Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020454/hk2233sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020454/hk2233Isup2.hkl |
CCDC reference: 651370
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.098
- wR factor = 0.184
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C SHFSU01_ALERT_2_C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.096 Additional refinement cycles may be required. PLAT080_ALERT_2_C Maximum Shift/Error ............................ 0.10 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 2000 Deg. PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general backgroud, see: Allen et al. (1987); Sanghhvi et al. (1989); Tenser et al. (2001); Nizamuddin-Mishra et al. (2001); Perreux & Loupy (2001). For related literature, see: Bazgir et al. (2006a,b).
6-Amino-1,3-dimethyluracil (310 mg, 2 mmol), 4-fluorobenzaldehyde (124 mg, 1 mmol) and montmorillonite K10 (400 mg) were mixed together. The reaction mixture was placed in a screw-capped vial and irradiated for 5 min with microwave irradiation (700 W). After cooling, the reaction mixture was washed with ethanol and then recrystallized from ethyl acetate to afford the pure product (yield; 210 mg, 53%, m.p. 543–545 K).
H atoms were positioned geometrically with C—H = 0.93 and 0.96 Å, for aromatic and methyl H atoms, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Pyridopyrimidines are annelated uracils that have attracted considerable interest in recent years. Their derivatives have been known to display a wide range of pharmacological activities, such as antitumor (Sanghhvi et al., 1989), antiviral (Tenser et al., 2001) and antifungal (Nizamuddin-Mishra et al., 2001). Therefore, for the preparation of these complex molecules large efforts have been directed towards the synthetic manipulation of uracils. As a result, a number of reports have appeared in the literature that usually describe forcing conditions, long reaction times and complex synthetic pathways. Thus, new routes for the synthesis of these molecules have attracted considerable attention allowing for a rapid entry to these heterocycles. Microwave-assisted organic synthesis is an increasingly popular field as indicated by numerous publications in the past few years owing to several advantages, such as enhanced reaction rates and increase in yields under milder conditions (Perreux & Loupy, 2001). In light of the above, we have synthesized the title compound, (I), under microwave-assisted conditions and characterized its structure.
In the molecule of (I), (Fig. 1), the bond lengths and angles are generally within normal ranges (Allen et al., 1987) and may be compared with the corresponding ones in similar structures (Bazgir et al., 2006a,b). The asymmetric unit contains two independent molecules.
Rings A (N1/N2/C87C9/C11), B (N3/C7/C8/C13/C14/C19), C (N4/N5/C14/C16/C187C19) D (C1—C6) and A' (N6/N7/C27/C28/C30/C32), B' (N8/C26/C27/C32/C33/C38), C' (N9/N10/C33/C35/C37/C38), D' (C20—C25) are, of course, planar and the dihedral angles between them are A/B = 2.62 (2), A/C = 5.08 (3), B/C = 2.48 (2) and A'/B' = 7.58 (2), A'/C' = 12.28 (3), B'/C' = 4.92 (3)°.
The weak π-π stacking interactions, involving the adjacent rings with centroid-centroid distance of 3.507 (4) %A [symmetry code: x, y + 1/2, z] may be effective in the stabilization of the crystal structure.
For general backgroud, see: Allen et al. (1987); Sanghhvi et al. (1989); Tenser et al. (2001); Nizamuddin-Mishra et al. (2001); Perreux & Loupy (2001). For related literature, see: Bazgir et al. (2006a,b).
Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C19H16FN5O4 | Z = 4 |
Mr = 397.37 | F(000) = 824 |
Triclinic, P1 | Dx = 1.469 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.074 (2) Å | Cell parameters from 2000 reflections |
b = 10.930 (3) Å | θ = 2.0–28.0° |
c = 20.091 (5) Å | µ = 0.11 mm−1 |
α = 75.04 (2)° | T = 294 K |
β = 76.82 (2)° | Plate, colorless |
γ = 70.93 (2)° | 0.25 × 0.25 × 0.04 mm |
V = 1796.8 (8) Å3 |
Stoe IPDSII diffractometer | 5359 reflections with I > 2σ(I) |
rotation method scans | Rint = 0.050 |
Absorption correction: numerical shape of crystal determined optically (X-RED32 and X-SHAPE; Stoe & Cie, 2005) | θmax = 28.0°, θmin = 2.0° |
Tmin = 0.950, Tmax = 0.995 | h = −11→11 |
15435 measured reflections | k = −12→14 |
8540 independent reflections | l = −26→26 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.098 | w = 1/[σ2(Fo2) + (0.0373P)2 + 1.6536P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.184 | (Δ/σ)max = 0.096 |
S = 1.23 | Δρmax = 0.19 e Å−3 |
8540 reflections | Δρmin = −0.24 e Å−3 |
531 parameters |
C19H16FN5O4 | γ = 70.93 (2)° |
Mr = 397.37 | V = 1796.8 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.074 (2) Å | Mo Kα radiation |
b = 10.930 (3) Å | µ = 0.11 mm−1 |
c = 20.091 (5) Å | T = 294 K |
α = 75.04 (2)° | 0.25 × 0.25 × 0.04 mm |
β = 76.82 (2)° |
Stoe IPDSII diffractometer | 8540 independent reflections |
Absorption correction: numerical shape of crystal determined optically (X-RED32 and X-SHAPE; Stoe & Cie, 2005) | 5359 reflections with I > 2σ(I) |
Tmin = 0.950, Tmax = 0.995 | Rint = 0.050 |
15435 measured reflections |
R[F2 > 2σ(F2)] = 0.098 | 0 restraints |
wR(F2) = 0.184 | H-atom parameters constrained |
S = 1.23 | Δρmax = 0.19 e Å−3 |
8540 reflections | Δρmin = −0.24 e Å−3 |
531 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.4778 (5) | 0.2016 (4) | 0.2535 (2) | 0.0503 (9) | |
C2 | 0.3908 (5) | 0.2376 (4) | 0.2011 (2) | 0.0587 (11) | |
H2 | 0.3021 | 0.3107 | 0.1995 | 0.07* | |
C3 | 0.4381 (5) | 0.1625 (4) | 0.1504 (2) | 0.0546 (10) | |
H3 | 0.3818 | 0.1858 | 0.1135 | 0.066* | |
C4 | 0.5682 (4) | 0.0530 (3) | 0.15386 (17) | 0.0393 (8) | |
C5 | 0.6521 (4) | 0.0174 (4) | 0.20864 (18) | 0.0442 (8) | |
H5 | 0.7394 | −0.0568 | 0.2113 | 0.053* | |
C6 | 0.6056 (5) | 0.0925 (4) | 0.25931 (19) | 0.0499 (9) | |
H6 | 0.6603 | 0.0695 | 0.2967 | 0.06* | |
C7 | 0.6216 (4) | −0.0241 (3) | 0.09701 (17) | 0.0410 (8) | |
C8 | 0.7181 (4) | 0.0176 (3) | 0.03454 (17) | 0.0417 (8) | |
C9 | 0.7701 (5) | 0.1376 (4) | 0.0207 (2) | 0.0496 (9) | |
C10 | 0.9087 (6) | 0.2890 (4) | −0.0633 (2) | 0.0691 (12) | |
H10A | 0.9199 | 0.3093 | −0.0213 | 0.083* | |
H10B | 0.8312 | 0.361 | −0.086 | 0.083* | |
H10C | 1.0081 | 0.2754 | −0.0939 | 0.083* | |
C11 | 0.9018 (5) | 0.0935 (4) | −0.0969 (2) | 0.0552 (10) | |
C12 | 0.9192 (6) | −0.1058 (5) | −0.1321 (2) | 0.0713 (13) | |
H12A | 0.8463 | −0.0781 | −0.1646 | 0.086* | |
H12B | 0.9293 | −0.1965 | −0.1099 | 0.086* | |
H12C | 1.0204 | −0.0966 | −0.1563 | 0.086* | |
C13 | 0.7668 (4) | −0.0605 (4) | −0.01636 (18) | 0.0441 (8) | |
C14 | 0.6372 (4) | −0.2105 (4) | 0.05081 (19) | 0.0443 (8) | |
C15 | 0.6760 (7) | −0.4117 (4) | 0.0055 (2) | 0.0777 (15) | |
H15A | 0.7724 | −0.3925 | −0.0191 | 0.093* | |
H15B | 0.606 | −0.3957 | −0.0272 | 0.093* | |
H15C | 0.6988 | −0.5026 | 0.029 | 0.093* | |
C16 | 0.4980 (6) | −0.3747 (4) | 0.1134 (2) | 0.0607 (11) | |
C17 | 0.3346 (6) | −0.3582 (5) | 0.2271 (2) | 0.0679 (12) | |
H17A | 0.2261 | −0.3153 | 0.2217 | 0.081* | |
