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 A
1, A
2A, A
2B and A
3, 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 A
2A or A
3 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
CCDC references: 618457; 618458; 618459; 618460
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).
(compound1)
N-(8-methyl-2-(2-furyl)-8
H-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 = 417.82 | F(000) = 860 |
Triclinic, P1 | Dx = 1.470 Mg m−3 |
a = 6.9825 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.7877 (3) Å | Cell parameters from 14447 reflections |
c = 17.8780 (4) Å | θ = 3.4–28.0° |
α = 100.2320 (9)° | µ = 0.24 mm−1 |
β = 95.906 (1)° | T = 295 K |
γ = 100.567 (1)° | Plate, colourless |
V = 1887.81 (6) Å3 | 0.50 × 0.38 × 0.12 mm |
Data collection top
Nonius Kappa CCD diffractometer | 6646 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 28.0°, θmin = 3.4° |
ϕ scans and ω scans | h = −9→9 |
14447 measured reflections | k = −20→20 |
8951 independent reflections | l = −23→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)] = 0.048 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.138 | All 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 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
Crystal data top
(C18H13O2N8Cl)·0.5(H2O) | γ = 100.567 (1)° |
Mr = 417.82 | V = 1887.81 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 6.9825 (1) Å | Mo Kα radiation |
b = 15.7877 (3) Å | µ = 0.24 mm−1 |
c = 17.8780 (4) Å | T = 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 reflections | Rint = 0.022 |
8951 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.138 | All H-atom parameters refined |
S = 1.06 | Δρmax = 0.24 e Å−3 |
8951 reflections | Δρmin = −0.39 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1A | 1.43102 (8) | 0.15326 (4) | 0.11049 (3) | 0.06652 (16) | |
O1A | 1.2549 (2) | 0.08332 (9) | −0.18577 (7) | 0.0641 (4) | |
O2A | 0.8086 (3) | −0.34175 (11) | −0.30714 (10) | 0.0850 (5) | |
N1A | 1.3191 (2) | 0.09843 (9) | −0.05552 (8) | 0.0452 (3) | |
N2A | 1.1773 (2) | −0.03709 (10) | −0.13468 (9) | 0.0469 (3) | |
N3A | 1.2102 (2) | −0.05150 (10) | −0.00587 (8) | 0.0474 (3) | |
N4A | 1.2323 (3) | −0.08299 (12) | 0.11996 (9) | 0.0612 (4) | |
N5A | 1.1719 (3) | −0.15856 (14) | 0.14585 (10) | 0.0674 (5) | |
N6A | 0.9265 (2) | −0.30779 (10) | −0.09818 (10) | 0.0538 (4) | |
N7A | 1.0605 (2) | −0.17200 (9) | −0.10361 (8) | 0.0438 (3) | |
N8A | 0.9911 (2) | −0.21173 (9) | −0.17879 (9) | 0.0484 (3) | |
C1A | 1.5613 (3) | 0.30844 (15) | 0.07282 (15) | 0.0694 (6) | |
C2A | 1.4698 (3) | 0.22137 (13) | 0.04530 (11) | 0.0532 (4) | |
C3A | 1.4081 (2) | 0.18789 (11) | −0.03313 (10) | 0.0470 (4) | |
C4A | 1.4392 (3) | 0.24520 (13) | −0.08369 (13) | 0.0601 (5) | |
C5A | 1.5334 (4) | 0.33210 (15) | −0.05563 (18) | 0.0769 (7) | |
C6A | 1.5941 (4) | 0.36301 (17) | 0.02195 (18) | 0.0825 (7) | |
C7A | 1.2541 (3) | 0.05305 (11) | −0.12798 (10) | 0.0454 (4) | |
C8A | 1.1533 (2) | −0.08420 (11) | −0.07802 (10) | 0.0428 (3) | |
C9A | 1.1758 (2) | −0.10787 (12) | 0.04448 (10) | 0.0482 (4) | |
C10A | 1.0834 (3) | −0.22675 (17) | 0.09110 (13) | 0.0648 (5) | |
C11A | 1.0826 (3) | −0.19706 (13) | 0.02267 (11) | 0.0513 (4) | |
C12A | 1.0197 (2) | −0.23080 (12) | −0.05636 (11) | 0.0474 (4) | |
C13A | 0.9110 (3) | −0.29227 (12) | −0.17102 (11) | 0.0508 (4) | |
C14A | 0.8089 (3) | −0.36044 (13) | −0.23538 (13) | 0.0583 (5) | |
C15A | 0.7066 (4) | −0.44267 (17) | −0.2402 (2) | 0.0863 (8) | |
C16A | 0.6407 (4) | −0.4770 (2) | −0.3193 (2) | 0.0959 (10) | |
C17A | 0.7037 (5) | −0.4164 (2) | −0.3569 (2) | 0.1046 (10) | |
C18A | 1.2120 (7) | −0.1580 (3) | 0.22779 (16) | 0.0963 (10) | |
Cl1B | 1.26192 (8) | −0.19635 (4) | −0.57887 (3) | 0.07085 (17) | |
O1B | 1.2019 (2) | −0.10078 (9) | −0.29160 (7) | 0.0630 (4) | |
O2B | 1.2132 (3) | 0.34083 (10) | −0.21229 (10) | 0.0853 (5) | |
N1B | 1.2403 (2) | −0.12592 (10) | −0.41826 (9) | 0.0490 (3) | |
N2B | 1.2345 (2) | 0.01441 (10) | −0.35134 (9) | 0.0466 (3) | |
N3B | 1.2553 (2) | 0.01477 (10) | −0.48121 (8) | 0.0495 (3) | |
N4B | 1.2727 (2) | 0.03008 (12) | −0.61057 (9) | 0.0604 (4) | |
N5B | 1.2739 (3) | 0.10048 (14) | −0.64473 (9) | 0.0643 (5) | |
N6B | 1.2381 (2) | 0.27758 (11) | −0.41751 (10) | 0.0561 (4) | |
N7B | 1.2392 (2) | 0.14404 (9) | −0.39658 (8) | 0.0457 (3) | |
N8B | 1.2263 (2) | 0.19225 (10) | −0.32607 (8) | 0.0501 (3) | |
C1B | 1.2426 (4) | −0.34635 (18) | −0.52601 (18) | 0.0845 (8) | |
C2B | 1.2445 (3) | −0.25781 (14) | −0.50749 (12) | 0.0600 (5) | |
C3B | 1.2339 (3) | −0.21655 (12) | −0.43243 (11) | 0.0519 (4) | |
C4B | 1.2184 (4) | −0.26806 (15) | −0.37718 (15) | 0.0698 (6) | |
C5B | 1.2173 (5) | −0.35703 (17) | −0.3968 (2) | 0.0938 (9) | |
C6B | 1.2287 (5) | −0.3958 (2) | −0.4704 (2) | 0.1018 (10) | |
C7B | 1.2242 (3) | −0.07485 (11) | −0.35101 (9) | 0.0449 (4) | |
C8B | 1.2446 (2) | 0.05523 (11) | −0.41252 (9) | 0.0443 (4) | |
C9B | 1.2615 (2) | 0.06397 (13) | −0.53753 (10) | 0.0505 (4) | |
C10B | 1.2642 (3) | 0.17460 (17) | −0.59777 (12) | 0.0623 (5) | |
C11B | 1.2571 (3) | 0.15396 (13) | −0.52603 (10) | 0.0521 (4) | |
C12B | 1.2454 (2) | 0.19698 (13) | −0.45056 (11) | 0.0499 (4) | |
C13B | 1.2245 (3) | 0.27075 (12) | −0.34299 (11) | 0.0515 (4) | |
C14B | 1.2006 (3) | 0.34565 (13) | −0.28750 (12) | 0.0584 (5) | |
C15B | 1.1618 (4) | 0.42370 (16) | −0.29617 (18) | 0.0793 (7) | |
C16B | 1.1485 (4) | 0.46979 (18) | −0.2225 (2) | 0.0913 (9) | |
C17B | 1.1793 (5) | 0.41877 (18) | −0.1739 (2) | 0.0956 (9) | |
C18B | 1.2845 (5) | 0.0894 (3) | −0.72725 (14) | 0.0878 (9) | |
O1W | 0.8400 (6) | −0.4518 (2) | −0.0207 (2) | 0.1557 (13) | |
H1 | 1.153 (3) | −0.0637 (14) | −0.1812 (13) | 0.058 (6)* | |
H2 | 1.229 (3) | 0.0432 (14) | −0.3087 (12) | 0.054 (6)* | |
H3 | 1.402 (5) | 0.080 (2) | −0.7336 (17) | 0.106 (10)* | |
H4 | 1.399 (3) | 0.2254 (14) | −0.1351 (13) | 0.058 (6)* | |
H5 | 1.164 (6) | 0.038 (3) | −0.757 (2) | 0.146 (14)* | |
H6 | 1.207 (4) | −0.2492 (19) | −0.3300 (16) | 0.092 (9)* | |
H7 | 1.551 (4) | 0.3677 (19) | −0.0932 (15) | 0.092 (8)* | |
H8 | 1.247 (3) | −0.0988 (15) | −0.4564 (14) | 0.070 (7)* | |
H9 | 1.341 (7) | −0.139 (3) | 0.244 (2) | 0.153 (17)* | |
H10 | 1.136 (6) | −0.127 (3) | 0.253 (2) | 0.136 (15)* | |
H11 | 1.303 (3) | 0.0658 (14) | −0.0179 (12) | 0.061 (6)* | |
H12 | 1.653 (4) | 0.422 (2) | 0.0436 (17) | 0.105 (9)* | |
H13 | 1.268 (4) | 0.2315 (18) | −0.6170 (15) | 0.086 (8)* | |
H14 | 1.202 (5) | −0.386 (2) | −0.3582 (18) | 0.102 (10)* | |
H15 | 1.238 (5) | −0.453 (3) | −0.483 (2) | 0.130 (12)* | |
H16 | 1.038 (4) | −0.2814 (17) | 0.1059 (14) | 0.078 (7)* | |
H17 | 1.251 (4) | −0.3730 (19) | −0.5787 (17) | 0.098 (9)* | |
H18 | 0.564 (5) | −0.534 (2) | −0.3456 (17) | 0.109 (10)* | |
H19 | 1.257 (6) | 0.139 (3) | −0.745 (2) | 0.139 (13)* | |
H20 | 1.182 (6) | 0.423 (2) | −0.119 (2) | 0.137 (13)* | |
H21 | 0.698 (5) | −0.468 (2) | −0.1985 (18) | 0.110 (11)* | |
H22 | 1.127 (5) | 0.524 (2) | −0.2088 (18) | 0.111 (10)* | |
H23 | 1.599 (4) | 0.3296 (16) | 0.1299 (15) | 0.075 (7)* | |
H24 | 1.180 (6) | −0.217 (3) | 0.235 (2) | 0.136 (13)* | |
H25 | 1.133 (5) | 0.434 (2) | −0.3413 (18) | 0.106 (11)* | |
H26 | 0.702 (7) | −0.407 (3) | −0.416 (3) | 0.180 (18)* | |
H2W | 0.900 (8) | −0.489 (3) | −0.049 (3) | 0.17 (2)* | |
H1W | 0.862 (7) | −0.409 (3) | −0.060 (3) | 0.173 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1A | 0.0684 (3) | 0.0854 (4) | 0.0451 (2) | 0.0178 (3) | 0.0143 (2) | 0.0055 (2) |
O1A | 0.1004 (11) | 0.0461 (7) | 0.0424 (7) | 0.0056 (7) | 0.0000 (7) | 0.0149 (6) |
O2A | 0.1028 (13) | 0.0652 (10) | 0.0693 (10) | −0.0052 (9) | 0.0025 (9) | −0.0043 (8) |
N1A | 0.0502 (8) | 0.0431 (7) | 0.0412 (7) | 0.0060 (6) | 0.0063 (6) | 0.0097 (6) |
N2A | 0.0604 (9) | 0.0413 (7) | 0.0375 (7) | 0.0070 (6) | 0.0033 (6) | 0.0095 (6) |
N3A | 0.0535 (8) | 0.0513 (8) | 0.0407 (7) | 0.0125 (6) | 0.0120 (6) | 0.0131 (6) |
N4A | 0.0704 (10) | 0.0758 (11) | 0.0445 (8) | 0.0178 (8) | 0.0202 (7) | 0.0215 (8) |
N5A | 0.0733 (11) | 0.0878 (13) | 0.0508 (10) | 0.0161 (10) | 0.0212 (8) | 0.0324 (9) |
N6A | 0.0478 (8) | 0.0495 (8) | 0.0678 (10) | 0.0080 (6) | 0.0101 (7) | 0.0226 (7) |
N7A | 0.0423 (7) | 0.0448 (7) | 0.0459 (7) | 0.0086 (6) | 0.0073 (6) | 0.0132 (6) |
N8A | 0.0503 (8) | 0.0445 (8) | 0.0499 (8) | 0.0081 (6) | 0.0070 (6) | 0.0102 (6) |
C1A | 0.0583 (12) | 0.0632 (13) | 0.0737 (15) | 0.0056 (10) | 0.0056 (10) | −0.0113 (11) |
C2A | 0.0416 (8) | 0.0592 (11) | 0.0556 (10) | 0.0127 (7) | 0.0093 (7) | −0.0008 (8) |
C3A | 0.0391 (8) | 0.0454 (9) | 0.0548 (10) | 0.0082 (7) | 0.0079 (7) | 0.0053 (7) |
C4A | 0.0614 (11) | 0.0492 (10) | 0.0653 (13) | 0.0035 (8) | 0.0017 (9) | 0.0124 (9) |
C5A | 0.0776 (15) | 0.0517 (12) | 0.0967 (19) | 0.0004 (10) | 0.0060 (13) | 0.0193 (12) |
C6A | 0.0771 (15) | 0.0553 (13) | 0.098 (2) | −0.0024 (11) | 0.0018 (13) | −0.0075 (13) |
C7A | 0.0529 (9) | 0.0418 (8) | 0.0424 (9) | 0.0096 (7) | 0.0057 (7) | 0.0117 (7) |
C8A | 0.0429 (8) | 0.0433 (8) | 0.0453 (9) | 0.0109 (6) | 0.0094 (6) | 0.0128 (7) |
