A structural study of new potent and selective antagonists to the A2B adenosine receptor

Ferretti, V.; Pretto, L.; Tabrizi, M.A.; Bertolasi, V.

doi:10.1107/S0108768105021312

A structural study of new potent and selective antagonists to the A_2B adenosine receptor

V. Ferretti, L. Pretto, M. A. Tabrizi and V. Bertolasi

Xanthines, including the natural derivatives theophylline and caffeine, are non-selective antagonists of adenosine. They are able to bind with good affinity to all four adenosine-receptor subtypes A₁, A_2A, A_2B and A₃. In order to develop new drugs with few side effects, over the last few years many efforts have been devoted to the discovery of new adenosine antagonists with enhanced selectivity properties. The present paper reports the crystal structures of five new xanthinic derivatives, which display different affinities and selectivity properties towards the A_2B receptor. Besides the crystallographic study, a structural comparison has been made with the calculated geometry of other xanthinic derivatives which are reported to have similar biological characteristics to understand the structural features controlling their affinity capabilities and selectivity. This structural comparison has been interpreted in the light of a recently published study on the binding of N-benzo[1,3]-dioxol-5-yl-2-[5-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)-1-methyl-1-H-pyrazol-3-iloxy]-acetamide to a model of the A_2B receptor, which shows the most interesting affinity and selectivity properties.

Keywords: adenosine antagonists; affinity; selectivity; xanthines.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768105021312/bk5016sup1.cif Contains datablocks 1, 2, 3, 4, 5
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768105021312/bk50161sup2.hkl Contains datablock 1
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768105021312/bk50162sup3.hkl Contains datablock 2
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768105021312/bk50163sup4.hkl Contains datablock 3
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768105021312/bk50164sup5.hkl Contains datablock 4
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768105021312/bk50165sup6.hkl Contains datablock 5

CCDC references: 286326; 286327; 286328; 286329; 286330

Computing details top

For all compounds, data collection: Kappa CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEPIII(Burnett & Johnson, 1996) for (1), (2); ORTEPIII (Burnett & Johnson, 1996) for (3), (4), (5). Software used to prepare material for publication: SHELXL97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995); WinGX (Farrugia, 1999) for (1), (2); SHELXL97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995) for (3), (4), (5).

Figures top

(1) N-benzo[1,3]-dioxol-5-yl-2-[5-(2,6-dioxo-1,3-dipropyl-2,3,6,9- tetrahydro-1H-purin-8-yl)-1-methyl-1-H-pyrazol-3-iloxy] -acetamide formylhydrazine hydrate top

Crystal data top

C₂₄H₂₇N₇O₆·CH₄N₂O·H₂O	Z = 2
M_r = 587.60	F(000) = 620
Triclinic, P1	D_x = 1.382 Mg m⁻³
a = 7.6900 (2) Å	Mo Kα radiation, λ = 0.71070 Å
b = 9.6995 (2) Å	Cell parameters from 10620 reflections
c = 20.1404 (5) Å	θ = 3.0–28.0°
α = 80.522 (1)°	µ = 0.11 mm⁻¹
β = 86.792 (1)°	T = 295 K
γ = 72.3300 (16)°	Plate, colourless
V = 1411.81 (6) Å³	0.49 × 0.25 × 0.10 mm

Data collection top

Nonius Kappa CCD diffractometer	4559 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 28.0°, θ_min = 3.0°
ϕ scans and ω scans	h = 0→10
10620 measured reflections	k = −11→12
6675 independent reflections	l = −26→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: difference Fourier map
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0591P)² + 0.2999P] where P = (F_o² + 2F_c²)/3
6675 reflections	(Δ/σ)_max = 0.001
477 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₄H₂₇N₇O₆·CH₄N₂O·H₂O	γ = 72.3300 (16)°
M_r = 587.60	V = 1411.81 (6) Å³
Triclinic, P1	Z = 2
a = 7.6900 (2) Å	Mo Kα radiation
b = 9.6995 (2) Å	µ = 0.11 mm⁻¹
c = 20.1404 (5) Å	T = 295 K
α = 80.522 (1)°	0.49 × 0.25 × 0.10 mm
β = 86.792 (1)°

Data collection top

Nonius Kappa CCD diffractometer	4559 reflections with I > 2σ(I)
10620 measured reflections	R_int = 0.034
6675 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.19 e Å⁻³
6675 reflections	Δρ_min = −0.17 e Å⁻³
477 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.8256 (2)	0.14044 (16)	0.92997 (6)	0.0702 (4)
O2	0.74183 (18)	0.41268 (14)	0.71920 (7)	0.0643 (4)
O3	1.36413 (19)	−0.10963 (15)	0.45710 (6)	0.0680 (4)
O4	1.2748 (2)	0.11679 (18)	0.29903 (7)	0.0828 (5)
O5	1.5644 (2)	−0.03418 (17)	0.08609 (6)	0.0734 (4)
O6	1.7774 (2)	−0.26190 (18)	0.08895 (7)	0.0789 (4)
O7	0.90767 (19)	0.33221 (16)	0.55056 (7)	0.0703 (4)
O8	1.0395 (3)	0.3901 (3)	0.33521 (13)	0.1105 (7)
N1	0.78229 (19)	0.27417 (16)	0.82418 (7)	0.0516 (3)
N3	0.9898 (2)	0.03466 (16)	0.84450 (7)	0.0521 (3)
N7	1.00305 (19)	0.14179 (16)	0.67034 (7)	0.0482 (3)
N8	1.13740 (19)	−0.05807 (15)	0.74402 (7)	0.0501 (3)
N9	1.3249 (2)	−0.19901 (16)	0.62635 (7)	0.0549 (4)
N10	1.3904 (2)	−0.23074 (18)	0.56470 (8)	0.0614 (4)
N11	1.4657 (2)	−0.11257 (19)	0.33051 (8)	0.0564 (4)
N12	0.6902 (2)	0.5391 (2)	0.50913 (8)	0.0629 (4)
N13	0.7497 (3)	0.5503 (3)	0.44225 (10)	0.0807 (6)
C2	0.8641 (2)	0.1477 (2)	0.87040 (9)	0.0530 (4)
C4	1.0215 (2)	0.04562 (18)	0.77624 (8)	0.0473 (4)
C5	0.9365 (2)	0.16921 (18)	0.73335 (8)	0.0471 (4)
C6	0.8146 (2)	0.29538 (19)	0.75499 (9)	0.0491 (4)
C9	1.1215 (2)	0.00507 (18)	0.67946 (8)	0.0468 (4)
C10	0.6508 (3)	0.3967 (2)	0.85195 (10)	0.0557 (4)
C11	0.7377 (3)	0.5068 (3)	0.86862 (14)	0.0699 (6)
C12	0.5985 (4)	0.6274 (3)	0.89915 (18)	0.1046 (10)
H121	0.5005	0.6754	0.8680	0.126*
H122	0.6557	0.6972	0.9086	0.126*
H123	0.5512	0.5859	0.9401	0.126*
C13	1.0837 (3)	−0.1010 (2)	0.88966 (10)	0.0569 (4)
C14	0.9903 (4)	−0.2170 (3)	0.89139 (12)	0.0721 (6)
C15	1.0837 (4)	−0.3524 (3)	0.93971 (14)	0.0922 (8)
H151	1.0111	−0.4185	0.9454	0.111*
H152	1.0980	−0.3255	0.9824	0.111*
H153	1.2015	−0.3995	0.9221	0.111*
C16	1.2149 (2)	−0.06043 (19)	0.62242 (8)	0.0476 (4)
C17	1.2068 (2)	0.0026 (2)	0.55538 (9)	0.0523 (4)
C18	1.3183 (2)	−0.1082 (2)	0.52308 (9)	0.0532 (4)
C19	1.3803 (3)	−0.3123 (2)	0.68510 (11)	0.0753 (6)
H191	1.2738	−0.3275	0.7085	0.090*
H192	1.4506	−0.2820	0.7146	0.090*
H193	1.4530	−0.4020	0.6708	0.090*
C20	1.2864 (3)	0.0242 (2)	0.41420 (9)	0.0581 (5)
C21	1.3431 (3)	0.0125 (2)	0.34195 (9)	0.0571 (4)
C22	1.5448 (2)	−0.1517 (2)	0.26805 (8)	0.0511 (4)
C23	1.6725 (3)	−0.2879 (2)	0.27010 (9)	0.0560 (4)
C24	1.7590 (3)	−0.3365 (2)	0.21171 (10)	0.0602 (5)
C25	1.7117 (2)	−0.2432 (2)	0.15291 (9)	0.0557 (4)
C26	1.6735 (4)	−0.1364 (3)	0.04557 (11)	0.0779 (6)
C27	1.5847 (3)	−0.1077 (2)	0.15101 (8)	0.0539 (4)
C28	1.4970 (3)	−0.0566 (2)	0.20716 (9)	0.0555 (4)
C29	0.7690 (3)	0.4333 (2)	0.55677 (11)	0.0643 (5)
H1	1.695 (3)	−0.349 (2)	0.3125 (10)	0.058 (5)*
H2	1.507 (3)	−0.183 (2)	0.3643 (12)	0.068 (6)*
H3	1.083 (3)	−0.079 (2)	0.9356 (12)	0.071 (6)*
H4	1.153 (3)	0.048 (2)	0.4180 (11)	0.075 (6)*
H5	1.140 (3)	0.095 (2)	0.5375 (10)	0.063 (6)*
H6	1.845 (3)	−0.431 (3)	0.2153 (12)	0.080 (7)*
H7	0.978 (3)	0.201 (2)	0.6319 (12)	0.068 (6)*
H8	1.215 (3)	−0.137 (2)	0.8738 (10)	0.067 (6)*
H9	1.597 (4)	−0.168 (3)	0.0213 (15)	0.105 (9)*
H10	1.761 (4)	−0.090 (3)	0.0156 (15)	0.111 (9)*
H11	1.326 (3)	0.104 (2)	0.4272 (10)	0.067 (6)*
H12	1.414 (3)	0.038 (3)	0.2059 (11)	0.071 (6)*
H13	0.547 (3)	0.444 (2)	0.8184 (10)	0.062 (5)*
H14	0.997 (3)	−0.241 (3)	0.8469 (13)	0.081 (7)*
H15	0.850 (4)	−0.172 (3)	0.9076 (14)	0.111 (9)*
H16	0.599 (3)	0.351 (2)	0.8914 (11)	0.068 (6)*
H17	0.789 (3)	0.552 (3)	0.8239 (13)	0.081 (7)*
H18	0.699 (3)	0.437 (3)	0.5998 (13)	0.090 (7)*
H19	0.841 (4)	0.455 (3)	0.8974 (14)	0.098 (8)*
H20	0.593 (4)	0.612 (3)	0.5217 (13)	0.093 (8)*
H21	1.113 (7)	0.306 (6)	0.316 (2)	0.198 (19)*
H22	1.095 (4)	0.452 (3)	0.3149 (15)	0.100*
H23	0.860 (5)	0.566 (4)	0.4443 (18)	0.139 (14)*
H24	0.798 (5)	0.450 (4)	0.4309 (18)	0.138 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0970 (10)	0.0655 (9)	0.0417 (7)	−0.0166 (7)	0.0125 (6)	−0.0091 (6)
O2	0.0763 (8)	0.0492 (8)	0.0513 (7)	0.0027 (6)	−0.0003 (6)	−0.0033 (6)
O3	0.0815 (9)	0.0643 (9)	0.0462 (7)	−0.0046 (7)	0.0158 (6)	−0.0130 (6)
O4	0.1044 (11)	0.0708 (10)	0.0536 (9)	−0.0005 (8)	0.0088 (8)	−0.0067 (8)
O5	0.0956 (10)	0.0740 (10)	0.0398 (7)	−0.0135 (8)	0.0047 (6)	−0.0024 (6)
O6	0.0908 (10)	0.0859 (11)	0.0475 (8)	−0.0083 (8)	0.0135 (7)	−0.0144 (7)
O7	0.0711 (8)	0.0656 (9)	0.0542 (8)	0.0040 (7)	−0.0014 (6)	0.0005 (7)
O8	0.1029 (14)	0.0798 (13)	0.1341 (18)	−0.0136 (11)	0.0310 (12)	−0.0123 (13)
N1	0.0603 (8)	0.0472 (8)	0.0441 (8)	−0.0109 (6)	0.0049 (6)	−0.0101 (6)
N3	0.0682 (9)	0.0451 (8)	0.0373 (7)	−0.0110 (7)	0.0021 (6)	−0.0025 (6)
N7	0.0548 (8)	0.0455 (8)	0.0380 (7)	−0.0068 (6)	0.0007 (6)	−0.0043 (6)
N8	0.0579 (8)	0.0444 (8)	0.0422 (8)	−0.0075 (6)	0.0008 (6)	−0.0056 (6)
N9	0.0582 (8)	0.0495 (9)	0.0468 (8)	−0.0018 (6)	0.0025 (6)	−0.0074 (7)
N10	0.0658 (9)	0.0552 (9)	0.0521 (9)	−0.0009 (7)	0.0078 (7)	−0.0125 (7)
N11	0.0642 (9)	0.0610 (10)	0.0398 (8)	−0.0138 (8)	0.0035 (7)	−0.0065 (7)
N12	0.0610 (9)	0.0614 (10)	0.0527 (9)	0.0009 (8)	−0.0022 (7)	−0.0065 (8)
N13	0.0819 (13)	0.0859 (15)	0.0517 (10)	−0.0015 (11)	0.0021 (9)	0.0076 (10)
C2	0.0660 (10)	0.0498 (10)	0.0425 (9)	−0.0170 (8)	0.0050 (7)	−0.0077 (8)
C4	0.0552 (9)	0.0436 (9)	0.0414 (9)	−0.0124 (7)	0.0015 (7)	−0.0069 (7)
C5	0.0549 (9)	0.0438 (9)	0.0389 (8)	−0.0098 (7)	0.0019 (7)	−0.0061 (7)
C6	0.0540 (9)	0.0460 (10)	0.0442 (9)	−0.0103 (7)	0.0015 (7)	−0.0075 (8)
C9	0.0503 (8)	0.0453 (9)	0.0408 (9)	−0.0087 (7)	0.0005 (6)	−0.0065 (7)
C10	0.0548 (10)	0.0545 (11)	0.0545 (11)	−0.0091 (8)	0.0072 (8)	−0.0157 (9)
C11	0.0643 (12)	0.0631 (13)	0.0849 (16)	−0.0145 (10)	0.0072 (11)	−0.0299 (12)
C12	0.0910 (17)	0.0856 (18)	0.149 (3)	−0.0228 (14)	0.0292 (17)	−0.0674 (19)
C13	0.0693 (12)	0.0542 (11)	0.0429 (10)	−0.0151 (9)	−0.0019 (8)	−0.0014 (8)
C14	0.0949 (17)	0.0634 (13)	0.0590 (13)	−0.0310 (12)	−0.0054 (11)	0.0030 (10)
C15	0.117 (2)	0.0660 (15)	0.0914 (18)	−0.0361 (14)	−0.0141 (15)	0.0152 (13)
C16	0.0471 (8)	0.0461 (9)	0.0451 (9)	−0.0069 (7)	0.0009 (7)	−0.0081 (7)
C17	0.0580 (10)	0.0470 (10)	0.0439 (9)	−0.0052 (8)	0.0044 (7)	−0.0065 (8)
C18	0.0555 (9)	0.0562 (11)	0.0431 (9)	−0.0100 (8)	0.0066 (7)	−0.0094 (8)
C19	0.0900 (14)	0.0543 (12)	0.0579 (12)	0.0090 (10)	−0.0003 (10)	0.0002 (10)
C20	0.0620 (11)	0.0628 (12)	0.0469 (10)	−0.0143 (9)	0.0057 (8)	−0.0112 (9)
C21	0.0626 (10)	0.0621 (12)	0.0467 (10)	−0.0186 (9)	0.0038 (8)	−0.0101 (9)
C22	0.0535 (9)	0.0603 (11)	0.0415 (9)	−0.0203 (8)	0.0032 (7)	−0.0084 (8)
C23	0.0623 (10)	0.0585 (12)	0.0422 (10)	−0.0138 (9)	−0.0003 (8)	−0.0022 (8)
C24	0.0633 (11)	0.0577 (12)	0.0530 (11)	−0.0081 (9)	0.0023 (8)	−0.0095 (9)
C25	0.0590 (10)	0.0654 (12)	0.0439 (9)	−0.0188 (9)	0.0051 (7)	−0.0133 (8)
C26	0.1070 (18)	0.0766 (16)	0.0463 (11)	−0.0220 (14)	0.0091 (12)	−0.0127 (11)
C27	0.0646 (10)	0.0594 (11)	0.0387 (9)	−0.0219 (9)	0.0002 (7)	−0.0040 (8)
C28	0.0627 (10)	0.0554 (11)	0.0448 (10)	−0.0137 (9)	0.0021 (8)	−0.0062 (8)
C29	0.0647 (11)	0.0671 (13)	0.0503 (11)	−0.0055 (10)	−0.0001 (9)	−0.0060 (10)

