Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038640/wk2068sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038640/wk2068Isup2.hkl |
CCDC reference: 660315
The synthetic route is depicted in Scheme 1. For the synthesis of I, 5-carbethoxy-2,6-dimethylpyridine-3-carboxhydrazide (0.47 g, 2 mmol) was dissolved in anhydrous ethanol(5 ml) in the presence of carbon bisulfide (0.23 g, 3 mmol) and potassium hydroxide (0.17 g, 3 mmol). The mixture was stirred at room temperature for 4 h. After removal of the solvent, hydrazine hydrate was added as solvent, heated and stirred under reflux for 3 h. After cooling to room temperature, the mixture was neutralized with dilute hydrochloric acid. The precipitate formed was filtered and washed with water. A colorless solid was obtained and directly used for next step without further purification. The obtained product (0.28 g, 1 mmol) and acetylacetone (0.1 g, 1 mmol) were put together in chloroform (5 ml) with hydrochloric acid as catalyst. The mixture was heated to reflux for 3 h, cooled to room temperature and then solvent removed. The crude product was filtered, washed with water and dried. It was recrystallized from ethanol to give a colorless compound in a yield of 76% (m. p. 414 K– 415 K). IR(ν, cm-1): 3302 (NH), 3097 (pyridine CH), 2925 (CH), 1699 (C=O), 1603–1481 (C=C, C=N), 1338 (C=S); 1H-NMR (500 MHz, DMSO-d6): δ 14.03 (s, 1H, triazole NH), 8.06 (s, 1H, pyridine CH), 6.32 (s, 1H, pyrazole CH), 5.60 (s, 1H, triazole NH), 2.60 (s, 3H, pyridine CH), 2.53 (s, 3H, pyridine CH), 2.39 (s, 3H, pyrazole CH), 2.11(s, 3H, pyrazole CH); Elemental analysis, required for C15H17N7OS: C 52.46, H 4.99, N 28.55%; Found: C 52.33, H 4.87, N 28.65%. Single crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation at room temperature.
All H atoms were placed in calculated positions, with C—H=0.93–0.96 Å; N—H=0.86 Å, and included in the final cycles of refinement using a riding model,Uiso(H) = 1.2Ueq(C).
Nitrogen-containing heterocycles compounds are well known natural products moieties which represent interesting biological activities and pharmacological properties (Pandeya et al., 2000; Soudi et al., 2005). For example, the 1,2,4-triazole nucleus with the nitrogen-bridged heterocycles always show antibacterial (Holla & Kalluraya, 1988) and antifungal (Prasad et al., 1989) properties. In addition, the substituted 1,2,4-triazol is a well established N-donor heterocyclic ligand (Elwahy & Abbas, 2000). More recently, it was reported that 1,2,4-triazole derivatives complexed with metal have higher biological activity (Tardito et al., 2007). Further more, the substituted 3,5-Dimethylpyrazoles contribute significant activities to diabetes (Soliman & Darwish,1983). These useful applications for the important class of nitrogen-containing heterocycles attracted our attention. Here, we report the synthesis and structure of a new multi-heterocyclic compound.
In the molecule of the title compound, (I), (Fig. 1), the C1—N2, C2—N3 bond distances [average =1.317 (3) Å] and N2—N3 bond distance [1.369 (3) Å] are in good agreement with those found for structures containing the 1,2,4-trizole ring Özbey et al., 2000; Bruno et al., 2003). The C=S double bond [1.663 (3) Å] is equal to the corresponding double bond (Xue et al., 2004). In the pyrazole ring, the bond distances between atoms are similar with those in the literature (Yang & Liu, 2005).
It is interesting to find that the three rings are not coplanar, due to steric hinderance. The angle between triazole plane and pyridine plane is 28.90 (3)°, whereas the angle between pyrazole plane and pyridine plane is 53.26 (9)°. Furthermore, the planes of triazole and pyrazole form a dihedral angle 55.55 (2)°. As a result of the torsional angle of the title compound, the steric hinderance has been reduced that make the compound more stable.
