	−1.8 (5)
C6—N7—C7A—N1	−176.9 (3)	C42—C41—C46—C45	0.0 (5)
C6—N7—C7A—C3A	1.7 (5)	N4—C41—C46—C45	−177.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N7^i	0.86	2.06	2.901 (4)	167
N4—H4···N2^ii	0.86	2.17	3.017 (4)	171
N6—H6B···Cl43^iii	0.86	2.74	3.504 (3)	148

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, y−1/2, −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

Crystal data

C11H17N7O	F(000) = 1120
Mr = 263.32	Dx = 1.393 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2877 reflections
a = 7.0297 (9) Å	θ = 3.0–27.5°
b = 13.859 (3) Å	µ = 0.10 mm^−1
c = 25.766 (6) Å	T = 120 K
V = 2510.2 (9) Å^3	Lath, colourless
Z = 8	0.20 × 0.10 × 0.08 mm

Data collection

Bruker-Nonius KappaCCD diffractometer	2877 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1479 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.171
ϕ & ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −9→9
Tmin = 0.985, Tmax = 0.992	k = −18→18
59170 measured reflections	l = −33→33

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.224	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.1298P)^2] where P = (Fo^2 + 2Fc^2)/3
2877 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O4	0.0758 (3)	0.70074 (16)	0.30495 (9)	0.0357 (6)
N1	1.0456 (4)	0.24499 (18)	0.33828 (10)	0.0282 (7)
N2	0.9778 (4)	0.28387 (19)	0.29284 (10)	0.0295 (7)
N5	0.6912 (3)	0.34275 (17)	0.44779 (10)	0.0266 (6)
N6	0.8470 (4)	0.25795 (19)	0.51087 (10)	0.0314 (7)
N7	0.9701 (4)	0.24650 (17)	0.42870 (10)	0.0266 (6)
N41	0.5186 (4)	0.42918 (18)	0.38860 (10)	0.0275 (6)
N44	0.2016 (4)	0.55466 (18)	0.37198 (10)	0.0280 (7)
C3	0.8265 (4)	0.3342 (2)	0.30558 (12)	0.0282 (8)
C3A	0.7919 (4)	0.3303 (2)	0.35955 (12)	0.0247 (7)
C4	0.6661 (4)	0.3680 (2)	0.39809 (12)	0.0250 (7)
C6	0.8372 (4)	0.2819 (2)	0.46053 (13)	0.0279 (8)
C7A	0.9382 (4)	0.2714 (2)	0.37915 (12)	0.0255 (8)
C11	−0.0507 (4)	0.6231 (2)	0.31542 (12)	0.0304 (8)
C18	−0.0004 (4)	0.5813 (2)	0.36710 (12)	0.0288 (8)
C42	0.4439 (4)	0.4902 (2)	0.43035 (13)	0.0296 (8)
C43	0.2361 (5)	0.5107 (2)	0.42264 (12)	0.0298 (8)
C45	0.2620 (4)	0.4865 (2)	0.33192 (12)	0.0286 (8)
C46	0.4717 (4)	0.4626 (2)	0.33674 (12)	0.0308 (8)
H4	0.0477	0.7182	0.2755	0.054*
H1	1.1447	0.2086	0.3373	0.034*
H6B	0.9372	0.2227	0.5230	0.038*
H6A	0.7532	0.2729	0.5307	0.038*
H3	0.7501	0.3688	0.2816	0.034*
H11A	−0.0391	0.5731	0.2881	0.036*
H11B	−0.1837	0.6466	0.3158	0.036*
H18A	−0.0321	0.6288	0.3944	0.035*
H18B	−0.0792	0.5231	0.3731	0.035*
H42A	0.5152	0.5517	0.4312	0.035*
H42B	0.4626	0.4573	0.4641	0.035*
H43A	0.1632	0.4498	0.4253	0.036*
H43B	0.1911	0.5547	0.4503	0.036*
H45A	0.2372	0.5147	0.2973	0.034*
H45B	0.1865	0.4265	0.3350	0.034*
H46A	0.5051	0.4119	0.3112	0.037*
H46B	0.5479	0.5207	0.3286	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0350 (14)	0.0362 (14)	0.0358 (14)	−0.0073 (10)	−0.0050 (11)	0.0122 (10)
N1	0.0291 (14)	0.0295 (14)	0.0262 (15)	0.0059 (12)	−0.0005 (12)	−0.0009 (12)
N2	0.0319 (15)	0.0337 (15)	0.0230 (15)	0.0003 (13)	−0.0022 (12)	−0.0020 (12)
N5	0.0300 (15)	0.0237 (13)	0.0260 (15)	0.0022 (11)	−0.0006 (11)	0.0030 (11)
N6	0.0310 (15)	0.0379 (16)	0.0254 (16)	0.0082 (13)	0.0033 (12)	0.0075 (13)
N7	0.0274 (14)	0.0258 (14)	0.0264 (15)	0.0020 (12)	0.0003 (12)	0.0006 (11)
N41	0.0315 (15)	0.0278 (15)	0.0231 (15)	0.0042 (12)	−0.0008 (11)	0.0014 (11)
N44	0.0310 (15)	0.0258 (14)	0.0271 (16)	0.0037 (12)	−0.0011 (11)	−0.0003 (11)
C3	0.0292 (17)	0.0277 (17)	0.0276 (19)	0.0015 (15)	−0.0019 (14)	0.0007 (14)
C3A	0.0252 (16)	0.0261 (16)	0.0228 (17)	−0.0001 (14)	−0.0012 (13)	0.0009 (13)
C4	0.0263 (16)	0.0227 (16)	0.0259 (18)	−0.0044 (14)	0.0012 (13)	0.0001 (14)
C6	0.0283 (17)	0.0267 (16)	0.0287 (19)	−0.0025 (14)	0.0010 (14)	−0.0011 (14)
C7A	0.0272 (17)	0.0248 (17)	0.0245 (18)	−0.0037 (13)	0.0013 (14)	−0.0019 (13)
C11	0.0269 (17)	0.0245 (17)	0.040 (2)	−0.0012 (14)	0.0002 (15)	0.0028 (15)
C18	0.0291 (18)	0.0248 (17)	0.033 (2)	0.0002 (14)	0.0006 (14)	0.0039 (14)
C42	0.0345 (18)	0.0280 (17)	0.0263 (18)	0.0053 (15)	−0.0020 (14)	−0.0021 (14)
C43	0.0392 (19)	0.0273 (17)	0.0227 (18)	0.0031 (15)	0.0016 (14)	0.0006 (14)
C45	0.0318 (18)	0.0295 (17)	0.0245 (18)	−0.0009 (15)	0.0008 (14)	−0.0018 (14)
C46	0.0378 (19)	0.0334 (18)	0.0212 (18)	0.0072 (15)	−0.0010 (14)	0.0008 (14)

Geometric parameters (Å, º)

O4—C11	1.422 (4)	C3—C3A	1.413 (4)
O4—H4	0.82	C3—H3	0.95
N1—C7A	1.346 (4)	C3A—C7A	1.407 (4)
N1—N2	1.374 (3)	C3A—C4	1.429 (4)
N1—H1	0.86	C11—C18	1.495 (4)
N2—C3	1.313 (4)	C11—H11A	0.99
N5—C4	1.339 (4)	C11—H11B	0.99
N5—C6	1.368 (4)	C18—H18A	0.99
N6—C6	1.341 (4)	C18—H18B	0.99
N6—H6B	0.86	C42—C43	1.502 (4)
N6—H6A	0.86	C42—H42A	0.99
N7—C6	1.337 (4)	C42—H42B	0.99
N7—C7A	1.341 (4)	C43—H43A	0.99
N41—C4	1.361 (4)	C43—H43B	0.99
N41—C46	1.452 (4)	C45—C46	1.516 (4)
N41—C42	1.465 (4)	C45—H45A	0.99
N44—C43	1.461 (4)	C45—H45B	0.99
N44—C45	1.462 (4)	C46—H46A	0.99
N44—C18	1.472 (4)	C46—H46B	0.99
C11—O4—H4	104.3	O4—C11—H11B	110.0
C7A—N1—N2	111.4 (3)	C18—C11—H11B	110.0
C7A—N1—H1	129.5	H11A—C11—H11B	108.4
N2—N1—H1	119.1	N44—C18—C11	113.7 (3)
C3—N2—N1	106.0 (3)	N44—C18—H18A	108.8
C4—N5—C6	119.3 (3)	C11—C18—H18A	108.8
C6—N6—H6B	122.0	N44—C18—H18B	108.8
C6—N6—H6A	118.5	C11—C18—H18B	108.8
H6B—N6—H6A	119.1	H18A—C18—H18B	107.7
C6—N7—C7A	111.9 (3)	N41—C42—C43	111.2 (3)
C4—N41—C46	122.5 (3)	N41—C42—H42A	109.4
C4—N41—C42	120.0 (3)	C43—C42—H42A	109.4
C46—N41—C42	114.2 (2)	N41—C42—H42B	109.4
C43—N44—C45	108.2 (2)	C43—C42—H42B	109.4
C43—N44—C18	109.9 (2)	H42A—C42—H42B	108.0
C45—N44—C18	112.4 (2)	N44—C43—C42	111.0 (3)
N2—C3—C3A	111.4 (3)	N44—C43—H43A	109.4
N2—C3—H3	124.3	C42—C43—H43A	109.4
C3A—C3—H3	124.3	N44—C43—H43B	109.4
C7A—C3A—C3	104.5 (3)	C42—C43—H43B	109.4
C7A—C3A—C4	114.5 (3)	H43A—C43—H43B	108.0
C3—C3A—C4	141.0 (3)	N44—C45—C46	111.5 (3)
N5—C4—N41	115.8 (3)	N44—C45—H45A	109.3
N5—C4—C3A	119.2 (3)	C46—C45—H45A	109.3
N41—C4—C3A	125.0 (3)	N44—C45—H45B	109.3
N7—C6—N6	117.8 (3)	C46—C45—H45B	109.3
N7—C6—N5	127.1 (3)	H45A—C45—H45B	108.0
N6—C6—N5	115.0 (3)	N41—C46—C45	111.5 (3)
N7—C7A—N1	125.5 (3)	N41—C46—H46A	109.3
N7—C7A—C3A	127.8 (3)	C45—C46—H46A	109.3
N1—C7A—C3A	106.7 (3)	N41—C46—H46B	109.3
O4—C11—C18	108.3 (2)	C45—C46—H46B	109.3
O4—C11—H11A	110.0	H46A—C46—H46B	108.0
C18—C11—H11A	110.0
C7A—N1—N2—C3	−0.4 (3)	N2—N1—C7A—N7	−178.7 (3)
N1—N2—C3—C3A	0.4 (3)	N2—N1—C7A—C3A	0.2 (3)
N2—C3—C3A—C7A	−0.3 (3)	C3—C3A—C7A—N7	178.9 (3)
N2—C3—C3A—C4	177.0 (4)	C4—C3A—C7A—N7	0.8 (5)
C6—N5—C4—N41	−179.6 (3)	C3—C3A—C7A—N1	0.0 (3)
C6—N5—C4—C3A	0.3 (4)	C4—C3A—C7A—N1	−178.1 (3)
C46—N41—C4—N5	−179.4 (3)	C43—N44—C18—C11	−177.5 (3)
C42—N41—C4—N5	22.2 (4)	C45—N44—C18—C11	−56.9 (3)
C46—N41—C4—C3A	0.7 (5)	O4—C11—C18—N44	−53.0 (3)
C42—N41—C4—C3A	−157.7 (3)	C4—N41—C42—C43	−150.4 (3)
C7A—C3A—C4—N5	−2.3 (4)	C46—N41—C42—C43	49.6 (4)
C3—C3A—C4—N5	−179.4 (4)	C45—N44—C43—C42	61.4 (3)
C7A—C3A—C4—N41	177.6 (3)	C18—N44—C43—C42	−175.4 (2)
C3—C3A—C4—N41	0.5 (6)	N41—C42—C43—N44	−56.1 (3)
C7A—N7—C6—N6	176.5 (3)	C43—N44—C45—C46	−60.1 (3)
C7A—N7—C6—N5	−5.0 (4)	C18—N44—C45—C46	178.3 (2)
C4—N5—C6—N7	3.8 (5)	C4—N41—C46—C45	152.2 (3)
C4—N5—C6—N6	−177.7 (3)	C42—N41—C46—C45	−48.3 (3)
C6—N7—C7A—N1	−178.7 (3)	N44—C45—C46—N41	53.8 (3)
C6—N7—C7A—C3A	2.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4^i	0.86	2.14	2.863 (3)	142
N1—H1···N44^i	0.86	2.55	3.297 (4)	145
N6—H6A···N7^ii	0.86	2.26	3.074 (4)	157
N6—H6B···N5^iii	0.86	2.14	2.990 (4)	170
O4—H4···N2^iv	0.82	1.99	2.796 (3)	167

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x−1/2, −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

Crystal data

C13H14N6·H2O	F(000) = 1152
Mr = 272.32	Dx = 1.363 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3046 reflections
a = 16.5577 (12) Å	θ = 3.3–27.5°
b = 8.6833 (3) Å	µ = 0.09 mm^−1
c = 18.4640 (13) Å	T = 120 K
V = 2654.7 (3) Å^3	Block, colourless
Z = 8	0.37 × 0.24 × 0.23 mm