Geometric parameters (Å, º) top

O1—C2	1.215 (2)	C10—H13	1.02 (2)
O2—C6	1.231 (2)	C10—H16	0.97 (2)
O3—C18	1.357 (2)	C11—C12	1.515 (3)
O3—C20	1.417 (2)	C11—H17	1.04 (2)
O4—C21	1.219 (2)	C11—H19	0.97 (3)
O5—C27	1.375 (2)	C12—H121	0.9600
O5—C26	1.427 (3)	C12—H122	0.9600
O6—C25	1.377 (2)	C12—H123	0.9600
O6—C26	1.422 (3)	C13—C14	1.503 (3)
O7—C29	1.227 (2)	C13—H3	0.98 (2)
O8—H21	0.97 (5)	C13—H8	1.01 (2)
O8—H22	0.87 (3)	C14—C15	1.507 (3)
N1—C6	1.394 (2)	C14—H14	0.96 (3)
N1—C2	1.410 (2)	C14—H15	1.09 (3)
N1—C10	1.474 (2)	C15—H151	0.9600
N3—C4	1.375 (2)	C15—H152	0.9600
N3—C2	1.377 (2)	C15—H153	0.9600
N3—C13	1.478 (2)	C16—C17	1.384 (2)
N7—C9	1.352 (2)	C17—C18	1.386 (2)
N7—C5	1.378 (2)	C17—H5	0.91 (2)
N7—H7	0.88 (2)	C19—H191	0.9600
N8—C9	1.338 (2)	C19—H192	0.9600
N8—C4	1.354 (2)	C19—H193	0.9600
N9—C16	1.346 (2)	C20—C21	1.508 (3)
N9—N10	1.361 (2)	C20—H4	0.98 (2)
N9—C19	1.461 (2)	C20—H11	0.99 (2)
N10—C18	1.322 (2)	C22—C23	1.382 (3)
N11—C21	1.337 (3)	C22—C28	1.401 (3)
N11—C22	1.424 (2)	C23—C24	1.397 (3)
N11—H2	0.88 (2)	C23—H1	0.95 (2)
N12—C29	1.305 (3)	C24—C25	1.360 (3)
N12—N13	1.396 (2)	C24—H6	0.95 (2)
N12—H20	0.92 (3)	C25—C27	1.375 (3)
N13—H23	0.91 (4)	C26—H9	0.93 (3)
N13—H24	0.99 (4)	C26—H10	1.03 (3)
C4—C5	1.363 (2)	C27—C28	1.370 (3)
C5—C6	1.414 (2)	C28—H12	0.94 (2)
C9—C16	1.453 (2)	C29—H18	0.99 (3)
C10—C11	1.508 (3)

C18—O3—C20	114.81 (14)	H3—C13—H8	108.8 (17)
C27—O5—C26	105.38 (16)	C13—C14—C15	111.0 (2)
C25—O6—C26	105.79 (16)	C13—C14—H14	107.1 (14)
H21—O8—H22	97 (3)	C15—C14—H14	109.5 (14)
C6—N1—C2	126.50 (14)	C13—C14—H15	107.6 (15)
C6—N1—C10	116.79 (15)	C15—C14—H15	109.7 (15)
C2—N1—C10	116.70 (15)	H14—C14—H15	112 (2)
C4—N3—C2	119.89 (14)	C14—C15—H151	109.5
C4—N3—C13	120.06 (15)	C14—C15—H152	109.5
C2—N3—C13	119.98 (15)	H151—C15—H152	109.5
C9—N7—C5	106.08 (14)	C14—C15—H153	109.5
C9—N7—H7	126.1 (14)	H151—C15—H153	109.5
C5—N7—H7	127.8 (14)	H152—C15—H153	109.5
C9—N8—C4	103.12 (14)	N9—C16—C17	107.38 (15)
C16—N9—N10	111.51 (14)	N9—C16—C9	124.57 (15)
C16—N9—C19	129.77 (15)	C17—C16—C9	128.03 (16)
N10—N9—C19	118.72 (15)	C16—C17—C18	103.82 (16)
C18—N10—N9	104.27 (14)	C16—C17—H5	126.9 (13)
C21—N11—C22	128.40 (17)	C18—C17—H5	129.2 (13)
C21—N11—H2	119.6 (15)	N10—C18—O3	116.42 (15)
C22—N11—H2	112.0 (15)	N10—C18—C17	113.01 (16)
C29—N12—N13	124.26 (18)	O3—C18—C17	130.56 (17)
C29—N12—H20	116.6 (16)	N9—C19—H191	109.5
N13—N12—H20	119.1 (16)	N9—C19—H192	109.5
N12—N13—H23	104 (2)	H191—C19—H192	109.5
N12—N13—H24	108 (2)	N9—C19—H193	109.5
H23—N13—H24	96 (3)	H191—C19—H193	109.5
O1—C2—N3	122.29 (17)	H192—C19—H193	109.5
O1—C2—N1	121.17 (17)	O3—C20—C21	111.26 (16)
N3—C2—N1	116.54 (15)	O3—C20—H4	107.9 (13)
N8—C4—C5	112.58 (15)	C21—C20—H4	109.3 (13)
N8—C4—N3	126.05 (15)	O3—C20—H11	110.8 (12)
C5—C4—N3	121.36 (15)	C21—C20—H11	107.6 (12)
C4—C5—N7	105.15 (14)	H4—C20—H11	110.1 (18)
C4—C5—C6	123.40 (15)	O4—C21—N11	125.44 (18)
N7—C5—C6	131.39 (15)	O4—C21—C20	117.93 (18)
O2—C6—N1	121.57 (15)	N11—C21—C20	116.62 (17)
O2—C6—C5	126.34 (16)	C23—C22—C28	121.19 (16)
N1—C6—C5	112.09 (15)	C23—C22—N11	116.99 (16)
N8—C9—N7	113.08 (14)	C28—C22—N11	121.82 (17)
N8—C9—C16	126.25 (15)	C22—C23—C24	121.52 (18)
N7—C9—C16	120.66 (15)	C22—C23—H1	117.5 (12)
N1—C10—C11	112.77 (16)	C24—C23—H1	120.9 (12)
N1—C10—H13	108.2 (12)	C25—C24—C23	116.77 (19)
C11—C10—H13	111.6 (11)	C25—C24—H6	124.4 (14)
N1—C10—H16	105.0 (13)	C23—C24—H6	118.8 (14)
C11—C10—H16	112.1 (12)	C24—C25—C27	121.59 (17)
H13—C10—H16	106.8 (16)	C24—C25—O6	128.79 (18)
C10—C11—C12	110.67 (19)	C27—C25—O6	109.61 (16)
C10—C11—H17	107.7 (13)	O6—C26—O5	108.36 (16)
C12—C11—H17	109.6 (13)	O6—C26—H9	106.6 (18)
C10—C11—H19	108.1 (15)	O5—C26—H9	108.8 (18)
C12—C11—H19	113.6 (16)	O6—C26—H10	109.3 (16)
H17—C11—H19	107 (2)	O5—C26—H10	110.0 (16)
C11—C12—H121	109.5	H9—C26—H10	114 (2)
C11—C12—H122	109.5	C28—C27—C25	123.24 (17)
H121—C12—H122	109.5	C28—C27—O5	126.62 (18)
C11—C12—H123	109.5	C25—C27—O5	110.14 (16)
H121—C12—H123	109.5	C27—C28—C22	115.68 (18)
H122—C12—H123	109.5	C27—C28—H12	123.0 (13)
N3—C13—C14	111.75 (17)	C22—C28—H12	121.3 (13)
N3—C13—H3	109.0 (13)	O7—C29—N12	125.9 (2)
C14—C13—H3	108.1 (12)	O7—C29—H18	121.2 (14)
N3—C13—H8	108.3 (12)	N12—C29—H18	112.8 (14)
C14—C13—H8	110.9 (12)

(2) 1,3-diallyl-8-[2-methyl-5-[2-oxo-2-(4-phenylpyperazin-1-yl)-ethoxyl] 2H-pyrazol-3-yl)-3,9-dihydro-purin-2,6-dione top

Crystal data top

C₂₇H₃₀N₈O₄	Z = 2
M_r = 530.59	F(000) = 560
Triclinic, P1	D_x = 1.358 Mg m⁻³
a = 8.7035 (2) Å	Mo Kα radiation, λ = 0.71070 Å
b = 12.4960 (3) Å	Cell parameters from 7632 reflections
c = 13.7034 (3) Å	θ = 3.8–28°
α = 63.416 (1)°	µ = 0.10 mm⁻¹
β = 89.997 (1)°	T = 295 K
γ = 78.2200 (9)°	Plate, colourless
V = 1297.62 (5) Å³	0.44 × 0.15 × 0.09 mm

Data collection top

Nonius Kappa CCD diffractometer	4642 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 28.0°, θ_min = 3.8°
ϕ scans and ω scans	h = −11→11
7632 measured reflections	k = −16→16
6218 independent reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.056P)² + 0.4213P] where P = (F_o² + 2F_c²)/3
6218 reflections	(Δ/σ)_max = 0.004
461 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₇H₃₀N₈O₄	γ = 78.2200 (9)°
M_r = 530.59	V = 1297.62 (5) Å³
Triclinic, P1	Z = 2
a = 8.7035 (2) Å	Mo Kα radiation
b = 12.4960 (3) Å	µ = 0.10 mm⁻¹
c = 13.7034 (3) Å	T = 295 K
α = 63.416 (1)°	0.44 × 0.15 × 0.09 mm
β = 89.997 (1)°