For general backgroud, see: Soliman & Darwish (1983); Holla & Kalluraya (1988); Prasad et al. (1989); Elwahy & Abbas (2000); Pandeya et al. (2000); Soudi et al. (2005); Tardito et al. (2007). For related literature, see: Özbey et al. (2000); Bruno et al. (2003); Xue et al. (2004); Yang & Liu (2005).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C15H17N7OS | Z = 2 |
Mr = 343.42 | F(000) = 360 |
Triclinic, P1 | Dx = 1.390 Mg m−3 |
a = 8.039 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.428 (5) Å | Cell parameters from 1268 reflections |
c = 12.391 (8) Å | θ = 2.7–23.5° |
α = 102.186 (7)° | µ = 0.22 mm−1 |
β = 90.633 (8)° | T = 273 K |
γ = 90.074 (8)° | Block, colorless |
V = 820.5 (9) Å3 | 0.20 × 0.20 × 0.15 mm |
Bruker APEX II CCD area-detector diffractometer | 2861 independent reflections |
Radiation source: fine-focus sealed tube | 2142 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 25.1°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→9 |
Tmin = 0.958, Tmax = 0.968 | k = −10→9 |
4304 measured reflections | l = −14→14 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0567P)2 + 0.5239P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2861 reflections | Δρmax = 0.38 e Å−3 |
222 parameters | Δρmin = −0.45 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.004 (3) |
C15H17N7OS | γ = 90.074 (8)° |
Mr = 343.42 | V = 820.5 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.039 (5) Å | Mo Kα radiation |
b = 8.428 (5) Å | µ = 0.22 mm−1 |
c = 12.391 (8) Å | T = 273 K |
α = 102.186 (7)° | 0.20 × 0.20 × 0.15 mm |
β = 90.633 (8)° |
Bruker APEX II CCD area-detector diffractometer | 2861 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2142 reflections with I > 2σ(I) |
Tmin = 0.958, Tmax = 0.968 | Rint = 0.018 |
4304 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.38 e Å−3 |
2861 reflections | Δρmin = −0.45 e Å−3 |
222 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 basedon 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 | ||
S1 | 0.43077 (10) | 0.93706 (11) | −0.18895 (7) | 0.0538 (3) | |
C1 | 0.2477 (4) | 0.8830 (3) | −0.1465 (2) | 0.0384 (6) | |
C2 | 0.0464 (3) | 0.7909 (3) | −0.0528 (2) | 0.0351 (6) | |
C3 | −0.0417 (3) | 0.7246 (3) | 0.0307 (2) | 0.0348 (6) | |
C4 | −0.1962 (3) | 0.6475 (3) | 0.0077 (2) | 0.0369 (6) | |
C5 | −0.2259 (4) | 0.6266 (3) | 0.1905 (2) | 0.0424 (7) | |
C6 | −0.0675 (3) | 0.6903 (3) | 0.2172 (2) | 0.0369 (6) | |
C7 | 0.0229 (3) | 0.7418 (3) | 0.1367 (2) | 0.0364 (6) | |
H7 | 0.1275 | 0.7882 | 0.1537 | 0.044* | |
C8 | 0.0107 (3) | 0.6855 (4) | 0.3260 (2) | 0.0410 (7) | |
C9 | 0.1963 (3) | 1.0647 (4) | 0.4101 (2) | 0.0427 (7) | |
C10 | 0.2723 (4) | 0.9843 (4) | 0.4868 (2) | 0.0470 (7) | |
H10 | 0.3484 | 1.0294 | 0.5418 | 0.056* | |
C11 | 0.2150 (4) | 0.8312 (4) | 0.4659 (2) | 0.0444 (7) | |
C12 | 0.2215 (4) | 1.2347 (4) | 0.3972 (3) | 0.0566 (9) | |
H12A | 0.1676 | 1.2492 | 0.3305 | 0.085* | |
H12B | 0.3384 | 1.2562 | 0.3935 | 0.085* | |
H12C | 0.1749 | 1.3083 | 0.4592 | 0.085* | |
C13 | 0.2588 (5) | 0.6943 (4) | 0.5193 (3) | 0.0661 (10) | |
