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Over the last few years many efforts have been devoted to the discovery of new adenosine antagonists which can selectively bind to one of the four adenosine receptors, called A1, A2A, A2B and A3, in order to develop new drugs with few side effects. The present paper reports the crystal structures of four newly synthesized antagonists belonging to the chemical class of pyrazolo-triazolo-pyrimidine derivatives, which display good affinity and selectivity properties towards the A2A or A3 receptor subtypes. These molecules assume an overall planar conformation due to the formation of strong intramolecular N—H...N hydrogen bonds. A systematic investigation on molecules containing the ureidic —NH—C(=O,S)—NH—C=N— fragment has shown that the formation of such interactions is a common feature for this class of compounds. The associated energy, evaluated through DFT calculations, is some 50.24 kJ mol−1, leading to the conclusion that the hydrogen bond, and consequently the planar conformation, is retained not only in the solid state but also in solution during the interaction of the molecule with its receptor.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106013966/de5026sup1.cif
Contains datablocks compound1, compound2, compound3, compound4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106013966/de5026compound1sup2.hkl
Contains datablock shelxl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106013966/de5026compound2sup3.hkl
Contains datablock shelxl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106013966/de5026compound3sup4.hkl
Contains datablock shelxl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106013966/de5026compound4sup5.hkl
Contains datablock shelxl

CCDC references: 618457; 618458; 618459; 618460

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); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995); WinGX (Farrugia, 1999).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
(compound1) N-(8-methyl-2-(2-furyl)-8H-pyrazolo(4,3 − e)(1,2,4)triazolo(1,5 − c) pyrimidin-5-yl)N-(2-chloro phenyl)-urea hemihydrate top
Crystal data top
(C18H13O2N8Cl)·0.5(H2O)Z = 4
Mr = 417.82F(000) = 860
Triclinic, P1Dx = 1.470 Mg m3
a = 6.9825 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 15.7877 (3) ÅCell parameters from 14447 reflections
c = 17.8780 (4) Åθ = 3.4–28.0°
α = 100.2320 (9)°µ = 0.24 mm1
β = 95.906 (1)°T = 295 K
γ = 100.567 (1)°Plate, colourless
V = 1887.81 (6) Å30.50 × 0.38 × 0.12 mm
Data collection top
Nonius Kappa CCD
diffractometer
6646 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 28.0°, θmin = 3.4°
ϕ scans and ω scansh = 99
14447 measured reflectionsk = 2020
8951 independent reflectionsl = 2320
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: difference Fourier map
wR(F2) = 0.138All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0603P)2 + 0.4454P]
where P = (Fo2 + 2Fc2)/3
8951 reflections(Δ/σ)max = 0.004
644 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
(C18H13O2N8Cl)·0.5(H2O)γ = 100.567 (1)°
Mr = 417.82V = 1887.81 (6) Å3
Triclinic, P1Z = 4
a = 6.9825 (1) ÅMo Kα radiation
b = 15.7877 (3) ŵ = 0.24 mm1
c = 17.8780 (4) ÅT = 295 K
α = 100.2320 (9)°0.50 × 0.38 × 0.12 mm
β = 95.906 (1)°
Data collection top
Nonius Kappa CCD
diffractometer
6646 reflections with I > 2σ(I)
14447 measured reflectionsRint = 0.022
8951 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.138All H-atom parameters refined
S = 1.06Δρmax = 0.24 e Å3
8951 reflectionsΔρmin = 0.39 e Å3
644 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl1A1.43102 (8)0.15326 (4)0.11049 (3)0.06652 (16)
O1A1.2549 (2)0.08332 (9)0.18577 (7)0.0641 (4)
O2A0.8086 (3)0.34175 (11)0.30714 (10)0.0850 (5)
N1A1.3191 (2)0.09843 (9)0.05552 (8)0.0452 (3)
N2A1.1773 (2)0.03709 (10)0.13468 (9)0.0469 (3)
N3A1.2102 (2)0.05150 (10)0.00587 (8)0.0474 (3)
N4A1.2323 (3)0.08299 (12)0.11996 (9)0.0612 (4)
N5A1.1719 (3)0.15856 (14)0.14585 (10)0.0674 (5)
N6A0.9265 (2)0.30779 (10)0.09818 (10)0.0538 (4)
N7A1.0605 (2)0.17200 (9)0.10361 (8)0.0438 (3)
N8A0.9911 (2)0.21173 (9)0.17879 (9)0.0484 (3)
C1A1.5613 (3)0.30844 (15)0.07282 (15)0.0694 (6)
C2A1.4698 (3)0.22137 (13)0.04530 (11)0.0532 (4)
C3A1.4081 (2)0.18789 (11)0.03313 (10)0.0470 (4)
C4A1.4392 (3)0.24520 (13)0.08369 (13)0.0601 (5)
C5A1.5334 (4)0.33210 (15)0.05563 (18)0.0769 (7)
C6A1.5941 (4)0.36301 (17)0.02195 (18)0.0825 (7)
C7A1.2541 (3)0.05305 (11)0.12798 (10)0.0454 (4)
C8A1.1533 (2)0.08420 (11)0.07802 (10)0.0428 (3)
C9A1.1758 (2)0.10787 (12)0.04448 (10)0.0482 (4)
C10A1.0834 (3)0.22675 (17)0.09110 (13)0.0648 (5)
C11A1.0826 (3)0.19706 (13)0.02267 (11)0.0513 (4)
C12A1.0197 (2)0.23080 (12)0.05636 (11)0.0474 (4)
C13A0.9110 (3)0.29227 (12)0.17102 (11)0.0508 (4)
C14A0.8089 (3)0.36044 (13)0.23538 (13)0.0583 (5)
C15A0.7066 (4)0.44267 (17)0.2402 (2)0.0863 (8)
C16A0.6407 (4)0.4770 (2)0.3193 (2)0.0959 (10)
C17A0.7037 (5)0.4164 (2)0.3569 (2)0.1046 (10)
C18A1.2120 (7)0.1580 (3)0.22779 (16)0.0963 (10)
Cl1B1.26192 (8)0.19635 (4)0.57887 (3)0.07085 (17)
O1B1.2019 (2)0.10078 (9)0.29160 (7)0.0630 (4)
O2B1.2132 (3)0.34083 (10)0.21229 (10)0.0853 (5)
N1B1.2403 (2)0.12592 (10)0.41826 (9)0.0490 (3)
N2B1.2345 (2)0.01441 (10)0.35134 (9)0.0466 (3)
N3B1.2553 (2)0.01477 (10)0.48121 (8)0.0495 (3)
N4B1.2727 (2)0.03008 (12)0.61057 (9)0.0604 (4)
N5B1.2739 (3)0.10048 (14)0.64473 (9)0.0643 (5)
N6B1.2381 (2)0.27758 (11)0.41751 (10)0.0561 (4)
N7B1.2392 (2)0.14404 (9)0.39658 (8)0.0457 (3)
N8B1.2263 (2)0.19225 (10)0.32607 (8)0.0501 (3)
C1B1.2426 (4)0.34635 (18)0.52601 (18)0.0845 (8)
C2B1.2445 (3)0.25781 (14)0.50749 (12)0.0600 (5)
C3B1.2339 (3)0.21655 (12)0.43243 (11)0.0519 (4)
C4B1.2184 (4)0.26806 (15)0.37718 (15)0.0698 (6)
C5B1.2173 (5)0.35703 (17)0.3968 (2)0.0938 (9)
C6B1.2287 (5)0.3958 (2)0.4704 (2)0.1018 (10)
C7B1.2242 (3)0.07485 (11)0.35101 (9)0.0449 (4)
C8B1.2446 (2)0.05523 (11)0.41252 (9)0.0443 (4)
C9B1.2615 (2)0.06397 (13)0.53753 (10)0.0505 (4)
C10B1.2642 (3)0.17460 (17)0.59777 (12)0.0623 (5)
C11B1.2571 (3)0.15396 (13)0.52603 (10)0.0521 (4)
C12B1.2454 (2)0.19698 (13)0.45056 (11)0.0499 (4)
C13B1.2245 (3)0.27075 (12)0.34299 (11)0.0515 (4)
C14B1.2006 (3)0.34565 (13)0.28750 (12)0.0584 (5)
C15B1.1618 (4)0.42370 (16)0.29617 (18)0.0793 (7)
C16B1.1485 (4)0.46979 (18)0.2225 (2)0.0913 (9)
C17B1.1793 (5)0.41877 (18)0.1739 (2)0.0956 (9)
C18B1.2845 (5)0.0894 (3)0.72725 (14)0.0878 (9)
O1W0.8400 (6)0.4518 (2)0.0207 (2)0.1557 (13)
H11.153 (3)0.0637 (14)0.1812 (13)0.058 (6)*
H21.229 (3)0.0432 (14)0.3087 (12)0.054 (6)*
H31.402 (5)0.080 (2)0.7336 (17)0.106 (10)*
H41.399 (3)0.2254 (14)0.1351 (13)0.058 (6)*
H51.164 (6)0.038 (3)0.757 (2)0.146 (14)*
H61.207 (4)0.2492 (19)0.3300 (16)0.092 (9)*
H71.551 (4)0.3677 (19)0.0932 (15)0.092 (8)*
H81.247 (3)0.0988 (15)0.4564 (14)0.070 (7)*
H91.341 (7)0.139 (3)0.244 (2)0.153 (17)*
H101.136 (6)0.127 (3)0.253 (2)0.136 (15)*
H111.303 (3)0.0658 (14)0.0179 (12)0.061 (6)*
H121.653 (4)0.422 (2)0.0436 (17)0.105 (9)*
H131.268 (4)0.2315 (18)0.6170 (15)0.086 (8)*
H141.202 (5)0.386 (2)0.3582 (18)0.102 (10)*
H151.238 (5)0.453 (3)0.483 (2)0.130 (12)*
H161.038 (4)0.2814 (17)0.1059 (14)0.078 (7)*
H171.251 (4)0.3730 (19)0.5787 (17)0.098 (9)*
H180.564 (5)0.534 (2)0.3456 (17)0.109 (10)*
H191.257 (6)0.139 (3)0.745 (2)0.139 (13)*
H201.182 (6)0.423 (2)0.119 (2)0.137 (13)*
H210.698 (5)0.468 (2)0.1985 (18)0.110 (11)*