C9A | 0.0454 (9) | 0.0614 (11) | 0.0455 (9) | 0.0168 (8) | 0.0168 (7) | 0.0188 (8) |
C10A | 0.0625 (12) | 0.0772 (14) | 0.0638 (13) | 0.0108 (10) | 0.0189 (10) | 0.0365 (12) |
C11A | 0.0439 (9) | 0.0625 (11) | 0.0557 (10) | 0.0125 (8) | 0.0156 (7) | 0.0266 (9) |
C12A | 0.0390 (8) | 0.0508 (9) | 0.0591 (10) | 0.0116 (7) | 0.0126 (7) | 0.0232 (8) |
C13A | 0.0451 (9) | 0.0447 (9) | 0.0651 (11) | 0.0109 (7) | 0.0120 (8) | 0.0135 (8) |
C14A | 0.0509 (10) | 0.0474 (10) | 0.0744 (13) | 0.0083 (8) | 0.0104 (9) | 0.0072 (9) |
C15A | 0.0784 (16) | 0.0532 (13) | 0.121 (3) | 0.0005 (11) | 0.0194 (16) | 0.0108 (15) |
C16A | 0.0789 (17) | 0.0607 (15) | 0.124 (3) | −0.0037 (13) | 0.0096 (16) | −0.0229 (17) |
C17A | 0.107 (2) | 0.084 (2) | 0.095 (2) | −0.0037 (17) | 0.0019 (18) | −0.0254 (17) |
C18A | 0.125 (3) | 0.119 (3) | 0.0500 (14) | 0.015 (2) | 0.0216 (16) | 0.0376 (16) |
Cl1B | 0.0669 (3) | 0.0954 (4) | 0.0444 (3) | 0.0151 (3) | 0.0044 (2) | 0.0020 (2) |
O1B | 0.1017 (11) | 0.0488 (7) | 0.0430 (7) | 0.0149 (7) | 0.0216 (7) | 0.0151 (6) |
O2B | 0.1381 (16) | 0.0531 (9) | 0.0669 (10) | 0.0221 (9) | 0.0205 (10) | 0.0117 (7) |
N1B | 0.0586 (9) | 0.0481 (8) | 0.0416 (8) | 0.0090 (6) | 0.0133 (6) | 0.0104 (6) |
N2B | 0.0593 (9) | 0.0454 (8) | 0.0365 (7) | 0.0094 (6) | 0.0106 (6) | 0.0110 (6) |
N3B | 0.0531 (8) | 0.0584 (9) | 0.0386 (7) | 0.0091 (7) | 0.0079 (6) | 0.0154 (6) |
N4B | 0.0597 (9) | 0.0848 (12) | 0.0389 (8) | 0.0136 (8) | 0.0045 (7) | 0.0214 (8) |
N5B | 0.0609 (10) | 0.0995 (14) | 0.0399 (8) | 0.0197 (9) | 0.0065 (7) | 0.0302 (9) |
N6B | 0.0559 (9) | 0.0578 (9) | 0.0619 (10) | 0.0134 (7) | 0.0131 (7) | 0.0266 (8) |
N7B | 0.0486 (7) | 0.0506 (8) | 0.0413 (7) | 0.0101 (6) | 0.0094 (6) | 0.0169 (6) |
N8B | 0.0559 (8) | 0.0488 (8) | 0.0466 (8) | 0.0092 (6) | 0.0088 (6) | 0.0129 (6) |
C1B | 0.0922 (18) | 0.0722 (16) | 0.0810 (17) | 0.0244 (13) | 0.0118 (14) | −0.0133 (14) |
C2B | 0.0516 (10) | 0.0655 (12) | 0.0562 (11) | 0.0106 (9) | 0.0054 (8) | −0.0023 (9) |
C3B | 0.0492 (9) | 0.0493 (10) | 0.0560 (10) | 0.0089 (7) | 0.0109 (8) | 0.0064 (8) |
C4B | 0.0912 (16) | 0.0546 (12) | 0.0696 (14) | 0.0191 (11) | 0.0277 (12) | 0.0147 (11) |
C5B | 0.133 (3) | 0.0565 (14) | 0.104 (2) | 0.0301 (15) | 0.0394 (19) | 0.0236 (15) |
C6B | 0.132 (3) | 0.0558 (15) | 0.116 (3) | 0.0297 (16) | 0.024 (2) | −0.0018 (16) |
C7B | 0.0493 (9) | 0.0460 (9) | 0.0401 (8) | 0.0072 (7) | 0.0089 (7) | 0.0114 (7) |
C8B | 0.0424 (8) | 0.0507 (9) | 0.0413 (8) | 0.0069 (7) | 0.0066 (6) | 0.0150 (7) |
C9B | 0.0424 (8) | 0.0705 (12) | 0.0411 (9) | 0.0089 (8) | 0.0053 (7) | 0.0209 (8) |
C10B | 0.0574 (11) | 0.0866 (15) | 0.0531 (11) | 0.0195 (10) | 0.0106 (9) | 0.0346 (11) |
C11B | 0.0456 (9) | 0.0702 (12) | 0.0477 (10) | 0.0125 (8) | 0.0085 (7) | 0.0288 (9) |
C12B | 0.0434 (9) | 0.0601 (11) | 0.0528 (10) | 0.0107 (7) | 0.0092 (7) | 0.0273 (8) |
C13B | 0.0516 (10) | 0.0491 (10) | 0.0570 (10) | 0.0085 (7) | 0.0088 (8) | 0.0202 (8) |
C14B | 0.0624 (11) | 0.0489 (10) | 0.0655 (12) | 0.0086 (8) | 0.0109 (9) | 0.0174 (9) |
C15B | 0.0911 (18) | 0.0568 (13) | 0.0921 (19) | 0.0220 (12) | 0.0008 (14) | 0.0206 (13) |
C16B | 0.0935 (19) | 0.0510 (13) | 0.127 (3) | 0.0213 (12) | 0.0160 (16) | 0.0038 (15) |
C17B | 0.134 (3) | 0.0572 (14) | 0.090 (2) | 0.0120 (15) | 0.0316 (18) | −0.0022 (14) |
C18B | 0.092 (2) | 0.148 (3) | 0.0432 (12) | 0.049 (2) | 0.0150 (12) | 0.0417 (15) |
O1W | 0.220 (4) | 0.1006 (19) | 0.176 (3) | 0.024 (2) | 0.090 (3) | 0.077 (2) |
Geometric parameters (Å, º) top
Cl1A—C2A | 1.730 (2) | O1B—C7B | 1.219 (2) |
O1A—C7A | 1.213 (2) | O2B—C14B | 1.355 (3) |
O2A—C14A | 1.366 (3) | O2B—C17B | 1.371 (3) |
O2A—C17A | 1.376 (3) | N1B—C7B | 1.351 (2) |
N1A—C7A | 1.352 (2) | N1B—C3B | 1.400 (2) |
N1A—C3A | 1.403 (2) | N1B—H8 | 0.87 (2) |
N1A—H11 | 0.92 (2) | N2B—C8B | 1.366 (2) |
N2A—C8A | 1.365 (2) | N2B—C7B | 1.399 (2) |
N2A—C7A | 1.405 (2) | N2B—H2 | 0.82 (2) |
N2A—H1 | 0.85 (2) | N3B—C8B | 1.296 (2) |
N3A—C8A | 1.293 (2) | N3B—C9B | 1.376 (2) |
N3A—C9A | 1.382 (2) | N4B—C9B | 1.336 (2) |
N4A—C9A | 1.333 (2) | N4B—N5B | 1.359 (2) |
N4A—N5A | 1.366 (2) | N5B—C10B | 1.331 (3) |
N5A—C10A | 1.325 (3) | N5B—C18B | 1.466 (3) |
N5A—C18A | 1.461 (3) | N6B—C12B | 1.317 (3) |
N6A—C12A | 1.321 (2) | N6B—C13B | 1.367 (2) |
N6A—C13A | 1.364 (2) | N7B—N8B | 1.373 (2) |
N7A—C12A | 1.374 (2) | N7B—C12B | 1.383 (2) |
N7A—N8A | 1.375 (2) | N7B—C8B | 1.388 (2) |
N7A—C8A | 1.391 (2) | N8B—C13B | 1.329 (2) |
N8A—C13A | 1.329 (2) | C1B—C6B | 1.369 (4) |
C1A—C6A | 1.368 (4) | C1B—C2B | 1.375 (3) |
C1A—C2A | 1.383 (3) | C1B—H17 | 0.97 (3) |
C1A—H23 | 1.01 (2) | C2B—C3B | 1.399 (3) |
C2A—C3A | 1.400 (3) | C3B—C4B | 1.387 (3) |
C3A—C4A | 1.393 (3) | C4B—C5B | 1.384 (3) |
C4A—C5A | 1.387 (3) | C4B—H6 | 0.86 (3) |
C4A—H4 | 0.91 (2) | C5B—C6B | 1.366 (4) |
C5A—C6A | 1.380 (4) | C5B—H14 | 0.90 (3) |
C5A—H7 | 0.95 (3) | C6B—H15 | 0.91 (4) |
C6A—H12 | 0.94 (3) | C9B—C11B | 1.405 (3) |
C9A—C11A | 1.405 (3) | C10B—C11B | 1.382 (3) |
C10A—C11A | 1.385 (3) | C10B—H13 | 1.01 (3) |
C10A—H16 | 0.95 (3) | C11B—C12B | 1.416 (3) |
C11A—C12A | 1.411 (3) | C13B—C14B | 1.449 (3) |
C13A—C14A | 1.449 (3) | C14B—C15B | 1.341 (3) |
C14A—C15A | 1.346 (3) | C15B—C16B | 1.407 (4) |
C15A—C16A | 1.417 (5) | C15B—H25 | 0.86 (3) |
C15A—H21 | 0.91 (3) | C16B—C17B | 1.313 (4) |
C16A—C17A | 1.303 (5) | C16B—H22 | 0.89 (3) |
C16A—H18 | 0.97 (3) | C17B—H20 | 0.97 (4) |
C17A—H26 | 1.10 (4) | C18B—H3 | 0.87 (3) |
C18A—H9 | 0.90 (5) | C18B—H5 | 1.07 (4) |
C18A—H10 | 0.88 (4) | C18B—H19 | 0.94 (4) |
C18A—H24 | 0.96 (4) | O1W—H2W | 0.90 (5) |
Cl1B—C2B | 1.736 (2) | O1W—H1W | 1.06 (5) |
| | | |
C14A—O2A—C17A | 105.9 (2) | C7B—N1B—C3B | 126.76 (16) |
C7A—N1A—C3A | 126.80 (15) | C7B—N1B—H8 | 114.5 (16) |
C7A—N1A—H11 | 114.9 (13) | C3B—N1B—H8 | 118.6 (16) |
C3A—N1A—H11 | 118.3 (13) | C8B—N2B—C7B | 127.96 (15) |
C8A—N2A—C7A | 128.89 (15) | C8B—N2B—H2 | 119.5 (14) |
C8A—N2A—H1 | 119.5 (14) | C7B—N2B—H2 | 112.5 (14) |
C7A—N2A—H1 | 111.4 (14) | C8B—N3B—C9B | 116.89 (16) |
C8A—N3A—C9A | 116.96 (15) | C9B—N4B—N5B | 102.54 (17) |
C9A—N4A—N5A | 102.68 (17) | C10B—N5B—N4B | 114.69 (16) |
C10A—N5A—N4A | 114.18 (17) | C10B—N5B—C18B | 126.2 (2) |
C10A—N5A—C18A | 126.7 (2) | N4B—N5B—C18B | 119.2 (2) |
N4A—N5A—C18A | 119.1 (2) | C12B—N6B—C13B | 102.81 (15) |
C12A—N6A—C13A | 103.06 (15) | N8B—N7B—C12B | 109.94 (14) |
C12A—N7A—N8A | 110.29 (14) | N8B—N7B—C8B | 125.74 (14) |
C12A—N7A—C8A | 124.32 (15) | C12B—N7B—C8B | 124.32 (15) |
N8A—N7A—C8A | 125.35 (14) | C13B—N8B—N7B | 100.99 (14) |
C13A—N8A—N7A | 100.92 (14) | C6B—C1B—C2B | 119.8 (3) |
C6A—C1A—C2A | 119.1 (2) | C6B—C1B—H17 | 120.9 (17) |
C6A—C1A—H23 | 122.3 (14) | C2B—C1B—H17 | 119.3 (17) |
C2A—C1A—H23 | 118.6 (14) | C1B—C2B—C3B | 121.3 (2) |
C1A—C2A—C3A | 121.7 (2) | C1B—C2B—Cl1B | 119.06 (19) |
C1A—C2A—Cl1A | 118.38 (17) | C3B—C2B—Cl1B | 119.63 (16) |
C3A—C2A—Cl1A | 119.87 (15) | C4B—C3B—C2B | 117.89 (19) |
C4A—C3A—C2A | 118.14 (17) | C4B—C3B—N1B | 124.49 (18) |
C4A—C3A—N1A | 124.36 (17) | C2B—C3B—N1B | 117.62 (18) |
C2A—C3A—N1A | 117.51 (17) | C5B—C4B—C3B | 120.0 (2) |
C5A—C4A—C3A | 119.7 (2) | C5B—C4B—H6 | 115.2 (19) |
C5A—C4A—H4 | 120.2 (14) | C3B—C4B—H6 | 124.8 (19) |
C3A—C4A—H4 | 120.1 (13) | C6B—C5B—C4B | 121.1 (3) |
C6A—C5A—C4A | 120.8 (3) | C6B—C5B—H14 | 124 (2) |
C6A—C5A—H7 | 123.6 (17) | C4B—C5B—H14 | 115 (2) |
C4A—C5A—H7 | 115.5 (17) | C5B—C6B—C1B | 119.9 (3) |
C1A—C6A—C5A | 120.5 (2) | C5B—C6B—H15 | 122 (2) |
C1A—C6A—H12 | 115.7 (18) | C1B—C6B—H15 | 118 (2) |
C5A—C6A—H12 | 123.7 (19) | O1B—C7B—N1B | 125.08 (16) |
O1A—C7A—N1A | 126.04 (16) | O1B—C7B—N2B | 118.85 (16) |
O1A—C7A—N2A | 118.72 (15) | N1B—C7B—N2B | 116.06 (15) |
N1A—C7A—N2A | 115.23 (15) | N3B—C8B—N2B | 123.22 (16) |
N3A—C8A—N2A | 123.90 (15) | N3B—C8B—N7B | 121.52 (15) |
N3A—C8A—N7A | 121.40 (15) | N2B—C8B—N7B | 115.25 (15) |
N2A—C8A—N7A | 114.70 (15) | N4B—C9B—N3B | 122.73 (18) |
N4A—C9A—N3A | 122.85 (17) | N4B—C9B—C11B | 112.25 (16) |
N4A—C9A—C11A | 112.49 (16) | N3B—C9B—C11B | 125.03 (17) |
N3A—C9A—C11A | 124.65 (16) | N5B—C10B—C11B | 105.80 (19) |
N5A—C10A—C11A | 106.4 (2) | N5B—C10B—H13 | 121.1 (15) |
N5A—C10A—H16 | 117.8 (15) | C11B—C10B—H13 | 133.0 (15) |
C11A—C10A—H16 | 135.9 (15) | C10B—C11B—C9B | 104.71 (19) |
C10A—C11A—C9A | 104.29 (19) | C10B—C11B—C12B | 138.1 (2) |
C10A—C11A—C12A | 138.5 (2) | C9B—C11B—C12B | 117.22 (15) |
C9A—C11A—C12A | 117.22 (16) | N6B—C12B—N7B | 109.62 (16) |
N6A—C12A—N7A | 109.34 (16) | N6B—C12B—C11B | 135.35 (17) |
N6A—C12A—C11A | 135.22 (17) | N7B—C12B—C11B | 115.03 (16) |
N7A—C12A—C11A | 115.43 (16) | N8B—C13B—N6B | 116.63 (17) |
N8A—C13A—N6A | 116.37 (17) | N8B—C13B—C14B | 123.02 (17) |
N8A—C13A—C14A | 122.73 (18) | N6B—C13B—C14B | 120.29 (16) |
N6A—C13A—C14A | 120.89 (17) | C15B—C14B—O2B | 109.5 (2) |
C15A—C14A—O2A | 109.7 (2) | C15B—C14B—C13B | 131.4 (2) |
C15A—C14A—C13A | 132.7 (2) | O2B—C14B—C13B | 119.02 (17) |
O2A—C14A—C13A | 117.64 (17) | C14B—C15B—C16B | 106.7 (3) |
C14A—C15A—C16A | 106.2 (3) | C14B—C15B—H25 | 121 (2) |
C14A—C15A—H21 | 122 (2) | C16B—C15B—H25 | 132 (2) |
C16A—C15A—H21 | 131 (2) | C17B—C16B—C15B | 107.3 (2) |