Data collection

Bruker-Nonius KappaCCD diffractometer	3046 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2146 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
ϕ & ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −21→21
Tmin = 0.969, Tmax = 0.979	k = −11→11
61337 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0501P)^2 + 1.7622P] where P = (Fo^2 + 2Fc^2)/3
3046 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.45042 (9)	0.75734 (17)	0.43453 (8)	0.0197 (3)
N2	0.52896 (9)	0.76445 (17)	0.40995 (8)	0.0214 (3)
N4	0.50382 (8)	0.26531 (16)	0.34624 (8)	0.0201 (3)
N5	0.38597 (8)	0.31554 (16)	0.40814 (8)	0.0184 (3)
N6	0.26251 (9)	0.36047 (17)	0.46060 (8)	0.0246 (4)
N7	0.34479 (9)	0.57044 (16)	0.44702 (8)	0.0193 (3)
C3	0.54657 (11)	0.6244 (2)	0.38710 (9)	0.0206 (4)
C3A	0.48052 (10)	0.52248 (19)	0.39677 (9)	0.0180 (4)
C4	0.45786 (10)	0.36621 (19)	0.38387 (9)	0.0174 (4)
C6	0.33342 (10)	0.4186 (2)	0.43784 (9)	0.0184 (4)
C7A	0.41980 (10)	0.61376 (19)	0.42747 (9)	0.0179 (4)
C41	0.58589 (10)	0.29925 (19)	0.32738 (9)	0.0190 (4)
C42	0.64458 (11)	0.3072 (2)	0.38076 (10)	0.0233 (4)
C43	0.72371 (11)	0.3429 (2)	0.36250 (10)	0.0244 (4)
C44	0.74590 (11)	0.3677 (2)	0.29099 (10)	0.0226 (4)
C45	0.68651 (11)	0.3531 (2)	0.23748 (10)	0.0237 (4)
C46	0.60733 (11)	0.3189 (2)	0.25528 (10)	0.0208 (4)
C47	0.83125 (11)	0.4100 (2)	0.27156 (11)	0.0300 (4)
C48	0.47283 (11)	0.1145 (2)	0.32465 (10)	0.0239 (4)
O1	0.61376 (7)	0.96207 (14)	0.50869 (7)	0.0222 (3)
H1	0.4288	0.8396	0.4519	0.024*
H6B	0.2263	0.4207	0.4783	0.030*
H6A	0.2502	0.2655	0.4530	0.030*
H3	0.5971	0.5956	0.3668	0.025*
H42	0.6306	0.2882	0.4299	0.028*
H43	0.7633	0.3505	0.3996	0.029*
H45	0.7008	0.3670	0.1881	0.028*
H46	0.5678	0.3088	0.2183	0.025*
H47A	0.8356	0.4230	0.2190	0.036*	0.50
H47B	0.8459	0.5067	0.2957	0.036*	0.50
H47C	0.8679	0.3281	0.2874	0.036*	0.50
H47D	0.8640	0.4155	0.3157	0.036*	0.50
H47E	0.8537	0.3318	0.2390	0.036*	0.50
H47F	0.8317	0.5104	0.2473	0.036*	0.50
H48A	0.4137	0.1172	0.3239	0.036*
H48B	0.4910	0.0365	0.3594	0.036*
H48C	0.4930	0.0887	0.2763	0.036*
H1A	0.5941	0.9227	0.4723	0.033*
H1B	0.6172	0.8897	0.5371	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0203 (7)	0.0155 (7)	0.0233 (7)	−0.0006 (6)	0.0014 (6)	−0.0026 (6)
N2	0.0186 (7)	0.0210 (8)	0.0247 (8)	−0.0021 (6)	0.0013 (6)	−0.0006 (6)
N4	0.0184 (7)	0.0163 (7)	0.0256 (8)	−0.0006 (6)	0.0017 (6)	−0.0039 (6)
N5	0.0177 (7)	0.0166 (7)	0.0210 (7)	0.0007 (6)	0.0010 (6)	−0.0015 (6)
N6	0.0207 (8)	0.0180 (7)	0.0351 (9)	−0.0008 (6)	0.0067 (7)	−0.0033 (6)
N7	0.0201 (7)	0.0160 (7)	0.0219 (7)	−0.0006 (6)	0.0012 (6)	−0.0016 (6)
C3	0.0211 (9)	0.0185 (9)	0.0221 (9)	−0.0008 (7)	0.0004 (7)	−0.0013 (7)
C3A	0.0197 (8)	0.0180 (8)	0.0163 (8)	0.0007 (7)	−0.0005 (7)	−0.0016 (6)
C4	0.0187 (8)	0.0177 (8)	0.0157 (8)	0.0017 (7)	−0.0018 (7)	−0.0007 (6)
C6	0.0186 (8)	0.0184 (8)	0.0183 (8)	0.0004 (7)	−0.0008 (7)	−0.0001 (7)
C7A	0.0200 (8)	0.0165 (8)	0.0171 (8)	−0.0006 (7)	−0.0007 (7)	−0.0004 (6)
C41	0.0198 (8)	0.0143 (8)	0.0231 (9)	0.0020 (7)	0.0017 (7)	−0.0024 (7)
C42	0.0258 (10)	0.0259 (9)	0.0181 (9)	0.0016 (8)	0.0012 (7)	−0.0014 (7)
C43	0.0224 (9)	0.0275 (10)	0.0234 (9)	−0.0004 (8)	−0.0036 (7)	−0.0023 (8)
C44	0.0226 (9)	0.0193 (9)	0.0259 (9)	0.0022 (7)	0.0030 (8)	0.0002 (7)
C45	0.0271 (10)	0.0236 (9)	0.0205 (9)	0.0018 (8)	0.0037 (7)	0.0028 (7)
C46	0.0233 (9)	0.0185 (8)	0.0207 (9)	0.0013 (7)	−0.0036 (7)	0.0003 (7)
C47	0.0249 (10)	0.0319 (11)	0.0333 (11)	−0.0027 (8)	0.0026 (8)	0.0005 (9)
C48	0.0250 (9)	0.0168 (9)	0.0298 (10)	−0.0007 (7)	0.0036 (8)	−0.0053 (7)
O1	0.0247 (7)	0.0170 (6)	0.0248 (7)	−0.0018 (5)	−0.0028 (5)	−0.0012 (5)

Geometric parameters (Å, º)

N1—C7A	1.352 (2)	C42—C43	1.388 (3)
N1—N2	1.379 (2)	C42—H42	0.95
N1—H1	0.86	C43—C44	1.387 (3)
N2—C3	1.320 (2)	C43—H43	0.95
N4—C4	1.353 (2)	C44—C45	1.400 (3)
N4—C41	1.433 (2)	C44—C47	1.504 (3)
N4—C48	1.462 (2)	C45—C46	1.384 (2)
N5—C4	1.346 (2)	C45—H45	0.95
N5—C6	1.363 (2)	C46—H46	0.95
N6—C6	1.345 (2)	C47—H47A	0.98
N6—H6B	0.86	C47—H47B	0.9801
N6—H6A	0.86	C47—H47C	0.98
N7—C6	1.343 (2)	C47—H47D	0.9801
N7—C7A	1.347 (2)	C47—H47E	0.98
C3—C3A	1.418 (2)	C47—H47F	0.98
C3—H3	0.95	C48—H48A	0.98
C3A—C7A	1.400 (2)	C48—H48B	0.98
C3A—C4	1.428 (2)	C48—H48C	0.98
C41—C42	1.386 (2)	O1—H1A	0.82
C41—C46	1.388 (2)	O1—H1B	0.82
C7A—N1—N2	111.30 (14)	C43—C44—C47	120.93 (17)
C7A—N1—H1	130.2	C45—C44—C47	120.93 (17)
N2—N1—H1	118.5	C46—C45—C44	121.16 (17)
C3—N2—N1	105.81 (14)	C46—C45—H45	119.4
C4—N4—C41	121.67 (14)	C44—C45—H45	119.4
C4—N4—C48	121.52 (14)	C45—C46—C41	119.75 (16)
C41—N4—C48	116.79 (14)	C45—C46—H46	120.1
C4—N5—C6	118.94 (14)	C41—C46—H46	120.1
C6—N6—H6B	119.9	C44—C47—H47A	109.5
C6—N6—H6A	121.0	C44—C47—H47B	109.5
H6B—N6—H6A	118.7	H47A—C47—H47B	109.5
C6—N7—C7A	111.70 (14)	C44—C47—H47C	109.5
N2—C3—C3A	111.37 (15)	H47A—C47—H47C	109.5
N2—C3—H3	124.3	H47B—C47—H47C	109.5
C3A—C3—H3	124.3	C44—C47—H47D	109.5
C7A—C3A—C3	104.56 (15)	H47A—C47—H47D	141.1
C7A—C3A—C4	114.63 (15)	H47B—C47—H47D	56.3
C3—C3A—C4	140.78 (16)	H47C—C47—H47D	56.2
N5—C4—N4	117.18 (15)	C44—C47—H47E	109.5
N5—C4—C3A	119.18 (15)	H47A—C47—H47E	56.3
N4—C4—C3A	123.60 (15)	H47B—C47—H47E	141.1
N7—C6—N6	116.83 (15)	H47C—C47—H47E	56.3
N7—C6—N5	127.30 (16)	H47D—C47—H47E	109.5
N6—C6—N5	115.88 (15)	C44—C47—H47F	109.5
N7—C7A—N1	125.27 (15)	H47A—C47—H47F	56.2
N7—C7A—C3A	127.77 (15)	H47B—C47—H47F	56.3
N1—C7A—C3A	106.96 (15)	H47C—C47—H47F	141.1
C42—C41—C46	119.78 (16)	H47D—C47—H47F	109.5
C42—C41—N4	120.15 (16)	H47E—C47—H47F	109.5
C46—C41—N4	120.04 (16)	N4—C48—H48A	109.5
C41—C42—C43	120.02 (17)	N4—C48—H48B	109.5
C41—C42—H42	120.0	H48A—C48—H48B	109.5
C43—C42—H42	120.0	N4—C48—H48C	109.5
C44—C43—C42	121.06 (17)	H48A—C48—H48C	109.5
C44—C43—H43	119.5	H48B—C48—H48C	109.5
C42—C43—H43	119.5	H1A—O1—H1B	103.4
C43—C44—C45	118.14 (17)
C7A—N1—N2—C3	0.45 (19)	N2—N1—C7A—N7	179.65 (15)
N1—N2—C3—C3A	−0.54 (19)	N2—N1—C7A—C3A	−0.18 (19)
N2—C3—C3A—C7A	0.4 (2)	C3—C3A—C7A—N7	−179.97 (16)
N2—C3—C3A—C4	178.4 (2)	C4—C3A—C7A—N7	1.5 (3)
C6—N5—C4—N4	−171.45 (15)	C3—C3A—C7A—N1	−0.14 (18)
C6—N5—C4—C3A	6.6 (2)	C4—C3A—C7A—N1	−178.72 (14)
C41—N4—C4—N5	−170.51 (15)	C4—N4—C41—C42	68.7 (2)
C48—N4—C4—N5	7.7 (2)	C48—N4—C41—C42	−109.56 (19)
C41—N4—C4—C3A	11.6 (3)	C4—N4—C41—C46	−113.54 (19)
C48—N4—C4—C3A	−170.21 (16)	C48—N4—C41—C46	68.2 (2)
C7A—C3A—C4—N5	−6.8 (2)	C46—C41—C42—C43	3.5 (3)
C3—C3A—C4—N5	175.4 (2)	N4—C41—C42—C43	−178.80 (16)
C7A—C3A—C4—N4	171.10 (16)	C41—C42—C43—C44	−1.5 (3)
C3—C3A—C4—N4	−6.7 (3)	C42—C43—C44—C45	−1.1 (3)
C7A—N7—C6—N6	175.30 (15)	C42—C43—C44—C47	178.54 (17)
C7A—N7—C6—N5	−4.4 (2)	C43—C44—C45—C46	1.6 (3)
C4—N5—C6—N7	−0.7 (3)	C47—C44—C45—C46	−177.97 (17)
C4—N5—C6—N6	179.63 (15)	C44—C45—C46—C41	0.3 (3)
C6—N7—C7A—N1	−175.96 (16)	C42—C41—C46—C45	−2.9 (3)
C6—N7—C7A—C3A	3.8 (2)	N4—C41—C46—C45	179.36 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.82	2.09	2.871 (2)	158
O1—H1B···N5^i	0.82	2.05	2.858 (2)	168
N1—H1···O1^ii	0.86	2.00	2.857 (2)	176
N6—H6A···N7^iii	0.86	2.31	3.092 (2)	150
N6—H6B···O1^iv	0.86	2.14	2.960 (2)	160
C3—H3···Cg1	0.95	2.77	3.526 (2)	137

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) −x+1/2, y−1/2, z; (iv) x−1/2, −y+3/2, −z+1.

(VI) N⁴-Ethyl-N⁴-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine hemihydrate

Crystal data

2(C13H14N6)·H2O	F(000) = 1112
Mr = 526.62	Dx = 1.344 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2987 reflections
a = 17.642 (3) Å	θ = 3.2–27.5°
b = 18.278 (3) Å	µ = 0.09 mm^−1
c = 8.3034 (18) Å	T = 120 K
β = 103.512 (17)°	Plate, colourless
V = 2603.4 (9) Å^3	0.45 × 0.21 × 0.07 mm
Z = 4

