organic compounds
5-Butylamino-6-(4-fluorophenyl)-7-oxo-1-p-tolyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidine-3-carbonitrile
aCollege of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China, and bDepartment of Chemistry and Life Sciences, Xianning College, Xianning 437100, People's Republic of China
*Correspondence e-mail: minghuwu@hotmail.com
In the title compound, C23H21FN6O, the dihedral angle between the fluorophenyl and pyrimidinone rings is 75.9 (1)°, and the dihedral angle between the methylphenyl and pyrazole rings is 40.3 (1)°. In the weak C—H⋯π(arene) and C—N⋯π(arene) interactions and intermolecular C—H⋯N and N—H⋯O hydrogen-bonding interactions are present.
Related literature
For background information, see: Bell et al. (1991); Zhao et al. (2006); Allerton et al. (2006).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Supporting information
10.1107/S1600536808009744/er2051sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009744/er2051Isup2.hkl
To a solution of 4-(3-cyano-5-ethoxycarbonyl-p-tolyl-1H-pyrazolyl) iminophosphorane (1.59 g, 3 mmol) in absolute anhydrous CH2Cl2, 4-fluorophenylisocyanate (3 mmol) was added at room temperature. The reaction mixture was left unstirred for 6 h at 273–278 K, whereafter a slight excess of butylamine (3.1 mmol) was added. After that, the reaction mixture was stirred for 6 h, the solution was cooled and the reaction product was recrystallized from EtOH and CH2Cl2 to give colorless crystals of the title compound in yield 93%, suitable for X-ray analysis.
All H atoms bound to C atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and included in the riding model approximation, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).Fig. 1. View of the molecule with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. The packing viewed down the b axis. Intermolecular hydrogen bonds are shown as dashed lines. |
C23H21FN6O | F(000) = 872 |
Mr = 416.46 | Dx = 1.309 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3510 reflections |
a = 11.8800 (5) Å | θ = 2.4–23.9° |
b = 9.36020 (4) Å | µ = 0.09 mm−1 |
c = 19.0053 (8) Å | T = 295 K |
β = 91.178 (1)° | Block, colourless |
V = 2112.93 (13) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 3704 independent reflections |
Radiation source: fine-focus sealed tube | 3085 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −14→14 |
Tmin = 0.973, Tmax = 0.982 | k = −11→11 |