Data collection top

Nonius Kappa CCD diffractometer	4642 reflections with I > 2σ(I)
7632 measured reflections	R_int = 0.025
6218 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.32 e Å⁻³
6218 reflections	Δρ_min = −0.26 e Å⁻³
461 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.27237 (14)	−0.16126 (12)	0.45036 (9)	0.0485 (3)
O2	0.55469 (14)	−0.09589 (14)	0.15485 (9)	0.0606 (4)
O3	−0.02827 (13)	0.33685 (11)	−0.39907 (9)	0.0457 (3)
O4	0.00690 (15)	0.41235 (13)	−0.60598 (10)	0.0519 (3)
N1	0.41247 (15)	−0.12670 (12)	0.30233 (10)	0.0379 (3)
N3	0.13848 (14)	−0.03740 (12)	0.28153 (10)	0.0350 (3)
N7	0.24515 (15)	0.06126 (12)	0.01395 (10)	0.0358 (3)
N8	0.02287 (15)	0.08748 (11)	0.09177 (10)	0.0348 (3)
N9	−0.14346 (15)	0.24737 (12)	−0.13929 (10)	0.0379 (3)
N10	−0.18103 (16)	0.31131 (12)	−0.25061 (10)	0.0401 (3)
N11	−0.25226 (18)	0.49408 (16)	−0.66462 (11)	0.0531 (4)
N12	−0.47374 (16)	0.45336 (13)	−0.78978 (10)	0.0415 (3)
C2	0.27303 (18)	−0.11099 (14)	0.35111 (12)	0.0359 (3)
C4	0.14504 (17)	0.01497 (13)	0.17016 (11)	0.0318 (3)
C5	0.28292 (17)	−0.00329 (14)	0.12610 (11)	0.0342 (3)
C6	0.42702 (18)	−0.07590 (15)	0.18989 (12)	0.0388 (4)
C9	0.08889 (17)	0.11375 (13)	−0.00248 (12)	0.0326 (3)
C10	0.5548 (2)	−0.20260 (19)	0.37843 (14)	0.0512 (5)
C11	0.6352 (3)	−0.1368 (3)	0.4197 (2)	0.0748 (7)
C12	0.5954 (4)	−0.0234 (5)	0.3956 (3)	0.0954 (11)
C13	−0.00770 (19)	−0.01363 (17)	0.32942 (14)	0.0428 (4)
C14	−0.0189 (2)	0.08910 (18)	0.35878 (15)	0.0530 (5)
C15	0.0832 (3)	0.1553 (2)	0.34531 (19)	0.0651 (6)
C16	0.01140 (17)	0.18972 (13)	−0.11291 (12)	0.0337 (3)
C17	0.07899 (19)	0.21614 (15)	−0.20956 (12)	0.0393 (4)
C18	−0.04539 (18)	0.29151 (14)	−0.29068 (12)	0.0360 (3)
C19	−0.2670 (2)	0.25076 (18)	−0.06873 (14)	0.0507 (4)
H191	−0.2336	0.2764	−0.0174	0.061*
H192	−0.2877	0.1703	−0.0295	0.061*
H193	−0.3614	0.3078	−0.1126	0.061*
C20	−0.16675 (19)	0.41297 (16)	−0.47074 (12)	0.0384 (4)
C21	−0.12836 (19)	0.43815 (15)	−0.58603 (12)	0.0391 (3)
C22	−0.2305 (3)	0.5167 (2)	−0.77742 (14)	0.0571 (5)
C23	−0.3065 (2)	0.43441 (19)	−0.80622 (14)	0.0492 (4)
C24	−0.4190 (2)	0.5114 (2)	−0.64752 (15)	0.0536 (5)
C25	−0.4957 (2)	0.43015 (19)	−0.67611 (13)	0.0482 (4)
C26	−0.5699 (2)	0.40344 (15)	−0.83389 (13)	0.0426 (4)
C27	−0.5087 (3)	0.32849 (19)	−0.88163 (17)	0.0567 (5)
C28	−0.6083 (3)	0.2873 (2)	−0.92927 (19)	0.0682 (6)
C29	−0.7676 (3)	0.3191 (2)	−0.93054 (18)	0.0667 (6)
C30	−0.8304 (3)	0.3921 (2)	−0.88229 (19)	0.0635 (5)
C31	−0.7331 (2)	0.43346 (19)	−0.83393 (17)	0.0537 (4)
H1	−0.197 (2)	0.4882 (17)	−0.4660 (14)	0.040 (5)*
H2	0.188 (3)	0.1886 (19)	−0.2165 (17)	0.058 (6)*
H4	0.523 (2)	−0.2704 (19)	0.4402 (18)	0.056 (5)*
H5	−0.430 (2)	0.4955 (18)	−0.5735 (18)	0.057 (6)*
H6	−0.253 (2)	0.3708 (17)	−0.4501 (15)	0.049 (5)*
H7	−0.293 (2)	0.4544 (17)	−0.8830 (17)	0.051 (5)*
H8	−0.445 (3)	0.342 (2)	−0.6234 (18)	0.060 (6)*
H9	0.626 (2)	−0.2384 (18)	0.3384 (17)	0.055 (5)*
H10	−0.471 (3)	0.601 (2)	−0.6961 (19)	0.068 (6)*
H11	−0.095 (3)	0.0025 (19)	0.2763 (18)	0.057 (6)*
H12	−0.012 (2)	−0.0921 (18)	0.3967 (16)	0.049 (5)*
H15	−0.282 (3)	0.609 (2)	−0.831 (2)	0.069 (6)*
H16	−0.835 (3)	0.292 (2)	−0.961 (2)	0.074 (7)*
H17	−0.610 (3)	0.4455 (19)	−0.6679 (18)	0.064 (6)*
H19	−0.123 (3)	0.500 (2)	−0.7853 (18)	0.062 (6)*
H20	0.314 (3)	0.0678 (18)	−0.0403 (17)	0.056 (6)*
H21	−0.251 (2)	0.347 (2)	−0.7632 (17)	0.057 (6)*
H22	−0.782 (3)	0.482 (2)	−0.7970 (18)	0.063 (6)*
H23	−0.562 (3)	0.234 (2)	−0.962 (2)	0.082 (7)*
H24	−0.946 (3)	0.414 (2)	−0.883 (2)	0.079 (7)*
H25	−0.392 (3)	0.299 (2)	−0.8743 (19)	0.074 (7)*
H26	−0.110 (3)	0.103 (2)	0.394 (2)	0.077 (7)*
H27	0.065 (3)	0.220 (2)	0.369 (2)	0.086 (8)*
H28	0.178 (3)	0.143 (3)	0.309 (2)	0.092 (9)*
H29	0.733 (4)	−0.195 (3)	0.476 (3)	0.136 (12)*
H30	0.513 (4)	0.035 (3)	0.341 (2)	0.088 (9)*
H31	0.641 (4)	0.014 (3)	0.422 (3)	0.122 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0424 (6)	0.0612 (7)	0.0268 (5)	−0.0062 (5)	0.0045 (5)	−0.0092 (5)
O2	0.0322 (6)	0.0924 (10)	0.0321 (6)	0.0104 (6)	0.0033 (5)	−0.0170 (6)
O3	0.0365 (6)	0.0600 (7)	0.0278 (5)	0.0051 (5)	−0.0042 (4)	−0.0156 (5)
O4	0.0422 (7)	0.0726 (8)	0.0460 (7)	−0.0081 (6)	0.0043 (5)	−0.0336 (6)
N1	0.0291 (6)	0.0487 (7)	0.0258 (6)	−0.0009 (5)	−0.0001 (5)	−0.0116 (5)
N3	0.0292 (6)	0.0436 (7)	0.0268 (6)	−0.0049 (5)	0.0037 (5)	−0.0127 (5)
N7	0.0310 (6)	0.0436 (7)	0.0262 (6)	0.0000 (5)	−0.0006 (5)	−0.0138 (5)
N8	0.0298 (6)	0.0405 (7)	0.0302 (6)	−0.0042 (5)	−0.0003 (5)	−0.0143 (5)
N9	0.0317 (7)	0.0440 (7)	0.0298 (6)	0.0022 (5)	−0.0015 (5)	−0.0142 (5)
N10	0.0345 (7)	0.0449 (7)	0.0313 (6)	0.0025 (5)	−0.0032 (5)	−0.0140 (6)
N11	0.0457 (8)	0.0801 (11)	0.0289 (7)	−0.0049 (7)	−0.0020 (6)	−0.0248 (7)
N12	0.0416 (7)	0.0496 (8)	0.0294 (6)	−0.0024 (6)	0.0016 (5)	−0.0180 (6)
C2	0.0329 (8)	0.0414 (8)	0.0297 (7)	−0.0082 (6)	0.0036 (6)	−0.0132 (6)
C4	0.0300 (7)	0.0354 (7)	0.0275 (7)	−0.0056 (5)	0.0009 (5)	−0.0131 (6)
C5	0.0309 (7)	0.0418 (8)	0.0255 (6)	−0.0036 (6)	0.0013 (5)	−0.0134 (6)
C6	0.0305 (8)	0.0494 (9)	0.0279 (7)	−0.0004 (6)	0.0013 (6)	−0.0138 (6)
C9	0.0293 (7)	0.0361 (7)	0.0311 (7)	−0.0037 (6)	−0.0014 (5)	−0.0157 (6)
C10	0.0331 (8)	0.0690 (12)	0.0288 (8)	0.0032 (8)	−0.0018 (6)	−0.0090 (8)
C11	0.0456 (12)	0.122 (2)	0.0570 (13)	−0.0229 (13)	−0.0016 (9)	−0.0397 (14)
C12	0.0646 (18)	0.156 (4)	0.115 (3)	−0.053 (2)	0.0241 (18)	−0.094 (3)
C13	0.0323 (8)	0.0551 (10)	0.0346 (8)	−0.0065 (7)	0.0092 (6)	−0.0165 (7)
C14	0.0506 (11)	0.0580 (11)	0.0411 (9)	0.0015 (9)	0.0091 (8)	−0.0204 (8)
C15	0.0761 (16)	0.0571 (12)	0.0619 (13)	−0.0041 (11)	0.0037 (11)	−0.0317 (10)
C16	0.0294 (7)	0.0369 (7)	0.0324 (7)	−0.0025 (6)	−0.0029 (5)	−0.0160 (6)
C17	0.0292 (8)	0.0504 (9)	0.0308 (7)	−0.0005 (6)	−0.0024 (6)	−0.0156 (7)
C18	0.0326 (7)	0.0415 (8)	0.0292 (7)	−0.0019 (6)	−0.0027 (6)	−0.0149 (6)
C19	0.0389 (9)	0.0587 (10)	0.0403 (9)	0.0068 (8)	0.0069 (7)	−0.0179 (8)
C20	0.0340 (8)	0.0454 (9)	0.0289 (7)	0.0017 (7)	−0.0055 (6)	−0.0154 (6)
C21	0.0404 (9)	0.0451 (8)	0.0326 (7)	−0.0057 (7)	−0.0006 (6)	−0.0201 (7)
C22	0.0538 (12)	0.0884 (15)	0.0298 (8)	−0.0190 (11)	0.0043 (8)	−0.0264 (9)
C23	0.0460 (10)	0.0664 (12)	0.0326 (8)	−0.0063 (8)	0.0074 (7)	−0.0230 (8)
C24	0.0434 (10)	0.0762 (13)	0.0355 (9)	0.0097 (9)	−0.0077 (7)	−0.0302 (9)
C25	0.0397 (9)	0.0652 (11)	0.0307 (8)	0.0030 (8)	0.0022 (7)	−0.0203 (8)
C26	0.0510 (10)	0.0404 (8)	0.0307 (7)	−0.0071 (7)	0.0056 (7)	−0.0128 (6)
C27	0.0630 (13)	0.0618 (11)	0.0538 (11)	−0.0140 (10)	0.0183 (9)	−0.0339 (9)
C28	0.0907 (18)	0.0740 (14)	0.0666 (13)	−0.0372 (13)	0.0316 (12)	−0.0475 (12)
C29	0.0873 (17)	0.0763 (14)	0.0607 (12)	−0.0494 (13)	0.0237 (11)	−0.0394 (11)
C30	0.0589 (13)	0.0753 (14)	0.0670 (13)	−0.0282 (11)	0.0135 (10)	−0.0364 (11)
C31	0.0515 (11)	0.0585 (11)	0.0573 (11)	−0.0106 (9)	0.0080 (9)	−0.0326 (9)

Geometric parameters (Å, º) top

O1—C2	1.2171 (18)	C13—H11	0.98 (2)
O2—C6	1.2336 (19)	C13—H12	1.010 (19)
O3—C18	1.3530 (18)	C14—C15	1.294 (3)
O3—C20	1.4206 (17)	C14—H26	0.96 (3)
O4—C21	1.220 (2)	C15—H27	0.98 (3)
N1—C6	1.3966 (18)	C15—H28	0.99 (3)
N1—C2	1.4065 (19)	C16—C17	1.377 (2)
N1—C10	1.4686 (19)	C17—C18	1.393 (2)
N3—C4	1.3719 (17)	C17—H2	0.96 (2)
N3—C2	1.3790 (19)	C19—H191	0.9600
N3—C13	1.4689 (19)	C19—H192	0.9600
N7—C9	1.3543 (19)	C19—H193	0.9600
N7—C5	1.3795 (18)	C20—C21	1.518 (2)
N7—H20	0.94 (2)	C20—H1	0.955 (18)
N8—C9	1.3429 (19)	C20—H6	0.98 (2)
N8—C4	1.3569 (18)	C22—C23	1.514 (3)
N9—C16	1.3553 (19)	C22—H15	1.05 (2)
N9—N10	1.3693 (17)	C22—H19	0.93 (2)
N9—C19	1.453 (2)	C23—H7	0.98 (2)
N10—C18	1.326 (2)	C23—H21	0.99 (2)
N11—C21	1.353 (2)	C24—C25	1.504 (3)
N11—C24	1.458 (2)	C24—H5	0.95 (2)
N11—C22	1.461 (2)	C24—H10	1.01 (2)
N12—C26	1.416 (2)	C25—H8	1.01 (2)
N12—C23	1.460 (2)	C25—H17	0.99 (2)
N12—C25	1.471 (2)	C26—C27	1.390 (2)
C4—C5	1.367 (2)	C26—C31	1.393 (3)
C5—C6	1.409 (2)	C27—C28	1.388 (3)
C9—C16	1.449 (2)	C27—H25	1.00 (3)
C10—C11	1.462 (4)	C28—C29	1.360 (4)
C10—H4	0.98 (2)	C28—H23	0.99 (3)
C10—H9	1.00 (2)	C29—C30	1.381 (3)
C11—C12	1.272 (5)	C29—H16	0.92 (3)
C11—H29	1.05 (4)	C30—C31	1.381 (3)
C12—H30	0.95 (3)	C30—H24	0.98 (3)
C12—H31	0.86 (4)	C31—H22	0.98 (2)
C13—C14	1.493 (3)