H221.127 (5)0.524 (2)0.2088 (18)0.111 (10)*
H231.599 (4)0.3296 (16)0.1299 (15)0.075 (7)*
H241.180 (6)0.217 (3)0.235 (2)0.136 (13)*
H251.133 (5)0.434 (2)0.3413 (18)0.106 (11)*
H260.702 (7)0.407 (3)0.416 (3)0.180 (18)*
H2W0.900 (8)0.489 (3)0.049 (3)0.17 (2)*
H1W0.862 (7)0.409 (3)0.060 (3)0.173 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0684 (3)0.0854 (4)0.0451 (2)0.0178 (3)0.0143 (2)0.0055 (2)
O1A0.1004 (11)0.0461 (7)0.0424 (7)0.0056 (7)0.0000 (7)0.0149 (6)
O2A0.1028 (13)0.0652 (10)0.0693 (10)0.0052 (9)0.0025 (9)0.0043 (8)
N1A0.0502 (8)0.0431 (7)0.0412 (7)0.0060 (6)0.0063 (6)0.0097 (6)
N2A0.0604 (9)0.0413 (7)0.0375 (7)0.0070 (6)0.0033 (6)0.0095 (6)
N3A0.0535 (8)0.0513 (8)0.0407 (7)0.0125 (6)0.0120 (6)0.0131 (6)
N4A0.0704 (10)0.0758 (11)0.0445 (8)0.0178 (8)0.0202 (7)0.0215 (8)
N5A0.0733 (11)0.0878 (13)0.0508 (10)0.0161 (10)0.0212 (8)0.0324 (9)
N6A0.0478 (8)0.0495 (8)0.0678 (10)0.0080 (6)0.0101 (7)0.0226 (7)
N7A0.0423 (7)0.0448 (7)0.0459 (7)0.0086 (6)0.0073 (6)0.0132 (6)
N8A0.0503 (8)0.0445 (8)0.0499 (8)0.0081 (6)0.0070 (6)0.0102 (6)
C1A0.0583 (12)0.0632 (13)0.0737 (15)0.0056 (10)0.0056 (10)0.0113 (11)
C2A0.0416 (8)0.0592 (11)0.0556 (10)0.0127 (7)0.0093 (7)0.0008 (8)
C3A0.0391 (8)0.0454 (9)0.0548 (10)0.0082 (7)0.0079 (7)0.0053 (7)
C4A0.0614 (11)0.0492 (10)0.0653 (13)0.0035 (8)0.0017 (9)0.0124 (9)
C5A0.0776 (15)0.0517 (12)0.0967 (19)0.0004 (10)0.0060 (13)0.0193 (12)
C6A0.0771 (15)0.0553 (13)0.098 (2)0.0024 (11)0.0018 (13)0.0075 (13)
C7A0.0529 (9)0.0418 (8)0.0424 (9)0.0096 (7)0.0057 (7)0.0117 (7)
C8A0.0429 (8)0.0433 (8)0.0453 (9)0.0109 (6)0.0094 (6)0.0128 (7)
C9A0.0454 (9)0.0614 (11)0.0455 (9)0.0168 (8)0.0168 (7)0.0188 (8)
C10A0.0625 (12)0.0772 (14)0.0638 (13)0.0108 (10)0.0189 (10)0.0365 (12)
C11A0.0439 (9)0.0625 (11)0.0557 (10)0.0125 (8)0.0156 (7)0.0266 (9)
C12A0.0390 (8)0.0508 (9)0.0591 (10)0.0116 (7)0.0126 (7)0.0232 (8)
C13A0.0451 (9)0.0447 (9)0.0651 (11)0.0109 (7)0.0120 (8)0.0135 (8)
C14A0.0509 (10)0.0474 (10)0.0744 (13)0.0083 (8)0.0104 (9)0.0072 (9)
C15A0.0784 (16)0.0532 (13)0.121 (3)0.0005 (11)0.0194 (16)0.0108 (15)
C16A0.0789 (17)0.0607 (15)0.124 (3)0.0037 (13)0.0096 (16)0.0229 (17)
C17A0.107 (2)0.084 (2)0.095 (2)0.0037 (17)0.0019 (18)0.0254 (17)
C18A0.125 (3)0.119 (3)0.0500 (14)0.015 (2)0.0216 (16)0.0376 (16)
Cl1B0.0669 (3)0.0954 (4)0.0444 (3)0.0151 (3)0.0044 (2)0.0020 (2)
O1B0.1017 (11)0.0488 (7)0.0430 (7)0.0149 (7)0.0216 (7)0.0151 (6)
O2B0.1381 (16)0.0531 (9)0.0669 (10)0.0221 (9)0.0205 (10)0.0117 (7)
N1B0.0586 (9)0.0481 (8)0.0416 (8)0.0090 (6)0.0133 (6)0.0104 (6)
N2B0.0593 (9)0.0454 (8)0.0365 (7)0.0094 (6)0.0106 (6)0.0110 (6)
N3B0.0531 (8)0.0584 (9)0.0386 (7)0.0091 (7)0.0079 (6)0.0154 (6)
N4B0.0597 (9)0.0848 (12)0.0389 (8)0.0136 (8)0.0045 (7)0.0214 (8)
N5B0.0609 (10)0.0995 (14)0.0399 (8)0.0197 (9)0.0065 (7)0.0302 (9)
N6B0.0559 (9)0.0578 (9)0.0619 (10)0.0134 (7)0.0131 (7)0.0266 (8)
N7B0.0486 (7)0.0506 (8)0.0413 (7)0.0101 (6)0.0094 (6)0.0169 (6)
N8B0.0559 (8)0.0488 (8)0.0466 (8)0.0092 (6)0.0088 (6)0.0129 (6)
C1B0.0922 (18)0.0722 (16)0.0810 (17)0.0244 (13)0.0118 (14)0.0133 (14)
C2B0.0516 (10)0.0655 (12)0.0562 (11)0.0106 (9)0.0054 (8)0.0023 (9)
C3B0.0492 (9)0.0493 (10)0.0560 (10)0.0089 (7)0.0109 (8)0.0064 (8)
C4B0.0912 (16)0.0546 (12)0.0696 (14)0.0191 (11)0.0277 (12)0.0147 (11)
C5B0.133 (3)0.0565 (14)0.104 (2)0.0301 (15)0.0394 (19)0.0236 (15)
C6B0.132 (3)0.0558 (15)0.116 (3)0.0297 (16)0.024 (2)0.0018 (16)
C7B0.0493 (9)0.0460 (9)0.0401 (8)0.0072 (7)0.0089 (7)0.0114 (7)
C8B0.0424 (8)0.0507 (9)0.0413 (8)0.0069 (7)0.0066 (6)0.0150 (7)
C9B0.0424 (8)0.0705 (12)0.0411 (9)0.0089 (8)0.0053 (7)0.0209 (8)
C10B0.0574 (11)0.0866 (15)0.0531 (11)0.0195 (10)0.0106 (9)0.0346 (11)
C11B0.0456 (9)0.0702 (12)0.0477 (10)0.0125 (8)0.0085 (7)0.0288 (9)
C12B0.0434 (9)0.0601 (11)0.0528 (10)0.0107 (7)0.0092 (7)0.0273 (8)
C13B0.0516 (10)0.0491 (10)0.0570 (10)0.0085 (7)0.0088 (8)0.0202 (8)
C14B0.0624 (11)0.0489 (10)0.0655 (12)0.0086 (8)0.0109 (9)0.0174 (9)
C15B0.0911 (18)0.0568 (13)0.0921 (19)0.0220 (12)0.0008 (14)0.0206 (13)
C16B0.0935 (19)0.0510 (13)0.127 (3)0.0213 (12)0.0160 (16)0.0038 (15)
C17B0.134 (3)0.0572 (14)0.090 (2)0.0120 (15)0.0316 (18)0.0022 (14)
C18B0.092 (2)0.148 (3)0.0432 (12)0.049 (2)0.0150 (12)0.0417 (15)
O1W0.220 (4)0.1006 (19)0.176 (3)0.024 (2)0.090 (3)0.077 (2)
Geometric parameters (Å, º) top
Cl1A—C2A1.730 (2)O1B—C7B1.219 (2)
O1A—C7A1.213 (2)O2B—C14B1.355 (3)
O2A—C14A1.366 (3)O2B—C17B1.371 (3)
O2A—C17A1.376 (3)N1B—C7B1.351 (2)
N1A—C7A1.352 (2)N1B—C3B1.400 (2)
N1A—C3A1.403 (2)N1B—H80.87 (2)
N1A—H110.92 (2)N2B—C8B1.366 (2)
N2A—C8A1.365 (2)N2B—C7B1.399 (2)
N2A—C7A1.405 (2)N2B—H20.82 (2)
N2A—H10.85 (2)N3B—C8B1.296 (2)
N3A—C8A1.293 (2)N3B—C9B1.376 (2)
N3A—C9A1.382 (2)N4B—C9B1.336 (2)
N4A—C9A1.333 (2)N4B—N5B1.359 (2)
N4A—N5A1.366 (2)N5B—C10B1.331 (3)
N5A—C10A1.325 (3)N5B—C18B1.466 (3)
N5A—C18A1.461 (3)N6B—C12B1.317 (3)
N6A—C12A1.321 (2)N6B—C13B1.367 (2)
N6A—C13A1.364 (2)N7B—N8B1.373 (2)
N7A—C12A1.374 (2)N7B—C12B1.383 (2)
N7A—N8A1.375 (2)N7B—C8B1.388 (2)
N7A—C8A1.391 (2)N8B—C13B1.329 (2)
N8A—C13A1.329 (2)C1B—C6B1.369 (4)
C1A—C6A1.368 (4)C1B—C2B1.375 (3)
C1A—C2A1.383 (3)C1B—H170.97 (3)
C1A—H231.01 (2)C2B—C3B1.399 (3)
C2A—C3A1.400 (3)C3B—C4B1.387 (3)
C3A—C4A1.393 (3)C4B—C5B1.384 (3)
C4A—C5A1.387 (3)C4B—H60.86 (3)
C4A—H40.91 (2)C5B—C6B1.366 (4)
C5A—C6A1.380 (4)C5B—H140.90 (3)
C5A—H70.95 (3)C6B—H150.91 (4)
C6A—H120.94 (3)C9B—C11B1.405 (3)
C9A—C11A1.405 (3)C10B—C11B1.382 (3)
C10A—C11A1.385 (3)C10B—H131.01 (3)
C10A—H160.95 (3)C11B—C12B1.416 (3)
C11A—C12A1.411 (3)C13B—C14B1.449 (3)
C13A—C14A1.449 (3)C14B—C15B1.341 (3)
C14A—C15A1.346 (3)C15B—C16B1.407 (4)
C15A—C16A1.417 (5)C15B—H250.86 (3)
C15A—H210.91 (3)C16B—C17B1.313 (4)
C16A—C17A1.303 (5)C16B—H220.89 (3)
C16A—H180.97 (3)C17B—H200.97 (4)
C17A—H261.10 (4)C18B—H30.87 (3)
C18A—H90.90 (5)C18B—H51.07 (4)
C18A—H100.88 (4)C18B—H190.94 (4)
C18A—H240.96 (4)O1W—H2W0.90 (5)
Cl1B—C2B1.736 (2)O1W—H1W1.06 (5)
C14A—O2A—C17A105.9 (2)C7B—N1B—C3B126.76 (16)
C7A—N1A—C3A126.80 (15)C7B—N1B—H8114.5 (16)
C7A—N1A—H11114.9 (13)C3B—N1B—H8118.6 (16)
C3A—N1A—H11118.3 (13)C8B—N2B—C7B127.96 (15)
C8A—N2A—C7A128.89 (15)C8B—N2B—H2119.5 (14)
C8A—N2A—H1119.5 (14)C7B—N2B—H2112.5 (14)
C7A—N2A—H1111.4 (14)C8B—N3B—C9B116.89 (16)
C8A—N3A—C9A116.96 (15)C9B—N4B—N5B102.54 (17)
C9A—N4A—N5A102.68 (17)C10B—N5B—N4B114.69 (16)
C10A—N5A—N4A114.18 (17)C10B—N5B—C18B126.2 (2)
C10A—N5A—C18A126.7 (2)N4B—N5B—C18B119.2 (2)
N4A—N5A—C18A119.1 (2)C12B—N6B—C13B102.81 (15)
C12A—N6A—C13A103.06 (15)N8B—N7B—C12B109.94 (14)
C12A—N7A—N8A110.29 (14)N8B—N7B—C8B125.74 (14)
C12A—N7A—C8A124.32 (15)C12B—N7B—C8B124.32 (15)
N8A—N7A—C8A125.35 (14)C13B—N8B—N7B100.99 (14)
C13A—N8A—N7A100.92 (14)C6B—C1B—C2B119.8 (3)
C6A—C1A—C2A119.1 (2)C6B—C1B—H17120.9 (17)
C6A—C1A—H23122.3 (14)C2B—C1B—H17119.3 (17)
C2A—C1A—H23118.6 (14)C1B—C2B—C3B121.3 (2)
C1A—C2A—C3A121.7 (2)C1B—C2B—Cl1B119.06 (19)
C1A—C2A—Cl1A118.38 (17)C3B—C2B—Cl1B119.63 (16)
C3A—C2A—Cl1A119.87 (15)C4B—C3B—C2B117.89 (19)
C4A—C3A—C2A118.14 (17)C4B—C3B—N1B124.49 (18)
C4A—C3A—N1A124.36 (17)C2B—C3B—N1B117.62 (18)
C2A—C3A—N1A117.51 (17)C5B—C4B—C3B120.0 (2)
C5A—C4A—C3A119.7 (2)C5B—C4B—H6115.2 (19)
C5A—C4A—H4120.2 (14)C3B—C4B—H6124.8 (19)
C3A—C4A—H4120.1 (13)C6B—C5B—C4B121.1 (3)
C6A—C5A—C4A120.8 (3)C6B—C5B—H14124 (2)
C6A—C5A—H7123.6 (17)C4B—C5B—H14115 (2)
C4A—C5A—H7115.5 (17)C5B—C6B—C1B119.9 (3)
C1A—C6A—C5A120.5 (2)C5B—C6B—H15122 (2)
C1A—C6A—H12115.7 (18)C1B—C6B—H15118 (2)