12013 measured reflections | l = −16→22 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0811P)2 + 0.4221P] where P = (Fo2 + 2Fc2)/3 |
3704 reflections | (Δ/σ)max < 0.001 |
285 parameters | Δρmax = 0.23 e Å−3 |
1 restraint | Δρmin = −0.26 e Å−3 |
C23H21FN6O | V = 2112.93 (13) Å3 |
Mr = 416.46 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.8800 (5) Å | µ = 0.09 mm−1 |
b = 9.36020 (4) Å | T = 295 K |
c = 19.0053 (8) Å | 0.30 × 0.20 × 0.20 mm |
β = 91.178 (1)° |
Bruker SMART APEX CCD diffractometer | 3704 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 3085 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.982 | Rint = 0.031 |
12013 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 1 restraint |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.23 e Å−3 |
3704 reflections | Δρmin = −0.26 e Å−3 |
285 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. |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6274 (2) | 0.3875 (3) | 0.22154 (16) | 0.0778 (9) | |
H1A | 0.6429 | 0.3528 | 0.2683 | 0.117* | |
H1B | 0.6068 | 0.4865 | 0.2236 | 0.117* | |
H1C | 0.6934 | 0.3769 | 0.1937 | 0.117* | |
C2 | 0.53165 (19) | 0.3027 (3) | 0.18861 (12) | 0.0517 (6) | |
C3 | 0.55219 (19) | 0.1809 (3) | 0.15018 (14) | 0.0614 (7) | |
H3 | 0.6261 | 0.1512 | 0.1443 | 0.074* | |
C4 | 0.46540 (18) | 0.1021 (3) | 0.12017 (14) | 0.0552 (6) | |
H4 | 0.4809 | 0.0204 | 0.0942 | 0.066* | |
C5 | 0.35615 (17) | 0.1450 (2) | 0.12887 (11) | 0.0399 (5) | |
C6 | 0.33266 (18) | 0.2674 (2) | 0.16595 (12) | 0.0473 (6) | |
H6 | 0.2587 | 0.2978 | 0.1708 | 0.057* | |
C7 | 0.4207 (2) | 0.3443 (2) | 0.19588 (13) | 0.0525 (6) | |
H7 | 0.4049 | 0.4262 | 0.2216 | 0.063* | |
C8 | 0.18880 (17) | −0.0696 (2) | 0.01909 (11) | 0.0406 (5) | |
C9 | 0.11084 (16) | −0.0625 (2) | 0.07421 (10) | 0.0362 (5) | |
C10 | 0.16433 (16) | 0.0224 (2) | 0.12452 (11) | 0.0361 (5) | |
C11 | 0.17644 (18) | −0.1440 (3) | −0.04584 (12) | 0.0468 (6) | |
C12 | −0.03810 (16) | −0.1084 (2) | 0.14132 (11) | 0.0371 (5) | |
C13 | 0.11533 (16) | 0.0439 (2) | 0.19173 (11) | 0.0368 (5) | |
C14 | −0.04608 (16) | −0.0095 (2) | 0.26283 (10) | 0.0378 (5) | |
C15 | −0.13358 (18) | 0.0858 (2) | 0.26853 (12) | 0.0465 (5) | |
H15 | −0.1606 | 0.1347 | 0.2291 | 0.056* | |
C16 | −0.1812 (2) | 0.1083 (3) | 0.33376 (13) | 0.0533 (6) | |
H16 | −0.2413 | 0.1709 | 0.3384 | 0.064* | |
C17 | −0.1383 (2) | 0.0369 (3) | 0.39086 (12) | 0.0544 (6) | |
C18 | −0.0514 (2) | −0.0580 (3) | 0.38634 (12) | 0.0555 (6) | |
H18 | −0.0241 | −0.1056 | 0.4261 | 0.067* | |
C19 | −0.00515 (19) | −0.0814 (2) | 0.32127 (12) | 0.0481 (6) | |
