organic compounds
5-Anilino-3-benzylsulfanyl-6-(3-chloroanilino)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
aSchool of Chemistry and Chemical Engneering, University of South China, Hengyang 421001, People's Republic of China, bCollege of Mathematics and Physical, University of South China, Hunan 421001, People's Republic of China, and cInstitute of Organic Synthesis, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: hqwang2009cn@yahoo.com.cn
In the title compound, C30H23ClN6OS, the benzyl, the 3-chloroanilino, the phenyl and the anilino groups form dihedral angles of 85.95 (6), 29.63 (7), 28.55 (1) and 87.48 (6)°, respectively, with the pyrazolo[3,4-d]pyrimidine unit [maximum deviation = 0.052 (2) Å]. An intramolecular N—H⋯N hydrogen bond occurs. The features N—H⋯O hydrogen bonds.
Related literature
For similar compounds, see: Wang et al. (2004, 2008). For their applications, see: Bendich et al. (1954); Ballell et al. (2007); Holla et al. (2006). For standard bond lengths, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and Mercury (Macrae et al., 2008).
Supporting information
https://doi.org/10.1107/S1600536812037683/rn2104sup1.cif
contains datablocks I, global. DOI:Supporting information file. DOI: https://doi.org/10.1107/S1600536812037683/rn2104Isup2.mol
Supporting information file. DOI: https://doi.org/10.1107/S1600536812037683/rn2104Isup3.mol
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037683/rn2104Isup4.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812037683/rn2104Isup5.cml
To a solution of iminophosphorane (2 mmol) in dry dichloromethane (20 ml) aryl isocyanate(2 mmol) was added under nitrogen atmosphere at room temperature. After the reaction mixture was stirred for 1.5 h, 0.231 g (2.0 mmol) m-chlorophenyl isocyanate was added, and the resulting mixture was stirred for an additional 30 min. Then the solvent was removed under reduced pressure, and 25 ml anhydrous ethanol and 1.5 ml of sodium ethoxide (3 mol/L) in ethanol were added to the mixture. After 3 h of stirring at room temperature, the solution was concentrated under reduced pressure and successively cooled. The crude product was collected by filtration. After recrystallization from DMF/petroleum ether or
on silica gel, white crystals were obtained.H atoms were included in their idealized positions, with C—H = 0.96 Å, and refined using a riding model with Uiso(H) = 1.2 Ueq(C) for other H atoms.
Pyrazolo[3,4-d]pyrimidine derivatives are important heterocycles as purine analogs(Bendich et al.,1954). They are usually used due to their potency as antagonists, antifungal agents (Ballell et al., 2007; Holla et al., 2006) and agrochemicals (Wang et al., 2008). We have reported the synthesis and structure of pyrazolo[3,4-d]pyrimidin-4(5H)-one derivatives (Wang et al., 2004).
The molecule and packing diagrams of the title compound were shown in Figure 1 and 2, respectively. As shown in Fig.1, the N1=C1 and N3=C4 bonds are 1.318 (3) and 1.304 (3) Å, respectively, slightly shorter than the normal C=N bond (1.329 and 1.336 Å; Allen et al., 1987) but close to 1.314 (3) and 1.302 (3) Å in our previous report (Wang et al., 2004), and the C2=C3 distance is 1.388 (3) Å, longer than the typical C=C(1.384 Å; Allen et al., 1987). In the molecule, the N–C bonds are remarkably shorter than the normal N–C single bond(1.469 Å) and longer than the C=N double bond. The packing was stabilized by the intermolecular N–H···O hydrogen bond.
For similar compounds, see: Wang et al. (2004, 2008). For their applications, see: Bendich et al. (1954); Ballell et al. (2007); Holla et al. (2006). For standard bond lengths, see: Allen et al. (1987).