H17B | 0.3538 | −0.3429 | 0.2689 | 0.081* | |
H17C | 0.3568 | −0.4514 | 0.2302 | 0.081* | |
C18 | 0.4697 (5) | −0.1872 (4) | 0.1662 (2) | 0.0490 (9) | |
C19 | 0.5773 (4) | −0.1397 (3) | 0.10484 (18) | 0.0428 (8) | |
C20 | 0.1273 (5) | 0.5408 (5) | 0.7954 (2) | 0.0605 (11) | |
C21 | 0.0886 (6) | 0.4813 (5) | 0.7527 (2) | 0.0639 (11) | |
H21 | 0.0456 | 0.4108 | 0.7709 | 0.077* | |
C22 | 0.1154 (4) | 0.5295 (4) | 0.6808 (2) | 0.0479 (9) | |
H22 | 0.0903 | 0.4904 | 0.6505 | 0.057* | |
C23 | 0.1790 (4) | 0.6346 (3) | 0.65424 (17) | 0.0362 (7) | |
C24 | 0.2156 (4) | 0.6923 (4) | 0.69921 (19) | 0.0467 (9) | |
H24 | 0.2581 | 0.7632 | 0.6816 | 0.056* | |
C25 | 0.1894 (5) | 0.6452 (4) | 0.7709 (2) | 0.0572 (10) | |
H25 | 0.2136 | 0.684 | 0.8015 | 0.069* | |
C26 | 0.2175 (4) | 0.6864 (3) | 0.57664 (17) | 0.0356 (7) | |
C27 | 0.3742 (4) | 0.6615 (3) | 0.54272 (17) | 0.0364 (7) | |
C28 | 0.5081 (4) | 0.5747 (3) | 0.57779 (18) | 0.0389 (8) | |
C29 | 0.7927 (4) | 0.5130 (4) | 0.5778 (2) | 0.0572 (10) | |
H29A | 0.7922 | 0.4226 | 0.5952 | 0.069* | |
H29B | 0.7857 | 0.5533 | 0.616 | 0.069* | |
H29C | 0.8888 | 0.5162 | 0.5461 | 0.069* | |
C30 | 0.6873 (4) | 0.6504 (4) | 0.4721 (2) | 0.0465 (9) | |
C31 | 0.5894 (5) | 0.7748 (4) | 0.36256 (19) | 0.0588 (11) | |
H31C | 0.6929 | 0.7869 | 0.3519 | 0.071* | |
H31B | 0.5122 | 0.8589 | 0.3532 | 0.071* | |
H31A | 0.5833 | 0.7186 | 0.3342 | 0.071* | |
C32 | 0.4047 (4) | 0.7221 (3) | 0.47162 (18) | 0.0386 (8) | |
C33 | 0.1436 (4) | 0.8122 (3) | 0.46496 (18) | 0.0411 (8) | |
C34 | 0.0756 (6) | 0.9241 (5) | 0.3460 (2) | 0.0720 (14) | |
H34A | 0.1705 | 0.8604 | 0.3304 | 0.086* | |
H34B | 0.0935 | 1.0094 | 0.3354 | 0.086* | |
H34C | −0.0077 | 0.9279 | 0.3227 | 0.086* | |
C35 | −0.1298 (5) | 0.9211 (4) | 0.4493 (2) | 0.0515 (10) | |
C36 | −0.3408 (5) | 0.9229 (4) | 0.5498 (2) | 0.0649 (12) | |
H36A | −0.3893 | 0.8598 | 0.5456 | 0.078* | |
H36B | −0.3906 | 1.0086 | 0.5246 | 0.078* | |
H36C | −0.3525 | 0.9259 | 0.5981 | 0.078* | |
C37 | −0.0688 (4) | 0.8092 (4) | 0.5684 (2) | 0.0455 (9) | |
C38 | 0.0974 (4) | 0.7670 (3) | 0.53688 (17) | 0.0376 (7) | |
N1 | 0.8576 (4) | 0.1681 (3) | −0.04580 (16) | 0.0519 (8) | |
N2 | 0.8604 (4) | −0.0233 (3) | −0.07896 (16) | 0.0522 (8) | |
N3 | 0.7300 (4) | −0.1727 (3) | −0.00823 (15) | 0.0470 (7) | |
N4 | 0.6006 (4) | −0.3263 (3) | 0.05688 (17) | 0.0545 (8) | |
N5 | 0.4385 (4) | −0.3039 (3) | 0.16596 (16) | 0.0518 (8) | |
N6 | 0.6570 (3) | 0.5847 (3) | 0.54102 (16) | 0.0441 (7) | |
N7 | 0.5578 (4) | 0.7124 (3) | 0.43777 (15) | 0.0451 (7) | |
N8 | 0.2920 (4) | 0.7919 (3) | 0.43248 (15) | 0.0428 (7) | |
N9 | 0.0297 (4) | 0.8846 (3) | 0.42268 (16) | 0.0483 (8) | |
N10 | −0.1716 (3) | 0.8834 (3) | 0.52074 (17) | 0.0471 (7) | |
O1 | 0.7445 (4) | 0.2088 (3) | 0.06135 (16) | 0.0782 (10) | |
O2 | 0.9736 (4) | 0.1306 (3) | −0.15385 (15) | 0.0748 (9) | |
O3 | 0.4617 (5) | −0.4732 (3) | 0.11551 (19) | 0.0890 (11) | |
O4 | 0.4062 (4) | −0.1330 (3) | 0.21484 (15) | 0.0713 (9) | |
O5 | 0.4976 (3) | 0.4989 (3) | 0.63411 (14) | 0.0533 (7) | |
O6 | 0.8207 (3) | 0.6520 (3) | 0.44300 (15) | 0.0611 (8) | |
O7 | −0.2280 (3) | 0.9851 (3) | 0.41175 (16) | 0.0687 (9) | |
O8 | −0.1205 (3) | 0.7855 (3) | 0.63026 (15) | 0.0720 (9) | |
F1 | 0.4364 (3) | 0.2782 (3) | 0.30224 (13) | 0.0746 (8) | |
F2 | 0.1014 (4) | 0.4928 (4) | 0.86628 (13) | 0.1061 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.059 (2) | 0.051 (2) | 0.050 (2) | −0.0282 (19) | 0.0049 (19) | −0.0228 (18) |
C2 | 0.056 (3) | 0.053 (2) | 0.066 (3) | −0.0056 (19) | −0.012 (2) | −0.022 (2) |