C5A—C6A—H12123.7 (19)O1B—C7B—N1B125.08 (16)
O1A—C7A—N1A126.04 (16)O1B—C7B—N2B118.85 (16)
O1A—C7A—N2A118.72 (15)N1B—C7B—N2B116.06 (15)
N1A—C7A—N2A115.23 (15)N3B—C8B—N2B123.22 (16)
N3A—C8A—N2A123.90 (15)N3B—C8B—N7B121.52 (15)
N3A—C8A—N7A121.40 (15)N2B—C8B—N7B115.25 (15)
N2A—C8A—N7A114.70 (15)N4B—C9B—N3B122.73 (18)
N4A—C9A—N3A122.85 (17)N4B—C9B—C11B112.25 (16)
N4A—C9A—C11A112.49 (16)N3B—C9B—C11B125.03 (17)
N3A—C9A—C11A124.65 (16)N5B—C10B—C11B105.80 (19)
N5A—C10A—C11A106.4 (2)N5B—C10B—H13121.1 (15)
N5A—C10A—H16117.8 (15)C11B—C10B—H13133.0 (15)
C11A—C10A—H16135.9 (15)C10B—C11B—C9B104.71 (19)
C10A—C11A—C9A104.29 (19)C10B—C11B—C12B138.1 (2)
C10A—C11A—C12A138.5 (2)C9B—C11B—C12B117.22 (15)
C9A—C11A—C12A117.22 (16)N6B—C12B—N7B109.62 (16)
N6A—C12A—N7A109.34 (16)N6B—C12B—C11B135.35 (17)
N6A—C12A—C11A135.22 (17)N7B—C12B—C11B115.03 (16)
N7A—C12A—C11A115.43 (16)N8B—C13B—N6B116.63 (17)
N8A—C13A—N6A116.37 (17)N8B—C13B—C14B123.02 (17)
N8A—C13A—C14A122.73 (18)N6B—C13B—C14B120.29 (16)
N6A—C13A—C14A120.89 (17)C15B—C14B—O2B109.5 (2)
C15A—C14A—O2A109.7 (2)C15B—C14B—C13B131.4 (2)
C15A—C14A—C13A132.7 (2)O2B—C14B—C13B119.02 (17)
O2A—C14A—C13A117.64 (17)C14B—C15B—C16B106.7 (3)
C14A—C15A—C16A106.2 (3)C14B—C15B—H25121 (2)
C14A—C15A—H21122 (2)C16B—C15B—H25132 (2)
C16A—C15A—H21131 (2)C17B—C16B—C15B107.3 (2)
C17A—C16A—C15A107.7 (3)C17B—C16B—H22124 (2)
C17A—C16A—H18121.4 (18)C15B—C16B—H22129 (2)
C15A—C16A—H18130.9 (18)C16B—C17B—O2B110.0 (3)
C16A—C17A—O2A110.5 (3)C16B—C17B—H20136 (2)
C16A—C17A—H26139 (2)O2B—C17B—H20114 (2)
O2A—C17A—H26110 (2)N5B—C18B—H3106 (2)
N5A—C18A—H9110 (3)N5B—C18B—H5108 (2)
N5A—C18A—H10109 (3)H3—C18B—H5116 (3)
H9—C18A—H10114 (4)N5B—C18B—H19110 (2)
N5A—C18A—H24109 (2)H3—C18B—H19114 (3)
H9—C18A—H24106 (3)H5—C18B—H19103 (3)
H10—C18A—H24108 (3)H2W—O1W—H1W89 (4)
C14B—O2B—C17B106.4 (2)
(compound2) N-[8-butyl-2-(2-furyl)-8H-pyrazolo[4,3-e][1,2,4]triazolo [1,5-c]pyrimidin-5-yl] N-(3-methoxyphenyl)-urea top
Crystal data top
C22H22N8O3F(000) = 936
Mr = 446.48Dx = 1.377 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.2816 (2) ÅCell parameters from 9542 reflections
b = 24.0888 (5) Åθ = 2.7–28.0°
c = 8.1651 (3) ŵ = 0.10 mm1
β = 103.9170 (8)°T = 295 K
V = 2153.81 (10) Å3Plate, colourless
Z = 40.51 × 0.19 × 0.07 mm
Data collection top
Nonius Kappa CCD
diffractometer
2594 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.057
Graphite monochromatorθmax = 28.0°, θmin = 2.7°
ϕ scans and ω scansh = 1414
9542 measured reflectionsk = 3031
5159 independent reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: difference Fourier map
wR(F2) = 0.141All H-atom parameters refined
S = 1.02 w = 1/[σ2(Fo2) + (0.0509P)2 + 0.3032P]
where P = (Fo2 + 2Fc2)/3
5159 reflections(Δ/σ)max = 0.001
396 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C22H22N8O3V = 2153.81 (10) Å3
Mr = 446.48Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.2816 (2) ŵ = 0.10 mm1
b = 24.0888 (5) ÅT = 295 K
c = 8.1651 (3) Å0.51 × 0.19 × 0.07 mm
β = 103.9170 (8)°
Data collection top
Nonius Kappa CCD
diffractometer
2594 reflections with I > 2σ(I)
9542 measured reflectionsRint = 0.057
5159 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.141All H-atom parameters refined
S = 1.02Δρmax = 0.19 e Å3
5159 reflectionsΔρmin = 0.24 e Å3
396 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.03830 (15)0.05812 (7)0.7801 (2)0.0621 (5)
O20.49327 (17)0.05909 (7)1.0177 (2)0.0737 (6)
O30.25764 (15)0.14966 (7)0.5524 (2)0.0673 (5)
N10.07798 (17)0.01383 (9)0.7218 (2)0.0505 (5)
N20.09438 (18)0.02939 (8)0.8222 (2)0.0505 (5)
N30.00331 (16)0.11552 (7)0.7922 (2)0.0451 (5)
N40.06447 (16)0.20783 (8)0.7643 (2)0.0459 (5)
N50.01815 (16)0.25837 (7)0.7913 (2)0.0448 (5)
N60.30006 (16)0.17494 (8)0.9565 (2)0.0464 (5)
N70.27852 (16)0.08103 (8)0.9248 (2)0.0462 (5)
N80.18402 (16)0.11008 (7)0.8847 (2)0.0426 (4)
C10.2653 (2)0.09355 (9)0.5745 (3)0.0482 (6)
C20.1711 (2)0.06997 (10)0.6339 (3)0.0486 (6)
C30.16903 (19)0.01402 (9)0.6605 (3)0.0440 (5)
C40.2591 (3)0.01922 (12)0.6253 (4)0.0749 (9)
C50.3534 (12)0.0044 (3)0.578 (4)0.102 (3)0.84 (6)
C5A0.342 (2)0.0062 (15)0.520 (3)0.030 (11)0.16 (6)
C60.3551 (3)0.06115 (12)0.5399 (4)0.0732 (8)
C70.0158 (2)0.00908 (10)0.7718 (3)0.0465 (5)
C80.08811 (19)0.08572 (9)0.8309 (3)0.0423 (5)
C90.01466 (19)0.17222 (9)0.8051 (2)0.0403 (5)
C100.0839 (2)0.25557 (10)0.8476 (3)0.0458 (5)
C110.10892 (18)0.19987 (9)0.8592 (2)0.0406 (5)
C120.19919 (19)0.16606 (9)0.9041 (3)0.0413 (5)
C130.3437 (2)0.12249 (9)0.9663 (3)0.0443 (5)
C140.4572 (2)0.11279 (10)1.0154 (3)0.0496 (6)
C150.5400 (2)0.14631 (13)1.0563 (3)0.0624 (7)
C160.6341 (3)0.11167 (15)1.0853 (4)0.0787 (9)
C170.6028 (3)0.06001 (17)1.0608 (4)0.0890 (10)
C180.3587 (3)0.17815 (14)0.5140 (5)0.0661 (8)
C190.0816 (2)0.30892 (10)0.7589 (3)0.0490 (6)
C200.1728 (2)0.33018 (10)0.9123 (3)0.0505 (6)
C210.2812 (3)0.29260 (13)0.9779 (4)0.0635 (7)
C220.3661 (3)0.31516 (19)1.1360 (5)0.0816 (9)
H10.2045 (18)0.3673 (9)0.888 (2)0.047 (6)*
H20.1304 (19)0.3367 (9)1.004 (3)0.054 (6)*
H30.1276 (19)0.2884 (10)0.873 (2)0.054 (6)*
H40.255 (3)0.0567 (12)0.645 (3)0.084 (9)*
H50.410 (3)0.0174 (14)0.539 (4)0.108 (11)*
H60.375 (3)0.1645 (12)0.407 (4)0.097 (10)*
H70.417 (2)0.0785 (11)0.496 (3)0.081 (8)*
H80.110 (2)0.0931 (10)0.654 (3)0.058 (7)*
H90.396 (3)0.3537 (15)1.114 (4)0.102 (11)*
H100.433 (3)0.1706 (11)0.604 (4)0.088 (10)*
H110.162 (2)0.0128 (10)0.843 (3)0.068 (8)*
H120.014 (2)0.3381 (11)0.720 (3)0.068 (7)*
H130.337 (3)0.2191 (15)0.511 (4)0.116 (12)*
H140.322 (2)0.2876 (11)0.889 (3)0.076 (8)*
H150.080 (2)0.0508 (12)0.720 (3)0.082 (9)*
H160.315 (3)0.3211 (13)1.218 (4)0.115 (12)*
H170.254 (2)0.2546 (12)1.001 (3)0.077 (8)*
H180.536 (2)0.1835 (10)1.060 (3)0.055 (7)*
H190.122 (2)0.2982 (9)0.669 (3)0.055 (6)*
H200.702 (3)0.1207 (12)1.112 (4)0.091 (10)*
H210.644 (3)0.0221 (15)1.066 (4)0.123 (12)*
H220.436 (3)0.2914 (14)1.171 (4)0.105 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0685 (11)0.0303 (10)0.0978 (13)0.0033 (8)0.0402 (10)0.0052 (8)
O20.0693 (11)0.0506 (12)0.1187 (15)0.0103 (9)0.0570 (11)0.0127 (10)
O30.0671 (11)0.0392 (11)0.1095 (14)0.0025 (9)0.0482 (10)0.0109 (9)
N10.0517 (12)0.0297 (12)0.0769 (13)0.0011 (10)0.0291 (10)0.0019 (10)
N20.0516 (12)0.0306 (12)0.0768 (14)0.0038 (10)0.0301 (11)0.0054 (9)
N30.0489 (11)0.0323 (11)0.0585 (12)0.0011 (9)0.0214 (9)0.0043 (8)
N40.0531 (11)0.0316 (11)0.0572 (11)0.0018 (9)0.0210 (9)0.0033 (9)
N50.0531 (11)0.0329 (11)0.0513 (11)0.0013 (9)0.0182 (9)0.0012 (8)
N60.0498 (11)0.0364 (12)0.0576 (12)0.0011 (9)0.0219 (9)0.0016 (9)
N70.0489 (11)0.0376 (11)0.0569 (11)0.0033 (9)0.0222 (9)0.0001 (9)
N80.0436 (10)0.0323 (11)0.0555 (11)0.0004 (9)0.0188 (9)0.0010 (8)
C10.0527 (14)0.0346 (14)0.0607 (14)0.0009 (11)0.0202 (11)0.0003 (11)
C20.0535 (15)0.0353 (15)0.0634 (15)0.0008 (12)0.0267 (12)0.0004 (11)
C30.0447 (13)0.0343 (14)0.0554 (13)0.0012 (11)0.0168 (10)0.0034 (10)
C40.0732 (19)0.0337 (17)0.134 (3)0.0023 (14)0.0558 (19)0.0039 (16)
C50.107 (5)0.049 (3)0.183 (11)0.017 (4)0.099 (5)0.009 (5)
C5A0.016 (15)0.051 (14)0.025 (19)0.014 (9)0.009 (12)0.007 (7)
C60.0665 (18)0.0479 (18)0.121 (2)0.0033 (15)0.0531 (18)0.0012 (16)
C70.0504 (14)0.0312 (14)0.0606 (14)0.0006 (11)0.0190 (11)0.0040 (10)
C80.0435 (13)0.0317 (13)0.0554 (13)0.0004 (11)0.0191 (10)0.0037 (10)
C90.0483 (13)0.0283 (12)0.0460 (12)0.0005 (10)0.0146 (10)0.0028 (9)
C100.0489 (13)0.0372 (15)0.0545 (13)0.0013 (11)0.0186 (11)0.0039 (11)