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).Fig. 1. View of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. Hydrogen bonding pattern found in the title compound |
C30H23ClN6OS | Z = 2 |
Mr = 551.05 | F(000) = 572 |
Triclinic, P1 | Dx = 1.361 Mg m−3 |
a = 10.881 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.948 (4) Å | Cell parameters from 809 reflections |
c = 12.496 (5) Å | θ = 2.6–25.6° |
α = 103.824 (7)° | µ = 0.26 mm−1 |
β = 109.725 (7)° | T = 293 K |
γ = 93.377 (7)° | Block, white |
V = 1344.7 (9) Å3 | 0.42 × 0.40 × 0.36 mm |
Bruker SMART CCD area-detector diffractometer | 5440 independent reflections |
Radiation source: fine-focus sealed tube | 3418 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
phi and ω scans | θmax = 26.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker 2000) | h = −13→9 |
Tmin = 0.771, Tmax = 1.000 | k = −13→13 |
7799 measured reflections | l = −9→15 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0437P)2 + 0.3561P] where P = (Fo2 + 2Fc2)/3 |
5440 reflections | (Δ/σ)max = 0.001 |
360 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
C30H23ClN6OS | γ = 93.377 (7)° |
Mr = 551.05 | V = 1344.7 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.881 (5) Å | Mo Kα radiation |
b = 10.948 (4) Å | µ = 0.26 mm−1 |
c = 12.496 (5) Å | T = 293 K |
α = 103.824 (7)° | 0.42 × 0.40 × 0.36 mm |
β = 109.725 (7)° |
Bruker SMART CCD area-detector diffractometer | 5440 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker 2000) | 3418 reflections with I > 2σ(I) |
Tmin = 0.771, Tmax = 1.000 | Rint = 0.022 |
7799 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.40 e Å−3 |
5440 reflections | Δρmin = −0.40 e Å−3 |
360 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 | ||
Cl1 | 0.58922 (10) | −0.29645 (7) | −0.00499 (9) | 0.0950 (3) | |
S1 | 0.84719 (7) | 0.64314 (5) | 0.33369 (6) | 0.0557 (2) | |
N1 | 0.7368 (2) | 0.41189 (16) | 0.32750 (16) | 0.0462 (5) | |
N2 | 0.71298 (19) | 0.28629 (16) | 0.25760 (16) | 0.0422 (5) | |
N3 | 0.75420 (19) | 0.16942 (15) | 0.08617 (15) | 0.0395 (4) | |
N4 | 0.84282 (18) | 0.30693 (15) | 0.00045 (15) | 0.0359 (4) | |
N5 | 0.8107 (2) | 0.08909 (17) | −0.07736 (18) | 0.0448 (5) | |
H5 | 0.844 (2) | 0.108 (2) | −0.119 (2) | 0.045 (7)* | |
N6 | 0.8716 (2) | 0.31275 (17) | −0.10020 (17) | 0.0382 (5) | |
H6 | 0.944 (2) | 0.354 (2) | −0.0795 (18) | 0.034 (6)* | |
O1 | 0.89538 (16) | 0.52346 (13) | 0.07639 (13) | 0.0454 (4) | |