C3 | 0.061 (3) | 0.055 (2) | 0.049 (2) | −0.0068 (19) | −0.025 (2) | −0.0112 (18) |
C4 | 0.046 (2) | 0.0394 (18) | 0.0365 (17) | −0.0160 (15) | −0.0070 (15) | −0.0087 (14) |
C5 | 0.048 (2) | 0.0452 (19) | 0.0410 (19) | −0.0128 (16) | −0.0117 (16) | −0.0084 (16) |
C6 | 0.063 (3) | 0.057 (2) | 0.0408 (19) | −0.031 (2) | −0.0129 (18) | −0.0079 (17) |
C7 | 0.044 (2) | 0.047 (2) | 0.0350 (17) | −0.0122 (15) | −0.0124 (15) | −0.0086 (15) |
C8 | 0.043 (2) | 0.048 (2) | 0.0358 (18) | −0.0124 (16) | −0.0086 (15) | −0.0096 (15) |
C9 | 0.052 (2) | 0.053 (2) | 0.044 (2) | −0.0180 (18) | −0.0062 (18) | −0.0072 (18) |
C10 | 0.070 (3) | 0.062 (3) | 0.068 (3) | −0.030 (2) | 0.000 (2) | 0.004 (2) |
C11 | 0.042 (2) | 0.066 (3) | 0.047 (2) | −0.0083 (19) | −0.0033 (18) | −0.006 (2) |
C12 | 0.067 (3) | 0.092 (4) | 0.056 (3) | −0.020 (3) | 0.007 (2) | −0.033 (3) |
C13 | 0.041 (2) | 0.053 (2) | 0.0381 (18) | −0.0092 (16) | −0.0122 (16) | −0.0084 (16) |
C14 | 0.050 (2) | 0.0427 (19) | 0.043 (2) | −0.0110 (16) | −0.0190 (17) | −0.0065 (16) |
C15 | 0.112 (4) | 0.058 (3) | 0.072 (3) | −0.022 (3) | −0.015 (3) | −0.031 (2) |
C16 | 0.082 (3) | 0.048 (2) | 0.059 (3) | −0.023 (2) | −0.025 (2) | −0.005 (2) |
C17 | 0.086 (3) | 0.063 (3) | 0.062 (3) | −0.039 (2) | −0.017 (2) | 0.003 (2) |
C18 | 0.063 (3) | 0.047 (2) | 0.044 (2) | −0.0243 (18) | −0.0137 (18) | −0.0045 (17) |
C19 | 0.050 (2) | 0.0444 (19) | 0.0366 (18) | −0.0132 (16) | −0.0136 (16) | −0.0078 (15) |
C20 | 0.074 (3) | 0.075 (3) | 0.037 (2) | −0.036 (2) | −0.006 (2) | −0.001 (2) |
C21 | 0.076 (3) | 0.069 (3) | 0.056 (2) | −0.045 (2) | −0.005 (2) | 0.000 (2) |
C22 | 0.050 (2) | 0.053 (2) | 0.048 (2) | −0.0232 (17) | −0.0095 (17) | −0.0095 (18) |
C23 | 0.0302 (16) | 0.0394 (17) | 0.0369 (17) | −0.0058 (13) | −0.0087 (14) | −0.0062 (14) |
C24 | 0.050 (2) | 0.049 (2) | 0.048 (2) | −0.0201 (17) | −0.0113 (17) | −0.0097 (17) |
C25 | 0.064 (3) | 0.069 (3) | 0.046 (2) | −0.025 (2) | −0.011 (2) | −0.017 (2) |
C26 | 0.0379 (18) | 0.0311 (16) | 0.0408 (18) | −0.0106 (13) | −0.0107 (15) | −0.0072 (14) |
C27 | 0.0343 (18) | 0.0362 (17) | 0.0389 (17) | −0.0080 (13) | −0.0095 (14) | −0.0070 (14) |
C28 | 0.0352 (18) | 0.0355 (17) | 0.0450 (19) | −0.0046 (14) | −0.0108 (15) | −0.0092 (15) |
C29 | 0.034 (2) | 0.066 (3) | 0.067 (3) | −0.0052 (18) | −0.0152 (19) | −0.011 (2) |
C30 | 0.039 (2) | 0.047 (2) | 0.056 (2) | −0.0112 (16) | −0.0043 (18) | −0.0194 (18) |
C31 | 0.058 (3) | 0.062 (3) | 0.046 (2) | −0.019 (2) | 0.0027 (19) | −0.0015 (19) |
C32 | 0.0396 (19) | 0.0370 (17) | 0.0424 (18) | −0.0098 (14) | −0.0080 (15) | −0.0133 (15) |
C33 | 0.045 (2) | 0.0364 (18) | 0.0447 (19) | −0.0074 (15) | −0.0187 (16) | −0.0076 (15) |
C34 | 0.081 (3) | 0.078 (3) | 0.047 (2) | −0.007 (3) | −0.027 (2) | −0.001 (2) |
C35 | 0.053 (2) | 0.047 (2) | 0.058 (2) | −0.0073 (18) | −0.028 (2) | −0.0092 (18) |
C36 | 0.039 (2) | 0.071 (3) | 0.082 (3) | −0.004 (2) | −0.022 (2) | −0.015 (2) |
C37 | 0.0374 (19) | 0.048 (2) | 0.050 (2) | −0.0067 (16) | −0.0126 (17) | −0.0100 (17) |
C38 | 0.0356 (18) | 0.0374 (17) | 0.0412 (18) | −0.0079 (14) | −0.0131 (15) | −0.0072 (15) |
N1 | 0.0486 (19) | 0.0530 (19) | 0.0480 (18) | −0.0177 (15) | −0.0026 (15) | 0.0000 (15) |
N2 | 0.0476 (19) | 0.064 (2) | 0.0433 (17) | −0.0147 (16) | −0.0018 (15) | −0.0147 (16) |
N3 | 0.0503 (19) | 0.0531 (18) | 0.0411 (16) | −0.0118 (15) | −0.0114 (14) | −0.0155 (14) |
N4 | 0.071 (2) | 0.0483 (18) | 0.0509 (19) | −0.0167 (16) | −0.0167 (17) | −0.0157 (15) |
N5 | 0.065 (2) | 0.0492 (18) | 0.0453 (18) | −0.0252 (16) | −0.0122 (16) | −0.0011 (15) |