C110.0438 (12)0.0324 (13)0.0478 (12)0.0004 (10)0.0154 (10)0.0032 (9)
C120.0460 (13)0.0305 (13)0.0486 (12)0.0021 (10)0.0141 (10)0.0027 (9)
C130.0480 (13)0.0398 (14)0.0480 (12)0.0020 (11)0.0172 (10)0.0021 (10)
C140.0540 (14)0.0408 (14)0.0596 (14)0.0021 (12)0.0246 (12)0.0034 (11)
C150.0670 (18)0.0568 (19)0.0710 (17)0.0090 (16)0.0313 (14)0.0027 (15)
C160.0598 (18)0.091 (3)0.101 (2)0.0026 (18)0.0490 (17)0.0084 (18)
C170.078 (2)0.074 (2)0.136 (3)0.0144 (19)0.068 (2)0.018 (2)
C180.0652 (19)0.053 (2)0.085 (2)0.0109 (16)0.0283 (18)0.0111 (16)
C190.0625 (16)0.0332 (14)0.0560 (15)0.0047 (12)0.0235 (13)0.0022 (11)
C200.0640 (16)0.0357 (15)0.0581 (15)0.0077 (12)0.0272 (13)0.0036 (11)
C210.0666 (18)0.0519 (19)0.0737 (18)0.0058 (15)0.0200 (15)0.0030 (15)
C220.061 (2)0.091 (3)0.089 (2)0.010 (2)0.0107 (18)0.006 (2)
Geometric parameters (Å, º) top
O1—C71.214 (2)C5—C61.402 (12)
O2—C141.358 (3)C5—H50.94 (3)
O2—C171.364 (3)C5A—C61.34 (4)
O3—C11.364 (3)C5A—H50.94 (5)
O3—C181.428 (3)C6—H70.95 (3)
N1—C71.341 (3)C9—C111.413 (3)
N1—C31.416 (3)C10—C111.379 (3)
N1—H150.89 (3)C10—H30.98 (2)
N2—C81.360 (3)C11—C121.419 (3)
N2—C71.411 (3)C13—C141.450 (3)
N2—H110.91 (2)C14—C151.337 (3)
N3—C81.295 (3)C15—C161.414 (4)
N3—C91.378 (3)C15—H180.90 (2)
N4—C91.336 (3)C16—C171.322 (4)
N4—N51.364 (2)C16—H200.87 (3)
N5—C101.340 (3)C17—H211.03 (3)
N5—C191.469 (3)C18—H61.00 (3)
N6—C121.326 (3)C18—H100.99 (3)
N6—C131.365 (3)C18—H131.01 (4)
N7—C131.331 (3)C19—C201.506 (3)
N7—N81.379 (2)C19—H121.03 (3)
N8—C121.373 (2)C19—H190.99 (2)
N8—C81.392 (2)C20—C211.513 (4)
C1—C61.362 (3)C20—H11.00 (2)
C1—C21.391 (3)C20—H20.99 (2)
C2—C31.366 (3)C21—C221.512 (4)
C2—H80.93 (2)C21—H140.95 (3)
C3—C41.377 (3)C21—H171.00 (3)
C4—C51.344 (10)C22—H91.02 (3)
C4—C5A1.54 (3)C22—H161.00 (3)
C4—H40.92 (3)C22—H220.96 (3)
C14—O2—C17106.3 (2)N5—C10—C11106.22 (19)
C1—O3—C18118.5 (2)N5—C10—H3123.3 (13)
C7—N1—C3127.3 (2)C11—C10—H3130.5 (13)
C7—N1—H15115.9 (17)C10—C11—C9104.80 (18)
C3—N1—H15116.6 (17)C10—C11—C12138.4 (2)
C8—N2—C7129.97 (19)C9—C11—C12116.80 (19)
C8—N2—H11117.6 (16)N6—C12—N8109.63 (18)
C7—N2—H11112.2 (16)N6—C12—C11135.7 (2)
C8—N3—C9116.30 (17)N8—C12—C11114.64 (18)
C9—N4—N5103.19 (16)N7—C13—N6116.77 (19)
C10—N5—N4113.87 (18)N7—C13—C14121.9 (2)
C10—N5—C19126.9 (2)N6—C13—C14121.34 (19)
N4—N5—C19119.27 (18)C15—C14—O2110.0 (2)
C12—N6—C13102.65 (17)C15—C14—C13133.5 (2)
C13—N7—N8100.69 (17)O2—C14—C13116.42 (19)
C12—N8—N7110.25 (16)C14—C15—C16106.5 (3)
C12—N8—C8125.33 (18)C14—C15—H18125.0 (15)
N7—N8—C8124.41 (18)C16—C15—H18128.4 (15)
C6—C1—O3124.5 (2)C17—C16—C15106.9 (3)
C6—C1—C2120.5 (2)C17—C16—H20123.7 (19)
O3—C1—C2115.0 (2)C15—C16—H20129.4 (19)
C3—C2—C1120.1 (2)C16—C17—O2110.2 (3)
C3—C2—H8121.5 (14)C16—C17—H21133.5 (19)
C1—C2—H8118.4 (14)O2—C17—H21116.3 (19)
C2—C3—C4119.9 (2)O3—C18—H6111.3 (17)
C2—C3—N1124.4 (2)O3—C18—H10109.2 (16)
C4—C3—N1115.7 (2)H6—C18—H10107 (2)
C5—C4—C3119.3 (4)O3—C18—H13105.9 (18)
C5—C4—C5A16.7 (14)H6—C18—H13113 (2)
C3—C4—C5A117.5 (14)H10—C18—H13111 (3)
C5—C4—H4122.8 (18)N5—C19—C20113.38 (19)
C3—C4—H4117.7 (17)N5—C19—H12105.3 (13)
C5A—C4—H4123 (2)C20—C19—H12109.3 (13)
C4—C5—C6122.0 (6)N5—C19—H19104.4 (13)
C4—C5—H5121 (2)C20—C19—H19111.2 (13)
C6—C5—H5115 (3)H12—C19—H19113.1 (18)
C6—C5A—C4113 (2)C19—C20—C21115.1 (2)
C6—C5A—H5121 (3)C19—C20—H1110.0 (12)
C4—C5A—H5105 (3)C21—C20—H1107.9 (12)
C5A—C6—C1121.5 (11)C19—C20—H2109.0 (12)
C5A—C6—C519.2 (12)C21—C20—H2108.8 (12)
C1—C6—C5117.5 (5)H1—C20—H2105.7 (17)
C5A—C6—H7117 (2)C22—C21—C20112.3 (3)
C1—C6—H7118.4 (17)C22—C21—H14111.9 (16)
C5—C6—H7124.1 (17)C20—C21—H14107.6 (16)
O1—C7—N1127.5 (2)C22—C21—H17109.4 (15)
O1—C7—N2117.9 (2)C20—C21—H17110.6 (15)
N1—C7—N2114.6 (2)H14—C21—H17105 (2)
N3—C8—N2124.94 (19)C21—C22—H9110.1 (17)
N3—C8—N8121.3 (2)C21—C22—H16106.1 (19)
N2—C8—N8113.75 (18)H9—C22—H16105 (3)
N4—C9—N3122.49 (18)C21—C22—H22110.2 (19)
N4—C9—C11111.91 (19)H9—C22—H22108 (3)
N3—C9—C11125.59 (19)H16—C22—H22117 (3)
(compound3) N-[8-butyl-2-(2-furyl)-8H-pyrazolo[4,3-e][1,2,4] triazolo[1,5-c]pyrimidin-5-yl]N-(2-methoxyphenyl)urea 0.5 dioxane solvate top
Crystal data top
(C22H22N8O3)·0.5(C4H8O2)Z = 4
Mr = 490.53F(000) = 1032
Triclinic, P1Dx = 1.336 Mg m3
a = 12.6218 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.0932 (3) ÅCell parameters from 15610 reflections
c = 15.6948 (4) Åθ = 2.0–27.0°
α = 72.8670 (7)°µ = 0.10 mm1
β = 71.3280 (7)°T = 295 K
γ = 70.6350 (9)°Prism, colourless
V = 2439.16 (9) Å30.33 × 0.24 × 0.19 mm
Data collection top
Nonius Kappa CCD
diffractometer
6467 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 27.0°, θmin = 2.0°
ϕ scans and ω scansh = 1316
15610 measured reflectionsk = 1717
10558 independent reflectionsl = 1920
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.183 w = 1/[σ2(Fo2) + (0.0836P)2 + 0.5314P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
10558 reflectionsΔρmax = 0.27 e Å3
889 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.054 (5)
Crystal data top
(C22H22N8O3)·0.5(C4H8O2)γ = 70.6350 (9)°
Mr = 490.53V = 2439.16 (9) Å3
Triclinic, P1Z = 4
a = 12.6218 (2) ÅMo Kα radiation
b = 14.0932 (3) ŵ = 0.10 mm1
c = 15.6948 (4) ÅT = 295 K
α = 72.8670 (7)°0.33 × 0.24 × 0.19 mm
β = 71.3280 (7)°
Data collection top
Nonius Kappa CCD
diffractometer
6467 reflections with I > 2σ(I)
15610 measured reflectionsRint = 0.024
10558 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.183H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.27 e Å3
10558 reflectionsΔρmin = 0.20 e Å3
889 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A1.28893 (15)0.26617 (15)0.09746 (13)0.0801 (5)
O2A0.83391 (15)0.15403 (14)0.24399 (11)0.0783 (5)
O3A1.29417 (16)0.18973 (14)0.37575 (11)0.0766 (5)
N1A1.27861 (17)0.20955 (15)0.21577 (13)0.0633 (5)
N2A1.13523 (17)0.20846 (16)0.08019 (14)0.0652 (5)
N3A1.07998 (16)0.15832 (14)0.18595 (12)0.0595 (5)
N4A1.00524 (17)0.10412 (14)0.28009 (13)0.0649 (5)
N5A0.91157 (18)0.06644 (15)0.26095 (13)0.0659 (5)
N6A0.81605 (16)0.09127 (15)0.03984 (12)0.0637 (5)
N7A0.96959 (15)0.15020 (13)0.03305 (12)0.0563 (4)
N8A0.94590 (15)0.16261 (14)0.05526 (12)0.0603 (5)
C1A1.4751 (2)0.2423 (2)0.44474 (19)0.0768 (7)
C2A1.3835 (2)0.22130 (17)0.37188 (16)0.0633 (6)
C3A1.37741 (18)0.23070 (17)0.28404 (15)0.0592 (5)
C4A1.4644 (2)0.2586 (2)0.27045 (19)0.0694 (6)
C5A1.5568 (2)0.2793 (2)0.3441 (2)0.0797 (7)
C6A1.5616 (2)0.2712 (2)0.4298 (2)0.0828 (8)
C7A1.24083 (19)0.23127 (17)0.13209 (16)0.0601 (5)
C8A1.06366 (18)0.17239 (16)0.10458 (15)0.0560 (5)
C9A1.00097 (19)0.11965 (16)0.19892 (15)0.0570 (5)
C10A0.8514 (2)0.05770 (19)0.17312 (16)0.0669 (6)
C11A0.9056 (2)0.09250 (17)0.12981 (15)0.0588 (5)
C12A0.89075 (18)0.10777 (16)0.04093 (15)0.0566 (5)
C13A0.85326 (19)0.12591 (17)0.09490 (15)0.0588 (5)
C14A0.7926 (2)0.12113 (19)0.19094 (15)0.0646 (6)
C15A0.6993 (3)0.0874 (2)0.24127 (19)0.0844 (8)
C16A0.6803 (3)0.1005 (3)0.3317 (2)0.0943 (9)
C17A0.7622 (3)0.1399 (3)0.33005 (19)0.0890 (9)
C18A1.2889 (4)0.1795 (3)0.4606 (2)0.0944 (9)
C19A0.8914 (3)0.0366 (2)0.33535 (19)0.0781 (7)
C20A0.7725 (3)0.0201 (2)0.3120 (2)0.0757 (7)
C21A0.7471 (3)0.0041 (3)0.3900 (3)0.0960 (10)
C22A0.6300 (4)0.0260 (4)0.3629 (4)0.1158 (14)
O1B0.85787 (15)0.24873 (14)0.55214 (11)0.0771 (5)
O2B0.57986 (15)0.31651 (15)0.12631 (12)0.0829 (5)
O3B1.21344 (15)0.35088 (18)0.66246 (13)0.0947 (6)
N1B1.01712 (16)0.30987 (15)0.58938 (13)0.0605 (5)