Data collection

Bruker-Nonius KappaCCD diffractometer	2987 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1829 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
ϕ & ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −22→22
Tmin = 0.966, Tmax = 0.994	k = −23→23
32439 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.159	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0797P)^2 + 1.7517P] where P = (Fo^2 + 2Fc^2)/3
2987 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.30796 (10)	0.20876 (9)	0.1732 (2)	0.0295 (4)
N2	0.36958 (10)	0.18962 (10)	0.3008 (2)	0.0339 (4)
N5	0.11989 (9)	0.12919 (9)	0.30734 (19)	0.0262 (4)
N6	0.03910 (10)	0.17229 (10)	0.0707 (2)	0.0350 (5)
N7	0.16933 (9)	0.19546 (9)	0.1007 (2)	0.0282 (4)
N4	0.19919 (10)	0.07825 (9)	0.5426 (2)	0.0285 (4)
C3	0.33912 (12)	0.15355 (12)	0.4079 (3)	0.0315 (5)
C3A	0.25704 (11)	0.14876 (11)	0.3531 (2)	0.0265 (4)
C4	0.19126 (12)	0.11877 (10)	0.4028 (2)	0.0252 (4)
C6	0.11201 (12)	0.16586 (11)	0.1620 (2)	0.0266 (5)
C7A	0.24001 (11)	0.18529 (10)	0.2019 (2)	0.0257 (4)
C41	0.27459 (12)	0.07066 (11)	0.6528 (2)	0.0271 (5)
C42	0.30463 (12)	0.12715 (11)	0.7598 (2)	0.0308 (5)
C43	0.37934 (12)	0.12241 (12)	0.8584 (3)	0.0336 (5)
C44	0.42360 (13)	0.06039 (12)	0.8523 (3)	0.0349 (5)
C45	0.39276 (13)	0.00308 (12)	0.7483 (3)	0.0352 (5)
C46	0.31820 (12)	0.00788 (11)	0.6484 (3)	0.0314 (5)
C47	0.13308 (12)	0.04369 (12)	0.5922 (3)	0.0332 (5)
C48	0.11208 (14)	0.08256 (15)	0.7351 (3)	0.0478 (6)
O1	0.5000	0.25671 (11)	0.2500	0.0323 (5)
H1	0.3152	0.2360	0.0937	0.035*
H6A	0.0013	0.1562	0.1100	0.042*
H6B	0.0272	0.1935	−0.0245	0.042*
H3	0.3684	0.1334	0.5088	0.038*
H2	0.2738	0.1693	0.7655	0.037*
H43	0.4003	0.1616	0.9303	0.040*
H44	0.4751	0.0571	0.9193	0.042*
H45	0.4229	−0.0398	0.7456	0.042*
H46	0.2971	−0.0315	0.5773	0.038*
H47A	0.1464	−0.0078	0.6236	0.040*
H47B	0.0874	0.0436	0.4967	0.040*
H48A	0.1571	0.0825	0.8302	0.072*
H48B	0.0683	0.0574	0.7651	0.072*
H48C	0.0972	0.1331	0.7033	0.072*
H1A	0.4644	0.2318	0.2690	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0292 (10)	0.0346 (9)	0.0260 (9)	0.0016 (7)	0.0088 (7)	0.0070 (7)
N2	0.0283 (10)	0.0406 (11)	0.0337 (10)	0.0030 (8)	0.0094 (8)	0.0059 (8)
N5	0.0282 (9)	0.0271 (9)	0.0243 (9)	−0.0011 (7)	0.0081 (7)	0.0018 (7)
N6	0.0272 (10)	0.0490 (11)	0.0280 (9)	−0.0034 (8)	0.0047 (8)	0.0083 (8)
N7	0.0278 (10)	0.0320 (9)	0.0258 (9)	−0.0005 (7)	0.0082 (7)	0.0006 (7)
N4	0.0294 (9)	0.0295 (9)	0.0275 (9)	−0.0010 (7)	0.0084 (7)	0.0051 (7)
C3	0.0327 (12)	0.0348 (12)	0.0283 (11)	0.0043 (9)	0.0095 (9)	0.0076 (9)
C3A	0.0258 (11)	0.0279 (10)	0.0267 (10)	0.0019 (8)	0.0077 (8)	0.0008 (8)
C4	0.0297 (11)	0.0224 (10)	0.0253 (10)	0.0019 (8)	0.0100 (9)	−0.0016 (8)
C6	0.0282 (11)	0.0280 (11)	0.0244 (10)	−0.0009 (8)	0.0079 (9)	−0.0019 (8)
C7A	0.0266 (11)	0.0257 (10)	0.0267 (10)	0.0013 (8)	0.0101 (9)	0.0000 (8)
C41	0.0295 (11)	0.0289 (10)	0.0252 (10)	0.0017 (8)	0.0108 (8)	0.0063 (8)
C42	0.0355 (12)	0.0282 (11)	0.0304 (11)	0.0049 (9)	0.0111 (9)	0.0016 (9)
C43	0.0332 (12)	0.0384 (12)	0.0303 (11)	−0.0002 (9)	0.0096 (10)	−0.0004 (9)
C44	0.0306 (12)	0.0445 (13)	0.0313 (11)	0.0049 (10)	0.0105 (9)	0.0072 (10)
C45	0.0337 (12)	0.0355 (12)	0.0402 (12)	0.0098 (9)	0.0163 (10)	0.0073 (10)
C46	0.0359 (12)	0.0288 (11)	0.0333 (11)	0.0016 (9)	0.0159 (9)	0.0026 (9)
C47	0.0317 (12)	0.0344 (12)	0.0341 (11)	−0.0033 (9)	0.0089 (9)	0.0089 (9)
C48	0.0358 (13)	0.0720 (18)	0.0389 (13)	0.0049 (12)	0.0149 (11)	0.0030 (12)
O1	0.0272 (11)	0.0367 (12)	0.0339 (12)	0.000	0.0091 (9)	0.000

Geometric parameters (Å, º)

N1—C7A	1.346 (3)	C41—C42	1.385 (3)
N1—N2	1.374 (2)	C41—C46	1.387 (3)
N1—H1	0.86	C42—C43	1.382 (3)
N2—C3	1.318 (3)	C42—H2	0.95
N5—C4	1.335 (3)	C43—C44	1.384 (3)
N5—C6	1.359 (2)	C43—H43	0.95
N6—C6	1.337 (2)	C44—C45	1.385 (3)
N6—H6A	0.86	C44—H44	0.95
N6—H6B	0.86	C45—C46	1.384 (3)
N7—C7A	1.344 (3)	C45—H45	0.95
N7—C6	1.347 (3)	C46—H46	0.95
N4—C4	1.357 (2)	C47—C48	1.502 (3)
N4—C41	1.434 (3)	C47—H47A	0.99
N4—C47	1.467 (3)	C47—H47B	0.99
C3—C3A	1.416 (3)	C48—H48A	0.98
C3—H3	0.95	C48—H48B	0.98
C3A—C7A	1.391 (3)	C48—H48C	0.98
C3A—C4	1.429 (3)	O1—H1A	0.82
C7A—N1—N2	111.06 (17)	C46—C41—N4	120.05 (18)
C7A—N1—H1	128.2	C43—C42—C41	120.2 (2)
N2—N1—H1	120.4	C43—C42—H2	119.9
C3—N2—N1	105.88 (17)	C41—C42—H2	119.9
C4—N5—C6	118.95 (17)	C42—C43—C44	119.8 (2)
C6—N6—H6A	118.9	C42—C43—H43	120.1
C6—N6—H6B	123.8	C44—C43—H43	120.1
H6A—N6—H6B	117.2	C43—C44—C45	120.0 (2)
C7A—N7—C6	112.15 (17)	C43—C44—H44	120.0
C4—N4—C41	119.56 (16)	C45—C44—H44	120.0
C4—N4—C47	123.04 (17)	C46—C45—C44	120.4 (2)
C41—N4—C47	117.34 (16)	C46—C45—H45	119.8
N2—C3—C3A	111.19 (18)	C44—C45—H45	119.8
N2—C3—H3	124.4	C45—C46—C41	119.5 (2)
C3A—C3—H3	124.4	C45—C46—H46	120.3
C7A—C3A—C3	104.46 (17)	C41—C46—H46	120.3
C7A—C3A—C4	115.22 (18)	N4—C47—C48	112.15 (18)
C3—C3A—C4	140.32 (19)	N4—C47—H47A	109.2
N5—C4—N4	118.69 (17)	C48—C47—H47A	109.2
N5—C4—C3A	119.39 (17)	N4—C47—H47B	109.2
N4—C4—C3A	121.90 (18)	C48—C47—H47B	109.2
N6—C6—N7	117.28 (18)	H47A—C47—H47B	107.9
N6—C6—N5	115.60 (18)	C47—C48—H48A	109.5
N7—C6—N5	127.11 (18)	C47—C48—H48B	109.5
N7—C7A—N1	125.45 (18)	H48A—C48—H48B	109.5
N7—C7A—C3A	127.15 (18)	C47—C48—H48C	109.5
N1—C7A—C3A	107.41 (17)	H48A—C48—H48C	109.5
C42—C41—C46	120.17 (19)	H48B—C48—H48C	109.5
C42—C41—N4	119.75 (18)
C7A—N1—N2—C3	0.5 (2)	N2—N1—C7A—N7	179.92 (18)
N1—N2—C3—C3A	−0.3 (2)	N2—N1—C7A—C3A	−0.5 (2)
N2—C3—C3A—C7A	0.0 (2)	C3—C3A—C7A—N7	179.85 (19)
N2—C3—C3A—C4	179.1 (2)	C4—C3A—C7A—N7	0.5 (3)
C6—N5—C4—N4	−175.97 (17)	C3—C3A—C7A—N1	0.3 (2)
C6—N5—C4—C3A	2.4 (3)	C4—C3A—C7A—N1	−179.04 (17)
C41—N4—C4—N5	−175.65 (17)	C4—N4—C41—C42	78.2 (2)
C47—N4—C4—N5	1.6 (3)	C47—N4—C41—C42	−99.2 (2)
C41—N4—C4—C3A	6.0 (3)	C4—N4—C41—C46	−99.8 (2)
C47—N4—C4—C3A	−176.79 (19)	C47—N4—C41—C46	82.8 (2)
C7A—C3A—C4—N5	−2.0 (3)	C46—C41—C42—C43	2.4 (3)
C3—C3A—C4—N5	179.0 (2)	N4—C41—C42—C43	−175.62 (18)
C7A—C3A—C4—N4	176.32 (17)	C41—C42—C43—C44	−1.2 (3)
C3—C3A—C4—N4	−2.6 (4)	C42—C43—C44—C45	−0.5 (3)
C7A—N7—C6—N6	−179.54 (17)	C43—C44—C45—C46	1.0 (3)
C7A—N7—C6—N5	−0.1 (3)	C44—C45—C46—C41	0.1 (3)
C4—N5—C6—N6	178.06 (17)	C42—C41—C46—C45	−1.8 (3)
C4—N5—C6—N7	−1.4 (3)	N4—C41—C46—C45	176.16 (18)
C6—N7—C7A—N1	179.99 (18)	C4—N4—C47—C48	−106.3 (2)
C6—N7—C7A—C3A	0.5 (3)	C41—N4—C47—C48	71.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2	0.82	1.91	2.726 (2)	169
N1—H1···N7^i	0.86	2.11	2.971 (2)	179
N6—H6A···N5^ii	0.86	2.44	3.293 (2)	169
N6—H6B···O1^i	0.86	2.04	2.897 (2)	179
C3—H3···Cg1	0.95	2.47	3.260 (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