H19 | 0.0538 | −0.1459 | 0.3168 | 0.058* | |
C20 | −0.19690 (18) | −0.2591 (2) | 0.10305 (12) | 0.0466 (5) | |
H20A | −0.1732 | −0.3570 | 0.1113 | 0.056* | |
H20B | −0.1764 | −0.2329 | 0.0556 | 0.056* | |
C21 | −0.32235 (19) | −0.2480 (3) | 0.11024 (13) | 0.0523 (6) | |
H21A | −0.3451 | −0.1499 | 0.1017 | 0.063* | |
H21B | −0.3416 | −0.2719 | 0.1582 | 0.063* | |
C22 | −0.3878 (2) | −0.3448 (3) | 0.06021 (15) | 0.0654 (7) | |
H22A | −0.3655 | −0.4430 | 0.0689 | 0.078* | |
H22B | −0.3684 | −0.3214 | 0.0123 | 0.078* | |
C23 | −0.5142 (2) | −0.3322 (4) | 0.0676 (2) | 0.1029 (13) | |
H23A | −0.5328 | −0.3385 | 0.1164 | 0.154* | |
H23B | −0.5507 | −0.4081 | 0.0420 | 0.154* | |
H23C | −0.5392 | −0.2419 | 0.0491 | 0.154* | |
F1 | −0.18395 (16) | 0.0621 (2) | 0.45430 (8) | 0.0869 (6) | |
N1 | 0.26695 (13) | 0.06138 (18) | 0.09789 (9) | 0.0396 (4) | |
N2 | 0.28234 (14) | 0.0051 (2) | 0.03381 (9) | 0.0437 (5) | |
N3 | 0.16543 (19) | −0.2048 (3) | −0.09756 (11) | 0.0671 (6) | |
N4 | 0.00947 (14) | −0.12733 (18) | 0.08064 (9) | 0.0386 (4) | |
N5 | 0.01053 (13) | −0.02716 (18) | 0.19646 (8) | 0.0373 (4) | |
N6 | −0.13968 (15) | −0.1649 (2) | 0.15346 (9) | 0.0452 (5) | |
H6A | −0.1566 (19) | −0.175 (3) | 0.1970 (6) | 0.054* | |
O1 | 0.15378 (12) | 0.11047 (17) | 0.24170 (8) | 0.0502 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0649 (18) | 0.080 (2) | 0.087 (2) | −0.0194 (15) | −0.0151 (16) | −0.0128 (16) |
C2 | 0.0469 (13) | 0.0553 (14) | 0.0527 (14) | −0.0113 (11) | −0.0035 (10) | 0.0014 (11) |
C3 | 0.0333 (12) | 0.0704 (17) | 0.0807 (19) | −0.0020 (11) | 0.0045 (12) | −0.0152 (14) |
C4 | 0.0386 (12) | 0.0573 (15) | 0.0698 (17) | −0.0003 (10) | 0.0073 (11) | −0.0186 (12) |
C5 | 0.0375 (11) | 0.0428 (12) | 0.0395 (12) | −0.0042 (9) | 0.0018 (9) | 0.0025 (9) |
C6 | 0.0379 (11) | 0.0435 (12) | 0.0605 (14) | 0.0020 (9) | 0.0013 (10) | 0.0014 (11) |
C7 | 0.0520 (14) | 0.0427 (13) | 0.0628 (15) | −0.0041 (10) | 0.0031 (11) | −0.0073 (11) |
C8 | 0.0373 (11) | 0.0505 (12) | 0.0340 (11) | −0.0020 (9) | 0.0000 (9) | 0.0006 (9) |
C9 | 0.0353 (10) | 0.0389 (11) | 0.0344 (11) | 0.0006 (8) | −0.0018 (8) | 0.0031 (9) |
C10 | 0.0330 (10) | 0.0376 (11) | 0.0377 (11) | 0.0011 (8) | 0.0004 (8) | 0.0013 (9) |
C11 | 0.0417 (12) | 0.0613 (14) | 0.0375 (13) | −0.0070 (10) | 0.0064 (9) | 0.0005 (11) |
C12 | 0.0357 (11) | 0.0395 (11) | 0.0359 (12) | −0.0004 (8) | −0.0031 (9) | 0.0030 (9) |
C13 | 0.0337 (10) | 0.0394 (11) | 0.0372 (11) | 0.0023 (8) | −0.0025 (8) | −0.0008 (9) |