C18—O3—C20	115.47 (12)	C16—C17—C18	103.99 (14)
C6—N1—C2	126.07 (12)	C16—C17—H2	126.3 (12)
C6—N1—C10	118.09 (13)	C18—C17—H2	129.7 (12)
C2—N1—C10	115.83 (12)	N10—C18—O3	124.08 (13)
C4—N3—C2	119.69 (12)	N10—C18—C17	113.19 (13)
C4—N3—C13	121.63 (12)	O3—C18—C17	122.72 (14)
C2—N3—C13	118.64 (12)	N9—C19—H191	109.5
C9—N7—C5	106.22 (12)	N9—C19—H192	109.5
C9—N7—H20	126.7 (13)	H191—C19—H192	109.5
C5—N7—H20	127.1 (13)	N9—C19—H193	109.5
C9—N8—C4	103.57 (12)	H191—C19—H193	109.5
C16—N9—N10	111.46 (12)	H192—C19—H193	109.5
C16—N9—C19	129.99 (13)	O3—C20—C21	106.85 (13)
N10—N9—C19	118.55 (12)	O3—C20—H1	110.8 (11)
C18—N10—N9	103.87 (12)	C21—C20—H1	110.4 (10)
C21—N11—C24	126.69 (14)	O3—C20—H6	109.6 (11)
C21—N11—C22	120.50 (16)	C21—C20—H6	111.2 (11)
C24—N11—C22	111.22 (14)	H1—C20—H6	108.2 (16)
C26—N12—C23	117.42 (14)	O4—C21—N11	122.70 (15)
C26—N12—C25	115.07 (14)	O4—C21—C20	121.47 (14)
C23—N12—C25	111.09 (13)	N11—C21—C20	115.80 (14)
O1—C2—N3	122.06 (14)	N11—C22—C23	110.57 (16)
O1—C2—N1	120.92 (13)	N11—C22—H15	109.6 (13)
N3—C2—N1	117.01 (12)	C23—C22—H15	109.1 (13)
N8—C4—C5	112.10 (12)	N11—C22—H19	109.8 (14)
N8—C4—N3	126.48 (13)	C23—C22—H19	108.2 (14)
C5—C4—N3	121.41 (13)	H15—C22—H19	109.6 (18)
C4—C5—N7	105.42 (12)	N12—C23—C22	110.06 (16)
C4—C5—C6	123.38 (13)	N12—C23—H7	110.9 (11)
N7—C5—C6	131.21 (14)	C22—C23—H7	108.0 (11)
O2—C6—N1	121.31 (13)	N12—C23—H21	111.6 (12)
O2—C6—C5	126.25 (14)	C22—C23—H21	110.7 (12)
N1—C6—C5	112.43 (13)	H7—C23—H21	105.4 (16)
N8—C9—N7	112.69 (12)	N11—C24—C25	110.96 (15)
N8—C9—C16	127.11 (13)	N11—C24—H5	109.7 (12)
N7—C9—C16	120.20 (13)	C25—C24—H5	110.9 (12)
C11—C10—N1	114.58 (19)	N11—C24—H10	107.5 (13)
C11—C10—H4	109.5 (12)	C25—C24—H10	110.1 (13)
N1—C10—H4	107.5 (12)	H5—C24—H10	107.5 (17)
C11—C10—H9	110.8 (12)	N12—C25—C24	110.24 (16)
N1—C10—H9	106.4 (12)	N12—C25—H8	110.5 (12)
H4—C10—H9	107.8 (17)	C24—C25—H8	107.7 (12)
C12—C11—C10	127.0 (3)	N12—C25—H17	109.3 (13)
C12—C11—H29	120.9 (19)	C24—C25—H17	110.4 (13)
C10—C11—H29	112.1 (19)	H8—C25—H17	108.7 (17)
C11—C12—H30	124.3 (18)	C27—C26—C31	117.84 (18)
C11—C12—H31	127 (2)	C27—C26—N12	122.64 (17)
H30—C12—H31	109 (3)	C31—C26—N12	119.48 (15)
N3—C13—C14	113.11 (15)	C28—C27—C26	120.6 (2)
N3—C13—H11	106.7 (12)	C28—C27—H25	121.1 (14)
C14—C13—H11	111.9 (12)	C26—C27—H25	118.1 (14)
N3—C13—H12	107.7 (11)	C29—C28—C27	121.0 (2)
C14—C13—H12	110.2 (11)	C29—C28—H23	119.8 (15)
H11—C13—H12	106.9 (16)	C27—C28—H23	119.2 (15)
C15—C14—C13	126.93 (19)	C28—C29—C30	119.2 (2)
C15—C14—H26	118.7 (14)	C28—C29—H16	122.1 (16)
C13—C14—H26	114.3 (14)	C30—C29—H16	118.6 (16)
C14—C15—H27	120.2 (16)	C29—C30—C31	120.6 (2)
C14—C15—H28	120.0 (16)	C29—C30—H24	118.8 (15)
H27—C15—H28	120 (2)	C31—C30—H24	120.6 (15)
N9—C16—C17	107.49 (12)	C30—C31—C26	120.73 (19)
N9—C16—C9	125.43 (14)	C30—C31—H22	118.4 (13)
C17—C16—C9	127.09 (14)	C26—C31—H22	120.8 (13)

(3) N-[5-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)-1- methyl-1-H-pyrazol-3yl]2-phenyl acetamide top

Crystal data top

C₂₃H₂₇N₇O₃	F(000) = 1904
M_r = 449.52	D_x = 1.369 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 33.9318 (5) Å	Cell parameters from 8460 reflections
b = 5.0250 (1) Å	θ = 4.0–28.0°
c = 30.4072 (6) Å	µ = 0.10 mm⁻¹
β = 122.6890 (8)°	T = 150 K
V = 4363.47 (14) Å³	Plate, colourless
Z = 8	0.32 × 0.25 × 0.07 mm

Data collection top

Nonius Kappa CCD diffractometer	3001 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Graphite monochromator	θ_max = 27.5°, θ_min = 2.4°
ϕ scans and ω scans	h = −43→44
8460 measured reflections	k = −5→6
4960 independent reflections	l = −38→38

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: difference Fourier map
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0589P)² + 2.0736P] where P = (F_o² + 2F_c²)/3
4960 reflections	(Δ/σ)_max = 0.006
402 parameters	Δρ_max = 0.33 e Å⁻³
28 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₃H₂₇N₇O₃	V = 4363.47 (14) Å³
M_r = 449.52	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 33.9318 (5) Å	µ = 0.10 mm⁻¹
b = 5.0250 (1) Å	T = 150 K
c = 30.4072 (6) Å	0.32 × 0.25 × 0.07 mm
β = 122.6890 (8)°

Data collection top

Nonius Kappa CCD diffractometer	3001 reflections with I > 2σ(I)
8460 measured reflections	R_int = 0.043
4960 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	28 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.33 e Å⁻³
4960 reflections	Δρ_min = −0.29 e Å⁻³
402 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O2	0.21768 (5)	0.4859 (3)	0.45745 (5)	0.0311 (3)
O1	0.09733 (5)	−0.0462 (3)	0.43246 (6)	0.0377 (4)
O3	0.30841 (5)	1.6053 (3)	0.66333 (5)	0.0332 (4)
N1	0.15651 (5)	0.2279 (3)	0.44446 (6)	0.0261 (4)
N3	0.12327 (5)	0.2690 (3)	0.49559 (6)	0.0262 (4)
N7	0.21244 (5)	0.7482 (3)	0.54642 (6)	0.0239 (4)
N9	0.19539 (5)	0.9822 (3)	0.65061 (6)	0.0252 (4)
N10	0.21822 (5)	1.1731 (3)	0.68804 (6)	0.0263 (4)
N11	0.27561 (5)	1.4953 (3)	0.70902 (6)	0.0241 (4)
N8	0.15720 (5)	0.6167 (3)	0.56112 (6)	0.0247 (4)
C2	0.12398 (6)	0.1381 (4)	0.45606 (8)	0.0277 (5)
C4	0.15463 (6)	0.4707 (4)	0.52213 (7)	0.0229 (4)
C5	0.18763 (6)	0.5440 (4)	0.51184 (7)	0.0227 (4)
C6	0.19030 (6)	0.4276 (4)	0.47083 (7)	0.0245 (4)
C9	0.19317 (6)	0.7832 (4)	0.57529 (7)	0.0233 (4)
C10	0.15328 (8)	0.1125 (5)	0.39793 (8)	0.0325 (5)
C11	0.12726 (7)	0.2956 (5)	0.35092 (8)	0.0422 (6)
H111	0.1446	0.4606	0.3586	0.051*
H112	0.1262	0.2130	0.3215	0.051*
C12	0.07761 (8)	0.3595 (7)	0.33532 (10)	0.0646 (8)
H121	0.0783	0.4514	0.3634	0.077*
H122	0.0602	0.1973	0.3279	0.077*
H123	0.0629	0.4703	0.3048	0.077*
C13	0.08783 (8)	0.1938 (5)	0.50687 (11)	0.0397 (6)
C16	0.21038 (6)	0.9760 (4)	0.61723 (7)	0.0226 (4)
C17	0.24361 (6)	1.1739 (4)	0.63270 (7)	0.0236 (4)
C18	0.24703 (6)	1.2883 (4)	0.67640 (7)	0.0226 (4)
C19	0.16081 (7)	0.8181 (4)	0.65247 (8)	0.0337 (5)
H191	0.1306	0.8454	0.6212	0.040*
H192	0.1598	0.8670	0.6823	0.040*
H193	0.1694	0.6340	0.6551	0.040*
C20	0.30536 (6)	1.6407 (4)	0.70097 (7)	0.0249 (4)
C21	0.33458 (7)	1.8461 (4)	0.74237 (8)	0.0277 (5)
C22	0.38633 (7)	1.7797 (4)	0.77385 (8)	0.0273 (5)
C23	0.40743 (14)	1.7748 (8)	0.82923 (16)	0.0320 (9)	0.50
H23	0.3898	1.8087	0.8437	0.038*	0.50
C25	0.4815 (9)	1.667 (5)	0.8396 (7)	0.039 (3)	0.50
H25	0.5132	1.6248	0.8607	0.046*	0.50
C26	0.45911 (17)	1.6809 (9)	0.7852 (2)	0.0340 (10)	0.50
H26	0.4764	1.6534	0.7701	0.041*	0.50
C27	0.41180 (14)	1.7346 (8)	0.75363 (16)	0.0307 (9)	0.50
H27	0.3976	1.7392	0.7176	0.037*	0.50
C24	0.45491 (15)	1.7182 (9)	0.86075 (17)	0.0397 (11)	0.50
H24	0.4692	1.7145	0.8968	0.048*	0.50
C26A	0.45138 (15)	1.4624 (9)	0.80909 (17)	0.0388 (11)	0.50
H26A	0.4623	1.2880	0.8159	0.047*	0.50
C25A	0.4823 (9)	1.677 (5)	0.8255 (6)	0.047 (3)	0.50
H25A	0.5143	1.6445	0.8432	0.056*	0.50
C27A	0.40422 (14)	1.5179 (8)	0.78242 (16)	0.0315 (9)	0.50
H27A	0.3832	1.3767	0.7694	0.038*	0.50
C23A	0.41967 (14)	1.9809 (9)	0.78988 (18)	0.0370 (10)	0.50
H23A	0.4096	2.1566	0.7824	0.044*	0.50
C24A	0.46720 (16)	1.9293 (10)	0.8164 (2)	0.0499 (13)	0.50
H24A	0.4885	2.0690	0.8279	0.060*	0.50
C14A	0.0499 (3)	0.3690 (19)	0.4905 (5)	0.094 (3)	0.475 (6)
H141	0.0278	0.2701	0.4951	0.112*	0.475 (6)
H142	0.0621	0.5084	0.5167	0.112*	0.475 (6)
C15A	0.0265 (3)	0.482 (2)	0.4499 (5)	0.141 (6)	0.475 (6)
H151	0.0127	0.3541	0.4220	0.169*	0.475 (6)
H152	0.0457	0.6026	0.4450	0.169*	0.475 (6)
H153	0.0022	0.5792	0.4500	0.169*	0.475 (6)
C14	0.03861 (18)	0.3097 (15)	0.4604 (2)	0.051 (2)	0.525 (6)
H143	0.0401	0.5026	0.4618	0.061*	0.525 (6)
H144	0.0340	0.2554	0.4273	0.061*	0.525 (6)
C15	−0.00150 (16)	0.2248 (11)	0.4619 (2)	0.0575 (17)	0.525 (6)
H154	−0.0279	0.3360	0.4393	0.069*	0.525 (6)
H155	0.0057	0.2390	0.4970	0.069*	0.525 (6)
H156	−0.0089	0.0433	0.4505	0.069*	0.525 (6)
H1	0.2606 (7)	1.221 (4)	0.6184 (7)	0.029 (5)*
H2	0.0818 (8)	0.002 (5)	0.5002 (9)	0.045 (7)*
H6	0.2393 (9)	0.844 (5)	0.5497 (9)	0.058 (7)*
H7	0.2735 (7)	1.540 (5)	0.7369 (9)	0.040 (6)*
H8	0.1371 (7)	−0.056 (5)	0.3914 (8)	0.035 (6)*
H9	0.1866 (7)	0.085 (4)	0.4081 (7)	0.026 (5)*
H11	0.3230 (7)	1.870 (4)	0.7652 (8)	0.031 (5)*
H20	0.3314 (8)	2.004 (5)	0.7238 (9)	0.045 (7)*
H131	0.1041 (9)	0.226 (5)	0.5462 (10)	0.059 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0348 (8)	0.0341 (8)	0.0333 (8)	−0.0049 (7)	0.0242 (7)	−0.0032 (7)
O1	0.0352 (8)	0.0345 (9)	0.0454 (9)	−0.0106 (7)	0.0231 (7)	−0.0137 (7)
O3	0.0383 (8)	0.0376 (9)	0.0338 (8)	−0.0065 (7)	0.0261 (7)	−0.0087 (7)
N1	0.0265 (9)	0.0272 (9)	0.0265 (9)	−0.0022 (7)	0.0156 (7)	−0.0038 (7)
N3	0.0260 (9)	0.0272 (9)	0.0280 (9)	−0.0039 (7)	0.0164 (7)	−0.0030 (7)
N7	0.0252 (8)	0.0254 (9)	0.0226 (8)	−0.0020 (7)	0.0140 (7)	−0.0009 (7)
N9	0.0305 (9)	0.0231 (9)	0.0264 (9)	−0.0031 (7)	0.0182 (8)	−0.0023 (7)
N10	0.0297 (9)	0.0255 (9)	0.0247 (8)	−0.0005 (7)	0.0153 (7)	−0.0019 (7)
N11	0.0278 (9)	0.0253 (9)	0.0217 (8)	0.0001 (7)	0.0150 (7)	−0.0026 (7)
N8	0.0246 (8)	0.0253 (9)	0.0249 (8)	−0.0002 (7)	0.0138 (7)	0.0004 (7)
C2	0.0253 (10)	0.0265 (11)	0.0307 (11)	−0.0004 (9)	0.0148 (9)	−0.0023 (9)
C4	0.0228 (10)	0.0240 (10)	0.0204 (9)	0.0011 (8)	0.0106 (8)	0.0018 (8)
C5	0.0245 (10)	0.0240 (10)	0.0202 (9)	0.0001 (8)	0.0125 (8)	0.0007 (8)
C6	0.0242 (10)	0.0247 (10)	0.0244 (10)	0.0024 (8)	0.0129 (9)	0.0028 (8)
C9	0.0243 (10)	0.0244 (10)	0.0226 (10)	0.0016 (8)	0.0137 (8)	0.0028 (8)
C10	0.0318 (12)	0.0357 (13)	0.0331 (12)	−0.0035 (10)	0.0195 (10)	−0.0121 (10)
C11	0.0390 (12)	0.0624 (17)	0.0261 (11)	0.0056 (12)	0.0182 (10)	−0.0080 (11)
C12	0.0429 (14)	0.103 (2)	0.0424 (14)	0.0200 (16)	0.0197 (12)	0.0066 (16)
C13	0.0350 (12)	0.0370 (14)	0.0596 (16)	−0.0083 (11)	0.0337 (12)	−0.0097 (12)
C16	0.0247 (10)	0.0233 (10)	0.0211 (9)	0.0049 (8)	0.0134 (8)	0.0036 (8)
C17	0.0239 (10)	0.0265 (11)	0.0226 (10)	0.0006 (8)	0.0140 (9)	0.0013 (8)
C18	0.0218 (9)	0.0224 (10)	0.0231 (9)	0.0021 (8)	0.0119 (8)	0.0010 (8)
C19	0.0426 (12)	0.0326 (12)	0.0376 (12)	−0.0082 (10)	0.0294 (10)	−0.0044 (10)
C20	0.0247 (10)	0.0235 (10)	0.0287 (10)	0.0045 (9)	0.0158 (9)	0.0011 (9)
C21	0.0313 (11)	0.0252 (11)	0.0307 (11)	0.0005 (9)	0.0195 (10)	−0.0026 (9)
C22	0.0306 (11)	0.0198 (10)	0.0290 (11)	−0.0019 (9)	0.0144 (9)	−0.0010 (9)
C23	0.036 (2)	0.025 (2)	0.034 (2)	−0.0016 (18)	0.018 (2)	−0.0015 (19)
C25	0.029 (5)	0.030 (4)	0.039 (6)	0.007 (3)	0.006 (4)	0.015 (5)
C26	0.029 (2)	0.030 (3)	0.042 (3)	−0.002 (2)	0.018 (2)	0.000 (2)
C27	0.033 (2)	0.028 (2)	0.033 (2)	0.0002 (19)	0.0199 (19)	0.0014 (18)
C24	0.042 (3)	0.035 (3)	0.030 (2)	0.001 (2)	0.011 (2)	0.002 (2)
C26A	0.039 (3)	0.030 (2)	0.041 (3)	0.008 (2)	0.018 (2)	0.000 (2)
C25A	0.029 (5)	0.039 (5)	0.062 (11)	−0.003 (4)	0.017 (9)	0.003 (8)
C27A	0.033 (2)	0.024 (2)	0.037 (2)	−0.0031 (18)	0.018 (2)	−0.0019 (19)
C23A	0.032 (2)	0.027 (2)	0.049 (3)	−0.0043 (19)	0.020 (2)	0.001 (2)
C24A	0.030 (2)	0.034 (3)	0.071 (4)	−0.003 (2)	0.018 (2)	−0.006 (2)
C14A	0.065 (5)	0.072 (6)	0.173 (10)	0.017 (5)	0.084 (7)	0.031 (7)
C15A	0.047 (5)	0.183 (11)	0.199 (12)	0.045 (6)	0.070 (6)	0.138 (9)
C14	0.023 (3)	0.089 (5)	0.036 (3)	−0.006 (3)	0.014 (2)	−0.051 (3)
C15	0.042 (3)	0.065 (4)	0.075 (4)	−0.012 (3)	0.038 (3)	−0.013 (3)