Crystal data

2(C13H14N6O)·H2O	Z = 2
Mr = 558.62	F(000) = 588
Triclinic, P1	Dx = 1.338 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9516 (5) Å	Cell parameters from 6316 reflections
b = 12.0627 (7) Å	θ = 3.8–27.5°
c = 12.9053 (7) Å	µ = 0.09 mm^−1
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) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	6316 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	4620 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ϕ & ω scans	θmax = 27.5°, θmin = 3.8°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −11→11
Tmin = 0.955, Tmax = 0.963	k = −15→15
31433 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.025P)^2 + 1.067P] where P = (Fo^2 + 2Fc^2)/3
6316 reflections	(Δ/σ)max = 0.001
374 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O14	0.88960 (14)	0.39539 (11)	0.50974 (10)	0.0277 (3)
N11	0.16054 (15)	0.09692 (11)	0.51768 (10)	0.0165 (3)
N12	0.28222 (15)	0.16483 (12)	0.55742 (11)	0.0194 (3)
N14	0.50386 (16)	0.10912 (12)	0.25573 (11)	0.0207 (3)
N15	0.28424 (15)	−0.00678 (12)	0.23784 (11)	0.0175 (3)
N16	0.06661 (16)	−0.11967 (12)	0.21153 (11)	0.0226 (3)
N17	0.09054 (15)	−0.01625 (11)	0.36478 (10)	0.0154 (3)
C13	0.38265 (19)	0.16706 (14)	0.48484 (13)	0.0186 (3)
C13A	0.33003 (18)	0.09931 (13)	0.39713 (12)	0.0159 (3)
C14	0.37451 (18)	0.06679 (13)	0.29634 (12)	0.0156 (3)
C16	0.14874 (18)	−0.04505 (13)	0.27428 (12)	0.0156 (3)
C17A	0.18695 (17)	0.05532 (13)	0.42286 (12)	0.0141 (3)
C141	0.60971 (18)	0.18074 (14)	0.31848 (13)	0.0177 (3)
C142	0.69949 (19)	0.13607 (15)	0.39270 (14)	0.0215 (4)
C143	0.79459 (19)	0.20513 (15)	0.45956 (14)	0.0220 (4)
C144	0.80066 (18)	0.31966 (14)	0.44965 (14)	0.0201 (4)
C145	0.71228 (19)	0.36431 (15)	0.37339 (14)	0.0219 (4)
C146	0.61742 (19)	0.29567 (15)	0.30807 (14)	0.0208 (4)
C147	0.9706 (2)	0.35624 (18)	0.59598 (15)	0.0319 (5)
C148	0.5426 (2)	0.0818 (2)	0.14961 (15)	0.0386 (5)
O24	−0.36346 (14)	0.52229 (11)	0.60950 (10)	0.0264 (3)
N21	0.34896 (15)	0.48485 (12)	0.90715 (11)	0.0182 (3)
N22	0.23389 (16)	0.44450 (12)	0.83850 (11)	0.0215 (3)
C23	0.1348 (2)	0.51917 (15)	0.84109 (13)	0.0208 (4)
N24	0.00986 (16)	0.75434 (12)	0.91269 (11)	0.0191 (3)
N26	0.42071 (17)	0.79306 (13)	1.13795 (12)	0.0250 (3)
N27	0.40754 (15)	0.63965 (11)	1.02714 (10)	0.0168 (3)
C27A	0.31927 (18)	0.58162 (13)	0.95342 (12)	0.0154 (3)
C23A	0.18130 (18)	0.60842 (14)	0.91216 (12)	0.0165 (3)
C24	0.13336 (18)	0.71065 (14)	0.95126 (12)	0.0159 (3)
N25	0.21448 (15)	0.76827 (11)	1.02738 (10)	0.0170 (3)
C26	0.34639 (18)	0.73114 (14)	1.06149 (12)	0.0167 (3)
C241	−0.08765 (18)	0.69347 (14)	0.83610 (13)	0.0180 (3)
C242	−0.18882 (19)	0.60792 (16)	0.86520 (13)	0.0229 (4)
C243	−0.28168 (19)	0.54638 (16)	0.79153 (14)	0.0238 (4)
C244	−0.27389 (18)	0.57398 (15)	0.68797 (13)	0.0200 (4)
C245	−0.17221 (19)	0.66035 (15)	0.65863 (13)	0.0211 (4)
C246	−0.07945 (19)	0.71990 (15)	0.73215 (13)	0.0207 (4)
C247	−0.4570 (2)	0.42474 (16)	0.63362 (17)	0.0315 (4)
C248	−0.0328 (2)	0.86190 (16)	0.95045 (16)	0.0322 (5)
O1	0.25840 (13)	0.21899 (10)	0.77303 (9)	0.0229 (3)
H11	0.0877	0.0761	0.5565	0.020*
H16B	−0.0238	−0.1441	0.2247	0.027*
H16A	0.1049	−0.1412	0.1551	0.027*
H13	0.4780	0.2088	0.4907	0.022*
H142	0.6964	0.0575	0.3982	0.026*
H143	0.8547	0.1741	0.5114	0.026*
H145	0.7174	0.4427	0.3663	0.026*
H146	0.5575	0.3266	0.2561	0.025*
H14A	0.9001	0.3186	0.6429	0.048*
H14B	1.0276	0.4194	0.6331	0.048*
H14C	1.0398	0.3037	0.5715	0.048*
H14D	0.6026	0.0178	0.1497	0.058*
H14E	0.6008	0.1460	0.1211	0.058*
H14F	0.4505	0.0634	0.1069	0.058*
H21	0.4204	0.4447	0.9234	0.022*
H23	0.0438	0.5137	0.8004	0.025*
H26B	0.5106	0.7819	1.1581	0.030*
H26A	0.3851	0.8534	1.1585	0.030*
H242	−0.1952	0.5908	0.9364	0.027*
H243	−0.3495	0.4863	0.8118	0.029*
H245	−0.1666	0.6785	0.5876	0.025*
H246	−0.0101	0.7789	0.7118	0.025*
H24A	−0.5255	0.4433	0.6877	0.047*
H24B	−0.3943	0.3677	0.6585	0.047*
H24C	−0.5154	0.3962	0.5712	0.047*
H24D	0.0578	0.9116	0.9683	0.048*
H24E	−0.0926	0.8512	1.0122	0.048*
H24F	−0.0924	0.8950	0.8962	0.048*
H1B	0.2477	0.2853	0.7827	0.034*
H1A	0.2701	0.2131	0.7104	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O14	0.0229 (7)	0.0232 (7)	0.0356 (8)	−0.0003 (5)	−0.0051 (6)	−0.0048 (6)
N11	0.0137 (6)	0.0190 (7)	0.0162 (7)	−0.0006 (5)	0.0019 (5)	−0.0037 (6)
N12	0.0171 (7)	0.0192 (7)	0.0210 (7)	−0.0004 (6)	−0.0002 (6)	−0.0046 (6)
N14	0.0186 (7)	0.0248 (8)	0.0177 (7)	−0.0041 (6)	0.0048 (6)	−0.0021 (6)
N15	0.0160 (7)	0.0198 (7)	0.0165 (7)	0.0004 (6)	0.0019 (5)	−0.0019 (6)
N16	0.0182 (7)	0.0291 (8)	0.0187 (7)	−0.0054 (6)	0.0039 (6)	−0.0081 (6)
N17	0.0148 (7)	0.0163 (7)	0.0146 (7)	−0.0005 (5)	0.0008 (5)	−0.0012 (5)
C13	0.0169 (8)	0.0185 (8)	0.0201 (8)	0.0005 (7)	0.0021 (7)	−0.0030 (7)
C13A	0.0156 (8)	0.0149 (8)	0.0171 (8)	0.0009 (6)	0.0008 (6)	0.0004 (6)
C14	0.0155 (8)	0.0141 (8)	0.0174 (8)	0.0014 (6)	0.0016 (6)	0.0017 (6)
C16	0.0167 (8)	0.0156 (8)	0.0146 (8)	0.0020 (6)	−0.0001 (6)	0.0009 (6)
C17A	0.0143 (7)	0.0136 (8)	0.0146 (8)	0.0028 (6)	0.0005 (6)	0.0003 (6)
C141	0.0144 (8)	0.0196 (9)	0.0190 (8)	−0.0010 (6)	0.0053 (6)	−0.0006 (7)
C142	0.0195 (8)	0.0178 (9)	0.0274 (9)	0.0017 (7)	0.0037 (7)	0.0028 (7)
C143	0.0166 (8)	0.0229 (9)	0.0267 (9)	0.0034 (7)	−0.0016 (7)	0.0044 (7)
C144	0.0136 (8)	0.0203 (9)	0.0259 (9)	−0.0008 (7)	0.0033 (7)	−0.0032 (7)
C145	0.0208 (9)	0.0154 (8)	0.0299 (10)	0.0020 (7)	0.0025 (7)	0.0030 (7)
C146	0.0182 (8)	0.0229 (9)	0.0219 (9)	0.0036 (7)	0.0026 (7)	0.0046 (7)
C147	0.0280 (10)	0.0379 (12)	0.0290 (10)	0.0023 (9)	−0.0039 (8)	−0.0058 (9)
C148	0.0375 (12)	0.0513 (14)	0.0237 (10)	−0.0165 (10)	0.0161 (9)	−0.0090 (9)
O24	0.0225 (6)	0.0321 (7)	0.0235 (7)	0.0007 (5)	−0.0050 (5)	−0.0056 (6)
N21	0.0164 (7)	0.0190 (7)	0.0194 (7)	0.0042 (6)	−0.0011 (6)	−0.0041 (6)
N22	0.0222 (7)	0.0223 (8)	0.0200 (7)	0.0042 (6)	−0.0012 (6)	−0.0061 (6)
C23	0.0215 (9)	0.0217 (9)	0.0195 (8)	0.0049 (7)	−0.0013 (7)	−0.0031 (7)
N24	0.0219 (7)	0.0175 (7)	0.0184 (7)	0.0066 (6)	−0.0035 (6)	−0.0027 (6)
N26	0.0216 (8)	0.0239 (8)	0.0294 (8)	0.0088 (6)	−0.0088 (6)	−0.0120 (7)
N27	0.0172 (7)	0.0161 (7)	0.0170 (7)	0.0025 (6)	0.0000 (6)	−0.0019 (6)
C27A	0.0175 (8)	0.0142 (8)	0.0151 (8)	0.0026 (6)	0.0043 (6)	0.0012 (6)
C23A	0.0189 (8)	0.0177 (8)	0.0129 (8)	0.0020 (7)	0.0006 (6)	−0.0007 (6)
C24	0.0171 (8)	0.0166 (8)	0.0142 (8)	0.0010 (6)	0.0023 (6)	0.0020 (6)
N25	0.0179 (7)	0.0164 (7)	0.0168 (7)	0.0032 (6)	0.0003 (6)	−0.0016 (6)
C26	0.0183 (8)	0.0159 (8)	0.0160 (8)	0.0016 (6)	0.0016 (6)	−0.0003 (6)
C241	0.0182 (8)	0.0187 (8)	0.0180 (8)	0.0078 (7)	−0.0017 (7)	−0.0014 (7)
C242	0.0219 (9)	0.0310 (10)	0.0165 (8)	0.0042 (8)	0.0030 (7)	0.0043 (7)
C243	0.0192 (9)	0.0270 (10)	0.0251 (9)	−0.0001 (7)	0.0016 (7)	0.0048 (8)
C244	0.0153 (8)	0.0240 (9)	0.0211 (9)	0.0062 (7)	−0.0016 (7)	−0.0036 (7)
C245	0.0233 (9)	0.0259 (9)	0.0150 (8)	0.0060 (7)	0.0011 (7)	0.0031 (7)
C246	0.0215 (9)	0.0207 (9)	0.0203 (9)	0.0033 (7)	0.0008 (7)	0.0032 (7)
C247	0.0257 (10)	0.0267 (10)	0.0408 (12)	−0.0005 (8)	−0.0049 (9)	−0.0070 (9)
C248	0.0386 (11)	0.0268 (10)	0.0323 (11)	0.0182 (9)	−0.0136 (9)	−0.0100 (8)
O1	0.0270 (7)	0.0204 (6)	0.0209 (6)	0.0027 (5)	0.0001 (5)	−0.0055 (5)

Geometric parameters (Å, º)

O14—C144	1.361 (2)	O24—C247	1.429 (2)
O14—C147	1.422 (2)	N21—C27A	1.349 (2)
N11—C17A	1.347 (2)	N21—N22	1.379 (2)
N11—N12	1.3759 (19)	N21—H21	0.86
N11—H11	0.86	N22—C23	1.321 (2)
N12—C13	1.321 (2)	C23—C23A	1.417 (2)
N14—C14	1.351 (2)	C23—H23	0.95
N14—C141	1.434 (2)	N24—C24	1.353 (2)
N14—C148	1.461 (2)	N24—C241	1.434 (2)
N15—C14	1.341 (2)	N24—C248	1.461 (2)
N15—C16	1.362 (2)	N26—C26	1.340 (2)
N16—C16	1.342 (2)	N26—H26B	0.86
N16—H16B	0.86	N26—H26A	0.86
N16—H16A	0.86	N27—C26	1.347 (2)
N17—C16	1.345 (2)	N27—C27A	1.351 (2)
N17—C17A	1.354 (2)	C27A—C23A	1.396 (2)
C13—C13A	1.418 (2)	C23A—C24	1.427 (2)
C13—H13	0.95	C24—N25	1.339 (2)
C13A—C17A	1.396 (2)	N25—C26	1.364 (2)
C13A—C14	1.429 (2)	C241—C242	1.379 (2)
C141—C142	1.381 (2)	C241—C246	1.390 (2)
C141—C146	1.392 (2)	C242—C243	1.392 (3)
C142—C143	1.393 (2)	C242—H242	0.95
C142—H142	0.95	C243—C244	1.389 (2)
C143—C144	1.387 (2)	C243—H243	0.95
C143—H143	0.95	C244—C245	1.389 (2)
C144—C145	1.391 (2)	C245—C246	1.379 (2)
C145—C146	1.377 (3)	C245—H245	0.95
C145—H145	0.95	C246—H246	0.95
C146—H146	0.95	C247—H24A	0.98
C147—H14A	0.98	C247—H24B	0.98
C147—H14B	0.98	C247—H24C	0.98
C147—H14C	0.98	C248—H24D	0.98
C148—H14D	0.98	C248—H24E	0.98
C148—H14E	0.98	C248—H24F	0.98
C148—H14F	0.98	O1—H1B	0.82
O24—C244	1.368 (2)	O1—H1A	0.82
C144—O14—C147	118.13 (15)	C27A—N21—N22	111.26 (13)
C17A—N11—N12	111.18 (13)	C27A—N21—H21	127.2
C17A—N11—H11	127.2	N22—N21—H21	120.7
N12—N11—H11	120.5	C23—N22—N21	105.50 (14)
C13—N12—N11	105.72 (13)	N22—C23—C23A	111.60 (15)
C14—N14—C141	119.81 (14)	N22—C23—H23	124.2
C14—N14—C148	122.08 (15)	C23A—C23—H23	124.2
C141—N14—C148	118.09 (14)	C24—N24—C241	120.58 (14)
C14—N15—C16	118.96 (14)	C24—N24—C248	121.65 (14)
C16—N16—H16B	122.1	C241—N24—C248	117.72 (14)
C16—N16—H16A	118.4	C26—N26—H26B	121.8
H16B—N16—H16A	119.4	C26—N26—H26A	118.5
C16—N17—C17A	111.97 (13)	H26B—N26—H26A	118.5
N12—C13—C13A	111.40 (15)	C26—N27—C27A	112.10 (14)
N12—C13—H13	124.3	N21—C27A—N27	125.44 (15)
C13A—C13—H13	124.3	N21—C27A—C23A	107.34 (14)
C17A—C13A—C13	104.23 (14)	N27—C27A—C23A	127.21 (15)
C17A—C13A—C14	114.94 (14)	C27A—C23A—C23	104.28 (14)
C13—C13A—C14	140.80 (15)	C27A—C23A—C24	114.94 (15)
N15—C14—N14	117.87 (14)	C23—C23A—C24	140.78 (16)
N15—C14—C13A	119.52 (14)	N25—C24—N24	117.73 (15)
N14—C14—C13A	122.59 (15)	N25—C24—C23A	119.62 (15)
N16—C16—N17	117.79 (15)	N24—C24—C23A	122.63 (15)
N16—C16—N15	115.03 (14)	C24—N25—C26	118.95 (14)
N17—C16—N15	127.18 (15)	N26—C26—N27	117.62 (15)
N11—C17A—N17	125.30 (14)	N26—C26—N25	115.37 (15)
N11—C17A—C13A	107.44 (14)	N27—C26—N25	127.01 (15)
N17—C17A—C13A	127.26 (15)	C242—C241—C246	119.81 (16)
C142—C141—C146	119.85 (16)	C242—C241—N24	120.10 (15)
C142—C141—N14	119.93 (16)	C246—C241—N24	120.09 (16)
C146—C141—N14	120.16 (15)	C241—C242—C243	120.78 (16)
C141—C142—C143	120.59 (16)	C241—C242—H242	119.6
C141—C142—H142	119.7	C243—C242—H242	119.6
C143—C142—H142	119.7	C244—C243—C242	119.07 (17)
C144—C143—C142	119.33 (16)	C244—C243—H243	120.5
C144—C143—H143	120.3	C242—C243—H243	120.5
C142—C143—H143	120.3	O24—C244—C243	124.21 (16)
O14—C144—C143	124.75 (16)	O24—C244—C245	115.63 (15)
O14—C144—C145	115.33 (16)	C243—C244—C245	120.15 (16)
C143—C144—C145	119.92 (16)	C246—C245—C244	120.27 (16)
C146—C145—C144	120.51 (16)	C246—C245—H245	119.9
C146—C145—H145	119.7	C244—C245—H245	119.9
C144—C145—H145	119.7	C245—C246—C241	119.90 (16)
C145—C146—C141	119.78 (16)	C245—C246—H246	120.1
C145—C146—H146	120.1	C241—C246—H246	120.1
C141—C146—H146	120.1	O24—C247—H24A	109.5
O14—C147—H14A	109.5	O24—C247—H24B	109.5
O14—C147—H14B	109.5	H24A—C247—H24B	109.5
H14A—C147—H14B	109.5	O24—C247—H24C	109.5
O14—C147—H14C	109.5	H24A—C247—H24C	109.5
H14A—C147—H14C	109.5	H24B—C247—H24C	109.5
H14B—C147—H14C	109.5	N24—C248—H24D	109.5
N14—C148—H14D	109.5	N24—C248—H24E	109.5
N14—C148—H14E	109.5	H24D—C248—H24E	109.5
H14D—C148—H14E	109.5	N24—C248—H24F	109.5
N14—C148—H14F	109.5	H24D—C248—H24F	109.5
H14D—C148—H14F	109.5	H24E—C248—H24F	109.5
H14E—C148—H14F	109.5	H1B—O1—H1A	103.8
C244—O24—C247	117.61 (15)
C17A—N11—N12—C13	1.62 (18)	C27A—N21—N22—C23	1.61 (19)
N11—N12—C13—C13A	−1.04 (19)	N21—N22—C23—C23A	−0.96 (19)
N12—C13—C13A—C17A	0.14 (19)	N22—N21—C27A—N27	177.49 (15)
N12—C13—C13A—C14	178.2 (2)	N22—N21—C27A—C23A	−1.62 (18)
C16—N15—C14—N14	−175.71 (15)	C26—N27—C27A—N21	−177.82 (16)
C16—N15—C14—C13A	2.9 (2)	C26—N27—C27A—C23A	1.1 (2)
C141—N14—C14—N15	−174.76 (15)	N21—C27A—C23A—C23	0.96 (18)
C148—N14—C14—N15	3.4 (3)	N27—C27A—C23A—C23	−178.13 (16)
C141—N14—C14—C13A	6.6 (2)	N21—C27A—C23A—C24	−178.77 (14)
C148—N14—C14—C13A	−175.14 (18)	N27—C27A—C23A—C24	2.1 (2)
C17A—C13A—C14—N15	−4.3 (2)	N22—C23—C23A—C27A	0.0 (2)
C13—C13A—C14—N15	177.8 (2)	N22—C23—C23A—C24	179.6 (2)
C17A—C13A—C14—N14	174.26 (15)	C241—N24—C24—N25	−175.73 (15)
C13—C13A—C14—N14	−3.7 (3)	C248—N24—C24—N25	1.4 (2)
C17A—N17—C16—N16	177.10 (15)	C241—N24—C24—C23A	6.0 (2)
C17A—N17—C16—N15	−2.8 (2)	C248—N24—C24—C23A	−176.88 (17)
C14—N15—C16—N16	−179.02 (15)	C27A—C23A—C24—N25	−4.7 (2)
C14—N15—C16—N17	0.9 (3)	C23—C23A—C24—N25	175.7 (2)
N12—N11—C17A—N17	178.29 (15)	C27A—C23A—C24—N24	173.57 (15)
N12—N11—C17A—C13A	−1.56 (18)	C23—C23A—C24—N24	−6.0 (3)
C16—N17—C17A—N11	−178.81 (15)	N24—C24—N25—C26	−174.38 (14)
C16—N17—C17A—C13A	1.0 (2)	C23A—C24—N25—C26	4.0 (2)
C13—C13A—C17A—N11	0.85 (18)	C27A—N27—C26—N26	177.27 (15)
C14—C13A—C17A—N11	−177.78 (14)	C27A—N27—C26—N25	−2.2 (2)
C13—C13A—C17A—N17	−178.99 (16)	C24—N25—C26—N26	−179.80 (15)
C14—C13A—C17A—N17	2.4 (2)	C24—N25—C26—N27	−0.4 (3)
C14—N14—C141—C142	76.1 (2)	C24—N24—C241—C242	78.1 (2)
C148—N14—C141—C142	−102.1 (2)	C248—N24—C241—C242	−99.2 (2)
C14—N14—C141—C146	−100.91 (19)	C24—N24—C241—C246	−101.36 (19)
C148—N14—C141—C146	80.8 (2)	C248—N24—C241—C246	81.4 (2)
C146—C141—C142—C143	2.0 (3)	C246—C241—C242—C243	0.9 (3)
N14—C141—C142—C143	−175.07 (15)	N24—C241—C242—C243	−178.48 (16)
C141—C142—C143—C144	−1.3 (3)	C241—C242—C243—C244	−1.6 (3)
C147—O14—C144—C143	−7.0 (2)	C247—O24—C244—C243	−8.5 (2)
C147—O14—C144—C145	173.43 (16)	C247—O24—C244—C245	172.70 (15)
C142—C143—C144—O14	−179.56 (16)	C242—C243—C244—O24	−177.39 (16)
C142—C143—C144—C145	0.0 (3)	C242—C243—C244—C245	1.4 (3)
O14—C144—C145—C146	−179.81 (16)	O24—C244—C245—C246	178.26 (15)
C143—C144—C145—C146	0.6 (3)	C243—C244—C245—C246	−0.6 (3)
C144—C145—C146—C141	0.1 (3)	C244—C245—C246—C241	0.0 (3)
C142—C141—C146—C145	−1.4 (2)	C242—C241—C246—C245	−0.1 (3)
N14—C141—C146—C145	175.66 (15)	N24—C241—C246—C245	179.27 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N12	0.82	2.05	2.860 (2)	168
O1—H1B···N22	0.82	2.05	2.856 (2)	168
N11—H11···N17^i	0.86	2.01	2.868 (2)	174
N21—H21···N27^ii	0.86	2.02	2.875 (2)	175
N16—H16A···N25^iii	0.86	2.25	3.099 (2)	167
N26—H26A···N15^iv	0.86	2.23	3.076 (2)	170
N16—H16B···O1^i	0.86	2.21	3.059 (2)	169
N26—H26B···O1^ii	0.86	2.22	3.073 (2)	170
C13—H13···Cg2	0.95	2.52	3.300 (2)	139
C23—H23···Cg3	0.95	2.62	3.393 (2)	139