N6 | 0.0321 (15) | 0.0491 (17) | 0.0493 (17) | −0.0042 (13) | −0.0113 (13) | −0.0118 (14) |
N7 | 0.0413 (17) | 0.0483 (17) | 0.0429 (16) | −0.0133 (13) | −0.0017 (14) | −0.0078 (14) |
N8 | 0.0450 (18) | 0.0425 (16) | 0.0392 (15) | −0.0093 (13) | −0.0102 (14) | −0.0062 (13) |
N9 | 0.0501 (19) | 0.0480 (18) | 0.0450 (17) | −0.0068 (14) | −0.0207 (14) | −0.0042 (14) |
N10 | 0.0335 (16) | 0.0469 (17) | 0.0596 (19) | −0.0033 (13) | −0.0192 (14) | −0.0088 (15) |
O1 | 0.114 (3) | 0.077 (2) | 0.0609 (19) | −0.061 (2) | 0.0169 (18) | −0.0278 (17) |
O2 | 0.065 (2) | 0.092 (2) | 0.0536 (18) | −0.0229 (17) | 0.0123 (15) | −0.0082 (17) |
O3 | 0.135 (3) | 0.064 (2) | 0.087 (2) | −0.055 (2) | −0.015 (2) | −0.0165 (18) |
O4 | 0.090 (2) | 0.078 (2) | 0.0577 (18) | −0.0478 (18) | 0.0144 (16) | −0.0253 (16) |
O5 | 0.0413 (15) | 0.0524 (15) | 0.0547 (16) | −0.0080 (12) | −0.0133 (12) | 0.0070 (13) |
O6 | 0.0390 (15) | 0.0728 (19) | 0.0664 (18) | −0.0159 (13) | 0.0013 (13) | −0.0137 (15) |
O7 | 0.0583 (18) | 0.0715 (19) | 0.0726 (19) | −0.0025 (15) | −0.0401 (16) | −0.0027 (16) |
O8 | 0.0363 (15) | 0.107 (3) | 0.0541 (18) | −0.0014 (15) | −0.0083 (13) | −0.0079 (17) |
F1 | 0.0872 (19) | 0.0824 (18) | 0.0699 (16) | −0.0328 (15) | 0.0044 (14) | −0.0452 (14) |
F2 | 0.150 (3) | 0.144 (3) | 0.0419 (14) | −0.089 (2) | −0.0125 (16) | 0.0096 (16) |
C1—F1 | 1.360 (4) | C20—C21 | 1.362 (6) |
C1—C2 | 1.361 (5) | C20—C25 | 1.365 (6) |
C1—C6 | 1.366 (6) | C20—F2 | 1.379 (4) |
C2—C3 | 1.377 (5) | C21—C22 | 1.398 (5) |
C2—H2 | 0.93 | C21—H21 | 0.93 |
C3—C4 | 1.379 (5) | C22—C23 | 1.383 (5) |
C3—H3 | 0.93 | C22—H22 | 0.93 |
C4—C5 | 1.382 (4) | C23—C24 | 1.376 (5) |
C4—C7 | 1.493 (5) | C23—C26 | 1.516 (5) |
C5—C6 | 1.378 (5) | C24—C25 | 1.392 (5) |
C5—H5 | 0.93 | C24—H24 | 0.93 |
C6—H6 | 0.93 | C25—H25 | 0.93 |
C7—C19 | 1.408 (5) | C26—C27 | 1.401 (5) |
C7—C8 | 1.419 (5) | C26—C38 | 1.417 (4) |
C8—C13 | 1.403 (5) | C27—C32 | 1.417 (5) |
C8—C9 | 1.474 (5) | C27—C28 | 1.471 (4) |
C9—O1 | 1.205 (4) | C28—O5 | 1.222 (4) |
C9—N1 | 1.409 (5) | C28—N6 | 1.408 (5) |
C10—N1 | 1.473 (5) | C29—N6 | 1.470 (4) |
C10—H10A | 0.96 | C29—H29A | 0.96 |
C10—H10B | 0.96 | C29—H29B | 0.96 |
C10—H10C | 0.96 | C29—H29C | 0.96 |
C11—O2 | 1.221 (5) | C30—O6 | 1.222 (4) |
C11—N1 | 1.382 (5) | C30—N7 | 1.388 (5) |
C11—N2 | 1.384 (5) | C30—N6 | 1.396 (5) |
C12—N2 | 1.469 (5) | C31—N7 | 1.493 (5) |
C12—H12A | 0.96 | C31—H31C | 0.96 |
C12—H12B | 0.96 | C31—H31B | 0.96 |
C12—H12C | 0.96 | C31—H31A | 0.96 |
C13—N3 | 1.334 (5) | C32—N8 | 1.339 (4) |
C13—N2 | 1.394 (5) | C32—N7 | 1.383 (4) |
C14—N3 | 1.344 (5) | C33—N8 | 1.329 (5) |
C14—N4 | 1.379 (5) | C33—N9 | 1.391 (4) |
C14—C19 | 1.401 (5) | C33—C38 | 1.414 (5) |
C15—N4 | 1.472 (5) | C34—N9 | 1.488 (5) |
C15—H15A | 0.96 | C34—H34A | 0.96 |
C15—H15B | 0.96 | C34—H34B | 0.96 |
C15—H15C | 0.96 | C34—H34C | 0.96 |
C16—O3 | 1.213 (5) | C35—O7 | 1.216 (4) |
C16—N5 | 1.375 (5) | C35—N9 | 1.386 (5) |
C16—N4 | 1.403 (6) | C35—N10 | 1.386 (5) |
C17—N5 | 1.487 (5) | C36—N10 | 1.474 (5) |
C17—H17A | 0.96 | C36—H36A | 0.96 |
C17—H17B | 0.96 | C36—H36B | 0.96 |
C17—H17C | 0.96 | C36—H36C | 0.96 |
C18—O4 | 1.208 (4) | C37—O8 | 1.216 (4) |
C18—N5 | 1.395 (5) | C37—N10 | 1.399 (4) |
C18—C19 | 1.481 (5) | C37—C38 | 1.466 (5) |
F1—C1—C2 | 118.6 (4) | C23—C24—H24 | 119.8 |
F1—C1—C6 | 118.4 (4) | C25—C24—H24 | 119.8 |
C2—C1—C6 | 123.0 (3) | C20—C25—C24 | 118.7 (4) |
C1—C2—C3 | 117.9 (4) | C20—C25—H25 | 120.7 |
C1—C2—H2 | 121 | C24—C25—H25 | 120.7 |
C3—C2—H2 | 121 | C27—C26—C38 | 117.9 (3) |
