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Acta Cryst. (2007). E63, o2790    [ doi:10.1107/S1600536807020454 ]

5-(4-Fluorophenyl)-1,3,7,9-tetramethylpyrido[2,3-d:6,5-d]dipyrimidine-2,4,6,8(1H,3H,7H,9H)-tetrone

H. Ghorbani and A. Bazgir

Abstract top

The asymmetric unit of the title compound, C19H16FN5O4, contains two independent molecules. The dihedral angles between the main planes and the fluorophenyl rings in the two molecules are 83.24 (5) and 71.76 (4)°. Weak [pi]-[pi] stacking interactions may be effective in the stabilization of the crystal structure.

Comment top

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.

Related literature top

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).

Experimental top

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).

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
5-Fluorophenyl-1,3,7,9-tetramethylpyrido[2,3 - d:6,5 - d]dipyrimidine- 2,4,6,8(1H,3H,7H,9H)-tetrone top
Crystal data top
C19H16FN5O4Z = 4
Mr = 397.37F(000) = 824
Triclinic, P1Dx = 1.469 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.074 (2) ÅCell parameters from 2000 reflections
b = 10.930 (3) Åθ = 2.0–28.0°
c = 20.091 (5) ŵ = 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
Data collection top
Stoe IPDSII
diffractometer		5359 reflections with I > 2σ(I)
rotation method scansRint = 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 = 0.995h = −11→11
15435 measured reflectionsk = −12→14
8540 independent reflectionsl = −26→26
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-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 = 1.23Δρmax = 0.19 e Å−3
8540 reflectionsΔρmin = −0.23 e Å−3
531 parameters
Crystal data top
C19H16FN5O4γ = 70.93 (2)°
Mr = 397.37V = 1796.8 (8) Å3
Triclinic, P1Z = 4
a = 9.074 (2) ÅMo Kα radiation
b = 10.930 (3) ŵ = 0.11 mm−1
c = 20.091 (5) ÅT = 294 K
α = 75.04 (2)°0.25 × 0.25 × 0.04 mm
β = 76.82 (2)°
Data collection top
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 = 0.995Rint = 0.050
15435 measured reflectionsθmax = 28.0°
Refinement top
R[F2 > 2σ(F2)] = 0.098H-atom parameters constrained
wR(F2) = 0.184Δρmax = 0.19 e Å−3
S = 1.23Δρmin = −0.23 e Å−3
8540 reflectionsAbsolute structure: ?
531 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4778 (5)0.2016 (4)0.2535 (2)0.0503 (9)
C20.3908 (5)0.2376 (4)0.2011 (2)0.0587 (11)
H20.30210.31070.19950.07*
C30.4381 (5)0.1625 (4)0.1504 (2)0.0546 (10)
H30.38180.18580.11350.066*