C14 | 0.0347 (10) | 0.0422 (11) | 0.0365 (11) | −0.0046 (9) | 0.0012 (8) | −0.0023 (9) |
C15 | 0.0422 (12) | 0.0484 (13) | 0.0490 (14) | −0.0015 (10) | 0.0025 (10) | 0.0043 (10) |
C16 | 0.0468 (13) | 0.0523 (14) | 0.0615 (16) | 0.0020 (10) | 0.0162 (11) | −0.0049 (12) |
C17 | 0.0598 (15) | 0.0617 (15) | 0.0423 (14) | −0.0120 (12) | 0.0157 (11) | −0.0092 (12) |
C18 | 0.0569 (15) | 0.0720 (16) | 0.0376 (13) | −0.0013 (12) | 0.0001 (10) | 0.0037 (12) |
C19 | 0.0466 (12) | 0.0561 (14) | 0.0418 (13) | 0.0063 (10) | 0.0014 (10) | 0.0032 (10) |
C20 | 0.0452 (12) | 0.0517 (13) | 0.0430 (13) | −0.0091 (10) | −0.0007 (10) | −0.0018 (10) |
C21 | 0.0459 (13) | 0.0547 (14) | 0.0561 (15) | −0.0105 (11) | 0.0009 (11) | −0.0026 (11) |
C22 | 0.0543 (15) | 0.0717 (18) | 0.0700 (17) | −0.0164 (13) | −0.0053 (13) | −0.0101 (14) |
C23 | 0.0517 (17) | 0.104 (3) | 0.152 (3) | −0.0189 (17) | −0.0184 (19) | −0.032 (2) |
F1 | 0.0979 (12) | 0.1106 (14) | 0.0536 (10) | 0.0002 (10) | 0.0339 (9) | −0.0121 (9) |
N1 | 0.0336 (9) | 0.0448 (10) | 0.0405 (10) | −0.0028 (7) | 0.0036 (7) | −0.0026 (8) |
N2 | 0.0391 (10) | 0.0533 (11) | 0.0390 (10) | −0.0034 (8) | 0.0039 (8) | −0.0027 (8) |
N3 | 0.0729 (15) | 0.0862 (16) | 0.0425 (12) | −0.0188 (12) | 0.0066 (10) | −0.0109 (12) |
N4 | 0.0366 (9) | 0.0445 (10) | 0.0346 (10) | −0.0043 (7) | −0.0011 (7) | 0.0006 (7) |
N5 | 0.0342 (9) | 0.0461 (10) | 0.0316 (9) | −0.0027 (7) | 0.0016 (7) | −0.0008 (7) |
N6 | 0.0430 (10) | 0.0552 (11) | 0.0374 (10) | −0.0145 (8) | 0.0036 (8) | −0.0004 (9) |
O1 | 0.0453 (9) | 0.0611 (10) | 0.0442 (9) | −0.0109 (7) | 0.0015 (7) | −0.0139 (7) |
C1—C2 | 1.512 (3) | C14—C15 | 1.375 (3) |
C1—H1A | 0.9600 | C14—C19 | 1.379 (3) |
C1—H1B | 0.9600 | C14—N5 | 1.451 (3) |
C1—H1C | 0.9600 | C15—C16 | 1.389 (3) |
C2—C3 | 1.379 (3) | C15—H15 | 0.9300 |
C2—C7 | 1.384 (3) | C16—C17 | 1.364 (3) |
C3—C4 | 1.382 (3) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C17—F1 | 1.353 (3) |
C4—C5 | 1.372 (3) | C17—C18 | 1.366 (3) |
C4—H4 | 0.9300 | C18—C19 | 1.381 (3) |
C5—C6 | 1.376 (3) | C18—H18 | 0.9300 |
C5—N1 | 1.434 (3) | C19—H19 | 0.9300 |
C6—C7 | 1.382 (3) | C20—N6 | 1.460 (3) |
C6—H6 | 0.9300 | C20—C21 | 1.503 (3) |
C7—H7 | 0.9300 | C20—H20A | 0.9700 |
C8—N2 | 1.338 (3) | C20—H20B | 0.9700 |
C8—C9 | 1.414 (3) | C21—C22 | 1.516 (3) |
C8—C11 | 1.422 (3) | C21—H21A | 0.9700 |
C9—N4 | 1.356 (3) | C21—H21B | 0.9700 |
C9—C10 | 1.387 (3) | C22—C23 | 1.516 (4) |
C10—N1 | 1.379 (2) | C22—H22A | 0.9700 |