H13A | 0.3405 | 0.7300 | 0.5764 | 0.099* | |
H13B | 0.3031 | 0.6065 | 0.4651 | 0.099* | |
H13C | 0.1609 | 0.6581 | 0.5509 | 0.099* | |
C14 | −0.3432 (4) | 0.5825 (5) | 0.2724 (3) | 0.0671 (10) | |
H14A | −0.4510 | 0.6267 | 0.2629 | 0.101* | |
H14B | −0.3025 | 0.6259 | 0.3459 | 0.101* | |
H14C | −0.3513 | 0.4664 | 0.2611 | 0.101* | |
C15 | −0.2747 (4) | 0.6067 (4) | −0.1048 (2) | 0.0465 (7) | |
H15A | −0.3550 | 0.5214 | −0.1076 | 0.070* | |
H15B | −0.1906 | 0.5714 | −0.1588 | 0.070* | |
H15C | −0.3291 | 0.7010 | −0.1201 | 0.070* | |
N1 | 0.2156 (3) | 0.8125 (3) | −0.05885 (17) | 0.0360 (5) | |
N2 | 0.0964 (3) | 0.8979 (3) | −0.18831 (19) | 0.0436 (6) | |
H2 | 0.0793 | 0.9383 | −0.2456 | 0.052* | |
N3 | −0.0292 (3) | 0.8433 (3) | −0.13175 (19) | 0.0433 (6) | |
N4 | 0.3343 (3) | 0.7712 (3) | 0.01276 (19) | 0.0471 (7) | |
H4A | 0.4379 | 0.7897 | 0.0038 | 0.057* | |
H4B | 0.3041 | 0.7271 | 0.0661 | 0.057* | |
N5 | −0.2849 (3) | 0.6039 (3) | 0.08698 (19) | 0.0425 (6) | |
N6 | 0.1045 (3) | 0.8203 (3) | 0.37803 (17) | 0.0382 (6) | |
N7 | 0.0934 (3) | 0.9668 (3) | 0.34468 (18) | 0.0394 (6) | |
O1 | −0.0008 (3) | 0.5692 (3) | 0.36724 (18) | 0.0606 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0503 (5) | 0.0658 (6) | 0.0487 (5) | −0.0140 (4) | 0.0003 (4) | 0.0197 (4) |
C1 | 0.0490 (17) | 0.0332 (15) | 0.0329 (14) | −0.0039 (12) | −0.0013 (12) | 0.0069 (11) |
C2 | 0.0382 (15) | 0.0368 (15) | 0.0301 (13) | 0.0014 (12) | −0.0031 (11) | 0.0064 (11) |
C3 | 0.0357 (14) | 0.0340 (15) | 0.0346 (14) | 0.0017 (11) | −0.0029 (11) | 0.0071 (11) |
C4 | 0.0384 (15) | 0.0350 (15) | 0.0367 (14) | 0.0014 (12) | −0.0046 (12) | 0.0063 (12) |
C5 | 0.0469 (17) | 0.0422 (17) | 0.0374 (15) | −0.0078 (13) | −0.0011 (13) | 0.0066 (12) |
C6 | 0.0413 (15) | 0.0354 (15) | 0.0337 (14) | −0.0041 (12) | −0.0037 (12) | 0.0067 (12) |
C7 | 0.0350 (15) | 0.0350 (15) | 0.0382 (15) | −0.0017 (11) | −0.0029 (12) | 0.0056 (12) |
C8 | 0.0424 (16) | 0.0458 (17) | 0.0355 (15) | −0.0056 (13) | −0.0022 (12) | 0.0102 (13) |
C9 | 0.0418 (16) | 0.0470 (17) | 0.0372 (15) | −0.0033 (13) | 0.0004 (13) | 0.0045 (13) |
C10 | 0.0452 (17) | 0.0539 (19) | 0.0400 (16) | −0.0069 (14) | −0.0110 (13) | 0.0062 (14) |
C11 | 0.0431 (17) | 0.0540 (19) | 0.0372 (15) | −0.0027 (14) | −0.0064 (13) | 0.0121 (14) |
C12 | 0.070 (2) | 0.0453 (19) | 0.0527 (19) | −0.0090 (16) | −0.0065 (16) | 0.0070 (15) |
C13 | 0.073 (2) | 0.070 (2) | 0.062 (2) | −0.0075 (19) | −0.0284 (18) | 0.0305 (18) |
C14 | 0.059 (2) | 0.094 (3) | 0.0483 (19) | −0.032 (2) | −0.0001 (16) | 0.0162 (19) |
C15 | 0.0461 (17) | 0.0526 (19) | 0.0397 (16) | −0.0055 (14) | −0.0110 (13) | 0.0077 (14) |
N1 | 0.0368 (13) | 0.0366 (13) | 0.0350 (12) | −0.0020 (10) | −0.0022 (10) | 0.0082 (10) |
N2 | 0.0469 (14) | 0.0512 (15) | 0.0368 (13) | −0.0003 (11) | −0.0021 (11) | 0.0186 (11) |
N3 | 0.0403 (13) | 0.0511 (15) | 0.0415 (13) | 0.0020 (11) | −0.0001 (11) | 0.0167 (11) |
N4 | 0.0328 (13) | 0.0736 (18) | 0.0436 (14) | −0.0076 (12) | −0.0081 (10) | 0.0323 (13) |
N5 | 0.0396 (13) | 0.0462 (15) | 0.0405 (13) | −0.0066 (11) | −0.0042 (10) | 0.0068 (11) |