N2B0.88489 (16)0.31312 (15)0.44787 (13)0.0599 (5)
N3B1.03549 (15)0.37727 (14)0.45036 (12)0.0574 (4)
N4B1.17808 (15)0.44127 (14)0.43220 (13)0.0601 (5)
N5B1.18979 (15)0.46648 (14)0.35848 (13)0.0591 (5)
N6B0.85096 (15)0.38809 (14)0.18119 (12)0.0604 (5)
N7B0.88282 (14)0.36002 (13)0.31875 (11)0.0528 (4)
N8B0.77962 (14)0.33578 (14)0.27164 (12)0.0571 (4)
C1B1.2444 (3)0.2883 (3)0.8021 (2)0.0897 (9)
C2B1.1810 (2)0.3098 (2)0.71638 (16)0.0704 (6)
C3B1.07312 (18)0.28892 (17)0.67781 (14)0.0585 (5)
C4B1.0305 (2)0.25047 (19)0.72733 (16)0.0656 (6)
C5B1.0945 (3)0.2300 (2)0.81245 (18)0.0801 (7)
C6B1.2014 (3)0.2480 (3)0.8489 (2)0.0918 (9)
C7B0.91880 (18)0.28774 (17)0.53427 (14)0.0573 (5)
C8B0.93964 (17)0.35111 (15)0.40910 (14)0.0525 (5)
C9B1.07977 (17)0.41167 (16)0.39875 (15)0.0545 (5)
C10B1.10419 (19)0.45399 (17)0.28249 (17)0.0604 (6)
C11B1.03001 (18)0.41875 (16)0.30628 (15)0.0556 (5)
C12B0.92377 (18)0.39100 (16)0.26342 (14)0.0541 (5)
C13B0.76576 (18)0.35480 (17)0.19028 (15)0.0567 (5)
C14B0.6663 (2)0.3447 (2)0.11459 (16)0.0663 (6)
C15B0.6222 (14)0.3839 (12)0.0354 (14)0.086 (4)0.50
C15C0.6528 (13)0.3418 (11)0.0266 (13)0.076 (3)0.50
C16B0.5166 (17)0.3651 (11)0.0087 (13)0.095 (4)0.50
C16C0.5422 (18)0.3172 (11)0.0183 (16)0.103 (5)0.50
C17B0.485 (3)0.331 (3)0.044 (3)0.091 (6)0.50
C17C0.509 (2)0.304 (3)0.047 (3)0.093 (7)0.50
C18B1.3233 (3)0.3724 (4)0.6945 (3)0.1020 (11)
C19B1.2914 (2)0.5024 (2)0.37002 (18)0.0659 (6)
C20B1.2907 (2)0.5286 (2)0.2837 (2)0.0694 (6)
C21B1.3957 (3)0.5645 (3)0.2930 (2)0.0898 (9)
C22B1.3902 (4)0.5925 (4)0.2052 (3)0.1091 (12)
O501.3901 (6)0.0278 (5)0.0551 (5)0.106 (2)0.50
O50A1.4158 (7)0.0344 (7)0.0750 (5)0.132 (3)0.50
C501.5102 (4)0.0104 (4)0.0876 (3)0.1274 (14)
C511.4092 (4)0.0192 (5)0.0135 (4)0.161 (2)
O601.0547 (4)0.4064 (3)0.0231 (4)0.1021 (17)0.60
O60A1.0613 (12)0.4510 (11)0.0734 (6)0.163 (5)0.40
C60A0.9371 (7)0.4840 (10)0.0501 (7)0.101 (3)0.40
C600.9325 (6)0.4312 (5)0.0293 (8)0.109 (2)0.60
C610.860 (3)0.515 (3)0.043 (2)0.203 (17)0.30
C61A0.8868 (5)0.5329 (6)0.0057 (8)0.121 (3)0.70
H10.820 (2)0.2994 (16)0.4108 (16)0.059 (6)*
H21.248 (3)0.230 (2)0.908 (2)0.099 (9)*
H30.634 (4)0.107 (3)0.308 (3)0.163 (16)*
H41.364 (2)0.4472 (18)0.3905 (17)0.073 (7)*
H51.319 (2)0.406 (2)0.649 (2)0.082 (9)*
H60.782 (3)0.162 (2)0.371 (2)0.104 (10)*
H71.109 (2)0.2257 (17)0.0288 (18)0.067 (7)*
H81.283 (3)0.244 (2)0.506 (2)0.114 (12)*
H91.103 (2)0.4677 (18)0.2259 (19)0.077 (7)*
H100.952 (3)0.029 (2)0.351 (2)0.095 (9)*
H111.222 (2)0.583 (2)0.2691 (18)0.080 (8)*
H121.313 (3)0.298 (2)0.816 (2)0.093 (9)*
H130.957 (2)0.2395 (18)0.7034 (19)0.080 (8)*
H141.478 (2)0.2307 (19)0.505 (2)0.086 (8)*
H150.903 (3)0.093 (2)0.391 (2)0.111 (10)*
H160.782 (2)0.0322 (18)0.1499 (17)0.074 (7)*
H181.403 (3)0.617 (3)0.347 (2)0.113 (11)*
H191.363 (3)0.125 (2)0.487 (2)0.112 (10)*
H201.047 (2)0.3401 (17)0.5662 (16)0.064 (7)*
H211.288 (2)0.469 (2)0.2359 (18)0.075 (7)*
H220.483 (4)0.352 (3)0.070 (3)0.154 (15)*
H231.619 (3)0.304 (2)0.330 (2)0.104 (9)*
H251.220 (3)0.153 (2)0.448 (2)0.100 (10)*
H261.627 (3)0.288 (2)0.481 (2)0.107 (9)*
H270.818 (3)0.066 (3)0.415 (2)0.124 (11)*
H280.619 (3)0.081 (2)0.387 (2)0.123 (11)*
H290.656 (3)0.063 (2)0.217 (2)0.105 (10)*
H301.2883 (19)0.5632 (18)0.4229 (17)0.069 (7)*
H310.716 (2)0.079 (2)0.2944 (19)0.086 (8)*
H320.678 (3)0.382 (3)0.008 (3)0.134 (14)*
H340.763 (2)0.043 (2)0.255 (2)0.091 (8)*
H351.231 (2)0.1896 (18)0.2318 (17)0.068 (7)*
H361.303 (4)0.646 (3)0.178 (3)0.169 (16)*
H371.064 (3)0.198 (2)0.844 (2)0.102 (10)*
H380.435 (3)0.297 (3)0.049 (2)0.120 (13)*
H390.610 (4)0.042 (3)0.409 (3)0.148 (14)*
H401.388 (3)0.295 (3)0.702 (2)0.119 (11)*
H411.448 (4)0.626 (3)0.215 (3)0.156 (15)*
H421.472 (4)0.505 (3)0.319 (3)0.150 (14)*
H431.328 (3)0.419 (2)0.750 (2)0.108 (11)*
H440.573 (3)0.023 (3)0.336 (3)0.122 (13)*
H451.400 (3)0.529 (3)0.158 (3)0.143 (16)*
H480.757 (3)0.046 (3)0.439 (3)0.132 (15)*
H511.463 (2)0.2659 (19)0.210 (2)0.087 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0636 (10)0.1176 (14)0.0770 (11)0.0392 (9)0.0016 (8)0.0463 (10)
O2A0.0799 (11)0.1139 (13)0.0529 (9)0.0472 (10)0.0024 (8)0.0249 (9)
O3A0.0827 (12)0.0999 (12)0.0569 (10)0.0395 (9)0.0071 (8)0.0242 (8)
N1A0.0574 (11)0.0837 (13)0.0536 (11)0.0328 (10)0.0011 (9)0.0190 (9)
N2A0.0599 (11)0.0922 (14)0.0525 (11)0.0349 (10)0.0034 (9)0.0301 (10)
N3A0.0613 (11)0.0681 (11)0.0519 (11)0.0277 (9)0.0025 (8)0.0173 (8)
N4A0.0751 (13)0.0694 (11)0.0547 (11)0.0302 (9)0.0060 (9)0.0175 (9)
N5A0.0810 (13)0.0721 (12)0.0532 (11)0.0327 (10)0.0117 (9)0.0166 (9)
N6A0.0645 (11)0.0817 (12)0.0508 (10)0.0348 (9)0.0030 (9)0.0169 (9)
N7A0.0559 (10)0.0696 (11)0.0471 (10)0.0260 (8)0.0038 (8)0.0169 (8)
N8A0.0591 (11)0.0771 (12)0.0475 (10)0.0270 (9)0.0017 (8)0.0194 (8)
C1A0.0737 (17)0.0878 (17)0.0579 (15)0.0252 (13)0.0028 (12)0.0157 (13)
C2A0.0580 (13)0.0683 (13)0.0585 (14)0.0197 (10)0.0040 (10)0.0139 (10)
C3A0.0508 (12)0.0671 (13)0.0541 (13)0.0187 (10)0.0020 (9)0.0128 (10)
C4A0.0560 (14)0.0880 (17)0.0649 (16)0.0261 (12)0.0074 (11)0.0171 (13)
C5A0.0549 (14)0.0969 (19)0.0811 (19)0.0279 (13)0.0017 (13)0.0171 (14)
C6A0.0579 (15)0.0975 (19)0.0767 (19)0.0273 (13)0.0074 (13)0.0129 (14)
C7A0.0529 (12)0.0699 (13)0.0582 (13)0.0206 (10)0.0028 (10)0.0212 (11)
C8A0.0537 (12)0.0618 (12)0.0520 (12)0.0219 (9)0.0013 (9)0.0166 (9)
C9A0.0621 (13)0.0583 (12)0.0516 (12)0.0209 (10)0.0066 (10)0.0151 (9)
C10A0.0769 (16)0.0784 (15)0.0536 (13)0.0360 (13)0.0088 (12)0.0160 (11)
C11A0.0643 (13)0.0661 (13)0.0506 (12)0.0286 (10)0.0064 (10)0.0143 (10)
C12A0.0565 (12)0.0634 (12)0.0533 (12)0.0260 (10)0.0064 (10)0.0133 (9)
C13A0.0587 (13)0.0697 (13)0.0510 (12)0.0255 (10)0.0068 (10)0.0146 (10)
C14A0.0633 (14)0.0845 (15)0.0515 (13)0.0325 (12)0.0033 (10)0.0193 (11)
C15A0.0842 (19)0.115 (2)0.0645 (16)0.0549 (17)0.0062 (14)0.0291 (15)
C16A0.101 (2)0.125 (2)0.0589 (16)0.0586 (19)0.0124 (15)0.0254 (15)
C17A0.099 (2)0.125 (2)0.0508 (15)0.0506 (19)0.0020 (14)0.0289 (15)
C18A0.100 (2)0.123 (3)0.074 (2)0.030 (2)0.0173 (18)0.043 (2)
C19A0.109 (2)0.0799 (18)0.0597 (15)0.0383 (16)0.0186 (15)0.0219 (14)
C20A0.0894 (19)0.0740 (16)0.0759 (18)0.0179 (14)0.0328 (15)0.0237 (14)
C21A0.120 (3)0.098 (2)0.089 (2)0.018 (2)0.044 (2)0.039 (2)
C22A0.119 (3)0.126 (3)0.143 (4)0.017 (2)0.066 (3)0.067 (3)
O1B0.0685 (10)0.1187 (13)0.0632 (10)0.0503 (10)0.0013 (8)0.0339 (9)
O2B0.0667 (11)0.1342 (15)0.0636 (11)0.0537 (10)0.0023 (9)0.0327 (10)
O3B0.0652 (11)0.1592 (18)0.0675 (11)0.0609 (12)0.0012 (9)0.0159 (11)
N1B0.0531 (11)0.0847 (13)0.0494 (10)0.0301 (9)0.0034 (8)0.0187 (9)
N2B0.0503 (10)0.0886 (13)0.0491 (10)0.0339 (9)0.0010 (8)0.0211 (9)
N3B0.0500 (10)0.0751 (11)0.0513 (10)0.0266 (8)0.0052 (8)0.0157 (8)
N4B0.0504 (10)0.0743 (11)0.0596 (11)0.0260 (8)0.0092 (8)0.0139 (9)
N5B0.0498 (10)0.0704 (11)0.0631 (11)0.0255 (8)0.0116 (8)0.0140 (9)
N6B0.0554 (10)0.0809 (12)0.0511 (10)0.0296 (9)0.0057 (8)0.0178 (9)
N7B0.0457 (9)0.0695 (10)0.0475 (9)0.0254 (8)0.0036 (7)0.0157 (8)
N8B0.0485 (10)0.0757 (11)0.0506 (10)0.0280 (8)0.0016 (8)0.0167 (8)
C1B0.0616 (17)0.125 (2)0.0634 (17)0.0294 (16)0.0067 (13)0.0112 (16)
C2B0.0589 (14)0.0985 (17)0.0509 (13)0.0278 (12)0.0094 (11)0.0076 (12)
C3B0.0525 (12)0.0708 (13)0.0442 (11)0.0167 (10)0.0041 (9)0.0087 (10)
C4B0.0663 (15)0.0773 (15)0.0510 (13)0.0208 (12)0.0075 (11)0.0160 (11)
C5B0.095 (2)0.0883 (18)0.0524 (14)0.0255 (15)0.0071 (14)0.0187 (13)
C6B0.094 (2)0.114 (2)0.0533 (16)0.0215 (17)0.0019 (15)0.0248 (15)