C1 | 0.7947 (2) | 0.47893 (19) | 0.27824 (19) | 0.0417 (5) | |
C2 | 0.8102 (2) | 0.40058 (18) | 0.17656 (18) | 0.0374 (5) | |
C3 | 0.7579 (2) | 0.27820 (19) | 0.16756 (18) | 0.0371 (5) | |
C4 | 0.8006 (2) | 0.18745 (18) | 0.00674 (18) | 0.0359 (5) | |
C5 | 0.8535 (2) | 0.42237 (19) | 0.08658 (18) | 0.0360 (5) | |
C6 | 0.8389 (3) | 0.6721 (2) | 0.4802 (2) | 0.0571 (7) | |
H6A | 0.7510 | 0.6403 | 0.4744 | 0.068* | |
H6B | 0.9018 | 0.6285 | 0.5272 | 0.068* | |
C7 | 0.8708 (2) | 0.8136 (2) | 0.5377 (2) | 0.0438 (6) | |
C8 | 0.7750 (3) | 0.8901 (2) | 0.5120 (2) | 0.0568 (7) | |
H8 | 0.6906 | 0.8537 | 0.4584 | 0.068* | |
C9 | 0.8016 (3) | 1.0192 (3) | 0.5641 (3) | 0.0661 (8) | |
H9 | 0.7353 | 1.0691 | 0.5462 | 0.079* | |
C10 | 0.9247 (3) | 1.0737 (3) | 0.6416 (3) | 0.0691 (8) | |
H10 | 0.9423 | 1.1608 | 0.6779 | 0.083* | |
C11 | 1.0216 (3) | 1.0016 (3) | 0.6661 (3) | 0.0770 (9) | |
H11 | 1.1063 | 1.0395 | 0.7181 | 0.092* | |
C12 | 0.9953 (3) | 0.8704 (3) | 0.6138 (2) | 0.0655 (8) | |
H12 | 1.0626 | 0.8214 | 0.6307 | 0.079* | |
C13 | 0.6338 (2) | 0.1923 (2) | 0.27856 (19) | 0.0421 (5) | |
C14 | 0.5503 (3) | 0.2301 (2) | 0.3367 (2) | 0.0567 (7) | |
H14 | 0.5454 | 0.3160 | 0.3624 | 0.068* | |
C15 | 0.4731 (3) | 0.1394 (3) | 0.3569 (2) | 0.0700 (8) | |
H15 | 0.4168 | 0.1650 | 0.3969 | 0.084* | |
C16 | 0.4787 (3) | 0.0121 (3) | 0.3187 (2) | 0.0657 (8) | |
H16 | 0.4275 | −0.0482 | 0.3335 | 0.079* | |
C17 | 0.5606 (3) | −0.0250 (2) | 0.2585 (2) | 0.0613 (7) | |
H17 | 0.5632 | −0.1112 | 0.2306 | 0.074* | |
C18 | 0.6397 (3) | 0.0644 (2) | 0.2385 (2) | 0.0537 (6) | |
H18 | 0.6962 | 0.0386 | 0.1986 | 0.064* | |
C19 | 0.7924 (2) | −0.04243 (19) | −0.08586 (19) | 0.0414 (5) | |
C20 | 0.7077 (3) | −0.0968 (2) | −0.0437 (2) | 0.0488 (6) | |
H20 | 0.6589 | −0.0476 | −0.0069 | 0.059* | |
C21 | 0.6971 (3) | −0.2271 (2) | −0.0578 (2) | 0.0554 (7) | |
C22 | 0.7651 (3) | −0.3030 (2) | −0.1140 (2) | 0.0629 (8) | |
H22 | 0.7567 | −0.3900 | −0.1219 | 0.075* | |
C23 | 0.8462 (3) | −0.2473 (2) | −0.1585 (2) | 0.0628 (7) | |
H23 | 0.8912 | −0.2978 | −0.1989 | 0.075* | |
C24 | 0.8620 (3) | −0.1173 (2) | −0.1443 (2) | 0.0532 (6) | |
H24 | 0.9185 | −0.0804 | −0.1734 | 0.064* | |
C25 | 0.7690 (2) | 0.34949 (17) | −0.18724 (18) | 0.0367 (5) | |
C26 | 0.7993 (3) | 0.3826 (2) | −0.2774 (2) | 0.0466 (6) | |
H26 | 0.8847 | 0.3840 | −0.2777 | 0.056* | |
C27 | 0.7010 (3) | 0.4132 (2) | −0.3663 (2) | 0.0621 (8) | |
H27 | 0.7206 | 0.4345 | −0.4271 | 0.075* | |
C28 | 0.5748 (3) | 0.4127 (3) | −0.3663 (2) | 0.0661 (8) | |