C40.5682 (4)0.0530 (3)0.15386 (17)0.0393 (8)
C50.6521 (4)0.0174 (4)0.20864 (18)0.0442 (8)
H50.7394−0.05680.21130.053*
C60.6056 (5)0.0925 (4)0.25931 (19)0.0499 (9)
H60.66030.06950.29670.06*
C70.6216 (4)−0.0241 (3)0.09701 (17)0.0410 (8)
C80.7181 (4)0.0176 (3)0.03454 (17)0.0417 (8)
C90.7701 (5)0.1376 (4)0.0207 (2)0.0496 (9)
C100.9087 (6)0.2890 (4)−0.0633 (2)0.0691 (12)
H10A0.91990.3093−0.02130.083*
H10B0.83120.361−0.0860.083*
H10C1.00810.2754−0.09390.083*
C110.9018 (5)0.0935 (4)−0.0969 (2)0.0552 (10)
C120.9192 (6)−0.1058 (5)−0.1321 (2)0.0713 (13)
H12A0.8463−0.0781−0.16460.086*
H12B0.9293−0.1965−0.10990.086*
H12C1.0204−0.0966−0.15630.086*
C130.7668 (4)−0.0605 (4)−0.01636 (18)0.0441 (8)
C140.6372 (4)−0.2105 (4)0.05081 (19)0.0443 (8)
C150.6760 (7)−0.4117 (4)0.0055 (2)0.0777 (15)
H15A0.7724−0.3925−0.01910.093*
H15B0.606−0.3957−0.02720.093*
H15C0.6988−0.50260.0290.093*
C160.4980 (6)−0.3747 (4)0.1134 (2)0.0607 (11)
C170.3346 (6)−0.3582 (5)0.2271 (2)0.0679 (12)
H17A0.2261−0.31530.22170.081*
H17B0.3538−0.34290.26890.081*
H17C0.3568−0.45140.23020.081*
C180.4697 (5)−0.1872 (4)0.1662 (2)0.0490 (9)
C190.5773 (4)−0.1397 (3)0.10484 (18)0.0428 (8)
C200.1273 (5)0.5408 (5)0.7954 (2)0.0605 (11)
C210.0886 (6)0.4813 (5)0.7527 (2)0.0639 (11)
H210.04560.41080.77090.077*
C220.1154 (4)0.5295 (4)0.6808 (2)0.0479 (9)
H220.09030.49040.65050.057*
C230.1790 (4)0.6346 (3)0.65424 (17)0.0362 (7)
C240.2156 (4)0.6923 (4)0.69921 (19)0.0467 (9)
H240.25810.76320.68160.056*
C250.1894 (5)0.6452 (4)0.7709 (2)0.0572 (10)
H250.21360.6840.80150.069*
C260.2175 (4)0.6864 (3)0.57664 (17)0.0356 (7)
C270.3742 (4)0.6615 (3)0.54272 (17)0.0364 (7)
C280.5081 (4)0.5747 (3)0.57779 (18)0.0389 (8)
C290.7927 (4)0.5130 (4)0.5778 (2)0.0572 (10)
H29A0.79220.42260.59520.069*
H29B0.78570.55330.6160.069*
H29C0.88880.51620.54610.069*
C300.6873 (4)0.6504 (4)0.4721 (2)0.0465 (9)
C310.5894 (5)0.7748 (4)0.36256 (19)0.0588 (11)
H31C0.69290.78690.35190.071*
H31B0.51220.85890.35320.071*
H31A0.58330.71860.33420.071*
C320.4047 (4)0.7221 (3)0.47162 (18)0.0386 (8)
C330.1436 (4)0.8122 (3)0.46496 (18)0.0411 (8)
C340.0756 (6)0.9241 (5)0.3460 (2)0.0720 (14)
H34A0.17050.86040.33040.086*
H34B0.09351.00940.33540.086*
H34C−0.00770.92790.32270.086*
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−0.38930.85980.54560.078*
H36B−0.39061.00860.52460.078*
H36C−0.35250.92590.59810.078*
C37−0.0688 (4)0.8092 (4)0.5684 (2)0.0455 (9)
C380.0974 (4)0.7670 (3)0.53688 (17)0.0376 (7)
N10.8576 (4)0.1681 (3)−0.04580 (16)0.0519 (8)