Geometric parameters (Å, º) top

O2—C6	1.234 (2)	C19—H192	0.9600
O1—C2	1.220 (2)	C19—H193	0.9600
O3—C20	1.217 (2)	C20—C21	1.512 (3)
N1—C2	1.402 (2)	C21—C22	1.515 (3)
N1—C6	1.404 (2)	C21—H11	0.97 (2)
N1—C10	1.477 (3)	C21—H20	0.94 (3)
N3—C4	1.373 (2)	C22—C27	1.323 (4)
N3—C2	1.382 (3)	C22—C23A	1.394 (5)
N3—C13	1.467 (3)	C22—C27A	1.413 (5)
N7—C9	1.360 (2)	C22—C23	1.431 (4)
N7—C5	1.383 (2)	C23—C24	1.388 (6)
N7—H6	0.99 (3)	C23—H23	0.9300
N9—C16	1.359 (2)	C25—C24	1.388 (16)
N9—N10	1.365 (2)	C25—C26	1.398 (15)
N9—C19	1.460 (2)	C25—H25	0.9300
N10—C18	1.338 (2)	C26—C27	1.381 (6)
N11—C20	1.371 (2)	C26—H26	0.9300
N11—C18	1.403 (3)	C27—H27	0.9300
N11—H7	0.91 (2)	C24—H24	0.9300
N8—C9	1.344 (2)	C26A—C27A	1.376 (6)
N8—C4	1.356 (2)	C26A—C25A	1.40 (3)
C4—C5	1.366 (3)	C26A—H26A	0.9300
C5—C6	1.424 (3)	C25A—C24A	1.34 (3)
C9—C16	1.450 (3)	C25A—H25A	0.9300
C10—C11	1.519 (3)	C27A—H27A	0.9300
C10—H8	0.97 (2)	C23A—C24A	1.383 (6)
C10—H9	1.007 (19)	C23A—H23A	0.9300
C11—C12	1.517 (3)	C24A—H24A	0.9300
C11—H111	0.9700	C14A—C15A	1.189 (10)
C11—H112	0.9700	C14A—H141	0.9700
C12—H121	0.9600	C14A—H142	0.9700
C12—H122	0.9600	C15A—H151	0.9600
C12—H123	0.9600	C15A—H152	0.9600
C13—C14A	1.409 (7)	C15A—H153	0.9600
C13—C14	1.605 (7)	C14—C15	1.450 (7)
C13—H2	0.99 (3)	C14—H143	0.9700
C13—H131	1.02 (3)	C14—H144	0.9700
C16—C17	1.382 (3)	C15—H154	0.9600
C17—C18	1.394 (3)	C15—H155	0.9600
C17—H1	0.92 (2)	C15—H156	0.9600
C19—H191	0.9600

C2—N1—C6	126.66 (16)	C17—C18—N11	130.50 (17)
C2—N1—C10	116.95 (16)	N9—C19—H191	109.5
C6—N1—C10	116.28 (16)	N9—C19—H192	109.5
C4—N3—C2	119.40 (16)	H191—C19—H192	109.5
C4—N3—C13	121.72 (17)	N9—C19—H193	109.5
C2—N3—C13	118.85 (17)	H191—C19—H193	109.5
C9—N7—C5	106.22 (16)	H192—C19—H193	109.5
C9—N7—H6	127.8 (15)	O3—C20—N11	122.33 (18)
C5—N7—H6	126.0 (14)	O3—C20—C21	122.17 (18)
C16—N9—N10	111.44 (15)	N11—C20—C21	115.50 (17)
C16—N9—C19	130.45 (17)	C20—C21—C22	113.01 (17)
N10—N9—C19	118.10 (15)	C20—C21—H11	110.1 (13)
C18—N10—N9	104.50 (14)	C22—C21—H11	110.8 (12)
C20—N11—C18	124.32 (16)	C20—C21—H20	105.3 (14)
C20—N11—H7	117.7 (15)	C22—C21—H20	106.4 (14)
C18—N11—H7	117.9 (15)	H11—C21—H20	111.1 (19)
C9—N8—C4	103.61 (15)	C27—C22—C23A	71.1 (3)
O1—C2—N3	121.15 (18)	C27—C22—C27A	66.6 (3)
O1—C2—N1	122.00 (18)	C23A—C22—C27A	115.1 (3)
N3—C2—N1	116.85 (17)	C27—C22—C23	120.5 (3)
N8—C4—C5	112.40 (17)	C23A—C22—C23	78.8 (3)
N8—C4—N3	125.23 (17)	C27A—C22—C23	82.8 (3)
C5—C4—N3	122.37 (17)	C27—C22—C21	124.7 (2)
C4—C5—N7	105.27 (16)	C23A—C22—C21	120.4 (2)
C4—C5—C6	122.53 (17)	C27A—C22—C21	123.9 (2)
N7—C5—C6	132.11 (17)	C23—C22—C21	114.8 (2)
O2—C6—N1	120.64 (17)	C24—C23—C22	118.2 (4)
O2—C6—C5	127.33 (18)	C24—C23—H23	120.9
N1—C6—C5	112.03 (16)	C22—C23—H23	120.9
N8—C9—N7	112.50 (17)	C24—C25—C26	117.6 (17)
N8—C9—C16	124.23 (16)	C24—C25—H25	121.2
N7—C9—C16	123.27 (17)	C26—C25—H25	121.2
N1—C10—C11	111.61 (18)	C27—C26—C25	121.2 (10)
N1—C10—H8	106.2 (13)	C27—C26—H26	119.4
C11—C10—H8	111.1 (13)	C25—C26—H26	119.4
N1—C10—H9	105.7 (11)	C22—C27—C26	121.0 (4)
C11—C10—H9	111.0 (11)	C22—C27—H27	119.5
H8—C10—H9	111.0 (17)	C26—C27—H27	119.5
C12—C11—C10	113.9 (2)	C25—C24—C23	121.4 (9)
C12—C11—H111	108.8	C25—C24—H24	119.3
C10—C11—H111	108.8	C23—C24—H24	119.3
C12—C11—H112	108.8	C27A—C26A—C25A	117.6 (11)
C10—C11—H112	108.8	C27A—C26A—H26A	121.2
H111—C11—H112	107.7	C25A—C26A—H26A	121.2
C11—C12—H121	109.5	C24A—C25A—C26A	121.8 (19)
C11—C12—H122	109.5	C24A—C25A—H25A	119.1
H121—C12—H122	109.5	C26A—C25A—H25A	119.1
C11—C12—H123	109.5	C26A—C27A—C22	123.0 (4)
H121—C12—H123	109.5	C26A—C27A—H27A	118.5
H122—C12—H123	109.5	C22—C27A—H27A	118.5
C14A—C13—N3	117.6 (4)	C24A—C23A—C22	122.6 (4)
C14A—C13—C14	31.2 (5)	C24A—C23A—H23A	118.7
N3—C13—C14	107.2 (3)	C22—C23A—H23A	118.7
C14A—C13—H2	119.4 (14)	C25A—C24A—C23A	119.6 (12)
N3—C13—H2	108.1 (13)	C25A—C24A—H24A	120.2
C14—C13—H2	100.0 (14)	C23A—C24A—H24A	120.2
C14A—C13—H131	97.3 (15)	C15A—C14A—C13	129.4 (11)
N3—C13—H131	103.8 (14)	C15A—C14A—H141	104.9
C14—C13—H131	128.2 (14)	C13—C14A—H141	104.9
H2—C13—H131	108 (2)	C15A—C14A—H142	104.9
N9—C16—C17	107.16 (16)	C13—C14A—H142	104.9
N9—C16—C9	122.46 (17)	H141—C14A—H142	105.8
C17—C16—C9	130.36 (17)	C15—C14—C13	114.5 (6)
C16—C17—C18	104.70 (17)	C15—C14—H143	108.6
C16—C17—H1	128.8 (13)	C13—C14—H143	108.6
C18—C17—H1	126.5 (13)	C15—C14—H144	108.6
N10—C18—C17	112.18 (17)	C13—C14—H144	108.6
N10—C18—N11	117.31 (16)	H143—C14—H144	107.6

(4) 1-(3-chloro-phenyl)-3-[5-(2,6-dioxo-1,3-dipropyl-2,3,6,9 tetrahydro-1H-purin-8-yl)-1-methyl-1H-pyrazol-3-yl]urea dimethylformamide dihydrate top

Crystal data top

C₂₂H₂₅ClN₈O₃·(H₂O)·C₃H₇NO	Z = 2
M_r = 594.08	F(000) = 628
Triclinic, P1	D_x = 1.329 Mg m⁻³
a = 10.5330 (2) Å	Mo Kα radiation, λ = 0.71070 Å
b = 11.1912 (2) Å	Cell parameters from 11842 reflections
c = 14.2829 (4) Å	θ = 3.4–28°
α = 85.532 (1)°	µ = 0.18 mm⁻¹
β = 81.8420 (11)°	T = 295 K
γ = 63.0190 (13)°	Plate, colourless
V = 1485.02 (6) Å³	0.38 × 0.20 × 0.12 mm

Data collection top

Nonius Kappa CCD diffractometer	4703 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 28.0°, θ_min = 3.4°
ϕ scans and ω scans	h = 0→13
11842 measured reflections	k = −12→14
6870 independent reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.055	Hydrogen site location: difference Fourier map
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0733P)² + 0.4729P] where P = (F_o² + 2F_c²)/3
6870 reflections	(Δ/σ)_max = 0.001
459 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₂H₂₅ClN₈O₃·(H₂O)·C₃H₇NO	γ = 63.0190 (13)°
M_r = 594.08	V = 1485.02 (6) Å³
Triclinic, P1	Z = 2
a = 10.5330 (2) Å	Mo Kα radiation
b = 11.1912 (2) Å	µ = 0.18 mm⁻¹
c = 14.2829 (4) Å	T = 295 K
α = 85.532 (1)°	0.38 × 0.20 × 0.12 mm
β = 81.8420 (11)°