C7B0.0505 (12)0.0763 (13)0.0483 (12)0.0254 (10)0.0048 (9)0.0160 (10)
C8B0.0478 (11)0.0645 (12)0.0466 (11)0.0192 (9)0.0064 (9)0.0146 (9)
C9B0.0462 (11)0.0614 (12)0.0557 (12)0.0198 (9)0.0067 (9)0.0119 (9)
C10B0.0544 (13)0.0740 (14)0.0590 (14)0.0263 (10)0.0107 (11)0.0158 (11)
C11B0.0503 (12)0.0668 (12)0.0542 (12)0.0236 (9)0.0086 (9)0.0145 (10)
C12B0.0502 (11)0.0656 (12)0.0500 (12)0.0222 (9)0.0089 (9)0.0134 (9)
C13B0.0517 (12)0.0735 (13)0.0497 (12)0.0266 (10)0.0061 (9)0.0151 (10)
C14B0.0575 (13)0.0978 (17)0.0533 (13)0.0379 (12)0.0023 (10)0.0224 (12)
C15B0.066 (8)0.143 (12)0.065 (5)0.045 (7)0.003 (5)0.046 (8)
C15C0.055 (6)0.126 (10)0.060 (5)0.039 (5)0.004 (4)0.039 (7)
C16B0.088 (9)0.154 (12)0.058 (5)0.066 (9)0.022 (5)0.048 (8)
C16C0.078 (8)0.159 (13)0.080 (7)0.062 (9)0.025 (6)0.052 (10)
C17B0.059 (10)0.148 (15)0.070 (7)0.046 (9)0.017 (7)0.040 (9)
C17C0.059 (11)0.17 (2)0.075 (6)0.066 (13)0.020 (8)0.056 (11)
C18B0.072 (2)0.135 (3)0.098 (3)0.057 (2)0.0121 (18)0.001 (3)
C19B0.0538 (14)0.0766 (15)0.0748 (16)0.0319 (12)0.0153 (12)0.0108 (13)
C20B0.0572 (15)0.0782 (17)0.0818 (18)0.0298 (13)0.0145 (13)0.0189 (14)
C21B0.079 (2)0.127 (3)0.087 (2)0.0608 (19)0.0094 (16)0.032 (2)
C22B0.094 (3)0.162 (4)0.108 (3)0.073 (3)0.016 (2)0.044 (3)
O500.075 (3)0.136 (5)0.094 (5)0.029 (3)0.003 (3)0.029 (4)
O50A0.127 (6)0.192 (7)0.096 (4)0.113 (6)0.026 (4)0.020 (5)
C500.104 (3)0.202 (4)0.098 (3)0.070 (3)0.011 (2)0.045 (3)
C510.129 (4)0.274 (6)0.129 (4)0.115 (4)0.010 (3)0.066 (4)
O600.072 (3)0.090 (3)0.169 (5)0.0003 (19)0.030 (3)0.087 (3)
O60A0.147 (8)0.276 (15)0.107 (7)0.071 (9)0.008 (6)0.112 (8)
C60A0.061 (5)0.170 (9)0.105 (7)0.022 (5)0.021 (5)0.086 (7)
C600.085 (4)0.095 (4)0.161 (7)0.028 (3)0.038 (4)0.033 (4)
C610.23 (3)0.32 (4)0.148 (16)0.21 (3)0.075 (17)0.16 (2)
C61A0.051 (3)0.127 (5)0.212 (10)0.011 (3)0.014 (4)0.108 (6)
Geometric parameters (Å, º) top
O1A—C7A1.214 (3)N7B—C12B1.368 (3)
O2A—C14A1.359 (3)N7B—N8B1.375 (2)
O2A—C17A1.365 (3)N7B—C8B1.391 (3)
O3A—C2A1.366 (3)N8B—C13B1.327 (3)
O3A—C18A1.406 (3)C1B—C6B1.365 (5)
N1A—C7A1.336 (3)C1B—C2B1.390 (4)
N1A—C3A1.412 (3)C1B—H120.87 (3)
N1A—H350.87 (3)C2B—C3B1.392 (3)
N2A—C8A1.364 (3)C3B—C4B1.377 (3)
N2A—C7A1.406 (3)C4B—C5B1.379 (3)
N2A—H70.84 (3)C4B—H130.93 (3)
N3A—C8A1.291 (3)C5B—C6B1.364 (4)
N3A—C9A1.374 (3)C5B—H370.98 (3)
N4A—C9A1.337 (3)C6B—H20.98 (3)
N4A—N5A1.366 (3)C9B—C11B1.404 (3)
N5A—C10A1.336 (3)C10B—C11B1.380 (3)
N5A—C19A1.468 (3)C10B—H90.96 (3)
N6A—C12A1.325 (3)C11B—C12B1.421 (3)
N6A—C13A1.366 (3)C13B—C14B1.439 (3)
N7A—C12A1.371 (3)C14B—C15C1.325 (19)
N7A—N8A1.373 (2)C14B—C15B1.384 (18)
N7A—C8A1.398 (3)C15B—C15C0.59 (2)
N8A—C13A1.329 (3)C15B—C16B1.36 (3)
C1A—C2A1.383 (3)C15B—C16C1.49 (3)
C1A—C6A1.388 (4)C15B—H320.92 (4)
C1A—H141.00 (3)C15C—C16C1.45 (3)
C2A—C3A1.399 (3)C15C—C16B1.58 (2)
C3A—C4A1.375 (3)C15C—H320.88 (4)
C4A—C5A1.395 (3)C16B—C16C0.64 (2)
C4A—H510.98 (3)C16B—C17B1.29 (5)
C5A—C6A1.363 (4)C16B—C17C1.44 (4)
C5A—H231.06 (3)C16B—H220.91 (5)
C6A—H260.99 (3)C16C—C17C1.31 (5)
C9A—C11A1.413 (3)C16C—C17B1.33 (5)
C10A—C11A1.373 (3)C16C—H221.03 (5)
C10A—H160.98 (3)C17B—H380.94 (5)
C11A—C12A1.418 (3)C17C—H380.97 (6)
C13A—C14A1.448 (3)C18B—H50.95 (3)
C14A—C15A1.339 (3)C18B—H401.14 (3)
C15A—C16A1.419 (4)C18B—H430.92 (3)
C15A—H290.95 (3)C19B—C20B1.502 (4)
C16A—C17A1.316 (4)C19B—H41.02 (2)
C16A—H281.00 (4)C19B—H301.00 (2)
C17A—H60.93 (3)C20B—C21B1.520 (3)
C18A—H80.97 (3)C20B—H110.96 (3)
C18A—H191.06 (4)C20B—H210.95 (3)
C18A—H250.99 (3)C21B—C22B1.516 (5)
C19A—C20A1.506 (4)C21B—H180.95 (3)
C19A—H101.02 (3)C21B—H421.10 (4)
C19A—H151.00 (3)C22B—H361.14 (5)
C20A—C21A1.512 (4)C22B—H410.95 (5)
C20A—H310.94 (3)C22B—H450.97 (4)
C20A—H341.07 (3)O50—O50A0.828 (8)
C21A—C22A1.512 (6)O50—C511.342 (9)
C21A—H271.08 (4)O50—C50i1.428 (8)
C21A—H480.89 (4)O50A—C511.367 (9)
C22A—H31.21 (4)O50A—C50i1.376 (8)
C22A—H390.93 (4)C50—O50Ai1.376 (8)
C22A—H440.90 (4)C50—O50i1.428 (8)
O1B—C7B1.217 (3)C50—C511.437 (6)
O2B—C17C1.29 (4)O60—O60A0.852 (11)
O2B—C14B1.357 (3)O60—C61Aii1.427 (10)
O2B—C17B1.47 (3)O60—C601.476 (9)
O3B—C2B1.374 (3)O60—C60A1.623 (12)
O3B—C18B1.418 (3)O60—C61ii1.69 (3)
N1B—C7B1.340 (3)O60A—C60A1.435 (15)
N1B—C3B1.410 (3)O60A—C61ii1.48 (3)
N1B—H200.86 (2)O60A—C61Aii1.514 (14)
N2B—C8B1.357 (3)O60A—C601.917 (14)
N2B—C7B1.401 (3)C60A—C61A1.164 (11)
N2B—H10.88 (2)C60A—C601.244 (11)
N3B—C8B1.293 (2)C60A—C611.56 (2)
N3B—C9B1.380 (3)C60—C611.26 (4)
N4B—C9B1.337 (3)C60—C61A1.341 (11)
N4B—N5B1.369 (3)C61—C61A0.60 (3)
N5B—C10B1.341 (3)C61—O60Aii1.48 (3)
N5B—C19B1.471 (3)C61—O60ii1.69 (3)
N6B—C12B1.322 (3)C61A—O60ii1.427 (9)
N6B—C13B1.367 (3)C61A—O60Aii1.514 (14)
C14A—O2A—C17A105.9 (2)C15C—C15B—C16B100 (4)
C2A—O3A—C18A119.4 (2)C15C—C15B—C14B72 (3)
C7A—N1A—C3A126.6 (2)C16B—C15B—C14B109.3 (16)
C7A—N1A—H35115.0 (17)C15C—C15B—C16C75 (4)
C3A—N1A—H35117.6 (17)C16B—C15B—C16C25.4 (11)
C8A—N2A—C7A129.4 (2)C14B—C15B—C16C98.9 (14)
C8A—N2A—H7115.0 (16)C15C—C15B—H3267 (4)
C7A—N2A—H7115.2 (16)C16B—C15B—H32127 (3)
C8A—N3A—C9A116.88 (18)C14B—C15B—H32114 (3)
C9A—N4A—N5A103.09 (17)C16C—C15B—H32116 (3)
C10A—N5A—N4A113.87 (19)C15B—C15C—C14B83 (4)
C10A—N5A—C19A127.9 (2)C15B—C15C—C16C82 (4)
N4A—N5A—C19A118.2 (2)C14B—C15C—C16C103.8 (16)
C12A—N6A—C13A102.87 (17)C15B—C15C—C16B58 (3)
C12A—N7A—N8A110.43 (16)C14B—C15C—C16B100.7 (13)
C12A—N7A—C8A123.98 (18)C16C—C15C—C16B23.9 (9)
N8A—N7A—C8A125.52 (17)C15B—C15C—H3274 (4)
C13A—N8A—N7A100.98 (17)C14B—C15C—H32123 (3)
C2A—C1A—C6A119.6 (3)C16C—C15C—H32123 (3)
C2A—C1A—H14116.8 (16)C16B—C15C—H32109 (3)
C6A—C1A—H14123.5 (16)C16C—C16B—C17B80 (4)
O3A—C2A—C1A126.1 (2)C16C—C16B—C15B89 (4)
O3A—C2A—C3A113.88 (19)C17B—C16B—C15B109 (2)
C1A—C2A—C3A120.1 (2)C16C—C16B—C17C65 (4)
C4A—C3A—C2A119.5 (2)C17B—C16B—C17C16 (3)
C4A—C3A—N1A125.7 (2)C15B—C16B—C17C101.6 (19)
C2A—C3A—N1A114.9 (2)C16C—C16B—C15C67 (3)
C3A—C4A—C5A120.2 (3)C17B—C16B—C15C105.2 (17)
C3A—C4A—H51121.6 (16)C15B—C16B—C15C21.8 (11)
C5A—C4A—H51118.2 (16)C17C—C16B—C15C93.2 (16)
C6A—C5A—C4A120.0 (3)C16C—C16B—H2281 (4)
C6A—C5A—H23123.1 (17)C17B—C16B—H22118 (4)
C4A—C5A—H23116.8 (17)C15B—C16B—H22129 (3)
C5A—C6A—C1A120.6 (2)C17C—C16B—H22118 (3)
C5A—C6A—H26118.4 (18)C15C—C16B—H22120 (3)
C1A—C6A—H26120.9 (18)C16B—C16C—C17C89 (5)
O1A—C7A—N1A126.8 (2)C16B—C16C—C17B72 (4)
O1A—C7A—N2A118.5 (2)C17C—C16C—C17B18 (3)
N1A—C7A—N2A114.8 (2)C16B—C16C—C15C89 (4)
N3A—C8A—N2A124.04 (19)C17C—C16C—C15C105 (2)
N3A—C8A—N7A121.70 (19)C17B—C16C—C15C110 (2)
N2A—C8A—N7A114.26 (19)C16B—C16C—C15B66 (3)
N4A—C9A—N3A123.30 (19)C17C—C16C—C15B102 (2)
N4A—C9A—C11A111.71 (19)C17B—C16C—C15B100 (2)
N3A—C9A—C11A125.0 (2)C15C—C16C—C15B23.2 (8)
N5A—C10A—C11A106.4 (2)C16B—C16C—H2261 (4)
N5A—C10A—H16122.6 (15)C17C—C16C—H22121 (3)
C11A—C10A—H16131.0 (15)C17B—C16C—H22106 (3)
C10A—C11A—C9A105.0 (2)C15C—C16C—H22122 (3)
C10A—C11A—C12A138.3 (2)C15B—C16C—H22108 (3)
C9A—C11A—C12A116.76 (19)C16B—C17B—C16C28.3 (14)
N6A—C12A—N7A109.37 (19)C16B—C17B—O2B108 (3)
N6A—C12A—C11A135.0 (2)C16C—C17B—O2B101 (2)
N7A—C12A—C11A115.59 (18)C16B—C17B—H38147 (5)
N8A—C13A—N6A116.35 (19)C16C—C17B—H38134 (5)
N8A—C13A—C14A123.6 (2)O2B—C17B—H38102 (4)
N6A—C13A—C14A120.02 (19)O2B—C17C—C16C113 (2)
C15A—C14A—O2A110.3 (2)O2B—C17C—C16B110 (2)
C15A—C14A—C13A131.4 (2)C16C—C17C—C16B26.3 (12)
O2A—C14A—C13A118.26 (19)O2B—C17C—H38114 (4)
C14A—C15A—C16A106.2 (3)C16C—C17C—H38132 (4)
C14A—C15A—H29124 (2)C16B—C17C—H38123 (3)
C16A—C15A—H29129.5 (19)O3B—C18B—H5100.4 (18)
C17A—C16A—C15A106.8 (3)O3B—C18B—H40104.8 (17)