C10—C13 | 1.429 (3) | C22—H22B | 0.9700 |
C11—N3 | 1.141 (3) | C23—H23A | 0.9600 |
C12—N4 | 1.307 (3) | C23—H23B | 0.9600 |
C12—N6 | 1.342 (3) | C23—H23C | 0.9600 |
C12—N5 | 1.409 (3) | N1—N2 | 1.343 (2) |
C13—O1 | 1.217 (2) | N6—H6A | 0.861 (10) |
C13—N5 | 1.416 (3) | ||
C2—C1—H1A | 109.5 | C17—C16—H16 | 120.5 |
C2—C1—H1B | 109.5 | C15—C16—H16 | 120.5 |
H1A—C1—H1B | 109.5 | F1—C17—C16 | 118.2 (2) |
C2—C1—H1C | 109.5 | F1—C17—C18 | 119.1 (2) |
H1A—C1—H1C | 109.5 | C16—C17—C18 | 122.6 (2) |
H1B—C1—H1C | 109.5 | C17—C18—C19 | 118.3 (2) |
C3—C2—C7 | 117.7 (2) | C17—C18—H18 | 120.8 |
C3—C2—C1 | 120.9 (2) | C19—C18—H18 | 120.8 |
C7—C2—C1 | 121.4 (2) | C14—C19—C18 | 120.2 (2) |
C2—C3—C4 | 121.5 (2) | C14—C19—H19 | 119.9 |
C2—C3—H3 | 119.3 | C18—C19—H19 | 119.9 |
C4—C3—H3 | 119.3 | N6—C20—C21 | 110.36 (18) |
C5—C4—C3 | 119.6 (2) | N6—C20—H20A | 109.6 |
C5—C4—H4 | 120.2 | C21—C20—H20A | 109.6 |
C3—C4—H4 | 120.2 | N6—C20—H20B | 109.6 |
C4—C5—C6 | 120.5 (2) | C21—C20—H20B | 109.6 |
C4—C5—N1 | 118.90 (19) | H20A—C20—H20B | 108.1 |
C6—C5—N1 | 120.57 (18) | C20—C21—C22 | 113.5 (2) |
C5—C6—C7 | 119.0 (2) | C20—C21—H21A | 108.9 |
C5—C6—H6 | 120.5 | C22—C21—H21A | 108.9 |
C7—C6—H6 | 120.5 | C20—C21—H21B | 108.9 |
C6—C7—C2 | 121.8 (2) | C22—C21—H21B | 108.9 |
C6—C7—H7 | 119.1 | H21A—C21—H21B | 107.7 |
C2—C7—H7 | 119.1 | C21—C22—C23 | 113.0 (2) |
N2—C8—C9 | 111.97 (18) | C21—C22—H22A | 109.0 |
N2—C8—C11 | 120.53 (19) | C23—C22—H22A | 109.0 |
C9—C8—C11 | 127.50 (19) | C21—C22—H22B | 109.0 |
N4—C9—C10 | 126.10 (19) | C23—C22—H22B | 109.0 |
N4—C9—C8 | 129.92 (18) | H22A—C22—H22B | 107.8 |
C10—C9—C8 | 103.89 (17) | C22—C23—H23A | 109.5 |
N1—C10—C9 | 107.14 (17) | C22—C23—H23B | 109.5 |
N1—C10—C13 | 132.08 (18) | H23A—C23—H23B | 109.5 |
C9—C10—C13 | 120.51 (18) | C22—C23—H23C | 109.5 |
N3—C11—C8 | 179.1 (3) | H23A—C23—H23C | 109.5 |
N4—C12—N6 | 120.35 (18) | H23B—C23—H23C | 109.5 |
N4—C12—N5 | 123.46 (17) | N2—N1—C10 | 111.51 (16) |
N6—C12—N5 | 116.17 (18) | N2—N1—C5 | 118.25 (16) |
O1—C13—N5 | 120.49 (18) | C10—N1—C5 | 130.19 (17) |
O1—C13—C10 | 128.07 (19) | C8—N2—N1 | 105.48 (16) |
N5—C13—C10 | 111.42 (16) | C12—N4—C9 | 114.82 (17) |
C15—C14—C19 | 120.5 (2) | C12—N5—C13 | 123.64 (16) |
C15—C14—N5 | 120.46 (18) | C12—N5—C14 | 121.19 (16) |
C19—C14—N5 | 118.84 (18) | C13—N5—C14 | 115.17 (15) |
C14—C15—C16 | 119.4 (2) | C12—N6—C20 | 122.23 (18) |
C14—C15—H15 | 120.3 | C12—N6—H6A | 116.0 (16) |
C16—C15—H15 | 120.3 | C20—N6—H6A | 116.6 (16) |
C17—C16—C15 | 118.9 (2) | ||