H28 | 0.5097 | 0.4340 | −0.4264 | 0.079* | |
C29 | 0.5450 (3) | 0.3804 (2) | −0.2768 (2) | 0.0599 (7) | |
H29 | 0.4597 | 0.3804 | −0.2763 | 0.072* | |
C30 | 0.6417 (2) | 0.3480 (2) | −0.1879 (2) | 0.0454 (6) | |
H30 | 0.6210 | 0.3250 | −0.1283 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1326 (8) | 0.0500 (4) | 0.1256 (7) | −0.0044 (4) | 0.0769 (6) | 0.0270 (5) |
S1 | 0.0814 (5) | 0.0344 (3) | 0.0551 (4) | −0.0089 (3) | 0.0419 (4) | −0.0015 (3) |
N1 | 0.0592 (13) | 0.0348 (10) | 0.0453 (11) | −0.0037 (9) | 0.0270 (10) | 0.0030 (9) |
N2 | 0.0562 (13) | 0.0326 (10) | 0.0416 (11) | −0.0012 (9) | 0.0257 (10) | 0.0072 (8) |
N3 | 0.0549 (12) | 0.0273 (9) | 0.0405 (10) | 0.0031 (8) | 0.0231 (9) | 0.0092 (8) |
N4 | 0.0485 (12) | 0.0268 (9) | 0.0376 (10) | 0.0031 (8) | 0.0220 (9) | 0.0095 (8) |
N5 | 0.0684 (15) | 0.0268 (9) | 0.0482 (12) | 0.0058 (9) | 0.0333 (11) | 0.0095 (9) |
N6 | 0.0462 (13) | 0.0320 (10) | 0.0425 (11) | 0.0015 (9) | 0.0247 (10) | 0.0097 (8) |
O1 | 0.0586 (11) | 0.0292 (8) | 0.0553 (10) | −0.0024 (7) | 0.0322 (8) | 0.0093 (7) |
C1 | 0.0506 (15) | 0.0322 (11) | 0.0431 (13) | −0.0009 (10) | 0.0233 (11) | 0.0042 (10) |
C2 | 0.0441 (14) | 0.0295 (11) | 0.0390 (12) | −0.0009 (9) | 0.0190 (10) | 0.0060 (9) |
C3 | 0.0446 (14) | 0.0326 (11) | 0.0362 (12) | 0.0020 (10) | 0.0175 (10) | 0.0099 (9) |
C4 | 0.0435 (14) | 0.0272 (10) | 0.0385 (12) | 0.0043 (9) | 0.0163 (10) | 0.0100 (9) |
C5 | 0.0364 (13) | 0.0297 (11) | 0.0419 (12) | 0.0019 (9) | 0.0160 (10) | 0.0078 (9) |
C6 | 0.081 (2) | 0.0429 (14) | 0.0478 (15) | −0.0009 (13) | 0.0318 (14) | 0.0046 (11) |
C7 | 0.0543 (16) | 0.0395 (12) | 0.0403 (13) | 0.0015 (11) | 0.0266 (12) | 0.0035 (10) |
C8 | 0.0528 (17) | 0.0561 (16) | 0.0603 (16) | 0.0026 (13) | 0.0232 (13) | 0.0114 (13) |
C9 | 0.074 (2) | 0.0498 (16) | 0.085 (2) | 0.0168 (15) | 0.0418 (18) | 0.0178 (15) |
C10 | 0.087 (2) | 0.0399 (14) | 0.087 (2) | −0.0006 (16) | 0.0523 (19) | 0.0005 (14) |
C11 | 0.061 (2) | 0.0630 (19) | 0.083 (2) | −0.0084 (16) | 0.0222 (17) | −0.0132 (16) |
C12 | 0.0561 (18) | 0.0586 (17) | 0.0715 (19) | 0.0141 (14) | 0.0196 (15) | 0.0030 (14) |
C13 | 0.0484 (15) | 0.0421 (12) | 0.0358 (12) | −0.0045 (11) | 0.0161 (11) | 0.0122 (10) |
C14 | 0.0707 (19) | 0.0505 (15) | 0.0511 (15) | −0.0058 (13) | 0.0332 (14) | 0.0051 (12) |
C15 | 0.076 (2) | 0.077 (2) | 0.0628 (18) | −0.0123 (16) | 0.0422 (16) | 0.0110 (15) |
C16 | 0.074 (2) | 0.0634 (18) | 0.0602 (17) | −0.0176 (15) | 0.0256 (15) | 0.0226 (14) |