C17A—C16A—C15A | 107.7 (3) | C17B—C16B—H22 | 124 (2) |
C17A—C16A—H18 | 121.4 (18) | C15B—C16B—H22 | 129 (2) |
C15A—C16A—H18 | 130.9 (18) | C16B—C17B—O2B | 110.0 (3) |
C16A—C17A—O2A | 110.5 (3) | C16B—C17B—H20 | 136 (2) |
C16A—C17A—H26 | 139 (2) | O2B—C17B—H20 | 114 (2) |
O2A—C17A—H26 | 110 (2) | N5B—C18B—H3 | 106 (2) |
N5A—C18A—H9 | 110 (3) | N5B—C18B—H5 | 108 (2) |
N5A—C18A—H10 | 109 (3) | H3—C18B—H5 | 116 (3) |
H9—C18A—H10 | 114 (4) | N5B—C18B—H19 | 110 (2) |
N5A—C18A—H24 | 109 (2) | H3—C18B—H19 | 114 (3) |
H9—C18A—H24 | 106 (3) | H5—C18B—H19 | 103 (3) |
H10—C18A—H24 | 108 (3) | H2W—O1W—H1W | 89 (4) |
C14B—O2B—C17B | 106.4 (2) | | |
(compound2)
N-[8-butyl-2-(2-furyl)-8
H-pyrazolo[4,3-
e][1,2,4]triazolo [1,5-
c]pyrimidin-5-yl]
N-(3-methoxyphenyl)-urea
top
Crystal data top
C22H22N8O3 | F(000) = 936 |
Mr = 446.48 | Dx = 1.377 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.2816 (2) Å | Cell parameters from 9542 reflections |
b = 24.0888 (5) Å | θ = 2.7–28.0° |
c = 8.1651 (3) Å | µ = 0.10 mm−1 |
β = 103.9170 (8)° | T = 295 K |
V = 2153.81 (10) Å3 | Plate, colourless |
Z = 4 | 0.51 × 0.19 × 0.07 mm |
Data collection top
Nonius Kappa CCD diffractometer | 2594 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.057 |
Graphite monochromator | θmax = 28.0°, θmin = 2.7° |
ϕ scans and ω scans | h = −14→14 |
9542 measured reflections | k = −30→31 |
5159 independent reflections | l = −10→10 |
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)] = 0.060 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.141 | All 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 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Crystal data top
C22H22N8O3 | V = 2153.81 (10) Å3 |
Mr = 446.48 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.2816 (2) Å | µ = 0.10 mm−1 |
b = 24.0888 (5) Å | T = 295 K |
c = 8.1651 (3) Å | 0.51 × 0.19 × 0.07 mm |
β = 103.9170 (8)° | |
Data collection top
Nonius Kappa CCD diffractometer | 2594 reflections with I > 2σ(I) |
9542 measured reflections | Rint = 0.057 |
5159 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.141 | All H-atom parameters refined |
S = 1.02 | Δρmax = 0.19 e Å−3 |
5159 reflections | Δρmin = −0.24 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | −0.03830 (15) | −0.05812 (7) | 0.7801 (2) | 0.0621 (5) | |
O2 | −0.49327 (17) | 0.05909 (7) | 1.0177 (2) | 0.0737 (6) | |
O3 | 0.25764 (15) | −0.14966 (7) | 0.5524 (2) | 0.0673 (5) | |
N1 | 0.07798 (17) | 0.01383 (9) | 0.7218 (2) | 0.0505 (5) | |
N2 | −0.09438 (18) | 0.02939 (8) | 0.8222 (2) | 0.0505 (5) | |
N3 | −0.00331 (16) | 0.11552 (7) | 0.7922 (2) | 0.0451 (5) | |
N4 | 0.06447 (16) | 0.20783 (8) | 0.7643 (2) | 0.0459 (5) | |
N5 | 0.01815 (16) | 0.25837 (7) | 0.7913 (2) | 0.0448 (5) | |
N6 | −0.30006 (16) | 0.17494 (8) | 0.9565 (2) | 0.0464 (5) | |
N7 | −0.27852 (16) | 0.08103 (8) | 0.9248 (2) | 0.0462 (5) | |
N8 | −0.18402 (16) | 0.11008 (7) | 0.8847 (2) | 0.0426 (4) | |
C1 | 0.2653 (2) | −0.09355 (9) | 0.5745 (3) | 0.0482 (6) | |
C2 | 0.1711 (2) | −0.06997 (10) | 0.6339 (3) | 0.0486 (6) | |
C3 | 0.16903 (19) | −0.01402 (9) | 0.6605 (3) | 0.0440 (5) | |
C4 | 0.2591 (3) | 0.01922 (12) | 0.6253 (4) | 0.0749 (9) | |
C5 | 0.3534 (12) | −0.0044 (3) | 0.578 (4) | 0.102 (3) | 0.84 (6) |
C5A | 0.342 (2) | −0.0062 (15) | 0.520 (3) | 0.030 (11) | 0.16 (6) |
C6 | 0.3551 (3) | −0.06115 (12) | 0.5399 (4) | 0.0732 (8) | |
C7 | −0.0158 (2) | −0.00908 (10) | 0.7718 (3) | 0.0465 (5) | |
C8 | −0.08811 (19) | 0.08572 (9) | 0.8309 (3) | 0.0423 (5) | |
C9 | −0.01466 (19) | 0.17222 (9) | 0.8051 (2) | 0.0403 (5) | |
C10 | −0.0839 (2) | 0.25557 (10) | 0.8476 (3) | 0.0458 (5) | |
C11 | −0.10892 (18) | 0.19987 (9) | 0.8592 (2) | 0.0406 (5) | |
C12 | −0.19919 (19) | 0.16606 (9) | 0.9041 (3) | 0.0413 (5) | |
C13 | −0.3437 (2) | 0.12249 (9) | 0.9663 (3) | 0.0443 (5) | |
C14 | −0.4572 (2) | 0.11279 (10) | 1.0154 (3) | 0.0496 (6) | |
C15 | −0.5400 (2) | 0.14631 (13) | 1.0563 (3) | 0.0624 (7) | |
C16 | −0.6341 (3) | 0.11167 (15) | 1.0853 (4) | 0.0787 (9) | |
C17 | −0.6028 (3) | 0.06001 (17) | 1.0608 (4) | 0.0890 (10) | |
C18 | 0.3587 (3) | −0.17815 (14) | 0.5140 (5) | 0.0661 (8) | |
C19 | 0.0816 (2) | 0.30892 (10) | 0.7589 (3) | 0.0490 (6) | |
C20 | 0.1728 (2) | 0.33018 (10) | 0.9123 (3) | 0.0505 (6) | |
C21 | 0.2812 (3) | 0.29260 (13) | 0.9779 (4) | 0.0635 (7) | |
C22 | 0.3661 (3) | 0.31516 (19) | 1.1360 (5) | 0.0816 (9) | |
H1 | 0.2045 (18) | 0.3673 (9) | 0.888 (2) | 0.047 (6)* | |
H2 | 0.1304 (19) | 0.3367 (9) | 1.004 (3) | 0.054 (6)* | |
H3 | −0.1276 (19) | 0.2884 (10) | 0.873 (2) | 0.054 (6)* | |
H4 | 0.255 (3) | 0.0567 (12) | 0.645 (3) | 0.084 (9)* | |
H5 | 0.410 (3) | 0.0174 (14) | 0.539 (4) | 0.108 (11)* | |
H6 | 0.375 (3) | −0.1645 (12) | 0.407 (4) | 0.097 (10)* | |
H7 | 0.417 (2) | −0.0785 (11) | 0.496 (3) | 0.081 (8)* | |
H8 | 0.110 (2) | −0.0931 (10) | 0.654 (3) | 0.058 (7)* | |
H9 | 0.396 (3) | 0.3537 (15) | 1.114 (4) | 0.102 (11)* | |
H10 | 0.433 (3) | −0.1706 (11) | 0.604 (4) | 0.088 (10)* | |
H11 | −0.162 (2) | 0.0128 (10) | 0.843 (3) | 0.068 (8)* | |
H12 | 0.014 (2) | 0.3381 (11) | 0.720 (3) | 0.068 (7)* | |
H13 | 0.337 (3) | −0.2191 (15) | 0.511 (4) | 0.116 (12)* | |
H14 | 0.322 (2) | 0.2876 (11) | 0.889 (3) | 0.076 (8)* | |
H15 | 0.080 (2) | 0.0508 (12) | 0.720 (3) | 0.082 (9)* | |
H16 | 0.315 (3) | 0.3211 (13) | 1.218 (4) | 0.115 (12)* | |
H17 | 0.254 (2) | 0.2546 (12) | 1.001 (3) | 0.077 (8)* | |
H18 | −0.536 (2) | 0.1835 (10) | 1.060 (3) | 0.055 (7)* | |
H19 | 0.122 (2) | 0.2982 (9) | 0.669 (3) | 0.055 (6)* | |
H20 | −0.702 (3) | 0.1207 (12) | 1.112 (4) | 0.091 (10)* | |
H21 | −0.644 (3) | 0.0221 (15) | 1.066 (4) | 0.123 (12)* | |
H22 | 0.436 (3) | 0.2914 (14) | 1.171 (4) | 0.105 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0685 (11) | 0.0303 (10) | 0.0978 (13) | −0.0033 (8) | 0.0402 (10) | −0.0052 (8) |
O2 | 0.0693 (11) | 0.0506 (12) | 0.1187 (15) | −0.0103 (9) | 0.0570 (11) | −0.0127 (10) |
O3 | 0.0671 (11) | 0.0392 (11) | 0.1095 (14) | 0.0025 (9) | 0.0482 (10) | −0.0109 (9) |
N1 | 0.0517 (12) | 0.0297 (12) | 0.0769 (13) | 0.0011 (10) | 0.0291 (10) | −0.0019 (10) |
N2 | 0.0516 (12) | 0.0306 (12) | 0.0768 (14) | −0.0038 (10) | 0.0301 (11) | −0.0054 (9) |
N3 | 0.0489 (11) | 0.0323 (11) | 0.0585 (12) | −0.0011 (9) | 0.0214 (9) | −0.0043 (8) |
N4 | 0.0531 (11) | 0.0316 (11) | 0.0572 (11) | −0.0018 (9) | 0.0210 (9) | −0.0033 (9) |
N5 | 0.0531 (11) | 0.0329 (11) | 0.0513 (11) | −0.0013 (9) | 0.0182 (9) | −0.0012 (8) |
N6 | 0.0498 (11) | 0.0364 (12) | 0.0576 (12) | 0.0011 (9) | 0.0219 (9) | −0.0016 (9) |
N7 | 0.0489 (11) | 0.0376 (11) | 0.0569 (11) | −0.0033 (9) | 0.0222 (9) | 0.0001 (9) |
N8 | 0.0436 (10) | 0.0323 (11) | 0.0555 (11) | −0.0004 (9) | 0.0188 (9) | −0.0010 (8) |
C1 | 0.0527 (14) | 0.0346 (14) | 0.0607 (14) | 0.0009 (11) | 0.0202 (11) | −0.0003 (11) |
C2 | 0.0535 (15) | 0.0353 (15) | 0.0634 (15) | −0.0008 (12) | 0.0267 (12) | −0.0004 (11) |
C3 | 0.0447 (13) | 0.0343 (14) | 0.0554 (13) | 0.0012 (11) | 0.0168 (10) | 0.0034 (10) |
C4 | 0.0732 (19) | 0.0337 (17) | 0.134 (3) | −0.0023 (14) | 0.0558 (19) | −0.0039 (16) |
C5 | 0.107 (5) | 0.049 (3) | 0.183 (11) | −0.017 (4) | 0.099 (5) | −0.009 (5) |
C5A | 0.016 (15) | 0.051 (14) | 0.025 (19) | 0.014 (9) | 0.009 (12) | 0.007 (7) |
C6 | 0.0665 (18) | 0.0479 (18) | 0.121 (2) | 0.0033 (15) | 0.0531 (18) | −0.0012 (16) |
C7 | 0.0504 (14) | 0.0312 (14) | 0.0606 (14) | 0.0006 (11) | 0.0190 (11) | −0.0040 (10) |
C8 | 0.0435 (13) | 0.0317 (13) | 0.0554 (13) | 0.0004 (11) | 0.0191 (10) | −0.0037 (10) |
C9 | 0.0483 (13) | 0.0283 (12) | 0.0460 (12) | −0.0005 (10) | 0.0146 (10) | −0.0028 (9) |
C10 | 0.0489 (13) | 0.0372 (15) | 0.0545 (13) | 0.0013 (11) | 0.0186 (11) | −0.0039 (11) |
C11 | 0.0438 (12) | 0.0324 (13) | 0.0478 (12) | 0.0004 (10) | 0.0154 (10) | −0.0032 (9) |
C12 | 0.0460 (13) | 0.0305 (13) | 0.0486 (12) | 0.0021 (10) | 0.0141 (10) | −0.0027 (9) |
C13 | 0.0480 (13) | 0.0398 (14) | 0.0480 (12) | 0.0020 (11) | 0.0172 (10) | −0.0021 (10) |
C14 | 0.0540 (14) | 0.0408 (14) | 0.0596 (14) | −0.0021 (12) | 0.0246 (12) | −0.0034 (11) |
C15 | 0.0670 (18) | 0.0568 (19) | 0.0710 (17) | 0.0090 (16) | 0.0313 (14) | −0.0027 (15) |
C16 | 0.0598 (18) | 0.091 (3) | 0.101 (2) | 0.0026 (18) | 0.0490 (17) | −0.0084 (18) |
C17 | 0.078 (2) | 0.074 (2) | 0.136 (3) | −0.0144 (19) | 0.068 (2) | −0.018 (2) |
C18 | 0.0652 (19) | 0.053 (2) | 0.085 (2) | 0.0109 (16) | 0.0283 (18) | −0.0111 (16) |
C19 | 0.0625 (16) | 0.0332 (14) | 0.0560 (15) | −0.0047 (12) | 0.0235 (13) | 0.0022 (11) |
C20 | 0.0640 (16) | 0.0357 (15) | 0.0581 (15) | −0.0077 (12) | 0.0272 (13) | −0.0036 (11) |
C21 | 0.0666 (18) | 0.0519 (19) | 0.0737 (18) | −0.0058 (15) | 0.0200 (15) | −0.0030 (15) |
C22 | 0.061 (2) | 0.091 (3) | 0.089 (2) | −0.010 (2) | 0.0107 (18) | −0.006 (2) |
Geometric parameters (Å, º) top
O1—C7 | 1.214 (2) | C5—C6 | 1.402 (12) |
O2—C14 | 1.358 (3) | C5—H5 | 0.94 (3) |
O2—C17 | 1.364 (3) | C5A—C6 | 1.34 (4) |
O3—C1 | 1.364 (3) | C5A—H5 | 0.94 (5) |
O3—C18 | 1.428 (3) | C6—H7 | 0.95 (3) |