Data collection top

Nonius Kappa CCD diffractometer	4703 reflections with I > 2σ(I)
11842 measured reflections	R_int = 0.034
6870 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.25 e Å⁻³
6870 reflections	Δρ_min = −0.43 e Å⁻³
459 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.33231 (11)	0.42976 (8)	0.00336 (5)	0.0963 (3)
O1	1.16445 (18)	0.12802 (17)	0.80788 (12)	0.0681 (4)
O2	0.8802 (2)	0.39266 (17)	0.58671 (13)	0.0741 (5)
O3	0.52674 (17)	0.14800 (15)	0.28890 (10)	0.0586 (4)
O4	0.4842 (3)	−0.2433 (2)	0.28530 (16)	0.1024 (7)
O5	0.3503 (2)	0.4108 (2)	0.49686 (17)	0.0868 (7)
O6	0.6411 (3)	0.3537 (2)	0.44403 (16)	0.0823 (6)
N1	1.0248 (2)	0.25757 (18)	0.69558 (13)	0.0546 (4)
N3	1.05451 (18)	0.03630 (17)	0.73284 (12)	0.0500 (4)
N7	0.82359 (19)	0.15257 (18)	0.55741 (12)	0.0486 (4)
N8	0.92490 (18)	−0.03728 (17)	0.64197 (11)	0.0487 (4)
N9	0.77085 (18)	−0.14905 (17)	0.53909 (11)	0.0489 (4)
N10	0.69563 (18)	−0.17166 (17)	0.47838 (12)	0.0494 (4)
N11	0.56325 (19)	−0.05578 (18)	0.35510 (12)	0.0496 (4)
N12	0.4456 (2)	0.01721 (19)	0.22526 (13)	0.0562 (5)
N13	0.4507 (3)	−0.4093 (2)	0.23273 (15)	0.0743 (6)
C2	1.0859 (2)	0.1388 (2)	0.74923 (15)	0.0524 (5)
C4	0.9645 (2)	0.0547 (2)	0.66647 (13)	0.0460 (4)
C5	0.9054 (2)	0.1721 (2)	0.61642 (14)	0.0478 (4)
C6	0.9310 (2)	0.2831 (2)	0.62823 (15)	0.0539 (5)
C9	0.8383 (2)	0.0269 (2)	0.57527 (13)	0.0455 (4)
C10	1.0693 (3)	0.3618 (3)	0.7106 (2)	0.0649 (6)
C11	0.9756 (3)	0.4539 (3)	0.7894 (3)	0.0803 (8)
C12	1.0343 (4)	0.5512 (3)	0.8092 (3)	0.1006 (11)
H121	0.9666	0.6169	0.8537	0.121*
H122	1.0493	0.5952	0.7513	0.121*
H123	1.1237	0.5022	0.8350	0.121*
C13	1.1245 (3)	−0.0920 (2)	0.78377 (17)	0.0574 (5)
C14	1.0480 (4)	−0.0923 (4)	0.8802 (2)	0.0869 (9)
C15	1.1309 (5)	−0.2153 (3)	0.9379 (2)	0.1069 (11)
H151	1.0709	−0.2190	0.9942	0.128*
H152	1.2138	−0.2112	0.9550	0.128*
H153	1.1609	−0.2940	0.9013	0.128*
C16	0.7673 (2)	−0.0267 (2)	0.52303 (13)	0.0453 (4)
C17	0.6865 (2)	0.0334 (2)	0.44929 (14)	0.0453 (4)
C18	0.6452 (2)	−0.06046 (19)	0.42462 (13)	0.0439 (4)
C19	0.8411 (3)	−0.2541 (2)	0.60706 (17)	0.0636 (6)
H191	0.8572	−0.2158	0.6593	0.076*
H192	0.9313	−0.3193	0.5772	0.076*
H193	0.7812	−0.2968	0.6296	0.076*
C20	0.5136 (2)	0.0455 (2)	0.28913 (14)	0.0469 (4)
C21	0.3926 (2)	0.0903 (2)	0.14354 (14)	0.0499 (5)
C22	0.3431 (3)	0.0316 (3)	0.08418 (17)	0.0639 (6)
C23	0.2921 (3)	0.0942 (3)	0.00136 (18)	0.0706 (7)
C24	0.2879 (3)	0.2167 (3)	−0.02464 (17)	0.0672 (6)
C25	0.3365 (3)	0.2741 (2)	0.03455 (16)	0.0624 (6)
C26	0.3889 (3)	0.2135 (2)	0.11808 (15)	0.0568 (5)
C27	0.5136 (4)	−0.3615 (3)	0.2814 (2)	0.0832 (9)
C28	0.4893 (5)	−0.5511 (3)	0.2318 (3)	0.1172 (14)
H281	0.5688	−0.6000	0.2674	0.141*
H282	0.5157	−0.5816	0.1678	0.141*
H283	0.4088	−0.5656	0.2597	0.141*
C29	0.3417 (3)	−0.3210 (3)	0.1745 (2)	0.0899 (9)
H291	0.2990	−0.2314	0.1980	0.108*
H292	0.2692	−0.3510	0.1766	0.108*
H293	0.3847	−0.3222	0.1104	0.108*
H1	0.665 (2)	0.114 (2)	0.4240 (16)	0.055 (6)*
H2	0.420 (3)	0.257 (3)	0.1544 (17)	0.065 (7)*
H3	1.178 (3)	0.306 (3)	0.7259 (17)	0.071 (7)*
H4	0.347 (3)	−0.056 (3)	0.1015 (19)	0.081 (8)*
H5	0.554 (3)	−0.128 (3)	0.3479 (18)	0.070 (7)*
H6	0.772 (3)	0.207 (3)	0.5193 (18)	0.063 (7)*
H7	1.223 (3)	−0.108 (3)	0.7893 (19)	0.083 (8)*
H8	0.446 (3)	−0.067 (3)	0.2305 (17)	0.066 (7)*
H10	1.129 (3)	−0.162 (3)	0.7401 (19)	0.075 (7)*
H11	0.259 (3)	0.051 (3)	−0.038 (2)	0.092 (9)*
H12	0.972 (3)	0.395 (3)	0.848 (2)	0.089 (9)*
H13	1.067 (3)	0.414 (3)	0.647 (2)	0.077 (8)*
H14	0.248 (3)	0.261 (3)	−0.082 (2)	0.089 (9)*
H15	0.874 (4)	0.507 (3)	0.769 (2)	0.102 (10)*
H16	0.578 (4)	−0.431 (4)	0.317 (3)	0.107 (11)*
H17	0.960 (4)	−0.084 (4)	0.870 (3)	0.130 (15)*
H18	1.020 (4)	−0.006 (4)	0.911 (3)	0.113 (12)*
H1O	0.343 (4)	0.329 (4)	0.504 (3)	0.124 (12)*
H2O	0.287 (4)	0.463 (4)	0.463 (3)	0.115 (13)*
H3O	0.647 (4)	0.423 (4)	0.454 (2)	0.097 (11)*
H4O	0.539 (6)	0.377 (5)	0.451 (3)	0.162 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1557 (8)	0.0672 (4)	0.0752 (4)	−0.0543 (5)	−0.0409 (5)	0.0248 (3)
O1	0.0795 (11)	0.0704 (11)	0.0701 (10)	−0.0398 (9)	−0.0399 (9)	0.0072 (8)
O2	0.0949 (12)	0.0543 (10)	0.0883 (12)	−0.0397 (9)	−0.0474 (10)	0.0199 (8)
O3	0.0805 (10)	0.0478 (8)	0.0622 (9)	−0.0367 (8)	−0.0315 (8)	0.0095 (7)
O4	0.167 (2)	0.0705 (13)	0.1093 (16)	−0.0789 (15)	−0.0574 (15)	0.0150 (11)
O5	0.1021 (15)	0.0582 (11)	0.1239 (17)	−0.0473 (11)	−0.0619 (14)	0.0266 (11)
O6	0.1008 (16)	0.0549 (11)	0.1036 (15)	−0.0370 (11)	−0.0522 (12)	0.0161 (10)
N1	0.0645 (11)	0.0514 (10)	0.0589 (10)	−0.0315 (9)	−0.0244 (8)	0.0037 (8)
N3	0.0573 (10)	0.0503 (10)	0.0503 (9)	−0.0272 (8)	−0.0233 (8)	0.0063 (7)
N7	0.0566 (10)	0.0475 (10)	0.0482 (9)	−0.0254 (8)	−0.0221 (8)	0.0050 (7)
N8	0.0567 (9)	0.0487 (9)	0.0475 (9)	−0.0265 (8)	−0.0194 (7)	0.0039 (7)
N9	0.0587 (10)	0.0455 (9)	0.0485 (9)	−0.0253 (8)	−0.0211 (7)	0.0056 (7)
N10	0.0600 (10)	0.0448 (9)	0.0498 (9)	−0.0260 (8)	−0.0203 (8)	0.0051 (7)
N11	0.0666 (11)	0.0448 (9)	0.0498 (9)	−0.0322 (9)	−0.0241 (8)	0.0067 (7)
N12	0.0779 (12)	0.0509 (10)	0.0557 (10)	−0.0377 (10)	−0.0329 (9)	0.0118 (8)
N13	0.1141 (18)	0.0612 (13)	0.0674 (12)	−0.0554 (13)	−0.0148 (12)	−0.0003 (10)
C2	0.0574 (12)	0.0542 (12)	0.0523 (11)	−0.0277 (10)	−0.0182 (9)	0.0001 (9)
C4	0.0510 (10)	0.0485 (11)	0.0421 (9)	−0.0233 (9)	−0.0145 (8)	0.0007 (8)
C5	0.0544 (11)	0.0492 (11)	0.0460 (10)	−0.0256 (9)	−0.0173 (8)	0.0019 (8)
C6	0.0608 (12)	0.0508 (12)	0.0564 (12)	−0.0273 (10)	−0.0212 (10)	0.0040 (9)
C9	0.0504 (10)	0.0465 (11)	0.0442 (10)	−0.0241 (9)	−0.0121 (8)	0.0011 (8)
C10	0.0748 (16)	0.0593 (14)	0.0756 (16)	−0.0390 (13)	−0.0248 (13)	0.0013 (12)
C11	0.0788 (18)	0.0704 (18)	0.097 (2)	−0.0336 (15)	−0.0198 (16)	−0.0156 (16)
C12	0.118 (3)	0.0686 (19)	0.128 (3)	−0.0399 (18)	−0.053 (2)	−0.0143 (18)
C13	0.0626 (13)	0.0522 (13)	0.0611 (13)	−0.0249 (11)	−0.0270 (11)	0.0083 (10)
C14	0.099 (2)	0.078 (2)	0.0729 (18)	−0.0331 (18)	−0.0122 (16)	0.0229 (16)
C15	0.162 (3)	0.080 (2)	0.081 (2)	−0.053 (2)	−0.041 (2)	0.0305 (16)
C16	0.0514 (10)	0.0447 (10)	0.0443 (10)	−0.0236 (9)	−0.0138 (8)	0.0015 (8)
C17	0.0543 (11)	0.0431 (11)	0.0453 (10)	−0.0256 (9)	−0.0159 (8)	0.0041 (8)
C18	0.0514 (10)	0.0427 (10)	0.0424 (9)	−0.0239 (8)	−0.0122 (8)	0.0022 (8)
C19	0.0804 (15)	0.0537 (13)	0.0624 (13)	−0.0304 (12)	−0.0340 (12)	0.0151 (10)
C20	0.0547 (11)	0.0460 (11)	0.0466 (10)	−0.0261 (9)	−0.0157 (8)	0.0028 (8)
C21	0.0566 (11)	0.0497 (11)	0.0474 (10)	−0.0243 (9)	−0.0190 (9)	0.0039 (8)
C22	0.0802 (16)	0.0664 (15)	0.0626 (13)	−0.0433 (13)	−0.0307 (12)	0.0092 (11)
C23	0.0853 (17)	0.0805 (18)	0.0613 (14)	−0.0445 (15)	−0.0354 (13)	0.0082 (12)
C24	0.0755 (15)	0.0753 (17)	0.0517 (12)	−0.0308 (13)	−0.0272 (12)	0.0103 (12)
C25	0.0761 (15)	0.0555 (13)	0.0536 (12)	−0.0263 (12)	−0.0182 (11)	0.0085 (10)
C26	0.0749 (14)	0.0510 (12)	0.0506 (11)	−0.0299 (11)	−0.0229 (10)	0.0045 (9)
C27	0.132 (3)	0.0675 (18)	0.0770 (18)	−0.0633 (19)	−0.0396 (18)	0.0149 (14)
C28	0.208 (4)	0.072 (2)	0.102 (2)	−0.082 (3)	−0.050 (3)	0.0059 (17)
C29	0.089 (2)	0.091 (2)	0.098 (2)	−0.0438 (17)	−0.0218 (17)	−0.0084 (17)

Geometric parameters (Å, º) top

Cl1—C25	1.747 (2)	C11—C12	1.535 (4)
O1—C2	1.221 (2)	C11—H12	1.03 (3)
O2—C6	1.234 (3)	C11—H15	1.03 (3)
O3—C20	1.216 (2)	C12—H121	0.9600
O4—C27	1.218 (3)	C12—H122	0.9600
O5—H1O	0.95 (4)	C12—H123	0.9600
O5—H2O	0.85 (4)	C13—C14	1.495 (4)
O6—H3O	0.83 (4)	C13—H7	0.98 (3)
O6—H4O	0.97 (5)	C13—H10	1.02 (3)
N1—C6	1.398 (3)	C14—C15	1.508 (4)
N1—C2	1.404 (3)	C14—H17	0.93 (4)
N1—C10	1.480 (3)	C14—H18	0.99 (4)
N3—C4	1.374 (2)	C15—H151	0.9600
N3—C2	1.375 (3)	C15—H152	0.9600
N3—C13	1.470 (3)	C15—H153	0.9600
N7—C9	1.351 (3)	C16—C17	1.383 (3)
N7—C5	1.380 (2)	C17—C18	1.390 (3)
N7—H6	0.83 (3)	C17—H1	0.88 (2)
N8—C9	1.342 (2)	C19—H191	0.9600
N8—C4	1.357 (2)	C19—H192	0.9600
N9—C16	1.355 (2)	C19—H193	0.9600
N9—N10	1.362 (2)	C21—C26	1.383 (3)
N9—C19	1.452 (3)	C21—C22	1.394 (3)
N10—C18	1.337 (2)	C22—C23	1.374 (3)
N11—C20	1.372 (3)	C22—H4	0.98 (3)
N11—C18	1.389 (2)	C23—C24	1.374 (4)
N11—H5	0.87 (3)	C23—H11	0.96 (3)
N12—C20	1.371 (2)	C24—C25	1.377 (3)
N12—C21	1.402 (3)	C24—H14	0.97 (3)
N12—H8	0.93 (3)	C25—C26	1.382 (3)
N13—C27	1.311 (3)	C26—H2	0.92 (3)
N13—C28	1.449 (4)	C27—H16	0.94 (4)
N13—C29	1.449 (4)	C28—H281	0.9600
C4—C5	1.365 (3)	C28—H282	0.9600
C5—C6	1.412 (3)	C28—H283	0.9600
C9—C16	1.453 (3)	C29—H291	0.9600
C10—C11	1.498 (4)	C29—H292	0.9600
C10—H3	1.07 (3)	C29—H293	0.9600
C10—H13	1.04 (3)