C17 | 0.077 (2) | 0.0452 (14) | 0.0671 (18) | −0.0042 (14) | 0.0309 (16) | 0.0218 (13) |
C18 | 0.0669 (18) | 0.0450 (14) | 0.0590 (16) | 0.0046 (12) | 0.0314 (14) | 0.0204 (12) |
C19 | 0.0525 (15) | 0.0284 (11) | 0.0404 (13) | 0.0054 (10) | 0.0145 (11) | 0.0079 (10) |
C20 | 0.0653 (17) | 0.0320 (12) | 0.0514 (14) | 0.0056 (11) | 0.0260 (13) | 0.0089 (11) |
C21 | 0.0706 (19) | 0.0365 (13) | 0.0586 (16) | −0.0001 (12) | 0.0230 (14) | 0.0150 (12) |
C22 | 0.086 (2) | 0.0288 (12) | 0.0727 (19) | 0.0135 (13) | 0.0263 (17) | 0.0151 (13) |
C23 | 0.075 (2) | 0.0366 (13) | 0.0789 (19) | 0.0184 (13) | 0.0331 (16) | 0.0098 (13) |
C24 | 0.0639 (18) | 0.0365 (13) | 0.0624 (16) | 0.0082 (12) | 0.0292 (14) | 0.0103 (12) |
C25 | 0.0520 (15) | 0.0214 (10) | 0.0363 (12) | 0.0018 (9) | 0.0186 (11) | 0.0046 (9) |
C26 | 0.0625 (17) | 0.0385 (12) | 0.0442 (14) | 0.0022 (11) | 0.0292 (13) | 0.0083 (11) |
C27 | 0.088 (2) | 0.0571 (16) | 0.0436 (15) | 0.0016 (15) | 0.0250 (15) | 0.0192 (13) |
C28 | 0.075 (2) | 0.0660 (18) | 0.0525 (17) | 0.0097 (16) | 0.0115 (15) | 0.0254 (14) |
C29 | 0.0521 (17) | 0.0617 (17) | 0.0612 (17) | 0.0069 (13) | 0.0148 (14) | 0.0173 (14) |
C30 | 0.0495 (16) | 0.0426 (13) | 0.0473 (14) | 0.0013 (11) | 0.0214 (12) | 0.0140 (11) |
Cl1—C21 | 1.746 (3) | C12—H12 | 0.9300 |
S1—C1 | 1.748 (2) | C13—C14 | 1.367 (3) |
S1—C6 | 1.816 (2) | C13—C18 | 1.383 (3) |
N1—C1 | 1.318 (3) | C14—C15 | 1.386 (3) |
N1—N2 | 1.397 (2) | C14—H14 | 0.9300 |
N2—C3 | 1.357 (3) | C15—C16 | 1.373 (4) |
N2—C13 | 1.430 (3) | C15—H15 | 0.9300 |
N3—C4 | 1.304 (3) | C16—C17 | 1.369 (4) |
N3—C3 | 1.357 (3) | C16—H16 | 0.9300 |
N4—C4 | 1.389 (2) | C17—C18 | 1.387 (3) |
N4—N6 | 1.409 (2) | C17—H17 | 0.9300 |
N4—C5 | 1.420 (3) | C18—H18 | 0.9300 |
N5—C4 | 1.351 (3) | C19—C20 | 1.376 (3) |
N5—C19 | 1.415 (3) | C19—C24 | 1.392 (3) |
N5—H5 | 0.79 (2) | C20—C21 | 1.388 (3) |
N6—C25 | 1.426 (3) | C20—H20 | 0.9300 |
N6—H6 | 0.81 (2) | C21—C22 | 1.369 (4) |
O1—C5 | 1.223 (2) | C22—C23 | 1.375 (4) |
C1—C2 | 1.421 (3) | C22—H22 | 0.9300 |
C2—C3 | 1.388 (3) | C23—C24 | 1.384 (3) |
C2—C5 | 1.420 (3) | C23—H23 | 0.9300 |
C6—C7 | 1.508 (3) | C24—H24 | 0.9300 |
C6—H6A | 0.9700 | C25—C30 | 1.381 (3) |
C6—H6B | 0.9700 | C25—C26 | 1.393 (3) |
C7—C12 | 1.369 (4) | C26—C27 | 1.382 (4) |
C7—C8 | 1.377 (3) | C26—H26 | 0.9300 |
C8—C9 | 1.375 (4) | C27—C28 | 1.372 (4) |
C8—H8 | 0.9300 | C27—H27 | 0.9300 |
C9—C10 | 1.357 (4) | C28—C29 | 1.379 (4) |
C9—H9 | 0.9300 | C28—H28 | 0.9300 |