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y+1, −z+2; (iii) x, y−1, z−1; (iv) x, y+1, z+1.

(VIII) N⁴-Benzyl-N⁴-phenylyl-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine monohydrate

Crystal data

C18H16N6·H2O	F(000) = 1408
Mr = 334.38	Dx = 1.362 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7493 reflections
a = 10.1880 (11) Å	θ = 3.0–27.5°
b = 9.5136 (10) Å	µ = 0.09 mm^−1
c = 33.695 (4) Å	T = 120 K
β = 93.131 (7)°	Block, colourless
V = 3261.0 (6) Å^3	0.44 × 0.33 × 0.24 mm
Z = 8

Data collection

Bruker-Nonius KappaCCD diffractometer	7493 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3887 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.095
ϕ & ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −13→13
Tmin = 0.968, Tmax = 0.979	k = −12→12
83278 measured reflections	l = −43→43

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.220	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1085P)^2 + 1.9398P] where P = (Fo^2 + 2Fc^2)/3
7493 reflections	(Δ/σ)max < 0.001
451 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.4954 (2)	0.3661 (3)	0.66767 (7)	0.0281 (6)
N12	0.4359 (2)	0.3813 (3)	0.70291 (7)	0.0294 (6)
N14	0.8322 (2)	0.4853 (3)	0.75854 (7)	0.0263 (5)
N15	0.8722 (2)	0.4543 (2)	0.69310 (7)	0.0260 (5)
N16	0.9199 (2)	0.4348 (3)	0.62837 (7)	0.0323 (6)
N17	0.7076 (2)	0.3894 (2)	0.64284 (7)	0.0264 (5)
C13	0.5304 (3)	0.4151 (3)	0.72940 (8)	0.0285 (7)
C13A	0.6531 (3)	0.4201 (3)	0.71188 (8)	0.0261 (6)
C14	0.7865 (3)	0.4533 (3)	0.72154 (8)	0.0245 (6)
C16	0.8296 (3)	0.4254 (3)	0.65569 (8)	0.0269 (6)
C17A	0.6242 (3)	0.3907 (3)	0.67209 (8)	0.0248 (6)
C141	0.7546 (3)	0.4620 (3)	0.79197 (8)	0.0268 (6)
C142	0.7339 (3)	0.3267 (3)	0.80463 (9)	0.0317 (7)
C143	0.6594 (3)	0.3043 (4)	0.83683 (9)	0.0350 (7)
C144	0.6076 (3)	0.4164 (4)	0.85628 (9)	0.0372 (8)
C145	0.6299 (3)	0.5500 (4)	0.84353 (10)	0.0409 (8)
C146	0.7025 (3)	0.5728 (3)	0.81116 (9)	0.0337 (7)
C147	0.9603 (3)	0.5512 (3)	0.76613 (9)	0.0285 (7)
C151	1.0688 (3)	0.4536 (3)	0.78000 (8)	0.0293 (7)
C152	1.0724 (3)	0.3144 (3)	0.76936 (9)	0.0339 (7)
C153	1.1775 (3)	0.2314 (4)	0.78229 (10)	0.0395 (8)
C154	1.2785 (3)	0.2859 (4)	0.80574 (11)	0.0462 (9)
C155	1.2751 (3)	0.4247 (4)	0.81655 (11)	0.0492 (9)
C156	1.1709 (3)	0.5083 (4)	0.80370 (10)	0.0386 (8)
O1	0.1674 (2)	0.3991 (3)	0.67914 (6)	0.0438 (6)
N21	0.5882 (2)	0.3153 (3)	0.56803 (7)	0.0304 (6)
N22	0.6494 (2)	0.3007 (3)	0.53336 (7)	0.0358 (6)
N24	0.2621 (2)	0.1649 (3)	0.47681 (7)	0.0287 (6)
N25	0.2161 (2)	0.2095 (3)	0.54118 (7)	0.0282 (6)
N26	0.1620 (2)	0.2353 (3)	0.60504 (7)	0.0325 (6)
N27	0.3745 (2)	0.2858 (3)	0.59207 (7)	0.0279 (6)
C23	0.5578 (3)	0.2608 (3)	0.50660 (9)	0.0336 (7)
C23A	0.4347 (3)	0.2506 (3)	0.52338 (8)	0.0282 (7)
C24	0.3035 (3)	0.2088 (3)	0.51343 (8)	0.0280 (7)
C26	0.2548 (3)	0.2452 (3)	0.57856 (8)	0.0275 (7)
C27A	0.4597 (3)	0.2850 (3)	0.56293 (8)	0.0270 (6)
C241	0.3425 (3)	0.1765 (3)	0.44351 (8)	0.0295 (7)
C242	0.3712 (3)	0.3066 (3)	0.42853 (9)	0.0322 (7)
C243	0.4477 (3)	0.3159 (4)	0.39610 (9)	0.0359 (8)
C244	0.4918 (3)	0.1968 (4)	0.37829 (9)	0.0387 (8)
C245	0.4616 (3)	0.0669 (4)	0.39340 (9)	0.0384 (8)
C246	0.3870 (3)	0.0571 (3)	0.42601 (9)	0.0340 (7)
C247	0.1347 (3)	0.0982 (3)	0.47029 (9)	0.0327 (7)
C251	0.0235 (3)	0.1936 (3)	0.45735 (8)	0.0292 (7)
C252	0.0296 (3)	0.3375 (3)	0.46150 (9)	0.0346 (7)
C253	−0.0782 (3)	0.4204 (4)	0.44958 (9)	0.0405 (8)
C254	−0.1897 (3)	0.3589 (4)	0.43346 (10)	0.0446 (9)
C255	−0.1956 (3)	0.2159 (4)	0.42920 (10)	0.0446 (9)
C256	−0.0905 (3)	0.1341 (4)	0.44097 (9)	0.0341 (7)
O2	0.9139 (2)	0.2560 (2)	0.55334 (6)	0.0386 (6)
H11	0.4476	0.3346	0.6432	0.034*
H16A	0.9059	0.4011	0.6010	0.039*
H16B	1.0082	0.4568	0.6397	0.039*
H13	0.5178	0.4336	0.7566	0.034*
H142	0.7708	0.2494	0.7913	0.038*
H143	0.6436	0.2113	0.8456	0.042*
H144	0.5564	0.4011	0.8786	0.045*
H145	0.5947	0.6276	0.8572	0.049*
H146	0.7165	0.6659	0.8021	0.040*
H14A	0.9518	0.6253	0.7864	0.034*
H14B	0.9857	0.5976	0.7414	0.034*
H152	1.0026	0.2751	0.7531	0.041*
H153	1.1795	0.1352	0.7748	0.047*
H154	1.3505	0.2281	0.8145	0.055*
H155	1.3449	0.4634	0.8329	0.059*
H156	1.1694	0.6045	0.8113	0.046*
H1A	0.2505	0.3906	0.6950	0.066*
H1B	0.1062	0.3923	0.7005	0.066*
H21	0.6367	0.3441	0.5926	0.037*
H26A	0.1768	0.2735	0.6319	0.039*
H26B	0.0726	0.2215	0.5935	0.039*
H23	0.5729	0.2414	0.4796	0.040*
H242	0.3387	0.3893	0.4404	0.039*
H243	0.4700	0.4056	0.3861	0.043*
H244	0.5429	0.2037	0.3556	0.046*
H245	0.4924	−0.0160	0.3812	0.046*
H246	0.3663	−0.0325	0.4364	0.041*
H24A	0.1123	0.0513	0.4953	0.039*
H24B	0.1422	0.0242	0.4499	0.039*
H252	0.1075	0.3804	0.4725	0.042*
H253	−0.0740	0.5195	0.4527	0.049*
H254	−0.2632	0.4152	0.4252	0.053*
H255	−0.2734	0.1732	0.4180	0.054*
H256	−0.0959	0.0350	0.4378	0.041*
H2A	0.8281	0.2789	0.5404	0.058*
H2B	0.9704	0.2539	0.5307	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0230 (13)	0.0404 (15)	0.0208 (12)	0.0016 (11)	0.0006 (10)	−0.0009 (11)
N12	0.0252 (13)	0.0365 (14)	0.0264 (13)	0.0026 (11)	0.0011 (10)	0.0009 (11)
N14	0.0231 (12)	0.0340 (14)	0.0216 (12)	−0.0037 (10)	−0.0018 (10)	−0.0018 (10)
N15	0.0243 (12)	0.0297 (13)	0.0241 (12)	−0.0035 (10)	0.0007 (10)	−0.0011 (10)
N16	0.0267 (13)	0.0457 (16)	0.0244 (13)	−0.0010 (11)	0.0005 (10)	−0.0045 (11)
N17	0.0231 (13)	0.0320 (14)	0.0238 (12)	0.0020 (10)	−0.0001 (10)	−0.0001 (10)
C13	0.0281 (16)	0.0321 (17)	0.0250 (15)	0.0027 (13)	−0.0007 (12)	0.0000 (12)
C13A	0.0279 (16)	0.0261 (15)	0.0242 (15)	0.0012 (12)	−0.0008 (12)	0.0010 (12)
C14	0.0233 (15)	0.0246 (15)	0.0255 (15)	0.0004 (12)	−0.0002 (12)	0.0003 (12)
C16	0.0256 (15)	0.0278 (16)	0.0272 (15)	0.0025 (12)	0.0011 (12)	−0.0009 (12)
C17A	0.0222 (15)	0.0278 (15)	0.0240 (14)	0.0010 (12)	−0.0017 (11)	−0.0003 (12)
C141	0.0219 (14)	0.0359 (17)	0.0221 (14)	−0.0011 (13)	−0.0026 (11)	−0.0016 (12)
C142	0.0330 (17)	0.0300 (17)	0.0317 (17)	0.0009 (13)	−0.0015 (13)	0.0021 (13)
C143	0.0318 (17)	0.0413 (19)	0.0317 (17)	−0.0044 (14)	0.0008 (13)	0.0091 (14)
C144	0.0308 (17)	0.055 (2)	0.0255 (16)	−0.0074 (15)	−0.0018 (13)	0.0025 (15)
C145	0.0402 (19)	0.045 (2)	0.0384 (19)	−0.0028 (16)	0.0088 (15)	−0.0123 (16)
C146	0.0321 (17)	0.0335 (18)	0.0357 (17)	−0.0018 (13)	0.0038 (14)	−0.0050 (14)
C147	0.0270 (16)	0.0317 (16)	0.0265 (15)	−0.0048 (13)	−0.0013 (12)	−0.0024 (12)
C151	0.0252 (15)	0.0384 (18)	0.0245 (15)	−0.0023 (13)	0.0027 (12)	0.0012 (13)
C152	0.0320 (17)	0.0369 (18)	0.0327 (17)	−0.0023 (14)	0.0009 (13)	−0.0012 (14)
C153	0.0361 (18)	0.0370 (19)	0.0457 (19)	0.0035 (15)	0.0041 (15)	0.0013 (15)
C154	0.0290 (18)	0.052 (2)	0.057 (2)	0.0054 (16)	−0.0034 (16)	0.0027 (18)
C155	0.0306 (18)	0.053 (2)	0.062 (2)	−0.0021 (16)	−0.0142 (17)	−0.0024 (18)
C156	0.0295 (17)	0.0391 (19)	0.0466 (19)	−0.0018 (14)	−0.0045 (14)	−0.0051 (15)
O1	0.0277 (12)	0.0718 (17)	0.0319 (12)	−0.0007 (11)	0.0014 (9)	−0.0089 (11)
N21	0.0248 (13)	0.0456 (16)	0.0207 (12)	−0.0028 (11)	0.0003 (10)	−0.0023 (11)
N22	0.0295 (14)	0.0528 (17)	0.0250 (13)	−0.0029 (12)	0.0018 (11)	−0.0024 (12)
N24	0.0263 (13)	0.0365 (15)	0.0230 (13)	−0.0027 (11)	−0.0003 (10)	−0.0025 (10)
N25	0.0259 (13)	0.0350 (14)	0.0235 (12)	0.0001 (11)	−0.0004 (10)	−0.0013 (10)
N26	0.0235 (13)	0.0510 (17)	0.0232 (13)	−0.0005 (11)	0.0031 (10)	−0.0038 (11)
N27	0.0220 (13)	0.0381 (15)	0.0235 (12)	0.0021 (11)	0.0004 (10)	−0.0015 (11)
C23	0.0300 (16)	0.049 (2)	0.0215 (15)	−0.0010 (14)	0.0007 (13)	−0.0014 (14)
C23A	0.0246 (15)	0.0375 (17)	0.0222 (14)	−0.0004 (13)	−0.0010 (12)	−0.0006 (12)
C24	0.0283 (16)	0.0314 (16)	0.0241 (15)	0.0003 (12)	0.0001 (12)	−0.0004 (12)
C26	0.0269 (16)	0.0296 (16)	0.0255 (15)	0.0022 (12)	−0.0021 (12)	0.0005 (12)
C27A	0.0257 (15)	0.0302 (16)	0.0248 (15)	0.0001 (12)	−0.0016 (12)	−0.0004 (12)
C241	0.0264 (16)	0.0403 (18)	0.0214 (15)	−0.0006 (13)	−0.0036 (12)	−0.0030 (13)
C242	0.0317 (17)	0.0362 (18)	0.0283 (16)	0.0030 (14)	−0.0033 (13)	0.0028 (13)
C243	0.0313 (17)	0.045 (2)	0.0313 (17)	0.0053 (15)	−0.0013 (14)	0.0099 (14)
C244	0.0315 (17)	0.058 (2)	0.0263 (16)	0.0032 (16)	0.0002 (13)	0.0009 (15)
C245	0.0317 (17)	0.046 (2)	0.0376 (18)	0.0062 (15)	−0.0006 (14)	−0.0079 (15)
C246	0.0313 (17)	0.0365 (18)	0.0339 (17)	0.0031 (14)	−0.0008 (14)	−0.0030 (14)
C247	0.0309 (17)	0.0379 (18)	0.0290 (16)	−0.0084 (14)	−0.0028 (13)	−0.0014 (13)
C251	0.0246 (15)	0.0419 (19)	0.0212 (14)	−0.0031 (13)	0.0009 (12)	0.0012 (13)
C252	0.0328 (17)	0.0431 (19)	0.0279 (16)	−0.0066 (14)	0.0015 (13)	−0.0011 (14)
C253	0.0386 (19)	0.044 (2)	0.0392 (19)	0.0017 (15)	0.0021 (15)	0.0087 (15)
C254	0.0299 (18)	0.058 (2)	0.046 (2)	0.0074 (16)	−0.0011 (15)	0.0038 (17)
C255	0.0276 (18)	0.063 (3)	0.043 (2)	−0.0032 (16)	0.0000 (15)	−0.0009 (17)
C256	0.0284 (17)	0.0445 (19)	0.0294 (16)	−0.0075 (14)	0.0003 (13)	−0.0023 (14)
O2	0.0288 (12)	0.0552 (15)	0.0319 (12)	−0.0015 (10)	0.0026 (9)	−0.0043 (10)