N1—C7 | 1.341 (3) | C9—C11 | 1.413 (3) |
N1—C3 | 1.416 (3) | C10—C11 | 1.379 (3) |
N1—H15 | 0.89 (3) | C10—H3 | 0.98 (2) |
N2—C8 | 1.360 (3) | C11—C12 | 1.419 (3) |
N2—C7 | 1.411 (3) | C13—C14 | 1.450 (3) |
N2—H11 | 0.91 (2) | C14—C15 | 1.337 (3) |
N3—C8 | 1.295 (3) | C15—C16 | 1.414 (4) |
N3—C9 | 1.378 (3) | C15—H18 | 0.90 (2) |
N4—C9 | 1.336 (3) | C16—C17 | 1.322 (4) |
N4—N5 | 1.364 (2) | C16—H20 | 0.87 (3) |
N5—C10 | 1.340 (3) | C17—H21 | 1.03 (3) |
N5—C19 | 1.469 (3) | C18—H6 | 1.00 (3) |
N6—C12 | 1.326 (3) | C18—H10 | 0.99 (3) |
N6—C13 | 1.365 (3) | C18—H13 | 1.01 (4) |
N7—C13 | 1.331 (3) | C19—C20 | 1.506 (3) |
N7—N8 | 1.379 (2) | C19—H12 | 1.03 (3) |
N8—C12 | 1.373 (2) | C19—H19 | 0.99 (2) |
N8—C8 | 1.392 (2) | C20—C21 | 1.513 (4) |
C1—C6 | 1.362 (3) | C20—H1 | 1.00 (2) |
C1—C2 | 1.391 (3) | C20—H2 | 0.99 (2) |
C2—C3 | 1.366 (3) | C21—C22 | 1.512 (4) |
C2—H8 | 0.93 (2) | C21—H14 | 0.95 (3) |
C3—C4 | 1.377 (3) | C21—H17 | 1.00 (3) |
C4—C5 | 1.344 (10) | C22—H9 | 1.02 (3) |
C4—C5A | 1.54 (3) | C22—H16 | 1.00 (3) |
C4—H4 | 0.92 (3) | C22—H22 | 0.96 (3) |
| | | |
C14—O2—C17 | 106.3 (2) | N5—C10—C11 | 106.22 (19) |
C1—O3—C18 | 118.5 (2) | N5—C10—H3 | 123.3 (13) |
C7—N1—C3 | 127.3 (2) | C11—C10—H3 | 130.5 (13) |
C7—N1—H15 | 115.9 (17) | C10—C11—C9 | 104.80 (18) |
C3—N1—H15 | 116.6 (17) | C10—C11—C12 | 138.4 (2) |
C8—N2—C7 | 129.97 (19) | C9—C11—C12 | 116.80 (19) |
C8—N2—H11 | 117.6 (16) | N6—C12—N8 | 109.63 (18) |
C7—N2—H11 | 112.2 (16) | N6—C12—C11 | 135.7 (2) |
C8—N3—C9 | 116.30 (17) | N8—C12—C11 | 114.64 (18) |
C9—N4—N5 | 103.19 (16) | N7—C13—N6 | 116.77 (19) |
C10—N5—N4 | 113.87 (18) | N7—C13—C14 | 121.9 (2) |
C10—N5—C19 | 126.9 (2) | N6—C13—C14 | 121.34 (19) |
N4—N5—C19 | 119.27 (18) | C15—C14—O2 | 110.0 (2) |
C12—N6—C13 | 102.65 (17) | C15—C14—C13 | 133.5 (2) |
C13—N7—N8 | 100.69 (17) | O2—C14—C13 | 116.42 (19) |
C12—N8—N7 | 110.25 (16) | C14—C15—C16 | 106.5 (3) |
C12—N8—C8 | 125.33 (18) | C14—C15—H18 | 125.0 (15) |
N7—N8—C8 | 124.41 (18) | C16—C15—H18 | 128.4 (15) |
C6—C1—O3 | 124.5 (2) | C17—C16—C15 | 106.9 (3) |
C6—C1—C2 | 120.5 (2) | C17—C16—H20 | 123.7 (19) |
O3—C1—C2 | 115.0 (2) | C15—C16—H20 | 129.4 (19) |
C3—C2—C1 | 120.1 (2) | C16—C17—O2 | 110.2 (3) |
C3—C2—H8 | 121.5 (14) | C16—C17—H21 | 133.5 (19) |
C1—C2—H8 | 118.4 (14) | O2—C17—H21 | 116.3 (19) |
C2—C3—C4 | 119.9 (2) | O3—C18—H6 | 111.3 (17) |
C2—C3—N1 | 124.4 (2) | O3—C18—H10 | 109.2 (16) |
C4—C3—N1 | 115.7 (2) | H6—C18—H10 | 107 (2) |
C5—C4—C3 | 119.3 (4) | O3—C18—H13 | 105.9 (18) |
C5—C4—C5A | 16.7 (14) | H6—C18—H13 | 113 (2) |
C3—C4—C5A | 117.5 (14) | H10—C18—H13 | 111 (3) |
C5—C4—H4 | 122.8 (18) | N5—C19—C20 | 113.38 (19) |
C3—C4—H4 | 117.7 (17) | N5—C19—H12 | 105.3 (13) |
C5A—C4—H4 | 123 (2) | C20—C19—H12 | 109.3 (13) |
C4—C5—C6 | 122.0 (6) | N5—C19—H19 | 104.4 (13) |
C4—C5—H5 | 121 (2) | C20—C19—H19 | 111.2 (13) |
C6—C5—H5 | 115 (3) | H12—C19—H19 | 113.1 (18) |
C6—C5A—C4 | 113 (2) | C19—C20—C21 | 115.1 (2) |
C6—C5A—H5 | 121 (3) | C19—C20—H1 | 110.0 (12) |
C4—C5A—H5 | 105 (3) | C21—C20—H1 | 107.9 (12) |
C5A—C6—C1 | 121.5 (11) | C19—C20—H2 | 109.0 (12) |
C5A—C6—C5 | 19.2 (12) | C21—C20—H2 | 108.8 (12) |
C1—C6—C5 | 117.5 (5) | H1—C20—H2 | 105.7 (17) |
C5A—C6—H7 | 117 (2) | C22—C21—C20 | 112.3 (3) |
C1—C6—H7 | 118.4 (17) | C22—C21—H14 | 111.9 (16) |
C5—C6—H7 | 124.1 (17) | C20—C21—H14 | 107.6 (16) |
O1—C7—N1 | 127.5 (2) | C22—C21—H17 | 109.4 (15) |
O1—C7—N2 | 117.9 (2) | C20—C21—H17 | 110.6 (15) |
N1—C7—N2 | 114.6 (2) | H14—C21—H17 | 105 (2) |
N3—C8—N2 | 124.94 (19) | C21—C22—H9 | 110.1 (17) |
N3—C8—N8 | 121.3 (2) | C21—C22—H16 | 106.1 (19) |
N2—C8—N8 | 113.75 (18) | H9—C22—H16 | 105 (3) |
N4—C9—N3 | 122.49 (18) | C21—C22—H22 | 110.2 (19) |
N4—C9—C11 | 111.91 (19) | H9—C22—H22 | 108 (3) |
N3—C9—C11 | 125.59 (19) | H16—C22—H22 | 117 (3) |
(compound3)
N-[8-butyl-2-(2-furyl)-8
H-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 = 490.53 | F(000) = 1032 |
Triclinic, P1 | Dx = 1.336 Mg m−3 |
a = 12.6218 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.0932 (3) Å | Cell parameters from 15610 reflections |
c = 15.6948 (4) Å | θ = 2.0–27.0° |
α = 72.8670 (7)° | µ = 0.10 mm−1 |
β = 71.3280 (7)° | T = 295 K |
γ = 70.6350 (9)° | Prism, colourless |
V = 2439.16 (9) Å3 | 0.33 × 0.24 × 0.19 mm |
Data collection top
Nonius Kappa CCD diffractometer | 6467 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 27.0°, θmin = 2.0° |
ϕ scans and ω scans | h = −13→16 |
15610 measured reflections | k = −17→17 |
10558 independent reflections | l = −19→20 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.061 | H 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 reflections | Δρmax = 0.27 e Å−3 |
889 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.054 (5) |
Crystal data top
(C22H22N8O3)·0.5(C4H8O2) | γ = 70.6350 (9)° |
Mr = 490.53 | V = 2439.16 (9) Å3 |
Triclinic, P1 | Z = 4 |
a = 12.6218 (2) Å | Mo Kα radiation |
b = 14.0932 (3) Å | µ = 0.10 mm−1 |
c = 15.6948 (4) Å | T = 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 reflections | Rint = 0.024 |
10558 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.183 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.27 e Å−3 |
10558 reflections | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1A | 1.28893 (15) | 0.26617 (15) | −0.09746 (13) | 0.0801 (5) | |
O2A | 0.83391 (15) | 0.15403 (14) | 0.24399 (11) | 0.0783 (5) | |
O3A | 1.29417 (16) | 0.18973 (14) | −0.37575 (11) | 0.0766 (5) | |
N1A | 1.27861 (17) | 0.20955 (15) | −0.21577 (13) | 0.0633 (5) | |
N2A | 1.13523 (17) | 0.20846 (16) | −0.08019 (14) | 0.0652 (5) | |
N3A | 1.07998 (16) | 0.15832 (14) | −0.18595 (12) | 0.0595 (5) | |
N4A | 1.00524 (17) | 0.10412 (14) | −0.28009 (13) | 0.0649 (5) | |
N5A | 0.91157 (18) | 0.06644 (15) | −0.26095 (13) | 0.0659 (5) | |
N6A | 0.81605 (16) | 0.09127 (15) | 0.03984 (12) | 0.0637 (5) | |
N7A | 0.96959 (15) | 0.15020 (13) | −0.03305 (12) | 0.0563 (4) | |
N8A | 0.94590 (15) | 0.16261 (14) | 0.05526 (12) | 0.0603 (5) | |
C1A | 1.4751 (2) | 0.2423 (2) | −0.44474 (19) | 0.0768 (7) | |
C2A | 1.3835 (2) | 0.22130 (17) | −0.37188 (16) | 0.0633 (6) | |
C3A | 1.37741 (18) | 0.23070 (17) | −0.28404 (15) | 0.0592 (5) | |
C4A | 1.4644 (2) | 0.2586 (2) | −0.27045 (19) | 0.0694 (6) | |
C5A | 1.5568 (2) | 0.2793 (2) | −0.3441 (2) | 0.0797 (7) | |
C6A | 1.5616 (2) | 0.2712 (2) | −0.4298 (2) | 0.0828 (8) | |
C7A | 1.24083 (19) | 0.23127 (17) | −0.13209 (16) | 0.0601 (5) | |
C8A | 1.06366 (18) | 0.17239 (16) | −0.10458 (15) | 0.0560 (5) | |
C9A | 1.00097 (19) | 0.11965 (16) | −0.19892 (15) | 0.0570 (5) | |
C10A | 0.8514 (2) | 0.05770 (19) | −0.17312 (16) | 0.0669 (6) | |
C11A | 0.9056 (2) | 0.09250 (17) | −0.12981 (15) | 0.0588 (5) | |
C12A | 0.89075 (18) | 0.10777 (16) | −0.04093 (15) | 0.0566 (5) | |
C13A | 0.85326 (19) | 0.12591 (17) | 0.09490 (15) | 0.0588 (5) | |
C14A | 0.7926 (2) | 0.12113 (19) | 0.19094 (15) | 0.0646 (6) | |
C15A | 0.6993 (3) | 0.0874 (2) | 0.24127 (19) | 0.0844 (8) | |
C16A | 0.6803 (3) | 0.1005 (3) | 0.3317 (2) | 0.0943 (9) | |
C17A | 0.7622 (3) | 0.1399 (3) | 0.33005 (19) | 0.0890 (9) | |
C18A | 1.2889 (4) | 0.1795 (3) | −0.4606 (2) | 0.0944 (9) | |
C19A | 0.8914 (3) | 0.0366 (2) | −0.33535 (19) | 0.0781 (7) | |
C20A | 0.7725 (3) | 0.0201 (2) | −0.3120 (2) | 0.0757 (7) | |
C21A | 0.7471 (3) | −0.0041 (3) | −0.3900 (3) | 0.0960 (10) | |
C22A | 0.6300 (4) | −0.0260 (4) | −0.3629 (4) | 0.1158 (14) | |
O1B | 0.85787 (15) | 0.24873 (14) | −0.55214 (11) | 0.0771 (5) | |
O2B | 0.57986 (15) | 0.31651 (15) | −0.12631 (12) | 0.0829 (5) | |
O3B | 1.21344 (15) | 0.35088 (18) | −0.66246 (13) | 0.0947 (6) | |
N1B | 1.01712 (16) | 0.30987 (15) | −0.58938 (13) | 0.0605 (5) | |
N2B | 0.88489 (16) | 0.31312 (15) | −0.44787 (13) | 0.0599 (5) | |
N3B | 1.03549 (15) | 0.37727 (14) | −0.45036 (12) | 0.0574 (4) | |
N4B | 1.17808 (15) | 0.44127 (14) | −0.43220 (13) | 0.0601 (5) | |
N5B | 1.18979 (15) | 0.46648 (14) | −0.35848 (13) | 0.0591 (5) | |
N6B | 0.85096 (15) | 0.38809 (14) | −0.18119 (12) | 0.0604 (5) | |
N7B | 0.88282 (14) | 0.36002 (13) | −0.31875 (11) | 0.0528 (4) | |
N8B | 0.77962 (14) | 0.33578 (14) | −0.27164 (12) | 0.0571 (4) | |
C1B | 1.2444 (3) | 0.2883 (3) | −0.8021 (2) | 0.0897 (9) | |
C2B | 1.1810 (2) | 0.3098 (2) | −0.71638 (16) | 0.0704 (6) | |
C3B | 1.07312 (18) | 0.28892 (17) | −0.67781 (14) | 0.0585 (5) | |
C4B | 1.0305 (2) | 0.25047 (19) | −0.72733 (16) | 0.0656 (6) | |
C5B | 1.0945 (3) | 0.2300 (2) | −0.81245 (18) | 0.0801 (7) | |
C6B | 1.2014 (3) | 0.2480 (3) | −0.8489 (2) | 0.0918 (9) | |
C7B | 0.91880 (18) | 0.28774 (17) | −0.53427 (14) | 0.0573 (5) | |
C8B | 0.93964 (17) | 0.35111 (15) | −0.40910 (14) | 0.0525 (5) | |
C9B | 1.07977 (17) | 0.41167 (16) | −0.39875 (15) | 0.0545 (5) | |
C10B | 1.10419 (19) | 0.45399 (17) | −0.28249 (17) | 0.0604 (6) | |
C11B | 1.03001 (18) | 0.41875 (16) | −0.30628 (15) | 0.0556 (5) | |
C12B | 0.92377 (18) | 0.39100 (16) | −0.26342 (14) | 0.0541 (5) | |
C13B | 0.76576 (18) | 0.35480 (17) | −0.19028 (15) | 0.0567 (5) | |
C14B | 0.6663 (2) | 0.3447 (2) | −0.11459 (16) | 0.0663 (6) | |