C10—C11 | 1.351 (4) | C29—C30 | 1.382 (3) |
C10—H10 | 0.9300 | C29—H29 | 0.9300 |
C11—C12 | 1.396 (4) | C30—H30 | 0.9300 |
C11—H11 | 0.9300 | ||
C1—S1—C6 | 101.17 (11) | C14—C13—C18 | 120.3 (2) |
C1—N1—N2 | 105.43 (17) | C14—C13—N2 | 119.3 (2) |
C3—N2—N1 | 110.80 (16) | C18—C13—N2 | 120.4 (2) |
C3—N2—C13 | 129.75 (18) | C13—C14—C15 | 119.5 (2) |
N1—N2—C13 | 118.85 (17) | C13—C14—H14 | 120.2 |
C4—N3—C3 | 113.84 (17) | C15—C14—H14 | 120.2 |
C4—N4—N6 | 117.28 (16) | C16—C15—C14 | 120.9 (3) |
C4—N4—C5 | 123.97 (17) | C16—C15—H15 | 119.6 |
N6—N4—C5 | 118.71 (15) | C14—C15—H15 | 119.6 |
C4—N5—C19 | 128.2 (2) | C17—C16—C15 | 119.1 (2) |
C4—N5—H5 | 115.2 (17) | C17—C16—H16 | 120.4 |
C19—N5—H5 | 115.4 (17) | C15—C16—H16 | 120.4 |
N4—N6—C25 | 114.04 (18) | C16—C17—C18 | 120.8 (3) |
N4—N6—H6 | 109.4 (15) | C16—C17—H17 | 119.6 |
C25—N6—H6 | 114.9 (15) | C18—C17—H17 | 119.6 |
N1—C1—C2 | 111.45 (18) | C13—C18—C17 | 119.3 (2) |
N1—C1—S1 | 123.62 (16) | C13—C18—H18 | 120.4 |
C2—C1—S1 | 124.93 (16) | C17—C18—H18 | 120.4 |
C3—C2—C5 | 119.40 (19) | C20—C19—C24 | 120.6 (2) |
C3—C2—C1 | 105.10 (18) | C20—C19—N5 | 123.2 (2) |
C5—C2—C1 | 135.25 (19) | C24—C19—N5 | 116.2 (2) |
N3—C3—N2 | 125.70 (18) | C19—C20—C21 | 118.1 (2) |
N3—C3—C2 | 127.08 (19) | C19—C20—H20 | 120.9 |
N2—C3—C2 | 107.21 (18) | C21—C20—H20 | 120.9 |
N3—C4—N5 | 121.72 (19) | C22—C21—C20 | 122.6 (2) |
N3—C4—N4 | 123.69 (19) | C22—C21—Cl1 | 119.16 (19) |
N5—C4—N4 | 114.59 (19) | C20—C21—Cl1 | 118.2 (2) |
O1—C5—C2 | 128.6 (2) | C21—C22—C23 | 118.3 (2) |
O1—C5—N4 | 119.93 (19) | C21—C22—H22 | 120.9 |
C2—C5—N4 | 111.51 (17) | C23—C22—H22 | 120.9 |
C7—C6—S1 | 108.09 (16) | C22—C23—C24 | 121.1 (2) |
C7—C6—H6A | 110.1 | C22—C23—H23 | 119.4 |
S1—C6—H6A | 110.1 | C24—C23—H23 | 119.4 |
C7—C6—H6B | 110.1 | C23—C24—C19 | 119.2 (2) |
S1—C6—H6B | 110.1 | C23—C24—H24 | 120.4 |
H6A—C6—H6B | 108.4 | C19—C24—H24 | 120.4 |
C12—C7—C8 | 118.1 (2) | C30—C25—C26 | 119.7 (2) |
C12—C7—C6 | 121.6 (2) | C30—C25—N6 | 122.8 (2) |
C8—C7—C6 | 120.3 (2) | C26—C25—N6 | 117.5 (2) |
C9—C8—C7 | 121.3 (3) | C27—C26—C25 | 119.2 (2) |
C9—C8—H8 | 119.3 | C27—C26—H26 | 120.4 |
C7—C8—H8 | 119.3 | C25—C26—H26 | 120.4 |
C10—C9—C8 | 119.9 (3) | C28—C27—C26 | 121.0 (2) |
C10—C9—H9 | 120.1 | C28—C27—H27 | 119.5 |
C8—C9—H9 | 120.1 | C26—C27—H27 | 119.5 |
C11—C10—C9 | 120.1 (3) | C27—C28—C29 | 119.8 (3) |
C11—C10—H10 | 120.0 | C27—C28—H28 | 120.1 |
C9—C10—H10 | 120.0 | C29—C28—H28 | 120.1 |
C10—C11—C12 | 120.3 (3) | C28—C29—C30 | 120.0 (3) |