H1O—O5—H2O	108 (3)	C13—C14—C15	112.6 (3)
H3O—O6—H4O	106 (4)	C13—C14—H17	105 (2)
C6—N1—C2	125.91 (17)	C15—C14—H17	113 (3)
C6—N1—C10	118.15 (19)	C13—C14—H18	110 (2)
C2—N1—C10	115.90 (17)	C15—C14—H18	114 (2)
C4—N3—C2	119.13 (17)	H17—C14—H18	101 (3)
C4—N3—C13	122.22 (17)	C14—C15—H151	109.5
C2—N3—C13	118.58 (17)	C14—C15—H152	109.5
C9—N7—C5	106.55 (17)	H151—C15—H152	109.5
C9—N7—H6	125.7 (17)	C14—C15—H153	109.5
C5—N7—H6	127.8 (17)	H151—C15—H153	109.5
C9—N8—C4	103.42 (16)	H152—C15—H153	109.5
C16—N9—N10	111.07 (15)	N9—C16—C17	107.52 (16)
C16—N9—C19	130.80 (17)	N9—C16—C9	124.59 (17)
N10—N9—C19	118.13 (16)	C17—C16—C9	127.89 (18)
C18—N10—N9	104.89 (15)	C16—C17—C18	104.52 (17)
C20—N11—C18	124.83 (17)	C16—C17—H1	127.9 (15)
C20—N11—H5	117.8 (18)	C18—C17—H1	127.5 (15)
C18—N11—H5	116.7 (18)	N10—C18—N11	117.43 (16)
C20—N12—C21	127.94 (18)	N10—C18—C17	112.00 (16)
C20—N12—H8	117.3 (15)	N11—C18—C17	130.57 (18)
C21—N12—H8	114.1 (15)	N9—C19—H191	109.5
C27—N13—C28	122.3 (3)	N9—C19—H192	109.5
C27—N13—C29	120.5 (2)	H191—C19—H192	109.5
C28—N13—C29	117.2 (2)	N9—C19—H193	109.5
O1—C2—N3	121.7 (2)	H191—C19—H193	109.5
O1—C2—N1	120.62 (19)	H192—C19—H193	109.5
N3—C2—N1	117.64 (17)	O3—C20—N12	124.76 (19)
N8—C4—C5	112.39 (16)	O3—C20—N11	123.77 (17)
N8—C4—N3	125.87 (18)	N12—C20—N11	111.46 (17)
C5—C4—N3	121.74 (17)	C26—C21—C22	118.9 (2)
C4—C5—N7	105.01 (17)	C26—C21—N12	124.45 (18)
C4—C5—C6	123.34 (18)	C22—C21—N12	116.64 (19)
N7—C5—C6	131.65 (19)	C23—C22—C21	120.9 (2)
O2—C6—N1	120.70 (19)	C23—C22—H4	120.1 (17)
O2—C6—C5	127.08 (19)	C21—C22—H4	118.9 (17)
N1—C6—C5	112.22 (18)	C22—C23—C24	120.7 (2)
N8—C9—N7	112.64 (16)	C22—C23—H11	119.1 (19)
N8—C9—C16	126.74 (18)	C24—C23—H11	120.2 (19)
N7—C9—C16	120.60 (17)	C23—C24—C25	118.0 (2)
N1—C10—C11	112.3 (2)	C23—C24—H14	119.7 (18)
N1—C10—H3	104.3 (13)	C25—C24—H14	122.3 (18)
C11—C10—H3	111.8 (13)	C24—C25—C26	122.7 (2)
N1—C10—H13	106.9 (14)	C24—C25—Cl1	119.04 (18)
C11—C10—H13	111.4 (15)	C26—C25—Cl1	118.28 (18)
H3—C10—H13	110 (2)	C25—C26—C21	118.8 (2)
C10—C11—C12	110.6 (3)	C25—C26—H2	118.3 (16)
C10—C11—H12	107.7 (17)	C21—C26—H2	122.9 (16)
C12—C11—H12	111.4 (17)	O4—C27—N13	124.9 (3)
C10—C11—H15	108.0 (18)	O4—C27—H16	125 (2)
C12—C11—H15	109.7 (18)	N13—C27—H16	109 (2)
H12—C11—H15	109 (2)	N13—C28—H281	109.5
C11—C12—H121	109.5	N13—C28—H282	109.5
C11—C12—H122	109.5	H281—C28—H282	109.5
H121—C12—H122	109.5	N13—C28—H283	109.5
C11—C12—H123	109.5	H281—C28—H283	109.5
H121—C12—H123	109.5	H282—C28—H283	109.5
H122—C12—H123	109.5	N13—C29—H291	109.5
N3—C13—C14	112.6 (2)	N13—C29—H292	109.5
N3—C13—H7	108.0 (16)	H291—C29—H292	109.5
C14—C13—H7	109.4 (16)	N13—C29—H293	109.5
N3—C13—H10	104.7 (15)	H291—C29—H293	109.5
C14—C13—H10	113.8 (14)	H292—C29—H293	109.5
H7—C13—H10	108 (2)

(5) N-[5-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro- 1H-purin-8-yl)-1-methyl-1H-pyrazol-3-yl]2-phenyl propionamide dihydrate top

Crystal data top

C₂₄H₂₉N₇O₃·2(H₂O)	F(000) = 1064
M_r = 499.57	D_x = 1.263 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71070 Å
a = 10.4021 (3) Å	Cell parameters from 10036 reflections
b = 15.3698 (6) Å	θ = 3.0–27.0°
c = 16.6432 (7) Å	µ = 0.09 mm⁻¹
β = 99.0850 (16)°	T = 295 K
V = 2627.50 (17) Å³	Plate, colourless
Z = 4	0.41 × 0.17 × 0.06 mm

Data collection top

Nonius Kappa CCD diffractometer	3630 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 27.0°, θ_min = 2.8°
ϕ scans and ω scans	h = 0→13
9233 measured reflections	k = −17→19
5660 independent reflections	l = −21→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.065	Hydrogen site location: difference Fourier map
wR(F²) = 0.213	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.1063P)² + 0.5378P] where P = (F_o² + 2F_c²)/3
5660 reflections	(Δ/σ)_max = 0.001
374 parameters	Δρ_max = 0.39 e Å⁻³
3 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₄H₂₉N₇O₃·2(H₂O)	V = 2627.50 (17) Å³
M_r = 499.57	Z = 4
Monoclinic, P2₁/a	Mo Kα radiation
a = 10.4021 (3) Å	µ = 0.09 mm⁻¹
b = 15.3698 (6) Å	T = 295 K
c = 16.6432 (7) Å	0.41 × 0.17 × 0.06 mm
β = 99.0850 (16)°

Data collection top

Nonius Kappa CCD diffractometer	3630 reflections with I > 2σ(I)
9233 measured reflections	R_int = 0.038
5660 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	3 restraints
wR(F²) = 0.213	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.39 e Å⁻³
5660 reflections	Δρ_min = −0.20 e Å⁻³
374 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.98542 (16)	0.21284 (13)	1.30892 (12)	0.0832 (5)
O2	0.69612 (19)	0.42243 (11)	1.20239 (12)	0.0849 (6)
O3	0.19722 (18)	0.31553 (12)	0.83674 (12)	0.0876 (6)
O4	0.40755 (17)	0.42646 (13)	0.86369 (12)	0.0722 (5)
O5	0.41734 (18)	0.42402 (12)	1.03522 (11)	0.0761 (5)
N1	0.83938 (18)	0.31652 (13)	1.25549 (12)	0.0653 (5)
N3	0.80755 (17)	0.16721 (13)	1.22175 (12)	0.0628 (5)
N9	0.35371 (17)	0.08578 (11)	1.02106 (11)	0.0583 (5)
N7	0.54479 (17)	0.27575 (13)	1.10597 (11)	0.0585 (5)
N8	0.61013 (17)	0.13746 (12)	1.12577 (11)	0.0608 (5)
N10	0.24668 (17)	0.08393 (12)	0.96226 (11)	0.0599 (5)
N11	0.13022 (18)	0.18325 (13)	0.87247 (12)	0.0631 (5)
C2	0.8838 (2)	0.23096 (16)	1.26465 (14)	0.0648 (6)
C4	0.6960 (2)	0.19185 (14)	1.17029 (13)	0.0577 (5)
C5	0.6597 (2)	0.27668 (14)	1.16023 (13)	0.0573 (5)
C6	0.7273 (2)	0.34554 (15)	1.20434 (14)	0.0631 (6)
C9	0.5196 (2)	0.19142 (14)	1.08727 (13)	0.0572 (5)
C10	0.9173 (3)	0.3819 (2)	1.3072 (2)	0.0976 (10)
H9	0.9065	0.4382	1.2807	0.117*
H10	1.0086	0.3663	1.3130	0.117*
C13	0.8454 (3)	0.07523 (16)	1.23079 (17)	0.0757 (7)
H131	0.9383	0.0713	1.2498	0.091*
H132	0.8272	0.0468	1.1782	0.091*
C14	0.7734 (4)	0.0287 (2)	1.2900 (3)	0.1142 (12)
H291	0.6818	0.0274	1.2668	0.137*
H292	0.8036	−0.0311	1.2941	0.137*
C15	0.7844 (5)	0.0632 (4)	1.3706 (3)	0.1503 (18)
H321	0.7331	0.0287	1.4017	0.180*
H322	0.7534	0.1221	1.3681	0.180*
H323	0.8739	0.0619	1.3960	0.180*
C16	0.4056 (2)	0.16683 (14)	1.02949 (13)	0.0568 (5)
C17	0.3294 (2)	0.22001 (16)	0.97415 (14)	0.0620 (6)
C18	0.2337 (2)	0.16469 (14)	0.93446 (13)	0.0567 (5)
C19	0.3902 (2)	0.00697 (15)	1.06742 (16)	0.0683 (6)
H191	0.4815	0.0086	1.0886	0.082*
H192	0.3717	−0.0428	1.0326	0.082*
H193	0.3413	0.0031	1.1116	0.082*
C20	0.1170 (2)	0.25661 (15)	0.82775 (15)	0.0639 (6)
C21	−0.0051 (2)	0.26151 (17)	0.76421 (16)	0.0689 (6)
C22	−0.0613 (3)	0.35233 (19)	0.7597 (2)	0.0953 (9)
H251	−0.0801	0.3689	0.8122	0.114*
H252	−0.1400	0.3535	0.7209	0.114*
H253	0.0005	0.3922	0.7432	0.114*
C23	0.0230 (3)	0.2296 (2)	0.68350 (17)	0.0826 (8)
C24	−0.0387 (4)	0.1562 (3)	0.6488 (2)	0.1202 (13)
H300	−0.0945	0.1252	0.6767	0.144*
C26	0.066 (2)	0.1709 (12)	0.527 (2)	0.231 (19)	0.62 (13)
H260	0.0779	0.1531	0.4757	0.277*	0.62 (13)
C26A	0.059 (3)	0.1735 (18)	0.5381 (19)	0.153 (13)	0.38 (13)
H261	0.0676	0.1563	0.4855	0.183*	0.38 (13)
C27	0.1289 (7)	0.2404 (6)	0.5658 (4)	0.195 (3)
H271	0.1893	0.2695	0.5399	0.234*
C28	0.1077 (4)	0.2712 (4)	0.6434 (2)	0.1419 (17)
H281	0.1522	0.3200	0.6663	0.170*
C25	−0.0183 (7)	0.1282 (5)	0.5724 (4)	0.172 (3)
H350	−0.0624	0.0791	0.5502	0.207*
C12	0.9164 (15)	0.4500 (8)	1.4500 (7)	0.270 (8)	0.640 (10)
H121	0.8458	0.4894	1.4531	0.324*	0.640 (10)
H122	0.9898	0.4819	1.4370	0.324*	0.640 (10)
H123	0.9402	0.4213	1.5014	0.324*	0.640 (10)
C12A	0.7749 (15)	0.4378 (13)	1.3920 (9)	0.176 (9)	0.360 (10)
H124	0.7059	0.4198	1.3500	0.212*	0.360 (10)
H125	0.7966	0.4974	1.3835	0.212*	0.360 (10)
H126	0.7471	0.4319	1.4441	0.212*	0.360 (10)
C11	0.8781 (9)	0.3885 (4)	1.3899 (3)	0.190 (3)
H111	0.7837	0.3909	1.3801	0.228*
H112	0.9006	0.3327	1.4156	0.228*
H1	0.338 (2)	0.2800 (17)	0.9669 (16)	0.073 (7)*
H2	0.383 (3)	0.478 (2)	1.047 (2)	0.106 (10)*
H3	0.339 (4)	0.393 (2)	0.856 (2)	0.112 (11)*
H4	0.503 (3)	0.3247 (19)	1.0859 (17)	0.084 (8)*
H5	−0.071 (2)	0.2236 (16)	0.7788 (15)	0.070 (7)*
H6	0.412 (4)	0.488 (3)	0.858 (3)	0.153 (16)*
H7	0.070 (3)	0.1422 (17)	0.8633 (17)	0.078 (8)*
H8	0.4200	0.4259	0.9812	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0615 (10)	0.0983 (13)	0.0821 (12)	0.0056 (9)	−0.0130 (9)	−0.0055 (10)
O2	0.0968 (13)	0.0583 (11)	0.0896 (13)	−0.0060 (8)	−0.0165 (10)	0.0032 (9)
O3	0.0842 (12)	0.0763 (12)	0.0916 (14)	−0.0256 (9)	−0.0189 (10)	0.0218 (10)
O4	0.0618 (10)	0.0585 (11)	0.0935 (13)	0.0020 (8)	0.0032 (8)	−0.0028 (8)
O5	0.0904 (12)	0.0638 (11)	0.0699 (11)	0.0135 (9)	−0.0005 (9)	0.0035 (8)
N1	0.0612 (11)	0.0706 (12)	0.0595 (11)	−0.0077 (9)	−0.0045 (9)	−0.0024 (9)
N3	0.0547 (10)	0.0684 (12)	0.0609 (11)	0.0051 (8)	−0.0041 (8)	−0.0021 (9)
N9	0.0553 (10)	0.0567 (10)	0.0606 (11)	−0.0024 (7)	0.0018 (8)	0.0050 (8)
N7	0.0606 (10)	0.0573 (11)	0.0539 (10)	−0.0008 (8)	−0.0020 (8)	0.0034 (8)
N8	0.0590 (10)	0.0588 (11)	0.0609 (11)	0.0020 (8)	−0.0017 (8)	−0.0009 (8)
N10	0.0571 (10)	0.0564 (11)	0.0635 (11)	−0.0046 (7)	0.0012 (8)	0.0031 (8)
N11	0.0572 (10)	0.0615 (12)	0.0652 (12)	−0.0111 (8)	−0.0068 (9)	0.0061 (9)
C2	0.0577 (12)	0.0775 (15)	0.0573 (13)	−0.0011 (10)	0.0034 (10)	−0.0012 (11)
C4	0.0547 (11)	0.0646 (13)	0.0519 (12)	0.0014 (9)	0.0022 (9)	−0.0003 (9)
C5	0.0560 (11)	0.0625 (13)	0.0502 (11)	−0.0028 (9)	−0.0013 (9)	0.0028 (9)
C6	0.0670 (13)	0.0621 (14)	0.0568 (13)	−0.0055 (10)	−0.0003 (10)	0.0064 (10)
C9	0.0568 (11)	0.0581 (12)	0.0547 (12)	−0.0012 (9)	0.0022 (9)	0.0031 (9)
C10	0.095 (2)	0.0840 (19)	0.100 (2)	−0.0140 (15)	−0.0297 (17)	−0.0141 (16)
C13	0.0688 (14)	0.0723 (16)	0.0793 (17)	0.0141 (11)	−0.0091 (12)	−0.0052 (13)
C14	0.112 (3)	0.087 (2)	0.132 (3)	−0.0053 (18)	−0.014 (2)	0.025 (2)
C15	0.166 (4)	0.186 (5)	0.096 (3)	−0.034 (3)	0.014 (3)	0.038 (3)
C16	0.0583 (11)	0.0564 (12)	0.0538 (12)	−0.0037 (9)	0.0025 (9)	−0.0003 (9)
C17	0.0650 (13)	0.0541 (13)	0.0620 (13)	−0.0073 (10)	−0.0051 (10)	0.0032 (10)
C18	0.0530 (11)	0.0568 (12)	0.0575 (12)	−0.0052 (9)	0.0003 (9)	0.0033 (9)
C19	0.0667 (13)	0.0582 (13)	0.0776 (16)	−0.0002 (10)	0.0036 (11)	0.0113 (11)
C20	0.0603 (12)	0.0631 (13)	0.0643 (14)	−0.0089 (10)	−0.0030 (10)	0.0036 (10)
C21	0.0623 (13)	0.0679 (14)	0.0712 (15)	−0.0046 (11)	−0.0053 (11)	0.0085 (12)
C22	0.0882 (19)	0.086 (2)	0.105 (2)	0.0132 (15)	−0.0047 (16)	0.0085 (17)
C23	0.0703 (15)	0.104 (2)	0.0660 (16)	0.0097 (14)	−0.0120 (12)	0.0030 (15)
C24	0.121 (3)	0.130 (3)	0.100 (3)	0.005 (2)	−0.013 (2)	−0.032 (2)
C26	0.159 (16)	0.42 (5)	0.098 (11)	0.12 (3)	−0.017 (11)	−0.068 (15)
C26A	0.126 (15)	0.26 (3)	0.075 (12)	−0.05 (3)	0.038 (12)	−0.049 (12)
C27	0.148 (5)	0.340 (11)	0.099 (4)	−0.013 (6)	0.031 (3)	−0.011 (5)
C28	0.126 (3)	0.218 (5)	0.081 (2)	−0.028 (3)	0.015 (2)	0.001 (3)
C25	0.169 (5)	0.217 (7)	0.118 (4)	0.026 (5)	−0.018 (4)	−0.075 (4)
C12	0.301 (17)	0.290 (15)	0.197 (12)	−0.027 (12)	−0.027 (11)	−0.137 (11)
C12A	0.167 (14)	0.25 (2)	0.120 (11)	−0.067 (14)	0.058 (10)	−0.092 (13)
C11	0.267 (8)	0.182 (5)	0.102 (3)	0.007 (5)	−0.033 (4)	−0.075 (4)