C17A—C16A—H28126.4 (19)H5—C18B—H40121 (2)
C15A—C16A—H28126.7 (19)O3B—C18B—H43111 (2)
C16A—C17A—O2A110.8 (3)H5—C18B—H43108 (3)
C16A—C17A—H6137 (2)H40—C18B—H43111 (3)
O2A—C17A—H6112 (2)N5B—C19B—C20B111.9 (2)
O3A—C18A—H8113 (2)N5B—C19B—H4108.3 (13)
O3A—C18A—H19110.1 (18)C20B—C19B—H4111.7 (14)
H8—C18A—H19108 (3)N5B—C19B—H30105.1 (13)
O3A—C18A—H25106.3 (18)C20B—C19B—H30112.6 (13)
H8—C18A—H25110 (3)H4—C19B—H30106.8 (19)
H19—C18A—H25108 (2)C19B—C20B—C21B113.2 (2)
N5A—C19A—C20A112.5 (2)C19B—C20B—H11108.1 (16)
N5A—C19A—H10110.6 (16)C21B—C20B—H11108.5 (15)
C20A—C19A—H10108.9 (16)C19B—C20B—H21108.0 (15)
N5A—C19A—H15106.0 (18)C21B—C20B—H21109.3 (15)
C20A—C19A—H15111.6 (18)H11—C20B—H21110 (2)
H10—C19A—H15107 (2)C22B—C21B—C20B111.5 (3)
C19A—C20A—C21A113.4 (3)C22B—C21B—H18116 (2)
C19A—C20A—H31109.5 (16)C20B—C21B—H18108 (2)
C21A—C20A—H31109.6 (17)C22B—C21B—H42117 (2)
C19A—C20A—H34110.5 (15)C20B—C21B—H42106 (2)
C21A—C20A—H34106.4 (15)H18—C21B—H4297 (3)
H31—C20A—H34107 (2)C21B—C22B—H36112 (2)
C20A—C21A—C22A112.2 (3)C21B—C22B—H41111 (3)
C20A—C21A—H27108.7 (18)H36—C22B—H41107 (3)
C22A—C21A—H27113.5 (18)C21B—C22B—H45108 (2)
C20A—C21A—H48109 (2)H36—C22B—H45107 (3)
C22A—C21A—H48114 (3)H41—C22B—H45111 (3)
H27—C21A—H4899 (3)O50A—O50—C5173.9 (10)
C21A—C22A—H3108 (2)O50A—O50—C50i69.4 (9)
C21A—C22A—H39116 (3)C51—O50—C50i114.5 (5)
H3—C22A—H3999 (3)O50—O50A—C5170.6 (9)
C21A—C22A—H44112 (2)O50—O50A—C50i76.3 (10)
H3—C22A—H44108 (3)C51—O50A—C50i116.3 (5)
H39—C22A—H44112 (3)O50Ai—C50—O50i34.3 (3)
C17C—O2B—C14B106.4 (16)O50Ai—C50—C51116.0 (5)
C17C—O2B—C17B15 (3)O50i—C50—C51112.0 (4)
C14B—O2B—C17B105.5 (17)O50—C51—O50A35.6 (4)
C2B—O3B—C18B118.4 (3)O50—C51—C50116.8 (5)
C7B—N1B—C3B127.0 (2)O50A—C51—C50119.4 (5)
C7B—N1B—H20113.9 (16)O60A—O60—C61Aii78.9 (11)
C3B—N1B—H20119.1 (16)O60A—O60—C60107.9 (12)
C8B—N2B—C7B129.99 (18)C61Aii—O60—C60108.6 (6)
C8B—N2B—H1113.4 (15)O60A—O60—C60A61.9 (11)
C7B—N2B—H1116.5 (15)C61Aii—O60—C60A107.1 (5)
C8B—N3B—C9B116.14 (18)C60—O60—C60A47.0 (4)
C9B—N4B—N5B103.05 (17)O60A—O60—C61ii61.3 (18)
C10B—N5B—N4B113.87 (17)C61Aii—O60—C61ii20.0 (11)
C10B—N5B—C19B127.8 (2)C60—O60—C61ii121.3 (10)
N4B—N5B—C19B118.37 (18)C60A—O60—C61ii103.6 (17)
C12B—N6B—C13B102.85 (17)O60—O60A—C60A86.5 (13)
C12B—N7B—N8B110.53 (16)O60—O60A—C61ii88.4 (19)
C12B—N7B—C8B124.68 (17)C60A—O60A—C61ii126.3 (14)
N8B—N7B—C8B124.76 (17)O60—O60A—C61Aii67.6 (10)
C13B—N8B—N7B100.76 (16)C60A—O60A—C61Aii112.7 (7)
C6B—C1B—C2B120.6 (3)C61ii—O60A—C61Aii23.0 (12)
C6B—C1B—H12128 (2)O60—O60A—C6047.1 (9)
C2B—C1B—H12111 (2)C60A—O60A—C6040.4 (5)
O3B—C2B—C1B126.6 (2)C61ii—O60A—C60107.8 (11)
O3B—C2B—C3B113.9 (2)C61Aii—O60A—C6086.0 (6)
C1B—C2B—C3B119.5 (3)C61A—C60A—C6067.6 (7)
C4B—C3B—C2B118.8 (2)C61A—C60A—O60A121.0 (8)
C4B—C3B—N1B125.8 (2)C60—C60A—O60A91.1 (9)
C2B—C3B—N1B115.4 (2)C61A—C60A—C6119.0 (15)
C3B—C4B—C5B120.9 (3)C60—C60A—C6151.7 (17)
C3B—C4B—H13119.3 (17)O60A—C60A—C61124.8 (15)
C5B—C4B—H13119.7 (17)C61A—C60A—O60109.2 (8)
C6B—C5B—C4B120.1 (3)C60—C60A—O6060.3 (7)
C6B—C5B—H37121.0 (19)O60A—C60A—O6031.6 (5)
C4B—C5B—H37118.8 (19)C61—C60A—O60103.4 (18)
C1B—C6B—C5B120.1 (3)C60A—C60—C6177.4 (17)
C1B—C6B—H2120.6 (17)C60A—C60—C61A53.4 (6)
C5B—C6B—H2119.2 (17)C61—C60—C61A26.4 (14)
O1B—C7B—N1B126.6 (2)C60A—C60—O6072.7 (7)
O1B—C7B—N2B118.19 (18)C61—C60—O60132.2 (14)
N1B—C7B—N2B115.18 (19)C61A—C60—O60108.5 (7)
N3B—C8B—N2B124.54 (19)C60A—C60—O60A48.4 (6)
N3B—C8B—N7B121.84 (19)C61—C60—O60A112.0 (15)
N2B—C8B—N7B113.61 (17)C61A—C60—O60A86.2 (7)
N4B—C9B—N3B122.82 (19)O60—C60—O60A25.0 (5)
N4B—C9B—C11B111.92 (19)C61A—C61—C6085 (4)
N3B—C9B—C11B125.26 (18)C61A—C61—O60Aii82 (3)
N5B—C10B—C11B105.8 (2)C60—C61—O60Aii94 (3)
N5B—C10B—H9121.9 (15)C61A—C61—C60A39 (3)
C11B—C10B—H9132.3 (15)C60—C61—C60A50.9 (10)
C10B—C11B—C9B105.39 (19)O60Aii—C61—C60A102.9 (16)
C10B—C11B—C12B137.4 (2)C61A—C61—O60ii55 (3)
C9B—C11B—C12B117.17 (19)C60—C61—O60ii102.9 (19)
N6B—C12B—N7B109.42 (17)O60Aii—C61—O60ii30.3 (6)
N6B—C12B—C11B135.8 (2)C60A—C61—O60ii86.2 (12)
N7B—C12B—C11B114.81 (18)C61—C61A—C60A122 (4)
N8B—C13B—N6B116.44 (18)C61—C61A—C6069 (4)
N8B—C13B—C14B123.57 (19)C60A—C61A—C6059.0 (7)
N6B—C13B—C14B120.0 (2)C61—C61A—O60ii105 (3)
C15C—C14B—O2B111.0 (8)C60A—C61A—O60ii117.8 (8)
C15C—C14B—C15B25.2 (9)C60—C61A—O60ii113.7 (6)
O2B—C14B—C15B106.8 (8)C61—C61A—O60Aii75 (3)
C15C—C14B—C13B128.7 (8)C60A—C61A—O60Aii125.1 (7)
O2B—C14B—C13B119.2 (2)C60—C61A—O60Aii89.2 (8)
C15B—C14B—C13B131.6 (9)O60ii—C61A—O60Aii33.5 (5)
Symmetry codes: (i) x+3, y, z; (ii) x+2, y+1, z.
(compound4) N-[8-methyl-2-(2-furyl)-9-(methylthio)-8H-pyrazolo [4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl]N-(4-methoxyphenyl) urea hydrate top
Crystal data top
(C20H18N8SO3)·(H2O)Z = 2
Mr = 468.50F(000) = 488
Triclinic, P1Dx = 1.415 Mg m3
a = 10.1490 (3) ÅMo Kα radiation, λ = 0.71070 Å
b = 10.5112 (3) ÅCell parameters from 10025 reflections
c = 11.4025 (4) Åθ = 1–30°
α = 110.1850 (18)°µ = 0.19 mm1
β = 97.9640 (18)°T = 295 K
γ = 99.6510 (13)°Plate, colourless
V = 1099.89 (6) Å30.50 × 0.28 × 0.05 mm
Data collection top
Nonius Kappa CCD
diffractometer
2970 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 27.0°, θmin = 3.0°
ϕ scans and ω scansh = 1212
10025 measured reflectionsk = 1313
4777 independent reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0858P)2 + 0.3977P]
where P = (Fo2 + 2Fc2)/3
4777 reflections(Δ/σ)max = 0.001
381 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
(C20H18N8SO3)·(H2O)γ = 99.6510 (13)°
Mr = 468.50V = 1099.89 (6) Å3
Triclinic, P1Z = 2
a = 10.1490 (3) ÅMo Kα radiation
b = 10.5112 (3) ŵ = 0.19 mm1
c = 11.4025 (4) ÅT = 295 K
α = 110.1850 (18)°0.50 × 0.28 × 0.05 mm
β = 97.9640 (18)°
Data collection top
Nonius Kappa CCD
diffractometer
2970 reflections with I > 2σ(I)
10025 measured reflectionsRint = 0.028
4777 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.196H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.53 e Å3
4777 reflectionsΔρmin = 0.24 e Å3
381 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.66826 (10)0.04211 (9)0.38306 (9)0.0774 (3)
O10.3748 (3)0.7107 (3)0.1458 (3)0.0864 (7)
O20.1061 (2)0.4036 (2)0.5111 (2)0.0718 (6)
O30.8379 (3)0.9353 (3)0.1316 (2)0.0914 (8)
N10.5817 (3)0.6532 (3)0.1381 (3)0.0695 (7)
N20.4267 (3)0.5614 (3)0.2363 (3)0.0689 (7)
N30.6061 (3)0.4456 (2)0.2253 (2)0.0638 (6)
N40.7690 (3)0.3068 (3)0.2198 (2)0.0665 (7)
N50.7822 (3)0.2050 (3)0.2661 (2)0.0633 (6)
N60.3971 (2)0.2532 (2)0.4294 (2)0.0626 (6)
N70.4320 (2)0.3995 (2)0.3308 (2)0.0589 (6)
N80.3162 (2)0.4221 (2)0.3767 (2)0.0612 (6)
C10.8270 (4)0.7764 (4)0.0297 (3)0.0742 (9)
C20.7633 (4)0.7074 (3)0.0369 (3)0.0708 (9)
C30.6407 (3)0.7304 (3)0.0706 (3)0.0621 (8)
C40.5816 (4)0.8257 (3)0.0362 (3)0.0687 (8)
C50.6464 (4)0.8966 (3)0.0313 (3)0.0686 (9)
C60.7682 (4)0.8721 (3)0.0646 (3)0.0683 (8)
C70.4597 (4)0.6480 (3)0.1692 (3)0.0680 (8)
C80.4946 (3)0.4683 (3)0.2618 (3)0.0622 (7)
C90.6578 (3)0.3447 (3)0.2557 (3)0.0598 (7)
C100.6825 (3)0.1776 (3)0.3275 (3)0.0594 (7)
C110.5993 (3)0.2680 (3)0.3226 (3)0.0572 (7)
C120.4791 (3)0.2978 (3)0.3637 (3)0.0581 (7)
C130.3012 (3)0.3318 (3)0.4342 (3)0.0596 (7)
C140.1937 (3)0.3163 (3)0.5018 (3)0.0635 (8)
C150.1615 (4)0.2332 (4)0.5650 (4)0.0830 (10)
C160.0497 (4)0.2703 (5)0.6177 (4)0.0889 (11)
C170.0194 (4)0.3718 (4)0.5836 (4)0.0818 (10)
C180.8984 (4)0.1414 (4)0.2455 (4)0.0774 (10)
C190.7894 (6)1.0435 (5)0.1578 (5)0.0941 (12)
C200.6584 (5)0.1330 (5)0.5462 (4)0.0823 (10)