N6 | 0.0417 (13) | 0.0418 (14) | 0.0324 (12) | −0.0034 (10) | −0.0047 (10) | 0.0106 (10) |
N7 | 0.0439 (14) | 0.0383 (13) | 0.0370 (12) | −0.0008 (10) | −0.0027 (10) | 0.0106 (10) |
O1 | 0.0802 (17) | 0.0545 (14) | 0.0542 (13) | −0.0188 (12) | −0.0156 (12) | 0.0284 (11) |
S1—C1 | 1.663 (3) | C10—H10 | 0.9300 |
C1—N2 | 1.333 (4) | C11—N6 | 1.385 (3) |
C1—N1 | 1.370 (3) | C11—C13 | 1.487 (4) |
C2—N3 | 1.301 (3) | C12—H12A | 0.9600 |
C2—N1 | 1.377 (3) | C12—H12B | 0.9600 |
C2—C3 | 1.463 (4) | C12—H12C | 0.9600 |
C3—C7 | 1.386 (4) | C13—H13A | 0.9600 |
C3—C4 | 1.400 (4) | C13—H13B | 0.9600 |
C4—N5 | 1.333 (4) | C13—H13C | 0.9600 |
C4—C15 | 1.495 (4) | C14—H14A | 0.9600 |
C5—N5 | 1.338 (4) | C14—H14B | 0.9600 |
C5—C6 | 1.390 (4) | C14—H14C | 0.9600 |
C5—C14 | 1.496 (4) | C15—H15A | 0.9600 |
C6—C7 | 1.382 (4) | C15—H15B | 0.9600 |
C6—C8 | 1.490 (4) | C15—H15C | 0.9600 |
C7—H7 | 0.9300 | N1—N4 | 1.390 (3) |
C8—O1 | 1.201 (3) | N2—N3 | 1.369 (3) |
C8—N6 | 1.398 (4) | N2—H2 | 0.8600 |
C9—N7 | 1.313 (3) | N4—H4A | 0.8600 |
C9—C10 | 1.412 (4) | N4—H4B | 0.8600 |
C9—C12 | 1.489 (4) | N6—N7 | 1.385 (3) |
C10—C11 | 1.341 (4) | ||
N2—C1—N1 | 102.8 (2) | C9—C12—H12C | 109.5 |
N2—C1—S1 | 129.0 (2) | H12A—C12—H12C | 109.5 |
N1—C1—S1 | 128.2 (2) | H12B—C12—H12C | 109.5 |
N3—C2—N1 | 110.1 (2) | C11—C13—H13A | 109.5 |
N3—C2—C3 | 123.1 (2) | C11—C13—H13B | 109.5 |
N1—C2—C3 | 126.8 (2) | H13A—C13—H13B | 109.5 |
C7—C3—C4 | 117.8 (2) | C11—C13—H13C | 109.5 |
C7—C3—C2 | 120.8 (2) | H13A—C13—H13C | 109.5 |
C4—C3—C2 | 121.4 (2) | H13B—C13—H13C | 109.5 |
N5—C4—C3 | 121.3 (2) | C5—C14—H14A | 109.5 |
N5—C4—C15 | 114.7 (2) | C5—C14—H14B | 109.5 |
C3—C4—C15 | 124.0 (2) | H14A—C14—H14B | 109.5 |
N5—C5—C6 | 120.8 (3) | C5—C14—H14C | 109.5 |
N5—C5—C14 | 115.2 (3) | H14A—C14—H14C | 109.5 |
C6—C5—C14 | 124.0 (3) | H14B—C14—H14C | 109.5 |
C7—C6—C5 | 118.7 (2) | C4—C15—H15A | 109.5 |
C7—C6—C8 | 120.4 (2) | C4—C15—H15B | 109.5 |
C5—C6—C8 | 120.6 (2) | H15A—C15—H15B | 109.5 |
C6—C7—C3 | 120.2 (3) | C4—C15—H15C | 109.5 |
C6—C7—H7 | 119.9 | H15A—C15—H15C | 109.5 |
C3—C7—H7 | 119.9 | H15B—C15—H15C | 109.5 |
O1—C8—N6 | 120.2 (3) | C1—N1—C2 | 108.8 (2) |
O1—C8—C6 | 122.2 (3) | C1—N1—N4 | 125.6 (2) |
N6—C8—C6 | 117.5 (2) | C2—N1—N4 | 125.7 (2) |
N7—C9—C10 | 110.6 (3) | C1—N2—N3 | 114.0 (2) |
N7—C9—C12 | 120.8 (3) | C1—N2—H2 | 123.0 |
C10—C9—C12 | 128.6 (3) | N3—N2—H2 | 123.0 |
C11—C10—C9 | 107.7 (3) | C2—N3—N2 | 104.4 (2) |
C11—C10—H10 | 126.1 | N1—N4—H4A | 120.0 |
C9—C10—H10 | 126.1 | N1—N4—H4B | 120.0 |
C10—C11—N6 | 105.6 (3) | H4A—N4—H4B | 120.0 |
C10—C11—C13 | 129.8 (3) | C4—N5—C5 | 120.9 (2) |
N6—C11—C13 | 124.6 (3) | C11—N6—N7 | 111.0 (2) |
C9—C12—H12A | 109.5 | C11—N6—C8 | 127.8 (2) |
C9—C12—H12B | 109.5 | N7—N6—C8 | 121.2 (2) |
H12A—C12—H12B | 109.5 | C9—N7—N6 | 105.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···N7i | 0.86 | 2.11 | 2.873 (3) | 148 |
Symmetry code: (i) −x, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C15H17N7OS |
Mr | 343.42 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 273 |