C7—C2—C3—C4 | −0.4 (4) | N6—C20—C21—C22 | −179.1 (2) |
C1—C2—C3—C4 | 179.6 (3) | C20—C21—C22—C23 | −179.7 (3) |
C2—C3—C4—C5 | −0.3 (4) | C9—C10—N1—N2 | −0.6 (2) |
C3—C4—C5—C6 | 1.3 (4) | C13—C10—N1—N2 | 173.4 (2) |
C3—C4—C5—N1 | −179.5 (2) | C9—C10—N1—C5 | −178.14 (19) |
C4—C5—C6—C7 | −1.7 (3) | C13—C10—N1—C5 | −4.2 (4) |
N1—C5—C6—C7 | 179.2 (2) | C4—C5—N1—N2 | −38.9 (3) |
C5—C6—C7—C2 | 1.0 (4) | C6—C5—N1—N2 | 140.2 (2) |
C3—C2—C7—C6 | 0.0 (4) | C4—C5—N1—C10 | 138.4 (2) |
C1—C2—C7—C6 | −180.0 (2) | C6—C5—N1—C10 | −42.4 (3) |
N2—C8—C9—N4 | −177.1 (2) | C9—C8—N2—N1 | 0.0 (2) |
C11—C8—C9—N4 | 3.1 (4) | C11—C8—N2—N1 | 179.83 (19) |
N2—C8—C9—C10 | −0.3 (2) | C10—N1—N2—C8 | 0.4 (2) |
C11—C8—C9—C10 | 179.8 (2) | C5—N1—N2—C8 | 178.24 (17) |
N4—C9—C10—N1 | 177.48 (18) | N6—C12—N4—C9 | 178.61 (18) |
C8—C9—C10—N1 | 0.6 (2) | N5—C12—N4—C9 | 0.1 (3) |
N4—C9—C10—C13 | 2.7 (3) | C10—C9—N4—C12 | −1.8 (3) |
C8—C9—C10—C13 | −174.26 (18) | C8—C9—N4—C12 | 174.3 (2) |
N2—C8—C11—N3 | 159 (18) | N4—C12—N5—C13 | 0.7 (3) |
C9—C8—C11—N3 | −21 (18) | N6—C12—N5—C13 | −177.79 (18) |
N1—C10—C13—O1 | 3.8 (4) | N4—C12—N5—C14 | 179.94 (18) |
C9—C10—C13—O1 | 177.1 (2) | N6—C12—N5—C14 | 1.4 (3) |
N1—C10—C13—N5 | −174.8 (2) | O1—C13—N5—C12 | −178.73 (18) |
C9—C10—C13—N5 | −1.5 (3) | C10—C13—N5—C12 | 0.0 (3) |
C19—C14—C15—C16 | −0.5 (3) | O1—C13—N5—C14 | 2.0 (3) |
N5—C14—C15—C16 | −175.46 (19) | C10—C13—N5—C14 | −179.23 (16) |
C14—C15—C16—C17 | 1.2 (3) | C15—C14—N5—C12 | −78.0 (2) |
C15—C16—C17—F1 | 178.7 (2) | C19—C14—N5—C12 | 106.9 (2) |
C15—C16—C17—C18 | −1.2 (4) | C15—C14—N5—C13 | 101.2 (2) |
F1—C17—C18—C19 | −179.4 (2) | C19—C14—N5—C13 | −73.8 (2) |
C16—C17—C18—C19 | 0.4 (4) | N4—C12—N6—C20 | 5.5 (3) |
C15—C14—C19—C18 | −0.3 (3) | N5—C12—N6—C20 | −175.88 (18) |
N5—C14—C19—C18 | 174.8 (2) | C21—C20—N6—C12 | −152.0 (2) |
C17—C18—C19—C14 | 0.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6A···O1i | 0.86 (1) | 2.32 (2) | 2.904 (2) | 125 (2) |
C15—H15···N3ii | 0.93 | 2.58 | 3.449 (3) | 155 |
C19—H19···N3iii | 0.93 | 2.50 | 3.219 (3) | 134 |
C6—H6···Cg1iv | 0.93 | 2.82 | 3.671 (2) | 152 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y, −z; (iii) x, −y−1/2, z+1/2; (iv) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C23H21FN6O |
Mr | 416.46 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 11.8800 (5), 9.36020 (4), 19.0053 (8) |
β (°) | 91.178 (1) |
V (Å3) | 2112.93 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.973, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12013, 3704, 3085 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.154, 1.11 |