H10.358 (3)0.561 (3)0.259 (3)0.050 (9)*
H20.628 (4)0.604 (4)0.154 (4)0.093 (13)*
H30.199 (4)0.158 (4)0.562 (4)0.106 (13)*
H40.012 (4)0.232 (4)0.668 (4)0.095 (12)*
H50.054 (4)0.423 (4)0.596 (3)0.089 (11)*
H60.987 (5)0.210 (5)0.261 (4)0.113 (15)*
H70.922 (6)0.102 (6)0.313 (6)0.17 (2)*
H80.899 (5)0.083 (5)0.155 (5)0.139 (17)*
H90.493 (4)0.842 (3)0.062 (3)0.075 (10)*
H100.602 (3)0.960 (4)0.058 (3)0.082 (10)*
H110.909 (4)0.758 (4)0.050 (3)0.086 (11)*
H120.800 (3)0.649 (3)0.066 (3)0.079 (10)*
H130.785 (5)1.123 (5)0.074 (5)0.123 (16)*
H140.856 (4)1.071 (4)0.203 (4)0.101 (13)*
H150.697 (5)1.012 (5)0.209 (4)0.117 (16)*
H160.739 (5)0.215 (4)0.590 (4)0.102 (13)*
H170.574 (5)0.164 (5)0.544 (4)0.121 (15)*
H180.647 (5)0.058 (5)0.587 (5)0.142 (17)*
O1A0.1086 (5)0.5967 (5)0.0467 (5)0.0851 (13)0.50
O2A0.1332 (7)0.5957 (9)0.1852 (7)0.143 (3)0.50
H1A0.13110.62350.11460.12 (3)*0.50
H1B0.17680.61920.01600.10 (3)*0.50
H2A0.06010.50360.15030.050*0.50
H2B0.09350.62660.13570.050*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0945 (7)0.0691 (5)0.0858 (6)0.0371 (5)0.0209 (5)0.0413 (4)
O10.0879 (17)0.0813 (15)0.1128 (18)0.0414 (13)0.0195 (14)0.0548 (14)
O20.0646 (13)0.0661 (12)0.0954 (15)0.0231 (11)0.0219 (11)0.0380 (11)
O30.116 (2)0.0966 (17)0.1016 (18)0.0498 (16)0.0423 (15)0.0667 (15)
N10.0785 (19)0.0616 (15)0.0837 (18)0.0307 (14)0.0148 (14)0.0404 (14)
N20.0722 (19)0.0596 (15)0.0884 (19)0.0265 (14)0.0215 (16)0.0375 (14)
N30.0707 (17)0.0551 (14)0.0719 (15)0.0218 (12)0.0149 (13)0.0284 (12)
N40.0716 (17)0.0637 (15)0.0689 (15)0.0234 (13)0.0125 (12)0.0280 (12)
N50.0689 (16)0.0623 (14)0.0612 (14)0.0266 (12)0.0088 (12)0.0228 (12)
N60.0521 (14)0.0600 (14)0.0777 (16)0.0138 (11)0.0045 (12)0.0317 (12)
N70.0614 (15)0.0480 (12)0.0676 (14)0.0166 (11)0.0080 (11)0.0227 (11)
N80.0585 (15)0.0544 (13)0.0693 (14)0.0181 (11)0.0075 (11)0.0218 (11)
C10.092 (3)0.074 (2)0.078 (2)0.0409 (19)0.0264 (18)0.0401 (17)
C20.089 (2)0.0655 (18)0.0747 (19)0.0408 (17)0.0172 (17)0.0361 (16)
C30.080 (2)0.0492 (15)0.0585 (16)0.0186 (14)0.0041 (14)0.0242 (13)
C40.080 (2)0.0614 (17)0.0727 (19)0.0289 (16)0.0088 (16)0.0322 (15)
C50.088 (2)0.0581 (17)0.0663 (18)0.0269 (16)0.0035 (16)0.0316 (14)
C60.091 (2)0.0619 (17)0.0597 (16)0.0280 (17)0.0126 (16)0.0288 (14)
C70.081 (2)0.0546 (16)0.0711 (18)0.0245 (16)0.0086 (16)0.0259 (14)
C80.075 (2)0.0450 (14)0.0651 (17)0.0164 (14)0.0050 (14)0.0215 (13)
C90.0645 (18)0.0520 (15)0.0608 (16)0.0173 (14)0.0056 (13)0.0199 (13)
C100.0638 (18)0.0572 (16)0.0591 (16)0.0212 (14)0.0097 (13)0.0220 (13)
C110.0578 (17)0.0504 (15)0.0623 (16)0.0154 (13)0.0046 (13)0.0220 (12)
C120.0577 (17)0.0483 (14)0.0656 (16)0.0113 (13)0.0001 (13)0.0236 (13)
C130.0536 (16)0.0504 (15)0.0704 (17)0.0101 (13)0.0005 (13)0.0237 (13)
C140.0486 (16)0.0622 (17)0.0802 (19)0.0136 (13)0.0036 (14)0.0311 (15)
C150.064 (2)0.091 (3)0.116 (3)0.0243 (19)0.0134 (19)0.066 (2)
C160.072 (2)0.103 (3)0.116 (3)0.022 (2)0.028 (2)0.067 (3)
C170.067 (2)0.084 (2)0.107 (3)0.0202 (19)0.027 (2)0.046 (2)
C180.074 (2)0.089 (2)0.076 (2)0.043 (2)0.0164 (18)0.029 (2)
C190.119 (4)0.086 (3)0.103 (3)0.032 (3)0.022 (3)0.064 (3)
C200.076 (2)0.105 (3)0.078 (2)0.026 (2)0.0157 (19)0.047 (2)
O1A0.085 (3)0.081 (3)0.097 (3)0.014 (3)0.023 (3)0.045 (3)
O2A0.110 (5)0.187 (7)0.123 (5)0.056 (5)0.036 (4)0.033 (5)
Geometric parameters (Å, º) top
S1—C101.741 (3)C2—H120.90 (3)
S1—C201.800 (4)C3—C41.387 (4)
O1—C71.223 (4)C4—C51.397 (5)
O2—C171.364 (4)C4—H91.01 (4)
O2—C141.370 (4)C5—C61.382 (5)
O3—C61.366 (4)C5—H100.97 (4)
O3—C191.417 (4)C9—C111.405 (4)
N1—C71.332 (5)C10—C111.383 (4)
N1—C31.416 (4)C11—C121.411 (4)
N1—H20.80 (4)C13—C141.439 (4)
N2—C81.372 (4)C14—C151.339 (5)
N2—C71.405 (4)C15—C161.406 (6)
N2—H10.77 (3)C15—H30.93 (4)
N3—C81.290 (4)C16—C171.321 (5)
N3—C91.383 (3)C16—H40.90 (4)
N4—C91.329 (4)C17—H50.99 (4)
N4—N51.364 (3)C18—H61.01 (5)
N5—C101.354 (4)C18—H71.01 (6)
N5—C181.457 (4)C18—H81.00 (5)
N6—C121.326 (4)C19—H131.04 (5)
N6—C131.373 (4)C19—H140.97 (4)
N7—N81.374 (3)C19—H150.97 (5)
N7—C121.382 (3)C20—H161.00 (4)
N7—C81.388 (4)C20—H170.97 (5)
N8—C131.329 (4)C20—H181.04 (5)
C1—C21.371 (5)O1A—H1A0.953 (5)
C1—C61.392 (4)O1A—H1B0.859 (6)
C1—H110.93 (4)O2A—H2A1.029 (8)
C2—C31.387 (5)O2A—H2B0.833 (8)
C10—S1—C20100.75 (18)N3—C9—C11125.3 (3)
C17—O2—C14105.9 (3)N5—C10—C11105.6 (2)
C6—O3—C19117.7 (3)N5—C10—S1122.3 (2)
C7—N1—C3128.0 (3)C11—C10—S1131.9 (2)
C7—N1—H2119 (3)C10—C11—C9105.1 (3)
C3—N1—H2113 (3)C10—C11—C12137.5 (3)
C8—N2—C7129.4 (3)C9—C11—C12117.4 (2)
C8—N2—H1113 (2)N6—C12—N7109.2 (3)
C7—N2—H1117 (2)N6—C12—C11135.9 (3)
C8—N3—C9115.8 (3)N7—C12—C11114.9 (3)
C9—N4—N5103.4 (3)N8—C13—N6116.4 (3)
C10—N5—N4113.5 (2)N8—C13—C14123.5 (3)
C10—N5—C18128.6 (3)N6—C13—C14120.1 (3)
N4—N5—C18117.9 (3)C15—C14—O2109.7 (3)
C12—N6—C13102.9 (2)C15—C14—C13132.5 (3)
N8—N7—C12110.4 (2)O2—C14—C13117.8 (3)
N8—N7—C8125.6 (2)C14—C15—C16106.7 (3)
C12—N7—C8124.0 (3)C14—C15—H3125 (3)
C13—N8—N7101.1 (2)C16—C15—H3128 (3)
C2—C1—C6119.7 (4)C17—C16—C15107.2 (4)
C2—C1—H11119 (2)C17—C16—H4129 (3)
C6—C1—H11121 (2)C15—C16—H4124 (3)
C1—C2—C3121.5 (3)C16—C17—O2110.4 (4)
C1—C2—H12123 (2)C16—C17—H5133 (2)
C3—C2—H12116 (2)O2—C17—H5116 (2)
C2—C3—C4119.1 (3)N5—C18—H6114 (2)
C2—C3—N1117.5 (3)N5—C18—H7110 (3)
C4—C3—N1123.4 (3)H6—C18—H7100 (4)
C3—C4—C5119.6 (3)N5—C18—H8117 (3)
C3—C4—H9118.0 (19)H6—C18—H896 (4)
C5—C4—H9122.4 (19)H7—C18—H8117 (4)
C6—C5—C4120.6 (3)O3—C19—H13111 (3)
C6—C5—H10120 (2)O3—C19—H14102 (3)
C4—C5—H10119 (2)H13—C19—H14114 (3)
O3—C6—C5124.7 (3)O3—C19—H15112 (3)
O3—C6—C1115.8 (3)H13—C19—H15105 (4)
C5—C6—C1119.5 (3)H14—C19—H15112 (4)
O1—C7—N1126.8 (3)S1—C20—H16110 (2)
O1—C7—N2117.3 (3)S1—C20—H17107 (3)
N1—C7—N2115.9 (3)H16—C20—H17110 (4)
N3—C8—N2123.7 (3)S1—C20—H18106 (3)
N3—C8—N7122.5 (3)H16—C20—H18116 (3)
N2—C8—N7113.8 (3)H17—C20—H18107 (4)
N4—C9—N3122.3 (3)H1A—O1A—H1B113.4 (5)
N4—C9—C11112.4 (3)H2A—O2A—H2B92.7 (7)

Experimental details

(compound1)(compound2)(compound3)(compound4)
Crystal data
Chemical formula(C18H13O2N8Cl)·0.5(H2O)C22H22N8O3(C22H22N8O3)·0.5(C4H8O2)(C20H18N8SO3)·(H2O)
Mr417.82446.48490.53468.50
Crystal system, space groupTriclinic, P1Monoclinic, P21/cTriclinic, P1Triclinic, P1
Temperature (K)295295295295
a, b, c (Å)6.9825 (1), 15.7877 (3), 17.8780 (4)11.2816 (2), 24.0888 (5), 8.1651 (3)12.6218 (2), 14.0932 (3), 15.6948 (4)10.1490 (3), 10.5112 (3), 11.4025 (4)
α, β, γ (°)100.2320 (9), 95.906 (1), 100.567 (1)90, 103.9170 (8), 9072.8670 (7), 71.3280 (7), 70.6350 (9)110.1850 (18), 97.9640 (18), 99.6510 (13)
V3)1887.81 (6)2153.81 (10)2439.16 (9)1099.89 (6)
Z4442
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.240.100.100.19
Crystal size (mm)0.50 × 0.38 × 0.120.51 × 0.19 × 0.070.33 × 0.24 × 0.190.50 × 0.28 × 0.05
Data collection
DiffractometerNonius 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
14447, 8951, 6646 9542, 5159, 2594 15610, 10558, 6467 10025, 4777, 2970
Rint0.0220.0570.0240.028
(sin θ/λ)max1)0.6610.6610.6390.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.138, 1.06 0.060, 0.141, 1.02 0.061, 0.183, 1.04 0.058, 0.196, 1.11
No. of reflections89515159105584777
No. of parameters644396889381
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refinedH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.390.19, 0.240.27, 0.200.53, 0.24

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

 

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