a, b, c (Å) | 8.039 (5), 8.428 (5), 12.391 (8) |
α, β, γ (°) | 102.186 (7), 90.633 (8), 90.074 (8) |
V (Å3) | 820.5 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.20 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker APEX II CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.958, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4304, 2861, 2142 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.136, 1.03 |
No. of reflections | 2861 |
No. of parameters | 222 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.38, −0.45 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.
S1—C1 | 1.663 (3) | C8—O1 | 1.201 (3) |
C1—N2 | 1.333 (4) | C8—N6 | 1.398 (4) |
C1—N1 | 1.370 (3) | C9—N7 | 1.313 (3) |
C2—N3 | 1.301 (3) | N1—N4 | 1.390 (3) |
C2—N1 | 1.377 (3) | N2—N3 | 1.369 (3) |
C2—C3 | 1.463 (4) | N6—N7 | 1.385 (3) |
N2—C1—N1 | 102.8 (2) | C2—N1—N4 | 125.7 (2) |
N2—C1—S1 | 129.0 (2) | C11—N6—N7 | 111.0 (2) |
N1—C1—S1 | 128.2 (2) | C11—N6—C8 | 127.8 (2) |
N3—C2—N1 | 110.1 (2) | N7—N6—C8 | 121.2 (2) |
C1—N1—N4 | 125.6 (2) | C9—N7—N6 | 105.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···N7i | 0.86 | 2.11 | 2.873 (3) | 148 |
Symmetry code: (i) −x, −y+2, −z. |
Nitrogen-containing heterocycles compounds are well known natural products moieties which represent interesting biological activities and pharmacological properties (Pandeya et al., 2000; Soudi et al., 2005). For example, the 1,2,4-triazole nucleus with the nitrogen-bridged heterocycles always show antibacterial (Holla & Kalluraya, 1988) and antifungal (Prasad et al., 1989) properties. In addition, the substituted 1,2,4-triazol is a well established N-donor heterocyclic ligand (Elwahy & Abbas, 2000). More recently, it was reported that 1,2,4-triazole derivatives complexed with metal have higher biological activity (Tardito et al., 2007). Further more, the substituted 3,5-Dimethylpyrazoles contribute significant activities to diabetes (Soliman & Darwish,1983). These useful applications for the important class of nitrogen-containing heterocycles attracted our attention. Here, we report the synthesis and structure of a new multi-heterocyclic compound.
In the molecule of the title compound, (I), (Fig. 1), the C1—N2, C2—N3 bond distances [average =1.317 (3) Å] and N2—N3 bond distance [1.369 (3) Å] are in good agreement with those found for structures containing the 1,2,4-trizole ring Özbey et al., 2000; Bruno et al., 2003). The C=S double bond [1.663 (3) Å] is equal to the corresponding double bond (Xue et al., 2004). In the pyrazole ring, the bond distances between atoms are similar with those in the literature (Yang & Liu, 2005).
It is interesting to find that the three rings are not coplanar, due to steric hinderance. The angle between triazole plane and pyridine plane is 28.90 (3)°, whereas the angle between pyrazole plane and pyridine plane is 53.26 (9)°. Furthermore, the planes of triazole and pyrazole form a dihedral angle 55.55 (2)°. As a result of the torsional angle of the title compound, the steric hinderance has been reduced that make the compound more stable.