N20.8604 (4)−0.0233 (3)−0.07896 (16)0.0522 (8)
N30.7300 (4)−0.1727 (3)−0.00823 (15)0.0470 (7)
N40.6006 (4)−0.3263 (3)0.05688 (17)0.0545 (8)
N50.4385 (4)−0.3039 (3)0.16596 (16)0.0518 (8)
N60.6570 (3)0.5847 (3)0.54102 (16)0.0441 (7)
N70.5578 (4)0.7124 (3)0.43777 (15)0.0451 (7)
N80.2920 (4)0.7919 (3)0.43248 (15)0.0428 (7)
N90.0297 (4)0.8846 (3)0.42268 (16)0.0483 (8)
N10−0.1716 (3)0.8834 (3)0.52074 (17)0.0471 (7)
O10.7445 (4)0.2088 (3)0.06135 (16)0.0782 (10)
O20.9736 (4)0.1306 (3)−0.15385 (15)0.0748 (9)
O30.4617 (5)−0.4732 (3)0.11551 (19)0.0890 (11)
O40.4062 (4)−0.1330 (3)0.21484 (15)0.0713 (9)
O50.4976 (3)0.4989 (3)0.63411 (14)0.0533 (7)
O60.8207 (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)
F10.4364 (3)0.2782 (3)0.30224 (13)0.0746 (8)
F20.1014 (4)0.4928 (4)0.86628 (13)0.1061 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.059 (2)0.051 (2)0.050 (2)−0.0282 (19)0.0049 (19)−0.0228 (18)
C20.056 (3)0.053 (2)0.066 (3)−0.0056 (19)−0.012 (2)−0.022 (2)
C30.061 (3)0.055 (2)0.049 (2)−0.0068 (19)−0.025 (2)−0.0112 (18)
C40.046 (2)0.0394 (18)0.0365 (17)−0.0160 (15)−0.0070 (15)−0.0087 (14)
C50.048 (2)0.0452 (19)0.0410 (19)−0.0128 (16)−0.0117 (16)−0.0084 (16)
C60.063 (3)0.057 (2)0.0408 (19)−0.031 (2)−0.0129 (18)−0.0079 (17)
C70.044 (2)0.047 (2)0.0350 (17)−0.0122 (15)−0.0124 (15)−0.0086 (15)
C80.043 (2)0.048 (2)0.0358 (18)−0.0124 (16)−0.0086 (15)−0.0096 (15)
C90.052 (2)0.053 (2)0.044 (2)−0.0180 (18)−0.0062 (18)−0.0072 (18)
C100.070 (3)0.062 (3)0.068 (3)−0.030 (2)0.000 (2)0.004 (2)
C110.042 (2)0.066 (3)0.047 (2)−0.0083 (19)−0.0033 (18)−0.006 (2)
C120.067 (3)0.092 (4)0.056 (3)−0.020 (3)0.007 (2)−0.033 (3)
C130.041 (2)0.053 (2)0.0381 (18)−0.0092 (16)−0.0122 (16)−0.0084 (16)
C140.050 (2)0.0427 (19)0.043 (2)−0.0110 (16)−0.0190 (17)−0.0065 (16)
C150.112 (4)0.058 (3)0.072 (3)−0.022 (3)−0.015 (3)−0.031 (2)
C160.082 (3)0.048 (2)0.059 (3)−0.023 (2)−0.025 (2)−0.005 (2)
C170.086 (3)0.063 (3)0.062 (3)−0.039 (2)−0.017 (2)0.003 (2)
C180.063 (3)0.047 (2)0.044 (2)−0.0243 (18)−0.0137 (18)−0.0045 (17)
C190.050 (2)0.0444 (19)0.0366 (18)−0.0132 (16)−0.0136 (16)−0.0078 (15)
C200.074 (3)0.075 (3)0.037 (2)−0.036 (2)−0.006 (2)−0.001 (2)
C210.076 (3)0.069 (3)0.056 (2)−0.045 (2)−0.005 (2)0.000 (2)
C220.050 (2)0.053 (2)0.048 (2)−0.0232 (17)−0.0095 (17)−0.0095 (18)
C230.0302 (16)0.0394 (17)0.0369 (17)−0.0058 (13)−0.0087 (14)−0.0062 (14)
C240.050 (2)0.049 (2)0.048 (2)−0.0201 (17)−0.0113 (17)−0.0097 (17)
C250.064 (3)0.069 (3)0.046 (2)−0.025 (2)−0.011 (2)−0.017 (2)