C15B | 0.6222 (14) | 0.3839 (12) | −0.0354 (14) | 0.086 (4) | 0.50 |
C15C | 0.6528 (13) | 0.3418 (11) | −0.0266 (13) | 0.076 (3) | 0.50 |
C16B | 0.5166 (17) | 0.3651 (11) | 0.0087 (13) | 0.095 (4) | 0.50 |
C16C | 0.5422 (18) | 0.3172 (11) | 0.0183 (16) | 0.103 (5) | 0.50 |
C17B | 0.485 (3) | 0.331 (3) | −0.044 (3) | 0.091 (6) | 0.50 |
C17C | 0.509 (2) | 0.304 (3) | −0.047 (3) | 0.093 (7) | 0.50 |
C18B | 1.3233 (3) | 0.3724 (4) | −0.6945 (3) | 0.1020 (11) | |
C19B | 1.2914 (2) | 0.5024 (2) | −0.37002 (18) | 0.0659 (6) | |
C20B | 1.2907 (2) | 0.5286 (2) | −0.2837 (2) | 0.0694 (6) | |
C21B | 1.3957 (3) | 0.5645 (3) | −0.2930 (2) | 0.0898 (9) | |
C22B | 1.3902 (4) | 0.5925 (4) | −0.2052 (3) | 0.1091 (12) | |
O50 | 1.3901 (6) | 0.0278 (5) | 0.0551 (5) | 0.106 (2) | 0.50 |
O50A | 1.4158 (7) | −0.0344 (7) | 0.0750 (5) | 0.132 (3) | 0.50 |
C50 | 1.5102 (4) | −0.0104 (4) | −0.0876 (3) | 0.1274 (14) | |
C51 | 1.4092 (4) | −0.0192 (5) | −0.0135 (4) | 0.161 (2) | |
O60 | 1.0547 (4) | 0.4064 (3) | −0.0231 (4) | 0.1021 (17) | 0.60 |
O60A | 1.0613 (12) | 0.4510 (11) | −0.0734 (6) | 0.163 (5) | 0.40 |
C60A | 0.9371 (7) | 0.4840 (10) | −0.0501 (7) | 0.101 (3) | 0.40 |
C60 | 0.9325 (6) | 0.4312 (5) | 0.0293 (8) | 0.109 (2) | 0.60 |
C61 | 0.860 (3) | 0.515 (3) | 0.043 (2) | 0.203 (17) | 0.30 |
C61A | 0.8868 (5) | 0.5329 (6) | 0.0057 (8) | 0.121 (3) | 0.70 |
H1 | 0.820 (2) | 0.2994 (16) | −0.4108 (16) | 0.059 (6)* | |
H2 | 1.248 (3) | 0.230 (2) | −0.908 (2) | 0.099 (9)* | |
H3 | 0.634 (4) | −0.107 (3) | −0.308 (3) | 0.163 (16)* | |
H4 | 1.364 (2) | 0.4472 (18) | −0.3905 (17) | 0.073 (7)* | |
H5 | 1.319 (2) | 0.406 (2) | −0.649 (2) | 0.082 (9)* | |
H6 | 0.782 (3) | 0.162 (2) | 0.371 (2) | 0.104 (10)* | |
H7 | 1.109 (2) | 0.2257 (17) | −0.0288 (18) | 0.067 (7)* | |
H8 | 1.283 (3) | 0.244 (2) | −0.506 (2) | 0.114 (12)* | |
H9 | 1.103 (2) | 0.4677 (18) | −0.2259 (19) | 0.077 (7)* | |
H10 | 0.952 (3) | −0.029 (2) | −0.351 (2) | 0.095 (9)* | |
H11 | 1.222 (2) | 0.583 (2) | −0.2691 (18) | 0.080 (8)* | |
H12 | 1.313 (3) | 0.298 (2) | −0.816 (2) | 0.093 (9)* | |
H13 | 0.957 (2) | 0.2395 (18) | −0.7034 (19) | 0.080 (8)* | |
H14 | 1.478 (2) | 0.2307 (19) | −0.505 (2) | 0.086 (8)* | |
H15 | 0.903 (3) | 0.093 (2) | −0.391 (2) | 0.111 (10)* | |
H16 | 0.782 (2) | 0.0322 (18) | −0.1499 (17) | 0.074 (7)* | |
H18 | 1.403 (3) | 0.617 (3) | −0.347 (2) | 0.113 (11)* | |
H19 | 1.363 (3) | 0.125 (2) | −0.487 (2) | 0.112 (10)* | |
H20 | 1.047 (2) | 0.3401 (17) | −0.5662 (16) | 0.064 (7)* | |
H21 | 1.288 (2) | 0.469 (2) | −0.2359 (18) | 0.075 (7)* | |
H22 | 0.483 (4) | 0.352 (3) | 0.070 (3) | 0.154 (15)* | |
H23 | 1.619 (3) | 0.304 (2) | −0.330 (2) | 0.104 (9)* | |
H25 | 1.220 (3) | 0.153 (2) | −0.448 (2) | 0.100 (10)* | |
H26 | 1.627 (3) | 0.288 (2) | −0.481 (2) | 0.107 (9)* | |
H27 | 0.818 (3) | −0.066 (3) | −0.415 (2) | 0.124 (11)* | |
H28 | 0.619 (3) | 0.081 (2) | 0.387 (2) | 0.123 (11)* | |
H29 | 0.656 (3) | 0.063 (2) | 0.217 (2) | 0.105 (10)* | |
H30 | 1.2883 (19) | 0.5632 (18) | −0.4229 (17) | 0.069 (7)* | |
H31 | 0.716 (2) | 0.079 (2) | −0.2944 (19) | 0.086 (8)* | |
H32 | 0.678 (3) | 0.382 (3) | −0.008 (3) | 0.134 (14)* | |
H34 | 0.763 (2) | −0.043 (2) | −0.255 (2) | 0.091 (8)* | |
H35 | 1.231 (2) | 0.1896 (18) | −0.2318 (17) | 0.068 (7)* | |
H36 | 1.303 (4) | 0.646 (3) | −0.178 (3) | 0.169 (16)* | |
H37 | 1.064 (3) | 0.198 (2) | −0.844 (2) | 0.102 (10)* | |
H38 | 0.435 (3) | 0.297 (3) | −0.049 (2) | 0.120 (13)* | |
H39 | 0.610 (4) | −0.042 (3) | −0.409 (3) | 0.148 (14)* | |
H40 | 1.388 (3) | 0.295 (3) | −0.702 (2) | 0.119 (11)* | |
H41 | 1.448 (4) | 0.626 (3) | −0.215 (3) | 0.156 (15)* | |
H42 | 1.472 (4) | 0.505 (3) | −0.319 (3) | 0.150 (14)* | |
H43 | 1.328 (3) | 0.419 (2) | −0.750 (2) | 0.108 (11)* | |
H44 | 0.573 (3) | 0.023 (3) | −0.336 (3) | 0.122 (13)* | |
H45 | 1.400 (3) | 0.529 (3) | −0.158 (3) | 0.143 (16)* | |
H48 | 0.757 (3) | 0.046 (3) | −0.439 (3) | 0.132 (15)* | |
H51 | 1.463 (2) | 0.2659 (19) | −0.210 (2) | 0.087 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0636 (10) | 0.1176 (14) | 0.0770 (11) | −0.0392 (9) | −0.0016 (8) | −0.0463 (10) |
O2A | 0.0799 (11) | 0.1139 (13) | 0.0529 (9) | −0.0472 (10) | −0.0024 (8) | −0.0249 (9) |
O3A | 0.0827 (12) | 0.0999 (12) | 0.0569 (10) | −0.0395 (9) | −0.0071 (8) | −0.0242 (8) |
N1A | 0.0574 (11) | 0.0837 (13) | 0.0536 (11) | −0.0328 (10) | −0.0011 (9) | −0.0190 (9) |
N2A | 0.0599 (11) | 0.0922 (14) | 0.0525 (11) | −0.0349 (10) | 0.0034 (9) | −0.0301 (10) |
N3A | 0.0613 (11) | 0.0681 (11) | 0.0519 (11) | −0.0277 (9) | −0.0025 (8) | −0.0173 (8) |
N4A | 0.0751 (13) | 0.0694 (11) | 0.0547 (11) | −0.0302 (9) | −0.0060 (9) | −0.0175 (9) |
N5A | 0.0810 (13) | 0.0721 (12) | 0.0532 (11) | −0.0327 (10) | −0.0117 (9) | −0.0166 (9) |
N6A | 0.0645 (11) | 0.0817 (12) | 0.0508 (10) | −0.0348 (9) | −0.0030 (9) | −0.0169 (9) |
N7A | 0.0559 (10) | 0.0696 (11) | 0.0471 (10) | −0.0260 (8) | −0.0038 (8) | −0.0169 (8) |
N8A | 0.0591 (11) | 0.0771 (12) | 0.0475 (10) | −0.0270 (9) | −0.0017 (8) | −0.0194 (8) |
C1A | 0.0737 (17) | 0.0878 (17) | 0.0579 (15) | −0.0252 (13) | 0.0028 (12) | −0.0157 (13) |
C2A | 0.0580 (13) | 0.0683 (13) | 0.0585 (14) | −0.0197 (10) | −0.0040 (10) | −0.0139 (10) |
C3A | 0.0508 (12) | 0.0671 (13) | 0.0541 (13) | −0.0187 (10) | −0.0020 (9) | −0.0128 (10) |
C4A | 0.0560 (14) | 0.0880 (17) | 0.0649 (16) | −0.0261 (12) | −0.0074 (11) | −0.0171 (13) |
C5A | 0.0549 (14) | 0.0969 (19) | 0.0811 (19) | −0.0279 (13) | −0.0017 (13) | −0.0171 (14) |
C6A | 0.0579 (15) | 0.0975 (19) | 0.0767 (19) | −0.0273 (13) | 0.0074 (13) | −0.0129 (14) |
C7A | 0.0529 (12) | 0.0699 (13) | 0.0582 (13) | −0.0206 (10) | −0.0028 (10) | −0.0212 (11) |
C8A | 0.0537 (12) | 0.0618 (12) | 0.0520 (12) | −0.0219 (9) | −0.0013 (9) | −0.0166 (9) |
C9A | 0.0621 (13) | 0.0583 (12) | 0.0516 (12) | −0.0209 (10) | −0.0066 (10) | −0.0151 (9) |
C10A | 0.0769 (16) | 0.0784 (15) | 0.0536 (13) | −0.0360 (13) | −0.0088 (12) | −0.0160 (11) |
C11A | 0.0643 (13) | 0.0661 (13) | 0.0506 (12) | −0.0286 (10) | −0.0064 (10) | −0.0143 (10) |
C12A | 0.0565 (12) | 0.0634 (12) | 0.0533 (12) | −0.0260 (10) | −0.0064 (10) | −0.0133 (9) |
C13A | 0.0587 (13) | 0.0697 (13) | 0.0510 (12) | −0.0255 (10) | −0.0068 (10) | −0.0146 (10) |
C14A | 0.0633 (14) | 0.0845 (15) | 0.0515 (13) | −0.0325 (12) | −0.0033 (10) | −0.0193 (11) |
C15A | 0.0842 (19) | 0.115 (2) | 0.0645 (16) | −0.0549 (17) | 0.0062 (14) | −0.0291 (15) |
C16A | 0.101 (2) | 0.125 (2) | 0.0589 (16) | −0.0586 (19) | 0.0124 (15) | −0.0254 (15) |
C17A | 0.099 (2) | 0.125 (2) | 0.0508 (15) | −0.0506 (19) | 0.0020 (14) | −0.0289 (15) |
C18A | 0.100 (2) | 0.123 (3) | 0.074 (2) | −0.030 (2) | −0.0173 (18) | −0.043 (2) |
C19A | 0.109 (2) | 0.0799 (18) | 0.0597 (15) | −0.0383 (16) | −0.0186 (15) | −0.0219 (14) |
C20A | 0.0894 (19) | 0.0740 (16) | 0.0759 (18) | −0.0179 (14) | −0.0328 (15) | −0.0237 (14) |
C21A | 0.120 (3) | 0.098 (2) | 0.089 (2) | −0.018 (2) | −0.044 (2) | −0.039 (2) |
C22A | 0.119 (3) | 0.126 (3) | 0.143 (4) | −0.017 (2) | −0.066 (3) | −0.067 (3) |
O1B | 0.0685 (10) | 0.1187 (13) | 0.0632 (10) | −0.0503 (10) | −0.0013 (8) | −0.0339 (9) |
O2B | 0.0667 (11) | 0.1342 (15) | 0.0636 (11) | −0.0537 (10) | 0.0023 (9) | −0.0327 (10) |
O3B | 0.0652 (11) | 0.1592 (18) | 0.0675 (11) | −0.0609 (12) | −0.0012 (9) | −0.0159 (11) |
N1B | 0.0531 (11) | 0.0847 (13) | 0.0494 (10) | −0.0301 (9) | −0.0034 (8) | −0.0187 (9) |
N2B | 0.0503 (10) | 0.0886 (13) | 0.0491 (10) | −0.0339 (9) | −0.0010 (8) | −0.0211 (9) |
N3B | 0.0500 (10) | 0.0751 (11) | 0.0513 (10) | −0.0266 (8) | −0.0052 (8) | −0.0157 (8) |
N4B | 0.0504 (10) | 0.0743 (11) | 0.0596 (11) | −0.0260 (8) | −0.0092 (8) | −0.0139 (9) |
N5B | 0.0498 (10) | 0.0704 (11) | 0.0631 (11) | −0.0255 (8) | −0.0116 (8) | −0.0140 (9) |
N6B | 0.0554 (10) | 0.0809 (12) | 0.0511 (10) | −0.0296 (9) | −0.0057 (8) | −0.0178 (9) |
N7B | 0.0457 (9) | 0.0695 (10) | 0.0475 (9) | −0.0254 (8) | −0.0036 (7) | −0.0157 (8) |
N8B | 0.0485 (10) | 0.0757 (11) | 0.0506 (10) | −0.0280 (8) | −0.0016 (8) | −0.0167 (8) |
C1B | 0.0616 (17) | 0.125 (2) | 0.0634 (17) | −0.0294 (16) | 0.0067 (13) | −0.0112 (16) |
C2B | 0.0589 (14) | 0.0985 (17) | 0.0509 (13) | −0.0278 (12) | −0.0094 (11) | −0.0076 (12) |
C3B | 0.0525 (12) | 0.0708 (13) | 0.0442 (11) | −0.0167 (10) | −0.0041 (9) | −0.0087 (10) |
C4B | 0.0663 (15) | 0.0773 (15) | 0.0510 (13) | −0.0208 (12) | −0.0075 (11) | −0.0160 (11) |
C5B | 0.095 (2) | 0.0883 (18) | 0.0524 (14) | −0.0255 (15) | −0.0071 (14) | −0.0187 (13) |
C6B | 0.094 (2) | 0.114 (2) | 0.0533 (16) | −0.0215 (17) | 0.0019 (15) | −0.0248 (15) |
C7B | 0.0505 (12) | 0.0763 (13) | 0.0483 (12) | −0.0254 (10) | −0.0048 (9) | −0.0160 (10) |
C8B | 0.0478 (11) | 0.0645 (12) | 0.0466 (11) | −0.0192 (9) | −0.0064 (9) | −0.0146 (9) |
C9B | 0.0462 (11) | 0.0614 (12) | 0.0557 (12) | −0.0198 (9) | −0.0067 (9) | −0.0119 (9) |
C10B | 0.0544 (13) | 0.0740 (14) | 0.0590 (14) | −0.0263 (10) | −0.0107 (11) | −0.0158 (11) |
C11B | 0.0503 (12) | 0.0668 (12) | 0.0542 (12) | −0.0236 (9) | −0.0086 (9) | −0.0145 (10) |