C10—C11—H11 | 119.9 | C28—C29—H29 | 120.0 |
C12—C11—H11 | 119.9 | C30—C29—H29 | 120.0 |
C7—C12—C11 | 120.3 (3) | C25—C30—C29 | 120.3 (2) |
C7—C12—H12 | 119.9 | C25—C30—H30 | 119.8 |
C11—C12—H12 | 119.9 | C29—C30—H30 | 119.8 |
C1—N1—N2—C3 | 0.7 (3) | C6—C7—C8—C9 | 179.4 (2) |
C1—N1—N2—C13 | −171.3 (2) | C7—C8—C9—C10 | 0.7 (4) |
C4—N4—N6—C25 | 100.4 (2) | C8—C9—C10—C11 | 1.1 (4) |
C5—N4—N6—C25 | −77.3 (2) | C9—C10—C11—C12 | −1.3 (5) |
N2—N1—C1—C2 | 0.0 (3) | C8—C7—C12—C11 | 2.0 (4) |
N2—N1—C1—S1 | −179.17 (17) | C6—C7—C12—C11 | −179.6 (2) |
C6—S1—C1—N1 | 13.9 (2) | C10—C11—C12—C7 | −0.3 (5) |
C6—S1—C1—C2 | −165.1 (2) | C3—N2—C13—C14 | −149.5 (2) |
N1—C1—C2—C3 | −0.6 (3) | N1—N2—C13—C14 | 20.7 (3) |
S1—C1—C2—C3 | 178.52 (17) | C3—N2—C13—C18 | 29.3 (4) |
N1—C1—C2—C5 | 173.3 (2) | N1—N2—C13—C18 | −160.5 (2) |
S1—C1—C2—C5 | −7.5 (4) | C18—C13—C14—C15 | 1.0 (4) |
C4—N3—C3—N2 | 178.3 (2) | N2—C13—C14—C15 | 179.8 (2) |
C4—N3—C3—C2 | −3.2 (3) | C13—C14—C15—C16 | −0.4 (4) |
N1—N2—C3—N3 | 177.6 (2) | C14—C15—C16—C17 | −0.9 (4) |
C13—N2—C3—N3 | −11.5 (4) | C15—C16—C17—C18 | 1.6 (4) |
N1—N2—C3—C2 | −1.1 (3) | C14—C13—C18—C17 | −0.3 (4) |
C13—N2—C3—C2 | 169.7 (2) | N2—C13—C18—C17 | −179.1 (2) |
C5—C2—C3—N3 | 7.2 (4) | C16—C17—C18—C13 | −1.0 (4) |
C1—C2—C3—N3 | −177.7 (2) | C4—N5—C19—C20 | 30.2 (4) |
C5—C2—C3—N2 | −174.1 (2) | C4—N5—C19—C24 | −152.2 (2) |
C1—C2—C3—N2 | 1.0 (3) | C24—C19—C20—C21 | 2.0 (4) |
C3—N3—C4—N5 | 176.6 (2) | N5—C19—C20—C21 | 179.5 (2) |
C3—N3—C4—N4 | −3.8 (3) | C19—C20—C21—C22 | −1.5 (4) |
C19—N5—C4—N3 | −9.2 (4) | C19—C20—C21—Cl1 | −179.75 (19) |
C19—N5—C4—N4 | 171.1 (2) | C20—C21—C22—C23 | −0.4 (4) |
N6—N4—C4—N3 | −170.6 (2) | Cl1—C21—C22—C23 | 177.8 (2) |
C5—N4—C4—N3 | 6.9 (3) | C21—C22—C23—C24 | 1.8 (4) |
N6—N4—C4—N5 | 9.1 (3) | C22—C23—C24—C19 | −1.3 (4) |
C5—N4—C4—N5 | −173.4 (2) | C20—C19—C24—C23 | −0.7 (4) |
C3—C2—C5—O1 | 175.9 (2) | N5—C19—C24—C23 | −178.3 (2) |
C1—C2—C5—O1 | 2.6 (5) | N4—N6—C25—C30 | −15.6 (3) |
C3—C2—C5—N4 | −3.7 (3) | N4—N6—C25—C26 | 167.26 (17) |
C1—C2—C5—N4 | −177.0 (2) | C30—C25—C26—C27 | −0.1 (3) |
C4—N4—C5—O1 | 177.8 (2) | N6—C25—C26—C27 | 177.1 (2) |
N6—N4—C5—O1 | −4.7 (3) | C25—C26—C27—C28 | 0.6 (4) |
C4—N4—C5—C2 | −2.6 (3) | C26—C27—C28—C29 | −0.4 (4) |
N6—N4—C5—C2 | 174.89 (19) | C27—C28—C29—C30 | −0.4 (4) |
C1—S1—C6—C7 | −175.34 (19) | C26—C25—C30—C29 | −0.7 (3) |
S1—C6—C7—C12 | −96.8 (3) | N6—C25—C30—C29 | −177.8 (2) |
S1—C6—C7—C8 | 81.5 (3) | C28—C29—C30—C25 | 0.9 (4) |