C260.0379 (18)0.0311 (16)0.0408 (18)−0.0106 (13)−0.0107 (15)−0.0072 (14)
C270.0343 (18)0.0362 (17)0.0389 (17)−0.0080 (13)−0.0095 (14)−0.0070 (14)
C280.0352 (18)0.0355 (17)0.0450 (19)−0.0046 (14)−0.0108 (15)−0.0092 (15)
C290.034 (2)0.066 (3)0.067 (3)−0.0052 (18)−0.0152 (19)−0.011 (2)
C300.039 (2)0.047 (2)0.056 (2)−0.0112 (16)−0.0043 (18)−0.0194 (18)
C310.058 (3)0.062 (3)0.046 (2)−0.019 (2)0.0027 (19)−0.0015 (19)
C320.0396 (19)0.0370 (17)0.0424 (18)−0.0098 (14)−0.0080 (15)−0.0133 (15)
C330.045 (2)0.0364 (18)0.0447 (19)−0.0074 (15)−0.0187 (16)−0.0076 (15)
C340.081 (3)0.078 (3)0.047 (2)−0.007 (3)−0.027 (2)−0.001 (2)
C350.053 (2)0.047 (2)0.058 (2)−0.0073 (18)−0.028 (2)−0.0092 (18)
C360.039 (2)0.071 (3)0.082 (3)−0.004 (2)−0.022 (2)−0.015 (2)
C370.0374 (19)0.048 (2)0.050 (2)−0.0067 (16)−0.0126 (17)−0.0100 (17)
C380.0356 (18)0.0374 (17)0.0412 (18)−0.0079 (14)−0.0131 (15)−0.0072 (15)
N10.0486 (19)0.0530 (19)0.0480 (18)−0.0177 (15)−0.0026 (15)0.0000 (15)
N20.0476 (19)0.064 (2)0.0433 (17)−0.0147 (16)−0.0018 (15)−0.0147 (16)
N30.0503 (19)0.0531 (18)0.0411 (16)−0.0118 (15)−0.0114 (14)−0.0155 (14)
N40.071 (2)0.0483 (18)0.0509 (19)−0.0167 (16)−0.0167 (17)−0.0157 (15)
N50.065 (2)0.0492 (18)0.0453 (18)−0.0252 (16)−0.0122 (16)−0.0011 (15)
N60.0321 (15)0.0491 (17)0.0493 (17)−0.0042 (13)−0.0113 (13)−0.0118 (14)
N70.0413 (17)0.0483 (17)0.0429 (16)−0.0133 (13)−0.0017 (14)−0.0078 (14)
N80.0450 (18)0.0425 (16)0.0392 (15)−0.0093 (13)−0.0102 (14)−0.0062 (13)
N90.0501 (19)0.0480 (18)0.0450 (17)−0.0068 (14)−0.0207 (14)−0.0042 (14)
N100.0335 (16)0.0469 (17)0.0596 (19)−0.0033 (13)−0.0192 (14)−0.0088 (15)
O10.114 (3)0.077 (2)0.0609 (19)−0.061 (2)0.0169 (18)−0.0278 (17)
O20.065 (2)0.092 (2)0.0536 (18)−0.0229 (17)0.0123 (15)−0.0082 (17)
O30.135 (3)0.064 (2)0.087 (2)−0.055 (2)−0.015 (2)−0.0165 (18)
O40.090 (2)0.078 (2)0.0577 (18)−0.0478 (18)0.0144 (16)−0.0253 (16)
O50.0413 (15)0.0524 (15)0.0547 (16)−0.0080 (12)−0.0133 (12)0.0070 (13)
O60.0390 (15)0.0728 (19)0.0664 (18)−0.0159 (13)0.0013 (13)−0.0137 (15)
O70.0583 (18)0.0715 (19)0.0726 (19)−0.0025 (15)−0.0401 (16)−0.0027 (16)
O80.0363 (15)0.107 (3)0.0541 (18)−0.0014 (15)−0.0083 (13)−0.0079 (17)
F10.0872 (19)0.0824 (18)0.0699 (16)−0.0328 (15)0.0044 (14)−0.0452 (14)
F20.150 (3)0.144 (3)0.0419 (14)−0.089 (2)−0.0125 (16)0.0096 (16)
Geometric parameters (Å, °) top
C1—F11.360 (4)C20—C211.362 (6)
C1—C21.361 (5)C20—C251.365 (6)
C1—C61.366 (6)C20—F21.379 (4)
C2—C31.377 (5)C21—C221.398 (5)
C2—H20.93C21—H210.93