C2—C3—C4 | 120.6 (3) | C27—C26—C23 | 120.8 (3) |
C2—C3—H3 | 119.7 | C38—C26—C23 | 121.3 (3) |
C4—C3—H3 | 119.7 | C26—C27—C32 | 118.5 (3) |
C3—C4—C5 | 120.0 (3) | C26—C27—C28 | 122.7 (3) |
C3—C4—C7 | 119.9 (3) | C32—C27—C28 | 118.7 (3) |
C5—C4—C7 | 120.0 (3) | O5—C28—N6 | 120.3 (3) |
C6—C5—C4 | 119.6 (3) | O5—C28—C27 | 125.3 (3) |
C6—C5—H5 | 120.2 | N6—C28—C27 | 114.4 (3) |
C4—C5—H5 | 120.2 | N6—C29—H29A | 109.5 |
C1—C6—C5 | 118.7 (3) | N6—C29—H29B | 109.5 |
C1—C6—H6 | 120.6 | H29A—C29—H29B | 109.5 |
C5—C6—H6 | 120.6 | N6—C29—H29C | 109.5 |
C19—C7—C8 | 119.1 (3) | H29A—C29—H29C | 109.5 |
C19—C7—C4 | 120.4 (3) | H29B—C29—H29C | 109.5 |
C8—C7—C4 | 120.5 (3) | O6—C30—N7 | 121.5 (4) |
C13—C8—C7 | 117.8 (3) | O6—C30—N6 | 122.1 (3) |
C13—C8—C9 | 118.6 (3) | N7—C30—N6 | 116.4 (3) |
C7—C8—C9 | 123.6 (3) | N7—C31—H31C | 109.5 |
O1—C9—N1 | 118.8 (4) | N7—C31—H31B | 109.5 |
O1—C9—C8 | 125.3 (4) | H31C—C31—H31B | 109.5 |
N1—C9—C8 | 115.9 (3) | N7—C31—H31A | 109.5 |
N1—C10—H10A | 109.5 | H31C—C31—H31A | 109.5 |
N1—C10—H10B | 109.5 | H31B—C31—H31A | 109.5 |
H10A—C10—H10B | 109.5 | N8—C32—N7 | 115.2 (3) |
N1—C10—H10C | 109.5 | N8—C32—C27 | 124.0 (3) |
H10A—C10—H10C | 109.5 | N7—C32—C27 | 120.8 (3) |
H10B—C10—H10C | 109.5 | N8—C33—N9 | 115.0 (3) |
O2—C11—N1 | 120.6 (4) | N8—C33—C38 | 125.1 (3) |
O2—C11—N2 | 123.4 (4) | N9—C33—C38 | 119.9 (3) |
N1—C11—N2 | 115.9 (4) | N9—C34—H34A | 109.5 |
N2—C12—H12A | 109.5 | N9—C34—H34B | 109.5 |
N2—C12—H12B | 109.5 | H34A—C34—H34B | 109.5 |
H12A—C12—H12B | 109.5 | N9—C34—H34C | 109.5 |
N2—C12—H12C | 109.5 | H34A—C34—H34C | 109.5 |
H12A—C12—H12C | 109.5 | H34B—C34—H34C | 109.5 |
H12B—C12—H12C | 109.5 | O7—C35—N9 | 121.3 (4) |
N3—C13—N2 | 116.5 (3) | O7—C35—N10 | 121.8 (4) |
N3—C13—C8 | 123.4 (3) | N9—C35—N10 | 116.9 (3) |
N2—C13—C8 | 120.1 (4) | N10—C36—H36A | 109.5 |
N3—C14—N4 | 116.5 (3) | N10—C36—H36B | 109.5 |
N3—C14—C19 | 124.0 (3) | H36A—C36—H36B | 109.5 |
N4—C14—C19 | 119.6 (4) | N10—C36—H36C | 109.5 |
N4—C15—H15A | 109.5 | H36A—C36—H36C | 109.5 |
N4—C15—H15B | 109.5 | H36B—C36—H36C | 109.5 |
H15A—C15—H15B | 109.5 | O8—C37—N10 | 119.8 (3) |
N4—C15—H15C | 109.5 | O8—C37—C38 | 125.8 (3) |
H15A—C15—H15C | 109.5 | N10—C37—C38 | 114.4 (3) |
H15B—C15—H15C | 109.5 | C33—C38—C26 | 117.6 (3) |
O3—C16—N5 | 121.6 (5) | C33—C38—C37 | 120.0 (3) |
O3—C16—N4 | 121.6 (4) | C26—C38—C37 | 122.3 (3) |
N5—C16—N4 | 116.8 (4) | C11—N1—C9 | 125.6 (4) |
N5—C17—H17A | 109.5 | C11—N1—C10 | 116.2 (4) |
N5—C17—H17B | 109.5 | C9—N1—C10 | 118.2 (3) |
H17A—C17—H17B | 109.5 | C11—N2—C13 | 123.5 (3) |
N5—C17—H17C | 109.5 | C11—N2—C12 | 114.9 (4) |
H17A—C17—H17C | 109.5 | C13—N2—C12 | 121.5 (4) |
H17B—C17—H17C | 109.5 | C13—N3—C14 | 118.3 (3) |
O4—C18—N5 | 118.2 (4) | C14—N4—C16 | 123.2 (3) |
O4—C18—C19 | 125.8 (4) | C14—N4—C15 | 121.2 (4) |
N5—C18—C19 | 116.0 (3) | C16—N4—C15 | 115.5 (4) |
C14—C19—C7 | 117.4 (3) | C16—N5—C18 | 125.0 (4) |
C14—C19—C18 | 119.4 (3) | C16—N5—C17 | 116.7 (4) |
C7—C19—C18 | 123.2 (3) | C18—N5—C17 | 118.3 (3) |
C21—C20—C25 | 122.9 (4) | C30—N6—C28 | 125.8 (3) |
C21—C20—F2 | 117.9 (4) | C30—N6—C29 | 117.7 (3) |
C25—C20—F2 | 119.2 (4) | C28—N6—C29 | 116.4 (3) |
C20—C21—C22 | 117.9 (4) | C32—N7—C30 | 122.2 (3) |
C20—C21—H21 | 121 | C32—N7—C31 | 120.6 (3) |
C22—C21—H21 | 121 | C30—N7—C31 | 117.1 (3) |
C23—C22—C21 | 120.7 (3) | C33—N8—C32 | 116.6 (3) |
C23—C22—H22 | 119.7 | C35—N9—C33 | 122.1 (3) |
C21—C22—H22 | 119.7 | C35—N9—C34 | 117.3 (3) |
C24—C23—C22 | 119.5 (3) | C33—N9—C34 | 120.6 (3) |
C24—C23—C26 | 117.7 (3) | C35—N10—C37 | 126.4 (3) |
C22—C23—C26 | 122.7 (3) | C35—N10—C36 | 117.4 (3) |