Geometric parameters (Å, º)

N11—C17A	1.333 (3)	N21—C27A	1.342 (4)
N11—N12	1.370 (3)	N21—N22	1.361 (3)
N11—H11	0.98	N21—H21	0.9799
N12—C13	1.317 (4)	N22—C23	1.318 (4)
N14—C14	1.342 (3)	N24—C24	1.348 (3)
N14—C141	1.428 (3)	N24—C241	1.429 (4)
N14—C147	1.457 (3)	N24—C247	1.450 (4)
N15—C14	1.331 (3)	N25—C24	1.325 (4)
N15—C16	1.339 (4)	N25—C26	1.342 (3)
N16—C16	1.340 (4)	N26—C26	1.338 (4)
N16—H16A	0.98	N26—H26A	0.9799
N16—H16B	0.9799	N26—H26B	0.98
N17—C17A	1.336 (3)	N27—C26	1.335 (4)
N17—C16	1.338 (4)	N27—C27A	1.346 (4)
C13—C13A	1.412 (4)	C23—C23A	1.407 (4)
C13—H13	0.95	C23—H23	0.95
C13A—C17A	1.385 (4)	C23A—C27A	1.382 (4)
C13A—C14	1.416 (4)	C23A—C24	1.417 (4)
C141—C146	1.360 (4)	C241—C246	1.369 (4)
C141—C142	1.377 (4)	C241—C242	1.374 (4)
C142—C143	1.375 (4)	C242—C243	1.379 (4)
C142—H142	0.95	C242—H242	0.95
C143—C144	1.372 (5)	C243—C244	1.369 (4)
C143—H143	0.95	C243—H243	0.95
C144—C145	1.365 (5)	C244—C245	1.377 (5)
C144—H144	0.95	C244—H244	0.95
C145—C146	1.369 (4)	C245—C246	1.373 (4)
C145—H145	0.95	C245—H245	0.95
C146—H146	0.95	C246—H246	0.95
C147—C151	1.498 (4)	C247—C251	1.498 (4)
C147—H14A	0.99	C247—H24A	0.99
C147—H14B	0.99	C247—H24B	0.99
C151—C152	1.373 (4)	C251—C252	1.377 (4)
C151—C156	1.378 (4)	C251—C256	1.380 (4)
C152—C153	1.382 (4)	C252—C253	1.393 (4)
C152—H152	0.95	C252—H252	0.95
C153—C154	1.365 (5)	C253—C254	1.364 (5)
C153—H153	0.95	C253—H253	0.95
C154—C155	1.371 (5)	C254—C255	1.369 (5)
C154—H154	0.95	C254—H254	0.95
C155—C156	1.377 (5)	C255—C256	1.365 (5)
C155—H155	0.95	C255—H255	0.95
C156—H156	0.95	C256—H256	0.95
O1—H1A	0.9799	O2—H2A	0.98
O1—H1B	0.98	O2—H2B	0.9799
C17A—N11—N12	111.4 (2)	C27A—N21—N22	111.0 (2)
C17A—N11—H11	126.1	C27A—N21—H21	127.7
N12—N11—H11	122.5	N22—N21—H21	121.3
C13—N12—N11	105.7 (2)	C23—N22—N21	106.0 (2)
C14—N14—C141	121.2 (2)	C24—N24—C241	122.0 (2)
C14—N14—C147	121.5 (2)	C24—N24—C247	120.5 (2)
C141—N14—C147	117.2 (2)	C241—N24—C247	117.5 (2)
C14—N15—C16	119.0 (2)	C24—N25—C26	119.3 (2)
C16—N16—H16A	123.7	C26—N26—H26A	120.8
C16—N16—H16B	113.4	C26—N26—H26B	114.8
H16A—N16—H16B	121.3	H26A—N26—H26B	120.7
C17A—N17—C16	112.1 (2)	C26—N27—C27A	111.3 (2)
N12—C13—C13A	110.9 (3)	N22—C23—C23A	111.0 (3)
N12—C13—H13	124.6	N22—C23—H23	124.5
C13A—C13—H13	124.6	C23A—C23—H23	124.5
C17A—C13A—C13	104.6 (2)	C27A—C23A—C23	104.4 (3)
C17A—C13A—C14	114.7 (3)	C27A—C23A—C24	114.6 (3)
C13—C13A—C14	140.5 (3)	C23—C23A—C24	140.8 (3)
N15—C14—N14	117.3 (2)	N25—C24—N24	117.3 (3)
N15—C14—C13A	119.7 (2)	N25—C24—C23A	119.5 (3)
N14—C14—C13A	123.0 (3)	N24—C24—C23A	123.2 (3)
N17—C16—N15	127.2 (3)	N27—C26—N26	117.3 (2)
N17—C16—N16	117.1 (2)	N27—C26—N25	127.5 (3)
N15—C16—N16	115.7 (3)	N26—C26—N25	115.2 (3)
N11—C17A—N17	125.3 (2)	N21—C27A—N27	124.7 (2)
N11—C17A—C13A	107.4 (2)	N21—C27A—C23A	107.5 (3)
N17—C17A—C13A	127.3 (3)	N27—C27A—C23A	127.8 (3)
C146—C141—C142	120.5 (3)	C246—C241—C242	120.5 (3)
C146—C141—N14	120.2 (3)	C246—C241—N24	119.4 (3)
C142—C141—N14	119.4 (3)	C242—C241—N24	120.1 (3)
C143—C142—C141	119.3 (3)	C241—C242—C243	119.3 (3)
C143—C142—H142	120.3	C241—C242—H242	120.3
C141—C142—H142	120.3	C243—C242—H242	120.3
C144—C143—C142	120.0 (3)	C244—C243—C242	120.5 (3)
C144—C143—H143	120.0	C244—C243—H243	119.8
C142—C143—H143	120.0	C242—C243—H243	119.8
C145—C144—C143	119.9 (3)	C243—C244—C245	119.7 (3)
C145—C144—H144	120.0	C243—C244—H244	120.2
C143—C144—H144	120.0	C245—C244—H244	120.2
C144—C145—C146	120.3 (3)	C246—C245—C244	120.1 (3)
C144—C145—H145	119.8	C246—C245—H245	120.0
C146—C145—H145	119.8	C244—C245—H245	120.0
C141—C146—C145	119.9 (3)	C241—C246—C245	120.0 (3)
C141—C146—H146	120.1	C241—C246—H246	120.0
C145—C146—H146	120.1	C245—C246—H246	120.0
N14—C147—C151	115.3 (2)	N24—C247—C251	115.8 (3)
N14—C147—H14A	108.5	N24—C247—H24A	108.3
C151—C147—H14A	108.5	C251—C247—H24A	108.3
N14—C147—H14B	108.5	N24—C247—H24B	108.3
C151—C147—H14B	108.5	C251—C247—H24B	108.3
H14A—C147—H14B	107.5	H24A—C247—H24B	107.4
C152—C151—C156	119.0 (3)	C252—C251—C256	118.7 (3)
C152—C151—C147	123.1 (3)	C252—C251—C247	123.0 (3)
C156—C151—C147	117.9 (3)	C256—C251—C247	118.3 (3)
C151—C152—C153	120.0 (3)	C251—C252—C253	120.2 (3)
C151—C152—H152	120.0	C251—C252—H252	119.9
C153—C152—H152	120.0	C253—C252—H252	119.9
C154—C153—C152	120.8 (3)	C254—C253—C252	119.9 (3)
C154—C153—H153	119.6	C254—C253—H253	120.0
C152—C153—H153	119.6	C252—C253—H253	120.0
C153—C154—C155	119.4 (3)	C253—C254—C255	119.9 (3)
C153—C154—H154	120.3	C253—C254—H254	120.1
C155—C154—H154	120.3	C255—C254—H254	120.1
C154—C155—C156	120.2 (3)	C256—C255—C254	120.4 (3)
C154—C155—H155	119.9	C256—C255—H255	119.8
C156—C155—H155	119.9	C254—C255—H255	119.8
C155—C156—C151	120.6 (3)	C255—C256—C251	120.8 (3)
C155—C156—H156	119.7	C255—C256—H256	119.6
C151—C156—H156	119.7	C251—C256—H256	119.6
H1A—O1—H1B	99.2	H2A—O2—H2B	101.9
C17A—N11—N12—C13	−0.4 (3)	C27A—N21—N22—C23	−0.1 (3)
N11—N12—C13—C13A	−0.9 (3)	N21—N22—C23—C23A	0.8 (4)
N12—C13—C13A—C17A	1.8 (3)	N22—C23—C23A—C27A	−1.2 (4)
N12—C13—C13A—C14	176.3 (3)	N22—C23—C23A—C24	−175.3 (4)
C16—N15—C14—N14	−178.8 (2)	C26—N25—C24—N24	176.4 (3)
C16—N15—C14—C13A	0.8 (4)	C26—N25—C24—C23A	−2.3 (4)
C141—N14—C14—N15	−168.3 (2)	C241—N24—C24—N25	171.8 (3)
C147—N14—C14—N15	14.7 (4)	C247—N24—C24—N25	−10.7 (4)
C141—N14—C14—C13A	12.1 (4)	C241—N24—C24—C23A	−9.5 (4)
C147—N14—C14—C13A	−165.0 (3)	C247—N24—C24—C23A	168.0 (3)
C17A—C13A—C14—N15	0.0 (4)	C27A—C23A—C24—N25	2.0 (4)
C13—C13A—C14—N15	−174.1 (3)	C23—C23A—C24—N25	175.7 (4)
C17A—C13A—C14—N14	179.6 (3)	C27A—C23A—C24—N24	−176.7 (3)
C13—C13A—C14—N14	5.5 (6)	C23—C23A—C24—N24	−2.9 (6)
C17A—N17—C16—N15	3.0 (4)	C27A—N27—C26—N26	177.1 (3)
C17A—N17—C16—N16	−176.5 (3)	C27A—N27—C26—N25	−1.4 (4)
C14—N15—C16—N17	−2.6 (4)	C24—N25—C26—N27	2.1 (5)
C14—N15—C16—N16	176.9 (2)	C24—N25—C26—N26	−176.3 (3)
N12—N11—C17A—N17	−177.3 (3)	N22—N21—C27A—N27	177.8 (3)
N12—N11—C17A—C13A	1.5 (3)	N22—N21—C27A—C23A	−0.6 (3)
C16—N17—C17A—N11	176.6 (3)	C26—N27—C27A—N21	−177.1 (3)
C16—N17—C17A—C13A	−2.0 (4)	C26—N27—C27A—C23A	1.0 (4)
C13—C13A—C17A—N11	−2.0 (3)	C23—C23A—C27A—N21	1.1 (3)
C14—C13A—C17A—N11	−178.1 (2)	C24—C23A—C27A—N21	177.0 (3)
C13—C13A—C17A—N17	176.8 (3)	C23—C23A—C27A—N27	−177.3 (3)
C14—C13A—C17A—N17	0.7 (4)	C24—C23A—C27A—N27	−1.4 (5)
C14—N14—C141—C146	−108.3 (3)	C24—N24—C241—C246	113.7 (3)
C147—N14—C141—C146	68.9 (3)	C247—N24—C241—C246	−63.9 (4)
C14—N14—C141—C142	72.1 (4)	C24—N24—C241—C242	−68.3 (4)
C147—N14—C141—C142	−110.7 (3)	C247—N24—C241—C242	114.1 (3)
C146—C141—C142—C143	0.3 (4)	C246—C241—C242—C243	−1.3 (4)
N14—C141—C142—C143	179.9 (2)	N24—C241—C242—C243	−179.3 (3)
C141—C142—C143—C144	−0.7 (4)	C241—C242—C243—C244	1.8 (4)
C142—C143—C144—C145	0.3 (5)	C242—C243—C244—C245	−1.3 (5)
C143—C144—C145—C146	0.6 (5)	C243—C244—C245—C246	0.4 (5)
C142—C141—C146—C145	0.6 (4)	C242—C241—C246—C245	0.4 (4)
N14—C141—C146—C145	−179.0 (3)	N24—C241—C246—C245	178.4 (3)
C144—C145—C146—C141	−1.1 (5)	C244—C245—C246—C241	0.1 (5)
C14—N14—C147—C151	−100.4 (3)	C24—N24—C247—C251	93.8 (3)
C141—N14—C147—C151	82.4 (3)	C241—N24—C247—C251	−88.6 (3)
N14—C147—C151—C152	29.9 (4)	N24—C247—C251—C252	−17.2 (4)
N14—C147—C151—C156	−151.8 (3)	N24—C247—C251—C256	163.6 (3)
C156—C151—C152—C153	−0.2 (5)	C256—C251—C252—C253	0.5 (4)
C147—C151—C152—C153	178.1 (3)	C247—C251—C252—C253	−178.7 (3)
C151—C152—C153—C154	0.2 (5)	C251—C252—C253—C254	−0.5 (5)
C152—C153—C154—C155	0.1 (5)	C252—C253—C254—C255	0.3 (5)
C153—C154—C155—C156	−0.2 (6)	C253—C254—C255—C256	0.0 (5)
C154—C155—C156—C151	0.2 (5)	C254—C255—C256—C251	0.0 (5)
C152—C151—C156—C155	0.0 (5)	C252—C251—C256—C255	−0.2 (4)
C147—C151—C156—C155	−178.3 (3)	C247—C251—C256—C255	179.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N12	0.98	1.89	2.813 (3)	155
O2—H2A···N22	0.98	1.83	2.774 (3)	160
O1—H1B···N15^i	0.98	2.46	3.114 (3)	124
O2—H2B···N25^ii	0.98	2.54	3.160 (3)	121
N11—H11···N27	0.98	1.90	2.872 (3)	172
N16—H16A···O2	0.98	2.12	3.045 (3)	156
N16—H16B···O1^ii	0.98	2.11	2.988 (3)	148
N21—H21···N17	0.98	1.85	2.828 (3)	172
N26—H26A···O1	0.98	2.00	2.941 (3)	161
N26—H26B···O2^i	0.98	2.08	2.997 (3)	156
C13—H13···Cg2	0.95	2.74	3.472 (3)	134
C23—H23···Cg3	0.95	2.78	3.526 (3)	136
C244—H244···Cg4^iii	0.95	2.65	3.563 (3)	161