C3—C41.379 (5)C22—C231.383 (5)
C3—H30.93C22—H220.93
C4—C51.382 (4)C23—C241.376 (5)
C4—C71.493 (5)C23—C261.516 (5)
C5—C61.378 (5)C24—C251.392 (5)
C5—H50.93C24—H240.93
C6—H60.93C25—H250.93
C7—C191.408 (5)C26—C271.401 (5)
C7—C81.419 (5)C26—C381.417 (4)
C8—C131.403 (5)C27—C321.417 (5)
C8—C91.474 (5)C27—C281.471 (4)
C9—O11.205 (4)C28—O51.222 (4)
C9—N11.409 (5)C28—N61.408 (5)
C10—N11.473 (5)C29—N61.470 (4)
C10—H10A0.96C29—H29A0.96
C10—H10B0.96C29—H29B0.96
C10—H10C0.96C29—H29C0.96
C11—O21.221 (5)C30—O61.222 (4)
C11—N11.382 (5)C30—N71.388 (5)
C11—N21.384 (5)C30—N61.396 (5)
C12—N21.469 (5)C31—N71.493 (5)
C12—H12A0.96C31—H31C0.96
C12—H12B0.96C31—H31B0.96
C12—H12C0.96C31—H31A0.96
C13—N31.334 (5)C32—N81.339 (4)
C13—N21.394 (5)C32—N71.383 (4)
C14—N31.344 (5)C33—N81.329 (5)
C14—N41.379 (5)C33—N91.391 (4)
C14—C191.401 (5)C33—C381.414 (5)
C15—N41.472 (5)C34—N91.488 (5)
C15—H15A0.96C34—H34A0.96
C15—H15B0.96C34—H34B0.96
C15—H15C0.96C34—H34C0.96
C16—O31.213 (5)C35—O71.216 (4)
C16—N51.375 (5)C35—N91.386 (5)
C16—N41.403 (6)C35—N101.386 (5)
C17—N51.487 (5)C36—N101.474 (5)
C17—H17A0.96C36—H36A0.96
C17—H17B0.96C36—H36B0.96
C17—H17C0.96C36—H36C0.96
C18—O41.208 (4)C37—O81.216 (4)
C18—N51.395 (5)C37—N101.399 (4)
C18—C191.481 (5)C37—C381.466 (5)
F1—C1—C2118.6 (4)C23—C24—H24119.8
F1—C1—C6118.4 (4)C25—C24—H24119.8
C2—C1—C6123.0 (3)C20—C25—C24118.7 (4)
C1—C2—C3117.9 (4)C20—C25—H25120.7
C1—C2—H2121C24—C25—H25120.7
C3—C2—H2121C27—C26—C38117.9 (3)
C2—C3—C4120.6 (3)C27—C26—C23120.8 (3)
C2—C3—H3119.7C38—C26—C23121.3 (3)
C4—C3—H3119.7C26—C27—C32118.5 (3)
C3—C4—C5120.0 (3)C26—C27—C28122.7 (3)
C3—C4—C7119.9 (3)C32—C27—C28118.7 (3)
C5—C4—C7120.0 (3)O5—C28—N6120.3 (3)
C6—C5—C4119.6 (3)O5—C28—C27125.3 (3)
C6—C5—H5120.2N6—C28—C27114.4 (3)
C4—C5—H5120.2N6—C29—H29A109.5
C1—C6—C5118.7 (3)N6—C29—H29B109.5
C1—C6—H6120.6H29A—C29—H29B109.5
C5—C6—H6120.6N6—C29—H29C109.5
C19—C7—C8119.1 (3)H29A—C29—H29C109.5
C19—C7—C4120.4 (3)H29B—C29—H29C109.5
C8—C7—C4120.5 (3)O6—C30—N7121.5 (4)
C13—C8—C7117.8 (3)O6—C30—N6122.1 (3)
C13—C8—C9118.6 (3)N7—C30—N6116.4 (3)
C7—C8—C9123.6 (3)N7—C31—H31C109.5
O1—C9—N1118.8 (4)N7—C31—H31B109.5
O1—C9—C8125.3 (4)H31C—C31—H31B109.5
N1—C9—C8115.9 (3)N7—C31—H31A109.5
N1—C10—H10A109.5H31C—C31—H31A109.5
N1—C10—H10B109.5H31B—C31—H31A109.5
H10A—C10—H10B109.5N8—C32—N7115.2 (3)
N1—C10—H10C109.5N8—C32—C27124.0 (3)
H10A—C10—H10C109.5N7—C32—C27120.8 (3)
H10B—C10—H10C109.5N8—C33—N9115.0 (3)
O2—C11—N1120.6 (4)N8—C33—C38125.1 (3)
O2—C11—N2123.4 (4)N9—C33—C38119.9 (3)