C12B | 0.0502 (11) | 0.0656 (12) | 0.0500 (12) | −0.0222 (9) | −0.0089 (9) | −0.0134 (9) |
C13B | 0.0517 (12) | 0.0735 (13) | 0.0497 (12) | −0.0266 (10) | −0.0061 (9) | −0.0151 (10) |
C14B | 0.0575 (13) | 0.0978 (17) | 0.0533 (13) | −0.0379 (12) | −0.0023 (10) | −0.0224 (12) |
C15B | 0.066 (8) | 0.143 (12) | 0.065 (5) | −0.045 (7) | 0.003 (5) | −0.046 (8) |
C15C | 0.055 (6) | 0.126 (10) | 0.060 (5) | −0.039 (5) | 0.004 (4) | −0.039 (7) |
C16B | 0.088 (9) | 0.154 (12) | 0.058 (5) | −0.066 (9) | 0.022 (5) | −0.048 (8) |
C16C | 0.078 (8) | 0.159 (13) | 0.080 (7) | −0.062 (9) | 0.025 (6) | −0.052 (10) |
C17B | 0.059 (10) | 0.148 (15) | 0.070 (7) | −0.046 (9) | 0.017 (7) | −0.040 (9) |
C17C | 0.059 (11) | 0.17 (2) | 0.075 (6) | −0.066 (13) | 0.020 (8) | −0.056 (11) |
C18B | 0.072 (2) | 0.135 (3) | 0.098 (3) | −0.057 (2) | −0.0121 (18) | −0.001 (3) |
C19B | 0.0538 (14) | 0.0766 (15) | 0.0748 (16) | −0.0319 (12) | −0.0153 (12) | −0.0108 (13) |
C20B | 0.0572 (15) | 0.0782 (17) | 0.0818 (18) | −0.0298 (13) | −0.0145 (13) | −0.0189 (14) |
C21B | 0.079 (2) | 0.127 (3) | 0.087 (2) | −0.0608 (19) | −0.0094 (16) | −0.032 (2) |
C22B | 0.094 (3) | 0.162 (4) | 0.108 (3) | −0.073 (3) | −0.016 (2) | −0.044 (3) |
O50 | 0.075 (3) | 0.136 (5) | 0.094 (5) | −0.029 (3) | 0.003 (3) | −0.029 (4) |
O50A | 0.127 (6) | 0.192 (7) | 0.096 (4) | −0.113 (6) | −0.026 (4) | 0.020 (5) |
C50 | 0.104 (3) | 0.202 (4) | 0.098 (3) | −0.070 (3) | −0.011 (2) | −0.045 (3) |
C51 | 0.129 (4) | 0.274 (6) | 0.129 (4) | −0.115 (4) | −0.010 (3) | −0.066 (4) |
O60 | 0.072 (3) | 0.090 (3) | 0.169 (5) | −0.0003 (19) | −0.030 (3) | −0.087 (3) |
O60A | 0.147 (8) | 0.276 (15) | 0.107 (7) | −0.071 (9) | −0.008 (6) | −0.112 (8) |
C60A | 0.061 (5) | 0.170 (9) | 0.105 (7) | −0.022 (5) | −0.021 (5) | −0.086 (7) |
C60 | 0.085 (4) | 0.095 (4) | 0.161 (7) | −0.028 (3) | −0.038 (4) | −0.033 (4) |
C61 | 0.23 (3) | 0.32 (4) | 0.148 (16) | −0.21 (3) | 0.075 (17) | −0.16 (2) |
C61A | 0.051 (3) | 0.127 (5) | 0.212 (10) | −0.011 (3) | −0.014 (4) | −0.108 (6) |
Geometric parameters (Å, º) top
O1A—C7A | 1.214 (3) | N7B—C12B | 1.368 (3) |
O2A—C14A | 1.359 (3) | N7B—N8B | 1.375 (2) |
O2A—C17A | 1.365 (3) | N7B—C8B | 1.391 (3) |
O3A—C2A | 1.366 (3) | N8B—C13B | 1.327 (3) |
O3A—C18A | 1.406 (3) | C1B—C6B | 1.365 (5) |
N1A—C7A | 1.336 (3) | C1B—C2B | 1.390 (4) |
N1A—C3A | 1.412 (3) | C1B—H12 | 0.87 (3) |
N1A—H35 | 0.87 (3) | C2B—C3B | 1.392 (3) |
N2A—C8A | 1.364 (3) | C3B—C4B | 1.377 (3) |
N2A—C7A | 1.406 (3) | C4B—C5B | 1.379 (3) |
N2A—H7 | 0.84 (3) | C4B—H13 | 0.93 (3) |
N3A—C8A | 1.291 (3) | C5B—C6B | 1.364 (4) |
N3A—C9A | 1.374 (3) | C5B—H37 | 0.98 (3) |
N4A—C9A | 1.337 (3) | C6B—H2 | 0.98 (3) |
N4A—N5A | 1.366 (3) | C9B—C11B | 1.404 (3) |
N5A—C10A | 1.336 (3) | C10B—C11B | 1.380 (3) |
N5A—C19A | 1.468 (3) | C10B—H9 | 0.96 (3) |
N6A—C12A | 1.325 (3) | C11B—C12B | 1.421 (3) |
N6A—C13A | 1.366 (3) | C13B—C14B | 1.439 (3) |
N7A—C12A | 1.371 (3) | C14B—C15C | 1.325 (19) |
N7A—N8A | 1.373 (2) | C14B—C15B | 1.384 (18) |
N7A—C8A | 1.398 (3) | C15B—C15C | 0.59 (2) |
N8A—C13A | 1.329 (3) | C15B—C16B | 1.36 (3) |
C1A—C2A | 1.383 (3) | C15B—C16C | 1.49 (3) |
C1A—C6A | 1.388 (4) | C15B—H32 | 0.92 (4) |
C1A—H14 | 1.00 (3) | C15C—C16C | 1.45 (3) |
C2A—C3A | 1.399 (3) | C15C—C16B | 1.58 (2) |
C3A—C4A | 1.375 (3) | C15C—H32 | 0.88 (4) |
C4A—C5A | 1.395 (3) | C16B—C16C | 0.64 (2) |
C4A—H51 | 0.98 (3) | C16B—C17B | 1.29 (5) |
C5A—C6A | 1.363 (4) | C16B—C17C | 1.44 (4) |
C5A—H23 | 1.06 (3) | C16B—H22 | 0.91 (5) |
C6A—H26 | 0.99 (3) | C16C—C17C | 1.31 (5) |
C9A—C11A | 1.413 (3) | C16C—C17B | 1.33 (5) |
C10A—C11A | 1.373 (3) | C16C—H22 | 1.03 (5) |
C10A—H16 | 0.98 (3) | C17B—H38 | 0.94 (5) |
C11A—C12A | 1.418 (3) | C17C—H38 | 0.97 (6) |
C13A—C14A | 1.448 (3) | C18B—H5 | 0.95 (3) |
C14A—C15A | 1.339 (3) | C18B—H40 | 1.14 (3) |
C15A—C16A | 1.419 (4) | C18B—H43 | 0.92 (3) |
C15A—H29 | 0.95 (3) | C19B—C20B | 1.502 (4) |
C16A—C17A | 1.316 (4) | C19B—H4 | 1.02 (2) |
C16A—H28 | 1.00 (4) | C19B—H30 | 1.00 (2) |
C17A—H6 | 0.93 (3) | C20B—C21B | 1.520 (3) |
C18A—H8 | 0.97 (3) | C20B—H11 | 0.96 (3) |
C18A—H19 | 1.06 (4) | C20B—H21 | 0.95 (3) |
C18A—H25 | 0.99 (3) | C21B—C22B | 1.516 (5) |
C19A—C20A | 1.506 (4) | C21B—H18 | 0.95 (3) |
C19A—H10 | 1.02 (3) | C21B—H42 | 1.10 (4) |
C19A—H15 | 1.00 (3) | C22B—H36 | 1.14 (5) |
C20A—C21A | 1.512 (4) | C22B—H41 | 0.95 (5) |
C20A—H31 | 0.94 (3) | C22B—H45 | 0.97 (4) |
C20A—H34 | 1.07 (3) | O50—O50A | 0.828 (8) |
C21A—C22A | 1.512 (6) | O50—C51 | 1.342 (9) |
C21A—H27 | 1.08 (4) | O50—C50i | 1.428 (8) |
C21A—H48 | 0.89 (4) | O50A—C51 | 1.367 (9) |
C22A—H3 | 1.21 (4) | O50A—C50i | 1.376 (8) |
C22A—H39 | 0.93 (4) | C50—O50Ai | 1.376 (8) |
C22A—H44 | 0.90 (4) | C50—O50i | 1.428 (8) |
O1B—C7B | 1.217 (3) | C50—C51 | 1.437 (6) |
O2B—C17C | 1.29 (4) | O60—O60A | 0.852 (11) |
O2B—C14B | 1.357 (3) | O60—C61Aii | 1.427 (10) |
O2B—C17B | 1.47 (3) | O60—C60 | 1.476 (9) |
O3B—C2B | 1.374 (3) | O60—C60A | 1.623 (12) |
O3B—C18B | 1.418 (3) | O60—C61ii | 1.69 (3) |
N1B—C7B | 1.340 (3) | O60A—C60A | 1.435 (15) |
N1B—C3B | 1.410 (3) | O60A—C61ii | 1.48 (3) |
N1B—H20 | 0.86 (2) | O60A—C61Aii | 1.514 (14) |
N2B—C8B | 1.357 (3) | O60A—C60 | 1.917 (14) |
N2B—C7B | 1.401 (3) | C60A—C61A | 1.164 (11) |
N2B—H1 | 0.88 (2) | C60A—C60 | 1.244 (11) |
N3B—C8B | 1.293 (2) | C60A—C61 | 1.56 (2) |
N3B—C9B | 1.380 (3) | C60—C61 | 1.26 (4) |
N4B—C9B | 1.337 (3) | C60—C61A | 1.341 (11) |
N4B—N5B | 1.369 (3) | C61—C61A | 0.60 (3) |
N5B—C10B | 1.341 (3) | C61—O60Aii | 1.48 (3) |
N5B—C19B | 1.471 (3) | C61—O60ii | 1.69 (3) |
N6B—C12B | 1.322 (3) | C61A—O60ii | 1.427 (9) |
N6B—C13B | 1.367 (3) | C61A—O60Aii | 1.514 (14) |
| | | |
C14A—O2A—C17A | 105.9 (2) | C15C—C15B—C16B | 100 (4) |
C2A—O3A—C18A | 119.4 (2) | C15C—C15B—C14B | 72 (3) |
C7A—N1A—C3A | 126.6 (2) | C16B—C15B—C14B | 109.3 (16) |
C7A—N1A—H35 | 115.0 (17) | C15C—C15B—C16C | 75 (4) |
C3A—N1A—H35 | 117.6 (17) | C16B—C15B—C16C | 25.4 (11) |
C8A—N2A—C7A | 129.4 (2) | C14B—C15B—C16C | 98.9 (14) |
C8A—N2A—H7 | 115.0 (16) | C15C—C15B—H32 | 67 (4) |
C7A—N2A—H7 | 115.2 (16) | C16B—C15B—H32 | 127 (3) |
C8A—N3A—C9A | 116.88 (18) | C14B—C15B—H32 | 114 (3) |
C9A—N4A—N5A | 103.09 (17) | C16C—C15B—H32 | 116 (3) |
C10A—N5A—N4A | 113.87 (19) | C15B—C15C—C14B | 83 (4) |
C10A—N5A—C19A | 127.9 (2) | C15B—C15C—C16C | 82 (4) |
N4A—N5A—C19A | 118.2 (2) | C14B—C15C—C16C | 103.8 (16) |
C12A—N6A—C13A | 102.87 (17) | C15B—C15C—C16B | 58 (3) |
C12A—N7A—N8A | 110.43 (16) | C14B—C15C—C16B | 100.7 (13) |
C12A—N7A—C8A | 123.98 (18) | C16C—C15C—C16B | 23.9 (9) |
N8A—N7A—C8A | 125.52 (17) | C15B—C15C—H32 | 74 (4) |
C13A—N8A—N7A | 100.98 (17) | C14B—C15C—H32 | 123 (3) |
C2A—C1A—C6A | 119.6 (3) | C16C—C15C—H32 | 123 (3) |
C2A—C1A—H14 | 116.8 (16) | C16B—C15C—H32 | 109 (3) |
C6A—C1A—H14 | 123.5 (16) | C16C—C16B—C17B | 80 (4) |
O3A—C2A—C1A | 126.1 (2) | C16C—C16B—C15B | 89 (4) |
O3A—C2A—C3A | 113.88 (19) | C17B—C16B—C15B | 109 (2) |
C1A—C2A—C3A | 120.1 (2) | C16C—C16B—C17C | 65 (4) |
C4A—C3A—C2A | 119.5 (2) | C17B—C16B—C17C | 16 (3) |
C4A—C3A—N1A | 125.7 (2) | C15B—C16B—C17C | 101.6 (19) |
C2A—C3A—N1A | 114.9 (2) | C16C—C16B—C15C | 67 (3) |
C3A—C4A—C5A | 120.2 (3) | C17B—C16B—C15C | 105.2 (17) |
C3A—C4A—H51 | 121.6 (16) | C15B—C16B—C15C | 21.8 (11) |
C5A—C4A—H51 | 118.2 (16) | C17C—C16B—C15C | 93.2 (16) |
C6A—C5A—C4A | 120.0 (3) | C16C—C16B—H22 | 81 (4) |
C6A—C5A—H23 | 123.1 (17) | C17B—C16B—H22 | 118 (4) |
C4A—C5A—H23 | 116.8 (17) | C15B—C16B—H22 | 129 (3) |
C5A—C6A—C1A | 120.6 (2) | C17C—C16B—H22 | 118 (3) |
C5A—C6A—H26 | 118.4 (18) | C15C—C16B—H22 | 120 (3) |
C1A—C6A—H26 | 120.9 (18) | C16B—C16C—C17C | 89 (5) |
O1A—C7A—N1A | 126.8 (2) | C16B—C16C—C17B | 72 (4) |
O1A—C7A—N2A | 118.5 (2) | C17C—C16C—C17B | 18 (3) |
N1A—C7A—N2A | 114.8 (2) | C16B—C16C—C15C | 89 (4) |
N3A—C8A—N2A | 124.04 (19) | C17C—C16C—C15C | 105 (2) |
N3A—C8A—N7A | 121.70 (19) | C17B—C16C—C15C | 110 (2) |
N2A—C8A—N7A | 114.26 (19) | C16B—C16C—C15B | 66 (3) |
N4A—C9A—N3A | 123.30 (19) | C17C—C16C—C15B | 102 (2) |
N4A—C9A—C11A | 111.71 (19) | C17B—C16C—C15B | 100 (2) |
N3A—C9A—C11A | 125.0 (2) | C15C—C16C—C15B | 23.2 (8) |
N5A—C10A—C11A | 106.4 (2) | C16B—C16C—H22 | 61 (4) |
N5A—C10A—H16 | 122.6 (15) | C17C—C16C—H22 | 121 (3) |
C11A—C10A—H16 | 131.0 (15) | C17B—C16C—H22 | 106 (3) |
C10A—C11A—C9A | 105.0 (2) | C15C—C16C—H22 | 122 (3) |
C10A—C11A—C12A | 138.3 (2) | C15B—C16C—H22 | 108 (3) |
C9A—C11A—C12A | 116.76 (19) | C16B—C17B—C16C | 28.3 (14) |
N6A—C12A—N7A | 109.37 (19) | C16B—C17B—O2B | 108 (3) |
N6A—C12A—C11A | 135.0 (2) | C16C—C17B—O2B | 101 (2) |
N7A—C12A—C11A | 115.59 (18) | C16B—C17B—H38 | 147 (5) |
N8A—C13A—N6A | 116.35 (19) | C16C—C17B—H38 | 134 (5) |
N8A—C13A—C14A | 123.6 (2) | O2B—C17B—H38 | 102 (4) |
N6A—C13A—C14A | 120.02 (19) | O2B—C17C—C16C | 113 (2) |
C15A—C14A—O2A | 110.3 (2) | O2B—C17C—C16B | 110 (2) |
C15A—C14A—C13A | 131.4 (2) | C16C—C17C—C16B | 26.3 (12) |
O2A—C14A—C13A | 118.26 (19) | O2B—C17C—H38 | 114 (4) |
C14A—C15A—C16A | 106.2 (3) | C16C—C17C—H38 | 132 (4) |
C14A—C15A—H29 | 124 (2) | C16B—C17C—H38 | 123 (3) |