C23—C24—C25 | 120.3 (4) | C37—N10—C36 | 116.2 (3) |
F1—C1—C2—C3 | 177.2 (4) | O8—C37—C38—C26 | 2.9 (6) |
C6—C1—C2—C3 | −2.3 (7) | N10—C37—C38—C26 | −177.3 (3) |
C1—C2—C3—C4 | 1.1 (7) | O2—C11—N1—C9 | 177.7 (4) |
C2—C3—C4—C5 | 0.2 (6) | N2—C11—N1—C9 | −2.7 (5) |
C2—C3—C4—C7 | −177.6 (4) | O2—C11—N1—C10 | −2.8 (6) |
C3—C4—C5—C6 | −0.5 (6) | N2—C11—N1—C10 | 176.9 (3) |
C7—C4—C5—C6 | 177.3 (3) | O1—C9—N1—C11 | 177.3 (4) |
F1—C1—C6—C5 | −177.5 (3) | C8—C9—N1—C11 | −2.2 (5) |
C2—C1—C6—C5 | 2.0 (6) | O1—C9—N1—C10 | −2.3 (6) |
C4—C5—C6—C1 | −0.6 (6) | C8—C9—N1—C10 | 178.2 (3) |
C3—C4—C7—C19 | −97.7 (4) | O2—C11—N2—C13 | −174.3 (4) |
C5—C4—C7—C19 | 84.5 (4) | N1—C11—N2—C13 | 6.1 (5) |
C3—C4—C7—C8 | 82.6 (5) | O2—C11—N2—C12 | 4.2 (6) |
C5—C4—C7—C8 | −95.3 (4) | N1—C11—N2—C12 | −175.5 (3) |
C19—C7—C8—C13 | −0.9 (5) | N3—C13—N2—C11 | 176.5 (3) |
C4—C7—C8—C13 | 178.8 (3) | C8—C13—N2—C11 | −4.4 (5) |
C19—C7—C8—C9 | 179.4 (3) | N3—C13—N2—C12 | −1.9 (5) |
C4—C7—C8—C9 | −0.8 (5) | C8—C13—N2—C12 | 177.3 (3) |
C13—C8—C9—O1 | −175.5 (4) | N2—C13—N3—C14 | −178.6 (3) |
C7—C8—C9—O1 | 4.2 (6) | C8—C13—N3—C14 | 2.2 (5) |
C13—C8—C9—N1 | 4.0 (5) | N4—C14—N3—C13 | 179.4 (3) |
C7—C8—C9—N1 | −176.4 (3) | C19—C14—N3—C13 | −0.5 (5) |
C7—C8—C13—N3 | −1.5 (5) | N3—C14—N4—C16 | −176.3 (3) |
C9—C8—C13—N3 | 178.1 (3) | C19—C14—N4—C16 | 3.6 (5) |
C7—C8—C13—N2 | 179.4 (3) | N3—C14—N4—C15 | 7.6 (5) |
C9—C8—C13—N2 | −1.0 (5) | C19—C14—N4—C15 | −172.6 (4) |
N3—C14—C19—C7 | −1.8 (5) | O3—C16—N4—C14 | 176.1 (4) |
N4—C14—C19—C7 | 178.3 (3) | N5—C16—N4—C14 | −2.9 (6) |
N3—C14—C19—C18 | 177.0 (3) | O3—C16—N4—C15 | −7.5 (6) |
N4—C14—C19—C18 | −2.8 (5) | N5—C16—N4—C15 | 173.5 (4) |
C8—C7—C19—C14 | 2.5 (5) | O3—C16—N5—C18 | −177.4 (4) |
C4—C7—C19—C14 | −177.3 (3) | N4—C16—N5—C18 | 1.6 (6) |
C8—C7—C19—C18 | −176.4 (3) | O3—C16—N5—C17 | 3.2 (6) |
C4—C7—C19—C18 | 3.9 (5) | N4—C16—N5—C17 | −177.8 (3) |
O4—C18—C19—C14 | −177.4 (4) | O4—C18—N5—C16 | 178.0 (4) |
N5—C18—C19—C14 | 1.5 (5) | C19—C18—N5—C16 | −0.9 (5) |
O4—C18—C19—C7 | 1.5 (6) | O4—C18—N5—C17 | −2.7 (5) |
N5—C18—C19—C7 | −179.7 (3) | C19—C18—N5—C17 | 178.4 (3) |
C25—C20—C21—C22 | 0.6 (7) | O6—C30—N6—C28 | −178.1 (3) |
F2—C20—C21—C22 | −179.7 (4) | N7—C30—N6—C28 | 0.9 (5) |
C20—C21—C22—C23 | −0.2 (6) | O6—C30—N6—C29 | −1.7 (5) |
C21—C22—C23—C24 | −0.2 (6) | N7—C30—N6—C29 | 177.3 (3) |
C21—C22—C23—C26 | 177.1 (4) | O5—C28—N6—C30 | 169.1 (3) |
C22—C23—C24—C25 | 0.2 (5) | C27—C28—N6—C30 | −11.1 (5) |
C26—C23—C24—C25 | −177.2 (3) | O5—C28—N6—C29 | −7.4 (5) |
C21—C20—C25—C24 | −0.6 (7) | C27—C28—N6—C29 | 172.4 (3) |
F2—C20—C25—C24 | 179.7 (4) | N8—C32—N7—C30 | 176.0 (3) |
C23—C24—C25—C20 | 0.2 (6) | C27—C32—N7—C30 | −3.8 (5) |
C24—C23—C26—C27 | 71.1 (4) | N8—C32—N7—C31 | −1.1 (5) |
C22—C23—C26—C27 | −106.2 (4) | C27—C32—N7—C31 | 179.1 (3) |
C24—C23—C26—C38 | −105.6 (4) | O6—C30—N7—C32 | −173.9 (3) |
C22—C23—C26—C38 | 77.1 (4) | N6—C30—N7—C32 | 7.1 (5) |
C38—C26—C27—C32 | 2.5 (4) | O6—C30—N7—C31 | 3.4 (5) |
C23—C26—C27—C32 | −174.3 (3) | N6—C30—N7—C31 | −175.7 (3) |
C38—C26—C27—C28 | −177.3 (3) | N9—C33—N8—C32 | −179.8 (3) |
C23—C26—C27—C28 | 5.9 (5) | C38—C33—N8—C32 | 0.6 (5) |
C26—C27—C28—O5 | 13.4 (5) | N7—C32—N8—C33 | −174.7 (3) |
C32—C27—C28—O5 | −166.4 (3) | C27—C32—N8—C33 | 5.1 (5) |
C26—C27—C28—N6 | −166.4 (3) | O7—C35—N9—C33 | 179.6 (4) |
C32—C27—C28—N6 | 13.8 (4) | N10—C35—N9—C33 | 0.8 (5) |
C26—C27—C32—N8 | −6.8 (5) | O7—C35—N9—C34 | −1.5 (6) |
C28—C27—C32—N8 | 173.0 (3) | N10—C35—N9—C34 | 179.7 (3) |
C26—C27—C32—N7 | 173.0 (3) | N8—C33—N9—C35 | −176.0 (3) |