N1—C11—N2115.9 (4)N9—C34—H34A109.5
N2—C12—H12A109.5N9—C34—H34B109.5
N2—C12—H12B109.5H34A—C34—H34B109.5
H12A—C12—H12B109.5N9—C34—H34C109.5
N2—C12—H12C109.5H34A—C34—H34C109.5
H12A—C12—H12C109.5H34B—C34—H34C109.5
H12B—C12—H12C109.5O7—C35—N9121.3 (4)
N3—C13—N2116.5 (3)O7—C35—N10121.8 (4)
N3—C13—C8123.4 (3)N9—C35—N10116.9 (3)
N2—C13—C8120.1 (4)N10—C36—H36A109.5
N3—C14—N4116.5 (3)N10—C36—H36B109.5
N3—C14—C19124.0 (3)H36A—C36—H36B109.5
N4—C14—C19119.6 (4)N10—C36—H36C109.5
N4—C15—H15A109.5H36A—C36—H36C109.5
N4—C15—H15B109.5H36B—C36—H36C109.5
H15A—C15—H15B109.5O8—C37—N10119.8 (3)
N4—C15—H15C109.5O8—C37—C38125.8 (3)
H15A—C15—H15C109.5N10—C37—C38114.4 (3)
H15B—C15—H15C109.5C33—C38—C26117.6 (3)
O3—C16—N5121.6 (5)C33—C38—C37120.0 (3)
O3—C16—N4121.6 (4)C26—C38—C37122.3 (3)
N5—C16—N4116.8 (4)C11—N1—C9125.6 (4)
N5—C17—H17A109.5C11—N1—C10116.2 (4)
N5—C17—H17B109.5C9—N1—C10118.2 (3)
H17A—C17—H17B109.5C11—N2—C13123.5 (3)
N5—C17—H17C109.5C11—N2—C12114.9 (4)
H17A—C17—H17C109.5C13—N2—C12121.5 (4)
H17B—C17—H17C109.5C13—N3—C14118.3 (3)
O4—C18—N5118.2 (4)C14—N4—C16123.2 (3)
O4—C18—C19125.8 (4)C14—N4—C15121.2 (4)
N5—C18—C19116.0 (3)C16—N4—C15115.5 (4)
C14—C19—C7117.4 (3)C16—N5—C18125.0 (4)
C14—C19—C18119.4 (3)C16—N5—C17116.7 (4)
C7—C19—C18123.2 (3)C18—N5—C17118.3 (3)
C21—C20—C25122.9 (4)C30—N6—C28125.8 (3)
C21—C20—F2117.9 (4)C30—N6—C29117.7 (3)
C25—C20—F2119.2 (4)C28—N6—C29116.4 (3)
C20—C21—C22117.9 (4)C32—N7—C30122.2 (3)
C20—C21—H21121C32—N7—C31120.6 (3)
C22—C21—H21121C30—N7—C31117.1 (3)
C23—C22—C21120.7 (3)C33—N8—C32116.6 (3)
C23—C22—H22119.7C35—N9—C33122.1 (3)
C21—C22—H22119.7C35—N9—C34117.3 (3)
C24—C23—C22119.5 (3)C33—N9—C34120.6 (3)
C24—C23—C26117.7 (3)C35—N10—C37126.4 (3)
C22—C23—C26122.7 (3)C35—N10—C36117.4 (3)
C23—C24—C25120.3 (4)C37—N10—C36116.2 (3)
F1—C1—C2—C3177.2 (4)O8—C37—C38—C262.9 (6)
C6—C1—C2—C3−2.3 (7)N10—C37—C38—C26−177.3 (3)
C1—C2—C3—C41.1 (7)O2—C11—N1—C9177.7 (4)
C2—C3—C4—C50.2 (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—C10176.9 (3)
C7—C4—C5—C6177.3 (3)O1—C9—N1—C11177.3 (4)
F1—C1—C6—C5−177.5 (3)C8—C9—N1—C11−2.2 (5)
C2—C1—C6—C52.0 (6)O1—C9—N1—C10−2.3 (6)
C4—C5—C6—C1−0.6 (6)C8—C9—N1—C10178.2 (3)
C3—C4—C7—C19−97.7 (4)O2—C11—N2—C13−174.3 (4)
C5—C4—C7—C1984.5 (4)N1—C11—N2—C136.1 (5)
C3—C4—C7—C882.6 (5)O2—C11—N2—C124.2 (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—C11176.5 (3)
C4—C7—C8—C13178.8 (3)C8—C13—N2—C11−4.4 (5)
C19—C7—C8—C9179.4 (3)N3—C13—N2—C12−1.9 (5)
C4—C7—C8—C9−0.8 (5)C8—C13—N2—C12177.3 (3)