C16A—C15A—H29 | 129.5 (19) | O3B—C18B—H5 | 100.4 (18) |
C17A—C16A—C15A | 106.8 (3) | O3B—C18B—H40 | 104.8 (17) |
C17A—C16A—H28 | 126.4 (19) | H5—C18B—H40 | 121 (2) |
C15A—C16A—H28 | 126.7 (19) | O3B—C18B—H43 | 111 (2) |
C16A—C17A—O2A | 110.8 (3) | H5—C18B—H43 | 108 (3) |
C16A—C17A—H6 | 137 (2) | H40—C18B—H43 | 111 (3) |
O2A—C17A—H6 | 112 (2) | N5B—C19B—C20B | 111.9 (2) |
O3A—C18A—H8 | 113 (2) | N5B—C19B—H4 | 108.3 (13) |
O3A—C18A—H19 | 110.1 (18) | C20B—C19B—H4 | 111.7 (14) |
H8—C18A—H19 | 108 (3) | N5B—C19B—H30 | 105.1 (13) |
O3A—C18A—H25 | 106.3 (18) | C20B—C19B—H30 | 112.6 (13) |
H8—C18A—H25 | 110 (3) | H4—C19B—H30 | 106.8 (19) |
H19—C18A—H25 | 108 (2) | C19B—C20B—C21B | 113.2 (2) |
N5A—C19A—C20A | 112.5 (2) | C19B—C20B—H11 | 108.1 (16) |
N5A—C19A—H10 | 110.6 (16) | C21B—C20B—H11 | 108.5 (15) |
C20A—C19A—H10 | 108.9 (16) | C19B—C20B—H21 | 108.0 (15) |
N5A—C19A—H15 | 106.0 (18) | C21B—C20B—H21 | 109.3 (15) |
C20A—C19A—H15 | 111.6 (18) | H11—C20B—H21 | 110 (2) |
H10—C19A—H15 | 107 (2) | C22B—C21B—C20B | 111.5 (3) |
C19A—C20A—C21A | 113.4 (3) | C22B—C21B—H18 | 116 (2) |
C19A—C20A—H31 | 109.5 (16) | C20B—C21B—H18 | 108 (2) |
C21A—C20A—H31 | 109.6 (17) | C22B—C21B—H42 | 117 (2) |
C19A—C20A—H34 | 110.5 (15) | C20B—C21B—H42 | 106 (2) |
C21A—C20A—H34 | 106.4 (15) | H18—C21B—H42 | 97 (3) |
H31—C20A—H34 | 107 (2) | C21B—C22B—H36 | 112 (2) |
C20A—C21A—C22A | 112.2 (3) | C21B—C22B—H41 | 111 (3) |
C20A—C21A—H27 | 108.7 (18) | H36—C22B—H41 | 107 (3) |
C22A—C21A—H27 | 113.5 (18) | C21B—C22B—H45 | 108 (2) |
C20A—C21A—H48 | 109 (2) | H36—C22B—H45 | 107 (3) |
C22A—C21A—H48 | 114 (3) | H41—C22B—H45 | 111 (3) |
H27—C21A—H48 | 99 (3) | O50A—O50—C51 | 73.9 (10) |
C21A—C22A—H3 | 108 (2) | O50A—O50—C50i | 69.4 (9) |
C21A—C22A—H39 | 116 (3) | C51—O50—C50i | 114.5 (5) |
H3—C22A—H39 | 99 (3) | O50—O50A—C51 | 70.6 (9) |
C21A—C22A—H44 | 112 (2) | O50—O50A—C50i | 76.3 (10) |
H3—C22A—H44 | 108 (3) | C51—O50A—C50i | 116.3 (5) |
H39—C22A—H44 | 112 (3) | O50Ai—C50—O50i | 34.3 (3) |
C17C—O2B—C14B | 106.4 (16) | O50Ai—C50—C51 | 116.0 (5) |
C17C—O2B—C17B | 15 (3) | O50i—C50—C51 | 112.0 (4) |
C14B—O2B—C17B | 105.5 (17) | O50—C51—O50A | 35.6 (4) |
C2B—O3B—C18B | 118.4 (3) | O50—C51—C50 | 116.8 (5) |
C7B—N1B—C3B | 127.0 (2) | O50A—C51—C50 | 119.4 (5) |
C7B—N1B—H20 | 113.9 (16) | O60A—O60—C61Aii | 78.9 (11) |
C3B—N1B—H20 | 119.1 (16) | O60A—O60—C60 | 107.9 (12) |
C8B—N2B—C7B | 129.99 (18) | C61Aii—O60—C60 | 108.6 (6) |
C8B—N2B—H1 | 113.4 (15) | O60A—O60—C60A | 61.9 (11) |
C7B—N2B—H1 | 116.5 (15) | C61Aii—O60—C60A | 107.1 (5) |
C8B—N3B—C9B | 116.14 (18) | C60—O60—C60A | 47.0 (4) |
C9B—N4B—N5B | 103.05 (17) | O60A—O60—C61ii | 61.3 (18) |
C10B—N5B—N4B | 113.87 (17) | C61Aii—O60—C61ii | 20.0 (11) |
C10B—N5B—C19B | 127.8 (2) | C60—O60—C61ii | 121.3 (10) |
N4B—N5B—C19B | 118.37 (18) | C60A—O60—C61ii | 103.6 (17) |
C12B—N6B—C13B | 102.85 (17) | O60—O60A—C60A | 86.5 (13) |
C12B—N7B—N8B | 110.53 (16) | O60—O60A—C61ii | 88.4 (19) |
C12B—N7B—C8B | 124.68 (17) | C60A—O60A—C61ii | 126.3 (14) |
N8B—N7B—C8B | 124.76 (17) | O60—O60A—C61Aii | 67.6 (10) |
C13B—N8B—N7B | 100.76 (16) | C60A—O60A—C61Aii | 112.7 (7) |
C6B—C1B—C2B | 120.6 (3) | C61ii—O60A—C61Aii | 23.0 (12) |
C6B—C1B—H12 | 128 (2) | O60—O60A—C60 | 47.1 (9) |
C2B—C1B—H12 | 111 (2) | C60A—O60A—C60 | 40.4 (5) |
O3B—C2B—C1B | 126.6 (2) | C61ii—O60A—C60 | 107.8 (11) |
O3B—C2B—C3B | 113.9 (2) | C61Aii—O60A—C60 | 86.0 (6) |
C1B—C2B—C3B | 119.5 (3) | C61A—C60A—C60 | 67.6 (7) |
C4B—C3B—C2B | 118.8 (2) | C61A—C60A—O60A | 121.0 (8) |
C4B—C3B—N1B | 125.8 (2) | C60—C60A—O60A | 91.1 (9) |
C2B—C3B—N1B | 115.4 (2) | C61A—C60A—C61 | 19.0 (15) |
C3B—C4B—C5B | 120.9 (3) | C60—C60A—C61 | 51.7 (17) |
C3B—C4B—H13 | 119.3 (17) | O60A—C60A—C61 | 124.8 (15) |
C5B—C4B—H13 | 119.7 (17) | C61A—C60A—O60 | 109.2 (8) |
C6B—C5B—C4B | 120.1 (3) | C60—C60A—O60 | 60.3 (7) |
C6B—C5B—H37 | 121.0 (19) | O60A—C60A—O60 | 31.6 (5) |
C4B—C5B—H37 | 118.8 (19) | C61—C60A—O60 | 103.4 (18) |
C1B—C6B—C5B | 120.1 (3) | C60A—C60—C61 | 77.4 (17) |
C1B—C6B—H2 | 120.6 (17) | C60A—C60—C61A | 53.4 (6) |
C5B—C6B—H2 | 119.2 (17) | C61—C60—C61A | 26.4 (14) |
O1B—C7B—N1B | 126.6 (2) | C60A—C60—O60 | 72.7 (7) |
O1B—C7B—N2B | 118.19 (18) | C61—C60—O60 | 132.2 (14) |
N1B—C7B—N2B | 115.18 (19) | C61A—C60—O60 | 108.5 (7) |
N3B—C8B—N2B | 124.54 (19) | C60A—C60—O60A | 48.4 (6) |
N3B—C8B—N7B | 121.84 (19) | C61—C60—O60A | 112.0 (15) |
N2B—C8B—N7B | 113.61 (17) | C61A—C60—O60A | 86.2 (7) |
N4B—C9B—N3B | 122.82 (19) | O60—C60—O60A | 25.0 (5) |
N4B—C9B—C11B | 111.92 (19) | C61A—C61—C60 | 85 (4) |
N3B—C9B—C11B | 125.26 (18) | C61A—C61—O60Aii | 82 (3) |
N5B—C10B—C11B | 105.8 (2) | C60—C61—O60Aii | 94 (3) |
N5B—C10B—H9 | 121.9 (15) | C61A—C61—C60A | 39 (3) |
C11B—C10B—H9 | 132.3 (15) | C60—C61—C60A | 50.9 (10) |
C10B—C11B—C9B | 105.39 (19) | O60Aii—C61—C60A | 102.9 (16) |
C10B—C11B—C12B | 137.4 (2) | C61A—C61—O60ii | 55 (3) |
C9B—C11B—C12B | 117.17 (19) | C60—C61—O60ii | 102.9 (19) |
N6B—C12B—N7B | 109.42 (17) | O60Aii—C61—O60ii | 30.3 (6) |
N6B—C12B—C11B | 135.8 (2) | C60A—C61—O60ii | 86.2 (12) |
N7B—C12B—C11B | 114.81 (18) | C61—C61A—C60A | 122 (4) |
N8B—C13B—N6B | 116.44 (18) | C61—C61A—C60 | 69 (4) |
N8B—C13B—C14B | 123.57 (19) | C60A—C61A—C60 | 59.0 (7) |
N6B—C13B—C14B | 120.0 (2) | C61—C61A—O60ii | 105 (3) |
C15C—C14B—O2B | 111.0 (8) | C60A—C61A—O60ii | 117.8 (8) |
C15C—C14B—C15B | 25.2 (9) | C60—C61A—O60ii | 113.7 (6) |
O2B—C14B—C15B | 106.8 (8) | C61—C61A—O60Aii | 75 (3) |
C15C—C14B—C13B | 128.7 (8) | C60A—C61A—O60Aii | 125.1 (7) |
O2B—C14B—C13B | 119.2 (2) | C60—C61A—O60Aii | 89.2 (8) |
C15B—C14B—C13B | 131.6 (9) | O60ii—C61A—O60Aii | 33.5 (5) |
Symmetry codes: (i) −x+3, −y, −z; (ii) −x+2, −y+1, −z. |
(compound4)
N-[8-methyl-2-(2-furyl)-9-(methylthio)-8
H-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 = 468.50 | F(000) = 488 |
Triclinic, P1 | Dx = 1.415 Mg m−3 |
a = 10.1490 (3) Å | Mo Kα radiation, λ = 0.71070 Å |
b = 10.5112 (3) Å | Cell parameters from 10025 reflections |
c = 11.4025 (4) Å | θ = 1–30° |
α = 110.1850 (18)° | µ = 0.19 mm−1 |
β = 97.9640 (18)° | T = 295 K |
γ = 99.6510 (13)° | Plate, colourless |
V = 1099.89 (6) Å3 | 0.50 × 0.28 × 0.05 mm |
Data collection top
Nonius Kappa CCD diffractometer | 2970 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 27.0°, θmin = 3.0° |
ϕ scans and ω scans | h = −12→12 |
10025 measured reflections | k = −13→13 |
4777 independent reflections | l = −14→14 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.196 | H 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 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Crystal data top
(C20H18N8SO3)·(H2O) | γ = 99.6510 (13)° |
Mr = 468.50 | V = 1099.89 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.1490 (3) Å | Mo Kα radiation |
b = 10.5112 (3) Å | µ = 0.19 mm−1 |
c = 11.4025 (4) Å | T = 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 reflections | Rint = 0.028 |
4777 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.196 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.53 e Å−3 |
4777 reflections | Δρmin = −0.24 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.66826 (10) | 0.04211 (9) | 0.38306 (9) | 0.0774 (3) | |
O1 | 0.3748 (3) | 0.7107 (3) | 0.1458 (3) | 0.0864 (7) | |
O2 | 0.1061 (2) | 0.4036 (2) | 0.5111 (2) | 0.0718 (6) | |
O3 | 0.8379 (3) | 0.9353 (3) | −0.1316 (2) | 0.0914 (8) | |
N1 | 0.5817 (3) | 0.6532 (3) | 0.1381 (3) | 0.0695 (7) | |
N2 | 0.4267 (3) | 0.5614 (3) | 0.2363 (3) | 0.0689 (7) | |
N3 | 0.6061 (3) | 0.4456 (2) | 0.2253 (2) | 0.0638 (6) | |
N4 | 0.7690 (3) | 0.3068 (3) | 0.2198 (2) | 0.0665 (7) | |
N5 | 0.7822 (3) | 0.2050 (3) | 0.2661 (2) | 0.0633 (6) | |
N6 | 0.3971 (2) | 0.2532 (2) | 0.4294 (2) | 0.0626 (6) | |
N7 | 0.4320 (2) | 0.3995 (2) | 0.3308 (2) | 0.0589 (6) | |
N8 | 0.3162 (2) | 0.4221 (2) | 0.3767 (2) | 0.0612 (6) | |
C1 | 0.8270 (4) | 0.7764 (4) | −0.0297 (3) | 0.0742 (9) | |
C2 | 0.7633 (4) | 0.7074 (3) | 0.0369 (3) | 0.0708 (9) | |
C3 | 0.6407 (3) | 0.7304 (3) | 0.0706 (3) | 0.0621 (8) | |
C4 | 0.5816 (4) | 0.8257 (3) | 0.0362 (3) | 0.0687 (8) | |
C5 | 0.6464 (4) | 0.8966 (3) | −0.0313 (3) | 0.0686 (9) | |
C6 | 0.7682 (4) | 0.8721 (3) | −0.0646 (3) | 0.0683 (8) | |
C7 | 0.4597 (4) | 0.6480 (3) | 0.1692 (3) | 0.0680 (8) | |
C8 | 0.4946 (3) | 0.4683 (3) | 0.2618 (3) | 0.0622 (7) | |
C9 | 0.6578 (3) | 0.3447 (3) | 0.2557 (3) | 0.0598 (7) | |
C10 | 0.6825 (3) | 0.1776 (3) | 0.3275 (3) | 0.0594 (7) | |
C11 | 0.5993 (3) | 0.2680 (3) | 0.3226 (3) | 0.0572 (7) | |
C12 | 0.4791 (3) | 0.2978 (3) | 0.3637 (3) | 0.0581 (7) | |
C13 | 0.3012 (3) | 0.3318 (3) | 0.4342 (3) | 0.0596 (7) | |
C14 | 0.1937 (3) | 0.3163 (3) | 0.5018 (3) | 0.0635 (8) | |
C15 | 0.1615 (4) | 0.2332 (4) | 0.5650 (4) | 0.0830 (10) | |
C16 | 0.0497 (4) | 0.2703 (5) | 0.6177 (4) | 0.0889 (11) | |
C17 | 0.0194 (4) | 0.3718 (4) | 0.5836 (4) | 0.0818 (10) | |
C18 | 0.8984 (4) | 0.1414 (4) | 0.2455 (4) | 0.0774 (10) | |
C19 | 0.7894 (6) | 1.0435 (5) | −0.1578 (5) | 0.0941 (12) | |
C20 | 0.6584 (5) | 0.1330 (5) | 0.5462 (4) | 0.0823 (10) | |