No. of reflections | 3704 |
No. of parameters | 285 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.26 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6A···O1i | 0.861 (10) | 2.32 (2) | 2.904 (2) | 125 (2) |
C15—H15···N3ii | 0.93 | 2.58 | 3.449 (3) | 154.9 |
C19—H19···N3iii | 0.93 | 2.50 | 3.219 (3) | 133.9 |
C6—H6···Cg1iv | 0.93 | 2.82 | 3.671 (2) | 152 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y, −z; (iii) x, −y−1/2, z+1/2; (iv) −x, y+1/2, −z+1/2. |
Acknowledgements
The authors gratefully acknowledge financial support of this work as a project of the Natural Science Foundation of Hubei Province under grant No. 2006ABA334.
References
Allerton, C. M. N., Barber, C. G., Beaumont, K. C., Brown, D. G., Cole, S. M., Ellis, D., Lane, C. A. L., Maw, G. N., Mount, N. M., Rawson, D. J., Robinson, C. M., Street, S. D. A. & Summerhill, N. W. (2006). J. Med. Chem. 49, 3581–3594. Web of Science CrossRef PubMed CAS Google Scholar
Bell, A. S., Brown, D. & Terrett, N. K. (1991). Eur. Patent 463756. Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, Y., Zhai, X., Chen, J., Guo, S. & Gong, P. (2006). Chem. Res. Chin. Univ. 22, 468–473. Web of Science CrossRef CAS Google Scholar
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Pyrazolo[4,3-d]pyrimidin-7-ones have been reported as potent and selective inhibitors of PDE5 (Bell et al., 1991; Zhao et al., 2006). Sildenafil citrate, a pyrazolo[4,3-d]pyrimidin-7-one derivative, is the first orally effective PDE5 inhibitor approved for the treatment of erectile dysfunction. Its advent has spurred significant interest in the development of additional PDE5 inhibitors (Allerton et al., 2006). Herein, the title compound as Sildenafil analog was synthesized and determined by X-ray crystal diffraction in order to find new potent PDE5 inhibitors.
In the molecule (Fig. 1), the dihedral angle between the fluorophenyl and pyrimidinon ring is 75.9 (1)°, and the dihedral angle between the methylphenyl and pyrazole ring is 40.3 (1)°. The atoms O1, N1–N6, C5, C8–C14 and C20 are nearly coplanar, and N6, C21–C23 formed a plane.
In the crystal structure, molecules are linked by weak C—H···π (arene) interactions, which connected H6 to the centroid of atoms C14–19, Cg1, (symmetry code: -x,1/2 + y,1/2 - z). In addition, the crystal structure is stablized by intermolecular N—H···O and intramolecular C—H···N hydrogen-bonding interactions (Fig. 2).