C12—C7—C8—C9 | −2.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···N6 | 0.79 (2) | 2.19 (2) | 2.605 (3) | 114 (2) |
N6—H6···O1i | 0.81 (2) | 2.12 (2) | 2.904 (3) | 162 (2) |
Symmetry code: (i) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C30H23ClN6OS |
Mr | 551.05 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.881 (5), 10.948 (4), 12.496 (5) |
α, β, γ (°) | 103.824 (7), 109.725 (7), 93.377 (7) |
V (Å3) | 1344.7 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.42 × 0.40 × 0.36 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker 2000) |
Tmin, Tmax | 0.771, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7799, 5440, 3418 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.114, 1.01 |
No. of reflections | 5440 |
No. of parameters | 360 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.40, −0.40 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···N6 | 0.79 (2) | 2.19 (2) | 2.605 (3) | 114 (2) |
N6—H6···O1i | 0.81 (2) | 2.12 (2) | 2.904 (3) | 162 (2) |
Symmetry code: (i) −x+2, −y+1, −z. |
Acknowledgements
We gratefully acknowledge the service provided by the X-ray facility at the Department of Chemistry and Chemical Engineering, Hengyang Normal University. Financial support of this work by the National Science Foundation (No. 11175080) and by the Natural Science Fund of Hunan Province (No. 10 J J6025) is gratefully acknowledged.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Pyrazolo[3,4-d]pyrimidine derivatives are important heterocycles as purine analogs(Bendich et al.,1954). They are usually used due to their potency as antagonists, antifungal agents (Ballell et al., 2007; Holla et al., 2006) and agrochemicals (Wang et al., 2008). We have reported the synthesis and structure of pyrazolo[3,4-d]pyrimidin-4(5H)-one derivatives (Wang et al., 2004).
The molecule and packing diagrams of the title compound were shown in Figure 1 and 2, respectively. As shown in Fig.1, the N1=C1 and N3=C4 bonds are 1.318 (3) and 1.304 (3) Å, respectively, slightly shorter than the normal C=N bond (1.329 and 1.336 Å; Allen et al., 1987) but close to 1.314 (3) and 1.302 (3) Å in our previous report (Wang et al., 2004), and the C2=C3 distance is 1.388 (3) Å, longer than the typical C=C(1.384 Å; Allen et al., 1987). In the molecule, the N–C bonds are remarkably shorter than the normal N–C single bond(1.469 Å) and longer than the C=N double bond. The packing was stabilized by the intermolecular N–H···O hydrogen bond.