H1 | 0.358 (3) | 0.561 (3) | 0.259 (3) | 0.050 (9)* | |
H2 | 0.628 (4) | 0.604 (4) | 0.154 (4) | 0.093 (13)* | |
H3 | 0.199 (4) | 0.158 (4) | 0.562 (4) | 0.106 (13)* | |
H4 | 0.012 (4) | 0.232 (4) | 0.668 (4) | 0.095 (12)* | |
H5 | −0.054 (4) | 0.423 (4) | 0.596 (3) | 0.089 (11)* | |
H6 | 0.987 (5) | 0.210 (5) | 0.261 (4) | 0.113 (15)* | |
H7 | 0.922 (6) | 0.102 (6) | 0.313 (6) | 0.17 (2)* | |
H8 | 0.899 (5) | 0.083 (5) | 0.155 (5) | 0.139 (17)* | |
H9 | 0.493 (4) | 0.842 (3) | 0.062 (3) | 0.075 (10)* | |
H10 | 0.602 (3) | 0.960 (4) | −0.058 (3) | 0.082 (10)* | |
H11 | 0.909 (4) | 0.758 (4) | −0.050 (3) | 0.086 (11)* | |
H12 | 0.800 (3) | 0.649 (3) | 0.066 (3) | 0.079 (10)* | |
H13 | 0.785 (5) | 1.123 (5) | −0.074 (5) | 0.123 (16)* | |
H14 | 0.856 (4) | 1.071 (4) | −0.203 (4) | 0.101 (13)* | |
H15 | 0.697 (5) | 1.012 (5) | −0.209 (4) | 0.117 (16)* | |
H16 | 0.739 (5) | 0.215 (4) | 0.590 (4) | 0.102 (13)* | |
H17 | 0.574 (5) | 0.164 (5) | 0.544 (4) | 0.121 (15)* | |
H18 | 0.647 (5) | 0.058 (5) | 0.587 (5) | 0.142 (17)* | |
O1A | 0.1086 (5) | 0.5967 (5) | −0.0467 (5) | 0.0851 (13) | 0.50 |
O2A | 0.1332 (7) | 0.5957 (9) | 0.1852 (7) | 0.143 (3) | 0.50 |
H1A | 0.1311 | 0.6235 | −0.1146 | 0.12 (3)* | 0.50 |
H1B | 0.1768 | 0.6192 | 0.0160 | 0.10 (3)* | 0.50 |
H2A | 0.0601 | 0.5036 | 0.1503 | 0.050* | 0.50 |
H2B | 0.0935 | 0.6266 | 0.1357 | 0.050* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0945 (7) | 0.0691 (5) | 0.0858 (6) | 0.0371 (5) | 0.0209 (5) | 0.0413 (4) |
O1 | 0.0879 (17) | 0.0813 (15) | 0.1128 (18) | 0.0414 (13) | 0.0195 (14) | 0.0548 (14) |
O2 | 0.0646 (13) | 0.0661 (12) | 0.0954 (15) | 0.0231 (11) | 0.0219 (11) | 0.0380 (11) |
O3 | 0.116 (2) | 0.0966 (17) | 0.1016 (18) | 0.0498 (16) | 0.0423 (15) | 0.0667 (15) |
N1 | 0.0785 (19) | 0.0616 (15) | 0.0837 (18) | 0.0307 (14) | 0.0148 (14) | 0.0404 (14) |
N2 | 0.0722 (19) | 0.0596 (15) | 0.0884 (19) | 0.0265 (14) | 0.0215 (16) | 0.0375 (14) |
N3 | 0.0707 (17) | 0.0551 (14) | 0.0719 (15) | 0.0218 (12) | 0.0149 (13) | 0.0284 (12) |
N4 | 0.0716 (17) | 0.0637 (15) | 0.0689 (15) | 0.0234 (13) | 0.0125 (12) | 0.0280 (12) |
N5 | 0.0689 (16) | 0.0623 (14) | 0.0612 (14) | 0.0266 (12) | 0.0088 (12) | 0.0228 (12) |
N6 | 0.0521 (14) | 0.0600 (14) | 0.0777 (16) | 0.0138 (11) | 0.0045 (12) | 0.0317 (12) |
N7 | 0.0614 (15) | 0.0480 (12) | 0.0676 (14) | 0.0166 (11) | 0.0080 (11) | 0.0227 (11) |
N8 | 0.0585 (15) | 0.0544 (13) | 0.0693 (14) | 0.0181 (11) | 0.0075 (11) | 0.0218 (11) |
C1 | 0.092 (3) | 0.074 (2) | 0.078 (2) | 0.0409 (19) | 0.0264 (18) | 0.0401 (17) |
C2 | 0.089 (2) | 0.0655 (18) | 0.0747 (19) | 0.0408 (17) | 0.0172 (17) | 0.0361 (16) |
C3 | 0.080 (2) | 0.0492 (15) | 0.0585 (16) | 0.0186 (14) | 0.0041 (14) | 0.0242 (13) |
C4 | 0.080 (2) | 0.0614 (17) | 0.0727 (19) | 0.0289 (16) | 0.0088 (16) | 0.0322 (15) |
C5 | 0.088 (2) | 0.0581 (17) | 0.0663 (18) | 0.0269 (16) | 0.0035 (16) | 0.0316 (14) |
C6 | 0.091 (2) | 0.0619 (17) | 0.0597 (16) | 0.0280 (17) | 0.0126 (16) | 0.0288 (14) |
C7 | 0.081 (2) | 0.0546 (16) | 0.0711 (18) | 0.0245 (16) | 0.0086 (16) | 0.0259 (14) |
C8 | 0.075 (2) | 0.0450 (14) | 0.0651 (17) | 0.0164 (14) | 0.0050 (14) | 0.0215 (13) |
C9 | 0.0645 (18) | 0.0520 (15) | 0.0608 (16) | 0.0173 (14) | 0.0056 (13) | 0.0199 (13) |
C10 | 0.0638 (18) | 0.0572 (16) | 0.0591 (16) | 0.0212 (14) | 0.0097 (13) | 0.0220 (13) |
C11 | 0.0578 (17) | 0.0504 (15) | 0.0623 (16) | 0.0154 (13) | 0.0046 (13) | 0.0220 (12) |
C12 | 0.0577 (17) | 0.0483 (14) | 0.0656 (16) | 0.0113 (13) | −0.0001 (13) | 0.0236 (13) |
C13 | 0.0536 (16) | 0.0504 (15) | 0.0704 (17) | 0.0101 (13) | −0.0005 (13) | 0.0237 (13) |
C14 | 0.0486 (16) | 0.0622 (17) | 0.0802 (19) | 0.0136 (13) | 0.0036 (14) | 0.0311 (15) |
C15 | 0.064 (2) | 0.091 (3) | 0.116 (3) | 0.0243 (19) | 0.0134 (19) | 0.066 (2) |
C16 | 0.072 (2) | 0.103 (3) | 0.116 (3) | 0.022 (2) | 0.028 (2) | 0.067 (3) |
C17 | 0.067 (2) | 0.084 (2) | 0.107 (3) | 0.0202 (19) | 0.027 (2) | 0.046 (2) |
C18 | 0.074 (2) | 0.089 (2) | 0.076 (2) | 0.043 (2) | 0.0164 (18) | 0.029 (2) |
C19 | 0.119 (4) | 0.086 (3) | 0.103 (3) | 0.032 (3) | 0.022 (3) | 0.064 (3) |
C20 | 0.076 (2) | 0.105 (3) | 0.078 (2) | 0.026 (2) | 0.0157 (19) | 0.047 (2) |
O1A | 0.085 (3) | 0.081 (3) | 0.097 (3) | 0.014 (3) | 0.023 (3) | 0.045 (3) |
O2A | 0.110 (5) | 0.187 (7) | 0.123 (5) | 0.056 (5) | 0.036 (4) | 0.033 (5) |
Geometric parameters (Å, º) top
S1—C10 | 1.741 (3) | C2—H12 | 0.90 (3) |
S1—C20 | 1.800 (4) | C3—C4 | 1.387 (4) |
O1—C7 | 1.223 (4) | C4—C5 | 1.397 (5) |
O2—C17 | 1.364 (4) | C4—H9 | 1.01 (4) |
O2—C14 | 1.370 (4) | C5—C6 | 1.382 (5) |
O3—C6 | 1.366 (4) | C5—H10 | 0.97 (4) |
O3—C19 | 1.417 (4) | C9—C11 | 1.405 (4) |
N1—C7 | 1.332 (5) | C10—C11 | 1.383 (4) |
N1—C3 | 1.416 (4) | C11—C12 | 1.411 (4) |
N1—H2 | 0.80 (4) | C13—C14 | 1.439 (4) |
N2—C8 | 1.372 (4) | C14—C15 | 1.339 (5) |
N2—C7 | 1.405 (4) | C15—C16 | 1.406 (6) |
N2—H1 | 0.77 (3) | C15—H3 | 0.93 (4) |
N3—C8 | 1.290 (4) | C16—C17 | 1.321 (5) |
N3—C9 | 1.383 (3) | C16—H4 | 0.90 (4) |
N4—C9 | 1.329 (4) | C17—H5 | 0.99 (4) |
N4—N5 | 1.364 (3) | C18—H6 | 1.01 (5) |
N5—C10 | 1.354 (4) | C18—H7 | 1.01 (6) |
N5—C18 | 1.457 (4) | C18—H8 | 1.00 (5) |
N6—C12 | 1.326 (4) | C19—H13 | 1.04 (5) |
N6—C13 | 1.373 (4) | C19—H14 | 0.97 (4) |
N7—N8 | 1.374 (3) | C19—H15 | 0.97 (5) |
N7—C12 | 1.382 (3) | C20—H16 | 1.00 (4) |
N7—C8 | 1.388 (4) | C20—H17 | 0.97 (5) |
N8—C13 | 1.329 (4) | C20—H18 | 1.04 (5) |
C1—C2 | 1.371 (5) | O1A—H1A | 0.953 (5) |
C1—C6 | 1.392 (4) | O1A—H1B | 0.859 (6) |
C1—H11 | 0.93 (4) | O2A—H2A | 1.029 (8) |
C2—C3 | 1.387 (5) | O2A—H2B | 0.833 (8) |
| | | |
C10—S1—C20 | 100.75 (18) | N3—C9—C11 | 125.3 (3) |
C17—O2—C14 | 105.9 (3) | N5—C10—C11 | 105.6 (2) |
C6—O3—C19 | 117.7 (3) | N5—C10—S1 | 122.3 (2) |
C7—N1—C3 | 128.0 (3) | C11—C10—S1 | 131.9 (2) |
C7—N1—H2 | 119 (3) | C10—C11—C9 | 105.1 (3) |
C3—N1—H2 | 113 (3) | C10—C11—C12 | 137.5 (3) |
C8—N2—C7 | 129.4 (3) | C9—C11—C12 | 117.4 (2) |
C8—N2—H1 | 113 (2) | N6—C12—N7 | 109.2 (3) |
C7—N2—H1 | 117 (2) | N6—C12—C11 | 135.9 (3) |
C8—N3—C9 | 115.8 (3) | N7—C12—C11 | 114.9 (3) |
C9—N4—N5 | 103.4 (3) | N8—C13—N6 | 116.4 (3) |
C10—N5—N4 | 113.5 (2) | N8—C13—C14 | 123.5 (3) |
C10—N5—C18 | 128.6 (3) | N6—C13—C14 | 120.1 (3) |
N4—N5—C18 | 117.9 (3) | C15—C14—O2 | 109.7 (3) |
C12—N6—C13 | 102.9 (2) | C15—C14—C13 | 132.5 (3) |
N8—N7—C12 | 110.4 (2) | O2—C14—C13 | 117.8 (3) |
N8—N7—C8 | 125.6 (2) | C14—C15—C16 | 106.7 (3) |
C12—N7—C8 | 124.0 (3) | C14—C15—H3 | 125 (3) |
C13—N8—N7 | 101.1 (2) | C16—C15—H3 | 128 (3) |
C2—C1—C6 | 119.7 (4) | C17—C16—C15 | 107.2 (4) |
C2—C1—H11 | 119 (2) | C17—C16—H4 | 129 (3) |
C6—C1—H11 | 121 (2) | C15—C16—H4 | 124 (3) |
C1—C2—C3 | 121.5 (3) | C16—C17—O2 | 110.4 (4) |
C1—C2—H12 | 123 (2) | C16—C17—H5 | 133 (2) |
C3—C2—H12 | 116 (2) | O2—C17—H5 | 116 (2) |
C2—C3—C4 | 119.1 (3) | N5—C18—H6 | 114 (2) |
C2—C3—N1 | 117.5 (3) | N5—C18—H7 | 110 (3) |
C4—C3—N1 | 123.4 (3) | H6—C18—H7 | 100 (4) |
C3—C4—C5 | 119.6 (3) | N5—C18—H8 | 117 (3) |
C3—C4—H9 | 118.0 (19) | H6—C18—H8 | 96 (4) |
C5—C4—H9 | 122.4 (19) | H7—C18—H8 | 117 (4) |
C6—C5—C4 | 120.6 (3) | O3—C19—H13 | 111 (3) |
C6—C5—H10 | 120 (2) | O3—C19—H14 | 102 (3) |
C4—C5—H10 | 119 (2) | H13—C19—H14 | 114 (3) |
O3—C6—C5 | 124.7 (3) | O3—C19—H15 | 112 (3) |
O3—C6—C1 | 115.8 (3) | H13—C19—H15 | 105 (4) |
C5—C6—C1 | 119.5 (3) | H14—C19—H15 | 112 (4) |
O1—C7—N1 | 126.8 (3) | S1—C20—H16 | 110 (2) |
O1—C7—N2 | 117.3 (3) | S1—C20—H17 | 107 (3) |
N1—C7—N2 | 115.9 (3) | H16—C20—H17 | 110 (4) |
N3—C8—N2 | 123.7 (3) | S1—C20—H18 | 106 (3) |
N3—C8—N7 | 122.5 (3) | H16—C20—H18 | 116 (3) |
N2—C8—N7 | 113.8 (3) | H17—C20—H18 | 107 (4) |
N4—C9—N3 | 122.3 (3) | H1A—O1A—H1B | 113.4 (5) |
N4—C9—C11 | 112.4 (3) | H2A—O2A—H2B | 92.7 (7) |
Experimental details
| (compound1) | (compound2) | (compound3) | (compound4) |
Crystal data |
Chemical formula | (C18H13O2N8Cl)·0.5(H2O) | C22H22N8O3 | (C22H22N8O3)·0.5(C4H8O2) | (C20H18N8SO3)·(H2O) |
Mr | 417.82 | 446.48 | 490.53 | 468.50 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/c | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 295 | 295 | 295 | 295 |
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), 90 | 72.8670 (7), 71.3280 (7), 70.6350 (9) | 110.1850 (18), 97.9640 (18), 99.6510 (13) |
V (Å3) | 1887.81 (6) | 2153.81 (10) | 2439.16 (9) | 1099.89 (6) |
Z | 4 | 4 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.24 | 0.10 | 0.10 | 0.19 |
Crystal size (mm) | 0.50 × 0.38 × 0.12 | 0.51 × 0.19 × 0.07 | 0.33 × 0.24 × 0.19 | 0.50 × 0.28 × 0.05 |
|
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 | 14447, 8951, 6646 | 9542, 5159, 2594 | 15610, 10558, 6467 | 10025, 4777, 2970 |
Rint | 0.022 | 0.057 | 0.024 | 0.028 |
(sin θ/λ)max (Å−1) | 0.661 | 0.661 | 0.639 | 0.639 |
|
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 reflections | 8951 | 5159 | 10558 | 4777 |
No. of parameters | 644 | 396 | 889 | 381 |
H-atom treatment | All H-atom parameters refined | All H-atom parameters refined | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.39 | 0.19, −0.24 | 0.27, −0.20 | 0.53, −0.24 |