C13—C8—C9—O1−175.5 (4)N2—C13—N3—C14−178.6 (3)
C7—C8—C9—O14.2 (6)C8—C13—N3—C142.2 (5)
C13—C8—C9—N14.0 (5)N4—C14—N3—C13179.4 (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—N3178.1 (3)C19—C14—N4—C163.6 (5)
C7—C8—C13—N2179.4 (3)N3—C14—N4—C157.6 (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—C14176.1 (4)
N4—C14—C19—C7178.3 (3)N5—C16—N4—C14−2.9 (6)
N3—C14—C19—C18177.0 (3)O3—C16—N4—C15−7.5 (6)
N4—C14—C19—C18−2.8 (5)N5—C16—N4—C15173.5 (4)
C8—C7—C19—C142.5 (5)O3—C16—N5—C18−177.4 (4)
C4—C7—C19—C14−177.3 (3)N4—C16—N5—C181.6 (6)
C8—C7—C19—C18−176.4 (3)O3—C16—N5—C173.2 (6)
C4—C7—C19—C183.9 (5)N4—C16—N5—C17−177.8 (3)
O4—C18—C19—C14−177.4 (4)O4—C18—N5—C16178.0 (4)
N5—C18—C19—C141.5 (5)C19—C18—N5—C16−0.9 (5)
O4—C18—C19—C71.5 (6)O4—C18—N5—C17−2.7 (5)
N5—C18—C19—C7−179.7 (3)C19—C18—N5—C17178.4 (3)
C25—C20—C21—C220.6 (7)O6—C30—N6—C28−178.1 (3)
F2—C20—C21—C22−179.7 (4)N7—C30—N6—C280.9 (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—C29177.3 (3)
C21—C22—C23—C26177.1 (4)O5—C28—N6—C30169.1 (3)
C22—C23—C24—C250.2 (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—C29172.4 (3)
F2—C20—C25—C24179.7 (4)N8—C32—N7—C30176.0 (3)
C23—C24—C25—C200.2 (6)C27—C32—N7—C30−3.8 (5)
C24—C23—C26—C2771.1 (4)N8—C32—N7—C31−1.1 (5)
C22—C23—C26—C27−106.2 (4)C27—C32—N7—C31179.1 (3)
C24—C23—C26—C38−105.6 (4)O6—C30—N7—C32−173.9 (3)
C22—C23—C26—C3877.1 (4)N6—C30—N7—C327.1 (5)
C38—C26—C27—C322.5 (4)O6—C30—N7—C313.4 (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—C285.9 (5)C38—C33—N8—C320.6 (5)
C26—C27—C28—O513.4 (5)N7—C32—N8—C33−174.7 (3)
C32—C27—C28—O5−166.4 (3)C27—C32—N8—C335.1 (5)
C26—C27—C28—N6−166.4 (3)O7—C35—N9—C33179.6 (4)
C32—C27—C28—N613.8 (4)N10—C35—N9—C330.8 (5)
C26—C27—C32—N8−6.8 (5)O7—C35—N9—C34−1.5 (6)
C28—C27—C32—N8173.0 (3)N10—C35—N9—C34179.7 (3)
C26—C27—C32—N7173.0 (3)N8—C33—N9—C35−176.0 (3)
C28—C27—C32—N7−7.2 (5)C38—C33—N9—C353.6 (5)
N8—C33—C38—C26−4.5 (5)N8—C33—N9—C345.1 (5)
N9—C33—C38—C26176.0 (3)C38—C33—N9—C34−175.3 (4)
N8—C33—C38—C37172.5 (3)O7—C35—N10—C37179.5 (4)
N9—C33—C38—C37−7.1 (5)N9—C35—N10—C37−1.7 (6)
C27—C26—C38—C332.6 (4)O7—C35—N10—C360.6 (6)
C23—C26—C38—C33179.4 (3)N9—C35—N10—C36179.4 (3)
C27—C26—C38—C37−174.3 (3)O8—C37—N10—C35178.2 (4)
C23—C26—C38—C372.5 (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—C335.9 (5)C38—C37—N10—C36177.3 (3)
Acknowledgements top

The authors acknowledge Islamic Azad University for financial support.

references
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