C28—C27—C32—N7 | −7.2 (5) | C38—C33—N9—C35 | 3.6 (5) |
N8—C33—C38—C26 | −4.5 (5) | N8—C33—N9—C34 | 5.1 (5) |
N9—C33—C38—C26 | 176.0 (3) | C38—C33—N9—C34 | −175.3 (4) |
N8—C33—C38—C37 | 172.5 (3) | O7—C35—N10—C37 | 179.5 (4) |
N9—C33—C38—C37 | −7.1 (5) | N9—C35—N10—C37 | −1.7 (6) |
C27—C26—C38—C33 | 2.6 (4) | O7—C35—N10—C36 | 0.6 (6) |
C23—C26—C38—C33 | 179.4 (3) | N9—C35—N10—C36 | 179.4 (3) |
C27—C26—C38—C37 | −174.3 (3) | O8—C37—N10—C35 | 178.2 (4) |
C23—C26—C38—C37 | 2.5 (5) | C38—C37—N10—C35 | −1.6 (5) |
O8—C37—C38—C33 | −173.9 (4) | O8—C37—N10—C36 | −2.9 (5) |
N10—C37—C38—C33 | 5.9 (5) | C38—C37—N10—C36 | 177.3 (3) |
Experimental details
Crystal data | |
Chemical formula | C19H16FN5O4 |
Mr | 397.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 9.074 (2), 10.930 (3), 20.091 (5) |
α, β, γ (°) | 75.04 (2), 76.82 (2), 70.93 (2) |
V (Å3) | 1796.8 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.25 × 0.25 × 0.04 |
Data collection | |
Diffractometer | Stoe IPDSII |
Absorption correction | Numerical shape of crystal determined optically (X-RED32 and X-SHAPE; Stoe & Cie, 2005) |
Tmin, Tmax | 0.950, 0.995 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15435, 8540, 5359 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.098, 0.184, 1.23 |
No. of reflections | 8540 |
No. of parameters | 531 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.24 |
Computer programs: X-AREA (Stoe & Cie, 2005), X-AREA, X-RED32 (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
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Pyridopyrimidines are annelated uracils that have attracted considerable interest in recent years. Their derivatives have been known to display a wide range of pharmacological activities, such as antitumor (Sanghhvi et al., 1989), antiviral (Tenser et al., 2001) and antifungal (Nizamuddin-Mishra et al., 2001). Therefore, for the preparation of these complex molecules large efforts have been directed towards the synthetic manipulation of uracils. As a result, a number of reports have appeared in the literature that usually describe forcing conditions, long reaction times and complex synthetic pathways. Thus, new routes for the synthesis of these molecules have attracted considerable attention allowing for a rapid entry to these heterocycles. Microwave-assisted organic synthesis is an increasingly popular field as indicated by numerous publications in the past few years owing to several advantages, such as enhanced reaction rates and increase in yields under milder conditions (Perreux & Loupy, 2001). In light of the above, we have synthesized the title compound, (I), under microwave-assisted conditions and characterized its structure.
In the molecule of (I), (Fig. 1), the bond lengths and angles are generally within normal ranges (Allen et al., 1987) and may be compared with the corresponding ones in similar structures (Bazgir et al., 2006a,b). The asymmetric unit contains two independent molecules.
Rings A (N1/N2/C87C9/C11), B (N3/C7/C8/C13/C14/C19), C (N4/N5/C14/C16/C187C19) D (C1—C6) and A' (N6/N7/C27/C28/C30/C32), B' (N8/C26/C27/C32/C33/C38), C' (N9/N10/C33/C35/C37/C38), D' (C20—C25) are, of course, planar and the dihedral angles between them are A/B = 2.62 (2), A/C = 5.08 (3), B/C = 2.48 (2) and A'/B' = 7.58 (2), A'/C' = 12.28 (3), B'/C' = 4.92 (3)°.
The weak π-π stacking interactions, involving the adjacent rings with centroid-centroid distance of 3.507 (4) %A [symmetry code: x, y + 1/2, z] may be effective in the stabilization of the crystal structure.