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x−1/2, −y+1/2, z−1/2.

(IX) (4-(Pyrrolidin-1-yl)-1/H/-pyrazolo[3,4-/d/]pyrimidin-6-amine) ethanol hemisolvate hemihydrate

Crystal data

2(C9H12N6)·C2H6O·H2O	Z = 2
Mr = 472.58	F(000) = 504
Triclinic, P1	Dx = 1.367 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9342 (15) Å	Cell parameters from 5275 reflections
b = 8.9219 (19) Å	θ = 3.0–27.5°
c = 16.767 (3) Å	µ = 0.10 mm^−1
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) Å^3

Data collection

Bruker-Nonius KappaCCD diffractometer	5275 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3372 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
ϕ & ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003)	h = −10→10
Tmin = 0.967, Tmax = 0.991	k = −11→11
28718 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0811P)^2 + 0.4703P] where P = (Fo^2 + 2Fc^2)/3
5275 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N11	0.4818 (2)	0.17503 (19)	0.42237 (10)	0.0200 (4)
N12	0.4935 (2)	0.29356 (19)	0.35371 (10)	0.0224 (4)
N14	0.2001 (2)	0.58580 (18)	0.50653 (10)	0.0196 (4)
N15	0.2139 (2)	0.35172 (18)	0.59792 (10)	0.0192 (4)
N16	0.2277 (2)	0.12251 (19)	0.69327 (10)	0.0236 (4)
N17	0.3589 (2)	0.12835 (18)	0.56290 (10)	0.0188 (4)
C13	0.4138 (3)	0.4119 (2)	0.37627 (13)	0.0220 (5)
C13A	0.3469 (3)	0.3727 (2)	0.46033 (12)	0.0174 (4)
C14	0.2530 (3)	0.4392 (2)	0.52157 (12)	0.0180 (4)
C16	0.2671 (3)	0.2031 (2)	0.61433 (12)	0.0185 (4)
C17A	0.3944 (3)	0.2189 (2)	0.48712 (12)	0.0187 (4)
C141	0.1108 (3)	0.6551 (2)	0.57069 (12)	0.0202 (4)
C142	0.0618 (3)	0.8156 (2)	0.52534 (13)	0.0232 (5)
C143	0.1870 (3)	0.8511 (2)	0.44775 (13)	0.0239 (5)
C144	0.2326 (3)	0.6952 (2)	0.42737 (13)	0.0220 (5)
N21	0.8747 (2)	0.3347 (2)	0.04059 (10)	0.0234 (4)
N22	0.7905 (2)	0.2106 (2)	0.09043 (11)	0.0271 (4)
N24	0.8217 (2)	−0.00084 (19)	−0.12914 (11)	0.0232 (4)
N25	0.9639 (2)	0.22692 (19)	−0.17981 (10)	0.0208 (4)
N26	1.0936 (2)	0.4576 (2)	−0.23629 (11)	0.0271 (4)
N27	0.9968 (2)	0.41587 (19)	−0.09901 (10)	0.0220 (4)
C23	0.7762 (3)	0.1126 (2)	0.04324 (13)	0.0252 (5)
C23A	0.8510 (3)	0.1703 (2)	−0.03810 (12)	0.0195 (4)
C24	0.8786 (3)	0.1298 (2)	−0.11606 (13)	0.0205 (4)
C26	1.0158 (3)	0.3643 (2)	−0.16940 (13)	0.0208 (4)
C27A	0.9138 (3)	0.3148 (2)	−0.03629 (12)	0.0206 (4)
C241	0.8251 (3)	−0.0333 (3)	−0.21138 (14)	0.0292 (5)
C242	0.6848 (3)	−0.1513 (3)	−0.19921 (15)	0.0347 (6)
C243	0.6924 (3)	−0.2407 (3)	−0.11097 (15)	0.0316 (5)
C244	0.7275 (3)	−0.1167 (2)	−0.06583 (14)	0.0257 (5)
O31	0.5139 (2)	0.25081 (19)	0.76120 (10)	0.0402 (4)
C31	0.4618 (3)	0.2639 (3)	0.84302 (14)	0.0329 (6)
C32	0.5172 (4)	0.4156 (3)	0.85512 (17)	0.0421 (6)
O1	0.77435 (19)	0.22078 (16)	0.25481 (9)	0.0255 (4)
H11	0.5305	0.0876	0.4217	0.024*
H16A	0.1478	0.1588	0.7228	0.028*
H16B	0.2389	0.0240	0.7027	0.028*
H13	0.4026	0.5104	0.3409	0.026*
H41A	0.1858	0.6604	0.6133	0.024*
H41B	0.0089	0.5951	0.5973	0.024*
H42A	0.0715	0.8913	0.5595	0.028*
H42B	−0.0562	0.8175	0.5111	0.028*
H43A	0.2894	0.9014	0.4578	0.029*
H43B	0.1344	0.9199	0.4020	0.029*
H44A	0.1605	0.6736	0.3869	0.026*
H44B	0.3532	0.6915	0.4049	0.026*
H21	0.9017	0.4091	0.0614	0.028*
H26A	1.1142	0.4289	−0.2821	0.033*
H26B	1.1230	0.5485	−0.2343	0.033*
H23	0.7223	0.0155	0.0617	0.030*
H41C	0.9364	−0.0764	−0.2286	0.035*
H41D	0.8007	0.0607	−0.2529	0.035*
H42C	0.5729	−0.1003	−0.2063	0.042*
H42D	0.7069	−0.2195	−0.2384	0.042*
H43C	0.7846	−0.3188	−0.1075	0.038*
H43D	0.5835	−0.2925	−0.0880	0.038*
H44C	0.6204	−0.0731	−0.0439	0.031*
H44D	0.7959	−0.1586	−0.0198	0.031*
H31	0.4334	0.2073	0.7498	0.060*
H31A	0.5123	0.1789	0.8822	0.040*
H31B	0.3368	0.2561	0.8540	0.040*
H32A	0.6401	0.4257	0.8408	0.063*
H32B	0.4884	0.4207	0.9128	0.063*
H32C	0.4593	0.4994	0.8196	0.063*
H1A	0.6810	0.2407	0.2766	0.038*
H1B	0.7659	0.2233	0.2062	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0261 (10)	0.0159 (8)	0.0173 (9)	0.0022 (7)	0.0019 (7)	−0.0047 (7)
N12	0.0293 (10)	0.0191 (9)	0.0175 (9)	0.0006 (7)	0.0013 (7)	−0.0033 (7)
N14	0.0258 (9)	0.0149 (8)	0.0174 (9)	−0.0008 (7)	0.0007 (7)	−0.0040 (7)
N15	0.0239 (9)	0.0147 (8)	0.0184 (9)	−0.0001 (7)	0.0001 (7)	−0.0037 (7)
N16	0.0342 (11)	0.0163 (9)	0.0177 (9)	0.0019 (8)	0.0054 (8)	−0.0026 (7)
N17	0.0224 (9)	0.0154 (8)	0.0174 (9)	−0.0010 (7)	0.0014 (7)	−0.0032 (7)
C13	0.0265 (11)	0.0192 (10)	0.0192 (11)	0.0005 (8)	−0.0011 (9)	−0.0030 (8)
C13A	0.0211 (10)	0.0145 (9)	0.0165 (10)	−0.0018 (8)	−0.0012 (8)	−0.0037 (8)
C14	0.0200 (10)	0.0151 (10)	0.0192 (10)	−0.0021 (8)	−0.0018 (8)	−0.0044 (8)
C16	0.0216 (11)	0.0162 (10)	0.0184 (10)	−0.0025 (8)	−0.0020 (8)	−0.0051 (8)
C17A	0.0195 (10)	0.0183 (10)	0.0192 (10)	−0.0012 (8)	0.0000 (8)	−0.0067 (8)
C141	0.0242 (11)	0.0182 (10)	0.0191 (11)	0.0001 (8)	0.0006 (9)	−0.0074 (8)
C142	0.0285 (12)	0.0171 (10)	0.0246 (11)	0.0016 (9)	−0.0031 (9)	−0.0060 (9)
C143	0.0305 (12)	0.0160 (10)	0.0244 (11)	0.0009 (9)	−0.0001 (9)	−0.0044 (9)
C144	0.0276 (11)	0.0185 (10)	0.0191 (11)	0.0002 (8)	−0.0003 (9)	−0.0034 (8)
N21	0.0327 (11)	0.0209 (9)	0.0180 (9)	−0.0079 (8)	0.0017 (8)	−0.0081 (7)
N22	0.0348 (11)	0.0244 (10)	0.0213 (10)	−0.0073 (8)	0.0021 (8)	−0.0049 (8)
N24	0.0291 (10)	0.0201 (9)	0.0222 (9)	−0.0044 (7)	−0.0015 (8)	−0.0088 (7)
N25	0.0254 (10)	0.0192 (9)	0.0188 (9)	−0.0030 (7)	0.0004 (7)	−0.0072 (7)
N26	0.0412 (12)	0.0208 (9)	0.0202 (10)	−0.0073 (8)	0.0036 (8)	−0.0090 (8)
N27	0.0285 (10)	0.0212 (9)	0.0177 (9)	−0.0026 (8)	0.0007 (8)	−0.0085 (7)
C23	0.0321 (12)	0.0212 (11)	0.0223 (11)	−0.0064 (9)	−0.0006 (9)	−0.0051 (9)
C23A	0.0225 (11)	0.0169 (10)	0.0194 (10)	−0.0017 (8)	−0.0008 (8)	−0.0051 (8)
C24	0.0205 (11)	0.0192 (10)	0.0218 (11)	−0.0003 (8)	−0.0008 (9)	−0.0052 (9)
C26	0.0233 (11)	0.0208 (10)	0.0184 (10)	−0.0010 (8)	−0.0011 (8)	−0.0051 (8)
C27A	0.0226 (11)	0.0206 (10)	0.0194 (11)	−0.0007 (8)	−0.0012 (8)	−0.0064 (8)
C241	0.0356 (13)	0.0314 (12)	0.0238 (12)	−0.0052 (10)	0.0014 (10)	−0.0147 (10)
C242	0.0386 (14)	0.0350 (13)	0.0365 (14)	−0.0097 (11)	−0.0038 (11)	−0.0192 (11)
C243	0.0353 (13)	0.0215 (11)	0.0407 (14)	−0.0056 (10)	−0.0035 (11)	−0.0120 (10)
C244	0.0287 (12)	0.0217 (11)	0.0273 (12)	−0.0051 (9)	−0.0023 (10)	−0.0065 (9)
O31	0.0419 (11)	0.0421 (10)	0.0373 (10)	−0.0078 (8)	−0.0027 (8)	−0.0101 (8)
C31	0.0355 (14)	0.0317 (13)	0.0302 (13)	0.0015 (10)	−0.0057 (11)	−0.0031 (10)
C32	0.0528 (17)	0.0349 (14)	0.0414 (15)	−0.0034 (12)	−0.0102 (13)	−0.0111 (12)
O1	0.0329 (9)	0.0242 (8)	0.0190 (8)	−0.0008 (7)	0.0021 (6)	−0.0067 (6)