Geometric parameters (Å, º) top

O1—C2	1.222 (3)	C15—H323	0.9600
O2—C6	1.224 (3)	C16—C17	1.383 (3)
O3—C20	1.224 (3)	C17—C18	1.394 (3)
O4—H3	0.88 (4)	C17—H1	0.94 (3)
O4—H6	0.96 (5)	C19—H191	0.9600
O5—H2	0.94 (3)	C19—H192	0.9600
O5—H8	0.9043 (18)	C19—H193	0.9600
N1—C2	1.394 (3)	C20—C21	1.521 (3)
N1—C6	1.404 (3)	C21—C23	1.501 (4)
N1—C10	1.479 (3)	C21—C22	1.511 (4)
N3—C4	1.382 (3)	C21—H5	0.96 (3)
N3—C2	1.386 (3)	C22—H251	0.9600
N3—C13	1.469 (3)	C22—H252	0.9600
N9—C16	1.356 (3)	C22—H253	0.9600
N9—N10	1.362 (2)	C23—C28	1.348 (5)
N9—C19	1.454 (3)	C23—C24	1.379 (5)
N7—C9	1.349 (3)	C24—C25	1.390 (7)
N7—C5	1.380 (3)	C24—H300	0.9300
N7—H4	0.91 (3)	C26—C27	1.36 (2)
N8—C9	1.340 (3)	C26—C25	1.40 (2)
N8—C4	1.355 (3)	C26—H260	0.9300
N10—C18	1.324 (3)	C26A—C25	1.268 (17)
N11—C20	1.346 (3)	C26A—C27	1.299 (17)
N11—C18	1.398 (3)	C26A—H261	0.9300
N11—H7	0.89 (3)	C27—C28	1.426 (7)
C4—C5	1.360 (3)	C27—H271	0.9300
C5—C6	1.411 (3)	C28—H281	0.9300
C9—C16	1.454 (3)	C25—H350	0.9300
C10—C11	1.499 (8)	C12—C11	1.389 (10)
C10—H9	0.9700	C12—H121	0.9600
C10—H10	0.9700	C12—H122	0.9600
C13—C14	1.509 (5)	C12—H123	0.9600
C13—H131	0.9700	C12A—C11	1.319 (15)
C13—H132	0.9700	C12A—H124	0.9600
C14—C15	1.430 (6)	C12A—H125	0.9600
C14—H291	0.9700	C12A—H126	0.9600
C14—H292	0.9700	C11—H111	0.9700
C15—H321	0.9600	C11—H112	0.9700
C15—H322	0.9600

H3—O4—H6	129 (3)	H191—C19—H192	109.5
H2—O5—H8	105 (2)	N9—C19—H193	109.5
C2—N1—C6	126.53 (19)	H191—C19—H193	109.5
C2—N1—C10	115.8 (2)	H192—C19—H193	109.5
C6—N1—C10	117.6 (2)	O3—C20—N11	123.0 (2)
C4—N3—C2	118.80 (19)	O3—C20—C21	121.8 (2)
C4—N3—C13	120.84 (19)	N11—C20—C21	115.27 (19)
C2—N3—C13	120.36 (19)	C23—C21—C22	112.7 (2)
C16—N9—N10	111.13 (17)	C23—C21—C20	110.3 (2)
C16—N9—C19	130.11 (19)	C22—C21—C20	110.8 (2)
N10—N9—C19	118.63 (17)	C23—C21—H5	106.0 (15)
C9—N7—C5	106.13 (18)	C22—C21—H5	106.7 (15)
C9—N7—H4	130.3 (19)	C20—C21—H5	110.2 (16)
C5—N7—H4	123.3 (19)	C21—C22—H251	109.5
C9—N8—C4	103.43 (18)	C21—C22—H252	109.5
C18—N10—N9	104.95 (16)	H251—C22—H252	109.5
C20—N11—C18	125.34 (19)	C21—C22—H253	109.5
C20—N11—H7	119.5 (18)	H251—C22—H253	109.5
C18—N11—H7	115.2 (18)	H252—C22—H253	109.5
O1—C2—N3	121.3 (2)	C28—C23—C24	118.6 (4)
O1—C2—N1	121.4 (2)	C28—C23—C21	121.5 (3)
N3—C2—N1	117.26 (19)	C24—C23—C21	119.9 (3)
N8—C4—C5	112.23 (19)	C23—C24—C25	120.5 (5)
N8—C4—N3	125.9 (2)	C23—C24—H300	119.7
C5—C4—N3	121.9 (2)	C25—C24—H300	119.7
C4—C5—N7	105.38 (18)	C27—C26—C25	114 (3)
C4—C5—C6	123.3 (2)	C27—C26—H260	122.8
N7—C5—C6	131.1 (2)	C25—C26—H260	122.8
O2—C6—N1	120.9 (2)	C25—C26A—C27	129 (3)
O2—C6—C5	127.0 (2)	C25—C26A—H261	115.4
N1—C6—C5	112.0 (2)	C27—C26A—H261	115.4
N8—C9—N7	112.82 (19)	C26A—C27—C26	8.5 (19)
N8—C9—C16	126.4 (2)	C26A—C27—C28	115.3 (14)
N7—C9—C16	120.74 (19)	C26—C27—C28	123.7 (14)
N1—C10—C11	112.1 (4)	C26A—C27—H271	126.6
N1—C10—H9	109.2	C26—C27—H271	118.1
C11—C10—H9	109.2	C28—C27—H271	118.1
N1—C10—H10	109.2	C23—C28—C27	119.8 (5)
C11—C10—H10	109.2	C23—C28—H281	120.1
H9—C10—H10	107.9	C27—C28—H281	120.1
N3—C13—C14	111.8 (2)	C26A—C25—C24	116.3 (14)
N3—C13—H131	109.3	C26A—C25—C26	7 (2)
C14—C13—H131	109.3	C24—C25—C26	122.8 (14)
N3—C13—H132	109.3	C26A—C25—H350	125.1
C14—C13—H132	109.3	C24—C25—H350	118.6
H131—C13—H132	107.9	C26—C25—H350	118.6
C15—C14—C13	117.6 (3)	C11—C12—H121	109.5
C15—C14—H291	107.9	C11—C12—H122	109.5
C13—C14—H291	107.9	H121—C12—H122	109.5
C15—C14—H292	107.9	C11—C12—H123	109.5
C13—C14—H292	107.9	H121—C12—H123	109.5
H291—C14—H292	107.2	H122—C12—H123	109.5
C14—C15—H321	109.5	C11—C12A—H124	109.5
C14—C15—H322	109.5	C11—C12A—H125	109.5
H321—C15—H322	109.5	H124—C12A—H125	109.5
C14—C15—H323	109.5	C11—C12A—H126	109.5
H321—C15—H323	109.5	H124—C12A—H126	109.5
H322—C15—H323	109.5	H125—C12A—H126	109.5
N9—C16—C17	107.30 (19)	C12A—C11—C12	74.4 (9)
N9—C16—C9	125.24 (19)	C12A—C11—C10	113.8 (9)
C17—C16—C9	127.5 (2)	C12—C11—C10	128.2 (9)
C16—C17—C18	104.2 (2)	C12A—C11—H111	34.6
C16—C17—H1	127.7 (16)	C12—C11—H111	105.2
C18—C17—H1	128.0 (16)	C10—C11—H111	105.2
N10—C18—C17	112.38 (19)	C12A—C11—H112	129.6
N10—C18—N11	118.24 (19)	C12—C11—H112	105.2
C17—C18—N11	129.4 (2)	C10—C11—H112	105.2
N9—C19—H191	109.5	H111—C11—H112	106.0
N9—C19—H192	109.5

Experimental details

	(1)	(2)	(3)	(4)
Crystal data
Chemical formula	C₂₄H₂₇N₇O₆·CH₄N₂O·H₂O	C₂₇H₃₀N₈O₄	C₂₃H₂₇N₇O₃	C₂₂H₂₅ClN₈O₃·(H₂O)·C₃H₇NO
M_r	587.60	530.59	449.52	594.08
Crystal system, space group	Triclinic, P1	Triclinic, P1	Monoclinic, C2/c	Triclinic, P1
Temperature (K)	295	295	150	295
a, b, c (Å)	7.6900 (2), 9.6995 (2), 20.1404 (5)	8.7035 (2), 12.4960 (3), 13.7034 (3)	33.9318 (5), 5.0250 (1), 30.4072 (6)	10.5330 (2), 11.1912 (2), 14.2829 (4)
α, β, γ (°)	80.522 (1), 86.792 (1), 72.3300 (16)	63.416 (1), 89.997 (1), 78.2200 (9)	90, 122.6890 (8), 90	85.532 (1), 81.8420 (11), 63.0190 (13)
V (Å³)	1411.81 (6)	1297.62 (5)	4363.47 (14)	1485.02 (6)
Z	2	2	8	2
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.11	0.10	0.10	0.18
Crystal size (mm)	0.49 × 0.25 × 0.10	0.44 × 0.15 × 0.09	0.32 × 0.25 × 0.07	0.38 × 0.20 × 0.12

Data collection
Diffractometer	Nonius Kappa CCD diffractometer	Nonius Kappa CCD diffractometer	Nonius Kappa CCD diffractometer	Nonius Kappa CCD diffractometer
Absorption correction	–	–	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10620, 6675, 4559	7632, 6218, 4642	8460, 4960, 3001	11842, 6870, 4703
R_int	0.034	0.025	0.043	0.034
(sin θ/λ)_max (Å⁻¹)	0.660	0.661	0.649	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.151, 1.04	0.048, 0.139, 1.07	0.050, 0.131, 1.01	0.055, 0.169, 1.03
No. of reflections	6675	6218	4960	6870
No. of parameters	477	461	402	459
No. of restraints	0	0	28	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17	0.32, −0.26	0.33, −0.29	0.25, −0.43

	(5)
Crystal data
Chemical formula	C₂₄H₂₉N₇O₃·2(H₂O)
M_r	499.57
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	295
a, b, c (Å)	10.4021 (3), 15.3698 (6), 16.6432 (7)
α, β, γ (°)	90, 99.0850 (16), 90
V (Å³)	2627.50 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.41 × 0.17 × 0.06

Data collection
Diffractometer	Nonius Kappa CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9233, 5660, 3630
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.213, 1.03
No. of reflections	5660
No. of parameters	374
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.20

Computer programs: Kappa CCD server software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), ORTEPIII(Burnett & Johnson, 1996), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995); WinGX (Farrugia, 1999), SHELXL97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995).

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Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text