Geometric parameters (Å, º)

N11—C17A	1.348 (2)	N24—C244	1.459 (3)
N11—N12	1.371 (2)	N24—C241	1.469 (3)
N11—H11	0.86	N25—C24	1.344 (3)
N12—C13	1.318 (3)	N25—C26	1.360 (3)
N14—C14	1.337 (3)	N26—C26	1.337 (3)
N14—C144	1.460 (3)	N26—H26A	0.86
N14—C141	1.463 (2)	N26—H26B	0.86
N15—C14	1.348 (3)	N27—C27A	1.344 (3)
N15—C16	1.354 (2)	N27—C26	1.353 (3)
N16—C16	1.362 (3)	C23—C23A	1.413 (3)
N16—H16A	0.86	C23—H23	0.95
N16—H16B	0.86	C23A—C27A	1.406 (3)
N17—C16	1.343 (2)	C23A—C24	1.425 (3)
N17—C17A	1.347 (3)	C241—C242	1.524 (3)
C13—C13A	1.418 (3)	C241—H41C	0.99
C13—H13	0.95	C241—H41D	0.99
C13A—C17A	1.396 (3)	C242—C243	1.519 (3)
C13A—C14	1.426 (3)	C242—H42C	0.99
C141—C142	1.521 (3)	C242—H42D	0.99
C141—H41A	0.99	C243—C244	1.524 (3)
C141—H41B	0.99	C243—H43C	0.99
C142—C143	1.524 (3)	C243—H43D	0.99
C142—H42A	0.99	C244—H44C	0.99
C142—H42B	0.99	C244—H44D	0.99
C143—C144	1.528 (3)	O31—C31	1.417 (3)
C143—H43A	0.99	O31—H31	0.82
C143—H43B	0.99	C31—C32	1.500 (3)
C144—H44A	0.99	C31—H31A	0.99
C144—H44B	0.99	C31—H31B	0.99
N21—C27A	1.341 (3)	C32—H32A	0.98
N21—N22	1.370 (2)	C32—H32B	0.98
N21—H21	0.86	C32—H32C	0.98
N22—C23	1.321 (3)	O1—H1A	0.82
N24—C24	1.337 (3)	O1—H1B	0.82
C17A—N11—N12	111.05 (16)	C24—N25—C26	119.30 (17)
C17A—N11—H11	127.6	C26—N26—H26A	121.0
N12—N11—H11	121.3	C26—N26—H26B	120.3
C13—N12—N11	106.16 (16)	H26A—N26—H26B	118.7
C14—N14—C144	124.51 (17)	C27A—N27—C26	112.01 (17)
C14—N14—C141	122.37 (17)	N22—C23—C23A	111.52 (19)
C144—N14—C141	113.03 (15)	N22—C23—H23	124.2
C14—N15—C16	118.66 (17)	C23A—C23—H23	124.2
C16—N16—H16A	117.3	C27A—C23A—C23	104.06 (18)
C16—N16—H16B	117.4	C27A—C23A—C24	115.12 (18)
H16A—N16—H16B	117.0	C23—C23A—C24	140.82 (19)
C16—N17—C17A	112.01 (16)	N24—C24—N25	118.02 (18)
N12—C13—C13A	111.11 (18)	N24—C24—C23A	122.78 (18)
N12—C13—H13	124.4	N25—C24—C23A	119.20 (18)
C13A—C13—H13	124.4	N26—C26—N27	116.94 (18)
C17A—C13A—C13	104.35 (17)	N26—C26—N25	116.04 (18)
C17A—C13A—C14	115.08 (18)	N27—C26—N25	127.02 (18)
C13—C13A—C14	140.57 (18)	N21—C27A—N27	125.65 (18)
N14—C14—N15	117.88 (17)	N21—C27A—C23A	107.05 (18)
N14—C14—C13A	122.73 (18)	N27—C27A—C23A	127.29 (18)
N15—C14—C13A	119.39 (17)	N24—C241—C242	102.75 (17)
N17—C16—N15	127.64 (18)	N24—C241—H41C	111.2
N17—C16—N16	116.66 (17)	C242—C241—H41C	111.2
N15—C16—N16	115.65 (17)	N24—C241—H41D	111.2
N17—C17A—N11	125.47 (18)	C242—C241—H41D	111.2
N17—C17A—C13A	127.19 (18)	H41C—C241—H41D	109.1
N11—C17A—C13A	107.33 (17)	C243—C242—C241	103.15 (19)
N14—C141—C142	104.46 (16)	C243—C242—H42C	111.1
N14—C141—H41A	110.9	C241—C242—H42C	111.1
C142—C141—H41A	110.9	C243—C242—H42D	111.1
N14—C141—H41B	110.9	C241—C242—H42D	111.1
C142—C141—H41B	110.9	H42C—C242—H42D	109.1
H41A—C141—H41B	108.9	C242—C243—C244	103.39 (18)
C141—C142—C143	104.88 (16)	C242—C243—H43C	111.1
C141—C142—H42A	110.8	C244—C243—H43C	111.1
C143—C142—H42A	110.8	C242—C243—H43D	111.1
C141—C142—H42B	110.8	C244—C243—H43D	111.1
C143—C142—H42B	110.8	H43C—C243—H43D	109.0
H42A—C142—H42B	108.8	N24—C244—C243	103.74 (17)
C142—C143—C144	105.28 (16)	N24—C244—H44C	111.0
C142—C143—H43A	110.7	C243—C244—H44C	111.0
C144—C143—H43A	110.7	N24—C244—H44D	111.0
C142—C143—H43B	110.7	C243—C244—H44D	111.0
C144—C143—H43B	110.7	H44C—C244—H44D	109.0
H43A—C143—H43B	108.8	C31—O31—H31	102.8
N14—C144—C143	103.77 (16)	O31—C31—C32	109.9 (2)
N14—C144—H44A	111.0	O31—C31—H31A	109.7
C143—C144—H44A	111.0	C32—C31—H31A	109.7
N14—C144—H44B	111.0	O31—C31—H31B	109.7
C143—C144—H44B	111.0	C32—C31—H31B	109.7
H44A—C144—H44B	109.0	H31A—C31—H31B	108.2
C27A—N21—N22	111.67 (17)	C31—C32—H32A	109.5
C27A—N21—H21	128.8	C31—C32—H32B	109.5
N22—N21—H21	119.4	H32A—C32—H32B	109.5
C23—N22—N21	105.70 (17)	C31—C32—H32C	109.5
C24—N24—C244	124.01 (17)	H32A—C32—H32C	109.5
C24—N24—C241	123.39 (17)	H32B—C32—H32C	109.5
C244—N24—C241	112.03 (16)	H1A—O1—H1B	108.2
C17A—N11—N12—C13	0.4 (2)	C27A—N21—N22—C23	−0.5 (2)
N11—N12—C13—C13A	−0.5 (2)	N21—N22—C23—C23A	0.2 (2)
N12—C13—C13A—C17A	0.3 (2)	N22—C23—C23A—C27A	0.1 (2)
N12—C13—C13A—C14	179.9 (2)	N22—C23—C23A—C24	−179.1 (3)
C144—N14—C14—N15	179.75 (18)	C244—N24—C24—N25	179.96 (18)
C141—N14—C14—N15	3.5 (3)	C241—N24—C24—N25	−9.3 (3)
C144—N14—C14—C13A	−0.7 (3)	C244—N24—C24—C23A	−0.7 (3)
C141—N14—C14—C13A	−177.02 (19)	C241—N24—C24—C23A	170.0 (2)
C16—N15—C14—N14	−179.71 (18)	C26—N25—C24—N24	176.66 (19)
C16—N15—C14—C13A	0.8 (3)	C26—N25—C24—C23A	−2.7 (3)
C17A—C13A—C14—N14	178.94 (19)	C27A—C23A—C24—N24	−177.53 (19)
C13—C13A—C14—N14	−0.6 (4)	C23—C23A—C24—N24	1.6 (4)
C17A—C13A—C14—N15	−1.6 (3)	C27A—C23A—C24—N25	1.8 (3)
C13—C13A—C14—N15	178.9 (2)	C23—C23A—C24—N25	−179.1 (2)
C17A—N17—C16—N15	−1.2 (3)	C27A—N27—C26—N26	178.56 (18)
C17A—N17—C16—N16	−178.57 (18)	C27A—N27—C26—N25	−1.4 (3)
C14—N15—C16—N17	0.7 (3)	C24—N25—C26—N26	−177.31 (18)
C14—N15—C16—N16	178.14 (18)	C24—N25—C26—N27	2.6 (3)
C16—N17—C17A—N11	−178.84 (19)	N22—N21—C27A—N27	−179.72 (19)
C16—N17—C17A—C13A	0.2 (3)	N22—N21—C27A—C23A	0.5 (2)
N12—N11—C17A—N17	178.95 (19)	C26—N27—C27A—N21	−179.3 (2)
N12—N11—C17A—C13A	−0.2 (2)	C26—N27—C27A—C23A	0.4 (3)
C13—C13A—C17A—N17	−179.2 (2)	C23—C23A—C27A—N21	−0.4 (2)
C14—C13A—C17A—N17	1.1 (3)	C24—C23A—C27A—N21	179.04 (18)
C13—C13A—C17A—N11	0.0 (2)	C23—C23A—C27A—N27	179.9 (2)
C14—C13A—C17A—N11	−179.72 (17)	C24—C23A—C27A—N27	−0.7 (3)
C14—N14—C141—C142	−175.13 (19)	C24—N24—C241—C242	−156.0 (2)
C144—N14—C141—C142	8.2 (2)	C244—N24—C241—C242	15.7 (2)
N14—C141—C142—C143	−23.3 (2)	N24—C241—C242—C243	−33.2 (2)
C141—C142—C143—C144	29.8 (2)	C241—C242—C243—C244	38.8 (2)
C14—N14—C144—C143	−166.35 (19)	C24—N24—C244—C243	180.0 (2)
C141—N14—C144—C143	10.2 (2)	C241—N24—C244—C243	8.3 (2)
C142—C143—C144—N14	−24.5 (2)	C242—C243—C244—N24	−29.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N12	0.82	1.97	2.773 (2)	164
O1—H1B···N22	0.82	1.96	2.767 (2)	169
N11—H11···N17^i	0.86	2.06	2.918 (2)	172
N21—H21···N27^ii	0.86	2.03	2.886 (2)	170
N16—H16A···N25^iii	0.86	2.24	3.088 (2)	169
N26—H26A···N15^iv	0.86	2.32	3.172 (3)	171
N16—H16B···O1^i	0.86	2.14	2.988 (2)	168
N26—H26B···O1^ii	0.86	2.18	3.026 (2)	168
O31—H31···N16	0.82	2.21	3.021 (2)	168

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y+1, −z; (iii) x−1, y, z+1; (iv) x+1, y, z−1.